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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/31/4033103.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_4033103
loop_
_publ_author_name
'Gattu, Radhakrishna'
'Bagdi, Prasanta Ray'
'Basha, R. Sidick'
'Khan, Abu T.'
_publ_section_title
;
 Camphorsulfonic Acid Catalyzed One-Pot Three-Component Reaction for the
 Synthesis of Fused Quinoline and Benzoquinoline Derivatives.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12416
_journal_page_last               12429
_journal_paper_doi               10.1021/acs.joc.7b02159
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C22 H19 N S'
_chemical_formula_weight         329.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.581(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3709(13)
_cell_length_b                   16.766(2)
_cell_length_c                   10.7394(13)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.969
_cell_measurement_theta_min      0.948
_cell_volume                     1698.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26463
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             696.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.006(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0566
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2349
_reflns_number_gt                2283
_reflns_number_total             3000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02159_si_002.cif
_cod_data_source_block           1_compound_6n
_cod_depositor_comments
'Adding full bibliography for 4033102--4033107.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4033103
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.0824(2) 0.00015(10) 0.19962(17) 0.0534(5) Uani 1 1 d .
S1 S -0.36107(7) 0.05527(4) 0.00104(7) 0.0730(3) Uani 1 1 d .
C1 C -0.4493(3) 0.07703(16) -0.1685(3) 0.0751(8) Uani 1 1 d .
H1 H -0.5473 0.0746 -0.2166 0.090 Uiso 1 1 calc R
C2 C -0.3590(3) 0.09827(15) -0.2245(3) 0.0734(8) Uani 1 1 d .
H2 H -0.3885 0.1117 -0.3162 0.088 Uiso 1 1 calc R
C3 C -0.2170(3) 0.09788(14) -0.1303(2) 0.0634(6) Uani 1 1 d .
H3 H -0.1423 0.1111 -0.1529 0.076 Uiso 1 1 calc R
C4 C -0.1991(2) 0.07573(12) -0.0001(2) 0.0549(6) Uani 1 1 d .
C5 C -0.0709(2) 0.06271(12) 0.1286(2) 0.0515(5) Uani 1 1 d .
C6 C 0.0485(3) 0.11310(13) 0.1723(2) 0.0560(6) Uani 1 1 d .
C7 C 0.0520(3) 0.18812(14) 0.0962(3) 0.0714(7) Uani 1 1 d .
H7A H 0.0790 0.2325 0.1599 0.086 Uiso 1 1 calc R
H7B H -0.0426 0.1987 0.0269 0.086 Uiso 1 1 calc R
C8 C 0.1545(4) 0.1839(2) 0.0271(3) 0.0980(11) Uani 1 1 d .
H8A H 0.1447 0.1324 -0.0170 0.118 Uiso 1 1 calc R
H8B H 0.1287 0.2246 -0.0434 0.118 Uiso 1 1 calc R
C9 C 0.3077(5) 0.1957(3) 0.1260(5) 0.1332(16) Uani 1 1 d .
H9A H 0.3649 0.1895 0.0744 0.160 Uiso 1 1 calc R
H9B H 0.3181 0.2505 0.1572 0.160 Uiso 1 1 calc R
C10 C 0.3703(4) 0.1447(3) 0.2480(5) 0.1146(13) Uani 1 1 d .
H10A H 0.4677 0.1612 0.3002 0.137 Uiso 1 1 calc R
H10B H 0.3723 0.0902 0.2183 0.137 Uiso 1 1 calc R
C11 C 0.2947(3) 0.1457(2) 0.3415(3) 0.0912(9) Uani 1 1 d .
H11A H 0.2674 0.2001 0.3495 0.109 Uiso 1 1 calc R
H11B H 0.3601 0.1282 0.4319 0.109 Uiso 1 1 calc R
C12 C 0.1640(3) 0.09348(15) 0.2936(3) 0.0649(7) Uani 1 1 d .
C13 C 0.1554(3) 0.02574(14) 0.3694(2) 0.0632(6) Uani 1 1 d .
C14 C 0.0278(3) -0.01818(12) 0.3186(2) 0.0556(6) Uani 1 1 d .
