# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_dm15813
_database_code_depnum_ccdc_archive 'CCDC 1445977'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;
_audit_creation_date             2015-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C36 H34 N2 O2'
_chemical_formula_sum            'C36 H34 N2 O2'
_chemical_formula_weight         526.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'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, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.463(5)
_cell_length_b                   12.095(2)
_cell_length_c                   20.499(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.456(7)
_cell_angle_gamma                90
_cell_volume                     5781(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.328
_cell_measurement_theta_min      2.503
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0540 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.8399. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19894
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.747
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2557
_reflns_number_total             5384
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1492P)²+3.8797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2948
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C36
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C33 \\sim O2 \\sim C36: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(O2) \\sim Ueq, Uanis(C36) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C31(H31), C32(H32), C34(H34), C35(H35)
4.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.28449(14) 0.5276(2) 0.30835(14) 0.0933(10) Uani 1 1 d . . . . .
O2 O 0.5430(2) 0.9531(3) 0.6428(2) 0.1414(14) Uani 1 1 d D U . . .
N1 N 0.29185(14) 0.8749(3) 0.25633(14) 0.0670(9) Uani 1 1 d . . . . .
H1 H 0.2691 0.9283 0.2433 0.080 Uiso 1 1 calc R U . . .
N2 N 0.40085(17) 0.7728(3) 0.43764(15) 0.0861(11) Uani 1 1 d . . . . .
H2 H 0.3936 0.8200 0.4065 0.103 Uiso 1 1 calc R U . . .
C1 C 0.33594(17) 0.8382(3) 0.22459(16) 0.0668(11) Uani 1 1 d . . . . .
C2 C 0.3539(2) 0.8740(4) 0.16681(19) 0.0914(14) Uani 1 1 d . . . . .
H2A H 0.3359 0.9324 0.1433 0.110 Uiso 1 1 calc R U . . .
C3 C 0.3990(3) 0.8207(6) 0.1455(2) 0.122(2) Uani 1 1 d . . . . .
H3 H 0.4119 0.8420 0.1061 0.146 Uiso 1 1 calc R U . . .
C4 C 0.4262(3) 0.7358(6) 0.1808(3) 0.129(2) Uani 1 1 d . . . . .
H4 H 0.4570 0.7008 0.1647 0.154 Uiso 1 1 calc R U . . .
C5 C 0.4092(2) 0.7012(4) 0.2390(2) 0.0964(15) Uani 1 1 d . . . . .
H5 H 0.4287 0.6447 0.2628 0.116 Uiso 1 1 calc R U . . .
C6 C 0.36246(17) 0.7520(3) 0.26182(16) 0.0655(10) Uani 1 1 d . . . . .
C7 C 0.33243(16) 0.7380(3) 0.31793(15) 0.0593(9) Uani 1 1 d . . . . .
C8 C 0.28909(16) 0.8140(3) 0.31226(16) 0.0600(10) Uani 1 1 d . . . . .
C9 C 0.24344(17) 0.8346(3) 0.35587(17) 0.0682(11) Uani 1 1 d . . . . .
H9 H 0.2469 0.7753 0.3887 0.082 Uiso 1 1 calc R U . . .
C10 C 0.25571(18) 0.9412(4) 0.3933(2) 0.0790(12) Uani 1 1 d . . . . .
C11 C 0.2476(2) 1.0440(4) 0.3632(3) 0.0976(15) Uani 1 1 d . . . . .
H11 H 0.2318 1.0478 0.3196 0.117 Uiso 1 1 calc R U . . .
C12 C 0.2623(3) 1.1398(5) 0.3967(4) 0.133(2) Uani 1 1 d . . . . .
H12 H 0.2560 1.2078 0.3759 0.159 Uiso 1 1 calc R U . . .
C13 C 0.2858(3) 1.1356(9) 0.4594(5) 0.164(4) Uani 1 1 d . . . . .
H13 H 0.2970 1.2009 0.4811 0.196 Uiso 1 1 calc R U . . .
C14 C 0.2936(3) 1.0364(10) 0.4924(4) 0.164(4) Uani 1 1 d . . . . .
H14 H 0.3087 1.0344 0.5363 0.197 Uiso 1 1 calc R U . . .
C15 C 0.2781(2) 0.9374(6) 0.4574(2) 0.120(2) Uani 1 1 d . . . . .
H15 H 0.2832 0.8696 0.4786 0.144 Uiso 1 1 calc R U . . .
C16 C 0.18407(18) 0.8229(4) 0.3182(2) 0.0758(11) Uani 1 1 d . . . . .
C17 C 0.1745(2) 0.7378(5) 0.2736(3) 0.1148(18) Uani 1 1 d . . . . .
