#------------------------------------------------------------------------------
#$Date: 2023-08-23 00:56:12 +0300 (Wed, 23 Aug 2023) $
#$Revision: 285830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/20/7132035.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_7132035
loop_
_publ_author_name
'Sarkar, Souradip'
'Biswas, Aniruddha'
'Das, Sarbojit'
'Sanyal, Bortika'
'Sahoo, Rajkumar'
'Samanta, Rajarshi'
_publ_section_title
;
 Weakly Coordinating tert-Amide Assisted Rh(III)-Catalyzed C4-Cyanation of
 Indoles: Application in Photophysical Studies
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03075J
_journal_year                    2023
_chemical_formula_sum            'C21 H17 Cl N3 O'
_chemical_formula_weight         362.83
_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
;
2023-06-02 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                99.80(4)
_cell_angle_beta                 90.05(5)
_cell_angle_gamma                94.96(3)
_cell_formula_units_Z            2
_cell_length_a                   8.059(9)
_cell_length_b                   8.883(10)
_cell_length_c                   12.824(18)
_cell_measurement_reflns_used    5203
_cell_measurement_temperature    274(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     901.1(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      274(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37573
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_min         2.537
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7239
_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            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0494
_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)+(0.0650P)²+0.2887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4080
_reflns_number_total             5203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03075j2.cif
_cod_data_source_block           shelx
_cod_database_code               7132035
_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.
;
_exptl_absorpt_special_details   'SADABS 2.10 (Bruker 2003)'
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
Cl1 Cl 0.26974(7) 0.35863(6) 0.60063(4) 0.06386(16) Uani 1 1 d . . . . .
O1 O 0.41993(15) 0.74824(16) 0.08040(11) 0.0605(3) Uani 1 1 d . . . . .
N1 N 0.40894(15) 0.31658(14) 0.20024(10) 0.0418(3) Uani 1 1 d . . . . .
N2 N 0.15143(16) 0.71934(16) 0.12641(11) 0.0461(3) Uani 1 1 d . . . . .
C8 C 0.31697(15) 0.53404(16) 0.28874(11) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.35880(16) 0.38529(16) 0.29854(12) 0.0369(3) Uani 1 1 d . . . . .
C6 C 0.34647(17) 0.32828(16) 0.39347(12) 0.0405(3) Uani 1 1 d . . . . .
H007 H 0.374149 0.230104 0.398057 0.049 Uiso 1 1 calc R U . . .
C9 C 0.30907(18) 0.68097(17) 0.12553(11) 0.0399(3) Uani 1 1 d . . . . .
C15 C 0.63614(17) 0.15617(16) 0.22740(12) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.27006(18) 0.62992(16) 0.38134(12) 0.0394(3) Uani 1 1 d . . . . .
C4 C 0.25581(19) 0.57458(18) 0.47667(12) 0.0438(3) Uani 1 1 d . . . . .
H00B H 0.222952 0.637150 0.537450 0.053 Uiso 1 1 calc R U . . .
N3 N 0.2383(3) 0.91507(19) 0.37813(15) 0.0711(5) Uani 1 1 d . . . . .
C1 C 0.40024(17) 0.41663(18) 0.13067(12) 0.0432(3) Uani 1 1 d . . . . .
H00D H 0.429643 0.396612 0.059872 0.052 Uiso 1 1 calc R U . . .
C2 C 0.34200(17) 0.55068(17) 0.18019(12) 0.0395(3) Uani 1 1 d . . . . .
C5 C 0.29140(19) 0.42412(17) 0.48007(12) 0.0428(3) Uani 1 1 d . . . . .
C14 C 0.46896(19) 0.16349(18) 0.17607(15) 0.0491(4) Uani 1 1 d . . . . .
H00A H 0.477883 0.134686 0.099987 0.059 Uiso 1 1 calc R U . . .
H00C H 0.388338 0.089982 0.200273 0.059 Uiso 1 1 calc R U . . .
