# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1532914'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        3b_le-4-140
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H40 N4 O'
_chemical_formula_sum            'C33 H40 N4 O'
_chemical_formula_weight         508.69

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.6312(2)
_cell_length_b                   15.7365(3)
_cell_length_c                   18.2828(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3058.67(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    140.00(10)
_cell_measurement_reflns_used    8005
_cell_measurement_theta_min      4.8030
_cell_measurement_theta_max      75.5010

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 11 0.1149
-2 -2 -11 0.0100
-1 -9 -5 0.0555
1 -8 8 0.1161
0 10 -2 0.0687
5 6 6 0.1035
4 -5 8 0.0970
-7 -1 -1 0.0968
7 1 1 0.0200
-5 -3 7 0.1100
-5 4 6 0.1068

_diffrn_ambient_temperature      140.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -18.00   1.00    8.23    --  -40.91 -38.00  90.00   92
  2  ω    -68.00  26.00   1.00    8.23    --  -40.91  57.00   0.00   94
  3  ω    -42.00 -11.00   1.00    8.23    --  -40.91 125.00   0.00   31
  4  ω   -111.00 -21.00   1.00    8.23    --  -40.91 -57.00-150.00   90
  5  ω     10.00  39.00   1.00    8.23    --   40.91  77.00-150.00   29
  6  ω     40.00  97.00   1.00    8.23    --   40.91-125.00  90.00   57
  7  ω     90.00 116.00   1.00    8.23    --   40.91  77.00-150.00   26
  8  ω     32.00 165.00   1.00   32.95    --  111.85 -15.00   0.00  133
  9  ω     37.00 139.00   1.00   32.95    --  111.85 -30.00-180.00  102
 10  ω     89.00 178.00   1.00   32.95    --  111.85  45.00   0.00   89
 11  ω     57.00 141.00   1.00   32.95    --  111.85 -61.00  60.00   84
 12  ω     41.00 118.00   1.00   32.95    --  111.85-125.00  60.00   77
 13  ω     33.00 103.00   1.00   32.95    --  111.85 -94.00  90.00   70
 14  ω    108.00 134.00   1.00   32.95    --  111.85 125.00 150.00   26
 15  ω    152.00 178.00   1.00   32.95    --  111.85 125.00 150.00   26
 16  ω     55.00 117.00   1.00   32.95    --  111.85-125.00-120.00   62
 17  ω     51.00 144.00   1.00   32.95    --  111.85 -77.00-150.00   93
 18  ω     36.00  80.00   1.00   32.95    --  111.85 -30.00 -30.00   44
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6276
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.706
_diffrn_reflns_theta_max         75.954
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6276
_reflns_number_gt                5680
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.0156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6276
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.69254(16) 0.60013(13) 0.25250(10) 0.0401(4) Uani 1 1 d . . . . .
N1 N 0.38849(15) 0.50733(11) 0.34731(9) 0.0224(3) Uani 1 1 d . . . . .
N2 N 0.48826(15) 0.56911(11) 0.43583(9) 0.0236(3) Uani 1 1 d . . . . .
N3 N 0.51052(18) 0.53517(13) 0.24170(10) 0.0307(4) Uani 1 1 d . . . . .
N4 N 0.61402(19) 0.56358(14) 0.21232(12) 0.0360(4) Uani 1 1 d . . . . .
C1 C 0.38651(18) 0.52118(12) 0.42069(11) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.49444(18) 0.54627(13) 0.31623(11) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.55638(18) 0.58508(14) 0.37236(12) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.631929 0.617054 0.368781 0.031 Uiso 1 1 calc R U . . .
C4 C 0.29193(18) 0.49140(13) 0.47339(11) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.2206(3) 0.41813(16) 0.46089(14) 0.0368(5) Uani 1 1 d . . . . .
H5 H 0.234637 0.385407 0.417994 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1297(3) 0.39298(18) 0.51054(15) 0.0446(6) Uani 1 1 d . . . . .
H6 H 0.081230 0.343457 0.501092 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1085(2) 0.43908(16) 0.57374(13) 0.0356(5) Uani 1 1 d . . . . .
H7 H 0.046081 0.421429 0.607663 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1790(2) 0.51082(14) 0.58691(12) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.165730 0.542410 0.630513 0.034 Uiso 1 1 calc R U . . .
C9 C 0.26901(18) 0.53738(13) 0.53723(12) 0.0253(4) Uani 1 1 d . . . . .
H9 H 0.315817 0.587609 0.546740 0.030 Uiso 1 1 calc R U . . .
C10 C 0.30802(19) 0.45005(13) 0.30649(11) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.3537(2) 0.36786(14) 0.29386(12) 0.0281(4) Uani 1 1 d . . . . .
C12 C 0.2752(2) 0.31171(15) 0.25675(13) 0.0353(5) Uani 1 1 d . . . . .
H12 H 0.302529 0.255198 0.247722 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1579(2) 0.33745(16) 0.23294(14) 0.0386(5) Uani 1 1 d . . . . .
H13 H 0.105241 0.298294 0.207929 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1162(2) 0.41954(16) 0.24507(14) 0.0350(5) Uani 1 1 d . . . . .
H14 H 0.035913 0.436269 0.227438 0.042 Uiso 1 1 calc R U . . .
C15 C 0.1902(2) 0.47796(14) 0.28270(12) 0.0278(4) Uani 1 1 d . . . . .
C16 C 0.1442(2) 0.56831(15) 0.29599(14) 0.0331(5) Uani 1 1 d . . . . .
H16 H 0.181177 0.588414 0.343218 0.040 Uiso 1 1 calc R U . . .
C17 C 0.0017(3) 0.5745(2) 0.30214(19) 0.0506(7) Uani 1 1 d . . . . .
H17A H -0.036815 0.556559 0.255955 0.076 Uiso 1 1 calc R U . . .
H17B H -0.022241 0.633419 0.312643 0.076 Uiso 1 1 calc R U . . .
H17C H -0.027672 0.537596 0.341788 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1907(3) 0.62739(18) 0.2353(2) 0.0531(7) Uani 1 1 d . . . . .
H18A H 0.282688 0.625231 0.232963 0.080 Uiso 1 1 calc R U . . .
H18B H 0.163668 0.685689 0.245775 0.080 Uiso 1 1 calc R U . . .
H18C H 0.155364 0.609116 0.188376 0.080 Uiso 1 1 calc R U . . .
C19 C 0.4813(2) 0.33862(15) 0.32049(14) 0.0353(5) Uani 1 1 d . . . . .
H19 H 0.524750 0.388564 0.342977 0.042 Uiso 1 1 calc R U . . .
C20 C 0.4698(3) 0.26983(19) 0.37888(18) 0.0550(8) Uani 1 1 d . . . . .
H20A H 0.424739 0.292660 0.421325 0.082 Uiso 1 1 calc R U . . .
H20B H 0.553900 0.251303 0.393870 0.082 Uiso 1 1 calc R U . . .
H20C H 0.423194 0.221321 0.358950 0.082 Uiso 1 1 calc R U . . .
C21 C 0.5620(3) 0.3072(3) 0.25741(19) 0.0621(9) Uani 1 1 d . . . . .
H21A H 0.522404 0.257164 0.235228 0.093 Uiso 1 1 calc R U . . .
H21B H 0.645621 0.291864 0.275679 0.093 Uiso 1 1 calc R U . . .
H21C H 0.569882 0.352172 0.220654 0.093 Uiso 1 1 calc R U . . .
C22 C 0.53972(17) 0.59377(14) 0.50635(11) 0.0247(4) Uani 1 1 d . . . . .
C23 C 0.61573(19) 0.53519(15) 0.54321(12) 0.0291(4) Uani 1 1 d . . . . .
C24 C 0.6736(2) 0.56342(16) 0.60702(13) 0.0316(5) Uani 1 1 d . . . . .
H24 H 0.724817 0.525385 0.634223 0.038 Uiso 1 1 calc R U . . .
C25 C 0.6577(2) 0.64599(17) 0.63155(12) 0.0331(5) Uani 1 1 d . . . . .
H25 H 0.699020 0.664096 0.674918 0.040 Uiso 1 1 calc R U . . .
C26 C 0.58224(19) 0.70244(15) 0.59341(12) 0.0294(4) Uani 1 1 d . . . . .
H26 H 0.572759 0.758971 0.610787 0.035 Uiso 1 1 calc R U . . .
C27 C 0.51998(17) 0.67735(14) 0.52984(12) 0.0252(4) Uani 1 1 d . . . . .
C28 C 0.4342(2) 0.73948(14) 0.48947(12) 0.0287(4) Uani 1 1 d . . . . .
H28 H 0.383405 0.706502 0.453224 0.034 Uiso 1 1 calc R U . . .
C29 C 0.3435(2) 0.78454(18) 0.54113(15) 0.0400(5) Uani 1 1 d . . . . .
H29A H 0.297575 0.742256 0.570028 0.060 Uiso 1 1 calc R U . . .
H29B H 0.283736 0.818423 0.512590 0.060 Uiso 1 1 calc R U . . .
H29C H 0.390930 0.821901 0.573971 0.060 Uiso 1 1 calc R U . . .
C30 C 0.5111(3) 0.80599(18) 0.44751(17) 0.0481(7) Uani 1 1 d . . . . .
H30A H 0.567029 0.835841 0.481504 0.072 Uiso 1 1 calc R U . . .
H30B H 0.454031 0.846904 0.424461 0.072 Uiso 1 1 calc R U . . .
H30C H 0.561406 0.777707 0.409757 0.072 Uiso 1 1 calc R U . . .
C31 C 0.6382(2) 0.44569(16) 0.51575(14) 0.0367(5) Uani 1 1 d . . . . .
H31 H 0.584590 0.436595 0.471484 0.044 Uiso 1 1 calc R U . . .
C32 C 0.6021(5) 0.3795(2) 0.5727(2) 0.0729(12) Uani 1 1 d . . . . .
H32A H 0.657315 0.384881 0.615325 0.109 Uiso 1 1 calc R U . . .
H32B H 0.611040 0.322507 0.551641 0.109 Uiso 1 1 calc R U . . .
H32C H 0.514567 0.388375 0.587705 0.109 Uiso 1 1 calc R U . . .
C33 C 0.7750(4) 0.4354(3) 0.4933(3) 0.0806(13) Uani 1 1 d . . . . .
H33A H 0.797358 0.479812 0.458049 0.121 Uiso 1 1 calc R U . . .
H33B H 0.786995 0.379445 0.470804 0.121 Uiso 1 1 calc R U . . .
H33C H 0.828933 0.440273 0.536576 0.121 Uiso 1 1 calc R 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 N4 1.252(3) . ?
N1 C1 1.359(3) . ?
N1 C2 1.402(3) . ?
N1 C10 1.450(3) . ?
N2 C1 1.347(2) . ?
N2 C3 1.391(3) . ?
N2 C22 1.454(3) . ?
N3 N4 1.303(3) . ?
N3 C2 1.384(3) . ?
C1 C4 1.469(3) . ?
C2 C3 1.364(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.395(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.397(3) . ?
C10 C11 1.401(3) . ?
C11 C12 1.392(3) . ?
C11 C19 1.513(3) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.523(3) . ?
C16 C17 1.523(3) . ?
C16 C18 1.529(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.520(4) . ?
C19 C20 1.525(4) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.399(3) . ?
C22 C27 1.399(3) . ?
C23 C24 1.391(3) . ?
C23 C31 1.514(3) . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.527(3) . ?
C28 C29 1.524(3) . ?
C28 C30 1.534(3) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C33 1.520(4) . ?
C31 C32 1.522(4) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C1 N1 C2 110.01(17) . . ?
C1 N1 C10 126.78(17) . . ?
C2 N1 C10 122.48(17) . . ?
C1 N2 C3 110.36(17) . . ?
C1 N2 C22 129.34(17) . . ?
C3 N2 C22 119.73(16) . . ?
N4 N3 C2 117.82(19) . . ?
O1 N4 N3 118.6(2) . . ?
N2 C1 N1 106.26(17) . . ?
N2 C1 C4 126.39(18) . . ?
N1 C1 C4 127.34(18) . . ?
C3 C2 N3 137.5(2) . . ?
C3 C2 N1 106.18(18) . . ?
N3 C2 N1 116.29(18) . . ?
C2 C3 N2 107.18(17) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C9 C4 C5 118.01(19) . . ?
C9 C4 C1 120.19(18) . . ?
C5 C4 C1 121.79(19) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.88(19) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C15 C10 C11 123.4(2) . . ?
C15 C10 N1 119.61(18) . . ?
C11 C10 N1 117.03(18) . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 C19 120.1(2) . . ?
C10 C11 C19 122.6(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 116.9(2) . . ?
C14 C15 C16 121.0(2) . . ?
C10 C15 C16 122.11(19) . . ?
C17 C16 C15 113.0(2) . . ?
C17 C16 C18 109.6(2) . . ?
C15 C16 C18 110.4(2) . . ?
C17 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C18 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 C21 111.1(2) . . ?
C11 C19 C20 111.6(2) . . ?
C21 C19 C20 110.2(2) . . ?
C11 C19 H19 107.9 . . ?
C21 C19 H19 107.9 . . ?
C20 C19 H19 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 123.93(19) . . ?
C23 C22 N2 117.96(19) . . ?
C27 C22 N2 117.82(19) . . ?
C24 C23 C22 116.7(2) . . ?
C24 C23 C31 120.3(2) . . ?
C22 C23 C31 123.0(2) . . ?
C25 C24 C23 121.2(2) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 120.9(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 116.8(2) . . ?
C26 C27 C28 120.3(2) . . ?
C22 C27 C28 122.89(19) . . ?
C29 C28 C27 112.09(19) . . ?
C29 C28 C30 109.2(2) . . ?
C27 C28 C30 111.11(18) . . ?
C29 C28 H28 108.1 . . ?
C27 C28 H28 108.1 . . ?
C30 C28 H28 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 C33 109.9(2) . . ?
C23 C31 C32 111.7(2) . . ?
C33 C31 C32 110.7(3) . . ?
C23 C31 H31 108.2 . . ?
C33 C31 H31 108.2 . . ?
C32 C31 H31 108.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C2 N3 N4 O1 -0.8(3) . . . . ?
C3 N2 C1 N1 -0.8(2) . . . . ?
C22 N2 C1 N1 -171.87(19) . . . . ?
C3 N2 C1 C4 -179.90(19) . . . . ?
C22 N2 C1 C4 9.0(3) . . . . ?
C2 N1 C1 N2 0.9(2) . . . . ?
C10 N1 C1 N2 171.22(18) . . . . ?
C2 N1 C1 C4 -179.99(19) . . . . ?
C10 N1 C1 C4 -9.7(3) . . . . ?
N4 N3 C2 C3 4.7(4) . . . . ?
N4 N3 C2 N1 -173.62(19) . . . . ?
C1 N1 C2 C3 -0.7(2) . . . . ?
C10 N1 C2 C3 -171.50(18) . . . . ?
C1 N1 C2 N3 178.16(18) . . . . ?
C10 N1 C2 N3 7.3(3) . . . . ?
N3 C2 C3 N2 -178.3(2) . . . . ?
N1 C2 C3 N2 0.2(2) . . . . ?
C1 N2 C3 C2 0.4(2) . . . . ?
C22 N2 C3 C2 172.44(18) . . . . ?
N2 C1 C4 C9 26.9(3) . . . . ?
N1 C1 C4 C9 -152.0(2) . . . . ?
N2 C1 C4 C5 -154.5(2) . . . . ?
N1 C1 C4 C5 26.5(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C1 C4 C5 C6 -178.2(2) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C4 -1.1(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C1 C4 C9 C8 179.09(19) . . . . ?
C1 N1 C10 C15 85.6(3) . . . . ?
C2 N1 C10 C15 -105.1(2) . . . . ?
C1 N1 C10 C11 -93.5(2) . . . . ?
C2 N1 C10 C11 75.7(3) . . . . ?
C15 C10 C11 C12 -1.2(3) . . . . ?
N1 C10 C11 C12 177.98(19) . . . . ?
C15 C10 C11 C19 -179.6(2) . . . . ?
N1 C10 C11 C19 -0.4(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C19 C11 C12 C13 179.2(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C13 C14 C15 C16 180.0(2) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
N1 C10 C15 C14 -178.74(19) . . . . ?
C11 C10 C15 C16 -178.8(2) . . . . ?
N1 C10 C15 C16 2.1(3) . . . . ?
C14 C15 C16 C17 29.9(3) . . . . ?
C10 C15 C16 C17 -151.0(2) . . . . ?
C14 C15 C16 C18 -93.3(3) . . . . ?
C10 C15 C16 C18 85.8(3) . . . . ?
C12 C11 C19 C21 58.7(3) . . . . ?
C10 C11 C19 C21 -122.9(3) . . . . ?
C12 C11 C19 C20 -64.8(3) . . . . ?
C10 C11 C19 C20 113.6(3) . . . . ?
C1 N2 C22 C23 81.3(3) . . . . ?
C3 N2 C22 C23 -89.1(2) . . . . ?
C1 N2 C22 C27 -104.6(2) . . . . ?
C3 N2 C22 C27 85.0(2) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
N2 C22 C23 C24 173.92(19) . . . . ?
C27 C22 C23 C31 -178.5(2) . . . . ?
N2 C22 C23 C31 -4.8(3) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C31 C23 C24 C25 177.7(2) . . . . ?
C23 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C26 C27 C22 -1.2(3) . . . . ?
C25 C26 C27 C28 178.3(2) . . . . ?
C23 C22 C27 C26 0.9(3) . . . . ?
N2 C22 C27 C26 -172.80(17) . . . . ?
C23 C22 C27 C28 -178.62(19) . . . . ?
N2 C22 C27 C28 7.7(3) . . . . ?
C26 C27 C28 C29 -47.8(3) . . . . ?
C22 C27 C28 C29 131.7(2) . . . . ?
C26 C27 C28 C30 74.8(3) . . . . ?
C22 C27 C28 C30 -105.7(2) . . . . ?
C24 C23 C31 C33 -65.7(4) . . . . ?
C22 C23 C31 C33 113.0(3) . . . . ?
C24 C23 C31 C32 57.5(3) . . . . ?
C22 C23 C31 C32 -123.8(3) . . . . ?

