# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_201307114
_database_code_depnum_ccdc_archive 'CCDC 994843'
_audit_update_record             
;
2014-04-01 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_audit_creation_date             2013-07-09
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H28 N2 O'
_chemical_formula_sum            'C36 H28 N2 O'
_chemical_formula_weight         504.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.4141(9)
_cell_length_b                   11.6808(12)
_cell_length_c                   14.2260(11)
_cell_angle_alpha                104.808(8)
_cell_angle_beta                 91.834(7)
_cell_angle_gamma                113.724(9)
_cell_volume                     1368.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.4883
_cell_measurement_theta_min      3.2493
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9859
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega -105.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega -100.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega  -90.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
  8 omega  -45.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   11.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -19.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   51.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  174.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   52.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 17 omega   58.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
 18 omega   49.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 21 omega   39.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 22 omega   44.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 23 omega   41.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
 24 omega   39.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   66.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
 26 omega   90.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
 28 omega -111.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 29 omega -111.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
 30 omega   26.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0508663000
_diffrn_orient_matrix_UB_12      0.1475630000
_diffrn_orient_matrix_UB_13      0.0169375000
_diffrn_orient_matrix_UB_21      -0.1731482000
_diffrn_orient_matrix_UB_22      -0.0247149000
_diffrn_orient_matrix_UB_23      -0.0205066000
_diffrn_orient_matrix_UB_31      -0.0116689000
_diffrn_orient_matrix_UB_32      0.0182418000
_diffrn_orient_matrix_UB_33      0.1101956000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3649
_reflns_number_total             4861
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.044
_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)+(0.0805P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1545
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C24(H24A,H24B,H24C)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.02494(17) -0.34817(16) 0.43868(11) 0.0674(4) Uani 1 1 d . . .
N1 N 0.16180(18) -0.09753(16) 0.23605(11) 0.0484(4) Uani 1 1 d . . .
N2 N 0.33912(18) 0.05885(16) 0.17195(11) 0.0471(4) Uani 1 1 d . . .
C1 C 0.0406(2) -0.0774(2) 0.27808(15) 0.0538(5) Uani 1 1 d . . .
H1 H -0.0056 -0.0262 0.2626 0.065 Uiso 1 1 calc R . .
C2 C -0.0005(2) -0.1439(2) 0.34550(14) 0.0511(5) Uani 1 1 d . . .
C3 C 0.1016(2) -0.20695(19) 0.34687(13) 0.0466(4) Uani 1 1 d . . .
C4 C 0.2004(2) -0.17711(18) 0.27719(13) 0.0456(4) Uani 1 1 d . . .
C5 C -0.1273(3) -0.1468(3) 0.40828(17) 0.0691(6) Uani 1 1 d . . .
H5A H -0.2143 -0.2316 0.3865 0.104 Uiso 1 1 calc R . .
H5B H -0.1617 -0.0815 0.4026 0.104 Uiso 1 1 calc R . .
H5C H -0.0865 -0.1292 0.4757 0.104 Uiso 1 1 calc R . .
C6 C 0.0989(2) -0.28602(19) 0.41261(13) 0.0500(5) Uani 1 1 d . . .
C7 C 0.2470(2) -0.28794(19) 0.45232(13) 0.0490(4) Uani 1 1 d . . .
C8 C 0.2384(3) -0.4004(2) 0.47266(17) 0.0654(6) Uani 1 1 d . . .
H8 H 0.1426 -0.4732 0.4603 0.078 Uiso 1 1 calc R . .
C9 C 0.3727(4) -0.4037(3) 0.5113(2) 0.0791(7) Uani 1 1 d . . .
H9 H 0.3676 -0.4801 0.5228 0.095 Uiso 1 1 calc R . .
C10 C 0.5137(3) -0.2952(3) 0.5327(2) 0.0790(7) Uani 1 1 d . . .
H10 H 0.6034 -0.2983 0.5589 0.095 Uiso 1 1 calc R . .
C11 C 0.5228(3) -0.1818(3) 0.51585(18) 0.0681(6) Uani 1 1 d . . .
H11 H 0.6177 -0.1074 0.5324 0.082 Uiso 1 1 calc R . .
C12 C 0.3901(2) -0.1791(2) 0.47405(15) 0.0562(5) Uani 1 1 d . . .
H12 H 0.3968 -0.1036 0.4604 0.067 Uiso 1 1 calc R . .
