# 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_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
D.Maiti
P.Pandit
N.Chatterjee
_publ_contact_author_name        'Palash Pandit'
_publ_contact_author_email       palashpandit@gmail.com

data_pp391_0m
_database_code_depnum_ccdc_archive 'CCDC 773893'
#TrackingRef '- CIF 773893.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44

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                   8.752(6)
_cell_length_b                   10.838(8)
_cell_length_c                   11.416(8)
_cell_angle_alpha                69.727(9)
_cell_angle_beta                 85.757(9)
_cell_angle_gamma                85.893(8)
_cell_volume                     1011.8(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2537
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.52

_exptl_crystal_description       square
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            7442
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3808
_reflns_number_gt                2636
_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^)+(0.1075P)^2^+0.0321P] 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         3808
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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
N1 N 0.41898(16) 0.80582(15) 0.24229(14) 0.0532(4) Uani 1 1 d . . .
O1 O -0.01842(15) 0.81002(14) 0.37013(16) 0.0751(5) Uani 1 1 d . . .
O2 O 0.65103(17) 1.00452(18) 0.18335(16) 0.0840(5) Uani 1 1 d . . .
O3 O 0.48712(14) 1.07731(12) 0.30990(11) 0.0550(4) Uani 1 1 d . . .
C1 C 0.2125(2) 0.67295(17) 0.37060(17) 0.0510(4) Uani 1 1 d . . .
C2 C 0.3014(2) 0.56302(19) 0.4402(2) 0.0637(5) Uani 1 1 d . . .
C3 C 0.2586(3) 0.4901(2) 0.5625(2) 0.0749(7) Uani 1 1 d . . .
C4 C 0.1279(3) 0.5262(3) 0.6184(2) 0.0771(7) Uani 1 1 d . . .
C5 C 0.0378(3) 0.6323(2) 0.5531(2) 0.0709(6) Uani 1 1 d . . .
C6 C 0.0792(2) 0.70582(18) 0.42794(19) 0.0567(5) Uani 1 1 d . . .
C7 C -0.0048(2) 0.8541(2) 0.2364(3) 0.0738(6) Uani 1 1 d . . .
C8 C 0.1594(2) 0.87953(18) 0.1880(2) 0.0553(5) Uani 1 1 d . . .
C9 C 0.2654(2) 0.75492(18) 0.23755(17) 0.0524(4) Uani 1 1 d . . .
C10 C 0.23429(19) 0.98128(16) 0.22756(17) 0.0478(4) Uani 1 1 d . . .
C11 C 0.39766(19) 0.92478(17) 0.23625(15) 0.0467(4) Uani 1 1 d . . .
C12 C 0.5297(2) 1.00490(18) 0.23974(16) 0.0526(5) Uani 1 1 d . . .
C13 C 0.2832(2) 1.1655(2) 0.02319(19) 0.0637(5) Uani 1 1 d . . .
C14 C 0.21567(19) 1.12384(17) 0.14317(16) 0.0497(4) Uani 1 1 d . . .
C15 C 0.1357(3) 1.2155(2) 0.1849(2) 0.0687(6) Uani 1 1 d . . .
C16 C 0.1252(3) 1.3471(2) 0.1103(3) 0.0926(8) Uani 1 1 d . . .
C17 C 0.1938(3) 1.3866(3) -0.0082(3) 0.0932(8) Uani 1 1 d . . .
C18 C 0.2730(3) 1.2969(3) -0.0512(2) 0.0803(7) Uani 1 1 d . . .
C19 C 0.2809(3) 0.6741(3) 0.1508(3) 0.0757(7) Uani 1 1 d . . .
C20 C 0.5875(3) 1.1747(2) 0.32649(18) 0.0702(6) Uani 1 1 d . . .
C21 C 0.7244(4) 1.1008(4) 0.3978(3) 0.0957(9) Uani 1 1 d . . .
C22 C 0.4853(5) 1.2348(3) 0.4068(4) 0.0995(10) Uani 1 1 d . . .
C23 C 0.6293(7) 1.2751(4) 0.2010(3) 0.1231(15) Uani 1 1 d . . .
H1 H 0.093(3) 1.183(2) 0.270(2) 0.081(7) Uiso 1 1 d . . .
H2 H 0.061(4) 1.415(3) 0.138(3) 0.122(10) Uiso 1 1 d . . .
H3 H 0.187(3) 1.482(3) -0.053(3) 0.117(9) Uiso 1 1 d . . .
