 
data_ka96
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C20 H29 N O5' 
_chemical_formula_sum
 'C20 H29 N O5' 
_chemical_formula_weight          363.44

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.1212(17)
_cell_length_b                    14.764(4)
_cell_length_c                    22.957(6)
_cell_angle_alpha                 97.013(6)
_cell_angle_beta                  97.345(6)
_cell_angle_gamma                 100.970(6)
_cell_volume                      1997.1(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     4666
_cell_measurement_theta_min       3
_cell_measurement_theta_max       30
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.209          
_exptl_crystal_F_000              784
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.350
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     0.086
_shelx_estimated_absorpt_T_min    0.970
_shelx_estimated_absorpt_T_max    0.991
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.3413  
_exptl_absorpt_correction_T_max   0.4330
_exptl_absorpt_process_details    'APEX2 (Bruker, 2005)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             22768
_diffrn_reflns_av_unetI/netI      0.0916
_diffrn_reflns_v_R_equivalents    0.0710
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          0.905
_diffrn_reflns_theta_max          26.999
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              8669
_reflns_number_gt                 5880
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'APEX2 (Bruker, 2005)'
_computing_cell_refinement        'APEX2 (Bruker, 2005)'
_computing_data_reduction         'APEX2 (Bruker, 2005)'
_computing_structure_solution     'APEX2 (Bruker, 2005)'
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material   'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+2.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.033(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          8669
_refine_ls_number_parameters      485
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1276
_refine_ls_R_factor_gt            0.0965
_refine_ls_wR_factor_ref          0.3046
_refine_ls_wR_factor_gt           0.2894
_refine_ls_goodness_of_fit_ref    1.361
_refine_ls_restrained_S_all       1.361
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.7093(6) 0.9541(2) 0.10321(16) 0.0166(8) Uani 1 1 d . . . . .
O1 O 0.5962(5) 1.0189(2) 0.07706(13) 0.0178(7) Uani 1 1 d . . . . .
O2 O 0.8701(5) 0.8187(2) 0.14786(14) 0.0178(7) Uani 1 1 d . . . . .
O3 O 0.6299(6) 0.8214(2) 0.21462(15) 0.0239(8) Uani 1 1 d . . . . .
O4 O 1.0057(6) 1.0756(2) 0.43232(14) 0.0284(8) Uani 1 1 d . . . . .
O5 O 0.9083(5) 1.1338(2) 0.07011(13) 0.0184(7) Uani 1 1 d . . . . .
C1 C 0.8558(7) 0.9842(3) 0.14984(18) 0.0143(9) Uani 1 1 d . . . . .
C2 C 0.9273(7) 1.0837(3) 0.18214(18) 0.0152(9) Uani 1 1 d . . . . .
H2A H 1.0778 1.1110 0.1721 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7609(8) 1.1416(3) 0.15954(19) 0.0166(9) Uani 1 1 d . . . . .
H3A H 0.6224 1.1281 0.1778 0.020 Uiso 1 1 calc R U . . .
H3B H 0.8289 1.2090 0.1706 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7027(7) 1.1170(3) 0.09208(19) 0.0169(9) Uani 1 1 d . . . . .
C5 C 0.9791(8) 0.9131(3) 0.17355(19) 0.0170(9) Uani 1 1 d . . . . .
H5A H 0.9852 0.9198 0.2176 0.020 Uiso 1 1 calc R U . . .
C6 C 1.2186(8) 0.9276(3) 0.1593(2) 0.0190(9) Uani 1 1 d . . . . .
H6A H 1.2969 0.8833 0.1772 0.029 Uiso 1 1 calc R U . . .
H6B H 1.2990 0.9915 0.1755 0.029 Uiso 1 1 calc R U . . .
H6C H 1.2140 0.9174 0.1161 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6911(7) 0.7811(3) 0.17224(19) 0.0163(9) Uani 1 1 d . . . . .
C8 C 0.5765(8) 0.6836(3) 0.1399(2) 0.0224(10) Uani 1 1 d . . . . .
