#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/55/4025559.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_4025559
loop_
_publ_author_name
'Hua Yang'
'Rich G. Carter'
_publ_section_title
;
 Development of an Enantioselective Route toward the Lycopodium Alkaloids:
 Total Synthesis of Lycopodine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4929
_journal_page_last               4938
_journal_paper_doi               10.1021/jo100916x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C19 H25 N3 O4 S'
_chemical_formula_weight         391.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2466(8)
_cell_length_b                   11.9082(9)
_cell_length_c                   14.2975(10)
_cell_measurement_reflns_used    4979
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.50
_cell_measurement_theta_min      2.23
_cell_volume                     1914.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector Bruker Apex'
_diffrn_measurement_method       'phi and omega 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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21488
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9726
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0356
_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)+(0.0440P)²+0.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                3791
_reflns_number_total             4185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100916x_si_004.cif
_cod_data_source_block           compound3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025559
loop_
_symmetry_equiv_pos_as_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_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 0.16400(5) 0.42005(4) 0.04683(3) 0.02751(12) Uani 1 1 d . . .
O1 O -0.02332(12) 0.40142(11) 0.23760(11) 0.0378(4) Uani 1 1 d . . .
O2 O 0.30523(12) 0.81579(12) 0.16818(10) 0.0372(4) Uani 1 1 d . . .
O3 O 0.28019(13) 0.45060(12) 0.01376(10) 0.0392(4) Uani 1 1 d . . .
O4 O 0.06373(14) 0.44272(12) -0.01265(10) 0.0380(4) Uani 1 1 d . . .
N1 N 0.40872(19) 0.25652(16) 0.27820(14) 0.0494(5) Uani 1 1 d . . .
N2 N 0.43271(17) 0.18783(16) 0.33936(15) 0.0453(5) Uani 1 1 d . . .
N3 N 0.4534(3) 0.1165(2) 0.38914(18) 0.0712(7) Uani 1 1 d . . .
C1 C 0.14117(15) 0.48994(15) 0.16206(12) 0.0243(4) Uani 1 1 d . . .
C2 C 0.17546(18) 0.61625(15) 0.15039(13) 0.0245(4) Uani 1 1 d . . .
C3 C 0.08556(19) 0.67975(16) 0.08951(14) 0.0286(4) Uani 1 1 d . . .
C4 C -0.04128(18) 0.67529(17) 0.12766(15) 0.0308(4) Uani 1 1 d . . .
C5 C -0.08114(19) 0.55421(18) 0.14084(16) 0.0342(5) Uani 1 1 d . . .
C6 C 0.00766(17) 0.47589(15) 0.18533(14) 0.0280(4) Uani 1 1 d . . .
C7 C 0.21665(16) 0.42745(16) 0.23574(13) 0.0262(4) Uani 1 1 d . . .
C8 C 0.35116(18) 0.44537(18) 0.23281(15) 0.0316(4) Uani 1 1 d . . .
C9 C 0.4133(2) 0.37679(18) 0.30711(16) 0.0370(5) Uani 1 1 d . . .
C10 C 0.19058(17) 0.67476(16) 0.24554(14) 0.0271(4) Uani 1 1 d . . .
C11 C 0.27000(17) 0.77713(16) 0.24122(14) 0.0279(4) Uani 1 1 d . . .
C12 C 0.3064(2) 0.8262(2) 0.33350(17) 0.0425(6) Uani 1 1 d . . .
C13 C -0.1270(2) 0.7388(2) 0.06432(19) 0.0420(5) Uani 1 1 d . . .
C14 C 0.16295(18) 0.27337(15) 0.06810(12) 0.0268(4) Uani 1 1 d . . .
C15 C 0.2693(2) 0.21679(18) 0.08220(15) 0.0317(5) Uani 1 1 d . . .
C16 C 0.2673(2) 0.10083(18) 0.09255(16) 0.0390(5) Uani 1 1 d . . .
C17 C 0.1609(2) 0.04391(18) 0.08824(16) 0.0411(5) Uani 1 1 d . . .
C18 C 0.0553(2) 0.10017(18) 0.07347(16) 0.0385(5) Uani 1 1 d . . .
C19 C 0.0558(2) 0.21625(17) 0.06390(14) 0.0307(4) Uani 1 1 d . . .
