#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/58/1555841.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_1555841
loop_
_publ_author_name
'Andeme Edzang, Judicaelle'
'Chen, Zhongrui'
'Audi, Hassib'
'Canard, Gabriel'
'Siri, Olivier'
_publ_section_title
;
 Transamination at the Crossroad of the One-Pot Synthesis of N-Substituted
 Quinonediimines and C-Substituted Benzobisimidazoles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5340
_journal_page_last               5343
_journal_paper_doi               10.1021/acs.orglett.6b02640
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H13 N2 O S'
_chemical_formula_sum            'C12 H13 N2 O S'
_chemical_formula_weight         233.3
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2013-10-16T15:36:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.475(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8328(1)
_cell_length_b                   14.6676(3)
_cell_length_c                   14.1401(3)
_cell_measurement_reflns_used    10188
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      29.566
_cell_measurement_theta_min      2.045
_cell_measurement_wavelength     0.71073
_cell_volume                     1160.06(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10188
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29.566
_diffrn_reflns_theta_min         2.045
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0915P)²+0.3097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2478
_reflns_number_total             3155
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02640_si_003.cif
_cod_data_source_block           ha24
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555841
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.99
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_calc_flag
C1 C -0.1938(3) -0.62123(10) 0.68326(11) 0.0240(3) Uani 1 d
C2 C -0.0680(3) -0.68115(10) 0.76444(11) 0.0250(3) Uani 1 d
C3 C 0.1383(3) -0.72624(13) 0.75875(14) 0.0346(4) Uani 1 d
H3 H 0.203(4) -0.7174(16) 0.7037(17) 0.042 Uiso 1 d
C4 C 0.2517(4) -0.78827(14) 0.83105(16) 0.0410(5) Uani 1 d
H4 H 0.393(5) -0.8195(17) 0.8243(18) 0.049 Uiso 1 d
C5 C 0.1611(4) -0.80501(13) 0.90995(15) 0.0383(4) Uani 1 d
H5 H 0.235(4) -0.8481(17) 0.9527(17) 0.046 Uiso 1 d
C6 C -0.0397(4) -0.75907(13) 0.91746(14) 0.0356(4) Uani 1 d
H6 H -0.099(4) -0.7704(16) 0.9672(17) 0.043 Uiso 1 d
C7 C -0.1553(3) -0.69714(12) 0.84515(12) 0.0301(4) Uani 1 d
H7 H -0.292(4) -0.6695(16) 0.8542(14) 0.036 Uiso 1 d
C8 C -0.3094(3) -0.55711(10) 0.54115(11) 0.0218(3) Uani 1 d
C9 C -0.4714(3) -0.52847(10) 0.59398(11) 0.0218(3) Uani 1 d
C10 C -0.6646(3) -0.47165(11) 0.55565(12) 0.0239(3) Uani 1 d
C11 C -0.4788(5) -0.84305(17) 0.5808(2) 0.0600(7) Uani 1 d
H11A H -0.533 -0.8678 0.5145 0.09 Uiso 1 calc
H11B H -0.3733 -0.7917 0.5815 0.09 Uiso 1 calc
H11C H -0.6156 -0.8229 0.6014 0.09 Uiso 1 calc
H11 H -0.774(5) -0.452(2) 0.592(2) 0.072 Uiso 1 d
C12 C -0.1084(5) -0.9513(2) 0.5971(2) 0.0650(8) Uani 1 d
H12A H -0.0075 -1.002 0.6278 0.097 Uiso 1 calc
H12B H -0.0104 -0.8977 0.5984 0.097 Uiso 1 calc
H12C H -0.1913 -0.9667 0.5293 0.097 Uiso 1 calc
N1 N -0.3910(3) -0.57135(9) 0.68455(10) 0.0243(3) Uani 1 d
H1N H -0.435(4) -0.5584(14) 0.7376(16) 0.029 Uiso 1 d
N2 N -0.1388(2) -0.61511(9) 0.59899(10) 0.0252(3) Uani 1 d
O1 O -0.4845(3) -1.01044(11) 0.64609(11) 0.0455(4) Uani 1 d
S1 S -0.32175(10) -0.92867(4) 0.66301(4) 0.0429(2) Uani 1 d
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N2 C1 N1 113.30(14) . .
N2 C1 C2 123.43(14) . .
N1 C1 C2 123.09(14) . .
C7 C2 C3 119.22(15) . .
C7 C2 C1 121.57(15) . .
C3 C2 C1 119.15(15) . .
C4 C3 C2 120.45(17) . .
C4 C3 H3 118.0(14) . .
C2 C3 H3 121.5(14) . .
C5 C4 C3 119.92(19) . .
C5 C4 H4 121.6(15) . .
C3 C4 H4 118.5(15) . .
C6 C5 C4 120.05(17) . .
C6 C5 H5 123.2(15) . .
C4 C5 H5 116.7(15) . .
C5 C6 C7 120.46(17) . .
C5 C6 H6 120.2(15) . .
C7 C6 H6 119.3(16) . .
C6 C7 C2 119.87(17) . .
C6 C7 H7 116.0(13) . .
C2 C7 H7 124.1(13) . .
N2 C8 C10 128.52(14) . 3_446
N2 C8 C9 110.09(13) . .
C10 C8 C9 121.37(14) 3_446 .
C10 C9 N1 131.39(14) . .
C10 C9 C8 124.09(14) . .
N1 C9 C8 104.50(13) . .
C9 C10 C8 114.53(14) . 3_446
C9 C10 H11 123.7(18) . .
C8 C10 H11 121.8(18) 3_446 .
S1 C11 H11A 109.5 . .
S1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
S1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
S1 C12 H12A 109.5 . .
S1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
S1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C1 N1 C9 107.23(13) . .
C1 N1 H1N 125.2(14) . .
C9 N1 H1N 126.0(14) . .
C1 N2 C8 104.87(13) . .
O1 S1 C11 105.89(11) . .
O1 S1 C12 105.68(13) . .
C11 S1 C12 95.50(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.322(2) .
C1 N1 1.368(2) .
C1 C2 1.466(2) .
C2 C7 1.395(2) .
C2 C3 1.395(2) .
C3 C4 1.388(2) .
C3 H3 0.96(2) .
C4 C5 1.385(3) .
C4 H4 0.97(3) .
C5 C6 1.381(3) .
C5 H5 0.90(2) .
C6 C7 1.391(2) .
C6 H6 0.88(2) .
C7 H7 0.93(2) .
C8 N2 1.386(2) .
C8 C10 1.399(2) 3_446
C8 C9 1.424(2) .
C9 C10 1.383(2) .
C9 N1 1.384(2) .
C10 C8 1.399(2) 3_446
C10 H11 0.97(3) .
C11 S1 1.779(3) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C11 H11C 0.97 .
C12 S1 1.785(3) .
C12 H12A 0.97 .
C12 H12B 0.97 .
C12 H12C 0.97 .
N1 H1N 0.88(2) .
O1 S1 1.5060(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305489
