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

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

data_ch17812
_database_code_depnum_ccdc_archive 'CCDC 1457405'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N O3'
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.5517(18)
_cell_length_b                   11.006(4)
_cell_length_c                   24.121(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1473.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1622
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.08

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9139
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.14
_reflns_number_total             2609
_reflns_number_gt                1853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_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)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_number_reflns         2609
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.2392(6) 0.1513(3) 0.19351(15) 0.0299(9) Uani 1 1 d . . .
C2 C 0.1086(6) 0.2338(3) 0.15652(15) 0.0340(9) Uani 1 1 d . . .
H2 H -0.0289 0.2756 0.1701 0.041 Uiso 1 1 calc R . .
C3 C 0.1776(6) 0.2516(3) 0.10440(15) 0.0310(9) Uani 1 1 d . . .
H3 H 0.0848 0.3040 0.0815 0.037 Uiso 1 1 calc R . .
C4 C 0.3931(6) 0.1929(3) 0.08088(14) 0.0248(8) Uani 1 1 d . . .
C5 C 0.5238(6) 0.1059(3) 0.11609(13) 0.0236(8) Uani 1 1 d . . .
C6 C 0.4480(6) 0.0833(3) 0.17077(14) 0.0270(8) Uani 1 1 d . . .
C7 C 0.5658(6) -0.0036(3) 0.20391(14) 0.0263(8) Uani 1 1 d . . .
C8 C 0.5025(7) -0.0261(3) 0.26350(15) 0.0352(9) Uani 1 1 d . . .
C9 C 0.6178(7) 0.0593(4) 0.30372(14) 0.0525(12) Uani 1 1 d . . .
H9A H 0.5674 0.0384 0.3415 0.079 Uiso 1 1 calc R . .
H9B H 0.5681 0.1427 0.2952 0.079 Uiso 1 1 calc R . .
H9C H 0.7934 0.0528 0.3008 0.079 Uiso 1 1 calc R . .
C10 C 0.7595(6) -0.0687(3) 0.18280(13) 0.0277(9) Uani 1 1 d . . .
H10 H 0.8369 -0.1284 0.2050 0.033 Uiso 1 1 calc R . .
C11 C 0.8392(6) -0.0466(3) 0.12967(12) 0.0223(8) Uani 1 1 d . . .
C12 C 0.7239(6) 0.0415(3) 0.09614(12) 0.0226(8) Uani 1 1 d . . .
C13 C 1.0309(5) -0.0352(3) 0.04581(13) 0.0221(8) Uani 1 1 d . . .
C14 C 1.0341(6) -0.0951(3) 0.09701(13) 0.0231(8) Uani 1 1 d . . .
C15 C 1.2130(6) -0.1810(3) 0.10851(14) 0.0278(9) Uani 1 1 d . . .
H15 H 1.2199 -0.2210 0.1434 0.033 Uiso 1 1 calc R . .
C16 C 1.3780(6) -0.2056(3) 0.06771(14) 0.0290(9) Uani 1 1 d . . .
H16 H 1.5006 -0.2640 0.0744 0.035 Uiso 1 1 calc R . .
C17 C 1.3692(6) -0.1460(3) 0.01643(14) 0.0268(8) Uani 1 1 d . . .
H17 H 1.4854 -0.1664 -0.0109 0.032 Uiso 1 1 calc R . .
C18 C 1.1981(6) -0.0587(3) 0.00395(13) 0.0234(8) Uani 1 1 d . . .
C19 C 1.1882(6) 0.0083(3) -0.05071(12) 0.0280(8) Uani 1 1 d . . .
H19A H 1.0234 0.0003 -0.0660 0.034 Uiso 1 1 calc R . .
H19B H 1.2165 0.0957 -0.0434 0.034 Uiso 1 1 calc R . .
C20 C 1.3644(6) -0.0331(3) -0.09422(14) 0.0341(9) Uani 1 1 d . . .
N1 N 0.8376(4) 0.0477(2) 0.04575(10) 0.0221(6) Uani 1 1 d . . .
H1' H 0.8290 0.1178 0.0221 0.026 Uiso 1 1 d R . .
O1 O 0.1746(5) 0.1384(2) 0.24152(10) 0.0447(7) Uani 1 1 d . . .
O2 O 0.4602(4) 0.2171(2) 0.03364(9) 0.0303(6) Uani 1 1 d . . .
O3 O 0.3889(6) -0.1150(3) 0.27741(11) 0.0589(9) Uani 1 1 d . . .
H20A H 1.3494 -0.1212 -0.1078 0.071 Uiso 1 1 d R . .
H20B H 1.3740 0.0074 -0.1287 0.071 Uiso 1 1 d R . .
H20C H 1.5169 -0.0425 -0.0831 0.071 Uiso 1 1 d 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
C1 O1 1.220(4) . ?
C1 C2 1.465(4) . ?
C1 C6 1.485(5) . ?
C2 C3 1.329(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.473(5) . ?
C3 H3 0.9500 . ?
C4 O2 1.228(4) . ?
C4 C5 1.472(4) . ?
C5 C12 1.403(4) . ?
C5 C6 1.407(4) . ?
C6 C7 1.408(5) . ?
C7 C10 1.389(5) . ?
C7 C8 1.500(5) . ?
C8 O3 1.211(4) . ?
C8 C9 1.495(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(4) . ?
C11 C14 1.441(4) . ?
C12 N1 1.371(4) . ?
C13 C18 1.396(4) . ?
C13 C14 1.400(4) . ?
C13 N1 1.408(4) . ?
C14 C15 1.400(5) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.512(4) . ?
C19 C20 1.505(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 1.0272 . ?
C20 H20B 0.9454 . ?
C20 H20C 0.8941 . ?
N1 H1' 0.9605 . ?

