# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1422762'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Cl2 N3'
_chemical_formula_weight         384.29

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.084(6)
_cell_length_b                   9.0350(12)
_cell_length_c                   17.401(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.28(3)
_cell_angle_gamma                90
_cell_volume                     1869.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2607
_cell_measurement_theta_min      4.9040
_cell_measurement_theta_max      68.7520

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    3.188
_shelx_estimated_absorpt_T_min   0.419
_shelx_estimated_absorpt_T_max   0.554
_exptl_absorpt_correction_T_min  0.50552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 16.0309
_diffrn_reflns_number            3830
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.893
_diffrn_reflns_theta_max         39.994
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1132
_reflns_number_gt                1036
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.1699P)²+6.3289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1132
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2345
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 -0.0554(7) 0.2599(8) 1.0150(4) 0.051(2) Uani 1 1 d . . . . .
H1A H -0.1236 0.2669 1.0225 0.061 Uiso 1 1 calc R U . . .
H1B H -0.0328 0.3134 0.9799 0.061 Uiso 1 1 calc R U . . .
N2 N 0.5771(6) 0.0555(8) 1.3950(5) 0.063(3) Uani 1 1 d . . . . .
H2A H 0.6338 0.1136 1.4078 0.076 Uiso 1 1 calc R U . . .
H2B H 0.5568 -0.0018 1.4295 0.076 Uiso 1 1 calc R U . . .
N3 N 0.3427(7) -0.5815(12) 1.0443(5) 0.084(3) Uani 1 1 d . . . . .
H3A H 0.3663 -0.6191 1.0048 0.101 Uiso 1 1 calc R U . . .
H3B H 0.3218 -0.6385 1.0786 0.101 Uiso 1 1 calc R U . . .
C1 C 0.0189(10) 0.1616(11) 1.0598(6) 0.036(3) Uani 1 1 d . . . . .
C2 C -0.0123(8) 0.0735(13) 1.1167(7) 0.041(3) Uani 1 1 d . . . . .
H2 H -0.0862 0.0773 1.1251 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0631(11) -0.0208(10) 1.1618(5) 0.043(3) Uani 1 1 d . . . . .
H3 H 0.0396 -0.0784 1.2002 0.051 Uiso 1 1 calc R U . . .
C4 C 0.1724(9) -0.0300(10) 1.1503(5) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.2052(8) 0.0592(11) 1.0930(6) 0.036(3) Uani 1 1 d . . . . .
C6 C 0.1298(10) 0.1536(10) 1.0477(5) 0.036(3) Uani 1 1 d . . . . .
H6 H 0.1531 0.2115 1.0094 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5179(9) 0.0542(12) 1.3183(6) 0.039(3) Uani 1 1 d . . . . .
C8 C 0.4244(10) -0.0385(10) 1.2984(7) 0.044(3) Uani 1 1 d . . . . .
H8 H 0.4026 -0.1010 1.3355 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3652(7) -0.0359(10) 1.2231(7) 0.036(3) Uani 1 1 d . . . . .
C10 C 0.3975(9) 0.0540(11) 1.1663(6) 0.037(3) Uani 1 1 d . . . . .
C11 C 0.4891(10) 0.1439(10) 1.1876(7) 0.044(3) Uani 1 1 d . . . . .
H11 H 0.5113 0.2060 1.1505 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5488(8) 0.1446(11) 1.2624(9) 0.051(3) Uani 1 1 d . . . . .
H12 H 0.6106 0.2068 1.2753 0.061 Uiso 1 1 calc R U . . .
C13 C 0.3386(8) -0.4328(14) 1.0525(9) 0.054(3) Uani 1 1 d . . . . .
C14 C 0.3723(8) -0.3420(19) 0.9973(6) 0.053(3) Uani 1 1 d . . . . .
H14 H 0.3976 -0.3831 0.9546 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3685(7) -0.1919(15) 1.0050(7) 0.046(3) Uani 1 1 d . . . . .
H15 H 0.3905 -0.1316 0.9671 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3326(7) -0.1285(12) 1.0682(7) 0.037(3) Uani 1 1 d . . . . .
C17 C 0.3001(7) -0.2207(15) 1.1244(6) 0.037(3) Uani 1 1 d . . . . .
C18 C 0.3026(7) -0.3711(16) 1.1180(6) 0.046(3) Uani 1 1 d . . . . .
H18 H 0.2810 -0.4313 1.1560 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3260(8) 0.0334(10) 1.0856(5) 0.035(2) Uani 1 1 d . . . . .
H19 H 0.3504 0.0962 1.0458 0.042 Uiso 1 1 calc R U . . .
C20 C 0.2637(7) -0.1328(10) 1.1898(5) 0.036(3) Uani 1 1 d . . . . .
H20 H 0.2391 -0.1958 1.2294 0.043 Uiso 1 1 calc R U . . .
C111 C 0.3989(9) 0.2466(12) 0.8132(7) 0.090(4) Uani 1 1 d . . . . .
H11A H 0.4780 0.2406 0.8365 0.107 Uiso 1 1 calc R U . . .
H11B H 0.3886 0.1978 0.7628 0.107 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3184(2) 0.1559(3) 0.87372(15) 0.0800(13) Uani 1 1 d . . . . .
Cl2 Cl 0.3591(3) 0.4328(4) 0.8005(2) 0.1085(15) 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 C1 1.398(11) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C7 1.397(11) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C13 1.353(12) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C1 C2 1.374(12) . ?
C1 C6 1.394(12) . ?
C2 C3 1.385(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(11) . ?
C4 C20 1.511(12) . ?
C5 C6 1.386(11) . ?
C5 C19 1.506(12) . ?
C6 H6 0.9300 . ?
C7 C12 1.373(12) . ?
C7 C8 1.399(12) . ?
C8 C9 1.377(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(11) . ?
C9 C20 1.533(12) . ?
C10 C11 1.370(12) . ?
C10 C19 1.522(12) . ?
C11 C12 1.370(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.379(13) . ?
C13 C18 1.406(14) . ?
C14 C15 1.364(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(12) . ?
C16 C19 1.499(13) . ?
C17 C18 1.364(13) . ?
C17 C20 1.516(12) . ?
C18 H18 0.9300 . ?
C19 H19 0.9800 . ?
C20 H20 0.9800 . ?
C111 Cl2 1.753(12) . ?
C111 Cl1 1.759(12) . ?
C111 H11A 0.9700 . ?
C111 H11B 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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 H2A 120.0 . . ?
C7 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 H3A 120.0 . . ?
C13 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 C1 C6 118.3(8) . . ?
C2 C1 N1 122.6(10) . . ?
C6 C1 N1 119.2(11) . . ?
