#------------------------------------------------------------------------------
#$Date: 2019-11-17 11:41:21 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229656 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/65/7046532.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_7046532
loop_
_publ_author_name
'Kwon, Hyunchul'
'Lee, Eunsung'
_publ_section_title
;
 Static and dynamic coordination behaviours of copper(i) ions in
 hexa(2-pyridyl)benzene ligand systems.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8448
_journal_page_last               8455
_journal_paper_doi               10.1039/c8dt01424h
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C23 H21 Cl Cu N4, C2 H3 N'
_chemical_formula_sum            'C25 H24 Cl Cu N5'
_chemical_formula_weight         493.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-07 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                106.64(3)
_cell_angle_beta                 94.63(3)
_cell_angle_gamma                108.42(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9830(18)
_cell_length_b                   12.124(2)
_cell_length_c                   12.321(3)
_cell_measurement_reflns_used    4255
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.020
_cell_measurement_theta_min      2.105
_cell_volume                     1198.0(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7059
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.105
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.528
_refine_diff_density_min         -1.349
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0347
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3944
_reflns_number_total             4255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01424h2.cif
_cod_data_source_block           p-1
_cod_depositor_comments
'Adding full bibliography for 7046531--7046536.cif.'
_cod_original_cell_volume        1198.0(5)
_cod_database_code               7046532
_shelx_shelxl_version_number     2016/4
_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   0.903
_shelx_estimated_absorpt_t_min   0.903
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C11(H11), C12(H12), C14(H14), C16(H16), C17(H17),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C25(H25A,H25B,H25C)
;
_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
Cu1 Cu 0.27256(3) 0.67476(2) 0.38760(2) 0.01189(14) Uani 1 1 d .
Cl2 Cl 0.14830(6) 0.77531(5) 0.29991(4) 0.01661(17) Uani 1 1 d .
N1 N 0.3008(2) 0.54257(17) 0.24696(14) 0.0113(4) Uani 1 1 d .
N2 N 0.8577(2) 0.72540(17) 0.71247(14) 0.0117(4) Uani 1 1 d .
N3 N 0.5161(2) 0.77515(17) 0.41960(14) 0.0107(4) Uani 1 1 d .
N4 N 0.1953(2) 0.62727(17) 0.51589(15) 0.0152(4) Uani 1 1 d .
C1 C 0.6911(3) 0.8395(2) 0.68598(17) 0.0145(4) Uani 1 1 d .
H1 H 0.593464 0.840281 0.650935 0.017 Uiso 1 1 calc R
C2 C 0.7223(2) 0.7304(2) 0.66197(16) 0.0107(4) Uani 1 1 d .
C3 C 0.6071(2) 0.61195(19) 0.57808(16) 0.0097(4) Uani 1 1 d .
C4 C 0.4331(2) 0.4018(2) 0.17290(18) 0.0134(4) Uani 1 1 d .
H4 H 0.500144 0.358523 0.186970 0.016 Uiso 1 1 calc R
C5 C 0.5560(2) 0.60366(19) 0.46431(16) 0.0097(4) Uani 1 1 d .
C6 C 0.3942(2) 0.4791(2) 0.26436(16) 0.0100(4) Uani 1 1 d .
C7 C 0.5734(2) 0.8847(2) 0.40383(17) 0.0119(4) Uani 1 1 d .
H7 H 0.501601 0.926722 0.397729 0.014 Uiso 1 1 calc R
C8 C 0.2738(3) 0.4521(2) 0.04119(17) 0.0160(5) Uani 1 1 d .
C9 C 0.1576(2) 0.6008(2) 0.59350(17) 0.0135(4) Uani 1 1 d .
C10 C 0.4483(2) 0.4915(2) 0.38654(16) 0.0099(4) Uani 1 1 d .
C11 C 0.9637(3) 0.8298(2) 0.78679(17) 0.0161(5) Uani 1 1 d .
H11 H 1.057720 0.825764 0.824019 0.019 Uiso 1 1 calc R
C12 C 0.7756(2) 0.7617(2) 0.41580(16) 0.0121(4) Uani 1 1 d .
H12 H 0.844294 0.716516 0.418565 0.015 Uiso 1 1 calc R
C13 C 0.2014(3) 0.4385(3) -0.07834(19) 0.0250(5) Uani 1 1 d .
