# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mkf11se
_database_code_depnum_ccdc_archive 'CCDC 1478914'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-07-26 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         'C38 H32 N4 O2'
_chemical_formula_sum            'C38 H32 N4 O2'
_chemical_formula_weight         576.67

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   11.4777(5)
_cell_length_b                   15.9325(7)
_cell_length_c                   17.0968(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.233(2)
_cell_angle_gamma                90
_cell_volume                     3043.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      40.25
_exptl_crystal_description       red
_exptl_crystal_colour            block

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.844
_exptl_crystal_size_mid          0.744
_exptl_crystal_size_min          0.642
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_T_max  0.7485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'INCOATEC microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS with Photon 100'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_number            114976
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             11572
_reflns_number_gt                10158
_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       'Bruker Instrument Service v4.2.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0675P)²+0.6440P] 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         11572
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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_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
C1 C 1.00186(7) 0.33740(5) -0.00858(5) 0.01803(13) Uani 1 1 d . . . . .
C2 C 0.99254(7) 0.33342(6) -0.09111(5) 0.02177(15) Uani 1 1 d . . . . .
H2 H 0.9245 0.3558 -0.1275 0.026 Uiso 1 1 calc R U . . .
C3 C 1.08416(8) 0.29619(6) -0.11925(6) 0.02568(17) Uani 1 1 d . . . . .
H3 H 1.0800 0.2923 -0.1753 0.031 Uiso 1 1 calc R U . . .
C4 C 1.18158(9) 0.26492(6) -0.06413(7) 0.03024(19) Uani 1 1 d . . . . .
H4 H 1.2445 0.2403 -0.0840 0.036 Uiso 1 1 calc R U . . .
N5 N 1.19294(8) 0.26707(7) 0.01543(6) 0.0351(2) Uani 1 1 d . . . . .
C6 C 1.10378(8) 0.30276(7) 0.04223(6) 0.02815(18) Uani 1 1 d . . . . .
H6 H 1.1100 0.3047 0.0986 0.034 Uiso 1 1 calc R U . . .
C8 C 0.82864(7) 0.40759(5) 0.04649(5) 0.01723(13) Uani 1 1 d . . . . .
C7 C 0.90965(7) 0.37582(5) 0.02283(5) 0.01891(14) Uani 1 1 d . . . . .
C9 C 0.72981(6) 0.44618(5) 0.07059(4) 0.01475(12) Uani 1 1 d . . . . .
C10 C 0.69466(7) 0.52824(5) 0.04484(5) 0.01637(13) Uani 1 1 d . . . . .
H10 H 0.7362 0.5571 0.0109 0.020 Uiso 1 1 calc R U . . .
C11 C 0.60091(7) 0.56724(4) 0.06813(4) 0.01501(12) Uani 1 1 d . . . . .
H11 H 0.5791 0.6229 0.0508 0.018 Uiso 1 1 calc R U . . .
C12 C 0.53728(6) 0.52480(4) 0.11754(4) 0.01215(11) Uani 1 1 d . . . . .
N15 N 0.45069(6) 0.56588(4) 0.14778(4) 0.01330(11) Uani 1 1 d . . . . .
C14 C 0.66369(6) 0.40249(4) 0.11600(4) 0.01386(12) Uani 1 1 d . . . . .
H14 H 0.6859 0.3468 0.1328 0.017 Uiso 1 1 calc R U . . .
C13 C 0.56458(6) 0.43966(4) 0.13727(4) 0.01214(11) Uani 1 1 d . . . . .
C16 C 0.42102(6) 0.53399(4) 0.21589(4) 0.01332(12) Uani 1 1 d . . . . .
C18 C 0.48796(6) 0.39492(4) 0.18096(4) 0.01221(11) Uani 1 1 d . . . . .
C19 C 0.36814(7) 0.58535(5) 0.26518(5) 0.01783(13) Uani 1 1 d . . . . .
H19 H 0.3441 0.6408 0.2485 0.021 Uiso 1 1 calc R U . . .
C20 C 0.35103(7) 0.55590(5) 0.33740(5) 0.01963(14) Uani 1 1 d . . . . .
H20 H 0.3161 0.5915 0.3703 0.024 Uiso 1 1 calc R U . . .
C21 C 0.38466(7) 0.47362(5) 0.36327(5) 0.01644(13) Uani 1 1 d . . . . .
C22 C 0.42960(6) 0.42095(4) 0.31236(4) 0.01478(12) Uani 1 1 d . . . . .
H22 H 0.4501 0.3648 0.3285 0.018 Uiso 1 1 calc R U . . .
C23 C 0.37067(7) 0.44553(5) 0.43991(5) 0.01865(14) Uani 1 1 d . . . . .
C24 C 0.35447(7) 0.42502(5) 0.50443(5) 0.01919(14) Uani 1 1 d . . . . .
C25 C 0.32775(7) 0.40425(5) 0.57951(5) 0.01685(13) Uani 1 1 d . . . . .
C26 C 0.30777(7) 0.46680(5) 0.63204(5) 0.01990(14) Uani 1 1 d . . . . .
H26 H 0.3151 0.5244 0.6196 0.024 Uiso 1 1 calc R U . . .
C27 C 0.27706(8) 0.44319(7) 0.70266(5) 0.02592(17) Uani 1 1 d . . . . .
H27 H 0.2625 0.4843 0.7395 0.031 Uiso 1 1 calc R U . . .
C28 C 0.26796(8) 0.35826(7) 0.71857(5) 0.02942(19) Uani 1 1 d . . . . .
H28 H 0.2472 0.3427 0.7673 0.035 Uiso 1 1 calc R U . . .
N29 N 0.28661(8) 0.29734(6) 0.66950(5) 0.02986(17) Uani 1 1 d . . . . .
C30 C 0.31608(8) 0.32059(6) 0.60157(5) 0.02332(15) Uani 1 1 d . . . . .
H30 H 0.3300 0.2778 0.5661 0.028 Uiso 1 1 calc R U . . .
C31 C 0.40199(6) 0.64755(4) 0.11502(4) 0.01490(12) Uani 1 1 d . . . . .
H31A H 0.3178 0.6512 0.1199 0.018 Uiso 1 1 calc R U . . .
H31B H 0.4012 0.6486 0.0570 0.018 Uiso 1 1 calc R U . . .
C32 C 0.46793(7) 0.72566(4) 0.15387(5) 0.01635(13) Uani 1 1 d . . . . .
H32A H 0.5481 0.7287 0.1417 0.020 Uiso 1 1 calc R U . . .
