#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/79/1517961.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_1517961
loop_
_publ_author_name
'Engl, Oliver D.'
'Fritz, Sven P.'
'Käslin, Alexander'
'Wennemers, Helma'
_publ_section_title
;
 Organocatalytic route to dihydrocoumarins and dihydroquinolinones in all
 stereochemical configurations.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5454
_journal_page_last               5457
_journal_paper_doi               10.1021/ol502697s
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O6 S'
_chemical_formula_sum            'C19 H17 N O6 S'
_chemical_formula_weight         387.39
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.281(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.1913(12)
_cell_length_b                   6.4335(3)
_cell_length_c                   11.2245(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.45
_cell_volume                     1746.49(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21694
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_min         1.684
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0503 before and 0.0414 after correction.
The Ratio of minimum to maximum transmission is 0.9262.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       rod
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.018(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4059
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+0.5497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.834
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3875
_reflns_number_total             4059
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol502697s_si_002.cif
_cod_data_source_block           w091113_0m
_cod_depositor_comments          'Adding full bibliography for 1517961.cif.'
_cod_database_code               1517961
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
S1 S 0.51004(2) 0.55254(8) 0.17980(4) 0.02125(12) Uani 1 1 d . .
O1 O 0.37267(7) -0.1159(2) 0.37439(13) 0.0259(3) Uani 1 1 d . .
O2 O 0.76688(6) 0.6488(2) 0.50591(13) 0.0274(4) Uani 1 1 d . .
O3 O 0.77620(6) 0.7633(3) 0.32702(14) 0.0293(4) Uani 1 1 d . .
O4 O 0.58123(6) 0.4531(2) 0.35250(12) 0.0220(3) Uani 1 1 d . .
O5 O 0.62665(6) 0.6869(2) 0.02636(11) 0.0200(3) Uani 1 1 d . .
O6 O 0.57551(6) 0.9559(2) 0.07220(13) 0.0248(3) Uani 1 1 d . .
N1 N 0.74868(7) 0.6931(3) 0.40686(15) 0.0213(4) Uani 1 1 d . .
C1 C 0.35315(9) -0.2747(3) 0.29639(18) 0.0226(4) Uani 1 1 d . .
H1A H 0.3336 -0.2117 0.2281 0.034 Uiso 1 1 calc R U
H1B H 0.3279 -0.3660 0.3390 0.034 Uiso 1 1 calc R U
H1C H 0.3845 -0.3560 0.2683 0.034 Uiso 1 1 calc R U
C2 C 0.40611(8) 0.0310(3) 0.32618(17) 0.0189(4) Uani 1 1 d . .
C3 C 0.42410(8) 0.0250(3) 0.21039(17) 0.0181(4) Uani 1 1 d . .
H3 H 0.4134 -0.0863 0.1592 0.022 Uiso 1 1 calc R U
C4 C 0.45785(8) 0.1819(3) 0.16922(17) 0.0193(4) Uani 1 1 d . .
H4 H 0.4705 0.1773 0.0897 0.023 Uiso 1 1 calc R U
C5 C 0.47332(8) 0.3452(3) 0.24265(18) 0.0182(4) Uani 1 1 d . .
C6 C 0.57060(7) 0.5651(3) 0.27008(16) 0.0156(4) Uani 1 1 d . .
C7 C 0.60806(8) 0.7499(3) 0.23926(17) 0.0157(4) Uani 1 1 d . .
C8 C 0.66974(8) 0.6905(3) 0.25766(16) 0.0159(4) Uani 1 1 d . .
H8 H 0.6917 0.8104 0.2275 0.019 Uiso 1 1 calc R U
C9 C 0.68173(8) 0.5097(3) 0.17725(16) 0.0156(4) Uani 1 1 d . .
C10 C 0.71428(8) 0.3391(3) 0.20657(18) 0.0186(4) Uani 1 1 d . .
H10 H 0.7304 0.3286 0.2843 0.022 Uiso 1 1 calc R U
C11 C 0.72359(8) 0.1834(3) 0.12357(18) 0.0213(4) Uani 1 1 d . .
