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#$Date: 2020-07-07 02:21:35 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038554.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_4038554
loop_
_publ_author_name
'Chakraborty, Baitan'
'Kar, Abhishek'
'Chanda, Rupsa'
'Jana, Umasish'
_publ_section_title
;
 Application of Povarov Reaction in Biaryls under Iron Catalysis for the
 General Synthesis of Dibenzo[a, c]acridines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01300
_journal_year                    2020
_chemical_formula_sum            'C29 H21 N'
_chemical_formula_weight         383.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 106.121(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4336(13)
_cell_length_b                   19.646(3)
_cell_length_c                   10.9945(14)
_cell_measurement_reflns_used    4502
_cell_measurement_temperature    152(2)
_cell_measurement_theta_max      25.6687
_cell_measurement_theta_min      2.4750
_cell_volume                     1957.5(5)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      152(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  multi-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1679
_diffrn_reflns_av_unetI/netI     0.1228
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19427
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.749
_diffrn_reflns_theta_min         2.189
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0870
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01300_si_002.cif
_cod_data_source_block           mo_BROC020919_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038554
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4479(2) 0.38174(11) 0.36303(17) 0.0325(5) Uani 1 1 d . . . . .
C1 C -0.0120(3) 0.39600(15) 0.0255(3) 0.0496(8) Uani 1 1 d . . . . .
H3 H -0.015631 0.440871 0.063442 0.074 Uiso 1 1 calc R U . . .
H1 H -0.103238 0.371132 0.021507 0.074 Uiso 1 1 calc R U . . .
H21 H -0.001665 0.401574 -0.060210 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1180(3) 0.35664(14) 0.1051(2) 0.0364(6) Uani 1 1 d . . . . .
C3 C 0.2222(3) 0.38571(13) 0.2017(2) 0.0344(6) Uani 1 1 d . . . . .
H14 H 0.215668 0.432826 0.218803 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3408(3) 0.34678(12) 0.2775(2) 0.0303(6) Uani 1 1 d . . . . .
C5 C 0.5558(3) 0.34691(12) 0.4418(2) 0.0297(6) Uani 1 1 d . . . . .
C6 C 0.6831(3) 0.38642(13) 0.5151(2) 0.0322(6) Uani 1 1 d . . . . .
C7 C 0.8024(3) 0.35314(13) 0.5986(2) 0.0321(6) Uani 1 1 d . . . . .
C8 C 0.7859(3) 0.28133(13) 0.6308(2) 0.0315(6) Uani 1 1 d . . . . .
C9 C 0.8869(3) 0.25090(14) 0.7348(2) 0.0387(7) Uani 1 1 d . . . . .
H11 H 0.973827 0.275115 0.776883 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8642(3) 0.18706(14) 0.7779(2) 0.0429(7) Uani 1 1 d . . . . .
H2 H 0.935107 0.167311 0.847797 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1380(3) 0.28759(13) 0.0767(2) 0.0361(6) Uani 1 1 d . . . . .
H20 H 0.069600 0.268110 0.004994 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2496(3) 0.24698(13) 0.1461(2) 0.0316(6) Uani 1 1 d . . . . .
C13 C 0.2640(3) 0.17748(13) 0.0921(2) 0.0384(7) Uani 1 1 d . . . . .
H5 H 0.224580 0.142986 0.138334 0.058 Uiso 1 1 calc R U . . .
H6 H 0.368276 0.167904 0.100633 0.058 Uiso 1 1 calc R U . . .
H4 H 0.208529 0.176417 0.002436 0.058 Uiso 1 1 calc R U . . .
C14 C 0.3495(3) 0.27503(12) 0.2589(2) 0.0297(6) Uani 1 1 d . . . . .
C15 C 0.4555(3) 0.23871(13) 0.35465(19) 0.0277(6) Uani 1 1 d . . . . .
C16 C 0.5551(3) 0.27432(12) 0.4519(2) 0.0290(6) Uani 1 1 d . . . . .
C17 C 0.9296(3) 0.39137(14) 0.6563(2) 0.0415(7) Uani 1 1 d . . . . .
H7 H 1.012365 0.369512 0.711939 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9356(3) 0.46006(15) 0.6330(2) 0.0471(8) Uani 1 1 d . . . . .
H10 H 1.022933 0.484941 0.671340 0.056 Uiso 1 1 calc R U . . .
