#------------------------------------------------------------------------------
#$Date: 2024-12-06 20:12:19 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/72/7717232.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_7717232
loop_
_publ_author_name
'Wu, Jingyun'
'Stevens, Michael A.'
'Gardiner, Michael G.'
'Colebatch, Annie L.'
_publ_section_title
;
 Ruthenium, copper and ruthenium-copper complexes of an unsymmetrical
 phosphino pyridyl 1,8-naphthyridine PNNN ligand.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18037
_journal_page_last               18046
_journal_paper_doi               10.1039/d4dt02755h
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         '2(C22 H28 N3 P), C H Cl3'
_chemical_formula_sum            'C45 H57 Cl3 N6 P2'
_chemical_formula_weight         850.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.9800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.4963(2)
_cell_length_b                   6.17950(10)
_cell_length_c                   20.5648(3)
_cell_measurement_reflns_used    8407
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.5740
_cell_measurement_theta_min      5.0060
_cell_volume                     2235.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00 -50.00   1.00    5.25    --  -36.95 125.00-180.00   26
  2  ω    -44.00 -16.00   1.00    5.25    --  -36.95 125.00-180.00   28
  3  ω    -21.00  44.00   1.00    5.25    --   36.95 -38.00   0.00   65
  4  ω     29.00  63.00   1.00    5.25    --   36.95-125.00  30.00   34
  5  ω    -32.00  51.00   1.00    5.25    --   36.95 -38.00-150.00   83
  6  ω     59.00  89.00   1.00    5.25    --   36.95-125.00 -30.00   30
  7  ω     11.00  37.00   1.00    5.25    --   36.95 -99.00-180.00   26
  8  ω     45.00  76.00   1.00    5.25    --   36.95 -99.00-180.00   31
  9  ω     35.00  64.00   1.00    5.25    --   36.95 -99.00  90.00   29
 10  ω     29.00  93.00   1.00    5.25    --   36.95  38.00-150.00   64
 11  ω     42.00  75.00   1.00   21.00    --  111.00-111.00 -30.00   33
 12  ω    101.00 127.00   1.00   21.00    --  111.00 -38.00 -60.00   26
 13  ω     92.00 118.00   1.00   21.00    --  111.00 -77.00   0.00   26
 14  ω     81.00 109.00   1.00   21.00    --  111.00-111.00 -30.00   28
 15  ω     79.00 107.00   1.00   21.00    --  111.00-111.00   0.00   28
 16  ω     60.00 100.00   1.00   21.00    --  111.00 -38.00 -60.00   40
 17  ω    108.00 148.00   1.00   21.00    --  111.00  64.00  30.00   40
 18  ω     51.00  79.00   1.00   21.00    --  111.00-111.00-120.00   28
 19  ω     43.00 102.00   1.00   21.00    --  111.00 -92.00   0.00   59
 20  ω     96.00 124.00   1.00   21.00    --  111.00 -25.00   0.00   28
 21  ω     63.00 104.00   1.00   21.00    --  111.00 -92.00-120.00   41
 22  ω     43.00  73.00   1.00   21.00    --  111.00-111.00   0.00   30
 23  ω     69.00 101.00   1.00   21.00    --  111.00 -92.00-180.00   32
 24  ω    104.00 137.00   1.00   21.00    --  111.00  77.00 -90.00   33
 25  ω    152.00 177.00   1.00   21.00    --  111.00  77.00 -90.00   25
 26  ω     49.00  80.00   1.00   21.00    --  111.00 -77.00   0.00   31
 27  ω     48.00  77.00   1.00   21.00    --  111.00 -25.00   0.00   29
 28  ω    109.00 171.00   1.00   21.00    --  111.00 111.00  26.00   62
 29  ω     44.00  88.00   1.00   21.00    --  111.00 -50.00  60.00   44
 30  ω    124.00 177.00   1.00   21.00    --  111.00  25.00 120.00   53
 31  ω    115.00 142.00   1.00   21.00    --  111.00  77.00 120.00   27
 32  ω     81.00 106.00   1.00   21.00    --  111.00 -92.00-150.00   25
 33  ω     91.00 124.00   1.00   21.00    --  111.00 -77.00 -90.00   33
 34  ω     52.00 114.00   1.00   21.00    --  111.00 -50.00  90.00   62
 35  ω     76.00 101.00   1.00   21.00    --  111.00 -92.00  30.00   25
 36  ω     64.00  90.00   1.00   21.00    --  111.00 -92.00  90.00   26
 37  ω     99.00 129.00   1.00   21.00    --  111.00  64.00 -90.00   30
 38  ω     99.00 137.00   1.00   21.00    --  111.00 -77.00 -46.81   38
 39  ω     60.00  85.00   1.00   21.00    --  111.00 -77.00 -46.81   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218592000
_diffrn_orient_matrix_UB_12      -0.2291290000
_diffrn_orient_matrix_UB_13      0.0168179000
_diffrn_orient_matrix_UB_21      -0.0083078000
_diffrn_orient_matrix_UB_22      0.0842397000
_diffrn_orient_matrix_UB_23      0.0678460000
_diffrn_orient_matrix_UB_31      -0.0843448000
_diffrn_orient_matrix_UB_32      0.0510866000
_diffrn_orient_matrix_UB_33      -0.0363386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15589
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.856
_diffrn_reflns_theta_min         3.863
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       needle
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.065(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7852
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0358
_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)+(0.0554P)²+0.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_full    0.741
_reflns_Friedel_fraction_max     0.706
_reflns_number_gt                7325
_reflns_number_total             7852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02755h2.cif
_cod_data_source_block           jw105
_cod_depositor_comments
'Adding full bibliography for 7717232--7717238.cif.'
