#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:27:41 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246711.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_7246711
loop_
_publ_author_name
'Acebedo-Martínez, Francisco Javier'
'Domínguez-Martín, Alicia'
'Alarcón-Payer, Carolina'
'Frontera, Antonio'
'Ibáñez, Ángel'
'Choquesillo-Lazarte, Duane'
_publ_section_title
;
 Evaluation of synthon influence on ethenzamide--polyphenol pharmaceutical
 cocrystals
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3150
_journal_page_last               3163
_journal_paper_doi               10.1039/D3CE00234A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C9 H11 N O2, C3 H3 O'
_chemical_formula_sum            'C12 H14 N O3'
_chemical_formula_weight         220.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-03-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-11 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                99.864(3)
_cell_angle_beta                 99.082(3)
_cell_angle_gamma                107.888(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2548(5)
_cell_length_b                   9.0844(6)
_cell_length_c                   9.5457(5)
_cell_measurement_reflns_used    3416
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.35
_cell_measurement_theta_min      6.57
_cell_volume                     574.80(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex 4, 2022'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9342
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.467
_diffrn_reflns_theta_max         66.467
_diffrn_reflns_theta_min         5.262
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.6877.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.070(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0726P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1790
_reflns_number_total             1958
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00234a2.cif
_cod_data_source_block           ehq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7246710--7246713.cif.
;
_cod_database_code               7246711
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.928
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15112(18) 0.79946(12) 0.17966(11) 0.0781(4) Uani 1 1 d . . . . .
N1 N 0.19059(18) 0.80486(13) -0.04633(12) 0.0635(4) Uani 1 1 d . . . . .
H1A H 0.163357 0.703559 -0.069468 0.076 Uiso 1 1 calc R U . . .
H1B H 0.218181 0.860210 -0.109716 0.076 Uiso 1 1 calc R U . . .
C1 C 0.23964(17) 1.05258(15) 0.12506(13) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.30166(15) 1.08970(11) -0.10497(10) 0.0629(3) Uani 1 1 d . . . . .
C2 C 0.29384(18) 1.15533(15) 0.03285(14) 0.0523(4) Uani 1 1 d . . . . .
C3 C 0.3345(2) 1.31767(17) 0.08268(17) 0.0661(4) Uani 1 1 d . . . . .
H3 H 0.370933 1.385942 0.021696 0.079 Uiso 1 1 calc R U . . .
C4 C 0.3211(2) 1.37783(17) 0.22197(18) 0.0710(4) Uani 1 1 d . . . . .
H4 H 0.349040 1.486589 0.254135 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2672(2) 1.27952(18) 0.31369(16) 0.0681(4) Uani 1 1 d . . . . .
H5 H 0.257619 1.320599 0.407376 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2273(2) 1.11853(17) 0.26463(14) 0.0599(4) Uani 1 1 d . . . . .
H6 H 0.190858 1.051809 0.326884 0.072 Uiso 1 1 calc R U . . .
C7 C 0.19002(18) 0.87525(15) 0.08619(14) 0.0536(3) Uani 1 1 d . . . . .
C8 C 0.3534(2) 1.18944(19) -0.20390(16) 0.0688(4) Uani 1 1 d . . . . .
H8A H 0.487228 1.265341 -0.166528 0.083 Uiso 1 1 calc R U . . .
H8B H 0.262433 1.247694 -0.216571 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3399(3) 1.0831(2) -0.34593(17) 0.0874(5) Uani 1 1 d . . . . .
H9A H 0.378804 1.146308 -0.414236 0.131 Uiso 1 1 calc R U . . .
H9B H 0.205635 1.011454 -0.383621 0.131 Uiso 1 1 calc R U . . .
H9C H 0.426685 1.023123 -0.331168 0.131 Uiso 1 1 calc R U . . .
O3 O -0.09200(15) 0.52848(11) 0.21541(10) 0.0651(3) Uani 1 1 d . . . . .
H3A H -0.015210 0.610811 0.204055 0.098 Uiso 1 1 calc R U . . .
C10 C -0.04387(19) 0.51832(14) 0.35810(13) 0.0522(4) Uani 1 1 d . . . . .
C11 C -0.16779(19) 0.39349(15) 0.40123(14) 0.0557(4) Uani 1 1 d . . . . .
H11 H -0.281111 0.321687 0.335186 0.067 Uiso 1 1 calc R U . . .
C12 C -0.12392(19) 0.37497(14) 0.54219(14) 0.0559(4) Uani 1 1 d . . . . .
H12 H -0.207546 0.290390 0.570172 0.067 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C7 125.76(11) . . ?
C6 C1 C2 117.88(12) . . ?
C6 C1 C7 116.35(11) . . ?
C2 O2 C8 119.76(11) . . ?
O2 C2 C1 117.68(11) . . ?
O2 C2 C3 122.53(12) . . ?
C3 C2 C1 119.78(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.89(13) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.86(13) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.24(13) . . ?
C5 C6 H6 118.9 . . ?
O1 C7 N1 121.66(12) . . ?
O1 C7 C1 119.07(12) . . ?
N1 C7 C1 119.26(11) . . ?
O2 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
O2 C8 C9 107.03(13) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 O3 H3A 109.5 . . ?
O3 C10 C11 117.81(12) . . ?
O3 C10 C12 122.90(11) . 2_566 ?
C11 C10 C12 119.27(12) . 2_566 ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.32(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C12 H12 119.8 2_566 . ?
C11 C12 C10 120.41(12) . 2_566 ?
C11 C12 H12 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2330(16) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.3173(16) . ?
C1 C2 1.4021(17) . ?
C1 C6 1.3926(18) . ?
C1 C7 1.5030(18) . ?
O2 C2 1.3656(15) . ?
O2 C8 1.4317(15) . ?
C2 C3 1.3915(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.494(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O3 H3A 0.8200 . ?
O3 C10 1.3778(15) . ?
C10 C11 1.3835(18) . ?
C10 C12 1.3859(19) 2_566 ?
C11 H11 0.9300 . ?
C11 C12 1.3840(18) . ?
C12 H12 0.9300 . ?
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
_geom_hbond_publ_flag
N1 H1A O3 0.86 2.18 2.9861(15) 156.2 2_565 yes
N1 H1B O2 0.86 1.97 2.6488(14) 134.4 . yes
O3 H3A O1 0.82 1.84 2.6642(13) 178.0 . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.2(2) . . . . ?
O2 C2 C3 C4 178.82(12) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C7 O1 177.56(12) . . . . ?
C2 C1 C7 N1 -1.95(19) . . . . ?
C2 O2 C8 C9 -177.43(12) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C6 C1 C2 O2 -178.63(10) . . . . ?
C6 C1 C2 C3 0.47(19) . . . . ?
C6 C1 C7 O1 -3.41(18) . . . . ?
C6 C1 C7 N1 177.08(11) . . . . ?
C7 C1 C2 O2 0.39(19) . . . . ?
C7 C1 C2 C3 179.48(12) . . . . ?
C7 C1 C6 C5 -179.42(12) . . . . ?
C8 O2 C2 C1 179.07(11) . . . . ?
C8 O2 C2 C3 0.0(2) . . . . ?
O3 C10 C11 C12 178.30(11) . . . . ?
C10 C11 C12 C10 0.4(2) . . . 2_566 ?
C12 C10 C11 C12 -0.4(2) 2_566 . . . ?
