#------------------------------------------------------------------------------
#$Date: 2022-03-11 00:56:44 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273614 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129797.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_7129797
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         'C21 H15 N5 Ni O2'
_chemical_formula_sum            'C21 H15 N5 Ni O2'
_chemical_formula_weight         428.09
_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
_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                96.460(14)
_cell_angle_beta                 109.436(10)
_cell_angle_gamma                103.717(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0529(19)
_cell_length_b                   10.359(3)
_cell_length_c                   11.497(3)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.80
_cell_volume                     859.2(4)
_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      298.89
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0413
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33649
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.410
_diffrn_reflns_theta_min         1.921
_exptl_absorpt_coefficient_mu    1.160
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6680
_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    1.655
_exptl_crystal_description       Block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0322
_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)+(0.0346P)²+0.2391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4641
_reflns_number_total             5637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00639a2.cif
_cod_data_source_block           sa-2
_cod_database_code               7129797
_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.
;
_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:
 C20(H20), C12(H12), C19(H19), C13(H13), C14(H14), C5(H5), C15(H15), C18(H18),
 C11(H11), C10(H10), C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Ni1 Ni 0.72132(3) 0.40975(2) 0.34208(2) 0.02986(6) Uani 1 1 d . . . . .
N3 N 0.66196(18) 0.38239(13) 0.16872(12) 0.0335(3) Uani 1 1 d . . . . .
O1 O 1.01890(19) 0.77240(13) 0.32423(13) 0.0533(3) Uani 1 1 d . . . . .
N1 N 0.82615(18) 0.59577(12) 0.36343(12) 0.0332(3) Uani 1 1 d . . . . .
N2 N 0.72153(17) 0.45347(13) 0.50896(12) 0.0329(3) Uani 1 1 d . . . . .
N4 N 0.63178(18) 0.21594(13) 0.31139(13) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.6885(2) 0.43417(16) -0.01371(12) 0.0585(4) Uani 1 1 d . . . . .
N5 N 0.86970(19) 0.58528(14) 0.16910(13) 0.0372(3) Uani 1 1 d . . . . .
C17 C 0.7854(2) 0.59171(16) 0.55673(14) 0.0324(3) Uani 1 1 d . . . . .
C21 C 0.8404(2) 0.67267(15) 0.47654(14) 0.0336(3) Uani 1 1 d . . . . .
C4 C 0.5259(2) 0.25780(15) 0.10638(15) 0.0350(3) Uani 1 1 d . . . . .
C3 C 0.7312(2) 0.46253(17) 0.10089(15) 0.0372(3) Uani 1 1 d . . . . .
C9 C 0.5170(2) 0.16511(15) 0.18741(15) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.9091(2) 0.65738(16) 0.28983(15) 0.0355(3) Uani 1 1 d . . . . .
C20 C 0.8862(2) 0.81247(17) 0.51516(18) 0.0435(4) Uani 1 1 d . . . . .
H20 H 0.917381 0.868513 0.463246 0.052 Uiso 1 1 calc R . . . .
C12 C 0.6548(2) 0.12906(17) 0.38851(18) 0.0420(4) Uani 1 1 d . . . . .
H12 H 0.739731 0.160955 0.470850 0.050 Uiso 1 1 calc R . . . .
C16 C 0.7827(2) 0.64990(18) 0.67321(15) 0.0397(4) Uani 1 1 d . . . . .
C19 C 0.8862(3) 0.87077(19) 0.6318(2) 0.0517(5) Uani 1 1 d . . . . .
H19 H 0.918882 0.964878 0.655722 0.062 Uiso 1 1 calc R . . . .
C8 C 0.4038(2) 0.02902(17) 0.14331(19) 0.0467(4) Uani 1 1 d . . . . .
C13 C 0.6474(3) 0.37523(19) 0.57336(16) 0.0418(4) Uani 1 1 d . . . . .
H13 H 0.597499 0.282437 0.539691 0.050 Uiso 1 1 calc R . . . .
C14 C 0.6405(3) 0.4253(2) 0.68943(17) 0.0471(4) Uani 1 1 d . . . . .
H14 H 0.588460 0.366192 0.731501 0.056 Uiso 1 1 calc R . . . .
C5 C 0.4057(2) 0.21516(19) -0.01775(17) 0.0454(4) Uani 1 1 d . . . . .
H5 H 0.405797 0.273607 -0.073498 0.055 Uiso 1 1 calc R . . . .
C15 C 0.7104(3) 0.5610(2) 0.74053(16) 0.0469(4) Uani 1 1 d . . . . .
H15 H 0.710468 0.594739 0.819002 0.056 Uiso 1 1 calc R . . . .
C18 C 0.8396(3) 0.7932(2) 0.71085(18) 0.0505(5) Uani 1 1 d . . . . .
H18 H 0.845058 0.834167 0.788829 0.061 Uiso 1 1 calc R . . . .
C11 C 0.5543(3) -0.00918(19) 0.3488(2) 0.0547(5) Uani 1 1 d . . . . .
H11 H 0.574834 -0.067704 0.404236 0.066 Uiso 1 1 calc R . . . .
C10 C 0.4266(3) -0.05778(19) 0.2293(2) 0.0587(5) Uani 1 1 d . . . . .
H10 H 0.354756 -0.148111 0.204670 0.070 Uiso 1 1 calc R . . . .
C2 C 0.9698(3) 0.6552(2) 0.09712(18) 0.0468(4) Uani 1 1 d . . . . .
H2A H 0.950981 0.592864 0.022317 0.070 Uiso 1 1 calc GR . . . .
