#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:29:16 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158011.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_7158011
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 <i>tert</i>-butyl ether as a new methylene precursor.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; 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         'C23 H26 N2'
_chemical_formula_sum            'C23 H26 N2'
_chemical_formula_weight         330.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1551(3)
_cell_length_b                   9.5932(3)
_cell_length_c                   13.3690(6)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.7870
_cell_measurement_theta_min      5.5630
_cell_volume                     1815.41(11)
_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      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       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5174
_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         69.987
_diffrn_reflns_theta_min         5.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37152
_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    1.209
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0595
_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/[\s^2^(Fo^2^)+(0.1106P)^2^+0.9698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1462
_reflns_number_total             1713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00120e2.cif
_cod_data_source_block           Compound3e
_cod_depositor_comments
'Adding full bibliography for 7158011--7158015.cif.'
_cod_database_code               7158011
_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   0.900
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_file
; 
TITL full.res in Pbcn 
    full.res 
    created by SHELXL-2018/3 at 17:27:22 on 18-Nov-2020 
CELL 1.54184 14.1551 9.5932 13.369 90 90 90 
ZERR 4 0.0003 0.0003 0.0006 0 0 0 
LATT 1 
SYMM 0.5-X,0.5-Y,0.5+Z 
SYMM -X,+Y,0.5-Z 
SYMM 0.5+X,0.5-Y,-Z 
SFAC C H N 
UNIT 92 104 8 
TEMP -123 
SIZE 0.20 0.20 0.05 
  
OMIT 0 140 
L.S. 6 
PLAN 3 
CONF 
BOND $H 
fmap 2 
MORE -1 
ACTA 
  
REM EXTI    0.001671 
WGHT    0.110600    0.969800 
FVAR       4.95948 
N1    3    0.454843    0.330554    0.495055    11.00000    0.02869    0.02973 = 
         0.02718    0.00371   -0.00077    0.00188 
C1    1    0.504408    0.238427    0.434747    11.00000    0.02618    0.02661 = 
         0.03283    0.00601    0.00159   -0.00013 
C2    1    0.469264    0.242718    0.339254    11.00000    0.02550    0.02503 = 
         0.03135    0.00336    0.00077   -0.00140 
C3    1    0.393379    0.342289    0.339895    11.00000    0.02329    0.02462 = 
         0.03180    0.00434    0.00078   -0.00302 
C4    1    0.331006    0.392494    0.266731    11.00000    0.02906    0.03548 = 
         0.03498    0.00664   -0.00410   -0.00214 
AFIX  43 
H4A   2    0.334389    0.359403    0.199851    11.00000   -1.20000 
AFIX   0 
C5    1    0.264433    0.491195    0.293894    11.00000    0.02831    0.03909 = 
         0.04769    0.01192   -0.00647    0.00200 
AFIX  43 
H5A   2    0.222374    0.526482    0.244646    11.00000   -1.20000 
AFIX   0 
C6    1    0.257686    0.540040    0.391942    11.00000    0.02895    0.03203 = 
         0.05348    0.00676    0.00441    0.00475 
AFIX  43 
H6A   2    0.211298    0.607948    0.408147    11.00000   -1.20000 
AFIX   0 
C7    1    0.317447    0.491194    0.465940    11.00000    0.03081    0.02850 = 
         0.03949    0.00221    0.00621    0.00065 
AFIX  43 
H7A   2    0.312256    0.523043    0.533000    11.00000   -1.20000 
AFIX   0 
C8    1    0.385571    0.393491    0.438437    11.00000    0.02439    0.02687 = 
         0.03157    0.00628    0.00106   -0.00180 
C9    1    0.460994    0.341083    0.603852    11.00000    0.03831    0.03655 = 
         0.02767    0.00113   -0.00100   -0.00265 
AFIX  23 
H9A   2    0.444877    0.437238    0.624632    11.00000   -1.20000 
H9B   2    0.526705    0.321987    0.625189    11.00000   -1.20000 
AFIX   0 
C10   1    0.395071    0.239661    0.655103    11.00000    0.05724    0.04585 = 
         0.03292    0.00446    0.00570   -0.01033 
AFIX  33 
H10A  2    0.401055    0.249595    0.727784    11.00000   -1.50000 
H10B  2    0.329828    0.259424    0.635090    11.00000   -1.50000 
H10C  2    0.411608    0.144240    0.635647    11.00000   -1.50000 
AFIX   0 
C11   1    0.584442    0.154583    0.476784    11.00000    0.03400    0.03331 = 
         0.04276    0.00475   -0.00501    0.00563 
AFIX  33 
H11A  2    0.591644    0.175560    0.548119    11.00000   -1.50000 
H11B  2    0.571076    0.055055    0.468258    11.00000   -1.50000 
H11C  2    0.642937    0.178308    0.441462    11.00000   -1.50000 
AFIX   0 
C12   1    0.500000    0.158060    0.250000    10.50000    0.03126    0.02571 = 
         0.03678    0.00000    0.00141    0.00000 
AFIX   3 
H12A  2    0.448590    0.098980    0.230090    11.00000   -1.20000 
  
