# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#  experimental, refinement, atomic coordinates, 
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data_cm00301_0m
_database_code_depnum_ccdc_archive 'CCDC 898030'
#TrackingRef '13498_web_deposit_cif_file_0_Dr.ChandanMukherjee_1345780274.cm00301_0m.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N2 O'
_chemical_formula_sum            'C21 H24 N2 O'
_chemical_formula_weight         320.42
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'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a                   34.3374(12)
_cell_length_b                   6.0181(2)
_cell_length_c                   18.6307(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.012(2)
_cell_angle_gamma                90.00
_cell_volume                     3735.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(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          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.987
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20752
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3093
_reflns_number_gt                2306
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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^ > 2\s(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^)+(0.1701P)^2^+4.5130P] 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         3093
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2862
_refine_ls_wR_factor_gt          0.2631
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.372
_refine_ls_shift/su_mean         0.010
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
C12 C 0.11243(9) 0.1382(5) 0.29665(15) 0.0501(8) Uani 1 1 d . . .
C8 C 0.16296(9) 0.3533(5) 0.38188(16) 0.0530(8) Uani 1 1 d . . .
C13 C 0.15200(9) 0.2013(5) 0.32434(16) 0.0509(8) Uani 1 1 d . . .
C6 C 0.23248(10) 0.3032(5) 0.38268(16) 0.0532(8) Uani 1 1 d . . .
C10 C 0.09477(9) 0.3718(5) 0.39221(16) 0.0524(8) Uani 1 1 d . . .
C9 C 0.13438(9) 0.4333(5) 0.41616(16) 0.0538(8) Uani 1 1 d . . .
H9 H 0.1420 0.5301 0.4560 0.065 Uiso 1 1 calc R . .
C11 C 0.08463(10) 0.2264(5) 0.33258(16) 0.0535(8) Uani 1 1 d . . .
H11 H 0.0578 0.1857 0.3157 0.064 Uiso 1 1 calc R . .
C5 C 0.27332(10) 0.3337(5) 0.41239(17) 0.0568(8) Uani 1 1 d . . .
C1 C 0.22080(10) 0.1399(5) 0.32812(17) 0.0537(8) Uani 1 1 d . . .
C2 C 0.24836(11) 0.0068(6) 0.30743(19) 0.0631(9) Uani 1 1 d . . .
H2 H 0.2399 -0.1043 0.2724 0.076 Uiso 1 1 calc R . .
C7 C 0.28644(10) 0.5061(6) 0.4660(2) 0.0636(9) Uani 1 1 d . . .
C4 C 0.30171(11) 0.2016(6) 0.3896(2) 0.0690(10) Uani 1 1 d . . .
H4 H 0.3290 0.2256 0.4091 0.083 Uiso 1 1 calc R . .
C3 C 0.28912(12) 0.0371(6) 0.3386(2) 0.0716(10) Uani 1 1 d . . .
H3 H 0.3078 -0.0545 0.3247 0.086 Uiso 1 1 calc R . .
C14 C 0.09982(10) -0.0115(5) 0.22780(16) 0.0572(9) Uani 1 1 d . . .
C16 C 0.11984(13) -0.2387(6) 0.2412(2) 0.0767(11) Uani 1 1 d . . .
H16A H 0.1485 -0.2208 0.2536 0.115 Uiso 1 1 calc R . .
H16B H 0.1118 -0.3274 0.1973 0.115 Uiso 1 1 calc R . .
H16C H 0.1119 -0.3112 0.2813 0.115 Uiso 1 1 calc R . .
C17 C 0.11171(16) 0.1018(7) 0.16286(19) 0.0912(14) Uani 1 1 d . . .
H17A H 0.1000 0.2475 0.1558 0.137 Uiso 1 1 calc R . .
H17B H 0.1022 0.0152 0.1188 0.137 Uiso 1 1 calc R . .
H17C H 0.1404 0.1138 0.1732 0.137 Uiso 1 1 calc R . .
C15 C 0.05461(12) -0.0501(9) 0.2071(2) 0.0972(15) Uani 1 1 d . . .
