#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:33:45 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/13/7231372.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_7231372
loop_
_publ_author_name
'Li, Duanxiu'
'Kong, Minmin'
'Li, Jiong'
'Deng, Zongwu'
'Zhang, Hailu'
_publ_section_title
;
 Amine--carboxylate supramolecular synthon in pharmaceutical cocrystals
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              5112
_journal_paper_doi               10.1039/C8CE01106K
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C4 H4 F N3 O, C5 H9 N O2'
_chemical_formula_sum            'C9 H13 F N4 O3'
_chemical_formula_weight         244.23
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-20 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                97.308(4)
_cell_angle_beta                 94.713(4)
_cell_angle_gamma                107.291(5)
_cell_formula_units_Z            2
_cell_length_a                   5.5932(3)
_cell_length_b                   6.0945(4)
_cell_length_c                   16.8563(8)
_cell_measurement_reflns_used    3878
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6680
_cell_measurement_theta_min      5.3240
_cell_volume                     539.79(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5933
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.921
_diffrn_reflns_theta_min         5.334
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 981 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0417
_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)+(0.0909P)²+0.0387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.491
_reflns_Friedel_fraction_full    0.517
_reflns_Friedel_fraction_max     0.476
_reflns_number_gt                3081
_reflns_number_total             3167
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01106k2.cif
_cod_data_source_block           FC-L-Pro
_cod_depositor_comments
'Adding full bibliography for 7231370--7231373.cif.'
_cod_original_cell_volume        539.79(5)
_cod_database_code               7231372
_shelx_shelxl_version_number     2014/7
_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_min   0.659
_shelx_estimated_absorpt_t_max   0.774
loop_
_space_group_symop_operation_xyz
'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
F1 F 0.6569(4) 0.6806(3) 0.06624(12) 0.0460(5) Uani 1 1 d . .
F2 F 0.7646(4) 0.7650(3) 0.53118(11) 0.0444(5) Uani 1 1 d . .
O1 O 1.0985(4) 1.0517(4) 0.36599(13) 0.0366(5) Uani 1 1 d . .
O2 O 0.4086(4) 0.3664(4) 0.22698(12) 0.0351(5) Uani 1 1 d . .
O3 O 0.7640(4) 0.2345(4) 0.98502(14) 0.0395(5) Uani 1 1 d . .
O4 O 0.6020(5) 0.2487(7) 0.86354(16) 0.0681(10) Uani 1 1 d . .
O5 O 0.0483(4) 0.4661(4) 0.64158(15) 0.0417(5) Uani 1 1 d . .
O6 O 0.1943(6) 0.3859(6) 0.75650(17) 0.0628(8) Uani 1 1 d . .
N1 N 0.8266(4) 1.0478(4) 0.25765(15) 0.0320(5) Uani 1 1 d . .
H1A H 0.7903 1.1647 0.2843 0.038 Uiso 1 1 d R U
N2 N 1.0677(4) 0.7915(4) 0.25254(15) 0.0288(5) Uani 1 1 d . .
N3 N 1.0195(5) 0.5218(5) 0.13934(17) 0.0363(6) Uani 1 1 d . .
H3A H 1.131(7) 0.462(6) 0.166(2) 0.032(8) Uiso 1 1 d . .
H3B H 0.942(8) 0.456(7) 0.099(3) 0.037(10) Uiso 1 1 d . .
N4 N 0.4124(4) 0.6307(4) 0.33440(15) 0.0302(5) Uani 1 1 d . .
H4A H 0.2940 0.6610 0.3150 0.036 Uiso 1 1 d R U
N5 N 0.6690(4) 0.3893(4) 0.34095(15) 0.0309(5) Uani 1 1 d . .
N6 N 0.9233(5) 0.4094(5) 0.45787(17) 0.0371(6) Uani 1 1 d . .
H6A H 0.967(7) 0.303(7) 0.429(2) 0.034(9) Uiso 1 1 d . .
H6B H 0.996(8) 0.483(8) 0.510(3) 0.043(10) Uiso 1 1 d . .
