#------------------------------------------------------------------------------
#$Date: 2019-04-09 05:50:28 +0300 (Tue, 09 Apr 2019) $
#$Revision: 214564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/15/2021576.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021576
loop_
_publ_author_name
'Santiago de Oliveira, Yara'
'Saraiva Costa, Wendell'
'Ferreira Borges, Poliana'
'Silmara Alves de Santana, Maria'
'Ayala, Alejandro Pedro'
_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, 0.5C6 H4 O8'
_chemical_formula_moiety         '2(C13 H13 N3 O4), 0.5(C6 H4 O8)'
_chemical_formula_sum            'C29 H28 N6 O12'
_chemical_formula_weight         652.57
_chemical_name_common
;
Benzoylmetronidazole--malonic acid (4/1)
;
_chemical_name_systematic
;
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate--malonic acid (4/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.1542(4)
_cell_length_b                   7.27080(10)
_cell_length_c                   16.6719(3)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    300
_cell_measurement_theta_max      72.47
_cell_measurement_theta_min      3.14
_cell_volume                     3170.36(9)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009),
MERCURY (Version 3.10; Macrae et al.,  2008) and
VEGA (Pedretti et al., 2004)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54755
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         5.570
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.9074
_exptl_absorpt_correction_T_min  0.7355
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.268
_refine_ls_extinction_coef       0.0039(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1596P)²+0.3629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.2678
_reflns_number_gt                2423
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3032sup1.cif
_cod_data_source_block           bzmdmln
_cod_database_code               2021576
_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_min   0.679
_shelx_estimated_absorpt_t_max   0.889
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.29519(7) 0.6661(3) 0.53894(10) 0.1002(6) Uani d 1 . .
O O4 0.21543(9) 0.6847(4) 0.58610(14) 0.1407(10) Uani d 1 . .
N N1 0.39769(8) 0.5613(3) 0.58207(13) 0.0982(6) Uani d 1 . .
C C7 0.24416(10) 0.6583(4) 0.53037(16) 0.0976(7) Uani d 1 . .
N N2 0.44070(10) 0.3861(5) 0.49826(17) 0.1221(9) Uani d 1 . .
C C13 0.26247(11) 0.5592(3) 0.39102(16) 0.0990(7) Uani d 1 . .
H H13 0.297280 0.557512 0.402389 0.119 Uiso calc 1 . .
N N3 0.39562(11) 0.3512(5) 0.7007(2) 0.1341(10) Uani d 1 A 2
C C8 0.22811(9) 0.6113(3) 0.44877(16) 0.0912(7) Uani d 1 . .
O O1 0.36955(13) 0.4498(6) 0.73879(15) 0.1791(15) Uani d 1 A 2
C C6 0.31291(13) 0.6898(5) 0.61932(18) 0.1201(10) Uani d 1 . .
H H6A 0.304906 0.581714 0.651065 0.144 Uiso calc 1 . .
H H6B 0.296435 0.795389 0.643718 0.144 Uiso calc 1 . .
C C5 0.36982(14) 0.7184(5) 0.6162(2) 0.1214(10) Uani d 1 . .
H H5A 0.377022 0.826914 0.584294 0.146 Uiso calc 1 . .
H H5B 0.382282 0.741023 0.670087 0.146 Uiso calc 1 . .
C C1 0.41726(10) 0.5501(5) 0.50779(16) 0.1076(9) Uani d 1 . .
C C2 0.43619(11) 0.2967(5) 0.5682(2) 0.1165(9) Uani d 1 . .
H H2 0.449468 0.180669 0.579041 0.140 Uiso calc 1 . .
C C12 0.24521(15) 0.5095(5) 0.31615(19) 0.1220(10) Uani d 1 . .
H H12 0.268778 0.474998 0.277171 0.146 Uiso calc 1 . .
C C9 0.17676(12) 0.6158(5) 0.4293(2) 0.1239(10) Uani d 1 . .
H H9 0.152766 0.653022 0.467173 0.149 Uiso calc 1 . .
O O2 0.41029(16) 0.2059(6) 0.7247(3) 0.2129(19) Uani d 1 A 2
C C3 0.40976(10) 0.3995(4) 0.61981(18) 0.1060(8) Uani d 1 . .
C C10 0.16136(17) 0.5646(7) 0.3534(3) 0.1490(15) Uani d 1 . .
H H10 0.126798 0.568399 0.340365 0.179 Uiso calc 1 . .
C C11 0.1952(2) 0.5094(6) 0.2979(2) 0.1391(13) Uani d 1 . .
