#------------------------------------------------------------------------------
#$Date: 2024-12-05 22:09:13 +0200 (Thu, 05 Dec 2024) $
#$Revision: 296231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160279.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_7160279
loop_
_publ_author_name
'Kukreti, Prashant'
'Chauhan, Rahul'
'Panwar, Abhishek'
'Ghosh, Kaushik'
_publ_section_title
;
 A multi-component synthetic route for 2-pyrazolines via
 acceptorless dehydrogenation of alcohols using homogeneous Ni(II)
 catalysts.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8273
_journal_page_last               8278
_journal_paper_doi               10.1039/d4ob01352b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C12.5 H14.5 Cl N2.5 Ni0.5'
_chemical_formula_sum            'C12.5 H14.5 Cl N2.5 Ni0.5'
_chemical_formula_weight         264.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-06
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.8650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.0346(10)
_cell_length_b                   9.1005(4)
_cell_length_c                   14.6912(6)
_cell_measurement_reflns_used    9080
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      28.332
_cell_measurement_theta_min      2.474
_cell_volume                     2580.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      101.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54316
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.111
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.9429. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic yellowish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0341
_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)+(0.0217P)²+8.0638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3025
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01352b2.cif
_cod_data_source_block           kg_pk_584_0297_0m_a
_cod_original_formula_sum        'C12.50 H14.50 Cl N2.50 Ni0.50'
_cod_database_code               7160279
_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   0.955
_shelx_estimated_absorpt_t_min   0.834
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Ni1 Ni 0.500000 0.45150(3) 0.750000 0.01187(10) Uani 1 2 d S T P . .
Cl1 Cl 0.58114(2) 0.56707(5) 0.72310(3) 0.01730(11) Uani 1 1 d . . . . .
N1 N 0.42410(8) 0.24765(17) 0.57424(12) 0.0146(3) Uani 1 1 d . . . . .
N2 N 0.500000 0.2357(2) 0.750000 0.0129(4) Uani 1 2 d S T P . .
N3 N 0.42980(8) 0.40021(17) 0.58922(12) 0.0128(3) Uani 1 1 d . . . . .
C1 C 0.37205(10) 0.1823(2) 0.47927(14) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.38636(12) 0.1524(2) 0.39937(15) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.430334 0.175908 0.406038 0.026 Uiso 1 1 calc R . . . .
C3 C 0.33511(14) 0.0872(3) 0.30856(17) 0.0317(5) Uani 1 1 d . . . . .
H3 H 0.344132 0.065503 0.252951 0.038 Uiso 1 1 calc R . . . .
C4 C 0.27101(14) 0.0540(3) 0.29979(17) 0.0348(6) Uani 1 1 d . . . . .
H4 H 0.236345 0.009499 0.237977 0.042 Uiso 1 1 calc R . . . .
C5 C 0.25705(12) 0.0849(3) 0.37957(19) 0.0324(5) Uani 1 1 d . . . . .
H5 H 0.212918 0.062336 0.372620 0.039 Uiso 1 1 calc R . . . .
C6 C 0.30786(11) 0.1494(2) 0.47044(17) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.298720 0.170675 0.525985 0.027 Uiso 1 1 calc R . . . .
C7 C 0.46120(9) 0.1621(2) 0.66145(14) 0.0142(3) Uani 1 1 d . . . . .
C8 C 0.39534(10) 0.4836(2) 0.51061(14) 0.0145(3) Uani 1 1 d . . . . .
H8 H 0.367633 0.440331 0.444314 0.017 Uiso 1 1 calc R . . . .
C9 C 0.39753(10) 0.6475(2) 0.52037(14) 0.0141(3) Uani 1 1 d . . . . .
H9 H 0.433038 0.675246 0.592578 0.017 Uiso 1 1 calc R . . . .
C10 C 0.41764(11) 0.7150(2) 0.44327(16) 0.0210(4) Uani 1 1 d . . . . .