C9 C 0.4188(11) 0.6361(4) 0.1783(3) 0.0435(15) Uani 1 1 d . . . . .
H9A H 0.5066 0.6274 0.2152 0.065 Uiso 1 1 calc R U . . .
H9B H 0.3371 0.5751 0.1567 0.065 Uiso 1 1 calc R U . . .
H9C H 0.3111 0.6749 0.1876 0.065 Uiso 1 1 calc R U . . .
C10 C 0.7532(10) 0.6261(3) 0.1273(3) 0.0319(12) Uani 1 1 d . . . . .
H10A H 0.8415 0.6203 0.1649 0.048 Uiso 1 1 calc R U . . .
H10B H 0.8533 0.6572 0.1025 0.048 Uiso 1 1 calc R U . . .
H10C H 0.6777 0.5638 0.1066 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4440(10) 0.6976(4) 0.0814(3) 0.0367(13) Uani 1 1 d . . . . .
H11A H 0.5476 0.7311 0.0583 0.055 Uiso 1 1 calc R U . . .
H11B H 0.3306 0.7339 0.0901 0.055 Uiso 1 1 calc R U . . .
H11C H 0.3693 0.6367 0.0586 0.055 Uiso 1 1 calc R U . . .
C12 C 0.9530(7) 1.0867(3) 0.24962(18) 0.0152(9) Uani 1 1 d . . . . .
C13 C 1.1605(8) 1.1203(3) 0.28597(19) 0.0175(9) Uani 1 1 d . . . . .
H13A H 1.2876 1.1444 0.2685 0.021 Uiso 1 1 calc R U . . .
C14 C 1.1880(8) 1.1198(3) 0.3477(2) 0.0201(10) Uani 1 1 d . . . . .
H14A H 1.3308 1.1437 0.3716 0.024 Uiso 1 1 calc R U . . .
C15 C 1.0024(8) 1.0835(3) 0.37292(19) 0.0203(10) Uani 1 1 d . . . . .
C16 C 0.7935(8) 1.0498(3) 0.3380(2) 0.0215(10) Uani 1 1 d . . . . .
H16A H 0.6667 1.0259 0.3556 0.026 Uiso 1 1 calc R U . . .
C17 C 0.7698(8) 1.0510(3) 0.27697(19) 0.0187(9) Uani 1 1 d . . . . .
H17A H 0.6264 1.0272 0.2534 0.022 Uiso 1 1 calc R U . . .
C18 C 1.2193(10) 1.1081(4) 0.4703(2) 0.0329(13) Uani 1 1 d . . . . .
H18A H 1.2025 1.0974 0.5109 0.049 Uiso 1 1 calc R U . . .
H18B H 1.2713 1.1750 0.4699 0.049 Uiso 1 1 calc R U . . .
H18C H 1.3295 1.0741 0.4560 0.049 Uiso 1 1 calc R U . . .
C19 C 0.5268(8) 1.1663(3) 0.0650(2) 0.0211(10) Uani 1 1 d . . . . .
H19A H 0.4773 1.1395 0.0231 0.032 Uiso 1 1 calc R U . . .
H19B H 0.5923 1.2330 0.0680 0.032 Uiso 1 1 calc R U . . .
H19C H 0.3974 1.1582 0.0863 0.032 Uiso 1 1 calc R U . . .
C20 C 0.8901(9) 1.1126(3) 0.0065(2) 0.0243(10) Uani 1 1 d . . . . .
H20A H 1.0392 1.1104 -0.0042 0.036 Uiso 1 1 calc R U . . .
H20B H 0.8303 1.1609 -0.0121 0.036 Uiso 1 1 calc R U . . .
H20C H 0.7883 1.0519 -0.0075 0.036 Uiso 1 1 calc R U . . .
N1A N 0.0754(6) 0.5164(2) 0.39717(16) 0.0169(8) Uani 1 1 d . . . . .
O1A O -0.0675(5) 0.4510(2) 0.42356(14) 0.0202(7) Uani 1 1 d . . . . .
