#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:44:38 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159158.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_7159158
loop_
_publ_author_name
'Dhillon, Prakriti'
'Anaspure, Prasad'
'Wiklander, Jesper G.'
'Kathiravan, Subban'
'Nicholls, Ian A.'
_publ_section_title
;
 Diyne-steered switchable regioselectivity in cobalt(II)-catalysed
 C(sp²)-H activation of amides with unsymmetrical 1,3-diynes.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1942
_journal_page_last               1951
_journal_paper_doi               10.1039/d2ob02193e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C28 H19 Br N2 O2'
_chemical_formula_weight         495.36
_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
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0039(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3549(3)
_cell_length_b                   10.5712(4)
_cell_length_c                   18.7259(6)
_cell_measurement_reflns_used    9060
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.63
_cell_volume                     2244.67(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.796
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0350
_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)+(0.0378P)²+1.8119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3207
_reflns_number_total             3966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02193e2.cif
_cod_data_source_block           ch3
_cod_depositor_comments
'Adding full bibliography for 7159156--7159161.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159158
_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   0.605
_shelx_estimated_absorpt_t_max   0.755
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 0.64279(3) 1.48638(3) 0.16204(2) 0.05775(13) Uani 1 1 d . . . . .
C1 C 0.3965(2) 1.2122(2) 0.10443(12) 0.0348(5) Uani 1 1 d . . . . .
C2 C 0.4617(2) 1.3054(2) 0.14127(13) 0.0403(6) Uani 1 1 d . . . . .
H2 H 0.4442 1.3268 0.1877 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5512(2) 1.3649(2) 0.10904(14) 0.0426(6) Uani 1 1 d . . . . .
C4 C 0.5785(2) 1.3348(3) 0.03949(15) 0.0486(7) Uani 1 1 d . . . . .
H4 H 0.6399 1.3759 0.0181 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5140(2) 1.2442(3) 0.00283(13) 0.0443(6) Uani 1 1 d . . . . .
H5 H 0.5322 1.2246 -0.0437 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4210(2) 1.1801(2) 0.03392(12) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.3521(2) 1.0836(2) -0.00323(12) 0.0340(5) Uani 1 1 d . . . . .
C8 C 0.2707(2) 1.0201(2) 0.03296(12) 0.0331(5) Uani 1 1 d . . . . .
C9 C 0.3063(2) 1.1445(2) 0.14246(12) 0.0354(6) Uani 1 1 d . . . . .
C10 C 0.3645(2) 1.0598(2) -0.08205(12) 0.0364(6) Uani 1 1 d . . . . .
H10A H 0.3314 0.9778 -0.0948 0.044 Uiso 1 1 calc R U . . .
H10B H 0.4474 1.0591 -0.0923 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3013(2) 1.1616(2) -0.12612(12) 0.0377(6) Uani 1 1 d . . . . .
H11A H 0.2196 1.1668 -0.1137 0.045 Uiso 1 1 calc R U . . .
H11B H 0.3383 1.2430 -0.1164 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1968(2) 0.9225(2) 0.00285(12) 0.0373(6) Uani 1 1 d . . . . .
C13 C 0.1320(2) 0.8397(2) -0.01783(13) 0.0410(6) Uani 1 1 d . . . . .
C14 C 0.0489(2) 0.7426(2) -0.03827(13) 0.0406(6) Uani 1 1 d . . . . .
C15 C 0.0661(3) 0.6635(3) -0.09513(15) 0.0620(9) Uani 1 1 d . . . . .
H15 H 0.1329 0.6721 -0.1214 0.074 Uiso 1 1 calc R U . . .
C16 C -0.0165(4) 0.5710(4) -0.11303(18) 0.0840(12) Uani 1 1 d . . . . .
H16 H -0.0046 0.5171 -0.1513 0.101 Uiso 1 1 calc R U . . .
C17 C -0.1154(4) 0.5580(4) -0.0751(2) 0.0777(11) Uani 1 1 d . . . . .
H17 H -0.1709 0.4962 -0.0878 0.093 Uiso 1 1 calc R U . . .
C18 C -0.1327(3) 0.6357(4) -0.0186(2) 0.0764(10) Uani 1 1 d . . . . .