C13 C 0.3192(2) -0.2245(2) 0.24336(14) 0.0502(5) Uani 1 1 d . . .
C14 C 0.2817(3) -0.3570(2) 0.21649(17) 0.0660(6) Uani 1 1 d . . .
H14 H 0.1799 -0.4168 0.2160 0.079 Uiso 1 1 calc R . .
C15 C 0.3959(4) -0.4010(3) 0.1903(2) 0.0895(9) Uani 1 1 d . . .
H15 H 0.3705 -0.4900 0.1726 0.107 Uiso 1 1 calc R . .
C16 C 0.5459(4) -0.3135(4) 0.1904(2) 0.0932(10) Uani 1 1 d . . .
H16 H 0.6219 -0.3435 0.1730 0.112 Uiso 1 1 calc R . .
C17 C 0.5842(3) -0.1827(4) 0.2158(2) 0.0817(8) Uani 1 1 d . . .
H17 H 0.6861 -0.1239 0.2152 0.098 Uiso 1 1 calc R . .
C18 C 0.4718(2) -0.1371(3) 0.24262(16) 0.0606(6) Uani 1 1 d . . .
H18 H 0.4986 -0.0478 0.2601 0.073 Uiso 1 1 calc R . .
C19 C 0.2151(2) -0.05518(19) 0.15161(14) 0.0459(4) Uani 1 1 d . . .
C20 C 0.1291(2) -0.1315(2) 0.05867(14) 0.0484(4) Uani 1 1 d . . .
C21 C 0.1778(2) -0.07897(19) -0.01961(14) 0.0453(4) Uani 1 1 d . . .
C22 C 0.3079(2) 0.0407(2) 0.00158(14) 0.0489(4) Uani 1 1 d . . .
H22 H 0.3426 0.0768 -0.0492 0.059 Uiso 1 1 calc R . .
C23 C 0.3874(2) 0.10788(19) 0.09686(14) 0.0461(4) Uani 1 1 d . . .
C24 C -0.0032(3) -0.2638(2) 0.04534(17) 0.0702(6) Uani 1 1 d . . .
H24A H -0.0982 -0.2542 0.0571 0.105 Uiso 1 1 calc R . .
H24B H 0.0211 -0.3036 0.0910 0.105 Uiso 1 1 calc R . .
H24C H -0.0170 -0.3181 -0.0206 0.105 Uiso 1 1 calc R . .
C25 C 0.0966(2) -0.14438(19) -0.12285(14) 0.0476(4) Uani 1 1 d . . .
C26 C -0.0653(2) -0.1935(2) -0.14722(16) 0.0586(5) Uani 1 1 d . . .
H26 H -0.1264 -0.1882 -0.0976 0.070 Uiso 1 1 calc R . .
C27 C -0.1363(3) -0.2498(2) -0.24388(18) 0.0692(6) Uani 1 1 d . . .
H27 H -0.2448 -0.2826 -0.2588 0.083 Uiso 1 1 calc R . .
C28 C -0.0484(3) -0.2582(2) -0.31859(17) 0.0691(6) Uani 1 1 d . . .
H28 H -0.0969 -0.2965 -0.3838 0.083 Uiso 1 1 calc R . .
C29 C 0.1122(3) -0.2092(3) -0.29589(17) 0.0744(7) Uani 1 1 d . . .
H29 H 0.1726 -0.2144 -0.3459 0.089 Uiso 1 1 calc R . .
C30 C 0.1835(3) -0.1525(2) -0.19907(16) 0.0610(5) Uani 1 1 d . . .
H30 H 0.2921 -0.1189 -0.1847 0.073 Uiso 1 1 calc R . .
C31 C 0.5243(2) 0.2381(2) 0.12195(14) 0.0489(4) Uani 1 1 d . . .
C32 C 0.6048(3) 0.2868(2) 0.05064(17) 0.0654(6) Uani 1 1 d . . .
H32 H 0.5729 0.2376 -0.0152 0.078 Uiso 1 1 calc R . .
C33 C 0.7321(3) 0.4080(3) 0.07651(19) 0.0778(7) Uani 1 1 d . . .
H33 H 0.7842 0.4400 0.0279 0.093 Uiso 1 1 calc R . .
C34 C 0.7821(3) 0.4814(2) 0.1732(2) 0.0744(7) Uani 1 1 d . . .
H34 H 0.8678 0.5627 0.1901 0.089 Uiso 1 1 calc R . .
