#------------------------------------------------------------------------------
#$Date: 2021-06-20 03:49:49 +0300 (Sun, 20 Jun 2021) $
#$Revision: 266584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/35/1563596.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_1563596
loop_
_publ_author_name
'Min, Sehye'
'Choi, Jonghoon'
'Yoo, Changho'
'Graham, Peter M.'
'Lee, Yunho'
_publ_section_title
;
 Ni(0)-Promoted Activation of Csp2--H and Csp2--O Bonds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02210E
_journal_year                    2021
_chemical_formula_moiety         'C35 H49 N Ni P2'
_chemical_formula_sum            'C35 H49 N Ni P2'
_chemical_formula_weight         604.40
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-11-26 deposited with the CCDC.	2021-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2049(9)
_cell_length_b                   18.8750(11)
_cell_length_c                   10.0825(6)
_cell_measurement_reflns_used    35839
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.920
_cell_measurement_theta_min      2.368
_cell_volume                     3274.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35839
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.920
_diffrn_reflns_theta_min         2.368
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6232
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 2711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.015(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         7556
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0448
_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)+(0.0577P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                6622
_reflns_number_total             7556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02210e2.cif
_cod_data_source_block           0548A-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1563596
_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_min   0.763
_shelx_estimated_absorpt_t_max   0.923
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.52492(2) 0.23324(2) 0.59840(6) 0.01583(12) Uani 1 1 d . . . . .
P2 P 0.53401(5) 0.30940(5) 0.43885(10) 0.0166(2) Uani 1 1 d . . . . .
P1 P 0.50070(5) 0.16387(5) 0.76400(11) 0.0161(2) Uani 1 1 d . . . . .
N1 N 0.44558(18) 0.29458(16) 0.6711(3) 0.0166(6) Uani 1 1 d . . . . .
C1 C 0.40011(19) 0.27275(17) 0.7771(4) 0.0153(7) Uani 1 1 d . . . . .
C3 C 0.3655(2) 0.17631(19) 0.9284(4) 0.0193(8) Uani 1 1 d . . . . .
H3 H 0.3749 0.1298 0.9607 0.023 Uiso 1 1 calc R U . . .
C6 C 0.3390(2) 0.31409(19) 0.8315(4) 0.0166(8) Uani 1 1 d . . . . .
C2 C 0.4143(2) 0.2053(2) 0.8311(4) 0.0171(8) Uani 1 1 d . . . . .
C5 C 0.2930(2) 0.28388(19) 0.9303(4) 0.0198(8) Uani 1 1 d . . . . .
H5 H 0.2525 0.3117 0.9673 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3032(2) 0.2152(2) 0.9779(4) 0.0205(9) Uani 1 1 d . . . . .
C9 C 0.36392(19) 0.47237(18) 0.6005(5) 0.0216(8) Uani 1 1 d . . . . .
H9 H 0.3270 0.5047 0.6358 0.026 Uiso 1 1 calc R U . . .
C13 C 0.42880(19) 0.35978(17) 0.6142(4) 0.0159(7) Uani 1 1 d . . . . .
C11 C 0.4598(2) 0.44461(19) 0.4378(4) 0.0212(8) Uani 1 1 d . . . . .
H11 H 0.4896 0.4569 0.3619 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3729(2) 0.40763(19) 0.6638(4) 0.0177(8) Uani 1 1 d . . . . .
C7 C 0.3265(2) 0.39082(19) 0.7893(4) 0.0189(8) Uani 1 1 d . . . . .
C10 C 0.4056(2) 0.4930(2) 0.4882(4) 0.0208(8) Uani 1 1 d . . . . .
C12 C 0.47073(19) 0.3793(2) 0.4966(4) 0.0162(8) Uani 1 1 d . . . . .
C14 C 0.2483(2) 0.1839(2) 1.0802(5) 0.0286(10) Uani 1 1 d . . . . .
H14A H 0.2590 0.2049 1.1672 0.043 Uiso 1 1 calc R U . . .
