#------------------------------------------------------------------------------
#$Date: 2022-01-13 00:55:14 +0200 (Thu, 13 Jan 2022) $
#$Revision: 272007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/95/7129547.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_7129547
loop_
_publ_author_name
'Ni, Dan'
'Song, Longlong'
'Zhao, Yun'
'Liu, Shunying'
_publ_section_title
;
 One-pot Synthesis of Multi-substituted Conjugated Dienones by Trapping
 Allene Carbocation with Active Ylides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06405C
_journal_year                    2022
_chemical_formula_moiety
'0.5(C33 H28 F3 N2 O2 S), 0.5(C33 H30 F3 N2 O2 S)'
_chemical_formula_sum            'C33 H29 F3 N2 O2 S'
_chemical_formula_weight         574.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2022-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.234(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.6154(10)
_cell_length_b                   11.0222(3)
_cell_length_c                   25.2859(12)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      73.1400
_cell_measurement_theta_min      3.1880
_cell_volume                     5951.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00  68.00   1.00    2.00    --    0.00  37.00 120.00   26
  2  ω    -12.00  16.00   1.00    2.00    --    0.00 -37.00 120.00   28
  3  ω    -89.00 -27.00   1.00    2.00    --    0.00 -37.00 120.00   62
  4  ω    -88.00   8.00   1.00    2.00    --    0.00 -37.00-150.00   96
  5  ω    -86.00 -30.00   1.00    2.00    --    0.00 -57.00 -60.00   56
  6  ω    -39.00  17.00   1.00    2.00    --    0.00 -37.00 -30.00   56
  7  ω      9.00  39.00   1.00    4.00    --   95.80 -30.00 -60.00   30
  8  ω      6.00 102.00   1.00    4.00    --   95.80 -82.00  30.00   96
  9  ω     31.00 128.00   1.00    4.00    --   95.80 -82.00-180.00   97
 10  ω     21.00  47.00   1.00    4.00    --   95.80 -82.00 -60.00   26
 11  ω     69.00 121.00   1.00    4.00    --   95.80 -82.00 -60.00   52
 12  ω      6.00  91.00   1.00    4.00    --   95.80 -61.00  90.00   85
 13  ω     76.00 104.00   1.00    4.00    --   95.80 -82.00 -90.00   28
 14  ω      6.00  71.00   1.00    4.00    --   95.80 -15.00-180.00   65
 15  ω      6.00 120.00   1.00    4.00    --   95.80 -61.00-180.00  114
 16  ω      9.00 115.00   1.00    4.00    --   95.80 -45.00 -90.00  106
 17  ω     28.00 111.00   1.00    4.00    --   95.80 -82.00  90.00   83
 18  ω     77.00 123.00   1.00    4.00    --   95.80 -15.00-180.00   46
 19  ω     46.00 106.00   1.00    4.00    --   95.80 -30.00 -60.00   60
 20  ω     12.00  37.00   1.00    4.00    --   95.80 -82.00 150.00   25
 21  ω     78.00 103.00   1.00    4.00    --   95.80 -82.00 150.00   25
 22  ω     54.00 132.00   1.00    4.00    --   95.80   0.00 -60.00   78
 23  ω     40.00 103.00   1.00    4.00    --   95.80 -82.00 -30.00   63
 24  ω    141.00 185.00   1.00    4.00    --   95.80  30.00 -60.00   44
 25  ω     66.00 104.00   1.00    4.00    --   95.80 -82.00   0.00   38
 26  ω    100.00 126.00   1.00    4.00    --   95.80 -82.00  60.00   26
 27  ω      6.00  35.00   1.00    4.00    --   95.80   0.00 -60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0090342000
_diffrn_orient_matrix_UB_12      -0.0583925000
_diffrn_orient_matrix_UB_13      -0.0521754000
_diffrn_orient_matrix_UB_21      0.0538480000
_diffrn_orient_matrix_UB_22      -0.0780199000
_diffrn_orient_matrix_UB_23      0.0379769000
_diffrn_orient_matrix_UB_31      -0.0471704000
_diffrn_orient_matrix_UB_32      -0.1001304000
_diffrn_orient_matrix_UB_33      0.0008507000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            64000
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.199
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.801
