#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128020.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_7128020
loop_
_publ_author_name
'Ramesh, Balu'
'Jeganmohan, Masilamani'
_publ_section_title
;
 Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of
 N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room
 temperature.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3692
_journal_page_last               3695
_journal_paper_doi               10.1039/d1cc00654a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23
_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-2014/7
_audit_update_record
;
2020-10-28 deposited with the CCDC.	2021-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.258(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4966(16)
_cell_length_b                   10.4123(11)
_cell_length_c                   11.2334(10)
_cell_measurement_reflns_used    1390
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.84
_cell_measurement_theta_min      2.76
_cell_volume                     1580.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9144
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.507
_exptl_absorpt_coefficient_mu    2.599
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.674
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.674
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0576
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1552
_reflns_number_total             2783
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00654a2.cif
_cod_data_source_block           62
_cod_depositor_comments          'Adding full bibliography for 7128020.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128020
_shelx_shelxl_version_number     2014/7
_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   0.781
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
Br1 Br 0.48841(5) 0.63607(6) 1.26431(5) 0.0793(3) Uani 1 1 d . . . . .
C1 C 0.2700(4) 0.9142(5) 1.1496(4) 0.0471(15) Uani 1 1 d . . . . .
H1 H 0.2212 0.9442 1.1781 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3326(4) 0.8154(5) 1.2153(4) 0.0521(17) Uani 1 1 d . . . . .
H2 H 0.3255 0.7799 1.2875 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4040(4) 0.7707(5) 1.1743(4) 0.0412(14) Uani 1 1 d . . . . .
C4 C 0.4153(4) 0.8223(5) 1.0685(4) 0.0443(15) Uani 1 1 d . . . . .
H4 H 0.4646 0.7918 1.0412 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3528(4) 0.9204(4) 1.0019(4) 0.0373(14) Uani 1 1 d . . . . .
H5 H 0.3605 0.9542 0.9293 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2802(4) 0.9687(4) 1.0406(4) 0.0285(13) Uani 1 1 d . . . . .
C7 C 0.2112(4) 1.0768(4) 0.9718(4) 0.0328(13) Uani 1 1 d . . . . .
H7 H 0.2293 1.1524 1.0275 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2189(3) 1.1145(4) 0.8459(4) 0.0307(13) Uani 1 1 d . . . . .
C9 C 0.3061(4) 1.1935(5) 0.8494(4) 0.0476(15) Uani 1 1 d . . . . .
H9A H 0.3545 1.2154 0.9325 0.057 Uiso 1 1 calc R U . . .
H9B H 0.3334 1.1784 0.7835 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2074(4) 1.2551(5) 0.8109(5) 0.0537(16) Uani 1 1 d . . . . .
H10A H 0.1745 1.2772 0.7215 0.064 Uiso 1 1 calc R U . . .
H10B H 0.1957 1.3142 0.8706 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1714(4) 1.0202(5) 0.7435(4) 0.0324(13) Uani 1 1 d . . . . .
C12 C 0.2014(4) 0.9980(5) 0.6402(4) 0.0416(15) Uani 1 1 d . . . . .
H12 H 0.2556 1.0424 0.6354 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1520(5) 0.9113(5) 0.5446(5) 0.0461(16) Uani 1 1 d . . . . .
C14 C 0.0730(4) 0.8438(5) 0.5538(4) 0.0508(16) Uani 1 1 d . . . . .
H14 H 0.0406 0.7835 0.4915 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0415(4) 0.8645(5) 0.6543(4) 0.0455(14) Uani 1 1 d . . . . .
H15 H -0.0123 0.8189 0.6589 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0898(4) 0.9535(5) 0.7489(4) 0.0317(13) Uani 1 1 d . . . . .
C17 C 0.0503(4) 0.9766(5) 0.8523(4) 0.0335(14) Uani 1 1 d . . . . .
C18 C 0.1847(4) 0.8882(5) 0.4326(4) 0.0655(18) Uani 1 1 d . . . . .
H18A H 0.1861 0.7976 0.4176 0.098 Uiso 1 1 calc R U . . .
H18B H 0.2497 0.9235 0.4514 0.098 Uiso 1 1 calc R U . . .
H18C H 0.1391 0.9290 0.3577 0.098 Uiso 1 1 calc R U . . .
N1 N 0.1083(3) 1.0470(4) 0.9509(4) 0.0352(12) Uani 1 1 d . . . . .
O1 O -0.0315(3) 0.9378(3) 0.8458(3) 0.0476(10) Uani 1 1 d . . . . .
H1N H 0.088(3) 1.054(4) 1.008(3) 0.013(14) Uiso 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
C2 C1 C6 120.4(5) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 Br1 119.8(4) . . ?
C4 C3 Br1 119.8(4) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 117.6(4) . . ?
C5 C6 C7 123.3(4) . . ?
C1 C6 C7 119.1(5) . . ?
N1 C7 C8 108.9(4) . . ?