H32B H 0.4784 0.7229 0.2129 0.020 Uiso 1 1 calc R U . . .
C33 C 0.39503(7) 0.80329(5) 0.12089(5) 0.01858(13) Uani 1 1 d . . . . .
H33A H 0.3131 0.7968 0.1295 0.022 Uiso 1 1 calc R U . . .
H33B H 0.3885 0.8061 0.0622 0.022 Uiso 1 1 calc R U . . .
C34 C 0.44664(8) 0.88628(5) 0.15836(5) 0.02089(14) Uani 1 1 d . . . . .
H34A H 0.5311 0.8905 0.1542 0.025 Uiso 1 1 calc R U . . .
H34B H 0.4020 0.9330 0.1269 0.025 Uiso 1 1 calc R U . . .
C35 C 0.44170(10) 0.89669(6) 0.24605(5) 0.02628(17) Uani 1 1 d . . . . .
H35A H 0.3600 0.8829 0.2519 0.032 Uiso 1 1 calc R U . . .
H35B H 0.4978 0.8563 0.2791 0.032 Uiso 1 1 calc R U . . .
C36 C 0.47356(10) 0.98496(6) 0.27778(6) 0.0316(2) Uani 1 1 d . . . . .
H36A H 0.5557 0.9982 0.2744 0.047 Uiso 1 1 calc R U . . .
H36B H 0.4673 0.9883 0.3339 0.047 Uiso 1 1 calc R U . . .
H36C H 0.4183 1.0253 0.2455 0.047 Uiso 1 1 calc R U . . .
C37 C 0.45442(6) 0.31216(4) 0.16978(4) 0.01361(12) Uani 1 1 d . . . . .
C38 C 0.37033(7) 0.27702(5) 0.21108(5) 0.01682(13) Uani 1 1 d . . . . .
N39 N 0.30010(7) 0.24782(5) 0.24159(5) 0.02511(15) Uani 1 1 d . . . . .
C40 C 0.48360(6) 0.25343(4) 0.10901(4) 0.01349(12) Uani 1 1 d . . . . .
O41 O 0.50765(6) 0.27232(4) 0.04617(3) 0.01841(11) Uani 1 1 d . . . . .
O42 O 0.47699(5) 0.17410(3) 0.13405(3) 0.01702(11) Uani 1 1 d . . . . .
C43 C 0.49899(7) 0.10868(4) 0.08024(5) 0.01698(13) Uani 1 1 d . . . . .
H43A H 0.5248 0.0569 0.1115 0.020 Uiso 1 1 calc R U . . .
H43B H 0.5647 0.1264 0.0552 0.020 Uiso 1 1 calc R U . . .
C44 C 0.38930(8) 0.09012(6) 0.01549(6) 0.02444(16) Uani 1 1 d . . . . .
H44A H 0.3695 0.1391 -0.0197 0.037 Uiso 1 1 calc R U . . .
H44B H 0.3221 0.0774 0.0401 0.037 Uiso 1 1 calc R U . . .
H44C H 0.4048 0.0418 -0.0161 0.037 Uiso 1 1 calc R U . . .
C17 C 0.44531(6) 0.44904(4) 0.23778(4) 0.01274(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3918(12) . ?
C1 C6 1.4009(12) . ?
C1 C7 1.4295(10) . ?
C2 C3 1.3860(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3799(15) . ?
C3 H3 0.9500 . ?
C4 N5 1.3370(15) . ?
C4 H4 0.9500 . ?
N5 C6 1.3398(12) . ?
C6 H6 0.9500 . ?
C8 C7 1.2069(10) . ?
C8 C9 1.4313(10) . ?
C9 C14 1.3903(10) . ?
C9 C10 1.4087(10) . ?
C10 C11 1.3778(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.4095(10) . ?
C11 H11 0.9500 . ?
C12 N15 1.3852(9) . ?
C12 C13 1.4155(9) . ?
N15 C16 1.3826(9) . ?
N15 C31 1.4751(9) . ?
C14 C13 1.4022(9) . ?
C14 H14 0.9500 . ?
C13 C18 1.4629(9) . ?
C16 C19 1.4079(10) . ?
C16 C17 1.4148(10) . ?
C18 C37 1.3746(9) . ?
C18 C17 1.4644(9) . ?
C19 C20 1.3763(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.4090(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.3904(10) . ?
C21 C23 1.4280(11) . ?
C22 C17 1.4015(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.2051(11) . ?
C24 C25 1.4254(11) . ?
C25 C26 1.3952(11) . ?
C25 C30 1.4000(12) . ?
C26 C27 1.3849(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.3889(16) . ?
C27 H27 0.9500 . ?
C28 N29 1.3320(15) . ?
C28 H28 0.9500 . ?
N29 C30 1.3342(12) . ?
C30 H30 0.9500 . ?
C31 C32 1.5273(10) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.5271(10) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5283(11) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5223(12) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5215(13) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.4338(10) . ?
C37 C40 1.4922(10) . ?
C38 N39 1.1536(10) . ?
C40 O41 1.2070(9) . ?
C40 O42 1.3421(8) . ?
O42 C43 1.4502(9) . ?
C43 C44 1.5033(12) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.05(7) . . ?
C2 C1 C7 120.57(7) . . ?
C6 C1 C7 121.39(8) . . ?
C3 C2 C1 118.89(8) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 118.56(9) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
N5 C4 C3 124.10(8) . . ?
N5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 N5 C6 117.04(9) . . ?
N5 C6 C1 123.36(9) . . ?
N5 C6 H6 118.3 . . ?
C1 C6 H6 118.3 . . ?
C7 C8 C9 177.22(9) . . ?
C8 C7 C1 177.40(9) . . ?
C14 C9 C10 119.03(6) . . ?
C14 C9 C8 121.04(7) . . ?
C10 C9 C8 119.86(7) . . ?
C11 C10 C9 120.99(7) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.20(7) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
N15 C12 C11 120.77(6) . . ?
N15 C12 C13 120.16(6) . . ?
C11 C12 C13 119.06(6) . . ?
C16 N15 C12 118.48(6) . . ?
C16 N15 C31 119.93(6) . . ?
C12 N15 C31 121.13(6) . . ?
C9 C14 C13 120.82(6) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C13 C12 119.43(6) . . ?
C14 C13 C18 123.01(6) . . ?
C12 C13 C18 117.55(6) . . ?
N15 C16 C19 120.91(6) . . ?
N15 C16 C17 120.17(6) . . ?
