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#$Date: 2023-06-05 07:57:38 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284334 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159342.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_7159342
loop_
_publ_author_name
'Banda, Bhanu Prasad'
'Medishetti, Nagaraju'
'Nanubolu, Jagadeesh Babu'
'Atmakur, Krishnaiah'
_publ_section_title
;
 One-pot domino synthesis of five- and six-membered fused dihydropyridines
 promoted by PPh₃-NBS in aqueous medium.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4434
_journal_page_last               4439
_journal_paper_doi               10.1039/d3ob00472d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H18 F N O3'
_chemical_formula_sum            'C26 H18 F N O3'
_chemical_formula_weight         411.41
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.468(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.814(10)
_cell_length_b                   7.317(7)
_cell_length_c                   24.063(19)
_cell_measurement_reflns_used    3847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.664
_cell_measurement_theta_min      2.678
_cell_volume                     2045(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22154
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.671
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0660
_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)+(0.0625P)²+0.7823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2256
_reflns_number_total             4695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00472d2.cif
_cod_data_source_block           KB478_0m
_cod_depositor_comments          'Adding full bibliography for 7159342.cif.'
_cod_original_cell_volume        2046(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159342
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.975
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
F1 F 0.64458(19) -0.0528(4) 0.84855(8) 0.1261(10) Uani 1 1 d . . . . .
O1 O 0.40249(16) 0.3654(2) 0.54393(7) 0.0478(5) Uani 1 1 d . . . . .
O2 O 0.51520(18) -0.1574(2) 0.57762(9) 0.0647(6) Uani 1 1 d . . . . .
O3 O 0.90925(18) 0.1350(3) 0.64106(10) 0.0746(7) Uani 1 1 d . . . . .
N1 N 0.5718(2) 0.4812(3) 0.58666(10) 0.0474(6) Uani 1 1 d . . . . .
H1N H 0.540(3) 0.594(4) 0.5795(12) 0.071 Uiso 1 1 d . U . . .
C1 C 0.3278(2) 0.2209(4) 0.52815(11) 0.0454(7) Uani 1 1 d . . . . .
C2 C 0.2179(3) 0.2657(4) 0.50032(12) 0.0585(8) Uani 1 1 d . . . . .
H2 H 0.196463 0.387173 0.493729 0.070 Uiso 1 1 calc R U . . .
C3 C 0.1422(3) 0.1281(5) 0.48289(14) 0.0696(9) Uani 1 1 d . . . . .
H3 H 0.068716 0.156012 0.463598 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1733(3) -0.0532(5) 0.49352(14) 0.0711(9) Uani 1 1 d . . . . .
H4 H 0.120282 -0.145674 0.481935 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2819(3) -0.0961(4) 0.52101(12) 0.0597(8) Uani 1 1 d . . . . .
H5 H 0.302446 -0.217881 0.527720 0.072 Uiso 1 1 calc R U . . .
C6 C 0.3623(2) 0.0420(4) 0.53912(11) 0.0459(7) Uani 1 1 d . . . . .
C7 C 0.4796(2) 0.0017(3) 0.56876(11) 0.0454(7) Uani 1 1 d . . . . .
C8 C 0.5497(2) 0.1565(3) 0.58732(11) 0.0403(6) Uani 1 1 d . . . . .
C9 C 0.5086(2) 0.3279(3) 0.57356(10) 0.0405(6) Uani 1 1 d . . . . .
C10 C 0.6878(2) 0.4656(3) 0.60743(11) 0.0448(7) Uani 1 1 d . . . . .
H10 H 0.732721 0.570824 0.610862 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7391(2) 0.3049(3) 0.62298(11) 0.0433(7) Uani 1 1 d . . . . .
C12 C 0.6677(2) 0.1331(3) 0.62350(11) 0.0429(7) Uani 1 1 d . . . . .
H12 H 0.706970 0.033623 0.607390 0.052 Uiso 1 1 calc R U . . .
C13 C 0.65959(17) 0.0810(3) 0.68420(6) 0.0461(7) Uani 1 1 d G . . . .
C14 C 0.58849(17) 0.1790(3) 0.71351(9) 0.0742(10) Uani 1 1 d G . . . .
H14 H 0.544266 0.274957 0.695931 0.089 Uiso 1 1 calc R U . . .