C1 C2 C3 121.8(8) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 120.5(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.2(8) . . ?
C3 C4 C20 127.9(10) . . ?
C5 C4 C20 113.8(9) . . ?
C6 C5 C4 121.3(8) . . ?
C6 C5 C19 126.6(10) . . ?
C4 C5 C19 112.0(10) . . ?
C5 C6 C1 119.9(8) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 N2 121.0(11) . . ?
C12 C7 C8 119.4(8) . . ?
N2 C7 C8 119.7(11) . . ?
C9 C8 C7 119.0(8) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.6(8) . . ?
C8 C9 C20 126.4(10) . . ?
C10 C9 C20 111.9(9) . . ?
C11 C10 C9 118.1(8) . . ?
C11 C10 C19 128.3(11) . . ?
C9 C10 C19 113.6(9) . . ?
C10 C11 C12 121.5(8) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 120.5(9) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N3 C13 C14 119.8(14) . . ?
N3 C13 C18 120.1(14) . . ?
C14 C13 C18 120.0(9) . . ?
C15 C14 C13 120.2(9) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.9(9) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.7(9) . . ?
C15 C16 C19 127.1(11) . . ?
C17 C16 C19 114.2(10) . . ?
C18 C17 C16 121.6(9) . . ?
C18 C17 C20 126.7(11) . . ?
C16 C17 C20 111.7(10) . . ?
C17 C18 C13 118.5(10) . . ?
C17 C18 H18 120.8 . . ?
C13 C18 H18 120.8 . . ?
C16 C19 C5 104.8(7) . . ?
C16 C19 C10 105.3(7) . . ?
C5 C19 C10 107.6(7) . . ?
C16 C19 H19 112.8 . . ?
C5 C19 H19 112.8 . . ?
C10 C19 H19 112.8 . . ?
C4 C20 C17 105.5(7) . . ?
C4 C20 C9 106.9(7) . . ?
C17 C20 C9 105.2(7) . . ?
C4 C20 H20 112.9 . . ?
C17 C20 H20 112.9 . . ?
C9 C20 H20 112.9 . . ?
Cl2 C111 Cl1 110.7(6) . . ?
Cl2 C111 H11A 109.5 . . ?
Cl1 C111 H11A 109.5 . . ?
Cl2 C111 H11B 109.5 . . ?
Cl1 C111 H11B 109.5 . . ?
H11A C111 H11B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(11) . . . . ?
N1 C1 C2 C3 -178.5(7) . . . . ?
C1 C2 C3 C4 -0.6(12) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C2 C3 C4 C20 -175.7(8) . . . . ?
C3 C4 C5 C6 -0.8(11) . . . . ?
C20 C4 C5 C6 176.1(7) . . . . ?
C3 C4 C5 C19 -178.3(7) . . . . ?
C20 C4 C5 C19 -1.3(10) . . . . ?
C4 C5 C6 C1 0.7(11) . . . . ?
C19 C5 C6 C1 177.7(7) . . . . ?
C2 C1 C6 C5 -0.5(11) . . . . ?
N1 C1 C6 C5 178.5(7) . . . . ?
C12 C7 C8 C9 -0.4(11) . . . . ?
N2 C7 C8 C9 178.4(7) . . . . ?
C7 C8 C9 C10 1.4(12) . . . . ?
C7 C8 C9 C20 177.7(7) . . . . ?
C8 C9 C10 C11 -1.7(11) . . . . ?
C20 C9 C10 C11 -178.4(7) . . . . ?
C8 C9 C10 C19 176.1(7) . . . . ?
C20 C9 C10 C19 -0.6(10) . . . . ?
C9 C10 C11 C12 0.9(11) . . . . ?
C19 C10 C11 C12 -176.5(8) . . . . ?
C10 C11 C12 C7 0.0(12) . . . . ?
N2 C7 C12 C11 -179.1(7) . . . . ?
C8 C7 C12 C11 -0.3(12) . . . . ?
N3 C13 C14 C15 -179.9(8) . . . . ?
C18 C13 C14 C15 -1.4(13) . . . . ?
C13 C14 C15 C16 0.8(13) . . . . ?
C14 C15 C16 C17 0.1(12) . . . . ?
C14 C15 C16 C19 178.7(8) . . . . ?
C15 C16 C17 C18 -0.3(12) . . . . ?
C19 C16 C17 C18 -179.1(7) . . . . ?
C15 C16 C17 C20 179.7(7) . . . . ?
C19 C16 C17 C20 0.9(10) . . . . ?
C16 C17 C18 C13 -0.3(12) . . . . ?
C20 C17 C18 C13 179.7(7) . . . . ?
N3 C13 C18 C17 179.7(8) . . . . ?
C14 C13 C18 C17 1.2(12) . . . . ?
C15 C16 C19 C5 123.6(9) . . . . ?
C17 C16 C19 C5 -57.8(9) . . . . ?
C15 C16 C19 C10 -123.1(9) . . . . ?
C17 C16 C19 C10 55.6(9) . . . . ?
C6 C5 C19 C16 -119.9(9) . . . . ?
C4 C5 C19 C16 57.4(9) . . . . ?
C6 C5 C19 C10 128.4(8) . . . . ?
C4 C5 C19 C10 -54.3(9) . . . . ?
C11 C10 C19 C16 122.0(9) . . . . ?
C9 C10 C19 C16 -55.5(10) . . . . ?
C11 C10 C19 C5 -126.6(9) . . . . ?
C9 C10 C19 C5 55.8(9) . . . . ?
C3 C4 C20 C17 121.1(9) . . . . ?
C5 C4 C20 C17 -55.5(9) . . . . ?
C3 C4 C20 C9 -127.3(9) . . . . ?
C5 C4 C20 C9 56.1(9) . . . . ?
C18 C17 C20 C4 -124.7(9) . . . . ?
C16 C17 C20 C4 55.2(9) . . . . ?
C18 C17 C20 C9 122.4(9) . . . . ?
C16 C17 C20 C9 -57.6(9) . . . . ?
C8 C9 C20 C4 129.0(8) . . . . ?
C10 C9 C20 C4 -54.4(9) . . . . ?
C8 C9 C20 C17 -119.2(9) . . . . ?
C10 C9 C20 C17 57.4(9) . . . . ?

