#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:30:03 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158113.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_7158113
loop_
_publ_author_name
'Zhang, Wei'
'Xiang, Shiqun'
'Fan, Weibin'
'Jin, Jiang'
'Li, Yinghua'
'Huang, Deguang'
_publ_section_title
;
 A three-component iodine-catalyzed oxidative coupling reaction: a
 heterodifunctionalization of 3-methylindoles.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5794
_journal_page_last               5799
_journal_paper_doi               10.1039/d1ob00730k
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H24 N2 O4'
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.40
_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
;
2021-03-04 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                101.921(6)
_cell_angle_beta                 111.131(7)
_cell_angle_gamma                105.454(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9866(6)
_cell_length_b                   10.4170(6)
_cell_length_c                   10.4938(8)
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.5240
_cell_measurement_theta_min      4.6390
_cell_volume                     924.18(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.966
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_min         4.677
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82699
_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    1.238
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0805P)²+1.0122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2924
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00730k2.cif
_cod_data_source_block           Compound3o
_cod_depositor_comments
'Adding full bibliography for 7158113--7158115.cif.'
_cod_original_cell_volume        924.17(12)
_cod_database_code               7158113
_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   0.815
_shelx_estimated_absorpt_t_max   0.901
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
O1 O 0.6410(2) 0.55889(18) 0.83643(18) 0.0345(4) Uani 1 1 d . U . . .
O2 O 0.7230(2) 0.77526(18) 0.81940(19) 0.0362(4) Uani 1 1 d . U . . .
O3 O 0.18232(17) 0.71169(16) 0.60361(17) 0.0259(3) Uani 1 1 d . U . . .
O4 O 0.29051(19) 0.85789(17) 0.70022(18) 0.0306(3) Uani 1 1 d . U . . .
C1 C 0.2504(3) 0.7650(2) 0.4105(2) 0.0248(3) Uani 1 1 d . U . . .
C2 C 0.1394(3) 0.8018(2) 0.3185(2) 0.0279(4) Uani 1 1 d . U . . .
H2A H 0.036760 0.772333 0.309368 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1826(3) 0.8834(2) 0.2396(3) 0.0307(4) Uani 1 1 d . U . . .
H3A H 0.108643 0.910607 0.176225 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3327(3) 0.9254(2) 0.2529(3) 0.0308(4) Uani 1 1 d . U . . .
H4A H 0.360159 0.982478 0.199570 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4436(3) 0.8857(2) 0.3426(2) 0.0283(4) Uani 1 1 d . U . . .
H5A H 0.545919 0.913190 0.350890 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3979(3) 0.8044(2) 0.4189(2) 0.0249(3) Uani 1 1 d . U . . .
C7 C 0.2381(3) 0.6716(2) 0.5012(2) 0.0239(3) Uani 1 1 d . U . . .
C8 C 0.1244(3) 0.5212(2) 0.4041(2) 0.0269(4) Uani 1 1 d . U . . .
H8A H 0.155785 0.485981 0.329784 0.040 Uiso 1 1 calc R U . . .
H8B H 0.124449 0.459570 0.463145 0.040 Uiso 1 1 calc R U . . .
H8C H 0.020195 0.521743 0.357235 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2071(3) 0.9187(3) 0.7654(3) 0.0328(4) Uani 1 1 d . U . . .
C10 C 0.0754(4) 0.9329(4) 0.6464(4) 0.0543(7) Uani 1 1 d . U . . .
H10A H 0.017015 0.974138 0.688496 0.082 Uiso 1 1 calc R U . . .
H10B H 0.117558 0.994307 0.599791 0.082 Uiso 1 1 calc R U . . .
H10C H 0.006506 0.839248 0.574053 0.082 Uiso 1 1 calc R U . . .
C11 C 0.3274(3) 1.0638(3) 0.8676(3) 0.0408(5) Uani 1 1 d . U . . .
H11A H 0.281331 1.114583 0.918009 0.061 Uiso 1 1 calc R U . . .
H11B H 0.415488 1.052916 0.938803 0.061 Uiso 1 1 calc R U . . .
H11C H 0.362781 1.117507 0.811737 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1528(4) 0.8339(3) 0.8486(3) 0.0519(6) Uani 1 1 d . U . . .
H12A H 0.096719 0.877969 0.891486 0.078 Uiso 1 1 calc R U . . .
H12B H 0.084017 0.737520 0.783025 0.078 Uiso 1 1 calc R U . . .
H12C H 0.242302 0.830803 0.925868 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4062(3) 0.6801(2) 0.5752(2) 0.0240(3) Uani 1 1 d . U . . .
C14 C 0.4574(3) 0.6222(2) 0.6812(2) 0.0264(3) Uani 1 1 d . U . . .
C15 C 0.3459(3) 0.5240(2) 0.7069(3) 0.0279(4) Uani 1 1 d . U . . .
C16 C 0.6208(3) 0.6628(2) 0.7835(3) 0.0290(4) Uani 1 1 d . U . . .
C17 C 0.7908(3) 0.5936(3) 0.9564(3) 0.0369(5) Uani 1 1 d . U . . .
H17A H 0.801583 0.659326 1.045579 0.044 Uiso 1 1 calc R U . . .
H17B H 0.875436 0.639241 0.933221 0.044 Uiso 1 1 calc R U . . .
C18 C 0.7976(3) 0.4574(3) 0.9776(3) 0.0395(6) Uani 1 1 d . U . . .
H18A H 0.897129 0.476011 1.057791 0.059 Uiso 1 1 calc R U . . .
H18B H 0.713286 0.413435 1.000375 0.059 Uiso 1 1 calc R U . . .
H18C H 0.786793 0.393445 0.888543 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6357(3) 0.7487(3) 0.5227(3) 0.0306(5) Uani 1 1 d . U . . .
