#------------------------------------------------------------------------------
#$Date: 2016-06-02 09:30:07 +0300 (Thu, 02 Jun 2016) $
#$Revision: 183252 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/90/7119003.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7119003
loop_
_publ_author_name
'Shubhanchi Nigam'
'Benjamin P. Burke'
'Laura H. Davies'
'Juozas Domarkas'
'Jennifer F. Wallis'
'Paul G. Waddell'
'Jennifer S. Waby'
'David M. Benoit'
'Anne-Marie Seymour'
'Christopher Cawthorne'
'Lee J. Higham'
'Stephen J. Archibald'
_publ_section_title
;
 Structurally optimised BODIPY derivatives for imaging of mitochondrial
 dysfunction in cancer and heart cells
;
_journal_name_full               Chem.Commun.
_journal_page_first              7114
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'Br, 3(C H Cl3), C41 H62 B F N2 P'
_chemical_formula_sum            'C44 H65 B Br Cl9 F N2 P'
_chemical_formula_weight         1081.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.127(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.7264(7)
_cell_length_b                   9.6603(2)
_cell_length_c                   23.4725(7)
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      65.8490
_cell_measurement_theta_min      3.7560
_cell_volume                     5297.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  ω    -34.00  68.00   1.00   20.00    --   41.59 -38.00   0.00  102
  2  ω     12.00 116.00   1.00   20.00    --   41.59  57.00 150.00  104
  3  ω      9.00  83.00   1.00   80.00    --   93.50 -94.00-180.00   74
  4  ω     16.00 124.00   1.00   80.00    --   93.50 -30.00  90.00  108
  5  ω      9.00  83.00   1.00   80.00    --   93.50 -94.00 120.00   74
  6  ω     10.00 155.00   1.00   80.00    --   93.50 -15.00 150.00  145
  7  ω     19.00  96.00   1.00   80.00    --   93.50-125.00  90.00   77
  8  ω     87.00 113.00   1.00   80.00    --   93.50 -93.00  96.24   26
  9  ω    103.00 160.00   1.00   80.00    --   93.50  45.00 -30.00   57
 10  ω     34.00  60.00   1.00   80.00    --   93.50 -89.00  44.59   26
 11  ω     76.00 123.00   1.00   80.00    --   93.50 -89.00  44.59   47
 12  ω     68.00 118.00   1.00   80.00    --   93.50 -45.00  30.00   50
 13  ω    105.00 131.00   1.00   80.00    --   93.50 125.00-180.00   26
 14  ω     16.00  72.00   1.00   80.00    --   93.50 -93.00  96.24   56
 15  ω     66.00 104.00   1.00   80.00    --   93.50 -61.00  90.00   38
 16  ω    146.00 172.00   1.00   80.00    --   93.50  77.00  60.00   26
 17  ω     21.00  53.00   1.00   80.00    --   93.50 -88.00-165.15   32
 18  ω     83.00 109.00   1.00   80.00    --   93.50 -88.00-165.15   26
 19  ω     80.00 127.00   1.00   80.00    --   93.50  77.00  60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0588324000
_diffrn_orient_matrix_UB_12      0.0013935000
_diffrn_orient_matrix_UB_13      0.0499408000
_diffrn_orient_matrix_UB_21      0.0293354000
_diffrn_orient_matrix_UB_22      0.0247429000
_diffrn_orient_matrix_UB_23      -0.0477761000
_diffrn_orient_matrix_UB_31      -0.0051258000
_diffrn_orient_matrix_UB_32      0.1575078000
_diffrn_orient_matrix_UB_33      0.0071235000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38266
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.983
_diffrn_reflns_theta_min         3.784
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.794
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.702
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         9392
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1035P)²+3.8861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.2101
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5931
_reflns_number_total             9392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08325g2.cif
_cod_data_source_block           ljh160010_3_fa
_cod_database_code               7119003
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C41 H62 B1 Br1 F1 N2 P1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl7B-C53B \\sim Cl7A-C53A
 with sigma of 0.02
 Cl9A-C53A \\sim Cl9B-C53B
 with sigma of 0.02
 Cl8A-C53A \\sim Cl8B-C53B
 with sigma of 0.02
 Cl7B-Cl9B \\sim Cl9A-Cl7A
 with sigma of 0.02
 Cl9A-Cl8A \\sim Cl9B-Cl8B
 with sigma of 0.02
 Cl8A-Cl7A \\sim Cl7B-Cl8B
 with sigma of 0.02
 F1C-C39C \\sim F1D-C39D \\sim F1A-C39A \\sim F1B-C39B
 with sigma of 0.02
 C43-C31B \\sim C43-C38C \\sim C39C-C38C
 with sigma of 0.02
 C37D-C31B \\sim C38D-C37D \\sim C39D-C38D
 with sigma of 0.02
 C37A-C31A \\sim C38A-C37A \\sim C39A-C38A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C53B) = Uanis(C53A)
Uanis(Cl8B) = Uanis(Cl8A)
Uanis(Cl7B) = Uanis(Cl7A)
Uanis(Cl9B) = Uanis(Cl9A)
Uanis(C31A) = Uanis(C32A) = Uanis(C33A) = Uanis(C34A) = Uanis(C35A) =
Uanis(C36A) = Uanis(C37A) = Uanis(C38A) = Uanis(C39A) = Uanis(F1A) =
Uanis(C37B) = Uanis(C38B) = Uanis(F1B) = Uanis(C37A) = Uanis(C39B)
Uanis(C43) = Uanis(C38C) = Uanis(C39C) = Uanis(F1C) = Uanis(C37D) = Uanis(C38D)
= Uanis(C39D) = Uanis(F1D) = Uanis(C31B) = Uanis(C32B) = Uanis(C33B) =
Uanis(C34B) = Uanis(C35B) = Uanis(C36B)
4. Same fragment restrains
{C37D, C38D, C39D, F1D} sigma for 1-2: 0.02, 1-3: 0.02
as
{C43, C38C, C39C, F1C}
{C37A, C38A, C39A, F1A} sigma for 1-2: 0.02, 1-3: 0.02
as
{C37B, C38B, C39B, F1B}
5. Others
 Fixed Sof: H31B(0.25) H31C(0.25) H31D(0.25) H31E(0.25) H31A(0.5) H31F(0.25)
 H31G(0.25) H31H(0.25) H31I(0.25) H31J(0.5) Cl7B(0.64946) Cl8B(0.64946)
 Cl9B(0.64946) C43(0.25) H43A(0.25) H43B(0.25) C38C(0.25) H38A(0.25) H38B(0.25)
 C39C(0.25) H39A(0.25) H39B(0.25) F1C(0.25) C32A(0.5) H32A(0.5) H32B(0.5)
 C33A(0.5) H33A(0.5) H33B(0.5) C34A(0.5) H34A(0.5) H34B(0.5) C35A(0.5)
 H35A(0.5) H35B(0.5) C36A(0.5) H36A(0.5) H36B(0.5) C53B(0.64946) H53B(0.64946)
 Cl7A(0.35054) Cl8A(0.35054) Cl9A(0.35054) C37A(0.25) H37A(0.25) H37B(0.25)
 C38A(0.25) H38C(0.25) H38D(0.25) C39A(0.25) H39C(0.25) H39D(0.25) F1A(0.25)
 C37D(0.25) H37C(0.25) H37D(0.25) C38D(0.25) H38E(0.25) H38F(0.25) C39D(0.25)
 H39E(0.25) H39F(0.25) F1D(0.25) C53A(0.35054) H53A(0.35054) C37B(0.25)
 H37E(0.25) H37F(0.25) C38B(0.25) H38G(0.25) H38H(0.25) C39B(0.25) H39G(0.25)
 H39H(0.25) F1B(0.25) C32B(0.5) H32C(0.5) H32D(0.5) C33B(0.5) H33C(0.5)
 H33D(0.5) C34B(0.5) H34C(0.5) H34D(0.5) C35B(0.5) H35C(0.5) H35D(0.5)
 C36B(0.5) H36C(0.5) H36D(0.5)
6.a Ternary CH refined with riding coordinates:
 C25(H25), C31A(H31A), C31B(H31J), C51(H51), C52(H52), C53B(H53B), C53A(H53A)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C31A(H31B,H31C), C31A(H31D,H31E),
 C31B(H31F,H31G), C31B(H31H,H31I), C43(H43A,H43B), C38C(H38A,H38B), C39C(H39A,
 H39B), C32A(H32A,H32B), C33A(H33A,H33B), C34A(H34A,H34B), C35A(H35A,H35B),
 C36A(H36A,H36B), C37A(H37A,H37B), C38A(H38C,H38D), C39A(H39C,H39D), C37D(H37C,
 H37D), C38D(H38E,H38F), C39D(H39E,H39F), C37B(H37E,H37F), C38B(H38G,H38H),
 C39B(H39G,H39H), C32B(H32C,H32D), C33B(H33C,H33D), C34B(H34C,H34D), C35B(H35C,
 H35D), C36B(H36C,H36D)
6.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C24(H24)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.303
_oxdiff_exptl_absorpt_empirical_full_min 0.567
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.13299(2) 0.20719(6) 0.36069(2) 0.0598(2) Uani 1 1 d . . . . .
