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#$Date: 2024-12-06 22:20:58 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296642 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063506.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_7063506
loop_
_publ_author_name
'Pandey, Ankit'
'Balakrishna, Maravanji S.'
_publ_section_title
;
 Catalytic utility of a bimetallic (pincer) PNN-based nickel complex in
 the synthesis of quinolines and α-alkylation of ketones
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19549
_journal_page_last               19560
_journal_paper_doi               10.1039/D4NJ04250F
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C48 H36 N4 O2 P2'
_chemical_formula_sum            'C48 H36 N4 O2 P2'
_chemical_formula_weight         762.75
_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     iterative
_audit_creation_date             2024-10-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.037(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.147(2)
_cell_length_b                   13.350(3)
_cell_length_c                   16.012(4)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.54
_cell_volume                     1954.9(8)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39433
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.986
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1197 before and 0.0893 after correction. The Ratio of minimum to maximum transmission is 0.8625. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       needle
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0541
_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)+(0.0306P)²+3.0345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2754
_reflns_number_total             3434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04250f2.cif
_cod_data_source_block           msb_ap_l2_n_a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7063506--7063508.cif.'
_cod_database_code               7063506
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C9(H9), C20(H20), C10(H10), C3(H3), C21(H21), C11(H11),
 C12(H12), C14(H14), C4(H4), C22(H22), C24(H24), C18(H18), C17(H17), C16(H16),
 C15(H15), C23(H23)
;
_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
P1 P 0.60072(9) 0.35393(6) 0.82917(5) 0.0360(2) Uani 1 1 d . . . . .
O1 O 0.5855(2) 0.43592(19) 0.66548(13) 0.0470(6) Uani 1 1 d . . . . .
N1 N 0.9158(3) 0.4658(2) 0.40135(15) 0.0383(6) Uani 1 1 d . . . . .
N2 N 0.8106(3) 0.4879(2) 0.62017(15) 0.0400(7) Uani 1 1 d . . . . .
H2 H 0.895089 0.510720 0.639245 0.048 Uiso 1 1 calc R . . . .
C1 C 0.9270(3) 0.4820(2) 0.48431(18) 0.0332(7) Uani 1 1 d . . . . .
C8 C 0.6977(3) 0.4747(2) 0.83503(18) 0.0344(7) Uani 1 1 d . . . . .
C2 C 0.8022(4) 0.4673(2) 0.53443(18) 0.0357(7) Uani 1 1 d . . . . .
C19 C 0.4093(3) 0.3928(2) 0.83499(18) 0.0362(7) Uani 1 1 d . . . . .
C7 C 0.7438(3) 0.5218(2) 0.76123(18) 0.0352(7) Uani 1 1 d . . . . .
C6 C 0.7033(4) 0.4768(3) 0.67771(19) 0.0388(8) Uani 1 1 d . . . . .
C5 C 0.7900(4) 0.4372(3) 0.3658(2) 0.0425(8) Uani 1 1 d . . . . .
H5 H 0.785712 0.428465 0.306972 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7356(4) 0.5199(2) 0.91063(19) 0.0393(8) Uani 1 1 d . . . . .
H9 H 0.708091 0.488305 0.961132 0.047 Uiso 1 1 calc R . . . .
C20 C 0.3615(4) 0.4863(3) 0.8604(2) 0.0408(8) Uani 1 1 d . . . . .
H20 H 0.431256 0.536266 0.875319 0.049 Uiso 1 1 calc R . . . .
C10 C 0.8126(4) 0.6099(3) 0.9149(2) 0.0436(8) Uani 1 1 d . . . . .
H10 H 0.837430 0.638920 0.967475 0.052 Uiso 1 1 calc R . . . .
C13 C 0.6372(4) 0.3038(2) 0.9340(2) 0.0391(8) Uani 1 1 d . . . . .
C3 C 0.6740(4) 0.4347(3) 0.4959(2) 0.0435(8) Uani 1 1 d . . . . .
H3 H 0.590218 0.422291 0.528489 0.052 Uiso 1 1 calc R . . . .
C21 C 0.2138(4) 0.5081(3) 0.8644(2) 0.0457(9) Uani 1 1 d . . . . .
H21 H 0.182870 0.572309 0.882707 0.055 Uiso 1 1 calc R . . . .