H10A H 0.419562 0.822223 0.450422 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.383065 0.688186 0.372287 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.463180 0.677892 0.457711 0.031 Uiso 1 1 calc GR . . . .
C11 C 0.45950(11) 0.0089(2) 0.65787(15) 0.0191(4) Uani 1 1 d . . . . .
H11 H 0.431687 -0.042220 0.594775 0.023 Uiso 1 1 calc R . . . .
C12 C 0.500000 -0.0661(3) 0.750000 0.0204(6) Uani 1 2 d S T P . .
H12 H 0.500003 -0.170539 0.749999 0.025 Uiso 1 2 calc RS T P . .
C13 C 0.32634(11) 0.7024(2) 0.50026(17) 0.0220(4) Uani 1 1 d . . . . .
H13A H 0.326182 0.810038 0.501207 0.033 Uiso 1 1 calc GR . . . .
H13B H 0.316681 0.664828 0.554487 0.033 Uiso 1 1 calc GR . . . .
H13C H 0.290642 0.667318 0.432222 0.033 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'
Cl Cl 0.1484 0.1585 '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'
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
Cl1 Ni1 Cl1 124.73(3) 2_656 . ?
N2 Ni1 Cl1 117.636(14) . . ?
N2 Ni1 Cl1 117.636(14) . 2_656 ?
N2 Ni1 N3 77.52(4) . 2_656 ?
N2 Ni1 N3 77.52(4) . . ?
N3 Ni1 Cl1 96.80(4) . . ?
N3 Ni1 Cl1 96.80(4) 2_656 2_656 ?
N3 Ni1 Cl1 94.71(4) . 2_656 ?
N3 Ni1 Cl1 94.71(4) 2_656 . ?
N3 Ni1 N3 155.03(8) . 2_656 ?
N3 N1 C1 122.05(15) . . ?
C7 N1 N3 116.40(15) . . ?
C7 N1 C1 120.31(15) . . ?
C7 N2 Ni1 119.95(11) . . ?
C7 N2 Ni1 119.96(11) 2_656 . ?
C7 N2 C7 120.1(2) 2_656 . ?
N1 N3 Ni1 110.39(11) . . ?
C8 N3 Ni1 131.16(13) . . ?
C8 N3 N1 118.45(15) . . ?
C2 C1 N1 120.21(18) . . ?
C2 C1 C6 121.19(18) . . ?
C6 C1 N1 118.59(18) . . ?
C1 C2 C3 119.0(2) . . ?
C4 C3 C2 119.9(2) . . ?
C5 C4 C3 120.8(2) . . ?
C4 C5 C6 119.7(2) . . ?
C1 C6 C5 119.5(2) . . ?
N1 C7 C11 122.38(17) . . ?
N2 C7 N1 115.71(17) . . ?
N2 C7 C11 121.91(17) . . ?
N3 C8 C9 121.78(16) . . ?
C8 C9 C10 109.68(15) . . ?
C8 C9 C13 108.87(16) . . ?
C10 C9 C13 111.19(16) . . ?
C12 C11 C7 117.50(18) . . ?
C11 C12 C11 121.1(3) . 2_656 ?
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 Cl1 2.2674(5) 2_656 ?
Ni1 Cl1 2.2674(5) . ?
Ni1 N2 1.964(2) . ?
Ni1 N3 2.1593(15) 2_656 ?
Ni1 N3 2.1593(15) . ?
N1 N3 1.402(2) . ?
N1 C1 1.439(2) . ?
N1 C7 1.380(2) . ?
N2 C7 1.341(2) 2_656 ?
N2 C7 1.341(2) . ?
N3 C8 1.281(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.388(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.392(3) . ?
C7 C11 1.396(3) . ?
C8 C9 1.497(3) . ?
C9 C10 1.530(3) . ?
C9 C13 1.533(3) . ?
C11 C12 1.389(2) . ?
