# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ckj_1_236_1
_audit_block_doi                 10.5517/cc10z3kn
_database_code_depnum_ccdc_archive 'CCDC 952461'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C3CC46191B 2014
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-((R)-phenyl((S)-3-phenylmorpholino)methyl)naphthalen-2-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N O2'
_chemical_formula_sum            'C27 H25 N O2'
_chemical_formula_weight         395.48

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   'C 2/c'

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

_cell_length_a                   26.2548(11)
_cell_length_b                   9.6138(6)
_cell_length_c                   17.4876(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.593(4)
_cell_angle_gamma                90.00
_cell_volume                     4290.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9487
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      28.75

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8463
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3785
_reflns_number_gt                2701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0300P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3785
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.41345(6) 0.38319(19) 0.16613(8) 0.0508(5) Uani 1 1 d . . .
H1 H 0.3936 0.4304 0.1330 0.076 Uiso 1 1 calc R . .
O2 O 0.25396(7) 0.4569(2) -0.00856(9) 0.0544(5) Uani 1 1 d . . .
N1 N 0.33714(7) 0.5593(2) 0.11445(9) 0.0373(5) Uani 1 1 d . . .
C10 C 0.42539(8) 0.5250(3) 0.39362(12) 0.0405(6) Uani 1 1 d . . .
C16 C 0.25291(8) 0.5396(3) 0.16464(12) 0.0391(5) Uani 1 1 d . . .
C9 C 0.39702(8) 0.6075(3) 0.32999(11) 0.0370(5) Uani 1 1 d . . .
C11 C 0.36238(8) 0.6493(2) 0.18266(11) 0.0366(5) Uani 1 1 d . . .
H11 H 0.3346 0.6992 0.2001 0.044 Uiso 1 1 calc R . .
C1 C 0.39172(8) 0.5593(3) 0.25097(11) 0.0357(5) Uani 1 1 d . . .
C2 C 0.41560(8) 0.4364(3) 0.23896(12) 0.0403(6) Uani 1 1 d . . .
C22 C 0.39872(9) 0.7565(3) 0.16028(12) 0.0402(6) Uani 1 1 d . . .
C4 C 0.44775(8) 0.3980(3) 0.37716(13) 0.0469(6) Uani 1 1 d . . .
H4 H 0.4656 0.3428 0.4185 0.056 Uiso 1 1 calc R . .
C12 C 0.29536(8) 0.4681(3) 0.13260(12) 0.0401(6) Uani 1 1 d . . .
H12 H 0.3133 0.4046 0.1741 0.048 Uiso 1 1 calc R . .
C3 C 0.44362(8) 0.3558(3) 0.30235(13) 0.0460(6) Uani 1 1 d . . .
H3 H 0.4593 0.2730 0.2926 0.055 Uiso 1 1 calc R . .
C8 C 0.37665(9) 0.7359(3) 0.34919(13) 0.0464(6) Uani 1 1 d . . .
H8 H 0.3576 0.7916 0.3090 0.056 Uiso 1 1 calc R . .
C15 C 0.31685(9) 0.6396(3) 0.04182(12) 0.0446(6) Uani 1 1 d . . .
H15A H 0.3450 0.6936 0.0292 0.054 Uiso 1 1 calc R . .
H15B H 0.2900 0.7035 0.0498 0.054 Uiso 1 1 calc R . .
C17 C 0.25744(9) 0.5412(3) 0.24531(13) 0.0486(6) Uani 1 1 d . . .
H17 H 0.2869 0.5021 0.2784 0.058 Uiso 1 1 calc R . .
C21 C 0.20812(9) 0.5986(3) 0.11727(14) 0.0496(6) Uani 1 1 d . . .
H21 H 0.2040 0.5997 0.0630 0.060 Uiso 1 1 calc R . .
C5 C 0.43173(9) 0.5738(3) 0.47156(13) 0.0504(7) Uani 1 1 d . . .
H5 H 0.4497 0.5191 0.5131 0.061 Uiso 1 1 calc R . .
C14 C 0.29423(10) 0.5429(3) -0.02518(13) 0.0528(7) Uani 1 1 d . . .
H14A H 0.2800 0.5972 -0.0721 0.063 Uiso 1 1 calc R . .
H14B H 0.3219 0.4845 -0.0357 0.063 Uiso 1 1 calc R . .
C7 C 0.38439(10) 0.7798(3) 0.42554(13) 0.0540(7) Uani 1 1 d . . .
H7 H 0.3708 0.8650 0.4364 0.065 Uiso 1 1 calc R . .
C13 C 0.27405(10) 0.3779(3) 0.06086(13) 0.0520(7) Uani 1 1 d . . .
H13A H 0.3018 0.3177 0.0521 0.062 Uiso 1 1 calc R . .
H13B H 0.2464 0.3191 0.0712 0.062 Uiso 1 1 calc R . .
C6 C 0.41237(10) 0.6981(3) 0.48707(13) 0.0548(7) Uani 1 1 d . . .
H6 H 0.4177 0.7291 0.5387 0.066 Uiso 1 1 calc R . .
C18 C 0.21918(10) 0.5995(3) 0.27773(15) 0.0564(7) Uani 1 1 d . . .
H18 H 0.2234 0.6006 0.3320 0.068 Uiso 1 1 calc R . .
C19 C 0.17517(10) 0.6555(3) 0.22997(16) 0.0585(7) Uani 1 1 d . . .
H19 H 0.1491 0.6934 0.2516 0.070 Uiso 1 1 calc R . .
C27 C 0.44727(10) 0.7230(3) 0.14764(15) 0.0562(7) Uani 1 1 d . . .
H27 H 0.4588 0.6313 0.1536 0.067 Uiso 1 1 calc R . .
C20 C 0.16971(10) 0.6555(3) 0.14978(16) 0.0614(8) Uani 1 1 d . . .
H20 H 0.1399 0.6941 0.1172 0.074 Uiso 1 1 calc R . .
C23 C 0.38344(12) 0.8938(3) 0.15283(17) 0.0682(8) Uani 1 1 d . . .
H23 H 0.3509 0.9189 0.1610 0.082 Uiso 1 1 calc R . .
C26 C 0.47879(12) 0.8229(4) 0.12644(19) 0.0788(10) Uani 1 1 d . . .
H26 H 0.5108 0.7979 0.1165 0.095 Uiso 1 1 calc R . .
C24 C 0.41570(15) 0.9954(4) 0.1333(2) 0.0965(12) Uani 1 1 d . . .
H24 H 0.4051 1.0879 0.1294 0.116 Uiso 1 1 calc R . .
C25 C 0.46319(15) 0.9587(4) 0.1200(2) 0.0956(12) Uani 1 1 d . . .
H25 H 0.4849 1.0263 0.1064 0.115 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 C2 1.361(2) . ?
O2 C13 1.424(3) . ?
O2 C14 1.425(3) . ?
N1 C15 1.475(3) . ?
N1 C12 1.495(3) . ?
N1 C11 1.497(3) . ?
C10 C4 1.413(3) . ?
C10 C5 1.414(3) . ?
C10 C9 1.426(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.390(3) . ?
C16 C12 1.524(3) . ?
C9 C8 1.417(3) . ?
C9 C1 1.433(3) . ?
C11 C22 1.517(3) . ?
C11 C1 1.529(3) . ?
C1 C2 1.377(3) . ?
C2 C3 1.410(3) . ?
C22 C23 1.377(4) . ?
C22 C27 1.382(3) . ?
C4 C3 1.350(3) . ?
C12 C13 1.520(3) . ?
C8 C7 1.369(3) . ?
C15 C14 1.504(3) . ?
C17 C18 1.383(3) . ?
C21 C20 1.382(3) . ?
C5 C6 1.351(4) . ?
C7 C6 1.394(4) . ?
C18 C19 1.367(4) . ?
C19 C20 1.376(4) . ?
C27 C26 1.375(4) . ?
C23 C24 1.386(4) . ?
C26 C25 1.365(5) . ?
C24 C25 1.368(5) . ?

