#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:38:58 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281557 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159103.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_7159103
loop_
_publ_author_name
'Sankaram, G. Siva'
'Sahoo, Tanmoy'
'Sridhar, B.'
'Subba Reddy, B. V.'
_publ_section_title
;
 Rhodium(III)-catalyzed oxidative annulation of N-arylbenzamidines
 with maleimides via dual C-H activation.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1719
_journal_page_last               1724
_journal_paper_doi               10.1039/d2ob01972h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H15 N3 O2'
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_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-2018/3
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.911(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6673(18)
_cell_length_b                   10.263(2)
_cell_length_c                   20.044(4)
_cell_measurement_reflns_used    9359
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      3.3305
_cell_volume                     1568.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.957
_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  0.0681
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28297
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.475
_diffrn_reflns_theta_min         2.671
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6009
_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_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0494
_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)+(0.0580P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3159
_reflns_number_total             4559
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01972h2.cif
_cod_data_source_block           KB206_0m
_cod_depositor_comments
'Adding full bibliography for 7159103--7159104.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159103
_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   0.975
_shelx_estimated_absorpt_t_max   0.985
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 0.8497(3) 0.3857(2) 0.74196(8) 0.0705(5) Uani 1 1 d . . . . .
H1 H 0.863048 0.362168 0.787006 0.085 Uiso 1 1 calc R U . . .
C2 C 0.7562(2) 0.30667(18) 0.69662(8) 0.0605(4) Uani 1 1 d . . . . .
H2 H 0.706103 0.229826 0.710179 0.073 Uiso 1 1 calc R U . . .
C3 C 0.73786(18) 0.34430(14) 0.62943(7) 0.0449(3) Uani 1 1 d . . . . .
C4 C 0.81425(16) 0.46102(13) 0.61016(6) 0.0396(3) Uani 1 1 d . . . . .
C5 C 0.91000(18) 0.54156(16) 0.65599(7) 0.0499(3) Uani 1 1 d . . . . .
H5 H 0.960845 0.618519 0.642973 0.060 Uiso 1 1 calc R U . . .
C6 C 0.9255(2) 0.5008(2) 0.72216(8) 0.0644(4) Uani 1 1 d . . . . .
H6 H 0.988618 0.552040 0.754463 0.077 Uiso 1 1 calc R U . . .
C7 C 0.66763(15) 0.35540(12) 0.52350(6) 0.0374(3) Uani 1 1 d . . . . .
C8 C 0.59744(16) 0.33399(13) 0.45473(6) 0.0394(3) Uani 1 1 d . . . . .
C9 C 0.49723(17) 0.22322(15) 0.43717(7) 0.0479(3) Uani 1 1 d . . . . .
H9 H 0.476257 0.163016 0.470091 0.058 Uiso 1 1 calc R U . . .
C10 C 0.42878(19) 0.20179(16) 0.37158(8) 0.0556(4) Uani 1 1 d . . . . .
C11 C 0.4629(2) 0.29322(18) 0.32284(8) 0.0591(4) Uani 1 1 d . . . . .
H11 H 0.418746 0.278854 0.278477 0.071 Uiso 1 1 calc R U . . .
C12 C 0.55928(19) 0.40307(17) 0.33851(7) 0.0530(4) Uani 1 1 d . . . . .
H12 H 0.579372 0.462356 0.305058 0.064 Uiso 1 1 calc R U . . .
C13 C 0.62803(16) 0.42649(14) 0.40514(6) 0.0410(3) Uani 1 1 d . . . . .
C14 C 0.3177(3) 0.0836(2) 0.35328(11) 0.0829(6) Uani 1 1 d . . . . .
H14A H 0.200425 0.098715 0.364285 0.124 Uiso 1 1 calc R U . . .
H14B H 0.366243 0.009495 0.377845 0.124 Uiso 1 1 calc R U . . .
H14C H 0.315484 0.067184 0.306049 0.124 Uiso 1 1 calc R U . . .
C15 C 0.72634(16) 0.53950(13) 0.42728(6) 0.0401(3) Uani 1 1 d . . . . .
C16 C 0.79278(15) 0.55846(12) 0.49192(6) 0.0366(3) Uani 1 1 d . . . . .
