# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1021785'
_audit_update_record             
;
2014-08-29 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_audit_creation_date             2014-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        alkyne-phenyl
_chemical_formula_moiety         'O3, C40 H32 O8'
_chemical_formula_sum            'C25 H0 N24 O0.50'
_chemical_formula_weight         644.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.974(9)
_cell_length_b                   13.036(10)
_cell_length_c                   14.337(11)
_cell_angle_alpha                68.085(14)
_cell_angle_beta                 67.898(13)
_cell_angle_gamma                73.316(14)
_cell_volume                     1737(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.335
_cell_measurement_theta_min      2.176
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             644
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8493
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3750
_reflns_number_total             5986
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.23A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          2.714
_refine_ls_shift/su_mean         0.082
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1284P)²+0.6139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2373
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O7 O 0.6163(10) 0.0038(9) 0.0287(8) 0.191(5) Uiso 1 1 d . . .
O8 O 0.8693(2) 0.10079(18) 0.28027(18) 0.0529(6) Uani 1 1 d . . .
O9 O 1.1931(2) 0.37129(19) 0.19505(18) 0.0585(6) Uani 1 1 d . . .
O4 O 1.1317(2) -0.1968(2) 0.2633(3) 0.0891(10) Uani 1 1 d . . .
O5 O 1.2779(4) -0.1240(3) 0.2781(3) 0.1111(13) Uani 1 1 d . . .
O1 O 1.4063(3) 0.3920(3) 0.0944(3) 0.0867(9) Uani 1 1 d . . .
O6 O 0.8854(3) -0.0622(2) 0.2486(3) 0.0772(8) Uani 1 1 d . . .
O2 O 1.4566(4) 0.3512(4) -0.0997(3) 0.1348(17) Uani 1 1 d . . .
O3 O 1.2918(3) 0.3063(3) -0.1195(2) 0.0865(9) Uani 1 1 d . . .
C35 C 1.0667(3) 0.0797(2) 0.3045(2) 0.0453(7) Uani 1 1 d . . .
C39 C 1.2561(3) 0.3388(3) 0.0390(3) 0.0565(9) Uani 1 1 d . . .
C31 C 0.9494(3) 0.1501(3) 0.3015(2) 0.0454(7) Uani 1 1 d . . .
C38 C 1.1183(3) 0.3233(3) 0.0926(2) 0.0491(8) Uani 1 1 d . . .
C26 C 0.8905(3) 0.2605(2) 0.3184(2) 0.0440(7) Uani 1 1 d . . .
C36 C 1.0853(3) 0.3420(3) 0.1871(3) 0.0487(8) Uani 1 1 d . . .
C27 C 0.9635(3) 0.3445(3) 0.2760(2) 0.0453(7) Uani 1 1 d . . .
C30 C 0.7490(3) 0.2747(3) 0.3840(2) 0.0479(8) Uani 1 1 d . . .
C28 C 0.9294(3) 0.4426(3) 0.3156(3) 0.0465(8) Uani 1 1 d . . .
C34 C 1.0623(3) -0.0175(3) 0.2815(2) 0.0482(8) Uani 1 1 d . . .
C42 C 1.1667(3) -0.1172(3) 0.2773(3) 0.0527(8) Uani 1 1 d . . .
C33 C 0.9412(3) 0.0011(3) 0.2691(3) 0.0522(8) Uani 1 1 d . . .
C40 C 1.2925(3) 0.3677(3) 0.1051(3) 0.0604(10) Uani 1 1 d . . .
C29 C 0.8870(3) 0.4291(3) 0.4238(3) 0.0581(9) Uani 1 1 d . . .
H29 H 0.8736 0.3588 0.4718 0.070 Uiso 1 1 calc . . R
C37 C 1.0255(3) 0.2953(3) 0.0576(2) 0.0536(8) Uani 1 1 d . . .
C1 C 1.1735(3) 0.1004(3) 0.3301(3) 0.0539(8) Uani 1 1 d . . .
C2 C 0.6600(3) 0.3712(3) 0.3527(3) 0.0602(9) Uani 1 1 d . . .
H2 H 0.6893 0.4266 0.2900 0.072 Uiso 1 1 calc . . R
C3 C 1.3438(4) 0.3348(3) -0.0662(3) 0.0687(11) Uani 1 1 d . . .
C4 C 0.7020(3) 0.1925(3) 0.4753(3) 0.0607(9) Uani 1 1 d . . .
H4 H 0.7596 0.1266 0.4960 0.073 Uiso 1 1 calc . . R
C5 C 0.9021(4) 0.3644(3) 0.0584(3) 0.0659(10) Uani 1 1 d . . .
H5 H 0.8815 0.4293 0.0778 0.079 Uiso 1 1 calc . . R
C6 C 0.9487(3) 0.5492(3) 0.2462(3) 0.0567(9) Uani 1 1 d . . .
H6 H 0.9770 0.5605 0.1738 0.068 Uiso 1 1 calc . . R
C7 C 1.1476(5) 0.1208(3) 0.4256(3) 0.0739(11) Uani 1 1 d . . .
H7 H 1.0623 0.1208 0.4736 0.089 Uiso 1 1 calc . . R
C8 C 1.3019(4) 0.1022(3) 0.2599(4) 0.0721(11) Uani 1 1 d . . .
H8 H 1.3206 0.0893 0.1960 0.086 Uiso 1 1 calc . . R
C9 C 0.9263(4) 0.6375(3) 0.2841(3) 0.0675(10) Uani 1 1 d . . .
H9 H 0.9391 0.7082 0.2369 0.081 Uiso 1 1 calc . . R
C10 C 0.8853(4) 0.6233(3) 0.3905(4) 0.0700(11) Uani 1 1 d . . .
H10 H 0.8716 0.6837 0.4150 0.084 Uiso 1 1 calc . . R
C11 C 0.4851(4) 0.3019(4) 0.5064(4) 0.0811(13) Uani 1 1 d . . .
H11 H 0.3966 0.3113 0.5481 0.097 Uiso 1 1 calc . . R
C12 C 0.8648(4) 0.5201(4) 0.4599(3) 0.0687(11) Uani 1 1 d . . .
H12 H 0.8357 0.5105 0.5320 0.082 Uiso 1 1 calc . . R
C13 C 0.5704(4) 0.2068(4) 0.5367(3) 0.0769(12) Uani 1 1 d . . .
H13 H 0.5401 0.1511 0.5989 0.092 Uiso 1 1 calc . . R
C14 C 0.5287(4) 0.3848(4) 0.4142(4) 0.0765(12) Uani 1 1 d . . .
H14 H 0.4698 0.4497 0.3935 0.092 Uiso 1 1 calc . . R
C15 C 1.0532(5) 0.2001(3) 0.0263(3) 0.0750(12) Uani 1 1 d . . .
