#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:20:42 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246251.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_7246251
loop_
_publ_author_name
'Alfuth, Jan'
'Kazimierczuk, Katarzyna'
'Połoński, Tadeusz'
'Olszewska, Teresa'
_publ_section_title
;
 Self-assembly of secondary aryl amides in cocrystals with perfluoroaryl
 coformers: structural analysis and synthon preferences
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1403
_journal_page_last               1410
_journal_paper_doi               10.1039/D2CE01710E
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H7 N O, C6 H F5 O '
_chemical_formula_sum            'C17 H8 F5 N O2'
_chemical_formula_weight         353.24
_chemical_name_systematic
;
benzo[cd]indol-2(1H)-one -- perfluorophenol  
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2023-02-03
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-02-03 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                98.454(8)
_cell_angle_beta                 97.155(8)
_cell_angle_gamma                100.557(8)
_cell_formula_units_Z            4
_cell_length_a                   9.0463(9)
_cell_length_b                   11.6765(12)
_cell_length_c                   13.7306(14)
_cell_measurement_reflns_used    13839
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.40
_cell_measurement_theta_min      2.66
_cell_volume                     1393.1(3)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22130
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_min         2.318
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         7482
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0727P)²+2.1247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.177
_refine_ls_wR_factor_ref         0.1837
_reflns_Friedel_coverage         0
_reflns_number_gt                6231
_reflns_number_total             7482
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01710e2.cif
_cod_data_source_block           to9_2022
_cod_depositor_comments
'Adding full bibliography for 7246246--7246251.cif.'
_cod_database_code               7246251
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6706(3) 0.94382(19) 0.58266(17) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.7721(2) 0.91442(18) 0.66520(16) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.8909(3) 0.8554(2) 0.67140(19) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.92645 0.822611 0.61348 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9577(3) 0.8461(2) 0.7686(2) 0.0286(5) Uani 1 1 d . . . . .
H4 H 1.039942 0.806083 0.774747 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9087(3) 0.8923(2) 0.85444(19) 0.0282(5) Uani 1 1 d . . . . .
H5 H 0.957226 0.883211 0.917495 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7865(2) 0.95317(19) 0.84928(16) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.7236(2) 0.96028(18) 0.75281(15) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.6000(2) 1.01413(18) 0.73094(16) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.5339(3) 1.0651(2) 0.80588(17) 0.0256(4) Uani 1 1 d . . . . .
H9 H 0.449897 1.101793 0.792519 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5982(3) 1.0601(2) 0.90549(18) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.555332 1.095546 0.959007 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7181(3) 1.0069(2) 0.92790(17) 0.0278(5) Uani 1 1 d . . . . .
H11 H 0.755803 1.005769 0.995409 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9556(4) 0.4814(4) 0.3476(2) 0.0251(6) Uani 0.907(6) 1 d D . P A 1
C13 C 0.8901(2) 0.48342(19) 0.24360(17) 0.0235(4) Uani 1 1 d D . . . .
C14 C 0.9231(3) 0.4409(2) 0.15109(19) 0.0285(5) Uani 1 1 d . . . . .
H14 H 1.003048 0.399075 0.144603 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8328(3) 0.4622(2) 0.06658(18) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.853328 0.433256 0.002341 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7162(3) 0.5230(2) 0.07321(18) 0.0283(5) Uani 1 1 d . . . . .
H16 H 0.659589 0.535677 0.014092 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6802(2) 0.56681(19) 0.16707(16) 0.0224(4) Uani 1 1 d . . . . .
C18 C 0.7704(2) 0.54432(17) 0.24934(16) 0.0201(4) Uani 1 1 d . . . . .
C19 C 0.7540(3) 0.57907(19) 0.34864(17) 0.0242(4) Uani 1 1 d D . . . .
C20 C 0.6439(3) 0.6389(2) 0.37110(19) 0.0291(5) Uani 1 1 d . . . . .
H20 H 0.630573 0.663006 0.438042 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5492(3) 0.6639(2) 0.2889(2) 0.0309(5) Uani 1 1 d . . . . .
H21 H 0.471443 0.705755 0.302668 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5644(3) 0.6305(2) 0.19047(19) 0.0279(5) Uani 1 1 d . . . . .
H22 H 0.498416 0.64964 0.138629 0.033 Uiso 1 1 calc R U . . .
C23 C 0.9011(2) 0.86476(19) 0.29364(17) 0.0243(4) Uani 1 1 d . . . . .
