# 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:
#                         www.ccdc.cam.ac.uk
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#  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_x

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         304.38
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   4.8043(4)
_cell_length_b                   14.2030(11)
_cell_length_c                   23.1328(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.576(8)
_cell_angle_gamma                90
_cell_volume                     1577.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    16392
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      25.0
_cell_special_details            
;
;
_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9842


#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      120(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_reflns_number            16392
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             2779
# number of observed reflections (> n sig(I))
_reflns_number_gt                2212
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
#===============================================================================

# 8. REFINEMENT DATA
_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 > 2σ(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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2779
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1913
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_restrained_S_all      1.284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.053

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
O O 0.6710(4) 0.01943(13) 0.28625(8) 0.0325(5) Uani 1 1 d . . .
N2 N 0.2895(4) 0.30966(15) 0.13016(9) 0.0250(6) Uani 1 1 d . . .
N3 N 0.4908(4) 0.25698(15) 0.10454(9) 0.0261(6) Uani 1 1 d . . .
C4 C 0.7624(5) 0.11464(18) 0.13951(11) 0.0242(6) Uani 1 1 d . . .
C5 C 0.4160(5) 0.20263(18) 0.19382(10) 0.0216(6) Uani 1 1 d . . .
C6 C 0.7913(5) 0.05588(17) 0.18927(11) 0.0240(6) Uani 1 1 d . . .
C7 C 0.0605(5) 0.30571(18) 0.22927(11) 0.0254(6) Uani 1 1 d . . .
H7 H -0.0614 0.3562 0.2250 0.030 Uiso 1 1 calc R . .
C8 C 0.4910(5) 0.63700(18) 0.06304(11) 0.0248(6) Uani 1 1 d . . .
H8B H 0.5831 0.6440 0.1006 0.030 Uiso 1 1 calc R . .
H8A H 0.6313 0.6193 0.0357 0.030 Uiso 1 1 calc R . .
C9 C 0.4312(5) 0.14915(18) 0.24432(11) 0.0234(6) Uani 1 1 d . . .
C10 C 0.5648(5) 0.19145(18) 0.14321(10) 0.0217(6) Uani 1 1 d . . .
C11 C 0.9175(5) 0.09539(19) 0.09095(11) 0.0278(7) Uani 1 1 d . . .
H11 H 0.8980 0.1335 0.0584 0.033 Uiso 1 1 calc R . .
C12 C 0.2778(5) 0.55806(18) 0.06628(10) 0.0241(6) Uani 1 1 d . . .
H12A H 0.1217 0.5797 0.0884 0.029 Uiso 1 1 calc R . .
H12B H 0.2085 0.5436 0.0275 0.029 Uiso 1 1 calc R . .
C13 C 0.2393(5) 0.27920(18) 0.18545(11) 0.0230(6) Uani 1 1 d . . .
C14 C 0.3673(5) 0.73135(19) 0.04496(12) 0.0284(7) Uani 1 1 d . . .
H14A H 0.2295 0.7497 0.0727 0.034 Uiso 1 1 calc R . .
H14B H 0.2728 0.7243 0.0076 0.034 Uiso 1 1 calc R . .
C15 C 0.0755(5) 0.25233(19) 0.27944(12) 0.0280(7) Uani 1 1 d . . .
H15 H -0.0413 0.2682 0.3093 0.034 Uiso 1 1 calc R . .
C16 C 0.6346(5) 0.07057(18) 0.24411(11) 0.0249(6) Uani 1 1 d . . .
C17 C 0.3947(5) 0.46865(18) 0.09382(11) 0.0251(6) Uani 1 1 d . . .
H17B H 0.5425 0.4447 0.0702 0.030 Uiso 1 1 calc R . .
H17A H 0.4756 0.4839 0.1315 0.030 Uiso 1 1 calc R . .
C18 C 0.9783(5) -0.01911(19) 0.18746(12) 0.0292(7) Uani 1 1 d . . .
H18 H 1.0007 -0.0578 0.2197 0.035 Uiso 1 1 calc R . .
C19 C 1.0989(6) 0.02069(19) 0.09069(12) 0.0321(7) Uani 1 1 d . . .
H19 H 1.2015 0.0086 0.0580 0.038 Uiso 1 1 calc R . .
C20 C 0.1784(5) 0.39211(18) 0.10081(11) 0.0253(6) Uani 1 1 d . . .
H20A H 0.0251 0.4170 0.1226 0.030 Uiso 1 1 calc R . .
H20B H 0.1056 0.3738 0.0629 0.030 Uiso 1 1 calc R . .
C21 C 1.1304(6) -0.0372(2) 0.13911(12) 0.0328(7) Uani 1 1 d . . .
H21 H 1.2535 -0.0877 0.1388 0.039 Uiso 1 1 calc R . .
C22 C 0.2569(5) 0.17565(19) 0.28778(11) 0.0271(7) Uani 1 1 d . . .
H22 H 0.2594 0.1428 0.3226 0.033 Uiso 1 1 calc R . .
C23 C 0.5833(6) 0.8091(2) 0.04095(12) 0.0346(7) Uani 1 1 d . . .
H23A H 0.7175 0.7923 0.0127 0.052 Uiso 1 1 calc R . .
H23C H 0.6757 0.8173 0.0779 0.052 Uiso 1 1 calc R . .
H23B H 0.4932 0.8668 0.0297 0.052 Uiso 1 1 calc R . .