O2A O 0.3168(5) 0.6519(2) 0.35260(14) 0.0176(7) Uani 1 1 d . . . . .
O3A O 0.0085(5) 0.6466(2) 0.28612(14) 0.0217(7) Uani 1 1 d . . . . .
O4A O -0.0083(7) 0.3811(3) 0.07046(15) 0.0350(9) Uani 1 1 d . . . . .
O5A O 0.1589(5) 0.3404(2) 0.43475(13) 0.0189(7) Uani 1 1 d . . . . .
C1A C 0.1585(7) 0.4858(3) 0.35195(18) 0.0137(8) Uani 1 1 d . . . . .
C2A C 0.1178(7) 0.3842(3) 0.32157(19) 0.0155(9) Uani 1 1 d . . . . .
H2AA H 0.2558 0.3598 0.3336 0.019 Uiso 1 1 calc R U . . .
C3A C -0.0788(8) 0.3253(3) 0.34407(19) 0.0166(9) Uani 1 1 d . . . . .
H3AA H -0.2236 0.3355 0.3242 0.020 Uiso 1 1 calc R U . . .
H3AB H -0.0763 0.2583 0.3351 0.020 Uiso 1 1 calc R U . . .
C4A C -0.0558(8) 0.3542(3) 0.4107(2) 0.0176(9) Uani 1 1 d . . . . .
C5A C 0.3190(7) 0.5569(3) 0.32667(19) 0.0152(9) Uani 1 1 d . . . . .
H5AA H 0.2747 0.5492 0.2826 0.018 Uiso 1 1 calc R U . . .
C6A C 0.5592(8) 0.5440(3) 0.3410(2) 0.0223(10) Uani 1 1 d . . . . .
H6AA H 0.6598 0.5893 0.3234 0.033 Uiso 1 1 calc R U . . .
H6AB H 0.5681 0.4806 0.3246 0.033 Uiso 1 1 calc R U . . .
H6AC H 0.6048 0.5540 0.3842 0.033 Uiso 1 1 calc R U . . .
C7A C 0.1491(7) 0.6886(3) 0.32795(19) 0.0165(9) Uani 1 1 d . . . . .
C8A C 0.1592(8) 0.7893(3) 0.3558(2) 0.0178(9) Uani 1 1 d . . . . .
C9A C 0.2536(9) 0.8505(3) 0.3111(2) 0.0287(11) Uani 1 1 d . . . . .
H9AA H 0.4105 0.8462 0.3094 0.043 Uiso 1 1 calc R U . . .
H9AB H 0.2465 0.9156 0.3239 0.043 Uiso 1 1 calc R U . . .
H9AC H 0.1638 0.8287 0.2717 0.043 Uiso 1 1 calc R U . . .
C10A C -0.0826(9) 0.8014(3) 0.3612(2) 0.0276(11) Uani 1 1 d . . . . .
H10D H -0.1490 0.7579 0.3863 0.041 Uiso 1 1 calc R U . . .
H10E H -0.1738 0.7884 0.3216 0.041 Uiso 1 1 calc R U . . .
H10F H -0.0786 0.8656 0.3791 0.041 Uiso 1 1 calc R U . . .
C11A C 0.3108(10) 0.8163(4) 0.4160(2) 0.0320(12) Uani 1 1 d . . . . .
H11D H 0.2578 0.7733 0.4429 0.048 Uiso 1 1 calc R U . . .
H11E H 0.3063 0.8801 0.4328 0.048 Uiso 1 1 calc R U . . .
H11F H 0.4658 0.8129 0.4110 0.048 Uiso 1 1 calc R U . . .
C12A C 0.0842(8) 0.3787(3) 0.25409(19) 0.0157(9) Uani 1 1 d . . . . .
C13A C 0.2369(8) 0.3474(3) 0.2200(2) 0.0176(9) Uani 1 1 d . . . . .
H13B H 0.3601 0.3259 0.2392 0.021 Uiso 1 1 calc R U . . .
