#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:36:13 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/73/4037378.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_4037378
loop_
_publ_author_name
'Xu, Dongdong'
'Sun, Wen-Wu'
'Xie, Yanli'
'Liu, Ji-Kai'
'Liu, Bin'
'Zhou, Yingbi'
'Wu, Bin'
_publ_section_title
;
 Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3
 Difunctionalization of N-Substituted Indoles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11081
_journal_page_last               11094
_journal_paper_doi               10.1021/acs.joc.6b02078
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C14 H11 N3 O3'
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.542(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2007(14)
_cell_length_b                   7.0368(10)
_cell_length_c                   17.310(2)
_cell_measurement_reflns_used    6462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.25
_cell_measurement_theta_min      2.39
_cell_volume                     1225.3(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12607
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.8162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          2.00
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3044
_reflns_number_total             3432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02078_si_002.cif
_cod_data_source_block           mo_bwxd7_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1225.4(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037378
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.75310(7) 0.41803(11) 0.95340(4) 0.01663(16) Uani 1 1 d .
O2 O 0.70797(8) 0.40392(12) 1.07686(4) 0.02501(19) Uani 1 1 d .
O3 O 0.77609(8) 0.82609(12) 0.96467(5) 0.02487(19) Uani 1 1 d .
N1 N 0.56692(8) 0.48787(12) 0.85637(5) 0.01447(17) Uani 1 1 d .
N2 N 0.49030(8) 0.22559(12) 0.91576(5) 0.01563(18) Uani 1 1 d .
N3 N 0.41327(8) 0.29192(12) 0.77974(5) 0.01635(18) Uani 1 1 d .
C1 C 0.89811(11) 0.23778(16) 1.04452(7) 0.0238(2) Uani 1 1 d .
H1A H 0.9253 0.2204 1.1011 0.036 Uiso 1 1 calc R
H1B H 0.9702 0.2988 1.0227 0.036 Uiso 1 1 calc R
H1C H 0.8783 0.1138 1.0195 0.036 Uiso 1 1 calc R
C2 C 0.77675(10) 0.36052(14) 1.02962(6) 0.0177(2) Uani 1 1 d .
C3 C 0.64236(9) 0.54314(14) 0.93144(5) 0.01487(19) Uani 1 1 d .
H3 H 0.5848 0.5490 0.9728 0.018 Uiso 1 1 calc R
C4 C 0.48551(9) 0.32830(13) 0.84988(5) 0.01332(18) Uani 1 1 d .
C5 C 0.41349(10) 0.07023(14) 0.90873(6) 0.01623(19) Uani 1 1 d .
H5 H 0.4123 -0.0064 0.9538 0.019 Uiso 1 1 calc R
C6 C 0.33558(10) 0.01579(14) 0.83892(6) 0.0169(2) Uani 1 1 d .
H6 H 0.2829 -0.0962 0.8349 0.020 Uiso 1 1 calc R
C7 C 0.33893(10) 0.13381(14) 0.77535(6) 0.0175(2) Uani 1 1 d .
H7 H 0.2864 0.1015 0.7265 0.021 Uiso 1 1 calc R
C8 C 0.56864(9) 0.63525(14) 0.80138(6) 0.01456(19) Uani 1 1 d .
C9 C 0.64644(9) 0.78776(14) 0.83506(6) 0.0165(2) Uani 1 1 d .
C10 C 0.66732(10) 0.95006(15) 0.79248(7) 0.0209(2) Uani 1 1 d .
H10 H 0.7215 1.0510 0.8161 0.025 Uiso 1 1 calc R
C11 C 0.60696(11) 0.96023(16) 0.71479(7) 0.0235(2) Uani 1 1 d .
H11 H 0.6192 1.0692 0.6844 0.028 Uiso 1 1 calc R
C12 C 0.52802(11) 0.80968(16) 0.68140(6) 0.0219(2) Uani 1 1 d .
H12 H 0.4867 0.8195 0.6282 0.026 Uiso 1 1 calc R
C13 C 0.50738(10) 0.64545(15) 0.72297(6) 0.0178(2) Uani 1 1 d .
H13 H 0.4538 0.5444 0.6989 0.021 Uiso 1 1 calc R
C14 C 0.69875(10) 0.74023(14) 0.91616(6) 0.0168(2) Uani 1 1 d .
