#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:19:43 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234180 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/47/7124739.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_7124739
loop_
_publ_author_name
'Singh, RahulKumar Rajmani'
'Pawar, Samir Kundlik'
'Huang, Min-Jie'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides
 and allenamides to yield 1-amino-1H-indenes.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11434
_journal_page_last               11437
_journal_paper_doi               10.1039/c6cc04308a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C18 H17 N O4 S'
_chemical_formula_weight         343.38
_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-2014/6
_audit_update_record
;
2016-03-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                113.781(3)
_cell_angle_beta                 98.198(3)
_cell_angle_gamma                93.092(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5556(3)
_cell_length_b                   11.4813(6)
_cell_length_c                   12.6356(7)
_cell_measurement_reflns_used    2863
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.9559
_cell_measurement_theta_min      3.1520
_cell_volume                     854.85(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12221
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         1.790
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0916P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2607
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc04308a2.cif
_cod_data_source_block           160104_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7124739
_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.
;
_shelxl_version_number           2014/6
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
C1 C 0.2519(3) 0.9682(2) 0.4726(2) 0.0364(5) Uani 1 1 d . .
C2 C 0.2624(3) 0.8288(2) 0.43531(19) 0.0349(5) Uani 1 1 d . .
C3 C 0.3131(3) 0.7819(2) 0.3283(2) 0.0346(5) Uani 1 1 d . .
C4 C 0.3420(3) 0.8888(2) 0.28972(19) 0.0340(5) Uani 1 1 d . .
H4 H 0.4877 0.9017 0.2828 0.041 Uiso 1 1 calc R U
C5 C 0.2850(5) 1.0774(3) 0.1391(3) 0.0662(8) Uani 1 1 d . .
H5A H 0.3424 1.1098 0.0891 0.099 Uiso 1 1 calc R U
H5B H 0.3606 1.1212 0.2181 0.099 Uiso 1 1 calc R U
H5C H 0.1418 1.0912 0.1377 0.099 Uiso 1 1 calc R U
C6 C -0.0139(3) 0.8489(3) 0.1734(2) 0.0630(8) Uani 1 1 d . .
H6A H -0.0451 0.8139 0.2275 0.095 Uiso 1 1 calc R U
H6B H -0.0793 0.7916 0.0950 0.095 Uiso 1 1 calc R U
H6C H -0.0651 0.9306 0.1937 0.095 Uiso 1 1 calc R U
C7 C 0.2376(3) 0.7637(2) 0.5131(2) 0.0401(5) Uani 1 1 d . .
C8 C 0.3898(4) 0.6938(3) 0.5358(2) 0.0512(7) Uani 1 1 d . .
H8 H 0.5080 0.6886 0.5020 0.061 Uiso 1 1 calc R U
C9 C 0.3687(5) 0.6320(3) 0.6076(3) 0.0650(8) Uani 1 1 d . .
H9 H 0.4733 0.5864 0.6230 0.078 Uiso 1 1 calc R U
C10 C 0.1959(5) 0.6373(3) 0.6559(3) 0.0749(9) Uani 1 1 d . .
H10 H 0.1823 0.5955 0.7045 0.090 Uiso 1 1 calc R U
C11 C 0.0418(6) 0.7037(4) 0.6335(3) 0.0887(12) Uani 1 1 d . .
H11 H -0.0777 0.7056 0.6657 0.106 Uiso 1 1 calc R U
C12 C 0.0625(5) 0.7683(3) 0.5631(3) 0.0693(9) Uani 1 1 d . .
H12 H -0.0418 0.8150 0.5495 0.083 Uiso 1 1 calc R U
C13 C 0.3435(3) 0.6500(2) 0.25305(19) 0.0376(5) Uani 1 1 d . .
C14 C 0.1927(4) 0.5489(2) 0.2296(2) 0.0547(7) Uani 1 1 d . .
H14 H 0.0735 0.5643 0.2626 0.066 Uiso 1 1 calc R U
C15 C 0.2203(5) 0.4253(3) 0.1571(3) 0.0711(9) Uani 1 1 d . .
H15 H 0.1179 0.3580 0.1403 0.085 Uiso 1 1 calc R U
C16 C 0.3946(5) 0.4013(3) 0.1104(3) 0.0658(8) Uani 1 1 d . .
H16 H 0.4118 0.3178 0.0620 0.079 Uiso 1 1 calc R U
C17 C 0.5473(5) 0.5007(3) 0.1344(3) 0.0656(8) Uani 1 1 d . .
