# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_Compound_I
_database_code_depnum_ccdc_archive 'CCDC 1056378'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#-----------------------------------------------------------------------------
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
#-----------------------------------------------------------------------------
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 N O'
_chemical_formula_sum            'C23 H29 N O'
_chemical_formula_weight         335.47

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           Monoclinic
_symmetry_space_group_name_H-M   'P 2/c'
_symmetry_space_group_name_Hall  '-P 2yc'

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

_cell_length_a                   12.8075(5)
_cell_length_b                   9.6355(3)
_cell_length_c                   15.8732(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.6590(18)
_cell_angle_gamma                90.00
_cell_volume                     1945.64(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4494
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9864
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Nonius APEX2 CCD'
_diffrn_measurement_method       ' ω and φ scans '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8223
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4461
_reflns_number_gt                3397
_reflns_threshold_expression     >2sigma(I)

_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)+(0.0633P)²+1.4999P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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 0.66615(12) 0.06920(17) -0.12253(8) 0.0443(4) Uani 1 1 d . . .
N1 N 0.61454(12) -0.12585(17) 0.09830(9) 0.0288(4) Uani 1 1 d . . .
C1 C 0.56951(14) -0.17839(19) 0.02113(11) 0.0279(4) Uani 1 1 d . . .
C2 C 0.50365(16) -0.2957(2) 0.01707(12) 0.0346(4) Uani 1 1 d . . .
H2 H 0.4912 -0.3419 0.0678 0.042 Uiso 1 1 calc R . .
C3 C 0.45754(17) -0.3438(2) -0.05920(13) 0.0377(5) Uani 1 1 d . . .
H3 H 0.4125 -0.4223 -0.0604 0.045 Uiso 1 1 calc R . .
C4 C 0.47484(16) -0.2806(2) -0.13521(13) 0.0385(5) Uani 1 1 d . . .
H4 H 0.4424 -0.3154 -0.1879 0.046 Uiso 1 1 calc R . .
C5 C 0.53934(16) -0.1678(2) -0.13240(12) 0.0354(5) Uani 1 1 d . . .
H5 H 0.5522 -0.1244 -0.1839 0.043 Uiso 1 1 calc R . .
C6 C 0.58717(14) -0.1143(2) -0.05523(11) 0.0293(4) Uani 1 1 d . . .
C7 C 0.65302(15) 0.0087(2) -0.05604(11) 0.0316(4) Uani 1 1 d . . .
C8 C 0.70144(15) 0.0554(2) 0.02637(11) 0.0302(4) Uani 1 1 d . . .
C9 C 0.76832(17) 0.1709(2) 0.03112(13) 0.0386(5) Uani 1 1 d . . .
H9 H 0.7811 0.2168 -0.0197 0.046 Uiso 1 1 calc R . .
C10 C 0.81560(18) 0.2192(2) 0.10700(14) 0.0437(5) Uani 1 1 d . . .
H10 H 0.8605 0.2980 0.1093 0.052 Uiso 1 1 calc R . .
C11 C 0.79676(17) 0.1509(2) 0.18070(13) 0.0411(5) Uani 1 1 d . . .
H11 H 0.8297 0.1837 0.2337 0.049 Uiso 1 1 calc R . .
C12 C 0.73222(16) 0.0378(2) 0.17922(12) 0.0342(4) Uani 1 1 d . . .
H12 H 0.7212 -0.0070 0.2307 0.041 Uiso 1 1 calc R . .
C13 C 0.68186(14) -0.0127(2) 0.10139(11) 0.0290(4) Uani 1 1 d . . .
C14 C 0.59878(15) -0.1982(2) 0.17726(11) 0.0302(4) Uani 1 1 d . . .
H14A H 0.5278 -0.2403 0.1714 0.036 Uiso 1 1 calc R . .
H14B H 0.6028 -0.1304 0.2243 0.036 Uiso 1 1 calc R . .
