#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:56:11 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557669.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_1557669
loop_
_publ_author_name
'Wang, Haoran'
'Xing, Hao'
'Gong, Junyi'
'Zhang, Haoke'
'Zhang, Jun'
'Wei, Peifa'
'Yang, Guojian'
'Lam, Jacky W. Y.'
'Lu, Ran'
'Tang, Ben Zhong'
_publ_section_title
;
 “Living” luminogens: light driven ACQ-to-AIE transformation
 accompanied with solid-state actuation
;
_journal_issue                   6
_journal_name_full               'Materials Horizons'
_journal_page_first              1566
_journal_page_last               1572
_journal_paper_doi               10.1039/D0MH00447B
_journal_volume                  7
_journal_year                    2020
_chemical_formula_moiety         'C30 H20 F2 N2 O2'
_chemical_formula_sum            'C30 H20 F2 N2 O2'
_chemical_formula_weight         478.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-30 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6152(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7576(3)
_cell_length_b                   9.38142(11)
_cell_length_c                   22.7647(3)
_cell_measurement_reflns_used    14729
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6460
_cell_measurement_theta_min      4.1110
_cell_volume                     4581.39(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 130.00   1.00    3.00    --  104.49 -61.00   0.00   98
  2  ω   -110.00 -15.00   1.00    2.00    --  -40.57 -37.00  60.00   95
  3  ω    -67.00  36.00   1.00    2.00    --  -40.57  37.00-120.00  103
  4  ω    -92.00  -2.00   1.00    2.00    --  -40.57 125.00 -60.00   90
  5  ω     46.00 166.00   1.00    3.00    --  104.49  15.00  90.00  120
  6  ω     33.00 111.00   1.00    3.00    --  104.49-111.00-180.00   78
  7  ω     32.00 109.00   1.00    3.00    --  104.49 -94.00   0.00   77
  8  ω     32.00 118.00   1.00    3.00    --  104.49 -45.00-150.00   86
  9  ω     75.00 160.00   1.00    3.00    --  104.49  30.00 150.00   85
 10  ω     48.00 109.00   1.00    3.00    --  104.49 -94.00-150.00   61
 11  ω     31.00 110.00   1.00    3.00    --  104.49 -30.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024975000
_diffrn_orient_matrix_UB_12      0.1603444000
_diffrn_orient_matrix_UB_13      0.0150090000
_diffrn_orient_matrix_UB_21      0.0583615000
_diffrn_orient_matrix_UB_22      0.0158366000
_diffrn_orient_matrix_UB_23      -0.0295643000
_diffrn_orient_matrix_UB_31      -0.0416953000
_diffrn_orient_matrix_UB_32      0.0321648000
_diffrn_orient_matrix_UB_33      -0.0600910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25454
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         8266
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0447
_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)+(0.0496P)²+3.0996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7580
_reflns_number_total             8266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0mh00447b9.cif
_cod_data_source_block           ran12cult
_cod_depositor_comments
;Adding full bibliography for 1557668--1557673.cif.

 Adding full bibliography for 1557668--1557673.cif.
;
_cod_original_cell_volume        4581.40(9)
_cod_database_code               1557669
_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.
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
N10 \\sim C33: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
3.a Ternary CH refined with riding coordinates:
 C19(H19), C38(H38), C46(H46), C55(H55), C18(H18), C44(H44), C47(H47), C63(H63)
3.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C34(H34), C40(H40), C41(H41), C42(H42), C43(H43),
 C45(H45), C48(H48), C49(H49), C56(H56), C59(H59), C61(H61), C62(H62), C64(H64),
  C69(H69), C22(H22), C26(H26), C27(H27), C37(H37), C50(H50), C51(H51),
 C54(H54), C58(H58), C60(H60), C65(H65), C66(H66), C67(H67), C68(H68), C70(H70),
  C71(H71), C72(H72)
;
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.708
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
F1 F 0.09876(5) 0.58029(13) 0.26812(5) 0.0372(3) Uani 1 1 d . . . . .
O3 O 0.01109(5) 0.22708(13) 0.01502(5) 0.0232(3) Uani 1 1 d . . . . .
F4 F 0.29398(5) 0.09612(12) -0.17445(5) 0.0340(3) Uani 1 1 d . . . . .
O5 O 0.10408(5) 0.59686(13) -0.09245(5) 0.0237(3) Uani 1 1 d . . . . .
N9 N 0.20280(6) 0.67894(16) -0.07460(6) 0.0218(3) Uani 1 1 d . . . . .
N12 N 0.10010(7) 0.15039(16) 0.07092(6) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.17282(8) 0.73200(18) -0.12943(7) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.11224(8) 0.68224(18) -0.13990(7) 0.0205(3) Uani 1 1 d . . . . .