C11 C 0.8522(4) 0.6563(3) 0.8415(2) 0.0464(9) Uani 1 1 d . . . . .
H11 H 0.902696 0.718463 0.843268 0.056 Uiso 1 1 calc R . . . .
C12 C 0.8183(4) 0.6119(3) 0.7654(2) 0.0426(8) Uani 1 1 d . . . . .
H12 H 0.846604 0.643865 0.715177 0.051 Uiso 1 1 calc R . . . .
C14 C 0.5324(4) 0.2905(3) 0.9947(2) 0.0461(9) Uani 1 1 d . . . . .
H14 H 0.435143 0.313229 0.985035 0.055 Uiso 1 1 calc R . . . .
C4 C 0.6668(4) 0.4200(3) 0.4106(2) 0.0469(9) Uani 1 1 d . . . . .
H4 H 0.578736 0.398562 0.383776 0.056 Uiso 1 1 calc R . . . .
C22 C 0.1120(4) 0.4370(3) 0.8419(2) 0.0518(10) Uani 1 1 d . . . . .
H22 H 0.010620 0.452084 0.844108 0.062 Uiso 1 1 calc R . . . .
C24 C 0.3044(4) 0.3225(3) 0.8118(2) 0.0507(9) Uani 1 1 d . . . . .
H24 H 0.334221 0.258511 0.792507 0.061 Uiso 1 1 calc R . . . .
C18 C 0.7801(4) 0.2685(3) 0.9513(2) 0.0546(10) Uani 1 1 d . . . . .
H18 H 0.853460 0.276462 0.910621 0.066 Uiso 1 1 calc R . . . .
C17 C 0.8147(5) 0.2235(3) 1.0250(3) 0.0638(12) Uani 1 1 d . . . . .
H17 H 0.911799 0.200866 1.035328 0.077 Uiso 1 1 calc R . . . .
C16 C 0.7105(6) 0.2102(3) 1.0851(3) 0.0660(12) Uani 1 1 d . . . . .
H16 H 0.735252 0.178308 1.136485 0.079 Uiso 1 1 calc R . . . .
C15 C 0.5703(5) 0.2435(3) 1.0699(2) 0.0593(11) Uani 1 1 d . . . . .
H15 H 0.498177 0.234367 1.111200 0.071 Uiso 1 1 calc R . . . .
C23 C 0.1569(4) 0.3444(3) 0.8163(3) 0.0597(11) Uani 1 1 d . . . . .
H23 H 0.086482 0.294906 0.801630 0.072 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'
P P 0.1023 0.0942 '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
C19 P1 C8 102.09(14) . . ?
C19 P1 C13 102.45(14) . . ?
C13 P1 C8 101.15(15) . . ?
C5 N1 C1 121.1(3) . . ?
C2 N2 H2 116.1 . . ?
C6 N2 H2 116.1 . . ?
C6 N2 C2 127.7(3) . . ?
N1 C1 C1 115.7(3) . 3_766 ?
N1 C1 C2 119.1(3) . . ?
C2 C1 C1 125.1(3) . 3_766 ?
C7 C8 P1 119.9(2) . . ?
C9 C8 P1 122.5(2) . . ?
C9 C8 C7 117.5(3) . . ?
N2 C2 C1 119.7(3) . . ?
C3 C2 N2 122.0(3) . . ?
C3 C2 C1 118.3(3) . . ?
C20 C19 P1 125.3(3) . . ?
C20 C19 C24 117.9(3) . . ?
C24 C19 P1 116.8(3) . . ?
C8 C7 C6 119.6(3) . . ?
C12 C7 C8 120.2(3) . . ?
C12 C7 C6 120.1(3) . . ?
O1 C6 N2 125.7(3) . . ?
O1 C6 C7 121.5(3) . . ?
N2 C6 C7 112.8(3) . . ?
N1 C5 H5 118.7 . . ?
N1 C5 C4 122.7(3) . . ?
C4 C5 H5 118.7 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.3(3) . . ?
C10 C9 H9 118.8 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.5 . . ?
C14 C13 P1 124.9(3) . . ?
C14 C13 C18 117.8(3) . . ?
C18 C13 P1 117.1(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 121.1(3) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.3(4) . . ?