C15 C 0.68028(16) -0.3108(2) 0.19856(12) 0.0354(4) Uani 1 1 d . . .
H15A H 0.7512 -0.2691 0.2011 0.042 Uiso 1 1 calc R . .
H15B H 0.6737 -0.3805 0.1525 0.042 Uiso 1 1 calc R . .
C16 C 0.67008(16) -0.3835(2) 0.28210(12) 0.0341(4) Uani 1 1 d . . .
H16A H 0.6676 -0.3129 0.3272 0.041 Uiso 1 1 calc R . .
H16B H 0.6031 -0.4357 0.2772 0.041 Uiso 1 1 calc R . .
C17 C 0.76004(19) -0.4824(3) 0.30752(13) 0.0459(6) Uani 1 1 d . . .
H17A H 0.7562 -0.5596 0.2661 0.055 Uiso 1 1 calc R . .
H17B H 0.8271 -0.4328 0.3040 0.055 Uiso 1 1 calc R . .
C18 C 0.76158(17) -0.5428(2) 0.39570(13) 0.0402(5) Uani 1 1 d . . .
H18A H 0.7593 -0.4658 0.4367 0.048 Uiso 1 1 calc R . .
H18B H 0.6975 -0.5996 0.3978 0.048 Uiso 1 1 calc R . .
C19 C 0.8566(2) -0.6312(3) 0.42263(15) 0.0596(7) Uani 1 1 d . . .
H19A H 0.8559 -0.7115 0.3837 0.072 Uiso 1 1 calc R . .
H19B H 0.9204 -0.5762 0.4160 0.072 Uiso 1 1 calc R . .
C20 C 0.86463(18) -0.6847(3) 0.51182(14) 0.0475(6) Uani 1 1 d . . .
H20A H 0.8019 -0.7422 0.5180 0.057 Uiso 1 1 calc R . .
H20B H 0.8634 -0.6047 0.5508 0.057 Uiso 1 1 calc R . .
C21 C 0.9614(2) -0.7695(3) 0.53859(16) 0.0621(8) Uani 1 1 d . . .
H21A H 0.9633 -0.8476 0.4983 0.075 Uiso 1 1 calc R . .
H21B H 1.0237 -0.7108 0.5332 0.075 Uiso 1 1 calc R . .
C22 C 0.9715(2) -0.8269(3) 0.62511(18) 0.0649(8) Uani 1 1 d . . .
H22A H 0.9076 -0.8818 0.6316 0.078 Uiso 1 1 calc R . .
H22B H 0.9735 -0.7487 0.6657 0.078 Uiso 1 1 calc R . .
C23 C 1.0654(2) -0.9168(3) 0.64937(17) 0.0670(8) Uani 1 1 d . . .
H23A H 1.0605 -0.9579 0.7053 0.080 Uiso 1 1 calc R . .
H23B H 1.1294 -0.8606 0.6515 0.080 Uiso 1 1 calc R . .
H23C H 1.0677 -0.9908 0.6073 0.080 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 1.234(2) . ?
N1 C1 1.388(2) . ?
N1 C13 1.388(2) . ?
N1 C14 1.469(2) . ?
C1 C6 1.402(2) . ?
C1 C2 1.408(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(3) . ?
C7 C8 1.453(2) . ?
C8 C9 1.401(3) . ?
C8 C13 1.407(2) . ?
C9 C10 1.366(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.412(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.506(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.499(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.504(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.472(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.496(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C1 N1 C13 120.72(15) . . ?
C1 N1 C14 119.72(16) . . ?
C13 N1 C14 119.31(14) . . ?
N1 C1 C6 120.68(17) . . ?
N1 C1 C2 121.27(16) . . ?
C6 C1 C2 118.05(16) . . ?
C3 C2 C1 120.57(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.51(18) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.57(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 119.67(18) . . ?
C1 C6 C7 121.21(16) . . ?
C5 C6 C7 119.11(17) . . ?
