#------------------------------------------------------------------------------
#$Date: 2022-10-28 00:55:04 +0300 (Fri, 28 Oct 2022) $
#$Revision: 278835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/09/7130927.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_7130927
loop_
_publ_author_name
'Pu, Liang-Yuan'
'Zhang, Yu-Jiao'
'Liu, Wei'
'Teng, Fan'
_publ_section_title
;
 Chiral phosphoric acid-catalyzed dual ring formation for enantioselective
 construction of N--N axially chiral 3,3’-bisquinazolinones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05172A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H16 F2 N4 O2'
_chemical_formula_sum            'C28 H16 F2 N4 O2'
_chemical_formula_weight         478.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-31 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9059(2)
_cell_length_b                   13.4075(4)
_cell_length_c                   37.5682(10)
_cell_measurement_reflns_used    9696
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      68.288
_cell_measurement_theta_min      2.352
_cell_volume                     4485.9(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            305524
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.386
_diffrn_reflns_theta_min         2.352
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.7944.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         8242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0293
_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)+(0.0384P)²+0.5971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                8121
_reflns_number_total             8242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc05172a2.cif
_cod_data_source_block           cu_20220709g_0m_a
_cod_database_code               7130927
_shelx_shelxl_version_number     2019/2
_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   0.854
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F1A)=Sof(H10)=1-FVAR(1)
 Sof(F1)=Sof(H14)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27),
  C28(H28), C31(H31), C32(H32), C33(H33), C34(H34), C39(H39), C40(H40),
 C41(H41), C42(H42), C45(H45), C46(H46), C47(H47), C48(H48), C53(H53), C54(H54),
  C55(H55), C56(H56)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
F1 F 0.3882(2) 0.25765(14) 0.62243(5) 0.0775(7) Uani 0.776(4) 1 d . . P A 1
F1A F 0.1175(9) 0.4601(5) 0.54745(19) 0.080(3) Uani 0.224(4) 1 d . . P A 2
F2 F 0.5714(2) 0.30172(12) 0.54332(5) 0.0865(5) Uani 1 1 d . . . . .
O1 O 0.49813(19) 0.66962(11) 0.61776(4) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.1977(2) 0.64954(15) 0.57071(5) 0.0775(5) Uani 1 1 d . . . . .
N1 N 0.2161(2) 0.44097(13) 0.64343(4) 0.0474(4) Uani 1 1 d . . . . .
N2 N 0.37546(19) 0.52609(12) 0.60374(4) 0.0441(4) Uani 1 1 d . . . . .
N3 N 0.40092(19) 0.54692(12) 0.56790(4) 0.0451(4) Uani 1 1 d . . . . .
N4 N 0.5437(2) 0.52099(16) 0.51642(5) 0.0589(5) Uani 1 1 d . . . . .
C1 C 0.4157(2) 0.60300(15) 0.62757(5) 0.0442(4) Uani 1 1 d . . . . .
C2 C 0.3472(2) 0.59252(15) 0.66252(5) 0.0431(4) Uani 1 1 d . . . . .
C3 C 0.3750(3) 0.66304(16) 0.68901(5) 0.0519(5) Uani 1 1 d . . . . .
H3 H 0.445448 0.713179 0.685351 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2971(3) 0.65781(17) 0.72063(5) 0.0598(6) Uani 1 1 d . . . . .
H4 H 0.315610 0.704389 0.738439 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1918(3) 0.58377(18) 0.72603(5) 0.0626(6) Uani 1 1 d . . . . .
H5 H 0.138223 0.582033 0.747272 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1648(3) 0.51278(17) 0.70054(5) 0.0542(5) Uani 1 1 d . . . . .
H6 H 0.094471 0.462832 0.704619 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2436(2) 0.51586(15) 0.66842(5) 0.0446(4) Uani 1 1 d . . . . .
C8 C 0.2774(2) 0.44782(15) 0.61277(5) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.2515(2) 0.36631(16) 0.58669(5) 0.0484(5) Uani 1 1 d . . . . .
C10 C 0.3018(3) 0.27123(17) 0.59457(6) 0.0594(5) Uani 1 1 d . . . . .
