#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:29:16 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158015.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_7158015
loop_
_publ_author_name
'Jin, Jiang'
'Li, Yinghua'
'Xiang, Shiqun'
'Fan, Weibin'
'Guo, Shiwei'
'Huang, Deguang'
_publ_section_title
;
 Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using
 methyl tert-butyl ether as a new methylene precursor.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4076
_journal_page_last               4081
_journal_paper_doi               10.1039/d1ob00120e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C21 H20 F2 N2'
_chemical_formula_sum            'C21 H20 F2 N2'
_chemical_formula_weight         338.39
_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
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                86.424(5)
_cell_angle_beta                 84.971(6)
_cell_angle_gamma                85.252(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9071(6)
_cell_length_b                   8.9267(5)
_cell_length_c                   11.6792(7)
_cell_measurement_reflns_used    2659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4020
_cell_measurement_theta_min      3.7650
_cell_volume                     817.11(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5413
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.939
_diffrn_reflns_theta_min         3.805
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0048(17)
_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   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0605
_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)+(0.0993P)²+0.7951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2619
_reflns_number_total             3056
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00120e2.cif
_cod_data_source_block           Compound3l
_cod_depositor_comments
'Adding full bibliography for 7158011--7158015.cif.'
_cod_database_code               7158015
_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   0.857
_shelx_estimated_absorpt_t_max   0.890
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
F1 F -0.0439(2) 0.34589(19) 0.64266(13) 0.0407(4) Uani 1 1 d . . . . .
F2 F 0.02819(19) 0.09854(19) 0.14554(14) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.6189(3) 0.1547(2) 0.53481(16) 0.0262(5) Uani 1 1 d . . . . .
N2 N 0.6411(3) 0.3226(2) 0.01890(16) 0.0248(5) Uani 1 1 d . . . . .
C1 C 0.6559(3) 0.2474(3) 0.43785(19) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.5125(3) 0.3363(3) 0.41163(19) 0.0228(5) Uani 1 1 d . . . . .
C3 C 0.3803(3) 0.2998(2) 0.49795(19) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.2108(3) 0.3553(3) 0.5209(2) 0.0259(5) Uani 1 1 d . . . . .
H4A H 0.159517 0.433456 0.473457 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1219(3) 0.2911(3) 0.6157(2) 0.0300(6) Uani 1 1 d . . . . .
C6 C 0.1871(3) 0.1746(3) 0.6876(2) 0.0318(6) Uani 1 1 d . . . . .
H6A H 0.117799 0.133805 0.750566 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3553(3) 0.1188(3) 0.6660(2) 0.0294(6) Uani 1 1 d . . . . .
H7A H 0.403617 0.038762 0.713163 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4511(3) 0.1839(3) 0.5730(2) 0.0247(5) Uani 1 1 d . . . . .
C9 C 0.7376(4) 0.0476(3) 0.5915(2) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.849576 0.046528 0.548205 0.052 Uiso 1 1 calc R U . . .
H9B H 0.747143 0.077270 0.669888 0.052 Uiso 1 1 calc R U . . .
H9C H 0.695980 -0.053058 0.594477 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8297(3) 0.2430(3) 0.3777(2) 0.0317(6) Uani 1 1 d . . . . .
H10A H 0.904680 0.167563 0.417153 0.047 Uiso 1 1 calc R U . . .
H10B H 0.824751 0.216471 0.297949 0.047 Uiso 1 1 calc R U . . .
H10C H 0.874356 0.342136 0.378279 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4974(3) 0.4514(3) 0.31133(19) 0.0234(5) Uani 1 1 d . . . . .
H11A H 0.382627 0.505017 0.318732 0.028 Uiso 1 1 calc R U . . .
H11B H 0.581565 0.526486 0.316104 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6610(3) 0.4017(3) 0.11440(19) 0.0230(5) Uani 1 1 d . . . . .
C13 C 0.5252(3) 0.3861(2) 0.19450(19) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.4130(3) 0.2938(2) 0.14611(19) 0.0208(5) Uani 1 1 d . . . . .