C35 C 0.7049(3) 0.4341(2) 0.24476(18) 0.0718(7) Uani 1 1 d . . .
H35 H 0.7386 0.4832 0.3105 0.086 Uiso 1 1 calc R . .
C36 C 0.5773(3) 0.3138(2) 0.21918(16) 0.0625(6) Uani 1 1 d . . .
H36 H 0.5257 0.2828 0.2683 0.075 Uiso 1 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 C6 1.228(2) . ?
N1 C1 1.379(2) . ?
N1 C4 1.369(2) . ?
N1 C19 1.443(2) . ?
N2 C19 1.323(2) . ?
N2 C23 1.345(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.355(3) . ?
C2 C3 1.429(3) . ?
C2 C5 1.508(3) . ?
C3 C4 1.394(3) . ?
C3 C6 1.467(3) . ?
C4 C13 1.478(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.499(3) . ?
C7 C8 1.387(3) . ?
C7 C12 1.385(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(3) . ?
C20 C21 1.408(3) . ?
C20 C24 1.504(3) . ?
C21 C22 1.389(3) . ?
C21 C25 1.487(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(3) . ?
C23 C31 1.489(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.391(3) . ?
C25 C30 1.385(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.376(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.380(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.387(3) . ?
C31 C36 1.386(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.370(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.372(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.379(3) . ?
C36 H36 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
C1 N1 C19 121.89(15) . . ?
C4 N1 C1 109.27(16) . . ?
C4 N1 C19 128.14(16) . . ?
C19 N2 C23 117.75(16) . . ?
N1 C1 H1 125.4 . . ?
C2 C1 N1 109.21(18) . . ?
C2 C1 H1 125.4 . . ?
C1 C2 C3 106.82(17) . . ?
C1 C2 C5 125.9(2) . . ?
C3 C2 C5 127.24(19) . . ?
C2 C3 C6 124.07(17) . . ?
C4 C3 C2 107.54(17) . . ?
C4 C3 C6 128.38(18) . . ?
N1 C4 C3 107.15(17) . . ?
N1 C4 C13 122.66(16) . . ?
C3 C4 C13 130.06(17) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 C3 120.10(19) . . ?
O1 C6 C7 118.98(18) . . ?
C3 C6 C7 120.87(16) . . ?
C8 C7 C6 118.61(19) . . ?
C12 C7 C6 122.10(18) . . ?
C12 C7 C8 119.2(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C4 120.19(19) . . ?
C14 C13 C18 118.9(2) . . ?
C18 C13 C4 120.8(2) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
N2 C19 N1 115.05(17) . . ?
N2 C19 C20 126.18(17) . . ?
C20 C19 N1 118.67(17) . . ?
C19 C20 C21 116.03(17) . . ?
C19 C20 C24 120.46(17) . . ?
C21 C20 C24 123.46(18) . . ?
C20 C21 C25 123.43(17) . . ?
C22 C21 C20 117.86(17) . . ?
C22 C21 C25 118.71(16) . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.51(17) . . ?
C23 C22 H22 119.2 . . ?
N2 C23 C22 120.64(17) . . ?
N2 C23 C31 116.77(17) . . ?
C22 C23 C31 122.54(16) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C21 122.29(18) . . ?
C30 C25 C21 119.91(18) . . ?
C30 C25 C26 117.73(19) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.3(2) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(2) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 119.3 . . ?
C29 C30 C25 121.4(2) . . ?
C29 C30 H30 119.3 . . ?
C32 C31 C23 122.08(19) . . ?
C36 C31 C23 120.15(17) . . ?
C36 C31 C32 117.76(19) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 119.7 . . ?
C34 C33 C32 120.6(2) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.6(2) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.0(2) . . ?
C36 C35 H35 120.0 . . ?
C31 C36 H36 119.3 . . ?
C35 C36 C31 121.5(2) . . ?
C35 C36 H36 119.3 . . ?

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
O1 C6 C7 C8 32.7(3) . . . . ?
O1 C6 C7 C12 -143.8(2) . . . . ?
N1 C1 C2 C3 1.0(2) . . . . ?
N1 C1 C2 C5 179.5(2) . . . . ?
N1 C4 C13 C14 -126.4(2) . . . . ?
N1 C4 C13 C18 56.8(3) . . . . ?
N1 C19 C20 C21 174.07(17) . . . . ?
