#------------------------------------------------------------------------------
#$Date: 2022-03-02 03:39:21 +0200 (Wed, 02 Mar 2022) $
#$Revision: 273200 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158541.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_7158541
loop_
_publ_author_name
'Yi, Zi-Juan'
'Sun, Jian-Ting'
'Yang, Tian-Yu'
'Yu, Xian-Yong'
'Han, Xiao-Li'
'Wei, Bang-Guo'
_publ_section_title
;
 Cu(OTf)2-catalyzed C3 aza-Friedel--Crafts alkylation of indoles with
 N,O-acetals
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02383G
_journal_year                    2022
_chemical_formula_sum            'C21 H22 Cl2 N2 O3'
_chemical_formula_weight         421.30
_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-2013
_audit_update_record
;
2021-10-26 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                112.905(2)
_cell_angle_beta                 103.286(2)
_cell_angle_gamma                96.447(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2206(5)
_cell_length_b                   11.1857(6)
_cell_length_c                   11.8704(7)
_cell_measurement_reflns_used    8349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.185
_cell_measurement_theta_min      5.105
_cell_volume                     1069.43(11)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20962
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.127
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0509P)²+0.4443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02383g2.cif
_cod_data_source_block           mo_dd21019_0m
_cod_original_cell_volume        1069.43(10)
_cod_database_code               7158541
_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   0.950
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2013-4
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 0.10710(8) 0.66331(7) 1.03598(6) 0.0762(2) Uani 1 1 d . . . . .
Cl2 Cl 0.44882(7) 0.66289(7) 1.03745(6) 0.0757(2) Uani 1 1 d . . . . .
O1 O 0.65162(14) 0.33692(15) 0.51894(14) 0.0552(4) Uani 1 1 d . . . . .
N1 N -0.02845(16) 0.36988(17) 0.54948(15) 0.0465(4) Uani 1 1 d . . . . .
H1 H -0.1266 0.3555 0.5261 0.056 Uiso 1 1 calc R U . . .
N2 N 0.43445(16) 0.26983(17) 0.55384(15) 0.0440(4) Uani 1 1 d . . . . .
H2 H 0.3909 0.2274 0.5884 0.053 Uiso 1 1 calc R U . . .
C1 C 0.06543(19) 0.44366(19) 0.67140(18) 0.0401(4) Uani 1 1 d . . . . .
C2 C 0.0301(2) 0.5111(2) 0.78381(19) 0.0485(5) Uani 1 1 d . . . . .
H2A H -0.0707 0.5115 0.7839 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1489(2) 0.5771(2) 0.89450(19) 0.0489(5) Uani 1 1 d . . . . .
C4 C 0.3010(2) 0.5757(2) 0.89516(19) 0.0486(5) Uani 1 1 d . . . . .
C5 C 0.3361(2) 0.50903(19) 0.78384(18) 0.0442(4) Uani 1 1 d . . . . .
H5 H 0.4373 0.5091 0.7850 0.053 Uiso 1 1 calc R U . . .
C6 C 0.21733(18) 0.44113(17) 0.66887(17) 0.0364(4) Uani 1 1 d . . . . .
C7 C 0.21034(18) 0.36291(18) 0.53868(17) 0.0366(4) Uani 1 1 d . . . . .
C8 C 0.05925(19) 0.32234(19) 0.47029(18) 0.0427(4) Uani 1 1 d . . . . .
H8 H 0.0211 0.2699 0.3824 0.051 Uiso 1 1 calc R U . . .
C9 C 0.34487(18) 0.33659(18) 0.48867(17) 0.0368(4) Uani 1 1 d . . . . .
H9 H 0.4098 0.4230 0.5111 0.044 Uiso 1 1 calc R U . . .
C10 C 0.29781(19) 0.25956(18) 0.34415(17) 0.0396(4) Uani 1 1 d . . . . .
C11 C 0.2550(3) 0.1220(2) 0.2848(2) 0.0613(6) Uani 1 1 d . . . . .