C19 C16 C17 118.92(6) . . ?
C37 C18 C13 125.33(6) . . ?
C37 C18 C17 122.11(6) . . ?
C13 C18 C17 112.52(6) . . ?
C20 C19 C16 120.56(7) . . ?
C20 C19 H19 119.7 . . ?
C16 C19 H19 119.7 . . ?
C19 C20 C21 120.91(7) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 118.64(7) . . ?
C22 C21 C23 121.40(7) . . ?
C20 C21 C23 119.95(7) . . ?
C21 C22 C17 121.35(7) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C24 C23 C21 176.61(9) . . ?
C23 C24 C25 175.94(9) . . ?
C26 C25 C30 117.82(7) . . ?
C26 C25 C24 120.99(7) . . ?
C30 C25 C24 121.15(7) . . ?
C27 C26 C25 118.64(8) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C26 C27 C28 118.75(8) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
N29 C28 C27 123.81(8) . . ?
N29 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
C28 N29 C30 117.08(9) . . ?
N29 C30 C25 123.91(9) . . ?
N29 C30 H30 118.0 . . ?
C25 C30 H30 118.0 . . ?
N15 C31 C32 116.53(6) . . ?
N15 C31 H31A 108.2 . . ?
C32 C31 H31A 108.2 . . ?
N15 C31 H31B 108.2 . . ?
C32 C31 H31B 108.2 . . ?
H31A C31 H31B 107.3 . . ?
C31 C32 C33 108.92(6) . . ?
C31 C32 H32A 109.9 . . ?
C33 C32 H32A 109.9 . . ?
C31 C32 H32B 109.9 . . ?
C33 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C32 C33 C34 114.76(7) . . ?
C32 C33 H33A 108.6 . . ?
C34 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
C34 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C35 C34 C33 114.14(7) . . ?
C35 C34 H34A 108.7 . . ?
C33 C34 H34A 108.7 . . ?
C35 C34 H34B 108.7 . . ?
C33 C34 H34B 108.7 . . ?
H34A C34 H34B 107.6 . . ?
C36 C35 C34 113.07(8) . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C34 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C18 C37 C38 120.32(6) . . ?
C18 C37 C40 126.73(6) . . ?
C38 C37 C40 112.44(6) . . ?
N39 C38 C37 177.46(9) . . ?
O41 C40 O42 124.05(6) . . ?
O41 C40 C37 126.64(6) . . ?
O42 C40 C37 109.29(6) . . ?
C40 O42 C43 116.34(6) . . ?
O42 C43 C44 111.74(6) . . ?
O42 C43 H43A 109.3 . . ?
C44 C43 H43A 109.3 . . ?
O42 C43 H43B 109.3 . . ?
C44 C43 H43B 109.3 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C22 C17 C16 119.18(6) . . ?
C22 C17 C18 123.20(6) . . ?
C16 C17 C18 117.61(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 C3 -0.45(13) . . . . ?
C7 C1 C2 C3 179.56(8) . . . . ?
C1 C2 C3 C4 -0.39(13) . . . . ?
C2 C3 C4 N5 0.99(16) . . . . ?
C3 C4 N5 C6 -0.65(17) . . . . ?
C4 N5 C6 C1 -0.28(17) . . . . ?
C2 C1 C6 N5 0.82(15) . . . . ?
C7 C1 C6 N5 -179.19(10) . . . . ?
C14 C9 C10 C11 4.04(11) . . . . ?
C8 C9 C10 C11 -179.07(7) . . . . ?
C9 C10 C11 C12 -0.89(11) . . . . ?
C10 C11 C12 N15 173.67(7) . . . . ?
C10 C11 C12 C13 -5.14(11) . . . . ?
C11 C12 N15 C16 -157.63(7) . . . . ?
C13 C12 N15 C16 21.18(10) . . . . ?
C11 C12 N15 C31 14.57(10) . . . . ?
C13 C12 N15 C31 -166.62(6) . . . . ?
C10 C9 C14 C13 -1.08(11) . . . . ?
C8 C9 C14 C13 -177.93(7) . . . . ?
C9 C14 C13 C12 -4.92(10) . . . . ?
C9 C14 C13 C18 176.40(7) . . . . ?
N15 C12 C13 C14 -170.83(6) . . . . ?
C11 C12 C13 C14 8.00(10) . . . . ?
N15 C12 C13 C18 7.92(10) . . . . ?
C11 C12 C13 C18 -173.25(6) . . . . ?
C12 N15 C16 C19 157.65(7) . . . . ?
C31 N15 C16 C19 -14.64(10) . . . . ?
C12 N15 C16 C17 -21.35(10) . . . . ?
C31 N15 C16 C17 166.35(6) . . . . ?
C14 C13 C18 C37 -38.13(11) . . . . ?
C12 C13 C18 C37 143.17(7) . . . . ?
C14 C13 C18 C17 143.94(7) . . . . ?
C12 C13 C18 C17 -34.77(9) . . . . ?
N15 C16 C19 C20 -172.75(7) . . . . ?
C17 C16 C19 C20 6.26(11) . . . . ?
C16 C19 C20 C21 -0.71(13) . . . . ?
C19 C20 C21 C22 -3.49(12) . . . . ?
C19 C20 C21 C23 177.40(8) . . . . ?
C20 C21 C22 C17 2.06(11) . . . . ?
C23 C21 C22 C17 -178.84(7) . . . . ?
C30 C25 C26 C27 -0.30(11) . . . . ?
C24 C25 C26 C27 177.25(7) . . . . ?
C25 C26 C27 C28 0.31(12) . . . . ?
C26 C27 C28 N29 -0.30(14) . . . . ?
C27 C28 N29 C30 0.25(14) . . . . ?
C28 N29 C30 C25 -0.24(14) . . . . ?
C26 C25 C30 N29 0.27(13) . . . . ?
C24 C25 C30 N29 -177.27(8) . . . . ?
C16 N15 C31 C32 82.83(8) . . . . ?
C12 N15 C31 C32 -89.25(8) . . . . ?
N15 C31 C32 C33 -171.85(6) . . . . ?
C31 C32 C33 C34 176.47(6) . . . . ?
C32 C33 C34 C35 -68.34(10) . . . . ?
C33 C34 C35 C36 -170.20(8) . . . . ?
C13 C18 C37 C38 -174.44(7) . . . . ?
C17 C18 C37 C38 3.30(11) . . . . ?
C13 C18 C37 C40 -3.34(12) . . . . ?
C17 C18 C37 C40 174.41(7) . . . . ?
