#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:01:14 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/06/1570622.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_1570622
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         'C38 H39 N'
_chemical_formula_sum            'C38 H39 N'
_chemical_formula_weight         509.70
_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             2021-01-14
_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                116.431(3)
_cell_angle_beta                 95.048(2)
_cell_angle_gamma                94.470(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9754(2)
_cell_length_b                   12.1150(4)
_cell_length_c                   12.3347(3)
_cell_measurement_reflns_used    8423
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      74.0890
_cell_measurement_theta_min      4.0260
_cell_volume                     1450.31(8)
_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      223(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 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00 121.00   0.50    0.73    --   42.80  35.00 -20.00  156
  2  ω    101.00 127.00   0.50    2.92    --   76.50  35.00 -20.00   52
  3  ω     70.00  96.00   0.50    2.92    --   76.50  35.00 -20.00   52
  4  ω     98.00 124.00   0.50    2.92    --   76.50 125.00-150.00   52
  5  ω     85.00 117.00   0.50    0.73    --   42.80 125.00-180.00   64
  6  ω     25.00  50.00   0.50    2.92    --   76.50 -35.00-177.00   50
  7  ω    -32.00  59.00   0.50    0.73    --   42.80 -35.00-177.00  182
  8  ω    -15.00  21.00   0.50    0.73    --  -42.80  35.00 -20.00   72
  9  ω    -62.00 -28.00   0.50    2.92    -- -106.00  35.00 -20.00   68
 10  ω    -77.00 -51.00   0.50    2.92    -- -106.00  57.00 -90.00   52
 11  ω    -98.00 -69.00   0.50    2.92    -- -106.00  37.00-180.00   58
 12  ω    -74.00 -33.00   0.50    2.92    -- -106.00  57.00-180.00   82
 13  ω    -67.00 -41.00   0.50    2.92    -- -106.00 125.00 -90.00   52
 14  ω    -69.00 -34.00   0.50    2.92    -- -106.00 125.00 -30.00   70
 15  ω    -59.00 -32.00   0.50    2.92    -- -106.00 125.00  60.00   54
 16  ω    -96.00 -59.00   0.50    0.73    --  -42.80 125.00 150.00   74
 17  ω   -127.00 -68.00   0.50    2.92    -- -106.00  57.00  90.00  118
 18  ω    -84.00 -29.00   0.50    2.92    -- -106.00  19.00 120.00  110
 19  ω   -111.00 -32.00   0.50    2.92    -- -106.00 125.00 150.00  158
 20  ω   -114.00 -35.00   0.50    2.92    -- -106.00 125.00  30.00  158
 21  ω   -117.00 -75.00   0.50    2.92    -- -106.00 125.00 -90.00   84
 22  ω   -115.00 -63.00   0.50    2.92    -- -106.00 125.00-120.00  104
 23  ω   -105.00 -50.00   0.50    2.92    -- -106.00  77.00 -90.00  110
 24  ω   -119.00 -93.00   0.50    2.92    -- -106.00  35.00 -20.00   52
 25  ω   -113.00 -32.00   0.50    2.92    -- -106.00  77.00  30.00  162
 26  ω   -108.00 -83.00   0.50    2.92    -- -106.00 125.00  90.00   50
 27  ω   -108.00 -65.00   0.50    2.92    -- -106.00 125.00  60.00   86
 28  ω   -117.00 -61.00   0.50    2.92    -- -106.00 125.00   0.00  112
 29  ω   -118.00 -81.00   0.50    2.92    -- -106.00  57.00 -90.00   74
 30  ω   -114.00 -35.00   0.50    2.92    -- -106.00 125.00-180.00  158
 31  ω   -113.00 -88.00   0.50    2.92    -- -106.00  57.00-180.00   50
 32  ω   -120.00 -63.00   0.50    0.73    --  -42.80 -35.00-177.00  114
 33  ω      2.00 102.00   0.50    2.92    --   76.50 -77.00  30.00  200
 34  ω    -44.00 -19.00   0.50    0.73    --  -42.80 -35.00-177.00   50
 35  ω   -115.00 -71.00   0.50    0.73    --  -42.80-125.00-180.00   88
 36  ω   -152.00 -95.00   0.50    2.92    -- -106.00 -35.00-177.00  114
 37  ω   -155.00-130.00   0.50    2.92    -- -106.00 -37.00-120.00   50
 38  ω   -177.00 -75.00   0.50    2.92    -- -106.00 -19.00-120.00  204
 39  ω   -136.00 -83.00   0.50    2.92    -- -106.00-125.00  30.00  106
 40  ω   -101.00 -75.00   0.50    0.73    --  -42.80-125.00 120.00   52
 41  ω   -171.00-144.00   0.50    2.92    -- -106.00-125.00  30.00   54
 42  ω   -174.00 -85.00   0.50    2.92    -- -106.00 -99.00   0.00  178
 43  ω   -172.00-112.00   0.50    2.92    -- -106.00 -37.00 120.00  120
 44  ω   -134.00-109.00   0.50    2.92    -- -106.00  19.00 120.00   50
 45  ω   -176.00-149.00   0.50    2.92    -- -106.00 -99.00 150.00   54
 46  ω   -177.00-111.00   0.50    2.92    -- -106.00 -57.00-150.00  132
;
_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      0.1384506000
_diffrn_orient_matrix_UB_12      -0.0055991000
_diffrn_orient_matrix_UB_13      -0.0105080000
_diffrn_orient_matrix_UB_21      -0.0239376000
_diffrn_orient_matrix_UB_22      -0.1431321000
_diffrn_orient_matrix_UB_23      -0.0628264000
_diffrn_orient_matrix_UB_31      -0.0215111000
_diffrn_orient_matrix_UB_32      -0.0010266000
_diffrn_orient_matrix_UB_33      -0.1255808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20471
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.274
_diffrn_reflns_theta_min         4.041
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63235
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         5815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0723
_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)+(0.1129P)²+0.4895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4776
_reflns_number_total             5815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05977d2.cif
_cod_data_source_block           210114_1
_cod_depositor_comments
'Adding full bibliography for 1570621--1570629.cif.'
