# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_r141219c1
_database_code_depnum_ccdc_archive 'CCDC 1470929'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_weight         289.36

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                   8.4198(17)
_cell_length_b                   9.6730(19)
_cell_length_c                   11.146(2)
_cell_angle_alpha                113.95(3)
_cell_angle_beta                 96.34(3)
_cell_angle_gamma                106.00(3)
_cell_volume                     771.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2146
_cell_measurement_theta_min      2.0668
_cell_measurement_theta_max      27.9103

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7158
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.96
_reflns_number_total             3498
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0520P)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_coef       0.153(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3498
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.31544(10) 0.51154(9) -0.27170(8) 0.0211(2) Uani 1 1 d . . .
N1 N 0.45897(13) 0.74811(11) 0.18465(9) 0.0185(2) Uani 1 1 d . . .
C1 C 0.63522(16) 0.61354(14) -0.32410(12) 0.0207(3) Uani 1 1 d . . .
H1 H 0.5642 0.5047 -0.3832 0.025 Uiso 1 1 calc R . .
C2 C 0.77796(16) 0.68578(14) -0.35787(12) 0.0234(3) Uani 1 1 d . . .
H2 H 0.8046 0.6263 -0.4396 0.028 Uiso 1 1 calc R . .
C3 C 0.88154(16) 0.84446(14) -0.27242(12) 0.0218(3) Uani 1 1 d . . .
H3 H 0.9804 0.8933 -0.2948 0.026 Uiso 1 1 calc R . .
C4 C 0.84118(16) 0.93214(14) -0.15432(12) 0.0218(3) Uani 1 1 d . . .
H4 H 0.9112 1.0417 -0.0967 0.026 Uiso 1 1 calc R . .
C5 C 0.69848(15) 0.86021(13) -0.11987(11) 0.0190(3) Uani 1 1 d . . .
H5 H 0.6713 0.9208 -0.0388 0.023 Uiso 1 1 calc R . .
C6 C 0.59523(15) 0.69964(13) -0.20391(11) 0.0168(3) Uani 1 1 d . . .
C7 C 0.43417(15) 0.61980(13) -0.17513(11) 0.0167(3) Uani 1 1 d . . .
C8 C 0.41606(14) 0.67323(13) -0.03636(11) 0.0168(3) Uani 1 1 d . . .
C9 C 0.53875(15) 0.72103(13) 0.08128(11) 0.0166(3) Uani 1 1 d . . .
C10 C 0.72074(15) 0.73140(14) 0.10394(12) 0.0197(3) Uani 1 1 d . . .
H10A H 0.7958 0.8452 0.1517 0.030 Uiso 1 1 calc R . .
H10B H 0.7459 0.6788 0.0163 0.030 Uiso 1 1 calc R . .
H10C H 0.7399 0.6770 0.1587 0.030 Uiso 1 1 calc R . .
C11 C 0.28936(15) 0.72129(14) 0.13566(12) 0.0217(3) Uani 1 1 d . . .
H11 H 0.2087 0.7353 0.1886 0.026 Uiso 1 1 calc R . .
C12 C 0.25632(15) 0.67162(13) -0.00051(12) 0.0196(3) Uani 1 1 d . . .
C13 C 0.08861(16) 0.63016(16) -0.09273(13) 0.0287(3) Uani 1 1 d . . .
H13A H 0.0042 0.6467 -0.0396 0.043 Uiso 1 1 calc R . .
H13B H 0.0495 0.5168 -0.1614 0.043 Uiso 1 1 calc R . .
H13C H 0.1024 0.6998 -0.1376 0.043 Uiso 1 1 calc R . .
C14 C 0.54036(16) 0.80684(13) 0.32705(11) 0.0206(3) Uani 1 1 d . . .
H14A H 0.6066 0.7390 0.3338 0.025 Uiso 1 1 calc R . .
H14B H 0.4507 0.7947 0.3763 0.025 Uiso 1 1 calc R . .
C15 C 0.65839(15) 0.98197(13) 0.39514(11) 0.0171(3) Uani 1 1 d . . .
C16 C 0.62704(16) 1.09423(14) 0.35764(11) 0.0210(3) Uani 1 1 d . . .
H16 H 0.5311 1.0610 0.2857 0.025 Uiso 1 1 calc R . .
C17 C 0.73490(16) 1.25459(14) 0.42451(12) 0.0230(3) Uani 1 1 d . . .
H17 H 0.7125 1.3307 0.3983 0.028 Uiso 1 1 calc R . .
C18 C 0.87586(16) 1.30461(14) 0.52989(12) 0.0227(3) Uani 1 1 d . . .
H18 H 0.9493 1.4147 0.5759 0.027 Uiso 1 1 calc R . .
C19 C 0.90848(16) 1.19313(14) 0.56727(11) 0.0230(3) Uani 1 1 d . . .
H19 H 1.0052 1.2262 0.6385 0.028 Uiso 1 1 calc R . .
C20 C 0.79968(16) 1.03286(15) 0.50051(12) 0.0211(3) Uani 1 1 d . . .
H20 H 0.8220 0.9569 0.5271 0.025 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 C7 1.2346(15) . ?
N1 C9 1.3675(14) . ?
N1 C11 1.3832(16) . ?
N1 C14 1.4574(16) . ?
C1 C2 1.3873(17) . ?
C1 C6 1.3964(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3838(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3852(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3903(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3928(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5027(16) . ?
C7 C8 1.4592(15) . ?
C8 C9 1.3948(17) . ?
C8 C12 1.4426(16) . ?
C9 C10 1.4937(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3611(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4978(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5147(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.3876(16) . ?
C15 C20 1.3914(18) . ?
C16 C17 1.3862(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3914(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3837(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3878(18) . ?
C19 H19 0.9500 . ?
C20 H20 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
C9 N1 C11 109.71(10) . . ?
C9 N1 C14 125.90(10) . . ?
C11 N1 C14 124.26(10) . . ?
C2 C1 C6 120.48(11) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.00(11) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.04(11) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.18(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.21(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.07(11) . . ?
C5 C6 C7 122.07(10) . . ?
C1 C6 C7 118.68(11) . . ?
O1 C7 C8 120.67(10) . . ?
O1 C7 C6 118.60(10) . . ?
C8 C7 C6 120.70(10) . . ?
C9 C8 C12 107.77(10) . . ?
C9 C8 C7 128.32(11) . . ?
C12 C8 C7 123.73(11) . . ?
N1 C9 C8 107.04(10) . . ?
N1 C9 C10 121.07(11) . . ?
C8 C9 C10 131.66(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 109.19(11) . . ?
C12 C11 H11 125.4 . . ?
N1 C11 H11 125.4 . . ?
C11 C12 C8 106.24(11) . . ?
C11 C12 C13 126.47(11) . . ?
C8 C12 C13 127.25(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.32(10) . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C20 118.99(11) . . ?
C16 C15 C14 121.77(11) . . ?
C20 C15 C14 119.22(11) . . ?
C17 C16 C15 120.37(12) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.31(12) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.63(12) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 119.88(12) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C15 120.83(12) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?

