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

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1503995'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H45 N3 O9'
_chemical_formula_sum            'C30 H45 N3 O9'
_chemical_formula_weight         591.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.627(2)
_cell_length_b                   7.3150(10)
_cell_length_c                   23.510(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.567(8)
_cell_angle_gamma                90
_cell_volume                     3069.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      56.916
_cell_measurement_theta_min      3.836
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0826 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_av_unetI/netI     0.1318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2353
_reflns_number_total             5625
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.2020
_refine_ls_R_factor_gt           0.0884
_refine_ls_restrained_S_all      0.982
_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)+(0.1243P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2795
_refine_special_details          
;

 The high aspect ratio with small minimum axis of the 
 crystallites and relatively poor crystal quality limited
 the data quality somewhat and resulted in low I/sigma
 statistics. Two of the three ester groups were modelled
 as disordered over two orientations, with occupancies 
 determined by free variable refinement and then fixed to
 rounded values. DFIX, FLAT, ISOR and RIGU restraints were
 applied to these groups to maintain sensible chemical
 geometries and Uij tensors.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6A-C22
 1.4 with sigma of 0.02
 O9A-C32
 1.5 with sigma of 0.02
 C31-O9
 1.5 with sigma of 0.02
 N1-H1
 0.9 with sigma of 0.02
 N3-H3
 0.9 with sigma of 0.02
 H2-N2
 0.9 with sigma of 0.02
 H16A-H24B_$1
 2.2 with sigma of 0.02
3. Restrained planarity
 O9A, C30, O8A, C29
 with sigma of 0.1
 O9, C30, O8, C29
 with sigma of 0.1
 C21, C22, O5A, O6A
 with sigma of 0.1
 C21, C22, O5, O6
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O9A) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O8A) \\sim Ueq, Uanis(O8)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(C32) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O6A) \\sim Ueq, Uanis(O5A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C24) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C32, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O6A, C22, O5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: O5(0.85) O6(0.85) O8(0.75) O9(0.75) C23(0.85) H23A(0.85)
 H23B(0.85) H23C(0.85) C31(0.75) H31A(0.75) H31B(0.75) H31C(0.75) O8A(0.25)
 O9A(0.25) C32(0.25) H32A(0.25) H32B(0.25) H32C(0.25) O5A(0.15) O6A(0.15)
 C24(0.15) H24A(0.15) H24B(0.15) H24C(0.15)
7.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C17(H17A,H17B), C11(H11A,H11B), C13(H13A,
 H13B), C18(H18A,H18B), C14(H14A,H14B), C19(H19A,H19B), C20(H20A,H20B),
 C26(H26A,H26B), C21(H21A,H21B), C27(H27A,H27B), C25(H25A,H25B), C28(H28A,H28B),
  C29(H29A,H29B)
7.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C2(H2A)
7.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.4930(2) -0.1787(5) 0.37622(17) 0.0542(10) Uani 1 1 d . . . . .
O4 O 0.3842(2) 0.3192(5) 0.21737(17) 0.0518(10) Uani 1 1 d . . . . .
O2 O 0.7203(3) -0.9343(6) 0.56052(18) 0.0610(11) Uani 1 1 d . . . . .
O3 O 0.8308(3) -0.8348(6) 0.6297(2) 0.0662(12) Uani 1 1 d . . . . .
N2 N 0.4079(3) 0.5942(6) 0.2640(2) 0.0472(12) Uani 1 1 d D . . . .
O7 O 0.7371(3) 0.4384(7) 0.4784(2) 0.0778(15) Uani 1 1 d . . . . .
N1 N 0.5832(3) -0.1084(7) 0.4709(2) 0.0506(12) Uani 1 1 d D . . . .
N3 N 0.6995(3) 0.6585(7) 0.4050(2) 0.0548(13) Uani 1 1 d D . . . .
O5 O 0.1793(3) 1.4525(7) 0.2488(2) 0.0643(14) Uani 0.85 1 d . . P A 1
O6 O 0.0678(3) 1.3466(7) 0.2380(3) 0.0654(14) Uani 0.85 1 d . . P A 1
C8 C 0.4254(3) 0.4220(8) 0.2594(2) 0.0461(14) Uani 1 1 d . . . . .
C4 C 0.4933(3) 0.1768(8) 0.3336(2) 0.0455(13) Uani 1 1 d . . . . .
H4 H 0.4508 0.1016 0.3122 0.055 Uiso 1 1 calc R . . . .
C1 C 0.6201(3) 0.3906(7) 0.3927(2) 0.0447(13) Uani 1 1 d . . . . .
C5 C 0.4960(3) 0.3520(7) 0.3116(2) 0.0434(13) Uani 1 1 d . . . . .
C7 C 0.5406(3) -0.0710(8) 0.4104(2) 0.0467(14) Uani 1 1 d . . . . .
C6 C 0.5599(3) 0.4597(8) 0.3407(2) 0.0469(14) Uani 1 1 d . . . . .
H6 H 0.5623 0.5785 0.3254 0.056 Uiso 1 1 calc R . . . .
C2 C 0.6151(3) 0.2187(7) 0.4151(2) 0.0443(13) Uani 1 1 d . . . . .
H2A H 0.6558 0.1732 0.4511 0.053 Uiso 1 1 calc R . . . .
C3 C 0.5518(3) 0.1118(7) 0.3861(2) 0.0434(13) Uani 1 1 d . . . . .
C15 C 0.7564(4) -0.8186(9) 0.5968(3) 0.0537(15) Uani 1 1 d . . . . .
C12 C 0.6146(4) -0.4564(8) 0.6003(2) 0.0519(15) Uani 1 1 d . . . . .
H12A H 0.5605 -0.4714 0.5893 0.062 Uiso 1 1 calc R . . . .
H12B H 0.6402 -0.4396 0.6462 0.062 Uiso 1 1 calc R . . . .
C10 C 0.5733(3) -0.2763(8) 0.4995(3) 0.0504(15) Uani 1 1 d . . . . .
H10A H 0.5833 -0.3823 0.4779 0.061 Uiso 1 1 calc R . . . .
H10B H 0.5208 -0.2848 0.4945 0.061 Uiso 1 1 calc R . . . .
C22 C 0.1323(4) 1.3311(9) 0.2372(3) 0.0618(16) Uani 1 1 d D U . . .
C17 C 0.3333(3) 0.6639(8) 0.2246(3) 0.0530(14) Uani 1 1 d . . . . .
H17A H 0.2951 0.5763 0.2252 0.064 Uiso 1 1 calc R . . . .
H17B H 0.3279 0.6746 0.1810 0.064 Uiso 1 1 calc R . . . .
C9 C 0.6904(4) 0.4980(9) 0.4286(3) 0.0562(16) Uani 1 1 d . . . . .
C11 C 0.6255(4) -0.2839(8) 0.5687(3) 0.0546(16) Uani 1 1 d . . . . .
H11A H 0.6166 -0.1756 0.5899 0.066 Uiso 1 1 calc R . . . .
H11B H 0.6781 -0.2787 0.5735 0.066 Uiso 1 1 calc R . . . .
C13 C 0.6438(3) -0.6316(8) 0.5829(3) 0.0514(14) Uani 1 1 d . . . . .
H13A H 0.6250 -0.7379 0.5983 0.062 Uiso 1 1 calc R . . . .
H13B H 0.6235 -0.6406 0.5368 0.062 Uiso 1 1 calc R . . . .
C18 C 0.3200(3) 0.8465(8) 0.2467(3) 0.0542(15) Uani 1 1 d . . . . .
H18A H 0.3515 0.9384 0.2382 0.065 Uiso 1 1 calc R . . . .
H18B H 0.3362 0.8413 0.2926 0.065 Uiso 1 1 calc R . . . .
C14 C 0.7278(4) -0.6409(8) 0.6094(3) 0.0569(16) Uani 1 1 d . . . . .
H14A H 0.7463 -0.5406 0.5913 0.068 Uiso 1 1 calc R . . . .
H14B H 0.7483 -0.6214 0.6552 0.068 Uiso 1 1 calc R . . . .
