#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506805.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_4506805
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_sum            'C28 H28 N10 O12'
_chemical_formula_weight         696.60
_chemical_name_common
;
 1:1:1 Cocrystal of nitrofurantoin, 4,4'-bipyridyl ethane and water
;
_chemical_name_systematic
;
 1:0.5:1 Cocrystal of nitrofurantoin, 4,4'-bipyridyl ethane and water
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.54(3)
_cell_angle_beta                 93.68(3)
_cell_angle_gamma                100.76(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4093(13)
_cell_length_b                   13.597(3)
_cell_length_c                   19.138(4)
_cell_measurement_reflns_used    3464
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.1000
_cell_measurement_theta_min      2.2124
_cell_volume                     1558.5(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17186
_diffrn_reflns_theta_full        24.25
_diffrn_reflns_theta_max         24.25
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Rigaku 2007)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0783
_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)+(0.0815P)²+0.8581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.1885
_reflns_number_gt                4193
_reflns_number_total             5002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300887p_si_001.cif
_cod_data_source_block           NF-4,4'-bipyridylethane-H2O(1:0.5:1)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        1558.3(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4506805
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O6 O 0.4626(3) 0.78547(18) 0.17090(13) 0.0295(6) Uani 1 1 d .
O10 O 0.7878(4) 0.59065(19) -0.03915(14) 0.0351(6) Uani 1 1 d .
N9 N 0.5339(4) 0.4971(2) -0.13993(16) 0.0277(7) Uani 1 1 d .
O7 O 0.7727(4) 0.8971(2) 0.27473(14) 0.0368(6) Uani 1 1 d .
O9 O 0.2117(4) 0.4217(2) -0.21363(14) 0.0372(6) Uani 1 1 d .
O8 O 0.5478(4) 0.9626(2) 0.34636(14) 0.0415(7) Uani 1 1 d .
N8 N 0.4242(4) 0.5885(2) -0.03883(15) 0.0283(7) Uani 1 1 d .
N6 N 0.5900(5) 0.9050(2) 0.28853(16) 0.0337(7) Uani 1 1 d .
N7 N 0.4427(4) 0.6531(2) 0.03157(16) 0.0291(7) Uani 1 1 d .
C15 C 0.2689(5) 0.7405(3) 0.12823(19) 0.0287(8) Uani 1 1 d .
C18 C 0.4137(5) 0.8462(3) 0.23502(19) 0.0293(8) Uani 1 1 d .
C21 C 0.3171(5) 0.4781(3) -0.15623(19) 0.0292(8) Uani 1 1 d .
C22 C 0.2286(5) 0.5387(3) -0.08965(19) 0.0294(8) Uani 1 1 d .
H22A H 0.1555 0.5914 -0.1009 0.035 Uiso 1 1 calc R
H22B H 0.1284 0.4913 -0.0702 0.035 Uiso 1 1 calc R
C16 C 0.1080(5) 0.7725(3) 0.16492(19) 0.0291(8) Uani 1 1 d .
H16A H -0.0402 0.7525 0.1470 0.035 Uiso 1 1 calc R
C20 C 0.6041(5) 0.5626(3) -0.06901(19) 0.0286(8) Uani 1 1 d .
C19 C 0.2672(6) 0.6730(3) 0.05545(19) 0.0301(8) Uani 1 1 d .
H19A H 0.1353 0.6426 0.0245 0.036 Uiso 1 1 calc R
C17 C 0.2020(6) 0.8416(3) 0.2354(2) 0.0332(9) Uani 1 1 d .
H17A H 0.1313 0.8767 0.2740 0.040 Uiso 1 1 calc R
O1 O 0.8345(4) 0.10647(18) 0.25548(13) 0.0299(6) Uani 1 1 d .
O4 O 0.2627(4) -0.07318(19) 0.04042(13) 0.0345(6) Uani 1 1 d .
O5 O 0.6324(4) -0.25232(19) -0.13156(13) 0.0355(6) Uani 1 1 d .
N4 N 0.4009(5) -0.1746(2) -0.05800(16) 0.0278(7) Uani 1 1 d .
O2 O 0.6651(4) 0.1988(2) 0.37096(14) 0.0392(6) Uani 1 1 d .
N3 N 0.6187(4) -0.0900(2) 0.04522(15) 0.0286(7) Uani 1 1 d .
O3 O 0.9787(4) 0.2650(2) 0.43623(14) 0.0436(7) Uani 1 1 d .
