#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:21:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178779 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103352.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_4103352
loop_
_publ_author_name
'Malek Nechab'
'Damien Campolo'
'Julien Maury'
'Patricia Perfetti'
'Nicolas Vanthuyne'
'Didier Siri'
'Michèle P. Bertrand'
_publ_section_title
;
 Memory of Chirality in Cascade Rearrangements of Enediynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14742
_journal_page_last               14744
_journal_paper_doi               10.1021/ja106668d
_journal_volume                  132
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H33 N1 O7 S2'
_chemical_formula_sum            'C32 H33 N O7 S2'
_chemical_formula_weight         607.71
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-04-08T09:55:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 101.867(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1812(2)
_cell_length_b                   25.7846(6)
_cell_length_c                   11.8057(3)
_cell_measurement_reflns_used    29857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      1.58
_cell_measurement_wavelength     0.71073
_cell_volume                     3032.97(12)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29857
_diffrn_reflns_theta_full        28.66
_diffrn_reflns_theta_max         28.66
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1519P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2628
_reflns_number_gt                3908
_reflns_number_total             7495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106668d_si_003.cif
_cod_data_source_block           oc1s1p
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4103352
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7554(3) 0.96689(13) 0.7764(3) 0.0387(7) Uani 1 1 d . . .
C2 C 0.8035(3) 1.01688(13) 0.7836(3) 0.0428(8) Uani 1 1 d . . .
H2 H 0.8823 1.0243 0.7586 0.051 Uiso 1 1 calc R . .
C3 C 0.7353(3) 1.05717(13) 0.8283(3) 0.0449(8) Uani 1 1 d . . .
C4 C 0.7820(4) 1.10917(15) 0.8371(3) 0.0551(9) Uani 1 1 d . . .
H4 H 0.8608 1.1175 0.8129 0.066 Uiso 1 1 calc R . .
C5 C 0.7137(4) 1.14678(17) 0.8800(4) 0.0712(12) Uani 1 1 d . . .
H5 H 0.7463 1.1806 0.8865 0.085 Uiso 1 1 calc R . .
C6 C 0.5929(4) 1.13473(17) 0.9149(4) 0.0717(12) Uani 1 1 d . . .
H6 H 0.5458 1.1609 0.9434 0.086 Uiso 1 1 calc R . .
C7 C 0.5444(4) 1.08575(15) 0.9076(4) 0.0586(10) Uani 1 1 d . . .
H7 H 0.4649 1.0786 0.9318 0.07 Uiso 1 1 calc R . .
C8 C 0.6130(3) 1.04539(14) 0.8638(3) 0.0433(8) Uani 1 1 d . . .
C9 C 0.5650(3) 0.99386(13) 0.8520(3) 0.0436(8) Uani 1 1 d . . .
H9 H 0.4837 0.986 0.8722 0.052 Uiso 1 1 calc R . .
C10 C 0.6349(3) 0.95523(13) 0.8117(3) 0.0389(7) Uani 1 1 d . . .
C11 C 0.5794(4) 0.90091(14) 0.8065(3) 0.0510(9) Uani 1 1 d . . .
H11A H 0.5761 0.89 0.8845 0.061 Uiso 1 1 calc R . .
H11B H 0.4879 0.9015 0.7621 0.061 Uiso 1 1 calc R . .
C12 C 0.7294(3) 0.88227(14) 0.6680(3) 0.0420(8) Uani 1 1 d . . .
C13 C 0.8296(3) 0.92345(13) 0.7314(3) 0.0413(8) Uani 1 1 d . . .
H13 H 0.871 0.939 0.6716 0.05 Uiso 1 1 calc R . .
C14 C 0.4496(4) 0.79520(13) 0.6605(3) 0.0476(9) Uani 1 1 d . . .
C15 C 0.3289(4) 0.80959(14) 0.6895(4) 0.0555(10) Uani 1 1 d . . .
H15 H 0.3271 0.8217 0.7633 0.067 Uiso 1 1 calc R . .
C16 C 0.2125(4) 0.80548(15) 0.6069(4) 0.0644(11) Uani 1 1 d . . .
H16 H 0.1317 0.8152 0.626 0.077 Uiso 1 1 calc R . .
C17 C 0.2114(4) 0.78735(16) 0.4964(4) 0.0657(11) Uani 1 1 d . . .
C18 C 0.3326(4) 0.77302(16) 0.4711(4) 0.0650(11) Uani 1 1 d . . .
