#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:32:25 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/12/7231247.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_7231247
loop_
_publ_author_name
'Kwon, Hyunchul'
'Lee, Eunsung'
_publ_section_title
;
 Coordination preference of hexa(2-pyridyl)benzene with copper(ii)
 directed by hydrogen bonding
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              5233
_journal_paper_doi               10.1039/C8CE00918J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C36 H28 Cl4 Cu2 N6 O2, 5.5(H2 O)'
_chemical_formula_sum            'C36 H39 Cl4 Cu2 N6 O7.5'
_chemical_formula_weight         944.61
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-07-17 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                113.957(18)
_cell_angle_beta                 111.576(17)
_cell_angle_gamma                91.514(16)
_cell_formula_units_Z            1
_cell_length_a                   9.081(5)
_cell_length_b                   10.926(6)
_cell_length_c                   12.055(7)
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.228
_cell_measurement_theta_min      2.031
_cell_volume                     994.5(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27505
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.228
_diffrn_reflns_theta_max         25.228
_diffrn_reflns_theta_min         2.031
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1537 before and 0.0926 after correction.
The Ratio of minimum to maximum transmission is 0.6473.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             483
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0580
_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)+(0.0557P)²+3.7812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2859
_reflns_number_total             3561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00918j2.cif
_cod_data_source_block           p-1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7231245--7231248.cif.'
_cod_original_cell_volume        994.5(9)
_cod_original_formula_sum        'C36 H39 Cl4 Cu2 N6 O7.50'
_cod_database_code               7231247
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.01
 O4-H4A
 0.95 with sigma of 0.01
 O4-H4B
 0.95 with sigma of 0.01
 O2-H2A
 1 with sigma of 0.02
 H1A-H1B
 1.34 with sigma of 0.02
3. Others
 Fixed Sof: O4(0.75) H4A(0.75) H4B(0.75)
4.a Free rotating group:
 O2(H2A,H2B), O4(H4A,H4B), O3(H3A,H3B)
4.b Rotating group:
 O1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C9(H9), C12(H12), C2(H2), C15(H15), C10(H10),
 C11(H11), C16(H16), C18(H18), C17(H17)
;
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.22485(7) 0.60597(6) 0.34747(6) 0.0254(2) Uani 1 1 d . . . .
Cl1 Cl 0.35923(17) 0.69896(15) 0.24979(16) 0.0418(4) Uani 1 1 d . . . .
Cl2 Cl 0.18842(18) 0.37379(14) 0.23557(16) 0.0432(4) Uani 1 1 d . . . .
N1 N -0.0099(4) 0.5985(4) 0.2390(4) 0.0198(8) Uani 1 1 d . . . .
O1 O 0.4244(4) 0.6097(4) 0.4994(4) 0.0389(9) Uani 1 1 d D . . .
H1A H 0.427046 0.671262 0.592274 0.058 Uiso 1 1 d DGR . . .
H1B H 0.487971 0.632618 0.468239 0.058 Uiso 1 1 d DGR . . .
N2 N 0.2132(4) 0.7864(4) 0.4880(4) 0.0215(9) Uani 1 1 d . . . .
N3 N -0.3962(5) 0.2814(4) 0.2570(4) 0.0285(10) Uani 1 1 d . . . .
O2 O 0.7140(6) 0.7723(5) 0.5699(5) 0.0589(13) Uani 1 1 d D . . .
H2A H 0.728047 0.718751 0.628808 0.088 Uiso 1 1 d DG . . .
H2B H 0.714722 0.836214 0.656096 0.088 Uiso 1 1 d G . . .
C5 C -0.1183(5) 0.5813(4) 0.2873(4) 0.0179(10) Uani 1 1 d . . . .
C6 C -0.0580(5) 0.5410(4) 0.3986(4) 0.0168(9) Uani 1 1 d . . . .
C7 C 0.0636(5) 0.6306(4) 0.5239(4) 0.0177(9) Uani 1 1 d . . . .
C13 C -0.1226(5) 0.4107(4) 0.3753(4) 0.0180(9) Uani 1 1 d . . . .
C8 C 0.1241(5) 0.7732(4) 0.5518(5) 0.0200(10) Uani 1 1 d . . . .
C1 C -0.0608(6) 0.6210(5) 0.1314(5) 0.0234(10) Uani 1 1 d . . . .
