#------------------------------------------------------------------------------
#$Date: 2019-11-23 14:02:01 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/90/4349013.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_4349013
loop_
_publ_author_name
'Fanna, Daniel J.'
'Zhang, Yingjie'
'Li, Li'
'Karatchevtseva, Inna'
'Shepherd, Nicholas D.'
'Azim, Abdul'
'Price, Jason R.'
'Aldrich-Wright, Janice'
'Reynolds, Jason K.'
'Li, Feng'
_publ_section_title
;
 3d transition metal complexes with a julolidine--quinoline based ligand:
 structures, spectroscopy and optical properties
;
_journal_issue                   2
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              286
_journal_paper_doi               10.1039/C5QI00200A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C22 H20 N3 Ni0.5 O, H O0.5'
_chemical_formula_sum            'C22 H21 N3 Ni0.5 O1.5'
_chemical_formula_weight         380.77
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-10-09 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.534(4)
_cell_length_b                   13.565(3)
_cell_length_c                   15.695(3)
_cell_measurement_temperature    100(2)
_cell_volume                     3552.4(18)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BlueIce (McPhillips, et al., 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ADSC Quantum Detector'
_diffrn_measurement_method       'π  scans'
_diffrn_radiation_type
'silicon double crystal monochromated synchrotron'
_diffrn_radiation_wavelength     0.71074
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59558
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'Australian Synchrotron MX1'
_exptl_absorpt_coefficient_mu    0.599
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+5.3363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3877
_reflns_number_total             4254
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5qi00200a2.cif
_cod_data_source_block           c2_a
_cod_original_cell_volume        3552.3(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C22 H21 N3 Ni0.50 O1.50'
_cod_database_code               4349013
_shelxl_version_number           2014-3
_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, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Ni1 Ni 0.5000 0.59222(2) 0.7500 0.01444(8) Uani 1 2 d S T P
O1 O 0.58700(6) 0.49057(8) 0.83697(8) 0.0183(2) Uani 1 1 d . . .
N1 N 0.42129(8) 0.70308(9) 0.64963(10) 0.0184(3) Uani 1 1 d . . .
N2 N 0.52764(8) 0.59575(9) 0.64573(10) 0.0168(2) Uani 1 1 d . . .
N3 N 0.85659(8) 0.38022(11) 1.02681(11) 0.0251(3) Uani 1 1 d . . .
C1 C 0.37617(10) 0.76295(12) 0.66059(13) 0.0227(3) Uani 1 1 d . . .
H1 H 0.3796 0.7597 0.7223 0.027 Uiso 1 1 calc R . .
C2 C 0.32299(10) 0.83162(13) 0.58350(14) 0.0262(3) Uani 1 1 d . . .
H2 H 0.2940 0.8748 0.5955 0.031 Uiso 1 1 calc R . .
C3 C 0.31492(10) 0.83347(12) 0.49066(13) 0.0253(3) Uani 1 1 d . . .
H3 H 0.2787 0.8766 0.4377 0.030 Uiso 1 1 calc R . .
C4 C 0.36170(9) 0.76980(12) 0.47538(12) 0.0216(3) Uani 1 1 d . . .
C5 C 0.35691(10) 0.76619(13) 0.38168(13) 0.0259(3) Uani 1 1 d . . .
H5 H 0.3202 0.8057 0.3250 0.031 Uiso 1 1 calc R . .
C6 C 0.40629(10) 0.70457(12) 0.37434(12) 0.0249(3) Uani 1 1 d . . .
H6 H 0.4016 0.7014 0.3118 0.030 Uiso 1 1 calc R . .
C7 C 0.46426(10) 0.64565(12) 0.46014(12) 0.0210(3) Uani 1 1 d . . .
H7 H 0.4980 0.6055 0.4539 0.025 Uiso 1 1 calc R . .
C8 C 0.47111(9) 0.64722(11) 0.55298(11) 0.0179(3) Uani 1 1 d . . .
C9 C 0.41682(9) 0.70717(11) 0.55943(12) 0.0184(3) Uani 1 1 d . . .
C10 C 0.59532(9) 0.56519(11) 0.66530(11) 0.0177(3) Uani 1 1 d . . .
