# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1574972'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N3 O4'
_chemical_formula_sum            'C11 H15 N3 O4'
_chemical_formula_weight         253.26

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2124(6)
_cell_length_b                   10.5820(5)
_cell_length_c                   17.2167(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1314.01(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2790
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      28.12

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.279
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            5999
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2566
_reflns_number_gt                2161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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-2013 (Sheldrick, 2013)'
_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)+(0.0512P)²+0.0475P] 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_abs_structure_details 
;
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.0834(3) 0.2191(2) 0.53831(13) 0.0539(5) Uani 1 1 d . . . . .
H1 H 0.1482 0.2651 0.4970 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2195(3) 0.14169(18) 0.58638(12) 0.0476(5) Uani 1 1 d . . . . .
H2 H 0.3405 0.1309 0.5613 0.057 Uiso 1 1 calc R U . . .
C3 C 0.2294(3) 0.21366(18) 0.66248(11) 0.0467(5) Uani 1 1 d . . . . .
H3 H 0.3225 0.2808 0.6589 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0373(3) 0.27074(19) 0.66779(13) 0.0511(5) Uani 1 1 d . . . . .
H4 H -0.0500 0.2058 0.6855 0.061 Uiso 1 1 calc R U . . .
C5 C 0.0183(4) 0.3860(2) 0.71890(15) 0.0675(7) Uani 1 1 d . . . . .
H5A H -0.1081 0.4170 0.7160 0.081 Uiso 1 1 calc R U . . .
H5B H 0.0426 0.3623 0.7724 0.081 Uiso 1 1 calc R U . . .
C6 C -0.0051(4) 0.0089(2) 0.53533(13) 0.0550(6) Uani 1 1 d . . . . .
C7 C -0.1799(5) -0.0479(3) 0.56659(18) 0.0888(10) Uani 1 1 d . . . . .
H7A H -0.1554 -0.1322 0.5845 0.133 Uiso 1 1 calc R U . . .
H7B H -0.2719 -0.0505 0.5263 0.133 Uiso 1 1 calc R U . . .
H7C H -0.2246 0.0024 0.6090 0.133 Uiso 1 1 calc R U . . .
C8 C 0.0816(6) -0.0676(3) 0.47137(18) 0.1042(13) Uani 1 1 d . . . . .
H8A H 0.1874 -0.0233 0.4512 0.156 Uiso 1 1 calc R U . . .
H8B H -0.0072 -0.0801 0.4306 0.156 Uiso 1 1 calc R U . . .
H8C H 0.1200 -0.1480 0.4915 0.156 Uiso 1 1 calc R U . . .
C9 C 0.4546(4) 0.1186(2) 0.74476(15) 0.0638(7) Uani 1 1 d . . . . .
H9A H 0.5199 0.1039 0.6963 0.077 Uiso 1 1 calc R U . . .
H9B H 0.4683 0.0436 0.7767 0.077 Uiso 1 1 calc R U . . .
C10 C 0.5393(3) 0.2260(2) 0.78479(13) 0.0551(6) Uani 1 1 d . . . . .
C11 C 0.6107(4) 0.3084(2) 0.81861(17) 0.0692(7) Uani 1 1 d . . . . .
H11 H 0.6675 0.3739 0.8456 0.083 Uiso 1 1 calc R U . . .
N1 N 0.1469(4) 0.48814(18) 0.69605(14) 0.0708(6) Uani 1 1 d . . . . .
N2 N 0.0822(3) 0.56266(19) 0.64963(14) 0.0663(6) Uani 1 1 d . . . . .
N3 N 0.0389(5) 0.6386(3) 0.60786(18) 0.0995(9) Uani 1 1 d . . . . .
O1 O -0.0411(3) 0.13275(15) 0.50707(10) 0.0720(6) Uani 1 1 d . . . . .
O2 O 0.1226(2) 0.02583(12) 0.59783(8) 0.0514(4) Uani 1 1 d . . . . .
O3 O 0.2640(2) 0.13786(14) 0.72871(9) 0.0586(5) Uani 1 1 d . . . . .
