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#$Date: 2020-09-10 04:43:01 +0300 (Thu, 10 Sep 2020) $
#$Revision: 256291 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/11/7241199.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_7241199
loop_
_publ_author_name
'Rok, Magdalena'
'Moskwa, Marcin'
'Dopieralski, Przemyslaw'
'Medycki, Wojciech'
'Zamponi, Michaela'
'Bator, Grazyna'
_publ_section_title
;
 The influence of structure on the methyl group dynamics of the
 polymorphic complexes: 6,6'-dimethyl-2,2'-dipyridyl with halo derivatives
 of benzoquinone acids
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00973C
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 N2, C6 H Br2 O4'
_chemical_formula_sum            'C18 H14 Br2 N2 O4'
_chemical_formula_weight         482.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.252(4)
_cell_length_b                   11.926(2)
_cell_length_c                   10.272(4)
_cell_measurement_reflns_used    8943
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.1540
_cell_measurement_theta_min      3.3870
_cell_volume                     1768.4(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16895
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.495
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.611
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_correction_T_min  0.363
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0429
_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)+(0.0716P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2826
_reflns_number_total             3297
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00973c2.cif
_cod_data_source_block           1a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1768(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241199
_shelx_shelxl_version_number     2014/7
_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   0.248
_shelx_estimated_absorpt_t_max   0.475
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.09540(2) 0.27135(3) 0.65888(4) 0.02337(15) Uani 1 1 d . . . . .
Br2 Br 0.41193(2) 0.29420(3) 0.33946(4) 0.02057(15) Uani 1 1 d . . . . .
C1 C 0.1852(2) 0.2776(3) 0.5684(4) 0.0175(7) Uani 1 1 d . . . . .
C2 C 0.2076(2) 0.3753(3) 0.5214(4) 0.0182(7) Uani 1 1 d . . . . .
O2 O 0.16582(18) 0.4706(2) 0.5332(3) 0.0260(6) Uani 1 1 d . . . . .
H2 H 0.182(3) 0.533(4) 0.483(4) 0.039 Uiso 1 1 d . U . . .
C3 C 0.2834(2) 0.3827(3) 0.4556(3) 0.0176(7) Uani 1 1 d . . . . .
O3 O 0.30582(18) 0.48059(19) 0.4314(3) 0.0250(6) Uani 1 1 d . . . . .
C4 C 0.3222(2) 0.2835(3) 0.4298(4) 0.0163(7) Uani 1 1 d . . . . .
C5 C 0.3015(2) 0.1771(3) 0.4732(4) 0.0205(7) Uani 1 1 d . . . . .
O5 O 0.33810(18) 0.0877(2) 0.4596(3) 0.0312(6) Uani 1 1 d . . . . .
C6 C 0.2264(2) 0.1721(3) 0.5457(4) 0.0196(7) Uani 1 1 d . . . . .
O6 O 0.20468(18) 0.0816(2) 0.5790(3) 0.0310(6) Uani 1 1 d . . . . .
N11 N 0.33307(19) 0.6461(2) 0.6165(3) 0.0188(6) Uani 1 1 d . . . . .
H11 H 0.314(2) 0.584(3) 0.542(4) 0.023 Uiso 1 1 d . U . . .
C12 C 0.2905(2) 0.7470(3) 0.5874(4) 0.0216(8) Uani 1 1 d . . . . .
C13 C 0.3183(2) 0.8328(3) 0.6835(4) 0.0254(8) Uani 1 1 d . . . . .
H13 H 0.2899 0.9046 0.6653 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3881(3) 0.8118(4) 0.8064(4) 0.0299(9) Uani 1 1 d . . . . .
H14 H 0.4077 0.8695 0.8732 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4294(3) 0.7068(3) 0.8325(4) 0.0268(8) Uani 1 1 d . . . . .
H15 H 0.4771 0.6924 0.9170 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4006(2) 0.6236(3) 0.7345(4) 0.0225(8) Uani 1 1 d . . . . .
C17 C 0.4426(3) 0.5085(3) 0.7539(4) 0.0274(8) Uani 1 1 d . . . . .
H17A H 0.4027 0.4570 0.7836 0.041 Uiso 1 1 calc R U . . .
H17B H 0.5040 0.5112 0.8241 0.041 Uiso 1 1 calc R U . . .
H17C H 0.4486 0.4821 0.6668 0.041 Uiso 1 1 calc R U . . .
N21 N 0.17047(19) 0.6635(2) 0.3982(3) 0.0200(6) Uani 1 1 d . . . . .
C22 C 0.2166(2) 0.7581(3) 0.4535(4) 0.0200(7) Uani 1 1 d . . . . .