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037




_refine_special_details          ', SQUEEZE'
####################################################################### 
# 
# 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 1532913'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        3a_le-5-2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H40 N4 O, 2(C H4 O)'
_chemical_formula_sum            'C35 H48 N4 O3'
_chemical_formula_weight         572.77

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   15.0226(3)
_cell_length_b                   11.73248(17)
_cell_length_c                   19.0842(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.0138(18)
_cell_angle_gamma                90
_cell_volume                     3248.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    10334
_cell_measurement_theta_min      4.3140
_cell_measurement_theta_max      75.8610

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 12 0.0293
1 -1 -12 0.0293
7 -4 4 0.2213
7 0 6 0.1276
-7 5 5 0.2114
-8 1 -5 0.2139
-3 -3 -9 0.1244
-1 -4 -9 0.1443
1 -5 -9 0.1755
-6 -5 8 0.2437
5 6 -4 0.0487
-3 7 0 0.1678
9 1 -6 0.0759
-1 -7 2 0.3022
-7 -5 5 0.2399
7 5 -5 0.0432
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  26.00   1.00    4.05    --  -40.91  38.00   0.00   84
  2  ω    -64.00  22.00   1.00    4.05    --  -40.91  57.00-180.00   86
  3  ω     32.00  86.00   1.00    4.05    --   40.91-125.00 -90.00   54
  4  ω     55.00 101.00   1.00   16.22    --  111.85 -94.00 -60.00   46
  5  ω     83.00 115.00   1.00   16.22    --  111.85-125.00 -90.00   32
  6  ω     78.00 138.00   1.00   16.22    --  111.85 -45.00-120.00   60
  7  ω     91.00 171.00   1.00   16.22    --  111.85  30.00-180.00   80
  8  ω    150.00 176.00   1.00   16.22    --  111.85  61.00-180.00   26
  9  ω    112.00 138.00   1.00   16.22    --  111.85  61.00-180.00   26
 10  ω     98.00 176.00   1.00   16.22    --  111.85  45.00 -90.00   78
 11  ω     88.00 133.00   1.00   16.22    --  111.85  45.00 -30.00   45
 12  ω     82.00 166.00   1.00   16.22    --  111.85  77.00-150.00   84
 13  ω     43.00  70.00   1.00   16.22    --  111.85 -45.00-120.00   27
 14  ω     41.00 134.00   1.00   16.22    --  111.85 -61.00  30.00   93
 15  ω     75.00 105.00   1.00   16.22    --  111.85 -94.00 120.00   30
 16  ω     57.00 122.00   1.00   16.22    --  111.85-125.00  60.00   65
 17  ω     40.00 128.00   1.00   16.22    --  111.85 -61.00 150.00   88
 18  ω     41.00  67.00   1.00   16.22    --  111.85-125.00 150.00   26
 19  ω     30.00  94.00   1.00    4.05    --   40.91-125.00  90.00   64
 20  ω   -129.00 -17.00   1.00    4.05    --  -40.91   0.00   0.00  112
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            22242
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.339
_diffrn_reflns_theta_max         76.152
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6696
_reflns_number_gt                5825
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+1.9191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6696
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.68749(10) 0.29788(12) 0.46717(7) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.50661(10) 0.15561(12) 0.34985(8) 0.0420(4) Uani 1 1 d . . . . .
H2O H 0.535596 0.214105 0.368349 0.063 Uiso 1 1 calc R U . . .
O3 O 0.85630(12) 0.42015(14) 0.49429(8) 0.0513(4) Uani 1 1 d . . . . .
H3O H 0.800620 0.400784 0.484876 0.077 Uiso 1 1 calc R U . . .
N1 N 0.57916(8) 0.58287(10) 0.30965(6) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.45637(8) 0.50678(10) 0.24041(6) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.64501(9) 0.43589(11) 0.39227(7) 0.0224(3) Uani 1 1 d . . . . .
N4 N 0.62574(11) 0.33674(13) 0.41495(8) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.50645(10) 0.60262(12) 0.25201(7) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.57491(10) 0.47152(12) 0.33431(8) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.49678(11) 0.42461(12) 0.29086(8) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.474325 0.349739 0.294514 0.022 Uiso 1 1 calc R U . . .
C4 C 0.48508(10) 0.70814(12) 0.20995(8) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.49660(10) 0.81406(13) 0.24447(8) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.520501 0.818297 0.295618 0.022 Uiso 1 1 calc R U . . .
C6 C 0.47317(11) 0.91325(13) 0.20419(9) 0.0217(3) Uani 1 1 d . . . . .
H6 H 0.481662 0.985222 0.227802 0.026 Uiso 1 1 calc R U . . .
C7 C 0.43737(11) 0.90752(13) 0.12947(9) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.420316 0.975356 0.102104 0.028 Uiso 1 1 calc R U . . .
C8 C 0.42658(12) 0.80236(14) 0.09490(8) 0.0242(3) Uani 1 1 d . . . . .
H8 H 0.402503 0.798540 0.043759 0.029 Uiso 1 1 calc R U . . .
C9 C 0.45075(11) 0.70268(13) 0.13460(8) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.443970 0.631040 0.110602 0.024 Uiso 1 1 calc R U . . .
C10 C 0.64954(10) 0.66492(12) 0.34282(8) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.71385(11) 0.69689(14) 0.30491(9) 0.0230(3) Uani 1 1 d . . . . .
C12 C 0.77736(12) 0.78058(15) 0.33693(11) 0.0323(4) Uani 1 1 d . . . . .
H12 H 0.821989 0.805255 0.312908 0.039 Uiso 1 1 calc R U . . .
C13 C 0.77651(13) 0.82830(16) 0.40307(11) 0.0365(4) Uani 1 1 d . . . . .
H13 H 0.819762 0.886095 0.423480 0.044 Uiso 1 1 calc R U . . .
C14 C 0.71321(13) 0.79256(15) 0.43970(10) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.714379 0.825246 0.485471 0.038 Uiso 1 1 calc R U . . .
C15 C 0.64773(11) 0.70941(13) 0.41066(8) 0.0233(3) Uani 1 1 d . . . . .
C16 C 0.57814(13) 0.67242(14) 0.45165(8) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.540199 0.609531 0.423448 0.033 Uiso 1 1 calc R U . . .
C17 C 0.51286(16) 0.76998(17) 0.45767(11) 0.0407(5) Uani 1 1 d . . . . .
H17A H 0.548537 0.833687 0.484109 0.061 Uiso 1 1 calc R U . . .
H17B H 0.468547 0.743450 0.483786 0.061 Uiso 1 1 calc R U . . .
H17C H 0.479699 0.795273 0.408957 0.061 Uiso 1 1 calc R U . . .
C18 C 0.62637(18) 0.6256(2) 0.52697(10) 0.0468(5) Uani 1 1 d . . . . .
H18A H 0.667209 0.562728 0.521934 0.070 Uiso 1 1 calc R U . . .
H18B H 0.580043 0.597879 0.550773 0.070 Uiso 1 1 calc R U . . .
H18C H 0.662688 0.686317 0.556328 0.070 Uiso 1 1 calc R U . . .
C19 C 0.71725(12) 0.64433(16) 0.23276(9) 0.0278(4) Uani 1 1 d . . . . .
H19 H 0.663786 0.590941 0.217888 0.033 Uiso 1 1 calc R U . . .
C20 C 0.70686(17) 0.7332(2) 0.17315(12) 0.0474(5) Uani 1 1 d . . . . .
H20A H 0.649715 0.776120 0.168805 0.071 Uiso 1 1 calc R U . . .
H20B H 0.704711 0.695228 0.127007 0.071 Uiso 1 1 calc R U . . .
H20C H 0.759465 0.785561 0.185235 0.071 Uiso 1 1 calc R U . . .
C21 C 0.80495(15) 0.5741(2) 0.24014(12) 0.0444(5) Uani 1 1 d . . . . .
H21A H 0.858804 0.624347 0.253352 0.067 Uiso 1 1 calc R U . . .
H21B H 0.802872 0.536590 0.193855 0.067 Uiso 1 1 calc R U . . .
H21C H 0.809363 0.516252 0.277950 0.067 Uiso 1 1 calc R U . . .
C22 C 0.36762(10) 0.49165(12) 0.18874(8) 0.0170(3) Uani 1 1 d . . . . .
C23 C 0.36268(11) 0.41837(12) 0.12972(8) 0.0197(3) Uani 1 1 d . . . . .
C24 C 0.27584(12) 0.40253(14) 0.08215(8) 0.0248(3) Uani 1 1 d . . . . .
H24 H 0.269061 0.352320 0.042051 0.030 Uiso 1 1 calc R U . . .
C25 C 0.19944(12) 0.45908(14) 0.09266(9) 0.0266(4) Uani 1 1 d . . . . .
H25 H 0.140965 0.447436 0.059513 0.032 Uiso 1 1 calc R U . . .
C26 C 0.20703(11) 0.53237(13) 0.15081(9) 0.0234(3) Uani 1 1 d . . . . .
H26 H 0.153900 0.571214 0.156599 0.028 Uiso 1 1 calc R U . . .
C27 C 0.29179(10) 0.54990(12) 0.20103(8) 0.0185(3) Uani 1 1 d . . . . .
C28 C 0.29758(11) 0.62721(13) 0.26601(8) 0.0205(3) Uani 1 1 d . . . . .
H28 H 0.364206 0.638338 0.291129 0.025 Uiso 1 1 calc R U . . .
C29 C 0.25572(13) 0.74453(14) 0.24236(10) 0.0309(4) Uani 1 1 d . . . . .
H29A H 0.286297 0.778283 0.207778 0.046 Uiso 1 1 calc R U . . .
H29B H 0.264361 0.794137 0.284905 0.046 Uiso 1 1 calc R U . . .
H29C H 0.189724 0.736206 0.219254 0.046 Uiso 1 1 calc R U . . .
C30 C 0.25127(14) 0.57101(16) 0.31974(10) 0.0322(4) Uani 1 1 d . . . . .
H30A H 0.185058 0.563226 0.297287 0.048 Uiso 1 1 calc R U . . .
H30B H 0.260840 0.618327 0.363383 0.048 Uiso 1 1 calc R U . . .
H30C H 0.278226 0.495466 0.332985 0.048 Uiso 1 1 calc R U . . .
C31 C 0.44706(12) 0.35956(13) 0.11636(9) 0.0237(3) Uani 1 1 d . . . . .
H31 H 0.503061 0.400054 0.145472 0.028 Uiso 1 1 calc R U . . .
C32 C 0.44786(14) 0.36572(16) 0.03609(10) 0.0333(4) Uani 1 1 d . . . . .
H32A H 0.397866 0.318603 0.007110 0.050 Uiso 1 1 calc R U . . .
H32B H 0.507078 0.337565 0.030556 0.050 Uiso 1 1 calc R U . . .
H32C H 0.439145 0.444933 0.019425 0.050 Uiso 1 1 calc R U . . .
C33 C 0.45305(13) 0.23465(14) 0.14111(10) 0.0306(4) Uani 1 1 d . . . . .
H33A H 0.456188 0.231258 0.192999 0.046 Uiso 1 1 calc R U . . .
H33B H 0.508421 0.199580 0.132408 0.046 Uiso 1 1 calc R U . . .
H33C H 0.398352 0.193380 0.113707 0.046 Uiso 1 1 calc R U . . .
C34 C 0.54483(15) 0.05828(16) 0.39096(10) 0.0369(4) Uani 1 1 d . . . . .
H34A H 0.521252 -0.010897 0.363638 0.055 Uiso 1 1 calc R U . . .
H34B H 0.527488 0.058196 0.437056 0.055 Uiso 1 1 calc R U . . .
H34C H 0.612132 0.060357 0.400572 0.055 Uiso 1 1 calc R U . . .
C35 C 0.86825(14) 0.49913(18) 0.44342(10) 0.0378(4) Uani 1 1 d . . . . .
H35A H 0.865735 0.460272 0.397488 0.057 Uiso 1 1 calc R U . . .
H35B H 0.928242 0.536484 0.461010 0.057 Uiso 1 1 calc R U . . .
H35C H 0.819203 0.556426 0.435811 0.057 Uiso 1 1 calc R 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 N4 1.2580(19) . ?
O2 C34 1.420(2) . ?
O2 H2O 0.8400 . ?
O3 C35 1.387(3) . ?
O3 H3O 0.8400 . ?
N1 C1 1.3544(18) . ?
N1 C2 1.3956(18) . ?
N1 C10 1.4487(19) . ?
N2 C1 1.3390(19) . ?
N2 C3 1.3864(18) . ?
N2 C22 1.4492(18) . ?
N3 N4 1.300(2) . ?
N3 C2 1.3797(19) . ?
C1 C4 1.4650(19) . ?
C2 C3 1.365(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C9 1.398(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.400(2) . ?
C10 C15 1.403(2) . ?
C11 C12 1.395(2) . ?
C11 C19 1.522(2) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.522(2) . ?
C16 C17 1.531(2) . ?
C16 C18 1.534(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.521(3) . ?
C19 C21 1.529(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.399(2) . ?
C22 C23 1.404(2) . ?
C23 C24 1.395(2) . ?
C23 C31 1.522(2) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.521(2) . ?
C28 C30 1.530(2) . ?
C28 C29 1.532(2) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C33 1.535(2) . ?
C31 C32 1.537(2) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 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
C34 O2 H2O 109.5 . . ?
C35 O3 H3O 109.5 . . ?
C1 N1 C2 109.65(12) . . ?
C1 N1 C10 125.80(12) . . ?
C2 N1 C10 124.52(12) . . ?
C1 N2 C3 110.06(12) . . ?
C1 N2 C22 126.42(12) . . ?
C3 N2 C22 123.20(12) . . ?
N4 N3 C2 110.40(13) . . ?
O1 N4 N3 113.96(15) . . ?
N2 C1 N1 106.91(12) . . ?
N2 C1 C4 125.81(13) . . ?
N1 C1 C4 127.28(13) . . ?
C3 C2 N3 136.25(14) . . ?
C3 C2 N1 106.25(12) . . ?
N3 C2 N1 117.50(13) . . ?
C2 C3 N2 107.12(13) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 C9 119.59(13) . . ?
C5 C4 C1 120.73(13) . . ?
C9 C4 C1 119.67(13) . . ?
C6 C5 C4 120.13(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.19(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.81(14) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.45(14) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.81(14) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C11 C10 C15 123.94(15) . . ?
C11 C10 N1 118.40(13) . . ?
C15 C10 N1 117.65(14) . . ?
C12 C11 C10 116.58(16) . . ?
C12 C11 C19 120.15(16) . . ?
C10 C11 C19 123.27(14) . . ?
C13 C12 C11 121.16(18) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.55(16) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.19(17) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 116.54(16) . . ?
C14 C15 C16 120.19(15) . . ?
C10 C15 C16 123.26(15) . . ?
C15 C16 C17 111.34(14) . . ?
C15 C16 C18 111.29(16) . . ?
C17 C16 C18 110.72(15) . . ?
C15 C16 H16 107.8 . . ?
C17 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C11 112.20(16) . . ?
C20 C19 C21 110.95(17) . . ?
C11 C19 C21 111.42(14) . . ?
C20 C19 H19 107.3 . . ?
C11 C19 H19 107.3 . . ?
C21 C19 H19 107.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 123.88(14) . . ?
C27 C22 N2 118.13(13) . . ?
C23 C22 N2 117.98(13) . . ?
C24 C23 C22 116.75(15) . . ?
C24 C23 C31 120.63(14) . . ?
C22 C23 C31 122.62(14) . . ?
C25 C24 C23 120.81(15) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.95(15) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 120.83(15) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 116.76(14) . . ?
C26 C27 C28 119.80(14) . . ?
C22 C27 C28 123.43(13) . . ?
C27 C28 C30 110.46(13) . . ?
C27 C28 C29 111.30(13) . . ?
C30 C28 C29 111.20(14) . . ?
C27 C28 H28 107.9 . . ?
C30 C28 H28 107.9 . . ?
C29 C28 H28 107.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 C33 111.48(14) . . ?
C23 C31 C32 111.57(14) . . ?
C33 C31 C32 109.67(14) . . ?
C23 C31 H31 108.0 . . ?
C33 C31 H31 108.0 . . ?
C32 C31 H31 108.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O3 C35 H35A 109.5 . . ?
O3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
C2 N3 N4 O1 178.91(14) . . . . ?
C3 N2 C1 N1 0.08(16) . . . . ?
C22 N2 C1 N1 173.68(13) . . . . ?
C3 N2 C1 C4 -179.56(14) . . . . ?
C22 N2 C1 C4 -6.0(2) . . . . ?
C2 N1 C1 N2 0.57(16) . . . . ?
C10 N1 C1 N2 -177.57(13) . . . . ?
C2 N1 C1 C4 -179.80(14) . . . . ?
C10 N1 C1 C4 2.1(2) . . . . ?
N4 N3 C2 C3 -8.6(3) . . . . ?
N4 N3 C2 N1 171.73(13) . . . . ?
C1 N1 C2 C3 -1.00(16) . . . . ?
C10 N1 C2 C3 177.17(13) . . . . ?
C1 N1 C2 N3 178.78(13) . . . . ?
C10 N1 C2 N3 -3.1(2) . . . . ?
N3 C2 C3 N2 -178.70(17) . . . . ?
N1 C2 C3 N2 1.01(16) . . . . ?
C1 N2 C3 C2 -0.70(17) . . . . ?
C22 N2 C3 C2 -174.55(13) . . . . ?
N2 C1 C4 C5 138.50(15) . . . . ?
N1 C1 C4 C5 -41.1(2) . . . . ?
N2 C1 C4 C9 -40.0(2) . . . . ?
N1 C1 C4 C9 140.44(15) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C1 C4 C5 C6 -177.85(14) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C4 0.8(2) . . . . ?
C5 C4 C9 C8 -1.4(2) . . . . ?
C1 C4 C9 C8 177.16(14) . . . . ?
C1 N1 C10 C11 -71.66(19) . . . . ?
C2 N1 C10 C11 110.47(16) . . . . ?
C1 N1 C10 C15 107.01(16) . . . . ?
C2 N1 C10 C15 -70.86(19) . . . . ?
C15 C10 C11 C12 -1.9(2) . . . . ?
N1 C10 C11 C12 176.65(14) . . . . ?
C15 C10 C11 C19 177.47(15) . . . . ?
N1 C10 C11 C19 -4.0(2) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C19 C11 C12 C13 -178.97(16) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C13 C14 C15 C16 -179.34(15) . . . . ?
C11 C10 C15 C14 1.8(2) . . . . ?
N1 C10 C15 C14 -176.78(13) . . . . ?
C11 C10 C15 C16 -179.08(14) . . . . ?
N1 C10 C15 C16 2.3(2) . . . . ?
C14 C15 C16 C17 65.3(2) . . . . ?
C10 C15 C16 C17 -113.76(18) . . . . ?
C14 C15 C16 C18 -58.7(2) . . . . ?
C10 C15 C16 C18 122.19(17) . . . . ?
C12 C11 C19 C20 -58.5(2) . . . . ?
C10 C11 C19 C20 122.16(18) . . . . ?
C12 C11 C19 C21 66.6(2) . . . . ?
C10 C11 C19 C21 -112.75(19) . . . . ?
C1 N2 C22 C27 -67.57(19) . . . . ?
C3 N2 C22 C27 105.25(16) . . . . ?
C1 N2 C22 C23 113.12(16) . . . . ?
C3 N2 C22 C23 -74.07(18) . . . . ?
C27 C22 C23 C24 -1.3(2) . . . . ?
N2 C22 C23 C24 177.97(13) . . . . ?
C27 C22 C23 C31 177.74(14) . . . . ?
N2 C22 C23 C31 -3.0(2) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C31 C23 C24 C25 -177.66(14) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C25 C26 C27 C22 1.1(2) . . . . ?
C25 C26 C27 C28 -177.62(14) . . . . ?
C23 C22 C27 C26 0.1(2) . . . . ?
N2 C22 C27 C26 -179.18(13) . . . . ?
C23 C22 C27 C28 178.71(14) . . . . ?
N2 C22 C27 C28 -0.6(2) . . . . ?
C26 C27 C28 C30 70.65(18) . . . . ?
C22 C27 C28 C30 -107.92(17) . . . . ?
C26 C27 C28 C29 -53.38(19) . . . . ?
C22 C27 C28 C29 128.04(16) . . . . ?
C24 C23 C31 C33 -79.69(18) . . . . ?
C22 C23 C31 C33 101.31(17) . . . . ?
C24 C23 C31 C32 43.3(2) . . . . ?
C22 C23 C31 C32 -135.69(15) . . . . ?

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
O2 H2O N4 0.84 2.02 2.848(2) 169.6 .
O3 H3O O1 0.84 2.04 2.842(2) 159.4 .
O3 H3O N3 0.84 2.57 3.271(2) 141.3 .
C3 H3 O2 0.95 2.50 3.341(2) 146.9 .

