#------------------------------------------------------------------------------
#$Date: 2021-04-04 12:58:41 +0300 (Sun, 04 Apr 2021) $
#$Revision: 263584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518564.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_4518564
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            'C22 H30 Cl2 N3 Ni P'
_chemical_formula_weight         497.07
_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                 105.394(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7864(9)
_cell_length_b                   12.0598(8)
_cell_length_c                   16.8359(12)
_cell_measurement_reflns_used    9562
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.97
_cell_volume                     2307.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            151725
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    1.156
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_refine_diff_density_max         1.308
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         7055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0379
_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)+(0.1700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.2046
_reflns_number_gt                6085
_reflns_number_total             7055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c00379_si_003.cif
_cod_data_source_block           new2
_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               4518564
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 0.54457(2) 0.82688(2) 0.769992(14) 0.01644(12) Uani 1 1 d . . .
P1 P 0.37082(4) 0.82274(4) 0.78386(3) 0.01625(14) Uani 1 1 d . . .
Cl2 Cl 0.17676(5) 0.60871(4) 0.88995(4) 0.02782(15) Uani 1 1 d . . .
Cl1 Cl 0.49229(4) 0.93842(4) 0.66835(3) 0.02457(15) Uani 1 1 d . . .
N3 N 0.71103(15) 0.81797(13) 0.77644(11) 0.0185(3) Uani 1 1 d . . .
C20 C 0.2860(3) 1.1083(2) 0.94190(17) 0.0409(6) Uani 1 1 d . . .
H34A H 0.2632 1.1819 0.9587 0.049 Uiso 1 1 calc R . .
H34B H 0.3074 1.0605 0.9915 0.049 Uiso 1 1 calc R . .
N1 N 0.39201(15) 0.73906(14) 0.86771(10) 0.0199(3) Uani 1 1 d . . .
N2 N 0.58312(14) 0.73208(13) 0.85910(10) 0.0175(3) Uani 1 1 d . . .
C6 C 0.76969(17) 0.74359(16) 0.83479(12) 0.0199(4) Uani 1 1 d . . .
C5 C 0.69649(17) 0.69602(17) 0.88421(12) 0.0189(3) Uani 1 1 d . . .
C1 C 0.50365(17) 0.70053(16) 0.89921(11) 0.0173(3) Uani 1 1 d . . .
C17 C 0.32327(17) 0.95623(17) 0.81440(12) 0.0213(4) Uani 1 1 d . . .
H6 H 0.3027 1.0049 0.7645 0.026 Uiso 1 1 calc R . .
C3 C 0.65105(19) 0.59476(16) 0.99359(12) 0.0222(4) Uani 1 1 d . . .
H7 H 0.6747 0.5475 1.0402 0.027 Uiso 1 1 calc R . .
C11 C 0.24905(17) 0.75898(16) 0.70761(12) 0.0196(3) Uani 1 1 d . . .
H8 H 0.1890 0.7372 0.7369 0.024 Uiso 1 1 calc R . .
C2 C 0.53697(19) 0.63287(16) 0.96931(12) 0.0209(4) Uani 1 1 d . . .
H9 H 0.4820 0.6138 0.9994 0.025 Uiso 1 1 calc R . .
C4 C 0.73219(19) 0.62482(16) 0.95035(12) 0.0222(4) Uani 1 1 d . . .
H10 H 0.8103 0.5969 0.9661 0.027 Uiso 1 1 calc R . .
C10 C 0.76943(18) 0.87184(17) 0.73076(13) 0.0230(4) Uani 1 1 d . . .
H11 H 0.7283 0.9241 0.6913 0.028 Uiso 1 1 calc R . .
C7 C 0.88797(18) 0.72109(18) 0.84419(14) 0.0262(4) Uani 1 1 d . . .
H13 H 0.9278 0.6682 0.8837 0.031 Uiso 1 1 calc R . .
C18 C 0.2141(2) 0.94603(18) 0.84652(15) 0.0269(4) Uani 1 1 d . . .
H14A H 0.1475 0.9187 0.8017 0.032 Uiso 1 1 calc R . .
H14B H 0.2293 0.8910 0.8918 0.032 Uiso 1 1 calc R . .
C21 C 0.3912(3) 1.12091(19) 0.90732(16) 0.0336(5) Uani 1 1 d . . .
H15A H 0.4582 1.1516 0.9503 0.040 Uiso 1 1 calc R . .
H15B H 0.3720 1.1738 0.8607 0.040 Uiso 1 1 calc R . .
C9 C 0.88841(19) 0.8544(2) 0.73865(15) 0.0283(4) Uani 1 1 d . . .
H17 H 0.9285 0.8949 0.7060 0.034 Uiso 1 1 calc R . .
C22 C 0.42663(19) 1.01045(17) 0.87795(13) 0.0254(4) Uani 1 1 d . . .
H19A H 0.4539 0.9602 0.9257 0.031 Uiso 1 1 calc R . .
H19B H 0.4928 1.0220 0.8529 0.031 Uiso 1 1 calc R . .
C19 C 0.1807(2) 1.0567(2) 0.87797(18) 0.0374(6) Uani 1 1 d . . .
H22A H 0.1149 1.0453 0.9034 0.045 Uiso 1 1 calc R . .
H22B H 0.1536 1.1084 0.8311 0.045 Uiso 1 1 calc R . .
C8 C 0.94731(19) 0.7765(2) 0.79538(16) 0.0297(4) Uani 1 1 d . . .
H23 H 1.0281 0.7613 0.8007 0.036 Uiso 1 1 calc R . .
