# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_yangxl1015_twin1_hklf4
_audit_block_doi                 10.5517/cc145fk9
_database_code_depnum_ccdc_archive 'CCDC 1047910'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_audit_creation_date             2014-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H25 N3 O2'
_chemical_formula_sum            'C24 H25 N3 O2'
_chemical_formula_weight         387.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.1121(7)
_cell_length_b                   8.5933(10)
_cell_length_c                   18.426(2)
_cell_angle_alpha                94.339(10)
_cell_angle_beta                 100.719(10)
_cell_angle_gamma                105.418(10)
_cell_volume                     1057.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1013
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4810
_cell_measurement_theta_min      3.9510
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4555
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.2008  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   55.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -57.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   50.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   63.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   12.00   45.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega    4.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   57.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  9 omega  -20.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -99.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega  -31.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -38.0000   60.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0337897000
_diffrn_orient_matrix_UB_12      -0.0831725000
_diffrn_orient_matrix_UB_13      -0.0156005000
_diffrn_orient_matrix_UB_21      0.0098935000
_diffrn_orient_matrix_UB_22      -0.0233139000
_diffrn_orient_matrix_UB_23      0.0363144000
_diffrn_orient_matrix_UB_31      -0.0998950000
_diffrn_orient_matrix_UB_32      -0.0003444000
_diffrn_orient_matrix_UB_33      -0.0001117000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.8907 1472 8298
2 0.1093 0 8298

_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1955
_reflns_number_total             4555
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      0.850
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1338
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.9918(3) 0.5706(3) 0.39807(12) 0.0925(8) Uani 1 d . . .
O2 O 0.5353(3) 0.3122(2) 0.19359(11) 0.0604(6) Uani 1 d . . .
N1 N 0.8448(3) 0.7530(3) 0.44301(13) 0.0543(7) Uani 1 d . . .
N2 N 0.3777(3) 0.1752(3) 0.15701(13) 0.0578(7) Uani 1 d . . .
N3 N -0.6516(4) -0.3812(3) -0.01038(17) 0.0811(9) Uani 1 d . . .
C1 C 0.7824(4) 0.8846(3) 0.41817(16) 0.0479(7) Uani 1 d . . .
C2 C 0.7059(4) 0.9885(4) 0.45561(18) 0.0671(9) Uani 1 d . . .
H2 H 0.6881 0.9772 0.5039 0.080 Uiso 1 calc . . R
C3 C 0.6555(5) 1.1125(4) 0.4181(2) 0.0792(10) Uani 1 d . . .
H3 H 0.6056 1.1863 0.4425 0.095 Uiso 1 calc . . R
C4 C 0.6778(5) 1.1278(4) 0.3468(2) 0.0785(10) Uani 1 d . . .
H4 H 0.6401 1.2090 0.3224 0.094 Uiso 1 calc . . R
C5 C 0.7571(4) 1.0210(4) 0.31140(17) 0.0635(9) Uani 1 d . . .
H5 H 0.7733 1.0311 0.2629 0.076 Uiso 1 calc . . R
C6 C 0.8121(4) 0.9008(3) 0.34671(16) 0.0479(7) Uani 1 d . . .
C7 C 0.9095(4) 0.7770(3) 0.32359(15) 0.0504(8) Uani 1 d . . .
C8 C 0.9228(4) 0.6863(4) 0.39125(18) 0.0588(8) Uani 1 d . . .
C9 C 1.1193(4) 0.8538(4) 0.31072(17) 0.0767(10) Uani 1 d . . .
H9A H 1.1093 0.9059 0.2664 0.115 Uiso 1 calc . . GR
H9B H 1.1846 0.7707 0.3050 0.115 Uiso 1 calc . . GR
H9C H 1.1952 0.9331 0.3526 0.115 Uiso 1 calc . . GR
C10 C 0.7862(4) 0.6555(3) 0.25508(15) 0.0570(8) Uani 1 d . . .
H10A H 0.7843 0.7120 0.2114 0.068 Uiso 1 calc . . R
H10B H 0.8517 0.5715 0.2481 0.068 Uiso 1 calc . . R
C11 C 0.8249(5) 0.6937(4) 0.51350(17) 0.0801(10) Uani 1 d . . .