O1 C7 C8 122.49(19) . . ?
O1 C7 C6 121.93(17) . . ?
C8 C7 C6 115.57(16) . . ?
C9 C8 C13 119.50(17) . . ?
C9 C8 C7 119.29(17) . . ?
C13 C8 C7 121.21(18) . . ?
C10 C9 C8 121.61(19) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 121.86(19) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.26(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N1 C13 C8 120.49(16) . . ?
N1 C13 C12 121.37(17) . . ?
C8 C13 C12 118.14(18) . . ?
N1 C14 C15 111.77(15) . . ?
N1 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 113.45(16) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 112.54(17) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 114.60(18) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.79(19) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 115.3(2) . . ?
C20 C19 H19A 108.4 . . ?
C18 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
C18 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 114.7(2) . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C20 116.6(2) . . ?
C22 C21 H21A 108.1 . . ?
C20 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C20 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 116.0(2) . . ?
C21 C22 H22A 108.3 . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22B 108.3 . . ?
C23 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 N1 C1 C6 -3.0(3) . . . . ?
C14 N1 C1 C6 -177.30(16) . . . . ?
C13 N1 C1 C2 178.04(17) . . . . ?
C14 N1 C1 C2 3.7(3) . . . . ?
N1 C1 C2 C3 178.11(18) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
N1 C1 C6 C5 -178.89(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C7 0.1(3) . . . . ?
C2 C1 C6 C7 179.07(17) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -178.36(18) . . . . ?
C1 C6 C7 O1 -177.28(18) . . . . ?
C5 C6 C7 O1 1.7(3) . . . . ?
C1 C6 C7 C8 2.4(3) . . . . ?
C5 C6 C7 C8 -178.65(17) . . . . ?
O1 C7 C8 C9 -2.0(3) . . . . ?
C6 C7 C8 C9 178.33(17) . . . . ?
O1 C7 C8 C13 177.56(18) . . . . ?
C6 C7 C8 C13 -2.1(3) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C10 179.8(2) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C1 N1 C13 C8 3.3(3) . . . . ?
C14 N1 C13 C8 177.61(16) . . . . ?
C1 N1 C13 C12 -176.92(17) . . . . ?
C14 N1 C13 C12 -2.6(3) . . . . ?
C9 C8 C13 N1 178.92(17) . . . . ?
C7 C8 C13 N1 -0.7(3) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C7 C8 C13 C12 179.55(17) . . . . ?
C11 C12 C13 N1 -178.88(18) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C1 N1 C14 C15 86.9(2) . . . . ?
C13 N1 C14 C15 -87.4(2) . . . . ?
N1 C14 C15 C16 177.13(16) . . . . ?
C14 C15 C16 C17 -172.78(18) . . . . ?
C15 C16 C17 C18 172.11(19) . . . . ?
C16 C17 C18 C19 -175.1(2) . . . . ?
C17 C18 C19 C20 175.9(2) . . . . ?
C18 C19 C20 C21 -178.4(2) . . . . ?
C19 C20 C21 C22 -178.6(3) . . . . ?
C20 C21 C22 C23 177.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047


_vrf_PUBL012_GLOBAL              
;
PROBLEM: _publ_section_abstract is missing.
RESPONSE: Will appear in the paper
;
# end Validation Reply Form
####################################################################### 
# 
# 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_Compound_I
_database_code_depnum_ccdc_archive 'CCDC 1056379'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
#-----------------------------------------------------------------------------
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
#-----------------------------------------------------------------------------
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H29 N3'
_chemical_formula_sum            'C26 H29 N3'
_chemical_formula_weight         383.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'

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

_cell_length_a                   13.2115(6)
_cell_length_b                   9.4084(4)
_cell_length_c                   18.0693(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.007(3)
_cell_angle_gamma                90.00
_cell_volume                     2147.78(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4750
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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  'Nonius APEX2 CCD'
_diffrn_measurement_method       ' ω and φ scans '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8571
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4866
_reflns_number_gt                3864
_reflns_threshold_expression     >2sigma(I)

_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)+(0.0480P)²+1.3168P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4866
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
N1 N 0.45102(11) -0.00186(15) 0.33892(8) 0.0297(3) Uani 1 1 d . . .
