# 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_123

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2 O2'
_chemical_formula_weight         382.45

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1346(2)
_cell_length_b                   15.0120(4)
_cell_length_c                   26.4598(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2039.54(11)
_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            Red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.2454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12770
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.48
_reflns_number_total             2471
_reflns_number_gt                1546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_number_reflns         2471
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   0.747
_refine_ls_restrained_S_all      0.747
_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
C6 C 0.1163(6) 0.46178(19) 0.92578(10) 0.0591(8) Uani 1 1 d . . .
C1 C -0.0767(7) 0.39897(18) 0.91734(11) 0.0585(8) Uani 1 1 d . . .
C18 C 0.3872(6) 0.54435(17) 0.64375(11) 0.0547(8) Uani 1 1 d . . .
C2 C -0.1814(6) 0.38881(17) 0.86994(12) 0.0637(8) Uani 1 1 d . . .
H2 H -0.3128 0.3471 0.8649 0.076 Uiso 1 1 calc R . .
C19 C 0.5264(7) 0.55785(18) 0.59933(11) 0.0644(8) Uani 1 1 d . . .
H19 H 0.4910 0.5230 0.5711 0.077 Uiso 1 1 calc R . .
C23 C 0.4444(7) 0.5984(2) 0.68501(11) 0.0751(9) Uani 1 1 d . . .
H23 H 0.3531 0.5908 0.7151 0.090 Uiso 1 1 calc R . .
C10 C -0.3361(6) 0.31319(16) 0.62560(10) 0.0541(7) Uani 1 1 d . . .
C8 C -0.0900(7) 0.34277(17) 0.75280(10) 0.0721(9) Uani 1 1 d . . .
H8A H 0.0932 0.3541 0.7466 0.086 Uiso 1 1 calc R . .
H8B H -0.1024 0.2928 0.7759 0.086 Uiso 1 1 calc R . .
C12 C -0.6838(7) 0.20114(19) 0.63506(13) 0.0744(9) Uani 1 1 d . . .
H12 H -0.7808 0.1623 0.6550 0.089 Uiso 1 1 calc R . .
C5 C 0.2066(7) 0.51275(17) 0.88574(12) 0.0696(9) Uani 1 1 d . . .
H5 H 0.3384 0.5543 0.8907 0.084 Uiso 1 1 calc R . .
C20 C 0.7164(7) 0.6225(2) 0.59680(11) 0.0714(9) Uani 1 1 d . . .
H20 H 0.8091 0.6309 0.5670 0.086 Uiso 1 1 calc R . .
C7 C -0.2103(7) 0.42416(19) 0.77739(10) 0.0787(10) Uani 1 1 d . . .
H7A H -0.1799 0.4760 0.7563 0.094 Uiso 1 1 calc R . .
H7B H -0.3969 0.4158 0.7804 0.094 Uiso 1 1 calc R . .
C17 C 0.1935(7) 0.4767(2) 0.64759(10) 0.0633(9) Uani 1 1 d . . .
C9 C -0.1630(6) 0.35441(17) 0.65921(10) 0.0539(7) Uani 1 1 d . . .
C4 C 0.0981(8) 0.5011(2) 0.83803(12) 0.0742(10) Uani 1 1 d . . .
H4 H 0.1581 0.5360 0.8114 0.089 Uiso 1 1 calc R . .
C16 C 0.0298(7) 0.4195(2) 0.65212(10) 0.0603(9) Uani 1 1 d . . .
C22 C 0.6315(8) 0.6621(2) 0.68198(12) 0.0833(10) Uani 1 1 d . . .
H22 H 0.6667 0.6976 0.7099 0.100 Uiso 1 1 calc R . .
C21 C 0.7689(7) 0.67450(19) 0.63820(13) 0.0790(10) Uani 1 1 d . . .
H21 H 0.8974 0.7181 0.6365 0.095 Uiso 1 1 calc R . .
C11 C -0.4859(6) 0.25383(18) 0.65591(11) 0.0599(8) Uani 1 1 d . . .
C15 C -0.3902(7) 0.31868(19) 0.57324(10) 0.0645(8) Uani 1 1 d . . .
H15 H -0.2966 0.3572 0.5525 0.077 Uiso 1 1 calc R . .
C13 C -0.7286(7) 0.20895(19) 0.58455(14) 0.0774(9) Uani 1 1 d . . .
H13 H -0.8602 0.1753 0.5698 0.093 Uiso 1 1 calc R . .
C3 C -0.0948(7) 0.4398(2) 0.82905(10) 0.0666(9) Uani 1 1 d . . .
C14 C -0.5804(8) 0.2669(2) 0.55408(11) 0.0737(9) Uani 1 1 d . . .
H14 H -0.6149 0.2694 0.5196 0.088 Uiso 1 1 calc R . .
C25 C -0.3412(7) 0.2840(2) 0.95215(11) 0.0864(10) Uani 1 1 d . . .
H25A H -0.5008 0.3110 0.9411 0.130 Uiso 1 1 calc R . .
H25B H -0.3702 0.2530 0.9834 0.130 Uiso 1 1 calc R . .
H25C H -0.2820 0.2426 0.9270 0.130 Uiso 1 1 calc R . .
C24 C 0.4094(8) 0.5296(2) 0.98493(11) 0.0884(11) Uani 1 1 d . . .
H24A H 0.5654 0.5112 0.9679 0.133 Uiso 1 1 calc R . .
H24B H 0.4403 0.5315 1.0207 0.133 Uiso 1 1 calc R . .
H24C H 0.3594 0.5877 0.9733 0.133 Uiso 1 1 calc R . .
N2 N -0.4070(6) 0.25776(16) 0.70511(9) 0.0717(7) Uani 1 1 d . . .
N1 N -0.2150(5) 0.31880(15) 0.70523(9) 0.0627(7) Uani 1 1 d . . .
O2 O -0.1496(5) 0.35096(13) 0.95943(7) 0.0790(6) Uani 1 1 d . . .
O1 O 0.2069(5) 0.46808(14) 0.97448(8) 0.0823(7) Uani 1 1 d . . .


