#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:09:35 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250059 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/44/4134445.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_4134445
loop_
_publ_author_name
'Sheng, Xinru'
'Li, Errui'
'Zhou, Yujuan'
'Zhao, Run'
'Zhu, Weijie'
'Huang, Feihe'
_publ_section_title
;
 Separation of 2-Chloropyridine/3-Chloropyridine by Nonporous Adaptive
 Crystals of Pillararenes with Different Substituents and Cavity Sizes.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6360
_journal_page_last               6364
_journal_paper_doi               10.1021/jacs.0c01274
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C66 H72 Br12 O12, C5 H4 Cl N'
_chemical_formula_sum            'C71 H76 Br12 Cl N O12'
_chemical_formula_weight         2129.69
_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
_audit_creation_date             2019-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                117.9100(10)
_cell_angle_beta                 100.4210(10)
_cell_angle_gamma                94.4500(10)
_cell_formula_units_Z            1
_cell_length_a                   13.3514(3)
_cell_length_b                   13.3868(3)
_cell_length_c                   13.8133(3)
_cell_measurement_reflns_used    9030
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.910
_cell_measurement_theta_min      3.832
_cell_volume                     2108.00(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      170.01
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24602
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.952
_diffrn_reflns_theta_min         4.329
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.169
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1387 before and 0.0867 after correction. The Ratio of minimum to maximum transmission is 0.6769. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_description       block
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.909
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.063(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         7778
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.1186
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1381P)²+10.4643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3020
_refine_ls_wR_factor_ref         0.3048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7212
_reflns_number_total             7778
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c01274_si_002.cif
_cod_data_source_block           20181225sxr1_1
_cod_depositor_comments
'Adding full bibliography for 4134442--4134445.cif.'
_cod_database_code               4134445
_shelx_shelxl_version_number     2018/3
_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   0.358
_shelx_estimated_absorpt_t_min   0.316
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C41-C40
 1.53 with sigma of 0.02
 C45-C44
 1.53 with sigma of 0.02
 C13-C12
 1.53 with sigma of 0.02
 Br3-C13
 1.8 with sigma of 0.02
 Br9-C41
 1.8 with sigma of 0.02
 C43-C42
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim N1 \\sim C017 \\sim C019 \\sim C5AA \\sim C5BA \\sim C01D: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Br9 \\sim O9 \\sim C40 \\sim C41: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br3 \\sim C12 \\sim C13: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Br4 \\sim O1 \\sim C14 \\sim C15: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Br11 \\sim C44 \\sim C45: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Br10 \\sim O11 \\sim C42 \\sim C43: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C34 \\sim Br9 \\sim O9 \\sim C40 \\sim C41: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
O10 \\sim C38 \\sim C39: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C23 \\sim C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Br7(0.5) H3(0.5) H4(0.5) H6(0.5) H7(0.5) H18(0.5) H19(0.5)
 H21(0.5) H22(0.5) H33(0.5) H34(0.5) H36(0.5) H37(0.5) Br1(0.5) Br2(0.5)
 Br5(0.5) Br6(0.5) Br9(0.5) O3(0.5) O4(0.5) O7(0.5) O8(0.5) O9(0.5) O10(0.5)
 C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5)
 H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5)
 H24A(0.5) H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5)
 C38(0.5) H38A(0.5) H38B(0.5) C39(0.5) H39A(0.5) H39B(0.5) C40(0.5) H40A(0.5)
 H40B(0.5) C41(0.5) H41A(0.5) H41B(0.5) Br3(0.5) Br4(0.5) Br8(0.5) Br10(0.5)
 Br11(0.5) O1(0.5) O2(0.5) O5(0.5) O6(0.5) O11(0.5) O12(0.5) C12(0.5) H12A(0.5)
 H12B(0.5) C13(0.5) H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C15(0.5)
 H15A(0.5) H15B(0.5) C27(0.5) H27A(0.5) H27B(0.5) C28(0.5) H28A(0.5) H28B(0.5)
 C29(0.5) H29A(0.5) H29B(0.5) C30(0.5) H30A(0.5) H30B(0.5) C42(0.5) H42A(0.5)
 H42B(0.5) C43(0.5) H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5) C45(0.5)
 H45A(0.5) H45B(0.5) Cl1(0.5) C019(0.5) C017(0.5) H017(0.5) C01D(0.5) H01D(0.5)
 C5AA(0.5) H5AA(0.5) C5BA(0.5) H5BA(0.5) N1(0.5) Br7A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C16(H16A,H16B), C31(H31A,H31B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,
 H41B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C42(H42A,H42B),
  C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C18(H18), C19(H19), C21(H21), C22(H22),
 C33(H33), C34(H34), C36(H36), C37(H37), C017(H017), C01D(H01D), C5AA(H5AA),
 C5BA(H5BA)
5.c Fitted hexagon refined as free rotating group:
 C019(C017,C01D,C5AA,C5BA,N1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br7 Br 0.8709(4) 0.3144(4) 0.1510(5) 0.1077(17) Uani 0.5 1 d . . P A 1
C1 C 0.5910(5) 0.9996(5) 0.7778(5) 0.0424(13) Uani 1 1 d . . . . .
