#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:22:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180075 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/21/7052159.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_7052159
loop_
_publ_author_name
'Liliana Dobrzańska'
'Gareth O. Lloyd'
'Leonard J. Barbour'
_publ_section_title
;
 The solvent-templating effect as the driving factor that influences
 the formation of crystalline materials based on the stacking of
 metallocycles
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              669
_journal_paper_doi               10.1039/b618495m
_journal_volume                  31
_journal_year                    2007
_chemical_formula_moiety         'C16 H18 Cl2 Cu N4, C2 H4 Cl2'
_chemical_formula_sum            'C18 H22 Cl4 Cu N4'
_chemical_formula_weight         499.74
_chemical_name_common            9
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.272(10)
_cell_angle_beta                 91.858(10)
_cell_angle_gamma                112.793(9)
_cell_formula_units_Z            2
_cell_length_a                   8.539(5)
_cell_length_b                   10.673(6)
_cell_length_c                   13.386(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1078.7(10)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  X-Seed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.1374
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6815
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  0.8155
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.064
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                2940
_reflns_number_total             4785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b618495m.txt
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052159
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.21831(9) 0.49966(7) 0.23990(6) 0.0156(2) Uani 1 1 d . . .
Cl1 Cl -0.02110(18) 0.51191(16) 0.17681(12) 0.0233(4) Uani 1 1 d . . .
N1 N 0.1649(6) 0.4568(5) 0.3722(4) 0.0156(10) Uani 1 1 d . . .
Cl2 Cl 0.46687(18) 0.69327(15) 0.30023(12) 0.0228(4) Uani 1 1 d . . .
C2 C 0.0276(7) 0.3532(6) 0.3888(4) 0.0165(12) Uani 1 1 d . . .
Cl3 Cl -0.1139(2) -0.0612(2) -0.16647(17) 0.0482(5) Uani 1 1 d . . .
N3 N 0.0444(6) 0.3537(5) 0.4890(4) 0.0169(11) Uani 1 1 d . . .
Cl4 Cl -0.4155(3) -0.1309(2) -0.36793(15) 0.0536(6) Uani 1 1 d . . .
C4 C 0.1988(7) 0.4605(6) 0.5391(5) 0.0214(14) Uani 1 1 d . . .
H4 H 0.2438 0.4855 0.6104 0.026 Uiso 1 1 calc R . .
C5 C 0.2735(8) 0.5228(6) 0.4665(5) 0.0196(13) Uani 1 1 d . . .
H5 H 0.3829 0.5996 0.4782 0.023 Uiso 1 1 calc R . .
C6 C -0.1202(7) 0.2493(6) 0.3097(5) 0.0213(14) Uani 1 1 d . . .
H6A H -0.1144 0.2791 0.2458 0.032 Uiso 1 1 calc R . .
H6B H -0.2274 0.2441 0.3363 0.032 Uiso 1 1 calc R . .
H6C H -0.1165 0.1559 0.2945 0.032 Uiso 1 1 calc R . .
C7 C -0.0747(7) 0.2494(6) 0.5362(5) 0.0188(13) Uani 1 1 d . . .
H7A H -0.1944 0.2222 0.5057 0.023 Uiso 1 1 calc R . .
H7B H -0.0628 0.2924 0.6121 0.023 Uiso 1 1 calc R . .
C8 C -0.0368(7) 0.1198(6) 0.5172(4) 0.0153(12) Uani 1 1 d . . .
C9 C 0.1151(8) 0.1274(6) 0.5636(5) 0.0207(14) Uani 1 1 d . . .
H9 H 0.1949 0.2151 0.6084 0.025 Uiso 1 1 calc R . .
C10 C 0.1526(7) 0.0101(6) 0.5462(5) 0.0213(14) Uani 1 1 d . . .
H10 H 0.2587 0.0182 0.5778 0.026 Uiso 1 1 calc R . .
N11 N 0.2777(5) 0.4103(4) 0.1102(3) 0.0131(10) Uani 1 1 d . . .
C12 C 0.4096(7) 0.3730(5) 0.1051(5) 0.0164(13) Uani 1 1 d . . .
N13 N 0.4253(6) 0.3235(4) 0.0047(4) 0.0144(10) Uani 1 1 d . . .
C14 C 0.2975(7) 0.3272(6) -0.0574(5) 0.0188(13) Uani 1 1 d . . .
H14 H 0.2763 0.2975 -0.1314 0.023 Uiso 1 1 calc R . .
C15 C 0.2072(7) 0.3820(6) 0.0080(4) 0.0175(13) Uani 1 1 d . . .
H15 H 0.1110 0.3983 -0.0128 0.021 Uiso 1 1 calc R . .
C16 C 0.5223(7) 0.3825(6) 0.1953(5) 0.0216(13) Uani 1 1 d . . .
H16A H 0.4887 0.4250 0.2599 0.032 Uiso 1 1 calc R . .