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 O2 C14 109.85(18) . . ?
C15 N1 C12 110.80(16) . . ?
C15 N1 C11 112.75(18) . . ?
C12 N1 C11 112.29(15) . . ?
C4 C10 C5 121.5(2) . . ?
C4 C10 C9 119.2(2) . . ?
C5 C10 C9 119.3(2) . . ?
C17 C16 C21 117.4(2) . . ?
C17 C16 C12 118.9(2) . . ?
C21 C16 C12 123.65(19) . . ?
C8 C9 C10 117.2(2) . . ?
C8 C9 C1 123.6(2) . . ?
C10 C9 C1 119.2(2) . . ?
N1 C11 C22 112.00(16) . . ?
N1 C11 C1 110.06(19) . . ?
C22 C11 C1 110.74(17) . . ?
C2 C1 C9 118.7(2) . . ?
C2 C1 C11 122.04(19) . . ?
C9 C1 C11 119.2(2) . . ?
O1 C2 C1 123.0(2) . . ?
O1 C2 C3 115.3(2) . . ?
C1 C2 C3 121.6(2) . . ?
C23 C22 C27 117.9(3) . . ?
C23 C22 C11 119.3(2) . . ?
C27 C22 C11 122.9(2) . . ?
C3 C4 C10 121.0(2) . . ?
N1 C12 C13 107.79(18) . . ?
N1 C12 C16 116.7(2) . . ?
C13 C12 C16 113.70(18) . . ?
C4 C3 C2 120.3(2) . . ?
C7 C8 C9 121.5(2) . . ?
N1 C15 C14 110.1(2) . . ?
C18 C17 C16 121.6(2) . . ?
C20 C21 C16 120.9(2) . . ?
C6 C5 C10 121.5(2) . . ?
O2 C14 C15 112.07(19) . . ?
C8 C7 C6 120.6(3) . . ?
O2 C13 C12 112.9(2) . . ?
C5 C6 C7 119.9(2) . . ?
C19 C18 C17 120.0(2) . . ?
C18 C19 C20 119.5(2) . . ?
C26 C27 C22 121.1(3) . . ?
C19 C20 C21 120.6(2) . . ?
C22 C23 C24 121.1(3) . . ?
C25 C26 C27 120.2(3) . . ?
C25 C24 C23 119.7(3) . . ?
C26 C25 C24 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
####################################################################### 
# 
# 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_ckj_129
_database_code_depnum_ccdc_archive 'CCDC 1499395'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-((R)-phenyl((R)-2-phenylpyrrolidin-1-yl)methyl)naphthalen-2-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N O'
_chemical_formula_sum            'C27 H25 N O'
_chemical_formula_weight         379.48

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 n a 21'

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

_cell_length_a                   13.4796(7)
_cell_length_b                   23.9065(12)
_cell_length_c                   6.3744(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2054.15(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6572
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      28.74