_cod_database_code               7717232
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N P Cl Ru'
_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.
;
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.336
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10A(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C6A(H6A), C20A(H20A), C3(H3), C3A(H3A), C7A(H7A),
 C4A(H4A), C20(H20), C21A(H21A), C22(H22), C23(H23), C22A(H22A), C21(H21),
 C23A(H23A)
2.d Idealised Me refined as rotating group:
 C14(H14D,H14E,H14F), C13(H13D,H13E,H13F), C15(H15D,H15E,H15F), C17(H17D,H17E,
 H17F), C18(H18D,H18E,H18F), C18A(H18A,H18B,H18C), C16(H16D,H16E,H16F),
 C14A(H14A,H14B,H14C), C13A(H13A,H13B,H13C), C15A(H15A,H15B,H15C), C16A(H16A,
 H16B,H16C), C17A(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2022-06-02
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.654
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
P1A P 0.68783(3) 0.14444(11) 1.01113(4) 0.02695(14) Uani 1 1 d . . . . .
P1 P 0.82072(3) 0.47618(11) 0.53675(3) 0.02601(14) Uani 1 1 d . . . . .
Cl3 Cl 0.50588(4) -0.06281(17) 0.24762(4) 0.0492(2) Uani 1 1 d . . . . .
Cl1 Cl 0.58810(5) 0.34234(16) 0.26339(5) 0.0506(2) Uani 1 1 d . . . . .
Cl2 Cl 0.65909(5) -0.04074(18) 0.33668(5) 0.0571(2) Uani 1 1 d . . . . .
N1 N 0.59965(11) 0.4177(4) 0.44762(11) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.47617(11) 0.4503(4) 0.37620(11) 0.0242(4) Uani 1 1 d . . . . .
N2A N 0.94792(11) 0.1218(4) 0.88418(12) 0.0262(4) Uani 1 1 d . . . . .
N1A N 0.86536(12) 0.0910(4) 0.94799(13) 0.0276(5) Uani 1 1 d . . . . .
N3 N 0.28180(14) 0.5754(5) 0.28387(14) 0.0378(6) Uani 1 1 d . . . . .
N3A N 1.09704(14) 0.2267(5) 0.81134(14) 0.0390(6) Uani 1 1 d . . . . .
C8 C 0.41344(14) 0.5665(5) 0.35223(14) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.65904(13) 0.5001(4) 0.49479(13) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.46746(14) 0.8841(5) 0.41534(14) 0.0275(5) Uani 1 1 d . . . . .
H6 H 0.464631 1.028470 0.427049 0.033 Uiso 1 1 calc R U . . .
C9 C 0.53707(13) 0.5466(4) 0.42242(13) 0.0224(5) Uani 1 1 d . . . . .
C8A C 0.99629(14) 0.2394(5) 0.86270(14) 0.0263(5) Uani 1 1 d . . . . .
C19A C 1.03676(14) 0.1252(5) 0.82030(14) 0.0293(5) Uani 1 1 d . . . . .
C5A C 0.92364(13) 0.4427(4) 0.94298(13) 0.0257(5) Uani 1 1 d . . . . .
