# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_xa037

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 N2 O3'
_chemical_formula_weight         390.47

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                   9.2790(17)
_cell_length_b                   17.285(3)
_cell_length_c                   13.653(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.450(3)
_cell_angle_gamma                90.00
_cell_volume                     2100.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    188(2)
_cell_measurement_reflns_used    753
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      17.44

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      188(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 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            12189
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.1145
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3709
_reflns_number_gt                1854
_reflns_threshold_expression     >2sigma(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, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1203P)²+1.0247P] where P=(Fo²+2Fc²)/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         3709
_refine_ls_number_parameters     274
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1870
_refine_ls_R_factor_gt           0.0981
_refine_ls_wR_factor_ref         0.2775
_refine_ls_wR_factor_gt          0.2287
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_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 0.8799(4) 0.04274(19) 0.6097(2) 0.0448(9) Uani 1 1 d . . .
O2 O 0.4016(4) -0.2187(2) 0.9751(3) 0.0629(12) Uani 1 1 d . . .
O3 O 0.4422(5) -0.3434(2) 0.9010(3) 0.0646(12) Uani 1 1 d . . .
H3 H 0.4302 -0.3119 0.9450 0.097 Uiso 1 1 calc R . .
N1 N 1.0352(5) -0.0521(3) 0.6760(3) 0.0527(12) Uani 1 1 d . . .
N2 N 1.1177(5) 0.0076(3) 0.6461(3) 0.0525(12) Uani 1 1 d . . .
C1 C 0.8986(7) -0.0294(3) 0.6537(4) 0.0453(14) Uani 1 1 d . . .
C2 C 1.0223(6) 0.0622(3) 0.6084(4) 0.0443(13) Uani 1 1 d . . .
C3 C 1.0479(6) 0.1372(3) 0.5693(4) 0.0453(13) Uani 1 1 d . . .
C4 C 1.1810(6) 0.1543(3) 0.5495(4) 0.0459(14) Uani 1 1 d . . .
H4 H 1.2597 0.1172 0.5636 0.055 Uiso 1 1 calc R . .
C5 C 1.2013(6) 0.2256(3) 0.5088(4) 0.0486(14) Uani 1 1 d . . .
H5 H 1.2946 0.2365 0.4959 0.058 Uiso 1 1 calc R . .
C6 C 1.0894(6) 0.2815(3) 0.4865(4) 0.0478(14) Uani 1 1 d . A .
C7 C 0.9573(7) 0.2640(4) 0.5074(5) 0.0624(17) Uani 1 1 d . . .
H7 H 0.8790 0.3014 0.4936 0.075 Uiso 1 1 calc R . .
C8 C 0.9352(7) 0.1935(4) 0.5482(4) 0.0607(17) Uani 1 1 d . . .
H8 H 0.8424 0.1831 0.5620 0.073 Uiso 1 1 calc R . .
C9 C 1.1126(6) 0.3602(3) 0.4391(4) 0.0543(15) Uani 1 1 d D . .
