# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_moon186_072113_0m_a
_database_code_depnum_ccdc_archive 'CCDC 964594'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C H Cl3, C29 H49 N5 O8'
_chemical_formula_sum            'C30 H50 Cl3 N5 O8'
_chemical_formula_weight         715.10
_chemical_absolute_configuration rm
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2919(4)
_cell_length_b                   11.0410(5)
_cell_length_c                   19.2470(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.1200(16)
_cell_angle_gamma                90
_cell_volume                     1943.87(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9536
_cell_measurement_temperature    304
_cell_measurement_theta_max      23.21
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0633 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8822.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      304.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4951
_reflns_number_total             7676
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         7676
_refine_ls_number_restraints     122
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.013
_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)+(0.1095P)²+0.4898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1975
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5(0.072) H12(0.061) H15(0.061) H22(0.069) H25(0.067) H1A(0.166)
 H1B(0.166) H1C(0.166) H7(0.081) H8AA(0.132) H8AB(0.132) H8BC(0.132)
 H8BD(0.132) H9A(0.114) H9B(0.114) H10A(0.093) H10B(0.093) H10C(0.093)
 H10D(0.093) H11(0.063) H14(0.065) H17(0.076) H18A(0.138) H18B(0.138)
 H18C(0.138) H18D(0.138) H19A(0.153) H19B(0.153) H20A(0.118) H20B(0.118)
 H20C(0.118) H20D(0.118) H21(0.074) H29A(0.151) H29B(0.151) H29C(0.151)
 H30A(0.227) H30B(0.227) H30C(0.227) H31A(0.2) H31B(0.2) H31C(0.2) H33A(0.142)
 H33B(0.142) H33C(0.142) H34A(0.12) H34B(0.12) H34C(0.12) H37A(0.137)
 H37B(0.137) H37C(0.137) H40A(0.129) H40B(0.129) H40C(0.129) H41A(0.11)
 H41B(0.11) H41C(0.11) H49A(0.112) H49B(0.112) H50A(0.141) H50B(0.141)
 H51(0.148)
 Fixed X: H5(0.2315) H12(0.244) H15(0.0767) H22(-0.2557) H25(-0.3365)
 H1A(0.3263) H1B(0.2893) H1C(0.4493) H7(0.2413) H8AA(0.4613) H8AB(0.3075)
 H8BC(0.3408) H8BD(0.4972) H9A(0.4334) H9B(0.5703) H10A(0.4816) H10B(0.3182)
 H10C(0.3566) H10D(0.5141) H11(0.5157) H14(0.3188) H17(-0.1264) H18A(-0.0656)
 H18B(-0.2255) H18C(-0.1489) H18D(-0.0756) H19A(-0.2438) H19B(-0.0821) H20A(-
 0.2272) H20B(-0.3193) H20C(-0.3054) H20D(-0.1805) H21(-0.0228) H29A(-0.1758)
 H29B(-0.1542) H29C(-0.0689) H30A(-0.5073) H30B(-0.4414) H30C(-0.4308) H31A(-
 0.1728) H31B(-0.246) H31C(-0.3418) H33A(0.434) H33B(0.4916) H33C(0.5533)
 H34A(0.1337) H34B(0.2289) H34C(0.179) H37A(0.2518) H37B(0.4093) H37C(0.2743)
 H40A(0.0298) H40B(0.0166) H40C(-0.0855) H41A(-0.2894) H41B(-0.1848) H41C(-
 0.3193) H49A(0.3808) H49B(0.2406) H50A(-0.3173) H50B(-0.3372) H51(0.765)
 Fixed Y: H5(0.9814) H12(1.2829) H15(1.3654) H22(1.2937) H25(1.5392)
 H1A(0.5424) H1B(0.6152) H1C(0.615) H7(1.0991) H8AA(1.0293) H8AB(1.083)
 H8BC(1.0332) H8BD(1.0842) H9A(1.2499) H9B(1.2118) H10A(1.3639) H10B(1.3271)
 H10C(1.3681) H10D(1.32) H11(1.1999) H14(1.2953) H17(1.2484) H18A(1.0267)
 H18B(1.0811) H18C(1.0752) H18D(0.9934) H19A(0.9177) H19B(0.9385) H20A(1.0305)
 H20B(1.0947) H20C(1.0877) H20D(0.9906) H21(1.1398) H29A(1.7616) H29B(1.7036)
 H29C(1.6519) H30A(1.6142) H30B(1.6431) H30C(1.739) H31A(1.4414) H31B(1.4898)
 H31C(1.4272) H33A(0.9408) H33B(0.8071) H33C(0.9022) H34A(0.7877) H34B(0.7316)
 H34C(0.8673) H37A(1.4963) H37B(1.4876) H37C(1.5099) H40A(1.5867) H40B(1.5574)
 H40C(1.6551) H41A(1.5318) H41B(1.426) H41C(1.3996) H49A(1.2347) H49B(1.217)
 H50A(0.9762) H50B(1.1183) H51(0.9441)
 Fixed Z: H5(0.2567) H12(0.2749) H15(0.1516) H22(0.2359) H25(0.2346)
 H1A(0.3397) H1B(0.4043) H1C(0.3887) H7(0.351) H8AA(0.459) H8AB(0.4663)
 H8BC(0.4661) H8BD(0.4591) H9A(0.5073) H9B(0.474) H10A(0.4048) H10B(0.4068)
 H10C(0.3933) H10D(0.4262) H11(0.3353) H14(0.1123) H17(0.1211) H18A(0.079)
 H18B(0.0702) H18C(0.053) H18D(0.1172) H19A(0.1519) H19B(0.1922) H20A(0.2597)
 H20B(0.193) H20C(0.2358) H20D(0.2346) H21(0.252) H29A(0.0689) H29B(-0.0029)
 H29C(0.0684) H30A(0.032) H30B(-0.0357) H30C(0.025) H31A(0.0434) H31B(-0.031)
 H31C(0.0181) H33A(0.1555) H33B(0.1617) H33C(0.2198) H34A(0.2048) H34B(0.1533)
 H34C(0.1447) H37A(0.1023) H37B(0.1475) H37C(0.1846) H40A(0.2891) H40B(0.3674)
 H40C(0.325) H41A(0.3632) H41B(0.3941) H41C(0.3345) H49A(0.5057) H49B(0.4471)
 H50A(0.1125) H50B(0.1069) H51(0.388)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl52 Cl 1.0019(4) 0.9066(4) 0.3743(2) 0.1719(13) Uani 1 1 d . U . . .
Cl53 Cl 0.8856(7) 1.1201(4) 0.4225(3) 0.231(2) Uani 1 1 d . U . . .
Cl54 Cl 0.8724(5) 0.9019(6) 0.4975(2) 0.226(2) Uani 1 1 d . U . . .
O2 O 0.3149(4) 0.7176(4) 0.3244(3) 0.0754(12) Uani 1 1 d . U . . .
O27 O -0.3051(4) 1.5851(5) 0.1228(2) 0.0805(13) Uani 1 1 d . U . . .
O32 O 0.4961(5) 0.6684(5) 0.2689(3) 0.0953(15) Uani 1 1 d . U . . .
O35 O 0.5172(5) 0.9341(4) 0.3507(3) 0.0911(15) Uani 1 1 d . U . . .
O36 O 0.5197(4) 1.2683(5) 0.2148(3) 0.0843(14) Uani 1 1 d . U . . .
O38 O 0.1688(4) 1.1061(3) 0.1466(2) 0.0615(10) Uani 1 1 d . U . . .
O39 O 0.0534(3) 1.3443(4) 0.3051(2) 0.0669(10) Uani 1 1 d . U . . .
O42 O -0.0810(4) 1.5033(4) 0.1600(2) 0.0647(10) Uani 1 1 d . U . . .
N5 N 0.3137(5) 0.9452(4) 0.2699(3) 0.0603(11) Uani 1 1 d . U . . .
H5 H 0.2315 0.9814 0.2567 0.072 Uiso 1 1 calc R . . . .
N12 N 0.3345(4) 1.2651(4) 0.2762(2) 0.0510(10) Uani 1 1 d . U . . .
H12 H 0.2440 1.2829 0.2749 0.061 Uiso 1 1 calc R . . . .
N15 N 0.1372(4) 1.3067(4) 0.1507(2) 0.0505(10) Uani 1 1 d . U . . .
H15 H 0.0767 1.3654 0.1516 0.061 Uiso 1 1 calc R . . . .
N22 N -0.1633(4) 1.2793(4) 0.2452(3) 0.0572(11) Uani 1 1 d . U . . .
H22 H -0.2557 1.2937 0.2359 0.069 Uiso 1 1 calc R . . . .
N25 N -0.2470(5) 1.5224(4) 0.2325(2) 0.0558(11) Uani 1 1 d . U . . .
H25 H -0.3365 1.5392 0.2346 0.067 Uiso 1 1 calc R . . . .
C1 C 0.3476(10) 0.6143(8) 0.3678(5) 0.111(3) Uani 1 1 d . U . . .
H1A H 0.3263 0.5424 0.3397 0.166 Uiso 1 1 calc GR . . . .
H1B H 0.2893 0.6152 0.4043 0.166 Uiso 1 1 calc GR . . . .
H1C H 0.4493 0.6150 0.3887 0.166 Uiso 1 1 calc GR . . . .
C3 C 0.4000(6) 0.7353(5) 0.2760(4) 0.0642(14) Uani 1 1 d . U . . .
C4 C 0.3501(6) 0.8429(5) 0.2285(3) 0.0614(13) Uani 1 1 d . U . . .
C6 C 0.4025(6) 0.9851(5) 0.3272(4) 0.0664(15) Uani 1 1 d . U . . .
C7 C 0.3481(7) 1.0950(6) 0.3634(3) 0.0675(14) Uani 1 1 d . U . . .
H7 H 0.2413 1.0991 0.3510 0.081 Uiso 1 1 calc R . . . .
C8 C 0.3927(12) 1.0944(8) 0.4442(4) 0.110(3) Uani 1 1 d . U . . .
H8AA H 0.4613 1.0293 0.4590 0.132 Uiso 0.80(3) 1 calc R . P A 1
H8AB H 0.3075 1.0830 0.4663 0.132 Uiso 0.80(3) 1 calc R . P A 1
H8BC H 0.3408 1.0332 0.4661 0.132 Uiso 0.20(3) 1 calc R . P A 2
H8BD H 0.4972 1.0842 0.4591 0.132 Uiso 0.20(3) 1 calc R . P A 2
C9 C 0.4646(19) 1.2186(10) 0.4652(5) 0.095(4) Uani 0.80(3) 1 d . U P A 1
H9A H 0.4334 1.2499 0.5073 0.114 Uiso 0.80(3) 1 calc R . P A 1
H9B H 0.5703 1.2118 0.4740 0.114 Uiso 0.80(3) 1 calc R . P A 1
C10 C 0.4154(8) 1.2961(6) 0.4055(3) 0.0774(17) Uani 1 1 d . U . . .