H10 H 0.6043 0.5778 0.6146 0.021 Uiso 1 1 calc R . .
C11 C 0.65668(9) 0.51437(11) 0.75694(11) 0.0171(3) Uani 1 1 d . . .
C12 C 0.72878(9) 0.49510(11) 0.76731(12) 0.0194(3) Uani 1 1 d . . .
H12 H 0.7315 0.5133 0.7123 0.023 Uiso 1 1 calc R . .
C13 C 0.79459(9) 0.45153(12) 0.85298(12) 0.0208(3) Uani 1 1 d . . .
C14 C 0.87154(11) 0.44058(14) 0.86206(15) 0.0293(4) Uani 1 1 d . . .
H14A H 0.9000 0.5030 0.8834 0.035 Uiso 1 1 calc R . .
H14B H 0.8593 0.4232 0.7942 0.035 Uiso 1 1 calc R . .
C15 C 0.92448(11) 0.36173(16) 0.94141(16) 0.0345(4) Uani 1 1 d . . .
H15A H 0.9005 0.2974 0.9144 0.041 Uiso 1 1 calc R . .
H15B H 0.9766 0.3622 0.9537 0.041 Uiso 1 1 calc R . .
C16 C 0.93412(11) 0.38108(16) 1.04313(16) 0.0349(4) Uani 1 1 d . . .
H16A H 0.9684 0.3310 1.0941 0.042 Uiso 1 1 calc R . .
H16B H 0.9596 0.4446 1.0709 0.042 Uiso 1 1 calc R . .
C17 C 0.86087(11) 0.38309(14) 1.12309(14) 0.0303(4) Uani 1 1 d . . .
H17A H 0.8708 0.4501 1.1493 0.036 Uiso 1 1 calc R . .
H17B H 0.9050 0.3423 1.1761 0.036 Uiso 1 1 calc R . .
C18 C 0.78360(11) 0.34637(14) 1.10264(13) 0.0294(4) Uani 1 1 d . . .
H18A H 0.7864 0.3522 1.1663 0.035 Uiso 1 1 calc R . .
H18B H 0.7768 0.2772 1.0837 0.035 Uiso 1 1 calc R . .
C19 C 0.71133(10) 0.40402(13) 1.01504(13) 0.0241(3) Uani 1 1 d . . .
H19A H 0.6637 0.3637 0.9851 0.029 Uiso 1 1 calc R . .
H19B H 0.7044 0.4625 1.0446 0.029 Uiso 1 1 calc R . .
C20 C 0.79028(9) 0.42204(11) 0.93727(12) 0.0197(3) Uani 1 1 d . . .
C21 C 0.71895(9) 0.43478(11) 0.92870(12) 0.0183(3) Uani 1 1 d . . .
C22 C 0.65099(9) 0.48116(11) 0.83953(11) 0.0161(3) Uani 1 1 d . . .
O1W O 0.5000 0.31397(14) 0.7500 0.0356(4) Uani 1 2 d S T P
H1W H 0.4621(17) 0.354(2) 0.702(2) 0.070(9) Uiso 1 1 d . . .
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'
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
O1 Ni1 O1 94.32(7) 2_656 .
O1 Ni1 N1 170.12(5) . .
O1 Ni1 N1 89.49(6) . 2_656
O1 Ni1 N1 89.49(6) 2_656 .
O1 Ni1 N1 170.12(5) 2_656 2_656
N1 Ni1 N1 88.23(8) . 2_656
N2 Ni1 O1 91.37(5) . 2_656
N2 Ni1 O1 90.47(5) . .
N2 Ni1 O1 91.37(5) 2_656 .
N2 Ni1 O1 90.47(5) 2_656 2_656
N2 Ni1 N1 80.32(5) 2_656 2_656
N2 Ni1 N1 97.71(5) 2_656 .
N2 Ni1 N1 80.32(5) . .
N2 Ni1 N1 97.71(5) . 2_656
N2 Ni1 N2 177.29(7) . 2_656
C22 O1 Ni1 124.51(10) . .
C1 N1 Ni1 129.64(11) . .
C1 N1 C9 118.90(14) . .
C9 N1 Ni1 111.41(10) . .
C8 N2 Ni1 113.41(10) . .
C10 N2 Ni1 124.44(11) . .