_cod_original_cell_volume        1450.31(7)
_cod_database_code               1570622
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C56 H34 N2'
_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 99.77
_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
 Fixed Sof: C21(0.5) H21A(0.5) H21B(0.5) C29(0.5) H29A(0.5) H29B(0.5)
 C9AA(0.5) H9AA(0.5) H9AB(0.5) C5AA(0.5) H5AA(0.5) H5AB(0.5) C2AA(0.5)
 H2AA(0.5) H2AB(0.5) C4AA(0.5) H4AA(0.5) H4AB(0.5) C1AA(0.5) H1AA(0.5)
 H1AB(0.5) C7AA(0.5) H7AA(0.5) H7AB(0.5) C6AA(0.5) H6AA(0.5) H6AB(0.5)
 C8AA(0.5) H8AA(0.5) H8AB(0.5) C0BA(0.5) H0BA(0.5) H0BB(0.5) C2BA(0.5)
 H2BA(0.5) H2BB(0.5) H2BC(0.5) C4BA(0.5) H4BA(0.5) H4BB(0.5) C7BA(0.5)
 H7BA(0.5) H7BB(0.5) C6BA(0.5) H6BA(0.5) H6BB(0.5) C8BA(0.5) H8BA(0.5)
 H8BB(0.5) H8BC(0.5) C5BA(0.5) H5BA(0.5) H5BB(0.5) C1CA(0.5) H1CA(0.5)
 H1CB(0.5) C0CA(0.5) H0CA(0.5) H0CB(0.5) C9BA(0.5) H9BA(0.5) H9BB(0.5)
 C2CA(0.5) H2CA(0.5) H2CB(0.5) C3CA(0.5) H3CA(0.5) H3CB(0.5) C4CA(0.5)
 H4CA(0.5) H4CB(0.5) C5CA(0.5) H5CA(0.5) H5CB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C29(H29A,H29B), C9AA(H9AA,H9AB), C5AA(H5AA,H5AB), C2AA(H2AA,
 H2AB), C4AA(H4AA,H4AB), C1AA(H1AA,H1AB), C7AA(H7AA,H7AB), C6AA(H6AA,H6AB),
 C8AA(H8AA,H8AB), C0BA(H0BA,H0BB), C4BA(H4BA,H4BB), C7BA(H7BA,H7BB), C6BA(H6BA,
 H6BB), C5BA(H5BA,H5BB), C1CA(H1CA,H1CB), C0CA(H0CA,H0CB), C9BA(H9BA,H9BB),
 C2CA(H2CA,H2CB), C3CA(H3CA,H3CB), C4CA(H4CA,H4CB), C5CA(H5CA,H5CB)
3.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C25(H25), C5(H5), C28(H28), C8(H8), C26(H26), C27(H27),
 C7(H7), C6(H6), C0AA(H0AA), C3AA(H3AA), C3BA(H3BA), C1BA(H1BA)
3.c Idealised Me refined as rotating group:
 C2BA(H2BA,H2BB,H2BC), C8BA(H8BA,H8BB,H8BC)
;
_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 1.735
_oxdiff_exptl_absorpt_empirical_full_min 0.538
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
N18 N 1.00008(15) 0.3709(2) 0.34635(16) 0.0660(6) Uani 1 1 d . . . . .
C13 C 1.08402(14) 0.47941(17) 0.12652(15) 0.0409(4) Uani 1 1 d . . . . .
C23 C 0.84054(14) 0.44911(19) 0.01942(16) 0.0446(4) Uani 1 1 d . . . . .
H23 H 0.759448 0.438979 -0.016013 0.054 Uiso 1 1 calc R . . . .
C2 C 1.30387(15) 0.41277(18) 0.12793(15) 0.0420(4) Uani 1 1 d . . . . .
C1 C 1.20882(14) 0.48933(18) 0.20105(15) 0.0423(4) Uani 1 1 d . . . . .