H14B H 0.2559 0.1325 1.0846 0.043 Uiso 1 1 calc R U . . .
H14C H 0.1945 0.1941 1.0546 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3913(2) 0.5628(2) 0.4201(5) 0.0287(10) Uani 1 1 d . . . . .
H15A H 0.3505 0.5570 0.3531 0.043 Uiso 1 1 calc R U . . .
H15B H 0.4393 0.5788 0.3772 0.043 Uiso 1 1 calc R U . . .
H15C H 0.3747 0.5980 0.4857 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3536(3) 0.4397(2) 0.9020(4) 0.0316(10) Uani 1 1 d . . . . .
H16A H 0.3240 0.4290 0.9826 0.047 Uiso 1 1 calc R U . . .
H16B H 0.3450 0.4892 0.8766 0.047 Uiso 1 1 calc R U . . .
H16C H 0.4091 0.4319 0.9187 0.047 Uiso 1 1 calc R U . . .
C17 C 0.2383(2) 0.4033(2) 0.7632(5) 0.0300(10) Uani 1 1 d . . . . .
H17A H 0.2199 0.3695 0.6965 0.045 Uiso 1 1 calc R U . . .
H17B H 0.2304 0.4517 0.7309 0.045 Uiso 1 1 calc R U . . .
H17C H 0.2093 0.3965 0.8459 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5742(2) 0.16871(19) 0.8972(4) 0.0193(8) Uani 1 1 d . . . . .
H18 H 0.6208 0.1415 0.8671 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5992(2) 0.2455(2) 0.9175(5) 0.0261(9) Uani 1 1 d . . . . .
H20A H 0.5547 0.2735 0.9484 0.039 Uiso 1 1 calc R U . . .
H20B H 0.6181 0.2650 0.8333 0.039 Uiso 1 1 calc R U . . .
H20C H 0.6408 0.2475 0.9837 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5463(2) 0.1358(2) 1.0278(4) 0.0259(9) Uani 1 1 d . . . . .
H19A H 0.5871 0.1406 1.0951 0.039 Uiso 1 1 calc R U . . .
H19B H 0.5348 0.0855 1.0139 0.039 Uiso 1 1 calc R U . . .
H19C H 0.4993 0.1603 1.0579 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4776(2) 0.06872(19) 0.7444(5) 0.0201(8) Uani 1 1 d . . . . .
H21 H 0.4499 0.0529 0.8264 0.024 Uiso 1 1 calc R U . . .
C23 C 0.4215(2) 0.0609(2) 0.6279(5) 0.0293(10) Uani 1 1 d . . . . .
H23A H 0.4483 0.0732 0.5453 0.044 Uiso 1 1 calc R U . . .
H23B H 0.3771 0.0927 0.6406 0.044 Uiso 1 1 calc R U . . .
H23C H 0.4031 0.0119 0.6231 0.044 Uiso 1 1 calc R U . . .
C22 C 0.5498(2) 0.0223(2) 0.7281(4) 0.0257(10) Uani 1 1 d . . . . .
H22A H 0.5340 -0.0274 0.7197 0.038 Uiso 1 1 calc R U . . .
H22B H 0.5834 0.0278 0.8058 0.038 Uiso 1 1 calc R U . . .
H22C H 0.5781 0.0368 0.6482 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6267(2) 0.3529(2) 0.3963(4) 0.0212(8) Uani 1 1 d . . . . .
H24 H 0.6144 0.3962 0.3432 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6806(2) 0.3063(2) 0.3133(5) 0.0303(10) Uani 1 1 d . . . . .
H26A H 0.7294 0.3316 0.2967 0.046 Uiso 1 1 calc R U . . .
H26B H 0.6555 0.2951 0.2286 0.046 Uiso 1 1 calc R U . . .
H26C H 0.6916 0.2623 0.3614 0.046 Uiso 1 1 calc R U . . .
C25 C 0.6654(2) 0.3769(2) 0.5257(5) 0.0309(10) Uani 1 1 d . . . . .
