#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:12:52 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128524.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_7128524
loop_
_publ_author_name
'Chen, Xinyu'
'Yang, Na'
'Zeng, Wen'
'Wang, Lei'
'Li, Pinhua'
'Li, Hongji'
_publ_section_title
;
 Metal-free dearomative [5+2]/[2+2] cycloaddition of 1H-indoles
 with ortho-(trimethylsilyl)aryl triflates.
;
_journal_issue                   57
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7047
_journal_page_last               7050
_journal_paper_doi               10.1039/d1cc02550c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C20 H15 N'
_chemical_formula_sum            'C20 H15 N'
_chemical_formula_weight         269.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.566(2)
_cell_length_b                   5.4612(7)
_cell_length_c                   14.391(2)
_cell_measurement_reflns_used    1605
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.61
_cell_volume                     1459.1(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6897
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.583
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0705 before and 0.0328 after correction.
The Ratio of minimum to maximum transmission is 0.8423.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0503
_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)+(0.0366P)²+0.0253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1786
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02550c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7128523--7128524.cif.'
_cod_database_code               7128524
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 N1, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N1, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C0AA(H0AA)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
C2 C 0.8760(2) 0.3860(8) 0.5199(3) 0.0649(11) Uani 1 1 d . . . . .
H2 H 0.8836 0.2533 0.4806 0.078 Uiso 1 1 calc R . . . .
C3 C 0.8115(2) 0.5073(8) 0.5187(3) 0.0700(13) Uani 1 1 d . . . . .
H3 H 0.7752 0.4561 0.4786 0.084 Uiso 1 1 calc R . . . .
C4 C 0.8001(2) 0.7033(8) 0.5760(3) 0.0649(12) Uani 1 1 d . . . . .
H4 H 0.7568 0.7885 0.5735 0.078 Uiso 1 1 calc R . . . .
C5 C 0.85305(19) 0.7740(7) 0.6373(3) 0.0530(11) Uani 1 1 d . . . . .
H5 H 0.8445 0.9036 0.6777 0.064 Uiso 1 1 calc R . . . .
C6 C 0.91872(19) 0.6550(7) 0.6397(2) 0.0416(9) Uani 1 1 d . . . . .
C7 C 0.97688(16) 0.7350(6) 0.7043(2) 0.0394(8) Uani 1 1 d . U . . .
C8 C 0.95580(17) 0.7976(6) 0.8010(2) 0.0399(9) Uani 1 1 d . . . . .
C9 C 0.90692(17) 0.6475(7) 0.8475(2) 0.0477(10) Uani 1 1 d . . . . .
H9 H 0.8872 0.5133 0.8169 0.057 Uiso 1 1 calc R . . . .
C10 C 0.8873(2) 0.6952(8) 0.9381(3) 0.0599(11) Uani 1 1 d . . . . .
H10 H 0.8555 0.5917 0.9690 0.072 Uiso 1 1 calc R . . . .
C11 C 0.9150(2) 0.8953(9) 0.9822(3) 0.0654(12) Uani 1 1 d . . . . .
H11 H 0.9010 0.9298 1.0429 0.078 Uiso 1 1 calc R . . . .
C12 C 0.9631(2) 1.0461(7) 0.9386(3) 0.0595(11) Uani 1 1 d . . . . .
H12 H 0.9816 1.1811 0.9699 0.071 Uiso 1 1 calc R . . . .
C13 C 0.98480(18) 0.9989(6) 0.8472(2) 0.0472(9) Uani 1 1 d . . . . .
C14 C 1.0401(2) 1.1522(6) 0.7986(3) 0.0597(11) Uani 1 1 d . . . . .
H14A H 1.0520 1.2937 0.8364 0.072 Uiso 1 1 calc R . . . .
H14B H 1.0211 1.2098 0.7398 0.072 Uiso 1 1 calc R . . . .
C15 C 1.1068(2) 1.0013(7) 0.7821(3) 0.0480(10) Uani 1 1 d . . . . .
C16 C 1.1719(2) 1.0537(7) 0.8247(3) 0.0613(11) Uani 1 1 d . . . . .
H16 H 1.1751 1.1886 0.8640 0.074 Uiso 1 1 calc R . . . .
C17 C 1.2319(2) 0.9110(9) 0.8104(3) 0.0679(12) Uani 1 1 d . . . . .
H17 H 1.2749 0.9488 0.8404 0.082 Uiso 1 1 calc R . . . .
C18 C 1.2285(2) 0.7134(8) 0.7520(3) 0.0668(12) Uani 1 1 d . . . . .
H18 H 1.2690 0.6165 0.7424 0.080 Uiso 1 1 calc R . . . .
C19 C 1.16481(19) 0.6590(7) 0.7078(3) 0.0564(11) Uani 1 1 d . . . . .