C14A C 0.2133(8) 0.3469(3) 0.1588(2) 0.0225(10) Uani 1 1 d . . . . .
H14B H 0.3202 0.3262 0.1367 0.027 Uiso 1 1 calc R U . . .
C15A C 0.0323(9) 0.3770(3) 0.1304(2) 0.0225(10) Uani 1 1 d . . . . .
C16A C -0.1249(9) 0.4068(3) 0.1634(2) 0.0226(10) Uani 1 1 d . . . . .
H16B H -0.2507 0.4261 0.1437 0.027 Uiso 1 1 calc R U . . .
C17A C -0.0986(8) 0.4085(3) 0.2246(2) 0.0201(10) Uani 1 1 d . . . . .
H17B H -0.2049 0.4300 0.2466 0.024 Uiso 1 1 calc R U . . .
C18A C 0.1619(12) 0.3610(5) 0.0365(2) 0.0450(16) Uani 1 1 d . . . . .
H18D H 0.1164 0.3671 -0.0051 0.067 Uiso 1 1 calc R U . . .
H18E H 0.1812 0.2971 0.0390 0.067 Uiso 1 1 calc R U . . .
H18F H 0.3045 0.4050 0.0522 0.067 Uiso 1 1 calc R U . . .
C19A C -0.2468(9) 0.3036(3) 0.4385(2) 0.0235(10) Uani 1 1 d . . . . .
H19D H -0.2331 0.3317 0.4801 0.035 Uiso 1 1 calc R U . . .
H19E H -0.2394 0.2376 0.4365 0.035 Uiso 1 1 calc R U . . .
H19F H -0.3914 0.3089 0.4168 0.035 Uiso 1 1 calc R U . . .
C20A C 0.2336(9) 0.3776(4) 0.4964(2) 0.0269(11) Uani 1 1 d . . . . .
H20D H 0.3875 0.3693 0.5079 0.040 Uiso 1 1 calc R U . . .
H20E H 0.1334 0.3445 0.5205 0.040 Uiso 1 1 calc R U . . .
H20F H 0.2308 0.4442 0.5027 0.040 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C1 1.279(6) . ?
N1 O1 1.429(5) . ?
O1 C4 1.450(5) . ?
O2 C7 1.350(5) . ?
O2 C5 1.443(5) . ?
O3 C7 1.215(5) . ?
O4 C15 1.381(5) . ?
O4 C18 1.438(6) . ?
O5 C4 1.405(6) . ?
O5 C20 1.442(5) . ?
C1 C5 1.517(6) . ?
C1 C2 1.519(6) . ?
C2 C3 1.531(6) . ?
C2 C12 1.531(6) . ?
C2 H2A 1.0000 . ?
C3 C4 1.526(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C19 1.521(6) . ?
C5 C6 1.524(6) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.529(6) . ?
C8 C9 1.520(7) . ?
C8 C10 1.531(7) . ?
C8 C11 1.534(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.394(6) . ?
C12 C17 1.401(6) . ?
C13 C14 1.406(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.388(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(7) . ?
C16 C17 1.392(6) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1A C1A 1.284(6) . ?
N1A O1A 1.422(5) . ?
O1A C4A 1.442(5) . ?
O2A C7A 1.344(5) . ?
O2A C5A 1.458(5) . ?
O3A C7A 1.220(5) . ?
O4A C15A 1.378(5) . ?
O4A C18A 1.432(7) . ?
O5A C4A 1.420(6) . ?
O5A C20A 1.436(5) . ?
C1A C5A 1.519(6) . ?
C1A C2A 1.535(5) . ?
C2A C12A 1.526(6) . ?
C2A C3A 1.530(6) . ?
C2A H2AA 1.0000 . ?
C3A C4A 1.518(6) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C4A C19A 1.518(6) . ?
C5A C6A 1.518(6) . ?
C5A H5AA 1.0000 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A C8A 1.532(6) . ?
C8A C11A 1.525(6) . ?