N1 C19 C20 C24 -8.1(3) . . . . ?
N2 C19 C20 C21 -1.9(3) . . . . ?
N2 C19 C20 C24 175.9(2) . . . . ?
N2 C23 C31 C32 166.6(2) . . . . ?
N2 C23 C31 C36 -12.1(3) . . . . ?
C1 N1 C4 C3 -0.3(2) . . . . ?
C1 N1 C4 C13 175.83(18) . . . . ?
C1 N1 C19 N2 96.9(2) . . . . ?
C1 N1 C19 C20 -79.5(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C3 C6 178.03(18) . . . . ?
C2 C3 C4 N1 0.9(2) . . . . ?
C2 C3 C4 C13 -174.85(18) . . . . ?
C2 C3 C6 O1 31.4(3) . . . . ?
C2 C3 C6 C7 -146.02(19) . . . . ?
C3 C4 C13 C14 48.7(3) . . . . ?
C3 C4 C13 C18 -128.1(2) . . . . ?
C3 C6 C7 C8 -149.9(2) . . . . ?
C3 C6 C7 C12 33.6(3) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
C4 N1 C19 N2 -93.7(2) . . . . ?
C4 N1 C19 C20 89.8(2) . . . . ?
C4 C3 C6 O1 -149.6(2) . . . . ?
C4 C3 C6 C7 33.0(3) . . . . ?
C4 C13 C14 C15 -176.2(2) . . . . ?
C4 C13 C18 C17 176.45(19) . . . . ?
C5 C2 C3 C4 -179.7(2) . . . . ?
C5 C2 C3 C6 -0.5(3) . . . . ?
C6 C3 C4 N1 -178.26(18) . . . . ?
C6 C3 C4 C13 6.0(3) . . . . ?
C6 C7 C8 C9 -178.6(2) . . . . ?
C6 C7 C12 C11 176.26(19) . . . . ?
C7 C8 C9 C10 2.2(4) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 -2.1(4) . . . . ?
C10 C11 C12 C7 2.3(4) . . . . ?
C12 C7 C8 C9 -2.0(3) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
C19 N1 C1 C2 170.65(18) . . . . ?
C19 N1 C4 C3 -170.68(18) . . . . ?
C19 N1 C4 C13 5.4(3) . . . . ?
C19 N2 C23 C22 0.6(3) . . . . ?
C19 N2 C23 C31 178.26(17) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C19 C20 C21 C25 -177.76(17) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C20 C21 C25 C26 48.4(3) . . . . ?
C20 C21 C25 C30 -134.7(2) . . . . ?
C21 C22 C23 N2 -0.6(3) . . . . ?
C21 C22 C23 C31 -178.20(18) . . . . ?
C21 C25 C26 C27 177.9(2) . . . . ?
C21 C25 C30 C29 -178.2(2) . . . . ?
C22 C21 C25 C26 -131.1(2) . . . . ?
C22 C21 C25 C30 45.8(3) . . . . ?
C22 C23 C31 C32 -15.7(3) . . . . ?
C22 C23 C31 C36 165.5(2) . . . . ?
C23 N2 C19 N1 -175.36(16) . . . . ?
C23 N2 C19 C20 0.8(3) . . . . ?
C23 C31 C32 C33 -179.7(2) . . . . ?
C23 C31 C36 C35 179.2(2) . . . . ?
C24 C20 C21 C22 -176.0(2) . . . . ?
C24 C20 C21 C25 4.5(3) . . . . ?
C25 C21 C22 C23 178.93(17) . . . . ?
C25 C26 C27 C28 -0.4(4) . . . . ?
C26 C25 C30 C29 -1.1(3) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C28 C29 C30 C25 0.6(4) . . . . ?
C30 C25 C26 C27 1.0(3) . . . . ?
C31 C32 C33 C34 0.8(4) . . . . ?
C32 C31 C36 C35 0.5(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C33 C34 C35 C36 -0.4(4) . . . . ?
C34 C35 C36 C31 0.2(4) . . . . ?
C36 C31 C32 C33 -0.9(4) . . . . ?

