#------------------------------------------------------------------------------
#$Date: 2021-04-04 12:58:41 +0300 (Sun, 04 Apr 2021) $
#$Revision: 263584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518568.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_4518568
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_sum            'C18 H26 Cl2 N3 Ni P'
_chemical_formula_weight         445.00
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.400(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1286(8)
_cell_length_b                   12.4385(8)
_cell_length_c                   13.4746(9)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    136(2)
_cell_measurement_theta_max      34.20
_cell_measurement_theta_min      2.35
_cell_volume                     2023.8(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      136(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_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            51756
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    1.308
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                3476
_reflns_number_total             3982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c00379_si_002.cif
_cod_data_source_block           newa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518564--4518568.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4518568
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.72585(2) 0.68785(2) 0.33561(3) 0.02105(18) Uani 1 1 d . . .
Cl1 Cl 0.62207(6) 0.70013(5) 0.45911(7) 0.0380(2) Uani 1 1 d . . .
Cl2 Cl 0.88839(6) 0.29086(5) 0.14256(6) 0.0306(2) Uani 1 1 d . . .
P1 P 0.70288(5) 0.51739(5) 0.30904(5) 0.0208(2) Uani 1 1 d . . .
N1 N 0.78260(18) 0.49729(18) 0.21008(19) 0.0254(5) Uani 1 1 d . . .
N2 N 0.81609(16) 0.67763(16) 0.22882(17) 0.0183(5) Uani 1 1 d . . .
N3 N 0.76243(17) 0.83982(18) 0.33433(17) 0.0236(5) Uani 1 1 d . . .
C1 C 0.83535(19) 0.5840(2) 0.18029(19) 0.0201(5) Uani 1 1 d . . .
C2 C 0.9058(2) 0.5790(2) 0.10199(19) 0.0246(6) Uani 1 1 d . . .
H6 H 0.9209 0.5126 0.0712 0.030 Uiso 1 1 calc R . .
C3 C 0.9506(2) 0.6717(2) 0.0729(2) 0.0281(6) Uani 1 1 d . . .
H16 H 0.9968 0.6719 0.0196 0.034 Uiso 1 1 calc R . .
C4 C 0.9284(2) 0.7694(2) 0.1224(2) 0.0282(6) Uani 1 1 d . . .
H17 H 0.9592 0.8348 0.1014 0.034 Uiso 1 1 calc R . .
C5 C 0.86192(19) 0.7698(2) 0.2014(2) 0.0221(5) Uani 1 1 d . . .
C6 C 0.83159(19) 0.8632(2) 0.2632(2) 0.0233(6) Uani 1 1 d . . .
C7 C 0.8681(2) 0.9660(2) 0.2528(2) 0.0296(6) Uani 1 1 d . . .
H18 H 0.9187 0.9821 0.2051 0.036 Uiso 1 1 calc R . .
C8 C 0.8302(2) 1.0489(2) 0.3136(2) 0.0330(7) Uani 1 1 d . . .
H19 H 0.8535 1.1210 0.3050 0.040 Uiso 1 1 calc R . .
C9 C 0.7599(2) 1.0252(2) 0.3846(2) 0.0315(6) Uani 1 1 d . . .
H2 H 0.7341 1.0797 0.4261 0.038 Uiso 1 1 calc R . .
C10 C 0.7280(2) 0.9195(2) 0.3938(2) 0.0274(6) Uani 1 1 d . . .
H40 H 0.6804 0.9015 0.4434 0.033 Uiso 1 1 calc R . .
C11 C 0.5791(2) 0.4805(2) 0.2374(2) 0.0299(6) Uani 1 1 d . . .
C12 C 0.5441(2) 0.5811(3) 0.1689(3) 0.0468(9) Uani 1 1 d . . .
H14A H 0.4740 0.5657 0.1292 0.070 Uiso 1 1 calc R . .
H14B H 0.6017 0.5956 0.1244 0.070 Uiso 1 1 calc R . .
H14C H 0.5349 0.6442 0.2110 0.070 Uiso 1 1 calc R . .
C13 C 0.5871(3) 0.3852(3) 0.1591(2) 0.0444(8) Uani 1 1 d . . .
H8A H 0.6136 0.3199 0.1943 0.067 Uiso 1 1 calc R . .
H8B H 0.6388 0.4053 0.1106 0.067 Uiso 1 1 calc R . .
H8C H 0.5137 0.3719 0.1243 0.067 Uiso 1 1 calc R . .
C14 C 0.7438(3) 0.3082(2) 0.3868(2) 0.0333(7) Uani 1 1 d . . .
H11A H 0.7788 0.3023 0.3243 0.050 Uiso 1 1 calc R . .
H11B H 0.6662 0.2857 0.3756 0.050 Uiso 1 1 calc R . .
H11C H 0.7829 0.2618 0.4374 0.050 Uiso 1 1 calc R . .
