#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503171.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_1503171
loop_
_publ_author_name
'Xie, Peizhong'
'Huang, You'
'Chen, Ruyu'
_publ_section_title
;
 Phosphine-catalyzed domino reaction: highly stereoselective synthesis of
 trans-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and
 allylic carbonates.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3768
_journal_page_last               3771
_journal_paper_doi               10.1021/ol101611v
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C25 H23 Br N O3 P S'
_chemical_formula_sum            'C25 H23 Br N O3 P S'
_chemical_formula_weight         528.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 110.871(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2760(10)
_cell_length_b                   22.735(3)
_cell_length_c                   11.8940(15)
_cell_measurement_reflns_used    8978
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.80
_cell_volume                     2343.7(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22426
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_T_max  0.8297
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                4613
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101611v_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1503171
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.35433(2) 0.613823(9) 0.986911(17) 0.02764(7) Uani 1 1 d .
S1 S 0.64306(5) 0.538892(19) 0.37270(4) 0.02058(10) Uani 1 1 d .
P1 P 0.55205(4) 0.594608(18) 0.45396(4) 0.01415(10) Uani 1 1 d .
O1 O 0.89504(12) 0.54047(5) 0.85850(11) 0.0188(3) Uani 1 1 d .
O2 O 0.98137(13) 0.66659(5) 0.81843(12) 0.0256(3) Uani 1 1 d .
O3 O 1.12076(13) 0.66595(5) 0.69787(12) 0.0237(3) Uani 1 1 d .
N1 N 0.56693(15) 0.58047(6) 0.59396(13) 0.0159(3) Uani 1 1 d .
C1 C 0.69825(17) 0.59464(7) 0.70248(15) 0.0148(3) Uani 1 1 d .
H1 H 0.7282 0.6367 0.6993 0.018 Uiso 1 1 calc R
C2 C 0.84379(17) 0.55472(7) 0.72999(15) 0.0159(3) Uani 1 1 d .
H2 H 0.8120 0.5174 0.6832 0.019 Uiso 1 1 calc R
C3 C 0.77637(17) 0.55427(7) 0.89674(15) 0.0161(3) Uani 1 1 d .
C4 C 0.65863(17) 0.58490(7) 0.81253(15) 0.0150(3) Uani 1 1 d .
C5 C 0.53034(18) 0.60211(7) 0.83722(16) 0.0170(3) Uani 1 1 d .
H5 H 0.4480 0.6229 0.7796 0.020 Uiso 1 1 calc R
C6 C 0.52651(18) 0.58796(7) 0.94917(16) 0.0195(4) Uani 1 1 d .
C7 C 0.64393(18) 0.55687(8) 1.03436(16) 0.0210(4) Uani 1 1 d .
H7 H 0.6370 0.5478 1.1102 0.025 Uiso 1 1 calc R
C8 C 0.77218(19) 0.53905(7) 1.00787(16) 0.0195(4) Uani 1 1 d .
H8 H 0.8535 0.5173 1.0642 0.023 Uiso 1 1 calc R
C9 C 0.97677(17) 0.58060(7) 0.70294(16) 0.0172(3) Uani 1 1 d .
C10 C 1.0476(2) 0.54996(8) 0.64304(18) 0.0254(4) Uani 1 1 d .
H10A H 1.1321 0.5667 0.6270 0.031 Uiso 1 1 calc R
H10B H 1.0138 0.5113 0.6162 0.031 Uiso 1 1 calc R
C11 C 1.02498(17) 0.64143(7) 0.74715(16) 0.0195(4) Uani 1 1 d .
C12 C 1.1667(2) 0.72644(8) 0.7362(2) 0.0303(5) Uani 1 1 d .
H12A H 1.2197 0.7281 0.8246 0.036 Uiso 1 1 calc R
H12B H 1.0747 0.7522 0.7139 0.036 Uiso 1 1 calc R
C13 C 1.2728(3) 0.74629(9) 0.6746(3) 0.0473(6) Uani 1 1 d .
H13A H 1.3654 0.7216 0.7001 0.057 Uiso 1 1 calc R
H13B H 1.3022 0.7873 0.6958 0.057 Uiso 1 1 calc R
H13C H 1.2205 0.7430 0.5873 0.057 Uiso 1 1 calc R
C14 C 0.63232(17) 0.66784(7) 0.46228(16) 0.0167(3) Uani 1 1 d .
C15 C 0.73010(19) 0.68041(8) 0.40036(17) 0.0236(4) Uani 1 1 d .
H15 H 0.7536 0.6508 0.3532 0.028 Uiso 1 1 calc R
C16 C 0.7940(2) 0.73638(8) 0.4072(2) 0.0310(5) Uani 1 1 d .
H16 H 0.8605 0.7450 0.3644 0.037 Uiso 1 1 calc R
C17 C 0.7607(2) 0.77914(8) 0.47595(19) 0.0306(5) Uani 1 1 d .
