# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Yuanjiang Pan'
_publ_contact_author_email       CHEYJPAN@ZJU.EDU.CN

_publ_section_title              
;
Chemo-/Regioselective Synthesis of 6-Unsubstituted
Dihydropyrimidinones, 1,3-Thiazines and Chromones via Novel Variants
of Biginelli Reaction
;
loop_
_publ_author_name
'Yuanjiang Pan'
'Jie-Ping Wan'

# Attachment '4d.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 707892'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C136 H104 Cl8 N16 O8 S8'
_chemical_formula_weight         2630.51

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.147(4)
_cell_length_b                   8.3692(17)
_cell_length_c                   18.124(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3207.6(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28828
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.42
_reflns_number_total             7269
_reflns_number_gt                4766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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^)+(0.0679P)^2^+0.0035P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.31(6)
_refine_ls_number_reflns         7269
_refine_ls_number_parameters     401
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.001
_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 0.39965(16) 0.9143(4) 0.5795(2) 0.0537(8) Uani 1 1 d . . .
H1A H 0.4303 0.8513 0.5569 0.064 Uiso 1 1 calc R . .
C2 C 0.4174(2) 1.0205(4) 0.6345(2) 0.0674(11) Uani 1 1 d . . .
H2A H 0.4596 1.0287 0.6487 0.081 Uiso 1 1 calc R . .
C3 C 0.3720(2) 1.1134(4) 0.6676(2) 0.0686(11) Uani 1 1 d . . .
C4 C 0.3107(2) 1.1054(5) 0.6465(2) 0.0744(12) Uani 1 1 d . . .
H4A H 0.2807 1.1716 0.6683 0.089 Uiso 1 1 calc R . .
C5 C 0.29256(18) 0.9969(4) 0.5916(2) 0.0597(9) Uani 1 1 d . . .
H5A H 0.2503 0.9897 0.5778 0.072 Uiso 1 1 calc R . .
C6 C 0.33720(14) 0.9000(3) 0.55750(17) 0.0430(7) Uani 1 1 d . . .
C7 C 0.31849(14) 0.7775(3) 0.49920(17) 0.0396(6) Uani 1 1 d . . .
H7A H 0.3569 0.7433 0.4734 0.047 Uiso 1 1 calc R . .
C8 C 0.23106(14) 0.5798(4) 0.52472(18) 0.0435(7) Uani 1 1 d . . .
C9 C 0.21491(13) 0.7863(4) 0.43520(19) 0.0467(7) Uani 1 1 d . . .
H9A H 0.1881 0.8304 0.4000 0.056 Uiso 1 1 calc R . .
C10 C 0.27337(12) 0.8468(3) 0.44293(17) 0.0404(6) Uani 1 1 d . . .
C11 C 0.29768(13) 0.9694(3) 0.39412(17) 0.0414(7) Uani 1 1 d . . .
C12 C 0.25186(14) 1.0710(3) 0.35089(17) 0.0424(7) Uani 1 1 d . . .
C13 C 0.20493(17) 1.1522(4) 0.3873(2) 0.0615(9) Uani 1 1 d . . .
H13A H 0.1988 1.1375 0.4376 0.074 Uiso 1 1 calc R . .
C14 C 0.1665(2) 1.2571(5) 0.3476(3) 0.0799(13) Uani 1 1 d . . .
H14A H 0.1359 1.3170 0.3720 0.096 Uiso 1 1 calc R . .
C15 C 0.1736(2) 1.2719(5) 0.2734(3) 0.0860(14) Uani 1 1 d . . .
H15A H 0.1468 1.3385 0.2467 0.103 Uiso 1 1 calc R . .
C16 C 0.2197(2) 1.1895(6) 0.2383(3) 0.0862(14) Uani 1 1 d . . .
H16A H 0.2243 1.1999 0.1875 0.103 Uiso 1 1 calc R . .
C17 C 0.25994(19) 1.0905(4) 0.2765(2) 0.0659(10) Uani 1 1 d . . .
H17A H 0.2923 1.0373 0.2520 0.079 Uiso 1 1 calc R . .
