#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024929.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_4024929
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            'C21 H30 N2 O4 S'
_chemical_formula_weight         406.53
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.156(9)
_cell_angle_beta                 93.314(9)
_cell_angle_gamma                113.986(6)
_cell_formula_units_Z            2
_cell_length_a                   8.259(2)
_cell_length_b                   9.835(3)
_cell_length_c                   15.008(6)
_cell_measurement_reflns_used    1621
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1097.2(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6856
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0785
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0284P)²+3.2227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1868
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                2536
_reflns_number_total             3830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9017292_si_002_3.cif
_cod_data_source_block           16
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4024929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.18939(17) 0.58833(15) 0.39636(9) 0.0542(4) Uani 1 1 d . . .
C5 C 1.2348(6) 0.7794(5) 0.4250(3) 0.0516(12) Uani 1 1 d . . .
C4 C 1.1806(7) 0.8281(6) 0.5032(4) 0.0646(14) Uani 1 1 d . . .
H4A H 1.1274 0.7616 0.5427 0.077 Uiso 1 1 calc R . .
C2 C 1.2883(7) 1.0778(6) 0.4660(4) 0.0682(15) Uani 1 1 d . . .
C6 C 1.3162(7) 0.8777(6) 0.3676(4) 0.0690(15) Uani 1 1 d . . .
H6A H 1.3543 0.8455 0.3153 0.083 Uiso 1 1 calc R . .
C7 C 1.3402(8) 1.0256(7) 0.3892(5) 0.0775(17) Uani 1 1 d . . .
H7A H 1.3938 1.0924 0.3499 0.093 Uiso 1 1 calc R . .
C3 C 1.2064(8) 0.9759(7) 0.5220(4) 0.0730(16) Uani 1 1 d . . .
H3A H 1.1673 1.0083 0.5740 0.088 Uiso 1 1 calc R . .
C1 C 1.3139(9) 1.2399(6) 0.4878(5) 0.096(2) Uani 1 1 d . . .
H1A H 1.2690 1.2549 0.5440 0.143 Uiso 1 1 calc R . .
H1B H 1.2502 1.2624 0.4404 0.143 Uiso 1 1 calc R . .
H1C H 1.4386 1.3054 0.4927 0.143 Uiso 1 1 calc R . .
O1 O 1.1955(5) 0.5263(4) 0.4778(2) 0.0669(10) Uani 1 1 d . . .
N2 N 0.9427(5) 0.5691(4) 0.2809(3) 0.0534(10) Uani 1 1 d . . .
C8 C 0.7817(7) 0.5412(5) 0.2568(3) 0.0544(12) Uani 1 1 d . . .
C9 C 0.7531(7) 0.6210(6) 0.1827(3) 0.0608(13) Uani 1 1 d . . .
H9A H 0.6422 0.5564 0.1449 0.073 Uiso 1 1 calc R . .
H9B H 0.8495 0.6409 0.1453 0.073 Uiso 1 1 calc R . .
N1 N 0.9770(5) 0.5048(4) 0.3544(3) 0.0544(10) Uani 1 1 d . . .
H1E H 0.8975 0.4314 0.3748 0.065 Uiso 1 1 calc R . .
O2 O 1.2933(5) 0.5711(4) 0.3283(3) 0.0701(10) Uani 1 1 d . . .
C10 C 0.7456(7) 0.7700(6) 0.2208(3) 0.0600(13) Uani 1 1 d . . .
H10A H 0.8516 0.8295 0.2632 0.072 Uiso 1 1 calc R . .
H10B H 0.6431 0.7481 0.2542 0.072 Uiso 1 1 calc R . .
C11 C 0.7327(7) 0.8659(6) 0.1480(3) 0.0608(13) Uani 1 1 d . . .
C12 C 0.8894(8) 0.9107(8) 0.0943(4) 0.0803(17) Uani 1 1 d . . .
H12A H 0.8728 0.9688 0.0498 0.096 Uiso 1 1 d R . .
H12B H 0.8939 0.8206 0.0622 0.096 Uiso 1 1 d R . .
C16 C 0.7204(10) 1.0103(7) 0.1962(4) 0.0818(18) Uani 1 1 d . . .
H16A H 0.6436 0.9820 0.2443 0.098 Uiso 1 1 d R . .
C14 C 1.0591(12) 1.1213(9) 0.2196(6) 0.110(3) Uani 1 1 d . . .
H14A H 1.1659 1.1961 0.2495 0.133 Uiso 1 1 calc R . .
C15 C 0.9068(14) 1.1269(7) 0.2389(5) 0.106(3) Uani 1 1 d . . .
H15A H 0.9134 1.2071 0.2812 0.128 Uiso 1 1 calc R . .
C13 C 1.0646(9) 1.0027(9) 0.1538(5) 0.102(2) Uani 1 1 d . . .
H13A H 1.0974 0.9358 0.1855 0.122 Uiso 1 1 calc R . .
H13B H 1.1567 1.0475 0.1157 0.122 Uiso 1 1 calc R . .
