#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/37/7123788.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_7123788
loop_
_publ_author_name
'Shang, Yaping'
'Jonnada, Krishna'
'Yedage, Subhash L.'
'Tu, Hua'
'Zhang, Xiaofeng'
'Lou, Xin'
'Huang, Shijun'
'Su, Weiping'
_publ_section_title
;
 Rhodium(III)-Catalyzed Indole Synthesis at Room Temperature Using the
 Transient Oxidizing Directing Group Strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04529E
_journal_year                    2019
_chemical_formula_moiety         'C21 H16 F N'
_chemical_formula_sum            'C21 H16 F N'
_chemical_formula_weight         301.35
_chemical_name_systematic        4-fluoro-1-methyl-2,3-diphenyl-1H-indole
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-03-27 deposited with the CCDC.    2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                74.507(3)
_cell_angle_beta                 77.133(3)
_cell_angle_gamma                80.906(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8096(5)
_cell_length_b                   9.0152(5)
_cell_length_c                   10.3747(6)
_cell_measurement_reflns_used    9394
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.36
_cell_volume                     769.81(8)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      160(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31578
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.303
_refine_ls_extinction_coef       0.23(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0987P)²+0.3444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1832
_reflns_number_gt                2868
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc04529e2.cif
_cod_data_source_block           3ab
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7123788
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.16585(12) 0.27070(14) 0.73123(11) 0.0329(3) Uani 1 1 d .
N1 N 0.70036(17) 0.19862(17) 0.57272(14) 0.0231(3) Uani 1 1 d .
C1 C 0.5909(2) 0.20780(19) 0.68865(17) 0.0226(4) Uani 1 1 d .
C2 C 0.4411(2) 0.23904(18) 0.65267(17) 0.0215(4) Uani 1 1 d .
C3 C 0.46398(19) 0.25004(18) 0.50902(16) 0.0211(4) Uani 1 1 d .
C4 C 0.62321(19) 0.22378(18) 0.46453(16) 0.0209(4) Uani 1 1 d .
C5 C 0.3134(2) 0.2457(2) 0.75881(18) 0.0249(4) Uani 1 1 d .
C6 C 0.3308(2) 0.2282(2) 0.89050(18) 0.0301(4) Uani 1 1 d .
H6A H 0.2414 0.2343 0.9604 0.036 Uiso 1 1 calc R
C7 C 0.4815(2) 0.2014(2) 0.92104(19) 0.0327(4) Uani 1 1 d .
H7A H 0.4933 0.1911 1.0119 0.039 Uiso 1 1 calc R
C8 C 0.6129(2) 0.1895(2) 0.82180(18) 0.0288(4) Uani 1 1 d .
H8A H 0.7148 0.1697 0.8430 0.035 Uiso 1 1 calc R
C9 C 0.8679(2) 0.1690(2) 0.56870(19) 0.0282(4) Uani 1 1 d .
H9A H 0.8890 0.1558 0.6602 0.042 Uiso 1 1 calc R
H9B H 0.9197 0.2566 0.5062 0.042 Uiso 1 1 calc R
H9C H 0.9083 0.0746 0.5370 0.042 Uiso 1 1 calc R
C10 C 0.70768(19) 0.2266(2) 0.32383(17) 0.0227(4) Uani 1 1 d .
C11 C 0.8062(2) 0.0990(2) 0.29150(19) 0.0276(4) Uani 1 1 d .
H11A H 0.8210 0.0079 0.3610 0.033 Uiso 1 1 calc R
C12 C 0.8827(2) 0.1049(2) 0.1580(2) 0.0335(4) Uani 1 1 d .
H12A H 0.9506 0.0181 0.1369 0.040 Uiso 1 1 calc R
C13 C 0.8606(2) 0.2367(3) 0.05526(19) 0.0342(5) Uani 1 1 d .
H13A H 0.9139 0.2406 -0.0357 0.041 Uiso 1 1 calc R
C14 C 0.7604(2) 0.3628(2) 0.08604(19) 0.0347(5) Uani 1 1 d .
H14A H 0.7435 0.4525 0.0157 0.042 Uiso 1 1 calc R
C15 C 0.6845(2) 0.3582(2) 0.21985(19) 0.0283(4) Uani 1 1 d .
H15A H 0.6165 0.4451 0.2405 0.034 Uiso 1 1 calc R
C16 C 0.34479(19) 0.28271(19) 0.42273(16) 0.0215(4) Uani 1 1 d .
C17 C 0.3421(2) 0.1861(2) 0.33821(17) 0.0245(4) Uani 1 1 d .
H17A H 0.4158 0.0969 0.3384 0.029 Uiso 1 1 calc R
C18 C 0.2326(2) 0.2193(2) 0.25388(18) 0.0289(4) Uani 1 1 d .
H18A H 0.2316 0.1523 0.1974 0.035 Uiso 1 1 calc R
C19 C 0.1250(2) 0.3494(2) 0.25155(19) 0.0326(5) Uani 1 1 d .
H19A H 0.0508 0.3720 0.1933 0.039 Uiso 1 1 calc R
C20 C 0.1264(2) 0.4464(2) 0.3350(2) 0.0326(4) Uani 1 1 d .
H20A H 0.0529 0.5358 0.3338 0.039 Uiso 1 1 calc R
C21 C 0.2350(2) 0.4132(2) 0.42049(18) 0.0273(4) Uani 1 1 d .