N7 N 0.1290(4) 0.1578(4) 0.89511(16) 0.0312(5) Uani 1 1 d . .
H7A H 0.202(7) 0.234(7) 0.856(2) 0.036(9) Uiso 1 1 d . .
H7B H 0.004(8) 0.199(7) 0.914(2) 0.035(9) Uiso 1 1 d . .
N8 N 0.6013(5) 0.3073(4) 0.70415(17) 0.0301(5) Uani 1 1 d . .
H8A H 0.740(10) 0.360(8) 0.696(3) 0.057(13) Uiso 1 1 d . .
H8B H 0.566(8) 0.335(7) 0.750(3) 0.039(10) Uiso 1 1 d . .
C1 C 0.7096(5) 0.9550(5) 0.18208(19) 0.0336(6) Uani 1 1 d . .
H1B H 0.5883 1.0118 0.1588 0.040 Uiso 1 1 calc R U
C2 C 0.7703(5) 0.7817(5) 0.14167(17) 0.0316(6) Uani 1 1 d . .
C3 C 0.9552(5) 0.6951(5) 0.17835(16) 0.0286(6) Uani 1 1 d . .
C4 C 1.0036(5) 0.9668(5) 0.29545(17) 0.0291(6) Uani 1 1 d . .
C5 C 0.4996(5) 0.7361(5) 0.41143(17) 0.0311(6) Uani 1 1 d . .
H5A H 0.4442 0.8562 0.4345 0.037 Uiso 1 1 calc R U
C6 C 0.6675(5) 0.6642(5) 0.45388(17) 0.0310(6) Uani 1 1 d . .
C7 C 0.7552(5) 0.4843(5) 0.41701(16) 0.0278(6) Uani 1 1 d . .
C8 C 0.4922(5) 0.4565(5) 0.29768(17) 0.0285(6) Uani 1 1 d . .
C9 C 0.5853(5) 0.2275(5) 0.93464(18) 0.0318(6) Uani 1 1 d . .
C10 C 0.3260(5) 0.1809(6) 0.96346(18) 0.0354(6) Uani 1 1 d . .
H10A H 0.3279 0.3078 1.0057 0.042 Uiso 1 1 calc R U
C11 C 0.2360(7) -0.0472(9) 0.9931(3) 0.0625(13) Uani 1 1 d . .
H11A H 0.3728 -0.0779 1.0243 0.075 Uiso 1 1 calc R U
H11B H 0.1013 -0.0499 1.0262 0.075 Uiso 1 1 calc R U
C12 C 0.1445(10) -0.2162(8) 0.9191(4) 0.0782(15) Uani 1 1 d . .
H12A H 0.0224 -0.3569 0.9294 0.094 Uiso 1 1 calc R U
H12B H 0.2832 -0.2566 0.8968 0.094 Uiso 1 1 calc R U
C13 C 0.0194(7) -0.0933(7) 0.8602(3) 0.0526(9) Uani 1 1 d . .
H13A H 0.0617 -0.1232 0.8061 0.063 Uiso 1 1 calc R U
H13B H -0.1628 -0.1447 0.8587 0.063 Uiso 1 1 calc R U
C14 C 0.2075(5) 0.4151(5) 0.68560(19) 0.0325(6) Uani 1 1 d . .
C15 C 0.4358(5) 0.3860(5) 0.64681(18) 0.0298(6) Uani 1 1 d . .
H15A H 0.5320 0.5332 0.6312 0.036 Uiso 1 1 calc R U
C16 C 0.3635(6) 0.1924(6) 0.57433(19) 0.0381(6) Uani 1 1 d . .
H16A H 0.4956 0.2120 0.5395 0.046 Uiso 1 1 calc R U
H16B H 0.2072 0.1865 0.5433 0.046 Uiso 1 1 calc R U
C17 C 0.3322(6) -0.0246(5) 0.6136(2) 0.0387(6) Uani 1 1 d . .
H17A H 0.1723 -0.0695 0.6352 0.046 Uiso 1 1 calc R U
H17C H 0.3418 -0.1539 0.5754 0.046 Uiso 1 1 calc R U
C18 C 0.5510(6) 0.0502(5) 0.6802(2) 0.0384(6) Uani 1 1 d . .
