# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_a17293
_database_code_depnum_ccdc_archive 'CCDC 1556912'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2568(4)
_cell_length_b                   10.0256(4)
_cell_length_c                   11.0470(5)
_cell_angle_alpha                88.389(3)
_cell_angle_beta                 88.878(2)
_cell_angle_gamma                66.498(2)
_cell_volume                     939.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.64
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_T_max  0.9866
_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            7953
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3200
_reflns_number_gt                2677
_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)+(0.0820P)²+0.0606P] 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         3200
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.07526(18) 0.63853(17) 0.98940(13) 0.0432(4) Uani 1 1 d . . .
C2 C 0.22480(16) 0.51916(16) 0.97468(13) 0.0407(4) Uani 1 1 d . . .
H2 H 0.2543 0.4409 1.0442 0.049 Uiso 1 1 d R . .
C3 C 0.31733(15) 0.49962(15) 0.87593(13) 0.0362(3) Uani 1 1 d . . .
C4 C 0.46245(16) 0.36445(15) 0.86273(13) 0.0372(4) Uani 1 1 d . . .
C5 C 0.47160(18) 0.23230(16) 0.91287(14) 0.0477(4) Uani 1 1 d . . .
H5 H 0.3829 0.2274 0.9543 0.057 Uiso 1 1 calc R . .
C6 C 0.6086(2) 0.10823(18) 0.90283(16) 0.0572(5) Uani 1 1 d . . .
H6 H 0.6136 0.0189 0.9378 0.069 Uiso 1 1 calc R . .
C7 C 0.7383(2) 0.11340(19) 0.84238(16) 0.0575(5) Uani 1 1 d . . .
H7 H 0.8326 0.0282 0.8363 0.069 Uiso 1 1 calc R . .
C8 C 0.73011(18) 0.24315(18) 0.79086(16) 0.0533(4) Uani 1 1 d . . .
H8 H 0.8189 0.2470 0.7487 0.064 Uiso 1 1 calc R . .
C9 C 0.59357(16) 0.36761(17) 0.80013(14) 0.0445(4) Uani 1 1 d . . .
H9 H 0.5889 0.4561 0.7636 0.053 Uiso 1 1 calc R . .
C10 C 0.27838(15) 0.61149(15) 0.77575(12) 0.0349(3) Uani 1 1 d . . .
C11 C 0.27802(15) 0.55484(15) 0.65832(13) 0.0370(4) Uani 1 1 d . . .
C12 C 0.27783(15) 0.49398(15) 0.56589(13) 0.0384(4) Uani 1 1 d . . .
C13 C 0.27308(15) 0.42031(14) 0.45738(12) 0.0355(4) Uani 1 1 d . . .
C14 C 0.39304(17) 0.28710(18) 0.43076(15) 0.0502(4) Uani 1 1 d . . .
H14 H 0.4820 0.2470 0.4821 0.060 Uiso 1 1 calc R . .
C15 C 0.38346(19) 0.21256(19) 0.32976(17) 0.0567(5) Uani 1 1 d . . .
H15 H 0.4663 0.1219 0.3116 0.068 Uiso 1 1 calc R . .
C16 C 0.25391(19) 0.26947(19) 0.25516(15) 0.0522(4) Uani 1 1 d . . .
H16 H 0.2469 0.2173 0.1866 0.063 Uiso 1 1 calc R . .
C17 C 0.13517(18) 0.40173(18) 0.28038(13) 0.0483(4) Uani 1 1 d . . .
H17 H 0.0465 0.4413 0.2287 0.058 Uiso 1 1 calc R . .
C18 C 0.14433(17) 0.47714(16) 0.38027(13) 0.0419(4) Uani 1 1 d . . .
H18 H 0.0621 0.5687 0.3967 0.050 Uiso 1 1 calc R . .
C19 C 0.24705(15) 0.75160(15) 0.80090(13) 0.0384(4) Uani 1 1 d . . .
H19 H 0.2485 0.7706 0.8845 0.046 Uiso 1 1 calc R . .
C20 C 0.21128(15) 0.87870(15) 0.72004(14) 0.0384(4) Uani 1 1 d . . .
C21 C 0.20203(17) 0.87659(17) 0.59414(14) 0.0474(4) Uani 1 1 d . . .
H21 H 0.2121 0.7894 0.5562 0.057 Uiso 1 1 calc R . .
C22 C 0.17839(19) 0.99971(17) 0.52389(16) 0.0543(5) Uani 1 1 d . . .
H22 H 0.1740 0.9959 0.4383 0.065 Uiso 1 1 calc R . .
C23 C 0.16126(18) 1.12763(17) 0.57686(17) 0.0560(5) Uani 1 1 d . . .
H23 H 0.1452 1.2118 0.5281 0.067 Uiso 1 1 calc R . .
C24 C 0.16740(19) 1.13327(17) 0.70087(18) 0.0564(5) Uani 1 1 d . . .
H24 H 0.1549 1.2218 0.7377 0.068 Uiso 1 1 calc R . .
