# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_publication_text
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_publ_contact_author_name        'Vishnu Ji Ram'
_publ_contact_author_address     
;Department of Chemistry
University of Lucknow
Lucknow 226 007
India
;
_publ_contact_author_email       vjiram@yahoo.com
loop_
_publ_author_name
_publ_author_address
'Hardesh K. Maurya'
;Department of Chemistry
University of Lucknow
Lucknow 226 007
India
;
'Sanjay K. Gautam'
;Department of Chemistry
University of Lucknow
Lucknow 226 007
India
;
'Abhinav Kumar'
;Department of Chemistry
University of Lucknow
Lucknow 226 007
India
;
'Visnhu K. Tandon'
;Department of Chemistry
University of Lucknow
Lucknow 226 007
India
;
'Ramendra Pratap'
;Department of Chemistry
University of Delhi
New Delhi 110 007
India
;

data_sh3147
_database_code_depnum_ccdc_archive 'CCDC 859071'
#TrackingRef '- 6. X-ray data 12f (sh3147).cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N3 O3'
_chemical_formula_weight         385.41

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   P2(1)/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                   14.605(4)
_cell_length_b                   6.1389(17)
_cell_length_c                   20.396(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.627(18)
_cell_angle_gamma                90.00
_cell_volume                     1828.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3328
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.59

_exptl_crystal_description       Plate
_exptl_crystal_colour            'transparent brownish'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   'SADABS BrukerAXS 2010'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15040
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3937
_reflns_number_gt                2791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0473P)^2^+0.3826P] 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         3937
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O1 O 0.20405(7) 1.09781(17) 0.33635(5) 0.0269(3) Uani 1 1 d . . .
O2 O 0.08975(8) 0.9377(2) 0.28235(6) 0.0418(3) Uani 1 1 d . . .
O3 O 0.45339(7) 1.19160(18) 0.45040(5) 0.0307(3) Uani 1 1 d . . .
N1 N 0.20679(8) 0.6490(2) 0.48687(6) 0.0233(3) Uani 1 1 d . . .
N2 N 0.08665(9) 0.4426(2) 0.43301(6) 0.0261(3) Uani 1 1 d . . .
N3 N 0.02784(10) 0.5411(3) 0.33114(7) 0.0341(4) Uani 1 1 d . . .
C1 C 0.20443(10) 0.7929(2) 0.43630(7) 0.0221(3) Uani 1 1 d . . .
C2 C 0.14618(10) 0.4852(2) 0.48321(7) 0.0235(3) Uani 1 1 d . . .
C3 C 0.08435(10) 0.5852(3) 0.38235(7) 0.0248(3) Uani 1 1 d . . .
C4 C 0.14193(10) 0.7732(2) 0.38314(7) 0.0235(3) Uani 1 1 d . . .
C5 C 0.14031(10) 0.9332(3) 0.33109(7) 0.0276(4) Uani 1 1 d . . .
C6 C 0.26984(10) 1.1146(2) 0.38731(7) 0.0224(3) Uani 1 1 d . . .
C7 C 0.33154(10) 1.2987(2) 0.37193(7) 0.0238(3) Uani 1 1 d . . .
C8 C 0.30644(11) 1.4509(3) 0.32210(7) 0.0248(3) Uani 1 1 d . . .
C9 C 0.36364(11) 1.6171(3) 0.30143(7) 0.0260(4) Uani 1 1 d . . .
C10 C 0.45169(11) 1.6350(3) 0.33085(7) 0.0271(4) Uani 1 1 d . . .
C11 C 0.47715(11) 1.4874(3) 0.37992(8) 0.0281(4) Uani 1 1 d . . .
C12 C 0.41893(11) 1.3244(2) 0.40114(7) 0.0251(3) Uani 1 1 d . . .
C13 C 0.39362(12) 1.1680(3) 0.50592(8) 0.0289(4) Uani 1 1 d . . .
C14 C 0.33446(12) 0.9698(3) 0.49786(8) 0.0275(4) Uani 1 1 d . . .
C15 C 0.27055(10) 0.9698(2) 0.43809(7) 0.0227(3) Uani 1 1 d . . .
C16 C 0.14562(10) 0.3350(2) 0.54115(7) 0.0239(3) Uani 1 1 d . . .
C17 C 0.19424(11) 0.3870(3) 0.59957(8) 0.0295(4) Uani 1 1 d . . .
