#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025461.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_4025461
loop_
_publ_author_name
'Kristen N. Clary'
'Masood Parvez'
'Thomas G. Back'
_publ_contact_author
;
    Masood Parvez
    Department of Chemistry
    University of Calgary
    2500 University Drive N.W.
    Calgary, Alberta, Canada T2N 1N4  
;
_publ_contact_author_email       ' parvez@ucalgary.ca '
_publ_contact_author_fax         ' (403)289-9488 '
_publ_contact_author_phone       ' (403)220-5348 '
_publ_section_title
;
 Rearrangements and Intramolecular Diels-Alder Reactions of Normal and
 Vinylogous Aza-Morita-Baylis-Hillman Products Leading to Isoindoline
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3751
_journal_page_last               3760
_journal_paper_doi               10.1021/jo1005087
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H18 N2 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_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                 97.0650(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7942(3)
_cell_length_b                   11.7746(3)
_cell_length_c                   14.5883(4)
_cell_measurement_reflns_used    3810
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1840.06(9)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius APEX2 CCD'
_diffrn_measurement_method       ' ω and φ '
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7641
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.049
_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     235
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0457
_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)+(0.0378P)²+1.3660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3460
_reflns_number_total             4155
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1005087_si_005.cif
_cod_data_source_block           Compound_I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025461
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71071(5) 0.01540(4) 0.04904(3) 0.03075(13) Uani 1 1 d . . .
O1 O 0.76391(15) -0.04295(12) -0.02322(10) 0.0420(4) Uani 1 1 d . . .
O2 O 0.60693(13) -0.03160(11) 0.08793(9) 0.0379(3) Uani 1 1 d . . .
N1 N 0.82361(15) 0.02963(13) 0.13345(11) 0.0325(4) Uani 1 1 d . . .
N2 N 1.31999(17) 0.41623(16) 0.18117(14) 0.0453(4) Uani 1 1 d . . .
C1 C 1.01252(17) 0.11930(16) 0.19393(13) 0.0309(4) Uani 1 1 d . . .
H1 H 1.0444 0.0629 0.2425 0.037 Uiso 1 1 calc R . .
C2 C 1.11698(17) 0.19529(16) 0.17665(12) 0.0306(4) Uani 1 1 d . . .
H2 H 1.1831 0.1659 0.1463 0.037 Uiso 1 1 calc R . .
C3 C 1.12006(16) 0.30417(15) 0.20279(12) 0.0274(4) Uani 1 1 d . . .
C4 C 1.01838(17) 0.36566(15) 0.24694(12) 0.0272(4) Uani 1 1 d . . .
H4 H 1.0518 0.3835 0.3123 0.033 Uiso 1 1 calc R . .
C5 C 0.90532(17) 0.28999(16) 0.24813(12) 0.0298(4) Uani 1 1 d . . .
H5 H 0.8312 0.3223 0.2658 0.036 Uiso 1 1 calc R . .
C6 C 0.90452(17) 0.18137(16) 0.22579(12) 0.0296(4) Uani 1 1 d . . .
C7 C 0.79692(19) 0.09980(17) 0.21459(13) 0.0346(4) Uani 1 1 d . . .
H7A H 0.7954 0.0523 0.2704 0.042 Uiso 1 1 calc R . .
H7B H 0.7163 0.1403 0.2015 0.042 Uiso 1 1 calc R . .
C8 C 0.95090(19) 0.05455(18) 0.10936(14) 0.0371(4) Uani 1 1 d . . .
H8A H 0.9469 0.1018 0.0530 0.044 Uiso 1 1 calc R . .
H8B H 0.9968 -0.0164 0.0997 0.044 Uiso 1 1 calc R . .
C9 C 1.23019(18) 0.36838(16) 0.19035(13) 0.0322(4) Uani 1 1 d . . .
C10 C 0.98455(17) 0.47736(15) 0.19723(13) 0.0298(4) Uani 1 1 d . . .
