#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025649.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_4025649
loop_
_publ_author_name
'Andrei Poloukhtine'
'Valentin Rassadin'
'Alexander Kuzmin'
'Vladimir V. Popik'
_publ_section_title
;
 Nucleophilic Cycloaromatization of Ynamide-Terminated Enediynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5953
_journal_page_last               5962
_journal_paper_doi               10.1021/jo101238x
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C21 H21 N O4 S'
_chemical_formula_weight         383.45
_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                97.030(2)
_cell_angle_beta                 96.452(2)
_cell_angle_gamma                107.614(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8733(12)
_cell_length_b                   9.7887(15)
_cell_length_c                   13.227(2)
_cell_measurement_temperature    273(2)
_cell_volume                     952.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10229
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0366
_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)+(0.0635P)²+0.1877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2781
_reflns_number_total             3360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101238x_si_004.cif
_cod_data_source_block           uga601
_cod_database_code               4025649
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 0.18683(6) 0.55234(5) 0.30728(4) 0.05145(18) Uani 1 1 d . . .
N1 N 0.30483(18) 0.70464(16) 0.38068(11) 0.0488(4) Uani 1 1 d . . .
O1 O 0.82725(16) 0.71945(15) 0.49589(11) 0.0571(4) Uani 1 1 d . . .
H1B H 0.835(3) 0.669(3) 0.5439(18) 0.078(7) Uiso 1 1 d . . .
O2 O 0.95058(17) 0.92018(16) 0.39349(11) 0.0635(4) Uani 1 1 d . . .
H2C H 0.948(3) 0.861(3) 0.4392(19) 0.085(8) Uiso 1 1 d . . .
O3 O 0.09163(18) 0.46163(14) 0.37373(11) 0.0660(4) Uani 1 1 d . . .
O4 O 0.30452(19) 0.50387(15) 0.24871(13) 0.0731(4) Uani 1 1 d . . .
C1 C 0.6442(2) 0.71598(17) 0.47442(13) 0.0422(4) Uani 1 1 d . . .
H1A H 0.5702 0.6156 0.4459 0.051 Uiso 1 1 calc R . .
C2 C 0.5771(2) 0.76194(19) 0.57260(13) 0.0498(4) Uani 1 1 d . . .
H2A H 0.6343 0.7293 0.6295 0.060 Uiso 1 1 calc R . .
H2B H 0.6151 0.8672 0.5871 0.060 Uiso 1 1 calc R . .
C3 C 0.3735(2) 0.7036(2) 0.56818(14) 0.0527(4) Uani 1 1 d . . .
H3A H 0.3369 0.5983 0.5589 0.063 Uiso 1 1 calc R . .
H3B H 0.3442 0.7373 0.6340 0.063 Uiso 1 1 calc R . .
C4 C 0.2648(2) 0.7468(2) 0.48381(15) 0.0555(5) Uani 1 1 d . . .
H4A H 0.1374 0.7013 0.4851 0.067 Uiso 1 1 calc R . .
H4B H 0.2901 0.8512 0.4971 0.067 Uiso 1 1 calc R . .
C5 C 0.4557(2) 0.80152(17) 0.34586(13) 0.0452(4) Uani 1 1 d . . .
C6 C 0.6309(2) 0.80945(16) 0.39173(12) 0.0408(4) Uani 1 1 d . . .
C7 C 0.7760(2) 0.90211(18) 0.35831(13) 0.0458(4) Uani 1 1 d . . .
C8 C 0.7501(3) 0.98558(18) 0.28032(13) 0.0524(5) Uani 1 1 d . . .
C9 C 0.8979(3) 1.0800(2) 0.24612(16) 0.0714(6) Uani 1 1 d . . .
H9A H 1.0148 1.0864 0.2732 0.086 Uiso 1 1 calc R . .
C10 C 0.8709(4) 1.1618(3) 0.17370(18) 0.0921(8) Uani 1 1 d . . .
H10A H 0.9696 1.2249 0.1525 0.110 Uiso 1 1 calc R . .
C11 C 0.6973(4) 1.1520(3) 0.13109(19) 0.0956(9) Uani 1 1 d . . .
H11A H 0.6809 1.2077 0.0810 0.115 Uiso 1 1 calc R . .
C12 C 0.5515(4) 1.0623(2) 0.16178(17) 0.0791(7) Uani 1 1 d . . .
H12A H 0.4361 1.0570 0.1327 0.095 Uiso 1 1 calc R . .
C13 C 0.5737(3) 0.97598(19) 0.23810(14) 0.0564(5) Uani 1 1 d . . .
C14 C 0.4266(3) 0.8830(2) 0.27357(15) 0.0563(5) Uani 1 1 d . . .
H14A H 0.3094 0.8773 0.2476 0.068 Uiso 1 1 calc R . .
C15 C 0.0242(2) 0.58632(18) 0.22081(13) 0.0451(4) Uani 1 1 d . . .
