# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_exp_3313
_database_code_depnum_ccdc_archive 'CCDC 1544597'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_audit_creation_date             2015-06-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C16 H10 N2)'
_chemical_formula_sum            'C32 H20 N4'
_chemical_formula_weight         460.52
_chemical_melting_point          ?
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'

_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                   6.6509(6)
_cell_length_b                   7.9140(6)
_cell_length_c                   12.3019(11)
_cell_angle_alpha                90.852(6)
_cell_angle_beta                 104.072(7)
_cell_angle_gamma                112.181(7)
_cell_volume                     577.48(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1368
_cell_measurement_temperature    102.3
_cell_measurement_theta_max      29.3193
_cell_measurement_theta_min      3.1002
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4122
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_temperature      102.3
_diffrn_detector_area_resol_mean 16.0971
_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  -46.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   51.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega    8.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0655779000
_diffrn_orient_matrix_UB_12      -0.0907231000
_diffrn_orient_matrix_UB_13      -0.0271960000
_diffrn_orient_matrix_UB_21      0.0512997000
_diffrn_orient_matrix_UB_22      0.0212323000
_diffrn_orient_matrix_UB_23      -0.0450435000
_diffrn_orient_matrix_UB_31      0.0858148000
_diffrn_orient_matrix_UB_32      -0.0286460000
_diffrn_orient_matrix_UB_33      0.0285536000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1848
_reflns_number_total             2262
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0419
_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)+(0.0322P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0951
_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. 
;
_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
N1 N 0.50587(19) 0.65005(15) 0.10600(10) 0.0173(3) Uani 1 1 d . . .
C5 C 0.2127(2) 0.76631(19) 0.08112(13) 0.0191(3) Uani 1 1 d . . .
H5 H 0.1127 0.6573 0.0324 0.023 Uiso 1 1 calc R . .
C10 C 0.2042(2) 1.20262(19) 0.19074(13) 0.0201(3) Uani 1 1 d . . .
C6 C 0.1375(2) 0.90053(19) 0.10165(13) 0.0193(3) Uani 1 1 d . . .
H6 H -0.0142 0.8837 0.0675 0.023 Uiso 1 1 calc R . .
C8 C 0.5057(2) 1.08411(19) 0.22354(13) 0.0201(3) Uani 1 1 d . . .
H8 H 0.6051 1.1926 0.2728 0.024 Uiso 1 1 calc R . .
N2 N 0.1359(2) 1.31310(17) 0.20277(12) 0.0263(3) Uani 1 1 d . . .
C7 C 0.2841(2) 1.06124(18) 0.17266(12) 0.0184(3) Uani 1 1 d . . .
C9 C 0.5813(2) 0.95011(19) 0.20273(13) 0.0197(3) Uani 1 1 d . . .
H9 H 0.7329 0.9668 0.2369 0.024 Uiso 1 1 calc R . .
C4 C 0.4341(2) 0.78934(18) 0.13121(12) 0.0169(3) Uani 1 1 d . . .
C16 C 0.6351(3) 0.65827(19) 0.36818(13) 0.0219(3) Uani 1 1 d . . .
H16 H 0.4786 0.6291 0.3379 0.026 Uiso 1 1 calc R . .
C2 C 0.6698(2) 0.59647(18) 0.17411(13) 0.0180(3) Uani 1 1 d . . .
C1 C 0.4384(2) 0.55330(18) -0.00094(12) 0.0169(3) Uani 1 1 d . . .
C11 C 0.7665(2) 0.65309(18) 0.29615(13) 0.0185(3) Uani 1 1 d . . .
C3 C 0.7055(2) 0.47115(18) 0.11065(12) 0.0176(3) Uani 1 1 d . . .
H3 H 0.8069 0.4127 0.1356 0.021 Uiso 1 1 calc R . .
C12 C 0.9953(3) 0.6934(2) 0.34345(14) 0.0253(4) Uani 1 1 d . . .
H12 H 1.0872 0.6891 0.2961 0.030 Uiso 1 1 calc R . .
C15 C 0.7310(3) 0.7056(2) 0.48343(14) 0.0254(4) Uani 1 1 d . . .
H15 H 0.6403 0.7098 0.5315 0.030 Uiso 1 1 calc R . .
C13 C 1.0892(3) 0.7398(2) 0.45902(14) 0.0320(4) Uani 1 1 d . . .
H13 H 1.2450 0.7670 0.4902 0.038 Uiso 1 1 calc R . .
C14 C 0.9580(3) 0.7467(2) 0.52884(14) 0.0296(4) Uani 1 1 d . . .
H14 H 1.0233 0.7797 0.6078 0.036 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
N1 C4 1.4136(17) . ?
N1 C2 1.4091(18) . ?
N1 C1 1.3936(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3774(19) . ?
C5 C4 1.3906(19) . ?
C10 N2 1.1494(18) . ?
C10 C7 1.4432(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.394(2) . ?
C8 C9 1.3783(19) . ?
C9 H9 0.9500 . ?
C9 C4 1.400(2) . ?
C16 H16 0.9500 . ?
C16 C11 1.398(2) . ?
C16 C15 1.386(2) . ?
C2 C11 1.470(2) . ?
C2 C3 1.377(2) . ?
C1 C1 1.377(3) 2_665 ?
C1 C3 1.414(2) 2_665 ?
C11 C12 1.397(2) . ?
C3 C1 1.414(2) 2_665 ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 129.05(12) . . ?
C1 N1 C4 123.34(12) . . ?
C1 N1 C2 107.25(11) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.40(13) . . ?
C4 C5 H5 119.8 . . ?
N2 C10 C7 178.25(16) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.98(13) . . ?
C7 C6 H6 120.0 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.33(13) . . ?
C6 C7 C10 119.23(13) . . ?
C8 C7 C10 121.05(13) . . ?
C8 C7 C6 119.71(13) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C4 119.84(14) . . ?
C4 C9 H9 120.1 . . ?
C5 C4 N1 118.61(13) . . ?
C5 C4 C9 119.73(13) . . ?
C9 C4 N1 121.64(13) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C11 120.58(14) . . ?
N1 C2 C11 124.15(12) . . ?
C3 C2 N1 109.19(13) . . ?
C3 C2 C11 126.37(13) . . ?
N1 C1 C3 142.88(13) . 2_665 ?
C1 C1 N1 107.91(16) 2_665 . ?
C1 C1 C3 109.19(16) 2_665 2_665 ?
C16 C11 C2 122.29(13) . . ?
C12 C11 C16 118.37(14) . . ?
C12 C11 C2 119.24(13) . . ?
C2 C3 C1 106.45(12) . 2_665 ?
C2 C3 H3 126.8 . . ?
C1 C3 H3 126.8 2_665 . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.53(15) . . ?
C13 C12 H12 119.7 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.36(15) . . ?
C14 C15 H15 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.42(15) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.74(16) . . ?
C13 C14 H14 120.1 . . ?

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
N1 C2 C11 C16 41.8(2) . . . . ?
N1 C2 C11 C12 -141.87(14) . . . . ?
N1 C2 C3 C1 0.15(16) . . . 2_665 ?
C5 C6 C7 C10 178.29(13) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C5 C4 N1 -178.66(13) . . . . ?
C6 C5 C4 C9 -0.1(2) . . . . ?
C8 C9 C4 N1 178.82(13) . . . . ?
C8 C9 C4 C5 0.3(2) . . . . ?
N2 C10 C7 C6 -15(5) . . . . ?
N2 C10 C7 C8 164(5) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
C9 C8 C7 C10 -178.05(13) . . . . ?
C9 C8 C7 C6 0.9(2) . . . . ?
C4 N1 C2 C11 13.4(2) . . . . ?
C4 N1 C2 C3 -172.38(12) . . . . ?
C4 N1 C1 C1 172.24(14) . . . 2_665 ?
C4 N1 C1 C3 -5.4(3) . . . 2_665 ?
C4 C5 C6 C7 0.3(2) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C16 C15 C14 C13 -0.3(2) . . . . ?
C2 N1 C4 C5 -149.57(14) . . . . ?
C2 N1 C4 C9 31.9(2) . . . . ?
C2 N1 C1 C1 -1.38(18) . . . 2_665 ?
C2 N1 C1 C3 -179.03(18) . . . 2_665 ?
C2 C11 C12 C13 -177.31(13) . . . . ?
C1 N1 C4 C5 38.28(18) . . . . ?
C1 N1 C4 C9 -140.23(14) . . . . ?
C1 N1 C2 C11 -173.43(12) . . . . ?
C1 N1 C2 C3 0.76(15) . . . . ?
C11 C16 C15 C14 -0.6(2) . . . . ?
C11 C2 C3 C1 174.18(13) . . . 2_665 ?
C11 C12 C13 C14 0.0(2) . . . . ?
C3 C2 C11 C16 -131.36(16) . . . . ?
C3 C2 C11 C12 45.0(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C15 C16 C11 C2 177.50(13) . . . . ?
C15 C16 C11 C12 1.2(2) . . . . ?

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1544601'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H30 N2 O8'
_chemical_formula_weight         642.64

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.1457(11)
_cell_length_b                   11.6511(12)
_cell_length_c                   13.2828(14)
_cell_angle_alpha                82.622(3)
_cell_angle_beta                 83.818(3)
_cell_angle_gamma                80.790(3)
_cell_volume                     1681.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1178
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.70