C8A C10A 1.542(7) . ?
C8A C9A 1.543(6) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A C13A 1.400(6) . ?
C12A C17A 1.405(6) . ?
C13A C14A 1.393(6) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.386(7) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.400(7) . ?
C16A C17A 1.391(6) . ?
C16A H16B 0.9500 . ?
C17A H17B 0.9500 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 N1 O1 118.6(3) . . ?
N1 O1 C4 117.2(3) . . ?
C7 O2 C5 115.3(3) . . ?
C15 O4 C18 116.6(4) . . ?
C4 O5 C20 114.9(3) . . ?
N1 C1 C5 116.1(4) . . ?
N1 C1 C2 127.2(4) . . ?
C5 C1 C2 116.7(4) . . ?
C1 C2 C3 109.6(3) . . ?
C1 C2 C12 111.5(3) . . ?
C3 C2 C12 112.3(4) . . ?
C1 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
C12 C2 H2A 107.7 . . ?
C4 C3 C2 108.9(3) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
O5 C4 O1 109.9(3) . . ?
O5 C4 C19 114.6(4) . . ?
O1 C4 C19 103.7(3) . . ?
O5 C4 C3 106.2(3) . . ?
O1 C4 C3 108.8(3) . . ?
C19 C4 C3 113.5(4) . . ?
O2 C5 C1 112.2(3) . . ?
O2 C5 C6 106.5(3) . . ?
C1 C5 C6 111.3(4) . . ?
O2 C5 H5A 108.9 . . ?
C1 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O2 123.2(4) . . ?
O3 C7 C8 124.9(4) . . ?
O2 C7 C8 111.9(4) . . ?
C9 C8 C7 108.9(4) . . ?
C9 C8 C10 110.2(4) . . ?
C7 C8 C10 110.3(4) . . ?
C9 C8 C11 110.8(5) . . ?
C7 C8 C11 106.3(4) . . ?
C10 C8 C11 110.3(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.3(4) . . ?
C13 C12 C2 121.7(4) . . ?
C17 C12 C2 121.0(4) . . ?
C12 C13 C14 122.2(4) . . ?
C12 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C13 118.7(4) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
O4 C15 C16 114.4(4) . . ?
O4 C15 C14 125.1(4) . . ?
C16 C15 C14 120.5(4) . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C12 121.4(4) . . ?
C16 C17 H17A 119.3 . . ?
C12 C17 H17A 119.3 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1A N1A O1A 118.3(3) . . ?
N1A O1A C4A 117.5(3) . . ?
C7A O2A C5A 115.6(3) . . ?
C15A O4A C18A 116.6(4) . . ?
C4A O5A C20A 115.5(3) . . ?
N1A C1A C5A 116.8(4) . . ?
N1A C1A C2A 126.9(4) . . ?
C5A C1A C2A 116.3(3) . . ?
C12A C2A C3A 113.2(4) . . ?
C12A C2A C1A 110.8(3) . . ?
C3A C2A C1A 109.6(3) . . ?
C12A C2A H2AA 107.7 . . ?
C3A C2A H2AA 107.7 . . ?
C1A C2A H2AA 107.7 . . ?
C4A C3A C2A 108.4(4) . . ?
C4A C3A H3AA 110.0 . . ?
C2A C3A H3AA 110.0 . . ?
C4A C3A H3AB 110.0 . . ?
C2A C3A H3AB 110.0 . . ?
H3AA C3A H3AB 108.4 . . ?
O5A C4A O1A 110.4(4) . . ?
O5A C4A C3A 105.7(3) . . ?
O1A C4A C3A 109.9(3) . . ?
O5A C4A C19A 113.2(4) . . ?
O1A C4A C19A 103.8(3) . . ?
C3A C4A C19A 113.8(4) . . ?
O2A C5A C6A 106.7(3) . . ?
O2A C5A C1A 111.2(3) . . ?
C6A C5A C1A 110.6(4) . . ?
O2A C5A H5AA 109.4 . . ?