H1A H 0.660878 1.047426 0.819502 0.051 Uiso 1 1 calc R . . . .
H1B H 0.540211 1.051826 0.793546 0.051 Uiso 1 1 calc R . . . .
C2 C 0.5855(5) 0.9406(5) 0.6528(5) 0.0392(13) Uani 1 1 d . . . . .
C3 C 0.4905(5) 0.8963(5) 0.5729(6) 0.0427(14) Uani 1 1 d . . . . .
H3 H 0.428056 0.901362 0.597403 0.051 Uiso 0.5 1 calc R . P B 1
C4 C 0.4858(5) 0.8453(5) 0.4589(6) 0.0443(14) Uani 1 1 d . . . . .
H4 H 0.420166 0.814475 0.405984 0.053 Uiso 0.5 1 calc R . P C 2
C5 C 0.5753(5) 0.8384(5) 0.4203(5) 0.0435(14) Uani 1 1 d . . . . .
C6 C 0.6700(5) 0.8817(6) 0.4984(5) 0.0437(14) Uani 1 1 d . . . . .
H6 H 0.732044 0.875750 0.473238 0.052 Uiso 0.5 1 calc R . P D 1
C7 C 0.6756(5) 0.9339(6) 0.6132(6) 0.0444(14) Uani 1 1 d . . . . .
H7 H 0.741387 0.965582 0.665828 0.053 Uiso 0.5 1 calc R . P E 2
C16 C 0.5703(5) 0.7881(6) 0.2947(5) 0.0474(15) Uani 1 1 d . . . . .
H16A H 0.517258 0.818868 0.261879 0.057 Uiso 1 1 calc R . . . .
H16B H 0.638019 0.814352 0.286240 0.057 Uiso 1 1 calc R . . . .
C17 C 0.5447(5) 0.6575(6) 0.2279(5) 0.0429(14) Uani 1 1 d . . . . .
C18 C 0.4462(5) 0.5994(6) 0.1577(5) 0.0422(13) Uani 1 1 d . . . . .
H18 H 0.392959 0.641756 0.154615 0.051 Uiso 0.5 1 calc R . P F 1
C19 C 0.4254(5) 0.4818(5) 0.0931(5) 0.0392(13) Uani 1 1 d . . . . .
H19 H 0.357709 0.444026 0.046263 0.047 Uiso 0.5 1 calc R . P G 2
C20 C 0.5014(5) 0.4163(5) 0.0947(5) 0.0390(13) Uani 1 1 d . . . . .
C21 C 0.5984(5) 0.4741(6) 0.1669(6) 0.0457(14) Uani 1 1 d . . . . .
H21 H 0.650856 0.431533 0.172354 0.055 Uiso 0.5 1 calc R . P H 1
C22 C 0.6198(5) 0.5931(6) 0.2313(6) 0.0466(14) Uani 1 1 d . . . . .
H22 H 0.687277 0.631013 0.278636 0.056 Uiso 0.5 1 calc R . P I 2
C31 C 0.4796(5) 0.2880(6) 0.0191(5) 0.0455(14) Uani 1 1 d . . . . .
H31A H 0.538051 0.265578 -0.016618 0.055 Uiso 1 1 calc R . . . .
H31B H 0.416621 0.266588 -0.042022 0.055 Uiso 1 1 calc R . . . .
C32 C 0.4638(5) 0.2204(5) 0.0791(5) 0.0397(13) Uani 1 1 d . . . . .
C33 C 0.3705(5) 0.2085(5) 0.1078(5) 0.0418(13) Uani 1 1 d . . . . .
H33 H 0.317788 0.247300 0.093990 0.050 Uiso 0.5 1 calc R . P J 1
C34 C 0.3538(4) 0.1398(5) 0.1569(5) 0.0403(13) Uani 1 1 d . U . . .
H34 H 0.289950 0.132826 0.176393 0.048 Uiso 0.5 1 calc R . P K 2
C35 C 0.4302(4) 0.0812(5) 0.1777(5) 0.0364(12) Uani 1 1 d . . . . .
C36 C 0.5240(4) 0.0983(5) 0.1524(5) 0.0378(12) Uani 1 1 d . . . . .
H36 H 0.578035 0.062433 0.169255 0.045 Uiso 0.5 1 calc R . P L 1
C37 C 0.5415(5) 0.1646(5) 0.1045(5) 0.0395(13) Uani 1 1 d . . . . .
