#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:53:33 +0300 (Thu, 05 May 2022) $
#$Revision: 275053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158632.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_7158632
loop_
_publ_author_name
'Fang, Zheng'
'Teng, Yun'
'Yang, Huilin'
'Li, Rongxing'
'Li, Qiuhong'
'You, Yi'
'Weng, Zhiqiang'
_publ_section_title
;
 Synthesis of 4-trifluoromethyl pyridazines via annulation of
 pyridinium ylides with trifluoroacetyl diazoester.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3564
_journal_page_last               3569
_journal_paper_doi               10.1039/d2ob00483f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 F3 N2 O4'
_chemical_formula_sum            'C22 H15 F3 N2 O4'
_chemical_formula_weight         428.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-11 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.751(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.4017(14)
_cell_length_b                   10.6516(5)
_cell_length_c                   14.9143(8)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.763
_cell_measurement_theta_min      2.353
_cell_volume                     4029.0(4)
_computing_cell_refinement       lb20201022
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            63913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.074
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7127
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0376
_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)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6492
_reflns_number_total             7127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00483f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7158630--7158632.cif.'
_cod_database_code               7158632
_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   0.988
_shelx_estimated_absorpt_t_min   0.977
_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.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C34(H34), C35(H35), C41(H41), C42(H42), C45(H45),
 C46(H46), C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54),
  C56(H56), C57(H57), C58(H58), C60(H60), C61(H61)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
F1 F 0.43540(9) 0.41883(19) 0.33519(15) 0.0436(5) Uani 1 1 d . . . . .
F4 F 0.02505(9) 1.5289(2) 0.14532(15) 0.0443(5) Uani 1 1 d . . . . .
F5 F -0.03270(8) 1.4842(2) 0.19485(17) 0.0481(5) Uani 1 1 d . . . . .
F2 F 0.49188(8) 0.4451(2) 0.27871(17) 0.0484(6) Uani 1 1 d . . . . .
F6 F 0.02816(9) 1.61792(19) 0.27705(17) 0.0470(5) Uani 1 1 d . . . . .
F3 F 0.42690(9) 0.32062(17) 0.20271(17) 0.0478(5) Uani 1 1 d . . . . .
O4 O 0.13953(12) 1.5629(2) 0.2740(2) 0.0448(7) Uani 1 1 d . . . . .
O6 O 0.21029(10) 1.3163(2) 0.3674(2) 0.0458(7) Uani 1 1 d . . . . .
O2 O 0.31960(11) 0.3934(2) 0.2052(2) 0.0440(6) Uani 1 1 d . . . . .
O1 O 0.25323(10) 0.6500(2) 0.1148(2) 0.0431(6) Uani 1 1 d . . . . .
O3 O 0.51444(10) 0.6486(3) 0.1572(2) 0.0488(7) Uani 1 1 d . . . . .
O5 O -0.04753(10) 1.2711(3) 0.3313(2) 0.0497(7) Uani 1 1 d . . . . .
O7 O -0.01178(9) 1.4572(2) 0.39931(18) 0.0366(6) Uani 1 1 d . . . . .
O8 O 0.46999(10) 0.4827(2) 0.06409(19) 0.0385(6) Uani 1 1 d . . . . .
N2 N 0.40070(12) 0.7086(3) 0.0758(2) 0.0365(7) Uani 1 1 d . . . . .
N1 N 0.06303(11) 1.2259(3) 0.3961(2) 0.0337(7) Uani 1 1 d . . . . .
C15 C 0.33518(14) 0.4973(3) 0.2383(3) 0.0305(7) Uani 1 1 d . . . . .
C16 C 0.17922(14) 1.2310(3) 0.3503(3) 0.0332(8) Uani 1 1 d . . . . .
C17 C 0.36162(13) 0.5746(3) 0.1874(2) 0.0288(7) Uani 1 1 d . . . . .
N4 N 0.35657(11) 0.7474(3) 0.0783(2) 0.0351(7) Uani 1 1 d . . . . .
