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

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

data_Boger26
_database_code_depnum_ccdc_archive 'CCDC 1475225'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_audit_creation_date             2015-04-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ysl-cycloaddition-pro-Allyl
_chemical_formula_moiety         'C27 H32 N2 O7'
_chemical_formula_sum            'C27 H32 N2 O7'
_chemical_formula_weight         496.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.067(5)
_cell_length_b                   9.572(4)
_cell_length_c                   14.080(7)
_cell_angle_alpha                89.833(15)
_cell_angle_beta                 82.205(18)
_cell_angle_gamma                85.541(16)
_cell_volume                     1207.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4507
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.980
_cell_measurement_theta_min      2.274
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.7339.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20627
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.134
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3618
_reflns_number_total             4889
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.034
_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)+(0.0490P)²+0.3050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1092
_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 Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C20(H20A,
 H20B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_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 0.38774(14) 0.39297(13) 0.27269(9) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.10118(12) 0.31564(11) 0.80951(8) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.26398(13) 0.62987(12) 0.85970(9) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.02811(13) 0.56427(12) 0.89349(9) 0.0245(3) Uani 1 1 d . . . . .
O5 O 0.02837(14) -0.11833(12) 0.74342(9) 0.0304(3) Uani 1 1 d . . . . .
O6 O 0.36558(13) 0.35541(12) 0.93614(9) 0.0261(3) Uani 1 1 d . . . . .
O7 O 0.57738(13) 0.31660(12) 0.83277(8) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.25354(16) 0.51570(14) 0.60775(10) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.06462(15) 0.11052(14) 0.72316(10) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.25039(18) 0.43766(17) 0.52428(12) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.32775(19) 0.45666(17) 0.43420(12) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.3928 0.5299 0.4227 0.028 Uiso 1 1 calc R . . . .
C3 C 0.30780(19) 0.36481(18) 0.35989(13) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.21368(19) 0.25680(18) 0.37533(13) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.1999 0.1968 0.3242 0.030 Uiso 1 1 calc R . . . .
C5 C 0.13926(19) 0.23806(18) 0.46823(13) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.0747 0.1645 0.4799 0.028 Uiso 1 1 calc R . . . .
C6 C 0.15886(18) 0.32534(17) 0.54281(12) 0.0206(4) Uani 1 1 d . . . . .
C7 C 0.09059(18) 0.33122(17) 0.64679(12) 0.0206(4) Uani 1 1 d . . . . .
C8 C 0.13808(18) 0.47260(18) 0.68256(12) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.0513 0.5446 0.6929 0.025 Uiso 1 1 calc R . . . .
C9 C 0.19425(18) 0.42784(17) 0.78126(12) 0.0201(4) Uani 1 1 d . . . . .
C10 C 0.16955(19) 0.54996(17) 0.85108(12) 0.0209(4) Uani 1 1 d . . . . .
C11 C -0.07699(19) 0.30204(18) 0.66272(13) 0.0235(4) Uani 1 1 d . . . . .
H11A H -0.1317 0.3594 0.7166 0.028 Uiso 1 1 calc R . . . .
H11B H -0.1237 0.3235 0.6042 0.028 Uiso 1 1 calc R . . . .
C12 C -0.07812(19) 0.14484(18) 0.68608(13) 0.0251(4) Uani 1 1 d . . . . .
H12A H -0.1637 0.1269 0.7350 0.030 Uiso 1 1 calc R . . . .
H12B H -0.0839 0.0890 0.6278 0.030 Uiso 1 1 calc R . . . .
C13 C 0.14950(18) 0.22990(17) 0.72262(12) 0.0202(4) Uani 1 1 d . . . . .
C14 C 0.31908(18) 0.20318(17) 0.72741(12) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.33110(19) 0.08933(17) 0.80484(13) 0.0228(4) Uani 1 1 d . . . . .
H15A H 0.4373 0.0680 0.8129 0.027 Uiso 1 1 calc R . . . .
H15B H 0.2770 0.1250 0.8669 0.027 Uiso 1 1 calc R . . . .
C16 C 0.2654(2) -0.04450(18) 0.77691(14) 0.0254(4) Uani 1 1 d . . . . .
H16A H 0.3333 -0.0902 0.7230 0.030 Uiso 1 1 calc R . . . .
H16B H 0.2617 -0.1095 0.8318 0.030 Uiso 1 1 calc R . . . .
C17 C 0.10999(19) -0.02237(18) 0.74773(12) 0.0228(4) Uani 1 1 d . . . . .
C18 C 0.35324(18) 0.35274(17) 0.76418(12) 0.0197(4) Uani 1 1 d . . . . .
H18 H 0.4165 0.4010 0.7124 0.024 Uiso 1 1 calc R . . . .
C19 C 0.42826(18) 0.34428(16) 0.85478(13) 0.0206(4) Uani 1 1 d . . . . .
C20 C 0.41102(19) 0.15782(18) 0.63023(13) 0.0232(4) Uani 1 1 d . . . . .
H20A H 0.3647 0.0787 0.6040 0.028 Uiso 1 1 calc R . . . .
H20B H 0.4054 0.2367 0.5849 0.028 Uiso 1 1 calc R . . . .
C21 C 0.5755(2) 0.1133(2) 0.63542(14) 0.0294(4) Uani 1 1 d . . . . .
H21A H 0.6270 0.0918 0.5708 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.5828 0.0299 0.6756 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.6220 0.1897 0.6633 0.044 Uiso 1 1 calc GR . . . .
C22 C 0.6626(2) 0.29672(19) 0.91414(13) 0.0280(4) Uani 1 1 d . . . . .
H22A H 0.6236 0.3664 0.9650 0.034 Uiso 1 1 calc R . . . .
H22B H 0.7688 0.3119 0.8929 0.034 Uiso 1 1 calc R . . . .
C23 C 0.6510(2) 0.1523(2) 0.95354(13) 0.0316(4) Uani 1 1 d . . . . .
H23 H 0.5590 0.1309 0.9892 0.038 Uiso 1 1 calc R . . . .
C24 C 0.7610(3) 0.0529(2) 0.94175(15) 0.0454(6) Uani 1 1 d . . . . .
H24A H 0.8544 0.0712 0.9064 0.055 Uiso 1 1 calc R . . . .
H24B H 0.7470 -0.0371 0.9685 0.055 Uiso 1 1 calc R . . . .
C25 C 0.3631(2) 0.3133(2) 0.19115(14) 0.0369(5) Uani 1 1 d . . . . .
H25A H 0.4252 0.3450 0.1339 0.055 Uiso 1 1 calc GR . . . .
H25B H 0.2577 0.3267 0.1822 0.055 Uiso 1 1 calc GR . . . .
H25C H 0.3897 0.2138 0.2015 0.055 Uiso 1 1 calc GR . . . .
C26 C 0.2852(2) 0.66244(17) 0.60389(14) 0.0277(4) Uani 1 1 d . . . . .
H26A H 0.3697 0.6749 0.5541 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.3100 0.6916 0.6661 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.1971 0.7198 0.5889 0.042 Uiso 1 1 calc GR . . . .
C27 C -0.0116(2) 0.68960(18) 0.95235(13) 0.0274(4) Uani 1 1 d . . . . .
H27A H 0.0023 0.7728 0.9124 0.041 Uiso 1 1 calc GR . . . .
H27B H 0.0524 0.6900 1.0031 0.041 Uiso 1 1 calc GR . . . .
H27C H -0.1163 0.6905 0.9812 0.041 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 C3 1.376(2) . ?
O1 C25 1.432(2) . ?
O2 C9 1.4392(19) . ?
O2 C13 1.472(2) . ?
O3 C10 1.210(2) . ?
O4 C10 1.336(2) . ?
O4 C27 1.454(2) . ?
O5 C17 1.230(2) . ?
O6 C19 1.209(2) . ?
O7 C19 1.351(2) . ?
O7 C22 1.471(2) . ?
N1 C1 1.399(2) . ?
N1 C8 1.463(2) . ?
N1 C26 1.455(2) . ?
N2 C12 1.474(2) . ?
N2 C13 1.426(2) . ?
N2 C17 1.364(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.411(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.408(3) . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.406(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 C7 1.510(2) . ?
C7 C8 1.557(2) . ?
C7 C11 1.553(2) . ?
C7 C13 1.560(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.590(3) . ?
C9 C10 1.513(2) . ?
C9 C18 1.549(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.550(2) . ?
C14 C15 1.548(2) . ?
C14 C18 1.591(2) . ?
C14 C20 1.547(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.519(3) . ?
C18 H18 1.0000 . ?
C18 C19 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.530(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.494(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.318(3) . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C3 O1 C25 117.88(14) . . ?
C9 O2 C13 95.66(11) . . ?
C10 O4 C27 115.19(13) . . ?
C19 O7 C22 116.34(14) . . ?
C1 N1 C8 109.29(13) . . ?
C1 N1 C26 121.50(14) . . ?
C26 N1 C8 118.25(14) . . ?
C13 N2 C12 111.40(13) . . ?
C17 N2 C12 122.49(13) . . ?
C17 N2 C13 125.96(14) . . ?
N1 C1 C6 110.93(14) . . ?
C2 C1 N1 127.93(15) . . ?