O4 O -0.0056(2) 0.30390(14) 0.58952(9) 0.0603(4) Uani 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
C1 O1 1.390(3) . ?
C1 O4 1.412(3) . ?
C1 C2 1.523(3) . ?
C1 H1 0.9800 . ?
C2 O2 1.425(3) . ?
C2 C3 1.517(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.416(2) . ?
C3 C4 1.514(3) . ?
C3 H3 0.9800 . ?
C4 O4 1.426(3) . ?
C4 C5 1.510(3) . ?
C4 H4 0.9800 . ?
C5 N1 1.478(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.422(3) . ?
C6 O2 1.427(3) . ?
C6 C7 1.497(4) . ?
C6 C8 1.502(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.417(3) . ?
C9 C10 1.463(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.168(3) . ?
C11 H11 0.9300 . ?
N1 N2 1.216(3) . ?
N2 N3 1.123(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
O1 C1 O4 111.5(2) . . ?
O1 C1 C2 105.83(17) . . ?
O4 C1 C2 107.18(17) . . ?
O1 C1 H1 110.7 . . ?
O4 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
O2 C2 C3 109.61(16) . . ?
O2 C2 C1 102.81(17) . . ?
C3 C2 C1 103.26(17) . . ?
O2 C2 H2 113.4 . . ?
C3 C2 H2 113.4 . . ?
C1 C2 H2 113.4 . . ?
O3 C3 C4 109.77(18) . . ?
O3 C3 C2 114.79(16) . . ?
C4 C3 C2 102.09(17) . . ?
O3 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
O4 C4 C5 109.40(18) . . ?
O4 C4 C3 103.86(18) . . ?
C5 C4 C3 116.1(2) . . ?
O4 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
N1 C5 C4 112.3(2) . . ?
N1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 O2 105.06(16) . . ?
O1 C6 C7 109.8(2) . . ?
O2 C6 C7 108.83(19) . . ?
O1 C6 C8 108.7(2) . . ?
O2 C6 C8 110.6(2) . . ?
C7 C6 C8 113.4(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C10 112.7(2) . . ?
O3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 177.3(2) . . ?
C10 C11 H11 180.0 . . ?
N2 N1 C5 114.1(2) . . ?
N3 N2 N1 172.8(3) . . ?
C1 O1 C6 110.85(17) . . ?
C2 O2 C6 108.69(15) . . ?
C3 O3 C9 114.15(19) . . ?
C1 O4 C4 109.58(15) . . ?

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 C1 C2 O2 -18.4(2) . . . . ?
O4 C1 C2 O2 100.61(19) . . . . ?
O1 C1 C2 C3 -132.47(19) . . . . ?
O4 C1 C2 C3 -13.4(2) . . . . ?
O2 C2 C3 O3 40.2(2) . . . . ?
C1 C2 C3 O3 149.24(19) . . . . ?
O2 C2 C3 C4 -78.45(19) . . . . ?
C1 C2 C3 C4 30.6(2) . . . . ?
O3 C3 C4 O4 -159.73(16) . . . . ?
C2 C3 C4 O4 -37.55(19) . . . . ?
O3 C3 C4 C5 80.1(2) . . . . ?
C2 C3 C4 C5 -157.69(18) . . . . ?
O4 C4 C5 N1 -61.2(3) . . . . ?
C3 C4 C5 N1 55.9(3) . . . . ?
C4 C5 N1 N2 91.4(3) . . . . ?
O4 C1 O1 C6 -111.9(2) . . . . ?
C2 C1 O1 C6 4.3(3) . . . . ?
O2 C6 O1 C1 11.7(3) . . . . ?
C7 C6 O1 C1 128.6(2) . . . . ?
C8 C6 O1 C1 -106.7(3) . . . . ?
C3 C2 O2 C6 135.54(19) . . . . ?
C1 C2 O2 C6 26.2(2) . . . . ?
O1 C6 O2 C2 -24.3(2) . . . . ?
C7 C6 O2 C2 -141.9(2) . . . . ?
C8 C6 O2 C2 92.9(2) . . . . ?
C4 C3 O3 C9 -157.80(18) . . . . ?