C22 C 1.06283(14) 0.50792(17) 0.02771(14) 0.0393(4) Uani 1 1 d . . . . .
C4 C 1.40188(15) 0.61640(19) 0.23385(16) 0.0455(4) Uani 1 1 d . . . . .
C9 C 1.28140(16) 0.61934(19) 0.26400(15) 0.0453(4) Uani 1 1 d . . . . .
C3 C 1.41604(15) 0.48826(19) 0.15159(16) 0.0440(4) Uani 1 1 d . . . . .
C12 C 0.98636(15) 0.43721(19) 0.16929(16) 0.0455(4) Uani 1 1 d . . . . .
C24 C 0.86333(15) 0.4224(2) 0.11469(16) 0.0481(5) Uani 1 1 d . . . . .
H24 H 0.798473 0.394657 0.143858 0.058 Uiso 1 1 calc R . . . .
C10 C 1.16510(16) 0.4437(2) 0.28904(16) 0.0500(5) Uani 1 1 d . . . . .
C11 C 1.04017(16) 0.4154(2) 0.26890(17) 0.0520(5) Uani 1 1 d . . . . .
C25 C 1.51782(17) 0.4370(2) 0.09915(19) 0.0556(5) Uani 1 1 d . . . . .
H25 H 1.592537 0.486859 0.115104 0.067 Uiso 1 1 calc R . . . .
C5 C 1.4841(2) 0.7261(2) 0.2807(2) 0.0611(6) Uani 1 1 d . . . . .
H5 H 1.563809 0.724932 0.260528 0.073 Uiso 1 1 calc R . . . .
C28 C 1.29270(19) 0.2874(2) 0.05284(19) 0.0566(5) Uani 1 1 d . . . . .
H28 H 1.218403 0.237094 0.037409 0.068 Uiso 1 1 calc R . . . .
C8 C 1.2437(2) 0.7301(2) 0.34145(19) 0.0649(6) Uani 1 1 d . . . . .
H8 H 1.164217 0.732257 0.362406 0.078 Uiso 1 1 calc R . . . .
C26 C 1.5064(2) 0.3117(3) 0.0235(2) 0.0661(6) Uani 1 1 d . . . . .
H26 H 1.573797 0.276444 -0.012422 0.079 Uiso 1 1 calc R . . . .
C14 C 1.21124(18) 0.4174(3) 0.38488(19) 0.0620(6) Uani 1 1 d . . . . .
C27 C 1.3954(2) 0.2369(2) 0.0000(2) 0.0692(6) Uani 1 1 d . . . . .
H27 H 1.389206 0.152120 -0.051625 0.083 Uiso 1 1 calc R . . . .
C7 C 1.3269(3) 0.8390(3) 0.3879(2) 0.0822(8) Uani 1 1 d . . . . .
H7 H 1.302427 0.914336 0.439962 0.099 Uiso 1 1 calc R . . . .
C6 C 1.4447(3) 0.8361(2) 0.3576(2) 0.0773(7) Uani 1 1 d . . . . .
H6 H 1.498607 0.909697 0.389459 0.093 Uiso 1 1 calc R . . . .
C19 C 1.10483(19) 0.3712(3) 0.4189(2) 0.0742(8) Uani 1 1 d . . . . .
C21 C 0.8750(6) 0.3127(6) 0.3434(6) 0.0481(14) Uani 0.5 1 d . . P A 1
H21A H 0.817442 0.369753 0.344082 0.058 Uiso 0.5 1 calc R . P A 1
H21B H 0.873886 0.306481 0.419052 0.058 Uiso 0.5 1 calc R . P A 1
C29 C 0.4056(9) 0.0665(10) 0.2053(8) 0.088(2) Uani 0.5 1 d . . P A 1
H29A H 0.447316 -0.006905 0.172629 0.105 Uiso 0.5 1 calc R . P A 1
H29B H 0.408053 0.101003 0.147960 0.105 Uiso 0.5 1 calc R . P A 1
C9AA C 0.2412(9) 0.0090(9) 0.1941(9) 0.091(2) Uani 0.5 1 d . . P A 1
H9AA H 0.229059 0.027767 0.277225 0.110 Uiso 0.5 1 calc R . P A 1
H9AB H 0.195473 0.064294 0.174120 0.110 Uiso 0.5 1 calc R . P A 1
