# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1452906'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1-(1-phenyl-3-p-tolyl-1H-indeno[2,1-c]pyridin-2(9H)-yl)ethanone
_chemical_name_common            'Fused Indeno Pyridine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 N O'
_chemical_formula_sum            'C27 H23 N O'
_chemical_formula_weight         377.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.799(8)
_cell_length_b                   10.489(6)
_cell_length_c                   17.066(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.461(12)
_cell_angle_gamma                90
_cell_volume                     2036(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14425
_diffrn_reflns_av_unetI/netI     0.1386
_diffrn_reflns_av_R_equivalents  0.1348
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3762
_reflns_number_gt                1795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1312
_refine_ls_goodness_of_fit_ref   0.731
_refine_ls_restrained_S_all      0.731
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.58010(18) 0.9614(2) 0.09744(13) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.73989(19) 0.8338(2) 0.13251(13) 0.0278(6) Uani 1 1 d . . . . .
C2 C 0.6266(3) 0.8599(3) 0.08888(17) 0.0350(7) Uani 1 1 d . . . . .
C3 C 0.5621(3) 0.7634(3) 0.02782(18) 0.0464(9) Uani 1 1 d . . . . .
H3A H 0.5023 0.8056 -0.0133 0.070 Uiso 1 1 calc R U . . .
H3B H 0.5263 0.7010 0.0547 0.070 Uiso 1 1 calc R U . . .
H3C H 0.6165 0.7222 0.0031 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7960(2) 0.7126(3) 0.13729(16) 0.0273(7) Uani 1 1 d . . . . .
C5 C 0.9092(2) 0.7098(3) 0.13698(15) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.9489 0.6324 0.1416 0.033 Uiso 1 1 calc R U . . .
C6 C 0.9701(2) 0.8274(3) 0.12948(16) 0.0283(7) Uani 1 1 d . . . . .
C7 C 0.9244(2) 0.9394(3) 0.14488(16) 0.0276(7) Uani 1 1 d . . . . .
C8 C 0.8144(2) 0.9414(3) 0.17269(16) 0.0281(7) Uani 1 1 d . . . . .
H8 H 0.7726 1.0210 0.1538 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0777(2) 0.8495(3) 0.10487(16) 0.0292(7) Uani 1 1 d . . . . .
C10 C 1.1557(2) 0.7668(3) 0.08437(17) 0.0362(7) Uani 1 1 d . . . . .
H10 H 1.1439 0.6792 0.0854 0.043 Uiso 1 1 calc R U . . .
C11 C 1.2513(3) 0.8152(3) 0.06237(18) 0.0424(8) Uani 1 1 d . . . . .
H11 H 1.3042 0.7597 0.0485 0.051 Uiso 1 1 calc R U . . .
C12 C 1.2698(3) 0.9467(4) 0.06065(19) 0.0456(9) Uani 1 1 d . . . . .
H12 H 1.3348 0.9785 0.0459 0.055 Uiso 1 1 calc R U . . .
C13 C 1.1906(3) 1.0291(3) 0.08108(18) 0.0416(8) Uani 1 1 d . . . . .
H13 H 1.2020 1.1167 0.0794 0.050 Uiso 1 1 calc R U . . .
C14 C 1.0952(2) 0.9821(3) 0.10381(16) 0.0315(7) Uani 1 1 d . . . . .
C15 C 0.9982(2) 1.0474(3) 0.13045(18) 0.0345(7) Uani 1 1 d . . . . .
H15A H 1.0293 1.0961 0.1798 0.041 Uiso 1 1 calc R U . . .
H15B H 0.9536 1.1037 0.0884 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8319(2) 0.9320(3) 0.26438(16) 0.0292(7) Uani 1 1 d . . . . .
C17 C 0.9382(3) 0.8969(3) 0.31705(17) 0.0352(7) Uani 1 1 d . . . . .
H17 H 1.0036 0.8847 0.2973 0.042 Uiso 1 1 calc R U . . .
C18 C 0.9476(3) 0.8798(3) 0.39944(18) 0.0476(9) Uani 1 1 d . . . . .
H18 H 1.0192 0.8571 0.4349 0.057 Uiso 1 1 calc R U . . .
C19 C 0.8494(3) 0.8969(3) 0.4283(2) 0.0491(9) Uani 1 1 d . . . . .
H19 H 0.8550 0.8842 0.4832 0.059 Uiso 1 1 calc R U . . .
C20 C 0.7444(3) 0.9324(3) 0.3764(2) 0.0502(9) Uani 1 1 d . . . . .
