#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:38:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152344.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_7152344
loop_
_publ_author_name
'Gao, YuZhe'
'Wang, Xue'
'Sun, LiDong'
'Xie, LongGuan'
'Xu, XiaoHua'
_publ_section_title
;
 Zinc or indium-mediated Barbier-type allylation of aldehydes with
 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis
 method for α-methylene-γ-butyrolactone
;
_journal_issue                   20
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3991
_journal_paper_doi               10.1039/c2ob25397f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C21 H26 O3 S'
_chemical_formula_weight         358.48
_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                 100.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1436(18)
_cell_length_b                   19.925(4)
_cell_length_c                   10.386(2)
_cell_measurement_reflns_used    5364
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.476
_cell_measurement_theta_min      2.243
_cell_volume                     1858.4(7)
_computing_cell_refinement       crystalclear
_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13690
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0357
_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)+(0.0566P)²+0.3298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                2923
_reflns_number_total             3255
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25397f.txt
_cod_data_source_block           r90607b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1858.4(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7152344
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
S1 S 0.21295(5) 0.216827(18) 0.50349(4) 0.02580(14) Uani 1 1 d .
O1 O 0.31741(11) 0.30830(5) 0.16470(9) 0.0201(2) Uani 1 1 d .
O2 O 0.27283(13) 0.19977(5) 0.19421(10) 0.0276(3) Uani 1 1 d .
O3 O 0.67824(11) 0.35864(5) 0.45233(10) 0.0247(3) Uani 1 1 d .
H3 H 0.7256 0.3364 0.5124 0.037 Uiso 1 1 calc R
C1 C 0.34468(16) 0.42884(7) 0.19889(13) 0.0168(3) Uani 1 1 d .
C2 C 0.17925(16) 0.44501(7) 0.17087(13) 0.0184(3) Uani 1 1 d .
H2 H 0.1274 0.4130 0.1063 0.022 Uiso 1 1 calc R
C3 C 0.17758(18) 0.51562(7) 0.10646(15) 0.0242(3) Uani 1 1 d .
H3A H 0.1512 0.5120 0.0118 0.029 Uiso 1 1 calc R
H3B H 0.1059 0.5446 0.1369 0.029 Uiso 1 1 calc R
C4 C 0.33518(19) 0.54383(7) 0.14740(16) 0.0270(4) Uani 1 1 d .
H4A H 0.3665 0.5669 0.0750 0.032 Uiso 1 1 calc R
H4B H 0.3409 0.5746 0.2205 0.032 Uiso 1 1 calc R
C5 C 0.42885(17) 0.48239(7) 0.18652(14) 0.0216(3) Uani 1 1 d .
C6 C 0.59507(19) 0.48714(8) 0.21066(18) 0.0336(4) Uani 1 1 d .
H6A H 0.6373 0.4437 0.2337 0.050 Uiso 1 1 calc R
H6B H 0.6282 0.5180 0.2810 0.050 Uiso 1 1 calc R
H6C H 0.6263 0.5028 0.1327 0.050 Uiso 1 1 calc R
C7 C 0.10537(16) 0.44532(7) 0.29016(14) 0.0199(3) Uani 1 1 d .
C8 C 0.17916(18) 0.48419(8) 0.40702(14) 0.0268(4) Uani 1 1 d .
H8A H 0.1220 0.4802 0.4753 0.040 Uiso 1 1 calc R
H8B H 0.1855 0.5306 0.3836 0.040 Uiso 1 1 calc R
H8C H 0.2775 0.4668 0.4375 0.040 Uiso 1 1 calc R
C9 C -0.02447(17) 0.41430(8) 0.28607(16) 0.0274(4) Uani 1 1 d .
H9A H -0.0719 0.4165 0.3577 0.033 Uiso 1 1 calc R
H9B H -0.0676 0.3904 0.2116 0.033 Uiso 1 1 calc R
C10 C 0.40712(16) 0.36144(6) 0.24082(13) 0.0164(3) Uani 1 1 d .
H10 H 0.5083 0.3590 0.2225 0.020 Uiso 1 1 calc R
C11 C 0.41275(16) 0.33932(6) 0.38334(13) 0.0155(3) Uani 1 1 d .
H11 H 0.3164 0.3484 0.4082 0.019 Uiso 1 1 calc R
C12 C 0.43097(16) 0.26361(7) 0.36722(13) 0.0171(3) Uani 1 1 d .
