#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:01:14 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/06/1570627.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_1570627
loop_
_publ_author_name
'Kato, Yugo'
'Nishimura, Kazutoshi'
'Nishii, Yuji'
'Hirano, Koji'
_publ_section_title
;
 Direct synthesis of spirobifluorenes by formal dehydrative coupling of
 biaryls and fluorenones.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2112
_journal_page_last               2117
_journal_paper_doi               10.1039/d3sc05977d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C2 H4 Cl2, C56 H41 N'
_chemical_formula_sum            'C58 H45 Cl2 N'
_chemical_formula_weight         826.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-02 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.9290(10)
_cell_angle_beta                 102.9010(10)
_cell_angle_gamma                107.0460(10)
_cell_formula_units_Z            2
_cell_length_a                   10.38100(10)
_cell_length_b                   14.3480(2)
_cell_length_c                   15.61030(10)
_cell_measurement_reflns_used    17419
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      74.1000
_cell_measurement_theta_min      4.0130
_cell_volume                     2138.07(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  64.00   0.50    0.27    --   42.80 -57.00  60.00  186
  2  ω     56.00  84.00   0.50    0.27    --   42.80-130.00 -24.00   56
  3  ω     42.00  67.00   0.50    1.08    --   76.50-130.00 -24.00   50
  4  ω     54.00  89.00   0.50    0.27    --   42.80-140.00 161.00   70
  5  ω     49.00  74.00   0.50    1.08    --   76.50-140.00 161.00   50
  6  ω    116.00 151.00   0.50    1.08    --   76.50  77.00   0.00   70
  7  ω     85.00 110.00   0.50    1.08    --   76.50 130.00  47.00   50
  8  ω     68.00  93.00   0.50    0.27    --   42.80 130.00  47.00   50
  9  ω     54.00 111.00   0.50    1.08    --   76.50  77.00   0.00  114
 10  ω     71.00 102.00   0.50    0.27    --   42.80 125.00 -60.00   62
 11  ω     62.00 113.00   0.50    0.27    --   42.80 140.00-138.00  102
 12  ω     82.00 107.00   0.50    1.08    --   76.50 140.00-138.00   50
 13  ω    -61.00 -34.00   0.50    1.08    -- -106.00 125.00 -90.00   54
 14  ω    -63.00 -37.00   0.50    1.08    -- -106.00 125.00-150.00   52
 15  ω    -77.00 -35.00   0.50    1.08    -- -106.00  77.00 -90.00   84
 16  ω   -104.00 -21.00   0.50    0.27    --  -42.80 140.00-138.00  166
 17  ω    -86.00 -58.00   0.50    0.27    --  -42.80 130.00  47.00   56
 18  ω   -111.00 -40.00   0.50    1.08    -- -106.00 130.00  47.00  142
 19  ω    -67.00 -32.00   0.50    1.08    -- -106.00 125.00  90.00   70
 20  ω    -57.00 -32.00   0.50    1.08    -- -106.00  77.00  90.00   50
 21  ω    -86.00 -40.00   0.50    1.08    -- -106.00 125.00  30.00   92
 22  ω   -103.00 -77.00   0.50    1.08    -- -106.00 125.00 -90.00   52
 23  ω   -104.00 -78.00   0.50    1.08    -- -106.00 140.00-138.00   52
 24  ω   -115.00 -33.00   0.50    1.08    -- -106.00 125.00 -60.00  164
 25  ω   -101.00 -76.00   0.50    1.08    -- -106.00 125.00 -30.00   50
 26  ω   -126.00 -71.00   0.50    1.08    -- -106.00  57.00 -90.00  110
 27  ω   -128.00 -81.00   0.50    1.08    -- -106.00  77.00 -90.00   94
 28  ω   -112.00 -86.00   0.50    1.08    -- -106.00 125.00-150.00   52
 29  ω   -117.00 -82.00   0.50    1.08    -- -106.00 125.00-120.00   70
 30  ω   -128.00 -32.00   0.50    1.08    -- -106.00  57.00 -30.00  192
 31  ω    -99.00 -58.00   0.50    1.08    -- -106.00  57.00  90.00   82
 32  ω   -106.00 -75.00   0.50    1.08    -- -106.00  77.00  90.00   62
 33  ω   -104.00 -31.00   0.50    1.08    -- -106.00  37.00  90.00  146
 34  ω    -94.00 -60.00   0.50    1.08    -- -106.00 125.00 150.00   68