H20 H 0.6792 0.9455 0.3963 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7351(3) 0.9486(3) 0.29472(18) 0.0382(8) Uani 1 1 d . . . . .
H21 H 0.6631 0.9710 0.2596 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7317(2) 0.5986(3) 0.15173(16) 0.0287(7) Uani 1 1 d . . . . .
C23 C 0.6603(3) 0.6031(3) 0.20520(18) 0.0364(8) Uani 1 1 d . . . . .
H23 H 0.6480 0.6803 0.2284 0.044 Uiso 1 1 calc R U . . .
C24 C 0.6077(3) 0.4934(3) 0.22378(19) 0.0417(8) Uani 1 1 d . . . . .
H24 H 0.5608 0.4984 0.2597 0.050 Uiso 1 1 calc R U . . .
C25 C 0.6230(3) 0.3767(3) 0.19044(18) 0.0372(8) Uani 1 1 d . . . . .
C26 C 0.6936(3) 0.3727(3) 0.13687(19) 0.0399(8) Uani 1 1 d . . . . .
H26 H 0.7055 0.2954 0.1135 0.048 Uiso 1 1 calc R U . . .
C27 C 0.7462(3) 0.4813(3) 0.11798(17) 0.0357(7) Uani 1 1 d . . . . .
H27 H 0.7926 0.4761 0.0818 0.043 Uiso 1 1 calc R U . . .
C28 C 0.5664(3) 0.2582(3) 0.2121(2) 0.0542(10) Uani 1 1 d . . . . .
H28A H 0.5903 0.2463 0.2700 0.081 Uiso 1 1 calc R U . . .
H28B H 0.5904 0.1859 0.1860 0.081 Uiso 1 1 calc R U . . .
H28C H 0.4824 0.2668 0.1943 0.081 Uiso 1 1 calc R U . . .


_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
O2 C2 1.225(4) . ?
N1 C2 1.373(4) . ?
N1 C4 1.425(3) . ?
N1 C8 1.482(3) . ?
C2 C3 1.506(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.338(4) . ?
C4 C22 1.472(4) . ?
C5 C6 1.450(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(4) . ?
C6 C9 1.459(4) . ?
C7 C15 1.489(4) . ?
C7 C8 1.496(4) . ?
C8 C16 1.526(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.376(4) . ?
C9 C14 1.407(4) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.504(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.383(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.392(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.388(4) . ?
C22 C23 1.398(4) . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(4) . ?
C25 C28 1.503(4) . ?
C26 C27 1.377(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 125.4(2) . . ?
C2 N1 C8 118.1(2) . . ?
C4 N1 C8 116.3(2) . . ?
O2 C2 N1 120.7(3) . . ?
O2 C2 C3 120.5(3) . . ?
N1 C2 C3 118.7(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N1 117.9(3) . . ?
C5 C4 C22 122.8(3) . . ?
N1 C4 C22 118.8(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 C9 110.0(3) . . ?
C5 C6 C9 130.6(3) . . ?
C6 C7 C15 110.5(2) . . ?
C6 C7 C8 120.0(3) . . ?
C15 C7 C8 129.6(3) . . ?
N1 C8 C7 107.5(2) . . ?
N1 C8 C16 109.1(2) . . ?
C7 C8 C16 115.6(2) . . ?
N1 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C16 C8 H8 108.1 . . ?
C10 C9 C14 120.7(3) . . ?
C10 C9 C6 131.7(3) . . ?
C14 C9 C6 107.6(2) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 119.4(3) . . ?
C13 C14 C15 131.9(3) . . ?
C9 C14 C15 108.7(2) . . ?
C7 C15 C14 103.3(2) . . ?
C7 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C7 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 C21 119.0(3) . . ?
C17 C16 C8 122.3(3) . . ?
C21 C16 C8 118.4(3) . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C27 C22 C23 117.6(3) . . ?
C27 C22 C4 121.7(2) . . ?
C23 C22 C4 120.6(3) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 121.8(3) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 117.6(3) . . ?
C24 C25 C28 121.1(3) . . ?
C26 C25 C28 121.3(3) . . ?
C27 C26 C25 121.0(3) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C22 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane-Hexane'
_chemical_compound_source        NO
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1452927'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1-(2,4-diphenyl-6-(p-tolyl)pyridin-1(2H)-yl)ethanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O'
_chemical_formula_sum            'C26 H23 N O'
_chemical_formula_weight         365.45

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   12.523(13)
_cell_length_b                   9.952(10)
_cell_length_c                   16.598(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.466(16)
_cell_angle_gamma                90
_cell_volume                     1973(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58 
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14243
_diffrn_reflns_av_unetI/netI     0.1885
_diffrn_reflns_av_R_equivalents  0.2392
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.173
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3666
_reflns_number_gt                1507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   0.655
_refine_ls_restrained_S_all      0.655
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O26 O 0.64160(19) 0.3706(2) 0.01122(15) 0.0728(7) Uani 1 1 d . . . . .