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11030
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.17
_reflns_number_total             6005
_reflns_number_gt                3104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1198P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6005
_refine_ls_number_parameters     437
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2422
_refine_ls_wR_factor_gt          0.1979
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1206(5) 0.4047(5) 0.3327(5) 0.123(2) Uani 1 1 d . . .
H1A H 1.0940 0.3387 0.3750 0.185 Uiso 1 1 calc R . .
H1B H 1.1994 0.4150 0.3498 0.185 Uiso 1 1 calc R . .
H1C H 1.1258 0.3912 0.2624 0.185 Uiso 1 1 calc R . .
C2 C 0.9168(4) 0.5084(4) 0.3403(3) 0.0680(12) Uani 1 1 d . . .
C3 C 0.8409(4) 0.6176(3) 0.3605(3) 0.0588(11) Uani 1 1 d . . .
C4 C 0.8879(4) 0.7164(4) 0.3775(3) 0.0630(11) Uani 1 1 d . . .
H4 H 0.9719 0.7129 0.3770 0.076 Uiso 1 1 calc R . .
C5 C 0.8136(3) 0.8181(4) 0.3949(3) 0.0592(11) Uani 1 1 d . . .
H5 H 0.8476 0.8830 0.4054 0.071 Uiso 1 1 calc R . .
C6 C 0.6873(3) 0.8257(3) 0.3970(3) 0.0529(10) Uani 1 1 d . . .
C7 C 0.6391(4) 0.7285(4) 0.3814(3) 0.0730(13) Uani 1 1 d U . .
H7 H 0.5549 0.7325 0.3832 0.088 Uiso 1 1 calc R . .
C8 C 0.7125(4) 0.6266(4) 0.3632(3) 0.0665(11) Uani 1 1 d U . .
H8 H 0.6778 0.5622 0.3525 0.080 Uiso 1 1 calc R . .
C9 C 0.5185(3) 0.9419(3) 0.4975(3) 0.0522(9) Uani 1 1 d U . .
C10 C 0.6198(3) 1.0463(3) 0.3713(3) 0.0540(10) Uani 1 1 d . . .
C11 C 0.5400(3) 1.1255(3) 0.4256(3) 0.0561(10) Uani 1 1 d . . .
H11 H 0.5285 1.2067 0.4128 0.067 Uiso 1 1 calc R . .
C12 C 0.6946(3) 1.0748(4) 0.2772(3) 0.0565(10) Uani 1 1 d . . .
C13 C 0.7183(4) 0.9995(4) 0.1988(3) 0.0641(11) Uani 1 1 d . . .
H13 H 0.6915 0.9270 0.2087 0.077 Uiso 1 1 calc R . .
C14 C 0.7811(4) 1.0349(4) 0.1082(3) 0.0683(12) Uani 1 1 d . . .
H14 H 0.7954 0.9857 0.0569 0.082 Uiso 1 1 calc R . .
C15 C 0.8240(4) 1.1422(4) 0.0910(3) 0.0633(11) Uani 1 1 d . . .
C16 C 0.8024(4) 1.2136(4) 0.1674(3) 0.0669(12) Uani 1 1 d . . .
H16 H 0.8308 1.2854 0.1575 0.080 Uiso 1 1 calc R . .
C17 C 0.7404(3) 1.1809(3) 0.2573(3) 0.0550(10) Uani 1 1 d . . .
H17 H 0.7278 1.2311 0.3077 0.066 Uiso 1 1 calc R . .
C18 C 0.8896(4) 1.1747(5) -0.0077(4) 0.0819(15) Uani 1 1 d . . .
C19 C 1.0030(6) 1.3134(6) -0.1070(4) 0.141(3) Uani 1 1 d . . .
H19A H 1.0677 1.2523 -0.1243 0.211 Uiso 1 1 calc R . .
H19B H 1.0368 1.3825 -0.1000 0.211 Uiso 1 1 calc R . .
H19C H 0.9485 1.3304 -0.1600 0.211 Uiso 1 1 calc R . .
C20 C 0.5348(5) 1.1856(5) -0.0654(4) 0.111(2) Uani 1 1 d . . .
H20A H 0.4862 1.1850 -0.1207 0.166 Uiso 1 1 calc R . .
H20B H 0.6108 1.1349 -0.0758 0.166 Uiso 1 1 calc R . .
H20C H 0.5502 1.2638 -0.0627 0.166 Uiso 1 1 calc R . .
C21 C 0.3504(4) 1.1782(4) 0.0380(4) 0.0747(13) Uani 1 1 d . . .
C22 C 0.2904(3) 1.1310(3) 0.1358(3) 0.0539(10) Uani 1 1 d . . .
C23 C 0.1640(4) 1.1450(4) 0.1459(3) 0.0675(12) Uani 1 1 d . . .
H23 H 0.1197 1.1883 0.0947 0.081 Uiso 1 1 calc R . .
C24 C 0.1038(3) 1.0938(3) 0.2332(3) 0.0592(11) Uani 1 1 d . . .
H24 H 0.0190 1.1025 0.2400 0.071 Uiso 1 1 calc R . .
C25 C 0.1683(3) 1.0306(3) 0.3093(3) 0.0420(8) Uani 1 1 d . . .
C26 C 0.2940(3) 1.0207(3) 0.3010(3) 0.0552(10) Uani 1 1 d . . .
H26 H 0.3379 0.9808 0.3538 0.066 Uiso 1 1 calc R . .
C27 C 0.3541(3) 1.0703(3) 0.2141(3) 0.0600(11) Uani 1 1 d . . .
H27 H 0.4388 1.0625 0.2083 0.072 Uiso 1 1 calc R . .
C28 C 0.0113(3) 1.0366(3) 0.4563(2) 0.0425(8) Uani 1 1 d . . .
C29 C -0.0649(3) 1.1448(3) 0.4599(3) 0.0449(9) Uani 1 1 d . . .
H29 H -0.0670 1.2094 0.4108 0.054 Uiso 1 1 calc R . .
C30 C 0.1362(3) 0.8648(3) 0.4481(3) 0.0423(8) Uani 1 1 d . . .
C31 C 0.2175(3) 0.7719(3) 0.4011(3) 0.0418(8) Uani 1 1 d . . .
C32 C 0.2241(3) 0.7632(3) 0.2972(3) 0.0470(9) Uani 1 1 d . . .
H32 H 0.1782 0.8198 0.2553 0.056 Uiso 1 1 calc R . .
C33 C 0.2982(3) 0.6712(3) 0.2555(3) 0.0505(9) Uani 1 1 d . . .
H33 H 0.3020 0.6670 0.1858 0.061 Uiso 1 1 calc R . .
C34 C 0.3671(3) 0.5848(3) 0.3162(3) 0.0460(9) Uani 1 1 d . . .
C35 C 0.3585(3) 0.5911(3) 0.4197(3) 0.0515(9) Uani 1 1 d . . .
H35 H 0.4027 0.5331 0.4615 0.062 Uiso 1 1 calc R . .
C36 C 0.2848(3) 0.6828(3) 0.4618(3) 0.0504(9) Uani 1 1 d . . .
H36 H 0.2798 0.6855 0.5318 0.061 Uiso 1 1 calc R . .
C37 C 0.4500(4) 0.4871(4) 0.2745(3) 0.0592(10) Uani 1 1 d . . .
C38 C 0.5250(8) 0.3957(6) 0.1262(5) 0.184(4) Uani 1 1 d . . .
H38A H 0.6080 0.4081 0.1271 0.276 Uiso 1 1 calc R . .
H38B H 0.5067 0.3972 0.0571 0.276 Uiso 1 1 calc R . .
H38C H 0.5141 0.3212 0.1632 0.276 Uiso 1 1 calc R . .
N1 N 0.6088(3) 0.9349(3) 0.4133(2) 0.0532(8) Uani 1 1 d U . .
N2 N 0.1043(2) 0.9764(2) 0.3959(2) 0.0425(7) Uani 1 1 d . . .
O1 O 0.8813(3) 0.4227(3) 0.3188(3) 0.0977(11) Uani 1 1 d . . .
O2 O 1.0352(3) 0.5076(3) 0.3487(3) 0.0971(12) Uani 1 1 d . . .
O3 O 0.9009(4) 1.1203(4) -0.0790(3) 0.1270(15) Uani 1 1 d . . .
O4 O 0.9365(3) 1.2757(4) -0.0114(3) 0.1107(13) Uani 1 1 d . . .
O5 O 0.4698(3) 1.1447(3) 0.0299(2) 0.0898(11) Uani 1 1 d . . .
O6 O 0.2994(3) 1.2360(4) -0.0295(3) 0.1244(16) Uani 1 1 d . . .
O7 O 0.5165(3) 0.4149(3) 0.3230(2) 0.0799(9) Uani 1 1 d . . .
O8 O 0.4428(4) 0.4887(3) 0.1743(3) 0.1113(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.430(6) . ?
C2 O1 1.207(5) . ?
C2 O2 1.336(5) . ?
C2 C3 1.449(6) . ?
C3 C4 1.391(5) . ?
C3 C8 1.415(5) . ?
C4 C5 1.363(5) . ?
C5 C6 1.394(5) . ?
C6 C7 1.376(5) . ?
C6 N1 1.450(5) . ?
C7 C8 1.363(6) . ?
C9 C9 1.358(7) 2_676 ?
C9 C11 1.378(5) 2_676 ?
C9 N1 1.423(4) . ?
C10 N1 1.365(4) . ?
C10 C11 1.391(5) . ?
C10 C12 1.457(5) . ?
C11 C9 1.378(5) 2_676 ?
C12 C17 1.396(5) . ?
C12 C13 1.423(5) . ?
C13 C14 1.376(5) . ?
C14 C15 1.391(6) . ?
C15 C16 1.372(6) . ?
C15 C18 1.467(6) . ?
C16 C17 1.356(5) . ?
C18 O3 1.191(6) . ?
C18 O4 1.357(6) . ?
C19 O4 1.454(5) . ?
C20 O5 1.453(5) . ?
C21 O6 1.188(5) . ?
C21 O5 1.322(5) . ?
C21 C22 1.478(5) . ?
C22 C27 1.376(5) . ?
C22 C23 1.387(5) . ?
C23 C24 1.390(5) . ?
C24 C25 1.369(5) . ?
C25 C26 1.381(5) . ?
C25 N2 1.418(4) . ?
C26 C27 1.379(5) . ?
C28 C28 1.376(6) 2_576 ?
C28 N2 1.394(4) . ?
C28 C29 1.406(5) . ?
C29 C30 1.386(4) 2_576 ?
C30 C29 1.386(4) 2_576 ?
C30 N2 1.405(4) . ?
C30 C31 1.456(5) . ?
C31 C32 1.390(5) . ?
C31 C36 1.398(5) . ?
C32 C33 1.382(5) . ?
C33 C34 1.389(5) . ?
C34 C35 1.378(5) . ?
C34 C37 1.474(5) . ?
C35 C36 1.379(5) . ?
C37 O7 1.198(5) . ?
C37 O8 1.339(5) . ?
C38 O8 1.468(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
O1 C2 O2 120.3(4) . . ?
O1 C2 C3 125.9(4) . . ?
O2 C2 C3 113.8(4) . . ?
C4 C3 C8 117.2(4) . . ?
C4 C3 C2 123.2(4) . . ?
C8 C3 C2 119.6(4) . . ?
C5 C4 C3 121.5(4) . . ?
C4 C5 C6 120.6(3) . . ?
C7 C6 C5 118.7(4) . . ?
C7 C6 N1 120.9(3) . . ?
C5 C6 N1 120.4(3) . . ?
C8 C7 C6 121.3(4) . . ?
C7 C8 C3 120.7(4) . . ?
C9 C9 C11 111.8(4) 2_676 2_676 ?
C9 C9 N1 105.4(4) 2_676 . ?
C11 C9 N1 142.7(3) 2_676 . ?
N1 C10 C11 109.5(3) . . ?
N1 C10 C12 124.0(3) . . ?
C11 C10 C12 126.1(4) . . ?
C9 C11 C10 105.4(3) 2_676 . ?
C17 C12 C13 116.8(3) . . ?
C17 C12 C10 121.2(3) . . ?
C13 C12 C10 121.9(4) . . ?
C14 C13 C12 119.5(4) . . ?
C13 C14 C15 121.9(4) . . ?
C16 C15 C14 118.3(4) . . ?
C16 C15 C18 122.6(4) . . ?
C14 C15 C18 119.0(4) . . ?
C17 C16 C15 120.9(4) . . ?
C16 C17 C12 122.6(4) . . ?
O3 C18 O4 122.0(5) . . ?
O3 C18 C15 124.7(6) . . ?
O4 C18 C15 113.2(5) . . ?
O6 C21 O5 121.9(4) . . ?
O6 C21 C22 125.4(4) . . ?
O5 C21 C22 112.7(4) . . ?
C27 C22 C23 119.4(3) . . ?
C27 C22 C21 123.1(4) . . ?
C23 C22 C21 117.4(4) . . ?
C22 C23 C24 119.5(4) . . ?
C25 C24 C23 120.6(3) . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 N2 119.2(3) . . ?
C26 C25 N2 120.9(3) . . ?
C27 C26 C25 119.7(4) . . ?
C22 C27 C26 120.9(3) . . ?
C28 C28 N2 107.4(4) 2_576 . ?
C28 C28 C29 110.1(4) 2_576 . ?
N2 C28 C29 142.5(3) . . ?
C30 C29 C28 105.8(3) 2_576 . ?
C29 C30 N2 109.3(3) 2_576 . ?
C29 C30 C31 127.5(3) 2_576 . ?
N2 C30 C31 122.5(3) . . ?
C32 C31 C36 117.9(3) . . ?
C32 C31 C30 121.9(3) . . ?
C36 C31 C30 120.0(3) . . ?
C33 C32 C31 120.6(3) . . ?
C32 C33 C34 121.0(3) . . ?
C35 C34 C33 118.7(3) . . ?
C35 C34 C37 118.5(4) . . ?
C33 C34 C37 122.8(4) . . ?
C34 C35 C36 120.6(4) . . ?
C35 C36 C31 121.2(3) . . ?
O7 C37 O8 123.5(4) . . ?
O7 C37 C34 125.0(4) . . ?
O8 C37 C34 111.5(4) . . ?
C10 N1 C9 107.8(3) . . ?
C10 N1 C6 129.7(3) . . ?
C9 N1 C6 121.1(3) . . ?
C28 N2 C30 107.4(3) . . ?
C28 N2 C25 123.5(3) . . ?
C30 N2 C25 127.8(3) . . ?
C2 O2 C1 119.9(4) . . ?
C18 O4 C19 116.3(4) . . ?
C21 O5 C20 115.8(4) . . ?
C37 O8 C38 115.0(4) . . ?

