# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_q21f
_database_code_depnum_ccdc_archive 'CCDC 1974541'
loop_
_audit_author_name
_audit_author_address
'Victor Day'
;University of Kansas
United States of America
;
_audit_update_record             
;
2019-12-28 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N6 O9'
_chemical_formula_weight         446.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7091(6)
_cell_length_b                   24.6511(16)
_cell_length_c                   9.7352(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.492(3)
_cell_angle_gamma                90
_cell_volume                     2083.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      69.96

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    1.004
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23676
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.586
_diffrn_reflns_theta_max         70.069
_diffrn_reflns_theta_full        66.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3853
_reflns_number_gt                3395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²+1.6745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3853
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4728(2) 0.44121(6) 0.81866(16) 0.0386(4) Uani 1 1 d . . . . .
O2 O -0.01464(19) 0.44059(6) 0.21140(16) 0.0378(4) Uani 1 1 d . . . . .
O3 O -0.11759(16) 0.34195(6) 0.36257(16) 0.0321(4) Uani 1 1 d . . . . .
O4 O 0.57814(16) 0.34119(6) 0.67619(17) 0.0326(4) Uani 1 1 d . . . . .
O5 O 0.4769(2) 0.61970(6) 0.95018(16) 0.0339(4) Uani 1 1 d . . . . .
H5O H 0.513(3) 0.6060(11) 1.031(3) 0.039(7) Uiso 1 1 d . . . . .
O6 O 0.0487(2) 0.61366(6) 0.03185(16) 0.0405(4) Uani 1 1 d . . . . .
H6O H 0.021(3) 0.6012(11) -0.055(3) 0.048(8) Uiso 1 1 d . . . . .
O7 O 0.06010(17) 0.19358(6) 0.31139(18) 0.0340(4) Uani 1 1 d . . . . .
H7O H 0.039(4) 0.1713(13) 0.373(3) 0.057(9) Uiso 1 1 d . . . . .
O8 O 0.39428(17) 0.19070(6) 0.71751(18) 0.0323(4) Uani 1 1 d . . . . .
H8O H 0.416(4) 0.1690(13) 0.653(4) 0.061(9) Uiso 1 1 d . . . . .
N1 N 0.43774(19) 0.51417(6) 0.67922(18) 0.0221(4) Uani 1 1 d . . . . .
H1N H 0.392(3) 0.5264(9) 0.604(2) 0.020(5) Uiso 1 1 d . . . . .
N2 N 0.07855(19) 0.51612(6) 0.32032(17) 0.0222(4) Uani 1 1 d . . . . .
H2N H 0.138(3) 0.5271(10) 0.390(3) 0.027(6) Uiso 1 1 d . . . . .
N3 N 0.24258(16) 0.45681(6) 0.50784(14) 0.0171(3) Uani 1 1 d . . . . .
N4 N 0.0765(2) 0.30669(6) 0.24897(17) 0.0216(4) Uani 1 1 d . . . . .
H4N H 0.177(3) 0.3065(11) 0.241(3) 0.047(8) Uiso 1 1 d . . . . .
N5 N 0.37700(19) 0.30445(6) 0.77818(17) 0.0207(4) Uani 1 1 d . . . . .
H5N H 0.280(3) 0.3042(10) 0.782(3) 0.038(7) Uiso 1 1 d . . . . .
N8 N 0.22860(17) 0.34490(6) 0.51613(15) 0.0194(3) Uani 1 1 d . . . . .
C1 C 0.4213(2) 0.46224(7) 0.71087(19) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.3283(2) 0.42933(7) 0.60243(18) 0.0172(4) Uani 1 1 d . . . . .
C4 C 0.1495(2) 0.42973(7) 0.41721(18) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.0629(2) 0.46281(7) 0.30546(19) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.0192(2) 0.33952(7) 0.3397(2) 0.0204(4) Uani 1 1 d . . . . .
C7 C 0.1372(2) 0.37314(7) 0.42476(19) 0.0180(4) Uani 1 1 d . . . . .
C9 C 0.3264(2) 0.37232(7) 0.60332(19) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.4392(2) 0.33805(7) 0.6919(2) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.5153(2) 0.55249(7) 0.7753(2) 0.0255(4) Uani 1 1 d . . . . .
H11A H 0.569(3) 0.5810(11) 0.724(3) 0.041(7) Uiso 1 1 d . . . . .
H11B H 0.598(3) 0.5349(11) 0.832(3) 0.041(7) Uiso 1 1 d . . . . .
C12 C 0.4025(3) 0.57917(8) 0.8647(2) 0.0288(5) Uani 1 1 d . . . . .
H12A H 0.321(4) 0.5976(12) 0.802(3) 0.058(9) Uiso 1 1 d . . . . .
H12B H 0.361(3) 0.5517(11) 0.918(3) 0.045(7) Uiso 1 1 d . . . . .
C13 C 0.0063(2) 0.55447(8) 0.2213(2) 0.0259(4) Uani 1 1 d . . . . .
H13A H -0.026(3) 0.5868(11) 0.271(3) 0.036(6) Uiso 1 1 d . . . . .
H13B H -0.088(3) 0.5381(11) 0.177(3) 0.046(7) Uiso 1 1 d . . . . .