H15A H 0.0467 -0.1210 0.2475 0.146 Uiso 1 1 calc R . .
H15B H 0.0476 -0.1435 0.1641 0.146 Uiso 1 1 calc R . .
H15C H 0.0410 0.0898 0.1966 0.146 Uiso 1 1 calc R . .
C18 C 0.06320(10) 0.4583(6) 0.43153(18) 0.0632(9) Uani 1 1 d . . .
C20 C 0.0247(2) 0.473(2) 0.3838(5) 0.285(8) Uani 1 1 d . . .
H20A H 0.0218 0.6142 0.3589 0.428 Uiso 1 1 calc R . .
H20B H 0.0048 0.4601 0.4120 0.428 Uiso 1 1 calc R . .
H20C H 0.0211 0.3558 0.3479 0.428 Uiso 1 1 calc R . .
C19 C 0.0720(3) 0.6818(16) 0.4590(8) 0.308(9) Uani 1 1 d . . .
H19A H 0.0890 0.7534 0.4319 0.462 Uiso 1 1 calc R . .
H19B H 0.0855 0.6767 0.5105 0.462 Uiso 1 1 calc R . .
H19C H 0.0474 0.7638 0.4528 0.462 Uiso 1 1 calc R . .
C21 C 0.0622(4) 0.324(2) 0.4918(7) 0.378(12) Uani 1 1 d . . .
H21A H 0.0589 0.4146 0.5322 0.567 Uiso 1 1 calc R . .
H21B H 0.0869 0.2425 0.5064 0.567 Uiso 1 1 calc R . .
H21C H 0.0402 0.2216 0.4783 0.567 Uiso 1 1 calc R . .
N1 N 0.20295(8) 0.4243(5) 0.40343(17) 0.0688(9) Uani 1 1 d . . .
N2 N 0.29567(10) 0.6465(6) 0.5078(2) 0.0880(11) Uani 1 1 d . . .
O1 O 0.18119(7) 0.1190(4) 0.29101(13) 0.0710(8) Uani 1 1 d . . .
H1N H 0.2098(12) 0.539(8) 0.438(2) 0.091(12) 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
C12 0.057(2) 0.0477(15) 0.0427(15) -0.0019(12) 0.0073(14) -0.0040(13)
C8 0.049(2) 0.0569(17) 0.0513(17) -0.0119(13) 0.0090(14) -0.0036(13)
C13 0.052(2) 0.0562(17) 0.0460(15) -0.0079(13) 0.0143(14) 0.0003(13)
C6 0.054(2) 0.0538(17) 0.0545(17) -0.0034(13) 0.0175(15) -0.0008(13)
C10 0.051(2) 0.0560(17) 0.0498(16) -0.0009(13) 0.0122(14) 0.0040(13)
C9 0.053(2) 0.0587(17) 0.0471(16) -0.0114(13) 0.0082(14) 0.0028(14)
C11 0.0473(19) 0.0588(18) 0.0521(17) -0.0013(13) 0.0077(14) -0.0016(13)
C5 0.051(2) 0.0603(18) 0.0587(18) 0.0000(14) 0.0129(15) -0.0048(14)
C1 0.053(2) 0.0587(18) 0.0529(16) -0.0044(14) 0.0192(15) -0.0046(14)
C2 0.069(3) 0.0586(19) 0.066(2) -0.0080(15) 0.0242(18) 0.0016(15)
C7 0.047(2) 0.068(2) 0.073(2) -0.0034(18) 0.0095(16) -0.0044(15)
C4 0.054(2) 0.072(2) 0.081(2) 0.0002(18) 0.0152(18) 0.0062(16)
C3 0.069(3) 0.069(2) 0.079(2) -0.0039(18) 0.0224(19) 0.0134(18)
C14 0.065(2) 0.0550(17) 0.0492(17) -0.0073(13) 0.0102(15) -0.0087(14)
C16 0.099(3) 0.056(2) 0.076(2) -0.0110(17) 0.024(2) -0.0068(18)
C17 0.148(4) 0.077(2) 0.0434(18) -0.0082(16) 0.013(2) -0.022(2)
C15 0.071(3) 0.120(4) 0.089(3) -0.047(3) -0.004(2) -0.012(2)
C18 0.056(2) 0.074(2) 0.0601(19) -0.0042(16) 0.0165(16) 0.0092(16)
C20 0.090(5) 0.57(2) 0.171(7) -0.174(10) -0.011(5) 0.136(8)
C19 0.217(9) 0.242(10) 0.56(2) -0.282(14) 0.269(13) -0.102(8)
C21 0.53(2) 0.379(15) 0.386(15) 0.289(14) 0.417(17) 0.349(16)
N1 0.0500(19) 0.0788(19) 0.0776(19) -0.0354(16) 0.0156(14) -0.0091(14)
N2 0.070(2) 0.085(2) 0.102(2) -0.024(2) 0.0065(18) -0.0091(17)
O1 0.0541(16) 0.0918(18) 0.0703(15) -0.0377(13) 0.0214(12) -0.0118(12)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C12 C13 1.385(4) . ?
