# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_uor005
_database_code_depnum_ccdc_archive 'CCDC 1401824'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7936(7)
_cell_length_b                   10.0349(4)
_cell_length_c                   10.3079(6)
_cell_angle_alpha                110.403(5)
_cell_angle_beta                 101.163(6)
_cell_angle_gamma                102.888(5)
_cell_volume                     883.80(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3440
_cell_measurement_theta_min      3.2582
_cell_measurement_theta_max      32.3735

_exptl_crystal_description       block
_exptl_crystal_colour            'golden yellow'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6407
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3110
_reflns_number_gt                2650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0457P)²+0.3142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3110
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
O1 O -0.66319(15) -0.24191(15) 0.66831(14) 0.0572(4) Uani 1 1 d . . .
N1 N -0.19796(17) 0.08810(16) 0.61464(16) 0.0464(4) Uani 1 1 d . . .
N2 N -0.60246(15) -0.32886(15) 0.45264(15) 0.0401(3) Uani 1 1 d . . .
C1 C -0.58451(19) -0.22527(19) 0.59314(18) 0.0411(4) Uani 1 1 d . . .
C2 C -0.71549(18) -0.47044(19) 0.38091(18) 0.0390(4) Uani 1 1 d . . .
C3 C -0.85900(19) -0.4785(2) 0.37992(19) 0.0437(4) Uani 1 1 d . . .
H3 H -0.8823 -0.3900 0.4254 0.052 Uiso 1 1 calc R . .
C4 C -0.9677(2) -0.6157(2) 0.31255(19) 0.0467(4) Uani 1 1 d . . .
H4 H -1.0653 -0.6209 0.3145 0.056 Uiso 1 1 calc R . .
C5 C -0.9374(2) -0.7466(2) 0.2418(2) 0.0472(4) Uani 1 1 d . . .
C6 C -0.7936(2) -0.7357(2) 0.2433(2) 0.0497(5) Uani 1 1 d . . .
H6 H -0.7707 -0.8237 0.1950 0.060 Uiso 1 1 calc R . .
C7 C -0.6826(2) -0.5999(2) 0.3133(2) 0.0467(4) Uani 1 1 d . . .
H7 H -0.5843 -0.5953 0.3150 0.056 Uiso 1 1 calc R . .
C8 C -1.0573(3) -0.8956(2) 0.1670(3) 0.0681(6) Uani 1 1 d . . .
H8A H -1.1393 -0.8900 0.2080 0.102 Uiso 1 1 calc R . .
H8B H -1.0193 -0.9734 0.1814 0.102 Uiso 1 1 calc R . .
H8C H -1.0914 -0.9202 0.0631 0.102 Uiso 1 1 calc R . .
C9 C -0.48545(18) -0.27972(18) 0.40096(17) 0.0370(4) Uani 1 1 d . . .
C10 C -0.44431(19) -0.3398(2) 0.28364(18) 0.0421(4) Uani 1 1 d . . .
H10 H -0.5089 -0.4284 0.2042 0.051 Uiso 1 1 calc R . .
C11 C -0.29350(19) -0.2659(2) 0.27748(18) 0.0428(4) Uani 1 1 d . . .
C12 C -0.1883(2) -0.3353(2) 0.3422(2) 0.0563(5) Uani 1 1 d . . .
H12A H -0.1807 -0.3069 0.4451 0.084 Uiso 1 1 calc R . .
H12B H -0.0912 -0.2984 0.3322 0.084 Uiso 1 1 calc R . .
H12C H -0.2261 -0.4447 0.2906 0.084 Uiso 1 1 calc R . .
C13 C -0.2958(2) -0.3013(2) 0.1198(2) 0.0567(5) Uani 1 1 d . . .
H13A H -0.3304 -0.4101 0.0639 0.085 Uiso 1 1 calc R . .
H13B H -0.1966 -0.2597 0.1166 0.085 Uiso 1 1 calc R . .
H13C H -0.3619 -0.2567 0.0781 0.085 Uiso 1 1 calc R . .
C14 C -0.2372(2) -0.0939(2) 0.36458(19) 0.0461(4) Uani 1 1 d . . .