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 C2 C3 C4 -175.1(4) . . . . ?
O2 C2 C3 C4 5.9(6) . . . . ?
O1 C2 C3 C8 4.7(7) . . . . ?
O2 C2 C3 C8 -174.3(4) . . . . ?
C8 C3 C4 C5 -0.8(6) . . . . ?
C2 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C4 C5 C6 N1 -178.7(4) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
N1 C6 C7 C8 178.2(4) . . . . ?
C6 C7 C8 C3 0.4(7) . . . . ?
C4 C3 C8 C7 0.3(6) . . . . ?
C2 C3 C8 C7 -179.5(4) . . . . ?
N1 C10 C11 C9 0.7(4) . . . 2_676 ?
C12 C10 C11 C9 174.3(4) . . . 2_676 ?
N1 C10 C12 C17 -155.3(4) . . . . ?
C11 C10 C12 C17 32.0(6) . . . . ?
N1 C10 C12 C13 28.5(6) . . . . ?
C11 C10 C12 C13 -144.2(4) . . . . ?
C17 C12 C13 C14 -1.6(6) . . . . ?
C10 C12 C13 C14 174.8(4) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C13 C14 C15 C18 -179.6(4) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C18 C15 C16 C17 179.4(4) . . . . ?
C15 C16 C17 C12 -0.4(6) . . . . ?
C13 C12 C17 C16 1.4(6) . . . . ?
C10 C12 C17 C16 -175.0(4) . . . . ?
C16 C15 C18 O3 -173.1(5) . . . . ?
C14 C15 C18 O3 6.7(7) . . . . ?
C16 C15 C18 O4 6.2(6) . . . . ?
C14 C15 C18 O4 -174.1(4) . . . . ?
O6 C21 C22 C27 -176.0(5) . . . . ?
O5 C21 C22 C27 7.0(6) . . . . ?
O6 C21 C22 C23 7.0(7) . . . . ?
O5 C21 C22 C23 -170.0(4) . . . . ?
C27 C22 C23 C24 -2.4(6) . . . . ?
C21 C22 C23 C24 174.7(4) . . . . ?
C22 C23 C24 C25 0.5(6) . . . . ?
C23 C24 C25 C26 2.1(6) . . . . ?
C23 C24 C25 N2 -178.0(3) . . . . ?
C24 C25 C26 C27 -2.8(6) . . . . ?
N2 C25 C26 C27 177.3(3) . . . . ?
C23 C22 C27 C26 1.7(6) . . . . ?
C21 C22 C27 C26 -175.2(4) . . . . ?
C25 C26 C27 C22 0.9(6) . . . . ?
C28 C28 C29 C30 -0.8(5) 2_576 . . 2_576 ?
N2 C28 C29 C30 -179.2(4) . . . 2_576 ?
C29 C30 C31 C32 138.4(4) 2_576 . . . ?
N2 C30 C31 C32 -30.8(5) . . . . ?
C29 C30 C31 C36 -36.6(5) 2_576 . . . ?
N2 C30 C31 C36 154.3(3) . . . . ?
C36 C31 C32 C33 -2.1(5) . . . . ?
C30 C31 C32 C33 -177.2(3) . . . . ?
C31 C32 C33 C34 0.5(5) . . . . ?
C32 C33 C34 C35 1.3(5) . . . . ?
C32 C33 C34 C37 -178.2(3) . . . . ?
C33 C34 C35 C36 -1.4(5) . . . . ?
C37 C34 C35 C36 178.1(3) . . . . ?
C34 C35 C36 C31 -0.3(5) . . . . ?
C32 C31 C36 C35 2.0(5) . . . . ?
C30 C31 C36 C35 177.2(3) . . . . ?
C35 C34 C37 O7 -4.3(6) . . . . ?
C33 C34 C37 O7 175.2(4) . . . . ?
C35 C34 C37 O8 176.1(4) . . . . ?
C33 C34 C37 O8 -4.4(5) . . . . ?
C11 C10 N1 C9 0.2(4) . . . . ?
C12 C10 N1 C9 -173.5(3) . . . . ?
C11 C10 N1 C6 -166.5(4) . . . . ?
C12 C10 N1 C6 19.7(6) . . . . ?
C9 C9 N1 C10 -1.0(5) 2_676 . . . ?
C11 C9 N1 C10 -178.7(5) 2_676 . . . ?
C9 C9 N1 C6 167.1(4) 2_676 . . . ?
C11 C9 N1 C6 -10.6(7) 2_676 . . . ?
C7 C6 N1 C10 -134.1(4) . . . . ?
C5 C6 N1 C10 44.7(6) . . . . ?
C7 C6 N1 C9 60.7(5) . . . . ?
C5 C6 N1 C9 -120.5(4) . . . . ?
C28 C28 N2 C30 0.8(5) 2_576 . . . ?
C29 C28 N2 C30 179.3(4) . . . . ?
C28 C28 N2 C25 -167.4(3) 2_576 . . . ?
C29 C28 N2 C25 11.0(7) . . . . ?
C29 C30 N2 C28 -0.4(4) 2_576 . . . ?
C31 C30 N2 C28 170.6(3) . . . . ?
C29 C30 N2 C25 167.2(3) 2_576 . . . ?
C31 C30 N2 C25 -21.9(5) . . . . ?
C24 C25 N2 C28 -55.0(5) . . . . ?
C26 C25 N2 C28 124.9(4) . . . . ?
C24 C25 N2 C30 139.3(4) . . . . ?
C26 C25 N2 C30 -40.9(5) . . . . ?
O1 C2 O2 C1 -0.2(7) . . . . ?
C3 C2 O2 C1 178.9(4) . . . . ?
O3 C18 O4 C19 -0.8(8) . . . . ?
C15 C18 O4 C19 179.9(4) . . . . ?
O6 C21 O5 C20 1.5(7) . . . . ?
C22 C21 O5 C20 178.6(4) . . . . ?
O7 C37 O8 C38 -1.1(8) . . . . ?
C34 C37 O8 C38 178.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.17
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_exp_3408
_database_code_depnum_ccdc_archive 'CCDC 1544600'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 N2 O4'
_chemical_formula_weight         526.57

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   12.3284(6)
_cell_length_b                   6.1277(3)
_cell_length_c                   20.3379(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.907(5)
_cell_angle_gamma                90.00
_cell_volume                     1477.59(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5997
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2905
_reflns_number_gt                2191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0953P)²+0.1411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2905
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.09488(11) 0.4234(2) 0.09294(7) 0.0237(4) Uani 1 1 d . . .
O1 O 0.14937(12) 0.7717(3) 0.08705(8) 0.0297(4) Uani 1 1 d . . .
N1 N -0.38665(13) 0.8556(3) 0.05054(8) 0.0196(4) Uani 1 1 d . . .
C10 C -0.27129(16) 0.7984(4) 0.06084(10) 0.0206(5) Uani 1 1 d . . .
C12 C -0.12247(16) 0.5323(4) 0.08240(10) 0.0216(5) Uani 1 1 d . . .
H12 H -0.0975 0.3863 0.0923 0.026 Uiso 1 1 calc R . .
C13 C -0.04481(16) 0.6925(3) 0.07709(10) 0.0197(5) Uani 1 1 d . . .
C16 C 0.07599(16) 0.6391(4) 0.08621(10) 0.0204(5) Uani 1 1 d . . .
C15 C -0.19404(16) 0.9586(3) 0.05539(11) 0.0226(5) Uani 1 1 d . . .
H15 H -0.2185 1.1052 0.0463 0.027 Uiso 1 1 calc R . .
C1 C -0.44372(16) 1.0090(3) 0.00254(10) 0.0203(5) Uani 1 1 d . . .
C11 C -0.23517(16) 0.5821(4) 0.07348(10) 0.0203(5) Uani 1 1 d . . .
H11 H -0.2874 0.4705 0.0759 0.024 Uiso 1 1 calc R . .
C9 C -0.49786(17) 0.3890(4) 0.12406(11) 0.0250(5) Uani 1 1 d . . .
H9 H -0.5535 0.3589 0.0825 0.030 Uiso 1 1 calc R . .
C2 C -0.46816(16) 0.7481(3) 0.07538(11) 0.0221(5) Uani 1 1 d . . .
C4 C -0.43948(16) 0.5864(4) 0.13195(10) 0.0215(5) Uani 1 1 d . . .
C14 C -0.08183(16) 0.9063(4) 0.06312(11) 0.0227(5) Uani 1 1 d . . .
H14 H -0.0301 1.0167 0.0589 0.027 Uiso 1 1 calc R . .
C17 C 0.21051(16) 0.3550(4) 0.10336(11) 0.0251(5) Uani 1 1 d . . .
H17A H 0.2416 0.4241 0.0690 0.038 Uiso 1 1 calc R . .
H17B H 0.2133 0.1960 0.0989 0.038 Uiso 1 1 calc R . .
H17C H 0.2550 0.3986 0.1492 0.038 Uiso 1 1 calc R . .
C3 C -0.57330(16) 0.8306(4) 0.04429(11) 0.0210(5) Uani 1 1 d . . .
H3 H -0.6428 0.7892 0.0523 0.025 Uiso 1 1 calc R . .
C5 C -0.35658(18) 0.6268(4) 0.19279(11) 0.0278(5) Uani 1 1 d . . .
H5 H -0.3158 0.7602 0.1989 0.033 Uiso 1 1 calc R . .
C7 C -0.3935(2) 0.2771(4) 0.23652(13) 0.0402(6) Uani 1 1 d . . .
H7 H -0.3784 0.1720 0.2722 0.048 Uiso 1 1 calc R . .
C6 C -0.3336(2) 0.4706(4) 0.24481(12) 0.0366(6) Uani 1 1 d . . .
H6 H -0.2765 0.4975 0.2861 0.044 Uiso 1 1 calc R . .
C8 C -0.4755(2) 0.2371(4) 0.17605(12) 0.0331(6) Uani 1 1 d . . .
H8 H -0.5167 0.1042 0.1703 0.040 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
O2 C16 1.343(3) . ?
O2 C17 1.445(2) . ?
O1 C16 1.212(3) . ?
N1 C1 1.398(3) . ?
N1 C2 1.406(3) . ?
N1 C10 1.423(3) . ?
C10 C15 1.393(3) . ?
C10 C11 1.399(3) . ?
C12 C11 1.385(3) . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C16 1.486(3) . ?
C15 C14 1.386(3) . ?
C15 H15 0.9500 . ?
C1 C1 1.368(4) 3_475 ?
C1 C3 1.424(3) 3_475 ?
C11 H11 0.9500 . ?
C9 C8 1.379(3) . ?
C9 C4 1.394(3) . ?
C9 H9 0.9500 . ?
C2 C3 1.373(3) . ?
C2 C4 1.486(3) . ?
C4 C5 1.394(3) . ?
C14 H14 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C3 C1 1.424(3) 3_475 ?
C3 H3 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C7 C6 1.383(4) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C17 115.92(16) . . ?
C1 N1 C2 107.06(16) . . ?
C1 N1 C10 124.02(17) . . ?
C2 N1 C10 127.99(18) . . ?
C15 C10 C11 119.46(18) . . ?
C15 C10 N1 119.48(19) . . ?
C11 C10 N1 121.00(18) . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 118.99(18) . . ?
C14 C13 C16 119.64(18) . . ?
C12 C13 C16 121.38(19) . . ?
O1 C16 O2 123.38(18) . . ?
O1 C16 C13 124.9(2) . . ?
O2 C16 C13 111.68(17) . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C1 C1 N1 107.7(2) 3_475 . ?
C1 C1 C3 109.7(2) 3_475 3_475 ?
N1 C1 C3 142.48(18) . 3_475 ?
C12 C11 C10 119.34(19) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C8 C9 C4 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C3 C2 N1 109.85(18) . . ?
C3 C2 C4 126.60(19) . . ?
N1 C2 C4 123.28(17) . . ?
C9 C4 C5 119.1(2) . . ?
C9 C4 C2 118.92(18) . . ?
C5 C4 C2 121.99(19) . . ?
C15 C14 C13 120.15(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C3 C1 105.58(17) . 3_475 ?
C2 C3 H3 127.2 . . ?
C1 C3 H3 127.2 3_475 . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?

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
C1 N1 C10 C15 36.4(3) . . . . ?
C2 N1 C10 C15 -156.1(2) . . . . ?
C1 N1 C10 C11 -140.8(2) . . . . ?
C2 N1 C10 C11 26.7(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C16 -179.61(18) . . . . ?
C17 O2 C16 O1 1.6(3) . . . . ?
C17 O2 C16 C13 -178.91(15) . . . . ?
C14 C13 C16 O1 5.2(3) . . . . ?
C12 C13 C16 O1 -174.6(2) . . . . ?
C14 C13 C16 O2 -174.19(18) . . . . ?
C12 C13 C16 O2 6.0(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
N1 C10 C15 C14 -178.04(18) . . . . ?
C2 N1 C1 C1 -1.3(3) . . . 3_475 ?
C10 N1 C1 C1 168.4(2) . . . 3_475 ?
C2 N1 C1 C3 -177.9(3) . . . 3_475 ?
C10 N1 C1 C3 -8.2(4) . . . 3_475 ?
C13 C12 C11 C10 -1.9(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
N1 C10 C11 C12 179.20(17) . . . . ?
C1 N1 C2 C3 -0.1(2) . . . . ?
C10 N1 C2 C3 -169.23(19) . . . . ?
C1 N1 C2 C4 -174.41(19) . . . . ?
C10 N1 C2 C4 16.4(3) . . . . ?
C8 C9 C4 C5 1.1(3) . . . . ?
C8 C9 C4 C2 -178.42(19) . . . . ?
C3 C2 C4 C9 53.9(3) . . . . ?
N1 C2 C4 C9 -132.8(2) . . . . ?
C3 C2 C4 C5 -125.7(2) . . . . ?
N1 C2 C4 C5 47.7(3) . . . . ?
C10 C15 C14 C13 -0.6(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C16 C13 C14 C15 -179.16(18) . . . . ?
N1 C2 C3 C1 1.4(2) . . . 3_475 ?
C4 C2 C3 C1 175.5(2) . . . 3_475 ?
C9 C4 C5 C6 -0.3(3) . . . . ?
C2 C4 C5 C6 179.2(2) . . . . ?
C8 C7 C6 C5 0.8(4) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C4 C9 C8 C7 -1.0(3) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1544604'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H46 N2'
_chemical_formula_weight         578.81

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.144(8)
_cell_length_b                   8.484(6)
_cell_length_c                   17.017(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.58(2)
_cell_angle_gamma                90.00
_cell_volume                     1723(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1207
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.24

