#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:14:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178774 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/28/4102854.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_4102854
loop_
_publ_author_name
'Xiaohua Li'
'Samuel J. Danishefsky'
_publ_section_title
;
 Cyclobutenone as a Highly Reactive Dienophile: Expanding Upon Diels-Alder
 Paradigms
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11004
_journal_page_last               11005
_journal_paper_doi               10.1021/ja1056888
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C24 H30 Cl2 N4 O6 S2'
_chemical_formula_weight         605.54
_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                102.312(15)
_cell_angle_beta                 97.659(15)
_cell_angle_gamma                90.560(16)
_cell_formula_units_Z            2
_cell_length_a                   8.487(9)
_cell_length_b                   11.047(12)
_cell_length_c                   15.467(17)
_cell_measurement_reflns_used    645
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      17.89
_cell_measurement_theta_min      2.61
_cell_volume                     1403(3)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.6133
_diffrn_reflns_av_sigmaI/netI    1.4898
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17165
_diffrn_reflns_theta_full        31.21
_diffrn_reflns_theta_max         31.21
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ROD
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         8726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.5785
_refine_ls_R_factor_gt           0.1455
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2807
_refine_ls_wR_factor_ref         0.4383
_reflns_number_gt                1113
_reflns_number_total             8726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1056888_si_001.cif
_cod_data_source_block           xws10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4102854
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
S1 S 1.3717(5) 1.9128(4) 0.7601(3) 0.0294(12) Uani 1 1 d .
S2 S 0.8368(5) 1.6774(4) 0.2194(3) 0.0281(12) Uani 1 1 d .
O1 O 0.8449(14) 1.6360(10) 0.6464(9) 0.053(4) Uani 1 1 d .
O2 O 1.4067(12) 1.7820(9) 0.7277(7) 0.039(3) Uani 1 1 d .
O3 O 1.4912(11) 2.0082(9) 0.7657(7) 0.033(3) Uani 1 1 d .
O4 O 0.9591(12) 1.5913(9) 0.1913(7) 0.036(3) Uani 1 1 d .
O5 O 0.8459(12) 1.8031(9) 0.2039(7) 0.037(3) Uani 1 1 d .
N1 N 1.2178(14) 1.9435(12) 0.6923(8) 0.029(3) Uani 1 1 d .
H1A H 1.2224 1.9990 0.6594 0.035 Uiso 1 1 calc R
N2 N 1.0820(16) 1.8750(11) 0.6919(9) 0.029(3) Uani 1 1 d .
N3 N 0.7690(14) 1.7930(11) 0.3747(10) 0.025(3) Uani 1 1 d .
N4 N 0.8515(15) 1.6880(11) 0.3276(8) 0.028(3) Uani 1 1 d .
H4B H 0.9042 1.6356 0.3549 0.034 Uiso 1 1 calc R
C1 C 0.807(3) 1.6555(17) 0.7409(12) 0.073(7) Uani 1 1 d .
H1B H 0.8676 1.5986 0.7720 0.110 Uiso 1 1 calc R
H1C H 0.6929 1.6394 0.7397 0.110 Uiso 1 1 calc R
H1D H 0.8359 1.7413 0.7722 0.110 Uiso 1 1 calc R
C2 C 1.1320(18) 1.9459(15) 1.1198(11) 0.040(5) Uani 1 1 d .
H2C H 1.1608 2.0274 1.1589 0.060 Uiso 1 1 calc R
H2D H 1.1806 1.8812 1.1480 0.060 Uiso 1 1 calc R
H2E H 1.0160 1.9329 1.1101 0.060 Uiso 1 1 calc R
C3 C 1.1931(18) 1.9396(16) 1.0287(12) 0.034(4) Uani 1 1 d .
C4 C 1.1647(18) 1.8297(15) 0.9610(12) 0.033(5) Uani 1 1 d .
H4C H 1.1065 1.7610 0.9705 0.040 Uiso 1 1 calc R
C5 C 1.2203(19) 1.8243(14) 0.8846(14) 0.040(5) Uani 1 1 d .
