#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024927.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_4024927
loop_
_publ_author_name
'Chuan-Cheng Liao'
'Jia-Liang Zhu'
_publ_section_title
;
Investigation on Lewis Acid Mediated Diels-Alder Reactions of
2-Phosphono-2-alkenoates. Application to Total Synthesis of
(\+-)-α-Alasken-8-one via Reductive Alkylation of Resulting Adduct
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7873
_journal_page_last               7884
_journal_paper_doi               10.1021/jo9017292
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H28 N2 O5 P S'
_chemical_formula_weight         427.46
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.689(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.9730(19)
_cell_length_b                   9.0132(7)
_cell_length_c                   23.6517(18)
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.46
_cell_volume                     4413.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11251
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0544
_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)+(0.0881P)²+7.6604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1779
_reflns_number_gt                2772
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9017292_si_002_1.cif
_cod_data_source_block           5
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18742(4) 0.18241(10) 0.08685(5) 0.0547(3) Uani 1 1 d . . .
P1 P -0.03220(4) 0.50733(10) 0.09836(5) 0.0500(3) Uani 1 1 d . . .
C1 C 0.22406(15) 0.3549(4) 0.11430(16) 0.0493(8) Uani 1 1 d . . .
C6 C 0.23987(19) 0.3971(5) 0.17513(19) 0.0631(10) Uani 1 1 d . . .
H6A H 0.2319 0.3337 0.2020 0.076 Uiso 1 1 calc R . .
C2 C 0.23658(18) 0.4469(5) 0.07449(18) 0.0628(10) Uani 1 1 d . . .
H2A H 0.2270 0.4173 0.0337 0.075 Uiso 1 1 calc R . .
C5 C 0.2678(2) 0.5345(5) 0.1961(2) 0.0723(11) Uani 1 1 d . . .
H5A H 0.2793 0.5619 0.2375 0.087 Uiso 1 1 calc R . .
C4 C 0.27876(18) 0.6314(5) 0.1569(2) 0.0666(11) Uani 1 1 d . . .
C3 C 0.26405(19) 0.5859(5) 0.0967(2) 0.0721(12) Uani 1 1 d . . .
H3A H 0.2726 0.6491 0.0701 0.086 Uiso 1 1 calc R . .
O2 O 0.20072(13) 0.1399(3) 0.03591(14) 0.0743(8) Uani 1 1 d . . .
O1 O 0.20297(13) 0.0868(3) 0.13936(15) 0.0766(8) Uani 1 1 d . . .
N1 N 0.08327(13) 0.2418(3) 0.09750(13) 0.0467(7) Uani 1 1 d . . .
N2 N 0.10880(13) 0.2100(3) 0.05413(13) 0.0493(7) Uani 1 1 d . . .
C9 C 0.02453(15) 0.2751(4) 0.07225(16) 0.0451(8) Uani 1 1 d . . .
H9A H 0.0031 0.2785 0.0287 0.054 Uiso 1 1 calc R . .
C10 C -0.01280(15) 0.3097(3) 0.10955(16) 0.0454(8) Uani 1 1 d . . .
C11 C -0.07638(17) 0.2170(4) 0.08570(19) 0.0583(10) Uani 1 1 d . . .
H11A H -0.1037 0.2617 0.1034 0.070 Uiso 1 1 calc R . .
C13 C 0.02681(19) 0.2797(4) 0.18056(17) 0.0598(10) Uani 1 1 d . . .
H13A H 0.0661 0.3383 0.1958 0.072 Uiso 1 1 calc R . .
H13B H 0.0020 0.3127 0.2025 0.072 Uiso 1 1 calc R . .
C12 C -0.0617(2) 0.0599(5) 0.1104(2) 0.0788(13) Uani 1 1 d . . .
H12A H -0.0924 -0.0126 0.0897 0.095 Uiso 1 1 calc R . .
C14 C 0.0447(2) 0.1182(5) 0.1964(2) 0.0703(11) Uani 1 1 d . . .
H14A H 0.0820 0.0948 0.1890 0.084 Uiso 1 1 calc R . .
H14B H 0.0564 0.1019 0.2406 0.084 Uiso 1 1 calc R . .
O3 O -0.06076(12) 0.5568(3) 0.03318(12) 0.0638(7) Uani 1 1 d . . .
O4 O -0.07508(14) 0.5265(3) 0.13421(14) 0.0731(8) Uani 1 1 d . . .
C16 C 0.0777(3) 0.6390(7) 0.1192(3) 0.1066(19) Uani 1 1 d . . .
H16A H 0.1066 0.5564 0.1243 0.128 Uiso 1 1 calc R . .
H16B H 0.0555 0.6612 0.0748 0.128 Uiso 1 1 calc R . .
O5 O 0.03063(13) 0.5938(3) 0.14081(12) 0.0656(7) Uani 1 1 d . . .
C18 C -0.1123(2) 0.6580(5) 0.1297(2) 0.0764(12) Uani 1 1 d . . .
H18A H -0.1570 0.6414 0.1003 0.092 Uiso 1 1 calc R . .
H18B H -0.0959 0.7398 0.1141 0.092 Uiso 1 1 calc R . .
C19 C -0.0092(2) 0.0184(5) 0.1584(2) 0.0790(13) Uani 1 1 d . . .
H19A H -0.0054 -0.0812 0.1696 0.095 Uiso 1 1 calc R . .
