#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516712.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_1516712
loop_
_publ_author_name
'Feng, Xin'
'Wang, Huiqing'
'Yang, Bo'
'Fan, Renhua'
_publ_section_title
;
 One-Pot Synthesis of Highly Substituted 4-Acetonylindoles via Sequential
 Dearomatization and Silver-Catalyzed Domino Reaction.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3600
_journal_page_last               3603
_journal_paper_doi               10.1021/ol501678v
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C28 H27 N O3 S'
_chemical_formula_weight         457.56
_chemical_name_systematic
; 
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.843(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.055(5)
_cell_length_b                   8.557(4)
_cell_length_c                   23.454(10)
_cell_measurement_reflns_used    917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.451
_cell_measurement_theta_min      2.920
_cell_volume                     2419.1(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9745
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.737
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  -0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0772
_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)+(0.1549P)²] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2615
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol501678v_si_002.cif
_cod_data_source_block           a31203a
_cod_depositor_comments          'Adding full bibliography for 1516712.cif.'
_cod_database_code               1516712
#BEGIN Tags that were not found in dictionaries:
_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   0.913
_shelx_estimated_absorpt_t_max   0.938
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
S1 S -0.10934(7) 0.15420(11) 0.14716(4) 0.0753(4) Uani 1 1 d . .
N1 N -0.0569(2) 0.3165(3) 0.11999(11) 0.0672(7) Uani 1 1 d . .
O1 O -0.19887(18) 0.1970(3) 0.18219(11) 0.0899(8) Uani 1 1 d . .
O2 O -0.1284(2) 0.0534(3) 0.10010(11) 0.0955(8) Uani 1 1 d . .
O3 O 0.3591(2) 0.5445(3) 0.07644(12) 0.0977(9) Uani 1 1 d . .
C1 C -0.0481(3) 0.4643(4) 0.14886(14) 0.0682(8) Uani 1 1 d . .
C2 C 0.0252(3) 0.5506(4) 0.12068(13) 0.0673(8) Uani 1 1 d . .
H2 H 0.0444 0.6529 0.1300 0.081 Uiso 1 1 calc R U
C3 C 0.0701(2) 0.4650(4) 0.07457(12) 0.0611(8) Uani 1 1 d . .
C4 C 0.1477(2) 0.5026(4) 0.03333(13) 0.0642(8) Uani 1 1 d . .
C5 C 0.1743(3) 0.3913(4) -0.00750(13) 0.0689(9) Uani 1 1 d . .
C6 C 0.1206(3) 0.2455(5) -0.00568(14) 0.0749(9) Uani 1 1 d . .
H6 H 0.1386 0.1711 -0.0329 0.090 Uiso 1 1 calc R U
C7 C 0.0432(3) 0.2075(4) 0.03410(14) 0.0710(9) Uani 1 1 d . .
H7 H 0.0083 0.1106 0.0335 0.085 Uiso 1 1 calc R U
C8 C 0.0185(2) 0.3177(4) 0.07520(13) 0.0639(8) Uani 1 1 d . .
C9 C -0.1158(3) 0.5060(5) 0.19763(17) 0.0886(11) Uani 1 1 d . .
H9 H -0.1944 0.4783 0.1938 0.106 Uiso 1 1 calc R U
C10 C -0.0937(6) 0.6529(7) 0.2287(3) 0.143(2) Uani 1 1 d . U
H10A H -0.0304 0.7148 0.2173 0.171 Uiso 1 1 calc R U
H10B H -0.1568 0.7127 0.2416 0.171 Uiso 1 1 calc R U
C11 C -0.0721(6) 0.5025(11) 0.2555(3) 0.168(3) Uani 1 1 d . .
H11A H 0.0047 0.4715 0.2611 0.202 Uiso 1 1 calc R U
H11B H -0.1216 0.4693 0.2854 0.202 Uiso 1 1 calc R U
C12 C 0.2004(2) 0.6607(4) 0.03391(14) 0.0686(9) Uani 1 1 d . .
H12A H 0.1528 0.7322 0.0544 0.082 Uiso 1 1 calc R U
H12B H 0.2053 0.6980 -0.0050 0.082 Uiso 1 1 calc R U
C13 C 0.3146(3) 0.6649(4) 0.06092(13) 0.0658(8) Uani 1 1 d . .
C14 C 0.3722(2) 0.8165(4) 0.06798(13) 0.0635(8) Uani 1 1 d . .
C15 C 0.3237(3) 0.9586(4) 0.05587(15) 0.0744(9) Uani 1 1 d . .
H15 H 0.2508 0.9610 0.0423 0.089 Uiso 1 1 calc R U
C16 C 0.3803(3) 1.0974(5) 0.06338(16) 0.0822(10) Uani 1 1 d . .
H16 H 0.3448 1.1917 0.0557 0.099 Uiso 1 1 calc R U
C17 C 0.4888(3) 1.0976(5) 0.08214(14) 0.0743(9) Uani 1 1 d . .
