#------------------------------------------------------------------------------
#$Date: 2021-04-04 12:58:41 +0300 (Sun, 04 Apr 2021) $
#$Revision: 263584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518566.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_4518566
loop_
_publ_author_name
'Li, Huaifeng'
'Lupp, Daniel'
'Das, Pradip K.'
'Yang, Li'
'Gonçalves, Théo P.'
'Huang, Mei-Hui'
'El Hajoui, Marwa'
'Liang, Lan-Chang'
'Huang, Kuo-Wei'
_publ_section_title
;
 Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative
 to the Staudinger/Aza-Wittig Reaction
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4071
_journal_page_last               4076
_journal_paper_doi               10.1021/acscatal.1c00379
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H25 Cl N3 Ni P'
_chemical_formula_sum            'C18 H25 Cl N3 Ni P'
_chemical_formula_weight         408.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 118.179(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1382(15)
_cell_length_b                   8.1442(8)
_cell_length_c                   16.0627(18)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.54
_cell_volume                     1860.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (?, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      119.99
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.867
_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  0.0986
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51312
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.926
_diffrn_reflns_theta_min         2.537
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.0972 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       Block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0407
_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)+(0.0350P)²+2.0596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00379_si_005.cif
_cod_data_source_block           kkk_a
_cod_depositor_comments
'Adding full bibliography for 4518564--4518568.cif.'
_cod_database_code               4518566
_shelx_shelxl_version_number     2016/6
_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   0.803
_shelx_estimated_absorpt_t_min   0.766
_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:
 C7(H7), C10(H10), C2(H2), C4(H4), C9(H9), C8(H8), C3(H3)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.69116(3) 0.54943(4) 0.74242(3) 0.01552(12) Uani 1 1 d . . . . .
P1 P 0.79313(5) 0.72326(9) 0.83943(6) 0.01387(17) Uani 1 1 d . . . . .
Cl1 Cl 0.58908(6) 0.56884(12) 0.79278(7) 0.0387(3) Uani 1 1 d . . . . .
N3 N 0.61869(18) 0.3980(3) 0.63655(19) 0.0177(5) Uani 1 1 d . . . . .
N2 N 0.78315(17) 0.5141(3) 0.70646(18) 0.0146(5) Uani 1 1 d . . . . .
N1 N 0.88557(17) 0.6994(3) 0.82045(19) 0.0177(5) Uani 1 1 d . . . . .
C6 C 0.6668(2) 0.3487(3) 0.5906(2) 0.0175(6) Uani 1 1 d . . . . .
C5 C 0.7650(2) 0.4037(3) 0.6363(2) 0.0162(6) Uani 1 1 d . . . . .
C7 C 0.6245(2) 0.2549(4) 0.5085(2) 0.0241(7) Uani 1 1 d . . . . .
H7 H 0.659008 0.223132 0.476858 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5287(2) 0.3499(4) 0.6027(3) 0.0266(7) Uani 1 1 d . . . . .
H10 H 0.494932 0.382328 0.634945 0.032 Uiso 1 1 calc R . . . .
C1 C 0.8708(2) 0.5876(3) 0.7554(2) 0.0164(6) Uani 1 1 d . . . . .
C2 C 0.9427(2) 0.5316(4) 0.7336(2) 0.0200(6) Uani 1 1 d . . . . .
H2 H 1.004172 0.576321 0.766850 0.024 Uiso 1 1 calc R . . . .
C11 C 0.7550(2) 0.9406(4) 0.8081(2) 0.0208(6) Uani 1 1 d . . . . .
C4 C 0.8329(2) 0.3509(4) 0.6147(2) 0.0215(7) Uani 1 1 d . . . . .
H4 H 0.818911 0.272455 0.566111 0.026 Uiso 1 1 calc R . . . .
C9 C 0.4839(3) 0.2544(5) 0.5221(3) 0.0323(8) Uani 1 1 d . . . . .
H9 H 0.420594 0.220915 0.500253 0.039 Uiso 1 1 calc R . . . .
C15 C 0.8430(2) 0.6754(4) 0.9673(2) 0.0223(7) Uani 1 1 d . . . . .
C13 C 0.8346(3) 1.0622(4) 0.8595(3) 0.0348(9) Uani 1 1 d . . . . .
H13A H 0.814021 1.172152 0.832898 0.052 Uiso 1 1 calc GR . . . .
H13B H 0.889118 1.029501 0.852045 0.052 Uiso 1 1 calc GR . . . .
H13C H 0.851829 1.063413 0.926766 0.052 Uiso 1 1 calc GR . . . .
C8 C 0.5314(3) 0.2084(4) 0.4737(3) 0.0301(8) Uani 1 1 d . . . . .
H8 H 0.500764 0.145703 0.417363 0.036 Uiso 1 1 calc R . . . .
C3 C 0.9242(2) 0.4156(4) 0.6662(3) 0.0234(7) Uani 1 1 d . . . . .
H3 H 0.973077 0.378082 0.653874 0.028 Uiso 1 1 calc R . . . .
C17 C 0.9381(2) 0.7618(4) 1.0241(2) 0.0271(7) Uani 1 1 d . . . . .