C16 C -0.1420(2) 0.5784(2) 0.24656(14) 0.0536(4) Uani 1 1 d . . .
H16A H -0.1715 0.5502 0.3087 0.064 Uiso 1 1 calc R . .
C17 C -0.2656(3) 0.6126(2) 0.17999(15) 0.0637(5) Uani 1 1 d . . .
H17A H -0.3786 0.6057 0.1977 0.076 Uiso 1 1 calc R . .
C18 C -0.2254(3) 0.6561(2) 0.08889(16) 0.0674(6) Uani 1 1 d . . .
C19 C -0.0597(4) 0.6602(3) 0.06352(17) 0.0847(7) Uani 1 1 d . . .
H19A H -0.0311 0.6874 0.0010 0.102 Uiso 1 1 calc R . .
C20 C 0.0648(3) 0.6255(3) 0.12744(16) 0.0720(6) Uani 1 1 d . . .
H20A H 0.1756 0.6284 0.1081 0.086 Uiso 1 1 calc R . .
C21 C -0.3583(5) 0.7008(3) 0.0190(2) 0.1093(10) Uani 1 1 d . . .
H21C H -0.4662 0.6904 0.0489 0.164 Uiso 1 1 calc R . .
H21D H -0.3875 0.6399 -0.0473 0.164 Uiso 1 1 calc R . .
H21A H -0.3053 0.8003 0.0112 0.164 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'
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
O4 S1 O3 119.44(9) . . ?
O4 S1 N1 107.81(8) . . ?
O3 S1 N1 106.05(8) . . ?
O4 S1 C15 107.79(9) . . ?
O3 S1 C15 107.08(8) . . ?
N1 S1 C15 108.25(8) . . ?
C5 N1 C4 118.25(15) . . ?
C5 N1 S1 119.72(12) . . ?
C4 N1 S1 122.02(12) . . ?
O1 C1 C6 108.10(13) . . ?
O1 C1 C2 111.10(14) . . ?
C6 C1 C2 113.54(13) . . ?
C3 C2 C1 114.60(14) . . ?
C4 C3 C2 115.01(15) . . ?
N1 C4 C3 112.60(14) . . ?
C14 C5 C6 122.90(17) . . ?
C14 C5 N1 119.86(16) . . ?
C6 C5 N1 117.22(14) . . ?
C7 C6 C5 117.33(15) . . ?
C7 C6 C1 125.19(15) . . ?
C5 C6 C1 117.48(14) . . ?
O2 C7 C6 124.33(15) . . ?
O2 C7 C8 114.49(15) . . ?
C6 C7 C8 121.17(16) . . ?
C13 C8 C9 119.24(18) . . ?
C13 C8 C7 119.55(17) . . ?
C9 C8 C7 121.21(19) . . ?
C10 C9 C8 120.4(2) . . ?
C9 C10 C11 120.6(2) . . ?
C12 C11 C10 120.7(2) . . ?
C11 C12 C13 120.5(2) . . ?
C8 C13 C14 119.00(16) . . ?
C8 C13 C12 118.5(2) . . ?
C14 C13 C12 122.5(2) . . ?
C5 C14 C13 120.00(18) . . ?
C16 C15 C20 119.46(17) . . ?
C16 C15 S1 120.41(13) . . ?
C20 C15 S1 120.10(15) . . ?
C15 C16 C17 119.82(17) . . ?
C18 C17 C16 121.45(19) . . ?
C17 C18 C19 117.79(19) . . ?
C17 C18 C21 121.0(2) . . ?
C19 C18 C21 121.2(2) . . ?
C18 C19 C20 122.1(2) . . ?
C19 C20 C15 119.4(2) . . ?
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 O4 1.4217(14) . ?
S1 O3 1.4350(14) . ?
S1 N1 1.6227(15) . ?
S1 C15 1.7551(17) . ?
N1 C5 1.439(2) . ?
N1 C4 1.472(2) . ?
O1 C1 1.4262(19) . ?
O2 C7 1.352(2) . ?
C1 C6 1.524(2) . ?
C1 C2 1.524(2) . ?
C2 C3 1.522(3) . ?
C3 C4 1.509(3) . ?
C5 C14 1.361(2) . ?
C5 C6 1.419(2) . ?
C6 C7 1.381(2) . ?
C7 C8 1.426(2) . ?
C8 C13 1.408(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.360(3) . ?
C10 C11 1.389(4) . ?
C11 C12 1.355(4) . ?
C12 C13 1.422(3) . ?
C13 C14 1.407(3) . ?
C15 C16 1.371(2) . ?
C15 C20 1.380(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.365(3) . ?
C18 C19 1.373(3) . ?
C18 C21 1.516(3) . ?
C19 C20 1.370(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1B O3 0.86(2) 1.95(3) 2.7766(18) 161(2) 2_666