C18 C 0.19170(12) 0.2475(3) 0.65383(8) 0.0349(4) Uani 1 1 d . . .
C19 C 0.14148(12) 0.0557(3) 0.65024(9) 0.0363(4) Uani 1 1 d . . .
C20 C 0.09377(12) 0.0011(3) 0.59235(8) 0.0338(4) Uani 1 1 d . . .
C21 C 0.09579(11) 0.1408(3) 0.53819(8) 0.0289(4) Uani 1 1 d . . .
C22 C 0.33426(14) 1.7705(3) 0.24649(9) 0.0347(4) Uani 1 1 d . . .
C23 C 0.51753(14) 1.8082(3) 0.30904(10) 0.0369(4) Uani 1 1 d . . .
H1 H 0.2462(11) 1.436(2) 0.3013(7) 0.022(4) Uiso 1 1 d . . .
H2 H 0.5380(12) 1.500(3) 0.4018(8) 0.039(5) Uiso 1 1 d . . .
H3 H 0.3578(11) 1.312(3) 0.5097(8) 0.029(4) Uiso 1 1 d . . .
H4 H 0.4348(10) 1.149(2) 0.5456(8) 0.025(4) Uiso 1 1 d . . .
H5 H 0.2966(12) 0.955(3) 0.5384(9) 0.036(5) Uiso 1 1 d . . .
H6 H 0.3737(11) 0.834(3) 0.4969(8) 0.033(5) Uiso 1 1 d . . .
H7 H 0.2276(12) 0.526(3) 0.6007(8) 0.037(5) Uiso 1 1 d . . .
H8 H 0.2241(12) 0.286(3) 0.6938(9) 0.040(5) Uiso 1 1 d . . .
H9 H 0.1390(11) -0.043(3) 0.6881(8) 0.031(4) Uiso 1 1 d . . .
H10 H 0.0570(12) -0.134(3) 0.5874(9) 0.045(5) Uiso 1 1 d . . .
H11 H 0.0620(11) 0.104(3) 0.4966(8) 0.032(4) Uiso 1 1 d . . .
H12 H 0.0208(12) 0.639(3) 0.2994(9) 0.039(5) Uiso 1 1 d . . .
H13 H -0.0117(14) 0.418(4) 0.3335(9) 0.054(6) Uiso 1 1 d . . .
H14 H 0.2704(14) 1.746(3) 0.2339(9) 0.045(5) Uiso 1 1 d . . .
H15 H 0.3450(13) 1.924(3) 0.2584(9) 0.046(5) Uiso 1 1 d . . .
H16 H 0.3726(14) 1.743(3) 0.2040(10) 0.057(6) Uiso 1 1 d . . .
H17 H 0.5277(13) 1.801(3) 0.2602(11) 0.059(6) Uiso 1 1 d . . .
H18 H 0.4946(14) 1.955(4) 0.3201(10) 0.062(7) Uiso 1 1 d . . .
H19 H 0.5785(14) 1.793(3) 0.3330(9) 0.050(6) Uiso 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
O1 0.0247(6) 0.0341(6) 0.0214(6) 0.0045(5) -0.0069(4) -0.0044(5)
O2 0.0363(7) 0.0584(8) 0.0295(7) 0.0151(6) -0.0165(5) -0.0154(6)
O3 0.0263(6) 0.0348(6) 0.0307(6) 0.0071(5) -0.0062(5) -0.0026(5)
N1 0.0245(7) 0.0247(7) 0.0207(6) 0.0002(5) -0.0029(5) -0.0021(6)
N2 0.0262(7) 0.0308(7) 0.0211(7) 0.0003(5) -0.0039(5) -0.0038(6)
N3 0.0342(8) 0.0419(9) 0.0253(8) 0.0041(7) -0.0120(6) -0.0120(7)
C1 0.0220(7) 0.0253(8) 0.0188(7) -0.0024(6) 0.0002(6) 0.0016(7)
C2 0.0223(8) 0.0265(8) 0.0215(8) -0.0029(6) -0.0014(6) 0.0006(7)
C3 0.0205(8) 0.0330(9) 0.0207(8) -0.0028(7) -0.0021(6) -0.0013(7)
C4 0.0208(8) 0.0308(8) 0.0188(7) -0.0005(6) -0.0016(6) -0.0001(7)
C5 0.0226(8) 0.0364(9) 0.0235(8) 0.0021(7) -0.0024(6) -0.0037(7)