H2B H 1.098872 0.688164 0.148023 0.070 Uiso 1 1 calc GR . . . .
H2C H 0.924842 0.730241 0.074014 0.070 Uiso 1 1 calc GR . . . .
C7 C 0.2820(3) -0.0102(2) 0.0155(2) 0.0585(6) Uani 1 1 d . . . . .
H7 H 0.202754 -0.098139 -0.016664 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2823(3) 0.0819(2) -0.0598(2) 0.0575(5) Uani 1 1 d . . . . .
H6 H 0.197812 0.056335 -0.142514 0.069 Uiso 1 1 calc R . . . .
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
N3 Ni1 N1 92.07(6) . . ?
N3 Ni1 N2 164.05(6) . . ?
N3 Ni1 N4 84.43(6) . . ?
N1 Ni1 N2 85.41(6) . . ?
N1 Ni1 N4 173.76(6) . . ?
N4 Ni1 N2 99.35(6) . . ?
C4 N3 Ni1 111.19(11) . . ?
C3 N3 Ni1 129.32(11) . . ?
C3 N3 C4 119.49(13) . . ?
C21 N1 Ni1 113.98(11) . . ?
C1 N1 Ni1 126.18(11) . . ?
C1 N1 C21 119.20(13) . . ?
C17 N2 Ni1 111.75(10) . . ?
C13 N2 Ni1 129.91(12) . . ?
C13 N2 C17 117.53(14) . . ?
C9 N4 Ni1 110.10(11) . . ?
C12 N4 Ni1 131.58(12) . . ?
C12 N4 C9 118.23(14) . . ?
C3 N5 C2 115.29(14) . . ?
C1 N5 C3 128.86(14) . . ?
C1 N5 C2 115.33(14) . . ?
N2 C17 C21 115.48(13) . . ?
N2 C17 C16 122.32(15) . . ?
C16 C17 C21 122.01(15) . . ?
N1 C21 C17 113.17(13) . . ?
C20 C21 N1 129.50(16) . . ?
C20 C21 C17 117.14(15) . . ?
N3 C4 C9 112.38(13) . . ?
C5 C4 N3 130.02(16) . . ?
C5 C4 C9 117.60(15) . . ?
N3 C3 N5 116.80(13) . . ?
O2 C3 N3 125.04(16) . . ?
O2 C3 N5 118.09(15) . . ?
N4 C9 C4 114.98(13) . . ?
N4 C9 C8 122.40(16) . . ?
C8 C9 C4 122.57(16) . . ?
O1 C1 N1 123.93(15) . . ?
O1 C1 N5 117.88(15) . . ?
N1 C1 N5 118.19(13) . . ?
C21 C20 H20 119.5 . . ?
C21 C20 C19 120.94(18) . . ?
C19 C20 H20 119.5 . . ?
N4 C12 H12 119.1 . . ?
N4 C12 C11 121.84(17) . . ?
C11 C12 H12 119.1 . . ?
C17 C16 C18 118.43(17) . . ?
C15 C16 C17 117.56(16) . . ?
C15 C16 C18 123.83(16) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 C20 121.89(17) . . ?
C18 C19 H19 119.1 . . ?
C9 C8 C7 117.67(18) . . ?
C10 C8 C9 116.99(17) . . ?
C10 C8 C7 125.29(17) . . ?
N2 C13 H13 118.3 . . ?
N2 C13 C14 123.32(17) . . ?
C14 C13 H13 118.3 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.76(17) . . ?
C15 C14 H14 120.1 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.65(19) . . ?
C6 C5 H5 120.2 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.36(16) . . ?
C14 C15 H15 120.3 . . ?
C16 C18 H18 120.3 . . ?
C19 C18 C16 119.46(16) . . ?
C19 C18 H18 120.3 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.13(19) . . ?
C10 C11 H11 119.9 . . ?
C8 C10 H10 120.1 . . ?
C11 C10 C8 119.82(17) . . ?
C11 C10 H10 120.1 . . ?
N5 C2 H2A 109.5 . . ?
N5 C2 H2B 109.5 . . ?
N5 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C7 H7 120.4 . . ?
C6 C7 C8 119.29(17) . . ?
C6 C7 H7 120.4 . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.86(18) . . ?
C7 C6 H6 118.6 . . ?
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 N3 1.8591(14) . ?
Ni1 N1 1.8628(13) . ?
Ni1 N2 1.9206(14) . ?
Ni1 N4 1.9131(14) . ?
N3 C4 1.4066(19) . ?
N3 C3 1.351(2) . ?
O1 C1 1.2326(19) . ?
N1 C21 1.401(2) . ?
N1 C1 1.366(2) . ?
N2 C17 1.379(2) . ?
N2 C13 1.327(2) . ?
N4 C9 1.374(2) . ?
N4 C12 1.334(2) . ?
O2 C3 1.226(2) . ?
N5 C3 1.413(2) . ?
N5 C1 1.395(2) . ?
N5 C2 1.470(2) . ?
C17 C21 1.421(2) . ?
C17 C16 1.415(2) . ?
C21 C20 1.387(2) . ?
C4 C9 1.417(2) . ?
C4 C5 1.380(2) . ?
C9 C8 1.413(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.408(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.404(2) . ?
C16 C15 1.411(3) . ?
C16 C18 1.415(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.364(3) . ?
C8 C10 1.406(3) . ?
C8 C7 1.416(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.417(3) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.363(3) . ?
C10 H10 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.358(3) . ?
C6 H6 0.9300 . ?