Cl1 Cl 0.31058(7) 0.20849(16) 0.40500(7) 0.0739(4) Uani 1 1 d . . . . .
Cl2 Cl 0.30025(8) 0.05793(17) 0.50701(7) 0.0864(5) Uani 1 1 d . . . . .
Cl3 Cl 0.28370(6) 0.35213(16) 0.50060(7) 0.0694(4) Uani 1 1 d . . . . .
Cl4 Cl 0.08216(8) 0.2093(3) 0.16795(10) 0.1058(6) Uani 1 1 d . . . . .
Cl5 Cl 0.18978(12) 0.0684(3) 0.21452(15) 0.1360(10) Uani 1 1 d . . . . .
Cl6 Cl 0.18472(11) 0.3663(3) 0.20889(14) 0.1260(8) Uani 1 1 d . . . . .
P1 P 0.87390(6) 0.29043(15) 0.61549(6) 0.0539(3) Uani 1 1 d . . . . .
N1 N 0.53785(16) 0.3072(4) 0.60958(16) 0.0421(8) Uani 1 1 d . . . . .
N2 N 0.58986(16) 0.2997(4) 0.72167(16) 0.0414(8) Uani 1 1 d . . . . .
C1 C 0.5817(2) 0.3009(5) 0.5375(2) 0.0503(11) Uani 1 1 d . . . . .
C2 C 0.5230(2) 0.3053(5) 0.5096(2) 0.0508(12) Uani 1 1 d . . . . .
C3 C 0.4978(2) 0.3089(5) 0.5552(2) 0.0495(11) Uani 1 1 d . . . . .
C5 C 0.6027(2) 0.3012(5) 0.7819(2) 0.0459(11) Uani 1 1 d . . . . .
C6 C 0.6627(2) 0.2977(5) 0.8100(2) 0.0482(11) Uani 1 1 d . . . . .
C7 C 0.6874(2) 0.2943(5) 0.7653(2) 0.0474(11) Uani 1 1 d . . . . .
C8 C 0.64149(19) 0.2969(5) 0.6499(2) 0.0425(10) Uani 1 1 d . . . . .
C9 C 0.5912(2) 0.3009(5) 0.6007(2) 0.0445(10) Uani 1 1 d . . . . .
C10 C 0.64117(19) 0.2958(5) 0.7094(2) 0.0424(10) Uani 1 1 d . . . . .
C11 C 0.6252(2) 0.2948(7) 0.5053(2) 0.0626(14) Uani 1 1 d . . . . .
H11A H 0.6059 0.2964 0.4625 0.094 Uiso 1 1 calc GR . . . .
H11B H 0.6470 0.2110 0.5161 0.094 Uiso 1 1 calc GR . . . .
H11C H 0.6503 0.3730 0.5167 0.094 Uiso 1 1 calc GR . . . .
C12 C 0.4906(3) 0.2978(7) 0.4432(2) 0.0666(16) Uani 1 1 d . . . . .
H12A H 0.5136 0.3380 0.4210 0.080 Uiso 1 1 calc R . . . .
H12B H 0.4557 0.3519 0.4344 0.080 Uiso 1 1 calc R . . . .
C13 C 0.4754(3) 0.1508(8) 0.4223(3) 0.0818(19) Uani 1 1 d . . . . .
H13A H 0.4556 0.1500 0.3797 0.123 Uiso 1 1 calc GR . . . .
H13B H 0.4513 0.1120 0.4429 0.123 Uiso 1 1 calc GR . . . .
H13C H 0.5098 0.0968 0.4311 0.123 Uiso 1 1 calc GR . . . .
C14 C 0.4347(2) 0.3155(6) 0.5439(3) 0.0618(14) Uani 1 1 d . . . . .
H14A H 0.4169 0.2327 0.5235 0.093 Uiso 1 1 calc GR . . . .
H14B H 0.4190 0.3945 0.5192 0.093 Uiso 1 1 calc GR . . . .
H14C H 0.4276 0.3233 0.5816 0.093 Uiso 1 1 calc GR . . . .
C15 C 0.5603(2) 0.3030(6) 0.8143(2) 0.0561(12) Uani 1 1 d . . . . .
H15A H 0.5639 0.3879 0.8365 0.084 Uiso 1 1 calc GR . . . .
H15B H 0.5672 0.2261 0.8417 0.084 Uiso 1 1 calc GR . . . .
H15C H 0.5224 0.2962 0.7858 0.084 Uiso 1 1 calc GR . . . .
C16 C 0.6917(2) 0.2941(6) 0.8772(2) 0.0602(13) Uani 1 1 d . . . . .
H16A H 0.6672 0.3384 0.8966 0.072 Uiso 1 1 calc R . . . .
H16B H 0.7270 0.3467 0.8873 0.072 Uiso 1 1 calc R . . . .
C17 C 0.7052(3) 0.1482(7) 0.9016(3) 0.0750(17) Uani 1 1 d . . . . .
H17A H 0.7324 0.1068 0.8855 0.112 Uiso 1 1 calc GR . . . .
H17B H 0.6707 0.0941 0.8900 0.112 Uiso 1 1 calc GR . . . .
H17C H 0.7210 0.1512 0.9448 0.112 Uiso 1 1 calc GR . . . .
C18 C 0.7504(2) 0.2911(7) 0.7763(2) 0.0616(14) Uani 1 1 d . . . . .
H18A H 0.7705 0.2923 0.8189 0.092 Uiso 1 1 calc GR . . . .