H17 H 0.2039 0.6883 0.2684 0.138 Uiso 1 1 calc R U . . .
C18 C 0.1233(3) 0.7246(7) 0.2374(4) 0.145(3) Uani 1 1 d . . . . .
H18 H 0.1187 0.6676 0.2068 0.174 Uiso 1 1 calc R U . . .
C19 C 0.0797(3) 0.7906(7) 0.2443(4) 0.133(2) Uani 1 1 d . . . . .
H19 H 0.0446 0.7793 0.2194 0.159 Uiso 1 1 calc R U . . .
C20 C 0.0864(2) 0.8751(6) 0.2881(4) 0.1183(19) Uani 1 1 d . . . . .
H20 H 0.0558 0.9222 0.2929 0.142 Uiso 1 1 calc R U . . .
C21 C 0.1392(2) 0.8915(5) 0.3260(2) 0.0958(14) Uani 1 1 d . . . . .
H21 H 0.1436 0.9489 0.3563 0.115 Uiso 1 1 calc R U . . .
C22 C 0.34299(16) 0.6527(3) 0.36934(16) 0.0617(10) Uani 1 1 d . . . . .
C23 C 0.37698(17) 0.6727(3) 0.42665(16) 0.0636(10) Uani 1 1 d . . . . .
C24 C 0.38881(19) 0.5879(3) 0.47860(18) 0.0753(12) Uani 1 1 d . . . . .
H24A H 0.3601 0.5934 0.5090 0.090 Uiso 1 1 calc R U . . .
H24B H 0.4259 0.6028 0.5029 0.090 Uiso 1 1 calc R U . . .
C25 C 0.3886(2) 0.4712(3) 0.4513(2) 0.0794(12) Uani 1 1 d . . . . .
C26 C 0.3334(2) 0.4552(4) 0.4061(2) 0.0890(14) Uani 1 1 d . . . . .
H26A H 0.3361 0.3864 0.3823 0.107 Uiso 1 1 calc R U . . .
H26B H 0.3021 0.4474 0.4329 0.107 Uiso 1 1 calc R U . . .
C27 C 0.31843(18) 0.5459(3) 0.35703(18) 0.0696(11) Uani 1 1 d . . . . .
C28 C 0.3920(3) 0.3891(4) 0.5083(3) 0.118(2) Uani 1 1 d . . . . .
H28A H 0.4268 0.4008 0.5367 0.177 Uiso 1 1 calc R U . . .
H28B H 0.3914 0.3150 0.4915 0.177 Uiso 1 1 calc R U . . .
H28C H 0.3597 0.3998 0.5326 0.177 Uiso 1 1 calc R U . . .
C29 C 0.4394(2) 0.4555(4) 0.4136(2) 0.1035(16) Uani 1 1 d . . . . .
H29A H 0.4357 0.5030 0.3758 0.155 Uiso 1 1 calc R U . . .
H29B H 0.4411 0.3799 0.3997 0.155 Uiso 1 1 calc R U . . .
H29C H 0.4739 0.4737 0.4412 0.155 Uiso 1 1 calc R U . . .
C30 C 0.4364(2) 0.8116(3) 0.49359(18) 0.0719(12) Uani 1 1 d . . . . .
C31 C 0.4164(2) 0.8295(5) 0.5522(2) 0.0994(16) Uani 1 1 d . . . . .
H31 H 0.3790 0.8102 0.5580 0.119 Uiso 1 1 calc R U . . .
C32 C 0.4514(3) 0.8762(5) 0.6032(2) 0.1145(19) Uani 1 1 d . . . . .
H32 H 0.4370 0.8893 0.6430 0.137 Uiso 1 1 calc R U . . .
C33 C 0.5057(3) 0.9030(4) 0.5963(3) 0.1035(16) Uani 1 1 d . U . . .
C34 C 0.5265(2) 0.8816(5) 0.5389(3) 0.1066(17) Uani 1 1 d . . . . .
H34 H 0.5647 0.8968 0.5343 0.128 Uiso 1 1 calc R U . . .
C35 C 0.4918(2) 0.8377(4) 0.4874(2) 0.0944(15) Uani 1 1 d . . . . .
H35 H 0.5063 0.8255 0.4476 0.113 Uiso 1 1 calc R U . . .
C36 C 0.5303(4) 1.0043(9) 0.6909(4) 0.210(3) Uani 1 1 d D U . . .
H36A H 0.5294 1.0821 0.6815 0.315 Uiso 1 1 calc R U . . .
H36B H 0.5583 0.9898 0.7278 0.315 Uiso 1 1 calc R U . . .
