# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_cu_14jlv001_0m
_database_code_depnum_ccdc_archive 'CCDC 1431555'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N O'
_chemical_formula_weight         333.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.707(5)
_cell_length_b                   6.566(5)
_cell_length_c                   12.828(5)
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 102.872(5)
_cell_angle_gamma                90.000(0)
_cell_volume                     961.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9724
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      74.63

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36448
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         74.63
_reflns_number_total             3912
_reflns_number_gt                3866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0410P)²+0.1420P] 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   0.02(16)
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 0.07461(6) 0.66536(11) 0.57553(6) 0.02147(15) Uani 1 1 d . . .
N1 N -0.10619(7) 0.57884(12) 0.39995(6) 0.01684(17) Uani 1 1 d . . .
C8 C -0.28284(8) 0.75523(17) 0.15340(8) 0.0206(2) Uani 1 1 d . . .
H8 H -0.2763 0.8871 0.1805 0.025 Uiso 1 1 calc R . .
C7 C -0.24989(8) 0.60776(16) 0.22664(8) 0.0190(2) Uani 1 1 d . . .
C22 C 0.05977(9) 0.43767(17) 0.25171(8) 0.0243(2) Uani 1 1 d . . .
H005 H 0.0527 0.3312 0.2977 0.029 Uiso 1 1 calc R . .
C16 C -0.00132(8) 0.68657(15) 0.38112(8) 0.01737(19) Uani 1 1 d . . .
C17 C 0.03141(8) 0.63579(15) 0.27650(8) 0.0195(2) Uani 1 1 d . . .
C15 C -0.24816(9) 0.38322(16) 0.20284(8) 0.0234(2) Uani 1 1 d . . .
H15A H -0.3129 0.3503 0.1450 0.035 Uiso 1 1 calc R . .
H15B H -0.2544 0.3071 0.2652 0.035 Uiso 1 1 calc R . .
H15C H -0.1760 0.3492 0.1831 0.035 Uiso 1 1 calc R . .
C1 C -0.21888(8) 0.66924(15) 0.34363(8) 0.01766(19) Uani 1 1 d . . .
C3 C -0.28579(9) 0.64683(17) 0.51993(8) 0.0238(2) Uani 1 1 d . . .
H3 H -0.2345 0.5671 0.5692 0.029 Uiso 1 1 calc R . .
C2 C -0.31787(9) 0.60421(16) 0.40075(8) 0.0214(2) Uani 1 1 d . . .
C23 C 0.10064(8) 0.62968(15) 0.47426(8) 0.0200(2) Uani 1 1 d . . .
H17A H 0.1194 0.4868 0.4686 0.024 Uiso 1 1 calc R . .
H17B H 0.1692 0.7085 0.4689 0.024 Uiso 1 1 calc R . .
C11 C -0.44413(10) 0.8991(2) -0.12297(10) 0.0355(3) Uani 1 1 d . . .
H11 H -0.4895 1.0078 -0.1551 0.043 Uiso 1 1 calc R . .
C9 C -0.32776(8) 0.74038(18) 0.03658(8) 0.0235(2) Uani 1 1 d . . .
C4 C -0.33950(10) 0.8113(2) 0.54581(9) 0.0297(2) Uani 1 1 d . . .
H4 H -0.3287 0.8626 0.6149 0.036 Uiso 1 1 calc R . .
C14 C -0.30603(10) 0.5781(2) -0.02675(9) 0.0295(2) Uani 1 1 d . . .
H14 H -0.2586 0.4710 0.0045 0.035 Uiso 1 1 calc R . .
C18 C 0.04147(9) 0.79200(17) 0.20570(9) 0.0256(2) Uani 1 1 d . . .
H19 H 0.0223 0.9245 0.2209 0.031 Uiso 1 1 calc R . .
C19 C 0.07985(10) 0.7527(2) 0.11255(9) 0.0331(3) Uani 1 1 d . . .
H20 H 0.0859 0.8584 0.0658 0.040 Uiso 1 1 calc R . .
C5 C -0.41956(11) 0.9040(2) 0.45027(10) 0.0354(3) Uani 1 1 d . . .
H5A H -0.3866 1.0284 0.4287 0.043 Uiso 1 1 calc R . .
H5B H -0.4958 0.9335 0.4646 0.043 Uiso 1 1 calc R . .
C20 C 0.10900(10) 0.5560(2) 0.08942(9) 0.0343(3) Uani 1 1 d . . .
H020 H 0.1355 0.5296 0.0276 0.041 Uiso 1 1 calc R . .