H10A H 0.4816 1.3639 0.4048 0.093 Uiso 0.80(3) 1 calc R . P A 1
H10B H 0.3182 1.3271 0.4068 0.093 Uiso 0.80(3) 1 calc R . P A 1
H10C H 0.3566 1.3681 0.3933 0.093 Uiso 0.20(3) 1 calc R . P A 2
H10D H 0.5141 1.3200 0.4262 0.093 Uiso 0.20(3) 1 calc R . P A 2
C11 C 0.4145(5) 1.2149(5) 0.3411(3) 0.0529(12) Uani 1 1 d . U . . .
H11 H 0.5157 1.1999 0.3353 0.063 Uiso 1 1 calc R . . . .
C13 C 0.3907(5) 1.2856(5) 0.2187(3) 0.0522(12) Uani 1 1 d . U . . .
C14 C 0.2892(5) 1.3334(5) 0.1535(3) 0.0544(12) Uani 1 1 d . U . . .
H14 H 0.3188 1.2953 0.1123 0.065 Uiso 1 1 calc R . . . .
C16 C 0.0867(5) 1.1916(5) 0.1465(3) 0.0501(12) Uani 1 1 d . U . . .
C17 C -0.0760(5) 1.1771(6) 0.1440(3) 0.0636(14) Uani 1 1 d . U . . .
H17 H -0.1264 1.2484 0.1211 0.076 Uiso 1 1 calc R . . . .
C18 C -0.1370(8) 1.0636(9) 0.1036(5) 0.115(3) Uani 1 1 d . U . . .
H18A H -0.0656 1.0267 0.0790 0.138 Uiso 0.67(2) 1 calc R . P B 1
H18B H -0.2255 1.0811 0.0702 0.138 Uiso 0.67(2) 1 calc R . P B 1
H18C H -0.1489 1.0752 0.0530 0.138 Uiso 0.33(2) 1 calc R . P B 2
H18D H -0.0756 0.9934 0.1172 0.138 Uiso 0.33(2) 1 calc R . P B 2
C19 C -0.1702(18) 0.9783(13) 0.1684(11) 0.127(7) Uani 0.67(2) 1 d . U P B 1
H19A H -0.2438 0.9177 0.1519 0.153 Uiso 0.67(2) 1 calc R . P B 1
H19B H -0.0821 0.9385 0.1922 0.153 Uiso 0.67(2) 1 calc R . P B 1
C20 C -0.2230(9) 1.0654(6) 0.2138(5) 0.098(2) Uani 1 1 d . U . . .
H20A H -0.2272 1.0305 0.2597 0.118 Uiso 0.67(2) 1 calc R . P B 1
H20B H -0.3193 1.0947 0.1930 0.118 Uiso 0.67(2) 1 calc R . P B 1
H20C H -0.3054 1.0877 0.2358 0.118 Uiso 0.33(2) 1 calc R . P B 2
H20D H -0.1805 0.9906 0.2346 0.118 Uiso 0.33(2) 1 calc R . P B 2
C21 C -0.1112(5) 1.1654(5) 0.2198(4) 0.0616(14) Uani 1 1 d . U . . .
H21 H -0.0228 1.1398 0.2520 0.074 Uiso 1 1 calc R . . . .
C23 C -0.0772(5) 1.3621(5) 0.2817(3) 0.0522(12) Uani 1 1 d . U . . .
C24 C -0.1497(5) 1.4813(5) 0.2961(3) 0.0517(12) Uani 1 1 d . U . . .
C26 C -0.1999(6) 1.5344(5) 0.1712(3) 0.0567(13) Uani 1 1 d . U . . .
C28 C -0.2836(7) 1.6003(8) 0.0494(3) 0.0849(18) Uani 1 1 d . U . . .
C29 C -0.1592(10) 1.6873(8) 0.0456(4) 0.101(2) Uani 1 1 d . U . . .
H29A H -0.1758 1.7616 0.0689 0.151 Uiso 1 1 calc GR . . . .
H29B H -0.1542 1.7036 -0.0029 0.151 Uiso 1 1 calc GR . . . .
H29C H -0.0689 1.6519 0.0684 0.151 Uiso 1 1 calc GR . . . .
C30 C -0.4292(10) 1.6541(14) 0.0145(5) 0.152(5) Uani 1 1 d . U . . .
H30A H -0.5073 1.6142 0.0320 0.227 Uiso 1 1 calc GR . . . .
H30B H -0.4414 1.6431 -0.0357 0.227 Uiso 1 1 calc GR . . . .
H30C H -0.4308 1.7390 0.0250 0.227 Uiso 1 1 calc GR . . . .
C31 C -0.2588(14) 1.4785(10) 0.0170(5) 0.133(3) Uani 1 1 d . U . . .
H31A H -0.1728 1.4414 0.0434 0.200 Uiso 1 1 calc GR . . . .
H31B H -0.2460 1.4898 -0.0310 0.200 Uiso 1 1 calc GR . . . .
H31C H -0.3418 1.4272 0.0181 0.200 Uiso 1 1 calc GR . . . .
C33 C 0.4679(9) 0.8763(7) 0.1877(5) 0.095(2) Uani 1 1 d . U . . .
H33A H 0.4340 0.9408 0.1555 0.142 Uiso 1 1 calc GR . . . .
H33B H 0.4916 0.8071 0.1617 0.142 Uiso 1 1 calc GR . . . .
H33C H 0.5533 0.9022 0.2198 0.142 Uiso 1 1 calc GR . . . .
C34 C 0.2096(7) 0.8037(6) 0.1781(4) 0.0798(18) Uani 1 1 d . U . . .
H34A H 0.1337 0.7877 0.2048 0.120 Uiso 1 1 calc GR . . . .
H34B H 0.2289 0.7316 0.1533 0.120 Uiso 1 1 calc GR . . . .
H34C H 0.1790 0.8673 0.1447 0.120 Uiso 1 1 calc GR . . . .
C37 C 0.3079(8) 1.4693(7) 0.1463(5) 0.091(2) Uani 1 1 d . U . . .
H37A H 0.2518 1.4963 0.1023 0.137 Uiso 1 1 calc GR . . . .
H37B H 0.4093 1.4876 0.1475 0.137 Uiso 1 1 calc GR . . . .
H37C H 0.2743 1.5099 0.1846 0.137 Uiso 1 1 calc GR . . . .
C40 C -0.0367(8) 1.5793(7) 0.3218(4) 0.0857(19) Uani 1 1 d . U . . .
H40A H 0.0298 1.5867 0.2891 0.129 Uiso 1 1 calc GR . . . .
H40B H 0.0166 1.5574 0.3674 0.129 Uiso 1 1 calc GR . . . .
H40C H -0.0855 1.6551 0.3250 0.129 Uiso 1 1 calc GR . . . .
C41 C -0.2447(7) 1.4574(7) 0.3522(3) 0.0737(17) Uani 1 1 d . U . . .
H41A H -0.2894 1.5318 0.3632 0.110 Uiso 1 1 calc GR . . . .
H41B H -0.1848 1.4260 0.3941 0.110 Uiso 1 1 calc GR . . . .
H41C H -0.3193 1.3996 0.3345 0.110 Uiso 1 1 calc GR . . . .
C49 C 0.346(7) 1.212(4) 0.457(2) 0.093(12) Uani 0.20(3) 1 d . U P A 2
H49A H 0.3808 1.2347 0.5057 0.112 Uiso 0.20(3) 1 calc R . P A 2
H49B H 0.2406 1.2170 0.4471 0.112 Uiso 0.20(3) 1 calc R . P A 2
C50 C -0.271(3) 1.054(4) 0.1259(17) 0.118(12) Uani 0.33(2) 1 d . U P B 2
H50A H -0.3173 0.9762 0.1125 0.141 Uiso 0.33(2) 1 calc R . P B 2
H50B H -0.3372 1.1183 0.1069 0.141 Uiso 0.33(2) 1 calc R . P B 2
C51 C 0.8605(11) 0.9627(11) 0.4165(6) 0.123(3) Uani 1 1 d . U . . .
H51 H 0.7650 0.9441 0.3880 0.148 Uiso 1 1 calc R . . . .


_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
Cl52 C51 1.774(11) . ?
Cl53 C51 1.754(13) . ?
Cl54 C51 1.683(11) . ?
O2 C1 1.415(9) . ?
O2 C3 1.338(8) . ?
O27 C26 1.349(7) . ?
O27 C28 1.471(8) . ?
O32 C3 1.184(7) . ?
O35 C6 1.220(7) . ?
O36 C13 1.229(6) . ?
O38 C16 1.214(6) . ?
O39 C23 1.234(6) . ?
O42 C26 1.213(6) . ?
N5 C4 1.455(7) . ?
N5 C6 1.331(8) . ?
N12 C11 1.447(7) . ?
N12 C13 1.323(7) . ?
N15 C14 1.434(6) . ?
N15 C16 1.353(7) . ?
N22 C21 1.462(7) . ?
N22 C23 1.331(7) . ?
N25 C24 1.460(7) . ?
N25 C26 1.335(7) . ?
C3 C4 1.521(9) . ?
C4 C33 1.501(9) . ?
C4 C34 1.546(8) . ?
C6 C7 1.529(9) . ?
C7 C8 1.537(10) . ?
C7 C11 1.553(8) . ?
C8 C9 1.548(16) . ?
C8 C49 1.40(4) . ?
C9 C10 1.442(12) . ?
C10 C11 1.529(8) . ?
C10 C49 1.58(4) . ?
C13 C14 1.524(8) . ?
C14 C37 1.521(9) . ?
C16 C17 1.513(7) . ?
C17 C18 1.529(10) . ?
C17 C21 1.555(9) . ?
C18 C19 1.63(2) . ?
C18 C50 1.39(3) . ?
C19 C20 1.442(14) . ?
C20 C21 1.507(9) . ?
C20 C50 1.68(3) . ?
C23 C24 1.526(8) . ?
C24 C40 1.528(8) . ?
C24 C41 1.533(8) . ?
C28 C29 1.514(11) . ?
C28 C30 1.522(11) . ?
C28 C31 1.517(14) . ?

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 O2 C1 115.9(6) . . ?
C26 O27 C28 120.5(5) . . ?
C6 N5 C4 122.7(5) . . ?
C13 N12 C11 124.7(4) . . ?
C16 N15 C14 121.6(4) . . ?
C23 N22 C21 124.3(4) . . ?
C26 N25 C24 121.4(4) . . ?
O2 C3 C4 112.1(5) . . ?
O32 C3 O2 122.6(6) . . ?
O32 C3 C4 125.1(6) . . ?
N5 C4 C3 110.7(5) . . ?
N5 C4 C33 110.9(5) . . ?
N5 C4 C34 108.1(5) . . ?
C3 C4 C34 107.0(5) . . ?
C33 C4 C3 109.4(5) . . ?
C33 C4 C34 110.6(6) . . ?
O35 C6 N5 121.8(6) . . ?
O35 C6 C7 122.4(6) . . ?
N5 C6 C7 115.7(5) . . ?
C6 C7 C8 113.9(6) . . ?
C6 C7 C11 111.8(5) . . ?
C8 C7 C11 103.5(6) . . ?
C7 C8 C9 106.7(7) . . ?
