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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228841.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_7228841
loop_
_publ_author_name
'Choquesillo-Lazarte, Duane'
'Nemec, Vinko'
'Cinčić, Dominik'
_publ_section_title
;
 Halogen bonded cocrystals of active pharmaceutical ingredients:
 pyrazinamide, lidocaine and pentoxifylline in combination with
 haloperfluorinated compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01252G
_journal_year                    2017
_chemical_formula_moiety         '2(C5 H5 N3 O), Br2 C6 F4'
_chemical_formula_sum            'C16 H10 Br2 F4 N6 O2'
_chemical_formula_weight         554.12
_chemical_melting_point          380.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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   geom
_audit_creation_date             2016-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                98.285(5)
_cell_angle_beta                 90.049(5)
_cell_angle_gamma                102.844(5)
_cell_formula_units_Z            1
_cell_length_a                   5.2164(8)
_cell_length_b                   5.7379(10)
_cell_length_c                   16.463(3)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.236
_cell_measurement_theta_min      2.502
_cell_volume                     475.14(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         2.502
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.331
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0812 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.6769.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0440
_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)+(0.0363P)²+0.6071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1464
_reflns_number_total             2091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01252g2.cif
_cod_data_source_block           PZA_TFBB
_cod_original_cell_volume        475.15(14)
_cod_database_code               7228841
_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   0.671
_shelx_estimated_absorpt_t_min   0.582
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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
O1 O 1.2774(6) 0.6475(5) 0.06337(19) 0.0499(8) Uani 1 1 d .
N1 N 1.2738(7) 0.2494(6) 0.0404(2) 0.0465(9) Uani 1 1 d .
H1A H 1.4030 0.2694 0.0078 0.056 Uiso 1 1 calc R
H1B H 1.2023 0.1069 0.0506 0.056 Uiso 1 1 calc R
N2 N 0.8624(7) 0.1565(6) 0.1398(2) 0.0443(9) Uani 1 1 d .
N3 N 0.6720(7) 0.5327(6) 0.2262(2) 0.0461(9) Uani 1 1 d .
C1 C 1.1850(8) 0.4381(7) 0.0750(2) 0.0374(9) Uani 1 1 d .
C2 C 0.9638(7) 0.3862(6) 0.1319(2) 0.0320(8) Uani 1 1 d .
C3 C 0.6645(9) 0.1181(7) 0.1904(3) 0.0480(11) Uani 1 1 d .
H3 H 0.5860 -0.0399 0.1971 0.058 Uiso 1 1 calc R
C4 C 0.5719(9) 0.3049(7) 0.2332(3) 0.0442(10) Uani 1 1 d .
H4 H 0.4338 0.2691 0.2683 0.053 Uiso 1 1 calc R
C5 C 0.8671(9) 0.5711(7) 0.1744(3) 0.0436(10) Uani 1 1 d .
H5 H 0.9411 0.7290 0.1666 0.052 Uiso 1 1 calc R
Br1 Br 0.34590(10) 0.75822(8) 0.35967(3) 0.0582(2) Uani 1 1 d .
F1 F 0.0164(6) 1.1286(5) 0.34781(17) 0.0644(7) Uani 1 1 d .
F2 F -0.2637(5) 1.3294(5) 0.46220(18) 0.0625(7) Uani 1 1 d .
C6 C 0.1458(8) 0.8947(7) 0.4399(3) 0.0405(10) Uani 1 1 d .
C7 C 0.0111(8) 1.0637(7) 0.4233(2) 0.0418(10) Uani 1 1 d .
C8 C -0.1329(8) 1.1675(7) 0.4824(3) 0.0436(10) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 '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
H1A N1 H1B 120.0 . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
C3 N2 C2 116.1(3) . .
C4 N3 C5 115.8(3) . .
O1 C1 N1 123.7(4) . .
O1 C1 C2 120.2(3) . .
N1 C1 C2 116.1(3) . .
N2 C2 C1 118.1(3) . .
N2 C2 C5 121.3(3) . .
C5 C2 C1 120.7(3) . .
N2 C3 H3 119.0 . .
N2 C3 C4 122.0(4) . .
C4 C3 H3 119.0 . .
N3 C4 C3 122.3(4) . .
N3 C4 H4 118.8 . .
C3 C4 H4 118.8 . .
N3 C5 C2 122.5(4) . .
N3 C5 H5 118.7 . .
C2 C5 H5 118.7 . .
C7 C6 Br1 121.0(3) . .
C7 C6 C8 117.8(4) . 2_576
C8 C6 Br1 121.2(3) 2_576 .
F1 C7 C6 119.9(4) . .
F1 C7 C8 118.8(4) . .
C6 C7 C8 121.3(4) . .
F2 C8 C6 120.5(4) . 2_576
F2 C8 C7 118.6(4) . .
C6 C8 C7 120.9(4) 2_576 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.233(5) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N1 C1 1.326(5) .
N2 C2 1.332(5) .
N2 C3 1.328(5) .
N3 C4 1.317(5) .
N3 C5 1.329(5) .
C1 C2 1.492(5) .
C2 C5 1.376(5) .
C3 H3 0.9300 .
C3 C4 1.375(5) .
C4 H4 0.9300 .
C5 H5 0.9300 .
Br1 C6 1.875(4) .
F1 C7 1.347(5) .
F2 C8 1.345(5) .
C6 C7 1.373(6) .
C6 C8 1.375(6) 2_576
C7 C8 1.378(6) .
C8 C6 1.375(6) 2_576
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
N1 H1A O1 0.86 2.05 2.904(4) 174.1 2_865
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203792
