#------------------------------------------------------------------------------
#$Date: 2018-02-13 02:46:26 +0200 (Tue, 13 Feb 2018) $
#$Revision: 206371 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127173.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_4127173
loop_
_publ_author_name
'Xu, Hai'
'He, Jia'
'Shi, Jiarong'
'Tan, Liang'
'Qiu, Dachuan'
'Luo, Xiaohua'
'Li, Yang'
_publ_section_title
;
 Domino Aryne Annulation via Nucleophilic-Ene Process.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.8b01005
_journal_year                    2018
_chemical_formula_sum            'C24 H29 N O2 S'
_chemical_formula_weight         395.54
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.662(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5226(3)
_cell_length_b                   15.1939(6)
_cell_length_c                   14.7465(6)
_cell_measurement_reflns_used    3528
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.08
_cell_measurement_theta_min      3.45
_cell_volume                     2103.34(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9382
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+0.6932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                3528
_reflns_number_total             4841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b01005_si_004.cif
_cod_data_source_block           xh-9-35-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4127173
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.43111(6) 0.12424(3) 0.33997(4) 0.04546(17) Uani 1 1 d .
N1 N 0.50005(16) 0.02956(10) 0.31926(11) 0.0382(4) Uani 1 1 d .
C5 C 0.3262(2) 0.16209(12) 0.23695(14) 0.0396(4) Uani 1 1 d .
C8 C 0.41123(19) -0.04808(12) 0.31388(13) 0.0351(4) Uani 1 1 d .
C14 C 0.4134(2) -0.04886(12) 0.14420(13) 0.0378(4) Uani 1 1 d .
H14A H 0.4081 0.0153 0.1495 0.045 Uiso 1 1 calc R
O1 O 0.33544(18) 0.10979(11) 0.40364(11) 0.0627(5) Uani 1 1 d .
C12 C 0.2809(2) -0.16198(13) 0.22601(15) 0.0416(5) Uani 1 1 d .
H12A H 0.2487 -0.1893 0.1699 0.050 Uiso 1 1 calc R
O2 O 0.54667(18) 0.18438(10) 0.36233(12) 0.0628(5) Uani 1 1 d .
C13 C 0.36348(18) -0.08638(12) 0.22845(13) 0.0343(4) Uani 1 1 d .
C19 C 0.6687(2) -0.05784(14) 0.23936(15) 0.0449(5) Uani 1 1 d .
H19A H 0.6558 -0.1084 0.2784 0.054 Uiso 1 1 calc R
C24 C 0.6464(2) 0.02573(13) 0.29386(14) 0.0419(5) Uani 1 1 d .
H24A H 0.6587 0.0771 0.2557 0.050 Uiso 1 1 calc R
C15 C 0.3184(2) -0.07335(13) 0.05483(14) 0.0452(5) Uani 1 1 d .
C10 C 0.2946(2) -0.15876(14) 0.38937(16) 0.0495(5) Uani 1 1 d .
H10A H 0.2710 -0.1829 0.4428 0.059 Uiso 1 1 calc R
C9 C 0.3783(2) -0.08441(14) 0.39387(14) 0.0426(5) Uani 1 1 d .
H9A H 0.4125 -0.0587 0.4505 0.051 Uiso 1 1 calc R
C18 C 0.5711(2) -0.07143(15) 0.14754(15) 0.0467(5) Uani 1 1 d .
H18A H 0.5776 -0.1326 0.1299 0.056 Uiso 1 1 calc R
H18B H 0.6070 -0.0361 0.1016 0.056 Uiso 1 1 calc R
C4 C 0.1813(2) 0.14840(15) 0.22151(17) 0.0515(6) Uani 1 1 d .
H4A H 0.1383 0.1187 0.2647 0.062 Uiso 1 1 calc R
C6 C 0.3890(2) 0.20636(13) 0.17192(16) 0.0472(5) Uani 1 1 d .
H6A H 0.4868 0.2160 0.1823 0.057 Uiso 1 1 calc R
C2 C 0.1611(2) 0.22279(14) 0.07519(17) 0.0532(6) Uani 1 1 d .
C7 C 0.3073(2) 0.23604(14) 0.09226(17) 0.0523(5) Uani 1 1 d .
H7A H 0.3505 0.2655 0.0490 0.063 Uiso 1 1 calc R
C11 C 0.2460(2) -0.19706(14) 0.30529(17) 0.0497(5) Uani 1 1 d .
H11A H 0.1891 -0.2471 0.3021 0.060 Uiso 1 1 calc R
C20 C 0.8236(2) -0.06018(18) 0.22206(19) 0.0627(7) Uani 1 1 d .
H20A H 0.8393 -0.1153 0.1921 0.075 Uiso 1 1 calc R
H20B H 0.8370 -0.0129 0.1801 0.075 Uiso 1 1 calc R
C17 C 0.3541(3) -0.12761(16) -0.00684(17) 0.0639(7) Uani 1 1 d .