C19 C 0.2398(4) 0.9091(9) 0.2169(3) 0.0611(16) Uani 1 1 d . . . . .
H19A H 0.2077 0.8151 0.2237 0.073 Uiso 1 1 calc R . . . .
H19B H 0.2242 0.9210 0.1712 0.073 Uiso 1 1 calc R . . . .
C20 C 0.2277(4) 1.0896(8) 0.2424(3) 0.0594(16) Uani 1 1 d . . . . .
H20A H 0.2566 1.1856 0.2326 0.071 Uiso 1 1 calc R . . . .
H20B H 0.2470 1.0807 0.2885 0.071 Uiso 1 1 calc R . . . .
C30 C 0.9959(4) 1.3379(11) 0.4179(3) 0.070(2) Uani 1 1 d . . . . .
O8 O 1.0006(5) 1.2776(10) 0.3711(4) 0.097(3) Uani 0.75 1 d . U P B 1
C26 C 0.8052(4) 0.8538(10) 0.4121(3) 0.070(2) Uani 1 1 d . . . . .
H26A H 0.7733 0.8927 0.3687 0.085 Uiso 1 1 calc R . . . .
H26B H 0.8351 0.7480 0.4091 0.085 Uiso 1 1 calc R . . . .
C21 C 0.1462(4) 1.1447(9) 0.2160(3) 0.0683(18) Uani 1 1 d . . . . .
H21A H 0.1181 1.0522 0.2283 0.082 Uiso 1 1 calc R . . . .
H21B H 0.1261 1.1442 0.1698 0.082 Uiso 1 1 calc R . . . .
C16 C 0.8635(4) -1.0012(10) 0.6196(3) 0.077(2) Uani 1 1 d . . . . .
H16A H 0.9177 -0.9997 0.6452 0.115 Uiso 1 1 calc DGR . . . .
H16B H 0.8539 -1.0107 0.5753 0.115 Uiso 1 1 calc GR . . . .
H16C H 0.8413 -1.1063 0.6314 0.115 Uiso 1 1 calc GR . . . .
C27 C 0.8573(4) 1.0025(11) 0.4423(3) 0.080(2) Uani 1 1 d . . . . .
H27A H 0.8276 1.1011 0.4500 0.096 Uiso 1 1 calc R . . . .
H27B H 0.8922 0.9567 0.4838 0.096 Uiso 1 1 calc R . . . .
C25 C 0.7561(5) 0.7895(11) 0.4396(3) 0.085(2) Uani 1 1 d . . . . .
H25A H 0.7876 0.7350 0.4808 0.101 Uiso 1 1 calc R . . . .
H25B H 0.7307 0.8971 0.4475 0.101 Uiso 1 1 calc R . . . .
C28 C 0.9031(4) 1.0890(11) 0.4145(3) 0.080(2) Uani 1 1 d . . . . .
H28A H 0.9357 0.9929 0.4096 0.096 Uiso 1 1 calc R . . . .
H28B H 0.8688 1.1282 0.3719 0.096 Uiso 1 1 calc R . . . .
O9 O 1.0319(6) 1.4748(15) 0.4464(4) 0.127(4) Uani 0.75 1 d D U P B 1
C29 C 0.9502(5) 1.2424(12) 0.4441(3) 0.101(3) Uani 1 1 d . . . . .
H29A H 0.9849 1.2011 0.4863 0.121 Uiso 1 1 calc R . . . .
H29B H 0.9173 1.3358 0.4502 0.121 Uiso 1 1 calc R . . . .
C23 C 0.0518(5) 1.5220(12) 0.2564(4) 0.072(2) Uani 0.85 1 d . . P A 1
H23A H 0.0411 1.6091 0.2221 0.107 Uiso 0.85 1 calc GR . P A 1
H23B H 0.0952 1.5644 0.2933 0.107 Uiso 0.85 1 calc GR . P A 1
H23C H 0.0083 1.5126 0.2665 0.107 Uiso 0.85 1 calc GR . P A 1
C31 C 1.0783(11) 1.569(3) 0.4190(9) 0.123(9) Uani 0.75 1 d D U P B 1
H31A H 1.0454 1.6320 0.3804 0.185 Uiso 0.75 1 calc GR . P B 1
H31B H 1.1091 1.4795 0.4095 0.185 Uiso 0.75 1 calc GR . P B 1
H31C H 1.1108 1.6590 0.4489 0.185 Uiso 0.75 1 calc GR . P B 1
O8A O 0.9557(17) 1.472(3) 0.3964(14) 0.121(9) Uani 0.25 1 d . U P B 2
O9A O 1.0613(14) 1.348(4) 0.4331(13) 0.097(8) Uani 0.25 1 d D U P B 2
C32 C 1.094(3) 1.532(5) 0.432(3) 0.075(14) Uani 0.25 1 d D U P B 2
H32A H 1.0737 1.5780 0.3891 0.112 Uiso 0.25 1 calc GR . P B 2
H32B H 1.1486 1.5217 0.4482 0.112 Uiso 0.25 1 calc GR . P B 2
H32C H 1.0810 1.6165 0.4584 0.112 Uiso 0.25 1 calc GR . P B 2
O5A O 0.137(2) 1.340(5) 0.2971(15) 0.093(8) Uani 0.15 1 d . U P A 2
O6A O 0.099(2) 1.502(3) 0.2136(15) 0.102(8) Uani 0.15 1 d D U P A 2
C24 C 0.048(3) 1.632(7) 0.232(2) 0.071(13) Uani 0.15 1 d . U P A 2
H24A H 0.0788 1.6934 0.2713 0.107 Uiso 0.15 1 calc GR . P A 2
H24B H 0.0089 1.5603 0.2367 0.107 Uiso 0.15 1 calc DGR . P A 2
H24C H 0.0255 1.7233 0.1988 0.107 Uiso 0.15 1 calc GR . P A 2
H2 H 0.435(3) 0.676(6) 0.2931(19) 0.044(16) Uiso 1 1 d D . . . .
H3 H 0.661(2) 0.686(9) 0.3699(17) 0.059(19) Uiso 1 1 d D . . . .
H1 H 0.609(3) -0.015(6) 0.493(3) 0.07(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.230(7) . ?
O4 C8 1.237(7) . ?
O2 C15 1.201(7) . ?
O3 C15 1.343(7) . ?
O3 C16 1.442(8) . ?
N2 C8 1.322(7) . ?
N2 C17 1.461(7) . ?
N2 H2 0.90(2) . ?
O7 C9 1.228(8) . ?
N1 C7 1.344(7) . ?
N1 C10 1.452(7) . ?
N1 H1 0.88(2) . ?
N3 C9 1.342(8) . ?
N3 C25 1.435(9) . ?
N3 H3 0.88(2) . ?
O5 C22 1.226(8) . ?
O6 C22 1.281(8) . ?
O6 C23 1.429(9) . ?
C8 C5 1.508(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(8) . ?
C4 C3 1.374(8) . ?
C1 C6 1.394(8) . ?
C1 C2 1.383(7) . ?
C1 C9 1.505(8) . ?
C5 C6 1.395(8) . ?
C7 C3 1.507(8) . ?
C6 H6 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(8) . ?
C15 C14 1.494(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.524(8) . ?
C12 C13 1.527(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(8) . ?
C22 C21 1.515(9) . ?
C22 O5A 1.37(3) . ?
C22 O6A 1.413(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.495(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.503(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.502(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.510(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.510(9) . ?
C30 O8 1.224(9) . ?
C30 O9 1.248(10) . ?
C30 C29 1.460(10) . ?
C30 O8A 1.23(3) . ?
C30 O9A 1.18(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.460(9) . ?
C26 C25 1.446(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.456(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.436(10) . ?
O9 C31 1.486(13) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O9A C32 1.49(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O6A C24 1.56(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C15 O3 C16 115.6(5) . . ?
C8 N2 C17 120.5(5) . . ?
C8 N2 H2 127(4) . . ?
C17 N2 H2 112(4) . . ?
C7 N1 C10 121.2(5) . . ?
C7 N1 H1 114(4) . . ?