H2 H 0.2472(17) 0.6142(15) 0.1227(13) 0.016(5) Uiso 1 1 d . . .
H3A H 0.0848(16) 0.6487(15) 0.0239(13) 0.019(5) Uiso 1 1 d . . .
H3B H 0.1106(16) 0.7596(16) 0.0864(13) 0.019(5) Uiso 1 1 d . . .
H4 H -0.0437(18) 0.7077(17) 0.1891(15) 0.026(5) Uiso 1 1 d . . .
H5A H -0.099(2) 0.5204(19) 0.0773(16) 0.044(6) Uiso 1 1 d . . .
H5B H -0.156(2) 0.5475(19) 0.1738(16) 0.045(6) Uiso 1 1 d . . .
H7A H 0.1988(14) 0.3492(15) 0.2321(12) 0.008(4) Uiso 1 1 d . . .
H7B H 0.1875(15) 0.4519(16) 0.2973(14) 0.020(5) Uiso 1 1 d . . .
H8A H 0.3705(16) 0.5223(18) 0.2401(14) 0.028(5) Uiso 1 1 d . . .
H8B H 0.3808(18) 0.4286(17) 0.1717(15) 0.030(5) Uiso 1 1 d . . .
H9A H 0.3679(19) 0.3868(17) 0.3675(15) 0.029(5) Uiso 1 1 d . . .
H9B H 0.502(2) 0.4015(18) 0.3099(17) 0.047(7) Uiso 1 1 d . . .
H10A H 0.1095(19) 0.7023(19) 0.2688(15) 0.035(6) Uiso 1 1 d . . .
H10B H 0.2235(18) 0.6244(18) 0.2913(16) 0.034(6) Uiso 1 1 d . . .
H12A H 0.345(2) 0.900(2) 0.329(2) 0.065(8) Uiso 1 1 d . . .
H12B H 0.241(2) 0.825(2) 0.380(2) 0.058(8) Uiso 1 1 d . . .
H12C H 0.363(3) 0.780(2) 0.357(2) 0.067(9) Uiso 1 1 d . . .
H13A H -0.125(2) 0.708(2) 0.0005(19) 0.050(7) Uiso 1 1 d . . .
H13B H -0.209(2) 0.730(2) 0.0886(17) 0.041(7) Uiso 1 1 d . . .
H13C H -0.100(2) 0.823(2) 0.0574(16) 0.049(7) Uiso 1 1 d . . .
H15 H 0.337(2) 0.2565(19) 0.0811(16) 0.039(6) Uiso 1 1 d . . .
H16 H 0.335(2) 0.0607(18) 0.1031(15) 0.035(6) Uiso 1 1 d . . .
H17 H 0.159(2) -0.036(2) 0.0903(16) 0.047(6) Uiso 1 1 d . . .
H18 H -0.016(2) 0.063(2) 0.0656(18) 0.056(8) Uiso 1 1 d . . .
H19 H -0.012(2) 0.254(2) 0.0551(16) 0.041(7) 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
O3 S1 O4 118.11(9) . . ?
O3 S1 C14 108.18(9) . . ?
O4 S1 C14 106.33(9) . . ?
O3 S1 C1 107.66(8) . . ?
O4 S1 C1 109.32(8) . . ?
C14 S1 C1 106.71(8) . . ?
N2 N1 C9 115.77(19) . . ?
N3 N2 N1 173.2(3) . . ?
C7 C1 C6 109.56(15) . . ?
C7 C1 C2 113.65(15) . . ?
C6 C1 C2 111.52(15) . . ?
C7 C1 S1 108.19(12) . . ?
C6 C1 S1 106.00(12) . . ?
C2 C1 S1 107.56(12) . . ?
C3 C2 C10 110.59(16) . . ?
C3 C2 C1 111.88(16) . . ?
C10 C2 C1 111.67(15) . . ?
C3 C2 H2 110.8(12) . . ?
C10 C2 H2 107.6(12) . . ?
C1 C2 H2 104.0(11) . . ?
C4 C3 C2 113.31(16) . . ?
C4 C3 H3A 108.2(11) . . ?
C2 C3 H3A 110.7(11) . . ?
C4 C3 H3B 108.3(11) . . ?
C2 C3 H3B 108.1(11) . . ?
