#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/07/7200758.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_7200758
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Dimorphs of a 1 : 1 cocrystal of ethenzamide and
 saccharin: solid-state grinding methods result in metastable polymorph
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              889
_journal_paper_doi               10.1039/b821373a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         ' C9 H11 N O2, C7 H5 N O3 S'
_chemical_formula_sum            'C16 H16 N2 O5 S'
_chemical_formula_weight         348.37
_chemical_melting_point          394.34
_chemical_name_common
;
Form II of 1:1 cocrystal of ethenzamide and saccharin
;
_chemical_name_systematic
;
Form II of 1:1 cocrystal of ethenzamide and saccharin
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6125(17)
_cell_length_b                   16.607(3)
_cell_length_c                   11.183(2)
_cell_measurement_reflns_used    5455
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.0825
_cell_measurement_theta_min      2.1960
_cell_volume                     1599.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area deterctor'
_diffrn_measurement_method       'ω 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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12033
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9507
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0840P)²+0.6428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                3526
_reflns_number_total             3951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821373a.txt
_cod_data_source_block           EASACFII
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1598.9(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7200758
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
S1 S 0.79388(5) 0.13461(3) 0.61302(4) 0.02297(17) Uani 1 1 d . . .
O5 O 0.89417(18) 0.13275(9) 0.71728(13) 0.0301(3) Uani 1 1 d . . .
O2 O 0.68908(16) 0.25224(8) 0.29227(13) 0.0259(3) Uani 1 1 d . . .
O1 O 0.42636(18) 0.04262(9) 0.24510(13) 0.0328(4) Uani 1 1 d . . .
O3 O 0.70884(17) -0.05839(9) 0.45456(13) 0.0304(3) Uani 1 1 d . . .
C1 C 0.6079(2) 0.13832(11) 0.17672(18) 0.0220(4) Uani 1 1 d . . .
O4 O 0.67747(17) 0.19660(9) 0.60821(14) 0.0291(3) Uani 1 1 d . . .
N1 N 0.4925(2) 0.14135(11) 0.37444(16) 0.0262(4) Uani 1 1 d . . .
C2 C 0.8983(2) 0.13074(12) 0.48024(18) 0.0230(4) Uani 1 1 d . . .
N2 N 0.71371(19) 0.04548(10) 0.58961(15) 0.0246(4) Uani 1 1 d . . .
C3 C 0.8654(2) 0.05953(12) 0.42008(17) 0.0236(4) Uani 1 1 d . . .
C4 C 0.7003(2) 0.20822(12) 0.18952(17) 0.0230(4) Uani 1 1 d . . .
C5 C 0.9995(2) 0.18761(13) 0.43699(19) 0.0265(4) Uani 1 1 d . . .
H5 H 1.0193 0.2354 0.4781 0.032 Uiso 1 1 calc R . .
C6 C 0.8000(2) 0.22955(13) 0.09824(18) 0.0263(4) Uani 1 1 d . . .
H6 H 0.8619 0.2752 0.1065 0.032 Uiso 1 1 calc R . .
C7 C 0.5021(2) 0.10528(12) 0.26893(18) 0.0246(4) Uani 1 1 d . . .
C8 C 0.7552(2) 0.00753(12) 0.48538(17) 0.0241(4) Uani 1 1 d . . .
C9 C 0.7675(2) 0.32911(12) 0.2988(2) 0.0286(4) Uani 1 1 d . . .
H9A H 0.7366 0.3625 0.2311 0.034 Uiso 1 1 calc R . .
H9B H 0.8791 0.3215 0.2977 0.034 Uiso 1 1 calc R . .
C10 C 0.7156(3) 0.11475(13) -0.0193(2) 0.0314(5) Uani 1 1 d . . .
H10 H 0.7194 0.0840 -0.0886 0.038 Uiso 1 1 calc R . .
C11 C 0.9354(2) 0.04323(13) 0.31190(18) 0.0267(4) Uani 1 1 d . . .
H11 H 0.9133 -0.0040 0.2701 0.032 Uiso 1 1 calc R . .
C12 C 0.8074(2) 0.18309(13) -0.00509(19) 0.0298(5) Uani 1 1 d . . .
H12 H 0.8744 0.1979 -0.0652 0.036 Uiso 1 1 calc R . .
C13 C 0.6188(2) 0.09366(13) 0.07197(19) 0.0273(4) Uani 1 1 d . . .
H13 H 0.5581 0.0476 0.0631 0.033 Uiso 1 1 calc R . .
C14 C 1.0708(2) 0.17064(14) 0.32932(19) 0.0297(5) Uani 1 1 d . . .
H14 H 1.1404 0.2074 0.2981 0.036 Uiso 1 1 calc R . .