H37 H 0.606595 0.173414 0.088020 0.047 Uiso 0.5 1 calc R . P M 2
Br1 Br 0.9575(2) 1.01422(19) 0.8552(2) 0.0550(6) Uani 0.5 1 d . . P N 1
Br2 Br 0.1839(2) 0.7582(2) 0.2021(3) 0.1071(11) Uani 0.5 1 d . . P O 1
Br5 Br 0.9420(2) 0.7821(3) 0.3910(2) 0.0777(8) Uani 0.5 1 d . . P P 1
Br6 Br 0.09266(17) 0.3331(3) 0.0102(4) 0.1115(12) Uani 0.5 1 d . . P Q 1
Br9 Br 0.0446(4) 0.0241(6) 0.1423(5) 0.151(3) Uani 0.5 1 d D U P R -1
O3 O 0.3934(7) 0.7882(9) 0.3769(8) 0.055(2) Uani 0.5 1 d . . P O 1
O4 O 0.7663(8) 0.9813(14) 0.6923(9) 0.079(4) Uani 0.5 1 d . . P N 1
O7 O 0.3265(7) 0.4150(8) 0.0160(8) 0.053(2) Uani 0.5 1 d . . P Q 1
O8 O 0.7116(7) 0.6438(8) 0.3059(8) 0.056(2) Uani 0.5 1 d . . P P 1
O9 O 0.2635(7) 0.1195(8) 0.1806(9) 0.0502(19) Uani 0.5 1 d . U P R -1
O10 O 0.6342(8) 0.1804(9) 0.0722(9) 0.058(2) Uani 0.5 1 d . U P A 1
C8 C 0.8605(11) 0.9775(14) 0.6590(12) 0.054(3) Uani 0.5 1 d . . P N 1
H8A H 0.861624 1.015908 0.612868 0.065 Uiso 0.5 1 calc R . P N 1
H8B H 0.867414 0.896503 0.612701 0.065 Uiso 0.5 1 calc R . P N 1
C9 C 0.9480(11) 1.0372(16) 0.7625(14) 0.066(4) Uani 0.5 1 d . . P N 1
H9A H 1.012586 1.023423 0.736481 0.079 Uiso 0.5 1 calc R . P N 1
H9B H 0.948331 1.120657 0.794470 0.079 Uiso 0.5 1 calc R . P N 1
C10 C 0.3031(11) 0.7903(15) 0.4154(13) 0.063(4) Uani 0.5 1 d . . P O 1
H10A H 0.288926 0.869557 0.451662 0.075 Uiso 0.5 1 calc R . P O 1
H10B H 0.310942 0.763323 0.471463 0.075 Uiso 0.5 1 calc R . P O 1
C11 C 0.2153(12) 0.7113(16) 0.3134(15) 0.072(5) Uani 0.5 1 d . . P O 1
H11A H 0.152200 0.704880 0.339790 0.086 Uiso 0.5 1 calc R . P O 1
H11B H 0.233037 0.633671 0.277064 0.086 Uiso 0.5 1 calc R . P O 1
C23 C 0.7860(12) 0.5777(14) 0.3180(15) 0.070(4) Uani 0.5 1 d . U P P 1
H23A H 0.808590 0.537320 0.247055 0.084 Uiso 0.5 1 calc R . P P 1
H23B H 0.755250 0.519365 0.334443 0.084 Uiso 0.5 1 calc R . P P 1
C24 C 0.8786(13) 0.6589(16) 0.4151(17) 0.082(5) Uani 0.5 1 d . U P P 1
H24A H 0.931637 0.613771 0.423378 0.098 Uiso 0.5 1 calc R . P P 1
H24B H 0.855773 0.694595 0.486315 0.098 Uiso 0.5 1 calc R . P P 1
C25 C 0.2502(10) 0.4781(13) 0.0022(12) 0.050(3) Uani 0.5 1 d . . P Q 1
H25A H 0.273485 0.523586 -0.031868 0.060 Uiso 0.5 1 calc R . P Q 1
H25B H 0.238492 0.531863 0.076548 0.060 Uiso 0.5 1 calc R . P Q 1
C26 C 0.1529(13) 0.3953(14) -0.0728(15) 0.062(4) Uani 0.5 1 d . . P Q 1
H26A H 0.167816 0.332185 -0.140332 0.074 Uiso 0.5 1 calc R . P Q 1
H26B H 0.103453 0.434666 -0.098179 0.074 Uiso 0.5 1 calc R . P Q 1
C38 C 0.7134(11) 0.1247(15) 0.1005(14) 0.062(3) Uani 0.5 1 d . U P A 1
H38A H 0.688065 0.040521 0.061487 0.074 Uiso 0.5 1 calc R . P A 1
H38B H 0.731591 0.153543 0.183048 0.074 Uiso 0.5 1 calc R . P A 1
C39 C 0.8042(12) 0.1497(16) 0.0652(16) 0.070(4) Uani 0.5 1 d . U P A 1
H39A H 0.783363 0.125930 -0.016155 0.084 Uiso 0.5 1 calc R . P A 1
