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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/4/03/31/4033107.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_4033107
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            'C28 H31 N'
_chemical_formula_weight         381.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                77.834(7)
_cell_angle_beta                 86.634(7)
_cell_angle_gamma                71.187(7)
_cell_formula_units_Z            2
_cell_length_a                   10.2452(8)
_cell_length_b                   10.4468(8)
_cell_length_c                   10.9779(9)
_cell_measurement_reflns_used    5636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.992
_cell_measurement_theta_min      0.983
_cell_volume                     1087.16(16)
_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      293(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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8376
_diffrn_reflns_theta_full        28.94
_diffrn_reflns_theta_max         28.94
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+0.3680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1841
_reflns_number_gt                2944
_reflns_number_total             5636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02159_si_002.cif
_cod_data_source_block           exp_2669_compound_18
_cod_depositor_comments
'Adding full bibliography for 4033102--4033107.cif.'
_cod_original_cell_volume        1087.15(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4033107
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.6558(2) 0.7836(2) 0.93886(18) 0.0536(5) Uani 1 1 d .
H1 H 0.6057 0.8570 0.9632 0.064 Uiso 1 1 calc R
C11 C 0.8292(2) 0.5485(2) 0.86377(19) 0.0385(5) Uani 1 1 d .
C16 C 0.8088(2) 0.5473(2) 1.00140(18) 0.0371(5) Uani 1 1 d .
H16 H 0.8777 0.5828 1.0280 0.045 Uiso 1 1 calc R
C14 C 0.7727(2) 0.3133(2) 1.02075(19) 0.0391(5) Uani 1 1 d .
H14 H 0.6754 0.3660 1.0022 0.047 Uiso 1 1 calc R
C18 C 0.6370(2) 0.6681(2) 1.1529(2) 0.0427(5) Uani 1 1 d .
C15 C 0.8319(2) 0.4021(2) 1.08038(19) 0.0411(5) Uani 1 1 d .
H15A H 0.9302 0.3564 1.0939 0.049 Uiso 1 1 calc R
H15B H 0.7898 0.4099 1.1611 0.049 Uiso 1 1 calc R
C25 C 0.7754(2) 0.1739(2) 1.1073(2) 0.0460(6) Uani 1 1 d .
C9 C 0.8924(2) 0.7111(2) 0.67467(19) 0.0435(5) Uani 1 1 d .
C17 C 0.6662(2) 0.6495(2) 1.0193(2) 0.0421(5) Uani 1 1 d .
H17 H 0.5959 0.6159 0.9926 0.051 Uiso 1 1 calc R
C1 C 0.7220(2) 0.7986(2) 0.8261(2) 0.0448(6) Uani 1 1 d .
C10 C 0.8156(2) 0.6871(2) 0.78595(19) 0.0402(5) Uani 1 1 d .
C4 C 0.8595(3) 0.8477(3) 0.6004(2) 0.0490(6) Uani 1 1 d .
C12 C 0.8448(2) 0.4349(2) 0.8186(2) 0.0462(6) Uani 1 1 d .
H12 H 0.8577 0.4409 0.7333 0.055 Uiso 1 1 calc R
C13 C 0.8429(3) 0.2987(2) 0.8957(2) 0.0467(6) Uani 1 1 d .
H13B H 0.9369 0.2373 0.9103 0.056 Uiso 1 1 calc R
H13A H 0.7948 0.2573 0.8499 0.056 Uiso 1 1 calc R
C8 C 1.0050(3) 0.6081(3) 0.6358(2) 0.0504(6) Uani 1 1 d .
H8 H 1.0301 0.5186 0.6830 0.060 Uiso 1 1 calc R
C23 C 0.7132(3) 0.7257(3) 1.2118(2) 0.0527(6) Uani 1 1 d .
H23 H 0.7833 0.7539 1.1685 0.063 Uiso 1 1 calc R
C19 C 0.5347(2) 0.6262(3) 1.2209(2) 0.0516(6) Uani 1 1 d .
H19 H 0.4828 0.5855 1.1846 0.062 Uiso 1 1 calc R
C21 C 0.5834(3) 0.7025(3) 1.4008(2) 0.0563(7) Uani 1 1 d .
C3 C 0.7557(3) 0.9560(3) 0.6409(2) 0.0574(7) Uani 1 1 d .
H3 H 0.7313 1.0442 0.5912 0.069 Uiso 1 1 calc R
C20 C 0.5086(3) 0.6443(3) 1.3429(2) 0.0584(7) Uani 1 1 d .
H20 H 0.4386 0.6162 1.3864 0.070 Uiso 1 1 calc R
C27 C 0.9209(3) 0.0888(3) 1.1567(2) 0.0615(7) Uani 1 1 d .
H27B H 0.9834 0.0787 1.0881 0.092 Uiso 1 1 calc R
H27C H 0.9208 -0.0007 1.2012 0.092 Uiso 1 1 calc R
H27A H 0.9497 0.1351 1.2117 0.092 Uiso 1 1 calc R
C2 C 0.6905(3) 0.9341(3) 0.7509(2) 0.0551(7) Uani 1 1 d .