H36C H 0.4931 0.9809 0.7010 0.315 Uiso 1 1 calc DR U . . .


_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 C27 1.225(4) . ?
O2 C33 1.361(6) . ?
O2 C36 1.230(8) . ?
N1 H1 0.8600 . ?
N1 C1 1.357(5) . ?
N1 C8 1.371(4) . ?
N2 H2 0.8600 . ?
N2 C23 1.343(5) . ?
N2 C30 1.420(5) . ?
C1 C2 1.371(6) . ?
C1 C6 1.396(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.354(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(6) . ?
C6 C7 1.425(5) . ?
C7 C8 1.367(5) . ?
C7 C22 1.475(5) . ?
C8 C9 1.491(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.512(6) . ?
C9 C16 1.521(5) . ?
C10 C11 1.391(7) . ?
C10 C15 1.360(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.342(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.421(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(7) . ?
C16 C21 1.364(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.348(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.318(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.401(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(4) . ?
C22 C27 1.425(5) . ?
C23 C24 1.481(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.519(6) . ?
C25 C26 1.520(6) . ?
C25 C28 1.530(6) . ?
C25 C29 1.503(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.503(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.356(6) . ?
C30 C35 1.355(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.375(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.338(8) . ?
C33 C34 1.349(8) . ?
C34 H34 0.9300 . ?
C34 C35 1.366(6) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C36 O2 C33 126.2(7) . . ?
C1 N1 H1 125.2 . . ?
C1 N1 C8 109.6(3) . . ?
C8 N1 H1 125.2 . . ?
C23 N2 H2 115.5 . . ?
C23 N2 C30 129.0(3) . . ?
C30 N2 H2 115.5 . . ?
N1 C1 C2 129.5(4) . . ?
N1 C1 C6 107.4(3) . . ?
C2 C1 C6 123.1(4) . . ?
C1 C2 H2A 121.4 . . ?
C3 C2 C1 117.1(5) . . ?
C3 C2 H2A 121.4 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(5) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 107.5(3) . . ?
C5 C6 C1 117.9(4) . . ?
C5 C6 C7 134.6(4) . . ?
C6 C7 C22 127.0(3) . . ?
C8 C7 C6 106.4(3) . . ?
C8 C7 C22 126.5(3) . . ?
N1 C8 C9 121.1(3) . . ?
C7 C8 N1 109.2(3) . . ?
C7 C8 C9 129.7(3) . . ?
C8 C9 H9 106.3 . . ?
C8 C9 C10 109.8(3) . . ?
C8 C9 C16 111.0(3) . . ?
C10 C9 H9 106.3 . . ?
C10 C9 C16 116.6(4) . . ?
C16 C9 H9 106.3 . . ?
C11 C10 C9 121.9(4) . . ?
C15 C10 C9 119.5(5) . . ?
C15 C10 C11 118.5(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.3(6) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(8) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(8) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.3(7) . . ?
C15 C14 H14 120.9 . . ?
C10 C15 C14 120.5(7) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C9 118.6(4) . . ?
C21 C16 C9 124.0(4) . . ?
C21 C16 C17 117.4(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(6) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.5(7) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(6) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(6) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.7(5) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C7 121.7(3) . . ?
C23 C22 C27 119.9(3) . . ?
C27 C22 C7 118.3(3) . . ?
N2 C23 C22 119.8(3) . . ?
N2 C23 C24 117.5(3) . . ?
C22 C23 C24 122.7(4) . . ?
C23 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C23 C24 C25 112.7(3) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C24 C25 C26 108.1(4) . . ?
C24 C25 C28 108.9(4) . . ?
C26 C25 C28 110.5(4) . . ?
C29 C25 C24 109.7(4) . . ?
C29 C25 C26 110.0(4) . . ?
C29 C25 C28 109.7(4) . . ?
C25 C26 H26A 108.4 . . ?
C25 C26 H26B 108.4 . . ?
H26A C26 H26B 107.4 . . ?
C27 C26 C25 115.7(4) . . ?
C27 C26 H26A 108.4 . . ?
C27 C26 H26B 108.4 . . ?
O1 C27 C22 121.4(4) . . ?
O1 C27 C26 119.6(4) . . ?
C22 C27 C26 119.0(3) . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 N2 122.5(4) . . ?
C35 C30 N2 118.9(4) . . ?
C35 C30 C31 118.5(4) . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.2(5) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 119.6 . . ?
C33 C32 C31 120.9(5) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 O2 125.4(6) . . ?
C32 C33 C34 119.2(4) . . ?
C34 C33 O2 115.4(6) . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.4(5) . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 120.8(5) . . ?
C30 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
O2 C36 H36A 109.5 . . ?