H11A H 0.8826 0.7823 0.5532 0.120 Uiso 1 calc . . GR
H11B H 0.8928 0.6115 0.5207 0.120 Uiso 1 calc . . GR
H11C H 0.6860 0.6481 0.5133 0.120 Uiso 1 calc . . GR
C12 C 0.5723(4) 0.5749(3) 0.26043(15) 0.0549(8) Uani 1 d . . .
H12A H 0.5740 0.5233 0.3055 0.066 Uiso 1 calc . . R
H12B H 0.5047 0.6583 0.2647 0.066 Uiso 1 calc . . R
C13 C 0.4551(4) 0.4496(3) 0.19501(15) 0.0487(7) Uani 1 d . . .
H13 H 0.4712 0.4993 0.1496 0.058 Uiso 1 calc . . R
C14 C 0.2329(4) 0.3763(3) 0.18993(14) 0.0433(7) Uani 1 d . . .
C15 C 0.2113(4) 0.2076(3) 0.15221(13) 0.0412(7) Uani 1 d . . .
C16 C 0.1190(4) 0.4781(3) 0.14512(16) 0.0653(9) Uani 1 d . . .
H16A H 0.1340 0.4671 0.0944 0.098 Uiso 1 calc . . GR
H16B H 0.1716 0.5904 0.1664 0.098 Uiso 1 calc . . GR
H16C H -0.0199 0.4406 0.1464 0.098 Uiso 1 calc . . GR
C17 C 0.1754(4) 0.3592(3) 0.26557(15) 0.0605(8) Uani 1 d . . .
H17A H 0.0351 0.3056 0.2581 0.091 Uiso 1 calc . . GR
H17B H 0.2054 0.4653 0.2932 0.091 Uiso 1 calc . . GR
H17C H 0.2497 0.2960 0.2928 0.091 Uiso 1 calc . . GR
C18 C 0.0271(4) 0.0780(3) 0.11835(13) 0.0404(7) Uani 1 d . . .
C19 C -0.1597(4) 0.1003(3) 0.11564(15) 0.0495(8) Uani 1 d . . .
H19 H -0.1690 0.1994 0.1364 0.059 Uiso 1 calc . . R
C20 C -0.3308(4) -0.0194(3) 0.08323(15) 0.0522(8) Uani 1 d . . .
H20 H -0.4545 -0.0013 0.0821 0.063 Uiso 1 calc . . R
C21 C -0.3203(4) -0.1660(3) 0.05247(14) 0.0447(7) Uani 1 d . . .
C22 C -0.1362(4) -0.1938(3) 0.05547(15) 0.0511(8) Uani 1 d . . .
H22 H -0.1281 -0.2940 0.0356 0.061 Uiso 1 calc . . R
C23 C 0.0340(4) -0.0726(3) 0.08796(15) 0.0488(7) Uani 1 d . . .
H23 H 0.1574 -0.0917 0.0897 0.059 Uiso 1 calc . . R
C24 C -0.5032(5) -0.2879(4) 0.01738(17) 0.0573(9) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.225(3) . ?
O2 N2 1.412(3) . ?
O2 C13 1.442(3) . ?
N1 C1 1.399(3) . ?
N1 C8 1.353(3) . ?
N1 C11 1.448(3) . ?
N2 C15 1.276(3) . ?
N3 C24 1.143(3) . ?
C1 C2 1.368(4) . ?
C1 C6 1.383(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(4) . ?
C6 C7 1.492(3) . ?
C7 C8 1.521(4) . ?
C7 C9 1.533(3) . ?
C7 C10 1.535(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C12 1.520(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.503(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.520(3) . ?
C14 C15 1.516(3) . ?
C14 C16 1.529(3) . ?
C14 C17 1.530(4) . ?
C15 C18 1.470(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.384(3) . ?
C18 C23 1.388(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.368(3) . ?
C21 C22 1.384(3) . ?
C21 C24 1.438(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.369(3) . ?
C23 H23 0.9300 . ?

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
N2 O2 C13 107.10(17) . . ?
C1 N1 C11 124.9(3) . . ?
C8 N1 C1 110.5(2) . . ?
C8 N1 C11 124.6(2) . . ?
C15 N2 O2 109.8(2) . . ?
C2 C1 N1 128.3(3) . . ?
C2 C1 C6 122.2(3) . . ?