H18B H 0.7612 0.3705 0.7579 0.092 Uiso 1 1 calc GR . . . .
H18C H 0.7600 0.2083 0.7591 0.092 Uiso 1 1 calc GR . . . .
C19 C 0.6973(2) 0.2936(5) 0.6387(2) 0.0444(10) Uani 1 1 d . . . . .
C20 C 0.7236(2) 0.1686(5) 0.6354(2) 0.0492(11) Uani 1 1 d . . . . .
H20 H 0.7059 0.0859 0.6393 0.059 Uiso 1 1 calc R . . . .
C21 C 0.7760(2) 0.1667(5) 0.6262(2) 0.0497(12) Uani 1 1 d . . . . .
H21 H 0.7935 0.0826 0.6239 0.060 Uiso 1 1 calc R . . . .
C22 C 0.8030(2) 0.2908(5) 0.6204(2) 0.0488(11) Uani 1 1 d . . . . .
C23 C 0.7766(2) 0.4173(5) 0.6242(2) 0.0491(11) Uani 1 1 d . . . . .
H23 H 0.7943 0.5004 0.6207 0.059 Uiso 1 1 calc R . . . .
C24 C 0.7239(2) 0.4168(5) 0.6332(2) 0.0486(11) Uani 1 1 d . . . . .
H24 H 0.7061 0.5004 0.6355 0.058 Uiso 1 1 calc R . . . .
C25 C 0.9237(2) 0.2925(6) 0.6923(3) 0.0618(14) Uani 1 1 d . . . . .
H25 H 0.9625 0.2873 0.6899 0.074 Uiso 1 1 calc R . . . .
C26 C 0.9196(3) 0.4269(8) 0.7244(3) 0.0809(19) Uani 1 1 d . . . . .
H26A H 0.9270 0.5046 0.7019 0.097 Uiso 1 1 calc R . . . .
H26B H 0.8812 0.4370 0.7264 0.097 Uiso 1 1 calc R . . . .
C27 C 0.9625(3) 0.4275(10) 0.7877(4) 0.103(3) Uani 1 1 d . . . . .
H27A H 1.0010 0.4252 0.7857 0.123 Uiso 1 1 calc R . . . .
H27B H 0.9582 0.5118 0.8083 0.123 Uiso 1 1 calc R . . . .
C28 C 0.9530(4) 0.3034(13) 0.8224(4) 0.122(4) Uani 1 1 d . . . . .
H28A H 0.9153 0.3094 0.8265 0.147 Uiso 1 1 calc R . . . .
H28B H 0.9811 0.3040 0.8625 0.147 Uiso 1 1 calc R . . . .
C29 C 0.9579(4) 0.1674(10) 0.7906(4) 0.107(3) Uani 1 1 d . . . . .
H29A H 0.9964 0.1580 0.7889 0.129 Uiso 1 1 calc R . . . .
H29B H 0.9507 0.0899 0.8135 0.129 Uiso 1 1 calc R . . . .
C30 C 0.9153(3) 0.1648(8) 0.7274(3) 0.083(2) Uani 1 1 d . . . . .
H30A H 0.8766 0.1642 0.7292 0.100 Uiso 1 1 calc R . . . .
H30B H 0.9206 0.0813 0.7069 0.100 Uiso 1 1 calc R . . . .
C31A C 0.8840(3) 0.1375(8) 0.5764(3) 0.0812(11) Uani 1 1 d D . . . .
H31B H 0.9184 0.1507 0.5658 0.097 Uiso 0.25 1 calc R . P A 2
H31C H 0.8913 0.0609 0.6046 0.097 Uiso 0.25 1 calc R . P A 2
H31D H 0.9248 0.1351 0.5827 0.097 Uiso 0.25 1 calc R . P B 3
H31E H 0.8767 0.0612 0.5998 0.097 Uiso 0.25 1 calc R . P B 3
H31A H 0.8735 0.0565 0.5956 0.097 Uiso 0.5 1 calc R . P C 1
C31B C 0.8837(3) 0.4441(8) 0.5762(3) 0.0820(12) Uani 1 1 d D . . . .
H31F H 0.8465 0.4597 0.5462 0.098 Uiso 0.25 1 calc R . P D 1
H31G H 0.8884 0.5177 0.6056 0.098 Uiso 0.25 1 calc R . P D 1
H31H H 0.8538 0.4424 0.5372 0.098 Uiso 0.25 1 calc R . P E 2
H31I H 0.8753 0.5219 0.5980 0.098 Uiso 0.25 1 calc R . P E 2
H31J H 0.8752 0.5252 0.5969 0.098 Uiso 0.5 1 calc R . P F 3
C49 C 0.4952(2) 0.1588(5) 0.6767(2) 0.0534(12) Uani 1 1 d . . . . .
H49A H 0.4607 0.1519 0.6428 0.080 Uiso 1 1 calc GR . . . .
H49B H 0.4860 0.1570 0.7134 0.080 Uiso 1 1 calc GR . . . .
H49C H 0.5199 0.0823 0.6763 0.080 Uiso 1 1 calc GR . . . .
C50 C 0.4947(2) 0.4429(5) 0.6804(2) 0.0532(12) Uani 1 1 d . . . . .
H50A H 0.5186 0.5214 0.6808 0.080 Uiso 1 1 calc GR . . . .
H50B H 0.4865 0.4395 0.7177 0.080 Uiso 1 1 calc GR . . . .
H50C H 0.4595 0.4512 0.6474 0.080 Uiso 1 1 calc GR . . . .
C51 C 0.2753(2) 0.1989(6) 0.4583(3) 0.0639(15) Uani 1 1 d . . . . .
H51 H 0.2343 0.1853 0.4369 0.077 Uiso 1 1 calc R . . . .
C52 C 0.1515(3) 0.2134(8) 0.2197(3) 0.0794(18) Uani 1 1 d . . . . .
H52 H 0.1486 0.2160 0.2603 0.095 Uiso 1 1 calc R . . . .
B4 B 0.5275(2) 0.3022(6) 0.6728(2) 0.0447(12) Uani 1 1 d . . . . .
