#------------------------------------------------------------------------------
#$Date: 2020-10-02 02:25:12 +0300 (Fri, 02 Oct 2020) $
#$Revision: 256896 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038849.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_4038849
loop_
_publ_author_name
'Zhao, Yulei'
'Guo, Xuqiang'
'Si, Zhiyao'
'Hu, Yanan'
'Sun, Ying'
'Liu, Yunlin'
'Ji, Zhongyin'
'You, Jinmao'
_publ_section_title
;
 Hydrosilane-Assisted Synthesis of Urea Derivatives from CO₂
 and Amines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02032
_journal_year                    2020
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1100(8)
_cell_length_b                   10.5470(9)
_cell_length_c                   11.7739(11)
_cell_measurement_reflns_used    1202
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.589
_cell_measurement_theta_min      2.593
_cell_volume                     1131.27(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_min         2.593
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0506
_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)+(0.0586P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1406
_reflns_number_total             2706
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c02032_si_002.cif
_cod_data_source_block           180907f
_cod_database_code               4038849
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2(4)
 -1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Riding coordinates:
 N002(H002), N003(H003)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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
O001 O -0.3767(2) -0.2236(3) 0.5021(3) 0.0568(8) Uani 1 1 d . . . . .
N002 N -0.5900(3) -0.2830(3) 0.5871(2) 0.0474(9) Uani 1 1 d . . . . .
H002 H -0.683293 -0.288779 0.577478 0.057 Uiso 1 1 d R U . . .
N003 N -0.5922(3) -0.2012(3) 0.4081(3) 0.0465(8) Uani 1 1 d . . . . .
H003 H -0.685920 -0.208768 0.413356 0.056 Uiso 1 1 d R U . . .
C004 C -0.5110(3) -0.2345(4) 0.5005(4) 0.0409(8) Uani 1 1 d . . . . .
C005 C -0.5350(4) -0.1554(3) 0.3043(3) 0.0431(9) Uani 1 1 d . . . . .
C006 C -0.5332(4) -0.3256(3) 0.6926(3) 0.0446(9) Uani 1 1 d . . . . .
C007 C -0.6037(5) -0.1922(4) 0.2049(4) 0.0624(12) Uani 1 1 d . . . . .
H007 H -0.684054 -0.246492 0.207636 0.075 Uiso 1 1 calc R U . . .
C008 C -0.3665(5) -0.0329(4) 0.1941(4) 0.0631(12) Uani 1 1 d . . . . .
H008 H -0.285683 0.020919 0.190701 0.076 Uiso 1 1 calc R U . . .
C009 C -0.4174(4) -0.0740(4) 0.2982(4) 0.0526(10) Uani 1 1 d . . . . .
H009 H -0.371926 -0.046484 0.364486 0.063 Uiso 1 1 calc R U . . .
C00A C -0.4278(4) -0.2578(4) 0.7507(3) 0.0514(10) Uani 1 1 d . . . . .
H00A H -0.389692 -0.183438 0.720108 0.062 Uiso 1 1 calc R U . . .
C00B C -0.5912(5) -0.4333(4) 0.7391(4) 0.0637(12) Uani 1 1 d . . . . .
H00B H -0.662591 -0.478905 0.700094 0.076 Uiso 1 1 calc R U . . .
C00C C -0.4337(6) -0.0706(5) 0.0959(4) 0.0698(14) Uani 1 1 d . . . . .
H00C H -0.398413 -0.043456 0.025880 0.084 Uiso 1 1 calc R U . . .
C00D C -0.3791(5) -0.3015(5) 0.8551(4) 0.0703(14) Uani 1 1 d . . . . .
H00D H -0.305937 -0.257588 0.893695 0.084 Uiso 1 1 calc R U . . .
C00E C -0.5530(6) -0.1482(5) 0.1016(4) 0.0737(14) Uani 1 1 d . . . . .
H00E H -0.600867 -0.171912 0.035163 0.088 Uiso 1 1 calc R U . . .
C00F C -0.4382(6) -0.4090(6) 0.9020(5) 0.0834(17) Uani 1 1 d . . . . .
H00F H -0.406641 -0.437321 0.972690 0.100 Uiso 1 1 calc R U . . .
C00G C -0.5437(6) -0.4741(5) 0.8440(5) 0.0834(16) Uani 1 1 d . . . . .
H00G H -0.584033 -0.547016 0.875744 0.100 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 N002 H002 117.0 . . ?