C14 C 0.1166(3) 0.57193(9) 0.1176(2) 0.0326(5) Uani 1 1 d . . . . .
H14A H 0.210(4) 0.5869(12) 0.169(3) 0.054(8) Uiso 1 1 d . . . . .
H14B H 0.143(3) 0.5400(12) 0.062(3) 0.054(8) Uiso 1 1 d . . . . .
C15 C -0.0204(3) 0.26821(8) 0.1669(2) 0.0269(4) Uani 1 1 d . . . . .
H15A H 0.048(3) 0.2545(10) 0.090(3) 0.034(6) Uiso 1 1 d . . . . .
H15B H -0.111(3) 0.2873(11) 0.123(3) 0.048(8) Uiso 1 1 d . . . . .
C16 C -0.0726(2) 0.22110(8) 0.2520(2) 0.0300(5) Uani 1 1 d . . . . .
H16A H -0.138(3) 0.2343(10) 0.326(3) 0.040(7) Uiso 1 1 d . . . . .
H16B H -0.131(3) 0.1967(12) 0.186(3) 0.052(8) Uiso 1 1 d . . . . .
C17 C 0.4702(2) 0.26582(7) 0.8628(2) 0.0250(4) Uani 1 1 d . . . . .
H17A H 0.399(3) 0.2544(9) 0.935(2) 0.026(6) Uiso 1 1 d . . . . .
H17B H 0.559(3) 0.2847(10) 0.907(3) 0.038(7) Uiso 1 1 d . . . . .
C18 C 0.5240(2) 0.21866(8) 0.7798(2) 0.0272(5) Uani 1 1 d . . . . .
H18A H 0.590(3) 0.2307(9) 0.711(2) 0.023(5) Uiso 1 1 d . . . . .
H18B H 0.585(3) 0.1937(11) 0.843(3) 0.043(7) Uiso 1 1 d . . . . .
O1W O 0.72236(18) 0.41236(6) 0.51380(15) 0.0283(3) Uani 1 1 d . . . . .
H1W1 H 0.784(3) 0.3918(13) 0.462(3) 0.052(8) Uiso 1 1 d . . . . .
H1W2 H 0.673(3) 0.3892(12) 0.568(3) 0.051(8) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.224(2) . ?
O2 C5 1.224(2) . ?
O3 C6 1.230(2) . ?
O4 C10 1.233(2) . ?
O5 C12 1.423(2) . ?
O5 H5O 0.89(3) . ?
O6 C14 1.424(2) . ?
O6 H6O 0.91(3) . ?
O7 C16 1.423(3) . ?
O7 H7O 0.84(3) . ?
O8 C18 1.418(2) . ?
O8 H8O 0.86(3) . ?
N1 C1 1.327(2) . ?
N1 C11 1.457(2) . ?
N1 H1N 0.86(2) . ?
N2 C5 1.328(2) . ?
N2 C13 1.458(2) . ?
N2 H2N 0.87(3) . ?
N3 C2 1.325(2) . ?
N3 C4 1.330(2) . ?
N4 C6 1.324(2) . ?
N4 C15 1.464(2) . ?
N4 H4N 0.89(3) . ?
N5 C10 1.326(2) . ?
N5 C17 1.463(2) . ?
N5 H5N 0.85(3) . ?
N8 C9 1.338(2) . ?
N8 C7 1.341(2) . ?
C1 C2 1.515(2) . ?
C2 C9 1.406(2) . ?
C4 C7 1.401(2) . ?
C4 C5 1.513(2) . ?
C6 C7 1.515(2) . ?
C9 C10 1.513(2) . ?
C11 C12 1.513(3) . ?
C11 H11A 1.00(3) . ?
C11 H11B 0.97(3) . ?
C12 H12A 1.01(3) . ?
C12 H12B 0.94(3) . ?
C13 C14 1.509(3) . ?
C13 H13A 0.98(3) . ?
C13 H13B 0.99(3) . ?
C14 H14A 0.99(3) . ?
C14 H14B 0.99(3) . ?
C15 C16 1.517(3) . ?
C15 H15A 1.05(3) . ?
C15 H15B 0.99(3) . ?
C16 H16A 1.01(3) . ?
C16 H16B 0.99(3) . ?
C17 C18 1.511(3) . ?
C17 H17A 1.02(2) . ?
C17 H17B 0.98(3) . ?
C18 H18A 0.97(2) . ?
C18 H18B 1.00(3) . ?
O1W H1W1 0.92(3) . ?
O1W H1W2 0.91(3) . ?

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 O5 H5O 111.5(17) . . ?
C14 O6 H6O 111.6(18) . . ?
C16 O7 H7O 113(2) . . ?
C18 O8 H8O 114(2) . . ?
C1 N1 C11 121.96(17) . . ?
C1 N1 H1N 118.9(15) . . ?
C11 N1 H1N 118.7(15) . . ?
C5 N2 C13 122.31(17) . . ?
C5 N2 H2N 116.4(16) . . ?
C13 N2 H2N 121.2(16) . . ?
C2 N3 C4 119.03(15) . . ?
C6 N4 C15 121.89(17) . . ?
C6 N4 H4N 119.2(18) . . ?
C15 N4 H4N 118.8(18) . . ?
C10 N5 C17 121.83(17) . . ?
C10 N5 H5N 119.6(18) . . ?
