#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/85/7208574.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_7208574
loop_
_publ_author_name
'Chen, Jia-Mei'
'Wang, Zi-Zhou'
'Wu, Chuan-Bin'
'Li, Song'
'Lu, Tong-Bu'
_publ_section_title
;
 Crystal engineering approach to improve the solubility of mebendazole
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              6221
_journal_paper_doi               10.1039/c2ce25724f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C21 H21 N3 O7'
_chemical_formula_weight         427.41
_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                85.260(5)
_cell_angle_beta                 87.897(5)
_cell_angle_gamma                81.635(5)
_cell_formula_units_Z            2
_cell_length_a                   6.2151(3)
_cell_length_b                   10.7634(8)
_cell_length_c                   15.0123(9)
_cell_measurement_reflns_used    2892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.6602
_cell_measurement_theta_min      2.9522
_cell_volume                     989.86(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Diamond 3.1a'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5058
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6939
_diffrn_reflns_theta_full        65.09
_diffrn_reflns_theta_max         65.09
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  0.9555
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0398
_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)+(0.0571P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2756
_reflns_number_total             3361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25724f.txt
_cod_data_source_block           0711_cjm_110701_4a_2
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208574
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
O3 O -0.6187(2) 0.83785(13) 0.09858(9) 0.0442(3) Uani 1 1 d .
N2 N -0.0792(2) 0.60873(14) 0.26285(9) 0.0330(3) Uani 1 1 d .
O2 O -0.3284(2) 0.75627(15) 0.01593(9) 0.0501(4) Uani 1 1 d .
N1 N -0.0006(2) 0.62141(14) 0.11580(11) 0.0333(3) Uani 1 1 d .
N3 N -0.3428(2) 0.72613(14) 0.16869(10) 0.0342(3) Uani 1 1 d .
O1 O 0.80082(19) 0.39228(13) 0.07449(8) 0.0411(3) Uani 1 1 d .
C12 C 0.1756(3) 0.54607(16) 0.15612(11) 0.0313(4) Uani 1 1 d .
C11 C 0.1249(3) 0.54025(16) 0.24776(11) 0.0311(4) Uani 1 1 d .
C14 C -0.1447(3) 0.65344(15) 0.18124(11) 0.0304(4) Uani 1 1 d .
C2 C 1.0379(3) 0.18457(18) 0.17537(12) 0.0350(4) Uani 1 1 d .
H2 H 1.1296 0.2414 0.1487 0.042 Uiso 1 1 calc R
C8 C 0.5113(3) 0.41425(16) 0.18075(12) 0.0323(4) Uani 1 1 d .
C6 C 0.6832(3) 0.13879(17) 0.22524(11) 0.0329(4) Uani 1 1 d .
H6 H 0.5321 0.1656 0.2343 0.039 Uiso 1 1 calc R
C1 C 0.8152(3) 0.22320(16) 0.18551(11) 0.0307(4) Uani 1 1 d .
C7 C 0.7168(3) 0.34816(17) 0.14300(11) 0.0328(4) Uani 1 1 d .
C3 C 1.1249(3) 0.06261(18) 0.20450(13) 0.0399(4) Uani 1 1 d .
H3A H 1.2773 0.0368 0.1991 0.048 Uiso 1 1 calc R
C4 C 0.9923(3) -0.02172(18) 0.24127(12) 0.0407(4) Uani 1 1 d .
H4 H 1.0532 -0.1057 0.2595 0.049 Uiso 1 1 calc R
C5 C 0.7711(3) 0.01596(18) 0.25157(12) 0.0375(4) Uani 1 1 d .
H5 H 0.6797 -0.0421 0.2766 0.045 Uiso 1 1 calc R
C15 C -0.4216(3) 0.77212(17) 0.08656(12) 0.0350(4) Uani 1 1 d .
C13 C 0.3656(3) 0.48506(16) 0.12074(12) 0.0334(4) Uani 1 1 d .