C24 C 1.0085(3) 0.8266(2) 0.35584(17) 0.0262(4) Uani 1 1 d . . . . .
C25 C 1.1108(3) 0.7640(2) 0.31886(18) 0.0264(4) Uani 1 1 d . . . . .
C26 C 1.1082(2) 0.73800(19) 0.21728(18) 0.0250(4) Uani 1 1 d . . . . .
C27 C 1.0038(3) 0.77536(19) 0.15402(16) 0.0244(4) Uani 1 1 d . . . . .
C28 C 0.9014(2) 0.83764(19) 0.19169(17) 0.0237(4) Uani 1 1 d . . . . .
C29 C 0.5731(3) 0.6424(2) 0.6756(2) 0.0222(5) Uani 0.897(4) 1 d D . P B 1
C30 C 0.4522(3) 0.6900(2) 0.6379(2) 0.0230(5) Uani 0.897(4) 1 d D . P B 1
C31 C 0.3693(4) 0.7466(3) 0.69984(19) 0.0222(6) Uani 0.897(4) 1 d D . P B 1
C32 C 0.4051(5) 0.7582(6) 0.8023(2) 0.0218(10) Uani 0.897(4) 1 d D . P B 1
C33 C 0.5230(5) 0.7104(5) 0.8410(3) 0.0246(7) Uani 0.897(4) 1 d D U P B 1
C34 C 0.6057(3) 0.6534(2) 0.7785(3) 0.0232(5) Uani 0.897(4) 1 d D . P B 1
F1 F 1.01358(19) 0.85173(15) 0.45527(11) 0.0370(4) Uani 1 1 d . . . . .
F2 F 1.21223(18) 0.72805(15) 0.38077(12) 0.0376(4) Uani 1 1 d . . . . .
F3 F 1.20610(17) 0.67596(13) 0.18056(13) 0.0359(4) Uani 1 1 d . . . . .
F4 F 1.00022(18) 0.74971(14) 0.05505(11) 0.0339(3) Uani 1 1 d . . . . .
F5 F 0.80028(17) 0.87136(14) 0.12805(11) 0.0336(3) Uani 1 1 d . . . . .
F6 F 0.41619(19) 0.68165(16) 0.53914(12) 0.0325(4) Uani 0.897(4) 1 d D . P B 1
F7 F 0.2543(2) 0.79201(19) 0.66102(14) 0.0313(4) Uani 0.897(4) 1 d D . P B 1
F8 F 0.3228(5) 0.8120(4) 0.8628(3) 0.0293(7) Uani 0.897(4) 1 d D . P B 1
F9 F 0.5589(3) 0.7194(2) 0.94050(17) 0.0322(5) Uani 0.897(4) 1 d D . P B 1
F10 F 0.72009(17) 0.60715(14) 0.81779(14) 0.0297(4) Uani 0.897(4) 1 d D . P B 1
N1 N 0.5699(2) 1.00206(17) 0.62648(14) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.496677 1.028149 0.593639 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8687(4) 0.5379(4) 0.4065(3) 0.0246(7) Uani 0.907(6) 1 d D . P A 1
H2 H 0.882539 0.547489 0.471976 0.03 Uiso 0.907(6) 1 calc R U P A 1
O2 O 1.0630(2) 0.43823(16) 0.37866(14) 0.0265(5) Uani 0.907(6) 1 d D . P A 1
O1 O 0.6709(2) 0.92250(16) 0.49146(12) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.8017(2) 0.92797(16) 0.32677(14) 0.0306(4) Uani 1 1 d . . . . .
H3A H 0.793246 0.919905 0.385743 0.046 Uiso 1 1 calc R U . . .