H14A H -0.1295 -0.0582 0.3844 0.055 Uiso 1 1 calc R . .
H14B H -0.2807 -0.0471 0.3042 0.055 Uiso 1 1 calc R . .
C15 C -0.27229(19) -0.04193(19) 0.50573(18) 0.0406(4) Uani 1 1 d . . .
C16 C -0.39729(18) -0.13562(18) 0.51310(17) 0.0371(4) Uani 1 1 d . . .
C17 C -0.45125(18) -0.09932(18) 0.62784(17) 0.0382(4) Uani 1 1 d . . .
C18 C -0.37494(19) 0.03903(19) 0.74909(18) 0.0405(4) Uani 1 1 d . . .
C19 C -0.4147(2) 0.0904(2) 0.87762(19) 0.0481(5) Uani 1 1 d . . .
H19 H -0.4989 0.0310 0.8877 0.058 Uiso 1 1 calc R . .
C20 C -0.3319(2) 0.2262(2) 0.9881(2) 0.0580(5) Uani 1 1 d . . .
H20 H -0.3584 0.2601 1.0750 0.070 Uiso 1 1 calc R . .
C21 C -0.2088(2) 0.3150(2) 0.9741(2) 0.0595(5) Uani 1 1 d . . .
H21 H -0.1533 0.4097 1.0509 0.071 Uiso 1 1 calc R . .
C22 C -0.1673(2) 0.2675(2) 0.8513(2) 0.0542(5) Uani 1 1 d . . .
H22 H -0.0828 0.3292 0.8439 0.065 Uiso 1 1 calc R . .
C23 C -0.2480(2) 0.12833(19) 0.73536(18) 0.0429(4) 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
O1 C1 1.219(2) . ?
N1 C15 1.316(2) . ?
N1 C23 1.388(2) . ?
N2 C1 1.407(2) . ?
N2 C9 1.417(2) . ?
N2 C2 1.428(2) . ?
C1 C17 1.482(2) . ?
C2 C7 1.385(2) . ?
C2 C3 1.387(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 C8 1.507(3) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.333(2) . ?
C9 C16 1.437(2) . ?
C10 C11 1.522(2) . ?
C10 H10 0.9500 . ?
C11 C13 1.532(2) . ?
C11 C12 1.539(3) . ?
C11 C14 1.547(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.500(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.400(2) . ?
C16 C17 1.356(2) . ?
C17 C18 1.419(2) . ?
C18 C19 1.409(2) . ?
C18 C23 1.424(3) . ?
C19 C20 1.371(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.363(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.408(2) . ?
C22 H22 0.9500 . ?

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
C15 N1 C23 117.78(15) . . ?
C1 N2 C9 110.61(13) . . ?
C1 N2 C2 123.50(14) . . ?
C9 N2 C2 125.58(13) . . ?
O1 C1 N2 125.32(16) . . ?
O1 C1 C17 128.99(16) . . ?
N2 C1 C17 105.67(14) . . ?
C7 C2 C3 119.79(16) . . ?
C7 C2 N2 120.44(15) . . ?
C3 C2 N2 119.77(15) . . ?
C4 C3 C2 119.69(17) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.38(17) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.92(17) . . ?
C6 C5 C8 121.14(18) . . ?
C4 C5 C8 120.94(18) . . ?
C7 C6 C5 121.52(18) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 119.66(17) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N2 134.52(16) . . ?
C10 C9 C16 120.47(15) . . ?
N2 C9 C16 104.93(13) . . ?
C9 C10 C11 119.77(15) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C13 110.16(15) . . ?
C10 C11 C12 106.27(15) . . ?
C13 C11 C12 108.99(15) . . ?
C10 C11 C14 113.35(14) . . ?
C13 C11 C14 108.84(15) . . ?
C12 C11 C14 109.13(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 114.17(14) . . ?
C15 C14 H14A 108.7 . . ?
C11 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C11 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N1 C15 C16 120.49(16) . . ?
N1 C15 C14 123.25(16) . . ?
C16 C15 C14 116.10(15) . . ?
C17 C16 C15 123.55(16) . . ?