C19 C 0.33786(13) 0.6832(3) 0.1320(2) 0.0279(7) Uani 1 1 d . . . . .
C20 C 0.40860(12) 0.5382(3) 0.1872(2) 0.0276(7) Uani 1 1 d . . . . .
C21 C 0.12495(13) 1.4595(3) 0.2387(3) 0.0323(8) Uani 1 1 d . . . . .
C22 C 0.01879(14) 1.5095(3) 0.2271(3) 0.0356(8) Uani 1 1 d . . . . .
C23 C 0.12912(13) 1.4109(3) 0.1500(3) 0.0296(7) Uani 1 1 d . . . . .
C24 C 0.05318(13) 1.4040(3) 0.2895(2) 0.0286(7) Uani 1 1 d . . . . .
N3 N 0.10773(11) 1.1941(3) 0.3921(2) 0.0348(7) Uani 1 1 d . . . . .
C27 C 0.42591(13) 0.6090(3) 0.1291(3) 0.0303(7) Uani 1 1 d . . . . .
C28 C 0.32986(13) 0.5523(3) 0.3242(2) 0.0272(7) Uani 1 1 d . . . . .
C29 C 0.47578(14) 0.5827(3) 0.1201(3) 0.0322(8) Uani 1 1 d . . . . .
C30 C 0.10019(13) 1.3759(3) 0.2892(2) 0.0262(7) Uani 1 1 d . . . . .
C31 C 0.22470(14) 0.9046(4) 0.0975(3) 0.0404(9) Uani 1 1 d . . . . .
H31 H 0.197751 0.845486 0.077002 0.049 Uiso 1 1 calc R . . . .
C32 C 0.35888(13) 0.6568(3) 0.3748(2) 0.0298(7) Uani 1 1 d . . . . .
H32 H 0.381522 0.695157 0.353492 0.036 Uiso 1 1 calc R . . . .
C33 C 0.51485(16) 0.4393(4) 0.0492(3) 0.0428(9) Uani 1 1 d . . . . .
H33A H 0.543989 0.497767 0.079724 0.051 Uiso 1 1 calc R . . . .
H33B H 0.505007 0.434127 -0.022012 0.051 Uiso 1 1 calc R . . . .
C34 C 0.35412(14) 0.7038(3) 0.4565(3) 0.0336(8) Uani 1 1 d . . . . .
H34 H 0.373877 0.773136 0.490928 0.040 Uiso 1 1 calc R . . . .
C35 C 0.31609(14) 0.9544(3) 0.1585(3) 0.0386(8) Uani 1 1 d . . . . .
H35 H 0.350596 0.929338 0.176950 0.046 Uiso 1 1 calc R . . . .
C36 C 0.12584(13) 1.2670(3) 0.3416(2) 0.0288(7) Uani 1 1 d . . . . .
C37 C 0.27615(13) 0.8655(3) 0.1264(2) 0.0315(7) Uani 1 1 d . . . . .
C38 C 0.28566(13) 0.7294(3) 0.1233(2) 0.0300(7) Uani 1 1 d . . . . .
C39 C 0.19212(13) 1.0993(3) 0.3406(2) 0.0322(7) Uani 1 1 d . . . . .
C41 C 0.10141(13) 1.3040(3) 0.0992(3) 0.0332(8) Uani 1 1 d . . . . .
H41 H 0.080973 1.259960 0.122869 0.040 Uiso 1 1 calc R . . . .
C42 C 0.10444(15) 1.2637(3) 0.0136(3) 0.0376(8) Uani 1 1 d . . . . .
H42 H 0.085572 1.193389 -0.020977 0.045 Uiso 1 1 calc R . . . .
C43 C -0.01299(13) 1.3477(3) 0.3572(3) 0.0313(7) Uani 1 1 d . . . . .
C44 C 0.03667(13) 1.3270(3) 0.3463(3) 0.0291(7) Uani 1 1 d . . . . .
C45 C 0.16022(14) 1.4751(3) 0.1144(3) 0.0364(8) Uani 1 1 d . . . . .