H10 H 0.360597 0.261722 0.614742 0.071 Uiso 0.224(4) 1 calc R U P A 2
C11 C 0.2675(3) 0.18997(19) 0.57351(8) 0.0756(7) Uani 1 1 d . . . . .
H11 H 0.301496 0.126628 0.579585 0.091 Uiso 1 1 calc R U . . .
C12 C 0.1827(4) 0.2042(2) 0.54354(7) 0.0781(8) Uani 1 1 d . . . . .
H12 H 0.160055 0.150200 0.528949 0.094 Uiso 1 1 calc R U . . .
C13 C 0.1308(4) 0.2978(2) 0.53484(6) 0.0749(8) Uani 1 1 d . . . . .
H13 H 0.072956 0.306928 0.514489 0.090 Uiso 1 1 calc R U . . .
C14 C 0.1646(3) 0.37766(19) 0.55629(6) 0.0603(6) Uani 1 1 d . . . . .
H14 H 0.128661 0.440592 0.550312 0.072 Uiso 0.776(4) 1 calc R U P A 1
C15 C 0.2978(3) 0.61452(16) 0.55272(6) 0.0533(5) Uani 1 1 d . . . . .
C16 C 0.3245(3) 0.63149(16) 0.51500(6) 0.0567(5) Uani 1 1 d . . . . .
C17 C 0.2303(4) 0.69481(19) 0.49566(7) 0.0760(8) Uani 1 1 d . . . . .
H17 H 0.152759 0.728773 0.506976 0.091 Uiso 1 1 calc R U . . .
C18 C 0.2535(5) 0.7063(2) 0.45971(8) 0.0920(11) Uani 1 1 d . . . . .
H18 H 0.193650 0.749961 0.446725 0.110 Uiso 1 1 calc R U . . .
C19 C 0.3664(4) 0.6529(3) 0.44279(7) 0.0901(10) Uani 1 1 d . . . . .
H19 H 0.378650 0.659188 0.418309 0.108 Uiso 1 1 calc R U . . .
C20 C 0.4590(4) 0.5915(3) 0.46133(6) 0.0790(8) Uani 1 1 d . . . . .
H20 H 0.534563 0.556876 0.449546 0.095 Uiso 1 1 calc R U . . .
C21 C 0.4412(3) 0.58034(18) 0.49809(6) 0.0576(6) Uani 1 1 d . . . . .
C22 C 0.5242(2) 0.50755(15) 0.54987(5) 0.0469(4) Uani 1 1 d . . . . .
C23 C 0.6376(2) 0.45197(16) 0.57084(5) 0.0494(5) Uani 1 1 d . . . . .
C24 C 0.6608(3) 0.35097(17) 0.56643(6) 0.0588(5) Uani 1 1 d . . . . .
C25 C 0.7718(3) 0.3000(2) 0.58474(8) 0.0738(7) Uani 1 1 d . . . . .
H25 H 0.783921 0.231643 0.581609 0.089 Uiso 1 1 calc R U . . .
C26 C 0.8634(3) 0.3513(2) 0.60748(7) 0.0710(7) Uani 1 1 d . . . . .
H26 H 0.938382 0.317831 0.619876 0.085 Uiso 1 1 calc R U . . .
C27 C 0.8452(3) 0.4516(2) 0.61205(7) 0.0671(6) Uani 1 1 d . . . . .
H27 H 0.908895 0.486313 0.627273 0.080 Uiso 1 1 calc R U . . .
C28 C 0.7329(3) 0.50180(19) 0.59424(6) 0.0602(5) Uani 1 1 d . . . . .
H28 H 0.720586 0.569914 0.597909 0.072 Uiso 1 1 calc R U . . .
F3 F 0.52274(17) 0.48751(13) 0.37666(4) 0.0815(4) Uani 1 1 d . . . . .
F4 F 0.47892(16) 0.56626(13) 0.27830(4) 0.0805(4) Uani 1 1 d . . . . .
O3 O -0.08690(17) 0.61659(12) 0.34561(4) 0.0614(4) Uani 1 1 d . . . . .