H11 H 0.2586 0.0744 0.3340 0.074 Uiso 1 1 calc R U . . .
C12 C 0.2068(3) 0.0548(3) 0.1523(3) 0.0804(8) Uani 1 1 d . . . . .
H12 H 0.1779 -0.0377 0.1132 0.096 Uiso 1 1 calc R U . . .
C13 C 0.2015(3) 0.1235(3) 0.0787(2) 0.0783(8) Uani 1 1 d . . . . .
H13 H 0.1680 0.0779 -0.0102 0.094 Uiso 1 1 calc R U . . .
C14 C 0.2457(3) 0.2595(3) 0.1364(2) 0.0717(7) Uani 1 1 d . . . . .
H14 H 0.2434 0.3065 0.0865 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2936(2) 0.3273(2) 0.2685(2) 0.0530(5) Uani 1 1 d . . . . .
H15 H 0.3234 0.4198 0.3069 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5818(2) 0.2723(2) 0.56164(17) 0.0429(4) Uani 1 1 d . . . . .
C17 C 0.6552(3) 0.1911(3) 0.6233(2) 0.0647(6) Uani 1 1 d . . . . .
H17A H 0.6615 0.1092 0.5581 0.097 Uiso 1 1 calc R U . . .
H17B H 0.5949 0.1719 0.6728 0.097 Uiso 1 1 calc R U . . .
H17C H 0.7562 0.2402 0.6784 0.097 Uiso 1 1 calc R U . . .
O2 O 0.2982(3) 1.0898(2) 0.6442(2) 0.1047(8) Uani 1 1 d . . . . .
O3 O 0.22795(19) 0.99800(17) 0.76110(17) 0.0680(5) Uani 1 1 d . . . . .
C18 C 0.2125(3) 1.0725(2) 0.6990(2) 0.0619(6) Uani 1 1 d . . . . .
C19 C 0.0770(4) 1.1322(4) 0.7050(5) 0.1321(17) Uani 1 1 d . . . . .
H19A H -0.0059 1.0696 0.7017 0.198 Uiso 1 1 calc R U . . .
H19B H 0.0472 1.1539 0.6335 0.198 Uiso 1 1 calc R U . . .
H19C H 0.1020 1.2116 0.7834 0.198 Uiso 1 1 calc R U . . .
C20 C 0.3616(3) 0.9413(3) 0.7669(3) 0.0758(7) Uani 1 1 d . . . . .
H20A H 0.4528 1.0116 0.8188 0.091 Uiso 1 1 calc R U . . .
H20B H 0.3707 0.8966 0.6814 0.091 Uiso 1 1 calc R U . . .
C21 C 0.3481(4) 0.8465(3) 0.8224(3) 0.0956(10) Uani 1 1 d . . . . .
H21A H 0.2577 0.7772 0.7708 0.143 Uiso 1 1 calc R U . . .
H21B H 0.3415 0.8916 0.9077 0.143 Uiso 1 1 calc R U . . .
H21C H 0.4363 0.8083 0.8252 0.143 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C1 N1 C8 108.84(14) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C16 N2 C9 122.31(16) . . ?
C16 N2 H2 118.8 . . ?
C9 N2 H2 118.8 . . ?
N1 C1 C2 130.06(16) . . ?
N1 C1 C6 107.68(15) . . ?
C2 C1 C6 122.26(17) . . ?
C3 C2 C1 117.63(17) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 121.42(18) . . ?
C2 C3 Cl1 118.33(15) . . ?
C4 C3 Cl1 120.25(16) . . ?
C5 C4 C3 121.01(18) . . ?
C5 C4 Cl2 118.97(16) . . ?
C3 C4 Cl2 120.00(15) . . ?
C4 C5 C6 118.98(17) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.69(16) . . ?
C5 C6 C7 134.37(16) . . ?
C1 C6 C7 106.94(15) . . ?
C8 C7 C6 106.23(15) . . ?
C8 C7 C9 127.64(16) . . ?
C6 C7 C9 126.08(15) . . ?
C7 C8 N1 110.31(16) . . ?