C2 C1 C6 121.08(15) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.35(15) . . ?
C3 C2 H2 120.8 . . ?
O1 C3 C2 114.17(15) . . ?
O1 C3 C4 124.15(16) . . ?
C4 C3 C2 121.68(16) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.65(16) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.81(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 108.96(14) . . ?
C5 C6 C1 119.32(16) . . ?
C5 C6 C7 131.61(15) . . ?
C6 C7 C8 103.10(13) . . ?
C6 C7 C11 113.60(14) . . ?
C6 C7 C13 121.76(14) . . ?
C8 C7 C13 99.95(13) . . ?
C11 C7 C8 119.19(14) . . ?
C11 C7 C13 99.59(13) . . ?
N1 C8 C7 105.51(13) . . ?
N1 C8 H8 111.2 . . ?
N1 C8 C9 115.41(14) . . ?
C7 C8 H8 111.2 . . ?
C7 C8 C9 101.63(13) . . ?
C9 C8 H8 111.2 . . ?
O2 C9 C8 100.89(12) . . ?
O2 C9 C10 113.26(13) . . ?
O2 C9 C18 103.17(13) . . ?
C10 C9 C8 110.28(14) . . ?
C10 C9 C18 116.88(14) . . ?
C18 C9 C8 111.04(13) . . ?
O3 C10 O4 125.48(15) . . ?
O3 C10 C9 123.09(15) . . ?
O4 C10 C9 111.13(14) . . ?
C7 C11 H11A 110.7 . . ?
C7 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 C7 104.99(14) . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
N2 C12 C11 104.18(13) . . ?
N2 C12 H12A 110.9 . . ?
N2 C12 H12B 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O2 C13 C7 99.21(13) . . ?
O2 C13 C14 101.22(12) . . ?
N2 C13 O2 110.46(13) . . ?
N2 C13 C7 105.69(14) . . ?
N2 C13 C14 117.42(14) . . ?
C14 C13 C7 120.89(13) . . ?
C13 C14 C18 99.83(12) . . ?
C15 C14 C13 104.85(13) . . ?
C15 C14 C18 111.94(14) . . ?
C20 C14 C13 113.49(14) . . ?
C20 C14 C15 111.97(14) . . ?
C20 C14 C18 113.84(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 110.94(15) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C15 114.69(14) . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
O5 C17 N2 120.34(16) . . ?
O5 C17 C16 122.90(16) . . ?
N2 C17 C16 116.73(14) . . ?
C9 C18 C14 101.12(13) . . ?
C9 C18 H18 110.0 . . ?
C14 C18 H18 110.0 . . ?
C19 C18 C9 112.67(14) . . ?
C19 C18 C14 112.70(13) . . ?
C19 C18 H18 110.0 . . ?
O6 C19 O7 123.27(16) . . ?
O6 C19 C18 125.99(15) . . ?
O7 C19 C18 110.69(14) . . ?
C14 C20 H20A 108.6 . . ?
C14 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 C14 114.55(15) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 C23 110.59(14) . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C22 C23 H23 118.1 . . ?
C24 C23 C22 123.8(2) . . ?
C24 C23 H23 118.1 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_Boger47
_database_code_depnum_ccdc_archive 'CCDC 1475226'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_audit_creation_date             2016-04-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ysl-acid-unnatural
_chemical_formula_moiety         'C24 H30 N2 O6, C H2 Cl2'
_chemical_formula_sum            'C25 H32 Cl2 N2 O6'
_chemical_formula_weight         527.42
_chemical_absolute_configuration ad
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.8529(8)
_cell_length_b                   15.3187(15)
_cell_length_c                   20.944(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2519.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6045
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      52.791
_cell_measurement_theta_min      3.575
_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.586
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.8020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1212 before and 0.0838 after correction.
The Ratio of minimum to maximum transmission is 0.8059.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.097
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18667
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        59.122
_diffrn_reflns_theta_max         59.122
_diffrn_reflns_theta_min         3.575
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'Bruker Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Pt-135'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2521
_reflns_number_total             3603
_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 v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.082
_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)+(0.1059P)²+0.6059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 Cl2S-C1S = Cl2B-C1S = Cl1S-C1S = Cl1B-C1S
 1.8 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Cl1S, Cl2S, Cl1B, Cl2B, C1S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(Cl1S)=Sof(Cl2S)=Sof(H1SD)=Sof(H1SC)=1-FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(H1SB)=Sof(H1SA)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C1S(H1SB,H1SA),
 C1S(H1SD,H1SC)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C17(H17), C19(H19), C20(H20)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_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 0.4330(6) 1.1075(3) 0.4703(2) 0.0537(12) Uani 1 1 d . . . . .
H1 H 0.3758 1.1126 0.5029 0.081 Uiso 1 1 calc GR . . . .
O2 O 0.6672(7) 1.2456(4) 0.4952(3) 0.0767(16) Uani 1 1 d . . . . .
O3 O 0.8381(7) 1.2291(3) 0.5775(2) 0.0670(14) Uani 1 1 d . . . . .
H3 H 0.8812 1.2737 0.5632 0.100 Uiso 1 1 calc GR . . . .
O4 O 0.8842(9) 0.6674(4) 0.6227(3) 0.0874(18) Uani 1 1 d . . . . .
O5 O 0.6527(7) 1.0903(4) 0.3742(3) 0.0801(17) Uani 1 1 d . . . . .
O6 O 0.8702(6) 1.0853(3) 0.4425(2) 0.0582(13) Uani 1 1 d . . . . .
N1 N 0.2725(7) 1.0614(4) 0.5770(3) 0.0586(16) Uani 1 1 d . . . . .
N2 N 0.7226(7) 0.9167(4) 0.4970(3) 0.0542(15) Uani 1 1 d . . . . .
C1 C 0.1989(10) 1.1247(5) 0.6222(4) 0.067(2) Uani 1 1 d . . . . .
H1A H 0.1483 1.0941 0.6581 0.081 Uiso 1 1 calc R . . . .
H1B H 0.1106 1.1585 0.6013 0.081 Uiso 1 1 calc R . . . .
C2 C 0.3351(10) 1.1831(5) 0.6449(4) 0.066(2) Uani 1 1 d . . . . .
H2 H 0.3030 1.2345 0.6653 0.079 Uiso 1 1 calc R . . . .
C3 C 0.4972(10) 1.1678(5) 0.6385(3) 0.062(2) Uani 1 1 d . . . . .
H3A H 0.5724 1.2108 0.6521 0.075 Uiso 1 1 calc R . . . .
C4 C 0.5726(8) 1.0856(4) 0.6107(3) 0.0459(16) Uani 1 1 d . . . . .
C5 C 0.4281(8) 1.0189(4) 0.6000(3) 0.0500(17) Uani 1 1 d . . . . .
H5 H 0.4018 0.9928 0.6415 0.060 Uiso 1 1 calc R . . . .
C6 C 0.4565(8) 0.9436(4) 0.5526(3) 0.0495(17) Uani 1 1 d . . . . .
C7 C 0.5626(9) 0.9684(4) 0.4927(3) 0.0509(17) Uani 1 1 d . . . . .
H7 H 0.4999 0.9486 0.4549 0.061 Uiso 1 1 calc R . . . .
C8 C 0.5931(8) 1.0686(4) 0.4858(3) 0.0486(17) Uani 1 1 d . . . . .
C9 C 0.6746(8) 1.1043(4) 0.5471(3) 0.0419(15) Uani 1 1 d . . . . .
H9 H 0.7832 1.0734 0.5516 0.050 Uiso 1 1 calc R . . . .
C10 C 0.7207(9) 1.1997(5) 0.5368(3) 0.0549(18) Uani 1 1 d . . . . .
C11 C 0.7056(9) 1.0485(5) 0.6587(3) 0.0575(18) Uani 1 1 d . . . . .
H11A H 0.7500 0.9944 0.6414 0.069 Uiso 1 1 calc R . . . .
H11B H 0.7998 1.0893 0.6613 0.069 Uiso 1 1 calc R . . . .
C12 C 0.6428(12) 1.0305(7) 0.7266(4) 0.083(3) Uani 1 1 d . . . . .
H12A H 0.5656 0.9819 0.7261 0.124 Uiso 1 1 calc GR . . . .
H12B H 0.5852 1.0812 0.7428 0.124 Uiso 1 1 calc GR . . . .
H12C H 0.7381 1.0171 0.7536 0.124 Uiso 1 1 calc GR . . . .
C13 C 0.2668(9) 0.9166(6) 0.5349(5) 0.076(2) Uani 1 1 d . . . . .
H13A H 0.2542 0.9107 0.4891 0.091 Uiso 1 1 calc R . . . .
H13B H 0.2372 0.8615 0.5549 0.091 Uiso 1 1 calc R . . . .
C14 C 0.1540(9) 0.9894(6) 0.5599(4) 0.071(2) Uani 1 1 d . . . . .
H14A H 0.0742 1.0083 0.5273 0.085 Uiso 1 1 calc R . . . .
H14B H 0.0905 0.9702 0.5971 0.085 Uiso 1 1 calc R . . . .
C15 C 0.5547(9) 0.8688(4) 0.5811(3) 0.0524(18) Uani 1 1 d . . . . .
C16 C 0.7045(9) 0.8561(5) 0.5457(3) 0.0534(17) Uani 1 1 d . . . . .
