#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/39/1513909.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_1513909
loop_
_publ_author_name
'Arai, Takayoshi'
'Yamamoto, Yushi'
_publ_section_title
;
 Diversity-Oriented Asymmetric Catalysis (DOAC): Stereochemically
 Divergent Synthesis of Thiochromanes Using an
 Imidazoline-Aminophenol-Nickel-Catalyzed Michael/Henry Reaction.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1700
_journal_page_last               1703
_journal_paper_doi               10.1021/ol500361w
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H13 N O3 S'
_chemical_formula_weight         287.32
_chemical_name_common            arai39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0289(12)
_cell_length_b                   11.1264(13)
_cell_length_c                   24.230(3)
_cell_measurement_temperature    173.(2)
_cell_volume                     2703.7(6)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite '
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15425
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.339
_refine_ls_abs_structure_details
;
Flack x determined using 1884 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          3.365
_refine_ls_shift/su_mean         0.276
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                5169
_reflns_number_total             6102
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol500361w_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        2703.7(5)
_cod_database_code               1513909
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
S S1 0.45781(9) 0.16225(9) 0.09497(4) 0.0320(2) Uani d . . 1
S S2 0.72052(9) 0.52639(9) 0.19638(4) 0.0356(2) Uani d . . 1
C C1 0.5515(3) 0.0123(3) 0.01036(13) 0.0236(7) Uani d . . 1
C C2 0.5794(3) 0.0939(3) 0.05288(14) 0.0267(7) Uani d . . 1
C C3 0.7117(4) 0.1268(3) 0.06351(15) 0.0285(8) Uani d . . 1
C C4 0.8147(4) 0.0789(4) 0.03321(16) 0.0326(8) Uani d . . 1
C C5 0.7882(4) -0.0043(3) -0.00807(16) 0.0333(9) Uani d . . 1
C C6 0.6582(4) -0.0363(3) -0.01908(15) 0.0299(8) Uani d . . 1
C C7 0.4118(4) -0.0276(3) -0.00489(14) 0.0252(7) Uani d . . 1
C C8 0.3075(3) 0.0629(3) 0.01579(13) 0.0236(7) Uani d . . 1
C C9 0.3103(3) 0.0741(3) 0.07868(13) 0.0247(7) Uani d . . 1
C C10 0.1920(3) 0.1352(3) 0.10485(13) 0.0232(7) Uani d . . 1
C C11 0.1324(4) 0.0836(3) 0.15064(14) 0.0299(8) Uani d . . 1
C C12 0.0228(4) 0.1380(3) 0.17515(17) 0.0352(9) Uani d . . 1
C C13 -0.0279(4) 0.2436(4) 0.15469(16) 0.0332(8) Uani d . . 1
C C14 0.0315(4) 0.2955(4) 0.10938(16) 0.0342(9) Uani d . . 1
C C15 0.1406(4) 0.2427(3) 0.08426(14) 0.0302(8) Uani d . . 1
C C16 0.8141(3) 0.7209(3) 0.13349(14) 0.0245(7) Uani d . . 1
C C17 0.8410(3) 0.6191(3) 0.16528(14) 0.0265(8) Uani d . . 1
C C18 0.9736(4) 0.5891(3) 0.17709(15) 0.0303(8) Uani d . . 1
C C19 1.0776(4) 0.6593(4) 0.15841(15) 0.0335(8) Uani d . . 1
C C20 1.0511(4) 0.7603(4) 0.12641(16) 0.0337(9) Uani d . . 1
C C21 0.9202(4) 0.7892(3) 0.11424(15) 0.0294(8) Uani d . . 1
