# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Zhao, Yu-long'
_publ_contact_author_email       zhaoyl351@nenu.edu.cn

_publ_section_title              
;
Highly efficient synthesis of
3-amino-/alkylthio-cyclobut-2-en-1-ones based
on the intramolecular Michael addition of acyl ketene dithioacetals
;
_publ_author_name                'Yu-long Zhao'

# Attachment '4a1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 781521'
#TrackingRef '4a1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   4.9255(7)
_cell_length_b                   19.517(3)
_cell_length_c                   13.661(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.474(2)
_cell_angle_gamma                90.00
_cell_volume                     1310.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2296
_cell_measurement_theta_min      1.25
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6523
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2296
_reflns_number_gt                1266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.1270P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000

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 0.3889(6) 0.17116(14) 0.58958(19) 0.0500(7) Uani 1 1 d . . .
H1 H 0.3910 0.1753 0.5218 0.060 Uiso 1 1 calc R . .
C2 C 0.5563(6) 0.12488(14) 0.6387(2) 0.0538(8) Uani 1 1 d . . .
H2 H 0.6726 0.0981 0.6035 0.065 Uiso 1 1 calc R . .
C3 C 0.5565(6) 0.11687(13) 0.7406(2) 0.0515(7) Uani 1 1 d . . .
C4 C 0.3870(6) 0.15782(14) 0.79046(19) 0.0483(7) Uani 1 1 d . . .
H4 H 0.3870 0.1536 0.8583 0.058 Uiso 1 1 calc R . .
C5 C 0.2128(5) 0.20605(13) 0.74320(17) 0.0400(6) Uani 1 1 d . . .
C6 C 0.2157(5) 0.21200(13) 0.64146(17) 0.0389(6) Uani 1 1 d . . .
C7 C 0.0361(5) 0.25052(14) 0.79725(17) 0.0442(7) Uani 1 1 d . . .
C8 C -0.1265(5) 0.29913(13) 0.74104(17) 0.0397(6) Uani 1 1 d . . .
C9 C -0.1193(5) 0.30102(13) 0.63969(17) 0.0398(6) Uani 1 1 d . . .
C10 C -0.2720(6) 0.35145(14) 0.57379(18) 0.0538(8) Uani 1 1 d . . .
H10A H -0.4570 0.3555 0.5937 0.065 Uiso 1 1 calc R . .
H10B H -0.2799 0.3344 0.5070 0.065 Uiso 1 1 calc R . .
C11 C -0.1398(8) 0.42142(17) 0.5770(3) 0.0884(12) Uani 1 1 d . . .
H11A H -0.1362 0.4390 0.6427 0.133 Uiso 1 1 calc R . .
H11B H -0.2420 0.4519 0.5337 0.133 Uiso 1 1 calc R . .
H11C H 0.0428 0.4177 0.5566 0.133 Uiso 1 1 calc R . .
C12 C -0.2884(6) 0.35115(15) 0.79173(18) 0.0476(7) Uani 1 1 d . . .
C13 C -0.1515(6) 0.38870(16) 0.8778(2) 0.0631(9) Uani 1 1 d . . .
H13A H -0.1582 0.3603 0.9359 0.076 Uiso 1 1 calc R . .
H13B H 0.0383 0.3958 0.8654 0.076 Uiso 1 1 calc R . .
C14 C -0.2796(7) 0.45692(16) 0.8975(2) 0.0754(10) Uani 1 1 d . . .
H14A H -0.2501 0.4877 0.8443 0.113 Uiso 1 1 calc R . .
H14B H -0.1991 0.4756 0.9574 0.113 Uiso 1 1 calc R . .
H14C H -0.4715 0.4510 0.9033 0.113 Uiso 1 1 calc R . .
C15 C 0.7371(7) 0.06412(16) 0.7917(2) 0.0743(10) Uani 1 1 d . . .
H15A H 0.7376 0.0708 0.8614 0.111 Uiso 1 1 calc R . .
H15B H 0.9189 0.0688 0.7710 0.111 Uiso 1 1 calc R . .
H15C H 0.6699 0.0191 0.7755 0.111 Uiso 1 1 calc R . .
H1A H 0.044(5) 0.2617(13) 0.524(2) 0.062(8) Uiso 1 1 d . . .
N1 N 0.0453(4) 0.25887(11) 0.59305(15) 0.0410(6) Uani 1 1 d . . .
O1 O 0.0272(4) 0.24481(10) 0.88863(12) 0.0634(6) Uani 1 1 d . . .
O2 O -0.5197(4) 0.36611(11) 0.76291(16) 0.0739(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0595(18) 0.0563(17) 0.0347(15) -0.0043(13) 0.0070(14) -0.0009(15)
C2 0.0588(18) 0.0512(17) 0.0519(17) -0.0081(14) 0.0074(14) 0.0052(15)
C3 0.0546(18) 0.0457(16) 0.0534(17) -0.0004(14) -0.0046(15) 0.0003(15)
C4 0.0606(18) 0.0498(16) 0.0342(14) 0.0023(13) 0.0007(13) -0.0037(15)
C5 0.0471(16) 0.0438(15) 0.0292(13) -0.0008(12) 0.0023(12) -0.0082(13)
C6 0.0452(15) 0.0423(14) 0.0293(13) -0.0012(12) 0.0034(12) -0.0033(13)
C7 0.0540(17) 0.0531(16) 0.0254(13) -0.0010(12) 0.0028(12) -0.0067(14)
C8 0.0422(15) 0.0477(15) 0.0297(13) -0.0026(12) 0.0068(11) -0.0062(13)
C9 0.0403(15) 0.0472(16) 0.0319(14) -0.0026(12) 0.0027(12) -0.0061(13)
C10 0.0615(18) 0.0615(18) 0.0379(15) 0.0037(14) -0.0017(13) 0.0054(16)
C11 0.122(3) 0.062(2) 0.079(2) 0.0222(18) -0.006(2) -0.012(2)
C12 0.0469(16) 0.0580(17) 0.0388(15) -0.0036(13) 0.0095(13) -0.0042(15)
C13 0.070(2) 0.075(2) 0.0450(16) -0.0192(15) 0.0053(15) 0.0069(18)
C14 0.094(3) 0.065(2) 0.066(2) -0.0146(17) 0.0009(18) 0.005(2)
C15 0.074(2) 0.071(2) 0.076(2) 0.0048(18) -0.0099(18) 0.0147(19)
N1 0.0526(14) 0.0480(13) 0.0226(11) -0.0011(10) 0.0040(10) -0.0011(12)
O1 0.0937(16) 0.0732(14) 0.0240(10) 0.0021(9) 0.0103(9) 0.0088(12)
O2 0.0464(12) 0.0922(17) 0.0833(15) -0.0249(13) 0.0048(11) 0.0029(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.371(4) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.401(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 C15 1.505(4) . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 C7 1.461(4) . ?
C6 N1 1.383(3) . ?
C7 O1 1.257(3) . ?
C7 C8 1.434(3) . ?
C8 C9 1.388(3) . ?
C8 C12 1.488(4) . ?
C9 N1 1.342(3) . ?
C9 C10 1.504(3) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.218(3) . ?
C12 C13 1.509(4) . ?
C13 C14 1.505(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1A 0.94(3) . ?

