#------------------------------------------------------------------------------
#$Date: 2019-04-18 01:26:17 +0300 (Thu, 18 Apr 2019) $
#$Revision: 214674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/09/1550910.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_1550910
loop_
_publ_author_name
'Yang, Yi'
'Zhou, Qinghai'
'Cai, Junjie'
'Xue, Teng'
'Liu, Yingle'
'Jiang, Yan'
'Su, Yumei'
'Chung, Lung Wa'
'Vicic, David A.'
_publ_section_title
;
 Exploiting the Trifluoroethyl Group as a Precatalyst Ligand in
 Nickel-catalyzed Suzuki-type Alkylations
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00554D
_journal_year                    2019
_chemical_formula_sum            'C18 H12 F6 N2 Ni O'
_chemical_formula_weight         445.01
_chemical_name_systematic        (bpy)Ni(CH2CF3)2
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-11 deposited with the CCDC.    2019-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5603(9)
_cell_length_b                   14.7597(9)
_cell_length_c                   8.5960(5)
_cell_measurement_temperature    145(2)
_cell_volume                     1847.32(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      145(2)
_diffrn_measured_fraction_theta_full 0.543
_diffrn_measured_fraction_theta_max 0.582
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.543
_diffrn_reflns_Laue_measured_fraction_max 0.582
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9460
_diffrn_reflns_point_group_measured_fraction_full 0.543
_diffrn_reflns_point_group_measured_fraction_max 0.582
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.636
_diffrn_reflns_theta_min         3.076
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       platelet
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0579
_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)+(0.0514P)²+6.1556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1465
_reflns_number_total             1669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc00554d2.cif
_cod_data_source_block           ddd_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1550910
_shelx_shelxl_version_number     2014/7
_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   0.663
_shelx_estimated_absorpt_t_max   0.978
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
Ni1 Ni 0.0000 0.34934(4) 0.7500 0.02020(19) Uani 1 2 d S T P
O1 O 0.5000 0.3193(3) 0.7500 0.0470(12) Uani 1 2 d S T P
F1 F 0.1927(2) 0.15422(19) 0.6247(4) 0.0497(8) Uani 1 1 d . . .
F2 F 0.13746(18) 0.1801(2) 0.8506(3) 0.0421(6) Uani 1 1 d . . .
F3 F 0.21540(16) 0.28262(17) 0.7344(4) 0.0410(6) Uani 1 1 d . . .
N1 N 0.06945(19) 0.4501(2) 0.6556(4) 0.0231(6) Uani 1 1 d . . .
C1 C 0.0650(2) 0.2544(2) 0.6380(4) 0.0234(6) Uani 1 1 d . . .
C2 C 0.1500(2) 0.2193(2) 0.7104(5) 0.0288(7) Uani 1 1 d . . .
C3 C 0.1434(2) 0.4455(3) 0.5618(5) 0.0293(7) Uani 1 1 d . . .
C4 C 0.1892(3) 0.5220(3) 0.5093(5) 0.0346(8) Uani 1 1 d . . .
C5 C 0.1591(3) 0.6063(3) 0.5529(5) 0.0345(8) Uani 1 1 d . . .
C6 C 0.0831(3) 0.6122(3) 0.6488(5) 0.0317(8) Uani 1 1 d . . .
C7 C 0.0404(2) 0.5337(2) 0.6983(4) 0.0228(6) Uani 1 1 d . . .
C8 C 0.4483(6) 0.4641(5) 0.761(4) 0.243(13) Uani 1 1 d . . .
C9 C 0.4215(4) 0.3764(4) 0.7667(9) 0.0574(14) Uani 1 1 d . . .
H1B H 0.077(3) 0.281(3) 0.531(5) 0.023(10) Uiso 1 1 d . . .
H5A H 0.182(4) 0.662(3) 0.511(6) 0.029(12) Uiso 1 1 d . . .
H1A H 0.029(3) 0.202(3) 0.627(6) 0.032(12) Uiso 1 1 d . . .
H6A H 0.060(4) 0.672(4) 0.664(8) 0.047(16) Uiso 1 1 d . . .
H4A H 0.242(3) 0.510(4) 0.445(6) 0.044(14) Uiso 1 1 d . . .
H3A H 0.161(4) 0.385(4) 0.538(6) 0.030(12) 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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
C1 Ni1 C1 87.9(2) . 2_556
C1 Ni1 N1 95.11(13) . .
C1 Ni1 N1 174.64(14) 2_556 .
C1 Ni1 N1 174.64(14) . 2_556
C1 Ni1 N1 95.11(13) 2_556 2_556
N1 Ni1 N1 82.21(17) . 2_556
C9 O1 C9 107.7(5) . 2_656
C3 N1 C7 117.3(3) . .
C3 N1 Ni1 128.2(2) . .
C7 N1 Ni1 114.5(2) . .
C2 C1 Ni1 116.9(3) . .
C2 C1 H1B 112(3) . .
Ni1 C1 H1B 105(2) . .
C2 C1 H1A 103(3) . .
Ni1 C1 H1A 112(3) . .
H1B C1 H1A 109(4) . .
F3 C2 F2 104.9(3) . .
F3 C2 F1 104.3(3) . .
F2 C2 F1 104.1(3) . .
F3 C2 C1 114.3(3) . .
F2 C2 C1 114.3(3) . .
F1 C2 C1 113.7(3) . .
N1 C3 C4 122.6(4) . .
N1 C3 H3A 113(3) . .
C4 C3 H3A 125(3) . .
C5 C4 C3 119.7(4) . .
C5 C4 H4A 125(4) . .
C3 C4 H4A 115(4) . .
C4 C5 C6 118.4(3) . .
C4 C5 H5A 124(3) . .
C6 C5 H5A 117(3) . .
C7 C6 C5 119.5(4) . .
C7 C6 H6A 125(4) . .
C5 C6 H6A 115(4) . .
N1 C7 C6 122.6(3) . .
N1 C7 C7 114.37(18) . 2_556
C6 C7 C7 123.0(2) . 2_556
C9 C8 C8 106.9(4) . 2_656
C8 C9 O1 109.2(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.947(3) .
Ni1 C1 1.947(3) 2_556
Ni1 N1 1.974(3) .
Ni1 N1 1.974(3) 2_556
O1 C9 1.427(6) .
O1 C9 1.427(6) 2_656
F1 C2 1.363(4) .
F2 C2 1.350(5) .
F3 C2 1.350(4) .
N1 C3 1.348(4) .
N1 C7 1.355(4) .
C1 C2 1.477(5) .
C1 H1B 1.01(5) .
C1 H1A 0.94(5) .
C3 C4 1.387(5) .
C3 H3A 0.95(5) .
C4 C5 1.372(6) .
C4 H4A 0.97(5) .
C5 C6 1.385(6) .
C5 H5A 0.95(5) .
C6 C7 1.382(5) .
C6 H6A 0.95(6) .
C7 C7 1.477(6) 2_556
C8 C9 1.354(10) .
C8 C8 1.517(17) 2_656