C15 C 0.8596(2) 0.4574(2) 0.4509(3) 0.0356(7) Uani 1 1 d . . .
H12A H 0.8919 0.4106 0.5045 0.053 Uiso 1 1 calc R . .
H12B H 0.8605 0.5320 0.4743 0.053 Uiso 1 1 calc R . .
H12C H 0.9029 0.4516 0.3933 0.053 Uiso 1 1 calc R . .
C16 C 0.74957(19) 0.4256(2) 0.4230(2) 0.0234(6) Uani 1 1 d . . .
C17 C 0.6939(2) 0.4393(2) 0.5267(2) 0.0292(6) Uani 1 1 d . . .
H13A H 0.7332 0.3939 0.5779 0.044 Uiso 1 1 calc R . .
H13B H 0.6160 0.4176 0.5171 0.044 Uiso 1 1 calc R . .
H13C H 0.6989 0.5147 0.5479 0.044 Uiso 1 1 calc R . .
C18 C 0.5035(2) 0.4565(3) 0.3213(2) 0.0428(8) Uani 1 1 d . . .
H9A H 0.5075 0.5165 0.3687 0.064 Uiso 1 1 calc R . .
H9B H 0.5283 0.3904 0.3560 0.064 Uiso 1 1 calc R . .
H9C H 0.4269 0.4477 0.2921 0.064 Uiso 1 1 calc R . .
H1 H 0.803(2) 0.431(3) 0.195(2) 0.024(7) Uiso 1 1 d . . .
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'
P P 0.1023 0.0942 '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'
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
N2 Ni1 N3 84.82(9) . . ?
N2 Ni1 P1 83.28(6) . . ?
N3 Ni1 P1 168.01(7) . . ?
N2 Ni1 Cl1 179.79(7) . . ?
N3 Ni1 Cl1 95.00(7) . . ?
P1 Ni1 Cl1 96.90(3) . . ?
N1 P1 C11 92.79(13) . . ?
N1 P1 C16 112.22(11) . . ?
C11 P1 C16 116.48(12) . . ?
N1 P1 Ni1 101.28(8) . . ?
C11 P1 Ni1 115.76(10) . . ?
C16 P1 Ni1 114.78(8) . . ?
C1 N1 P1 115.58(19) . . ?
C5 N2 C1 120.2(2) . . ?
C5 N2 Ni1 115.86(17) . . ?
C1 N2 Ni1 123.94(17) . . ?
C6 N3 C10 120.1(2) . . ?
C6 N3 Ni1 111.72(18) . . ?
C10 N3 Ni1 128.22(19) . . ?
N1 C1 N2 115.9(2) . . ?
N1 C1 C2 121.8(2) . . ?
N2 C1 C2 122.3(2) . . ?
C3 C2 C1 117.8(3) . . ?
C2 C3 C4 119.6(3) . . ?
C5 C4 C3 120.7(2) . . ?
N2 C5 C4 119.4(2) . . ?
N2 C5 C6 112.4(2) . . ?
C4 C5 C6 128.2(2) . . ?
N3 C6 C7 120.0(3) . . ?
N3 C6 C5 115.2(2) . . ?
C7 C6 C5 124.8(3) . . ?
C6 C7 C8 119.6(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C10 117.7(3) . . ?
N3 C10 C9 122.4(3) . . ?
C18 C11 C12 115.5(3) . . ?
C18 C11 C13 114.6(3) . . ?
C12 C11 C13 103.4(3) . . ?
C18 C11 P1 100.48(19) . . ?
C12 C11 P1 106.2(2) . . ?
C13 C11 P1 116.9(2) . . ?
C15 C16 C14 111.3(2) . . ?
C15 C16 C17 101.6(2) . . ?
C14 C16 C17 111.3(2) . . ?
C15 C16 P1 104.07(19) . . ?
C14 C16 P1 107.69(19) . . ?
C17 C16 P1 120.26(17) . . ?
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 N2 1.892(2) . ?
Ni1 N3 1.942(2) . ?
Ni1 P1 2.1639(7) . ?
Ni1 Cl1 2.1843(8) . ?
P1 N1 1.737(2) . ?
P1 C11 1.768(3) . ?
P1 C16 1.954(3) . ?
N1 C1 1.335(3) . ?
N2 C5 1.342(3) . ?
N2 C1 1.366(3) . ?
N3 C6 1.363(3) . ?
N3 C10 1.365(4) . ?
C1 C2 1.420(4) . ?
C2 C3 1.349(4) . ?
C3 C4 1.424(4) . ?
C4 C5 1.395(4) . ?
C5 C6 1.495(4) . ?
C6 C7 1.366(4) . ?
C7 C8 1.420(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.379(4) . ?
C11 C18 1.550(4) . ?
C11 C12 1.589(4) . ?
C11 C13 1.595(4) . ?
C14 C16 1.540(4) . ?
C15 C16 1.409(3) . ?
C16 C17 1.617(4) . ?