C49 C8 C7 98(2) . . ?
C10 C9 C8 104.8(8) . . ?
C9 C10 C11 104.7(6) . . ?
C11 C10 C49 102.6(15) . . ?
N12 C11 C7 113.4(4) . . ?
N12 C11 C10 113.8(4) . . ?
C10 C11 C7 102.8(5) . . ?
O36 C13 N12 123.8(5) . . ?
O36 C13 C14 118.3(5) . . ?
N12 C13 C14 118.0(4) . . ?
N15 C14 C13 115.0(4) . . ?
N15 C14 C37 109.1(5) . . ?
C37 C14 C13 110.6(5) . . ?
O38 C16 N15 121.3(4) . . ?
O38 C16 C17 122.8(5) . . ?
N15 C16 C17 115.8(4) . . ?
C16 C17 C18 112.5(5) . . ?
C16 C17 C21 110.6(5) . . ?
C18 C17 C21 106.8(6) . . ?
C17 C18 C19 100.8(8) . . ?
C50 C18 C17 100.4(14) . . ?
C20 C19 C18 102.1(11) . . ?
C19 C20 C21 103.4(7) . . ?
C21 C20 C50 101.1(11) . . ?
N22 C21 C17 112.3(5) . . ?
N22 C21 C20 113.0(4) . . ?
C20 C21 C17 104.2(5) . . ?
O39 C23 N22 123.0(5) . . ?
O39 C23 C24 120.5(5) . . ?
N22 C23 C24 116.4(4) . . ?
N25 C24 C23 110.1(4) . . ?
N25 C24 C40 109.9(5) . . ?
N25 C24 C41 107.2(4) . . ?
C23 C24 C40 111.7(4) . . ?
C23 C24 C41 107.9(5) . . ?
C40 C24 C41 110.0(5) . . ?
O42 C26 O27 124.5(5) . . ?
O42 C26 N25 125.5(5) . . ?
N25 C26 O27 110.0(4) . . ?
O27 C28 C29 110.6(6) . . ?
O27 C28 C30 102.0(6) . . ?
O27 C28 C31 110.5(7) . . ?
C29 C28 C30 111.0(8) . . ?
C29 C28 C31 111.7(7) . . ?
C31 C28 C30 110.6(9) . . ?
C8 C49 C10 105(3) . . ?
C18 C50 C20 102.1(17) . . ?
Cl53 C51 Cl52 106.0(6) . . ?
Cl54 C51 Cl52 110.6(7) . . ?
Cl54 C51 Cl53 110.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 N5 44.0(6) . . . . ?
O2 C3 C4 C33 166.5(5) . . . . ?
O2 C3 C4 C34 -73.6(6) . . . . ?
O32 C3 C4 N5 -141.0(6) . . . . ?
O32 C3 C4 C33 -18.5(8) . . . . ?
O32 C3 C4 C34 101.4(7) . . . . ?
O35 C6 C7 C8 -31.8(9) . . . . ?
O35 C6 C7 C11 85.2(7) . . . . ?
O36 C13 C14 N15 156.2(5) . . . . ?
O36 C13 C14 C37 -79.7(7) . . . . ?
O38 C16 C17 C18 -30.7(9) . . . . ?
O38 C16 C17 C21 88.6(6) . . . . ?
O39 C23 C24 N25 138.4(5) . . . . ?
O39 C23 C24 C40 16.0(7) . . . . ?
O39 C23 C24 C41 -104.9(5) . . . . ?
N5 C6 C7 C8 145.5(7) . . . . ?
N5 C6 C7 C11 -97.6(6) . . . . ?
N12 C13 C14 N15 -23.8(7) . . . . ?
N12 C13 C14 C37 100.3(6) . . . . ?
N15 C16 C17 C18 150.9(6) . . . . ?
N15 C16 C17 C21 -89.8(6) . . . . ?
N22 C23 C24 N25 -43.7(6) . . . . ?
N22 C23 C24 C40 -166.1(5) . . . . ?
N22 C23 C24 C41 73.0(6) . . . . ?
C1 O2 C3 O32 0.7(9) . . . . ?
C1 O2 C3 C4 175.9(6) . . . . ?
C4 N5 C6 O35 -3.8(9) . . . . ?
C4 N5 C6 C7 178.9(5) . . . . ?
C6 N5 C4 C3 49.6(7) . . . . ?
C6 N5 C4 C33 -72.0(7) . . . . ?
C6 N5 C4 C34 166.6(6) . . . . ?
C6 C7 C8 C9 128.4(9) . . . . ?
C6 C7 C8 C49 171(2) . . . . ?
C6 C7 C11 N12 84.9(6) . . . . ?
C6 C7 C11 C10 -151.8(5) . . . . ?
C7 C8 C9 C10 19.3(13) . . . . ?
C7 C8 C49 C10 -50(3) . . . . ?
C8 C7 C11 N12 -152.1(6) . . . . ?
C8 C7 C11 C10 -28.7(6) . . . . ?
C8 C9 C10 C11 -38.0(12) . . . . ?
C8 C9 C10 C49 55(2) . . . . ?
C9 C8 C49 C10 56(2) . . . . ?
C9 C10 C11 N12 165.4(8) . . . . ?
C9 C10 C11 C7 42.3(9) . . . . ?
C9 C10 C49 C8 -65(3) . . . . ?
C11 N12 C13 O36 -2.9(8) . . . . ?
C11 N12 C13 C14 177.1(5) . . . . ?
C11 C7 C8 C9 6.7(10) . . . . ?
C11 C7 C8 C49 50(2) . . . . ?
C11 C10 C49 C8 33(4) . . . . ?
C13 N12 C11 C7 -120.7(5) . . . . ?
C13 N12 C11 C10 122.2(6) . . . . ?
C14 N15 C16 O38 1.6(7) . . . . ?
C14 N15 C16 C17 179.9(5) . . . . ?
C16 N15 C14 C13 -63.8(6) . . . . ?
C16 N15 C14 C37 171.2(6) . . . . ?
C16 C17 C18 C19 108.4(8) . . . . ?
C16 C17 C18 C50 164.0(18) . . . . ?
C16 C17 C21 N22 100.1(5) . . . . ?
C16 C17 C21 C20 -137.2(5) . . . . ?
C17 C18 C19 C20 37.9(12) . . . . ?
C17 C18 C50 C20 -50(2) . . . . ?
C18 C17 C21 N22 -137.2(6) . . . . ?
C18 C17 C21 C20 -14.5(7) . . . . ?
C18 C19 C20 C21 -48.3(13) . . . . ?
C18 C19 C20 C50 45.6(13) . . . . ?
C19 C18 C50 C20 46.3(14) . . . . ?
C19 C20 C21 N22 162.4(11) . . . . ?
C19 C20 C21 C17 40.2(12) . . . . ?
C19 C20 C50 C18 -56.9(18) . . . . ?
C21 N22 C23 O39 -9.1(8) . . . . ?
C21 N22 C23 C24 173.1(5) . . . . ?
C21 C17 C18 C19 -13.1(9) . . . . ?
C21 C17 C18 C50 42.5(19) . . . . ?
C21 C20 C50 C18 42(2) . . . . ?
C23 N22 C21 C17 -91.4(6) . . . . ?
C23 N22 C21 C20 151.0(6) . . . . ?
C24 N25 C26 O27 -173.7(5) . . . . ?
C24 N25 C26 O42 7.1(9) . . . . ?
C26 O27 C28 C29 -64.4(9) . . . . ?
C26 O27 C28 C30 177.5(8) . . . . ?
C26 O27 C28 C31 59.9(9) . . . . ?
C26 N25 C24 C23 -53.5(6) . . . . ?
C26 N25 C24 C40 70.0(6) . . . . ?
C26 N25 C24 C41 -170.5(5) . . . . ?
C28 O27 C26 O42 3.4(9) . . . . ?
C28 O27 C26 N25 -175.8(6) . . . . ?
C49 C8 C9 C10 -64(3) . . . . ?
C49 C10 C11 N12 122(2) . . . . ?
C49 C10 C11 C7 -1(2) . . . . ?
C50 C18 C19 C20 -57.2(16) . . . . ?
C50 C20 C21 N22 108.3(15) . . . . ?
C50 C20 C21 C17 -13.9(15) . . . . ?

####################################################################### 
# 
# 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_cu_moon180_062513_0m
_database_code_depnum_ccdc_archive 'CCDC 964598'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-02-06
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H44 N4 O9'
_chemical_formula_sum            'C27 H44 N4 O9'
_chemical_formula_weight         568.66
_chemical_absolute_configuration rm
_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'

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

_cell_length_a                   10.4185(4)
_cell_length_b                   15.6536(6)
_cell_length_c                   18.1560(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2961.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.05
_cell_measurement_theta_min      4.89
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.9270.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25847
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.046
_diffrn_reflns_theta_min         3.728
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                5114
_reflns_number_total             5656
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.00087(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.057
_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)+(0.0445P)²+0.4167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C11(H11), C14(H14), C17(H17), C21(H21), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N12(H12), N22(H22), N25(H25)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.12724(17) 0.71743(11) 0.32168(11) 0.0343(4) Uani 1 1 d . . . . .
O15 O 0.57763(15) 0.46482(10) 0.23979(9) 0.0240(4) Uani 1 1 d . . . . .
O27 O 0.32153(15) 0.19960(10) 0.16963(9) 0.0237(4) Uani 1 1 d . . . . .
O32 O -0.04467(17) 0.74752(11) 0.38931(12) 0.0361(5) Uani 1 1 d . . . . .
O34 O -0.04228(16) 0.60950(11) 0.20196(10) 0.0289(4) Uani 1 1 d . . . . .
O35 O 0.48236(16) 0.66301(11) 0.16260(11) 0.0320(4) Uani 1 1 d . . . . .
O37 O 0.76201(17) 0.47992(11) 0.30134(11) 0.0352(5) Uani 1 1 d . . . . .
O38 O 0.27776(15) 0.45282(10) 0.35296(10) 0.0256(4) Uani 1 1 d . . . . .
O40 O 0.32539(16) 0.34311(10) 0.19126(10) 0.0266(4) Uani 1 1 d . . . . .
N5 N 0.06218(18) 0.55470(12) 0.30006(11) 0.0229(4) Uani 1 1 d . . . . .
H5 H 0.1220 0.5194 0.3158 0.028 Uiso 1 1 calc R U . . .
N12 N 0.37334(18) 0.53992(12) 0.18055(11) 0.0224(4) Uani 1 1 d . . . . .
H12 H 0.3766 0.4860 0.1940 0.027 Uiso 1 1 calc R U . . .
N22 N 0.39746(17) 0.33197(12) 0.36003(11) 0.0208(4) Uani 1 1 d . . . . .
H22 H 0.3958 0.2759 0.3565 0.025 Uiso 1 1 calc R U . . .
N25 N 0.22186(18) 0.25194(12) 0.26807(11) 0.0206(4) Uani 1 1 d . . . . .
H25 H 0.2032 0.1986 0.2791 0.025 Uiso 1 1 calc R U . . .
C1 C 0.1585(3) 0.80776(16) 0.32422(18) 0.0386(7) Uani 1 1 d . . . . .
