# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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 1823469'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H14 N4 O2'
_chemical_formula_weight         450.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.0052(2)
_cell_length_b                   15.6076(4)
_cell_length_c                   14.6006(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.275(3)
_cell_angle_gamma                90.00
_cell_volume                     1140.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4788
_cell_measurement_theta_min      5.6610
_cell_measurement_theta_max      71.6150

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8101
_exptl_absorpt_correction_T_max  0.8470
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0356
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10417
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.43
_diffrn_reflns_theta_max         66.04
_reflns_number_total             3890
_reflns_number_gt                3658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0531P)²+0.0599P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0158(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         3890
_refine_ls_number_parameters     321
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
N1 N 1.1511(5) 0.29625(15) 0.77261(16) 0.0943(6) Uani 1 1 d . . .
N2 N 0.7244(6) 0.33164(16) 0.51799(15) 0.1184(9) Uani 1 1 d . . .
N3 N -0.630(2) 0.6120(5) 1.2161(8) 0.114(3) Uani 0.660(17) 1 d P A 1
N3' N -0.728(4) 0.6168(11) 1.1785(12) 0.114(3) Uani 0.340(17) 1 d P A 2
N4 N -0.6691(5) 0.85394(16) 1.06275(16) 0.1008(7) Uani 1 1 d . A .
O1 O 0.3911(2) 0.55481(8) 0.84078(7) 0.0540(3) Uani 1 1 d . . .
O2 O -0.0592(2) 0.56250(7) 0.88391(8) 0.0553(3) Uani 1 1 d . . .
C1 C 0.1415(3) 0.61899(11) 0.72020(11) 0.0511(4) Uani 1 1 d . . .
C2 C 0.3181(3) 0.55715(11) 0.74894(11) 0.0489(4) Uani 1 1 d . . .
C3 C 0.4413(3) 0.49877(10) 0.68806(11) 0.0502(4) Uani 1 1 d . . .
C4 C 0.3644(4) 0.50336(12) 0.59708(12) 0.0597(4) Uani 1 1 d . . .
H4 H 0.4446 0.4669 0.5555 0.072 Uiso 1 1 calc R . .
C5 C 0.1691(4) 0.56116(12) 0.56486(12) 0.0598(4) Uani 1 1 d . . .
C6 C 0.0518(4) 0.61986(11) 0.62631(12) 0.0563(4) Uani 1 1 d . . .
C7 C -0.1510(4) 0.67460(13) 0.59230(15) 0.0678(5) Uani 1 1 d . . .
H7 H -0.2338 0.7126 0.6317 0.081 Uiso 1 1 calc R . .
C8 C -0.2268(6) 0.67226(14) 0.50225(17) 0.0837(7) Uani 1 1 d . . .
H8 H -0.3618 0.7086 0.4810 0.100 Uiso 1 1 calc R . .
C9 C -0.1060(6) 0.61655(17) 0.44143(16) 0.0923(8) Uani 1 1 d . . .
H9 H -0.1572 0.6168 0.3798 0.111 Uiso 1 1 calc R . .
C10 C 0.0845(5) 0.56239(16) 0.47170(14) 0.0814(6) Uani 1 1 d . . .
H10 H 0.1626 0.5249 0.4306 0.098 Uiso 1 1 calc R . .
C11 C 0.6451(4) 0.44187(10) 0.72567(12) 0.0516(4) Uani 1 1 d . . .
H11 H 0.6847 0.4493 0.7877 0.062 Uiso 1 1 calc R . .
C12 C 0.7852(4) 0.37999(11) 0.68438(12) 0.0527(4) Uani 1 1 d . . .
C13 C 0.9870(4) 0.33311(12) 0.73458(14) 0.0629(5) Uani 1 1 d . . .
C14 C 0.7508(5) 0.35411(13) 0.59138(15) 0.0724(5) Uani 1 1 d . . .
C15 C 0.0460(4) 0.68106(11) 0.78958(13) 0.0545(4) Uani 1 1 d . . .
C16 C -0.0584(4) 0.64996(11) 0.86864(13) 0.0537(4) Uani 1 1 d . . .
C17 C -0.1807(4) 0.70384(12) 0.93444(14) 0.0615(5) Uani 1 1 d . . .
C18 C -0.1707(5) 0.79073(13) 0.91943(16) 0.0762(6) Uani 1 1 d . . .
H18 H -0.2525 0.8271 0.9607 0.091 Uiso 1 1 calc R . .
C19 C -0.0419(5) 0.82641(13) 0.84442(16) 0.0747(6) Uani 1 1 d . . .
C20 C 0.0717(4) 0.77229(11) 0.77805(14) 0.0615(5) Uani 1 1 d . . .
C21 C 0.2119(5) 0.80970(13) 0.70619(15) 0.0724(6) Uani 1 1 d . . .
H21 H 0.2878 0.7750 0.6620 0.087 Uiso 1 1 calc R . .
C22 C 0.2380(7) 0.89711(15) 0.70049(18) 0.0937(8) Uani 1 1 d . . .
H22 H 0.3348 0.9210 0.6532 0.112 Uiso 1 1 calc R . .
C23 C 0.1210(8) 0.95014(16) 0.7648(2) 0.1130(11) Uani 1 1 d . . .
H23 H 0.1378 1.0093 0.7599 0.136 Uiso 1 1 calc R . .
C24 C -0.0160(7) 0.91638(15) 0.8340(2) 0.1039(9) Uani 1 1 d . . .
H24 H -0.0955 0.9526 0.8760 0.125 Uiso 1 1 calc R . .
C25 C -0.3067(4) 0.66538(12) 1.01223(15) 0.0682(5) Uani 1 1 d . . .
H25 H -0.2618 0.6085 1.0237 0.082 Uiso 1 1 calc R . .
C26 C -0.4808(5) 0.70044(13) 1.07073(15) 0.0701(5) Uani 1 1 d . A .
C27 C -0.5781(7) 0.65152(16) 1.1459(2) 0.0992(9) Uani 1 1 d . . .
C28 C -0.5828(5) 0.78669(16) 1.06482(15) 0.0746(6) Uani 1 1 d . . .
C29 C 0.1919(4) 0.52376(11) 0.89899(12) 0.0559(4) Uani 1 1 d . . .
H29A H 0.1740 0.4624 0.8901 0.067 Uiso 1 1 calc R . .
H29B H 0.2486 0.5334 0.9621 0.067 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 C13 1.138(3) . ?
N2 C14 1.132(3) . ?
N3 C27 1.229(10) . ?
N3' C27 1.046(17) . ?
N4 C28 1.135(3) . ?
O1 C2 1.3824(19) . ?
O1 C29 1.410(2) . ?
O2 C16 1.383(2) . ?
O2 C29 1.407(2) . ?
C1 C2 1.368(2) . ?
C1 C6 1.433(2) . ?
C1 C15 1.488(2) . ?
C2 C3 1.423(2) . ?
C3 C4 1.377(2) . ?
C3 C11 1.451(2) . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.416(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.361(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.342(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.344(2) . ?
C11 H11 0.9300 . ?
C12 C14 1.423(3) . ?
C12 C13 1.435(3) . ?
C15 C16 1.367(3) . ?
C15 C20 1.440(2) . ?
C16 C17 1.425(2) . ?
C17 C18 1.375(3) . ?
C17 C25 1.442(3) . ?
C18 C19 1.399(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.414(3) . ?
C19 C24 1.419(3) . ?
C20 C21 1.402(3) . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.341(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.349(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.432(4) . ?
C26 C28 1.442(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?

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 O1 C29 114.76(12) . . ?
C16 O2 C29 116.34(14) . . ?
C2 C1 C6 119.12(14) . . ?
C2 C1 C15 117.75(15) . . ?
C6 C1 C15 123.11(16) . . ?
C1 C2 O1 118.10(14) . . ?
C1 C2 C3 123.09(14) . . ?
O1 C2 C3 118.71(14) . . ?
C4 C3 C2 116.99(15) . . ?
C4 C3 C11 125.17(15) . . ?
C2 C3 C11 117.79(14) . . ?
C3 C4 C5 122.31(16) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C10 121.45(17) . . ?
C4 C5 C6 119.86(15) . . ?
C10 C5 C6 118.68(18) . . ?
C7 C6 C5 118.28(16) . . ?
C7 C6 C1 123.43(17) . . ?
C5 C6 C1 118.27(15) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C12 C11 C3 129.74(16) . . ?
C12 C11 H11 115.1 . . ?
C3 C11 H11 115.1 . . ?
C11 C12 C14 125.36(18) . . ?
C11 C12 C13 120.36(16) . . ?
C14 C12 C13 114.28(16) . . ?
N1 C13 C12 178.3(2) . . ?
N2 C14 C12 178.4(2) . . ?
C16 C15 C20 119.13(16) . . ?
C16 C15 C1 118.58(15) . . ?
C20 C15 C1 122.22(17) . . ?
C15 C16 O2 119.27(15) . . ?
C15 C16 C17 122.54(16) . . ?
O2 C16 C17 118.10(16) . . ?
C18 C17 C16 117.18(18) . . ?
C18 C17 C25 123.66(17) . . ?
C16 C17 C25 119.16(16) . . ?
C17 C18 C19 122.45(18) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 119.87(18) . . ?
C18 C19 C24 121.5(2) . . ?
C20 C19 C24 118.6(2) . . ?
C21 C20 C19 118.65(17) . . ?
C21 C20 C15 123.14(17) . . ?
C19 C20 C15 118.17(18) . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 121.3(2) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C26 C25 C17 129.0(2) . . ?
C26 C25 H25 115.5 . . ?
C17 C25 H25 115.5 . . ?
C25 C26 C27 120.3(2) . . ?
C25 C26 C28 125.0(2) . . ?
C27 C26 C28 114.69(19) . . ?
N3' C27 N3 36.4(10) . . ?
N3' C27 C26 152.0(12) . . ?
N3 C27 C26 171.6(7) . . ?
N4 C28 C26 177.5(3) . . ?
O2 C29 O1 113.50(14) . . ?
O2 C29 H29A 108.9 . . ?
O1 C29 H29A 108.9 . . ?
O2 C29 H29B 108.9 . . ?
O1 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?

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 O1 -176.67(14) . . . . ?
C15 C1 C2 O1 1.7(2) . . . . ?
C6 C1 C2 C3 7.1(2) . . . . ?
C15 C1 C2 C3 -174.52(16) . . . . ?
C29 O1 C2 C1 73.28(19) . . . . ?
C29 O1 C2 C3 -110.36(17) . . . . ?
C1 C2 C3 C4 -3.5(2) . . . . ?
O1 C2 C3 C4 -179.69(15) . . . . ?
C1 C2 C3 C11 173.91(16) . . . . ?
O1 C2 C3 C11 -2.3(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C11 C3 C4 C5 -178.71(17) . . . . ?
C3 C4 C5 C10 -177.3(2) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
C4 C5 C6 C7 -177.52(18) . . . . ?
C10 C5 C6 C7 2.3(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C10 C5 C6 C1 -179.10(18) . . . . ?
C2 C1 C6 C7 172.75(17) . . . . ?
C15 C1 C6 C7 -5.5(3) . . . . ?
C2 C1 C6 C5 -5.7(2) . . . . ?
C15 C1 C6 C5 176.03(16) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C1 C6 C7 C8 179.9(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C8 C9 C10 C5 -0.8(4) . . . . ?
C4 C5 C10 C9 178.7(2) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C4 C3 C11 C12 -4.9(3) . . . . ?
C2 C3 C11 C12 177.94(17) . . . . ?
C3 C11 C12 C14 -3.1(3) . . . . ?
C3 C11 C12 C13 177.56(17) . . . . ?
C11 C12 C13 N1 -133(8) . . . . ?
C14 C12 C13 N1 48(8) . . . . ?
C11 C12 C14 N2 -142(11) . . . . ?
C13 C12 C14 N2 38(11) . . . . ?
C2 C1 C15 C16 -52.3(2) . . . . ?
C6 C1 C15 C16 126.0(2) . . . . ?
C2 C1 C15 C20 124.7(2) . . . . ?
C6 C1 C15 C20 -57.0(2) . . . . ?
C20 C15 C16 O2 -173.65(16) . . . . ?
C1 C15 C16 O2 3.4(3) . . . . ?
C20 C15 C16 C17 9.8(3) . . . . ?
C1 C15 C16 C17 -173.13(17) . . . . ?
C29 O2 C16 C15 68.3(2) . . . . ?
C29 O2 C16 C17 -115.03(18) . . . . ?
C15 C16 C17 C18 -5.4(3) . . . . ?
O2 C16 C17 C18 178.05(18) . . . . ?
C15 C16 C17 C25 174.66(19) . . . . ?
O2 C16 C17 C25 -1.9(3) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C25 C17 C18 C19 178.5(2) . . . . ?
C17 C18 C19 C20 3.4(4) . . . . ?
C17 C18 C19 C24 -175.1(3) . . . . ?
C18 C19 C20 C21 -176.7(2) . . . . ?
C24 C19 C20 C21 1.8(4) . . . . ?
C18 C19 C20 C15 1.1(3) . . . . ?
C24 C19 C20 C15 179.6(2) . . . . ?
C16 C15 C20 C21 170.16(19) . . . . ?
C1 C15 C20 C21 -6.8(3) . . . . ?
C16 C15 C20 C19 -7.5(3) . . . . ?
C1 C15 C20 C19 175.59(19) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C15 C20 C21 C22 -177.6(2) . . . . ?
C20 C21 C22 C23 -1.4(4) . . . . ?
C21 C22 C23 C24 0.9(6) . . . . ?
C22 C23 C24 C19 1.0(6) . . . . ?
C18 C19 C24 C23 176.1(3) . . . . ?
C20 C19 C24 C23 -2.4(5) . . . . ?
C18 C17 C25 C26 16.1(4) . . . . ?
C16 C17 C25 C26 -164.0(2) . . . . ?
C17 C25 C26 C27 -178.3(2) . . . . ?
C17 C25 C26 C28 1.5(4) . . . . ?
C25 C26 C27 N3' -106(2) . . . . ?
C28 C26 C27 N3' 74(2) . . . . ?
C25 C26 C27 N3 79(3) . . . . ?
C28 C26 C27 N3 -101(3) . . . . ?
C25 C26 C28 N4 175(6) . . . . ?
C27 C26 C28 N4 -5(6) . . . . ?
C16 O2 C29 O1 -41.28(19) . . . . ?
C2 O1 C29 O2 -49.07(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.023
####################################################################### 
# 
# 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 1823470'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 N4 O2'
_chemical_formula_weight         464.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   25.4902(8)
_cell_length_b                   8.4676(3)
_cell_length_c                   16.9657(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.889(2)
_cell_angle_gamma                90.00
_cell_volume                     3538.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8315
_cell_measurement_theta_min      3.5770
_cell_measurement_theta_max      71.7750