C11 C 1.03018(18) 0.58010(16) 0.23458(14) 0.0347(4) Uani 1 1 d . . .
H11 H 1.0846 0.5804 0.2909 0.042 Uiso 1 1 calc R . .
C12 C 0.9971(2) 0.68207(18) 0.19050(17) 0.0449(5) Uani 1 1 d . . .
H12 H 1.0283 0.7516 0.2171 0.054 Uiso 1 1 calc R . .
C13 C 0.9191(2) 0.6828(2) 0.10815(18) 0.0508(6) Uani 1 1 d . . .
H13 H 0.8959 0.7526 0.0782 0.061 Uiso 1 1 calc R . .
C14 C 0.8750(2) 0.5809(2) 0.06957(16) 0.0504(6) Uani 1 1 d . . .
H14 H 0.8221 0.5809 0.0125 0.060 Uiso 1 1 calc R . .
C15 C 0.9073(2) 0.47888(18) 0.11354(14) 0.0400(5) Uani 1 1 d . . .
H15 H 0.8765 0.4095 0.0863 0.048 Uiso 1 1 calc R . .
C16 C 0.66796(18) 0.15329(16) 0.00960(12) 0.0306(4) Uani 1 1 d . . .
C17 C 0.73800(19) 0.21053(17) -0.04986(13) 0.0344(4) Uani 1 1 d . . .
H17 H 0.8074 0.1745 -0.0718 0.041 Uiso 1 1 calc R . .
C18 C 0.7055(2) 0.32055(18) -0.07672(14) 0.0396(5) Uani 1 1 d . . .
H18 H 0.7538 0.3608 -0.1162 0.047 Uiso 1 1 calc R . .
C19 C 0.6032(2) 0.37164(18) -0.04614(15) 0.0458(5) Uani 1 1 d . . .
H19 H 0.5811 0.4469 -0.0650 0.055 Uiso 1 1 calc R . .
C20 C 0.5324(2) 0.3142(2) 0.01178(17) 0.0507(6) Uani 1 1 d . . .
H20 H 0.4615 0.3497 0.0320 0.061 Uiso 1 1 calc R . .
C21 C 0.5651(2) 0.20471(18) 0.04039(15) 0.0405(5) Uani 1 1 d . . .
H21 H 0.5174 0.1653 0.0808 0.049 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.69(9) . . ?
O2 S1 N1 106.84(8) . . ?
O1 S1 N1 105.92(9) . . ?
O2 S1 C16 107.43(9) . . ?
O1 S1 C16 108.24(9) . . ?
N1 S1 C16 107.02(8) . . ?
C8 N1 C7 110.49(14) . . ?
C8 N1 S1 117.88(13) . . ?
C7 N1 S1 117.01(13) . . ?
C2 C1 C6 113.26(15) . . ?
C2 C1 C8 115.27(16) . . ?
C6 C1 C8 102.44(15) . . ?
C2 C1 H1 108.5 . . ?
C6 C1 H1 108.5 . . ?
C8 C1 H1 108.5 . . ?
C3 C2 C1 121.48(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C9 117.38(17) . . ?
C2 C3 C4 125.66(17) . . ?
C9 C3 C4 116.95(15) . . ?
C5 C4 C3 110.44(14) . . ?
C5 C4 C10 111.54(15) . . ?
C3 C4 C10 110.62(14) . . ?
C5 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C10 C4 H4 108.0 . . ?
C6 C5 C4 123.28(17) . . ?
C6 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C6 C1 124.61(17) . . ?
C5 C6 C7 128.96(18) . . ?
C1 C6 C7 105.99(15) . . ?
N1 C7 C6 102.55(14) . . ?
N1 C7 H7A 111.3 . . ?
C6 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N1 C8 C1 103.30(15) . . ?
N1 C8 H8A 111.1 . . ?
C1 C8 H8A 111.1 . . ?
N1 C8 H8B 111.1 . . ?
C1 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C3 177.7(2) . . ?
C15 C10 C11 118.51(18) . . ?