H17 H 0.6685 0.4841 0.1035 0.079 Uiso 1 1 calc R U
C18 C 0.5193(4) 0.6243(3) 0.2041(2) 0.0532(7) Uani 1 1 d . .
H18 H 0.6206 0.6913 0.2183 0.064 Uiso 1 1 calc R U
N1 N 0.2123(2) 0.86541(18) 0.17981(16) 0.0385(5) Uani 1 1 d . .
O1 O 0.1688(3) 0.8500(2) -0.02175(15) 0.0653(6) Uani 1 1 d . .
O2 O 0.5178(2) 0.89701(19) 0.09795(16) 0.0557(5) Uani 1 1 d . .
O3 O 0.2956(2) 1.00113(14) 0.38491(13) 0.0380(4) Uani 1 1 d . .
O4 O 0.2202(2) 1.04775(15) 0.56377(14) 0.0422(4) Uani 1 1 d . .
S1 S 0.30377(8) 0.91417(6) 0.08924(5) 0.0405(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'
S S 0.1246 0.1234 '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
O4 C1 O3 121.1(2)
O4 C1 C2 130.1(2)
O3 C1 C2 108.80(19)
C3 C2 C7 129.1(2)
C3 C2 C1 108.00(19)
C7 C2 C1 122.73(19)
C2 C3 C13 129.5(2)
C2 C3 C4 109.37(19)
C13 C3 C4 121.08(19)
N1 C4 O3 111.61(17)
N1 C4 C3 113.43(17)
O3 C4 C3 104.63(17)
N1 C4 H4 109.0
O3 C4 H4 109.0
C3 C4 H4 109.0
S1 C5 H5A 109.5
S1 C5 H5B 109.5
H5A C5 H5B 109.5
S1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C12 C7 C8 118.3(2)
C12 C7 C2 121.6(2)
C8 C7 C2 120.09(19)
C9 C8 C7 120.9(2)
C9 C8 H8 119.6
C7 C8 H8 119.6
C10 C9 C8 120.1(3)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 120.3(3)
C9 C10 H10 119.9
C11 C10 H10 119.9
C10 C11 C12 120.2(3)
C10 C11 H11 119.9
C12 C11 H11 119.9
C7 C12 C11 120.1(3)
C7 C12 H12 119.9
C11 C12 H12 119.9
C18 C13 C14 118.8(2)
C18 C13 C3 121.1(2)
C14 C13 C3 120.0(2)
C15 C14 C13 119.8(3)
C15 C14 H14 120.1
C13 C14 H14 120.1
C16 C15 C14 120.7(3)
C16 C15 H15 119.7
C14 C15 H15 119.7
C15 C16 C17 120.1(3)
C15 C16 H16 120.0
C17 C16 H16 120.0
C18 C17 C16 119.7(3)
C18 C17 H17 120.1
C16 C17 H17 120.1
C17 C18 C13 120.8(2)
C17 C18 H18 119.6
C13 C18 H18 119.6
C4 N1 C6 117.48(17)
C4 N1 S1 118.96(13)
C6 N1 S1 118.81(16)
C1 O3 C4 109.16(16)
O2 S1 O1 119.15(12)
O2 S1 N1 106.86(10)
O1 S1 N1 106.59(10)
O2 S1 C5 108.22(14)
O1 S1 C5 108.10(14)
N1 S1 C5 107.37(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O4 1.202(3)
C1 O3 1.367(3)
C1 C2 1.484(3)
C2 C3 1.337(3)
C2 C7 1.476(3)
C3 C13 1.471(3)
C3 C4 1.505(3)
C4 N1 1.436(3)
C4 O3 1.448(3)
C4 H4 0.9800
C5 S1 1.737(3)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 N1 1.472(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C12 1.381(3)
C7 C8 1.382(3)
C8 C9 1.375(3)
C8 H8 0.9300
C9 C10 1.354(4)
C9 H9 0.9300
C10 C11 1.362(5)
C10 H10 0.9300
C11 C12 1.384(4)
C11 H11 0.9300
C12 H12 0.9300
C13 C18 1.375(3)
C13 C14 1.388(3)
C14 C15 1.383(4)
C14 H14 0.9300
C15 C16 1.351(4)
C15 H15 0.9300
C16 C17 1.381(4)
C16 H16 0.9300
C17 C18 1.374(4)
C17 H17 0.9300
C18 H18 0.9300
N1 S1 1.6305(18)
O1 S1 1.4267(18)
O2 S1 1.4225(17)