O4 O -0.05625(19) 0.40115(13) 0.30719(5) 0.0669(4) Uani 1 1 d . . . . .
N5 N 0.2132(2) 0.44111(13) 0.39770(4) 0.0479(4) Uani 1 1 d . . . . .
N6 N 0.11906(17) 0.51644(12) 0.34608(4) 0.0442(4) Uani 1 1 d . . . . .
N7 N 0.11677(18) 0.52629(13) 0.30896(4) 0.0449(4) Uani 1 1 d . . . . .
N8 N 0.1496(2) 0.64283(14) 0.26260(5) 0.0516(4) Uani 1 1 d . . . . .
C29 C -0.0009(2) 0.56674(15) 0.36317(6) 0.0474(4) Uani 1 1 d . . . . .
C30 C -0.0057(2) 0.55086(15) 0.40130(6) 0.0479(4) Uani 1 1 d . . . . .
C31 C -0.1179(3) 0.59643(18) 0.42200(7) 0.0609(6) Uani 1 1 d . . . . .
H31 H -0.187009 0.639441 0.411560 0.073 Uiso 1 1 calc R U . . .
C32 C -0.1242(3) 0.5767(2) 0.45773(7) 0.0696(7) Uani 1 1 d . . . . .
H32 H -0.198492 0.606079 0.471593 0.083 Uiso 1 1 calc R U . . .
C33 C -0.0209(3) 0.5134(2) 0.47336(6) 0.0677(6) Uani 1 1 d . . . . .
H33 H -0.027186 0.500452 0.497632 0.081 Uiso 1 1 calc R U . . .
C34 C 0.0907(3) 0.46941(18) 0.45369(6) 0.0590(5) Uani 1 1 d . . . . .
H34 H 0.160007 0.427552 0.464628 0.071 Uiso 1 1 calc R U . . .
C35 C 0.0998(2) 0.48780(15) 0.41709(6) 0.0477(4) Uani 1 1 d . . . . .
C36 C 0.2193(2) 0.45431(14) 0.36402(5) 0.0432(4) Uani 1 1 d . . . . .
C37 C 0.3386(2) 0.40201(16) 0.34352(5) 0.0470(4) Uani 1 1 d . . . . .
C38 C 0.4875(3) 0.41868(19) 0.35178(6) 0.0587(5) Uani 1 1 d . . . . .
C39 C 0.6028(3) 0.3681(2) 0.33528(8) 0.0752(8) Uani 1 1 d . . . . .
H39 H 0.702320 0.381567 0.341024 0.090 Uiso 1 1 calc R U . . .
C40 C 0.5676(3) 0.2969(2) 0.31007(8) 0.0770(8) Uani 1 1 d . . . . .
H40 H 0.644104 0.262552 0.298519 0.092 Uiso 1 1 calc R U . . .
C41 C 0.4210(3) 0.2766(2) 0.30192(7) 0.0680(7) Uani 1 1 d . . . . .
H41 H 0.398385 0.227272 0.285350 0.082 Uiso 1 1 calc R U . . .
C42 C 0.3059(3) 0.32911(17) 0.31827(6) 0.0550(5) Uani 1 1 d . . . . .
H42 H 0.206597 0.315614 0.312348 0.066 Uiso 1 1 calc R U . . .
C43 C -0.0008(2) 0.47249(17) 0.29222(6) 0.0513(5) Uani 1 1 d . . . . .
C44 C -0.0416(2) 0.51226(18) 0.25747(6) 0.0544(5) Uani 1 1 d . . . . .
C45 C -0.1580(3) 0.4676(2) 0.23789(7) 0.0723(7) Uani 1 1 d . . . . .
H45 H -0.208315 0.412252 0.246822 0.087 Uiso 1 1 calc R U . . .
C46 C -0.1964(3) 0.5069(3) 0.20534(8) 0.0834(9) Uani 1 1 d . . . . .
H46 H -0.273052 0.477759 0.192136 0.100 Uiso 1 1 calc R U . . .
C47 C -0.1214(4) 0.5897(3) 0.19203(7) 0.0792(8) Uani 1 1 d . . . . .
H47 H -0.148047 0.615078 0.169868 0.095 Uiso 1 1 calc R U . . .