####################################################################### 
# 
# 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_20140347
_database_code_depnum_ccdc_archive 'CCDC 994844'
_audit_update_record             
;
2014-04-01 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_audit_creation_date             2014-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C38 H32 N2 O'
_chemical_formula_sum            'C38 H32 N2 O'
_chemical_formula_weight         532.66
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   10.3484(4)
_cell_length_b                   10.5999(4)
_cell_length_c                   27.2911(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2993.62(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.3490
_cell_measurement_theta_min      4.4710
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11308
_diffrn_reflns_theta_full        72.36
_diffrn_reflns_theta_max         72.36
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1312281000
_diffrn_orient_matrix_UB_12      -0.0577636000
_diffrn_orient_matrix_UB_13      0.0145125000
_diffrn_orient_matrix_UB_21      0.0637912000
_diffrn_orient_matrix_UB_22      0.1308667000
_diffrn_orient_matrix_UB_23      -0.0042392000
_diffrn_orient_matrix_UB_31      -0.0299591000
_diffrn_orient_matrix_UB_32      0.0254431000
_diffrn_orient_matrix_UB_33      0.0543713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5048
_reflns_number_total             5774
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.120
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_coef       0.0029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.018
_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)+(0.0517P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1100
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C32(H32), C33(H33), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
;
_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 0.06774(18) -0.06365(18) 0.29381(6) 0.0795(5) Uani 1 d . . .
N1 N 0.35638(15) -0.02740(15) 0.41803(5) 0.0466(3) Uani 1 d . . .
N2 N 0.55256(15) -0.03557(15) 0.45852(5) 0.0476(3) Uani 1 d . . .
C1 C 0.31233(17) 0.04136(19) 0.37873(6) 0.0459(4) Uani 1 d . . .
C2 C 0.23464(18) -0.03870(19) 0.35095(6) 0.0474(4) Uani 1 d . . .
C3 C 0.23131(19) -0.15847(19) 0.37524(7) 0.0499(4) Uani 1 d . . .
C4 C 0.30764(19) -0.14817(18) 0.41532(7) 0.0497(4) Uani 1 d . . .
H4 H 0.3245 -0.2126 0.4376 0.060 Uiso 1 calc . . R
C5 C 0.3461(2) 0.17396(19) 0.37111(6) 0.0492(4) Uani 1 d . . .
C6 C 0.4732(2) 0.2158(2) 0.37548(8) 0.0640(5) Uani 1 d . . .
H6 H 0.5372 0.1607 0.3863 0.077 Uiso 1 calc . . R
C7 C 0.5045(3) 0.3391(3) 0.36380(11) 0.0865(8) Uani 1 d . . .
H7 H 0.5893 0.3668 0.3669 0.104 Uiso 1 calc . . R
C8 C 0.4103(4) 0.4209(3) 0.34761(11) 0.0959(10) Uani 1 d . . .
H8 H 0.4319 0.5034 0.3394 0.115 Uiso 1 calc . . R
C9 C 0.2840(3) 0.3807(2) 0.34358(9) 0.0780(7) Uani 1 d . . .
H9 H 0.2206 0.4360 0.3326 0.094 Uiso 1 calc . . R
C10 C 0.2516(2) 0.2586(2) 0.35584(7) 0.0569(5) Uani 1 d . . .
H10 H 0.1659 0.2327 0.3539 0.068 Uiso 1 calc . . R
C11 C 0.1694(2) -0.0127(2) 0.30366(7) 0.0546(5) Uani 1 d . . .
C12 C 0.2321(2) 0.0726(2) 0.26729(6) 0.0520(4) Uani 1 d . . .
C13 C 0.3653(2) 0.0823(2) 0.26245(7) 0.0591(5) Uani 1 d . . .
H13 H 0.4188 0.0344 0.2825 0.071 Uiso 1 calc . . R
C14 C 0.4190(2) 0.1620(3) 0.22830(7) 0.0647(6) Uani 1 d . . .
H14 H 0.5085 0.1662 0.2256 0.078 Uiso 1 calc . . R
C15 C 0.3443(2) 0.2357(3) 0.19800(7) 0.0656(6) Uani 1 d . . .
C16 C 0.2113(2) 0.2258(3) 0.20275(8) 0.0722(7) Uani 1 d . . .
H16 H 0.1583 0.2747 0.1828 0.087 Uiso 1 calc . . R
C17 C 0.1560(2) 0.1449(3) 0.23646(8) 0.0664(6) Uani 1 d . . .
H17 H 0.0665 0.1390 0.2385 0.080 Uiso 1 calc . . R
C18 C 0.4061(3) 0.3228(4) 0.16126(10) 0.0995(10) Uani 1 d . . .
