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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/67/7106721.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_7106721
loop_
_publ_author_name
'Xiaolin Pan'
'Yong Luo'
'Jie Wu'
_publ_section_title
;
 An unexpected palladium-catalyzed reaction of 2-alkynylhalobenzene with
 2-alkynylaniline: A novel and efficient route to
 11H-indeno[1,2-c]quinolin-11-ols
;
_journal_name_full               Chem.Commun.
_journal_page_first              8967
_journal_paper_doi               10.1039/c1cc12747k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C28 H21 N O2'
_chemical_formula_weight         403.46
_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                96.904(4)
_cell_angle_beta                 97.533(4)
_cell_angle_gamma                113.838(4)
_cell_formula_units_Z            2
_cell_length_a                   10.189(3)
_cell_length_b                   10.561(3)
_cell_length_c                   10.740(3)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.111
_cell_measurement_theta_min      2.344
_cell_volume                     1028.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4314
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0722
_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)+(0.1778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2207
_reflns_number_gt                2838
_reflns_number_total             3576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12747k.txt
_cod_data_source_block           a01124b
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106721
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48301(15) 0.18508(14) 0.08715(13) 0.0456(4) Uani 1 1 d . . .
H1 H 0.4089 0.1071 0.0458 0.068 Uiso 1 1 d R . .
N1 N 0.02836(18) 0.21582(17) 0.18114(16) 0.0447(5) Uani 1 1 d . . .
C1 C 0.4470(2) 0.2014(2) 0.21013(18) 0.0392(5) Uani 1 1 d . . .
C2 C 0.3069(2) 0.22312(19) 0.19672(17) 0.0366(5) Uani 1 1 d . . .
C3 C 0.2831(2) 0.33687(19) 0.15889(17) 0.0377(5) Uani 1 1 d . . .
C4 C 0.3909(2) 0.4567(2) 0.12929(19) 0.0437(5) Uani 1 1 d . . .
H4 H 0.4846 0.4626 0.1303 0.052 Uiso 1 1 calc R . .
C5 C 0.3593(3) 0.5644(2) 0.0991(2) 0.0506(6) Uani 1 1 d . . .
H5 H 0.4318 0.6439 0.0809 0.061 Uiso 1 1 calc R . .
C6 C 0.2183(3) 0.5554(2) 0.0957(2) 0.0544(6) Uani 1 1 d . . .
H6 H 0.1978 0.6296 0.0753 0.065 Uiso 1 1 calc R . .
C7 C 0.1115(2) 0.4412(2) 0.1214(2) 0.0505(6) Uani 1 1 d . . .
H7 H 0.0179 0.4368 0.1171 0.061 Uiso 1 1 calc R . .
C8 C 0.1398(2) 0.3278(2) 0.15482(18) 0.0407(5) Uani 1 1 d . . .
C9 C 0.0552(2) 0.1114(2) 0.21673(18) 0.0415(5) Uani 1 1 d . . .
C10 C 0.1955(2) 0.11339(19) 0.22745(17) 0.0386(5) Uani 1 1 d . . .
C11 C 0.2509(2) 0.01323(19) 0.27068(18) 0.0406(5) Uani 1 1 d . . .
C12 C 0.1864(3) -0.1086(2) 0.3186(2) 0.0511(6) Uani 1 1 d . . .
H12 H 0.0885 -0.1433 0.3256 0.061 Uiso 1 1 calc R . .
C13 C 0.2711(3) -0.1774(2) 0.3557(2) 0.0597(6) Uani 1 1 d . . .
H13 H 0.2301 -0.2583 0.3898 0.072 Uiso 1 1 calc R . .
C14 C 0.4143(3) -0.1278(2) 0.3429(3) 0.0628(7) Uani 1 1 d . . .
H14 H 0.4680 -0.1775 0.3660 0.075 Uiso 1 1 calc R . .
C15 C 0.4804(3) -0.0065(2) 0.2968(2) 0.0531(6) Uani 1 1 d . . .
H15 H 0.5782 0.0272 0.2897 0.064 Uiso 1 1 calc R . .
C16 C 0.3978(2) 0.0643(2) 0.26111(18) 0.0419(5) Uani 1 1 d . . .
C17 C 0.5753(2) 0.31891(19) 0.30411(19) 0.0414(5) Uani 1 1 d . . .
C18 C 0.5568(2) 0.3608(2) 0.4254(2) 0.0497(6) Uani 1 1 d . . .
H18 H 0.4651 0.3204 0.4466 0.060 Uiso 1 1 calc R . .
C19 C 0.6728(3) 0.4614(2) 0.5146(2) 0.0604(7) Uani 1 1 d . . .
H19 H 0.6585 0.4884 0.5955 0.072 Uiso 1 1 calc R . .