C10 N1 H1 123(4) . . ?
C9 N3 C25 123.6(6) . . ?
C9 N3 H3 113(4) . . ?
C25 N3 H3 122(4) . . ?
C22 O6 C23 115.2(6) . . ?
O4 C8 N2 122.6(6) . . ?
O4 C8 C5 121.2(5) . . ?
N2 C8 C5 116.0(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C6 C1 C9 123.2(5) . . ?
C2 C1 C6 119.7(5) . . ?
C2 C1 C9 117.1(5) . . ?
C4 C5 C8 116.8(5) . . ?
C4 C5 C6 120.2(5) . . ?
C6 C5 C8 122.8(5) . . ?
O1 C7 N1 122.0(5) . . ?
O1 C7 C3 120.7(5) . . ?
N1 C7 C3 117.2(5) . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C1 C2 H2A 119.4 . . ?
C1 C2 C3 121.1(5) . . ?
C3 C2 H2A 119.4 . . ?
C4 C3 C7 116.7(5) . . ?
C4 C3 C2 119.4(5) . . ?
C2 C3 C7 123.8(5) . . ?
O2 C15 O3 121.7(6) . . ?
O2 C15 C14 126.5(6) . . ?
O3 C15 C14 111.8(5) . . ?
H12A C12 H12B 107.5 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C11 C12 C13 114.8(4) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
N1 C10 C11 111.5(5) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
O5 C22 O6 126.1(7) . . ?
O5 C22 C21 120.3(6) . . ?
O6 C22 C21 113.5(6) . . ?
O5A C22 C21 115.9(16) . . ?
O5A C22 O6A 100(2) . . ?
O6A C22 C21 141.7(15) . . ?
N2 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
N2 C17 C18 111.5(5) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
O7 C9 N3 122.0(6) . . ?
O7 C9 C1 119.7(5) . . ?
N3 C9 C1 118.3(6) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 C12 112.5(5) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.4(5) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.2(5) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C15 C14 C13 113.3(5) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 112.8(6) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C19 C20 C21 112.7(6) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
O8 C30 O9 122.3(7) . . ?
O8 C30 C29 119.8(8) . . ?
O9 C30 C29 117.9(7) . . ?
O8A C30 C29 98.9(14) . . ?
O9A C30 C29 133.1(13) . . ?
O9A C30 O8A 120.1(19) . . ?
H26A C26 H26B 107.0 . . ?
C27 C26 H26A 107.5 . . ?
C27 C26 H26B 107.5 . . ?
C25 C26 H26A 107.5 . . ?
C25 C26 H26B 107.5 . . ?
C25 C26 C27 119.2(6) . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C20 C21 C22 114.2(6) . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C27 H27A 106.6 . . ?
C26 C27 H27B 106.6 . . ?
H27A C27 H27B 106.6 . . ?
C28 C27 C26 122.9(6) . . ?
C28 C27 H27A 106.6 . . ?
C28 C27 H27B 106.6 . . ?
N3 C25 C26 117.7(6) . . ?
N3 C25 H25A 107.9 . . ?
N3 C25 H25B 107.9 . . ?
C26 C25 H25A 107.9 . . ?
C26 C25 H25B 107.9 . . ?
H25A C25 H25B 107.2 . . ?
C27 C28 H28A 107.1 . . ?
C27 C28 H28B 107.1 . . ?
H28A C28 H28B 106.8 . . ?
C29 C28 C27 121.0(7) . . ?
C29 C28 H28A 107.1 . . ?
C29 C28 H28B 107.1 . . ?
C30 O9 C31 116.9(10) . . ?
C30 C29 H29A 106.4 . . ?
C30 C29 H29B 106.4 . . ?
C28 C29 C30 123.7(7) . . ?
C28 C29 H29A 106.4 . . ?
C28 C29 H29B 106.4 . . ?
H29A C29 H29B 106.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O9 C31 H31A 109.5 . . ?
O9 C31 H31B 109.5 . . ?
O9 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 O9A C32 118(3) . . ?
O9A C32 H32A 109.5 . . ?
O9A C32 H32B 109.5 . . ?
O9A C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C22 O6A C24 133(3) . . ?
O6A C24 H24A 109.5 . . ?
O6A C24 H24B 109.5 . . ?
O6A C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C7 C3 C4 20.9(7) . . . . ?
O1 C7 C3 C2 -162.4(5) . . . . ?
O4 C8 C5 C4 -37.0(6) . . . . ?
O4 C8 C5 C6 148.0(5) . . . . ?
O2 C15 C14 C13 13.2(8) . . . . ?
O3 C15 C14 C13 -169.5(5) . . . . ?
N2 C8 C5 C4 138.3(5) . . . . ?
N2 C8 C5 C6 -36.7(6) . . . . ?
N2 C17 C18 C19 -168.3(5) . . . . ?
N1 C7 C3 C4 -157.7(5) . . . . ?
N1 C7 C3 C2 18.9(8) . . . . ?
N1 C10 C11 C12 178.3(5) . . . . ?
O5 C22 C21 C20 31.1(9) . . . . ?
O6 C22 C21 C20 -152.1(6) . . . . ?
C8 N2 C17 C18 167.5(5) . . . . ?
C8 C5 C6 C1 173.6(4) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C1 C2 C3 C7 -175.7(5) . . . . ?
C5 C4 C3 C7 173.6(4) . . . . ?
C5 C4 C3 C2 -3.2(7) . . . . ?
C7 N1 C10 C11 -177.5(5) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
C6 C1 C9 O7 170.7(6) . . . . ?
C6 C1 C9 N3 -8.5(8) . . . . ?
C2 C1 C6 C5 -1.1(7) . . . . ?
C2 C1 C9 O7 -6.4(8) . . . . ?
C2 C1 C9 N3 174.5(5) . . . . ?
C3 C4 C5 C8 -171.7(4) . . . . ?
C3 C4 C5 C6 3.4(7) . . . . ?
C12 C13 C14 C15 175.3(5) . . . . ?
C10 N1 C7 O1 -2.3(9) . . . . ?
C10 N1 C7 C3 176.3(5) . . . . ?
C17 N2 C8 O4 9.2(7) . . . . ?
C17 N2 C8 C5 -166.0(4) . . . . ?
C17 C18 C19 C20 177.3(5) . . . . ?
C9 N3 C25 C26 126.7(8) . . . . ?
C9 C1 C6 C5 -178.1(5) . . . . ?
C9 C1 C2 C3 178.5(5) . . . . ?
C11 C12 C13 C14 70.4(7) . . . . ?
C13 C12 C11 C10 72.3(7) . . . . ?
C18 C19 C20 C21 -175.5(5) . . . . ?
C19 C20 C21 C22 -176.0(5) . . . . ?
O8 C30 O9 C31 3(2) . . . . ?
O8 C30 C29 C28 -6.7(14) . . . . ?
C26 C27 C28 C29 176.1(8) . . . . ?
C21 C22 O6A C24 136(4) . . . . ?
C16 O3 C15 O2 -1.4(8) . . . . ?
C16 O3 C15 C14 -178.9(5) . . . . ?
C27 C26 C25 N3 172.8(7) . . . . ?
C27 C28 C29 C30 -178.4(8) . . . . ?
C25 N3 C9 O7 -11.6(10) . . . . ?
C25 N3 C9 C1 167.6(6) . . . . ?
C25 C26 C27 C28 -173.3(8) . . . . ?
O9 C30 C29 C28 176.8(11) . . . . ?
C29 C30 O9 C31 179.8(13) . . . . ?
C29 C30 O9A C32 -135(3) . . . . ?
C23 O6 C22 O5 -2.2(10) . . . . ?
C23 O6 C22 C21 -178.7(6) . . . . ?
O8A C30 C29 C28 101.7(18) . . . . ?
O8A C30 O9A C32 7(4) . . . . ?
O9A C30 C29 C28 -111(2) . . . . ?
O5A C22 C21 C20 -76(2) . . . . ?
O5A C22 O6A C24 -25(5) . . . . ?