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     747
_refine_ls_number_reflns         10529
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.1198
_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)+(0.0933P)²+22.9078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2791
_refine_ls_wR_factor_ref         0.2966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7586
_reflns_number_total             10529
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06405c2.cif
_cod_data_source_block           exp_2265
_cod_database_code               7129547
_shelx_shelxl_version_number     2017/1
_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   0.884
_shelx_estimated_absorpt_t_min   0.591
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Shared sites
{S2, C66}
{S3, C67}
3. Rigid bond restraints
 C33, N1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S1, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C29, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C29, F3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C29, F2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C33 \\sim N1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C29 \\sim F1: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C29 \\sim F3: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C29 \\sim F2: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C33) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(S2) = Uanis(C66)
Uanis(S3) = Uanis(C67)
5. Others
 Fixed Sof: S2(0.5) S3(0.5) C66(0.5) C67(0.5)
6.a Ternary CH refined with riding coordinates:
 C46(H46), C27(H27)
6.b Secondary CH2 refined with riding coordinates:
 C47(H47A,H47B)
6.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C50(H50), C51(H51),
 C53(H53), C54(H54), C56(H56), C57(H57), C59(H59), C60(H60), C2(H2), C3(H3),
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
  C15(H15), C21(H21), C22(H22), C24(H24), C25(H25), C28(H28)
6.d Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,
 H64C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.191
_oxdiff_exptl_absorpt_empirical_full_min 0.355
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.85206(16) 0.2111(3) 0.94863(14) 0.0716(8) Uani 0.5 1 d . . P . .
S3 S 0.89525(12) 0.1621(2) 0.91063(11) 0.0494(6) Uani 0.5 1 d . . P . .
F4 F 0.81058(19) 0.7638(4) 0.60487(15) 0.0708(11) Uani 1 1 d . . . . .
F5 F 0.8866(2) 0.6987(6) 0.6716(2) 0.118(2) Uani 1 1 d . . . . .
F6 F 0.8539(4) 0.8724(5) 0.6752(2) 0.159(3) Uani 1 1 d . . . . .
O3 O 0.72540(16) 0.5751(3) 0.75618(16) 0.0415(9) Uani 1 1 d . . . . .
O4 O 0.82357(15) 0.7041(3) 0.74548(14) 0.0373(8) Uani 1 1 d . . . . .
N3 N 0.6612(3) 0.8702(5) 0.9573(3) 0.0624(15) Uani 1 1 d . . . . .
N4 N 1.0569(2) 1.0286(4) 0.8980(2) 0.0466(12) Uani 1 1 d . . . . .
C34 C 0.6701(2) 0.7478(4) 0.7699(2) 0.0322(11) Uani 1 1 d . . . . .
C35 C 0.6229(2) 0.6791(5) 0.7787(2) 0.0405(12) Uani 1 1 d . . . . .
H35 H 0.628737 0.596022 0.784758 0.049 Uiso 1 1 calc R . . . .
C36 C 0.5680(3) 0.7308(5) 0.7788(3) 0.0508(15) Uani 1 1 d . . . . .
H36 H 0.536922 0.683765 0.785168 0.061 Uiso 1 1 calc R . . . .
C37 C 0.5592(3) 0.8546(5) 0.7691(3) 0.0530(16) Uani 1 1 d . . . . .
H37 H 0.521847 0.890266 0.768831 0.064 Uiso 1 1 calc R . . . .
C38 C 0.6051(3) 0.9250(5) 0.7599(3) 0.0448(13) Uani 1 1 d . . . . .
H38 H 0.598591 1.007585 0.752679 0.054 Uiso 1 1 calc R . . . .
C39 C 0.6614(2) 0.8712(4) 0.7615(2) 0.0363(11) Uani 1 1 d . . . . .
H39 H 0.693279 0.918767 0.756867 0.044 Uiso 1 1 calc R . . . .
C40 C 0.8998(3) 0.2866(5) 0.8761(3) 0.0482(14) Uani 1 1 d . . . . .
C41 C 0.8416(3) 0.3500(5) 0.9314(3) 0.0493(14) Uani 1 1 d . . . . .
C42 C 0.8677(3) 0.3843(4) 0.8912(2) 0.0389(12) Uani 1 1 d . . . . .
C43 C 0.8631(3) 0.5043(5) 0.8686(2) 0.0436(13) Uani 1 1 d . . . . .
