#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:44:19 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179260 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/80/4318054.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_4318054
loop_
_publ_author_name
'Paul V. Bernhardt'
'Evan G. Moore'
'Mark J. Riley'
_publ_section_title
;
 Intramolecular Electronic Energy Transfer in Bichromophoric Macrocyclic
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3025
_journal_page_last               3031
_journal_paper_doi               10.1021/ic0255306
_journal_volume                  41
_journal_year                    2002
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C44 H50 Cl2 N6 Ni1 O8'
_chemical_formula_structural     'C44 H50 NI N6 CL2 O8'
_chemical_formula_sum            'C38 H52 Cl2 N8 Ni O8'
_chemical_formula_weight         878.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2002-01-17T11:17:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.735(2)
_cell_length_b                   8.2791(7)
_cell_length_c                   20.136(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_measurement_wavelength     0.71073
_cell_volume                     2052.5(4)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.11787E-1
_diffrn_orient_matrix_UB_12      -0.31617E-1
_diffrn_orient_matrix_UB_13      -0.45464E-1
_diffrn_orient_matrix_UB_21      -0.79798E-1
_diffrn_orient_matrix_UB_22      -0.18447E-1
_diffrn_orient_matrix_UB_23      -0.18247E-1
_diffrn_orient_matrix_UB_31      -0.9529E-2
_diffrn_orient_matrix_UB_32      0.115134
_diffrn_orient_matrix_UB_33      -0.15434E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1903
_diffrn_reflns_av_unetI/netI     0.199
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3756
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.72
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        21
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.664
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.755
_refine_diff_density_min         -1.466
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.2782
_refine_ls_R_factor_gt           0.1078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2871
_refine_ls_wR_factor_ref         0.3834
_reflns_number_gt                1217
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0255306_s1_1.cif
_cod_data_source_block           1793em18
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4318054
#BEGIN Tags that were not found in dictionaries:
_diffrn_standards_decay_corr_max 1.256
_diffrn_standards_decay_corr_min 0.969
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Ni1 Ni 0.5 1 0.5 0.0661(10) Uani 1 2 d S . .
N1 N 0.5949(6) 0.8101(11) 0.5186(4) 0.027(2) Uani 1 1 d . . .
H1 H 0.5514 0.7239 0.5205 0.033 Uiso 1 1 calc R . .
N2 N 0.5090(6) 1.0221(11) 0.5967(4) 0.028(2) Uani 1 1 d . . .
H2 H 0.4627 0.9477 0.6066 0.034 Uiso 1 1 calc R . .
N3 N 0.5751(7) 0.7151(11) 0.6545(5) 0.034(2) Uani 1 1 d . . .
H3 H 0.5887 0.6239 0.6501 0.041 Uiso 1 1 d R . .
N4 N 0.4879(12) 0.090(2) 0.7839(9) 0.092(5) Uani 1 1 d . . .
C1 C 0.6306(9) 0.7916(15) 0.4568(6) 0.039(3) Uani 1 1 d . . .
H1A H 0.6617 0.6848 0.456 0.046 Uiso 1 1 calc R . .
H1B H 0.6868 0.8705 0.4564 0.046 Uiso 1 1 calc R . .
C2 C 0.6884(9) 0.8001(13) 0.5807(6) 0.034(3) Uani 1 1 d . . .
H2A H 0.7428 0.8782 0.5761 0.04 Uiso 1 1 calc R . .
H2B H 0.7207 0.6936 0.5823 0.04 Uiso 1 1 calc R . .
C3 C 0.6593(8) 0.8307(15) 0.6488(5) 0.035(3) Uani 1 1 d . . .
C4 C 0.6142(8) 1.0014(14) 0.6495(5) 0.029(3) Uani 1 1 d . . .
H4A1 H 0.6034 1.024 0.6946 0.034 Uiso 1 1 calc R . .
H4A2 H 0.6665 1.0785 0.6409 0.034 Uiso 1 1 calc R . .
C5 C 0.4622(10) 1.1861(13) 0.6063(6) 0.037(3) Uani 1 1 d . . .
H5A1 H 0.4364 1.1881 0.6477 0.044 Uiso 1 1 calc R . .
H5A2 H 0.5162 1.2703 0.6094 0.044 Uiso 1 1 calc R . .
C6 C 0.7662(9) 0.8187(17) 0.7053(6) 0.046(3) Uani 1 1 d . . .
H6A1 H 0.7546 0.8547 0.7481 0.07 Uiso 1 1 calc R . .
H6A2 H 0.8203 0.8852 0.6933 0.07 Uiso 1 1 calc R . .
H6A3 H 0.7905 0.7085 0.7097 0.07 Uiso 1 1 calc R . .