C17 N5 H5N 118.5(18) . . ?
C9 N8 C7 118.28(15) . . ?
O1 C1 N1 124.67(18) . . ?
O1 C1 C2 120.72(16) . . ?
N1 C1 C2 114.60(16) . . ?
N3 C2 C9 120.61(16) . . ?
N3 C2 C1 116.86(15) . . ?
C9 C2 C1 122.48(16) . . ?
N3 C4 C7 120.64(16) . . ?
N3 C4 C5 116.75(15) . . ?
C7 C4 C5 122.58(16) . . ?
O2 C5 N2 124.77(17) . . ?
O2 C5 C4 120.77(16) . . ?
N2 C5 C4 114.45(16) . . ?
O3 C6 N4 124.86(17) . . ?
O3 C6 C7 119.96(16) . . ?
N4 C6 C7 115.07(16) . . ?
N8 C7 C4 120.52(16) . . ?
N8 C7 C6 114.86(15) . . ?
C4 C7 C6 124.55(16) . . ?
N8 C9 C2 120.56(16) . . ?
N8 C9 C10 115.60(15) . . ?
C2 C9 C10 123.67(16) . . ?
O4 C10 N5 124.85(17) . . ?
O4 C10 C9 119.60(16) . . ?
N5 C10 C9 115.49(16) . . ?
N1 C11 C12 111.23(16) . . ?
N1 C11 H11A 110.5(16) . . ?
C12 C11 H11A 109.3(15) . . ?
N1 C11 H11B 111.1(16) . . ?
C12 C11 H11B 110.8(16) . . ?
H11A C11 H11B 104(2) . . ?
O5 C12 C11 110.83(17) . . ?
O5 C12 H12A 107.8(17) . . ?
C11 C12 H12A 107.7(18) . . ?
O5 C12 H12B 110.8(17) . . ?
C11 C12 H12B 107.4(17) . . ?
H12A C12 H12B 112(2) . . ?
N2 C13 C14 111.30(17) . . ?
N2 C13 H13A 109.1(15) . . ?
C14 C13 H13A 108.6(15) . . ?
N2 C13 H13B 109.0(16) . . ?
C14 C13 H13B 112.4(16) . . ?
H13A C13 H13B 106(2) . . ?
O6 C14 C13 109.97(18) . . ?
O6 C14 H14A 108.3(17) . . ?
C13 C14 H14A 108.0(18) . . ?
O6 C14 H14B 110.9(17) . . ?
C13 C14 H14B 109.1(17) . . ?
H14A C14 H14B 111(2) . . ?
N4 C15 C16 112.48(17) . . ?
N4 C15 H15A 105.4(13) . . ?
C16 C15 H15A 110.8(13) . . ?
N4 C15 H15B 109.7(16) . . ?
C16 C15 H15B 109.7(17) . . ?
H15A C15 H15B 109(2) . . ?
O7 C16 C15 108.59(17) . . ?
O7 C16 H16A 110.3(15) . . ?
C15 C16 H16A 110.7(15) . . ?
O7 C16 H16B 109.5(16) . . ?
C15 C16 H16B 105.6(17) . . ?
H16A C16 H16B 112(2) . . ?
N5 C17 C18 112.42(16) . . ?
N5 C17 H17A 103.1(13) . . ?
C18 C17 H17A 113.0(13) . . ?
N5 C17 H17B 109.1(15) . . ?
C18 C17 H17B 109.5(15) . . ?
H17A C17 H17B 110(2) . . ?
O8 C18 C17 109.40(16) . . ?
O8 C18 H18A 110.5(14) . . ?
C17 C18 H18A 111.3(13) . . ?
O8 C18 H18B 109.4(15) . . ?
C17 C18 H18B 108.3(16) . . ?
H18A C18 H18B 108(2) . . ?
H1W1 O1W H1W2 107(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
C11 N1 C1 O1 -2.8(3) . . . . ?
C11 N1 C1 C2 175.99(16) . . . . ?
C4 N3 C2 C9 2.9(2) . . . . ?
C4 N3 C2 C1 -174.64(15) . . . . ?
O1 C1 C2 N3 162.23(18) . . . . ?
N1 C1 C2 N3 -16.6(2) . . . . ?
O1 C1 C2 C9 -15.3(3) . . . . ?
N1 C1 C2 C9 165.90(17) . . . . ?
C2 N3 C4 C7 2.6(2) . . . . ?
C2 N3 C4 C5 -175.79(15) . . . . ?
C13 N2 C5 O2 -1.8(3) . . . . ?
C13 N2 C5 C4 178.67(16) . . . . ?
N3 C4 C5 O2 173.67(18) . . . . ?
C7 C4 C5 O2 -4.7(3) . . . . ?
N3 C4 C5 N2 -6.7(2) . . . . ?
C7 C4 C5 N2 174.93(17) . . . . ?
C15 N4 C6 O3 -1.3(3) . . . . ?
C15 N4 C6 C7 174.78(16) . . . . ?
C9 N8 C7 C4 2.9(3) . . . . ?
C9 N8 C7 C6 -174.18(16) . . . . ?
N3 C4 C7 N8 -5.6(3) . . . . ?
C5 C4 C7 N8 172.61(16) . . . . ?
N3 C4 C7 C6 171.10(16) . . . . ?