H13A H 0.104387 0.364766 -0.107074 0.037 Uiso 1 1 calc GR
H13B H 0.278264 0.430564 -0.129506 0.037 Uiso 1 1 calc GR
H13C H 0.174433 0.511167 -0.076428 0.037 Uiso 1 1 calc GR
C14 C 0.2434(2) 0.5283(2) 0.13725(17) 0.0137(4) Uani 1 1 d .
H14 H 0.177939 0.573439 0.125193 0.016 Uiso 1 1 calc R
C15 C 0.6183(2) 0.7154(2) 0.42946(16) 0.0103(4) Uani 1 1 d .
C16 C 0.3726(3) 0.3887(2) 0.06107(18) 0.0163(5) Uani 1 1 d .
H16 H 0.398631 0.336538 -0.002172 0.020 Uiso 1 1 calc R
C17 C 0.8047(3) 0.9469(2) 0.76173(18) 0.0184(5) Uani 1 1 d .
H17 H 0.786034 1.022345 0.778277 0.022 Uiso 1 1 calc R
C18 C 0.7316(3) 0.9408(2) 0.39583(16) 0.0136(4) Uani 1 1 d .
C19 C 0.8313(2) 0.8744(2) 0.39808(16) 0.0142(4) Uani 1 1 d .
H19 H 0.938120 0.906181 0.387451 0.017 Uiso 1 1 calc R
C20 C 0.9463(3) 0.9438(2) 0.81361(17) 0.0164(5) Uani 1 1 d .
C21 C 0.7861(3) 1.0675(2) 0.38554(19) 0.0199(5) Uani 1 1 d .
H21A H 0.751063 1.061848 0.306075 0.030 Uiso 1 1 calc GR
H21B H 0.902922 1.104073 0.405823 0.030 Uiso 1 1 calc GR
H21C H 0.739799 1.119253 0.438034 0.030 Uiso 1 1 calc GR
C22 C 0.1072(3) 0.5676(2) 0.69296(18) 0.0174(5) Uani 1 1 d .
H22A H 0.089346 0.480245 0.678928 0.026 Uiso 1 1 calc GR
H22B H 0.007907 0.582578 0.705238 0.026 Uiso 1 1 calc GR
H22C H 0.190564 0.617661 0.761584 0.026 Uiso 1 1 calc GR
N5 N 0.3657(3) 0.8296(3) -0.0893(2) 0.0461(7) Uani 1 1 d .
C23 C 1.0774(3) 1.0599(2) 0.8919(2) 0.0268(6) Uani 1 1 d .
H23A H 1.158022 1.037910 0.930503 0.040 Uiso 1 1 calc GR
H23B H 1.031748 1.106485 0.949958 0.040 Uiso 1 1 calc GR
H23C H 1.127229 1.110423 0.846120 0.040 Uiso 1 1 calc GR
C24 C 0.4042(3) 0.8482(3) 0.0060(2) 0.0327(6) Uani 1 1 d .
C25 C 0.4547(3) 0.8739(3) 0.1285(2) 0.0357(7) Uani 1 1 d .
H25A H 0.542836 0.844657 0.140039 0.054 Uiso 1 1 calc GR
H25B H 0.364848 0.831478 0.159427 0.054 Uiso 1 1 calc GR
H25C H 0.490441 0.962800 0.168674 0.054 Uiso 1 1 calc GR
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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
N1 Cu1 Cl2 102.61(5) .
N3 Cu1 Cl2 106.13(5) .
N3 Cu1 N1 89.81(8) .
N4 Cu1 Cl2 119.75(6) .
N4 Cu1 N1 119.36(8) .
N4 Cu1 N3 114.54(8) .
C6 N1 Cu1 119.57(13) .
C6 N1 C14 118.10(17) .
C14 N1 Cu1 121.89(14) .
C11 N2 C2 117.69(19) .
C7 N3 Cu1 122.18(13) .
C7 N3 C15 118.17(18) .
C15 N3 Cu1 117.74(15) .
C9 N4 Cu1 176.59(17) .
C2 C1 H1 120.5 .
C17 C1 H1 120.5 .
C17 C1 C2 119.0(2) .
N2 C2 C1 122.1(2) .
N2 C2 C3 116.24(18) .
C1 C2 C3 121.70(18) .
C5 C3 C2 120.47(18) .
C10 C3 C2 119.49(17) 2_666
C10 C3 C5 120.04(19) 2_666
C6 C4 H4 120.5 .