Cl7B Cl 0.6679(2) 0.7447(14) 0.8429(3) 0.1050(16) Uani 0.6495 1 d D . P G 1
Cl8B Cl 0.6445(3) 0.6487(10) 0.7208(4) 0.0903(17) Uani 0.6495 1 d D . P G 1
Cl9B Cl 0.644(3) 0.9398(10) 0.7448(9) 0.0946(9) Uani 0.6495 1 d D . P G 1
C43 C 0.9237(11) 0.478(3) 0.5456(11) 0.0820(12) Uani 0.25 1 d D . P H 1
H43A H 0.9254 0.4016 0.5195 0.098 Uiso 0.25 1 calc R . P H 1
H43B H 0.9614 0.4888 0.5753 0.098 Uiso 0.25 1 calc R . P H 1
C38C C 0.9092(12) 0.606(3) 0.5090(11) 0.0820(12) Uani 0.25 1 d D . P H 1
H38A H 0.8994 0.6784 0.5324 0.098 Uiso 0.25 1 calc R . P H 1
H38B H 0.9423 0.6359 0.4987 0.098 Uiso 0.25 1 calc R . P H 1
C39C C 0.8608(13) 0.582(3) 0.4532(10) 0.0820(12) Uani 0.25 1 d D . P H 1
H39A H 0.8266 0.5713 0.4645 0.098 Uiso 0.25 1 calc R . P H 1
H39B H 0.8557 0.6659 0.4291 0.098 Uiso 0.25 1 calc R . P H 1
F1C F 0.8629(8) 0.4774(17) 0.4182(7) 0.0820(12) Uani 0.25 1 d D . P H 1
C32A C 0.9400(6) 0.1143(15) 0.5718(7) 0.0812(11) Uani 0.5 1 d . . P I 1
H32A H 0.9676 0.1091 0.6122 0.097 Uiso 0.5 1 calc R . P I 1
H32B H 0.9502 0.1932 0.5519 0.097 Uiso 0.5 1 calc R . P I 1
C33A C 0.9446(7) -0.0135(16) 0.5384(6) 0.0812(11) Uani 0.5 1 d . . P I 1
H33A H 0.9844 -0.0312 0.5426 0.097 Uiso 0.5 1 calc R . P I 1
H33B H 0.9301 -0.0922 0.5546 0.097 Uiso 0.5 1 calc R . P I 1
C34A C 0.9106(7) 0.0064(18) 0.4739(8) 0.0812(11) Uani 0.5 1 d . . P I 1
H34A H 0.9163 -0.0713 0.4502 0.097 Uiso 0.5 1 calc R . P I 1
H34B H 0.9227 0.0901 0.4587 0.097 Uiso 0.5 1 calc R . P I 1
C35A C 0.8469(7) 0.0173(17) 0.4690(7) 0.0812(11) Uani 0.5 1 d . . P I 1
H35A H 0.8355 -0.0649 0.4859 0.097 Uiso 0.5 1 calc R . P I 1
H35B H 0.8233 0.0238 0.4269 0.097 Uiso 0.5 1 calc R . P I 1
C36A C 0.8375(8) 0.1494(18) 0.5040(7) 0.0812(11) Uani 0.5 1 d . . P I 1
H36A H 0.7984 0.1529 0.5041 0.097 Uiso 0.5 1 calc R . P I 1
H36B H 0.8451 0.2328 0.4849 0.097 Uiso 0.5 1 calc R . P I 1
C53B C 0.6306(4) 0.7763(11) 0.7681(4) 0.070(2) Uani 0.6495 1 d D . P G 1
H53B H 0.5897 0.7715 0.7632 0.084 Uiso 0.6495 1 calc R . P G 1
Cl7A Cl 0.6844(6) 0.744(3) 0.8410(6) 0.1050(16) Uani 0.3505 1 d D . P J 2
Cl8A Cl 0.6269(7) 0.658(2) 0.7189(9) 0.0903(17) Uani 0.3505 1 d D . P J 2
Cl9A Cl 0.644(6) 0.9474(18) 0.7465(16) 0.0946(9) Uani 0.3505 1 d D . P J 2
C37A C 0.8391(11) 0.096(3) 0.5226(11) 0.0812(11) Uani 0.25 1 d D . P I 2
H37A H 0.8317 0.1735 0.4950 0.097 Uiso 0.25 1 calc R . P I 2
H37B H 0.8049 0.0826 0.5337 0.097 Uiso 0.25 1 calc R . P I 2
C38A C 0.8450(13) -0.027(3) 0.4886(13) 0.0812(11) Uani 0.25 1 d D . P I 2
H38C H 0.8420 -0.1087 0.5112 0.097 Uiso 0.25 1 calc R . P I 2
H38D H 0.8134 -0.0286 0.4508 0.097 Uiso 0.25 1 calc R . P I 2
C39A C 0.8979(13) -0.033(3) 0.4756(15) 0.0812(11) Uani 0.25 1 d D . P I 2
H39C H 0.9300 -0.0303 0.5128 0.097 Uiso 0.25 1 calc R . P I 2
H39D H 0.8998 -0.1185 0.4547 0.097 Uiso 0.25 1 calc R . P I 2
F1A F 0.8997(7) 0.0727(16) 0.4419(7) 0.0812(11) Uani 0.25 1 d D . P I 2
C37D C 0.9362(9) 0.479(4) 0.5646(13) 0.0820(12) Uani 0.25 1 d D . P H 2
H37C H 0.9469 0.4013 0.5444 0.098 Uiso 0.25 1 calc R . P H 2
H37D H 0.9663 0.4916 0.6030 0.098 Uiso 0.25 1 calc R . P H 2
C38D C 0.9332(13) 0.604(3) 0.5277(11) 0.0820(12) Uani 0.25 1 d D . P H 2
H38E H 0.9210 0.6821 0.5466 0.098 Uiso 0.25 1 calc R . P H 2
H38F H 0.9711 0.6252 0.5262 0.098 Uiso 0.25 1 calc R . P H 2
C39D C 0.8939(15) 0.588(3) 0.4666(11) 0.0820(12) Uani 0.25 1 d D . P H 2
H39E H 0.8557 0.5812 0.4694 0.098 Uiso 0.25 1 calc R . P H 2
H39F H 0.8952 0.6732 0.4452 0.098 Uiso 0.25 1 calc R . P H 2
F1D F 0.8996(8) 0.4844(16) 0.4317(7) 0.0820(12) Uani 0.25 1 d D . P H 2
C53A C 0.6702(7) 0.7813(18) 0.7660(7) 0.070(2) Uani 0.3505 1 d D . P J 2
H53A H 0.7070 0.7776 0.7588 0.084 Uiso 0.3505 1 calc R . P J 2
C37B C 0.8614(14) 0.102(3) 0.5231(15) 0.0812(11) Uani 0.25 1 d D . P I 3
H37E H 0.8618 0.1813 0.4982 0.097 Uiso 0.25 1 calc R . P I 3
H37F H 0.8215 0.0815 0.5176 0.097 Uiso 0.25 1 calc R . P I 3
C38B C 0.8838(13) -0.015(3) 0.4986(9) 0.0812(11) Uani 0.25 1 d D . P I 3
H38G H 0.9235 0.0036 0.5027 0.097 Uiso 0.25 1 calc R . P I 3
H38H H 0.8831 -0.0968 0.5223 0.097 Uiso 0.25 1 calc R . P I 3
C39B C 0.8527(12) -0.044(2) 0.4359(10) 0.0812(11) Uani 0.25 1 d D . P I 3
H39G H 0.8694 -0.1232 0.4223 0.097 Uiso 0.25 1 calc R . P I 3
H39H H 0.8130 -0.0649 0.4307 0.097 Uiso 0.25 1 calc R . P I 3
F1B F 0.8563(7) 0.0671(16) 0.4049(7) 0.0812(11) Uani 0.25 1 d D . P I 3
C32B C 0.8509(7) 0.4532(16) 0.5134(6) 0.0820(12) Uani 0.5 1 d . . P H 3
H32C H 0.8106 0.4428 0.5083 0.098 Uiso 0.5 1 calc R . P H 3
H32D H 0.8619 0.3787 0.4917 0.098 Uiso 0.5 1 calc R . P H 3
C33B C 0.8606(7) 0.5904(17) 0.4877(7) 0.0820(12) Uani 0.5 1 d . . P H 3
H33C H 0.8531 0.6653 0.5116 0.098 Uiso 0.5 1 calc R . P H 3
H33D H 0.8346 0.5998 0.4467 0.098 Uiso 0.5 1 calc R . P H 3
C34B C 0.9251(7) 0.5987(18) 0.4881(8) 0.0820(12) Uani 0.5 1 d . . P H 3
H34C H 0.9328 0.5244 0.4640 0.098 Uiso 0.5 1 calc R . P H 3
H34D H 0.9318 0.6863 0.4713 0.098 Uiso 0.5 1 calc R . P H 3
C35B C 0.9630(7) 0.5860(16) 0.5517(7) 0.0820(12) Uani 0.5 1 d . . P H 3
H35C H 0.9567 0.6644 0.5746 0.098 Uiso 0.5 1 calc R . P H 3
H35D H 1.0026 0.5885 0.5530 0.098 Uiso 0.5 1 calc R . P H 3
C36B C 0.9520(7) 0.4489(18) 0.5817(7) 0.0820(12) Uani 0.5 1 d . . P H 3
H36C H 0.9759 0.4462 0.6237 0.098 Uiso 0.5 1 calc R . P H 3
H36D H 0.9614 0.3696 0.5614 0.098 Uiso 0.5 1 calc R . P H 3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0278
-1 0 2 0.0113
1 0 -2 0.0073
1 2 1 0.2115
0 -2 -1 0.2222
-1 0 0 0.0288
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C22 P1 C25 107.1(2) . .