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
O1 C1 C2 120.3(3) . . ?
O1 C1 C6 121.4(3) . . ?
C2 C1 C6 118.3(3) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 122.3(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
O2 C4 C5 121.8(3) . . ?
O2 C4 C3 120.6(3) . . ?
C5 C4 C3 117.6(3) . . ?
C12 C5 C6 118.0(3) . . ?
C12 C5 C4 121.4(3) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 C1 119.4(3) . . ?
C7 C6 C1 119.7(3) . . ?
C10 C7 C6 120.1(3) . . ?
C10 C7 C8 116.6(3) . . ?
C6 C7 C8 123.2(3) . . ?
O3 C8 C9 123.4(4) . . ?
O3 C8 C7 121.4(3) . . ?
C9 C8 C7 114.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C7 C10 H10 120.1 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 C14 133.2(3) . . ?
C12 C11 C14 106.3(3) . . ?
N1 C12 C5 130.1(3) . . ?
N1 C12 C11 109.4(3) . . ?
C5 C12 C11 120.5(3) . . ?
C18 C13 C14 122.8(3) . . ?
C18 C13 N1 128.8(3) . . ?
C14 C13 N1 108.4(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 C11 132.5(3) . . ?
C13 C14 C11 107.4(3) . . ?
C16 C15 C14 117.7(3) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 122.7(3) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C13 115.4(3) . . ?
C17 C18 C19 123.6(3) . . ?
C13 C18 C19 121.0(3) . . ?
C20 C19 C18 115.9(3) . . ?
C20 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C19 C20 H20A 117.1 . . ?
C19 C20 H20B 120.5 . . ?
H20A C20 H20B 99.7 . . ?
C19 C20 H20C 116.2 . . ?
H20A C20 H20C 93.6 . . ?
H20B C20 H20C 105.4 . . ?
C12 N1 C13 108.5(2) . . ?
C12 N1 H1' 122.9 . . ?
C13 N1 H1' 124.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_ch17812a
_database_code_depnum_ccdc_archive 'CCDC 1457406'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N O2'
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41

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                   37.27(2)
_cell_length_b                   7.992(5)
_cell_length_c                   12.774(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.797(12)
_cell_angle_gamma                90.00
_cell_volume                     3803(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    778
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.17