 35  ω   -114.00 -77.00   0.50    1.08    -- -106.00 125.00  90.00   74
 36  ω   -129.00 -35.00   0.50    1.08    -- -106.00 142.00  -4.72  188
 37  ω   -127.00-101.00   0.50    1.08    -- -106.00 139.00 128.10   52
 38  ω   -177.00 -75.00   0.50    1.08    -- -106.00 -19.00-120.00  204
 39  ω   -117.00 -84.00   0.50    1.08    -- -106.00 -37.00-150.00   66
 40  ω   -133.00 -28.00   0.50    1.08    -- -106.00  19.00-150.00  210
 41  ω   -115.00 -15.00   0.50    0.27    --  -42.80 -77.00 -30.00  200
 42  ω    -99.00 -70.00   0.50    1.08    -- -106.00-125.00   0.00   58
 43  ω   -116.00 -88.00   0.50    1.08    -- -106.00-130.00 -24.00   56
 44  ω   -130.00-105.00   0.50    1.08    -- -106.00-125.00   0.00   50
 45  ω   -143.00 -99.00   0.50    1.08    -- -106.00 -77.00  60.00   88
 46  ω   -123.00 -98.00   0.50    1.08    -- -106.00-140.00 161.00   50
 47  ω   -112.00 -87.00   0.50    0.27    --  -42.80-140.00 161.00   50
 48  ω   -115.00 -70.00   0.50    0.27    --  -42.80-125.00  60.00   90
 49  ω   -108.00 -83.00   0.50    0.27    --  -42.80-130.00 -24.00   50
 50  ω   -112.00 -71.00   0.50    1.08    -- -106.00-125.00-150.00   82
 51  ω   -173.00-137.00   0.50    1.08    -- -106.00-125.00   0.00   72
 52  ω   -174.00-115.00   0.50    1.08    -- -106.00-125.00-150.00  118
 53  ω   -177.00 -84.00   0.50    1.08    -- -106.00 -37.00-180.00  186
 54  ω   -166.00-125.00   0.50    1.08    -- -106.00 -37.00-150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684576000
_diffrn_orient_matrix_UB_12      -0.0354427000
_diffrn_orient_matrix_UB_13      -0.1003888000
_diffrn_orient_matrix_UB_21      0.1326946000
_diffrn_orient_matrix_UB_22      0.0649464000
_diffrn_orient_matrix_UB_23      -0.0209309000
_diffrn_orient_matrix_UB_31      0.0596509000
_diffrn_orient_matrix_UB_32      -0.0864867000
_diffrn_orient_matrix_UB_33      0.0034904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33580
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.235
_diffrn_reflns_theta_min         3.265
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       prism
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         8587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0547P)²+0.6346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7638
_reflns_number_total             8587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05977d2.cif
_cod_data_source_block           kato_210302_1
_cod_depositor_comments
'Adding full bibliography for 1570621--1570629.cif.'
_cod_database_code               1570627
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C58 H45 N Cl2'
_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 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,
 H60B), C3(H3A,H3B), C2(H2A,H2B), C2A(H2AA,H2AB), C3A(H3AA,H3AB)
3.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C31(H31), C12(H12), C9(H9), C29(H29), C47(H47), C28(H28), C21(H21),
 C39(H39), C18(H18), C24(H24), C27(H27), C52(H52), C42(H42), C22(H22), C15(H15),
  C23(H23), C26(H26), C50(H50), C48(H48), C41(H41), C17(H17), C40(H40),
 C55(H55), C53(H53), C16(H16), C49(H49), C54(H54)
3.c Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C)
;
_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 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.710
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl4 Cl -0.58816(5) 0.21166(3) -0.03097(3) 0.05017(13) Uani 1 1 d . . . . .
Cl1 Cl -0.34300(6) 0.43102(3) 0.06431(3) 0.05766(14) Uani 1 1 d . . . . .
N36 N 0.61467(11) 0.67938(8) 0.54196(7) 0.0215(2) Uani 1 1 d . . . . .
C11 C 0.45926(12) 0.75687(9) 0.56498(8) 0.0195(2) Uani 1 1 d . . . . .
C19 C 0.41149(13) 1.01744(9) 0.72973(8) 0.0208(2) Uani 1 1 d . . . . .
C35 C 0.50094(12) 0.64698(9) 0.46783(8) 0.0197(2) Uani 1 1 d . . . . .