H12 H 0.5338 0.2560 0.3561 0.020 Uiso 1 1 calc R
C13 C 0.33270(16) 0.25148(7) 0.23599(13) 0.0194(3) Uani 1 1 d .
C14 C 0.53531(16) 0.37347(7) 0.47982(14) 0.0201(3) Uani 1 1 d .
H14A H 0.5197 0.4216 0.4758 0.024 Uiso 1 1 calc R
H14B H 0.5308 0.3587 0.5680 0.024 Uiso 1 1 calc R
C15 C 0.40181(18) 0.21564(7) 0.47351(14) 0.0216(3) Uani 1 1 d .
H15A H 0.4692 0.2266 0.5545 0.026 Uiso 1 1 calc R
H15B H 0.4249 0.1704 0.4492 0.026 Uiso 1 1 calc R
C16 C 0.22034(17) 0.27728(7) 0.62991(14) 0.0200(3) Uani 1 1 d .
C17 C 0.32252(19) 0.27289(8) 0.74716(15) 0.0285(4) Uani 1 1 d .
H17 H 0.3945 0.2393 0.7587 0.034 Uiso 1 1 calc R
C18 C 0.3169(2) 0.31837(9) 0.84637(17) 0.0347(4) Uani 1 1 d .
H18 H 0.3863 0.3157 0.9241 0.042 Uiso 1 1 calc R
C19 C 0.2097(2) 0.36752(8) 0.83123(17) 0.0350(4) Uani 1 1 d .
H19 H 0.2053 0.3975 0.8990 0.042 Uiso 1 1 calc R
C20 C 0.1085(2) 0.37218(8) 0.71496(18) 0.0379(5) Uani 1 1 d .
H20 H 0.0362 0.4056 0.7042 0.045 Uiso 1 1 calc R
C21 C 0.11394(19) 0.32742(8) 0.61431(16) 0.0290(4) Uani 1 1 d .
H21 H 0.0459 0.3310 0.5359 0.035 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'
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
C16 S1 C15 103.38(7)
C13 O1 C10 108.62(10)
C14 O3 H3 109.5
C5 C1 C10 123.46(13)
C5 C1 C2 112.50(12)
C10 C1 C2 123.99(12)
C7 C2 C1 115.09(12)
C7 C2 C3 112.15(11)
C1 C2 C3 101.70(11)
C7 C2 H2 109.2
C1 C2 H2 109.2
C3 C2 H2 109.2
C4 C3 C2 106.26(12)
C4 C3 H3A 110.5
C2 C3 H3A 110.5
C4 C3 H3B 110.5
C2 C3 H3B 110.5
H3A C3 H3B 108.7
C5 C4 C3 103.56(12)
C5 C4 H4A 111.0
C3 C4 H4A 111.0
C5 C4 H4B 111.0
C3 C4 H4B 111.0
H4A C4 H4B 109.0
C1 C5 C6 128.30(14)
C1 C5 C4 111.51(14)
C6 C5 C4 120.15(13)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C9 C7 C8 122.10(14)
C9 C7 C2 120.18(14)
C8 C7 C2 117.64(13)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 120.0
C7 C9 H9B 120.0
H9A C9 H9B 120.0
O1 C10 C1 110.25(11)
O1 C10 C11 103.01(10)
C1 C10 C11 118.76(11)
O1 C10 H10 108.1
C1 C10 H10 108.1
C11 C10 H10 108.1
C14 C11 C12 115.62(12)
C14 C11 C10 113.25(11)
C12 C11 C10 99.32(10)
C14 C11 H11 109.4
C12 C11 H11 109.4
C10 C11 H11 109.4
C13 C12 C15 113.59(12)
C13 C12 C11 101.46(11)
C15 C12 C11 120.16(11)
C13 C12 H12 106.9
C15 C12 H12 106.9
C11 C12 H12 106.9
O2 C13 O1 121.78(13)
O2 C13 C12 127.98(13)
O1 C13 C12 110.24(11)
O3 C14 C11 111.55(11)
O3 C14 H14A 109.3
C11 C14 H14A 109.3
O3 C14 H14B 109.3
C11 C14 H14B 109.3
H14A C14 H14B 108.0
C12 C15 S1 114.80(11)
C12 C15 H15A 108.6
S1 C15 H15A 108.6
C12 C15 H15B 108.6
S1 C15 H15B 108.6
H15A C15 H15B 107.5
C21 C16 C17 119.33(14)
C21 C16 S1 118.43(12)