C5 C 0.53508(14) 0.7643(5) 0.44369(14) 0.0245(5) Uani 1 1 d . . . . .
C19 C 0.34594(13) 0.4594(5) 0.30267(13) 0.0277(5) Uani 1 1 d . . . . .
C9A C 0.91216(13) 0.2217(4) 0.92513(14) 0.0248(5) Uani 1 1 d . . . . .
C2A C 0.83183(13) 0.1769(5) 0.98980(14) 0.0279(5) Uani 1 1 d . . . . .
C10 C 0.72551(13) 0.3525(5) 0.52597(14) 0.0266(5) Uani 1 1 d . . . . .
H10C H 0.720269 0.224853 0.497421 0.032 Uiso 1 1 calc R U . . .
H10D H 0.723520 0.305587 0.570404 0.032 Uiso 1 1 calc R U . . .
C7 C 0.40666(14) 0.7844(5) 0.37068(14) 0.0277(5) Uani 1 1 d . . . . .
H7 H 0.361149 0.858669 0.352467 0.033 Uiso 1 1 calc R U . . .
C4 C 0.60015(14) 0.8482(5) 0.49326(14) 0.0274(5) Uani 1 1 d . . . . .
H4 H 0.601210 0.990942 0.507861 0.033 Uiso 1 1 calc R U . . .
C6A C 0.97411(15) 0.5633(5) 0.91744(15) 0.0301(6) Uani 1 1 d . . . . .
H6A H 0.981683 0.710100 0.927098 0.036 Uiso 1 1 calc R U . . .
C20A C 1.01270(15) -0.0772(5) 0.79230(14) 0.0323(6) Uani 1 1 d . . . . .
H20A H 0.969682 -0.141398 0.798200 0.039 Uiso 1 1 calc R U . . .
C3 C 0.66118(14) 0.7164(5) 0.51920(14) 0.0278(5) Uani 1 1 d . . . . .
H3 H 0.704053 0.767225 0.552700 0.033 Uiso 1 1 calc R U . . .
C12 C 0.84201(14) 0.3806(5) 0.45776(15) 0.0315(6) Uani 1 1 d . . . . .
C10A C 0.78317(14) 0.0292(5) 1.01719(17) 0.0325(6) Uani 1 1 d . . . . .
H10A H 0.809934 -0.002766 1.064726 0.039 Uiso 1 1 calc R U . . .
H10B H 0.776039 -0.106124 0.992111 0.039 Uiso 1 1 calc R U . . .
C3A C 0.84079(14) 0.3980(5) 1.01091(15) 0.0319(6) Uani 1 1 d . . . . .
H3A H 0.816325 0.451306 1.040871 0.038 Uiso 1 1 calc R U . . .
C12A C 0.62695(17) 0.0296(6) 0.92733(16) 0.0375(7) Uani 1 1 d . . . . .
C11A C 0.66825(16) 0.0088(5) 1.08567(16) 0.0341(6) Uani 1 1 d . . . . .
C11 C 0.88021(15) 0.3277(5) 0.61526(15) 0.0318(6) Uani 1 1 d . . . . .
C7A C 1.01152(14) 0.4609(5) 0.87843(14) 0.0298(5) Uani 1 1 d . . . . .
H7A H 1.046355 0.535360 0.862498 0.036 Uiso 1 1 calc R U . . .
C4A C 0.88553(14) 0.5300(5) 0.98668(15) 0.0305(6) Uani 1 1 d . . . . .
H4A H 0.890876 0.675502 0.998771 0.037 Uiso 1 1 calc R U . . .
C20 C 0.35090(15) 0.2531(5) 0.27819(16) 0.0335(6) Uani 1 1 d . . . . .
H20 H 0.396390 0.176679 0.292739 0.040 Uiso 1 1 calc R U . . .
C14 C 0.96437(15) 0.3619(7) 0.62191(17) 0.0436(8) Uani 1 1 d . . . . .
H14D H 0.977968 0.271381 0.589577 0.065 Uiso 1 1 calc R U . . .
H14E H 0.995105 0.325005 0.667387 0.065 Uiso 1 1 calc R U . . .
H14F H 0.972686 0.510783 0.612924 0.065 Uiso 1 1 calc R U . . .
C13 C 0.86375(16) 0.4437(6) 0.67546(15) 0.0391(7) Uani 1 1 d . . . . .
H13D H 0.874537 0.595280 0.673930 0.059 Uiso 1 1 calc R U . . .
