#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:23:52 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/93/7119336.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_7119336
loop_
_publ_author_name
'Yoshida, Takuya'
'Sakamaki, Daisuke'
'Seki, Shu'
'Shinokubo, Hiroshi'
_publ_section_title
;
 Enhancing the low-energy absorption band and charge mobility of
 antiaromatic Ni(II) norcorroles by their substituent effects.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1112
_journal_page_last               1115
_journal_paper_doi               10.1039/c6cc09444a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C16.5 H11 N3 Ni0.5'
_chemical_formula_weight         280.64
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-10-27 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.370(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7913(16)
_cell_length_b                   23.085(4)
_cell_length_c                   9.7956(12)
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      30.8280
_cell_measurement_theta_min      2.7280
_cell_volume                     2414.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7689
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.264
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0902
_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)+(0.1985P)²+2.1688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2609
_refine_ls_wR_factor_ref         0.2814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1647
_reflns_number_total             2129
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc09444a2.cif
_cod_data_source_block           v160430_a
_cod_depositor_comments
'Adding full bibliography for 7119336--7119340.cif.'
_cod_original_formula_sum        'C16.50 H11 N3 Ni0.50'
_cod_database_code               7119336
_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_min   0.571
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.5000 0.3349(3) 0.7500 0.0443(18) Uani 1 2 d S T P
C2 C 0.4195(5) 0.3642(2) 0.6449(5) 0.0457(13) Uani 1 1 d . . .
C3 C 0.3292(5) 0.3457(2) 0.5315(5) 0.0458(13) Uani 1 1 d . . .
H1 H 0.3066 0.3067 0.5094 0.055 Uiso 1 1 calc R U .
C4 C 0.2804(5) 0.3941(2) 0.4595(5) 0.0451(13) Uani 1 1 d . . .
H2 H 0.2198 0.3946 0.3787 0.054 Uiso 1 1 calc R U .
C5 C 0.3393(5) 0.4434(2) 0.5311(5) 0.0448(13) Uani 1 1 d . . .
C6 C 0.3393(5) 0.5074(3) 0.5301(5) 0.0463(13) Uani 1 1 d . . .
C7 C 0.2914(5) 0.5568(2) 0.4500(5) 0.0454(13) Uani 1 1 d . . .
H3 H 0.2362 0.5561 0.3651 0.054 Uiso 1 1 calc R U .
C8 C 0.3410(5) 0.6052(2) 0.5200(5) 0.0442(13) Uani 1 1 d . . .
H4 H 0.3250 0.6442 0.4915 0.053 Uiso 1 1 calc R U .
C9 C 0.4209(5) 0.5872(2) 0.6430(5) 0.0447(13) Uani 1 1 d . . .
C10 C 0.5000 0.6160(4) 0.7500 0.0459(18) Uani 1 2 d S T P
C11 C 0.5000 0.2711(3) 0.7500 0.0435(17) Uani 1 2 d S T P
C12 C 0.5133(5) 0.2393(2) 0.6312(5) 0.0462(13) Uani 1 1 d . . .
H5 H 0.5203 0.2594 0.5481 0.055 Uiso 1 1 calc R U .
C13 C 0.5166(5) 0.1803(2) 0.6316(5) 0.0450(13) Uani 1 1 d . . .
H6 H 0.5304 0.1606 0.5500 0.054 Uiso 1 1 calc R U .
C14 C 0.5000 0.1473(3) 0.7500 0.0406(16) Uani 1 2 d S T P
C15 C 0.5314(6) 0.0570(2) 0.6323(5) 0.0550(15) Uani 1 1 d . . .
H7 H 0.4687 0.0649 0.5516 0.082 Uiso 1 1 calc R U .
H8 H 0.5326 0.0154 0.6526 0.082 Uiso 1 1 calc R U .
H9 H 0.6142 0.0691 0.6131 0.082 Uiso 1 1 calc R U .
C16 C 0.5000 0.6803(4) 0.7500 0.0457(18) Uani 1 2 d S T P
C17 C 0.6126(5) 0.7111(2) 0.7689(5) 0.0452(13) Uani 1 1 d . . .
H10 H 0.6898 0.6907 0.7829 0.054 Uiso 1 1 calc R U .
C18 C 0.6130(5) 0.7706(2) 0.7676(5) 0.0460(13) Uani 1 1 d . . .
H11 H 0.6901 0.7911 0.7786 0.055 Uiso 1 1 calc R U .
C19 C 0.5000 0.8006(3) 0.7500 0.0455(18) Uani 1 2 d S T P
C20 C 0.5000 0.8631(4) 0.7500 0.0492(19) Uani 1 2 d S T P
N1 N 0.4191(4) 0.42341(17) 0.6392(4) 0.0426(11) Uani 1 1 d . . .