C23 C 0.1991(3) 0.8610(3) 0.3870(4) 0.0286(9) Uani 1 1 d . . . . .
H23 H 0.2325 0.9262 0.4281 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1320(3) 0.8662(3) 0.2598(4) 0.0334(9) Uani 1 1 d . . . . .
H24 H 0.1173 0.9358 0.2127 0.040 Uiso 1 1 calc R U . . .
C25 C 0.0859(3) 0.7695(4) 0.2009(5) 0.0327(9) Uani 1 1 d . . . . .
H25 H 0.0406 0.7718 0.1121 0.039 Uiso 1 1 calc R U . . .
C26 C 0.1064(2) 0.6689(3) 0.2728(4) 0.0239(8) Uani 1 1 d . . . . .
C27 C 0.0589(3) 0.5602(4) 0.2143(4) 0.0364(10) Uani 1 1 d . . . . .
H27A H 0.1021 0.5125 0.1865 0.055 Uiso 1 1 calc R U . . .
H27B H 0.0046 0.5762 0.1342 0.055 Uiso 1 1 calc R U . . .
H27C H 0.0393 0.5214 0.2844 0.055 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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 121.1(3) . . ?
C2 C1 Br1 121.3(3) . . ?
C6 C1 Br1 117.6(2) . . ?
O2 C2 C1 121.5(3) . . ?
O2 C2 C3 116.6(3) . . ?
C1 C2 C3 121.9(3) . . ?
C2 O2 H2 113(2) . . ?
O3 C3 C4 126.3(3) . . ?
O3 C3 C2 115.8(3) . . ?
C4 C3 C2 118.0(3) . . ?
C3 C4 C5 123.6(3) . . ?
C3 C4 Br2 117.2(2) . . ?
C5 C4 Br2 119.1(2) . . ?
O5 C5 C4 125.7(3) . . ?
O5 C5 C6 116.9(3) . . ?
C4 C5 C6 117.3(3) . . ?
O6 C6 C1 123.6(3) . . ?
O6 C6 C5 118.7(3) . . ?
C1 C6 C5 117.8(3) . . ?
C16 N11 C12 123.4(3) . . ?
C16 N11 H11 118(2) . . ?
C12 N11 H11 118(2) . . ?
N11 C12 C13 118.9(3) . . ?
N11 C12 C22 116.9(3) . . ?
C13 C12 C22 124.1(3) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N11 C16 C15 119.1(3) . . ?
N11 C16 C17 118.3(3) . . ?
C15 C16 C17 122.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 N21 C22 118.7(3) . . ?
N21 C22 C23 122.6(4) . . ?
N21 C22 C12 116.9(3) . . ?
C23 C22 C12 120.4(3) . . ?
C24 C23 C22 118.2(4) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N21 C26 C25 121.3(3) . . ?
N21 C26 C27 116.5(3) . . ?
C25 C26 C27 122.1(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
Br1 C1 1.888(4) . ?
Br2 C4 1.890(3) . ?
C1 C2 1.348(5) . ?
C1 C6 1.459(5) . ?
C2 O2 1.327(4) . ?
C2 C3 1.518(5) . ?
O2 H2 0.99(4) . ?
C3 O3 1.264(4) . ?
C3 C4 1.387(5) . ?
C4 C5 1.414(5) . ?
C5 O5 1.232(4) . ?
C5 C6 1.555(5) . ?
C6 O6 1.211(4) . ?
N11 C16 1.340(5) . ?
N11 C12 1.354(4) . ?
N11 H11 1.04(4) . ?
C12 C13 1.390(5) . ?
C12 C22 1.476(6) . ?
C13 C14 1.387(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.501(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.344(5) . ?
N21 C22 1.354(5) . ?
C22 C23 1.388(5) . ?
C23 C24 1.377(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.512(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
O2 H2 N21 0.99(4) 1.76(4) 2.698(4) 157(4) .
N11 H11 O3 1.04(4) 1.65(4) 2.678(4) 169(3) .
C13 H13 O6 0.95 2.49 3.428(4) 170.8 1_565
C15 H15 Br2 0.95 2.80 3.609(4) 143.1 2_656
C17 H17A O5 0.98 2.38 3.239(5) 145.8 4_566
C23 H23 O5 0.95 2.46 3.367(4) 158.7 1_565
C23 H23 O6 0.95 2.54 3.272(5) 134.2 1_565
C25 H25 Br1 0.95 2.89 3.835(5) 178.1 2
C27 H27A O6 0.98 2.46 3.425(5) 168.8 4_565