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8320
_diffrn_reflns_av_R_equivalents  0.1911
_diffrn_reflns_av_sigmaI/netI    0.3117
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3210
_reflns_number_gt                1132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_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)+(0.0651P)²+14.0743P] 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         3210
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2953
_refine_ls_R_factor_gt           0.1225
_refine_ls_wR_factor_ref         0.2624
_refine_ls_wR_factor_gt          0.1931
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.96364(19) 0.0764(11) 1.1015(6) 0.036(2) Uani 1 1 d . . .
C2 C 1.00108(19) 0.1444(11) 1.1065(6) 0.040(2) Uani 1 1 d . . .
H2 H 1.0169 0.1111 1.1625 0.048 Uiso 1 1 calc R . .
C3 C 1.01291(19) 0.2505(11) 1.0347(6) 0.040(2) Uani 1 1 d . . .
H3 H 1.0368 0.2916 1.0416 0.049 Uiso 1 1 calc R . .
C4 C 0.99000(19) 0.3062(11) 0.9446(6) 0.037(2) Uani 1 1 d . . .
C5 C 0.95370(17) 0.2362(10) 0.9351(6) 0.029(2) Uani 1 1 d . . .
C6 C 0.94030(18) 0.1258(11) 1.0097(6) 0.033(2) Uani 1 1 d . . .
C7 C 0.90657(18) 0.0533(11) 0.9975(6) 0.034(2) Uani 1 1 d . . .
H7 H 0.8985 -0.0215 1.0496 0.041 Uiso 1 1 calc R . .
C8 C 0.88426(18) 0.0880(10) 0.9104(6) 0.034(2) Uani 1 1 d . . .
C9 C 0.84946(19) -0.0046(11) 0.8896(6) 0.038(2) Uani 1 1 d . . .
C10 C 0.8500(2) -0.1510(12) 0.8266(6) 0.041(2) Uani 1 1 d . . .
C11 C 0.8847(2) -0.2124(11) 0.7825(6) 0.058(3) Uani 1 1 d . . .
H11A H 0.9043 -0.1368 0.8041 0.087 Uiso 1 1 calc R . .
H11B H 0.8825 -0.2149 0.7058 0.087 Uiso 1 1 calc R . .
H11C H 0.8899 -0.3252 0.8088 0.087 Uiso 1 1 calc R . .
C12 C 0.8179(2) -0.2355(12) 0.8061(6) 0.049(2) Uani 1 1 d . . .
H12 H 0.8181 -0.3328 0.7634 0.059 Uiso 1 1 calc R . .
C13 C 0.7857(2) -0.1824(13) 0.8457(7) 0.049(3) Uani 1 1 d . . .
C14 C 0.7510(2) -0.2774(14) 0.8203(7) 0.090(4) Uani 1 1 d . . .
H14A H 0.7310 -0.2228 0.8550 0.135 Uiso 1 1 calc R . .
H14B H 0.7533 -0.3929 0.8453 0.135 Uiso 1 1 calc R . .
H14C H 0.7463 -0.2774 0.7444 0.135 Uiso 1 1 calc R . .
C15 C 0.7856(2) -0.0400(13) 0.9069(7) 0.054(3) Uani 1 1 d . . .
H15 H 0.7636 -0.0023 0.9340 0.064 Uiso 1 1 calc R . .
C16 C 0.81722(19) 0.0512(12) 0.9303(6) 0.042(2) Uani 1 1 d . . .
C17 C 0.8157(2) 0.2073(12) 0.9977(7) 0.068(3) Uani 1 1 d . . .
H17A H 0.8398 0.2550 1.0064 0.102 Uiso 1 1 calc R . .
H17B H 0.8066 0.1782 1.0665 0.102 Uiso 1 1 calc R . .
H17C H 0.7997 0.2895 0.9637 0.102 Uiso 1 1 calc R . .
C18 C 0.89629(18) 0.2028(11) 0.8365(6) 0.035(2) Uani 1 1 d . . .
C19 C 0.93123(17) 0.2773(10) 0.8496(6) 0.031(2) Uani 1 1 d . . .
C20 C 0.90804(18) 0.3663(11) 0.6926(6) 0.038(2) Uani 1 1 d . . .
C21 C 0.88197(17) 0.2654(10) 0.7361(6) 0.033(2) Uani 1 1 d . . .
C22 C 0.84929(19) 0.2404(11) 0.6781(6) 0.042(2) Uani 1 1 d . . .
H22 H 0.8308 0.1719 0.7046 0.051 Uiso 1 1 calc R . .
C23 C 0.8452(2) 0.3187(11) 0.5821(6) 0.046(3) Uani 1 1 d . . .
H23 H 0.8234 0.3048 0.5423 0.055 Uiso 1 1 calc R . .
C24 C 0.8724(2) 0.4177(11) 0.5424(6) 0.046(2) Uani 1 1 d . . .
H24 H 0.8686 0.4692 0.4759 0.055 Uiso 1 1 calc R . .
C25 C 0.9041(2) 0.4432(11) 0.5957(6) 0.038(2) Uani 1 1 d . . .
H25 H 0.9226 0.5100 0.5678 0.045 Uiso 1 1 calc R . .
N1 N 0.93729(15) 0.3749(8) 0.7629(5) 0.0363(18) Uani 1 1 d . . .
H1 H 0.9568 0.4340 0.7534 0.044 Uiso 1 1 calc R . .
O1 O 0.95346(13) -0.0140(7) 1.1723(4) 0.0475(17) Uani 1 1 d . . .
O2 O 1.00216(12) 0.4069(7) 0.8805(4) 0.0388(15) 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
C1 O1 1.227(8) . ?
C1 C6 1.491(9) . ?
C1 C2 1.497(10) . ?
C2 C3 1.335(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.480(10) . ?
C3 H3 0.9500 . ?
C4 O2 1.244(8) . ?
C4 C5 1.465(9) . ?
C5 C19 1.394(9) . ?
C5 C6 1.402(9) . ?
C6 C7 1.389(9) . ?
C7 C8 1.396(9) . ?
C7 H7 0.9500 . ?
C8 C18 1.400(10) . ?
C8 C9 1.510(10) . ?
C9 C16 1.397(9) . ?
C9 C10 1.420(11) . ?
C10 C12 1.394(10) . ?
C10 C11 1.509(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.384(10) . ?
C12 H12 0.9500 . ?
C13 C15 1.381(11) . ?
C13 C14 1.526(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.410(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.518(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.437(9) . ?
C18 C21 1.462(9) . ?
C19 N1 1.379(9) . ?
C20 C25 1.386(10) . ?
C20 N1 1.392(8) . ?
C20 C21 1.391(10) . ?
C21 C22 1.420(9) . ?
C22 C23 1.382(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.363(9) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 H1 0.8800 . ?