C17 C 0.8138(10) 0.7870(5) 0.5607(4) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.9117 0.7772 0.5368 0.071 Uiso 1 1 calc R . . . .
C18 C 0.7737(11) 0.7331(5) 0.6119(4) 0.063(2) Uani 1 1 d . . . . .
C19 C 0.6263(12) 0.7478(5) 0.6477(4) 0.074(2) Uani 1 1 d . . . . .
H19 H 0.6009 0.7120 0.6823 0.088 Uiso 1 1 calc R . . . .
C20 C 0.5168(10) 0.8166(5) 0.6313(4) 0.071(2) Uani 1 1 d . . . . .
H20 H 0.4183 0.8263 0.6549 0.085 Uiso 1 1 calc R . . . .
C21 C 0.7039(10) 1.0829(5) 0.4271(4) 0.0599(19) Uani 1 1 d . . . . .
C22 C 0.7965(12) 0.8854(5) 0.4373(4) 0.075(2) Uani 1 1 d . . . . .
H22A H 0.7459 0.8304 0.4261 0.112 Uiso 1 1 calc GR . . . .
H22B H 0.9171 0.8780 0.4425 0.112 Uiso 1 1 calc GR . . . .
H22C H 0.7750 0.9270 0.4040 0.112 Uiso 1 1 calc GR . . . .
C23 C 0.8406(14) 0.6030(6) 0.6696(5) 0.102(3) Uani 1 1 d . . . . .
H23A H 0.7312 0.5785 0.6597 0.153 Uiso 1 1 calc GR . . . .
H23B H 0.8366 0.6298 0.7111 0.153 Uiso 1 1 calc GR . . . .
H23C H 0.9249 0.5576 0.6696 0.153 Uiso 1 1 calc GR . . . .
C24 C 0.9908(10) 1.0914(6) 0.3910(4) 0.077(2) Uani 1 1 d . . . . .
H24A H 0.9439 1.1266 0.3574 0.116 Uiso 1 1 calc GR . . . .
H24B H 1.0150 1.0341 0.3750 0.116 Uiso 1 1 calc GR . . . .
H24C H 1.0940 1.1177 0.4063 0.116 Uiso 1 1 calc GR . . . .
Cl1S Cl 0.785(3) 0.4104(13) 0.7406(10) 0.194(8) Uani 0.54(3) 1 d D U P A 1
Cl2S Cl 0.889(3) 0.2403(11) 0.7606(10) 0.261(10) Uani 0.54(3) 1 d D U P A 1
Cl1B Cl 0.889(3) 0.4230(7) 0.7737(9) 0.147(6) Uani 0.46(3) 1 d D U P A 2
Cl2B Cl 0.831(3) 0.2392(8) 0.7563(5) 0.151(5) Uani 0.46(3) 1 d D U P A 2
C1S C 0.956(2) 0.3316(8) 0.7385(8) 0.190(6) Uani 1 1 d D U . . .
H1SB H 1.0009 0.3274 0.6955 0.228 Uiso 0.46(3) 1 calc R . P A 1
H1SA H 1.0473 0.3505 0.7665 0.228 Uiso 0.46(3) 1 calc R . P A 1
H1SD H 1.0724 0.3204 0.7516 0.228 Uiso 0.54(3) 1 calc R . P A 2
H1SC H 0.9561 0.3404 0.6927 0.228 Uiso 0.54(3) 1 calc R . P A 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
O1 H1 0.8200 . ?
O1 C8 1.428(8) . ?
O2 C10 1.195(8) . ?
O3 H3 0.8200 . ?
O3 C10 1.334(8) . ?
O4 C18 1.348(9) . ?
O4 C23 1.434(10) . ?
O5 C21 1.184(9) . ?
O6 C21 1.346(9) . ?
O6 C24 1.437(9) . ?
N1 C1 1.473(9) . ?
N1 C5 1.466(8) . ?
N1 C14 1.487(10) . ?
N2 C7 1.489(8) . ?
N2 C16 1.385(9) . ?
N2 C22 1.460(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.473(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.302(10) . ?
C3 H3A 0.9300 . ?
C3 C4 1.507(10) . ?
C4 C5 1.543(10) . ?
C4 C9 1.580(9) . ?
C4 C11 1.559(9) . ?
C5 H5 0.9800 . ?
C5 C6 1.537(10) . ?
C6 C7 1.553(9) . ?
C6 C13 1.590(9) . ?
C6 C15 1.505(10) . ?
C7 H7 0.9800 . ?
C7 C8 1.561(9) . ?
C8 C9 1.534(9) . ?
C8 C21 1.523(10) . ?
C9 H9 0.9800 . ?
C9 C10 1.520(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.530(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.518(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.405(10) . ?
C15 C20 1.354(10) . ?
C16 C17 1.399(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(11) . ?
C18 C19 1.397(11) . ?
C19 H19 0.9300 . ?
C19 C20 1.403(11) . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Cl1S C1S 1.806(16) . ?
Cl2S C1S 1.565(19) . ?
Cl1B C1S 1.666(15) . ?
Cl2B C1S 1.762(18) . ?
C1S H1SB 0.9700 . ?
C1S H1SA 0.9700 . ?
C1S H1SD 0.9700 . ?
C1S H1SC 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
C8 O1 H1 109.5 . . ?
C10 O3 H3 109.5 . . ?
C18 O4 C23 118.4(7) . . ?
C21 O6 C24 117.5(6) . . ?
C1 N1 C14 113.4(6) . . ?
C5 N1 C1 114.1(6) . . ?
C5 N1 C14 105.7(5) . . ?
C16 N2 C7 108.3(5) . . ?
C16 N2 C22 116.8(6) . . ?
C22 N2 C7 117.3(6) . . ?
N1 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
N1 C1 C2 108.8(6) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
C1 C2 H2 117.7 . . ?
C3 C2 C1 124.5(8) . . ?
C3 C2 H2 117.7 . . ?
C2 C3 H3A 117.5 . . ?
C2 C3 C4 125.1(8) . . ?
C4 C3 H3A 117.5 . . ?
C3 C4 C5 108.7(5) . . ?
C3 C4 C9 111.9(5) . . ?
C3 C4 C11 108.6(6) . . ?
C5 C4 C9 111.7(5) . . ?
C5 C4 C11 110.2(5) . . ?
C11 C4 C9 105.7(5) . . ?
N1 C5 C4 111.5(5) . . ?
N1 C5 H5 107.2 . . ?
N1 C5 C6 104.1(5) . . ?
C4 C5 H5 107.2 . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 H5 107.2 . . ?
C5 C6 C7 114.5(5) . . ?
C5 C6 C13 102.1(5) . . ?
C7 C6 C13 112.2(6) . . ?
C15 C6 C5 113.0(5) . . ?
C15 C6 C7 103.4(5) . . ?
C15 C6 C13 112.0(6) . . ?
N2 C7 C6 105.9(5) . . ?
N2 C7 H7 107.9 . . ?
N2 C7 C8 113.6(5) . . ?
C6 C7 H7 107.9 . . ?
C6 C7 C8 113.4(5) . . ?
C8 C7 H7 107.9 . . ?
O1 C8 C7 107.2(5) . . ?
O1 C8 C9 114.2(5) . . ?
O1 C8 C21 105.0(5) . . ?
C9 C8 C7 109.7(5) . . ?
C21 C8 C7 107.7(5) . . ?
C21 C8 C9 112.7(6) . . ?
C4 C9 H9 105.8 . . ?
C8 C9 C4 115.4(5) . . ?
C8 C9 H9 105.8 . . ?
C10 C9 C4 114.5(5) . . ?
C10 C9 C8 108.9(5) . . ?
C10 C9 H9 105.8 . . ?
O2 C10 O3 120.6(7) . . ?
O2 C10 C9 125.8(7) . . ?
O3 C10 C9 113.5(6) . . ?
C4 C11 H11A 108.1 . . ?
C4 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 C4 116.7(6) . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 110.5 . . ?
C6 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C6 106.0(6) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
N1 C14 C13 105.3(6) . . ?
N1 C14 H14A 110.7 . . ?
N1 C14 H14B 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C6 108.9(6) . . ?
C20 C15 C6 130.2(7) . . ?
C20 C15 C16 120.9(7) . . ?
N2 C16 C15 112.5(6) . . ?
N2 C16 C17 127.6(6) . . ?
C17 C16 C15 120.0(6) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(7) . . ?
C18 C17 H17 120.5 . . ?
O4 C18 C17 115.3(7) . . ?
O4 C18 C19 124.3(7) . . ?
C17 C18 C19 120.4(7) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(7) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.9(7) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
O5 C21 O6 123.5(7) . . ?
O5 C21 C8 125.1(7) . . ?
O6 C21 C8 111.4(6) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl1S C1S H1SB 109.7 . . ?
Cl1S C1S H1SA 109.7 . . ?
Cl2S C1S Cl1S 109.8(12) . . ?
Cl2S C1S H1SB 109.7 . . ?
Cl2S C1S H1SA 109.7 . . ?
Cl1B C1S Cl2B 114.0(9) . . ?
Cl1B C1S H1SD 108.7 . . ?
Cl1B C1S H1SC 108.7 . . ?