_refine_diff_density_max         1.065
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.082

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1422763'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H26 N2 O'
_chemical_formula_weight         550.63

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.6315(7)
_cell_length_b                   11.8390(9)
_cell_length_c                   12.1481(8)
_cell_angle_alpha                87.279(6)
_cell_angle_beta                 68.228(6)
_cell_angle_gamma                86.725(6)
_cell_volume                     1417.08(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3234
_cell_measurement_theta_min      3.9250
_cell_measurement_theta_max      70.4760

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_T_min  0.90865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            9377
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.741
_diffrn_reflns_theta_max         71.277
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5357
_reflns_number_gt                4002
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0686P)²+0.2994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5357
_refine_ls_number_parameters     464
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.024
_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
C4B C 0.2558(8) 0.7673(8) 0.6394(8) 0.0424(10) Uani 0.622(10) 1 d DG . P A 2
C20B C 0.3296(7) 0.6668(8) 0.5995(7) 0.0417(12) Uani 0.622(10) 1 d DG . P A 2
C57A C 0.2956(7) 0.5994(6) 0.5249(5) 0.0498(13) Uani 0.622(10) 1 d G . P A 2
H57A H 0.3450 0.5321 0.4982 0.060 Uiso 0.622(10) 1 calc R U P A 2
C56B C 0.1879(7) 0.6324(5) 0.4903(5) 0.0453(14) Uani 0.622(10) 1 d DG U P A 2
C42B C 0.1141(6) 0.7329(5) 0.5302(6) 0.0429(14) Uani 0.622(10) 1 d DG U P A 2
H42B H 0.0421 0.7550 0.5070 0.052 Uiso 0.622(10) 1 calc R U P A 2
C10B C 0.1481(7) 0.8004(6) 0.6047(8) 0.0439(12) Uani 0.622(10) 1 d DG U P A 2
H10B H 0.0988 0.8676 0.6314 0.053 Uiso 0.622(10) 1 calc R U P A 2
C1 C 0.10783(19) 0.22865(17) 0.03538(17) 0.0499(5) Uani 1 1 d . . . . .
H1B H 0.0344 0.2339 0.0047 0.060 Uiso 0.622(10) 1 calc R U P A 2
H1A H 0.0325 0.2375 0.0072 0.060 Uiso 0.378(10) 1 calc R U P A 1
C7 C 0.2473(2) 0.23480(17) -0.06290(17) 0.0500(5) Uani 1 1 d . . . . .
C13 C 0.1102(2) 0.11777(17) 0.10361(16) 0.0498(5) Uani 1 1 d . . . . .
C14 C 0.31640(19) 0.83229(16) 0.71506(16) 0.0464(4) Uani 1 1 d . U . . .
H14A H 0.2675 0.9042 0.7438 0.056 Uiso 0.622(10) 1 calc R U P A 2
H14 H 0.2712 0.9048 0.7463 0.056 Uiso 0.378(10) 1 calc R U P A 1
C8 C 0.31267(19) 0.74712(16) 0.81424(17) 0.0479(4) Uani 1 1 d . U . . .
C9 C 0.4658(2) 0.84510(16) 0.64071(17) 0.0484(4) Uani 1 1 d . U . . .
C11 C 0.5344(2) 0.74249(18) 0.59852(17) 0.0525(5) Uani 1 1 d . U . . .
C3 C 0.0205(2) 0.03135(19) 0.12772(18) 0.0573(5) Uani 1 1 d . . . . .
H3 H -0.0501 0.0369 0.0998 0.069 Uiso 1 1 calc R U . . .
C12B C 0.0928(6) 0.3177(4) 0.1235(6) 0.0473(10) Uani 0.622(10) 1 d DG U P A 2
C18 C 0.1930(6) 0.3137(4) 0.1716(6) 0.0487(15) Uani 0.622(10) 1 d DG U P A 2
C34 C 0.1950(6) 0.3973(5) 0.2474(5) 0.0519(12) Uani 0.622(10) 1 d DG U P A 2
H34 H 0.2621 0.3946 0.2795 0.062 Uiso 0.622(10) 1 calc R U P A 2
C50 C 0.0967(6) 0.4850(4) 0.2751(4) 0.0461(12) Uani 0.622(10) 1 d DG U P A 2
C38 C -0.0036(5) 0.4891(3) 0.2271(4) 0.0532(13) Uani 0.622(10) 1 d DG U P A 2
H38 H -0.0693 0.5478 0.2457 0.064 Uiso 0.622(10) 1 calc R U P A 2
C23 C -0.0055(5) 0.4055(4) 0.1513(5) 0.0489(11) Uani 0.622(10) 1 d DG U P A 2
H23 H -0.0726 0.4082 0.1191 0.059 Uiso 0.622(10) 1 calc R U P A 2
C24 C 0.3791(2) 0.64467(17) 0.77234(19) 0.0547(5) Uani 1 1 d . U . . .
C15 C 0.2757(2) 0.24825(19) -0.18309(18) 0.0595(5) Uani 1 1 d . . . . .
H15 H 0.2058 0.2558 -0.2118 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2969(14) 0.2158(10) 0.1232(10) 0.0503(13) Uani 0.622(10) 1 d D U P A 2
H5 H 0.3689 0.2110 0.1556 0.060 Uiso 0.622(10) 1 calc R U P A 2
C16B C 0.429(4) 0.650(3) 0.633(4) 0.052(2) Uani 0.378(10) 1 d . . P A 1
H16B H 0.4731 0.5775 0.6006 0.063 Uiso 0.378(10) 1 calc R U P A 1
C17 C 0.2155(2) 0.10757(18) 0.14618(18) 0.0561(5) Uani 1 1 d . . . . .
C19 C 0.2519(2) 0.7637(2) 0.93516(18) 0.0584(5) Uani 1 1 d . . . . .
H19 H 0.2098 0.8332 0.9632 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3529(2) 0.22391(18) -0.02042(19) 0.0549(5) Uani 1 1 d . . . . .
C21 C 0.5345(2) 0.9439(2) 0.6143(2) 0.0629(6) Uani 1 1 d . . . . .
H21 H 0.4901 1.0126 0.6426 0.075 Uiso 1 1 calc R U . . .
C25 C 0.6707(2) 0.7391(2) 0.5304(2) 0.0677(6) Uani 1 1 d . . . . .
H25 H 0.7160 0.6705 0.5031 0.081 Uiso 1 1 calc R U . . .
C26 C 0.0363(3) -0.06365(19) 0.1938(2) 0.0685(7) Uani 1 1 d . . . . .
H26 H -0.0242 -0.1215 0.2103 0.082 Uiso 1 1 calc R U . . .
C27 C 0.4856(2) 0.2251(2) -0.0984(2) 0.0703(6) Uani 1 1 d . . . . .
H27 H 0.5560 0.2172 -0.0703 0.084 Uiso 1 1 calc R U . . .
C35 C 0.2315(3) 0.0131(2) 0.2106(2) 0.0713(7) Uani 1 1 d . . . . .
H35 H 0.3028 0.0069 0.2378 0.086 Uiso 1 1 calc R U . . .
