#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/07/7200757.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_7200757
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          395.57
_chemical_name_common
;
Form I of 1:1 cocrystal of ethenzamide and saccharin
;
_chemical_name_systematic
;
Form I of 1:1 cocrystal of ethenzamide 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                85.14(3)
_cell_angle_beta                 86.43(3)
_cell_angle_gamma                70.65(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2141(14)
_cell_length_b                   7.4923(15)
_cell_length_c                   15.456(3)
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.9526
_cell_measurement_theta_min      2.6468
_cell_volume                     784.9(3)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Saturn 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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10878
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9542
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0381
_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)+(0.0457P)²+0.4596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                3707
_reflns_number_total             3823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821373a.txt
_cod_data_source_block           EASACFI
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        784.8(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200757
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
S1 S 0.14065(5) 0.21941(4) 0.34324(2) 0.01944(9) Uani 1 1 d . . .
O3 O 0.20291(15) 0.67494(14) 0.39190(7) 0.0258(2) Uani 1 1 d . . .
O5 O -0.05627(15) 0.21497(14) 0.34012(7) 0.0259(2) Uani 1 1 d . . .
O4 O 0.28746(16) 0.09552(14) 0.28911(6) 0.0267(2) Uani 1 1 d . . .
N2 N 0.14295(18) 0.43899(16) 0.32513(8) 0.0225(2) Uani 1 1 d . . .
C16 C 0.21408(18) 0.20163(18) 0.45059(8) 0.0181(2) Uani 1 1 d . . .
C15 C 0.24222(18) 0.36914(18) 0.46880(8) 0.0187(2) Uani 1 1 d . . .
C12 C 0.30785(19) 0.0656(2) 0.59124(9) 0.0227(3) Uani 1 1 d . . .
H12 H 0.3299 -0.0347 0.6333 0.027 Uiso 1 1 calc R . .
C11 C 0.3402(2) 0.2311(2) 0.61041(9) 0.0238(3) Uani 1 1 d . . .
H11 H 0.3850 0.2384 0.6647 0.029 Uiso 1 1 calc R . .
C14 C 0.19659(19) 0.51446(18) 0.39406(8) 0.0204(2) Uani 1 1 d . . .
C13 C 0.24328(19) 0.04718(18) 0.51049(8) 0.0205(2) Uani 1 1 d . . .
H13 H 0.2210 -0.0627 0.4974 0.025 Uiso 1 1 calc R . .
C10 C 0.30669(19) 0.38602(19) 0.54972(9) 0.0219(3) Uani 1 1 d . . .
H10 H 0.3268 0.4969 0.5629 0.026 Uiso 1 1 calc R . .
O1 O 1.05749(17) -0.38247(14) 0.17163(6) 0.0290(2) Uani 1 1 d . . .
O2 O 0.71642(14) 0.18529(13) 0.13330(6) 0.0225(2) Uani 1 1 d . . .
N1 N 0.96896(18) -0.09755(17) 0.22766(7) 0.0223(2) Uani 1 1 d . . .
C7 C 0.96863(19) -0.20750(18) 0.16474(8) 0.0193(2) Uani 1 1 d . . .
C6 C 0.8966(2) -0.24455(18) 0.01591(8) 0.0216(3) Uani 1 1 d . . .
H6 H 0.9739 -0.3707 0.0260 0.026 Uiso 1 1 calc R . .
C1 C 0.86507(18) -0.12237(17) 0.08292(8) 0.0181(2) Uani 1 1 d . . .
C5 C 0.8169(2) -0.1843(2) -0.06499(9) 0.0228(3) Uani 1 1 d . . .
H5 H 0.8406 -0.2682 -0.1086 0.027 Uiso 1 1 calc R . .
C4 C 0.7008(2) 0.0041(2) -0.07960(8) 0.0224(3) Uani 1 1 d . . .
H4 H 0.6459 0.0466 -0.1335 0.027 Uiso 1 1 calc R . .
C3 C 0.66597(19) 0.12918(19) -0.01468(9) 0.0217(3) Uani 1 1 d . . .
H3 H 0.5880 0.2549 -0.0254 0.026 Uiso 1 1 calc R . .
C2 C 0.74715(18) 0.06793(18) 0.06685(8) 0.0184(2) Uani 1 1 d . . .