N2 N 0.4155(4) 0.52836(17) 0.6419(4) 0.0433(12) Uani 1 1 d . . .
N3 N 0.5000 0.0888(3) 0.7500 0.0466(15) Uani 1 2 d S T P
N4 N 0.5000 0.9124(3) 0.7500 0.0602(18) Uani 1 2 d S T P
Ni1 Ni 0.5000 0.47574(4) 0.7500 0.0451(5) Uani 1 2 d S T P
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'
Ni Ni 0.3393 1.1124 '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
C2 C1 C2 123.0(7) . 2_656
C2 C1 C11 118.5(4) . .
C2 C1 C11 118.5(4) 2_656 .
N1 C2 C1 120.2(5) . .
N1 C2 C3 105.6(5) . .
C1 C2 C3 134.1(5) . .
C4 C3 C2 108.7(5) . .
C4 C3 H1 125.7 . .
C2 C3 H1 125.7 . .
C3 C4 C5 106.3(5) . .
C3 C4 H2 126.8 . .
C5 C4 H2 126.8 . .
N1 C5 C4 107.5(5) . .
N1 C5 C6 110.3(4) . .
C4 C5 C6 142.1(5) . .
N2 C6 C7 106.5(5) . .
N2 C6 C5 110.6(5) . .
C7 C6 C5 142.8(5) . .
C8 C7 C6 106.8(5) . .
C8 C7 H3 126.6 . .
C6 C7 H3 126.6 . .
C7 C8 C9 108.9(5) . .
C7 C8 H4 125.5 . .
C9 C8 H4 125.5 . .
N2 C9 C10 119.6(5) . .
N2 C9 C8 105.2(5) . .
C10 C9 C8 135.1(5) . .
C9 C10 C9 124.1(8) . 2_656
C9 C10 C16 117.9(4) . .
C9 C10 C16 117.9(4) 2_656 .
C12 C11 C12 116.7(7) 2_656 .
C12 C11 C1 121.7(3) 2_656 .
C12 C11 C1 121.7(3) . .
C13 C12 C11 121.9(5) . .
C13 C12 H5 119.0 . .
C11 C12 H5 119.0 . .
C12 C13 C14 122.1(5) . .
C12 C13 H6 118.9 . .
C14 C13 H6 118.9 . .
N3 C14 C13 122.5(3) . .
N3 C14 C13 122.5(3) . 2_656
C13 C14 C13 115.1(7) . 2_656
N3 C15 H7 109.5 . .
N3 C15 H8 109.5 . .
H7 C15 H8 109.5 . .
N3 C15 H9 109.5 . .
H7 C15 H9 109.5 . .
H8 C15 H9 109.5 . .
C17 C16 C17 118.7(7) . 2_656
C17 C16 C10 120.6(4) . .
C17 C16 C10 120.6(4) 2_656 .
C18 C17 C16 120.8(6) . .
C18 C17 H10 119.6 . .
C16 C17 H10 119.6 . .
C17 C18 C19 119.6(5) . .
C17 C18 H11 120.2 . .
C19 C18 H11 120.2 . .
C18 C19 C18 120.3(7) 2_656 .
C18 C19 C20 119.9(3) 2_656 .
C18 C19 C20 119.9(3) . .
N4 C20 C19 180.0 . .
C5 N1 C2 111.8(5) . .
C5 N1 Ni1 116.8(4) . .
C2 N1 Ni1 131.3(4) . .
C6 N2 C9 112.5(5) . .
C6 N2 Ni1 115.8(4) . .
C9 N2 Ni1 131.4(4) . .
C14 N3 C15 120.5(3) . .
C14 N3 C15 120.5(3) . 2_656
C15 N3 C15 119.0(6) . 2_656
N1 Ni1 N1 93.7(3) . 2_656
N1 Ni1 N2 86.4(2) . .
N1 Ni1 N2 178.37(17) 2_656 .
N1 Ni1 N2 178.37(17) . 2_656
N1 Ni1 N2 86.4(2) 2_656 2_656
N2 Ni1 N2 93.6(3) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.419(7) .
C1 C2 1.419(7) 2_656
C1 C11 1.471(11) .
C2 N1 1.368(7) .
C2 C3 1.431(8) .
C3 C4 1.385(8) .
C3 H1 0.9500 .
C4 C5 1.436(8) .
C4 H2 0.9500 .
C5 N1 1.345(7) .
C5 C6 1.477(9) .
C6 N2 1.359(7) .
C6 C7 1.437(8) .
C7 C8 1.379(8) .
C7 H3 0.9500 .
C8 C9 1.437(7) .
C8 H4 0.9500 .
C9 N2 1.360(6) .
C9 C10 1.417(7) .
C10 C9 1.417(7) 2_656
C10 C16 1.485(11) .
C11 C12 1.401(6) 2_656
C11 C12 1.401(6) .
C12 C13 1.362(7) .