H21A H 0.2346 0.4798 0.4778 0.033 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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
C1 N1 C4 108.70(14)
C1 N1 C9 124.02(14)
C4 N1 C9 127.28(15)
N1 C1 C8 129.35(16)
N1 C1 C2 107.78(14)
C8 C1 C2 122.87(16)
C5 C2 C1 116.29(15)
C5 C2 C3 136.33(16)
C1 C2 C3 107.33(15)
C4 C3 C2 106.32(14)
C4 C3 C16 125.37(15)
C2 C3 C16 128.31(15)
C3 C4 N1 109.87(15)
C3 C4 C10 127.66(15)
N1 C4 C10 122.42(15)
F1 C5 C6 118.67(16)
F1 C5 C2 119.03(15)
C6 C5 C2 122.30(17)
C5 C6 C7 119.51(17)
C5 C6 H6A 120.2
C7 C6 H6A 120.2
C8 C7 C6 121.31(17)
C8 C7 H7A 119.3
C6 C7 H7A 119.3
C7 C8 C1 117.67(17)
C7 C8 H8A 121.2
C1 C8 H8A 121.2
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 119.11(16)
C11 C10 C4 121.65(15)
C15 C10 C4 119.21(16)
C12 C11 C10 120.21(17)
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C13 C12 C11 120.43(18)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C14 C13 C12 119.73(17)
C14 C13 H13A 120.1
C12 C13 H13A 120.1
C13 C14 C15 120.11(18)
C13 C14 H14A 119.9
C15 C14 H14A 119.9
C14 C15 C10 120.39(18)
C14 C15 H15A 119.8
C10 C15 H15A 119.8
C17 C16 C21 118.58(16)
C17 C16 C3 120.52(15)
C21 C16 C3 120.87(15)
C18 C17 C16 120.54(17)
C18 C17 H17A 119.7
C16 C17 H17A 119.7
C19 C18 C17 120.53(17)
C19 C18 H18A 119.7
C17 C18 H18A 119.7
C18 C19 C20 119.51(17)
C18 C19 H19A 120.2
C20 C19 H19A 120.2
C21 C20 C19 120.28(18)
C21 C20 H20A 119.9
C19 C20 H20A 119.9
C20 C21 C16 120.55(17)
C20 C21 H21A 119.7
C16 C21 H21A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.365(2)
N1 C1 1.376(2)
N1 C4 1.389(2)
N1 C9 1.451(2)
C1 C8 1.400(2)
C1 C2 1.416(2)
C2 C5 1.394(2)
C2 C3 1.437(2)
C3 C4 1.379(2)
C3 C16 1.473(2)
C4 C10 1.479(2)
C5 C6 1.373(3)
C6 C7 1.402(3)
C6 H6A 0.9500
C7 C8 1.378(3)
C7 H7A 0.9500
C8 H8A 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.396(2)
C10 C15 1.397(2)
C11 C12 1.390(3)
C11 H11A 0.9500
C12 C13 1.389(3)
C12 H12A 0.9500
C13 C14 1.388(3)
C13 H13A 0.9500
C14 C15 1.393(3)
C14 H14A 0.9500
C15 H15A 0.9500
C16 C17 1.397(2)
C16 C21 1.399(2)
C17 C18 1.389(2)
C17 H17A 0.9500
C18 C19 1.385(3)
C18 H18A 0.9500
C19 C20 1.388(3)
C19 H19A 0.9500
C20 C21 1.392(3)
C20 H20A 0.9500
C21 H21A 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
C4 N1 C1 C8 179.53(17)
C9 N1 C1 C8 -1.1(3)
C4 N1 C1 C2 0.18(18)
C9 N1 C1 C2 179.55(15)
N1 C1 C2 C5 177.24(14)
C8 C1 C2 C5 -2.2(3)
N1 C1 C2 C3 -0.54(18)
C8 C1 C2 C3 -179.94(15)
C5 C2 C3 C4 -176.43(19)
C1 C2 C3 C4 0.69(18)
C5 C2 C3 C16 3.6(3)
C1 C2 C3 C16 -179.25(16)
C2 C3 C4 N1 -0.59(18)
C16 C3 C4 N1 179.35(15)
C2 C3 C4 C10 -178.22(16)
C16 C3 C4 C10 1.7(3)
C1 N1 C4 C3 0.27(19)
C9 N1 C4 C3 -179.08(16)
C1 N1 C4 C10 178.05(15)
C9 N1 C4 C10 -1.3(3)
C1 C2 C5 F1 -178.00(14)
C3 C2 C5 F1 -1.1(3)
C1 C2 C5 C6 2.1(3)
C3 C2 C5 C6 178.99(18)
F1 C5 C6 C7 179.54(17)
C2 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 -1.1(3)
C6 C7 C8 C1 1.0(3)
N1 C1 C8 C7 -178.59(18)
C2 C1 C8 C7 0.7(3)
C3 C4 C10 C11 -123.1(2)
N1 C4 C10 C11 59.5(2)
C3 C4 C10 C15 54.8(2)
N1 C4 C10 C15 -122.58(18)
C15 C10 C11 C12 1.5(3)
C4 C10 C11 C12 179.39(16)
C10 C11 C12 C13 -0.8(3)
C11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 1.2(3)
C13 C14 C15 C10 -0.4(3)
C11 C10 C15 C14 -0.9(3)
C4 C10 C15 C14 -178.83(16)
C4 C3 C16 C17 51.4(2)
C2 C3 C16 C17 -128.65(19)
C4 C3 C16 C21 -126.64(19)
C2 C3 C16 C21 53.3(2)
C21 C16 C17 C18 0.0(3)
C3 C16 C17 C18 -178.12(15)
C16 C17 C18 C19 0.4(3)
C17 C18 C19 C20 -0.4(3)
C18 C19 C20 C21 0.0(3)
C19 C20 C21 C16 0.5(3)
C17 C16 C21 C20 -0.5(3)
C3 C16 C21 C20 177.65(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350820