H11 H 0.7465 0.0685 0.1443 0.026 Uiso 1 1 calc R U
C12 C 0.69956(8) 0.1954(3) 0.01098(18) 0.0229(4) Uani 1 1 d . .
H12 H 0.7062 0.0890 -0.0457 0.027 Uiso 1 1 calc R U
C13 C 0.68726(8) 0.6606(3) 0.38714(17) 0.0179(4) Uani 1 1 d . .
H13A H 0.6668 0.7599 0.4371 0.021 Uiso 1 1 calc R U
H13B H 0.6774 0.5182 0.4125 0.021 Uiso 1 1 calc R U
C14 C 0.59021(9) 0.9343(3) 0.31537(19) 0.0216(4) Uani 1 1 d . .
H14A H 0.6166 1.0485 0.3067 0.032 Uiso 1 1 calc R U
H14B H 0.5892 0.8919 0.3992 0.032 Uiso 1 1 calc R U
H14C H 0.5533 0.9807 0.2890 0.032 Uiso 1 1 calc R U
C15 C 0.42184(9) 0.1951(3) 0.40051(18) 0.0249(4) Uani 1 1 d . .
H15 H 0.4096 0.1987 0.4803 0.030 Uiso 1 1 calc R U
C16 C 0.45477(9) 0.3511(3) 0.35915(18) 0.0239(4) Uani 1 1 d . .
H16 H 0.4650 0.4634 0.4100 0.029 Uiso 1 1 calc R U
C17 C 0.60102(8) 0.8095(3) 0.10802(17) 0.0180(4) Uani 1 1 d . .
C18 C 0.65796(8) 0.5159(3) 0.06328(17) 0.0172(4) Uani 1 1 d . .
C19 C 0.66599(8) 0.3615(3) -0.01943(18) 0.0209(4) Uani 1 1 d . .
H19 H 0.6487 0.3690 -0.0961 0.025 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
C5 S1 C6 102.98(9)
C2 O1 C1 116.49(15)
C17 O5 C18 120.47(15)
O2 N1 C13 115.75(17)
O3 N1 O2 124.49(17)
O3 N1 C13 119.75(16)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C3 123.81(18)
O1 C2 C15 116.35(17)
C3 C2 C15 119.84(19)
C2 C3 H3 120.2
C2 C3 C4 119.64(18)
C4 C3 H3 120.2
C3 C4 H4 119.7
C5 C4 C3 120.61(18)
C5 C4 H4 119.7
C4 C5 S1 118.02(15)
C4 C5 C16 119.49(19)
C16 C5 S1 122.15(16)
O4 C6 S1 125.31(16)
O4 C6 C7 121.45(16)
C7 C6 S1 113.07(13)
C6 C7 C8 110.47(15)
C14 C7 C6 107.38(15)
C14 C7 C8 113.55(16)
C17 C7 C6 110.92(15)
C17 C7 C8 106.05(15)
C17 C7 C14 108.49(16)
C7 C8 H8 106.4
C9 C8 C7 107.98(15)
C9 C8 H8 106.4
C9 C8 C13 115.03(16)
C13 C8 C7 113.98(15)
C13 C8 H8 106.4
C10 C9 C8 125.86(17)
C10 C9 C18 117.53(17)
C18 C9 C8 116.61(16)
C9 C10 H10 119.6
C9 C10 C11 120.75(19)
C11 C10 H10 119.6
C10 C11 H11 119.9
C12 C11 C10 120.12(19)
C12 C11 H11 119.9
C11 C12 H12 119.9
C19 C12 C11 120.2(2)
C19 C12 H12 119.9
N1 C13 C8 112.04(16)
N1 C13 H13A 109.2
N1 C13 H13B 109.2
C8 C13 H13A 109.2
C8 C13 H13B 109.2
H13A C13 H13B 107.9
C7 C14 H14A 109.5
C7 C14 H14B 109.5
C7 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C2 C15 H15 119.8
C16 C15 C2 120.38(19)
C16 C15 H15 119.8
C5 C16 H16 120.0
C15 C16 C5 120.0(2)