C43 C -0.11201(13) 0.56570(9) 0.26134(8) 0.0221(2) Uani 1 1 d . . . . .
C25 C 0.31318(12) 0.87356(9) 0.78612(8) 0.0201(2) Uani 1 1 d . . . . .
C20 C 0.21471(13) 0.92316(9) 0.76807(8) 0.0219(2) Uani 1 1 d . . . . .
C32 C 0.25336(12) 0.60876(9) 0.33848(8) 0.0202(2) Uani 1 1 d . . . . .
C46 C 0.16348(13) 0.50551(9) 0.19881(8) 0.0217(2) Uani 1 1 d . . . . .
C34 C 0.47634(13) 0.57901(9) 0.39116(8) 0.0210(2) Uani 1 1 d . . . . .
H34 H 0.540557 0.547562 0.383506 0.025 Uiso 1 1 calc R . . . .
C31 C 0.27713(12) 0.67488(9) 0.41432(8) 0.0205(2) Uani 1 1 d . . . . .
H31 H 0.211977 0.705527 0.421734 0.025 Uiso 1 1 calc R . . . .
C45 C 0.08144(13) 0.65658(9) 0.21746(8) 0.0218(2) Uani 1 1 d . . . . .
C38 C -0.00791(12) 0.52258(9) 0.28853(8) 0.0207(2) Uani 1 1 d . . . . .
C5 C 0.44725(12) 0.92895(9) 0.76263(8) 0.0194(2) Uani 1 1 d . . . . .
C10 C 0.59008(12) 0.74494(9) 0.60266(8) 0.0200(2) Uani 1 1 d . . . . .
C13 C 0.48595(12) 0.86444(9) 0.69670(8) 0.0200(2) Uani 1 1 d . . . . .
C14 C 0.27734(13) 1.01408(9) 0.73502(8) 0.0224(2) Uani 1 1 d . . . . .
C8 C 0.61551(12) 0.85158(9) 0.73483(8) 0.0209(2) Uani 1 1 d . . . . .
C30 C 0.40241(12) 0.69437(9) 0.47975(8) 0.0192(2) Uani 1 1 d . . . . .
C7 C 0.66978(13) 0.90870(9) 0.82568(8) 0.0215(2) Uani 1 1 d . . . . .
C12 C 0.40768(12) 0.81842(9) 0.61245(8) 0.0202(2) Uani 1 1 d . . . . .
H12 H 0.323125 0.827845 0.587737 0.024 Uiso 1 1 calc R . . . .
C44 C -0.05678(13) 0.64887(9) 0.21691(8) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.67026(13) 0.79222(9) 0.68817(8) 0.0221(2) Uani 1 1 d . . . . .
H9 H 0.756003 0.784450 0.712735 0.027 Uiso 1 1 calc R . . . .
C6 C 0.57477(12) 0.95590(9) 0.84163(8) 0.0203(2) Uani 1 1 d . . . . .
C33 C 0.35048(13) 0.56087(9) 0.32681(8) 0.0203(2) Uani 1 1 d . . . . .
C29 C 0.59892(13) 1.01585(9) 0.92182(8) 0.0231(3) Uani 1 1 d . . . . .
H29 H 0.535971 1.047765 0.931215 0.028 Uiso 1 1 calc R . . . .
C37 C 0.12352(13) 0.57465(9) 0.26034(8) 0.0211(2) Uani 1 1 d . . . . .
C51 C 0.29281(13) 0.49559(9) 0.23969(8) 0.0221(2) Uani 1 1 d . . . . .
C47 C 0.08957(14) 0.45641(10) 0.11359(9) 0.0256(3) Uani 1 1 d . . . . .
H47 H 0.005335 0.464807 0.086281 0.031 Uiso 1 1 calc R . . . .
C28 C 0.71980(14) 1.02724(10) 0.98811(9) 0.0264(3) Uani 1 1 d . . . . .
H28 H 0.737976 1.067264 1.042396 0.032 Uiso 1 1 calc R . . . .
C21 C 0.08290(13) 0.88355(10) 0.78248(9) 0.0267(3) Uani 1 1 d . . . . .
H21 H 0.016489 0.915530 0.769870 0.032 Uiso 1 1 calc R . . . .
C39 C -0.02964(14) 0.44501(10) 0.33608(9) 0.0268(3) Uani 1 1 d . . . . .