C10 C -0.39655(9) 0.90223(19) -0.01381(9) 0.0280(2) Uani 1 1 d . . .
H10 H -0.4105 1.0134 0.0265 0.034 Uiso 1 1 calc R . .
C21 C 0.09852(10) 0.3985(2) 0.15869(9) 0.0313(2) Uani 1 1 d . . .
H022 H 0.1175 0.2661 0.1429 0.038 Uiso 1 1 calc R . .
C6 C -0.42828(9) 0.73761(19) 0.36437(8) 0.0265(2) Uani 1 1 d . . .
H6A H -0.4299 0.7978 0.2950 0.032 Uiso 1 1 calc R . .
H6B H -0.4987 0.6571 0.3596 0.032 Uiso 1 1 calc R . .
C12 C -0.42442(10) 0.7354(2) -0.18402(9) 0.0382(3) Uani 1 1 d . . .
H12 H -0.4578 0.7326 -0.2569 0.046 Uiso 1 1 calc R . .
C13 C -0.35483(11) 0.5751(2) -0.13653(9) 0.0364(3) Uani 1 1 d . . .
H13 H -0.3406 0.4655 -0.1778 0.044 Uiso 1 1 calc R . .
H16 H -0.0136(10) 0.8338(18) 0.3819(9) 0.011(3) Uiso 1 1 d . . .
H1 H -0.2142(11) 0.825(2) 0.3473(9) 0.018(3) Uiso 1 1 d . . .
H2 H -0.3361(11) 0.462(2) 0.3849(10) 0.024(3) Uiso 1 1 d . . .
H1N H -0.1014(11) 0.590(2) 0.4729(11) 0.027(3) Uiso 1 1 d . . .
H1O H 0.0869(14) 0.786(3) 0.5924(12) 0.039(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.4183(13) . ?
N1 C1 1.4799(13) . ?
N1 C16 1.4826(13) . ?
C8 C7 1.3445(16) . ?
C8 C9 1.4767(15) . ?
C7 C15 1.5067(18) . ?
C7 C1 1.5180(14) . ?
C22 C21 1.3918(16) . ?
C22 C17 1.3966(17) . ?
C16 C17 1.5128(14) . ?
C16 C23 1.5352(13) . ?
C17 C18 1.3922(16) . ?
C1 C2 1.5622(14) . ?
C3 C4 1.3284(18) . ?
C3 C2 1.5168(15) . ?
C2 C6 1.5450(16) . ?
C11 C12 1.379(2) . ?
C11 C10 1.3871(17) . ?
C9 C14 1.3969(18) . ?
C9 C10 1.4013(17) . ?
C4 C5 1.4963(18) . ?
C14 C13 1.3970(16) . ?
C18 C19 1.3913(16) . ?
C19 C20 1.385(2) . ?
C5 C6 1.5387(17) . ?
C20 C21 1.387(2) . ?
C12 C13 1.386(2) . ?

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 C16 114.18(8) . . ?
C7 C8 C9 130.05(11) . . ?
C8 C7 C15 125.30(10) . . ?
C8 C7 C1 117.88(10) . . ?
C15 C7 C1 116.71(9) . . ?
C21 C22 C17 120.46(10) . . ?
N1 C16 C17 114.96(8) . . ?
N1 C16 C23 106.59(8) . . ?
C17 C16 C23 109.28(8) . . ?
C18 C17 C22 118.60(10) . . ?
C18 C17 C16 119.42(10) . . ?
C22 C17 C16 121.83(9) . . ?
N1 C1 C7 111.52(8) . . ?
N1 C1 C2 109.58(8) . . ?
C7 C1 C2 110.61(8) . . ?
C4 C3 C2 112.16(10) . . ?
C3 C2 C6 101.68(8) . . ?
C3 C2 C1 112.29(8) . . ?
C6 C2 C1 111.19(9) . . ?
O1 C23 C16 112.59(8) . . ?
C12 C11 C10 120.31(12) . . ?
C14 C9 C10 118.06(10) . . ?
C14 C9 C8 124.80(10) . . ?
C10 C9 C8 117.14(11) . . ?
C3 C4 C5 111.77(10) . . ?
C9 C14 C13 120.70(12) . . ?
C19 C18 C17 120.92(11) . . ?
C20 C19 C18 119.96(11) . . ?
C4 C5 C6 103.14(11) . . ?
C19 C20 C21 119.81(11) . . ?
C11 C10 C9 120.97(12) . . ?