C18 C 0.5385(3) 0.9548(5) 0.09362(16) 0.0819(10) Uani 1 1 d . .
H18 H 0.6120 0.9521 0.1062 0.098 Uiso 1 1 calc R U
C19 C 0.4811(3) 0.8174(5) 0.08683(15) 0.0779(10) Uani 1 1 d . .
H19 H 0.5163 0.7232 0.0951 0.093 Uiso 1 1 calc R U
C20 C 0.5520(3) 1.2478(5) 0.08951(19) 0.0989(12) Uani 1 1 d . .
H20A H 0.5483 1.2811 0.1285 0.148 Uiso 1 1 calc R U
H20B H 0.5199 1.3266 0.0652 0.148 Uiso 1 1 calc R U
H20C H 0.6280 1.2317 0.0795 0.148 Uiso 1 1 calc R U
C21 C 0.2593(3) 0.4218(6) -0.05173(16) 0.0929(12) Uani 1 1 d . .
H21A H 0.2419 0.5174 -0.0713 0.139 Uiso 1 1 calc R U
H21B H 0.2597 0.3370 -0.0786 0.139 Uiso 1 1 calc R U
H21C H 0.3312 0.4304 -0.0338 0.139 Uiso 1 1 calc R U
C22 C -0.0041(3) 0.0742(4) 0.18988(15) 0.0700(8) Uani 1 1 d . .
C23 C 0.0841(3) -0.0041(4) 0.16566(16) 0.0802(10) Uani 1 1 d . .
H23 H 0.0889 -0.0119 0.1262 0.096 Uiso 1 1 calc R U
C24 C 0.1640(3) -0.0697(5) 0.19991(19) 0.0893(11) Uani 1 1 d . .
H24 H 0.2235 -0.1205 0.1833 0.107 Uiso 1 1 calc R U
C25 C 0.1586(3) -0.0627(5) 0.25847(19) 0.0873(11) Uani 1 1 d . .
C26 C 0.0712(4) 0.0167(5) 0.28196(17) 0.0923(12) Uani 1 1 d . .
H26 H 0.0668 0.0246 0.3214 0.111 Uiso 1 1 calc R U
C27 C -0.0096(3) 0.0846(5) 0.24841(16) 0.0835(10) Uani 1 1 d . .
H27 H -0.0681 0.1375 0.2652 0.100 Uiso 1 1 calc R U
C28 C 0.2450(4) -0.1410(7) 0.2958(2) 0.1243(18) Uani 1 1 d . .
H28A H 0.3040 -0.1791 0.2726 0.187 Uiso 1 1 calc R U
H28B H 0.2118 -0.2267 0.3157 0.187 Uiso 1 1 calc R U
H28C H 0.2740 -0.0669 0.3229 0.187 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 0.0033 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
O1 S1 O2 119.61(16)
O1 S1 N1 107.76(15)
O2 S1 N1 105.60(16)
O1 S1 C22 108.83(17)
O2 S1 C22 108.45(18)
N1 S1 C22 105.73(15)
C8 N1 C1 107.6(3)
C8 N1 S1 123.4(2)
C1 N1 S1 125.6(2)
C2 C1 N1 107.4(3)
C2 C1 C9 129.4(3)
N1 C1 C9 123.1(3)
C1 C2 C3 110.7(3)
C4 C3 C8 121.0(3)
C4 C3 C2 132.6(3)
C8 C3 C2 106.3(3)
C5 C4 C3 119.0(3)
C5 C4 C12 121.5(3)
C3 C4 C12 119.5(3)
C4 C5 C6 118.4(3)
C4 C5 C21 121.8(4)
C6 C5 C21 119.8(3)
C7 C6 C5 123.4(3)
C6 C7 C8 118.0(3)
C7 C8 N1 131.8(3)
C7 C8 C3 120.3(3)
N1 C8 C3 107.9(3)
C11 C9 C1 122.0(4)
C11 C9 C10 59.6(4)
C1 C9 C10 119.8(4)
C11 C10 C9 59.3(3)
C9 C11 C10 61.1(4)
C4 C12 C13 114.2(3)
O3 C13 C14 120.4(3)
O3 C13 C12 120.2(3)
C14 C13 C12 119.5(3)
C15 C14 C19 117.5(3)
C15 C14 C13 123.6(3)
C19 C14 C13 118.9(3)
C14 C15 C16 121.7(3)
C17 C16 C15 120.6(4)
C16 C17 C18 117.9(4)
C16 C17 C20 121.1(4)
C18 C17 C20 121.0(3)
C19 C18 C17 121.2(3)
C18 C19 C14 121.1(3)
C27 C22 C23 119.2(3)
C27 C22 S1 120.1(3)