O6A C22 C21 C20 124(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1503994'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H33 N3 O9, 5(H2 O)'
_chemical_formula_sum            'C24 H43 N3 O14'
_chemical_formula_weight         597.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   24.6517(13)
_cell_length_b                   4.7182(3)
_cell_length_c                   25.6558(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.827(4)
_cell_angle_gamma                90
_cell_volume                     2962.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.35
_cell_measurement_theta_min      2.647
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8477.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26640
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.366
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4178
_reflns_number_total             5443
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5443
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.026
_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)+(0.0540P)²+1.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1547
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 H10D-H11D
 2.2 with sigma of 0.02
 H2-N2
 0.91 with sigma of 0.02
 N3-H3A
 0.91 with sigma of 0.02
 H1-N1
 0.91 with sigma of 0.02
 O9-H9
 0.91 with sigma of 0.02
 H6-O6
 0.91 with sigma of 0.02
 H3-O3
 0.91 with sigma of 0.02
 O14-H14C = O14-H14D
 0.91 with sigma of 0.02
 O13-H13A = O13-H13B
 0.91 with sigma of 0.02
 O12-H12A = O12-H12B
 0.91 with sigma of 0.02
 O11-H11C = O11-H11D
 0.91 with sigma of 0.02
 O10-H10C = O10-H10D
 0.91 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B),
  C22(H22A,H22B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3B), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.54530(7) 0.2843(4) 0.11897(7) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.31889(8) 1.0190(5) 0.10580(8) 0.0425(5) Uani 1 1 d . . . . .
O3 O 0.25942(8) 1.1419(4) 0.03781(7) 0.0341(4) Uani 1 1 d D . . . .
H3 H 0.2421(14) 1.237(7) 0.0631(12) 0.051 Uiso 1 1 d DR . . . .
O4 O 0.41845(7) 0.7727(4) 0.30382(7) 0.0279(4) Uani 1 1 d . . . . .
O5 O 0.43021(7) 0.5586(3) 0.55995(6) 0.0247(4) Uani 1 1 d . . . . .
O6 O 0.34469(7) 0.4300(4) 0.57064(7) 0.0270(4) Uani 1 1 d D . . . .
H6 H 0.3612(12) 0.327(6) 0.5967(10) 0.041 Uiso 1 1 d DR . . . .
O7 O 0.60804(7) -0.0855(3) 0.35698(6) 0.0236(4) Uani 1 1 d . . . . .
O8 O 0.85745(8) -0.2284(4) 0.32935(7) 0.0336(4) Uani 1 1 d . . . . .
O9 O 0.87920(7) -0.0431(4) 0.40913(7) 0.0282(4) Uani 1 1 d D . . . .
H9 H 0.9025(12) 0.067(6) 0.3935(13) 0.042 Uiso 1 1 d DR . . . .
O11 O 0.35213(8) 1.4099(4) 0.23815(8) 0.0381(4) Uani 1 1 d D . . . .
H11C H 0.3774(13) 1.531(7) 0.2568(13) 0.057 Uiso 1 1 d DR . . . .
H11D H 0.3381(14) 1.289(6) 0.2606(12) 0.057 Uiso 1 1 d DR . . . .
O13 O 0.27067(9) 1.7269(5) 0.18252(9) 0.0445(5) Uani 1 1 d D . . . .
H13A H 0.2967(14) 1.615(8) 0.2043(14) 0.067 Uiso 1 1 d DR . . . .
H13B H 0.2918(15) 1.848(7) 0.1646(15) 0.067 Uiso 1 1 d DR . . . .
N1 N 0.48553(8) 0.6382(4) 0.12389(7) 0.0237(4) Uani 1 1 d D . . . .
H1 H 0.4695(11) 0.765(5) 0.1440(10) 0.028 Uiso 1 1 d DR . . . .
N2 N 0.48570(8) 0.7472(4) 0.37189(7) 0.0211(4) Uani 1 1 d D . . . .
H2 H 0.5192(8) 0.686(6) 0.3846(11) 0.025 Uiso 1 1 d DR . . . .
N3 N 0.63766(8) -0.2040(4) 0.27966(8) 0.0210(4) Uani 1 1 d D . . . .
H3A H 0.6348(11) -0.177(6) 0.2457(7) 0.025 Uiso 1 1 d DR . . . .
C1 C 0.56027(9) 0.2004(4) 0.22731(9) 0.0208(4) Uani 1 1 d . . . . .
H1A H 0.5817 0.0950 0.2057 0.025 Uiso 1 1 calc R . . . .
C2 C 0.56651(9) 0.1545(4) 0.28141(9) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.53545(9) 0.3116(5) 0.31300(9) 0.0195(4) Uani 1 1 d . . . . .
H3B H 0.5400 0.2834 0.3499 0.023 Uiso 1 1 calc R . . . .
C4 C 0.49792(9) 0.5093(4) 0.29075(9) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.49104(9) 0.5519(5) 0.23663(9) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.4647 0.6840 0.2214 0.025 Uiso 1 1 calc R . . . .
C6 C 0.52303(9) 0.3992(5) 0.20482(9) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.51846(9) 0.4374(5) 0.14593(9) 0.0222(5) Uani 1 1 d . . . . .
C8 C 0.48131(10) 0.6916(5) 0.06737(9) 0.0263(5) Uani 1 1 d . . . . .
H8A H 0.4831 0.5089 0.0487 0.032 Uiso 1 1 calc R . . . .
H8B H 0.5128 0.8084 0.0597 0.032 Uiso 1 1 calc R . . . .
C9 C 0.42847(10) 0.8432(5) 0.04705(9) 0.0256(5) Uani 1 1 d . . . . .
H9A H 0.4317 0.9174 0.0115 0.031 Uiso 1 1 calc R . . . .
H9B H 0.4235 1.0070 0.0701 0.031 Uiso 1 1 calc R . . . .
C10 C 0.37797(10) 0.6535(5) 0.04466(10) 0.0297(5) Uani 1 1 d . . . . .
H10A H 0.3836 0.4853 0.0229 0.036 Uiso 1 1 calc R . . . .
H10B H 0.3739 0.5861 0.0805 0.036 Uiso 1 1 calc R . . . .
C11 C 0.32545(10) 0.8016(5) 0.02211(10) 0.0300(5) Uani 1 1 d . . . . .
H11A H 0.3328 0.9119 -0.0091 0.036 Uiso 1 1 calc R . . . .
H11B H 0.2979 0.6555 0.0102 0.036 Uiso 1 1 calc R . . . .
C12 C 0.30170(10) 0.9963(5) 0.05947(10) 0.0288(5) Uani 1 1 d . . . . .
C13 C 0.46407(9) 0.6851(5) 0.32339(9) 0.0215(5) Uani 1 1 d . . . . .
C14 C 0.45793(9) 0.9248(5) 0.40718(9) 0.0221(5) Uani 1 1 d . . . . .
H14A H 0.4354 1.0679 0.3863 0.026 Uiso 1 1 calc R . . . .
H14B H 0.4856 1.0268 0.4314 0.026 Uiso 1 1 calc R . . . .
C15 C 0.42152(9) 0.7516(5) 0.43911(9) 0.0229(5) Uani 1 1 d . . . . .
H15A H 0.4438 0.6060 0.4595 0.027 Uiso 1 1 calc R . . . .
H15B H 0.3933 0.6530 0.4150 0.027 Uiso 1 1 calc R . . . .
C16 C 0.39376(10) 0.9400(5) 0.47658(9) 0.0238(5) Uani 1 1 d . . . . .
H16A H 0.4221 1.0296 0.5018 0.029 Uiso 1 1 calc R . . . .
H16B H 0.3736 1.0930 0.4562 0.029 Uiso 1 1 calc R . . . .
C17 C 0.35427(9) 0.7778(5) 0.50691(9) 0.0232(5) Uani 1 1 d . . . . .
H17A H 0.3319 0.9160 0.5240 0.028 Uiso 1 1 calc R . . . .
H17B H 0.3292 0.6665 0.4817 0.028 Uiso 1 1 calc R . . . .
C18 C 0.38110(9) 0.5814(5) 0.54790(9) 0.0210(5) Uani 1 1 d . . . . .