C15 C 0.2537(3) 0.2408(3) 0.1840(2) 0.0242(5) Uani 1 1 d . . . . .
H15A H 0.197465 0.264660 0.256609 0.029 Uiso 1 1 calc R U . . .
C16 C 0.1831(3) 0.1528(3) 0.1110(2) 0.0279(6) Uani 1 1 d . . . . .
C17 C 0.2573(3) 0.1156(3) 0.0030(2) 0.0295(6) Uani 1 1 d . . . . .
H17A H 0.201550 0.055145 -0.043764 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4126(3) 0.1676(3) -0.0353(2) 0.0279(6) Uani 1 1 d . . . . .
H18A H 0.466172 0.143836 -0.108654 0.034 Uiso 1 1 calc R U . . .
C19 C 0.4894(3) 0.2562(3) 0.03662(19) 0.0232(5) Uani 1 1 d . . . . .
C20 C 0.7588(3) 0.3097(3) -0.0841(2) 0.0321(6) Uani 1 1 d . . . . .
H20A H 0.857487 0.366775 -0.076380 0.048 Uiso 1 1 calc DR U . . .
H20B H 0.796896 0.203561 -0.093515 0.048 Uiso 1 1 calc R U . . .
H20C H 0.701092 0.350104 -0.151628 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8150(3) 0.4893(3) 0.1180(2) 0.0290(6) Uani 1 1 d . . . . .
H21A H 0.888902 0.477286 0.046780 0.043 Uiso 1 1 calc DR U . . .
H21B H 0.778586 0.596135 0.125570 0.043 Uiso 1 1 calc R U . . .
H21C H 0.877738 0.451615 0.183990 0.043 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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C8 N1 C1 108.88(19) . . ?
C8 N1 C9 124.5(2) . . ?
C1 N1 C9 126.5(2) . . ?
C19 N2 C12 108.40(19) . . ?
C19 N2 C20 124.8(2) . . ?
C12 N2 C20 126.8(2) . . ?
C2 C1 N1 109.8(2) . . ?
C2 C1 C10 128.8(2) . . ?
N1 C1 C10 121.4(2) . . ?
C1 C2 C3 106.7(2) . . ?
C1 C2 C11 126.8(2) . . ?
C3 C2 C11 126.6(2) . . ?
C4 C3 C8 119.1(2) . . ?
C4 C3 C2 133.8(2) . . ?
C8 C3 C2 107.0(2) . . ?
C5 C4 C3 116.8(2) . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 H4A 121.6 . . ?
F1 C5 C4 118.3(2) . . ?
F1 C5 C6 116.8(2) . . ?
C4 C5 C6 124.9(2) . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C8 117.9(2) . . ?
C6 C7 H7A 121.0 . . ?
C8 C7 H7A 121.0 . . ?
N1 C8 C7 130.1(2) . . ?
N1 C8 C3 107.6(2) . . ?
C7 C8 C3 122.3(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 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C2 114.42(19) . . ?
C13 C11 H11A 108.7 . . ?
C2 C11 H11A 108.7 . . ?
C13 C11 H11B 108.7 . . ?
C2 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 N2 110.1(2) . . ?
C13 C12 C21 129.7(2) . . ?
N2 C12 C21 120.2(2) . . ?
C12 C13 C14 106.5(2) . . ?
C12 C13 C11 127.5(2) . . ?
C14 C13 C11 126.0(2) . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 C13 134.0(2) . . ?
C19 C14 C13 107.0(2) . . ?
C16 C15 C14 116.9(2) . . ?
C16 C15 H15A 121.5 . . ?
C14 C15 H15A 121.5 . . ?
F2 C16 C15 118.4(2) . . ?
F2 C16 C17 117.1(2) . . ?
C15 C16 C17 124.5(2) . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17A 120.4 . . ?
C16 C17 H17A 120.4 . . ?
C17 C18 C19 118.2(2) . . ?
C17 C18 H18A 120.9 . . ?
C19 C18 H18A 120.9 . . ?
N2 C19 C18 129.8(2) . . ?
N2 C19 C14 107.9(2) . . ?
C18 C19 C14 122.3(2) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
F1 C5 1.377(3) . ?