C22 P1 C31A 109.6(3) . .
C22 P1 C31B 109.2(3) . .
C31A P1 C25 110.6(3) . .
C31A P1 C31B 110.5(3) . .
C31B P1 C25 109.7(3) . .
C3 N1 C9 107.3(4) . .
C3 N1 B4 126.7(4) . .
C9 N1 B4 125.8(4) . .
C5 N2 C10 107.5(4) . .
C5 N2 B4 126.6(4) . .
C10 N2 B4 125.8(4) . .
C2 C1 C9 106.4(4) . .
C2 C1 C11 125.1(4) . .
C9 C1 C11 128.5(4) . .
C1 C2 C3 107.3(4) . .
C1 C2 C12 127.6(5) . .
C3 C2 C12 125.0(5) . .
N1 C3 C2 110.7(4) . .
N1 C3 C14 125.1(5) . .
C2 C3 C14 124.2(4) . .
N2 C5 C6 109.9(4) . .
N2 C5 C15 125.2(4) . .
C6 C5 C15 124.8(4) . .
C5 C6 C16 123.8(5) . .
C7 C6 C5 107.8(4) . .
C7 C6 C16 128.3(5) . .
C6 C7 C10 106.1(4) . .
C6 C7 C18 124.6(4) . .
C10 C7 C18 129.3(5) . .
C9 C8 C10 122.1(4) . .
C9 C8 C19 118.9(4) . .
C10 C8 C19 119.0(4) . .
N1 C9 C1 108.2(4) . .
C8 C9 N1 120.4(4) . .
C8 C9 C1 131.4(5) . .
N2 C10 C7 108.6(4) . .
N2 C10 C8 120.7(4) . .
C8 C10 C7 130.7(4) . .
C1 C11 H11A 109.5 . .
C1 C11 H11B 109.5 . .
C1 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C2 C12 H12A 109.2 . .
C2 C12 H12B 109.2 . .
C2 C12 C13 111.9(5) . .
H12A C12 H12B 107.9 . .
C13 C12 H12A 109.2 . .
C13 C12 H12B 109.2 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C3 C14 H14A 109.5 . .
C3 C14 H14B 109.5 . .
C3 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C5 C15 H15A 109.5 . .
C5 C15 H15B 109.5 . .
C5 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C6 C16 H16A 109.0 . .
C6 C16 H16B 109.0 . .
C6 C16 C17 112.9(5) . .
H16A C16 H16B 107.8 . .
C17 C16 H16A 109.0 . .
C17 C16 H16B 109.0 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C7 C18 H18A 109.5 . .
C7 C18 H18B 109.5 . .
C7 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 C8 120.5(4) . .
C20 C19 C24 119.8(4) . .
C24 C19 C8 119.6(4) . .
C19 C20 H20 120.0 . .
C21 C20 C19 120.1(5) . .
C21 C20 H20 120.0 . .
C20 C21 H21 119.8 . .
C20 C21 C22 120.3(5) . .
C22 C21 H21 119.8 . .
C21 C22 P1 120.7(4) . .
C21 C22 C23 119.6(5) . .
C23 C22 P1 119.4(4) . .
C22 C23 H23 120.4 . .
C24 C23 C22 119.1(5) . .
C24 C23 H23 120.4 . .
C19 C24 H24 119.5 . .
C23 C24 C19 121.0(5) . .
C23 C24 H24 119.5 . .
P1 C25 H25 107.4 . .
C26 C25 P1 111.5(4) . .
C26 C25 H25 107.4 . .
C26 C25 C30 112.2(6) . .
C30 C25 P1 110.8(4) . .
C30 C25 H25 107.4 . .
C25 C26 H26A 109.6 . .
C25 C26 H26B 109.6 . .
H26A C26 H26B 108.1 . .
C27 C26 C25 110.4(6) . .
C27 C26 H26A 109.6 . .
C27 C26 H26B 109.6 . .
C26 C27 H27A 109.7 . .
C26 C27 H27B 109.7 . .
H27A C27 H27B 108.2 . .
C28 C27 C26 110.0(7) . .
C28 C27 H27A 109.7 . .
C28 C27 H27B 109.7 . .
C27 C28 H28A 109.3 . .
C27 C28 H28B 109.3 . .
C27 C28 C29 111.5(7) . .
H28A C28 H28B 108.0 . .
C29 C28 H28A 109.3 . .
C29 C28 H28B 109.3 . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 108.1 . .
C30 C29 C28 110.5(7) . .
C30 C29 H29A 109.5 . .
C30 C29 H29B 109.5 . .
C25 C30 H30A 109.7 . .
C25 C30 H30B 109.7 . .
C29 C30 C25 109.8(6) . .
C29 C30 H30A 109.7 . .
C29 C30 H30B 109.7 . .
H30A C30 H30B 108.2 . .
P1 C31A H31B 107.6 . .
P1 C31A H31C 107.6 . .
P1 C31A H31D 104.6 . .
P1 C31A H31E 104.6 . .
P1 C31A H31A 108.5 . .
H31B C31A H31C 107.0 . .
H31D C31A H31E 105.7 . .
C32A C31A P1 117.5(8) . .
C32A C31A H31A 108.5 . .
C32A C31A C36A 106.6(9) . .
C36A C31A P1 106.9(7) . .
C36A C31A H31A 108.5 . .
C37A C31A P1 118.8(13) . .
C37A C31A H31B 107.6 . .
C37A C31A H31C 107.6 . .
C37B C31A P1 130.7(15) . .
C37B C31A H31D 104.6 . .
C37B C31A H31E 104.6 . .
P1 C31B H31F 104.2 . .
P1 C31B H31G 104.2 . .
P1 C31B H31H 106.2 . .
P1 C31B H31I 106.2 . .
P1 C31B H31J 108.6 . .
H31F C31B H31G 105.5 . .
H31H C31B H31I 106.4 . .
C43 C31B P1 132.3(13) . .
C43 C31B H31F 104.2 . .
C43 C31B H31G 104.2 . .
C37D C31B P1 124.4(13) . .
C37D C31B H31H 106.2 . .
C37D C31B H31I 106.2 . .
C32B C31B P1 116.8(8) . .
C32B C31B H31J 108.6 . .