C44 C 0.8511(2) 0.6085(4) 0.8546(2) 0.0392(12) Uani 1 1 d . . . . .
C45 C 0.8318(2) 0.7384(4) 0.8418(2) 0.0321(11) Uani 1 1 d . . . . .
C46 C 0.7896(2) 0.7523(4) 0.7794(2) 0.0289(10) Uani 1 1 d . . . . .
H46 H 0.780714 0.838328 0.770601 0.035 Uiso 1 1 calc R . . . .
C47 C 0.7927(3) 0.7154(8) 0.6875(2) 0.0628(19) Uani 1 1 d . . . . .
H47A H 0.756841 0.768807 0.680791 0.075 Uiso 1 1 calc R . . . .
H47B H 0.777594 0.636553 0.671755 0.075 Uiso 1 1 calc R . . . .
C48 C 0.8357(3) 0.7649(5) 0.6602(2) 0.0476(14) Uani 1 1 d . . . . .
C49 C 0.7916(2) 0.7718(5) 0.8776(2) 0.0353(11) Uani 1 1 d . . . . .
C50 C 0.7572(3) 0.6847(5) 0.8951(2) 0.0431(13) Uani 1 1 d . . . . .
H50 H 0.763527 0.602996 0.889464 0.052 Uiso 1 1 calc R . . . .
C51 C 0.7139(3) 0.7168(5) 0.9204(2) 0.0461(13) Uani 1 1 d . . . . .
H51 H 0.690734 0.656849 0.930537 0.055 Uiso 1 1 calc R . . . .
C52 C 0.7043(3) 0.8404(5) 0.9309(2) 0.0464(14) Uani 1 1 d . . . . .
C53 C 0.7412(3) 0.9243(5) 0.9160(2) 0.0479(14) Uani 1 1 d . . . . .
H53 H 0.737738 1.005815 0.923957 0.057 Uiso 1 1 calc R . . . .
C54 C 0.7829(3) 0.8906(5) 0.8895(2) 0.0414(12) Uani 1 1 d . . . . .
H54 H 0.806025 0.950491 0.879298 0.050 Uiso 1 1 calc R . . . .
C55 C 0.8908(2) 0.8177(4) 0.8552(2) 0.0289(10) Uani 1 1 d . . . . .
C56 C 0.9010(2) 0.9010(4) 0.8183(2) 0.0343(11) Uani 1 1 d . . . . .
H56 H 0.871141 0.910082 0.783010 0.041 Uiso 1 1 calc R . . . .
C57 C 0.9551(2) 0.9720(4) 0.8328(2) 0.0376(12) Uani 1 1 d . . . . .
H57 H 0.960206 1.028398 0.807263 0.045 Uiso 1 1 calc R . . . .
C58 C 1.0018(2) 0.9596(4) 0.8850(2) 0.0356(11) Uani 1 1 d . . . . .
C59 C 0.9913(2) 0.8779(5) 0.9222(3) 0.0446(13) Uani 1 1 d . . . . .
H59 H 1.020926 0.869244 0.957666 0.054 Uiso 1 1 calc R . . . .
C60 C 0.9366(2) 0.8075(5) 0.9074(2) 0.0398(12) Uani 1 1 d . . . . .
H60 H 0.930797 0.752716 0.933232 0.048 Uiso 1 1 calc R . . . .
C61 C 1.0924(3) 1.0508(6) 0.9557(3) 0.069(2) Uani 1 1 d . . . . .
H61A H 1.066182 1.090010 0.973723 0.103 Uiso 1 1 calc GR . . . .
H61B H 1.127389 1.102146 0.957930 0.103 Uiso 1 1 calc GR . . . .
H61C H 1.107204 0.975156 0.974096 0.103 Uiso 1 1 calc GR . . . .
C62 C 1.0609(3) 1.1220(5) 0.8589(3) 0.0521(15) Uani 1 1 d . . . . .
H62A H 1.055320 1.086090 0.822955 0.078 Uiso 1 1 calc GR . . . .
H62B H 1.101243 1.160295 0.872452 0.078 Uiso 1 1 calc GR . . . .
H62C H 1.028819 1.181540 0.855294 0.078 Uiso 1 1 calc GR . . . .
C63 C 0.6463(4) 0.9943(6) 0.9651(4) 0.086(3) Uani 1 1 d . . . . .