H15 H 1.1351 0.1527 0.0242 0.090 Uiso 1 1 calc . . R
C16 C 1.2309(4) -0.2967(3) 0.2575(4) 0.0873(14) Uani 1 1 d . . .
H16A H 1.3015 -0.2805 0.1922 0.131 Uiso 1 1 calc . . GR
H16B H 1.1904 -0.3548 0.2609 0.131 Uiso 1 1 calc . . GR
H16C H 1.2666 -0.3214 0.3154 0.131 Uiso 1 1 calc . . GR
C17 C 1.4125(5) 0.4303(5) 0.1739(5) 0.1052(18) Uani 1 1 d . . .
H17A H 1.5002 0.4463 0.1556 0.158 Uiso 1 1 calc . . GR
H17B H 1.3939 0.3731 0.2407 0.158 Uiso 1 1 calc . . GR
H17C H 1.3478 0.4972 0.1786 0.158 Uiso 1 1 calc . . GR
C18 C 0.7505(4) -0.0233(4) 0.2453(4) 0.0921(15) Uani 1 1 d . . .
H18A H 0.7445 0.0490 0.1936 0.138 Uiso 1 1 calc . . GR
H18B H 0.6928 -0.0174 0.3133 0.138 Uiso 1 1 calc . . GR
H18C H 0.7240 -0.0753 0.2268 0.138 Uiso 1 1 calc . . GR
C19 C 1.3737(7) 0.1407(5) 0.3790(7) 0.119(2) Uani 1 1 d . . .
H19 H 1.4413 0.1528 0.3959 0.143 Uiso 1 1 calc . . R
C20 C 0.8103(5) 0.3379(5) 0.0310(4) 0.0930(15) Uani 1 1 d . . .
H20 H 0.7282 0.3848 0.0326 0.112 Uiso 1 1 calc . . R
C21 C 1.3764(5) 0.2978(5) -0.2227(3) 0.0950(15) Uani 1 1 d . . .
H21A H 1.4104 0.3665 -0.2639 0.143 Uiso 1 1 calc . . GR
H21B H 1.3254 0.2843 -0.2574 0.143 Uiso 1 1 calc . . GR
H21C H 1.4495 0.2368 -0.2152 0.143 Uiso 1 1 calc . . GR
C22 C 1.4015(5) 0.1226(4) 0.2829(5) 0.1014(17) Uani 1 1 d . . .
H22 H 1.4867 0.1242 0.2348 0.122 Uiso 1 1 calc . . R
C23 C 0.9604(7) 0.1754(5) -0.0016(4) 0.1009(17) Uani 1 1 d . . .
H23 H 0.9804 0.1116 -0.0227 0.121 Uiso 1 1 calc . . R
C24 C 1.2483(8) 0.1410(4) 0.4487(5) 0.1059(19) Uani 1 1 d . . .
H24 H 1.2305 0.1548 0.5121 0.127 Uiso 1 1 calc . . R
C25 C 0.8378(7) 0.2442(7) 0.0015(4) 0.1092(19) Uani 1 1 d . . .
H25 H 0.7750 0.2265 -0.0165 0.131 Uiso 1 1 calc . . R
O10 O 0.5133(17) 0.0658(11) -0.0300(12) 0.370(7) Uiso 1 1 d . . .
O11 O 0.6019(8) 0.0490(7) 0.0099(6) 0.160(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 O10 1.52(2) . ?
O7 O11 0.552(12) . ?
O8 C31 1.397(4) . ?
O8 C33 1.345(4) . ?
O9 C36 1.397(4) . ?
O9 C40 1.347(4) . ?
O4 C42 1.306(4) . ?
O4 C16 1.445(4) . ?
O5 C42 1.202(4) . ?
O1 C40 1.315(4) . ?
O1 C17 1.434(5) . ?
O6 C33 1.323(4) . ?
O6 C18 1.432(5) . ?
O2 C3 1.199(5) . ?
O3 C3 1.307(5) . ?
O3 C21 1.446(5) . ?
C35 C31 1.355(4) . ?
C35 C34 1.441(4) . ?
C35 C1 1.469(5) . ?
C39 C38 1.451(5) . ?
C39 C40 1.355(5) . ?
C39 C3 1.463(5) . ?
C31 C26 1.468(4) . ?
C38 C36 1.361(5) . ?
C38 C37 1.468(5) . ?
C26 C27 1.360(4) . ?
C26 C30 1.483(4) . ?
C36 C27 1.461(4) . ?
C27 C28 1.485(4) . ?
C30 C2 1.393(5) . ?
C30 C4 1.374(5) . ?
C28 C29 1.398(5) . ?
C28 C6 1.394(5) . ?
C34 C42 1.469(4) . ?
C34 C33 1.349(5) . ?
C29 C12 1.391(5) . ?
C37 C5 1.393(5) . ?
C37 C15 1.389(5) . ?
C1 C7 1.400(5) . ?
C1 C8 1.390(5) . ?
C2 C14 1.378(5) . ?
C4 C13 1.381(5) . ?
C5 C20 1.374(6) . ?
C6 C9 1.374(5) . ?
C7 C24 1.383(7) . ?
C8 C22 1.370(6) . ?
C9 C10 1.372(6) . ?
C10 C12 1.362(6) . ?
C11 C13 1.357(6) . ?
C11 C14 1.378(6) . ?
C15 C23 1.375(7) . ?
C19 C22 1.391(9) . ?
C19 C24 1.362(8) . ?
C20 C25 1.356(8) . ?
C23 C25 1.381(8) . ?
O10 O10 1.66(2) 2_655 ?
O10 O11 1.235(15) . ?

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
O11 O7 O10 49.0(15) . . ?
C33 O8 C31 106.1(2) . . ?
C40 O9 C36 105.9(3) . . ?
C42 O4 C16 116.1(3) . . ?
C40 O1 C17 118.2(3) . . ?
C33 O6 C18 118.2(3) . . ?
C3 O3 C21 116.7(3) . . ?
C31 C35 C34 106.7(3) . . ?
C31 C35 C1 125.1(3) . . ?
C34 C35 C1 128.1(3) . . ?
C38 C39 C3 131.4(4) . . ?
C40 C39 C38 105.5(3) . . ?
C40 C39 C3 123.0(3) . . ?
O8 C31 C26 116.1(3) . . ?
C35 C31 O8 109.4(3) . . ?
C35 C31 C26 134.4(3) . . ?
C39 C38 C37 130.0(3) . . ?
C36 C38 C39 106.1(3) . . ?
C36 C38 C37 123.9(3) . . ?
C31 C26 C30 116.6(3) . . ?
C27 C26 C31 121.1(3) . . ?