C25 C 0.19175(17) 1.01035(16) 0.77236(15) 0.0473(4) Uani 1 1 d . . .
H25 H 0.1952 1.0156 0.8579 0.057 Uiso 1 1 calc R . .
N1 N -0.04697(16) 0.72961(16) 1.00448(13) 0.0564(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.1485(19) . ?
C1 C2 1.434(2) . ?
C2 C3 1.343(2) . ?
C2 H2 1.0414 . ?
C3 C4 1.4879(18) . ?
C3 C10 1.4953(19) . ?
C4 C5 1.393(2) . ?
C4 C9 1.396(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C19 1.352(2) . ?
C10 C11 1.431(2) . ?
C11 C12 1.2045(19) . ?
C12 C13 1.436(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.393(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.464(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(2) . ?
C20 C25 1.399(2) . ?
C21 C22 1.382(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.374(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 176.62(17) . . ?
C3 C2 C1 124.33(13) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 114.8 . . ?
C2 C3 C4 120.65(13) . . ?
C2 C3 C10 121.55(12) . . ?
C4 C3 C10 117.80(12) . . ?
C5 C4 C9 118.37(13) . . ?
C5 C4 C3 121.13(13) . . ?
C9 C4 C3 120.49(13) . . ?
C6 C5 C4 120.58(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.44(15) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 119.57(15) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.41(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 120.60(14) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C19 C10 C11 126.15(13) . . ?
C19 C10 C3 119.98(13) . . ?
C11 C10 C3 113.87(12) . . ?
C12 C11 C10 172.97(15) . . ?
C11 C12 C13 177.98(14) . . ?
C14 C13 C18 118.76(13) . . ?
C14 C13 C12 120.48(13) . . ?
C18 C13 C12 120.68(12) . . ?
C15 C14 C13 120.25(14) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.26(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.86(15) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.24(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.62(13) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C10 C19 C20 130.41(14) . . ?
C10 C19 H19 114.8 . . ?
C20 C19 H19 114.8 . . ?
C21 C20 C25 117.69(14) . . ?
C21 C20 C19 124.73(14) . . ?
C25 C20 C19 117.52(14) . . ?
C22 C21 C20 120.89(15) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.56(17) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.71(15) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.30(16) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.82(16) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_a17319
_database_code_depnum_ccdc_archive 'CCDC 1556913'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   13.773(3)
_cell_length_b                   7.1192(14)
_cell_length_c                   19.135(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.972(4)
_cell_angle_gamma                90.00
_cell_volume                     1862.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  0.9980
_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            11134
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.13
_reflns_number_total             3313
_reflns_number_gt                2027
_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)+(0.0488P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3313
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 -0.00924(12) 0.2280(3) 0.25221(11) 0.0530(5) Uani 1 1 d . . .
C2 C -0.02022(12) 0.2212(2) 0.32529(9) 0.0458(5) Uani 1 1 d . . .
H2 H -0.0842 0.2075 0.3383 0.055 Uiso 1 1 calc R . .
C3 C 0.05509(11) 0.2331(2) 0.37659(9) 0.0376(4) Uani 1 1 d . . .
C4 C 0.15718(11) 0.2402(2) 0.35903(8) 0.0389(4) Uani 1 1 d . . .
C5 C 0.19374(12) 0.0948(3) 0.32205(9) 0.0501(5) Uani 1 1 d . . .
H5 H 0.1529 -0.0089 0.3073 0.060 Uiso 1 1 calc R . .
C6 C 0.28890(13) 0.0985(3) 0.30628(10) 0.0660(7) Uani 1 1 d . . .
H6 H 0.3135 -0.0026 0.2813 0.079 Uiso 1 1 calc R . .
C7 C 0.34794(13) 0.2495(4) 0.32699(10) 0.0708(7) Uani 1 1 d . . .
H7 H 0.4137 0.2515 0.3168 0.085 Uiso 1 1 calc R . .
C8 C 0.31209(12) 0.3978(3) 0.36239(9) 0.0616(6) Uani 1 1 d . . .
H8 H 0.3525 0.5034 0.3754 0.074 Uiso 1 1 calc R . .
C9 C 0.21763(11) 0.3926(3) 0.37894(9) 0.0482(5) Uani 1 1 d . . .
H9 H 0.1935 0.4938 0.4042 0.058 Uiso 1 1 calc R . .
C10 C 0.03668(11) 0.2388(2) 0.45134(9) 0.0367(4) Uani 1 1 d . . .
C11 C 0.11136(11) 0.2218(2) 0.50412(8) 0.0398(4) Uani 1 1 d . . .
H11 H 0.1738 0.2036 0.4889 0.048 Uiso 1 1 calc R . .
C12 C 0.11177(12) 0.2267(2) 0.58030(9) 0.0408(4) Uani 1 1 d . . .
C13 C 0.19796(13) 0.1754(3) 0.62164(10) 0.0541(5) Uani 1 1 d . . .