H39B H 0.855475 0.103378 0.074734 0.084 Uiso 0.5 1 calc R . P A 1
C40 C 0.1805(10) 0.1624(14) 0.1473(14) 0.057(3) Uani 0.5 1 d D U P R -1
H40A H 0.150729 0.114274 0.064837 0.068 Uiso 0.5 1 calc R . P R -1
H40B H 0.204856 0.241771 0.163750 0.068 Uiso 0.5 1 calc R . P R -1
C41 C 0.0988(11) 0.1626(13) 0.2089(15) 0.073(3) Uani 0.5 1 d D U P R -1
H41A H 0.047981 0.210257 0.201621 0.088 Uiso 0.5 1 calc R . P R -1
H41B H 0.129732 0.190905 0.289989 0.088 Uiso 0.5 1 calc R . P R -1
Br3 Br 0.2136(2) 0.9997(3) 0.7089(4) 0.0982(13) Uani 0.5 1 d D U P S 2
Br4 Br 0.9510(3) 0.7317(5) 0.4191(7) 0.210(4) Uani 0.5 1 d . U P T 2
Br8 Br 0.15074(16) 0.6886(3) 0.24456(18) 0.0902(8) Uani 0.5 1 d . . P U 2
Br10 Br 0.1311(3) 0.3004(2) -0.0789(3) 0.1202(14) Uani 0.5 1 d . U P V 2
Br11 Br 0.8057(3) 0.0535(5) 0.3416(2) 0.1299(19) Uani 0.5 1 d . U P W -2
O1 O 0.7592(8) 0.8697(13) 0.4605(10) 0.076(3) Uani 0.5 1 d . U P T 2
O2 O 0.4046(7) 0.9059(8) 0.6164(9) 0.055(2) Uani 0.5 1 d . . P S 2
O5 O 0.3720(7) 0.6736(8) 0.1695(8) 0.049(2) Uani 0.5 1 d . . P U 2
O6 O 0.6725(7) 0.4109(8) 0.1743(9) 0.052(2) Uani 0.5 1 d . . P X 2
O11 O 0.3002(7) 0.2744(8) 0.0944(9) 0.048(2) Uani 0.5 1 d . U P V 2
O12 O 0.5969(7) 0.0403(8) 0.1799(8) 0.0442(19) Uani 0.5 1 d . . P W -2
C12 C 0.3073(10) 0.8582(16) 0.5369(17) 0.070(4) Uani 0.5 1 d D U P S 2
H12A H 0.307833 0.779584 0.476930 0.084 Uiso 0.5 1 calc R . P S 2
H12B H 0.291492 0.906131 0.501157 0.084 Uiso 0.5 1 calc R . P S 2
C13 C 0.2256(12) 0.8544(13) 0.6007(15) 0.080(4) Uani 0.5 1 d D U P S 2
H13A H 0.244193 0.808591 0.638177 0.096 Uiso 0.5 1 calc R . P S 2
H13B H 0.157604 0.815107 0.545792 0.096 Uiso 0.5 1 calc R . P S 2
C14 C 0.8557(11) 0.929(2) 0.5415(16) 0.077(4) Uani 0.5 1 d . U P T 2
H14A H 0.868447 0.900410 0.596353 0.092 Uiso 0.5 1 calc R . P T 2
H14B H 0.856916 1.012620 0.583231 0.092 Uiso 0.5 1 calc R . P T 2
C15 C 0.9375(13) 0.902(2) 0.472(2) 0.095(5) Uani 0.5 1 d . U P T 2
H15A H 1.004891 0.953990 0.518098 0.114 Uiso 0.5 1 calc R . P T 2
H15B H 0.915282 0.913172 0.405295 0.114 Uiso 0.5 1 calc R . P T 2
C27 C 0.2769(11) 0.6240(14) 0.0851(13) 0.054(3) Uani 0.5 1 d . . P U 2
H27A H 0.250231 0.546868 0.073056 0.065 Uiso 0.5 1 calc R . P U 2
H27B H 0.287506 0.615448 0.012742 0.065 Uiso 0.5 1 calc R . P U 2
C28 C 0.1983(11) 0.7046(17) 0.1260(14) 0.054(4) Uani 0.5 1 d . . P U 2
H28A H 0.138446 0.684136 0.061918 0.065 Uiso 0.5 1 calc R . P U 2
H28B H 0.231657 0.785344 0.155674 0.065 Uiso 0.5 1 calc R . P U 2
C29 C 0.7744(12) 0.4693(15) 0.2498(15) 0.063(4) Uani 0.5 1 d . . P X 2
H29A H 0.812081 0.512087 0.221070 0.076 Uiso 0.5 1 calc R . P X 2
H29B H 0.767739 0.524712 0.326113 0.076 Uiso 0.5 1 calc R . P X 2
C30 C 0.8298(15) 0.3832(16) 0.2551(19) 0.086(7) Uani 0.5 1 d . . P X 2
H30A H 0.791125 0.342978 0.285508 0.104 Uiso 0.5 1 calc R . P X 2