Cl2B C1S H1SD 108.7 . . ?
Cl2B C1S H1SC 108.7 . . ?
H1SB C1S H1SA 108.2 . . ?
H1SD C1S H1SC 107.6 . . ?

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
O1 H1 N1 0.82 1.92 2.661(7) 149.8 .
O3 H3 O1 0.82 1.99 2.797(7) 167.2 4_576

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_THETM01_Boger47             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Did not diffract past 0.9 A.
;
_vrf_PLAT340_Boger47             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01009 Ang.  
RESPONSE: Room temperature data collection due to phase transition of the crystals.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_Boger48
_database_code_depnum_ccdc_archive 'CCDC 1475227'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_audit_creation_date             2016-04-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ysl-518-OBn-natural
_chemical_formula_moiety         'C31 H38 N2 O5'
_chemical_formula_sum            'C31 H38 N2 O5'
_chemical_formula_weight         518.63
_chemical_absolute_configuration ad
_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 0.0181 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'

_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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   27.2685(8)
_cell_length_b                   27.2685(8)
_cell_length_c                   7.6863(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5715.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      53.837
_cell_measurement_theta_min      2.292
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.3142
_exptl_absorpt_correction_T_min  0.2227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.7088.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2224
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13691
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        63.241
_diffrn_reflns_theta_max         63.241
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3331
_reflns_number_total             4523
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1399
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C31B) = Uanis(C31)
3. Rigid body (RIGU) restrains
 O3, O3B, N2, N2B, C6, C7, C15, C16, C17, C18, C19, C20, C22, C30, C15B, C16B,
 C17B, C18B, C19B, C20B, C22B, C30B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O4, O5, O4B, O5B, C21, C31, C21B, C31B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: O3(0.6) O4(0.6) O5(0.6) O3B(0.4) O4B(0.4) O5B(0.4) N2(0.6)
 N2B(0.4) H7(0.6) H7B(0.4) C15(0.6) C16(0.6) C17(0.6) H17(0.6) C18(0.6)
 C19(0.6) H19(0.6) C20(0.6) H20(0.6) C21(0.6) C22(0.6) H22A(0.6) H22B(0.6)
 H22C(0.6) C30(0.6) H30A(0.6) H30B(0.6) H30C(0.6) C31(0.6) H31A(0.6) H31B(0.6)
 H31C(0.6) C15B(0.4) C16B(0.4) C17B(0.4) H17B(0.4) C18B(0.4) C19B(0.4)
 H19B(0.4) C20B(0.4) H20B(0.4) C21B(0.4) C22B(0.4) H22D(0.4) H22E(0.4)
 H22F(0.4) C30B(0.4) H30D(0.4) H30E(0.4) H30F(0.4) C31B(0.4) H31D(0.4)
 H31E(0.4) H31F(0.4)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C7(H7B), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C17(H17),
 C19(H19), C20(H20), C17B(H17B), C19B(H19B), C20B(H20B)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C22B(H22D,H22E,H22F), C30B(H30D,H30E,H30F), C31B(H31D,H31E,H31F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_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 0.87415(15) 0.56888(13) 0.2833(5) 0.0669(10) Uani 1 1 d . . . . .
H1 H 0.8609 0.5854 0.2039 0.100 Uiso 1 1 calc GR . . . .
O2 O 0.75668(12) 0.56168(11) 0.6487(5) 0.0554(8) Uani 1 1 d . . . . .
O3 O 0.8913(3) 0.8445(3) 0.7745(10) 0.0742(17) Uani 0.6 1 d . U P A 1
O4 O 0.9353(5) 0.5354(5) 0.4922(16) 0.068(4) Uani 0.6 1 d . U P B 1
O5 O 0.8991(7) 0.5755(8) 0.718(2) 0.058(3) Uani 0.6 1 d . U P B 1
O3B O 0.9172(4) 0.8138(4) 0.8541(12) 0.055(2) Uani 0.4 1 d . U P A 2
O4B O 0.8918(11) 0.5647(13) 0.753(3) 0.061(6) Uani 0.4 1 d . U P C 2
O5B O 0.9445(8) 0.5478(7) 0.534(2) 0.056(4) Uani 0.4 1 d . U P C 2
N1 N 0.82793(14) 0.63941(15) 0.1022(5) 0.0511(10) Uani 1 1 d . . . . .
N2 N 0.9152(4) 0.6728(4) 0.5821(12) 0.052(2) Uani 0.6 1 d . U P A 1
N2B N 0.9262(7) 0.6631(7) 0.538(3) 0.070(5) Uani 0.4 1 d . U P A 2
C1 C 0.78236(19) 0.6272(2) 0.0114(7) 0.0597(13) Uani 1 1 d . . . . .
H1A H 0.7891 0.6024 -0.0797 0.072 Uiso 1 1 calc R . . . .
H1B H 0.7691 0.6569 -0.0459 0.072 Uiso 1 1 calc R . . . .
C2 C 0.74587(19) 0.60768(18) 0.1349(7) 0.0545(12) Uani 1 1 d . . . . .
H2 H 0.7183 0.5906 0.0894 0.065 Uiso 1 1 calc R . . . .
C3 C 0.74939(17) 0.61269(17) 0.3065(6) 0.0474(11) Uani 1 1 d . . . . .
H3 H 0.7247 0.5980 0.3763 0.057 Uiso 1 1 calc R . . . .
C4 C 0.79002(16) 0.64023(15) 0.3983(5) 0.0387(10) Uani 1 1 d . . . . .
C5 C 0.81946(16) 0.66855(16) 0.2611(5) 0.0418(10) Uani 1 1 d . . . . .
H5 H 0.8002 0.6983 0.2279 0.050 Uiso 1 1 calc R . . . .
C6 C 0.87176(17) 0.68518(16) 0.3081(6) 0.0437(10) Uani 1 1 d . U . . .
C7 C 0.90261(18) 0.64581(18) 0.4055(7) 0.0545(12) Uani 1 1 d . U . . .
H7 H 0.9335 0.6391 0.3396 0.065 Uiso 0.6 1 calc R . P A 1
H7B H 0.9289 0.6367 0.3208 0.065 Uiso 0.4 1 calc R . P A 2
C8 C 0.87491(18) 0.59682(18) 0.4399(7) 0.0536(12) Uani 1 1 d . . . . .
C9 C 0.82332(16) 0.60507(16) 0.5107(6) 0.0440(11) Uani 1 1 d . . . . .
H9 H 0.8272 0.6210 0.6270 0.053 Uiso 1 1 calc R . . . .
C10 C 0.79958(18) 0.55551(17) 0.5431(8) 0.0561(13) Uani 1 1 d . . . . .
H10A H 0.7904 0.5403 0.4307 0.067 Uiso 1 1 calc R . . . .
H10B H 0.8231 0.5335 0.6026 0.067 Uiso 1 1 calc R . . . .
C11 C 0.76516(16) 0.67650(15) 0.5271(6) 0.0423(10) Uani 1 1 d . . . . .
H11A H 0.7473 0.6571 0.6156 0.051 Uiso 1 1 calc R . . . .
H11B H 0.7912 0.6949 0.5883 0.051 Uiso 1 1 calc R . . . .
C12 C 0.7295(2) 0.71339(19) 0.4476(7) 0.0588(13) Uani 1 1 d . . . . .
H12A H 0.7064 0.6962 0.3714 0.088 Uiso 1 1 calc GR . . . .
H12B H 0.7478 0.7377 0.3797 0.088 Uiso 1 1 calc GR . . . .
H12C H 0.7114 0.7300 0.5406 0.088 Uiso 1 1 calc GR . . . .
C13 C 0.8929(2) 0.6973(2) 0.1272(7) 0.0616(14) Uani 1 1 d . . . . .
H13A H 0.8907 0.7329 0.1038 0.074 Uiso 1 1 calc R . . . .
H13B H 0.9277 0.6872 0.1198 0.074 Uiso 1 1 calc R . . . .
C14 C 0.8619(2) 0.6686(2) -0.0031(7) 0.0602(14) Uani 1 1 d . . . . .
H14A H 0.8438 0.6912 -0.0806 0.072 Uiso 1 1 calc R . . . .
H14B H 0.8829 0.6470 -0.0753 0.072 Uiso 1 1 calc R . . . .
C23 C 0.7324(2) 0.5168(2) 0.6755(10) 0.0805(19) Uani 1 1 d . . . . .
H23A H 0.7542 0.4940 0.7389 0.097 Uiso 1 1 calc R . . . .
H23B H 0.7242 0.5019 0.5618 0.097 Uiso 1 1 calc R . . . .
C24 C 0.6867(2) 0.52470(19) 0.7773(9) 0.0702(16) Uani 1 1 d . . . . .
C25 C 0.6745(3) 0.4932(3) 0.9073(12) 0.106(3) Uani 1 1 d . . . . .
H25 H 0.6950 0.4659 0.9310 0.127 Uiso 1 1 calc R . . . .
C26 C 0.6329(4) 0.5001(3) 1.0051(16) 0.142(4) Uani 1 1 d . . . . .
H26 H 0.6261 0.4785 1.0993 0.170 Uiso 1 1 calc R . . . .
C27 C 0.6021(3) 0.5361(3) 0.9704(14) 0.126(3) Uani 1 1 d . . . . .