H13 H 0.3966 0.4908 0.0582 0.040 Uiso 1 1 calc R
C10 C 0.2728(3) 0.47111(17) 0.30778(12) 0.0348(4) Uani 1 1 d .
H10 H 0.2433 0.4673 0.3704 0.042 Uiso 1 1 calc R
C9 C 0.4625(3) 0.40887(17) 0.27301(12) 0.0339(4) Uani 1 1 d .
H9 H 0.5638 0.3606 0.3127 0.041 Uiso 1 1 calc R
C16 C -0.7285(4) 0.8929(2) 0.01851(14) 0.0531(5) Uani 1 1 d .
H16A H -0.6206 0.9061 -0.0293 0.080 Uiso 1 1 calc R
H16B H -0.8141 0.9740 0.0305 0.080 Uiso 1 1 calc R
H16C H -0.8253 0.8362 0.0000 0.080 Uiso 1 1 calc R
H1 H -0.027(3) 0.634(2) 0.0608(16) 0.041(6) Uiso 1 1 d .
H3 H -0.423(3) 0.743(2) 0.2171(16) 0.042(6) Uiso 1 1 d .
O7 O -1.2731(2) 0.94130(14) 0.45515(9) 0.0486(4) Uani 1 1 d .
O6 O -1.3649(2) 0.90231(15) 0.59789(9) 0.0470(4) Uani 1 1 d .
O4 O -0.3276(2) 0.62175(13) 0.41328(9) 0.0402(3) Uani 1 1 d .
O5 O -0.5597(2) 0.75965(13) 0.33162(8) 0.0425(3) Uani 1 1 d .
C17 C -0.5120(3) 0.69810(17) 0.40169(12) 0.0343(4) Uani 1 1 d .
C18 C -0.6600(3) 0.70363(18) 0.48334(12) 0.0373(4) Uani 1 1 d .
H18A H -0.5885 0.7388 0.5314 0.045 Uiso 1 1 calc R
H18B H -0.6843 0.6171 0.5047 0.045 Uiso 1 1 calc R
C20 C -1.0201(3) 0.80498(19) 0.54822(12) 0.0398(4) Uani 1 1 d .
H20A H -1.0525 0.7227 0.5757 0.048 Uiso 1 1 calc R
H20B H -0.9393 0.8430 0.5920 0.048 Uiso 1 1 calc R
C19 C -0.8782(3) 0.78384(18) 0.46471(12) 0.0366(4) Uani 1 1 d .
H19A H -0.9572 0.7424 0.4222 0.044 Uiso 1 1 calc R
H19B H -0.8525 0.8666 0.4357 0.044 Uiso 1 1 calc R
C21 C -1.2298(3) 0.88921(18) 0.52848(12) 0.0363(4) Uani 1 1 d .
H4A H -0.237(4) 0.612(2) 0.3583(19) 0.065(7) Uiso 1 1 d .
