#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/77/4507756.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_4507756
loop_
_publ_author_name
'Sanphui, Palash'
'Babu, N. Jagadeesh'
'Nangia, Ashwini'
_publ_section_title
;
 Temozolomide Cocrystals with Carboxamide Coformers
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2208
_journal_paper_doi               10.1021/cg400322t
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C6 H6 N6 O2, C5 H5 N3 O'
_chemical_formula_sum            'C11 H11 N9 O3'
_chemical_formula_weight         317.29
_chemical_melting_point          462.5(15)
_chemical_name_systematic
; 
 1:1 cocrystal of Temozolomide and Pyrazinamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.398(2)
_cell_angle_beta                 89.951(2)
_cell_angle_gamma                63.129(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5570(11)
_cell_length_b                   9.2537(12)
_cell_length_c                   10.3924(14)
_cell_measurement_reflns_used    1999
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.68
_cell_volume                     668.77(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7002
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                1655
_reflns_number_total             2632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400322t_si_006.cif
_cod_data_source_block           TMZ-PYZ
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '461-464' was changed to '462.5(15)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507756
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.9588(3) -0.2281(2) 0.40125(19) 0.0578(5) Uani 1 1 d .
O2 O 0.8207(2) 0.5861(2) 0.14264(18) 0.0536(5) Uani 1 1 d .
N1 N 1.1350(3) -0.2708(3) 0.2431(3) 0.0531(7) Uani 1 1 d .
N2 N 1.0486(3) 0.0858(3) 0.1305(2) 0.0427(5) Uani 1 1 d .
N3 N 0.8892(2) 0.2978(2) 0.19901(19) 0.0383(5) Uani 1 1 d .
N4 N 0.7252(3) 0.4418(3) 0.3277(2) 0.0452(5) Uani 1 1 d .
N5 N 0.7135(3) 0.2939(3) 0.4144(2) 0.0470(5) Uani 1 1 d .
N6 N 0.7911(3) 0.1509(3) 0.3968(2) 0.0432(5) Uani 1 1 d .
C1 C 1.0250(3) -0.1721(3) 0.3039(2) 0.0415(6) Uani 1 1 d .
C6 C 0.6417(4) 0.5935(4) 0.3661(3) 0.0676(9) Uani 1 1 d .
H6A H 0.5866 0.5651 0.4453 0.101 Uiso 1 1 calc R
H6B H 0.5526 0.6952 0.2874 0.101 Uiso 1 1 calc R
H6C H 0.7310 0.6196 0.3906 0.101 Uiso 1 1 calc R
C5 C 0.8115(3) 0.4561(3) 0.2167(2) 0.0405(6) Uani 1 1 d .
C4 C 0.9893(3) 0.2533(3) 0.1047(3) 0.0437(6) Uani 1 1 d .
H4 H 1.0126 0.3313 0.0315 0.052 Uiso 1 1 calc R
C3 C 0.8848(3) 0.1466(3) 0.2898(2) 0.0356(6) Uani 1 1 d .
C2 C 0.9859(3) 0.0156(3) 0.2453(2) 0.0359(6) Uani 1 1 d .
O3 O 0.6095(2) 0.2852(2) -0.02723(18) 0.0599(6) Uani 1 1 d .
N8 N 0.4759(3) 0.0287(3) 0.2462(2) 0.0430(5) Uani 1 1 d .
N9 N 0.2940(3) 0.3492(3) 0.2763(2) 0.0550(6) Uani 1 1 d .
N7 N 0.6855(3) -0.0032(3) 0.0562(3) 0.0510(6) Uani 1 1 d .
C8 C 0.4834(3) 0.1745(3) 0.1633(2) 0.0376(6) Uani 1 1 d .
C7 C 0.5978(3) 0.1572(3) 0.0540(3) 0.0411(6) Uani 1 1 d .
C10 C 0.2870(3) 0.2042(4) 0.3585(3) 0.0510(7) Uani 1 1 d .