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10796
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.23
_reflns_number_total             3076
_reflns_number_gt                1844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0987P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3076
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9736(2) 0.0289(3) 0.71831(18) 0.0760(9) Uani 1 1 d . . .
H1A H 0.9538 0.1386 0.7161 0.114 Uiso 1 1 calc R . .
H1B H 0.9215 -0.0281 0.6792 0.114 Uiso 1 1 calc R . .
H1C H 1.0478 0.0167 0.7072 0.114 Uiso 1 1 calc R . .
C2 C 0.9698(2) -0.0352(3) 0.80101(16) 0.0572(7) Uani 1 1 d . . .
C3 C 1.0535(2) 0.0522(4) 0.8635(2) 0.0939(11) Uani 1 1 d . . .
H3A H 1.0295 0.1593 0.8671 0.141 Uiso 1 1 calc R . .
H3B H 1.1259 0.0506 0.8485 0.141 Uiso 1 1 calc R . .
H3C H 1.0579 0.0017 0.9145 0.141 Uiso 1 1 calc R . .
C4 C 0.85433(19) -0.0310(3) 0.82394(14) 0.0468(6) Uani 1 1 d . . .
C5 C 0.8198(2) -0.1507(3) 0.86955(14) 0.0525(6) Uani 1 1 d . . .
H5 H 0.8661 -0.2375 0.8831 0.063 Uiso 1 1 calc R . .
C6 C 0.71840(19) -0.1445(3) 0.89539(14) 0.0508(6) Uani 1 1 d . . .
H6 H 0.6972 -0.2274 0.9251 0.061 Uiso 1 1 calc R . .
C7 C 0.64805(18) -0.0157(3) 0.87734(12) 0.0433(6) Uani 1 1 d . . .
C8 C 0.68021(19) 0.1038(3) 0.83137(14) 0.0518(6) Uani 1 1 d . . .
H8 H 0.6337 0.1906 0.8181 0.062 Uiso 1 1 calc R . .
C9 C 0.7814(2) 0.0953(3) 0.80479(15) 0.0540(6) Uani 1 1 d . . .
H9 H 0.8010 0.1764 0.7733 0.065 Uiso 1 1 calc R . .
C10 C 0.54928(18) -0.0273(3) 0.99119(13) 0.0456(6) Uani 1 1 d . . .
C11 C 0.38237(19) 0.0818(3) 0.93755(13) 0.0473(6) Uani 1 1 d . . .
H11 H 0.3105 0.1233 0.9322 0.057 Uiso 1 1 calc R . .
C12 C 0.44369(18) 0.0611(3) 0.87754(13) 0.0454(6) Uani 1 1 d . . .
C13 C 0.40334(18) 0.0871(3) 0.79244(13) 0.0436(6) Uani 1 1 d . . .
C14 C 0.4372(2) -0.0045(3) 0.73295(14) 0.0547(7) Uani 1 1 d . . .
H14 H 0.4907 -0.0827 0.7475 0.066 Uiso 1 1 calc R . .
C15 C 0.3931(2) 0.0181(3) 0.65308(14) 0.0575(7) Uani 1 1 d . . .
H15 H 0.4186 -0.0441 0.6151 0.069 Uiso 1 1 calc R . .
C16 C 0.3119(2) 0.1312(3) 0.62788(14) 0.0512(6) Uani 1 1 d . . .
C17 C 0.27710(19) 0.2210(3) 0.68681(14) 0.0525(6) Uani 1 1 d . . .
H17 H 0.2219 0.2969 0.6720 0.063 Uiso 1 1 calc R . .
C18 C 0.32170(18) 0.2011(3) 0.76647(14) 0.0499(6) Uani 1 1 d . . .
H18 H 0.2969 0.2652 0.8040 0.060 Uiso 1 1 calc R . .
C19 C 0.2597(2) 0.1581(4) 0.54033(15) 0.0680(8) Uani 1 1 d . . .
C20 C 0.1423(3) 0.0945(5) 0.52202(19) 0.1085(13) Uani 1 1 d . . .
H20A H 0.1091 0.1199 0.4679 0.163 Uiso 1 1 calc R . .
H20B H 0.0988 0.1408 0.5578 0.163 Uiso 1 1 calc R . .
H20C H 0.1439 -0.0179 0.5287 0.163 Uiso 1 1 calc R . .
C21 C 0.3307(3) 0.0987(5) 0.48279(19) 0.1157(14) Uani 1 1 d . . .
H21A H 0.3399 -0.0133 0.4886 0.174 Uiso 1 1 calc R . .
H21B H 0.4028 0.1488 0.4940 0.174 Uiso 1 1 calc R . .
H21C H 0.2948 0.1228 0.4291 0.174 Uiso 1 1 calc R . .
N1 N 0.54774(15) -0.0065(2) 0.91007(10) 0.0463(5) Uani 1 1 d . . .
H2 H 0.991(2) -0.152(3) 0.8014(14) 0.072(8) Uiso 1 1 d . . .
H19 H 0.255(3) 0.275(4) 0.5328(18) 0.099(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.517(4) . ?
C2 C3 1.522(4) . ?
C2 C4 1.523(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.391(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.380(3) . ?
C7 N1 1.432(3) . ?
C8 C9 1.387(3) . ?
C10 C10 1.367(4) 3_657 ?
C10 N1 1.388(3) . ?
C10 C11 1.415(3) 3_657 ?
C11 C12 1.381(3) . ?
C11 C10 1.415(3) 3_657 ?
C12 N1 1.405(3) . ?
C12 C13 1.458(3) . ?
C13 C14 1.396(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.385(3) . ?
C16 C19 1.525(3) . ?
C17 C18 1.375(3) . ?
C19 C20 1.503(4) . ?
C19 C21 1.505(4) . ?

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
C3 C2 C1 110.1(3) . . ?
C3 C2 C4 109.7(2) . . ?
C1 C2 C4 114.5(2) . . ?
C5 C4 C9 116.7(2) . . ?
C5 C4 C2 120.9(2) . . ?
C9 C4 C2 122.3(2) . . ?
C6 C5 C4 121.9(2) . . ?
C5 C6 C7 120.5(2) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 N1 122.0(2) . . ?
C6 C7 N1 119.4(2) . . ?
C7 C8 C9 120.4(2) . . ?
C8 C9 C4 121.9(2) . . ?
C10 C10 N1 108.8(2) 3_657 . ?
C10 C10 C11 108.8(2) 3_657 3_657 ?
N1 C10 C11 142.4(2) . 3_657 ?
C12 C11 C10 106.3(2) . 3_657 ?
C11 C12 N1 109.18(19) . . ?
C11 C12 C13 125.9(2) . . ?
N1 C12 C13 124.5(2) . . ?
C14 C13 C18 116.2(2) . . ?
C14 C13 C12 123.1(2) . . ?
C18 C13 C12 120.6(2) . . ?
C15 C14 C13 121.6(2) . . ?
C14 C15 C16 121.7(2) . . ?
C17 C16 C15 116.8(2) . . ?
C17 C16 C19 119.9(2) . . ?
C15 C16 C19 123.3(2) . . ?
C18 C17 C16 122.0(2) . . ?
C17 C18 C13 121.6(2) . . ?
C20 C19 C21 112.3(3) . . ?
C20 C19 C16 110.9(2) . . ?
C21 C19 C16 113.6(3) . . ?
C10 N1 C12 106.89(17) . . ?
C10 N1 C7 121.53(17) . . ?
C12 N1 C7 129.54(18) . . ?

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
C3 C2 C4 C5 -91.7(3) . . . . ?
C1 C2 C4 C5 143.9(2) . . . . ?
C3 C2 C4 C9 84.5(3) . . . . ?
C1 C2 C4 C9 -40.0(3) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C2 C4 C5 C6 175.8(2) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C5 C6 C7 N1 -175.1(2) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
N1 C7 C8 C9 176.0(2) . . . . ?
C7 C8 C9 C4 -0.9(4) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
C2 C4 C9 C8 -174.8(2) . . . . ?
C10 C11 C12 N1 0.6(3) 3_657 . . . ?
C10 C11 C12 C13 174.0(2) 3_657 . . . ?
C11 C12 C13 C14 -145.2(2) . . . . ?
N1 C12 C13 C14 27.2(3) . . . . ?
C11 C12 C13 C18 30.6(3) . . . . ?
N1 C12 C13 C18 -157.0(2) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C15 176.7(2) . . . . ?
C13 C14 C15 C16 -1.0(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C14 C15 C16 C19 -179.0(3) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C19 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C13 -1.2(4) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C12 C13 C18 C17 -175.7(2) . . . . ?
C17 C16 C19 C20 -73.2(4) . . . . ?
C15 C16 C19 C20 105.9(3) . . . . ?
C17 C16 C19 C21 159.1(3) . . . . ?
C15 C16 C19 C21 -21.8(4) . . . . ?
C10 C10 N1 C12 -0.9(3) 3_657 . . . ?
C11 C10 N1 C12 -178.9(3) 3_657 . . . ?
C10 C10 N1 C7 164.3(2) 3_657 . . . ?
C11 C10 N1 C7 -13.7(4) 3_657 . . . ?
C11 C12 N1 C10 0.1(2) . . . . ?
C13 C12 N1 C10 -173.3(2) . . . . ?
C11 C12 N1 C7 -163.5(2) . . . . ?
C13 C12 N1 C7 23.1(4) . . . . ?
C8 C7 N1 C10 -126.1(2) . . . . ?
C6 C7 N1 C10 50.5(3) . . . . ?
C8 C7 N1 C12 35.4(3) . . . . ?
C6 C7 N1 C12 -147.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_exp_3317
_database_code_depnum_ccdc_archive 'CCDC 1544598'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_audit_creation_date             2015-06-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C16 H10 N2)'
_chemical_formula_sum            'C32 H20 N4'
_chemical_formula_weight         460.52
_chemical_melting_point          ?
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'

_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                   6.0244(7)
_cell_length_b                   9.5199(11)
_cell_length_c                   10.6867(14)
_cell_angle_alpha                97.209(10)
_cell_angle_beta                 98.460(10)
_cell_angle_gamma                102.006(10)
_cell_volume                     585.20(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    839
_cell_measurement_temperature    102.4
_cell_measurement_theta_max      29.5482
_cell_measurement_theta_min      3.1753
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3754
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      102.4
_diffrn_detector_area_resol_mean 16.0971
_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   -8.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000    0.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0485447000
_diffrn_orient_matrix_UB_12      -0.0150650000
_diffrn_orient_matrix_UB_13      -0.0662383000
_diffrn_orient_matrix_UB_21      0.0395392000
_diffrn_orient_matrix_UB_22      -0.0652880000
_diffrn_orient_matrix_UB_23      -0.0059898000
_diffrn_orient_matrix_UB_31      -0.1051332000
_diffrn_orient_matrix_UB_32      -0.0382990000
_diffrn_orient_matrix_UB_33      0.0141770000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1746
_reflns_number_total             2302
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.037
_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)+(0.0405P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1101
_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. 
;
_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
N1 N 0.0395(2) 0.35108(15) 0.90334(14) 0.0173(3) Uani 1 1 d . . .
C7 C 0.5873(3) 0.35769(19) 0.56924(17) 0.0192(4) Uani 1 1 d . . .
C5 C 0.2401(3) 0.30555(18) 0.65726(17) 0.0190(4) Uani 1 1 d . . .
H5 H 0.0898 0.2521 0.6510 0.023 Uiso 1 1 calc R . .
C10 C 0.7136(3) 0.32826(19) 0.46765(18) 0.0208(4) Uani 1 1 d . . .
C6 C 0.3625(3) 0.27730(19) 0.56100(17) 0.0205(4) Uani 1 1 d . . .
H6 H 0.2952 0.2049 0.4910 0.025 Uiso 1 1 calc R . .
N2 N 0.8118(3) 0.30267(17) 0.38689(16) 0.0270(4) Uani 1 1 d . . .
C4 C 0.3390(3) 0.41366(18) 0.76424(17) 0.0169(4) Uani 1 1 d . . .
C11 C -0.0224(3) 0.19624(18) 0.86667(17) 0.0183(4) Uani 1 1 d . . .
C9 C 0.5648(3) 0.49301(18) 0.76996(17) 0.0181(4) Uani 1 1 d . . .
H9 H 0.6330 0.5651 0.8401 0.022 Uiso 1 1 calc R . .
C8 C 0.6883(3) 0.46686(18) 0.67426(17) 0.0193(4) Uani 1 1 d . . .
H8 H 0.8376 0.5214 0.6795 0.023 Uiso 1 1 calc R . .
C2 C 0.2115(3) 0.45119(18) 0.86489(16) 0.0173(4) Uani 1 1 d . . .
C12 C 0.1443(3) 0.1157(2) 0.88328(18) 0.0230(4) Uani 1 1 d . . .
H12 H 0.2956 0.1613 0.9211 0.028 Uiso 1 1 calc R . .
C16 C -0.2487(3) 0.1292(2) 0.81445(17) 0.0232(4) Uani 1 1 d . . .
H16 H -0.3598 0.1836 0.8050 0.028 Uiso 1 1 calc R . .
C13 C 0.0822(4) -0.0331(2) 0.84281(19) 0.0292(5) Uani 1 1 d . . .
H13 H 0.1931 -0.0878 0.8518 0.035 Uiso 1 1 calc R . .
C3 C 0.2236(3) 0.58978(18) 0.92901(17) 0.0182(4) Uani 1 1 d . . .
H3 H 0.3220 0.6762 0.9212 0.022 Uiso 1 1 calc R . .
C15 C -0.3088(3) -0.0213(2) 0.77594(19) 0.0313(5) Uani 1 1 d . . .
H15 H -0.4611 -0.0677 0.7413 0.038 Uiso 1 1 calc R . .
C14 C -0.1440(4) -0.1011(2) 0.7890(2) 0.0343(5) Uani 1 1 d . . .
H14 H -0.1844 -0.2012 0.7617 0.041 Uiso 1 1 calc R . .
C1 C -0.0560(3) 0.42786(18) 0.99173(17) 0.0175(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.431(2) . ?
N1 C2 1.401(2) . ?
N1 C1 1.385(2) . ?
C7 C10 1.446(2) . ?
C7 C6 1.394(2) . ?
C7 C8 1.398(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C5 C4 1.404(2) . ?
C10 N2 1.145(2) . ?
C6 H6 0.9300 . ?
C4 C9 1.400(2) . ?
C4 C2 1.461(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.379(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.378(2) . ?
C8 H8 0.9300 . ?
C2 C3 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.394(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C1 1.408(2) 2_567 ?
C15 H15 0.9300 . ?
C15 C14 1.373(3) . ?
C14 H14 0.9300 . ?
C1 C3 1.408(2) 2_567 ?
C1 C1 1.375(3) 2_567 ?