C16 C 0.16135(8) 0.60238(18) -0.05559(7) 0.0213(3) Uani 1 1 d . . . . .
C17 C 0.04908(8) 0.07504(19) 0.08753(8) 0.0244(4) Uani 1 1 d . . . . .
C19 C 0.17362(7) 0.35588(18) -0.00152(7) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.194766 0.320888 0.038254 0.024 Uiso 1 1 calc R . . . .
C20 C 0.10620(8) 0.51589(17) 0.09036(7) 0.0209(3) Uani 1 1 d . . . . .
C24 C 0.07493(8) 0.23462(18) 0.02950(7) 0.0211(3) Uani 1 1 d . . . . .
C25 C 0.18118(8) 0.29950(19) -0.10964(7) 0.0236(4) Uani 1 1 d . . . . .
H25 H 0.144470 0.353814 -0.122133 0.028 Uiso 1 1 calc R . . . .
C29 C 0.20404(8) 0.28503(17) -0.04879(7) 0.0202(3) Uani 1 1 d . . . . .
C30 C 0.28829(8) 0.13975(19) -0.07378(8) 0.0264(4) Uani 1 1 d . . . . .
H30 H 0.324962 0.084960 -0.061796 0.032 Uiso 1 1 calc R . . . .
C31 C 0.10091(9) 0.55527(19) 0.20943(7) 0.0260(4) Uani 1 1 d . . . . .
C34 C 0.06891(9) 0.7203(2) -0.18900(8) 0.0279(4) Uani 1 1 d . . . . .
H34 H 0.027225 0.686138 -0.194914 0.034 Uiso 1 1 calc R . . . .
C35 C 0.26418(8) 0.15822(18) -0.13304(8) 0.0250(4) Uani 1 1 d . . . . .
C36 C -0.00503(8) 0.12355(18) 0.05268(7) 0.0221(3) Uani 1 1 d . . . . .
C38 C 0.16827(7) 0.52334(18) 0.00173(7) 0.0203(3) Uani 1 1 d . . . . .
H38 H 0.200937 0.565812 0.032941 0.024 Uiso 1 1 calc R . . . .
C40 C 0.09021(10) 0.8110(2) -0.22876(8) 0.0336(4) Uani 1 1 d . . . . .
H40 H 0.062359 0.840692 -0.263250 0.040 Uiso 1 1 calc R . . . .
C41 C -0.06403(8) 0.0742(2) 0.05629(8) 0.0284(4) Uani 1 1 d . . . . .
H41 H -0.100172 0.108490 0.030971 0.034 Uiso 1 1 calc R . . . .
C42 C 0.04969(8) 0.5350(2) 0.10993(8) 0.0258(4) Uani 1 1 d . . . . .
H42 H 0.012217 0.533817 0.081710 0.031 Uiso 1 1 calc R . . . .
C43 C 0.21121(8) 0.23581(19) -0.15225(8) 0.0254(4) Uani 1 1 d . . . . .
H43 H 0.195440 0.245798 -0.193542 0.031 Uiso 1 1 calc R . . . .
C45 C 0.15121(10) 0.8601(2) -0.21985(9) 0.0368(5) Uani 1 1 d . . . . .
H45 H 0.164019 0.921164 -0.248830 0.044 Uiso 1 1 calc R . . . .
C46 C 0.10270(7) 0.34799(18) -0.00292(7) 0.0206(3) Uani 1 1 d . . . . .
H46 H 0.080964 0.350401 -0.045233 0.025 Uiso 1 1 calc R . . . .
C48 C 0.04660(8) 0.5558(2) 0.16965(8) 0.0275(4) Uani 1 1 d . . . . .
H48 H 0.007698 0.569932 0.182517 0.033 Uiso 1 1 calc R . . . .
C49 C 0.16013(8) 0.5125(2) 0.13258(8) 0.0263(4) Uani 1 1 d . . . . .
H49 H 0.199183 0.497202 0.120160 0.032 Uiso 1 1 calc R . . . .
C55 C 0.10484(7) 0.50349(18) 0.02387(7) 0.0199(3) Uani 1 1 d . . . . .
H55 H 0.071697 0.565382 0.001147 0.024 Uiso 1 1 calc R . . . .
C56 C 0.25743(8) 0.20361(19) -0.03187(8) 0.0237(4) Uani 1 1 d . . . . .
H56 H 0.273215 0.191277 0.009310 0.028 Uiso 1 1 calc R . . . .
C59 C 0.04611(10) -0.0299(2) 0.13002(8) 0.0320(4) Uani 1 1 d . . . . .
H59 H 0.082634 -0.066091 0.154153 0.038 Uiso 1 1 calc R . . . .
C61 C 0.19393(9) 0.8232(2) -0.17028(9) 0.0323(4) Uani 1 1 d . . . . .
