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#$Date: 2020-07-10 02:17:08 +0300 (Fri, 10 Jul 2020) $
#$Revision: 254153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038566.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_4038566
loop_
_publ_author_name
'Zhang, Xiaofei'
'Zhu, Peiyuan'
'Zhang, Ruihong'
'Li, Xiang'
'Yao, Tuanli'
_publ_section_title
;
 Visible-light-induced decarboxylative cyclization of
 2-alkenylarylisocyanides with α-oxocarboxylic acids: direct access to
 2-acylindoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00039
_journal_year                    2020
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_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-2014/7
_cell_angle_alpha                111.127(10)
_cell_angle_beta                 92.434(10)
_cell_angle_gamma                96.953(11)
_cell_formula_units_Z            2
_cell_length_a                   6.9345(17)
_cell_length_b                   11.057(3)
_cell_length_c                   11.166(2)
_cell_measurement_reflns_used    620
_cell_measurement_temperature    107(2)
_cell_measurement_theta_max      20.03
_cell_measurement_theta_min      2.97
_cell_volume                     789.3(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      107(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_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  0.1307
_diffrn_reflns_av_unetI/netI     0.2464
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7982
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.972
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.2990
_refine_ls_R_factor_gt           0.1010
_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)+(0.0980P)²+0.0655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.3050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1163
_reflns_number_total             3676
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00039_si_002.cif
_cod_data_source_block           SUST_2136_0m
_cod_database_code               4038566
_shelx_shelxl_version_number     2014/7
_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   0.987
_shelx_estimated_absorpt_t_max   0.989
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
C1 C 0.2130(7) 0.8782(6) 0.3543(5) 0.0555(16) Uani 1 1 d . . . . .
H1 H 0.1803 0.8973 0.2802 0.067 Uiso 1 1 calc R U . . .
C2 C 0.2345(8) 0.9767(6) 0.4741(6) 0.0636(18) Uani 1 1 d . . . . .
H2 H 0.2194 1.0637 0.4831 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2785(8) 0.9468(7) 0.5806(6) 0.069(2) Uani 1 1 d . . . . .
H3 H 0.2930 1.0137 0.6640 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3016(8) 0.8217(6) 0.5676(5) 0.0552(16) Uani 1 1 d . . . . .
H4 H 0.3318 0.8028 0.6422 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2817(7) 0.7227(6) 0.4478(5) 0.0508(15) Uani 1 1 d . . . . .
H5 H 0.2977 0.6360 0.4395 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2382(6) 0.7514(5) 0.3400(5) 0.0394(13) Uani 1 1 d . . . . .
C7 C 0.2025(7) 0.6468(6) 0.2092(5) 0.0453(14) Uani 1 1 d . . . . .
C8 C 0.3198(7) 0.5385(6) 0.1685(5) 0.0442(14) Uani 1 1 d . . . . .
C9 C 0.5065(7) 0.5265(6) 0.2054(5) 0.0445(14) Uani 1 1 d . . . . .
C10 C 0.5386(7) 0.3987(6) 0.1253(5) 0.0473(15) Uani 1 1 d . . . . .
C11 C 0.3669(8) 0.3367(6) 0.0397(5) 0.0482(15) Uani 1 1 d . . . . .
C12 C 0.3491(9) 0.2118(7) -0.0516(5) 0.070(2) Uani 1 1 d . . . . .
H12 H 0.2346 0.1743 -0.1093 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5026(10) 0.1434(7) -0.0561(6) 0.074(2) Uani 1 1 d . . . . .
H13 H 0.4935 0.0556 -0.1155 0.089 Uiso 1 1 calc R U . . .
C14 C 0.6762(9) 0.2038(7) 0.0282(6) 0.074(2) Uani 1 1 d . . . . .
H14 H 0.7835 0.1565 0.0217 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6913(8) 0.3255(6) 0.1164(5) 0.0615(17) Uani 1 1 d . . . . .