C48 C -0.0090(3) 0.6346(2) 0.21101(6) 0.0671(6) Uani 1 1 d . . . . .
H48 H 0.039594 0.690433 0.201922 0.080 Uiso 1 1 calc R U . . .
C49 C 0.0322(2) 0.59593(17) 0.24419(5) 0.0521(5) Uani 1 1 d . . . . .
C50 C 0.1839(2) 0.61035(15) 0.29353(5) 0.0437(4) Uani 1 1 d . . . . .
C51 C 0.3101(2) 0.65683(15) 0.31358(5) 0.0438(4) Uani 1 1 d . . . . .
C52 C 0.4561(2) 0.63188(17) 0.30509(6) 0.0521(5) Uani 1 1 d . . . . .
C53 C 0.5779(3) 0.6690(2) 0.32273(7) 0.0647(6) Uani 1 1 d . . . . .
H53 H 0.674601 0.649326 0.316602 0.078 Uiso 1 1 calc R U . . .
C54 C 0.5539(3) 0.7362(2) 0.34982(7) 0.0654(6) Uani 1 1 d . . . . .
H54 H 0.635040 0.761664 0.362447 0.078 Uiso 1 1 calc R U . . .
C55 C 0.4108(3) 0.76571(18) 0.35829(6) 0.0627(6) Uani 1 1 d . . . . .
H55 H 0.395815 0.812939 0.376064 0.075 Uiso 1 1 calc R U . . .
C56 C 0.2888(3) 0.72579(17) 0.34059(6) 0.0562(5) Uani 1 1 d . . . . .
H56 H 0.192118 0.745263 0.346830 0.067 Uiso 1 1 calc R U . . .
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
C8 N1 C7 118.64(18) . . ?
N3 N2 C1 115.15(15) . . ?
N3 N2 C8 118.91(15) . . ?
C8 N2 C1 123.33(15) . . ?
N2 N3 C15 114.42(16) . . ?
N2 N3 C22 121.45(16) . . ?
C22 N3 C15 124.03(17) . . ?
C22 N4 C21 118.5(2) . . ?
O1 C1 N2 119.89(17) . . ?
O1 C1 C2 126.80(19) . . ?
N2 C1 C2 113.30(17) . . ?
C3 C2 C1 120.29(19) . . ?
C3 C2 C7 120.13(18) . . ?
C7 C2 C1 119.37(17) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
N1 C7 C2 122.53(17) . . ?
N1 C7 C6 118.13(19) . . ?
C6 C7 C2 119.34(19) . . ?
N1 C8 N2 122.42(18) . . ?
N1 C8 C9 118.38(18) . . ?
N2 C8 C9 119.07(16) . . ?
C10 C9 C8 119.09(19) . . ?
C10 C9 C14 117.2(2) . . ?
C14 C9 C8 123.3(2) . . ?
F1 C10 C9 119.3(2) . . ?
F1 C10 C11 118.5(2) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
F1A C14 C9 120.8(4) . . ?
F1A C14 C13 117.9(4) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.3 . . ?
O2 C15 N3 120.12(19) . . ?
O2 C15 C16 127.0(2) . . ?
N3 C15 C16 112.8(2) . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 C21 120.5(2) . . ?
C21 C16 C15 119.2(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
N4 C21 C16 122.86(19) . . ?
N4 C21 C20 118.4(2) . . ?
C16 C21 C20 118.7(2) . . ?
N3 C22 C23 117.97(16) . . ?
N4 C22 N3 122.0(2) . . ?
N4 C22 C23 119.98(19) . . ?
C24 C23 C22 122.1(2) . . ?
C24 C23 C28 117.1(2) . . ?
C28 C23 C22 120.64(19) . . ?
F2 C24 C23 117.9(2) . . ?
F2 C24 C25 119.9(2) . . ?
C23 C24 C25 122.1(2) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 C24 119.2(2) . . ?
C26 C25 H25 120.4 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C36 N5 C35 119.05(17) . . ?
N7 N6 C29 113.27(15) . . ?
C36 N6 N7 123.14(16) . . ?