O2 C36 H36B 109.5 . . ?
O2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C33 C34 C35 -176.0(5) . . . . ?
N1 C1 C2 C3 -178.8(5) . . . . ?
N1 C1 C6 C5 -179.8(4) . . . . ?
N1 C1 C6 C7 -0.1(4) . . . . ?
N1 C8 C9 C10 -73.2(4) . . . . ?
N1 C8 C9 C16 57.2(5) . . . . ?
N2 C23 C24 C25 -149.6(4) . . . . ?
N2 C30 C31 C32 -174.3(4) . . . . ?
N2 C30 C35 C34 176.0(4) . . . . ?
C1 N1 C8 C7 1.1(4) . . . . ?
C1 N1 C8 C9 -178.3(3) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C1 C6 C7 C8 0.7(4) . . . . ?
C1 C6 C7 C22 176.4(3) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C2 C1 C6 C7 -179.9(4) . . . . ?
C2 C3 C4 C5 -0.2(10) . . . . ?
C3 C4 C5 C6 1.6(9) . . . . ?
C4 C5 C6 C1 -1.6(7) . . . . ?
C4 C5 C6 C7 178.8(5) . . . . ?
C5 C6 C7 C8 -179.6(5) . . . . ?
C5 C6 C7 C22 -3.9(7) . . . . ?
C6 C1 C2 C3 1.0(7) . . . . ?
C6 C7 C8 N1 -1.1(4) . . . . ?
C6 C7 C8 C9 178.2(3) . . . . ?
C6 C7 C22 C23 95.3(5) . . . . ?
C6 C7 C22 C27 -82.4(5) . . . . ?
C7 C8 C9 C10 107.5(4) . . . . ?
C7 C8 C9 C16 -122.1(4) . . . . ?
C7 C22 C23 N2 1.2(6) . . . . ?
C7 C22 C23 C24 -179.2(4) . . . . ?
C7 C22 C27 O1 -7.6(6) . . . . ?
C7 C22 C27 C26 174.2(4) . . . . ?
C8 N1 C1 C2 179.2(4) . . . . ?
C8 N1 C1 C6 -0.6(4) . . . . ?
C8 C7 C22 C23 -89.9(5) . . . . ?
C8 C7 C22 C27 92.4(5) . . . . ?
C8 C9 C10 C11 73.8(5) . . . . ?
C8 C9 C10 C15 -102.9(5) . . . . ?
C8 C9 C16 C17 41.0(6) . . . . ?
C8 C9 C16 C21 -139.3(4) . . . . ?
C9 C10 C11 C12 -175.8(5) . . . . ?
C9 C10 C15 C14 175.7(5) . . . . ?
C9 C16 C17 C18 -178.2(6) . . . . ?
C9 C16 C21 C20 178.9(4) . . . . ?
C10 C9 C16 C17 167.7(4) . . . . ?
C10 C9 C16 C21 -12.6(6) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C11 C10 C15 C14 -1.1(8) . . . . ?
C11 C12 C13 C14 -2.5(12) . . . . ?
C12 C13 C14 C15 2.3(13) . . . . ?
C13 C14 C15 C10 -0.4(11) . . . . ?
C15 C10 C11 C12 0.9(8) . . . . ?
C16 C9 C10 C11 -53.5(6) . . . . ?
C16 C9 C10 C15 129.8(5) . . . . ?
C16 C17 C18 C19 -2.0(11) . . . . ?
C17 C16 C21 C20 -1.5(7) . . . . ?
C17 C18 C19 C20 1.1(12) . . . . ?
C18 C19 C20 C21 -0.5(10) . . . . ?
C19 C20 C21 C16 0.7(9) . . . . ?
C21 C16 C17 C18 2.1(9) . . . . ?
C22 C7 C8 N1 -176.8(3) . . . . ?
C22 C7 C8 C9 2.5(6) . . . . ?
C22 C23 C24 C25 30.8(6) . . . . ?
C23 N2 C30 C31 -69.9(6) . . . . ?
C23 N2 C30 C35 113.9(5) . . . . ?
C23 C22 C27 O1 174.7(4) . . . . ?
C23 C22 C27 C26 -3.5(6) . . . . ?
C23 C24 C25 C26 -51.3(5) . . . . ?
C23 C24 C25 C28 -171.4(4) . . . . ?
C23 C24 C25 C29 68.6(5) . . . . ?
C24 C25 C26 C27 47.7(5) . . . . ?
C25 C26 C27 O1 160.4(4) . . . . ?
C25 C26 C27 C22 -21.4(6) . . . . ?
C27 C22 C23 N2 178.9(4) . . . . ?
C27 C22 C23 C24 -1.5(6) . . . . ?
