#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:27:30 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261739 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/02/7060203.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_7060203
loop_
_publ_author_name
'Miura, Youhei'
'Kobayashi, Kotaro'
'Yoshioka, Naoki'
_publ_section_title
;
 V-shaped fluorophores with a 1-methyl-4,5-bis(arylethynyl)imidazole
 skeleton displaying solid-state fluorescence, acid responsiveness, and
 remarkable fluorescence solvatochromism
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              898
_journal_page_last               905
_journal_paper_doi               10.1039/D0NJ05323F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_sum            'C50 H35 F9 N4 O10'
_chemical_formula_weight         1022.82
_chemical_melting_point          407.0(10)
_chemical_name_common            NMeOMeCHO
_chemical_name_systematic
'4-(4-methoxyphenylethynyl)-5-(4-formylphenylethynyl)-1-methylimidazolium trifluoroacetate'
_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_update_record
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                91.829(2)
_cell_angle_beta                 115.533(2)
_cell_angle_gamma                92.604(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8968(8)
_cell_length_b                   14.4328(9)
_cell_length_c                   14.7466(10)
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      21.0157
_cell_measurement_theta_min      2.2408
_cell_volume                     2470.2(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21127
_diffrn_reflns_theta_full        23.34
_diffrn_reflns_theta_max         23.34
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light yellow-colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.704
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         6930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1972
_refine_ls_wR_factor_ref         0.2456
_reflns_number_gt                3593
_reflns_number_total             6930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05323f2.cif
_cod_data_source_block           X191029KK_NMeOMeCHO_TFA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '406-408' was changed to
'407.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7060201--7060208.cif.
;
_cod_database_code               7060203
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O8 0.0290(3) 0.0415(3) 0.2947(3) 0.0838(10) Uani d . . . 1 . .
N N4 0.9739(3) 0.0926(2) 0.4349(3) 0.0636(10) Uani d . . . 1 . .
H H4 0.9918 0.077 0.3869 0.076 Uiso calc U . R 1 . .
N N3 0.9888(3) 0.1441(2) 0.5790(3) 0.0649(10) Uani d . . . 1 . .
O O5 0.2605(3) 0.5119(3) 0.2781(3) 0.0941(12) Uani d . . . 1 . .
O O4 0.2832(3) 0.2313(3) 0.6725(3) 0.0969(12) Uani d . . . 1 . .
N N1 0.5765(3) 0.6538(2) 0.5678(3) 0.0655(10) Uani d . . . 1 . .
O O2 1.3831(3) 0.7306(3) 0.6616(3) 0.1070(13) Uani d . . . 1 . .
N N2 0.4457(3) 0.5928(2) 0.4265(3) 0.0697(11) Uani d . . . 1 . .
H H2 0.3795 0.5741 0.3796 0.084 Uiso calc U . R 1 . .
O O3 0.2800(4) -0.1261(3) -0.0480(3) 0.1052(13) Uani d . . . 1 . .
O O7 0.1948(4) 0.1221(3) 0.3873(3) 0.1108(14) Uani d . . . 1 . .
O O1 0.6766(4) 0.3724(3) -0.0348(3) 0.1123(13) Uani d . . . 1 . .
F F1 0.1805(4) 0.6217(3) 0.3682(4) 0.1677(19) Uani d . . . 1 . .
O O6 0.0801(4) 0.4540(3) 0.1728(3) 0.1224(16) Uani d . . . 1 . .
F F5 0.1310(4) -0.0296(3) 0.1892(3) 0.1649(19) Uani d . . . 1 . .
C C40 0.4713(4) 0.2100(3) 0.6860(4) 0.0612(12) Uani d . . . 1 . .
F F4 0.2790(4) 0.0548(3) 0.2683(4) 0.1652(18) Uani d . . . 1 . .
C C37 0.6336(4) 0.1594(3) 0.6217(4) 0.0619(12) Uani d . . . 1 . .
C C2 0.5510(4) 0.5829(3) 0.4237(4) 0.0654(13) Uani d . . . 1 . .
C C25 0.8658(4) 0.0827(3) 0.4306(4) 0.0601(12) Uani d . . . 1 . .