H27 H 0.5717 0.5381 1.0304 0.151 Uiso 1 1 calc R . . . .
C28 C 0.6141(3) 0.5713(3) 0.8462(12) 0.109(3) Uani 1 1 d . . . . .
H28 H 0.5933 0.5986 0.8254 0.131 Uiso 1 1 calc R . . . .
C29 C 0.6567(3) 0.5653(3) 0.7552(10) 0.093(2) Uani 1 1 d . . . . .
H29 H 0.6661 0.5898 0.6738 0.111 Uiso 1 1 calc R . . . .
C15 C 0.8730(8) 0.7306(6) 0.420(2) 0.042(3) Uani 0.6 1 d . U P A 1
C16 C 0.8995(4) 0.7219(4) 0.5711(15) 0.043(2) Uani 0.6 1 d . U P A 1
C17 C 0.9076(4) 0.7585(5) 0.6983(12) 0.047(2) Uani 0.6 1 d . U P A 1
H17 H 0.9261 0.7522 0.8006 0.057 Uiso 0.6 1 calc R . P A 1
C18 C 0.8865(5) 0.8045(4) 0.6648(17) 0.050(2) Uani 0.6 1 d . U P A 1
C19 C 0.8598(4) 0.8140(4) 0.5169(16) 0.054(2) Uani 0.6 1 d . U P A 1
H19 H 0.8451 0.8451 0.4999 0.065 Uiso 0.6 1 calc R . P A 1
C20 C 0.8546(5) 0.7771(4) 0.3915(15) 0.051(3) Uani 0.6 1 d . U P A 1
H20 H 0.8383 0.7841 0.2853 0.061 Uiso 0.6 1 calc R . P A 1
C21 C 0.9071(6) 0.5672(6) 0.5461(18) 0.057(4) Uani 0.6 1 d . U P B 1
C22 C 0.9643(4) 0.6643(4) 0.6557(16) 0.065(3) Uani 0.6 1 d . U P A 1
H22A H 0.9739 0.6301 0.6355 0.097 Uiso 0.6 1 calc GR . P A 1
H22B H 0.9637 0.6708 0.7811 0.097 Uiso 0.6 1 calc GR . P A 1
H22C H 0.9880 0.6862 0.5996 0.097 Uiso 0.6 1 calc GR . P A 1
C30 C 0.9148(7) 0.8392(7) 0.9236(19) 0.100(4) Uani 0.6 1 d . U P A 1
H30A H 0.9487 0.8290 0.9010 0.150 Uiso 0.6 1 calc GR . P A 1
H30B H 0.8983 0.8142 0.9942 0.150 Uiso 0.6 1 calc GR . P A 1
H30C H 0.9149 0.8705 0.9864 0.150 Uiso 0.6 1 calc GR . P A 1
C31 C 0.9320(5) 0.5476(5) 0.8306(12) 0.093(3) Uani 0.6 1 d . U P B 1
H31A H 0.9279 0.5125 0.8079 0.139 Uiso 0.6 1 calc GR . P B 1
H31B H 0.9242 0.5545 0.9527 0.139 Uiso 0.6 1 calc GR . P B 1
H31C H 0.9660 0.5571 0.8068 0.139 Uiso 0.6 1 calc GR . P B 1
C15B C 0.8761(11) 0.7245(8) 0.451(3) 0.037(4) Uani 0.4 1 d . U P A 2
C16B C 0.9104(7) 0.7084(8) 0.573(2) 0.049(4) Uani 0.4 1 d . U P A 2
C17B C 0.9248(6) 0.7397(6) 0.7032(19) 0.050(4) Uani 0.4 1 d . U P A 2
H17B H 0.9502 0.7308 0.7817 0.060 Uiso 0.4 1 calc R . P A 2
C18B C 0.9011(5) 0.7852(8) 0.7178(17) 0.039(3) Uani 0.4 1 d . U P A 2
C19B C 0.8679(6) 0.8021(5) 0.601(2) 0.040(3) Uani 0.4 1 d . U P A 2
H19B H 0.8544 0.8341 0.6124 0.048 Uiso 0.4 1 calc R . P A 2
C20B C 0.8534(7) 0.7711(6) 0.4601(17) 0.036(3) Uani 0.4 1 d . U P A 2
H20B H 0.8296 0.7812 0.3770 0.044 Uiso 0.4 1 calc R . P A 2
C21B C 0.9011(8) 0.5668(9) 0.607(3) 0.053(5) Uani 0.4 1 d . U P C 2
C22B C 0.9773(8) 0.6482(8) 0.583(4) 0.113(10) Uani 0.4 1 d . U P A 2
H22D H 0.9780 0.6359 0.7031 0.170 Uiso 0.4 1 calc GR . P A 2
H22E H 0.9991 0.6766 0.5728 0.170 Uiso 0.4 1 calc GR . P A 2
H22F H 0.9882 0.6223 0.5038 0.170 Uiso 0.4 1 calc GR . P A 2
C30B C 0.8939(7) 0.8645(7) 0.871(4) 0.089(5) Uani 0.4 1 d . U P A 2
H30D H 0.8999 0.8833 0.7648 0.134 Uiso 0.4 1 calc GR . P A 2
H30E H 0.9085 0.8817 0.9706 0.134 Uiso 0.4 1 calc GR . P A 2
H30F H 0.8586 0.8610 0.8897 0.134 Uiso 0.4 1 calc GR . P A 2
C31B C 0.9702(7) 0.5182(7) 0.661(2) 0.093(3) Uani 0.4 1 d . U P C 2
H31D H 0.9963 0.4996 0.6027 0.139 Uiso 0.4 1 calc GR . P C 2
H31E H 0.9472 0.4955 0.7159 0.139 Uiso 0.4 1 calc GR . P C 2
H31F H 0.9847 0.5396 0.7496 0.139 Uiso 0.4 1 calc GR . 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
O1 H1 0.8400 . ?
O1 C8 1.425(6) . ?
O2 C10 1.434(6) . ?
O2 C23 1.406(6) . ?
O3 C18 1.384(14) . ?
O3 C30 1.321(17) . ?
O4 C21 1.230(17) . ?
O5 C21 1.359(18) . ?
O5 C31 1.460(18) . ?
O3B C18B 1.379(18) . ?
O3B C30B 1.53(2) . ?
O4B C21B 1.15(3) . ?
O5B C21B 1.41(3) . ?
O5B C31B 1.44(2) . ?
N1 C1 1.464(6) . ?
N1 C5 1.475(5) . ?
N1 C14 1.466(7) . ?
N2 C7 1.582(11) . ?
N2 C16 1.406(13) . ?
N2 C22 1.472(13) . ?
N2B C7 1.292(18) . ?
N2B C16B 1.34(2) . ?
N2B C22B 1.49(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.475(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.329(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.513(6) . ?
C4 C5 1.534(6) . ?
C4 C9 1.578(6) . ?
C4 C11 1.555(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.540(7) . ?
C6 C7 1.556(7) . ?
C6 C13 1.542(7) . ?
C6 C15 1.510(17) . ?
C6 C15B 1.54(3) . ?
C7 H7 1.0000 . ?
C7 H7B 1.0000 . ?
C7 C8 1.557(8) . ?
C8 C9 1.525(7) . ?
C8 C21 1.446(15) . ?
C8 C21B 1.68(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.487(9) . ?
C24 C25 1.360(10) . ?
C24 C29 1.388(9) . ?
C25 H25 0.9500 . ?
C25 C26 1.373(13) . ?
C26 H26 0.9500 . ?
C26 C27 1.320(13) . ?
C27 H27 0.9500 . ?
C27 C28 1.392(11) . ?
C28 H28 0.9500 . ?
C28 C29 1.365(11) . ?
C29 H29 0.9500 . ?
C15 C16 1.385(18) . ?
C15 C20 1.380(17) . ?
C16 C17 1.414(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.405(18) . ?
C18 C19 1.374(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.400(15) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C15B C16B 1.40(3) . ?
C15B C20B 1.41(3) . ?
C16B C17B 1.37(2) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.40(2) . ?
C18B C19B 1.36(2) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.43(2) . ?
C20B H20B 0.9500 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C30B H30D 0.9800 . ?
C30B H30E 0.9800 . ?
C30B H30F 0.9800 . ?
C31B H31D 0.9800 . ?
C31B H31E 0.9800 . ?
C31B H31F 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
C8 O1 H1 109.5 . . ?
C23 O2 C10 111.4(4) . . ?
C30 O3 C18 119.3(13) . . ?
C21 O5 C31 112.9(12) . . ?
C18B O3B C30B 116.5(15) . . ?
C21B O5B C31B 110.1(17) . . ?
C1 N1 C5 112.6(4) . . ?
C1 N1 C14 113.4(4) . . ?
C14 N1 C5 105.3(4) . . ?
C16 N2 C7 109.0(8) . . ?
C16 N2 C22 116.8(9) . . ?
C22 N2 C7 116.9(8) . . ?
C7 N2B C16B 109.7(13) . . ?
C7 N2B C22B 123.3(14) . . ?
C16B N2B C22B 120.3(16) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.4(4) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
C1 C2 H2 118.2 . . ?
C3 C2 C1 123.6(5) . . ?
