#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:29:16 +0200 (Sat 05 de Jun de 2021) $
#$Revision: 266172 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/80/7158013.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_7158013
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 Cl2 N2'
_chemical_formula_sum            'C21 H20 Cl2 N2'
_chemical_formula_weight         371.29
_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                110.640(5)
_cell_angle_beta                 90.771(4)
_cell_angle_gamma                112.601(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8647(5)
_cell_length_b                   10.0294(6)
_cell_length_c                   11.7597(5)
_cell_measurement_reflns_used    2922
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.2960
_cell_measurement_theta_min      4.0470
_cell_volume                     889.76(10)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6815
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.924
_diffrn_reflns_theta_min         4.078
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75052
_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    1.386
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0486
_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)+(0.0859P)²+0.7289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2884
_reflns_number_total             3346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00120e2.cif
_cod_data_source_block           Compound3m
_cod_depositor_comments
'Adding full bibliography for 7158011--7158015.cif.'
_cod_original_cell_volume        889.76(9)
_cod_database_code               7158013
_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   0.557
_shelx_estimated_absorpt_t_max   0.733
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 0.47277(8) 1.03059(8) 0.66148(6) 0.0354(2) Uani 1 1 d . . . . .
Cl2 Cl 0.27713(9) 0.01264(8) -0.05341(6) 0.0348(2) Uani 1 1 d . . . . .
N1 N 0.2666(3) 0.3603(3) 0.5326(2) 0.0299(5) Uani 1 1 d . . . . .
N2 N 0.2051(3) 0.6018(2) 0.0886(2) 0.0271(5) Uani 1 1 d . . . . .
C1 C 0.1441(3) 0.3009(3) 0.4301(2) 0.0289(6) Uani 1 1 d . . . . .
C2 C 0.1360(3) 0.4219(3) 0.4057(2) 0.0257(5) Uani 1 1 d . . . . .
C3 C 0.2558(3) 0.5640(3) 0.4981(2) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.2984(3) 0.7225(3) 0.5252(2) 0.0259(5) Uani 1 1 d . . . . .
H4A H 0.247421 0.754584 0.474525 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4165(3) 0.8311(3) 0.6276(2) 0.0280(6) Uani 1 1 d . . . . .
C6 C 0.4952(3) 0.7890(4) 0.7047(2) 0.0330(6) Uani 1 1 d . . . . .
H6A H 0.575757 0.867808 0.774590 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4555(3) 0.6329(4) 0.6790(2) 0.0323(6) Uani 1 1 d . . . . .
H7A H 0.508312 0.602619 0.730078 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3353(3) 0.5206(3) 0.5758(2) 0.0278(5) Uani 1 1 d . . . . .
C9 C 0.3178(4) 0.2686(4) 0.5835(3) 0.0367(7) Uani 1 1 d . . . . .
H9A H 0.249740 0.156839 0.536575 0.055 Uiso 1 1 calc R U . . .
H9B H 0.434747 0.291308 0.578232 0.055 Uiso 1 1 calc R U . . .
H9C H 0.303517 0.295861 0.670047 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0460(4) 0.1283(3) 0.3653(3) 0.0392(7) Uani 1 1 d . . . . .
H10A H 0.082853 0.073657 0.406305 0.059 Uiso 1 1 calc R U . . .
H10B H -0.071948 0.102841 0.367657 0.059 Uiso 1 1 calc R U . . .
H10C H 0.062803 0.095231 0.279253 0.059 Uiso 1 1 calc R U . . .
C11 C 0.0207(3) 0.4137(3) 0.3058(2) 0.0271(5) Uani 1 1 d . . . . .
H11A H -0.063228 0.304315 0.264745 0.032 Uiso 1 1 calc R U . . .
H11B H -0.038640 0.479497 0.344421 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1254(3) 0.5986(3) 0.1891(2) 0.0256(5) Uani 1 1 d . . . . .
C13 C 0.1045(3) 0.4662(3) 0.2093(2) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.1727(3) 0.3814(3) 0.1160(2) 0.0227(5) Uani 1 1 d . . . . .
C15 C 0.1849(3) 0.2376(3) 0.0860(2) 0.0247(5) Uani 1 1 d . . . . .
H15A H 0.144744 0.175738 0.133490 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2572(3) 0.1895(3) -0.0146(2) 0.0260(5) Uani 1 1 d . . . . .
C17 C 0.3172(3) 0.2762(3) -0.0878(2) 0.0282(6) Uani 1 1 d . . . . .
H17A H 0.365848 0.237921 -0.156353 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3056(3) 0.4172(3) -0.0603(2) 0.0267(5) Uani 1 1 d . . . . .
H18A H 0.345240 0.477201 -0.109153 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2337(3) 0.4690(3) 0.0420(2) 0.0242(5) Uani 1 1 d . . . . .
C20 C 0.2459(4) 0.7206(3) 0.0362(3) 0.0328(6) Uani 1 1 d . . . . .
H20A H 0.213640 0.803659 0.085738 0.049 Uiso 1 1 calc R U . . .
H20B H 0.365573 0.765352 0.036287 0.049 Uiso 1 1 calc R U . . .
H20C H 0.186003 0.672743 -0.048652 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0734(3) 0.7267(3) 0.2573(3) 0.0336(6) Uani 1 1 d . . . . .
H21A H 0.106449 0.805030 0.220300 0.050 Uiso 1 1 calc R U . . .
H21B H -0.047330 0.682453 0.252193 0.050 Uiso 1 1 calc R U . . .
H21C H 0.127050 0.776263 0.343977 0.050 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'
Cl Cl 0.3639 0.7018 '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 108.7(2) . . ?
C8 N1 C9 125.1(2) . . ?
C1 N1 C9 126.1(2) . . ?