H18 H -0.1996 0.6266 0.0075 0.092 Uiso 1 1 calc R U . . .
C19 C -0.0511(3) 0.7275(3) -0.00031(18) 0.0624(8) Uani 1 1 d . . . . .
H19 H -0.0634 0.7803 0.0383 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1791(2) 0.9623(2) 0.14425(12) 0.0327(5) Uani 1 1 d . . . . .
C21 C 0.2341(2) 0.8515(2) 0.17151(12) 0.0326(5) Uani 1 1 d . . . . .
C22 C 0.3995(3) 0.7309(3) 0.18933(15) 0.0531(7) Uani 1 1 d . . . . .
H22 H 0.4793 0.7181 0.1829 0.064 Uiso 1 1 calc R U . . .
C23 C 0.3416(3) 0.6408(3) 0.22840(16) 0.0587(8) Uani 1 1 d . . . . .
H23 H 0.3816 0.5707 0.2473 0.070 Uiso 1 1 calc R U . . .
C24 C 0.2255(3) 0.6574(3) 0.23823(15) 0.0549(8) Uani 1 1 d . . . . .
H24 H 0.1845 0.5978 0.2638 0.066 Uiso 1 1 calc R U . . .
C25 C 0.1663(2) 0.7650(2) 0.20983(13) 0.0398(6) Uani 1 1 d . . . . .
C26 C 0.0465(2) 0.7912(3) 0.21818(14) 0.0486(7) Uani 1 1 d . . . . .
H26 H 0.0006 0.7338 0.2421 0.058 Uiso 1 1 calc R U . . .
C27 C -0.0029(2) 0.8989(3) 0.19189(15) 0.0509(7) Uani 1 1 d . . . . .
H27 H -0.0820 0.9155 0.1987 0.061 Uiso 1 1 calc R U . . .
C28 C 0.0640(2) 0.9864(3) 0.15429(14) 0.0436(6) Uani 1 1 d . . . . .
H28 H 0.0292 1.0604 0.1364 0.052 Uiso 1 1 calc R U . . .
N1 N 0.25032(18) 1.04847(18) 0.10498(9) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.35090(18) 0.8324(2) 0.16075(11) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.28208(18) 1.16649(17) 0.20467(9) 0.0494(5) Uani 1 1 d . . . . .
O2 O 0.30722(18) 1.13139(19) -0.19944(9) 0.0457(5) Uani 1 1 d . . . . .
H1O H 0.291(3) 1.191(3) -0.2225(17) 0.065(11) 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 120.6(2) . . ?
C2 C1 C9 118.2(2) . . ?
C6 C1 C9 121.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 Br1 118.78(19) . . ?
C4 C3 Br1 120.1(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 122.8(2) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 C10 120.5(2) . . ?
C6 C7 C10 120.9(2) . . ?
C7 C8 N1 121.6(2) . . ?
C7 C8 C12 124.3(2) . . ?
N1 C8 C12 114.1(2) . . ?
O1 C9 N1 120.2(2) . . ?
O1 C9 C1 124.3(2) . . ?
N1 C9 C1 115.48(19) . . ?
C7 C10 C11 110.4(2) . . ?
C7 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C7 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C10 108.9(2) . . ?
O2 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C8 175.5(3) . . ?
C12 C13 C14 175.7(3) . . ?
C15 C14 C19 118.8(3) . . ?
C15 C14 C13 121.6(3) . . ?
C19 C14 C13 119.6(2) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 121.1(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C28 C20 C21 121.2(2) . . ?
C28 C20 N1 121.5(2) . . ?
C21 C20 N1 117.3(2) . . ?
N2 C21 C20 118.9(2) . . ?
N2 C21 C25 122.5(2) . . ?
C20 C21 C25 118.6(2) . . ?
N2 C22 C23 125.3(3) . . ?
N2 C22 H22 117.3 . . ?
C23 C22 H22 117.3 . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 124.2(2) . . ?
C26 C25 C21 119.0(2) . . ?
C24 C25 C21 116.8(2) . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C20 C28 C27 119.7(3) . . ?
C20 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C9 N1 C8 123.4(2) . . ?
C9 N1 C20 117.59(18) . . ?
C8 N1 C20 118.45(19) . . ?
C22 N2 C21 116.9(2) . . ?