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
O1 C1 C6 123.3(7) . . ?
O1 C1 C2 119.5(7) . . ?
C6 C1 C2 117.2(7) . . ?
C3 C2 C1 121.9(7) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 122.1(7) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O2 C4 C5 123.2(7) . . ?
O2 C4 C3 119.5(7) . . ?
C5 C4 C3 117.3(7) . . ?
C19 C5 C6 117.6(7) . . ?
C19 C5 C4 120.3(7) . . ?
C6 C5 C4 122.1(7) . . ?
C7 C6 C5 121.8(7) . . ?
C7 C6 C1 118.8(7) . . ?
C5 C6 C1 119.3(7) . . ?
C6 C7 C8 121.4(8) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C18 118.2(7) . . ?
C7 C8 C9 122.0(7) . . ?
C18 C8 C9 119.6(7) . . ?
C16 C9 C10 120.2(7) . . ?
C16 C9 C8 121.5(8) . . ?
C10 C9 C8 118.3(7) . . ?
C12 C10 C9 118.5(8) . . ?
C12 C10 C11 120.9(8) . . ?
C9 C10 C11 120.6(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 122.2(9) . . ?
C13 C12 H12 118.9 . . ?
C10 C12 H12 118.9 . . ?
C12 C13 C15 118.5(8) . . ?
C12 C13 C14 120.6(9) . . ?
C15 C13 C14 120.9(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 122.0(8) . . ?
C13 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C9 C16 C15 118.6(8) . . ?
C9 C16 C17 121.4(7) . . ?
C15 C16 C17 119.9(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 C19 120.1(7) . . ?
C8 C18 C21 134.4(7) . . ?
C19 C18 C21 105.4(7) . . ?
N1 C19 C5 130.8(7) . . ?
N1 C19 C18 108.1(6) . . ?
C5 C19 C18 120.9(7) . . ?
C25 C20 N1 127.8(7) . . ?
C25 C20 C21 123.9(7) . . ?
N1 C20 C21 108.3(7) . . ?
C20 C21 C22 118.2(7) . . ?
C20 C21 C18 107.9(6) . . ?
C22 C21 C18 133.8(7) . . ?
C23 C22 C21 117.9(7) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 121.2(7) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 122.3(8) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C24 C25 C20 116.4(7) . . ?
C24 C25 H25 121.8 . . ?
C20 C25 H25 121.8 . . ?
C19 N1 C20 110.2(6) . . ?
C19 N1 H1 124.9 . . ?
C20 N1 H1 124.9 . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.062