H61 H 0.235497 0.858122 -0.164273 0.039 Uiso 1 1 calc R . . . .
C62 C -0.01280(10) -0.0795(2) 0.13551(9) 0.0370(5) Uani 1 1 d . . . . .
H62 H -0.016556 -0.150031 0.164643 0.044 Uiso 1 1 calc R . . . .
C64 C -0.06691(10) -0.0287(2) 0.09941(9) 0.0345(4) Uani 1 1 d . . . . .
H64 H -0.106318 -0.065530 0.104611 0.041 Uiso 1 1 calc R . . . .
C69 C 0.15790(8) 0.5312(2) 0.19291(8) 0.0290(4) Uani 1 1 d . . . . .
H69 H 0.194799 0.527358 0.221818 0.035 Uiso 1 1 calc R . . . .
O2 O 0.40855(5) 0.45375(13) 0.14126(5) 0.0241(3) Uani 1 1 d . . . . .
F6 F 0.19363(5) 0.87800(14) 0.19566(5) 0.0385(3) Uani 1 1 d . . . . .
O7 O 0.39958(6) 0.87976(14) -0.09253(6) 0.0292(3) Uani 1 1 d . . . . .
F8 F 0.41836(6) 0.29930(14) -0.21301(5) 0.0409(3) Uani 1 1 d . . . . .
N10 N 0.47027(7) 0.78170(15) -0.02006(6) 0.0227(3) Uani 1 1 d . U . . .
N11 N 0.31449(7) 0.41183(16) 0.08642(6) 0.0231(3) Uani 1 1 d . . . . .
C14 C 0.32338(8) 0.77607(18) 0.08978(8) 0.0229(3) Uani 1 1 d . . . . .
C18 C 0.38790(8) 0.57658(18) 0.04705(7) 0.0209(3) Uani 1 1 d . . . . .
H18 H 0.433038 0.561140 0.045308 0.025 Uiso 1 1 calc R . . . .
C21 C 0.36952(8) 0.50450(18) -0.06768(7) 0.0214(3) Uani 1 1 d . . . . .
C22 C 0.33403(8) 0.52026(19) -0.12376(8) 0.0261(4) Uani 1 1 d . . . . .
H22 H 0.297909 0.578811 -0.128492 0.031 Uiso 1 1 calc R . . . .
C23 C 0.31950(8) 0.33623(19) 0.14042(8) 0.0242(4) Uani 1 1 d . . . . .
C26 C 0.29257(9) 0.7889(2) 0.18705(8) 0.0282(4) Uani 1 1 d . . . . .
H26 H 0.301305 0.774145 0.228895 0.034 Uiso 1 1 calc R . . . .
C27 C 0.35005(9) 0.4526(2) -0.17303(8) 0.0281(4) Uani 1 1 d . . . . .
H27 H 0.325769 0.464779 -0.211440 0.034 Uiso 1 1 calc R . . . .
C28 C 0.36690(8) 0.47547(18) 0.08968(7) 0.0213(3) Uani 1 1 d . . . . .
C32 C 0.50185(8) 0.84766(19) -0.06138(8) 0.0253(4) Uani 1 1 d . . . . .
C33 C 0.41123(8) 0.80491(18) -0.04131(8) 0.0237(3) Uani 1 1 d . U . . .
C37 C 0.42129(9) 0.4172(2) -0.06128(8) 0.0300(4) Uani 1 1 d . . . . .
H37 H 0.445934 0.405439 -0.023011 0.036 Uiso 1 1 calc R . . . .
C39 C 0.45844(8) 0.90737(19) -0.10544(8) 0.0263(4) Uani 1 1 d . . . . .
C44 C 0.35824(8) 0.75166(18) -0.01430(7) 0.0222(3) Uani 1 1 d . . . . .
H44 H 0.318525 0.804313 -0.028278 0.027 Uiso 1 1 calc R . . . .
C47 C 0.34997(8) 0.58516(18) -0.01647(7) 0.0211(3) Uani 1 1 d . . . . .
H47 H 0.305448 0.561969 -0.014718 0.025 Uiso 1 1 calc R . . . .
C50 C 0.26597(8) 0.8337(2) 0.06490(8) 0.0266(4) Uani 1 1 d . . . . .
H50 H 0.256797 0.849186 0.023109 0.032 Uiso 1 1 calc R . . . .
C51 C 0.35554(9) 0.2163(2) 0.25095(8) 0.0327(4) Uani 1 1 d . . . . .
H51 H 0.366577 0.175062 0.289389 0.039 Uiso 1 1 calc R . . . .
C52 C 0.40221(9) 0.3670(2) -0.16481(8) 0.0288(4) Uani 1 1 d . . . . .
C53 C 0.37738(8) 0.36440(19) 0.17406(7) 0.0242(4) Uani 1 1 d . . . . .