H13E H 0.895216 0.383589 0.717774 0.059 Uiso 1 1 calc R U . . .
H13F H 0.811230 0.424693 0.672180 0.059 Uiso 1 1 calc R U . . .
C15 C 0.86494(19) 0.0852(6) 0.61905(18) 0.0433(8) Uani 1 1 d . . . . .
H15D H 0.812173 0.062778 0.614208 0.065 Uiso 1 1 calc R U . . .
H15E H 0.895516 0.029423 0.662391 0.065 Uiso 1 1 calc R U . . .
H15F H 0.877559 0.011276 0.582937 0.065 Uiso 1 1 calc R U . . .
C21A C 1.05367(19) -0.1818(6) 0.75551(16) 0.0393(7) Uani 1 1 d . . . . .
H21A H 1.039268 -0.318293 0.736999 0.047 Uiso 1 1 calc R U . . .
C17 C 0.85028(17) 0.1357(6) 0.45013(17) 0.0401(7) Uani 1 1 d . . . . .
H17D H 0.896658 0.087045 0.482783 0.060 Uiso 1 1 calc R U . . .
H17E H 0.851406 0.104043 0.404749 0.060 Uiso 1 1 calc R U . . .
H17F H 0.807958 0.062801 0.458078 0.060 Uiso 1 1 calc R U . . .
C18 C 0.77487(16) 0.4667(7) 0.39852(15) 0.0409(7) Uani 1 1 d . . . . .
H18D H 0.729439 0.389623 0.397398 0.061 Uiso 1 1 calc R U . . .
H18E H 0.785357 0.446037 0.356043 0.061 Uiso 1 1 calc R U . . .
H18F H 0.767989 0.618142 0.405220 0.061 Uiso 1 1 calc R U . . .
C22 C 0.22084(16) 0.2828(7) 0.21133(17) 0.0413(7) Uani 1 1 d . . . . .
H22 H 0.177039 0.228441 0.179830 0.050 Uiso 1 1 calc R U . . .
C18A C 0.65969(19) 0.1278(7) 0.87373(17) 0.0449(7) Uani 1 1 d . . . . .
H18A H 0.667493 0.280233 0.881889 0.067 Uiso 1 1 calc R U . . .
H18B H 0.624711 0.104823 0.828861 0.067 Uiso 1 1 calc R U . . .
H18C H 0.707305 0.059589 0.876966 0.067 Uiso 1 1 calc R U . . .
C23 C 0.22133(16) 0.4849(7) 0.23875(17) 0.0442(8) Uani 1 1 d . . . . .
H23 H 0.176511 0.564638 0.225024 0.053 Uiso 1 1 calc R U . . .
C22A C 1.11647(18) -0.0788(7) 0.74690(16) 0.0424(7) Uani 1 1 d . . . . .
H22A H 1.145389 -0.144605 0.722650 0.051 Uiso 1 1 calc R U . . .
C21 C 0.28690(17) 0.1610(6) 0.23144(17) 0.0410(7) Uani 1 1 d . . . . .
H21 H 0.288539 0.022356 0.214338 0.049 Uiso 1 1 calc R U . . .
C16 C 0.91410(16) 0.4944(7) 0.45347(18) 0.0441(8) Uani 1 1 d . . . . .
H16D H 0.909832 0.647213 0.459880 0.066 Uiso 1 1 calc R U . . .
H16E H 0.920121 0.468314 0.409409 0.066 Uiso 1 1 calc R U . . .
H16F H 0.957464 0.438961 0.488426 0.066 Uiso 1 1 calc R U . . .
C14A C 0.5875(2) 0.0681(9) 1.0845(2) 0.0576(11) Uani 1 1 d . . . . .
H14A H 0.580185 0.221435 1.078146 0.086 Uiso 1 1 calc R U . . .
H14B H 0.580124 0.026769 1.127012 0.086 Uiso 1 1 calc R U . . .
H14C H 0.551411 -0.006599 1.047575 0.086 Uiso 1 1 calc R U . . .
C24 C 0.57418(17) 0.1047(6) 0.30433(16) 0.0372(6) Uani 1 1 d . . . . .
H24 H 0.555581 0.143912 0.342514 0.045 Uiso 1 1 calc R U . . .
C13A C 0.72328(19) 0.1168(7) 1.14948(17) 0.0457(8) Uani 1 1 d . . . . .
H13A H 0.774606 0.078215 1.152930 0.068 Uiso 1 1 calc R U . . .