C2 C3 O3 C9 87.9(2) . . . . ?
C10 C9 O3 C3 80.1(3) . . . . ?
O1 C1 O4 C4 104.6(2) . . . . ?
C2 C1 O4 C4 -10.7(2) . . . . ?
C5 C4 O4 C1 155.2(2) . . . . ?
C3 C4 O4 C1 30.6(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
C1 H1 O1 0.98 2.49 3.225(3) 131.7 3_556

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030

_shelxl_version_number           2014-3

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

data_COMPOUND_2
_database_code_depnum_ccdc_archive 'CCDC 1574973'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N3 O4'
_chemical_formula_sum            'C11 H15 N3 O4'
_chemical_formula_weight         253.26

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.9281(2)
_cell_length_b                   9.8404(3)
_cell_length_c                   11.7942(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.5350(10)
_cell_angle_gamma                90
_cell_volume                     1257.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4418
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      24.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.338
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            9548
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.852
_reflns_number_total             3885
_reflns_number_gt                3283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_max     0.739
_reflns_Friedel_fraction_full    0.719

_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-2013 (Sheldrick, 2013)'
_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)+(0.0410P)²] 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_abs_structure_details 
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     329
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
C1A C 0.3378(3) -0.1229(4) 1.3569(3) 0.0704(9) Uani 1 1 d . . . . .
H1A H 0.2621 -0.1243 1.3932 0.084 Uiso 1 1 calc R U . . .
C2A C 0.3084(2) -0.0915(3) 1.2303(3) 0.0612(7) Uani 1 1 d . . . . .
H2A H 0.2208 -0.1029 1.2013 0.073 Uiso 1 1 calc R U . . .
C1B C 0.1762(2) 0.4827(3) 0.8330(2) 0.0575(7) Uani 1 1 d . . . . .
H1B H 0.1969 0.5701 0.8704 0.069 Uiso 1 1 calc R U . . .
C3A C 0.3520(2) 0.0519(3) 1.2221(2) 0.0522(7) Uani 1 1 d . . . . .
H3A H 0.2889 0.1136 1.2445 0.063 Uiso 1 1 calc R U . . .
C2B C 0.0429(2) 0.4816(3) 0.7768(2) 0.0555(7) Uani 1 1 d . . . . .
H2B H -0.0085 0.5500 0.8081 0.067 Uiso 1 1 calc R U . . .
C4A C 0.4631(2) 0.0533(3) 1.3143(2) 0.0494(6) Uani 1 1 d . . . . .
H4A H 0.5317 0.0037 1.2878 0.059 Uiso 1 1 calc R U . . .
C3B C 0.0557(2) 0.5045(3) 0.6527(2) 0.0520(6) Uani 1 1 d . . . . .
H3B H 0.0719 0.6011 0.6409 0.062 Uiso 1 1 calc R U . . .
C5A C 0.5055(2) 0.1929(3) 1.3558(2) 0.0588(8) Uani 1 1 d . . . . .
H5A1 H 0.4351 0.2473 1.3701 0.071 Uiso 1 1 calc R U . . .
H5A2 H 0.5612 0.1854 1.4267 0.071 Uiso 1 1 calc R U . . .
C4B C 0.17252(18) 0.4234(3) 0.6414(2) 0.0470(6) Uani 1 1 d . . . . .
H4B H 0.1546 0.3258 0.6409 0.056 Uiso 1 1 calc R U . . .
C6A C 0.4085(3) -0.2976(4) 1.2527(3) 0.0702(8) Uani 1 1 d . . . . .
C5B C 0.2345(2) 0.4604(3) 0.5395(2) 0.0572(7) Uani 1 1 d . . . . .
H5B1 H 0.2429 0.5583 0.5349 0.069 Uiso 1 1 calc R U . . .
H5B2 H 0.3163 0.4204 0.5464 0.069 Uiso 1 1 calc R U . . .
C7A C 0.5377(3) -0.3443(5) 1.2496(4) 0.1074(14) Uani 1 1 d . . . . .
H7A1 H 0.5924 -0.2675 1.2579 0.161 Uiso 1 1 calc R U . . .