H63A H 0.683593 1.042624 0.974101 0.129 Uiso 1 1 calc GR . . . .
H63B H 0.629164 0.999037 0.995080 0.129 Uiso 1 1 calc GR . . . .
H63C H 0.616096 1.024060 0.931205 0.129 Uiso 1 1 calc GR . . . .
C64 C 0.6147(4) 0.7825(7) 0.9592(4) 0.075(2) Uani 1 1 d . . . . .
H64A H 0.594775 0.750077 0.922372 0.113 Uiso 1 1 calc GR . . . .
H64B H 0.583970 0.821033 0.972139 0.113 Uiso 1 1 calc GR . . . .
H64C H 0.634493 0.718027 0.984309 0.113 Uiso 1 1 calc GR . . . .
C65 C 0.7273(2) 0.6817(4) 0.7676(2) 0.0320(11) Uani 1 1 d . . . . .
S1 S 0.23548(12) 0.14578(17) 0.55758(10) 0.0860(7) Uani 1 1 d . U . . .
F1 F 0.4224(3) 0.8083(7) 0.7976(3) 0.1294(15) Uani 1 1 d . U . . .
F2 F 0.4217(2) 0.7270(6) 0.8772(3) 0.1182(14) Uani 1 1 d . U . . .
F3 F 0.4370(3) 0.6394(7) 0.8065(3) 0.1283(14) Uani 1 1 d . U . . .
O1 O 0.2161(2) 0.5339(4) 0.7405(2) 0.0578(12) Uani 1 1 d . . . . .
O2 O 0.31656(18) 0.6684(4) 0.74008(18) 0.0573(11) Uani 1 1 d . . . . .
N1 N -0.0145(3) 0.8641(6) 0.5558(3) 0.0822(19) Uani 1 1 d . U . . .
N2 N 0.4120(2) 0.9828(4) 0.5701(2) 0.0448(11) Uani 1 1 d . . . . .
C1 C 0.1527(3) 0.7025(5) 0.7403(2) 0.0419(13) Uani 1 1 d . . . . .
C2 C 0.0993(3) 0.6344(5) 0.7339(3) 0.0510(15) Uani 1 1 d . . . . .
H2 H 0.098324 0.553108 0.723698 0.061 Uiso 1 1 calc R . . . .
C3 C 0.0476(3) 0.6856(7) 0.7424(3) 0.0628(18) Uani 1 1 d . . . . .
H3 H 0.011731 0.639773 0.737581 0.075 Uiso 1 1 calc R . . . .
C4 C 0.0498(4) 0.8061(8) 0.7581(4) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.015336 0.840481 0.764797 0.099 Uiso 1 1 calc R . . . .
C5 C 0.1023(4) 0.8762(8) 0.7642(4) 0.088(3) Uani 1 1 d . . . . .
H5 H 0.103242 0.957516 0.774194 0.105 Uiso 1 1 calc R . . . .
C6 C 0.1535(3) 0.8227(6) 0.7550(3) 0.0647(19) Uani 1 1 d . . . . .
H6 H 0.189048 0.868974 0.758808 0.078 Uiso 1 1 calc R . . . .
C7 C 0.1738(3) 0.7508(5) 0.6214(2) 0.0438(13) Uani 1 1 d . . . . .
C8 C 0.1248(3) 0.6646(6) 0.6037(3) 0.0568(16) Uani 1 1 d . . . . .
H8 H 0.134009 0.582138 0.605957 0.068 Uiso 1 1 calc R . . . .
C9 C 0.0628(3) 0.7030(6) 0.5831(3) 0.0590(17) Uani 1 1 d . . . . .
H9 H 0.030707 0.646087 0.572125 0.071 Uiso 1 1 calc R . . . .
C10 C 0.0486(3) 0.8272(7) 0.5787(3) 0.0663(19) Uani 1 1 d . . . . .
C11 C 0.0957(3) 0.9075(6) 0.5935(3) 0.070(2) Uani 1 1 d . . . . .
H11 H 0.087179 0.990234 0.589981 0.084 Uiso 1 1 calc R . . . .
C12 C 0.1578(3) 0.8672(6) 0.6140(3) 0.0631(18) Uani 1 1 d . . . . .