C5AA C 0.8249(6) 0.1863(6) 0.2397(7) 0.0778(18) Uani 0.5 1 d . . P A 1
H5AA H 0.853530 0.121728 0.257763 0.093 Uiso 0.5 1 calc R . P A 1
H5AB H 0.854349 0.177923 0.164898 0.093 Uiso 0.5 1 calc R . P A 1
C2AA C 0.5884(5) 0.1274(6) 0.2326(5) 0.0803(15) Uani 0.5 1 d . . P A 2
H2AA H 0.619013 0.064034 0.251449 0.096 Uiso 0.5 1 calc R . P A 2
H2AB H 0.596199 0.104395 0.147747 0.096 Uiso 0.5 1 calc R . P A 2
C4AA C 0.6635(5) 0.2453(5) 0.3093(5) 0.0705(12) Uani 0.5 1 d . . P A 2
H4AA H 0.657002 0.267448 0.394282 0.085 Uiso 0.5 1 calc R . P A 2
H4AB H 0.631717 0.309003 0.291748 0.085 Uiso 0.5 1 calc R . P A 2
C1AA C 0.4534(7) 0.1307(11) 0.2493(7) 0.100(3) Uani 0.5 1 d . . P A 2
H1AA H 0.424037 0.196692 0.234163 0.120 Uiso 0.5 1 calc R . P A 2
H1AB H 0.445533 0.150358 0.333506 0.120 Uiso 0.5 1 calc R . P A 2
C7AA C 0.0132(7) -0.0820(8) 0.2653(7) 0.100(2) Uani 0.5 1 d . . P A 1
H7AA H 0.066475 -0.118755 0.303525 0.119 Uiso 0.5 1 calc R . P A 1
H7AB H 0.033074 0.007572 0.311251 0.119 Uiso 0.5 1 calc R . P A 1
C6AA C 0.0425(8) -0.1232(9) 0.1313(7) 0.106(2) Uani 0.5 1 d . . P A 1
H6AA H 0.006035 -0.208864 0.080916 0.127 Uiso 0.5 1 calc R . P A 1
H6AB H 0.003137 -0.072678 0.099459 0.127 Uiso 0.5 1 calc R . P A 1
C8AA C -0.1195(9) -0.1178(8) 0.2746(11) 0.125(4) Uani 0.5 1 d . . P A 1
H8AA H -0.173129 -0.085184 0.232214 0.151 Uiso 0.5 1 calc R . P A 1
H8AB H -0.137978 -0.207692 0.232809 0.151 Uiso 0.5 1 calc R . P A 1
C0BA C 0.1737(8) -0.1132(7) 0.1197(7) 0.106(2) Uani 0.5 1 d . . P A 1
H0BA H 0.210940 -0.171961 0.141338 0.127 Uiso 0.5 1 calc R . P A 1
H0BB H 0.182084 -0.137062 0.034762 0.127 Uiso 0.5 1 calc R . P A 1
C2BA C -0.1464(8) -0.0759(7) 0.3919(9) 0.122(3) Uani 0.5 1 d . . P A 1
H2BA H -0.087222 -0.098653 0.437911 0.183 Uiso 0.5 1 calc GR . P A 1
H2BB H -0.227602 -0.112648 0.390438 0.183 Uiso 0.5 1 calc GR . P A 1
H2BC H -0.143056 0.012975 0.429531 0.183 Uiso 0.5 1 calc GR . P A 1
C0AA C 1.3277(2) 0.4293(3) 0.4490(2) 0.0752(8) Uani 1 1 d . . . . .
H0AA H 1.398402 0.458776 0.428514 0.090 Uiso 1 1 calc R . . . .
C3AA C 1.3356(2) 0.3967(4) 0.5426(3) 0.1021(12) Uani 1 1 d . . . . .
H3AA H 1.412479 0.404701 0.585596 0.123 Uiso 1 1 calc R . . . .
C3BA C 1.1142(2) 0.3374(4) 0.5129(3) 0.1030(12) Uani 1 1 d . . . . .
H3BA H 1.044830 0.306161 0.533698 0.124 Uiso 1 1 calc R . . . .
C1BA C 1.2305(3) 0.3518(4) 0.5743(3) 0.1159(14) Uani 1 1 d . . . . .
H1BA H 1.238991 0.330995 0.638436 0.139 Uiso 1 1 calc R . . . .