H13B H 0.711875 0.068262 1.189571 0.068 Uiso 1 1 calc R U . . .
H13C H 0.717608 0.271129 1.145654 0.068 Uiso 1 1 calc R U . . .
C15A C 0.6804(2) -0.2363(7) 1.0925(2) 0.0521(9) Uani 1 1 d . . . . .
H15A H 0.643005 -0.307779 1.055732 0.078 Uiso 1 1 calc R U . . .
H15B H 0.675456 -0.283748 1.135370 0.078 Uiso 1 1 calc R U . . .
H15C H 0.730291 -0.271092 1.090628 0.078 Uiso 1 1 calc R U . . .
C23A C 1.13519(17) 0.1240(7) 0.77519(18) 0.0452(8) Uani 1 1 d . . . . .
H23A H 1.177011 0.193378 0.768614 0.054 Uiso 1 1 calc R U . . .
C16A C 0.54565(18) 0.1249(9) 0.9127(2) 0.0565(10) Uani 1 1 d . . . . .
H16A H 0.521899 0.062569 0.943771 0.085 Uiso 1 1 calc R U . . .
H16B H 0.516010 0.092006 0.866588 0.085 Uiso 1 1 calc R U . . .
H16C H 0.548853 0.279033 0.918873 0.085 Uiso 1 1 calc R U . . .
C17A C 0.6199(2) -0.2157(7) 0.9201(2) 0.0584(10) Uani 1 1 d . . . . .
H17A H 0.669355 -0.277597 0.927012 0.088 Uiso 1 1 calc R U . . .
H17B H 0.587535 -0.251682 0.875124 0.088 Uiso 1 1 calc R U . . .
H17C H 0.598524 -0.272239 0.953572 0.088 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.3639 0.7018 '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_
_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
_geom_angle_publ_flag
C10A P1A C12A 101.70(15) . . ?
C10A P1A C11A 101.02(14) . . ?
C11A P1A C12A 111.57(15) . . ?
C10 P1 C12 102.12(12) . . ?
C10 P1 C11 100.47(13) . . ?
C12 P1 C11 111.33(13) . . ?
C2 N1 C9 117.9(2) . . ?
C8 N2 C9 117.6(2) . . ?
C8A N2A C9A 117.5(2) . . ?
C2A N1A C9A 117.5(2) . . ?
C23 N3 C19 117.0(3) . . ?
C23A N3A C19A 117.4(3) . . ?
N2 C8 C19 117.7(3) . . ?
N2 C8 C7 123.8(2) . . ?
C7 C8 C19 118.5(2) . . ?
N1 C2 C10 117.6(2) . . ?
N1 C2 C3 123.1(2) . . ?
C3 C2 C10 119.2(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C7 C6 C5 118.9(3) . . ?
N1 C9 C5 122.3(2) . . ?
N2 C9 N1 115.4(2) . . ?
N2 C9 C5 122.2(2) . . ?
N2A C8A C19A 116.5(3) . . ?
N2A C8A C7A 124.0(3) . . ?
C7A C8A C19A 119.4(3) . . ?
N3A C19A C8A 116.6(3) . . ?
N3A C19A C20A 122.5(3) . . ?
C20A C19A C8A 120.9(3) . . ?
C9A C5A C6A 118.4(3) . . ?
C4A C5A C9A 118.1(3) . . ?
C4A C5A C6A 123.5(3) . . ?
C6 C5 C9 118.2(2) . . ?
C4 C5 C6 123.6(3) . . ?
C4 C5 C9 118.2(2) . . ?
N3 C19 C8 116.0(3) . . ?
N3 C19 C20 122.8(3) . . ?
C20 C19 C8 121.2(2) . . ?
N2A C9A N1A 115.0(2) . . ?
N2A C9A C5A 122.2(3) . . ?
N1A C9A C5A 122.8(3) . . ?
N1A C2A C10A 117.1(3) . . ?
N1A C2A C3A 123.4(3) . . ?
C3A C2A C10A 119.5(3) . . ?
P1 C10 H10C 108.6 . . ?
P1 C10 H10D 108.6 . . ?
C2 C10 P1 114.72(19) . . ?
C2 C10 H10C 108.6 . . ?
C2 C10 H10D 108.6 . . ?
H10C C10 H10D 107.6 . . ?
C8 C7 H7 120.4 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.4 . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5A C6A H6A 120.5 . . ?
C7A C6A C5A 119.0(3) . . ?
C7A C6A H6A 120.5 . . ?