H39 H 0.040122 0.417031 0.354337 0.032 Uiso 1 1 calc R . . . .
C18 C 0.49456(14) 1.09529(10) 0.69965(9) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.582849 1.096654 0.695011 0.032 Uiso 1 1 calc R . . . .
C24 C 0.28397(14) 0.78607(9) 0.82035(9) 0.0249(3) Uani 1 1 d . . . . .
H24 H 0.350238 0.753976 0.832963 0.030 Uiso 1 1 calc R . . . .
C27 C 0.81341(14) 0.97921(10) 0.97367(9) 0.0271(3) Uani 1 1 d . . . . .
H27 H 0.892836 0.986747 1.018921 0.033 Uiso 1 1 calc R . . . .
C52 C 0.16050(15) 0.73189(10) 0.18266(9) 0.0281(3) Uani 1 1 d . . . . .
H52 H 0.251979 0.736830 0.183047 0.034 Uiso 1 1 calc R . . . .
C56 C 0.73542(13) 0.64457(10) 0.55556(9) 0.0240(3) Uani 1 1 d . . . . .
H56A H 0.702483 0.572945 0.543065 0.029 Uiso 1 1 calc R . . . .
H56B H 0.787031 0.664168 0.617745 0.029 Uiso 1 1 calc R . . . .
C57 C 0.83468(13) 0.68302(10) 0.49835(9) 0.0252(3) Uani 1 1 d . . . . .
H57A H 0.780853 0.667324 0.436590 0.030 Uiso 1 1 calc R . . . .
H57B H 0.901119 0.646957 0.504355 0.030 Uiso 1 1 calc R . . . .
C42 C -0.24089(14) 0.52879(10) 0.28039(9) 0.0272(3) Uani 1 1 d . . . . .
H42 H -0.311142 0.556239 0.261764 0.033 Uiso 1 1 calc R . . . .
C22 C 0.05308(14) 0.79517(11) 0.81612(9) 0.0296(3) Uani 1 1 d . . . . .
H22 H -0.034381 0.767682 0.825860 0.036 Uiso 1 1 calc R . . . .
C15 C 0.22608(15) 1.09065(11) 0.71227(9) 0.0293(3) Uani 1 1 d . . . . .
H15 H 0.137525 1.089196 0.716372 0.035 Uiso 1 1 calc R . . . .
C23 C 0.15266(15) 0.74732(10) 0.83541(9) 0.0291(3) Uani 1 1 d . . . . .
H23 H 0.131226 0.688794 0.858629 0.035 Uiso 1 1 calc R . . . .
C26 C 0.79028(13) 0.91998(10) 0.89261(9) 0.0252(3) Uani 1 1 d . . . . .
H26 H 0.853802 0.888590 0.883245 0.030 Uiso 1 1 calc R . . . .
C50 C 0.34550(14) 0.43205(10) 0.19576(9) 0.0282(3) Uani 1 1 d . . . . .
H50 H 0.429803 0.423605 0.222814 0.034 Uiso 1 1 calc R . . . .
C48 C 0.14352(15) 0.39424(10) 0.06946(9) 0.0302(3) Uani 1 1 d . . . . .
H48 H 0.095166 0.361035 0.012169 0.036 Uiso 1 1 calc R . . . .
C58 C 0.91656(14) 0.79328(10) 0.51841(10) 0.0298(3) Uani 1 1 d . . . . .
H58A H 0.964005 0.812180 0.581340 0.036 Uiso 1 1 calc R . . . .
H58B H 0.852864 0.830850 0.504238 0.036 Uiso 1 1 calc R . . . .
C41 C -0.26247(14) 0.45020(10) 0.32774(10) 0.0296(3) Uani 1 1 d . . . . .
H41 H -0.348115 0.424665 0.340491 0.035 Uiso 1 1 calc R . . . .
C17 C 0.44280(16) 1.17152(11) 0.67648(10) 0.0326(3) Uani 1 1 d . . . . .
H17 H 0.497201 1.224464 0.656259 0.039 Uiso 1 1 calc R . . . .
C40 C -0.15718(15) 0.40946(10) 0.35620(10) 0.0302(3) Uani 1 1 d . . . . .
H40 H -0.172340 0.357979 0.388978 0.036 Uiso 1 1 calc R . . . .
C55 C -0.11647(15) 0.71633(11) 0.18023(10) 0.0306(3) Uani 1 1 d . . . . .
