#------------------------------------------------------------------------------
#$Date: 2020-09-10 04:43:01 +0300 (Thu, 10 Sep 2020) $
#$Revision: 256291 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241200.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_7241200
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 I2 O4), 0.5(C6 H2 I2 O4)'
_chemical_formula_sum            'C18 H14 I2 N2 O4'
_chemical_formula_weight         576.11
_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                110.26(2)
_cell_angle_beta                 92.56(2)
_cell_angle_gamma                113.13(2)
_cell_formula_units_Z            2
_cell_length_a                   10.026(2)
_cell_length_b                   10.281(2)
_cell_length_c                   10.526(2)
_cell_measurement_reflns_used    12873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.8300
_cell_measurement_theta_min      3.3840
_cell_volume                     915.3(4)
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(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  0.0231
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.499
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.399
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.462
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_correction_T_min  0.555
_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    2.090
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0193
_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)+(0.0327P)²+0.6412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3239
_reflns_number_total             3402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00973c2.cif
_cod_data_source_block           3a
_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        915(4)
_cod_database_code               7241200
_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   0.466
_shelx_estimated_absorpt_t_max   0.625
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
I1A I 0.38166(2) 0.15099(2) 0.54957(2) 0.01384(7) Uani 1 1 d . . . . .
C1A C 0.4501(3) 0.3576(3) 0.5213(3) 0.0126(5) Uani 1 1 d . . . . .
O2A O 0.6561(2) 0.4912(2) 0.70995(19) 0.0160(4) Uani 1 1 d . . . . .
C2A C 0.5758(3) 0.4860(3) 0.6131(3) 0.0118(5) Uani 1 1 d . . . . .
O3A O 0.27530(19) 0.2437(2) 0.31186(19) 0.0153(4) Uani 1 1 d . . . . .
C3A C 0.3767(3) 0.3577(3) 0.4047(3) 0.0113(5) Uani 1 1 d . . . . .
I1B I 0.76243(2) 0.51676(2) 1.23857(2) 0.01386(7) Uani 1 1 d . . . . .
C1B C 0.8979(3) 0.5025(3) 1.0949(3) 0.0126(5) Uani 1 1 d . . . . .
O2B O 1.1161(2) 0.6254(2) 1.26917(19) 0.0179(4) Uani 1 1 d . . . . .
C2B C 1.0572(3) 0.5638(3) 1.1471(3) 0.0128(5) Uani 1 1 d . . . . .
O3B O 0.7010(2) 0.3954(2) 0.90505(19) 0.0155(4) Uani 1 1 d . . . . .
H3B H 0.6863 0.3845 0.8163 0.023 Uiso 1 1 d R U . . .
C3B C 0.8436(3) 0.4477(3) 0.9581(3) 0.0123(5) Uani 1 1 d . . . . .
N11 N 0.1235(2) 0.2234(2) 0.0717(2) 0.0118(4) Uani 1 1 d . . . . .
H11 H 0.1807 0.2607 0.1560 0.014 Uiso 1 1 d R U . . .
C12 C -0.0264(3) 0.1766(3) 0.0523(3) 0.0117(5) Uani 1 1 d . . . . .
C13 C -0.1067(3) 0.1099(3) -0.0827(3) 0.0136(5) Uani 1 1 d . . . . .
H13 H -0.2109 0.0772 -0.0996 0.016 Uiso 1 1 calc R U . . .
C14 C -0.0357(3) 0.0909(3) -0.1919(3) 0.0154(5) Uani 1 1 d . . . . .
H14 H -0.0914 0.0440 -0.2841 0.018 Uiso 1 1 calc R U . . .
C15 C 0.1167(3) 0.1399(3) -0.1682(3) 0.0132(5) Uani 1 1 d . . . . .
H15 H 0.1657 0.1261 -0.2436 0.016 Uiso 1 1 calc R U . . .
C16 C 0.1968(3) 0.2094(3) -0.0325(3) 0.0123(5) Uani 1 1 d . . . . .
C17 C 0.3616(3) 0.2686(3) 0.0043(3) 0.0175(6) Uani 1 1 d . . . . .
H17A H 0.4065 0.3797 0.0604 0.026 Uiso 1 1 calc R U . . .
H17B H 0.4006 0.2489 -0.0806 0.026 Uiso 1 1 calc R U . . .
H17C H 0.3857 0.2160 0.0573 0.026 Uiso 1 1 calc R U . . .
N21 N -0.2466(2) 0.1143(2) 0.1403(2) 0.0132(4) Uani 1 1 d . . . . .
C22 C -0.0968(3) 0.1962(3) 0.1737(3) 0.0123(5) Uani 1 1 d . . . . .