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
C6 C1 C2 C3 -0.23(19) . . . . ?
C1 C2 C3 C4 -1.11(19) . . . . ?
C2 C3 C4 C5 1.25(18) . . . . ?
C3 C4 C5 C6 -0.03(18) . . . . ?
C4 C5 C6 C1 -1.29(18) . . . . ?
C4 C5 C6 C7 -176.32(10) . . . . ?
C2 C1 C6 C5 1.43(18) . . . . ?
C2 C1 C6 C7 176.63(11) . . . . ?
C5 C6 C7 O1 149.64(12) . . . . ?
C1 C6 C7 O1 -25.41(16) . . . . ?
C5 C6 C7 C8 -28.07(16) . . . . ?
C1 C6 C7 C8 156.88(11) . . . . ?
O1 C7 C8 C9 143.22(12) . . . . ?
C6 C7 C8 C9 -39.11(16) . . . . ?
O1 C7 C8 C12 -31.20(16) . . . . ?
C6 C7 C8 C12 146.47(11) . . . . ?
C11 N1 C9 C8 -1.03(12) . . . . ?
C14 N1 C9 C8 -177.18(10) . . . . ?
C11 N1 C9 C10 -176.25(10) . . . . ?
C14 N1 C9 C10 7.60(16) . . . . ?
C12 C8 C9 N1 -0.19(12) . . . . ?
C7 C8 C9 N1 -175.32(10) . . . . ?
C12 C8 C9 C10 174.32(11) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C9 N1 C11 C12 1.94(13) . . . . ?
C14 N1 C11 C12 178.16(10) . . . . ?
N1 C11 C12 C8 -1.98(13) . . . . ?
N1 C11 C12 C13 -179.81(11) . . . . ?
C9 C8 C12 C11 1.34(13) . . . . ?
C7 C8 C12 C11 176.75(10) . . . . ?
C9 C8 C12 C13 179.16(11) . . . . ?
C7 C8 C12 C13 -5.43(18) . . . . ?
C9 N1 C14 C15 69.82(15) . . . . ?
C11 N1 C14 C15 -105.80(13) . . . . ?
N1 C14 C15 C16 32.08(15) . . . . ?
N1 C14 C15 C20 -149.62(11) . . . . ?
C20 C15 C16 C17 -0.12(17) . . . . ?
C14 C15 C16 C17 178.18(11) . . . . ?
C15 C16 C17 C18 0.06(18) . . . . ?
C16 C17 C18 C19 0.34(18) . . . . ?
C17 C18 C19 C20 -0.66(17) . . . . ?
C18 C19 C20 C15 0.61(17) . . . . ?
C16 C15 C20 C19 -0.21(17) . . . . ?
C14 C15 C20 C19 -178.56(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