H H11 0.184141 0.471593 0.247515 0.167 Uiso calc 1 . .
C C4 0.41453(17) 0.6957(7) 0.4471(3) 0.1555(16) Uani d 1 . .
H H4A 0.380368 0.743804 0.445026 0.233 Uiso calc 1 . .
H H4B 0.423554 0.646143 0.395651 0.233 Uiso calc 1 . .
H H4C 0.437869 0.792578 0.460914 0.233 Uiso calc 1 . .
O O1' 0.4899(3) 0.1937(13) 0.3802(4) 0.138(3) Uani d 0.5 B 1
H H1' 0.462376 0.171352 0.401729 0.207 Uiso calc 0.5 B 1
C C1' 0.4823(3) 0.2427(12) 0.3078(5) 0.106(2) Uani d 0.5 B 1
O O2' 0.4576(4) 0.3627(13) 0.2891(5) 0.213(4) Uani d 0.5 B 1
C C2' 0.500000 0.1017(7) 0.250000 0.1213(13) Uani d 1 . .
O O2" 0.5116(4) 0.1127(9) 0.3942(4) 0.152(2) Uani d 0.5 B 2
C C1" 0.4925(3) 0.1738(11) 0.3373(6) 0.105(2) Uani d 0.5 B 2
O O1" 0.4611(3) 0.3098(12) 0.3421(5) 0.185(3) Uani d 0.5 B 2
H H1" 0.450297 0.317907 0.388154 0.277 Uiso calc 0.5 B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 O3 C6 . . 115.3(2)
C1 N1 C5 . . 126.4(3)
C1 N1 C3 . . 106.4(2)
C3 N1 C5 . . 127.1(3)
O3 C7 C8 . . 113.2(2)
O4 C7 O3 . . 121.9(3)
O4 C7 C8 . . 124.9(3)
C2 N2 C1 . . 106.6(3)
C8 C13 C12 . . 119.7(3)
O1 N3 O2 . . 122.9(4)
O1 N3 C3 . . 120.4(3)
O2 N3 C3 . . 116.6(4)
C13 C8 C7 . . 122.0(2)
C13 C8 C9 . . 118.6(3)
C9 C8 C7 . . 119.4(3)
O3 C6 C5 . . 107.8(3)
N1 C5 C6 . . 113.4(3)
N1 C1 N2 . . 109.6(3)
N1 C1 C4 . . 125.0(3)
N2 C1 C4 . . 125.4(3)
C3 C2 N2 . . 109.6(3)
C11 C12 C13 . . 121.7(3)
C10 C9 C8 . . 119.5(3)
N1 C3 N3 . . 125.4(3)
C2 C3 N1 . . 107.7(3)
C2 C3 N3 . . 126.9(3)
C11 C10 C9 . . 121.4(4)
C10 C11 C12 . . 119.1(4)
O1' C1' C2' . . 112.0(7)
O2' C1' O1' . . 124.5(8)
O2' C1' C2' . . 122.3(7)
C1' C2' C1' 3_655 . 92.4(7)
C1' C2' C1" 3_655 3_655 28.4(3)
C1' C2' C1" . 3_655 114.4(6)
C1" C2' C1" 3_655 . 140.7(7)
O2" C1" C2' . . 125.5(7)
O2" C1" O1" . . 121.1(10)
O1" C1" C2' . . 113.4(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O3 C7 . 1.344(3)
O3 C6 . 1.428(4)
O4 C7 . 1.210(3)
N1 C5 . 1.469(4)
N1 C1 . 1.343(4)
N1 C3 . 1.371(4)
C7 C8 . 1.464(4)
N2 C1 . 1.350(4)
N2 C2 . 1.340(4)
C13 C8 . 1.370(4)
C13 C12 . 1.376(4)
N3 O1 . 1.176(4)
N3 O2 . 1.193(4)
N3 C3 . 1.441(4)
C8 C9 . 1.382(4)
C6 C5 . 1.504(5)
C1 C4 . 1.466(5)
C2 C3 . 1.333(4)
C12 C11 . 1.344(5)
C9 C10 . 1.380(6)
C10 C11 . 1.341(6)
O1' C1' . 1.274(9)
C1' O2' . 1.129(9)
C1' C2' . 1.482(9)
C2' C1" . 1.559(10)
C2' C1" 3_655 1.559(10)
O2" C1" . 1.161(11)
C1" O1" . 1.288(9)

_cod_database_fobs_code 2021576