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7588
_exptl_absorpt_correction_T_max  0.7728
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16635
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.01
_diffrn_reflns_theta_max         66.05
_reflns_number_total             5166
_reflns_number_gt                4833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0525P)²+0.5553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00090(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(19)
_refine_ls_number_reflns         5166
_refine_ls_number_parameters     488
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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
N1 N 0.54425(11) 0.7227(3) 0.23921(13) 0.1021(8) Uani 1 1 d . . .
N2 N 0.50692(9) 0.4021(4) 0.40676(15) 0.1102(10) Uani 1 1 d . . .
N3 N 1.04138(9) 0.5919(5) 0.79639(17) 0.1466(15) Uani 1 1 d . . .
N4 N 1.05764(9) 0.3778(5) 0.57454(15) 0.1227(12) Uani 1 1 d . . .
N5 N 0.72190(9) 0.6106(4) 1.00784(15) 0.1026(8) Uani 1 1 d . . .
N6 N 0.64776(11) 0.8370(5) 0.7744(2) 0.1366(13) Uani 1 1 d . . .
O1 O 0.74242(5) 0.65979(16) 0.48009(7) 0.0515(3) Uani 1 1 d . . .
O2 O 0.83325(5) 0.44950(16) 0.54682(7) 0.0511(3) Uani 1 1 d . . .
O3 O 0.50384(5) 0.52062(17) 0.91777(7) 0.0568(3) Uani 1 1 d . . .
C1 C 0.74480(6) 0.5474(2) 0.60917(10) 0.0439(4) Uani 1 1 d . . .
C2 C 0.71688(7) 0.5824(2) 0.53099(10) 0.0447(4) Uani 1 1 d . . .
C3 C 0.66009(7) 0.5466(2) 0.50072(10) 0.0488(4) Uani 1 1 d . . .
C4 C 0.63483(7) 0.4664(3) 0.55069(11) 0.0541(5) Uani 1 1 d . . .
H4 H 0.5979 0.4450 0.5323 0.065 Uiso 1 1 calc R . .
C5 C 0.66286(7) 0.4158(2) 0.62859(11) 0.0491(4) Uani 1 1 d . . .
C6 C 0.71872(7) 0.4562(2) 0.65924(10) 0.0463(4) Uani 1 1 d . . .
C7 C 0.74587(7) 0.3983(3) 0.73693(11) 0.0567(5) Uani 1 1 d . . .
H7 H 0.7822 0.4242 0.7588 0.068 Uiso 1 1 calc R . .
C8 C 0.72008(8) 0.3054(3) 0.78040(12) 0.0653(6) Uani 1 1 d . . .
H8 H 0.7392 0.2673 0.8310 0.078 Uiso 1 1 calc R . .
C9 C 0.66522(8) 0.2659(3) 0.75048(13) 0.0671(6) Uani 1 1 d . . .
H9 H 0.6480 0.2023 0.7809 0.081 Uiso 1 1 calc R . .
C10 C 0.63741(8) 0.3214(3) 0.67660(12) 0.0616(5) Uani 1 1 d . . .
H10 H 0.6008 0.2967 0.6571 0.074 Uiso 1 1 calc R . .
C11 C 0.80180(6) 0.6042(2) 0.64283(10) 0.0449(4) Uani 1 1 d . . .
C12 C 0.84319(7) 0.5526(2) 0.61140(9) 0.0450(4) Uani 1 1 d . . .
C13 C 0.89869(7) 0.5963(3) 0.64771(11) 0.0516(5) Uani 1 1 d . . .
C14 C 0.90897(7) 0.7010(3) 0.71139(11) 0.0544(5) Uani 1 1 d . . .
H14 H 0.9447 0.7302 0.7352 0.065 Uiso 1 1 calc R . .
C15 C 0.86755(7) 0.7657(2) 0.74188(11) 0.0508(5) Uani 1 1 d . . .
C16 C 0.81302(7) 0.7160(2) 0.70837(10) 0.0465(4) Uani 1 1 d . . .
C17 C 0.77241(8) 0.7847(3) 0.74014(11) 0.0556(5) Uani 1 1 d . . .
H17 H 0.7364 0.7550 0.7190 0.067 Uiso 1 1 calc R . .
C18 C 0.78481(9) 0.8935(3) 0.80114(13) 0.0644(5) Uani 1 1 d . . .
H18 H 0.7573 0.9368 0.8211 0.077 Uiso 1 1 calc R . .
C19 C 0.83858(9) 0.9410(3) 0.83415(13) 0.0688(6) Uani 1 1 d . . .
H19 H 0.8466 1.0148 0.8761 0.083 Uiso 1 1 calc R . .
C20 C 0.87869(8) 0.8797(3) 0.80512(11) 0.0614(5) Uani 1 1 d . . .
H20 H 0.9143 0.9128 0.8269 0.074 Uiso 1 1 calc R . .
C21 C 0.76484(8) 0.5533(3) 0.43063(10) 0.0558(5) Uani 1 1 d . . .
H21A H 0.7601 0.5982 0.3767 0.067 Uiso 1 1 calc R . .
H21B H 0.7453 0.4538 0.4249 0.067 Uiso 1 1 calc R . .
C22 C 0.82395(8) 0.5237(3) 0.46787(11) 0.0561(5) Uani 1 1 d . . .
H22A H 0.8381 0.4564 0.4319 0.067 Uiso 1 1 calc R . .
H22B H 0.8434 0.6232 0.4734 0.067 Uiso 1 1 calc R . .
C23 C 0.63258(7) 0.6047(3) 0.42022(11) 0.0543(5) Uani 1 1 d . . .
H23 H 0.6537 0.6673 0.3953 0.065 Uiso 1 1 calc R . .
C24 C 0.58110(8) 0.5817(3) 0.37618(11) 0.0597(5) Uani 1 1 d . . .
C25 C 0.56153(10) 0.6606(3) 0.29937(13) 0.0730(7) Uani 1 1 d . . .
C26 C 0.54097(9) 0.4818(4) 0.39665(13) 0.0772(7) Uani 1 1 d . . .
C27 C 0.94049(7) 0.5263(3) 0.61474(11) 0.0589(5) Uani 1 1 d . . .
H27 H 0.9288 0.4864 0.5620 0.071 Uiso 1 1 calc R . .
C28 C 0.99387(8) 0.5114(3) 0.65030(12) 0.0658(6) Uani 1 1 d . . .
C29 C 1.01991(8) 0.5576(5) 0.73173(16) 0.0913(10) Uani 1 1 d . . .
C30 C 1.02928(8) 0.4364(4) 0.60767(14) 0.0864(9) Uani 1 1 d . . .
C31 C 0.52685(6) 0.2785(2) 0.98994(10) 0.0479(4) Uani 1 1 d . . .
C32 C 0.53968(7) 0.3987(3) 0.94498(11) 0.0495(4) Uani 1 1 d . . .
C33 C 0.58995(7) 0.4043(3) 0.92350(11) 0.0586(5) Uani 1 1 d . . .
C34 C 0.62716(8) 0.2868(3) 0.95009(12) 0.0630(6) Uani 1 1 d . . .
H34 H 0.6602 0.2901 0.9365 0.076 Uiso 1 1 calc R . .
C35 C 0.61618(7) 0.1614(3) 0.99753(12) 0.0565(5) Uani 1 1 d . . .
C36 C 0.56605(7) 0.1580(3) 1.01985(11) 0.0503(4) Uani 1 1 d . . .
C37 C 0.55835(7) 0.0382(3) 1.07380(11) 0.0559(5) Uani 1 1 d . . .
H37 H 0.5264 0.0357 1.0907 0.067 Uiso 1 1 calc R . .
C38 C 0.59719(9) -0.0736(3) 1.10141(13) 0.0663(6) Uani 1 1 d . . .
H38 H 0.5919 -0.1494 1.1383 0.080 Uiso 1 1 calc R . .
C39 C 0.64446(9) -0.0761(3) 1.07531(15) 0.0735(7) Uani 1 1 d . . .
H39 H 0.6695 -0.1569 1.0921 0.088 Uiso 1 1 calc R . .
C40 C 0.65419(8) 0.0388(3) 1.02542(14) 0.0705(6) Uani 1 1 d . . .
H40 H 0.6864 0.0371 1.0092 0.085 Uiso 1 1 calc R . .
C41 C 0.51606(8) 0.6588(3) 0.96864(14) 0.0637(5) Uani 1 1 d . . .
H41A H 0.5075 0.7528 0.9351 0.076 Uiso 1 1 calc R . .
H41B H 0.5545 0.6608 0.9957 0.076 Uiso 1 1 calc R . .
C42 C 0.59789(9) 0.5333(3) 0.87054(13) 0.0708(6) Uani 1 1 d . . .
H42 H 0.5690 0.5557 0.8259 0.085 Uiso 1 1 calc R . .
C43 C 0.64214(8) 0.6221(3) 0.87954(14) 0.0712(6) Uani 1 1 d . . .
C44 C 0.68710(9) 0.6137(4) 0.95029(16) 0.0760(7) Uani 1 1 d . . .
C45 C 0.64500(10) 0.7423(4) 0.8212(2) 0.0962(9) 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 C25 1.132(3) . ?
N2 C26 1.146(3) . ?
N3 C29 1.131(3) . ?
N4 C30 1.137(3) . ?
N5 C44 1.138(3) . ?
N6 C45 1.144(4) . ?
O1 C2 1.374(2) . ?
O1 C21 1.446(2) . ?
O2 C12 1.373(2) . ?
O2 C22 1.443(2) . ?
O3 C32 1.377(2) . ?
O3 C41 1.440(3) . ?
C1 C2 1.367(2) . ?
C1 C6 1.432(3) . ?
C1 C11 1.497(2) . ?
C2 C3 1.438(2) . ?
C3 C4 1.369(3) . ?
C3 C23 1.452(2) . ?
C4 C5 1.399(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.412(3) . ?
C5 C6 1.426(2) . ?
C6 C7 1.410(3) . ?
C7 C8 1.358(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.370(2) . ?
C11 C16 1.432(3) . ?
C12 C13 1.439(2) . ?
C13 C14 1.370(3) . ?
C13 C27 1.451(3) . ?
C14 C15 1.401(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.417(3) . ?
C15 C16 1.424(2) . ?
C16 C17 1.409(3) . ?
C17 C18 1.361(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.348(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.498(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.347(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.435(3) . ?
C24 C26 1.437(4) . ?
C27 C28 1.345(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.425(3) . ?
C28 C30 1.441(3) . ?
C31 C32 1.361(3) . ?
C31 C36 1.427(3) . ?
C31 C31 1.493(3) 2_657 ?
C32 C33 1.420(2) . ?
C33 C34 1.369(3) . ?
C33 C42 1.461(3) . ?
C34 C35 1.403(3) . ?
C34 H34 0.9300 . ?
C35 C40 1.416(3) . ?
C35 C36 1.423(2) . ?
C36 C37 1.413(3) . ?
C37 C38 1.363(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.386(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.353(4) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C41 1.500(4) 2_657 ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.331(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.433(3) . ?
C43 C45 1.434(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 O1 C21 112.89(15) . . ?
C12 O2 C22 114.62(15) . . ?
C32 O3 C41 112.69(13) . . ?
C2 C1 C6 119.15(15) . . ?
C2 C1 C11 120.86(15) . . ?
C6 C1 C11 119.99(14) . . ?
C1 C2 O1 120.03(14) . . ?
C1 C2 C3 121.74(16) . . ?
O1 C2 C3 118.17(15) . . ?
C4 C3 C2 118.27(15) . . ?
C4 C3 C23 124.07(16) . . ?
C2 C3 C23 117.59(17) . . ?
C3 C4 C5 122.00(16) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C10 121.31(16) . . ?
C4 C5 C6 119.39(17) . . ?
C10 C5 C6 119.27(16) . . ?
C7 C6 C5 117.50(17) . . ?
C7 C6 C1 123.43(15) . . ?
C5 C6 C1 119.03(15) . . ?
C8 C7 C6 121.28(17) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 121.28(19) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C5 121.38(17) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C12 C11 C16 119.53(15) . . ?
C12 C11 C1 121.21(16) . . ?
C16 C11 C1 119.26(15) . . ?
C11 C12 O2 120.71(15) . . ?
C11 C12 C13 121.48(16) . . ?
O2 C12 C13 117.70(16) . . ?
C14 C13 C12 118.17(17) . . ?
C14 C13 C27 123.89(16) . . ?
C12 C13 C27 117.94(17) . . ?
C13 C14 C15 122.31(16) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C20 121.51(17) . . ?
C14 C15 C16 119.21(17) . . ?
C20 C15 C16 119.28(18) . . ?
C17 C16 C15 117.59(17) . . ?
C17 C16 C11 123.36(16) . . ?
C15 C16 C11 119.02(17) . . ?
C18 C17 C16 121.34(18) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 121.04(18) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
O1 C21 C22 111.37(15) . . ?
O1 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O1 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
O2 C22 C21 111.83(15) . . ?
O2 C22 H22A 109.3 . . ?
C21 C22 H22A 109.2 . . ?
O2 C22 H22B 109.2 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C3 129.7(2) . . ?
C24 C23 H23 115.1 . . ?
C3 C23 H23 115.1 . . ?
C23 C24 C25 119.9(2) . . ?
C23 C24 C26 127.1(2) . . ?
C25 C24 C26 113.00(18) . . ?
N1 C25 C24 177.5(3) . . ?
N2 C26 C24 174.8(2) . . ?
C28 C27 C13 128.60(19) . . ?
C28 C27 H27 115.7 . . ?
C13 C27 H27 115.7 . . ?
C27 C28 C29 125.0(2) . . ?
C27 C28 C30 120.5(2) . . ?
C29 C28 C30 114.33(19) . . ?
N3 C29 C28 178.5(4) . . ?
N4 C30 C28 179.4(3) . . ?
C32 C31 C36 119.12(16) . . ?
C32 C31 C31 119.63(13) . 2_657 ?
C36 C31 C31 121.19(14) . 2_657 ?
C31 C32 O3 120.93(16) . . ?
C31 C32 C33 122.11(19) . . ?
O3 C32 C33 116.96(18) . . ?
C34 C33 C32 119.0(2) . . ?
C34 C33 C42 123.53(18) . . ?
C32 C33 C42 117.4(2) . . ?
C33 C34 C35 121.05(17) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C40 121.75(19) . . ?
C34 C35 C36 119.53(19) . . ?
C40 C35 C36 118.7(2) . . ?
C37 C36 C35 118.07(18) . . ?
C37 C36 C31 122.83(17) . . ?
C35 C36 C31 119.04(19) . . ?
C38 C37 C36 120.8(2) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C39 121.0(2) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C40 C39 C38 120.2(2) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C35 121.1(2) . . ?
C39 C40 H40 119.5 . . ?
C35 C40 H40 119.5 . . ?
O3 C41 C41 110.60(13) . 2_657 ?
O3 C41 H41A 109.5 . . ?
C41 C41 H41A 109.5 2_657 . ?
O3 C41 H41B 109.5 . . ?
C41 C41 H41B 109.5 2_657 . ?
H41A C41 H41B 108.1 . . ?
C43 C42 C33 126.8(2) . . ?
C43 C42 H42 116.6 . . ?
C33 C42 H42 116.6 . . ?
C42 C43 C44 122.7(2) . . ?
C42 C43 C45 120.9(2) . . ?
C44 C43 C45 116.2(2) . . ?
N5 C44 C43 177.6(3) . . ?
N6 C45 C43 179.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1823472'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H22 N4 O2'
_chemical_formula_weight         506.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   12.0721(6)
_cell_length_b                   17.9566(12)
_cell_length_c                   12.2305(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2651.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2985
_cell_measurement_theta_min      4.3920
_cell_measurement_theta_max      71.5610

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7822
_exptl_absorpt_correction_T_max  0.8055
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0356
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6673
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.93
_diffrn_reflns_theta_max         66.04
_reflns_number_total             2286
_reflns_number_gt                2039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0603P)²+0.2303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         2286
_refine_ls_number_parameters     200
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.119
_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
O1 O 0.20958(14) -0.03447(9) 0.66895(15) 0.0852(6) Uani 1 1 d D . .
N1 N 0.3354(2) 0.09043(15) 1.06883(17) 0.0916(7) Uani 1 1 d . . .
N2 N 0.2763(3) 0.27185(17) 0.8401(2) 0.1148(10) Uani 1 1 d . . .
C1 C 0.10556(16) 0.03288(12) 0.53694(15) 0.0513(5) Uani 1 1 d . . .
C2 C 0.16075(17) 0.03011(12) 0.63560(17) 0.0583(5) Uani 1 1 d . . .
C3 C 0.16350(16) 0.09262(12) 0.70778(15) 0.0560(5) Uani 1 1 d . . .
C4 C 0.11401(17) 0.15770(12) 0.67494(16) 0.0564(5) Uani 1 1 d . . .
H4 H 0.1185 0.1993 0.7200 0.068 Uiso 1 1 calc R . .
C5 C 0.05690(16) 0.16316(12) 0.57537(15) 0.0536(5) Uani 1 1 d . . .
C6 C 0.04983(15) 0.09963(12) 0.50617(15) 0.0514(5) Uani 1 1 d . . .
C7 C -0.01371(19) 0.10540(13) 0.41018(16) 0.0611(5) Uani 1 1 d . . .
H7 H -0.0194 0.0643 0.3642 0.073 Uiso 1 1 calc R . .
C8 C -0.0668(2) 0.16912(15) 0.38280(19) 0.0719(7) Uani 1 1 d . . .
H8 H -0.1089 0.1711 0.3192 0.086 Uiso 1 1 calc R . .
C9 C -0.0585(2) 0.23174(16) 0.4497(2) 0.0783(8) Uani 1 1 d . . .
H9 H -0.0942 0.2756 0.4299 0.094 Uiso 1 1 calc R . .
C10 C 0.0018(2) 0.22911(13) 0.5442(2) 0.0664(6) Uani 1 1 d . . .
H10 H 0.0066 0.2712 0.5883 0.080 Uiso 1 1 calc R . .
C11 C 0.21248(18) 0.08202(13) 0.81556(17) 0.0611(6) Uani 1 1 d . . .
H11 H 0.2129 0.0331 0.8407 0.073 Uiso 1 1 calc R . .
C12 C 0.25684(17) 0.13201(13) 0.88370(16) 0.0605(5) Uani 1 1 d . . .
C13 C 0.29980(18) 0.10937(14) 0.98729(17) 0.0666(6) Uani 1 1 d . . .
C14 C 0.2674(2) 0.21013(17) 0.85904(19) 0.0758(7) Uani 1 1 d . . .
C15 C 0.3054(6) -0.0662(4) 0.6478(6) 0.091(2) Uani 0.50 1 d PDU . .
H15A H 0.3025 -0.0986 0.5854 0.109 Uiso 0.50 1 d PR . .
H15B H 0.3245 -0.0954 0.7109 0.109 Uiso 0.50 1 d PR . .
C16 C 0.3920(6) -0.0088(5) 0.6354(6) 0.098(2) Uani 0.50 1 d PDU . .
H16A H 0.4637 -0.0320 0.6356 0.117 Uiso 0.50 1 d PR . .
H16B H 0.3893 0.0233 0.6981 0.117 Uiso 0.50 1 d PR . .
C17 C 0.3875(5) 0.0414(4) 0.5319(5) 0.0798(16) Uani 0.50 1 d PDU . .
H17A H 0.4455 0.0779 0.5354 0.096 Uiso 0.50 1 d PR . .
H17B H 0.3180 0.0674 0.5312 0.096 Uiso 0.50 1 d PR . .
C18 C 0.3980(5) -0.0020(5) 0.4279(5) 0.0804(18) Uani 0.50 1 d PDU . .
H18A H 0.3717 -0.0517 0.4405 0.096 Uiso 0.50 1 d PR . .
H18B H 0.4751 -0.0052 0.4091 0.096 Uiso 0.50 1 d PR . .
C19 C 0.3358(5) 0.0306(4) 0.3293(5) 0.0698(17) Uani 0.50 1 d PDU . .
H19A H 0.3568 0.0031 0.2653 0.084 Uiso 0.50 1 d PR . .
H19B H 0.3623 0.0805 0.3195 0.084 Uiso 0.50 1 d PR . .


_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 C15 1.316(6) . ?
O1 C2 1.363(2) . ?
O1 C19 1.525(6) 3_556 ?
N1 C13 1.138(3) . ?
N2 C14 1.137(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.425(3) . ?
C1 C1 1.487(4) 3_556 ?
C2 C3 1.428(3) . ?
C3 C4 1.373(3) . ?
C3 C11 1.457(3) . ?
C4 C5 1.403(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.411(3) . ?
C5 C6 1.423(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.353(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.337(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.428(3) . ?
C12 C14 1.441(4) . ?
C15 C19 0.789(8) 3_556 ?
C15 C16 1.476(8) . ?
C15 C18 1.900(10) 3_556 ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C16 C18 0.802(7) 3_556 ?
C16 C19 0.894(8) 3_556 ?
C16 C17 1.556(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9601 . ?
C17 C18 0.871(8) 3_556 ?
C17 C18 1.498(6) . ?
C17 C17 1.680(13) 3_556 ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C18 C16 0.802(7) 3_556 ?
C18 C17 0.871(8) 3_556 ?
C18 C19 1.537(7) . ?
C18 C18 1.765(12) 3_556 ?
C18 C15 1.900(10) 3_556 ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C19 C15 0.789(8) 3_556 ?
C19 C16 0.894(8) 3_556 ?
C19 O1 1.525(6) 3_556 ?
C19 H19A 0.9600 . ?
C19 H19B 0.9599 . ?