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5614
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3057
_reflns_number_gt                2523
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0019P)²+0.9926P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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 0.69342(17) 0.30291(10) 0.4139(3) 0.0495(6) Uani 1 1 d . . .
H1 H 0.7368 0.3015 0.5039 0.074 Uiso 1 1 calc R . .
N1 N 0.76119(18) 0.30491(10) 0.7936(4) 0.0340(6) Uani 1 1 d . . .
C10 C 0.4499(3) 0.39711(13) 0.5983(6) 0.0440(9) Uani 1 1 d . . .
C2 C 0.6153(2) 0.33360(13) 0.4869(5) 0.0380(8) Uani 1 1 d . . .
C9 C 0.5328(2) 0.39450(12) 0.7348(5) 0.0361(8) Uani 1 1 d . . .
C12 C 0.7749(2) 0.40938(12) 0.7712(5) 0.0349(8) Uani 1 1 d . . .
C11 C 0.7083(2) 0.35948(11) 0.8184(5) 0.0323(7) Uani 1 1 d . . .
H11 H 0.6863 0.3625 0.9644 0.039 Uiso 1 1 calc R . .
C1 C 0.6165(2) 0.36094(12) 0.6776(5) 0.0339(7) Uani 1 1 d . . .
C22 C 0.9442(2) 0.32164(12) 0.7657(6) 0.0397(8) Uani 1 1 d . . .
C17 C 0.8096(2) 0.42016(14) 0.5725(5) 0.0439(8) Uani 1 1 d . . .
H17 H 0.7919 0.3967 0.4623 0.053 Uiso 1 1 calc R . .
C21 C 0.8593(2) 0.30267(12) 0.9032(5) 0.0402(8) Uani 1 1 d . . .
H21 H 0.8567 0.3263 1.0286 0.048 Uiso 1 1 calc R . .
C23 C 1.0124(2) 0.36026(13) 0.8405(6) 0.0475(9) Uani 1 1 d . . .
H23 H 1.0048 0.3750 0.9745 0.057 Uiso 1 1 calc R . .
C24 C 1.0918(3) 0.37702(14) 0.7175(7) 0.0591(11) Uani 1 1 d . . .
H24 H 1.1369 0.4031 0.7688 0.071 Uiso 1 1 calc R . .
C15 C 0.8954(3) 0.50163(15) 0.6954(7) 0.0624(12) Uani 1 1 d . . .
H15 H 0.9355 0.5325 0.6697 0.075 Uiso 1 1 calc R . .
C27 C 0.9577(3) 0.29983(14) 0.5665(6) 0.0514(10) Uani 1 1 d . . .
H27 H 0.9127 0.2739 0.5141 0.062 Uiso 1 1 calc R . .
C18 C 0.7017(2) 0.25789(11) 0.8800(6) 0.0445(8) Uani 1 1 d . . .
H18A H 0.6495 0.2469 0.7837 0.053 Uiso 1 1 calc R . .
H18B H 0.6724 0.2678 1.0139 0.053 Uiso 1 1 calc R . .
C8 C 0.5292(3) 0.42671(12) 0.9229(6) 0.0456(8) Uani 1 1 d . . .
H8 H 0.5823 0.4256 1.0162 0.055 Uiso 1 1 calc R . .
C4 C 0.4515(3) 0.36672(14) 0.4075(6) 0.0526(9) Uani 1 1 d . . .
H4 H 0.3968 0.3678 0.3188 0.063 Uiso 1 1 calc R . .
C13 C 0.8003(3) 0.44564(12) 0.9330(6) 0.0474(9) Uani 1 1 d . . .
H13 H 0.7770 0.4392 1.0682 0.057 Uiso 1 1 calc R . .
C3 C 0.5323(2) 0.33606(14) 0.3533(6) 0.0487(9) Uani 1 1 d . . .
H3 H 0.5328 0.3166 0.2270 0.058 Uiso 1 1 calc R . .
C16 C 0.8708(3) 0.46570(15) 0.5351(6) 0.0576(11) Uani 1 1 d . . .
H16 H 0.8953 0.4720 0.4008 0.069 Uiso 1 1 calc R . .
C5 C 0.3674(3) 0.43123(16) 0.6524(7) 0.0617(11) Uani 1 1 d . . .
H5 H 0.3130 0.4330 0.5630 0.074 Uiso 1 1 calc R . .
C6 C 0.3673(3) 0.46119(16) 0.8332(8) 0.0722(13) Uani 1 1 d . . .
H6 H 0.3126 0.4831 0.8675 0.087 Uiso 1 1 calc R . .
C7 C 0.4485(3) 0.45927(14) 0.9672(7) 0.0611(11) Uani 1 1 d . . .
H7 H 0.4479 0.4805 1.0894 0.073 Uiso 1 1 calc R . .
C14 C 0.8603(3) 0.49139(14) 0.8927(7) 0.0587(11) Uani 1 1 d . . .
H14 H 0.8769 0.5155 1.0016 0.070 Uiso 1 1 calc R . .
C25 C 1.1040(3) 0.35524(16) 0.5206(7) 0.0650(12) Uani 1 1 d . . .
H25 H 1.1571 0.3667 0.4381 0.078 Uiso 1 1 calc R . .
C26 C 1.0376(3) 0.31627(15) 0.4444(7) 0.0604(11) Uani 1 1 d . . .
H26 H 1.0465 0.3011 0.3113 0.072 Uiso 1 1 calc R . .
C20 C 0.8697(3) 0.24056(13) 0.9712(7) 0.0594(10) Uani 1 1 d . . .
H20A H 0.9266 0.2235 0.9038 0.071 Uiso 1 1 calc R . .
H20B H 0.8780 0.2379 1.1220 0.071 Uiso 1 1 calc R . .
C19 C 0.7768(3) 0.21239(13) 0.9047(8) 0.0794(15) Uani 1 1 d . . .
H19A H 0.7555 0.1857 1.0099 0.095 Uiso 1 1 calc R . .
H19B H 0.7866 0.1928 0.7730 0.095 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 C2 1.365(4) . ?
N1 C18 1.486(4) . ?
N1 C11 1.495(3) . ?
N1 C21 1.497(4) . ?
C10 C9 1.417(4) . ?
C10 C4 1.417(5) . ?
C10 C5 1.421(5) . ?
C2 C1 1.380(4) . ?
C2 C3 1.407(4) . ?
C9 C8 1.426(4) . ?
C9 C1 1.432(4) . ?
C12 C17 1.374(4) . ?
C12 C13 1.390(4) . ?
C12 C11 1.523(4) . ?
C11 C1 1.530(4) . ?
C22 C27 1.385(5) . ?
C22 C23 1.388(4) . ?
C22 C21 1.511(4) . ?
C17 C16 1.386(5) . ?
C21 C20 1.553(4) . ?
C23 C24 1.386(5) . ?
C24 C25 1.369(5) . ?
C15 C14 1.366(5) . ?
C15 C16 1.375(5) . ?
C27 C26 1.385(5) . ?
C18 C19 1.494(4) . ?
C8 C7 1.367(4) . ?
C4 C3 1.358(5) . ?
C13 C14 1.384(4) . ?
C5 C6 1.357(6) . ?
C6 C7 1.389(5) . ?
C25 C26 1.380(5) . ?
C20 C19 1.483(5) . ?

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
C18 N1 C11 111.3(2) . . ?
C18 N1 C21 106.0(2) . . ?
C11 N1 C21 113.8(2) . . ?
C9 C10 C4 119.5(3) . . ?
C9 C10 C5 119.5(3) . . ?
C4 C10 C5 121.0(4) . . ?
O1 C2 C1 123.1(3) . . ?
O1 C2 C3 115.4(3) . . ?
C1 C2 C3 121.5(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C1 119.3(3) . . ?
C8 C9 C1 122.9(3) . . ?
C17 C12 C13 118.9(3) . . ?
C17 C12 C11 122.0(3) . . ?
C13 C12 C11 119.1(3) . . ?
N1 C11 C12 112.4(2) . . ?
N1 C11 C1 110.1(2) . . ?
C12 C11 C1 110.1(2) . . ?
C2 C1 C9 118.7(3) . . ?
C2 C1 C11 121.0(3) . . ?
C9 C1 C11 120.1(3) . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 C21 121.3(3) . . ?
C23 C22 C21 120.1(3) . . ?
C12 C17 C16 120.5(3) . . ?
N1 C21 C22 112.8(3) . . ?
N1 C21 C20 104.1(2) . . ?
C22 C21 C20 112.4(3) . . ?
C24 C23 C22 120.6(4) . . ?
C25 C24 C23 120.1(4) . . ?
C14 C15 C16 119.2(3) . . ?
C22 C27 C26 120.7(4) . . ?
N1 C18 C19 103.0(3) . . ?
C7 C8 C9 120.5(4) . . ?
C3 C4 C10 120.5(3) . . ?
C14 C13 C12 119.9(3) . . ?
C4 C3 C2 120.4(3) . . ?
C15 C16 C17 120.4(4) . . ?
C6 C5 C10 120.7(4) . . ?
C5 C6 C7 120.2(4) . . ?
C8 C7 C6 121.3(4) . . ?
C15 C14 C13 121.0(4) . . ?
C24 C25 C26 120.1(4) . . ?
C25 C26 C27 119.8(4) . . ?
C19 C20 C21 106.2(3) . . ?
C20 C19 C18 105.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
####################################################################### 
# 
# 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_ckj-sm3-81a_0m
_database_code_depnum_ccdc_archive 'CCDC 1506220'
_audit_update_record             
;
2016-09-25 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 N O'
_chemical_formula_sum            'C24 H25 N O'
_chemical_formula_weight         343.45