C28 C25 C26 C27 166.8(4) . . . . ?
C29 C25 C26 C27 -72.0(5) . . . . ?
C30 N2 C23 C22 178.9(4) . . . . ?
C30 N2 C23 C24 -0.7(7) . . . . ?
C30 C31 C32 C33 -1.1(9) . . . . ?
C31 C30 C35 C34 -0.4(7) . . . . ?
C31 C32 C33 O2 177.5(5) . . . . ?
C31 C32 C33 C34 -1.4(9) . . . . ?
C32 C33 C34 C35 3.0(8) . . . . ?
C33 C34 C35 C30 -2.1(8) . . . . ?
C35 C30 C31 C32 2.0(8) . . . . ?
C36 O2 C33 C32 -18.2(10) . . . . ?
C36 O2 C33 C34 160.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dm15793_0m
_database_code_depnum_ccdc_archive 'CCDC 1445978'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H30 N O3'
_chemical_formula_weight         500.59

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      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                   9.861(5)
_cell_length_b                   10.455(5)
_cell_length_c                   15.398(8)
_cell_angle_alpha                89.660(9)
_cell_angle_beta                 76.844(9)
_cell_angle_gamma                63.337(8)
_cell_volume                     1373.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      4.386
_cell_measurement_theta_max      42.996

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             530
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9088
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4857
_reflns_number_gt                2392
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1474P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4857
_refine_ls_number_parameters     349
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2548
_refine_ls_wR_factor_gt          0.2057
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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 0.3091(4) 0.2884(3) 0.2844(2) 0.0530(8) Uani 1 1 d . . . . .
O1 O 0.2925(4) 1.0246(3) 0.3315(2) 0.0968(11) Uani 1 1 d . . . . .
O2 O 0.2303(3) 0.8558(3) 0.37570(18) 0.0627(8) Uani 1 1 d . . . . .
O3 O 0.1460(3) 0.6988(3) 0.43124(18) 0.0723(9) Uani 1 1 d . . . . .
C1 C 0.2105(4) 0.4834(4) 0.2132(2) 0.0471(9) Uani 1 1 d . . . . .
C2 C 0.1251(5) 0.5664(4) 0.1550(2) 0.0586(10) Uani 1 1 d . . . . .
H2 H 0.1148 0.6584 0.1475 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0568(5) 0.5109(5) 0.1093(3) 0.0686(12) Uani 1 1 d . . . . .
H3 H -0.0002 0.5660 0.0705 0.082 Uiso 1 1 calc R U . . .
C4 C 0.0705(5) 0.3741(5) 0.1194(3) 0.0730(13) Uani 1 1 d . . . . .
H4 H 0.0223 0.3396 0.0872 0.088 Uiso 1 1 calc R U . . .
C5 C 0.1529(5) 0.2889(5) 0.1755(3) 0.0668(12) Uani 1 1 d . . . . .
H5 H 0.1622 0.1971 0.1822 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2231(4) 0.3460(4) 0.2225(2) 0.0506(9) Uani 1 1 d . . . . .
C7 C 0.3495(4) 0.3865(4) 0.3132(2) 0.0476(9) Uani 1 1 d . . . . .
C8 C 0.2921(4) 0.5062(4) 0.2723(2) 0.0445(8) Uani 1 1 d . . . . .
C9 C 0.3047(4) 0.6405(4) 0.2847(2) 0.0454(8) Uani 1 1 d . . . . .
C10 C 0.2299(4) 0.7279(4) 0.3613(3) 0.0493(9) Uani 1 1 d . . . . .
C11 C 0.3085(5) 0.9064(5) 0.3122(3) 0.0686(12) Uani 1 1 d . . . . .
C12 C 0.3993(5) 0.8134(4) 0.2285(3) 0.0622(11) Uani 1 1 d . . . . .
C13 C 0.3959(4) 0.6828(4) 0.2159(3) 0.0545(10) Uani 1 1 d . . . . .
C14 C 0.4878(5) 0.5952(5) 0.1355(3) 0.0747(13) Uani 1 1 d . . . . .
H14 H 0.4867 0.5085 0.1238 0.090 Uiso 1 1 calc R U . . .
C15 C 0.5792(7) 0.6376(7) 0.0742(4) 0.1047(18) Uani 1 1 d . . . . .
H15 H 0.6420 0.5776 0.0215 0.126 Uiso 1 1 calc R U . . .
C16 C 0.5806(7) 0.7671(7) 0.0885(4) 0.116(2) Uani 1 1 d . . . . .
H16 H 0.6429 0.7938 0.0452 0.139 Uiso 1 1 calc R U . . .