C54 C 0.22172(9) 0.8691(2) 0.10018(8) 0.0301(4) Uani 1 1 d . . . . .
H54 H 0.182653 0.909057 0.083186 0.036 Uiso 1 1 calc R . . . .
C57 C 0.23644(9) 0.8445(2) 0.16023(8) 0.0285(4) Uani 1 1 d . . . . .
C58 C 0.27792(9) 0.2436(2) 0.16134(8) 0.0296(4) Uani 1 1 d . . . . .
H58 H 0.238255 0.222388 0.138635 0.036 Uiso 1 1 calc R . . . .
C60 C 0.33597(8) 0.75515(19) 0.15128(8) 0.0259(4) Uani 1 1 d . . . . .
H60 H 0.375156 0.716933 0.168943 0.031 Uiso 1 1 calc R . . . .
C63 C 0.37450(8) 0.74081(18) 0.05472(7) 0.0217(3) Uani 1 1 d . . . . .
H63 H 0.413674 0.793959 0.070309 0.026 Uiso 1 1 calc R . . . .
C65 C 0.39733(9) 0.3068(2) 0.22994(8) 0.0322(4) Uani 1 1 d . . . . .
H65 H 0.437098 0.327859 0.252462 0.039 Uiso 1 1 calc R . . . .
C66 C 0.29755(10) 0.1841(2) 0.21698(8) 0.0336(4) Uani 1 1 d . . . . .
H66 H 0.270772 0.119416 0.232559 0.040 Uiso 1 1 calc R . . . .
C67 C 0.47494(11) 0.9811(2) -0.15346(9) 0.0405(5) Uani 1 1 d . . . . .
H67 H 0.444777 1.023382 -0.183371 0.049 Uiso 1 1 calc R . . . .
C68 C 0.43800(9) 0.3461(2) -0.10985(9) 0.0347(4) Uani 1 1 d . . . . .
H68 H 0.473230 0.284842 -0.105130 0.042 Uiso 1 1 calc R . . . .
C70 C 0.53808(12) 0.9888(3) -0.15481(11) 0.0493(6) Uani 1 1 d . . . . .
H70 H 0.551738 1.037082 -0.186977 0.059 Uiso 1 1 calc R . . . .
C71 C 0.56541(9) 0.8576(2) -0.06323(12) 0.0422(5) Uani 1 1 d . . . . .
H71 H 0.595852 0.817298 -0.033020 0.051 Uiso 1 1 calc R . . . .
C72 C 0.58175(11) 0.9291(2) -0.11133(13) 0.0502(7) Uani 1 1 d . . . . .
H72 H 0.624614 0.937304 -0.114417 0.060 Uiso 1 1 calc R . . . .
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'
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
C24 O3 C36 103.82(13) . . ?
C15 O5 C16 103.45(12) . . ?
C16 N9 C13 104.51(14) . . ?
C24 N12 C17 104.25(14) . . ?
C15 C13 N9 108.84(14) . . ?
C15 C13 C61 120.18(16) . . ?
C61 C13 N9 130.96(16) . . ?
O5 C15 C13 107.77(14) . . ?
O5 C15 C34 128.52(15) . . ?
C13 C15 C34 123.66(16) . . ?
O5 C16 C38 117.58(14) . . ?
N9 C16 O5 115.43(14) . . ?
N9 C16 C38 126.97(15) . . ?
C36 C17 N12 108.18(15) . . ?
C36 C17 C59 119.92(17) . . ?
C59 C17 N12 131.90(17) . . ?
C29 C19 C38 121.11(13) . . ?
C29 C19 C46 121.44(14) . . ?
C46 C19 C38 88.13(12) . . ?
C42 C20 C55 117.42(15) . . ?
C49 C20 C42 118.23(15) . . ?
C49 C20 C55 124.34(15) . . ?
O3 C24 C46 113.44(14) . . ?
N12 C24 O3 115.80(15) . . ?
N12 C24 C46 130.58(15) . . ?
C43 C25 C29 121.20(16) . . ?
C25 C29 C19 122.55(15) . . ?
C56 C29 C19 119.37(14) . . ?
C56 C29 C25 118.07(15) . . ?
C35 C30 C56 118.05(16) . . ?
F1 C31 C69 118.47(16) . . ?
C48 C31 F1 118.80(16) . . ?
C48 C31 C69 122.73(16) . . ?
C40 C34 C15 115.56(17) . . ?
F4 C35 C30 118.55(16) . . ?
F4 C35 C43 118.59(16) . . ?
C43 C35 C30 122.86(16) . . ?
O3 C36 C17 107.94(14) . . ?
O3 C36 C41 127.51(16) . . ?
C41 C36 C17 124.55(17) . . ?
C16 C38 C19 116.94(13) . . ?