H18 H 0.3345 0.7608 0.3973 0.078 Uiso 1 1 calc R . .
C19 C 0.4508(4) 0.77625(15) 0.5517(3) 0.0555(10) Uani 1 1 d . . .
H19 H 0.5311 0.7657 0.5329 0.067 Uiso 1 1 calc R . .
C20 C 0.0840(4) 0.7841(2) 0.4058(5) 0.0986(17) Uani 1 1 d . . .
H20A H 0.0778 0.8137 0.3555 0.148 Uiso 1 1 calc R . .
H20B H 0.0083 0.7837 0.4427 0.148 Uiso 1 1 calc R . .
H20C H 0.0845 0.753 0.3614 0.148 Uiso 1 1 calc R . .
C21 C 0.6382(4) 0.91138(15) 0.5675(3) 0.0490(9) Uani 1 1 d . . .
C22 C 0.4311(4) 0.9130(2) 0.4383(4) 0.0869(15) Uani 1 1 d . . .
H22A H 0.4023 0.9477 0.4504 0.13 Uiso 1 1 calc R . .
H22B H 0.3541 0.8909 0.4168 0.13 Uiso 1 1 calc R . .
H22C H 0.4811 0.9131 0.3776 0.13 Uiso 1 1 calc R . .
C23 C 0.7987(4) 0.84162(15) 0.6056(3) 0.0535(9) Uani 1 1 d . . .
H23A H 0.8553 0.8201 0.6618 0.08 Uiso 1 1 calc R . .
H23B H 0.8522 0.8588 0.5588 0.08 Uiso 1 1 calc R . .
H23C H 0.7321 0.8206 0.5573 0.08 Uiso 1 1 calc R . .
C24 C 0.9050(3) 0.89139(14) 0.9701(3) 0.0436(8) Uani 1 1 d . . .
C25 C 0.8865(3) 0.93343(15) 1.0385(3) 0.0496(9) Uani 1 1 d . . .
H25 H 0.9042 0.9669 1.0166 0.06 Uiso 1 1 calc R . .
C26 C 0.8415(3) 0.92479(16) 1.1396(3) 0.0536(9) Uani 1 1 d . . .
H26 H 0.8294 0.9529 1.1859 0.064 Uiso 1 1 calc R . .
C27 C 0.8138(3) 0.87510(17) 1.1736(3) 0.0535(9) Uani 1 1 d . . .
C28 C 0.8322(4) 0.83401(16) 1.1037(3) 0.0581(10) Uani 1 1 d . . .
H28 H 0.8138 0.8005 1.1252 0.07 Uiso 1 1 calc R . .
C29 C 0.8777(4) 0.84156(15) 1.0015(3) 0.0522(9) Uani 1 1 d . . .
H29 H 0.8896 0.8135 0.9552 0.063 Uiso 1 1 calc R . .
C30 C 0.7661(4) 0.8668(2) 1.2851(3) 0.0793(14) Uani 1 1 d . . .
H30A H 0.8341 0.8783 1.349 0.119 Uiso 1 1 calc R . .
H30B H 0.7488 0.8306 1.2939 0.119 Uiso 1 1 calc R . .
H30C H 0.6853 0.8862 1.2831 0.119 Uiso 1 1 calc R . .
N1 N 0.6558(3) 0.86185(10) 0.7549(2) 0.0412(7) Uani 1 1 d . . .
O1 O 0.6975(3) 0.76739(10) 0.7344(2) 0.0633(7) Uani 1 1 d . . .
O2 O 0.5677(3) 0.79903(10) 0.8750(2) 0.0601(7) Uani 1 1 d . . .
O3 O 0.6784(3) 0.94495(12) 0.5135(2) 0.0722(8) Uani 1 1 d . . .
O4 O 0.5160(3) 0.89378(11) 0.5448(2) 0.0670(8) Uani 1 1 d . . .
O5 O 1.0562(2) 0.94557(11) 0.8642(2) 0.0586(7) Uani 1 1 d . . .
O6 O 1.0205(2) 0.85346(10) 0.8112(2) 0.0595(7) Uani 1 1 d . . .
S1 S 0.60096(9) 0.80216(3) 0.76321(8) 0.0478(3) Uani 1 1 d . . .
S2 S 0.96858(8) 0.90152(4) 0.84436(7) 0.0463(3) Uani 1 1 d . . .