C10 C 1.2105(13) 0.4118(8) 0.5240(8) 0.079(3) Uani 0.50 1 d PD A 1
H10A H 1.2236 0.4625 0.4957 0.118 Uiso 0.50 1 calc PR A 1
H10B H 1.3090 0.3874 0.5522 0.118 Uiso 0.50 1 calc PR A 1
H10C H 1.1614 0.4182 0.5783 0.118 Uiso 0.50 1 calc PR A 1
C11 C 1.1959(14) 0.3497(9) 0.3576(9) 0.079(3) Uani 0.50 1 d PD A 1
H11A H 1.2181 0.4005 0.3335 0.118 Uiso 0.50 1 calc PR A 1
H11B H 1.1328 0.3201 0.3001 0.118 Uiso 0.50 1 calc PR A 1
H11C H 1.2900 0.3217 0.3871 0.118 Uiso 0.50 1 calc PR A 1
C12 C 0.9658(11) 0.4034(8) 0.3893(9) 0.079(3) Uani 0.50 1 d PD A 1
H12A H 0.9288 0.4277 0.4424 0.118 Uiso 0.50 1 calc PR A 1
H12B H 0.8906 0.3669 0.3502 0.118 Uiso 0.50 1 calc PR A 1
H12C H 0.9842 0.4434 0.3433 0.118 Uiso 0.50 1 calc PR A 1
C10' C 1.1410(15) 0.4226(7) 0.5212(8) 0.081(3) Uani 0.50 1 d PD A 2
H10D H 1.1743 0.4701 0.4952 0.122 Uiso 0.50 1 calc PR A 2
H10E H 1.2189 0.4050 0.5818 0.122 Uiso 0.50 1 calc PR A 2
H10F H 1.0479 0.4328 0.5395 0.122 Uiso 0.50 1 calc PR A 2
C11' C 1.2476(11) 0.3617(10) 0.3930(10) 0.081(3) Uani 0.50 1 d PD A 2
H11D H 1.2488 0.4111 0.3581 0.122 Uiso 0.50 1 calc PR A 2
H11E H 1.2378 0.3192 0.3441 0.122 Uiso 0.50 1 calc PR A 2
H11F H 1.3415 0.3558 0.4479 0.122 Uiso 0.50 1 calc PR A 2
C12' C 0.9726(10) 0.3795(9) 0.3529(8) 0.081(3) Uani 0.50 1 d PD A 2
H12D H 0.8859 0.3832 0.3802 0.122 Uiso 0.50 1 calc PR A 2
H12E H 0.9548 0.3387 0.3010 0.122 Uiso 0.50 1 calc PR A 2
H12F H 0.9871 0.4290 0.3221 0.122 Uiso 0.50 1 calc PR A 2
C13 C 0.7653(6) -0.0680(3) 0.6667(4) 0.0427(13) Uani 1 1 d . . .
C14 C 0.6229(6) -0.0362(3) 0.6294(4) 0.0489(14) Uani 1 1 d . . .
H14 H 0.6110 0.0123 0.5953 0.059 Uiso 1 1 calc R . .
C15 C 0.4978(6) -0.0747(3) 0.6416(4) 0.0513(15) Uani 1 1 d . . .
H15 H 0.4010 -0.0522 0.6153 0.062 Uiso 1 1 calc R . .
C16 C 0.5119(6) -0.1454(3) 0.6917(4) 0.0443(13) Uani 1 1 d . . .
C17 C 0.6546(7) -0.1755(3) 0.7294(4) 0.0520(15) Uani 1 1 d . . .
H17 H 0.6672 -0.2233 0.7653 0.062 Uiso 1 1 calc R . .
C18 C 0.7793(7) -0.1384(3) 0.7165(4) 0.0532(15) Uani 1 1 d . . .
H18 H 0.8757 -0.1614 0.7420 0.064 Uiso 1 1 calc R . .
C19 C 0.3746(6) -0.1870(3) 0.7015(4) 0.0523(15) Uani 1 1 d . . .
H19A H 0.3437 -0.2252 0.6454 0.063 Uiso 1 1 calc R . .
H19B H 0.2920 -0.1489 0.6923 0.063 Uiso 1 1 calc R . .
C20 C 0.3934(6) -0.2294(3) 0.8036(4) 0.0516(14) Uani 1 1 d . . .
C21 C 0.3832(6) -0.1866(4) 0.8892(5) 0.0559(15) Uani 1 1 d . . .
C22 C 0.3491(7) -0.1014(3) 0.8823(5) 0.0712(19) Uani 1 1 d . . .
H22A H 0.3630 -0.0805 0.9511 0.107 Uiso 1 1 calc R . .
H22B H 0.2449 -0.0933 0.8414 0.107 Uiso 1 1 calc R . .
H22C H 0.4171 -0.0750 0.8500 0.107 Uiso 1 1 calc R . .
C23 C 0.4261(6) -0.3067(4) 0.8130(4) 0.0551(15) Uani 1 1 d . . .