_refine_diff_density_max         0.762
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.050



_chemical_properties_physical    ', Heat-sensitive'
####################################################################### 
# 
# 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 1532915'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        4_le-5-7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H42 N4 O, C H4 O'
_chemical_formula_sum            'C35 H46 N4 O2'
_chemical_formula_weight         554.76

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

_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                   9.56973(17)
_cell_length_b                   16.6800(3)
_cell_length_c                   20.6981(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.3468(19)
_cell_angle_gamma                90
_cell_volume                     3239.32(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    140.00(10)
_cell_measurement_reflns_used    5121
_cell_measurement_theta_min      4.3310
_cell_measurement_theta_max      75.5700

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 3 9 0.1374
0 -9 8 0.1444
-3 -8 -4 0.1232
-3 1 -11 0.1001
0 9 -8 0.1422
-6 3 2 0.1003
4 2 -12 0.0766
-5 7 3 0.1266
4 -7 6 0.1366
-3 0 13 0.1573
2 6 9 0.1597
4 -8 -4 0.1113
2 -6 9 0.1375
2 -2 -13 0.0925
6 -4 -2 0.0919
3 -5 9 0.1292
4 1 -12 0.0699
6 -2 -8 0.0796
4 7 -8 0.1165
5 -1 6 0.1116
5 5 -1 0.1281
4 7 -6 0.1193
0 10 -3 0.1584
2 3 11 0.1452
-3 7 9 0.1504
-6 -2 -2 0.1135
3 -10 -3 0.1258
1 -5 -12 0.1100
5 3 -8 0.0778
-6 -3 4 0.1296
4 6 7 0.1492
5 1 -11 0.0662
_diffrn_ambient_temperature      140.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  58.00   1.00    1.46    --   40.91  57.00 -60.00   45
  2  ω     92.00 118.00   1.00    5.83    --  111.85 -45.00 -60.00   26
  3  ω     72.00 144.00   1.00    5.83    --  111.85 -77.00-180.00   72
  4  ω     40.00 137.00   1.00    5.83    --  111.85 -61.00   0.00   97
  5  ω     72.00 126.00   1.00    5.83    --  111.85 -45.00 120.00   54
  6  ω     86.00 169.00   1.00    5.83    --  111.85  45.00  90.00   83
  7  ω     87.00 154.00   1.00    5.83    --  111.85  61.00 150.00   67
  8  ω     41.00  88.00   1.00    5.83    --  111.85 -45.00 -60.00   47
  9  ω     25.00  79.00   1.00    1.46    --   40.91-125.00-150.00   54
 10  ω    -69.00 -11.00   1.00    1.46    --  -40.91  57.00  90.00   58
 11  ω   -117.00 -33.00   1.00    1.46    --  -40.91 -77.00 -30.00   84
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            12724
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.357
_diffrn_reflns_theta_max         75.920
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6556
_reflns_number_gt                5329
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0966P)²+0.9652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6556
_refine_ls_number_parameters     408
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_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
O1A O -0.0062(3) 0.24482(17) 0.20945(14) 0.0395(6) Uani 0.5 1 d D U P A 1
O1B O -0.0637(3) 0.33144(18) 0.17082(16) 0.0500(7) Uani 0.5 1 d D U P B 2
N1 N 0.32528(15) 0.30990(8) 0.33900(7) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.29423(15) 0.18641(8) 0.36508(7) 0.0314(3) Uani 1 1 d . . . . .
N3 N 0.14278(18) 0.33306(10) 0.24448(9) 0.0463(4) Uani 1 1 d D . . . .
N4A N 0.0179(7) 0.2995(6) 0.2221(3) 0.0574(19) Uani 0.5 1 d D U P A 1
N4B N 0.0250(8) 0.3149(5) 0.2037(3) 0.0485(15) Uani 0.5 1 d D U P B 2
C1 C 0.37480(18) 0.25179(9) 0.38301(8) 0.0304(3) Uani 1 1 d . . . . .
C2 C 0.20991(18) 0.28114(10) 0.29238(8) 0.0331(3) Uani 1 1 d . . . . .
C3 C 0.19244(18) 0.20282(10) 0.30903(9) 0.0339(3) Uani 1 1 d . . . . .
H3 H 0.123376 0.166452 0.286394 0.041 Uiso 1 1 calc R U . . .
C4 C 0.49191(18) 0.25956(9) 0.43989(9) 0.0325(3) Uani 1 1 d . . . . .
C5 C 0.4740(2) 0.24023(11) 0.50302(10) 0.0427(4) Uani 1 1 d . . . . .
H5 H 0.384904 0.220051 0.509440 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5844(3) 0.25003(11) 0.55664(10) 0.0472(5) Uani 1 1 d . . . . .
H6 H 0.570110 0.235866 0.599325 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7152(2) 0.28010(10) 0.54930(10) 0.0429(4) Uani 1 1 d . . . . .
C8 C 0.7331(2) 0.29885(13) 0.48636(11) 0.0487(5) Uani 1 1 d . . . . .
H8 H 0.822566 0.318800 0.480193 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6235(2) 0.28923(12) 0.43186(10) 0.0420(4) Uani 1 1 d . . . . .
H9 H 0.638311 0.302883 0.389161 0.050 Uiso 1 1 calc R U . . .
C10 C 0.8331(3) 0.29216(14) 0.60852(12) 0.0605(6) Uani 1 1 d . . . . .
H10A H 0.796001 0.283206 0.648814 0.091 Uiso 0.5 1 calc R U P . .
H10B H 0.869655 0.347035 0.608424 0.091 Uiso 0.5 1 calc R U P . .
H10C H 0.910297 0.254086 0.606838 0.091 Uiso 0.5 1 calc R U P . .
H10D H 0.921301 0.306345 0.593903 0.091 Uiso 0.5 1 calc R U P . .
H10E H 0.847647 0.242516 0.634293 0.091 Uiso 0.5 1 calc R U P . .
H10F H 0.807006 0.335465 0.635879 0.091 Uiso 0.5 1 calc R U P . .
C11 C 0.36698(18) 0.39365(9) 0.34700(8) 0.0325(3) Uani 1 1 d . . . . .
C12 C 0.3106(2) 0.43851(10) 0.39300(9) 0.0383(4) Uani 1 1 d . . . . .
C13 C 0.3551(2) 0.51806(11) 0.40189(10) 0.0480(5) Uani 1 1 d . . . . .
H13 H 0.321600 0.550129 0.433618 0.058 Uiso 1 1 calc R U . . .
C14 C 0.4467(3) 0.55095(11) 0.36542(11) 0.0522(5) Uani 1 1 d . . . . .
H14 H 0.475019 0.605398 0.372095 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4975(2) 0.50577(11) 0.31950(11) 0.0458(4) Uani 1 1 d . . . . .
H15 H 0.559436 0.529694 0.294356 0.055 Uiso 1 1 calc R U . . .
C16 C 0.45944(19) 0.42507(10) 0.30920(9) 0.0367(4) Uani 1 1 d . . . . .
C17 C 0.5155(2) 0.37820(11) 0.25692(10) 0.0442(4) Uani 1 1 d . . . . .
H17 H 0.487545 0.320788 0.260095 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6789(3) 0.38206(17) 0.26643(15) 0.0684(7) Uani 1 1 d . . . . .
H18A H 0.708433 0.437605 0.261464 0.103 Uiso 1 1 calc R U . . .
H18B H 0.710577 0.348356 0.233301 0.103 Uiso 1 1 calc R U . . .
H18C H 0.721666 0.362687 0.310595 0.103 Uiso 1 1 calc R U . . .
C19 C 0.4461(3) 0.40906(15) 0.18871(11) 0.0596(6) Uani 1 1 d . . . . .
H19A H 0.342188 0.405360 0.183205 0.089 Uiso 1 1 calc R U . . .
H19B H 0.477949 0.376530 0.154923 0.089 Uiso 1 1 calc R U . . .
H19C H 0.473481 0.465080 0.184210 0.089 Uiso 1 1 calc R U . . .
C20 C 0.2011(2) 0.40475(12) 0.42996(10) 0.0474(5) Uani 1 1 d . . . . .
H20 H 0.205739 0.344970 0.427373 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2294(4) 0.4273(2) 0.50222(13) 0.0861(10) Uani 1 1 d . . . . .
H21A H 0.326676 0.411628 0.522817 0.129 Uiso 1 1 calc R U . . .
H21B H 0.161348 0.399577 0.524117 0.129 Uiso 1 1 calc R U . . .
H21C H 0.218574 0.485400 0.506482 0.129 Uiso 1 1 calc R U . . .
C22 C 0.0516(3) 0.4301(2) 0.39614(14) 0.0757(8) Uani 1 1 d . . . . .
H22A H 0.044093 0.488692 0.397151 0.114 Uiso 1 1 calc R U . . .
H22B H -0.018372 0.406326 0.419224 0.114 Uiso 1 1 calc R U . . .
H22C H 0.032966 0.411694 0.350289 0.114 Uiso 1 1 calc R U . . .
C23 C 0.31019(18) 0.10835(9) 0.39684(8) 0.0313(3) Uani 1 1 d . . . . .
C24 C 0.22407(19) 0.09103(10) 0.44214(9) 0.0361(4) Uani 1 1 d . . . . .
C25 C 0.2370(2) 0.01453(11) 0.46976(9) 0.0413(4) Uani 1 1 d . . . . .
H25 H 0.181161 0.000486 0.501271 0.050 Uiso 1 1 calc R U . . .
C26 C 0.3291(2) -0.04105(10) 0.45220(9) 0.0426(4) Uani 1 1 d . . . . .
H26 H 0.335836 -0.092861 0.471636 0.051 Uiso 1 1 calc R U . . .
C27 C 0.4116(2) -0.02239(10) 0.40680(9) 0.0396(4) Uani 1 1 d . . . . .
H27 H 0.474306 -0.061583 0.395152 0.048 Uiso 1 1 calc R U . . .
C28 C 0.40429(18) 0.05357(9) 0.37756(8) 0.0325(3) Uani 1 1 d . . . . .
C29 C 0.49025(19) 0.07346(10) 0.32547(9) 0.0368(4) Uani 1 1 d . . . . .
H29 H 0.498903 0.133102 0.323329 0.044 Uiso 1 1 calc R U . . .
C30 C 0.6396(3) 0.0384(2) 0.34221(14) 0.0753(8) Uani 1 1 d . . . . .
H30A H 0.684778 0.054071 0.387094 0.113 Uiso 1 1 calc R U . . .
H30B H 0.696141 0.058719 0.311073 0.113 Uiso 1 1 calc R U . . .
H30C H 0.634122 -0.020191 0.339252 0.113 Uiso 1 1 calc R U . . .
C31 C 0.4128(3) 0.04406(15) 0.25851(10) 0.0549(5) Uani 1 1 d . . . . .
H31A H 0.398916 -0.014066 0.260127 0.082 Uiso 1 1 calc R U . . .
H31B H 0.469508 0.056657 0.225246 0.082 Uiso 1 1 calc R U . . .
H31C H 0.319841 0.070620 0.246964 0.082 Uiso 1 1 calc R U . . .
C32 C 0.1155(2) 0.14964(12) 0.45914(11) 0.0484(5) Uani 1 1 d . . . . .
H32 H 0.144455 0.204802 0.448156 0.058 Uiso 1 1 calc R U . . .
C33 C 0.1080(3) 0.14836(16) 0.53197(13) 0.0701(8) Uani 1 1 d . . . . .
H33A H 0.068668 0.096940 0.542794 0.105 Uiso 1 1 calc R U . . .
H33B H 0.046477 0.192064 0.541378 0.105 Uiso 1 1 calc R U . . .
H33C H 0.203868 0.155270 0.558596 0.105 Uiso 1 1 calc R U . . .
C34 C -0.0312(3) 0.13234(15) 0.41667(14) 0.0631(6) Uani 1 1 d . . . . .
H34A H -0.027188 0.139573 0.370082 0.095 Uiso 1 1 calc R U . . .
H34B H -0.101436 0.169333 0.428674 0.095 Uiso 1 1 calc R U . . .
H34C H -0.058821 0.077032 0.424058 0.095 Uiso 1 1 calc R U . . .
O2 O 0.3334(6) 0.3358(3) 0.7375(3) 0.1124(17) Uani 0.5 1 d D U P C 1
H2O H 0.391424 0.303063 0.726640 0.169 Uiso 0.5 1 calc R U P C 1
O3 O 0.2326(4) 0.2892(2) 0.64046(17) 0.0632(9) Uani 0.5 1 d D U P D 2
H3O H 0.303836 0.260488 0.655300 0.095 Uiso 0.5 1 calc R U P D 2
C35 C 0.2041(3) 0.3361(2) 0.68821(18) 0.0861(9) Uani 0.5 1 d D U P C 1
H35A H 0.124730 0.317542 0.707888 0.129 Uiso 0.5 1 calc R U P C 1
H35B H 0.215066 0.300197 0.652030 0.129 Uiso 0.5 1 calc R U P C 1
H35C H 0.184632 0.390590 0.671202 0.129 Uiso 0.5 1 calc R U P C 1
C36 C 0.2041(3) 0.3361(2) 0.68821(18) 0.0861(9) Uani 0.5 1 d D U P D 2
H36A H 0.293483 0.356609 0.714425 0.129 Uiso 0.5 1 calc R U P D 2
H36B H 0.153453 0.305059 0.716617 0.129 Uiso 0.5 1 calc R U P D 2
H36C H 0.144514 0.381056 0.668785 0.129 Uiso 0.5 1 calc R U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A N4A 0.965(8) . ?
O1B N4B 1.017(7) . ?
N1 C1 1.351(2) . ?
N1 C2 1.400(2) . ?
N1 C11 1.4533(19) . ?
N2 C1 1.345(2) . ?
N2 C3 1.387(2) . ?
N2 C23 1.4529(19) . ?
N3 N4B 1.304(5) . ?
N3 N4A 1.318(6) . ?
N3 C2 1.377(2) . ?
C1 C4 1.463(2) . ?
C2 C3 1.370(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 C9 1.393(2) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C10 1.507(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C11 C16 1.394(2) . ?
C11 C12 1.400(2) . ?
C12 C13 1.395(3) . ?
C12 C20 1.522(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.516(3) . ?
C17 C19 1.527(3) . ?
C17 C18 1.538(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.514(3) . ?
C20 C22 1.524(3) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.395(2) . ?
C23 C28 1.395(2) . ?
C24 C25 1.394(2) . ?
C24 C32 1.518(3) . ?
C25 C26 1.377(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.400(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.516(2) . ?
C29 C31 1.519(3) . ?
C29 C30 1.520(3) . ?
C29 H29 1.0000 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.524(3) . ?
C32 C34 1.530(4) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O2 C35 1.440(5) . ?
O2 H2O 0.8400 . ?
O3 C36 1.330(4) . ?
O3 H3O 0.8400 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C1 N1 C2 110.08(13) . . ?
C1 N1 C11 124.12(14) . . ?
C2 N1 C11 124.71(14) . . ?
C1 N2 C3 109.92(13) . . ?
C1 N2 C23 126.75(14) . . ?
C3 N2 C23 123.30(14) . . ?
N4B N3 C2 122.7(4) . . ?
N4A N3 C2 104.4(4) . . ?
O1A N4A N3 130.4(9) . . ?
O1B N4B N3 150.7(8) . . ?
N2 C1 N1 106.85(15) . . ?
N2 C1 C4 126.92(14) . . ?
N1 C1 C4 126.22(14) . . ?
C3 C2 N3 135.93(18) . . ?
C3 C2 N1 105.78(15) . . ?
N3 C2 N1 118.28(15) . . ?
C2 C3 N2 107.35(15) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
C5 C4 C9 118.45(18) . . ?
C5 C4 C1 121.32(16) . . ?
C9 C4 C1 120.19(16) . . ?
C6 C5 C4 120.76(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.27(19) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.87(19) . . ?
C8 C7 C10 121.6(2) . . ?
C6 C7 C10 120.5(2) . . ?
C7 C8 C9 121.64(19) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 119.99(18) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
C7 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
C7 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C16 C11 C12 123.57(15) . . ?
C16 C11 N1 119.21(14) . . ?
C12 C11 N1 117.22(14) . . ?
C13 C12 C11 116.76(17) . . ?
C13 C12 C20 120.52(17) . . ?
C11 C12 C20 122.66(16) . . ?
C14 C13 C12 121.11(18) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.67(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.03(18) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 116.82(17) . . ?
C11 C16 C17 124.04(15) . . ?
C15 C16 C17 119.11(16) . . ?
C16 C17 C19 109.60(17) . . ?
C16 C17 C18 112.38(19) . . ?
C19 C17 C18 110.54(18) . . ?
C16 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C12 113.4(2) . . ?
C21 C20 C22 110.7(2) . . ?
C12 C20 C22 110.08(17) . . ?
C21 C20 H20 107.4 . . ?
C12 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 123.81(15) . . ?
C24 C23 N2 117.79(14) . . ?
C28 C23 N2 118.29(14) . . ?
C25 C24 C23 116.68(16) . . ?
C25 C24 C32 120.27(16) . . ?
C23 C24 C32 122.99(16) . . ?
C26 C25 C24 121.19(17) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 120.73(16) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 120.87(17) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C23 C28 C27 116.71(16) . . ?
C23 C28 C29 122.08(15) . . ?
C27 C28 C29 121.17(15) . . ?
C28 C29 C31 110.03(15) . . ?
C28 C29 C30 111.79(16) . . ?
C31 C29 C30 110.62(19) . . ?
C28 C29 H29 108.1 . . ?
C31 C29 H29 108.1 . . ?
C30 C29 H29 108.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C24 C32 C33 112.8(2) . . ?
C24 C32 C34 109.75(17) . . ?
C33 C32 C34 110.44(19) . . ?
C24 C32 H32 107.9 . . ?
C33 C32 H32 107.9 . . ?
C34 C32 H32 107.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 O2 H2O 109.5 . . ?
C36 O3 H3O 109.5 . . ?
O2 C35 H35A 109.5 . . ?
O2 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O2 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O3 C36 H36A 109.5 . . ?
O3 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O3 C36 H36C 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
C2 N3 N4A O1A -46.3(9) . . . . ?
C2 N3 N4B O1B 162.0(13) . . . . ?
C3 N2 C1 N1 0.12(18) . . . . ?
C23 N2 C1 N1 178.30(14) . . . . ?
C3 N2 C1 C4 178.99(15) . . . . ?
C23 N2 C1 C4 -2.8(3) . . . . ?
C2 N1 C1 N2 0.52(17) . . . . ?
C11 N1 C1 N2 169.06(14) . . . . ?
C2 N1 C1 C4 -178.37(15) . . . . ?
C11 N1 C1 C4 -9.8(2) . . . . ?
N4B N3 C2 C3 6.9(6) . . . . ?
N4A N3 C2 C3 17.6(5) . . . . ?
N4B N3 C2 N1 -171.9(5) . . . . ?
N4A N3 C2 N1 -161.1(4) . . . . ?
C1 N1 C2 C3 -0.94(17) . . . . ?
C11 N1 C2 C3 -169.41(14) . . . . ?
C1 N1 C2 N3 178.17(14) . . . . ?
C11 N1 C2 N3 9.7(2) . . . . ?
N3 C2 C3 N2 -177.90(19) . . . . ?
N1 C2 C3 N2 0.98(17) . . . . ?
C1 N2 C3 C2 -0.71(18) . . . . ?
C23 N2 C3 C2 -178.97(14) . . . . ?
N2 C1 C4 C5 -53.0(2) . . . . ?
N1 C1 C4 C5 125.69(18) . . . . ?
N2 C1 C4 C9 129.09(18) . . . . ?
N1 C1 C4 C9 -52.2(2) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C1 C4 C5 C6 -178.12(16) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 C10 178.56(18) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C10 C7 C8 C9 -178.70(18) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C1 C4 C9 C8 178.00(16) . . . . ?
C1 N1 C11 C16 105.86(19) . . . . ?
C2 N1 C11 C16 -87.3(2) . . . . ?
C1 N1 C11 C12 -74.2(2) . . . . ?
C2 N1 C11 C12 92.7(2) . . . . ?
C16 C11 C12 C13 -2.1(3) . . . . ?
N1 C11 C12 C13 177.91(17) . . . . ?
C16 C11 C12 C20 175.22(18) . . . . ?
N1 C11 C12 C20 -4.7(3) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C20 C12 C13 C14 -175.5(2) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
N1 C11 C16 C15 -179.20(16) . . . . ?
C12 C11 C16 C17 -176.93(18) . . . . ?
N1 C11 C16 C17 3.0(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C14 C15 C16 C17 178.6(2) . . . . ?
C11 C16 C17 C19 108.6(2) . . . . ?
C15 C16 C17 C19 -69.1(2) . . . . ?
C11 C16 C17 C18 -128.1(2) . . . . ?
C15 C16 C17 C18 54.2(2) . . . . ?
C13 C12 C20 C21 -44.9(3) . . . . ?
C11 C12 C20 C21 137.8(2) . . . . ?
C13 C12 C20 C22 79.8(3) . . . . ?
C11 C12 C20 C22 -97.5(2) . . . . ?
C1 N2 C23 C24 97.0(2) . . . . ?
C3 N2 C23 C24 -85.1(2) . . . . ?
C1 N2 C23 C28 -86.7(2) . . . . ?
C3 N2 C23 C28 91.3(2) . . . . ?
C28 C23 C24 C25 1.2(3) . . . . ?
N2 C23 C24 C25 177.28(16) . . . . ?
C28 C23 C24 C32 -175.92(18) . . . . ?
N2 C23 C24 C32 0.2(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C32 C24 C25 C26 176.34(19) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C26 C27 C28 0.2(3) . . . . ?
C24 C23 C28 C27 -0.8(3) . . . . ?
N2 C23 C28 C27 -176.88(15) . . . . ?
C24 C23 C28 C29 176.70(16) . . . . ?
N2 C23 C28 C29 0.6(2) . . . . ?
C26 C27 C28 C23 0.0(3) . . . . ?
C26 C27 C28 C29 -177.46(17) . . . . ?
C23 C28 C29 C31 -94.6(2) . . . . ?
C27 C28 C29 C31 82.8(2) . . . . ?
C23 C28 C29 C30 142.1(2) . . . . ?
C27 C28 C29 C30 -40.6(3) . . . . ?
C25 C24 C32 C33 41.4(3) . . . . ?
C23 C24 C32 C33 -141.6(2) . . . . ?
C25 C24 C32 C34 -82.2(2) . . . . ?
C23 C24 C32 C34 94.8(2) . . . . ?