H3A C3 H3B 108.1(15) . . ?
C5 C4 C13 110.97(18) . . ?
C5 C4 C3 110.62(16) . . ?
C13 C4 C3 111.16(18) . . ?
C5 C4 H4 105.0(12) . . ?
C13 C4 H4 109.1(12) . . ?
C3 C4 H4 109.8(12) . . ?
C6 C5 C4 116.32(17) . . ?
C6 C5 H5A 105.2(13) . . ?
C4 C5 H5A 108.9(13) . . ?
C6 C5 H5B 108.7(14) . . ?
C4 C5 H5B 113.3(13) . . ?
H5A C5 H5B 103.4(18) . . ?
O1 C6 C5 121.53(18) . . ?
O1 C6 C1 119.42(17) . . ?
C5 C6 C1 119.04(17) . . ?
C8 C7 C1 117.27(16) . . ?
C8 C7 H7A 110.1(9) . . ?
C1 C7 H7A 108.5(10) . . ?
C8 C7 H7B 108.2(11) . . ?
C1 C7 H7B 106.6(11) . . ?
H7A C7 H7B 105.5(15) . . ?
C9 C8 C7 111.30(18) . . ?
C9 C8 H8A 109.8(12) . . ?
C7 C8 H8A 111.1(12) . . ?
C9 C8 H8B 111.6(12) . . ?
C7 C8 H8B 109.9(12) . . ?
H8A C8 H8B 102.8(17) . . ?
N1 C9 C8 107.94(17) . . ?
N1 C9 H9A 109.4(12) . . ?
C8 C9 H9A 107.6(12) . . ?
N1 C9 H9B 108.4(13) . . ?
C8 C9 H9B 108.5(13) . . ?
H9A C9 H9B 114.7(18) . . ?
C11 C10 C2 113.23(16) . . ?
C11 C10 H10A 106.3(12) . . ?
C2 C10 H10A 109.5(12) . . ?
C11 C10 H10B 107.6(12) . . ?
C2 C10 H10B 111.2(13) . . ?
H10A C10 H10B 108.8(17) . . ?
O2 C11 C12 121.49(19) . . ?
O2 C11 C10 122.41(18) . . ?
C12 C11 C10 116.07(18) . . ?
C11 C12 H12A 114.1(17) . . ?
C11 C12 H12B 112.2(16) . . ?
H12A C12 H12B 113(2) . . ?
C11 C12 H12C 106.4(19) . . ?
H12A C12 H12C 105(2) . . ?
H12B C12 H12C 105(2) . . ?
C4 C13 H13A 110.3(14) . . ?
C4 C13 H13B 109.2(14) . . ?
H13A C13 H13B 108(2) . . ?
C4 C13 H13C 110.4(13) . . ?
H13A C13 H13C 105(2) . . ?
H13B C13 H13C 113.4(19) . . ?
C19 C14 C15 121.19(17) . . ?
C19 C14 S1 118.82(15) . . ?
C15 C14 S1 119.84(16) . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15 118.2(15) . . ?
C16 C15 H15 122.8(15) . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 118.4(14) . . ?
C15 C16 H16 121.7(14) . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 121.0(15) . . ?
C18 C17 H17 117.8(15) . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 122.4(16) . . ?
C19 C18 H18 117.8(16) . . ?
C14 C19 C18 119.2(2) . . ?
C14 C19 H19 120.5(15) . . ?
C18 C19 H19 120.3(15) . . ?
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 O3 1.4365(15) . ?
S1 O4 1.4380(15) . ?
S1 C14 1.7730(18) . ?
S1 C1 1.8634(18) . ?
O1 C6 1.211(2) . ?
O2 C11 1.208(2) . ?
N1 N2 1.227(3) . ?
N1 C9 1.492(3) . ?
N2 N3 1.132(3) . ?
C1 C7 1.544(3) . ?
C1 C6 1.547(3) . ?
C1 C2 1.562(2) . ?
C2 C3 1.534(3) . ?
C2 C10 1.538(3) . ?
C2 H2 0.90(2) . ?
C3 C4 1.528(3) . ?
C3 H3A 1.008(19) . ?
C3 H3B 0.993(19) . ?
C4 C5 1.522(3) . ?
C4 C13 1.523(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.507(3) . ?
C5 H5A 1.01(2) . ?