C19A C20A H20A 120.4 . . ?
C21A C20A C19A 119.1(3) . . ?
C21A C20A H20A 120.4 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C17 C12 P1 116.9(2) . . ?
C17 C12 C18 110.0(3) . . ?
C17 C12 C16 109.3(3) . . ?
C18 C12 P1 104.0(2) . . ?
C16 C12 P1 108.8(2) . . ?
C16 C12 C18 107.4(3) . . ?
P1A C10A H10A 108.8 . . ?
P1A C10A H10B 108.8 . . ?
C2A C10A P1A 113.8(2) . . ?
C2A C10A H10A 108.8 . . ?
C2A C10A H10B 108.8 . . ?
H10A C10A H10B 107.7 . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A C2A 119.3(3) . . ?
C4A C3A H3A 120.4 . . ?
C18A C12A P1A 104.5(2) . . ?
C18A C12A C16A 106.5(3) . . ?
C16A C12A P1A 107.7(2) . . ?
C17A C12A P1A 118.2(3) . . ?
C17A C12A C18A 111.3(3) . . ?
C17A C12A C16A 108.0(3) . . ?
C14A C11A P1A 108.3(2) . . ?
C14A C11A C13A 107.1(3) . . ?
C13A C11A P1A 105.0(2) . . ?
C15A C11A P1A 117.2(2) . . ?
C15A C11A C14A 110.7(3) . . ?
C15A C11A C13A 108.1(3) . . ?
C14 C11 P1 108.5(2) . . ?
C14 C11 C13 108.1(2) . . ?
C13 C11 P1 104.7(2) . . ?
C15 C11 P1 116.8(2) . . ?
C15 C11 C14 109.2(3) . . ?
C15 C11 C13 109.2(3) . . ?
C8A C7A H7A 120.6 . . ?
C6A C7A C8A 118.8(3) . . ?
C6A C7A H7A 120.6 . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A C5A 119.0(3) . . ?
C3A C4A H4A 120.5 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C11 C14 H14D 109.5 . . ?
C11 C14 H14E 109.5 . . ?
C11 C14 H14F 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C11 C13 H13D 109.5 . . ?
C11 C13 H13E 109.5 . . ?
C11 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C11 C15 H15D 109.5 . . ?
C11 C15 H15E 109.5 . . ?
C11 C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C20A C21A H21A 120.7 . . ?
C22A C21A C20A 118.6(3) . . ?
C22A C21A H21A 120.7 . . ?
C12 C17 H17D 109.5 . . ?
C12 C17 H17E 109.5 . . ?
C12 C17 H17F 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C12 C18 H18D 109.5 . . ?
C12 C18 H18E 109.5 . . ?
C12 C18 H18F 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C23 C22 H22 120.7 . . ?
C23 C22 C21 118.7(3) . . ?
C21 C22 H22 120.7 . . ?
C12A C18A H18A 109.5 . . ?
C12A C18A H18B 109.5 . . ?
C12A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N3 C23 C22 124.4(3) . . ?
N3 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
C21A C22A H22A 120.8 . . ?
C23A C22A C21A 118.4(3) . . ?
C23A C22A H22A 120.8 . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.8(3) . . ?
C22 C21 H21 121.1 . . ?
C12 C16 H16D 109.5 . . ?
C12 C16 H16E 109.5 . . ?
C12 C16 H16F 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
Cl3 C24 H24 108.5 . . ?
Cl1 C24 Cl3 110.82(17) . . ?
Cl1 C24 Cl2 111.40(18) . . ?
Cl1 C24 H24 108.5 . . ?
Cl2 C24 Cl3 108.95(19) . . ?
Cl2 C24 H24 108.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C15A H15A 109.5 . . ?
C11A C15A H15B 109.5 . . ?
C11A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
N3A C23A C22A 124.1(3) . . ?
N3A C23A H23A 118.0 . . ?
C22A C23A H23A 118.0 . . ?
C12A C16A H16A 109.5 . . ?
C12A C16A H16B 109.5 . . ?
C12A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C12A C17A H17A 109.5 . . ?
C12A C17A H17B 109.5 . . ?
C12A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1A C10A 1.870(3) . ?
P1A C12A 1.882(3) . ?
P1A C11A 1.878(3) . ?
P1 C10 1.869(2) . ?
P1 C12 1.881(3) . ?
P1 C11 1.888(3) . ?
Cl3 C24 1.766(3) . ?
