# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
K.Brahma
A.Sasmal
C.Chowdhury
_publ_contact_author_name        'Chinmay Chowdhury'
_publ_contact_author_email       chinmay@iicb.res.in

data_kb_2_140p_0m
_database_code_depnum_ccdc_archive 'CCDC 838046'
#TrackingRef 'Product-3j-0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            pyrazolobenzoxazine
_chemical_melting_point          192
_chemical_formula_moiety         'C20 H17 N3 O5'
_chemical_formula_sum            'C20 H17 N3 O5'
_chemical_formula_weight         379.37

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           Triclinic
_symmetry_space_group_name_H-M   'P-1 '

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

_cell_length_a                   9.3525(4)
_cell_length_b                   10.0265(5)
_cell_length_c                   10.8420(5)
_cell_angle_alpha                113.426(2)
_cell_angle_beta                 96.914(2)
_cell_angle_gamma                97.590(2)
_cell_volume                     907.85(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8659
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_T_max  0.9949
_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  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13611
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3186
_reflns_number_gt                2710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART 3'
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'MURCURY 2.3'

_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^)+(0.1000P)^2^+0.9360P] 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         3186
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   0.674
_refine_ls_restrained_S_all      0.674
_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
C10 C 0.93789(19) 0.29022(19) 0.30312(18) 0.0438(4) Uani 1 1 d . . .
C18 C 0.78203(19) 0.21348(19) 0.25314(17) 0.0430(4) Uani 1 1 d . . .
C15 C 0.7402(2) 0.0591(2) 0.20249(18) 0.0486(4) Uani 1 1 d . . .
C8 C 1.01916(19) 0.3625(2) 0.24325(18) 0.0465(4) Uani 1 1 d . . .
C16 C 0.5918(2) -0.0030(2) 0.16466(19) 0.0546(5) Uani 1 1 d . . .
H16 H 0.5611 -0.1051 0.1322 0.066 Uiso 1 1 calc R . .
C19 C 0.6761(2) 0.2989(2) 0.2566(2) 0.0536(5) Uani 1 1 d . . .
H19 H 0.7051 0.4008 0.2860 0.064 Uiso 1 1 calc R . .
C9 C 1.03567(19) 0.3142(2) 0.42403(18) 0.0454(4) Uani 1 1 d . . .
C17 C 0.4897(2) 0.0855(2) 0.17495(18) 0.0527(5) Uani 1 1 d . . .
C6 C 1.2699(2) 0.4959(2) 0.2909(2) 0.0486(4) Uani 1 1 d . . .
C11 C 1.0120(2) 0.2686(2) 0.5355(2) 0.0525(5) Uani 1 1 d . . .
C20 C 0.5290(2) 0.2358(2) 0.2172(2) 0.0595(5) Uani 1 1 d . . .
H20 H 0.4583 0.2933 0.2191 0.071 Uiso 1 1 calc R . .
C1 C 1.4008(2) 0.5703(2) 0.3818(2) 0.0577(5) Uani 1 1 d . . .
H1 H 1.4124 0.5789 0.4713 0.069 Uiso 1 1 calc R . .
N3 N 0.3330(2) 0.0171(3) 0.13823(19) 0.0727(6) Uani 1 1 d . . .
C5 C 1.2486(2) 0.4846(2) 0.1581(2) 0.0566(5) Uani 1 1 d . . .
C7 C 0.9913(2) 0.3924(3) 0.1192(2) 0.0599(5) Uani 1 1 d . . .
H7A H 0.9164 0.3128 0.0500 0.072 Uiso 1 1 calc R . .
H7B H 0.9548 0.4839 0.1428 0.072 Uiso 1 1 calc R . .
C14 C 0.8514(3) -0.0386(2) 0.1874(3) 0.0746(7) Uani 1 1 d . . .
H14A H 0.8823 -0.0426 0.2734 0.112 Uiso 1 1 calc R . .