C27 C26 C30 122.3(3) . . ?
O9 C36 C27 115.1(3) . . ?
C38 C36 O9 110.1(3) . . ?
C38 C36 C27 134.7(3) . . ?
C26 C27 C36 120.9(3) . . ?
C26 C27 C28 124.0(3) . . ?
C36 C27 C28 115.1(3) . . ?
C2 C30 C26 120.3(3) . . ?
C4 C30 C26 121.0(3) . . ?
C4 C30 C2 118.7(3) . . ?
C29 C28 C27 120.8(3) . . ?
C6 C28 C27 121.0(3) . . ?
C6 C28 C29 118.0(3) . . ?
C35 C34 C42 126.6(3) . . ?
C33 C34 C35 105.5(3) . . ?
C33 C34 C42 127.9(3) . . ?
O4 C42 C34 113.6(3) . . ?
O5 C42 O4 121.6(3) . . ?
O5 C42 C34 124.5(3) . . ?
O8 C33 C34 112.2(3) . . ?
O6 C33 O8 117.4(3) . . ?
O6 C33 C34 130.4(3) . . ?
O9 C40 C39 112.3(3) . . ?
O1 C40 O9 117.2(3) . . ?
O1 C40 C39 130.5(3) . . ?
C12 C29 C28 120.3(3) . . ?
C5 C37 C38 119.4(3) . . ?
C15 C37 C38 122.9(3) . . ?
C15 C37 C5 117.7(4) . . ?
C7 C1 C35 120.5(3) . . ?
C8 C1 C35 121.2(3) . . ?
C8 C1 C7 118.2(4) . . ?
C14 C2 C30 120.3(4) . . ?
O2 C3 O3 122.1(4) . . ?
O2 C3 C39 123.1(5) . . ?
O3 C3 C39 114.7(3) . . ?
C30 C4 C13 120.7(4) . . ?
C20 C5 C37 121.0(4) . . ?
C9 C6 C28 120.4(3) . . ?
C24 C7 C1 120.2(5) . . ?
C22 C8 C1 121.5(4) . . ?
C6 C9 C10 121.2(4) . . ?
C12 C10 C9 119.5(3) . . ?
C13 C11 C14 120.4(4) . . ?
C10 C12 C29 120.6(4) . . ?
C11 C13 C4 120.1(4) . . ?
C2 C14 C11 119.8(4) . . ?
C23 C15 C37 120.5(5) . . ?
C24 C19 C22 120.6(5) . . ?
C25 C20 C5 120.9(5) . . ?
C8 C22 C19 119.2(5) . . ?
C15 C23 C25 120.8(5) . . ?
C19 C24 C7 120.3(5) . . ?
C20 C25 C23 119.2(5) . . ?
O7 O10 O10 72.4(11) . 2_655 ?
O11 O10 O7 19.7(6) . . ?
O11 O10 O10 91.7(14) . 2_655 ?
O7 O11 O10 111.2(19) . . ?

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
O8 C31 C26 C27 -137.9(3) . . . . ?
O8 C31 C26 C30 42.4(4) . . . . ?
O9 C36 C27 C26 -136.2(3) . . . . ?
O9 C36 C27 C28 42.8(4) . . . . ?
C35 C31 C26 C27 44.5(5) . . . . ?
C35 C31 C26 C30 -135.3(4) . . . . ?
C35 C34 C42 O4 174.6(3) . . . . ?
C35 C34 C42 O5 -11.0(6) . . . . ?
C35 C34 C33 O8 0.9(4) . . . . ?
C35 C34 C33 O6 -178.9(3) . . . . ?
C35 C1 C7 C24 -179.5(3) . . . . ?
C35 C1 C8 C22 179.4(4) . . . . ?
C39 C38 C36 O9 1.6(3) . . . . ?
C39 C38 C36 C27 177.3(3) . . . . ?
C39 C38 C37 C5 -125.6(4) . . . . ?
C39 C38 C37 C15 56.5(5) . . . . ?
C31 O8 C33 O6 179.8(3) . . . . ?
C31 O8 C33 C34 0.0(4) . . . . ?
C31 C35 C34 C42 -179.2(3) . . . . ?
C31 C35 C34 C33 -1.5(3) . . . . ?
C31 C35 C1 C7 56.6(5) . . . . ?
C31 C35 C1 C8 -122.4(4) . . . . ?
C31 C26 C27 C36 19.6(5) . . . . ?
C31 C26 C27 C28 -159.2(3) . . . . ?
C31 C26 C30 C2 -135.5(3) . . . . ?
C31 C26 C30 C4 43.1(4) . . . . ?
C38 C39 C40 O9 0.5(4) . . . . ?
C38 C39 C40 O1 -179.3(4) . . . . ?
C38 C39 C3 O2 178.9(4) . . . . ?
C38 C39 C3 O3 -4.2(6) . . . . ?
C38 C36 C27 C26 48.3(5) . . . . ?
C38 C36 C27 C28 -132.8(4) . . . . ?
C38 C37 C5 C20 -176.9(3) . . . . ?
C38 C37 C15 C23 177.3(3) . . . . ?
C26 C27 C28 C29 42.8(5) . . . . ?
C26 C27 C28 C6 -142.3(3) . . . . ?
C26 C30 C2 C14 -179.4(3) . . . . ?
C26 C30 C4 C13 179.3(3) . . . . ?
C36 O9 C40 O1 -179.8(3) . . . . ?
C36 O9 C40 C39 0.5(4) . . . . ?
C36 C38 C37 C5 53.3(5) . . . . ?
C36 C38 C37 C15 -124.7(4) . . . . ?
C36 C27 C28 C29 -136.0(3) . . . . ?
C36 C27 C28 C6 38.8(4) . . . . ?
C27 C26 C30 C2 44.8(5) . . . . ?
C27 C26 C30 C4 -136.7(3) . . . . ?
C27 C28 C29 C12 175.2(3) . . . . ?
C27 C28 C6 C9 -175.1(3) . . . . ?
C30 C26 C27 C36 -160.7(3) . . . . ?
C30 C26 C27 C28 20.5(5) . . . . ?
C30 C2 C14 C11 -0.8(6) . . . . ?
C30 C4 C13 C11 1.1(6) . . . . ?
C28 C29 C12 C10 -0.7(6) . . . . ?
C28 C6 C9 C10 0.4(6) . . . . ?
C34 C35 C31 O8 1.5(3) . . . . ?
C34 C35 C31 C26 179.3(3) . . . . ?
C34 C35 C1 C7 -121.3(4) . . . . ?
C34 C35 C1 C8 59.7(5) . . . . ?
C42 C34 C33 O8 178.6(3) . . . . ?
C42 C34 C33 O6 -1.2(6) . . . . ?