H30B H 0.898134 0.422452 0.309346 0.104 Uiso 0.5 1 calc R . P X 2
C42 C 0.1998(10) 0.2492(14) 0.1024(16) 0.060(3) Uani 0.5 1 d D U P V 2
H42A H 0.200321 0.265235 0.180144 0.072 Uiso 0.5 1 calc R . P V 2
H42B H 0.169473 0.167043 0.049363 0.072 Uiso 0.5 1 calc R . P V 2
C43 C 0.1368(15) 0.3258(18) 0.072(2) 0.088(4) Uani 0.5 1 d D U P V 2
H43A H 0.167644 0.407351 0.127615 0.105 Uiso 0.5 1 calc R . P V 2
H43B H 0.065326 0.311435 0.079468 0.105 Uiso 0.5 1 calc R . P V 2
C44 C 0.6920(10) 0.0505(13) 0.1487(13) 0.052(3) Uani 0.5 1 d D U P W -2
H44A H 0.726734 0.132124 0.187259 0.062 Uiso 0.5 1 calc R . P W -2
H44B H 0.678997 0.019418 0.065980 0.062 Uiso 0.5 1 calc R . P W -2
C45 C 0.7588(12) -0.0184(15) 0.1850(16) 0.071(4) Uani 0.5 1 d D U P W -2
H45A H 0.819034 -0.027964 0.151036 0.086 Uiso 0.5 1 calc R . P W -2
H45B H 0.718075 -0.095851 0.156753 0.086 Uiso 0.5 1 calc R . P W -2
Cl1 Cl 0.1474(5) 0.4641(7) 0.3941(8) 0.127(2) Uani 0.5 1 d . U P . .
C019 C 0.2745(7) 0.5160(9) 0.4367(8) 0.075(3) Uani 0.5 1 d . U P . .
C017 C 0.3189(9) 0.5823(9) 0.5521(7) 0.056(3) Uani 0.5 1 d G U P . .
H017 H 0.279253 0.588468 0.604618 0.067 Uiso 0.5 1 calc R . P . .
C01D C 0.4213(9) 0.6395(8) 0.5906(6) 0.075(4) Uani 0.5 1 d G U P . .
H01D H 0.451667 0.684765 0.669512 0.090 Uiso 0.5 1 calc R . P . .
C5AA C 0.4793(7) 0.6304(9) 0.5138(9) 0.075(4) Uani 0.5 1 d G U P . .
H5AA H 0.549287 0.669487 0.540148 0.090 Uiso 0.5 1 calc R . P . .
C5BA C 0.4349(8) 0.5641(9) 0.3984(8) 0.072(3) Uani 0.5 1 d G U P . .
H5BA H 0.474496 0.557912 0.345889 0.086 Uiso 0.5 1 calc R . P . .
N1 N 0.3324(9) 0.5069(8) 0.3599(6) 0.070(3) Uani 0.5 1 d G U P . .
Br7A Br 0.8524(3) 0.2675(4) 0.1113(4) 0.0884(11) Uani 0.5 1 d . . P X 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
Br Br -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C35 C1 C2 114.3(5) 2_666 . ?
C3 C2 C1 121.1(6) . . ?
C3 C2 C7 117.7(6) . . ?
C7 C2 C1 121.1(5) . . ?
C4 C3 C2 120.9(6) . . ?
O2 C3 C2 115.2(7) . . ?
O2 C3 C4 123.8(7) . . ?
C3 C4 C5 121.1(6) . . ?
C3 C4 O3 122.4(7) . . ?
C5 C4 O3 116.2(7) . . ?
C4 C5 C16 121.2(6) . . ?
C6 C5 C4 118.6(6) . . ?
C6 C5 C16 120.2(6) . . ?
C5 C6 C7 120.8(6) . . ?
O1 C6 C5 118.9(7) . . ?
O1 C6 C7 120.3(7) . . ?
C6 C7 C2 120.9(6) . . ?
O4 C7 C2 116.5(7) . . ?
O4 C7 C6 122.6(7) . . ?
C17 C16 C5 114.0(5) . . ?
C18 C17 C16 121.2(6) . . ?
C22 C17 C16 120.7(6) . . ?
C22 C17 C18 118.1(6) . . ?
C17 C18 O5 113.2(6) . . ?
C19 C18 C17 120.7(6) . . ?
C19 C18 O5 125.9(6) . . ?
C18 C19 C20 121.5(6) . . ?
C18 C19 O7 124.3(6) . . ?
C20 C19 O7 114.1(6) . . ?
C19 C20 C31 121.1(5) . . ?
C21 C20 C19 117.7(6) . . ?
C21 C20 C31 121.2(6) . . ?
C22 C21 C20 120.8(6) . . ?
O6 C21 C20 118.6(7) . . ?
O6 C21 C22 120.6(7) . . ?
C17 C22 C21 121.2(6) . . ?
O8 C22 C17 120.1(7) . . ?
O8 C22 C21 118.3(7) . . ?
C20 C31 C32 114.2(5) . . ?