C5 C4 C7 C6 -10.6(3) . . . . ?
O3 C6 C7 N8 106.9(2) . . . . ?
N4 C6 C7 N8 -69.5(2) . . . . ?
O3 C6 C7 C4 -70.1(2) . . . . ?
N4 C6 C7 C4 113.6(2) . . . . ?
C7 N8 C9 C2 2.6(2) . . . . ?
C7 N8 C9 C10 -172.93(15) . . . . ?
N3 C2 C9 N8 -5.7(3) . . . . ?
C1 C2 C9 N8 171.75(16) . . . . ?
N3 C2 C9 C10 169.45(16) . . . . ?
C1 C2 C9 C10 -13.1(3) . . . . ?
C17 N5 C10 O4 -1.7(3) . . . . ?
C17 N5 C10 C9 175.25(15) . . . . ?
N8 C9 C10 O4 114.21(19) . . . . ?
C2 C9 C10 O4 -61.1(2) . . . . ?
N8 C9 C10 N5 -62.9(2) . . . . ?
C2 C9 C10 N5 121.78(19) . . . . ?
C1 N1 C11 C12 -90.5(2) . . . . ?
N1 C11 C12 O5 -175.22(16) . . . . ?
C5 N2 C13 C14 -95.9(2) . . . . ?
N2 C13 C14 O6 -173.68(17) . . . . ?
C6 N4 C15 C16 -71.9(2) . . . . ?
N4 C15 C16 O7 -59.1(2) . . . . ?
C10 N5 C17 C18 -73.8(2) . . . . ?
N5 C17 C18 O8 -59.8(2) . . . . ?

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
O5 H5O O1 0.89(3) 1.87(3) 2.712(2) 157(2) 3_667
O6 H6O O2 0.91(3) 1.84(3) 2.716(2) 161(3) 3_565
O7 H7O O6 0.84(3) 1.89(3) 2.708(2) 163(3) 2_545
O8 H8O O5 0.86(3) 1.87(3) 2.697(2) 161(3) 2_646
N1 H1N O1W 0.86(2) 2.10(2) 2.889(2) 152(2) 3_666
N2 H2N N3 0.87(3) 2.23(2) 2.665(2) 110.8(19) .
N2 H2N O1W 0.87(3) 2.10(3) 2.878(2) 150(2) 3_666
N4 H4N O8 0.89(3) 1.92(3) 2.809(2) 177(3) 4_565
N5 H5N O7 0.85(3) 1.96(3) 2.804(2) 174(3) 4_566
O1W H1W1 O3 0.92(3) 1.82(3) 2.728(2) 170(3) 1_655
O1W H1W2 O4 0.91(3) 1.82(3) 2.732(2) 178(3) .

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_v24d
_database_code_depnum_ccdc_archive 'CCDC 2092504'
loop_
_audit_author_name
_audit_author_address
'Victor W. Day'
;University of Kansas
United States of America
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H56 N6 O4'
_chemical_formula_weight         588.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   44.553(4)
_cell_length_b                   4.9317(4)
_cell_length_c                   15.7652(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.399(6)
_cell_angle_gamma                90
_cell_volume                     3463.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5104
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      67.29

_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11408
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.983
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_full        66.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3042
_reflns_number_gt                2464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+38.1385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.1242
_refine_ls_wR_factor_ref         0.3011
_refine_ls_wR_factor_gt          0.2927
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27414(9) 0.7922(7) 0.1448(2) 0.0377(9) Uani 1 1 d . . . . .
O2 O 0.17468(9) 0.0262(7) -0.0303(3) 0.0392(10) Uani 1 1 d . . . . .
N1 N 0.28352(10) 0.3773(9) 0.2021(3) 0.0316(10) Uani 1 1 d . . . . .
H1A H 0.2826 0.2017 0.1925 0.038 Uiso 1 1 calc R U . . .
N2 N 0.17183(10) 0.4751(9) -0.0153(3) 0.0360(11) Uani 1 1 d . . . . .
H2A H 0.1816 0.6253 -0.0029 0.043 Uiso 1 1 calc R U . . .
N3 N 0.23192(9) 0.4029(8) 0.0547(2) 0.0258(9) Uani 1 1 d . . . . .
C1 C 0.27408(11) 0.5408(10) 0.1410(3) 0.0277(11) Uani 1 1 d . . . . .
C2 C 0.26142(11) 0.3950(9) 0.0642(3) 0.0236(10) Uani 1 1 d . . . . .
C4 C 0.22005(11) 0.2589(9) -0.0095(3) 0.0259(10) Uani 1 1 d . . . . .
C5 C 0.18694(12) 0.2467(10) -0.0184(3) 0.0290(11) Uani 1 1 d . . . . .
C6 C 0.29554(13) 0.4659(12) 0.2852(3) 0.0360(12) Uani 1 1 d . . . . .
H6A H 0.2830 0.3893 0.3309 0.043 Uiso 1 1 calc R U . . .
H6B H 0.2944 0.6660 0.2889 0.043 Uiso 1 1 calc R U . . .
C7 C 0.32761(14) 0.3781(13) 0.2988(4) 0.0442(14) Uani 1 1 d . . . . .
H7A H 0.3288 0.1794 0.2906 0.053 Uiso 1 1 calc R U . . .
