#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023942.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_4023942
loop_
_publ_author_name
'Yu-Long Zhao'
'Wei Zhang'
'Shuang Wang'
'Qun Liu'
_publ_section_title
;
 Ethynyl Ketene-S,S-acetals: The Highly Reactive Electron-Rich
 Dienophiles and Applications in the Synthesis of 4-Functionalized
 Quinolines via a One-Pot Three-Component Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4985
_journal_page_last               4988
_journal_paper_doi               10.1021/jo070069q
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C24 H22 N2 O4 S2'
_chemical_formula_weight         466.58
_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                69.052(7)
_cell_angle_beta                 83.860(7)
_cell_angle_gamma                73.520(7)
_cell_formula_units_Z            2
_cell_length_a                   9.616(4)
_cell_length_b                   11.270(5)
_cell_length_c                   11.587(5)
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.88
_cell_volume                     1124.5(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 0.01
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6497
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488.0
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0810P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1649
_reflns_number_gt                2671
_reflns_number_total             4440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070069qsi20070112_015637.cif
_cod_data_source_block           ds
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C24 H22 N2 O4 S2 '
_cod_database_code               4023942
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 0.20806(11) 0.18586(9) 0.80837(8) 0.0544(3) Uani 1 1 d . . .
S2 S 0.23718(11) -0.09200(9) 0.97906(9) 0.0572(3) Uani 1 1 d . . .
C1 C 0.2207(5) -0.0831(5) 0.8207(4) 0.0679(12) Uani 1 1 d . . .
H1A H 0.222(4) -0.175(4) 0.834(3) 0.059(10) Uiso 1 1 d . . .
H1B H 0.319(6) -0.067(5) 0.770(4) 0.124(18) Uiso 1 1 d . . .
C2 C 0.0872(6) 0.0135(5) 0.7533(6) 0.0843(15) Uani 1 1 d . . .
C3 C 0.0553(4) 0.1456(4) 0.7675(4) 0.0600(11) Uani 1 1 d . . .
H3A H 0.013(4) 0.212(4) 0.697(4) 0.069(12) Uiso 1 1 d . . .
H3B H -0.016(4) 0.153(4) 0.837(4) 0.081(13) Uiso 1 1 d . . .
C4 C 0.2496(3) 0.0677(3) 0.9559(3) 0.0424(8) Uani 1 1 d . . .
C5 C 0.2907(3) 0.1024(3) 1.0465(3) 0.0410(8) Uani 1 1 d . . .
C6 C 0.3343(4) 0.0016(4) 1.1680(3) 0.0484(9) Uani 1 1 d . . .
C7 C 0.4327(5) -0.0516(5) 1.3647(4) 0.0660(11) Uani 1 1 d . . .
H7B H 0.493(4) -0.008(4) 1.392(3) 0.070(12) Uiso 1 1 d . . .
H7A H 0.491(4) -0.137(4) 1.361(3) 0.076(13) Uiso 1 1 d . . .
C8 C 0.3042(7) -0.0662(7) 1.4469(5) 0.0840(15) Uani 1 1 d . . .
H8C H 0.255(6) -0.118(5) 1.422(5) 0.12(2) Uiso 1 1 d . . .
H8B H 0.251(6) 0.009(6) 1.460(5) 0.13(2) Uiso 1 1 d . . .
H8A H 0.334(5) -0.119(4) 1.528(5) 0.099(16) Uiso 1 1 d . . .
C9 C 0.2935(3) 0.2408(3) 1.0216(3) 0.0406(8) Uani 1 1 d . . .
C10 C 0.1983(3) 0.3218(3) 1.0835(3) 0.0388(7) Uani 1 1 d . . .
C11 C 0.1004(4) 0.2772(3) 1.1787(3) 0.0431(8) Uani 1 1 d . . .
H11 H 0.099(3) 0.189(3) 1.197(2) 0.032(8) Uiso 1 1 d . . .
C12 C 0.0148(3) 0.3561(3) 1.2393(3) 0.0469(8) Uani 1 1 d . . .
C13 C 0.0226(4) 0.4878(4) 1.2029(3) 0.0538(10) Uani 1 1 d . . .
H13 H -0.039(4) 0.541(3) 1.245(3) 0.063(11) Uiso 1 1 d . . .
C14 C 0.1122(4) 0.5355(4) 1.1102(3) 0.0508(9) Uani 1 1 d . . .
H14 H 0.121(4) 0.616(4) 1.084(3) 0.066(12) Uiso 1 1 d . . .
C15 C 0.2031(3) 0.4554(3) 1.0472(3) 0.0401(8) Uani 1 1 d . . .
C16 C 0.3837(4) 0.2970(3) 0.9329(3) 0.0435(8) Uani 1 1 d . . .