C32B C31B C36B 107.3(9) . .
C36B C31B P1 106.7(7) . .
C36B C31B H31J 108.6 . .
H49A C49 H49B 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
B4 C49 H49A 109.5 . .
B4 C49 H49B 109.5 . .
B4 C49 H49C 109.5 . .
H50A C50 H50B 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
B4 C50 H50A 109.5 . .
B4 C50 H50B 109.5 . .
B4 C50 H50C 109.5 . .
Cl1 C51 Cl2 110.8(3) . .
Cl1 C51 Cl3 111.4(3) . .
Cl1 C51 H51 108.3 . .
Cl2 C51 Cl3 109.5(3) . .
Cl2 C51 H51 108.3 . .
Cl3 C51 H51 108.3 . .
Cl4 C52 Cl6 108.6(4) . .
Cl4 C52 H52 107.9 . .
Cl5 C52 Cl4 111.8(4) . .
Cl5 C52 Cl6 112.6(4) . .
Cl5 C52 H52 107.9 . .
Cl6 C52 H52 107.9 . .
N1 B4 N2 105.0(4) . .
N1 B4 C49 108.2(4) . .
N1 B4 C50 108.5(4) . .
N2 B4 C49 109.0(4) . .
N2 B4 C50 109.6(4) . .
C49 B4 C50 116.0(4) . .
C31B C43 H43A 108.7 . .
C31B C43 H43B 108.7 . .
C31B C43 C38C 114(2) . .
H43A C43 H43B 107.6 . .
C38C C43 H43A 108.7 . .
C38C C43 H43B 108.7 . .
C43 C38C H38A 109.4 . .
C43 C38C H38B 109.4 . .
H38A C38C H38B 108.0 . .
C39C C38C C43 111.1(19) . .
C39C C38C H38A 109.4 . .
C39C C38C H38B 109.4 . .
C38C C39C H39A 107.5 . .
C38C C39C H39B 107.5 . .
H39A C39C H39B 107.0 . .
F1C C39C C38C 119(2) . .
F1C C39C H39A 107.5 . .
F1C C39C H39B 107.5 . .
C31A C32A H32A 108.7 . .
C31A C32A H32B 108.7 . .
C31A C32A C33A 114.1(12) . .
H32A C32A H32B 107.6 . .
C33A C32A H32A 108.7 . .
C33A C32A H32B 108.7 . .
C32A C33A H33A 110.0 . .
C32A C33A H33B 110.0 . .
H33A C33A H33B 108.4 . .
C34A C33A C32A 108.4(13) . .
C34A C33A H33A 110.0 . .
C34A C33A H33B 110.0 . .
C33A C34A H34A 110.1 . .
C33A C34A H34B 110.1 . .
C33A C34A C35A 107.9(12) . .
H34A C34A H34B 108.4 . .
C35A C34A H34A 110.1 . .
C35A C34A H34B 110.1 . .
C34A C35A H35A 109.7 . .
C34A C35A H35B 109.7 . .
C34A C35A C36A 109.7(14) . .
H35A C35A H35B 108.2 . .
C36A C35A H35A 109.7 . .
C36A C35A H35B 109.7 . .
C31A C36A H36A 110.3 . .
C31A C36A H36B 110.3 . .
C35A C36A C31A 107.3(12) . .
C35A C36A H36A 110.3 . .
C35A C36A H36B 110.3 . .
H36A C36A H36B 108.5 . .
Cl7B C53B Cl8B 111.6(6) . .
Cl7B C53B Cl9B 112.9(10) . .
Cl7B C53B H53B 107.4 . .
Cl8B C53B H53B 107.4 . .
Cl9B C53B Cl8B 109.9(17) . .
Cl9B C53B H53B 107.4 . .
C31A C37A H37A 107.0 . .
C31A C37A H37B 107.0 . .
C31A C37A C38A 121(2) . .
H37A C37A H37B 106.7 . .
C38A C37A H37A 107.0 . .
C38A C37A H37B 107.0 . .
C37A C38A H38C 108.7 . .
C37A C38A H38D 108.7 . .
H38C C38A H38D 107.6 . .
C39A C38A C37A 114(2) . .
C39A C38A H38C 108.7 . .
C39A C38A H38D 108.7 . .
C38A C39A H39C 110.1 . .
C38A C39A H39D 110.1 . .
H39C C39A H39D 108.4 . .
F1A C39A C38A 108.2(19) . .
F1A C39A H39C 110.1 . .
F1A C39A H39D 110.1 . .
C31B C37D H37C 108.5 . .
C31B C37D H37D 108.5 . .
C31B C37D C38D 115(2) . .
H37C C37D H37D 107.5 . .
C38D C37D H37C 108.5 . .
C38D C37D H37D 108.5 . .
C37D C38D H38E 109.2 . .
C37D C38D H38F 109.2 . .
H38E C38D H38F 107.9 . .
C39D C38D C37D 112.2(19) . .
C39D C38D H38E 109.2 . .
C39D C38D H38F 109.2 . .
C38D C39D H39E 107.0 . .
C38D C39D H39F 107.0 . .
H39E C39D H39F 106.8 . .
F1D C39D C38D 121(2) . .
F1D C39D H39E 107.0 . .
F1D C39D H39F 107.0 . .
Cl7A C53A Cl8A 112.7(11) . .
Cl7A C53A Cl9A 113.3(18) . .
Cl7A C53A H53A 106.2 . .
Cl8A C53A H53A 106.2 . .
Cl9A C53A Cl8A 112(2) . .
Cl9A C53A H53A 106.2 . .
C31A C37B H37E 107.2 . .
C31A C37B H37F 107.2 . .
C31A C37B C38B 121(3) . .
H37E C37B H37F 106.8 . .
C38B C37B H37E 107.2 . .
C38B C37B H37F 107.2 . .
C37B C38B H38G 108.7 . .
C37B C38B H38H 108.7 . .
H38G C38B H38H 107.6 . .
C39B C38B C37B 114(2) . .
C39B C38B H38G 108.7 . .
C39B C38B H38H 108.7 . .
C38B C39B H39G 110.3 . .
C38B C39B H39H 110.3 . .
H39G C39B H39H 108.6 . .
F1B C39B C38B 107.1(19) . .
F1B C39B H39G 110.3 . .
F1B C39B H39H 110.3 . .
C31B C32B H32C 109.5 . .
C31B C32B H32D 109.5 . .
C31B C32B C33B 110.8(12) . .
H32C C32B H32D 108.1 . .
C33B C32B H32C 109.5 . .
C33B C32B H32D 109.5 . .
C32B C33B H33C 109.8 . .
C32B C33B H33D 109.8 . .
C32B C33B C34B 109.4(13) . .
H33C C33B H33D 108.2 . .
C34B C33B H33C 109.8 . .
C34B C33B H33D 109.8 . .
C33B C34B H34C 110.2 . .
C33B C34B H34D 110.2 . .
H34C C34B H34D 108.5 . .
C35B C34B C33B 107.6(14) . .
C35B C34B H34C 110.2 . .
C35B C34B H34D 110.2 . .
C34B C35B H35C 109.2 . .
C34B C35B H35D 109.2 . .
C34B C35B C36B 112.1(13) . .
H35C C35B H35D 107.9 . .
C36B C35B H35C 109.2 . .
C36B C35B H35D 109.2 . .
C31B C36B H36C 110.1 . .