F2 C16 1.373(3) . ?
N1 C8 1.371(3) . ?
N1 C1 1.385(3) . ?
N1 C9 1.454(3) . ?
N2 C19 1.375(3) . ?
N2 C12 1.384(3) . ?
N2 C20 1.460(3) . ?
C1 C2 1.375(3) . ?
C1 C10 1.486(3) . ?
C2 C3 1.430(3) . ?
C2 C11 1.515(3) . ?
C3 C4 1.399(3) . ?
C3 C8 1.424(3) . ?
C4 C5 1.378(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(4) . ?
C6 C7 1.388(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.371(3) . ?
C12 C21 1.506(3) . ?
C13 C14 1.433(3) . ?
C14 C15 1.408(3) . ?
C14 C19 1.413(3) . ?
C15 C16 1.376(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(4) . ?
C17 C18 1.377(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.397(3) . ?
C18 H18A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
C8 N1 C1 C2 -0.6(3) . . . . ?
C9 N1 C1 C2 -178.2(2) . . . . ?
C8 N1 C1 C10 179.1(2) . . . . ?
C9 N1 C1 C10 1.5(4) . . . . ?
N1 C1 C2 C3 1.3(2) . . . . ?
C10 C1 C2 C3 -178.4(2) . . . . ?
N1 C1 C2 C11 -179.1(2) . . . . ?
C10 C1 C2 C11 1.3(4) . . . . ?
C1 C2 C3 C4 176.8(2) . . . . ?
C11 C2 C3 C4 -2.8(4) . . . . ?
C1 C2 C3 C8 -1.6(2) . . . . ?
C11 C2 C3 C8 178.8(2) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 F1 178.23(19) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
F1 C5 C6 C7 -178.0(2) . . . . ?
C4 C5 C6 C7 1.6(4) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C1 N1 C8 C7 179.3(2) . . . . ?
C9 N1 C8 C7 -3.1(4) . . . . ?
C1 N1 C8 C3 -0.5(2) . . . . ?
C9 N1 C8 C3 177.2(2) . . . . ?
C6 C7 C8 N1 177.7(2) . . . . ?
C6 C7 C8 C3 -2.6(3) . . . . ?
C4 C3 C8 N1 -177.39(19) . . . . ?
C2 C3 C8 N1 1.2(2) . . . . ?
C4 C3 C8 C7 2.9(3) . . . . ?
C2 C3 C8 C7 -178.5(2) . . . . ?
C1 C2 C11 C13 63.9(3) . . . . ?
C3 C2 C11 C13 -116.5(2) . . . . ?
C19 N2 C12 C13 0.7(3) . . . . ?
C20 N2 C12 C13 -179.2(2) . . . . ?
C19 N2 C12 C21 -178.6(2) . . . . ?
C20 N2 C12 C21 1.5(3) . . . . ?
N2 C12 C13 C14 -0.7(2) . . . . ?
C21 C12 C13 C14 178.5(2) . . . . ?
N2 C12 C13 C11 178.9(2) . . . . ?
C21 C12 C13 C11 -1.9(4) . . . . ?
C2 C11 C13 C12 -109.7(3) . . . . ?
C2 C11 C13 C14 69.8(3) . . . . ?
C12 C13 C14 C15 -178.4(2) . . . . ?
C11 C13 C14 C15 1.9(4) . . . . ?
C12 C13 C14 C19 0.5(2) . . . . ?
C11 C13 C14 C19 -179.1(2) . . . . ?
C19 C14 C15 C16 0.8(3) . . . . ?
C13 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 F2 179.7(2) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
F2 C16 C17 C18 180.0(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C12 N2 C19 C18 178.9(2) . . . . ?
C20 N2 C19 C18 -1.2(4) . . . . ?
C12 N2 C19 C14 -0.4(2) . . . . ?
C20 N2 C19 C14 179.6(2) . . . . ?
C17 C18 C19 N2 -179.3(2) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C15 C14 C19 N2 179.04(19) . . . . ?
C13 C14 C19 N2 -0.1(2) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C13 C14 C19 C18 -179.4(2) . . . . ?
