#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/91/7209111.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_7209111
loop_
_publ_author_name
'Vangala, Venu R.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 The solvates and salt of antibiotic agent, nitrofurantoin: structural,
 thermochemical and desolvation studies
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              878
_journal_paper_doi               10.1039/c2ce26575c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H6 N4 O5, C6 H7 N'
_chemical_formula_sum            'C14 H13 N5 O5'
_chemical_formula_weight         331.29
_chemical_name_common            '1:1 nitrofurantoin and 4-picoline'
_chemical_name_systematic        '1:1 nitrofurantoin and 4-picoline'
_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                 91.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.840(3)
_cell_length_b                   8.0152(16)
_cell_length_c                   12.951(3)
_cell_measurement_reflns_used    2770
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.8362
_cell_measurement_theta_min      2.5412
_cell_volume                     1540.2(6)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku Saturn CCD area deterctor'
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8809
_diffrn_reflns_theta_full        24.50
_diffrn_reflns_theta_max         24.50
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0847
_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)+(0.0853P)²+1.1119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2019
_reflns_number_gt                2060
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26575c.txt
_cod_data_source_block           NF-4-Picoline(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_cell_volume        1540.2(5)
_cod_original_sg_symbol_H-M      'P 2 1/c'
_cod_database_code               7209111
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 0.23007(17) 0.5478(3) 0.50044(18) 0.0351(7) Uani 1 1 d .
O4 O 0.00636(18) 0.1985(3) 0.6757(2) 0.0410(7) Uani 1 1 d .
N3 N 0.0032(2) 0.2556(4) 0.5003(2) 0.0324(8) Uani 1 1 d .
O5 O -0.1948(2) 0.0590(3) 0.4185(2) 0.0432(7) Uani 1 1 d .
N2 N 0.0801(2) 0.3503(4) 0.5014(2) 0.0337(8) Uani 1 1 d .
O3 O 0.3400(2) 0.6691(4) 0.6435(2) 0.0506(8) Uani 1 1 d .
N4 N -0.1060(2) 0.1019(4) 0.5641(2) 0.0345(8) Uani 1 1 d .
C8 C -0.0561(3) 0.2208(5) 0.4124(3) 0.0332(9) Uani 1 1 d .
H8A H -0.0246 0.1572 0.3585 0.040 Uiso 1 1 calc R
H8B H -0.0810 0.3248 0.3820 0.040 Uiso 1 1 calc R
C6 C -0.0278(3) 0.1871(4) 0.5907(3) 0.0311(9) Uani 1 1 d .
C1 C 0.1870(2) 0.5074(4) 0.4088(3) 0.0318(9) Uani 1 1 d .
C7 C -0.1283(3) 0.1179(5) 0.4616(3) 0.0339(9) Uani 1 1 d .
C5 C 0.1062(3) 0.4052(4) 0.4134(3) 0.0334(9) Uani 1 1 d .
H5A H 0.0730 0.3791 0.3521 0.040 Uiso 1 1 calc R
C4 C 0.3012(3) 0.6424(5) 0.4717(3) 0.0355(9) Uani 1 1 d .
N1 N 0.3572(2) 0.7040(4) 0.5536(3) 0.0441(9) Uani 1 1 d .
O2 O 0.4207(2) 0.7944(4) 0.5269(2) 0.0547(9) Uani 1 1 d .
C2 C 0.2288(3) 0.5761(4) 0.3276(3) 0.0334(9) Uani 1 1 d .
H2B H 0.2114 0.5665 0.2568 0.040 Uiso 1 1 calc R
C3 C 0.3043(3) 0.6660(5) 0.3689(3) 0.0373(10) Uani 1 1 d .
H3A H 0.3473 0.7288 0.3320 0.045 Uiso 1 1 calc R
N5 N 0.2242(2) 0.4215(4) 0.8223(2) 0.0363(8) Uani 1 1 d .
C12 C 0.2881(3) 0.2689(5) 0.6828(3) 0.0388(10) Uani 1 1 d .
H12A H 0.2813 0.2259 0.6148 0.047 Uiso 1 1 calc R
C10 C 0.3733(3) 0.3102(5) 0.8373(3) 0.0431(10) Uani 1 1 d .