H55 H -0.208286 0.711121 0.179102 0.037 Uiso 1 1 calc R . . . .
C53 C 0.10139(16) 0.80014(11) 0.14709(10) 0.0338(3) Uani 1 1 d . . . . .
H53 H 0.154178 0.851612 0.124431 0.041 Uiso 1 1 calc R . . . .
C59 C 1.02378(15) 0.81684(11) 0.46337(10) 0.0331(3) Uani 1 1 d . . . . .
H59A H 1.088409 0.780539 0.480345 0.040 Uiso 1 1 calc R . . . .
H59B H 0.975012 0.792171 0.401165 0.040 Uiso 1 1 calc R . . . .
C16 C 0.31066(16) 1.16929(11) 0.68328(10) 0.0337(3) Uani 1 1 d . . . . .
H16 H 0.278348 1.221230 0.668200 0.040 Uiso 1 1 calc R . . . .
C49 C 0.26952(15) 0.38159(11) 0.11074(10) 0.0322(3) Uani 1 1 d . . . . .
H49 H 0.303386 0.338814 0.081086 0.039 Uiso 1 1 calc R . . . .
C54 C -0.03617(17) 0.79183(11) 0.14523(10) 0.0348(3) Uani 1 1 d . . . . .
H54 H -0.075023 0.837201 0.120324 0.042 Uiso 1 1 calc R . . . .
C60 C 1.10788(18) 0.92477(12) 0.47166(12) 0.0412(4) Uani 1 1 d . . . . .
H60A H 1.155373 0.950806 0.533845 0.049 Uiso 1 1 calc R . . . .
H60B H 1.044664 0.961397 0.452004 0.049 Uiso 1 1 calc R . . . .
C61 C 1.2150(2) 0.94101(15) 0.41770(14) 0.0531(5) Uani 1 1 d . . . . .
H61A H 1.168729 0.915663 0.355995 0.080 Uiso 1 1 calc GR . . . .
H61B H 1.280347 0.907230 0.438470 0.080 Uiso 1 1 calc GR . . . .
H61C H 1.263770 1.010421 0.424480 0.080 Uiso 1 1 calc GR . . . .
C3 C -0.4510(3) 0.2759(3) -0.0719(2) 0.0467(10) Uani 0.699(8) 1 d . . P A 1
H3A H -0.368047 0.259969 -0.044988 0.056 Uiso 0.699(8) 1 calc R . P A 1
H3B H -0.473997 0.254684 -0.135735 0.056 Uiso 0.699(8) 1 calc R . P A 1
C2 C -0.4207(5) 0.3846(2) -0.05348(19) 0.0529(10) Uani 0.699(8) 1 d . . P A 1
H2A H -0.506563 0.400188 -0.072254 0.063 Uiso 0.699(8) 1 calc R . P A 1
H2B H -0.357390 0.416631 -0.087277 0.063 Uiso 0.699(8) 1 calc R . P A 1
C2A C -0.3489(9) 0.3592(6) -0.0365(4) 0.047(2) Uani 0.301(8) 1 d . . P A 2
H2AA H -0.294718 0.400348 -0.070538 0.057 Uiso 0.301(8) 1 calc R . P A 2
H2AB H -0.310193 0.306574 -0.023247 0.057 Uiso 0.301(8) 1 calc R . P A 2
C3A C -0.4986(9) 0.3166(6) -0.0886(4) 0.046(2) Uani 0.301(8) 1 d . . P A 2
H3AA H -0.504891 0.290982 -0.149472 0.055 Uiso 0.301(8) 1 calc R . P A 2
H3AB H -0.543611 0.367147 -0.089595 0.055 Uiso 0.301(8) 1 calc R . P A 2
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -8 3 0.0293
-1 0 -9 0.0669
-4 8 -2 0.0509
1 0 9 0.0503
6 -6 -1 0.0323
4 5 -4 0.0305
-5 8 1 0.0418
-5 -4 4 0.0278
-6 6 -1 0.0431
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
C35 N36 C10 108.89(10) . . ?
C35 N36 C56 124.83(10) . . ?
C10 N36 C56 126.16(10) . . ?
C10 C11 C30 107.03(10) . . ?
C12 C11 C10 120.52(11) . . ?
C12 C11 C30 132.41(11) . . ?
C14 C19 C5 110.96(11) . . ?
C18 C19 C5 128.09(11) . . ?
C18 C19 C14 120.93(12) . . ?
N36 C35 C34 129.64(11) . . ?