C C22 0.6742(4) 0.7583(3) 0.11734(15) 0.0247(7) Uani d . . 1
C C23 0.5725(3) 0.7133(3) 0.16023(14) 0.0235(7) Uani d . . 1
C C24 0.5668(4) 0.5770(3) 0.16449(15) 0.0240(7) Uani d . . 1
C C25 0.4536(3) 0.5284(3) 0.19920(13) 0.0230(6) Uani d . . 1
C C26 0.3798(4) 0.4329(3) 0.17978(16) 0.0311(8) Uani d . . 1
C C27 0.2759(4) 0.3853(4) 0.21087(16) 0.0349(9) Uani d . . 1
C C28 0.2444(4) 0.4350(4) 0.26103(16) 0.0349(9) Uani d . . 1
C C29 0.3180(4) 0.5307(4) 0.28095(15) 0.0380(9) Uani d . . 1
C C30 0.4231(4) 0.5768(4) 0.25059(14) 0.0334(8) Uani d . . 1
N N1 0.1719(3) 0.0236(3) -0.00319(12) 0.0286(7) Uani d . . 1
N N2 0.4366(3) 0.7593(3) 0.14359(13) 0.0311(7) Uani d . . 1
O O1 0.3928(3) -0.1447(2) 0.01723(12) 0.0330(6) Uani d . . 1
O O2 0.1296(3) 0.0674(2) -0.04601(11) 0.0421(7) Uani d . . 1
O O3 0.1115(3) -0.0501(2) 0.02475(11) 0.0375(6) Uani d . . 1
O O4 0.6500(3) 0.7120(2) 0.06355(9) 0.0297(6) Uani d . . 1
H H4A 0.5729 0.7313 0.0534 0.045 Uiso calc U R 1
O O5 0.3718(3) 0.7009(3) 0.11067(11) 0.0401(7) Uani d . . 1
O O6 0.3999(3) 0.8544(3) 0.16390(14) 0.0529(8) Uani d . . 1
H H1 0.730(5) 0.180(4) 0.0938(19) 0.037(14) Uiso d . . 1
H H2 0.909(4) 0.096(3) 0.0434(15) 0.021(10) Uiso d . . 1
H H3 0.857(5) -0.033(4) -0.0258(18) 0.042(12) Uiso d . . 1
H H4 0.640(4) -0.092(4) -0.0474(17) 0.038(12) Uiso d . . 1
H H5 0.403(4) -0.028(3) -0.0435(16) 0.022(10) Uiso d . . 1
H H6 0.322(3) 0.140(3) -0.0028(14) 0.020(9) Uiso d . . 1
H H7 0.321(4) -0.003(3) 0.0932(14) 0.013(9) Uiso d . . 1
H H8 0.173(5) 0.014(4) 0.1671(18) 0.042(12) Uiso d . . 1
H H9 -0.014(5) 0.105(4) 0.205(2) 0.041(14) Uiso d . . 1
H H10 -0.107(5) 0.276(4) 0.1708(18) 0.036(13) Uiso d . . 1
H H11 0.000(6) 0.359(6) 0.097(2) 0.05(2) Uiso d . . 1
H H12 0.181(4) 0.275(4) 0.0553(18) 0.036(12) Uiso d . . 1
H H13 0.337(6) -0.171(5) 0.001(2) 0.061(19) Uiso d . . 1
H H21 0.401(8) 0.390(7) 0.148(3) 0.10(3) Uiso d . . 1
H H22 0.224(4) 0.319(4) 0.1988(16) 0.039(12) Uiso d . . 1
H H23 0.170(5) 0.403(5) 0.285(2) 0.066(16) Uiso d . . 1
H H24 0.300(5) 0.563(4) 0.3183(19) 0.048(13) Uiso d . . 1
H H25 0.482(5) 0.639(4) 0.2663(18) 0.061(13) Uiso d . . 1
H H14 0.987(5) 0.517(5) 0.199(2) 0.049(15) Uiso d . . 1
H H15 1.173(5) 0.641(4) 0.1690(18) 0.046(13) Uiso d . . 1
H H16 1.127(5) 0.815(5) 0.1099(19) 0.048(15) Uiso d . . 1
H H17 0.904(6) 0.869(5) 0.093(2) 0.040(17) Uiso d . . 1
H H18 0.669(4) 0.849(4) 0.1169(15) 0.017(10) Uiso d . . 1
H H19 0.583(4) 0.752(3) 0.1973(16) 0.022(11) Uiso d . . 1
H H20 0.559(5) 0.547(5) 0.133(2) 0.052(18) Uiso d . . 1
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
C2 S1 C9 101.79(16)
C17 S2 C24 102.67(16)
C6 C1 C2 118.3(3)
C6 C1 C7 118.1(3)
C2 C1 C7 123.6(3)
C3 C2 C1 119.6(3)
C3 C2 S1 115.9(3)
C1 C2 S1 124.5(3)
C4 C3 C2 120.8(3)
C4 C3 H1 120.(3)
C2 C3 H1 119.(3)
C3 C4 C5 120.0(4)
C3 C4 H2 120.(2)
C5 C4 H2 119.(2)
C6 C5 C4 119.5(4)
C6 C5 H3 124.(3)
C4 C5 H3 117.(3)
C5 C6 C1 121.8(4)
C5 C6 H4 120.(3)
C1 C6 H4 118.(3)
O1 C7 C1 107.5(3)
O1 C7 C8 112.7(3)
C1 C7 C8 111.0(3)
O1 C7 H5 111.(2)