H45 H 0.178794 1.546370 0.147685 0.044 Uiso 1 1 calc R . . . .
C46 C 0.30511(17) 1.0796(3) 0.1634(3) 0.0470(10) Uani 1 1 d . . . . .
H46 H 0.332253 1.138316 0.187213 0.056 Uiso 1 1 calc R . . . .
C47 C 0.29579(13) 0.4947(3) 0.3554(3) 0.0326(8) Uani 1 1 d . . . . .
H47 H 0.276733 0.423832 0.322345 0.039 Uiso 1 1 calc R . . . .
C48 C -0.05879(15) 1.4908(4) 0.4102(3) 0.0453(9) Uani 1 1 d . . . . .
H48A H -0.059129 1.447263 0.467027 0.054 Uiso 1 1 calc R . . . .
H48B H -0.090387 1.468306 0.350163 0.054 Uiso 1 1 calc R . . . .
C49 C 0.31983(13) 0.6474(3) 0.4873(3) 0.0342(8) Uani 1 1 d . . . . .
H49 H 0.316518 0.679033 0.542303 0.041 Uiso 1 1 calc R . . . .
C50 C 0.16337(15) 1.4331(4) 0.0302(3) 0.0402(9) Uani 1 1 d . . . . .
H50 H 0.184368 1.475799 0.007173 0.048 Uiso 1 1 calc R . . . .
C51 C 0.29066(14) 0.5445(3) 0.4364(3) 0.0349(8) Uani 1 1 d . . . . .
H51 H 0.267249 0.508049 0.456619 0.042 Uiso 1 1 calc R . . . .
C52 C 0.21306(17) 1.0309(4) 0.0989(3) 0.0519(11) Uani 1 1 d . . . . .
H52 H 0.178386 1.056948 0.077174 0.062 Uiso 1 1 calc R . . . .
C53 C 0.13579(14) 1.3287(4) -0.0203(3) 0.0426(9) Uani 1 1 d . . . . .
H53 H 0.138108 1.301312 -0.077393 0.051 Uiso 1 1 calc R . . . .
C54 C 0.22124(18) 0.8563(4) 0.3219(3) 0.0534(11) Uani 1 1 d . . . . .
H54 H 0.230942 0.774834 0.314926 0.064 Uiso 1 1 calc R . . . .
C55 C 0.44085(15) 0.4302(3) 0.2507(3) 0.0352(8) Uani 1 1 d . . . . .
C56 C 0.25907(17) 0.9475(4) 0.3622(3) 0.0541(11) Uani 1 1 d . . . . .
H56 H 0.294359 0.927149 0.383729 0.065 Uiso 1 1 calc R . . . .
C57 C 0.15402(15) 1.0060(3) 0.3008(3) 0.0375(8) Uani 1 1 d . . . . .
H57 H 0.118709 1.025079 0.280444 0.045 Uiso 1 1 calc R . . . .
C58 C 0.16870(17) 0.8846(4) 0.2916(3) 0.0477(10) Uani 1 1 d . . . . .
H58 H 0.143249 0.822055 0.264946 0.057 Uiso 1 1 calc R . . . .
C60 C 0.25363(17) 1.1175(4) 0.1329(3) 0.0529(11) Uani 1 1 d . . . . .
H60 H 0.246200 1.202095 0.135177 0.064 Uiso 1 1 calc R . . . .
C61 C 0.24517(15) 1.0696(4) 0.3711(3) 0.0424(9) Uani 1 1 d . . . . .
H61 H 0.270884 1.131607 0.397213 0.051 Uiso 1 1 calc R . . . .
C1 C 0.53073(18) 0.3144(4) 0.0959(4) 0.0553(11) Uani 1 1 d . . . . .
H1A H 0.501642 0.257246 0.065442 0.083 Uiso 1 1 calc GR . . . .
H1B H 0.540919 0.320607 0.166487 0.083 Uiso 1 1 calc GR . . . .