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 C11 127.83(13) . . ?
C1 N1 C11 124.52(14) . . ?
C1 N1 C2 107.54(13) . . ?
C6 C7 C10 119.47(16) . . ?
C6 C7 C8 120.12(15) . . ?
C8 C7 C10 120.41(15) . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 121.03(16) . . ?
C4 C5 H5 119.5 . . ?
N2 C10 C7 178.90(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.80(16) . . ?
C5 C6 H6 120.1 . . ?
C5 C4 C2 122.59(15) . . ?
C9 C4 C5 117.99(15) . . ?
C9 C4 C2 119.33(15) . . ?
C12 C11 N1 120.09(16) . . ?
C16 C11 N1 118.99(15) . . ?
C16 C11 C12 120.92(16) . . ?
C4 C9 H9 119.2 . . ?
C8 C9 C4 121.63(16) . . ?
C8 C9 H9 119.2 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.43(16) . . ?
C9 C8 H8 120.3 . . ?
N1 C2 C4 123.92(15) . . ?
C3 C2 N1 109.12(14) . . ?
C3 C2 C4 126.72(16) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.06(18) . . ?
C13 C12 H12 120.5 . . ?
C11 C16 H16 120.4 . . ?
C11 C16 C15 119.19(18) . . ?
C15 C16 H16 120.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.39(18) . . ?
C14 C13 H13 119.8 . . ?
C2 C3 H3 127.1 . . ?
C2 C3 C1 105.76(15) . 2_567 ?
C1 C3 H3 127.1 2_567 . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.24(19) . . ?
C14 C15 H15 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.16(18) . . ?
C15 C14 H14 119.9 . . ?
N1 C1 C3 142.43(15) . 2_567 ?
C1 C1 N1 107.95(17) 2_567 . ?
C1 C1 C3 109.62(17) 2_567 2_567 ?

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
N1 C11 C12 C13 -177.65(16) . . . . ?
N1 C11 C16 C15 178.58(16) . . . . ?
N1 C2 C3 C1 0.4(2) . . . 2_567 ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C5 C4 C2 N1 32.7(3) . . . . ?
C5 C4 C2 C3 -141.15(19) . . . . ?
C10 C7 C6 C5 -179.52(17) . . . . ?
C10 C7 C8 C9 -179.98(16) . . . . ?
C6 C7 C10 N2 -32(11) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C6 C5 C4 C9 0.6(3) . . . . ?
C6 C5 C4 C2 177.11(17) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C9 C8 C7 -0.6(3) . . . . ?
C4 C2 C3 C1 174.93(17) . . . 2_567 ?
C11 N1 C2 C4 8.9(3) . . . . ?
C11 N1 C2 C3 -176.41(17) . . . . ?
C11 N1 C1 C3 -2.8(4) . . . 2_567 ?
C11 N1 C1 C1 176.14(19) . . . 2_567 ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C11 C16 C15 C14 -0.5(3) . . . . ?
C9 C4 C2 N1 -150.87(17) . . . . ?
C9 C4 C2 C3 35.3(3) . . . . ?
C8 C7 C10 N2 149(10) . . . . ?
C8 C7 C6 C5 -0.2(3) . . . . ?
C2 N1 C11 C12 54.3(3) . . . . ?
C2 N1 C11 C16 -125.38(19) . . . . ?
C2 N1 C1 C3 -179.4(2) . . . 2_567 ?
C2 N1 C1 C1 -0.5(2) . . . 2_567 ?
C2 C4 C9 C8 -176.71(16) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
C16 C15 C14 C13 1.2(3) . . . . ?
C1 N1 C11 C12 -121.56(19) . . . . ?
C1 N1 C11 C16 58.7(2) . . . . ?
C1 N1 C2 C4 -174.70(16) . . . . ?
C1 N1 C2 C3 0.0(2) . . . . ?

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1544603'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H34 N2'
_chemical_formula_weight         494.65

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.0988(12)
_cell_length_b                   11.519(2)
_cell_length_c                   11.831(2)
_cell_angle_alpha                116.842(5)
_cell_angle_beta                 104.607(6)
_cell_angle_gamma                91.839(6)
_cell_volume                     707.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    670
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      19.83

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4565
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2461
_reflns_number_gt                1460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0853P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2461
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2125(5) 0.4417(3) 0.1472(2) 0.0611(7) Uani 1 1 d . . .
H1 H 0.0815 0.4803 0.1406 0.073 Uiso 1 1 calc R . .
C2 C 0.3200(6) 0.4067(3) 0.0502(3) 0.0725(9) Uani 1 1 d . . .
H2 H 0.2631 0.4237 -0.0206 0.087 Uiso 1 1 calc R . .
C3 C 0.5103(6) 0.3471(3) 0.0567(3) 0.0716(9) Uani 1 1 d . . .
H3 H 0.5812 0.3232 -0.0097 0.086 Uiso 1 1 calc R . .
C4 C 0.5959(5) 0.3228(3) 0.1612(3) 0.0665(8) Uani 1 1 d . . .
H4 H 0.7247 0.2820 0.1655 0.080 Uiso 1 1 calc R . .
C5 C 0.4912(5) 0.3586(2) 0.2597(2) 0.0545(7) Uani 1 1 d . . .
H5 H 0.5501 0.3418 0.3304 0.065 Uiso 1 1 calc R . .
C6 C 0.2980(4) 0.4198(2) 0.2551(2) 0.0484(6) Uani 1 1 d . . .
C7 C 0.1878(4) 0.4529(2) 0.3600(2) 0.0484(6) Uani 1 1 d . . .
C8 C -0.0288(4) 0.5539(2) 0.4926(2) 0.0468(6) Uani 1 1 d . . .
C9 C -0.1635(4) 0.6180(2) 0.5750(2) 0.0503(6) Uani 1 1 d . . .
H9 H -0.2246 0.6935 0.5840 0.060 Uiso 1 1 calc R . .
C10 C 0.0671(4) 0.6668(2) 0.3722(2) 0.0458(6) Uani 1 1 d . . .
C11 C -0.1399(5) 0.6977(2) 0.3255(2) 0.0530(7) Uani 1 1 d . . .
H11 H -0.2764 0.6481 0.3120 0.064 Uiso 1 1 calc R . .
C12 C -0.1455(5) 0.8026(3) 0.2984(3) 0.0594(7) Uani 1 1 d . . .
H12 H -0.2869 0.8234 0.2679 0.071 Uiso 1 1 calc R . .
C13 C 0.0548(5) 0.8778(2) 0.3156(2) 0.0565(7) Uani 1 1 d . . .
C14 C 0.2598(5) 0.8441(3) 0.3632(3) 0.0634(7) Uani 1 1 d . . .
H14 H 0.3970 0.8925 0.3759 0.076 Uiso 1 1 calc R . .
C15 C 0.2681(5) 0.7416(2) 0.3924(2) 0.0586(7) Uani 1 1 d . . .
H15 H 0.4092 0.7225 0.4258 0.070 Uiso 1 1 calc R . .
C16 C 0.0547(7) 0.9889(3) 0.2806(3) 0.0804(10) Uani 1 1 d . . .
H16 H 0.178(6) 1.065(3) 0.354(3) 0.097 Uiso 1 1 d . . .
C17 C -0.1673(7) 1.0405(3) 0.2683(4) 0.1092(13) Uani 1 1 d . . .
H17A H -0.2830 0.9749 0.1910 0.164 Uiso 1 1 calc R . .
H17B H -0.1470 1.1191 0.2602 0.164 Uiso 1 1 calc R . .
H17C H -0.2143 1.0605 0.3458 0.164 Uiso 1 1 calc R . .
C18 C 0.1252(9) 0.9488(5) 0.1556(5) 0.1403(19) Uani 1 1 d . . .
H18A H 0.0058 0.8834 0.0804 0.210 Uiso 1 1 calc R . .
H18B H 0.2647 0.9128 0.1636 0.210 Uiso 1 1 calc R . .
H18C H 0.1497 1.0247 0.1436 0.210 Uiso 1 1 calc R . .
N1 N 0.0700(3) 0.55963(18) 0.40131(18) 0.0491(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.370(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.377(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.465(3) . ?
C7 C9 1.377(3) 2_566 ?
C7 N1 1.399(3) . ?
C8 C8 1.374(4) 2_566 ?
C8 N1 1.387(3) . ?
C8 C9 1.401(3) . ?
C9 C7 1.377(3) 2_566 ?
C10 C11 1.371(3) . ?
C10 C15 1.379(3) . ?
C10 N1 1.423(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.390(4) . ?
C13 C14 1.380(4) . ?
C13 C16 1.513(3) . ?
C14 C15 1.371(3) . ?
C16 C17 1.496(5) . ?
C16 C18 1.518(4) . ?

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 C1 C6 120.5(3) . . ?
C3 C2 C1 120.6(3) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C5 C6 120.9(2) . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C7 119.2(2) . . ?
C9 C7 N1 108.90(19) 2_566 . ?
C9 C7 C6 127.6(2) 2_566 . ?
N1 C7 C6 123.33(19) . . ?
C8 C8 N1 107.6(2) 2_566 . ?
C8 C8 C9 109.3(2) 2_566 . ?
N1 C8 C9 143.0(2) . . ?
C7 C9 C8 106.5(2) 2_566 . ?
C11 C10 C15 119.4(2) . . ?
C11 C10 N1 119.3(2) . . ?
C15 C10 N1 121.3(2) . . ?
C10 C11 C12 120.0(2) . . ?
C11 C12 C13 121.6(3) . . ?
C14 C13 C12 116.8(2) . . ?
C14 C13 C16 120.2(3) . . ?
C12 C13 C16 123.0(3) . . ?
C15 C14 C13 122.2(2) . . ?
C14 C15 C10 120.0(2) . . ?
C17 C16 C13 114.3(3) . . ?
C17 C16 C18 110.4(3) . . ?
C13 C16 C18 110.8(3) . . ?
C8 N1 C7 107.58(17) . . ?
C8 N1 C10 123.12(18) . . ?
C7 N1 C10 128.91(18) . . ?

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
C6 C1 C2 C3 1.4(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C1 C6 C7 C9 141.4(3) . . . 2_566 ?
C5 C6 C7 C9 -35.7(4) . . . 2_566 ?
C1 C6 C7 N1 -32.5(4) . . . . ?
C5 C6 C7 N1 150.4(2) . . . . ?
C8 C8 C9 C7 -0.2(3) 2_566 . . 2_566 ?
N1 C8 C9 C7 -179.7(3) . . . 2_566 ?
C15 C10 C11 C12 0.3(3) . . . . ?
N1 C10 C11 C12 179.15(19) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C11 C12 C13 C16 176.9(2) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C16 C13 C14 C15 -178.0(2) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C11 C10 C15 C14 -1.3(4) . . . . ?
N1 C10 C15 C14 179.9(2) . . . . ?
C14 C13 C16 C17 -163.3(3) . . . . ?
C12 C13 C16 C17 18.8(4) . . . . ?
C14 C13 C16 C18 71.2(4) . . . . ?
C12 C13 C16 C18 -106.7(4) . . . . ?
C8 C8 N1 C7 0.4(3) 2_566 . . . ?
C9 C8 N1 C7 179.8(3) . . . . ?
C8 C8 N1 C10 -173.0(3) 2_566 . . . ?
C9 C8 N1 C10 6.4(5) . . . . ?
C9 C7 N1 C8 -0.2(3) 2_566 . . . ?
C6 C7 N1 C8 174.7(2) . . . . ?
C9 C7 N1 C10 172.6(2) 2_566 . . . ?
C6 C7 N1 C10 -12.5(4) . . . . ?
C11 C10 N1 C8 -58.7(3) . . . . ?
C15 C10 N1 C8 120.1(3) . . . . ?
C11 C10 N1 C7 129.4(3) . . . . ?
C15 C10 N1 C7 -51.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1544602'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H38 N2 O4'
_chemical_formula_weight         610.72

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.068(4)
_cell_length_b                   12.768(5)
_cell_length_c                   15.473(6)
_cell_angle_alpha                75.908(7)
_cell_angle_beta                 78.601(8)
_cell_angle_gamma                75.752(7)
_cell_volume                     1666.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    952
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      19.77

