#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:06:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179613 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/77/4507757.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_4507757
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         '2(C6 H6 N6 O2), C7 H5 N O3 S'
_chemical_formula_sum            'C19 H17 N13 O7 S'
_chemical_formula_weight         571.52
_chemical_melting_point          495.5(15)
_chemical_name_systematic
; 
  2:1 cocrystal of Temzolomide and Saccharin  
;
_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                76.591(7)
_cell_angle_beta                 75.856(7)
_cell_angle_gamma                87.095(7)
_cell_formula_units_Z            1
_cell_length_a                   6.521(3)
_cell_length_b                   8.064(4)
_cell_length_c                   11.952(5)
_cell_measurement_reflns_used    2102
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.60
_cell_volume                     592.8(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5706
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       diamond
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.1546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                1471
_reflns_number_total             2086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400322t_si_007.cif
_cod_data_source_block           TMZ-SAC
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '494-497' was changed to '495.5(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               4507757
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.3125(3) 0.3336(2) 0.55767(16) 0.0627(6) Uani 1 1 d . . .
O2 O 0.5378(3) 0.1417(2) 0.32034(16) 0.0606(5) Uani 1 1 d . . .
N3 N 0.8115(3) 0.2365(2) 0.37887(16) 0.0401(5) Uani 1 1 d . . .
C3 C 0.9880(3) 0.3394(3) 0.3485(2) 0.0409(6) Uani 1 1 d . . .
N1 N 1.3571(4) 0.5090(3) 0.3779(2) 0.0510(6) Uani 1 1 d . . .
N6 N 1.0492(3) 0.4459(3) 0.23882(19) 0.0569(6) Uani 1 1 d . . .
N2 N 0.9470(3) 0.1897(3) 0.53507(17) 0.0466(5) Uani 1 1 d . . .
C1 C 1.2558(4) 0.3850(3) 0.4651(2) 0.0457(6) Uani 1 1 d . . .
C5 C 0.6886(4) 0.2333(3) 0.2994(2) 0.0451(6) Uani 1 1 d . . .
N4 N 0.7621(3) 0.3489(3) 0.19442(18) 0.0523(6) Uani 1 1 d . . .
C2 C 1.0706(3) 0.3085(3) 0.4460(2) 0.0400(6) Uani 1 1 d . . .
C4 C 0.7947(4) 0.1489(3) 0.4934(2) 0.0454(6) Uani 1 1 d . . .
H4 H 0.6883 0.0703 0.5359 0.055 Uiso 1 1 calc R . .
C6 C 0.6463(5) 0.3705(4) 0.1012(3) 0.0767(9) Uani 1 1 d . . .
H6A H 0.6445 0.2646 0.0778 0.115 Uiso 1 1 calc R . .
H6B H 0.7148 0.4565 0.0341 0.115 Uiso 1 1 calc R . .
H6C H 0.5039 0.4045 0.1307 0.115 Uiso 1 1 calc R . .
N5 N 0.9382(3) 0.4515(3) 0.16424(19) 0.0630(7) Uani 1 1 d . . .
O3 O 0.4083(6) 0.2426(5) 0.8043(3) 0.0705(11) Uani 0.50 1 d P B .
C7 C 0.2380(8) 0.1724(7) 0.8405(5) 0.0499(13) Uani 0.50 1 d P . .
O4 O -0.2945(5) 0.1766(4) 0.8415(3) 0.0605(10) Uani 0.50 1 d P B .
S1 S -0.1228(2) 0.0584(3) 0.84328(15) 0.0430(4) Uani 0.50 1 d P . .
O5 O -0.1412(6) -0.0956(6) 0.8087(4) 0.0679(11) Uani 0.50 1 d P B .
H1A H 1.468(5) 0.568(3) 0.392(2) 0.073(9) Uiso 1 1 d . . .
H1B H 1.307(5) 0.547(4) 0.317(3) 0.072(10) Uiso 1 1 d . . .
C12 C -0.1255(16) 0.0151(16) 0.8273(8) 0.100(6) Uani 0.50 1 d PDU . .
H12 H -0.1844 0.0252 0.7626 0.120 Uiso 0.50 1 calc PR A 2
N7 N 0.1035(8) 0.1567(7) 0.7737(5) 0.0569(14) Uani 0.50 1 d P B 1
H7 H 0.1346 0.1962 0.6982 0.068 Uiso 0.50 1 calc PR B 1
C11 C 0.0720(13) 0.0858(9) 0.8134(6) 0.066(3) Uani 0.50 1 d PDU C 2
H11 H 0.1436 0.1461 0.7390 0.079 Uiso 0.50 1 calc PR C 2
C8 C 0.1451(7) 0.0880(6) 0.9651(5) 0.0409(12) Uani 0.50 1 d PD . 2
C9 C -0.0547(6) 0.0204(6) 0.9810(5) 0.0442(13) Uani 0.50 1 d PD . 2
C13 C -0.2326(9) -0.0704(7) 0.9392(5) 0.0622(15) Uani 0.50 1 d PDU . .