C17 C 0.4919(7) 0.8553(6) 0.1651(4) 0.0988(17) Uani 1 1 d . . . . .
H17 H 0.4928 0.9425 0.1752 0.119 Uiso 1 1 calc R U . . .
C18 C 0.0674(7) 0.7922(6) 0.5118(3) 0.0984(17) Uani 1 1 d . . . . .
H18A H 0.1296 0.8361 0.5234 0.148 Uiso 1 1 calc R U . . .
H18B H 0.0515 0.7384 0.5604 0.148 Uiso 1 1 calc R U . . .
H18C H -0.0322 0.8656 0.5063 0.148 Uiso 1 1 calc R U . . .
C19 C 0.4468(4) 0.3536(4) 0.3810(2) 0.0493(9) Uani 1 1 d . . . . .
H19 H 0.4875 0.4240 0.3768 0.059 Uiso 1 1 calc R U . . .
C20 C 0.3552(4) 0.3739(4) 0.4777(2) 0.0482(9) Uani 1 1 d . . . . .
C21 C 0.4235(5) 0.3810(4) 0.5448(3) 0.0587(10) Uani 1 1 d . . . . .
H21 H 0.5256 0.3692 0.5298 0.070 Uiso 1 1 calc R U . . .
C22 C 0.3447(5) 0.4049(5) 0.6332(3) 0.0663(11) Uani 1 1 d . . . . .
H22 H 0.3935 0.4095 0.6773 0.080 Uiso 1 1 calc R U . . .
C23 C 0.1939(5) 0.4223(4) 0.6574(3) 0.0661(11) Uani 1 1 d . . . . .
H23 H 0.1397 0.4397 0.7175 0.079 Uiso 1 1 calc R U . . .
C24 C 0.1251(5) 0.4137(5) 0.5916(3) 0.0669(12) Uani 1 1 d . . . . .
H24 H 0.0235 0.4243 0.6069 0.080 Uiso 1 1 calc R U . . .
C25 C 0.2051(4) 0.3895(4) 0.5026(3) 0.0552(10) Uani 1 1 d . . . . .
H25 H 0.1567 0.3837 0.4586 0.066 Uiso 1 1 calc R U . . .
C26 C 0.5889(4) 0.2077(4) 0.3574(3) 0.0572(10) Uani 1 1 d . . . . .
C27 C 0.5808(6) 0.0858(5) 0.3843(4) 0.0884(15) Uani 1 1 d . . . . .
H27 H 0.4861 0.0936 0.4186 0.106 Uiso 1 1 calc R U . . .
C28 C 0.7084(9) -0.0474(6) 0.3622(5) 0.123(2) Uani 1 1 d . . . . .
H28 H 0.6992 -0.1284 0.3812 0.148 Uiso 1 1 calc R U . . .
C29 C 0.8464(10) -0.0618(8) 0.3132(5) 0.134(3) Uani 1 1 d . . . . .
H29 H 0.9324 -0.1526 0.2976 0.161 Uiso 1 1 calc R U . . .
C30 C 0.8608(7) 0.0581(9) 0.2860(4) 0.123(2) Uani 1 1 d . . . . .
H30 H 0.9570 0.0493 0.2535 0.148 Uiso 1 1 calc R U . . .
C31 C 0.7293(6) 0.1936(6) 0.3079(3) 0.0901(15) Uani 1 1 d . . . . .
H31 H 0.7378 0.2747 0.2884 0.108 Uiso 1 1 calc R U . . .
C32 C 0.3395(16) 0.8779(16) 0.9193(8) 0.230(5) Uani 1 1 d D . . . .
H32A H 0.3188 0.9338 0.8698 0.346 Uiso 1 1 calc R U . . .
H32B H 0.4256 0.7841 0.8975 0.346 Uiso 1 1 calc R U . . .
H32C H 0.3657 0.9252 0.9612 0.346 Uiso 1 1 calc R U . . .
C33 C 0.194(2) 0.863(2) 0.9661(12) 0.333(11) Uani 1 1 d D . . . .
H33A H 0.2066 0.8171 1.0206 0.399 Uiso 1 1 calc R U . . .
H33B H 0.1698 0.8077 0.9268 0.399 Uiso 1 1 calc R U . . .
C34 C 0.064(3) 1.022(2) 0.9870(17) 0.415(19) Uani 1 1 d D . . . .
H34A H 0.0707 1.0748 1.0362 0.498 Uiso 1 1 calc R U . . .
H34B H 0.0576 1.0751 0.9348 0.498 Uiso 1 1 calc R U . . .
H1 H 0.316(4) 0.196(4) 0.304(2) 0.051(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.364(4) . ?
N1 C6 1.376(4) . ?