H7B H 0.3333 0.4166 0.3584 0.053 Uiso 1 1 calc R U . . .
C8 C 0.35029(13) 0.5122(13) 0.2412(4) 0.0431(14) Uani 1 1 d . . . . .
H8A H 0.3436 0.4893 0.1817 0.052 Uiso 1 1 calc R U . . .
H8B H 0.3507 0.7090 0.2536 0.052 Uiso 1 1 calc R U . . .
C9 C 0.38165(14) 0.4020(15) 0.2502(4) 0.0499(16) Uani 1 1 d . . . . .
H9A H 0.3811 0.2040 0.2399 0.060 Uiso 1 1 calc R U . . .
H9B H 0.3886 0.4305 0.3093 0.060 Uiso 1 1 calc R U . . .
C10 C 0.40422(16) 0.5272(17) 0.1912(5) 0.065(2) Uani 1 1 d . . . . .
H10A H 0.4052 0.7243 0.2027 0.078 Uiso 1 1 calc R U . . .
H10B H 0.3970 0.5038 0.1321 0.078 Uiso 1 1 calc R U . . .
C11 C 0.43565(16) 0.410(2) 0.1983(6) 0.083(3) Uani 1 1 d . . . . .
H11A H 0.4489 0.5020 0.1581 0.124 Uiso 1 1 calc R U . . .
H11B H 0.4433 0.4366 0.2561 0.124 Uiso 1 1 calc R U . . .
H11C H 0.4351 0.2157 0.1854 0.124 Uiso 1 1 calc R U . . .
C12 C 0.13986(12) 0.4908(12) -0.0313(4) 0.0408(13) Uani 1 1 d . . . . .
H12A H 0.1350 0.3740 -0.0805 0.049 Uiso 1 1 calc R U . . .
H12B H 0.1348 0.6796 -0.0471 0.049 Uiso 1 1 calc R U . . .
C13 C 0.12036(14) 0.4085(17) 0.0412(4) 0.0555(18) Uani 1 1 d . . . . .
H13A H 0.1267 0.5081 0.0929 0.067 Uiso 1 1 calc R U . . .
H13B H 0.1230 0.2122 0.0522 0.067 Uiso 1 1 calc R U . . .
C14 C 0.08734(14) 0.4667(17) 0.0228(5) 0.0579(18) Uani 1 1 d . . . . .
H14A H 0.0848 0.6648 0.0154 0.069 Uiso 1 1 calc R U . . .
H14B H 0.0818 0.3793 -0.0316 0.069 Uiso 1 1 calc R U . . .
C15 C 0.06582(16) 0.373(3) 0.0894(6) 0.087(3) Uani 1 1 d . . . . .
H15A H 0.0712 0.4602 0.1440 0.105 Uiso 1 1 calc R U . . .
H15B H 0.0681 0.1746 0.0968 0.105 Uiso 1 1 calc R U . . .
C16 C 0.03328(17) 0.435(3) 0.0692(7) 0.109(4) Uani 1 1 d . . . . .
H16A H 0.0313 0.6306 0.0570 0.131 Uiso 1 1 calc R U . . .
H16B H 0.0274 0.3344 0.0173 0.131 Uiso 1 1 calc R U . . .
C17 C 0.0121(2) 0.362(5) 0.1387(9) 0.192(10) Uani 1 1 d . . . . .
H17A H -0.0085 0.4071 0.1213 0.289 Uiso 1 1 calc R U . . .
H17B H 0.0135 0.1669 0.1503 0.289 Uiso 1 1 calc R U . . .
H17C H 0.0174 0.4635 0.1901 0.289 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
O1 C1 1.241(6) . ?
O2 C5 1.231(6) . ?
N1 C1 1.323(7) . ?
N1 C6 1.478(6) . ?
N1 H1A 0.8800 . ?
N2 C5 1.314(7) . ?
N2 C12 1.447(7) . ?
N2 H2A 0.8800 . ?
N3 C2 1.322(6) . ?
N3 C4 1.343(6) . ?
C1 C2 1.514(7) . ?
C2 C4 1.418(6) 7 ?
C4 C2 1.418(6) 7 ?
C4 C5 1.482(7) . ?
C6 C7 1.507(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.515(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.505(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.507(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.496(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.500(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.495(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 125.2(4) . . ?
C1 N1 H1A 117.4 . . ?
C6 N1 H1A 117.4 . . ?
C5 N2 C12 122.9(5) . . ?
C5 N2 H2A 118.5 . . ?
C12 N2 H2A 118.5 . . ?
C2 N3 C4 117.1(4) . . ?
O1 C1 N1 125.0(5) . . ?
O1 C1 C2 120.9(5) . . ?
N1 C1 C2 114.1(4) . . ?
N3 C2 C4 122.0(4) . 7 ?
N3 C2 C1 116.2(4) . . ?
C4 C2 C1 121.7(4) 7 . ?
N3 C4 C2 120.9(5) . 7 ?
N3 C4 C5 118.6(4) . . ?
C2 C4 C5 120.2(4) 7 . ?
O2 C5 N2 122.4(5) . . ?
O2 C5 C4 119.4(4) . . ?
N2 C5 C4 118.1(4) . . ?
N1 C6 C7 112.2(4) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 115.2(5) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 114.1(5) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 114.7(6) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 114.6(7) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 115.4(5) . . ?
