The design of novel metronidazole benzoate structures: exploring stoichiometric diversity
Santiago de Oliveira, Yara; Saraiva Costa, Wendell; Ferreira Borges, Poliana; Silmara Alves de Santana, Maria; Ayala, Alejandro Pedro; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619003838

data_2021575
_publ_section_title
;
 The design of novel metronidazole benzoate structures: exploring
 stoichiometric diversity
;
_journal_coeditor_code           JX3032
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619003838
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '2C13 H13 N3 O4, C4 H4 O4'
_chemical_formula_moiety         '2(C13 H13 N3 O4), C4 H4 O4'
_chemical_formula_sum            'C30 H30 N6 O12'
_chemical_formula_weight         666.60
_chemical_name_common
;
Benzoylmetronidazole--fumaric acid (2/1)
;
_chemical_name_systematic
;
2-(2-Methyl-5-nitro-1<i>H</i>-imidazol-1-yl)ethyl benzoate--fumaric acid (2/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.419(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0358(5)
_cell_length_b                   26.6419(14)
_cell_length_c                   6.8796(3)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      2.31
_cell_volume                     1617.38(14)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009),
<i>MERCURY</i> (Version 3.10; Macrae <i>et al.</i>,  2008) and
<i>VEGA</i> (Pedretti <i>et al.</i>, 2004)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            46849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.769
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.632
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.334
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0514
_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/[\s^2^(Fo^2^)+(0.0568P)^2^+0.5999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2625
_reflns_number_total             3705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jx3032sup1.cif
_cod_data_source_block           bzmdfma
_cod_depositor_comments
;

2019-10-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C13 H13 N3 O4, 0.5(C4 H4 O4)'
_cod_original_formula_iupac      'C13 H13 N3 O4, 0.5C4 H4 O4'
_cod_original_formula_sum        'C15 H15 N3 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     333.30
_cod_database_code               2021575
_cod_database_fobs_code          2021575
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.982
_shelx_hkl_checksum              24512
_shelx_res_checksum              24535