#------------------------------------------------------------------------------
#$Date: 2020-12-04 00:26:05 +0200 (Fri, 04 Dec 2020) $
#$Revision: 259491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518277.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_4518277
loop_
_publ_author_name
'Leong, Bi-Xiang'
'Teo, Yeow-Chuan'
'Condamines, Cloé'
'Yang, Ming-Chung'
'Su, Ming-Der'
'So, Cheuk-Wai'
_publ_section_title
;
 A NHC-Silyliumylidene Cation for Catalytic N-Formylation of Amines Using
 Carbon Dioxide
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14824
_journal_page_last               14833
_journal_paper_doi               10.1021/acscatal.0c03795
_journal_year                    2020
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 111.9279(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8957(7)
_cell_length_b                   12.8359(6)
_cell_length_c                   8.4150(3)
_cell_measurement_reflns_used    3447
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.9496
_cell_measurement_theta_min      2.9483
_cell_volume                     1492.55(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9262
_diffrn_reflns_theta_full        30.99
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0482
_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)+(0.0531P)²+1.1245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1861
_reflns_number_total             2359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c03795_si_002.cif
_cod_data_source_block           scw2232m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' 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 
;
_cod_database_code               4518277
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.61191(9) 0.53505(10) 0.11986(15) 0.0213(3) Uani d . . . 1 . .
H H1 0.601481 0.464262 0.141089 0.026 Uiso calc U . R 1 . .
C C2 0.63881(8) 0.71098(9) 0.24772(14) 0.0177(2) Uani d . . . 1 . .
C C3 0.66815(9) 0.76189(10) 0.13009(15) 0.0218(3) Uani d . . . 1 . .
H H3 0.67881 0.723314 0.0424 0.026 Uiso calc U . R 1 . .
C C4 0.68209(10) 0.86943(11) 0.13989(16) 0.0257(3) Uani d . . . 1 . .
H H4 0.703235 0.903908 0.060205 0.031 Uiso calc U . R 1 . .
C C5 0.66510(10) 0.92576(10) 0.26564(17) 0.0255(3) Uani d . . . 1 . .
H H5 0.673648 0.999199 0.270846 0.031 Uiso calc U . R 1 . .
C C6 0.63560(9) 0.87606(10) 0.38467(16) 0.0226(3) Uani d . . . 1 . .
H H6 0.62382 0.915378 0.470552 0.027 Uiso calc U . R 1 . .
C C7 0.62345(8) 0.76883(10) 0.37752(14) 0.0178(2) Uani d . . . 1 . .
C C8 0.58057(10) 0.76644(11) 0.62349(17) 0.0261(3) Uani d . . . 1 . .
H H8A 0.640072 0.802549 0.694175 0.039 Uiso calc U . R 1 . .
H H8B 0.561956 0.717058 0.69457 0.039 Uiso calc U . R 1 . .
H H8C 0.528635 0.817471 0.573988 0.039 Uiso calc U . R 1 . .
N N1 0.62470(8) 0.60241(8) 0.24835(12) 0.0188(2) Uani d . . . 1 . .
H H1A 0.624229 0.575682 0.344332 0.023 Uiso calc U . R 1 . .
O O1 0.61232(8) 0.55553(8) -0.02226(11) 0.0273(2) Uani d . . . 1 . .
O O2 0.59668(7) 0.71145(7) 0.48908(11) 0.0220(2) Uani d . . . 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 126.64(12) ?
O1 C1 H1 . . 116.7 ?
N1 C1 H1 . . 116.7 ?
C3 C2 C7 . . 119.42(11) ?
C3 C2 N1 . . 123.78(11) ?
C7 C2 N1 . . 116.79(10) ?
C2 C3 C4 . . 120.29(11) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C5 C4 C3 . . 119.87(12) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.64(12) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C7 C6 C5 . . 119.71(11) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
O2 C7 C6 . . 124.95(11) ?
O2 C7 C2 . . 115.01(11) ?
C6 C7 C2 . . 120.04(11) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C1 N1 C2 . . 127.65(10) ?
C1 N1 H1A . . 116.2 ?
C2 N1 H1A . . 116.2 ?
C7 O2 C8 . . 117.18(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2267(14) ?
C1 N1 . 1.3413(15) ?
C1 H1 . 0.95 ?
C2 C3 . 1.3860(16) ?
C2 C7 . 1.4083(15) ?
C2 N1 . 1.4097(16) ?
C3 C4 . 1.3937(18) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3808(18) ?
C4 H4 . 0.95 ?
C5 C6 . 1.3901(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.3866(18) ?
C6 H6 . 0.95 ?
C7 O2 . 1.3647(13) ?
C8 O2 . 1.4275(14) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
N1 H1A . 0.88 ?