C16 C38 C55 112.23(13) . . ?
C55 C38 C19 88.41(12) . . ?
C34 C40 C45 121.85(17) . . ?
C36 C41 C64 115.37(18) . . ?
C48 C42 C20 121.58(16) . . ?
C35 C43 C25 118.24(16) . . ?
C61 C45 C40 122.22(18) . . ?
C19 C46 C55 89.01(12) . . ?
C24 C46 C19 121.03(14) . . ?
C24 C46 C55 117.37(13) . . ?
C31 C48 C42 118.18(16) . . ?
C20 C49 C69 121.01(16) . . ?
C20 C55 C38 116.36(13) . . ?
C20 C55 C46 116.85(13) . . ?
C38 C55 C46 87.48(12) . . ?
C29 C56 C30 121.57(16) . . ?
C62 C59 C17 116.81(18) . . ?
C45 C61 C13 116.51(17) . . ?
C59 C62 C64 122.06(18) . . ?
C41 C64 C62 121.28(18) . . ?
C31 C69 C49 118.20(16) . . ?
C28 O2 C53 103.89(13) . . ?
C33 O7 C39 103.53(14) . . ?
C33 N10 C32 103.84(14) . . ?
C28 N11 C23 104.27(14) . . ?
C50 C14 C60 118.41(16) . . ?
C50 C14 C63 124.07(15) . . ?
C60 C14 C63 117.46(15) . . ?
C28 C18 C47 118.15(14) . . ?
C28 C18 C63 117.90(13) . . ?
C47 C18 C63 88.45(12) . . ?
C22 C21 C47 118.21(15) . . ?
C37 C21 C22 118.68(16) . . ?
C37 C21 C47 123.10(15) . . ?
C27 C22 C21 121.40(16) . . ?
C53 C23 N11 108.49(15) . . ?
C53 C23 C58 120.78(16) . . ?
C58 C23 N11 130.72(17) . . ?
C57 C26 C60 117.98(17) . . ?
C52 C27 C22 118.10(16) . . ?
O2 C28 C18 115.03(14) . . ?
N11 C28 O2 115.80(15) . . ?
N11 C28 C18 129.07(15) . . ?
C39 C32 N10 108.41(15) . . ?
C39 C32 C71 120.94(19) . . ?
C71 C32 N10 130.65(19) . . ?
O7 C33 C44 119.19(15) . . ?
N10 C33 O7 115.84(15) . . ?
N10 C33 C44 124.94(16) . . ?
C21 C37 C68 121.16(16) . . ?
O7 C39 C67 128.98(18) . . ?
C32 C39 O7 108.38(15) . . ?
C32 C39 C67 122.63(18) . . ?
C33 C44 C47 114.52(14) . . ?
C33 C44 C63 112.33(14) . . ?
C63 C44 C47 88.41(12) . . ?
C18 C47 C44 88.97(12) . . ?
C21 C47 C18 121.47(14) . . ?
C21 C47 C44 118.47(14) . . ?
C14 C50 C54 121.18(16) . . ?
C65 C51 C66 121.64(17) . . ?
F8 C52 C27 118.64(16) . . ?
F8 C52 C68 118.95(17) . . ?
C68 C52 C27 122.41(17) . . ?
O2 C53 C23 107.54(14) . . ?
O2 C53 C65 129.08(17) . . ?
C65 C53 C23 123.37(18) . . ?
C57 C54 C50 117.76(17) . . ?
F6 C57 C26 117.90(16) . . ?
F6 C57 C54 118.75(16) . . ?
C54 C57 C26 123.34(17) . . ?
C66 C58 C23 116.43(18) . . ?
C26 C60 C14 121.32(17) . . ?
C14 C63 C18 115.91(14) . . ?
C14 C63 C44 117.15(14) . . ?
C44 C63 C18 88.13(12) . . ?
C53 C65 C51 115.69(18) . . ?
C58 C66 C51 122.07(18) . . ?
C70 C67 C39 115.6(2) . . ?
C52 C68 C37 118.22(17) . . ?
C72 C70 C67 122.3(2) . . ?
C72 C71 C32 116.4(2) . . ?
C70 C72 C71 122.1(2) . . ?
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
F1 C31 1.3648(19) . ?
O3 C24 1.375(2) . ?
O3 C36 1.379(2) . ?
F4 C35 1.3611(19) . ?
O5 C15 1.3798(19) . ?
O5 C16 1.382(2) . ?
N9 C13 1.400(2) . ?
N9 C16 1.283(2) . ?
N12 C17 1.420(2) . ?
N12 C24 1.281(2) . ?
C13 C15 1.381(2) . ?
C13 C61 1.397(3) . ?
C15 C34 1.383(2) . ?
C16 C38 1.486(2) . ?