H16 H 0.446(3) 0.244(3) 0.900(2) 0.027(8) Uiso 1 1 d . . .
C17 C 0.3790(3) 0.4318(3) 0.9000(3) 0.0419(8) Uani 1 1 d . . .
C18 C -0.0879(5) 0.3064(5) 1.3407(5) 0.0648(12) Uani 1 1 d . . .
H18B H -0.086(5) 0.330(4) 1.407(4) 0.096(17) Uiso 1 1 d . . .
H18A H -0.064(5) 0.218(5) 1.370(4) 0.099(18) Uiso 1 1 d . . .
H18C H -0.194(6) 0.352(5) 1.308(5) 0.126(19) Uiso 1 1 d . . .
C19 C 0.4749(4) 0.4919(3) 0.7990(3) 0.0451(8) Uani 1 1 d . . .
C20 C 0.5404(5) 0.4311(4) 0.7147(4) 0.0707(13) Uani 1 1 d . . .
H20 H 0.521(4) 0.356(4) 0.710(3) 0.072(12) Uiso 1 1 d . . .
C21 C 0.6318(5) 0.4859(4) 0.6236(4) 0.0778(14) Uani 1 1 d . . .
H21 H 0.676(4) 0.444(4) 0.566(3) 0.073(12) Uiso 1 1 d . . .
C22 C 0.6555(4) 0.6028(4) 0.6159(3) 0.0555(10) Uani 1 1 d . . .
C23 C 0.5910(4) 0.6652(4) 0.6970(3) 0.0517(10) Uani 1 1 d . . .
H23 H 0.602(4) 0.739(3) 0.691(3) 0.055(11) Uiso 1 1 d . . .
C24 C 0.5002(4) 0.6113(3) 0.7889(3) 0.0454(8) Uani 1 1 d . . .
H24 H 0.455(4) 0.652(3) 0.854(3) 0.063(11) Uiso 1 1 d . . .
O1 O 0.3207(3) -0.1104(2) 1.2010(2) 0.0706(8) Uani 1 1 d . . .
O2 O 0.3929(3) 0.0441(2) 1.2421(2) 0.0540(6) Uani 1 1 d . . .
O3 O 0.8285(4) 0.5926(3) 0.4632(3) 0.1155(14) Uani 1 1 d . . .
O4 O 0.7630(3) 0.7697(3) 0.5072(3) 0.0837(9) Uani 1 1 d . . .
N1 N 0.2914(3) 0.5087(2) 0.9553(2) 0.0434(7) Uani 1 1 d . . .
N2 N 0.7560(4) 0.6582(4) 0.5223(3) 0.0675(9) Uani 1 1 d . . .
H2B H -0.004(7) -0.033(6) 0.808(6) 0.18(3) Uiso 1 1 d . . .
H2A H 0.076(7) 0.019(6) 0.676(6) 0.16(3) 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
C4 S1 C3 101.45(19) . . ?
C4 S2 C1 101.37(18) . . ?
C2 C1 S2 115.6(3) . . ?
C2 C1 H1A 112(2) . . ?
S2 C1 H1A 101(2) . . ?
C2 C1 H1B 112(3) . . ?
S2 C1 H1B 109(3) . . ?
H1A C1 H1B 106(3) . . ?
C3 C2 C1 113.5(4) . . ?
C3 C2 H2B 105(3) . . ?
C1 C2 H2B 102(3) . . ?
C3 C2 H2A 113(4) . . ?
C1 C2 H2A 117(4) . . ?
H2B C2 H2A 104(5) . . ?
C2 C3 S1 115.7(3) . . ?
C2 C3 H3A 111(2) . . ?
S1 C3 H3A 109(2) . . ?
C2 C3 H3B 112(2) . . ?
S1 C3 H3B 103(2) . . ?
H3A C3 H3B 106(3) . . ?
C5 C4 S1 119.4(2) . . ?
C5 C4 S2 123.3(3) . . ?
S1 C4 S2 117.22(19) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C9 120.4(3) . . ?
C6 C5 C9 120.1(3) . . ?
O1 C6 O2 122.1(3) . . ?
O1 C6 C5 124.4(3) . . ?
O2 C6 C5 113.5(3) . . ?
O2 C7 C8 112.2(4) . . ?
O2 C7 H7B 100(2) . . ?
C8 C7 H7B 111(2) . . ?
O2 C7 H7A 112(2) . . ?
C8 C7 H7A 111(2) . . ?
H7B C7 H7A 110(3) . . ?
C7 C8 H8C 108(3) . . ?
C7 C8 H8B 115(4) . . ?
H8C C8 H8B 119(5) . . ?
C7 C8 H8A 110(3) . . ?