C31B C36B H36D 110.1 . .
C35B C36B C31B 108.2(12) . .
C35B C36B H36C 110.1 . .
C35B C36B H36D 110.1 . .
H36C C36B H36D 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C51 1.747(7) .
Cl2 C51 1.755(6) .
Cl3 C51 1.756(6) .
Cl4 C52 1.747(7) .
Cl5 C52 1.716(8) .
Cl6 C52 1.748(8) .
P1 C22 1.795(5) .
P1 C25 1.821(6) .
P1 C31A 1.800(8) .
P1 C31B 1.805(7) .
N1 C3 1.335(6) .
N1 C9 1.403(6) .
N1 B4 1.588(7) .
N2 C5 1.343(6) .
N2 C10 1.391(6) .
N2 B4 1.592(6) .
C1 C2 1.385(7) .
C1 C9 1.424(7) .
C1 C11 1.503(8) .
C2 C3 1.405(7) .
C2 C12 1.502(7) .
C3 C14 1.496(7) .
C5 C6 1.413(7) .
C5 C15 1.484(7) .
C6 C7 1.376(7) .
C6 C16 1.504(7) .
C7 C10 1.431(6) .
C7 C18 1.493(8) .
C8 C9 1.392(6) .
C8 C10 1.400(7) .
C8 C19 1.488(7) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.509(10) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C17 1.518(9) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 C20 1.385(7) .
C19 C24 1.387(7) .
C20 H20 0.9300 .
C20 C21 1.382(7) .
C21 H21 0.9300 .
C21 C22 1.400(8) .
C22 C23 1.401(7) .
C23 H23 0.9300 .
C23 C24 1.386(7) .
C24 H24 0.9300 .
C25 H25 0.9800 .
C25 C26 1.521(9) .
C25 C30 1.535(10) .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C26 C27 1.517(9) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C27 C28 1.510(14) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 C29 1.535(14) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C30 1.513(10) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C31A H31B 0.9700 .
C31A H31C 0.9700 .
C31A H31D 0.9700 .
C31A H31E 0.9700 .
C31A H31A 0.9800 .
C31A C32A 1.441(16) .
C31A C36A 1.714(18) .
C31A C37A 1.44(2) .
C31A C37B 1.24(3) .
C31B H31F 0.9700 .
C31B H31G 0.9700 .
C31B H31H 0.9700 .
C31B H31I 0.9700 .
C31B H31J 0.9800 .
C31B C43 1.438(16) .
C31B C37D 1.451(17) .
C31B C32B 1.433(16) .
C31B C36B 1.653(17) .
C49 H49A 0.9600 .
C49 H49B 0.9600 .
C49 H49C 0.9600 .
C49 B4 1.616(8) .
C50 H50A 0.9600 .
C50 H50B 0.9600 .
C50 H50C 0.9600 .
C50 B4 1.622(8) .
C51 H51 0.9800 .
C52 H52 0.9800 .
Cl7B C53B 1.721(10) .
Cl8B C53B 1.766(11) .
Cl9B C53B 1.74(3) .
C43 H43A 0.9700 .
C43 H43B 0.9700 .
C43 C38C 1.477(18) .
C38C H38A 0.9700 .
C38C H38B 0.9700 .
C38C C39C 1.474(18) .
C39C H39A 0.9700 .
C39C H39B 0.9700 .
C39C F1C 1.316(19) .
C32A H32A 0.9700 .
C32A H32B 0.9700 .
C32A C33A 1.49(2) .
C33A H33A 0.9700 .
C33A H33B 0.9700 .
C33A C34A 1.49(2) .
C34A H34A 0.9700 .
C34A H34B 0.9700 .
C34A C35A 1.55(2) .
C35A H35A 0.9700 .
C35A H35B 0.9700 .
C35A C36A 1.58(2) .
C36A H36A 0.9700 .
C36A H36B 0.9700 .
C53B H53B 0.9800 .
Cl7A C53A 1.716(15) .
Cl8A C53A 1.736(16) .
Cl9A C53A 1.74(4) .
C37A H37A 0.9700 .
C37A H37B 0.9700 .
C37A C38A 1.461(19) .
C38A H38C 0.9700 .
C38A H38D 0.9700 .
C38A C39A 1.44(2) .
C39A H39C 0.9700 .
C39A H39D 0.9700 .
C39A F1A 1.30(2) .
C37D H37C 0.9700 .
C37D H37D 0.9700 .
C37D C38D 1.477(18) .
C38D H38E 0.9700 .
C38D H38F 0.9700 .
C38D C39D 1.454(18) .
C39D H39E 0.9700 .
C39D H39F 0.9700 .
C39D F1D 1.330(19) .
C53A H53A 0.9800 .
C37B H37E 0.9700 .
C37B H37F 0.9700 .
C37B C38B 1.46(2) .
C38B H38G 0.9700 .
C38B H38H 0.9700 .
C38B C39B 1.45(2) .
C39B H39G 0.9700 .
C39B H39H 0.9700 .
C39B F1B 1.318(19) .
C32B H32C 0.9700 .
C32B H32D 0.9700 .
C32B C33B 1.51(2) .
C33B H33C 0.9700 .
C33B H33D 0.9700 .
C33B C34B 1.59(2) .
C34B H34C 0.9700 .
C34B H34D 0.9700 .
C34B C35B 1.48(2) .
C35B H35C 0.9700 .
C35B H35D 0.9700 .
C35B C36B 1.57(2) .
C36B H36C 0.9700 .
C36B H36D 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
P1 C22 C23 C24 -174.5(4) . . . .
P1 C25 C26 C27 -178.6(6) . . . .
P1 C25 C30 C29 178.9(6) . . . .
P1 C31A C32A C33A -179.5(9) . . . .
P1 C31A C36A C35A 178.9(9) . . . .
P1 C31A C37A C38A 179.4(18) . . . .
P1 C31A C37B C38B 168.6(19) . . . .
P1 C31B C43 C38C 168.3(13) . . . .
P1 C31B C37D C38D 175.6(16) . . . .
P1 C31B C32B C33B 176.4(9) . . . .
P1 C31B C36B C35B -176.4(9) . . . .
N2 C5 C6 C7 0.1(6) . . . .
N2 C5 C6 C16 -178.2(5) . . . .
C1 C2 C3 N1 0.1(6) . . . .
C1 C2 C3 C14 179.4(5) . . . .
C1 C2 C12 C13 90.6(7) . . . .
C2 C1 C9 N1 -0.8(6) . . . .
C2 C1 C9 C8 179.7(5) . . . .
C3 N1 C9 C1 0.8(5) . . . .
C3 N1 C9 C8 -179.6(4) . . . .
C3 N1 B4 N2 179.2(4) . . . .
C3 N1 B4 C49 62.9(6) . . . .
C3 N1 B4 C50 -63.8(6) . . . .
C3 C2 C12 C13 -84.9(7) . . . .
C5 N2 C10 C7 0.2(5) . . . .
C5 N2 C10 C8 -178.5(4) . . . .
C5 N2 B4 N1 177.0(4) . . . .
C5 N2 B4 C49 -67.2(6) . . . .
C5 N2 B4 C50 60.7(6) . . . .
C5 C6 C7 C10 0.0(5) . . . .
C5 C6 C7 C18 179.6(5) . . . .
C5 C6 C16 C17 93.7(7) . . . .