N2 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
N2 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 111.6(6) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 115.5(6) . . ?
C15 C14 H14A 108.4 . . ?
C13 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C13 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 114.0(8) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 114.0(9) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 N1 C1 O1 0.4(9) . . . . ?
C6 N1 C1 C2 -177.0(4) . . . . ?
C4 N3 C2 C4 -0.3(7) . . . 7 ?
C4 N3 C2 C1 -175.4(4) . . . . ?
O1 C1 C2 N3 -71.2(6) . . . . ?
N1 C1 C2 N3 106.4(5) . . . . ?
O1 C1 C2 C4 113.7(6) . . . 7 ?
N1 C1 C2 C4 -68.8(6) . . . 7 ?
C2 N3 C4 C2 0.3(7) . . . 7 ?
C2 N3 C4 C5 175.6(4) . . . . ?
C12 N2 C5 O2 -4.4(8) . . . . ?
C12 N2 C5 C4 173.9(5) . . . . ?
N3 C4 C5 O2 -132.7(5) . . . . ?
C2 C4 C5 O2 42.7(6) 7 . . . ?
N3 C4 C5 N2 48.9(6) . . . . ?
C2 C4 C5 N2 -135.7(5) 7 . . . ?
C1 N1 C6 C7 -118.2(6) . . . . ?
N1 C6 C7 C8 67.2(7) . . . . ?
C6 C7 C8 C9 -174.4(5) . . . . ?
C7 C8 C9 C10 178.1(6) . . . . ?
C8 C9 C10 C11 -178.2(6) . . . . ?
C5 N2 C12 C13 79.6(7) . . . . ?
N2 C12 C13 C14 172.4(6) . . . . ?
C12 C13 C14 C15 175.8(8) . . . . ?
C13 C14 C15 C16 179.9(9) . . . . ?
C14 C15 C16 C17 -175.2(13) . . . . ?

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
N1 H1A O1 0.88 2.19 3.052(5) 167.4 1_545
N2 H2A O2 0.88 2.05 2.731(6) 133.9 1_565
C6 H6A O1 0.99 2.62 3.411(7) 137.0 4_545
C12 H12B O2 0.99 2.48 3.063(7) 117.4 1_565

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_k22k
_database_code_depnum_ccdc_archive 'CCDC 1453984'
loop_
_audit_author_name
_audit_author_address
'Victor Day'
;University of Kansas
United States of America
;
_audit_update_record             
;
2019-12-28 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 N6 O12'
_chemical_formula_weight         604.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0587(19)
_cell_length_b                   14.955(3)
_cell_length_c                   8.8548(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.133(2)
_cell_angle_gamma                90
_cell_volume                     1436.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    228(2)
_cell_measurement_reflns_used    2384
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.14

_exptl_crystal_description       Irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      228(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11256
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         30.521
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4319
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.2014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4319
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20215(12) 0.10839(8) 0.28074(16) 0.0436(3) Uani 1 1 d . . . . .
O2 O 0.06081(13) -0.16941(9) 0.79152(14) 0.0441(3) Uani 1 1 d . . . . .
O3 O 0.36826(13) -0.12899(8) 0.14181(15) 0.0443(3) Uani 1 1 d . . . . .
O4 O 0.39685(16) -0.31796(10) 0.0563(2) 0.0606(5) Uani 1 1 d . . . . .
H40 H 0.445(2) -0.2975(17) 0.133(3) 0.076(9) Uiso 1 1 d . . . . .
O5 O -0.17496(11) -0.32839(8) 0.75172(14) 0.0389(3) Uani 1 1 d . . . . .
O6 O -0.38712(14) -0.21394(10) 0.7936(2) 0.0568(4) Uani 1 1 d . . . . .
H6O H -0.325(2) -0.1867(17) 0.767(3) 0.079(8) Uiso 1 1 d . . . . .
N1 N 0.29493(13) -0.01855(9) 0.38251(18) 0.0330(3) Uani 1 1 d . . . . .
H1N H 0.2877(19) -0.0675(14) 0.440(2) 0.053(6) Uiso 1 1 d . . . . .
N2 N -0.01775(14) -0.24038(9) 0.56781(18) 0.0326(3) Uani 1 1 d . . . . .
H2N H -0.0483(18) -0.2314(13) 0.472(2) 0.044(6) Uiso 1 1 d . . . . .
N3 N 0.09552(12) -0.06015(8) 0.50169(15) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.20280(15) 0.04000(10) 0.35753(19) 0.0284(3) Uani 1 1 d . . . . .
C2 C 0.09480(14) 0.01939(10) 0.43205(18) 0.0263(3) Uani 1 1 d . . . . .
C4 C 0.00101(14) -0.08024(10) 0.56969(18) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.01460(15) -0.16874(10) 0.65461(19) 0.0283(4) Uani 1 1 d . . . . .
C6 C 0.40474(16) -0.00770(12) 0.3167(2) 0.0342(4) Uani 1 1 d . . . . .
H6A H 0.4289(17) 0.0567(13) 0.324(2) 0.040(5) Uiso 1 1 d . . . . .
H6B H 0.4703(17) -0.0441(12) 0.378(2) 0.034(5) Uiso 1 1 d . . . . .