C20 C21 C22 120.24(12) . . ?
C5 C6 C2 105.58(9) . . ?
C11 C12 C13 119.89(11) . . ?
C12 C13 C14 120.04(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        74.63
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_cu_14jlv002_0m
_database_code_depnum_ccdc_archive 'CCDC 1431556'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N O2'
_chemical_formula_weight         323.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.585(5)
_cell_length_b                   6.810(5)
_cell_length_c                   13.050(5)
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 109.415(5)
_cell_angle_gamma                90.000(0)
_cell_volume                     887.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9781
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      74.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32896
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         74.62
_reflns_number_total             3628
_reflns_number_gt                3527
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0386P)²+0.1390P] 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   -0.05(14)
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 0.40152(8) 0.23806(12) -0.08615(6) 0.01919(16) Uani 1 1 d . . .
O2 O 0.87059(9) 0.08282(14) 0.62370(6) 0.0296(2) Uani 1 1 d . . .
N1 N 0.61075(9) 0.14774(12) 0.10536(7) 0.01547(18) Uani 1 1 d . . .
C16 C 0.43794(11) 0.34843(18) 0.28028(9) 0.0230(2) Uani 1 1 d . . .
H16 H 0.4489 0.4788 0.2637 0.028 Uiso 1 1 calc R . .
C8 C 0.81021(11) 0.35063(16) 0.36612(9) 0.0200(2) Uani 1 1 d . . .
H8 H 0.8130 0.4773 0.3403 0.024 Uiso 1 1 calc R . .
C3 C 0.84673(11) 0.20243(17) 0.02073(9) 0.0218(2) Uani 1 1 d . . .
H3 H 0.7688 0.2026 -0.0393 0.026 Uiso 1 1 calc R . .
C7 C 0.77040(10) 0.19756(16) 0.29242(8) 0.0170(2) Uani 1 1 d . . .
C15 C 0.45744(10) 0.20017(16) 0.21414(8) 0.0175(2) Uani 1 1 d . . .
C14 C 0.49190(10) 0.25278(15) 0.11344(8) 0.0159(2) Uani 1 1 d . . .
C21 C 0.37334(10) 0.20175(16) 0.01125(8) 0.0178(2) Uani 1 1 d . . .
H01A H 0.3508 0.0642 0.0139 0.021 Uiso 1 1 calc R . .
H01B H 0.2961 0.2788 0.0107 0.021 Uiso 1 1 calc R . .
C9 C 0.84632(11) 0.32007(18) 0.47831(9) 0.0222(2) Uani 1 1 d . . .
H9 H 0.8740 0.4245 0.5266 0.027 Uiso 1 1 calc R . .
C2 C 0.85287(11) 0.14778(16) 0.13524(9) 0.0180(2) Uani 1 1 d . . .
C20 C 0.44005(11) 0.00561(17) 0.23992(9) 0.0221(2) Uani 1 1 d . . .
H20 H 0.4513 -0.0952 0.1957 0.027 Uiso 1 1 calc R . .
C17 C 0.40203(12) 0.3042(2) 0.37121(10) 0.0291(3) Uani 1 1 d . . .
H17 H 0.3882 0.4049 0.4145 0.035 Uiso 1 1 calc R . .
C1 C 0.74040(10) 0.23406(16) 0.17220(8) 0.0163(2) Uani 1 1 d . . .
C19 C 0.40593(12) -0.0385(2) 0.33142(10) 0.0280(3) Uani 1 1 d . . .
H19 H 0.3958 -0.1686 0.3488 0.034 Uiso 1 1 calc R . .
C4 C 0.96761(13) 0.2501(2) 0.01753(10) 0.0292(3) Uani 1 1 d . . .
H4 H 0.9843 0.2849 -0.0457 0.035 Uiso 1 1 calc R . .
C11 C 0.76649(11) 0.00783(16) 0.33288(9) 0.0196(2) Uani 1 1 d . . .
H11 H 0.7408 -0.0973 0.2849 0.024 Uiso 1 1 calc R . .
C12 C 0.84013(11) 0.13152(18) 0.51609(9) 0.0217(2) Uani 1 1 d . . .
C5 C 1.07312(11) 0.2412(2) 0.12718(9) 0.0262(2) Uani 1 1 d . . .
H5A H 1.1283 0.3584 0.1414 0.031 Uiso 1 1 calc R . .
H5B H 1.1300 0.1269 0.1337 0.031 Uiso 1 1 calc R . .