C10 N2 C8 121.61(13) . .
C16 N3 C17 114.62(15) . .
C20 N3 C16 120.12(15) . .
C20 N3 C17 117.96(14) . .
N1 C1 H1 118.4 . .
N1 C1 C2 123.23(15) . .
C2 C1 H1 118.4 . .
C1 C2 H2 120.7 . .
C3 C2 C1 118.64(16) . .
C3 C2 H2 120.7 . .
C2 C3 H3 120.1 . .
C2 C3 C4 119.85(15) . .
C4 C3 H3 120.1 . .
C3 C4 C5 123.71(15) . .
C3 C4 C9 117.55(15) . .
C9 C4 C5 118.74(15) . .
C4 C5 H5 119.9 . .
C6 C5 C4 120.11(15) . .
C6 C5 H5 119.9 . .
C5 C6 H6 119.4 . .
C5 C6 C7 121.21(15) . .
C7 C6 H6 119.4 . .
C6 C7 H7 119.7 . .
C8 C7 C6 120.52(16) . .
C8 C7 H7 119.7 . .
N2 C8 C9 114.55(13) . .
C7 C8 N2 126.80(15) . .
C7 C8 C9 118.65(14) . .
N1 C9 C4 121.65(14) . .
N1 C9 C8 117.79(13) . .
C4 C9 C8 120.55(14) . .
N2 C10 H10 117.0 . .
N2 C10 C11 125.95(14) . .
C11 C10 H10 117.0 . .
C10 C11 C22 125.01(14) . .
C12 C11 C10 117.16(14) . .
C12 C11 C22 117.83(14) . .
C11 C12 H12 117.9 . .
C13 C12 C11 124.13(14) . .
C13 C12 H12 117.9 . .
C12 C13 C14 121.09(15) . .
C12 C13 C20 118.14(14) . .
C20 C13 C14 120.66(15) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 C15 110.92(15) . .
H14A C14 H14B 108.0 . .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
C14 C15 H15A 109.8 . .
C14 C15 H15B 109.8 . .
H15A C15 H15B 108.2 . .
C16 C15 C14 109.55(16) . .
C16 C15 H15A 109.8 . .
C16 C15 H15B 109.8 . .
N3 C16 C15 110.82(16) . .
N3 C16 H16A 109.5 . .
N3 C16 H16B 109.5 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 108.1 . .
N3 C17 H17A 109.6 . .
N3 C17 H17B 109.6 . .
N3 C17 C18 110.44(15) . .
H17A C17 H17B 108.1 . .
C18 C17 H17A 109.6 . .
C18 C17 H17B 109.6 . .
C17 C18 H18A 109.2 . .
C17 C18 H18B 109.2 . .
C17 C18 C19 111.88(15) . .
H18A C18 H18B 107.9 . .
C19 C18 H18A 109.2 . .
C19 C18 H18B 109.2 . .
C18 C19 H19A 108.9 . .
C18 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C21 C19 C18 113.28(14) . .
C21 C19 H19A 108.9 . .
C21 C19 H19B 108.9 . .
N3 C20 C13 119.84(14) . .
N3 C20 C21 120.13(14) . .
C21 C20 C13 120.02(14) . .
C20 C21 C19 121.93(14) . .
C20 C21 C22 121.32(14) . .
C22 C21 C19 116.71(14) . .
O1 C22 C11 123.61(13) . .
O1 C22 C21 117.96(13) . .
C21 C22 C11 118.43(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0281(12) 2_656
Ni1 O1 2.0281(12) .
Ni1 N1 2.0945(14) .
Ni1 N1 2.0945(14) 2_656
Ni1 N2 2.0213(13) .
Ni1 N2 2.0214(13) 2_656
O1 C22 1.2973(18) .
N1 C1 1.317(2) .
N1 C9 1.365(2) .
N2 C8 1.4086(19) .
N2 C10 1.304(2) .
N3 C16 1.458(2) .
N3 C17 1.462(2) .
N3 C20 1.386(2) .
C1 H1 0.9300 .
C1 C2 1.408(2) .
C2 H2 0.9300 .
C2 C3 1.367(3) .
C3 H3 0.9300 .
C3 C4 1.412(2) .
C4 C5 1.416(2) .