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9060
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.1948
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5836
_reflns_number_gt                2505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5836
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2919
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4231(13) 0.0812(6) 0.2385(5) 0.192(5) Uani 1 1 d . . .
H1A H 0.4894 0.0261 0.2081 0.288 Uiso 1 1 calc R . .
H1B H 0.4346 0.1532 0.2046 0.288 Uiso 1 1 calc R . .
H1C H 0.3183 0.0748 0.2441 0.288 Uiso 1 1 calc R . .
C2 C 0.4640(9) 0.0657(5) 0.3274(4) 0.097(2) Uani 1 1 d . . .
H2 H 0.587(7) 0.050(5) 0.317(4) 0.116 Uiso 1 1 d . . .
C3 C 0.4513(12) -0.0370(5) 0.3890(5) 0.167(4) Uani 1 1 d . . .
H3A H 0.3466 -0.0455 0.3998 0.251 Uiso 1 1 calc R . .
H3B H 0.4824 -0.0371 0.4449 0.251 Uiso 1 1 calc R . .
H3C H 0.5165 -0.0969 0.3636 0.251 Uiso 1 1 calc R . .
C4 C 0.4044(7) 0.1685(4) 0.3676(3) 0.0738(15) Uani 1 1 d . . .
C5 C 0.2637(7) 0.1879(4) 0.4231(3) 0.0720(14) Uani 1 1 d . . .
H5 H 0.2024 0.1357 0.4366 0.086 Uiso 1 1 calc R . .
C6 C 0.2125(6) 0.2814(4) 0.4587(3) 0.0672(13) Uani 1 1 d . . .
H6 H 0.1174 0.2915 0.4950 0.081 Uiso 1 1 calc R . .
C7 C 0.3016(6) 0.3614(4) 0.4408(3) 0.0627(12) Uani 1 1 d . . .
C8 C 0.4433(6) 0.3427(4) 0.3855(3) 0.0760(15) Uani 1 1 d . . .
H8 H 0.5060 0.3938 0.3730 0.091 Uiso 1 1 calc R . .
C9 C 0.4909(7) 0.2493(4) 0.3492(3) 0.0811(16) Uani 1 1 d . . .
H9 H 0.5842 0.2400 0.3112 0.097 Uiso 1 1 calc R . .
C10 C 0.2491(6) 0.4565(4) 0.4853(3) 0.0652(13) Uani 1 1 d . . .
C11 C 0.1813(6) 0.4541(4) 0.5728(3) 0.0715(14) Uani 1 1 d . . .
H11 H 0.1485 0.3943 0.6129 0.086 Uiso 1 1 calc R . .
C12 C 0.1703(6) 0.5583(4) 0.5910(3) 0.0645(13) Uani 1 1 d . . .
C13 C 0.2285(6) 0.6251(4) 0.5133(3) 0.0632(13) Uani 1 1 d . . .
C14 C 0.2015(6) 0.7326(4) 0.5281(3) 0.0687(14) Uani 1 1 d . . .
H14 H 0.2262 0.7940 0.4863 0.082 Uiso 1 1 calc R . .
C15 C 0.1313(6) 0.7306(4) 0.6162(3) 0.0630(13) Uani 1 1 d . . .
C16 C 0.0930(6) 0.8224(4) 0.6632(3) 0.0619(12) Uani 1 1 d . . .
C17 C 0.0893(6) 0.8103(4) 0.7557(3) 0.0659(13) Uani 1 1 d . . .
H17 H 0.1096 0.7399 0.7915 0.079 Uiso 1 1 calc R . .
C18 C 0.0558(7) 0.9020(4) 0.7950(3) 0.0774(16) Uani 1 1 d . . .
H18 H 0.0518 0.8911 0.8570 0.093 Uiso 1 1 calc R . .
C19 C 0.0283(7) 1.0090(4) 0.7452(3) 0.0762(15) Uani 1 1 d . . .
C20 C 0.0340(7) 1.0212(4) 0.6527(3) 0.0826(16) Uani 1 1 d . . .
H20 H 0.0160 1.0917 0.6168 0.099 Uiso 1 1 calc R . .
C21 C 0.0656(7) 0.9310(4) 0.6137(3) 0.0740(15) Uani 1 1 d . . .
H21 H 0.0690 0.9425 0.5516 0.089 Uiso 1 1 calc R . .
C22 C -0.0078(10) 1.1097(5) 0.7863(4) 0.104(2) Uani 1 1 d . . .
H22 H -0.042(9) 1.166(5) 0.745(4) 0.125 Uiso 1 1 d . . .
C23 C 0.1273(11) 1.1658(7) 0.7632(6) 0.187(5) Uani 1 1 d . . .
H23A H 0.0928 1.2410 0.7703 0.280 Uiso 1 1 calc R . .
H23B H 0.1735 1.1643 0.7020 0.280 Uiso 1 1 calc R . .
H23C H 0.2017 1.1278 0.8027 0.280 Uiso 1 1 calc R . .
C24 C -0.0796(11) 1.0963(6) 0.8806(4) 0.144(3) Uani 1 1 d . . .
H24A H -0.0096 1.0445 0.9177 0.216 Uiso 1 1 calc R . .
H24B H -0.1719 1.0692 0.8875 0.216 Uiso 1 1 calc R . .
H24C H -0.1042 1.1662 0.8985 0.216 Uiso 1 1 calc R . .
C25 C 0.3355(6) 0.6068(4) 0.3582(3) 0.0629(13) Uani 1 1 d . . .
C26 C 0.2842(6) 0.5884(4) 0.2850(3) 0.0714(14) Uani 1 1 d . . .
H26 H 0.2116 0.5450 0.2942 0.086 Uiso 1 1 calc R . .
C27 C 0.3425(7) 0.6353(4) 0.1986(3) 0.0771(15) Uani 1 1 d . . .
H27 H 0.3080 0.6227 0.1501 0.092 Uiso 1 1 calc R . .
C28 C 0.4504(6) 0.7005(4) 0.1820(3) 0.0699(14) Uani 1 1 d . . .
C29 C 0.5007(6) 0.7193(4) 0.2554(3) 0.0739(14) Uani 1 1 d . . .
H29 H 0.5726 0.7633 0.2460 0.089 Uiso 1 1 calc R . .
C30 C 0.4432(6) 0.6721(4) 0.3428(3) 0.0703(14) Uani 1 1 d . . .
H30 H 0.4776 0.6846 0.3914 0.084 Uiso 1 1 calc R . .
C31 C 0.5102(8) 0.7476(5) 0.0887(4) 0.0865(17) Uani 1 1 d . . .
C32 C 0.6866(10) 0.8506(6) -0.0068(4) 0.149(3) Uani 1 1 d . . .
H32A H 0.7305 0.7928 -0.0398 0.223 Uiso 1 1 calc R . .
H32B H 0.7657 0.8863 -0.0025 0.223 Uiso 1 1 calc R . .
H32C H 0.6089 0.9035 -0.0375 0.223 Uiso 1 1 calc R . .
C33 C 0.0404(6) 0.5769(4) 0.7418(3) 0.0600(12) Uani 1 1 d . . .
C34 C 0.1180(7) 0.4794(4) 0.7892(3) 0.0698(14) Uani 1 1 d . . .
H34 H 0.2164 0.4475 0.7652 0.084 Uiso 1 1 calc R . .
C35 C 0.0504(7) 0.4289(4) 0.8723(3) 0.0696(14) Uani 1 1 d . . .
H35 H 0.1028 0.3624 0.9028 0.083 Uiso 1 1 calc R . .
C36 C -0.0942(6) 0.4767(4) 0.9100(3) 0.0625(13) Uani 1 1 d . . .
C37 C -0.1711(6) 0.5756(4) 0.8629(3) 0.0686(13) Uani 1 1 d . . .
H37 H -0.2683 0.6088 0.8876 0.082 Uiso 1 1 calc R . .
C38 C -0.1041(6) 0.6252(4) 0.7792(3) 0.0664(13) Uani 1 1 d . . .
H38 H -0.1566 0.6914 0.7483 0.080 Uiso 1 1 calc R . .
C39 C -0.1617(8) 0.4164(5) 0.9963(3) 0.0725(14) Uani 1 1 d . . .
C40 C -0.3836(7) 0.4113(5) 1.1074(3) 0.0957(18) Uani 1 1 d . . .
H40A H -0.3868 0.3391 1.1008 0.143 Uiso 1 1 calc R . .
H40B H -0.4865 0.4529 1.1189 0.143 Uiso 1 1 calc R . .
H40C H -0.3303 0.4045 1.1570 0.143 Uiso 1 1 calc R . .
N1 N 0.2787(5) 0.5621(3) 0.4476(2) 0.0665(11) Uani 1 1 d . . .
N2 N 0.1113(5) 0.6223(3) 0.6554(2) 0.0661(11) Uani 1 1 d . . .
O1 O 0.4705(6) 0.7349(4) 0.0228(3) 0.1269(18) Uani 1 1 d . . .
O2 O 0.6183(6) 0.8037(4) 0.0832(2) 0.1133(15) Uani 1 1 d . . .
O3 O -0.0984(5) 0.3307(3) 1.0383(2) 0.0968(13) Uani 1 1 d . . .
O4 O -0.3037(5) 0.4676(3) 1.0256(2) 0.0866(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.449(9) . ?
C2 C3 1.436(9) . ?
C2 C4 1.523(7) . ?
C4 C9 1.388(7) . ?
C4 C5 1.394(7) . ?
C5 C6 1.374(6) . ?
C6 C7 1.397(7) . ?
C7 C8 1.398(7) . ?
C7 C10 1.473(6) . ?
C8 C9 1.379(6) . ?
C10 C11 1.368(6) . ?
C10 N1 1.401(6) . ?
C11 C12 1.402(6) . ?
C12 N2 1.385(5) . ?
C12 C13 1.386(6) . ?
C13 N1 1.386(5) . ?
C13 C14 1.401(6) . ?
C14 C15 1.383(6) . ?
C15 N2 1.409(6) . ?
C15 C16 1.462(6) . ?
C16 C17 1.397(6) . ?
C16 C21 1.400(6) . ?
C17 C18 1.390(6) . ?
C18 C19 1.386(7) . ?
C19 C20 1.393(7) . ?
C19 C22 1.507(7) . ?
C20 C21 1.372(6) . ?
C22 C24 1.463(8) . ?
C22 C23 1.509(11) . ?
C25 C30 1.384(7) . ?
C25 C26 1.396(6) . ?
C25 N1 1.409(5) . ?
C26 C27 1.382(6) . ?
C27 C28 1.383(7) . ?
C28 C29 1.395(6) . ?
C28 C31 1.473(7) . ?
C29 C30 1.394(6) . ?
C31 O1 1.204(6) . ?
C31 O2 1.328(7) . ?
C32 O2 1.456(6) . ?
C33 C38 1.382(7) . ?
C33 C34 1.382(6) . ?
C33 N2 1.415(5) . ?
C34 C35 1.386(6) . ?
C35 C36 1.382(7) . ?
C36 C37 1.389(6) . ?
C36 C39 1.469(7) . ?
C37 C38 1.387(6) . ?
C39 O3 1.200(6) . ?
C39 O4 1.338(7) . ?
C40 O4 1.448(6) . ?

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
C3 C2 C1 117.7(7) . . ?
C3 C2 C4 115.4(5) . . ?
C1 C2 C4 112.6(5) . . ?
C9 C4 C5 116.5(4) . . ?
C9 C4 C2 120.2(5) . . ?
C5 C4 C2 123.4(5) . . ?
C6 C5 C4 122.3(5) . . ?
C5 C6 C7 120.7(5) . . ?
C8 C7 C6 117.5(4) . . ?
C8 C7 C10 122.8(5) . . ?
C6 C7 C10 119.5(5) . . ?
C9 C8 C7 120.6(5) . . ?
C8 C9 C4 122.3(5) . . ?
C11 C10 N1 108.6(4) . . ?
C11 C10 C7 126.2(4) . . ?
N1 C10 C7 124.7(4) . . ?
C10 C11 C12 107.5(4) . . ?
N2 C12 C13 108.0(4) . . ?
N2 C12 C11 143.2(4) . . ?
C13 C12 C11 108.5(4) . . ?
C12 C13 N1 107.5(4) . . ?
C12 C13 C14 108.6(4) . . ?
N1 C13 C14 143.5(4) . . ?
C15 C14 C13 107.4(4) . . ?
C14 C15 N2 108.1(4) . . ?
C14 C15 C16 126.4(4) . . ?
N2 C15 C16 125.3(4) . . ?
C17 C16 C21 116.0(4) . . ?
C17 C16 C15 124.4(4) . . ?
C21 C16 C15 119.5(4) . . ?
C18 C17 C16 120.9(4) . . ?
C19 C18 C17 122.4(4) . . ?
C18 C19 C20 116.7(4) . . ?
C18 C19 C22 123.4(5) . . ?
C20 C19 C22 119.9(5) . . ?
C21 C20 C19 121.2(5) . . ?
C20 C21 C16 122.8(4) . . ?
C24 C22 C23 115.2(7) . . ?
C24 C22 C19 116.4(5) . . ?
C23 C22 C19 110.6(6) . . ?
C30 C25 C26 119.3(4) . . ?
C30 C25 N1 119.1(4) . . ?
C26 C25 N1 121.7(4) . . ?
C27 C26 C25 119.3(5) . . ?
C26 C27 C28 122.2(4) . . ?
C27 C28 C29 118.4(5) . . ?
C27 C28 C31 120.1(4) . . ?
C29 C28 C31 121.5(5) . . ?
C28 C29 C30 119.9(5) . . ?
C25 C30 C29 120.9(4) . . ?
O1 C31 O2 122.2(6) . . ?
O1 C31 C28 124.5(6) . . ?
O2 C31 C28 113.2(5) . . ?
C38 C33 C34 119.2(4) . . ?
C38 C33 N2 122.4(4) . . ?
C34 C33 N2 118.4(5) . . ?
C33 C34 C35 120.6(5) . . ?
C36 C35 C34 120.5(5) . . ?
C35 C36 C37 118.8(5) . . ?
C35 C36 C39 117.6(5) . . ?
C37 C36 C39 123.5(5) . . ?
C38 C37 C36 120.6(5) . . ?
C33 C38 C37 120.3(4) . . ?
O3 C39 O4 122.0(5) . . ?
O3 C39 C36 125.0(6) . . ?
O4 C39 C36 113.0(5) . . ?
C13 N1 C10 107.9(4) . . ?
C13 N1 C25 122.3(4) . . ?
C10 N1 C25 129.5(3) . . ?
C12 N2 C15 107.8(4) . . ?
C12 N2 C33 121.0(4) . . ?
C15 N2 C33 131.2(4) . . ?
C31 O2 C32 116.8(5) . . ?
C39 O4 C40 117.2(4) . . ?