N2 N 0.35421(15) 0.58882(18) 0.41671(11) 0.0463(4) Uani 1 1 d . . .
N3 N 0.57120(17) 0.60095(19) 0.29836(13) 0.0554(5) Uani 1 1 d . . .
C1 C 0.41473(13) 0.05583(18) 0.39700(10) 0.0283(4) Uani 1 1 d . . .
C2 C 0.35489(14) -0.02588(19) 0.43413(11) 0.0340(4) Uani 1 1 d . . .
H2 H 0.3365 -0.1209 0.4179 0.041 Uiso 1 1 calc R . .
C3 C 0.32299(15) 0.0300(2) 0.49334(12) 0.0366(4) Uani 1 1 d . . .
H3 H 0.2822 -0.0267 0.5175 0.044 Uiso 1 1 calc R . .
C4 C 0.34907(15) 0.1684(2) 0.51893(11) 0.0359(4) Uani 1 1 d . . .
H4 H 0.3278 0.2056 0.5610 0.043 Uiso 1 1 calc R . .
C5 C 0.40560(14) 0.24989(19) 0.48272(10) 0.0328(4) Uani 1 1 d . . .
H5 H 0.4234 0.3444 0.5002 0.039 Uiso 1 1 calc R . .
C6 C 0.43831(13) 0.19847(18) 0.42036(10) 0.0277(4) Uani 1 1 d . . .
C7 C 0.49540(13) 0.28418(17) 0.37958(10) 0.0273(4) Uani 1 1 d . . .
C8 C 0.56073(13) 0.20566(17) 0.34222(9) 0.0263(4) Uani 1 1 d . . .
C9 C 0.64950(14) 0.26491(19) 0.32620(10) 0.0314(4) Uani 1 1 d . . .
H9 H 0.6733 0.3565 0.3459 0.038 Uiso 1 1 calc R . .
C10 C 0.70229(15) 0.1939(2) 0.28305(12) 0.0365(4) Uani 1 1 d . . .
H10 H 0.7614 0.2364 0.2719 0.044 Uiso 1 1 calc R . .
C11 C 0.66865(18) 0.0585(2) 0.25543(13) 0.0439(5) Uani 1 1 d . . .
H11 H 0.7036 0.0103 0.2237 0.053 Uiso 1 1 calc R . .
C12 C 0.58656(17) -0.0056(2) 0.27321(11) 0.0388(4) Uani 1 1 d . . .
H12 H 0.5663 -0.0992 0.2551 0.047 Uiso 1 1 calc R . .
C13 C 0.53142(14) 0.06474(18) 0.31805(10) 0.0284(4) Uani 1 1 d . . .
C14 C 0.39462(15) -0.12354(18) 0.29336(11) 0.0327(4) Uani 1 1 d . . .
H14A H 0.3674 -0.1863 0.3272 0.039 Uiso 1 1 calc R . .
H14B H 0.4445 -0.1794 0.2734 0.039 Uiso 1 1 calc R . .
C15 C 0.30344(15) -0.07320(19) 0.22634(11) 0.0352(4) Uani 1 1 d . . .
H15A H 0.3317 -0.0173 0.1904 0.042 Uiso 1 1 calc R . .
H15B H 0.2576 -0.0097 0.2462 0.042 Uiso 1 1 calc R . .
C16 C 0.23735(15) -0.19481(19) 0.18233(11) 0.0340(4) Uani 1 1 d . . .
H16A H 0.2165 -0.2576 0.2194 0.041 Uiso 1 1 calc R . .
H16B H 0.2808 -0.2515 0.1568 0.041 Uiso 1 1 calc R . .