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 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8047(15)
_cell_length_b                   11.9575(13)
_cell_length_c                   16.3809(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.122(8)
_cell_angle_gamma                90.00
_cell_volume                     1905.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1191
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      17.77

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13044
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_sigmaI/netI    0.1584
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3370
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0100P)²+0.1000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1900
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.2865(3) 0.0454(2) 0.31065(13) 0.0860(10) Uani 1 1 d . . .
N1 N 0.0935(4) -0.0104(2) 0.21320(18) 0.0659(10) Uani 1 1 d . . .
C1 C 0.2562(5) 0.1303(3) 0.1761(2) 0.0654(12) Uani 1 1 d . . .
C2 C 0.3154(5) 0.1266(3) 0.2552(3) 0.0693(12) Uani 1 1 d . . .
C3 C 0.4082(5) 0.2085(4) 0.2884(2) 0.0860(14) Uani 1 1 d . . .
H3 H 0.4484 0.2036 0.3427 0.103 Uiso 1 1 calc R . .
C4 C 0.4389(5) 0.2950(3) 0.2404(3) 0.0869(14) Uani 1 1 d . . .
H4 H 0.5001 0.3496 0.2627 0.104 Uiso 1 1 calc R . .
C5 C 0.4094(5) 0.3960(3) 0.1076(3) 0.0880(15) Uani 1 1 d . . .
H5 H 0.4691 0.4519 0.1294 0.106 Uiso 1 1 calc R . .
C6 C 0.3514(6) 0.4028(3) 0.0291(3) 0.0973(16) Uani 1 1 d . . .
H6 H 0.3720 0.4629 -0.0033 0.117 Uiso 1 1 calc R . .
C7 C 0.2605(5) 0.3204(4) -0.0039(2) 0.0925(15) Uani 1 1 d . . .
H7 H 0.2203 0.3260 -0.0583 0.111 Uiso 1 1 calc R . .
C8 C 0.2300(5) 0.2316(3) 0.0427(2) 0.0764(13) Uani 1 1 d . . .
H8 H 0.1700 0.1769 0.0194 0.092 Uiso 1 1 calc R . .
C9 C 0.2872(5) 0.2212(3) 0.1250(2) 0.0663(12) Uani 1 1 d . . .
C10 C 0.3806(5) 0.3044(3) 0.1576(3) 0.0723(12) Uani 1 1 d . . .
C11 C 0.1542(5) 0.0393(2) 0.14478(19) 0.0637(11) Uani 1 1 d . . .
H11 H 0.0802 0.0743 0.1077 0.076 Uiso 1 1 calc R . .
C12 C 0.2184(6) -0.0529(3) 0.0968(2) 0.0673(12) Uani 1 1 d . . .
C13 C 0.3497(6) -0.0503(3) 0.0785(2) 0.0804(14) Uani 1 1 d . . .
H13 H 0.4055 0.0103 0.0957 0.097 Uiso 1 1 calc R . .
C14 C 0.4031(5) -0.1366(4) 0.0344(2) 0.0926(15) Uani 1 1 d . . .
H14 H 0.4931 -0.1336 0.0221 0.111 Uiso 1 1 calc R . .
C15 C 0.3198(8) -0.2257(4) 0.0097(2) 0.1007(17) Uani 1 1 d . . .
H15 H 0.3544 -0.2842 -0.0191 0.121 Uiso 1 1 calc R . .
C16 C 0.1871(8) -0.2299(3) 0.0266(3) 0.1134(19) Uani 1 1 d . . .
H16 H 0.1310 -0.2900 0.0086 0.136 Uiso 1 1 calc R . .
C17 C 0.1373(6) -0.1443(3) 0.0705(2) 0.1012(16) Uani 1 1 d . . .
H17 H 0.0473 -0.1477 0.0828 0.121 Uiso 1 1 calc R . .
C18 C 0.1926(5) -0.0441(3) 0.2782(2) 0.0765(14) Uani 1 1 d . . .
H18 H 0.2444 -0.1088 0.2618 0.092 Uiso 1 1 calc R . .
C19 C 0.1103(6) -0.0754(3) 0.3469(2) 0.0899(15) Uani 1 1 d . . .
H19A H 0.1611 -0.0589 0.4002 0.108 Uiso 1 1 calc R . .
H19B H 0.0868 -0.1542 0.3446 0.108 Uiso 1 1 calc R . .
C20 C -0.0182(6) -0.0032(3) 0.3313(2) 0.1093(18) Uani 1 1 d . . .
H20A H -0.0199 0.0515 0.3749 0.131 Uiso 1 1 calc R . .
H20B H -0.1000 -0.0492 0.3291 0.131 Uiso 1 1 calc R . .
C21 C -0.0128(6) 0.0556(3) 0.2487(2) 0.0767(14) Uani 1 1 d . . .
H21 H 0.0231 0.1313 0.2598 0.092 Uiso 1 1 calc R . .
C22 C -0.1458(7) 0.0647(4) 0.1925(3) 0.1025(16) Uani 1 1 d . . .
H22 H -0.1266 0.1105 0.1456 0.123 Uiso 1 1 calc R . .
C23 C -0.2528(7) 0.1284(4) 0.2347(3) 0.142(2) Uani 1 1 d . . .
H23A H -0.2125 0.1957 0.2588 0.214 Uiso 1 1 calc R . .
H23B H -0.2835 0.0824 0.2768 0.214 Uiso 1 1 calc R . .
H23C H -0.3296 0.1471 0.1948 0.214 Uiso 1 1 calc R . .
C24 C -0.2030(7) -0.0432(4) 0.1579(3) 0.171(3) Uani 1 1 d . . .
H24A H -0.2003 -0.0978 0.2010 0.256 Uiso 1 1 calc R . .
H24B H -0.1493 -0.0690 0.1165 0.256 Uiso 1 1 calc R . .
H24C H -0.2964 -0.0322 0.1338 0.256 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 C2 1.383(4) . ?
O1 C18 1.468(4) . ?
N1 C18 1.409(5) . ?
N1 C11 1.459(4) . ?
N1 C21 1.482(5) . ?
C1 C2 1.352(4) . ?
C1 C9 1.427(4) . ?
C1 C11 1.523(5) . ?
C2 C3 1.400(5) . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C10 1.409(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.342(5) . ?
C5 C10 1.418(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.411(5) . ?