H13 H 0.2527 0.1367 0.5995 0.065 Uiso 1 1 calc R . .
C14 C 0.20524(15) 0.1799(3) 0.69465(11) 0.0681(6) Uani 1 1 d . . .
H14 H 0.2643 0.1428 0.7221 0.082 Uiso 1 1 calc R . .
C15 C 0.12634(17) 0.2385(3) 0.72727(11) 0.0689(6) Uani 1 1 d . . .
H15 H 0.1309 0.2423 0.7772 0.083 Uiso 1 1 calc R . .
C16 C 0.04113(16) 0.2912(3) 0.68696(10) 0.0612(6) Uani 1 1 d . . .
H16 H -0.0129 0.3329 0.7093 0.073 Uiso 1 1 calc R . .
C17 C 0.03338(13) 0.2841(2) 0.61472(10) 0.0511(5) Uani 1 1 d . . .
H17 H -0.0265 0.3190 0.5878 0.061 Uiso 1 1 calc R . .
C18 C -0.06367(12) 0.2562(2) 0.46258(8) 0.0393(4) Uani 1 1 d . . .
C19 C -0.15005(12) 0.2659(2) 0.46618(9) 0.0418(4) Uani 1 1 d . . .
C20 C -0.25275(11) 0.2714(2) 0.47161(9) 0.0387(4) Uani 1 1 d . . .
C21 C -0.29216(12) 0.1667(3) 0.52239(9) 0.0495(5) Uani 1 1 d . . .
H21 H -0.2504 0.0927 0.5546 0.059 Uiso 1 1 calc R . .
C22 C -0.39144(13) 0.1690(3) 0.52669(11) 0.0595(6) Uani 1 1 d . . .
H22 H -0.4178 0.0958 0.5614 0.071 Uiso 1 1 calc R . .
C23 C -0.45210(13) 0.2774(3) 0.48069(11) 0.0647(6) Uani 1 1 d . . .
H23 H -0.5205 0.2791 0.4835 0.078 Uiso 1 1 calc R . .
C24 C -0.41390(13) 0.3832(3) 0.43075(11) 0.0643(6) Uani 1 1 d . . .
H24 H -0.4560 0.4586 0.3993 0.077 Uiso 1 1 calc R . .
C25 C -0.31525(12) 0.3809(3) 0.42583(9) 0.0519(5) Uani 1 1 d . . .
H25 H -0.2896 0.4546 0.3910 0.062 Uiso 1 1 calc R . .
N1 N -0.00438(12) 0.2366(3) 0.19305(10) 0.0770(6) 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 N1 1.144(2) . ?
C1 C2 1.425(2) . ?
C2 C3 1.341(2) . ?
C2 H2 0.9500 . ?
C3 C10 1.483(2) . ?
C3 C4 1.486(2) . ?
C4 C5 1.383(2) . ?
C4 C9 1.392(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.357(2) . ?
C10 C18 1.430(2) . ?
C11 C12 1.458(2) . ?
C11 H11 0.9500 . ?
C12 C17 1.392(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.202(2) . ?
C19 C20 1.431(2) . ?
C20 C21 1.386(2) . ?
C20 C25 1.390(2) . ?
C21 C22 1.380(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.371(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 177.06(19) . . ?
C3 C2 C1 123.44(14) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C2 C3 C10 120.00(13) . . ?
C2 C3 C4 120.37(14) . . ?
C10 C3 C4 119.63(14) . . ?
C5 C4 C9 118.71(15) . . ?
C5 C4 C3 120.25(15) . . ?
C9 C4 C3 121.04(15) . . ?
C6 C5 C4 120.79(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.69(19) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.35(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.84(19) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.58(18) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C11 C10 C18 123.72(14) . . ?
C11 C10 C3 120.84(13) . . ?
C18 C10 C3 115.40(14) . . ?
C10 C11 C12 130.77(14) . . ?
C10 C11 H11 114.6 . . ?
C12 C11 H11 114.6 . . ?
C17 C12 C13 117.69(17) . . ?
C17 C12 C11 124.83(16) . . ?
C13 C12 C11 117.46(15) . . ?
C14 C13 C12 121.18(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.54(19) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.71(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 121.09(19) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C10 174.41(17) . . ?
C18 C19 C20 178.04(19) . . ?
C21 C20 C25 118.53(15) . . ?
C21 C20 C19 120.72(16) . . ?
C25 C20 C19 120.74(15) . . ?
C22 C21 C20 120.71(18) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.86(18) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 119.99(17) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.53(18) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 120.36(17) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_ch15278
_database_code_depnum_ccdc_archive 'CCDC 1557911'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 O'
_chemical_formula_sum            'C25 H18 O'
_chemical_formula_weight         334.39

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'
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/n'

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

_cell_length_a                   10.3643(11)
_cell_length_b                   12.1725(13)
_cell_length_c                   14.7261(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.592(4)
_cell_angle_gamma                90.00
_cell_volume                     1841.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.78
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9460
_exptl_absorpt_correction_T_max  0.9829
_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  ?