C23 C -0.0180(3) 0.2892(3) 0.3089(3) 0.0151(5) Uani 1 1 d . . . . .
H23 H 0.0862 0.3495 0.3284 0.018 Uiso 1 1 calc R U . . .
C24 C -0.0958(3) 0.2916(3) 0.4146(3) 0.0175(6) Uani 1 1 d . . . . .
H24 H -0.0449 0.3513 0.5085 0.021 Uiso 1 1 calc R U . . .
C25 C -0.2476(3) 0.2066(3) 0.3822(3) 0.0159(6) Uani 1 1 d . . . . .
H25 H -0.3024 0.2061 0.4535 0.019 Uiso 1 1 calc R U . . .
C26 C -0.3203(3) 0.1210(3) 0.2428(3) 0.0132(5) Uani 1 1 d . . . . .
C27 C -0.4867(3) 0.0333(3) 0.2017(3) 0.0177(6) Uani 1 1 d . . . . .
H27A H -0.5161 -0.0283 0.1017 0.027 Uiso 1 1 calc R U . . .
H27B H -0.5310 0.1061 0.2255 0.027 Uiso 1 1 calc R U . . .
H27C H -0.5212 -0.0348 0.2512 0.027 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'
I I -0.4742 1.8119 '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
C2A C1A C3A 122.9(2) . . ?
C2A C1A I1A 118.20(18) . . ?
C3A C1A I1A 118.61(18) . . ?
O2A C2A C1A 127.1(2) . . ?
O2A C2A C3A 114.8(2) . 2_666 ?
C1A C2A C3A 118.1(2) . 2_666 ?
O3A C3A C1A 125.9(2) . . ?
O3A C3A C2A 115.7(2) . 2_666 ?
C1A C3A C2A 118.4(2) . 2_666 ?
C3B C1B C2B 120.1(2) . . ?
C3B C1B I1B 121.68(19) . . ?
C2B C1B I1B 118.09(19) . . ?
O2B C2B C1B 124.1(2) . . ?
O2B C2B C3B 117.8(2) . 2_767 ?
C1B C2B C3B 118.1(2) . 2_767 ?
C3B O3B H3B 111.6 . . ?
O3B C3B C1B 122.9(2) . . ?
O3B C3B C2B 115.5(2) . 2_767 ?
C1B C3B C2B 121.6(2) . 2_767 ?
C16 N11 C12 123.6(2) . . ?
C16 N11 H11 114.2 . . ?
C12 N11 H11 122.1 . . ?
N11 C12 C13 117.8(2) . . ?
N11 C12 C22 119.5(2) . . ?
C13 C12 C22 122.7(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 119.0(2) . . ?
N11 C16 C17 117.7(2) . . ?
C15 C16 C17 123.3(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 . . ?
C26 N21 C22 118.1(2) . . ?
N21 C22 C23 123.0(2) . . ?
N21 C22 C12 113.4(2) . . ?
C23 C22 C12 123.5(2) . . ?
C24 C23 C22 118.1(2) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N21 C26 C25 122.0(2) . . ?
N21 C26 C27 116.7(2) . . ?
C25 C26 C27 121.3(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 . . ?
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
I1A C1A 2.093(3) . ?
C1A C2A 1.402(4) . ?
C1A C3A 1.403(4) . ?
O2A C2A 1.243(3) . ?
C2A C3A 1.569(3) 2_666 ?
O3A C3A 1.242(3) . ?
C3A C2A 1.569(3) 2_666 ?
I1B C1B 2.083(3) . ?
C1B C3B 1.347(4) . ?
C1B C2B 1.463(4) . ?
O2B C2B 1.215(3) . ?
C2B C3B 1.525(4) 2_767 ?
O3B C3B 1.327(3) . ?
O3B H3B 0.9000 . ?
C3B C2B 1.525(4) 2_767 ?
N11 C16 1.345(3) . ?
N11 C12 1.366(3) . ?
N11 H11 0.9000 . ?
C12 C13 1.388(4) . ?
C12 C22 1.478(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.498(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.332(3) . ?
N21 C22 1.357(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.505(4) . ?
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
C15 H15 I1A 0.95 3.14 4.074(3) 167.6 1_554
C23 H23 O3A 0.95 2.52 3.155(3) 124.7 .
N11 H11 O3A 0.90 1.95 2.791(3) 154.5 .
N11 H11 O2A 0.90 2.28 2.925(3) 128.4 2_666
O3B H3B O2A 0.90 1.90 2.657(3) 139.8 .
O3B H3B O2B 0.90 2.24 2.666(3) 108.8 2_767