H25A H 0.6795 0.3352 0.5785 0.046 Uiso 1 1 calc R U . . .
H25B H 0.6291 0.4065 0.5761 0.046 Uiso 1 1 calc R U . . .
H25C H 0.7123 0.4042 0.5051 0.046 Uiso 1 1 calc R U . . .
C27 C 0.4913(2) 0.2778(2) 0.2812(4) 0.0227(9) Uani 1 1 d . . . . .
H27 H 0.5291 0.2436 0.2415 0.027 Uiso 1 1 calc R U . . .
C28 C 0.4168(2) 0.2362(2) 0.3121(5) 0.0294(10) Uani 1 1 d . . . . .
H28A H 0.3768 0.2688 0.3444 0.044 Uiso 1 1 calc R U . . .
H28B H 0.4278 0.2005 0.3802 0.044 Uiso 1 1 calc R U . . .
H28C H 0.3984 0.2127 0.2313 0.044 Uiso 1 1 calc R U . . .
C29 C 0.4762(2) 0.3347(2) 0.1782(5) 0.0288(10) Uani 1 1 d . . . . .
H29A H 0.4585 0.3125 0.0956 0.043 Uiso 1 1 calc R U . . .
H29B H 0.5242 0.3612 0.1615 0.043 Uiso 1 1 calc R U . . .
H29C H 0.4360 0.3671 0.2109 0.043 Uiso 1 1 calc R U . . .
C35 C 0.6770(2) 0.1682(2) 0.5959(5) 0.0245(8) Uani 1 1 d . . . . .
H35 H 0.6870 0.1985 0.6691 0.029 Uiso 1 1 calc R U . . .
C30 C 0.6041(2) 0.17265(19) 0.5316(4) 0.0194(8) Uani 1 1 d . . . . .
C32 C 0.6524(3) 0.0809(2) 0.3813(5) 0.0323(10) Uani 1 1 d . . . . .
H32 H 0.6435 0.0514 0.3065 0.039 Uiso 1 1 calc R U . . .
C33 C 0.7222(3) 0.0772(2) 0.4475(6) 0.0389(12) Uani 1 1 d . . . . .
H33 H 0.7614 0.0451 0.4194 0.047 Uiso 1 1 calc R U . . .
C31 C 0.5948(2) 0.1274(2) 0.4230(5) 0.0245(9) Uani 1 1 d . . . . .
H31 H 0.5471 0.1285 0.3756 0.029 Uiso 1 1 calc R U . . .
C34 C 0.7346(2) 0.1208(2) 0.5558(5) 0.0340(11) Uani 1 1 d . . . . .
H34 H 0.7824 0.1186 0.6028 0.041 Uiso 1 1 calc R U . . .
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'
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
C30 Ni1 N1 178.44(17) . . ?
C30 Ni1 P1 92.72(12) . . ?
N1 Ni1 P1 86.20(10) . . ?
C30 Ni1 P2 94.85(12) . . ?
N1 Ni1 P2 86.28(10) . . ?
P1 Ni1 P2 172.13(4) . . ?
C12 P2 C24 105.74(17) . . ?
C12 P2 C27 105.85(18) . . ?
C24 P2 C27 106.67(19) . . ?
C12 P2 Ni1 101.65(14) . . ?
C24 P2 Ni1 122.10(13) . . ?
C27 P2 Ni1 113.32(13) . . ?
C2 P1 C18 105.63(18) . . ?
C2 P1 C21 106.42(17) . . ?
C18 P1 C21 105.81(18) . . ?
C2 P1 Ni1 100.69(13) . . ?
C18 P1 Ni1 113.54(13) . . ?
C21 P1 Ni1 123.15(15) . . ?
C1 N1 C13 117.7(3) . . ?
C1 N1 Ni1 120.8(2) . . ?
C13 N1 Ni1 121.4(3) . . ?
N1 C1 C2 118.0(3) . . ?
N1 C1 C6 123.5(3) . . ?
C2 C1 C6 118.4(3) . . ?
C4 C3 C2 120.4(3) . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 120.6(3) . . ?