C6 0.0199(7) 0.0281(8) 0.0190(7) -0.0036(6) -0.0034(6) 0.0016(7)
C7 0.0259(8) 0.0244(8) 0.0210(8) -0.0016(6) 0.0009(6) 0.0000(7)
C8 0.0251(8) 0.0285(8) 0.0207(8) -0.0025(6) 0.0009(6) 0.0032(7)
C9 0.0321(9) 0.0242(8) 0.0221(8) -0.0021(6) 0.0040(6) 0.0020(7)
C10 0.0338(9) 0.0263(8) 0.0213(8) -0.0033(6) 0.0032(7) -0.0037(7)
C11 0.0275(9) 0.0321(9) 0.0246(8) -0.0055(7) -0.0013(7) -0.0041(7)
C12 0.0276(8) 0.0255(8) 0.0221(8) -0.0010(6) -0.0022(6) -0.0002(7)
C13 0.0320(9) 0.0323(9) 0.0218(8) 0.0015(7) -0.0087(7) -0.0060(8)
C14 0.0294(9) 0.0305(9) 0.0221(8) 0.0032(7) -0.0074(7) -0.0050(8)
C15 0.0226(8) 0.0265(8) 0.0188(7) -0.0007(6) -0.0030(6) 0.0004(7)
C16 0.0229(8) 0.0266(8) 0.0220(8) 0.0007(6) -0.0005(6) 0.0021(7)
C17 0.0300(9) 0.0333(9) 0.0249(8) 0.0017(7) -0.0032(7) -0.0041(8)
C18 0.0374(10) 0.0430(11) 0.0238(9) 0.0033(8) -0.0070(7) -0.0038(8)
C19 0.0382(10) 0.0403(10) 0.0301(9) 0.0123(8) -0.0028(7) 0.0003(8)
C20 0.0353(10) 0.0302(9) 0.0357(10) 0.0057(7) -0.0007(8) -0.0050(8)
C21 0.0287(9) 0.0317(9) 0.0260(9) 0.0002(7) -0.0029(7) -0.0016(7)
C22 0.0387(11) 0.0325(10) 0.0329(10) 0.0063(8) 0.0013(8) -0.0004(8)
C23 0.0410(11) 0.0370(11) 0.0326(10) 0.0018(8) 0.0018(8) -0.0105(9)

_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
O1 C5 1.3760(18) . ?
O1 C6 1.3992(16) . ?
O2 C5 1.2217(18) . ?
O3 C12 1.3779(18) . ?
O3 C13 1.457(2) . ?
N1 C2 1.3404(19) . ?
N1 C1 1.3578(19) . ?
N2 C2 1.3497(19) . ?
N2 C3 1.354(2) . ?
N3 C3 1.3405(19) . ?
N3 H12 0.888(19) . ?
N3 H13 0.95(2) . ?
C1 C4 1.403(2) . ?
C1 C15 1.453(2) . ?
C2 C16 1.499(2) . ?
C3 C4 1.427(2) . ?
C4 C5 1.446(2) . ?
C6 C15 1.365(2) . ?
C6 C7 1.484(2) . ?
C7 C12 1.402(2) . ?
C7 C8 1.421(2) . ?
C8 C9 1.392(2) . ?
C8 H1 0.971(15) . ?
C9 C10 1.408(2) . ?
C9 C22 1.517(2) . ?
C10 C11 1.393(2) . ?
C10 C23 1.509(2) . ?
C11 C12 1.390(2) . ?
C11 H2 0.986(18) . ?
C13 C14 1.499(2) . ?
C13 H3 1.029(16) . ?
C13 H4 1.001(15) . ?
C14 C15 1.514(2) . ?
C14 H5 1.011(18) . ?
C14 H6 1.013(18) . ?
C16 C21 1.397(2) . ?
C16 C17 1.406(2) . ?
C17 C18 1.401(2) . ?
C17 H7 0.980(18) . ?
C18 C19 1.388(2) . ?
C18 H8 0.962(18) . ?
C19 C20 1.395(2) . ?
C19 H9 0.982(17) . ?
C20 C21 1.399(2) . ?
C20 H10 0.99(2) . ?
C21 H11 0.995(17) . ?
C22 H14 0.972(19) . ?
C22 H15 0.99(2) . ?
C22 H16 1.06(2) . ?
C23 H17 1.01(2) . ?
C23 H18 0.99(2) . ?
