#------------------------------------------------------------------------------
#$Date: 2021-12-03 22:51:28 +0200 (Fri, 03 Dec 2021) $
#$Revision: 271042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519176.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_4519176
loop_
_publ_author_name
'Bories, Cassandre C.'
'Barbazanges, Marion'
'Derat, Etienne'
'Petit, Marc'
_publ_section_title
;
 Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for
 the Hydrosilylation of Imines
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              14262
_journal_page_last               14273
_journal_paper_doi               10.1021/acscatal.1c03886
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C14 H16 N2 O'
_chemical_formula_sum            'C14 H16 N2 O'
_chemical_formula_weight         228.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.035(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7613(5)
_cell_length_b                   8.8089(4)
_cell_length_c                   15.2633(8)
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      66.44
_cell_measurement_theta_min      4.82
_cell_volume                     1254.85(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9710
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.517
_diffrn_reflns_theta_max         66.517
_diffrn_reflns_theta_min         4.819
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0368
_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)+(0.0474P)²+0.3599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1899
_reflns_number_total             2220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03886_si_003.cif
_cod_data_source_block           cas415
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519176
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81141(10) -0.06469(11) 0.63140(7) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.59501(12) 0.90146(12) 0.27041(7) 0.0339(3) Uani 1 1 d . . . . .
N2 N 0.74500(12) 0.51075(13) 0.47133(7) 0.0354(3) Uani 1 1 d . . . . .
C1 C 0.52925(17) 0.99957(18) 0.19247(10) 0.0432(4) Uani 1 1 d . . . . .
H1A H 0.556365 1.105249 0.208855 0.065 Uiso 0.5 1 calc R U P . .
H1B H 0.562424 0.969753 0.140245 0.065 Uiso 0.5 1 calc R U P . .
H1C H 0.424787 0.989642 0.175927 0.065 Uiso 0.5 1 calc R U P . .
H1D H 0.472686 0.937847 0.141163 0.065 Uiso 0.5 1 calc R U P . .
H1E H 0.466627 1.073343 0.209773 0.065 Uiso 0.5 1 calc R U P . .
H1F H 0.604263 1.053454 0.174090 0.065 Uiso 0.5 1 calc R U P . .
C2 C 0.68052(15) 0.94851(15) 0.35411(9) 0.0352(3) Uani 1 1 d . . . . .
H2 H 0.707463 1.050462 0.370990 0.042 Uiso 1 1 calc R U . . .
C3 C 0.72040(14) 0.82485(14) 0.40899(9) 0.0327(3) Uani 1 1 d . . . . .
H3 H 0.779900 0.824926 0.470638 0.039 Uiso 1 1 calc R U . . .
C4 C 0.58027(14) 0.74798(15) 0.27185(9) 0.0332(3) Uani 1 1 d . . . . .
H4 H 0.526321 0.687133 0.222337 0.040 Uiso 1 1 calc R U . . .
C5 C 0.65691(13) 0.69563(14) 0.35737(9) 0.0298(3) Uani 1 1 d . . . . .
C6 C 0.66673(14) 0.53841(14) 0.38949(9) 0.0308(3) Uani 1 1 d . . . . .
C7 C 0.58633(18) 0.42066(16) 0.32297(10) 0.0475(4) Uani 1 1 d . . . . .
H7A H 0.602519 0.320416 0.352030 0.071 Uiso 1 1 calc R U . . .
H7B H 0.620309 0.420625 0.268587 0.071 Uiso 1 1 calc R U . . .
H7C H 0.483704 0.444112 0.304899 0.071 Uiso 1 1 calc R U . . .
C8 C 0.75488(14) 0.36149(15) 0.50785(9) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.64616(16) 0.29994(16) 0.53787(10) 0.0411(4) Uani 1 1 d . . . . .
H9 H 0.560053 0.355767 0.529698 0.049 Uiso 1 1 calc R U . . .
C10 C 0.88119(14) 0.27873(15) 0.52176(9) 0.0323(3) Uani 1 1 d . . . . .
H10 H 0.957894 0.319730 0.502744 0.039 Uiso 1 1 calc R U . . .
C11 C 0.66007(15) 0.15809(16) 0.57979(10) 0.0402(4) Uani 1 1 d . . . . .
H11 H 0.584271 0.117569 0.599916 0.048 Uiso 1 1 calc R U . . .
C12 C 0.89579(14) 0.13762(15) 0.56294(9) 0.0316(3) Uani 1 1 d . . . . .
H12 H 0.982054 0.081899 0.571532 0.038 Uiso 1 1 calc R U . . .
C13 C 0.78539(14) 0.07684(15) 0.59179(8) 0.0312(3) Uani 1 1 d . . . . .
C14 C 0.6979(2) -0.1382(2) 0.65422(16) 0.0718(6) Uani 1 1 d . . . . .
H14A H 0.730610 -0.237239 0.681682 0.108 Uiso 1 1 calc R U . . .
H14B H 0.666954 -0.075861 0.698109 0.108 Uiso 1 1 calc R U . . .
H14C H 0.617505 -0.152473 0.598711 0.108 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 O1 C14 117.81(12) . . ?
C4 N1 C2 108.91(11) . . ?
C4 N1 C1 125.36(12) . . ?
C2 N1 C1 125.73(12) . . ?
C6 N2 C8 120.71(11) . . ?
C3 C2 N1 108.58(12) . . ?
C2 C3 C5 107.51(12) . . ?
N1 C4 C5 108.47(11) . . ?
C4 C5 C3 106.54(11) . . ?
C4 C5 C6 126.69(12) . . ?
C3 C5 C6 126.74(12) . . ?
N2 C6 C5 117.91(12) . . ?
N2 C6 C7 124.86(12) . . ?
C5 C6 C7 117.22(11) . . ?
C9 C8 C10 118.33(13) . . ?
C9 C8 N2 121.48(12) . . ?
C10 C8 N2 119.95(12) . . ?
C8 C9 C11 121.52(13) . . ?
C12 C10 C8 120.57(13) . . ?
C13 C11 C9 119.28(13) . . ?
C10 C12 C13 120.41(12) . . ?
O1 C13 C11 124.71(12) . . ?
O1 C13 C12 115.40(11) . . ?
C11 C13 C12 119.88(12) . . ?
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
O1 C13 1.3763(15) . ?
O1 C14 1.4119(19) . ?
N1 C4 1.3605(17) . ?
N1 C2 1.3696(17) . ?
N1 C1 1.4583(17) . ?
N2 C6 1.2823(17) . ?
N2 C8 1.4204(17) . ?
C2 C3 1.3597(19) . ?
C3 C5 1.4193(18) . ?
C4 C5 1.3799(18) . ?
C5 C6 1.4630(17) . ?
C6 C7 1.5018(19) . ?
C8 C9 1.384(2) . ?
C8 C10 1.3941(19) . ?
C9 C11 1.392(2) . ?
C10 C12 1.3813(18) . ?
C11 C13 1.3824(19) . ?
C12 C13 1.3856(19) . ?