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
C15 O1 C2 133.7(4) . . ?
C15 O1 C19 31.2(3) . 3_556 ?
C2 O1 C19 113.4(3) . 3_556 ?
C2 C1 C6 119.30(18) . . ?
C2 C1 C1 120.2(2) . 3_556 ?
C6 C1 C1 120.49(18) . 3_556 ?
O1 C2 C1 120.08(19) . . ?
O1 C2 C3 118.26(17) . . ?
C1 C2 C3 121.57(19) . . ?
C4 C3 C2 118.56(18) . . ?
C4 C3 C11 123.54(19) . . ?
C2 C3 C11 117.76(19) . . ?
C3 C4 C5 121.84(19) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C10 121.67(19) . . ?
C4 C5 C6 119.32(19) . . ?
C10 C5 C6 118.94(18) . . ?
C7 C6 C5 118.04(19) . . ?
C7 C6 C1 122.69(19) . . ?
C5 C6 C1 119.27(16) . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C3 129.7(2) . . ?
C12 C11 H11 115.1 . . ?
C3 C11 H11 115.1 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 C14 124.0(2) . . ?
C13 C12 C14 115.5(2) . . ?
N1 C13 C12 178.7(3) . . ?
N2 C14 C12 179.5(3) . . ?
C19 C15 O1 89.2(8) 3_556 . ?
C19 C15 C16 30.8(7) 3_556 . ?
O1 C15 C16 109.9(6) . . ?
C19 C15 C18 51.4(7) 3_556 3_556 ?
O1 C15 C18 109.5(5) . 3_556 ?
C16 C15 C18 23.4(3) . 3_556 ?
C19 C15 H15A 142.2 3_556 . ?
O1 C15 H15A 112.7 . . ?
C16 C15 H15A 111.5 . . ?
C18 C15 H15A 91.4 3_556 . ?
C19 C15 H15B 92.6 3_556 . ?
O1 C15 H15B 106.8 . . ?
C16 C15 H15B 107.1 . . ?
C18 C15 H15B 127.0 3_556 . ?
H15A C15 H15B 108.6 . . ?
C18 C16 C19 129.9(11) 3_556 3_556 ?
C18 C16 C15 109.4(9) 3_556 . ?
C19 C16 C15 26.8(6) 3_556 . ?
C18 C16 C17 22.5(8) 3_556 . ?
C19 C16 C17 128.3(8) 3_556 . ?
C15 C16 C17 117.7(5) . . ?
C18 C16 H16A 91.5 3_556 . ?
C19 C16 H16A 119.6 3_556 . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 106.5 . . ?
C18 C16 H16B 129.0 3_556 . ?
C19 C16 H16B 81.4 3_556 . ?
C15 C16 H16B 108.3 . . ?
C17 C16 H16B 107.5 . . ?
H16A C16 H16B 106.8 . . ?
C18 C17 C18 92.5(8) 3_556 . ?
C18 C17 C16 20.6(7) 3_556 . ?
C18 C17 C16 112.7(6) . . ?
C18 C17 C17 62.8(7) 3_556 3_556 ?
C18 C17 C17 31.2(3) . 3_556 ?
C16 C17 C17 82.2(5) . 3_556 ?
C18 C17 H17A 115.1 3_556 . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.5 . . ?
C17 C17 H17A 128.7 3_556 . ?
C18 C17 H17B 121.7 3_556 . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C17 C17 H17B 115.2 3_556 . ?
H17A C17 H17B 107.9 . . ?
C16 C18 C17 136.8(14) 3_556 3_556 ?
C16 C18 C17 133.3(11) 3_556 . ?
C17 C18 C17 86.1(8) 3_556 . ?
C16 C18 C19 26.5(6) 3_556 . ?
C17 C18 C19 132.9(9) 3_556 . ?
C17 C18 C19 115.3(6) . . ?
C16 C18 C18 162.8(13) 3_556 3_556 ?
C17 C18 C18 58.0(6) 3_556 3_556 ?
C17 C18 C18 29.5(4) . 3_556 ?
C19 C18 C18 140.2(6) . 3_556 ?
C16 C18 C15 47.1(7) 3_556 3_556 ?
C17 C18 C15 135.6(8) 3_556 3_556 ?
C17 C18 C15 91.6(5) . 3_556 ?
C19 C18 C15 23.7(3) . 3_556 ?
C18 C18 C15 117.4(6) 3_556 3_556 ?
C16 C18 H18A 110.5 3_556 . ?
C17 C18 H18A 26.6 3_556 . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.6 . . ?
C18 C18 H18A 83.0 3_556 . ?
C15 C18 H18A 118.9 3_556 . ?
C16 C18 H18B 82.6 3_556 . ?
C17 C18 H18B 103.2 3_556 . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.0 . . ?
C18 C18 H18B 104.0 3_556 . ?
C15 C18 H18B 119.4 3_556 . ?
H18A C18 H18B 107.7 . . ?
C15 C19 C16 122.4(12) 3_556 3_556 ?
C15 C19 O1 59.6(7) 3_556 3_556 ?
C16 C19 O1 140.5(8) 3_556 3_556 ?
C15 C19 C18 104.9(9) 3_556 . ?
C16 C19 C18 23.6(5) 3_556 . ?
O1 C19 C18 119.7(4) 3_556 . ?
C15 C19 H19A 146.0 3_556 . ?
C16 C19 H19A 88.2 3_556 . ?
O1 C19 H19A 107.4 3_556 . ?
C18 C19 H19A 108.4 . . ?
C15 C19 H19B 56.0 3_556 . ?
C16 C19 H19B 102.4 3_556 . ?
O1 C19 H19B 107.0 3_556 . ?
C18 C19 H19B 106.9 . . ?
H19A C19 H19B 106.8 . . ?

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
C15 O1 C2 C1 82.9(5) . . . . ?
C19 O1 C2 C1 111.7(3) 3_556 . . . ?
C15 O1 C2 C3 -100.4(5) . . . . ?
C19 O1 C2 C3 -71.5(4) 3_556 . . . ?
C6 C1 C2 O1 176.57(18) . . . . ?
C1 C1 C2 O1 -4.2(3) 3_556 . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C1 C2 C3 179.20(17) 3_556 . . . ?
O1 C2 C3 C4 -179.67(18) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
O1 C2 C3 C11 -3.7(3) . . . . ?
C1 C2 C3 C11 172.95(18) . . . . ?
C2 C3 C4 C5 3.0(3) . . . . ?
C11 C3 C4 C5 -172.70(18) . . . . ?
C3 C4 C5 C10 177.04(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 176.11(19) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C4 C5 C6 C1 -3.1(3) . . . . ?
C10 C5 C6 C1 179.80(18) . . . . ?
C2 C1 C6 C7 -176.08(19) . . . . ?
C1 C1 C6 C7 4.7(3) 3_556 . . . ?
C2 C1 C6 C5 3.1(3) . . . . ?
C1 C1 C6 C5 -176.16(14) 3_556 . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C1 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C4 C5 C10 C9 -176.3(2) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C4 C3 C11 C12 -27.7(4) . . . . ?
C2 C3 C11 C12 156.6(2) . . . . ?
C3 C11 C12 C13 179.42(19) . . . . ?
C3 C11 C12 C14 -2.0(4) . . . . ?
C11 C12 C13 N1 59(14) . . . . ?
C14 C12 C13 N1 -119(14) . . . . ?
C11 C12 C14 N2 -156(100) . . . . ?
C13 C12 C14 N2 22(52) . . . . ?
C2 O1 C15 C19 58.8(11) . . . 3_556 ?
C2 O1 C15 C16 35.6(8) . . . . ?
C19 O1 C15 C16 -23.3(6) 3_556 . . . ?
C2 O1 C15 C18 10.6(8) . . . 3_556 ?
C19 O1 C15 C18 -48.2(7) 3_556 . . 3_556 ?
C19 C15 C16 C18 -143.8(18) 3_556 . . 3_556 ?
O1 C15 C16 C18 -93.3(11) . . . 3_556 ?
O1 C15 C16 C19 50.5(12) . . . 3_556 ?
C18 C15 C16 C19 143.8(18) 3_556 . . 3_556 ?
C19 C15 C16 C17 -120.9(15) 3_556 . . . ?
O1 C15 C16 C17 -70.4(8) . . . . ?
C18 C15 C16 C17 22.9(7) 3_556 . . . ?
C19 C16 C17 C18 -103(2) 3_556 . . 3_556 ?
C15 C16 C17 C18 -73.6(17) . . . 3_556 ?
C18 C16 C17 C18 12.6(14) 3_556 . . . ?
C19 C16 C17 C18 -90.6(13) 3_556 . . . ?
C15 C16 C17 C18 -61.0(9) . . . . ?
C18 C16 C17 C17 19.0(17) 3_556 . . 3_556 ?
C19 C16 C17 C17 -84.2(11) 3_556 . . 3_556 ?
C15 C16 C17 C17 -54.6(6) . . . 3_556 ?
C18 C17 C18 C16 176.8(10) 3_556 . . 3_556 ?
C16 C17 C18 C16 172.4(14) . . . 3_556 ?
C17 C17 C18 C16 160.1(17) 3_556 . . 3_556 ?
C18 C17 C18 C17 16.7(13) 3_556 . . 3_556 ?
C16 C17 C18 C17 12.3(11) . . . 3_556 ?
C18 C17 C18 C19 153.0(6) 3_556 . . . ?
C16 C17 C18 C19 148.6(6) . . . . ?
C17 C17 C18 C19 136.3(10) 3_556 . . . ?
C16 C17 C18 C18 -4.4(5) . . . 3_556 ?
C17 C17 C18 C18 -16.7(13) 3_556 . . 3_556 ?
C18 C17 C18 C15 152.2(7) 3_556 . . 3_556 ?
C16 C17 C18 C15 147.8(6) . . . 3_556 ?
C17 C17 C18 C15 135.6(8) 3_556 . . 3_556 ?
C16 C18 C19 C15 -141(2) 3_556 . . 3_556 ?
C17 C18 C19 C15 107.8(15) 3_556 . . 3_556 ?
C17 C18 C19 C15 -1.8(11) . . . 3_556 ?
C18 C18 C19 C15 18.7(15) 3_556 . . 3_556 ?
C17 C18 C19 C16 -111(2) 3_556 . . 3_556 ?
C17 C18 C19 C16 138.9(19) . . . 3_556 ?
C18 C18 C19 C16 159(2) 3_556 . . 3_556 ?
C15 C18 C19 C16 141(2) 3_556 . . 3_556 ?
C16 C18 C19 O1 156.1(19) 3_556 . . 3_556 ?
C17 C18 C19 O1 44.6(15) 3_556 . . 3_556 ?
C17 C18 C19 O1 -65.0(8) . . . 3_556 ?
C18 C18 C19 O1 -44.5(13) 3_556 . . 3_556 ?
C15 C18 C19 O1 -63.2(8) 3_556 . . 3_556 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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 1823474'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 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 H28 N4 O2'
_chemical_formula_weight         548.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.8302(3)
_cell_length_b                   18.7601(8)
_cell_length_c                   19.0270(7)
_cell_angle_alpha                110.640(4)
_cell_angle_beta                 94.387(3)
_cell_angle_gamma                93.845(3)
_cell_volume                     2926.00(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8971
_cell_measurement_theta_min      4.1350
_cell_measurement_theta_max      69.2690