_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            9099
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.07
_reflns_number_total             3202
_reflns_number_gt                2339
_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)+(0.0875P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.17447(18) 1.09900(15) 0.52491(13) 0.0371(5) Uani 1 1 d . . .
H1 H 0.1447 1.1676 0.4995 0.045 Uiso 1 1 calc R . .
C2 C 0.15594(18) 1.00255(14) 0.46693(12) 0.0330(5) Uani 1 1 d . . .
H2 H 0.1832 0.9337 0.4932 0.040 Uiso 1 1 calc R . .
C3 C 0.10286(16) 1.00376(13) 0.37856(12) 0.0278(4) Uani 1 1 d . . .
C4 C 0.08055(16) 0.90105(14) 0.32505(12) 0.0284(4) Uani 1 1 d . . .
C5 C 0.10401(17) 0.79952(14) 0.37440(12) 0.0317(4) Uani 1 1 d . . .
C6 C 0.13050(17) 0.71709(14) 0.41702(12) 0.0323(5) Uani 1 1 d . . .
C7 C 0.15732(17) 0.61604(14) 0.46542(12) 0.0314(4) Uani 1 1 d . . .
C8 C 0.20760(18) 0.61591(16) 0.55733(13) 0.0412(5) Uani 1 1 d . . .
H8 H 0.2274 0.6836 0.5881 0.049 Uiso 1 1 calc R . .
C9 C 0.2292(2) 0.51843(18) 0.60475(14) 0.0477(6) Uani 1 1 d . . .
H9 H 0.2643 0.5192 0.6677 0.057 Uiso 1 1 calc R . .
C10 C 0.1997(2) 0.41967(17) 0.56047(15) 0.0469(6) Uani 1 1 d . . .
H10 H 0.2139 0.3524 0.5930 0.056 Uiso 1 1 calc R . .
C11 C 0.1499(2) 0.41898(16) 0.46941(14) 0.0487(6) Uani 1 1 d . . .
H11 H 0.1297 0.3510 0.4392 0.058 Uiso 1 1 calc R . .
C12 C 0.1290(2) 0.51564(15) 0.42144(13) 0.0408(5) Uani 1 1 d . . .
H12 H 0.0953 0.5141 0.3583 0.049 Uiso 1 1 calc R . .
C13 C 0.04597(17) 0.90435(14) 0.23336(12) 0.0311(4) Uani 1 1 d . . .
H13 H 0.0375 0.9760 0.2077 0.037 Uiso 1 1 calc R . .
C14 C 0.01960(17) 0.81462(14) 0.16780(12) 0.0332(5) Uani 1 1 d . . .
C15 C -0.02743(18) 0.71166(15) 0.18938(14) 0.0408(5) Uani 1 1 d . . .
H15 H -0.0415 0.6955 0.2504 0.049 Uiso 1 1 calc R . .
C16 C -0.0536(2) 0.63266(17) 0.12071(17) 0.0554(6) Uani 1 1 d . . .
H16 H -0.0866 0.5629 0.1351 0.066 Uiso 1 1 calc R . .
C17 C -0.0321(2) 0.6551(2) 0.03225(17) 0.0601(7) Uani 1 1 d . . .
H17 H -0.0493 0.6005 -0.0138 0.072 Uiso 1 1 calc R . .
C18 C 0.0142(2) 0.7559(2) 0.01046(16) 0.0603(7) Uani 1 1 d . . .
H18 H 0.0301 0.7709 -0.0504 0.072 Uiso 1 1 calc R . .
C19 C 0.03757(19) 0.83529(18) 0.07715(13) 0.0447(5) Uani 1 1 d . . .
H19 H 0.0666 0.9058 0.0611 0.054 Uiso 1 1 calc R . .
C20 C 0.06372(16) 1.10870(13) 0.32960(11) 0.0269(4) Uani 1 1 d . . .
C21 C -0.06733(17) 1.13569(15) 0.30872(12) 0.0330(4) Uani 1 1 d . . .
H21 H -0.1321 1.0881 0.3266 0.040 Uiso 1 1 calc R . .
C22 C -0.10354(19) 1.23193(15) 0.26182(12) 0.0366(5) Uani 1 1 d . . .
H22 H -0.1930 1.2506 0.2482 0.044 Uiso 1 1 calc R . .
C23 C -0.0097(2) 1.30039(15) 0.23503(12) 0.0387(5) Uani 1 1 d . . .
H23 H -0.0347 1.3663 0.2029 0.046 Uiso 1 1 calc R . .
C24 C 0.1193(2) 1.27389(16) 0.25447(14) 0.0436(5) Uani 1 1 d . . .
H24 H 0.1834 1.3212 0.2354 0.052 Uiso 1 1 calc R . .
C25 C 0.15668(18) 1.17799(15) 0.30210(13) 0.0371(5) Uani 1 1 d . . .
H25 H 0.2464 1.1601 0.3157 0.045 Uiso 1 1 calc R . .