C33 O8 C31 C35 -1.0(3) . . . . ?
C33 O8 C31 C26 -179.2(3) . . . . ?
C33 C34 C42 O4 -2.6(5) . . . . ?
C33 C34 C42 O5 171.8(4) . . . . ?
C40 O9 C36 C38 -1.3(4) . . . . ?
C40 O9 C36 C27 -177.9(3) . . . . ?
C40 C39 C38 C36 -1.2(4) . . . . ?
C40 C39 C38 C37 177.8(3) . . . . ?
C40 C39 C3 O2 3.8(6) . . . . ?
C40 C39 C3 O3 -179.3(4) . . . . ?
C29 C28 C6 C9 -0.1(5) . . . . ?
C37 C38 C36 O9 -177.5(3) . . . . ?
C37 C38 C36 C27 -1.8(6) . . . . ?
C37 C5 C20 C25 -0.6(6) . . . . ?
C37 C15 C23 C25 -0.3(7) . . . . ?
C1 C35 C31 O8 -176.8(3) . . . . ?
C1 C35 C31 C26 1.0(6) . . . . ?
C1 C35 C34 C42 -1.0(5) . . . . ?
C1 C35 C34 C33 176.7(3) . . . . ?
C1 C7 C24 C19 -0.3(7) . . . . ?
C1 C8 C22 C19 0.7(7) . . . . ?
C2 C30 C4 C13 -2.1(5) . . . . ?
C3 C39 C38 C36 -177.0(3) . . . . ?
C3 C39 C38 C37 2.0(6) . . . . ?
C3 C39 C40 O9 176.7(3) . . . . ?
C3 C39 C40 O1 -3.0(6) . . . . ?
C4 C30 C2 C14 2.0(5) . . . . ?
C5 C37 C15 C23 -0.7(5) . . . . ?
C5 C20 C25 C23 -0.5(7) . . . . ?
C6 C28 C29 C12 0.2(5) . . . . ?
C6 C9 C10 C12 -0.9(6) . . . . ?
C7 C1 C8 C22 0.4(6) . . . . ?
C8 C1 C7 C24 -0.6(5) . . . . ?
C9 C10 C12 C29 1.0(6) . . . . ?
C13 C11 C14 C2 -0.4(7) . . . . ?
C14 C11 C13 C4 0.2(7) . . . . ?
C15 C37 C5 C20 1.2(5) . . . . ?
C15 C23 C25 C20 0.9(7) . . . . ?
C16 O4 C42 O5 4.9(6) . . . . ?
C16 O4 C42 C34 179.4(3) . . . . ?
C17 O1 C40 O9 -5.6(6) . . . . ?
C17 O1 C40 C39 174.2(4) . . . . ?
C18 O6 C33 O8 -3.3(5) . . . . ?
C18 O6 C33 C34 176.5(4) . . . . ?
C21 O3 C3 O2 -1.2(7) . . . . ?
C21 O3 C3 C39 -178.1(4) . . . . ?
C22 C19 C24 C7 1.4(8) . . . . ?
C24 C19 C22 C8 -1.5(8) . . . . ?
O10 O10 O11 O7 12(2) 2_655 . . . ?
O11 O7 O10 O10 -168(2) . . . 2_655 ?

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1021786'
_audit_update_record             
;
2014-08-29 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_audit_creation_date             2014-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        alkyne-butyle
_chemical_formula_moiety         'C36 H40 O8'
_chemical_formula_sum            'C36 H40 O8'
_chemical_formula_weight         600.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.6210(11)
_cell_length_b                   21.744(3)
_cell_length_c                   18.379(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.954(3)
_cell_angle_gamma                90
_cell_volume                     3382.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    850
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.11
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8352
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.187
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1510
_reflns_number_total             2972
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.23A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1443
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5757(2) 0.68205(7) 0.32990(11) 0.0589(6) Uani 1 1 d . . . . .
O2 O 0.6392(2) 0.58568(8) 0.37396(13) 0.0806(7) Uani 1 1 d . . . . .
O3 O 0.3696(2) 0.52979(9) 0.40572(13) 0.0827(7) Uani 1 1 d . . . . .
O4 O 0.1498(3) 0.58483(9) 0.39413(13) 0.0824(7) Uani 1 1 d . . . . .
C1 C -0.0898(4) 0.79942(18) 0.4569(2) 0.1093(13) Uani 1 1 d . . . . .
H1A H -0.1015 0.7659 0.4894 0.164 Uiso 1 1 calc GR . . . .
H1B H -0.1885 0.8209 0.4437 0.164 Uiso 1 1 calc GR . . . .
H1C H -0.0103 0.8272 0.4816 0.164 Uiso 1 1 calc GR . . . .
C2 C -0.0415(3) 0.77489(13) 0.38800(17) 0.0704(9) Uani 1 1 d . . . . .
H2A H -0.0292 0.8091 0.3558 0.084 Uiso 1 1 calc R . . . .
H2B H -0.1255 0.7489 0.3619 0.084 Uiso 1 1 calc R . . . .
C3 C 0.1111(3) 0.73813(12) 0.40290(15) 0.0553(7) Uani 1 1 d . . . . .
H3A H 0.0985 0.7030 0.4338 0.066 Uiso 1 1 calc R . . . .
H3B H 0.1953 0.7636 0.4297 0.066 Uiso 1 1 calc R . . . .
C4 C 0.1563(3) 0.71584(12) 0.33127(14) 0.0513(7) Uani 1 1 d . . . . .
H4A H 0.0822 0.6841 0.3101 0.062 Uiso 1 1 calc R . . . .
H4B H 0.1447 0.7498 0.2965 0.062 Uiso 1 1 calc R . . . .
C5 C 0.3199(3) 0.69078(11) 0.33873(13) 0.0457(7) Uani 1 1 d . . . . .
C6 C 0.3768(3) 0.63069(11) 0.36446(14) 0.0473(7) Uani 1 1 d . . . . .
C7 C 0.2848(4) 0.58112(12) 0.38873(15) 0.0543(7) Uani 1 1 d . . . . .
C8 C 0.5306(3) 0.62902(12) 0.35722(16) 0.0557(7) Uani 1 1 d . . . . .
C9 C 0.4415(3) 0.72034(11) 0.31714(14) 0.0496(7) Uani 1 1 d . . . . .
C10 C 0.4630(3) 0.77834(10) 0.27963(14) 0.0482(7) Uani 1 1 d . . . . .
C11 C 0.3973(3) 0.83425(11) 0.30887(16) 0.0505(7) Uani 1 1 d . . . . .
C12 C 0.4159(4) 0.84446(12) 0.38464(18) 0.0681(9) Uani 1 1 d . . . . .