C4BA C 0.1870(8) -0.0137(10) 0.1059(8) 0.120(3) Uani 0.5 1 d . . P A 2
H4BA H 0.203627 -0.097124 0.087944 0.144 Uiso 0.5 1 calc R . P A 2
H4BB H 0.211518 0.001926 0.039785 0.144 Uiso 0.5 1 calc R . P A 2
C7BA C -0.0017(8) -0.1547(9) 0.1864(10) 0.106(2) Uani 0.5 1 d . . P A 2
H7BA H 0.082510 -0.157385 0.215587 0.127 Uiso 0.5 1 calc R . P A 2
H7BB H -0.020195 -0.217565 0.101871 0.127 Uiso 0.5 1 calc R . P A 2
C6BA C -0.0100(8) -0.0357(8) 0.1916(9) 0.115(2) Uani 0.5 1 d . . P A 2
H6BA H 0.025281 0.027856 0.272580 0.138 Uiso 0.5 1 calc R . P A 2
H6BB H -0.096468 -0.026309 0.179827 0.138 Uiso 0.5 1 calc R . P A 2
C8BA C -0.0862(8) -0.1860(10) 0.2597(9) 0.116(3) Uani 0.5 1 d . . P A 2
H8BA H -0.074399 -0.266026 0.253845 0.173 Uiso 0.5 1 calc GR . P A 2
H8BB H -0.170152 -0.187710 0.228910 0.173 Uiso 0.5 1 calc GR . P A 2
H8BC H -0.068613 -0.124283 0.343707 0.173 Uiso 0.5 1 calc GR . P A 2
C5BA C 0.0526(9) -0.0142(12) 0.1005(10) 0.152(4) Uani 0.5 1 d . . P A 2
H5BA H 0.015283 -0.077530 0.020137 0.183 Uiso 0.5 1 calc R . P A 2
H5BB H 0.034473 0.065225 0.106387 0.183 Uiso 0.5 1 calc R . P A 2
C1CA C 0.6760(6) 0.1708(6) 0.2220(6) 0.0949(19) Uani 0.5 1 d . . P A 1
H1CA H 0.647283 0.244554 0.222161 0.114 Uiso 0.5 1 calc R . P A 1
H1CB H 0.643117 0.099914 0.144542 0.114 Uiso 0.5 1 calc R . P A 1
C0CA C 0.6358(9) 0.1531(8) 0.3186(7) 0.116(3) Uani 0.5 1 d . . P A 1
H0CA H 0.678793 0.217688 0.395669 0.139 Uiso 0.5 1 calc R . P A 1
H0CB H 0.655097 0.073482 0.311337 0.139 Uiso 0.5 1 calc R . P A 1
C9BA C 0.4855(7) 0.1568(9) 0.3172(9) 0.098(2) Uani 0.5 1 d . . P A 1
H9BA H 0.461491 0.143990 0.385040 0.117 Uiso 0.5 1 calc R . P A 1
H9BB H 0.469184 0.239576 0.332150 0.117 Uiso 0.5 1 calc R . P A 1
C2CA C 0.8020(5) 0.2432(7) 0.2905(6) 0.0659(12) Uani 0.5 1 d . . P A 2
H2CA H 0.835778 0.181497 0.309936 0.079 Uiso 0.5 1 calc R . P A 2
H2CB H 0.810071 0.221656 0.205927 0.079 Uiso 0.5 1 calc R . P A 2
C3CA C 0.8701(7) 0.3693(6) 0.3727(7) 0.0519(15) Uani 0.5 1 d . . P A 2
H3CA H 0.831481 0.431873 0.358329 0.062 Uiso 0.5 1 calc R . P A 2
H3CB H 0.868361 0.387665 0.457452 0.062 Uiso 0.5 1 calc R . P A 2
C4CA C 0.2674(9) 0.0708(9) 0.2152(10) 0.094(3) Uani 0.5 1 d . . P A 2
H4CA H 0.248259 0.064352 0.287648 0.113 Uiso 0.5 1 calc R . P A 2
H4CB H 0.273923 0.156524 0.229152 0.113 Uiso 0.5 1 calc R . P A 2
C5CA C 0.3720(11) 0.0090(10) 0.1654(10) 0.101(3) Uani 0.5 1 d . . P A 2
H5CA H 0.371902 -0.015682 0.079035 0.122 Uiso 0.5 1 calc R . P A 2
H5CB H 0.386202 -0.059117 0.184083 0.122 Uiso 0.5 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'
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
-1 -3 8 0.0469
2 3 -8 0.0369
0 6 2 0.0283
0 -7 0 0.0019
0 4 -8 0.0148
0 -4 8 0.0371
5 -1 4 0.1233
-3 3 -7 0.0516
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
C11 N18 C19 106.57(16) . . ?
C11 N18 C21 128.6(3) . . ?
C11 N18 C3CA 122.6(3) . . ?
C19 N18 C21 124.1(3) . . ?
C19 N18 C3CA 127.4(3) . . ?
C22 C13 C1 127.93(14) . . ?
C12 C13 C1 111.11(14) . . ?
C12 C13 C22 120.96(15) . . ?
C22 C23 H23 119.0 2_765 . ?
C24 C23 H23 119.0 . . ?
C24 C23 C22 121.91(15) . 2_765 ?
C3 C2 C1 110.41(16) . . ?
C28 C2 C1 128.88(17) . . ?
C28 C2 C3 120.64(17) . . ?
C2 C1 C13 115.85(14) . . ?
C9 C1 C13 114.42(15) . . ?
C9 C1 C2 101.29(13) . . ?
C10 C1 C13 100.17(13) . . ?
C10 C1 C2 112.00(15) . . ?
C10 C1 C9 113.73(15) . . ?
C13 C22 C23 123.03(14) . 2_765 ?
C13 C22 C22 118.11(18) . 2_765 ?
C23 C22 C22 118.86(18) 2_765 2_765 ?
C9 C4 C3 108.48(16) . . ?
C5 C4 C9 120.2(2) . . ?
C5 C4 C3 131.28(18) . . ?
C4 C9 C1 110.71(16) . . ?
C8 C9 C1 128.92(18) . . ?
C8 C9 C4 120.4(2) . . ?
C2 C3 C4 109.04(15) . . ?
C25 C3 C2 120.38(19) . . ?
C25 C3 C4 130.59(18) . . ?
C13 C12 C24 120.54(16) . . ?
