#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032726.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_4032726
loop_
_publ_author_name
'Otevrel, Jan'
'Bobal, Pavel'
_publ_section_title
;
 Diamine-Tethered Bis(thiourea) Organocatalyst for Asymmetric Henry
 Reaction.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8342
_journal_page_last               8358
_journal_paper_doi               10.1021/acs.joc.7b00079
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C8 H9 N2 O2'
_chemical_formula_weight         165.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.9866(13)
_cell_length_b                   7.9950(6)
_cell_length_c                   11.8016(9)
_cell_measurement_reflns_used    13068
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1602.8(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  Multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6318
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'Rotating Anode MicroMax-007HF DW 1.2 kW'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
XDS
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0326
_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)+(0.0500P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1299
_reflns_number_total             1396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00079_si_002.cif
_cod_data_source_block           0915
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4032726
_shelx_shelxl_version_number     2014/7
_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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
C1 C 0.43713(6) 0.14648(14) 0.12163(9) 0.0181(3) Uani 1 1 d . .
C2 C 0.50022(6) 0.20486(13) 0.18659(9) 0.0167(3) Uani 1 1 d . .
C3 C 0.56345(6) 0.27843(13) 0.12690(9) 0.0180(3) Uani 1 1 d . .
C4 C 0.56066(7) 0.28797(14) 0.00857(9) 0.0210(3) Uani 1 1 d . .
H4 H 0.6041 0.3343 -0.0313 0.025 Uiso 1 1 calc R U
C5 C 0.49593(7) 0.23127(14) -0.05165(10) 0.0218(3) Uani 1 1 d . .
H5 H 0.4950 0.2408 -0.1319 0.026 Uiso 1 1 calc R U
C6 C 0.43284(7) 0.16096(14) 0.00471(9) 0.0203(3) Uani 1 1 d . .
H6 H 0.3877 0.1235 -0.0355 0.024 Uiso 1 1 calc R U
N7 N 0.37285(5) 0.05058(12) 0.17433(8) 0.0215(3) Uani 1 1 d . .
O8 O 0.38934(5) -0.04284(10) 0.25374(7) 0.0238(2) Uani 1 1 d . .
O9 O 0.30688(5) 0.06214(13) 0.13268(7) 0.0346(3) Uani 1 1 d . .
N10 N 0.63057(5) 0.33315(12) 0.18816(8) 0.0201(3) Uani 1 1 d . .
C11 C 0.70527(7) 0.32722(19) 0.12738(11) 0.0315(3) Uani 1 1 d . .
H11A H 0.7098 0.2201 0.0875 0.047 Uiso 1 1 calc R U
H11B H 0.7488 0.3386 0.1814 0.047 Uiso 1 1 calc R U
H11C H 0.7074 0.4190 0.0724 0.047 Uiso 1 1 calc R U
C12 C 0.62152(7) 0.48992(16) 0.24974(11) 0.0277(3) Uani 1 1 d . .
H12A H 0.6226 0.5835 0.1962 0.042 Uiso 1 1 calc R U
H12B H 0.6647 0.5021 0.3041 0.042 Uiso 1 1 calc R U
H12C H 0.5712 0.4896 0.2903 0.042 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_3
C6 C1 C2 123.93(10) .
C6 C1 N7 115.14(9) .
C2 C1 N7 120.72(9) .
C1 C2 C3 116.64(10) .
C1 C2 C2 122.99(11) 4_655
C3 C2 C2 120.16(10) 4_655
C4 C3 C2 119.64(10) .
C4 C3 N10 121.25(10) .
C2 C3 N10 119.02(10) .
C5 C4 C3 121.40(10) .
C6 C5 C4 120.13(10) .
C5 C6 C1 118.19(10) .
O9 N7 O8 123.95(10) .
O9 N7 C1 117.96(9) .
O8 N7 C1 117.97(9) .
C3 N10 C12 115.75(9) .
C3 N10 C11 116.00(9) .
C12 N10 C11 111.42(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3867(15) .
C1 C2 1.3978(15) .
C1 N7 1.4720(14) .
C2 C3 1.4127(15) .
C2 C2 1.497(2) 4_655
C3 C4 1.3994(16) .
C3 N10 1.4192(14) .
C4 C5 1.3854(16) .
C5 C6 1.3810(16) .
N7 O9 1.2272(13) .
N7 O8 1.2307(13) .
N10 C12 1.4570(16) .
N10 C11 1.4583(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O8 0.95 2.57 3.1953(13) 123.7 8
C12 H12B O9 0.98 2.57 3.4889(15) 155.7 6_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095308