C7 C 0.38775(19) -0.03622(12) 0.1517(2) 0.0382(4) Uani 1 1 d . . . . .
H7A H 0.3191(19) -0.0046(14) 0.084(2) 0.052(6) Uiso 1 1 d . . . . .
H7B H 0.4655(19) -0.0212(13) 0.111(2) 0.050(6) Uiso 1 1 d . . . . .
C8 C 0.3504(2) -0.16151(14) -0.0120(3) 0.0504(5) Uani 1 1 d . . . . .
H8A H 0.285(2) -0.1237(15) -0.079(3) 0.063(7) Uiso 1 1 d . . . . .
H8B H 0.430(2) -0.1571(16) -0.053(3) 0.075(8) Uiso 1 1 d . . . . .
C9 C 0.3084(2) -0.25608(15) -0.0155(3) 0.0582(6) Uani 1 1 d . . . . .
H9A H 0.284(2) -0.2774(15) -0.126(3) 0.068(7) Uiso 1 1 d . . . . .
H9B H 0.243(3) -0.2578(17) 0.038(3) 0.078(9) Uiso 1 1 d . . . . .
C10 C -0.0021(2) -0.33121(11) 0.6277(2) 0.0395(4) Uani 1 1 d . . . . .
H10A H 0.0504(17) -0.3285(12) 0.730(2) 0.039(5) Uiso 1 1 d . . . . .
H10B H 0.0402(19) -0.3660(13) 0.559(2) 0.049(6) Uiso 1 1 d . . . . .
C11 C -0.1228(2) -0.37429(12) 0.6389(2) 0.0405(5) Uani 1 1 d . . . . .
H11A H -0.1839(19) -0.3707(13) 0.540(2) 0.050(6) Uiso 1 1 d . . . . .
H11B H -0.1092(17) -0.4362(14) 0.666(2) 0.046(5) Uiso 1 1 d . . . . .
C12 C -0.29613(19) -0.35819(14) 0.7595(3) 0.0460(5) Uani 1 1 d . . . . .
H12A H -0.2922(18) -0.4216(14) 0.799(2) 0.051(6) Uiso 1 1 d . . . . .
H12B H -0.347(2) -0.3553(14) 0.654(3) 0.056(6) Uiso 1 1 d . . . . .
C13 C -0.3498(2) -0.29727(14) 0.8628(3) 0.0470(5) Uani 1 1 d . . . . .
H13A H -0.2828(19) -0.2891(13) 0.960(2) 0.048(6) Uiso 1 1 d . . . . .
H13B H -0.424(2) -0.3245(15) 0.885(3) 0.068(7) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2275(19) . ?
O2 C5 1.2214(19) . ?
O3 C7 1.404(2) . ?
O3 C8 1.423(2) . ?
O4 C9 1.406(3) . ?
O4 H40 0.84(3) . ?
O5 C11 1.423(2) . ?
O5 C12 1.426(2) . ?
O6 C13 1.415(2) . ?
O6 H6O 0.87(3) . ?
N1 C1 1.329(2) . ?
N1 C6 1.454(2) . ?
N1 H1N 0.90(2) . ?
N2 C5 1.327(2) . ?
N2 C10 1.456(2) . ?
N2 H2N 0.86(2) . ?
N3 C4 1.337(2) . ?
N3 C2 1.3391(19) . ?
C1 C2 1.504(2) . ?
C2 C4 1.395(2) 3_556 ?
C4 C2 1.395(2) 3_556 ?
C4 C5 1.515(2) . ?
C6 C7 1.499(3) . ?
C6 H6A 0.999(19) . ?
C6 H6B 0.983(18) . ?
C7 H7A 0.99(2) . ?
C7 H7B 1.02(2) . ?
C8 C9 1.487(3) . ?
C8 H8A 1.01(2) . ?
C8 H8B 1.01(3) . ?
C9 H9A 1.01(2) . ?
C9 H9B 0.94(3) . ?
C10 C11 1.503(3) . ?
C10 H10A 0.976(19) . ?
C10 H10B 0.99(2) . ?
C11 H11A 1.00(2) . ?
C11 H11B 0.96(2) . ?
C12 C13 1.493(3) . ?
C12 H12A 1.01(2) . ?
C12 H12B 0.99(2) . ?
C13 H13A 1.03(2) . ?
C13 H13B 0.97(2) . ?

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
C7 O3 C8 112.87(15) . . ?
C9 O4 H40 113.8(18) . . ?
C11 O5 C12 113.27(15) . . ?
C13 O6 H6O 110.4(17) . . ?
C1 N1 C6 122.19(15) . . ?
C1 N1 H1N 118.6(13) . . ?
C6 N1 H1N 119.1(13) . . ?
C5 N2 C10 122.84(16) . . ?
C5 N2 H2N 117.1(13) . . ?
C10 N2 H2N 120.0(13) . . ?
C4 N3 C2 118.12(13) . . ?
O1 C1 N1 124.29(15) . . ?
O1 C1 C2 119.58(14) . . ?
N1 C1 C2 116.12(14) . . ?
N3 C2 C4 121.45(14) . 3_556 ?
N3 C2 C1 116.71(13) . . ?
C4 C2 C1 121.83(13) 3_556 . ?
N3 C4 C2 120.44(14) . 3_556 ?