N36 C35 C30 108.73(10) . . ?
C34 C35 C30 121.63(11) . . ?
C38 C43 C44 108.57(11) . . ?
C42 C43 C38 119.97(12) . . ?
C42 C43 C44 131.44(12) . . ?
C20 C25 C5 110.82(11) . . ?
C24 C25 C20 121.26(12) . . ?
C24 C25 C5 127.92(11) . . ?
C25 C20 C14 108.42(11) . . ?
C21 C20 C25 120.20(12) . . ?
C21 C20 C14 131.38(12) . . ?
C31 C32 C33 121.68(11) . . ?
C31 C32 C37 126.79(11) . . ?
C33 C32 C37 111.49(10) . . ?
C51 C46 C37 110.85(11) . . ?
C47 C46 C37 128.15(12) . . ?
C47 C46 C51 121.00(12) . . ?
C35 C34 H34 121.7 . . ?
C33 C34 C35 116.66(11) . . ?
C33 C34 H34 121.7 . . ?
C32 C31 H31 121.1 . . ?
C32 C31 C30 117.87(11) . . ?
C30 C31 H31 121.1 . . ?
C44 C45 C37 110.84(11) . . ?
C52 C45 C44 120.55(12) . . ?
C52 C45 C37 128.61(12) . . ?
C43 C38 C37 110.84(11) . . ?
C39 C38 C43 120.88(12) . . ?
C39 C38 C37 128.27(11) . . ?
C19 C5 C25 101.25(9) . . ?
C13 C5 C19 115.95(10) . . ?
C13 C5 C25 112.21(10) . . ?
C6 C5 C19 114.18(10) . . ?
C6 C5 C25 112.39(10) . . ?
C6 C5 C13 101.36(9) . . ?
N36 C10 C11 108.40(10) . . ?
N36 C10 C9 129.87(11) . . ?
C9 C10 C11 121.70(11) . . ?
C8 C13 C5 110.99(10) . . ?
C12 C13 C5 127.22(11) . . ?
C12 C13 C8 121.71(11) . . ?
C19 C14 C20 108.50(11) . . ?
C15 C14 C19 120.48(12) . . ?
C15 C14 C20 131.00(12) . . ?
C13 C8 C7 107.80(10) . . ?
C9 C8 C13 121.47(11) . . ?
C9 C8 C7 130.73(11) . . ?
C35 C30 C11 106.92(10) . . ?
C31 C30 C11 132.49(11) . . ?
C31 C30 C35 120.58(11) . . ?
C6 C7 C8 108.58(11) . . ?
C26 C7 C8 131.75(12) . . ?
C26 C7 C6 119.66(11) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.83(11) . . ?
C13 C12 H12 121.1 . . ?
C45 C44 C43 108.53(11) . . ?
C55 C44 C43 131.19(12) . . ?
C55 C44 C45 120.25(12) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 C10 116.75(11) . . ?
C8 C9 H9 121.6 . . ?
C7 C6 C5 111.16(10) . . ?
C29 C6 C5 127.24(11) . . ?
C29 C6 C7 121.56(11) . . ?
C32 C33 C51 107.67(11) . . ?
C34 C33 C32 121.57(11) . . ?
C34 C33 C51 130.76(11) . . ?
C6 C29 H29 120.8 . . ?
C6 C29 C28 118.44(12) . . ?
C28 C29 H29 120.8 . . ?
C32 C37 C46 101.03(10) . . ?
C32 C37 C45 115.67(10) . . ?
C32 C37 C38 112.13(10) . . ?
C46 C37 C38 112.93(10) . . ?
C45 C37 C46 114.49(10) . . ?
C45 C37 C38 101.14(9) . . ?
C46 C51 C33 108.78(10) . . ?
C50 C51 C46 119.84(12) . . ?
C50 C51 C33 131.38(12) . . ?
C46 C47 H47 120.5 . . ?
C46 C47 C48 118.93(13) . . ?
C48 C47 H47 120.5 . . ?
C29 C28 H28 119.8 . . ?
C27 C28 C29 120.49(12) . . ?
C27 C28 H28 119.8 . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.54(12) . . ?
C22 C21 H21 120.7 . . ?
C38 C39 H39 120.5 . . ?
C38 C39 C40 119.04(12) . . ?
C40 C39 H39 120.5 . . ?
C19 C18 H18 120.8 . . ?
C19 C18 C17 118.46(13) . . ?