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8352
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0356
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51563
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         66.09
_reflns_number_total             10228
_reflns_number_gt                6845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0944P)²+0.4419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10228
_refine_ls_number_parameters     868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_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
N1 N 0.4882(5) 0.27411(19) 0.58808(17) 0.1292(12) Uani 1 1 d . . .
N2 N 0.1403(4) 0.4028(2) 0.5442(2) 0.1359(13) Uani 1 1 d . . .
N3 N 1.1830(4) 0.4856(2) 0.05745(19) 0.1345(13) Uani 1 1 d . . .
N4 N 0.8751(4) 0.2874(3) -0.07193(19) 0.1474(15) Uani 1 1 d . . .
N5 N 0.3946(4) 0.09232(19) 1.06405(15) 0.1081(9) Uani 1 1 d . . .
N6 N 0.8482(4) 0.1240(2) 1.01624(18) 0.1454(14) Uani 1 1 d . . .
N7 N -0.2104(3) 0.28019(14) 0.47621(13) 0.0869(7) Uani 1 1 d . . .
N8 N 0.2077(3) 0.18406(14) 0.40631(15) 0.0882(7) Uani 1 1 d . . .
O1 O 0.55463(17) 0.30330(8) 0.30640(8) 0.0568(4) Uani 1 1 d . . .
O2 O 0.74847(18) 0.45320(9) 0.24838(9) 0.0650(4) Uani 1 1 d . . .
O3 O 0.48376(19) 0.09394(11) 0.74855(9) 0.0693(5) Uani 1 1 d . . .
O4 O 0.0176(2) 0.15645(11) 0.68809(10) 0.0786(5) Uani 1 1 d . . .
C1 C 0.4504(2) 0.40310(12) 0.27430(12) 0.0500(5) Uani 1 1 d . . .
C2 C 0.4735(2) 0.36579(12) 0.32368(12) 0.0498(5) Uani 1 1 d . . .
C3 C 0.4226(2) 0.39233(13) 0.39713(12) 0.0523(5) Uani 1 1 d . . .
C4 C 0.3408(3) 0.45481(13) 0.41607(13) 0.0564(6) Uani 1 1 d . . .
H4 H 0.3091 0.4735 0.4642 0.068 Uiso 1 1 calc R . .
C5 C 0.3034(3) 0.49133(13) 0.36547(13) 0.0547(6) Uani 1 1 d . . .
C6 C 0.3599(2) 0.46613(12) 0.29381(12) 0.0513(5) Uani 1 1 d . . .
C7 C 0.3173(3) 0.50281(14) 0.24325(14) 0.0615(6) Uani 1 1 d . . .
H7 H 0.3545 0.4883 0.1963 0.074 Uiso 1 1 calc R . .
C8 C 0.2224(3) 0.55913(15) 0.26228(17) 0.0743(7) Uani 1 1 d . . .
H8 H 0.1940 0.5820 0.2278 0.089 Uiso 1 1 calc R . .
C9 C 0.1672(3) 0.58320(16) 0.33264(17) 0.0803(8) Uani 1 1 d . . .
H9 H 0.1019 0.6217 0.3446 0.096 Uiso 1 1 calc R . .
C10 C 0.2079(3) 0.55088(14) 0.38382(16) 0.0698(7) Uani 1 1 d . . .
H10 H 0.1726 0.5681 0.4312 0.084 Uiso 1 1 calc R . .
C11 C 0.4646(3) 0.35383(14) 0.44873(13) 0.0591(6) Uani 1 1 d . . .
H11 H 0.5518 0.3282 0.4398 0.071 Uiso 1 1 calc R . .
C12 C 0.3943(3) 0.35030(14) 0.50750(14) 0.0652(7) Uani 1 1 d . . .
C13 C 0.4489(4) 0.30826(18) 0.55197(16) 0.0855(9) Uani 1 1 d . . .
C14 C 0.2543(4) 0.38114(18) 0.52743(18) 0.0880(9) Uani 1 1 d . . .
C15 C 0.5091(2) 0.37762(12) 0.19824(12) 0.0496(5) Uani 1 1 d . . .
C16 C 0.6513(3) 0.40469(13) 0.18866(12) 0.0525(5) Uani 1 1 d . . .
C17 C 0.6991(3) 0.38715(14) 0.11465(13) 0.0574(6) Uani 1 1 d . . .
C18 C 0.6009(3) 0.34226(15) 0.05349(14) 0.0647(6) Uani 1 1 d . . .
H18 H 0.6314 0.3314 0.0054 0.078 Uiso 1 1 calc R . .
C19 C 0.4559(3) 0.31214(14) 0.06068(13) 0.0583(6) Uani 1 1 d . . .
C20 C 0.4090(3) 0.33030(13) 0.13430(12) 0.0515(5) Uani 1 1 d . . .
C21 C 0.2613(3) 0.30117(14) 0.14004(14) 0.0625(6) Uani 1 1 d . . .
H21 H 0.2271 0.3127 0.1875 0.075 Uiso 1 1 calc R . .
C22 C 0.1673(3) 0.25655(16) 0.07779(15) 0.0720(7) Uani 1 1 d . . .
H22 H 0.0704 0.2379 0.0832 0.086 Uiso 1 1 calc R . .
C23 C 0.2152(3) 0.23845(17) 0.00566(15) 0.0766(8) Uani 1 1 d . . .
H23 H 0.1504 0.2077 -0.0366 0.092 Uiso 1 1 calc R . .
C24 C 0.3545(3) 0.26557(16) -0.00243(14) 0.0712(7) Uani 1 1 d . . .
H24 H 0.3851 0.2535 -0.0506 0.085 Uiso 1 1 calc R . .
C25 C 0.8472(3) 0.42254(15) 0.10869(15) 0.0666(7) Uani 1 1 d . . .
H25 H 0.8883 0.4643 0.1509 0.080 Uiso 1 1 calc R . .
C26 C 0.9326(3) 0.40314(18) 0.05060(16) 0.0750(8) Uani 1 1 d . . .
C27 C 1.0721(4) 0.4488(2) 0.05478(18) 0.0947(10) Uani 1 1 d . . .
C28 C 0.8979(3) 0.3386(3) -0.0174(2) 0.0972(11) Uani 1 1 d . . .
C29 C 0.4724(3) 0.23043(14) 0.26889(18) 0.0797(8) Uani 1 1 d . A .
H29A H 0.4504 0.2218 0.2156 0.096 Uiso 1 1 calc R . .
H29B H 0.3762 0.2284 0.2899 0.096 Uiso 1 1 calc R . .
C30 C 0.5632(3) 0.17027(16) 0.27798(18) 0.0788(8) Uani 1 1 d . . .
H30A H 0.6089 0.1872 0.3299 0.095 Uiso 0.604(6) 1 calc PR A 1
H30B H 0.4948 0.1245 0.2688 0.095 Uiso 0.604(6) 1 calc PR A 1
H30C H 0.5262 0.1233 0.2363 0.095 Uiso 0.396(6) 1 d PR A 2
H30D H 0.5370 0.1626 0.3236 0.095 Uiso 0.396(6) 1 d PR A 2
C31 C 0.6825(7) 0.1506(3) 0.2290(4) 0.0830(17) Uani 0.604(6) 1 d P A 1
H31A H 0.6334 0.1234 0.1782 0.100 Uiso 0.604(6) 1 calc PR A 1
H31B H 0.7391 0.1143 0.2433 0.100 Uiso 0.604(6) 1 calc PR A 1
C32 C 0.795(2) 0.2105(7) 0.2250(7) 0.079(3) Uani 0.604(6) 1 d P A 1
H32A H 0.7414 0.2444 0.2059 0.095 Uiso 0.604(6) 1 calc PR A 1
H32B H 0.8644 0.1861 0.1886 0.095 Uiso 0.604(6) 1 calc PR A 1
C33 C 0.8889(5) 0.2584(3) 0.2983(3) 0.0741(16) Uani 0.604(6) 1 d P A 1
H33A H 0.9394 0.2237 0.3177 0.089 Uiso 0.604(6) 1 calc PR A 1
H33B H 0.8186 0.2828 0.3340 0.089 Uiso 0.604(6) 1 calc PR A 1
C34 C 1.009(4) 0.3197(19) 0.2986(18) 0.097(6) Uani 0.604(6) 1 d P A 1
H34A H 1.0974 0.2963 0.2770 0.116 Uiso 0.604(6) 1 calc PR A 1
H34B H 1.0407 0.3537 0.3502 0.116 Uiso 0.604(6) 1 calc PR A 1
C31' C 0.7373(10) 0.1772(5) 0.2817(5) 0.074(2) Uani 0.396(6) 1 d P A 2
H31C H 0.7749 0.2209 0.3267 0.089 Uiso 0.396(6) 1 calc PR A 2
H31D H 0.7703 0.1323 0.2902 0.089 Uiso 0.396(6) 1 calc PR A 2
C32' C 0.819(3) 0.1852(11) 0.2192(14) 0.091(5) Uani 0.396(6) 1 d P A 2
H32C H 0.7609 0.2148 0.1960 0.109 Uiso 0.396(6) 1 calc PR A 2
H32D H 0.8205 0.1347 0.1813 0.109 Uiso 0.396(6) 1 calc PR A 2
C33' C 0.9806(9) 0.2227(5) 0.2410(4) 0.081(3) Uani 0.396(6) 1 d P A 2
H33C H 1.0349 0.1972 0.2700 0.097 Uiso 0.396(6) 1 calc PR A 2
H33D H 1.0295 0.2141 0.1951 0.097 Uiso 0.396(6) 1 calc PR A 2
C34' C 0.999(6) 0.307(3) 0.286(2) 0.084(7) Uani 0.396(6) 1 d P A 2
H34C H 1.1073 0.3208 0.3018 0.101 Uiso 0.396(6) 1 calc PR A 2
H34D H 0.9489 0.3139 0.3308 0.101 Uiso 0.396(6) 1 calc PR A 2
C35 C 0.9441(3) 0.36565(19) 0.25254(18) 0.0856(9) Uani 1 1 d . . .
H35A H 1.0271 0.3959 0.2424 0.103 Uiso 0.604(6) 1 calc PR A 1
H35B H 0.8936 0.3306 0.2045 0.103 Uiso 0.604(6) 1 calc PR A 1
H35C H 1.0327 0.3978 0.2501 0.103 Uiso 0.396(6) 1 d PR A 2
H35D H 0.8986 0.3386 0.2010 0.103 Uiso 0.396(6) 1 d PR A 2
C36 C 0.8328(3) 0.41745(17) 0.29407(15) 0.0757(8) Uani 1 1 d . A .
H36A H 0.7606 0.3882 0.3119 0.091 Uiso 1 1 calc R . .
H36B H 0.8877 0.4573 0.3380 0.091 Uiso 1 1 calc R . .
C37 C 0.2143(3) 0.05832(12) 0.73353(12) 0.0510(5) Uani 1 1 d . . .
C38 C 0.3523(3) 0.07604(13) 0.77619(13) 0.0551(6) Uani 1 1 d . B .
C39 C 0.3723(3) 0.06946(13) 0.84912(12) 0.0565(6) Uani 1 1 d . . .
C40 C 0.2466(3) 0.04314(13) 0.87482(13) 0.0605(6) Uani 1 1 d . B .
H40 H 0.2575 0.0384 0.9219 0.073 Uiso 1 1 calc R . .
C41 C 0.1037(3) 0.02333(13) 0.83297(12) 0.0571(6) Uani 1 1 d . . .
C42 C 0.0851(3) 0.03127(12) 0.76125(12) 0.0538(6) Uani 1 1 d . B .
C43 C -0.0600(3) 0.00964(15) 0.72029(14) 0.0656(6) Uani 1 1 d . . .
H43 H -0.0756 0.0150 0.6736 0.079 Uiso 1 1 calc R B .
C44 C -0.1779(3) -0.01882(17) 0.74717(16) 0.0801(8) Uani 1 1 d . B .
H44 H -0.2728 -0.0325 0.7187 0.096 Uiso 1 1 calc R . .
C45 C -0.1594(3) -0.02796(18) 0.81713(17) 0.0826(8) Uani 1 1 d . . .
H45 H -0.2410 -0.0482 0.8347 0.099 Uiso 1 1 calc R B .
C46 C -0.0221(3) -0.00711(16) 0.85885(15) 0.0742(7) Uani 1 1 d . B .
H46 H -0.0101 -0.0129 0.9055 0.089 Uiso 1 1 calc R . .
C47 C 0.5230(3) 0.08775(14) 0.89024(14) 0.0675(7) Uani 1 1 d . B .
H47 H 0.6022 0.0925 0.8621 0.081 Uiso 1 1 calc R . .
C48 C 0.5661(3) 0.09892(15) 0.96296(14) 0.0716(7) Uani 1 1 d . . .
C49 C 0.4676(4) 0.09565(17) 1.01849(16) 0.0775(8) Uani 1 1 d . B .
C50 C 0.7232(4) 0.1135(2) 0.99155(17) 0.0986(10) Uani 1 1 d . B .
C51 C 0.1969(3) 0.06189(12) 0.65586(12) 0.0511(5) Uani 1 1 d . B .
C52 C 0.1076(3) 0.11165(13) 0.63807(12) 0.0552(6) Uani 1 1 d . B .
C53 C 0.0923(3) 0.11475(13) 0.56419(12) 0.0530(5) Uani 1 1 d . . .
C54 C 0.1636(3) 0.06451(13) 0.50923(12) 0.0538(6) Uani 1 1 d . B .
H54 H 0.1544 0.0665 0.4610 0.065 Uiso 1 1 calc R . .
C55 C 0.2498(2) 0.01020(12) 0.52303(12) 0.0503(5) Uani 1 1 d . . .
C56 C 0.2694(2) 0.00891(12) 0.59741(12) 0.0486(5) Uani 1 1 d . B .
C57 C 0.3542(3) -0.04787(13) 0.60877(13) 0.0562(6) Uani 1 1 d . . .
H57 H 0.3680 -0.0503 0.6568 0.067 Uiso 1 1 calc R B .
C58 C 0.4163(3) -0.09902(14) 0.55119(14) 0.0618(6) Uani 1 1 d . B .
H58 H 0.4724 -0.1356 0.5605 0.074 Uiso 1 1 calc R . .
C59 C 0.3971(3) -0.09752(14) 0.47835(14) 0.0632(6) Uani 1 1 d . . .
H59 H 0.4399 -0.1330 0.4394 0.076 Uiso 1 1 calc R B .
C60 C 0.3162(3) -0.04444(13) 0.46450(13) 0.0598(6) Uani 1 1 d . B .
H60 H 0.3038 -0.0437 0.4158 0.072 Uiso 1 1 calc R . .
C61 C -0.0064(3) 0.16735(13) 0.54875(13) 0.0595(6) Uani 1 1 d . B .
H61 H -0.0829 0.1819 0.5804 0.071 Uiso 1 1 calc R . .
C62 C -0.0019(3) 0.19773(13) 0.49474(13) 0.0576(6) Uani 1 1 d . . .
C63 C -0.1169(3) 0.24456(14) 0.48499(13) 0.0648(7) Uani 1 1 d . B .
C64 C 0.1144(3) 0.18867(14) 0.44509(15) 0.0639(7) Uani 1 1 d . B .
C65 C 0.5057(4) 0.16163(19) 0.73245(19) 0.0626(11) Uani 0.745(5) 1 d P B 1
H65A H 0.4167 0.1666 0.7019 0.075 Uiso 0.745(5) 1 calc PR B 1
H65B H 0.5935 0.1600 0.7045 0.075 Uiso 0.745(5) 1 calc PR B 1
C66 C 0.5308(7) 0.2288(3) 0.8063(3) 0.1018(17) Uani 0.745(5) 1 d P B 1
H66A H 0.4405 0.2298 0.8325 0.122 Uiso 0.745(5) 1 calc PR B 1
H66B H 0.6152 0.2204 0.8372 0.122 Uiso 0.745(5) 1 calc PR B 1
C67 C 0.5637(14) 0.3054(6) 0.8005(6) 0.122(4) Uani 0.745(5) 1 d P B 1
H67A H 0.6051 0.3421 0.8496 0.147 Uiso 0.745(5) 1 calc PR B 1
H67B H 0.6400 0.3025 0.7658 0.147 Uiso 0.745(5) 1 calc PR B 1
C68 C 0.4250(9) 0.3321(5) 0.7738(5) 0.122(2) Uani 0.745(5) 1 d P B 1
H68A H 0.3741 0.2913 0.7294 0.147 Uiso 0.745(5) 1 calc PR B 1
H68B H 0.4545 0.3750 0.7590 0.147 Uiso 0.745(5) 1 calc PR B 1
C69 C 0.3138(14) 0.3563(7) 0.8325(7) 0.136(4) Uani 0.745(5) 1 d P B 1
H69A H 0.3488 0.4066 0.8696 0.163 Uiso 0.745(5) 1 calc PR B 1
H69B H 0.3049 0.3202 0.8584 0.163 Uiso 0.745(5) 1 calc PR B 1
C70 C 0.1601(8) 0.3581(3) 0.7912(4) 0.119(2) Uani 0.745(5) 1 d P B 1
H70A H 0.0881 0.3743 0.8284 0.142 Uiso 0.745(5) 1 calc PR B 1
H70B H 0.1717 0.3971 0.7689 0.142 Uiso 0.745(5) 1 calc PR B 1
C71 C 0.0916(7) 0.2861(3) 0.7312(4) 0.1169(19) Uani 0.745(5) 1 d P B 1
H71A H 0.1470 0.2772 0.6872 0.140 Uiso 0.745(5) 1 calc PR B 1
H71B H -0.0130 0.2923 0.7166 0.140 Uiso 0.745(5) 1 calc PR B 1
C72 C 0.092(2) 0.2170(13) 0.7536(14) 0.085(3) Uani 0.745(5) 1 d P B 1
H72A H 0.1955 0.2070 0.7653 0.103 Uiso 0.745(5) 1 calc PR B 1
H72B H 0.0363 0.2236 0.7971 0.103 Uiso 0.745(5) 1 calc PR B 1
C65' C 0.5806(19) 0.1652(9) 0.7907(9) 0.109(5) Uani 0.255(5) 1 d P B 2
H65C H 0.6774 0.1510 0.8066 0.130 Uiso 0.255(5) 1 calc PR B 2
H65D H 0.5337 0.1908 0.8362 0.130 Uiso 0.255(5) 1 calc PR B 2
C66' C 0.6161(17) 0.2241(8) 0.7548(8) 0.098(5) Uani 0.255(5) 1 d P B 2
H66C H 0.6126 0.1969 0.7008 0.118 Uiso 0.255(5) 1 calc PR B 2
H66D H 0.7206 0.2462 0.7728 0.118 Uiso 0.255(5) 1 calc PR B 2
C67' C 0.516(4) 0.2905(16) 0.7669(16) 0.114(7) Uani 0.255(5) 1 d P B 2
H67C H 0.4163 0.2655 0.7428 0.137 Uiso 0.255(5) 1 calc PR B 2
H67D H 0.5536 0.3164 0.7346 0.137 Uiso 0.255(5) 1 calc PR B 2
C68' C 0.481(3) 0.3575(11) 0.8392(11) 0.107(5) Uani 0.255(5) 1 d P B 2
H68C H 0.4511 0.3389 0.8782 0.128 Uiso 0.255(5) 1 calc PR B 2
H68D H 0.5669 0.3964 0.8595 0.128 Uiso 0.255(5) 1 calc PR B 2
C69' C 0.348(3) 0.3866(12) 0.8051(14) 0.121(7) Uani 0.255(5) 1 d P B 2
H69C H 0.3346 0.3639 0.7504 0.146 Uiso 0.255(5) 1 calc PR B 2
H69D H 0.3586 0.4420 0.8208 0.146 Uiso 0.255(5) 1 calc PR B 2
C70' C 0.218(3) 0.3577(17) 0.841(2) 0.122(8) Uani 0.255(5) 1 d P B 2
H70C H 0.2646 0.3347 0.8743 0.146 Uiso 0.255(5) 1 calc PR B 2
H70D H 0.1736 0.4023 0.8721 0.146 Uiso 0.255(5) 1 calc PR B 2
C71' C 0.0876(18) 0.3012(8) 0.7919(10) 0.097(4) Uani 0.255(5) 1 d P B 2
H71C H 0.0009 0.3185 0.8195 0.116 Uiso 0.255(5) 1 calc PR B 2
H71D H 0.0748 0.3163 0.7482 0.116 Uiso 0.255(5) 1 calc PR B 2
C72' C 0.048(6) 0.216(4) 0.758(4) 0.090(11) Uani 0.255(5) 1 d P B 2
H72C H 0.1284 0.1975 0.7826 0.107 Uiso 0.255(5) 1 calc PR B 2
H72D H -0.0421 0.2092 0.7823 0.107 Uiso 0.255(5) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.143(4) . ?
N2 C14 1.138(4) . ?
N3 C27 1.146(4) . ?
N4 C28 1.131(4) . ?
N5 C49 1.135(4) . ?
N6 C50 1.142(4) . ?
N7 C63 1.135(3) . ?
N8 C64 1.135(3) . ?
O1 C2 1.368(2) . ?
O1 C29 1.416(3) . ?
O2 C16 1.369(3) . ?
O2 C36 1.463(3) . ?
O3 C38 1.379(3) . ?
O3 C65 1.412(4) . ?
O3 C65' 1.465(15) . ?
O4 C52 1.373(3) . ?
O4 C72' 1.39(7) . ?
O4 C72 1.43(3) . ?
C1 C2 1.367(3) . ?
C1 C6 1.428(3) . ?
C1 C15 1.501(3) . ?
C2 C3 1.428(3) . ?
C3 C4 1.372(3) . ?
C3 C11 1.450(3) . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.406(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.358(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.339(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.421(4) . ?
C12 C13 1.424(4) . ?
C15 C16 1.372(3) . ?
C15 C20 1.421(3) . ?
C16 C17 1.433(3) . ?
C17 C18 1.369(3) . ?
C17 C25 1.457(3) . ?
C18 C19 1.400(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.414(3) . ?
C19 C20 1.422(3) . ?
C20 C21 1.407(3) . ?
C21 C22 1.360(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.341(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.343(3) . ?
C25 H25 0.9300 . ?
C26 C28 1.421(5) . ?
C26 C27 1.433(4) . ?
C29 C30 1.478(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.439(6) . ?
C30 C31' 1.528(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
C30 H30D 0.9700 . ?
C31 C32 1.477(18) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.509(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.51(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.54(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C31' C32' 1.48(3) . ?
C31' H31C 0.9700 . ?
C31' H31D 0.9700 . ?
C32' C33' 1.51(3) . ?
C32' H32C 0.9700 . ?
C32' H32D 0.9700 . ?
C33' C34' 1.49(5) . ?
C33' H33C 0.9700 . ?
C33' H33D 0.9700 . ?
C34' C35 1.54(5) . ?
C34' H34C 0.9700 . ?
C34' H34D 0.9700 . ?
C35 C36 1.496(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
C35 H35D 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.363(3) . ?
C37 C42 1.429(3) . ?
C37 C51 1.500(3) . ?
C38 C39 1.435(3) . ?
C39 C40 1.377(3) . ?
C39 C47 1.446(3) . ?
C40 C41 1.392(3) . ?
C40 H40 0.9300 . ?
C41 C46 1.414(3) . ?
C41 C42 1.422(3) . ?
C42 C43 1.403(3) . ?
C43 C44 1.353(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.400(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.350(4) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C48 1.344(3) . ?
C47 H47 0.9300 . ?
C48 C50 1.422(4) . ?
C48 C49 1.434(4) . ?
C51 C52 1.374(3) . ?
C51 C56 1.432(3) . ?
C52 C53 1.424(3) . ?
C53 C54 1.365(3) . ?
C53 C61 1.450(3) . ?
C54 C55 1.396(3) . ?
C54 H54 0.9300 . ?
C55 C60 1.418(3) . ?
C55 C56 1.421(3) . ?
C56 C57 1.410(3) . ?
C57 C58 1.357(3) . ?
C57 H57 0.9300 . ?
C58 C59 1.394(3) . ?
C58 H58 0.9300 . ?
C59 C60 1.350(3) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
C61 C62 1.341(3) . ?
C61 H61 0.9300 . ?
C62 C64 1.427(4) . ?
C62 C63 1.429(3) . ?
C65 C66 1.509(6) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 C67 1.490(11) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?
C67 C68 1.474(15) . ?
C67 H67A 0.9700 . ?
C67 H67B 0.9700 . ?
C68 C69 1.513(13) . ?
C68 H68A 0.9700 . ?
C68 H68B 0.9700 . ?
C69 C70 1.525(15) . ?
C69 H69A 0.9700 . ?
C69 H69B 0.9700 . ?
C70 C71 1.481(8) . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C71 C72 1.50(2) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 H72A 0.9700 . ?
C72 H72B 0.9700 . ?
C65' C66' 1.52(2) . ?
C65' H65C 0.9700 . ?
C65' H65D 0.9700 . ?
C66' C67' 1.54(4) . ?
C66' H66C 0.9700 . ?
C66' H66D 0.9700 . ?
C67' C68' 1.57(4) . ?
C67' H67C 0.9700 . ?
C67' H67D 0.9700 . ?
C68' C69' 1.52(3) . ?
C68' H68C 0.9700 . ?
C68' H68D 0.9700 . ?
C69' C70' 1.54(4) . ?
C69' H69C 0.9700 . ?
C69' H69D 0.9700 . ?
C70' C71' 1.51(3) . ?
C70' H70C 0.9700 . ?
C70' H70D 0.9700 . ?
C71' C72' 1.51(7) . ?
C71' H71C 0.9700 . ?
C71' H71D 0.9700 . ?
C72' H72C 0.9700 . ?
C72' H72D 0.9700 . ?