C23 H19 1.01(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
C5 O1 C6 124.12(11) . . ?
C12 O3 C13 114.27(12) . . ?
C2 N1 C1 116.33(12) . . ?
C2 N2 C3 117.09(13) . . ?
C3 N3 H12 119.1(12) . . ?
C3 N3 H13 118.8(12) . . ?
H12 N3 H13 121.1(17) . . ?
N1 C1 C4 122.19(13) . . ?
N1 C1 C15 117.70(13) . . ?
C4 C1 C15 120.10(13) . . ?
N1 C2 N2 126.68(14) . . ?
N1 C2 C16 115.85(13) . . ?
N2 C2 C16 117.47(13) . . ?
N3 C3 N2 117.73(14) . . ?
N3 C3 C4 121.44(14) . . ?
N2 C3 C4 120.81(13) . . ?
C1 C4 C3 116.67(13) . . ?
C1 C4 C5 120.35(14) . . ?
C3 C4 C5 122.93(13) . . ?
O2 C5 O1 116.03(14) . . ?
O2 C5 C4 127.55(14) . . ?
O1 C5 C4 116.41(13) . . ?
C15 C6 O1 120.40(13) . . ?
C15 C6 C7 131.65(13) . . ?
O1 C6 C7 107.91(12) . . ?
C12 C7 C8 116.30(14) . . ?
C12 C7 C6 123.15(13) . . ?
C8 C7 C6 120.39(13) . . ?
C9 C8 C7 123.64(15) . . ?
C9 C8 H1 118.8(9) . . ?
C7 C8 H1 117.5(9) . . ?
C8 C9 C10 118.49(14) . . ?
C8 C9 C22 121.30(15) . . ?
C10 C9 C22 120.16(15) . . ?
C11 C10 C9 118.53(15) . . ?
C11 C10 C23 120.72(15) . . ?
C9 C10 C23 120.74(15) . . ?
C12 C11 C10 122.60(15) . . ?
C12 C11 H2 117.7(10) . . ?
C10 C11 H2 119.6(10) . . ?
O3 C12 C11 116.03(14) . . ?
O3 C12 C7 123.53(14) . . ?
C11 C12 C7 120.42(14) . . ?
O3 C13 C14 110.59(13) . . ?
O3 C13 H3 106.9(9) . . ?
C14 C13 H3 114.3(9) . . ?
O3 C13 H4 106.3(9) . . ?
C14 C13 H4 109.0(9) . . ?
H3 C13 H4 109.4(13) . . ?
C13 C14 C15 115.36(13) . . ?
C13 C14 H5 108.0(10) . . ?
C15 C14 H5 108.6(10) . . ?
C13 C14 H6 110.3(9) . . ?
C15 C14 H6 108.7(9) . . ?
H5 C14 H6 105.4(13) . . ?
C6 C15 C1 118.49(13) . . ?
C6 C15 C14 127.05(14) . . ?
C1 C15 C14 114.46(13) . . ?
C21 C16 C17 118.69(14) . . ?
C21 C16 C2 120.35(13) . . ?
C17 C16 C2 120.95(14) . . ?
C18 C17 C16 120.43(16) . . ?
C18 C17 H7 122.5(10) . . ?
C16 C17 H7 117.1(10) . . ?
C19 C18 C17 120.19(16) . . ?
C19 C18 H8 120.1(11) . . ?
C17 C18 H8 119.7(11) . . ?
C18 C19 C20 119.92(16) . . ?
C18 C19 H9 120.8(10) . . ?
C20 C19 H9 119.3(10) . . ?
C19 C20 C21 120.00(16) . . ?
C19 C20 H10 123.0(10) . . ?
C21 C20 H10 117.0(11) . . ?
C16 C21 C20 120.76(15) . . ?
C16 C21 H11 118.5(10) . . ?
C20 C21 H11 120.8(10) . . ?
C9 C22 H14 110.5(11) . . ?
C9 C22 H15 111.9(11) . . ?
H14 C22 H15 110.8(16) . . ?
C9 C22 H16 111.1(11) . . ?
H14 C22 H16 106.6(15) . . ?
H15 C22 H16 105.8(16) . . ?
C10 C23 H17 111.7(12) . . ?
C10 C23 H18 110.6(12) . . ?
H17 C23 H18 109.1(16) . . ?
C10 C23 H19 110.6(11) . . ?
H17 C23 H19 108.7(16) . . ?
H18 C23 H19 106.1(16) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041