#------------------------------------------------------------------------------
#$Date: 2018-11-10 03:50:31 +0100 (Sat 10 de Nov de 2018) $
#$Revision: 211883 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/17/7231784.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_7231784
loop_
_publ_author_name
'Ibrahim, Hamada Mohamed'
'Ahmed Arafa, Wael Abdelgayed'
'Behbehani, Haider'
_publ_section_title
;
 l-Proline catalyzed one-pot synthesis of polysubstituted pyridine system
 incorporating benzothiazole moiety via sustainable sonochemical approach
;
_journal_issue                   66
_journal_name_full               'RSC Advances'
_journal_page_first              37606
_journal_paper_doi               10.1039/C8RA07013J
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C20 H11 N5 O S'
_chemical_formula_weight         369.40
_chemical_name_common            Hamada_BT4_24_07_11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-07-26 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                93.9110(10)
_cell_angle_beta                 94.6660(10)
_cell_angle_gamma                94.2320(10)
_cell_formula_units_Z            2
_cell_length_a                   6.43370(10)
_cell_length_b                   11.1793(3)
_cell_length_c                   12.2318(3)
_cell_measurement_reflns_used    9007
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      66.1336
_cell_measurement_theta_min      3.6357
_cell_volume                     872.02(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14792
_diffrn_reflns_theta_full        66.44
_diffrn_reflns_theta_max         66.44
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.684
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.684
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0347
_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)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2793
_reflns_number_total             3014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ra07013j2.cif
_cod_data_source_block           I
_cod_database_code               7231784
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.19450(5) 0.42184(3) -0.06969(3) 0.05443(17) Uani d . 1
C C7 0.4116(2) 0.33738(11) -0.05424(11) 0.0438(3) Uani d . 1
C C8 0.59892(19) 0.18084(11) 0.03618(10) 0.0423(3) Uani d . 1
C C10 0.46137(19) 0.09273(11) 0.19867(10) 0.0431(3) Uani d . 1
C C11 0.3098(2) 0.17495(12) 0.19631(10) 0.0445(3) Uani d . 1
C C12 0.2866(2) 0.25599(12) 0.11137(11) 0.0456(3) Uani d . 1
C C9 0.60358(19) 0.09713(11) 0.11764(10) 0.0436(3) Uani d . 1
C C20 0.1717(2) 0.18886(12) 0.28100(12) 0.0488(3) Uani d . 1
C C19 0.7555(2) 0.01115(12) 0.10792(10) 0.0462(3) Uani d . 1
C C13 0.4713(2) 0.00248(11) 0.28165(10) 0.0455(3) Uani d . 1
C C6 0.4873(2) 0.43069(12) -0.20118(11) 0.0490(3) Uani d . 1
C C5 0.6015(3) 0.46647(13) -0.28743(13) 0.0579(4) Uani d . 1
H H5 0.7285 0.4352 -0.2993 0.069 Uiso calc R 1