F F3 0.0159(4) 0.5494(3) 0.2970(4) 0.171(2) Uani d . . . 1 . .
C C24 0.8750(4) 0.1158(3) 0.5226(4) 0.0606(12) Uani d . . . 1 . .
C C23 1.0453(4) 0.1291(3) 0.5225(4) 0.0633(12) Uani d . . . 1 . .
H H23 1.1236 0.1428 0.5429 0.076 Uiso calc U . R 1 . .
C C29 0.5801(4) -0.0191(3) 0.1901(4) 0.0655(13) Uani d . . . 1 . .
C C41 0.5866(4) 0.2272(3) 0.7474(4) 0.0684(13) Uani d . . . 1 . .
H H41 0.6099 0.256 0.811 0.082 Uiso calc U . R 1 . .
C C28 0.6832(5) 0.0159(3) 0.2735(4) 0.0664(13) Uani d . . . 1 . .
C C3 0.6336(4) 0.6216(3) 0.5123(4) 0.0649(13) Uani d . . . 1 . .
C C36 0.7187(4) 0.1381(3) 0.5858(4) 0.0679(13) Uani d . . . 1 . .
C C42 0.6681(4) 0.2025(3) 0.7160(4) 0.0712(13) Uani d . . . 1 . .
H H42 0.746 0.2147 0.7581 0.085 Uiso calc U . R 1 . .
C C18 1.2088(4) 0.7109(3) 0.6789(4) 0.0659(13) Uani d . . . 1 . .
C C1 0.4642(4) 0.6356(3) 0.5130(4) 0.0716(14) Uani d . . . 1 . .
H H1 0.4072 0.6507 0.5326 0.086 Uiso calc U . R 1 . .
F F6 0.1357(5) 0.1142(4) 0.1677(4) 0.215(3) Uani d . . . 1 . .
C C35 0.7892(4) 0.1261(3) 0.5561(4) 0.0674(13) Uani d . . . 1 . .
C C32 0.3748(5) -0.0880(4) 0.0322(4) 0.0735(14) Uani d . . . 1 . .
C C38 0.5176(4) 0.1395(3) 0.5607(4) 0.0726(14) Uani d . . . 1 . .
H H38 0.4942 0.1094 0.4976 0.087 Uiso calc U . R 1 . .
C C27 0.7675(5) 0.0455(3) 0.3449(4) 0.0669(13) Uani d . . . 1 . .
C C39 0.4364(4) 0.1642(3) 0.5932(4) 0.0728(14) Uani d . . . 1 . .
H H39 0.3585 0.1499 0.5526 0.087 Uiso calc U . R 1 . .
C C48 0.1283(5) 0.0756(4) 0.3135(4) 0.0761(14) Uani d . . . 1 . .
C C15 0.9766(4) 0.6641(3) 0.6135(4) 0.0685(13) Uani d . . . 1 . .
C C14 0.8553(5) 0.6451(3) 0.5777(4) 0.0726(14) Uani d . . . 1 . .
C C17 1.1441(5) 0.6680(4) 0.5849(4) 0.0839(16) Uani d . . . 1 . .
H H17 1.1794 0.6552 0.5431 0.101 Uiso calc U . R 1 . .
C C34 0.4749(4) 0.0065(3) 0.1827(4) 0.0750(14) Uani d . . . 1 . .
H H34 0.4727 0.0474 0.2318 0.09 Uiso calc U . R 1 . .
C C19 1.1565(4) 0.7281(3) 0.7398(4) 0.0728(14) Uani d . . . 1 . .
H H19 1.1997 0.7554 0.8041 0.087 Uiso calc U . R 1 . .
C C33 0.3736(5) -0.0274(4) 0.1044(4) 0.0776(14) Uani d . . . 1 . .
H H33 0.3038 -0.0088 0.1006 0.093 Uiso calc U . R 1 . .
C C13 0.7534(5) 0.6326(3) 0.5472(4) 0.0718(14) Uani d . . . 1 . .
C C7 0.6022(5) 0.4778(3) 0.1924(4) 0.0742(14) Uani d . . . 1 . .