H14B H 0.9347 0.0009 0.1599 0.112 Uiso 1 1 calc R . .
H14C H 0.8082 -0.1367 0.1193 0.112 Uiso 1 1 calc R . .
C2 C 1.5139(2) 0.6313(2) 0.3383(3) 0.0685(6) Uani 1 1 d . . .
H2 H 1.6036 0.6794 0.3975 0.082 Uiso 1 1 calc R . .
C3 C 1.4936(3) 0.6208(3) 0.2066(3) 0.0780(7) Uani 1 1 d . . .
H3 H 1.5700 0.6629 0.1778 0.094 Uiso 1 1 calc R . .
C4 C 1.3621(3) 0.5489(3) 0.1164(3) 0.0737(7) Uani 1 1 d . . .
H4 H 1.3499 0.5438 0.0281 0.088 Uiso 1 1 calc R . .
C12 C 0.8373(3) 0.1366(3) 0.6084(3) 0.0754(7) Uani 1 1 d . . .
H12A H 0.9141 0.0892 0.6307 0.090 Uiso 1 1 calc R . .
H12B H 0.8253 0.2153 0.6924 0.090 Uiso 1 1 calc R . .
C13 C 0.7018(4) 0.0301(4) 0.5453(3) 0.1190(13) Uani 1 1 d . . .
H13A H 0.6302 0.0742 0.5120 0.179 Uiso 1 1 calc R . .
H13B H 0.6665 -0.0004 0.6115 0.179 Uiso 1 1 calc R . .
H13C H 0.7183 -0.0546 0.4704 0.179 Uiso 1 1 calc R . .
O3 O 0.87656(15) 0.19677(17) 0.51339(15) 0.0643(4) Uani 1 1 d . . .
O1 O 1.12197(17) 0.40441(19) 0.06444(15) 0.0684(4) Uani 1 1 d . . .
O2 O 1.10296(18) 0.2949(2) 0.63343(18) 0.0882(6) Uani 1 1 d . . .
O4 O 0.2998(2) -0.1170(2) 0.0996(2) 0.0979(7) Uani 1 1 d . . .
O5 O 0.2431(2) 0.0963(3) 0.1479(2) 0.1097(8) Uani 1 1 d . . .
N1 N 1.15329(16) 0.42165(17) 0.32542(15) 0.0471(4) Uani 1 1 d . . .
N2 N 1.16705(16) 0.39328(17) 0.43645(16) 0.0489(4) 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
C10 0.0389(9) 0.0438(9) 0.0477(9) 0.0196(8) 0.0032(7) 0.0081(7)
C18 0.0393(9) 0.0471(9) 0.0411(9) 0.0193(7) 0.0022(7) 0.0058(7)
C15 0.0480(10) 0.0478(10) 0.0474(10) 0.0211(8) -0.0009(8) 0.0067(8)
C8 0.0406(9) 0.0480(10) 0.0483(10) 0.0204(8) 0.0017(7) 0.0060(7)
C16 0.0583(12) 0.0488(10) 0.0497(10) 0.0224(9) -0.0044(9) -0.0047(9)
C19 0.0445(10) 0.0465(10) 0.0597(11) 0.0149(9) -0.0002(8) 0.0086(8)
C9 0.0388(9) 0.0483(10) 0.0492(10) 0.0224(8) 0.0036(7) 0.0073(7)
C17 0.0392(10) 0.0681(12) 0.0419(9) 0.0199(9) -0.0001(7) -0.0016(9)
C6 0.0424(10) 0.0435(9) 0.0632(11) 0.0245(8) 0.0133(8) 0.0091(8)
C11 0.0456(10) 0.0587(11) 0.0532(11) 0.0276(9) 0.0000(8) 0.0058(8)
C20 0.0436(11) 0.0618(12) 0.0605(12) 0.0133(10) 0.0023(9) 0.0156(9)
C1 0.0452(11) 0.0479(10) 0.0740(13) 0.0220(10) 0.0080(9) 0.0041(8)
N3 0.0491(11) 0.0986(16) 0.0557(11) 0.0282(11) -0.0002(8) -0.0108(11)
C5 0.0524(11) 0.0557(11) 0.0682(13) 0.0308(10) 0.0161(10) 0.0124(9)
C7 0.0520(11) 0.0729(13) 0.0582(12) 0.0360(10) 0.0019(9) 0.0032(10)
C14 0.0705(15) 0.0548(12) 0.0880(16) 0.0233(12) -0.0063(12) 0.0195(11)
C2 0.0507(12) 0.0510(12) 0.1004(18) 0.0300(12) 0.0153(11) 0.0034(9)
C3 0.0602(14) 0.0655(14) 0.123(2) 0.0506(15) 0.0366(15) 0.0088(11)
C4 0.0742(16) 0.0786(15) 0.0891(17) 0.0504(14) 0.0335(13) 0.0187(13)
C12 0.0748(15) 0.0912(17) 0.0725(14) 0.0542(13) 0.0077(12) -0.0017(13)
C13 0.140(3) 0.110(2) 0.093(2) 0.0496(19) 0.020(2) -0.041(2)
O3 0.0514(8) 0.0841(10) 0.0653(9) 0.0483(8) -0.0006(7) -0.0046(7)
O1 0.0643(9) 0.0875(11) 0.0585(9) 0.0379(8) 0.0134(7) 0.0073(8)
O2 0.0629(10) 0.1322(16) 0.0746(11) 0.0661(11) -0.0154(8) -0.0122(10)
O4 0.0707(12) 0.1050(15) 0.0962(14) 0.0432(12) -0.0121(10) -0.0334(11)
O5 0.0406(9) 0.1410(19) 0.1276(18) 0.0403(15) 0.0077(10) 0.0117(11)
N1 0.0386(8) 0.0503(9) 0.0512(8) 0.0233(7) 0.0036(6) 0.0037(6)
N2 0.0412(8) 0.0539(9) 0.0505(9) 0.0243(7) 0.0012(6) 0.0050(7)