C C18 0.2925(2) -0.06776(12) 0.30139(12) 0.0532(3) Uani d . 1
H H18 0.1648 -0.0569 0.2634 0.064 Uiso calc R 1
C C1 0.2976(2) 0.47824(12) -0.18382(12) 0.0518(3) Uani d . 1
C C3 0.3317(3) 0.59646(15) -0.33607(14) 0.0670(4) Uani d . 1
H H3 0.2809 0.6521 -0.3826 0.08 Uiso calc R 1
C C14 0.6605(2) -0.01387(14) 0.34048(11) 0.0554(4) Uani d . 1
H H14 0.781 0.033 0.3285 0.066 Uiso calc R 1
C C2 0.2190(3) 0.56331(15) -0.25183(14) 0.0649(4) Uani d . 1
H H2 0.0935 0.5962 -0.2398 0.078 Uiso calc R 1
C C4 0.5217(3) 0.54875(14) -0.35416(13) 0.0625(4) Uani d . 1
H H4 0.5951 0.5731 -0.4123 0.075 Uiso calc R 1
C C16 0.4935(3) -0.16939(16) 0.43456(14) 0.0729(5) Uani d . 1
H H16 0.5011 -0.2275 0.4853 0.087 Uiso calc R 1
C C17 0.3042(3) -0.15373(14) 0.37741(14) 0.0667(4) Uani d . 1
H H17 0.1847 -0.201 0.3901 0.08 Uiso calc R 1
C C15 0.6695(3) -0.09979(16) 0.41682(13) 0.0674(4) Uani d . 1
H H15 0.796 -0.1101 0.4562 0.081 Uiso calc R 1
O O1 0.14494(17) 0.32314(10) 0.10379(9) 0.0602(3) Uani d . 1
N N2 0.43788(16) 0.25856(9) 0.03183(9) 0.0430(3) Uani d . 1
N N1 0.54706(19) 0.35016(11) -0.12603(10) 0.0510(3) Uani d . 1
N N3 0.73808(18) 0.18499(11) -0.03662(10) 0.0535(3) Uani d . 1
H H3A 0.73 0.2353 -0.0867 0.064 Uiso calc R 1
H H3B 0.8372 0.1374 -0.0342 0.064 Uiso calc R 1
N N4 0.8784(2) -0.05554(12) 0.09285(10) 0.0579(3) Uani d . 1
N N5 0.0639(2) 0.20485(12) 0.34958(11) 0.0637(4) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 S1 C7 88.12(6)
N1 C7 N2 121.87(11)
N1 C7 S1 115.97(10)
N2 C7 S1 122.16(9)
N3 C8 N2 119.71(12)
N3 C8 C9 121.60(11)
N2 C8 C9 118.66(11)
C11 C10 C9 117.20(12)
C11 C10 C13 121.74(12)
C9 C10 C13 121.04(11)
C10 C11 C20 122.57(12)
C10 C11 C12 122.55(12)
C20 C11 C12 114.83(11)
O1 C12 N2 118.71(12)
O1 C12 C11 123.36(12)
N2 C12 C11 117.93(11)
C10 C9 C8 123.06(11)
C10 C9 C19 121.60(12)
C8 C9 C19 115.22(11)
N5 C20 C11 177.20(15)
N4 C19 C9 175.25(14)
C18 C13 C14 119.12(12)
C18 C13 C10 120.53(12)
C14 C13 C10 120.36(12)
N1 C6 C1 114.04(12)
N1 C6 C5 125.52(13)
C1 C6 C5 120.43(12)
C4 C5 C6 118.36(14)
C17 C18 C13 120.11(14)
C6 C1 C2 120.62(13)
C6 C1 S1 110.62(10)
C2 C1 S1 128.72(12)
C2 C3 C4 121.49(14)
C15 C14 C13 120.09(14)
C3 C2 C1 118.15(15)
C5 C4 C3 120.94(14)
C15 C16 C17 120.29(14)
C16 C17 C18 120.04(15)
C16 C15 C14 120.33(15)
C8 N2 C7 121.76(11)
C8 N2 C12 120.32(11)
C7 N2 C12 117.83(10)
C7 N1 C6 111.24(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7307(14)
S1 C7 1.7478(13)
C7 N1 1.2938(18)
C7 N2 1.4257(17)
C8 N3 1.3137(17)
C8 N2 1.4006(16)
C8 C9 1.4128(18)
C10 C11 1.3883(18)
C10 C9 1.4034(19)
C10 C13 1.4801(18)
C11 C20 1.4266(19)
C11 C12 1.4303(18)
C12 O1 1.2245(16)
C12 N2 1.4314(17)
C9 C19 1.4263(18)
C20 N5 1.1445(18)
C19 N4 1.1435(18)
C13 C18 1.392(2)
C13 C14 1.393(2)
C6 N1 1.3819(17)
C6 C1 1.393(2)
C6 C5 1.397(2)
C5 C4 1.371(2)
C18 C17 1.384(2)
C1 C2 1.401(2)
C3 C2 1.363(2)
C3 C4 1.397(2)
C14 C15 1.385(2)
C16 C15 1.367(3)
C16 C17 1.383(3)