H17A H 0.927996 0.880316 1.025161 0.041 Uiso 1 1 calc GR . . . .
H17B H 0.978085 0.740786 0.994580 0.041 Uiso 1 1 calc GR . . . .
H17C H 0.968898 0.719533 1.088932 0.041 Uiso 1 1 calc GR . . . .
C14 C 0.6715(3) 0.9848(5) 0.8238(4) 0.0542(14) Uani 1 1 d . . . . .
H14A H 0.691814 0.988054 0.891684 0.081 Uiso 1 1 calc GR . . . .
H14B H 0.622084 0.902039 0.793711 0.081 Uiso 1 1 calc GR . . . .
H14C H 0.647081 1.092697 0.796018 0.081 Uiso 1 1 calc GR . . . .
C16 C 0.8609(3) 0.4891(5) 0.9722(3) 0.0402(9) Uani 1 1 d . . . . .
H16A H 0.896320 0.455103 1.038423 0.060 Uiso 1 1 calc GR . . . .
H16B H 0.897124 0.462760 0.939252 0.060 Uiso 1 1 calc GR . . . .
H16C H 0.800639 0.430863 0.942088 0.060 Uiso 1 1 calc GR . . . .
C18 C 0.7784(3) 0.7162(6) 1.0093(3) 0.0443(11) Uani 1 1 d . . . . .
H18A H 0.806857 0.677290 1.074713 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.717555 0.662195 0.972238 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.769288 0.835304 1.007894 0.066 Uiso 1 1 calc GR . . . .
C12 C 0.7242(4) 0.9495(5) 0.7026(3) 0.0464(11) Uani 1 1 d . . . . .
H12A H 0.695192 1.056592 0.678058 0.070 Uiso 1 1 calc GR . . . .
H12B H 0.678509 0.862267 0.669678 0.070 Uiso 1 1 calc GR . . . .
H12C H 0.779032 0.935519 0.692444 0.070 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'
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
Cl1 Ni1 P1 97.89(3) . . ?
N3 Ni1 P1 164.67(7) . . ?
N3 Ni1 Cl1 97.01(7) . . ?
N2 Ni1 P1 82.97(8) . . ?
N2 Ni1 Cl1 174.31(8) . . ?
N2 Ni1 N3 82.56(10) . . ?
N1 P1 Ni1 103.47(9) . . ?
N1 P1 C11 105.69(13) . . ?
N1 P1 C15 102.68(14) . . ?
C11 P1 Ni1 112.56(11) . . ?
C15 P1 Ni1 116.23(10) . . ?
C15 P1 C11 114.39(15) . . ?
C6 N3 Ni1 113.18(19) . . ?
C10 N3 Ni1 128.1(2) . . ?
C10 N3 C6 118.6(3) . . ?
C5 N2 Ni1 118.0(2) . . ?
C5 N2 C1 121.1(2) . . ?
C1 N2 Ni1 120.61(19) . . ?
C1 N1 P1 112.4(2) . . ?
N3 C6 C5 113.4(3) . . ?
N3 C6 C7 121.7(3) . . ?
C7 C6 C5 124.9(3) . . ?
N2 C5 C6 112.0(2) . . ?
N2 C5 C4 122.2(3) . . ?
C4 C5 C6 125.7(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
N3 C10 H10 119.0 . . ?
N3 C10 C9 121.9(3) . . ?
C9 C10 H10 119.0 . . ?
N2 C1 C2 116.8(3) . . ?
N1 C1 N2 120.0(2) . . ?
N1 C1 C2 123.2(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.5 . . ?
C13 C11 P1 112.7(2) . . ?
C13 C11 C14 110.0(3) . . ?
C13 C11 C12 108.8(3) . . ?
C14 C11 P1 112.6(2) . . ?
C12 C11 P1 103.8(2) . . ?
C12 C11 C14 108.8(4) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C17 C15 P1 110.5(2) . . ?
C17 C15 C16 108.1(3) . . ?
C16 C15 P1 103.6(2) . . ?
C18 C15 P1 114.5(3) . . ?
C18 C15 C17 109.7(3) . . ?
C18 C15 C16 110.1(3) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 P1 2.1722(9) . ?
Ni1 Cl1 2.1569(8) . ?
Ni1 N3 1.976(3) . ?
Ni1 N2 1.852(2) . ?
P1 N1 1.669(2) . ?
P1 C11 1.864(3) . ?
P1 C15 1.859(3) . ?
N3 C6 1.360(4) . ?
N3 C10 1.346(4) . ?
N2 C5 1.362(4) . ?
N2 C1 1.387(4) . ?
N1 C1 1.321(4) . ?
C6 C5 1.467(4) . ?
C6 C7 1.392(4) . ?
C5 C4 1.366(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.385(5) . ?
C1 C2 1.435(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.359(5) . ?
C11 C13 1.520(5) . ?
C11 C14 1.526(5) . ?
C11 C12 1.525(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.407(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.375(5) . ?
C15 C17 1.537(5) . ?
C15 C16 1.540(5) . ?
C15 C18 1.521(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