C15 C 1.0390(2) 0.09936(14) 0.26798(19) 0.0298(4) Uani 1 1 d . . .
H15 H 1.0880 0.0891 0.1964 0.036 Uiso 1 1 calc R . .
C16 C 0.7221(3) 0.36851(13) 0.4137(2) 0.0345(5) Uani 1 1 d . . .
H16A H 0.6130 0.3804 0.4105 0.052 Uiso 1 1 calc R . .
H16B H 0.7798 0.4175 0.4247 0.052 Uiso 1 1 calc R . .
H16C H 0.7446 0.3328 0.4794 0.052 Uiso 1 1 calc R . .
H1 H 0.553(3) 0.1826(15) 0.386(2) 0.026(6) Uiso 1 1 d . . .
H2 H 0.433(3) 0.1216(16) 0.432(3) 0.042(8) Uiso 1 1 d . . .
H3 H 0.662(4) 0.018(2) 0.645(3) 0.068(10) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 '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
_geom_angle_publ_flag
O5 S1 O4 116.81(9) . . ?
O5 S1 N2 110.52(9) . . ?
O4 S1 N2 110.34(9) . . ?
O5 S1 C2 112.07(9) . . ?
O4 S1 C2 111.49(9) . . ?
N2 S1 C2 93.11(9) . . ?
C4 O2 C9 118.13(16) . . ?
C13 C1 C4 118.28(18) . . ?
C13 C1 C7 116.05(17) . . ?
C4 C1 C7 125.62(18) . . ?
C7 N1 H1 116.0(17) . . ?
C7 N1 H2 121.7(18) . . ?
H1 N1 H2 122(2) . . ?
C5 C2 C3 122.46(19) . . ?
C5 C2 S1 127.76(16) . . ?
C3 C2 S1 109.78(14) . . ?
C8 N2 S1 115.28(14) . . ?
C8 N2 H3 120(2) . . ?
S1 N2 H3 124(2) . . ?
C2 C3 C11 119.99(18) . . ?
C2 C3 C8 112.46(17) . . ?
C11 C3 C8 127.54(19) . . ?
O2 C4 C6 122.45(18) . . ?
O2 C4 C1 118.23(17) . . ?
C6 C4 C1 119.32(19) . . ?
C2 C5 C14 117.4(2) . . ?
C2 C5 H5 121.3 . . ?
C14 C5 H5 121.3 . . ?
C12 C6 C4 120.55(19) . . ?
C12 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
O1 C7 N1 121.33(18) . . ?
O1 C7 C1 118.71(18) . . ?
N1 C7 C1 119.95(18) . . ?
O3 C8 N2 124.21(18) . . ?
O3 C8 C3 126.43(18) . . ?
N2 C8 C3 109.36(17) . . ?
O2 C9 C16 107.22(17) . . ?
O2 C9 H9A 110.3 . . ?
C16 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
C16 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C13 C10 C12 118.4(2) . . ?
C13 C10 H10 120.8 . . ?
C12 C10 H10 120.8 . . ?
C15 C11 C3 118.2(2) . . ?
C15 C11 H11 120.9 . . ?
C3 C11 H11 120.9 . . ?
C10 C12 C6 120.62(19) . . ?
C10 C12 H12 119.7 . . ?
C6 C12 H12 119.7 . . ?
C10 C13 C1 122.8(2) . . ?
C10 C13 H13 118.6 . . ?
C1 C13 H13 118.6 . . ?
C15 C14 C5 120.82(19) . . ?
C15 C14 H14 119.6 . . ?
C5 C14 H14 119.6 . . ?
C11 C15 C14 121.1(2) . . ?
C11 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4337(16) . ?
S1 O4 1.4370(15) . ?
S1 N2 1.6512(18) . ?
S1 C2 1.757(2) . ?
O2 C4 1.367(2) . ?
O2 C9 1.445(2) . ?
O1 C7 1.253(2) . ?
O3 C8 1.212(2) . ?
C1 C13 1.392(3) . ?
C1 C4 1.412(3) . ?
C1 C7 1.498(3) . ?
N1 C7 1.328(3) . ?
N1 H1 0.87(3) . ?
N1 H2 0.90(3) . ?
C2 C5 1.381(3) . ?
C2 C3 1.386(3) . ?
N2 C8 1.380(3) . ?
N2 H3 0.90(3) . ?
C3 C11 1.392(3) . ?
C3 C8 1.488(3) . ?
C4 C6 1.396(3) . ?
C5 C14 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C12 1.392(3) . ?
C6 H6 0.9300 . ?
C9 C16 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.380(3) . ?
C10 C12 1.390(3) . ?
C10 H10 0.9300 . ?
C11 C15 1.389(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653571
