#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/42/1504224.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_1504224
loop_
_publ_author_name
'Webster, Robert'
'Lautens, Mark'
_publ_section_title
;
 Conformational effects in diastereoselective aryne Diels-Alder reactions:
 synthesis of benzo-fused [2.2.1] heterobicycles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4688
_journal_page_last               4691
_journal_paper_doi               10.1021/ol9019869
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N O4 S'
_chemical_formula_sum            'C15 H19 N O4 S'
_chemical_formula_weight         309.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.7128(17)
_cell_length_b                   8.0293(5)
_cell_length_c                   8.0067(5)
_cell_measurement_reflns_used    7017
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     1460.16(17)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0935
_diffrn_reflns_av_sigmaI/netI    0.1194
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7017
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.26(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0591
_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)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                1535
_reflns_number_total             2573
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol9019869_si_003.cif
_cod_data_source_block           k0832
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1504224
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.31467(6) 0.56972(15) 0.24956(17) 0.0328(4) Uani 1 1 d .
O1 O 0.30336(18) 0.0381(4) 0.3674(4) 0.0419(11) Uani 1 1 d .
O2 O 0.34120(18) 0.1478(4) 0.0645(5) 0.0408(11) Uani 1 1 d .
O3 O 0.25427(15) 0.5191(4) 0.2627(5) 0.0427(10) Uani 1 1 d .
O4 O 0.34394(19) 0.6232(4) 0.3990(5) 0.0449(11) Uani 1 1 d .
N1 N 0.35383(19) 0.4135(5) 0.1564(5) 0.0288(11) Uani 1 1 d .
C1 C 0.3015(3) 0.0034(7) 0.5334(7) 0.0377(15) Uani 1 1 d .
H1A H 0.2860 -0.0966 0.5791 0.045 Uiso 1 1 calc R
C2 C 0.3242(3) 0.1279(6) 0.6244(7) 0.0426(16) Uani 1 1 d .
H2A H 0.3275 0.1334 0.7425 0.051 Uiso 1 1 calc R
C3 C 0.3423(3) 0.2503(7) 0.5060(7) 0.0382(15) Uani 1 1 d .
H3A H 0.3606 0.3539 0.5303 0.046 Uiso 1 1 calc R
C4 C 0.3286(3) 0.1920(6) 0.3547(7) 0.0318(15) Uani 1 1 d .
C5 C 0.3400(3) 0.2451(6) 0.1819(7) 0.0328(14) Uani 1 1 d .
C6 C 0.3733(3) 0.4608(5) -0.0157(6) 0.0285(13) Uani 1 1 d .
H6A H 0.3441 0.4199 -0.0999 0.034 Uiso 1 1 calc R
C7 C 0.4355(2) 0.4051(6) -0.0643(7) 0.0366(14) Uani 1 1 d .
H7A H 0.4347 0.3263 -0.1593 0.044 Uiso 1 1 calc R
H7B H 0.4561 0.3525 0.0310 0.044 Uiso 1 1 calc R
C8 C 0.4651(3) 0.5725(7) -0.1143(6) 0.0342(14) Uani 1 1 d .
H8A H 0.5090 0.5673 -0.1228 0.041 Uiso 1 1 calc R
C9 C 0.4346(2) 0.6377(7) -0.2707(7) 0.0375(14) Uani 1 1 d .
H9A H 0.4299 0.5483 -0.3548 0.045 Uiso 1 1 calc R
H9B H 0.4571 0.7307 -0.3209 0.045 Uiso 1 1 calc R
C10 C 0.3738(2) 0.6981(6) -0.2066(6) 0.0334(14) Uani 1 1 d .
H10A H 0.3691 0.8196 -0.2224 0.040 Uiso 1 1 calc R
H10B H 0.3413 0.6394 -0.2640 0.040 Uiso 1 1 calc R
C11 C 0.3761(2) 0.6524(6) -0.0193(6) 0.0268(13) Uani 1 1 d .
C12 C 0.3252(3) 0.7176(6) 0.0847(7) 0.0369(14) Uani 1 1 d .
H12A H 0.2892 0.7270 0.0159 0.044 Uiso 1 1 calc R
H12B H 0.3347 0.8287 0.1311 0.044 Uiso 1 1 calc R
C13 C 0.4418(3) 0.6919(6) 0.0239(7) 0.0346(14) Uani 1 1 d .
C15 C 0.4635(3) 0.6469(8) 0.2002(7) 0.0435(16) Uani 1 1 d .
H15A H 0.4464 0.7243 0.2815 0.065 Uiso 1 1 calc R
H15B H 0.5066 0.6550 0.2042 0.065 Uiso 1 1 calc R
H15C H 0.4514 0.5329 0.2274 0.065 Uiso 1 1 calc R
C16 C 0.4578(3) 0.8737(7) -0.0037(7) 0.0451(16) Uani 1 1 d .
H16A H 0.4404 0.9416 0.0853 0.068 Uiso 1 1 calc R
H16B H 0.4425 0.9104 -0.1120 0.068 Uiso 1 1 calc R
H16C H 0.5007 0.8862 -0.0021 0.068 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
O3 S1 O4 117.8(2)
O3 S1 N1 108.8(2)
O4 S1 N1 110.0(2)
O3 S1 C12 111.7(3)
O4 S1 C12 110.8(2)
N1 S1 C12 95.5(2)
C1 O1 C4 105.8(4)
C5 N1 C6 116.4(4)
C5 N1 S1 121.8(4)
C6 N1 S1 111.7(3)
C2 C1 O1 111.5(5)
C1 C2 C3 105.3(5)
C4 C3 C2 107.1(5)
C3 C4 O1 110.3(5)
C3 C4 C5 135.4(5)
O1 C4 C5 113.9(5)
O2 C5 N1 119.9(5)
O2 C5 C4 122.8(5)
N1 C5 C4 117.1(4)
N1 C6 C7 115.6(4)
N1 C6 C11 106.4(4)
C7 C6 C11 104.4(4)
C6 C7 C8 102.2(4)
C9 C8 C7 108.2(5)
C9 C8 C13 102.6(4)
C7 C8 C13 101.7(4)
C8 C9 C10 103.9(4)
C11 C10 C9 102.6(4)
C12 C11 C6 107.6(4)
C12 C11 C10 115.2(4)
C6 C11 C10 104.7(4)
C12 C11 C13 122.4(4)
C6 C11 C13 103.8(4)
C10 C11 C13 101.4(4)
C11 C12 S1 106.1(3)
C16 C13 C15 106.4(5)
C16 C13 C8 114.0(4)
C15 C13 C8 113.5(5)
C16 C13 C11 113.0(4)
C15 C13 C11 117.4(5)
C8 C13 C11 92.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.435(4)
S1 O4 1.435(4)
S1 N1 1.709(4)
S1 C12 1.791(5)
O1 C1 1.358(6)
O1 C4 1.366(6)
O2 C5 1.223(6)
N1 C5 1.404(7)
N1 C6 1.495(6)
C1 C2 1.341(7)
C2 C3 1.426(7)
C3 C4 1.335(7)
C4 C5 1.471(7)
C6 C7 1.533(8)
C6 C11 1.540(6)
C7 C8 1.555(7)
C8 C9 1.524(8)
C8 C13 1.557(7)
C9 C10 1.550(7)
C10 C11 1.545(7)
C11 C12 1.517(7)
C11 C13 1.566(8)
C13 C16 1.520(7)
C13 C15 1.539(8)