C19 C 0.8153(3) 0.49304(14) 0.5541(2) 0.0439(7) Uani 1 1 d . . . . .
H8 H 0.819001 0.540698 0.540652 0.053 Uiso 1 1 calc R U . . .
C20 C 0.6900(3) 0.45675(13) 0.4948(2) 0.0378(7) Uani 1 1 d . . . . .
H9 H 0.607892 0.479459 0.440030 0.045 Uiso 1 1 calc R U . . .
C21 C 0.7361(3) 0.15212(14) 0.7175(2) 0.0399(7) Uani 1 1 d . . . . .
H12 H 0.716861 0.108957 0.748527 0.048 Uiso 1 1 calc R U . . .
C22 C 0.6369(3) 0.17965(13) 0.6131(2) 0.0353(6) Uani 1 1 d . . . . .
H13 H 0.549948 0.154912 0.573163 0.042 Uiso 1 1 calc R U . . .
C23 C 0.6605(3) 0.24366(12) 0.5634(2) 0.0290(6) Uani 1 1 d . . . . .
C24 C 0.4616(3) 0.16299(12) 0.34873(19) 0.0295(6) Uani 1 1 d . . . . .
C25 C 0.5799(3) 0.13246(13) 0.3178(2) 0.0359(6) Uani 1 1 d . . . . .
H19 H 0.656336 0.159910 0.302933 0.043 Uiso 1 1 calc R U . . .
C26 C 0.5872(3) 0.06248(14) 0.3086(2) 0.0454(8) Uani 1 1 d . . . . .
H15 H 0.667208 0.042210 0.285153 0.054 Uiso 1 1 calc R U . . .
C27 C 0.4791(4) 0.02180(15) 0.3333(2) 0.0496(8) Uani 1 1 d . . . . .
H16 H 0.484709 -0.026324 0.327480 0.059 Uiso 1 1 calc R U . . .
C28 C 0.3628(4) 0.05182(14) 0.3665(2) 0.0472(8) Uani 1 1 d . . . . .
H17 H 0.288770 0.024110 0.384854 0.057 Uiso 1 1 calc R U . . .
C29 C 0.3531(3) 0.12216(13) 0.3733(2) 0.0376(6) Uani 1 1 d . . . . .
H18 H 0.271841 0.142345 0.394808 0.045 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 118.6(2) . . ?
C2 C1 H3 109.5 . . ?
C2 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C2 C1 H21 109.5 . . ?
H3 C1 H21 109.5 . . ?
H1 C1 H21 109.5 . . ?
C3 C2 C11 117.6(2) . . ?
C3 C2 C1 122.3(2) . . ?
C11 C2 C1 120.0(2) . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H14 119.5 . . ?
C4 C3 H14 119.5 . . ?
N1 C4 C3 116.6(2) . . ?
N1 C4 C14 122.4(2) . . ?
C3 C4 C14 121.0(2) . . ?
N1 C5 C16 123.0(2) . . ?
N1 C5 C6 116.6(2) . . ?
C16 C5 C6 120.3(2) . . ?
C7 C6 C20 120.0(2) . . ?
C7 C6 C5 119.9(2) . . ?
C20 C6 C5 120.0(2) . . ?
C6 C7 C17 118.4(2) . . ?
C6 C7 C8 119.0(2) . . ?
C17 C7 C8 122.4(2) . . ?
C9 C8 C23 118.8(2) . . ?
C9 C8 C7 120.7(2) . . ?
C23 C8 C7 120.2(2) . . ?
C10 C9 C8 122.2(2) . . ?
C10 C9 H11 118.9 . . ?
C8 C9 H11 118.9 . . ?
C9 C10 C21 118.9(2) . . ?
C9 C10 H2 120.6 . . ?
C21 C10 H2 120.6 . . ?
C12 C11 C2 124.3(2) . . ?
C12 C11 H20 117.8 . . ?
C2 C11 H20 117.8 . . ?
C11 C12 C14 118.2(2) . . ?
C11 C12 C13 116.5(2) . . ?
C14 C12 C13 125.1(2) . . ?
C12 C13 H5 109.5 . . ?
C12 C13 H6 109.5 . . ?
H5 C13 H6 109.5 . . ?
C12 C13 H4 109.5 . . ?
H5 C13 H4 109.5 . . ?
H6 C13 H4 109.5 . . ?
C15 C14 C4 116.4(2) . . ?
C15 C14 C12 126.9(2) . . ?