C18 C37 C40 O41 -24.28(12) . . . . ?
C38 C37 C40 O41 147.41(8) . . . . ?
C18 C37 C40 O42 156.90(7) . . . . ?
C38 C37 C40 O42 -31.41(9) . . . . ?
O41 C40 O42 C43 -0.89(11) . . . . ?
C37 C40 O42 C43 177.97(6) . . . . ?
C40 O42 C43 C44 -82.06(8) . . . . ?
C21 C22 C17 C16 3.47(11) . . . . ?
C21 C22 C17 C18 -177.58(7) . . . . ?
N15 C16 C17 C22 171.45(7) . . . . ?
C19 C16 C17 C22 -7.57(10) . . . . ?
N15 C16 C17 C18 -7.56(10) . . . . ?
C19 C16 C17 C18 173.41(7) . . . . ?
C37 C18 C17 C22 37.65(10) . . . . ?
C13 C18 C17 C22 -144.34(7) . . . . ?
C37 C18 C17 C16 -143.39(7) . . . . ?
C13 C18 C17 C16 34.62(9) . . . . ?

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeCN
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1478915'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-07-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H32 D8 N4 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         704.87

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7141(3)
_cell_length_b                   13.7175(4)
_cell_length_c                   13.8642(4)
_cell_angle_alpha                92.206(2)
_cell_angle_beta                 97.198(2)
_cell_angle_gamma                98.744(2)
_cell_volume                     1808.46(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      3.2654
_cell_measurement_theta_max      74.5379
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense red'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfucus sealed tube'
_diffrn_source_type              'INCOATEC microfocus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            21094
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         74.61
_diffrn_reflns_theta_full        74.61
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             7238
_reflns_number_gt                5809
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1183
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.058
_refine_ls_number_reflns         7238
_refine_ls_number_parameters     499
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+1.1070P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
D D 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'

_computing_data_collection       'Bruker Instrument Service v4.2.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.26179(16) 0.43816(11) 0.40127(12) 0.0150(3) Uani d . . . 1.0 . .
C C2 0.20646(16) 0.43670(12) 0.30346(12) 0.0169(3) Uani d . . . 1.0 . .
C C3 0.13653(17) 0.51192(12) 0.25974(12) 0.0193(3) Uani d . . . 1.0 . .
C C4 0.19860(16) 0.34893(12) 0.23531(12) 0.0170(3) Uani d . . . 1.0 . .
C C5 0.19696(17) 0.30766(12) 0.06555(12) 0.0187(3) Uani d . . . 1.0 . .
C C6 0.27909(17) 0.23309(12) 0.06890(12) 0.0203(3) Uani d . . . 1.0 . .
H H6 0.3414 0.226 0.1258 0.024 Uiso calc U . R 1.0 . .
C C7 0.26821(18) 0.16914(13) -0.01257(13) 0.0218(4) Uani d . . . 1.0 . .
H H7 0.3229 0.1173 -0.0113 0.026 Uiso calc U . R 1.0 . .
C C8 0.17818(18) 0.18017(13) -0.09605(13) 0.0228(4) Uani d . . . 1.0 . .
H H8 0.1702 0.1354 -0.1512 0.027 Uiso calc U . R 1.0 . .
C C9 0.09987(18) 0.25680(13) -0.09857(13) 0.0231(4) Uani d . . . 1.0 . .
H H9 0.0398 0.2654 -0.1561 0.028 Uiso calc U . R 1.0 . .
C C10 0.10889(18) 0.32089(13) -0.01733(13) 0.0213(4) Uani d . . . 1.0 . .
H H10 0.0551 0.3733 -0.0188 0.026 Uiso calc U . R 1.0 . .
C C11 0.36327(16) 0.37373(11) 0.43198(12) 0.0153(3) Uani d . . . 1.0 . .
C C12 0.44417(16) 0.33691(12) 0.36607(12) 0.0169(3) Uani d . . . 1.0 . .
H H12 0.4391 0.3601 0.3022 0.02 Uiso calc U . R 1.0 . .
C C13 0.53092(16) 0.26816(12) 0.39059(12) 0.0185(3) Uani d . . . 1.0 . .
C C14 0.54454(17) 0.23927(12) 0.48729(13) 0.0207(4) Uani d . . . 1.0 . .
H H14 0.6023 0.1912 0.5053 0.025 Uiso calc U . R 1.0 . .
C C15 0.47608(17) 0.27921(12) 0.55558(12) 0.0199(3) Uani d . . . 1.0 . .
H H15 0.49 0.2608 0.621 0.024 Uiso calc U . R 1.0 . .
C C16 0.38455(16) 0.34780(12) 0.52968(12) 0.0168(3) Uani d . . . 1.0 . .
C C17 0.32748(17) 0.35352(12) 0.69805(12) 0.0179(3) Uani d . . . 1.0 . .
H H17A 0.3326 0.282 0.6945 0.022 Uiso calc U . R 1.0 . .
H H17B 0.2417 0.3625 0.7269 0.022 Uiso calc U . R 1.0 . .
C C18 0.45593(17) 0.40763(12) 0.76423(12) 0.0198(3) Uani d . . . 1.0 . .
H H18A 0.5411 0.4038 0.7327 0.024 Uiso calc U . R 1.0 . .
H H18B 0.4467 0.4782 0.7729 0.024 Uiso calc U . R 1.0 . .
C C19 0.47313(18) 0.36421(13) 0.86347(13) 0.0225(4) Uani d . . . 1.0 . .
H H19A 0.4746 0.2925 0.8543 0.027 Uiso calc U . R 1.0 . .
H H19B 0.3909 0.3726 0.8967 0.027 Uiso calc U . R 1.0 . .
C C20 0.60664(17) 0.41192(13) 0.92821(12) 0.0217(4) Uani d . . . 1.0 . .
H H20A 0.6882 0.4078 0.8929 0.026 Uiso calc U . R 1.0 . .
H H20B 0.6019 0.4827 0.9411 0.026 Uiso calc U . R 1.0 . .
C C21 0.6300(2) 0.36432(14) 1.02466(14) 0.0302(4) Uani d . . . 1.0 . .
H H21A 0.5523 0.3732 1.0623 0.036 Uiso calc U . R 1.0 . .
H H21B 0.627 0.2925 1.0118 0.036 Uiso calc U . R 1.0 . .
C C22 0.7681(2) 0.40635(17) 1.08536(14) 0.0342(5) Uani d . . . 1.0 . .
