#------------------------------------------------------------------------------
#$Date: 2020-12-04 00:26:05 +0200 (Fri, 04 Dec 2020) $
#$Revision: 259491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518276.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_4518276
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 H8 Cl N O'
_chemical_formula_weight         169.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 96.260(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1585(4)
_cell_length_b                   4.6786(2)
_cell_length_c                   26.8306(16)
_cell_measurement_reflns_used    3685
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.9458
_cell_measurement_theta_min      3.0551
_cell_volume                     768.46(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0488
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            11102
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_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    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0393
_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)+(0.0271P)²+0.5060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                1931
_reflns_number_total             2438
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c03795_si_002.cif
_cod_data_source_block           scw2221m
_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               4518276
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.7306(3) 0.5461(3) 0.39608(5) 0.0183(3) Uani d . . . 1 . .
H H1 0.792006 0.628167 0.426812 0.022 Uiso calc U . R 1 . .
C C2 0.8516(2) 0.3516(3) 0.37156(5) 0.0168(3) Uani d . . . 1 . .
H H2 0.99476 0.299326 0.38531 0.02 Uiso calc U . R 1 . .
C C3 0.7597(2) 0.2345(3) 0.32655(5) 0.0150(3) Uani d . . . 1 . .
C C4 0.5504(2) 0.3037(3) 0.30624(5) 0.0164(3) Uani d . . . 1 . .
H H4 0.489177 0.219737 0.275646 0.02 Uiso calc U . R 1 . .
C C5 0.4310(2) 0.4981(3) 0.33137(5) 0.0167(3) Uani d . . . 1 . .
H H5 0.286802 0.546627 0.317813 0.02 Uiso calc U . R 1 . .
C C6 0.5198(2) 0.6229(3) 0.37619(5) 0.0163(3) Uani d . . . 1 . .
C C7 0.3913(3) 0.8383(3) 0.40235(6) 0.0209(3) Uani d . . . 1 . .
H H7A 0.485411 1.004753 0.412257 0.025 Uiso calc U . R 1 . .
H H7B 0.2667 0.90629 0.37891 0.025 Uiso calc U . R 1 . .
C C8 0.2377(2) 0.8851(3) 0.48130(5) 0.0164(3) Uani d . . . 1 . .
H H8 0.188283 0.79562 0.509779 0.02 Uiso calc U . R 1 . .
Cl Cl1 0.91182(6) -0.00347(8) 0.29426(2) 0.01924(10) Uani d . . . 1 . .
N N1 0.30909(19) 0.7174(3) 0.44684(4) 0.0155(2) Uani d . . . 1 . .
H H1A 0.306991 0.530753 0.450787 0.019 Uiso calc U . R 1 . .
O O1 0.23031(18) 1.1484(2) 0.47937(4) 0.0205(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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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
C2 C1 C6 . . 120.87(13) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 118.83(13) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 121.62(13) ?
C4 C3 Cl1 . . 118.80(11) ?
C2 C3 Cl1 . . 119.58(11) ?
C3 C4 C5 . . 118.81(13) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C4 C5 C6 . . 120.97(13) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C1 . . 118.88(13) ?
C5 C6 C7 . . 120.47(13) ?
C1 C6 C7 . . 120.65(13) ?
N1 C7 C6 . . 111.68(12) ?
N1 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
O1 C8 N1 . . 125.17(13) ?
O1 C8 H8 . . 117.4 ?
N1 C8 H8 . . 117.4 ?
C8 N1 C7 . . 120.84(12) ?
C8 N1 H1A . . 119.6 ?
C7 N1 H1A . . 119.6 ?
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 C2 . 1.387(2) ?
C1 C6 . 1.396(2) ?
C1 H1 . 0.95 ?
C2 C3 . 1.389(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.382(2) ?
C3 Cl1 . 1.7449(14) ?
C4 C5 . 1.389(2) ?
C4 H4 . 0.95 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.502(2) ?
C7 N1 . 1.4601(19) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 O1 . 1.2335(18) ?
C8 N1 . 1.3239(18) ?
C8 H8 . 0.95 ?
N1 H1A . 0.88 ?
