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#$Date: 2024-05-05 04:09:16 +0300 (Sun, 05 May 2024) $
#$Revision: 291541 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132886.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_7132886
loop_
_publ_author_name
'Solanke, Pooja R.'
'Kumar, Prakash'
'Mainkar, Prathama S.'
'Nayani, Kiranmai'
'Chandrasekhar, Srivari'
_publ_section_title
;
 Synthesis of cis-fused cyclopentenone-pyrrolidine scaffolds
 via sequential aza-Piancatelli and Conia-ene type reactions in one
 pot.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4234
_journal_page_last               4237
_journal_paper_doi               10.1039/d4cc00104d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 Br N O'
_chemical_formula_sum            'C20 H16 Br N O'
_chemical_formula_weight         366.25
_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-2019/2
_audit_update_record
;
2024-01-08 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.116(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.887(2)
_cell_length_b                   13.619(3)
_cell_length_c                   11.857(2)
_cell_measurement_reflns_used    5385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      2.36
_cell_volume                     1650.8(6)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19395
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.363
_exptl_absorpt_coefficient_mu    2.494
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²+0.7599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2854
_reflns_number_total             3785
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00104d2.cif
_cod_data_source_block           bg80_m
_cod_depositor_comments
'Adding full bibliography for 7132886--7132887.cif.'
_cod_original_cell_volume        1650.7(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7132886
_shelx_shelxl_version_number     2019/2
_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   0.563
_shelx_estimated_absorpt_t_max   0.622
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
C1 C 0.7032(2) 0.35204(17) 1.1830(2) 0.0495(5) Uani 1 1 d . . . . .
C2 C 0.7783(2) 0.43212(18) 1.2347(2) 0.0495(5) Uani 1 1 d . . . . .
H2 H 0.825249 0.432361 1.316686 0.059 Uiso 1 1 calc R U . . .
C3 C 0.7845(2) 0.51216(16) 1.16542(19) 0.0461(5) Uani 1 1 d . . . . .
H3 H 0.836266 0.565705 1.201287 0.055 Uiso 1 1 calc R U . . .
C4 C 0.7140(2) 0.51387(16) 1.04182(18) 0.0408(4) Uani 1 1 d . . . . .
C5 C 0.6364(2) 0.43220(17) 0.9922(2) 0.0482(5) Uani 1 1 d . . . . .
H5 H 0.587367 0.431622 0.910596 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6313(2) 0.35201(17) 1.0626(2) 0.0532(6) Uani 1 1 d . . . . .
H6 H 0.579106 0.298272 1.028208 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6647(2) 0.59172(18) 0.84222(19) 0.0524(6) Uani 1 1 d . . . . .
H7A H 0.570875 0.581088 0.814505 0.063 Uiso 1 1 calc R U . . .
H7B H 0.705079 0.539692 0.811302 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6964(2) 0.69046(17) 0.80335(18) 0.0448(5) Uani 1 1 d . . . . .
C9 C 0.6428(3) 0.7262(2) 0.6937(2) 0.0575(6) Uani 1 1 d . . . . .
H9A H 0.581160 0.689535 0.634855 0.069 Uiso 1 1 calc R U . . .
H9B H 0.666796 0.788133 0.675320 0.069 Uiso 1 1 calc R U . . .
C10 C 0.8015(2) 0.73995(15) 0.90841(19) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.8285(2) 0.66436(15) 1.01168(18) 0.0408(4) Uani 1 1 d . . . . .
H11 H 0.832896 0.696906 1.086691 0.049 Uiso 1 1 calc R U . . .
C12 C 0.9585(2) 0.62058(18) 1.0222(2) 0.0525(6) Uani 1 1 d . . . . .
H12 H 0.996980 0.569611 1.074651 0.063 Uiso 1 1 calc R U . . .
C13 C 1.0132(2) 0.66116(18) 0.9500(2) 0.0554(6) Uani 1 1 d . . . . .
H13 H 1.093104 0.642374 0.944645 0.066 Uiso 1 1 calc R U . . .
C14 C 0.9301(2) 0.74006(16) 0.8795(2) 0.0440(5) Uani 1 1 d . . . . .
C15 C 0.7708(2) 0.84220(16) 0.94428(19) 0.0447(5) Uani 1 1 d . . . . .
C16 C 0.8690(3) 0.8931(2) 1.0309(3) 0.0677(7) Uani 1 1 d . . . . .
H16 H 0.951881 0.865356 1.062707 0.081 Uiso 1 1 calc R U . . .
C17 C 0.8462(3) 0.9841(2) 1.0707(3) 0.0821(9) Uani 1 1 d . . . . .
H17 H 0.913330 1.017330 1.128661 0.099 Uiso 1 1 calc R U . . .
C18 C 0.7244(4) 1.0254(2) 1.0248(3) 0.0814(10) Uani 1 1 d . . . . .
H18 H 0.708606 1.086698 1.051558 0.098 Uiso 1 1 calc R U . . .
C19 C 0.6263(3) 0.9766(2) 0.9396(3) 0.0744(8) Uani 1 1 d . . . . .
H19 H 0.543846 1.004983 0.908136 0.089 Uiso 1 1 calc R U . . .
C20 C 0.6487(3) 0.88459(19) 0.8996(2) 0.0569(6) Uani 1 1 d . . . . .
H20 H 0.580862 0.851520 0.842281 0.068 Uiso 1 1 calc R U . . .
N1 N 0.71857(18) 0.59513(13) 0.97310(15) 0.0457(4) Uani 1 1 d . . . . .
