#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:38:08 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/84/7128482.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_7128482
loop_
_publ_author_name
'Toda, Yasunori'
'Shishido, Minoru'
'Aoki, Tatsuya'
'Sukegawa, Kimiya'
'Suga, Hiroyuki'
_publ_section_title
;
 Switchable synthesis of cyclic carbamates by carbon dioxide fixation at
 atmospheric pressure.
;
_journal_issue                   54
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6672
_journal_page_last               6675
_journal_paper_doi               10.1039/d1cc02493k
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H12 Cl N O3'
_chemical_formula_weight         241.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0808(12)
_cell_length_b                   10.5099(14)
_cell_length_c                   11.7960(16)
_cell_measurement_reflns_used    69
_cell_measurement_temperature    93.(2)
_cell_measurement_theta_max      17.1842
_cell_measurement_theta_min      3.4208
_cell_volume                     1125.8(3)
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0939
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13280
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.60
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.181
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                1219
_reflns_number_total             2688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc02493k2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7128482.cif.'
_cod_database_code               7128482
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.94299(13) 0.28050(9) 0.34222(9) 0.0827(4) Uani d . 1 . .
O O1 0.6998(3) 0.8987(2) 0.2350(2) 0.0752(9) Uani d . 1 . .
H H1 0.7378 0.9501 0.1891 0.113 Uiso calc R 1 . .
O O2 0.6701(3) 1.0329(2) 0.4519(2) 0.0622(8) Uani d . 1 . .
O O3 0.7245(3) 0.9019(2) 0.5904(2) 0.0635(8) Uani d . 1 . .
N N1 0.5749(3) 0.8292(2) 0.4524(2) 0.0438(7) Uani d . 1 . .
C C1 0.8307(4) 0.4041(4) 0.3887(3) 0.0530(10) Uani d . 1 . .
C C2 0.7253(4) 0.3816(3) 0.4697(3) 0.0606(11) Uani d . 1 . .
H H2 0.7126 0.2987 0.5002 0.073 Uiso calc R 1 . .
C C3 0.6383(4) 0.4807(3) 0.5060(3) 0.0569(11) Uani d . 1 . .
H H3 0.565 0.4654 0.5618 0.068 Uiso calc R 1 . .
C C4 0.6554(4) 0.6030(3) 0.4626(3) 0.0457(9) Uani d . 1 . .
C C5 0.5565(4) 0.7072(3) 0.5085(3) 0.0535(9) Uani d . 1 . .
H H5A 0.4526 0.6799 0.5005 0.064 Uiso calc R 1 . .
H H5B 0.5767 0.718 0.5904 0.064 Uiso calc R 1 . .
C C6 0.4945(4) 0.8475(3) 0.3470(3) 0.0590(10) Uani d . 1 . .
H H6A 0.3914 0.8716 0.3639 0.071 Uiso calc R 1 . .
H H6B 0.4932 0.767 0.3035 0.071 Uiso calc R 1 . .
C C7 0.5666(4) 0.9503(3) 0.2775(3) 0.0580(10) Uani d . 1 . .
H H7 0.5008 0.9736 0.2127 0.07 Uiso calc R 1 . .
C C8 0.5907(4) 1.0639(3) 0.3500(3) 0.0653(11) Uani d . 1 . .
H H8A 0.6467 1.1284 0.3067 0.078 Uiso calc R 1 . .
H H8B 0.4943 1.1013 0.3705 0.078 Uiso calc R 1 . .
C C9 0.6573(4) 0.9186(3) 0.5014(3) 0.0485(9) Uani d . 1 . .
C C10 0.7614(4) 0.6221(3) 0.3812(3) 0.0472(9) Uani d . 1 . .
H H10 0.7746 0.7047 0.3502 0.057 Uiso calc R 1 . .
C C11 0.8495(4) 0.5228(3) 0.3433(3) 0.0524(9) Uani d . 1 . .
H H11 0.9219 0.5371 0.2865 0.063 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
C7 O1 H1 . . 109.5 ?
C9 O2 C8 . . 121.5(3) ?
C9 N1 C5 . . 119.3(3) ?
C9 N1 C6 . . 124.0(3) ?
C5 N1 C6 . . 116.6(3) ?
C11 C1 C2 . . 121.1(4) ?
C11 C1 Cl1 . . 119.0(3) ?
C2 C1 Cl1 . . 119.9(3) ?
C1 C2 C3 . . 119.1(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 121.4(4) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C10 C4 C3 . . 118.0(4) ?
C10 C4 C5 . . 124.0(3) ?
C3 C4 C5 . . 118.0(3) ?
N1 C5 C4 . . 114.0(3) ?
N1 C5 H5A . . 108.8 ?
C4 C5 H5A . . 108.8 ?
N1 C5 H5B . . 108.8 ?
C4 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.6 ?
N1 C6 C7 . . 110.0(3) ?
N1 C6 H6A . . 109.7 ?
C7 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C7 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
O1 C7 C8 . . 112.7(3) ?
O1 C7 C6 . . 106.8(3) ?
C8 C7 C6 . . 109.1(3) ?
O1 C7 H7 . . 109.4 ?
C8 C7 H7 . . 109.4 ?
C6 C7 H7 . . 109.4 ?
O2 C8 C7 . . 111.9(3) ?
O2 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
O2 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
O3 C9 N1 . . 123.3(3) ?
O3 C9 O2 . . 117.2(4) ?
N1 C9 O2 . . 119.5(3) ?
C4 C10 C11 . . 121.3(3) ?
C4 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C1 C11 C10 . . 119.1(3) ?
C1 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
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
Cl1 C1 . 1.740(4) ?
O1 C7 . 1.417(4) ?
O1 H1 . 0.84 ?
O2 C9 . 1.341(4) ?
O2 C8 . 1.439(4) ?
O3 C9 . 1.227(4) ?
N1 C9 . 1.332(4) ?
N1 C5 . 1.453(3) ?
N1 C6 . 1.454(4) ?
C1 C11 . 1.369(4) ?
C1 C2 . 1.373(4) ?
C2 C3 . 1.376(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.392(4) ?
C3 H3 . 0.95 ?
C4 C10 . 1.375(4) ?
C4 C5 . 1.516(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.506(4) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.484(5) ?
C7 H7 . 1.0 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C10 C11 . 1.389(4) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