C004 N002 C006 126.0(3) . . ?
C006 N002 H002 117.0 . . ?
C004 N003 H003 117.3 . . ?
C004 N003 C005 125.4(3) . . ?
C005 N003 H003 117.3 . . ?
O001 C004 N002 123.7(4) . . ?
O001 C004 N003 121.9(4) . . ?
N002 C004 N003 114.3(3) . . ?
C007 C005 N003 117.9(3) . . ?
C009 C005 N003 123.1(3) . . ?
C009 C005 C007 119.0(4) . . ?
C00A C006 N002 121.6(4) . . ?
C00B C006 N002 118.2(4) . . ?
C00B C006 C00A 120.1(4) . . ?
C005 C007 H007 120.0 . . ?
C00E C007 C005 120.0(4) . . ?
C00E C007 H007 120.0 . . ?
C009 C008 H008 119.7 . . ?
C00C C008 H008 119.7 . . ?
C00C C008 C009 120.6(4) . . ?
C005 C009 C008 120.3(4) . . ?
C005 C009 H009 119.9 . . ?
C008 C009 H009 119.9 . . ?
C006 C00A H00A 120.3 . . ?
C006 C00A C00D 119.4(4) . . ?
C00D C00A H00A 120.3 . . ?
C006 C00B H00B 120.1 . . ?
C006 C00B C00G 119.8(5) . . ?
C00G C00B H00B 120.1 . . ?
C008 C00C H00C 120.3 . . ?
C00E C00C C008 119.4(4) . . ?
C00E C00C H00C 120.3 . . ?
C00A C00D H00D 119.8 . . ?
C00F C00D C00A 120.4(5) . . ?
C00F C00D H00D 119.8 . . ?
C007 C00E H00E 119.6 . . ?
C00C C00E C007 120.8(4) . . ?
C00C C00E H00E 119.6 . . ?
C00D C00F H00F 120.3 . . ?
C00G C00F C00D 119.5(5) . . ?
C00G C00F H00F 120.3 . . ?
C00B C00G H00G 119.6 . . ?
C00F C00G C00B 120.8(5) . . ?
C00F C00G H00G 119.6 . . ?
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
O001 C004 1.229(4) . ?
N002 H002 0.8600 . ?
N002 C004 1.349(5) . ?
N002 C006 1.418(5) . ?
N003 H003 0.8600 . ?
N003 C004 1.361(5) . ?
N003 C005 1.415(5) . ?
C005 C007 1.383(6) . ?
C005 C009 1.375(5) . ?
C006 C00A 1.379(6) . ?
C006 C00B 1.368(6) . ?
C007 H007 0.9300 . ?
C007 C00E 1.381(6) . ?
C008 H008 0.9300 . ?
C008 C009 1.380(6) . ?
C008 C00C 1.368(6) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00D 1.386(6) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.378(6) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.362(7) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.371(8) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00G 1.364(8) . ?
C00G H00G 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 C006 C00A C00D 178.0(4) . . . . ?
N002 C006 C00B C00G -176.9(4) . . . . ?
N003 C005 C007 C00E 179.1(4) . . . . ?
N003 C005 C009 C008 179.8(4) . . . . ?
C004 N002 C006 C00A 43.4(5) . . . . ?
C004 N002 C006 C00B -140.0(4) . . . . ?
C004 N003 C005 C007 143.4(4) . . . . ?
C004 N003 C005 C009 -38.2(6) . . . . ?
C005 N003 C004 O001 2.1(6) . . . . ?
C005 N003 C004 N002 -176.1(3) . . . . ?
C005 C007 C00E C00C 1.3(7) . . . . ?
C006 N002 C004 O001 1.5(6) . . . . ?
C006 N002 C004 N003 179.7(3) . . . . ?
C006 C00A C00D C00F -1.9(6) . . . . ?
C006 C00B C00G C00F -0.6(7) . . . . ?
C007 C005 C009 C008 -1.9(6) . . . . ?
C008 C00C C00E C007 -2.0(8) . . . . ?
C009 C005 C007 C00E 0.7(6) . . . . ?
C009 C008 C00C C00E 0.7(7) . . . . ?
C00A C006 C00B C00G -0.2(6) . . . . ?
C00A C00D C00F C00G 1.1(8) . . . . ?
C00B C006 C00A C00D 1.5(6) . . . . ?
C00C C008 C009 C005 1.2(6) . . . . ?
C00D C00F C00G C00B 0.1(9) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2(4)
2 -1(4)
