# Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2009
data_global
_journal_name_full               'Green Chemistry'

_journal_coden_Cambridge         1048

_publ_contact_author_name        'Nirup Mondal'
_publ_contact_author_email       NIRUP@IICB.RES.IN

_publ_section_title              
;
Basic alumina-supported highly effective
Suzuki-Miyaura cross coupling reaction under microwave
irradiation:Application to fused tricyclic-oxa-aza-quinolones
;
loop_
_publ_author_name
'Nirup Mondal'
'Sukdeb Banerjee'
'Abhijit Hazra'
'Subhendu Naskar'
'Priyankar Paira'
'Rupankar Paira'
'Pritam Saha'
;
K.B.Sahu
;
# Attachment 'final.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 711585'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            oxazinoquinoline
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N O2 S2'
_chemical_formula_weight         351.42

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.655(2)
_cell_length_b                   9.619(3)
_cell_length_c                   10.727(3)
_cell_angle_alpha                83.143(5)
_cell_angle_beta                 72.938(4)
_cell_angle_gamma                64.907(4)
_cell_volume                     773.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7752
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      28.46

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Yellowish
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_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_standards_number         n/a
_diffrn_measurement_device       'Kappa Apex 2 CCD system'
_diffrn_measurement_method       ?
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            7752
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         28.46
_reflns_number_total             3454
_reflns_number_gt                2479
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa Apex 2'
_computing_cell_refinement       'Kappa Apex 2'
_computing_data_reduction        'Kappa Apex 2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)

_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     
;
_refine_ls_weighting_details
w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.1787P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     214
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_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 1.1110(3) 0.1830(2) 0.4480(2) 0.0480(5) Uani 1 1 d . . .
C2 C 1.1348(3) 0.2742(3) 0.3343(2) 0.0513(5) Uani 1 1 d . . .
H2 H 1.2401 0.2358 0.2685 0.062 Uiso 1 1 calc R . .
C3 C 1.00981(15) 0.41378(14) 0.31923(12) 0.0487(5) Uani 1 1 d . . .
H3 H 1.0300 0.4680 0.2429 0.058 Uiso 1 1 calc R . .
C4 C 0.71188(15) 0.62669(14) 0.40751(12) 0.0393(4) Uani 1 1 d . . .
C5 C 0.57140(15) 0.68822(14) 0.51647(12) 0.0393(4) Uani 1 1 d . . .
H5 H 0.4863 0.7870 0.5118 0.047 Uiso 1 1 calc R . .
C6 C 0.5524(2) 0.6075(2) 0.63343(18) 0.0369(4) Uani 1 1 d . . .
C7 C 0.6778(2) 0.4599(2) 0.63962(19) 0.0389(4) Uani 1 1 d . . .
C8 C 0.8256(2) 0.3967(2) 0.53305(19) 0.0387(4) Uani 1 1 d . . .
C9 C 0.8464(2) 0.4802(2) 0.41855(19) 0.0402(5) Uani 1 1 d . . .
O2 O 0.65639(19) 0.37646(15) 0.75177(14) 0.0470(4) Uani 1 1 d . . .
O1 O 1.2190(2) 0.05343(18) 0.46522(18) 0.0623(5) Uani 1 1 d . . .
N1 N 0.9544(2) 0.25005(19) 0.54358(17) 0.0431(4) Uani 1 1 d . . .
C18 C 0.7318(3) 0.2156(2) 0.7256(2) 0.0476(5) Uani 1 1 d . . .
H18A H 0.6748 0.1950 0.6689 0.057 Uiso 1 1 calc R . .
H18B H 0.7125 0.1606 0.8065 0.057 Uiso 1 1 calc R . .
C19 C 0.9250(3) 0.1620(2) 0.6622(2) 0.0490(5) Uani 1 1 d . . .
H19A H 0.9833 0.1749 0.7217 0.059 Uiso 1 1 calc R . .
H19B H 0.9751 0.0537 0.6406 0.059 Uiso 1 1 calc R . .
C11 C 0.7103(3) 0.7141(2) 0.28457(19) 0.0427(5) Uani 1 1 d . . .
C12 C 0.7425(3) 0.6512(3) 0.1644(2) 0.0564(6) Uani 1 1 d . . .
H12 H 0.7811 0.5470 0.1492 0.068 Uiso 1 1 calc R A 1
S13A S 0.7027(3) 0.7871(2) 0.0507(2) 0.0691(3) Uani 0.457(2) 1 d PD B 1
C14A C 0.6425(14) 0.9382(14) 0.1597(8) 0.0691(3) Uani 0.457(2) 1 d PD B 1
H14A H 0.6070 1.0422 0.1406 0.083 Uiso 0.457(2) 1 calc PR B 1
C13B C 0.7204(11) 0.7437(8) 0.0615(9) 0.0691(3) Uani 0.543(2) 1 d PD B 2
H13B H 0.7364 0.7162 -0.0231 0.083 Uiso 0.543(2) 1 calc PR B 2
S14B S 0.6516(3) 0.9362(3) 0.12392(13) 0.0691(3) Uani 0.543(2) 1 d PD B 2
C15 C 0.6588(3) 0.8712(3) 0.2761(2) 0.0538(6) Uani 1 1 d D . .
H15 H 0.6361 0.9290 0.3481 0.065 Uiso 1 1 calc R B 1
C41 C 0.3975(2) 0.6783(2) 0.74571(18) 0.0378(4) Uani 1 1 d . . .
C42 C 0.2327(3) 0.7842(2) 0.7305(2) 0.0467(5) Uani 1 1 d D . .
H42 H 0.2142 0.8178 0.6490 0.060(7) Uiso 1 1 calc R C 1
C43A C 0.1004(7) 0.8349(6) 0.8439(4) 0.0574(3) Uani 0.7530(19) 1 d PD D 1
H43A H -0.0160 0.9040 0.8499 0.069 Uiso 0.7530(19) 1 calc PR D 1
S44A S 0.18718(12) 0.74770(12) 0.97641(9) 0.0574(3) Uani 0.7530(19) 1 d PD D 1
S43B S 0.0869(5) 0.8394(5) 0.8701(3) 0.0574(3) Uani 0.2470(19) 1 d PD D 2
C44B C 0.2482(15) 0.7292(16) 0.9563(12) 0.0574(3) Uani 0.2470(19) 1 d PD D 2
H44B H 0.2297 0.7296 1.0461 0.069 Uiso 0.2470(19) 1 calc PR D 2
C45 C 0.3913(3) 0.6508(3) 0.8750(2) 0.0507(5) Uani 1 1 d D . .
H45 H 0.4889 0.5857 0.9043 0.061 Uiso 1 1 calc R D 1