O1 O 0.22577(14) 1.09740(11) 0.60394(9) 0.0482(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.214(2) . ?
C1 C2 1.450(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.344(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.480(2) . ?
C3 C20 1.496(2) . ?
C4 C13 1.351(2) . ?
C4 C5 1.438(2) . ?
C5 C6 1.196(2) . ?
C6 C7 1.430(2) . ?
C7 C8 1.385(2) . ?
C7 C12 1.396(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.459(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(3) . ?
C14 C19 1.395(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.381(2) . ?
C20 C21 1.392(2) . ?
C21 C22 1.386(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 123.97(17) . . ?
O1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 124.52(16) . . ?
C3 C2 H2 117.7 . . ?
C1 C2 H2 117.7 . . ?
C2 C3 C4 121.43(15) . . ?
C2 C3 C20 121.74(15) . . ?
C4 C3 C20 116.83(15) . . ?
C13 C4 C5 122.38(16) . . ?
C13 C4 C3 120.61(15) . . ?
C5 C4 C3 116.93(15) . . ?
C6 C5 C4 176.32(19) . . ?
C5 C6 C7 177.35(18) . . ?
C8 C7 C12 118.77(17) . . ?
C8 C7 C6 120.75(16) . . ?
C12 C7 C6 120.44(16) . . ?
C9 C8 C7 120.71(18) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.87(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.84(18) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.70(19) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.11(18) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C4 C13 C14 129.83(16) . . ?
C4 C13 H13 115.1 . . ?
C14 C13 H13 115.1 . . ?
C15 C14 C19 118.32(17) . . ?
C15 C14 C13 124.17(18) . . ?
C19 C14 C13 117.45(17) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C25 C20 C21 119.30(16) . . ?
C25 C20 C3 120.50(15) . . ?
C21 C20 C3 120.16(15) . . ?
C22 C21 C20 120.10(17) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.94(18) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.31(17) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.22(18) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.12(17) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_a17448
_database_code_depnum_ccdc_archive 'CCDC 1556914'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 O2'
_chemical_formula_sum            'C26 H20 O2'
_chemical_formula_weight         364.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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                   12.480(3)
_cell_length_b                   5.9054(12)
_cell_length_c                   27.814(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.720(18)
_cell_angle_gamma                90.00
_cell_volume                     2042.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9963
_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            12390
_diffrn_reflns_av_R_equivalents  0.1502
_diffrn_reflns_av_sigmaI/netI    0.2225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3525
_reflns_number_gt                1514
_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)+(0.0660P)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       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3525
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2411
_refine_ls_R_factor_gt           0.1106
_refine_ls_wR_factor_ref         0.2084
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.7070(4) 0.4984(8) 0.01335(18) 0.0385(14) Uani 1 1 d . . .
C2 C 0.6200(4) 0.7144(9) -0.05035(18) 0.0604(17) Uani 1 1 d . . .
H2A H 0.5478 0.6551 -0.0448 0.073 Uiso 1 1 d R . .
H2B H 0.6312 0.7432 -0.0847 0.073 Uiso 1 1 d R . .
H2C H 0.6255 0.8585 -0.0327 0.073 Uiso 1 1 d R . .
C3 C 0.7970(4) 0.3425(8) 0.02471(15) 0.0375(13) Uani 1 1 d . . .
H3 H 0.8492 0.3302 0.0019 0.045 Uiso 1 1 calc R . .
C4 C 0.8116(4) 0.2154(7) 0.06486(15) 0.0307(13) Uani 1 1 d . . .
C5 C 0.7333(4) 0.2076(7) 0.10228(15) 0.0281(12) Uani 1 1 d . . .
C6 C 0.6450(4) 0.0762(7) 0.09719(15) 0.0329(13) Uani 1 1 d . . .
H6 H 0.6358 -0.0054 0.0677 0.039 Uiso 1 1 calc R . .
C7 C 0.5610(4) 0.0400(8) 0.13017(16) 0.0339(13) Uani 1 1 d . . .
C8 C 0.4985(4) -0.1558(8) 0.12502(19) 0.0501(15) Uani 1 1 d . . .
H8 H 0.5123 -0.2631 0.1009 0.060 Uiso 1 1 calc R . .
C9 C 0.4176(5) -0.1953(9) 0.1543(2) 0.0678(18) Uani 1 1 d . . .
H9 H 0.3756 -0.3293 0.1504 0.081 Uiso 1 1 calc R . .
C10 C 0.3970(4) -0.0416(10) 0.1895(2) 0.0676(18) Uani 1 1 d . . .
H10 H 0.3409 -0.0692 0.2099 0.081 Uiso 1 1 calc R . .
C11 C 0.4573(4) 0.1510(9) 0.19507(19) 0.0572(16) Uani 1 1 d . . .
H11 H 0.4431 0.2571 0.2194 0.069 Uiso 1 1 calc R . .
C12 C 0.5386(4) 0.1927(8) 0.16567(17) 0.0413(13) Uani 1 1 d . . .