C8 C 0.5996(2) 0.38156(19) 0.11780(9) 0.0249(3) Uani 1 1 d . . .
H8A H 0.4678 0.3922 0.1025 0.030 Uiso 1 1 calc R . .
H8B H 0.6582 0.4407 0.0705 0.030 Uiso 1 1 calc R . .
C9 C 0.5932(2) 0.4766(2) 0.20073(11) 0.0324(3) Uani 1 1 d . . .
H9A H 0.5444 0.4106 0.2479 0.049 Uiso 1 1 calc R . .
H9B H 0.5080 0.6057 0.1944 0.049 Uiso 1 1 calc R . .
H9C H 0.7232 0.4738 0.2127 0.049 Uiso 1 1 calc R . .
H1B H 0.912(3) 0.022(3) 0.2202(13) 0.034(5) Uiso 1 1 d . . .
H2 H 0.118(3) 0.502(3) 0.2701(16) 0.053(6) Uiso 1 1 d . . .
H1A H 1.039(3) -0.153(3) 0.2759(14) 0.039(5) 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
O4 S1 O5 116.91(7) . . ?
O4 S1 N2 110.20(7) . . ?
O5 S1 N2 110.26(7) . . ?
O4 S1 C16 112.27(7) . . ?
O5 S1 C16 111.52(7) . . ?
N2 S1 C16 93.17(7) . . ?
C14 N2 S1 115.55(10) . . ?
C14 N2 H2 123.8(14) . . ?
S1 N2 H2 120.5(14) . . ?
C13 C16 C15 123.13(12) . . ?
C13 C16 S1 127.16(10) . . ?
C15 C16 S1 109.71(10) . . ?
C16 C15 C10 120.02(12) . . ?
C16 C15 C14 112.50(11) . . ?
C10 C15 C14 127.48(12) . . ?
C13 C12 C11 121.47(13) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C11 C10 121.25(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O3 C14 N2 123.84(13) . . ?
O3 C14 C15 127.12(12) . . ?
N2 C14 C15 109.04(11) . . ?
C16 C13 C12 116.35(12) . . ?
C16 C13 H13 121.8 . . ?
C12 C13 H13 121.8 . . ?
C15 C10 C11 117.76(13) . . ?
C15 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C2 O2 C8 118.48(11) . . ?
C7 N1 H1B 119.3(13) . . ?
C7 N1 H1A 118.0(13) . . ?
H1B N1 H1A 122.5(18) . . ?
O1 C7 N1 121.26(12) . . ?
O1 C7 C1 118.73(12) . . ?
N1 C7 C1 119.99(12) . . ?
C5 C6 C1 122.32(12) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C6 C1 C2 118.21(12) . . ?
C6 C1 C7 115.62(11) . . ?
C2 C1 C7 126.12(12) . . ?
C6 C5 C4 118.62(12) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C3 C4 C5 120.68(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 120.53(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C2 C3 122.88(12) . . ?
O2 C2 C1 117.49(11) . . ?
C3 C2 C1 119.63(12) . . ?
O2 C8 C9 107.01(12) . . ?
O2 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 O4 1.4328(12) . ?
S1 O5 1.4358(11) . ?
S1 N2 1.6507(12) . ?
S1 C16 1.7540(13) . ?
O3 C14 1.2158(17) . ?
N2 C14 1.3794(17) . ?
N2 H2 0.93(2) . ?
C16 C13 1.3863(18) . ?
C16 C15 1.3897(18) . ?
C15 C10 1.3909(18) . ?
C15 C14 1.4917(19) . ?
C12 C13 1.3922(19) . ?
C12 C11 1.394(2) . ?
C12 H12 0.9300 . ?
C11 C10 1.394(2) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
O1 C7 1.2525(16) . ?
O2 C2 1.3684(15) . ?
O2 C8 1.4402(16) . ?
N1 C7 1.3272(17) . ?
N1 H1B 0.85(2) . ?
N1 H1A 0.92(2) . ?
C7 C1 1.4932(18) . ?
C6 C5 1.3855(19) . ?
C6 C1 1.3985(17) . ?
C6 H6 0.9300 . ?
C1 C2 1.4074(18) . ?
C5 C4 1.389(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.3856(19) . ?
C4 H4 0.9300 . ?
C3 C2 1.3991(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.509(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653571