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
C3 C2 C4 C9 134.0(8) . . . . ?
C1 C2 C4 C9 -87.0(9) . . . . ?
C3 C2 C4 C5 -46.3(9) . . . . ?
C1 C2 C4 C5 92.8(8) . . . . ?
C9 C4 C5 C6 -0.3(7) . . . . ?
C2 C4 C5 C6 179.9(5) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C5 C6 C7 C10 -175.4(4) . . . . ?
C6 C7 C8 C9 1.0(7) . . . . ?
C10 C7 C8 C9 176.5(5) . . . . ?
C7 C8 C9 C4 -2.0(8) . . . . ?
C5 C4 C9 C8 1.6(8) . . . . ?
C2 C4 C9 C8 -178.6(5) . . . . ?
C8 C7 C10 C11 -135.6(6) . . . . ?
C6 C7 C10 C11 39.8(7) . . . . ?
C8 C7 C10 N1 35.8(7) . . . . ?
C6 C7 C10 N1 -148.8(5) . . . . ?
N1 C10 C11 C12 -1.0(6) . . . . ?
C7 C10 C11 C12 171.6(5) . . . . ?
C10 C11 C12 N2 173.7(7) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
N2 C12 C13 N1 -176.4(4) . . . . ?
C11 C12 C13 N1 -1.3(6) . . . . ?
N2 C12 C13 C14 -1.9(6) . . . . ?
C11 C12 C13 C14 173.2(4) . . . . ?
C12 C13 C14 C15 2.1(6) . . . . ?
N1 C13 C14 C15 173.2(7) . . . . ?
C13 C14 C15 N2 -1.4(6) . . . . ?
C13 C14 C15 C16 174.9(5) . . . . ?
C14 C15 C16 C17 -149.4(5) . . . . ?
N2 C15 C16 C17 26.3(8) . . . . ?
C14 C15 C16 C21 26.9(8) . . . . ?
N2 C15 C16 C21 -157.4(5) . . . . ?
C21 C16 C17 C18 1.8(7) . . . . ?
C15 C16 C17 C18 178.2(5) . . . . ?
C16 C17 C18 C19 -1.6(8) . . . . ?
C17 C18 C19 C20 0.7(9) . . . . ?
C17 C18 C19 C22 -179.8(6) . . . . ?
C18 C19 C20 C21 -0.1(9) . . . . ?
C22 C19 C20 C21 -179.6(6) . . . . ?
C19 C20 C21 C16 0.4(9) . . . . ?
C17 C16 C21 C20 -1.2(8) . . . . ?
C15 C16 C21 C20 -177.9(5) . . . . ?
C18 C19 C22 C24 -26.5(11) . . . . ?
C20 C19 C22 C24 152.9(7) . . . . ?
C18 C19 C22 C23 107.4(8) . . . . ?
C20 C19 C22 C23 -73.1(9) . . . . ?
C30 C25 C26 C27 0.3(7) . . . . ?
N1 C25 C26 C27 179.3(4) . . . . ?
C25 C26 C27 C28 -0.1(8) . . . . ?
C26 C27 C28 C29 -0.3(8) . . . . ?
C26 C27 C28 C31 179.3(5) . . . . ?
C27 C28 C29 C30 0.5(8) . . . . ?
C31 C28 C29 C30 -179.1(5) . . . . ?
C26 C25 C30 C29 0.0(7) . . . . ?
N1 C25 C30 C29 -179.0(4) . . . . ?
C28 C29 C30 C25 -0.4(7) . . . . ?
C27 C28 C31 O1 0.9(9) . . . . ?
C29 C28 C31 O1 -179.4(6) . . . . ?
C27 C28 C31 O2 -176.9(5) . . . . ?
C29 C28 C31 O2 2.7(8) . . . . ?
C38 C33 C34 C35 1.8(7) . . . . ?
N2 C33 C34 C35 -177.0(4) . . . . ?
C33 C34 C35 C36 -1.6(7) . . . . ?
C34 C35 C36 C37 0.6(7) . . . . ?
C34 C35 C36 C39 177.4(4) . . . . ?
C35 C36 C37 C38 0.3(7) . . . . ?
C39 C36 C37 C38 -176.4(4) . . . . ?
C34 C33 C38 C37 -0.9(7) . . . . ?
N2 C33 C38 C37 177.8(4) . . . . ?
C36 C37 C38 C33 -0.1(7) . . . . ?
C35 C36 C39 O3 3.1(7) . . . . ?
C37 C36 C39 O3 179.7(5) . . . . ?
C35 C36 C39 O4 -177.9(4) . . . . ?
C37 C36 C39 O4 -1.2(6) . . . . ?
C12 C13 N1 C10 0.7(5) . . . . ?
C14 C13 N1 C10 -170.6(7) . . . . ?
C12 C13 N1 C25 175.7(4) . . . . ?
C14 C13 N1 C25 4.5(10) . . . . ?
C11 C10 N1 C13 0.2(6) . . . . ?
C7 C10 N1 C13 -172.5(4) . . . . ?
C11 C10 N1 C25 -174.4(5) . . . . ?
C7 C10 N1 C25 12.9(8) . . . . ?
C30 C25 N1 C13 47.4(7) . . . . ?
C26 C25 N1 C13 -131.6(5) . . . . ?
C30 C25 N1 C10 -138.7(5) . . . . ?
C26 C25 N1 C10 42.3(8) . . . . ?
C13 C12 N2 C15 1.0(5) . . . . ?
C11 C12 N2 C15 -171.3(7) . . . . ?
C13 C12 N2 C33 178.6(4) . . . . ?
C11 C12 N2 C33 6.2(10) . . . . ?
C14 C15 N2 C12 0.3(6) . . . . ?
C16 C15 N2 C12 -176.1(5) . . . . ?
C14 C15 N2 C33 -177.0(5) . . . . ?
C16 C15 N2 C33 6.7(8) . . . . ?
C38 C33 N2 C12 -128.2(5) . . . . ?
C34 C33 N2 C12 50.5(6) . . . . ?
C38 C33 N2 C15 48.7(7) . . . . ?
C34 C33 N2 C15 -132.6(5) . . . . ?
O1 C31 O2 C32 0.5(10) . . . . ?
C28 C31 O2 C32 178.4(5) . . . . ?
O3 C39 O4 C40 -4.5(7) . . . . ?
C36 C39 O4 C40 176.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_bwn16151a
_database_code_depnum_ccdc_archive 'CCDC 1544605'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_audit_creation_date             2016-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C40 H38 N2 O4'
_chemical_formula_sum            'C40 H38 N2 O4'
_chemical_formula_weight         610.72
_chemical_melting_point          ?
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6456(11)
_cell_length_b                   12.856(3)
_cell_length_c                   22.586(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.79(3)
_cell_angle_gamma                90.00
_cell_volume                     1627.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.8160
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5486
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.41
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.7665
	          2theta: -20.1728
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3702
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0200
_diffrn_orient_matrix_UB_12      0.1405
_diffrn_orient_matrix_UB_13      0.1081
_diffrn_orient_matrix_UB_21      0.0718
_diffrn_orient_matrix_UB_22      -0.0240
_diffrn_orient_matrix_UB_23      0.0179
_diffrn_orient_matrix_UB_31      0.0169
_diffrn_orient_matrix_UB_32      0.0278
_diffrn_orient_matrix_UB_33      -0.0305
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2088
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.1004
_refine_ls_restrained_S_all      1.174
_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)+(0.0110P)²+3.0320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1586
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_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 0.8517(5) 0.6106(2) 0.24713(12) 0.0287(7) Uani 1 d . . .
O2 O 0.5445(5) 0.6249(3) 0.30095(13) 0.0392(9) Uani 1 d . . .
N1 N 0.2008(5) 0.8974(2) 0.00837(13) 0.0188(8) Uani 1 d . . .
C1 C -0.0031(7) 1.0185(3) -0.07746(16) 0.0177(9) Uani 1 d . . .
H1 H 0.0538 0.9984 -0.1137 0.021 Uiso 1 calc . . R
C2 C 0.0587(7) 0.9750(3) -0.02076(16) 0.0183(9) Uani 1 d . . .
C3 C 0.3272(7) 0.8220(3) -0.02224(16) 0.0178(9) Uani 1 d . . .
C4 C 0.2618(7) 0.7179(3) -0.02189(18) 0.0248(10) Uani 1 d . . .
H4 H 0.1355 0.6960 -0.0005 0.030 Uiso 1 calc . . R
C5 C 0.3828(7) 0.6462(3) -0.05306(18) 0.0283(10) Uani 1 d . . .
H5 H 0.3386 0.5749 -0.0527 0.034 Uiso 1 calc . . R
C6 C 0.5681(7) 0.6768(3) -0.08491(17) 0.0217(9) Uani 1 d . . .
C7 C 0.6285(7) 0.7824(3) -0.08458(18) 0.0258(10) Uani 1 d . . .
H7 H 0.7525 0.8051 -0.1065 0.031 Uiso 1 calc . . R
C8 C 0.5108(7) 0.8542(3) -0.05294(17) 0.0232(10) Uani 1 d . . .
H8 H 0.5565 0.9253 -0.0524 0.028 Uiso 1 calc . . R
C9 C 0.6895(8) 0.6012(3) -0.12357(19) 0.0304(11) Uani 1 d . . .
H9 H 0.8319 0.6368 -0.1367 0.037 Uiso 1 calc . . R
C10 C 0.5174(9) 0.5746(4) -0.17941(19) 0.0421(13) Uani 1 d . . .
H10A H 0.3778 0.5383 -0.1676 0.063 Uiso 1 calc . . GR
H10B H 0.5986 0.5298 -0.2057 0.063 Uiso 1 calc . . GR
H10C H 0.4661 0.6389 -0.2005 0.063 Uiso 1 calc . . GR
C11 C 0.7749(9) 0.5013(4) -0.0903(2) 0.0442(13) Uani 1 d . . .
H11A H 0.8807 0.5194 -0.0542 0.066 Uiso 1 calc . . GR
H11B H 0.8615 0.4579 -0.1162 0.066 Uiso 1 calc . . GR
H11C H 0.6368 0.4628 -0.0793 0.066 Uiso 1 calc . . GR
C12 C 0.1661(7) 0.9023(3) 0.06927(16) 0.0188(9) Uani 1 d . . .
C13 C 0.2961(7) 0.8369(3) 0.11563(17) 0.0192(9) Uani 1 d . . .
C14 C 0.5172(7) 0.7904(3) 0.11041(17) 0.0221(9) Uani 1 d . . .
H14 H 0.5912 0.8009 0.0752 0.027 Uiso 1 calc . . R
C15 C 0.6287(7) 0.7294(3) 0.15580(17) 0.0217(9) Uani 1 d . . .
H15 H 0.7770 0.6974 0.1510 0.026 Uiso 1 calc . . R
C16 C 0.5274(7) 0.7141(3) 0.20832(17) 0.0209(9) Uani 1 d . . .
C17 C 0.3105(7) 0.7624(3) 0.21452(17) 0.0247(10) Uani 1 d . . .
H17 H 0.2407 0.7539 0.2505 0.030 Uiso 1 calc . . R
C18 C 0.1960(7) 0.8224(3) 0.16916(17) 0.0225(9) Uani 1 d . . .
H18 H 0.0478 0.8542 0.1742 0.027 Uiso 1 calc . . R
C19 C 0.6382(7) 0.6465(3) 0.25725(18) 0.0253(10) Uani 1 d . . .
C20 C 0.9620(8) 0.5354(3) 0.28981(19) 0.0350(12) Uani 1 d . . .
H20A H 0.8877 0.4671 0.2818 0.052 Uiso 1 calc . . GR
H20B H 0.9399 0.5576 0.3303 0.052 Uiso 1 calc . . GR
H20C H 1.1329 0.5307 0.2861 0.052 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 C19 1.336(5) . ?
O1 C20 1.453(5) . ?
O2 C19 1.206(5) . ?
N1 C2 1.395(5) . ?
N1 C3 1.429(5) . ?
N1 C12 1.414(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(5) . ?
C1 C12 1.400(5) 3_575 ?
C2 C2 1.371(7) 3_575 ?
C3 C4 1.389(5) . ?
C3 C8 1.377(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 C7 1.398(5) . ?
C6 C9 1.523(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(5) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.537(6) . ?
C9 C11 1.537(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C1 1.400(5) 3_575 ?
C12 C13 1.470(5) . ?
C13 C14 1.401(5) . ?
C13 C18 1.406(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(5) . ?
C16 C17 1.395(6) . ?
C16 C19 1.484(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C19 O1 C20 116.2(3) . . ?
C2 N1 C3 123.3(3) . . ?
C2 N1 C12 106.8(3) . . ?
C12 N1 C3 129.5(3) . . ?
C2 C1 H1 127.3 . . ?
C12 C1 H1 127.3 3_575 . ?
C12 C1 C2 105.4(3) 3_575 . ?
N1 C2 C1 141.4(3) . . ?
C2 C2 N1 108.1(4) 3_575 . ?
C2 C2 C1 110.5(4) 3_575 . ?
C4 C3 N1 120.2(4) . . ?
C8 C3 N1 119.2(3) . . ?
C8 C3 C4 120.6(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 118.0(4) . . ?
C5 C6 C9 122.1(4) . . ?
C7 C6 C9 119.7(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(4) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 119.7(4) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C6 C9 H9 108.1 . . ?
C6 C9 C10 109.2(4) . . ?
C6 C9 C11 112.9(4) . . ?
C10 C9 H9 108.1 . . ?
C10 C9 C11 110.3(4) . . ?
C11 C9 H9 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 123.5(3) . . ?
C1 C12 N1 109.3(3) 3_575 . ?
C1 C12 C13 127.1(3) 3_575 . ?
C14 C13 C12 124.0(4) . . ?
C14 C13 C18 117.9(4) . . ?
C18 C13 C12 118.1(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.5(4) . . ?
C15 C16 C19 122.6(4) . . ?