H15 H 0.8068 0.3623 0.1733 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6568(7) 0.6274(5) 0.3026(5) 0.0438(14) Uani 1 1 d . . . . .
H16A H 0.7775 0.6360 0.2602 0.053 Uiso 1 1 calc R U . . .
H16B H 0.6084 0.7131 0.3301 0.053 Uiso 1 1 calc R U . . .
C17 C 0.7062(8) 0.5981(7) 0.4189(6) 0.0543(16) Uani 1 1 d . . . . .
C18 C 0.8148(9) 0.6865(6) 0.6416(5) 0.0675(19) Uani 1 1 d . . . . .
H18A H 0.9356 0.6459 0.6342 0.081 Uiso 1 1 calc R U . . .
H18B H 0.7094 0.6286 0.6600 0.081 Uiso 1 1 calc R U . . .
C19 C 0.8468(9) 0.8199(7) 0.7474(5) 0.085(2) Uani 1 1 d . . . . .
H19A H 0.9487 0.8769 0.7268 0.127 Uiso 1 1 calc R U . . .
H19B H 0.8873 0.8119 0.8291 0.127 Uiso 1 1 calc R U . . .
H19C H 0.7251 0.8579 0.7554 0.127 Uiso 1 1 calc R U . . .
N1 N 0.2393(6) 0.4283(5) 0.0682(4) 0.0529(13) Uani 1 1 d . . . . .
H1A H 0.1232 0.4170 0.0274 0.063 Uiso 1 1 calc R U . . .
O1 O 0.0642(5) 0.6463(4) 0.1352(4) 0.0641(12) Uani 1 1 d . . . . .
O2 O 0.7071(8) 0.4910(5) 0.4205(4) 0.0992(18) Uani 1 1 d . . . . .
O3 O 0.7609(5) 0.7048(4) 0.5229(4) 0.0578(11) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(5) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 118.7(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.0(6) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 C7 121.3(5) . . ?
C1 C6 C7 118.9(5) . . ?
O1 C7 C8 119.0(5) . . ?
O1 C7 C6 119.3(5) . . ?
C8 C7 C6 121.6(4) . . ?
N1 C8 C9 110.1(5) . . ?
N1 C8 C7 116.6(4) . . ?
C9 C8 C7 133.2(5) . . ?
C8 C9 C10 106.1(5) . . ?
C8 C9 C16 128.8(5) . . ?
C10 C9 C16 124.9(4) . . ?
C15 C10 C11 117.1(5) . . ?
C15 C10 C9 134.8(5) . . ?
C11 C10 C9 108.0(4) . . ?
C12 C11 N1 131.1(5) . . ?
C12 C11 C10 123.2(5) . . ?
N1 C11 C10 105.7(5) . . ?
C13 C12 C11 117.6(6) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 121.5(6) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 120.5(6) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C9 114.6(5) . . ?
C17 C16 H16A 108.6 . . ?
C9 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C9 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
O2 C17 O3 121.9(5) . . ?
O2 C17 C16 125.0(6) . . ?
O3 C17 C16 113.0(6) . . ?
O3 C18 C19 107.0(5) . . ?
O3 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
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 . . ?
C8 N1 C11 110.0(4) . . ?
C8 N1 H1A 125.0 . . ?
C11 N1 H1A 125.0 . . ?
C17 O3 C18 117.2(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
C1 C2 1.375(8) . ?
C1 C6 1.387(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(7) . ?
C7 O1 1.237(5) . ?
C7 C8 1.476(7) . ?
C8 N1 1.359(6) . ?
C8 C9 1.378(6) . ?
C9 C10 1.425(8) . ?
C9 C16 1.503(7) . ?
C10 C15 1.394(7) . ?
C10 C11 1.426(7) . ?
C11 C12 1.376(8) . ?
C11 N1 1.386(6) . ?
C12 C13 1.371(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.340(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.484(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O2 1.191(7) . ?
C17 O3 1.323(7) . ?
C18 O3 1.451(6) . ?
C18 C19 1.505(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 H1A 0.8800 . ?