C11 O2 H1O 109(2) . . ?
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 1.899(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.405(3) . ?
C1 C9 1.464(3) . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(3) . ?
C7 C8 1.353(3) . ?
C7 C10 1.511(3) . ?
C8 N1 1.413(3) . ?
C8 C12 1.427(4) . ?
C9 O1 1.233(3) . ?
C9 N1 1.371(3) . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.415(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.194(4) . ?
C13 C14 1.433(4) . ?
C14 C15 1.376(4) . ?
C14 C19 1.380(4) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C28 1.355(4) . ?
C20 C21 1.411(3) . ?
C20 N1 1.444(3) . ?
C21 N2 1.367(3) . ?
C21 C25 1.415(3) . ?
C22 N2 1.308(3) . ?
C22 C23 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.352(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.411(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.406(4) . ?
C26 C27 1.350(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.409(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O2 H1O 0.78(3) . ?
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 -0.9(4) . . . . ?
C9 C1 C2 C3 176.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 Br1 -177.38(18) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Br1 C3 C4 C5 177.9(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C9 C1 C6 C5 -176.0(2) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C9 C1 C6 C7 3.4(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C1 C6 C7 C8 -4.6(3) . . . . ?
C5 C6 C7 C8 174.8(2) . . . . ?
C1 C6 C7 C10 171.3(2) . . . . ?
C5 C6 C7 C10 -9.3(4) . . . . ?
C6 C7 C8 N1 1.6(3) . . . . ?
C10 C7 C8 N1 -174.3(2) . . . . ?
C6 C7 C8 C12 -179.9(2) . . . . ?
C10 C7 C8 C12 4.2(4) . . . . ?
C2 C1 C9 O1 1.9(4) . . . . ?
C6 C1 C9 O1 178.7(2) . . . . ?
C2 C1 C9 N1 -176.0(2) . . . . ?
C6 C1 C9 N1 0.8(3) . . . . ?
C8 C7 C10 C11 99.4(3) . . . . ?
C6 C7 C10 C11 -76.4(3) . . . . ?
C7 C10 C11 O2 -175.7(2) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C13 C14 C15 C16 -179.9(3) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C14 -0.1(6) . . . . ?
C15 C14 C19 C18 -0.2(5) . . . . ?
C13 C14 C19 C18 179.8(3) . . . . ?
C28 C20 C21 N2 -179.1(2) . . . . ?
N1 C20 C21 N2 1.2(3) . . . . ?
C28 C20 C21 C25 0.1(3) . . . . ?
N1 C20 C21 C25 -179.6(2) . . . . ?
N2 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C26 -179.0(3) . . . . ?
C23 C24 C25 C21 0.1(4) . . . . ?
N2 C21 C25 C26 -179.6(2) . . . . ?
C20 C21 C25 C26 1.2(3) . . . . ?
N2 C21 C25 C24 1.2(4) . . . . ?
C20 C21 C25 C24 -178.0(2) . . . . ?
C24 C25 C26 C27 177.3(3) . . . . ?
C21 C25 C26 C27 -1.8(4) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C21 C20 C28 C27 -0.7(4) . . . . ?
N1 C20 C28 C27 178.9(2) . . . . ?
C26 C27 C28 C20 0.1(4) . . . . ?
O1 C9 N1 C8 178.0(2) . . . . ?
C1 C9 N1 C8 -4.1(3) . . . . ?
O1 C9 N1 C20 -10.5(3) . . . . ?
C1 C9 N1 C20 167.4(2) . . . . ?
C7 C8 N1 C9 2.9(4) . . . . ?
C12 C8 N1 C9 -175.7(2) . . . . ?
C7 C8 N1 C20 -168.5(2) . . . . ?
C12 C8 N1 C20 12.9(3) . . . . ?
C28 C20 N1 C9 88.0(3) . . . . ?
C21 C20 N1 C9 -92.4(3) . . . . ?
C28 C20 N1 C8 -100.1(3) . . . . ?
C21 C20 N1 C8 79.6(3) . . . . ?
C23 C22 N2 C21 1.1(4) . . . . ?
C20 C21 N2 C22 177.4(2) . . . . ?
C25 C21 N2 C22 -1.8(4) . . . . ?