H1C H 0.559948 0.284080 0.086253 0.083 Uiso 1 1 calc GR . . . .
C2 C -0.0564(3) 1.6299(5) 0.4264(5) 0.0789(16) Uani 1 1 d . . . . .
H2A H -0.064390 1.672067 0.364313 0.118 Uiso 1 1 calc GR . . . .
H2B H -0.021606 1.652968 0.475614 0.118 Uiso 1 1 calc GR . . . .
H2C H -0.081571 1.653791 0.449709 0.118 Uiso 1 1 calc GR . . . .
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'
F F 0.0171 0.0103 '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'
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
C43 O7 C48 116.2(3) . . ?
C29 O8 C33 118.9(3) . . ?
C27 N2 N4 119.4(3) . . ?
C44 N1 N3 119.0(3) . . ?
O2 C15 C17 117.4(3) . . ?
O2 C15 C28 123.7(3) . . ?
C28 C15 C17 118.9(3) . . ?
O6 C16 C36 115.8(3) . . ?
O6 C16 C39 123.0(3) . . ?
C39 C16 C36 121.1(3) . . ?
C19 C17 C15 121.5(3) . . ?
C20 C17 C15 122.5(3) . . ?
C20 C17 C19 115.8(3) . . ?
C19 N4 N2 119.4(3) . . ?
C17 C19 C38 120.8(3) . . ?
N4 C19 C17 124.0(3) . . ?
N4 C19 C38 115.0(3) . . ?
C17 C20 C27 117.2(3) . . ?
C17 C20 C55 121.5(3) . . ?
C27 C20 C55 121.2(3) . . ?
O4 C21 C23 124.0(3) . . ?
O4 C21 C30 117.3(3) . . ?
C23 C21 C30 118.6(3) . . ?
F4 C22 F5 106.1(3) . . ?
F4 C22 F6 107.6(3) . . ?
F4 C22 C24 111.5(3) . . ?
F5 C22 C24 111.7(3) . . ?
F6 C22 F5 106.6(3) . . ?
F6 C22 C24 112.9(3) . . ?
C41 C23 C21 121.2(3) . . ?
C45 C23 C21 119.3(3) . . ?
C45 C23 C41 119.4(3) . . ?
C30 C24 C22 121.6(3) . . ?
C30 C24 C44 117.7(3) . . ?
C44 C24 C22 120.6(3) . . ?
C36 N3 N1 119.4(3) . . ?
N2 C27 C20 124.0(3) . . ?
N2 C27 C29 111.7(3) . . ?
C20 C27 C29 124.3(3) . . ?
C32 C28 C15 121.4(3) . . ?
C32 C28 C47 120.3(3) . . ?
C47 C28 C15 118.2(3) . . ?
O3 C29 O8 126.1(3) . . ?
O3 C29 C27 123.2(3) . . ?
O8 C29 C27 110.6(3) . . ?
C24 C30 C21 122.7(3) . . ?
C24 C30 C36 116.1(3) . . ?
C36 C30 C21 121.1(3) . . ?
C52 C31 C37 120.7(4) . . ?
C34 C32 C28 120.0(3) . . ?
O8 C33 C1 108.4(3) . . ?
C32 C34 C49 119.9(3) . . ?
C46 C35 C37 120.6(4) . . ?
N3 C36 C16 115.5(3) . . ?
N3 C36 C30 124.0(3) . . ?
C30 C36 C16 120.4(3) . . ?
C31 C37 C38 117.7(3) . . ?
C35 C37 C31 119.1(3) . . ?
C35 C37 C38 123.2(3) . . ?
O1 C38 C19 116.8(3) . . ?
O1 C38 C37 123.0(3) . . ?
C37 C38 C19 120.1(3) . . ?
C57 C39 C16 122.9(3) . . ?
C57 C39 C61 119.6(3) . . ?
C61 C39 C16 117.5(3) . . ?
C42 C41 C23 119.9(3) . . ?
C41 C42 C53 119.8(3) . . ?