H1A H 0.0958 0.8399 0.2951 0.058 Uiso 1 1 calc R U . . .
H1B H 0.2446 0.8168 0.3039 0.058 Uiso 1 1 calc R U . . .
H1C H 0.1563 0.8276 0.3754 0.058 Uiso 1 1 calc R U . . .
C3 C 0.0197(2) 0.69663(16) 0.35677(14) 0.0236(5) Uani 1 1 d . . . . .
C4 C -0.0137(2) 0.60189(15) 0.35312(14) 0.0248(5) Uani 1 1 d . . . . .
H4 H -0.1057 0.5972 0.3380 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0430(2) 0.56374(14) 0.22742(14) 0.0215(5) Uani 1 1 d . . . . .
C7 C 0.1378(2) 0.51643(14) 0.17875(14) 0.0224(5) Uani 1 1 d . . . . .
H7 H 0.1728 0.4663 0.2064 0.027 Uiso 1 1 calc R U . . .
C8 C 0.0813(2) 0.48534(16) 0.10524(15) 0.0268(5) Uani 1 1 d . . . . .
H8A H 0.0606 0.4237 0.1075 0.032 Uiso 1 1 calc R U . . .
H8B H 0.0023 0.5174 0.0929 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1866(2) 0.50243(16) 0.04845(15) 0.0291(6) Uani 1 1 d . . . . .
H9A H 0.2526 0.4569 0.0492 0.035 Uiso 1 1 calc R U . . .
H9B H 0.1505 0.5070 -0.0019 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2416(2) 0.58757(16) 0.07432(15) 0.0290(6) Uani 1 1 d . . . . .
H10A H 0.1841 0.6355 0.0609 0.035 Uiso 1 1 calc R U . . .
H10B H 0.3274 0.5978 0.0526 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2505(2) 0.57752(14) 0.15806(13) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.2384 0.6342 0.1825 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4802(2) 0.58696(15) 0.18072(13) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.6052(2) 0.54363(14) 0.20089(14) 0.0235(5) Uani 1 1 d . . . . .
H14 H 0.6558 0.5822 0.2338 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6655(2) 0.44021(14) 0.28981(13) 0.0212(5) Uani 1 1 d . . . . .
C17 C 0.6289(2) 0.35819(14) 0.32748(14) 0.0206(5) Uani 1 1 d . . . . .
H17 H 0.6028 0.3149 0.2898 0.025 Uiso 1 1 calc R U . . .
C18 C 0.7410(2) 0.32320(16) 0.37356(15) 0.0262(6) Uani 1 1 d . . . . .
H18A H 0.7454 0.2602 0.3700 0.031 Uiso 1 1 calc R U . . .
H18B H 0.8236 0.3475 0.3567 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7118(2) 0.35095(17) 0.45203(15) 0.0296(6) Uani 1 1 d . . . . .
H19A H 0.7349 0.4116 0.4600 0.035 Uiso 1 1 calc R U . . .
H19B H 0.7580 0.3150 0.4883 0.035 Uiso 1 1 calc R U . . .
C20 C 0.5668(2) 0.33759(18) 0.45712(15) 0.0292(6) Uani 1 1 d . . . . .
H20A H 0.5303 0.3695 0.4993 0.035 Uiso 1 1 calc R U . . .
H20B H 0.5458 0.2763 0.4627 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5158(2) 0.37258(15) 0.38378(13) 0.0208(5) Uani 1 1 d . . . . .
H21 H 0.5005 0.4353 0.3891 0.025 Uiso 1 1 calc R U . . .
C23 C 0.2909(2) 0.37538(14) 0.34324(13) 0.0198(5) Uani 1 1 d . . . . .
C24 C 0.1787(2) 0.32170(14) 0.31452(13) 0.0203(5) Uani 1 1 d . . . . .
H24 H 0.1213 0.3595 0.2847 0.024 Uiso 1 1 calc R U . . .
C26 C 0.2919(2) 0.27109(14) 0.20701(14) 0.0210(5) Uani 1 1 d . . . . .
C28 C 0.4019(2) 0.20490(16) 0.10287(15) 0.0295(6) Uani 1 1 d . . . . .
C29 C 0.5326(3) 0.2404(2) 0.1220(2) 0.0481(8) Uani 1 1 d . . . . .
H29A H 0.5246 0.3010 0.1348 0.072 Uiso 1 1 calc R U . . .
H29B H 0.5901 0.2342 0.0796 0.072 Uiso 1 1 calc R U . . .
H29C H 0.5679 0.2090 0.1641 0.072 Uiso 1 1 calc R U . . .
C30 C 0.4134(4) 0.11176(19) 0.08034(19) 0.0502(9) Uani 1 1 d . . . . .
H30A H 0.4581 0.0799 0.1191 0.075 Uiso 1 1 calc R U . . .
H30B H 0.4621 0.1077 0.0343 0.075 Uiso 1 1 calc R U . . .
H30C H 0.3276 0.0876 0.0731 0.075 Uiso 1 1 calc R U . . .
C31 C 0.3349(3) 0.2560(2) 0.04407(17) 0.0434(7) Uani 1 1 d . . . . .
H31A H 0.2485 0.2330 0.0362 0.065 Uiso 1 1 calc R U . . .
H31B H 0.3839 0.2526 -0.0019 0.065 Uiso 1 1 calc R U . . .
H31C H 0.3287 0.3158 0.0597 0.065 Uiso 1 1 calc R U . . .
C33 C -0.0009(3) 0.56161(19) 0.42896(16) 0.0371(6) Uani 1 1 d . . . . .
H33A H -0.0369 0.5038 0.4280 0.056 Uiso 1 1 calc R U . . .
H33B H -0.0476 0.5962 0.4651 0.056 Uiso 1 1 calc R U . . .
H33C H 0.0899 0.5589 0.4427 0.056 Uiso 1 1 calc R U . . .
C36 C 0.6834(3) 0.52459(18) 0.13232(17) 0.0354(6) Uani 1 1 d . . . . .
H36A H 0.7670 0.5011 0.1466 0.053 Uiso 1 1 calc R U . . .
H36B H 0.6962 0.5774 0.1043 0.053 Uiso 1 1 calc R U . . .
H36C H 0.6376 0.4830 0.1018 0.053 Uiso 1 1 calc R U . . .
C39 C 0.1022(2) 0.28743(16) 0.37939(15) 0.0273(6) Uani 1 1 d . . . . .
H39A H 0.0264 0.2569 0.3612 0.041 Uiso 1 1 calc R U . . .
H39B H 0.0751 0.3351 0.4108 0.041 Uiso 1 1 calc R U . . .
H39C H 0.1559 0.2482 0.4080 0.041 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
O2 C1 1.452(3) . ?
O2 C3 1.330(3) . ?
O15 C14 1.450(3) . ?
O15 C16 1.346(3) . ?
O27 C26 1.345(3) . ?
O27 C28 1.475(3) . ?
O32 C3 1.197(3) . ?
O34 C6 1.231(3) . ?
O35 C13 1.235(3) . ?
O37 C16 1.200(3) . ?
O38 C23 1.233(3) . ?
O40 C26 1.214(3) . ?
N5 H5 0.8800 . ?
N5 C4 1.449(3) . ?
N5 C6 1.341(3) . ?
N12 H12 0.8800 . ?
N12 C11 1.466(3) . ?
N12 C13 1.334(3) . ?
N22 H22 0.8800 . ?
N22 C21 1.453(3) . ?
N22 C23 1.337(3) . ?
N25 H25 0.8800 . ?
N25 C24 1.451(3) . ?
N25 C26 1.361(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.525(3) . ?
C4 H4 1.0000 . ?
C4 C33 1.520(4) . ?
C6 C7 1.519(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.538(4) . ?
C7 C11 1.560(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.525(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.531(4) . ?
C11 H11 1.0000 . ?
C13 C14 1.514(3) . ?
C14 H14 1.0000 . ?
C14 C36 1.517(4) . ?
C16 C17 1.504(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.538(3) . ?
C17 C21 1.576(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.520(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.528(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.535(3) . ?
C21 H21 1.0000 . ?
C23 C24 1.532(3) . ?
C24 H24 1.0000 . ?
C24 C39 1.519(3) . ?
C28 C29 1.512(4) . ?
C28 C30 1.519(4) . ?
C28 C31 1.506(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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 O2 C1 114.4(2) . . ?
C16 O15 C14 115.92(17) . . ?
C26 O27 C28 119.86(18) . . ?
C4 N5 H5 119.4 . . ?
C6 N5 H5 119.4 . . ?
C6 N5 C4 121.24(19) . . ?
C11 N12 H12 119.8 . . ?
C13 N12 H12 119.8 . . ?
C13 N12 C11 120.46(18) . . ?
C21 N22 H22 118.3 . . ?
C23 N22 H22 118.3 . . ?
C23 N22 C21 123.37(19) . . ?
C24 N25 H25 120.9 . . ?
C26 N25 H25 120.9 . . ?
C26 N25 C24 118.30(19) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C3 C4 114.2(2) . . ?
O32 C3 O2 123.1(2) . . ?
O32 C3 C4 122.8(2) . . ?
N5 C4 C3 113.6(2) . . ?
N5 C4 H4 107.6 . . ?
N5 C4 C33 110.1(2) . . ?
C3 C4 H4 107.6 . . ?
C33 C4 C3 110.1(2) . . ?
C33 C4 H4 107.6 . . ?
O34 C6 N5 122.6(2) . . ?
O34 C6 C7 122.3(2) . . ?
N5 C6 C7 115.1(2) . . ?
C6 C7 H7 109.1 . . ?
C6 C7 C8 114.20(19) . . ?
C6 C7 C11 109.32(18) . . ?
C8 C7 H7 109.1 . . ?
C8 C7 C11 105.9(2) . . ?
C11 C7 H7 109.1 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 C7 104.8(2) . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 C8 102.4(2) . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
C9 C10 C11 103.8(2) . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
N12 C11 C7 110.09(17) . . ?
N12 C11 C10 111.7(2) . . ?
N12 C11 H11 110.0 . . ?
C7 C11 H11 110.0 . . ?
C10 C11 C7 104.87(19) . . ?
C10 C11 H11 110.0 . . ?
O35 C13 N12 123.1(2) . . ?
O35 C13 C14 118.7(2) . . ?
N12 C13 C14 118.11(19) . . ?
O15 C14 C13 109.16(18) . . ?
O15 C14 H14 109.1 . . ?
O15 C14 C36 109.8(2) . . ?
C13 C14 H14 109.1 . . ?
C13 C14 C36 110.6(2) . . ?
C36 C14 H14 109.1 . . ?
O15 C16 C17 112.24(19) . . ?
O37 C16 O15 122.6(2) . . ?
O37 C16 C17 125.1(2) . . ?
C16 C17 H17 109.7 . . ?
C16 C17 C18 111.02(19) . . ?
C16 C17 C21 111.26(18) . . ?
C18 C17 H17 109.7 . . ?
C18 C17 C21 105.41(19) . . ?
C21 C17 H17 109.7 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 C17 104.83(19) . . ?