H2 H 0.6250 1.0078 0.7774 0.066 Uiso 1 1 calc R
C6 C 1.0406(3) 0.7699(3) 0.4556(2) 0.0681(8) Uani 1 1 d .
H6 H 1.0882 0.7879 0.3827 0.082 Uiso 1 1 calc R
C28 C 0.7219(3) 0.0898(3) 1.0354(2) 0.0587(7) Uani 1 1 d .
H28C H 0.6377 0.1477 0.9927 0.088 Uiso 1 1 calc R
H28B H 0.7050 0.0137 1.0926 0.088 Uiso 1 1 calc R
H28A H 0.7895 0.0553 0.9759 0.088 Uiso 1 1 calc R
C26 C 0.6800(3) 0.2016(3) 1.2185(2) 0.0651(8) Uani 1 1 d .
H26C H 0.7163 0.2469 1.2693 0.098 Uiso 1 1 calc R
H26A H 0.6745 0.1157 1.2671 0.098 Uiso 1 1 calc R
H26B H 0.5897 0.2596 1.1886 0.098 Uiso 1 1 calc R
C7 C 1.0779(3) 0.6365(3) 0.5305(2) 0.0621(7) Uani 1 1 d .
H7 H 1.1526 0.5670 0.5085 0.074 Uiso 1 1 calc R
C5 C 0.9346(3) 0.8721(3) 0.4904(2) 0.0622(8) Uani 1 1 d .
H5 H 0.9108 0.9604 0.4408 0.075 Uiso 1 1 calc R
C22 C 0.6876(3) 0.7423(3) 1.3334(2) 0.0594(7) Uani 1 1 d .
H22 H 0.7410 0.7807 1.3707 0.071 Uiso 1 1 calc R
C24 C 0.5545(3) 0.7215(4) 1.5337(3) 0.0844(10) Uani 1 1 d .
H24C H 0.4682 0.7070 1.5593 0.127 Uiso 1 1 calc R
H24A H 0.5498 0.8135 1.5388 0.127 Uiso 1 1 calc R
H24B H 0.6271 0.6561 1.5874 0.127 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C17 123.6(2)
C12 C11 C10 124.6(2)
C12 C11 C16 121.1(2)
C10 C11 C16 114.05(19)
C11 C16 C15 113.02(18)
C11 C16 C17 108.33(16)
C15 C16 C17 113.51(17)
C15 C14 C13 108.24(18)
C15 C14 C25 114.12(17)
C13 C14 C25 114.22(19)
C19 C18 C23 117.5(2)
C19 C18 C17 121.3(2)
C23 C18 C17 121.2(2)
C14 C15 C16 113.26(16)
C27 C25 C28 109.1(2)
C27 C25 C26 108.7(2)
C28 C25 C26 107.9(2)
C27 C25 C14 111.79(19)
C28 C25 C14 109.53(18)
C26 C25 C14 109.6(2)
C8 C9 C4 117.0(2)
C8 C9 C10 123.8(2)
C4 C9 C10 119.1(2)
N1 C17 C18 109.17(19)
N1 C17 C16 108.54(18)
C18 C17 C16 113.92(17)
N1 C1 C10 121.9(2)
N1 C1 C2 117.6(2)
C10 C1 C2 120.6(2)
C1 C10 C9 119.2(2)
C1 C10 C11 116.3(2)
C9 C10 C11 124.4(2)
C3 C4 C5 121.5(2)
C3 C4 C9 119.0(2)
C5 C4 C9 119.5(3)
C11 C12 C13 124.7(2)
C12 C13 C14 112.28(19)
C7 C8 C9 121.9(2)
C22 C23 C18 121.5(2)
C18 C19 C20 120.7(2)
C20 C21 C22 117.5(2)
C20 C21 C24 121.4(3)
C22 C21 C24 121.1(3)
C2 C3 C4 121.4(2)
C21 C20 C19 121.8(2)
C3 C2 C1 120.3(3)
C5 C6 C7 119.6(3)
C8 C7 C6 120.4(3)
C6 C5 C4 121.6(3)
C23 C22 C21 121.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.381(3)
N1 C17 1.465(3)
C11 C12 1.341(3)
C11 C10 1.486(3)
C11 C16 1.511(3)
C16 C15 1.532(3)
C16 C17 1.536(3)
C14 C15 1.525(3)
C14 C13 1.525(3)
C14 C25 1.555(3)
C18 C19 1.383(3)
C18 C23 1.384(3)
C18 C17 1.520(3)
C25 C27 1.530(3)
C25 C28 1.533(3)
C25 C26 1.534(3)
C9 C8 1.416(3)
C9 C4 1.431(3)
C9 C10 1.435(3)
C1 C10 1.384(3)
C1 C2 1.425(3)
C4 C3 1.410(4)
C4 C5 1.415(3)
C12 C13 1.500(3)
C8 C7 1.371(3)
C23 C22 1.382(3)
C19 C20 1.390(3)
C21 C20 1.372(4)
C21 C22 1.387(4)
C21 C24 1.513(4)
C3 C2 1.359(4)
C6 C5 1.357(4)
C6 C7 1.405(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095655
