#------------------------------------------------------------------------------
#$Date: 2022-03-10 23:56:44 +0100 (jue 10 de mar de 2022) $
#$Revision: 273614 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129795.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_7129795
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         'C22 H18 N4 O2'
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         384.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-09-06 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                100.17(2)
_cell_angle_beta                 92.23(3)
_cell_angle_gamma                98.55(3)
_cell_formula_units_Z            2
_cell_length_a                   7.835(6)
_cell_length_b                   7.929(5)
_cell_length_c                   15.763(11)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.80
_cell_volume                     951.0(12)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_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  0.0420
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.174
_diffrn_reflns_theta_max         25.174
_diffrn_reflns_theta_min         2.631
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7052
_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            white
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             404.0
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0380
_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)+(0.0302P)²+0.3629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2619
_reflns_number_total             3422
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00639a2.cif
_cod_data_source_block           L2_0m_a
_cod_database_code               7129795
_shelx_shelxl_version_number     2017/1
_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.
;
_refine_ls_ext_reflns_number_totalnction_coef 0.034(3)
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O4 O 0.40197(16) 0.50895(19) 0.30426(8) 0.0689(4) Uani 1 1 d . . . . .
O3 O 0.07014(19) 0.79799(17) 0.25365(8) 0.0686(4) Uani 1 1 d . . . . .
N7 N 0.27389(18) 0.65929(18) 0.41225(8) 0.0510(4) Uani 1 1 d . . . . .
H7 H 0.175455 0.687340 0.426206 0.061 Uiso 1 1 calc R U . . .
N6 N 0.19925(17) 0.86009(18) 0.55360(9) 0.0499(4) Uani 1 1 d . . . . .
N8 N 0.1521(2) 0.61288(18) 0.14344(8) 0.0560(4) Uani 1 1 d . . . . .
H8 H 0.161580 0.505556 0.126923 0.067 Uiso 1 1 calc R U . . .
N9 N 0.2585(2) 0.46260(18) -0.00364(9) 0.0576(4) Uani 1 1 d . . . . .
C7 C 0.3667(2) 0.8310(2) 0.55035(10) 0.0421(4) Uani 1 1 d . . . . .
C9 C 0.2734(2) 0.5589(2) 0.33368(10) 0.0485(4) Uani 1 1 d . . . . .
C8 C 0.4113(2) 0.7246(2) 0.47444(10) 0.0435(4) Uani 1 1 d . . . . .
C1 C 0.5779(2) 0.6933(2) 0.46739(11) 0.0515(4) Uani 1 1 d . . . . .
H1 H 0.607520 0.622960 0.418234 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1023(2) 0.6548(2) 0.22432(10) 0.0483(4) Uani 1 1 d . . . . .
C19 C 0.2524(2) 0.6355(2) 0.00484(10) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.0968(2) 0.5132(2) 0.28027(10) 0.0496(4) Uani 1 1 d . . . . .
C30 C 0.1906(2) 0.7196(2) 0.08241(10) 0.0471(4) Uani 1 1 d . . . . .
C2 C 0.7038(2) 0.7678(2) 0.53477(12) 0.0577(5) Uani 1 1 d . . . . .
H2 H 0.816936 0.746959 0.529123 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4946(2) 0.9031(2) 0.61744(10) 0.0470(4) Uani 1 1 d . . . . .
C18 C 0.3055(2) 0.7325(2) -0.05898(10) 0.0494(4) Uani 1 1 d . . . . .
C3 C 0.6649(2) 0.8694(2) 0.60782(12) 0.0568(5) Uani 1 1 d . . . . .
H3 H 0.750713 0.916787 0.651528 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1606(2) 0.9616(2) 0.62324(12) 0.0572(5) Uani 1 1 d . . . . .
H6 H 0.047676 0.984485 0.625864 0.069 Uiso 1 1 calc R U . . .
C20 C 0.3724(2) 0.6435(2) -0.13266(11) 0.0584(5) Uani 1 1 d . . . . .
H20 H 0.412269 0.702701 -0.175747 0.070 Uiso 1 1 calc R U . . .
C29 C 0.3786(3) 0.4727(3) -0.14050(11) 0.0647(5) Uani 1 1 d . . . . .
H29 H 0.421981 0.412615 -0.188927 0.078 Uiso 1 1 calc R U . . .
C00M C 0.2778(2) 1.0374(2) 0.69362(12) 0.0623(5) Uani 1 1 d . . . . .
H00M H 0.242582 1.106873 0.741548 0.075 Uiso 1 1 calc R U . . .
C15 C 0.1761(3) 0.8915(2) 0.09256(12) 0.0604(5) Uani 1 1 d . . . . .
H15 H 0.134045 0.946566 0.142691 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4437(2) 1.0079(2) 0.69077(11) 0.0592(5) Uani 1 1 d . . . . .
H5 H 0.523416 1.056544 0.737047 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0861(3) 0.3291(2) 0.22805(12) 0.0618(5) Uani 1 1 d . . . . .
H12A H -0.009799 0.305936 0.185641 0.093 Uiso 1 1 calc R U . . .
H12B H 0.070057 0.246844 0.266163 0.093 Uiso 1 1 calc R U . . .
H12C H 0.191278 0.319129 0.199653 0.093 Uiso 1 1 calc R U . . .
C22 C 0.3187(3) 0.3875(2) -0.07460(12) 0.0682(6) Uani 1 1 d . . . . .
