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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/4/03/31/4033106.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_4033106
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            'C40 H40 Cl N O2'
_chemical_formula_weight         602.18
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.222(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3419(7)
_cell_length_b                   15.3072(12)
_cell_length_c                   14.5765(14)
_cell_measurement_reflns_used    8410
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.972
_cell_measurement_theta_min      0.951
_cell_volume                     1638.2(3)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10136
_diffrn_reflns_theta_full        36.98
_diffrn_reflns_theta_max         36.98
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         8410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0448
_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)+(0.0573P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                4097
_reflns_number_total             8410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02159_si_002.cif
_cod_data_source_block           gattu_compound_14b
_cod_depositor_comments
'Adding full bibliography for 4033102--4033107.cif.'
_cod_original_cell_volume        1638.2(2)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4033106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl -0.0908(3) 0.51524(10) 1.01207(8) 0.1211(7) Uani 1 1 d .
N1 N 0.0448(4) 0.6954(2) 0.6008(2) 0.0484(9) Uani 1 1 d .
O1 O 0.7894(4) 0.22681(16) -0.08747(18) 0.0597(8) Uani 1 1 d .
C30 C 0.1456(5) 0.6344(2) 0.6392(2) 0.0462(10) Uani 1 1 d .
C4 C 0.6091(5) 0.3464(2) 0.1686(2) 0.0394(9) Uani 1 1 d .
C9 C 0.7233(4) 0.4269(2) 0.3118(2) 0.0367(9) Uani 1 1 d .
H9 H 0.6926 0.3755 0.3487 0.044 Uiso 1 1 calc R
C14 C 0.6970(4) 0.5090(2) 0.3701(2) 0.0382(8) Uani 1 1 d .
H14 H 0.7177 0.5581 0.3282 0.046 Uiso 1 1 calc R
C34 C -0.0288(8) 0.5441(3) 0.9010(3) 0.0753(16) Uani 1 1 d .
C17 C 0.5253(5) 0.5931(2) 0.4732(2) 0.0389(9) Uani 1 1 d .
O2 O 1.0528(5) 0.2954(2) -0.1184(2) 0.0818(11) Uani 1 1 d .
C18 C 0.3660(5) 0.6399(2) 0.5149(2) 0.0403(9) Uani 1 1 d .
C13 C 0.4989(4) 0.5197(2) 0.4034(2) 0.0368(8) Uani 1 1 d .
C3 C 0.8094(5) 0.3269(2) 0.1499(2) 0.0422(9) Uani 1 1 d .
C31 C 0.0836(5) 0.5997(2) 0.7290(2) 0.0503(10) Uani 1 1 d .
C22 C 0.5405(6) 0.8121(3) 0.2830(3) 0.0638(13) Uani 1 1 d .
H22 H 0.6550 0.8071 0.2564 0.077 Uiso 1 1 calc R
C20 C 0.3213(5) 0.7640(2) 0.3972(2) 0.0464(10) Uani 1 1 d .
C29 C 0.3055(5) 0.6038(2) 0.5964(2) 0.0461(9) Uani 1 1 d .
H29 H 0.3714 0.5587 0.6235 0.055 Uiso 1 1 calc R
C16 C 0.6947(5) 0.5939(2) 0.5037(2) 0.0454(10) Uani 1 1 d .
H16 H 0.7359 0.6306 0.5502 0.054 Uiso 1 1 calc R
C8 C 0.9217(4) 0.4195(2) 0.2808(2) 0.0441(9) Uani 1 1 d .
H8A H 0.9665 0.4770 0.2643 0.053 Uiso 1 1 calc R
H8B H 0.9954 0.3979 0.3313 0.053 Uiso 1 1 calc R
C25 C 0.1998(6) 0.8274(2) 0.3628(3) 0.0509(10) Uani 1 1 d .
C10 C 0.5969(4) 0.4303(2) 0.2284(2) 0.0390(9) Uani 1 1 d .
H10 H 0.6435 0.4778 0.1899 0.047 Uiso 1 1 calc R
C36 C -0.0840(6) 0.6247(3) 0.7638(3) 0.0670(13) Uani 1 1 d .
H36 H -0.1601 0.6607 0.7294 0.080 Uiso 1 1 calc R
C19 C 0.2676(5) 0.7115(2) 0.4762(2) 0.0421(9) Uani 1 1 d .
C7 C 0.9419(5) 0.3591(2) 0.2000(3) 0.0465(10) Uani 1 1 d .
H7 H 1.0598 0.3431 0.1841 0.056 Uiso 1 1 calc R
C28 C 0.1019(5) 0.7318(2) 0.5207(3) 0.0445(10) Uani 1 1 d .
C32 C 0.1863(7) 0.5439(3) 0.7805(3) 0.0730(15) Uani 1 1 d .