C30 C 0.6730(3) 0.9387(3) 0.5439(2) 0.0782(8) Uani 1 1 d . . . . .
H30 H 0.7205 1.0049 0.5246 0.094 Uiso 1 1 calc R U . . .
C28 C 0.7393(3) 0.8378(3) 0.5029(2) 0.0768(7) Uani 1 1 d . . . . .
H28 H 0.8313 0.8360 0.4563 0.092 Uiso 1 1 calc R U . . .
C29 C 0.4102(3) 0.2504(2) -0.2607(2) 0.0713(7) Uani 1 1 d . . . . .
H29 H 0.4301 0.2602 -0.3418 0.086 Uiso 1 1 calc R U . . .
C31 C 0.3832(3) 0.5576(2) 0.8517(3) 0.0750(7) Uani 1 1 d . . . . .
H31 H 0.4279 0.4886 0.8248 0.090 Uiso 1 1 calc R U . . .
C33 C 0.1408(3) -0.0729(2) 0.2351(2) 0.0754(7) Uani 1 1 d . . . . .
H33 H 0.1507 -0.1367 0.2793 0.091 Uiso 1 1 calc R U . . .
C37 C 0.2546(3) 0.6763(2) 1.0134(2) 0.0736(7) Uani 1 1 d . . . . .
H37 H 0.2120 0.6862 1.0945 0.088 Uiso 1 1 calc R U . . .
C36 C 0.5134(3) 0.2382(2) -0.2192(2) 0.0751(7) Uani 1 1 d . . . . .
H36 H 0.6029 0.2387 -0.2722 0.090 Uiso 1 1 calc R U . . .
C41 C 0.3191(3) 0.5757(3) 0.9728(3) 0.0830(8) Uani 1 1 d . . . . .
H41 H 0.3205 0.5178 1.0268 0.100 Uiso 1 1 calc R U . . .
C39 C 0.314(3) 0.2019(17) 0.0991(19) 0.0503(13) Uani 0.378(10) 1 d D . P A 1
H39 H 0.3918 0.1925 0.1247 0.060 Uiso 0.378(10) 1 calc R U P A 1
C12A C 0.1147(10) 0.3279(8) 0.1143(10) 0.0473(10) Uani 0.378(10) 1 d G . P A 1
C52 C 0.0209(9) 0.4158(6) 0.1634(9) 0.062(2) Uani 0.378(10) 1 d DG . P A 1
H52 H -0.0519 0.4302 0.1392 0.074 Uiso 0.378(10) 1 calc R U P A 1
C60 C 0.0359(8) 0.4821(5) 0.2488(7) 0.046(2) Uani 0.378(10) 1 d DG . P A 1
H60 H -0.0269 0.5409 0.2816 0.055 Uiso 0.378(10) 1 calc R U P A 1
C48 C 0.1447(9) 0.4606(6) 0.2851(5) 0.0436(17) Uani 0.378(10) 1 d DG . P A 1
C58 C 0.2386(9) 0.3727(7) 0.2360(8) 0.0442(18) Uani 0.378(10) 1 d G . P A 1
H58 H 0.3114 0.3583 0.2603 0.053 Uiso 0.378(10) 1 calc R U P A 1
C59 C 0.2236(10) 0.3064(8) 0.1506(10) 0.046(2) Uani 0.378(10) 1 d DG . P A 1
C20A C 0.3213(12) 0.6834(14) 0.5850(12) 0.057(4) Uani 0.378(10) 1 d G . P A 1
C57B C 0.2723(13) 0.6273(9) 0.5122(9) 0.055(3) Uani 0.378(10) 1 d G . P A 1
H57B H 0.3151 0.5600 0.4778 0.066 Uiso 0.378(10) 1 calc R U P A 1
C56A C 0.1593(12) 0.6717(8) 0.4908(8) 0.045(2) Uani 0.378(10) 1 d G . P A 1
C42A C 0.0954(10) 0.7723(8) 0.5423(11) 0.045(2) Uani 0.378(10) 1 d G . P A 1
H42A H 0.0198 0.8020 0.5280 0.054 Uiso 0.378(10) 1 calc R U P A 1
C10A C 0.1444(13) 0.8284(10) 0.6150(14) 0.052(2) Uani 0.378(10) 1 d G . P A 1
H10A H 0.1017 0.8957 0.6494 0.062 Uiso 0.378(10) 1 calc R U P A 1
C4A C 0.2574(14) 0.7840(14) 0.6364(15) 0.0424(10) Uani 0.378(10) 1 d G . P A 1
C16A C 0.449(2) 0.6388(19) 0.641(2) 0.052(2) Uani 0.622(10) 1 d . . P A 2
H16A H 0.4980 0.5667 0.6131 0.063 Uiso 0.622(10) 1 calc R U P A 2
O1B O 0.0235(15) 0.6682(9) 0.3622(11) 0.0773(18) Uani 0.622(10) 1 d . . P A 2
N2B N 0.1804(7) 0.5223(6) 0.3630(7) 0.0536(19) Uani 0.378(10) 1 d . . P A 1
N3B N 0.0960(3) 0.5717(3) 0.3573(4) 0.0531(14) Uani 0.622(10) 1 d . . P A 2
N2A N 0.1764(4) 0.5509(4) 0.4117(5) 0.0547(11) Uani 0.622(10) 1 d . . P A 2
N3A N 0.1150(5) 0.6158(6) 0.4090(5) 0.0467(19) Uani 0.378(10) 1 d . . P A 1
O1A O 0.009(3) 0.6441(15) 0.3902(19) 0.0773(18) Uani 0.378(10) 1 d . . P A 1


_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
C4B C20B 1.3900 . ?
C4B C10B 1.3900 . ?
C4B C14 1.554(5) . ?
C20B C57A 1.3900 . ?
C20B C16A 1.543(17) . ?
C57A C56B 1.3900 . ?
C57A H57A 0.9300 . ?
C56B C42B 1.3900 . ?
C56B N2A 1.431(8) . ?
C42B C10B 1.3900 . ?
C42B H42B 0.9300 . ?
C10B H10B 0.9300 . ?
C1 C12B 1.498(4) . ?
C1 C13 1.523(3) . ?
C1 C7 1.524(3) . ?
C1 C12A 1.573(5) . ?
C1 H1B 0.9800 . ?
C1 H1A 0.9800 . ?
C7 C15 1.380(3) . ?
C7 C6 1.396(3) . ?
C13 C3 1.385(3) . ?
C13 C17 1.393(3) . ?
C14 C4A 1.474(9) . ?
C14 C9 1.521(3) . ?
C14 C8 1.524(3) . ?