C19 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C18 C19 H19A 111.3 . . ?
C18 C19 H19B 111.3 . . ?
C18 C19 C20 102.5(2) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
C19 C20 H20A 111.0 . . ?
C19 C20 H20B 111.0 . . ?
C19 C20 C21 103.9(2) . . ?
H20A C20 H20B 109.0 . . ?
C21 C20 H20A 111.0 . . ?
C21 C20 H20B 111.0 . . ?
N22 C21 C17 112.30(19) . . ?
N22 C21 C20 113.3(2) . . ?
N22 C21 H21 108.8 . . ?
C17 C21 H21 108.8 . . ?
C20 C21 C17 104.67(18) . . ?
C20 C21 H21 108.8 . . ?
O38 C23 N22 124.0(2) . . ?
O38 C23 C24 120.2(2) . . ?
N22 C23 C24 115.65(19) . . ?
N25 C24 C23 111.95(18) . . ?
N25 C24 H24 108.4 . . ?
N25 C24 C39 110.32(18) . . ?
C23 C24 H24 108.4 . . ?
C39 C24 C23 109.3(2) . . ?
C39 C24 H24 108.4 . . ?
O27 C26 N25 110.54(19) . . ?
O40 C26 O27 126.0(2) . . ?
O40 C26 N25 123.4(2) . . ?
O27 C28 C29 110.0(2) . . ?
O27 C28 C30 102.3(2) . . ?
O27 C28 C31 110.5(2) . . ?
C29 C28 C30 110.1(2) . . ?
C31 C28 C29 112.7(3) . . ?
C31 C28 C30 110.8(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C33 H33A 109.5 . . ?
C4 C33 H33B 109.5 . . ?
C4 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C14 C36 H36A 109.5 . . ?
C14 C36 H36B 109.5 . . ?
C14 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C24 C39 H39A 109.5 . . ?
C24 C39 H39B 109.5 . . ?
C24 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 N5 -12.0(3) . . . . ?
O2 C3 C4 C33 112.0(2) . . . . ?
O15 C16 C17 C18 169.71(19) . . . . ?
O15 C16 C17 C21 -73.2(2) . . . . ?
O32 C3 C4 N5 169.0(2) . . . . ?
O32 C3 C4 C33 -67.0(3) . . . . ?
O34 C6 C7 C8 -34.2(3) . . . . ?
O34 C6 C7 C11 84.2(3) . . . . ?
O35 C13 C14 O15 163.8(2) . . . . ?
O35 C13 C14 C36 -75.3(3) . . . . ?
O37 C16 C17 C18 -9.5(3) . . . . ?
O37 C16 C17 C21 107.6(3) . . . . ?
O38 C23 C24 N25 146.7(2) . . . . ?
O38 C23 C24 C39 -90.8(3) . . . . ?
N5 C6 C7 C8 148.3(2) . . . . ?
N5 C6 C7 C11 -93.3(2) . . . . ?
N12 C13 C14 O15 -18.9(3) . . . . ?
N12 C13 C14 C36 102.0(3) . . . . ?
N22 C23 C24 N25 -36.8(3) . . . . ?
N22 C23 C24 C39 85.7(2) . . . . ?
C1 O2 C3 O32 -1.7(4) . . . . ?
C1 O2 C3 C4 179.3(2) . . . . ?
C4 N5 C6 O34 -2.8(4) . . . . ?
C4 N5 C6 C7 174.62(19) . . . . ?
C6 N5 C4 C3 -72.7(3) . . . . ?
C6 N5 C4 C33 163.3(2) . . . . ?
C6 C7 C8 C9 139.4(2) . . . . ?
C6 C7 C11 N12 123.4(2) . . . . ?
C6 C7 C11 C10 -116.2(2) . . . . ?
C7 C8 C9 C10 -38.1(2) . . . . ?
C8 C7 C11 N12 -113.2(2) . . . . ?
C8 C7 C11 C10 7.2(2) . . . . ?
C8 C9 C10 C11 42.8(2) . . . . ?
C9 C10 C11 N12 88.4(2) . . . . ?
C9 C10 C11 C7 -30.8(2) . . . . ?
C11 N12 C13 O35 0.1(4) . . . . ?
C11 N12 C13 C14 -177.1(2) . . . . ?
C11 C7 C8 C9 19.1(2) . . . . ?
C13 N12 C11 C7 -167.8(2) . . . . ?
C13 N12 C11 C10 76.1(3) . . . . ?
C14 O15 C16 O37 -0.9(3) . . . . ?
C14 O15 C16 C17 179.86(19) . . . . ?
C16 O15 C14 C13 -149.7(2) . . . . ?
C16 O15 C14 C36 88.9(2) . . . . ?
C16 C17 C18 C19 99.0(2) . . . . ?
C16 C17 C21 N22 111.5(2) . . . . ?
C16 C17 C21 C20 -125.2(2) . . . . ?
C17 C18 C19 C20 39.8(2) . . . . ?
C18 C17 C21 N22 -128.0(2) . . . . ?
C18 C17 C21 C20 -4.8(2) . . . . ?
C18 C19 C20 C21 -42.9(3) . . . . ?
C19 C20 C21 N22 151.8(2) . . . . ?
C19 C20 C21 C17 29.2(3) . . . . ?
C21 N22 C23 O38 -7.5(4) . . . . ?
C21 N22 C23 C24 176.2(2) . . . . ?
C21 C17 C18 C19 -21.6(2) . . . . ?
C23 N22 C21 C17 -115.8(2) . . . . ?
C23 N22 C21 C20 125.9(2) . . . . ?
C24 N25 C26 O27 -178.67(18) . . . . ?
C24 N25 C26 O40 3.6(3) . . . . ?
C26 O27 C28 C29 61.7(3) . . . . ?
C26 O27 C28 C30 178.6(2) . . . . ?
C26 O27 C28 C31 -63.3(3) . . . . ?
C26 N25 C24 C23 -58.2(3) . . . . ?
C26 N25 C24 C39 179.90(19) . . . . ?
C28 O27 C26 O40 0.1(4) . . . . ?
C28 O27 C26 N25 -177.56(19) . . . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-3
####################################################################### 
# 
# 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_Aib-ACPC-Lac-ACPC-Ala-ACPC-Aib_moon226
_database_code_depnum_ccdc_archive 'CCDC 1448856'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H62 N6 O11'
_chemical_formula_sum            'C38 H62 N6 O11'
_chemical_formula_weight         778.93
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.7226(16)
_cell_length_b                   10.6558(17)
_cell_length_c                   21.682(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.429(5)
_cell_angle_gamma                90
_cell_volume                     2476.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2787
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      19.69
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0837 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.6986.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1605
_diffrn_reflns_av_unetI/netI     0.1975
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24592
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.047
_diffrn_reflns_theta_min         0.939
_diffrn_ambient_temperature      250.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3980
_reflns_number_total             9623
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_data_collection       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       0.0027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.792
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         9623
_refine_ls_number_restraints     478
_refine_ls_R_factor_all          0.1625
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      0.791
_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)+(0.0786P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1673
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Shared sites
{H19A, H19C}
2. Others
 Fixed Uiso: H5(0.05) H12(0.051) H15(0.057) H22(0.049) H32(0.055) H35(0.073)
 H2A(0.198) H2B(0.198) H2C(0.198) H7(0.047) H9A(0.089) H9B(0.089) H10A(0.086)
 H10B(0.086) H11(0.047) H14A(0.077) H14B(0.077) H15A(0.059) H17(0.061)
 H18A(0.096) H18B(0.096) H18C(0.096) H18D(0.096) H19A(0.128) H19B(0.128)
 H20A(0.109) H20B(0.109) H20C(0.109) H20D(0.109) H21(0.06) H24(0.046)
 H27(0.056) H28A(0.089) H28B(0.089) H29A(0.104) H29B(0.104) H30A(0.082)
 H30B(0.082) H31(0.053) H39A(0.215) H39B(0.215) H39C(0.215) H39D(0.2) H39E(0.2)
 H39F(0.2) H40A(0.175) H40B(0.175) H40C(0.175) H40D(0.17) H40E(0.17) H40F(0.17)
 H41A(0.177) H41B(0.177) H41C(0.177) H41D(0.181) H41E(0.181) H41F(0.181)
 H43A(0.092) H43B(0.092) H43C(0.092) H44A(0.101) H44B(0.101) H44C(0.101)
 H47A(0.108) H47B(0.108) H47C(0.108) H50A(0.107) H50B(0.107) H50C(0.107)
 H53A(0.131) H53B(0.131) H53C(0.131) H54A(0.104) H54B(0.104) H54C(0.104)
 H19C(0.086) H19D(0.086)
 Fixed X: H5(0.4122) H12(0.454) H15(0.5827) H22(0.7285) H32(1.0367)
 H35(1.1897) H2A(0.0202) H2B(-0.0783) H2C(0.0414) H7(0.4487) H9A(0.5124)
 H9B(0.4133) H10A(0.2638) H10B(0.3803) H11(0.2275) H14A(0.4597) H14B(0.3161)
 H15A(0.3605) H17(0.64) H18A(0.4414) H18B(0.5835) H18C(0.544) H18D(0.4378)
 H19A(0.5641) H19B(0.4556) H20A(0.6262) H20B(0.7157) H20C(0.586) H20D(0.7203)
 H21(0.5053) H24(0.7165) H27(0.9303) H28A(0.8293) H28B(0.7071) H29A(0.7723)
 H29B(0.8911) H30A(1.0172) H30B(0.918) H31(0.7954) H39A(1.2028) H39B(1.1556)
 H39C(1.0736) H39D(1.063) H39E(1.1205) H39F(1.1743) H40A(1.3831) H40B(1.3775)
 H40C(1.4134) H40D(1.3461) H40E(1.4241) H40F(1.337) H41A(1.0771) H41B(1.1669)
 H41C(1.2107) H41D(1.1676) H41E(1.0835) H41F(1.2189) H43A(0.222) H43B(0.1349)
 H43C(0.1115) H44A(0.4016) H44B(0.3092) H44C(0.4125) H47A(0.5382) H47B(0.4284)
 H47C(0.5371) H50A(0.9065) H50B(0.8147) H50C(0.9067) H53A(1.011) H53B(0.8844)
 H53C(0.9119) H54A(1.102) H54B(0.9877) H54C(1.114) H19C(0.5593) H19D(0.6824)
 Fixed Y: H5(0.1509) H12(0.471) H15(0.5025) H22(0.3041) H32(0.5852)
 H35(0.4414) H2A(0.0077) H2B(-0.0694) H2C(-0.1373) H7(0.346) H9A(0.5513)
 H9B(0.5866) H10A(0.6164) H10B(0.6623) H11(0.4769) H14A(0.3575) H14B(0.3952)
 H15A(0.6099) H17(0.3297) H18A(0.2125) H18B(0.2056) H18C(0.2331) H18D(0.1748)
 H19A(0.0025) H19B(0.034) H20A(0.0049) H20B(0.0811) H20C(0.0038) H20D(0.063)
 H21(0.1853) H24(0.2985) H27(0.5864) H28A(0.7294) H28B(0.7239) H29A(0.8833)
 H29B(0.8929) H30A(0.7857) H30B(0.8355) H31(0.6571) H39A(0.8427) H39B(0.9236)
 H39C(0.8108) H39D(0.7897) H39E(0.7962) H39F(0.8832) H40A(0.6543) H40B(0.7783)
 H40C(0.7858) H40D(0.8032) H40E(0.7592) H40F(0.8789) H41A(0.7234) H41B(0.8322)
 H41C(0.6905) H41D(0.5458) H41E(0.6653) H41F(0.6568) H43A(0.0845) H43B(-0.0239)
 H43C(0.117) H44A(-0.0915) H44B(-0.143) H44C(-0.0431) H47A(0.7304) H47B(0.7836)
 H47C(0.7047) H50A(0.2128) H50B(0.1046) H50C(0.1669) H53A(0.2691) H53B(0.267)
 H53C(0.3779) H54A(0.3462) H54B(0.2568) H54C(0.2426) H19C(0.0064) H19D(0.0876)
 Fixed Z: H5(0.1156) H12(0.1744) H15(0.2781) H22(0.236) H32(0.2544) H35(0.33)
 H2A(-0.0245) H2B(0.0134) H2C(-0.012) H7(0.0966) H9A(0.029) H9B(-0.0242)
 H10A(0.0405) H10B(0.0814) H11(0.1122) H14A(-0.0091) H14B(-0.0179) H15A(0.3033)
 H17(0.3336) H18A(0.3852) H18B(0.4079) H18C(0.4128) H18D(0.3688) H19A(0.3777)
 H19B(0.3284) H20A(0.2672) H20B(0.3141) H20C(0.2776) H20D(0.2907) H21(0.245)
 H24(0.0813) H27(0.1321) H28A(0.0748) H28B(0.1149) H29A(0.1692) H29B(0.127)
 H30A(0.1979) H30B(0.2461) H31(0.2358) H39A(0.3404) H39B(0.3965) H39C(0.3706)
 H39D(0.4444) H39E(0.3779) H39F(0.4315) H40A(0.4392) H40B(0.4793) H40C(0.409)
 H40D(0.3737) H40E(0.4328) H40F(0.4363) H41A(0.479) H41B(0.5025) H41C(0.5074)
 H41D(0.4952) H41E(0.5067) H41F(0.5373) H43A(0.2048) H43B(0.1782) H43C(0.1576)
 H44A(0.0944) H44B(0.1444) H44C(0.1634) H47A(0.2937) H47B(0.2511) H47C(0.2218)
 H50A(0.0738) H50B(0.0939) H50C(0.1433) H53A(0.3908) H53B(0.3515) H53C(0.3986)
 H54A(0.2395) H54B(0.2528) H54C(0.2917) H19C(0.3766) H19D(0.3879)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.0776(4) -0.0301(5) 0.0618(2) 0.0669(15) Uani 1 1 d . . . . .