H18C H 0.5076 -0.0309 0.7254 0.046 Uiso 1 1 calc R U
H18A H 0.6981 0.0184 0.6610 0.046 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'
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'
F F 0.0727 0.0534 '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
O4 O4 C9 0(10) 1
O6 O6 C14 0(10) 1
C1 N1 C4 122.7(2) .
C1 N1 H1A 119.7 .
C4 N1 H1A 117.6 .
C3 N2 C4 121.3(2) .
C3 N3 H3A 119(2) .
C3 N3 H3B 119(3) .
H3A N3 H3B 121(4) .
C5 N4 C8 122.5(2) .
C5 N4 H4A 114.7 .
C8 N4 H4A 121.9 .
C7 N5 C8 121.3(3) .
C7 N6 H6A 113(3) .
C7 N6 H6B 120(3) .
H6A N6 H6B 126(4) .
C13 N7 C10 108.3(3) .
C13 N7 H7A 108(2) .
C10 N7 H7A 109(2) .
C13 N7 H7B 106(3) .
C10 N7 H7B 109(3) .
H7A N7 H7B 116(4) .
C15 N8 C18 108.4(2) .
C15 N8 H8A 107(4) .
C18 N8 H8A 103(4) .
C15 N8 H8B 109(3) .
C18 N8 H8B 110(3) .
H8A N8 H8B 119(5) .
C2 C1 N1 119.1(2) .
C2 C1 H1B 120.5 .
N1 C1 H1B 120.5 .
C1 C2 F1 121.5(2) .
C1 C2 C3 119.9(3) .
F1 C2 C3 118.6(3) .
N3 C3 N2 119.4(2) .
N3 C3 C2 121.2(3) .
N2 C3 C2 119.4(3) .
O1 C4 N2 122.2(2) .
O1 C4 N1 120.3(3) .
N2 C4 N1 117.5(2) .
C6 C5 N4 118.8(3) .
C6 C5 H5A 120.6 .
N4 C5 H5A 120.6 .
C5 C6 F2 121.6(3) .
C5 C6 C7 119.9(3) .
F2 C6 C7 118.5(2) .
N5 C7 N6 119.5(3) .
N5 C7 C6 119.4(2) .
N6 C7 C6 121.2(3) .
O2 C8 N4 120.3(2) .
O2 C8 N5 121.6(3) .
N4 C8 N5 118.1(3) .
O4 C9 O4 0.00(3) 1
O4 C9 O3 124.8(3) 1
O4 C9 O3 124.8(3) .
O4 C9 C10 118.3(2) 1
O4 C9 C10 118.3(2) .
O3 C9 C10 116.8(3) .
N7 C10 C11 103.0(3) .
N7 C10 C9 110.6(2) .
C11 C10 C9 113.5(3) .
N7 C10 H10A 109.9 .
C11 C10 H10A 109.9 .
C9 C10 H10A 109.9 .
C12 C11 C10 103.6(3) .
C12 C11 H11A 111.0 .
C10 C11 H11A 111.0 .
C12 C11 H11B 111.0 .
C10 C11 H11B 111.0 .
H11A C11 H11B 109.0 .
C11 C12 C13 105.3(4) .
C11 C12 H12A 110.7 .
C13 C12 H12A 110.7 .
C11 C12 H12B 110.7 .
C13 C12 H12B 110.7 .
H12A C12 H12B 108.8 .
N7 C13 C12 103.4(3) .
N7 C13 H13A 111.1 .
C12 C13 H13A 111.1 .
N7 C13 H13B 111.1 .
C12 C13 H13B 111.1 .
H13A C13 H13B 109.1 .
O6 C14 O6 0.0(6) 1
O6 C14 O5 125.6(3) 1
O6 C14 O5 125.6(3) .
O6 C14 C15 118.4(3) 1
O6 C14 C15 118.4(3) .
O5 C14 C15 115.9(3) .
N8 C15 C16 103.3(2) .
N8 C15 C14 110.3(2) .
C16 C15 C14 112.8(2) .