H7A2 H 0.5435 -0.3884 1.1778 0.161 Uiso 1 1 calc R U . . .
H7A3 H 0.5606 -0.4072 1.3110 0.161 Uiso 1 1 calc R U . . .
C6B C 0.0777(2) 0.2928(3) 0.8935(2) 0.0540(7) Uani 1 1 d . . . . .
C8A C 0.3133(4) -0.4064(5) 1.2170(4) 0.1205(17) Uani 1 1 d . . . . .
H8A1 H 0.3259 -0.4818 1.2689 0.181 Uiso 1 1 calc R U . . .
H8A2 H 0.3216 -0.4365 1.1410 0.181 Uiso 1 1 calc R U . . .
H8A3 H 0.2321 -0.3699 1.2185 0.181 Uiso 1 1 calc R U . . .
C7B C 0.1167(3) 0.1521(4) 0.8671(3) 0.0863(10) Uani 1 1 d . . . . .
H7B1 H 0.1638 0.1548 0.8040 0.129 Uiso 1 1 calc R U . . .
H7B3 H 0.0449 0.0964 0.8475 0.129 Uiso 1 1 calc R U . . .
H7B2 H 0.1664 0.1148 0.9329 0.129 Uiso 1 1 calc R U . . .
C9A C 0.4015(3) 0.2292(3) 1.1016(3) 0.0655(8) Uani 1 1 d . . . . .
H9A1 H 0.3408 0.2799 1.1373 0.079 Uiso 1 1 calc R U . . .
H9A2 H 0.3919 0.2537 1.0213 0.079 Uiso 1 1 calc R U . . .
C8B C 0.0097(3) 0.3014(6) 0.9949(3) 0.0947(13) Uani 1 1 d . . . . .
H8B2 H 0.0630 0.2733 1.0620 0.142 Uiso 1 1 calc R U . . .
H8B3 H -0.0612 0.2430 0.9836 0.142 Uiso 1 1 calc R U . . .
H8B1 H -0.0164 0.3934 1.0043 0.142 Uiso 1 1 calc R U . . .
C10A C 0.5283(2) 0.2700(3) 1.1556(2) 0.0554(7) Uani 1 1 d . . . . .
C9B C -0.0458(2) 0.5113(4) 0.4634(2) 0.0646(8) Uani 1 1 d . . . . .
H9B1 H -0.0181 0.6051 0.4658 0.077 Uiso 1 1 calc R U . . .
H9B2 H -0.1283 0.5088 0.4214 0.077 Uiso 1 1 calc R U . . .
C11A C 0.6257(3) 0.3248(4) 1.1125(3) 0.0733(9) Uani 1 1 d . . . . .
H11A H 0.6268 0.3471 1.0360 0.088 Uiso 1 1 calc R U . . .
C10B C 0.0378(2) 0.4287(3) 0.4016(2) 0.0472(6) Uani 1 1 d . . . . .
C11B C 0.0173(2) 0.3545(3) 0.3044(2) 0.0536(7) Uani 1 1 d . . . . .
H11B H -0.0583 0.3472 0.2584 0.064 Uiso 1 1 calc R U . . .
N1A N 0.56827(17) 0.2573(2) 1.26880(19) 0.0530(6) Uani 1 1 d . . . . .
N1B N 0.15925(16) 0.4093(2) 0.43663(17) 0.0480(5) Uani 1 1 d . . . . .
N2A N 0.68557(19) 0.3007(3) 1.2923(2) 0.0692(7) Uani 1 1 d . . . . .
N2B N 0.20916(18) 0.3254(3) 0.36603(18) 0.0564(6) Uani 1 1 d . . . . .
N3A N 0.7206(2) 0.3427(3) 1.1956(3) 0.0811(8) Uani 1 1 d . . . . .
N3B N 0.1220(2) 0.2930(3) 0.28383(19) 0.0590(6) Uani 1 1 d . . . . .
O1A O 0.3924(3) -0.2500(3) 1.3622(2) 0.0994(8) Uani 1 1 d . . . . .