O5 C43 O7 126.8(3) . . ?
O5 C43 C44 122.3(3) . . ?
O7 C43 C44 110.9(3) . . ?
N1 C44 C24 123.6(3) . . ?
N1 C44 C43 112.1(3) . . ?
C24 C44 C43 124.3(3) . . ?
C50 C45 C23 120.0(3) . . ?
C35 C46 C60 119.7(4) . . ?
C51 C47 C28 118.9(3) . . ?
O7 C48 C2 106.4(4) . . ?
C51 C49 C34 120.0(3) . . ?
C45 C50 C53 120.6(3) . . ?
C49 C51 C47 120.8(3) . . ?
C60 C52 C31 119.2(4) . . ?
C50 C53 C42 120.3(3) . . ?
C56 C54 C58 120.4(4) . . ?
F1 C55 C20 111.3(3) . . ?
F2 C55 F1 106.7(3) . . ?
F2 C55 F3 107.0(3) . . ?
F2 C55 C20 112.0(3) . . ?
F3 C55 F1 107.1(3) . . ?
F3 C55 C20 112.3(3) . . ?
C54 C56 C61 120.5(4) . . ?
C58 C57 C39 119.9(4) . . ?
C54 C58 C57 120.0(4) . . ?
C46 C60 C52 120.7(4) . . ?
C56 C61 C39 119.6(4) . . ?
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 C55 1.342(4) . ?
F4 C22 1.326(4) . ?
F5 C22 1.345(4) . ?
F2 C55 1.325(4) . ?
F6 C22 1.334(4) . ?
F3 C55 1.333(4) . ?
O4 C21 1.210(4) . ?
O6 C16 1.211(4) . ?
O2 C15 1.211(4) . ?
O1 C38 1.214(4) . ?
O3 C29 1.207(4) . ?
O5 C43 1.199(4) . ?
O7 C43 1.317(4) . ?
O7 C48 1.460(4) . ?
O8 C29 1.317(4) . ?
O8 C33 1.464(4) . ?
N2 N4 1.336(4) . ?
N2 C27 1.326(5) . ?
N1 N3 1.341(4) . ?
N1 C44 1.331(4) . ?
C15 C17 1.527(4) . ?
C15 C28 1.478(5) . ?
C16 C36 1.512(5) . ?
C16 C39 1.473(5) . ?
C17 C19 1.405(5) . ?
C17 C20 1.391(5) . ?
N4 C19 1.332(4) . ?
C19 C38 1.511(5) . ?
C20 C27 1.394(5) . ?
C20 C55 1.510(5) . ?
C21 C23 1.475(5) . ?
C21 C30 1.527(4) . ?
C22 C24 1.505(5) . ?
C23 C41 1.398(5) . ?
C23 C45 1.397(5) . ?
C24 C30 1.370(5) . ?
C24 C44 1.402(5) . ?
N3 C36 1.335(4) . ?
C27 C29 1.508(5) . ?
C28 C32 1.388(5) . ?
C28 C47 1.390(5) . ?
C30 C36 1.406(5) . ?
C31 C37 1.388(5) . ?
C31 C52 1.388(6) . ?
C32 C34 1.380(5) . ?
C33 C1 1.475(6) . ?
C34 C49 1.386(5) . ?
C35 C37 1.387(5) . ?
C35 C46 1.379(5) . ?
C37 C38 1.479(5) . ?
C39 C57 1.391(5) . ?
C39 C61 1.400(5) . ?
C41 C42 1.386(5) . ?
C42 C53 1.391(5) . ?
C43 C44 1.507(5) . ?
C45 C50 1.373(5) . ?
C46 C60 1.381(6) . ?
C47 C51 1.386(5) . ?
C48 C2 1.498(7) . ?
C49 C51 1.377(5) . ?
C50 C53 1.374(5) . ?
C52 C60 1.382(7) . ?
C54 C56 1.371(6) . ?
C54 C58 1.384(6) . ?
C56 C61 1.383(6) . ?
C57 C58 1.385(5) . ?