C18 C 0.35667(15) 0.4030(4) 0.4001(2) 0.0521(8) Uani 1 1 d . . .
H18A H 0.3276 0.3323 0.4206 0.062 Uiso 1 1 calc R . .
C19 C 0.33872(18) 0.4965(4) 0.3408(2) 0.0599(9) Uani 1 1 d . . .
H19A H 0.2982 0.4881 0.3212 0.072 Uiso 1 1 calc R . .
C20 C 0.38155(18) 0.6017(4) 0.3115(2) 0.0569(9) Uani 1 1 d . . .
C21 C 0.4411(2) 0.6203(4) 0.3407(2) 0.0617(9) Uani 1 1 d . . .
H21A H 0.4691 0.6953 0.3215 0.074 Uiso 1 1 calc R . .
C22 C 0.45849(15) 0.5229(4) 0.40019(19) 0.0525(8) Uani 1 1 d . . .
H22A H 0.4988 0.5331 0.4203 0.063 Uiso 1 1 calc R . .
C23 C 0.41729(12) 0.4124(3) 0.42966(17) 0.0391(6) Uani 1 1 d . . .
C24 C 0.43637(13) 0.2982(3) 0.49132(17) 0.0404(6) Uani 1 1 d . . .
H24A H 0.3979 0.2664 0.5176 0.048 Uiso 1 1 calc R . .
C25 C 0.52105(13) 0.0917(3) 0.46927(18) 0.0432(7) Uani 1 1 d . . .
C26 C 0.53891(14) 0.3019(4) 0.55684(18) 0.0470(7) Uani 1 1 d . . .
H26A H 0.5660 0.3470 0.5915 0.056 Uiso 1 1 calc R . .
C27 C 0.48139(13) 0.3677(4) 0.54694(17) 0.0411(7) Uani 1 1 d . . .
C28 C 0.45722(14) 0.4939(3) 0.59463(16) 0.0422(7) Uani 1 1 d . . .
C29 C 0.49901(15) 0.5958(3) 0.64111(18) 0.0446(7) Uani 1 1 d . . .
C30 C 0.55607(17) 0.6563(4) 0.6158(2) 0.0635(9) Uani 1 1 d . . .
H30A H 0.5714 0.6266 0.5697 0.076 Uiso 1 1 calc R . .
C31 C 0.5903(2) 0.7621(5) 0.6598(3) 0.0873(15) Uani 1 1 d . . .
H31A H 0.6286 0.8028 0.6430 0.105 Uiso 1 1 calc R . .
C32 C 0.5677(2) 0.8061(5) 0.7276(3) 0.0770(11) Uani 1 1 d . . .
H32A H 0.5906 0.8773 0.7567 0.092 Uiso 1 1 calc R . .
C33 C 0.5120(2) 0.7463(4) 0.7527(2) 0.0673(11) Uani 1 1 d . . .
H33A H 0.4972 0.7757 0.7991 0.081 Uiso 1 1 calc R . .
C34 C 0.47708(18) 0.6418(4) 0.7098(2) 0.0557(8) Uani 1 1 d . . .
Cl1 Cl 0.39402(9) 1.24235(15) 0.73873(8) 0.1199(6) Uani 1 1 d . . .
Cl2 Cl 0.36044(6) 0.71882(13) 0.23557(6) 0.0856(3) Uani 1 1 d . . .
H34A H 0.4349(17) 0.610(4) 0.728(2) 0.058(9) Uiso 1 1 d . . .
N1 N 0.28925(11) 0.6356(3) 0.53334(15) 0.0452(6) Uani 1 1 d . . .
H1B H 0.3098 0.5883 0.5574 0.054 Uiso 1 1 d R . .
N2 N 0.19333(11) 0.6620(3) 0.47731(17) 0.0579(8) Uani 1 1 d . . .
H2B H 0.1601 0.6325 0.4743 0.070 Uiso 1 1 d R . .
N3 N 0.55908(11) 0.1722(3) 0.51819(16) 0.0549(7) Uani 1 1 d . . .