H5B H 1.2035 1.7492 0.8406 0.048 Uiso 1 1 calc R
C6 C 1.3044(17) 1.9253(14) 0.8644(11) 0.027(4) Uani 1 1 d .
C7 C 1.3314(17) 2.0315(15) 0.9364(12) 0.034(5) Uani 1 1 d .
H7A H 1.3914 2.1003 0.9284 0.041 Uiso 1 1 calc R
C8 C 1.2774(19) 2.0390(15) 1.0137(11) 0.032(4) Uani 1 1 d .
H8A H 1.2966 2.1128 1.0589 0.038 Uiso 1 1 calc R
C9 C 0.948(2) 1.9089(15) 0.6623(12) 0.036(5) Uani 1 1 d .
C10 C 0.8983(16) 2.0127(16) 0.6172(12) 0.038(5) Uani 1 1 d .
H10A H 0.9492 2.0125 0.5632 0.045 Uiso 1 1 calc R
H10B H 0.9114 2.0955 0.6581 0.045 Uiso 1 1 calc R
C11 C 0.724(2) 1.9610(15) 0.5960(11) 0.040(5) Uani 1 1 d .
H11A H 0.6483 2.0180 0.6271 0.048 Uiso 1 1 calc R
C12 C 0.6577(18) 1.9008(15) 0.5008(13) 0.046(5) Uani 1 1 d .
H12A H 0.6533 1.9653 0.4649 0.055 Uiso 1 1 calc R
H12B H 0.5470 1.8712 0.5000 0.055 Uiso 1 1 calc R
C13 C 0.747(2) 1.7937(14) 0.4550(12) 0.034(5) Uani 1 1 d .
C14 C 0.8066(17) 1.6971(13) 0.5088(10) 0.022(4) Uani 1 1 d .
H14A H 0.7652 1.6134 0.4761 0.027 Uiso 1 1 calc R
H14B H 0.9243 1.6973 0.5158 0.027 Uiso 1 1 calc R
C15 C 0.754(2) 1.7252(16) 0.5968(13) 0.048(5) Uani 1 1 d .
H15A H 0.6369 1.7055 0.5903 0.057 Uiso 1 1 calc R
C16 C 0.790(2) 1.8581(17) 0.6516(12) 0.046(5) Uani 1 1 d .
H16A H 0.7487 1.8703 0.7102 0.055 Uiso 1 1 calc R
C17 C 0.6514(17) 1.6078(14) 0.1711(11) 0.028(4) Uani 1 1 d .
C18 C 0.510(2) 1.6801(14) 0.1732(10) 0.035(5) Uani 1 1 d .
H18A H 0.5145 1.7659 0.2004 0.042 Uiso 1 1 calc R
C19 C 0.3664(18) 1.6175(12) 0.1332(10) 0.024(4) Uani 1 1 d .
H19A H 0.2727 1.6638 0.1323 0.028 Uiso 1 1 calc R
C20 C 0.3524(18) 1.4950(15) 0.0956(12) 0.034(5) Uani 1 1 d .
C21 C 0.488(2) 1.4261(14) 0.0924(11) 0.038(5) Uani 1 1 d .
H21A H 0.4794 1.3413 0.0624 0.046 Uiso 1 1 calc R
C22 C 0.6363(19) 1.4792(14) 0.1322(11) 0.034(4) Uani 1 1 d .
H22A H 0.7270 1.4296 0.1333 0.040 Uiso 1 1 calc R
C23 C 0.1898(19) 1.4296(14) 0.0507(11) 0.045(5) Uani 1 1 d .
H23A H 0.1053 1.4892 0.0582 0.068 Uiso 1 1 calc R
H23B H 0.1681 1.3608 0.0788 0.068 Uiso 1 1 calc R
H23C H 0.1937 1.3976 -0.0131 0.068 Uiso 1 1 calc R
Cl1 Cl 0.5480(7) 1.4311(6) 0.6165(5) 0.094(2) Uani 1 1 d .
Cl2 Cl 0.7414(7) 1.2570(6) 0.5057(4) 0.079(2) Uani 1 1 d .