N2 N 0.6820(5) -0.0225(2) 0.11427(16) 0.0307(7) Uani 1 1 d .
N1 N 0.8610(5) 0.2120(2) 0.37867(16) 0.0317(7) Uani 1 1 d .
C4 C 0.9632(5) 0.1632(3) 0.31885(19) 0.0301(8) Uani 1 1 d .
C8 C 0.7515(5) -0.1424(3) -0.00517(19) 0.0305(8) Uani 1 1 d .
H8A H 0.8115 -0.1934 0.0135 0.037 Uiso 1 1 calc R
H8B H 0.8699 -0.0914 -0.0144 0.037 Uiso 1 1 calc R
C1 C 0.9724(5) 0.0652(3) 0.20902(19) 0.0277(8) Uani 1 1 d .
C7 C 0.5932(5) -0.1970(3) -0.0732(2) 0.0315(8) Uani 1 1 d .
C2 C 1.1770(5) 0.0958(3) 0.2426(2) 0.0315(8) Uani 1 1 d .
H2A H 1.3004 0.0780 0.2216 0.038 Uiso 1 1 calc R
C6 C 0.4094(5) -0.1082(3) 0.0132(2) 0.0290(8) Uani 1 1 d .
C5 C 0.8854(5) -0.0032(3) 0.13696(19) 0.0303(8) Uani 1 1 d .
H5A H 0.9781 -0.0349 0.1052 0.036 Uiso 1 1 calc R
C3 C 1.1714(6) 0.1590(3) 0.3147(2) 0.0348(9) Uani 1 1 d .
H3A H 1.2885 0.1915 0.3524 0.042 Uiso 1 1 calc R
O12 O 0.9477(4) 0.2808(2) 0.15868(15) 0.0395(7) Uani 1 1 d D
O11 O 0.2286(5) 0.5878(2) 0.24364(16) 0.0411(7) Uani 1 1 d .
N10 N 0.8457(5) 0.3946(2) 0.29398(17) 0.0374(8) Uani 1 1 d .
C24 C 0.8616(5) 0.5189(3) 0.4129(2) 0.0340(9) Uani 1 1 d .
H24A H 0.9473 0.5711 0.4538 0.041 Uiso 1 1 calc R
C23 C 0.6421(6) 0.4908(3) 0.41290(19) 0.0329(8) Uani 1 1 d .
C28 C 0.5301(7) 0.5377(3) 0.4770(2) 0.0354(9) Uani 1 1 d .
C27 C 0.5281(6) 0.4139(3) 0.3512(2) 0.0391(9) Uani 1 1 d .
H27A H 0.3770 0.3925 0.3479 0.047 Uiso 1 1 calc R
C26 C 0.6361(6) 0.3684(3) 0.2943(2) 0.0381(9) Uani 1 1 d .
H26A H 0.5548 0.3150 0.2530 0.046 Uiso 1 1 calc R
C25 C 0.9555(6) 0.4705(3) 0.3530(2) 0.0367(9) Uani 1 1 d .
H25A H 1.1056 0.4921 0.3538 0.044 Uiso 1 1 calc R
N5 N 0.4518(5) 0.7134(2) 0.38269(17) 0.0360(7) Uani 1 1 d .
C13 C 0.8229(6) 0.7976(3) 0.4072(2) 0.0335(8) Uani 1 1 d .
H13A H 0.9614 0.8005 0.3918 0.040 Uiso 1 1 calc R
C12 C 0.6513(6) 0.7234(3) 0.3647(2) 0.0343(9) Uani 1 1 d .
H12C H 0.6759 0.6765 0.3202 0.041 Uiso 1 1 calc R
C10 C 0.5876(6) 0.8574(3) 0.4922(2) 0.0350(9) Uani 1 1 d .
H10A H 0.5589 0.9027 0.5368 0.042 Uiso 1 1 calc R
C11 C 0.4252(6) 0.7803(3) 0.4467(2) 0.0370(9) Uani 1 1 d .
H11C H 0.2858 0.7741 0.4614 0.044 Uiso 1 1 calc R
C9 C 0.7940(6) 0.8686(3) 0.4726(2) 0.0340(9) Uani 1 1 d .
C14 C 0.9744(7) 0.9555(3) 0.5174(2) 0.0396(10) Uani 1 1 d .
H9 H 0.635(6) 0.465(3) -0.176(2) 0.057(12) Uiso 1 1 d .
H4 H 0.279(5) -0.196(3) -0.0890(19) 0.025(9) Uiso 1 1 d .