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
O2 H2O O1A 0.84 1.36 2.203(6) 175.1 4_666
O2 H2O N4A 0.84 2.11 2.922(9) 162.7 4_666
O3 H3O O1B 0.84 1.97 2.785(4) 161.9 4_666
O3 H3O N4B 0.84 2.50 3.334(6) 175.4 4_666

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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 1532916'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        5_LE-5-69
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C78 H102 K2 N12 O9'
_chemical_formula_sum            'C78 H102 K2 N12 O9'
_chemical_formula_weight         1429.91

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   16.89427(17)
_cell_length_b                   12.89091(13)
_cell_length_c                   20.8753(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.3465(12)
_cell_angle_gamma                90
_cell_volume                     4289.55(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    15448
_cell_measurement_theta_min      3.4040
_cell_measurement_theta_max      75.4410

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -2 13 0.1604
10 3 -2 0.1712
9 2 4 0.2187
2 0 12 0.2355
11 0 -3 0.1651
4 -8 -4 0.1011
3 -8 0 0.0885
-6 5 9 0.1139
-2 7 -7 0.1354
-8 3 10 0.1299
-6 7 0 0.1071
-1 -2 -12 0.1954
7 5 4 0.2062
9 5 -4 0.1444
1 2 12 0.2304
-8 -4 9 0.1494
-9 -5 4 0.1514
-8 -5 0 0.1588
10 0 -10 0.1221
8 4 -9 0.1131
1 3 -12 0.1759
-9 -1 11 0.1554
-2 8 0 0.0666
9 -4 -3 0.1287
-5 -2 13 0.1587
7 -6 -1 0.1189
4 -4 9 0.2194
-1 -7 7 0.1216
-10 -1 0 0.1755
-6 -7 4 0.1246
-4 8 0 0.0796
9 -1 3 0.2159
-2 1 -12 0.1911
8 2 -11 0.1361
3 7 5 0.1719
3 8 -3 0.0829
10 2 -8 0.1364
0 5 10 0.1985
0 -8 -3 0.1169
-4 -7 7 0.1229
-2 -8 1 0.1086
0 8 -1 0.0709
1 -8 0 0.0937
-7 5 9 0.1111
0 -5 10 0.1672
-3 -7 -5 0.1559
-6 -7 1 0.1278
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  25.00   1.00    3.00    --   41.04 -57.00  90.00   56
  2  ω     33.00  60.00   1.00    3.00    --   41.04-125.00  60.00   27
  3  ω     33.00  97.00   1.00    3.00    --   41.04-125.00  90.00   64
  4  ω     62.00 106.00   1.00   12.00    --  111.85 -94.00 -60.00   44
  5  ω     93.00 122.00   1.00   12.00    --  111.85-125.00-120.00   29
  6  ω     70.00  95.00   1.00   12.00    --  111.85 -94.00   0.00   25
  7  ω     44.00 131.00   1.00   12.00    --  111.85 -45.00 -90.00   87
  8  ω     85.00 156.00   1.00   12.00    --  111.85  30.00 -90.00   71
  9  ω     97.00 175.00   1.00   12.00    --  111.85  45.00   0.00   78
 10  ω    104.00 178.00   1.00   12.00    --  111.85 125.00-120.00   74
 11  ω    109.00 151.00   1.00   12.00    --  111.85 125.00-150.00   42
 12  ω     92.00 173.00   1.00   12.00    --  111.85  61.00 -60.00   81
 13  ω     99.00 173.00   1.00   12.00    --  111.85 125.00-180.00   74
 14  ω     50.00 125.00   1.00   12.00    --  111.85 -61.00-180.00   75
 15  ω     45.00  81.00   1.00    3.00    --   41.04-125.00-180.00   36
 16  ω     32.00  92.00   1.00   12.00    --  111.85 -94.00-180.00   60
 17  ω     39.00  67.00   1.00   12.00    --  111.85-125.00-120.00   28
 18  ω     89.00 120.00   1.00   12.00    --  111.85-125.00 120.00   31
 19  ω    -67.00  32.00   1.00    3.00    --  -41.04  57.00   0.00   99
 20  ω   -109.00 -27.00   1.00    3.00    --  -41.04 -38.00 120.00   82
 21  ω   -113.00  -9.00   1.00    3.00    --  -41.04 -77.00-120.00  104
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            30509
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.932
_diffrn_reflns_theta_max         76.053
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8828
_reflns_number_gt                8154
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1089P)²+8.3281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8828
_refine_ls_number_parameters     537
_refine_ls_number_restraints     245
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2284
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
K1A K 0.86343(13) 0.1477(2) 0.23905(10) 0.0646(5) Uani 0.742(3) 1 d D . P A 1
O1A O 0.52099(18) 0.3199(3) 0.30547(15) 0.0457(7) Uani 0.742(3) 1 d D . P A 1
O2A O 0.80178(17) 0.0796(2) 0.33513(13) 0.0342(6) Uani 0.742(3) 1 d D . P A 1
O3A O 0.9488(4) 0.0005(5) 0.1809(3) 0.0989(16) Uani 0.742(3) 1 d D U P A 1
C34A C 1.0269(4) -0.0305(7) 0.2172(4) 0.0922(19) Uani 0.742(3) 1 d D U P A 1
H34A H 1.035379 -0.104246 0.208071 0.111 Uiso 0.742(3) 1 calc R U P A 1
H34B H 1.037343 -0.021571 0.266420 0.111 Uiso 0.742(3) 1 calc R U P A 1
C35A C 1.0840(6) 0.0386(8) 0.1937(4) 0.109(2) Uani 0.742(3) 1 d D U P A 1
H35A H 1.132755 -0.000808 0.190405 0.130 Uiso 0.742(3) 1 calc R U P A 1
H35B H 1.104421 0.097558 0.225257 0.130 Uiso 0.742(3) 1 calc R U P A 1
C36A C 1.0293(4) 0.0759(7) 0.1248(4) 0.095(2) Uani 0.742(3) 1 d D U P A 1
H36A H 1.052336 0.054025 0.089062 0.114 Uiso 0.742(3) 1 calc R U P A 1
H36B H 1.024015 0.152436 0.123922 0.114 Uiso 0.742(3) 1 calc R U P A 1
C37A C 0.9456(5) 0.0246(8) 0.1152(4) 0.094(2) Uani 0.742(3) 1 d D U P A 1
H37A H 0.898665 0.072596 0.093264 0.113 Uiso 0.742(3) 1 calc R U P A 1
H37B H 0.938887 -0.038809 0.087110 0.113 Uiso 0.742(3) 1 calc R U P A 1
C38A C 0.7849(6) 0.3860(5) 0.3085(3) 0.089(2) Uani 0.742(3) 1 d D U P A 1
H38A H 0.747392 0.389116 0.336174 0.107 Uiso 0.742(3) 1 calc R U P A 1
H38B H 0.840809 0.361523 0.337646 0.107 Uiso 0.742(3) 1 calc R U P A 1
C39A C 0.7917(5) 0.4890(5) 0.2800(4) 0.0685(19) Uani 0.742(3) 1 d D U P A 1
H39A H 0.841001 0.493859 0.264533 0.082 Uiso 0.742(3) 1 calc R U P A 1
H39B H 0.793871 0.545498 0.312721 0.082 Uiso 0.742(3) 1 calc R U P A 1
K1B K 0.8632(4) 0.1416(6) 0.2507(4) 0.0646(5) Uani 0.258(3) 1 d D . P A 2
O1B O 0.6304(5) 0.3422(7) 0.3159(4) 0.0457(7) Uani 0.258(3) 1 d D . P A 2
O2B O 0.8606(4) 0.1933(6) 0.3781(4) 0.0342(6) Uani 0.258(3) 1 d D . P A 2
O3B O 0.9421(9) -0.0375(11) 0.2100(8) 0.091(3) Uani 0.258(3) 1 d D U P A 2
C34B C 0.9883(14) 0.0540(15) 0.2285(11) 0.094(3) Uani 0.258(3) 1 d D U P A 2
H34C H 1.036431 0.049358 0.271283 0.113 Uiso 0.258(3) 1 calc R U P A 2
H34D H 0.954123 0.116769 0.227387 0.113 Uiso 0.258(3) 1 calc R U P A 2
C35B C 1.0105(14) 0.036(2) 0.1642(10) 0.098(3) Uani 0.258(3) 1 d D U P A 2
H35C H 1.053541 -0.019607 0.174979 0.118 Uiso 0.258(3) 1 calc R U P A 2
H35D H 1.038273 0.099759 0.156262 0.118 Uiso 0.258(3) 1 calc R U P A 2
C36B C 0.9448(16) 0.007(2) 0.0964(10) 0.094(3) Uani 0.258(3) 1 d D U P A 2
H36C H 0.908735 0.064930 0.072546 0.113 Uiso 0.258(3) 1 calc R U P A 2
H36D H 0.966795 -0.033416 0.065487 0.113 Uiso 0.258(3) 1 calc R U P A 2
C37B C 0.9081(12) -0.0589(17) 0.1404(8) 0.081(3) Uani 0.258(3) 1 d D U P A 2
H37C H 0.846723 -0.047308 0.125553 0.097 Uiso 0.258(3) 1 calc R U P A 2
H37D H 0.917542 -0.133020 0.132861 0.097 Uiso 0.258(3) 1 calc R U P A 2
C38B C 0.8217(9) 0.3777(12) 0.2946(10) 0.059(3) Uani 0.258(3) 1 d D U P A 2
H38C H 0.844143 0.350684 0.341520 0.071 Uiso 0.258(3) 1 calc R U P A 2
H38D H 0.867467 0.386858 0.275280 0.071 Uiso 0.258(3) 1 calc R U P A 2
C39B C 0.7697(16) 0.4717(15) 0.2887(3) 0.077(4) Uani 0.258(3) 1 d D U P A 2
H39C H 0.803940 0.534455 0.305926 0.092 Uiso 0.258(3) 1 calc R U P A 2
H39D H 0.727285 0.463647 0.311668 0.092 Uiso 0.258(3) 1 calc R U P A 2
O4 O 0.750000 0.3152(3) 0.250000 0.0948(18) Uani 1 2 d DS TU P . .
O5 O 1.0361(3) 0.2041(3) 0.2998(2) 0.0957(12) Uani 1 1 d D . . . .
N1 N 0.81774(12) 0.24657(16) 0.50511(10) 0.0202(4) Uani 1 1 d . . . . .
N2 N 0.72440(12) 0.36193(16) 0.50610(11) 0.0223(4) Uani 1 1 d . . . . .
N3 N 0.61030(15) 0.3306(2) 0.40532(13) 0.0370(6) Uani 1 1 d . . . . .
N4 N 0.59155(19) 0.2988(3) 0.34389(15) 0.0548(8) Uani 1 1 d D . . . .
N5 N 0.74135(14) 0.15700(19) 0.39612(12) 0.0313(5) Uani 1 1 d . . . . .
N6 N 0.80694(17) 0.1436(2) 0.37881(13) 0.0390(6) Uani 1 1 d D . . . .
C1 C 0.80087(14) 0.32399(19) 0.54195(12) 0.0206(5) Uani 1 1 d . . . . .
C2 C 0.69130(15) 0.3067(2) 0.44567(13) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.75037(14) 0.23419(19) 0.44433(12) 0.0221(5) Uani 1 1 d . . . . .
C4 C 0.85671(14) 0.3664(2) 0.60637(12) 0.0226(5) Uani 1 1 d . . . . .
C5 C 0.90495(16) 0.3027(2) 0.65868(13) 0.0286(6) Uani 1 1 d . . . . .
H5 H 0.900859 0.229343 0.654166 0.034 Uiso 1 1 calc R U . . .
C6 C 0.95937(19) 0.3475(3) 0.71781(14) 0.0370(7) Uani 1 1 d . . . . .
H6 H 0.992748 0.304146 0.753336 0.044 Uiso 1 1 calc R U . . .
C7 C 0.96526(18) 0.4538(3) 0.72529(14) 0.0376(7) Uani 1 1 d . . . . .
H7 H 1.002208 0.483366 0.765889 0.045 Uiso 1 1 calc R U . . .
C8 C 0.91729(18) 0.5173(2) 0.67359(15) 0.0336(6) Uani 1 1 d . . . . .
H8 H 0.921239 0.590566 0.678721 0.040 Uiso 1 1 calc R U . . .
C9 C 0.86352(16) 0.4743(2) 0.61436(14) 0.0274(5) Uani 1 1 d . . . . .
H9 H 0.830996 0.518303 0.578868 0.033 Uiso 1 1 calc R U . . .
C10 C 0.88953(15) 0.17761(19) 0.52987(12) 0.0230(5) Uani 1 1 d . . . . .
C11 C 0.96813(15) 0.2127(2) 0.53115(13) 0.0252(5) Uani 1 1 d . . . . .
C12 C 1.03559(17) 0.1451(2) 0.55876(15) 0.0338(6) Uani 1 1 d . . . . .
H12 H 1.090185 0.165926 0.560476 0.041 Uiso 1 1 calc R U . . .
C13 C 1.0249(2) 0.0489(3) 0.58355(16) 0.0398(7) Uani 1 1 d . . . . .
H13 H 1.071794 0.004430 0.602010 0.048 Uiso 1 1 calc R U . . .
C14 C 0.9462(2) 0.0171(2) 0.58158(16) 0.0385(7) Uani 1 1 d . . . . .
H14 H 0.939493 -0.049286 0.598855 0.046 Uiso 1 1 calc R U . . .
C15 C 0.87630(18) 0.0806(2) 0.55474(14) 0.0299(6) Uani 1 1 d . . . . .
C16 C 0.98266(16) 0.3173(2) 0.50379(15) 0.0300(6) Uani 1 1 d . . . . .
H16 H 0.928138 0.355702 0.488918 0.036 Uiso 1 1 calc R U . . .
C17 C 1.0102(2) 0.3017(3) 0.44158(17) 0.0434(7) Uani 1 1 d . . . . .
H17A H 1.064716 0.266625 0.455295 0.065 Uiso 1 1 calc R U . . .
H17B H 1.014906 0.369285 0.421655 0.065 Uiso 1 1 calc R U . . .
H17C H 0.968553 0.259184 0.407974 0.065 Uiso 1 1 calc R U . . .
C18 C 1.04632(18) 0.3819(3) 0.55891(18) 0.0387(7) Uani 1 1 d . . . . .
H18A H 1.024423 0.395000 0.596150 0.058 Uiso 1 1 calc R U . . .
H18B H 1.055815 0.448135 0.539560 0.058 Uiso 1 1 calc R U . . .
H18C H 1.099391 0.343861 0.576215 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7903(2) 0.0434(2) 0.55370(19) 0.0421(7) Uani 1 1 d . . . . .
H19 H 0.748336 0.098409 0.531703 0.050 Uiso 1 1 calc R U . . .
C20 C 0.7880(3) 0.0260(4) 0.6254(3) 0.0675(13) Uani 1 1 d . . . . .
H20A H 0.828430 -0.028079 0.647901 0.101 Uiso 1 1 calc R U . . .
H20B H 0.731496 0.004179 0.623085 0.101 Uiso 1 1 calc R U . . .
H20C H 0.802499 0.090661 0.651364 0.101 Uiso 1 1 calc R U . . .
C21 C 0.7662(3) -0.0556(3) 0.5105(3) 0.0776(15) Uani 1 1 d . . . . .
H21A H 0.768106 -0.041998 0.464890 0.116 Uiso 1 1 calc R U . . .
H21B H 0.709330 -0.076841 0.507438 0.116 Uiso 1 1 calc R U . . .
H21C H 0.805784 -0.111195 0.531766 0.116 Uiso 1 1 calc R U . . .
C22 C 0.67404(14) 0.4308(2) 0.53166(13) 0.0247(5) Uani 1 1 d . . . . .
C23 C 0.66188(15) 0.5330(2) 0.50897(14) 0.0267(5) Uani 1 1 d . . . . .
C24 C 0.61019(16) 0.5942(2) 0.53360(16) 0.0347(6) Uani 1 1 d . . . . .
H24 H 0.600466 0.664387 0.519342 0.042 Uiso 1 1 calc R U . . .
C25 C 0.57285(17) 0.5552(3) 0.57813(17) 0.0389(7) Uani 1 1 d . . . . .
H25 H 0.537854 0.598489 0.594123 0.047 Uiso 1 1 calc R U . . .
C26 C 0.58638(17) 0.4532(3) 0.59950(16) 0.0376(7) Uani 1 1 d . . . . .
H26 H 0.561093 0.427255 0.630697 0.045 Uiso 1 1 calc R U . . .
C27 C 0.63640(16) 0.3878(2) 0.57607(14) 0.0306(6) Uani 1 1 d . . . . .
C28 C 0.70044(16) 0.5775(2) 0.45866(15) 0.0300(6) Uani 1 1 d . . . . .
H28 H 0.744331 0.528028 0.454979 0.036 Uiso 1 1 calc R U . . .
C29 C 0.63416(19) 0.5888(3) 0.38807(17) 0.0409(7) Uani 1 1 d . . . . .
H29A H 0.607706 0.521397 0.373060 0.061 Uiso 1 1 calc R U . . .
H29B H 0.661001 0.613424 0.355863 0.061 Uiso 1 1 calc R U . . .
H29C H 0.591427 0.638843 0.390202 0.061 Uiso 1 1 calc R U . . .
C30 C 0.74237(19) 0.6825(2) 0.48176(19) 0.0410(7) Uani 1 1 d . . . . .
H30A H 0.699647 0.733718 0.482078 0.061 Uiso 1 1 calc R U . . .
H30B H 0.771151 0.705117 0.450416 0.061 Uiso 1 1 calc R U . . .
H30C H 0.783167 0.675875 0.527575 0.061 Uiso 1 1 calc R U . . .
C31 C 0.64558(18) 0.2745(3) 0.59608(16) 0.0380(7) Uani 1 1 d . . . . .
H31 H 0.692088 0.246077 0.581601 0.046 Uiso 1 1 calc R U . . .
C32 C 0.6713(4) 0.2600(5) 0.6716(2) 0.0880(17) Uani 1 1 d . . . . .
H32A H 0.723877 0.297287 0.693621 0.132 Uiso 1 1 calc R U . . .
H32B H 0.679373 0.186013 0.682484 0.132 Uiso 1 1 calc R U . . .
H32C H 0.627386 0.287423 0.688029 0.132 Uiso 1 1 calc R U . . .
C33 C 0.5672(3) 0.2140(3) 0.5578(3) 0.0689(13) Uani 1 1 d . . . . .
H33A H 0.520431 0.237435 0.572067 0.103 Uiso 1 1 calc R U . . .
H33B H 0.577020 0.139910 0.567672 0.103 Uiso 1 1 calc R U . . .
H33C H 0.553554 0.225694 0.508943 0.103 Uiso 1 1 calc R 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
K1A O2A 2.695(3) . ?
K1A N5 2.793(3) 2_655 ?
K1A O2A 2.845(3) 2_655 ?
K1A O5 2.862(5) . ?
K1A N4 2.871(4) 2_655 ?
K1A O3A 2.884(5) . ?
K1A O4 2.946(4) . ?
K1A N6 3.106(4) 2_655 ?
K1A O1A 3.287(4) 2_655 ?
K1A N6 3.357(3) . ?
K1A K1A 4.008(4) 2_655 ?
O1A N4 1.227(4) . ?
O2A N6 1.211(3) . ?
O3A C34A 1.345(7) . ?
O3A C37A 1.391(8) . ?
C34A C35A 1.508(8) . ?
C34A H34A 0.9900 . ?
C34A H34B 0.9900 . ?
C35A C36A 1.508(8) . ?
C35A H35A 0.9900 . ?
C35A H35B 0.9900 . ?
C36A C37A 1.513(8) . ?
C36A H36A 0.9900 . ?
C36A H36B 0.9900 . ?
C37A H37A 0.9900 . ?
C37A H37B 0.9900 . ?
C38A C39A 1.475(8) . ?
C38A O4 1.481(6) . ?
C38A H38A 0.9900 . ?
C38A H38B 0.9900 . ?
C39A C39A 1.546(13) 2_655 ?
C39A H39A 0.9900 . ?
C39A H39B 0.9900 . ?
K1B O2B 2.757(8) . ?
K1B O5 2.871(9) . ?
K1B O3B 2.929(8) . ?
K1B O4 2.941(7) . ?
K1B O1B 2.953(12) 2_655 ?
K1B N5 2.994(8) 2_655 ?
K1B N4 3.096(9) 2_655 ?
K1B N6 3.122(8) . ?
K1B N6 3.228(8) 2_655 ?
K1B K1B 3.816(13) 2_655 ?
O1B N4 1.157(7) . ?
O2B N6 1.114(6) . ?
O3B C34B 1.396(10) . ?
O3B C37B 1.402(10) . ?
C34B C35B 1.527(7) . ?
C34B H34C 0.9900 . ?
C34B H34D 0.9900 . ?
C35B C36B 1.529(7) . ?
C35B C37B 2.04(3) . ?
C35B H35C 0.9900 . ?
C35B H35D 0.9900 . ?
C36B C37B 1.524(7) . ?
C36B H36C 0.9900 . ?
C36B H36D 0.9900 . ?
C37B H37C 0.9900 . ?
C37B H37D 0.9900 . ?
C38B C39B 1.478(12) . ?
C38B O4 1.495(9) . ?