C14 H14A 0.9800 . ?
C14 H14 0.9800 . ?
C8 C24 1.387(3) . ?
C8 C19 1.386(3) . ?
C9 C21 1.376(3) . ?
C9 C11 1.397(3) . ?
C11 C25 1.376(3) . ?
C11 C16B 1.54(5) . ?
C11 C16A 1.52(3) . ?
C3 C26 1.390(3) . ?
C3 H3 0.9300 . ?
C12B C18 1.3900 . ?
C12B C23 1.3900 . ?
C18 C34 1.3900 . ?
C18 C5 1.531(5) . ?
C34 C50 1.3900 . ?
C34 H34 0.9300 . ?
C50 C38 1.3900 . ?
C50 N3B 1.463(6) . ?
C38 C23 1.3900 . ?
C38 H38 0.9300 . ?
C23 H23 0.9300 . ?
C24 C31 1.388(3) . ?
C24 C16A 1.50(3) . ?
C24 C16B 1.58(5) . ?
C15 C29 1.392(3) . ?
C15 H15 0.9300 . ?
C5 C17 1.544(17) . ?
C5 C6 1.621(12) . ?
C5 H5 0.9800 . ?
C16B C20A 1.49(3) . ?
C16B H16B 0.9800 . ?
C17 C35 1.373(3) . ?
C17 C39 1.52(3) . ?
C19 C37 1.378(3) . ?
C19 H19 0.9300 . ?
C6 C27 1.377(3) . ?
C6 C39 1.37(2) . ?
C21 C30 1.401(4) . ?
C21 H21 0.9300 . ?
C25 C28 1.374(4) . ?
C25 H25 0.9300 . ?
C26 C33 1.375(4) . ?
C26 H26 0.9300 . ?
C27 C36 1.388(4) . ?
C27 H27 0.9300 . ?
C35 C33 1.388(3) . ?
C35 H35 0.9300 . ?
C30 C28 1.368(4) . ?
C30 H30 0.9300 . ?
C28 H28 0.9300 . ?
C29 C36 1.365(4) . ?
C29 H29 0.9300 . ?
C31 C41 1.394(4) . ?
C31 H31 0.9300 . ?
C33 H33 0.9300 . ?
C37 C41 1.357(4) . ?
C37 H37 0.9300 . ?
C36 H36 0.9300 . ?
C41 H41 0.9300 . ?
C39 C59 1.531(7) . ?
C39 H39 0.9800 . ?
C12A C52 1.3900 . ?
C12A C59 1.3900 . ?
C52 C60 1.3900 . ?
C52 H52 0.9300 . ?
C60 C48 1.3900 . ?
C60 H60 0.9300 . ?
C48 N2B 1.392(11) . ?
C48 C58 1.3900 . ?
C58 C59 1.3900 . ?
C58 H58 0.9300 . ?
C20A C57B 1.3900 . ?
C20A C4A 1.3900 . ?
C57B C56A 1.3900 . ?
C57B H57B 0.9300 . ?
C56A C42A 1.3900 . ?
C56A N3A 1.447(11) . ?
C42A C10A 1.3900 . ?
C42A H42A 0.9300 . ?
C10A C4A 1.3900 . ?
C10A H10A 0.9300 . ?
C16A H16A 0.9800 . ?
O1B N3B 1.332(12) . ?
N2B N3A 1.305(13) . ?
N3B N2A 1.268(8) . ?
N3A O1A 1.25(2) . ?

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
C20B C4B C10B 120.0 . . ?
C20B C4B C14 111.3(4) . . ?
C10B C4B C14 128.6(5) . . ?
C57A C20B C4B 120.0 . . ?
C57A C20B C16A 123.9(10) . . ?
C4B C20B C16A 116.1(10) . . ?
C20B C57A C56B 120.0 . . ?
C20B C57A H57A 120.0 . . ?
C56B C57A H57A 120.0 . . ?
C42B C56B C57A 120.0 . . ?
C42B C56B N2A 130.9(4) . . ?
C57A C56B N2A 109.1(4) . . ?
C10B C42B C56B 120.0 . . ?
C10B C42B H42B 120.0 . . ?
C56B C42B H42B 120.0 . . ?
C42B C10B C4B 120.0 . . ?
C42B C10B H10B 120.0 . . ?
C4B C10B H10B 120.0 . . ?
C12B C1 C13 104.0(3) . . ?
C12B C1 C7 109.1(3) . . ?
C13 C1 C7 105.91(16) . . ?
C13 C1 C12A 107.8(5) . . ?
C7 C1 C12A 100.1(5) . . ?
C12B C1 H1B 112.4 . . ?
C13 C1 H1B 112.4 . . ?
C7 C1 H1B 112.4 . . ?
C13 C1 H1A 114.0 . . ?
C7 C1 H1A 114.0 . . ?
C12A C1 H1A 114.0 . . ?
C15 C7 C6 120.06(19) . . ?
C15 C7 C1 127.00(19) . . ?
C6 C7 C1 112.93(17) . . ?
C3 C13 C17 119.1(2) . . ?
C3 C13 C1 127.44(19) . . ?
C17 C13 C1 113.43(17) . . ?
C4A C14 C9 105.9(7) . . ?
C4A C14 C8 109.9(8) . . ?
C9 C14 C8 105.54(15) . . ?
C9 C14 C4B 106.8(4) . . ?
C8 C14 C4B 103.2(4) . . ?
C9 C14 H14A 113.5 . . ?
C8 C14 H14A 113.5 . . ?
C4B C14 H14A 113.5 . . ?
C4A C14 H14 111.7 . . ?
C9 C14 H14 111.7 . . ?
C8 C14 H14 111.7 . . ?
C24 C8 C19 120.3(2) . . ?
C24 C8 C14 112.88(17) . . ?
C19 C8 C14 126.78(19) . . ?
C21 C9 C11 120.0(2) . . ?
C21 C9 C14 126.8(2) . . ?
C11 C9 C14 113.14(16) . . ?
C25 C11 C9 120.5(2) . . ?
C25 C11 C16B 131.4(13) . . ?
C9 C11 C16B 107.9(12) . . ?
C25 C11 C16A 124.6(7) . . ?
C9 C11 C16A 114.7(7) . . ?
C13 C3 C26 119.8(2) . . ?
C13 C3 H3 120.1 . . ?
C26 C3 H3 120.1 . . ?
C18 C12B C23 120.0 . . ?
C18 C12B C1 115.1(3) . . ?
C23 C12B C1 124.7(3) . . ?
C12B C18 C34 120.0 . . ?
C12B C18 C5 111.8(6) . . ?
C34 C18 C5 128.0(6) . . ?
C18 C34 C50 120.0 . . ?