O25 O 0.8261(4) 0.3878(3) 0.14362(17) 0.0372(10) Uani 1 1 d . . . . .
O37 O 1.2076(19) 0.632(2) 0.3894(9) 0.083(6) Uani 0.61(3) 1 d . . P A 1
O37A O 1.214(3) 0.593(4) 0.399(2) 0.103(10) Uani 0.39(3) 1 d . . P A 2
O42 O 0.2441(5) 0.0007(6) 0.0050(2) 0.0842(17) Uani 1 1 d . . . . .
O45 O 0.1741(4) 0.2606(4) 0.0670(2) 0.0615(13) Uani 1 1 d . . . . .
O46 O 0.2246(4) 0.6086(4) 0.2127(2) 0.0593(13) Uani 1 1 d . . . . .
O48 O 0.3506(4) 0.3603(4) 0.3085(2) 0.0686(15) Uani 1 1 d . . . . .
O49 O 0.5920(4) 0.1439(4) 0.1416(2) 0.0557(12) Uani 1 1 d . . . . .
O51 O 0.6529(4) 0.5031(4) 0.14070(19) 0.0453(11) Uani 1 1 d . . . . .
O52 O 0.8024(4) 0.4532(4) 0.28737(18) 0.0442(11) Uani 1 1 d . . . . .
O55 O 1.0016(5) 0.6020(6) 0.3961(2) 0.094(2) Uani 1 1 d . . . . .
N5 N 0.3332(5) 0.1509(4) 0.1054(2) 0.0414(13) Uani 1 1 d . . . . .
H5 H 0.4122 0.1509 0.1156 0.050 Uiso 1 1 calc R . . . .
N12 N 0.3806(4) 0.5042(5) 0.1681(2) 0.0423(13) Uani 1 1 d . . . . .
H12 H 0.4540 0.4710 0.1744 0.051 Uiso 1 1 calc R . . . .
N15 N 0.5032(5) 0.4912(5) 0.2828(2) 0.0474(13) Uani 1 1 d . . . . .
H15 H 0.5827 0.5025 0.2781 0.057 Uiso 1 1 calc R . . . .
N22 N 0.6712(4) 0.2522(4) 0.2228(2) 0.0407(13) Uani 1 1 d . . . . .
H22 H 0.7285 0.3041 0.2360 0.049 Uiso 1 1 calc R . . . .
N32 N 0.9570(5) 0.5701(5) 0.2531(2) 0.0460(14) Uani 1 1 d . . . . .
H32 H 1.0367 0.5852 0.2544 0.055 Uiso 1 1 calc R . . . .
N35 N 1.1154(5) 0.4651(6) 0.3404(2) 0.0607(16) Uani 1 1 d . . . . .
H35 H 1.1897 0.4414 0.3300 0.073 Uiso 1 1 calc R . . . .
C2 C 0.0096(9) -0.0597(13) 0.0049(4) 0.132(5) Uani 1 1 d . . . . .
H2A H 0.0202 0.0077 -0.0245 0.198 Uiso 1 1 calc GR . . . .
H2B H -0.0783 -0.0694 0.0134 0.198 Uiso 1 1 calc GR . . . .
H2C H 0.0414 -0.1373 -0.0120 0.198 Uiso 1 1 calc GR . . . .
C3 C 0.1931(6) 0.0044(7) 0.0528(3) 0.0497(16) Uani 1 1 d . . . . .
C4 C 0.2627(6) 0.0373(5) 0.1150(3) 0.0421(15) Uani 1 1 d . . . . .
C6 C 0.2839(6) 0.2556(5) 0.0817(3) 0.0379(15) Uani 1 1 d . . . . .
C7 C 0.3673(6) 0.3672(5) 0.0767(3) 0.0394(15) Uani 1 1 d . . . . .
H7 H 0.4487 0.3460 0.0966 0.047 Uiso 1 1 calc R . . . .
C9 C 0.4253(8) 0.5421(7) 0.0150(4) 0.074(2) Uani 1 1 d . . . . .
H9A H 0.5124 0.5513 0.0290 0.089 Uiso 1 1 calc R . . . .
H9B H 0.4133 0.5866 -0.0242 0.089 Uiso 1 1 calc R . . . .
C10 C 0.3426(9) 0.5897(6) 0.0604(3) 0.072(2) Uani 1 1 d . . . . .
H10A H 0.2638 0.6164 0.0405 0.086 Uiso 1 1 calc R . . . .
H10B H 0.3803 0.6623 0.0814 0.086 Uiso 1 1 calc R . . . .
C11 C 0.3186(6) 0.4853(6) 0.1068(3) 0.0393(14) Uani 1 1 d . . . . .
H11 H 0.2275 0.4769 0.1122 0.047 Uiso 1 1 calc R . . . .
C13 C 0.3313(6) 0.5689(6) 0.2144(3) 0.0417(15) Uani 1 1 d . . . . .
C14 C 0.3912(8) 0.4060(6) 0.0082(3) 0.064(2) Uani 1 1 d . . . . .
H14A H 0.4597 0.3575 -0.0091 0.077 Uiso 1 1 calc R . . . .
H14B H 0.3161 0.3952 -0.0179 0.077 Uiso 1 1 calc R . . . .
C15 C 0.4135(7) 0.5967(6) 0.2671(3) 0.0492(17) Uani 1 1 d . . . . .
H15A H 0.3605 0.6099 0.3033 0.059 Uiso 1 1 calc R . . . .
C16 C 0.4633(6) 0.3816(7) 0.3037(3) 0.0461(16) Uani 1 1 d . . . . .
C17 C 0.5618(6) 0.2858(6) 0.3214(3) 0.0507(17) Uani 1 1 d . . . . .
H17 H 0.6400 0.3297 0.3336 0.061 Uiso 1 1 calc R . . . .
C18 C 0.5267(9) 0.1958(8) 0.3721(4) 0.080(2) Uani 1 1 d . . . . .
H18A H 0.4414 0.2125 0.3852 0.096 Uiso 0.75(5) 1 calc R . P B 1
H18B H 0.5835 0.2056 0.4079 0.096 Uiso 0.75(5) 1 calc R . P B 1
H18C H 0.5440 0.2331 0.4128 0.096 Uiso 0.25(5) 1 calc R . P B 2
H18D H 0.4378 0.1748 0.3688 0.096 Uiso 0.25(5) 1 calc R . P B 2
C19 C 0.536(4) 0.0620(14) 0.3458(12) 0.107(7) Uani 0.75(5) 1 d . . P B 1
H19A H 0.5641 0.0025 0.3777 0.128 Uiso 0.75(5) 1 calc R . P B 1
H19B H 0.4556 0.0340 0.3284 0.128 Uiso 0.75(5) 1 calc R . P B 1
C20 C 0.6308(10) 0.0746(7) 0.2967(4) 0.091(3) Uani 1 1 d . . . . .
H20A H 0.6262 0.0049 0.2672 0.109 Uiso 0.75(5) 1 calc R . P B 1
H20B H 0.7157 0.0811 0.3141 0.109 Uiso 0.75(5) 1 calc R . P B 1
H20C H 0.5860 0.0038 0.2776 0.109 Uiso 0.25(5) 1 calc R . P B 2
H20D H 0.7203 0.0630 0.2907 0.109 Uiso 0.25(5) 1 calc R . P B 2
C21 C 0.5860(6) 0.2009(6) 0.2668(3) 0.0503(17) Uani 1 1 d . . . . .
H21 H 0.5053 0.1853 0.2450 0.060 Uiso 1 1 calc R . . . .
C23 C 0.6660(5) 0.2235(6) 0.1628(3) 0.0385(15) Uani 1 1 d . . . . .
C24 C 0.7601(6) 0.2758(5) 0.1205(3) 0.0381(15) Uani 1 1 d . . . . .
H24 H 0.7165 0.2985 0.0813 0.046 Uiso 1 1 calc R . . . .
C26 C 0.7660(6) 0.4970(6) 0.1434(2) 0.0322(13) Uani 1 1 d . . . . .
C27 C 0.8496(6) 0.6081(6) 0.1506(3) 0.0463(16) Uani 1 1 d . . . . .
H27 H 0.9303 0.5864 0.1321 0.056 Uiso 1 1 calc R . . . .
