#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:30:03 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158114.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_7158114
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         'C17 H20 N2 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-24 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.798(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7888(4)
_cell_length_b                   19.6193(8)
_cell_length_c                   10.0883(4)
_cell_measurement_reflns_used    2757
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.0580
_cell_measurement_theta_min      5.1520
_cell_volume                     1636.71(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)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.991
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         4.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88921
_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            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0440
_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)+(0.0705P)²+0.3799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             3082
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00730k2.cif
_cod_data_source_block           Compound3s
_cod_depositor_comments
'Adding full bibliography for 7158113--7158115.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158114
_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   0.761
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.91294(13) 0.17392(5) 0.38639(11) 0.0238(3) Uani 1 1 d . . . . .
O2 O 1.02012(14) 0.12436(6) 0.35021(11) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.61780(16) -0.05177(6) 0.41422(13) 0.0347(3) Uani 1 1 d . . . . .
O4 O 0.45768(15) -0.01195(6) 0.20300(12) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.86436(16) 0.03096(7) 0.56531(14) 0.0247(3) Uani 1 1 d . . . . .
H1A H 0.832844 -0.011269 0.570002 0.030 Uiso 1 1 calc R U . . .
N2 N 0.55937(19) 0.14758(8) 0.14142(16) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.9997(2) 0.06154(9) 0.66782(16) 0.0242(3) Uani 1 1 d . . . . .
C2 C 1.1077(2) 0.03310(9) 0.78916(17) 0.0280(4) Uani 1 1 d . . . . .
H2A H 1.098122 -0.012927 0.814510 0.034 Uiso 1 1 calc R U . . .
C3 C 1.2308(2) 0.07509(9) 0.87201(17) 0.0304(4) Uani 1 1 d . . . . .
H3A H 1.306944 0.057329 0.955948 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2450(2) 0.14256(10) 0.83487(18) 0.0315(4) Uani 1 1 d . . . . .
H4A H 1.330818 0.169947 0.893167 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1344(2) 0.17026(9) 0.71272(17) 0.0279(4) Uani 1 1 d . . . . .
H5A H 1.142750 0.216358 0.687173 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0123(2) 0.12861(8) 0.63011(16) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.8720(2) 0.14452(8) 0.49771(16) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.7556(2) 0.19607(9) 0.52499(18) 0.0295(4) Uani 1 1 d . . . . .
H8A H 0.720456 0.179617 0.601721 0.044 Uiso 1 1 calc R U . . .
H8B H 0.810427 0.240040 0.551345 0.044 Uiso 1 1 calc R U . . .
H8C H 0.661164 0.201612 0.439406 0.044 Uiso 1 1 calc R U . . .
C9 C 1.1049(2) 0.16285(9) 0.27382(16) 0.0263(4) Uani 1 1 d . . . . .
C10 C 1.2154(2) 0.21479(11) 0.3713(2) 0.0408(5) Uani 1 1 d . . . . .
H10A H 1.272419 0.240692 0.319520 0.061 Uiso 1 1 calc R U . . .
H10B H 1.150837 0.246003 0.406629 0.061 Uiso 1 1 calc R U . . .
H10C H 1.294194 0.191216 0.450795 0.061 Uiso 1 1 calc R U . . .
C11 C 1.2031(3) 0.10836(11) 0.2336(2) 0.0397(5) Uani 1 1 d . . . . .
H11A H 1.266248 0.129079 0.180564 0.060 Uiso 1 1 calc R U . . .
H11B H 1.276466 0.086852 0.319042 0.060 Uiso 1 1 calc R U . . .
H11C H 1.130225 0.073866 0.175109 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9830(2) 0.19529(11) 0.14438(19) 0.0396(5) Uani 1 1 d . . . . .
H12A H 1.040359 0.221252 0.092925 0.059 Uiso 1 1 calc R U . . .
H12B H 0.917843 0.159585 0.083167 0.059 Uiso 1 1 calc R U . . .
H12C H 0.912174 0.225956 0.173592 0.059 Uiso 1 1 calc R U . . .
C13 C 0.79009(19) 0.07428(8) 0.46022(16) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.65997(19) 0.05968(8) 0.34236(16) 0.0243(3) Uani 1 1 d . . . . .
C15 C 0.6045(2) 0.10877(9) 0.23175(17) 0.0268(4) Uani 1 1 d . . . . .
C16 C 0.5802(2) -0.00648(9) 0.32641(17) 0.0262(4) Uani 1 1 d . . . . .
C17 C 0.3690(2) -0.07520(10) 0.1786(2) 0.0395(5) Uani 1 1 d . . . . .
H17A H 0.283252 -0.073663 0.086302 0.059 Uiso 1 1 calc R U . . .
H17B H 0.442660 -0.113011 0.180617 0.059 Uiso 1 1 calc R U . . .
H17C H 0.320926 -0.081928 0.252184 0.059 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'
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
C7 O1 O2 106.37(10) . . ?