C6 C7 C10 N2 -0.2(5) . . . .
C6 C7 C10 C8 178.4(5) . . . .
C7 C6 C16 C17 -84.2(7) . . . .
C8 C19 C20 C21 -178.7(4) . . . .
C8 C19 C24 C23 178.4(4) . . . .
C9 N1 C3 C2 -0.5(6) . . . .
C9 N1 C3 C14 -179.9(5) . . . .
C9 N1 B4 N2 3.9(6) . . . .
C9 N1 B4 C49 -112.4(5) . . . .
C9 N1 B4 C50 120.9(5) . . . .
C9 C1 C2 C3 0.4(6) . . . .
C9 C1 C2 C12 -175.7(5) . . . .
C9 C8 C10 N2 -0.4(7) . . . .
C9 C8 C10 C7 -178.8(5) . . . .
C9 C8 C19 C20 -93.1(6) . . . .
C9 C8 C19 C24 88.6(6) . . . .
C10 N2 C5 C6 -0.2(5) . . . .
C10 N2 C5 C15 -179.0(5) . . . .
C10 N2 B4 N1 -2.8(6) . . . .
C10 N2 B4 C49 112.9(5) . . . .
C10 N2 B4 C50 -119.2(5) . . . .
C10 C8 C9 N1 1.4(7) . . . .
C10 C8 C9 C1 -179.1(5) . . . .
C10 C8 C19 C20 86.9(6) . . . .
C10 C8 C19 C24 -91.3(6) . . . .
C11 C1 C2 C3 179.4(5) . . . .
C11 C1 C2 C12 3.3(9) . . . .
C11 C1 C9 N1 -179.7(5) . . . .
C11 C1 C9 C8 0.7(9) . . . .
C12 C2 C3 N1 176.3(5) . . . .
C12 C2 C3 C14 -4.3(9) . . . .
C15 C5 C6 C7 178.9(5) . . . .
C15 C5 C6 C16 0.6(8) . . . .
C16 C6 C7 C10 178.2(5) . . . .
C16 C6 C7 C18 -2.2(9) . . . .
C18 C7 C10 N2 -179.7(5) . . . .
C18 C7 C10 C8 -1.1(9) . . . .
C19 C8 C9 N1 -178.6(4) . . . .
C19 C8 C9 C1 0.9(8) . . . .
C19 C8 C10 N2 179.6(4) . . . .
C19 C8 C10 C7 1.2(8) . . . .
C19 C20 C21 C22 0.1(7) . . . .
C20 C19 C24 C23 0.1(7) . . . .
C20 C21 C22 P1 174.2(4) . . . .
C20 C21 C22 C23 0.4(7) . . . .
C21 C22 C23 C24 -0.6(7) . . . .
C22 P1 C25 C26 -65.6(5) . . . .
C22 P1 C25 C30 60.1(5) . . . .
C22 P1 C31A C32A -175.7(8) . . . .
C22 P1 C31A C36A 64.6(8) . . . .
C22 P1 C31A C37A 43.9(16) . . . .
C22 P1 C31A C37B 67(2) . . . .
C22 P1 C31B C43 -160.0(18) . . . .
C22 P1 C31B C37D 179.2(18) . . . .
C22 P1 C31B C32B -67.9(9) . . . .
C22 P1 C31B C36B 172.2(7) . . . .
C22 C23 C24 C19 0.4(7) . . . .
C24 C19 C20 C21 -0.4(7) . . . .
C25 P1 C22 C21 -86.6(5) . . . .
C25 P1 C22 C23 87.3(5) . . . .
C25 P1 C31A C32A -57.7(9) . . . .
C25 P1 C31A C36A -177.4(7) . . . .
C25 P1 C31A C37A 161.8(16) . . . .
C25 P1 C31A C37B -175(2) . . . .
C25 P1 C31B C43 82.9(18) . . . .
C25 P1 C31B C37D 62.1(18) . . . .
C25 P1 C31B C32B 175.0(8) . . . .
C25 P1 C31B C36B 55.0(8) . . . .
C25 C26 C27 C28 -56.7(9) . . . .
C26 C25 C30 C29 -55.8(8) . . . .
C26 C27 C28 C29 57.9(9) . . . .
C27 C28 C29 C30 -57.9(10) . . . .
C28 C29 C30 C25 55.4(10) . . . .
C30 C25 C26 C27 56.5(8) . . . .
C31A P1 C22 C21 33.6(5) . . . .
C31A P1 C22 C23 -152.6(4) . . . .
C31A P1 C25 C26 174.9(5) . . . .
C31A P1 C25 C30 -59.4(5) . . . .
C31A P1 C31B C43 -39.3(19) . . . .
C31A P1 C31B C37D -60.1(19) . . . .
C31A P1 C31B C32B 52.8(9) . . . .
C31A P1 C31B C36B -67.2(8) . . . .
C31A C32A C33A C34A 69.0(15) . . . .
C31A C37A C38A C39A -49(4) . . . .
C31A C37B C38B C39B 180(3) . . . .
C31B P1 C22 C21 154.8(4) . . . .
C31B P1 C22 C23 -31.4(5) . . . .
C31B P1 C25 C26 52.8(5) . . . .
C31B P1 C25 C30 178.5(5) . . . .
C31B P1 C31A C32A 63.9(9) . . . .
C31B P1 C31A C36A -55.8(8) . . . .
C31B P1 C31A C37A -76.5(16) . . . .
C31B P1 C31A C37B -54(2) . . . .
C31B C43 C38C C39C -74(3) . . . .
C31B C37D C38D C39D -65(4) . . . .
C31B C32B C33B C34B 66.7(16) . . . .
B4 N1 C3 C2 -176.6(5) . . . .
B4 N1 C3 C14 4.0(8) . . . .
B4 N1 C9 C1 176.9(4) . . . .
B4 N1 C9 C8 -3.5(7) . . . .
B4 N2 C5 C6 179.9(4) . . . .
B4 N2 C5 C15 1.1(7) . . . .
B4 N2 C10 C7 -179.9(4) . . . .
B4 N2 C10 C8 1.4(7) . . . .
C43 C38C C39C F1C -52(4) . . . .
C32A C31A C36A C35A 52.4(14) . . . .
C32A C33A C34A C35A -66.1(16) . . . .
C33A C34A C35A C36A 63.4(17) . . . .
C34A C35A C36A C31A -55.0(15) . . . .
C36A C31A C32A C33A -59.7(14) . . . .
C37A C38A C39A F1A -62(4) . . . .
C37D C38D C39D F1D -56(4) . . . .
C37B C38B C39B F1B 61(3) . . . .
C32B C31B C36B C35B 57.7(14) . . . .
C32B C33B C34B C35B -60.3(17) . . . .
C33B C34B C35B C36B 57.5(17) . . . .
C34B C35B C36B C31B -56.5(16) . . . .
C36B C31B C32B C33B -64.0(14) . . . .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0003 -0.0001 0.0001 0.0589 0.0293 -0.0051
-1.0007 0.0002 2.0007 0.0410 -0.1249 0.0194
1.0007 -0.0002 -2.0007 -0.0410 0.1249 -0.0194
0.9975 1.9998 0.9993 0.1114 0.0310 0.3170
0.0028 -1.9999 -0.9993 -0.0525 -0.0017 -0.3221
-1.0003 0.0001 -0.0001 -0.0589 -0.0293 0.0051