C C30 0.5808(5) -0.0800(3) 0.1153(4) 0.0712(13) Uani d . . . 1 . .
H H30 0.6506 -0.0976 0.1181 0.085 Uiso calc U . R 1 . .
C C5 0.5618(4) 0.5433(3) 0.3402(4) 0.0726(14) Uani d . . . 1 . .
F F2 0.0646(5) 0.6445(4) 0.2189(4) 0.205(3) Uani d . . . 1 . .
C C44 0.3858(5) 0.2416(3) 0.7201(4) 0.0750(14) Uani d . . . 1 . .
H H44 0.4138 0.2719 0.7835 0.09 Uiso calc U . R 1 . .
C C6 0.5777(4) 0.5129(3) 0.2723(4) 0.0749(14) Uani d . . . 1 . .
C C10 0.6572(6) 0.4097(4) 0.0412(4) 0.0831(15) Uani d . . . 1 . .
C C22 1.3301(4) 0.7398(3) 0.7120(4) 0.0813(15) Uani d . . . 1 . .
H H22 1.37 0.7672 0.7767 0.098 Uiso calc U . R 1 . .
C C20 1.0406(5) 0.7057(3) 0.7079(4) 0.0752(14) Uani d . . . 1 . .
H H20 1.0058 0.7187 0.7501 0.09 Uiso calc U . R 1 . .
C C31 0.4803(5) -0.1141(3) 0.0380(4) 0.0768(15) Uani d . . . 1 . .
H H31 0.4819 -0.1551 -0.0112 0.092 Uiso calc U . R 1 . .
C C46 0.1558(6) 0.5070(4) 0.2417(5) 0.0924(17) Uani d . . . 1 . .
C C16 1.0297(5) 0.6439(3) 0.5517(4) 0.0802(15) Uani d . . . 1 . .
H H16 0.9877 0.6144 0.4883 0.096 Uiso calc U . R 1 . .
C C8 0.5238(5) 0.4188(3) 0.1137(4) 0.0809(15) Uani d . . . 1 . .
H H8 0.4519 0.4026 0.1111 0.097 Uiso calc U . R 1 . .
C C12 0.7063(5) 0.5028(4) 0.1917(4) 0.0902(16) Uani d . . . 1 . .
H H12 0.759 0.5434 0.2427 0.108 Uiso calc U . R 1 . .
C C9 0.5521(6) 0.3847(4) 0.0406(4) 0.0880(16) Uani d . . . 1 . .
H H9 0.4999 0.344 -0.0106 0.106 Uiso calc U . R 1 . .
C C47 0.1665(6) 0.0531(5) 0.2344(6) 0.1045(19) Uani d . . . 1 . .
O O9 0.1814(8) 0.3553(5) 0.0881(5) 0.210(4) Uani d . . . 1 . .
C C26 1.0407(5) 0.1822(4) 0.6839(4) 0.0894(17) Uani d . . . 1 . .
H H26A 1.0022 0.236 0.6891 0.134 Uiso calc U . R 1 . .
H H26B 1.1209 0.1992 0.7045 0.134 Uiso calc U . R 1 . .
H H26C 1.0331 0.1361 0.7265 0.134 Uiso calc U . R 1 . .
C C4 0.6335(5) 0.7006(4) 0.6677(4) 0.0933(17) Uani d . . . 1 . .
H H4A 0.577 0.7272 0.685 0.14 Uiso calc U . R 1 . .
H H4B 0.6873 0.7489 0.6679 0.14 Uiso calc U . R 1 . .
H H4C 0.6737 0.6566 0.7161 0.14 Uiso calc U . R 1 . .
C C45 0.1032(7) 0.5772(5) 0.2807(6) 0.112(2) Uani d . . . 1 . .
C C11 0.7339(5) 0.4689(4) 0.1165(5) 0.0911(17) Uani d . . . 1 . .
H H11 0.8046 0.4864 0.1173 0.109 Uiso calc U . R 1 . .
F F8 0.2789(7) 0.2096(5) 0.0523(6) 0.240(3) Uani d . . . 1 . .