C20 C 0.1975(11) 0.4821(10) 0.0900(5) 0.128(3) Uani 1 1 d . . .
H20A H 0.0811 0.4224 0.0577 0.191 Uiso 1 1 calc R . .
H20B H 0.1958 0.4695 0.1524 0.191 Uiso 1 1 calc R . .
H20C H 0.2825 0.4502 0.0643 0.191 Uiso 1 1 calc R . .
C19 C 0.2468(10) 0.6370(10) 0.0837(7) 0.132(3) Uani 1 1 d . . .
H19A H 0.1588 0.6682 0.1082 0.158 Uiso 1 1 calc R . .
H19B H 0.2475 0.6493 0.0206 0.158 Uiso 1 1 calc R . .
C18 C 0.5618(8) 0.7718(7) 0.0874(4) 0.0711(15) Uani 1 1 d . . .
O4 O 0.4214(6) 0.7326(6) 0.1324(3) 0.0966(14) Uani 1 1 d . . .
C21 C 0.6240(7) 0.4432(6) 0.2976(4) 0.0735(16) Uani 1 1 d . . .
H21A H 0.6624 0.3998 0.3437 0.110 Uiso 1 1 calc R . .
H21B H 0.5424 0.3643 0.2515 0.110 Uiso 1 1 calc R . .
H21C H 0.5655 0.5025 0.3238 0.110 Uiso 1 1 calc R . .
O3 O 0.5511(6) 0.7361(6) 0.0060(3) 0.1026(15) Uani 1 1 d . . .
C17 C 0.6358(16) 1.0823(11) 0.1307(7) 0.126(3) Uani 1 1 d . . .
H17A H 0.616(14) 1.159(12) 0.158(7) 0.189 Uiso 1 1 d . . .
H17B H 0.495(14) 0.986(11) 0.122(7) 0.189 Uiso 1 1 d . . .
H17C H 0.709(14) 1.097(11) 0.078(7) 0.189 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.4(2) . . ?
O2 S1 N1 108.7(2) . . ?
O1 S1 N1 104.0(2) . . ?
O2 S1 C5 109.3(2) . . ?
O1 S1 C5 109.2(2) . . ?
N1 S1 C5 105.2(2) . . ?
C6 C5 C4 120.6(5) . . ?
C6 C5 S1 119.8(4) . . ?
C4 C5 S1 119.6(4) . . ?
C3 C4 C5 119.1(5) . . ?
C7 C2 C3 117.5(5) . . ?
C7 C2 C1 121.6(6) . . ?
C3 C2 C1 120.8(6) . . ?
C5 C6 C7 118.5(5) . . ?
C2 C7 C6 122.5(6) . . ?
C4 C3 C2 121.8(6) . . ?
C8 N2 N1 117.2(4) . . ?
N2 C8 C21 126.0(5) . . ?
N2 C8 C9 115.2(5) . . ?
C21 C8 C9 118.8(4) . . ?
C8 C9 C10 111.5(4) . . ?
N2 N1 S1 111.3(3) . . ?
C9 C10 C11 114.4(4) . . ?
C18 C11 C12 110.8(5) . . ?
C18 C11 C16 108.8(5) . . ?
C12 C11 C16 109.3(5) . . ?
C18 C11 C10 106.4(5) . . ?
C12 C11 C10 113.0(4) . . ?
C16 C11 C10 108.5(4) . . ?
C11 C12 C13 112.1(5) . . ?
C15 C16 C11 110.0(6) . . ?
C15 C16 C17 109.7(6) . . ?
C11 C16 C17 112.5(6) . . ?
C15 C14 C13 122.3(8) . . ?
C14 C15 C16 124.7(7) . . ?
C14 C13 C12 113.7(7) . . ?
C20 C19 O4 111.7(7) . . ?
O3 C18 O4 123.0(6) . . ?
O3 C18 C11 124.8(6) . . ?
O4 C18 C11 112.2(5) . . ?
C18 O4 C19 118.8(6) . . ?
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 1.409(4) . ?
S1 O1 1.439(4) . ?
S1 N1 1.649(4) . ?
S1 C5 1.751(5) . ?
C5 C6 1.369(7) . ?
C5 C4 1.380(7) . ?
C4 C3 1.370(7) . ?
C2 C7 1.366(8) . ?
C2 C3 1.375(8) . ?
C2 C1 1.511(8) . ?
C6 C7 1.378(8) . ?
N2 C8 1.264(6) . ?
N2 N1 1.407(5) . ?
C8 C21 1.489(7) . ?
C8 C9 1.498(6) . ?
C9 C10 1.532(7) . ?
C10 C11 1.556(6) . ?
C11 C18 1.502(8) . ?
C11 C12 1.504(7) . ?
C11 C16 1.555(7) . ?
C12 C13 1.515(9) . ?
C16 C15 1.537(10) . ?
C16 C17 1.566(10) . ?
C14 C15 1.327(11) . ?
C14 C13 1.449(11) . ?
C20 C19 1.426(10) . ?
C19 O4 1.450(8) . ?
C18 O3 1.215(7) . ?
C18 O4 1.320(7) . ?