N1 N 0.76614(18) 0.2213(2) -0.00905(14) 0.0436(6) Uani 1 1 d . . . . .
C2 C 0.8012(2) 0.0898(3) -0.02050(16) 0.0398(7) Uani 1 1 d . . . . .
C3 C 0.8651(2) 0.0751(3) -0.07200(17) 0.0448(7) Uani 1 1 d . . . . .
H3 H 0.8942 -0.0093 -0.0774 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8902(2) 0.1867(3) -0.11950(18) 0.0425(7) Uani 1 1 d . . . . .
C5 C 0.8809(2) 0.3093(3) -0.08947(19) 0.0496(8) Uani 1 1 d . . . . .
H5 H 0.8969 0.3841 -0.1174 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8456(2) 0.3287(3) -0.01251(18) 0.0459(7) Uani 1 1 d . . . . .
H6 H 0.8044 0.4137 -0.0195 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7766(2) -0.0210(3) 0.03022(17) 0.0412(7) Uani 1 1 d . . . . .
C8 C 0.7851(2) -0.0051(3) 0.11407(18) 0.0496(8) Uani 1 1 d . . . . .
H8 H 0.8048 0.0783 0.1395 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7652(3) -0.1103(3) 0.1609(2) 0.0565(8) Uani 1 1 d . . . . .
H9 H 0.7718 -0.0969 0.2176 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7356(2) -0.2356(3) 0.1258(2) 0.0517(8) Uani 1 1 d . . . . .
C11 C 0.7273(2) -0.2511(3) 0.0421(2) 0.0528(8) Uani 1 1 d . . . . .
H11 H 0.7080 -0.3348 0.0169 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7467(2) -0.1460(3) -0.00570(19) 0.0500(8) Uani 1 1 d . . . . .
H12 H 0.7397 -0.1593 -0.0625 0.060 Uiso 1 1 calc R U . . .
C13 C 0.7139(3) -0.3502(3) 0.1774(2) 0.0775(12) Uani 1 1 d . . . . .
H13A H 0.7014 -0.4308 0.1441 0.116 Uiso 1 1 calc R U . . .
H13B H 0.6490 -0.3308 0.1947 0.116 Uiso 1 1 calc R U . . .
H13C H 0.7775 -0.3623 0.2264 0.116 Uiso 1 1 calc R U . . .
C14 C 0.9228(2) 0.1598(3) -0.19665(18) 0.0469(8) Uani 1 1 d . . . . .
C15 C 0.9070(3) 0.0347(3) -0.2351(2) 0.0590(9) Uani 1 1 d . . . . .
H15 H 0.8789 -0.0355 -0.2105 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9321(3) 0.0129(4) -0.3088(2) 0.0723(10) Uani 1 1 d . . . . .
H16 H 0.9204 -0.0720 -0.3332 0.087 Uiso 1 1 calc R U . . .
C17 C 0.9735(3) 0.1114(5) -0.3472(2) 0.0739(11) Uani 1 1 d . . . . .
H17 H 0.9906 0.0950 -0.3971 0.089 Uiso 1 1 calc R U . . .
C18 C 0.9895(3) 0.2357(4) -0.3104(2) 0.0763(11) Uani 1 1 d . . . . .
H18 H 1.0173 0.3050 -0.3359 0.092 Uiso 1 1 calc R U . . .
C19 C 0.9651(3) 0.2595(4) -0.2366(2) 0.0666(10) Uani 1 1 d . . . . .
H19 H 0.9772 0.3448 -0.2127 0.080 Uiso 1 1 calc R U . . .
C20 C 0.9376(3) 0.3367(3) 0.07070(19) 0.0467(8) Uani 1 1 d . . . . .
C21 C 1.0496(3) 0.3226(3) 0.0768(2) 0.0569(9) Uani 1 1 d . . . . .
H21 H 1.0705 0.3075 0.0283 0.068 Uiso 1 1 calc R U . . .
C22 C 1.1307(3) 0.3306(3) 0.1542(2) 0.0682(10) Uani 1 1 d . . . . .
H22 H 1.2058 0.3219 0.1574 0.082 Uiso 1 1 calc R U . . .