H H22A 0.8456 0.3988 1.0482 0.051 Uiso calc U . R 1.0 . .
H H22B 0.7787 0.3709 1.1452 0.051 Uiso calc U . R 1.0 . .
H H22C 0.7694 0.4766 1.102 0.051 Uiso calc U . R 1.0 . .
C C23 0.60295(17) 0.22675(12) 0.31885(13) 0.0194(3) Uani d . . . 1.0 . .
C C24 0.66037(17) 0.19019(12) 0.25847(12) 0.0196(3) Uani d . . . 1.0 . .
C C25 0.73371(18) 0.15027(12) 0.18661(12) 0.0194(3) Uani d . . . 1.0 . .
C C26 0.87722(19) 0.14654(13) 0.20423(14) 0.0255(4) Uani d . . . 1.0 . .
H H26 0.9293 0.1686 0.2658 0.031 Uiso calc U . R 1.0 . .
C C27 0.9425(2) 0.11026(14) 0.13083(15) 0.0297(4) Uani d . . . 1.0 . .
H H27 1.0402 0.1072 0.1409 0.036 Uiso calc U . R 1.0 . .
C C28 0.8634(2) 0.07865(14) 0.04296(15) 0.0298(4) Uani d . . . 1.0 . .
H H28 0.9097 0.0549 -0.0074 0.036 Uiso calc U . R 1.0 . .
C C29 0.6633(2) 0.11467(14) 0.09547(14) 0.0281(4) Uani d . . . 1.0 . .
H H29 0.5651 0.1156 0.0834 0.034 Uiso calc U . R 1.0 . .
C C30 0.22563(16) 0.49885(12) 0.47979(12) 0.0159(3) Uani d . . . 1.0 . .
C C31 0.15745(16) 0.58151(12) 0.46426(12) 0.0172(3) Uani d . . . 1.0 . .
H H31 0.1435 0.6037 0.4002 0.021 Uiso calc U . R 1.0 . .
C C32 0.10989(16) 0.63178(12) 0.53881(12) 0.0181(3) Uani d . . . 1.0 . .
C C33 0.13180(16) 0.59957(12) 0.63364(12) 0.0185(3) Uani d . . . 1.0 . .
H H33 0.099 0.6329 0.6854 0.022 Uiso calc U . R 1.0 . .
C C34 0.19969(17) 0.52094(12) 0.65228(12) 0.0182(3) Uani d . . . 1.0 . .
H H34 0.2138 0.5006 0.717 0.022 Uiso calc U . R 1.0 . .
C C35 0.24945(16) 0.46905(12) 0.57703(12) 0.0161(3) Uani d . . . 1.0 . .
C C36 0.03729(17) 0.71375(12) 0.51979(12) 0.0195(3) Uani d . . . 1.0 . .
C C37 -0.02835(17) 0.78023(12) 0.50481(12) 0.0202(3) Uani d . . . 1.0 . .
C C38 -0.10953(17) 0.85701(12) 0.48245(12) 0.0197(3) Uani d . . . 1.0 . .
C C39 -0.1870(2) 0.89500(14) 0.54879(14) 0.0264(4) Uani d . . . 1.0 . .
H H39 -0.185 0.871 0.6122 0.032 Uiso calc U . R 1.0 A 1
N N40 -0.1939(2) 0.96428(14) 0.36333(15) 0.0429(6) Uani d . P . 0.694(19) B 1
C C40 -0.2656(2) 0.96654(14) 0.52308(15) 0.0372(5) Uani d . P . 0.694(19) B 1
H H40 -0.3183 0.9933 0.5679 0.045 Uiso calc U P R 0.694(19) B 1
C C40A -0.1939(2) 0.96428(14) 0.36333(15) 0.0429(6) Uani d . P . 0.306(19) B 2
H H40A -0.1978 0.9882 0.2998 0.052 Uiso calc U P R 0.306(19) B 2
N N40A -0.2656(2) 0.96654(14) 0.52308(15) 0.0372(5) Uani d . P . 0.306(19) B 2
C C41 -0.2663(3) 0.99881(15) 0.43052(18) 0.0433(6) Uani d . . . 1.0 . .
H H41 -0.3212 1.0486 0.4127 0.052 Uiso calc U . R 1.0 B 1
C C42 -0.1159(2) 0.89456(14) 0.39024(14) 0.0301(4) Uani d . . . 1.0 . .
H H42 -0.0629 0.8698 0.3445 0.036 Uiso calc U . R 1.0 B 1
C C43 0.5476(3) 0.0727(2) 0.7817(2) 0.0595(8) Uani d . . . 1.0 . .
D D43A 0.4524 0.0353 0.7608 0.071 Uiso calc U P R 0.560(16) C 3
D D43B 0.5507 0.1088 0.8454 0.071 Uiso calc U P R 0.560(16) C 3
D D43C 0.4614 0.0363 0.7428 0.071 Uiso calc U P R 0.440(16) C 4
D D43D 0.5273 0.08 0.8496 0.071 Uiso calc U P R 0.440(16) C 4
C C44 0.6613(3) 0.00889(17) 0.78114(17) 0.0453(6) Uani d . . . 1.0 . .
D D44A 0.6378 -0.0426 0.7271 0.054 Uiso calc U . R 1.0 . .
D D44B 0.6758 -0.0233 0.8435 0.054 Uiso calc U . R 1.0 . .
C C45 0.7911(3) 0.08231(19) 0.76694(18) 0.0527(7) Uani d . . D 1.0 . .
D D45A 0.8499 0.1015 0.8304 0.063 Uiso calc U P R 0.560(16) C 3
D D45B 0.8479 0.0517 0.7234 0.063 Uiso calc U P R 0.560(16) C 3
D D45C 0.8225 0.0709 0.7028 0.063 Uiso calc U P R 0.440(16) C 4
D D45D 0.8699 0.081 0.8194 0.063 Uiso calc U P R 0.440(16) C 4
N N1 0.31622(14) 0.38888(10) 0.59856(10) 0.0165(3) Uani d . . . 1.0 . .
N N2 0.08039(17) 0.56996(12) 0.22057(11) 0.0268(3) Uani d . . . 1.0 . .
N N3 0.72496(19) 0.07936(13) 0.02405(12) 0.0345(4) Uani d . . . 1.0 . .
O O1 0.18103(12) 0.26394(8) 0.25569(8) 0.0209(3) Uani d . . . 1.0 . .
O O2 0.20802(13) 0.37846(9) 0.14325(8) 0.0231(3) Uani d . . . 1.0 . .
