#------------------------------------------------------------------------------
#$Date: 2017-10-31 05:26:38 +0200 (Tue, 31 Oct 2017) $
#$Revision: 202438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/94/7229422.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_7229422
loop_
_publ_author_name
'Sarma, Bipul'
'Khatioda, Rajiv'
'Saikia, Basanta'
'Das, Pranab Jyoti'
_publ_section_title
;
 Solubility and In-vitro Drug Permeation Behaviour of Ethenzamide
 Cocrystals Regulated at Physiological pH Environments
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01626C
_journal_year                    2017
_chemical_formula_sum            'C16 H16 N O6'
_chemical_formula_weight         318.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-10-04 deposited with the CCDC.
2017-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.55(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.720(5)
_cell_length_b                   4.0408(12)
_cell_length_c                   23.577(7)
_cell_measurement_reflns_used    2445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.10
_cell_measurement_theta_min      2.85
_cell_volume                     1496.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1281
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17630
_diffrn_reflns_theta_full        31.87
_diffrn_reflns_theta_max         31.87
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0859
_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)+(0.1065P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2317
_reflns_number_gt                1761
_reflns_number_total             4810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01626c2.cif
_cod_data_source_block           zmd34dhba
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1496.2(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7229422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C15 C 0.63011(18) -0.0347(8) 0.33638(11) 0.0428(7) Uani 1 1 d .
H15A H 0.5963 -0.1878 0.3577 0.051 Uiso 1 1 calc R
H15B H 0.6362 0.1699 0.3577 0.051 Uiso 1 1 calc R
O6 O 0.58985(11) 0.0271(5) 0.28105(7) 0.0421(5) Uani 1 1 d .
C12 C 0.39394(18) 0.4507(7) 0.31876(13) 0.0436(7) Uani 1 1 d .
H12 H 0.3681 0.5287 0.3509 0.052 Uiso 1 1 calc R
O2 O 0.08744(10) 0.0605(5) -0.03813(7) 0.0398(5) Uani 1 1 d .
O4 O 0.43666(10) 0.7602(5) 0.03260(7) 0.0420(5) Uani 1 1 d .
O3 O 0.38887(12) 0.4378(6) -0.06273(8) 0.0537(7) Uani 1 1 d .
C16 C 0.71505(18) -0.1793(9) 0.32634(12) 0.0546(9) Uani 1 1 d .
H16A H 0.7460 -0.0332 0.3026 0.082 Uiso 1 1 calc R
H16B H 0.7079 -0.3900 0.3079 0.082 Uiso 1 1 calc R
H16C H 0.7461 -0.2081 0.3620 0.082 Uiso 1 1 calc R
N2 N 0.57700(15) -0.0784(7) 0.16965(11) 0.0460(7) Uani 1 1 d .
C13 C 0.35361(17) 0.4946(8) 0.26627(14) 0.0462(8) Uani 1 1 d .
H13 H 0.3018 0.6051 0.2626 0.055 Uiso 1 1 calc R
C11 C 0.47088(18) 0.2955(8) 0.32483(12) 0.0423(7) Uani 1 1 d .
H11 H 0.4966 0.2688 0.3608 0.051 Uiso 1 1 calc R
C14 C 0.39235(17) 0.3694(8) 0.21869(12) 0.0427(7) Uani 1 1 d .
H14 H 0.3649 0.3916 0.1831 0.051 Uiso 1 1 calc R
O5 O 0.46291(12) 0.1319(6) 0.12327(8) 0.0520(6) Uani 1 1 d .
C6 C 0.29877(15) 0.6744(7) 0.07109(10) 0.0344(6) Uani 1 1 d .
H6 H 0.3136 0.7917 0.1040 0.041 Uiso 1 1 calc R
C5 C 0.35672(15) 0.6374(7) 0.02941(10) 0.0320(6) Uani 1 1 d .
C10 C 0.51123(15) 0.1765(8) 0.27736(11) 0.0364(7) Uani 1 1 d .
C9 C 0.47069(15) 0.2130(7) 0.22311(11) 0.0340(6) Uani 1 1 d .
C8 C 0.50427(16) 0.0828(7) 0.16848(11) 0.0357(7) Uani 1 1 d .
C1 C 0.10917(15) 0.2140(7) 0.00642(10) 0.0320(6) Uani 1 1 d .
C2 C 0.19459(14) 0.3637(7) 0.01433(10) 0.0296(6) Uani 1 1 d .
C7 C 0.21798(16) 0.5357(7) 0.06375(10) 0.0328(6) Uani 1 1 d .
H7 H 0.1792 0.5581 0.0922 0.039 Uiso 1 1 calc R
C3 C 0.25293(14) 0.3305(7) -0.02797(10) 0.0320(6) Uani 1 1 d .
H3 H 0.2377 0.2176 -0.0613 0.038 Uiso 1 1 calc R
C4 C 0.33330(15) 0.4651(7) -0.02056(10) 0.0333(6) Uani 1 1 d .
O1 O 0.05882(12) 0.2470(6) 0.04822(8) 0.0441(6) Uani 1 1 d .