F F7 0.2083(7) 0.2797(5) -0.0780(5) 0.251(4) Uani d . . . 1 . .
C C50 0.1364(11) 0.2976(8) 0.0365(9) 0.153(3) Uani d . . . 1 . .
F F9 0.1242(8) 0.1626(5) -0.0601(6) 0.278(4) Uani d . . . 1 . .
C C49 0.1809(15) 0.2391(8) -0.0164(9) 0.183(5) Uani d . . . 1 . .
C C43 0.1715(6) -0.1003(6) -0.0570(6) 0.153(3) Uani d . . . 1 . .
H H43A 0.1628 -0.1159 0.0022 0.229 Uiso calc U . R 1 . .
H H43B 0.1115 -0.1329 -0.115 0.229 Uiso calc U . R 1 . .
H H43C 0.1665 -0.0346 -0.0645 0.229 Uiso calc U . R 1 . .
O O10 0.0311(9) 0.2694(6) 0.0113(8) 0.263(5) Uani d . . . 1 . .
C C21 0.7865(7) 0.3937(6) -0.0347(6) 0.160(3) Uani d . . . 1 . .
H H21A 0.7938 0.4584 -0.0457 0.24 Uiso calc U . R 1 . .
H H21B 0.7925 0.3568 -0.0873 0.24 Uiso calc U . R 1 . .
H H21C 0.8467 0.3802 0.0291 0.24 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 N4 C25 . . 109.6(4) ?
C23 N4 H4 . . 125.2 ?
C25 N4 H4 . . 125.2 ?
C23 N3 C24 . . 108.0(4) ?
C23 N3 C26 . . 125.7(4) ?
C24 N3 C26 . . 126.2(4) ?
C1 N1 C3 . . 108.1(4) ?
C1 N1 C4 . . 127.4(4) ?
C3 N1 C4 . . 124.5(4) ?
C1 N2 C2 . . 108.8(4) ?
C1 N2 H2 . . 125.6 ?
C2 N2 H2 . . 125.6 ?
C32 O3 C43 . . 117.2(4) ?
C10 O1 C21 . . 118.1(5) ?
C41 C40 C39 . . 119.8(4) ?
C41 C40 C44 . . 119.5(5) ?
C39 C40 C44 . . 120.7(5) ?
C42 C37 C38 . . 119.8(4) ?
C42 C37 C36 . . 119.8(4) ?
C38 C37 C36 . . 120.4(4) ?
C3 C2 C5 . . 129.7(5) ?
C3 C2 N2 . . 106.8(4) ?
C5 C2 N2 . . 123.4(5) ?
N4 C25 C24 . . 106.5(4) ?
N4 C25 C27 . . 123.9(4) ?
C24 C25 C27 . . 129.5(4) ?
C25 C24 N3 . . 106.4(4) ?
C25 C24 C35 . . 129.9(5) ?
N3 C24 C35 . . 123.6(4) ?
N4 C23 N3 . . 109.5(4) ?
N4 C23 H23 . . 125.3 ?
N3 C23 H23 . . 125.3 ?
C34 C29 C30 . . 118.1(5) ?
C34 C29 C28 . . 119.7(4) ?
C30 C29 C28 . . 122.2(4) ?
C40 C41 C42 . . 120.9(5) ?
C40 C41 H41 . . 119.5 ?
C42 C41 H41 . . 119.5 ?
C27 C28 C29 . . 178.1(5) ?
C2 C3 N1 . . 106.6(4) ?
C2 C3 C13 . . 130.5(5) ?
N1 C3 C13 . . 122.9(5) ?
C35 C36 C37 . . 176.2(5) ?
C41 C42 C37 . . 119.6(5) ?
C41 C42 H42 . . 120.2 ?
C37 C42 H42 . . 120.2 ?
C19 C18 C17 . . 118.5(5) ?
C19 C18 C22 . . 120.2(5) ?
C17 C18 C22 . . 121.2(5) ?
N2 C1 N1 . . 109.7(4) ?
N2 C1 H1 . . 125.2 ?
N1 C1 H1 . . 125.2 ?
C36 C35 C24 . . 177.5(5) ?