C17 C16 C19 118.9(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(4) . . ?
C17 C18 H18 119.6 . . ?
O1 C19 C16 112.6(4) . . ?
O2 C19 O1 123.6(4) . . ?
O2 C19 C16 123.8(4) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N1 C3 C4 C5 178.5(3) . . . . ?
N1 C3 C8 C7 -177.6(4) . . . . ?
N1 C12 C13 C14 22.9(6) . . . . ?
N1 C12 C13 C18 -159.0(4) . . . . ?
C1 C12 C13 C14 -153.3(4) 3_575 . . . ?
C1 C12 C13 C18 24.9(6) 3_575 . . . ?
C2 N1 C3 C4 -112.6(4) . . . . ?
C2 N1 C3 C8 66.2(5) . . . . ?
C2 N1 C12 C1 0.4(4) . . . 3_575 ?
C2 N1 C12 C13 -176.3(3) . . . . ?
C3 N1 C2 C1 -7.6(8) . . . . ?
C3 N1 C2 C2 172.5(4) . . . 3_575 ?
C3 N1 C12 C1 -171.7(3) . . . 3_575 ?
C3 N1 C12 C13 11.6(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C3 C8 C7 1.1(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C4 C5 C6 C9 -174.8(4) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C5 C6 C9 C10 71.5(5) . . . . ?
C5 C6 C9 C11 -51.6(5) . . . . ?
C6 C7 C8 C3 -1.5(6) . . . . ?
C7 C6 C9 C10 -103.2(4) . . . . ?
C7 C6 C9 C11 133.7(4) . . . . ?
C8 C3 C4 C5 -0.3(6) . . . . ?
C9 C6 C7 C8 175.8(4) . . . . ?
C12 N1 C2 C1 179.6(5) . . . . ?
C12 N1 C2 C2 -0.2(5) . . . 3_575 ?
C12 N1 C3 C4 58.4(6) . . . . ?
C12 N1 C3 C8 -122.8(4) . . . . ?
C12 C1 C2 N1 179.8(5) 3_575 . . . ?
C12 C1 C2 C2 -0.4(5) 3_575 . . 3_575 ?
C12 C13 C14 C15 -179.7(4) . . . . ?
C12 C13 C18 C17 -179.5(4) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C14 C13 C18 C17 -1.2(6) . . . . ?
C14 C15 C16 C17 -0.5(6) . . . . ?
C14 C15 C16 C19 178.1(4) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C15 C16 C19 O1 5.4(6) . . . . ?
C15 C16 C19 O2 -173.5(4) . . . . ?
C16 C17 C18 C13 -0.5(6) . . . . ?
C17 C16 C19 O1 -176.0(4) . . . . ?
C17 C16 C19 O2 5.0(6) . . . . ?
C18 C13 C14 C15 2.1(6) . . . . ?
C19 C16 C17 C18 -177.2(4) . . . . ?
C20 O1 C19 O2 5.0(6) . . . . ?
C20 O1 C19 C16 -173.9(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_bwn16128
_database_code_depnum_ccdc_archive 'CCDC 1544599'
_audit_update_record             
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 H7 N O), C34 H18 N6'
_chemical_formula_sum            'C40 H32 N8 O2'
_chemical_formula_weight         656.74
_chemical_melting_point          ?
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                   11.720(2)
_cell_length_b                   6.2246(12)
_cell_length_c                   23.409(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.65(3)
_cell_angle_gamma                90.00
_cell_volume                     1683.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.0993
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7546
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9581
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.8516
	          2theta: -20.1738
scan:
	Number of images: 270
	           Slice: -110.0000 - 25.0000
	     Image width: 0.5000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.8516
	          2theta: -20.1738
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4194
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0472
_diffrn_orient_matrix_UB_12      0.0636
_diffrn_orient_matrix_UB_13      -0.0349
_diffrn_orient_matrix_UB_21      0.0237
_diffrn_orient_matrix_UB_22      -0.0625
_diffrn_orient_matrix_UB_23      -0.1461
_diffrn_orient_matrix_UB_31      -0.0392
_diffrn_orient_matrix_UB_32      -0.0184
_diffrn_orient_matrix_UB_33      0.0015
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2603
_reflns_number_total             2947
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.272
_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)+(0.0680P)²+0.7840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1715
_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:
 C18(H18), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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 0.3671(2) 0.0985(5) 0.03714(11) 0.0631(8) Uani 1 d . . .
N4 N 0.4930(2) -0.1542(5) 0.07940(12) 0.0454(7) Uani 1 d . . .
C18 C 0.4585(3) 0.0457(6) 0.06695(14) 0.0468(9) Uani 1 d . . .
H18 H 0.5094 0.1577 0.0826 0.056 Uiso 1 calc . . R
C19 C 0.4236(4) -0.3358(7) 0.05610(19) 0.0713(12) Uani 1 d . . .
H19A H 0.3522 -0.2844 0.0321 0.107 Uiso 1 calc . . GR
H19B H 0.4041 -0.4229 0.0880 0.107 Uiso 1 calc . . GR
H19C H 0.4672 -0.4233 0.0324 0.107 Uiso 1 calc . . GR
C20 C 0.6050(3) -0.2009(8) 0.1138(2) 0.0782(14) Uani 1 d . . .
H20A H 0.6533 -0.2759 0.0898 0.117 Uiso 1 calc . . GR
H20B H 0.5948 -0.2922 0.1467 0.117 Uiso 1 calc . . GR
H20C H 0.6428 -0.0664 0.1282 0.117 Uiso 1 calc . . GR
N1 N -0.1928(2) 1.5718(4) 0.22287(11) 0.0410(7) Uani 1 d . . .
N2 N 0.04871(17) 0.6256(3) 0.06512(9) 0.0215(5) Uani 1 d . . .
N3 N 0.4832(2) 0.7340(4) 0.29431(12) 0.0451(7) Uani 1 d . . .
C1 C -0.1716(2) 1.4330(4) 0.19329(12) 0.0296(6) Uani 1 d . . .
C2 C -0.1428(2) 1.2618(4) 0.15731(12) 0.0259(6) Uani 1 d . . .
C3 C -0.1675(2) 1.2786(4) 0.09701(11) 0.0279(6) Uani 1 d . . .
H3 H -0.2063 1.4020 0.0795 0.034 Uiso 1 calc . . R
C4 C -0.1357(2) 1.1160(4) 0.06296(12) 0.0262(6) Uani 1 d . . .
H4 H -0.1527 1.1292 0.0220 0.031 Uiso 1 calc . . R
C5 C -0.0786(2) 0.9313(4) 0.08747(11) 0.0218(6) Uani 1 d . . .
C6 C -0.0564(2) 0.9159(4) 0.14837(11) 0.0270(6) Uani 1 d . . .
H6 H -0.0190 0.7916 0.1661 0.032 Uiso 1 calc . . R
C7 C -0.0881(2) 1.0782(4) 0.18270(12) 0.0290(6) Uani 1 d . . .
H7 H -0.0726 1.0648 0.2237 0.035 Uiso 1 calc . . R
C8 C -0.0479(2) 0.7617(4) 0.04980(11) 0.0225(6) Uani 1 d . . .
C9 C 0.0477(2) 0.4786(4) 0.02088(10) 0.0221(6) Uani 1 d . . .
C10 C 0.1092(2) 0.3018(4) 0.00329(11) 0.0226(6) Uani 1 d . . .
H10 H 0.1782 0.2396 0.0237 0.027 Uiso 1 calc . . R
C11 C 0.1416(2) 0.6495(4) 0.11298(11) 0.0210(6) Uani 1 d . . .
C12 C 0.1725(2) 0.4748(4) 0.14918(11) 0.0255(6) Uani 1 d . . .
H12 H 0.1323 0.3423 0.1423 0.031 Uiso 1 calc . . R
C13 C 0.2626(2) 0.4958(4) 0.19551(12) 0.0276(6) Uani 1 d . . .
H13 H 0.2843 0.3780 0.2208 0.033 Uiso 1 calc . . R
C14 C 0.3211(2) 0.6907(4) 0.20466(11) 0.0252(6) Uani 1 d . . .
C15 C 0.2910(2) 0.8644(4) 0.16794(12) 0.0262(6) Uani 1 d . . .
H15 H 0.3316 0.9966 0.1745 0.031 Uiso 1 calc . . R
C16 C 0.2010(2) 0.8429(4) 0.12159(11) 0.0242(6) Uani 1 d . . .
H16 H 0.1802 0.9599 0.0959 0.029 Uiso 1 calc . . R
C17 C 0.4121(2) 0.7150(5) 0.25436(13) 0.0324(7) 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 C18 1.222(4) . ?
N4 C18 1.325(4) . ?
N4 C19 1.446(5) . ?
N4 C20 1.450(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 C1 1.160(4) . ?
N2 C8 1.411(3) . ?
N2 C9 1.381(3) . ?
N2 C11 1.433(3) . ?
N3 C17 1.149(4) . ?
C1 C2 1.433(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(4) . ?
C5 C6 1.409(4) . ?
C5 C8 1.459(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C10 1.385(3) 3_565 ?
C9 C9 1.382(5) 3_565 ?
C9 C10 1.414(3) . ?
C10 C8 1.385(3) 3_565 ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 C16 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 C15 1.390(4) . ?
C14 C17 1.449(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(4) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N4 C19 121.3(3) . . ?
C18 N4 C20 121.7(3) . . ?
C19 N4 C20 116.9(3) . . ?
O1 C18 N4 125.8(4) . . ?
O1 C18 H18 117.1 . . ?
N4 C18 H18 117.1 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N2 C11 127.5(2) . . ?
C9 N2 C8 107.55(19) . . ?
C9 N2 C11 124.4(2) . . ?
N1 C1 C2 178.8(3) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 119.7(2) . . ?
C7 C2 C3 119.7(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 C8 119.6(2) . . ?
C6 C5 C8 122.7(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
N2 C8 C5 123.3(2) . . ?
C10 C8 N2 109.3(2) 3_565 . ?
C10 C8 C5 127.3(2) 3_565 . ?
N2 C9 C9 107.9(3) . 3_565 ?
N2 C9 C10 142.5(2) . . ?
C9 C9 C10 109.6(3) 3_565 . ?
C8 C10 C9 105.7(2) 3_565 . ?
C8 C10 H10 127.1 3_565 . ?
C9 C10 H10 127.1 . . ?
C12 C11 N2 118.8(2) . . ?
C16 C11 N2 120.0(2) . . ?
C16 C11 C12 121.1(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C17 119.5(2) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 C17 119.5(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
N3 C17 C14 179.0(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
C19 N4 C18 O1 2.1(5) . . . . ?
C20 N4 C18 O1 178.0(3) . . . . ?
N1 C1 C2 C3 -122(14) . . . . ?
N1 C1 C2 C7 57(14) . . . . ?
N2 C9 C10 C8 179.7(3) . . . 3_565 ?
N2 C11 C12 C13 179.7(2) . . . . ?
N2 C11 C16 C15 -179.8(2) . . . . ?
C1 C2 C3 C4 177.7(2) . . . . ?
C1 C2 C7 C6 -177.7(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C8 179.2(2) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C4 C5 C8 N2 150.3(2) . . . . ?
C4 C5 C8 C10 -34.2(4) . . . 3_565 ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C6 C5 C8 N2 -31.6(4) . . . . ?
C6 C5 C8 C10 144.0(3) . . . 3_565 ?
C7 C2 C3 C4 -1.4(4) . . . . ?
C8 N2 C9 C9 -0.3(3) . . . 3_565 ?
C8 N2 C9 C10 179.5(3) . . . . ?
C8 N2 C11 C12 130.1(3) . . . . ?
C8 N2 C11 C16 -51.7(3) . . . . ?
C8 C5 C6 C7 -179.1(2) . . . . ?
C9 N2 C8 C5 176.9(2) . . . . ?
C9 N2 C8 C10 0.6(3) . . . 3_565 ?
C9 N2 C11 C12 -59.6(3) . . . . ?
C9 N2 C11 C16 118.6(3) . . . . ?
C9 C9 C10 C8 -0.5(3) 3_565 . . 3_565 ?
C11 N2 C8 C5 -11.5(4) . . . . ?
C11 N2 C8 C10 172.2(2) . . . 3_565 ?
C11 N2 C9 C9 -172.2(2) . . . 3_565 ?
C11 N2 C9 C10 7.6(5) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C11 C16 C15 -1.6(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C12 C13 C14 C17 177.6(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C14 C17 N3 -66(18) . . . . ?
C14 C15 C16 C11 0.8(4) . . . . ?
C15 C14 C17 N3 112(18) . . . . ?
C16 C11 C12 C13 1.5(4) . . . . ?
C17 C14 C15 C16 -177.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
