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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_nitk98_0m_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O3'
_chemical_formula_weight         374.43

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   p21/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                   14.0952(13)
_cell_length_b                   10.0541(9)
_cell_length_c                   14.1685(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8180(10)
_cell_angle_gamma                90.00
_cell_volume                     1864.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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 APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14373
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3662
_reflns_number_gt                2950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0517P)^2^+0.4033P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3662
_refine_ls_number_parameters     299
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.051
_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
O001 O 0.01580(7) 0.13643(10) 0.12714(8) 0.0399(3) Uani 1 1 d U . .
O002 O 0.32215(7) 0.38062(9) 0.28469(8) 0.0370(3) Uani 1 1 d U . .
H002 H 0.3514 0.3110 0.2820 0.056 Uiso 1 1 calc R . .
O003 O 0.43601(7) 0.19259(11) 0.27057(7) 0.0405(3) Uani 1 1 d U . .
N004 N 0.01032(8) 0.36163(11) 0.13368(9) 0.0339(3) Uani 1 1 d U . .
N1 N 0.14092(10) 0.00266(14) 0.03041(10) 0.0425(3) Uani 1 1 d U . .
C006 C 0.17329(9) 0.24666(13) 0.20838(9) 0.0268(3) Uani 1 1 d U . .
C007 C 0.28924(9) 0.07827(13) 0.16669(9) 0.0282(3) Uani 1 1 d U . .
C008 C 0.22712(9) 0.11242(13) 0.23193(9) 0.0269(3) Uani 1 1 d U . .
H008 H 0.1709 0.0480 0.2101 0.032 Uiso 1 1 calc R . .
C009 C 0.06339(10) 0.24319(13) 0.15475(9) 0.0300(3) Uani 1 1 d U . .
C00A C 0.28303(9) 0.08175(13) 0.34555(9) 0.0291(3) Uani 1 1 d U . .
C00B C 0.16519(10) 0.48912(13) 0.20803(10) 0.0313(3) Uani 1 1 d U . .
C00C C 0.22182(9) 0.36621(13) 0.23432(9) 0.0287(3) Uani 1 1 d U . .
C00D C 0.39391(10) 0.11496(14) 0.19758(10) 0.0332(3) Uani 1 1 d U . .
C00E C 0.05875(10) 0.48432(14) 0.15694(10) 0.0330(3) Uani 1 1 d U . .
C00F C 0.24196(10) 0.01765(13) 0.07293(10) 0.0325(3) Uani 1 1 d U . .
C00G C 0.26522(11) 0.15405(15) 0.42034(10) 0.0376(3) Uani 1 1 d U . .
H00G H 0.2255 0.2307 0.4029 0.045 Uiso 1 1 calc R . .
C00H C 0.34460(11) -0.03133(15) 0.37507(11) 0.0401(3) Uani 1 1 d U . .
H00H H 0.3586 -0.0809 0.3264 0.048 Uiso 1 1 calc R . .
C00I C 0.21387(12) 0.61382(15) 0.22988(12) 0.0424(4) Uani 1 1 d U . .
H00I H 0.2844 0.6179 0.2636 0.051 Uiso 1 1 calc R . .
C00J C 0.00372(12) 0.60367(16) 0.12897(12) 0.0458(4) Uani 1 1 d U . .
H00J H -0.0668 0.6014 0.0950 0.055 Uiso 1 1 calc R . .
C00K C -0.10139(12) 0.3557(2) 0.08216(16) 0.0497(4) Uani 1 1 d U . .
C00L C 0.30222(13) -0.03297(19) 0.01217(12) 0.0462(4) Uani 1 1 d U . .
C00M C 0.45759(12) 0.0634(2) 0.14051(14) 0.0492(4) Uani 1 1 d U . .
C00N C 0.30605(14) 0.11347(19) 0.52146(12) 0.0513(4) Uani 1 1 d U . .
H00N H 0.2930 0.1630 0.5708 0.062 Uiso 1 1 calc R . .
C00O C 0.15901(14) 0.72887(16) 0.20220(13) 0.0533(4) Uani 1 1 d U . .
H00O H 0.1921 0.8106 0.2172 0.064 Uiso 1 1 calc R . .
C00P C 0.41237(13) -0.05903(19) 0.07793(14) 0.0515(4) Uani 1 1 d U . .
C00Q C 0.05351(14) 0.72351(17) 0.15154(14) 0.0542(4) Uani 1 1 d U . .
H00Q H 0.0164 0.8021 0.1328 0.065 Uiso 1 1 calc R . .