O3 C32 C33 . . 125.2(5) ?
O3 C32 C31 . . 115.6(5) ?
C33 C32 C31 . . 119.2(5) ?
C37 C38 C39 . . 120.2(5) ?
C37 C38 H38 . . 119.9 ?
C39 C38 H38 . . 119.9 ?
C28 C27 C25 . . 178.2(5) ?
C40 C39 C38 . . 119.8(5) ?
C40 C39 H39 . . 120.1 ?
C38 C39 H39 . . 120.1 ?
O7 C48 O8 . . 128.3(5) ?
O7 C48 C47 . . 117.6(6) ?
O8 C48 C47 . . 114.1(6) ?
C20 C15 C16 . . 119.7(5) ?
C20 C15 C14 . . 120.2(5) ?
C16 C15 C14 . . 120.1(5) ?
C13 C14 C15 . . 177.6(5) ?
C16 C17 C18 . . 121.8(5) ?
C16 C17 H17 . . 119.1 ?
C18 C17 H17 . . 119.1 ?
C33 C34 C29 . . 121.3(5) ?
C33 C34 H34 . . 119.4 ?
C29 C34 H34 . . 119.4 ?
C18 C19 C20 . . 121.1(5) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C32 C33 C34 . . 120.3(5) ?
C32 C33 H33 . . 119.8 ?
C34 C33 H33 . . 119.8 ?
C14 C13 C3 . . 177.8(5) ?
C12 C7 C8 . . 118.1(5) ?
C12 C7 C6 . . 119.6(5) ?
C8 C7 C6 . . 122.3(5) ?
C31 C30 C29 . . 120.6(5) ?
C31 C30 H30 . . 119.7 ?
C29 C30 H30 . . 119.7 ?
C6 C5 C2 . . 175.7(6) ?
O4 C44 C40 . . 125.3(5) ?
O4 C44 H44 . . 117.4 ?
C40 C44 H44 . . 117.4 ?
C5 C6 C7 . . 177.5(6) ?
O1 C10 C11 . . 124.1(6) ?
O1 C10 C9 . . 116.4(6) ?
C11 C10 C9 . . 119.5(5) ?
O2 C22 C18 . . 125.0(5) ?
O2 C22 H22 . . 117.5 ?
C18 C22 H22 . . 117.5 ?
C15 C20 C19 . . 119.8(5) ?
C15 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C30 C31 C32 . . 120.5(5) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
O5 C46 O6 . . 132.3(6) ?
O5 C46 C45 . . 116.2(7) ?
O6 C46 C45 . . 111.5(6) ?
C17 C16 C15 . . 119.1(5) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C9 C8 C7 . . 120.3(5) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C7 C12 C11 . . 121.3(5) ?
C7 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C8 C9 C10 . . 121.0(5) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
F6 C47 F5 . . 108.9(7) ?
F6 C47 F4 . . 104.3(6) ?
F5 C47 F4 . . 103.9(5) ?
F6 C47 C48 . . 110.6(5) ?
F5 C47 C48 . . 115.0(6) ?
F4 C47 C48 . . 113.4(6) ?
N3 C26 H26A . . 109.5 ?
N3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
F3 C45 F2 . . 104.2(7) ?
F3 C45 F1 . . 106.0(6) ?
F2 C45 F1 . . 103.8(6) ?
F3 C45 C46 . . 117.5(6) ?
F2 C45 C46 . . 111.7(6) ?
F1 C45 C46 . . 112.4(7) ?
C10 C11 C12 . . 119.8(6) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
O9 C50 O10 . . 124.9(13) ?
O9 C50 C49 . . 126.8(15) ?
O10 C50 C49 . . 108.2(13) ?
F7 C49 F9 . . 107.7(10) ?
F7 C49 F8 . . 105.2(14) ?
F9 C49 F8 . . 102.2(9) ?
F7 C49 C50 . . 114.6(10) ?
F9 C49 C50 . . 118.8(15) ?
F8 C49 C50 . . 106.6(10) ?
O3 C43 H43A . . 109.5 ?
O3 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
O3 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
O1 C21 H21A . . 109.5 ?