C7 C8 H8 124.8 . . ?
N1 C8 H8 124.8 . . ?
N2 C9 C7 109.27(14) . . ?
N2 C9 C10 112.16(15) . . ?
C7 C9 C10 112.54(14) . . ?
N2 C9 H9 107.5 . . ?
C7 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C15 C10 C11 118.45(19) . . ?
C15 C10 C9 119.77(17) . . ?
C11 C10 C9 121.77(18) . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.8(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O1 C16 N2 121.39(18) . . ?
O1 C16 C17 122.56(17) . . ?
N2 C16 C17 116.04(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 O3 C20 117.46(19) . . ?
O2 C18 O3 122.8(2) . . ?
O2 C18 C19 123.8(2) . . ?
O3 C18 C19 113.3(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 109.6(2) . . ?
O3 C20 H20A 109.7 . . ?
C21 C20 H20A 109.7 . . ?
O3 C20 H20B 109.7 . . ?
C21 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 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 C3 1.737(2) . ?
Cl2 C4 1.739(2) . ?
O1 C16 1.234(2) . ?
N1 C1 1.363(2) . ?
N1 C8 1.370(2) . ?
N1 H1 0.8600 . ?
N2 C16 1.337(2) . ?
N2 C9 1.460(2) . ?
N2 H2 0.8600 . ?
C1 C2 1.388(3) . ?
C1 C6 1.411(2) . ?
C2 C3 1.368(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.403(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.431(2) . ?
C7 C8 1.363(2) . ?
C7 C9 1.504(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.516(2) . ?
C9 H9 0.9800 . ?
C10 C15 1.379(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.499(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O2 C18 1.177(3) . ?
O3 C18 1.309(3) . ?
O3 C20 1.448(3) . ?
C18 C19 1.484(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.458(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.01 2.8513(18) 165.5 1_455
N1 H1 O1 0.86 2.01 2.8513(18) 165.5 1_455
N2 H2 O2 0.86 2.07 2.919(2) 167.5 1_545
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 -179.9(2) . . . . ?
C8 N1 C1 C6 -0.6(2) . . . . ?
N1 C1 C2 C3 179.4(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 Cl1 179.48(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
Cl1 C3 C4 C5 -179.38(16) . . . . ?
C2 C3 C4 Cl2 179.03(16) . . . . ?
Cl1 C3 C4 Cl2 -1.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
Cl2 C4 C5 C6 -178.70(15) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -179.67(19) . . . . ?
N1 C1 C6 C5 -179.24(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C7 0.5(2) . . . . ?
C2 C1 C6 C7 179.82(17) . . . . ?
C5 C6 C7 C8 179.5(2) . . . . ?
C1 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C9 -2.7(3) . . . . ?
C1 C6 C7 C9 177.60(17) . . . . ?
C6 C7 C8 N1 -0.2(2) . . . . ?
C9 C7 C8 N1 -177.95(17) . . . . ?
C1 N1 C8 C7 0.5(2) . . . . ?
C16 N2 C9 C7 -157.74(17) . . . . ?
C16 N2 C9 C10 76.8(2) . . . . ?
C8 C7 C9 N2 -123.0(2) . . . . ?
C6 C7 C9 N2 59.6(2) . . . . ?
C8 C7 C9 C10 2.2(3) . . . . ?
C6 C7 C9 C10 -175.10(16) . . . . ?
N2 C9 C10 C15 -143.43(17) . . . . ?
C7 C9 C10 C15 92.9(2) . . . . ?
N2 C9 C10 C11 38.1(2) . . . . ?
C7 C9 C10 C11 -85.6(2) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C9 C10 C11 C12 177.4(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C9 C10 C15 C14 -177.59(19) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C9 N2 C16 O1 3.4(3) . . . . ?
C9 N2 C16 C17 -175.77(17) . . . . ?
C20 O3 C18 O2 3.4(4) . . . . ?
C20 O3 C18 C19 -176.7(3) . . . . ?
C18 O3 C20 C21 -171.6(2) . . . . ?