O O3 0.5993(6) 0.1381(6) 0.7062(7) 0.057(2) Uani d . P . 0.560(16) C 3
C C46 0.7465(7) 0.1664(6) 0.7255(8) 0.056(2) Uani d . P D 0.560(16) C 3
D D46A 0.7878 0.1809 0.6649 0.067 Uiso calc U P R 0.560(16) C 3
D D46B 0.7719 0.2251 0.7717 0.067 Uiso calc U P R 0.560(16) C 3
O O3A 0.5720(7) 0.1670(5) 0.7470(7) 0.0444(17) Uani d . P . 0.440(16) C 4
C C46A 0.7236(7) 0.1864(5) 0.7737(8) 0.042(2) Uani d . P D 0.440(16) C 4
D D46C 0.7463 0.2167 0.8409 0.05 Uiso calc U P R 0.440(16) C 4
D D46D 0.766 0.2337 0.7294 0.05 Uiso calc U P R 0.440(16) C 4


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.393(2) ?
C1 C30 . 1.455(2) ?
C1 C11 . 1.457(2) ?
C2 C3 . 1.432(2) ?
C2 C4 . 1.488(2) ?
C3 N2 . 1.148(2) ?
C4 O1 . 1.202(2) ?
C4 O2 . 1.3635(19) ?
C5 C10 . 1.379(2) ?
C5 C6 . 1.388(2) ?
C5 O2 . 1.405(2) ?
C6 C7 . 1.386(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.388(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.387(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.387(2) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C12 . 1.404(2) ?
C11 C16 . 1.412(2) ?
C12 C13 . 1.382(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.409(2) ?
C13 C23 . 1.433(2) ?
C14 C15 . 1.367(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.416(2) ?
C15 H15 . 0.95 ?
C16 N1 . 1.379(2) ?
C17 N1 . 1.476(2) ?
C17 C18 . 1.526(2) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.520(2) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.524(2) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 C21 . 1.517(2) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 C22 . 1.511(3) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 C24 . 1.197(2) ?
C24 C25 . 1.433(2) ?
C25 C29 . 1.392(3) ?
C25 C26 . 1.394(2) ?
C26 C27 . 1.380(2) ?
C26 H26 . 0.95 ?
C27 C28 . 1.373(3) ?
C27 H27 . 0.95 ?
C28 N3 . 1.339(3) ?
C28 H28 . 0.95 ?
C29 N3 . 1.332(2) ?
C29 H29 . 0.95 ?
C30 C31 . 1.408(2) ?
C30 C35 . 1.425(2) ?
C31 C32 . 1.385(2) ?
C31 H31 . 0.95 ?
C32 C33 . 1.404(2) ?
C32 C36 . 1.431(2) ?
C33 C34 . 1.364(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.415(2) ?
C34 H34 . 0.95 ?
C35 N1 . 1.383(2) ?
C36 C37 . 1.200(2) ?
C37 C38 . 1.430(2) ?
C38 C39 . 1.392(2) ?
C38 C42 . 1.394(3) ?
C39 N40A . 1.364(3) ?
C39 C40 . 1.364(3) ?
C39 H39 . 0.95 ?
N40 C42 . 1.343(3) ?
N40 C41 . 1.348(3) ?
C40 C41 . 1.373(3) ?
C40 H40 . 0.95 ?
C40A C42 . 1.343(3) ?
C40A C41 . 1.348(3) ?
C40A H40A . 0.95 ?
N40A C41 . 1.373(3) ?
C41 H41 . 0.95 ?
C42 H42 . 0.95 ?
C43 O3A . 1.394(6) ?
C43 O3 . 1.490(6) ?
C43 C44 . 1.511(4) ?
C43 D43A . 0.99 ?
C43 D43B . 0.99 ?
C43 D43C . 0.99 ?
C43 D43D . 0.99 ?
C44 C45 . 1.528(3) ?
C44 D44A . 0.99 ?
C44 D44B . 0.99 ?
C45 C46 . 1.411(6) ?
C45 C46A . 1.663(8) ?
C45 D45A . 0.99 ?
C45 D45B . 0.99 ?
C45 D45C . 0.99 ?
C45 D45D . 0.99 ?
O3 C46 . 1.412(7) ?
C46 D46A . 0.99 ?
C46 D46B . 0.99 ?
O3A C46A . 1.454(9) ?
C46A D46C . 0.99 ?
C46A D46D . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C30 . . 125.58(14) ?
C2 C1 C11 . . 119.79(14) ?
C30 C1 C11 . . 114.62(14) ?
C1 C2 C3 . . 125.05(15) ?
C1 C2 C4 . . 122.30(14) ?
C3 C2 C4 . . 112.24(14) ?
N2 C3 C2 . . 176.81(18) ?
O1 C4 O2 . . 123.89(15) ?
O1 C4 C2 . . 126.26(15) ?
O2 C4 C2 . . 109.79(13) ?
C10 C5 C6 . . 121.57(16) ?
C10 C5 O2 . . 116.47(15) ?
C6 C5 O2 . . 121.75(15) ?
C7 C6 C5 . . 118.59(16) ?
C7 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
C6 C7 C8 . . 120.65(16) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C9 C8 C7 . . 119.73(16) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 120.24(16) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C5 C10 C9 . . 119.19(16) ?
C5 C10 H10 . . 120.4 ?
C9 C10 H10 . . 120.4 ?
C12 C11 C16 . . 118.08(14) ?
C12 C11 C1 . . 121.24(14) ?
C16 C11 C1 . . 120.67(14) ?
C13 C12 C11 . . 122.45(15) ?
C13 C12 H12 . . 118.8 ?
C11 C12 H12 . . 118.8 ?
C12 C13 C14 . . 118.12(15) ?
C12 C13 C23 . . 120.56(15) ?
C14 C13 C23 . . 121.31(15) ?
C15 C14 C13 . . 121.13(15) ?
C15 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
C14 C15 C16 . . 120.59(16) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
N1 C16 C11 . . 120.02(14) ?
N1 C16 C15 . . 120.75(15) ?
C11 C16 C15 . . 119.22(15) ?
N1 C17 C18 . . 112.75(13) ?
N1 C17 H17A . . 109.0 ?
C18 C17 H17A . . 109.0 ?
N1 C17 H17B . . 109.0 ?
C18 C17 H17B . . 109.0 ?
H17A C17 H17B . . 107.8 ?
C19 C18 C17 . . 112.03(14) ?
C19 C18 H18A . . 109.2 ?
C17 C18 H18A . . 109.2 ?