C17 C 0.13839(15) -0.1437(2) 0.12152(11) 0.0376(4) Uani 1 1 d . . .
H17A H 0.0991 -0.0792 0.1465 0.045 Uiso 1 1 calc R . .
H17B H 0.1600 -0.0879 0.0822 0.045 Uiso 1 1 calc R . .
C18 C 0.06458(16) -0.2611(2) 0.08092(12) 0.0400(5) Uani 1 1 d . . .
H18A H 0.1007 -0.3191 0.0505 0.048 Uiso 1 1 calc R . .
H18B H 0.0492 -0.3238 0.1203 0.048 Uiso 1 1 calc R . .
C19 C -0.03873(16) -0.2067(2) 0.02756(12) 0.0417(5) Uani 1 1 d . . .
H19A H -0.0708 -0.1408 0.0570 0.050 Uiso 1 1 calc R . .
H19B H -0.0233 -0.1514 -0.0145 0.050 Uiso 1 1 calc R . .
C20 C -0.11873(16) -0.3205(2) -0.00827(12) 0.0436(5) Uani 1 1 d . . .
H20A H -0.1348 -0.3756 0.0336 0.052 Uiso 1 1 calc R . .
H20B H -0.0870 -0.3866 -0.0379 0.052 Uiso 1 1 calc R . .
C21 C -0.22130(16) -0.2622(2) -0.06161(12) 0.0441(5) Uani 1 1 d . . .
H21A H -0.2483 -0.1879 -0.0336 0.053 Uiso 1 1 calc R . .
H21B H -0.2060 -0.2164 -0.1065 0.053 Uiso 1 1 calc R . .
C22 C -0.30706(17) -0.3720(3) -0.09124(13) 0.0479(5) Uani 1 1 d . . .
H22A H -0.2798 -0.4475 -0.1185 0.057 Uiso 1 1 calc R . .
H22B H -0.3239 -0.4164 -0.0466 0.057 Uiso 1 1 calc R . .
C23 C -0.4075(2) -0.3122(3) -0.14547(15) 0.0675(8) Uani 1 1 d . . .
H23A H -0.4607 -0.3876 -0.1605 0.081 Uiso 1 1 calc R . .
H23B H -0.3927 -0.2743 -0.1918 0.081 Uiso 1 1 calc R . .
H23C H -0.4342 -0.2359 -0.1194 0.081 Uiso 1 1 calc R . .
C24 C 0.48452(14) 0.43109(18) 0.37315(10) 0.0306(4) Uani 1 1 d . . .
C25 C 0.41082(15) 0.51203(19) 0.39955(11) 0.0339(4) Uani 1 1 d . . .
C26 C 0.53522(16) 0.52001(19) 0.33074(12) 0.0377(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
N1 C13 1.377(2) . ?
N1 C1 1.386(2) . ?
N1 C14 1.478(2) . ?
N2 C25 1.146(2) . ?
N3 C26 1.145(2) . ?
C1 C2 1.406(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(2) . ?
C7 C24 1.391(2) . ?
C7 C8 1.445(2) . ?
C8 C9 1.403(2) . ?
C8 C13 1.414(2) . ?
C9 C10 1.363(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.359(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.513(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.512(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.511(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.509(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.424(2) . ?
C24 C26 1.427(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
C13 N1 C1 119.63(14) . . ?
C13 N1 C14 120.23(15) . . ?
C1 N1 C14 119.70(14) . . ?
N1 C1 C2 120.98(16) . . ?
N1 C1 C6 120.21(15) . . ?
C2 C1 C6 118.82(16) . . ?
C3 C2 C1 120.61(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.18(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.94(18) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 122.09(17) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.27(16) . . ?
C5 C6 C7 123.06(15) . . ?
C1 C6 C7 118.67(15) . . ?
C24 C7 C8 122.03(16) . . ?
C24 C7 C6 122.73(16) . . ?