H19 H 1.1630 0.5275 0.6668 0.068 Uiso 1 1 calc R . . . .
C20 C 1.10312(18) 0.7974(6) 0.7233(2) 0.0420(8) Uani 1 1 d . U . . .
C0AA C 0.9298(2) 0.4612(7) 0.5795(3) 0.0533(10) Uani 1 1 d . . . . .
H0AA H 0.9740 0.3808 0.5792 0.064 Uiso 1 1 calc R . . . .
N1 N 1.04145(14) 0.7313(5) 0.67185(19) 0.0430(7) Uani 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
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
C3 C2 H2 120.1 . . ?
C3 C2 C0AA 119.8(4) . . ?
C0AA C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 C0AA 118.4(3) . . ?
C0AA C6 C7 120.5(3) . . ?
C8 C7 C6 117.4(3) . . ?
N1 C7 C6 116.4(3) . . ?
N1 C7 C8 126.1(3) . . ?
C9 C8 C7 119.0(3) . . ?
C13 C8 C7 121.8(3) . . ?
C13 C8 C9 119.2(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 118.9(3) . . ?
C8 C13 C14 118.9(3) . . ?
C12 C13 C14 122.2(3) . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C13 C14 C15 109.4(3) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C16 C15 C14 122.2(4) . . ?
C16 C15 C20 118.4(4) . . ?
C20 C15 C14 119.4(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.5(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(4) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 N1 124.1(3) . . ?
C19 C20 C15 119.3(3) . . ?
C19 C20 N1 116.5(3) . . ?
C2 C0AA C6 120.6(3) . . ?
C2 C0AA H0AA 119.7 . . ?
C6 C0AA H0AA 119.7 . . ?
C7 N1 C20 124.2(3) . . ?
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
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C2 C0AA 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(5) . ?
C6 C7 1.490(5) . ?
C6 C0AA 1.384(5) . ?
C7 C8 1.486(5) . ?
C7 N1 1.287(4) . ?
C8 C9 1.394(4) . ?
C8 C13 1.392(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(5) . ?
C13 C14 1.499(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.506(5) . ?
C15 C16 1.385(5) . ?
C15 C20 1.400(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(5) . ?
C20 N1 1.410(4) . ?
C0AA H0AA 0.9300 . ?
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
C2 C3 C4 C5 -2.1(6) . . . . ?
C3 C2 C0AA C6 1.4(6) . . . . ?
C3 C4 C5 C6 2.3(6) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C4 C5 C6 C0AA -0.6(5) . . . . ?
C5 C6 C7 C8 43.0(4) . . . . ?
C5 C6 C7 N1 -140.4(3) . . . . ?
C5 C6 C0AA C2 -1.2(6) . . . . ?
C6 C7 C8 C9 42.8(4) . . . . ?
C6 C7 C8 C13 -138.7(3) . . . . ?
C6 C7 N1 C20 -179.1(3) . . . . ?
C7 C6 C0AA C2 179.8(3) . . . . ?
C7 C8 C9 C10 178.3(3) . . . . ?
C7 C8 C13 C12 -179.4(3) . . . . ?
C7 C8 C13 C14 -1.6(5) . . . . ?
C8 C7 N1 C20 -2.8(5) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C8 C13 C14 C15 -64.9(4) . . . . ?
C9 C8 C13 C12 -0.9(5) . . . . ?
C9 C8 C13 C14 176.9(3) . . . . ?
C9 C10 C11 C12 -1.5(6) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C8 0.9(5) . . . . ?
C11 C12 C13 C14 -176.9(3) . . . . ?
C12 C13 C14 C15 112.8(4) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
C13 C14 C15 C16 -114.4(4) . . . . ?
C13 C14 C15 C20 64.1(4) . . . . ?
C14 C15 C16 C17 178.6(4) . . . . ?
C14 C15 C20 C19 179.7(3) . . . . ?
C14 C15 C20 N1 4.9(5) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C15 C20 N1 C7 -43.0(5) . . . . ?
C16 C15 C20 C19 -1.7(5) . . . . ?
C16 C15 C20 N1 -176.5(3) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C17 C18 C19 C20 -1.8(6) . . . . ?
C18 C19 C20 C15 2.6(6) . . . . ?
C18 C19 C20 N1 177.8(3) . . . . ?
C19 C20 N1 C7 142.1(3) . . . . ?
C20 C15 C16 C17 0.0(5) . . . . ?
C0AA C2 C3 C4 0.3(6) . . . . ?
C0AA C6 C7 C8 -138.0(3) . . . . ?
C0AA C6 C7 N1 38.6(5) . . . . ?
N1 C7 C8 C9 -133.4(3) . . . . ?
N1 C7 C8 C13 45.1(5) . . . . ?