C6A C5A H5AA 109.4 . . ?
C1A C5A H5AA 109.4 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
O3A C7A O2A 122.9(4) . . ?
O3A C7A C8A 123.8(4) . . ?
O2A C7A C8A 113.3(4) . . ?
C11A C8A C7A 112.6(4) . . ?
C11A C8A C10A 110.9(4) . . ?
C7A C8A C10A 108.6(4) . . ?
C11A C8A C9A 110.0(4) . . ?
C7A C8A C9A 105.4(4) . . ?
C10A C8A C9A 109.2(4) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8A C10A H10D 109.5 . . ?
C8A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C8A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C8A C11A H11D 109.5 . . ?
C8A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C8A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C13A C12A C17A 118.0(4) . . ?
C13A C12A C2A 121.7(4) . . ?
C17A C12A C2A 120.3(4) . . ?
C14A C13A C12A 121.8(4) . . ?
C14A C13A H13B 119.1 . . ?
C12A C13A H13B 119.1 . . ?
C15A C14A C13A 119.4(4) . . ?
C15A C14A H14B 120.3 . . ?
C13A C14A H14B 120.3 . . ?
O4A C15A C14A 125.1(5) . . ?
O4A C15A C16A 115.1(4) . . ?
C14A C15A C16A 119.8(4) . . ?
C17A C16A C15A 120.6(5) . . ?
C17A C16A H16B 119.7 . . ?
C15A C16A H16B 119.7 . . ?
C16A C17A C12A 120.4(4) . . ?
C16A C17A H17B 119.8 . . ?
C12A C17A H17B 119.8 . . ?
O4A C18A H18D 109.5 . . ?
O4A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
O4A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C4A C19A H19D 109.5 . . ?
C4A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C4A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
O5A C20A H20D 109.5 . . ?
O5A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
O5A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C1 N1 O1 C4 19.9(5) . . . . ?
O1 N1 C1 C5 -176.8(3) . . . . ?
O1 N1 C1 C2 0.1(7) . . . . ?
N1 C1 C2 C3 12.8(6) . . . . ?
C5 C1 C2 C3 -170.3(4) . . . . ?
N1 C1 C2 C12 137.9(5) . . . . ?
C5 C1 C2 C12 -45.3(5) . . . . ?
C1 C2 C3 C4 -42.3(5) . . . . ?
C12 C2 C3 C4 -166.8(3) . . . . ?
C20 O5 C4 O1 61.1(4) . . . . ?
C20 O5 C4 C19 -55.1(5) . . . . ?
C20 O5 C4 C3 178.7(3) . . . . ?
N1 O1 C4 O5 64.9(4) . . . . ?
N1 O1 C4 C19 -172.1(3) . . . . ?
N1 O1 C4 C3 -50.9(5) . . . . ?
C2 C3 C4 O5 -56.6(4) . . . . ?
C2 C3 C4 O1 61.6(4) . . . . ?
C2 C3 C4 C19 176.5(4) . . . . ?
C7 O2 C5 C1 -80.6(4) . . . . ?
C7 O2 C5 C6 157.4(4) . . . . ?
N1 C1 C5 O2 -14.4(5) . . . . ?
C2 C1 C5 O2 168.4(3) . . . . ?
N1 C1 C5 C6 104.8(5) . . . . ?
C2 C1 C5 C6 -72.4(5) . . . . ?
C5 O2 C7 O3 -3.3(6) . . . . ?
C5 O2 C7 C8 176.3(3) . . . . ?
O3 C7 C8 C9 -15.0(7) . . . . ?
O2 C7 C8 C9 165.5(4) . . . . ?
O3 C7 C8 C10 -136.1(5) . . . . ?
O2 C7 C8 C10 44.4(5) . . . . ?
O3 C7 C8 C11 104.3(5) . . . . ?
O2 C7 C8 C11 -75.2(5) . . . . ?
C1 C2 C12 C13 116.1(4) . . . . ?
C3 C2 C12 C13 -120.4(4) . . . . ?