H12 H 0.5798 0.3278 0.1698 0.050 Uiso 1 1 calc R . .
C13 C 0.7662(4) 0.3370(8) 0.14484(17) 0.0360(13) Uani 1 1 d . . .
C14 C 0.7962(4) 0.4482(8) 0.17883(17) 0.0377(13) Uani 1 1 d . . .
C15 C 0.8199(4) 0.5924(8) 0.22045(15) 0.0336(13) Uani 1 1 d . . .
C17 C 0.7852(4) 0.9351(9) 0.2622(2) 0.0619(17) Uani 1 1 d . . .
H17 H 0.7494 1.0767 0.2635 0.074 Uiso 1 1 calc R . .
C18 C 0.8543(5) 0.8659(10) 0.3002(2) 0.0616(17) Uani 1 1 d . . .
H18 H 0.8649 0.9595 0.3280 0.074 Uiso 1 1 calc R . .
C19 C 0.9084(4) 0.6639(10) 0.29888(18) 0.0582(16) Uani 1 1 d . . .
H19 H 0.9568 0.6193 0.3253 0.070 Uiso 1 1 calc R . .
C20 C 0.8919(4) 0.5253(8) 0.25867(16) 0.0418(14) Uani 1 1 d . . .
H20 H 0.9294 0.3857 0.2572 0.050 Uiso 1 1 calc R . .
C21 C 0.9102(4) 0.0741(8) 0.07399(15) 0.0315(12) Uani 1 1 d . . .
C22 C 0.9048(4) -0.1350(8) 0.09693(15) 0.0403(14) Uani 1 1 d . . .
H22 H 0.8384 -0.1852 0.1076 0.048 Uiso 1 1 calc R . .
C23 C 0.9952(5) -0.2700(8) 0.10436(17) 0.0476(15) Uani 1 1 d . . .
H23 H 0.9895 -0.4135 0.1193 0.057 Uiso 1 1 calc R . .
C24 C 1.0919(4) -0.2014(9) 0.09068(17) 0.0476(15) Uani 1 1 d . . .
H24 H 1.1536 -0.2950 0.0964 0.057 Uiso 1 1 calc R . .
C25 C 1.0997(4) 0.0071(9) 0.06827(17) 0.0487(15) Uani 1 1 d . . .
H25 H 1.1670 0.0575 0.0587 0.058 Uiso 1 1 calc R . .
C26 C 1.0092(4) 0.1419(8) 0.05977(15) 0.0373(13) Uani 1 1 d . . .
H26 H 1.0152 0.2833 0.0439 0.045 Uiso 1 1 calc R . .
C27 C 0.7679(4) 0.7992(8) 0.22239(17) 0.0441(14) Uani 1 1 d . . .
H27 H 0.7201 0.8470 0.1960 0.053 Uiso 1 1 calc R . .
O1 O 0.6411(3) 0.5626(5) 0.03896(12) 0.0531(11) Uani 1 1 d . . .
O2 O 0.7062(3) 0.5621(6) -0.03306(11) 0.0545(11) 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 1.193(5) . ?
C1 O2 1.344(5) . ?
C1 C3 1.467(6) . ?
C2 O2 1.453(5) . ?
C2 H2A 0.9908 . ?
C2 H2B 0.9909 . ?
C2 H2C 0.9823 . ?
C3 C4 1.345(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.485(6) . ?
C4 C21 1.492(6) . ?
C5 C6 1.346(5) . ?
C5 C13 1.440(6) . ?
C6 C7 1.464(6) . ?
C6 H6 0.9500 . ?
C7 C12 1.383(6) . ?
C7 C8 1.396(6) . ?
C8 C9 1.370(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.366(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.186(5) . ?
C14 C15 1.448(6) . ?
C15 C27 1.386(6) . ?
C15 C20 1.391(5) . ?
C17 C18 1.369(7) . ?
C17 C27 1.371(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.387(6) . ?
C21 C22 1.394(6) . ?
C22 C23 1.383(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.357(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 122.3(5) . . ?
O1 C1 C3 128.6(5) . . ?
O2 C1 C3 109.1(5) . . ?
O2 C2 H2A 112.8 . . ?
O2 C2 H2B 105.4 . . ?
H2A C2 H2B 114.4 . . ?
O2 C2 H2C 110.6 . . ?
H2A C2 H2C 104.8 . . ?
H2B C2 H2C 108.9 . . ?
C4 C3 C1 125.3(5) . . ?
C4 C3 H3 117.3 . . ?
C1 C3 H3 117.3 . . ?
C3 C4 C5 123.2(4) . . ?
C3 C4 C21 120.5(5) . . ?
C5 C4 C21 116.4(4) . . ?
C6 C5 C13 124.6(5) . . ?
C6 C5 C4 121.6(4) . . ?
C13 C5 C4 113.6(4) . . ?
C5 C6 C7 129.8(4) . . ?
C5 C6 H6 115.1 . . ?
C7 C6 H6 115.1 . . ?
C12 C7 C8 118.0(5) . . ?
