# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1041631'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N O2'
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42

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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   9.8585(16)
_cell_length_b                   11.222(2)
_cell_length_c                   17.434(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1928.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4373
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19152
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3526
_reflns_number_gt                2205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_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)+(0.0721P)²+0.3527P] where P=(Fo²+2Fc²)/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_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(4)
_refine_ls_number_reflns         3526
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0897
_refine_ls_wR_factor_ref         0.1924
_refine_ls_wR_factor_gt          0.1712
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.3112(4) 0.8899(3) 0.4123(3) 0.0836(13) Uani 1 1 d . . .
H1A H 0.382(6) 0.891(5) 0.433(4) 0.100 Uiso 1 1 d . . .
O2 O 0.0728(3) 0.5740(3) 0.5200(2) 0.0750(10) Uani 1 1 d . . .
N1 N 0.4582(4) 0.6274(4) 0.3781(2) 0.0591(10) Uani 1 1 d . . .
C1 C 0.5480(5) 0.6646(4) 0.3173(3) 0.0572(12) Uani 1 1 d . . .
C2 C 0.5713(5) 0.5892(5) 0.2562(3) 0.0693(14) Uani 1 1 d . . .
H2 H 0.5289 0.5153 0.2537 0.083 Uiso 1 1 calc R . .
C3 C 0.6592(6) 0.6254(6) 0.1986(3) 0.0815(16) Uani 1 1 d . . .
H3 H 0.6758 0.5743 0.1577 0.098 Uiso 1 1 calc R . .
C4 C 0.7225(5) 0.7346(5) 0.2003(3) 0.0679(14) Uani 1 1 d . . .
C5 C 0.6951(5) 0.8078(5) 0.2611(3) 0.0700(14) Uani 1 1 d . . .
H5 H 0.7362 0.8824 0.2627 0.084 Uiso 1 1 calc R . .
C6 C 0.6086(5) 0.7754(5) 0.3205(3) 0.0627(13) Uani 1 1 d . . .
H6 H 0.5920 0.8269 0.3612 0.075 Uiso 1 1 calc R . .
C7 C 0.8217(6) 0.7710(6) 0.1388(3) 0.101(2) Uani 1 1 d . . .
H7A H 0.9061 0.7300 0.1464 0.152 Uiso 1 1 calc R . .
H7B H 0.8366 0.8554 0.1414 0.152 Uiso 1 1 calc R . .
H7C H 0.7855 0.7507 0.0893 0.152 Uiso 1 1 calc R . .
C8 C 0.3365(4) 0.6790(4) 0.3959(3) 0.0565(12) Uani 1 1 d . . .
C9 C 0.2808(5) 0.7910(4) 0.3637(3) 0.0620(13) Uani 1 1 d . . .
H9 H 0.3185 0.8047 0.3124 0.074 Uiso 1 1 calc R . .
C10 C 0.1259(5) 0.7796(5) 0.3587(3) 0.0666(14) Uani 1 1 d . . .
C11 C 0.0712(4) 0.7445(4) 0.4376(3) 0.0721(15) Uani 1 1 d . . .
H11A H 0.0845 0.8110 0.4724 0.087 Uiso 1 1 calc R . .
H11B H -0.0257 0.7311 0.4333 0.087 Uiso 1 1 calc R . .
C12 C 0.1352(5) 0.6352(5) 0.4723(3) 0.0646(13) Uani 1 1 d . . .
C13 C 0.2715(5) 0.6075(4) 0.4483(3) 0.0576(12) Uani 1 1 d . . .
C14 C 0.0877(6) 0.6865(5) 0.2983(3) 0.0895(18) Uani 1 1 d . . .
H14A H 0.1212 0.6099 0.3139 0.134 Uiso 1 1 calc R . .
H14B H 0.1273 0.7080 0.2499 0.134 Uiso 1 1 calc R . .
H14C H -0.0091 0.6833 0.2933 0.134 Uiso 1 1 calc R . .
C15 C 0.0632(6) 0.9005(5) 0.3367(4) 0.093(2) Uani 1 1 d . . .