C11 C12 1.534(5) . ?
C11 H11 0.9800 . ?
C12 C13 1.359(6) . ?
C12 C17 1.388(5) . ?
C13 C14 1.397(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.511(5) . ?
C18 H18 0.9800 . ?
C19 C20 1.523(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.530(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.504(6) . ?
C21 H21 0.9800 . ?
C22 C24 1.491(6) . ?
C22 C23 1.529(6) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C2 O1 C18 116.4(3) . . ?
C18 N1 C11 112.9(3) . . ?
C18 N1 C21 108.0(3) . . ?
C11 N1 C21 117.3(3) . . ?
C2 C1 C9 119.3(4) . . ?
C2 C1 C11 119.0(3) . . ?
C9 C1 C11 121.6(4) . . ?
C1 C2 O1 123.6(4) . . ?
C1 C2 C3 122.0(4) . . ?
O1 C2 C3 114.3(4) . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C10 121.7(4) . . ?
C3 C4 H4 119.1 . . ?
C10 C4 H4 119.1 . . ?
C6 C5 C10 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.3(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 117.7(4) . . ?
C8 C9 C1 123.0(4) . . ?
C10 C9 C1 119.3(4) . . ?
C4 C10 C9 118.4(4) . . ?
C4 C10 C5 122.1(4) . . ?
C9 C10 C5 119.5(4) . . ?
N1 C11 C1 110.2(3) . . ?
N1 C11 C12 109.4(2) . . ?
C1 C11 C12 113.1(3) . . ?
N1 C11 H11 108.0 . . ?
C1 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C13 C12 C17 118.1(4) . . ?
C13 C12 C11 123.9(4) . . ?
C17 C12 C11 118.0(4) . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 121.4(5) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
N1 C18 O1 114.1(3) . . ?
N1 C18 C19 104.6(4) . . ?
O1 C18 C19 106.2(3) . . ?
N1 C18 H18 110.6 . . ?
O1 C18 H18 110.6 . . ?
C19 C18 H18 110.6 . . ?
C18 C19 C20 104.0(3) . . ?
C18 C19 H19A 111.0 . . ?
C20 C19 H19A 111.0 . . ?
C18 C19 H19B 111.0 . . ?
C20 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C19 C20 C21 106.9(4) . . ?
C19 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
N1 C21 C22 113.4(3) . . ?
N1 C21 C20 101.9(3) . . ?
C22 C21 C20 116.9(4) . . ?
N1 C21 H21 108.1 . . ?
C22 C21 H21 108.1 . . ?
C20 C21 H21 108.1 . . ?
C24 C22 C21 115.3(4) . . ?
C24 C22 C23 110.8(5) . . ?
C21 C22 C23 110.6(4) . . ?
C24 C22 H22 106.5 . . ?
C21 C22 H22 106.5 . . ?
C23 C22 H22 106.5 . . ?
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 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C9 C1 C2 O1 176.5(3) . . . . ?
C11 C1 C2 O1 -1.4(5) . . . . ?
C9 C1 C2 C3 -1.0(5) . . . . ?
C11 C1 C2 C3 -178.9(4) . . . . ?
C18 O1 C2 C1 4.0(5) . . . . ?
C18 O1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
O1 C2 C3 C4 -177.0(3) . . . . ?
C2 C3 C4 C10 -0.5(6) . . . . ?
C10 C5 C6 C7 0.8(7) . . . . ?
C5 C6 C7 C8 -0.4(7) . . . . ?
C6 C7 C8 C9 0.8(6) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C7 C8 C9 C1 179.1(4) . . . . ?
C2 C1 C9 C8 -179.7(4) . . . . ?
C11 C1 C9 C8 -1.8(5) . . . . ?
C2 C1 C9 C10 0.9(5) . . . . ?
C11 C1 C9 C10 178.8(3) . . . . ?
C3 C4 C10 C9 0.4(6) . . . . ?
C3 C4 C10 C5 178.4(4) . . . . ?
C8 C9 C10 C4 180.0(3) . . . . ?
C1 C9 C10 C4 -0.6(5) . . . . ?
C8 C9 C10 C5 1.9(5) . . . . ?
C1 C9 C10 C5 -178.7(3) . . . . ?
C6 C5 C10 C4 -179.6(4) . . . . ?
C6 C5 C10 C9 -1.6(6) . . . . ?
C18 N1 C11 C1 -50.8(4) . . . . ?
C21 N1 C11 C1 75.7(4) . . . . ?
C18 N1 C11 C12 74.2(4) . . . . ?
C21 N1 C11 C12 -159.4(4) . . . . ?
C2 C1 C11 N1 24.1(5) . . . . ?
C9 C1 C11 N1 -153.8(3) . . . . ?
C2 C1 C11 C12 -98.7(4) . . . . ?
C9 C1 C11 C12 83.4(4) . . . . ?
N1 C11 C12 C13 -128.0(4) . . . . ?
C1 C11 C12 C13 -4.7(5) . . . . ?
N1 C11 C12 C17 52.2(4) . . . . ?
C1 C11 C12 C17 175.4(3) . . . . ?
C17 C12 C13 C14 0.0(5) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C15 C16 C17 C12 1.0(7) . . . . ?
C13 C12 C17 C16 -0.4(6) . . . . ?
C11 C12 C17 C16 179.4(3) . . . . ?
C11 N1 C18 O1 55.7(4) . . . . ?
C21 N1 C18 O1 -75.6(4) . . . . ?
C11 N1 C18 C19 171.3(2) . . . . ?
C21 N1 C18 C19 40.1(4) . . . . ?
C2 O1 C18 N1 -31.1(5) . . . . ?
C2 O1 C18 C19 -145.7(3) . . . . ?
N1 C18 C19 C20 -28.0(4) . . . . ?
O1 C18 C19 C20 92.9(4) . . . . ?
C18 C19 C20 C21 6.8(4) . . . . ?
C18 N1 C21 C22 -161.0(3) . . . . ?
C11 N1 C21 C22 70.2(5) . . . . ?
C18 N1 C21 C20 -34.6(4) . . . . ?
C11 N1 C21 C20 -163.4(3) . . . . ?
C19 C20 C21 N1 15.4(5) . . . . ?
C19 C20 C21 C22 139.5(4) . . . . ?
N1 C21 C22 C24 50.3(5) . . . . ?
C20 C21 C22 C24 -67.7(5) . . . . ?
N1 C21 C22 C23 177.0(3) . . . . ?
C20 C21 C22 C23 59.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044