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 O1 C29 117.45(18) . . ?
C16 O2 C36 116.01(18) . . ?
C38 O3 C65 121.4(2) . . ?
C38 O3 C65' 120.0(6) . . ?
C65 O3 C65' 50.4(7) . . ?
C52 O4 C72' 134(2) . . ?
C52 O4 C72 117.9(7) . . ?
C72' O4 C72 17(2) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C15 122.51(19) . . ?
C6 C1 C15 118.47(19) . . ?
C1 C2 O1 121.17(19) . . ?
C1 C2 C3 122.1(2) . . ?
O1 C2 C3 116.67(19) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 C11 123.4(2) . . ?
C2 C3 C11 118.6(2) . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C10 121.0(2) . . ?
C4 C5 C6 119.0(2) . . ?
C10 C5 C6 119.9(2) . . ?
C7 C6 C5 117.8(2) . . ?
C7 C6 C1 122.7(2) . . ?
C5 C6 C1 119.5(2) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C12 C11 C3 128.6(2) . . ?
C12 C11 H11 115.7 . . ?
C3 C11 H11 115.7 . . ?
C11 C12 C14 124.4(3) . . ?
C11 C12 C13 121.6(3) . . ?
C14 C12 C13 113.8(2) . . ?
N1 C13 C12 177.9(4) . . ?
N2 C14 C12 176.7(4) . . ?
C16 C15 C20 119.8(2) . . ?
C16 C15 C1 121.28(19) . . ?
C20 C15 C1 118.65(19) . . ?
O2 C16 C15 121.6(2) . . ?
O2 C16 C17 117.5(2) . . ?
C15 C16 C17 120.8(2) . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 C25 123.5(2) . . ?
C16 C17 C25 117.5(2) . . ?
C17 C18 C19 122.4(2) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C24 122.4(2) . . ?
C18 C19 C20 118.4(2) . . ?
C24 C19 C20 119.2(2) . . ?
C21 C20 C15 122.7(2) . . ?
C21 C20 C19 117.4(2) . . ?
C15 C20 C19 119.8(2) . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 121.4(2) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
C26 C25 C17 128.9(3) . . ?
C26 C25 H25 115.5 . . ?
C17 C25 H25 115.5 . . ?
C25 C26 C28 125.4(3) . . ?
C25 C26 C27 119.9(3) . . ?
C28 C26 C27 114.7(3) . . ?
N3 C27 C26 179.2(4) . . ?
N4 C28 C26 177.8(4) . . ?
O1 C29 C30 109.8(2) . . ?
O1 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
O1 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C31 C30 C29 114.9(3) . . ?
C31 C30 C31' 39.8(3) . . ?
C29 C30 C31' 122.2(3) . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30A 108.5 . . ?
C31' C30 H30A 69.3 . . ?
C31 C30 H30B 108.5 . . ?
C29 C30 H30B 108.5 . . ?
C31' C30 H30B 127.6 . . ?
H30A C30 H30B 107.5 . . ?
C31 C30 H30C 72.4 . . ?
C29 C30 H30C 106.5 . . ?
C31' C30 H30C 106.7 . . ?
H30A C30 H30C 140.0 . . ?
H30B C30 H30C 41.8 . . ?
C31 C30 H30D 136.6 . . ?
C29 C30 H30D 107.1 . . ?
C31' C30 H30D 107.0 . . ?
H30A C30 H30D 44.5 . . ?
H30B C30 H30D 66.0 . . ?
H30C C30 H30D 106.5 . . ?
C30 C31 C32 120.7(6) . . ?
C30 C31 H30C 38.9 . . ?
C32 C31 H30C 151.3 . . ?
C30 C31 H31A 107.1 . . ?
C32 C31 H31A 107.1 . . ?
H30C C31 H31A 73.1 . . ?
C30 C31 H31B 107.1 . . ?
C32 C31 H31B 107.1 . . ?
H30C C31 H31B 99.9 . . ?
H31A C31 H31B 106.8 . . ?
C31 C32 C33 115.9(9) . . ?
C31 C32 H32A 108.3 . . ?
C33 C32 H32A 108.3 . . ?
C31 C32 H32B 108.3 . . ?
C33 C32 H32B 108.3 . . ?
H32A C32 H32B 107.4 . . ?
C32 C33 C34 119.2(14) . . ?
C32 C33 H33A 107.5 . . ?
C34 C33 H33A 107.5 . . ?
C32 C33 H33B 107.5 . . ?
C34 C33 H33B 107.5 . . ?
H33A C33 H33B 107.0 . . ?
C33 C34 C35 110(2) . . ?
C33 C34 H34A 109.7 . . ?
C35 C34 H34A 109.7 . . ?
C33 C34 H34B 109.7 . . ?
C35 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
C32' C31' C30 122.2(11) . . ?
C32' C31' H31C 106.8 . . ?
C30 C31' H31C 106.8 . . ?
C32' C31' H31D 106.8 . . ?
C30 C31' H31D 106.8 . . ?
H31C C31' H31D 106.6 . . ?
C31' C32' C33' 115.8(17) . . ?
C31' C32' H32C 108.3 . . ?
C33' C32' H32C 108.3 . . ?
C31' C32' H32D 108.3 . . ?
C33' C32' H32D 108.3 . . ?
H32C C32' H32D 107.4 . . ?
C34' C33' C32' 116(2) . . ?
C34' C33' H33C 108.2 . . ?
C32' C33' H33C 108.2 . . ?
C34' C33' H33D 108.2 . . ?
C32' C33' H33D 108.2 . . ?
H33C C33' H33D 107.4 . . ?
C33' C34' C35 122(3) . . ?
C33' C34' H34C 106.8 . . ?
C35 C34' H34C 106.8 . . ?
C33' C34' H34D 106.8 . . ?
C35 C34' H34D 106.8 . . ?
H34C C34' H34D 106.6 . . ?
C36 C35 C34 111.1(12) . . ?
C36 C35 C34' 117.1(17) . . ?
C34 C35 C34' 11(3) . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35A 109.4 . . ?
C34' C35 H35A 113.1 . . ?
C36 C35 H35B 109.4 . . ?
C34 C35 H35B 109.4 . . ?
C34' C35 H35B 98.9 . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 H35C 107.3 . . ?
C34 C35 H35C 103.3 . . ?
C34' C35 H35C 108.2 . . ?
H35A C35 H35C 8.4 . . ?
H35B C35 H35C 116.1 . . ?
C36 C35 H35D 108.1 . . ?
C34 C35 H35D 119.2 . . ?
C34' C35 H35D 108.6 . . ?
H35A C35 H35D 98.7 . . ?
H35B C35 H35D 11.1 . . ?
H35C C35 H35D 106.9 . . ?
O2 C36 C35 113.7(2) . . ?
O2 C36 H36A 108.8 . . ?
C35 C36 H36A 108.8 . . ?
O2 C36 H36B 108.8 . . ?
C35 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
C38 C37 C42 119.5(2) . . ?
C38 C37 C51 121.4(2) . . ?
C42 C37 C51 119.0(2) . . ?
C37 C38 O3 121.7(2) . . ?
C37 C38 C39 122.1(2) . . ?
O3 C38 C39 115.9(2) . . ?
C40 C39 C38 117.6(2) . . ?
C40 C39 C47 123.6(2) . . ?
C38 C39 C47 118.8(2) . . ?
C39 C40 C41 122.5(2) . . ?
C39 C40 H40 118.7 . . ?
C41 C40 H40 118.7 . . ?
C40 C41 C46 121.5(2) . . ?
C40 C41 C42 119.3(2) . . ?
C46 C41 C42 119.2(2) . . ?
C43 C42 C41 117.6(2) . . ?
C43 C42 C37 123.4(2) . . ?
C41 C42 C37 119.0(2) . . ?
C44 C43 C42 121.5(2) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 121.1(3) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C46 C45 C44 119.4(3) . . ?
C46 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
C45 C46 C41 121.2(2) . . ?
C45 C46 H46 119.4 . . ?
C41 C46 H46 119.4 . . ?
C48 C47 C39 129.8(3) . . ?
C48 C47 H47 115.1 . . ?
C39 C47 H47 115.1 . . ?
C47 C48 C50 120.6(3) . . ?
C47 C48 C49 126.5(3) . . ?
C50 C48 C49 112.9(2) . . ?
N5 C49 C48 177.1(3) . . ?
N6 C50 C48 177.6(4) . . ?
C52 C51 C56 118.94(19) . . ?
C52 C51 C37 122.2(2) . . ?
C56 C51 C37 118.75(18) . . ?
O4 C52 C51 122.3(2) . . ?
O4 C52 C53 115.76(19) . . ?
C51 C52 C53 121.7(2) . . ?
C54 C53 C52 118.6(2) . . ?
C54 C53 C61 122.3(2) . . ?
C52 C53 C61 118.9(2) . . ?
C53 C54 C55 122.2(2) . . ?
C53 C54 H54 118.9 . . ?
C55 C54 H54 118.9 . . ?
C54 C55 C60 121.6(2) . . ?
C54 C55 C56 119.1(2) . . ?
C60 C55 C56 119.2(2) . . ?
C57 C56 C55 117.5(2) . . ?
C57 C56 C51 123.19(19) . . ?
C55 C56 C51 119.25(19) . . ?
C58 C57 C56 121.4(2) . . ?
C58 C57 H57 119.3 . . ?
C56 C57 H57 119.3 . . ?
C57 C58 C59 120.9(2) . . ?
C57 C58 H58 119.5 . . ?
C59 C58 H58 119.5 . . ?
C60 C59 C58 119.9(2) . . ?
C60 C59 H59 120.1 . . ?
C58 C59 H59 120.1 . . ?
C59 C60 C55 121.0(2) . . ?
C59 C60 H60 119.5 . . ?
C55 C60 H60 119.5 . . ?
C62 C61 C53 128.5(2) . . ?
C62 C61 H61 115.8 . . ?
C53 C61 H61 115.8 . . ?
C61 C62 C64 124.6(2) . . ?
C61 C62 C63 120.2(2) . . ?
C64 C62 C63 115.1(2) . . ?
N7 C63 C62 178.3(3) . . ?
N8 C64 C62 177.7(3) . . ?
O3 C65 C66 108.3(3) . . ?
O3 C65 H65A 110.0 . . ?
C66 C65 H65A 110.0 . . ?
O3 C65 H65B 110.0 . . ?
C66 C65 H65B 110.0 . . ?
H65A C65 H65B 108.4 . . ?
C67 C66 C65 115.9(5) . . ?
C67 C66 H66A 108.3 . . ?
C65 C66 H66A 108.3 . . ?
C67 C66 H66B 108.3 . . ?
C65 C66 H66B 108.3 . . ?
H66A C66 H66B 107.4 . . ?
C68 C67 C66 111.5(8) . . ?
C68 C67 H67A 109.3 . . ?
C66 C67 H67A 109.3 . . ?
C68 C67 H67B 109.3 . . ?
C66 C67 H67B 109.3 . . ?
H67A C67 H67B 108.0 . . ?
C67 C68 C69 113.3(9) . . ?
C67 C68 H68A 108.9 . . ?
C69 C68 H68A 108.9 . . ?
C67 C68 H68B 108.9 . . ?
C69 C68 H68B 108.9 . . ?
H68A C68 H68B 107.7 . . ?
C68 C69 C70 107.2(9) . . ?
C68 C69 H69A 110.3 . . ?
C70 C69 H69A 110.3 . . ?
C68 C69 H69B 110.3 . . ?
C70 C69 H69B 110.3 . . ?
H69A C69 H69B 108.5 . . ?
C71 C70 C69 117.3(6) . . ?
C71 C70 H70A 108.0 . . ?
C69 C70 H70A 108.0 . . ?
C71 C70 H70B 108.0 . . ?
C69 C70 H70B 108.0 . . ?
H70A C70 H70B 107.2 . . ?
C70 C71 C72 114.2(11) . . ?
C70 C71 H71A 108.7 . . ?
C72 C71 H71A 108.7 . . ?
C70 C71 H71B 108.7 . . ?
C72 C71 H71B 108.7 . . ?
H71A C71 H71B 107.6 . . ?
O4 C72 C71 103.6(15) . . ?
O4 C72 H72A 111.0 . . ?
C71 C72 H72A 111.0 . . ?
O4 C72 H72B 111.0 . . ?
C71 C72 H72B 111.0 . . ?
H72A C72 H72B 109.0 . . ?
O3 C65' C66' 120.8(12) . . ?
O3 C65' H65C 107.1 . . ?
C66' C65' H65C 107.1 . . ?
O3 C65' H65D 107.1 . . ?
C66' C65' H65D 107.1 . . ?
H65C C65' H65D 106.8 . . ?
C65' C66' C67' 119.3(16) . . ?
C65' C66' H66C 107.5 . . ?
C67' C66' H66C 107.5 . . ?
C65' C66' H66D 107.5 . . ?
C67' C66' H66D 107.5 . . ?
H66C C66' H66D 107.0 . . ?
C66' C67' C68' 133(2) . . ?
C66' C67' H67C 103.9 . . ?
C68' C67' H67C 103.9 . . ?
C66' C67' H67D 103.9 . . ?
C68' C67' H67D 103.9 . . ?
H67C C67' H67D 105.4 . . ?
C69' C68' C67' 100(2) . . ?
C69' C68' H68C 111.8 . . ?
C67' C68' H68C 111.8 . . ?
C69' C68' H68D 111.8 . . ?
C67' C68' H68D 111.8 . . ?
H68C C68' H68D 109.5 . . ?
C68' C69' C70' 99(2) . . ?
C68' C69' H69C 112.0 . . ?
C70' C69' H69C 112.0 . . ?
C68' C69' H69D 112.0 . . ?
C70' C69' H69D 112.0 . . ?
H69C C69' H69D 109.7 . . ?
C71' C70' C69' 121(3) . . ?
C71' C70' H70C 107.1 . . ?
C69' C70' H70C 107.1 . . ?
C71' C70' H70D 107.1 . . ?
C69' C70' H70D 107.1 . . ?
H70C C70' H70D 106.8 . . ?
C72' C71' C70' 138(3) . . ?
C72' C71' H71C 102.5 . . ?
C70' C71' H71C 102.5 . . ?
C72' C71' H71D 102.5 . . ?
C70' C71' H71D 102.5 . . ?
H71C C71' H71D 104.9 . . ?
O4 C72' C71' 141(5) . . ?
O4 C72' H72C 101.8 . . ?
C71' C72' H72C 101.8 . . ?
O4 C72' H72D 101.8 . . ?
C71' C72' H72D 101.8 . . ?
H72C C72' H72D 104.7 . . ?