C17 C 0.88445(17) 0.68741(13) 0.49840(7) 0.0420(3) Uani 1 1 d . . . . .
C18 C 0.76859(18) 0.65765(14) 0.38893(7) 0.0474(3) Uani 1 1 d . . . . .
C19 C 0.9268(2) 0.86838(16) 0.41748(9) 0.0617(4) Uani 1 1 d . . . . .
H19A H 0.960006 0.866813 0.372086 0.074 Uiso 1 1 calc R U . . .
H19B H 1.030297 0.889715 0.447450 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7909(3) 0.97156(18) 0.42264(13) 0.0842(6) Uani 1 1 d . . . . .
H20A H 0.837555 1.054614 0.411436 0.126 Uiso 1 1 calc R U . . .
H20B H 0.758610 0.974170 0.467640 0.126 Uiso 1 1 calc R U . . .
H20C H 0.689350 0.952084 0.392147 0.126 Uiso 1 1 calc R U . . .
N1 N 0.64840(15) 0.28083(12) 0.57527(6) 0.0461(3) Uani 1 1 d . . . . .
N2 N 0.76800(13) 0.46829(10) 0.54076(5) 0.0359(2) Uani 1 1 d . . . . .
N3 N 0.86401(16) 0.73963(12) 0.43445(6) 0.0498(3) Uani 1 1 d . . . . .
O1 O 0.96182(14) 0.73833(11) 0.54695(6) 0.0575(3) Uani 1 1 d . . . . .
O2 O 0.73082(16) 0.68245(12) 0.33060(5) 0.0664(3) 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'
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 121.36(15) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 118.18(17) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
N1 C3 C2 128.25(15) . . ?
N1 C3 C4 111.85(12) . . ?
C2 C3 C4 119.89(14) . . ?
C5 C4 N2 133.44(13) . . ?
C5 C4 C3 122.19(13) . . ?
N2 C4 C3 104.37(11) . . ?
C6 C5 C4 116.22(15) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C5 C6 C1 122.15(16) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
N1 C7 N2 112.82(11) . . ?
N1 C7 C8 127.30(12) . . ?
N2 C7 C8 119.88(11) . . ?
C9 C8 C13 119.80(12) . . ?
C9 C8 C7 120.37(13) . . ?
C13 C8 C7 119.82(12) . . ?
C10 C9 C8 120.95(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.54(14) . . ?
C9 C10 C14 120.64(17) . . ?
C11 C10 C14 120.81(15) . . ?
C12 C11 C10 121.90(14) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.04(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 118.75(13) . . ?
C12 C13 C15 124.63(13) . . ?
C8 C13 C15 116.62(11) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 123.17(12) . . ?
C16 C15 C18 107.22(12) . . ?
C13 C15 C18 129.54(12) . . ?
C15 C16 N2 121.19(12) . . ?
C15 C16 C17 109.65(11) . . ?
N2 C16 C17 129.14(11) . . ?
O1 C17 N3 125.41(14) . . ?
O1 C17 C16 129.84(13) . . ?
N3 C17 C16 104.75(11) . . ?
O2 C18 N3 124.54(14) . . ?
O2 C18 C15 129.12(15) . . ?
N3 C18 C15 106.34(12) . . ?
N3 C19 C20 112.11(14) . . ?
N3 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N3 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C3 105.00(12) . . ?
C16 N2 C4 134.69(11) . . ?
C16 N2 C7 119.28(10) . . ?
C4 N2 C7 105.95(10) . . ?
C17 N3 C18 112.02(12) . . ?
C17 N3 C19 123.96(14) . . ?
C18 N3 C19 123.94(13) . . ?
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 C2 1.365(3) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(2) . ?
C2 H2 0.9300 . ?
C3 N1 1.3856(18) . ?
C3 C4 1.405(2) . ?
C4 C5 1.3884(19) . ?
C4 N2 1.4016(16) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.3098(17) . ?
C7 N2 1.4140(16) . ?
C7 C8 1.4441(18) . ?
C8 C9 1.397(2) . ?
C8 C13 1.411(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(3) . ?
C10 C14 1.506(2) . ?
C11 C12 1.367(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.4051(19) . ?