O1 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O1 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O8 C48 . 1.260(6) ?
N4 C23 . 1.296(5) ?
N4 C25 . 1.368(5) ?
N4 H4 . 0.86 ?
N3 C23 . 1.343(5) ?
N3 C24 . 1.373(5) ?
N3 C26 . 1.470(6) ?
O5 C46 . 1.217(7) ?
O4 C44 . 1.200(6) ?
N1 C1 . 1.328(6) ?
N1 C3 . 1.399(5) ?
N1 C4 . 1.457(6) ?
O2 C22 . 1.215(6) ?
N2 C1 . 1.319(6) ?
N2 C2 . 1.389(5) ?
N2 H2 . 0.86 ?
O3 C32 . 1.358(6) ?
O3 C43 . 1.416(7) ?
O7 C48 . 1.210(6) ?
O1 C10 . 1.351(6) ?
O1 C21 . 1.435(7) ?
F1 C45 . 1.361(8) ?
O6 C46 . 1.264(7) ?
F5 C47 . 1.310(7) ?
C40 C41 . 1.373(6) ?
C40 C39 . 1.377(6) ?
C40 C44 . 1.477(6) ?
F4 C47 . 1.314(7) ?
C37 C42 . 1.381(6) ?
C37 C38 . 1.383(6) ?
C37 C36 . 1.450(6) ?
C2 C3 . 1.361(6) ?
C2 C5 . 1.405(7) ?
C25 C24 . 1.378(6) ?
C25 C27 . 1.417(7) ?
F3 C45 . 1.298(7) ?
C24 C35 . 1.404(6) ?
C23 H23 . 0.93 ?
C29 C34 . 1.382(6) ?
C29 C30 . 1.392(6) ?
C29 C28 . 1.423(7) ?
C41 C42 . 1.374(6) ?
C41 H41 . 0.93 ?
C28 C27 . 1.189(6) ?
C3 C13 . 1.401(7) ?
C36 C35 . 1.183(6) ?
C42 H42 . 0.93 ?
C18 C19 . 1.358(6) ?
C18 C17 . 1.379(7) ?
C18 C22 . 1.459(7) ?
C1 H1 . 0.93 ?
F6 C47 . 1.286(7) ?
C32 C33 . 1.362(6) ?
C32 C31 . 1.395(7) ?
C38 C39 . 1.382(6) ?
C38 H38 . 0.93 ?
C39 H39 . 0.93 ?
C48 C47 . 1.482(8) ?
C15 C20 . 1.374(6) ?
C15 C16 . 1.387(6) ?
C15 C14 . 1.428(7) ?
C14 C13 . 1.195(6) ?
C17 C16 . 1.363(7) ?
C17 H17 . 0.93 ?
C34 C33 . 1.373(6) ?
C34 H34 . 0.93 ?
C19 C20 . 1.380(6) ?
C19 H19 . 0.93 ?
C33 H33 . 0.93 ?
C7 C12 . 1.379(7) ?
C7 C8 . 1.393(7) ?
C7 C6 . 1.429(7) ?
C30 C31 . 1.362(6) ?
C30 H30 . 0.93 ?
C5 C6 . 1.181(6) ?
F2 C45 . 1.316(7) ?
C44 H44 . 0.93 ?
C10 C11 . 1.362(7) ?
C10 C9 . 1.382(7) ?
C22 H22 . 0.93 ?
C20 H20 . 0.93 ?
C31 H31 . 0.93 ?
C46 C45 . 1.476(8) ?
C16 H16 . 0.93 ?
C8 C9 . 1.364(7) ?
C8 H8 . 0.93 ?
C12 C11 . 1.386(7) ?
C12 H12 . 0.93 ?
C9 H9 . 0.93 ?
O9 C50 . 1.070(12) ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C11 H11 . 0.93 ?
F8 C49 . 1.333(13) ?
F7 C49 . 1.259(12) ?
C50 O10 . 1.286(12) ?
C50 C49 . 1.427(13) ?
F9 C49 . 1.283(13) ?
C43 H43A . 0.96 ?
C43 H43B . 0.96 ?
C43 H43C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
