#------------------------------------------------------------------------------
#$Date: 2017-08-03 04:58:01 +0300 (Thu, 03 Aug 2017) $
#$Revision: 199480 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228839.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_7228839
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), C6 F4 I2'
_chemical_formula_sum            'C16 H10 F4 I2 N6 O2'
_chemical_formula_weight         648.10
_chemical_melting_point          440.15
_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                85.616(2)
_cell_angle_beta                 89.138(2)
_cell_angle_gamma                80.700(2)
_cell_formula_units_Z            1
_cell_length_a                   5.6157(3)
_cell_length_b                   5.8013(3)
_cell_length_c                   15.5403(8)
_cell_measurement_reflns_used    4865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.535
_cell_measurement_theta_min      3.569
_cell_volume                     498.16(5)
_computing_cell_refinement       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8448
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.629
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.220
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0986 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.6923.
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    2.160
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0278
_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)+(0.0156P)²+0.3377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2009
_reflns_number_total             2295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01252g2.cif
_cod_data_source_block           PZA_TFIB
_cod_database_code               7228839
_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   0.739
_shelx_estimated_absorpt_t_min   0.699
_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 1.2896(5) 0.3589(5) 0.0725(2) 0.0667(8) Uani 1 1 d .
N1 N 1.2777(6) 0.7434(7) 0.0329(2) 0.0658(10) Uani 1 1 d .
H1A H 1.4049 0.7181 0.0013 0.079 Uiso 1 1 calc R
H1B H 1.2043 0.8842 0.0370 0.079 Uiso 1 1 calc R
N2 N 0.8705(6) 0.8529(5) 0.1247(2) 0.0529(7) Uani 1 1 d .
N3 N 0.6886(5) 0.5110(5) 0.22987(19) 0.0481(7) Uani 1 1 d .
C1 C 1.1952(6) 0.5665(7) 0.0749(2) 0.0481(8) Uani 1 1 d .
C2 C 0.9737(6) 0.6284(6) 0.1289(2) 0.0403(7) Uani 1 1 d .
C3 C 0.6733(7) 0.9021(7) 0.1727(3) 0.0571(9) Uani 1 1 d .
H3 H 0.5930 1.0557 0.1712 0.069 Uiso 1 1 calc R
C4 C 0.5848(7) 0.7320(7) 0.2245(2) 0.0516(9) Uani 1 1 d .
H4 H 0.4465 0.7747 0.2570 0.062 Uiso 1 1 calc R
C5 C 0.8829(6) 0.4605(6) 0.1809(2) 0.0453(8) Uani 1 1 d .
H5 H 0.9604 0.3060 0.1817 0.054 Uiso 1 1 calc R
I1 I 0.38069(4) 0.27845(4) 0.36228(2) 0.04695(10) Uani 1 1 d .
F1 F 0.2397(4) 0.3204(4) 0.56222(15) 0.0658(6) Uani 1 1 d .
F2 F -0.0420(4) 0.0992(4) 0.66724(13) 0.0609(6) Uani 1 1 d .
C6 C 0.1502(5) 0.1160(5) 0.4448(2) 0.0363(7) Uani 1 1 d .
C7 C 0.1217(6) 0.1627(6) 0.5299(2) 0.0411(7) Uani 1 1 d .
C8 C -0.0248(6) 0.0487(6) 0.5842(2) 0.0391(7) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 115.8(3) . .
C4 N3 C5 115.8(3) . .
O1 C1 N1 124.2(3) . .
O1 C1 C2 119.8(3) . .
N1 C1 C2 116.1(3) . .
N2 C2 C1 117.2(3) . .
N2 C2 C5 121.7(3) . .
C5 C2 C1 121.1(3) . .
N2 C3 H3 119.1 . .
N2 C3 C4 121.8(3) . .
C4 C3 H3 119.1 . .
N3 C4 C3 122.5(3) . .
N3 C4 H4 118.7 . .
C3 C4 H4 118.7 . .
N3 C5 C2 122.3(3) . .
N3 C5 H5 118.8 . .
C2 C5 H5 118.8 . .
C7 C6 I1 122.0(2) . .
C7 C6 C8 117.2(3) . 2_556
C8 C6 I1 120.8(2) 2_556 .
F1 C7 C6 120.2(3) . .
F1 C7 C8 118.5(3) . .
C6 C7 C8 121.3(3) . .
F2 C8 C6 120.0(3) . 2_556
F2 C8 C7 118.5(3) . .
C7 C8 C6 121.5(3) . 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.238(5) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N1 C1 1.318(5) .
N2 C2 1.334(5) .
N2 C3 1.330(5) .
N3 C4 1.317(5) .
N3 C5 1.328(4) .
C1 C2 1.500(5) .
C2 C5 1.374(4) .
C3 H3 0.9300 .
C3 C4 1.377(5) .
C4 H4 0.9300 .
C5 H5 0.9300 .
I1 C6 2.090(3) .
F1 C7 1.344(4) .
F2 C8 1.344(4) .
C6 C7 1.372(5) .
C6 C8 1.380(5) 2_556
C7 C8 1.377(4) .
C8 C6 1.380(5) 2_556
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 2.06 2.916(4) 177.3 2_865
C3 H3 O1 0.93 2.65 3.423(5) 140.4 1_465
C4 H4 F2 0.93 2.57 3.495(4) 174.4 2_566