H1 H 0.013306 0.632704 0.098125 0.028 Uiso 1 1 calc R . . .
C4 C -0.2772(5) 0.5951(4) 0.2328(5) 0.0199(10) Uani 1 1 d . . . .
H4 H -0.348077 0.588386 0.270436 0.024 Uiso 1 1 calc R . . .
C3 C -0.3280(6) 0.6190(4) 0.1213(5) 0.0218(10) Uani 1 1 d . . . .
H3 H -0.433597 0.629104 0.083459 0.026 Uiso 1 1 calc R . . .
C14 C -0.2594(5) 0.3168(4) 0.2454(5) 0.0198(10) Uani 1 1 d . . . .
C9 C 0.0949(6) 0.8868(5) 0.6421(5) 0.0255(11) Uani 1 1 d . . . .
H9 H 0.033015 0.876019 0.685477 0.031 Uiso 1 1 calc R . . .
C12 C 0.2771(6) 0.9119(5) 0.5144(5) 0.0290(11) Uani 1 1 d . . . .
H12 H 0.339311 0.920701 0.470593 0.035 Uiso 1 1 calc R . . .
C2 C -0.2208(6) 0.6276(5) 0.0671(5) 0.0244(11) Uani 1 1 d . . . .
H2 H -0.254610 0.637684 -0.010947 0.029 Uiso 1 1 calc R . . .
C15 C -0.2490(7) 0.2703(5) 0.1252(5) 0.0310(12) Uani 1 1 d . . . .
H15 H -0.154062 0.294455 0.119396 0.037 Uiso 1 1 calc R . . .
C10 C 0.1591(6) 1.0163(5) 0.6668(5) 0.0283(11) Uani 1 1 d . . . .
H10 H 0.138099 1.093572 0.724802 0.034 Uiso 1 1 calc R . . .
C11 C 0.2543(6) 1.0291(5) 0.6045(5) 0.0335(13) Uani 1 1 d . . . .
H11 H 0.302594 1.115121 0.622582 0.040 Uiso 1 1 calc R . . .
C16 C -0.3911(8) 0.1825(5) 0.0081(5) 0.0369(14) Uani 1 1 d . . . .
H16 H -0.391223 0.147821 -0.076300 0.044 Uiso 1 1 calc R . . .
O4 O 0.9476(7) 0.9113(6) 1.0369(6) 0.0535(15) Uani 0.75 1 d D P . .
H4A H 0.944732 0.800472 0.986670 0.080 Uiso 0.75 1 d DG P . .
H4B H 0.976323 0.974419 1.005749 0.080 Uiso 0.75 1 d DG P . .
C18 C -0.5255(6) 0.1992(5) 0.1464(6) 0.0357(13) Uani 1 1 d . . . .
H18 H -0.618563 0.174057 0.154135 0.043 Uiso 1 1 calc R . . .
C17 C -0.5261(7) 0.1516(5) 0.0250(6) 0.0366(13) Uani 1 1 d . . . .
H17 H -0.619983 0.096534 -0.049292 0.044 Uiso 1 1 calc R . . .
O3 O 0.7777(12) 1.0383(6) 0.7583(6) 0.114(3) Uani 1 1 d . . A 2
H3A H 0.728776 1.101145 0.749117 0.171 Uiso 1 1 d G . A 2
H3B H 0.878414 1.055138 0.824173 0.171 Uiso 1 1 d G . A 2
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'
O O 0.0106 0.0060 '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
H3Ab O3b H3B 123.4 .
Cl2 Cu1 Cl1 105.69(7) .
N1 Cu1 Cl1 100.80(12) .
N1 Cu1 Cl2 90.94(11) .
N1 Cu1 O1 159.57(16) .
N1 Cu1 N2 85.29(15) .
O1 Cu1 Cl1 98.50(13) .
O1 Cu1 Cl2 90.27(12) .
O1 Cu1 N2 85.24(16) .
N2 Cu1 Cl1 98.61(12) .
N2 Cu1 Cl2 155.68(12) .
C5 N1 Cu1 116.8(3) .
C1 N1 Cu1 124.2(3) .
C1 N1 C5 118.7(4) .
Cu1 O1 H1A 112.6 .
Cu1 O1 H1B 91.2 .
H1A O1 H1B 123.0 .
C8 N2 Cu1 114.9(3) .