C3 C2 H2 118.2 . . ?
C2 C3 H3 117.7 . . ?
C2 C3 C4 124.5(5) . . ?
C4 C3 H3 117.7 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 C9 112.0(3) . . ?
C3 C4 C11 107.1(4) . . ?
C5 C4 C9 112.4(3) . . ?
C5 C4 C11 110.2(3) . . ?
C11 C4 C9 106.8(3) . . ?
N1 C5 C4 112.3(3) . . ?
N1 C5 H5 108.0 . . ?
N1 C5 C6 102.0(3) . . ?
C4 C5 H5 108.0 . . ?
C4 C5 C6 118.1(4) . . ?
C6 C5 H5 108.0 . . ?
C5 C6 C7 114.3(4) . . ?
C5 C6 C13 101.4(4) . . ?
C13 C6 C7 112.3(4) . . ?
C15 C6 C5 113.4(8) . . ?
C15 C6 C7 106.2(6) . . ?
C15 C6 C13 109.3(8) . . ?
C15B C6 C5 116.4(12) . . ?
C15B C6 C7 95.6(8) . . ?
C15B C6 C13 117.6(11) . . ?
N2 C7 H7 109.7 . . ?
N2B C7 C6 113.4(8) . . ?
N2B C7 H7B 104.2 . . ?
N2B C7 C8 114.9(11) . . ?
C6 C7 N2 102.0(5) . . ?
C6 C7 H7 109.7 . . ?
C6 C7 H7B 104.2 . . ?
C6 C7 C8 114.3(4) . . ?
C8 C7 N2 111.1(6) . . ?
C8 C7 H7 109.7 . . ?
C8 C7 H7B 104.2 . . ?
O1 C8 C7 108.8(4) . . ?
O1 C8 C9 111.5(4) . . ?
O1 C8 C21 100.8(7) . . ?
O1 C8 C21B 113.1(10) . . ?
C7 C8 C21B 109.9(10) . . ?
C9 C8 C7 112.4(4) . . ?
C9 C8 C21B 101.0(8) . . ?
C21 C8 C7 106.3(8) . . ?
C21 C8 C9 116.2(7) . . ?
C4 C9 H9 106.6 . . ?
C8 C9 C4 115.2(4) . . ?
C8 C9 H9 106.6 . . ?
C10 C9 C4 112.6(4) . . ?
C10 C9 C8 108.7(4) . . ?
C10 C9 H9 106.6 . . ?
O2 C10 C9 109.6(4) . . ?
O2 C10 H10A 109.7 . . ?
O2 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C4 C11 H11A 108.2 . . ?
C4 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C4 116.2(4) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 110.5 . . ?
C6 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C6 105.9(4) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
N1 C14 C13 105.4(4) . . ?
N1 C14 H14A 110.7 . . ?
N1 C14 H14B 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
O2 C23 H23A 109.6 . . ?
O2 C23 H23B 109.6 . . ?
O2 C23 C24 110.3(5) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
C25 C24 C23 120.1(6) . . ?
C25 C24 C29 116.7(7) . . ?
C29 C24 C23 123.0(5) . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(7) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.1(8) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(8) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 121.0 . . ?
C29 C28 C27 118.0(7) . . ?
C29 C28 H28 121.0 . . ?
C24 C29 H29 118.9 . . ?
C28 C29 C24 122.3(6) . . ?
C28 C29 H29 118.9 . . ?
C16 C15 C6 110.4(10) . . ?
C20 C15 C6 130.7(11) . . ?
C20 C15 C16 118.8(13) . . ?
N2 C16 C17 125.6(10) . . ?
C15 C16 N2 111.8(10) . . ?
C15 C16 C17 122.5(10) . . ?
C16 C17 H17 121.9 . . ?
C18 C17 C16 116.1(10) . . ?
C18 C17 H17 121.9 . . ?
O3 C18 C17 123.6(14) . . ?
C19 C18 O3 114.0(10) . . ?
C19 C18 C17 122.4(10) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(10) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 C19 120.8(11) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O4 C21 O5 123.1(12) . . ?
O4 C21 C8 125.6(11) . . ?
O5 C21 C8 111.0(10) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 H31A 109.5 . . ?
O5 C31 H31B 109.5 . . ?
O5 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C16B C15B C6 108.2(16) . . ?
C16B C15B C20B 123(2) . . ?
C20B C15B C6 129.0(17) . . ?
N2B C16B C15B 111.7(17) . . ?
N2B C16B C17B 129.1(16) . . ?
C17B C16B C15B 119.1(19) . . ?
C16B C17B H17B 120.8 . . ?
C16B C17B C18B 118.5(14) . . ?
C18B C17B H17B 120.8 . . ?
O3B C18B C17B 114.5(13) . . ?
C19B C18B O3B 121.6(18) . . ?
C19B C18B C17B 123.7(14) . . ?
C18B C19B H19B 120.5 . . ?
C18B C19B C20B 119.0(13) . . ?
C20B C19B H19B 120.5 . . ?
C15B C20B C19B 116.7(16) . . ?
C15B C20B H20B 121.7 . . ?
C19B C20B H20B 121.7 . . ?
O4B C21B O5B 123.8(19) . . ?
O4B C21B C8 132.4(17) . . ?
O5B C21B C8 103.3(16) . . ?
N2B C22B H22D 109.5 . . ?
N2B C22B H22E 109.5 . . ?
N2B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O3B C30B H30D 109.5 . . ?
O3B C30B H30E 109.5 . . ?
O3B C30B H30F 109.5 . . ?
H30D C30B H30E 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?
O5B C31B H31D 109.5 . . ?
O5B C31B H31E 109.5 . . ?
O5B C31B H31F 109.5 . . ?
H31D C31B H31E 109.5 . . ?
H31D C31B H31F 109.5 . . ?
H31E C31B H31F 109.5 . . ?

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
O1 H1 N1 0.84 1.89 2.688(5) 157.0 .

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
O1 C8 C9 C4 -69.0(5) . . . . ?
O1 C8 C9 C10 58.5(5) . . . . ?
O1 C8 C21 O4 18(2) . . . . ?
O1 C8 C21 O5 -156.6(11) . . . . ?
O1 C8 C21B O4B -141(3) . . . . ?
O1 C8 C21B O5B 46.8(19) . . . . ?
O2 C23 C24 C25 -137.6(7) . . . . ?
O2 C23 C24 C29 37.6(9) . . . . ?
O3 C18 C19 C20 176.7(9) . . . . ?
O3B C18B C19B C20B 178.6(13) . . . . ?
N1 C1 C2 C3 16.1(7) . . . . ?
N1 C5 C6 C7 -80.7(4) . . . . ?
N1 C5 C6 C13 40.3(4) . . . . ?
N1 C5 C6 C15 157.4(7) . . . . ?
N1 C5 C6 C15B 169.2(10) . . . . ?
N2 C7 C8 O1 -167.2(5) . . . . ?
N2 C7 C8 C9 68.8(6) . . . . ?
N2 C7 C8 C21 -59.4(8) . . . . ?
N2 C16 C17 C18 -176.8(10) . . . . ?
N2B C7 C8 O1 -148.4(9) . . . . ?
N2B C7 C8 C9 87.6(9) . . . . ?
N2B C7 C8 C21B -24.1(12) . . . . ?
N2B C16B C17B C18B -177(2) . . . . ?
C1 N1 C5 C4 63.8(5) . . . . ?
C1 N1 C5 C6 -168.7(4) . . . . ?
C1 N1 C14 C13 153.9(4) . . . . ?
C1 C2 C3 C4 2.1(8) . . . . ?
C2 C3 C4 C5 10.6(6) . . . . ?
C2 C3 C4 C9 -113.9(5) . . . . ?
C2 C3 C4 C11 129.3(5) . . . . ?
C3 C4 C5 N1 -41.6(5) . . . . ?
C3 C4 C5 C6 -159.9(4) . . . . ?
C3 C4 C9 C8 109.2(4) . . . . ?
C3 C4 C9 C10 -16.2(5) . . . . ?
C3 C4 C11 C12 -57.9(5) . . . . ?
C4 C5 C6 C7 42.9(5) . . . . ?
C4 C5 C6 C13 163.9(4) . . . . ?
C4 C5 C6 C15 -78.9(8) . . . . ?
C4 C5 C6 C15B -67.1(10) . . . . ?
C4 C9 C10 O2 -65.5(5) . . . . ?
C5 N1 C1 C2 -48.1(5) . . . . ?
C5 N1 C14 C13 30.3(5) . . . . ?
C5 C4 C9 C8 -12.9(5) . . . . ?
C5 C4 C9 C10 -138.3(4) . . . . ?
C5 C4 C11 C12 59.5(5) . . . . ?
C5 C6 C7 N2 -120.6(6) . . . . ?
C5 C6 C7 N2B -134.9(12) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C5 C6 C13 C14 -22.2(5) . . . . ?
C5 C6 C15 C16 124.8(12) . . . . ?
C5 C6 C15 C20 -59(2) . . . . ?
C5 C6 C15B C16B 129.9(16) . . . . ?
C5 C6 C15B C20B -54(3) . . . . ?
C6 C7 C8 O1 78.1(5) . . . . ?
C6 C7 C8 C9 -45.9(6) . . . . ?