H15A H -0.0336 0.8928 0.3335 0.140 Uiso 1 1 calc R . .
H15B H 0.0983 0.9255 0.2879 0.140 Uiso 1 1 calc R . .
H15C H 0.0859 0.9587 0.3750 0.140 Uiso 1 1 calc R . .
C17 C 0.3571(4) 0.5087(4) 0.4643(3) 0.0603(13) Uani 1 1 d . . .
H17 H 0.3384 0.4469 0.4982 0.072 Uiso 1 1 calc R . .
C18 C 0.4710(5) 0.5205(4) 0.4211(3) 0.0609(13) Uani 1 1 d . . .
C19 C 0.5893(5) 0.4418(4) 0.4166(3) 0.0586(13) Uani 1 1 d . . .
C20 C 0.5676(5) 0.3198(4) 0.4156(3) 0.0676(14) Uani 1 1 d . . .
H20 H 0.4794 0.2904 0.4151 0.081 Uiso 1 1 calc R . .
C21 C 0.6754(6) 0.2417(5) 0.4153(3) 0.0743(15) Uani 1 1 d . . .
H21 H 0.6592 0.1600 0.4143 0.089 Uiso 1 1 calc R . .
C22 C 0.8057(6) 0.2829(5) 0.4164(3) 0.0758(15) Uani 1 1 d . . .
H22 H 0.8781 0.2297 0.4160 0.091 Uiso 1 1 calc R . .
C23 C 0.8288(5) 0.4022(5) 0.4181(3) 0.0780(16) Uani 1 1 d . . .
H23 H 0.9173 0.4308 0.4191 0.094 Uiso 1 1 calc R . .
C24 C 0.7217(5) 0.4810(5) 0.4181(3) 0.0733(15) Uani 1 1 d . . .
H24 H 0.7392 0.5624 0.4192 0.088 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 C9 1.430(6) . ?
O1 H1A 0.78(6) . ?
O2 C12 1.242(6) . ?
N1 C8 1.368(5) . ?
N1 C18 1.421(6) . ?
N1 C1 1.443(6) . ?
C1 C2 1.380(7) . ?
C1 C6 1.381(6) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(7) . ?
C4 C7 1.509(7) . ?
C5 C6 1.390(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.374(6) . ?
C8 C9 1.483(6) . ?
C9 C10 1.535(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.529(7) . ?
C10 C14 1.530(7) . ?
C10 C15 1.539(7) . ?
C11 C12 1.507(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.442(6) . ?
C13 C17 1.421(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.358(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.465(6) . ?
C19 C24 1.378(6) . ?
C19 C20 1.385(6) . ?
C20 C21 1.378(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.359(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C9 O1 H1A 118(5) . . ?
C8 N1 C18 108.4(4) . . ?
C8 N1 C1 125.6(4) . . ?
C18 N1 C1 125.3(4) . . ?
C2 C1 C6 120.8(4) . . ?
C2 C1 N1 119.5(4) . . ?
C6 C1 N1 119.7(4) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 117.6(5) . . ?
C5 C4 C7 121.0(6) . . ?
C3 C4 C7 121.4(6) . . ?
C4 C5 C6 122.7(5) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C5 118.1(5) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C13 108.2(4) . . ?
N1 C8 C9 126.7(4) . . ?
C13 C8 C9 125.0(4) . . ?
O1 C9 C8 110.8(4) . . ?
O1 C9 C10 107.9(4) . . ?
C8 C9 C10 108.7(4) . . ?
O1 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C11 C10 C14 110.9(4) . . ?
C11 C10 C9 108.7(4) . . ?
C14 C10 C9 109.9(4) . . ?
C11 C10 C15 108.0(4) . . ?
C14 C10 C15 109.4(4) . . ?
C9 C10 C15 109.9(4) . . ?
C12 C11 C10 115.1(4) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O2 C12 C13 122.5(5) . . ?
O2 C12 C11 120.8(4) . . ?
C13 C12 C11 116.7(5) . . ?