C19 C18 H18B . . 109.2 ?
C17 C18 H18B . . 109.2 ?
H18A C18 H18B . . 107.9 ?
C18 C19 C20 . . 113.03(14) ?
C18 C19 H19A . . 109.0 ?
C20 C19 H19A . . 109.0 ?
C18 C19 H19B . . 109.0 ?
C20 C19 H19B . . 109.0 ?
H19A C19 H19B . . 107.8 ?
C21 C20 C19 . . 113.44(14) ?
C21 C20 H20A . . 108.9 ?
C19 C20 H20A . . 108.9 ?
C21 C20 H20B . . 108.9 ?
C19 C20 H20B . . 108.9 ?
H20A C20 H20B . . 107.7 ?
C22 C21 C20 . . 113.37(16) ?
C22 C21 H21A . . 108.9 ?
C20 C21 H21A . . 108.9 ?
C22 C21 H21B . . 108.9 ?
C20 C21 H21B . . 108.9 ?
H21A C21 H21B . . 107.7 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C24 C23 C13 . . 178.33(18) ?
C23 C24 C25 . . 177.46(18) ?
C29 C25 C26 . . 117.46(16) ?
C29 C25 C24 . . 120.67(16) ?
C26 C25 C24 . . 121.87(16) ?
C27 C26 C25 . . 118.98(17) ?
C27 C26 H26 . . 120.5 ?
C25 C26 H26 . . 120.5 ?
C28 C27 C26 . . 118.74(18) ?
C28 C27 H27 . . 120.6 ?
C26 C27 H27 . . 120.6 ?
N3 C28 C27 . . 123.91(18) ?
N3 C28 H28 . . 118.0 ?
C27 C28 H28 . . 118.0 ?
N3 C29 C25 . . 124.15(17) ?
N3 C29 H29 . . 117.9 ?
C25 C29 H29 . . 117.9 ?
C31 C30 C35 . . 117.68(14) ?
C31 C30 C1 . . 123.38(15) ?
C35 C30 C1 . . 118.73(14) ?
C32 C31 C30 . . 122.51(15) ?
C32 C31 H31 . . 118.7 ?
C30 C31 H31 . . 118.7 ?
C31 C32 C33 . . 118.69(15) ?
C31 C32 C36 . . 120.95(15) ?
C33 C32 C36 . . 120.35(15) ?
C34 C33 C32 . . 120.75(15) ?
C34 C33 H33 . . 119.6 ?
C32 C33 H33 . . 119.6 ?
C33 C34 C35 . . 121.27(16) ?
C33 C34 H34 . . 119.4 ?
C35 C34 H34 . . 119.4 ?
N1 C35 C34 . . 119.60(15) ?
N1 C35 C30 . . 121.32(14) ?
C34 C35 C30 . . 119.06(14) ?
C37 C36 C32 . . 177.37(18) ?
C36 C37 C38 . . 177.17(18) ?
C39 C38 C42 . . 117.71(16) ?
C39 C38 C37 . . 122.52(16) ?
C42 C38 C37 . . 119.75(16) ?
N40A C39 C38 . . 120.27(18) ?
C40 C39 C38 . . 120.27(18) ?
C40 C39 H39 . . 119.9 ?
C38 C39 H39 . . 119.9 ?
C42 N40 C41 . . 117.01(19) ?
C39 C40 C41 . . 118.06(19) ?
C39 C40 H40 . . 121.0 ?
C41 C40 H40 . . 121.0 ?
C42 C40A C41 . . 117.01(19) ?
C42 C40A H40A . . 121.5 ?
C41 C40A H40A . . 121.5 ?
C39 N40A C41 . . 118.06(19) ?
C40A C41 N40A . . 124.10(19) ?
N40 C41 C40 . . 124.10(19) ?
N40 C41 H41 . . 117.9 ?
C40 C41 H41 . . 117.9 ?
C40A C42 C38 . . 122.84(19) ?
N40 C42 C38 . . 122.84(19) ?
N40 C42 H42 . . 118.6 ?
C38 C42 H42 . . 118.6 ?
O3A C43 C44 . . 118.4(4) ?
O3 C43 C44 . . 95.0(4) ?
O3 C43 D43A . . 112.7 ?
C44 C43 D43A . . 112.7 ?
O3 C43 D43B . . 112.7 ?
C44 C43 D43B . . 112.7 ?
D43A C43 D43B . . 110.2 ?
O3A C43 D43C . . 107.7 ?
C44 C43 D43C . . 107.7 ?
O3A C43 D43D . . 107.7 ?
C44 C43 D43D . . 107.7 ?
D43C C43 D43D . . 107.1 ?
C43 C44 C45 . . 103.4(2) ?
C43 C44 D44A . . 111.1 ?
C45 C44 D44A . . 111.1 ?
C43 C44 D44B . . 111.1 ?
C45 C44 D44B . . 111.1 ?
D44A C44 D44B . . 109.1 ?
C46 C45 C44 . . 108.5(3) ?
C44 C45 C46A . . 99.0(3) ?
C46 C45 D45A . . 110.0 ?
C44 C45 D45A . . 110.0 ?
C46 C45 D45B . . 110.0 ?
C44 C45 D45B . . 110.0 ?
D45A C45 D45B . . 108.4 ?
C44 C45 D45C . . 112.0 ?
C46A C45 D45C . . 112.0 ?
C44 C45 D45D . . 112.0 ?
C46A C45 D45D . . 112.0 ?
D45C C45 D45D . . 109.7 ?
C16 N1 C35 . . 119.90(13) ?
C16 N1 C17 . . 119.50(13) ?
C35 N1 C17 . . 120.29(13) ?
C29 N3 C28 . . 116.72(17) ?
C4 O2 C5 . . 119.94(13) ?
C46 O3 C43 . . 110.5(4) ?
C45 C46 O3 . . 102.6(4) ?
C45 C46 D46A . . 111.2 ?
O3 C46 D46A . . 111.2 ?
C45 C46 D46B . . 111.2 ?
O3 C46 D46B . . 111.2 ?
D46A C46 D46B . . 109.2 ?
C43 O3A C46A . . 97.9(5) ?
O3A C46A C45 . . 110.7(5) ?
O3A C46A D46C . . 109.5 ?
C45 C46A D46C . . 109.5 ?
O3A C46A D46D . . 109.5 ?
C45 C46A D46D . . 109.5 ?
D46C C46A D46D . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C30 C1 C2 C3 . . . . 18.3(3) ?
C11 C1 C2 C3 . . . . -162.82(15) ?