_chemical_name_systematic        
(7aS,10R,12R)-10-isopropyl-12-phenyl-8,9,10,12-tetrahydro-7aH-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_ckj_3_07_ab
_database_code_depnum_ccdc_archive 'CCDC 1507198'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(7aS,11R,13R)-11-benzyl-13-phenyl-7a,8,9,10,11,13-hexahydronaphtho[1,2-e]pyrido[2,1-b][1,3]oxazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H27 N O'
_chemical_formula_sum            'C29 H27 N O'
_chemical_formula_weight         405.52

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'
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   P21/c

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

_cell_length_a                   7.9410(4)
_cell_length_b                   32.3062(15)
_cell_length_c                   17.2176(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.624(5)
_cell_angle_gamma                90.00
_cell_volume                     4395.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3905
_cell_measurement_theta_min      3.5580
_cell_measurement_theta_max      26.3120

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17711
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7750
_reflns_number_gt                4906
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0532P)²+1.2716P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7750
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.8311(2) 0.69505(6) 0.46600(10) 0.0496(5) Uani 1 1 d . . .
O2 O 0.6191(2) 0.42266(6) 0.07555(10) 0.0532(5) Uani 1 1 d . . .
N1 N 0.8300(2) 0.65612(6) 0.34642(11) 0.0359(5) Uani 1 1 d . . .
N2 N 0.6093(2) 0.46379(6) 0.19234(11) 0.0377(5) Uani 1 1 d . . .
C24 C 0.8536(3) 0.71030(8) 0.24765(13) 0.0334(6) Uani 1 1 d . . .
C1 C 1.0399(3) 0.71163(8) 0.37877(13) 0.0336(6) Uani 1 1 d . . .
C53 C 0.5806(3) 0.40966(8) 0.29148(14) 0.0354(6) Uani 1 1 d . . .
C9 C 1.1944(3) 0.73268(8) 0.36859(14) 0.0355(6) Uani 1 1 d . . .
C11 C 0.9475(3) 0.68587(8) 0.31431(13) 0.0350(6) Uani 1 1 d . . .
H11 H 1.0336 0.6694 0.2914 0.042 Uiso 1 1 calc R . .
C2 C 0.9783(3) 0.71398(8) 0.45026(14) 0.0384(6) Uani 1 1 d . . .
C38 C 0.2441(3) 0.38750(8) 0.16745(15) 0.0399(6) Uani 1 1 d . . .
C40 C 0.4905(3) 0.43405(8) 0.22387(14) 0.0367(6) Uani 1 1 d . . .
H40 H 0.4029 0.4506 0.2456 0.044 Uiso 1 1 calc R . .
C10 C 1.2805(3) 0.75485(8) 0.43167(15) 0.0391(6) Uani 1 1 d . . .
C30 C 0.4016(3) 0.40792(8) 0.15939(14) 0.0374(6) Uani 1 1 d . . .
C8 C 1.2662(3) 0.73280(8) 0.29610(15) 0.0411(6) Uani 1 1 d . . .
H8 H 1.2128 0.7183 0.2540 0.049 Uiso 1 1 calc R . .
C12 C 0.9095(3) 0.61752(8) 0.37991(14) 0.0399(6) Uani 1 1 d . . .
H12 H 0.9990 0.6249 0.4208 0.048 Uiso 1 1 calc R . .
C18 C 1.0808(3) 0.55450(8) 0.34628(15) 0.0426(6) Uani 1 1 d . . .
C39 C 0.1629(3) 0.36466(8) 0.10405(16) 0.0469(7) Uani 1 1 d . . .
C29 C 0.8540(3) 0.75295(8) 0.24377(15) 0.0408(6) Uani 1 1 d . . .
H29 H 0.9112 0.7681 0.2840 0.049 Uiso 1 1 calc R . .
C41 C 0.5277(3) 0.50081(8) 0.15406(14) 0.0415(6) Uani 1 1 d . . .
H41 H 0.4432 0.4918 0.1121 0.050 Uiso 1 1 calc R . .
C58 C 0.5773(3) 0.36689(8) 0.29619(16) 0.0444(7) Uani 1 1 d . . .
H58 H 0.5209 0.3518 0.2557 0.053 Uiso 1 1 calc R . .
C16 C 0.7296(3) 0.67838(8) 0.39768(15) 0.0411(6) Uani 1 1 d . . .
H16 H 0.6740 0.7015 0.3686 0.049 Uiso 1 1 calc R . .
C37 C 0.1660(3) 0.38858(8) 0.23807(16) 0.0450(7) Uani 1 1 d . . .
H37 H 0.2166 0.4034 0.2805 0.054 Uiso 1 1 calc R . .
C47 C 0.3540(3) 0.56482(8) 0.18131(15) 0.0449(7) Uani 1 1 d . . .
C54 C 0.6675(3) 0.43107(9) 0.35293(14) 0.0465(7) Uani 1 1 d . . .
H54 H 0.6714 0.4598 0.3513 0.056 Uiso 1 1 calc R . .
C45 C 0.7140(3) 0.44105(9) 0.14350(15) 0.0448(7) Uani 1 1 d . . .
H45 H 0.7696 0.4187 0.1748 0.054 Uiso 1 1 calc R . .
C31 C 0.4703(3) 0.40440(8) 0.08936(15) 0.0440(7) Uani 1 1 d . . .
C27 C 0.6841(3) 0.75156(10) 0.12043(15) 0.0504(7) Uani 1 1 d . . .
H27 H 0.6288 0.7653 0.0778 0.060 Uiso 1 1 calc R . .
C3 C 1.0655(4) 0.73506(9) 0.51400(15) 0.0499(7) Uani 1 1 d . . .
H3 H 1.0222 0.7354 0.5622 0.060 Uiso 1 1 calc R . .
C28 C 0.7694(3) 0.77357(9) 0.18022(16) 0.0492(7) Uani 1 1 d . . .
H28 H 0.7709 0.8023 0.1783 0.059 Uiso 1 1 calc R . .
C25 C 0.7658(3) 0.68858(9) 0.18721(15) 0.0493(7) Uani 1 1 d . . .
H25 H 0.7636 0.6598 0.1890 0.059 Uiso 1 1 calc R . .
C32 C 0.3883(4) 0.38213(9) 0.02589(16) 0.0522(7) Uani 1 1 d . . .
H32 H 0.4363 0.3808 -0.0212 0.063 Uiso 1 1 calc R . .
C5 C 1.4300(3) 0.77677(9) 0.41934(17) 0.0493(7) Uani 1 1 d . . .
H5 H 1.4853 0.7918 0.4603 0.059 Uiso 1 1 calc R . .
C26 C 0.6814(4) 0.70899(10) 0.12427(16) 0.0542(8) Uani 1 1 d . . .
H26 H 0.6225 0.6939 0.0844 0.065 Uiso 1 1 calc R . .
C4 C 1.2129(3) 0.75474(9) 0.50431(16) 0.0491(7) Uani 1 1 d . . .
H4 H 1.2705 0.7684 0.5464 0.059 Uiso 1 1 calc R . .
C42 C 0.6604(4) 0.52727(9) 0.11920(17) 0.0534(7) Uani 1 1 d . . .
H42A H 0.6037 0.5496 0.0893 0.064 Uiso 1 1 calc R . .
H42B H 0.7335 0.5396 0.1614 0.064 Uiso 1 1 calc R . .
C7 C 1.4125(3) 0.75384(9) 0.28722(17) 0.0486(7) Uani 1 1 d . . .