H3B H 0.5988 0.1246 0.5278 0.066 Uiso 1 1 d R . .
N4 N 0.46438(11) 0.1523(3) 0.45792(14) 0.0419(6) Uani 1 1 d . . .
H4B H 0.4331 0.1018 0.4298 0.050 Uiso 1 1 d R . .
O1 O 0.35491(9) 0.9932(3) 0.38865(14) 0.0531(6) Uani 1 1 d . . .
O2 O 0.39947(10) 0.5168(3) 0.59676(13) 0.0557(6) Uani 1 1 d . . .
S1 S 0.20497(4) 0.41793(10) 0.56990(5) 0.0564(2) Uani 1 1 d . . .
S2 S 0.54638(4) -0.07478(10) 0.42683(6) 0.0600(3) 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 0.0485(18) 0.0547(17) 0.058(2) 0.0189(16) -0.0099(16) -0.0091(15)
C2 0.073(2) 0.064(2) 0.065(2) 0.026(2) -0.029(2) -0.028(2)
C3 0.104(3) 0.0472(18) 0.055(2) 0.0144(17) -0.021(2) -0.011(2)
C4 0.115(4) 0.057(2) 0.051(2) 0.0006(18) -0.009(2) 0.018(2)
C5 0.062(2) 0.067(2) 0.051(2) 0.0027(17) -0.0120(17) 0.0118(18)
C6 0.0462(17) 0.0423(14) 0.0406(17) 0.0127(13) -0.0076(14) 0.0010(13)
C7 0.0299(14) 0.0486(15) 0.0403(15) 0.0093(13) -0.0045(12) 0.0014(13)
C8 0.0346(15) 0.0499(16) 0.0462(17) 0.0041(14) -0.0055(14) -0.0007(13)
C9 0.0367(15) 0.0514(16) 0.0521(18) 0.0156(15) -0.0085(15) -0.0016(13)
C10 0.0342(14) 0.0444(15) 0.0426(16) 0.0085(13) -0.0031(13) -0.0031(12)
C11 0.0405(16) 0.0447(15) 0.0391(16) 0.0026(13) -0.0060(13) -0.0004(13)
C12 0.0425(16) 0.0430(15) 0.0419(16) 0.0109(13) -0.0036(14) -0.0029(13)
C13 0.062(2) 0.062(2) 0.061(2) 0.0122(18) 0.0035(18) 0.0161(18)
C14 0.063(3) 0.070(2) 0.106(4) 0.028(3) 0.013(3) 0.019(2)
C15 0.071(3) 0.075(3) 0.112(4) 0.042(3) -0.027(3) 0.004(2)
C16 0.101(3) 0.098(3) 0.060(2) 0.036(3) -0.029(3) -0.002(3)
C17 0.078(3) 0.072(2) 0.048(2) 0.0093(19) -0.0054(19) 0.0037(19)
C18 0.0478(18) 0.0487(17) 0.060(2) 0.0036(15) -0.0154(16) -0.0046(13)
C19 0.060(2) 0.0583(19) 0.062(2) -0.0003(18) -0.0248(18) 0.0029(17)
C20 0.075(3) 0.0481(17) 0.0479(19) -0.0041(16) -0.0123(18) 0.0133(17)
C21 0.074(3) 0.0527(19) 0.058(2) 0.0108(17) -0.0004(19) -0.0030(18)
C22 0.0466(17) 0.0589(18) 0.0521(19) 0.0070(16) -0.0071(15) -0.0055(15)
C23 0.0371(14) 0.0380(13) 0.0422(16) -0.0017(12) -0.0051(14) 0.0004(11)
C24 0.0338(15) 0.0449(15) 0.0426(16) -0.0025(14) -0.0019(13) 0.0019(13)
C25 0.0343(15) 0.0466(16) 0.0488(18) -0.0020(14) -0.0027(13) -0.0011(12)
C26 0.0382(15) 0.0495(16) 0.053(2) -0.0106(15) -0.0124(14) 0.0045(14)
C27 0.0381(15) 0.0445(15) 0.0406(16) -0.0019(12) -0.0041(13) -0.0004(13)
C28 0.0430(16) 0.0435(15) 0.0401(17) 0.0035(13) -0.0075(14) 0.0052(13)
C29 0.0512(18) 0.0387(14) 0.0440(16) -0.0001(13) -0.0105(14) 0.0076(13)
C30 0.064(2) 0.064(2) 0.063(2) -0.0109(19) 0.0049(18) -0.0135(18)