O4 O 0.6497(2) 0.58852(18) 0.61061(14) 0.0280(5) Uani 0.897(4) 1 d D . P B 1
H4A H 0.740268 0.595204 0.637447 0.042 Uiso 0.897(4) 1 calc R U P B 1
C31A C 0.399(4) 0.730(4) 0.7006(16) 0.038(13) Uiso 0.103(4) 1 d D . P B 2
F7A F 0.289(2) 0.7672(18) 0.6475(15) 0.038(5) Uiso 0.103(4) 1 d D . P B 2
C32A C 0.398(4) 0.738(4) 0.8028(15) 0.025(13) Uiso 0.103(4) 1 d D . P B 2
F8A F 0.315(5) 0.811(4) 0.845(2) 0.028(8) Uiso 0.103(4) 1 d D . P B 2
C33A C 0.521(4) 0.714(4) 0.8611(15) 0.012(4) Uiso 0.103(4) 1 d D U P B 2
F9A F 0.534(3) 0.734(2) 0.9607(14) 0.031(6) Uiso 0.103(4) 1 d D . P B 2
C34A C 0.619(3) 0.653(3) 0.8167(14) 0.032(7) Uiso 0.103(4) 1 d D . P B 2
F10A F 0.7274(16) 0.6199(13) 0.8755(13) 0.032(4) Uiso 0.103(4) 1 d D . P B 2
C29A C 0.613(2) 0.6337(18) 0.7149(14) 0.022(5) Uiso 0.103(4) 1 d D . P B 2
O4A O 0.7077(19) 0.5718(14) 0.6709(13) 0.030(4) Uiso 0.103(4) 1 d D . P B 2
H4AA H 0.656026 0.510795 0.632976 0.045 Uiso 0.103(4) 1 calc R U P B 2
C30A C 0.500(2) 0.6704(15) 0.6582(11) 0.011(4) Uiso 0.103(4) 1 d D . P B 2
F6A F 0.4825(19) 0.6488(13) 0.5583(10) 0.032(4) Uiso 0.103(4) 1 d D . P B 2
N2A N 0.927(4) 0.492(3) 0.3543(14) 0.02 Uiso 0.093(6) 1 d D U P A 2
H2A H 0.996185 0.453052 0.375538 0.024 Uiso 0.093(6) 1 calc R U P A 2
C12A C 0.864(5) 0.552(6) 0.4256(14) 0.037(16) Uiso 0.093(6) 1 d D . P A 2
O2A O 0.8375(19) 0.5758(15) 0.5122(12) 0.025(5) Uiso 0.093(6) 1 d D . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
O1 C1 N1 124.2(2) . . ?
O1 C1 C2 129.2(2) . . ?
N1 C1 C2 106.51(18) . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 135.3(2) . . ?
C7 C2 C1 105.48(18) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 123.2(2) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 114.6(2) . . ?
C7 C6 C11 115.7(2) . . ?
C5 C6 C11 129.7(2) . . ?
C6 C7 C2 125.6(2) . . ?
C6 C7 C8 123.8(2) . . ?
C2 C7 C8 110.60(19) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 N1 132.7(2) . . ?
C7 C8 N1 106.68(18) . . ?
C8 C9 C10 116.4(2) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 123.6(2) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C10 C11 C6 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
O2 C12 N2 125.2(3) . . ?
O2 C12 C13 129.4(3) . . ?
N2 C12 C13 105.5(2) . . ?
C14 C13 C18 119.3(2) . . ?
C14 C13 C12 134.3(2) . . ?
C18 C13 C12 106.5(2) . . ?
C14 C13 N2A 146.4(11) . . ?
C18 C13 N2A 94.3(11) . . ?
C13 C14 C15 117.3(2) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C16 C15 C14 122.9(2) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 115.3(2) . . ?
C18 C17 C22 115.0(2) . . ?
C16 C17 C22 129.7(2) . . ?
C17 C18 C19 124.8(2) . . ?
C17 C18 C13 124.5(2) . . ?
C19 C18 C13 110.70(19) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 N2 134.1(3) . . ?
C18 C19 N2 105.5(3) . . ?
C20 C19 C12A 122.5(10) . . ?
C18 C19 C12A 117.1(9) . . ?
C19 C20 C21 116.5(2) . . ?
C19 C20 H20 121.7 . . ?
C21 C20 H20 121.7 . . ?
C22 C21 C20 123.7(2) . . ?
C22 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C21 C22 C17 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
O3 C23 C28 119.1(2) . . ?
O3 C23 C24 123.8(2) . . ?
C28 C23 C24 117.0(2) . . ?
F1 C24 C25 118.8(2) . . ?
F1 C24 C23 119.2(2) . . ?
C25 C24 C23 122.0(2) . . ?
F2 C25 C26 119.8(2) . . ?
F2 C25 C24 120.5(2) . . ?
C26 C25 C24 119.7(2) . . ?
F3 C26 C27 120.4(2) . . ?
F3 C26 C25 120.1(2) . . ?
C27 C26 C25 119.5(2) . . ?
F4 C27 C26 119.7(2) . . ?
F4 C27 C28 119.9(2) . . ?
C26 C27 C28 120.4(2) . . ?
F5 C28 C27 118.9(2) . . ?