C00R C 0.38508(12) -0.07054(19) 0.47590(12) 0.0526(4) Uani 1 1 d U . .
H00R H 0.4260 -0.1460 0.4943 0.063 Uiso 1 1 calc R . .
C00S C 0.36515(13) 0.0014(2) 0.54915(12) 0.0571(5) Uani 1 1 d U . .
H00S H 0.3916 -0.0258 0.6167 0.068 Uiso 1 1 calc R . .
H1 H 0.0993(13) 0.0393(18) 0.0622(13) 0.052(5) Uiso 1 1 d . . .
H2 H 0.1135(14) -0.0452(19) -0.0258(15) 0.058(5) Uiso 1 1 d . . .
H3 H 0.2677(14) -0.110(2) -0.0235(14) 0.058(5) Uiso 1 1 d . . .
H4 H 0.3020(15) 0.036(2) -0.0401(16) 0.078(6) Uiso 1 1 d . . .
H5 H 0.4531(14) -0.0812(19) 0.0333(14) 0.064(5) Uiso 1 1 d . . .
H6 H 0.4161(15) -0.135(2) 0.1272(15) 0.067(6) Uiso 1 1 d . . .
H7 H 0.4616(16) 0.137(2) 0.0943(17) 0.080(7) Uiso 1 1 d . . .
H8 H 0.5274(16) 0.0498(19) 0.1874(15) 0.065(5) Uiso 1 1 d . . .
H9 H -0.1298(16) 0.413(2) 0.1208(16) 0.078(6) Uiso 1 1 d . . .
H10 H -0.1205(19) 0.381(2) 0.014(2) 0.097(8) Uiso 1 1 d . . .
H11 H -0.1218(17) 0.271(2) 0.0960(17) 0.088(7) 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
O001 0.0260(5) 0.0374(6) 0.0486(6) -0.0102(4) 0.0048(4) -0.0043(4)
O002 0.0267(5) 0.0322(5) 0.0452(6) -0.0037(4) 0.0054(4) -0.0033(4)
O003 0.0281(5) 0.0458(6) 0.0427(6) -0.0095(5) 0.0073(4) -0.0037(4)
N004 0.0247(6) 0.0372(7) 0.0370(6) -0.0017(5) 0.0081(5) 0.0043(5)
N1 0.0361(7) 0.0499(8) 0.0328(6) -0.0153(6) 0.0027(5) -0.0010(6)
C006 0.0248(6) 0.0298(7) 0.0242(6) -0.0009(5) 0.0072(5) 0.0007(5)
C007 0.0281(6) 0.0274(7) 0.0263(6) 0.0010(5) 0.0069(5) 0.0033(5)
C008 0.0240(6) 0.0268(6) 0.0266(6) -0.0021(5) 0.0057(5) -0.0028(5)
C009 0.0273(6) 0.0336(7) 0.0278(6) -0.0042(5) 0.0087(5) 0.0003(5)
C00A 0.0240(6) 0.0332(7) 0.0275(6) 0.0004(5) 0.0064(5) -0.0065(5)
C00B 0.0345(7) 0.0298(7) 0.0299(6) -0.0004(5) 0.0121(5) 0.0010(5)
C00C 0.0270(6) 0.0327(7) 0.0254(6) -0.0014(5) 0.0087(5) -0.0007(5)
C00D 0.0293(7) 0.0355(7) 0.0324(7) 0.0027(6) 0.0088(5) 0.0045(6)
C00E 0.0360(7) 0.0324(7) 0.0318(7) 0.0011(6) 0.0139(6) 0.0047(6)
C00F 0.0359(7) 0.0299(7) 0.0290(6) 0.0006(5) 0.0089(6) 0.0030(6)
C00G 0.0414(8) 0.0389(8) 0.0330(7) -0.0034(6) 0.0143(6) -0.0077(6)
C00H 0.0355(7) 0.0435(8) 0.0379(7) 0.0057(6) 0.0096(6) 0.0026(6)
C00I 0.0444(8) 0.0341(8) 0.0442(8) -0.0013(6) 0.0112(7) -0.0030(6)
C00J 0.0408(8) 0.0449(9) 0.0509(9) 0.0044(7) 0.0160(7) 0.0121(7)
C00K 0.0256(7) 0.0517(11) 0.0643(12) -0.0026(9) 0.0079(7) 0.0055(7)
C00L 0.0527(9) 0.0505(10) 0.0365(8) -0.0110(8) 0.0178(7) 0.0019(8)
C00M 0.0350(8) 0.0639(11) 0.0515(9) -0.0082(9) 0.0193(7) 0.0036(8)
C00N 0.0599(10) 0.0632(11) 0.0305(7) -0.0060(7) 0.0164(7) -0.0172(9)
C00O 0.0643(11) 0.0285(8) 0.0634(11) 0.0008(7) 0.0194(9) -0.0011(7)
C00P 0.0527(10) 0.0535(11) 0.0550(10) -0.0072(8) 0.0277(8) 0.0111(8)
C00Q 0.0628(11) 0.0330(8) 0.0675(11) 0.0075(8) 0.0248(9) 0.0141(8)
C00R 0.0403(8) 0.0599(11) 0.0493(9) 0.0217(8) 0.0069(7) 0.0054(8)
C00S 0.0509(10) 0.0810(14) 0.0295(7) 0.0150(8) 0.0035(7) -0.0106(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
O001 C009 1.2490(16) . ?