O1 O 0.95552(17) 0.79580(14) 0.81156(16) 0.0604(4) Uani 1 1 d . . . . .
Br1 Br 0.70102(3) 0.24142(2) 1.28011(3) 0.07559(14) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 120.2(2) . . ?
C6 C1 Br1 120.58(17) . . ?
C2 C1 Br1 119.19(18) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C4 C5 121.77(19) . . ?
N1 C4 C3 120.70(19) . . ?
C5 C4 C3 117.5(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C8 104.33(18) . . ?
N1 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 124.2(2) . . ?
C9 C8 C10 126.4(2) . . ?
C7 C8 C10 109.38(17) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C15 C10 C8 117.07(18) . . ?
C15 C10 C11 112.72(17) . . ?
C8 C10 C11 103.68(17) . . ?
C15 C10 C14 111.19(17) . . ?
C8 C10 C14 107.45(17) . . ?
C11 C10 C14 103.62(16) . . ?
N1 C11 C12 114.54(18) . . ?
N1 C11 C10 105.56(16) . . ?
C12 C11 C10 104.27(17) . . ?
N1 C11 H11 110.7 . . ?
C12 C11 H11 110.7 . . ?
C10 C11 H11 110.7 . . ?
C13 C12 C11 113.7(2) . . ?
C13 C12 H12 123.1 . . ?
C11 C12 H12 123.1 . . ?
C12 C13 C14 110.5(2) . . ?
C12 C13 H13 124.8 . . ?
C14 C13 H13 124.8 . . ?
O1 C14 C13 127.2(2) . . ?
O1 C14 C10 125.4(2) . . ?
C13 C14 C10 107.41(18) . . ?
C20 C15 C16 118.1(2) . . ?
C20 C15 C10 123.4(2) . . ?
C16 C15 C10 118.4(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.4(3) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C4 N1 C7 121.17(18) . . ?
C4 N1 C11 121.36(17) . . ?
C7 N1 C11 109.79(17) . . ?
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
C1 C6 1.371(3) . ?
C1 C2 1.375(3) . ?
C1 Br1 1.901(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.385(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.459(3) . ?
C7 C8 1.500(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.322(3) . ?
C8 C10 1.528(3) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C15 1.526(3) . ?
C10 C11 1.548(3) . ?
C10 C14 1.552(3) . ?
C11 N1 1.467(3) . ?
C11 C12 1.501(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.320(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.467(3) . ?
C13 H13 0.9300 . ?
C14 O1 1.206(3) . ?
C15 C20 1.377(3) . ?
C15 C16 1.387(4) . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
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
C6 C1 C2 C3 -1.5(4) . . . . ?
Br1 C1 C2 C3 178.12(17) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 N1 178.8(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
N1 C4 C5 C6 -179.0(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
Br1 C1 C6 C5 -178.34(17) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
N1 C7 C8 C9 -165.5(2) . . . . ?
N1 C7 C8 C10 16.2(2) . . . . ?
C9 C8 C10 C15 56.4(3) . . . . ?
C7 C8 C10 C15 -125.3(2) . . . . ?
C9 C8 C10 C11 -178.8(2) . . . . ?
C7 C8 C10 C11 -0.5(2) . . . . ?
C9 C8 C10 C14 -69.5(3) . . . . ?
C7 C8 C10 C14 108.8(2) . . . . ?
C15 C10 C11 N1 112.23(19) . . . . ?
C8 C10 C11 N1 -15.3(2) . . . . ?
C14 C10 C11 N1 -127.46(17) . . . . ?
C15 C10 C11 C12 -126.7(2) . . . . ?
C8 C10 C11 C12 105.69(19) . . . . ?
C14 C10 C11 C12 -6.4(2) . . . . ?
N1 C11 C12 C13 118.8(2) . . . . ?
C10 C11 C12 C13 3.9(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 O1 174.6(2) . . . . ?
C12 C13 C14 C10 -5.0(3) . . . . ?
C15 C10 C14 O1 -51.3(3) . . . . ?
C8 C10 C14 O1 78.0(3) . . . . ?
C11 C10 C14 O1 -172.6(2) . . . . ?
C15 C10 C14 C13 128.4(2) . . . . ?
C8 C10 C14 C13 -102.3(2) . . . . ?
C11 C10 C14 C13 7.0(2) . . . . ?
C8 C10 C15 C20 9.9(3) . . . . ?
C11 C10 C15 C20 -110.2(2) . . . . ?
C14 C10 C15 C20 133.9(2) . . . . ?
C8 C10 C15 C16 -173.5(2) . . . . ?
C11 C10 C15 C16 66.4(3) . . . . ?
C14 C10 C15 C16 -49.5(3) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?
C10 C15 C16 C17 -177.4(3) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C10 C15 C20 C19 177.5(2) . . . . ?
C18 C19 C20 C15 -0.9(4) . . . . ?
C5 C4 N1 C7 -12.8(3) . . . . ?
C3 C4 N1 C7 169.3(2) . . . . ?
C5 C4 N1 C11 -159.1(2) . . . . ?
C3 C4 N1 C11 23.0(3) . . . . ?
C8 C7 N1 C4 -176.64(19) . . . . ?
C8 C7 N1 C11 -26.9(2) . . . . ?
C12 C11 N1 C4 62.5(3) . . . . ?
C10 C11 N1 C4 176.63(18) . . . . ?
C12 C11 N1 C7 -87.2(2) . . . . ?
C10 C11 N1 C7 26.9(2) . . . . ?