H17 H 0.8062 0.8170 0.4818 0.037 Uiso 1 1 calc R
C18 C 0.6617(2) 0.76754(8) 0.53664(18) 0.0291(4) Uani 1 1 d .
H18 H 0.6383 0.7974 0.5834 0.035 Uiso 1 1 calc R
C19 C 0.5963(2) 0.71209(8) 0.52915(17) 0.0232(4) Uani 1 1 d .
H19 H 0.5268 0.7042 0.5697 0.028 Uiso 1 1 calc R
C20 C 0.34508(18) 0.60166(7) 0.37869(15) 0.0158(3) Uani 1 1 d .
C21 C 0.27945(19) 0.59060(7) 0.25575(16) 0.0196(4) Uani 1 1 d .
H21 H 0.3420 0.5766 0.2132 0.024 Uiso 1 1 calc R
C22 C 0.1229(2) 0.60001(8) 0.19501(17) 0.0240(4) Uani 1 1 d .
H22 H 0.0790 0.5936 0.1107 0.029 Uiso 1 1 calc R
C23 C 0.0311(2) 0.61864(8) 0.25730(18) 0.0263(4) Uani 1 1 d .
H23 H -0.0763 0.6244 0.2160 0.032 Uiso 1 1 calc R
C24 C 0.0955(2) 0.62905(8) 0.38020(19) 0.0279(4) Uani 1 1 d .
H24 H 0.0319 0.6418 0.4229 0.033 Uiso 1 1 calc R
C25 C 0.25211(19) 0.62093(7) 0.44072(17) 0.0214(4) Uani 1 1 d .
H25 H 0.2960 0.6285 0.5246 0.026 Uiso 1 1 calc R
H1A H 0.518(2) 0.5505(9) 0.5993(18) 0.028(6) Uiso 1 1 d .
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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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
N1 P1 C14 103.80(8)
N1 P1 C20 102.02(7)
C14 P1 C20 106.73(7)
N1 P1 S1 118.40(5)
C14 P1 S1 112.36(6)
C20 P1 S1 112.36(6)
C3 O1 C2 107.18(12)
C11 O3 C12 114.64(13)
C1 N1 P1 126.26(11)
C1 N1 H1A 114.7(14)
P1 N1 H1A 112.5(14)
N1 C1 C4 110.66(13)
N1 C1 C2 116.33(13)
C4 C1 C2 101.19(13)
N1 C1 H1 109.4
C4 C1 H1 109.4
C2 C1 H1 109.4
O1 C2 C9 108.90(13)
O1 C2 C1 106.37(12)
C9 C2 C1 116.25(13)
O1 C2 H2 108.4
C9 C2 H2 108.4
C1 C2 H2 108.4
O1 C3 C4 113.39(15)
O1 C3 C8 124.13(15)
C4 C3 C8 122.48(15)
C3 C4 C5 120.56(16)
C3 C4 C1 109.41(14)
C5 C4 C1 130.03(15)
C4 C5 C6 117.32(15)
C4 C5 H5 121.3
C6 C5 H5 121.3
C5 C6 C7 122.61(16)
C5 C6 Br1 117.89(13)
C7 C6 Br1 119.49(13)
C6 C7 C8 119.58(16)
C6 C7 H7 120.2
C8 C7 H7 120.2
C3 C8 C7 117.43(15)
C3 C8 H8 121.3
C7 C8 H8 121.3
C10 C9 C11 122.22(15)
C10 C9 C2 120.77(15)
C11 C9 C2 117.01(14)
C9 C10 H10A 120.0
C9 C10 H10B 120.0
H10A C10 H10B 120.0
O2 C11 O3 123.23(15)
O2 C11 C9 123.68(15)
O3 C11 C9 113.08(14)
O3 C12 C13 107.50(15)
O3 C12 H12A 110.2
C13 C12 H12A 110.2
O3 C12 H12B 110.2
C13 C12 H12B 110.2
H12A C12 H12B 108.5
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 C19 119.27(16)
C15 C14 P1 119.62(13)
C19 C14 P1 121.11(13)
C14 C15 C16 120.13(18)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 120.00(18)
C17 C16 H16 120.0
C15 C16 H16 120.0
C16 C17 C18 120.53(17)
C16 C17 H17 119.7
C18 C17 H17 119.7
C17 C18 C19 119.77(19)
C17 C18 H18 120.1
C19 C18 H18 120.1
C18 C19 C14 120.26(17)
C18 C19 H19 119.9
C14 C19 H19 119.9
C25 C20 C21 119.50(15)
C25 C20 P1 120.91(13)
C21 C20 P1 119.51(13)
C22 C21 C20 120.23(17)
C22 C21 H21 119.9
C20 C21 H21 119.9
C23 C22 C21 119.93(18)
C23 C22 H22 120.0
C21 C22 H22 120.0