C19 N2 C12 108.4(2) . . ?
C19 N2 C20 124.8(2) . . ?
C12 N2 C20 126.7(2) . . ?
C2 C1 N1 109.6(2) . . ?
C2 C1 C10 130.1(3) . . ?
N1 C1 C10 120.3(2) . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 C11 128.2(2) . . ?
C3 C2 C11 124.8(2) . . ?
C4 C3 C8 119.3(2) . . ?
C4 C3 C2 133.6(2) . . ?
C8 C3 C2 107.0(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4A 121.0 . . ?
C3 C4 H4A 121.0 . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 Cl1 118.4(2) . . ?
C6 C5 Cl1 118.7(2) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 H7A 120.9 . . ?
C8 C7 H7A 120.9 . . ?
N1 C8 C7 130.6(2) . . ?
N1 C8 C3 107.7(2) . . ?
C7 C8 C3 121.6(3) . . ?
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 114.6(2) . . ?
C13 C11 H11A 108.6 . . ?
C2 C11 H11A 108.6 . . ?
C13 C11 H11B 108.6 . . ?
C2 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 N2 110.0(2) . . ?
C13 C12 C21 129.3(2) . . ?
N2 C12 C21 120.7(2) . . ?
C12 C13 C14 106.5(2) . . ?
C12 C13 C11 127.9(2) . . ?
C14 C13 C11 125.6(2) . . ?
C15 C14 C19 119.1(2) . . ?
C15 C14 C13 133.7(2) . . ?
C19 C14 C13 107.2(2) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15A 121.2 . . ?
C14 C15 H15A 121.2 . . ?
C15 C16 C17 123.2(2) . . ?
C15 C16 Cl2 119.0(2) . . ?
C17 C16 Cl2 117.83(19) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C17 C18 C19 117.8(2) . . ?
C17 C18 H18A 121.1 . . ?
C19 C18 H18A 121.1 . . ?
N2 C19 C18 129.9(2) . . ?
N2 C19 C14 107.8(2) . . ?
C18 C19 C14 122.2(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
Cl1 C5 1.754(3) . ?
Cl2 C16 1.749(3) . ?
N1 C8 1.370(4) . ?
N1 C1 1.396(4) . ?
N1 C9 1.453(3) . ?
N2 C19 1.375(3) . ?
N2 C12 1.389(3) . ?
N2 C20 1.457(3) . ?
C1 C2 1.368(4) . ?
C1 C10 1.493(4) . ?
C2 C3 1.433(4) . ?
C2 C11 1.506(4) . ?
C3 C4 1.396(4) . ?
C3 C8 1.421(4) . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(4) . ?
C6 C7 1.380(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.398(4) . ?
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 1.503(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.374(4) . ?
C12 C21 1.498(4) . ?
C13 C14 1.431(3) . ?
C14 C15 1.407(3) . ?
C14 C19 1.417(3) . ?
C15 C16 1.377(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.402(4) . ?
C17 C18 1.380(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.399(4) . ?
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 1.1(3) . . . . ?
C9 N1 C1 C2 -176.9(2) . . . . ?
C8 N1 C1 C10 -178.9(2) . . . . ?
C9 N1 C1 C10 3.0(4) . . . . ?
N1 C1 C2 C3 -1.2(3) . . . . ?
C10 C1 C2 C3 178.8(3) . . . . ?
N1 C1 C2 C11 -178.8(2) . . . . ?
C10 C1 C2 C11 1.3(5) . . . . ?
C1 C2 C3 C4 -176.2(3) . . . . ?
C11 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C8 0.8(3) . . . . ?
C11 C2 C3 C8 178.5(2) . . . . ?
C8 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 C5 176.4(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 Cl1 179.25(18) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
Cl1 C5 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C1 N1 C8 C7 176.4(3) . . . . ?
C9 N1 C8 C7 -5.5(4) . . . . ?
C1 N1 C8 C3 -0.6(3) . . . . ?
C9 N1 C8 C3 177.5(2) . . . . ?
C6 C7 C8 N1 -176.3(3) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C4 C3 C8 N1 177.3(2) . . . . ?
C2 C3 C8 N1 -0.2(3) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C2 C3 C8 C7 -177.5(2) . . . . ?
C1 C2 C11 C13 -113.6(3) . . . . ?
C3 C2 C11 C13 69.2(3) . . . . ?
C19 N2 C12 C13 0.9(3) . . . . ?
C20 N2 C12 C13 178.4(2) . . . . ?
C19 N2 C12 C21 -178.2(2) . . . . ?
C20 N2 C12 C21 -0.8(4) . . . . ?
N2 C12 C13 C14 -0.7(3) . . . . ?
C21 C12 C13 C14 178.4(2) . . . . ?
N2 C12 C13 C11 -178.3(2) . . . . ?
C21 C12 C13 C11 0.8(4) . . . . ?
C2 C11 C13 C12 -110.6(3) . . . . ?
C2 C11 C13 C14 72.3(3) . . . . ?
C12 C13 C14 C15 -178.2(3) . . . . ?
C11 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C19 0.1(3) . . . . ?
C11 C13 C14 C19 177.8(2) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 C16 178.5(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 Cl2 179.13(18) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
Cl2 C16 C17 C18 -179.45(19) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C12 N2 C19 C18 178.0(2) . . . . ?
C20 N2 C19 C18 0.5(4) . . . . ?
C12 N2 C19 C14 -0.8(3) . . . . ?
C20 N2 C19 C14 -178.3(2) . . . . ?
C17 C18 C19 N2 -179.1(2) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C15 C14 C19 N2 179.0(2) . . . . ?
C13 C14 C19 N2 0.4(3) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
C13 C14 C19 C18 -178.5(2) . . . . ?