C12 C7 C6 123.3(5) . . ?
C8 C7 C6 118.7(5) . . ?
C9 C8 C7 120.9(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.1(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.6(5) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C14 C13 C5 177.3(5) . . ?
C13 C14 C15 173.3(5) . . ?
C27 C15 C20 119.7(4) . . ?
C27 C15 C14 118.9(4) . . ?
C20 C15 C14 121.3(4) . . ?
C18 C17 C27 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C27 C17 H17 120.1 . . ?
C17 C18 C19 121.2(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
C26 C21 C22 117.6(4) . . ?
C26 C21 C4 122.1(4) . . ?
C22 C21 C4 120.2(5) . . ?
C23 C22 C21 120.6(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 121.3(5) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.2(5) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 121.2(5) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C17 C27 C15 120.3(4) . . ?
C17 C27 H27 119.9 . . ?
C15 C27 H27 119.9 . . ?
C1 O2 C2 115.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_15371a
_database_code_depnum_ccdc_archive 'CCDC 1557912'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   22.492(3)
_cell_length_b                   3.9450(5)
_cell_length_c                   20.893(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.820(9)
_cell_angle_gamma                90.00
_cell_volume                     1708.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9978
_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  ?
_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            12026
_diffrn_reflns_av_R_equivalents  0.1490
_diffrn_reflns_av_sigmaI/netI    0.1460
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         0.98
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3009
_reflns_number_gt                1551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.1550P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3009
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1852
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2966
_refine_ls_wR_factor_gt          0.2358
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.3051(2) 0.2298(12) 0.3295(2) 0.0234(12) Uani 1 1 d . . .
C2 C 0.2442(2) 0.2942(12) 0.2677(2) 0.0219(12) Uani 1 1 d . B .
C3 C 0.2482(3) 0.4571(13) 0.2104(3) 0.0289(13) Uani 1 1 d . . .
H3 H 0.2891 0.5262 0.2114 0.035 Uiso 1 1 calc R B .
C4 C 0.1932(3) 0.5183(14) 0.1522(3) 0.0323(13) Uani 1 1 d . B .
H4 H 0.1964 0.6292 0.1133 0.039 Uiso 1 1 calc R . .
C5 C 0.1344(3) 0.4205(14) 0.1502(3) 0.0360(14) Uani 1 1 d . . .
H5 H 0.0967 0.4687 0.1103 0.043 Uiso 1 1 calc R B .
C6 C 0.1291(3) 0.2511(13) 0.2060(3) 0.0315(13) Uani 1 1 d . B .
H6 H 0.0882 0.1796 0.2043 0.038 Uiso 1 1 calc R . .
C7 C 0.1845(3) 0.1879(12) 0.2642(3) 0.0273(13) Uani 1 1 d . . .
H7 H 0.1814 0.0695 0.3024 0.033 Uiso 1 1 calc R B .
C8 C 0.3099(2) 0.2882(12) 0.3979(2) 0.0225(12) Uani 1 1 d . B .
C9 C 0.2568(2) 0.4343(12) 0.4103(2) 0.0231(12) Uani 1 1 d . . .
C10 C 0.2103(2) 0.5540(13) 0.4163(2) 0.0251(12) Uani 1 1 d . B .
C11 C 0.1516(3) 0.6823(12) 0.4180(3) 0.0256(12) Uani 1 1 d . . .
C12 C 0.0944(3) 0.6580(14) 0.3597(3) 0.0318(13) Uani 1 1 d . B .
H12 H 0.0951 0.5605 0.3184 0.038 Uiso 1 1 calc R . .
C13 C 0.0364(3) 0.7727(14) 0.3604(3) 0.0415(15) Uani 1 1 d . . .
H13 H -0.0022 0.7527 0.3201 0.050 Uiso 1 1 calc R B .
C14 C 0.0353(3) 0.9171(14) 0.4206(3) 0.0383(15) Uani 1 1 d . B .
H14 H -0.0042 0.9951 0.4218 0.046 Uiso 1 1 calc R . .
C15 C 0.0919(3) 0.9465(14) 0.4786(3) 0.0342(14) Uani 1 1 d . . .
H15 H 0.0911 1.0505 0.5193 0.041 Uiso 1 1 calc R B .
C16 C 0.1493(3) 0.8274(13) 0.4783(3) 0.0298(13) Uani 1 1 d . B .
H16 H 0.1875 0.8434 0.5192 0.036 Uiso 1 1 calc R . .
C17 C 0.3689(2) 0.2174(12) 0.4536(2) 0.0239(12) Uani 1 1 d . . .
C18 C 0.3784(2) 0.2572(12) 0.5279(2) 0.0230(12) Uani 1 1 d . B .
C19 C 0.3341(3) 0.1239(12) 0.5528(3) 0.0273(12) Uani 1 1 d . . .
H19 H 0.2958 0.0185 0.5218 0.033 Uiso 1 1 calc R B .