C17 C18 H18 120.8 . . ?
C25 C24 H24 120.9 . . ?
C25 C24 C23 118.30(12) . . ?
C23 C24 H24 120.8 . . ?
C28 C27 H27 119.4 . . ?
C28 C27 C26 121.15(12) . . ?
C26 C27 H27 119.4 . . ?
C45 C52 H52 120.4 . . ?
C45 C52 C53 119.19(13) . . ?
C53 C52 H52 120.4 . . ?
N36 C56 H56A 108.6 . . ?
N36 C56 H56B 108.6 . . ?
N36 C56 C57 114.61(10) . . ?
H56A C56 H56B 107.6 . . ?
C57 C56 H56A 108.6 . . ?
C57 C56 H56B 108.6 . . ?
C56 C57 H57A 108.0 . . ?
C56 C57 H57B 108.0 . . ?
C56 C57 C58 117.01(11) . . ?
H57A C57 H57B 107.3 . . ?
C58 C57 H57A 108.0 . . ?
C58 C57 H57B 108.0 . . ?
C43 C42 H42 120.6 . . ?
C41 C42 C43 118.86(12) . . ?
C41 C42 H42 120.6 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.82(12) . . ?
C23 C22 H22 119.6 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.32(13) . . ?
C16 C15 H15 120.8 . . ?
C24 C23 H23 119.6 . . ?
C22 C23 C24 120.86(13) . . ?
C22 C23 H23 119.6 . . ?
C7 C26 H26 120.7 . . ?
C27 C26 C7 118.67(12) . . ?
C27 C26 H26 120.7 . . ?
C51 C50 H50 120.6 . . ?
C49 C50 C51 118.84(13) . . ?
C49 C50 H50 120.6 . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.35(13) . . ?
C49 C48 H48 119.8 . . ?
C57 C58 H58A 109.6 . . ?
C57 C58 H58B 109.6 . . ?
C57 C58 C59 110.11(11) . . ?
H58A C58 H58B 108.2 . . ?
C59 C58 H58A 109.6 . . ?
C59 C58 H58B 109.6 . . ?
C42 C41 H41 119.7 . . ?
C40 C41 C42 120.66(12) . . ?
C40 C41 H41 119.7 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.70(13) . . ?
C16 C17 H17 119.6 . . ?
C39 C40 C41 120.57(13) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C44 C55 H55 120.6 . . ?
C44 C55 C54 118.81(13) . . ?
C54 C55 H55 120.6 . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.40(13) . . ?
C54 C53 H53 119.8 . . ?
C58 C59 H59A 108.2 . . ?
C58 C59 H59B 108.2 . . ?
H59A C59 H59B 107.3 . . ?
C60 C59 C58 116.54(12) . . ?
C60 C59 H59A 108.2 . . ?
C60 C59 H59B 108.2 . . ?
C15 C16 C17 121.07(13) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C50 C49 C48 120.98(13) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C55 C54 H54 119.6 . . ?
C53 C54 C55 120.79(13) . . ?
C53 C54 H54 119.6 . . ?
C59 C60 H60A 109.0 . . ?
C59 C60 H60B 109.0 . . ?
C59 C60 C61 113.03(14) . . ?
H60A C60 H60B 107.8 . . ?
C61 C60 H60A 109.0 . . ?
C61 C60 H60B 109.0 . . ?
C60 C61 H61A 109.5 . . ?
C60 C61 H61B 109.5 . . ?
C60 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
Cl4 C3 H3A 109.1 . . ?
Cl4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 Cl4 112.3(3) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
Cl1 C2 H2A 109.5 . . ?
Cl1 C2 H2B 109.5 . . ?
C3 C2 Cl1 110.6(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
Cl1 C2A H2AA 110.2 . . ?
Cl1 C2A H2AB 110.2 . . ?
H2AA C2A H2AB 108.5 . . ?
C3A C2A Cl1 107.7(7) . . ?
C3A C2A H2AA 110.2 . . ?
C3A C2A H2AB 110.2 . . ?
Cl4 C3A H3AA 110.2 . . ?
Cl4 C3A H3AB 110.2 . . ?
C2A C3A Cl4 107.4(6) . . ?
C2A C3A H3AA 110.2 . . ?
C2A C3A H3AB 110.2 . . ?
H3AA C3A H3AB 108.5 . . ?
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
Cl4 C3 1.739(3) . ?
