#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:43:34 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/01/7240118.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_7240118
loop_
_publ_author_name
'Recio, Javier'
'Filace, Fabiana'
'Gala, Elena'
'Pérez-Redondo, Adrián'
'Álvarez-Builla, Julio'
'Burgos, Carolina'
_publ_section_title
;
 Studies on the preparation of aminobipyridines and bipyridine sultams via
 an intramolecular free radical pathway
;
_journal_issue                   18
_journal_name_full               'RSC Advances'
_journal_page_first              10447
_journal_page_last               10451
_journal_paper_doi               10.1039/D0RA02026E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C11 H9 N3 O2 S'
_chemical_formula_sum            'C11 H9 N3 O2 S'
_chemical_formula_weight         247.27
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_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             2019-07-19T15:52:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                99.965(3)
_cell_angle_beta                 95.925(4)
_cell_angle_gamma                97.050(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9735(3)
_cell_length_b                   7.8762(2)
_cell_length_c                   9.8077(4)
_cell_measurement_reflns_used    70
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     522.26(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.002796
_diffrn_orient_matrix_UB_12      0.06034
_diffrn_orient_matrix_UB_13      0.09811
_diffrn_orient_matrix_UB_21      0.13111
_diffrn_orient_matrix_UB_22      -0.031656
_diffrn_orient_matrix_UB_23      0.027692
_diffrn_orient_matrix_UB_31      0.063438
_diffrn_orient_matrix_UB_32      0.111013
_diffrn_orient_matrix_UB_33      -0.022389
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.653
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.042
_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)+(0.0588P)²+0.2354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0
_reflns_number_gt                2086
_reflns_number_total             2389
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra02026e2.cif
_cod_data_source_block           5ba
_cod_depositor_comments          'Adding full bibliography for 7240118.cif.'
_cod_database_code               7240118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.6334(2) 0.3160(2) 0.36945(17) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.6144(3) 0.2364(2) 0.58047(19) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.573 0.1515 0.6333 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7134(3) 0.3946(3) 0.65157(18) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.7376 0.4182 0.7506 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7767(2) 0.5181(2) 0.57506(17) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.8455 0.628 0.6214 0.03 Uiso 1 1 calc R U . . .
C5 C 0.7389(2) 0.4805(2) 0.42996(17) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.7985(2) 0.6074(2) 0.34381(17) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.9112(3) 0.8882(2) 0.3273(2) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.9565 1.0054 0.3718 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9019(3) 0.8475(2) 0.1829(2) 0.0327(4) Uani 1 1 d . . . . .
H8 H 0.9377 0.935 0.131 0.039 Uiso 1 1 calc R U . . .
C9 C 0.8396(3) 0.6776(2) 0.11662(19) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.8314 0.6444 0.0181 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7892(2) 0.5570(2) 0.19911(17) 0.0215(3) Uani 1 1 d . . . . .
C11 C 0.4338(3) 0.1161(2) 0.1661(2) 0.0356(4) Uani 1 1 d . . . . .
H11A H 0.4964 0.0125 0.1726 0.053 Uiso 1 1 calc R U . . .
H11B H 0.3888 0.1161 0.0681 0.053 Uiso 1 1 calc R U . . .
H11C H 0.3224 0.115 0.2193 0.053 Uiso 1 1 calc R U . . .
N1 N 0.5750(2) 0.27365(18) 0.22358(15) 0.0249(3) Uani 1 1 d . . . . .
N2 N 0.5733(2) 0.19579(19) 0.44114(16) 0.0274(3) Uani 1 1 d . . . . .
N3 N 0.8609(2) 0.77380(18) 0.40751(15) 0.0260(3) Uani 1 1 d . . . . .
O1 O 0.6384(2) 0.31297(18) -0.01557(13) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.9088(2) 0.25802(16) 0.14374(14) 0.0324(3) Uani 1 1 d . . . . .
S1 S 0.73467(6) 0.33645(5) 0.12379(4) 0.02431(15) Uani 1 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.225
1 -2 0 0.336
-1 -7 0 0.416
-4 3 0 0.271
1 11 0 0.32
-1 -18 13 0.292
1 -2 -14 0.208
-1 2 14 0.203
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
N2 C1 C5 124.34(15) . . ?
N2 C1 N1 115.53(14) . . ?
C5 C1 N1 120.04(14) . . ?
N2 C2 C3 123.75(16) . . ?
N2 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C2 C3 C4 118.41(16) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 119.69(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C1 116.69(15) . . ?
C4 C5 C6 122.08(15) . . ?
C1 C5 C6 121.18(15) . . ?
N3 C6 C10 120.99(15) . . ?
N3 C6 C5 118.33(15) . . ?
C10 C6 C5 120.68(14) . . ?
N3 C7 C8 124.38(16) . . ?
N3 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
C9 C8 C7 118.65(16) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 117.51(16) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C6 120.92(15) . . ?
C9 C10 S1 119.57(13) . . ?
C6 C10 S1 119.26(12) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C11 118.98(14) . . ?
C1 N1 S1 116.57(11) . . ?
C11 N1 S1 117.70(12) . . ?
C1 N2 C2 117.10(15) . . ?
C7 N3 C6 117.53(15) . . ?
O1 S1 O2 117.39(9) . . ?
O1 S1 N1 108.33(8) . . ?
O2 S1 N1 110.93(8) . . ?
O1 S1 C10 111.02(8) . . ?
O2 S1 C10 108.02(8) . . ?
N1 S1 C10 99.71(7) . . ?
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
C1 N2 1.327(2) . ?
C1 C5 1.407(2) . ?
C1 N1 1.416(2) . ?
C2 N2 1.341(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.95 . ?
C3 C4 1.386(2) . ?
C3 H3 0.95 . ?
C4 C5 1.393(2) . ?
C4 H4 0.95 . ?
C5 C6 1.466(2) . ?
C6 N3 1.348(2) . ?
C6 C10 1.398(2) . ?
C7 N3 1.334(2) . ?
C7 C8 1.389(3) . ?
C7 H7 0.95 . ?
C8 C9 1.379(3) . ?
C8 H8 0.95 . ?
C9 C10 1.387(2) . ?
C9 H9 0.95 . ?
C10 S1 1.7445(16) . ?
C11 N1 1.473(2) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
N1 S1 1.6433(15) . ?
O1 S1 1.4303(14) . ?
O2 S1 1.4391(14) . ?