C12 H5 0.9500 .
C13 C14 1.421(6) .
C13 H6 0.9500 .
C14 N3 1.349(10) .
C14 C13 1.421(6) 2_656
C15 N3 1.448(6) .
C15 H7 0.9800 .
C15 H8 0.9800 .
C15 H9 0.9800 .
C16 C17 1.397(7) .
C16 C17 1.397(7) 2_656
C17 C18 1.372(7) .
C17 H10 0.9500 .
C18 C19 1.391(7) .
C18 H11 0.9500 .
C19 C18 1.391(7) 2_656
C19 C20 1.444(11) .
C20 N4 1.137(10) .
N1 Ni1 1.767(4) .
N2 Ni1 1.774(4) .
N3 C15 1.448(6) 2_656
Ni1 N1 1.767(4) 2_656
Ni1 N2 1.774(5) 2_656
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_4
C2 C1 C2 N1 1.7(3) 2_656 .
C11 C1 C2 N1 -178.3(3) . .
C2 C1 C2 C3 -178.3(6) 2_656 .
C11 C1 C2 C3 1.7(6) . .
N1 C2 C3 C4 1.6(5) . .
C1 C2 C3 C4 -178.3(4) . .
C2 C3 C4 C5 -1.2(5) . .
C3 C4 C5 N1 0.4(5) . .
C3 C4 C5 C6 -176.6(6) . .
N1 C5 C6 N2 -2.7(5) . .
C4 C5 C6 N2 174.2(6) . .
N1 C5 C6 C7 173.6(6) . .
C4 C5 C6 C7 -9.5(11) . .
N2 C6 C7 C8 -0.7(5) . .
C5 C6 C7 C8 -177.1(6) . .
C6 C7 C8 C9 0.6(5) . .
C7 C8 C9 N2 -0.2(5) . .
C7 C8 C9 C10 176.6(5) . .
N2 C9 C10 C9 2.0(3) . 2_656
C8 C9 C10 C9 -174.4(6) . 2_656
N2 C9 C10 C16 -178.0(3) . .
C8 C9 C10 C16 5.6(6) . .
C2 C1 C11 C12 -129.6(4) . 2_656
C2 C1 C11 C12 50.4(4) 2_656 2_656
C2 C1 C11 C12 50.4(4) . .
C2 C1 C11 C12 -129.6(4) 2_656 .
C12 C11 C12 C13 -1.7(4) 2_656 .
C1 C11 C12 C13 178.3(4) . .
C11 C12 C13 C14 3.4(8) . .
C12 C13 C14 N3 178.3(4) . .
C12 C13 C14 C13 -1.7(4) . 2_656
C9 C10 C16 C17 -132.8(3) . .
C9 C10 C16 C17 47.2(3) 2_656 .
C9 C10 C16 C17 47.2(3) . 2_656
C9 C10 C16 C17 -132.8(3) 2_656 2_656
C17 C16 C17 C18 -0.7(3) 2_656 .
C10 C16 C17 C18 179.3(3) . .
C16 C17 C18 C19 1.3(6) . .
C17 C18 C19 C18 -0.7(3) . 2_656
C17 C18 C19 C20 179.3(3) . .
C4 C5 N1 C2 0.7(5) . .
C6 C5 N1 C2 178.7(4) . .
C4 C5 N1 Ni1 -177.4(3) . .
C6 C5 N1 Ni1 0.6(5) . .
C1 C2 N1 C5 178.5(4) . .
C3 C2 N1 C5 -1.4(6) . .
C1 C2 N1 Ni1 -3.7(7) . .
C3 C2 N1 Ni1 176.3(3) . .
C7 C6 N2 C9 0.6(6) . .
C5 C6 N2 C9 178.3(4) . .
C7 C6 N2 Ni1 -173.9(3) . .
C5 C6 N2 Ni1 3.8(5) . .
C10 C9 N2 C6 -177.6(4) . .
C8 C9 N2 C6 -0.3(6) . .
C10 C9 N2 Ni1 -4.3(7) . .
C8 C9 N2 Ni1 173.1(4) . .
C13 C14 N3 C15 7.1(4) . .
C13 C14 N3 C15 -172.9(4) 2_656 .
C13 C14 N3 C15 -172.9(4) . 2_656
C13 C14 N3 C15 7.1(4) 2_656 2_656
C5 N1 Ni1 N1 179.6(4) . 2_656
C2 N1 Ni1 N1 1.9(4) . 2_656
C5 N1 Ni1 N2 1.2(4) . .
C2 N1 Ni1 N2 -176.5(5) . .
C6 N2 Ni1 N1 -3.0(4) . .
C9 N2 Ni1 N1 -176.1(5) . .
C6 N2 Ni1 N2 175.4(5) . 2_656
C9 N2 Ni1 N2 2.2(4) . 2_656