C17 C36 1.382(3) . ?
C17 C59 1.389(3) . ?
C19 C29 1.509(2) . ?
C19 C38 1.578(2) . ?
C19 C46 1.540(2) . ?
C20 C42 1.388(2) . ?
C20 C49 1.387(2) . ?
C20 C55 1.514(2) . ?
C24 C46 1.480(2) . ?
C25 C29 1.398(2) . ?
C25 C43 1.392(2) . ?
C29 C56 1.390(2) . ?
C30 C35 1.374(3) . ?
C30 C56 1.391(2) . ?
C31 C48 1.364(3) . ?
C31 C69 1.373(3) . ?
C34 C40 1.378(3) . ?
C35 C43 1.371(3) . ?
C36 C41 1.380(2) . ?
C38 C55 1.558(2) . ?
C40 C45 1.387(3) . ?
C41 C64 1.386(3) . ?
C42 C48 1.386(3) . ?
C45 C61 1.381(3) . ?
C46 C55 1.579(2) . ?
C49 C69 1.393(2) . ?
C59 C62 1.389(3) . ?
C62 C64 1.402(3) . ?
O2 C28 1.373(2) . ?
O2 C53 1.374(2) . ?
F6 C57 1.367(2) . ?
O7 C33 1.348(2) . ?
O7 C39 1.385(2) . ?
F8 C52 1.364(2) . ?
N10 C32 1.398(2) . ?
N10 C33 1.313(2) . ?
N11 C23 1.408(2) . ?
N11 C28 1.278(2) . ?
C14 C50 1.392(3) . ?
C14 C60 1.395(2) . ?
C14 C63 1.510(2) . ?
C18 C28 1.483(2) . ?
C18 C47 1.543(2) . ?
C18 C63 1.583(2) . ?
C21 C22 1.385(2) . ?
C21 C37 1.381(3) . ?
C21 C47 1.509(2) . ?
C22 C27 1.383(3) . ?
C23 C53 1.386(3) . ?
C23 C58 1.394(3) . ?
C26 C57 1.374(3) . ?
C26 C60 1.383(3) . ?
C27 C52 1.377(3) . ?
C32 C39 1.377(3) . ?
C32 C71 1.394(3) . ?
C33 C44 1.481(2) . ?
C37 C68 1.390(3) . ?
C39 C67 1.390(3) . ?
C44 C47 1.572(2) . ?
C44 C63 1.555(2) . ?
C50 C54 1.393(2) . ?
C51 C65 1.386(3) . ?
C51 C66 1.398(3) . ?
C52 C68 1.373(3) . ?
C53 C65 1.384(2) . ?
C54 C57 1.371(3) . ?
C58 C66 1.385(3) . ?
C67 C70 1.381(3) . ?
C70 C72 1.372(4) . ?
C71 C72 1.381(4) . ?
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
F1 C31 C48 C42 177.85(16) . . . . ?
F1 C31 C69 C49 -176.97(16) . . . . ?
O3 C24 C46 C19 -168.80(14) . . . . ?
O3 C24 C46 C55 84.42(17) . . . . ?
O3 C36 C41 C64 -178.52(16) . . . . ?
F4 C35 C43 C25 -179.71(15) . . . . ?
O5 C15 C34 C40 178.23(17) . . . . ?
O5 C16 C38 C19 74.63(19) . . . . ?
O5 C16 C38 C55 -25.4(2) . . . . ?
N9 C13 C15 O5 -0.73(19) . . . . ?
N9 C13 C15 C34 176.80(16) . . . . ?
N9 C13 C61 C45 -177.44(18) . . . . ?
N9 C16 C38 C19 -106.94(19) . . . . ?
N9 C16 C38 C55 153.02(16) . . . . ?
N12 C17 C36 O3 -0.11(18) . . . . ?
N12 C17 C36 C41 179.89(16) . . . . ?
N12 C17 C59 C62 178.69(18) . . . . ?
N12 C24 C46 C19 16.3(3) . . . . ?
N12 C24 C46 C55 -90.4(2) . . . . ?
C13 N9 C16 O5 -0.16(19) . . . . ?
C13 N9 C16 C38 -178.62(16) . . . . ?
C13 C15 C34 C40 1.2(3) . . . . ?
C15 O5 C16 N9 -0.27(19) . . . . ?
C15 O5 C16 C38 178.33(14) . . . . ?
C15 C13 C61 C45 0.6(3) . . . . ?
C15 C34 C40 C45 0.1(3) . . . . ?
C16 O5 C15 C13 0.60(17) . . . . ?
C16 O5 C15 C34 -176.77(18) . . . . ?
C16 N9 C13 C15 0.54(19) . . . . ?
C16 N9 C13 C61 178.79(19) . . . . ?
C16 C38 C55 C20 -142.02(15) . . . . ?