C8 C7 C6 115.17(14) . . ?
C9 C8 C13 118.60(16) . . ?
C9 C8 C7 122.88(15) . . ?
C13 C8 C7 118.47(15) . . ?
C10 C9 C8 121.44(17) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.35(18) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.96(18) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.77(17) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
N1 C13 C12 121.01(16) . . ?
N1 C13 C8 120.36(15) . . ?
C12 C13 C8 118.63(16) . . ?
N1 C14 C15 110.92(14) . . ?
N1 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 112.66(15) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 112.49(15) . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 114.58(16) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.28(17) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 114.89(17) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 113.50(17) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 114.59(18) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 113.7(2) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 C24 C25 124.58(16) . . ?
C7 C24 C26 125.04(16) . . ?
C25 C24 C26 109.93(15) . . ?
N2 C25 C24 172.9(2) . . ?
N3 C26 C24 174.1(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 N1 C1 C2 -162.62(16) . . . . ?
C14 N1 C1 C2 25.0(2) . . . . ?
C13 N1 C1 C6 16.8(2) . . . . ?
C14 N1 C1 C6 -155.54(15) . . . . ?
N1 C1 C2 C3 177.40(16) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -2.4(3) . . . . ?
C4 C5 C6 C7 178.02(17) . . . . ?
N1 C1 C6 C5 -176.08(15) . . . . ?
C2 C1 C6 C5 3.4(2) . . . . ?
N1 C1 C6 C7 3.5(2) . . . . ?
C2 C1 C6 C7 -177.04(15) . . . . ?
C5 C6 C7 C24 -28.7(3) . . . . ?
C1 C6 C7 C24 151.78(17) . . . . ?
C5 C6 C7 C8 154.47(16) . . . . ?
C1 C6 C7 C8 -25.1(2) . . . . ?
C24 C7 C8 C9 28.1(3) . . . . ?
C6 C7 C8 C9 -154.97(16) . . . . ?
C24 C7 C8 C13 -149.29(17) . . . . ?
C6 C7 C8 C13 27.6(2) . . . . ?
C13 C8 C9 C10 5.1(3) . . . . ?
C7 C8 C9 C10 -172.31(17) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 -2.4(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C1 N1 C13 C12 165.12(16) . . . . ?
C14 N1 C13 C12 -22.5(2) . . . . ?
C1 N1 C13 C8 -14.2(2) . . . . ?
C14 N1 C13 C8 158.09(15) . . . . ?
C11 C12 C13 N1 -177.30(18) . . . . ?
C11 C12 C13 C8 2.1(3) . . . . ?
C9 C8 C13 N1 173.90(16) . . . . ?
C7 C8 C13 N1 -8.5(2) . . . . ?
C9 C8 C13 C12 -5.5(2) . . . . ?
C7 C8 C13 C12 172.07(16) . . . . ?
C13 N1 C14 C15 -86.9(2) . . . . ?
C1 N1 C14 C15 85.47(19) . . . . ?
N1 C14 C15 C16 -174.83(16) . . . . ?
C14 C15 C16 C17 172.91(16) . . . . ?
C15 C16 C17 C18 -174.71(17) . . . . ?
C16 C17 C18 C19 173.37(18) . . . . ?
C17 C18 C19 C20 -174.50(18) . . . . ?
C18 C19 C20 C21 -179.86(18) . . . . ?
C19 C20 C21 C22 -173.57(19) . . . . ?
C20 C21 C22 C23 -178.8(2) . . . . ?
C8 C7 C24 C25 171.10(17) . . . . ?
C6 C7 C24 C25 -5.6(3) . . . . ?
C8 C7 C24 C26 -0.4(3) . . . . ?
C6 C7 C24 C26 -177.05(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045



_vrf_PUBL012_GLOBAL              
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PROBLEM: _publ_section_abstract is missing.
RESPONSE: Will appear in the paper
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# end Validation Reply Form