C33 C32 C31 120.7(5) . . ?
C33 C32 C37 118.0(5) . . ?
C37 C32 C31 121.2(6) . . ?
C32 C33 C34 120.5(6) . . ?
O11 C33 C32 117.1(6) . . ?
O11 C33 C34 122.2(6) . . ?
C33 C34 C35 120.9(6) . . ?
O9 C34 C33 123.4(6) . . ?
O9 C34 C35 115.6(6) . . ?
C34 C35 C1 120.7(5) . 2_666 ?
C36 C35 C1 121.9(5) . 2_666 ?
C36 C35 C34 117.3(5) . . ?
C35 C36 O12 113.5(6) . . ?
C37 C36 C35 122.5(5) . . ?
C37 C36 O12 124.0(6) . . ?
C32 C37 O10 114.7(7) . . ?
C36 C37 C32 120.7(6) . . ?
C36 C37 O10 124.6(7) . . ?
C4 O3 C10 116.6(10) . . ?
C7 O4 C8 119.8(10) . . ?
C25 O7 C19 116.3(9) . . ?
C22 O8 C23 120.9(9) . . ?
C34 O9 C40 118.1(9) . . ?
C37 O10 C38 114.1(11) . . ?
O4 C8 C9 108.7(11) . . ?
Br1 C9 C8 123.2(13) . . ?
O3 C10 C11 107.1(13) . . ?
C10 C11 Br2 115.3(14) . . ?
O8 C23 C24 108.4(13) . . ?
C23 C24 Br5 112.6(15) . . ?
O7 C25 C26 108.2(12) . . ?
C25 C26 Br6 109.0(10) . . ?
O10 C38 C39 108.3(15) . . ?
C38 C39 Br7 113.4(12) . . ?
O9 C40 C41 110.2(11) . . ?
C40 C41 Br9 101.9(11) . . ?
C6 O1 C14 118.1(12) . . ?
C3 O2 C12 116.3(11) . . ?
C27 O5 C18 115.4(9) . . ?
C21 O6 C29 119.6(10) . . ?
C33 O11 C42 118.0(8) . . ?
C36 O12 C44 114.9(8) . . ?
O2 C12 C13 107.4(14) . . ?
C12 C13 Br3 113.0(12) . . ?
O1 C14 C15 104.8(15) . . ?
C14 C15 Br4 106.8(16) . . ?
O5 C27 C28 108.0(12) . . ?
C27 C28 Br8 109.3(10) . . ?
C30 C29 O6 107.7(13) . . ?
C29 C30 Br7A 115.7(16) . . ?
O11 C42 C43 106.9(12) . . ?
C42 C43 Br10 113.4(15) . . ?
O12 C44 C45 106.3(12) . . ?
C44 C45 Br11 111.6(11) . . ?
C017 C019 Cl1 118.2(7) . . ?
C017 C019 N1 120.0 . . ?
N1 C019 Cl1 121.2(7) . . ?
C01D C017 C019 120.0 . . ?
C017 C01D C5AA 120.0 . . ?
C5BA C5AA C01D 120.0 . . ?
C5AA C5BA N1 120.0 . . ?
C5BA N1 C019 120.0 . . ?
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
Br7 C39 1.981(18) . ?
C1 C2 1.510(9) . ?
C1 C35 1.505(8) 2_666 ?
C2 C3 1.393(8) . ?
C2 C7 1.401(9) . ?
C3 C4 1.379(10) . ?
C3 O2 1.375(13) . ?
C4 C5 1.387(10) . ?
C4 O3 1.388(11) . ?
C5 C6 1.381(9) . ?
C5 C16 1.525(9) . ?
C6 C7 1.386(9) . ?
C6 O1 1.376(14) . ?
C7 O4 1.348(12) . ?
C16 C17 1.519(9) . ?
C17 C18 1.397(8) . ?
C17 C22 1.380(10) . ?
C18 C19 1.370(9) . ?
C18 O5 1.434(11) . ?
C19 C20 1.395(9) . ?
C19 O7 1.447(10) . ?
C20 C21 1.388(9) . ?
C20 C31 1.503(9) . ?
C21 C22 1.387(10) . ?
C21 O6 1.370(11) . ?
C22 O8 1.336(11) . ?
C31 C32 1.512(9) . ?
C32 C33 1.394(9) . ?
C32 C37 1.410(9) . ?
C33 C34 1.401(9) . ?
C33 O11 1.383(10) . ?
C34 C35 1.403(8) . ?
C34 O9 1.346(11) . ?
C35 C36 1.390(9) . ?
C36 C37 1.362(9) . ?
C36 O12 1.398(10) . ?
C37 O10 1.422(12) . ?
Br1 C9 1.438(19) . ?
Br2 C11 1.91(2) . ?
Br5 C24 1.99(2) . ?
Br6 C26 1.943(15) . ?
Br9 C41 1.662(15) . ?
O3 C10 1.400(19) . ?
O4 C8 1.412(17) . ?