C19 C 0.60570(9) -0.0556(4) 0.30862(9) 0.0190(4) Uani 1 1 d . . . . .
C20 C 0.67678(9) -0.4150(5) 0.30277(9) 0.0219(5) Uani 1 1 d . . . . .
H20A H 0.6880 -0.5362 0.2744 0.026 Uiso 1 1 calc R . . . .
H20B H 0.6585 -0.5379 0.3267 0.026 Uiso 1 1 calc R . . . .
C21 C 0.72754(9) -0.2854(5) 0.33317(9) 0.0229(5) Uani 1 1 d . . . . .
H21A H 0.7164 -0.1510 0.3596 0.027 Uiso 1 1 calc R . . . .
H21B H 0.7479 -0.1777 0.3087 0.027 Uiso 1 1 calc R . . . .
C22 C 0.76494(9) -0.5119(5) 0.36088(9) 0.0230(5) Uani 1 1 d . . . . .
H22A H 0.7427 -0.6445 0.3794 0.028 Uiso 1 1 calc R . . . .
H22B H 0.7820 -0.6216 0.3342 0.028 Uiso 1 1 calc R . . . .
C23 C 0.80952(9) -0.3881(5) 0.40006(9) 0.0233(5) Uani 1 1 d . . . . .
H23A H 0.7924 -0.2687 0.4253 0.028 Uiso 1 1 calc R . . . .
H23B H 0.8289 -0.5450 0.4200 0.028 Uiso 1 1 calc R . . . .
C24 C 0.85066(9) -0.2120(5) 0.37530(9) 0.0220(5) Uani 1 1 d . . . . .
O12 O 0.41353(8) 1.0376(4) 0.17353(8) 0.0360(4) Uani 1 1 d D . . . .
H12A H 0.3999(15) 1.167(6) 0.1944(13) 0.054 Uiso 1 1 d DR . . . .
H12B H 0.3817(10) 1.013(8) 0.1509(12) 0.054 Uiso 1 1 d DR . . . .
O14 O 0.21000(8) 1.3992(4) 0.10726(8) 0.0359(4) Uani 1 1 d D . . . .
H14C H 0.2315(13) 1.511(7) 0.1295(12) 0.054 Uiso 1 1 d DR . . . .
H14D H 0.1954(14) 1.273(6) 0.1295(13) 0.054 Uiso 1 1 d DR . . . .
O10 O 0.32426(8) 1.0490(4) 0.31768(8) 0.0404(5) Uani 1 1 d D . . . .
H10C H 0.2971(13) 0.910(7) 0.3133(16) 0.061 Uiso 1 1 d DR . . . .
H10D H 0.3580(10) 0.961(7) 0.3198(13) 0.061 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.244(3) . ?
O2 C12 1.218(3) . ?
O3 H3 0.933(18) . ?
O3 C12 1.315(3) . ?
O4 C13 1.246(3) . ?
O5 C18 1.218(3) . ?
O6 H6 0.888(18) . ?
O6 C18 1.334(3) . ?
O7 C19 1.243(3) . ?
O8 C24 1.213(3) . ?
O9 H9 0.904(18) . ?
O9 C24 1.318(3) . ?
O11 H11C 0.934(19) . ?
O11 H11D 0.908(18) . ?
O13 H13A 0.957(19) . ?
O13 H13B 0.931(19) . ?
N1 H1 0.911(17) . ?
N1 C7 1.329(3) . ?
N1 C8 1.463(3) . ?
N2 H2 0.898(17) . ?
N2 C13 1.327(3) . ?
N2 C14 1.462(3) . ?
N3 H3A 0.875(17) . ?
N3 C19 1.342(3) . ?
N3 C20 1.462(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.395(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.393(3) . ?
C2 C19 1.498(3) . ?
C3 H3B 0.9500 . ?
C3 C4 1.388(3) . ?
C4 C5 1.393(3) . ?
C4 C13 1.501(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.496(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.523(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.496(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.522(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.530(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.508(3) . ?
O12 H12A 0.902(18) . ?
O12 H12B 0.927(19) . ?
O14 H14C 0.902(19) . ?
O14 H14D 0.924(18) . ?
O10 H10C 0.932(19) . ?
O10 H10D 0.925(18) . ?

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
C12 O3 H3 111(2) . . ?
C18 O6 H6 111(2) . . ?
C24 O9 H9 112(2) . . ?
H11C O11 H11D 110(3) . . ?
H13A O13 H13B 105(3) . . ?
C7 N1 H1 120.8(19) . . ?
C7 N1 C8 120.79(19) . . ?
C8 N1 H1 117.6(19) . . ?
C13 N2 H2 121.4(18) . . ?
C13 N2 C14 122.8(2) . . ?
C14 N2 H2 115.8(18) . . ?
C19 N3 H3A 119.3(18) . . ?
C19 N3 C20 122.21(19) . . ?
C20 N3 H3A 118.4(18) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C6 C1 C2 120.5(2) . . ?
C1 C2 C19 123.72(19) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 C19 116.7(2) . . ?
C2 C3 H3B 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3B 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 C13 122.0(2) . . ?
C5 C4 C13 117.8(2) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 C7 117.55(19) . . ?
C5 C6 C7 122.7(2) . . ?
O1 C7 N1 121.1(2) . . ?
O1 C7 C6 120.3(2) . . ?
N1 C7 C6 118.62(19) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.16(18) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.5(2) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.4(2) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.7(2) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
O2 C12 O3 122.2(2) . . ?
O2 C12 C11 124.2(2) . . ?
O3 C12 C11 113.6(2) . . ?
O4 C13 N2 123.2(2) . . ?
O4 C13 C4 119.6(2) . . ?
N2 C13 C4 117.2(2) . . ?
N2 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
N2 C14 C15 112.01(18) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.26(18) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.97(18) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C16 114.49(19) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
O5 C18 O6 122.8(2) . . ?
O5 C18 C17 125.2(2) . . ?
O6 C18 C17 112.01(19) . . ?
O7 C19 N3 122.2(2) . . ?
O7 C19 C2 119.41(19) . . ?
N3 C19 C2 118.41(19) . . ?
N3 C20 H20A 108.9 . . ?
N3 C20 H20B 108.9 . . ?
N3 C20 C21 113.37(18) . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C20 C21 C22 111.76(18) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 112.85(19) . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.82(19) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
O8 C24 O9 123.6(2) . . ?
O8 C24 C23 123.5(2) . . ?
O9 C24 C23 112.88(19) . . ?
H12A O12 H12B 96(3) . . ?
H14C O14 H14D 103(3) . . ?
H10C O10 H10D 109(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O14 0.933(18) 1.645(19) 2.579(3) 178(4) .
O6 H6 O7 0.888(18) 1.751(19) 2.633(2) 173(3) 3_656
O9 H9 O1 0.904(18) 1.70(2) 2.586(2) 164(3) 2_655
O11 H11C O4 0.934(19) 1.87(2) 2.791(3) 169(3) 1_565
O11 H11D O10 0.908(18) 1.914(19) 2.805(3) 167(3) .
O13 H13A O11 0.957(19) 1.81(2) 2.762(3) 172(4) .
O13 H13B O2 0.931(19) 1.90(2) 2.783(3) 157(4) 1_565
N1 H1 O12 0.911(17) 2.093(19) 2.976(3) 163(3) .
N2 H2 O5 0.898(17) 2.12(2) 2.928(3) 149(2) 3_666
N3 H3A O8 0.875(17) 1.973(19) 2.816(3) 161(3) 2_655
O12 H12A O11 0.902(18) 2.07(2) 2.953(3) 167(3) .
O12 H12B O2 0.927(19) 1.82(2) 2.740(3) 172(4) .
O14 H14C O13 0.902(19) 1.87(2) 2.769(3) 172(3) .
O14 H14D O10 0.924(18) 1.83(2) 2.746(3) 170(4) 2
O10 H10C O13 0.932(19) 1.90(2) 2.790(3) 160(4) 2_545
O10 H10D O4 0.925(18) 1.82(2) 2.723(2) 163(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
N1 C8 C9 C10 -72.9(3) . . . . ?