C31 0.071(3) 0.088(3) 0.103(4) -0.016(3) -0.007(3) -0.036(2)
C32 0.087(3) 0.067(2) 0.077(3) -0.015(2) -0.020(3) -0.018(2)
C33 0.088(3) 0.065(2) 0.048(3) -0.0114(17) -0.0161(19) 0.006(2)
C34 0.062(2) 0.0528(18) 0.052(2) -0.0060(16) -0.0061(17) 0.0070(17)
Cl1 0.2125(17) 0.0817(7) 0.0654(7) -0.0022(6) -0.0351(10) -0.0424(9)
Cl2 0.1231(9) 0.0788(6) 0.0550(5) 0.0145(5) -0.0165(6) 0.0261(6)
N1 0.0365(13) 0.0472(13) 0.0519(15) 0.0153(12) -0.0086(12) 0.0009(11)
N2 0.0347(14) 0.0606(17) 0.079(2) 0.0317(16) -0.0161(14) -0.0087(12)
N3 0.0344(13) 0.0604(16) 0.0700(19) -0.0215(15) -0.0164(13) 0.0110(12)
N4 0.0370(12) 0.0402(12) 0.0485(15) -0.0024(11) -0.0087(11) -0.0014(10)
O1 0.0386(11) 0.0614(14) 0.0593(14) 0.0134(12) -0.0026(10) -0.0060(10)
O2 0.0404(12) 0.0664(14) 0.0604(15) -0.0118(12) -0.0125(11) 0.0128(10)
S1 0.0482(4) 0.0514(4) 0.0697(6) 0.0224(4) -0.0103(4) -0.0085(4)
S2 0.0457(4) 0.0535(5) 0.0807(7) -0.0219(5) -0.0110(4) 0.0064(4)

_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 C6 1.385(4) . ?
C1 C2 1.388(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.355(6) . ?
C3 Cl1 1.744(4) . ?
C4 C5 1.400(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.525(4) . ?
C7 N1 1.475(4) . ?
C7 C10 1.512(4) . ?
C7 H7A 0.9800 . ?
C8 N1 1.326(4) . ?
C8 N2 1.360(4) . ?
C8 S1 1.676(3) . ?
C9 C10 1.343(4) . ?
C9 N2 1.368(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.449(4) . ?
C11 O1 1.231(3) . ?
C11 C12 1.509(4) . ?
C12 C17 1.369(5) . ?
C12 C13 1.372(5) . ?
C13 C14 1.396(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.359(7) . ?
C14 H14A 0.9300 . ?
C15 C16 1.354(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.382(5) . ?
C18 C23 1.392(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.371(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(5) . ?
C20 Cl2 1.747(4) . ?
C21 C22 1.401(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.525(4) . ?
C24 N4 1.486(4) . ?
C24 C27 1.503(4) . ?
C24 H24A 0.9800 . ?
C25 N4 1.317(4) . ?
C25 N3 1.374(4) . ?
C25 S2 1.679(3) . ?
C26 C27 1.347(4) . ?
C26 N3 1.360(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.458(4) . ?
C28 O2 1.237(3) . ?
C28 C29 1.489(4) . ?
C29 C34 1.383(5) . ?
C29 C30 1.387(5) . ?
C30 C31 1.394(5) . ?
C30 H30A 0.9300 . ?
C31 C32 1.370(7) . ?
C31 H31A 0.9300 . ?
C32 C33 1.359(6) . ?
C32 H32A 0.9300 . ?
C33 C34 1.384(5) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.99(3) . ?
N1 H1B 0.7314 . ?
N2 H2B 0.7473 . ?
N3 H3B 0.9464 . ?