N1 C7 C6 111.7(4) . . ?
C8 C7 C6 114.3(4) . . ?
N1 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
C11 C8 C9 122.5(4) . . ?
C11 C8 C10 117.7(4) . . ?
C9 C8 C10 59.1(3) . . ?
C11 C8 C7 112.6(4) . . ?
C9 C8 C7 117.8(4) . . ?
C10 C8 C7 117.2(4) . . ?
C10 C9 C8 60.9(3) . . ?
C10 C9 H9A 117.7 . . ?
C8 C9 H9A 117.7 . . ?
C10 C9 H9B 117.7 . . ?
C8 C9 H9B 117.7 . . ?
H9A C9 H9B 114.8 . . ?
C9 C10 C8 60.0(3) . . ?
C9 C10 H10A 117.8 . . ?
C8 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C8 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
C16 C11 C12 118.6(5) . . ?
C16 C11 C8 117.5(4) . . ?
C12 C11 C8 123.9(5) . . ?
C13 C12 C11 121.4(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 C18 119.9(5) . . ?
C12 C13 C18 121.1(6) . . ?
C13 C14 C15 120.7(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 C17 118.3(5) . . ?
C11 C16 C17 121.7(4) . . ?
O1 C17 N1 122.1(5) . . ?
O1 C17 C16 122.4(5) . . ?
N1 C17 C16 115.5(5) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N1 C7 123.3(5) . . ?
C17 N1 H1N 114(3) . . ?
C7 N1 H1N 120(3) . . ?
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
Br1 C3 1.894(5) . ?
C1 C2 1.394(6) . ?
C1 C6 1.405(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(6) . ?
C4 C5 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(6) . ?
C7 N1 1.457(6) . ?
C7 C8 1.511(6) . ?
C7 H7 0.9800 . ?
C8 C11 1.478(6) . ?
C8 C9 1.496(6) . ?
C8 C10 1.510(6) . ?
C9 C10 1.482(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.393(6) . ?
C11 C12 1.398(6) . ?
C12 C13 1.386(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(7) . ?
C13 C18 1.517(6) . ?
C14 C15 1.381(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(6) . ?
C17 O1 1.231(5) . ?
C17 N1 1.340(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1N 0.80(4) . ?
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 -0.1(8) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C1 C2 C3 Br1 -179.9(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
Br1 C3 C4 C5 179.5(4) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C4 C5 C6 C7 179.2(4) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C6 C7 -179.6(4) . . . . ?
C5 C6 C7 N1 132.7(5) . . . . ?
C1 C6 C7 N1 -47.3(6) . . . . ?
C5 C6 C7 C8 8.5(7) . . . . ?
C1 C6 C7 C8 -171.5(4) . . . . ?
N1 C7 C8 C11 -50.8(5) . . . . ?
C6 C7 C8 C11 74.9(5) . . . . ?
N1 C7 C8 C9 158.0(4) . . . . ?
C6 C7 C8 C9 -76.3(5) . . . . ?
N1 C7 C8 C10 90.5(5) . . . . ?
C6 C7 C8 C10 -143.8(4) . . . . ?
C11 C8 C9 C10 105.2(5) . . . . ?
C7 C8 C9 C10 -106.6(5) . . . . ?
C11 C8 C10 C9 -113.1(5) . . . . ?
C7 C8 C10 C9 107.7(5) . . . . ?
C9 C8 C11 C16 -179.0(4) . . . . ?
C10 C8 C11 C16 -109.8(5) . . . . ?
C7 C8 C11 C16 31.3(6) . . . . ?
C9 C8 C11 C12 -1.4(7) . . . . ?
C10 C8 C11 C12 67.8(6) . . . . ?
C7 C8 C11 C12 -151.1(4) . . . . ?
C16 C11 C12 C13 -0.3(7) . . . . ?
C8 C11 C12 C13 -177.9(4) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C11 C12 C13 C18 179.7(4) . . . . ?
C12 C13 C14 C15 1.9(8) . . . . ?
C18 C13 C14 C15 -179.3(4) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C14 C15 C16 C11 -1.2(7) . . . . ?
C14 C15 C16 C17 177.4(4) . . . . ?
C12 C11 C16 C15 1.6(7) . . . . ?
C8 C11 C16 C15 179.3(4) . . . . ?
C12 C11 C16 C17 -176.9(4) . . . . ?
C8 C11 C16 C17 0.8(7) . . . . ?
C15 C16 C17 O1 -12.7(7) . . . . ?
C11 C16 C17 O1 165.8(5) . . . . ?
C15 C16 C17 N1 169.7(4) . . . . ?
C11 C16 C17 N1 -11.8(7) . . . . ?
O1 C17 N1 C7 169.8(5) . . . . ?
C16 C17 N1 C7 -12.6(7) . . . . ?
C8 C7 N1 C17 43.6(6) . . . . ?
C6 C7 N1 C17 -83.5(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352600