C6 C1 N1 109.5(2) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 109.2(2) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 131.8(3) . . ?
C6 C7 C8 101.6(2) . . ?
C6 C7 C9 112.7(2) . . ?
C6 C7 C10 114.3(2) . . ?
C8 C7 C9 109.9(2) . . ?
C8 C7 C10 108.7(2) . . ?
C9 C7 C10 109.2(2) . . ?
O1 C8 N1 125.0(3) . . ?
O1 C8 C7 125.8(3) . . ?
N1 C8 C7 109.1(2) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 108.7 . . ?
C7 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C10 C7 114.0(2) . . ?
C12 C10 H10A 108.7 . . ?
C12 C10 H10B 108.7 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 108.8 . . ?
C10 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C10 113.9(2) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
O2 C13 C12 110.1(2) . . ?
O2 C13 H13 107.7 . . ?
O2 C13 C14 104.9(2) . . ?
C12 C13 H13 107.7 . . ?
C12 C13 C14 118.3(2) . . ?
C14 C13 H13 107.7 . . ?
C13 C14 C16 108.8(2) . . ?
C13 C14 C17 114.0(2) . . ?
C15 C14 C13 98.37(19) . . ?
C15 C14 C16 116.1(2) . . ?
C15 C14 C17 108.2(2) . . ?
C16 C14 C17 111.0(2) . . ?
N2 C15 C14 113.0(2) . . ?
N2 C15 C18 118.3(2) . . ?
C18 C15 C14 128.4(2) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 121.7(2) . . ?
C19 C18 C23 117.3(2) . . ?
C23 C18 C15 121.0(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.7(2) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 C24 118.5(2) . . ?
C22 C21 C24 121.6(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C18 C23 H23 119.2 . . ?
C22 C23 C18 121.7(2) . . ?
C22 C23 H23 119.2 . . ?
N3 C24 C21 177.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N2 C15 C14 -2.9(3) . . . . ?
O2 N2 C15 C18 -177.6(2) . . . . ?
O2 C13 C14 C15 -24.4(2) . . . . ?
O2 C13 C14 C16 -145.6(2) . . . . ?
O2 C13 C14 C17 89.9(3) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
N1 C1 C6 C5 178.8(2) . . . . ?
N1 C1 C6 C7 -2.8(3) . . . . ?
N2 O2 C13 C12 153.2(2) . . . . ?
N2 O2 C13 C14 24.9(3) . . . . ?
N2 C15 C18 C19 175.6(2) . . . . ?
N2 C15 C18 C23 -4.1(4) . . . . ?
C1 N1 C8 O1 179.0(3) . . . . ?
C1 N1 C8 C7 -1.4(3) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C1 C6 C7 C8 1.9(3) . . . . ?
C1 C6 C7 C9 -115.7(3) . . . . ?
C1 C6 C7 C10 118.8(3) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?
C2 C1 C6 C7 176.2(2) . . . . ?
C2 C3 C4 C5 -1.8(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -176.3(3) . . . . ?
C5 C6 C7 C8 -180.0(3) . . . . ?
C5 C6 C7 C9 62.4(4) . . . . ?
C5 C6 C7 C10 -63.1(4) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C7 C8 O1 179.3(3) . . . . ?
C6 C7 C8 N1 -0.3(3) . . . . ?
C6 C7 C10 C12 -50.9(3) . . . . ?
C7 C10 C12 C13 -177.0(2) . . . . ?
C8 N1 C1 C2 -176.3(3) . . . . ?
C8 N1 C1 C6 2.7(3) . . . . ?
C8 C7 C10 C12 61.8(3) . . . . ?
C9 C7 C8 O1 -61.1(4) . . . . ?
C9 C7 C8 N1 119.3(2) . . . . ?
C9 C7 C10 C12 -178.3(2) . . . . ?
C10 C7 C8 O1 58.4(4) . . . . ?
C10 C7 C8 N1 -121.2(2) . . . . ?
C10 C12 C13 O2 66.9(3) . . . . ?
C10 C12 C13 C14 -172.7(2) . . . . ?
C11 N1 C1 C2 5.0(4) . . . . ?
C11 N1 C1 C6 -176.1(3) . . . . ?
C11 N1 C8 O1 -2.2(5) . . . . ?