C17 C16 C9 111.55(15) . . ?
C15 C16 C9 124.89(15) . . ?
C16 C17 C18 118.48(16) . . ?
C16 C17 C1 107.14(14) . . ?
C18 C17 C1 134.37(15) . . ?
C19 C18 C17 125.16(17) . . ?
C19 C18 C23 119.66(16) . . ?
C17 C18 C23 115.18(15) . . ?
C20 C19 C18 119.93(19) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.55(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.69(18) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.90(19) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
N1 C23 C22 117.24(17) . . ?
N1 C23 C18 124.50(15) . . ?
C22 C23 C18 118.26(16) . . ?

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
C9 N2 C1 O1 -175.38(17) . . . . ?
C2 N2 C1 O1 -1.5(3) . . . . ?
C9 N2 C1 C17 3.12(18) . . . . ?
C2 N2 C1 C17 177.02(15) . . . . ?
C1 N2 C2 C7 -132.15(18) . . . . ?
C9 N2 C2 C7 40.8(2) . . . . ?
C1 N2 C2 C3 47.4(2) . . . . ?
C9 N2 C2 C3 -139.66(17) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
N2 C2 C3 C4 -178.97(15) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 C8 -179.24(18) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C8 C5 C6 C7 -179.10(18) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
N2 C2 C7 C6 -179.42(16) . . . . ?
C1 N2 C9 C10 173.45(19) . . . . ?
C2 N2 C9 C10 -0.3(3) . . . . ?
C1 N2 C9 C16 -3.16(18) . . . . ?
C2 N2 C9 C16 -176.91(15) . . . . ?
N2 C9 C10 C11 -167.81(17) . . . . ?
C16 C9 C10 C11 8.4(3) . . . . ?
C9 C10 C11 C13 -152.78(17) . . . . ?
C9 C10 C11 C12 89.3(2) . . . . ?
C9 C10 C11 C14 -30.6(2) . . . . ?
C10 C11 C14 C15 39.1(2) . . . . ?
C13 C11 C14 C15 162.09(15) . . . . ?
C12 C11 C14 C15 -79.07(19) . . . . ?
C23 N1 C15 C16 -0.2(3) . . . . ?
C23 N1 C15 C14 175.12(16) . . . . ?
C11 C14 C15 N1 157.38(17) . . . . ?
C11 C14 C15 C16 -27.1(2) . . . . ?
N1 C15 C16 C17 1.4(3) . . . . ?
C14 C15 C16 C17 -174.20(16) . . . . ?
N1 C15 C16 C9 -179.60(16) . . . . ?
C14 C15 C16 C9 4.8(3) . . . . ?
C10 C9 C16 C17 -175.23(16) . . . . ?
N2 C9 C16 C17 1.97(19) . . . . ?
C10 C9 C16 C15 5.7(3) . . . . ?
N2 C9 C16 C15 -177.11(15) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C9 C16 C17 C18 178.98(14) . . . . ?
C15 C16 C17 C1 178.99(15) . . . . ?
C9 C16 C17 C1 -0.11(19) . . . . ?
O1 C1 C17 C16 176.60(18) . . . . ?
N2 C1 C17 C16 -1.82(18) . . . . ?
O1 C1 C17 C18 -2.3(3) . . . . ?
N2 C1 C17 C18 179.30(18) . . . . ?
C16 C17 C18 C19 -178.10(16) . . . . ?
C1 C17 C18 C19 0.7(3) . . . . ?
C16 C17 C18 C23 1.2(2) . . . . ?
C1 C17 C18 C23 179.96(17) . . . . ?
C17 C18 C19 C20 179.69(17) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C15 N1 C23 C22 179.83(17) . . . . ?
C15 N1 C23 C18 -0.5(3) . . . . ?
C21 C22 C23 N1 -179.71(18) . . . . ?
C21 C22 C23 C18 0.6(3) . . . . ?
C19 C18 C23 N1 179.29(16) . . . . ?
C17 C18 C23 N1 0.0(3) . . . . ?
C19 C18 C23 C22 -1.0(3) . . . . ?
C17 C18 C23 C22 179.66(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034