F5 C28 C23 119.8(2) . . ?
C27 C28 C23 121.3(2) . . ?
O4 C29 C34 124.5(2) . . ?
O4 C29 C30 118.4(2) . . ?
C34 C29 C30 117.1(2) . . ?
F6 C30 C31 119.0(3) . . ?
F6 C30 C29 119.4(2) . . ?
C31 C30 C29 121.6(3) . . ?
F7 C31 C30 120.0(2) . . ?
F7 C31 C32 119.6(3) . . ?
C30 C31 C32 120.4(3) . . ?
F8 C32 C33 120.7(3) . . ?
F8 C32 C31 120.4(4) . . ?
C33 C32 C31 118.9(3) . . ?
F9 C33 C32 120.0(3) . . ?
F9 C33 C34 119.6(3) . . ?
C32 C33 C34 120.5(3) . . ?
F10 C34 C33 119.5(3) . . ?
F10 C34 C29 118.9(2) . . ?
C33 C34 C29 121.6(2) . . ?
C1 N1 C8 110.72(18) . . ?
C1 N1 H1 124.6 . . ?
C8 N1 H1 124.6 . . ?
C12 N2 C19 111.9(3) . . ?
C12 N2 H2 124.1 . . ?
C19 N2 H2 124.1 . . ?
C23 O3 H3A 109.5 . . ?
C29 O4 H4A 109.5 . . ?
F7A C31A C30A 123.3(18) . . ?
F7A C31A C32A 117.6(17) . . ?
C30A C31A C32A 118.5(17) . . ?
F8A C32A C33A 119(2) . . ?
F8A C32A C31A 117(2) . . ?
C33A C32A C31A 119(2) . . ?
F9A C33A C34A 119.3(16) . . ?
F9A C33A C32A 120.5(17) . . ?
C34A C33A C32A 119.6(17) . . ?
F10A C34A C29A 120.4(16) . . ?
F10A C34A C33A 118.3(16) . . ?
C29A C34A C33A 121.1(15) . . ?
O4A C29A C34A 121.2(16) . . ?
O4A C29A C30A 120.7(15) . . ?
C34A C29A C30A 117.9(14) . . ?
C29A O4A H4AA 109.5 . . ?
F6A C30A C31A 116.8(16) . . ?
F6A C30A C29A 121.2(14) . . ?
C31A C30A C29A 122.0(14) . . ?
C12A N2A C13 127(2) . . ?
C12A N2A H2A 116.6 . . ?
C13 N2A H2A 116.6 . . ?
O2A C12A N2A 152(3) . . ?
O2A C12A C19 115(2) . . ?
N2A C12A C19 90.8(18) . . ?
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
C1 O1 1.241(3) . ?
C1 N1 1.378(3) . ?
C1 C2 1.488(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.423(3) . ?
C3 H3 0.95 . ?
C4 C5 1.381(4) . ?
C4 H4 0.95 . ?
C5 C6 1.420(3) . ?
C5 H5 0.95 . ?
C6 C7 1.395(3) . ?
C6 C11 1.432(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.369(3) . ?
C8 N1 1.407(3) . ?
C9 C10 1.432(3) . ?
C9 H9 0.95 . ?
C10 C11 1.369(3) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 O2 1.234(3) . ?
C12 N2 1.378(5) . ?
C12 C13 1.481(4) . ?
C13 C14 1.383(3) . ?
C13 C18 1.405(3) . ?
C13 N2A 1.500(19) . ?
C14 C15 1.413(4) . ?
C14 H14 0.95 . ?
C15 C16 1.381(4) . ?
C15 H15 0.95 . ?
C16 C17 1.414(3) . ?
C16 H16 0.95 . ?
C17 C18 1.395(3) . ?
C17 C22 1.433(3) . ?
C18 C19 1.398(3) . ?
C19 C20 1.358(3) . ?
C19 N2 1.424(3) . ?
C19 C12A 1.47(2) . ?
C20 C21 1.428(4) . ?
C20 H20 0.95 . ?
C21 C22 1.381(4) . ?
C21 H21 0.95 . ?
C22 H22 0.95 . ?
C23 O3 1.344(3) . ?
C23 C28 1.390(3) . ?
C23 C24 1.391(3) . ?
C24 F1 1.347(3) . ?
C24 C25 1.380(3) . ?
C25 F2 1.339(3) . ?
C25 C26 1.379(3) . ?
C26 F3 1.343(2) . ?
C26 C27 1.377(3) . ?