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
F4 C22 C24 C30 28.7(4) . . . . ?
F4 C22 C24 C44 -148.1(3) . . . . ?
F5 C22 C24 C30 147.2(3) . . . . ?
F5 C22 C24 C44 -29.6(4) . . . . ?
F6 C22 C24 C30 -92.7(4) . . . . ?
F6 C22 C24 C44 90.5(4) . . . . ?
O4 C21 C23 C41 -165.4(4) . . . . ?
O4 C21 C23 C45 12.8(6) . . . . ?
O4 C21 C30 C24 65.9(5) . . . . ?
O4 C21 C30 C36 -111.7(4) . . . . ?
O6 C16 C36 N3 -133.6(3) . . . . ?
O6 C16 C36 C30 42.1(5) . . . . ?
O6 C16 C39 C57 -166.1(4) . . . . ?
O6 C16 C39 C61 12.3(5) . . . . ?
O2 C15 C17 C19 111.8(4) . . . . ?
O2 C15 C17 C20 -64.0(5) . . . . ?
O2 C15 C28 C32 164.2(3) . . . . ?
O2 C15 C28 C47 -14.2(5) . . . . ?
O5 C43 C44 N1 -59.3(5) . . . . ?
O5 C43 C44 C24 120.0(4) . . . . ?
O7 C43 C44 N1 119.7(3) . . . . ?
O7 C43 C44 C24 -61.0(4) . . . . ?
N2 N4 C19 C17 -0.3(5) . . . . ?
N2 N4 C19 C38 -175.6(3) . . . . ?
N2 C27 C29 O3 70.5(4) . . . . ?
N2 C27 C29 O8 -107.2(3) . . . . ?
N1 N3 C36 C16 173.9(3) . . . . ?
N1 N3 C36 C30 -1.6(5) . . . . ?
C15 C17 C19 N4 -173.4(3) . . . . ?
C15 C17 C19 C38 1.7(5) . . . . ?
C15 C17 C20 C27 173.2(3) . . . . ?
C15 C17 C20 C55 -9.5(5) . . . . ?
C15 C28 C32 C34 -178.2(3) . . . . ?
C15 C28 C47 C51 179.5(3) . . . . ?
C16 C39 C57 C58 178.4(4) . . . . ?
C16 C39 C61 C56 -179.2(4) . . . . ?
C17 C15 C28 C32 -15.9(5) . . . . ?
C17 C15 C28 C47 165.7(3) . . . . ?
C17 C19 C38 O1 -38.3(4) . . . . ?
C17 C19 C38 C37 141.1(3) . . . . ?
C17 C20 C27 N2 0.9(5) . . . . ?
C17 C20 C27 C29 -179.9(3) . . . . ?
C17 C20 C55 F1 -30.6(4) . . . . ?
C17 C20 C55 F2 -150.0(3) . . . . ?
C17 C20 C55 F3 89.5(4) . . . . ?
N4 N2 C27 C20 1.6(5) . . . . ?
N4 N2 C27 C29 -177.8(3) . . . . ?
N4 C19 C38 O1 137.1(3) . . . . ?
N4 C19 C38 C37 -43.5(4) . . . . ?
C19 C17 C20 C27 -2.8(4) . . . . ?
C19 C17 C20 C55 174.5(3) . . . . ?
C20 C17 C19 N4 2.7(5) . . . . ?
C20 C17 C19 C38 177.7(3) . . . . ?
C20 C27 C29 O3 -108.8(4) . . . . ?
C20 C27 C29 O8 73.5(4) . . . . ?
C21 C23 C41 C42 177.3(3) . . . . ?
C21 C23 C45 C50 -178.2(3) . . . . ?
C21 C30 C36 C16 0.8(5) . . . . ?
C21 C30 C36 N3 176.0(3) . . . . ?
C22 C24 C30 C21 9.1(5) . . . . ?
C22 C24 C30 C36 -173.2(3) . . . . ?
C22 C24 C44 N1 174.0(3) . . . . ?