H16B H 0.6417 0.4413 0.1913 0.032 Uiso 1 1 calc R . .
H16C H 0.5114 0.2874 0.1945 0.032 Uiso 1 1 calc R . .
C17 C 0.5563(8) 0.2737(6) -0.0313(5) 0.0192(13) Uani 1 1 d . . .
H17A H 0.6704 0.3443 0.0059 0.023 Uiso 1 1 calc R . .
H17B H 0.5571 0.2652 -0.1066 0.023 Uiso 1 1 calc R . .
C18 C 0.5247(7) 0.1311(6) -0.0131(4) 0.0159(12) Uani 1 1 d . . .
C19 C 0.3635(7) 0.0207(5) -0.0409(4) 0.0159(12) Uani 1 1 d . . .
H19 H 0.2695 0.0340 -0.0692 0.019 Uiso 1 1 calc R . .
C20 C 0.3402(7) -0.1104(6) -0.0270(4) 0.0165(13) Uani 1 1 d . . .
H20 H 0.2296 -0.1862 -0.0456 0.020 Uiso 1 1 calc R . .
C21 C -0.1531(10) 0.0638(8) -0.2193(6) 0.045(2) Uani 1 1 d . . .
H21A H -0.1114 0.1562 -0.1653 0.054 Uiso 1 1 calc R . .
H21B H -0.0873 0.0774 -0.2782 0.054 Uiso 1 1 calc R . .
C22 C -0.3389(10) 0.0177(7) -0.2565(6) 0.0386(18) Uani 1 1 d . . .
H22B H -0.3563 0.0971 -0.2733 0.046 Uiso 1 1 calc R . .
H22A H -0.4064 -0.0063 -0.1999 0.046 Uiso 1 1 calc R . .
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'
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'
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
N11 Cu1 N1 136.75(19) . . ?
N11 Cu1 Cl1 99.46(14) . . ?
N1 Cu1 Cl1 103.24(14) . . ?
N11 Cu1 Cl2 99.65(14) . . ?
N1 Cu1 Cl2 98.61(14) . . ?
Cl1 Cu1 Cl2 122.21(7) . . ?
C2 N1 C5 106.3(5) . . ?
C2 N1 Cu1 128.0(4) . . ?
C5 N1 Cu1 125.5(4) . . ?
N1 C2 N3 109.7(5) . . ?
N1 C2 C6 126.1(5) . . ?
N3 C2 C6 124.1(5) . . ?
C2 N3 C4 108.6(5) . . ?
C2 N3 C7 126.1(5) . . ?
C4 N3 C7 125.1(5) . . ?
C5 C4 N3 106.2(5) . . ?
C5 C4 H4 126.9 . . ?
N3 C4 H4 126.9 . . ?
C4 C5 N1 109.1(5) . . ?
C4 C5 H5 125.4 . . ?
N1 C5 H5 125.4 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 C8 110.4(5) . . ?
N3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C10 118.3(5) . 2_556 ?
C9 C8 C7 120.5(5) . . ?
C10 C8 C7 121.2(5) 2_556 . ?
C10 C9 C8 121.2(5) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C8 120.5(6) . 2_556 ?
C9 C10 H10 119.8 . . ?
C8 C10 H10 119.8 2_556 . ?
C12 N11 C15 106.2(5) . . ?
C12 N11 Cu1 123.8(4) . . ?
C15 N11 Cu1 129.8(4) . . ?
N11 C12 N13 110.0(5) . . ?
N11 C12 C16 125.6(5) . . ?
N13 C12 C16 124.4(5) . . ?
C12 N13 C14 108.5(5) . . ?
C12 N13 C17 125.6(5) . . ?
C14 N13 C17 125.9(5) . . ?
C15 C14 N13 106.2(5) . . ?
C15 C14 H14 126.9 . . ?
N13 C14 H14 126.9 . . ?
C14 C15 N11 109.2(5) . . ?
C14 C15 H15 125.4 . . ?
N11 C15 H15 125.4 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N13 C17 C18 112.0(4) . . ?
N13 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N13 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C20 C18 C19 119.9(5) 2_655 . ?
C20 C18 C17 119.3(5) 2_655 . ?
C19 C18 C17 120.8(5) . . ?
C18 C19 C20 119.4(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C18 C20 C19 120.8(5) 2_655 . ?
C18 C20 H20 119.6 2_655 . ?
C19 C20 H20 119.6 . . ?
C22 C21 Cl3 112.4(5) . . ?
C22 C21 H21A 109.1 . . ?
Cl3 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
Cl3 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 Cl4 112.2(5) . . ?
C21 C22 H22B 109.2 . . ?
Cl4 C22 H22B 109.2 . . ?
C21 C22 H22A 109.2 . . ?
Cl4 C22 H22A 109.2 . . ?
H22B C22 H22A 107.9 . . ?
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
Cu1 N11 1.948(5) . ?