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 0.0353(10) 0.0465(13) 0.0587(14) -0.0169(10) -0.0147(9) -0.0079(9)
C2 0.0348(10) 0.0600(14) 0.0512(13) -0.0168(11) -0.0059(9) -0.0115(10)
C3 0.0391(11) 0.0554(14) 0.0490(12) -0.0092(10) -0.0059(9) -0.0184(10)
C4 0.0384(10) 0.0409(11) 0.0403(11) -0.0007(8) -0.0113(8) -0.0171(8)
C5 0.0370(10) 0.0355(10) 0.0424(11) -0.0016(8) -0.0120(8) -0.0108(8)
C6 0.0332(9) 0.0351(10) 0.0401(10) -0.0017(8) -0.0109(8) -0.0107(8)
C7 0.0360(10) 0.0386(11) 0.0414(11) -0.0008(8) -0.0118(8) -0.0136(8)
C8 0.0329(9) 0.0342(10) 0.0472(11) -0.0043(8) -0.0156(8) -0.0079(8)
C9 0.0335(10) 0.0448(12) 0.0421(11) -0.0081(9) -0.0078(8) -0.0154(9)
O2 0.0473(8) 0.0354(8) 0.0465(8) 0.0040(6) -0.0104(6) -0.0083(6)
O1 0.0459(9) 0.0479(10) 0.0759(11) -0.0162(8) -0.0189(8) 0.0027(7)
N1 0.0345(9) 0.0392(9) 0.0509(10) -0.0059(8) -0.0136(7) -0.0077(7)
C18 0.0464(12) 0.0355(11) 0.0561(13) 0.0022(9) -0.0162(10) -0.0113(9)
C19 0.0445(11) 0.0395(12) 0.0572(13) -0.0002(10) -0.0200(10) -0.0074(9)
C11 0.0358(10) 0.0502(12) 0.0423(11) 0.0000(9) -0.0063(8) -0.0206(9)
C12 0.0589(14) 0.0672(16) 0.0461(13) 0.0007(11) -0.0108(10) -0.0308(12)
S13A 0.0755(6) 0.0797(7) 0.0524(7) 0.0188(7) -0.0145(5) -0.0386(6)
C14A 0.0755(6) 0.0797(7) 0.0524(7) 0.0188(7) -0.0145(5) -0.0386(6)
C13B 0.0755(6) 0.0797(7) 0.0524(7) 0.0188(7) -0.0145(5) -0.0386(6)
S14B 0.0755(6) 0.0797(7) 0.0524(7) 0.0188(7) -0.0145(5) -0.0386(6)
C15 0.0558(14) 0.0569(14) 0.0507(13) 0.0051(11) -0.0131(10) -0.0271(11)
C41 0.0382(10) 0.0332(10) 0.0383(10) -0.0019(8) -0.0089(8) -0.0116(8)
C42 0.0436(11) 0.0456(12) 0.0417(12) -0.0026(9) -0.0103(9) -0.0098(9)
C43A 0.0574(5) 0.0578(5) 0.0400(5) -0.0050(3) 0.0005(4) -0.0152(4)
S44A 0.0574(5) 0.0578(5) 0.0400(5) -0.0050(3) 0.0005(4) -0.0152(4)
S43B 0.0574(5) 0.0578(5) 0.0400(5) -0.0050(3) 0.0005(4) -0.0152(4)
C44B 0.0574(5) 0.0578(5) 0.0400(5) -0.0050(3) 0.0005(4) -0.0152(4)
C45 0.0542(13) 0.0452(12) 0.0436(12) 0.0009(9) -0.0149(10) -0.0110(10)