C11 N1 C8 C7 177.4(2) . . . . ?
C12 C13 C14 C15 -147.4(2) . . . . ?
C12 C13 C14 C16 91.3(3) . . . . ?
C12 C13 C14 C17 -33.2(3) . . . . ?
C13 O2 N2 C15 -14.3(3) . . . . ?
C13 C14 C15 N2 17.4(3) . . . . ?
C13 C14 C15 C18 -168.5(2) . . . . ?
C14 C15 C18 C19 1.8(4) . . . . ?
C14 C15 C18 C23 -177.9(3) . . . . ?
C15 C18 C19 C20 179.1(3) . . . . ?
C15 C18 C23 C22 -179.2(2) . . . . ?
C16 C14 C15 N2 133.2(3) . . . . ?
C16 C14 C15 C18 -52.8(4) . . . . ?
C17 C14 C15 N2 -101.3(3) . . . . ?
C17 C14 C15 C18 72.8(3) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C18 C23 C22 1.0(4) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C19 C20 C21 C24 -178.6(3) . . . . ?
C20 C21 C22 C23 -1.4(4) . . . . ?
C20 C21 C24 N3 12(10) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C22 C21 C24 N3 -168(10) . . . . ?
C23 C18 C19 C20 -1.2(4) . . . . ?
C24 C21 C22 C23 178.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yangxl0120
_audit_block_doi                 10.5517/cc145fnd
_database_code_depnum_ccdc_archive 'CCDC 1047913'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;
_audit_creation_date             2015-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_chemical_name_common            ?
_chemical_name_systematic        
3-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
_chemical_formula_moiety         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51
_chemical_melting_point          427-428
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.8733(11)
_cell_length_b                   11.8466(6)
_cell_length_c                   12.3385(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.402(6)
_cell_angle_gamma                90.00
_cell_volume                     2289.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1254
_cell_measurement_temperature    293.69(10)
_cell_measurement_theta_max      22.5840
_cell_measurement_theta_min      3.7750
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8698
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   14.60   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -90.0000 23

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00   90.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   64.40   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  150.0000 97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0423080000
_diffrn_orient_matrix_UB_12      0.0074089000
_diffrn_orient_matrix_UB_13      0.0281885000
_diffrn_orient_matrix_UB_21      -0.0161983000
_diffrn_orient_matrix_UB_22      0.0174438000
_diffrn_orient_matrix_UB_23      0.0475881000
_diffrn_orient_matrix_UB_31      0.0005502000
_diffrn_orient_matrix_UB_32      -0.0568001000
_diffrn_orient_matrix_UB_33      0.0182743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2326
_reflns_number_total             4502
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0485P)²+0.4541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1683
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.27093(14) 0.49719(17) 0.01256(19) 0.0705(7) Uani 1 d . . .
O2 O 0.08529(14) 0.75135(18) 0.02174(18) 0.0626(6) Uani 1 d . . .
O3 O -0.18159(15) 0.4284(2) 0.3212(2) 0.0887(8) Uani 1 d . . .
N1 N 0.32364(18) 0.4778(2) -0.0684(2) 0.0683(8) Uani 1 d . . .
N2 N 0.01272(15) 0.6392(2) 0.1271(2) 0.0508(7) Uani 1 d . . .
C1 C 0.4980(2) 0.6288(3) -0.1493(3) 0.0690(10) Uani 1 d . . .
H1 H 0.5123 0.6734 -0.0870 0.083 Uiso 1 calc . . R
C2 C 0.5522(2) 0.6241(3) -0.2259(4) 0.0815(12) Uani 1 d . . .
H2 H 0.6025 0.6658 -0.2152 0.098 Uiso 1 calc . . R
C3 C 0.5322(2) 0.5586(3) -0.3173(4) 0.0807(12) Uani 1 d . . .
H3 H 0.5695 0.5544 -0.3680 0.097 Uiso 1 calc . . R
C4 C 0.4571(3) 0.4987(3) -0.3346(3) 0.0808(11) Uani 1 d . . .
H4 H 0.4432 0.4543 -0.3971 0.097 Uiso 1 calc . . R
C5 C 0.4023(2) 0.5046(3) -0.2586(3) 0.0655(10) Uani 1 d . . .
