#------------------------------------------------------------------------------
#$Date: 2022-03-11 00:56:44 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273614 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129798.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_7129798
loop_
_publ_author_name
'Adhikari, Sanjay'
'Sarkar, Aniruddha'
'Dhar, Basab Bijayi'
_publ_section_title
;
 C--H bond chlorination using nickel(ii) complexes of tetradentate
 amido-quinoline ligands
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00639A
_journal_year                    2022
_chemical_formula_moiety         'C23 H18 N4 Ni O2'
_chemical_formula_sum            'C23 H18 N4 Ni O2'
_chemical_formula_weight         441.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-07 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.232(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.456(3)
_cell_length_b                   14.261(3)
_cell_length_c                   13.237(3)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.80
_cell_volume                     1953.5(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29713
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_min         2.432
_exptl_absorpt_coefficient_mu    1.022
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       Block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0319
_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)+(0.0300P)²+0.8744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3965
_reflns_number_total             5029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00639a2.cif
_cod_data_source_block           sa-1
_cod_database_code               7129798
_shelx_shelxl_version_number     2016/4
_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_max   0.941
_shelx_estimated_absorpt_t_min   0.799
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C13(H13), C22(H22), C15(H15), C7(H7), C16(H16), C20(H20),
 C12(H12), C9(H9), C8(H8), C21(H21)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.41402(2) 0.34207(2) 0.63662(2) 0.03423(8) Uani 1 1 d . . . . .
N4 N 0.42799(14) 0.47505(10) 0.61792(11) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.42362(13) 0.21156(10) 0.61909(12) 0.0368(3) Uani 1 1 d . . . . .
N3 N 0.25614(14) 0.35313(10) 0.54940(12) 0.0382(3) Uani 1 1 d . . . . .
N2 N 0.56633(14) 0.32373(11) 0.73278(12) 0.0379(3) Uani 1 1 d . . . . .
O1 O 0.34215(16) 0.06770(11) 0.57001(17) 0.0736(5) Uani 1 1 d . . . . .
O2 O 0.09016(16) 0.28568(12) 0.44414(14) 0.0718(5) Uani 1 1 d . . . . .
C18 C 0.75349(18) 0.21996(14) 0.75871(16) 0.0439(4) Uani 1 1 d . . . . .
C19 C 0.62690(17) 0.24187(13) 0.71225(14) 0.0368(4) Uani 1 1 d . . . . .
C11 C 0.32625(18) 0.51001(13) 0.55084(14) 0.0379(4) Uani 1 1 d . . . . .
C23 C 0.55194(17) 0.17991(13) 0.64451(14) 0.0365(4) Uani 1 1 d . . . . .
C6 C 0.23193(18) 0.44395(13) 0.51005(15) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.32712(19) 0.15108(13) 0.58859(17) 0.0444(5) Uani 1 1 d . . . . .
C5 C 0.17510(17) 0.28139(14) 0.51784(16) 0.0433(4) Uani 1 1 d . . . . .
C2 C 0.18973(18) 0.19165(14) 0.58264(17) 0.0468(5) Uani 1 1 d . . . . .
C17 C 0.8130(2) 0.28233(17) 0.83330(17) 0.0541(6) Uani 1 1 d . . . . .
H17 H 0.897397 0.271801 0.864276 0.065 Uiso 1 1 calc R . . . .
C14 C 0.5259(2) 0.53240(13) 0.64875(15) 0.0440(4) Uani 1 1 d . . . . .
H14 H 0.597129 0.508572 0.691126 0.053 Uiso 1 1 calc R . . . .
C10 C 0.3201(2) 0.60517(13) 0.52085(16) 0.0452(5) Uani 1 1 d . . . . .
C13 C 0.5271(2) 0.62697(14) 0.62055(16) 0.0493(5) Uani 1 1 d . . . . .
H13 H 0.597683 0.664649 0.644181 0.059 Uiso 1 1 calc R . . . .
C22 C 0.6096(2) 0.09878(14) 0.61642(17) 0.0472(5) Uani 1 1 d . . . . .
H22 H 0.563974 0.057432 0.570282 0.057 Uiso 1 1 calc R . . . .
C15 C 0.6229(2) 0.37733(15) 0.80785(16) 0.0458(5) Uani 1 1 d . . . . .
H15 H 0.578952 0.429708 0.826756 0.055 Uiso 1 1 calc R . . . .
C7 C 0.1302(2) 0.47614(16) 0.44027(17) 0.0535(5) Uani 1 1 d . . . . .
H7 H 0.067297 0.434505 0.410742 0.064 Uiso 1 1 calc R . . . .
C16 C 0.7462(2) 0.35825(16) 0.85980(18) 0.0546(6) Uani 1 1 d . . . . .
H16 H 0.782555 0.397381 0.912408 0.065 Uiso 1 1 calc R . . . .
C20 C 0.8086(2) 0.13592(17) 0.72878(19) 0.0558(6) Uani 1 1 d . . . . .
H20 H 0.892203 0.119312 0.756835 0.067 Uiso 1 1 calc R . . . .
C4 C 0.1637(2) 0.21510(18) 0.69139(19) 0.0616(6) Uani 1 1 d . . . . .
H4A H 0.170841 0.159087 0.732041 0.092 Uiso 1 1 calc GR . . . .
H4B H 0.078241 0.240507 0.688539 0.092 Uiso 1 1 calc GR . . . .
H4C H 0.225810 0.260321 0.721413 0.092 Uiso 1 1 calc GR . . . .
C12 C 0.4246(2) 0.66316(13) 0.55854(16) 0.0492(5) Uani 1 1 d . . . . .
H12 H 0.423510 0.726332 0.540988 0.059 Uiso 1 1 calc R . . . .