H22 H 0.321828 0.269111 -0.081517 0.082 Uiso 1 1 calc R U . . .
C11 C -0.0589(2) 0.5225(3) 0.33600(11) 0.0640(5) Uani 1 1 d . . . . .
H11A H -0.163736 0.479041 0.300298 0.096 Uiso 1 1 calc R U . . .
H11B H -0.060054 0.640856 0.362772 0.096 Uiso 1 1 calc R U . . .
H11C H -0.050346 0.453501 0.379805 0.096 Uiso 1 1 calc R U . . .
C16 C 0.2250(3) 0.9853(2) 0.02716(13) 0.0716(6) Uani 1 1 d . . . . .
H16 H 0.212887 1.101751 0.034167 0.086 Uiso 1 1 calc R U . . .
C17 C 0.2895(3) 0.9086(2) -0.04613(13) 0.0677(5) Uani 1 1 d . . . . .
H17 H 0.323315 0.973544 -0.088018 0.081 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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
C9 N7 C8 129.45(15) . . ?
C9 N7 H7 115.3 . . ?
C8 N7 H7 115.3 . . ?
C6 N6 C7 116.83(15) . . ?
C13 N8 C30 129.14(15) . . ?
C13 N8 H8 115.4 . . ?
C30 N8 H8 115.4 . . ?
C22 N9 C19 116.90(15) . . ?
N6 C7 C4 122.99(15) . . ?
N6 C7 C8 117.42(14) . . ?
C4 C7 C8 119.57(15) . . ?
O4 C9 N7 123.36(17) . . ?
O4 C9 C10 120.88(15) . . ?
N7 C9 C10 115.74(14) . . ?
C1 C8 N7 125.55(15) . . ?
C1 C8 C7 119.77(15) . . ?
N7 C8 C7 114.67(14) . . ?
C8 C1 C2 119.71(16) . . ?
C8 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
O3 C13 N8 122.53(16) . . ?
O3 C13 C10 121.08(15) . . ?
N8 C13 C10 116.32(15) . . ?
N9 C19 C18 122.90(15) . . ?
N9 C19 C30 117.54(14) . . ?
C18 C19 C30 119.57(15) . . ?
C11 C10 C12 109.68(15) . . ?
C11 C10 C13 108.41(15) . . ?
C12 C10 C13 113.94(14) . . ?
C11 C10 C9 113.41(14) . . ?
C12 C10 C9 107.53(15) . . ?
C13 C10 C9 103.87(14) . . ?
C15 C30 N8 125.76(15) . . ?
C15 C30 C19 119.69(15) . . ?
N8 C30 C19 114.54(15) . . ?
C3 C2 C1 121.78(17) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C7 C4 C3 119.20(15) . . ?
C7 C4 C5 117.22(16) . . ?
C3 C4 C5 123.58(16) . . ?
C17 C18 C20 124.07(16) . . ?
C17 C18 C19 119.06(16) . . ?
C20 C18 C19 116.87(16) . . ?
C2 C3 C4 119.96(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N6 C6 C00M 124.40(17) . . ?
N6 C6 H6 117.8 . . ?
C00M C6 H6 117.8 . . ?
C29 C20 C18 119.90(17) . . ?
C29 C20 H20 120.0 . . ?
C18 C20 H20 120.0 . . ?
C20 C29 C22 118.74(17) . . ?
C20 C29 H29 120.6 . . ?
C22 C29 H29 120.6 . . ?
C5 C00M C6 118.87(17) . . ?
C5 C00M H00M 120.6 . . ?
C6 C00M H00M 120.6 . . ?
C30 C15 C16 119.98(17) . . ?
C30 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C00M C5 C4 119.67(17) . . ?
C00M C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N9 C22 C29 124.64(18) . . ?
N9 C22 H22 117.7 . . ?
C29 C22 H22 117.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C16 C15 121.15(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.48(17) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
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
O4 C9 1.215(2) . ?
O3 C13 1.214(2) . ?
N7 C9 1.348(2) . ?
N7 C8 1.400(2) . ?
N7 H7 0.8600 . ?
N6 C6 1.316(2) . ?
N6 C7 1.366(2) . ?
N8 C13 1.347(2) . ?
N8 C30 1.402(2) . ?
N8 H8 0.8600 . ?
N9 C22 1.311(2) . ?
N9 C19 1.362(2) . ?
C7 C4 1.409(2) . ?
C7 C8 1.425(2) . ?
C9 C10 1.552(3) . ?
C8 C1 1.369(2) . ?
C1 C2 1.405(3) . ?
C1 H1 0.9300 . ?
C13 C10 1.542(2) . ?
C19 C18 1.410(2) . ?
C19 C30 1.424(2) . ?
C10 C11 1.533(2) . ?
C10 C12 1.533(3) . ?
C30 C15 1.367(3) . ?
C2 C3 1.357(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.408(3) . ?
C4 C5 1.407(2) . ?
C18 C17 1.400(3) . ?
C18 C20 1.411(2) . ?
C3 H3 0.9300 . ?
C6 C00M 1.399(3) . ?
C6 H6 0.9300 . ?
C20 C29 1.346(3) . ?
C20 H20 0.9300 . ?
C29 C22 1.395(3) . ?
C29 H29 0.9300 . ?
C00M C5 1.355(3) . ?
C00M H00M 0.9300 . ?
C15 C16 1.406(3) . ?
C15 H15 0.9300 . ?
C5 H5 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C22 H22 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C16 C17 1.360(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