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'
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
C2 O1 C3 116.40(8)
C4 N1 C8 127.87(8)
C4 N1 C3 120.69(8)
C8 N1 C3 110.11(8)
C5 N2 C4 115.06(8)
C4 N3 C7 115.57(8)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 O1 123.62(10)
O2 C2 C1 126.09(10)
O1 C2 C1 110.29(9)
O1 C3 N1 110.56(8)
O1 C3 C14 107.35(7)
N1 C3 C14 104.21(8)
O1 C3 H3 111.5
N1 C3 H3 111.5
C14 C3 H3 111.5
N3 C4 N2 127.21(9)
N3 C4 N1 117.40(8)
N2 C4 N1 115.38(8)
N2 C5 C6 123.18(9)
N2 C5 H5 118.4
C6 C5 H5 118.4
C7 C6 C5 116.20(9)
C7 C6 H6 121.9
C5 C6 H6 121.9
N3 C7 C6 122.76(9)
N3 C7 H7 118.6
C6 C7 H7 118.6
C13 C8 C9 119.67(9)
C13 C8 N1 129.74(9)
C9 C8 N1 110.59(8)
C10 C9 C8 122.16(10)
C10 C9 C14 129.35(10)
C8 C9 C14 108.47(9)
C11 C10 C9 118.24(10)
C11 C10 H10 120.9
C9 C10 H10 120.9
C10 C11 C12 119.72(10)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 122.72(10)
C13 C12 H12 118.6
C11 C12 H12 118.6
C12 C13 C8 117.48(10)
C12 C13 H13 121.3
C8 C13 H13 121.3
O3 C14 C9 130.18(10)
O3 C14 C3 123.20(10)
C9 C14 C3 106.54(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3628(12)
O1 C3 1.4330(12)
O2 C2 1.2017(14)
O3 C14 1.2137(13)
N1 C4 1.3900(12)
N1 C8 1.4097(12)
N1 C3 1.4493(12)
N2 C5 1.3388(13)
N2 C4 1.3441(12)
N3 C4 1.3366(12)
N3 C7 1.3414(13)
C1 C2 1.4964(15)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C3 C14 1.5410(14)
C3 H3 1.0000
C5 C6 1.3858(13)
C5 H5 0.9500
C6 C7 1.3835(14)
C6 H6 0.9500
C7 H7 0.9500
C8 C13 1.3989(13)
C8 C9 1.4028(14)
C9 C10 1.3947(14)
C9 C14 1.4557(14)
C10 C11 1.3850(16)
C10 H10 0.9500
C11 C12 1.3967(17)
C11 H11 0.9500
C12 C13 1.3956(14)
C12 H12 0.9500
C13 H13 0.9500
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
C3 O1 C2 O2 2.57(14)
C3 O1 C2 C1 -177.64(8)
C2 O1 C3 N1 -137.14(8)
C2 O1 C3 C14 109.80(9)
C4 N1 C3 O1 74.15(11)
C8 N1 C3 O1 -118.01(8)
C4 N1 C3 C14 -170.80(8)
C8 N1 C3 C14 -2.96(10)
C7 N3 C4 N2 -0.76(15)
C7 N3 C4 N1 178.17(9)
C5 N2 C4 N3 0.12(14)
C5 N2 C4 N1 -178.83(8)
C8 N1 C4 N3 10.89(14)
C3 N1 C4 N3 176.37(8)
C8 N1 C4 N2 -170.05(9)
C3 N1 C4 N2 -4.57(13)
C4 N2 C5 C6 0.85(14)
N2 C5 C6 C7 -1.08(15)
C4 N3 C7 C6 0.47(15)
C5 C6 C7 N3 0.37(15)
C4 N1 C8 C13 -11.80(16)
C3 N1 C8 C13 -178.53(10)
C4 N1 C8 C9 168.78(9)
C3 N1 C8 C9 2.05(11)
C13 C8 C9 C10 -1.16(15)
N1 C8 C9 C10 178.32(9)
C13 C8 C9 C14 -179.60(9)
N1 C8 C9 C14 -0.11(11)
C8 C9 C10 C11 1.02(15)
C14 C9 C10 C11 179.10(10)
C9 C10 C11 C12 -0.15(16)
C10 C11 C12 C13 -0.59(17)
C11 C12 C13 C8 0.45(16)
C9 C8 C13 C12 0.41(14)
N1 C8 C13 C12 -178.97(9)
C10 C9 C14 O3 -3.12(18)
C8 C9 C14 O3 175.17(11)
C10 C9 C14 C3 180.00(10)
C8 C9 C14 C3 -1.72(10)
O1 C3 C14 O3 -57.04(12)
N1 C3 C14 O3 -174.34(9)
O1 C3 C14 C9 120.11(8)
N1 C3 C14 C9 2.82(10)