C38B H38C 0.9900 . ?
C38B H38D 0.9900 . ?
C39B C39B 1.532(10) 2_655 ?
C39B H39C 0.9900 . ?
C39B H39D 0.9900 . ?
N1 C1 1.347(3) . ?
N1 C3 1.405(3) . ?
N1 C10 1.454(3) . ?
N2 C1 1.352(3) . ?
N2 C2 1.394(3) . ?
N2 C22 1.449(3) . ?
N3 N4 1.282(4) . ?
N3 C2 1.383(3) . ?
N5 N6 1.286(3) . ?
N5 C3 1.387(3) . ?
C1 C4 1.468(3) . ?
C2 C3 1.375(3) . ?
C4 C5 1.393(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.397(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.395(4) . ?
C10 C15 1.400(4) . ?
C11 C12 1.399(4) . ?
C11 C16 1.516(4) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C15 C19 1.524(4) . ?
C16 C17 1.531(4) . ?
C16 C18 1.534(4) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.527(6) . ?
C19 C21 1.537(5) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.392(4) . ?
C22 C27 1.401(4) . ?
C23 C24 1.395(4) . ?
C23 C28 1.520(4) . ?
C24 C25 1.379(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.392(4) . ?
C26 H26 0.9500 . ?
C27 C31 1.513(4) . ?
C28 C30 1.529(4) . ?
C28 C29 1.534(4) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.502(5) . ?
C31 C33 1.516(5) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
O2A K1A N5 119.60(11) . 2_655 ?
O2A K1A O2A 75.70(10) . 2_655 ?
N5 K1A O2A 44.29(8) 2_655 2_655 ?
O2A K1A O5 109.97(12) . . ?
N5 K1A O5 130.42(12) 2_655 . ?
O2A K1A O5 172.46(13) 2_655 . ?
O2A K1A N4 156.18(14) . 2_655 ?
N5 K1A N4 64.38(8) 2_655 2_655 ?
O2A K1A N4 106.82(10) 2_655 2_655 ?
O5 K1A N4 70.14(12) . 2_655 ?
O2A K1A O3A 117.98(17) . . ?
N5 K1A O3A 80.85(14) 2_655 . ?
O2A K1A O3A 96.03(16) 2_655 . ?
O5 K1A O3A 77.00(16) . . ?
N4 K1A O3A 85.61(16) 2_655 . ?
O2A K1A O4 76.08(8) . . ?
N5 K1A O4 80.57(7) 2_655 . ?
O2A K1A O4 73.89(9) 2_655 . ?
O5 K1A O4 111.91(13) . . ?
N4 K1A O4 81.87(11) 2_655 . ?
O3A K1A O4 160.76(14) . . ?
O2A K1A N6 95.66(10) . 2_655 ?
N5 K1A N6 24.45(7) 2_655 2_655 ?
O2A K1A N6 22.95(7) 2_655 2_655 ?
O5 K1A N6 153.65(12) . 2_655 ?
N4 K1A N6 83.98(9) 2_655 2_655 ?
O3A K1A N6 96.71(14) . 2_655 ?
O4 K1A N6 67.55(7) . 2_655 ?
O2A K1A O1A 147.43(12) . 2_655 ?
N5 K1A O1A 85.56(8) 2_655 2_655 ?
O2A K1A O1A 128.47(10) 2_655 2_655 ?
O5 K1A O1A 48.71(11) . 2_655 ?
N4 K1A O1A 21.65(7) 2_655 2_655 ?
O3A K1A O1A 84.18(16) . 2_655 ?
O4 K1A O1A 89.41(11) . 2_655 ?
N6 K1A O1A 105.61(9) 2_655 2_655 ?
O2A K1A N6 19.41(7) . . ?
N5 K1A N6 127.67(10) 2_655 . ?
O2A K1A N6 87.59(9) 2_655 . ?
O5 K1A N6 99.24(11) . . ?
N4 K1A N6 138.01(12) 2_655 . ?
O3A K1A N6 132.92(16) . . ?
O4 K1A N6 64.20(6) . . ?
N6 K1A N6 103.44(8) 2_655 . ?
O1A K1A N6 128.54(11) 2_655 . ?
O2A K1A K1A 45.18(7) . 2_655 ?
N5 K1A K1A 78.77(8) 2_655 2_655 ?
O2A K1A K1A 42.21(7) 2_655 2_655 ?
O5 K1A K1A 145.31(12) . 2_655 ?
N4 K1A K1A 121.55(9) 2_655 2_655 ?
O3A K1A K1A 132.74(15) . 2_655 ?
O4 K1A K1A 47.14(7) . 2_655 ?
N6 K1A K1A 54.56(7) 2_655 2_655 ?
O1A K1A K1A 135.44(7) 2_655 2_655 ?
N6 K1A K1A 48.92(6) . 2_655 ?
N4 O1A K1A 59.7(2) . 2_655 ?
N6 O2A K1A 112.9(2) . . ?
N6 O2A K1A 90.71(18) . 2_655 ?
K1A O2A K1A 92.62(11) . 2_655 ?
C34A O3A C37A 109.4(7) . . ?
C34A O3A K1A 119.5(5) . . ?
C37A O3A K1A 114.0(5) . . ?
O3A C34A C35A 104.8(7) . . ?
O3A C34A H34A 110.8 . . ?
C35A C34A H34A 110.8 . . ?
O3A C34A H34B 110.8 . . ?
C35A C34A H34B 110.8 . . ?
H34A C34A H34B 108.9 . . ?
C34A C35A C36A 104.0(7) . . ?
C34A C35A H35A 110.9 . . ?
C36A C35A H35A 110.9 . . ?
C34A C35A H35B 110.9 . . ?
C36A C35A H35B 110.9 . . ?
H35A C35A H35B 109.0 . . ?
C35A C36A C37A 103.7(7) . . ?
C35A C36A H36A 111.0 . . ?
C37A C36A H36A 111.0 . . ?
C35A C36A H36B 111.0 . . ?
C37A C36A H36B 111.0 . . ?
H36A C36A H36B 109.0 . . ?
O3A C37A C36A 103.7(7) . . ?
O3A C37A H37A 111.0 . . ?
C36A C37A H37A 111.0 . . ?
O3A C37A H37B 111.0 . . ?
C36A C37A H37B 111.0 . . ?
H37A C37A H37B 109.0 . . ?
C39A C38A O4 106.6(6) . . ?
C39A C38A H38A 110.4 . . ?
O4 C38A H38A 110.4 . . ?
C39A C38A H38B 110.4 . . ?
O4 C38A H38B 110.4 . . ?
H38A C38A H38B 108.6 . . ?
C38A C39A C39A 98.9(5) . 2_655 ?
C38A C39A H39A 112.0 . . ?
C39A C39A H39A 112.0 2_655 . ?
C38A C39A H39B 112.0 . . ?
C39A C39A H39B 112.0 2_655 . ?
H39A C39A H39B 109.7 . . ?
O2B K1B O5 85.8(3) . . ?
O2B K1B O3B 128.6(4) . . ?
O5 K1B O3B 79.5(4) . . ?
O2B K1B O4 66.6(2) . . ?
O5 K1B O4 111.8(3) . . ?
O3B K1B O4 163.0(4) . . ?
O5 K1B O1B 74.4(3) . 2_655 ?
O4 K1B O1B 57.1(2) . 2_655 ?
O5 K1B N5 122.2(3) . 2_655 ?
O4 K1B N5 77.44(18) . 2_655 ?
O5 K1B N4 66.9(2) . 2_655 ?
O4 K1B N4 78.3(2) . 2_655 ?
N5 K1B N4 59.38(16) 2_655 2_655 ?
O2B K1B N6 20.68(14) . . ?
O5 K1B N6 104.7(3) . . ?
O3B K1B N6 123.5(4) . . ?
O4 K1B N6 67.41(15) . . ?
O1B K1B N6 117.7(3) 2_655 . ?
N5 K1B N6 129.2(2) 2_655 . ?
N4 K1B N6 138.6(3) 2_655 . ?
O2B K1B N6 120.8(3) . 2_655 ?
O5 K1B N6 144.6(3) . 2_655 ?
O3B K1B N6 97.3(4) . 2_655 ?
O4 K1B N6 65.97(15) . 2_655 ?
O1B K1B N6 76.1(2) 2_655 2_655 ?
N5 K1B N6 23.47(8) 2_655 2_655 ?
N4 K1B N6 78.49(19) 2_655 2_655 ?
N6 K1B N6 106.13(19) . 2_655 ?
O5 K1B K1B 154.3(3) . 2_655 ?
O4 K1B K1B 49.55(16) . 2_655 ?
N5 K1B K1B 75.1(2) 2_655 2_655 ?
N4 K1B K1B 117.0(2) 2_655 2_655 ?
N6 K1B K1B 54.35(18) . 2_655 ?
N6 K1B K1B 51.79(18) 2_655 2_655 ?
N4 O1B K1B 86.0(5) . 2_655 ?
N6 O2B K1B 98.4(4) . . ?
C34B O3B C37B 117.0(18) . . ?
C34B O3B K1B 61.3(9) . . ?
C37B O3B K1B 112.7(11) . . ?
O3B C34B C35B 84.5(17) . . ?
O3B C34B H34C 114.6 . . ?
C35B C34B H34C 114.6 . . ?
O3B C34B H34D 114.6 . . ?
C35B C34B H34D 114.6 . . ?
H34C C34B H34D 111.7 . . ?
C34B C35B C36B 123(2) . . ?
C34B C35B C37B 82.6(14) . . ?
C36B C35B C37B 48.0(9) . . ?
C34B C35B H35C 106.7 . . ?
C36B C35B H35C 106.7 . . ?
C37B C35B H35C 97.1 . . ?
C34B C35B H35D 106.7 . . ?
C36B C35B H35D 106.7 . . ?
C37B C35B H35D 150.3 . . ?
H35C C35B H35D 106.6 . . ?
C37B C36B C35B 83.8(18) . . ?
C37B C36B H36C 114.7 . . ?
C35B C36B H36C 114.7 . . ?
C37B C36B H36D 114.7 . . ?
C35B C36B H36D 114.7 . . ?
H36C C36B H36D 111.8 . . ?
O3B C37B C36B 114.0(18) . . ?
O3B C37B C35B 66.8(13) . . ?
C36B C37B C35B 48.2(9) . . ?
O3B C37B H37C 108.8 . . ?
C36B C37B H37C 108.8 . . ?
C35B C37B H37C 134.6 . . ?
O3B C37B H37D 108.8 . . ?
C36B C37B H37D 108.8 . . ?
C35B C37B H37D 116.6 . . ?
H37C C37B H37D 107.7 . . ?
C39B C38B O4 93.1(11) . . ?
C39B C38B H38C 113.1 . . ?
O4 C38B H38C 113.1 . . ?
C39B C38B H38D 113.1 . . ?
O4 C38B H38D 113.1 . . ?
H38C C38B H38D 110.5 . . ?
C38B C39B H39C 112.3 . . ?
C39B C39B H39C 112.3 2_655 . ?
C38B C39B H39D 112.3 . . ?
C39B C39B H39D 112.3 2_655 . ?
H39C C39B H39D 109.9 . . ?
C38A O4 C38A 104.0(6) . 2_655 ?
C38A O4 C38B 101.6(7) . 2_655 ?
C38B O4 C38B 114.8(13) 2_655 . ?
C38B O4 K1B 143.6(9) 2_655 . ?
C38B O4 K1B 90.9(7) . . ?
C38A O4 K1B 123.6(4) . 2_655 ?
C38A O4 K1B 112.6(4) 2_655 2_655 ?
C38A O4 K1A 115.1(4) . . ?
C38A O4 K1A 118.6(4) 2_655 . ?
C38A O4 K1A 118.6(4) . 2_655 ?
C38A O4 K1A 115.1(4) 2_655 2_655 ?
K1A O4 K1A 85.72(15) . 2_655 ?
C1 N1 C3 109.79(19) . . ?
C1 N1 C10 124.0(2) . . ?
C3 N1 C10 125.6(2) . . ?
C1 N2 C2 109.9(2) . . ?
C1 N2 C22 126.0(2) . . ?
C2 N2 C22 122.5(2) . . ?
N4 N3 C2 113.9(2) . . ?
O1B N4 N3 111.0(5) . . ?
O1A N4 N3 116.6(3) . . ?
O1A N4 K1A 98.6(2) . 2_655 ?
N3 N4 K1A 142.4(2) . 2_655 ?
O1A N4 K1B 96.9(3) . 2_655 ?
N3 N4 K1B 144.6(3) . 2_655 ?
N6 N5 C3 113.7(2) . . ?
N6 N5 K1A 91.55(18) . 2_655 ?
C3 N5 K1A 130.10(18) . 2_655 ?
N6 N5 K1B 88.5(2) . 2_655 ?
C3 N5 K1B 132.5(2) . 2_655 ?
O2B N6 N5 135.0(4) . . ?
O2A N6 N5 116.7(3) . . ?
O2A N6 K1A 66.34(18) . 2_655 ?
N5 N6 K1A 64.00(16) . 2_655 ?
O2B N6 K1B 60.9(4) . . ?
N5 N6 K1B 141.0(2) . . ?
O2A N6 K1B 62.8(2) . 2_655 ?
N5 N6 K1B 68.0(2) . 2_655 ?
O2A N6 K1A 47.69(18) . . ?
N5 N6 K1A 139.6(2) . . ?
K1A N6 K1A 76.53(8) 2_655 . ?
N1 C1 N2 107.2(2) . . ?
N1 C1 C4 127.3(2) . . ?
N2 C1 C4 125.4(2) . . ?
C3 C2 N3 135.8(2) . . ?
C3 C2 N2 106.8(2) . . ?
N3 C2 N2 117.2(2) . . ?
C2 C3 N5 126.6(2) . . ?
C2 C3 N1 106.3(2) . . ?
N5 C3 N1 126.7(2) . . ?
C5 C4 C9 119.2(2) . . ?
C5 C4 C1 122.0(2) . . ?
C9 C4 C1 118.7(2) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 120.5(3) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C11 C10 C15 123.4(2) . . ?
C11 C10 N1 119.0(2) . . ?
C15 C10 N1 117.5(2) . . ?
C10 C11 C12 116.5(3) . . ?
C10 C11 C16 123.6(2) . . ?
C12 C11 C16 119.9(2) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 117.1(3) . . ?
C14 C15 C19 119.9(3) . . ?
C10 C15 C19 123.0(2) . . ?
C11 C16 C17 109.6(2) . . ?
C11 C16 C18 111.2(2) . . ?
C17 C16 C18 111.9(2) . . ?
C11 C16 H16 108.0 . . ?
C17 C16 H16 108.0 . . ?
C18 C16 H16 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 C20 111.5(3) . . ?
C15 C19 C21 109.6(3) . . ?
C20 C19 C21 111.4(4) . . ?
C15 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C21 C19 H19 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 123.5(2) . . ?
C23 C22 N2 119.6(2) . . ?
C27 C22 N2 116.8(2) . . ?
C22 C23 C24 116.7(3) . . ?
C22 C23 C28 122.9(2) . . ?
C24 C23 C28 120.4(3) . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 117.0(3) . . ?
C26 C27 C31 120.4(3) . . ?
C22 C27 C31 122.5(2) . . ?
C23 C28 C30 112.1(3) . . ?
C23 C28 C29 110.9(2) . . ?
C30 C28 C29 109.5(2) . . ?
C23 C28 H28 108.1 . . ?
C30 C28 H28 108.1 . . ?
C29 C28 H28 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C27 112.1(3) . . ?
C32 C31 C33 112.8(4) . . ?
C27 C31 C33 111.0(3) . . ?
C32 C31 H31 106.8 . . ?
C27 C31 H31 106.8 . . ?
C33 C31 H31 106.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C37A O3A C34A C35A 38.2(9) . . . . ?
K1A O3A C34A C35A -95.8(7) . . . . ?
O3A C34A C35A C36A -22.0(9) . . . . ?
C34A C35A C36A C37A 0.0(9) . . . . ?
C34A O3A C37A C36A -37.9(9) . . . . ?
K1A O3A C37A C36A 98.8(6) . . . . ?
C35A C36A C37A O3A 21.1(9) . . . . ?
O4 C38A C39A C39A 40.5(10) . . . 2_655 ?
C37B O3B C34B C35B -31(2) . . . . ?
K1B O3B C34B C35B -133.2(16) . . . . ?
O3B C34B C35B C36B 46(3) . . . . ?
O3B C34B C35B C37B 18.4(12) . . . . ?
C34B C35B C36B C37B -39(3) . . . . ?
C34B O3B C37B C36B 15(3) . . . . ?
K1B O3B C37B C36B 83(2) . . . . ?
C34B O3B C37B C35B 24.5(16) . . . . ?
K1B O3B C37B C35B 92.8(12) . . . . ?
C35B C36B C37B O3B 12(2) . . . . ?
O4 C38B C39B C39B -50(2) . . . 2_655 ?
C39A C38A O4 C38A -16.3(4) . . . 2_655 ?
C39A C38A O4 K1A 115.1(6) . . . . ?
C39A C38A O4 K1A -145.6(6) . . . 2_655 ?
C39B C38B O4 C38B 19.9(9) . . . 2_655 ?
C39B C38B O4 K1B 173.2(12) . . . . ?
C39B C38B O4 K1B -111.0(14) . . . 2_655 ?
K1B O1B N4 N3 142.5(3) 2_655 . . . ?
K1A O1A N4 N3 -166.6(4) 2_655 . . . ?
C2 N3 N4 O1B -66.3(6) . . . . ?
C2 N3 N4 O1A -178.5(3) . . . . ?
C2 N3 N4 K1A 23.5(6) . . . 2_655 ?
C2 N3 N4 K1B 22.0(6) . . . 2_655 ?
K1B O2B N6 N5 -134.5(4) . . . . ?
K1B O2B N6 K1B -46.8(4) . . . 2_655 ?
K1A O2A N6 N5 134.0(2) . . . . ?
K1A O2A N6 N5 40.9(3) 2_655 . . . ?
K1A O2A N6 K1A 93.14(16) . . . 2_655 ?
K1A O2A N6 K1A -93.14(16) 2_655 . . . ?
C3 N5 N6 O2B -26.0(7) . . . . ?
K1B N5 N6 O2B 110.7(6) 2_655 . . . ?
C3 N5 N6 O2A -177.5(3) . . . . ?
K1A N5 N6 O2A -41.8(3) 2_655 . . . ?
C3 N5 N6 K1A -135.7(3) . . . 2_655 ?
C3 N5 N6 K1B -124.1(4) . . . . ?
K1B N5 N6 K1B 12.5(3) 2_655 . . . ?
C3 N5 N6 K1B -136.7(3) . . . 2_655 ?
C3 N5 N6 K1A -122.4(3) . . . . ?
K1A N5 N6 K1A 13.3(3) 2_655 . . . ?
C3 N1 C1 N2 -0.3(3) . . . . ?
C10 N1 C1 N2 -172.1(2) . . . . ?
C3 N1 C1 C4 -175.7(2) . . . . ?
C10 N1 C1 C4 12.5(4) . . . . ?
C2 N2 C1 N1 0.9(3) . . . . ?
C22 N2 C1 N1 166.7(2) . . . . ?
C2 N2 C1 C4 176.4(2) . . . . ?
C22 N2 C1 C4 -17.8(4) . . . . ?
N4 N3 C2 C3 -22.8(5) . . . . ?
N4 N3 C2 N2 162.4(3) . . . . ?
C1 N2 C2 C3 -1.1(3) . . . . ?
C22 N2 C2 C3 -167.5(2) . . . . ?
C1 N2 C2 N3 175.1(2) . . . . ?
C22 N2 C2 N3 8.7(4) . . . . ?
N3 C2 C3 N5 -0.6(5) . . . . ?
N2 C2 C3 N5 174.6(2) . . . . ?
N3 C2 C3 N1 -174.3(3) . . . . ?
N2 C2 C3 N1 0.9(3) . . . . ?
N6 N5 C3 C2 139.2(3) . . . . ?
K1A N5 C3 C2 25.0(4) 2_655 . . . ?
K1B N5 C3 C2 27.7(4) 2_655 . . . ?
N6 N5 C3 N1 -48.4(4) . . . . ?
K1A N5 C3 N1 -162.52(19) 2_655 . . . ?
K1B N5 C3 N1 -159.8(2) 2_655 . . . ?
C1 N1 C3 C2 -0.4(3) . . . . ?
C10 N1 C3 C2 171.3(2) . . . . ?
C1 N1 C3 N5 -174.1(2) . . . . ?
C10 N1 C3 N5 -2.4(4) . . . . ?
N1 C1 C4 C5 -43.5(4) . . . . ?
N2 C1 C4 C5 141.9(3) . . . . ?
N1 C1 C4 C9 134.4(3) . . . . ?
N2 C1 C4 C9 -40.3(4) . . . . ?
C9 C4 C5 C6 -0.3(4) . . . . ?
C1 C4 C5 C6 177.5(2) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C5 C4 C9 C8 -0.2(4) . . . . ?
C1 C4 C9 C8 -178.2(2) . . . . ?
C1 N1 C10 C11 -78.6(3) . . . . ?
C3 N1 C10 C11 110.8(3) . . . . ?
C1 N1 C10 C15 98.0(3) . . . . ?
C3 N1 C10 C15 -72.6(3) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
N1 C10 C11 C12 176.8(2) . . . . ?
C15 C10 C11 C16 179.5(2) . . . . ?
N1 C10 C11 C16 -4.1(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C16 C11 C12 C13 -179.3(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C13 C14 C15 C19 -179.7(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
N1 C10 C15 C14 -176.8(2) . . . . ?
C11 C10 C15 C19 179.4(3) . . . . ?
N1 C10 C15 C19 3.0(4) . . . . ?
C10 C11 C16 C17 -113.3(3) . . . . ?
C12 C11 C16 C17 65.8(3) . . . . ?
C10 C11 C16 C18 122.5(3) . . . . ?
C12 C11 C16 C18 -58.4(3) . . . . ?
C14 C15 C19 C20 62.7(4) . . . . ?
C10 C15 C19 C20 -117.0(3) . . . . ?
C14 C15 C19 C21 -61.1(4) . . . . ?
C10 C15 C19 C21 119.2(4) . . . . ?
C1 N2 C22 C23 110.5(3) . . . . ?
C2 N2 C22 C23 -85.3(3) . . . . ?
C1 N2 C22 C27 -72.6(3) . . . . ?
C2 N2 C22 C27 91.5(3) . . . . ?
C27 C22 C23 C24 1.1(4) . . . . ?
N2 C22 C23 C24 177.7(2) . . . . ?
C27 C22 C23 C28 -177.6(2) . . . . ?
N2 C22 C23 C28 -1.0(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C28 C23 C24 C25 178.6(3) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C27 -0.9(4) . . . . ?
C25 C26 C27 C22 1.8(4) . . . . ?
C25 C26 C27 C31 -175.7(3) . . . . ?
C23 C22 C27 C26 -1.9(4) . . . . ?
N2 C22 C27 C26 -178.6(2) . . . . ?
C23 C22 C27 C31 175.5(3) . . . . ?
N2 C22 C27 C31 -1.2(4) . . . . ?
C22 C23 C28 C30 -132.5(3) . . . . ?
C24 C23 C28 C30 48.9(3) . . . . ?
C22 C23 C28 C29 104.9(3) . . . . ?
C24 C23 C28 C29 -73.7(3) . . . . ?
C26 C27 C31 C32 -52.5(4) . . . . ?
C22 C27 C31 C32 130.2(4) . . . . ?
C26 C27 C31 C33 74.8(4) . . . . ?
C22 C27 C31 C33 -102.5(4) . . . . ?