_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
C10 C8 1.368(3) . ?
C10 C9 1.420(2) . ?
C10 C18 1.481(2) . ?
C18 C19 1.387(2) . ?
C18 C15 1.401(3) . ?
C15 C16 1.383(3) . ?
C15 C14 1.501(3) . ?
C8 N1 1.354(2) . ?
C8 C7 1.491(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C9 N2 1.332(2) . ?
C9 C11 1.481(3) . ?
C17 C20 1.371(3) . ?
C17 N3 1.467(3) . ?
C6 C1 1.382(3) . ?
C6 C5 1.386(3) . ?
C6 N1 1.410(2) . ?
C11 O2 1.192(2) . ?
C11 O3 1.315(2) . ?
C20 H20 0.9300 . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
N3 O5 1.216(3) . ?
N3 O4 1.221(3) . ?
C5 O1 1.375(3) . ?
C5 C4 1.383(3) . ?
C7 O1 1.433(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C12 C13 1.437(4) . ?
C12 O3 1.445(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 N2 1.338(2) . ?

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
C8 C10 C9 103.63(15) . . ?
C8 C10 C18 126.46(16) . . ?
C9 C10 C18 129.83(16) . . ?
C19 C18 C15 119.96(16) . . ?
C19 C18 C10 118.07(16) . . ?
C15 C18 C10 121.96(16) . . ?
C16 C15 C18 118.27(17) . . ?
C16 C15 C14 119.92(18) . . ?
C18 C15 C14 121.81(18) . . ?
N1 C8 C10 106.88(16) . . ?
N1 C8 C7 117.57(16) . . ?
C10 C8 C7 135.50(17) . . ?
C17 C16 C15 120.17(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C20 C19 C18 121.17(18) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
N2 C9 C10 112.40(16) . . ?
N2 C9 C11 117.32(15) . . ?
C10 C9 C11 130.26(17) . . ?
C20 C17 C16 122.22(18) . . ?
C20 C17 N3 118.8(2) . . ?
C16 C17 N3 119.00(19) . . ?
C1 C6 C5 121.55(18) . . ?
C1 C6 N1 122.21(18) . . ?
C5 C6 N1 116.18(17) . . ?
O2 C11 O3 124.19(19) . . ?
O2 C11 C9 124.67(19) . . ?
O3 C11 C9 111.13(15) . . ?
C17 C20 C19 118.04(18) . . ?
C17 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C2 C1 C6 119.2(2) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
O5 N3 O4 123.4(2) . . ?
O5 N3 C17 118.6(2) . . ?
O4 N3 C17 118.0(2) . . ?
O1 C5 C4 119.0(2) . . ?
O1 C5 C6 122.16(18) . . ?
C4 C5 C6 118.7(2) . . ?
O1 C7 C8 111.61(16) . . ?
O1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
O1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C2 C3 119.6(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C13 C12 O3 108.3(2) . . ?
C13 C12 H12A 110.0 . . ?
O3 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
O3 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O3 C12 118.33(16) . . ?
C5 O1 C7 116.17(16) . . ?
N2 N1 C8 113.54(15) . . ?
N2 N1 C6 123.58(15) . . ?
C8 N1 C6 122.71(16) . . ?
C9 N2 N1 103.54(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.041