H19A H 0.668787 0.808034 0.470005 0.046 Uiso 1 1 calc R U . . .
H19B H 0.713212 0.785979 0.624294 0.046 Uiso 1 1 calc R U . . .
H19C H 0.624880 0.651667 0.478508 0.046 Uiso 1 1 calc R U . . .
N1 N 0.2596(3) 0.4421(2) 0.7253(2) 0.0373(5) Uani 1 1 d . U . . .
N2 N 0.4874(2) 0.74940(19) 0.5156(2) 0.0246(3) 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 0.0181 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'
O O 0.0492 0.0322 '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
C16 O1 C17 116.44(19) . . ?
C7 O3 O4 106.22(14) . . ?
C9 O4 O3 106.39(15) . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 C7 108.66(19) . . ?
C2 C1 C7 130.7(2) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 H5A 121.6 . . ?
C4 C5 H5A 121.6 . . ?
C5 C6 C1 122.7(2) . . ?
C5 C6 N2 127.8(2) . . ?
C1 C6 N2 109.46(19) . . ?
O3 C7 C1 115.74(18) . . ?
O3 C7 C8 104.73(17) . . ?
C1 C7 C8 110.21(18) . . ?
O3 C7 C13 111.94(17) . . ?
C1 C7 C13 101.96(17) . . ?
C8 C7 C13 112.52(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C12 111.5(2) . . ?
O4 C9 C10 108.1(2) . . ?
C12 C9 C10 112.8(3) . . ?
O4 C9 C11 103.07(19) . . ?
C12 C9 C11 110.4(2) . . ?
C10 C9 C11 110.5(2) . . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 127.9(2) . . ?
N2 C13 C7 108.07(18) . . ?
C14 C13 C7 124.0(2) . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 C16 124.9(2) . . ?
C15 C14 C16 115.4(2) . . ?
N1 C15 C14 177.3(3) . . ?
O2 C16 O1 123.8(2) . . ?
O2 C16 C14 125.4(2) . . ?
O1 C16 C14 110.8(2) . . ?
O1 C17 C18 106.8(2) . . ?
O1 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O1 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 N2 C6 111.23(18) . . ?
C13 N2 C19 126.5(2) . . ?
C6 N2 C19 121.31(19) . . ?
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
O1 C16 1.344(3) . ?
O1 C17 1.456(3) . ?
O2 C16 1.208(3) . ?
O3 C7 1.418(3) . ?
O3 O4 1.487(2) . ?
O4 C9 1.441(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.506(3) . ?
C2 C3 1.396(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5A 0.9500 . ?
C6 N2 1.420(3) . ?
C7 C8 1.530(3) . ?
C7 C13 1.543(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C12 1.497(4) . ?
C9 C10 1.519(4) . ?
C9 C11 1.520(3) . ?
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 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.345(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.442(3) . ?
C14 C16 1.475(3) . ?
C15 N1 1.143(3) . ?
C17 C18 1.497(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N2 1.458(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C7 O3 O4 C9 158.41(17) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
C7 C1 C2 C3 -175.5(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 N2 179.3(2) . . . . ?
C2 C1 C6 C5 2.7(3) . . . . ?
C7 C1 C6 C5 177.3(2) . . . . ?
C2 C1 C6 N2 -177.64(19) . . . . ?
C7 C1 C6 N2 -3.1(2) . . . . ?
O4 O3 C7 C1 -58.5(2) . . . . ?
O4 O3 C7 C8 179.95(15) . . . . ?
O4 O3 C7 C13 57.8(2) . . . . ?
C6 C1 C7 O3 128.3(2) . . . . ?
C2 C1 C7 O3 -57.9(3) . . . . ?
C6 C1 C7 C8 -113.2(2) . . . . ?
C2 C1 C7 C8 60.6(3) . . . . ?
C6 C1 C7 C13 6.5(2) . . . . ?
C2 C1 C7 C13 -179.7(2) . . . . ?
O3 O4 C9 C12 58.7(3) . . . . ?
O3 O4 C9 C10 -65.9(2) . . . . ?
O3 O4 C9 C11 177.13(18) . . . . ?
O3 C7 C13 N2 -132.27(19) . . . . ?
C1 C7 C13 N2 -7.9(2) . . . . ?
C8 C7 C13 N2 110.1(2) . . . . ?
O3 C7 C13 C14 49.1(3) . . . . ?
C1 C7 C13 C14 173.4(2) . . . . ?
C8 C7 C13 C14 -68.5(3) . . . . ?
N2 C13 C14 C15 -165.4(2) . . . . ?
C7 C13 C14 C15 12.9(3) . . . . ?
N2 C13 C14 C16 20.9(4) . . . . ?
C7 C13 C14 C16 -160.7(2) . . . . ?
C17 O1 C16 O2 7.8(4) . . . . ?
C17 O1 C16 C14 -170.1(2) . . . . ?
C13 C14 C16 O2 24.2(4) . . . . ?
C15 C14 C16 O2 -149.7(2) . . . . ?
C13 C14 C16 O1 -157.9(2) . . . . ?
C15 C14 C16 O1 28.2(3) . . . . ?
C16 O1 C17 C18 -169.4(2) . . . . ?
C14 C13 N2 C6 -174.8(2) . . . . ?
C7 C13 N2 C6 6.7(2) . . . . ?
C14 C13 N2 C19 16.5(4) . . . . ?
C7 C13 N2 C19 -162.1(2) . . . . ?
C5 C6 N2 C13 177.2(2) . . . . ?
C1 C6 N2 C13 -2.4(3) . . . . ?
C5 C6 N2 C19 -13.4(3) . . . . ?
C1 C6 N2 C19 167.0(2) . . . . ?