C28 C 0.7985(8) 0.7257(6) 0.1169(4) 0.074(2) Uani 1 1 d . . . . .
H28A H 0.8293 0.7294 0.0748 0.089 Uiso 1 1 calc R . . . .
H28B H 0.7071 0.7239 0.1149 0.089 Uiso 1 1 calc R . . . .
C29 C 0.8433(9) 0.8366(8) 0.1532(4) 0.086(3) Uani 1 1 d . . . . .
H29A H 0.7723 0.8833 0.1692 0.104 Uiso 1 1 calc R . . . .
H29B H 0.8911 0.8929 0.1270 0.104 Uiso 1 1 calc R . . . .
C30 C 0.9288(8) 0.7862(6) 0.2084(4) 0.068(2) Uani 1 1 d . . . . .
H30A H 1.0172 0.7857 0.1979 0.082 Uiso 1 1 calc R . . . .
H30B H 0.9180 0.8355 0.2461 0.082 Uiso 1 1 calc R . . . .
C31 C 0.8763(6) 0.6505(5) 0.2151(3) 0.0443(16) Uani 1 1 d . . . . .
H31 H 0.7954 0.6571 0.2358 0.053 Uiso 1 1 calc R . . . .
C33 C 0.9141(6) 0.4754(6) 0.2858(2) 0.0350(14) Uani 1 1 d . . . . .
C34 C 1.0107(6) 0.3954(6) 0.3184(3) 0.0464(16) Uani 1 1 d . . . . .
C36 C 1.1037(7) 0.5700(9) 0.3779(4) 0.068(2) Uani 1 1 d . . . . .
C38 C 1.218(3) 0.760(3) 0.4193(11) 0.097(7) Uani 0.61(3) 1 d . . P A 1
C38A C 1.227(4) 0.705(5) 0.439(2) 0.118(11) Uani 0.39(3) 1 d . . P A 2
C39 C 1.158(2) 0.840(3) 0.3787(13) 0.143(9) Uani 0.61(3) 1 d . . P A 1
H39A H 1.2028 0.8427 0.3404 0.215 Uiso 0.61(3) 1 calc GR . P A 1
H39B H 1.1556 0.9236 0.3965 0.215 Uiso 0.61(3) 1 calc GR . P A 1
H39C H 1.0736 0.8108 0.3706 0.215 Uiso 0.61(3) 1 calc GR . P A 1
C39A C 1.139(4) 0.801(4) 0.422(2) 0.134(12) Uani 0.39(3) 1 d . . P A 2
H39D H 1.0630 0.7897 0.4444 0.200 Uiso 0.39(3) 1 calc GR . P A 2
H39E H 1.1205 0.7962 0.3779 0.200 Uiso 0.39(3) 1 calc GR . P A 2
H39F H 1.1743 0.8832 0.4315 0.200 Uiso 0.39(3) 1 calc GR . P A 2
C40 C 1.362(2) 0.743(3) 0.4386(15) 0.116(9) Uani 0.61(3) 1 d . . P A 1
H40A H 1.3831 0.6543 0.4392 0.175 Uiso 0.61(3) 1 calc GR . P A 1
H40B H 1.3775 0.7783 0.4793 0.175 Uiso 0.61(3) 1 calc GR . P A 1
H40C H 1.4134 0.7858 0.4090 0.175 Uiso 0.61(3) 1 calc GR . P A 1
C40A C 1.346(4) 0.796(5) 0.418(2) 0.113(12) Uani 0.39(3) 1 d . . P A 2
H40D H 1.3461 0.8032 0.3737 0.170 Uiso 0.39(3) 1 calc GR . P A 2
H40E H 1.4241 0.7592 0.4328 0.170 Uiso 0.39(3) 1 calc GR . P A 2
H40F H 1.3370 0.8789 0.4363 0.170 Uiso 0.39(3) 1 calc GR . P A 2
C41 C 1.1633(17) 0.751(3) 0.4827(9) 0.118(9) Uani 0.61(3) 1 d . . P A 1
H41A H 1.0771 0.7234 0.4790 0.177 Uiso 0.61(3) 1 calc GR . P A 1
H41B H 1.1669 0.8322 0.5025 0.177 Uiso 0.61(3) 1 calc GR . P A 1
H41C H 1.2107 0.6905 0.5074 0.177 Uiso 0.61(3) 1 calc GR . P A 1
C41A C 1.168(3) 0.636(5) 0.5011(13) 0.121(11) Uani 0.39(3) 1 d . . P A 2
H41D H 1.1676 0.5458 0.4952 0.181 Uiso 0.39(3) 1 calc GR . P A 2
H41E H 1.0835 0.6653 0.5067 0.181 Uiso 0.39(3) 1 calc GR . P A 2
H41F H 1.2189 0.6568 0.5373 0.181 Uiso 0.39(3) 1 calc GR . P A 2
C43 C 0.1747(7) 0.0554(7) 0.1688(3) 0.0614(19) Uani 1 1 d . . . . .
H43A H 0.2220 0.0845 0.2048 0.092 Uiso 1 1 calc GR . . . .
H43B H 0.1349 -0.0239 0.1782 0.092 Uiso 1 1 calc GR . . . .
H43C H 0.1115 0.1170 0.1576 0.092 Uiso 1 1 calc GR . . . .
C44 C 0.3551(7) -0.0701(6) 0.1308(4) 0.067(2) Uani 1 1 d . . . . .
H44A H 0.4016 -0.0915 0.0944 0.101 Uiso 1 1 calc GR . . . .
H44B H 0.3092 -0.1430 0.1444 0.101 Uiso 1 1 calc GR . . . .
H44C H 0.4125 -0.0431 0.1634 0.101 Uiso 1 1 calc GR . . . .
C47 C 0.4856(8) 0.7140(7) 0.2576(4) 0.072(2) Uani 1 1 d . . . . .
H47A H 0.5382 0.7304 0.2937 0.108 Uiso 1 1 calc GR . . . .
H47B H 0.4284 0.7836 0.2511 0.108 Uiso 1 1 calc GR . . . .
H47C H 0.5371 0.7047 0.2218 0.108 Uiso 1 1 calc GR . . . .
C50 C 0.8550(7) 0.1822(7) 0.1067(4) 0.071(2) Uani 1 1 d . . . . .
H50A H 0.9065 0.2128 0.0738 0.107 Uiso 1 1 calc GR . . . .
H50B H 0.8147 0.1046 0.0939 0.107 Uiso 1 1 calc GR . . . .
H50C H 0.9067 0.1669 0.1433 0.107 Uiso 1 1 calc GR . . . .
C53 C 0.9488(7) 0.3205(9) 0.3695(4) 0.087(3) Uani 1 1 d . . . . .
H53A H 1.0110 0.2691 0.3908 0.131 Uiso 1 1 calc GR . . . .
H53B H 0.8844 0.2670 0.3515 0.131 Uiso 1 1 calc GR . . . .
H53C H 0.9119 0.3779 0.3986 0.131 Uiso 1 1 calc GR . . . .
C54 C 1.0579(7) 0.3018(7) 0.2713(4) 0.069(2) Uani 1 1 d . . . . .
H54A H 1.1020 0.3462 0.2395 0.104 Uiso 1 1 calc GR . . . .
H54B H 0.9877 0.2568 0.2528 0.104 Uiso 1 1 calc GR . . . .
H54C H 1.1140 0.2426 0.2917 0.104 Uiso 1 1 calc GR . . . .
C19A C 0.604(6) 0.081(4) 0.364(2) 0.071(10) Uani 0.25(5) 1 d . . P B 2
H19C H 0.5593 0.0064 0.3766 0.086 Uiso 0.25(5) 1 calc R . P B 2
H19D H 0.6824 0.0876 0.3879 0.086 Uiso 0.25(5) 1 calc R . P B 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
O2 C2 1.450(9) . ?
O2 C3 1.311(7) . ?
O25 C24 1.469(7) . ?
O25 C26 1.330(7) . ?
O37 C36 1.311(19) . ?
O37 C38 1.51(3) . ?
O37A C36 1.29(3) . ?
O37A C38A 1.48(5) . ?
O42 C3 1.185(7) . ?
O45 C6 1.213(7) . ?
O46 C13 1.220(7) . ?
O48 C16 1.236(7) . ?
O49 C23 1.241(7) . ?
O51 C26 1.214(6) . ?
O52 C33 1.222(6) . ?
O55 C36 1.221(8) . ?
N5 C4 1.445(7) . ?
N5 C6 1.332(7) . ?
N12 C11 1.486(7) . ?
N12 C13 1.337(8) . ?
N15 C15 1.513(8) . ?
N15 C16 1.327(8) . ?
N22 C21 1.444(8) . ?
N22 C23 1.336(7) . ?
N32 C31 1.458(8) . ?
N32 C33 1.322(7) . ?
N35 C34 1.419(8) . ?
N35 C36 1.391(10) . ?
C3 C4 1.563(9) . ?
C4 C43 1.532(9) . ?
C4 C44 1.546(9) . ?
C6 C7 1.494(8) . ?
C7 C11 1.517(8) . ?
C7 C14 1.569(9) . ?
C9 C10 1.433(11) . ?
C9 C14 1.502(9) . ?
C10 C11 1.526(9) . ?
C13 C15 1.456(9) . ?
C15 C47 1.486(10) . ?
C16 C17 1.513(9) . ?
C17 C18 1.513(10) . ?
C17 C21 1.518(9) . ?
C18 C19 1.54(2) . ?
C18 C19A 1.49(4) . ?
C19 C20 1.50(2) . ?
C20 C21 1.563(10) . ?
C20 C19A 1.48(4) . ?
C23 C24 1.489(9) . ?
C24 C50 1.461(9) . ?
C26 C27 1.491(9) . ?
C27 C28 1.544(9) . ?
C27 C31 1.490(9) . ?
C28 C29 1.492(11) . ?
C29 C30 1.584(11) . ?
C30 C31 1.560(9) . ?
C33 C34 1.504(8) . ?
C34 C53 1.531(10) . ?
C34 C54 1.523(9) . ?
C38 C39 1.38(3) . ?
C38 C40 1.60(4) . ?
C38 C41 1.51(3) . ?
C38A C39A 1.44(6) . ?
C38A C40A 1.67(7) . ?
C38A C41A 1.67(5) . ?

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 O2 C2 113.1(6) . . ?
C26 O25 C24 118.8(4) . . ?
C36 O37 C38 125.9(18) . . ?
C36 O37A C38A 116(3) . . ?
C6 N5 C4 123.6(5) . . ?
C13 N12 C11 124.4(5) . . ?
C16 N15 C15 121.5(5) . . ?
C23 N22 C21 123.0(5) . . ?
C33 N32 C31 122.9(5) . . ?
C36 N35 C34 122.4(6) . . ?
O2 C3 C4 111.6(6) . . ?
O42 C3 O2 125.3(6) . . ?
O42 C3 C4 122.7(6) . . ?
N5 C4 C3 107.7(5) . . ?
N5 C4 C43 109.8(5) . . ?
N5 C4 C44 108.5(5) . . ?
C43 C4 C3 113.3(5) . . ?
C43 C4 C44 109.1(6) . . ?