H12 H 0.189541 0.924892 0.622966 0.076 Uiso 1 1 calc R . . . .
C13 C 0.3154(4) 0.3125(6) 0.5891(4) 0.074(2) Uani 1 1 d . . . . .
H13 H 0.353052 0.354551 0.597620 0.089 Uiso 1 1 calc R . . . .
C14 C 0.3064(4) 0.1981(7) 0.5676(4) 0.084(3) Uani 1 1 d . . . . .
H14 H 0.337356 0.154020 0.559325 0.101 Uiso 1 1 calc R . . . .
C15 C 0.2126(4) 0.2766(7) 0.5800(3) 0.0689(19) Uani 1 1 d . U . . .
H15 H 0.172291 0.290374 0.580595 0.083 Uiso 1 1 calc R . . . .
C16 C 0.2603(4) 0.3603(6) 0.5972(3) 0.0623(18) Uani 1 1 d . . . . .
C17 C 0.2565(3) 0.4820(6) 0.6186(3) 0.0650(19) Uani 1 1 d . . . . .
C18 C 0.2481(3) 0.5799(5) 0.6330(3) 0.0500(15) Uani 1 1 d . . . . .
C19 C 0.2413(3) 0.7074(4) 0.6496(2) 0.0396(12) Uani 1 1 d . . . . .
C20 C 0.2863(2) 0.7848(4) 0.6296(2) 0.0359(11) Uani 1 1 d . . . . .
C21 C 0.3293(3) 0.8649(4) 0.6641(2) 0.0412(13) Uani 1 1 d . . . . .
H21 H 0.330362 0.875396 0.700848 0.049 Uiso 1 1 calc R . . . .
C22 C 0.3711(3) 0.9303(5) 0.6447(2) 0.0422(13) Uani 1 1 d . . . . .
H22 H 0.399483 0.982912 0.668912 0.051 Uiso 1 1 calc R . . . .
C23 C 0.3709(2) 0.9179(4) 0.5899(2) 0.0365(12) Uani 1 1 d . . . . .
C24 C 0.3250(2) 0.8409(5) 0.5544(2) 0.0385(12) Uani 1 1 d . . . . .
H24 H 0.321986 0.833221 0.516988 0.046 Uiso 1 1 calc R . . . .
C25 C 0.2843(2) 0.7768(5) 0.5745(2) 0.0372(11) Uani 1 1 d . . . . .
H25 H 0.254654 0.726584 0.550113 0.045 Uiso 1 1 calc R . . . .
C26 C 0.2077(3) 0.6409(5) 0.7322(2) 0.0431(13) Uani 1 1 d . . . . .
C27 C 0.2553(2) 0.7136(5) 0.7136(2) 0.0416(13) Uani 1 1 d . . . . .
H27 H 0.253854 0.798572 0.724435 0.050 Uiso 1 1 calc R . . . .
C28 C 0.3380(4) 0.6784(12) 0.7993(3) 0.116(4) Uani 1 1 d . . . . .
H28 H 0.314471 0.653217 0.821375 0.140 Uiso 1 1 calc R . . . .
C29 C 0.3967(5) 0.7287(13) 0.8212(5) 0.1217(13) Uani 1 1 d . U . . .
C30 C 0.4307(3) 0.9295(6) 0.5251(3) 0.0555(16) Uani 1 1 d . . . . .
H30A H 0.453909 0.856271 0.538291 0.083 Uiso 1 1 calc GR . . . .
H30B H 0.456473 0.985964 0.513688 0.083 Uiso 1 1 calc GR . . . .
H30C H 0.394082 0.911077 0.493821 0.083 Uiso 1 1 calc GR . . . .
C31 C 0.4628(3) 1.0488(7) 0.6113(3) 0.069(2) Uani 1 1 d . . . . .
H31A H 0.445475 1.111126 0.628294 0.104 Uiso 1 1 calc GR . . . .
H31B H 0.489473 1.084961 0.592955 0.104 Uiso 1 1 calc GR . . . .
H31C H 0.486773 0.993549 0.639602 0.104 Uiso 1 1 calc GR . . . .
C32 C -0.0634(4) 0.7735(9) 0.5485(5) 0.108(3) Uani 1 1 d . . . . .
H32A H -0.052265 0.701002 0.532977 0.162 Uiso 1 1 calc GR . . . .