C30 C1 C2 C4 . . . . -153.86(15) ?
C11 C1 C2 C4 . . . . 25.1(2) ?
C1 C2 C4 O1 . . . . 32.4(2) ?
C3 C2 C4 O1 . . . . -140.65(17) ?
C1 C2 C4 O2 . . . . -150.37(14) ?
C3 C2 C4 O2 . . . . 36.59(18) ?
C10 C5 C6 C7 . . . . -1.9(2) ?
O2 C5 C6 C7 . . . . -176.43(15) ?
C5 C6 C7 C8 . . . . 0.7(2) ?
C6 C7 C8 C9 . . . . 1.0(3) ?
C7 C8 C9 C10 . . . . -1.5(3) ?
C6 C5 C10 C9 . . . . 1.4(3) ?
O2 C5 C10 C9 . . . . 176.23(14) ?
C8 C9 C10 C5 . . . . 0.3(2) ?
C2 C1 C11 C12 . . . . 22.9(2) ?
C30 C1 C11 C12 . . . . -158.06(14) ?
C2 C1 C11 C16 . . . . -158.10(15) ?
C30 C1 C11 C16 . . . . 20.9(2) ?
C16 C11 C12 C13 . . . . 7.5(2) ?
C1 C11 C12 C13 . . . . -173.49(15) ?
C11 C12 C13 C14 . . . . -4.1(2) ?
C11 C12 C13 C23 . . . . 175.01(15) ?
C12 C13 C14 C15 . . . . -1.1(2) ?
C23 C13 C14 C15 . . . . 179.75(16) ?
C13 C14 C15 C16 . . . . 2.8(3) ?
C12 C11 C16 N1 . . . . 174.52(14) ?
C1 C11 C16 N1 . . . . -4.5(2) ?
C12 C11 C16 C15 . . . . -5.7(2) ?
C1 C11 C16 C15 . . . . 175.29(14) ?
C14 C15 C16 N1 . . . . -179.45(15) ?
C14 C15 C16 C11 . . . . 0.8(2) ?
N1 C17 C18 C19 . . . . -174.89(14) ?
C17 C18 C19 C20 . . . . 175.69(14) ?
C18 C19 C20 C21 . . . . -175.95(16) ?
C19 C20 C21 C22 . . . . 175.44(17) ?
C29 C25 C26 C27 . . . . 1.4(3) ?
C24 C25 C26 C27 . . . . -177.84(17) ?
C25 C26 C27 C28 . . . . -0.3(3) ?
C26 C27 C28 N3 . . . . -1.1(3) ?
C26 C25 C29 N3 . . . . -1.4(3) ?
C24 C25 C29 N3 . . . . 177.86(17) ?
C2 C1 C30 C31 . . . . -16.7(2) ?
C11 C1 C30 C31 . . . . 164.35(14) ?
C2 C1 C30 C35 . . . . 157.93(15) ?
C11 C1 C30 C35 . . . . -21.0(2) ?
C35 C30 C31 C32 . . . . -2.0(2) ?
C1 C30 C31 C32 . . . . 172.63(15) ?
C30 C31 C32 C33 . . . . 0.6(2) ?
C30 C31 C32 C36 . . . . -178.13(15) ?
C31 C32 C33 C34 . . . . 0.6(2) ?
C36 C32 C33 C34 . . . . 179.37(15) ?
C32 C33 C34 C35 . . . . -0.3(2) ?
C33 C34 C35 N1 . . . . -179.17(15) ?
C33 C34 C35 C30 . . . . -1.1(2) ?
C31 C30 C35 N1 . . . . -179.75(14) ?
C1 C30 C35 N1 . . . . 5.3(2) ?
C31 C30 C35 C34 . . . . 2.2(2) ?
C1 C30 C35 C34 . . . . -172.68(14) ?
C42 C38 C39 N40A . . . . -0.1(3) ?
C37 C38 C39 N40A . . . . -178.34(17) ?
C42 C38 C39 C40 . . . . -0.1(3) ?
C37 C38 C39 C40 . . . . -178.34(17) ?
C38 C39 C40 C41 . . . . 0.4(3) ?
C38 C39 N40A C41 . . . . 0.4(3) ?
C42 C40A C41 N40A . . . . -0.6(3) ?
C42 N40 C41 C40 . . . . -0.6(3) ?
C39 N40A C41 C40A . . . . -0.1(3) ?
C39 C40 C41 N40 . . . . -0.1(3) ?
C41 C40A C42 C38 . . . . 0.9(3) ?
C41 N40 C42 C38 . . . . 0.9(3) ?
C39 C38 C42 C40A . . . . -0.6(3) ?
C37 C38 C42 C40A . . . . 177.71(19) ?
C39 C38 C42 N40 . . . . -0.6(3) ?
C37 C38 C42 N40 . . . . 177.71(19) ?
O3A C43 C44 C45 . . . . 15.6(5) ?
O3 C43 C44 C45 . . . . 36.9(4) ?
C43 C44 C45 C46 . . . . -21.2(6) ?
C43 C44 C45 C46A . . . . 5.9(4) ?
C11 C16 N1 C35 . . . . -12.7(2) ?
C15 C16 N1 C35 . . . . 167.49(15) ?
C11 C16 N1 C17 . . . . 173.61(14) ?
C15 C16 N1 C17 . . . . -6.2(2) ?
C34 C35 N1 C16 . . . . -169.65(14) ?
C30 C35 N1 C16 . . . . 12.3(2) ?
C34 C35 N1 C17 . . . . 3.9(2) ?
C30 C35 N1 C17 . . . . -174.06(14) ?
C18 C17 N1 C16 . . . . 87.05(17) ?
C18 C17 N1 C35 . . . . -86.57(17) ?
C25 C29 N3 C28 . . . . 0.1(3) ?
C27 C28 N3 C29 . . . . 1.1(3) ?
O1 C4 O2 C5 . . . . 0.0(2) ?
C2 C4 O2 C5 . . . . -177.27(13) ?
C10 C5 O2 C4 . . . . 133.11(16) ?
C6 C5 O2 C4 . . . . -52.1(2) ?
C44 C43 O3 C46 . . . . -45.3(5) ?
C44 C45 C46 O3 . . . . -6.4(6) ?
C43 O3 C46 C45 . . . . 33.7(6) ?
C44 C43 O3A C46A . . . . -30.4(5) ?
C43 O3A C46A C45 . . . . 32.3(5) ?
C44 C45 C46A O3A . . . . -24.9(5) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