C18 C34 H34 120.0 . . ?
C50 C34 H34 120.0 . . ?
C38 C50 C34 120.0 . . ?
C38 C50 N3B 119.7(4) . . ?
C34 C50 N3B 120.3(4) . . ?
C50 C38 C23 120.0 . . ?
C50 C38 H38 120.0 . . ?
C23 C38 H38 120.0 . . ?
C38 C23 C12B 120.0 . . ?
C38 C23 H23 120.0 . . ?
C12B C23 H23 120.0 . . ?
C8 C24 C31 119.9(2) . . ?
C8 C24 C16A 115.8(7) . . ?
C31 C24 C16A 124.2(7) . . ?
C8 C24 C16B 108.1(12) . . ?
C31 C24 C16B 131.9(12) . . ?
C7 C15 C29 119.2(2) . . ?
C7 C15 H15 120.4 . . ?
C29 C15 H15 120.4 . . ?
C18 C5 C17 106.3(9) . . ?
C18 C5 C6 108.5(7) . . ?
C17 C5 C6 100.2(7) . . ?
C18 C5 H5 113.6 . . ?
C17 C5 H5 113.6 . . ?
C6 C5 H5 113.6 . . ?
C20A C16B C11 109(2) . . ?
C20A C16B C24 115(2) . . ?
C11 C16B C24 103(3) . . ?
C20A C16B H16B 110.0 . . ?
C11 C16B H16B 110.0 . . ?
C24 C16B H16B 110.0 . . ?
C35 C17 C13 120.9(2) . . ?
C35 C17 C39 126.2(8) . . ?
C13 C17 C39 112.4(8) . . ?
C35 C17 C5 126.2(5) . . ?
C13 C17 C5 112.6(5) . . ?
C37 C19 C8 119.4(2) . . ?
C37 C19 H19 120.3 . . ?
C8 C19 H19 120.3 . . ?
C27 C6 C39 124.2(10) . . ?
C27 C6 C7 120.1(2) . . ?
C39 C6 C7 115.4(11) . . ?
C27 C6 C5 128.0(5) . . ?
C7 C6 C5 111.8(5) . . ?
C9 C21 C30 118.5(2) . . ?
C9 C21 H21 120.7 . . ?
C30 C21 H21 120.7 . . ?
C28 C25 C11 119.6(3) . . ?
C28 C25 H25 120.2 . . ?
C11 C25 H25 120.2 . . ?
C33 C26 C3 120.6(2) . . ?
C33 C26 H26 119.7 . . ?
C3 C26 H26 119.7 . . ?
C6 C27 C36 119.6(2) . . ?
C6 C27 H27 120.2 . . ?
C36 C27 H27 120.2 . . ?
C17 C35 C33 119.7(2) . . ?
C17 C35 H35 120.2 . . ?
C33 C35 H35 120.2 . . ?
C28 C30 C21 121.1(2) . . ?
C28 C30 H30 119.5 . . ?
C21 C30 H30 119.5 . . ?
C30 C28 C25 120.3(2) . . ?
C30 C28 H28 119.9 . . ?
C25 C28 H28 119.9 . . ?
C36 C29 C15 120.7(2) . . ?
C36 C29 H29 119.6 . . ?
C15 C29 H29 119.6 . . ?
C24 C31 C41 118.6(2) . . ?
C24 C31 H31 120.7 . . ?
C41 C31 H31 120.7 . . ?
C26 C33 C35 119.9(2) . . ?
C26 C33 H33 120.0 . . ?
C35 C33 H33 120.0 . . ?
C41 C37 C19 120.5(2) . . ?
C41 C37 H37 119.8 . . ?
C19 C37 H37 119.8 . . ?
C29 C36 C27 120.4(2) . . ?
C29 C36 H36 119.8 . . ?
C27 C36 H36 119.8 . . ?
C37 C41 C31 121.3(2) . . ?
C37 C41 H41 119.3 . . ?
C31 C41 H41 119.3 . . ?
C6 C39 C17 114.2(17) . . ?
C6 C39 C59 101.8(12) . . ?
C17 C39 C59 101.6(14) . . ?
C6 C39 H39 112.7 . . ?
C17 C39 H39 112.7 . . ?
C59 C39 H39 112.7 . . ?
C52 C12A C59 120.0 . . ?
C52 C12A C1 129.8(4) . . ?
C59 C12A C1 109.3(4) . . ?
C12A C52 C60 120.0 . . ?
C12A C52 H52 120.0 . . ?
C60 C52 H52 120.0 . . ?
C48 C60 C52 120.0 . . ?
C48 C60 H60 120.0 . . ?
C52 C60 H60 120.0 . . ?
N2B C48 C60 127.8(6) . . ?
N2B C48 C58 112.1(6) . . ?
C60 C48 C58 120.0 . . ?
C59 C58 C48 120.0 . . ?
C59 C58 H58 120.0 . . ?
C48 C58 H58 120.0 . . ?
C58 C59 C12A 120.0 . . ?
C58 C59 C39 123.8(10) . . ?
C12A C59 C39 116.0(11) . . ?
C57B C20A C4A 120.0 . . ?
C57B C20A C16B 131.3(19) . . ?
C4A C20A C16B 108.3(19) . . ?
C20A C57B C56A 120.0 . . ?
C20A C57B H57B 120.0 . . ?
C56A C57B H57B 120.0 . . ?
C42A C56A C57B 120.0 . . ?
C42A C56A N3A 120.8(7) . . ?
C57B C56A N3A 119.1(7) . . ?
C56A C42A C10A 120.0 . . ?
C56A C42A H42A 120.0 . . ?
C10A C42A H42A 120.0 . . ?
C4A C10A C42A 120.0 . . ?
C4A C10A H10A 120.0 . . ?
C42A C10A H10A 120.0 . . ?
C10A C4A C20A 120.0 . . ?
C10A C4A C14 125.5(9) . . ?
C20A C4A C14 114.4(9) . . ?
C24 C16A C11 107.6(16) . . ?
C24 C16A C20B 101.2(12) . . ?
C11 C16A C20B 102.9(12) . . ?
C24 C16A H16A 114.6 . . ?
C11 C16A H16A 114.6 . . ?
C20B C16A H16A 114.6 . . ?
N3A N2B C48 122.4(9) . . ?
N2A N3B O1B 125.0(8) . . ?
N2A N3B C50 115.0(6) . . ?
O1B N3B C50 119.6(6) . . ?
N3B N2A C56B 119.6(6) . . ?
O1A N3A N2B 117.8(14) . . ?
O1A N3A C56A 124.0(12) . . ?
N2B N3A C56A 117.7(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
C10B C4B C20B C57A 0.0 . . . . ?