C4 C9 1.415(2) .
C5 H5 0.9300 .
C5 C6 1.370(3) .
C6 H6 0.9300 .
C6 C7 1.414(2) .
C7 H7 0.9300 .
C7 C8 1.380(2) .
C8 C9 1.430(2) .
C10 H10 0.9300 .
C10 C11 1.421(2) .
C11 C12 1.416(2) .
C11 C22 1.440(2) .
C12 H12 0.9300 .
C12 C13 1.366(2) .
C13 C14 1.509(2) .
C13 C20 1.433(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.516(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.513(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.508(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 C19 1.525(2) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 C21 1.511(2) .
C20 C21 1.401(2) .
C21 C22 1.423(2) .
O1W H1W 0.89(3) .
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
Ni1 O1 C22 C11 -23.3(2)
Ni1 O1 C22 C21 157.21(11)
Ni1 N1 C1 C2 -177.05(12)
Ni1 N1 C9 C4 173.80(11)
Ni1 N1 C9 C8 -7.44(17)
Ni1 N2 C8 C7 -165.87(13)
Ni1 N2 C8 C9 14.78(16)
Ni1 N2 C10 C11 7.8(2)
N1 C1 C2 C3 3.0(3)
N2 C8 C9 N1 -4.6(2)
N2 C8 C9 C4 174.21(13)
N2 C10 C11 C12 -174.60(14)
N2 C10 C11 C22 5.4(2)
N3 C17 C18 C19 -55.8(2)
N3 C20 C21 C19 0.0(2)
N3 C20 C21 C22 177.40(14)
C1 N1 C9 C4 -3.8(2)
C1 N1 C9 C8 174.97(14)
C1 C2 C3 C4 -2.3(3)
C2 C3 C4 C5 179.53(16)
C2 C3 C4 C9 -1.1(2)
C3 C4 C5 C6 177.86(16)
C3 C4 C9 N1 4.3(2)
C3 C4 C9 C8 -174.40(14)
C4 C5 C6 C7 -1.8(3)
C5 C4 C9 N1 -176.31(14)
C5 C4 C9 C8 5.0(2)
C5 C6 C7 C8 1.5(2)
C6 C7 C8 N2 -177.39(14)
C6 C7 C8 C9 1.9(2)
C7 C8 C9 N1 176.03(14)
C7 C8 C9 C4 -5.2(2)
C8 N2 C10 C11 178.85(14)
C9 N1 C1 C2 0.0(2)
C9 C4 C5 C6 -1.5(2)
C10 N2 C8 C7 22.2(2)
C10 N2 C8 C9 -157.18(14)
C10 C11 C12 C13 176.58(15)
C10 C11 C22 O1 3.1(2)
C10 C11 C22 C21 -177.41(14)
C11 C12 C13 C14 -175.16(15)
C11 C12 C13 C20 0.9(2)
C12 C11 C22 O1 -176.90(14)
C12 C11 C22 C21 2.6(2)
C12 C13 C14 C15 -160.48(16)
C12 C13 C20 N3 -178.12(15)
C12 C13 C20 C21 2.4(2)
C13 C14 C15 C16 -51.2(2)
C13 C20 C21 C19 179.45(15)
C13 C20 C21 C22 -3.1(2)
C14 C13 C20 N3 -2.0(2)
C14 C13 C20 C21 178.50(15)
C14 C15 C16 N3 59.7(2)
C16 N3 C17 C18 -159.95(16)
C16 N3 C20 C13 10.2(2)
C16 N3 C20 C21 -170.29(16)
C17 N3 C16 C15 171.01(16)
C17 N3 C20 C13 158.80(15)
C17 N3 C20 C21 -21.7(2)
C17 C18 C19 C21 35.5(2)
C18 C19 C21 C20 -7.9(2)
C18 C19 C21 C22 174.53(14)
C19 C21 C22 O1 -2.3(2)
C19 C21 C22 C11 178.10(14)
C20 N3 C16 C15 -39.4(2)
C20 N3 C17 C18 49.8(2)
C20 C13 C14 C15 23.5(2)
C20 C21 C22 O1 -179.91(14)
C20 C21 C22 C11 0.5(2)
C22 C11 C12 C13 -3.5(2)