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
C2 C1 C6 119.8(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 C15 122.0(3) . . ?
C2 C3 C15 120.2(3) . . ?
C3 C4 C5 122.5(2) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 C7 119.8(2) . . ?
C4 C5 C7 122.1(2) . . ?
N1 C6 C1 120.5(2) . . ?
N1 C6 C5 119.3(2) . . ?
C1 C6 C5 120.2(2) . . ?
O1 C7 C8 122.6(2) . . ?
O1 C7 C5 120.5(2) . . ?
C8 C7 C5 116.9(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 C12 119.6(2) . . ?
C7 C8 C12 120.0(2) . . ?
N1 C9 C8 120.7(2) . . ?
N1 C9 C10 114.3(2) . . ?
C8 C9 C10 124.9(2) . . ?
C9 C10 C11 112.0(2) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C8 122.0(2) . . ?
O2 C12 C13 120.0(3) . . ?
C8 C12 C13 117.9(2) . . ?
C14 C13 C12 113.4(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C6 123.0(2) . . ?
C9 N1 H1A 118.0(16) . . ?
C6 N1 H1A 119.0(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 C15 178.2(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C15 C3 C4 C5 -178.4(3) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C7 -178.8(2) . . . . ?
C2 C1 C6 N1 -179.9(2) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C4 C5 C6 N1 179.7(2) . . . . ?
C7 C5 C6 N1 -1.7(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C7 C5 C6 C1 178.2(2) . . . . ?
C6 C5 C7 O1 178.5(2) . . . . ?
C4 C5 C7 O1 -2.9(4) . . . . ?
C6 C5 C7 C8 -0.4(3) . . . . ?
C4 C5 C7 C8 178.2(2) . . . . ?
O1 C7 C8 C9 -176.7(2) . . . . ?
C5 C7 C8 C9 2.2(3) . . . . ?
O1 C7 C8 C12 7.7(4) . . . . ?
C5 C7 C8 C12 -173.3(2) . . . . ?
C7 C8 C9 N1 -1.9(4) . . . . ?
C12 C8 C9 N1 173.6(2) . . . . ?
C7 C8 C9 C10 -177.4(2) . . . . ?
C12 C8 C9 C10 -1.9(4) . . . . ?
N1 C9 C10 C11 -99.6(3) . . . . ?
C8 C9 C10 C11 76.1(4) . . . . ?
C9 C8 C12 O2 46.2(4) . . . . ?
C7 C8 C12 O2 -138.2(3) . . . . ?
C9 C8 C12 C13 -130.2(3) . . . . ?
C7 C8 C12 C13 45.3(3) . . . . ?
O2 C12 C13 C14 -20.0(4) . . . . ?
C8 C12 C13 C14 156.5(3) . . . . ?
C8 C9 N1 C6 -0.3(4) . . . . ?
C10 C9 N1 C6 175.7(2) . . . . ?
C1 C6 N1 C9 -177.8(2) . . . . ?
C5 C6 N1 C9 2.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039