_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
O C16 1.224(3) . ?
N2 N3 1.370(3) . ?
N2 C13 1.378(3) . ?
N2 C20 1.448(3) . ?
N3 C10 1.332(3) . ?
C4 C11 1.392(4) . ?
C4 C6 1.425(4) . ?
C4 C10 1.450(4) . ?
C5 C13 1.390(4) . ?
C5 C9 1.394(3) . ?
C5 C10 1.398(3) . ?
C6 C18 1.395(4) . ?
C6 C16 1.508(4) . ?
C7 C15 1.387(4) . ?
C7 C13 1.398(4) . ?
C8 C14 1.520(4) . ?
C8 C12 1.522(4) . ?
C9 C22 1.378(4) . ?
C9 C16 1.484(4) . ?
C11 C19 1.373(4) . ?
C12 C17 1.521(3) . ?
C14 C23 1.520(4) . ?
C15 C22 1.405(4) . ?
C17 C20 1.516(3) . ?
C18 C21 1.377(4) . ?
C19 C21 1.394(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
N3 N2 C13 111.9(2) . . ?
N3 N2 C20 119.6(2) . . ?
C13 N2 C20 128.1(2) . . ?
C10 N3 N2 105.6(2) . . ?
C11 C4 C6 119.6(2) . . ?
C11 C4 C10 124.1(2) . . ?
C6 C4 C10 116.3(2) . . ?
C13 C5 C9 124.1(2) . . ?
C13 C5 C10 107.3(2) . . ?
C9 C5 C10 128.6(2) . . ?
C18 C6 C4 118.1(2) . . ?
C18 C6 C16 117.9(2) . . ?
C4 C6 C16 124.0(2) . . ?
C15 C7 C13 116.2(2) . . ?
C14 C8 C12 113.9(2) . . ?
C22 C9 C5 116.3(2) . . ?
C22 C9 C16 128.4(2) . . ?
C5 C9 C16 115.3(2) . . ?
N3 C10 C5 110.5(2) . . ?
N3 C10 C4 130.5(2) . . ?
C5 C10 C4 119.1(2) . . ?
C19 C11 C4 120.6(2) . . ?
C17 C12 C8 113.2(2) . . ?
N2 C13 C5 104.7(2) . . ?
N2 C13 C7 135.7(2) . . ?
C5 C13 C7 119.6(2) . . ?
C8 C14 C23 113.3(2) . . ?
C7 C15 C22 123.8(2) . . ?
O C16 C9 121.6(2) . . ?
O C16 C6 121.6(2) . . ?
C9 C16 C6 116.8(2) . . ?
C20 C17 C12 113.4(2) . . ?
C21 C18 C6 121.5(3) . . ?
C11 C19 C21 120.4(2) . . ?
N2 C20 C17 112.7(2) . . ?
C18 C21 C19 119.6(3) . . ?
C9 C22 C15 119.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N2 N3 C10 1.3(3) . . . . ?
C20 N2 N3 C10 175.4(2) . . . . ?
C11 C4 C6 C18 0.6(4) . . . . ?
C10 C4 C6 C18 179.7(2) . . . . ?