H18A H 0.4709 0.3729 0.1772 0.149 Uiso 1 calc . . GR
H18B H 0.3415 0.3771 0.1474 0.149 Uiso 1 calc . . GR
H18C H 0.4454 0.2739 0.1357 0.149 Uiso 1 calc . . GR
C19 C 0.1636(3) -0.2766(2) 0.35883(8) 0.0674(6) Uani 1 d . . .
H19A H 0.0726 -0.2605 0.3560 0.101 Uiso 1 calc . . GR
H19B H 0.1779 -0.3423 0.3824 0.101 Uiso 1 calc . . GR
H19C H 0.1970 -0.3023 0.3276 0.101 Uiso 1 calc . . GR
C20 C 0.62839(17) -0.01261(18) 0.49772(7) 0.0474(4) Uani 1 d . . .
C21 C 0.58275(19) 0.05554(19) 0.53727(7) 0.0498(4) Uani 1 d . . .
H21 H 0.6354 0.0672 0.5645 0.060 Uiso 1 calc . . R
C22 C 0.45954(19) 0.10671(18) 0.53689(7) 0.0481(4) Uani 1 d . . .
C23 C 0.38043(18) 0.08673(18) 0.49570(6) 0.0471(4) Uani 1 d . . .
C24 C 0.43460(18) 0.01245(18) 0.45881(6) 0.0460(4) Uani 1 d . . .
C25 C 0.76100(18) -0.06626(19) 0.49596(7) 0.0522(4) Uani 1 d . . .
C26 C 0.7920(2) -0.1579(3) 0.46162(8) 0.0677(6) Uani 1 d . . .
H26 H 0.7290 -0.1860 0.4399 0.081 Uiso 1 calc . . R
C27 C 0.9150(3) -0.2078(3) 0.45924(10) 0.0851(8) Uani 1 d . . .
H27 H 0.9342 -0.2701 0.4364 0.102 Uiso 1 calc . . R
C28 C 1.0094(2) -0.1654(3) 0.49075(11) 0.0858(9) Uani 1 d . . .
H28 H 1.0930 -0.1971 0.4886 0.103 Uiso 1 calc . . R
C29 C 0.9797(2) -0.0763(3) 0.52538(11) 0.0772(7) Uani 1 d . . .
H29 H 1.0427 -0.0494 0.5473 0.093 Uiso 1 calc . . R
C30 C 0.8566(2) -0.0262(2) 0.52779(9) 0.0621(5) Uani 1 d . . .
H30 H 0.8377 0.0351 0.5511 0.075 Uiso 1 calc . . R
C31 C 0.41442(19) 0.1761(2) 0.58132(6) 0.0506(4) Uani 1 d . . .
C32 C 0.4073(3) 0.1149(2) 0.62573(8) 0.0662(6) Uani 1 d . . .
H32 H 0.4289 0.0299 0.6277 0.079 Uiso 1 calc . . R
C33 C 0.3681(3) 0.1787(3) 0.66776(8) 0.0746(7) Uani 1 d . . .
H33 H 0.3629 0.1353 0.6973 0.090 Uiso 1 calc . . R
C34 C 0.3370(2) 0.3042(3) 0.66639(8) 0.0654(6) Uani 1 d . . .
C35 C 0.3482(3) 0.3659(2) 0.62251(9) 0.0768(7) Uani 1 d . . .
H35 H 0.3303 0.4518 0.6210 0.092 Uiso 1 calc . . R
C36 C 0.3855(3) 0.3030(2) 0.58033(8) 0.0695(6) Uani 1 d . . .
H36 H 0.3912 0.3470 0.5509 0.083 Uiso 1 calc . . R
C37 C 0.2909(3) 0.3719(3) 0.71210(10) 0.0925(9) Uani 1 d . . .
H37A H 0.2883 0.3136 0.7390 0.139 Uiso 1 calc . . GR
H37B H 0.2059 0.4054 0.7065 0.139 Uiso 1 calc . . GR
H37C H 0.3491 0.4396 0.7197 0.139 Uiso 1 calc . . GR
C38 C 0.2451(2) 0.1367(2) 0.49207(8) 0.0606(5) Uani 1 d . . .
H38A H 0.2099 0.1470 0.5244 0.091 Uiso 1 calc . . GR
H38B H 0.1928 0.0784 0.4739 0.091 Uiso 1 calc . . GR
H38C H 0.2461 0.2168 0.4756 0.091 Uiso 1 calc . . GR


_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 C11 1.213(3) . ?