H5 H 0.3509 0.4653 -0.2714 0.079 Uiso 1 calc . . R
C6 C 0.42236(18) 0.5677(3) -0.1640(3) 0.0512(8) Uani 1 d . . .
C7 C 0.36497(17) 0.5680(2) -0.0806(2) 0.0480(8) Uani 1 d . . .
C8 C 0.34897(17) 0.6629(2) -0.0044(3) 0.0435(7) Uani 1 d . . .
C9 C 0.26593(17) 0.6175(2) 0.0260(2) 0.0492(8) Uani 1 d . . .
H9 H 0.2184 0.6459 -0.0279 0.059 Uiso 1 calc . . R
C10 C 0.42106(19) 0.6691(3) 0.0940(3) 0.0648(10) Uani 1 d . . .
H10A H 0.4069 0.7237 0.1457 0.097 Uiso 1 calc . . GR
H10B H 0.4731 0.6910 0.0695 0.097 Uiso 1 calc . . GR
H10C H 0.4285 0.5964 0.1288 0.097 Uiso 1 calc . . GR
C11 C 0.3349(2) 0.7775(3) -0.0608(3) 0.0745(11) Uani 1 d . . .
H11A H 0.2915 0.7709 -0.1245 0.112 Uiso 1 calc . . GR
H11B H 0.3872 0.8024 -0.0827 0.112 Uiso 1 calc . . GR
H11C H 0.3172 0.8312 -0.0108 0.112 Uiso 1 calc . . GR
C12 C 0.24724(17) 0.6437(2) 0.1395(2) 0.0481(8) Uani 1 d . . .
H12A H 0.2865 0.6013 0.1929 0.058 Uiso 1 calc . . R
H12B H 0.2577 0.7233 0.1545 0.058 Uiso 1 calc . . R
C13 C 0.15778(17) 0.6166(2) 0.1545(2) 0.0441(7) Uani 1 d . . .
C14 C 0.08387(19) 0.6786(3) 0.0920(3) 0.0490(8) Uani 1 d . . .
C15 C 0.03204(17) 0.5527(2) 0.2121(2) 0.0418(7) Uani 1 d . . .
C16 C 0.12933(16) 0.5446(2) 0.2225(2) 0.0409(7) Uani 1 d . . .
C17 C -0.07203(19) 0.6835(3) 0.0902(3) 0.0694(10) Uani 1 d . . .
H17A H -0.1109 0.6221 0.0699 0.104 Uiso 1 calc . . GR
H17B H -0.0712 0.7316 0.0278 0.104 Uiso 1 calc . . GR
H17C H -0.0902 0.7260 0.1484 0.104 Uiso 1 calc . . GR
C18 C 0.17895(16) 0.4617(2) 0.2979(2) 0.0406(7) Uani 1 d . . .
C19 C 0.19191(18) 0.4760(3) 0.4105(3) 0.0509(8) Uani 1 d . . .
H19 H 0.1693 0.5387 0.4409 0.061 Uiso 1 calc . . R
C20 C 0.23870(19) 0.3970(3) 0.4784(3) 0.0629(9) Uani 1 d . . .
H20 H 0.2479 0.4078 0.5540 0.075 Uiso 1 calc . . R
C21 C 0.27126(19) 0.3037(3) 0.4354(4) 0.0681(11) Uani 1 d . . .
H21 H 0.3020 0.2509 0.4817 0.082 Uiso 1 calc . . R
C22 C 0.25854(19) 0.2881(3) 0.3237(4) 0.0670(10) Uani 1 d . . .
H22 H 0.2804 0.2244 0.2941 0.080 Uiso 1 calc . . R
C23 C 0.21331(18) 0.3671(2) 0.2553(3) 0.0560(9) Uani 1 d . . .
H23 H 0.2058 0.3568 0.1796 0.067 Uiso 1 calc . . R
C24 C 0.00366(18) 0.5927(2) 0.3163(2) 0.0491(8) Uani 1 d . . .
H24 H 0.0338 0.6511 0.3554 0.059 Uiso 1 calc . . R
C25 C -0.1123(2) 0.4564(3) 0.2979(3) 0.0581(9) Uani 1 d . . .
C26 C -0.06165(19) 0.5491(3) 0.3545(3) 0.0571(9) Uani 1 d . . .
