#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:22 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273423 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158489.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_7158489
loop_
_publ_author_name
'Rajput, Shruti'
'Kaur, Ramandeep'
'Jain, Nidhi'
_publ_section_title
;
 Pd and photoredox dual catalysis assisted decarboxylative
 ortho-benzoylation of N-phenyl-7-azaindoles.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1453
_journal_page_last               1461
_journal_paper_doi               10.1039/d1ob02338a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H13 Br N2 O'
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-18 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                99.581(2)
_cell_angle_beta                 107.210(2)
_cell_angle_gamma                100.420(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0295(5)
_cell_length_b                   8.2401(7)
_cell_length_c                   13.3944(10)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.58
_cell_volume                     809.44(11)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.1459
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10899
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.637
_exptl_absorpt_coefficient_mu    2.542
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      1.544
_exptl_crystal_description       block
_exptl_crystal_F_000             380.0
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.306
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.105(10)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0545
_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)+(0.0689P)²+3.2013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2490
_reflns_number_total             2854
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02338a2.cif
_cod_data_source_block           st306_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158489.cif.
;
_cod_original_cell_volume        809.45(11)
_cod_database_code               7158489
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.28411(6) 0.74555(5) 0.32838(3) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.6579(6) 1.0553(5) 0.8550(4) 0.0397(10) Uani 1 1 d . . . . .
N1 N 0.4433(7) 0.5416(6) 0.7548(4) 0.0335(11) Uani 1 1 d . . . . .
N2 N 0.5377(7) 0.7255(6) 0.6507(4) 0.0362(12) Uani 1 1 d . . . . .
C8 C 0.5837(8) 0.6097(8) 0.8547(5) 0.0334(13) Uani 1 1 d . . . . .
C2 C 0.3364(8) 0.6684(8) 0.4691(5) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.6631(9) 0.5006(8) 0.9098(5) 0.0378(14) Uani 1 1 d . . . . .
H9 H 0.618539 0.381489 0.882018 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2668(8) 0.4937(7) 0.5809(5) 0.0346(13) Uani 1 1 d . . . . .
C13 C 0.6468(8) 0.7876(8) 0.8969(5) 0.0350(13) Uani 1 1 d . . . . .
C10 C 0.8070(9) 0.5630(9) 1.0051(5) 0.0416(15) Uani 1 1 d . . . . .
H10 H 0.858082 0.486784 1.043433 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2209(8) 0.5317(8) 0.4810(5) 0.0342(13) Uani 1 1 d . . . . .
H3 H 0.115820 0.467577 0.423518 0.041 Uiso 1 1 calc R U . . .
C17 C 0.0695(9) 0.7620(8) 0.8140(5) 0.0369(14) Uani 1 1 d . . . . .
H17 H -0.003694 0.690797 0.841570 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4916(9) 0.7589(8) 0.5532(5) 0.0369(14) Uani 1 1 d . . . . .
H1 H 0.568948 0.849237 0.540721 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4235(8) 0.5965(7) 0.6612(5) 0.0324(13) Uani 1 1 d . . . . .
C16 C 0.2554(8) 0.7816(7) 0.8498(5) 0.0342(13) Uani 1 1 d . . . . .
H16 H 0.308309 0.722622 0.901188 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3016(9) 0.4023(7) 0.7331(5) 0.0387(14) Uani 1 1 d . . . . .
H6 H 0.283268 0.338766 0.783663 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3646(8) 0.8882(7) 0.8102(5) 0.0328(13) Uani 1 1 d . . . . .
C12 C 0.7964(8) 0.8468(8) 0.9899(5) 0.0367(14) Uani 1 1 d . . . . .
H12 H 0.844850 0.965658 1.016587 0.044 Uiso 1 1 calc R U . . .
C14 C 0.5623(8) 0.9183(7) 0.8508(5) 0.0336(13) Uani 1 1 d . . . . .
C11 C 0.8766(9) 0.7376(9) 1.0446(5) 0.0418(15) Uani 1 1 d . . . . .
H11 H 0.978033 0.781070 1.108442 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0085(9) 0.8461(8) 0.7383(5) 0.0394(15) Uani 1 1 d . . . . .
H18 H -0.135081 0.832744 0.713755 0.047 Uiso 1 1 calc R U . . .
C19 C 0.0999(9) 0.9506(8) 0.6981(6) 0.0417(15) Uani 1 1 d . . . . .
H19 H 0.046385 1.007262 0.645463 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1931(9) 0.3697(8) 0.6296(5) 0.0388(14) Uani 1 1 d . . . . .
H5 H 0.087197 0.280700 0.595388 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2852(8) 0.9727(7) 0.7344(5) 0.0371(14) Uani 1 1 d . . . . .
H20 H 0.357897 1.045592 0.707391 0.044 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'
Br Br -0.2901 2.4595 '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'
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
C7 N1 C6 107.3(5) . . ?
C7 N1 C8 127.3(5) . . ?
C6 N1 C8 125.4(5) . . ?
C7 N2 C1 114.5(5) . . ?
C9 C8 N1 119.1(5) . . ?
C9 C8 C13 119.9(6) . . ?
N1 C8 C13 120.9(5) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 Br1 121.4(5) . . ?
C1 C2 Br1 117.5(5) . . ?
C8 C9 C10 120.7(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C3 C4 C7 117.8(6) . . ?
C3 C4 C5 136.3(6) . . ?
C7 C4 C5 105.9(5) . . ?
C12 C13 C8 118.0(6) . . ?
C12 C13 C14 116.8(5) . . ?
C8 C13 C14 125.2(5) . . ?