N1 H1 0.99(4) . ?
O1 C11 1.204(5) . ?
O2 C10 1.359(4) . ?
O2 C11 1.359(5) . ?
O3 C10 1.325(4) . ?
O3 C18 1.411(5) . ?
C1 C6 1.395(5) . ?
C1 C2 1.395(5) . ?
C1 C8 1.428(5) . ?
C2 C3 1.362(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.340(5) . ?
C7 C19 1.512(5) . ?
C8 C9 1.481(5) . ?
C9 C10 1.335(5) . ?
C9 C13 1.430(5) . ?
C11 C12 1.455(6) . ?
C12 C17 1.388(6) . ?
C12 C13 1.397(5) . ?
C13 C14 1.397(6) . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C26 1.509(5) . ?
C19 C20 1.516(5) . ?
C19 H19 0.9800 . ?
C20 C21 1.375(5) . ?
C20 C25 1.375(5) . ?
C21 C22 1.366(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.363(6) . ?
C26 C27 1.368(6) . ?
C27 C28 1.370(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.339(10) . ?
C28 H28 0.9300 . ?
C29 C30 1.376(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.400(8) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.531(13) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.559(18) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C34 1.50(4) 2_577 ?
C34 H34A 0.9700 . ?
C34 H34B 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
C7 N1 C6 108.7(3) . . ?
C7 N1 H1 133.9(19) . . ?
C6 N1 H1 116.8(19) . . ?
C10 O2 C11 122.3(3) . . ?
C10 O3 C18 122.5(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C8 106.7(3) . . ?
C2 C1 C8 134.6(3) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 116.9(4) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
N1 C6 C1 107.3(3) . . ?
N1 C6 C5 130.4(4) . . ?
C1 C6 C5 122.3(4) . . ?
C8 C7 N1 110.1(3) . . ?
C8 C7 C19 128.7(3) . . ?
N1 C7 C19 121.2(3) . . ?
C7 C8 C1 107.1(3) . . ?
C7 C8 C9 128.4(3) . . ?
C1 C8 C9 124.4(3) . . ?
C10 C9 C13 117.1(3) . . ?
C10 C9 C8 120.9(3) . . ?
C13 C9 C8 122.0(3) . . ?
O3 C10 C9 123.0(3) . . ?
O3 C10 O2 112.9(3) . . ?
C9 C10 O2 124.0(3) . . ?
O1 C11 O2 115.8(4) . . ?
O1 C11 C12 127.5(4) . . ?
O2 C11 C12 116.7(3) . . ?
C17 C12 C13 122.2(4) . . ?
C17 C12 C11 118.5(4) . . ?
C13 C12 C11 119.3(3) . . ?
C12 C13 C14 117.5(4) . . ?
C12 C13 C9 120.4(4) . . ?
C14 C13 C9 122.1(4) . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.7(5) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 118.8(5) . . ?
C16 C17 H17 120.6 . . ?
C12 C17 H17 120.6 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C19 C7 112.2(3) . . ?
C26 C19 C20 111.6(3) . . ?
C7 C19 C20 114.6(3) . . ?
C26 C19 H19 105.9 . . ?
C7 C19 H19 105.9 . . ?
C20 C19 H19 105.9 . . ?
C21 C20 C25 117.6(4) . . ?
C21 C20 C19 118.6(3) . . ?
C25 C20 C19 123.7(3) . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 120.5(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 118.7(4) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.5(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 121.2(3) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C31 C26 C27 118.0(4) . . ?
C31 C26 C19 120.7(4) . . ?
C27 C26 C19 121.3(4) . . ?
C26 C27 C28 121.8(6) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C29 C28 C27 120.4(7) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.8(7) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C31 119.4(6) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C26 C31 C30 120.6(6) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C33 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C32 C33 C34 102.5(15) . . ?
C32 C33 H33A 111.3 . . ?
C34 C33 H33A 111.3 . . ?
C32 C33 H33B 111.3 . . ?
C34 C33 H33B 111.3 . . ?
H33A C33 H33B 109.2 . . ?
C34 C34 C33 91.9(18) 2_577 . ?
C34 C34 H34A 113.3 2_577 . ?
C33 C34 H34A 113.3 . . ?
C34 C34 H34B 113.3 2_577 . ?
C33 C34 H34B 113.3 . . ?
H34A C34 H34B 110.6 . . ?

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 0.0(5) . . . . ?
C8 C1 C2 C3 -178.0(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C7 N1 C6 C1 0.0(4) . . . . ?
C7 N1 C6 C5 -178.6(4) . . . . ?
C2 C1 C6 N1 -178.7(3) . . . . ?