O7 C25 1.415(17) . ?
O8 C23 1.418(19) . ?
O9 C40 1.390(15) . ?
O10 C38 1.441(18) . ?
C8 C9 1.49(2) . ?
C10 C11 1.514(19) . ?
C23 C24 1.529(18) . ?
C25 C26 1.49(2) . ?
C38 C39 1.46(2) . ?
C40 C41 1.499(16) . ?
Br3 C13 1.859(15) . ?
Br4 C15 2.08(3) . ?
Br8 C28 1.952(14) . ?
Br10 C43 1.94(3) . ?
Br11 C45 1.861(18) . ?
O1 C14 1.425(18) . ?
O2 C12 1.416(18) . ?
O5 C27 1.422(16) . ?
O6 C29 1.451(16) . ?
O11 C42 1.393(16) . ?
O12 C44 1.429(16) . ?
C12 C13 1.533(16) . ?
C14 C15 1.54(3) . ?
C27 C28 1.55(2) . ?
C29 C30 1.44(2) . ?
C30 Br7A 1.96(2) . ?
C42 C43 1.528(17) . ?
C44 C45 1.515(15) . ?
Cl1 C019 1.668(11) . ?
C019 C017 1.3900 . ?
C019 N1 1.3900 . ?
C017 C01D 1.3900 . ?
C01D C5AA 1.3900 . ?
C5AA C5BA 1.3900 . ?
C5BA N1 1.3900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 178.2(5) . . . . ?
C1 C2 C3 O2 -2.9(9) . . . . ?
C1 C2 C7 C6 -178.7(6) . . . . ?
C1 C2 C7 O4 0.8(11) . . . . ?
C1 C35 C36 C37 175.1(5) 2_666 . . . ?
C1 C35 C36 O12 -4.3(8) 2_666 . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
C2 C3 C4 O3 172.1(7) . . . . ?
C2 C3 O2 C12 -178.0(9) . . . . ?
C2 C7 O4 C8 179.7(12) . . . . ?
C3 C2 C7 C6 -2.0(9) . . . . ?
C3 C2 C7 O4 177.5(9) . . . . ?
C3 C4 C5 C6 1.2(9) . . . . ?
C3 C4 C5 C16 -176.5(6) . . . . ?
C3 C4 O3 C10 3.6(15) . . . . ?
C3 O2 C12 C13 167.8(10) . . . . ?
C4 C3 O2 C12 0.9(13) . . . . ?
C4 C5 C6 C7 -1.7(9) . . . . ?
C4 C5 C6 O1 176.6(9) . . . . ?
C4 C5 C16 C17 -77.8(8) . . . . ?
C4 O3 C10 C11 -173.1(12) . . . . ?
C5 C4 O3 C10 177.1(11) . . . . ?
C5 C6 C7 C2 2.1(9) . . . . ?
C5 C6 C7 O4 -177.3(10) . . . . ?
C5 C6 O1 C14 171.3(13) . . . . ?
C5 C16 C17 C18 104.3(7) . . . . ?
C5 C16 C17 C22 -78.5(8) . . . . ?
C6 C5 C16 C17 104.5(7) . . . . ?
C6 C7 O4 C8 -0.9(19) . . . . ?
C6 O1 C14 C15 -177.3(15) . . . . ?
C7 C2 C3 C4 1.5(8) . . . . ?
C7 C2 C3 O2 -179.5(7) . . . . ?
C7 C6 O1 C14 -10.4(18) . . . . ?
C7 O4 C8 C9 179.2(14) . . . . ?
C16 C5 C6 C7 176.1(6) . . . . ?
C16 C5 C6 O1 -5.6(11) . . . . ?
C16 C17 C18 C19 176.5(5) . . . . ?
C16 C17 C18 O5 -8.7(9) . . . . ?
C16 C17 C22 C21 -177.2(6) . . . . ?
C16 C17 C22 O8 9.8(11) . . . . ?
C17 C18 C19 C20 -0.3(9) . . . . ?
C17 C18 C19 O7 -178.3(7) . . . . ?
C17 C18 O5 C27 167.9(9) . . . . ?
C17 C22 O8 C23 174.0(13) . . . . ?
C18 C17 C22 C21 0.1(10) . . . . ?
C18 C17 C22 O8 -172.9(8) . . . . ?
C18 C19 C20 C21 2.1(8) . . . . ?
C18 C19 C20 C31 -176.7(5) . . . . ?
C18 C19 O7 C25 4.7(13) . . . . ?
C18 O5 C27 C28 167.0(9) . . . . ?
C19 C18 O5 C27 -17.6(13) . . . . ?
C19 C20 C21 C22 -2.8(9) . . . . ?
C19 C20 C21 O6 176.5(7) . . . . ?
C19 C20 C31 C32 -104.3(6) . . . . ?
C19 O7 C25 C26 -175.9(11) . . . . ?
C20 C19 O7 C25 -173.4(9) . . . . ?