C8 C13 C17 108.0(4) . . ?
C8 C13 C12 120.1(5) . . ?
C17 C13 C12 131.7(5) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C17 C13 107.8(4) . . ?
C18 C17 H17 126.1 . . ?
C13 C17 H17 126.1 . . ?
C17 C18 N1 107.6(4) . . ?
C17 C18 C19 129.0(4) . . ?
N1 C18 C19 123.5(4) . . ?
C24 C19 C20 117.5(5) . . ?
C24 C19 C18 124.1(4) . . ?
C20 C19 C18 118.2(4) . . ?
C21 C20 C19 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 119.4(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.3(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 121.4(5) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?

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
C8 N1 C1 C2 -114.6(5) . . . . ?
C18 N1 C1 C2 54.7(7) . . . . ?
C8 N1 C1 C6 64.9(6) . . . . ?
C18 N1 C1 C6 -125.8(5) . . . . ?
C6 C1 C2 C3 1.4(7) . . . . ?
N1 C1 C2 C3 -179.1(4) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C2 C3 C4 C7 177.8(5) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C7 C4 C5 C6 -177.3(5) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
N1 C1 C6 C5 179.6(4) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
C18 N1 C8 C13 -0.5(5) . . . . ?
C1 N1 C8 C13 170.3(4) . . . . ?
C18 N1 C8 C9 -179.1(5) . . . . ?
C1 N1 C8 C9 -8.3(7) . . . . ?
N1 C8 C9 O1 -95.1(6) . . . . ?
C13 C8 C9 O1 86.5(6) . . . . ?
N1 C8 C9 C10 146.6(5) . . . . ?
C13 C8 C9 C10 -31.9(7) . . . . ?
O1 C9 C10 C11 -66.6(5) . . . . ?
C8 C9 C10 C11 53.6(5) . . . . ?
O1 C9 C10 C14 171.9(4) . . . . ?
C8 C9 C10 C14 -67.9(6) . . . . ?
O1 C9 C10 C15 51.5(6) . . . . ?
C8 C9 C10 C15 171.7(4) . . . . ?
C14 C10 C11 C12 67.2(5) . . . . ?
C9 C10 C11 C12 -53.7(6) . . . . ?
C15 C10 C11 C12 -172.9(4) . . . . ?
C10 C11 C12 O2 -154.5(5) . . . . ?
C10 C11 C12 C13 26.4(6) . . . . ?
N1 C8 C13 C17 0.7(5) . . . . ?
C9 C8 C13 C17 179.4(4) . . . . ?
N1 C8 C13 C12 -174.7(4) . . . . ?
C9 C8 C13 C12 4.0(7) . . . . ?
O2 C12 C13 C8 -179.4(5) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
O2 C12 C13 C17 6.5(8) . . . . ?
C11 C12 C13 C17 -174.4(5) . . . . ?
C8 C13 C17 C18 -0.7(5) . . . . ?
C12 C13 C17 C18 173.9(5) . . . . ?
C13 C17 C18 N1 0.4(5) . . . . ?
C13 C17 C18 C19 -179.7(5) . . . . ?
C8 N1 C18 C17 0.0(5) . . . . ?
C1 N1 C18 C17 -170.8(4) . . . . ?
C8 N1 C18 C19 -179.9(4) . . . . ?
C1 N1 C18 C19 9.2(7) . . . . ?
C17 C18 C19 C24 -134.5(6) . . . . ?
N1 C18 C19 C24 45.4(7) . . . . ?
C17 C18 C19 C20 41.3(8) . . . . ?
N1 C18 C19 C20 -138.8(5) . . . . ?
C24 C19 C20 C21 -0.7(8) . . . . ?
C18 C19 C20 C21 -176.8(5) . . . . ?
C19 C20 C21 C22 0.4(8) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C21 C22 C23 C24 -0.4(9) . . . . ?
C22 C23 C24 C19 0.1(9) . . . . ?
C20 C19 C24 C23 0.4(8) . . . . ?
C18 C19 C24 C23 176.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