C7 C 0.5559(9) 0.7059(14) 0.7223(5) 0.036(3) Uani 1 1 d . . .
H7A H 0.5489 0.8148 0.7384 0.043 Uiso 1 1 calc R . .
H7B H 0.619 0.6574 0.7534 0.043 Uiso 1 1 calc R . .
C8 C 0.4564(9) 0.6108(14) 0.7261(6) 0.034(3) Uani 1 1 d . . .
C9 C 0.4331(9) 0.5852(15) 0.7909(6) 0.038(3) Uani 1 1 d . . .
C10 C 0.3395(10) 0.4942(17) 0.7954(7) 0.045(3) Uani 1 1 d . . .
C11 C 0.2742(11) 0.4312(17) 0.7335(9) 0.059(4) Uani 1 1 d . . .
H11 H 0.2145 0.3681 0.7352 0.071 Uiso 1 1 calc R . .
C12 C 0.2948(10) 0.4587(19) 0.6720(8) 0.062(4) Uani 1 1 d . . .
H12 H 0.2482 0.4169 0.6324 0.075 Uiso 1 1 calc R . .
C13 C 0.3853(9) 0.5494(15) 0.6669(6) 0.041(3) Uani 1 1 d . . .
H13 H 0.3979 0.5687 0.6242 0.05 Uiso 1 1 calc R . .
C14 C 0.3178(12) 0.474(2) 0.8587(9) 0.072(5) Uani 1 1 d . . .
H14 H 0.2565 0.4163 0.8614 0.086 Uiso 1 1 calc R . .
C15 C 0.3826(15) 0.536(3) 0.9166(8) 0.084(6) Uani 1 1 d . . .
H15 H 0.3665 0.5193 0.9586 0.1 Uiso 1 1 calc R . .
C16 C 0.4725(15) 0.623(3) 0.9134(8) 0.086(6) Uani 1 1 d . . .
H16 H 0.5169 0.6663 0.9535 0.103 Uiso 1 1 calc R . .
C17 C 0.4982(11) 0.6483(19) 0.8519(7) 0.057(4) Uani 1 1 d . . .
H17 H 0.5597 0.708 0.8509 0.068 Uiso 1 1 calc R . .
C18 C 0.4903(12) 0.103(2) 0.8386(10) 0.067(5) Uani 1 1 d . . .
C19 C 0.4925(13) 0.125(3) 0.9066(9) 0.093(6) Uani 1 1 d . . .
H19A H 0.4217 0.1572 0.9102 0.139 Uiso 1 1 calc R . .
H19B H 0.5441 0.2084 0.9256 0.139 Uiso 1 1 calc R . .
H19C H 0.5133 0.0266 0.9314 0.139 Uiso 1 1 calc R . .
Cl1 Cl 0.7115(2) 1.3396(4) 0.53343(16) 0.0407(9) Uani 1 1 d D . .
O1 O 0.6089(12) 1.427(2) 0.5210(18) 0.043(7) Uiso 0.58(10) 1 d PD A 1
O2 O 0.7812(18) 1.407(3) 0.4949(16) 0.059(8) Uiso 0.58(10) 1 d PD A 1
O3 O 0.761(3) 1.340(3) 0.6047(8) 0.063(7) Uiso 0.58(10) 1 d PD A 1
O4 O 0.685(3) 1.1763(18) 0.5107(14) 0.082(12) Uiso 0.58(10) 1 d PD A 1
O1A O 0.7924(18) 1.427(3) 0.512(2) 0.052(11) Uiso 0.42(10) 1 d PD A 2
O2A O 0.6066(12) 1.417(3) 0.503(2) 0.032(9) Uiso 0.42(10) 1 d PD A 2
O3A O 0.707(3) 1.1765(18) 0.5191(16) 0.053(12) Uiso 0.42(10) 1 d PD A 2
O4A O 0.734(4) 1.363(4) 0.6083(7) 0.051(10) Uiso 0.42(10) 1 d PD 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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-7 0 1
-1 -1 -10
-1 5 0
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
N2 Ni1 N2 180.000(2) . 3_676 ?
N2 Ni1 N1 90.5(4) . . ?
N2 Ni1 N1 89.5(4) 3_676 . ?
N2 Ni1 N1 89.5(4) . 3_676 ?
N2 Ni1 N1 90.5(4) 3_676 3_676 ?
N1 Ni1 N1 180.000(3) . 3_676 ?
C1 N1 C2 111.0(8) . . ?
C1 N1 Ni1 103.7(7) . . ?
C2 N1 Ni1 121.7(7) . . ?
C4 N2 C5 108.8(8) . . ?
C4 N2 Ni1 121.3(6) . . ?