C15 C 0.5835(2) 0.1335(4) 0.76910(9) 0.0900(12) Uani 1 1 d G . . . .
H15 H 0.535926 0.199011 0.788708 0.108 Uiso 1 1 calc R U . . .
C16 C 0.6496(2) -0.0100(4) 0.79537(7) 0.0810(12) Uani 1 1 d G . . . .
C17 C 0.7207(2) -0.1080(3) 0.76606(9) 0.0915(12) Uani 1 1 d G . . . .
H17 H 0.764918 -0.203938 0.783634 0.110 Uiso 1 1 calc R U . . .
C18 C 0.72569(17) -0.0625(3) 0.71047(9) 0.0688(9) Uani 1 1 d G . . . .
H18 H 0.773259 -0.127995 0.690858 0.083 Uiso 1 1 calc R U . . .
C19 C 0.8651(2) 0.2875(4) 0.63666(12) 0.0512(7) Uani 1 1 d . . . . .
C20 C 0.9412(2) 0.4531(4) 0.64304(12) 0.0478(7) Uani 1 1 d . . . . .
C21 C 0.9323(3) 0.5885(4) 0.68156(13) 0.0578(8) Uani 1 1 d . . . . .
H21 H 0.875706 0.580859 0.703728 0.069 Uiso 1 1 calc R U . . .
C22 C 1.0067(3) 0.7361(4) 0.68775(13) 0.0618(8) Uani 1 1 d . . . . .
H22 H 0.999892 0.825654 0.714377 0.074 Uiso 1 1 calc R U . . .
C23 C 1.0913(3) 0.7530(4) 0.65492(13) 0.0583(8) Uani 1 1 d . . . . .
C24 C 1.0999(3) 0.6161(4) 0.61671(14) 0.0640(9) Uani 1 1 d . . . . .
H24 H 1.155782 0.624428 0.594154 0.077 Uiso 1 1 calc R U . . .
C25 C 1.0273(2) 0.4664(4) 0.61109(13) 0.0591(8) Uani 1 1 d . . . . .
H25 H 1.036298 0.374031 0.585703 0.071 Uiso 1 1 calc R U . . .
C26 C 1.1692(3) 0.9175(5) 0.66127(17) 0.0887(11) Uani 1 1 d . . . . .
H26A H 1.230716 0.897778 0.640777 0.133 Uiso 1 1 calc R U . . .
H26B H 1.200693 0.936126 0.700535 0.133 Uiso 1 1 calc R U . . .
H26C H 1.126014 1.023463 0.646554 0.133 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C9 O1 C1 118.2(2) . . ?
C9 N1 C10 119.2(2) . . ?
C9 N1 H1N 121.3(19) . . ?
C10 N1 H1N 119.4(19) . . ?
C6 C1 O1 121.4(2) . . ?
C6 C1 C2 122.2(3) . . ?
O1 C1 C2 116.4(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 120.1(2) . . ?
C5 C6 C7 122.2(3) . . ?
O2 C7 C8 122.1(3) . . ?
O2 C7 C6 122.1(2) . . ?
C8 C7 C6 115.8(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 C12 119.6(2) . . ?
C7 C8 C12 120.8(2) . . ?
O1 C9 N1 111.9(2) . . ?
O1 C9 C8 124.7(2) . . ?
N1 C9 C8 123.3(3) . . ?
C11 C10 N1 122.9(2) . . ?
C11 C10 H10 118.6 . . ?
N1 C10 H10 118.6 . . ?
C10 C11 C19 121.6(2) . . ?
C10 C11 C12 120.3(2) . . ?
C19 C11 C12 118.0(2) . . ?
C8 C12 C11 110.9(2) . . ?
C8 C12 C13 111.5(2) . . ?
C11 C12 C13 110.3(2) . . ?
C8 C12 H12 108.0 . . ?
C11 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 120.32(15) . . ?
C18 C13 C12 119.67(15) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
F1 C16 C15 119.8(2) . . ?
F1 C16 C17 120.2(2) . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O3 C19 C11 119.6(3) . . ?
O3 C19 C20 119.2(3) . . ?
C11 C19 C20 121.1(2) . . ?
C21 C20 C25 118.5(3) . . ?
C21 C20 C19 122.3(3) . . ?
C25 C20 C19 119.1(3) . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 117.7(3) . . ?
C24 C23 C26 122.1(3) . . ?