C36 N6 C29 123.22(16) . . ?
N6 N7 C43 113.84(16) . . ?
N6 N7 C50 118.78(16) . . ?
C50 N7 C43 122.71(16) . . ?
C50 N8 C49 118.27(19) . . ?
O3 C29 N6 119.49(19) . . ?
O3 C29 C30 126.9(2) . . ?
N6 C29 C30 113.60(17) . . ?
C31 C30 C29 120.3(2) . . ?
C35 C30 C29 119.27(19) . . ?
C35 C30 C31 120.4(2) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.2(2) . . ?
C32 C31 H31 120.4 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.5(2) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.1(2) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(2) . . ?
C35 C34 H34 120.1 . . ?
N5 C35 C30 122.52(18) . . ?
N5 C35 C34 118.5(2) . . ?
C30 C35 C34 119.0(2) . . ?
N5 C36 N6 122.27(18) . . ?
N5 C36 C37 118.49(17) . . ?
N6 C36 C37 119.24(16) . . ?
C38 C37 C36 119.6(2) . . ?
C38 C37 C42 117.9(2) . . ?
C42 C37 C36 122.30(19) . . ?
F3 C38 C37 119.3(2) . . ?
F3 C38 C39 118.3(2) . . ?
C39 C38 C37 122.4(3) . . ?
C38 C39 H39 120.7 . . ?
C38 C39 C40 118.7(3) . . ?
C40 C39 H39 120.7 . . ?
C39 C40 H40 119.7 . . ?
C41 C40 C39 120.5(2) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.3(3) . . ?
C42 C41 H41 119.8 . . ?
C37 C42 H42 119.9 . . ?
C41 C42 C37 120.3(2) . . ?
C41 C42 H42 119.9 . . ?
O4 C43 N7 119.69(19) . . ?
O4 C43 C44 127.0(2) . . ?
N7 C43 C44 113.29(19) . . ?
C45 C44 C43 119.8(2) . . ?
C49 C44 C43 119.89(19) . . ?
C49 C44 C45 120.3(2) . . ?
C44 C45 H45 120.5 . . ?
C46 C45 C44 119.1(3) . . ?
C46 C45 H45 120.5 . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.5(3) . . ?
C47 C46 H46 119.8 . . ?
C46 C47 H47 119.5 . . ?
C48 C47 C46 121.0(3) . . ?
C48 C47 H47 119.5 . . ?
C47 C48 H48 120.2 . . ?
C47 C48 C49 119.6(3) . . ?
C49 C48 H48 120.2 . . ?
C44 C49 N8 122.43(18) . . ?
C44 C49 C48 119.6(2) . . ?
C48 C49 N8 118.0(2) . . ?
N7 C50 C51 116.69(16) . . ?
N8 C50 N7 123.26(18) . . ?
N8 C50 C51 119.82(18) . . ?
C52 C51 C50 119.54(18) . . ?
C52 C51 C56 117.4(2) . . ?
C56 C51 C50 123.09(19) . . ?
F4 C52 C51 118.12(19) . . ?
F4 C52 C53 118.6(2) . . ?
C53 C52 C51 123.2(2) . . ?
C52 C53 H53 120.8 . . ?
C52 C53 C54 118.3(2) . . ?
C54 C53 H53 120.8 . . ?
C53 C54 H54 119.8 . . ?
C55 C54 C53 120.3(2) . . ?
C55 C54 H54 119.8 . . ?
C54 C55 H55 119.8 . . ?
C54 C55 C56 120.5(2) . . ?
C56 C55 H55 119.8 . . ?
C51 C56 H56 119.9 . . ?
C55 C56 C51 120.2(2) . . ?
C55 C56 H56 119.9 . . ?
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 C10 1.312(3) . ?
F1A C14 1.228(7) . ?
F2 C24 1.351(3) . ?
O1 C1 1.214(3) . ?
O2 C15 1.213(3) . ?
N1 C7 1.396(3) . ?
N1 C8 1.278(3) . ?
N2 N3 1.394(2) . ?
N2 C1 1.412(3) . ?
N2 C8 1.407(3) . ?
N3 C15 1.411(3) . ?