C14 C4B C20B C57A -176.6(7) . . . . ?
C10B C4B C20B C16A 178.8(13) . . . . ?
C14 C4B C20B C16A 2.2(12) . . . . ?
C4B C20B C57A C56B 0.0 . . . . ?
C16A C20B C57A C56B -178.7(14) . . . . ?
C20B C57A C56B C42B 0.0 . . . . ?
C20B C57A C56B N2A 178.3(5) . . . . ?
C57A C56B C42B C10B 0.0 . . . . ?
N2A C56B C42B C10B -177.9(7) . . . . ?
C56B C42B C10B C4B 0.0 . . . . ?
C20B C4B C10B C42B 0.0 . . . . ?
C14 C4B C10B C42B 176.0(9) . . . . ?
C12B C1 C7 C15 -124.3(3) . . . . ?
C13 C1 C7 C15 124.4(2) . . . . ?
C12A C1 C7 C15 -123.7(4) . . . . ?
C12B C1 C7 C6 56.4(3) . . . . ?
C13 C1 C7 C6 -55.0(2) . . . . ?
C12A C1 C7 C6 56.9(4) . . . . ?
C12B C1 C13 C3 119.6(3) . . . . ?
C7 C1 C13 C3 -125.5(2) . . . . ?
C12A C1 C13 C3 128.1(4) . . . . ?
C12B C1 C13 C17 -59.3(3) . . . . ?
C7 C1 C13 C17 55.7(2) . . . . ?
C12A C1 C13 C17 -50.7(4) . . . . ?
C20B C4B C14 C9 53.5(5) . . . . ?
C10B C4B C14 C9 -122.8(5) . . . . ?
C20B C4B C14 C8 -57.6(5) . . . . ?
C10B C4B C14 C8 126.2(5) . . . . ?
C4A C14 C8 C24 57.0(6) . . . . ?
C9 C14 C8 C24 -56.8(2) . . . . ?
C4B C14 C8 C24 55.2(3) . . . . ?
C4A C14 C8 C19 -123.2(6) . . . . ?
C9 C14 C8 C19 123.1(2) . . . . ?
C4B C14 C8 C19 -124.9(3) . . . . ?
C4A C14 C9 C21 120.1(8) . . . . ?
C8 C14 C9 C21 -123.3(2) . . . . ?
C4B C14 C9 C21 127.2(4) . . . . ?
C4A C14 C9 C11 -60.4(8) . . . . ?
C8 C14 C9 C11 56.1(2) . . . . ?
C4B C14 C9 C11 -53.3(4) . . . . ?
C21 C9 C11 C25 0.0(3) . . . . ?
C14 C9 C11 C25 -179.54(18) . . . . ?
C21 C9 C11 C16B -175.0(16) . . . . ?
C14 C9 C11 C16B 5.5(16) . . . . ?
C21 C9 C11 C16A 176.1(9) . . . . ?
C14 C9 C11 C16A -3.4(10) . . . . ?
C17 C13 C3 C26 0.1(3) . . . . ?
C1 C13 C3 C26 -178.66(19) . . . . ?
C13 C1 C12B C18 57.2(4) . . . . ?
C7 C1 C12B C18 -55.4(4) . . . . ?
C13 C1 C12B C23 -127.9(4) . . . . ?
C7 C1 C12B C23 119.4(4) . . . . ?
C23 C12B C18 C34 0.0 . . . . ?
C1 C12B C18 C34 175.1(6) . . . . ?
C23 C12B C18 C5 -175.9(8) . . . . ?
C1 C12B C18 C5 -0.7(7) . . . . ?
C12B C18 C34 C50 0.0 . . . . ?
C5 C18 C34 C50 175.1(9) . . . . ?
C18 C34 C50 C38 0.0 . . . . ?
C18 C34 C50 N3B 178.4(4) . . . . ?
C34 C50 C38 C23 0.0 . . . . ?
N3B C50 C38 C23 -178.4(4) . . . . ?
C50 C38 C23 C12B 0.0 . . . . ?
C18 C12B C23 C38 0.0 . . . . ?
C1 C12B C23 C38 -174.6(6) . . . . ?
C19 C8 C24 C31 1.0(3) . . . . ?
C14 C8 C24 C31 -179.16(19) . . . . ?
C19 C8 C24 C16A -176.0(10) . . . . ?
C14 C8 C24 C16A 3.9(10) . . . . ?
C19 C8 C24 C16B 176.7(16) . . . . ?
C14 C8 C24 C16B -3.4(16) . . . . ?
C6 C7 C15 C29 0.2(3) . . . . ?
C1 C7 C15 C29 -179.0(2) . . . . ?
C12B C18 C5 C17 -54.5(8) . . . . ?
C34 C18 C5 C17 130.1(7) . . . . ?
C12B C18 C5 C6 52.6(11) . . . . ?
C34 C18 C5 C6 -122.8(7) . . . . ?
C25 C11 C16B C20A -118.2(16) . . . . ?
C9 C11 C16B C20A 56(3) . . . . ?
C25 C11 C16B C24 119.7(17) . . . . ?
C9 C11 C16B C24 -66.1(13) . . . . ?
C8 C24 C16B C20A -53(3) . . . . ?
C31 C24 C16B C20A 122.1(18) . . . . ?
C8 C24 C16B C11 65.4(14) . . . . ?
C31 C24 C16B C11 -119.6(16) . . . . ?
C3 C13 C17 C35 0.4(3) . . . . ?
C1 C13 C17 C35 179.4(2) . . . . ?
C3 C13 C17 C39 172.7(5) . . . . ?
C1 C13 C17 C39 -8.3(6) . . . . ?
C3 C13 C17 C5 -174.0(4) . . . . ?
C1 C13 C17 C5 5.0(4) . . . . ?
C18 C5 C17 C35 -122.0(6) . . . . ?
C6 C5 C17 C35 125.1(5) . . . . ?
C18 C5 C17 C13 52.0(7) . . . . ?
C6 C5 C17 C13 -60.9(5) . . . . ?
C24 C8 C19 C37 -2.0(3) . . . . ?
C14 C8 C19 C37 178.17(19) . . . . ?
C15 C7 C6 C27 -0.8(3) . . . . ?
C1 C7 C6 C27 178.5(2) . . . . ?
C15 C7 C6 C39 -175.0(9) . . . . ?
C1 C7 C6 C39 4.4(9) . . . . ?
C15 C7 C6 C5 176.9(5) . . . . ?
C1 C7 C6 C5 -3.7(5) . . . . ?
C18 C5 C6 C27 127.1(7) . . . . ?
C17 C5 C6 C27 -121.7(6) . . . . ?