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 O1 177.55(18) . . . . ?
C15 C1 C2 O1 1.1(3) . . . . ?
C6 C1 C2 C3 -6.2(3) . . . . ?
C15 C1 C2 C3 177.4(2) . . . . ?
C29 O1 C2 C1 -90.0(3) . . . . ?
C29 O1 C2 C3 93.5(3) . . . . ?
C1 C2 C3 C4 3.7(3) . . . . ?
O1 C2 C3 C4 -179.89(18) . . . . ?
C1 C2 C3 C11 -174.1(2) . . . . ?
O1 C2 C3 C11 2.3(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C11 C3 C4 C5 179.3(2) . . . . ?
C3 C4 C5 C10 174.2(2) . . . . ?
C3 C4 C5 C6 -4.0(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C10 C5 C6 C1 -176.9(2) . . . . ?
C2 C1 C6 C7 -173.3(2) . . . . ?
C15 C1 C6 C7 3.2(3) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
C15 C1 C6 C5 -179.87(19) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C1 C6 C7 C8 175.5(2) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C9 C10 C5 -1.6(4) . . . . ?
C4 C5 C10 C9 -176.9(2) . . . . ?
C6 C5 C10 C9 1.3(4) . . . . ?
C4 C3 C11 C12 26.4(4) . . . . ?
C2 C3 C11 C12 -155.9(2) . . . . ?
C3 C11 C12 C14 4.4(4) . . . . ?
C3 C11 C12 C13 178.6(3) . . . . ?
C11 C12 C13 N1 -150(9) . . . . ?
C14 C12 C13 N1 25(9) . . . . ?
C11 C12 C14 N2 141(7) . . . . ?
C13 C12 C14 N2 -33(7) . . . . ?
C2 C1 C15 C16 -89.8(3) . . . . ?
C6 C1 C15 C16 93.7(3) . . . . ?
C2 C1 C15 C20 96.2(3) . . . . ?
C6 C1 C15 C20 -80.2(3) . . . . ?
C36 O2 C16 C15 80.0(3) . . . . ?
C36 O2 C16 C17 -104.2(2) . . . . ?
C20 C15 C16 O2 177.0(2) . . . . ?
C1 C15 C16 O2 3.1(3) . . . . ?
C20 C15 C16 C17 1.3(3) . . . . ?
C1 C15 C16 C17 -172.6(2) . . . . ?
O2 C16 C17 C18 -176.4(2) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
O2 C16 C17 C25 -0.2(3) . . . . ?
C15 C16 C17 C25 175.6(2) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C25 C17 C18 C19 -176.7(2) . . . . ?
C17 C18 C19 C24 -179.8(2) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C16 C15 C20 C21 -179.4(2) . . . . ?
C1 C15 C20 C21 -5.4(3) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C1 C15 C20 C19 173.2(2) . . . . ?
C18 C19 C20 C21 178.2(2) . . . . ?
C24 C19 C20 C21 -0.8(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C24 C19 C20 C15 -179.4(2) . . . . ?
C15 C20 C21 C22 179.4(2) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C19 0.4(4) . . . . ?
C18 C19 C24 C23 -178.8(3) . . . . ?
C20 C19 C24 C23 0.2(4) . . . . ?
C18 C17 C25 C26 -20.8(4) . . . . ?
C16 C17 C25 C26 163.3(3) . . . . ?
C17 C25 C26 C28 -4.4(5) . . . . ?
C17 C25 C26 C27 176.2(3) . . . . ?
C25 C26 C27 N3 -119(42) . . . . ?
C28 C26 C27 N3 62(42) . . . . ?
C25 C26 C28 N4 -159(12) . . . . ?
C27 C26 C28 N4 20(12) . . . . ?
C2 O1 C29 C30 -160.7(2) . . . . ?
O1 C29 C30 C31 -78.6(4) . . . . ?
O1 C29 C30 C31' -33.7(6) . . . . ?
C29 C30 C31 C32 52.2(9) . . . . ?
C31' C30 C31 C32 -59.0(8) . . . . ?
C30 C31 C32 C33 59.0(11) . . . . ?
C31 C32 C33 C34 178.8(16) . . . . ?
C32 C33 C34 C35 45(2) . . . . ?
C31 C30 C31' C32' 31.6(11) . . . . ?
C29 C30 C31' C32' -59.6(13) . . . . ?
C30 C31' C32' C33' 155.9(9) . . . . ?
C31' C32' C33' C34' -71(2) . . . . ?
C32' C33' C34' C35 -66(4) . . . . ?
C33 C34 C35 C36 73(2) . . . . ?
C33 C34 C35 C34' -53(16) . . . . ?
C33' C34' C35 C36 123(3) . . . . ?
C33' C34' C35 C34 -180(20) . . . . ?
C16 O2 C36 C35 65.6(3) . . . . ?
C34 C35 C36 O2 -170.4(14) . . . . ?
C34' C35 C36 O2 -161(2) . . . . ?
C42 C37 C38 O3 172.5(2) . . . . ?
C51 C37 C38 O3 -3.7(3) . . . . ?
C42 C37 C38 C39 -0.9(3) . . . . ?
C51 C37 C38 C39 -177.0(2) . . . . ?
C65 O3 C38 C37 67.4(3) . . . . ?
C65' O3 C38 C37 126.7(8) . . . . ?
C65 O3 C38 C39 -118.9(3) . . . . ?
C65' O3 C38 C39 -59.5(8) . . . . ?
C37 C38 C39 C40 1.0(3) . . . . ?
O3 C38 C39 C40 -172.7(2) . . . . ?
C37 C38 C39 C47 178.7(2) . . . . ?
O3 C38 C39 C47 4.9(3) . . . . ?
C38 C39 C40 C41 -0.1(3) . . . . ?
C47 C39 C40 C41 -177.7(2) . . . . ?
C39 C40 C41 C46 176.9(2) . . . . ?
C39 C40 C41 C42 -0.8(4) . . . . ?
C40 C41 C42 C43 179.1(2) . . . . ?
C46 C41 C42 C43 1.3(3) . . . . ?
C40 C41 C42 C37 0.9(3) . . . . ?
C46 C41 C42 C37 -176.8(2) . . . . ?
C38 C37 C42 C43 -178.1(2) . . . . ?
C51 C37 C42 C43 -1.9(3) . . . . ?
C38 C37 C42 C41 -0.1(3) . . . . ?
C51 C37 C42 C41 176.1(2) . . . . ?
C41 C42 C43 C44 -1.0(4) . . . . ?
C37 C42 C43 C44 177.1(2) . . . . ?
C42 C43 C44 C45 -0.1(4) . . . . ?
C43 C44 C45 C46 0.9(5) . . . . ?
C44 C45 C46 C41 -0.4(4) . . . . ?
C40 C41 C46 C45 -178.3(3) . . . . ?
C42 C41 C46 C45 -0.7(4) . . . . ?
C40 C39 C47 C48 -15.4(4) . . . . ?
C38 C39 C47 C48 167.1(3) . . . . ?
C39 C47 C48 C50 177.4(3) . . . . ?
C39 C47 C48 C49 -0.6(5) . . . . ?
C47 C48 C49 N5 155(7) . . . . ?
C50 C48 C49 N5 -24(7) . . . . ?
C47 C48 C50 N6 -149(10) . . . . ?
C49 C48 C50 N6 30(11) . . . . ?
C38 C37 C51 C52 -116.8(3) . . . . ?
C42 C37 C51 C52 67.1(3) . . . . ?
C38 C37 C51 C56 66.5(3) . . . . ?
C42 C37 C51 C56 -109.7(2) . . . . ?
C72' O4 C52 C51 64(4) . . . . ?
C72 O4 C52 C51 68.8(10) . . . . ?
C72' O4 C52 C53 -121(4) . . . . ?
C72 O4 C52 C53 -116.8(10) . . . . ?
C56 C51 C52 O4 170.6(2) . . . . ?
C37 C51 C52 O4 -6.1(4) . . . . ?
C56 C51 C52 C53 -3.5(3) . . . . ?
C37 C51 C52 C53 179.8(2) . . . . ?
O4 C52 C53 C54 -171.8(2) . . . . ?
C51 C52 C53 C54 2.8(3) . . . . ?
O4 C52 C53 C61 4.1(3) . . . . ?
C51 C52 C53 C61 178.6(2) . . . . ?
C52 C53 C54 C55 0.4(3) . . . . ?
C61 C53 C54 C55 -175.3(2) . . . . ?
C53 C54 C55 C60 176.4(2) . . . . ?
C53 C54 C55 C56 -2.6(3) . . . . ?
C54 C55 C56 C57 178.56(19) . . . . ?
C60 C55 C56 C57 -0.4(3) . . . . ?
C54 C55 C56 C51 1.7(3) . . . . ?
C60 C55 C56 C51 -177.3(2) . . . . ?
C52 C51 C56 C57 -175.4(2) . . . . ?
C37 C51 C56 C57 1.4(3) . . . . ?
C52 C51 C56 C55 1.2(3) . . . . ?
C37 C51 C56 C55 178.09(19) . . . . ?
C55 C56 C57 C58 0.6(3) . . . . ?
C51 C56 C57 C58 177.3(2) . . . . ?
C56 C57 C58 C59 -0.5(4) . . . . ?
C57 C58 C59 C60 0.2(4) . . . . ?
C58 C59 C60 C55 0.0(4) . . . . ?
C54 C55 C60 C59 -178.8(2) . . . . ?
C56 C55 C60 C59 0.2(3) . . . . ?
C54 C53 C61 C62 -27.8(4) . . . . ?
C52 C53 C61 C62 156.5(2) . . . . ?
C53 C61 C62 C64 -6.2(4) . . . . ?
C53 C61 C62 C63 175.4(2) . . . . ?
C61 C62 C63 N7 -83(10) . . . . ?
C64 C62 C63 N7 98(10) . . . . ?
C61 C62 C64 N8 -126(7) . . . . ?
C63 C62 C64 N8 53(7) . . . . ?
C38 O3 C65 C66 71.0(4) . . . . ?
C65' O3 C65 C66 -33.9(9) . . . . ?
O3 C65 C66 C67 177.1(7) . . . . ?
C65 C66 C67 C68 74.5(11) . . . . ?
C66 C67 C68 C69 72.5(11) . . . . ?
C67 C68 C69 C70 -162.7(7) . . . . ?
C68 C69 C70 C71 58.6(11) . . . . ?
C69 C70 C71 C72 47.5(12) . . . . ?
C52 O4 C72 C71 96.4(9) . . . . ?
C72' O4 C72 C71 -95(13) . . . . ?
C70 C71 C72 O4 178.5(7) . . . . ?
C38 O3 C65' C66' -121.9(12) . . . . ?
C65 O3 C65' C66' -14.3(10) . . . . ?
O3 C65' C66' C67' 94(2) . . . . ?
C65' C66' C67' C68' 61(3) . . . . ?
C66' C67' C68' C69' -168(3) . . . . ?
C67' C68' C69' C70' 108(2) . . . . ?
C68' C69' C70' C71' -119(3) . . . . ?
C69' C70' C71' C72' 91(5) . . . . ?
C52 O4 C72' C71' 85(7) . . . . ?
C72 O4 C72' C71' 71(11) . . . . ?
C70' C71' C72' O4 -116(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.264
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1823471'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H22 Cl2 N4 O2'
_chemical_formula_weight         577.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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)

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

_cell_length_a                   7.9714(4)
_cell_length_b                   22.5703(8)
_cell_length_c                   9.1047(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.426(7)
_cell_angle_gamma                90.00
_cell_volume                     1479.42(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3784
_cell_measurement_theta_min      5.3690
_cell_measurement_theta_max      71.5160

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_T_max  0.4877
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0356
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7545
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         66.04
_reflns_number_total             3791
_reflns_number_gt                3566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1226P)²+0.3157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     371
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.062
_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
Cl1 Cl 0.2819(4) 0.36383(17) 0.2417(6) 0.235(2) Uani 1 1 d D . .
Cl2 Cl 0.1994(5) 0.48087(15) 0.1064(7) 0.242(2) Uani 1 1 d D . .
N1 N 0.8411(9) 0.4028(3) 0.7692(6) 0.109(2) Uani 1 1 d . . .
N2 N 0.8034(10) 0.3458(2) 0.3161(6) 0.1090(19) Uani 1 1 d . . .
N3 N 0.3652(8) 0.94791(19) -0.0219(5) 0.0827(13) Uani 1 1 d . . .
N4 N 0.8328(8) 0.9897(2) 0.4131(10) 0.139(3) Uani 1 1 d . . .
O1 O 0.6567(3) 0.59024(11) 0.2359(2) 0.0404(5) Uani 1 1 d . . .
O2 O 0.7767(3) 0.74390(12) 0.4578(3) 0.0446(6) Uani 1 1 d . . .
C1 C 0.5548(4) 0.64231(15) 0.4072(4) 0.0331(7) Uani 1 1 d . . .
C2 C 0.6212(4) 0.59171(15) 0.3705(4) 0.0356(7) Uani 1 1 d . . .
C3 C 0.6485(5) 0.53910(15) 0.4664(4) 0.0386(7) Uani 1 1 d . . .
C4 C 0.6230(5) 0.54209(16) 0.6046(4) 0.0430(8) Uani 1 1 d . . .
H4 H 0.6444 0.5083 0.6687 0.052 Uiso 1 1 calc R . .
C5 C 0.5656(5) 0.59424(16) 0.6543(4) 0.0389(7) Uani 1 1 d . . .
C6 C 0.5250(4) 0.64520(15) 0.5517(4) 0.0355(7) Uani 1 1 d . . .
C7 C 0.4613(5) 0.69666(17) 0.6000(4) 0.0429(8) Uani 1 1 d . . .
H7 H 0.4318 0.7302 0.5343 0.051 Uiso 1 1 calc R . .
C8 C 0.4426(5) 0.6977(2) 0.7424(4) 0.0539(10) Uani 1 1 d . . .
H8 H 0.4017 0.7322 0.7727 0.065 Uiso 1 1 calc R . .
C9 C 0.4840(6) 0.6478(2) 0.8433(5) 0.0591(11) Uani 1 1 d . . .
H9 H 0.4712 0.6494 0.9401 0.071 Uiso 1 1 calc R . .
C10 C 0.5425(6) 0.59728(18) 0.8002(4) 0.0482(9) Uani 1 1 d . . .
H10 H 0.5679 0.5641 0.8670 0.058 Uiso 1 1 calc R . .
C11 C 0.6876(5) 0.48458(16) 0.4018(4) 0.0434(8) Uani 1 1 d . . .
H11 H 0.6657 0.4864 0.2930 0.052 Uiso 1 1 calc R . .
C12 C 0.7502(6) 0.43193(17) 0.4736(4) 0.0488(9) Uani 1 1 d . . .
C13 C 0.8025(7) 0.4177(2) 0.6396(5) 0.0666(12) Uani 1 1 d . . .
C14 C 0.7776(8) 0.38452(19) 0.3831(5) 0.0653(12) Uani 1 1 d . . .
C15 C 0.4981(4) 0.69444(15) 0.2941(3) 0.0339(7) Uani 1 1 d . . .
C16 C 0.6052(5) 0.74447(16) 0.3291(4) 0.0374(7) Uani 1 1 d . . .
C17 C 0.5365(5) 0.79821(16) 0.2364(4) 0.0411(8) Uani 1 1 d . . .
C18 C 0.3684(5) 0.79623(17) 0.1006(4) 0.0444(8) Uani 1 1 d . . .
H18 H 0.3238 0.8304 0.0389 0.053 Uiso 1 1 calc R . .
C19 C 0.2621(4) 0.74364(16) 0.0527(4) 0.0391(7) Uani 1 1 d . . .
C20 C 0.3258(4) 0.69253(15) 0.1527(3) 0.0336(7) Uani 1 1 d . . .
C21 C 0.2154(5) 0.64083(17) 0.1037(4) 0.0417(8) Uani 1 1 d . . .
H21 H 0.2513 0.6071 0.1686 0.050 Uiso 1 1 calc R . .
C22 C 0.0557(5) 0.63986(19) -0.0386(5) 0.0506(9) Uani 1 1 d . . .
H22 H -0.0134 0.6052 -0.0709 0.061 Uiso 1 1 calc R . .
C23 C -0.0036(5) 0.6904(2) -0.1349(5) 0.0577(11) Uani 1 1 d . . .
H23 H -0.1130 0.6892 -0.2303 0.069 Uiso 1 1 calc R . .
C24 C 0.0955(5) 0.74113(19) -0.0917(4) 0.0502(9) Uani 1 1 d . . .
H24 H 0.0539 0.7745 -0.1572 0.060 Uiso 1 1 calc R . .
C25 C 0.6410(5) 0.85197(17) 0.3015(5) 0.0523(9) Uani 1 1 d . . .
H25 H 0.7428 0.8470 0.4016 0.063 Uiso 1 1 calc R . .
C26 C 0.6187(6) 0.90679(18) 0.2452(5) 0.0549(10) Uani 1 1 d . . .
C27 C 0.4771(7) 0.92764(18) 0.0941(5) 0.0565(10) Uani 1 1 d . . .
C28 C 0.7395(7) 0.9531(2) 0.3394(7) 0.0767(15) Uani 1 1 d . . .
C29 C 0.8531(5) 0.58598(18) 0.2727(4) 0.0488(9) Uani 1 1 d . . .
H29A H 0.8664 0.5868 0.1717 0.059 Uiso 1 1 calc R . .
H29B H 0.9005 0.5482 0.3252 0.059 Uiso 1 1 calc R . .
C30 C 0.9679(5) 0.63487(18) 0.3808(5) 0.0527(9) Uani 1 1 d . . .
H30A H 1.0982 0.6257 0.4145 0.063 Uiso 1 1 calc R . .
H30B H 0.9463 0.6360 0.4778 0.063 Uiso 1 1 calc R . .
C31 C 0.9280(5) 0.6960(2) 0.3021(5) 0.0533(9) Uani 1 1 d . . .
H31A H 1.0198 0.7045 0.2615 0.064 Uiso 1 1 calc R . .
H31B H 0.8073 0.6951 0.2094 0.064 Uiso 1 1 calc R . .
C32 C 0.9293(5) 0.7458(2) 0.4126(5) 0.0561(10) Uani 1 1 d . . .
H32A H 1.0450 0.7444 0.5106 0.067 Uiso 1 1 calc R . .
H32B H 0.9254 0.7832 0.3588 0.067 Uiso 1 1 calc R . .
C33 C 0.1202(11) 0.4180(4) 0.1629(11) 0.141(3) Uani 1 1 d D . .
H33A H 0.0754 0.4287 0.2430 0.170 Uiso 1 1 calc R . .
H33B H 0.0157 0.4024 0.0686 0.170 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
Cl1 C33 1.696(7) . ?
Cl2 C33 1.719(7) . ?
N1 C13 1.135(6) . ?
N2 C14 1.134(6) . ?
N3 C27 1.146(6) . ?
N4 C28 1.121(7) . ?
O1 C2 1.372(3) . ?
O1 C29 1.457(4) . ?
O2 C16 1.366(4) . ?
O2 C32 1.442(5) . ?
C1 C2 1.359(5) . ?
C1 C6 1.435(4) . ?
C1 C15 1.500(4) . ?
C2 C3 1.434(5) . ?
C3 C4 1.359(5) . ?
C3 C11 1.454(5) . ?
C4 C5 1.406(5) . ?
C4 H4 0.9300 . ?
C5 C10 1.420(4) . ?
C5 C6 1.428(5) . ?
C6 C7 1.411(5) . ?
C7 C8 1.368(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.345(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.421(6) . ?
C12 C14 1.423(6) . ?
C15 C16 1.368(5) . ?
C15 C20 1.424(4) . ?
C16 C17 1.445(5) . ?
C17 C18 1.380(5) . ?
C17 C25 1.447(5) . ?
C18 C19 1.414(5) . ?
C18 H18 0.9300 . ?
C19 C24 1.413(5) . ?
C19 C20 1.421(5) . ?
C20 C21 1.414(5) . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.392(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.350(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.322(6) . ?
C25 H25 0.9300 . ?
C26 C28 1.431(6) . ?
C26 C27 1.433(6) . ?
C29 C30 1.500(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.525(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.505(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