H7 H 1.4580 0.7532 0.2395 0.058 Uiso 1 1 calc R . .
C33 C 0.2394(4) 0.36268(9) 0.03376(17) 0.0556(8) Uani 1 1 d . . .
H33 H 0.1870 0.3478 -0.0080 0.067 Uiso 1 1 calc R . .
C34 C 0.0087(4) 0.34417(9) 0.1132(2) 0.0580(8) Uani 1 1 d . . .
H34 H -0.0452 0.3294 0.0716 0.070 Uiso 1 1 calc R . .
C19 C 1.2425(4) 0.55746(10) 0.38382(16) 0.0524(7) Uani 1 1 d . . .
H19 H 1.2934 0.5833 0.3909 0.063 Uiso 1 1 calc R . .
C46 C 0.4392(4) 0.52635(9) 0.21373(16) 0.0510(7) Uani 1 1 d . . .
H46A H 0.3554 0.5090 0.2352 0.061 Uiso 1 1 calc R . .
H46B H 0.5224 0.5340 0.2563 0.061 Uiso 1 1 calc R . .
C17 C 0.9873(4) 0.59283(9) 0.31643(15) 0.0499(7) Uani 1 1 d . . .
H17A H 0.8980 0.5848 0.2768 0.060 Uiso 1 1 calc R . .
H17B H 1.0650 0.6106 0.2918 0.060 Uiso 1 1 calc R . .
C6 C 1.4944(3) 0.77638(9) 0.34918(18) 0.0515(7) Uani 1 1 d . . .
H6 H 1.5926 0.7911 0.3423 0.062 Uiso 1 1 calc R . .
C48 C 0.4162(4) 0.60389(9) 0.19945(18) 0.0566(8) Uani 1 1 d . . .
H48 H 0.5159 0.6066 0.2323 0.068 Uiso 1 1 calc R . .
C15 C 0.5958(3) 0.65257(9) 0.43064(17) 0.0517(7) Uani 1 1 d . . .
H15A H 0.5124 0.6439 0.3888 0.062 Uiso 1 1 calc R . .
H15B H 0.5387 0.6690 0.4673 0.062 Uiso 1 1 calc R . .
C13 C 0.7769(4) 0.59142(9) 0.41566(17) 0.0532(7) Uani 1 1 d . . .
H13A H 0.6997 0.5801 0.3738 0.064 Uiso 1 1 calc R . .
H13B H 0.8332 0.5683 0.4433 0.064 Uiso 1 1 calc R . .
C55 C 0.7485(4) 0.41041(11) 0.41669(16) 0.0579(8) Uani 1 1 d . . .
H55 H 0.8075 0.4253 0.4569 0.069 Uiso 1 1 calc R . .
C23 C 1.0108(4) 0.51556(9) 0.33619(19) 0.0607(8) Uani 1 1 d . . .
H23 H 0.9030 0.5127 0.3103 0.073 Uiso 1 1 calc R . .
C14 C 0.6748(4) 0.61477(9) 0.47161(18) 0.0579(8) Uani 1 1 d . . .
H14A H 0.5869 0.5970 0.4885 0.069 Uiso 1 1 calc R . .
H14B H 0.7478 0.6232 0.5173 0.069 Uiso 1 1 calc R . .
C36 C 0.0165(3) 0.36807(9) 0.24460(19) 0.0562(8) Uani 1 1 d . . .
H36 H -0.0329 0.3691 0.2913 0.067 Uiso 1 1 calc R . .
C57 C 0.6564(4) 0.34630(10) 0.36015(17) 0.0580(8) Uani 1 1 d . . .
H57 H 0.6518 0.3176 0.3622 0.070 Uiso 1 1 calc R . .
C44 C 0.8496(3) 0.46680(10) 0.11114(18) 0.0570(8) Uani 1 1 d . . .
H44A H 0.9110 0.4501 0.0766 0.068 Uiso 1 1 calc R . .
H44B H 0.9293 0.4766 0.1535 0.068 Uiso 1 1 calc R . .
C56 C 0.7415(4) 0.36769(11) 0.42040(17) 0.0583(8) Uani 1 1 d . . .
H56 H 0.7940 0.3537 0.4633 0.070 Uiso 1 1 calc R . .
C49 C 0.3342(4) 0.63926(10) 0.1700(2) 0.0678(9) Uani 1 1 d . . .
H49 H 0.3793 0.6652 0.1827 0.081 Uiso 1 1 calc R . .
C35 C -0.0618(4) 0.34578(9) 0.1817(2) 0.0605(9) Uani 1 1 d . . .
H35 H -0.1628 0.3319 0.1869 0.073 Uiso 1 1 calc R . .
C21 C 1.2576(5) 0.48429(11) 0.4013(2) 0.0708(10) Uani 1 1 d . . .
H21 H 1.3166 0.4609 0.4200 0.085 Uiso 1 1 calc R . .
C52 C 0.2057(4) 0.56240(10) 0.13214(19) 0.0639(9) Uani 1 1 d . . .
H52 H 0.1605 0.5365 0.1185 0.077 Uiso 1 1 calc R . .
C43 C 0.7688(4) 0.50337(10) 0.06673(17) 0.0589(8) Uani 1 1 d . . .
H43A H 0.6993 0.4937 0.0208 0.071 Uiso 1 1 calc R . .
H43B H 0.8560 0.5213 0.0497 0.071 Uiso 1 1 calc R . .
C50 C 0.1867(5) 0.63581(11) 0.1222(2) 0.0731(10) Uani 1 1 d . . .
H50 H 0.1298 0.6594 0.1031 0.088 Uiso 1 1 calc R . .
C22 C 1.0975(5) 0.48079(10) 0.3637(2) 0.0775(11) Uani 1 1 d . . .
H22 H 1.0475 0.4549 0.3568 0.093 Uiso 1 1 calc R . .
C20 C 1.3287(4) 0.52258(11) 0.41074(18) 0.0662(9) Uani 1 1 d . . .
H20 H 1.4373 0.5252 0.4358 0.079 Uiso 1 1 calc R . .
C51 C 0.1237(4) 0.59745(12) 0.1030(2) 0.0785(11) Uani 1 1 d . . .
H51 H 0.0244 0.5950 0.0699 0.094 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 C2 1.370(3) . ?
O1 C16 1.462(3) . ?
O2 C31 1.363(3) . ?
O2 C45 1.455(3) . ?
N1 C16 1.439(3) . ?
N1 C11 1.484(3) . ?
N1 C12 1.488(3) . ?
N2 C45 1.441(3) . ?
N2 C41 1.484(3) . ?
N2 C40 1.486(3) . ?
C24 C29 1.379(3) . ?
C24 C25 1.385(3) . ?
C24 C11 1.526(3) . ?
C1 C2 1.371(3) . ?
C1 C9 1.428(3) . ?
C1 C11 1.518(3) . ?
C53 C58 1.385(4) . ?
C53 C54 1.389(3) . ?
C53 C40 1.525(3) . ?
C9 C10 1.419(3) . ?
C9 C8 1.422(3) . ?
C2 C3 1.414(4) . ?
C38 C37 1.419(4) . ?
C38 C39 1.419(4) . ?
C38 C30 1.433(3) . ?
C40 C30 1.513(3) . ?
C10 C4 1.408(4) . ?
C10 C5 1.416(4) . ?
C30 C31 1.376(3) . ?
C8 C7 1.367(3) . ?
C12 C13 1.525(3) . ?
C12 C17 1.532(3) . ?
C18 C23 1.379(4) . ?
C18 C19 1.383(4) . ?
C18 C17 1.508(4) . ?
C39 C33 1.408(4) . ?
C39 C34 1.414(4) . ?
C29 C28 1.395(4) . ?
C41 C42 1.525(4) . ?
C41 C46 1.540(3) . ?
C58 C57 1.384(4) . ?
C16 C15 1.505(3) . ?
C37 C36 1.373(4) . ?
C47 C48 1.380(4) . ?
C47 C52 1.383(4) . ?
C47 C46 1.497(4) . ?
C54 C55 1.388(4) . ?
C45 C44 1.510(4) . ?
C31 C32 1.413(4) . ?
C27 C28 1.374(4) . ?
C27 C26 1.377(4) . ?
C3 C4 1.356(4) . ?
C25 C26 1.385(4) . ?
C32 C33 1.358(4) . ?
C5 C6 1.357(4) . ?
C42 C43 1.518(4) . ?
C7 C6 1.398(4) . ?
C34 C35 1.355(4) . ?
C19 C20 1.375(4) . ?
C48 C49 1.386(4) . ?
C15 C14 1.515(4) . ?
C13 C14 1.519(4) . ?
C55 C56 1.383(4) . ?
C23 C22 1.377(4) . ?
C36 C35 1.394(4) . ?
C57 C56 1.369(4) . ?
C44 C43 1.515(4) . ?
C49 C50 1.369(5) . ?
C21 C20 1.363(5) . ?
C21 C22 1.373(5) . ?
C52 C51 1.377(4) . ?
C50 C51 1.365(5) . ?