H12 H 0.4769 0.8174 0.4174 0.082 Uiso 1 1 calc R . . . .
C13 C 0.3454(5) 0.89424(15) 0.4122(2) 0.0871(11) Uani 1 1 d . . . . .
H13 H 0.3608 0.9009 0.4631 0.105 Uiso 1 1 calc R . . . .
C14 C 0.2529(5) 0.93368(15) 0.3644(3) 0.0911(12) Uani 1 1 d . . . . .
H14 H 0.2028 0.9665 0.3828 0.109 Uiso 1 1 calc R . . . .
C15 C 0.2340(4) 0.92471(14) 0.2884(2) 0.0861(11) Uani 1 1 d . . . . .
H15 H 0.1733 0.9519 0.2557 0.103 Uiso 1 1 calc R . . . .
C16 C 0.3063(3) 0.87493(12) 0.26172(17) 0.0641(8) Uani 1 1 d . . . . .
H16 H 0.2930 0.8689 0.2108 0.077 Uiso 1 1 calc R . . . .
C17 C 0.7955(4) 0.59843(14) 0.3609(3) 0.1152(16) Uani 1 1 d . . . . .
H17A H 0.8384 0.6333 0.3899 0.173 Uiso 1 1 calc GR . . . .
H17B H 0.7903 0.6072 0.3093 0.173 Uiso 1 1 calc GR . . . .
H17C H 0.8620 0.5633 0.3748 0.173 Uiso 1 1 calc GR . . . .
C18 C 0.2882(4) 0.47822(13) 0.4300(2) 0.1016(13) Uani 1 1 d . . . . .
H18A H 0.2501 0.4892 0.4740 0.152 Uiso 1 1 calc GR . . . .
H18B H 0.3594 0.4440 0.4403 0.152 Uiso 1 1 calc GR . . . .
H18C H 0.2006 0.4670 0.3917 0.152 Uiso 1 1 calc GR . . . .


_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 C8 1.344(3) . ?
O1 C9 1.408(3) . ?
O2 C8 1.323(3) . ?
O2 C17 1.440(3) . ?
O3 C7 1.338(3) . ?
O3 C18 1.438(3) . ?
O4 C7 1.189(3) . ?
C1 C2 1.504(4) . ?
C2 C3 1.519(3) . ?
C3 C4 1.522(3) . ?
C4 C5 1.494(3) . ?
C5 C6 1.443(3) . ?
C5 C9 1.352(3) . ?
C6 C7 1.457(3) . ?
C6 C8 1.358(3) . ?
C9 C10 1.466(3) . ?
C10 C10 1.363(5) 2_655 ?
C10 C11 1.484(3) . ?
C11 C12 1.389(4) . ?
C11 C16 1.375(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.371(5) . ?
C14 C15 1.389(5) . ?
C15 C16 1.384(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 106.42(19) . . ?
C8 O2 C17 117.9(2) . . ?
C7 O3 C18 116.4(2) . . ?
C1 C2 C3 113.8(3) . . ?
C2 C3 C4 111.5(2) . . ?
C5 C4 C3 115.4(2) . . ?
C6 C5 C4 128.1(2) . . ?
C9 C5 C4 124.8(2) . . ?
C9 C5 C6 107.0(2) . . ?
C5 C6 C7 126.8(2) . . ?
C8 C6 C5 105.6(2) . . ?
C8 C6 C7 127.5(2) . . ?
O3 C7 C6 112.5(2) . . ?
O4 C7 O3 122.5(2) . . ?
O4 C7 C6 125.0(3) . . ?
O1 C8 C6 111.8(2) . . ?
O2 C8 O1 117.1(2) . . ?
O2 C8 C6 131.1(2) . . ?
O1 C9 C10 114.5(2) . . ?
C5 C9 O1 109.2(2) . . ?
C5 C9 C10 136.2(2) . . ?
C9 C10 C11 116.3(2) . . ?
C10 C10 C9 119.73(13) 2_655 . ?
C10 C10 C11 123.92(14) 2_655 . ?
C12 C11 C10 121.0(3) . . ?
C16 C11 C10 120.7(3) . . ?
C16 C11 C12 118.2(2) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C13 C12 119.8(3) . . ?
C13 C14 C15 120.0(3) . . ?
C16 C15 C14 119.4(3) . . ?
C11 C16 C15 121.4(3) . . ?

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

data_xuzhenghu
_database_code_depnum_ccdc_archive 'CCDC 1021787'
_audit_update_record             
;
2014-08-29 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_audit_creation_date             2014-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        'alkyne amide'
_chemical_formula_moiety         'C33 H41 N O9'
_chemical_formula_sum            'C33 H41 N O9'
_chemical_formula_weight         595.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.7518(3)
_cell_length_b                   17.4971(5)
_cell_length_c                   20.0458(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.206(3)
_cell_angle_gamma                90.00
_cell_volume                     3355.18(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3362
_cell_measurement_temperature    298.5(2)
_cell_measurement_theta_max      70.0530
_cell_measurement_theta_min      5.1430
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11896
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.50
_diffrn_ambient_temperature      298.5(2)
_diffrn_detector_area_resol_mean 16.0450
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega   69.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   53.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   73.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega  -13.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
  7 omega  -14.00   18.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   79.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00  125.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   93.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   87.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   93.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   83.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 15 omega   60.00  104.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   75.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   66.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000   30.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0912926000
_diffrn_orient_matrix_UB_12      0.0722284000
_diffrn_orient_matrix_UB_13      0.0144470000
_diffrn_orient_matrix_UB_21      -0.0317034000
_diffrn_orient_matrix_UB_22      0.0196848000
_diffrn_orient_matrix_UB_23      -0.0763896000
_diffrn_orient_matrix_UB_31      -0.1287842000
_diffrn_orient_matrix_UB_32      0.0463253000
_diffrn_orient_matrix_UB_33      0.0099588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3562
_reflns_number_total             5840
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.226
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+3.1076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2060
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C15(H15A,H15B), C22(H22A,H22B), C31(H31A,H31B),
 C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8), C10(H10), C25(H25)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,
 H9B,H9C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.9810(3) -0.27962(16) -0.05167(13) 0.0618(8) Uani 1 d . . .
O3 O 1.1311(3) -0.05531(18) -0.06201(17) 0.0730(9) Uani 1 d . . .
O4 O 0.9365(4) 0.03299(19) -0.15836(17) 0.0833(10) Uani 1 d . . .
O5 O 1.0702(4) -0.3020(2) -0.14086(15) 0.0876(11) Uani 1 d . . .
O6 O 0.7055(4) 0.0106(2) -0.1775(2) 0.1068(14) Uani 1 d . . .
O7 O 1.3136(3) -0.3919(2) -0.09714(17) 0.0822(10) Uani 1 d . . .