C18 C5 C6 C7 -50.5(11) . . . . ?
C17 C5 C6 C7 60.7(4) . . . . ?
C11 C9 C21 C30 0.6(3) . . . . ?
C14 C9 C21 C30 -179.94(19) . . . . ?
C9 C11 C25 C28 -0.6(3) . . . . ?
C16B C11 C25 C28 173(2) . . . . ?
C16A C11 C25 C28 -176.4(11) . . . . ?
C13 C3 C26 C33 -0.3(3) . . . . ?
C39 C6 C27 C36 174.2(11) . . . . ?
C7 C6 C27 C36 0.6(4) . . . . ?
C5 C6 C27 C36 -176.8(6) . . . . ?
C13 C17 C35 C33 -0.8(4) . . . . ?
C39 C17 C35 C33 -172.0(7) . . . . ?
C5 C17 C35 C33 172.8(4) . . . . ?
C9 C21 C30 C28 -0.6(3) . . . . ?
C21 C30 C28 C25 0.0(4) . . . . ?
C11 C25 C28 C30 0.6(4) . . . . ?
C7 C15 C29 C36 0.7(4) . . . . ?
C8 C24 C31 C41 0.3(3) . . . . ?
C16A C24 C31 C41 177.0(11) . . . . ?
C16B C24 C31 C41 -174.2(19) . . . . ?
C3 C26 C33 C35 -0.1(4) . . . . ?
C17 C35 C33 C26 0.6(4) . . . . ?
C8 C19 C37 C41 1.7(3) . . . . ?
C15 C29 C36 C27 -0.9(4) . . . . ?
C6 C27 C36 C29 0.3(4) . . . . ?
C19 C37 C41 C31 -0.5(4) . . . . ?
C24 C31 C41 C37 -0.6(4) . . . . ?
C27 C6 C39 C17 -126.1(11) . . . . ?
C7 C6 C39 C17 47.8(8) . . . . ?
C27 C6 C39 C59 125.3(10) . . . . ?
C7 C6 C39 C59 -60.8(18) . . . . ?
C35 C17 C39 C6 125.9(9) . . . . ?
C13 C17 C39 C6 -45.9(8) . . . . ?
C35 C17 C39 C59 -125.4(8) . . . . ?
C13 C17 C39 C59 62.8(12) . . . . ?
C13 C1 C12A C52 -117.0(7) . . . . ?
C7 C1 C12A C52 132.5(8) . . . . ?
C13 C1 C12A C59 51.8(6) . . . . ?
C7 C1 C12A C59 -58.7(5) . . . . ?
C59 C12A C52 C60 0.0 . . . . ?
C1 C12A C52 C60 167.8(12) . . . . ?
C12A C52 C60 C48 0.0 . . . . ?
C52 C60 C48 N2B 175.5(9) . . . . ?
C52 C60 C48 C58 0.0 . . . . ?
N2B C48 C58 C59 -176.1(7) . . . . ?
C60 C48 C58 C59 0.0 . . . . ?
C48 C58 C59 C12A 0.0 . . . . ?
C48 C58 C59 C39 -174.7(16) . . . . ?
C52 C12A C59 C58 0.0 . . . . ?
C1 C12A C59 C58 -170.1(10) . . . . ?
C52 C12A C59 C39 175.1(15) . . . . ?
C1 C12A C59 C39 5.0(13) . . . . ?
C6 C39 C59 C58 -128.7(13) . . . . ?
C17 C39 C59 C58 113.2(13) . . . . ?
C6 C39 C59 C12A 56(2) . . . . ?
C17 C39 C59 C12A -61.7(13) . . . . ?
C11 C16B C20A C57B 125(2) . . . . ?
C24 C16B C20A C57B -120(2) . . . . ?
C11 C16B C20A C4A -62(3) . . . . ?
C24 C16B C20A C4A 53(3) . . . . ?
C4A C20A C57B C56A 0.0 . . . . ?
C16B C20A C57B C56A 173(3) . . . . ?
C20A C57B C56A C42A 0.0 . . . . ?
C20A C57B C56A N3A 176.2(10) . . . . ?
C57B C56A C42A C10A 0.0 . . . . ?
N3A C56A C42A C10A -176.1(10) . . . . ?
C56A C42A C10A C4A 0.0 . . . . ?
C42A C10A C4A C20A 0.0 . . . . ?
C42A C10A C4A C14 -177.5(16) . . . . ?
C57B C20A C4A C10A 0.0 . . . . ?
C16B C20A C4A C10A -174(2) . . . . ?
C57B C20A C4A C14 177.8(14) . . . . ?
C16B C20A C4A C14 4(2) . . . . ?
C9 C14 C4A C10A -127.0(8) . . . . ?
C8 C14 C4A C10A 119.5(9) . . . . ?
C9 C14 C4A C20A 55.4(9) . . . . ?
C8 C14 C4A C20A -58.1(9) . . . . ?
C8 C24 C16A C11 49.3(10) . . . . ?
C31 C24 C16A C11 -127.5(7) . . . . ?
C8 C24 C16A C20B -58.3(15) . . . . ?
C31 C24 C16A C20B 124.9(8) . . . . ?
C25 C11 C16A C24 126.5(7) . . . . ?
C9 C11 C16A C24 -49.5(10) . . . . ?
C25 C11 C16A C20B -127.2(8) . . . . ?
C9 C11 C16A C20B 56.8(16) . . . . ?
C57A C20B C16A C24 -126.5(10) . . . . ?
C4B C20B C16A C24 54.8(15) . . . . ?
C57A C20B C16A C11 122.4(11) . . . . ?
C4B C20B C16A C11 -56.4(16) . . . . ?
C60 C48 N2B N3A -3.5(10) . . . . ?
C58 C48 N2B N3A 172.3(6) . . . . ?
C38 C50 N3B N2A 168.6(3) . . . . ?
C34 C50 N3B N2A -9.8(5) . . . . ?
C38 C50 N3B O1B -17.3(8) . . . . ?
C34 C50 N3B O1B 164.3(7) . . . . ?
O1B N3B N2A C56B 3.7(9) . . . . ?
C50 N3B N2A C56B 177.4(4) . . . . ?
C42B C56B N2A N3B 7.1(8) . . . . ?
C57A C56B N2A N3B -171.0(4) . . . . ?
C48 N2B N3A O1A 6.7(13) . . . . ?
C48 N2B N3A C56A 178.8(7) . . . . ?
C42A C56A N3A O1A -9.1(14) . . . . ?
C57B C56A N3A O1A 174.7(11) . . . . ?
C42A C56A N3A N2B 179.3(7) . . . . ?
C57B C56A N3A N2B 3.2(9) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036