C4 C14 C12 116.7(2) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 C24 120.4(2) . . ?
C14 C15 C24 119.7(2) . . ?
C15 C16 C5 117.1(2) . . ?
C15 C16 C23 125.8(2) . . ?
C5 C16 C23 117.1(2) . . ?
C18 C17 C7 120.8(3) . . ?
C18 C17 H7 119.6 . . ?
C7 C17 H7 119.6 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H10 119.8 . . ?
C19 C18 H10 119.8 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H8 120.0 . . ?
C18 C19 H8 120.0 . . ?
C19 C20 C6 120.3(3) . . ?
C19 C20 H9 119.8 . . ?
C6 C20 H9 119.8 . . ?
C22 C21 C10 120.3(3) . . ?
C22 C21 H12 119.8 . . ?
C10 C21 H12 119.8 . . ?
C21 C22 C23 122.0(2) . . ?
C21 C22 H13 119.0 . . ?
C23 C22 H13 119.0 . . ?
C22 C23 C8 117.4(2) . . ?
C22 C23 C16 122.8(2) . . ?
C8 C23 C16 119.5(2) . . ?
C29 C24 C25 119.0(3) . . ?
C29 C24 C15 122.0(2) . . ?
C25 C24 C15 119.0(2) . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H19 119.8 . . ?
C24 C25 H19 119.8 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H15 119.8 . . ?
C25 C26 H15 119.8 . . ?
C26 C27 C28 119.3(3) . . ?
C26 C27 H16 120.4 . . ?
C28 C27 H16 120.4 . . ?
C27 C28 C29 120.5(3) . . ?
C27 C28 H17 119.7 . . ?
C29 C28 H17 119.7 . . ?
C24 C29 C28 120.2(3) . . ?
C24 C29 H18 119.9 . . ?
C28 C29 H18 119.9 . . ?
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
N1 C5 1.328(3) . ?
N1 C4 1.360(3) . ?
C1 C2 1.507(3) . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C1 H21 0.9800 . ?
C2 C3 1.357(3) . ?
C2 C11 1.416(4) . ?
C3 C4 1.419(3) . ?
C3 H14 0.9500 . ?
C4 C14 1.430(3) . ?
C5 C16 1.431(3) . ?
C5 C6 1.469(3) . ?
C6 C7 1.401(3) . ?
C6 C20 1.404(3) . ?
C7 C17 1.409(3) . ?
C7 C8 1.473(3) . ?
C8 C9 1.402(3) . ?
C8 C23 1.418(3) . ?
C9 C10 1.379(4) . ?
C9 H11 0.9500 . ?
C10 C21 1.388(4) . ?
C10 H2 0.9500 . ?
C11 C12 1.371(3) . ?
C11 H20 0.9500 . ?
C12 C14 1.443(3) . ?
C12 C13 1.510(3) . ?
C13 H5 0.9800 . ?
C13 H6 0.9800 . ?
C13 H4 0.9800 . ?
C14 C15 1.425(3) . ?
C15 C16 1.399(3) . ?
C15 C24 1.491(3) . ?
C16 C23 1.476(3) . ?
C17 C18 1.378(4) . ?
C17 H7 0.9500 . ?
C18 C19 1.383(4) . ?
C18 H10 0.9500 . ?
C19 C20 1.379(4) . ?
C19 H8 0.9500 . ?
C20 H9 0.9500 . ?
C21 C22 1.374(3) . ?
C21 H12 0.9500 . ?
C22 C23 1.413(3) . ?
C22 H13 0.9500 . ?
C24 C29 1.384(3) . ?
C24 C25 1.390(3) . ?
C25 C26 1.382(4) . ?
C25 H19 0.9500 . ?
C26 C27 1.380(4) . ?
C26 H15 0.9500 . ?
C27 C28 1.382(4) . ?
C27 H16 0.9500 . ?
C28 C29 1.388(4) . ?
C28 H17 0.9500 . ?
C29 H18 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C2 C3 C4 -4.7(4) . . . . ?
C1 C2 C3 C4 177.9(2) . . . . ?
C5 N1 C4 C3 175.5(2) . . . . ?
C5 N1 C4 C14 -7.8(3) . . . . ?
C2 C3 C4 N1 173.2(2) . . . . ?
C2 C3 C4 C14 -3.5(4) . . . . ?
C4 N1 C5 C16 -8.1(3) . . . . ?
