#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:20:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051933.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_7051933
loop_
_publ_author_name
'Dobrzańska, Liliana'
'Kleinhans, Dewald J.'
'Barbour, Leonard J.'
_publ_section_title
;
 Influence of the metal-to-ligand ratio on the formation of metal
 organic complexes
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              813
_journal_paper_doi               10.1039/b800720a
_journal_volume                  32
_journal_year                    2008
_chemical_formula_moiety         'C28 H28 Cu N10 O6'
_chemical_formula_sum            'C28 H28 Cu N10 O6'
_chemical_formula_weight         664.14
_chemical_name_common            work
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.089(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.336(5)
_cell_length_b                   9.369(4)
_cell_length_c                   13.865(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1434.3(11)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.924
_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  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8758
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.9148
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             686
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0536
_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)+(0.0451P)²+0.8030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                2671
_reflns_number_total             3332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800720a.txt
_cod_data_source_block           V
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7051933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.5000 0.0000 0.0000 0.01116(14) Uani 1 2 d S . .
O21 O 0.47454(19) 0.0721(2) 0.16388(14) 0.0195(5) Uani 1 1 d . . .
N19 N 0.3793(2) 0.1355(3) 0.17368(17) 0.0172(5) Uani 1 1 d . . .
N1 N 0.4499(2) -0.1980(2) 0.02901(17) 0.0127(5) Uani 1 1 d . . .
N14 N -0.1619(2) -0.4142(2) -0.31856(17) 0.0140(5) Uani 1 1 d . . .
N16 N -0.3241(2) -0.4651(2) -0.43454(16) 0.0125(5) Uani 1 1 d . . .
O22 O 0.3687(2) 0.2667(2) 0.15769(15) 0.0243(5) Uani 1 1 d . . .
O20 O 0.2966(2) 0.0675(3) 0.19943(17) 0.0341(6) Uani 1 1 d . . .
N3 N 0.3734(2) -0.4135(2) -0.00233(17) 0.0125(5) Uani 1 1 d . . .
C7 C 0.1876(2) -0.5489(3) -0.0787(2) 0.0128(6) Uani 1 1 d . . .
C12 C 0.1311(3) -0.6581(3) -0.0388(2) 0.0151(6) Uani 1 1 d . . .
H12 H 0.1783 -0.7254 0.0048 0.018 Uiso 1 1 calc R . .
C15 C -0.2819(2) -0.3986(3) -0.3491(2) 0.0130(6) Uani 1 1 d . . .
H15 H -0.3308 -0.3466 -0.3141 0.016 Uiso 1 1 calc R . .
C2 C 0.4129(2) -0.2953(3) -0.0401(2) 0.0131(6) Uani 1 1 d . . .
H2 H 0.4140 -0.2833 -0.1080 0.016 Uiso 1 1 calc R . .
C6 C 0.3244(2) -0.5416(3) -0.0574(2) 0.0146(6) Uani 1 1 d . . .
H6A H 0.3584 -0.6270 -0.0188 0.018 Uiso 1 1 calc R . .
H6B H 0.3505 -0.5437 -0.1208 0.018 Uiso 1 1 calc R . .
C17 C -0.2234(3) -0.5264(3) -0.4590(2) 0.0147(6) Uani 1 1 d . . .
H17 H -0.2248 -0.5819 -0.5165 0.018 Uiso 1 1 calc R . .
C8 C 0.1169(3) -0.4507(3) -0.1418(2) 0.0137(6) Uani 1 1 d . . .
H8 H 0.1551 -0.3761 -0.1698 0.016 Uiso 1 1 calc R . .
C9 C -0.0084(3) -0.4599(3) -0.1644(2) 0.0135(6) Uani 1 1 d . . .
C5 C 0.4336(3) -0.2571(3) 0.1167(2) 0.0143(6) Uani 1 1 d . . .
H5 H 0.4515 -0.2116 0.1796 0.017 Uiso 1 1 calc R . .
C10 C -0.0643(3) -0.5719(3) -0.1253(2) 0.0154(6) Uani 1 1 d . . .
H10 H -0.1500 -0.5807 -0.1419 0.018 Uiso 1 1 calc R . .
C4 C 0.3878(3) -0.3905(3) 0.0981(2) 0.0139(6) Uani 1 1 d . . .
H4 H 0.3692 -0.4556 0.1451 0.017 Uiso 1 1 calc R . .
C13 C -0.0848(3) -0.3494(3) -0.2296(2) 0.0159(6) Uani 1 1 d . . .
H13A H -0.1365 -0.2998 -0.1914 0.019 Uiso 1 1 calc R . .
H13B H -0.0311 -0.2775 -0.2498 0.019 Uiso 1 1 calc R . .
C11 C 0.0052(3) -0.6695(3) -0.0626(2) 0.0172(6) Uani 1 1 d . . .
H11 H -0.0330 -0.7450 -0.0355 0.021 Uiso 1 1 calc R . .
C18 C -0.1225(3) -0.4952(3) -0.3884(2) 0.0165(6) Uani 1 1 d . . .
H18 H -0.0417 -0.5232 -0.3872 0.020 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'
O O 0.0106 0.0060 '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
N1 Cu1 N1 180.00(16) 3_655 . ?
N1 Cu1 N16 93.20(9) 3_655 2_554 ?
N1 Cu1 N16 86.80(9) . 2_554 ?
N1 Cu1 N16 86.80(9) 3_655 4_656 ?
N1 Cu1 N16 93.20(9) . 4_656 ?
N16 Cu1 N16 180.00(15) 2_554 4_656 ?
O22 N19 O20 120.2(3) . . ?