N1 C1 1.375(2) . ?
N1 C4 1.378(3) . ?
N1 C24 1.439(2) . ?
N2 C20 1.349(2) . ?
N2 C24 1.323(2) . ?
C1 C2 1.393(3) . ?
C1 C5 1.463(3) . ?
C2 C3 1.433(3) . ?
C2 C11 1.482(3) . ?
C3 C4 1.354(3) . ?
C3 C19 1.503(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 C10 1.391(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.490(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(3) . ?
C15 C16 1.386(3) . ?
C15 C18 1.506(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.382(3) . ?
C20 C25 1.486(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 C23 1.407(3) . ?
C22 C31 1.493(3) . ?
C23 C24 1.396(3) . ?
C23 C38 1.500(3) . ?
C25 C26 1.387(3) . ?
C25 C30 1.383(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.371(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.376(3) . ?
C31 C36 1.379(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.392(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.370(4) . ?
C34 C35 1.369(3) . ?
C34 C37 1.516(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.385(3) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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
C1 N1 C4 109.23(16) . . ?
C1 N1 C24 129.36(16) . . ?
C4 N1 C24 121.33(15) . . ?
C24 N2 C20 117.57(16) . . ?
N1 C1 C2 107.04(17) . . ?
N1 C1 C5 122.76(16) . . ?
C2 C1 C5 130.20(17) . . ?
C1 C2 C3 107.57(16) . . ?
C1 C2 C11 128.54(18) . . ?
C3 C2 C11 123.84(17) . . ?
C2 C3 C19 127.69(17) . . ?
C4 C3 C2 106.76(17) . . ?
C4 C3 C19 125.46(19) . . ?
N1 C4 H4 125.3 . . ?
C3 C4 N1 109.38(17) . . ?
C3 C4 H4 125.3 . . ?
C6 C5 C1 121.24(19) . . ?
C10 C5 C1 119.66(18) . . ?
C10 C5 C6 118.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
O1 C11 C2 120.33(19) . . ?
O1 C11 C12 119.98(18) . . ?
C2 C11 C12 119.64(18) . . ?
C13 C12 C11 122.69(19) . . ?
C17 C12 C11 119.6(2) . . ?
C17 C12 C13 117.7(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.9(2) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 117.3(2) . . ?
C14 C15 C18 120.6(2) . . ?
C16 C15 C18 122.0(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 120.99(17) . . ?
N2 C20 C25 116.27(17) . . ?
C21 C20 C25 122.74(17) . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.88(17) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 118.86(18) . . ?
C21 C22 C31 118.32(17) . . ?
C23 C22 C31 122.76(17) . . ?
C22 C23 C38 122.87(18) . . ?
C24 C23 C22 115.32(17) . . ?
C24 C23 C38 121.77(17) . . ?
N2 C24 N1 113.67(16) . . ?
N2 C24 C23 126.31(16) . . ?
C23 C24 N1 119.83(16) . . ?
C26 C25 C20 120.20(19) . . ?
C30 C25 C20 121.5(2) . . ?
C30 C25 C26 118.3(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0(3) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.8(2) . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C22 119.99(19) . . ?
C32 C31 C36 117.7(2) . . ?
C36 C31 C22 122.18(18) . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.8(2) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.2(2) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C37 120.8(2) . . ?
C35 C34 C33 117.9(2) . . ?
C35 C34 C37 121.4(3) . . ?
C34 C35 H35 119.3 . . ?
C34 C35 C36 121.4(2) . . ?
C36 C35 H35 119.3 . . ?
C31 C36 C35 120.9(2) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C23 C38 H38A 109.5 . . ?
C23 C38 H38B 109.5 . . ?
C23 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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 C11 C12 C13 -145.8(2) . . . . ?
O1 C11 C12 C17 33.6(3) . . . . ?
N1 C1 C2 C3 0.9(2) . . . . ?
N1 C1 C2 C11 -176.63(18) . . . . ?
N1 C1 C5 C6 46.8(3) . . . . ?
N1 C1 C5 C10 -137.78(18) . . . . ?
N2 C20 C21 C22 -2.7(3) . . . . ?
N2 C20 C25 C26 -14.5(3) . . . . ?
N2 C20 C25 C30 164.93(18) . . . . ?
C1 N1 C4 C3 -0.8(2) . . . . ?
C1 N1 C24 N2 -110.8(2) . . . . ?