H4 H 0.318(3) 1.324(3) -0.135(3) 0.108(9) Uiso 1 1 d . . .
H5 H 0.336(2) 1.102(2) -0.0099(19) 0.067(6) Uiso 1 1 d . . .
H6 H -0.051(3) 0.664(2) 0.583(2) 0.075(7) Uiso 1 1 d . . .
H7 H 0.095(3) 0.465(2) 0.711(2) 0.089(7) Uiso 1 1 d . . .
H8 H 0.319(3) 0.420(3) 0.603(2) 0.086(8) Uiso 1 1 d . . .
H9 H 0.399(2) 0.5386(19) 0.3962(18) 0.066(6) Uiso 1 1 d . . .
H10 H 0.524(4) 1.312(3) 0.158(3) 0.136(14) Uiso 1 1 d . . .
H11 H 0.705(4) 1.231(3) 0.160(3) 0.115(12) Uiso 1 1 d . . .
H12 H 0.686(3) 1.342(3) 0.217(3) 0.118(9) Uiso 1 1 d . . .
H13 H 0.794(4) 1.070(3) 0.343(3) 0.125(12) Uiso 1 1 d . . .
H14 H 0.787(4) 1.167(3) 0.413(3) 0.122(10) Uiso 1 1 d . . .
H15 H 0.539(3) 1.305(3) 0.421(3) 0.111(9) Uiso 1 1 d . . .
H16 H 0.453(4) 1.168(4) 0.482(4) 0.140(13) Uiso 1 1 d . . .
H17 H 0.332(3) 0.727(3) 0.067(3) 0.100(8) Uiso 1 1 d . . .
H18 H 0.341(3) 0.592(3) 0.184(2) 0.093(8) Uiso 1 1 d . . .
H19 H 0.176(3) 0.649(3) 0.138(2) 0.095(8) Uiso 1 1 d . . .
H20 H -0.071(2) 0.936(2) 0.209(2) 0.070(6) Uiso 1 1 d . . .
H21 H -0.042(3) 0.780(3) 0.202(2) 0.101(8) Uiso 1 1 d . . .
H22 H 0.187(2) 0.9765(18) 0.3173(18) 0.056(5) Uiso 1 1 d . . .
H23 H 0.161(2) 0.907(2) 0.095(2) 0.071(6) Uiso 1 1 d . . .
H24 H 0.693(4) 1.029(3) 0.485(3) 0.125(10) Uiso 1 1 d . . .
H25 H 0.405(4) 1.285(4) 0.353(4) 0.147(15) 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
N1 0.0499(8) 0.0571(9) 0.0584(9) -0.0266(7) -0.0022(7) -0.0064(7)
O1 0.0529(8) 0.0676(9) 0.1039(12) -0.0306(9) 0.0080(8) -0.0033(7)
O2 0.0551(9) 0.1234(14) 0.0986(12) -0.0690(11) 0.0120(8) -0.0260(8)
O3 0.0632(8) 0.0564(7) 0.0520(7) -0.0242(6) -0.0005(6) -0.0207(6)
C1 0.0493(10) 0.0481(10) 0.0634(11) -0.0268(8) -0.0065(8) -0.0102(8)
C2 0.0568(12) 0.0561(11) 0.0801(14) -0.0231(11) -0.0121(10) -0.0077(9)
C3 0.0792(16) 0.0601(13) 0.0805(16) -0.0106(12) -0.0252(13) -0.0188(12)
C4 0.0905(18) 0.0762(15) 0.0692(14) -0.0243(13) -0.0071(13) -0.0350(13)
C5 0.0697(14) 0.0767(15) 0.0802(15) -0.0431(13) 0.0122(12) -0.0279(12)
C6 0.0508(10) 0.0537(10) 0.0752(13) -0.0325(10) -0.0019(9) -0.0122(8)
C7 0.0528(12) 0.0663(14) 0.1041(19) -0.0272(13) -0.0254(12) -0.0024(10)
C8 0.0572(11) 0.0538(11) 0.0598(12) -0.0219(9) -0.0159(9) -0.0082(8)
C9 0.0528(10) 0.0521(10) 0.0609(11) -0.0284(9) -0.0073(8) -0.0075(8)
C10 0.0489(10) 0.0474(10) 0.0496(10) -0.0187(8) -0.0054(8) -0.0053(7)
C11 0.0503(10) 0.0497(10) 0.0453(9) -0.0220(8) -0.0046(7) -0.0060(7)
C12 0.0511(10) 0.0611(11) 0.0506(10) -0.0238(9) -0.0068(8) -0.0077(8)
C13 0.0637(12) 0.0714(13) 0.0533(11) -0.0190(10) -0.0024(9) 0.0014(10)
C14 0.0467(9) 0.0512(10) 0.0520(10) -0.0181(8) -0.0029(8) -0.0048(7)
C15 0.0756(14) 0.0549(12) 0.0703(14) -0.0181(10) 0.0097(11) 0.0000(10)
C16 0.1019(19) 0.0540(13) 0.111(2) -0.0210(14) 0.0126(16) 0.0104(13)
C17 0.0934(18) 0.0586(15) 0.101(2) 0.0056(14) -0.0042(15) -0.0029(13)
C18 0.0745(15) 0.0854(17) 0.0608(14) 0.0008(12) -0.0015(11) -0.0073(13)
C19 0.0909(18) 0.0717(15) 0.0823(16) -0.0473(13) 0.0005(14) -0.0176(14)
C20 0.0998(16) 0.0638(12) 0.0531(11) -0.0205(9) -0.0023(11) -0.0443(11)
C21 0.0907(19) 0.129(2) 0.0845(19) -0.0484(19) -0.0111(15) -0.0484(18)
C22 0.144(3) 0.0779(18) 0.097(2) -0.0517(18) -0.001(2) -0.035(2)
C23 0.198(5) 0.099(2) 0.0700(18) -0.0117(17) 0.002(2) -0.087(3)