C4 N1 C5 C6 168.58(19) . . . . ?
N1 C5 C6 C7 -179.0(2) . . . . ?
C16 C5 C6 C7 -2.2(3) . . . . ?
N1 C5 C6 C20 -3.5(3) . . . . ?
C16 C5 C6 C20 173.3(2) . . . . ?
C20 C6 C7 C17 -2.7(3) . . . . ?
C5 C6 C7 C17 172.8(2) . . . . ?
C20 C6 C7 C8 172.4(2) . . . . ?
C5 C6 C7 C8 -12.1(3) . . . . ?
C6 C7 C8 C9 -164.8(2) . . . . ?
C17 C7 C8 C9 10.1(3) . . . . ?
C6 C7 C8 C23 9.8(3) . . . . ?
C17 C7 C8 C23 -175.3(2) . . . . ?
C23 C8 C9 C10 -3.6(4) . . . . ?
C7 C8 C9 C10 171.0(2) . . . . ?
C8 C9 C10 C21 -1.0(4) . . . . ?
C3 C2 C11 C12 4.9(4) . . . . ?
C1 C2 C11 C12 -177.6(2) . . . . ?
C2 C11 C12 C14 3.2(4) . . . . ?
C2 C11 C12 C13 -172.7(2) . . . . ?
N1 C4 C14 C15 15.3(3) . . . . ?
C3 C4 C14 C15 -168.2(2) . . . . ?
N1 C4 C14 C12 -165.1(2) . . . . ?
C3 C4 C14 C12 11.4(3) . . . . ?
C11 C12 C14 C15 168.5(2) . . . . ?
C13 C12 C14 C15 -16.0(4) . . . . ?
C11 C12 C14 C4 -11.0(3) . . . . ?
C13 C12 C14 C4 164.5(2) . . . . ?
C4 C14 C15 C16 -7.2(3) . . . . ?
C12 C14 C15 C16 173.2(2) . . . . ?
C4 C14 C15 C24 174.2(2) . . . . ?
C12 C14 C15 C24 -5.4(4) . . . . ?
C14 C15 C16 C5 -6.9(3) . . . . ?
C24 C15 C16 C5 171.7(2) . . . . ?
C14 C15 C16 C23 173.6(2) . . . . ?
C24 C15 C16 C23 -7.8(3) . . . . ?
N1 C5 C16 C15 15.4(3) . . . . ?
C6 C5 C16 C15 -161.1(2) . . . . ?
N1 C5 C16 C23 -165.1(2) . . . . ?
C6 C5 C16 C23 18.4(3) . . . . ?
C6 C7 C17 C18 1.2(3) . . . . ?
C8 C7 C17 C18 -173.7(2) . . . . ?
C7 C17 C18 C19 1.2(4) . . . . ?
C17 C18 C19 C20 -2.1(4) . . . . ?
C18 C19 C20 C6 0.6(4) . . . . ?
C7 C6 C20 C19 1.8(4) . . . . ?
C5 C6 C20 C19 -173.6(2) . . . . ?
C9 C10 C21 C22 2.8(4) . . . . ?
C10 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C8 -4.5(3) . . . . ?
C21 C22 C23 C16 -179.7(2) . . . . ?
C9 C8 C23 C22 6.1(3) . . . . ?
C7 C8 C23 C22 -168.5(2) . . . . ?
C9 C8 C23 C16 -178.5(2) . . . . ?
C7 C8 C23 C16 6.8(3) . . . . ?
C15 C16 C23 C22 -26.1(3) . . . . ?
C5 C16 C23 C22 154.4(2) . . . . ?
C15 C16 C23 C8 158.8(2) . . . . ?
C5 C16 C23 C8 -20.6(3) . . . . ?
C16 C15 C24 C29 109.9(3) . . . . ?
C14 C15 C24 C29 -71.5(3) . . . . ?
C16 C15 C24 C25 -70.0(3) . . . . ?
C14 C15 C24 C25 108.6(3) . . . . ?
C29 C24 C25 C26 1.6(3) . . . . ?
C15 C24 C25 C26 -178.5(2) . . . . ?
C24 C25 C26 C27 -1.7(4) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 C29 1.0(4) . . . . ?
C25 C24 C29 C28 -0.2(3) . . . . ?
C15 C24 C29 C28 179.9(2) . . . . ?
C27 C28 C29 C24 -1.1(4) . . . . ?