C24 C 0.4495(7) -0.3613(3) 0.7318(5) 0.0700(18) Uani 1 1 d . . .
H24A H 0.5519 -0.3820 0.7536 0.105 Uiso 1 1 calc R . .
H24B H 0.4344 -0.3331 0.6674 0.105 Uiso 1 1 calc R . .
H24C H 0.3773 -0.4040 0.7221 0.105 Uiso 1 1 calc R . .


_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 C2 1.369(6) . ?
O1 C1 1.374(6) . ?
O2 C21 1.264(6) . ?
O3 C23 1.329(6) . ?
O3 H3 0.8400 . ?
N1 C1 1.278(6) . ?
N1 N2 1.411(6) . ?
N2 C2 1.297(6) . ?
C1 C13 1.460(7) . ?
C2 C3 1.446(7) . ?
C3 C4 1.370(7) . ?
C3 C8 1.397(7) . ?
C4 C5 1.385(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(7) . ?
C6 C9 1.547(7) . ?
C7 C8 1.380(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10' 1.523(8) . ?
C9 C12 1.534(8) . ?
C9 C12' 1.522(8) . ?
C9 C11' 1.553(8) . ?
C9 C10 1.538(8) . ?
C9 C11 1.535(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13 C14 1.388(7) . ?
C13 C18 1.382(7) . ?
C14 C15 1.389(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(7) . ?
C16 C19 1.501(7) . ?
C17 C18 1.378(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.540(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C23 1.368(7) . ?
C20 C21 1.410(7) . ?
C21 C22 1.503(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.517(8) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C2 O1 C1 103.0(4) . . ?
C23 O3 H3 109.5 . . ?
C1 N1 N2 106.8(4) . . ?
C2 N2 N1 106.4(4) . . ?
N1 C1 O1 112.1(5) . . ?
N1 C1 C13 130.4(5) . . ?
O1 C1 C13 117.5(5) . . ?
N2 C2 O1 111.6(5) . . ?
N2 C2 C3 129.3(5) . . ?
O1 C2 C3 119.0(5) . . ?
C4 C3 C8 118.2(5) . . ?
C4 C3 C2 121.2(5) . . ?
C8 C3 C2 120.6(5) . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.3(5) . . ?
C7 C6 C9 121.4(5) . . ?
C5 C6 C9 121.3(5) . . ?
C6 C7 C8 121.6(5) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 120.7(5) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C10' C9 C6 109.3(7) . . ?
C12 C9 C6 113.7(7) . . ?
C10' C9 C12' 110.2(6) . . ?
C6 C9 C12' 109.0(7) . . ?
C10' C9 C11' 107.2(6) . . ?
C6 C9 C11' 114.1(7) . . ?
C12' C9 C11' 107.0(6) . . ?
C12 C9 C10 108.3(6) . . ?
C6 C9 C10 108.5(7) . . ?
C12 C9 C11 107.6(6) . . ?
C6 C9 C11 110.9(7) . . ?
C10 C9 C11 107.7(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
C9 C10' H10D 109.5 . . ?
C9 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C9 C11' H11D 109.5 . . ?
C9 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C9 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C9 C12' H12D 109.5 . . ?
C9 C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C9 C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C14 C13 C18 118.4(5) . . ?
C14 C13 C1 121.7(5) . . ?
C18 C13 C1 119.8(5) . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 117.5(5) . . ?
C17 C16 C19 122.4(5) . . ?
C15 C16 C19 120.1(5) . . ?
C16 C17 C18 121.9(5) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C13 120.5(5) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C16 C19 C20 115.3(5) . . ?
C16 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C16 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C23 C20 C21 120.0(5) . . ?
C23 C20 C19 121.0(5) . . ?
C21 C20 C19 118.9(5) . . ?
O2 C21 C20 121.0(6) . . ?
O2 C21 C22 117.3(5) . . ?
C20 C21 C22 121.6(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C20 121.1(5) . . ?
O3 C23 C24 111.2(5) . . ?
C20 C23 C24 127.7(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 944929'