H6A H -1.487(5) 0.957(3) 0.579(2) 0.081(9) 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 0.0181 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
C15 O3 C16 116.15(15)
C14 N2 C11 104.00(14)
C14 N1 C12 106.71(15)
C14 N1 H1 124.1(15)
C12 N1 H1 128.2(15)
C14 N3 C15 124.02(16)
C14 N3 H3 116.7(14)
C15 N3 H3 119.2(14)
C13 C12 N1 131.52(16)
C13 C12 C11 123.02(15)
N1 C12 C11 105.46(14)
N2 C11 C12 109.79(14)
N2 C11 C10 130.57(16)
C12 C11 C10 119.64(16)
N2 C14 N1 114.02(15)
N2 C14 N3 121.24(15)
N1 C14 N3 124.73(16)
C3 C2 C1 119.51(16)
C3 C2 H2 120.2
C1 C2 H2 120.2
C13 C8 C9 120.15(16)
C13 C8 C7 117.46(15)
C9 C8 C7 122.38(15)
C5 C6 C1 120.43(16)
C5 C6 H6 119.8
C1 C6 H6 119.8
C2 C1 C6 119.49(15)
C2 C1 C7 119.48(15)
C6 C1 C7 120.53(15)
O1 C7 C8 120.48(15)
O1 C7 C1 119.57(16)
C8 C7 C1 119.84(14)
C4 C3 C2 120.71(17)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 120.09(17)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 119.71(17)
C4 C5 H5 120.1
C6 C5 H5 120.1
O2 C15 O3 126.00(16)
O2 C15 N3 125.64(16)
O3 C15 N3 108.35(15)
C12 C13 C8 117.19(16)
C12 C13 H13 121.4
C8 C13 H13 121.4
C9 C10 C11 117.78(16)
C9 C10 H10 121.1
C11 C10 H10 121.1
C10 C9 C8 122.22(16)
C10 C9 H9 118.9
C8 C9 H9 118.9
O3 C16 H16A 109.5
O3 C16 H16B 109.5
H16A C16 H16B 109.5
O3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C21 O6 H6A 107.5(18)
C17 O4 H4A 113.8(15)
O5 C17 O4 123.53(16)
O5 C17 C18 122.47(15)
O4 C17 C18 114.00(15)
C17 C18 C19 112.17(15)
C17 C18 H18A 109.2
C19 C18 H18A 109.2
C17 C18 H18B 109.2
C19 C18 H18B 109.2
H18A C18 H18B 107.9
C21 C20 C19 112.25(15)
C21 C20 H20A 109.2
C19 C20 H20A 109.2
C21 C20 H20B 109.2
C19 C20 H20B 109.2
H20A C20 H20B 107.9
C18 C19 C20 113.40(15)
C18 C19 H19A 108.9
C20 C19 H19A 108.9
C18 C19 H19B 108.9
C20 C19 H19B 108.9
H19A C19 H19B 107.7
O7 C21 O6 122.41(17)
O7 C21 C20 123.41(16)
O6 C21 C20 114.18(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C15 1.336(2)
O3 C16 1.445(2)
N2 C14 1.334(2)
N2 C11 1.392(2)
O2 C15 1.202(2)
N1 C14 1.337(2)
N1 C12 1.390(2)
N1 H1 0.84(2)
N3 C14 1.369(2)
N3 C15 1.370(2)
N3 H3 0.88(2)
O1 C7 1.228(2)
C12 C13 1.376(2)
C12 C11 1.399(2)
C11 C10 1.401(2)
C2 C3 1.387(3)
C2 C1 1.393(2)
C2 H2 0.9500
C8 C13 1.399(2)
C8 C9 1.405(3)
C8 C7 1.486(2)
C6 C5 1.386(3)
C6 C1 1.395(2)
C6 H6 0.9500
C1 C7 1.496(2)
C3 C4 1.382(3)
C3 H3A 0.9500
C4 C5 1.382(3)
C4 H4 0.9500
C5 H5 0.9500
C13 H13 0.9500
C10 C9 1.376(3)
C10 H10 0.9500
C9 H9 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
O7 C21 1.214(2)
O6 C21 1.318(2)
O6 H6A 0.92(3)
O4 C17 1.317(2)
O4 H4A 0.99(3)
O5 C17 1.218(2)
C17 C18 1.505(3)
C18 C19 1.519(3)
C18 H18A 0.9900
C18 H18B 0.9900
C20 C21 1.499(3)
C20 C19 1.520(3)
C20 H20A 0.9900
C20 H20B 0.9900
C19 H19A 0.9900
C19 H19B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.84(2) 2.22(2) 2.7403(19) 120.1(18) .
N1 H1 O1 0.84(2) 2.44(2) 3.079(2) 133.0(18) 2_665
N3 H3 O5 0.88(2) 1.90(2) 2.774(2) 170(2) .
O4 H4A N2 0.99(3) 1.71(3) 2.6902(19) 175(2) .
O6 H6A O7 0.92(3) 1.79(3) 2.7091(19) 178(3) 2_276
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 138679263