C20 C 0.8084(3) 0.5223(3) 0.4860(3) 0.0680(8) Uani 1 1 d . . .
H20 H 0.8867 0.5898 0.5470 0.082 Uiso 1 1 calc R . .
C21 C 0.8278(3) 0.4827(3) 0.3663(3) 0.0740(8) Uani 1 1 d . . .
H21 H 0.9199 0.5246 0.3461 0.089 Uiso 1 1 calc R . .
C22 C 0.7125(2) 0.3813(2) 0.2746(2) 0.0583(6) Uani 1 1 d . . .
H22 H 0.7274 0.3554 0.1937 0.070 Uiso 1 1 calc R . .
C23 C -0.0681(2) -0.0089(2) 0.24487(19) 0.0432(5) Uani 1 1 d . . .
C24 C -0.1187(3) 0.0023(2) 0.3562(2) 0.0539(6) Uani 1 1 d . . .
H24 H -0.0818 0.0891 0.4113 0.065 Uiso 1 1 calc R . .
C25 C -0.2236(3) -0.1141(3) 0.3864(2) 0.0631(7) Uani 1 1 d . . .
H25 H -0.2562 -0.1056 0.4626 0.076 Uiso 1 1 calc R . .
C26 C -0.2807(3) -0.2420(3) 0.3062(2) 0.0600(6) Uani 1 1 d . . .
H26 H -0.3504 -0.3209 0.3279 0.072 Uiso 1 1 calc R . .
C27 C -0.2342(3) -0.2528(3) 0.1934(2) 0.0679(7) Uani 1 1 d . . .
H27 H -0.2754 -0.3387 0.1364 0.082 Uiso 1 1 calc R . .
C28 C -0.1278(3) -0.1382(2) 0.1636(2) 0.0627(7) Uani 1 1 d . . .
H28 H -0.0951 -0.1475 0.0876 0.075 Uiso 1 1 calc R . .
O2 O 0.7083(2) 0.0979(2) 0.0531(2) 0.0880(7) Uani 1 1 d . . .
H2A H 0.7931 0.1353 0.0969 0.132 Uiso 1 1 d R . .
H2B H 0.6503 0.0944 0.1026 0.132 Uiso 1 1 d 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'
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
C1 O1 H1 102.6 . . ?
C9 N1 C8 118.70(18) . . ?
O1 C1 C17 110.65(16) . . ?
O1 C1 C16 111.90(15) . . ?
C17 C1 C16 110.66(15) . . ?
O1 C1 C2 109.13(15) . . ?
C17 C1 C2 113.48(16) . . ?
C16 C1 C2 100.69(15) . . ?
C10 C2 C3 120.12(18) . . ?
C10 C2 C1 111.18(16) . . ?
C3 C2 C1 128.70(17) . . ?
C4 C3 C2 124.70(18) . . ?
C4 C3 C8 119.24(18) . . ?
C2 C3 C8 116.03(18) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C8 C7 118.35(18) . . ?
N1 C8 C3 123.40(18) . . ?
C7 C8 C3 118.25(19) . . ?
N1 C9 C10 121.84(19) . . ?
N1 C9 C23 117.47(18) . . ?
C10 C9 C23 120.69(18) . . ?
C2 C10 C9 119.83(18) . . ?
C2 C10 C11 109.37(17) . . ?
C9 C10 C11 130.80(18) . . ?
C12 C11 C16 120.14(19) . . ?
C12 C11 C10 132.41(19) . . ?
C16 C11 C10 107.40(16) . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118.2(2) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C15 C16 C11 120.88(19) . . ?
C15 C16 C1 127.85(19) . . ?
C11 C16 C1 111.27(17) . . ?
C22 C17 C18 118.6(2) . . ?
C22 C17 C1 121.99(19) . . ?
C18 C17 C1 119.34(18) . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 119.7(2) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C28 118.4(2) . . ?
C24 C23 C9 121.15(19) . . ?
C28 C23 C9 120.3(2) . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.8(2) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.1(2) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
H2A O2 H2B 107.8 . . ?
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
O1 C1 1.426(2) . ?
O1 H1 0.8756 . ?
N1 C9 1.325(3) . ?
N1 C8 1.359(3) . ?
C1 C17 1.520(3) . ?
C1 C16 1.524(3) . ?
C1 C2 1.527(3) . ?
C2 C10 1.366(3) . ?
C2 C3 1.412(3) . ?
C3 C4 1.405(3) . ?
C3 C8 1.418(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.346(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.410(3) . ?
C9 C23 1.478(3) . ?
C10 C11 1.478(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C17 C22 1.382(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.374(3) . ?
C23 C28 1.378(3) . ?
C24 C25 1.373(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.366(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O2 H2A 0.8344 . ?
O2 H2B 0.8387 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182040
