#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:56:18 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241531.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_7241531
loop_
_publ_author_name
'Mannava, M. K. Chaitanya'
'Gunnam, Anilkumar'
'Lodagekar, Anurag'
'Shastri, Nalini R.'
'Nangia, Ashwini K.'
'Solomon, K. Anand'
_publ_section_title
;
 Enhanced solubility, permeability, and tabletability of nicorandil by
 salt and cocrystal formation
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              227
_journal_page_last               237
_journal_paper_doi               10.1039/D0CE01316A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C8 H10 N3 O4, C4 H3 O4'
_chemical_formula_sum            'C12 H13 N3 O8'
_chemical_formula_weight         327.25
_chemical_melting_point          382.55
_chemical_name_common            'Nicorandil-Fumaric acid salt'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-08-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-08-30 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   29.813(6)
_cell_length_b                   4.787(2)
_cell_length_c                   9.861(2)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      3.42
_cell_volume                     1407.3(7)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7162
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_min         3.427
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2245
_reflns_number_total             2353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01316a2.cif
_cod_data_source_block           NCR_FA
_cod_depositor_comments
'Adding full bibliography for 7241531--7241532.cif.'
_cod_original_cell_volume        1407.2(7)
_cod_database_code               7241531
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C11(H11), C3(H3), C10(H10), C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.61998(6) 0.2158(3) 0.08875(18) 0.0427(4) Uani 1 1 d . . . . .
O8 O 0.79107(6) 0.3753(5) 0.9084(2) 0.0634(6) Uani 1 1 d . . . . .
O5 O 0.63823(6) 0.0422(4) 0.7610(2) 0.0575(6) Uani 1 1 d . . . . .
O6 O 0.68325(6) -0.1733(5) 0.6209(2) 0.0636(6) Uani 1 1 d . . . . .
O1 O 0.55027(6) 0.0174(4) 0.3248(2) 0.0588(5) Uani 1 1 d . . . . .
O4 O 0.59164(8) -0.1792(4) 0.0067(2) 0.0673(6) Uani 1 1 d . . . . .
O7 O 0.74398(6) 0.6300(4) 1.0289(2) 0.0589(5) Uani 1 1 d . . . . .
N1 N 0.58265(6) 0.6715(5) 0.6654(2) 0.0404(5) Uani 1 1 d . . . . .
N3 N 0.58791(7) 0.0675(5) 0.0148(2) 0.0454(5) Uani 1 1 d . . . . .
O3 O 0.55951(7) 0.2126(5) -0.0320(3) 0.0676(6) Uani 1 1 d . . . . .
N2 N 0.62289(7) 0.0716(5) 0.3760(2) 0.0424(5) Uani 1 1 d . . . . .
C1 C 0.59604(8) 0.5019(5) 0.5660(3) 0.0374(5) Uani 1 1 d . . . . .
H1A H 0.625424 0.512618 0.534758 0.045 Uiso 1 1 calc R U . . .
C2 C 0.56712(7) 0.3117(5) 0.5091(2) 0.0350(5) Uani 1 1 d . . . . .
C11 C 0.71305(7) 0.3220(5) 0.8727(3) 0.0397(6) Uani 1 1 d . . . . .
H11 H 0.684931 0.389636 0.897005 0.048 Uiso 1 1 calc R U . . .
C6 C 0.57947(8) 0.1215(5) 0.3948(3) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.52393(8) 0.2995(5) 0.5601(3) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.503494 0.173542 0.523496 0.054 Uiso 1 1 calc R U . . .
C12 C 0.75344(8) 0.4433(5) 0.9376(3) 0.0403(6) Uani 1 1 d . . . . .
C10 C 0.71572(8) 0.1236(5) 0.7829(3) 0.0424(6) Uani 1 1 d . . . . .
H10 H 0.744150 0.061765 0.758229 0.051 Uiso 1 1 calc R U . . .
C9 C 0.67669(7) -0.0102(5) 0.7173(3) 0.0391(5) Uani 1 1 d . . . . .
C8 C 0.65459(8) 0.0432(6) 0.1478(3) 0.0471(6) Uani 1 1 d . . . . .
H8A H 0.679861 0.160424 0.172345 0.056 Uiso 1 1 calc R U . . .
H8B H 0.664864 -0.089751 0.080434 0.056 Uiso 1 1 calc R U . . .
C5 C 0.54121(8) 0.6599(6) 0.7149(3) 0.0458(6) Uani 1 1 d . . . . .
H5 H 0.532765 0.780387 0.784342 0.055 Uiso 1 1 calc R U . . .
C7 C 0.63925(9) -0.1127(6) 0.2708(3) 0.0463(6) Uani 1 1 d . . . . .