C22 C23 C26 120.2(3) . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C20 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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
F1 C16 1.329(2) . ?
O1 C9 1.353(3) . ?
O1 C1 1.385(3) . ?
O2 C7 1.243(3) . ?
O3 C19 1.228(3) . ?
N1 C9 1.353(3) . ?
N1 C10 1.376(4) . ?
N1 H1N 0.91(3) . ?
C1 C6 1.382(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.469(4) . ?
C7 C8 1.427(4) . ?
C8 C9 1.364(3) . ?
C8 C12 1.513(4) . ?
C10 C11 1.345(4) . ?
C10 H10 0.9300 . ?
C11 C19 1.470(4) . ?
C11 C12 1.515(4) . ?
C12 C13 1.529(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.500(4) . ?
C20 C21 1.374(4) . ?
C20 C25 1.385(4) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(4) . ?
C23 C26 1.507(4) . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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
C9 O1 C1 C6 -3.9(3) . . . . ?
C9 O1 C1 C2 176.8(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
O1 C1 C2 C3 178.6(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
O1 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
O1 C1 C6 C7 0.8(4) . . . . ?
C2 C1 C6 C7 -180.0(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C1 C6 C7 O2 -177.3(2) . . . . ?
C5 C6 C7 O2 2.6(4) . . . . ?
C1 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C8 -176.7(2) . . . . ?
O2 C7 C8 C9 176.2(2) . . . . ?
C6 C7 C8 C9 -4.5(3) . . . . ?
O2 C7 C8 C12 -5.6(4) . . . . ?
C6 C7 C8 C12 173.7(2) . . . . ?
C1 O1 C9 N1 -179.3(2) . . . . ?
C1 O1 C9 C8 2.7(3) . . . . ?
C10 N1 C9 O1 -168.2(2) . . . . ?
C10 N1 C9 C8 9.8(4) . . . . ?
C7 C8 C9 O1 1.6(4) . . . . ?
C12 C8 C9 O1 -176.6(2) . . . . ?
C7 C8 C9 N1 -176.1(2) . . . . ?
C12 C8 C9 N1 5.7(4) . . . . ?
C9 N1 C10 C11 -9.7(4) . . . . ?
N1 C10 C11 C19 170.4(2) . . . . ?
N1 C10 C11 C12 -6.0(4) . . . . ?
C9 C8 C12 C11 -19.1(3) . . . . ?
C7 C8 C12 C11 162.7(2) . . . . ?
C9 C8 C12 C13 104.2(3) . . . . ?
C7 C8 C12 C13 -74.0(3) . . . . ?
C10 C11 C12 C8 19.3(3) . . . . ?
C19 C11 C12 C8 -157.2(2) . . . . ?
C10 C11 C12 C13 -104.7(3) . . . . ?
C19 C11 C12 C13 78.8(3) . . . . ?
C8 C12 C13 C14 -48.7(2) . . . . ?
C11 C12 C13 C14 75.0(2) . . . . ?
C8 C12 C13 C18 132.72(18) . . . . ?
C11 C12 C13 C18 -103.6(2) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C15 -178.5(2) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 F1 179.9(2) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
F1 C16 C17 C18 -179.9(2) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C12 C13 C18 C17 178.6(2) . . . . ?
C10 C11 C19 O3 -167.4(3) . . . . ?
C12 C11 C19 O3 9.1(4) . . . . ?
C10 C11 C19 C20 10.1(4) . . . . ?
C12 C11 C19 C20 -173.5(2) . . . . ?
O3 C19 C20 C21 -124.7(3) . . . . ?
C11 C19 C20 C21 57.8(4) . . . . ?
O3 C19 C20 C25 52.1(4) . . . . ?
C11 C19 C20 C25 -125.4(3) . . . . ?
C25 C20 C21 C22 0.9(4) . . . . ?
C19 C20 C21 C22 177.6(3) . . . . ?
C20 C21 C22 C23 0.8(5) . . . . ?
C21 C22 C23 C24 -1.1(4) . . . . ?
C21 C22 C23 C26 178.3(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C26 C23 C24 C25 -179.6(3) . . . . ?
C23 C24 C25 C20 1.8(5) . . . . ?
C21 C20 C25 C24 -2.1(4) . . . . ?
C19 C20 C25 C24 -179.0(3) . . . . ?