C1 C7 H5 109.(2)
C8 C7 H5 105.(2)
N1 C8 C9 110.2(3)
N1 C8 C7 109.0(3)
C9 C8 C7 111.4(3)
N1 C8 H6 105.(2)
C9 C8 H6 112.7(19)
C7 C8 H6 109.(2)
C10 C9 C8 116.2(3)
C10 C9 S1 107.8(2)
C8 C9 S1 106.0(2)
C10 C9 H7 110.(2)
C8 C9 H7 108.(2)
S1 C9 H7 109.(2)
C11 C10 C15 118.8(3)
C11 C10 C9 119.3(3)
C15 C10 C9 121.8(3)
C10 C11 C12 120.2(4)
C10 C11 H8 119.(3)
C12 C11 H8 121.(3)
C13 C12 C11 120.8(4)
C13 C12 H9 119.(3)
C11 C12 H9 120.(3)
C12 C13 C14 119.1(4)
C12 C13 H10 119.(3)
C14 C13 H10 122.(3)
C13 C14 C15 121.0(4)
C13 C14 H11 118.(4)
C15 C14 H11 121.(4)
C14 C15 C10 120.0(4)
C14 C15 H12 123.(3)
C10 C15 H12 117.(3)
C21 C16 C17 118.8(3)
C21 C16 C22 118.2(3)
C17 C16 C22 122.9(3)
C16 C17 C18 119.2(3)
C16 C17 S2 125.5(3)
C18 C17 S2 115.2(3)
C19 C18 C17 121.1(3)
C19 C18 H14 123.(3)
C17 C18 H14 116.(3)
C18 C19 C20 119.7(4)
C18 C19 H15 121.(3)
C20 C19 H15 119.(3)
C21 C20 C19 119.2(4)
C21 C20 H16 118.(3)
C19 C20 H16 123.(3)
C20 C21 C16 121.9(4)
C20 C21 H17 117.(3)
C16 C21 H17 121.(3)
O4 C22 C16 107.2(3)
O4 C22 C23 112.8(3)
C16 C22 C23 110.5(3)
O4 C22 H18 110.(2)
C16 C22 H18 109.(2)
C23 C22 H18 107.(2)
N2 C23 C24 108.8(3)
N2 C23 C22 107.9(3)
C24 C23 C22 113.3(3)
N2 C23 H19 101.(2)
C24 C23 H19 112.(2)
C22 C23 H19 113.(2)
C25 C24 C23 115.0(3)
C25 C24 S2 106.9(2)
C23 C24 S2 107.8(2)
C25 C24 H20 107.(4)
C23 C24 H20 110.(4)
S2 C24 H20 110.(4)
C26 C25 C30 119.1(3)
C26 C25 C24 119.3(3)
C30 C25 C24 121.6(3)
C25 C26 C27 120.7(4)
C25 C26 H21 124.(5)
C27 C26 H21 115.(5)
C28 C27 C26 119.9(4)
C28 C27 H22 117.(3)
C26 C27 H22 123.(3)
C27 C28 C29 119.8(4)
C27 C28 H23 123.(3)
C29 C28 H23 117.(3)
C28 C29 C30 120.4(4)
C28 C29 H24 120.(3)
C30 C29 H24 120.(3)
C29 C30 C25 120.0(4)
C29 C30 H25 121.(3)
C25 C30 H25 119.(3)
O2 N1 O3 124.4(3)
O2 N1 C8 117.3(3)
O3 N1 C8 118.3(3)
O5 N2 O6 124.4(3)
O5 N2 C23 118.4(3)
O6 N2 C23 117.2(3)
C7 O1 H13 105.(4)
C22 O4 H4A 109.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.762(4)
S1 C9 1.818(4)
S2 C17 1.758(4)
S2 C24 1.814(4)
C1 C6 1.395(5)
C1 C2 1.402(5)
C1 C7 1.515(5)
C2 C3 1.400(5)
C3 C4 1.375(5)
C3 H1 0.96(5)
C4 C5 1.388(5)
C4 H2 0.99(4)
C5 C6 1.378(5)
C5 H3 0.88(5)
C6 H4 0.94(4)
C7 O1 1.422(4)
C7 C8 1.536(5)
C7 H5 0.94(4)
C8 N1 1.501(4)
C8 C9 1.529(5)
C8 H6 0.98(4)
C9 C10 1.508(5)
C9 H7 0.93(4)
C10 C11 1.385(5)
C10 C15 1.395(5)
C11 C12 1.388(5)
C11 H8 0.96(4)
C12 C13 1.372(6)
C12 H9 0.90(5)
C13 C14 1.377(6)
C13 H10 0.95(5)
C14 C15 1.382(5)
C14 H11 0.83(6)
C15 H12 0.89(4)
C16 C21 1.388(5)
C16 C17 1.396(5)
C16 C22 1.515(5)
C17 C18 1.401(5)
C18 C19 1.378(5)
C18 H14 0.97(5)
C19 C20 1.391(6)
C19 H15 1.01(5)
C20 C21 1.384(6)
C20 H16 1.05(5)
C21 H17 1.03(6)
C22 O4 1.423(4)
C22 C23 1.540(5)
C22 H18 1.01(4)
C23 N2 1.511(4)
C23 C24 1.521(5)
C23 H19 1.00(4)
C24 C25 1.513(5)
C24 H20 0.83(5)
C25 C26 1.378(5)
C25 C30 1.391(5)
C26 C27 1.391(5)
C26 H21 0.94(7)
C27 C28 1.372(6)
C27 H22 0.95(4)
C28 C29 1.383(6)
C28 H23 1.02(5)
C29 C30 1.384(5)
C29 H24 0.99(4)
C30 H25 0.98(5)
N1 O2 1.223(4)
N1 O3 1.223(4)
N2 O5 1.217(4)
N2 O6 1.223(4)
O1 H13 0.75(5)
O4 H4A 0.84