C11 C4 C6 C16 179.8(2) . . . . ?
C10 C4 C6 C16 -1.1(4) . . . . ?
C13 C5 C9 C22 0.1(4) . . . . ?
C10 C5 C9 C22 -179.4(2) . . . . ?
C13 C5 C9 C16 -179.9(2) . . . . ?
C10 C5 C9 C16 0.6(4) . . . . ?
N2 N3 C10 C5 -1.0(3) . . . . ?
N2 N3 C10 C4 178.0(2) . . . . ?
C13 C5 C10 N3 0.4(3) . . . . ?
C9 C5 C10 N3 180.0(2) . . . . ?
C13 C5 C10 C4 -178.7(2) . . . . ?
C9 C5 C10 C4 0.9(4) . . . . ?
C11 C4 C10 N3 -0.4(4) . . . . ?
C6 C4 C10 N3 -179.5(2) . . . . ?
C11 C4 C10 C5 178.5(2) . . . . ?
C6 C4 C10 C5 -0.6(3) . . . . ?
C6 C4 C11 C19 -0.4(4) . . . . ?
C10 C4 C11 C19 -179.4(2) . . . . ?
C14 C8 C12 C17 -170.4(2) . . . . ?
N3 N2 C13 C5 -1.1(3) . . . . ?
C20 N2 C13 C5 -174.5(2) . . . . ?
N3 N2 C13 C7 -179.2(3) . . . . ?
C20 N2 C13 C7 7.3(5) . . . . ?
C9 C5 C13 N2 -179.2(2) . . . . ?
C10 C5 C13 N2 0.4(3) . . . . ?
C9 C5 C13 C7 -0.7(4) . . . . ?
C10 C5 C13 C7 178.9(2) . . . . ?
C15 C7 C13 N2 178.5(3) . . . . ?
C15 C7 C13 C5 0.5(4) . . . . ?
C12 C8 C14 C23 -179.1(2) . . . . ?
C13 C7 C15 C22 0.2(4) . . . . ?
C22 C9 C16 O -1.3(4) . . . . ?
C5 C9 C16 O 178.7(2) . . . . ?
C22 C9 C16 C6 177.9(2) . . . . ?
C5 C9 C16 C6 -2.1(3) . . . . ?
C18 C6 C16 O 0.8(4) . . . . ?
C4 C6 C16 O -178.4(2) . . . . ?
C18 C6 C16 C9 -178.3(2) . . . . ?
C4 C6 C16 C9 2.5(4) . . . . ?
C8 C12 C17 C20 176.1(2) . . . . ?
C4 C6 C18 C21 -0.5(4) . . . . ?
C16 C6 C18 C21 -179.7(2) . . . . ?
C4 C11 C19 C21 0.1(4) . . . . ?
N3 N2 C20 C17 -65.0(3) . . . . ?
C13 N2 C20 C17 108.0(3) . . . . ?
C12 C17 C20 N2 -176.6(2) . . . . ?
C6 C18 C21 C19 0.2(4) . . . . ?
C11 C19 C21 C18 0.0(4) . . . . ?
C5 C9 C22 C15 0.6(4) . . . . ?
C16 C9 C22 C15 -179.4(2) . . . . ?
C7 C15 C22 C9 -0.7(4) . . . . ?

#===END
_database_code_depnum_ccdc_archive 'CCDC 1005085'
