#------------------------------------------------------------------------------
#$Date: 2022-03-10 23:56:44 +0100 (jue 10 de mar de 2022) $
#$Revision: 273614 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129796.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_7129796
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 H17 N5 O2'
_chemical_formula_sum            'C21 H17 N5 O2'
_chemical_formula_weight         371.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 109.1040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2961(3)
_cell_length_b                   19.4180(8)
_cell_length_c                   11.7921(5)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.80
_cell_volume                     1795.01(12)
_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      297.39
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0194
_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       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20692
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        23.553
_diffrn_reflns_theta_max         23.553
_diffrn_reflns_theta_min         2.098
_exptl_absorpt_coefficient_mu    0.093
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0347
_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)+(0.0445P)²+0.3717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2201
_reflns_number_total             2672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00639a2.cif
_cod_data_source_block           l7_a
_cod_database_code               7129796
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C12(H12), C7(H7), C14(H14), C10(H10), C5(H5), C11(H11),
 C16(H16), C15(H15), C6(H6), C21(H21), C19(H19), C20(H20)
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+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36528(15) 0.43905(6) 0.41436(10) 0.0555(3) Uani 1 1 d . . . . .
O2 O 0.86189(15) 0.37404(7) 0.53856(11) 0.0630(4) Uani 1 1 d . . . . .
N5 N 0.64414(17) 0.43710(7) 0.41556(11) 0.0480(3) Uani 1 1 d . . . . .
N3 N 0.60016(17) 0.36055(7) 0.55691(11) 0.0486(3) Uani 1 1 d . . . . .
H3 H 0.495571 0.373596 0.528038 0.058 Uiso 1 1 calc R . . . .
N4 N 0.36530(17) 0.33990(7) 0.66257(12) 0.0517(4) Uani 1 1 d . . . . .
N1 N 0.43483(19) 0.49487(7) 0.26865(12) 0.0576(4) Uani 1 1 d . . . . .
H1 H 0.518038 0.502542 0.241985 0.069 Uiso 1 1 calc R . . . .
N2 N 0.4380(2) 0.56509(7) 0.08119(13) 0.0605(4) Uani 1 1 d . . . . .
C1 C 0.4725(2) 0.45608(8) 0.36938(14) 0.0453(4) Uani 1 1 d . . . . .
C4 C 0.6397(2) 0.31194(8) 0.65052(14) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.5129(2) 0.30326(8) 0.70628(13) 0.0454(4) Uani 1 1 d . . . . .
C3 C 0.7108(2) 0.38842(8) 0.50851(14) 0.0457(4) Uani 1 1 d . . . . .
C13 C 0.2778(2) 0.52419(8) 0.20205(14) 0.0503(4) Uani 1 1 d . . . . .
C8 C 0.5425(2) 0.25648(8) 0.80348(14) 0.0513(4) Uani 1 1 d . . . . .
C18 C 0.2858(2) 0.56332(8) 0.10161(14) 0.0522(4) Uani 1 1 d . . . . .
C12 C 0.2486(2) 0.33084(10) 0.71436(17) 0.0609(5) Uani 1 1 d . . . . .
H12 H 0.146979 0.355219 0.684393 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6953(3) 0.21847(10) 0.84092(17) 0.0651(5) Uani 1 1 d . . . . .
H7 H 0.716599 0.188016 0.905021 0.078 Uiso 1 1 calc R . . . .
C14 C 0.1272(2) 0.51828(9) 0.22408(16) 0.0593(5) Uani 1 1 d . . . . .
H14 H 0.121196 0.492246 0.288764 0.071 Uiso 1 1 calc R . . . .
C10 C 0.4136(3) 0.24991(9) 0.85601(16) 0.0611(5) Uani 1 1 d . . . . .
H10 H 0.428429 0.220409 0.920758 0.073 Uiso 1 1 calc R . . . .
C5 C 0.7854(2) 0.27329(9) 0.68844(17) 0.0626(5) Uani 1 1 d . . . . .
H5 H 0.867888 0.278039 0.651295 0.075 Uiso 1 1 calc R . . . .
C2 C 0.7718(2) 0.47263(11) 0.37524(18) 0.0684(5) Uani 1 1 d . . . . .
H2A H 0.755569 0.460600 0.293282 0.103 Uiso 1 1 calc GR . . . .
H2B H 0.884060 0.459036 0.424705 0.103 Uiso 1 1 calc GR . . . .
H2C H 0.759320 0.521510 0.381366 0.103 Uiso 1 1 calc GR . . . .
C17 C 0.1384(3) 0.59681(9) 0.02769(15) 0.0609(5) Uani 1 1 d . . . . .
C11 C 0.2679(3) 0.28674(10) 0.81186(17) 0.0650(5) Uani 1 1 d . . . . .
H11 H 0.181774 0.282806 0.845850 0.078 Uiso 1 1 calc R . . . .