N2 C14 C15 C16 178.8(2) . . . . ?
N3 C20 C21 C22 174.78(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C19 O7 -179.0(2) . . . . ?
C1 C2 C19 N3 1.6(3) . . . . ?
C1 C6 C7 O1 3.7(3) . . . . ?
C1 C6 C7 N1 -176.0(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C6 C7 -179.97(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C13 -179.3(2) . . . . ?
C3 C2 C19 O7 1.6(3) . . . . ?
C3 C2 C19 N3 -177.76(19) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C3 C4 C13 O4 -152.2(2) . . . . ?
C3 C4 C13 N2 30.0(3) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C5 C4 C13 O4 28.4(3) . . . . ?
C5 C4 C13 N2 -149.4(2) . . . . ?
C5 C6 C7 O1 -175.5(2) . . . . ?
C5 C6 C7 N1 4.9(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C1 C2 C19 180.0(2) . . . . ?
C7 N1 C8 C9 158.8(2) . . . . ?
C8 N1 C7 O1 -2.1(4) . . . . ?
C8 N1 C7 C6 177.5(2) . . . . ?
C8 C9 C10 C11 -177.5(2) . . . . ?
C9 C10 C11 C12 -78.0(3) . . . . ?
C10 C11 C12 O2 -6.8(4) . . . . ?
C10 C11 C12 O3 173.9(2) . . . . ?
C13 N2 C14 C15 89.0(3) . . . . ?
C13 C4 C5 C6 177.9(2) . . . . ?
C14 N2 C13 O4 0.1(3) . . . . ?
C14 N2 C13 C4 177.81(18) . . . . ?
C14 C15 C16 C17 176.5(2) . . . . ?
C15 C16 C17 C18 71.0(3) . . . . ?
C16 C17 C18 O5 4.7(3) . . . . ?
C16 C17 C18 O6 -175.51(18) . . . . ?
C19 N3 C20 C21 -74.8(3) . . . . ?
C19 C2 C3 C4 -179.55(19) . . . . ?
C20 N3 C19 O7 1.1(3) . . . . ?
C20 N3 C19 C2 -179.51(18) . . . . ?
C20 C21 C22 C23 -168.30(18) . . . . ?
C21 C22 C23 C24 -66.3(2) . . . . ?
C22 C23 C24 O8 -19.6(3) . . . . ?
C22 C23 C24 O9 161.83(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1503993'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C54 H78 N6 O18)'
_chemical_formula_sum            'C27 H39 N3 O9'
_chemical_formula_weight         549.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'

_cell_length_a                   15.5682(6)
_cell_length_b                   15.5682(6)
_cell_length_c                   6.8268(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1432.93(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.96
_cell_measurement_theta_min      3.28
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8202.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.315
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                832
_reflns_number_total             956
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         956
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+0.6980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          
;
The structure model presents an averaged description of the total structure, with
both orientations of columnar hydrogen bonding overlapped, with a perpendicular
oriented mirror plane. Multiple attempts were made to index a larger unit cell in 
which the orientation of these stacks was resolved, but all resulted in equivalent
disorder with reduced data/parameter ratio and poor institial reflections. The 
model is presented as the most appropriate description of the crystal as a whole.
All atoms could be located from the Fourier residuals, and PART -1 cards were used 
to prevent unreasonable bonding outside the asymmetric unit.
;
_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. Restrained distances
 N1-H1A
 0.91 with sigma of 0.02
3. Others
 Fixed Sof: N1(0.5) H1A(0.5) O1(0.5) O2(0.5) O3(0.5) C4(0.5) H4A(0.5) H4B(0.5)
 C5(0.5) H5A(0.5) H5B(0.5) C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5)
 C8(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.09949(19) 1.07341(19) 0.2500 0.0259(6) Uani 1 2 d S T P . .
H1 H 0.1674 1.1237 0.2500 0.031 Uiso 1 2 calc RS T P . .
N1 N 0.2308(2) 0.9965(2) 0.3456(4) 0.0243(7) Uani 0.5 1 d D . . A -1
H1A H 0.233(3) 1.045(2) 0.422(5) 0.029 Uiso 0.5 1 d DR . . B -1
O1 O 0.13710(19) 0.86867(19) 0.1430(4) 0.0289(7) Uani 0.5 1 d . . . A -1
C2 C 0.07407(18) 0.97429(18) 0.2500 0.0251(6) Uani 1 2 d S T P A .
O2 O 0.4818(3) 0.8240(3) 0.8479(5) 0.0565(10) Uani 0.5 1 d . . . A -1
C3 C 0.15075(19) 0.94229(18) 0.2500 0.0251(6) Uani 1 2 d S T P . .
O3 O 0.4361(2) 0.8492(2) 1.1465(4) 0.0389(8) Uani 0.5 1 d . . . A -1
C4 C 0.3046(3) 0.9670(3) 0.3873(5) 0.0258(8) Uani 0.5 1 d . . . A -1
H4A H 0.3721 1.0251 0.3739 0.031 Uiso 0.5 1 calc R . . A -1
H4B H 0.2977 0.9160 0.2918 0.031 Uiso 0.5 1 calc R . . A -1
C5 C 0.2904(3) 0.9251(3) 0.5958(5) 0.0279(8) Uani 0.5 1 d . . . A -1
H5A H 0.2900 0.9738 0.6884 0.033 Uiso 0.5 1 calc R . . A -1
H5B H 0.2249 0.8639 0.6040 0.033 Uiso 0.5 1 calc R . . A -1
C6 C 0.3701(7) 0.9012(6) 0.6598(14) 0.0247(15) Uani 0.5 1 d . . . A -1
H6A H 0.4366 0.9591 0.6345 0.030 Uiso 0.5 1 calc R . . A -1
H6B H 0.3639 0.8445 0.5825 0.030 Uiso 0.5 1 calc R . . A -1
C7 C 0.3595(9) 0.8754(8) 0.8777(16) 0.038(2) Uani 0.5 1 d . . . A -1
H7A H 0.3685 0.9335 0.9539 0.046 Uiso 0.5 1 calc R . . A -1
H7B H 0.2915 0.8201 0.9027 0.046 Uiso 0.5 1 calc R . . A -1
C8 C 0.4322(3) 0.8465(3) 0.9477(6) 0.0376(10) Uani 0.5 1 d . . . A -1
C9 C 0.5014(4) 0.8193(3) 1.263(2) 0.0541(18) Uani 0.5 1 d . . . A -1
H9A H 0.5683 0.8519 1.2064 0.081 Uiso 0.5 1 calc GR . . A -1
H9B H 0.4728 0.7472 1.2563 0.081 Uiso 0.5 1 calc GR . . A -1
H9C H 0.5049 0.8396 1.3997 0.081 Uiso 0.5 1 calc GR . . A -1


_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
C1 H1 0.9500 . ?
C1 C2 1.388(4) . ?
C1 C2 1.400(4) 2_675 ?
N1 H1A 0.912(19) . ?
N1 C3 1.281(4) . ?
N1 C4 1.463(4) . ?
O1 C3 1.284(3) . ?
C2 C1 1.400(4) 3_465 ?
C2 C3 1.506(3) . ?
O2 C8 1.205(5) . ?
O3 C8 1.358(5) . ?
O3 C9 1.534(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.535(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.527(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.528(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.490(12) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C2 C1 H1 119.8 . . ?
C2 C1 H1 119.8 2_675 . ?
C2 C1 C2 120.4(3) . 2_675 ?
C3 N1 H1A 117(3) . . ?
C3 N1 C4 123.4(3) . . ?
C4 N1 H1A 117(3) . . ?
C1 C2 C1 119.6(3) . 3_465 ?
C1 C2 C3 118.1(2) 3_465 . ?
C1 C2 C3 122.4(2) . . ?
N1 C3 O1 123.4(3) . . ?
N1 C3 C2 117.0(2) . . ?
O1 C3 C2 119.4(2) . . ?