_refine_diff_density_max         1.522
_refine_diff_density_min         -1.725
_refine_diff_density_rms         0.075




####################################################################### 
# 
# 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 1532917'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        6_LE-5-55
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H47 N4 O, Br'
_chemical_formula_sum            'C40 H47 Br N4 O'
_chemical_formula_weight         679.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   14.5259(3)
_cell_length_b                   19.9419(3)
_cell_length_c                   29.1694(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.0551(18)
_cell_angle_gamma                90
_cell_volume                     8292.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    15694
_cell_measurement_theta_min      3.7970
_cell_measurement_theta_max      75.6570

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_F_000             2864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.498
_exptl_crystal_size_min          0.347
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_T_max  0.685
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -2 -6 0.2062
8 -8 -4 0.1996
7 9 -3 0.2269
6 -6 -14 0.2078
6 -7 -13 0.2088
-7 4 14 0.2419
5 -6 11 0.1889
-5 6 -11 0.2539
9 1 -2 0.2174
-9 -3 5 0.2068
-8 -5 8 0.2261
-2 -8 15 0.2652
-7 8 8 0.2860
-2 13 3 0.3474
6 -10 -7 0.2360
-1 -1 19 0.1743
7 3 10 0.2192
8 4 6 0.2203
4 3 -18 0.1827
0 1 -19 0.2081
-4 5 -13 0.2462
3 7 -15 0.2127
-7 8 -3 0.2844
-9 3 2 0.2674
6 8 -10 0.1837
4 10 -10 0.2203
-5 10 -5 0.2989
8 6 1 0.2233
6 5 10 0.2362
0 2 19 0.2098
-7 -3 15 0.1695
-6 -3 15 0.1626
-1 -2 -18 0.2282
9 2 4 0.2156
6 0 12 0.1910
0 -4 18 0.1509
7 -9 2 0.2140
-3 -11 9 0.3418
3 -8 -15 0.2363
5 10 4 0.2695
-4 6 16 0.2690
-8 0 13 0.2057
3 6 15 0.2609
1 5 16 0.2539
-6 7 -7 0.2597
2 12 2 0.3075
-4 11 9 0.3241
-2 -3 18 0.1540
-7 -2 15 0.1662
4 -3 14 0.1789
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  33.00   1.00    4.00    --  -40.91  38.00  60.00   98
  2  ω     20.00 106.00   1.00    4.00    --   40.91  38.00 150.00   86
  3  ω     39.00  83.00   1.00   16.00    --  111.85 -45.00 120.00   44
  4  ω     43.00  83.00   1.00   16.00    --  111.85 -94.00  30.00   40
  5  ω     76.00 121.00   1.00   16.00    --  111.85-125.00 120.00   45
  6  ω     54.00  82.00   1.00    4.00    --   40.91-125.00  60.00   28
  7  ω     30.00 108.00   1.00   16.00    --  111.85 -94.00 -60.00   78
  8  ω     48.00 109.00   1.00   16.00    --  111.85 -94.00-150.00   61
  9  ω     45.00  95.00   1.00    4.00    --   40.91-125.00-120.00   50
 10  ω     42.00 108.00   1.00   16.00    --  111.85-125.00-180.00   66
 11  ω     40.00 138.00   1.00   16.00    --  111.85 -45.00-120.00   98
 12  ω    148.00 178.00   1.00   16.00    --  111.85  15.00 -90.00   30
 13  ω    128.00 167.00   1.00   16.00    --  111.85 103.00   9.00   39
 14  ω    113.00 139.00   1.00   16.00    --  111.85 125.00 -90.00   26
 15  ω    102.00 178.00   1.00   16.00    --  111.85  30.00 -30.00   76
 16  ω     85.00 178.00   1.00   16.00    --  111.85  30.00  60.00   93
 17  ω     64.00 105.00   1.00   16.00    --  111.85  15.00 -90.00   41
 18  ω     45.00 137.00   1.00   16.00    --  111.85 -45.00   0.00   92
 19  ω    -88.00 -21.00   1.00    4.00    --  -40.91 -38.00 150.00   67
 20  ω   -109.00 -16.00   1.00    4.00    --  -40.91 -38.00-120.00   93
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            29275
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         75.948
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8514
_reflns_number_gt                8030
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+10.9112P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8514
_refine_ls_number_parameters     461
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Br1 Br 0.500000 0.60692(2) 0.250000 0.03567(9) Uani 1 2 d S T P . .
Br2 Br 0.500000 0.96551(2) 0.250000 0.04587(10) Uani 1 2 d S T P . .
N1 N 0.72663(10) 0.75147(7) 0.30166(6) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.72462(10) 0.80456(7) 0.36641(5) 0.0297(3) Uani 1 1 d . . . . .
N3A N 0.6098(7) 0.7520(5) 0.4008(2) 0.0347(13) Uani 0.573(5) 1 d D U P A 1
N4A N 0.5476(2) 0.70862(17) 0.40373(13) 0.0383(9) Uani 0.573(5) 1 d D U P A 1
O1A O 0.5291(2) 0.66721(15) 0.36432(11) 0.0374(7) Uani 0.573(5) 1 d D U P A 1
C34A C 0.4663(3) 0.61343(18) 0.37036(17) 0.0438(10) Uani 0.573(5) 1 d D U P A 1
H34A H 0.433082 0.598391 0.339216 0.053 Uiso 0.573(5) 1 calc R U P A 1
H34B H 0.418696 0.630738 0.387488 0.053 Uiso 0.573(5) 1 calc R U P A 1
N3B N 0.5970(9) 0.7418(6) 0.3944(4) 0.0356(17) Uani 0.427(5) 1 d D U P A 2
N4B N 0.5534(4) 0.6892(3) 0.3785(2) 0.0408(11) Uani 0.427(5) 1 d D U P A 2
O1B O 0.4934(3) 0.67562(18) 0.40879(13) 0.0502(11) Uani 0.427(5) 1 d D U P A 2
C34B C 0.4481(4) 0.6135(2) 0.3913(3) 0.0563(17) Uani 0.427(5) 1 d D U P A 2
H34C H 0.420128 0.619145 0.357805 0.068 Uiso 0.427(5) 1 calc R U P A 2
H34D H 0.396552 0.604077 0.408151 0.068 Uiso 0.427(5) 1 calc R U P A 2
C1 C 0.76771(12) 0.80136(8) 0.32979(6) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.65513(12) 0.75498(9) 0.36133(7) 0.0315(4) Uani 1 1 d D . . . .
C3 C 0.65615(12) 0.72296(8) 0.32039(7) 0.0332(4) Uani 1 1 d . . . . .
H3 H 0.615819 0.687579 0.307210 0.040 Uiso 1 1 calc R U . . .
C4 C 0.84338(13) 0.84502(9) 0.32090(6) 0.0326(4) Uani 1 1 d . . . . .
C5 C 0.93175(16) 0.81994(12) 0.32110(8) 0.0480(5) Uani 1 1 d . . . . .
H5 H 0.944526 0.773726 0.327180 0.058 Uiso 1 1 calc R U . . .
C6 C 1.00221(18) 0.86248(15) 0.31236(10) 0.0596(6) Uani 1 1 d . . . . .
H6 H 1.063462 0.845399 0.312907 0.072 Uiso 1 1 calc R U . . .
C7 C 0.98361(18) 0.92912(13) 0.30294(7) 0.0523(6) Uani 1 1 d . . . . .
H7 H 1.032174 0.958027 0.297251 0.063 Uiso 1 1 calc R U . . .
C8 C 0.89567(19) 0.95396(12) 0.30173(8) 0.0528(6) Uani 1 1 d . . . . .
H8 H 0.883178 0.999952 0.294658 0.063 Uiso 1 1 calc R U . . .
C9 C 0.82422(17) 0.91263(10) 0.31074(8) 0.0453(5) Uani 1 1 d . . . . .
H9 H 0.763121 0.930127 0.310000 0.054 Uiso 1 1 calc R U . . .
C10 C 0.75908(13) 0.72712(9) 0.26063(7) 0.0335(4) Uani 1 1 d . . . . .
C11 C 0.73584(13) 0.76314(9) 0.21905(7) 0.0354(4) Uani 1 1 d . . . . .
C12 C 0.76940(16) 0.73796(11) 0.18080(8) 0.0437(5) Uani 1 1 d . . . . .
H12 H 0.755832 0.761048 0.151795 0.052 Uiso 1 1 calc R U . . .
C13 C 0.82242(17) 0.67957(12) 0.18453(8) 0.0495(5) Uani 1 1 d . . . . .
H13 H 0.844741 0.663274 0.158070 0.059 Uiso 1 1 calc R U . . .
C14 C 0.84311(16) 0.64490(11) 0.22620(8) 0.0463(5) Uani 1 1 d . . . . .
H14 H 0.879021 0.604842 0.227983 0.056 Uiso 1 1 calc R U . . .
C15 C 0.81204(14) 0.66789(10) 0.26560(7) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.67128(13) 0.82371(9) 0.21449(7) 0.0353(4) Uani 1 1 d . . . . .
H16 H 0.671661 0.841237 0.246645 0.042 Uiso 1 1 calc R U . . .
C17 C 0.70208(16) 0.88036(10) 0.18601(9) 0.0487(5) Uani 1 1 d . . . . .
H17A H 0.766512 0.893450 0.199714 0.073 Uiso 1 1 calc R U . . .
H17B H 0.660284 0.918904 0.186150 0.073 Uiso 1 1 calc R U . . .
H17C H 0.699306 0.865259 0.153804 0.073 Uiso 1 1 calc R U . . .
C18 C 0.57111(15) 0.80151(11) 0.19388(9) 0.0457(5) Uani 1 1 d . . . . .
H18A H 0.567365 0.787870 0.161296 0.069 Uiso 1 1 calc R U . . .
H18B H 0.527851 0.838845 0.195240 0.069 Uiso 1 1 calc R U . . .
H18C H 0.553940 0.763591 0.211893 0.069 Uiso 1 1 calc R U . . .
C19 C 0.83254(15) 0.62791(10) 0.31088(8) 0.0432(5) Uani 1 1 d . . . . .
H19 H 0.808861 0.653989 0.335515 0.052 Uiso 1 1 calc R U . . .
C20 C 0.93756(17) 0.61569(12) 0.32755(9) 0.0537(6) Uani 1 1 d . . . . .
H20A H 0.961210 0.587639 0.304762 0.081 Uiso 1 1 calc R U . . .
H20B H 0.948010 0.592884 0.357866 0.081 Uiso 1 1 calc R U . . .
H20C H 0.970764 0.658722 0.330706 0.081 Uiso 1 1 calc R U . . .
C21 C 0.77976(18) 0.56125(11) 0.30398(10) 0.0532(6) Uani 1 1 d . . . . .
H21A H 0.712457 0.569856 0.294075 0.080 Uiso 1 1 calc R U . . .
H21B H 0.790768 0.536258 0.333451 0.080 Uiso 1 1 calc R U . . .
H21C H 0.802217 0.534890 0.279975 0.080 Uiso 1 1 calc R U . . .
C22 C 0.75772(13) 0.84299(9) 0.40879(6) 0.0312(4) Uani 1 1 d . . . . .
C23 C 0.71603(14) 0.90413(10) 0.41495(7) 0.0354(4) Uani 1 1 d . . . . .
C24 C 0.74788(15) 0.93745(11) 0.45725(7) 0.0426(5) Uani 1 1 d . . . . .
H24 H 0.720899 0.979302 0.462907 0.051 Uiso 1 1 calc R U . . .
C25 C 0.81794(16) 0.91038(12) 0.49086(7) 0.0462(5) Uani 1 1 d . . . . .
H25 H 0.838197 0.933489 0.519500 0.055 Uiso 1 1 calc R U . . .
C26 C 0.85870(15) 0.85001(12) 0.48315(7) 0.0448(5) Uani 1 1 d . . . . .
H26 H 0.907177 0.832267 0.506545 0.054 Uiso 1 1 calc R U . . .
C27 C 0.83023(13) 0.81457(10) 0.44176(7) 0.0367(4) Uani 1 1 d . . . . .
C28 C 0.63767(15) 0.93469(10) 0.37897(8) 0.0430(5) Uani 1 1 d . . . . .
H28 H 0.632892 0.908704 0.349291 0.052 Uiso 1 1 calc R U . . .
C29 C 0.54397(17) 0.92898(14) 0.39498(10) 0.0607(7) Uani 1 1 d . . . . .
H29A H 0.530992 0.881755 0.400521 0.091 Uiso 1 1 calc R U . . .
H29B H 0.493960 0.947085 0.370762 0.091 Uiso 1 1 calc R U . . .
H29C H 0.546775 0.954447 0.423955 0.091 Uiso 1 1 calc R U . . .
C30 C 0.65820(19) 1.00800(11) 0.36868(9) 0.0540(6) Uani 1 1 d . . . . .
H30A H 0.653295 1.035762 0.395826 0.081 Uiso 1 1 calc R U . . .
H30B H 0.612711 1.023518 0.341488 0.081 Uiso 1 1 calc R U . . .
H30C H 0.721723 1.011578 0.362133 0.081 Uiso 1 1 calc R U . . .
C31 C 0.87568(15) 0.74772(11) 0.43418(8) 0.0451(5) Uani 1 1 d . . . . .
H31 H 0.853426 0.734744 0.400782 0.054 Uiso 1 1 calc R U . . .
C32 C 0.98236(17) 0.75354(15) 0.44232(12) 0.0661(7) Uani 1 1 d . . . . .
H32A H 0.999803 0.789624 0.422834 0.099 Uiso 1 1 calc R U . . .
H32B H 1.009011 0.711087 0.434051 0.099 Uiso 1 1 calc R U . . .
H32C H 1.006750 0.763627 0.475291 0.099 Uiso 1 1 calc R U . . .
C33 C 0.8437(2) 0.69314(15) 0.46436(13) 0.0776(9) Uani 1 1 d . . . . .
H33A H 0.866033 0.703766 0.497422 0.116 Uiso 1 1 calc R U . . .
H33B H 0.869545 0.649846 0.457159 0.116 Uiso 1 1 calc R U . . .
H33C H 0.775053 0.690773 0.457849 0.116 Uiso 1 1 calc R U . . .
C35 C 0.51530(19) 0.55307(11) 0.39680(10) 0.0600(7) Uani 1 1 d D . . . .
C36 C 0.5988(2) 0.53814(11) 0.38342(8) 0.0558(6) Uani 1 1 d . . . . .
H36 H 0.622530 0.567552 0.362854 0.067 Uiso 1 1 calc R U . . .
C37 C 0.6483(2) 0.48134(12) 0.39933(9) 0.0599(7) Uani 1 1 d . . . . .
H37 H 0.705523 0.471654 0.389517 0.072 Uiso 1 1 calc R U . . .
C38 C 0.6151(2) 0.43819(12) 0.42957(9) 0.0590(7) Uani 1 1 d . . . . .
H38 H 0.649776 0.399208 0.440853 0.071 Uiso 1 1 calc R U . . .
C39 C 0.5328(2) 0.45195(14) 0.44297(11) 0.0689(8) Uani 1 1 d . . . . .
H39 H 0.509421 0.422227 0.463499 0.083 Uiso 1 1 calc R U . . .
C40 C 0.4822(2) 0.50928(15) 0.42688(13) 0.0728(8) Uani 1 1 d . . . . .
H40 H 0.424678 0.518511 0.436547 0.087 Uiso 1 1 calc R 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
N1 C1 1.353(2) . ?
N1 C3 1.373(3) . ?
N1 C10 1.452(3) . ?
N2 C1 1.339(3) . ?
N2 C2 1.400(2) . ?
N2 C22 1.456(2) . ?
N3A N4A 1.266(5) . ?
N3A C2 1.433(5) . ?
N4A O1A 1.399(4) . ?
O1A C34A 1.440(4) . ?
C34A C35 1.530(4) . ?
C34A H34A 0.9900 . ?
C34A H34B 0.9900 . ?
N3B N4B 1.267(8) . ?
N3B C2 1.423(7) . ?
N4B O1B 1.381(7) . ?
O1B C34B 1.448(4) . ?
C34B C35 1.540(4) . ?
C34B H34C 0.9900 . ?
C34B H34D 0.9900 . ?
C1 C4 1.464(3) . ?
C2 C3 1.357(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 C9 1.397(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 C15 1.402(2) . ?
C11 C12 1.394(3) . ?
C11 C16 1.519(2) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C19 1.522(3) . ?
C16 C17 1.520(3) . ?
C16 C18 1.529(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.529(3) . ?
C19 C20 1.529(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.388(3) . ?
C22 C27 1.402(2) . ?
C23 C24 1.400(3) . ?
C23 C28 1.520(3) . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 C31 1.522(3) . ?
C28 C29 1.526(4) . ?
C28 C30 1.533(3) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.526(3) . ?
C31 C33 1.527(3) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C35 C36 1.376(4) . ?
C35 C40 1.387(4) . ?
C36 C37 1.374(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.356(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 109.83(16) . . ?
C1 N1 C10 124.79(16) . . ?
C3 N1 C10 125.06(15) . . ?
C1 N2 C2 108.63(15) . . ?
C1 N2 C22 125.01(15) . . ?
C2 N2 C22 125.15(16) . . ?
N4A N3A C2 121.7(5) . . ?
N3A N4A O1A 112.1(4) . . ?
N4A O1A C34A 111.4(3) . . ?
O1A C34A C35 113.8(3) . . ?
O1A C34A H34A 108.8 . . ?
C35 C34A H34A 108.8 . . ?
O1A C34A H34B 108.8 . . ?
C35 C34A H34B 108.8 . . ?
H34A C34A H34B 107.7 . . ?
N4B N3B C2 102.9(6) . . ?
N3B N4B O1B 105.1(6) . . ?
N4B O1B C34B 104.0(5) . . ?
O1B C34B C35 113.4(4) . . ?
O1B C34B H34C 108.9 . . ?
C35 C34B H34C 108.9 . . ?
O1B C34B H34D 108.9 . . ?
C35 C34B H34D 108.9 . . ?
H34C C34B H34D 107.7 . . ?
N2 C1 N1 107.42(16) . . ?
N2 C1 C4 126.48(16) . . ?
N1 C1 C4 126.08(18) . . ?
C3 C2 N2 107.23(17) . . ?
C3 C2 N3B 128.2(4) . . ?
N2 C2 N3B 124.6(4) . . ?
C3 C2 N3A 140.5(3) . . ?
N2 C2 N3A 112.1(3) . . ?
C2 C3 N1 106.87(15) . . ?
C2 C3 H3 126.6 . . ?
N1 C3 H3 126.6 . . ?
C5 C4 C9 119.95(19) . . ?
C5 C4 C1 120.95(18) . . ?
C9 C4 C1 119.07(18) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C11 C10 C15 124.09(19) . . ?
C11 C10 N1 118.83(16) . . ?
C15 C10 N1 117.08(17) . . ?
C12 C11 C10 116.57(18) . . ?
C12 C11 C16 121.40(18) . . ?
C10 C11 C16 121.88(18) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.81(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 116.81(19) . . ?
C14 C15 C19 120.26(18) . . ?
C10 C15 C19 122.89(19) . . ?
C11 C16 C17 113.42(18) . . ?
C11 C16 C18 109.21(15) . . ?
C17 C16 C18 110.97(17) . . ?
C11 C16 H16 107.7 . . ?
C17 C16 H16 107.7 . . ?
C18 C16 H16 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 C21 109.35(18) . . ?
C15 C19 C20 112.1(2) . . ?
C21 C19 C20 110.36(18) . . ?
C15 C19 H19 108.3 . . ?
C21 C19 H19 108.3 . . ?
C20 C19 H19 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 123.72(17) . . ?
C23 C22 N2 119.40(15) . . ?
C27 C22 N2 116.86(17) . . ?
C22 C23 C24 116.88(18) . . ?
C22 C23 C28 123.39(17) . . ?
C24 C23 C28 119.71(19) . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C26 C25 C24 120.43(19) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 121.29(19) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C22 116.67(19) . . ?
C26 C27 C31 120.37(18) . . ?
C22 C27 C31 122.95(18) . . ?
C23 C28 C29 110.7(2) . . ?
C23 C28 C30 111.69(17) . . ?
C29 C28 C30 110.5(2) . . ?
C23 C28 H28 108.0 . . ?
C29 C28 H28 108.0 . . ?
C30 C28 H28 108.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C31 C32 111.50(19) . . ?
C27 C31 C33 110.6(2) . . ?
C32 C31 C33 112.1(2) . . ?
C27 C31 H31 107.5 . . ?
C32 C31 H31 107.5 . . ?
C33 C31 H31 107.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C36 C35 C40 118.3(2) . . ?
C36 C35 C34A 112.2(3) . . ?
C40 C35 C34A 129.1(3) . . ?
C36 C35 C34B 135.6(4) . . ?
C40 C35 C34B 105.6(4) . . ?
C37 C36 C35 121.0(2) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 120.3(3) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 119.5(3) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C38 C39 C40 120.5(3) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C35 C40 C39 120.4(3) . . ?
C35 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3A N4A O1A -1.3(12) . . . . ?
N3A N4A O1A C34A 173.4(7) . . . . ?
N4A O1A C34A C35 -83.6(4) . . . . ?
C2 N3B N4B O1B -178.1(7) . . . . ?
N3B N4B O1B C34B -177.0(9) . . . . ?
N4B O1B C34B C35 67.6(6) . . . . ?
C2 N2 C1 N1 0.50(19) . . . . ?
C22 N2 C1 N1 168.45(15) . . . . ?
C2 N2 C1 C4 178.76(17) . . . . ?
C22 N2 C1 C4 -13.3(3) . . . . ?
C3 N1 C1 N2 0.48(19) . . . . ?
C10 N1 C1 N2 -173.31(15) . . . . ?
C3 N1 C1 C4 -177.80(16) . . . . ?
C10 N1 C1 C4 8.4(3) . . . . ?
C1 N2 C2 C3 -1.29(19) . . . . ?
C22 N2 C2 C3 -169.22(16) . . . . ?
C1 N2 C2 N3B 177.8(9) . . . . ?
C22 N2 C2 N3B 9.8(9) . . . . ?
C1 N2 C2 N3A 176.0(6) . . . . ?
C22 N2 C2 N3A 8.1(6) . . . . ?
N4B N3B C2 C3 6.0(16) . . . . ?
N4B N3B C2 N2 -172.8(6) . . . . ?
N4A N3A C2 C3 -1.2(16) . . . . ?
N4A N3A C2 N2 -177.1(8) . . . . ?
N2 C2 C3 N1 1.54(19) . . . . ?
N3B C2 C3 N1 -177.5(9) . . . . ?
N3A C2 C3 N1 -174.5(8) . . . . ?
C1 N1 C3 C2 -1.28(19) . . . . ?
C10 N1 C3 C2 172.49(16) . . . . ?
N2 C1 C4 C5 114.5(2) . . . . ?
N1 C1 C4 C5 -67.5(3) . . . . ?
N2 C1 C4 C9 -67.4(3) . . . . ?
N1 C1 C4 C9 110.6(2) . . . . ?
C9 C4 C5 C6 1.7(3) . . . . ?
C1 C4 C5 C6 179.7(2) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C5 C4 C9 C8 -1.1(3) . . . . ?
C1 C4 C9 C8 -179.21(19) . . . . ?
C1 N1 C10 C11 -80.3(2) . . . . ?
C3 N1 C10 C11 106.9(2) . . . . ?
C1 N1 C10 C15 100.0(2) . . . . ?
C3 N1 C10 C15 -72.8(2) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
N1 C10 C11 C12 179.45(17) . . . . ?
C15 C10 C11 C16 174.65(17) . . . . ?
N1 C10 C11 C16 -5.0(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C16 C11 C12 C13 -175.0(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C13 C14 C15 C19 177.9(2) . . . . ?
C11 C10 C15 C14 0.5(3) . . . . ?
N1 C10 C15 C14 -179.86(18) . . . . ?
C11 C10 C15 C19 -177.11(19) . . . . ?
N1 C10 C15 C19 2.5(3) . . . . ?
C12 C11 C16 C17 -44.2(3) . . . . ?
C10 C11 C16 C17 140.48(19) . . . . ?
C12 C11 C16 C18 80.1(2) . . . . ?
C10 C11 C16 C18 -95.2(2) . . . . ?
C14 C15 C19 C21 -66.2(3) . . . . ?
C10 C15 C19 C21 111.3(2) . . . . ?
C14 C15 C19 C20 56.5(3) . . . . ?
C10 C15 C19 C20 -126.0(2) . . . . ?
C1 N2 C22 C23 101.8(2) . . . . ?
C2 N2 C22 C23 -92.2(2) . . . . ?
C1 N2 C22 C27 -79.3(2) . . . . ?
C2 N2 C22 C27 86.7(2) . . . . ?
C27 C22 C23 C24 -1.6(3) . . . . ?
N2 C22 C23 C24 177.24(18) . . . . ?
C27 C22 C23 C28 179.81(19) . . . . ?
N2 C22 C23 C28 -1.3(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C28 C23 C24 C25 179.0(2) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C26 C27 C22 -0.7(3) . . . . ?
C25 C26 C27 C31 -179.5(2) . . . . ?
C23 C22 C27 C26 1.8(3) . . . . ?
N2 C22 C27 C26 -177.13(17) . . . . ?
C23 C22 C27 C31 -179.43(19) . . . . ?
N2 C22 C27 C31 1.7(3) . . . . ?
C22 C23 C28 C29 106.1(2) . . . . ?
C24 C23 C28 C29 -72.4(2) . . . . ?
C22 C23 C28 C30 -130.4(2) . . . . ?
C24 C23 C28 C30 51.1(3) . . . . ?
C26 C27 C31 C32 -53.0(3) . . . . ?
C22 C27 C31 C32 128.2(2) . . . . ?
C26 C27 C31 C33 72.5(3) . . . . ?
C22 C27 C31 C33 -106.3(3) . . . . ?
O1A C34A C35 C36 -41.1(5) . . . . ?
O1A C34A C35 C40 147.0(3) . . . . ?
O1B C34B C35 C36 -55.4(7) . . . . ?
O1B C34B C35 C40 116.7(5) . . . . ?
C40 C35 C36 C37 0.0(4) . . . . ?
C34A C35 C36 C37 -172.8(3) . . . . ?
C34B C35 C36 C37 171.4(4) . . . . ?
C35 C36 C37 C38 -0.5(4) . . . . ?
C36 C37 C38 C39 0.8(4) . . . . ?
C37 C38 C39 C40 -0.6(4) . . . . ?
C36 C35 C40 C39 0.1(4) . . . . ?
C34A C35 C40 C39 171.6(3) . . . . ?
C34B C35 C40 C39 -173.6(3) . . . . ?
C38 C39 C40 C35 0.2(5) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.049