H7A H 0.615551 -0.241114 0.245114 0.056 Uiso 1 1 calc R U . . .
H7B H 0.664029 -0.222024 0.306111 0.056 Uiso 1 1 calc R U . . .
C4 C 0.51098(8) 0.4724(6) 0.6647(3) 0.0500(7) Uani 1 1 d . . . . .
H4 H 0.482154 0.461639 0.700352 0.060 Uiso 1 1 calc R U . . .
H7 H 0.7723(12) 0.713(8) 1.066(4) 0.097(13) Uiso 1 1 d . . . . .
H2 H 0.6405(10) 0.136(6) 0.425(3) 0.048(8) Uiso 1 1 d . . . . .
H1 H 0.6058(10) 0.827(7) 0.699(4) 0.075(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O2 C8 114.14(19) . . ?
C12 O7 H7 110(2) . . ?
C1 N1 H1 117.3(19) . . ?
C5 N1 C1 121.5(2) . . ?
C5 N1 H1 121.1(19) . . ?
O4 N3 O2 118.4(2) . . ?
O3 N3 O2 113.2(2) . . ?
O3 N3 O4 128.4(2) . . ?
C6 N2 C7 122.5(2) . . ?
C6 N2 H2 120(2) . . ?
C7 N2 H2 117(2) . . ?
N1 C1 H1A 119.5 . . ?
N1 C1 C2 121.0(2) . . ?
C2 C1 H1A 119.5 . . ?
C1 C2 C6 123.8(2) . . ?
C1 C2 C3 117.6(2) . . ?
C3 C2 C6 118.5(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.0(2) . . ?
O1 C6 N2 122.9(3) . . ?
O1 C6 C2 120.0(2) . . ?
N2 C6 C2 117.0(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
O8 C12 O7 123.7(2) . . ?
O8 C12 C11 123.2(2) . . ?
O7 C12 C11 113.1(2) . . ?
C11 C10 H10 117.8 . . ?
C11 C10 C9 124.5(2) . . ?
C9 C10 H10 117.8 . . ?
O5 C9 C10 119.0(2) . . ?
O6 C9 O5 122.2(2) . . ?
O6 C9 C10 118.8(2) . . ?
O2 C8 H8A 108.9 . . ?
O2 C8 H8B 108.9 . . ?
O2 C8 C7 113.22(19) . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
N1 C5 H5 119.7 . . ?
N1 C5 C4 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
N2 C7 C8 112.3(2) . . ?
N2 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
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
O2 N3 1.396(3) . ?
O2 C8 1.444(3) . ?
O8 C12 1.203(3) . ?
O5 C9 1.250(3) . ?
O6 C9 1.246(3) . ?
O1 C6 1.218(3) . ?
O4 N3 1.189(3) . ?
O7 C12 1.300(3) . ?
O7 H7 1.00(4) . ?
N1 C1 1.333(3) . ?
N1 C5 1.330(3) . ?
N1 H1 1.07(4) . ?
N3 O3 1.189(3) . ?
N2 C6 1.329(3) . ?
N2 C7 1.447(3) . ?
N2 H2 0.78(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.374(3) . ?
C2 C6 1.495(4) . ?
C2 C3 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.482(3) . ?
C11 C10 1.301(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.477(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.495(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 H4 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C8 C7 N2 -58.0(3) . . . . ?
N1 C1 C2 C6 178.1(2) . . . . ?
N1 C1 C2 C3 -1.0(3) . . . . ?
N1 C5 C4 C3 -1.2(4) . . . . ?
N3 O2 C8 C7 -76.1(3) . . . . ?
C1 N1 C5 C4 -0.1(4) . . . . ?
C1 C2 C6 O1 -159.3(2) . . . . ?
C1 C2 C6 N2 21.5(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C11 C10 C9 O5 -9.3(4) . . . . ?
C11 C10 C9 O6 171.2(3) . . . . ?
C6 N2 C7 C8 98.6(3) . . . . ?
C6 C2 C3 C4 -179.5(2) . . . . ?
C3 C2 C6 O1 19.8(3) . . . . ?
C3 C2 C6 N2 -159.3(2) . . . . ?
C12 C11 C10 C9 178.4(2) . . . . ?
C10 C11 C12 O8 2.8(4) . . . . ?
C10 C11 C12 O7 -177.1(2) . . . . ?
C8 O2 N3 O4 -0.1(3) . . . . ?
C8 O2 N3 O3 179.4(2) . . . . ?
C5 N1 C1 C2 1.3(4) . . . . ?
C7 N2 C6 O1 -0.3(4) . . . . ?
C7 N2 C6 C2 178.8(2) . . . . ?