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
C2 O1 C16 114.78(18) . . ?
C31 O2 C45 115.24(19) . . ?
C16 N1 C11 108.16(19) . . ?
C16 N1 C12 114.88(19) . . ?
C11 N1 C12 115.37(18) . . ?
C45 N2 C41 113.82(19) . . ?
C45 N2 C40 107.89(19) . . ?
C41 N2 C40 114.73(18) . . ?
C29 C24 C25 118.2(2) . . ?
C29 C24 C11 123.4(2) . . ?
C25 C24 C11 118.4(2) . . ?
C2 C1 C9 118.1(2) . . ?
C2 C1 C11 119.8(2) . . ?
C9 C1 C11 122.1(2) . . ?
C58 C53 C54 117.6(2) . . ?
C58 C53 C40 123.4(2) . . ?
C54 C53 C40 119.0(2) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 C1 120.1(2) . . ?
C8 C9 C1 122.1(2) . . ?
N1 C11 C1 111.07(18) . . ?
N1 C11 C24 109.67(18) . . ?
C1 C11 C24 115.6(2) . . ?
O1 C2 C1 122.7(2) . . ?
O1 C2 C3 115.1(2) . . ?
C1 C2 C3 122.2(2) . . ?
C37 C38 C39 117.9(2) . . ?
C37 C38 C30 122.1(2) . . ?
C39 C38 C30 120.0(2) . . ?
N2 C40 C30 111.08(19) . . ?
N2 C40 C53 110.22(18) . . ?
C30 C40 C53 115.0(2) . . ?
C4 C10 C5 122.2(2) . . ?
C4 C10 C9 118.8(2) . . ?
C5 C10 C9 119.0(2) . . ?
C31 C30 C38 118.1(2) . . ?
C31 C30 C40 119.5(2) . . ?
C38 C30 C40 122.3(2) . . ?
C7 C8 C9 121.2(2) . . ?
N1 C12 C13 109.6(2) . . ?
N1 C12 C17 110.2(2) . . ?
C13 C12 C17 110.1(2) . . ?
C23 C18 C19 117.8(3) . . ?
C23 C18 C17 121.8(3) . . ?
C19 C18 C17 120.4(3) . . ?
C33 C39 C34 121.7(3) . . ?
C33 C39 C38 118.9(2) . . ?
C34 C39 C38 119.4(3) . . ?
C24 C29 C28 120.8(3) . . ?
N2 C41 C42 109.8(2) . . ?
N2 C41 C46 110.1(2) . . ?
C42 C41 C46 109.9(2) . . ?
C57 C58 C53 121.1(3) . . ?
N1 C16 O1 112.51(19) . . ?
N1 C16 C15 114.1(2) . . ?
O1 C16 C15 104.7(2) . . ?
C36 C37 C38 120.8(3) . . ?
C48 C47 C52 117.0(3) . . ?
C48 C47 C46 122.4(3) . . ?
C52 C47 C46 120.5(3) . . ?
C55 C54 C53 121.3(3) . . ?
N2 C45 O2 113.2(2) . . ?
N2 C45 C44 114.1(2) . . ?
O2 C45 C44 105.1(2) . . ?
O2 C31 C30 122.8(2) . . ?
O2 C31 C32 115.3(2) . . ?
C30 C31 C32 121.9(3) . . ?
C28 C27 C26 119.3(3) . . ?
C4 C3 C2 119.6(2) . . ?
C27 C28 C29 120.3(3) . . ?
C26 C25 C24 121.1(3) . . ?
C33 C32 C31 119.9(3) . . ?
C6 C5 C10 121.6(3) . . ?
C27 C26 C25 120.3(3) . . ?
C3 C4 C10 121.2(2) . . ?
C43 C42 C41 113.8(2) . . ?
C8 C7 C6 120.7(2) . . ?
C32 C33 C39 121.2(3) . . ?
C35 C34 C39 121.0(3) . . ?
C20 C19 C18 120.6(3) . . ?
C47 C46 C41 114.5(2) . . ?
C18 C17 C12 113.8(2) . . ?
C5 C6 C7 119.8(2) . . ?
C47 C48 C49 121.7(3) . . ?
C16 C15 C14 110.3(2) . . ?
C14 C13 C12 114.4(2) . . ?
C56 C55 C54 119.9(3) . . ?
C22 C23 C18 121.2(3) . . ?
C15 C14 C13 109.1(2) . . ?
C37 C36 C35 120.6(3) . . ?
C56 C57 C58 120.8(3) . . ?
C45 C44 C43 109.5(2) . . ?
C57 C56 C55 119.2(3) . . ?
C50 C49 C48 119.8(3) . . ?
C34 C35 C36 120.3(3) . . ?
C20 C21 C22 119.0(3) . . ?
C51 C52 C47 121.4(3) . . ?
C44 C43 C42 109.5(2) . . ?
C51 C50 C49 119.4(3) . . ?
C21 C22 C23 120.2(3) . . ?
C21 C20 C19 121.1(3) . . ?
C50 C51 C52 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
