#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/26/4502682.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_4502682
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Polymorphs and Solvates of a Cocrystal Involving an Analgesic Drug,
 Ethenzamide, and 3,5-Dinitrobenzoic Acid
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2229
_journal_paper_doi               10.1021/cg9015178
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C9 H11 N O2, C7 H4 N2 O6'
_chemical_formula_sum            'C16 H15 N3 O8'
_chemical_formula_weight         377.31
_chemical_name_common
;
Acetonitrile solvate of 1:1 cocrystal of 
ethenzamide and 3,5-dinitrobenzoic acid
;
_chemical_name_systematic
;
Acetonitrile solvate of 1:1 cocrystal of 
ethenzamide and 3,5-dinitrobenzoic acid
;
_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                74.952(15)
_cell_angle_beta                 82.419(15)
_cell_angle_gamma                80.051(17)
_cell_formula_units_Z            2
_cell_length_a                   7.663(3)
_cell_length_b                   8.193(3)
_cell_length_c                   15.830(6)
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.9829
_cell_measurement_theta_min      2.6212
_cell_volume                     941.4(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0563
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14549
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.066
_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     257
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0804
_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)+(0.0938P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                3555
_reflns_number_total             5355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9015178_si_001.cif
_cod_data_source_block           EA+DNBA-Acetonitrile
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4502682
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
O2 O 0.3497(2) 0.09172(19) 0.38684(10) 0.0315(4) Uani 1 1 d .
O1 O 0.1106(2) 0.5893(2) 0.38538(10) 0.0359(4) Uani 1 1 d .
O8 O -0.1031(2) 1.1045(2) 0.71672(11) 0.0385(4) Uani 1 1 d .
O3 O 0.1012(2) 1.0325(2) 0.61207(11) 0.0420(4) Uani 1 1 d .
N2 N 0.2353(3) 0.3835(3) 0.70820(13) 0.0353(5) Uani 1 1 d .
N1 N 0.1521(3) 0.3198(3) 0.46500(13) 0.0344(5) Uani 1 1 d .
C1 C -0.0715(3) 0.6003(3) 0.85973(14) 0.0300(5) Uani 1 1 d .
O6 O -0.1583(3) 0.4038(2) 0.98519(12) 0.0482(5) Uani 1 1 d .
O4 O 0.3091(2) 0.4253(2) 0.63375(11) 0.0448(5) Uani 1 1 d .
O7 O -0.2672(3) 0.6701(3) 0.97437(12) 0.0501(5) Uani 1 1 d .
C2 C 0.0305(3) 0.4702(3) 0.82744(14) 0.0308(5) Uani 1 1 d .
H2 H 0.0372 0.3543 0.8596 0.037 Uiso 1 1 calc R
C3 C 0.1167(3) 0.6853(3) 0.69788(14) 0.0291(5) Uani 1 1 d .
H3 H 0.1818 0.7128 0.6419 0.035 Uiso 1 1 calc R
C4 C 0.0133(3) 0.8142(3) 0.73325(13) 0.0291(5) Uani 1 1 d .
O5 O 0.2494(3) 0.2376(2) 0.75462(12) 0.0488(5) Uani 1 1 d .
C5 C 0.5132(3) 0.1921(3) 0.24601(15) 0.0326(5) Uani 1 1 d .
H5A H 0.5652 0.0787 0.2445 0.039 Uiso 1 1 calc R
C6 C 0.3180(3) 0.3906(3) 0.32044(14) 0.0291(5) Uani 1 1 d .
C7 C 0.1879(3) 0.4387(3) 0.39305(14) 0.0302(5) Uani 1 1 d .
C8 C 0.3952(3) 0.2227(3) 0.31822(14) 0.0282(5) Uani 1 1 d .
C9 C -0.0819(3) 0.7710(3) 0.81520(14) 0.0302(5) Uani 1 1 d .
H9 H -0.1527 0.8570 0.8401 0.036 Uiso 1 1 calc R
N3 N -0.1731(3) 0.5549(3) 0.94576(13) 0.0397(5) Uani 1 1 d .
C10 C 0.1228(3) 0.5170(3) 0.74555(14) 0.0304(5) Uani 1 1 d .
C11 C 0.4410(3) -0.0799(3) 0.39009(15) 0.0328(5) Uani 1 1 d .
H11A H 0.5708 -0.0837 0.3903 0.039 Uiso 1 1 calc R
H11B H 0.4193 -0.1179 0.3384 0.039 Uiso 1 1 calc R
C12 C 0.0095(3) 0.9939(3) 0.68036(15) 0.0311(5) Uani 1 1 d .
C13 C 0.3678(3) -0.1933(3) 0.47357(15) 0.0354(5) Uani 1 1 d .