_refine_special_details          ', SQUEEZE'
####################################################################### 
# 
# 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 1532912'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
# Beginning of Validation Reply Form
_vrf_PLAT029_shelx               
;
PROBLEM: diffrn_measured_fraction_theta_full value Low
RESPONSE: The value of the completeness could not be further improved,
since at the time of our data collection, the kappa-circle of the
goniometer had ceased to work. 
;

# End of Validation Reply Form
_chemical_name_systematic        1_LE-5-11
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H43 Li N6 O3, C4 H8 O'
_chemical_formula_sum            'C35 H51 Li N6 O4'
_chemical_formula_weight         626.75

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'
Li Li -0.0003 0.0001 '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                   15.33916(12)
_cell_length_b                   15.62771(7)
_cell_length_c                   15.99955(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.0396(9)
_cell_angle_gamma                90
_cell_volume                     3555.08(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18459
_cell_measurement_theta_min      1.5740
_cell_measurement_theta_max      28.8620

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7129
_diffrn_source                   synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source_type              'ESRF beamline SNBL'
_diffrn_source_details           'synchrotron radiation'
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  'Pilatus 2M Pixel Detector(Dectris)'
_diffrn_measurement_method       'Omega Scans'
_diffrn_reflns_number            131249
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.573
_diffrn_reflns_theta_max         24.793
_diffrn_reflns_theta_full        24.793
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             5741
_reflns_number_gt                5509
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+1.9855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5741
_refine_ls_number_parameters     463
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.058
_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
Li1 Li 0.52143(19) 0.46481(16) 0.92450(17) 0.0278(6) Uani 1 1 d . . . . .
O1 O 0.05124(7) 0.05973(7) 0.55328(7) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.44000(8) 0.39049(8) 0.83296(8) 0.0373(3) Uani 1 1 d D . . . .
O3 O 0.62520(8) 0.51690(8) 0.90376(9) 0.0397(3) Uani 1 1 d D . . . .
O4 O 0.71367(10) 0.31500(9) 0.68808(10) 0.0502(4) Uani 1 1 d D . . . .
N1 N 0.20801(9) 0.25068(8) 0.70104(8) 0.0222(3) Uani 1 1 d . . . . .
N2 N 0.31325(8) 0.21888(7) 0.64527(8) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.16839(9) 0.14393(8) 0.57891(8) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.11149(9) 0.10691(8) 0.61115(8) 0.0234(3) Uani 1 1 d . . . . .
N5A N 0.44370(11) 0.30821(10) 0.72260(11) 0.0276(4) Uani 0.828(3) 1 d D . P A 1
N6A N 0.48672(12) 0.36297(11) 0.78461(12) 0.0338(5) Uani 0.828(3) 1 d D . P A 1
N5B N 0.2871(5) 0.3488(5) 0.8163(5) 0.032(2) Uani 0.172(3) 1 d D . P A 2
N6B N 0.3656(4) 0.3918(6) 0.8582(6) 0.040(2) Uani 0.172(3) 1 d D . P A 2
C1 C 0.22609(10) 0.20011(9) 0.64102(9) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.35364(11) 0.28238(9) 0.71130(10) 0.0226(3) Uani 1 1 d D . . . .
H2 H 0.414593 0.306727 0.728136 0.027 Uiso 0.172(3) 1 calc R U P A 2
C3 C 0.28720(11) 0.30162(10) 0.74595(10) 0.0246(3) Uani 1 1 d D . . . .
H3 H 0.293397 0.342141 0.792095 0.030 Uiso 0.828(3) 1 calc R U P A 1
C4 C 0.11867(11) 0.26204(9) 0.71124(10) 0.0231(3) Uani 1 1 d . . . . .
C5 C 0.04638(11) 0.30554(9) 0.64314(10) 0.0240(3) Uani 1 1 d . . . . .
C6 C -0.03574(11) 0.32156(10) 0.65877(11) 0.0268(3) Uani 1 1 d . . . . .
H6 H -0.086180 0.350978 0.614336 0.032 Uiso 1 1 calc R U . . .
C7 C -0.04534(11) 0.29549(10) 0.73774(11) 0.0289(4) Uani 1 1 d . . . . .
H7 H -0.101510 0.307923 0.747313 0.035 Uiso 1 1 calc R U . . .
C8 C 0.02650(12) 0.25159(11) 0.80233(11) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.018852 0.233269 0.855783 0.036 Uiso 1 1 calc R U . . .
C9 C 0.11037(11) 0.23353(10) 0.79060(11) 0.0280(4) Uani 1 1 d . . . . .
C10 C 0.05625(12) 0.33502(10) 0.55607(11) 0.0277(4) Uani 1 1 d . . . . .
H10 H 0.100719 0.294606 0.544017 0.033 Uiso 1 1 calc R U . . .
C11 C 0.10091(13) 0.42419(11) 0.56817(12) 0.0363(4) Uani 1 1 d . . . . .
H11A H 0.059483 0.465637 0.580779 0.054 Uiso 1 1 calc R U . . .
H11B H 0.109895 0.440722 0.512860 0.054 Uiso 1 1 calc R U . . .
H11C H 0.161919 0.423215 0.618610 0.054 Uiso 1 1 calc R U . . .
C12 C -0.03588(13) 0.33190(12) 0.47424(12) 0.0377(4) Uani 1 1 d . . . . .
H12A H -0.062937 0.274367 0.468476 0.056 Uiso 1 1 calc R U . . .
H12B H -0.023863 0.345750 0.419784 0.056 Uiso 1 1 calc R U . . .
H12C H -0.080065 0.373582 0.481852 0.056 Uiso 1 1 calc R U . . .
C14 C 0.18753(13) 0.18330(13) 0.86227(12) 0.0390(4) Uani 1 1 d . . . . .
H14 H 0.242182 0.179321 0.842777 0.047 Uiso 1 1 calc R U . . .
C15 C 0.15465(17) 0.09224(15) 0.86925(16) 0.0579(6) Uani 1 1 d . . . . .
H15A H 0.100733 0.094164 0.887960 0.087 Uiso 1 1 calc R U . . .
H15B H 0.206020 0.060104 0.913863 0.087 Uiso 1 1 calc R U . . .
H15C H 0.136119 0.064038 0.810413 0.087 Uiso 1 1 calc R U . . .
C16 C 0.22068(15) 0.23165(18) 0.95259(13) 0.0566(6) Uani 1 1 d . . . . .
H16A H 0.248610 0.286428 0.946124 0.085 Uiso 1 1 calc R U . . .
H16B H 0.267692 0.197230 0.999101 0.085 Uiso 1 1 calc R U . . .
H16C H 0.166846 0.242094 0.970093 0.085 Uiso 1 1 calc R U . . .
C17 C 0.35488(10) 0.18783(9) 0.58310(10) 0.0204(3) Uani 1 1 d . . . . .
C18 C 0.32950(11) 0.22934(9) 0.49958(10) 0.0234(3) Uani 1 1 d . . . . .
C19 C 0.37150(12) 0.19999(10) 0.44098(10) 0.0277(4) Uani 1 1 d . . . . .
H19 H 0.355182 0.225727 0.383309 0.033 Uiso 1 1 calc R U . . .
C20 C 0.43625(12) 0.13426(10) 0.46567(11) 0.0275(4) Uani 1 1 d . . . . .
H20 H 0.464773 0.115866 0.425339 0.033 Uiso 1 1 calc R U . . .
C21 C 0.46003(11) 0.09478(10) 0.54910(11) 0.0256(3) Uani 1 1 d . . . . .
H21 H 0.504844 0.049692 0.565187 0.031 Uiso 1 1 calc R U . . .
C22 C 0.41911(11) 0.12031(9) 0.60961(10) 0.0229(3) Uani 1 1 d . . . . .
C23 C 0.25742(12) 0.30113(10) 0.47052(11) 0.0287(4) Uani 1 1 d . . . . .
H23 H 0.241329 0.316899 0.523592 0.034 Uiso 1 1 calc R U . . .
C24 C 0.16742(13) 0.26956(12) 0.39583(12) 0.0377(4) Uani 1 1 d . . . . .
H24A H 0.181376 0.252971 0.343093 0.057 Uiso 1 1 calc R U . . .
H24B H 0.120442 0.315443 0.379043 0.057 Uiso 1 1 calc R U . . .
H24C H 0.142784 0.220027 0.417488 0.057 Uiso 1 1 calc R U . . .
C25 C 0.29548(15) 0.38144(11) 0.44089(14) 0.0422(5) Uani 1 1 d . . . . .
H25A H 0.352315 0.401007 0.490246 0.063 Uiso 1 1 calc R U . . .
H25B H 0.247741 0.426638 0.425391 0.063 Uiso 1 1 calc R U . . .
H25C H 0.310730 0.368029 0.388099 0.063 Uiso 1 1 calc R U . . .
C26 C 0.44026(12) 0.07369(11) 0.69856(11) 0.0312(4) Uani 1 1 d . . . . .
H26 H 0.428723 0.114317 0.741592 0.037 Uiso 1 1 calc R U . . .
C27 C 0.37244(14) -0.00209(14) 0.68402(15) 0.0509(6) Uani 1 1 d . . . . .
H27A H 0.307449 0.018669 0.658487 0.076 Uiso 1 1 calc R U . . .
H27B H 0.383711 -0.030199 0.741899 0.076 Uiso 1 1 calc R U . . .
H27C H 0.382880 -0.043108 0.642377 0.076 Uiso 1 1 calc R U . . .
C28 C 0.54184(12) 0.04273(11) 0.74109(11) 0.0328(4) Uani 1 1 d . . . . .
H28A H 0.551966 -0.003831 0.704696 0.049 Uiso 1 1 calc R U . . .
H28B H 0.554246 0.021971 0.802292 0.049 Uiso 1 1 calc R U . . .
H28C H 0.584546 0.090157 0.743594 0.049 Uiso 1 1 calc R U . . .
C29 C 0.60987(16) 0.59607(14) 0.85711(19) 0.0617(7) Uani 1 1 d D . . . .
H29A H 0.604922 0.642905 0.896764 0.074 Uiso 1 1 calc R U . . .
H29B H 0.550710 0.593921 0.803266 0.074 Uiso 1 1 calc R U . . .
C30 C 0.69158(15) 0.61133(14) 0.82959(17) 0.0541(6) Uani 1 1 d . . . . .
H30A H 0.711308 0.672069 0.837930 0.065 Uiso 1 1 calc R U . . .
H30B H 0.676218 0.595094 0.765835 0.065 Uiso 1 1 calc R U . . .
C31 C 0.76749(15) 0.55355(13) 0.89288(18) 0.0552(6) Uani 1 1 d D . . . .
H31A H 0.802615 0.582404 0.950904 0.066 Uiso 0.759(8) 1 calc R U P B 1
H31B H 0.812182 0.534654 0.865250 0.066 Uiso 0.759(8) 1 calc R U P B 1
H31C H 0.824395 0.586851 0.927956 0.066 Uiso 0.241(8) 1 calc R U P B 2
H31D H 0.784984 0.508172 0.858896 0.066 Uiso 0.241(8) 1 calc R U P B 2
C32A C 0.70936(17) 0.47868(16) 0.9053(2) 0.0318(9) Uani 0.759(8) 1 d D . P B 1
H32A H 0.696272 0.436656 0.855796 0.038 Uiso 0.759(8) 1 calc R U P B 1
H32B H 0.742600 0.449397 0.963516 0.038 Uiso 0.759(8) 1 calc R U P B 1
C32B C 0.7205(4) 0.5138(7) 0.9570(6) 0.048(3) Uani 0.241(8) 1 d D . P B 2
H32C H 0.741705 0.454157 0.973855 0.058 Uiso 0.241(8) 1 calc R U P B 2
H32D H 0.735093 0.548272 1.012527 0.058 Uiso 0.241(8) 1 calc R U P B 2
C33 C 0.62226(13) 0.27867(13) 0.64355(13) 0.0408(4) Uani 1 1 d D . . . .
H33A H 0.597017 0.257942 0.688466 0.049 Uiso 1 1 calc R U . . .
H33B H 0.625592 0.229737 0.605562 0.049 Uiso 1 1 calc R U . . .
C34 C 0.56057(15) 0.34677(15) 0.58675(15) 0.0518(5) Uani 1 1 d . . . . .
H34A H 0.495330 0.341035 0.584152 0.062 Uiso 1 1 calc R U . . .
H34B H 0.560037 0.345483 0.524697 0.062 Uiso 1 1 calc R U . . .
C35 C 0.60610(16) 0.42747(15) 0.6354(2) 0.0632(6) Uani 1 1 d D . . . .
H35A H 0.587510 0.439543 0.687155 0.076 Uiso 0.838(9) 1 calc R U P C 1
H35B H 0.590648 0.477435 0.594361 0.076 Uiso 0.838(9) 1 calc R U P C 1
H35C H 0.562843 0.458069 0.658005 0.076 Uiso 0.162(9) 1 calc R U P C 2
H35D H 0.622279 0.465990 0.594239 0.076 Uiso 0.162(9) 1 calc R U P C 2
C36A C 0.70922(18) 0.40394(15) 0.6662(3) 0.0498(9) Uani 0.838(9) 1 d D U P C 1
H36A H 0.733005 0.414208 0.617428 0.060 Uiso 0.838(9) 1 calc R U P C 1
H36B H 0.747130 0.438047 0.719590 0.060 Uiso 0.838(9) 1 calc R U P C 1
C36B C 0.6961(10) 0.3998(7) 0.7149(10) 0.060(4) Uani 0.162(9) 1 d D U P C 2
H36C H 0.749106 0.438898 0.721904 0.072 Uiso 0.162(9) 1 calc R U P C 2
H36D H 0.685321 0.397945 0.772134 0.072 Uiso 0.162(9) 1 calc R U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Li1 O2 1.919(3) . ?
Li1 O3 1.924(3) . ?
Li1 O1 1.966(3) 2_556 ?
Li1 O1 1.974(3) 4_666 ?
Li1 N6B 2.498(7) . ?
Li1 N6A 2.633(3) . ?
Li1 Li1 2.945(5) 3_667 ?
O1 N4 1.2701(16) . ?
O2 N6A 1.309(2) . ?
O2 N6B 1.347(5) . ?
O3 C32B 1.390(6) . ?
O3 C32A 1.414(2) . ?
O3 C29 1.418(2) . ?
O4 C36A 1.429(3) . ?
O4 C33 1.430(2) . ?
O4 C36B 1.449(8) . ?
N1 C1 1.3504(18) . ?
N1 C3 1.404(2) . ?
N1 C4 1.4505(19) . ?
N2 C1 1.3452(19) . ?
N2 C2 1.4119(19) . ?
N2 C17 1.4524(18) . ?