C17 C16 S1 122.07(11)
C18 C17 C16 119.93(15)
C18 C17 H17 120.0
C16 C17 H17 120.0
C19 C18 C17 120.57(17)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 119.66(15)
C18 C19 H19 120.2
C20 C19 H19 120.2
C19 C20 C21 120.34(16)
C19 C20 H20 119.8
C21 C20 H20 119.8
C20 C21 C16 120.16(16)
C20 C21 H21 119.9
C16 C21 H21 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C16 1.7737(14)
S1 C15 1.8116(16)
O1 C13 1.3455(17)
O1 C10 1.4748(17)
O2 C13 1.2085(17)
O3 C14 1.4203(17)
O3 H3 0.8200
C1 C5 1.336(2)
C1 C10 1.4919(18)
C1 C2 1.520(2)
C2 C7 1.519(2)
C2 C3 1.5566(19)
C2 H2 0.9800
C3 C4 1.531(2)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.505(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.496(2)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C9 1.332(2)
C7 C8 1.490(2)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9300
C9 H9B 0.9300
C10 C11 1.5360(19)
C10 H10 0.9800
C11 C14 1.517(2)
C11 C12 1.5304(18)
C11 H11 0.9800
C12 C13 1.504(2)
C12 C15 1.5213(19)
C12 H12 0.9800
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
C16 C21 1.383(2)
C16 C17 1.391(2)
C17 C18 1.380(2)
C17 H17 0.9300
C18 C19 1.374(3)
C18 H18 0.9300
C19 C20 1.379(3)
C19 H19 0.9300
C20 C21 1.382(2)
C20 H20 0.9300
C21 H21 0.9300
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
C5 C1 C2 C7 -108.51(14)
C10 C1 C2 C7 69.17(16)
C5 C1 C2 C3 12.96(15)
C10 C1 C2 C3 -169.36(12)
C7 C2 C3 C4 103.42(14)
C1 C2 C3 C4 -20.07(14)
C2 C3 C4 C5 20.24(15)
C10 C1 C5 C6 -0.2(2)
C2 C1 C5 C6 177.52(14)
C10 C1 C5 C4 -178.00(12)
C2 C1 C5 C4 -0.31(17)
C3 C4 C5 C1 -12.81(16)
C3 C4 C5 C6 169.17(13)
C1 C2 C7 C9 -133.95(14)
C3 C2 C7 C9 110.44(15)
C1 C2 C7 C8 49.20(17)
C3 C2 C7 C8 -66.41(17)
C13 O1 C10 C1 -154.42(11)
C13 O1 C10 C11 -26.72(13)
C5 C1 C10 O1 -140.44(13)
C2 C1 C10 O1 42.13(17)
C5 C1 C10 C11 101.12(17)
C2 C1 C10 C11 -76.31(17)
O1 C10 C11 C14 162.70(11)
C1 C10 C11 C14 -75.16(16)
O1 C10 C11 C12 39.51(12)
C1 C10 C11 C12 161.65(12)
C14 C11 C12 C13 -159.18(12)
C10 C11 C12 C13 -37.69(13)
C14 C11 C12 C15 74.66(17)
C10 C11 C12 C15 -163.86(13)
C10 O1 C13 O2 -178.26(13)
C10 O1 C13 C12 1.67(14)
C15 C12 C13 O2 -25.7(2)
C11 C12 C13 O2 -156.09(14)
C15 C12 C13 O1 154.38(11)
C11 C12 C13 O1 23.99(14)
C12 C11 C14 O3 52.63(16)
C10 C11 C14 O3 -61.03(15)
C13 C12 C15 S1 -58.37(14)
C11 C12 C15 S1 61.93(16)
C16 S1 C15 C12 -91.69(11)
C15 S1 C16 C21 130.15(12)
C15 S1 C16 C17 -54.55(14)
C21 C16 C17 C18 0.0(2)
S1 C16 C17 C18 -175.27(12)
C16 C17 C18 C19 1.0(3)
C17 C18 C19 C20 -1.2(2)
C18 C19 C20 C21 0.5(2)
C19 C20 C21 C16 0.5(2)
C17 C16 C21 C20 -0.7(2)
S1 C16 C21 C20 174.73(12)