H13 H -0.3657 -0.1167 0.9498 0.075 Uiso 0.50 1 calc PR . .
C10 C 0.1641(11) 0.0676(9) 0.9094(6) 0.057(2) Uani 0.50 1 d PDU . .
H10 H 0.2967 0.1140 0.8995 0.069 Uiso 0.50 1 calc PR C 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 0.0000 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'
S S 0.1246 0.1234 '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
C4 N3 C3 106.60(19) . .
C4 N3 C5 131.5(2) . .
C3 N3 C5 121.9(2) . .
C2 C3 N6 132.3(2) . .
C2 C3 N3 106.1(2) . .
N6 C3 N3 121.6(2) . .
N5 N6 C3 118.9(2) . .
C4 N2 C2 106.8(2) . .
O1 C1 N1 122.6(2) . .
O1 C1 C2 120.4(2) . .
N1 C1 C2 117.1(2) . .
O2 C5 N4 124.7(2) . .
O2 C5 N3 124.3(2) . .
N4 C5 N3 111.0(2) . .
C5 N4 N5 127.0(2) . .
C5 N4 C6 119.0(2) . .
N5 N4 C6 113.9(2) . .
C3 C2 N2 109.3(2) . .
C3 C2 C1 129.9(2) . .
N2 C2 C1 120.8(2) . .
N2 C4 N3 111.3(2) . .
N6 N5 N4 119.6(2) . .
O3 C7 N7 125.6(5) . .
O3 C7 C8 125.1(5) . .
N7 C7 C8 109.2(5) . .
O5 S1 O4 117.8(2) . .
O5 S1 N7 112.1(3) . .
O4 S1 N7 110.3(3) . .
O5 S1 C9 111.5(3) . .
O4 S1 C9 110.2(3) . .
N7 S1 C9 91.9(2) . .
O5 S1 C8 90.8(2) . 2_557
O4 S1 C8 108.9(2) . 2_557
N7 S1 C8 115.9(2) . 2_557
C9 S1 C8 26.5(2) . 2_557
C13 C12 C11 118.8(9) . .
C7 N7 S1 116.9(4) . .
C12 C11 C10 121.0(8) . .
C9 C8 C13 83.1(5) 2_557 2_557
C9 C8 C9 42.6(5) 2_557 .
C13 C8 C9 119.6(5) 2_557 .
C9 C8 C7 142.4(6) 2_557 .
C13 C8 C7 127.9(4) 2_557 .
C9 C8 C7 112.4(5) . .
C9 C8 S1 47.7(4) 2_557 2_557
C13 C8 S1 35.7(3) 2_557 2_557
C9 C8 S1 85.1(4) . 2_557
C7 C8 S1 160.1(3) . 2_557
C9 C9 C8 87.5(6) 2_557 2_557
C9 C9 C10 77.5(7) 2_557 2_557
C8 C9 C10 30.2(4) 2_557 2_557
C9 C9 C8 49.8(5) 2_557 .
C8 C9 C8 137.4(5) 2_557 .
C10 C9 C8 121.0(5) 2_557 .
C9 C9 S1 142.9(8) 2_557 .
C8 C9 S1 105.7(5) 2_557 .
C10 C9 S1 129.5(4) 2_557 .
C8 C9 S1 109.4(4) . .
C8 C13 C12 120.9(7) 2_557 .
C8 C13 C10 12.9(3) 2_557 2_557
C12 C13 C10 126.6(6) . 2_557
C9 C10 C11 118.7(6) 2_557 .
C9 C10 C13 55.0(3) 2_557 2_557
C11 C10 C13 166.2(6) . 2_557
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.226(3) .
O2 C5 1.201(3) .
N3 C4 1.367(3) .
N3 C3 1.378(3) .
N3 C5 1.389(3) .
C3 C2 1.368(3) .
C3 N6 1.368(3) .
N1 C1 1.330(3) .
N6 N5 1.270(3) .
N2 C4 1.302(3) .
N2 C2 1.373(3) .
C1 C2 1.473(3) .
C5 N4 1.372(3) .
N4 N5 1.374(3) .
N4 C6 1.466(3) .
O3 C7 1.207(6) .
C7 N7 1.351(7) .
C7 C8 1.476(7) .
O4 S1 1.434(4) .
S1 O5 1.416(6) .
S1 N7 1.646(5) .
S1 C9 1.763(5) .
S1 C8 2.293(6) 2_557
C12 C13 1.385(5) .
C12 C11 1.392(5) .
C11 C10 1.396(5) .
C8 C9 1.064(7) 2_557
C8 C13 1.374(8) 2_557
C8 C9 1.391(4) .
C8 S1 2.293(6) 2_557
C9 C9 0.943(8) 2_557
C9 C8 1.064(7) 2_557
C9 C10 1.375(8) 2_557
C13 C8 1.374(8) 2_557
C13 C10 1.972(8) 2_557
C10 C9 1.375(8) 2_557
C10 C13 1.972(8) 2_557