C31 C 0.7764(11) 1.0439(4) 0.3579(10) 0.090(3) Uani 0.5 1 d P A 1
H31A H 0.7188 1.0731 0.3607 0.135 Uiso 0.5 1 calc PR A 1
H31B H 0.7265 1.0124 0.3596 0.135 Uiso 0.5 1 calc PR A 1
H31C H 0.8104 1.0452 0.2879 0.135 Uiso 0.5 1 calc PR A 1
C32 C 0.8854(8) 1.0453(5) 0.4550(8) 0.154(4) Uani 0.5 1 d P A 1
O7 O 0.9246(12) 1.0735(4) 0.5245(12) 0.156(5) Uani 0.5 1 d P A 1
O8 O 0.9519(5) 0.9996(3) 0.4499(6) 0.133(2) Uani 0.5 1 d P . 1
C33 C 0.8854(8) 1.0453(5) 0.4550(8) 0.154(4) Uani 0.5 1 d P B 2
H33A H 0.8687 1.0499 0.5315 0.231 Uiso 0.5 1 calc PR B 2
H33B H 0.8015 1.0445 0.4 0.231 Uiso 0.5 1 calc PR B 2
H33C H 0.9391 1.0735 0.437 0.231 Uiso 0.5 1 calc PR B 2
C34 C 0.9519(5) 0.9996(3) 0.4499(6) 0.133(2) Uani 0.5 1 d P . 2
H34A H 0.9923 0.9984 0.3823 0.159 Uiso 0.5 1 calc PR . 2
H34B H 0.8923 0.9702 0.4483 0.159 Uiso 0.5 1 calc PR . 2
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 0 '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 0.006 '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_3
C2 C1 C10 120.2(3) .
C2 C1 C13 121.4(3) .
C10 C1 C13 118.5(3) .
C1 C2 C3 121.2(3) .
C1 C2 H2 119.4 .
C3 C2 H2 119.4 .
C2 C3 C4 122.6(3) .
C2 C3 C8 118.7(3) .
C4 C3 C8 118.7(3) .
C5 C4 C3 120.9(4) .
C5 C4 H4 119.5 .
C3 C4 H4 119.5 .
C4 C5 C6 119.9(4) .
C4 C5 H5 120 .
C6 C5 H5 120 .
C7 C6 C5 121.1(4) .
C7 C6 H6 119.4 .
C5 C6 H6 119.4 .
C6 C7 C8 120.7(4) .
C6 C7 H7 119.7 .
C8 C7 H7 119.7 .
C7 C8 C9 122.9(3) .
C7 C8 C3 118.6(3) .
C9 C8 C3 118.5(3) .
C10 C9 C8 121.8(3) .
C10 C9 H9 119.1 .
C8 C9 H9 119.1 .
C9 C10 C1 119.7(3) .
C9 C10 C11 118.3(3) .
C1 C10 C11 121.9(3) .
N1 C11 C10 115.1(3) .
N1 C11 H11A 108.5 .
C10 C11 H11A 108.5 .
N1 C11 H11B 108.5 .
C10 C11 H11B 108.5 .
H11A C11 H11B 107.5 .
N1 C12 C23 115.9(3) .
N1 C12 C21 113.2(3) .
C23 C12 C21 103.1(3) .
N1 C12 C13 106.5(2) .
C23 C12 C13 112.1(3) .
C21 C12 C13 105.7(3) .
C1 C13 C12 110.5(2) .
C1 C13 S2 110.0(2) .
C12 C13 S2 118.3(2) .
C1 C13 H13 105.7 .
C12 C13 H13 105.7 .
S2 C13 H13 105.7 .
C19 C14 C15 120.1(4) .
C19 C14 S1 120.2(3) .
C15 C14 S1 119.7(3) .
C16 C15 C14 118.8(4) .
C16 C15 H15 120.6 .
C14 C15 H15 120.6 .
C15 C16 C17 122.2(4) .
C15 C16 H16 118.9 .
C17 C16 H16 118.9 .
C18 C17 C16 117.4(4) .
C18 C17 C20 120.7(4) .
C16 C17 C20 121.8(4) .
C19 C18 C17 122.0(4) .
C19 C18 H18 119 .
C17 C18 H18 119 .
C18 C19 C14 119.5(4) .
C18 C19 H19 120.3 .
C14 C19 H19 120.3 .
C17 C20 H20A 109.5 .
C17 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C17 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
O3 C21 O4 124.1(3) .
O3 C21 C12 123.0(3) .
O4 C21 C12 112.8(3) .
