#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506801.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_4506801
loop_
_publ_author_name
'Vangala, Venu R.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Co-Crystals and Co-Crystal Hydrates of the Antibiotic Nitrofurantoin:
 Structural Studies and Physicochemical Properties
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5925
_journal_paper_doi               10.1021/cg300887p
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C8 H6 N4 O5, C H4 N2 O'
_chemical_formula_sum            'C9 H10 N6 O6'
_chemical_formula_weight         298.23
_chemical_name_common            '1:1 cocrystal of nitrofurantoin and urea'
_chemical_name_systematic        '1:1 cocrystal of nitrofurantoin and urea'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6779(13)
_cell_length_b                   13.648(3)
_cell_length_c                   14.003(4)
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.0604
_cell_measurement_theta_min      2.1569
_cell_volume                     1191.9(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 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     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7309
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Rigaku 2007)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0403
_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)+(0.0469P)²+0.6460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                2033
_reflns_number_total             2080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300887p_si_001.cif
_cod_data_source_block           NF-urea(1:1)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 /c'
_cod_database_code               4506801
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.85936(17) -0.22534(8) 0.93747(8) 0.0196(3) Uani 1 1 d .
O2 O 0.9423(2) -0.44386(8) 0.83229(9) 0.0298(3) Uani 1 1 d .
O3 O 0.8192(2) -0.30260(9) 0.76368(9) 0.0284(3) Uani 1 1 d .
O4 O 0.59157(19) 0.10071(8) 0.85121(8) 0.0253(3) Uani 1 1 d .
O5 O 0.6826(2) 0.25096(8) 1.15622(9) 0.0276(3) Uani 1 1 d .
N1 N 0.8915(2) -0.35772(10) 0.83773(10) 0.0221(3) Uani 1 1 d .
N2 N 0.7750(2) -0.04487(9) 0.99154(10) 0.0186(3) Uani 1 1 d .
N3 N 0.7332(2) 0.04657(9) 1.01835(10) 0.0188(3) Uani 1 1 d .
N4 N 0.6134(2) 0.19889(9) 0.99077(10) 0.0199(3) Uani 1 1 d .
H4 H 0.5580 0.2557 0.9549 0.024 Uiso 1 1 d R
C1 C 0.9131(2) -0.20327(11) 1.03939(11) 0.0193(3) Uani 1 1 d .
C2 C 1.0074(3) -0.28195(12) 1.09859(12) 0.0229(4) Uani 1 1 d .
H2B H 1.0597 -0.2850 1.1712 0.027 Uiso 1 1 calc R
C3 C 1.0122(3) -0.35817(12) 1.03077(12) 0.0230(4) Uani 1 1 d .
H3A H 1.0671 -0.4226 1.0481 0.028 Uiso 1 1 calc R
C4 C 0.9222(2) -0.31973(11) 0.93657(12) 0.0203(3) Uani 1 1 d .
C5 C 0.8677(2) -0.10539(11) 1.06448(12) 0.0190(3) Uani 1 1 d .
H5C H 0.9056 -0.0858 1.1338 0.023 Uiso 1 1 calc R
C6 C 0.6400(2) 0.11420(11) 0.94208(12) 0.0188(3) Uani 1 1 d .
C7 C 0.6858(2) 0.18902(11) 1.09505(12) 0.0198(3) Uani 1 1 d .
C8 C 0.7745(3) 0.08575(11) 1.12019(11) 0.0197(3) Uani 1 1 d .
H8A H 0.9297 0.0863 1.1615 0.024 Uiso 1 1 calc R
H8B H 0.6974 0.0483 1.1569 0.024 Uiso 1 1 calc R
O6 O 0.52526(19) -0.11681(8) 0.57328(8) 0.0247(3) Uani 1 1 d .
N5 N 0.6197(3) -0.09166(10) 0.74401(11) 0.0293(3) Uani 1 1 d .
H5A H 0.6329 -0.1550 0.7550 0.035 Uiso 1 1 d R
H5B H 0.6453 -0.0476 0.7984 0.035 Uiso 1 1 d R
N6 N 0.5347(2) 0.03817(10) 0.63208(10) 0.0254(3) Uani 1 1 d .