C22 C24 C44 C43 -5.2(5) . . . . ?
C23 C21 C30 C24 -113.4(4) . . . . ?
C23 C21 C30 C36 69.0(4) . . . . ?
C23 C41 C42 C53 1.1(5) . . . . ?
C23 C45 C50 C53 0.6(6) . . . . ?
C24 C30 C36 C16 -177.0(3) . . . . ?
C24 C30 C36 N3 -1.7(5) . . . . ?
N3 N1 C44 C24 -0.5(5) . . . . ?
N3 N1 C44 C43 178.9(3) . . . . ?
C27 N2 N4 C19 -1.8(5) . . . . ?
C27 C20 C55 F1 146.6(3) . . . . ?
C27 C20 C55 F2 27.2(4) . . . . ?
C27 C20 C55 F3 -93.3(4) . . . . ?
C28 C15 C17 C19 -68.1(4) . . . . ?
C28 C15 C17 C20 116.2(4) . . . . ?
C28 C32 C34 C49 -0.8(5) . . . . ?
C28 C47 C51 C49 -1.8(5) . . . . ?
C29 O8 C33 C1 115.1(4) . . . . ?
C30 C21 C23 C41 13.8(5) . . . . ?
C30 C21 C23 C45 -168.0(3) . . . . ?
C30 C24 C44 N1 -2.8(5) . . . . ?
C30 C24 C44 C43 177.9(3) . . . . ?
C31 C37 C38 O1 -13.8(5) . . . . ?
C31 C37 C38 C19 166.9(3) . . . . ?
C31 C52 C60 C46 1.2(7) . . . . ?
C32 C28 C47 C51 1.1(5) . . . . ?
C32 C34 C49 C51 0.1(5) . . . . ?
C33 O8 C29 O3 4.5(6) . . . . ?
C33 O8 C29 C27 -177.9(3) . . . . ?
C34 C49 C51 C47 1.2(5) . . . . ?
C35 C37 C38 O1 164.8(4) . . . . ?
C35 C37 C38 C19 -14.5(5) . . . . ?
C35 C46 C60 C52 1.0(7) . . . . ?
C36 C16 C39 C57 15.3(5) . . . . ?
C36 C16 C39 C61 -166.2(3) . . . . ?
C37 C31 C52 C60 -2.3(6) . . . . ?
C37 C35 C46 C60 -2.2(6) . . . . ?
C39 C16 C36 N3 45.1(4) . . . . ?
C39 C16 C36 C30 -139.3(3) . . . . ?
C39 C57 C58 C54 0.0(6) . . . . ?
C41 C23 C45 C50 0.0(5) . . . . ?
C41 C42 C53 C50 -0.5(6) . . . . ?
C43 O7 C48 C2 -161.7(4) . . . . ?
C44 N1 N3 C36 2.6(4) . . . . ?
C44 C24 C30 C21 -174.0(3) . . . . ?
C44 C24 C30 C36 3.7(4) . . . . ?
C45 C23 C41 C42 -0.8(5) . . . . ?
C45 C50 C53 C42 -0.3(6) . . . . ?
C46 C35 C37 C31 1.1(6) . . . . ?
C46 C35 C37 C38 -177.5(4) . . . . ?
C47 C28 C32 C34 0.2(5) . . . . ?
C48 O7 C43 O5 -3.6(5) . . . . ?
C48 O7 C43 C44 177.5(3) . . . . ?
C52 C31 C37 C35 1.2(6) . . . . ?
C52 C31 C37 C38 179.8(4) . . . . ?
C54 C56 C61 C39 1.4(6) . . . . ?
C55 C20 C27 N2 -176.5(3) . . . . ?
C55 C20 C27 C29 2.8(5) . . . . ?
C56 C54 C58 C57 0.7(7) . . . . ?
C57 C39 C61 C56 -0.6(6) . . . . ?
C58 C54 C56 C61 -1.4(7) . . . . ?
C61 C39 C57 C58 0.0(5) . . . . ?