H32 H 0.2958 0.5238 0.7566 0.088 Uiso 1 1 calc R
C11 C 0.3976(5) 0.4559(2) 0.2517(3) 0.0482(10) Uani 1 1 d .
H11A H 0.3343 0.4704 0.1952 0.058 Uiso 1 1 calc R
H11B H 0.3372 0.4057 0.2784 0.058 Uiso 1 1 calc R
C37 C 0.5227(5) 0.2675(2) 0.2179(3) 0.0547(11) Uani 1 1 d .
H37C H 0.5495 0.2150 0.1844 0.082 Uiso 1 1 calc R
H37B H 0.3932 0.2753 0.2210 0.082 Uiso 1 1 calc R
H37A H 0.5718 0.2630 0.2788 0.082 Uiso 1 1 calc R
C24 C 0.2498(7) 0.8804(3) 0.2880(3) 0.0633(12) Uani 1 1 d .
H24 H 0.1672 0.9212 0.2653 0.076 Uiso 1 1 calc R
C38 C 0.4304(5) 0.4396(2) 0.4582(3) 0.0543(11) Uani 1 1 d .
H38C H 0.4247 0.3896 0.4185 0.081 Uiso 1 1 calc R
H38B H 0.3112 0.4516 0.4820 0.081 Uiso 1 1 calc R
H38A H 0.5126 0.4279 0.5080 0.081 Uiso 1 1 calc R
C1 C 0.7523(5) 0.2915(2) -0.0153(2) 0.0519(11) Uani 1 1 d .
H1 H 0.7929 0.3494 -0.0352 0.062 Uiso 1 1 calc R
C21 C 0.4957(5) 0.7594(2) 0.3560(2) 0.0533(11) Uani 1 1 d .
H21 H 0.5813 0.7201 0.3788 0.064 Uiso 1 1 calc R
C23 C 0.4162(7) 0.8731(3) 0.2484(3) 0.0695(14) Uani 1 1 d .
H23 H 0.4471 0.9082 0.1988 0.083 Uiso 1 1 calc R
C15 C 0.8148(5) 0.5284(3) 0.4545(2) 0.0488(10) Uani 1 1 d .
H15B H 0.8351 0.4765 0.4912 0.059 Uiso 1 1 calc R
H15A H 0.9311 0.5537 0.4376 0.059 Uiso 1 1 calc R
C33 C 0.1344(8) 0.5157(3) 0.8678(3) 0.0870(17) Uani 1 1 d .
H33 H 0.2086 0.4787 0.9021 0.104 Uiso 1 1 calc R
C12 C 0.3802(5) 0.5337(2) 0.3185(2) 0.0464(10) Uani 1 1 d .
H12B H 0.4170 0.5870 0.2878 0.056 Uiso 1 1 calc R
H12A H 0.2541 0.5401 0.3369 0.056 Uiso 1 1 calc R
C39 C 0.9492(7) 0.2367(3) -0.1320(3) 0.0614(12) Uani 1 1 d .
C27 C -0.0211(5) 0.7943(2) 0.4810(3) 0.0534(11) Uani 1 1 d .
H27 H -0.1338 0.8040 0.5081 0.064 Uiso 1 1 calc R
C5 C 0.5094(5) 0.3612(3) 0.0757(3) 0.0523(10) Uani 1 1 d .
H5A H 0.3792 0.3622 0.0869 0.063 Uiso 1 1 calc R
H5B H 0.5435 0.4182 0.0522 0.063 Uiso 1 1 calc R
C2 C 0.8512(5) 0.2654(2) 0.0716(2) 0.0513(10) Uani 1 1 d .
H2B H 0.9814 0.2653 0.0604 0.062 Uiso 1 1 calc R
H2A H 0.8157 0.2066 0.0885 0.062 Uiso 1 1 calc R
C6 C 0.5490(6) 0.2924(3) 0.0016(3) 0.0606(12) Uani 1 1 d .
H6A H 0.5087 0.2353 0.0220 0.073 Uiso 1 1 calc R
H6B H 0.4844 0.3068 -0.0546 0.073 Uiso 1 1 calc R
C26 C 0.0249(6) 0.8393(2) 0.4047(3) 0.0596(11) Uani 1 1 d .
H26 H -0.0578 0.8784 0.3790 0.072 Uiso 1 1 calc R
C35 C -0.1391(7) 0.5963(3) 0.8503(3) 0.0766(15) Uani 1 1 d .
H35 H -0.2518 0.6131 0.8732 0.092 Uiso 1 1 calc R
C40 C 0.9745(7) 0.1657(3) -0.2018(3) 0.0782(16) Uani 1 1 d .