C21 C 0.2483(2) 0.78873(18) 0.37986(13) 0.0475(4) Uani 1 1 d . . . . .
C16 C 0.7700(2) 0.25684(19) 0.21081(15) 0.0511(4) Uani 1 1 d . . . . .
H00I H 0.756889 0.330470 0.168564 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6587(2) 0.04864(18) 0.29183(16) 0.0526(4) Uani 1 1 d . . . . .
H00J H 0.569567 -0.019646 0.303930 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1028(2) 0.8453(2) 0.07607(15) 0.0546(4) Uani 1 1 d . . . . .
H00E H 0.158578 0.845755 0.009134 0.066 Uiso 1 1 calc R U . . .
H00F H 0.130502 0.943281 0.121532 0.066 Uiso 1 1 calc R U . . .
C18 C 0.9448(2) 0.1412(2) 0.32026(16) 0.0574(4) Uani 1 1 d . . . . .
H00L H 1.048576 0.136240 0.350702 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8127(2) 0.0419(2) 0.33835(16) 0.0594(4) Uani 1 1 d . . . . .
H00M H 0.826151 -0.030090 0.381833 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9232(2) 0.2486(2) 0.25672(18) 0.0609(5) Uani 1 1 d . . . . .
H00N H 1.012877 0.316272 0.244599 0.073 Uiso 1 1 calc R U . . .
C13 C 0.0056(2) 0.6350(3) 0.16324(19) 0.0676(6) Uani 1 1 d . . . . .
H00G H 0.010397 0.525419 0.141649 0.081 Uiso 1 1 calc R U . . .
H00H H -0.000648 0.657669 0.239768 0.081 Uiso 1 1 calc R U . . .
C11 C -0.0821(3) 0.8152(3) 0.05923(19) 0.0684(5) Uani 1 1 d . . . . .
H00K H -0.136992 0.905849 0.088043 0.082 Uiso 1 1 calc R U . . .
H00O H -0.108972 0.788336 -0.015742 0.082 Uiso 1 1 calc R U . . .
C12 C -0.1376(3) 0.6864(3) 0.1144(3) 0.0914(9) Uani 1 1 d . . . . .
H00Q H -0.247102 0.644785 0.117315 0.110 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C7 109.07(15) . . ?
C1 N1 C14 125.71(15) . . ?
C7 N1 C14 125.16(14) . . ?
C9 N2 C13 126.61(15) . . ?
C9 N2 C10 121.98(13) . . ?
C13 N2 C10 110.99(14) . . ?
C3 C8 C7 117.49(14) . . ?
C3 C8 C2 135.33(14) . . ?
C7 C8 C2 107.11(13) . . ?
N1 C7 C6 129.87(15) . . ?
N1 C7 C8 107.18(14) . . ?
C6 C7 C8 122.94(14) . . ?
C5 C6 C7 116.97(15) . . ?
C5 C6 H007 121.5 . . ?
C7 C6 H007 121.5 . . ?
O1 C9 N2 121.60(15) . . ?
O1 C9 C2 121.84(14) . . ?
N2 C9 C2 116.55(13) . . ?
C16 C15 C20 118.68(15) . . ?
C16 C15 C14 120.36(16) . . ?
C20 C15 C14 120.96(15) . . ?
C4 C3 C8 120.26(15) . . ?
C4 C3 C21 119.38(14) . . ?
C8 C3 C21 120.21(14) . . ?
C3 C4 C5 119.40(15) . . ?
C3 C4 H00B 120.3 . . ?
C5 C4 H00B 120.3 . . ?
N1 C1 C2 110.35(16) . . ?
N1 C1 H00D 124.8 . . ?
C2 C1 H00D 124.8 . . ?
C1 C2 C8 106.26(14) . . ?
C1 C2 C9 124.11(16) . . ?
C8 C2 C9 129.60(14) . . ?
C6 C5 C4 122.76(15) . . ?
C6 C5 Cl1 119.27(14) . . ?
C4 C5 Cl1 117.95(13) . . ?