C5 H5B 0.97(2) . ?
C7 C8 1.528(3) . ?
C7 H7A 0.955(17) . ?
C7 H7B 0.983(19) . ?
C8 C9 1.511(3) . ?
C8 H8A 0.95(2) . ?
C8 H8B 0.96(2) . ?
C9 H9A 1.01(2) . ?
C9 H9B 1.04(2) . ?
C10 C11 1.513(3) . ?
C10 H10A 1.02(2) . ?
C10 H10B 0.96(2) . ?
C11 C12 1.500(3) . ?
C12 H12A 0.98(3) . ?
C12 H12B 0.99(3) . ?
C12 H12C 0.91(3) . ?
C13 H13A 0.98(3) . ?
C13 H13B 0.99(2) . ?
C13 H13C 1.05(2) . ?
C14 C19 1.385(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.89(2) . ?
C16 C17 1.377(3) . ?
C16 H16 0.91(2) . ?
C17 C18 1.380(3) . ?
C17 H17 0.95(2) . ?
C18 C19 1.389(3) . ?
C18 H18 0.92(3) . ?
C19 H19 0.90(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 N3 -178(2) . . . . ?
O3 S1 C1 C7 -74.09(14) . . . . ?
O4 S1 C1 C7 156.45(12) . . . . ?
C14 S1 C1 C7 41.85(14) . . . . ?
O3 S1 C1 C6 168.47(12) . . . . ?
O4 S1 C1 C6 39.01(14) . . . . ?
C14 S1 C1 C6 -75.59(14) . . . . ?
O3 S1 C1 C2 49.07(14) . . . . ?
O4 S1 C1 C2 -80.40(14) . . . . ?
C14 S1 C1 C2 165.00(13) . . . . ?
C7 C1 C2 C3 -170.30(15) . . . . ?
C6 C1 C2 C3 -45.9(2) . . . . ?
S1 C1 C2 C3 69.96(17) . . . . ?
C7 C1 C2 C10 -45.7(2) . . . . ?
C6 C1 C2 C10 78.7(2) . . . . ?
S1 C1 C2 C10 -165.48(13) . . . . ?
C10 C2 C3 C4 -67.0(2) . . . . ?
C1 C2 C3 C4 58.2(2) . . . . ?
C2 C3 C4 C5 -55.8(2) . . . . ?
C2 C3 C4 C13 -179.60(18) . . . . ?
C13 C4 C5 C6 168.0(2) . . . . ?
C3 C4 C5 C6 44.1(2) . . . . ?
C4 C5 C6 O1 144.7(2) . . . . ?
C4 C5 C6 C1 -36.5(3) . . . . ?
C7 C1 C6 O1 -18.1(2) . . . . ?
C2 C1 C6 O1 -144.80(18) . . . . ?
S1 C1 C6 O1 98.43(19) . . . . ?
C7 C1 C6 C5 163.01(17) . . . . ?
C2 C1 C6 C5 36.3(2) . . . . ?
S1 C1 C6 C5 -80.47(18) . . . . ?
C6 C1 C7 C8 -171.48(16) . . . . ?
C2 C1 C7 C8 -46.0(2) . . . . ?
S1 C1 C7 C8 73.39(18) . . . . ?
C1 C7 C8 C9 -178.49(17) . . . . ?
N2 N1 C9 C8 -165.3(2) . . . . ?
C7 C8 C9 N1 72.1(2) . . . . ?
C3 C2 C10 C11 -78.6(2) . . . . ?
C1 C2 C10 C11 156.11(16) . . . . ?
C2 C10 C11 O2 8.5(3) . . . . ?
C2 C10 C11 C12 -169.43(19) . . . . ?
O3 S1 C14 C19 -154.47(15) . . . . ?
O4 S1 C14 C19 -26.67(17) . . . . ?
C1 S1 C14 C19 89.94(16) . . . . ?
O3 S1 C14 C15 21.16(18) . . . . ?
O4 S1 C14 C15 148.96(15) . . . . ?
C1 S1 C14 C15 -94.43(16) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
S1 C14 C15 C16 -175.76(16) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C15 C14 C19 C18 -0.4(3) . . . . ?
S1 C14 C19 C18 175.19(16) . . . . ?
C17 C18 C19 C14 0.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26628009