N4 H4B 0.9368 . ?

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
C6 C1 C2 121.4(4) . . ?
C6 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 Cl1 119.7(4) . . ?
C2 C3 Cl1 119.2(3) . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 121.6(3) . . ?
N1 C7 C10 109.1(2) . . ?
N1 C7 C6 111.1(3) . . ?
C10 C7 C6 111.9(2) . . ?
N1 C7 H7A 108.2 . . ?
C10 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
N1 C8 N2 116.2(3) . . ?
N1 C8 S1 122.2(2) . . ?
N2 C8 S1 121.6(2) . . ?
C10 C9 N2 122.4(3) . . ?
C10 C9 H9A 118.8 . . ?
N2 C9 H9A 118.8 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 C7 120.4(3) . . ?
C11 C10 C7 117.4(2) . . ?
O1 C11 C10 120.9(3) . . ?
O1 C11 C12 119.9(3) . . ?
C10 C11 C12 119.2(2) . . ?
C17 C12 C13 120.3(3) . . ?
C17 C12 C11 119.9(3) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 119.0(4) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 121.2(5) . . ?
C15 C16 H16A 119.4 . . ?
C17 C16 H16A 119.4 . . ?
C12 C17 C16 119.4(4) . . ?
C12 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C19 C18 C23 121.3(3) . . ?
C19 C18 H18A 119.3 . . ?
C23 C18 H18A 119.3 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 Cl2 119.8(3) . . ?
C21 C20 Cl2 118.3(3) . . ?
C20 C21 C22 118.1(3) . . ?
C20 C21 H21A 121.0 . . ?
C22 C21 H21A 121.0 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22A 119.2 . . ?
C21 C22 H22A 119.2 . . ?
C22 C23 C18 118.1(3) . . ?
C22 C23 C24 122.5(3) . . ?
C18 C23 C24 119.4(3) . . ?
N4 C24 C27 109.8(2) . . ?
N4 C24 C23 108.8(2) . . ?
C27 C24 C23 114.6(2) . . ?
N4 C24 H24A 107.8 . . ?
C27 C24 H24A 107.8 . . ?
C23 C24 H24A 107.8 . . ?
N4 C25 N3 116.4(3) . . ?
N4 C25 S2 122.6(2) . . ?
N3 C25 S2 121.0(2) . . ?
C27 C26 N3 122.7(3) . . ?
C27 C26 H26A 118.6 . . ?
N3 C26 H26A 118.6 . . ?
C26 C27 C28 122.3(3) . . ?
C26 C27 C24 120.2(3) . . ?
C28 C27 C24 117.1(2) . . ?
O2 C28 C27 118.5(3) . . ?
O2 C28 C29 118.7(3) . . ?
C27 C28 C29 122.8(3) . . ?
C34 C29 C30 119.2(3) . . ?
C34 C29 C28 118.0(3) . . ?
C30 C29 C28 122.6(3) . . ?
C29 C30 C31 119.7(4) . . ?
C29 C30 H30A 120.2 . . ?
C31 C30 H30A 120.2 . . ?
C32 C31 C30 120.2(4) . . ?
C32 C31 H31A 119.9 . . ?
C30 C31 H31A 119.9 . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C32 C33 C34 120.5(4) . . ?
C32 C33 H33A 119.7 . . ?
C34 C33 H33A 119.7 . . ?
C29 C34 C33 120.2(4) . . ?
C29 C34 H34A 122(2) . . ?
C33 C34 H34A 118(2) . . ?
C8 N1 C7 128.6(2) . . ?
C8 N1 H1B 115.5 . . ?
C7 N1 H1B 115.9 . . ?
C8 N2 C9 122.8(2) . . ?
C8 N2 H2B 115.5 . . ?
C9 N2 H2B 121.6 . . ?
C26 N3 C25 122.7(2) . . ?
C26 N3 H3B 121.3 . . ?
C25 N3 H3B 115.6 . . ?
C25 N4 C24 128.0(2) . . ?
C25 N4 H4B 123.6 . . ?
C24 N4 H4B 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.061