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 O1 C29 114.2(2) . . ?
C16 O2 C32 114.3(3) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C15 121.7(3) . . ?
C6 C1 C15 118.3(3) . . ?
C1 C2 O1 119.4(3) . . ?
C1 C2 C3 121.3(3) . . ?
O1 C2 C3 119.2(3) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 C11 124.0(3) . . ?
C2 C3 C11 117.2(3) . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C10 122.2(3) . . ?
C4 C5 C6 118.5(3) . . ?
C10 C5 C6 119.3(3) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 C1 123.1(3) . . ?
C5 C6 C1 118.8(3) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C3 130.6(3) . . ?
C12 C11 H11 114.7 . . ?
C3 C11 H11 114.7 . . ?
C11 C12 C13 126.5(4) . . ?
C11 C12 C14 120.0(3) . . ?
C13 C12 C14 113.4(3) . . ?
N1 C13 C12 175.7(6) . . ?
N2 C14 C12 177.6(5) . . ?
C16 C15 C20 119.9(3) . . ?
C16 C15 C1 120.9(3) . . ?
C20 C15 C1 119.1(3) . . ?
O2 C16 C15 119.1(3) . . ?
O2 C16 C17 119.9(3) . . ?
C15 C16 C17 121.0(3) . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 C25 124.2(3) . . ?
C16 C17 C25 117.2(3) . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C24 C19 C18 121.3(3) . . ?
C24 C19 C20 119.9(3) . . ?
C18 C19 C20 118.8(3) . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 C15 122.6(3) . . ?
C19 C20 C15 119.7(3) . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.5(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C26 C25 C17 131.9(4) . . ?
C26 C25 H25 114.1 . . ?
C17 C25 H25 114.1 . . ?
C25 C26 C28 120.5(4) . . ?
C25 C26 C27 126.8(4) . . ?
C28 C26 C27 112.7(4) . . ?
N3 C27 C26 175.5(5) . . ?
N4 C28 C26 179.4(6) . . ?
O1 C29 C30 113.3(3) . . ?
O1 C29 H29A 108.9 . . ?
C30 C29 H29A 108.9 . . ?
O1 C29 H29B 108.9 . . ?
C30 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 C31 114.3(3) . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C31 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C32 C31 C30 114.9(3) . . ?
C32 C31 H31A 108.5 . . ?
C30 C31 H31A 108.5 . . ?
C32 C31 H31B 108.5 . . ?
C30 C31 H31B 108.5 . . ?
H31A C31 H31B 107.5 . . ?
O2 C32 C31 113.9(3) . . ?
O2 C32 H32A 108.8 . . ?
C31 C32 H32A 108.8 . . ?
O2 C32 H32B 108.8 . . ?
C31 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
Cl1 C33 Cl2 114.3(5) . . ?
Cl1 C33 H33A 108.7 . . ?
Cl2 C33 H33A 108.7 . . ?
Cl1 C33 H33B 108.7 . . ?
Cl2 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -177.2(3) . . . . ?
C15 C1 C2 O1 7.3(5) . . . . ?
C6 C1 C2 C3 5.1(5) . . . . ?
C15 C1 C2 C3 -170.4(3) . . . . ?
C29 O1 C2 C1 111.5(3) . . . . ?
C29 O1 C2 C3 -70.8(4) . . . . ?
C1 C2 C3 C4 -6.0(5) . . . . ?
O1 C2 C3 C4 176.3(3) . . . . ?
C1 C2 C3 C11 169.2(3) . . . . ?
O1 C2 C3 C11 -8.5(4) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C11 C3 C4 C5 -172.9(3) . . . . ?
C3 C4 C5 C10 -178.9(3) . . . . ?
C3 C4 C5 C6 2.7(5) . . . . ?
C4 C5 C6 C7 177.9(3) . . . . ?
C10 C5 C6 C7 -0.6(5) . . . . ?
C4 C5 C6 C1 -3.7(5) . . . . ?
C10 C5 C6 C1 177.9(3) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
C15 C1 C6 C7 -6.1(5) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C15 C1 C6 C5 175.4(3) . . . . ?
C5 C6 C7 C8 1.1(5) . . . . ?
C1 C6 C7 C8 -177.3(3) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C8 C9 C10 C5 1.0(6) . . . . ?
C4 C5 C10 C9 -178.8(4) . . . . ?
C6 C5 C10 C9 -0.5(5) . . . . ?
C4 C3 C11 C12 -18.2(6) . . . . ?
C2 C3 C11 C12 166.9(4) . . . . ?
C3 C11 C12 C13 -3.0(7) . . . . ?
C3 C11 C12 C14 179.9(4) . . . . ?
C11 C12 C13 N1 151(8) . . . . ?
C14 C12 C13 N1 -31(8) . . . . ?
C11 C12 C14 N2 160(15) . . . . ?
C13 C12 C14 N2 -17(16) . . . . ?
C2 C1 C15 C16 -106.8(4) . . . . ?
C6 C1 C15 C16 77.6(4) . . . . ?
C2 C1 C15 C20 76.2(4) . . . . ?
C6 C1 C15 C20 -99.4(3) . . . . ?
C32 O2 C16 C15 110.3(4) . . . . ?
C32 O2 C16 C17 -72.2(4) . . . . ?
C20 C15 C16 O2 -174.7(3) . . . . ?
C1 C15 C16 O2 8.3(4) . . . . ?
C20 C15 C16 C17 7.8(4) . . . . ?
C1 C15 C16 C17 -169.2(3) . . . . ?
O2 C16 C17 C18 175.6(3) . . . . ?
C15 C16 C17 C18 -6.9(5) . . . . ?
O2 C16 C17 C25 -10.1(5) . . . . ?
C15 C16 C17 C25 167.4(3) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C25 C17 C18 C19 -172.8(3) . . . . ?
C17 C18 C19 C24 -176.3(3) . . . . ?
C17 C18 C19 C20 3.6(5) . . . . ?
C24 C19 C20 C21 -1.3(4) . . . . ?
C18 C19 C20 C21 178.9(3) . . . . ?
C24 C19 C20 C15 177.1(3) . . . . ?
C18 C19 C20 C15 -2.7(4) . . . . ?
C16 C15 C20 C21 175.4(3) . . . . ?
C1 C15 C20 C21 -7.6(4) . . . . ?
C16 C15 C20 C19 -2.9(4) . . . . ?
C1 C15 C20 C19 174.1(3) . . . . ?
C19 C20 C21 C22 2.2(4) . . . . ?
C15 C20 C21 C22 -176.1(3) . . . . ?
C20 C21 C22 C23 -2.0(5) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C22 C23 C24 C19 0.1(6) . . . . ?
C18 C19 C24 C23 180.0(4) . . . . ?
C20 C19 C24 C23 0.1(5) . . . . ?
C18 C17 C25 C26 -8.4(7) . . . . ?
C16 C17 C25 C26 177.7(4) . . . . ?
C17 C25 C26 C28 177.0(4) . . . . ?
C17 C25 C26 C27 -1.0(8) . . . . ?
C25 C26 C27 N3 153(6) . . . . ?
C28 C26 C27 N3 -25(6) . . . . ?
C25 C26 C28 N4 -127(82) . . . . ?
C27 C26 C28 N4 51(82) . . . . ?
C2 O1 C29 C30 -56.4(4) . . . . ?
O1 C29 C30 C31 -67.7(4) . . . . ?
C29 C30 C31 C32 140.9(3) . . . . ?
C16 O2 C32 C31 -57.4(5) . . . . ?
C30 C31 C32 O2 -68.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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 1823473'
_audit_update_record             
;
2018-02-11 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H30 F6 N4 O2'
_chemical_formula_weight         808.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   18.4373(19)
_cell_length_b                   25.7446(19)
_cell_length_c                   11.6266(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5518.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3931
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      62.11

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8251
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21542
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         66.03
_reflns_number_total             4819
_reflns_number_gt                2819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0972P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(5)
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.2375
_refine_ls_wR_factor_gt          0.2191
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
F1 F -0.1551(4) 0.6315(2) -0.3235(5) 0.204(3) Uani 1 1 d . . .
F2 F -0.2121(5) 0.6250(3) -0.1722(6) 0.221(3) Uani 1 1 d . . .
F3 F -0.1065(5) 0.5943(3) -0.1784(8) 0.232(4) Uani 1 1 d . . .
N1 N 0.2264(3) 0.9361(2) 0.5866(3) 0.1064(14) Uani 1 1 d . . .
N2 N 0.1816(4) 0.8074(3) 0.3554(4) 0.133(2) Uani 1 1 d . . .
O1 O 0.12666(17) 1.02421(11) 0.18154(19) 0.0725(8) Uani 1 1 d . . .
C1 C 0.0585(2) 0.97610(17) 0.0380(3) 0.0666(10) Uani 1 1 d . . .
C2 C 0.0965(2) 0.97924(17) 0.1420(3) 0.0686(10) Uani 1 1 d . . .
C3 C 0.1021(2) 0.93508(16) 0.2147(2) 0.0641(10) Uani 1 1 d . . .
C4 C 0.0751(3) 0.88828(19) 0.1780(3) 0.0772(12) Uani 1 1 d . . .
H4 H 0.0830 0.8581 0.2233 0.093 Uiso 1 1 calc R . .
C5 C 0.0352(3) 0.88400(17) 0.0731(3) 0.0702(11) Uani 1 1 d . . .
C6 C 0.0254(2) 0.93008(17) 0.0055(3) 0.0672(10) Uani 1 1 d . . .
C7 C -0.0171(3) 0.92423(19) -0.0961(3) 0.0737(11) Uani 1 1 d . . .
H7 H -0.0248 0.9538 -0.1435 0.088 Uiso 1 1 calc R . .
C8 C -0.0473(3) 0.8783(2) -0.1279(3) 0.0795(13) Uani 1 1 d . . .
H8 H -0.0778 0.8770 -0.1937 0.095 Uiso 1 1 calc R . .
C9 C -0.0338(3) 0.8322(2) -0.0642(3) 0.0883(14) Uani 1 1 d . . .
C10 C 0.0064(3) 0.8360(2) 0.0377(3) 0.0871(14) Uani 1 1 d . . .
H10 H 0.0143 0.8059 0.0832 0.105 Uiso 1 1 calc R . .
C11 C -0.0623(3) 0.7815(2) -0.1045(4) 0.0929(15) Uani 1 1 d . . .
C12 C -0.0224(6) 0.7381(4) -0.0846(6) 0.148(3) Uani 1 1 d . . .
H12 H 0.0242 0.7405 -0.0501 0.177 Uiso 1 1 calc R . .
C13 C -0.0518(6) 0.6889(4) -0.1163(7) 0.164(3) Uani 1 1 d . . .
H13 H -0.0267 0.6580 -0.0953 0.197 Uiso 1 1 calc R . .
C14 C -0.1138(5) 0.6854(3) -0.1750(6) 0.132(3) Uani 1 1 d . . .
C15 C -0.1485(7) 0.7284(4) -0.1999(9) 0.174(4) Uani 1 1 d . . .
H15 H -0.1914 0.7265 -0.2449 0.209 Uiso 1 1 calc R . .
C16 C -0.1241(5) 0.7771(3) -0.1621(6) 0.138(3) Uani 1 1 d . . .
H16 H -0.1522 0.8072 -0.1780 0.165 Uiso 1 1 calc R . .
C17 C -0.1431(9) 0.6350(4) -0.2119(10) 0.184(5) Uani 1 1 d . . .
C18 C 0.1398(3) 0.94157(18) 0.3249(3) 0.0747(12) Uani 1 1 d . . .
H18 H 0.1439 0.9765 0.3507 0.090 Uiso 1 1 calc R . .
C19 C 0.1696(3) 0.90589(19) 0.3950(3) 0.0773(12) Uani 1 1 d . . .
C20 C 0.2003(3) 0.9229(2) 0.5002(3) 0.0844(13) Uani 1 1 d . . .
C21 C 0.1749(3) 0.8506(3) 0.3707(4) 0.0967(16) Uani 1 1 d . . .
C22 C 0.1929(3) 1.04017(18) 0.1270(3) 0.0770(12) Uani 1 1 d . . .
H22A H 0.2080 1.0739 0.1602 0.092 Uiso 1 1 calc R . .
H22B H 0.1832 1.0458 0.0442 0.092 Uiso 1 1 calc R . .
C23 C 0.2544(3) 1.0030(2) 0.1382(3) 0.0810(12) Uani 1 1 d . . .
H23A H 0.2362 0.9674 0.1235 0.097 Uiso 1 1 calc R . .
H23B H 0.2726 1.0041 0.2182 0.097 Uiso 1 1 calc R . .
C24 C 0.3168(3) 1.0138(2) 0.0573(4) 0.0938(15) Uani 1 1 d . . .
H24A H 0.3180 1.0517 0.0423 0.113 Uiso 1 1 calc R . .
H24B H 0.3624 1.0048 0.0977 0.113 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
F1 C17 1.319(11) . ?
F2 C17 1.378(17) . ?
F3 C17 1.306(13) . ?
N1 C20 1.165(6) . ?
N2 C21 1.132(7) . ?
O1 C2 1.364(5) . ?
O1 C22 1.437(6) . ?
C1 C6 1.385(6) . ?
C1 C2 1.400(5) . ?
C1 C1 1.515(8) 4_575 ?
C2 C3 1.420(5) . ?
C3 C4 1.372(6) . ?
C3 C18 1.467(5) . ?
C4 C5 1.429(5) . ?
C4 H4 0.9500 . ?
C5 C10 1.405(6) . ?
C5 C6 1.434(6) . ?
C6 C7 1.425(6) . ?
C7 C8 1.358(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(6) . ?
C9 C11 1.484(7) . ?
C10 H10 0.9500 . ?
C11 C16 1.327(10) . ?
C11 C12 1.357(11) . ?
C12 C13 1.427(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.335(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.309(12) . ?
C14 C17 1.470(12) . ?
C15 C16 1.402(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.345(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.417(6) . ?
C19 C21 1.454(9) . ?
C22 C23 1.490(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.512(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.511(9) 4_575 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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 O1 C22 116.2(3) . . ?
C6 C1 C2 120.4(4) . . ?
C6 C1 C1 122.4(3) . 4_575 ?
C2 C1 C1 117.2(4) . 4_575 ?
O1 C2 C1 123.0(4) . . ?
O1 C2 C3 116.7(3) . . ?
C1 C2 C3 120.3(4) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 C18 122.9(3) . . ?
C2 C3 C18 117.6(4) . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C10 C5 C4 120.8(4) . . ?
C10 C5 C6 121.3(3) . . ?
C4 C5 C6 117.9(4) . . ?
C1 C6 C7 124.0(4) . . ?
C1 C6 C5 120.2(3) . . ?
C7 C6 C5 115.8(4) . . ?
C8 C7 C6 122.9(4) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 C11 121.1(5) . . ?
C8 C9 C11 120.5(4) . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 118.7(6) . . ?
C16 C11 C9 122.7(6) . . ?
C12 C11 C9 118.5(6) . . ?
C11 C12 C13 118.8(9) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.0(9) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.4(8) . . ?
C15 C14 C17 120.1(9) . . ?
C13 C14 C17 121.5(10) . . ?
C14 C15 C16 122.0(9) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C11 C16 C15 120.7(9) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
F3 C17 F1 108.9(12) . . ?
F3 C17 F2 103.0(10) . . ?
F1 C17 F2 99.3(9) . . ?
F3 C17 C14 115.6(10) . . ?
F1 C17 C14 114.2(9) . . ?
F2 C17 C14 114.1(13) . . ?
C19 C18 C3 130.2(4) . . ?
C19 C18 H18 114.9 . . ?
C3 C18 H18 114.9 . . ?
C18 C19 C20 118.4(4) . . ?
C18 C19 C21 125.3(4) . . ?
C20 C19 C21 116.2(4) . . ?
N1 C20 C19 178.9(6) . . ?
N2 C21 C19 176.8(6) . . ?
O1 C22 C23 115.2(4) . . ?
O1 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
O1 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 114.0(4) . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.6 . . ?
C24 C24 C23 117.5(4) 4_575 . ?
C24 C24 H24A 107.9 4_575 . ?
C23 C24 H24A 107.9 . . ?
C24 C24 H24B 107.9 4_575 . ?
C23 C24 H24B 107.9 . . ?
H24A C24 H24B 107.2 . . ?