N3 C4 C5 114.11(13) . . ?
C2 C4 C5 125.30(14) 3_556 . ?
O2 C5 N2 125.64(15) . . ?
O2 C5 C4 118.82(15) . . ?
N2 C5 C4 115.34(14) . . ?
N1 C6 C7 113.69(16) . . ?
N1 C6 H6A 108.3(11) . . ?
C7 C6 H6A 108.8(10) . . ?
N1 C6 H6B 107.4(10) . . ?
C7 C6 H6B 108.9(10) . . ?
H6A C6 H6B 109.7(15) . . ?
O3 C7 C6 109.32(15) . . ?
O3 C7 H7A 110.1(12) . . ?
C6 C7 H7A 113.0(11) . . ?
O3 C7 H7B 109.0(11) . . ?
C6 C7 H7B 108.9(11) . . ?
H7A C7 H7B 106.4(16) . . ?
O3 C8 C9 109.3(2) . . ?
O3 C8 H8A 108.6(13) . . ?
C9 C8 H8A 109.5(13) . . ?
O3 C8 H8B 110.5(14) . . ?
C9 C8 H8B 110.0(14) . . ?
H8A C8 H8B 108.9(19) . . ?
O4 C9 C8 115.5(2) . . ?
O4 C9 H9A 105.3(13) . . ?
C8 C9 H9A 110.1(13) . . ?
O4 C9 H9B 106.9(16) . . ?
C8 C9 H9B 106.5(16) . . ?
H9A C9 H9B 113(2) . . ?
N2 C10 C11 112.26(16) . . ?
N2 C10 H10A 107.8(11) . . ?
C11 C10 H10A 109.5(11) . . ?
N2 C10 H10B 107.7(12) . . ?
C11 C10 H10B 110.4(12) . . ?
H10A C10 H10B 109.1(17) . . ?
O5 C11 C10 108.98(15) . . ?
O5 C11 H11A 106.9(12) . . ?
C10 C11 H11A 112.3(12) . . ?
O5 C11 H11B 110.8(11) . . ?
C10 C11 H11B 109.3(11) . . ?
H11A C11 H11B 108.5(16) . . ?
O5 C12 C13 109.10(17) . . ?
O5 C12 H12A 109.4(12) . . ?
C13 C12 H12A 111.1(12) . . ?
O5 C12 H12B 107.8(12) . . ?
C13 C12 H12B 109.3(12) . . ?
H12A C12 H12B 110.1(17) . . ?
O6 C13 C12 112.90(18) . . ?
O6 C13 H13A 111.1(11) . . ?
C12 C13 H13A 106.0(11) . . ?
O6 C13 H13B 105.6(13) . . ?
C12 C13 H13B 108.8(14) . . ?
H13A C13 H13B 112.5(18) . . ?

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
C6 N1 C1 O1 -1.5(3) . . . . ?
C6 N1 C1 C2 179.45(15) . . . . ?
C4 N3 C2 C4 0.3(2) . . . 3_556 ?
C4 N3 C2 C1 179.68(14) . . . . ?
O1 C1 C2 N3 173.75(15) . . . . ?
N1 C1 C2 N3 -7.1(2) . . . . ?
O1 C1 C2 C4 -6.8(2) . . . 3_556 ?
N1 C1 C2 C4 172.27(15) . . . 3_556 ?
C2 N3 C4 C2 -0.3(2) . . . 3_556 ?
C2 N3 C4 C5 -175.95(14) . . . . ?
C10 N2 C5 O2 0.4(3) . . . . ?
C10 N2 C5 C4 175.23(15) . . . . ?
N3 C4 C5 O2 92.74(18) . . . . ?
C2 C4 C5 O2 -82.7(2) 3_556 . . . ?
N3 C4 C5 N2 -82.51(18) . . . . ?
C2 C4 C5 N2 102.05(19) 3_556 . . . ?
C1 N1 C6 C7 -79.8(2) . . . . ?
C8 O3 C7 C6 179.59(16) . . . . ?
N1 C6 C7 O3 -66.2(2) . . . . ?
C7 O3 C8 C9 -169.93(18) . . . . ?
O3 C8 C9 O4 -69.0(3) . . . . ?
C5 N2 C10 C11 108.4(2) . . . . ?
C12 O5 C11 C10 173.70(16) . . . . ?
N2 C10 C11 O5 -66.2(2) . . . . ?
C11 O5 C12 C13 -171.45(16) . . . . ?
O5 C12 C13 O6 75.0(2) . . . . ?

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
O4 H40 O6 0.84(3) 2.12(3) 2.900(2) 156(2) 4_655
O6 H6O O1 0.87(3) 1.90(3) 2.7622(19) 170(2) 3_556
N1 H1N O4 0.90(2) 2.23(2) 2.991(2) 141.6(18) 4_556
N2 H2N O2 0.86(2) 2.64(2) 3.063(2) 111.8(15) 4
N2 H2N O5 0.86(2) 2.35(2) 3.168(2) 159.3(18) 4
C6 H6A O6 0.999(19) 2.578(19) 3.451(2) 145.9(14) 3_556
C8 H8A O2 1.01(2) 2.61(2) 3.338(3) 128.4(16) 1_554
C10 H10B O2 0.99(2) 2.48(2) 3.185(2) 128.3(15) 4

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