C16 C4 H4 120.5 .
C16 C4 C6 119.05(19) .
C3 C5 C10 119.68(19) .
C3 C5 C15 118.58(18) .
C10 C5 C15 121.74(17) .
N1 C6 C4 121.73(17) .
N1 C6 C10 116.74(17) .
C4 C6 C10 121.48(17) .
N3 C7 H7 117.9 .
N3 C7 C18 124.11(19) .
C18 C7 H7 117.9 .
C14 C8 C13 120.9(2) .
C14 C8 C16 116.88(18) .
C16 C8 C13 122.2(2) .
N4 C9 C22 179.1(2) .
C3 C10 C5 120.28(18) 2_666
C3 C10 C6 118.76(18) 2_666
C5 C10 C6 120.94(18) .
N2 C11 H11 117.7 .
N2 C11 C20 124.7(2) .
C20 C11 H11 117.7 .
C15 C12 H12 120.3 .
C19 C12 H12 120.3 .
C19 C12 C15 119.30(19) .
C8 C13 H13A 109.5 .
C8 C13 H13B 109.5 .
C8 C13 H13C 109.5 .
H13A C13 H13B 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N1 C14 C8 124.12(19) .
N1 C14 H14 117.9 .
C8 C14 H14 117.9 .
N3 C15 C5 116.30(18) .
N3 C15 C12 121.2(2) .
C12 C15 C5 122.32(18) .
C4 C16 C8 120.1(2) .
C4 C16 H16 119.9 .
C8 C16 H16 119.9 .
C1 C17 H17 120.1 .
C1 C17 C20 119.8(2) .
C20 C17 H17 120.1 .
C7 C18 C21 119.85(19) .
C19 C18 C7 116.7(2) .
C19 C18 C21 123.4(2) .
C12 C19 H19 119.9 .
C18 C19 C12 120.2(2) .
C18 C19 H19 119.9 .
C11 C20 C17 116.8(2) .
C11 C20 C23 121.6(2) .
C17 C20 C23 121.6(2) .
C18 C21 H21A 109.5 .
C18 C21 H21B 109.5 .
C18 C21 H21C 109.5 .
H21A C21 H21B 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C9 C22 H22A 109.5 .
C9 C22 H22B 109.5 .
C9 C22 H22C 109.5 .
H22A C22 H22B 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C20 C23 H23A 109.5 .
C20 C23 H23B 109.5 .
C20 C23 H23C 109.5 .
H23A C23 H23B 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
N5 C24 C25 179.2(4) .
C24 C25 H25A 109.5 .
C24 C25 H25B 109.5 .
C24 C25 H25C 109.5 .
H25A C25 H25B 109.5 .
H25A C25 H25C 109.5 .
H25B C25 H25C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl2 2.3063(8) .
Cu1 N1 2.0912(19) .
Cu1 N3 2.080(2) .
Cu1 N4 1.9386(19) .
N1 C6 1.347(3) .
N1 C14 1.349(2) .
N2 C2 1.348(3) .
N2 C11 1.334(3) .
N3 C7 1.341(3) .
N3 C15 1.354(3) .
N4 C9 1.136(3) .
C1 H1 0.9500 .
C1 C2 1.393(3) .
C1 C17 1.385(3) .
C2 C3 1.496(3) .
C3 C5 1.404(3) .
C3 C10 1.401(3) 2_666
C4 H4 0.9500 .
C4 C6 1.392(3) .
C4 C16 1.385(3) .
C5 C10 1.406(3) .
C5 C15 1.492(3) .
C6 C10 1.494(3) .
C7 H7 0.9500 .
C7 C18 1.394(3) .
C8 C13 1.502(3) .
C8 C14 1.384(3) .
C8 C16 1.394(3) .
C9 C22 1.458(3) .
C10 C3 1.402(3) 2_666
C11 H11 0.9500 .
C11 C20 1.389(3) .
C12 H12 0.9500 .
C12 C15 1.390(3) .
C12 C19 1.387(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14 0.9500 .
C16 H16 0.9500 .
C17 H17 0.9500 .
C17 C20 1.393(3) .
C18 C19 1.383(3) .
C18 C21 1.504(3) .
C19 H19 0.9500 .
C20 C23 1.513(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
N5 C24 1.132(4) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C25 1.453(4) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