_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 O1 1.233(2) . ?
C1 N1 1.380(3) . ?
C1 C2 1.432(3) . ?
C2 C3 1.348(3) . ?
C3 C9 1.433(2) . ?
C4 C5 1.384(2) . ?
C4 C9 1.416(2) . ?
C4 C11 1.477(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.382(3) . ?
C6 C41 1.478(3) . ?
C7 O2 1.375(2) . ?
C7 C8 1.401(3) . ?
C8 C9 1.394(3) . ?
C8 N1 1.395(2) . ?
O2 C18 1.428(2) . ?
N1 C19 1.462(3) . ?
C18 C19 1.486(3) . ?
C11 C15 1.383(3) . ?
C11 C12 1.392(3) . ?
C12 C13B 1.338(8) . ?
C12 S13A 1.673(3) . ?
S13A C14A 1.777(10) . ?
C14A C15 1.351(9) . ?
C13B S14B 1.833(8) . ?
S14B C15 1.686(3) . ?
C41 C45 1.370(3) . ?
C41 C42 1.401(3) . ?
C42 C43A 1.371(5) . ?
C42 S43B 1.622(4) . ?
C43A S44A 1.759(5) . ?
S44A C45 1.700(2) . ?
S43B C44B 1.787(13) . ?
C44B C45 1.263(11) . ?

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
O1 C1 N1 119.6(2) . . ?
O1 C1 C2 124.9(2) . . ?
N1 C1 C2 115.50(18) . . ?
C3 C2 C1 122.34(18) . . ?
C2 C3 C9 121.29(15) . . ?
C5 C4 C9 118.12(9) . . ?
C5 C4 C11 118.46(9) . . ?
C9 C4 C11 123.38(14) . . ?
C4 C5 C6 122.57(9) . . ?
C7 C6 C5 118.60(16) . . ?
C7 C6 C41 121.32(17) . . ?
C5 C6 C41 120.06(15) . . ?
O2 C7 C6 119.30(17) . . ?
O2 C7 C8 120.42(17) . . ?
C6 C7 C8 120.28(18) . . ?
C9 C8 N1 120.14(18) . . ?
C9 C8 C7 120.58(18) . . ?
N1 C8 C7 119.27(18) . . ?
C8 C9 C4 119.56(16) . . ?
C8 C9 C3 117.05(17) . . ?
C4 C9 C3 123.34(16) . . ?
C7 O2 C18 111.95(15) . . ?
C1 N1 C8 123.50(18) . . ?
C1 N1 C19 117.51(17) . . ?
C8 N1 C19 118.98(17) . . ?
O2 C18 C19 109.72(18) . . ?
N1 C19 C18 109.75(17) . . ?
C15 C11 C12 111.1(2) . . ?
C15 C11 C4 124.44(19) . . ?
C12 C11 C4 124.13(19) . . ?
C13B C12 C11 119.2(4) . . ?
C13B C12 S13A 8.0(4) . . ?
C11 C12 S13A 111.3(2) . . ?
C12 S13A C14A 93.7(4) . . ?
C15 C14A S13A 106.0(7) . . ?
C12 C13B S14B 104.9(6) . . ?
C15 S14B C13B 92.6(3) . . ?
C14A C15 C11 117.9(5) . . ?
C14A C15 S14B 6.0(5) . . ?
C11 C15 S14B 112.1(2) . . ?
C45 C41 C42 110.97(18) . . ?
C45 C41 C6 126.58(18) . . ?
C42 C41 C6 122.44(18) . . ?
C43A C42 C41 115.4(3) . . ?
C43A C42 S43B 4.0(4) . . ?
C41 C42 S43B 111.5(2) . . ?
C42 C43A S44A 108.7(4) . . ?
C45 S44A C43A 91.63(18) . . ?
C42 S43B C44B 91.6(5) . . ?
C45 C44B S43B 108.8(9) . . ?
C44B C45 C41 116.7(6) . . ?
C44B C45 S44A 6.6(7) . . ?
C41 C45 S44A 113.20(17) . . ?

_diffrn_measured_fraction_theta_max 0.883
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.883
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.044

_publ_section_references         
;

Sheldrick, G.M. (1997) SHELXL program for crystallography refinement.
University of Gottingen, Germany.

;

#===END