O4 C22 H22A 109.5 .
O4 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
O4 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C12 C23 H23A 109.5 .
C12 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C12 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C29 C24 C25 120.8(3) .
C29 C24 S2 119.6(3) .
C25 C24 S2 119.5(3) .
C26 C25 C24 119.0(3) .
C26 C25 H25 120.5 .
C24 C25 H25 120.5 .
C25 C26 C27 121.4(4) .
C25 C26 H26 119.3 .
C27 C26 H26 119.3 .
C28 C27 C26 118.3(3) .
C28 C27 C30 121.4(4) .
C26 C27 C30 120.3(4) .
C27 C28 C29 121.5(4) .
C27 C28 H28 119.3 .
C29 C28 H28 119.3 .
C24 C29 C28 118.9(4) .
C24 C29 H29 120.5 .
C28 C29 H29 120.5 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
C11 N1 C12 115.2(3) .
C11 N1 S1 113.5(2) .
C12 N1 S1 126.7(2) .
C21 O4 C22 115.6(3) .
O1 S1 O2 119.43(17) .
O1 S1 N1 108.37(15) .
O2 S1 N1 104.77(14) .
O1 S1 C14 108.71(16) .
O2 S1 C14 106.82(16) .
N1 S1 C14 108.27(15) .
O6 S2 O5 118.52(15) .
O6 S2 C24 108.85(16) .
O5 S2 C24 107.75(15) .
O6 S2 C13 110.06(16) .
O5 S2 C13 103.71(16) .
C24 S2 C13 107.37(15) .
C32 C31 H31A 109.5 .
C32 C31 H31B 109.5 .
H31A C31 H31B 109.5 .
C32 C31 H31C 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
O7 C32 O8 119.4(12) .
O7 C32 C31 135.8(15) .
O8 C32 C31 104.8(10) .
C32 O8 O8 102.8(9) 3_776
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.375(5) .
C1 C10 1.407(4) .
C1 C13 1.507(4) .
C2 C3 1.411(5) .
C2 H2 0.93 .
C3 C4 1.419(5) .
C3 C8 1.426(5) .
C4 C5 1.352(5) .
C4 H4 0.93 .
C5 C6 1.409(6) .
C5 H5 0.93 .
C6 C7 1.353(6) .
C6 H6 0.93 .
C7 C8 1.410(5) .
C7 H7 0.93 .
C8 C9 1.413(5) .
C9 C10 1.365(4) .
C9 H9 0.93 .
C10 C11 1.507(5) .
C11 N1 1.479(4) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C12 N1 1.486(4) .
C12 C23 1.534(4) .
C12 C21 1.544(5) .
C12 C13 1.554(5) .
C13 S2 1.823(3) .
C13 H13 0.98 .
C14 C19 1.377(5) .
C14 C15 1.391(5) .
C14 S1 1.763(4) .
C15 C16 1.376(6) .
C15 H15 0.93 .
C16 C17 1.384(6) .
C16 H16 0.93 .
C17 C18 1.379(6) .
C17 C20 1.504(6) .
C18 C19 1.375(6) .
C18 H18 0.93 .
C19 H19 0.93 .
C20 H20A 0.96 .
C20 H20B 0.96 .
C20 H20C 0.96 .
C21 O3 1.196(4) .
C21 O4 1.299(4) .
C22 O4 1.458(5) .
C22 H22A 0.96 .
C22 H22B 0.96 .
C22 H22C 0.96 .
C23 H23A 0.96 .
C23 H23B 0.96 .
C23 H23C 0.96 .
C24 C29 1.382(5) .
C24 C25 1.387(5) .
C24 S2 1.757(3) .
C25 C26 1.382(5) .
C25 H25 0.93 .
C26 C27 1.389(5) .
C26 H26 0.93 .
C27 C28 1.380(5) .
C27 C30 1.508(5) .
C28 C29 1.391(5) .
C28 H28 0.93 .
C29 H29 0.93 .
C30 H30A 0.96 .
C30 H30B 0.96 .
C30 H30C 0.96 .
N1 S1 1.647(3) .
O1 S1 1.423(3) .
O2 S1 1.431(2) .
O5 S2 1.434(3) .
O6 S2 1.433(3) .
C31 C32 1.422(13) .
C31 H31A 0.96 .
C31 H31B 0.96 .
C31 H31C 0.96 .
C32 O7 1.108(12) .
C32 O8 1.366(13) .
O8 O8 1.372(13) 3_776