N1 C14 C15 112.46(13) . . ?
N1 C14 H00A 109.1 . . ?
C15 C14 H00A 109.1 . . ?
N1 C14 H00C 109.1 . . ?
C15 C14 H00C 109.1 . . ?
H00A C14 H00C 107.8 . . ?
N3 C21 C3 177.05(19) . . ?
C17 C16 C15 120.23(17) . . ?
C17 C16 H00I 119.9 . . ?
C15 C16 H00I 119.9 . . ?
C19 C20 C15 120.73(16) . . ?
C19 C20 H00J 119.6 . . ?
C15 C20 H00J 119.6 . . ?
N2 C10 C11 105.07(15) . . ?
N2 C10 H00E 110.7 . . ?
C11 C10 H00E 110.7 . . ?
N2 C10 H00F 110.7 . . ?
C11 C10 H00F 110.7 . . ?
H00E C10 H00F 108.8 . . ?
C19 C18 C17 119.59(17) . . ?
C19 C18 H00L 120.2 . . ?
C17 C18 H00L 120.2 . . ?
C18 C19 C20 119.99(17) . . ?
C18 C19 H00M 120.0 . . ?
C20 C19 H00M 120.0 . . ?
C18 C17 C16 120.77(17) . . ?
C18 C17 H00N 119.6 . . ?
C16 C17 H00N 119.6 . . ?
C12 C13 N2 105.64(17) . . ?
C12 C13 H00G 110.6 . . ?
N2 C13 H00G 110.6 . . ?
C12 C13 H00H 110.6 . . ?
N2 C13 H00H 110.6 . . ?
H00G C13 H00H 108.7 . . ?
C12 C11 C10 107.08(15) . . ?
C12 C11 H00K 110.3 . . ?
C10 C11 H00K 110.3 . . ?
C12 C11 H00O 110.3 . . ?
C10 C11 H00O 110.3 . . ?
H00K C11 H00O 108.6 . . ?
C13 C12 C11 109.55(18) . . ?
C13 C12 H00Q 125.2 . . ?
C11 C12 H00Q 125.2 . . ?
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
Cl1 C5 1.746(3) . ?
O1 C9 1.231(2) . ?
N1 C1 1.368(2) . ?
N1 C7 1.381(2) . ?
N1 C14 1.466(2) . ?
N2 C9 1.343(2) . ?
N2 C13 1.461(2) . ?
N2 C10 1.464(2) . ?
C8 C3 1.411(2) . ?
C8 C7 1.417(2) . ?
C8 C2 1.437(3) . ?
C7 C6 1.396(3) . ?
C6 C5 1.378(3) . ?
C6 H007 0.9300 . ?
C9 C2 1.493(2) . ?
C15 C16 1.381(2) . ?
C15 C20 1.388(3) . ?
C15 C14 1.510(3) . ?
C3 C4 1.394(3) . ?
C3 C21 1.440(3) . ?
C4 C5 1.399(3) . ?
C4 H00B 0.9300 . ?
N3 C21 1.136(2) . ?
C1 C2 1.372(2) . ?
C1 H00D 0.9300 . ?
C14 H00A 0.9700 . ?
C14 H00C 0.9700 . ?
C16 C17 1.380(3) . ?
C16 H00I 0.9300 . ?
C20 C19 1.387(3) . ?
C20 H00J 0.9300 . ?
C10 C11 1.499(3) . ?
C10 H00E 0.9700 . ?
C10 H00F 0.9700 . ?
C18 C19 1.369(3) . ?
C18 C17 1.377(3) . ?
C18 H00L 0.9300 . ?
C19 H00M 0.9300 . ?
C17 H00N 0.9300 . ?
C13 C12 1.456(3) . ?
C13 H00G 0.9700 . ?
C13 H00H 0.9700 . ?
C11 C12 1.483(3) . ?
C11 H00K 0.9700 . ?
C11 H00O 0.9700 . ?
C12 H00Q 0.9300 . ?