H17A H 0.2905 -0.1389 -0.0607 0.096 Uiso 1 1 calc R
H17B H 0.4429 -0.1547 0.0033 0.096 Uiso 1 1 calc R
C3 C 0.1006(2) 0.17915(16) 0.14144(19) 0.0578(6) Uani 1 1 d .
H3A H 0.0026 0.1703 0.1316 0.069 Uiso 1 1 calc R
C23 C 0.7567(2) 0.03030(18) 0.38120(16) 0.0590(6) Uani 1 1 d .
H23A H 0.7420 0.0837 0.4145 0.071 Uiso 1 1 calc R
H23B H 0.7438 -0.0194 0.4202 0.071 Uiso 1 1 calc R
C16 C 0.1762(3) -0.02909(18) 0.03984(18) 0.0694(7) Uani 1 1 d .
H16A H 0.1221 -0.0482 -0.0177 0.104 Uiso 1 1 calc R
H16B H 0.1891 0.0335 0.0386 0.104 Uiso 1 1 calc R
H16C H 0.1261 -0.0442 0.0890 0.104 Uiso 1 1 calc R
C22 C 0.9079(2) 0.0295(2) 0.3610(2) 0.0700(8) Uani 1 1 d .
H22A H 0.9235 0.0815 0.3259 0.084 Uiso 1 1 calc R
H22B H 0.9747 0.0310 0.4184 0.084 Uiso 1 1 calc R
C21 C 0.9340(3) -0.05122(19) 0.3079(2) 0.0723(8) Uani 1 1 d .
H21A H 0.9311 -0.1028 0.3463 0.087 Uiso 1 1 calc R
H21B H 1.0280 -0.0479 0.2911 0.087 Uiso 1 1 calc R
C1 C 0.0718(3) 0.2549(2) -0.0128(2) 0.0832(9) Uani 1 1 d .
H1B H -0.0264 0.2408 -0.0125 0.125 Uiso 1 1 calc R
H1C H 0.1028 0.2269 -0.0643 0.125 Uiso 1 1 calc R
H1D H 0.0821 0.3175 -0.0175 0.125 Uiso 1 1 calc R
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
O2 S1 O1 119.89(11)
O2 S1 N1 106.81(9)
O1 S1 N1 107.95(9)
O2 S1 C5 107.04(10)
O1 S1 C5 106.48(10)
N1 S1 C5 108.24(9)
C8 N1 C24 120.84(15)
C8 N1 S1 118.66(12)
C24 N1 S1 119.98(13)
C4 C5 C6 119.7(2)
C4 C5 S1 119.93(17)
C6 C5 S1 120.36(16)
C9 C8 C13 121.16(17)
C9 C8 N1 119.49(18)
C13 C8 N1 119.32(16)
C13 C14 C15 113.45(16)
C13 C14 C18 109.27(16)
C15 C14 C18 114.29(17)
C11 C12 C13 121.0(2)
C12 C13 C8 117.80(18)
C12 C13 C14 122.98(18)
C8 C13 C14 119.01(16)
C18 C19 C24 117.36(17)
C18 C19 C20 107.99(18)
C24 C19 C20 109.06(18)
N1 C24 C23 108.95(17)
N1 C24 C19 112.21(15)
C23 C24 C19 110.11(18)
C17 C15 C16 120.9(2)
C17 C15 C14 124.8(2)
C16 C15 C14 114.32(18)
C9 C10 C11 119.6(2)
C10 C9 C8 119.8(2)
C19 C18 C14 116.55(17)
C5 C4 C3 119.4(2)
C7 C6 C5 120.2(2)
C3 C2 C7 117.7(2)
C3 C2 C1 121.4(2)
C7 C2 C1 120.9(2)
C6 C7 C2 121.0(2)
C12 C11 C10 120.58(19)
C21 C20 C19 114.2(2)
C4 C3 C2 121.9(2)
C22 C23 C24 112.1(2)
C21 C22 C23 110.8(2)
C22 C21 C20 111.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4258(16)
S1 O1 1.4306(16)
S1 N1 1.6312(16)
S1 C5 1.768(2)
N1 C8 1.446(2)
N1 C24 1.503(2)
C5 C4 1.376(3)
C5 C6 1.386(3)
C8 C9 1.385(3)
C8 C13 1.393(3)
C14 C13 1.514(3)
C14 C15 1.514(3)
C14 C18 1.533(3)
C12 C11 1.375(3)
C12 C13 1.389(3)
C19 C18 1.523(3)
C19 C24 1.537(3)
C19 C20 1.539(3)
C24 C23 1.521(3)
C15 C17 1.314(3)
C15 C16 1.495(3)
C10 C9 1.378(3)
C10 C11 1.377(3)
C4 C3 1.378(3)
C6 C7 1.372(3)
C2 C3 1.384(3)
C2 C7 1.387(3)
C2 C1 1.508(3)
C20 C21 1.510(4)
C23 C22 1.518(3)
C22 C21 1.498(4)