H28B H 0.387(6) 0.557(3) 0.461(2) 0.041(10) Uiso 1 1 d .
H14B H 0.932(6) 0.986(3) 0.570(2) 0.048(11) Uiso 1 1 d .
H11B H 0.083(8) 0.587(3) 0.239(3) 0.068(15) Uiso 1 1 d .
H28A H 0.624(6) 0.600(3) 0.506(2) 0.043(11) Uiso 1 1 d .
H11A H 0.282(9) 0.624(5) 0.289(3) 0.10(2) Uiso 1 1 d .
H12B H 1.092(10) 0.274(5) 0.155(3) 0.11(2) Uiso 1 1 d .
H14A H 1.097(6) 0.936(3) 0.525(2) 0.033(10) Uiso 1 1 d .
H12A H 0.941(8) 0.317(4) 0.2038(14) 0.087(19) Uiso 1 1 d 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
C18 O6 C15 104.7(2) . .
C21 N9 C20 112.3(3) . .
C21 N9 H9 124(2) . .
C20 N9 H9 124(2) . .
N7 N8 C20 120.2(3) . .
N7 N8 C22 127.5(3) . .
C20 N8 C22 112.3(3) . .
O7 N6 O8 124.5(3) . .
O7 N6 C18 119.0(3) . .
O8 N6 C18 116.5(3) . .
C19 N7 N8 116.1(3) . .
C16 C15 O6 110.5(3) . .
C16 C15 C19 131.2(3) . .
O6 C15 C19 118.3(3) . .
C17 C18 O6 113.0(3) . .
C17 C18 N6 131.0(3) . .
O6 C18 N6 116.0(3) . .
O9 C21 N9 126.5(3) . .
O9 C21 C22 125.6(3) . .
N9 C21 C22 107.9(3) . .
N8 C22 C21 101.1(3) . .
N8 C22 H22A 111.6 . .
C21 C22 H22A 111.6 . .
N8 C22 H22B 111.6 . .
C21 C22 H22B 111.6 . .
H22A C22 H22B 109.4 . .
C15 C16 C17 107.3(3) . .
C15 C16 H16A 126.3 . .
C17 C16 H16A 126.3 . .
O10 C20 N8 126.9(3) . .
O10 C20 N9 126.6(3) . .
N8 C20 N9 106.5(3) . .
N7 C19 C15 120.6(3) . .
N7 C19 H19A 119.7 . .
C15 C19 H19A 119.7 . .
C18 C17 C16 104.5(3) . .
C18 C17 H17A 127.7 . .
C16 C17 H17A 127.7 . .
C4 O1 C1 104.1(3) . .
C7 N4 C6 112.5(3) . .
C7 N4 H4 126(2) . .
C6 N4 H4 121(2) . .
N2 N3 C6 120.2(3) . .
N2 N3 C8 127.5(3) . .
C6 N3 C8 112.1(3) . .
C5 N2 N3 115.6(3) . .
O2 N1 O3 124.5(3) . .
O2 N1 C4 118.9(3) . .
O3 N1 C4 116.6(3) . .
C3 C4 O1 112.9(3) . .
C3 C4 N1 130.4(3) . .
O1 C4 N1 116.6(3) . .
N3 C8 C7 101.8(3) . .
N3 C8 H8A 111.4 . .
C7 C8 H8A 111.4 . .
N3 C8 H8B 111.4 . .
C7 C8 H8B 111.4 . .
H8A C8 H8B 109.3 . .
C2 C1 O1 111.0(3) . .
C2 C1 C5 130.4(3) . .
O1 C1 C5 118.5(3) . .
O5 C7 N4 126.4(3) . .
O5 C7 C8 125.9(3) . .
N4 C7 C8 107.7(3) . .
C1 C2 C3 106.8(3) . .
C1 C2 H2A 126.6 . .
C3 C2 H2A 126.6 . .
O4 C6 N3 127.8(3) . .
O4 C6 N4 126.4(3) . .
N3 C6 N4 105.9(3) . .
N2 C5 C1 121.3(3) . .
N2 C5 H5A 119.4 . .
C1 C5 H5A 119.4 . .
C4 C3 C2 105.1(3) . .
C4 C3 H3A 127.4 . .
C2 C3 H3A 127.4 . .
H12B O12 H12A 107(5) . .
H11B O11 H11A 107(5) . .
C26 N10 C25 116.4(3) . .
C25 C24 C23 119.8(3) . .
C25 C24 H24A 120.1 . .
C23 C24 H24A 120.1 . .