Cu1 N1 1.960(5) . ?
Cu1 Cl1 2.249(2) . ?
Cu1 Cl2 2.2571(17) . ?
N1 C2 1.334(7) . ?
N1 C5 1.390(7) . ?
C2 N3 1.343(7) . ?
C2 C6 1.482(7) . ?
Cl3 C21 1.786(8) . ?
N3 C4 1.374(7) . ?
N3 C7 1.477(7) . ?
Cl4 C22 1.771(7) . ?
C4 C5 1.350(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.503(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.384(8) . ?
C8 C10 1.387(8) 2_556 ?
C9 C10 1.376(8) . ?
C9 H9 0.9500 . ?
C10 C8 1.387(8) 2_556 ?
C10 H10 0.9500 . ?
N11 C12 1.330(7) . ?
N11 C15 1.388(7) . ?
C12 N13 1.349(7) . ?
C12 C16 1.477(8) . ?
N13 C14 1.369(7) . ?
N13 C17 1.461(7) . ?
C14 C15 1.358(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.523(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.372(8) 2_655 ?
C18 C19 1.384(7) . ?
C19 C20 1.395(8) . ?
C19 H19 0.9500 . ?
C20 C18 1.372(8) 2_655 ?
C20 H20 0.9500 . ?
C21 C22 1.494(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 Cu1 N1 C2 -67.8(6) . . . . ?
Cl1 Cu1 N1 C2 52.0(5) . . . . ?
Cl2 Cu1 N1 C2 178.1(5) . . . . ?
N11 Cu1 N1 C5 106.0(5) . . . . ?
Cl1 Cu1 N1 C5 -134.2(4) . . . . ?
Cl2 Cu1 N1 C5 -8.1(5) . . . . ?
C5 N1 C2 N3 1.2(6) . . . . ?
Cu1 N1 C2 N3 175.9(4) . . . . ?
C5 N1 C2 C6 -177.1(6) . . . . ?
Cu1 N1 C2 C6 -2.4(8) . . . . ?
N1 C2 N3 C4 -0.5(7) . . . . ?
C6 C2 N3 C4 177.7(5) . . . . ?
N1 C2 N3 C7 -175.4(5) . . . . ?
C6 C2 N3 C7 2.8(9) . . . . ?
C2 N3 C4 C5 -0.3(6) . . . . ?
C7 N3 C4 C5 174.6(5) . . . . ?
N3 C4 C5 N1 1.1(7) . . . . ?
C2 N1 C5 C4 -1.4(6) . . . . ?
Cu1 N1 C5 C4 -176.2(4) . . . . ?
C2 N3 C7 C8 82.7(7) . . . . ?
C4 N3 C7 C8 -91.4(6) . . . . ?
N3 C7 C8 C9 67.4(7) . . . . ?
N3 C7 C8 C10 -113.1(6) . . . 2_556 ?
C10 C8 C9 C10 1.2(10) 2_556 . . . ?
C7 C8 C9 C10 -179.3(6) . . . . ?
C8 C9 C10 C8 -1.2(10) . . . 2_556 ?
N1 Cu1 N11 C12 -55.8(5) . . . . ?
Cl1 Cu1 N11 C12 -176.9(4) . . . . ?
Cl2 Cu1 N11 C12 57.9(4) . . . . ?
N1 Cu1 N11 C15 129.4(5) . . . . ?
Cl1 Cu1 N11 C15 8.3(5) . . . . ?
Cl2 Cu1 N11 C15 -116.9(4) . . . . ?
C15 N11 C12 N13 0.3(6) . . . . ?
Cu1 N11 C12 N13 -175.5(3) . . . . ?
C15 N11 C12 C16 -179.1(5) . . . . ?
Cu1 N11 C12 C16 5.0(7) . . . . ?
N11 C12 N13 C14 -0.8(6) . . . . ?
C16 C12 N13 C14 178.7(5) . . . . ?
N11 C12 N13 C17 179.5(4) . . . . ?
C16 C12 N13 C17 -1.0(8) . . . . ?
C12 N13 C14 C15 0.9(6) . . . . ?
C17 N13 C14 C15 -179.4(5) . . . . ?
N13 C14 C15 N11 -0.7(6) . . . . ?
C12 N11 C15 C14 0.3(6) . . . . ?
Cu1 N11 C15 C14 175.8(4) . . . . ?
C12 N13 C17 C18 72.4(7) . . . . ?
C14 N13 C17 C18 -107.2(6) . . . . ?
N13 C17 C18 C20 -135.5(5) . . . 2_655 ?
N13 C17 C18 C19 47.4(7) . . . . ?
C20 C18 C19 C20 0.4(9) 2_655 . . . ?
C17 C18 C19 C20 177.5(5) . . . . ?
C18 C19 C20 C18 -0.4(9) . . . 2_655 ?
Cl3 C21 C22 Cl4 -68.7(7) . . . . ?