_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
N1 C11 1.268(2) . ?
N1 C9 1.501(2) . ?
O1 C6 1.367(3) . ?
O1 C7 1.431(3) . ?
O2 C12 1.201(2) . ?
O3 C12 1.321(2) . ?
O3 C20 1.489(2) . ?
C1 C6 1.381(3) . ?
C1 C2 1.399(3) . ?
C1 C9 1.527(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.368(4) . ?
C4 C5 1.365(4) . ?
C5 C6 1.408(3) . ?
C7 C8 1.511(3) . ?
C8 C10 1.531(3) . ?
C8 C9 1.540(3) . ?
C9 C19 1.527(3) . ?
C10 C11 1.511(3) . ?
C10 C14 1.516(3) . ?
C11 C12 1.505(3) . ?
C13 C18 1.383(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.361(4) . ?
C20 C23 1.507(3) . ?
C20 C22 1.509(4) . ?
C20 C21 1.515(4) . ?

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
C11 N1 C9 107.65(14) . . ?
C6 O1 C7 114.46(16) . . ?
C12 O3 C20 122.75(15) . . ?
C6 C1 C2 117.62(19) . . ?
C6 C1 C9 121.88(17) . . ?
C2 C1 C9 120.48(17) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 119.9(2) . . ?
C5 C4 C3 120.2(2) . . ?
C4 C5 C6 120.3(2) . . ?
O1 C6 C1 123.47(19) . . ?
O1 C6 C5 116.04(19) . . ?
C1 C6 C5 120.5(2) . . ?
O1 C7 C8 111.55(17) . . ?
C7 C8 C10 114.95(17) . . ?
C7 C8 C9 111.76(17) . . ?
C10 C8 C9 103.55(15) . . ?
N1 C9 C19 108.75(17) . . ?
N1 C9 C1 108.09(14) . . ?
C19 C9 C1 112.05(18) . . ?
N1 C9 C8 104.58(15) . . ?
C19 C9 C8 112.69(19) . . ?
C1 C9 C8 110.30(15) . . ?
C11 C10 C14 114.64(14) . . ?
C11 C10 C8 99.60(14) . . ?
C14 C10 C8 116.72(15) . . ?
N1 C11 C12 121.13(16) . . ?
N1 C11 C10 117.10(15) . . ?
C12 C11 C10 121.76(16) . . ?
O2 C12 O3 126.81(17) . . ?
O2 C12 C11 124.27(17) . . ?
O3 C12 C11 108.87(15) . . ?
C18 C13 C14 120.6(2) . . ?
C15 C14 C13 118.38(18) . . ?
C15 C14 C10 120.91(17) . . ?
C13 C14 C10 120.68(17) . . ?
C14 C15 C16 121.0(2) . . ?
C17 C16 C15 119.7(2) . . ?
C18 C17 C16 120.0(2) . . ?
C17 C18 C13 120.3(2) . . ?
O3 C20 C23 109.67(19) . . ?
O3 C20 C22 102.18(19) . . ?
C23 C20 C22 111.7(3) . . ?
O3 C20 C21 108.52(19) . . ?
C23 C20 C21 114.0(3) . . ?
C22 C20 C21 110.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034