#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025650.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_4025650
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            'C27 H23 N O2 S'
_chemical_formula_weight         425.52
_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                92.826(2)
_cell_angle_beta                 110.953(2)
_cell_angle_gamma                102.671(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0169(14)
_cell_length_b                   11.4036(18)
_cell_length_c                   12.0895(19)
_cell_measurement_temperature    273(2)
_cell_volume                     1121.4(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15601
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0528
_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)+(0.0901P)²+0.1475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1707
_reflns_number_gt                3501
_reflns_number_total             5568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101238x_si_005.cif
_cod_data_source_block           uga640
_cod_database_code               4025650
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 0.35404(7) 0.32495(5) 0.10107(5) 0.05020(18) Uani 1 1 d . . .
O1 O 0.20807(19) 0.23544(16) 0.08758(14) 0.0627(5) Uani 1 1 d . . .
O2 O 0.3482(2) 0.41291(17) 0.02091(15) 0.0698(5) Uani 1 1 d . . .
N1 N 0.4224(2) 0.40012(16) 0.23549(16) 0.0480(4) Uani 1 1 d . . .
C1 C 0.5401(3) 0.5201(2) 0.2664(2) 0.0616(6) Uani 1 1 d . . .
H1A H 0.5409 0.5605 0.3392 0.074 Uiso 1 1 calc R . .
H1B H 0.5020 0.5684 0.2032 0.074 Uiso 1 1 calc R . .
C2 C 0.7130(3) 0.5174(2) 0.2844(3) 0.0665(7) Uani 1 1 d . . .
H2A H 0.7166 0.4956 0.2070 0.080 Uiso 1 1 calc R . .
H2B H 0.7835 0.5986 0.3160 0.080 Uiso 1 1 calc R . .
C3 C 0.7812(3) 0.4325(2) 0.3654(2) 0.0585(6) Uani 1 1 d . . .
H3A H 0.8903 0.4353 0.3795 0.070 Uiso 1 1 calc R . .
C4 C 0.7131(3) 0.3530(2) 0.4215(2) 0.0543(6) Uani 1 1 d . . .
H4A H 0.7840 0.3105 0.4679 0.065 Uiso 1 1 calc R . .
C5 C 0.5476(2) 0.31928(19) 0.42458(18) 0.0430(5) Uani 1 1 d . . .
C6 C 0.4053(2) 0.33893(18) 0.33233(17) 0.0423(5) Uani 1 1 d . . .
C7 C 0.2537(2) 0.3028(2) 0.33619(19) 0.0470(5) Uani 1 1 d . . .
H7A H 0.1645 0.3176 0.2754 0.056 Uiso 1 1 calc R . .
C8 C 0.2276(2) 0.24401(19) 0.42906(19) 0.0448(5) Uani 1 1 d . . .
C9 C 0.0689(3) 0.2080(2) 0.4337(2) 0.0558(6) Uani 1 1 d . . .
H9A H -0.0214 0.2200 0.3718 0.067 Uiso 1 1 calc R . .
C10 C 0.0479(3) 0.1564(2) 0.5274(3) 0.0647(7) Uani 1 1 d . . .
H10A H -0.0565 0.1333 0.5295 0.078 Uiso 1 1 calc R . .
C11 C 0.1827(3) 0.1376(3) 0.6209(3) 0.0661(7) Uani 1 1 d . . .
H11A H 0.1672 0.1028 0.6852 0.079 Uiso 1 1 calc R . .
C12 C 0.3362(3) 0.1698(2) 0.6191(2) 0.0567(6) Uani 1 1 d . . .
H12A H 0.4241 0.1569 0.6824 0.068 Uiso 1 1 calc R . .
C13 C 0.3648(2) 0.22265(19) 0.52230(18) 0.0439(5) Uani 1 1 d . . .
C14 C 0.5243(2) 0.26103(19) 0.51836(18) 0.0440(5) Uani 1 1 d . . .
C15 C 0.6673(2) 0.2401(2) 0.61864(18) 0.0475(5) Uani 1 1 d . . .
C16 C 0.6842(3) 0.1237(2) 0.6351(2) 0.0634(7) Uani 1 1 d . . .
H16A H 0.6069 0.0579 0.5819 0.076 Uiso 1 1 calc R . .
C17 C 0.8145(3) 0.1038(3) 0.7295(2) 0.0741(8) Uani 1 1 d . . .
H17A H 0.8238 0.0250 0.7394 0.089 Uiso 1 1 calc R . .
C18 C 0.9283(3) 0.1986(3) 0.8074(2) 0.0769(9) Uani 1 1 d . . .
H18A H 1.0157 0.1850 0.8706 0.092 Uiso 1 1 calc R . .
C19 C 0.9150(3) 0.3138(3) 0.7933(2) 0.0751(8) Uani 1 1 d . . .
H19A H 0.9940 0.3784 0.8471 0.090 Uiso 1 1 calc R . .
C20 C 0.7841(3) 0.3369(3) 0.6989(2) 0.0612(6) Uani 1 1 d . . .
H20A H 0.7758 0.4160 0.6903 0.073 Uiso 1 1 calc R . .
C21 C 0.4985(3) 0.24585(19) 0.09530(18) 0.0474(5) Uani 1 1 d . . .