C9 O2 O1 105.81(11) . . ?
C16 O4 C17 116.32(14) . . ?
C13 N1 C1 111.80(13) . . ?
C13 N1 H1A 124.1 . . ?
C1 N1 H1A 124.1 . . ?
C6 C1 C2 122.04(15) . . ?
C6 C1 N1 109.07(13) . . ?
C2 C1 N1 128.88(16) . . ?
C1 C2 C3 116.90(16) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C2 C3 C4 121.59(16) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C5 120.55(16) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 117.96(16) . . ?
C6 C5 H5A 121.0 . . ?
C4 C5 H5A 121.0 . . ?
C5 C6 C1 120.96(15) . . ?
C5 C6 C7 130.18(15) . . ?
C1 C6 C7 108.79(14) . . ?
O1 C7 C6 115.82(13) . . ?
O1 C7 C8 103.83(12) . . ?
C6 C7 C8 111.89(13) . . ?
O1 C7 C13 113.17(12) . . ?
C6 C7 C13 101.86(13) . . ?
C8 C7 C13 110.49(13) . . ?
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 . . ?
O2 C9 C11 102.52(14) . . ?
O2 C9 C10 109.63(13) . . ?
C11 C9 C10 110.51(15) . . ?
O2 C9 C12 109.56(13) . . ?
C11 C9 C12 111.44(15) . . ?
C10 C9 C12 112.69(16) . . ?
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 . . ?
N1 C13 C14 126.27(15) . . ?
N1 C13 C7 108.07(13) . . ?
C14 C13 C7 125.61(14) . . ?
C13 C14 C15 119.99(15) . . ?
C13 C14 C16 120.66(15) . . ?
C15 C14 C16 119.32(14) . . ?
N2 C15 C14 179.08(18) . . ?
O3 C16 O4 123.30(16) . . ?
O3 C16 C14 124.54(15) . . ?
O4 C16 C14 112.15(14) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C7 1.4131(19) . ?
O1 O2 1.4829(15) . ?
O2 C9 1.4519(19) . ?
O3 C16 1.219(2) . ?
O4 C16 1.346(2) . ?
O4 C17 1.441(2) . ?
N1 C13 1.343(2) . ?
N1 C1 1.418(2) . ?
N1 H1A 0.8800 . ?
N2 C15 1.150(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.387(2) . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.512(2) . ?
C7 C8 1.529(2) . ?
C7 C13 1.541(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.513(3) . ?
C9 C10 1.517(2) . ?
C9 C12 1.520(2) . ?
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 C14 1.372(2) . ?
C14 C15 1.429(2) . ?
C14 C16 1.458(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 O1 O2 C9 -160.80(12) . . . . ?
C13 N1 C1 C6 1.66(19) . . . . ?
C13 N1 C1 C2 -178.64(16) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C2 C3 -179.89(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C4 C5 C6 C7 176.75(16) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 179.81(15) . . . . ?
C2 C1 C6 C7 -177.03(15) . . . . ?
N1 C1 C6 C7 2.69(18) . . . . ?
O2 O1 C7 C6 59.65(15) . . . . ?
O2 O1 C7 C8 -177.29(11) . . . . ?
O2 O1 C7 C13 -57.45(15) . . . . ?
C5 C6 C7 O1 54.7(2) . . . . ?
C1 C6 C7 O1 -128.59(15) . . . . ?
C5 C6 C7 C8 -64.1(2) . . . . ?
C1 C6 C7 C8 112.69(16) . . . . ?
C5 C6 C7 C13 177.90(17) . . . . ?
C1 C6 C7 C13 -5.33(16) . . . . ?
O1 O2 C9 C11 -176.77(12) . . . . ?
O1 O2 C9 C10 65.82(16) . . . . ?
O1 O2 C9 C12 -58.33(16) . . . . ?
C1 N1 C13 C14 177.15(15) . . . . ?
C1 N1 C13 C7 -5.16(17) . . . . ?
O1 C7 C13 N1 131.33(14) . . . . ?
C6 C7 C13 N1 6.30(16) . . . . ?
C8 C7 C13 N1 -112.72(15) . . . . ?
O1 C7 C13 C14 -51.0(2) . . . . ?
C6 C7 C13 C14 -175.99(15) . . . . ?
C8 C7 C13 C14 64.99(19) . . . . ?
N1 C13 C14 C15 -173.17(15) . . . . ?
C7 C13 C14 C15 9.5(2) . . . . ?
N1 C13 C14 C16 4.9(3) . . . . ?
C7 C13 C14 C16 -172.42(15) . . . . ?
C17 O4 C16 O3 0.6(2) . . . . ?
C17 O4 C16 C14 -178.82(15) . . . . ?
C13 C14 C16 O3 2.0(3) . . . . ?
C15 C14 C16 O3 -179.90(16) . . . . ?
C13 C14 C16 O4 -178.61(14) . . . . ?
C15 C14 C16 O4 -0.5(2) . . . . ?