C20 C -0.1085(3) 0.6947(6) 0.1903(2) 0.1008(17) Uani 1 1 d . . .
H20A H -0.1338 0.7818 0.1870 0.151 Uiso 1 1 calc R . .
H20B H -0.0643 0.7134 0.2189 0.151 Uiso 1 1 calc R . .
H20C H -0.1247 0.6135 0.2055 0.151 Uiso 1 1 calc R . .
C21 C 0.1140(3) 0.7606(7) 0.1498(3) 0.134(3) Uani 1 1 d . . .
H21A H 0.1435 0.7846 0.1323 0.201 Uiso 1 1 calc R . .
H21B H 0.1379 0.7384 0.1936 0.201 Uiso 1 1 calc R . .
H21C H 0.0860 0.8435 0.1448 0.201 Uiso 1 1 calc R . .
C22 C -0.1157(2) 0.2130(5) 0.0149(2) 0.0847(14) Uani 1 1 d . . .
H22A H -0.1537 0.1539 0.0045 0.127 Uiso 1 1 calc R . .
H22B H -0.0901 0.1703 -0.0041 0.127 Uiso 1 1 calc R . .
H22C H -0.1280 0.3121 -0.0006 0.127 Uiso 1 1 calc R . .
C23 C 0.3070(2) 0.7844(5) 0.1784(3) 0.0980(16) Uani 1 1 d . . .
H23A H 0.3145 0.7990 0.2212 0.147 Uiso 1 1 calc R . .
H23B H 0.2773 0.8582 0.1524 0.147 Uiso 1 1 calc R . .
H23C H 0.3471 0.7931 0.1751 0.147 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'
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.84(18) . . ?
O2 S1 N2 103.77(16) . . ?
O1 S1 N2 108.11(16) . . ?
O2 S1 C1 107.97(16) . . ?
O1 S1 C1 108.34(18) . . ?
N2 S1 C1 107.02(15) . . ?
O3 P1 O4 116.04(16) . . ?
O3 P1 O5 113.17(15) . . ?
O4 P1 O5 102.71(16) . . ?
O3 P1 C10 114.87(16) . . ?
O4 P1 C10 101.59(14) . . ?
O5 P1 C10 107.07(15) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 S1 119.4(3) . . ?
C6 C1 S1 119.9(3) . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C23 122.0(4) . . ?
C3 C4 C23 119.8(4) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C9 N1 N2 113.7(3) . . ?
N1 N2 S1 113.9(2) . . ?
N1 C9 C10 122.7(3) . . ?
N1 C9 H9A 118.7 . . ?
C10 C9 H9A 118.7 . . ?
C9 C10 C11 111.0(3) . . ?
C9 C10 C13 112.5(3) . . ?
C11 C10 C13 108.4(3) . . ?
C9 C10 P1 106.4(2) . . ?
C11 C10 P1 109.8(2) . . ?
C13 C10 P1 108.6(2) . . ?
C12 C11 C10 110.2(3) . . ?
C12 C11 C22 109.2(4) . . ?
C10 C11 C22 115.2(3) . . ?
C12 C11 H11A 107.3 . . ?
C10 C11 H11A 107.3 . . ?
C22 C11 H11A 107.3 . . ?
C14 C13 C10 113.9(3) . . ?
C14 C13 H13A 108.8 . . ?
C10 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C10 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C19 C12 C11 124.9(4) . . ?
C19 C12 H12A 117.6 . . ?
C11 C12 H12A 117.6 . . ?
C19 C14 C13 111.6(3) . . ?
C19 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C19 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C18 O4 P1 123.0(3) . . ?
C21 C16 O5 114.6(4) . . ?
C21 C16 H16A 108.6 . . ?
O5 C16 H16A 108.6 . . ?
C21 C16 H16B 108.6 . . ?
O5 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 O5 P1 122.7(3) . . ?
O4 C18 C20 109.7(4) . . ?
O4 C18 H18A 109.7 . . ?
C20 C18 H18A 109.7 . . ?
O4 C18 H18B 109.7 . . ?
C20 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C12 C19 C14 124.8(4) . . ?
C12 C19 H19A 117.6 . . ?
C14 C19 H19A 117.6 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.418(3) . ?
S1 O1 1.424(3) . ?
S1 N2 1.646(3) . ?
S1 C1 1.753(4) . ?
P1 O3 1.459(3) . ?
P1 O4 1.563(3) . ?
P1 O5 1.563(3) . ?
P1 C10 1.827(3) . ?
C1 C2 1.376(5) . ?
C1 C6 1.376(5) . ?
C6 C5 1.384(6) . ?
C6 H6A 0.9300 . ?
C2 C3 1.399(6) . ?
C2 H2A 0.9300 . ?
C5 C4 1.374(6) . ?
C5 H5A 0.9300 . ?
C4 C3 1.375(6) . ?
C4 C23 1.515(6) . ?
C3 H3A 0.9300 . ?
N1 C9 1.253(4) . ?
N1 N2 1.414(3) . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.561(5) . ?
C10 C13 1.548(5) . ?
C11 C12 1.513(5) . ?
C11 C22 1.521(6) . ?
C11 H11A 0.9800 . ?
C13 C14 1.515(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C19 1.302(6) . ?
C12 H12A 0.9300 . ?
C14 C19 1.479(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O4 C18 1.438(4) . ?
C16 C21 1.378(7) . ?
C16 O5 1.440(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C20 1.437(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