O22 N19 O21 119.6(2) . . ?
O20 N19 O21 120.2(3) . . ?
C2 N1 C5 106.1(2) . . ?
C2 N1 Cu1 123.39(19) . . ?
C5 N1 Cu1 130.18(18) . . ?
C15 N14 C18 107.7(2) . . ?
C15 N14 C13 126.1(2) . . ?
C18 N14 C13 126.1(2) . . ?
C15 N16 C17 105.2(2) . . ?
C15 N16 Cu1 126.57(19) . 2_544 ?
C17 N16 Cu1 127.32(18) . 2_544 ?
C2 N3 C4 106.9(2) . . ?
C2 N3 C6 126.4(2) . . ?
C4 N3 C6 126.7(2) . . ?
C12 C7 C8 119.1(3) . . ?
C12 C7 C6 120.0(3) . . ?
C8 C7 C6 120.8(2) . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N16 C15 N14 111.5(2) . . ?
N16 C15 H15 124.2 . . ?
N14 C15 H15 124.2 . . ?
N1 C2 N3 111.4(2) . . ?
N1 C2 H2 124.3 . . ?
N3 C2 H2 124.3 . . ?
N3 C6 C7 113.0(2) . . ?
N3 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C18 C17 N16 109.9(2) . . ?
C18 C17 H17 125.1 . . ?
N16 C17 H17 125.1 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 C13 120.8(3) . . ?
C10 C9 C13 119.8(3) . . ?
C4 C5 N1 108.9(2) . . ?
C4 C5 H5 125.6 . . ?
N1 C5 H5 125.6 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C5 C4 N3 106.7(2) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
N14 C13 C9 111.7(2) . . ?
N14 C13 H13A 109.3 . . ?
C9 C13 H13A 109.3 . . ?
N14 C13 H13B 109.3 . . ?
C9 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C17 C18 N14 105.7(3) . . ?
C17 C18 H18 127.2 . . ?
N14 C18 H18 127.2 . . ?
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 N1 2.007(2) 3_655 ?
Cu1 N1 2.007(2) . ?
Cu1 N16 2.021(2) 2_554 ?
Cu1 N16 2.021(2) 4_656 ?
O21 N19 1.266(3) . ?
N19 O22 1.250(3) . ?
N19 O20 1.251(3) . ?
N1 C2 1.321(3) . ?
N1 C5 1.386(3) . ?
N14 C15 1.338(4) . ?
N14 C18 1.381(4) . ?
N14 C13 1.472(3) . ?
N16 C15 1.327(3) . ?
N16 C17 1.387(4) . ?
N16 Cu1 2.021(2) 2_544 ?
N3 C2 1.344(3) . ?
N3 C4 1.382(3) . ?
N3 C6 1.463(3) . ?
C7 C12 1.387(4) . ?
C7 C8 1.392(4) . ?
C7 C6 1.513(4) . ?
C12 C11 1.395(4) . ?
C12 H12 0.9500 . ?
C15 H15 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 C18 1.358(4) . ?
C17 H17 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(4) . ?
C9 C13 1.512(4) . ?
C5 C4 1.355(4) . ?
C5 H5 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6b O20 4_544 0.99 2.44 3.323(4) 149
C15 H15 O22 1_555 0.99 2.42 3.274(4) 149
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
N16 Cu1 N1 C2 68.7(2) 2_554 . . . ?
N16 Cu1 N1 C2 -111.3(2) 4_656 . . . ?
N16 Cu1 N1 C5 -103.7(2) 2_554 . . . ?
N16 Cu1 N1 C5 76.3(2) 4_656 . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C6 C7 C12 C11 -176.6(3) . . . . ?
C17 N16 C15 N14 0.0(3) . . . . ?
Cu1 N16 C15 N14 169.57(17) 2_544 . . . ?
C18 N14 C15 N16 0.4(3) . . . . ?
C13 N14 C15 N16 177.0(2) . . . . ?
C5 N1 C2 N3 0.1(3) . . . . ?
Cu1 N1 C2 N3 -173.86(17) . . . . ?
C4 N3 C2 N1 -0.8(3) . . . . ?
C6 N3 C2 N1 179.0(2) . . . . ?
C2 N3 C6 C7 -101.3(3) . . . . ?
C4 N3 C6 C7 78.4(3) . . . . ?
C12 C7 C6 N3 -116.6(3) . . . . ?
C8 C7 C6 N3 66.3(3) . . . . ?
C15 N16 C17 C18 -0.3(3) . . . . ?
Cu1 N16 C17 C18 -169.83(19) 2_544 . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
C6 C7 C8 C9 177.7(2) . . . . ?
C7 C8 C9 C10 -1.8(4) . . . . ?
C7 C8 C9 C13 177.5(2) . . . . ?
C2 N1 C5 C4 0.6(3) . . . . ?
Cu1 N1 C5 C4 174.03(19) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C13 C9 C10 C11 -177.4(2) . . . . ?
N1 C5 C4 N3 -1.1(3) . . . . ?
C2 N3 C4 C5 1.1(3) . . . . ?
C6 N3 C4 C5 -178.7(2) . . . . ?
C15 N14 C13 C9 126.8(3) . . . . ?
C18 N14 C13 C9 -57.1(4) . . . . ?
C8 C9 C13 N14 120.9(3) . . . . ?
C10 C9 C13 N14 -59.9(3) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C7 C12 C11 C10 -0.5(4) . . . . ?
N16 C17 C18 N14 0.5(3) . . . . ?
C15 N14 C18 C17 -0.6(3) . . . . ?
C13 N14 C18 C17 -177.2(2) . . . . ?