H10A H 0.4265 0.2959 0.8784 0.052 Uiso 1 1 calc R
C13 C 0.2189(3) 0.3568(5) 0.7263(3) 0.0376(10) Uani 1 1 d .
H13A H 0.1649 0.3726 0.6869 0.045 Uiso 1 1 calc R
C9 C 0.3010(3) 0.3975(5) 0.8755(3) 0.0393(10) Uani 1 1 d .
H9A H 0.3062 0.4428 0.9432 0.047 Uiso 1 1 calc R
C11 C 0.3676(3) 0.2432(5) 0.7381(3) 0.0419(10) Uani 1 1 d .
C14 C 0.4446(3) 0.1447(7) 0.6943(4) 0.0673(15) Uani 1 1 d .
H14A H 0.4284 0.1074 0.6243 0.101 Uiso 1 1 calc R
H14B H 0.4569 0.0474 0.7382 0.101 Uiso 1 1 calc R
H14C H 0.4984 0.2152 0.6920 0.101 Uiso 1 1 calc R
H4 H -0.146(3) 0.036(6) 0.607(4) 0.068(15) 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
C4 O1 C1 104.2(3)
N2 N3 C6 120.2(3)
N2 N3 C8 127.3(3)
C6 N3 C8 112.4(3)
C5 N2 N3 116.4(3)
C7 N4 C6 112.4(3)
C7 N4 H4 117(3)
C6 N4 H4 130(3)
N3 C8 C7 101.5(3)
N3 C8 H8A 111.5
C7 C8 H8A 111.5
N3 C8 H8B 111.5
C7 C8 H8B 111.5
H8A C8 H8B 109.3
O4 C6 N3 127.0(4)
O4 C6 N4 126.9(3)
N3 C6 N4 106.1(3)
C2 C1 O1 111.3(3)
C2 C1 C5 130.9(4)
O1 C1 C5 117.8(3)
O5 C7 N4 125.9(4)
O5 C7 C8 126.6(3)
N4 C7 C8 107.6(3)
N2 C5 C1 119.4(3)
N2 C5 H5A 120.3
C1 C5 H5A 120.3
C3 C4 O1 113.1(3)
C3 C4 N1 131.1(4)
O1 C4 N1 115.8(3)
O3 N1 O2 124.6(4)
O3 N1 C4 119.9(3)
O2 N1 C4 115.5(3)
C1 C2 C3 106.4(3)
C1 C2 H2B 126.8
C3 C2 H2B 126.8
C4 C3 C2 105.0(3)
C4 C3 H3A 127.5
C2 C3 H3A 127.5
C9 N5 C13 117.1(3)
C13 C12 C11 120.0(4)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C9 C10 C11 119.5(4)
C9 C10 H10A 120.3
C11 C10 H10A 120.3
N5 C13 C12 123.0(4)
N5 C13 H13A 118.5
C12 C13 H13A 118.5
N5 C9 C10 123.4(4)
N5 C9 H9A 118.3
C10 C9 H9A 118.3
C12 C11 C10 117.1(4)
C12 C11 C14 121.9(4)
C10 C11 C14 121.0(4)
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.358(4)
O1 C1 1.376(4)
O4 C6 1.207(4)
N3 N2 1.371(4)
N3 C6 1.380(5)
N3 C8 1.451(4)
O5 C7 1.220(5)
N2 C5 1.289(5)
O3 N1 1.229(4)
N4 C7 1.367(5)
N4 C6 1.384(5)
N4 H4 0.98(5)
C8 C7 1.504(5)
C8 H8A 0.9900
C8 H8B 0.9900
C1 C2 1.349(5)
C1 C5 1.454(5)
C5 H5A 0.9500
C4 C3 1.346(5)
C4 N1 1.423(5)
N1 O2 1.244(4)
C2 C3 1.428(5)
C2 H2B 0.9500
C3 H3A 0.9500
N5 C9 1.335(5)
N5 C13 1.348(5)
C12 C13 1.375(6)
C12 C11 1.384(6)
C12 H12A 0.9500
C10 C9 1.380(6)
C10 C11 1.394(6)
C10 H10A 0.9500
C13 H13A 0.9500
C9 H9A 0.9500
C11 C14 1.508(6)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196724