C15 C10 C4 120.74(17) . . ?
C11 C10 C4 120.74(17) . . ?
C12 C11 C10 120.81(19) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C21 C16 C17 120.53(18) . . ?
C21 C16 S1 118.92(14) . . ?
C17 C16 S1 120.54(15) . . ?
C18 C17 C16 119.37(19) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 120.08(19) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.49(19) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
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
S1 O2 1.4280(14) . ?
S1 O1 1.4359(14) . ?
S1 N1 1.6311(16) . ?
S1 C16 1.7649(19) . ?
N1 C8 1.489(2) . ?
N1 C7 1.500(2) . ?
N2 C9 1.143(3) . ?
C1 C2 1.485(3) . ?
C1 C6 1.497(2) . ?
C1 C8 1.531(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.337(3) . ?
C2 H2 0.9500 . ?
C3 C9 1.439(3) . ?
C3 C4 1.522(2) . ?
C4 C5 1.513(2) . ?
C4 C10 1.524(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.320(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C15 1.391(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.387(3) . ?
C16 C17 1.393(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 167.69(14) . . . . ?
O1 S1 N1 C8 37.84(16) . . . . ?
C16 S1 N1 C8 -77.48(15) . . . . ?
O2 S1 N1 C7 -56.74(15) . . . . ?
O1 S1 N1 C7 173.41(13) . . . . ?
C16 S1 N1 C7 58.10(15) . . . . ?
C6 C1 C2 C3 10.7(2) . . . . ?
C8 C1 C2 C3 128.27(19) . . . . ?
C1 C2 C3 C9 174.70(16) . . . . ?
C1 C2 C3 C4 -3.7(3) . . . . ?
C2 C3 C4 C5 -6.2(2) . . . . ?
C9 C3 C4 C5 175.46(15) . . . . ?
C2 C3 C4 C10 -130.15(19) . . . . ?
C9 C3 C4 C10 51.5(2) . . . . ?
C3 C4 C5 C6 8.8(2) . . . . ?
C10 C4 C5 C6 132.30(18) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
C4 C5 C6 C7 -173.13(17) . . . . ?
C2 C1 C6 C5 -8.2(3) . . . . ?
C8 C1 C6 C5 -133.02(19) . . . . ?
C2 C1 C6 C7 164.75(15) . . . . ?
C8 C1 C6 C7 39.95(18) . . . . ?
C8 N1 C7 C6 9.8(2) . . . . ?
S1 N1 C7 C6 -128.87(14) . . . . ?
C5 C6 C7 N1 141.74(19) . . . . ?
C1 C6 C7 N1 -30.82(18) . . . . ?
C7 N1 C8 C1 14.1(2) . . . . ?
S1 N1 C8 C1 152.37(13) . . . . ?
C2 C1 C8 N1 -155.80(16) . . . . ?
C6 C1 C8 N1 -32.33(19) . . . . ?
C5 C4 C10 C15 -44.8(2) . . . . ?
C3 C4 C10 C15 78.5(2) . . . . ?
C5 C4 C10 C11 135.16(17) . . . . ?
C3 C4 C10 C11 -101.49(19) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C4 C10 C11 C12 -178.48(18) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C11 C10 C15 C14 -1.2(3) . . . . ?
C4 C10 C15 C14 178.76(19) . . . . ?
O2 S1 C16 C21 16.01(18) . . . . ?
O1 S1 C16 C21 147.82(16) . . . . ?
N1 S1 C16 C21 -98.42(17) . . . . ?
O2 S1 C16 C17 -165.40(15) . . . . ?
O1 S1 C16 C17 -33.59(18) . . . . ?
N1 S1 C16 C17 80.17(17) . . . . ?
C21 C16 C17 C18 1.3(3) . . . . ?
S1 C16 C17 C18 -177.31(15) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C17 C16 C21 C20 -0.2(3) . . . . ?
S1 C16 C21 C20 178.35(18) . . . . ?
C19 C20 C21 C16 -0.7(4) . . . . ?