C10 C 0.80044(12) -0.02480(17) 0.44335(9) 0.0225(2) Uani 1 1 d . . .
H10 H 0.7968 -0.1512 0.4692 0.027 Uiso 1 1 calc R . .
C18 C 0.38702(12) 0.1115(2) 0.39700(10) 0.0301(3) Uani 1 1 d . . .
H18 H 0.3643 0.0819 0.4582 0.036 Uiso 1 1 calc R . .
C6 C 0.99179(11) 0.22719(19) 0.20387(9) 0.0231(2) Uani 1 1 d . . .
H6A H 0.9834 0.3554 0.2333 0.028 Uiso 1 1 calc R . .
H6B H 1.0347 0.1388 0.2636 0.028 Uiso 1 1 calc R . .
C13 C 0.92276(14) 0.2341(2) 0.70100(9) 0.0324(3) Uani 1 1 d . . .
H13A H 1.0036 0.2848 0.6929 0.049 Uiso 1 1 calc R . .
H13B H 0.9419 0.1822 0.7730 0.049 Uiso 1 1 calc R . .
H13C H 0.8581 0.3379 0.6894 0.049 Uiso 1 1 calc R . .
H1 H 0.7375(13) 0.381(2) 0.1606(10) 0.015(3) Uiso 1 1 d . . .
H14 H 0.5080(13) 0.3924(19) 0.1154(10) 0.015(3) Uiso 1 1 d . . .
H1N H 0.6062(13) 0.1611(19) 0.0362(11) 0.017(3) Uiso 1 1 d . . .
H2 H 0.8468(14) 0.002(2) 0.1390(10) 0.022(3) Uiso 1 1 d . . .
H1O H 0.3951(15) 0.359(2) -0.0987(11) 0.025(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.4205(13) . ?
O2 C12 1.3730(14) . ?
O2 C13 1.4192(17) . ?
N1 C14 1.4811(15) . ?
N1 C1 1.4812(14) . ?
C16 C15 1.3876(17) . ?
C16 C17 1.3940(17) . ?
C8 C7 1.3855(16) . ?
C8 C9 1.4003(16) . ?
C3 C4 1.3340(18) . ?
C3 C2 1.5203(15) . ?
C7 C11 1.4016(17) . ?
C7 C1 1.5142(15) . ?
C15 C20 1.3942(18) . ?
C15 C14 1.5189(15) . ?
C14 C21 1.5367(14) . ?
C9 C12 1.3848(19) . ?
C2 C1 1.5417(15) . ?
C2 C6 1.5431(16) . ?
C20 C19 1.3903(15) . ?
C17 C18 1.377(2) . ?
C19 C18 1.389(2) . ?
C4 C5 1.4953(17) . ?
C11 C10 1.3829(16) . ?
C12 C10 1.3949(18) . ?
C5 C6 1.5246(15) . ?

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
C12 O2 C13 117.08(10) . . ?
C14 N1 C1 114.15(9) . . ?
C15 C16 C17 120.76(12) . . ?
C7 C8 C9 121.89(11) . . ?
C4 C3 C2 111.24(10) . . ?
C8 C7 C11 118.18(10) . . ?
C8 C7 C1 120.42(10) . . ?
C11 C7 C1 121.29(9) . . ?
C16 C15 C20 118.85(11) . . ?
C16 C15 C14 119.65(10) . . ?
C20 C15 C14 121.46(9) . . ?
N1 C14 C15 113.68(9) . . ?
N1 C14 C21 107.28(9) . . ?
C15 C14 C21 109.62(9) . . ?
O1 C21 C14 112.54(9) . . ?
C12 C9 C8 118.77(10) . . ?
C3 C2 C1 115.41(9) . . ?
C3 C2 C6 101.88(9) . . ?
C1 C2 C6 111.77(9) . . ?
C19 C20 C15 120.35(11) . . ?
C18 C17 C16 120.01(11) . . ?
N1 C1 C7 112.28(8) . . ?
N1 C1 C2 108.98(9) . . ?
C7 C1 C2 110.11(8) . . ?
C18 C19 C20 120.13(12) . . ?
C3 C4 C5 112.29(10) . . ?
C10 C11 C7 120.72(10) . . ?
O2 C12 C9 124.43(10) . . ?
O2 C12 C10 115.27(11) . . ?
C9 C12 C10 120.30(10) . . ?
C4 C5 C6 103.04(10) . . ?
C11 C10 C12 120.13(11) . . ?
C17 C18 C19 119.89(11) . . ?
C5 C6 C2 106.14(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        74.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