C8 O3 C9 122.3(5) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
N1 C4 C5 110.2(3) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 114.0(4) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.4(9) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 113.2(11) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O2 C8 O3 123.3(4) . . ?
O2 C8 C7 126.8(6) . . ?
O3 C8 C7 109.9(6) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C2 C3 N1 34.86(18) . . . . ?
C1 C2 C3 N1 -145.14(18) 3_465 . . . ?
C1 C2 C3 O1 -139.24(19) . . . . ?
C1 C2 C3 O1 40.76(19) 3_465 . . . ?
N1 C4 C5 C6 -174.6(4) . . . . ?
C2 C1 C2 C1 0.0 2_675 . . 3_465 ?
C2 C1 C2 C3 180.0 2_675 . . . ?
C3 N1 C4 C5 -98.5(3) . . . . ?
C4 N1 C3 O1 -16.8(4) . . . . ?
C4 N1 C3 C2 169.3(2) . . . . ?
C4 C5 C6 C7 171.3(7) . . . . ?
C5 C6 C7 C8 177.2(5) . . . . ?
C6 C7 C8 O2 -15.0(13) . . . . ?
C6 C7 C8 O3 164.6(8) . . . . ?
C9 O3 C8 O2 -2.7(6) . . . . ?
C9 O3 C8 C7 177.6(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1503992'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H27 N3 O9'
_chemical_formula_sum            'C21 H27 N3 O9'
_chemical_formula_weight         465.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.9042(2)
_cell_length_b                   16.9098(6)
_cell_length_c                   17.0515(7)
_cell_angle_alpha                77.472(3)
_cell_angle_beta                 87.209(4)
_cell_angle_gamma                83.111(3)
_cell_volume                     1370.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.05
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8482.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10762
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.771
_diffrn_reflns_theta_max         66.771
_diffrn_reflns_theta_min         2.694
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             4771
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 The contents of the solvent channels could not be ascertained
 crystallographically from the Fourier residual peaks, and so
 the contents were determined by supporting methods.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N3-H3
 0.9 with sigma of 0.01
 N2-H2
 0.9 with sigma of 0.01
 N1-H1
 0.9 with sigma of 0.01
 O8-H8
 0.84 with sigma of 0.01
 O4-H4
 0.84 with sigma of 0.01
 O6-H6
 0.84 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,H19B), C14(H14A,
 H14B), C8(H8A,H8B), C9(H9A,H9B), C20(H20A,H20B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4A), C6(H6A)
;
_atom_sites_solution_hydrogens   mixed
_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 0.2456(4) 0.76067(10) 0.52051(12) 0.0379(5) Uani 1 1 d . . . . .
O6 O -0.3681(4) 0.63324(11) 0.26057(12) 0.0403(5) Uani 1 1 d D . . . .
O3 O 0.7002(4) 0.45508(10) 0.78770(12) 0.0391(5) Uani 1 1 d . . . . .
O7 O -0.1865(4) 0.53592(10) 0.36038(12) 0.0402(5) Uani 1 1 d . . . . .
O4 O 1.4117(4) 1.17211(11) 0.59118(14) 0.0416(5) Uani 1 1 d D . . . .
O5 O 1.2728(4) 1.09555(11) 0.51252(13) 0.0436(5) Uani 1 1 d . . . . .
O9 O 1.6668(4) 0.37546(11) 1.09573(12) 0.0428(5) Uani 1 1 d . . . . .
O1 O 1.0457(4) 0.81089(11) 0.77552(12) 0.0460(5) Uani 1 1 d . . . . .
N2 N 0.1776(4) 0.62880(12) 0.55365(14) 0.0332(5) Uani 1 1 d D . . . .
N3 N 1.0080(5) 0.50262(13) 0.85257(14) 0.0343(5) Uani 1 1 d D . . . .
O8 O 1.5839(5) 0.24579(12) 1.11754(15) 0.0606(7) Uani 1 1 d D . . . .
N1 N 0.9887(5) 0.86747(13) 0.64420(15) 0.0396(6) Uani 1 1 d D . . . .
C3 C 0.4977(5) 0.67886(15) 0.63115(16) 0.0325(6) Uani 1 1 d . . . . .
C12 C 0.2969(5) 0.69157(15) 0.56451(16) 0.0323(6) Uani 1 1 d . . . . .
C2 C 0.6232(5) 0.74588(15) 0.63932(16) 0.0331(6) Uani 1 1 d . . . . .
H2A H 0.5771 0.7971 0.6041 0.040 Uiso 1 1 calc R . . . .
C17 C 0.8190(5) 0.51338(15) 0.79647(16) 0.0324(6) Uani 1 1 d . . . . .
C1 C 0.8150(5) 0.73894(15) 0.69822(17) 0.0349(6) Uani 1 1 d . . . . .
C16 C -0.1976(5) 0.60473(15) 0.32075(16) 0.0332(6) Uani 1 1 d . . . . .
C13 C -0.0045(5) 0.63703(15) 0.48569(17) 0.0349(6) Uani 1 1 d . . . . .
H13A H -0.1345 0.6872 0.4821 0.042 Uiso 1 1 calc R . . . .
H13B H -0.1130 0.5900 0.4952 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5664(5) 0.60390(15) 0.68297(16) 0.0333(6) Uani 1 1 d . . . . .
H4A H 0.4818 0.5578 0.6775 0.040 Uiso 1 1 calc R . . . .
C5 C 0.7582(5) 0.59590(15) 0.74286(16) 0.0326(6) Uani 1 1 d . . . . .
C6 C 0.8784(5) 0.66379(15) 0.75079(16) 0.0342(6) Uani 1 1 d . . . . .
H6A H 1.0051 0.6592 0.7924 0.041 Uiso 1 1 calc R . . . .
C15 C -0.0244(5) 0.66805(15) 0.33391(17) 0.0354(6) Uani 1 1 d . . . . .
H15A H -0.1470 0.7174 0.3401 0.043 Uiso 1 1 calc R . . . .
H15B H 0.0935 0.6834 0.2855 0.043 Uiso 1 1 calc R . . . .
C7 C 0.9586(5) 0.80937(15) 0.70895(18) 0.0372(6) Uani 1 1 d . . . . .
C11 C 1.2584(6) 1.11782(15) 0.57539(18) 0.0381(7) Uani 1 1 d . . . . .
C18 C 1.0699(6) 0.42211(16) 0.90517(17) 0.0382(6) Uani 1 1 d . . . . .
H18A H 1.1368 0.3822 0.8719 0.046 Uiso 1 1 calc R . . . .
H18B H 0.8989 0.4048 0.9335 0.046 Uiso 1 1 calc R . . . .
C19 C 1.2829(6) 0.42115(16) 0.96643(17) 0.0373(6) Uani 1 1 d . . . . .
H19A H 1.2142 0.4584 1.0022 0.045 Uiso 1 1 calc R . . . .
H19B H 1.4536 0.4397 0.9390 0.045 Uiso 1 1 calc R . . . .
C14 C 0.1570(5) 0.64107(16) 0.40652(17) 0.0359(6) Uani 1 1 d . . . . .
H14A H 0.2962 0.6796 0.4031 0.043 Uiso 1 1 calc R . . . .
H14B H 0.2554 0.5866 0.4057 0.043 Uiso 1 1 calc R . . . .
C8 C 1.1301(6) 0.93910(15) 0.64427(19) 0.0404(7) Uani 1 1 d . . . . .
H8A H 1.2640 0.9466 0.5986 0.048 Uiso 1 1 calc R . . . .
H8B H 1.2326 0.9302 0.6946 0.048 Uiso 1 1 calc R . . . .
C9 C 0.9254(6) 1.01596(15) 0.63732(19) 0.0419(7) Uani 1 1 d . . . . .
H9A H 0.8345 1.0275 0.5848 0.050 Uiso 1 1 calc R . . . .
H9B H 0.7820 1.0067 0.6802 0.050 Uiso 1 1 calc R . . . .
C21 C 1.5480(6) 0.32260(16) 1.07986(17) 0.0390(7) Uani 1 1 d . . . . .
C20 C 1.3411(7) 0.33480(17) 1.01521(19) 0.0477(8) Uani 1 1 d . . . . .