C12 N2 Cu1 126.0(3) .
C12 N2 C8 119.0(4) .
C18 N3 C14 118.6(5) .
H2A O2 H2B 72.1 .
N1 C5 C6 116.0(4) .
N1 C5 C4 121.7(4) .
C4 C5 C6 122.2(4) .
C7 C6 C5 121.0(4) .
C13 C6 C5 118.9(4) .
C13 C6 C7 120.0(4) .
C6 C7 C8 120.0(4) .
C13 C7 C6 120.2(4) 2_566
C13 C7 C8 119.7(4) 2_566
C6 C13 C14 120.9(4) .
C7 C13 C6 119.7(4) 2_566
C7 C13 C14 119.3(4) 2_566
N2 C8 C7 116.5(4) .
N2 C8 C9 121.4(4) .
C9 C8 C7 122.0(4) .
N1 C1 H1 118.8 .
N1 C1 C2 122.4(4) .
C2 C1 H1 118.8 .
C5 C4 H4 120.6 .
C3 C4 C5 118.8(4) .
C3 C4 H4 120.6 .
C4 C3 H3 120.3 .
C2 C3 C4 119.5(4) .
C2 C3 H3 120.3 .
N3 C14 C13 114.1(4) .
N3 C14 C15 122.6(4) .
C15 C14 C13 123.3(4) .
C8 C9 H9 120.4 .
C10 C9 C8 119.1(5) .
C10 C9 H9 120.4 .
N2 C12 H12 118.8 .
N2 C12 C11 122.4(5) .
C11 C12 H12 118.8 .
C1 C2 H2 120.6 .
C3 C2 C1 118.7(4) .
C3 C2 H2 120.6 .
C14 C15 H15 121.4 .
C14 C15 C16 117.2(5) .
C16 C15 H15 121.4 .
C9 C10 H10 120.5 .
C11 C10 C9 119.1(5) .
C11 C10 H10 120.5 .
C12 C11 H11 120.6 .
C10 C11 C12 118.9(5) .
C10 C11 H11 120.6 .
C15 C16 H16 121.1 .
C17 C16 C15 117.9(5) .
C17 C16 H16 121.1 .
H4A O4 H4B 121.5 .
N3 C18 H18 118.8 .
N3 C18 C17 122.5(5) .
C17 C18 H18 118.8 .
C16 C17 H17 119.4 .
C18 C17 C16 121.2(5) .
C18 C17 H17 119.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.4230(17) .
Cu1 Cl2 2.283(2) .
Cu1 N1 2.029(4) .
Cu1 O1 2.033(4) .
Cu1 N2 2.049(4) .
O3b H3A 0.8503 .
O3b H3B 0.9161 .
N1 C5 1.358(6) .
N1 C1 1.334(6) .
O1 H1A 1.0358 .
O1 H1B 0.8754 .
N2 C8 1.345(6) .
N2 C12 1.336(6) .
N3 C14 1.363(6) .
N3 C18 1.335(7) .
O2 H2A 1.0663 .
O2 H2B 0.9862 .
C5 C6 1.499(6) .
C5 C4 1.389(6) .
C6 C7 1.406(6) .
C6 C13 1.400(6) .
C7 C13 1.395(6) 2_566
C7 C8 1.495(6) .
C13 C7 1.395(6) 2_566
C13 C14 1.498(6) .
C8 C9 1.389(7) .
C1 H1 0.9300 .
C1 C2 1.393(7) .
C4 H4 0.9300 .
C4 C3 1.387(7) .
C3 H3 0.9300 .
C3 C2 1.377(7) .
C14 C15 1.368(7) .
C9 H9 0.9300 .
C9 C10 1.385(7) .
C12 H12 0.9300 .
C12 C11 1.383(7) .
C2 H2 0.9300 .
C15 H15 0.9300 .
C15 C16 1.440(8) .
C10 H10 0.9300 .
C10 C11 1.374(8) .
C11 H11 0.9300 .
C16 H16 0.9300 .
C16 C17 1.370(8) .
O4 H4A 1.1069 .
O4 H4B 0.9785 .
C18 H18 0.9300 .
C18 C17 1.337(8) .
C17 H17 0.9300 .
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
O1 H1A N3_$1 1.04 1.81 2.799(6) 158.9 2_566
O1 H1B O2 0.88 2.12 2.771(6) 130.3 .