O002 C00C 1.3341(15) . ?
O003 C00D 1.2548(16) . ?
N004 C009 1.3787(17) . ?
N004 C00E 1.3889(18) . ?
N004 C00K 1.4701(18) . ?
N1 C00F 1.3327(18) . ?
C006 C00C 1.3642(18) . ?
C006 C009 1.4503(17) . ?
C006 C008 1.5233(17) . ?
C007 C00F 1.3864(18) . ?
C007 C00D 1.4229(18) . ?
C007 C008 1.5299(18) . ?
C008 C00A 1.5378(17) . ?
C00A C00G 1.3828(19) . ?
C00A C00H 1.397(2) . ?
C00B C00E 1.4035(19) . ?
C00B C00I 1.407(2) . ?
C00B C00C 1.4428(18) . ?
C00D C00M 1.506(2) . ?
C00E C00J 1.404(2) . ?
C00F C00L 1.505(2) . ?
C00G C00N 1.392(2) . ?
C00H C00R 1.384(2) . ?
C00I C00O 1.365(2) . ?
C00J C00Q 1.371(2) . ?
C00L C00P 1.507(2) . ?
C00M C00P 1.512(3) . ?
C00N C00S 1.369(3) . ?
C00O C00Q 1.391(3) . ?
C00R C00S 1.377(3) . ?

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
C009 N004 C00E 122.44(11) . . ?
C009 N004 C00K 117.87(12) . . ?
C00E N004 C00K 119.66(12) . . ?
C00C C006 C009 119.56(11) . . ?
C00C C006 C008 124.24(11) . . ?
C009 C006 C008 116.20(11) . . ?
C00F C007 C00D 118.87(12) . . ?
C00F C007 C008 119.89(11) . . ?
C00D C007 C008 121.12(11) . . ?
C006 C008 C007 114.63(10) . . ?
C006 C008 C00A 115.26(10) . . ?
C007 C008 C00A 113.69(10) . . ?
O001 C009 N004 119.30(11) . . ?
O001 C009 C006 121.97(12) . . ?
N004 C009 C006 118.73(11) . . ?
C00G C00A C00H 117.91(12) . . ?
C00G C00A C008 121.90(12) . . ?
C00H C00A C008 119.76(12) . . ?
C00E C00B C00I 118.97(13) . . ?
C00E C00B C00C 119.11(12) . . ?
C00I C00B C00C 121.90(12) . . ?
O002 C00C C006 124.43(12) . . ?
O002 C00C C00B 114.83(11) . . ?
C006 C00C C00B 120.74(11) . . ?
O003 C00D C007 122.24(12) . . ?
O003 C00D C00M 117.58(13) . . ?
C007 C00D C00M 120.16(13) . . ?
N004 C00E C00J 121.40(13) . . ?
N004 C00E C00B 119.33(12) . . ?
C00J C00E C00B 119.27(13) . . ?
N1 C00F C007 122.36(13) . . ?
N1 C00F C00L 116.02(13) . . ?
C007 C00F C00L 121.62(13) . . ?
C00A C00G C00N 120.75(15) . . ?
C00R C00H C00A 120.85(15) . . ?
C00O C00I C00B 120.92(15) . . ?
C00Q C00J C00E 120.28(15) . . ?
C00F C00L C00P 112.08(13) . . ?
C00D C00M C00P 112.93(14) . . ?
C00S C00N C00G 120.73(16) . . ?
C00I C00O C00Q 119.87(15) . . ?
C00L C00P C00M 109.50(14) . . ?
C00J C00Q C00O 120.70(15) . . ?
C00S C00R C00H 120.46(16) . . ?
C00N C00S C00R 119.29(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 938662'