#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/06/7240632.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_7240632
loop_
_publ_author_name
'Bryndal, Iwona'
'Drozd, Marek'
'Lis, Tadeusz'
'Zaręba, Jan Kazimierz'
'Ratajczak, Henryk'
_publ_section_title
;
 Structural diversity of hydrogen-bonded complexes comprising phenol-based
 and pyridine-based components: NLO properties, crystallographic and
 spectroscopic studies
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00606H
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 Cl4 O, C7 H9 N'
_chemical_formula_sum            'C13 H11 Cl4 N O'
_chemical_formula_weight         339.03
_chemical_name_common
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_chemical_name_systematic
'3,5-dimethylpyridine 2,3,5,6-tetrachlorophenol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.02(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.428(3)
_cell_length_b                   6.0198(12)
_cell_length_c                   14.604(3)
_cell_measurement_reflns_used    5060
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.560
_cell_measurement_theta_min      2.827
_cell_volume                     1422.2(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5393
_diffrn_reflns_point_group_measured_fraction_full 0.674
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_min         2.833
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0307P)²+0.3648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0483
_reflns_Friedel_coverage         0.275
_reflns_Friedel_fraction_full    0.348
_reflns_Friedel_fraction_max     0.251
_reflns_number_gt                2569
_reflns_number_total             2572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00606h2.cif
_cod_data_source_block           35l4chfa
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7240632
_shelx_shelxl_version_number     2018/1
_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_min   0.704
_shelx_estimated_absorpt_t_max   0.791
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_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
O1B O 0.20118(8) 0.6907(2) 0.23116(8) 0.0170(2) Uani 1 1 d . . . . .
H1B H 0.242061 0.740709 0.210306 0.026 Uiso 1 1 calc R U . . .
C1B C 0.22294(11) 0.5052(3) 0.27939(11) 0.0127(3) Uani 1 1 d . . . . .
C2B C 0.30483(10) 0.4416(3) 0.31307(11) 0.0128(3) Uani 1 1 d . . . . .
C3B C 0.32167(11) 0.2432(3) 0.36250(11) 0.0133(3) Uani 1 1 d . . . . .
C4B C 0.25842(11) 0.1074(3) 0.38127(12) 0.0143(3) Uani 1 1 d . . . . .
H4B H 0.270468 -0.026859 0.415098 0.017 Uiso 1 1 calc R U . . .
C5B C 0.17698(11) 0.1713(3) 0.34969(11) 0.0138(3) Uani 1 1 d . . . . .
C6B C 0.15937(10) 0.3670(3) 0.29920(11) 0.0129(3) Uani 1 1 d . . . . .
Cl2B Cl 0.38368(2) 0.61333(7) 0.29245(3) 0.01759(9) Uani 1 1 d . . . . .
Cl3B Cl 0.42257(2) 0.16365(7) 0.40254(3) 0.01887(9) Uani 1 1 d . . . . .
Cl5B Cl 0.09776(3) 0.00544(8) 0.37330(3) 0.01986(9) Uani 1 1 d . . . . .
Cl6B Cl 0.05834(2) 0.44533(8) 0.25921(3) 0.01822(9) Uani 1 1 d . . . . .
N1A N 0.27347(10) 0.9875(3) 0.14007(10) 0.0173(3) Uani 1 1 d . . . . .
C2A C 0.34772(12) 1.0659(3) 0.12862(12) 0.0174(3) Uani 1 1 d . . . . .
H2A H 0.395186 0.977930 0.150245 0.021 Uiso 1 1 calc R U . . .
C3A C 0.35881(11) 1.2691(3) 0.08677(12) 0.0177(3) Uani 1 1 d . . . . .
C4A C 0.28775(12) 1.3936(3) 0.05505(11) 0.0177(3) Uani 1 1 d . . . . .
H4A H 0.292579 1.533598 0.026407 0.021 Uiso 1 1 calc R U . . .
C5A C 0.20988(12) 1.3155(3) 0.06481(11) 0.0165(3) Uani 1 1 d . . . . .
C6A C 0.20672(11) 1.1105(3) 0.10829(12) 0.0167(3) Uani 1 1 d . . . . .
H6A H 0.154159 1.054949 0.115818 0.020 Uiso 1 1 calc R U . . .
C7A C 0.44363(13) 1.3491(4) 0.07663(15) 0.0251(4) Uani 1 1 d . . . . .
H71A H 0.485347 1.271438 0.121423 0.038 Uiso 1 1 calc R U . . .
H72A H 0.447705 1.509330 0.088485 0.038 Uiso 1 1 calc R U . . .
H73A H 0.453035 1.318705 0.013377 0.038 Uiso 1 1 calc R U . . .
C8A C 0.13220(13) 1.4462(4) 0.03080(13) 0.0223(4) Uani 1 1 d . . . . .
H81A H 0.118126 1.434679 -0.037046 0.033 Uiso 1 1 calc R U . . .
H82A H 0.141231 1.602456 0.048534 0.033 Uiso 1 1 calc R U . . .
H83A H 0.086760 1.386442 0.058823 0.033 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C1B O1B H1B 109.5 . . ?