H6A H 0.5162 0.0615 0.5692 0.030 Uiso 1 1 d R
H6B H 0.5806 0.0755 0.6886 0.030 Uiso 1 1 d R
C9 C 0.5596(2) -0.05906(12) 0.64674(11) 0.0201(3) Uani 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
C4 O1 C1 104.53(12)
O3 N1 O2 124.33(13)
O3 N1 C4 118.26(13)
O2 N1 C4 117.40(13)
C5 N2 N3 117.24(13)
N2 N3 C6 118.70(12)
N2 N3 C8 128.48(12)
C6 N3 C8 112.82(13)
C7 N4 C6 112.57(13)
C7 N4 H4 125.5
C6 N4 H4 121.9
C2 C1 O1 110.52(14)
C2 C1 C5 132.29(15)
O1 C1 C5 117.17(13)
C1 C2 C3 106.65(14)
C1 C2 H2B 126.7
C3 C2 H2B 126.7
C4 C3 C2 105.18(14)
C4 C3 H3A 127.4
C2 C3 H3A 127.4
C3 C4 O1 113.11(13)
C3 C4 N1 132.11(15)
O1 C4 N1 114.69(13)
N2 C5 C1 119.01(14)
N2 C5 H5C 120.5
C1 C5 H5C 120.5
O4 C6 N3 126.10(14)
O4 C6 N4 127.71(14)
N3 C6 N4 106.20(13)
O5 C7 N4 126.65(15)
O5 C7 C8 126.02(14)
N4 C7 C8 107.32(12)
N3 C8 C7 101.08(12)
N3 C8 H8A 111.6
C7 C8 H8A 111.6
N3 C8 H8B 111.6
C7 C8 H8B 111.6
H8A C8 H8B 109.4
C9 N5 H5A 118.4
C9 N5 H5B 120.7
H5A N5 H5B 120.9
C9 N6 H6A 117.7
C9 N6 H6B 116.2
H6A N6 H6B 122.9
O6 C9 N6 121.37(14)
O6 C9 N5 121.54(15)
N6 C9 N5 117.08(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3564(19)
O1 C1 1.3748(19)
O2 N1 1.2334(18)
O3 N1 1.2313(18)
O4 C6 1.210(2)
O5 C7 1.2093(19)
N1 C4 1.422(2)
N2 C5 1.287(2)
N2 N3 1.3605(18)
N3 C6 1.380(2)
N3 C8 1.4542(19)
N4 C7 1.371(2)
N4 C6 1.385(2)
N4 H4 0.9259
C1 C2 1.365(2)
C1 C5 1.441(2)
C2 C3 1.417(2)
C2 H2B 0.9500
C3 C4 1.345(2)
C3 H3A 0.9500
C5 H5C 0.9500
C7 C8 1.521(2)
C8 H8A 0.9900
C8 H8B 0.9900
O6 C9 1.2503(19)
N5 C9 1.350(2)
N5 H5A 0.8764
N5 H5B 0.9369
N6 C9 1.344(2)
N6 H6A 0.9030
N6 H6B 0.8980
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
C5 N2 N3 C6 178.02(13)
C5 N2 N3 C8 -1.8(2)
C4 O1 C1 C2 0.44(17)
C4 O1 C1 C5 179.01(13)
O1 C1 C2 C3 -0.50(18)
C5 C1 C2 C3 -178.78(16)
C1 C2 C3 C4 0.35(18)
C2 C3 C4 O1 -0.09(18)
C2 C3 C4 N1 176.15(16)
C1 O1 C4 C3 -0.21(17)
C1 O1 C4 N1 -177.13(12)
O3 N1 C4 C3 -173.86(16)
O2 N1 C4 C3 5.1(3)
O3 N1 C4 O1 2.3(2)
O2 N1 C4 O1 -178.70(13)
N3 N2 C5 C1 179.46(13)
C2 C1 C5 N2 -179.92(16)
O1 C1 C5 N2 1.9(2)
N2 N3 C6 O4 -0.7(2)
C8 N3 C6 O4 179.16(15)
N2 N3 C6 N4 179.08(12)
C8 N3 C6 N4 -1.07(17)
C7 N4 C6 O4 179.91(15)
C7 N4 C6 N3 0.15(17)
C6 N4 C7 O5 179.97(15)
C6 N4 C7 C8 0.76(17)
N2 N3 C8 C7 -178.73(14)
C6 N3 C8 C7 1.44(16)
O5 C7 C8 N3 179.51(15)
N4 C7 C8 N3 -1.27(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146217