O1B O 0.18494(17) 0.3787(2) 0.91200(17) 0.0707(6) Uani 1 1 d . . . . .
O2A O 0.38596(17) -0.1823(2) 1.17951(17) 0.0637(5) Uani 1 1 d . . . . .
O2B O 0.00464(15) 0.3468(2) 0.79394(15) 0.0552(5) Uani 1 1 d . . . . .
O3A O 0.37711(16) 0.0872(2) 1.11121(15) 0.0588(5) Uani 1 1 d . . . . .
O3B O -0.05070(14) 0.4650(2) 0.57778(15) 0.0612(6) Uani 1 1 d . . . . .
O4A O 0.41875(18) -0.0192(3) 1.40516(16) 0.0711(6) Uani 1 1 d . . . . .
O4B O 0.25004(15) 0.4593(2) 0.74393(15) 0.0613(5) Uani 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
C1A O1A 1.383(4) . ?
C1A O4A 1.420(4) . ?
C1A C2A 1.517(4) . ?
C1A H1A 0.9800 . ?
C2A O2A 1.418(4) . ?
C2A C3A 1.496(4) . ?
C2A H2A 0.9800 . ?
C1B O1B 1.379(4) . ?
C1B O4B 1.425(3) . ?
C1B C2B 1.519(4) . ?
C1B H1B 0.9800 . ?
C3A O3A 1.415(3) . ?
C3A C4A 1.520(3) . ?
C3A H3A 0.9800 . ?
C2B O2B 1.413(4) . ?
C2B C3B 1.504(4) . ?
C2B H2B 0.9800 . ?
C4A O4A 1.424(3) . ?
C4A C5A 1.511(4) . ?
C4A H4A 0.9800 . ?
C3B O3B 1.419(3) . ?
C3B C4B 1.526(3) . ?
C3B H3B 0.9800 . ?
C5A N1A 1.452(4) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C4B O4B 1.427(3) . ?
C4B C5B 1.500(4) . ?
C4B H4B 0.9800 . ?
C6A O1A 1.406(4) . ?
C6A O2A 1.427(4) . ?
C6A C7A 1.491(4) . ?
C6A C8A 1.514(5) . ?
C5B N1B 1.463(3) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C6B O2B 1.433(3) . ?
C6B O1B 1.439(3) . ?
C6B C8B 1.490(4) . ?
C6B C7B 1.494(5) . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 0.9600 . ?
C7B H7B1 0.9600 . ?
C7B H7B3 0.9600 . ?
C7B H7B2 0.9600 . ?
C9A O3A 1.429(4) . ?
C9A C10A 1.502(4) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C8B H8B2 0.9600 . ?
C8B H8B3 0.9600 . ?
C8B H8B1 0.9600 . ?
C10A C11A 1.351(4) . ?
C10A N1A 1.354(3) . ?
C9B O3B 1.432(3) . ?
C9B C10B 1.484(4) . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C11A N3A 1.341(4) . ?
C11A H11A 0.9300 . ?
C10B N1B 1.351(3) . ?
C10B C11B 1.353(4) . ?
C11B N3B 1.344(4) . ?
C11B H11B 0.9300 . ?
N1A N2A 1.345(3) . ?
N1B N2B 1.338(3) . ?
N2A N3A 1.316(4) . ?
N2B N3B 1.306(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
O1A C1A O4A 112.9(3) . . ?
O1A C1A C2A 105.3(3) . . ?
O4A C1A C2A 106.8(3) . . ?
O1A C1A H1A 110.6 . . ?
O4A C1A H1A 110.6 . . ?
C2A C1A H1A 110.6 . . ?
O2A C2A C3A 110.7(2) . . ?
O2A C2A C1A 103.0(2) . . ?
C3A C2A C1A 103.2(2) . . ?
O2A C2A H2A 113.0 . . ?
C3A C2A H2A 113.0 . . ?
C1A C2A H2A 113.0 . . ?
O1B C1B O4B 112.5(3) . . ?
O1B C1B C2B 105.5(2) . . ?
O4B C1B C2B 106.3(2) . . ?
O1B C1B H1B 110.8 . . ?