C16 C38 C55 C46 99.11(14) . . . . ?
C17 N12 C24 O3 0.14(19) . . . . ?
C17 N12 C24 C46 174.90(17) . . . . ?
C17 C36 C41 C64 1.5(3) . . . . ?
C17 C59 C62 C64 1.1(3) . . . . ?
C19 C29 C56 C30 -178.00(16) . . . . ?
C19 C38 C55 C20 99.41(15) . . . . ?
C19 C38 C55 C46 -19.46(11) . . . . ?
C19 C46 C55 C20 -98.46(15) . . . . ?
C19 C46 C55 C38 19.96(12) . . . . ?
C20 C42 C48 C31 -0.8(3) . . . . ?
C20 C49 C69 C31 -1.0(3) . . . . ?
C24 O3 C36 C17 0.18(17) . . . . ?
C24 O3 C36 C41 -179.82(17) . . . . ?
C24 N12 C17 C36 -0.01(18) . . . . ?
C24 N12 C17 C59 -179.64(19) . . . . ?
C24 C46 C55 C20 26.4(2) . . . . ?
C24 C46 C55 C38 144.82(14) . . . . ?
C25 C29 C56 C30 1.1(3) . . . . ?
C29 C19 C38 C16 31.9(2) . . . . ?
C29 C19 C38 C55 146.11(14) . . . . ?
C29 C19 C46 C24 92.70(19) . . . . ?
C29 C19 C46 C55 -145.55(15) . . . . ?
C29 C25 C43 C35 -0.1(3) . . . . ?
C30 C35 C43 C25 0.7(3) . . . . ?
C34 C40 C45 C61 -1.1(3) . . . . ?
C35 C30 C56 C29 -0.6(3) . . . . ?
C36 O3 C24 N12 -0.21(18) . . . . ?
C36 O3 C24 C46 -175.88(13) . . . . ?
C36 C17 C59 C62 -0.9(3) . . . . ?
C36 C41 C64 C62 -1.2(3) . . . . ?
C38 C19 C29 C25 -61.4(2) . . . . ?
C38 C19 C29 C56 117.59(17) . . . . ?
C38 C19 C46 C24 -141.43(15) . . . . ?
C38 C19 C46 C55 -19.68(11) . . . . ?
C40 C45 C61 C13 0.7(3) . . . . ?
C42 C20 C49 C69 -1.5(3) . . . . ?
C42 C20 C55 C38 164.01(15) . . . . ?
C42 C20 C55 C46 -94.69(18) . . . . ?
C43 C25 C29 C19 178.32(16) . . . . ?
C43 C25 C29 C56 -0.7(3) . . . . ?
C46 C19 C29 C25 47.5(2) . . . . ?
C46 C19 C29 C56 -133.49(17) . . . . ?
C46 C19 C38 C16 -94.28(15) . . . . ?
C46 C19 C38 C55 19.96(11) . . . . ?
C48 C31 C69 C49 2.8(3) . . . . ?
C49 C20 C42 C48 2.4(3) . . . . ?
C49 C20 C55 C38 -14.5(2) . . . . ?
C49 C20 C55 C46 86.8(2) . . . . ?
C55 C20 C42 C48 -176.19(16) . . . . ?
C55 C20 C49 C69 177.01(17) . . . . ?
C56 C30 C35 F4 -179.96(15) . . . . ?
C56 C30 C35 C43 -0.3(3) . . . . ?
C59 C17 C36 O3 179.57(15) . . . . ?
C59 C17 C36 C41 -0.4(3) . . . . ?
C59 C62 C64 C41 -0.1(3) . . . . ?
C61 C13 C15 O5 -179.20(16) . . . . ?
C61 C13 C15 C34 -1.7(3) . . . . ?
C69 C31 C48 C42 -1.9(3) . . . . ?
O2 C53 C65 C51 -178.30(17) . . . . ?
O7 C33 C44 C47 110.94(17) . . . . ?
O7 C33 C44 C63 -150.18(15) . . . . ?
O7 C39 C67 C70 -178.77(18) . . . . ?
F8 C52 C68 C37 179.29(18) . . . . ?
N10 C32 C39 O7 -0.09(19) . . . . ?
N10 C32 C39 C67 -179.94(17) . . . . ?
N10 C32 C71 C72 178.91(18) . . . . ?
N10 C33 C44 C47 -67.0(2) . . . . ?
N10 C33 C44 C63 31.8(2) . . . . ?
N11 C23 C53 O2 -1.14(19) . . . . ?
N11 C23 C53 C65 179.89(17) . . . . ?
N11 C23 C58 C66 179.11(18) . . . . ?
C14 C50 C54 C57 -0.4(3) . . . . ?
C21 C22 C27 C52 0.8(3) . . . . ?