N3 C22 1.394(3) . ?
N4 C21 1.393(3) . ?
N4 C22 1.281(3) . ?
C1 C2 1.454(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.399(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(3) . ?
C8 C9 1.486(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.455(3) . ?
C16 C17 1.397(4) . ?
C16 C21 1.398(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.357(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(3) . ?
C22 C23 1.482(3) . ?
C23 C24 1.380(3) . ?
C23 C28 1.393(3) . ?
C24 C25 1.385(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.367(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.365(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(3) . ?
C28 H28 0.9300 . ?
F3 C38 1.351(3) . ?
F4 C52 1.352(3) . ?
O3 C29 1.212(2) . ?
O4 C43 1.215(3) . ?
N5 C35 1.394(3) . ?
N5 C36 1.279(2) . ?
N6 N7 1.401(2) . ?
N6 C29 1.417(3) . ?
N6 C36 1.394(2) . ?
N7 C43 1.418(3) . ?
N7 C50 1.401(3) . ?
N8 C49 1.402(3) . ?
N8 C50 1.278(2) . ?
C29 C30 1.449(3) . ?
C30 C31 1.406(3) . ?
C30 C35 1.397(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.369(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.382(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.399(3) . ?
C36 C37 1.488(3) . ?
C37 C38 1.380(3) . ?
C37 C42 1.393(3) . ?
C38 C39 1.378(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.380(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.369(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.387(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.456(3) . ?
C44 C45 1.405(3) . ?
C44 C49 1.393(3) . ?
C45 H45 0.9300 . ?
C45 C46 1.374(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.389(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.368(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.399(3) . ?
C50 C51 1.490(3) . ?
C51 C52 1.380(3) . ?
C51 C56 1.386(3) . ?
C52 C53 1.365(3) . ?
C53 H53 0.9300 . ?
C53 C54 1.376(4) . ?
C54 H54 0.9300 . ?
C54 C55 1.372(4) . ?
C55 H55 0.9300 . ?
C55 C56 1.381(3) . ?
C56 H56 0.9300 . ?
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 C10 C11 C12 -177.2(3) . . . . ?
F2 C24 C25 C26 178.7(2) . . . . ?
O1 C1 C2 C3 -0.6(3) . . . . ?
O1 C1 C2 C7 174.1(2) . . . . ?
O2 C15 C16 C17 0.7(4) . . . . ?
O2 C15 C16 C21 -176.5(2) . . . . ?
N1 C8 C9 C10 -62.7(3) . . . . ?
N1 C8 C9 C14 110.0(2) . . . . ?
N2 N3 C15 O2 0.2(3) . . . . ?
N2 N3 C15 C16 -177.83(17) . . . . ?
N2 N3 C22 N4 175.52(19) . . . . ?
N2 N3 C22 C23 -6.8(3) . . . . ?
N2 C1 C2 C3 -179.51(18) . . . . ?
N2 C1 C2 C7 -4.8(3) . . . . ?
N2 C8 C9 C10 113.3(2) . . . . ?
N2 C8 C9 C14 -74.0(3) . . . . ?
N3 N2 C1 O1 -16.8(3) . . . . ?
N3 N2 C1 C2 162.21(16) . . . . ?
N3 N2 C8 N1 -160.26(18) . . . . ?
N3 N2 C8 C9 23.9(3) . . . . ?
N3 C15 C16 C17 178.6(2) . . . . ?
N3 C15 C16 C21 1.4(3) . . . . ?
N3 C22 C23 C24 113.5(2) . . . . ?
N3 C22 C23 C28 -71.0(3) . . . . ?
N4 C22 C23 C24 -68.8(3) . . . . ?
N4 C22 C23 C28 106.7(2) . . . . ?
C1 N2 N3 C15 -74.3(2) . . . . ?
C1 N2 N3 C22 102.2(2) . . . . ?
C1 N2 C8 N1 0.5(3) . . . . ?
C1 N2 C8 C9 -175.33(18) . . . . ?
C1 C2 C3 C4 173.2(2) . . . . ?
C1 C2 C7 N1 8.0(3) . . . . ?