N8 C15 H15A 110.1 .
C16 C15 H15A 110.1 .
C14 C15 H15A 110.1 .
C15 C16 C17 102.4(2) .
C15 C16 H16A 111.3 .
C17 C16 H16A 111.3 .
C15 C16 H16B 111.3 .
C17 C16 H16B 111.3 .
H16A C16 H16B 109.2 .
C18 C17 C16 103.3(2) .
C18 C17 H17A 111.1 .
C16 C17 H17A 111.1 .
C18 C17 H17C 111.1 .
C16 C17 H17C 111.1 .
H17A C17 H17C 109.1 .
N8 C18 C17 105.1(2) .
N8 C18 H18C 110.7 .
C17 C18 H18C 110.7 .
N8 C18 H18A 110.7 .
C17 C18 H18A 110.7 .
H18C C18 H18A 108.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.354(3) .
F2 C6 1.361(3) .
O1 C4 1.241(4) .
O2 C8 1.237(3) .
O3 C9 1.244(4) .
O4 O4 0.000(5) 1
O4 C9 1.230(4) .
O5 C14 1.247(4) .
O6 O6 0.000(11) 1
O6 C14 1.235(4) .
N1 C1 1.353(4) .
N1 C4 1.377(3) .
N1 H1A 0.8773 .
N2 C3 1.330(4) .
N2 C4 1.366(4) .
N3 C3 1.329(4) .
N3 H3A 0.93(4) .
N3 H3B 0.77(5) .
N4 C5 1.354(4) .
N4 C8 1.367(4) .
N4 H4A 0.7949 .
N5 C7 1.325(4) .
N5 C8 1.370(3) .
N6 C7 1.340(4) .
N6 H6A 0.86(4) .
N6 H6B 0.94(5) .
N7 C13 1.489(4) .
N7 C10 1.490(3) .
N7 H7A 0.91(4) .
N7 H7B 0.88(4) .
N8 C15 1.502(3) .
N8 C18 1.502(4) .
N8 H8A 0.78(6) .
N8 H8B 0.82(5) .
C1 C2 1.327(4) .
C1 H1B 0.9300 .
C2 C3 1.426(4) .
C5 C6 1.341(4) .
C5 H5A 0.9300 .
C6 C7 1.423(4) .
C9 O4 1.230(4) 1
C9 C10 1.525(4) .
C10 C11 1.496(5) .
C10 H10A 0.9800 .
C11 C12 1.462(8) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.557(7) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 O6 1.235(4) 1
C14 C15 1.527(4) .
C15 C16 1.522(4) .
C15 H15A 0.9800 .
C16 C17 1.524(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.509(4) .
C17 H17A 0.9700 .
C17 H17C 0.9700 .
C18 H18C 0.9700 .
C18 H18A 0.9700 .
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
N3 H3B F1 0.77(5) 2.46(4) 2.762(3) 105(4) .
N6 H6B F2 0.94(5) 2.45(4) 2.767(4) 100(3) .
N7 H7A O4 0.91(4) 2.21(4) 2.650(3) 109(3) .
N8 H8B O6 0.82(5) 2.20(4) 2.657(4) 115(4) .
N1 H1A N5 0.88 1.89 2.762(3) 172.5 1_565
N3 H3A O2 0.93(4) 2.05(4) 2.978(3) 173(3) 1_655
N3 H3B O3 0.77(5) 2.18(5) 2.936(4) 171(4) 1_554
N4 H4A N2 0.79 1.98 2.759(3) 164.8 1_455
N6 H6A O1 0.86(4) 2.10(5) 2.962(4) 176(4) 1_545
N6 H6B O5 0.94(5) 2.23(5) 3.070(4) 149(4) 1_655
N7 H7A O6 0.91(4) 2.02(4) 2.862(4) 154(3) 1
N7 H7B O4 0.88(4) 2.45(4) 3.173(4) 139(3) 1_455
N8 H8A O5 0.78(6) 1.99(6) 2.749(3) 164(5) 1_655
N8 H8B O4 0.82(5) 2.06(4) 2.755(4) 142(4) 1