C12 H12 0.9300 . ?
C13 C15 1.4289(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.3566(18) . ?
C15 C18 1.4891(19) . ?
C16 N2 1.3745(16) . ?
C16 C17 1.4978(19) . ?
C17 O1 1.2055(17) . ?
C17 N3 1.3833(18) . ?
C18 O2 1.2024(17) . ?
C18 N3 1.392(2) . ?
C19 N3 1.4584(19) . ?
C19 C20 1.496(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 N1 -179.37(15) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
N1 C3 C4 C5 179.74(12) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
N1 C3 C4 N2 0.13(14) . . . . ?
C2 C3 C4 N2 -179.18(12) . . . . ?
N2 C4 C5 C6 179.15(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1 C7 C8 C9 -0.43(19) . . . . ?
N2 C7 C8 C9 -179.61(11) . . . . ?
N1 C7 C8 C13 178.61(12) . . . . ?
N2 C7 C8 C13 -0.58(17) . . . . ?
C13 C8 C9 C10 0.74(19) . . . . ?
C7 C8 C9 C10 179.77(12) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C10 C14 -178.70(14) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C14 C10 C11 C12 178.16(15) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C11 C12 C13 C15 -178.27(13) . . . . ?
C9 C8 C13 C12 -1.35(18) . . . . ?
C7 C8 C13 C12 179.61(11) . . . . ?
C9 C8 C13 C15 177.83(11) . . . . ?
C7 C8 C13 C15 -1.21(17) . . . . ?
C12 C13 C15 C16 -179.18(12) . . . . ?
C8 C13 C15 C16 1.70(18) . . . . ?
C12 C13 C15 C18 4.2(2) . . . . ?
C8 C13 C15 C18 -174.93(12) . . . . ?
C13 C15 C16 N2 -0.28(18) . . . . ?
C18 C15 C16 N2 177.00(11) . . . . ?
C13 C15 C16 C17 -178.62(11) . . . . ?
C18 C15 C16 C17 -1.33(13) . . . . ?
C15 C16 C17 O1 -178.78(14) . . . . ?
N2 C16 C17 O1 3.1(2) . . . . ?
C15 C16 C17 N3 0.63(13) . . . . ?
N2 C16 C17 N3 -177.53(12) . . . . ?
C16 C15 C18 O2 -178.22(14) . . . . ?
C13 C15 C18 O2 -1.2(2) . . . . ?
C16 C15 C18 N3 1.55(14) . . . . ?
C13 C15 C18 N3 178.60(12) . . . . ?
N2 C7 N1 C3 0.02(14) . . . . ?
C8 C7 N1 C3 -179.21(12) . . . . ?
C2 C3 N1 C7 179.14(14) . . . . ?
C4 C3 N1 C7 -0.09(15) . . . . ?
C15 C16 N2 C4 -177.99(12) . . . . ?
C17 C16 N2 C4 0.0(2) . . . . ?
C15 C16 N2 C7 -1.62(16) . . . . ?
C17 C16 N2 C7 176.36(11) . . . . ?
C5 C4 N2 C16 -2.9(2) . . . . ?
C3 C4 N2 C16 176.61(12) . . . . ?
C5 C4 N2 C7 -179.66(14) . . . . ?
C3 C4 N2 C7 -0.10(12) . . . . ?
N1 C7 N2 C16 -177.27(10) . . . . ?
C8 C7 N2 C16 2.03(16) . . . . ?
N1 C7 N2 C4 0.05(13) . . . . ?
C8 C7 N2 C4 179.35(10) . . . . ?
O1 C17 N3 C18 179.85(13) . . . . ?
C16 C17 N3 C18 0.40(14) . . . . ?
O1 C17 N3 C19 -3.3(2) . . . . ?
C16 C17 N3 C19 177.29(12) . . . . ?
O2 C18 N3 C17 178.59(13) . . . . ?
C15 C18 N3 C17 -1.19(15) . . . . ?
O2 C18 N3 C19 1.7(2) . . . . ?
C15 C18 N3 C19 -178.08(12) . . . . ?
C20 C19 N3 C17 -91.0(2) . . . . ?
C20 C19 N3 C18 85.5(2) . . . . ?