H20A H 1.1662 0.3170 1.0404 0.057 Uiso 1 1 calc R . . . .
H20B H 1.4059 0.2987 0.9779 0.057 Uiso 1 1 calc R . . . .
C10 C 1.0681(6) 1.08910(16) 0.64465(19) 0.0426(7) Uani 1 1 d . . . . .
H10A H 0.9263 1.1347 0.6497 0.051 Uiso 1 1 calc R . . . .
H10B H 1.1743 1.0747 0.6947 0.051 Uiso 1 1 calc R . . . .
H3 H 1.096(5) 0.5446(11) 0.8583(16) 0.030(7) Uiso 1 1 d D . . . .
H2 H 0.221(5) 0.5793(8) 0.5835(14) 0.031(7) Uiso 1 1 d D . . . .
H1 H 0.927(6) 0.8644(16) 0.5970(9) 0.037(8) Uiso 1 1 d D . . . .
H6 H -0.448(7) 0.5962(17) 0.249(2) 0.081(13) Uiso 1 1 d D . . . .
H4 H 1.514(6) 1.187(2) 0.5513(14) 0.067(13) Uiso 1 1 d D . . . .
H8 H 1.711(6) 0.237(2) 1.1511(19) 0.080(13) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C12 1.249(3) . ?
O6 C16 1.325(3) . ?
O6 H6 0.842(10) . ?
O3 C17 1.242(3) . ?
O7 C16 1.209(3) . ?
O4 C11 1.332(3) . ?
O4 H4 0.837(10) . ?
O5 C11 1.207(3) . ?
O9 C21 1.207(3) . ?
O1 C7 1.239(3) . ?
N2 C12 1.322(3) . ?
N2 C13 1.470(3) . ?
N2 H2 0.887(10) . ?
N3 C17 1.333(3) . ?
N3 C18 1.466(3) . ?
N3 H3 0.897(10) . ?
O8 C21 1.313(3) . ?
O8 H8 0.845(10) . ?
N1 C7 1.324(4) . ?
N1 C8 1.466(3) . ?
N1 H1 0.888(10) . ?
C3 C12 1.503(3) . ?
C3 C2 1.388(3) . ?
C3 C4 1.393(4) . ?
C2 H2A 0.9500 . ?
C2 C1 1.386(4) . ?
C17 C5 1.498(4) . ?
C1 C6 1.398(4) . ?
C1 C7 1.502(3) . ?
C16 C15 1.503(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.396(3) . ?
C5 C6 1.386(3) . ?
C6 H6A 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.516(3) . ?
C11 C10 1.501(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.509(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.517(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(3) . ?
C21 C20 1.499(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O6 H6 112(3) . . ?
C11 O4 H4 109(3) . . ?
C12 N2 C13 120.8(2) . . ?
C12 N2 H2 120.8(17) . . ?
C13 N2 H2 118.0(17) . . ?
C17 N3 C18 119.6(2) . . ?
C17 N3 H3 120.1(17) . . ?
C18 N3 H3 120.3(17) . . ?
C21 O8 H8 111(3) . . ?
C7 N1 C8 123.3(2) . . ?
C7 N1 H1 121.1(18) . . ?
C8 N1 H1 115.6(18) . . ?
C2 C3 C12 117.2(2) . . ?
C2 C3 C4 119.3(2) . . ?
C4 C3 C12 123.5(2) . . ?
O2 C12 N2 121.2(2) . . ?
O2 C12 C3 119.8(2) . . ?
N2 C12 C3 119.0(2) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2A 119.6 . . ?
O3 C17 N3 120.2(2) . . ?
O3 C17 C5 120.7(2) . . ?
N3 C17 C5 119.1(2) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C7 122.8(2) . . ?
C6 C1 C7 117.8(2) . . ?
O6 C16 C15 112.1(2) . . ?
O7 C16 O6 123.3(2) . . ?
O7 C16 C15 124.6(2) . . ?
N2 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
N2 C13 C14 111.7(2) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C3 C4 H4A 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C17 117.4(2) . . ?
C6 C5 C17 123.5(2) . . ?
C6 C5 C4 119.2(2) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6A 119.7 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C16 C15 C14 114.3(2) . . ?
H15A C15 H15B 107.6 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
O1 C7 N1 123.0(2) . . ?
O1 C7 C1 120.3(3) . . ?
N1 C7 C1 116.7(2) . . ?
O4 C11 C10 111.7(3) . . ?
O5 C11 O4 123.2(3) . . ?
O5 C11 C10 125.1(2) . . ?
N3 C18 H18A 109.0 . . ?
N3 C18 H18B 109.0 . . ?
N3 C18 C19 112.7(2) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
C18 C19 C20 108.6(2) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 C13 112.7(2) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.0(2) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.2(2) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
O9 C21 O8 124.0(3) . . ?
O9 C21 C20 125.3(3) . . ?
O8 C21 C20 110.7(2) . . ?
C19 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
C21 C20 C19 115.9(2) . . ?
C21 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C11 C10 C9 114.5(2) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O9 0.897(10) 2.175(12) 3.047(3) 164(2) 2_867
N2 H2 O7 0.887(10) 1.999(13) 2.849(3) 160(2) 2_566
N1 H1 O5 0.888(10) 2.092(14) 2.932(3) 157(2) 2_776
O6 H6 O3 0.842(10) 1.798(16) 2.609(2) 161(4) 2_566
O4 H4 O2 0.837(10) 1.818(14) 2.636(3) 165(4) 2_776
O8 H8 O1 0.845(10) 1.768(15) 2.586(3) 162(4) 2_867

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
O6 C16 C15 C14 175.0(2) . . . . ?
O3 C17 C5 C4 -0.5(4) . . . . ?
O3 C17 C5 C6 178.3(3) . . . . ?
O7 C16 C15 C14 -4.4(4) . . . . ?
O4 C11 C10 C9 -169.2(2) . . . . ?
O5 C11 C10 C9 11.1(4) . . . . ?
O9 C21 C20 C19 0.6(5) . . . . ?
N2 C13 C14 C15 -167.3(2) . . . . ?
N3 C17 C5 C4 177.7(3) . . . . ?
N3 C17 C5 C6 -3.4(4) . . . . ?
N3 C18 C19 C20 -177.6(2) . . . . ?
O8 C21 C20 C19 -179.4(3) . . . . ?
N1 C8 C9 C10 175.1(2) . . . . ?
C3 C2 C1 C6 -1.1(4) . . . . ?
C3 C2 C1 C7 179.3(3) . . . . ?
C3 C4 C5 C17 179.5(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C12 N2 C13 C14 74.3(3) . . . . ?
C12 C3 C2 C1 -178.7(2) . . . . ?
C12 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C12 O2 -1.4(4) . . . . ?
C2 C3 C12 N2 178.5(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C1 C6 C5 2.1(4) . . . . ?
C2 C1 C7 O1 153.6(3) . . . . ?
C2 C1 C7 N1 -27.3(4) . . . . ?
C17 N3 C18 C19 -178.5(3) . . . . ?
C17 C5 C6 C1 179.3(3) . . . . ?
C16 C15 C14 C13 -73.1(3) . . . . ?
C13 N2 C12 O2 4.4(4) . . . . ?
C13 N2 C12 C3 -175.5(2) . . . . ?
C4 C3 C12 O2 180.0(3) . . . . ?
C4 C3 C12 N2 -0.1(4) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C6 C1 C7 O1 -25.9(4) . . . . ?
C6 C1 C7 N1 153.1(3) . . . . ?
C7 N1 C8 C9 -107.7(3) . . . . ?
C7 C1 C6 C5 -178.4(3) . . . . ?
C18 N3 C17 O3 -1.5(4) . . . . ?
C18 N3 C17 C5 -179.8(2) . . . . ?
C18 C19 C20 C21 -179.5(3) . . . . ?
C8 N1 C7 O1 0.6(5) . . . . ?
C8 N1 C7 C1 -178.5(2) . . . . ?
C8 C9 C10 C11 68.4(3) . . . . ?

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