C5 N2 Ni1 106.9(6) . . ?
C7 N3 C3 114.3(8) . . ?
N1 C1 C5 111.3(9) . 3_676 ?
N1 C2 C3 114.7(9) . . ?
N3 C3 C4 108.6(9) . . ?
N3 C3 C2 108.1(9) . . ?
C4 C3 C2 109.8(9) . . ?
N3 C3 C6 115.4(9) . . ?
C4 C3 C6 108.5(9) . . ?
C2 C3 C6 106.3(10) . . ?
N2 C4 C3 111.8(8) . . ?
C1 C5 N2 104.5(9) 3_676 . ?
N3 C7 C8 114.8(9) . . ?
C13 C8 C9 119.1(11) . . ?
C13 C8 C7 121.2(10) . . ?
C9 C8 C7 119.7(10) . . ?
C17 C9 C8 122.3(12) . . ?
C17 C9 C10 117.3(12) . . ?
C8 C9 C10 120.4(11) . . ?
C14 C10 C11 124.0(14) . . ?
C14 C10 C9 119.1(13) . . ?
C11 C10 C9 116.9(12) . . ?
C12 C11 C10 122.7(13) . . ?
C11 C12 C13 120.9(13) . . ?
C8 C13 C12 120.0(12) . . ?
C15 C14 C10 122.1(15) . . ?
C14 C15 C16 119.7(15) . . ?
C15 C16 C17 121.0(16) . . ?
C16 C17 C9 120.8(15) . . ?
N4 C18 C19 178(2) . . ?
O3A Cl1 O3 101.4(16) . . ?
O3A Cl1 O1A 115.6(13) . . ?
O3 Cl1 O1A 98.0(15) . . ?
O3A Cl1 O2 105.5(17) . . ?
O3 Cl1 O2 111.7(10) . . ?
O1A Cl1 O2 14.9(15) . . ?
O3A Cl1 O4 11.1(18) . . ?
O3 Cl1 O4 109.3(11) . . ?
O1A Cl1 O4 120.5(18) . . ?
O2 Cl1 O4 108.4(12) . . ?
O3A Cl1 O1 117.3(16) . . ?
O3 Cl1 O1 109.0(10) . . ?
O1A Cl1 O1 112.6(15) . . ?
O2 Cl1 O1 111.6(10) . . ?
O4 Cl1 O1 106.7(11) . . ?
O3A Cl1 O2A 110.9(13) . . ?
O3 Cl1 O2A 123.1(12) . . ?
O1A Cl1 O2A 107.7(11) . . ?
O2 Cl1 O2A 103.3(14) . . ?
O4 Cl1 O2A 99.8(15) . . ?
O1 Cl1 O2A 14.1(12) . . ?
O3A Cl1 O4A 109.3(12) . . ?
O3 Cl1 O4A 16.8(13) . . ?
O1A Cl1 O4A 106.5(12) . . ?
O2 Cl1 O4A 121.3(14) . . ?
O4 Cl1 O4A 114.8(16) . . ?
O1 Cl1 O4A 92.2(13) . . ?
O2A Cl1 O4A 106.3(11) . . ?
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
Ni1 N2 1.930(8) . ?
Ni1 N2 1.930(8) 3_676 ?
Ni1 N1 1.960(9) . ?
Ni1 N1 1.960(9) 3_676 ?
N1 C1 1.438(14) . ?
N1 C2 1.493(14) . ?
N2 C4 1.492(12) . ?
N2 C5 1.515(14) . ?
N3 C7 1.450(14) . ?
N3 C3 1.463(14) . ?
N4 C18 1.10(2) . ?
C1 C5 1.510(16) 3_676 ?
C2 C3 1.530(16) . ?
C3 C4 1.527(16) . ?
C3 C6 1.537(14) . ?
C5 C1 1.510(16) 3_676 ?
C7 C8 1.510(16) . ?
C8 C13 1.395(16) . ?
C8 C9 1.427(16) . ?
C9 C17 1.395(17) . ?
C9 C10 1.433(17) . ?
C10 C14 1.383(19) . ?
C10 C11 1.408(19) . ?
C11 C12 1.350(19) . ?
C12 C13 1.401(18) . ?
C14 C15 1.34(2) . ?
C15 C16 1.37(2) . ?
C16 C17 1.376(19) . ?
C18 C19 1.38(2) . ?
Cl1 O3A 1.379(15) . ?
Cl1 O3 1.414(12) . ?
Cl1 O1A 1.419(14) . ?
Cl1 O2 1.433(12) . ?
Cl1 O4 1.439(14) . ?
Cl1 O1 1.457(12) . ?
Cl1 O2A 1.467(13) . ?
Cl1 O4A 1.474(15) . ?