C16 C 0.1877(2) 0.83633(18) 0.63714(14) 0.0266(4) Uani 1 1 d . . .
H55A H 0.2441 0.8595 0.6060 0.032 Uiso 1 1 calc R . .
H55B H 0.1597 0.9036 0.6599 0.032 Uiso 1 1 calc R . .
C12 C 0.2899(2) 0.65212(19) 0.67452(14) 0.0280(4) Uani 1 1 d . . .
H51A H 0.3275 0.6026 0.7209 0.034 Uiso 1 1 calc R . .
H51B H 0.3487 0.6699 0.6440 0.034 Uiso 1 1 calc R . .
C15 C 0.0831(2) 0.7766(2) 0.57939(15) 0.0344(5) Uani 1 1 d . . .
H54A H 0.0231 0.7607 0.6093 0.041 Uiso 1 1 calc R . .
H54B H 0.0469 0.8256 0.5323 0.041 Uiso 1 1 calc R . .
C13 C 0.1838(3) 0.5935(2) 0.61709(16) 0.0373(5) Uani 1 1 d . . .
H52A H 0.2108 0.5261 0.5940 0.045 Uiso 1 1 calc R . .
H52B H 0.1285 0.5703 0.6491 0.045 Uiso 1 1 calc R . .
C14 C 0.1205(3) 0.6691(2) 0.54731(16) 0.0402(6) Uani 1 1 d . . .
H53A H 0.1732 0.6857 0.5118 0.048 Uiso 1 1 calc R . .
H53B H 0.0502 0.6305 0.5132 0.048 Uiso 1 1 calc R . .
H1 H 0.327(3) 0.706(3) 0.879(2) 0.033(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 83.86(7) . . ?
N2 Ni1 P1 86.13(5) . . ?
N3 Ni1 P1 169.76(6) . . ?
N2 Ni1 Cl1 177.26(5) . . ?
N3 Ni1 Cl1 98.76(5) . . ?
P1 Ni1 Cl1 91.23(2) . . ?
N1 P1 C11 104.43(9) . . ?
N1 P1 C17 106.17(9) . . ?
C11 P1 C17 109.13(9) . . ?
N1 P1 Ni1 99.91(6) . . ?
C11 P1 Ni1 122.34(7) . . ?
C17 P1 Ni1 112.84(7) . . ?
C10 N3 C6 119.54(18) . . ?
C10 N3 Ni1 127.73(14) . . ?
C6 N3 Ni1 112.70(14) . . ?
C21 C20 C19 111.3(2) . . ?
C1 N1 P1 116.08(14) . . ?
C1 N2 C5 120.66(17) . . ?
C1 N2 Ni1 121.93(13) . . ?
C5 N2 Ni1 117.39(13) . . ?
N3 C6 C7 120.59(19) . . ?
N3 C6 C5 113.66(17) . . ?
C7 C6 C5 125.73(18) . . ?
N2 C5 C4 120.87(19) . . ?
N2 C5 C6 112.09(17) . . ?
C4 C5 C6 127.03(18) . . ?
N2 C1 N1 115.89(16) . . ?
N2 C1 C2 120.64(18) . . ?
N1 C1 C2 123.47(18) . . ?
C18 C17 C22 111.97(17) . . ?
C18 C17 P1 112.32(14) . . ?
C22 C17 P1 109.01(14) . . ?
C2 C3 C4 120.62(18) . . ?
C12 C11 C16 111.11(17) . . ?
C12 C11 P1 110.27(14) . . ?
C16 C11 P1 114.23(14) . . ?
C3 C2 C1 118.52(19) . . ?
C5 C4 C3 118.57(19) . . ?
N3 C10 C9 122.4(2) . . ?
C8 C7 C6 119.2(2) . . ?
C19 C18 C17 111.8(2) . . ?
C20 C21 C22 111.2(2) . . ?
C8 C9 C10 118.5(2) . . ?
C21 C22 C17 111.38(19) . . ?
C18 C19 C20 111.1(2) . . ?
C7 C8 C9 119.8(2) . . ?
C11 C16 C15 109.90(18) . . ?
C11 C12 C13 109.51(19) . . ?
C14 C15 C16 111.6(2) . . ?
C14 C13 C12 111.2(2) . . ?
C15 C14 C13 111.6(2) . . ?
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 1.8446(16) . ?
Ni1 N3 1.9390(18) . ?
Ni1 P1 2.1224(6) . ?
Ni1 Cl1 2.1348(5) . ?
P1 N1 1.6990(17) . ?
P1 C11 1.822(2) . ?
P1 C17 1.823(2) . ?
N3 C10 1.330(3) . ?
N3 C6 1.374(2) . ?
C20 C21 1.511(4) . ?
C20 C19 1.542(4) . ?
N1 C1 1.363(2) . ?
N2 C1 1.347(2) . ?
N2 C5 1.361(2) . ?
C6 C7 1.387(3) . ?
C6 C5 1.465(3) . ?
C5 C4 1.380(3) . ?
C1 C2 1.402(3) . ?
C17 C18 1.527(3) . ?
C17 C22 1.538(3) . ?
C3 C2 1.376(3) . ?
C3 C4 1.395(3) . ?
C11 C12 1.532(3) . ?
C11 C16 1.532(3) . ?
C10 C9 1.389(3) . ?
C7 C8 1.384(3) . ?
C18 C19 1.526(3) . ?
C21 C22 1.517(3) . ?
C9 C8 1.387(3) . ?
C16 C15 1.532(3) . ?
C12 C13 1.535(3) . ?
C15 C14 1.515(4) . ?
C13 C14 1.517(4) . ?