Cl4 C3A 1.931(7) . ?
Cl1 C2 1.813(3) . ?
Cl1 C2A 1.784(6) . ?
N36 C35 1.3873(16) . ?
N36 C10 1.3942(15) . ?
N36 C56 1.4601(15) . ?
C11 C10 1.4200(16) . ?
C11 C30 1.4341(17) . ?
C11 C12 1.3991(17) . ?
C19 C5 1.5221(16) . ?
C19 C14 1.4005(17) . ?
C19 C18 1.3850(18) . ?
C35 C34 1.4021(17) . ?
C35 C30 1.4191(16) . ?
C43 C38 1.4010(17) . ?
C43 C44 1.4672(18) . ?
C43 C42 1.3958(18) . ?
C25 C20 1.4012(17) . ?
C25 C5 1.5272(16) . ?
C25 C24 1.3848(18) . ?
C20 C14 1.4694(18) . ?
C20 C21 1.3962(18) . ?
C32 C31 1.3790(17) . ?
C32 C33 1.4101(17) . ?
C32 C37 1.5234(17) . ?
C46 C37 1.5278(16) . ?
C46 C51 1.4055(18) . ?
C46 C47 1.3860(18) . ?
C34 H34 0.9300 . ?
C34 C33 1.3977(17) . ?
C31 H31 0.9300 . ?
C31 C30 1.3991(17) . ?
C45 C44 1.4045(18) . ?
C45 C37 1.5253(17) . ?
C45 C52 1.3843(18) . ?
C38 C37 1.5298(17) . ?
C38 C39 1.3820(18) . ?
C5 C13 1.5220(16) . ?
C5 C6 1.5204(16) . ?
C10 C9 1.3971(17) . ?
C13 C8 1.4157(17) . ?
C13 C12 1.3730(17) . ?
C14 C15 1.3935(18) . ?
C8 C7 1.4741(17) . ?
C8 C9 1.3932(17) . ?
C7 C6 1.4021(17) . ?
C7 C26 1.3969(17) . ?
C12 H12 0.9300 . ?
C44 C55 1.3917(18) . ?
C9 H9 0.9300 . ?
C6 C29 1.3849(17) . ?
C33 C51 1.4744(17) . ?
C29 H29 0.9300 . ?
C29 C28 1.3939(18) . ?
C51 C50 1.3975(18) . ?
C47 H47 0.9300 . ?
C47 C48 1.3941(19) . ?
C28 H28 0.9300 . ?
C28 C27 1.391(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(2) . ?
C39 H39 0.9300 . ?
C39 C40 1.3890(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.393(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.3941(19) . ?
C27 H27 0.9300 . ?
C27 C26 1.3932(19) . ?
C52 H52 0.9300 . ?
C52 C53 1.392(2) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C57 1.5251(18) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C57 C58 1.5267(19) . ?
C42 H42 0.9300 . ?
C42 C41 1.392(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.394(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C23 H23 0.9300 . ?
C26 H26 0.9300 . ?
C50 H50 0.9300 . ?
C50 C49 1.393(2) . ?
C48 H48 0.9300 . ?
C48 C49 1.394(2) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
C58 C59 1.5323(19) . ?
C41 H41 0.9300 . ?
C41 C40 1.391(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.391(2) . ?
C40 H40 0.9300 . ?
C55 H55 0.9300 . ?
C55 C54 1.394(2) . ?
C53 H53 0.9300 . ?
C53 C54 1.391(2) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C59 C60 1.516(2) . ?
C16 H16 0.9300 . ?
C49 H49 0.9300 . ?
C54 H54 0.9300 . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C60 C61 1.517(2) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.487(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.498(13) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
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
4.2013 -7.9799 3.0142 -0.3074 -0.0239 0.9513
-0.9041 0.0577 -9.2927 0.9927 0.0783 -0.0914
-4.2739 8.3673 -1.7666 0.1734 0.0133 -0.9848
1.0189 -0.2958 9.2699 -0.9899 -0.0780 0.1187
6.0048 -6.4695 -1.4822 -0.0330 0.4077 0.9125
3.9726 5.4873 -3.8903 -0.0759 0.9650 -0.2512
-5.3318 7.6049 0.7618 0.0190 -0.2295 -0.9731
-4.8712 -4.0712 3.9787 0.0784 -0.9941 0.0754
-5.7562 6.4672 -1.0904 0.2743 -0.3210 -0.9065