C13 C12 C11 106.68(14) . . ?
C24 C12 C11 132.77(16) . . ?
C23 C24 C12 119.62(15) . . ?
C23 C24 H24 120.2 . . ?
C12 C24 H24 120.2 . . ?
C11 C10 C1 110.75(15) . . ?
C11 C10 C14 108.15(16) . . ?
C14 C10 C1 141.08(16) . . ?
N18 C11 C12 137.61(16) . . ?
C10 C11 N18 111.08(16) . . ?
C10 C11 C12 111.28(16) . . ?
C3 C25 H25 120.5 . . ?
C26 C25 C3 118.9(2) . . ?
C26 C25 H25 120.5 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C2 C28 H28 120.7 . . ?
C2 C28 C27 118.5(2) . . ?
C27 C28 H28 120.7 . . ?
C9 C8 H8 120.6 . . ?
C9 C8 C7 118.8(2) . . ?
C7 C8 H8 120.6 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C10 C14 C19 105.21(16) . . ?
C0AA C14 C10 135.93(19) . . ?
C0AA C14 C19 118.83(18) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 C28 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
N18 C19 C14 108.98(17) . . ?
C3BA C19 N18 129.4(2) . . ?
C3BA C19 C14 121.6(2) . . ?
N18 C21 H21A 107.4 . . ?
N18 C21 H21B 107.4 . . ?
N18 C21 C5AA 119.5(5) . . ?
H21A C21 H21B 107.0 . . ?
C5AA C21 H21A 107.4 . . ?
C5AA C21 H21B 107.4 . . ?
H29A C29 H29B 106.2 . . ?
C9AA C29 H29A 105.8 . . ?
C9AA C29 H29B 105.8 . . ?
C9BA C29 H29A 105.8 . . ?
C9BA C29 H29B 105.8 . . ?
C9BA C29 C9AA 126.2(7) . . ?
C29 C9AA H9AA 104.8 . . ?
C29 C9AA H9AB 104.8 . . ?
H9AA C9AA H9AB 105.8 . . ?
C0BA C9AA C29 130.0(8) . . ?
C0BA C9AA H9AA 104.8 . . ?
C0BA C9AA H9AB 104.8 . . ?
C21 C5AA H5AA 109.8 . . ?
C21 C5AA H5AB 109.8 . . ?
C21 C5AA C1CA 109.4(5) . . ?
H5AA C5AA H5AB 108.2 . . ?
C1CA C5AA H5AA 109.8 . . ?
C1CA C5AA H5AB 109.8 . . ?
H2AA C2AA H2AB 107.8 . . ?
C4AA C2AA H2AA 109.1 . . ?
C4AA C2AA H2AB 109.1 . . ?
C4AA C2AA C1AA 112.7(6) . . ?
C1AA C2AA H2AA 109.1 . . ?
C1AA C2AA H2AB 109.1 . . ?
C2AA C4AA H4AA 109.0 . . ?
C2AA C4AA H4AB 109.0 . . ?
C2AA C4AA C2CA 112.9(5) . . ?
H4AA C4AA H4AB 107.8 . . ?
C2CA C4AA H4AA 109.0 . . ?
C2CA C4AA H4AB 109.0 . . ?
C2AA C1AA H1AA 108.9 . . ?
C2AA C1AA H1AB 108.9 . . ?
C2AA C1AA C5CA 113.5(9) . . ?
H1AA C1AA H1AB 107.7 . . ?
C5CA C1AA H1AA 108.9 . . ?
C5CA C1AA H1AB 108.9 . . ?
H7AA C7AA H7AB 107.6 . . ?
C6AA C7AA H7AA 108.6 . . ?
C6AA C7AA H7AB 108.6 . . ?
C8AA C7AA H7AA 108.6 . . ?
C8AA C7AA H7AB 108.6 . . ?
C8AA C7AA C6AA 114.7(8) . . ?
C7AA C6AA H6AA 108.6 . . ?
C7AA C6AA H6AB 108.6 . . ?
H6AA C6AA H6AB 107.5 . . ?
C0BA C6AA C7AA 114.8(6) . . ?
C0BA C6AA H6AA 108.6 . . ?
C0BA C6AA H6AB 108.6 . . ?
C7AA C8AA H8AA 108.6 . . ?
C7AA C8AA H8AB 108.6 . . ?
H8AA C8AA H8AB 107.6 . . ?
C2BA C8AA C7AA 114.5(9) . . ?
C2BA C8AA H8AA 108.6 . . ?
C2BA C8AA H8AB 108.6 . . ?
C9AA C0BA C6AA 114.7(7) . . ?
C9AA C0BA H0BA 108.6 . . ?
C9AA C0BA H0BB 108.6 . . ?
C6AA C0BA H0BA 108.6 . . ?
C6AA C0BA H0BB 108.6 . . ?
H0BA C0BA H0BB 107.6 . . ?
C8AA C2BA H2BA 109.5 . . ?
C8AA C2BA H2BB 109.5 . . ?
C8AA C2BA H2BC 109.5 . . ?