C44 C4 C3 108.3(5) . . ?
O45 C6 N5 120.7(5) . . ?
O45 C6 C7 121.7(5) . . ?
N5 C6 C7 117.5(5) . . ?
C6 C7 C11 114.6(5) . . ?
C6 C7 C14 113.0(5) . . ?
C11 C7 C14 104.7(5) . . ?
C10 C9 C14 104.9(7) . . ?
C9 C10 C11 108.2(6) . . ?
N12 C11 C7 110.2(5) . . ?
N12 C11 C10 114.3(5) . . ?
C7 C11 C10 104.8(5) . . ?
O46 C13 N12 123.0(6) . . ?
O46 C13 C15 120.2(6) . . ?
N12 C13 C15 116.8(6) . . ?
C9 C14 C7 101.9(6) . . ?
C13 C15 N15 113.2(5) . . ?
C13 C15 C47 111.7(6) . . ?
C47 C15 N15 109.1(6) . . ?
O48 C16 N15 121.0(6) . . ?
O48 C16 C17 122.2(6) . . ?
N15 C16 C17 116.8(6) . . ?
C16 C17 C21 109.6(5) . . ?
C18 C17 C16 115.3(6) . . ?
C18 C17 C21 103.9(6) . . ?
C17 C18 C19 107.3(8) . . ?
C19A C18 C17 106.1(16) . . ?
C20 C19 C18 103.4(15) . . ?
C19 C20 C21 99.6(10) . . ?
C19A C20 C21 107.4(16) . . ?
N22 C21 C17 114.4(5) . . ?
N22 C21 C20 114.0(6) . . ?
C17 C21 C20 104.3(6) . . ?
O49 C23 N22 121.8(6) . . ?
O49 C23 C24 117.6(6) . . ?
N22 C23 C24 120.1(5) . . ?
O25 C24 C23 114.9(5) . . ?
C50 C24 O25 107.1(5) . . ?
C50 C24 C23 110.9(5) . . ?
O25 C26 C27 113.8(5) . . ?
O51 C26 O25 122.0(6) . . ?
O51 C26 C27 124.1(6) . . ?
C26 C27 C28 112.9(5) . . ?
C31 C27 C26 116.0(5) . . ?
C31 C27 C28 104.8(6) . . ?
C29 C28 C27 106.7(6) . . ?
C28 C29 C30 107.6(6) . . ?
C31 C30 C29 100.4(6) . . ?
N32 C31 C27 116.8(5) . . ?
N32 C31 C30 112.7(5) . . ?
C27 C31 C30 104.8(5) . . ?
O52 C33 N32 121.1(5) . . ?
O52 C33 C34 122.7(6) . . ?
N32 C33 C34 116.1(5) . . ?
N35 C34 C33 113.0(6) . . ?
N35 C34 C53 112.6(6) . . ?
N35 C34 C54 107.2(5) . . ?
C33 C34 C53 109.2(5) . . ?
C33 C34 C54 107.1(5) . . ?
C54 C34 C53 107.5(6) . . ?
O37 C36 N35 115.1(11) . . ?
O37A C36 N35 105.6(19) . . ?
O55 C36 O37 124.3(12) . . ?
O55 C36 O37A 130.9(19) . . ?
O55 C36 N35 120.6(7) . . ?
O37 C38 C40 94(2) . . ?
C39 C38 O37 104.9(18) . . ?
C39 C38 C40 132(2) . . ?
C39 C38 C41 116(3) . . ?
C41 C38 O37 107.9(18) . . ?
C41 C38 C40 99(2) . . ?
O37A C38A C40A 112(4) . . ?
O37A C38A C41A 94(3) . . ?
C39A C38A O37A 112(3) . . ?
C39A C38A C40A 91(4) . . ?
C39A C38A C41A 105(4) . . ?
C40A C38A C41A 141(3) . . ?
C18 C19A C20 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 N5 -136.6(6) . . . . ?
O2 C3 C4 C43 -15.0(8) . . . . ?
O2 C3 C4 C44 106.2(6) . . . . ?
O25 C26 C27 C28 148.8(6) . . . . ?
O25 C26 C27 C31 -90.2(6) . . . . ?
O42 C3 C4 N5 49.8(9) . . . . ?
O42 C3 C4 C43 171.5(7) . . . . ?
O42 C3 C4 C44 -67.4(9) . . . . ?
O45 C6 C7 C11 51.2(8) . . . . ?
O45 C6 C7 C14 -68.6(8) . . . . ?
O46 C13 C15 N15 145.8(6) . . . . ?
O46 C13 C15 C47 -90.7(8) . . . . ?
O48 C16 C17 C18 -29.3(10) . . . . ?
O48 C16 C17 C21 87.4(8) . . . . ?
O49 C23 C24 O25 167.2(5) . . . . ?
O49 C23 C24 C50 -71.2(7) . . . . ?
O51 C26 C27 C28 -34.7(9) . . . . ?
O51 C26 C27 C31 86.3(7) . . . . ?
O52 C33 C34 N35 -147.0(6) . . . . ?
O52 C33 C34 C53 -20.8(9) . . . . ?
O52 C33 C34 C54 95.3(7) . . . . ?
N5 C6 C7 C11 -126.1(6) . . . . ?
N5 C6 C7 C14 114.1(6) . . . . ?
N12 C13 C15 N15 -37.2(8) . . . . ?
N12 C13 C15 C47 86.3(7) . . . . ?
N15 C16 C17 C18 150.3(7) . . . . ?
N15 C16 C17 C21 -93.0(7) . . . . ?
N22 C23 C24 O25 -19.9(7) . . . . ?
N22 C23 C24 C50 101.7(7) . . . . ?
N32 C33 C34 N35 35.4(7) . . . . ?
N32 C33 C34 C53 161.5(6) . . . . ?
N32 C33 C34 C54 -82.3(6) . . . . ?
C2 O2 C3 O42 -7.5(12) . . . . ?
C2 O2 C3 C4 179.2(7) . . . . ?
C4 N5 C6 O45 0.4(10) . . . . ?
C4 N5 C6 C7 177.7(5) . . . . ?
C6 N5 C4 C3 52.0(8) . . . . ?
C6 N5 C4 C43 -71.8(8) . . . . ?
C6 N5 C4 C44 169.0(6) . . . . ?
C6 C7 C11 N12 100.5(6) . . . . ?
C6 C7 C11 C10 -136.0(6) . . . . ?
C6 C7 C14 C9 156.4(6) . . . . ?
C9 C10 C11 N12 107.7(7) . . . . ?
C9 C10 C11 C7 -13.2(8) . . . . ?
C10 C9 C14 C7 -39.7(8) . . . . ?
C11 N12 C13 O46 7.4(9) . . . . ?
C11 N12 C13 C15 -169.5(5) . . . . ?
C11 C7 C14 C9 31.1(7) . . . . ?
C13 N12 C11 C7 -155.1(5) . . . . ?
C13 N12 C11 C10 87.2(7) . . . . ?
C14 C7 C11 N12 -135.2(5) . . . . ?
C14 C7 C11 C10 -11.7(7) . . . . ?
C14 C9 C10 C11 33.8(9) . . . . ?
C15 N15 C16 O48 3.1(10) . . . . ?
C15 N15 C16 C17 -176.5(5) . . . . ?
C16 N15 C15 C13 -66.6(8) . . . . ?
C16 N15 C15 C47 168.4(6) . . . . ?
C16 C17 C18 C19 121.9(19) . . . . ?
C16 C17 C18 C19A 156(3) . . . . ?
C16 C17 C21 N22 82.4(7) . . . . ?
C16 C17 C21 C20 -152.4(6) . . . . ?
C17 C18 C19 C20 27(3) . . . . ?
C17 C18 C19A C20 -28(4) . . . . ?
C18 C17 C21 N22 -153.8(6) . . . . ?
C18 C17 C21 C20 -28.6(8) . . . . ?
C18 C19 C20 C21 -43(2) . . . . ?
C18 C19 C20 C19A 65(3) . . . . ?
C19 C18 C19A C20 69(4) . . . . ?
C19 C20 C21 N22 170.5(17) . . . . ?
C19 C20 C21 C17 45.0(18) . . . . ?
C19 C20 C19A C18 -71(4) . . . . ?
C21 N22 C23 O49 -4.9(8) . . . . ?
C21 N22 C23 C24 -177.4(5) . . . . ?
C21 C17 C18 C19 1.9(19) . . . . ?
C21 C17 C18 C19A 36(3) . . . . ?
C21 C20 C19A C18 10(4) . . . . ?
C23 N22 C21 C17 -150.8(6) . . . . ?
C23 N22 C21 C20 89.3(7) . . . . ?
C24 O25 C26 O51 19.8(7) . . . . ?
C24 O25 C26 C27 -163.6(5) . . . . ?
C26 O25 C24 C23 -74.7(6) . . . . ?
C26 O25 C24 C50 161.6(5) . . . . ?
C26 C27 C28 C29 149.0(7) . . . . ?
C26 C27 C31 N32 71.2(7) . . . . ?
C26 C27 C31 C30 -163.3(6) . . . . ?
C27 C28 C29 C30 2.6(10) . . . . ?
C28 C27 C31 N32 -163.5(6) . . . . ?
C28 C27 C31 C30 -38.0(7) . . . . ?
C28 C29 C30 C31 -24.5(9) . . . . ?
C29 C30 C31 N32 166.2(6) . . . . ?
C29 C30 C31 C27 38.2(7) . . . . ?
C31 N32 C33 O52 -2.6(9) . . . . ?
C31 N32 C33 C34 175.1(5) . . . . ?
C31 C27 C28 C29 21.8(8) . . . . ?
C33 N32 C31 C27 -87.4(7) . . . . ?
C33 N32 C31 C30 151.1(6) . . . . ?
C34 N35 C36 O37 -173.5(13) . . . . ?
C34 N35 C36 O37A 167(2) . . . . ?
C34 N35 C36 O55 3.9(11) . . . . ?
C36 O37 C38 C39 -64(3) . . . . ?
C36 O37 C38 C40 160(3) . . . . ?
C36 O37 C38 C41 60(3) . . . . ?
C36 O37A C38A C39A -31(6) . . . . ?
C36 O37A C38A C40A -131(5) . . . . ?
C36 O37A C38A C41A 78(4) . . . . ?
C36 N35 C34 C33 53.6(8) . . . . ?
C36 N35 C34 C53 -70.7(9) . . . . ?
C36 N35 C34 C54 171.3(6) . . . . ?
C38 O37 C36 O37A -124(8) . . . . ?
C38 O37 C36 O55 -8(3) . . . . ?
C38 O37 C36 N35 169.0(17) . . . . ?
C38A O37A C36 O37 57(6) . . . . ?
C38A O37A C36 O55 -22(5) . . . . ?
C38A O37A C36 N35 177(3) . . . . ?
C19A C18 C19 C20 -66(3) . . . . ?
C19A C20 C21 N22 138(3) . . . . ?
C19A C20 C21 C17 12(3) . . . . ?

_platon_squeeze_details          
;
 ?
;
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.500 -0.190 0.500 383 10