_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
C6 O1 1.373(3) . ?
C6 C1 1.386(4) . ?
C6 C5 1.387(4) . ?
C1 C2 1.373(4) . ?
C1 O2 1.378(3) . ?
C18 C19 1.390(4) . ?
C18 C23 1.391(4) . ?
C18 C17 1.425(5) . ?
C2 C3 1.398(4) . ?
C19 C20 1.377(4) . ?
C23 C22 1.358(4) . ?
C10 C9 1.401(4) . ?
C10 C15 1.415(4) . ?
C10 C11 1.424(4) . ?
C8 N1 1.458(3) . ?
C8 C7 1.516(4) . ?
C12 C13 1.361(4) . ?
C12 C11 1.401(4) . ?
C5 C4 1.391(4) . ?
C20 C21 1.372(4) . ?
C7 C3 1.508(4) . ?
C17 C16 1.207(5) . ?
C9 N1 1.356(3) . ?
C9 C16 1.404(4) . ?
C4 C3 1.373(4) . ?
C22 C21 1.369(4) . ?
C11 N2 1.364(3) . ?
C15 C14 1.348(4) . ?
C13 C14 1.409(4) . ?
C25 O2 1.420(4) . ?
C24 O1 1.418(4) . ?
N2 N1 1.346(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
O1 C6 C1 116.1(3) . . ?
O1 C6 C5 124.4(3) . . ?
C1 C6 C5 119.4(3) . . ?
C2 C1 O2 125.0(3) . . ?
C2 C1 C6 120.2(3) . . ?
O2 C1 C6 114.8(3) . . ?
C19 C18 C23 118.0(3) . . ?
C19 C18 C17 121.5(3) . . ?
C23 C18 C17 120.4(3) . . ?
C1 C2 C3 121.4(3) . . ?
C20 C19 C18 120.5(3) . . ?
C22 C23 C18 120.9(3) . . ?
C9 C10 C15 136.0(3) . . ?
C9 C10 C11 105.2(2) . . ?
C15 C10 C11 118.8(3) . . ?
N1 C8 C7 113.0(2) . . ?
C13 C12 C11 117.4(3) . . ?
C6 C5 C4 119.4(3) . . ?
C21 C20 C19 120.1(3) . . ?
C3 C7 C8 110.8(3) . . ?
C16 C17 C18 178.4(3) . . ?
N1 C9 C10 105.7(2) . . ?
N1 C9 C16 122.2(3) . . ?
C10 C9 C16 132.1(3) . . ?
C3 C4 C5 122.0(3) . . ?
C17 C16 C9 177.8(3) . . ?
C23 C22 C21 120.7(3) . . ?
C22 C21 C20 119.8(3) . . ?
N2 C11 C12 128.0(3) . . ?
N2 C11 C10 110.5(3) . . ?
C12 C11 C10 121.5(3) . . ?
C14 C15 C10 118.5(3) . . ?
C12 C13 C14 121.6(3) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 C7 123.0(3) . . ?
C2 C3 C7 119.4(3) . . ?
C15 C14 C13 122.2(3) . . ?
N1 N2 C11 104.4(2) . . ?
N2 N1 C9 114.2(2) . . ?
N2 N1 C8 119.5(2) . . ?
C9 N1 C8 126.2(3) . . ?
C1 O2 C25 116.7(2) . . ?
C6 O1 C24 118.4(2) . . ?

_diffrn_measured_fraction_theta_max 100.00
_diffrn_reflns_theta_full        26.48
_diffrn_measured_fraction_theta_full 100.00
_refine_diff_density_max         0.083
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 1008821'