N3 N4 1.3041(17) . ?
N3 C1 1.3717(19) . ?
N5A N6A 1.289(2) . ?
N5A C2 1.384(2) . ?
N5B N6B 1.321(8) . ?
N5B C3 1.346(6) . ?
C2 C3 1.364(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C9 1.396(2) . ?
C4 C5 1.404(2) . ?
C5 C6 1.396(2) . ?
C5 C10 1.528(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9500 . ?
C9 C14 1.521(2) . ?
C10 C12 1.525(3) . ?
C10 C11 1.533(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.528(3) . ?
C14 C16 1.538(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.397(2) . ?
C17 C18 1.403(2) . ?
C18 C19 1.399(2) . ?
C18 C23 1.520(2) . ?
C19 C20 1.380(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(2) . ?
C21 H21 0.9500 . ?
C22 C26 1.521(2) . ?
C23 C24 1.529(3) . ?
C23 C25 1.532(2) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C28 1.526(2) . ?
C26 C27 1.535(3) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.495(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.520(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32A 1.529(3) . ?
C31 C32B 1.586(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 H31C 0.9900 . ?
C31 H31D 0.9900 . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?
C33 C34 1.486(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.509(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36A 1.515(3) . ?
C35 C36B 1.547(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 H35C 0.9900 . ?
C35 H35D 0.9900 . ?
C36A H36A 0.9900 . ?
C36A H36B 0.9900 . ?
C36B H36C 0.9900 . ?
C36B H36D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Li1 O3 117.91(14) . . ?
O2 Li1 O1 110.11(14) . 2_556 ?
O3 Li1 O1 105.89(13) . 2_556 ?
O2 Li1 O1 120.58(14) . 4_666 ?
O3 Li1 O1 112.31(14) . 4_666 ?
O1 Li1 O1 83.27(11) 2_556 4_666 ?
O2 Li1 N6B 32.26(15) . . ?
O3 Li1 N6B 147.4(2) . . ?
O1 Li1 N6B 84.5(2) 2_556 . ?
O1 Li1 N6B 99.5(2) 4_666 . ?
O2 Li1 N6A 28.24(6) . . ?
O3 Li1 N6A 91.47(11) . . ?
O1 Li1 N6A 131.47(13) 2_556 . ?
O1 Li1 N6A 131.59(13) 4_666 . ?
O2 Li1 Li1 124.79(17) . 3_667 ?
O3 Li1 Li1 115.93(16) . 3_667 ?
O1 Li1 Li1 41.73(7) 2_556 3_667 ?
O1 Li1 Li1 41.54(7) 4_666 3_667 ?
N6A Li1 Li1 152.51(16) . 3_667 ?
N4 O1 Li1 127.81(12) . 2_546 ?
N4 O1 Li1 133.96(12) . 4_565 ?
Li1 O1 Li1 96.73(11) 2_546 4_565 ?
N6A O2 Li1 107.83(13) . . ?
N6B O2 Li1 98.3(3) . . ?
C32B O3 C29 106.4(4) . . ?
C32A O3 C29 110.36(15) . . ?
C32B O3 Li1 128.8(3) . . ?
C32A O3 Li1 128.83(14) . . ?
C29 O3 Li1 118.37(14) . . ?
C36A O4 C33 108.43(16) . . ?
C33 O4 C36B 104.7(6) . . ?
C1 N1 C3 109.06(12) . . ?
C1 N1 C4 127.33(12) . . ?
C3 N1 C4 123.07(12) . . ?
C1 N2 C2 109.86(12) . . ?
C1 N2 C17 125.21(12) . . ?
C2 N2 C17 124.40(12) . . ?
N4 N3 C1 110.07(11) . . ?
O1 N4 N3 112.41(12) . . ?
N6A N5A C2 119.45(15) . . ?
N5A N6A O2 115.95(16) . . ?
N5A N6A Li1 159.67(14) . . ?
N6B N5B C3 114.7(6) . . ?
N5B N6B O2 123.6(6) . . ?
N5B N6B Li1 173.0(5) . . ?
O2 N6B Li1 49.5(2) . . ?
N2 C1 N1 107.57(12) . . ?
N2 C1 N3 122.35(12) . . ?
N1 C1 N3 129.85(13) . . ?
C3 C2 N5A 138.06(14) . . ?
C3 C2 N2 105.91(13) . . ?
N5A C2 N2 116.02(13) . . ?
C3 C2 H2 127.0 . . ?
N2 C2 H2 127.0 . . ?
N5B C3 C2 134.1(3) . . ?
N5B C3 N1 117.8(3) . . ?
C2 C3 N1 107.58(13) . . ?
C2 C3 H3 126.2 . . ?
N1 C3 H3 126.2 . . ?
C9 C4 C5 123.04(14) . . ?
C9 C4 N1 118.41(14) . . ?
C5 C4 N1 118.44(13) . . ?
C6 C5 C4 116.79(14) . . ?
C6 C5 C10 120.94(14) . . ?
C4 C5 C10 122.27(14) . . ?
C7 C6 C5 121.46(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 120.07(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.17(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 117.44(15) . . ?
C4 C9 C14 122.66(14) . . ?
C8 C9 C14 119.89(14) . . ?
C12 C10 C5 113.34(14) . . ?
C12 C10 C11 111.33(14) . . ?
C5 C10 C11 110.58(13) . . ?
C12 C10 H10 107.1 . . ?
C5 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C14 C15 110.55(16) . . ?
C9 C14 C16 110.13(16) . . ?
C15 C14 C16 112.99(17) . . ?
C9 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C16 C14 H14 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 123.42(13) . . ?
C22 C17 N2 119.06(12) . . ?
C18 C17 N2 117.50(13) . . ?
C19 C18 C17 116.99(14) . . ?
C19 C18 C23 120.12(13) . . ?
C17 C18 C23 122.86(13) . . ?
C20 C19 C18 121.01(14) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.47(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 121.03(14) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 117.06(14) . . ?
C21 C22 C26 121.24(14) . . ?
C17 C22 C26 121.63(13) . . ?
C18 C23 C24 109.90(13) . . ?
C18 C23 C25 112.41(14) . . ?
C24 C23 C25 111.07(14) . . ?
C18 C23 H23 107.8 . . ?
C24 C23 H23 107.8 . . ?
C25 C23 H23 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C28 113.11(13) . . ?
C22 C26 C27 109.46(14) . . ?
C28 C26 C27 110.08(14) . . ?
C22 C26 H26 108.0 . . ?
C28 C26 H26 108.0 . . ?
C27 C26 H26 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O3 C29 C30 107.59(16) . . ?
O3 C29 H29A 110.2 . . ?
C30 C29 H29A 110.2 . . ?
O3 C29 H29B 110.2 . . ?
C30 C29 H29B 110.2 . . ?
H29A C29 H29B 108.5 . . ?
C29 C30 C31 103.08(16) . . ?
C29 C30 H30A 111.1 . . ?
C31 C30 H30A 111.1 . . ?
C29 C30 H30B 111.1 . . ?
C31 C30 H30B 111.1 . . ?
H30A C30 H30B 109.1 . . ?
C30 C31 C32A 101.71(17) . . ?
C30 C31 C32B 104.1(3) . . ?
C30 C31 H31A 111.4 . . ?
C32A C31 H31A 111.4 . . ?
C30 C31 H31B 111.4 . . ?
C32A C31 H31B 111.4 . . ?
H31A C31 H31B 109.3 . . ?
C30 C31 H31C 110.9 . . ?
C32B C31 H31C 110.9 . . ?
C30 C31 H31D 110.9 . . ?
C32B C31 H31D 110.9 . . ?
H31C C31 H31D 109.0 . . ?
O3 C32A C31 104.34(17) . . ?
O3 C32A H32A 110.9 . . ?
C31 C32A H32A 110.9 . . ?
O3 C32A H32B 110.9 . . ?
C31 C32A H32B 110.9 . . ?
H32A C32A H32B 108.9 . . ?
O3 C32B C31 102.6(5) . . ?
O3 C32B H32C 111.2 . . ?
C31 C32B H32C 111.2 . . ?
O3 C32B H32D 111.2 . . ?
C31 C32B H32D 111.2 . . ?
H32C C32B H32D 109.2 . . ?
O4 C33 C34 107.49(16) . . ?
O4 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
O4 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
C33 C34 C35 102.59(18) . . ?
C33 C34 H34A 111.2 . . ?
C35 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
C35 C34 H34B 111.2 . . ?
H34A C34 H34B 109.2 . . ?
C34 C35 C36A 100.92(19) . . ?
C34 C35 C36B 106.7(4) . . ?
C34 C35 H35A 111.6 . . ?
C36A C35 H35A 111.6 . . ?
C34 C35 H35B 111.6 . . ?
C36A C35 H35B 111.6 . . ?
H35A C35 H35B 109.4 . . ?
C34 C35 H35C 110.4 . . ?
C36B C35 H35C 110.4 . . ?
C34 C35 H35D 110.4 . . ?
C36B C35 H35D 110.4 . . ?
H35C C35 H35D 108.6 . . ?
O4 C36A C35 105.29(19) . . ?
O4 C36A H36A 110.7 . . ?
C35 C36A H36A 110.7 . . ?
O4 C36A H36B 110.7 . . ?
C35 C36A H36B 110.7 . . ?
H36A C36A H36B 108.8 . . ?
O4 C36B C35 102.7(6) . . ?
O4 C36B H36C 111.2 . . ?
C35 C36B H36C 111.2 . . ?
O4 C36B H36D 111.2 . . ?
C35 C36B H36D 111.2 . . ?
H36C C36B H36D 109.1 . . ?

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
Li1 O1 N4 N3 158.90(14) 2_546 . . . ?
Li1 O1 N4 N3 -3.7(2) 4_565 . . . ?
C1 N3 N4 O1 174.36(11) . . . . ?
C2 N5A N6A O2 -0.2(3) . . . . ?
C2 N5A N6A Li1 7.1(5) . . . . ?
Li1 O2 N6A N5A 176.37(16) . . . . ?
C3 N5B N6B O2 0.9(13) . . . . ?
Li1 O2 N6B N5B -179.4(9) . . . . ?
C2 N2 C1 N1 1.15(16) . . . . ?
C17 N2 C1 N1 -170.81(12) . . . . ?
C2 N2 C1 N3 176.17(13) . . . . ?
C17 N2 C1 N3 4.2(2) . . . . ?
C3 N1 C1 N2 -1.31(16) . . . . ?
C4 N1 C1 N2 170.44(13) . . . . ?
C3 N1 C1 N3 -175.83(14) . . . . ?
C4 N1 C1 N3 -4.1(2) . . . . ?
N4 N3 C1 N2 150.86(13) . . . . ?
N4 N3 C1 N1 -35.3(2) . . . . ?
N6A N5A C2 C3 4.5(3) . . . . ?
N6A N5A C2 N2 -176.71(15) . . . . ?
C1 N2 C2 C3 -0.54(16) . . . . ?
C17 N2 C2 C3 171.50(13) . . . . ?
C1 N2 C2 N5A -179.73(13) . . . . ?
C17 N2 C2 N5A -7.7(2) . . . . ?
N6B N5B C3 C2 6.2(11) . . . . ?
N6B N5B C3 N1 176.8(6) . . . . ?
N2 C2 C3 N5B 171.0(5) . . . . ?
N5A C2 C3 N1 178.64(18) . . . . ?
N2 C2 C3 N1 -0.27(16) . . . . ?
C1 N1 C3 N5B -171.9(4) . . . . ?
C4 N1 C3 N5B 15.9(5) . . . . ?
C1 N1 C3 C2 0.99(17) . . . . ?
C4 N1 C3 C2 -171.19(13) . . . . ?
C1 N1 C4 C9 114.03(17) . . . . ?
C3 N1 C4 C9 -75.28(19) . . . . ?
C1 N1 C4 C5 -69.55(19) . . . . ?
C3 N1 C4 C5 101.14(17) . . . . ?
C9 C4 C5 C6 1.5(2) . . . . ?
N1 C4 C5 C6 -174.77(13) . . . . ?
C9 C4 C5 C10 -179.02(14) . . . . ?
N1 C4 C5 C10 4.7(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C10 C5 C6 C7 -179.67(14) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
N1 C4 C9 C8 174.69(14) . . . . ?
C5 C4 C9 C14 177.45(15) . . . . ?
N1 C4 C9 C14 -6.3(2) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
C7 C8 C9 C14 -178.71(16) . . . . ?
C6 C5 C10 C12 -34.1(2) . . . . ?
C4 C5 C10 C12 146.41(15) . . . . ?
C6 C5 C10 C11 91.72(18) . . . . ?
C4 C5 C10 C11 -87.77(17) . . . . ?
C4 C9 C14 C15 -113.93(18) . . . . ?
C8 C9 C14 C15 65.0(2) . . . . ?
C4 C9 C14 C16 120.51(18) . . . . ?
C8 C9 C14 C16 -60.5(2) . . . . ?
C1 N2 C17 C22 -101.72(17) . . . . ?
C2 N2 C17 C22 87.45(17) . . . . ?
C1 N2 C17 C18 79.75(18) . . . . ?
C2 N2 C17 C18 -91.08(17) . . . . ?
C22 C17 C18 C19 0.3(2) . . . . ?
N2 C17 C18 C19 178.75(13) . . . . ?
C22 C17 C18 C23 178.24(14) . . . . ?
N2 C17 C18 C23 -3.3(2) . . . . ?
C17 C18 C19 C20 -1.2(2) . . . . ?
C23 C18 C19 C20 -179.25(14) . . . . ?
C18 C19 C20 C21 1.0(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C17 -1.0(2) . . . . ?
C20 C21 C22 C26 176.14(15) . . . . ?
C18 C17 C22 C21 0.8(2) . . . . ?
N2 C17 C22 C21 -177.61(13) . . . . ?
C18 C17 C22 C26 -176.34(14) . . . . ?
N2 C17 C22 C26 5.2(2) . . . . ?
C19 C18 C23 C24 68.92(18) . . . . ?
C17 C18 C23 C24 -108.98(16) . . . . ?
C19 C18 C23 C25 -55.3(2) . . . . ?
C17 C18 C23 C25 126.76(16) . . . . ?
C21 C22 C26 C28 36.2(2) . . . . ?
C17 C22 C26 C28 -146.76(15) . . . . ?
C21 C22 C26 C27 -86.95(18) . . . . ?
C17 C22 C26 C27 90.10(18) . . . . ?
C32B O3 C29 C30 39.6(6) . . . . ?
C32A O3 C29 C30 -2.1(3) . . . . ?
Li1 O3 C29 C30 -165.95(18) . . . . ?
O3 C29 C30 C31 -20.2(3) . . . . ?
C29 C30 C31 C32A 32.9(3) . . . . ?
C29 C30 C31 C32B -3.5(5) . . . . ?
C29 O3 C32A C31 23.5(3) . . . . ?
Li1 O3 C32A C31 -174.78(18) . . . . ?
C30 C31 C32A O3 -34.8(3) . . . . ?
C29 O3 C32B C31 -39.9(7) . . . . ?
Li1 O3 C32B C31 169.3(2) . . . . ?
C30 C31 C32B O3 26.2(8) . . . . ?
C36A O4 C33 C34 4.0(2) . . . . ?
C36B O4 C33 C34 41.0(8) . . . . ?
O4 C33 C34 C35 -26.7(2) . . . . ?
C33 C34 C35 C36A 37.4(3) . . . . ?
C33 C34 C35 C36B 3.6(9) . . . . ?
C33 O4 C36A C35 20.4(3) . . . . ?
C34 C35 C36A O4 -36.0(3) . . . . ?
C33 O4 C36B C35 -36.4(13) . . . . ?
C34 C35 C36B O4 19.8(14) . . . . ?

_refine_diff_density_max         0.577
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.040



_chemical_properties_physical    ', Heat-sensitive'