C1 C6 C7 121.2(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 P1 125.8(3) . . ?
C1 C2 P1 112.9(3) . . ?
C6 C5 C4 123.8(3) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C14 121.2(4) . . ?
C5 C4 C14 121.2(4) . . ?
C8 C9 C10 124.2(4) . . ?
N1 C13 C8 124.2(3) . . ?
N1 C13 C12 117.6(3) . . ?
C8 C13 C12 118.1(3) . . ?
C12 C11 C10 121.1(4) . . ?
C9 C8 C13 118.5(4) . . ?
C9 C8 C7 120.4(3) . . ?
C13 C8 C7 121.1(3) . . ?
C6 C7 C8 110.8(3) . . ?
C6 C7 C16 108.7(3) . . ?
C8 C7 C16 109.2(3) . . ?
C6 C7 C17 109.1(3) . . ?
C8 C7 C17 109.7(3) . . ?
C16 C7 C17 109.2(3) . . ?
C9 C10 C11 117.0(3) . . ?
C9 C10 C15 122.0(4) . . ?
C11 C10 C15 120.9(4) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 P2 126.5(3) . . ?
C13 C12 P2 112.4(3) . . ?
C20 C18 C19 111.0(3) . . ?
C20 C18 P1 109.7(3) . . ?
C19 C18 P1 113.0(3) . . ?
C22 C21 C23 112.0(3) . . ?
C22 C21 P1 113.2(3) . . ?
C23 C21 P1 108.1(3) . . ?
C26 C24 C25 111.9(3) . . ?
C26 C24 P2 113.4(3) . . ?
C25 C24 P2 108.0(3) . . ?
C29 C27 C28 110.9(3) . . ?
C29 C27 P2 115.4(3) . . ?
C28 C27 P2 108.8(3) . . ?
C34 C35 C30 122.4(4) . . ?
C31 C30 C35 115.1(4) . . ?
C31 C30 Ni1 124.3(3) . . ?
C35 C30 Ni1 120.6(3) . . ?
C33 C32 C31 120.5(4) . . ?
C32 C33 C34 119.1(4) . . ?
C32 C31 C30 122.8(4) . . ?
C33 C34 C35 120.1(4) . . ?
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 C30 1.902(4) . ?
Ni1 N1 1.934(3) . ?
Ni1 P1 2.1623(12) . ?
Ni1 P2 2.1631(11) . ?
P2 C12 1.807(4) . ?
P2 C24 1.844(4) . ?
P2 C27 1.850(5) . ?
P1 C2 1.811(4) . ?
P1 C18 1.847(4) . ?
P1 C21 1.850(4) . ?
N1 C1 1.387(5) . ?
N1 C13 1.388(5) . ?
C1 C2 1.407(5) . ?
C1 C6 1.420(5) . ?
C3 C4 1.391(5) . ?
C3 C2 1.402(5) . ?
C6 C5 1.393(5) . ?
C6 C7 1.525(5) . ?
C5 C4 1.393(5) . ?
C4 C14 1.518(5) . ?
C9 C8 1.388(5) . ?
C9 C10 1.395(6) . ?
C13 C8 1.411(5) . ?
C13 C12 1.436(5) . ?
C11 C12 1.381(5) . ?
C11 C10 1.401(5) . ?
C8 C7 1.529(5) . ?
C7 C16 1.536(6) . ?
C7 C17 1.558(5) . ?
C10 C15 1.506(5) . ?
C18 C20 1.526(5) . ?
C18 C19 1.533(6) . ?
C21 C22 1.528(5) . ?
C21 C23 1.528(6) . ?
C24 C26 1.527(6) . ?
C24 C25 1.533(6) . ?
C27 C29 1.517(6) . ?
C27 C28 1.535(5) . ?
C35 C34 1.394(5) . ?
C35 C30 1.413(5) . ?
C30 C31 1.398(6) . ?
C32 C33 1.376(7) . ?
C32 C31 1.388(5) . ?
C33 C34 1.384(7) . ?