H26 H -0.0762 0.5777 0.4191 0.069 Uiso 1 calc . . R
C27 C -0.07696(19) 0.4017(3) 0.2104(3) 0.0570(9) Uani 1 d . . .
H27 H -0.1013 0.3348 0.1810 0.068 Uiso 1 calc . . R
C28 C -0.01099(18) 0.4442(2) 0.1709(3) 0.0519(8) Uani 1 d . . .
H28 H 0.0096 0.4053 0.1152 0.062 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.422(3) . ?
O1 C9 1.439(3) . ?
O2 C14 1.225(3) . ?
O3 C25 1.227(3) . ?
N1 C7 1.275(3) . ?
N2 C14 1.357(3) . ?
N2 C15 1.463(4) . ?
N2 C17 1.446(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 C7 1.482(4) . ?
C7 C8 1.514(4) . ?
C8 C9 1.526(3) . ?
C8 C10 1.528(4) . ?
C8 C11 1.525(4) . ?
C9 H9 0.9800 . ?
C9 C12 1.511(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.496(4) . ?
C13 C14 1.488(4) . ?
C13 C16 1.326(4) . ?
C15 C16 1.532(3) . ?
C15 C24 1.506(4) . ?
C15 C28 1.504(4) . ?
C16 C18 1.487(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.382(4) . ?
C18 C23 1.387(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C26 1.313(4) . ?
C25 C26 1.469(4) . ?
C25 C27 1.449(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.325(4) . ?
C28 H28 0.9300 . ?

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 O1 C9 106.91(19) . . ?
C7 N1 O1 108.7(2) . . ?
C14 N2 C15 112.5(2) . . ?
C14 N2 C17 123.7(3) . . ?
C17 N2 C15 123.7(2) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.7(3) . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 120.4(3) . . ?
N1 C7 C6 117.8(3) . . ?
N1 C7 C8 114.0(2) . . ?
C6 C7 C8 128.1(2) . . ?
C7 C8 C9 97.5(2) . . ?
C7 C8 C10 110.4(2) . . ?
C7 C8 C11 113.9(3) . . ?
C9 C8 C10 112.7(2) . . ?
C11 C8 C9 110.9(2) . . ?
C11 C8 C10 110.8(3) . . ?
O1 C9 C8 104.7(2) . . ?
O1 C9 H9 108.2 . . ?
O1 C9 C12 109.5(2) . . ?
C8 C9 H9 108.2 . . ?
C12 C9 C8 117.6(2) . . ?
C12 C9 H9 108.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 108.8 . . ?
C9 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 C9 113.9(2) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C14 C13 C12 120.9(3) . . ?
C16 C13 C12 130.1(3) . . ?
C16 C13 C14 108.9(2) . . ?
O2 C14 N2 125.5(3) . . ?
O2 C14 C13 127.6(3) . . ?
N2 C14 C13 106.9(3) . . ?
N2 C15 C16 101.2(2) . . ?
N2 C15 C24 109.6(2) . . ?
N2 C15 C28 109.0(2) . . ?
C24 C15 C16 112.7(2) . . ?
C28 C15 C16 111.8(2) . . ?
C28 C15 C24 112.0(2) . . ?
C13 C16 C15 110.5(2) . . ?
C13 C16 C18 128.3(2) . . ?
C18 C16 C15 121.1(2) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C16 121.7(3) . . ?
C19 C18 C23 118.5(3) . . ?
C23 C18 C16 119.8(3) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C15 C24 H24 118.4 . . ?
C26 C24 C15 123.1(3) . . ?
C26 C24 H24 118.4 . . ?
O3 C25 C26 122.2(3) . . ?
O3 C25 C27 121.7(3) . . ?
C27 C25 C26 116.1(3) . . ?
C24 C26 C25 121.8(3) . . ?
C24 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C25 C27 H27 119.0 . . ?
C28 C27 C25 122.0(3) . . ?
C28 C27 H27 119.0 . . ?
C15 C28 H28 118.6 . . ?
C27 C28 C15 122.9(3) . . ?
C27 C28 H28 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C7 C6 -178.2(3) . . . . ?
O1 N1 C7 C8 2.5(4) . . . . ?
O1 C9 C12 C13 -72.3(3) . . . . ?
O3 C25 C26 C24 -166.8(3) . . . . ?
O3 C25 C27 C28 167.1(3) . . . . ?