C9 C10 C11 120.0(6) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C4 C3 C2 116.4(5) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
C18 C17 C16 120.2(6) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N2 C1 C2 123.4(6) . . ?
N2 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
N2 C7 N1 124.3(5) . . ?
N2 C7 C4 126.6(6) . . ?
N1 C7 C4 109.1(5) . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C5 C6 N1 110.2(6) . . ?
C5 C6 H6 124.9 . . ?
N1 C6 H6 124.9 . . ?
C20 C15 C16 119.3(6) . . ?
C20 C15 C14 119.3(5) . . ?
C16 C15 C14 121.4(5) . . ?
C11 C12 C13 121.9(6) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O1 C14 C15 120.4(5) . . ?
O1 C14 C13 119.6(6) . . ?
C15 C14 C13 119.8(5) . . ?
C12 C11 C10 119.2(6) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.7(6) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C6 C5 C4 107.6(6) . . ?
C6 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
C19 C20 C15 120.1(6) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
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 C2 2.040(6) . ?
O1 C14 1.227(7) . ?
N1 C7 1.378(8) . ?
N1 C6 1.385(8) . ?
N1 C8 1.416(8) . ?
N2 C7 1.328(8) . ?
N2 C1 1.338(8) . ?
C8 C9 1.381(8) . ?
C8 C13 1.418(9) . ?
C2 C3 1.386(9) . ?
C2 C1 1.389(9) . ?
C9 C10 1.387(9) . ?
C9 H9 0.9500 . ?
C4 C3 1.384(9) . ?
C4 C7 1.402(8) . ?
C4 C5 1.432(9) . ?
C13 C12 1.390(9) . ?
C13 C14 1.496(8) . ?
C10 C11 1.394(10) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C17 C18 1.384(9) . ?
C17 C16 1.396(9) . ?
C17 H17 0.9500 . ?
C1 H1 0.9500 . ?
C16 C15 1.405(8) . ?
C16 H16 0.9500 . ?
C6 C5 1.353(9) . ?
C6 H6 0.9500 . ?
C15 C20 1.391(8) . ?
C15 C14 1.476(8) . ?
C12 C11 1.383(9) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C18 C19 1.396(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(9) . ?
C19 H19 0.9500 . ?
C5 H5 0.9500 . ?
C20 H20 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
C7 N1 C8 C9 -134.2(6) . . . . ?
C6 N1 C8 C9 44.0(9) . . . . ?
C7 N1 C8 C13 43.9(9) . . . . ?
C6 N1 C8 C13 -137.9(6) . . . . ?
N1 C8 C9 C10 176.7(6) . . . . ?
C13 C8 C9 C10 -1.4(10) . . . . ?
C9 C8 C13 C12 4.3(9) . . . . ?
N1 C8 C13 C12 -173.8(6) . . . . ?
C9 C8 C13 C14 -174.0(6) . . . . ?
N1 C8 C13 C14 7.9(9) . . . . ?
C8 C9 C10 C11 -2.0(10) . . . . ?
C7 C4 C3 C2 0.6(9) . . . . ?
C5 C4 C3 C2 -179.8(7) . . . . ?
C1 C2 C3 C4 1.3(9) . . . . ?
Br1 C2 C3 C4 -178.1(4) . . . . ?
C7 N2 C1 C2 0.6(9) . . . . ?
C3 C2 C1 N2 -2.1(10) . . . . ?
Br1 C2 C1 N2 177.3(5) . . . . ?
C1 N2 C7 N1 -179.2(6) . . . . ?
C1 N2 C7 C4 1.6(9) . . . . ?
C6 N1 C7 N2 -178.2(6) . . . . ?
C8 N1 C7 N2 0.3(10) . . . . ?
C6 N1 C7 C4 1.2(7) . . . . ?
C8 N1 C7 C4 179.7(6) . . . . ?
C3 C4 C7 N2 -2.2(10) . . . . ?
C5 C4 C7 N2 178.1(6) . . . . ?
C3 C4 C7 N1 178.4(5) . . . . ?
C5 C4 C7 N1 -1.3(7) . . . . ?
C18 C17 C16 C15 0.7(9) . . . . ?
C7 N1 C6 C5 -0.7(7) . . . . ?
C8 N1 C6 C5 -179.2(6) . . . . ?
C17 C16 C15 C20 -0.5(9) . . . . ?
C17 C16 C15 C14 176.8(6) . . . . ?
C8 C13 C12 C11 -3.9(10) . . . . ?
C14 C13 C12 C11 174.5(6) . . . . ?
C20 C15 C14 O1 29.3(9) . . . . ?
C16 C15 C14 O1 -148.1(6) . . . . ?
C20 C15 C14 C13 -156.6(6) . . . . ?
C16 C15 C14 C13 26.1(8) . . . . ?
C12 C13 C14 O1 36.4(9) . . . . ?
C8 C13 C14 O1 -145.3(6) . . . . ?
C12 C13 C14 C15 -137.8(6) . . . . ?
C8 C13 C14 C15 40.5(9) . . . . ?
C13 C12 C11 C10 0.6(10) . . . . ?
C9 C10 C11 C12 2.4(10) . . . . ?
C16 C17 C18 C19 -0.1(10) . . . . ?
C17 C18 C19 C20 -0.8(10) . . . . ?
N1 C6 C5 C4 -0.1(8) . . . . ?
C3 C4 C5 C6 -178.7(7) . . . . ?
C7 C4 C5 C6 0.9(7) . . . . ?
C18 C19 C20 C15 1.0(10) . . . . ?
C16 C15 C20 C19 -0.3(9) . . . . ?
C14 C15 C20 C19 -177.7(6) . . . . ?