H32B H -0.102268 0.804416 0.523596 0.162 Uiso 1 1 calc GR . . . .
H32C H -0.067816 0.755401 0.584153 0.162 Uiso 1 1 calc GR . . . .
C66 C 0.85206(16) 0.2111(3) 0.94863(14) 0.0716(8) Uani 0.5 1 d . . P . .
C33 C -0.0330(5) 0.9807(9) 0.5721(5) 0.108(3) Uani 1 1 d . U . . .
H33A H -0.011156 0.994384 0.611219 0.163 Uiso 1 1 calc GR . . . .
H33B H -0.077285 0.980909 0.565454 0.163 Uiso 1 1 calc GR . . . .
H33C H -0.022649 1.043800 0.550513 0.163 Uiso 1 1 calc GR . . . .
C67 C 0.89525(12) 0.1621(2) 0.91063(11) 0.0494(6) Uani 0.5 1 d . . P . .
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C41 S2 S3 102.5(3) . . ?
C40 S3 S2 100.7(3) . . ?
C47 O4 C46 114.3(4) . . ?
C52 N3 C63 121.5(6) . . ?
C52 N3 C64 119.5(5) . . ?
C63 N3 C64 115.3(5) . . ?
C58 N4 C61 119.0(5) . . ?
C58 N4 C62 118.4(5) . . ?
C61 N4 C62 115.6(5) . . ?
C35 C34 C65 117.4(4) . . ?
C39 C34 C35 119.0(5) . . ?
C39 C34 C65 123.6(4) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 C34 121.3(5) . . ?
C36 C35 H35 119.3 . . ?
C35 C36 H36 120.4 . . ?
C35 C36 C37 119.2(5) . . ?
C37 C36 H36 120.4 . . ?
C36 C37 H37 119.6 . . ?
C38 C37 C36 120.8(5) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 H38 120.4 . . ?
C37 C38 C39 119.2(5) . . ?
C39 C38 H38 120.4 . . ?
C34 C39 C38 120.5(5) . . ?
C34 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C42 C40 S3 111.3(4) . . ?
C42 C41 S2 113.7(5) . . ?
C40 C42 C43 124.8(5) . . ?
C41 C42 C40 111.7(5) . . ?
C41 C42 C43 123.5(5) . . ?
C44 C43 C42 167.7(6) . . ?
C43 C44 C45 173.3(6) . . ?
C44 C45 C46 110.4(4) . . ?
C44 C45 C49 106.9(4) . . ?
C44 C45 C55 108.9(4) . . ?
C49 C45 C46 107.0(4) . . ?
C49 C45 C55 112.1(4) . . ?
C55 C45 C46 111.3(4) . . ?
O4 C46 C45 107.5(4) . . ?
O4 C46 H46 109.6 . . ?
O4 C46 C65 109.4(4) . . ?
C45 C46 H46 109.6 . . ?
C65 C46 C45 111.1(4) . . ?
C65 C46 H46 109.6 . . ?
O4 C47 H47A 109.6 . . ?
O4 C47 H47B 109.6 . . ?
O4 C47 C48 110.1(5) . . ?
H47A C47 H47B 108.2 . . ?
C48 C47 H47A 109.6 . . ?
C48 C47 H47B 109.6 . . ?
F4 C48 C47 111.9(5) . . ?
F5 C48 F4 105.5(5) . . ?
F5 C48 C47 111.0(6) . . ?
F6 C48 F4 107.9(5) . . ?
F6 C48 F5 106.2(7) . . ?
F6 C48 C47 113.8(6) . . ?
C50 C49 C45 121.7(5) . . ?
C54 C49 C45 121.2(4) . . ?
C54 C49 C50 116.9(5) . . ?
C49 C50 H50 119.2 . . ?
C51 C50 C49 121.6(5) . . ?
C51 C50 H50 119.2 . . ?
C50 C51 H51 119.7 . . ?
C50 C51 C52 120.6(5) . . ?
C52 C51 H51 119.7 . . ?
N3 C52 C51 119.5(5) . . ?
C53 C52 N3 123.8(5) . . ?
C53 C52 C51 116.7(5) . . ?
C52 C53 H53 119.1 . . ?
C54 C53 C52 121.8(5) . . ?
C54 C53 H53 119.1 . . ?
