#------------------------------------------------------------------------------
#$Date: 2020-09-10 03:43:01 +0200 (jue 10 de sep de 2020) $
#$Revision: 256291 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/12/7241201.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_7241201
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, 0.5(C6 Br2 O4)'
_chemical_formula_sum            'C15 H13 Br N2 O2'
_chemical_formula_weight         333.18
_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   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                94.41(4)
_cell_angle_beta                 106.41(5)
_cell_angle_gamma                110.28(3)
_cell_formula_units_Z            2
_cell_length_a                   7.792(4)
_cell_length_b                   9.705(3)
_cell_length_c                   9.938(5)
_cell_measurement_reflns_used    2787
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5940
_cell_measurement_theta_min      3.4340
_cell_volume                     663.3(6)
_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      100(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3927
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.496
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.641
_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            red
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0148P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2252
_reflns_number_total             2436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00973c2.cif
_cod_data_source_block           2a
_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        663(3)
_cod_database_code               7241201
_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   0.511
_shelx_estimated_absorpt_t_max   0.689
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
Br1 Br 0.82164(3) 0.35340(3) 1.11080(2) 0.01404(8) Uani 1 1 d . . . . .
C1 C 0.6417(3) 0.1509(3) 1.0454(2) 0.0116(5) Uani 1 1 d . . . . .
C2 C 0.6617(3) 0.0473(3) 1.1348(2) 0.0112(5) Uani 1 1 d . . . . .
O2 O 0.7912(2) 0.07444(18) 1.25107(17) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.4915(3) 0.1161(3) 0.9155(2) 0.0114(5) Uani 1 1 d . . . . .
O3 O 0.4678(2) 0.20526(18) 0.83468(17) 0.0151(4) Uani 1 1 d . . . . .
N21 N 0.2587(3) 0.3479(2) 0.39984(19) 0.0125(4) Uani 1 1 d . . . . .
C22 C 0.2225(3) 0.2426(3) 0.4794(2) 0.0122(5) Uani 1 1 d . . . . .
C23 C 0.2858(3) 0.1249(3) 0.4782(2) 0.0135(5) Uani 1 1 d . . . . .
H23 H 0.2588 0.0534 0.5373 0.016 Uiso 1 1 calc R U . . .
C24 C 0.3895(3) 0.1162(3) 0.3878(2) 0.0159(5) Uani 1 1 d . . . . .
H24 H 0.4349 0.0374 0.3834 0.019 Uiso 1 1 calc R U . . .
C25 C 0.4264(3) 0.2229(3) 0.3039(3) 0.0159(5) Uani 1 1 d . . . . .
H25 H 0.4966 0.2177 0.2409 0.019 Uiso 1 1 calc R U . . .
C26 C 0.3598(3) 0.3382(3) 0.3128(2) 0.0138(5) Uani 1 1 d . . . . .
C27 C 0.3968(4) 0.4581(3) 0.2249(3) 0.0185(5) Uani 1 1 d . . . . .
H27A H 0.2737 0.4490 0.1557 0.028 Uiso 1 1 calc R U . . .
H27B H 0.4833 0.4465 0.1739 0.028 Uiso 1 1 calc R U . . .
H27C H 0.4576 0.5568 0.2880 0.028 Uiso 1 1 calc R U . . .
N11 N 0.1245(3) 0.2090(2) 0.6916(2) 0.0116(4) Uani 1 1 d . . . . .
H11 H 0.221(4) 0.181(3) 0.724(3) 0.014 Uiso 1 1 d . U . . .
C12 C 0.1022(3) 0.2585(2) 0.5669(2) 0.0117(5) Uani 1 1 d . . . . .
C13 C -0.0358(3) 0.3200(3) 0.5232(2) 0.0127(5) Uani 1 1 d . . . . .
H13 H -0.0555 0.3542 0.4352 0.015 Uiso 1 1 calc R U . . .
C14 C -0.1444(3) 0.3310(3) 0.6088(2) 0.0142(5) Uani 1 1 d . . . . .
H14 H -0.2360 0.3762 0.5812 0.017 Uiso 1 1 calc R U . . .
C15 C -0.1206(3) 0.2765(3) 0.7348(2) 0.0144(5) Uani 1 1 d . . . . .
H15 H -0.1975 0.2818 0.7925 0.017 Uiso 1 1 calc R U . . .
C16 C 0.0174(3) 0.2139(3) 0.7757(2) 0.0139(5) Uani 1 1 d . . . . .
C17 C 0.0528(4) 0.1489(3) 0.9078(3) 0.0213(6) Uani 1 1 d . . . . .
H17A H 0.0152 0.0407 0.8808 0.032 Uiso 1 1 calc R U . . .
H17B H -0.0242 0.1682 0.9641 0.032 Uiso 1 1 calc R U . . .
H17C H 0.1907 0.1954 0.9649 0.032 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
C3 C1 C2 124.0(2) . . ?
C3 C1 Br1 117.86(18) . . ?
C2 C1 Br1 117.99(17) . . ?
O2 C2 C1 125.9(2) . . ?
O2 C2 C3 116.3(2) . 2_657 ?
C1 C2 C3 117.9(2) . 2_657 ?
O3 C3 C1 125.8(2) . . ?
O3 C3 C2 116.1(2) . 2_657 ?
C1 C3 C2 118.1(2) . 2_657 ?
C22 N21 C26 118.1(2) . . ?
N21 C22 C23 123.8(2) . . ?
N21 C22 C12 114.2(2) . . ?
C23 C22 C12 121.9(2) . . ?
C24 C23 C22 117.5(2) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C23 C24 C25 119.5(2) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 119.4(2) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N21 C26 C25 121.7(2) . . ?
N21 C26 C27 116.5(2) . . ?
C25 C26 C27 121.7(2) . . ?
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 . . ?
C16 N11 C12 123.5(2) . . ?
C16 N11 H11 117.9(17) . . ?
C12 N11 H11 118.4(17) . . ?
N11 C12 C13 118.8(2) . . ?
N11 C12 C22 119.3(2) . . ?
C13 C12 C22 121.9(2) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N11 C16 C15 118.8(2) . . ?
N11 C16 C17 117.4(2) . . ?
C15 C16 C17 123.8(2) . . ?
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 . . ?
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 1.905(3) . ?
C1 C3 1.398(3) . ?
C1 C2 1.411(3) . ?
C2 O2 1.238(3) . ?
C2 C3 1.555(3) 2_657 ?
C3 O3 1.250(3) . ?
C3 C2 1.555(3) 2_657 ?
N21 C22 1.341(3) . ?
N21 C26 1.342(3) . ?
C22 C23 1.393(3) . ?
C22 C12 1.483(3) . ?
C23 C24 1.383(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.505(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N11 C16 1.346(3) . ?
N11 C12 1.351(3) . ?
N11 H11 0.87(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.497(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
N11 H11 O2 0.87(3) 2.48(3) 3.099(3) 129(2) 2_657
N11 H11 O3 0.87(3) 1.85(3) 2.665(3) 155(2) .
C17 H17B Br1 0.98 2.98 3.895(3) 155.8 1_455
C23 H23 O2 0.95 2.58 3.500(3) 163.9 2_657
C25 H25 Br1 0.95 3.10 3.973(3) 153.2 1_554
C27 H27C O3 0.98 2.66 3.225(3) 117.2 2_666
C13 H13 Br1 0.95 3.09 4.002(3) 161.1 1_454
C15 H15 Br1 0.95 3.14 3.934(3) 142.7 1_455
C15 H15 O3 0.95 2.62 3.481(3) 151.4 1_455