C1 C2 C7 C6 -172.51(19) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C2 C7 N1 -177.29(18) . . . . ?
C3 C2 C7 C6 2.2(3) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 N1 178.4(2) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
C7 N1 C8 N2 2.3(3) . . . . ?
C7 N1 C8 C9 178.12(18) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C8 N1 C7 C2 -6.6(3) . . . . ?
C8 N1 C7 C6 173.9(2) . . . . ?
C8 N2 N3 C15 88.0(2) . . . . ?
C8 N2 N3 C22 -95.5(2) . . . . ?
C8 N2 C1 O1 -178.24(18) . . . . ?
C8 N2 C1 C2 0.8(3) . . . . ?
C8 C9 C10 F1 -9.1(3) . . . . ?
C8 C9 C10 C11 172.8(2) . . . . ?
C8 C9 C14 F1A 7.9(6) . . . . ?
C8 C9 C14 C13 -173.1(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C9 C14 F1A -179.3(5) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 F1A 179.3(5) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C14 C9 C10 F1 177.8(2) . . . . ?
C14 C9 C10 C11 -0.3(4) . . . . ?
C15 N3 C22 N4 -8.4(3) . . . . ?
C15 N3 C22 C23 169.31(19) . . . . ?
C15 C16 C17 C18 -177.1(2) . . . . ?
C15 C16 C21 N4 -6.7(3) . . . . ?
C15 C16 C21 C20 175.3(2) . . . . ?
C16 C17 C18 C19 2.1(4) . . . . ?
C17 C16 C21 N4 176.1(2) . . . . ?
C17 C16 C21 C20 -1.8(3) . . . . ?
C17 C18 C19 C20 -2.5(5) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 N4 -176.5(3) . . . . ?
C19 C20 C21 C16 1.5(4) . . . . ?
C21 N4 C22 N3 2.7(3) . . . . ?
C21 N4 C22 C23 -174.9(2) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
C22 N3 C15 O2 -176.1(2) . . . . ?
C22 N3 C15 C16 5.8(3) . . . . ?
C22 N4 C21 C16 4.7(3) . . . . ?
C22 N4 C21 C20 -177.4(2) . . . . ?
C22 C23 C24 F2 -3.1(3) . . . . ?
C22 C23 C24 C25 176.7(2) . . . . ?
C22 C23 C28 C27 -175.7(2) . . . . ?
C23 C24 C25 C26 -1.2(4) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 1.0(4) . . . . ?
C26 C27 C28 C23 -1.1(4) . . . . ?
C28 C23 C24 F2 -178.8(2) . . . . ?
C28 C23 C24 C25 1.1(3) . . . . ?
F3 C38 C39 C40 179.4(2) . . . . ?
F4 C52 C53 C54 179.6(2) . . . . ?
O3 C29 C30 C31 -0.7(3) . . . . ?
O3 C29 C30 C35 177.7(2) . . . . ?
O4 C43 C44 C45 0.9(4) . . . . ?
O4 C43 C44 C49 179.2(2) . . . . ?
N5 C36 C37 C38 -58.9(3) . . . . ?
N5 C36 C37 C42 114.9(2) . . . . ?
N6 N7 C43 O4 -23.4(3) . . . . ?
N6 N7 C43 C44 156.55(17) . . . . ?
N6 N7 C50 N8 -157.43(18) . . . . ?
N6 N7 C50 C51 28.1(2) . . . . ?
N6 C29 C30 C31 179.60(18) . . . . ?
N6 C29 C30 C35 -2.0(3) . . . . ?
N6 C36 C37 C38 120.6(2) . . . . ?
N6 C36 C37 C42 -65.6(3) . . . . ?
N7 N6 C29 O3 -4.0(3) . . . . ?
N7 N6 C29 C30 175.69(16) . . . . ?
N7 N6 C36 N5 -175.20(18) . . . . ?
N7 N6 C36 C37 5.4(3) . . . . ?
N7 C43 C44 C45 -179.1(2) . . . . ?
N7 C43 C44 C49 -0.7(3) . . . . ?
N7 C50 C51 C52 96.0(2) . . . . ?
N7 C50 C51 C56 -84.7(2) . . . . ?