AFIX   0 
HKLF 4 
  
  
  
  
REM  full.res in Pbcn 
REM wR2 = 0.1860, GooF = S = 1.098, Restrained GooF = 1.098 for all data 
REM R1 = 0.0595 for 1462 Fo > 4sig(Fo) and 0.0671 for all 1713 data 
REM 114 parameters refined using 0 restraints 
  
END 
  
WGHT      0.1106      0.9405 
  
REM Highest difference peak  0.546,  deepest hole -0.489,  1-sigma level  0.064 
Q1    1   0.6141  0.0954  0.4212  11.00000  0.05    0.55 
Q2    1   0.5582  0.0876  0.5341  11.00000  0.05    0.52 
Q3    1   0.6341  0.2207  0.5084  11.00000  0.05    0.49 
;
_shelx_res_checksum              6403
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.45484(11) 0.33055(17) 0.49505(12) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.50441(14) 0.23843(19) 0.43475(15) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.46926(13) 0.24272(19) 0.33925(14) 0.0273(5) Uani 1 1 d . . . . .
C3 C 0.39338(13) 0.34229(19) 0.33990(14) 0.0266(5) Uani 1 1 d . . . . .
C4 C 0.33101(14) 0.3925(2) 0.26673(16) 0.0332(5) Uani 1 1 d . . . . .
H4A H 0.334389 0.359403 0.199851 0.040 Uiso 1 1 calc R U . . .
C5 C 0.26443(15) 0.4912(2) 0.29389(17) 0.0384(6) Uani 1 1 d . . . . .
H5A H 0.222374 0.526482 0.244646 0.046 Uiso 1 1 calc R U . . .
C6 C 0.25769(15) 0.5400(2) 0.39194(17) 0.0382(5) Uani 1 1 d . . . . .
H6A H 0.211298 0.607948 0.408147 0.046 Uiso 1 1 calc R U . . .
C7 C 0.31745(14) 0.4912(2) 0.46594(16) 0.0329(5) Uani 1 1 d . . . . .
H7A H 0.312256 0.523043 0.533000 0.040 Uiso 1 1 calc R U . . .
C8 C 0.38557(13) 0.3935(2) 0.43844(14) 0.0276(5) Uani 1 1 d . . . . .
C9 C 0.46099(15) 0.3411(2) 0.60385(15) 0.0342(5) Uani 1 1 d . . . . .
H9A H 0.444877 0.437238 0.624632 0.041 Uiso 1 1 calc R U . . .
H9B H 0.526705 0.321987 0.625189 0.041 Uiso 1 1 calc R U . . .
C10 C 0.39507(19) 0.2397(3) 0.65510(16) 0.0453(6) Uani 1 1 d . . . . .
H10A H 0.401055 0.249595 0.727784 0.068 Uiso 1 1 calc R U . . .
H10B H 0.329828 0.259424 0.635090 0.068 Uiso 1 1 calc R U . . .
H10C H 0.411608 0.144240 0.635647 0.068 Uiso 1 1 calc R U . . .
C11 C 0.58444(15) 0.1546(2) 0.47678(17) 0.0367(5) Uani 1 1 d . . . . .
H11A H 0.591644 0.175560 0.548119 0.055 Uiso 1 1 calc R U . . .
H11B H 0.571076 0.055055 0.468258 0.055 Uiso 1 1 calc R U . . .
H11C H 0.642937 0.178308 0.441462 0.055 Uiso 1 1 calc R U . . .
C12 C 0.500000 0.1581(3) 0.250000 0.0313(6) Uani 1 2 d S T P . .
H12A H 0.448590 0.098980 0.230090 0.038 Uiso 1 1 d R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0287(9) 0.0297(9) 0.0272(9) 0.0037(6) -0.0008(6) 0.0019(6)
C1 0.0262(10) 0.0266(9) 0.0328(11) 0.0060(7) 0.0016(8) -0.0001(8)
C2 0.0255(9) 0.0250(9) 0.0314(11) 0.0034(7) 0.0008(7) -0.0014(7)
C3 0.0233(9) 0.0246(9) 0.0318(11) 0.0043(7) 0.0008(7) -0.0030(7)
C4 0.0291(10) 0.0355(11) 0.0350(11) 0.0066(8) -0.0041(8) -0.0021(8)
C5 0.0283(10) 0.0391(12) 0.0477(13) 0.0119(9) -0.0065(9) 0.0020(8)