C23 C 1.1017(3) 0.3511(3) 0.2260(2) 0.0700(10) Uani 1 1 d . . . . .
H23 H 1.1567 0.3551 0.2780 0.084 Uiso 1 1 calc R U . . .
C24 C 0.9914(3) 0.3657(4) 0.2215(2) 0.0723(10) Uani 1 1 d . . . . .
H24 H 0.9710 0.3804 0.2702 0.087 Uiso 1 1 calc R U . . .
C25 C 0.9104(3) 0.3583(3) 0.1438(2) 0.0607(9) Uani 1 1 d . . . . .
H25 H 0.8356 0.3682 0.1411 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6604(2) 0.2563(3) -0.00616(19) 0.0523(8) Uani 1 1 d . . . . .
C27 C 0.5719(3) 0.1509(4) -0.0248(2) 0.0702(10) Uani 1 1 d . . . . .
H27A H 0.4998 0.1922 -0.0477 0.105 Uiso 1 1 calc R U . . .
H27B H 0.5743 0.1042 0.0264 0.105 Uiso 1 1 calc R U . . .
H27C H 0.5845 0.0884 -0.0650 0.105 Uiso 1 1 calc R U . . .


_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
O26 C26 1.213(4) . ?
N1 C26 1.384(4) . ?
N1 C2 1.411(4) . ?
N1 C6 1.474(4) . ?
C2 C3 1.343(4) . ?
C2 C7 1.475(4) . ?
C3 C4 1.451(4) . ?
C4 C5 1.336(4) . ?
C4 C14 1.480(4) . ?
C5 C6 1.484(4) . ?
C6 C20 1.511(4) . ?
C7 C8 1.372(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.371(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.371(4) . ?
C10 C13 1.499(4) . ?
C11 C12 1.378(4) . ?
C14 C19 1.384(4) . ?
C14 C15 1.387(4) . ?
C15 C16 1.368(4) . ?
C16 C17 1.354(5) . ?
C17 C18 1.366(5) . ?
C18 C19 1.369(5) . ?
C20 C25 1.372(4) . ?
C20 C21 1.383(4) . ?
C21 C22 1.381(5) . ?
C22 C23 1.361(5) . ?
C23 C24 1.369(5) . ?
C24 C25 1.382(5) . ?
C26 C27 1.490(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 N1 C2 125.3(2) . . ?
C26 N1 C6 118.9(2) . . ?
C2 N1 C6 115.3(2) . . ?
C3 C2 N1 117.1(2) . . ?
C3 C2 C7 123.3(3) . . ?
N1 C2 C7 119.3(2) . . ?
C2 C3 C4 122.0(3) . . ?
C5 C4 C3 116.1(3) . . ?
C5 C4 C14 124.4(3) . . ?
C3 C4 C14 119.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
N1 C6 C5 108.6(2) . . ?
N1 C6 C20 109.9(2) . . ?
C5 C6 C20 116.8(3) . . ?
C8 C7 C12 118.0(3) . . ?
C8 C7 C2 121.8(3) . . ?
C12 C7 C2 120.2(3) . . ?
C7 C8 C9 121.0(3) . . ?
C8 C9 C10 121.5(3) . . ?
C11 C10 C9 117.3(3) . . ?
C11 C10 C13 121.5(3) . . ?
C9 C10 C13 121.2(3) . . ?
C10 C11 C12 121.7(3) . . ?
C11 C12 C7 120.5(3) . . ?
C19 C14 C15 116.4(3) . . ?
C19 C14 C4 122.0(3) . . ?
C15 C14 C4 121.5(3) . . ?
C16 C15 C14 121.0(3) . . ?
C17 C16 C15 121.9(4) . . ?
C16 C17 C18 118.1(3) . . ?
C17 C18 C19 120.9(4) . . ?
C18 C19 C14 121.7(4) . . ?
C25 C20 C21 117.8(3) . . ?
C25 C20 C6 119.6(3) . . ?
C21 C20 C6 122.6(3) . . ?
C20 C21 C22 120.6(3) . . ?
C23 C22 C21 120.6(3) . . ?
C22 C23 C24 119.9(3) . . ?
C23 C24 C25 119.4(3) . . ?
C20 C25 C24 121.8(3) . . ?
O26 C26 N1 120.0(3) . . ?
O26 C26 C27 121.6(3) . . ?
N1 C26 C27 118.4(3) . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.083

# start Validation Reply Form
_vrf_PLAT020_shelx               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.239 Report
RESPONSE: The overall quality of the data was poor due to the crystal quality
;
# end Validation Reply Form


_shelxl_version_number           2013-4