O1B C1B C2B 124.44(16) . . ?
O1B C1B C6B 117.62(16) . . ?
C2B C1B C6B 117.92(15) . . ?
C3B C2B C1B 120.38(16) . . ?
C3B C2B Cl2B 121.01(13) . . ?
C1B C2B Cl2B 118.61(13) . . ?
C4B C3B C2B 121.20(16) . . ?
C4B C3B Cl3B 118.54(13) . . ?
C2B C3B Cl3B 120.26(14) . . ?
C3B C4B C5B 118.82(16) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B C6B 120.55(15) . . ?
C4B C5B Cl5B 119.34(13) . . ?
C6B C5B Cl5B 120.11(13) . . ?
C5B C6B C1B 121.11(15) . . ?
C5B C6B Cl6B 120.59(13) . . ?
C1B C6B Cl6B 118.30(13) . . ?
C6A N1A C2A 117.96(16) . . ?
N1A C2A C3A 123.58(17) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 116.82(17) . . ?
C2A C3A C7A 121.18(17) . . ?
C4A C3A C7A 122.00(17) . . ?
C5A C4A C3A 120.93(16) . . ?
C5A C4A H4A 119.5 . . ?
C3A C4A H4A 119.5 . . ?
C6A C5A C4A 116.97(16) . . ?
C6A C5A C8A 121.06(18) . . ?
C4A C5A C8A 121.97(17) . . ?
N1A C6A C5A 123.74(17) . . ?
N1A C6A H6A 118.1 . . ?
C5A C6A H6A 118.1 . . ?
C3A C7A H71A 109.5 . . ?
C3A C7A H72A 109.5 . . ?
H71A C7A H72A 109.5 . . ?
C3A C7A H73A 109.5 . . ?
H71A C7A H73A 109.5 . . ?
H72A C7A H73A 109.5 . . ?
C5A C8A H81A 109.5 . . ?
C5A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
C5A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
H82A C8A H83A 109.5 . . ?
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
O1B C1B 1.335(2) . ?
O1B H1B 0.8400 . ?
C1B C2B 1.403(2) . ?
C1B C6B 1.404(2) . ?
C2B C3B 1.398(2) . ?
C2B Cl2B 1.7243(17) . ?
C3B C4B 1.387(2) . ?
C3B Cl3B 1.7268(18) . ?
C4B C5B 1.391(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.393(2) . ?
C5B Cl5B 1.7221(17) . ?
C6B Cl6B 1.7265(17) . ?
N1A C6A 1.338(2) . ?
N1A C2A 1.345(2) . ?
C2A C3A 1.394(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.397(3) . ?
C3A C7A 1.506(3) . ?
C4A C5A 1.394(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.393(2) . ?
C5A C8A 1.508(3) . ?
C6A H6A 0.9500 . ?
C7A H71A 0.9800 . ?
C7A H72A 0.9800 . ?
C7A H73A 0.9800 . ?
C8A H81A 0.9800 . ?
C8A H82A 0.9800 . ?
C8A H83A 0.9800 . ?
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
O1B H1B N1A 0.84 1.93 2.631(2) 140.8 . yes
C2A H2A Cl6B 0.95 2.88 3.720(2) 148.7 3 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
O1B C1B C2B C3B -179.60(15) . . . . ?
C6B C1B C2B C3B 1.7(2) . . . . ?
O1B C1B C2B Cl2B 0.6(2) . . . . ?
C6B C1B C2B Cl2B -178.08(12) . . . . ?
C1B C2B C3B C4B -1.5(2) . . . . ?
Cl2B C2B C3B C4B 178.35(13) . . . . ?
C1B C2B C3B Cl3B 179.15(13) . . . . ?
Cl2B C2B C3B Cl3B -1.0(2) . . . . ?
C2B C3B C4B C5B 0.2(2) . . . . ?
Cl3B C3B C4B C5B 179.61(13) . . . . ?
C3B C4B C5B C6B 0.7(2) . . . . ?
C3B C4B C5B Cl5B -179.47(13) . . . . ?
C4B C5B C6B C1B -0.4(2) . . . . ?
Cl5B C5B C6B C1B 179.78(13) . . . . ?
C4B C5B C6B Cl6B 179.50(13) . . . . ?
Cl5B C5B C6B Cl6B -0.3(2) . . . . ?
O1B C1B C6B C5B -179.58(15) . . . . ?
C2B C1B C6B C5B -0.8(2) . . . . ?
O1B C1B C6B Cl6B 0.5(2) . . . . ?
C2B C1B C6B Cl6B 179.28(12) . . . . ?
C6A N1A C2A C3A 0.9(3) . . . . ?
N1A C2A C3A C4A -0.5(3) . . . . ?
N1A C2A C3A C7A 179.47(17) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C7A C3A C4A C5A 179.67(16) . . . . ?
C3A C4A C5A C6A 0.7(2) . . . . ?
C3A C4A C5A C8A -179.74(16) . . . . ?
C2A N1A C6A C5A -0.5(3) . . . . ?
C4A C5A C6A N1A -0.3(3) . . . . ?
C8A C5A C6A N1A -179.83(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341381