C22 C23 C24 120.11(17)
C22 C23 H23 119.9
C24 C23 H23 119.9
C25 C24 C23 120.18(18)
C25 C24 H24 119.9
C23 C24 H24 119.9
C24 C25 C20 120.02(17)
C24 C25 H25 120.0
C20 C25 H25 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.8997(16)
S1 P1 1.9577(6)
P1 N1 1.6527(15)
P1 C14 1.8120(16)
P1 C20 1.8134(16)
O1 C3 1.3688(19)
O1 C2 1.466(2)
O2 C11 1.206(2)
O3 C11 1.347(2)
O3 C12 1.464(2)
N1 C1 1.461(2)
N1 H1A 0.83(2)
C1 C4 1.497(2)
C1 C2 1.562(2)
C1 H1 1.0000
C2 C9 1.501(2)
C2 H2 1.0000
C3 C4 1.379(2)
C3 C8 1.380(2)
C4 C5 1.380(2)
C5 C6 1.383(2)
C5 H5 0.9500
C6 C7 1.388(2)
C7 C8 1.395(2)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.326(2)
C9 C11 1.491(2)
C10 H10A 0.9500
C10 H10B 0.9500
C12 C13 1.492(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.387(2)
C14 C19 1.395(2)
C15 C16 1.394(2)
C15 H15 0.9500
C16 C17 1.374(3)
C16 H16 0.9500
C17 C18 1.381(3)
C17 H17 0.9500
C18 C19 1.388(2)
C18 H18 0.9500
C19 H19 0.9500
C20 C25 1.390(2)
C20 C21 1.392(2)
C21 C22 1.389(2)
C21 H21 0.9500
C22 C23 1.379(3)
C22 H22 0.9500
C23 C24 1.388(3)
C23 H23 0.9500
C24 C25 1.385(2)
C24 H24 0.9500
C25 H25 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
C14 P1 N1 C1 -41.22(15)
C20 P1 N1 C1 -152.03(13)
S1 P1 N1 C1 84.10(14)
P1 N1 C1 C4 169.92(11)
P1 N1 C1 C2 -75.37(18)
C3 O1 C2 C9 141.27(13)
C3 O1 C2 C1 15.27(15)
N1 C1 C2 O1 -134.82(14)
C4 C1 C2 O1 -14.87(15)
N1 C1 C2 C9 103.75(17)
C4 C1 C2 C9 -136.30(15)
C2 O1 C3 C4 -9.53(17)
C2 O1 C3 C8 170.00(15)
O1 C3 C4 C5 180.00(14)
C8 C3 C4 C5 0.5(2)
O1 C3 C4 C1 -0.68(19)
C8 C3 C4 C1 179.78(15)
N1 C1 C4 C3 133.61(14)
C2 C1 C4 C3 9.70(17)
N1 C1 C4 C5 -47.2(2)
C2 C1 C4 C5 -171.07(17)
C3 C4 C5 C6 0.7(2)
C1 C4 C5 C6 -178.46(16)
C4 C5 C6 C7 -1.1(3)
C4 C5 C6 Br1 177.74(12)
C5 C6 C7 C8 0.3(3)
Br1 C6 C7 C8 -178.49(13)
O1 C3 C8 C7 179.28(15)
C4 C3 C8 C7 -1.2(2)
C6 C7 C8 C3 0.8(2)
O1 C2 C9 C10 107.15(18)
C1 C2 C9 C10 -132.77(18)
O1 C2 C9 C11 -72.39(17)
C1 C2 C9 C11 47.7(2)
C12 O3 C11 O2 -0.9(2)
C12 O3 C11 C9 178.13(14)
C10 C9 C11 O2 -167.00(18)
C2 C9 C11 O2 12.5(2)
C10 C9 C11 O3 14.0(2)
C2 C9 C11 O3 -166.50(14)
C11 O3 C12 C13 179.44(17)
N1 P1 C14 C15 137.43(14)
C20 P1 C14 C15 -115.25(15)
S1 P1 C14 C15 8.34(16)
N1 P1 C14 C19 -43.17(15)
C20 P1 C14 C19 64.15(16)
S1 P1 C14 C19 -172.27(12)
C19 C14 C15 C16 1.3(3)
P1 C14 C15 C16 -179.25(14)
C14 C15 C16 C17 0.3(3)
C15 C16 C17 C18 -1.4(3)
C16 C17 C18 C19 0.6(3)
C17 C18 C19 C14 1.1(3)
C15 C14 C19 C18 -2.1(3)
P1 C14 C19 C18 178.55(14)
N1 P1 C20 C25 28.79(15)
C14 P1 C20 C25 -79.79(15)
S1 P1 C20 C25 156.64(12)
N1 P1 C20 C21 -154.59(13)
C14 P1 C20 C21 96.83(14)
S1 P1 C20 C21 -26.75(15)
C25 C20 C21 C22 1.5(2)
P1 C20 C21 C22 -175.20(13)
C20 C21 C22 C23 -2.0(3)
C21 C22 C23 C24 1.2(3)
C22 C23 C24 C25 0.2(3)
C23 C24 C25 C20 -0.7(3)
C21 C20 C25 C24 -0.1(3)
P1 C20 C25 C24 176.52(14)