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
C22 O1 C2 C1 -76.3(5) . . . . ?
C22 O1 C2 C3 106.7(4) . . . . ?
C6 C1 C2 O1 -176.2(4) . . . . ?
C1 C1 C2 O1 6.5(5) 4_575 . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
C1 C1 C2 C3 -176.6(3) 4_575 . . . ?
O1 C2 C3 C4 -177.7(4) . . . . ?
C1 C2 C3 C4 5.2(6) . . . . ?
O1 C2 C3 C18 -0.2(6) . . . . ?
C1 C2 C3 C18 -177.3(4) . . . . ?
C2 C3 C4 C5 -6.1(6) . . . . ?
C18 C3 C4 C5 176.5(4) . . . . ?
C3 C4 C5 C10 -178.6(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C2 C1 C6 C7 176.9(4) . . . . ?
C1 C1 C6 C7 -6.0(6) 4_575 . . . ?
C2 C1 C6 C5 -5.5(6) . . . . ?
C1 C1 C6 C5 171.6(3) 4_575 . . . ?
C10 C5 C6 C1 -175.5(5) . . . . ?
C4 C5 C6 C1 4.6(6) . . . . ?
C10 C5 C6 C7 2.3(6) . . . . ?
C4 C5 C6 C7 -177.6(4) . . . . ?
C1 C6 C7 C8 178.0(4) . . . . ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 C9 -4.1(7) . . . . ?
C7 C8 C9 C10 5.3(7) . . . . ?
C7 C8 C9 C11 -175.4(5) . . . . ?
C8 C9 C10 C5 -2.7(7) . . . . ?
C11 C9 C10 C5 178.0(5) . . . . ?
C4 C5 C10 C9 178.9(5) . . . . ?
C6 C5 C10 C9 -1.1(7) . . . . ?
C10 C9 C11 C16 147.6(6) . . . . ?
C8 C9 C11 C16 -31.7(8) . . . . ?
C10 C9 C11 C12 -34.5(8) . . . . ?
C8 C9 C11 C12 146.2(6) . . . . ?
C16 C11 C12 C13 -6.1(11) . . . . ?
C9 C11 C12 C13 175.9(7) . . . . ?
C11 C12 C13 C14 6.8(13) . . . . ?
C12 C13 C14 C15 -2.1(14) . . . . ?
C12 C13 C14 C17 177.7(10) . . . . ?
C13 C14 C15 C16 -3.0(16) . . . . ?
C17 C14 C15 C16 177.2(11) . . . . ?
C12 C11 C16 C15 1.2(12) . . . . ?
C9 C11 C16 C15 179.1(8) . . . . ?
C14 C15 C16 C11 3.7(16) . . . . ?
C15 C14 C17 F3 -176.9(12) . . . . ?
C13 C14 C17 F3 3.3(18) . . . . ?
C15 C14 C17 F1 55.6(18) . . . . ?
C13 C14 C17 F1 -124.2(12) . . . . ?
C15 C14 C17 F2 -57.7(13) . . . . ?
C13 C14 C17 F2 122.5(11) . . . . ?
C4 C3 C18 C19 16.9(8) . . . . ?
C2 C3 C18 C19 -160.5(5) . . . . ?
C3 C18 C19 C20 -177.3(5) . . . . ?
C3 C18 C19 C21 4.6(8) . . . . ?
C18 C19 C20 N1 -152(36) . . . . ?
C21 C19 C20 N1 27(37) . . . . ?
C18 C19 C21 N2 158(12) . . . . ?
C20 C19 C21 N2 -20(12) . . . . ?
C2 O1 C22 C23 -61.0(4) . . . . ?
O1 C22 C23 C24 165.8(3) . . . . ?
C22 C23 C24 C24 -92.7(6) . . . 4_575 ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.004 0.441 0.009 2298.5 404.9
_platon_squeeze_details          
;
;


_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.220
_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_14987
_database_code_depnum_ccdc_archive 'CCDC 1856064'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.67 H8.67 N1.33 O0.67'
_chemical_formula_weight         178.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.5584(3)
_cell_length_b                   18.7684(5)
_cell_length_c                   17.4034(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.951(3)
_cell_angle_gamma                90
_cell_volume                     2785.04(13)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9265
_cell_measurement_theta_min      4.6990
_cell_measurement_theta_max      71.7920

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   0.809
_exptl_transmission_factor_max   0.825
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26507
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.102
_diffrn_reflns_theta_max         71.805
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5391
_reflns_number_gt                4417
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.7156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5391
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2002(3) 0.63677(14) 0.28301(16) 0.1254(10) Uani 1 1 d . . . . .
O1 O 0.50658(13) 0.36604(6) 0.34463(7) 0.0553(3) Uani 1 1 d . . . . .
C1 C 0.32649(16) 0.36524(7) 0.44423(8) 0.0384(3) Uani 1 1 d . . . . .
C4 C 0.32211(17) 0.51453(7) 0.43439(8) 0.0436(3) Uani 1 1 d . . . . .
H4 H 0.317103 0.563820 0.429252 0.052 Uiso 1 1 calc R U . . .
N4 N 0.2143(3) -0.01574(11) 0.35104(17) 0.1148(9) Uani 1 1 d . . . . .
C8 C 0.1021(2) 0.41480(10) 0.61134(10) 0.0567(4) Uani 1 1 d . . . . .
H8 H 0.054984 0.392689 0.651236 0.068 Uiso 1 1 calc R U . . .
C7 C 0.1005(2) 0.48946(10) 0.60576(10) 0.0573(4) Uani 1 1 d . . . . .
H7 H 0.051800 0.516525 0.641576 0.069 Uiso 1 1 calc R U . . .
O2 O 0.05819(13) 0.28473(5) 0.40777(7) 0.0517(3) Uani 1 1 d . . . . .
C2 C 0.40874(17) 0.39993(7) 0.39099(8) 0.0402(3) Uani 1 1 d . . . . .
N2 N 0.6690(3) 0.63794(11) 0.21803(12) 0.0945(6) Uani 1 1 d . . . . .
C14 C 0.5782(3) 0.60719(10) 0.24889(11) 0.0656(5) Uani 1 1 d . . . . .
C13 C 0.3169(3) 0.60752(12) 0.28901(13) 0.0774(6) Uani 1 1 d . . . . .
C12 C 0.4644(2) 0.57217(9) 0.29154(10) 0.0538(4) Uani 1 1 d . . . . .
C5 C 0.24515(17) 0.48178(8) 0.49310(8) 0.0418(3) Uani 1 1 d . . . . .
C23 C 0.6044(2) 0.28570(9) 0.50542(10) 0.0551(4) Uani 1 1 d . . . . .
H23 H 0.610659 0.334542 0.497209 0.066 Uiso 1 1 calc R U . . .
C15 C 0.32587(17) 0.28555(7) 0.45128(8) 0.0403(3) Uani 1 1 d . . . . .
C18 C 0.3209(2) 0.13758(8) 0.47172(9) 0.0517(4) Uani 1 1 d . . . . .
H18 H 0.319539 0.088269 0.476885 0.062 Uiso 1 1 calc R U . . .
C9 C 0.17184(18) 0.37441(9) 0.55889(9) 0.0486(4) Uani 1 1 d . . . . .
H9 H 0.170461 0.325040 0.563285 0.058 Uiso 1 1 calc R U . . .
C10 C 0.24616(16) 0.40599(7) 0.49806(8) 0.0392(3) Uani 1 1 d . . . . .
C20 C 0.5943(2) 0.13977(9) 0.52836(11) 0.0624(5) Uani 1 1 d . . . . .
H20 H 0.592075 0.090744 0.535913 0.075 Uiso 1 1 calc R U . . .
C19 C 0.4605(2) 0.17442(8) 0.49261(9) 0.0481(4) Uani 1 1 d . . . . .
C21 C 0.7253(2) 0.17669(11) 0.55174(12) 0.0701(5) Uani 1 1 d . . . . .
H21 H 0.811617 0.153149 0.575957 0.084 Uiso 1 1 calc R U . . .
C22 C 0.7314(2) 0.25045(11) 0.53956(12) 0.0678(5) Uani 1 1 d . . . . .
H22 H 0.822531 0.275490 0.554858 0.081 Uiso 1 1 calc R U . . .
C26 C 0.0129(3) 0.06707(9) 0.40691(11) 0.0673(5) Uani 1 1 d . . . . .
C16 C 0.19000(18) 0.24761(7) 0.43302(8) 0.0419(3) Uani 1 1 d . . . . .
C27 C 0.1291(3) 0.02213(10) 0.37679(14) 0.0805(7) Uani 1 1 d . . . . .
C24 C 0.46378(18) 0.24954(7) 0.48234(8) 0.0434(3) Uani 1 1 d . . . . .
C28 C -0.1423(3) 0.03708(11) 0.40472(14) 0.0880(7) Uani 1 1 d . . . . .
C25 C 0.0383(2) 0.13380(9) 0.43338(10) 0.0578(4) Uani 1 1 d . . . . .
H25 H -0.049659 0.158614 0.446455 0.069 Uiso 1 1 calc R U . . .
C35 C -0.0442(2) 0.25806(10) 0.34324(12) 0.0663(5) Uani 1 1 d . . . . .
H35A H -0.137282 0.237077 0.362002 0.080 Uiso 1 1 calc R U . . .
H35B H 0.009555 0.221437 0.316317 0.080 Uiso 1 1 calc R U . . .
C3 C 0.40427(17) 0.47614(7) 0.38450(8) 0.0410(3) Uani 1 1 d . . . . .
N3 N -0.2647(3) 0.01312(12) 0.40351(17) 0.1210(9) Uani 1 1 d . . . . .
C34 C -0.0903(2) 0.31808(11) 0.28899(13) 0.0731(6) Uani 1 1 d . . . . .
H34A H -0.166130 0.300454 0.248838 0.088 Uiso 1 1 calc R U . . .
H34B H -0.141352 0.354735 0.317112 0.088 Uiso 1 1 calc R U . . .
C6 C 0.17017(19) 0.52207(9) 0.54799(9) 0.0510(4) Uani 1 1 d . . . . .
H6 H 0.168584 0.571511 0.544470 0.061 Uiso 1 1 calc R U . . .
C33 C 0.0431(3) 0.35080(11) 0.25212(12) 0.0750(6) Uani 1 1 d . . . . .
H33A H 0.121204 0.367974 0.291480 0.090 Uiso 1 1 calc R U . A 1
H33B H 0.006090 0.390945 0.220500 0.090 Uiso 1 1 calc R U . A 1
C11 C 0.49854(19) 0.51113(8) 0.32980(9) 0.0471(4) Uani 1 1 d . . . . .
H11 H 0.592131 0.488937 0.320355 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1866(2) 0.17179(8) 0.44399(8) 0.0471(4) Uani 1 1 d . . . . .
C29 C 0.4440(6) 0.3189(4) 0.2882(4) 0.0586(13) Uani 0.635(6) 1 d . . P B 1
H29 H 0.361896 0.290244 0.307764 0.070 Uiso 0.635(6) 1 calc R U P B 1
H6DB H 0.524912 0.287394 0.272081 0.070 Uiso 0.635(6) 1 calc R U P B 1
C30 C 0.3755(6) 0.3664(2) 0.2186(2) 0.0677(13) Uani 0.635(6) 1 d . . P B 1
H30 H 0.324815 0.407947 0.238332 0.081 Uiso 0.635(6) 1 calc R U P B 1
H8DB H 0.460547 0.382655 0.189654 0.081 Uiso 0.635(6) 1 calc R U P B 1
C31 C 0.2567(8) 0.3250(3) 0.1648(3) 0.0808(18) Uani 0.635(6) 1 d . . P B 1
H31 H 0.217805 0.356516 0.123300 0.097 Uiso 0.635(6) 1 calc R U P B 1
H5DB H 0.311381 0.286189 0.141924 0.097 Uiso 0.635(6) 1 calc R U P B 1
C32 C 0.1167(11) 0.2942(3) 0.2016(5) 0.0633(14) Uani 0.635(6) 1 d . . P B 1
H32A H 0.150008 0.253460 0.233163 0.076 Uiso 0.635(6) 1 calc R U P B 1
H32B H 0.038777 0.278076 0.161607 0.076 Uiso 0.635(6) 1 calc R U P B 1
C29' C 0.447(2) 0.3079(11) 0.2928(12) 0.136(7) Uani 0.365(6) 1 d . . P B 2
H29A H 0.505648 0.265423 0.308659 0.164 Uiso 0.365(6) 1 calc R U P B 2
H29B H 0.339148 0.299381 0.303337 0.164 Uiso 0.365(6) 1 calc R U P B 2
C30' C 0.4485(8) 0.3129(4) 0.2144(3) 0.081(2) Uani 0.365(6) 1 d . . P B 2
H30A H 0.445668 0.265634 0.191931 0.097 Uiso 0.365(6) 1 calc R U P B 2
H30B H 0.544252 0.336191 0.201806 0.097 Uiso 0.365(6) 1 calc R U P B 2
C31' C 0.3066(16) 0.3558(10) 0.1814(10) 0.158(10) Uani 0.365(6) 1 d . . P B 2
H31A H 0.311921 0.361518 0.126266 0.190 Uiso 0.365(6) 1 calc R U P B 2
H31B H 0.310089 0.402815 0.204502 0.190 Uiso 0.365(6) 1 calc R U P B 2
C32' C 0.148(2) 0.3193(8) 0.1961(10) 0.094(4) Uani 0.365(6) 1 d . . P B 2
H32A' H 0.086994 0.315783 0.146674 0.113 Uiso 0.365(6) 1 calc R U P B 2
H32B' H 0.172306 0.270998 0.212986 0.113 Uiso 0.365(6) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.137(3) . ?
O1 C2 1.3687(17) . ?
O1 C29 1.394(7) . ?
O1 C29' 1.477(18) . ?
C1 C2 1.3749(19) . ?
C1 C10 1.431(2) . ?
C1 C15 1.5007(18) . ?
C4 C3 1.369(2) . ?
C4 C5 1.404(2) . ?
N4 C27 1.138(3) . ?
C8 C9 1.363(2) . ?
C8 C7 1.405(3) . ?
C7 C6 1.358(2) . ?
O2 C16 1.3658(18) . ?
O2 C35 1.453(2) . ?
C2 C3 1.4351(19) . ?
N2 C14 1.139(2) . ?
C14 C12 1.434(2) . ?
C13 C12 1.424(3) . ?
C12 C11 1.344(2) . ?
C5 C6 1.415(2) . ?
C5 C10 1.425(2) . ?
C23 C22 1.364(2) . ?
C23 C24 1.409(2) . ?
C15 C16 1.377(2) . ?
C15 C24 1.426(2) . ?
C18 C17 1.368(2) . ?
C18 C19 1.401(2) . ?
C9 C10 1.412(2) . ?
C20 C21 1.350(3) . ?
C20 C19 1.413(2) . ?
C19 C24 1.422(2) . ?
C21 C22 1.402(3) . ?
C26 C25 1.346(2) . ?
C26 C27 1.437(3) . ?
C26 C28 1.440(3) . ?
C16 C17 1.4365(19) . ?
C28 N3 1.139(3) . ?
C25 C17 1.454(2) . ?
C35 C34 1.500(3) . ?
C3 C11 1.456(2) . ?
C34 C33 1.489(3) . ?
C33 C32' 1.503(19) . ?
C33 C32 1.547(9) . ?
C29 C30 1.575(9) . ?
C30 C31 1.532(8) . ?
C31 C32 1.521(9) . ?
C29' C30' 1.37(2) . ?
C30' C31' 1.527(13) . ?
C31' C32' 1.559(19) . ?

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 O1 C29 119.5(2) . . ?
C2 O1 C29' 120.4(7) . . ?
C2 C1 C10 119.42(12) . . ?
C2 C1 C15 122.19(13) . . ?
C10 C1 C15 118.29(12) . . ?
C3 C4 C5 122.02(13) . . ?
C9 C8 C7 120.70(16) . . ?
C6 C7 C8 119.90(15) . . ?
C16 O2 C35 119.97(13) . . ?
O1 C2 C1 123.51(13) . . ?
O1 C2 C3 115.48(12) . . ?
C1 C2 C3 120.88(13) . . ?
N2 C14 C12 176.2(2) . . ?
N1 C13 C12 176.3(2) . . ?
C11 C12 C13 124.51(16) . . ?
C11 C12 C14 121.26(17) . . ?
C13 C12 C14 114.23(15) . . ?
C4 C5 C6 121.73(14) . . ?
C4 C5 C10 118.70(13) . . ?
C6 C5 C10 119.55(14) . . ?
C22 C23 C24 121.27(16) . . ?
C16 C15 C24 119.83(13) . . ?
C16 C15 C1 120.36(13) . . ?
C24 C15 C1 119.66(12) . . ?
C17 C18 C19 122.13(14) . . ?
C8 C9 C10 121.36(15) . . ?
C9 C10 C5 117.63(13) . . ?
C9 C10 C1 122.68(13) . . ?
C5 C10 C1 119.64(13) . . ?
C21 C20 C19 121.09(16) . . ?
C18 C19 C20 121.83(14) . . ?
C18 C19 C24 118.83(14) . . ?
C20 C19 C24 119.19(15) . . ?
C20 C21 C22 120.11(17) . . ?
C23 C22 C21 120.42(18) . . ?
C25 C26 C27 125.09(19) . . ?
C25 C26 C28 119.6(2) . . ?
C27 C26 C28 115.25(17) . . ?
O2 C16 C15 117.90(12) . . ?
O2 C16 C17 121.51(13) . . ?
C15 C16 C17 120.52(14) . . ?
N4 C27 C26 176.1(2) . . ?
C23 C24 C19 117.86(14) . . ?
C23 C24 C15 122.57(13) . . ?
C19 C24 C15 119.56(14) . . ?
N3 C28 C26 179.5(3) . . ?
C26 C25 C17 127.83(19) . . ?
O2 C35 C34 109.63(15) . . ?
C4 C3 C2 119.11(13) . . ?
C4 C3 C11 121.41(13) . . ?
C2 C3 C11 119.24(13) . . ?
C33 C34 C35 114.28(17) . . ?
C7 C6 C5 120.85(15) . . ?
C34 C33 C32' 129.9(5) . . ?
C34 C33 C32 109.1(3) . . ?
C12 C11 C3 126.81(15) . . ?
C18 C17 C16 119.09(14) . . ?
C18 C17 C25 120.84(14) . . ?
C16 C17 C25 119.75(15) . . ?
O1 C29 C30 106.1(5) . . ?
C31 C30 C29 111.5(4) . . ?
C32 C31 C30 116.1(5) . . ?
C31 C32 C33 110.6(4) . . ?
C30' C29' O1 121.7(15) . . ?
C29' C30' C31' 109.6(11) . . ?
C30' C31' C32' 112.4(11) . . ?
C33 C32' C31' 120.8(11) . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.033