H2BA C2BA H2BB 109.5 . . ?
H2BA C2BA H2BC 109.5 . . ?
H2BB C2BA H2BC 109.5 . . ?
C14 C0AA H0AA 120.5 . . ?
C3AA C0AA C14 119.0(2) . . ?
C3AA C0AA H0AA 120.5 . . ?
C0AA C3AA H3AA 119.3 . . ?
C0AA C3AA C1BA 121.3(2) . . ?
C1BA C3AA H3AA 119.3 . . ?
C19 C3BA H3BA 121.2 . . ?
C1BA C3BA C19 117.6(2) . . ?
C1BA C3BA H3BA 121.2 . . ?
C3AA C1BA H1BA 119.2 . . ?
C3BA C1BA C3AA 121.7(2) . . ?
C3BA C1BA H1BA 119.2 . . ?
H4BA C4BA H4BB 106.9 . . ?
C5BA C4BA H4BA 107.2 . . ?
C5BA C4BA H4BB 107.2 . . ?
C4CA C4BA H4BA 107.2 . . ?
C4CA C4BA H4BB 107.2 . . ?
C4CA C4BA C5BA 120.3(9) . . ?
H7BA C7BA H7BB 107.7 . . ?
C6BA C7BA H7BA 108.8 . . ?
C6BA C7BA H7BB 108.8 . . ?
C6BA C7BA C8BA 113.9(9) . . ?
C8BA C7BA H7BA 108.8 . . ?
C8BA C7BA H7BB 108.8 . . ?
C7BA C6BA H6BA 108.7 . . ?
C7BA C6BA H6BB 108.7 . . ?
C7BA C6BA C5BA 114.3(10) . . ?
H6BA C6BA H6BB 107.6 . . ?
C5BA C6BA H6BA 108.7 . . ?
C5BA C6BA H6BB 108.7 . . ?
C7BA C8BA H8BA 109.5 . . ?
C7BA C8BA H8BB 109.5 . . ?
C7BA C8BA H8BC 109.5 . . ?
H8BA C8BA H8BB 109.5 . . ?
H8BA C8BA H8BC 109.5 . . ?
H8BB C8BA H8BC 109.5 . . ?
C4BA C5BA C6BA 118.9(9) . . ?
C4BA C5BA H5BA 107.6 . . ?
C4BA C5BA H5BB 107.6 . . ?
C6BA C5BA H5BA 107.6 . . ?
C6BA C5BA H5BB 107.6 . . ?
H5BA C5BA H5BB 107.0 . . ?
C5AA C1CA H1CA 110.0 . . ?
C5AA C1CA H1CB 110.0 . . ?
H1CA C1CA H1CB 108.4 . . ?
C0CA C1CA C5AA 108.3(7) . . ?
C0CA C1CA H1CA 110.0 . . ?
C0CA C1CA H1CB 110.0 . . ?
C1CA C0CA H0CA 109.5 . . ?
C1CA C0CA H0CB 109.5 . . ?
C1CA C0CA C9BA 110.7(7) . . ?
H0CA C0CA H0CB 108.1 . . ?
C9BA C0CA H0CA 109.5 . . ?
C9BA C0CA H0CB 109.5 . . ?
C29 C9BA C0CA 116.9(7) . . ?
C29 C9BA H9BA 108.1 . . ?
C29 C9BA H9BB 108.1 . . ?
C0CA C9BA H9BA 108.1 . . ?
C0CA C9BA H9BB 108.1 . . ?
H9BA C9BA H9BB 107.3 . . ?
C4AA C2CA H2CA 110.0 . . ?
C4AA C2CA H2CB 110.0 . . ?
H2CA C2CA H2CB 108.4 . . ?
C3CA C2CA C4AA 108.3(5) . . ?
C3CA C2CA H2CA 110.0 . . ?
C3CA C2CA H2CB 110.0 . . ?
N18 C3CA C2CA 108.4(5) . . ?
N18 C3CA H3CA 110.0 . . ?
N18 C3CA H3CB 110.0 . . ?
C2CA C3CA H3CA 110.0 . . ?
C2CA C3CA H3CB 110.0 . . ?
H3CA C3CA H3CB 108.4 . . ?
C4BA C4CA H4CA 113.5 . . ?
C4BA C4CA H4CB 113.5 . . ?
C4BA C4CA C5CA 90.5(9) . . ?
H4CA C4CA H4CB 110.8 . . ?
C5CA C4CA H4CA 113.5 . . ?
C5CA C4CA H4CB 113.5 . . ?
C1AA C5CA H5CA 114.1 . . ?
C1AA C5CA H5CB 114.1 . . ?
C4CA C5CA C1AA 87.3(8) . . ?
C4CA C5CA H5CA 114.1 . . ?
C4CA C5CA H5CB 114.1 . . ?
H5CA C5CA H5CB 111.3 . . ?
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
N18 C11 1.376(2) . ?
N18 C19 1.392(3) . ?
N18 C21 1.484(7) . ?
N18 C3CA 1.491(7) . ?