C6 0.0290(10) 0.0320(11) 0.0535(13) 0.0068(10) 0.0044(9) 0.0048(8)
C7 0.0308(10) 0.0285(10) 0.0395(11) 0.0022(8) 0.0062(8) 0.0007(8)
C8 0.0244(9) 0.0269(10) 0.0316(10) 0.0063(7) 0.0011(7) -0.0018(7)
C9 0.0383(12) 0.0365(11) 0.0277(11) 0.0011(8) -0.0010(8) -0.0027(8)
C10 0.0572(16) 0.0459(14) 0.0329(12) 0.0045(9) 0.0057(10) -0.0103(11)
C11 0.0340(11) 0.0333(11) 0.0428(12) 0.0048(9) -0.0050(9) 0.0056(8)
C12 0.0313(14) 0.0257(13) 0.0368(16) 0.000 0.0014(11) 0.000
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'
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 108.65(16) . . ?
C8 N1 C9 123.99(17) . . ?
C1 N1 C9 126.36(16) . . ?
C2 C1 N1 109.80(17) . . ?
C2 C1 C11 129.77(19) . . ?
N1 C1 C11 120.42(18) . . ?
C1 C2 C3 106.59(17) . . ?
C1 C2 C12 128.04(17) . . ?
C3 C2 C12 125.34(16) . . ?
C4 C3 C8 118.84(18) . . ?
C4 C3 C2 133.97(19) . . ?
C8 C3 C2 107.19(16) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 121.51(19) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 117.5(2) . . ?
C6 C7 H7A 121.2 . . ?
C8 C7 H7A 121.2 . . ?
N1 C8 C7 129.93(19) . . ?
N1 C8 C3 107.74(17) . . ?
C7 C8 C3 122.33(18) . . ?
N1 C9 C10 111.71(18) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 C2 114.8(2) . 3_655 ?
C2 C12 H12A 108.6 . . ?
C2 C12 H12A 108.5 3_655 . ?
C2 C12 H12A 108.50(9) . 3_655 ?
C2 C12 H12A 108.59(8) 3_655 3_655 ?
H12A C12 H12A 107.6 . 3_655 ?
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
N1 C8 1.378(2) . ?
N1 C1 1.387(3) . ?
N1 C9 1.461(3) . ?
C1 C2 1.371(3) . ?
C1 C11 1.499(3) . ?
C2 C3 1.437(3) . ?
C2 C12 1.508(2) . ?
C3 C4 1.403(3) . ?
C3 C8 1.410(3) . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.395(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9500 . ?
C9 C10 1.512(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12A 0.9600 3_655 ?
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(2) . . . . ?
C9 N1 C1 C2 170.00(18) . . . . ?
C8 N1 C1 C11 -179.93(17) . . . . ?
C9 N1 C1 C11 -11.0(3) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
C11 C1 C2 C3 -179.12(19) . . . . ?
N1 C1 C2 C12 -178.44(17) . . . . ?
C11 C1 C2 C12 2.7(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C12 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C3 C8 -0.6(2) . . . . ?
C12 C2 C3 C8 177.61(17) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 179.98(19) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C1 N1 C8 C7 178.86(19) . . . . ?
C9 N1 C8 C7 9.6(3) . . . . ?
C1 N1 C8 C3 -1.5(2) . . . . ?
C9 N1 C8 C3 -170.68(17) . . . . ?
C6 C7 C8 N1 178.22(19) . . . . ?
C6 C7 C8 C3 -1.4(3) . . . . ?
C4 C3 C8 N1 -179.05(16) . . . . ?
C2 C3 C8 N1 1.3(2) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C2 C3 C8 C7 -179.02(17) . . . . ?
C8 N1 C9 C10 81.4(2) . . . . ?
C1 N1 C9 C10 -85.9(2) . . . . ?
C1 C2 C12 C2 -123.1(2) . . . 3_655 ?
C3 C2 C12 C2 59.10(16) . . . 3_655 ?