Cl1 C24 1.751(4) . ?
Cl2 C24 1.753(3) . ?
N1 C2 1.322(3) . ?
N1 C9 1.368(3) . ?
N2 C8 1.323(3) . ?
N2 C9 1.366(3) . ?
N2A C8A 1.330(4) . ?
N2A C9A 1.368(4) . ?
N1A C9A 1.369(4) . ?
N1A C2A 1.317(4) . ?
N3 C19 1.337(4) . ?
N3 C23 1.336(4) . ?
N3A C19A 1.341(4) . ?
N3A C23A 1.333(5) . ?
C8 C19 1.500(4) . ?
C8 C7 1.415(4) . ?
C2 C10 1.506(3) . ?
C2 C3 1.424(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.415(4) . ?
C6 C7 1.360(4) . ?
C9 C5 1.419(4) . ?
C8A C19A 1.491(4) . ?
C8A C7A 1.414(4) . ?
C19A C20A 1.391(4) . ?
C5A C9A 1.413(4) . ?
C5A C6A 1.416(4) . ?
C5A C4A 1.409(4) . ?
C5 C4 1.414(4) . ?
C19 C20 1.384(5) . ?
C2A C10A 1.507(4) . ?
C2A C3A 1.428(4) . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.360(4) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.366(4) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.385(4) . ?
C3 H3 0.9300 . ?
C12 C17 1.534(5) . ?
C12 C18 1.541(4) . ?
C12 C16 1.534(4) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C3A H3A 0.9300 . ?
C3A C4A 1.361(4) . ?
C12A C18A 1.537(5) . ?
C12A C16A 1.556(5) . ?
C12A C17A 1.525(5) . ?
C11A C14A 1.532(4) . ?
C11A C13A 1.542(4) . ?
C11A C15A 1.531(5) . ?
C11 C14 1.535(4) . ?
C11 C13 1.540(4) . ?
C11 C15 1.531(5) . ?
C7A H7A 0.9300 . ?
C4A H4A 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.395(4) . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C15 H15D 0.9600 . ?
C15 H15E 0.9600 . ?
C15 H15F 0.9600 . ?
C21A H21A 0.9300 . ?
C21A C22A 1.383(5) . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.369(6) . ?
C22 C21 1.385(5) . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C23 H23 0.9300 . ?
C22A H22A 0.9300 . ?
C22A C23A 1.380(6) . ?
C21 H21 0.9300 . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C24 H24 0.9800 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C23A H23A 0.9300 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
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
_geom_torsion_publ_flag
N1 C2 C10 P1 137.1(2) . . . . ?
N1 C2 C3 C4 -0.5(4) . . . . ?
N1 C9 C5 C6 -179.2(2) . . . . ?
N1 C9 C5 C4 -0.7(4) . . . . ?
N2 C8 C19 N3 174.7(3) . . . . ?
N2 C8 C19 C20 -5.6(4) . . . . ?
N2 C8 C7 C6 0.3(4) . . . . ?
N2 C9 C5 C6 -0.3(4) . . . . ?
N2 C9 C5 C4 178.2(2) . . . . ?
N2A C8A C19A N3A -165.6(2) . . . . ?
N2A C8A C19A C20A 13.9(4) . . . . ?
N2A C8A C7A C6A -0.7(4) . . . . ?
N1A C2A C10A P1A -132.5(2) . . . . ?
N1A C2A C3A C4A 0.6(4) . . . . ?
N3 C19 C20 C21 0.6(5) . . . . ?
N3A C19A C20A C21A 2.1(4) . . . . ?
C8 N2 C9 N1 177.7(2) . . . . ?
C8 N2 C9 C5 -1.3(4) . . . . ?
C8 C19 C20 C21 -179.1(3) . . . . ?
C2 N1 C9 N2 -177.1(2) . . . . ?
C2 N1 C9 C5 1.9(4) . . . . ?
C6 C5 C4 C3 177.4(3) . . . . ?
C9 N1 C2 C10 175.7(2) . . . . ?
C9 N1 C2 C3 -1.3(4) . . . . ?
C9 N2 C8 C19 -178.7(2) . . . . ?
C9 N2 C8 C7 1.4(4) . . . . ?
C9 C5 C4 C3 -1.1(4) . . . . ?
C8A N2A C9A N1A -177.5(2) . . . . ?
C8A N2A C9A C5A 1.8(4) . . . . ?
C8A C19A C20A C21A -177.4(3) . . . . ?