C15 C16 H16 120.0
O5 C17 C7 117.33(16)
O6 C17 O5 117.95(18)
O6 C17 C7 124.72(18)
C9 C18 O5 120.46(17)
C19 C18 O5 116.96(17)
C19 C18 C9 122.51(18)
C12 C19 H19 120.6
C18 C19 C12 118.89(19)
C18 C19 H19 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.759(2)
S1 C6 1.7645(18)
O1 C1 1.419(2)
O1 C2 1.364(2)
O2 N1 1.220(2)
O3 N1 1.215(2)
O4 C6 1.196(2)
O5 C17 1.368(2)
O5 C18 1.393(2)
O6 C17 1.191(2)
N1 C13 1.512(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.380(3)
C2 C15 1.393(3)
C3 H3 0.9500
C3 C4 1.384(3)
C4 H4 0.9500
C4 C5 1.382(3)
C5 C16 1.392(3)
C6 C7 1.539(3)
C7 C8 1.550(3)
C7 C14 1.530(3)
C7 C17 1.528(3)
C8 H8 1.0000
C8 C9 1.505(3)
C8 C13 1.517(3)
C9 C10 1.386(3)
C9 C18 1.391(3)
C10 H10 0.9500
C10 C11 1.390(3)
C11 H11 0.9500
C11 C12 1.381(3)
C12 H12 0.9500
C12 C19 1.380(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15 0.9500
C15 C16 1.369(3)
C16 H16 0.9500
C18 C19 1.377(3)
C19 H19 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
S1 C5 C16 C15 173.71(17)
S1 C6 C7 C8 -145.79(13)
S1 C6 C7 C14 89.89(16)
S1 C6 C7 C17 -28.50(19)
O1 C2 C3 C4 179.76(18)
O1 C2 C15 C16 -179.1(2)
O2 N1 C13 C8 -172.00(17)
O3 N1 C13 C8 9.4(3)
O4 C6 C7 C8 38.7(2)
O4 C6 C7 C14 -85.6(2)
O4 C6 C7 C17 155.98(18)
O5 C18 C19 C12 176.04(17)
C1 O1 C2 C3 -4.2(3)
C1 O1 C2 C15 175.37(18)
C2 C3 C4 C5 -0.5(3)
C2 C15 C16 C5 -0.8(3)
C3 C2 C15 C16 0.4(3)
C3 C4 C5 S1 -173.33(15)
C3 C4 C5 C16 0.1(3)
C4 C5 C16 C15 0.5(3)
C5 S1 C6 O4 0.3(2)
C5 S1 C6 C7 -175.04(13)
C6 S1 C5 C4 -124.10(16)
C6 S1 C5 C16 62.63(19)
C6 C7 C8 C9 59.82(19)
C6 C7 C8 C13 -69.3(2)
C6 C7 C17 O5 -77.4(2)
C6 C7 C17 O6 103.6(2)
C7 C8 C9 C10 -139.51(19)
C7 C8 C9 C18 40.7(2)
C7 C8 C13 N1 -155.90(16)
C8 C7 C17 O5 42.5(2)
C8 C7 C17 O6 -136.5(2)
C8 C9 C10 C11 -178.34(18)
C8 C9 C18 O5 2.5(2)
C8 C9 C18 C19 179.42(18)
C9 C8 C13 N1 78.6(2)
C9 C10 C11 C12 -1.1(3)
C9 C18 C19 C12 -1.0(3)
C10 C9 C18 O5 -177.34(17)
C10 C9 C18 C19 -0.4(3)
C10 C11 C12 C19 -0.3(3)
C11 C12 C19 C18 1.4(3)
C13 C8 C9 C10 -11.0(3)
C13 C8 C9 C18 169.23(16)
C14 C7 C8 C9 -179.48(16)
C14 C7 C8 C13 51.4(2)
C14 C7 C17 O5 164.85(17)
C14 C7 C17 O6 -14.1(3)
C15 C2 C3 C4 0.2(3)
C17 O5 C18 C9 -25.2(3)
C17 O5 C18 C19 157.71(17)
C17 C7 C8 C9 -60.45(19)
C17 C7 C8 C13 170.42(16)
C18 O5 C17 O6 178.75(17)
C18 O5 C17 C7 -0.3(2)
C18 C9 C10 C11 1.5(3)