C27 F4 1.343(3) . ?
C27 C28 1.382(3) . ?
C28 F5 1.338(2) . ?
C29 O4 1.350(3) . ?
C29 C34 1.388(4) . ?
C29 C30 1.393(3) . ?
C30 F6 1.339(3) . ?
C30 C31 1.378(4) . ?
C31 F7 1.340(4) . ?
C31 C32 1.384(4) . ?
C32 F8 1.346(3) . ?
C32 C33 1.376(4) . ?
C33 F9 1.348(4) . ?
C33 C34 1.383(4) . ?
C34 F10 1.344(3) . ?
N1 H1 0.88 . ?
N2 H2 0.88 . ?
O3 H3A 0.84 . ?
O4 H4A 0.84 . ?
C31A F7A 1.335(17) . ?
C31A C30A 1.377(17) . ?
C31A C32A 1.394(17) . ?
C32A F8A 1.352(18) . ?
C32A C33A 1.382(17) . ?
C33A F9A 1.340(16) . ?
C33A C34A 1.377(16) . ?
C34A F10A 1.341(16) . ?
C34A C29A 1.375(17) . ?
C29A O4A 1.360(16) . ?
C29A C30A 1.377(16) . ?
O4A H4AA 0.84 . ?
C30A F6A 1.341(15) . ?
N2A C12A 1.366(18) . ?
N2A H2A 0.88 . ?
C12A O2A 1.244(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 2.02 2.896(2) 175.2 2_676 yes
N2^a H2^a O2^a 0.88 2.02 2.899(4) 173.2 2_766 yes
O3 H3A O1 0.84 1.93 2.683(2) 148.3 . yes
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
O1 C1 C2 C3 -1.9(4) . . . . ?
N1 C1 C2 C3 178.1(2) . . . . ?
O1 C1 C2 C7 179.1(2) . . . . ?
N1 C1 C2 C7 -0.9(2) . . . . ?
C7 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C11 179.8(2) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C11 C6 C7 C2 179.9(2) . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
C1 C2 C7 C6 179.9(2) . . . . ?
C3 C2 C7 C8 -178.55(19) . . . . ?
C1 C2 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C2 C7 C8 C9 179.9(2) . . . . ?
C6 C7 C8 N1 -179.37(19) . . . . ?
C2 C7 C8 N1 -0.1(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
N1 C8 C9 C10 -179.8(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 0.4(3) . . . . ?
C5 C6 C11 C10 -179.0(2) . . . . ?
O2 C12 C13 C14 0.1(6) . . . . ?
N2 C12 C13 C14 -179.0(3) . . . . ?
O2 C12 C13 C18 -179.5(4) . . . . ?
N2 C12 C13 C18 1.4(4) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
N2A C13 C14 C15 177(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C22 -179.4(2) . . . . ?
C16 C17 C18 C19 -179.7(2) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C22 C17 C18 C13 180.0(2) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
N2A C13 C18 C17 -178.8(15) . . . . ?
C14 C13 C18 C19 179.4(2) . . . . ?
C12 C13 C18 C19 -0.9(3) . . . . ?
N2A C13 C18 C19 1.1(15) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C13 C18 C19 C20 -179.7(2) . . . . ?
C17 C18 C19 N2 -180.0(3) . . . . ?
C13 C18 C19 N2 0.1(3) . . . . ?
C17 C18 C19 C12A -177(3) . . . . ?
C13 C18 C19 C12A 3(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
N2 C19 C20 C21 180.0(3) . . . . ?
C12A C19 C20 C21 177(3) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C16 C17 C22 C21 179.4(2) . . . . ?
O3 C23 C24 F1 1.2(3) . . . . ?
C28 C23 C24 F1 179.4(2) . . . . ?
O3 C23 C24 C25 -178.6(2) . . . . ?
C28 C23 C24 C25 -0.4(3) . . . . ?
F1 C24 C25 F2 0.6(3) . . . . ?
C23 C24 C25 F2 -179.6(2) . . . . ?
F1 C24 C25 C26 -179.6(2) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
F2 C25 C26 F3 0.5(3) . . . . ?
C24 C25 C26 F3 -179.2(2) . . . . ?
F2 C25 C26 C27 -179.9(2) . . . . ?
C24 C25 C26 C27 0.3(3) . . . . ?
F3 C26 C27 F4 -0.1(3) . . . . ?
C25 C26 C27 F4 -179.7(2) . . . . ?