C20 C 0.3459(3) 0.1452(14) 0.6233(3) 0.0341(14) Uani 1 1 d . B .
H20 H 0.3160 0.0515 0.6404 0.041 Uiso 1 1 calc R . .
C21 C 0.4003(3) 0.3003(14) 0.6677(3) 0.0364(14) Uani 1 1 d . . .
H21 H 0.4080 0.3145 0.7157 0.044 Uiso 1 1 calc R B .
C22 C 0.4442(3) 0.4364(14) 0.6440(3) 0.0362(14) Uani 1 1 d . B .
H22 H 0.4816 0.5480 0.6754 0.043 Uiso 1 1 calc R . .
C23 C 0.4337(3) 0.4103(13) 0.5738(3) 0.0294(13) Uani 1 1 d . . .
H23 H 0.4647 0.4979 0.5575 0.035 Uiso 1 1 calc R B .
C25 C 0.4123(3) 0.0632(14) 0.3721(3) 0.0361(14) Uani 1 1 d . . .
H25 H 0.4484 -0.0117 0.3631 0.043 Uiso 1 1 calc R A 1
N1 N 0.3567 0.1178 0.3163 0.025 Uiso 0.50 1 d P B 1
C24 C 0.4213 0.1064 0.4410 0.023 Uiso 0.50 1 d P B 1
H24 H 0.4617 0.0617 0.4777 0.028 Uiso 0.50 1 calc PR B 1
C24' C 0.3566 0.1179 0.3165 0.025 Uiso 0.50 1 d P B 2
H24' H 0.3537 0.0798 0.2705 0.030 Uiso 0.50 1 calc PR B 2
N1' N 0.4213 0.1064 0.4410 0.023 Uiso 0.50 1 d P B 2


_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 C24' 1.362(5) . ?
C1 N1 1.365(5) . ?
C1 C8 1.409(6) . ?
C1 C2 1.496(7) . ?
C2 C7 1.381(7) . ?
C2 C3 1.393(6) . ?
C3 C4 1.379(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C17 1.413(7) . ?
C8 C9 1.437(7) . ?
C9 C10 1.197(6) . ?
C10 C11 1.427(7) . ?
C11 C12 1.390(7) . ?
C11 C16 1.405(6) . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1' 1.375(5) . ?
C17 C24 1.375(5) . ?
C17 C18 1.492(6) . ?
C18 C23 1.381(7) . ?
C18 C19 1.394(6) . ?
C19 C20 1.393(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.361(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C24' 1.355(5) . ?
C25 N1 1.356(5) . ?
C25 C24 1.383(5) . ?
C25 N1' 1.383(5) . ?
C25 H25 0.9500 . ?
C24 H24 0.9500 . ?
C24' H24' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24' C1 N1 0.101(1) . . ?
C24' C1 C8 121.3(4) . . ?
N1 C1 C8 121.4(4) . . ?
C24' C1 C2 116.7(4) . . ?
N1 C1 C2 116.6(4) . . ?
C8 C1 C2 122.0(4) . . ?
C7 C2 C3 118.8(5) . . ?
C7 C2 C1 122.8(4) . . ?
C3 C2 C1 118.4(5) . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C2 C7 C6 121.1(5) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C1 C8 C17 118.7(4) . . ?
C1 C8 C9 120.5(4) . . ?
C17 C8 C9 120.7(4) . . ?
C10 C9 C8 175.9(5) . . ?
C9 C10 C11 175.0(5) . . ?
C12 C11 C16 118.1(5) . . ?
C12 C11 C10 120.3(4) . . ?
C16 C11 C10 121.6(5) . . ?
C13 C12 C11 121.5(5) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.4(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.3(5) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N1' C17 C24 0.0 . . ?
N1' C17 C8 120.5(4) . . ?
C24 C17 C8 120.5(4) . . ?
N1' C17 C18 116.5(4) . . ?
C24 C17 C18 116.5(4) . . ?
C8 C17 C18 123.1(4) . . ?
C23 C18 C19 119.3(5) . . ?
C23 C18 C17 119.6(4) . . ?
C19 C18 C17 121.0(4) . . ?
C20 C19 C18 120.0(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.8(5) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.0(5) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24' C25 N1 0.163(1) . . ?
C24' C25 C24 125.9(4) . . ?
N1 C25 C24 126.1(4) . . ?
C24' C25 N1' 125.9(4) . . ?
N1 C25 N1' 126.1(4) . . ?
C24 C25 N1' 0.0 . . ?
C24' C25 H25 117.1 . . ?
N1 C25 H25 117.0 . . ?
C24 C25 H25 117.0 . . ?
N1' C25 H25 117.0 . . ?
C25 N1 C1 116.8(3) . . ?
C17 C24 C25 116.6(3) . . ?
C17 C24 H24 121.7 . . ?
C25 C24 H24 121.7 . . ?
C25 C24' C1 117.1(3) . . ?
C25 C24' H24' 121.5 . . ?
C1 C24' H24' 121.5 . . ?
C17 N1' C25 116.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.099