C19A N3A C23A C22A -0.2(5) . . . . ?
C19A C8A C7A C6A -179.9(2) . . . . ?
C19A C20A C21A C22A -1.2(4) . . . . ?
C5A C6A C7A C8A 2.4(4) . . . . ?
C5 C6 C7 C8 -1.9(4) . . . . ?
C5 C4 C3 C2 1.6(4) . . . . ?
C19 N3 C23 C22 0.5(5) . . . . ?
C19 C8 C7 C6 -179.7(2) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C9A N2A C8A C19A 177.8(2) . . . . ?
C9A N2A C8A C7A -1.4(4) . . . . ?
C9A N1A C2A C10A -177.3(2) . . . . ?
C9A N1A C2A C3A 1.3(4) . . . . ?
C9A C5A C6A C7A -2.0(4) . . . . ?
C9A C5A C4A C3A 1.3(4) . . . . ?
C2A N1A C9A N2A 177.4(2) . . . . ?
C2A N1A C9A C5A -1.9(4) . . . . ?
C2A C3A C4A C5A -1.9(4) . . . . ?
C10 P1 C12 C17 -63.4(2) . . . . ?
C10 P1 C12 C18 58.0(2) . . . . ?
C10 P1 C12 C16 172.2(2) . . . . ?
C10 P1 C11 C14 165.2(2) . . . . ?
C10 P1 C11 C13 -79.5(2) . . . . ?
C10 P1 C11 C15 41.4(3) . . . . ?
C10 C2 C3 C4 -177.4(3) . . . . ?
C7 C8 C19 N3 -5.3(4) . . . . ?
C7 C8 C19 C20 174.4(3) . . . . ?
C7 C6 C5 C9 2.0(4) . . . . ?
C7 C6 C5 C4 -176.5(3) . . . . ?
C6A C5A C9A N2A -0.1(4) . . . . ?
C6A C5A C9A N1A 179.1(2) . . . . ?
C6A C5A C4A C3A -177.1(2) . . . . ?
C20A C21A C22A C23A -0.3(5) . . . . ?
C3 C2 C10 P1 -45.8(3) . . . . ?
C12 P1 C10 C2 -96.2(2) . . . . ?
C12 P1 C11 C14 57.7(3) . . . . ?
C12 P1 C11 C13 172.94(19) . . . . ?
C12 P1 C11 C15 -66.1(3) . . . . ?
C10A P1A C12A C18A -63.3(3) . . . . ?
C10A P1A C12A C16A -176.3(3) . . . . ?
C10A P1A C12A C17A 61.0(3) . . . . ?
C10A P1A C11A C14A -174.5(3) . . . . ?
C10A P1A C11A C13A 71.4(2) . . . . ?
C10A P1A C11A C15A -48.5(3) . . . . ?
C10A C2A C3A C4A 179.2(3) . . . . ?
C3A C2A C10A P1A 48.8(3) . . . . ?
C12A P1A C10A C2A 93.9(2) . . . . ?
C12A P1A C11A C14A -67.0(3) . . . . ?
C12A P1A C11A C13A 178.8(2) . . . . ?
C12A P1A C11A C15A 58.9(3) . . . . ?
C11A P1A C10A C2A -151.1(2) . . . . ?
C11A P1A C12A C18A -170.3(2) . . . . ?
C11A P1A C12A C16A 76.7(3) . . . . ?
C11A P1A C12A C17A -45.9(4) . . . . ?
C11 P1 C10 C2 149.1(2) . . . . ?
C11 P1 C12 C17 43.1(2) . . . . ?
C11 P1 C12 C18 164.4(2) . . . . ?
C11 P1 C12 C16 -81.3(2) . . . . ?
C7A C8A C19A N3A 13.6(4) . . . . ?
C7A C8A C19A C20A -166.9(2) . . . . ?
C4A C5A C9A N2A -178.6(2) . . . . ?
C4A C5A C9A N1A 0.6(4) . . . . ?
C4A C5A C6A C7A 176.4(2) . . . . ?
C21A C22A C23A N3A 1.0(5) . . . . ?
C23 N3 C19 C8 178.7(3) . . . . ?
C23 N3 C19 C20 -1.0(5) . . . . ?
C23 C22 C21 C20 -0.8(5) . . . . ?
C21 C22 C23 N3 0.4(6) . . . . ?
C23A N3A C19A C8A 178.1(3) . . . . ?
C23A N3A C19A C20A -1.4(4) . . . . ?