C23 C22 S1 120.7(3)
C24 C23 C22 119.8(4)
C23 C24 C25 121.7(4)
C26 C25 C24 117.9(4)
C26 C25 C28 120.9(4)
C24 C25 C28 121.2(4)
C27 C26 C25 121.4(4)
C26 C27 C22 120.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.414(3)
S1 O2 1.417(3)
S1 N1 1.657(3)
S1 C22 1.745(4)
N1 C8 1.399(4)
N1 C1 1.438(4)
O3 C13 1.215(4)
C1 C2 1.335(5)
C1 C9 1.459(5)
C2 C3 1.420(4)
C3 C4 1.393(4)
C3 C8 1.406(4)
C4 C5 1.391(4)
C4 C12 1.495(5)
C5 C6 1.406(5)
C5 C21 1.492(5)
C6 C7 1.368(5)
C7 C8 1.384(4)
C9 C11 1.449(7)
C9 C10 1.475(6)
C10 C11 1.454(9)
C12 C13 1.507(4)
C13 C14 1.480(5)
C14 C15 1.377(4)
C14 C19 1.380(4)
C15 C16 1.381(5)
C16 C17 1.374(5)
C17 C18 1.385(5)
C17 C20 1.503(6)
C18 C19 1.372(5)
C22 C27 1.378(5)
C22 C23 1.386(5)
C23 C24 1.365(5)
C24 C25 1.377(6)
C25 C26 1.375(6)
C25 C28 1.508(6)
C26 C27 1.372(5)
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
O1 S1 N1 C8 -167.5(2)
O2 S1 N1 C8 -38.6(3)
C22 S1 N1 C8 76.3(3)
O1 S1 N1 C1 35.9(3)
O2 S1 N1 C1 164.8(3)
C22 S1 N1 C1 -80.4(3)
C8 N1 C1 C2 2.7(3)
S1 N1 C1 C2 162.4(2)
C8 N1 C1 C9 179.2(3)
S1 N1 C1 C9 -21.1(4)
N1 C1 C2 C3 -2.0(4)
C9 C1 C2 C3 -178.2(3)
C1 C2 C3 C4 179.8(3)
C1 C2 C3 C8 0.6(3)
C8 C3 C4 C5 -0.3(4)
C2 C3 C4 C5 -179.4(3)
C8 C3 C4 C12 179.7(3)
C2 C3 C4 C12 0.6(5)
C3 C4 C5 C6 0.6(4)
C12 C4 C5 C6 -179.4(3)
C3 C4 C5 C21 -178.0(3)
C12 C4 C5 C21 1.9(4)
C4 C5 C6 C7 0.2(5)
C21 C5 C6 C7 178.8(3)
C5 C6 C7 C8 -1.3(5)
C6 C7 C8 N1 178.3(3)
C6 C7 C8 C3 1.6(4)
C1 N1 C8 C7 -179.3(3)
S1 N1 C8 C7 20.5(4)
C1 N1 C8 C3 -2.3(3)
S1 N1 C8 C3 -162.5(2)
C4 C3 C8 C7 -0.8(4)
C2 C3 C8 C7 178.5(3)
C4 C3 C8 N1 -178.2(2)
C2 C3 C8 N1 1.1(3)
C2 C1 C9 C11 -81.6(7)
N1 C1 C9 C11 102.8(6)
C2 C1 C9 C10 -10.8(7)
N1 C1 C9 C10 173.5(5)
C1 C9 C10 C11 -111.9(5)
C1 C9 C11 C10 108.2(5)
C5 C4 C12 C13 -80.5(4)
C3 C4 C12 C13 99.4(3)
C4 C12 C13 O3 4.9(5)
C4 C12 C13 C14 -175.5(3)
O3 C13 C14 C15 -174.4(3)
C12 C13 C14 C15 6.1(5)
O3 C13 C14 C19 6.7(5)
C12 C13 C14 C19 -172.9(3)
C19 C14 C15 C16 -1.4(5)
C13 C14 C15 C16 179.6(3)
C14 C15 C16 C17 1.5(6)
C15 C16 C17 C18 -0.6(5)
C15 C16 C17 C20 178.9(3)
C16 C17 C18 C19 -0.4(6)
C20 C17 C18 C19 -179.9(4)
C17 C18 C19 C14 0.4(6)
C15 C14 C19 C18 0.5(5)
C13 C14 C19 C18 179.5(3)
O1 S1 C22 C27 -10.4(4)
O2 S1 C22 C27 -142.0(3)
N1 S1 C22 C27 105.2(3)
O1 S1 C22 C23 167.7(3)
O2 S1 C22 C23 36.1(3)
N1 S1 C22 C23 -76.7(3)
C27 C22 C23 C24 0.0(6)
S1 C22 C23 C24 -178.1(3)
C22 C23 C24 C25 1.1(6)
C23 C24 C25 C26 -1.7(6)
C23 C24 C25 C28 177.7(4)
C24 C25 C26 C27 1.3(7)
C28 C25 C26 C27 -178.1(4)
C25 C26 C27 C22 -0.2(7)
C23 C22 C27 C26 -0.5(6)
S1 C22 C27 C26 177.7(3)