C49 C54 C53 122.4(5) . . ?
C49 C54 H54 118.8 . . ?
C53 C54 H54 118.8 . . ?
C56 C55 C45 123.7(4) . . ?
C56 C55 C60 117.3(4) . . ?
C60 C55 C45 119.0(4) . . ?
C55 C56 H56 119.3 . . ?
C55 C56 C57 121.5(5) . . ?
C57 C56 H56 119.3 . . ?
C56 C57 H57 119.4 . . ?
C56 C57 C58 121.1(5) . . ?
C58 C57 H57 119.4 . . ?
C57 C58 N4 120.2(5) . . ?
C59 C58 N4 122.3(5) . . ?
C59 C58 C57 117.5(5) . . ?
C58 C59 H59 119.5 . . ?
C58 C59 C60 120.9(5) . . ?
C60 C59 H59 119.5 . . ?
C55 C60 C59 121.7(5) . . ?
C55 C60 H60 119.2 . . ?
C59 C60 H60 119.2 . . ?
N4 C61 H61A 109.5 . . ?
N4 C61 H61B 109.5 . . ?
N4 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
N4 C62 H62A 109.5 . . ?
N4 C62 H62B 109.5 . . ?
N4 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
N3 C63 H63A 109.5 . . ?
N3 C63 H63B 109.5 . . ?
N3 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
N3 C64 H64A 109.5 . . ?
N3 C64 H64B 109.5 . . ?
N3 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
O3 C65 C34 121.2(4) . . ?
O3 C65 C46 119.6(4) . . ?
C34 C65 C46 119.3(4) . . ?
C14 S1 C15 92.3(4) . . ?
C27 O2 C28 114.4(5) . . ?
C10 N1 C32 118.5(7) . . ?
C10 N1 C33 119.0(7) . . ?
C33 N1 C32 111.5(7) . . ?
C23 N2 C30 118.2(5) . . ?
C23 N2 C31 117.4(5) . . ?
C30 N2 C31 113.1(5) . . ?
C2 C1 C26 118.2(5) . . ?
C6 C1 C2 119.2(5) . . ?
C6 C1 C26 122.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(7) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 121.2(7) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C19 119.6(5) . . ?
C12 C7 C8 117.0(6) . . ?
C12 C7 C19 123.4(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 N1 119.2(7) . . ?
C11 C10 N1 121.9(7) . . ?
C11 C10 C9 118.8(6) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(7) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 123.6(7) . . ?
C7 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C14 C13 H13 124.0 . . ?
C14 C13 C16 112.1(8) . . ?
C16 C13 H13 124.0 . . ?
S1 C14 H14 123.3 . . ?
C13 C14 S1 113.3(6) . . ?
C13 C14 H14 123.3 . . ?
S1 C15 H15 123.7 . . ?
C16 C15 S1 112.6(5) . . ?
C16 C15 H15 123.7 . . ?
C13 C16 C17 123.5(7) . . ?
C15 C16 C13 109.7(6) . . ?
C15 C16 C17 126.8(6) . . ?
C18 C17 C16 174.1(9) . . ?
C17 C18 C19 175.6(6) . . ?
C7 C19 C20 109.9(4) . . ?
C7 C19 C27 107.5(4) . . ?
C18 C19 C7 110.1(5) . . ?
C18 C19 C20 106.9(4) . . ?
C18 C19 C27 109.4(4) . . ?
C20 C19 C27 113.0(4) . . ?
C21 C20 C19 123.3(5) . . ?
C25 C20 C19 119.5(5) . . ?
C25 C20 C21 117.2(5) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(5) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
N2 C23 C22 121.7(5) . . ?
N2 C23 C24 121.3(5) . . ?
C22 C23 C24 116.9(5) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.9(5) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 122.3(5) . . ?
C20 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
O1 C26 C1 120.9(5) . . ?
O1 C26 C27 118.7(5) . . ?
C1 C26 C27 120.4(5) . . ?
O2 C27 C19 108.2(4) . . ?
O2 C27 C26 110.3(4) . . ?
O2 C27 H27 108.8 . . ?
C19 C27 H27 108.8 . . ?
C26 C27 C19 112.1(5) . . ?
C26 C27 H27 108.8 . . ?
O2 C28 H28 123.1 . . ?