C1 N1 C24 C23 74.0(2) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C19 -178.1(2) . . . . ?
C1 C2 C11 O1 -148.9(2) . . . . ?
C1 C2 C11 C12 33.7(3) . . . . ?
C1 C5 C6 C7 174.2(2) . . . . ?
C1 C5 C10 C9 -173.23(19) . . . . ?
C2 C1 C5 C6 -133.6(2) . . . . ?
C2 C1 C5 C10 41.8(3) . . . . ?
C2 C3 C4 N1 1.3(2) . . . . ?
C2 C11 C12 C13 31.6(3) . . . . ?
C2 C11 C12 C17 -148.9(2) . . . . ?
C3 C2 C11 O1 34.0(3) . . . . ?
C3 C2 C11 C12 -143.5(2) . . . . ?
C4 N1 C1 C2 -0.1(2) . . . . ?
C4 N1 C1 C5 179.56(17) . . . . ?
C4 N1 C24 N2 73.0(2) . . . . ?
C4 N1 C24 C23 -102.2(2) . . . . ?
C5 C1 C2 C3 -178.73(18) . . . . ?
C5 C1 C2 C11 3.7(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C5 C10 C9 2.3(3) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C5 -1.7(4) . . . . ?
C10 C5 C6 C7 -1.3(3) . . . . ?
C11 C2 C3 C4 176.30(18) . . . . ?
C11 C2 C3 C19 -0.4(3) . . . . ?
C11 C12 C13 C14 179.9(2) . . . . ?
C11 C12 C17 C16 179.3(2) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C12 C17 C16 -1.3(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C13 C14 C15 C18 179.5(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C12 1.2(4) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C18 C15 C16 C17 179.6(3) . . . . ?
C19 C3 C4 N1 178.14(19) . . . . ?
C20 N2 C24 N1 -173.99(16) . . . . ?
C20 N2 C24 C23 0.9(3) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C20 C21 C22 C31 178.21(18) . . . . ?
C20 C25 C26 C27 179.4(2) . . . . ?
C20 C25 C30 C29 -179.4(2) . . . . ?
C21 C20 C25 C26 164.5(2) . . . . ?
C21 C20 C25 C30 -16.1(3) . . . . ?
C21 C22 C23 C24 1.6(3) . . . . ?
C21 C22 C23 C38 179.18(19) . . . . ?
C21 C22 C31 C32 -60.2(3) . . . . ?
C21 C22 C31 C36 116.2(2) . . . . ?
C22 C23 C24 N1 171.99(17) . . . . ?
C22 C23 C24 N2 -2.6(3) . . . . ?
C22 C31 C32 C33 178.6(2) . . . . ?
C22 C31 C36 C35 -177.7(2) . . . . ?
C23 C22 C31 C32 117.0(2) . . . . ?
C23 C22 C31 C36 -66.5(3) . . . . ?
C24 N1 C1 C2 -176.72(17) . . . . ?
C24 N1 C1 C5 3.0(3) . . . . ?
C24 N1 C4 C3 176.15(16) . . . . ?
C24 N2 C20 C21 1.8(3) . . . . ?
C24 N2 C20 C25 -179.13(16) . . . . ?
C25 C20 C21 C22 178.32(18) . . . . ?
C25 C26 C27 C28 -1.0(4) . . . . ?
C26 C25 C30 C29 0.0(3) . . . . ?
C26 C27 C28 C29 1.9(4) . . . . ?
C27 C28 C29 C30 -2.0(4) . . . . ?
C28 C29 C30 C25 1.0(4) . . . . ?
C30 C25 C26 C27 0.0(3) . . . . ?
C31 C22 C23 C24 -175.63(18) . . . . ?
C31 C22 C23 C38 2.0(3) . . . . ?
C31 C32 C33 C34 -0.8(4) . . . . ?
C32 C31 C36 C35 -1.2(4) . . . . ?
C32 C33 C34 C35 -1.3(4) . . . . ?
C32 C33 C34 C37 178.3(3) . . . . ?
C33 C34 C35 C36 2.1(4) . . . . ?
C34 C35 C36 C31 -0.9(5) . . . . ?
C36 C31 C32 C33 2.0(4) . . . . ?
C37 C34 C35 C36 -177.5(3) . . . . ?
C38 C23 C24 N1 -5.6(3) . . . . ?
C38 C23 C24 N2 179.78(19) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