H13A H 0.3903 -0.1543 0.5241 0.053 Uiso 1 1 calc R
H13B H 0.4260 -0.3113 0.4784 0.053 Uiso 1 1 calc R
H13C H 0.2393 -0.1881 0.4725 0.053 Uiso 1 1 calc R
C14 C 0.3635(3) 0.5231(3) 0.24949(14) 0.0331(5) Uani 1 1 d .
H14 H 0.3132 0.6373 0.2500 0.040 Uiso 1 1 calc R
C15 C 0.4799(3) 0.4933(3) 0.17827(15) 0.0371(6) Uani 1 1 d .
H15 H 0.5088 0.5856 0.1309 0.045 Uiso 1 1 calc R
C16 C 0.5529(3) 0.3274(3) 0.17735(15) 0.0362(5) Uani 1 1 d .
H16 H 0.6318 0.3059 0.1286 0.043 Uiso 1 1 calc R
H1 H 0.075(3) 0.345(3) 0.5116(18) 0.039(7) Uiso 1 1 d .
H8 H -0.110(5) 1.225(5) 0.683(3) 0.090(12) Uiso 1 1 d .
H2A H 0.206(4) 0.209(5) 0.471(2) 0.066(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 0.0016 '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
C8 O2 C11 118.98(17)
C12 O8 H8 115(2)
O5 N2 O4 124.7(2)
O5 N2 C10 117.0(2)
O4 N2 C10 118.4(2)
C7 N1 H1 122.1(16)
C7 N1 H2A 121(2)
H1 N1 H2A 117(3)
C2 C1 C9 123.2(2)
C2 C1 N3 118.0(2)
C9 C1 N3 118.8(2)
C1 C2 C10 116.6(2)
C1 C2 H2 121.7
C10 C2 H2 121.7
C10 C3 C4 119.1(2)
C10 C3 H3 120.5
C4 C3 H3 120.5
C9 C4 C3 119.5(2)
C9 C4 C12 122.7(2)
C3 C4 C12 117.80(19)
C16 C5 C8 119.8(2)
C16 C5 H5A 120.1
C8 C5 H5A 120.1
C14 C6 C8 117.8(2)
C14 C6 C7 117.3(2)
C8 C6 C7 125.0(2)
O1 C7 N1 119.7(2)
O1 C7 C6 120.7(2)
N1 C7 C6 119.5(2)
O2 C8 C6 118.24(19)
O2 C8 C5 121.6(2)
C6 C8 C5 120.2(2)
C1 C9 C4 118.9(2)
C1 C9 H9 120.6
C4 C9 H9 120.6
O6 N3 O7 123.8(2)
O6 N3 C1 117.8(2)
O7 N3 C1 118.4(2)
C3 C10 C2 122.7(2)
C3 C10 N2 118.3(2)
C2 C10 N2 118.9(2)
O2 C11 C13 106.73(18)
O2 C11 H11A 110.4
C13 C11 H11A 110.4
O2 C11 H11B 110.4
C13 C11 H11B 110.4
H11A C11 H11B 108.6
O3 C12 O8 124.5(2)
O3 C12 C4 122.6(2)
O8 C12 C4 112.86(19)
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 C6 122.2(2)
C15 C14 H14 118.9
C6 C14 H14 118.9
C16 C15 C14 119.0(2)
C16 C15 H15 120.5
C14 C15 H15 120.5
C15 C16 C5 121.2(2)
C15 C16 H16 119.4
C5 C16 H16 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.370(3)
O2 C11 1.450(3)
O1 C7 1.256(3)
O8 C12 1.329(3)
O8 H8 0.99(4)
O3 C12 1.209(3)
N2 O5 1.225(3)
N2 O4 1.228(3)
N2 C10 1.472(3)
N1 C7 1.325(3)
N1 H1 0.93(3)
N1 H2A 0.91(3)
C1 C2 1.378(3)
C1 C9 1.386(3)
C1 N3 1.469(3)
O6 N3 1.226(3)
O7 N3 1.231(3)
C2 C10 1.386(3)
C2 H2 0.9500
C3 C10 1.385(3)
C3 C4 1.399(3)
C3 H3 0.9500
C4 C9 1.393(3)
C4 C12 1.491(3)
C5 C16 1.381(3)
C5 C8 1.409(3)
C5 H5A 0.9500
C6 C14 1.399(3)
C6 C8 1.408(3)
C6 C7 1.506(3)
C9 H9 0.9500
C11 C13 1.507(3)
C11 H11A 0.9900
C11 H11B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.389(3)
C14 H14 0.9500
C15 C16 1.380(4)
C15 H15 0.9500
C16 H16 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144995