C20 C21 C22 C17 1.7(10) . . . . ?
C20 C21 C22 O8 174.9(8) . . . . ?
C20 C21 O6 C29 -179.6(11) . . . . ?
C20 C31 C32 C33 77.4(7) . . . . ?
C20 C31 C32 C37 -104.6(7) . . . . ?
C21 C20 C31 C32 76.9(7) . . . . ?
C21 C22 O8 C23 0.8(17) . . . . ?
C21 O6 C29 C30 170.5(15) . . . . ?
C22 C17 C18 C19 -0.8(9) . . . . ?
C22 C17 C18 O5 174.0(6) . . . . ?
C22 C21 O6 C29 -0.3(15) . . . . ?
C22 O8 C23 C24 -175.8(14) . . . . ?
C31 C20 C21 C22 176.1(6) . . . . ?
C31 C20 C21 O6 -4.7(10) . . . . ?
C31 C32 C33 C34 175.9(6) . . . . ?
C31 C32 C33 O11 -9.3(10) . . . . ?
C31 C32 C37 C36 -176.0(5) . . . . ?
C31 C32 C37 O10 1.7(9) . . . . ?
C32 C33 C34 C35 -0.3(9) . . . . ?
C32 C33 C34 O9 -176.0(8) . . . . ?
C32 C33 O11 C42 168.5(11) . . . . ?
C32 C37 O10 C38 178.9(9) . . . . ?
C33 C32 C37 C36 2.0(9) . . . . ?
C33 C32 C37 O10 179.7(7) . . . . ?
C33 C34 C35 C1 -175.3(5) . . . 2_666 ?
C33 C34 C35 C36 2.8(9) . . . . ?
C33 C34 O9 C40 4.6(15) . . . . ?
C33 O11 C42 C43 -174.3(14) . . . . ?
C34 C33 O11 C42 -16.8(15) . . . . ?
C34 C35 C36 C37 -3.0(8) . . . . ?
C34 C35 C36 O12 177.6(6) . . . . ?
C34 O9 C40 C41 -163.3(11) . . . . ?
C35 C1 C2 C3 77.8(7) 2_666 . . . ?
C35 C1 C2 C7 -105.7(6) 2_666 . . . ?
C35 C34 O9 C40 -171.3(10) . . . . ?
C35 C36 C37 C32 0.6(9) . . . . ?
C35 C36 C37 O10 -176.9(7) . . . . ?
C35 C36 O12 C44 176.4(9) . . . . ?
C36 C37 O10 C38 -3.5(13) . . . . ?
C36 O12 C44 C45 -179.7(10) . . . . ?
C37 C32 C33 C34 -2.1(9) . . . . ?
C37 C32 C33 O11 172.7(7) . . . . ?
C37 C36 O12 C44 -3.0(13) . . . . ?
C37 O10 C38 C39 -178.8(11) . . . . ?
O3 C4 C5 C6 -172.4(7) . . . . ?
O3 C4 C5 C16 9.8(10) . . . . ?
O3 C10 C11 Br2 -64.3(16) . . . . ?
O4 C8 C9 Br1 49(2) . . . . ?
O7 C19 C20 C21 -179.7(7) . . . . ?
O7 C19 C20 C31 1.5(9) . . . . ?
O7 C25 C26 Br6 72.6(14) . . . . ?
O8 C23 C24 Br5 -57.7(19) . . . . ?
O9 C34 C35 C1 0.8(9) . . . 2_666 ?
O9 C34 C35 C36 178.9(7) . . . . ?
O9 C40 C41 Br9 -75.6(14) . . . . ?
O10 C38 C39 Br7 66.2(16) . . . . ?
O1 C6 C7 C2 -176.1(9) . . . . ?
O1 C14 C15 Br4 -73.3(17) . . . . ?
O2 C3 C4 C5 180.0(7) . . . . ?
O2 C12 C13 Br3 63.6(14) . . . . ?
O5 C18 C19 C20 -174.4(7) . . . . ?
O5 C27 C28 Br8 -74.6(13) . . . . ?
O6 C21 C22 C17 -177.5(7) . . . . ?
O6 C29 C30 Br7A 61(2) . . . . ?
O11 C33 C34 C35 -174.8(7) . . . . ?
O11 C42 C43 Br10 60.1(17) . . . . ?
O12 C36 C37 C32 179.9(7) . . . . ?
O12 C44 C45 Br11 -71.0(15) . . . . ?
Cl1 C019 C017 C01D -171.6(9) . . . . ?
Cl1 C019 N1 C5BA 171.3(9) . . . . ?
C019 C017 C01D C5AA 0.0 . . . . ?
C017 C019 N1 C5BA 0.0 . . . . ?
C017 C01D C5AA C5BA 0.0 . . . . ?
C01D C5AA C5BA N1 0.0 . . . . ?
C5AA C5BA N1 C019 0.0 . . . . ?
N1 C019 C017 C01D 0.0 . . . . ?