H1A H 0.0159(19) 0.142(8) 0.0441(12) 0.049(10) Uiso 1 1 d .
H2B H 0.5992(16) -0.182(7) 0.1397(12) 0.044(8) Uiso 1 1 d .
H2A H 0.607(2) -0.132(9) 0.2031(14) 0.067(10) Uiso 1 1 d .
H3A H 0.461(4) 0.437(16) -0.060(3) 0.20(2) 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
O6 C15 C16 106.5(2)
O6 C15 H15A 110.4
C16 C15 H15A 110.4
O6 C15 H15B 110.4
C16 C15 H15B 110.4
H15A C15 H15B 108.6
C10 O6 C15 119.3(2)
C11 C12 C13 121.6(3)
C11 C12 H12 119.2
C13 C12 H12 119.2
C4 O3 H3A 129(3)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 N2 H2B 125.3(17)
C8 N2 H2A 123(2)
H2B N2 H2A 111(3)
C12 C13 C14 118.4(3)
C12 C13 H13 120.8
C14 C13 H13 120.8
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
C9 C14 C13 121.6(3)
C9 C14 H14 119.2
C13 C14 H14 119.2
C5 C6 C7 119.7(2)
C5 C6 H6 120.1
C7 C6 H6 120.1
O4 C5 C6 124.3(2)
O4 C5 C4 116.0(2)
C6 C5 C4 119.7(2)
O6 C10 C11 122.7(2)
O6 C10 C9 118.1(2)
C11 C10 C9 119.2(2)
C14 C9 C10 118.7(2)
C14 C9 C8 116.0(2)
C10 C9 C8 125.2(2)
O5 C8 N2 121.3(3)
O5 C8 C9 119.2(2)
N2 C8 C9 119.5(2)
O2 C1 O1 122.3(2)
O2 C1 C2 121.4(2)
O1 C1 C2 116.3(2)
C3 C2 C7 119.4(2)
C3 C2 C1 119.6(2)
C7 C2 C1 121.0(2)
C6 C7 C2 120.7(2)
C6 C7 H7 119.6
C2 C7 H7 119.6
C4 C3 C2 120.0(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
O3 C4 C3 119.4(2)
O3 C4 C5 120.1(2)
C3 C4 C5 120.4(2)
C1 O1 H1A 113(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C15 O6 1.446(3)
C15 C16 1.486(4)
C15 H15A 0.9700
C15 H15B 0.9700
O6 C10 1.375(3)
C12 C11 1.364(4)
C12 C13 1.377(4)
C12 H12 0.9300
O2 C1 1.254(3)
O4 C5 1.350(3)
O3 C4 1.357(3)
O3 H3A 1.13(6)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
N2 C8 1.315(3)
N2 H2B 0.90(3)
N2 H2A 0.93(3)
C13 C14 1.395(4)
C13 H13 0.9300
C11 C10 1.396(4)
C11 H11 0.9300
C14 C9 1.384(4)
C14 H14 0.9300
O5 C8 1.240(3)
C6 C5 1.378(3)
C6 C7 1.392(3)
C6 H6 0.9300
C5 C4 1.403(3)
C10 C9 1.411(3)
C9 C8 1.508(4)
C1 O1 1.298(3)
C1 C2 1.477(3)
C2 C3 1.391(3)
C2 C7 1.392(3)
C7 H7 0.9300
C3 C4 1.379(3)
C3 H3 0.9300
O1 H1A 0.80(3)
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
C16 C15 O6 C10 -177.0(2)
C11 C12 C13 C14 1.4(5)
C13 C12 C11 C10 0.1(5)
C12 C13 C14 C9 -2.0(4)
C7 C6 C5 O4 -179.5(2)
C7 C6 C5 C4 1.1(4)
C15 O6 C10 C11 5.1(4)
C15 O6 C10 C9 -175.6(2)
C12 C11 C10 O6 178.1(3)
C12 C11 C10 C9 -1.2(4)
C13 C14 C9 C10 0.9(4)
C13 C14 C9 C8 178.7(3)
O6 C10 C9 C14 -178.6(2)
C11 C10 C9 C14 0.7(4)
O6 C10 C9 C8 3.8(4)
C11 C10 C9 C8 -176.9(3)
C14 C9 C8 O5 2.7(4)
C10 C9 C8 O5 -179.7(3)
C14 C9 C8 N2 -177.7(3)
C10 C9 C8 N2 -0.1(4)
O2 C1 C2 C3 -1.0(4)
O1 C1 C2 C3 178.2(2)
O2 C1 C2 C7 179.5(2)
O1 C1 C2 C7 -1.3(4)
C5 C6 C7 C2 -1.0(4)
C3 C2 C7 C6 0.1(4)
C1 C2 C7 C6 179.6(2)
C7 C2 C3 C4 0.5(4)
C1 C2 C3 C4 -179.0(2)
C2 C3 C4 O3 -178.4(2)
C2 C3 C4 C5 -0.3(4)
O4 C5 C4 O3 -1.8(4)
C6 C5 C4 O3 177.6(2)
O4 C5 C4 C3 -179.9(2)
C6 C5 C4 C3 -0.5(4)