C12 C11 1.397(4) . ?
C12 C14 1.541(4) . ?
C8 C9 1.381(4) . ?
C8 C13 1.390(4) . ?
C8 N1 1.401(4) . ?
C13 O1 1.392(4) . ?
C6 N1 1.378(4) . ?
C6 C5 1.389(5) . ?
C6 C1 1.401(4) . ?
C10 C9 1.376(4) . ?
C10 C11 1.391(4) . ?
C10 C18 1.538(4) . ?
C5 C4 1.401(5) . ?
C5 C7 1.435(5) . ?
C1 C2 1.364(4) . ?
C1 O1 1.374(4) . ?
C2 C3 1.391(5) . ?
C7 N2 1.141(4) . ?
C4 C3 1.368(5) . ?
C14 C16 1.524(5) . ?
C14 C15 1.524(5) . ?
C14 C17 1.528(5) . ?
C18 C21 1.391(8) . ?
C18 C20 1.407(7) . ?
C18 C19 1.445(8) . ?
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
C13 C12 C11 116.1(3) . . ?
C13 C12 C14 121.5(3) . . ?
C11 C12 C14 122.3(3) . . ?
C9 C8 C13 119.7(3) . . ?
C9 C8 N1 121.2(3) . . ?
C13 C8 N1 119.0(3) . . ?
C12 C13 C8 121.7(3) . . ?
C12 C13 O1 118.9(3) . . ?
C8 C13 O1 119.2(3) . . ?
N1 C6 C5 124.0(3) . . ?
N1 C6 C1 118.3(3) . . ?
C5 C6 C1 117.7(3) . . ?
C9 C10 C11 117.7(3) . . ?
C9 C10 C18 120.7(3) . . ?
C11 C10 C18 121.6(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C11 C12 123.7(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 C7 119.3(3) . . ?
C4 C5 C7 119.8(3) . . ?
C2 C1 O1 118.3(3) . . ?
C2 C1 C6 121.4(3) . . ?
O1 C1 C6 120.2(3) . . ?
C1 C2 C3 120.1(3) . . ?
N2 C7 C5 177.7(4) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C3 C2 120.1(3) . . ?
C16 C14 C15 107.2(3) . . ?
C16 C14 C17 109.5(3) . . ?
C15 C14 C17 108.6(3) . . ?
C16 C14 C12 111.3(3) . . ?
C15 C14 C12 111.3(3) . . ?
C17 C14 C12 108.9(3) . . ?
C21 C18 C20 110.2(8) . . ?
C21 C18 C19 107.4(9) . . ?
C20 C18 C19 104.4(8) . . ?
C21 C18 C10 110.2(4) . . ?
C20 C18 C10 112.6(4) . . ?
C19 C18 C10 111.9(4) . . ?
C6 N1 C8 119.7(3) . . ?
C1 O1 C13 118.4(2) . . ?
_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.053