N8 C50 C51 C52 -78.7(3) . . . . ?
N8 C50 C51 C56 100.7(2) . . . . ?
C29 N6 N7 C43 -71.0(2) . . . . ?
C29 N6 N7 C50 85.4(2) . . . . ?
C29 N6 C36 N5 -2.6(3) . . . . ?
C29 N6 C36 C37 177.93(18) . . . . ?
C29 C30 C31 C32 177.1(2) . . . . ?
C29 C30 C35 N5 1.8(3) . . . . ?
C29 C30 C35 C34 -177.3(2) . . . . ?
C30 C31 C32 C33 0.5(4) . . . . ?
C31 C30 C35 N5 -179.9(2) . . . . ?
C31 C30 C35 C34 1.0(3) . . . . ?
C31 C32 C33 C34 0.4(4) . . . . ?
C32 C33 C34 C35 -0.7(4) . . . . ?
C33 C34 C35 N5 -179.2(2) . . . . ?
C33 C34 C35 C30 -0.1(3) . . . . ?
C35 N5 C36 N6 2.1(3) . . . . ?
C35 N5 C36 C37 -178.49(17) . . . . ?
C35 C30 C31 C32 -1.3(3) . . . . ?
C36 N5 C35 C30 -1.7(3) . . . . ?
C36 N5 C35 C34 177.4(2) . . . . ?
C36 N6 N7 C43 102.2(2) . . . . ?
C36 N6 N7 C50 -101.3(2) . . . . ?
C36 N6 C29 O3 -177.25(19) . . . . ?
C36 N6 C29 C30 2.5(3) . . . . ?
C36 C37 C38 F3 -4.6(3) . . . . ?
C36 C37 C38 C39 176.0(2) . . . . ?
C36 C37 C42 C41 -174.7(2) . . . . ?
C37 C38 C39 C40 -1.2(4) . . . . ?
C38 C37 C42 C41 -0.8(3) . . . . ?
C38 C39 C40 C41 -0.6(4) . . . . ?
C39 C40 C41 C42 1.7(4) . . . . ?
C40 C41 C42 C37 -1.0(4) . . . . ?
C42 C37 C38 F3 -178.72(19) . . . . ?
C42 C37 C38 C39 1.9(3) . . . . ?
C43 N7 C50 N8 -3.2(3) . . . . ?
C43 N7 C50 C51 -177.67(18) . . . . ?
C43 C44 C45 C46 179.2(2) . . . . ?
C43 C44 C49 N8 2.1(3) . . . . ?
C43 C44 C49 C48 -179.1(2) . . . . ?
C44 C45 C46 C47 -0.2(4) . . . . ?
C45 C44 C49 N8 -179.6(2) . . . . ?
C45 C44 C49 C48 -0.7(3) . . . . ?
C45 C46 C47 C48 -0.6(5) . . . . ?
C46 C47 C48 C49 0.7(4) . . . . ?
C47 C48 C49 N8 178.9(2) . . . . ?
C47 C48 C49 C44 0.0(4) . . . . ?
C49 N8 C50 N7 4.3(3) . . . . ?
C49 N8 C50 C51 178.66(18) . . . . ?
C49 C44 C45 C46 0.8(4) . . . . ?
C50 N7 C43 O4 -178.77(19) . . . . ?
C50 N7 C43 C44 1.1(3) . . . . ?
C50 N8 C49 C44 -3.9(3) . . . . ?
C50 N8 C49 C48 177.3(2) . . . . ?
C50 C51 C52 F4 0.7(3) . . . . ?
C50 C51 C52 C53 -178.2(2) . . . . ?
C50 C51 C56 C55 179.6(2) . . . . ?
C51 C52 C53 C54 -1.4(4) . . . . ?
C52 C51 C56 C55 -1.0(3) . . . . ?
C52 C53 C54 C55 -1.0(4) . . . . ?
C53 C54 C55 C56 2.3(4) . . . . ?
C54 C55 C56 C51 -1.3(4) . . . . ?
C56 C51 C52 F4 -178.66(19) . . . . ?
C56 C51 C52 C53 2.4(3) . . . . ?