O6 O 1.1672(13) 1.5706(9) 0.6590(7) 0.040(3) Uani 1 1 d .
C24 C 0.725(3) 1.3474(16) 0.6190(16) 0.114(11) Uani 1 1 d .
H24A H 0.7235 1.2909 0.6606 0.136 Uiso 1 1 calc R
H24B H 0.8183 1.4057 0.6404 0.136 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'
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'
Cl Cl 0.1484 0.1585 '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
O3 S1 O2 119.7(7)
O3 S1 N1 106.2(7)
O2 S1 N1 106.9(6)
O3 S1 C6 110.0(7)
O2 S1 C6 107.5(7)
N1 S1 C6 105.6(7)
O4 S2 O5 118.9(7)
O4 S2 N4 104.1(7)
O5 S2 N4 107.9(6)
O4 S2 C17 108.1(7)
O5 S2 C17 109.4(7)
N4 S2 C17 107.9(7)
C1 O1 C15 110.5(13)
N2 N1 S1 114.0(10)
C9 N2 N1 120.7(14)
C13 N3 N4 117.8(14)
N3 N4 S2 114.0(10)
C8 C3 C4 119.8(17)
C8 C3 C2 120.6(16)
C4 C3 C2 119.6(16)
C5 C4 C3 119.1(16)
C4 C5 C6 123.5(16)
C7 C6 C5 114.1(16)
C7 C6 S1 124.8(13)
C5 C6 S1 121.1(14)
C8 C7 C6 123.5(17)
C7 C8 C3 119.9(18)
N2 C9 C16 133.7(17)
N2 C9 C10 132.5(16)
C16 C9 C10 93.5(13)
C9 C10 C11 91.2(12)
C12 C11 C10 119.2(15)
C12 C11 C16 111.2(14)
C10 C11 C16 84.0(11)
C11 C12 C13 116.8(14)
N3 C13 C12 116.6(16)
N3 C13 C14 125.5(16)
C12 C13 C14 117.9(16)
C15 C14 C13 110.2(14)
C14 C15 O1 103.6(14)
C14 C15 C16 116.1(14)
O1 C15 C16 108.5(14)
C9 C16 C15 118.8(16)
C9 C16 C11 91.0(13)
C15 C16 C11 111.8(14)
C22 C17 C18 119.1(14)
C22 C17 S2 120.6(11)
C18 C17 S2 120.3(12)
C19 C18 C17 116.7(14)
C20 C19 C18 124.1(15)
C19 C20 C21 119.3(15)
C19 C20 C23 122.2(14)
C21 C20 C23 118.5(15)
C20 C21 C22 121.0(15)
C21 C22 C17 119.6(14)
Cl1 C24 Cl2 109.5(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.437(10)
S1 O2 1.472(11)
S1 N1 1.648(12)
S1 C6 1.761(17)
S2 O4 1.461(10)
S2 O5 1.461(10)
S2 N4 1.639(12)
S2 C17 1.745(16)
O1 C1 1.51(2)
O1 C15 1.530(19)
N1 N2 1.372(16)
N2 C9 1.261(18)
N3 C13 1.279(19)
N3 N4 1.469(16)
C2 C3 1.55(2)
C3 C8 1.38(2)
C3 C4 1.42(2)
C4 C5 1.32(2)
C5 C6 1.43(2)
C6 C7 1.43(2)
C7 C8 1.32(2)
C9 C16 1.42(2)
C9 C10 1.50(2)
C10 C11 1.55(2)
C11 C12 1.51(2)
C11 C16 1.63(2)
C12 C13 1.51(2)
C13 C14 1.54(2)
C14 C15 1.46(2)
C15 C16 1.54(2)
C17 C22 1.42(2)
C17 C18 1.45(2)
C18 C19 1.393(19)
C19 C20 1.35(2)
C20 C21 1.39(2)
C20 C23 1.56(2)
C21 C22 1.39(2)
Cl1 C24 1.77(2)
Cl2 C24 1.85(2)