C8 C1 C6 N1 -0.2(4) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C8 C1 C6 C5 178.5(3) . . . . ?
C4 C5 C6 N1 178.3(4) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C6 N1 C7 C8 0.3(4) . . . . ?
C6 N1 C7 C19 -179.2(3) . . . . ?
N1 C7 C8 C1 -0.4(4) . . . . ?
C19 C7 C8 C1 179.0(3) . . . . ?
N1 C7 C8 C9 178.6(3) . . . . ?
C19 C7 C8 C9 -2.0(6) . . . . ?
C6 C1 C8 C7 0.3(4) . . . . ?
C2 C1 C8 C7 178.5(4) . . . . ?
C6 C1 C8 C9 -178.7(3) . . . . ?
C2 C1 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C10 -68.6(5) . . . . ?
C1 C8 C9 C10 110.2(4) . . . . ?
C7 C8 C9 C13 111.6(4) . . . . ?
C1 C8 C9 C13 -69.6(5) . . . . ?
C18 O3 C10 C9 -180.0(4) . . . . ?
C18 O3 C10 O2 -0.5(6) . . . . ?
C13 C9 C10 O3 -177.7(3) . . . . ?
C8 C9 C10 O3 2.6(5) . . . . ?
C13 C9 C10 O2 2.9(5) . . . . ?
C8 C9 C10 O2 -176.8(3) . . . . ?
C11 O2 C10 O3 -179.5(3) . . . . ?
C11 O2 C10 C9 -0.1(5) . . . . ?
C10 O2 C11 O1 176.0(4) . . . . ?
C10 O2 C11 C12 -3.0(5) . . . . ?
O1 C11 C12 C17 6.8(7) . . . . ?
O2 C11 C12 C17 -174.4(4) . . . . ?
O1 C11 C12 C13 -175.8(4) . . . . ?
O2 C11 C12 C13 3.0(6) . . . . ?
C17 C12 C13 C14 -1.2(6) . . . . ?
C11 C12 C13 C14 -178.5(4) . . . . ?
C17 C12 C13 C9 177.0(4) . . . . ?
C11 C12 C13 C9 -0.3(6) . . . . ?
C10 C9 C13 C12 -2.7(5) . . . . ?
C8 C9 C13 C12 177.1(3) . . . . ?
C10 C9 C13 C14 175.5(4) . . . . ?
C8 C9 C13 C14 -4.8(6) . . . . ?
C12 C13 C14 C15 1.7(6) . . . . ?
C9 C13 C14 C15 -176.4(4) . . . . ?
C13 C14 C15 C16 -1.6(9) . . . . ?
C14 C15 C16 C17 0.9(10) . . . . ?
C15 C16 C17 C12 -0.3(10) . . . . ?
C13 C12 C17 C16 0.5(8) . . . . ?
C11 C12 C17 C16 177.8(5) . . . . ?
C8 C7 C19 C26 -131.6(4) . . . . ?
N1 C7 C19 C26 47.7(5) . . . . ?
C8 C7 C19 C20 99.7(4) . . . . ?
N1 C7 C19 C20 -80.9(4) . . . . ?
C26 C19 C20 C21 66.7(4) . . . . ?
C7 C19 C20 C21 -164.4(3) . . . . ?
C26 C19 C20 C25 -115.1(4) . . . . ?
C7 C19 C20 C25 13.8(5) . . . . ?
C25 C20 C21 C22 -1.0(6) . . . . ?
C19 C20 C21 C22 177.3(4) . . . . ?
C20 C21 C22 C23 0.2(6) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C21 C20 C25 C24 1.0(6) . . . . ?
C19 C20 C25 C24 -177.2(3) . . . . ?
C23 C24 C25 C20 -0.2(6) . . . . ?
C7 C19 C26 C31 92.5(4) . . . . ?
C20 C19 C26 C31 -137.3(4) . . . . ?
C7 C19 C26 C27 -87.1(5) . . . . ?
C20 C19 C26 C27 43.1(5) . . . . ?
C31 C26 C27 C28 -0.6(7) . . . . ?
C19 C26 C27 C28 179.1(5) . . . . ?
C26 C27 C28 C29 0.3(10) . . . . ?
C27 C28 C29 C30 0.9(11) . . . . ?
C28 C29 C30 C31 -1.8(11) . . . . ?
C27 C26 C31 C30 -0.4(7) . . . . ?
C19 C26 C31 C30 180.0(4) . . . . ?
C29 C30 C31 C26 1.6(9) . . . . ?
C32 C33 C34 C34 169.4(19) . . . 2_577 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545
N1 H1 O1 0.99(4) 1.94(4) 2.913(4) 168(3) 1_545

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