C13 C1 1.546(2) . ?
C13 C22 1.413(2) . ?
C13 C12 1.394(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.423(2) 2_765 ?
C23 C24 1.359(2) . ?
C2 C1 1.528(2) . ?
C2 C3 1.400(2) . ?
C2 C28 1.370(3) . ?
C1 C9 1.525(3) . ?
C1 C10 1.516(2) . ?
C22 C22 1.443(3) 2_765 ?
C4 C9 1.404(2) . ?
C4 C3 1.458(3) . ?
C4 C5 1.397(3) . ?
C9 C8 1.378(3) . ?
C3 C25 1.389(3) . ?
C12 C24 1.416(2) . ?
C12 C11 1.454(2) . ?
C24 H24 0.9300 . ?
C10 C11 1.360(2) . ?
C10 C14 1.418(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.397(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(4) . ?
C14 C19 1.430(3) . ?
C14 C0AA 1.405(3) . ?
C27 H27 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C19 C3BA 1.390(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C5AA 1.512(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C9AA 1.853(13) . ?
C29 C9BA 1.471(10) . ?
C9AA H9AA 0.9700 . ?
C9AA H9AB 0.9700 . ?
C9AA C0BA 1.443(12) . ?
C5AA H5AA 0.9700 . ?
C5AA H5AB 0.9700 . ?
C5AA C1CA 1.614(9) . ?
C2AA H2AA 0.9700 . ?
C2AA H2AB 0.9700 . ?
C2AA C4AA 1.446(8) . ?
C2AA C1AA 1.515(9) . ?
C4AA H4AA 0.9700 . ?
C4AA H4AB 0.9700 . ?
C4AA C2CA 1.558(7) . ?
C1AA H1AA 0.9700 . ?
C1AA H1AB 0.9700 . ?
C1AA C5CA 1.522(12) . ?
C7AA H7AA 0.9700 . ?
C7AA H7AB 0.9700 . ?
C7AA C6AA 1.571(11) . ?
C7AA C8AA 1.515(13) . ?
C6AA H6AA 0.9700 . ?
C6AA H6AB 0.9700 . ?
C6AA C0BA 1.461(11) . ?
C8AA H8AA 0.9700 . ?
C8AA H8AB 0.9700 . ?
C8AA C2BA 1.373(14) . ?
C0BA H0BA 0.9700 . ?
C0BA H0BB 0.9700 . ?
C2BA H2BA 0.9600 . ?
C2BA H2BB 0.9600 . ?
C2BA H2BC 0.9600 . ?
C0AA H0AA 0.9300 . ?
C0AA C3AA 1.374(3) . ?
C3AA H3AA 0.9300 . ?
C3AA C1BA 1.397(4) . ?
C3BA H3BA 0.9300 . ?
C3BA C1BA 1.382(4) . ?
C1BA H1BA 0.9300 . ?
C4BA H4BA 0.9700 . ?
C4BA H4BB 0.9700 . ?
C4BA C5BA 1.470(12) . ?
C4BA C4CA 1.438(13) . ?
C7BA H7BA 0.9700 . ?
C7BA H7BB 0.9700 . ?
C7BA C6BA 1.425(12) . ?
C7BA C8BA 1.490(12) . ?
C6BA H6BA 0.9700 . ?
C6BA H6BB 0.9700 . ?
C6BA C5BA 1.474(12) . ?
C8BA H8BA 0.9600 . ?
C8BA H8BB 0.9600 . ?
C8BA H8BC 0.9600 . ?
C5BA H5BA 0.9700 . ?
C5BA H5BB 0.9700 . ?
C1CA H1CA 0.9700 . ?
C1CA H1CB 0.9700 . ?
C1CA C0CA 1.402(10) . ?
C0CA H0CA 0.9700 . ?
C0CA H0CB 0.9700 . ?
C0CA C9BA 1.652(11) . ?
C9BA H9BA 0.9700 . ?
C9BA H9BB 0.9700 . ?
C2CA H2CA 0.9700 . ?
C2CA H2CB 0.9700 . ?
C2CA C3CA 1.494(8) . ?
C3CA H3CA 0.9700 . ?
C3CA H3CB 0.9700 . ?
C4CA H4CA 0.9700 . ?
C4CA H4CB 0.9700 . ?
C4CA C5CA 1.451(15) . ?
C5CA H5CA 0.9700 . ?
C5CA H5CB 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
-0.5980 -3.3338 8.0042 -0.1482 -0.0114 -0.9889
1.6257 3.0457 -7.9190 0.2912 0.0227 0.9564
0.1819 6.1254 1.5499 -0.0254 -0.9785 -0.2048
-0.0940 -6.9692 0.0022 0.0260 0.9996 0.0089
-0.3998 3.5631 -7.9234 0.0080 -0.0026 1.0000
0.0601 -3.6427 7.9689 -0.0550 0.0193 -0.9983
5.3633 -1.0909 4.4007 0.7024 -0.2487 -0.6669
-2.8115 2.7217 -6.9966 -0.3310 0.1173 0.9363