C15 C 0.0108(3) -0.08659(14) 0.3947(2) 0.0652(7) Uani 1 1 d .
C16 C -0.1145(3) -0.13243(15) 0.3454(3) 0.0730(8) Uani 1 1 d .
H16 H -0.1877 -0.1200 0.2614 0.088 Uiso 1 1 calc R
C17 C -0.1292(4) -0.19539(17) 0.4205(3) 0.0917(10) Uani 1 1 d .
H17 H -0.2125 -0.2251 0.3871 0.110 Uiso 1 1 calc R
C18 C -0.0205(6) -0.2149(2) 0.5458(4) 0.1103(14) Uani 1 1 d .
H18 H -0.0315 -0.2573 0.5964 0.132 Uiso 1 1 calc R
C19 C 0.1019(6) -0.1722(2) 0.5946(3) 0.1064(13) Uani 1 1 d .
H19 H 0.1739 -0.1859 0.6786 0.128 Uiso 1 1 calc R
C20 C 0.1226(4) -0.10695(17) 0.5200(3) 0.0783(9) Uani 1 1 d .
C21 C 0.2500(4) -0.0615(2) 0.5674(3) 0.0901(10) Uani 1 1 d .
H21 H 0.3238 -0.0750 0.6505 0.108 Uiso 1 1 calc R
C22 C 0.2669(3) -0.0001(2) 0.4964(3) 0.0835(8) Uani 1 1 d .
H22 H 0.3531 0.0268 0.5300 0.100 Uiso 1 1 calc R
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'
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
C5 N1 C14 118.71(19)
C1 S1 C4 92.40(13)
C2 C1 S1 111.6(2)
C1 C2 C3 113.1(2)
C4 C3 C2 113.0(2)
C3 C4 C5 132.3(2)
C3 C4 S1 109.89(19)
C5 C4 S1 117.68(15)
N1 C5 C6 123.9(2)
N1 C5 C4 113.01(18)
C6 C5 C4 123.10(19)
C12 C6 C5 117.7(2)
C12 C6 C7 119.9(2)
C5 C6 C7 122.4(2)
C6 C7 C8 113.8(2)
C9 C8 C7 113.1(3)
C10 C9 C8 119.7(3)
C9 C10 C11 115.3(3)
C10 C11 C12 114.1(3)
C6 C12 C13 119.3(2)
C6 C12 C11 118.8(2)
C13 C12 C11 121.9(2)
C14 C13 C12 117.9(2)
C14 C13 C22 117.7(2)
C12 C13 C22 124.4(3)
N1 C14 C13 122.4(2)
N1 C14 C15 117.2(2)
C13 C14 C15 120.3(2)
C20 C15 C16 119.5(2)
C20 C15 C14 118.9(2)
C16 C15 C14 121.7(2)
C17 C16 C15 120.5(3)
C16 C17 C18 120.4(3)
C19 C18 C17 120.1(3)
C18 C19 C20 121.6(3)
C15 C20 C21 119.1(3)
C15 C20 C19 117.9(3)
C21 C20 C19 123.0(3)
C22 C21 C20 122.1(3)
C21 C22 C13 121.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.331(3)
N1 C14 1.348(3)
S1 C1 1.703(3)
S1 C4 1.719(2)
C1 C2 1.354(4)
C2 C3 1.397(4)
C3 C4 1.383(3)
C4 C5 1.482(3)
C5 C6 1.408(3)
C6 C12 1.393(3)
C6 C7 1.509(3)
C7 C8 1.530(4)
C8 C9 1.512(5)
C9 C10 1.471(5)
C10 C11 1.510(5)
C11 C12 1.512(4)
C12 C13 1.422(4)
C13 C14 1.411(3)
C13 C22 1.439(3)
C14 C15 1.461(3)
C15 C20 1.405(4)
C15 C16 1.409(4)
C16 C17 1.375(4)
C17 C18 1.388(5)
C18 C19 1.359(6)
C19 C20 1.424(5)
C20 C21 1.423(5)
C21 C22 1.335(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095652