C6 C7 C8 C21 -174.1(7) . . . . ?
C6 C7 C8 C21B -157.6(9) . . . . ?
C6 C13 C14 N1 -3.9(5) . . . . ?
C6 C15 C16 N2 -3.5(18) . . . . ?
C6 C15 C16 C17 178.6(12) . . . . ?
C6 C15 C20 C19 179.4(16) . . . . ?
C6 C15B C16B N2B -4(3) . . . . ?
C6 C15B C16B C17B 172.8(18) . . . . ?
C6 C15B C20B C19B -174(2) . . . . ?
C7 N2 C16 C15 7.0(14) . . . . ?
C7 N2 C16 C17 -175.2(10) . . . . ?
C7 N2B C16B C15B -4(3) . . . . ?
C7 N2B C16B C17B 179(2) . . . . ?
C7 C6 C13 C14 100.2(5) . . . . ?
C7 C6 C15 C16 -1.5(16) . . . . ?
C7 C6 C15 C20 175.2(18) . . . . ?
C7 C6 C15B C16B 9.3(19) . . . . ?
C7 C6 C15B C20B -175(2) . . . . ?
C7 C8 C9 C4 53.5(5) . . . . ?
C7 C8 C9 C10 -179.0(4) . . . . ?
C7 C8 C21 O4 -95.9(19) . . . . ?
C7 C8 C21 O5 90.0(12) . . . . ?
C7 C8 C21B O4B 97(3) . . . . ?
C7 C8 C21B O5B -75.0(18) . . . . ?
C8 C9 C10 O2 165.6(4) . . . . ?
C9 C4 C5 N1 82.7(4) . . . . ?
C9 C4 C5 C6 -35.7(5) . . . . ?
C9 C4 C11 C12 -178.1(4) . . . . ?
C9 C8 C21 O4 138.2(16) . . . . ?
C9 C8 C21 O5 -36.0(13) . . . . ?
C9 C8 C21B O4B -22(3) . . . . ?
C9 C8 C21B O5B 166.1(15) . . . . ?
C10 O2 C23 C24 -177.0(5) . . . . ?
C11 C4 C5 N1 -158.3(3) . . . . ?
C11 C4 C5 C6 83.4(4) . . . . ?
C11 C4 C9 C8 -133.8(4) . . . . ?
C11 C4 C9 C10 100.7(4) . . . . ?
C13 C6 C7 N2 124.6(6) . . . . ?
C13 C6 C7 N2B 110.3(12) . . . . ?
C13 C6 C7 C8 -115.4(5) . . . . ?
C13 C6 C15 C16 -122.8(12) . . . . ?
C13 C6 C15 C20 54(2) . . . . ?
C13 C6 C15B C16B -109.4(16) . . . . ?
C13 C6 C15B C20B 67(3) . . . . ?
C14 N1 C1 C2 -167.6(4) . . . . ?
C14 N1 C5 C4 -172.1(4) . . . . ?
C14 N1 C5 C6 -44.7(4) . . . . ?
C23 O2 C10 C9 177.4(5) . . . . ?
C23 C24 C25 C26 178.9(9) . . . . ?
C23 C24 C29 C28 178.1(8) . . . . ?
C24 C25 C26 C27 3.5(18) . . . . ?
C25 C24 C29 C28 -6.5(11) . . . . ?
C25 C26 C27 C28 -7.3(19) . . . . ?
C26 C27 C28 C29 4.2(16) . . . . ?
C27 C28 C29 C24 2.9(13) . . . . ?
C29 C24 C25 C26 3.4(13) . . . . ?
C15 C6 C7 N2 5.1(10) . . . . ?
C15 C6 C7 C8 125.1(10) . . . . ?
C15 C6 C13 C14 -142.3(8) . . . . ?
C15 C16 C17 C18 0.7(17) . . . . ?
C16 N2 C7 C6 -7.4(9) . . . . ?
C16 N2 C7 C8 -129.6(7) . . . . ?
C16 C15 C20 C19 -4(2) . . . . ?
C16 C17 C18 O3 -179.1(9) . . . . ?
C16 C17 C18 C19 -0.3(14) . . . . ?
C17 C18 C19 C20 -2.3(16) . . . . ?
C18 C19 C20 C15 4.5(19) . . . . ?
C20 C15 C16 N2 179.3(15) . . . . ?
C20 C15 C16 C17 1(2) . . . . ?
C21 C8 C9 C4 176.3(8) . . . . ?
C21 C8 C9 C10 -56.2(9) . . . . ?
C22 N2 C7 C6 -142.5(9) . . . . ?
C22 N2 C7 C8 95.3(10) . . . . ?
C22 N2 C16 C15 142.3(13) . . . . ?
C22 N2 C16 C17 -40.0(16) . . . . ?
C30 O3 C18 C17 -3.4(15) . . . . ?
C30 O3 C18 C19 177.7(11) . . . . ?
C31 O5 C21 O4 8(2) . . . . ?
C31 O5 C21 C8 -178.0(17) . . . . ?
C15B C6 C7 N2B -12.6(16) . . . . ?
C15B C6 C7 C8 121.6(12) . . . . ?
C15B C6 C13 C14 -150.4(11) . . . . ?
C15B C16B C17B C18B 6(3) . . . . ?
C16B N2B C7 C6 11(2) . . . . ?
C16B N2B C7 C8 -122.7(16) . . . . ?
C16B C15B C20B C19B 1(3) . . . . ?
C16B C17B C18B O3B 178.8(14) . . . . ?
C16B C17B C18B C19B -6(2) . . . . ?
C17B C18B C19B C20B 4(2) . . . . ?
C18B C19B C20B C15B -2(2) . . . . ?
C20B C15B C16B N2B 179(2) . . . . ?
C20B C15B C16B C17B -4(3) . . . . ?
C21B C8 C9 C4 170.6(11) . . . . ?
C21B C8 C9 C10 -62.0(11) . . . . ?
C22B N2B C7 C6 -140.0(19) . . . . ?
C22B N2B C7 C8 86(2) . . . . ?
C22B N2B C16B C15B 148(2) . . . . ?
C22B N2B C16B C17B -29(4) . . . . ?
C30B O3B C18B C17B 177.7(15) . . . . ?
C30B O3B C18B C19B 2.8(19) . . . . ?
C31B O5B C21B O4B 10(3) . . . . ?
C31B O5B C21B C8 -176.7(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_Boger49
_database_code_depnum_ccdc_archive 'CCDC 1475228'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-11-03 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ysl-cycloaddition-pro-CO2Me-unnatural
_chemical_formula_moiety         'C25 H30 N2 O7'
_chemical_formula_sum            'C25 H30 N2 O7'
_chemical_formula_weight         470.51
_chemical_absolute_configuration ad
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.96580(10)
_cell_length_b                   14.5779(2)
_cell_length_c                   17.7311(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2317.50(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.156
_cell_measurement_theta_min      3.925
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.7272.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.168
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21459
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         68.259
_diffrn_reflns_theta_min         3.925
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4061
_reflns_number_total             4223
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.046
_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)+(0.0352P)²+0.4569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0725
_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 Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_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 0.83191(18) 0.74702(10) 0.55154(9) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.75151(16) 0.50187(9) 0.68729(7) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.46146(19) 0.50418(13) 0.78945(9) 0.0415(4) Uani 1 1 d . . . . .
O4 O 0.26972(18) 0.47263(13) 0.71316(9) 0.0415(4) Uani 1 1 d . . . . .
O5 O 0.5864(2) 0.24562(13) 0.31868(9) 0.0472(5) Uani 1 1 d . . . . .
O6 O 0.5810(2) 0.31065(13) 0.77886(9) 0.0438(4) Uani 1 1 d . . . . .
O7 O 0.79447(19) 0.38577(10) 0.80371(8) 0.0349(4) Uani 1 1 d . . . . .
N1 N 0.80307(18) 0.59886(11) 0.58261(9) 0.0228(3) Uani 1 1 d . . . . .
N2 N 0.6553(2) 0.29781(11) 0.58415(9) 0.0279(4) Uani 1 1 d . . . . .
C1 C 0.7504(2) 0.68579(13) 0.57394(11) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.5873(2) 0.70052(14) 0.59175(12) 0.0291(4) Uani 1 1 d . . . . .
H2A H 0.5312 0.7049 0.5438 0.035 Uiso 1 1 calc R . . . .
H2B H 0.5762 0.7598 0.6184 0.035 Uiso 1 1 calc R . . . .
C3 C 0.5176(2) 0.62508(14) 0.64006(11) 0.0283(4) Uani 1 1 d . . . . .
H3A H 0.4085 0.6347 0.6430 0.034 Uiso 1 1 calc R . . . .
H3B H 0.5585 0.6286 0.6918 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5494(2) 0.52949(14) 0.60700(11) 0.0246(4) Uani 1 1 d . . . . .
C5 C 0.7207(2) 0.52150(13) 0.60727(10) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.7987(2) 0.43656(13) 0.57149(11) 0.0227(4) Uani 1 1 d . . . . .
C7 C 0.7489(2) 0.36004(13) 0.62731(11) 0.0252(4) Uani 1 1 d . . . . .
H7 H 0.8370 0.3273 0.6489 0.030 Uiso 1 1 calc R . . . .