N1 O1 C9 C8 -27.5(3) . . . . ?
N1 O1 C9 C12 -154.5(2) . . . . ?
N1 C7 C8 C9 -18.5(3) . . . . ?
N1 C7 C8 C10 99.2(3) . . . . ?
N1 C7 C8 C11 -135.4(3) . . . . ?
N2 C15 C16 C13 0.7(3) . . . . ?
N2 C15 C16 C18 -177.3(2) . . . . ?
N2 C15 C24 C26 109.6(3) . . . . ?
N2 C15 C28 C27 -109.7(3) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C1 C6 C7 N1 -146.4(3) . . . . ?
C1 C6 C7 C8 32.7(5) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 C7 177.5(3) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C4 C5 C6 C1 2.4(5) . . . . ?
C4 C5 C6 C7 -176.6(3) . . . . ?
C5 C6 C7 N1 32.6(4) . . . . ?
C5 C6 C7 C8 -148.3(3) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C6 C7 C8 C9 162.4(3) . . . . ?
C6 C7 C8 C10 -79.9(4) . . . . ?
C6 C7 C8 C11 45.5(4) . . . . ?
C7 C8 C9 O1 26.4(3) . . . . ?
C7 C8 C9 C12 148.2(3) . . . . ?
C8 C9 C12 C13 168.4(2) . . . . ?
C9 O1 N1 C7 16.2(3) . . . . ?
C9 C12 C13 C14 -65.2(3) . . . . ?
C9 C12 C13 C16 118.4(3) . . . . ?
C10 C8 C9 O1 -89.5(3) . . . . ?
C10 C8 C9 C12 32.3(4) . . . . ?
C11 C8 C9 O1 145.5(3) . . . . ?
C11 C8 C9 C12 -92.7(3) . . . . ?
C12 C13 C14 O2 3.1(5) . . . . ?
C12 C13 C14 N2 -177.1(2) . . . . ?
C12 C13 C16 C15 176.3(3) . . . . ?
C12 C13 C16 C18 -5.9(5) . . . . ?
C13 C16 C18 C19 109.4(3) . . . . ?
C13 C16 C18 C23 -70.8(4) . . . . ?
C14 N2 C15 C16 -0.7(3) . . . . ?
C14 N2 C15 C24 118.6(3) . . . . ?
C14 N2 C15 C28 -118.5(3) . . . . ?
C14 C13 C16 C15 -0.5(3) . . . . ?
C14 C13 C16 C18 177.4(3) . . . . ?
C15 N2 C14 O2 -179.7(3) . . . . ?
C15 N2 C14 C13 0.4(3) . . . . ?
C15 C16 C18 C19 -73.0(3) . . . . ?
C15 C16 C18 C23 106.8(3) . . . . ?
C15 C24 C26 C25 0.3(5) . . . . ?
C16 C13 C14 O2 -179.8(3) . . . . ?
C16 C13 C14 N2 0.0(3) . . . . ?
C16 C15 C24 C26 -138.5(3) . . . . ?
C16 C15 C28 C27 139.3(3) . . . . ?
C16 C18 C19 C20 -179.9(2) . . . . ?
C16 C18 C23 C22 -179.0(3) . . . . ?
C17 N2 C14 O2 -3.9(5) . . . . ?
C17 N2 C14 C13 176.3(3) . . . . ?
C17 N2 C15 C16 -176.5(3) . . . . ?
C17 N2 C15 C24 -57.2(4) . . . . ?
C17 N2 C15 C28 65.6(3) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C18 -1.1(5) . . . . ?
C23 C18 C19 C20 0.3(4) . . . . ?
C24 C15 C16 C13 -116.3(3) . . . . ?
C24 C15 C16 C18 65.8(3) . . . . ?
C24 C15 C28 C27 11.7(4) . . . . ?
C25 C27 C28 C15 -0.7(5) . . . . ?
C26 C25 C27 C28 -11.1(5) . . . . ?
C27 C25 C26 C24 11.3(5) . . . . ?
C28 C15 C16 C13 116.5(3) . . . . ?
C28 C15 C16 C18 -61.5(3) . . . . ?
C28 C15 C24 C26 -11.4(4) . . . . ?

_olex2_date_sample_data_collection 2015-01-22
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether, DCM'