O8 O 0.9673(4) -0.27988(18) 0.17236(14) 0.0821(10) Uani 1 d . . .
O10 O 1.4137(4) -0.4028(2) 0.01525(19) 0.0846(10) Uani 1 d . . .
O11 O 1.0080(3) -0.13028(15) -0.00770(14) 0.0577(7) Uani 1 d . . .
N18 N 0.8598(4) -0.3797(2) 0.10949(18) 0.0697(11) Uani 1 d . . .
C1 C 0.6198(5) -0.2323(3) 0.0708(3) 0.0768(14) Uani 1 d . . .
H1 H 0.6198 -0.2803 0.0509 0.092 Uiso 1 calc . . R
C2 C 1.2576(5) -0.0860(3) -0.0159(3) 0.0840(15) Uani 1 d . . .
H2A H 1.2626 -0.1403 -0.0221 0.126 Uiso 1 calc . . GR
H2B H 1.2519 -0.0752 0.0304 0.126 Uiso 1 calc . . GR
H2C H 1.3396 -0.0623 -0.0264 0.126 Uiso 1 calc . . GR
C3 C 0.9050(7) 0.0950(3) -0.2068(3) 0.1017(19) Uani 1 d . . .
H3A H 0.8546 0.0754 -0.2493 0.153 Uiso 1 calc . . GR
H3B H 0.9905 0.1180 -0.2136 0.153 Uiso 1 calc . . GR
H3C H 0.8490 0.1325 -0.1896 0.153 Uiso 1 calc . . GR
C4 C 1.2678(7) -0.4889(3) 0.1777(3) 0.0946(17) Uani 1 d . . .
H4A H 1.3678 -0.4803 0.1850 0.114 Uiso 1 calc . . R
H4B H 1.2323 -0.4633 0.2138 0.114 Uiso 1 calc . . R
C5 C 0.6226(5) -0.0901(3) 0.1280(2) 0.0772(14) Uani 1 d . . .
H5 H 0.6211 -0.0420 0.1477 0.093 Uiso 1 calc . . R
C6 C 0.7905(5) -0.4157(3) 0.0446(2) 0.0775(14) Uani 1 d . . .
H6A H 0.6939 -0.4249 0.0457 0.116 Uiso 1 calc . . GR
H6B H 0.8358 -0.4633 0.0388 0.116 Uiso 1 calc . . GR
H6C H 0.7971 -0.3823 0.0074 0.116 Uiso 1 calc . . GR
C7 C 0.8548(8) -0.4219(3) 0.1706(3) 0.116(2) Uani 1 d . . .
H7A H 0.9312 -0.4066 0.2059 0.174 Uiso 1 calc . . GR
H7B H 0.8617 -0.4756 0.1620 0.174 Uiso 1 calc . . GR
H7C H 0.7680 -0.4116 0.1848 0.174 Uiso 1 calc . . GR
C8 C 0.5158(6) -0.2119(3) 0.1015(3) 0.0939(18) Uani 1 d . . .
H8 H 0.4425 -0.2455 0.1031 0.113 Uiso 1 calc . . R
C9 C 1.4434(6) -0.4227(3) -0.1079(3) 0.1014(19) Uani 1 d . . .
H9A H 1.4370 -0.4334 -0.1553 0.152 Uiso 1 calc . . GR
H9B H 1.4637 -0.4690 -0.0822 0.152 Uiso 1 calc . . GR
H9C H 1.5168 -0.3863 -0.0932 0.152 Uiso 1 calc . . GR
C10 C 0.5181(6) -0.1414(4) 0.1306(3) 0.0898(17) Uani 1 d . . .
H10 H 0.4465 -0.1278 0.1528 0.108 Uiso 1 calc . . R
C11 C 0.9654(7) -0.2487(4) -0.1782(3) 0.120(3) Uani 1 d . . .
H11A H 0.9778 -0.2444 -0.2244 0.179 Uiso 1 calc . . GR
H11B H 0.9769 -0.1994 -0.1569 0.179 Uiso 1 calc . . GR
H11C H 0.8733 -0.2676 -0.1776 0.179 Uiso 1 calc . . GR
C12 C 0.5690(6) -0.1694(5) -0.1455(3) 0.125(3) Uani 1 d . . .
H12A H 0.6044 -0.1533 -0.1852 0.150 Uiso 1 calc . . R
H12B H 0.6135 -0.2177 -0.1307 0.150 Uiso 1 calc . . R
C13 C 1.2390(8) -0.5740(4) 0.1802(3) 0.130(3) Uani 1 d . . .
H13A H 1.2628 -0.5984 0.1410 0.195 Uiso 1 calc . . GR
H13B H 1.1416 -0.5821 0.1803 0.195 Uiso 1 calc . . GR
H13C H 1.2943 -0.5954 0.2207 0.195 Uiso 1 calc . . GR
C14 C 0.3778(11) -0.2409(5) -0.2244(4) 0.193(5) Uani 1 d . . .
H14A H 0.4127 -0.2239 -0.2635 0.290 Uiso 1 calc . . GR
H14B H 0.2778 -0.2452 -0.2358 0.290 Uiso 1 calc . . GR
H14C H 0.4174 -0.2898 -0.2101 0.290 Uiso 1 calc . . GR
C15 C 0.4179(10) -0.1837(6) -0.1670(4) 0.166(4) Uani 1 d . . .
H15A H 0.3720 -0.1356 -0.1811 0.200 Uiso 1 calc . . R
H15B H 0.3820 -0.2018 -0.1280 0.200 Uiso 1 calc . . R
C16 C 1.0060(4) -0.0784(2) -0.0565(2) 0.0560(10) Uani 1 d . . .
C17 C 1.3149(5) -0.3827(2) -0.0320(3) 0.0642(11) Uani 1 d . . .
C18 C 0.8646(4) -0.1465(2) -0.0127(2) 0.0543(10) Uani 1 d . . .
C19 C 0.7785(4) -0.1047(2) -0.0630(2) 0.0540(10) Uani 1 d . . .
C20 C 0.8711(4) -0.0594(2) -0.0925(2) 0.0542(10) Uani 1 d . . .
C21 C 0.8256(5) -0.0030(2) -0.1469(2) 0.0610(11) Uani 1 d . . .
C22 C 0.6187(5) -0.1090(3) -0.0875(2) 0.0756(13) Uani 1 d . . .
H22A H 0.5849 -0.0590 -0.1038 0.091 Uiso 1 calc . . R
H22B H 0.5762 -0.1215 -0.0489 0.091 Uiso 1 calc . . R
C23 C 0.8412(4) -0.2021(2) 0.0361(2) 0.0529(10) Uani 1 d . . .