H8C C8 H8A 104(4) . . ?
H8B C8 H8A 100(4) . . ?
C16 C9 C10 117.4(3) . . ?
C16 C9 C5 120.4(3) . . ?
C10 C9 C5 122.1(3) . . ?
C11 C10 C15 118.3(3) . . ?
C11 C10 C9 124.0(3) . . ?
C15 C10 C9 117.7(3) . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 122.5(17) . . ?
C10 C11 H11 115.0(17) . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 C18 121.5(4) . . ?
C13 C12 C18 120.2(3) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 122(2) . . ?
C12 C13 H13 117(2) . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 125(2) . . ?
C15 C14 H14 113(2) . . ?
N1 C15 C14 118.8(3) . . ?
N1 C15 C10 123.0(3) . . ?
C14 C15 C10 118.2(3) . . ?
C9 C16 C17 121.3(3) . . ?
C9 C16 H16 116.0(18) . . ?
C17 C16 H16 122.6(18) . . ?
N1 C17 C16 122.3(3) . . ?
N1 C17 C19 117.6(3) . . ?
C16 C17 C19 120.1(3) . . ?
C12 C18 H18B 114(3) . . ?
C12 C18 H18A 111(3) . . ?
H18B C18 H18A 105(4) . . ?
C12 C18 H18C 109(3) . . ?
H18B C18 H18C 104(4) . . ?
H18A C18 H18C 115(4) . . ?
C20 C19 C24 118.9(3) . . ?
C20 C19 C17 121.3(3) . . ?
C24 C19 C17 119.8(3) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 115(2) . . ?
C19 C20 H20 124(2) . . ?
C22 C21 C20 119.3(4) . . ?
C22 C21 H21 120(2) . . ?
C20 C21 H21 121(2) . . ?
C21 C22 C23 121.0(4) . . ?
C21 C22 N2 119.1(4) . . ?
C23 C22 N2 119.8(4) . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 121(2) . . ?
C24 C23 H23 118(2) . . ?
C23 C24 C19 119.6(4) . . ?
C23 C24 H24 123(2) . . ?
C19 C24 H24 117(2) . . ?
C6 O2 C7 115.0(3) . . ?
C17 N1 C15 118.2(3) . . ?
O3 N2 O4 122.8(3) . . ?
O3 N2 C22 119.0(4) . . ?
O4 N2 C22 118.1(4) . . ?
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 C4 1.753(3) . ?
S1 C3 1.808(4) . ?
S2 C4 1.759(3) . ?
S2 C1 1.823(4) . ?
C1 C2 1.503(7) . ?
C1 H1A 0.98(4) . ?
C1 H1B 1.08(5) . ?
C2 C3 1.498(6) . ?
C2 H2B 1.16(7) . ?
C2 H2A 0.89(6) . ?
C3 H3A 0.93(4) . ?
C3 H3B 1.01(4) . ?
C4 C5 1.372(4) . ?
C5 C6 1.470(5) . ?
C5 C9 1.488(4) . ?
C6 O1 1.223(4) . ?
C6 O2 1.354(4) . ?
C7 O2 1.454(4) . ?
C7 C8 1.487(7) . ?
C7 H7B 0.99(4) . ?
C7 H7A 0.98(4) . ?
C8 H8C 0.98(5) . ?
C8 H8B 0.91(6) . ?
C8 H8A 0.94(5) . ?
C9 C16 1.366(4) . ?
C9 C10 1.429(4) . ?
C10 C11 1.416(4) . ?
C10 C15 1.424(4) . ?
C11 C12 1.368(4) . ?
C11 H11 0.94(3) . ?
C12 C13 1.412(5) . ?
C12 C18 1.505(5) . ?
C13 C14 1.355(5) . ?
C13 H13 0.95(4) . ?
C14 C15 1.414(5) . ?
C14 H14 0.88(4) . ?
C15 N1 1.362(4) . ?
C16 C17 1.416(4) . ?
C16 H16 0.88(3) . ?
C17 N1 1.319(4) . ?
C17 C19 1.495(4) . ?
C18 H18B 0.90(4) . ?
C18 H18A 0.90(5) . ?
C18 H18C 1.05(6) . ?
C19 C20 1.386(5) . ?
C19 C24 1.397(4) . ?
C20 C21 1.383(5) . ?
C20 H20 0.94(4) . ?
C21 C22 1.370(5) . ?
C21 H21 0.94(4) . ?
C22 C23 1.364(5) . ?
C22 N2 1.460(5) . ?
C23 C24 1.380(5) . ?
C23 H23 0.84(3) . ?
C24 H24 1.01(3) . ?
O3 N2 1.212(4) . ?
O4 N2 1.226(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20564045