H10 H 0.2197 0.2092 0.4286 0.061 Uiso 1 1 calc R
C9 C 0.3944(3) 0.3314(3) 0.1772(3) 0.0488(7) Uani 1 1 d .
H9 H 0.4032 0.4292 0.1164 0.059 Uiso 1 1 calc R
C11 C 0.3761(3) 0.0467(3) 0.3436(3) 0.0497(7) Uani 1 1 d .
H11 H 0.3664 -0.0508 0.4037 0.060 Uiso 1 1 calc R
H7B H 0.665(4) -0.095(4) 0.121(3) 0.082(10) Uiso 1 1 d .
H7A H 0.757(4) -0.014(4) -0.009(3) 0.081(10) Uiso 1 1 d .
H1B H 1.178(4) -0.224(4) 0.174(3) 0.070(10) Uiso 1 1 d .
H1A H 1.158(3) -0.379(4) 0.270(3) 0.052(8) Uiso 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'
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
C1 N1 H1B 120.2(19)
C1 N1 H1A 119.1(17)
H1B N1 H1A 121(2)
C4 N2 C2 107.43(19)
C4 N3 C3 107.10(19)
C4 N3 C5 130.12(19)
C3 N3 C5 122.63(18)
C5 N4 N5 126.73(19)
C5 N4 C6 118.4(2)
N5 N4 C6 114.76(19)
N6 N5 N4 120.24(19)
N5 N6 C3 118.9(2)
O1 C1 N1 123.8(2)
O1 C1 C2 120.9(2)
N1 C1 C2 115.2(2)
N4 C6 H6A 109.5
N4 C6 H6B 109.5
H6A C6 H6B 109.5
N4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O2 C5 N4 125.8(2)
O2 C5 N3 123.5(2)
N4 C5 N3 110.72(19)
N2 C4 N3 110.9(2)
N2 C4 H4 124.6
N3 C4 H4 124.6
N6 C3 C2 133.6(2)
N6 C3 N3 120.6(2)
C2 C3 N3 105.72(18)
N2 C2 C3 108.9(2)
N2 C2 C1 122.5(2)
C3 C2 C1 128.67(19)
C11 N8 C8 115.5(2)
C10 N9 C9 115.4(2)
C7 N7 H7B 118.4(18)
C7 N7 H7A 115.6(19)
H7B N7 H7A 126(3)
N8 C8 C9 122.3(2)
N8 C8 C7 116.7(2)
C9 C8 C7 121.1(2)
O3 C7 N7 123.8(2)
O3 C7 C8 120.6(2)
N7 C7 C8 115.5(2)
N9 C10 C11 122.2(2)
N9 C10 H10 118.9
C11 C10 H10 118.9
N9 C9 C8 122.2(2)
N9 C9 H9 118.9
C8 C9 H9 118.9
N8 C11 C10 122.5(2)
N8 C11 H11 118.8
C10 C11 H11 118.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.222(3)
O2 C5 1.204(3)
N1 C1 1.329(3)
N1 H1B 0.87(3)
N1 H1A 0.86(3)
N2 C4 1.309(3)
N2 C2 1.370(3)
N3 C4 1.357(3)
N3 C3 1.387(3)
N3 C5 1.393(3)
N4 C5 1.367(3)
N4 N5 1.383(3)
N4 C6 1.464(3)
N5 N6 1.268(3)
N6 C3 1.372(3)
C1 C2 1.482(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C4 H4 0.9300
C3 C2 1.377(3)
O3 C7 1.223(3)
N8 C11 1.332(3)
N8 C8 1.338(3)
N9 C10 1.327(3)
N9 C9 1.350(3)
N7 C7 1.318(3)
N7 H7B 0.96(3)
N7 H7A 0.92(3)
C8 C9 1.365(3)
C8 C7 1.505(3)
C10 C11 1.375(4)
C10 H10 0.9300
C9 H9 0.9300
C11 H11 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652549