C24 C 0.7273(4) -0.1817(2) 0.0686(2) 0.0554(10) Uani 1 d . . .
C25 C 0.7271(5) -0.1097(2) 0.0969(2) 0.0631(11) Uani 1 d . . .
H25 H 0.7986 -0.0753 0.0944 0.076 Uiso 1 calc . . R
C26 C 0.9196(4) -0.2663(2) 0.05333(19) 0.0522(10) Uani 1 d . . .
C27 C 1.0193(4) -0.2955(2) 0.01825(19) 0.0518(9) Uani 1 d . . .
C28 C 1.1413(4) -0.3370(2) 0.0356(2) 0.0537(10) Uani 1 d . . .
C29 C 1.1845(4) -0.3471(2) -0.0261(2) 0.0569(10) Uani 1 d . . .
C30 C 1.0840(5) -0.3112(2) -0.0753(2) 0.0620(11) Uani 1 d . . .
C31 C 1.2169(5) -0.3689(2) 0.1042(2) 0.0633(11) Uani 1 d . . .
H31A H 1.3159 -0.3573 0.1103 0.076 Uiso 1 calc . . R
H31B H 1.1809 -0.3443 0.1406 0.076 Uiso 1 calc . . R
C32 C 1.1973(5) -0.4552(3) 0.1083(2) 0.0683(12) Uani 1 d . . .
H32A H 1.2361 -0.4797 0.0727 0.082 Uiso 1 calc . . R
H32B H 1.0981 -0.4667 0.1002 0.082 Uiso 1 calc . . R
C33 C 0.9163(5) -0.3093(2) 0.1167(2) 0.0589(11) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C27 1.406(4) . ?
O2 C30 1.312(5) . ?
O3 C2 1.490(6) . ?
O3 C16 1.311(5) . ?
O4 C3 1.448(5) . ?
O4 C21 1.310(5) . ?
O5 C11 1.476(6) . ?
O5 C30 1.305(5) . ?
O6 C21 1.235(5) . ?
O7 C9 1.430(5) . ?
O7 C17 1.314(5) . ?
O8 C33 1.242(5) . ?
O10 C17 1.262(6) . ?
O11 C16 1.331(4) . ?
O11 C18 1.411(5) . ?
N18 C6 1.484(6) . ?
N18 C7 1.440(6) . ?
N18 C33 1.345(5) . ?
C1 H1 0.9300 . ?
C1 C8 1.333(6) . ?
C1 C24 1.379(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C13 1.518(8) . ?
C4 C32 1.545(6) . ?
C5 H5 0.9300 . ?
C5 C10 1.367(7) . ?
C5 C25 1.338(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C10 1.363(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C15 1.474(9) . ?
C12 C22 1.575(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C15 1.517(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C20 1.412(6) . ?
C17 C29 1.442(6) . ?
C18 C19 1.388(5) . ?
C18 C23 1.430(5) . ?
C19 C20 1.414(5) . ?
C19 C22 1.542(6) . ?
C20 C21 1.473(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.438(5) . ?
C23 C26 1.364(5) . ?
C24 C25 1.382(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.402(5) . ?
C26 C33 1.482(5) . ?
C27 C28 1.379(6) . ?
C28 C29 1.393(5) . ?
C28 C31 1.534(6) . ?
C29 C30 1.398(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.527(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C30 O2 C27 101.7(3) . . ?
C16 O3 C2 120.5(3) . . ?
C21 O4 C3 113.8(4) . . ?
C30 O5 C11 120.9(3) . . ?
C17 O7 C9 111.0(4) . . ?
C16 O11 C18 102.2(3) . . ?
C7 N18 C6 116.3(4) . . ?
C33 N18 C6 126.2(4) . . ?
C33 N18 C7 117.3(4) . . ?
C8 C1 H1 120.2 . . ?
C8 C1 C24 119.6(5) . . ?
C24 C1 H1 120.2 . . ?
O3 C2 H2A 109.5 . . ?
O3 C2 H2B 109.5 . . ?
O3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C3 H3A 109.5 . . ?
O4 C3 H3B 109.5 . . ?
O4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C13 C4 H4A 109.5 . . ?
C13 C4 H4B 109.5 . . ?
C13 C4 C32 110.5(5) . . ?
C32 C4 H4A 109.5 . . ?
C32 C4 H4B 109.5 . . ?
C10 C5 H5 120.3 . . ?
C25 C5 H5 120.3 . . ?
C25 C5 C10 119.3(5) . . ?
N18 C6 H6A 109.5 . . ?
N18 C6 H6B 109.5 . . ?
N18 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N18 C7 H7A 109.5 . . ?
N18 C7 H7B 109.5 . . ?
N18 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 H8 120.4 . . ?
C1 C8 C10 119.2(5) . . ?
C10 C8 H8 120.4 . . ?
O7 C9 H9A 109.5 . . ?
O7 C9 H9B 109.5 . . ?
O7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10 119.0 . . ?
C8 C10 C5 122.0(5) . . ?
C8 C10 H10 119.0 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H12A C12 H12B 107.1 . . ?
C15 C12 H12A 107.7 . . ?
C15 C12 H12B 107.7 . . ?
C15 C12 C22 118.5(6) . . ?
C22 C12 H12A 107.7 . . ?
C22 C12 H12B 107.7 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
C12 C15 C14 115.5(8) . . ?
C12 C15 H15A 108.4 . . ?
C12 C15 H15B 108.4 . . ?
C14 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
O3 C16 O11 113.1(4) . . ?
O3 C16 C20 132.4(4) . . ?
O11 C16 C20 114.5(3) . . ?
O7 C17 C29 107.3(4) . . ?
O10 C17 O7 124.8(4) . . ?
O10 C17 C29 128.0(4) . . ?
O11 C18 C23 112.0(3) . . ?
C19 C18 O11 113.4(3) . . ?
C19 C18 C23 134.6(4) . . ?
C18 C19 C20 104.7(3) . . ?
C18 C19 C22 129.5(4) . . ?
C20 C19 C22 125.7(4) . . ?
C16 C20 C21 130.8(4) . . ?
C19 C20 C16 105.1(3) . . ?
C19 C20 C21 124.0(4) . . ?
O4 C21 C20 108.2(4) . . ?
O6 C21 O4 123.7(4) . . ?
O6 C21 C20 128.1(4) . . ?
C12 C22 H22A 108.6 . . ?
C12 C22 H22B 108.6 . . ?
C19 C22 C12 114.5(4) . . ?
C19 C22 H22A 108.6 . . ?
C19 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C18 C23 C24 112.4(3) . . ?
C26 C23 C18 125.3(3) . . ?
C26 C23 C24 122.3(3) . . ?
C1 C24 C23 120.9(4) . . ?
C1 C24 C25 120.7(4) . . ?