C29 C28 O2 113.8(8) . . ?
C29 C28 H28 123.1 . . ?
F1 C29 F2 113.4(10) . . ?
F1 C29 F3 85.9(8) . . ?
F1 C29 C28 127.3(10) . . ?
F2 C29 F3 100.2(8) . . ?
F2 C29 C28 115.7(9) . . ?
C28 C29 F3 103.0(11) . . ?
N2 C30 H30A 109.5 . . ?
N2 C30 H30B 109.5 . . ?
N2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 C31 H31A 109.5 . . ?
N2 C31 H31B 109.5 . . ?
N2 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N1 C33 H33A 109.5 . . ?
N1 C33 H33B 109.5 . . ?
N1 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
S2 S3 1.669(4) . ?
S2 C41 1.589(6) . ?
S3 C40 1.648(6) . ?
F4 C48 1.325(7) . ?
F5 C48 1.312(7) . ?
F6 C48 1.271(7) . ?
O3 C65 1.207(6) . ?
O4 C46 1.427(5) . ?
O4 C47 1.406(7) . ?
N3 C52 1.390(7) . ?
N3 C63 1.438(8) . ?
N3 C64 1.439(9) . ?
N4 C58 1.402(6) . ?
N4 C61 1.437(8) . ?
N4 C62 1.451(8) . ?
C34 C35 1.386(7) . ?
C34 C39 1.381(7) . ?
C34 C65 1.502(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.367(7) . ?
C36 H36 0.9300 . ?
C36 C37 1.388(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.376(8) . ?
C38 H38 0.9300 . ?
C38 C39 1.393(7) . ?
C39 H39 0.9300 . ?
C40 C42 1.418(7) . ?
C41 C42 1.388(8) . ?
C42 C43 1.431(7) . ?
C43 C44 1.206(8) . ?
C44 C45 1.501(7) . ?
C45 C46 1.560(7) . ?
C45 C49 1.524(7) . ?
C45 C55 1.537(6) . ?
C46 H46 0.9800 . ?
C46 C65 1.550(6) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.472(8) . ?
C49 C50 1.397(7) . ?
C49 C54 1.372(7) . ?
C50 H50 0.9300 . ?
C50 C51 1.381(8) . ?
C51 H51 0.9300 . ?
C51 C52 1.418(8) . ?
C52 C53 1.379(8) . ?
C53 H53 0.9300 . ?
C53 C54 1.375(8) . ?
C54 H54 0.9300 . ?
C55 C56 1.382(7) . ?
C55 C60 1.388(7) . ?
C56 H56 0.9300 . ?
C56 C57 1.395(7) . ?
C57 H57 0.9300 . ?
C57 C58 1.400(7) . ?
C58 C59 1.379(8) . ?
C59 H59 0.9300 . ?
C59 C60 1.403(7) . ?
C60 H60 0.9300 . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
S1 C14 1.645(9) . ?
S1 C15 1.691(7) . ?
F1 C29 1.300(12) . ?
F2 C29 1.342(13) . ?
F3 C29 1.470(14) . ?
O1 C26 1.202(6) . ?
O2 C27 1.416(7) . ?
O2 C28 1.419(9) . ?
N1 C10 1.412(9) . ?
N1 C32 1.455(10) . ?
N1 C33 1.452(10) . ?
N2 C23 1.390(6) . ?
N2 C30 1.462(7) . ?
N2 C31 1.465(8) . ?
C1 C2 1.385(8) . ?
C1 C6 1.374(8) . ?
C1 C26 1.491(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(8) . ?
C7 C12 1.329(8) . ?
C7 C19 1.533(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.403(9) . ?
C10 C11 1.341(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.399(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.361(10) . ?
C13 C16 1.430(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.376(10) . ?
C16 C17 1.460(9) . ?
C17 C18 1.174(8) . ?
C18 C19 1.489(7) . ?
C19 C20 1.536(7) . ?
C19 C27 1.545(8) . ?
C20 C21 1.389(8) . ?
C20 C25 1.381(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.398(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(7) . ?
C23 C24 1.410(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.534(7) . ?
C27 H27 0.9800 . ?
C28 H28 0.9300 . ?
C28 C29 1.376(13) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 91.4 7.9 ?
2 0.500 0.000 0.000 91.4 7.9 ?