C1 C2 C12 C17 -60.6(5) . . . . ?
C3 C2 C12 C17 62.9(5) . . . . ?
C17 C12 C13 C14 -0.5(6) . . . . ?
C2 C12 C13 C14 -177.3(4) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C18 O4 C15 C16 179.0(4) . . . . ?
C18 O4 C15 C14 0.2(7) . . . . ?
C13 C14 C15 O4 177.7(4) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
O4 C15 C16 C17 -177.9(4) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C12 -0.6(7) . . . . ?
C13 C12 C17 C16 0.4(6) . . . . ?
C2 C12 C17 C16 177.2(4) . . . . ?
C1A N1A O1A C4A 18.8(5) . . . . ?
O1A N1A C1A C5A -177.2(3) . . . . ?
O1A N1A C1A C2A 0.9(6) . . . . ?
N1A C1A C2A C12A 138.1(5) . . . . ?
C5A C1A C2A C12A -43.7(5) . . . . ?
N1A C1A C2A C3A 12.5(6) . . . . ?
C5A C1A C2A C3A -169.3(4) . . . . ?
C12A C2A C3A C4A -166.2(4) . . . . ?
C1A C2A C3A C4A -42.0(5) . . . . ?
C20A O5A C4A O1A 51.4(5) . . . . ?
C20A O5A C4A C3A 170.2(4) . . . . ?
C20A O5A C4A C19A -64.6(5) . . . . ?
N1A O1A C4A O5A 65.4(4) . . . . ?
N1A O1A C4A C3A -50.8(5) . . . . ?
N1A O1A C4A C19A -172.9(3) . . . . ?
C2A C3A C4A O5A -57.5(4) . . . . ?
C2A C3A C4A O1A 61.7(5) . . . . ?
C2A C3A C4A C19A 177.6(4) . . . . ?
C7A O2A C5A C6A 156.8(4) . . . . ?
C7A O2A C5A C1A -82.6(4) . . . . ?
N1A C1A C5A O2A -10.7(5) . . . . ?
C2A C1A C5A O2A 171.0(3) . . . . ?
N1A C1A C5A C6A 107.7(4) . . . . ?
C2A C1A C5A C6A -70.6(5) . . . . ?
C5A O2A C7A O3A -1.0(6) . . . . ?
C5A O2A C7A C8A -178.4(3) . . . . ?
O3A C7A C8A C11A 165.7(5) . . . . ?
O2A C7A C8A C11A -17.0(6) . . . . ?
O3A C7A C8A C10A 42.5(6) . . . . ?
O2A C7A C8A C10A -140.2(4) . . . . ?
O3A C7A C8A C9A -74.4(6) . . . . ?
O2A C7A C8A C9A 103.0(4) . . . . ?
C3A C2A C12A C13A -121.3(4) . . . . ?
C1A C2A C12A C13A 115.1(4) . . . . ?
C3A C2A C12A C17A 61.0(5) . . . . ?
C1A C2A C12A C17A -62.5(5) . . . . ?
C17A C12A C13A C14A 1.1(6) . . . . ?
C2A C12A C13A C14A -176.6(4) . . . . ?
C12A C13A C14A C15A -0.9(7) . . . . ?
C18A O4A C15A C14A -6.2(7) . . . . ?
C18A O4A C15A C16A 173.3(4) . . . . ?
C13A C14A C15A O4A 179.1(4) . . . . ?
C13A C14A C15A C16A -0.4(7) . . . . ?
O4A C15A C16A C17A -178.1(4) . . . . ?
C14A C15A C16A C17A 1.4(7) . . . . ?
C15A C16A C17A C12A -1.2(7) . . . . ?
C13A C12A C17A C16A -0.1(6) . . . . ?
C2A C12A C17A C16A 177.6(4) . . . . ?
 
_refine_diff_density_max    0.567
_refine_diff_density_min   -0.593
_refine_diff_density_rms    0.120

_shelxl_version_number 2014/6