C25 C24 C23 118.4(4) . . ?
C5 C25 C24 119.1(4) . . ?
C5 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C23 C26 C27 125.6(3) . . ?
C23 C26 C33 122.1(3) . . ?
C27 C26 C33 112.1(3) . . ?
C26 C27 O2 110.6(3) . . ?
C28 C27 O2 113.9(3) . . ?
C28 C27 C26 135.5(4) . . ?
C27 C28 C29 103.8(4) . . ?
C27 C28 C31 131.2(4) . . ?
C29 C28 C31 125.0(4) . . ?
C28 C29 C17 123.5(4) . . ?
C28 C29 C30 106.1(4) . . ?
C30 C29 C17 130.1(4) . . ?
O2 C30 C29 114.5(3) . . ?
O5 C30 O2 112.1(4) . . ?
O5 C30 C29 133.4(4) . . ?
C28 C31 H31A 109.4 . . ?
C28 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 C28 111.4(4) . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C4 C32 H32A 109.0 . . ?
C4 C32 H32B 109.0 . . ?
C31 C32 C4 112.8(4) . . ?
C31 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
O8 C33 N18 124.0(4) . . ?
O8 C33 C26 119.2(4) . . ?
N18 C33 C26 116.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C27 C28 C29 0.9(4) . . . . ?
O2 C27 C28 C31 -177.4(4) . . . . ?
O3 C16 C20 C19 179.1(4) . . . . ?
O3 C16 C20 C21 -4.0(8) . . . . ?
O7 C17 C29 C28 171.9(4) . . . . ?
O7 C17 C29 C30 -14.0(6) . . . . ?
O10 C17 C29 C28 -7.5(7) . . . . ?
O10 C17 C29 C30 166.5(5) . . . . ?
O11 C16 C20 C19 -0.1(5) . . . . ?
O11 C16 C20 C21 176.8(4) . . . . ?
O11 C18 C19 C20 0.4(5) . . . . ?
O11 C18 C19 C22 175.8(4) . . . . ?
O11 C18 C23 C24 136.1(4) . . . . ?
O11 C18 C23 C26 -41.3(6) . . . . ?
C1 C8 C10 C5 1.4(10) . . . . ?
C1 C24 C25 C5 1.6(7) . . . . ?
C2 O3 C16 O11 -0.7(6) . . . . ?
C2 O3 C16 C20 -179.9(4) . . . . ?
C3 O4 C21 O6 4.7(7) . . . . ?
C3 O4 C21 C20 -174.9(4) . . . . ?
C6 N18 C33 O8 176.3(4) . . . . ?
C6 N18 C33 C26 -5.1(7) . . . . ?
C7 N18 C33 O8 2.0(7) . . . . ?
C7 N18 C33 C26 -179.5(5) . . . . ?
C8 C1 C24 C23 179.7(5) . . . . ?
C8 C1 C24 C25 -1.1(8) . . . . ?
C9 O7 C17 O10 -4.1(7) . . . . ?
C9 O7 C17 C29 176.4(4) . . . . ?
C10 C5 C25 C24 -0.5(7) . . . . ?
C11 O5 C30 O2 11.5(7) . . . . ?
C11 O5 C30 C29 -168.6(5) . . . . ?
C13 C4 C32 C31 177.2(5) . . . . ?
C15 C12 C22 C19 173.5(6) . . . . ?
C16 O11 C18 C19 -0.5(4) . . . . ?
C16 O11 C18 C23 -179.9(3) . . . . ?
C16 C20 C21 O4 -1.5(6) . . . . ?
C16 C20 C21 O6 178.9(5) . . . . ?
C17 C29 C30 O2 -175.3(4) . . . . ?
C17 C29 C30 O5 4.7(9) . . . . ?
C18 O11 C16 O3 -179.0(3) . . . . ?
C18 O11 C16 C20 0.4(4) . . . . ?
C18 C19 C20 C16 -0.2(4) . . . . ?
C18 C19 C20 C21 -177.4(4) . . . . ?
C18 C19 C22 C12 -88.0(6) . . . . ?
C18 C23 C24 C1 127.8(5) . . . . ?
C18 C23 C24 C25 -51.4(5) . . . . ?
C18 C23 C26 C27 -12.0(7) . . . . ?
C18 C23 C26 C33 162.2(4) . . . . ?
C19 C18 C23 C24 -43.2(6) . . . . ?
C19 C18 C23 C26 139.4(5) . . . . ?
C19 C20 C21 O4 174.9(4) . . . . ?
C19 C20 C21 O6 -4.7(7) . . . . ?
C20 C19 C22 C12 86.5(6) . . . . ?
C22 C12 C15 C14 178.4(7) . . . . ?
C22 C19 C20 C16 -175.8(4) . . . . ?
C22 C19 C20 C21 7.0(7) . . . . ?
C23 C18 C19 C20 179.7(4) . . . . ?
C23 C18 C19 C22 -4.9(8) . . . . ?
C23 C24 C25 C5 -179.3(4) . . . . ?
C23 C26 C27 O2 -31.7(6) . . . . ?
C23 C26 C27 C28 150.3(5) . . . . ?
C23 C26 C33 O8 -68.9(6) . . . . ?
C23 C26 C33 N18 112.4(5) . . . . ?
C24 C1 C8 C10 -0.3(9) . . . . ?
C24 C23 C26 C27 170.9(4) . . . . ?
C24 C23 C26 C33 -14.9(6) . . . . ?
C25 C5 C10 C8 -1.0(9) . . . . ?
C26 C23 C24 C1 -54.8(6) . . . . ?
C26 C23 C24 C25 126.1(5) . . . . ?
C26 C27 C28 C29 178.8(4) . . . . ?
C26 C27 C28 C31 0.5(8) . . . . ?
C27 O2 C30 O5 -179.1(4) . . . . ?
C27 O2 C30 C29 0.9(5) . . . . ?
C27 C26 C33 O8 106.0(5) . . . . ?
C27 C26 C33 N18 -72.6(5) . . . . ?
C27 C28 C29 C17 175.0(4) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C27 C28 C31 C32 105.1(5) . . . . ?
C28 C29 C30 O2 -0.4(5) . . . . ?
C28 C29 C30 O5 179.6(5) . . . . ?
C28 C31 C32 C4 -177.9(4) . . . . ?
C29 C28 C31 C32 -72.9(5) . . . . ?
C30 O2 C27 C26 -179.6(3) . . . . ?
C30 O2 C27 C28 -1.2(4) . . . . ?
C31 C28 C29 C17 -6.6(6) . . . . ?
C31 C28 C29 C30 178.1(4) . . . . ?
C33 C26 C27 O2 153.5(3) . . . . ?
C33 C26 C27 C28 -24.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