C21 C37 C68 C52 1.1(3) . . . . ?
C22 C21 C37 C68 0.1(3) . . . . ?
C22 C21 C47 C18 -178.38(16) . . . . ?
C22 C21 C47 C44 -70.4(2) . . . . ?
C22 C27 C52 F8 179.78(16) . . . . ?
C22 C27 C52 C68 0.6(3) . . . . ?
C23 N11 C28 O2 -0.76(19) . . . . ?
C23 N11 C28 C18 -176.78(16) . . . . ?
C23 C53 C65 C51 0.4(3) . . . . ?
C23 C58 C66 C51 0.8(3) . . . . ?
C27 C52 C68 C37 -1.5(3) . . . . ?
C28 O2 C53 C23 0.67(17) . . . . ?
C28 O2 C53 C65 179.56(18) . . . . ?
C28 N11 C23 C53 1.15(18) . . . . ?
C28 N11 C23 C58 -177.43(19) . . . . ?
C28 C18 C47 C21 -97.33(19) . . . . ?
C28 C18 C47 C44 139.44(15) . . . . ?
C28 C18 C63 C14 -20.4(2) . . . . ?
C28 C18 C63 C44 -139.87(15) . . . . ?
C32 N10 C33 O7 -0.1(2) . . . . ?
C32 N10 C33 C44 177.91(16) . . . . ?
C32 C39 C67 C70 1.1(3) . . . . ?
C32 C71 C72 C70 0.7(3) . . . . ?
C33 O7 C39 C32 0.02(18) . . . . ?
C33 O7 C39 C67 179.86(19) . . . . ?
C33 N10 C32 C39 0.12(19) . . . . ?
C33 N10 C32 C71 -179.19(19) . . . . ?
C33 C44 C47 C18 95.20(15) . . . . ?
C33 C44 C47 C21 -30.5(2) . . . . ?
C33 C44 C63 C14 143.93(15) . . . . ?
C33 C44 C63 C18 -97.73(15) . . . . ?
C37 C21 C22 C27 -1.1(3) . . . . ?
C37 C21 C47 C18 1.0(3) . . . . ?
C37 C21 C47 C44 108.91(19) . . . . ?
C39 O7 C33 N10 0.1(2) . . . . ?
C39 O7 C33 C44 -178.08(15) . . . . ?
C39 C32 C71 C72 -0.3(3) . . . . ?
C39 C67 C70 C72 -0.7(3) . . . . ?
C47 C18 C28 O2 168.50(14) . . . . ?
C47 C18 C28 N11 -15.5(3) . . . . ?
C47 C18 C63 C14 100.89(15) . . . . ?
C47 C18 C63 C44 -18.57(12) . . . . ?
C47 C21 C22 C27 178.31(16) . . . . ?
C47 C21 C37 C68 -179.24(18) . . . . ?
C47 C44 C63 C14 -100.12(15) . . . . ?
C47 C44 C63 C18 18.21(12) . . . . ?
C50 C14 C60 C26 0.7(3) . . . . ?
C50 C14 C63 C18 -110.25(19) . . . . ?
C50 C14 C63 C44 -8.2(2) . . . . ?
C50 C54 C57 F6 -179.78(17) . . . . ?
C50 C54 C57 C26 0.9(3) . . . . ?
C53 O2 C28 N11 0.08(19) . . . . ?
C53 O2 C28 C18 176.66(14) . . . . ?
C53 C23 C58 C66 0.7(3) . . . . ?
C57 C26 C60 C14 -0.2(3) . . . . ?
C58 C23 C53 O2 177.61(15) . . . . ?
C58 C23 C53 C65 -1.4(3) . . . . ?
C60 C14 C50 C54 -0.4(3) . . . . ?
C60 C14 C63 C18 72.7(2) . . . . ?
C60 C14 C63 C44 174.77(15) . . . . ?
C60 C26 C57 F6 -179.91(16) . . . . ?
C60 C26 C57 C54 -0.6(3) . . . . ?
C63 C14 C50 C54 -177.38(17) . . . . ?
C63 C14 C60 C26 177.92(16) . . . . ?
C63 C18 C28 O2 -87.11(18) . . . . ?
C63 C18 C28 N11 88.9(2) . . . . ?
C63 C18 C47 C21 141.58(15) . . . . ?
C63 C18 C47 C44 18.35(12) . . . . ?
C63 C44 C47 C18 -18.70(12) . . . . ?
C63 C44 C47 C21 -144.44(15) . . . . ?
C65 C51 C66 C58 -1.8(3) . . . . ?
C66 C51 C65 C53 1.1(3) . . . . ?
C67 C70 C72 C71 -0.1(3) . . . . ?
C71 C32 C39 O7 179.30(16) . . . . ?
C71 C32 C39 C67 -0.6(3) . . . . ?