F3 C26 C27 C28 179.0(2) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
F4 C27 C28 F5 -0.1(3) . . . . ?
C26 C27 C28 F5 -179.2(2) . . . . ?
F4 C27 C28 C23 179.4(2) . . . . ?
C26 C27 C28 C23 0.3(3) . . . . ?
O3 C23 C28 F5 -2.1(3) . . . . ?
C24 C23 C28 F5 179.6(2) . . . . ?
O3 C23 C28 C27 178.4(2) . . . . ?
C24 C23 C28 C27 0.1(3) . . . . ?
O4 C29 C30 F6 -0.3(4) . . . . ?
C34 C29 C30 F6 -180.0(2) . . . . ?
O4 C29 C30 C31 -179.8(3) . . . . ?
C34 C29 C30 C31 0.6(4) . . . . ?
F6 C30 C31 F7 0.1(4) . . . . ?
C29 C30 C31 F7 179.6(3) . . . . ?
F6 C30 C31 C32 -179.1(4) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
F7 C31 C32 F8 1.7(8) . . . . ?
C30 C31 C32 F8 -179.1(5) . . . . ?
F7 C31 C32 C33 179.6(4) . . . . ?
C30 C31 C32 C33 -1.2(7) . . . . ?
F8 C32 C33 F9 -1.4(9) . . . . ?
C31 C32 C33 F9 -179.3(5) . . . . ?
F8 C32 C33 C34 178.9(5) . . . . ?
C31 C32 C33 C34 1.0(8) . . . . ?
F9 C33 C34 F10 0.4(6) . . . . ?
C32 C33 C34 F10 -179.9(4) . . . . ?
F9 C33 C34 C29 -179.8(3) . . . . ?
C32 C33 C34 C29 -0.1(7) . . . . ?
O4 C29 C34 F10 -0.5(4) . . . . ?
C30 C29 C34 F10 179.1(2) . . . . ?
O4 C29 C34 C33 179.7(3) . . . . ?
C30 C29 C34 C33 -0.7(4) . . . . ?
O1 C1 N1 C8 -179.1(2) . . . . ?
C2 C1 N1 C8 0.9(2) . . . . ?
C9 C8 N1 C1 179.4(2) . . . . ?
C7 C8 N1 C1 -0.5(2) . . . . ?
O2 C12 N2 C19 179.5(4) . . . . ?
C13 C12 N2 C19 -1.4(4) . . . . ?
C20 C19 N2 C12 -179.4(3) . . . . ?
C18 C19 N2 C12 0.9(4) . . . . ?
F7A C31A C32A F8A -18(7) . . . . ?
C30A C31A C32A F8A 171(4) . . . . ?
F7A C31A C32A C33A -172(4) . . . . ?
C30A C31A C32A C33A 16(7) . . . . ?
F8A C32A C33A F9A 18(7) . . . . ?
C31A C32A C33A F9A 172(4) . . . . ?
F8A C32A C33A C34A -171(5) . . . . ?
C31A C32A C33A C34A -17(7) . . . . ?
F9A C33A C34A F10A -2(6) . . . . ?
C32A C33A C34A F10A -173(4) . . . . ?
F9A C33A C34A C29A -178(3) . . . . ?
C32A C33A C34A C29A 11(6) . . . . ?
F10A C34A C29A O4A 6(4) . . . . ?
C33A C34A C29A O4A -179(3) . . . . ?
F10A C34A C29A C30A -180(2) . . . . ?
C33A C34A C29A C30A -4(5) . . . . ?
F7A C31A C30A F6A -1(5) . . . . ?
C32A C31A C30A F6A 170(4) . . . . ?
F7A C31A C30A C29A 180(3) . . . . ?
C32A C31A C30A C29A -9(6) . . . . ?
O4A C29A C30A F6A -2(3) . . . . ?
C34A C29A C30A F6A -177(2) . . . . ?
O4A C29A C30A C31A 178(3) . . . . ?
C34A C29A C30A C31A 3(4) . . . . ?
C14 C13 N2A C12A 177(4) . . . . ?
C18 C13 N2A C12A -6(5) . . . . ?
C13 N2A C12A O2A 165(10) . . . . ?
C13 N2A C12A C19 7(6) . . . . ?
C20 C19 C12A O2A 9(7) . . . . ?
C18 C19 C12A O2A -174(4) . . . . ?
C20 C19 C12A N2A 177(2) . . . . ?
C18 C19 C12A N2A -5(5) . . . . ?