C9 C 0.2124(2) 0.63536(16) 0.45207(18) 0.0568(6) Uani 1 1 d . . . . .
H9 H 0.203734 0.698106 0.433200 0.068 Uiso 1 1 calc R . . . .
C8 C 0.1218(2) 0.57196(18) 0.4138(2) 0.0634(6) Uani 1 1 d . . . . .
H8 H 0.051269 0.592409 0.368269 0.076 Uiso 1 1 calc R . . . .
C21 C 0.7388(2) 0.07925(16) 0.65861(19) 0.0576(6) Uani 1 1 d . . . . .
H21 H 0.777788 0.025449 0.637556 0.069 Uiso 1 1 calc R . . . .
C3 C 0.0909(2) 0.11879(17) 0.5363(2) 0.0725(8) Uani 1 1 d . . . . .
H3A H 0.103525 0.106128 0.467149 0.109 Uiso 1 1 calc GR . . . .
H3B H 0.005208 0.142557 0.537136 0.109 Uiso 1 1 calc GR . . . .
H3C H 0.102136 0.061979 0.575446 0.109 Uiso 1 1 calc GR . . . .
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'
O O 0.0106 0.0060 '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 Ni1 N4 162.77(7) . . ?
N1 Ni1 N3 93.72(6) . . ?
N1 Ni1 N2 83.83(6) . . ?
N3 Ni1 N4 85.09(6) . . ?
N3 Ni1 N2 174.82(7) . . ?
N2 Ni1 N4 98.60(6) . . ?
C11 N4 Ni1 111.98(12) . . ?
C14 N4 Ni1 129.63(13) . . ?
C14 N4 C11 117.73(16) . . ?
C23 N1 Ni1 110.69(11) . . ?
C1 N1 Ni1 128.39(13) . . ?
C1 N1 C23 120.91(15) . . ?
C6 N3 Ni1 113.61(12) . . ?
C5 N3 Ni1 125.52(13) . . ?
C5 N3 C6 120.65(16) . . ?
C19 N2 Ni1 110.41(12) . . ?
C15 N2 Ni1 131.44(14) . . ?
C15 N2 C19 118.03(16) . . ?
C17 C18 C19 117.32(19) . . ?
C17 C18 C20 125.22(19) . . ?
C20 C18 C19 117.43(19) . . ?
N2 C19 C18 122.12(18) . . ?
N2 C19 C23 115.30(16) . . ?
C18 C19 C23 122.54(18) . . ?
N4 C11 C6 115.92(16) . . ?
N4 C11 C10 121.90(18) . . ?
C10 C11 C6 122.11(18) . . ?
N1 C23 C19 111.93(16) . . ?
C22 C23 N1 129.91(18) . . ?
C22 C23 C19 118.11(17) . . ?
N3 C6 C11 113.19(16) . . ?
C7 C6 N3 129.33(19) . . ?
C7 C6 C11 117.47(18) . . ?
N1 C1 C2 115.38(16) . . ?
O1 C1 N1 124.66(19) . . ?
O1 C1 C2 119.89(18) . . ?
N3 C5 C2 116.66(16) . . ?
O2 C5 N3 123.96(19) . . ?
O2 C5 C2 119.34(18) . . ?
C5 C2 C1 111.05(16) . . ?
C5 C2 C4 108.92(18) . . ?
C4 C2 C1 108.80(18) . . ?
C3 C2 C1 109.66(18) . . ?
C3 C2 C5 109.52(18) . . ?
C3 C2 C4 108.8(2) . . ?
C16 C17 C18 119.46(19) . . ?
N4 C14 C13 123.2(2) . . ?
C12 C10 C11 117.67(19) . . ?
C12 C10 C9 123.95(19) . . ?
C9 C10 C11 118.3(2) . . ?
C12 C13 C14 119.5(2) . . ?
C23 C22 C21 119.2(2) . . ?
N2 C15 C16 122.6(2) . . ?
C6 C7 C8 120.1(2) . . ?
C17 C16 C15 119.9(2) . . ?
C21 C20 C18 119.68(19) . . ?
C13 C12 C10 119.90(19) . . ?
C8 C9 C10 119.3(2) . . ?
C9 C8 C7 122.6(2) . . ?
C20 C21 C22 122.8(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
Ni1 N4 1.9209(16) . ?
Ni1 N1 1.8801(15) . ?
Ni1 N3 1.8806(16) . ?
Ni1 N2 1.9090(16) . ?
N4 C11 1.378(2) . ?
N4 C14 1.328(2) . ?
N1 C23 1.410(2) . ?
N1 C1 1.345(2) . ?
N3 C6 1.406(2) . ?
N3 C5 1.356(2) . ?
N2 C19 1.374(2) . ?
N2 C15 1.324(2) . ?
O1 C1 1.229(2) . ?
O2 C5 1.223(2) . ?
C18 C19 1.412(2) . ?
C18 C17 1.406(3) . ?
C18 C20 1.411(3) . ?
C19 C23 1.413(3) . ?
C11 C6 1.414(3) . ?
C11 C10 1.413(3) . ?
C23 C22 1.380(3) . ?
C6 C7 1.383(3) . ?
C1 C2 1.540(3) . ?
C5 C2 1.536(3) . ?
C2 C4 1.540(3) . ?
C2 C3 1.530(3) . ?
C17 C16 1.362(3) . ?
C14 C13 1.400(3) . ?
C10 C12 1.404(3) . ?
C10 C9 1.410(3) . ?
C13 C12 1.355(3) . ?
C22 C21 1.414(3) . ?
C15 C16 1.398(3) . ?
C7 C8 1.410(3) . ?
C20 C21 1.362(3) . ?
C9 C8 1.354(4) . ?