C17 C18 H18 119.3 . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C16 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 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
P1 C8 1.841(3) . ?
P1 C19 1.830(3) . ?
P1 C13 1.831(3) . ?
O1 C6 1.220(4) . ?
N1 C1 1.348(4) . ?
N1 C5 1.330(4) . ?
N2 H2 0.8800 . ?
N2 C2 1.401(4) . ?
N2 C6 1.366(4) . ?
C1 C1 1.497(6) 3_766 ?
C1 C2 1.421(4) . ?
C8 C7 1.410(4) . ?
C8 C9 1.391(4) . ?
C2 C3 1.385(5) . ?
C19 C20 1.386(5) . ?
C19 C24 1.388(5) . ?
C7 C6 1.506(4) . ?
C7 C12 1.384(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.366(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C13 C14 1.389(5) . ?
C13 C18 1.413(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.374(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.397(5) . ?
C4 H4 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.367(6) . ?
C24 H24 0.9500 . ?
C24 C23 1.383(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.356(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.378(6) . ?
C16 H16 0.9500 . ?
C16 C15 1.374(6) . ?
C15 H15 0.9500 . ?
C23 H23 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C7 C6 4.6(4) . . . . ?
P1 C8 C7 C12 -179.2(2) . . . . ?
P1 C8 C9 C10 178.2(3) . . . . ?
P1 C19 C20 C21 -178.6(2) . . . . ?
P1 C19 C24 C23 178.2(3) . . . . ?
P1 C13 C14 C15 174.4(3) . . . . ?
P1 C13 C18 C17 -175.2(3) . . . . ?
N1 C1 C2 N2 -177.3(3) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
N1 C5 C4 C3 1.1(6) . . . . ?
N2 C2 C3 C4 176.6(3) . . . . ?
C1 N1 C5 C4 -1.8(5) . . . . ?
C1 C1 C2 N2 0.5(6) 3_766 . . . ?
C1 C1 C2 C3 179.2(4) 3_766 . . . ?
C1 C2 C3 C4 -2.1(5) . . . . ?
C8 P1 C19 C20 -15.3(3) . . . . ?
C8 P1 C19 C24 164.6(3) . . . . ?
C8 P1 C13 C14 112.2(3) . . . . ?
C8 P1 C13 C18 -73.4(3) . . . . ?
C8 C7 C6 O1 36.0(5) . . . . ?
C8 C7 C6 N2 -144.3(3) . . . . ?
C8 C7 C12 C11 1.6(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C2 N2 C6 O1 8.9(6) . . . . ?
C2 N2 C6 C7 -170.8(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C19 P1 C8 C7 -97.6(3) . . . . ?
C19 P1 C8 C9 86.1(3) . . . . ?
C19 P1 C13 C14 7.0(3) . . . . ?
C19 P1 C13 C18 -178.6(3) . . . . ?
C19 C20 C21 C22 -0.9(5) . . . . ?
C19 C24 C23 C22 1.7(6) . . . . ?
C7 C8 C9 C10 1.8(5) . . . . ?
C6 N2 C2 C1 -178.9(3) . . . . ?
C6 N2 C2 C3 2.5(5) . . . . ?
C6 C7 C12 C11 177.8(3) . . . . ?
C5 N1 C1 C1 -177.5(3) . . . 3_766 ?
C5 N1 C1 C2 0.5(5) . . . . ?
C9 C8 C7 C6 -178.9(3) . . . . ?
C9 C8 C7 C12 -2.7(5) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C20 C19 C24 C23 -1.9(5) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C13 P1 C8 C7 156.9(3) . . . . ?
C13 P1 C8 C9 -19.4(3) . . . . ?
C13 P1 C19 C20 89.2(3) . . . . ?
C13 P1 C19 C24 -91.0(3) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C13 C18 C17 C16 0.5(6) . . . . ?
C21 C22 C23 C24 -1.0(6) . . . . ?
C12 C7 C6 O1 -140.3(3) . . . . ?
C12 C7 C6 N2 39.4(4) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C24 C19 C20 C21 1.5(5) . . . . ?
C18 C13 C14 C15 0.1(5) . . . . ?
C18 C17 C16 C15 -0.3(6) . . . . ?
C17 C16 C15 C14 0.0(6) . . . . ?