C27 C23 C24 116.7(3) . .
C27 C23 C28 120.6(3) . .
C24 C23 C28 122.7(3) . .
C23 C28 C28 112.3(4) . 2_666
C23 C28 H28B 113(2) . .
C28 C28 H28B 106(2) 2_666 .
C23 C28 H28A 107(2) . .
C28 C28 H28A 111(2) 2_666 .
H28B C28 H28A 108(3) . .
C26 C27 C23 119.5(4) . .
C26 C27 H27A 120.2 . .
C23 C27 H27A 120.2 . .
N10 C26 C27 124.1(4) . .
N10 C26 H26A 117.9 . .
C27 C26 H26A 117.9 . .
N10 C25 C24 123.5(3) . .
N10 C25 H25A 118.3 . .
C24 C25 H25A 118.3 . .
C12 N5 C11 116.1(3) . .
C12 C13 C9 120.2(3) . .
C12 C13 H13A 119.9 . .
C9 C13 H13A 119.9 . .
N5 C12 C13 123.6(3) . .
N5 C12 H12C 118.2 . .
C13 C12 H12C 118.2 . .
C11 C10 C9 119.5(3) . .
C11 C10 H10A 120.2 . .
C9 C10 H10A 120.2 . .
N5 C11 C10 124.1(3) . .
N5 C11 H11C 118.0 . .
C10 C11 H11C 118.0 . .
C10 C9 C13 116.5(3) . .
C10 C9 C14 121.9(3) . .
C13 C9 C14 121.5(3) . .
C9 C14 C14 111.9(4) . 2_776
C9 C14 H14B 109(2) . .
C14 C14 H14B 109(2) 2_776 .
C9 C14 H14A 115(2) . .
C14 C14 H14A 107(2) 2_776 .
H14B C14 H14A 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C18 1.362(4) .
O6 C15 1.372(4) .
O10 C20 1.217(4) .
N9 C21 1.364(4) .
N9 C20 1.386(5) .
N9 H9 1.04(4) .
O7 N6 1.234(4) .
O9 C21 1.218(4) .
O8 N6 1.239(4) .
N8 N7 1.366(4) .
N8 C20 1.381(4) .
N8 C22 1.459(4) .
N6 C18 1.419(5) .
N7 C19 1.287(4) .
C15 C16 1.354(5) .
C15 C19 1.431(5) .
C18 C17 1.347(5) .
C21 C22 1.514(5) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C16 C17 1.424(5) .
C16 H16A 0.9500 .
C19 H19A 0.9500 .
C17 H17A 0.9500 .
O1 C4 1.359(4) .
O1 C1 1.374(4) .
O4 C6 1.212(4) .
O5 C7 1.225(4) .
N4 C7 1.354(4) .
N4 C6 1.396(5) .
N4 H4 0.90(3) .
O2 N1 1.228(4) .
N3 N2 1.362(4) .
N3 C6 1.386(4) .
N3 C8 1.450(4) .
O3 N1 1.241(4) .
N2 C5 1.300(4) .
N1 C4 1.416(4) .
C4 C3 1.353(5) .
C8 C7 1.508(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C1 C2 1.357(5) .
C1 C5 1.433(5) .
C2 C3 1.410(5) .
C2 H2A 0.9500 .
C5 H5A 0.9500 .
C3 H3A 0.9500 .
O12 H12B 0.95(6) .
O12 H12A 0.87(2) .
O11 H11B 0.93(5) .
O11 H11A 0.87(6) .
N10 C26 1.325(5) .
N10 C25 1.341(5) .
C24 C25 1.383(5) .
C24 C23 1.388(5) .
C24 H24A 0.9500 .
C23 C27 1.387(5) .
C23 C28 1.505(5) .
C28 C28 1.544(7) 2_666
C28 H28B 1.05(4) .
C28 H28A 0.94(4) .
C27 C26 1.385(5) .
C27 H27A 0.9500 .
C26 H26A 0.9500 .
C25 H25A 0.9500 .
N5 C12 1.338(5) .
N5 C11 1.344(5) .
C13 C12 1.375(5) .
C13 C9 1.393(5) .
C13 H13A 0.9500 .
C12 H12C 0.9500 .
C10 C11 1.378(5) .
C10 C9 1.392(5) .
C10 H10A 0.9500 .
C11 H11C 0.9500 .
C9 C14 1.502(5) .
C14 C14 1.535(7) 2_776
C14 H14B 1.04(4) .
C14 H14A 0.89(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146221