C8 C 0.6669(2) 0.41873(13) 0.68940(11) 0.0258(4) Uani 1 1 d . . . . .
C9 C 0.5105(2) 0.44853(14) 0.66366(11) 0.0260(4) Uani 1 1 d . . . . .
H9 H 0.4607 0.3973 0.6359 0.031 Uiso 1 1 calc R . . . .
C10 C 0.4150(2) 0.47821(16) 0.72972(12) 0.0303(5) Uani 1 1 d . . . . .
C11 C 0.4773(2) 0.51657(15) 0.52900(11) 0.0272(4) Uani 1 1 d . . . . .
H11A H 0.5296 0.5563 0.4923 0.033 Uiso 1 1 calc R . . . .
H11B H 0.4918 0.4522 0.5129 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3112(2) 0.53870(16) 0.52662(13) 0.0352(5) Uani 1 1 d . . . . .
H12A H 0.2696 0.5187 0.4782 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.2970 0.6050 0.5323 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.2603 0.5066 0.5678 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.9623(2) 0.46926(13) 0.57303(12) 0.0256(4) Uani 1 1 d . . . . .
H13A H 1.0100 0.4527 0.6215 0.031 Uiso 1 1 calc R . . . .
H13B H 1.0196 0.4409 0.5314 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9568(2) 0.57426(14) 0.56357(13) 0.0281(4) Uani 1 1 d . . . . .
H14A H 1.0281 0.6046 0.5981 0.034 Uiso 1 1 calc R . . . .
H14B H 0.9806 0.5921 0.5111 0.034 Uiso 1 1 calc R . . . .
C15 C 0.7504(2) 0.39913(13) 0.49631(11) 0.0235(4) Uani 1 1 d . . . . .
C16 C 0.6712(2) 0.31741(13) 0.50784(11) 0.0253(4) Uani 1 1 d . . . . .
C17 C 0.6163(3) 0.26742(15) 0.44771(12) 0.0320(5) Uani 1 1 d . . . . .
H17 H 0.5614 0.2126 0.4557 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6438(3) 0.29967(15) 0.37494(12) 0.0336(5) Uani 1 1 d . . . . .
C19 C 0.7244(3) 0.37992(15) 0.36224(11) 0.0320(5) Uani 1 1 d . . . . .
H19 H 0.7426 0.4008 0.3123 0.038 Uiso 1 1 calc R . . . .
C20 C 0.7778(2) 0.42904(13) 0.42396(11) 0.0267(4) Uani 1 1 d . . . . .
H20 H 0.8336 0.4836 0.4161 0.032 Uiso 1 1 calc R . . . .
C21 C 0.6726(3) 0.36802(15) 0.76345(11) 0.0302(5) Uani 1 1 d . . . . .
C22 C 0.6398(3) 0.20328(16) 0.60921(13) 0.0435(6) Uani 1 1 d . . . . .
H22A H 0.7298 0.1688 0.5959 0.065 Uiso 1 1 calc GR . . . .
H22B H 0.5531 0.1754 0.5846 0.065 Uiso 1 1 calc GR . . . .
H22C H 0.6259 0.2020 0.6640 0.065 Uiso 1 1 calc GR . . . .
C23 C 0.1686(3) 0.5012(3) 0.77280(16) 0.0589(8) Uani 1 1 d . . . . .
H23A H 0.0663 0.4843 0.7592 0.088 Uiso 1 1 calc GR . . . .
H23B H 0.1752 0.5678 0.7794 0.088 Uiso 1 1 calc GR . . . .
H23C H 0.1963 0.4706 0.8200 0.088 Uiso 1 1 calc GR . . . .
C24 C 0.6398(4) 0.2622(2) 0.24439(13) 0.0560(8) Uani 1 1 d . . . . .
H24A H 0.5967 0.2169 0.2098 0.084 Uiso 1 1 calc GR . . . .
H24B H 0.7488 0.2569 0.2437 0.084 Uiso 1 1 calc GR . . . .
H24C H 0.6107 0.3240 0.2285 0.084 Uiso 1 1 calc GR . . . .
C25 C 0.8122(4) 0.32863(18) 0.87032(13) 0.0465(6) Uani 1 1 d . . . . .
H25A H 0.8102 0.2639 0.8556 0.070 Uiso 1 1 calc GR . . . .
H25B H 0.7306 0.3409 0.9057 0.070 Uiso 1 1 calc GR . . . .
H25C H 0.9078 0.3426 0.8946 0.070 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 C1 1.220(2) . ?
O2 C5 1.474(2) . ?
O2 C8 1.430(2) . ?
O3 C10 1.199(3) . ?
O4 C10 1.338(3) . ?
O4 C23 1.454(3) . ?
O5 C18 1.371(3) . ?
O5 C24 1.422(3) . ?
O6 C21 1.204(3) . ?
O7 C21 1.331(3) . ?
O7 C25 1.454(3) . ?
N1 C1 1.361(3) . ?
N1 C5 1.417(3) . ?
N1 C14 1.463(3) . ?
N2 C7 1.453(3) . ?
N2 C16 1.390(3) . ?
N2 C22 1.455(3) . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.538(3) . ?
C4 C5 1.541(3) . ?
C4 C9 1.589(3) . ?
C4 C11 1.538(3) . ?
C5 C6 1.557(3) . ?
C6 C7 1.557(3) . ?
C6 C13 1.543(3) . ?
C6 C15 1.504(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.576(3) . ?
C8 C9 1.538(3) . ?
C8 C21 1.508(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.514(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.541(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.402(3) . ?
C15 C20 1.377(3) . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(3) . ?
C18 C19 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C8 O2 C5 95.19(13) . . ?
C10 O4 C23 115.47(18) . . ?
C18 O5 C24 116.74(19) . . ?
C21 O7 C25 114.47(18) . . ?
C1 N1 C5 126.51(16) . . ?
C1 N1 C14 121.93(16) . . ?
C5 N1 C14 111.52(15) . . ?
C7 N2 C22 119.07(17) . . ?
C16 N2 C7 108.97(16) . . ?
C16 N2 C22 120.13(17) . . ?
O1 C1 N1 120.67(18) . . ?
O1 C1 C2 122.93(18) . . ?
N1 C1 C2 116.39(17) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C1 C2 C3 114.22(17) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.29(16) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 C5 104.58(16) . . ?
C3 C4 C9 113.05(16) . . ?
C5 C4 C9 99.24(16) . . ?
C11 C4 C3 112.08(17) . . ?
C11 C4 C5 114.35(16) . . ?
C11 C4 C9 112.68(16) . . ?
O2 C5 C4 101.80(14) . . ?
O2 C5 C6 98.84(14) . . ?
N1 C5 O2 110.73(15) . . ?
N1 C5 C4 117.29(17) . . ?
N1 C5 C6 105.86(14) . . ?
C4 C5 C6 120.43(16) . . ?
C7 C6 C5 100.49(14) . . ?
C13 C6 C5 100.01(15) . . ?
C13 C6 C7 118.88(16) . . ?
C15 C6 C5 121.35(17) . . ?
C15 C6 C7 102.76(15) . . ?
C15 C6 C13 113.68(16) . . ?
N2 C7 C6 106.14(15) . . ?
N2 C7 H7 111.1 . . ?
N2 C7 C8 115.97(17) . . ?
C6 C7 H7 111.1 . . ?
C6 C7 C8 100.89(15) . . ?
C8 C7 H7 111.1 . . ?
O2 C8 C7 101.23(14) . . ?
O2 C8 C9 103.67(15) . . ?
O2 C8 C21 114.87(16) . . ?
C9 C8 C7 111.78(16) . . ?
C21 C8 C7 109.06(17) . . ?
C21 C8 C9 115.33(17) . . ?
C4 C9 H9 110.0 . . ?
C8 C9 C4 101.40(15) . . ?
C8 C9 H9 110.0 . . ?
C10 C9 C4 113.64(17) . . ?
C10 C9 C8 111.52(16) . . ?
C10 C9 H9 110.0 . . ?
O3 C10 O4 123.4(2) . . ?
O3 C10 C9 125.25(19) . . ?
O4 C10 C9 111.31(18) . . ?
C4 C11 H11A 108.7 . . ?
C4 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C4 114.16(17) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 110.5 . . ?
C6 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C6 105.94(16) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
N1 C14 C13 104.39(16) . . ?
N1 C14 H14A 110.9 . . ?
N1 C14 H14B 110.9 . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 C6 108.96(16) . . ?
C20 C15 C6 131.25(18) . . ?
C20 C15 C16 119.70(18) . . ?
N2 C16 C15 111.63(17) . . ?
C17 C16 N2 127.30(19) . . ?
C17 C16 C15 121.05(19) . . ?
C16 C17 H17 120.9 . . ?
C16 C17 C18 118.23(19) . . ?
C18 C17 H17 120.9 . . ?
O5 C18 C17 114.39(19) . . ?
O5 C18 C19 124.02(19) . . ?
C19 C18 C17 121.6(2) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.89(19) . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 120.51(18) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
O6 C21 O7 125.01(19) . . ?
O6 C21 C8 121.0(2) . . ?
O7 C21 C8 113.55(18) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 H25A 109.5 . . ?
O7 C25 H25B 109.5 . . ?
O7 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