C16 C -0.0145(3) 0.59010(10) 0.05398(18) 0.0715(6) Uani 1 1 d . . . . .
H16 H -0.112728 0.612149 0.006077 0.086 Uiso 1 1 calc R . . . .
C15 C -0.0195(3) 0.55172(10) 0.14861(18) 0.0689(5) Uani 1 1 d . . . . .
H15 H -0.121931 0.547325 0.164149 0.083 Uiso 1 1 calc R . . . .
C6 C 0.8107(3) 0.22628(10) 0.78370(19) 0.0716(6) Uani 1 1 d . . . . .
H6 H 0.909714 0.199914 0.807784 0.086 Uiso 1 1 calc R . . . .
C21 C 0.4448(3) 0.60056(10) -0.01255(17) 0.0731(6) Uani 1 1 d . . . . .
H21 H 0.547676 0.601946 -0.028082 0.088 Uiso 1 1 calc R . . . .
C19 C 0.1538(3) 0.63434(11) -0.06977(18) 0.0790(6) Uani 1 1 d . . . . .
H19 H 0.060310 0.657891 -0.120487 0.095 Uiso 1 1 calc R . . . .
C20 C 0.3055(3) 0.63618(11) -0.08978(18) 0.0829(7) Uani 1 1 d . . . . .
H20 H 0.316844 0.660905 -0.154286 0.100 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'
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
C1 N5 C3 124.61(13) . . ?
C1 N5 C2 120.08(13) . . ?
C3 N5 C2 115.11(14) . . ?
C4 N3 H3 117.0 . . ?
C3 N3 H3 117.0 . . ?
C3 N3 C4 125.96(14) . . ?
C12 N4 C9 117.47(15) . . ?
C1 N1 H1 115.8 . . ?
C1 N1 C13 128.49(15) . . ?
C13 N1 H1 115.8 . . ?
C21 N2 C18 117.24(17) . . ?
O1 C1 N5 123.62(14) . . ?
O1 C1 N1 122.67(15) . . ?
N1 C1 N5 113.71(15) . . ?
N3 C4 C9 115.11(14) . . ?
C5 C4 N3 125.38(16) . . ?
C5 C4 C9 119.50(15) . . ?
N4 C9 C4 118.19(14) . . ?
N4 C9 C8 122.44(15) . . ?
C8 C9 C4 119.36(15) . . ?
O2 C3 N5 118.83(15) . . ?
O2 C3 N3 124.42(15) . . ?
N3 C3 N5 116.75(14) . . ?
N1 C13 C18 113.19(16) . . ?
C14 C13 N1 126.94(15) . . ?
C14 C13 C18 119.87(16) . . ?
C7 C8 C9 119.31(16) . . ?
C10 C8 C9 117.25(16) . . ?
C10 C8 C7 123.43(16) . . ?
N2 C18 C13 117.26(15) . . ?
N2 C18 C17 123.17(16) . . ?
C17 C18 C13 119.55(18) . . ?
N4 C12 H12 118.0 . . ?
N4 C12 C11 124.03(17) . . ?
C11 C12 H12 118.0 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.88(17) . . ?
C6 C7 H7 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.83(18) . . ?
C15 C14 H14 120.1 . . ?
C8 C10 H10 120.2 . . ?
C11 C10 C8 119.66(17) . . ?
C11 C10 H10 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.09(18) . . ?
C6 C5 H5 120.0 . . ?
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 . . ?
C16 C17 C18 118.95(17) . . ?
C19 C17 C18 117.0(2) . . ?
C19 C17 C16 124.04(19) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.13(18) . . ?
C10 C11 H11 120.4 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.37(18) . . ?
C15 C16 H16 119.8 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C7 C6 C5 121.80(18) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N2 C21 H21 118.3 . . ?
N2 C21 C20 123.5(2) . . ?
C20 C21 H21 118.3 . . ?
C17 C19 H19 120.1 . . ?
C20 C19 C17 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
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
O1 C1 1.2211(19) . ?
O2 C3 1.2183(19) . ?
N5 C1 1.397(2) . ?
N5 C3 1.416(2) . ?
N5 C2 1.467(2) . ?
N3 H3 0.8600 . ?
N3 C4 1.4071(19) . ?
N3 C3 1.343(2) . ?
N4 C9 1.363(2) . ?
N4 C12 1.315(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.354(2) . ?
N1 C13 1.403(2) . ?
N2 C18 1.362(2) . ?
N2 C21 1.319(2) . ?
C4 C9 1.422(2) . ?
C4 C5 1.368(2) . ?
C9 C8 1.419(2) . ?
C13 C18 1.427(2) . ?
C13 C14 1.361(2) . ?
C8 C7 1.407(2) . ?
C8 C10 1.406(2) . ?
C18 C17 1.407(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.400(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.348(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.353(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.409(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C17 C16 1.407(3) . ?
C17 C19 1.402(3) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.354(3) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.398(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.354(3) . ?
C20 H20 0.9300 . ?