C22 C 0.6064(3) 0.2883(2) 0.0406(2) 0.0645(7) Uani 1 1 d . . .
H22A H 0.6013 0.3578 0.0039 0.077 Uiso 1 1 calc R . .
C23 C 0.7219(4) 0.2265(3) 0.0408(3) 0.0693(7) Uani 1 1 d . . .
H23A H 0.7950 0.2560 0.0044 0.083 Uiso 1 1 calc R . .
C24 C 0.7326(3) 0.1225(2) 0.0933(2) 0.0572(6) Uani 1 1 d . . .
C25 C 0.6231(3) 0.0821(2) 0.1476(2) 0.0603(6) Uani 1 1 d . . .
H25A H 0.6282 0.0124 0.1841 0.072 Uiso 1 1 calc R . .
C26 C 0.5068(3) 0.1420(2) 0.1492(2) 0.0548(6) Uani 1 1 d . . .
H26A H 0.4344 0.1129 0.1862 0.066 Uiso 1 1 calc R . .
C27 C 0.8574(3) 0.0551(3) 0.0914(3) 0.0772(8) Uani 1 1 d . . .
H27B H 0.8462 -0.0144 0.1323 0.116 Uiso 1 1 calc R . .
H27C H 0.9657 0.1076 0.1307 0.116 Uiso 1 1 calc R . .
H27D H 0.8402 0.0290 0.0100 0.116 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'
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'
N N 0.0061 0.0033 '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 120.01(11) . . ?
O2 S1 N1 106.68(10) . . ?
O1 S1 N1 106.84(10) . . ?
O2 S1 C21 108.45(11) . . ?
O1 S1 C21 106.63(11) . . ?
N1 S1 C21 107.69(10) . . ?
C6 N1 C1 117.19(18) . . ?
C6 N1 S1 120.08(14) . . ?
C1 N1 S1 120.63(16) . . ?
N1 C1 C2 114.8(2) . . ?
C3 C2 C1 115.4(2) . . ?
C4 C3 C2 131.1(2) . . ?
C3 C4 C5 132.6(2) . . ?
C14 C5 C6 117.63(18) . . ?
C14 C5 C4 119.31(18) . . ?
C6 C5 C4 123.01(19) . . ?
C7 C6 N1 118.63(17) . . ?
C7 C6 C5 121.31(19) . . ?
N1 C6 C5 120.04(18) . . ?
C6 C7 C8 121.92(18) . . ?
C7 C8 C9 121.73(19) . . ?
C7 C8 C13 118.75(19) . . ?
C9 C8 C13 119.5(2) . . ?
C10 C9 C8 120.7(2) . . ?
C9 C10 C11 120.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C11 C12 C13 121.3(2) . . ?
C12 C13 C8 117.46(19) . . ?
C12 C13 C14 123.16(19) . . ?
C8 C13 C14 119.28(19) . . ?
C5 C14 C13 121.10(18) . . ?
C5 C14 C15 120.45(18) . . ?
C13 C14 C15 118.44(19) . . ?
C16 C15 C20 118.5(2) . . ?
C16 C15 C14 120.8(2) . . ?
C20 C15 C14 120.6(2) . . ?
C15 C16 C17 121.0(3) . . ?
C18 C17 C16 120.2(3) . . ?
C17 C18 C19 120.0(2) . . ?
C18 C19 C20 121.1(3) . . ?
C15 C20 C19 119.1(3) . . ?
C26 C21 C22 119.8(2) . . ?
C26 C21 S1 119.51(18) . . ?
C22 C21 S1 120.65(18) . . ?
C23 C22 C21 119.4(2) . . ?
C22 C23 C24 122.1(2) . . ?
C25 C24 C23 117.3(2) . . ?
C25 C24 C27 121.1(2) . . ?
C23 C24 C27 121.5(2) . . ?
C24 C25 C26 122.0(2) . . ?
C21 C26 C25 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 O2 1.4250(17) . ?
S1 O1 1.4289(17) . ?
S1 N1 1.6339(19) . ?
S1 C21 1.758(2) . ?
N1 C6 1.429(3) . ?
N1 C1 1.472(3) . ?
C1 C2 1.503(4) . ?
C2 C3 1.482(4) . ?
C3 C4 1.332(3) . ?
C4 C5 1.471(3) . ?
C5 C14 1.398(3) . ?
C5 C6 1.438(3) . ?
C6 C7 1.357(3) . ?
C7 C8 1.400(3) . ?
C8 C9 1.422(3) . ?
C8 C13 1.422(3) . ?
C9 C10 1.354(3) . ?
C10 C11 1.399(4) . ?
C11 C12 1.360(3) . ?
C12 C13 1.420(3) . ?
C13 C14 1.427(3) . ?
C14 C15 1.495(3) . ?
C15 C16 1.385(3) . ?
C15 C20 1.386(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.353(4) . ?
C18 C19 1.358(4) . ?
C19 C20 1.402(4) . ?
C21 C26 1.383(3) . ?
C21 C22 1.380(3) . ?
C22 C23 1.379(4) . ?
C23 C24 1.378(4) . ?
C24 C25 1.382(3) . ?
C24 C27 1.502(4) . ?
C25 C26 1.376(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659257