H40C H 0.9309 0.1114 -0.1773 0.117 Uiso 1 1 calc R
H40B H 1.1014 0.1604 -0.2163 0.117 Uiso 1 1 calc R
H40A H 0.9072 0.1799 -0.2564 0.117 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C30 N1 C28 118.8(3)
C39 O1 C1 115.6(3)
N1 C30 C29 121.0(3)
N1 C30 C31 117.1(3)
C29 C30 C31 122.0(4)
C3 C4 C37 109.1(3)
C3 C4 C5 109.0(3)
C37 C4 C5 109.1(3)
C3 C4 C10 108.6(3)
C37 C4 C10 111.2(2)
C5 C4 C10 109.9(3)
C10 C9 C14 109.6(3)
C10 C9 C8 110.1(2)
C14 C9 C8 110.3(3)
C15 C14 C9 122.3(3)
C15 C14 C13 104.9(2)
C9 C14 C13 112.5(3)
C35 C34 C33 121.1(4)
C35 C34 Cl1 120.0(4)
C33 C34 Cl1 118.9(5)
C16 C17 C18 126.4(3)
C16 C17 C13 110.4(3)
C18 C17 C13 121.5(3)
C29 C18 C19 118.8(3)
C29 C18 C17 114.2(3)
C19 C18 C17 126.9(3)
C12 C13 C17 120.5(3)
C12 C13 C14 107.2(2)
C17 C13 C14 99.8(3)
C12 C13 C38 110.1(3)
C17 C13 C38 106.2(2)
C14 C13 C38 112.8(3)
C7 C3 C2 120.2(3)
C7 C3 C4 122.8(3)
C2 C3 C4 117.0(4)
C32 C31 C36 117.4(4)
C32 C31 C30 122.6(3)
C36 C31 C30 120.0(4)
C21 C22 C23 120.8(4)
C25 C20 C21 117.0(3)
C25 C20 C19 119.2(3)
C21 C20 C19 123.6(4)
C18 C29 C30 121.1(4)
C17 C16 C15 112.5(3)
C7 C8 C9 111.9(3)
C24 C25 C20 120.4(4)
C24 C25 C26 119.5(4)
C20 C25 C26 120.1(3)
C9 C10 C11 113.9(3)
C9 C10 C4 112.4(3)
C11 C10 C4 112.8(3)
C31 C36 C35 120.4(5)
C28 C19 C18 115.0(3)
C28 C19 C20 118.4(3)
C18 C19 C20 126.6(3)
C3 C7 C8 126.3(3)
N1 C28 C19 124.8(4)
N1 C28 C27 115.1(3)
C19 C28 C27 120.1(3)
C31 C32 C33 122.9(4)
C12 C11 C10 114.4(3)
C23 C24 C25 121.3(4)
O1 C1 C2 109.4(3)
O1 C1 C6 107.9(3)
C2 C1 C6 109.7(3)
C22 C21 C20 121.2(4)
C24 C23 C22 119.3(4)
C16 C15 C14 100.4(3)
C34 C33 C32 117.9(5)
C13 C12 C11 110.7(3)
O2 C39 O1 123.9(3)
O2 C39 C40 125.3(4)
O1 C39 C40 110.8(4)
C26 C27 C28 120.8(3)
C6 C5 C4 115.0(3)
C1 C2 C3 111.7(3)
C1 C6 C5 108.1(3)
C27 C26 C25 120.8(4)
C34 C35 C36 120.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C34 1.740(4)
N1 C30 1.315(5)
N1 C28 1.361(4)
O1 C39 1.352(5)
O1 C1 1.471(4)
C30 C29 1.411(4)
C30 C31 1.485(5)
C4 C3 1.526(5)
C4 C37 1.543(5)
C4 C5 1.553(5)
C4 C10 1.555(4)
C9 C10 1.527(5)
C9 C14 1.530(4)
C9 C8 1.531(4)
C14 C15 1.530(5)
C14 C13 1.544(4)
C34 C35 1.355(7)
C34 C33 1.365(6)
C17 C16 1.319(5)
C17 C18 1.502(4)
C17 C13 1.528(5)
O2 C39 1.194(5)
C18 C29 1.386(4)
C18 C19 1.428(5)
C13 C12 1.525(5)
C13 C38 1.548(4)
C3 C7 1.310(5)
C3 C2 1.513(5)
C31 C32 1.363(6)
C31 C36 1.387(5)
C22 C21 1.376(5)
C22 C23 1.398(6)
C20 C25 1.410(5)
C20 C21 1.418(5)
C20 C19 1.459(5)
C16 C15 1.518(4)
C8 C7 1.503(5)
C25 C24 1.408(5)
C25 C26 1.436(5)
C10 C11 1.554(4)
C36 C35 1.394(6)
C19 C28 1.416(4)
C28 C27 1.436(5)
C32 C33 1.398(5)
C11 C12 1.544(4)
C24 C23 1.358(6)
C1 C2 1.511(5)
C1 C6 1.514(5)
C39 C40 1.500(5)
C27 C26 1.352(5)
C5 C6 1.538(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095654