O4B C1B H1B 110.8 . . ?
C2B C1B H1B 110.8 . . ?
O3A C3A C2A 113.2(2) . . ?
O3A C3A C4A 115.20(19) . . ?
C2A C3A C4A 101.2(2) . . ?
O3A C3A H3A 109.0 . . ?
C2A C3A H3A 109.0 . . ?
C4A C3A H3A 109.0 . . ?
O2B C2B C3B 110.3(2) . . ?
O2B C2B C1B 103.3(2) . . ?
C3B C2B C1B 102.6(2) . . ?
O2B C2B H2B 113.3 . . ?
C3B C2B H2B 113.3 . . ?
C1B C2B H2B 113.3 . . ?
O4A C4A C5A 109.4(2) . . ?
O4A C4A C3A 102.42(19) . . ?
C5A C4A C3A 115.0(2) . . ?
O4A C4A H4A 109.9 . . ?
C5A C4A H4A 109.9 . . ?
C3A C4A H4A 109.9 . . ?
O3B C3B C2B 113.1(2) . . ?
O3B C3B C4B 115.4(2) . . ?
C2B C3B C4B 101.1(2) . . ?
O3B C3B H3B 109.0 . . ?
C2B C3B H3B 109.0 . . ?
C4B C3B H3B 109.0 . . ?
N1A C5A C4A 108.7(2) . . ?
N1A C5A H5A1 109.9 . . ?
C4A C5A H5A1 109.9 . . ?
N1A C5A H5A2 109.9 . . ?
C4A C5A H5A2 109.9 . . ?
H5A1 C5A H5A2 108.3 . . ?
O4B C4B C5B 109.80(19) . . ?
O4B C4B C3B 101.94(19) . . ?
C5B C4B C3B 114.5(2) . . ?
O4B C4B H4B 110.1 . . ?
C5B C4B H4B 110.1 . . ?
C3B C4B H4B 110.1 . . ?
O1A C6A O2A 105.0(3) . . ?
O1A C6A C7A 111.0(3) . . ?
O2A C6A C7A 108.6(3) . . ?
O1A C6A C8A 109.1(3) . . ?
O2A C6A C8A 109.6(3) . . ?
C7A C6A C8A 113.2(4) . . ?
N1B C5B C4B 108.48(19) . . ?
N1B C5B H5B1 110.0 . . ?
C4B C5B H5B1 110.0 . . ?
N1B C5B H5B2 110.0 . . ?
C4B C5B H5B2 110.0 . . ?
H5B1 C5B H5B2 108.4 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
O2B C6B O1B 105.2(2) . . ?
O2B C6B C8B 110.7(2) . . ?
O1B C6B C8B 109.1(3) . . ?
O2B C6B C7B 108.4(2) . . ?
O1B C6B C7B 109.1(2) . . ?
C8B C6B C7B 113.9(3) . . ?
C6A C8A H8A1 109.5 . . ?
C6A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
H7B3 C7B H7B2 109.5 . . ?
O3A C9A C10A 113.5(2) . . ?
O3A C9A H9A1 108.9 . . ?
C10A C9A H9A1 108.9 . . ?
O3A C9A H9A2 108.9 . . ?
C10A C9A H9A2 108.9 . . ?
H9A1 C9A H9A2 107.7 . . ?
C6B C8B H8B2 109.5 . . ?
C6B C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C6B C8B H8B1 109.5 . . ?
H8B2 C8B H8B1 109.5 . . ?
H8B3 C8B H8B1 109.5 . . ?
C11A C10A N1A 103.9(2) . . ?
C11A C10A C9A 132.5(3) . . ?
N1A C10A C9A 123.6(3) . . ?
O3B C9B C10B 112.9(2) . . ?
O3B C9B H9B1 109.0 . . ?
C10B C9B H9B1 109.0 . . ?
O3B C9B H9B2 109.0 . . ?
C10B C9B H9B2 109.0 . . ?
H9B1 C9B H9B2 107.8 . . ?
N3A C11A C10A 110.4(3) . . ?
N3A C11A H11A 124.8 . . ?
C10A C11A H11A 124.8 . . ?
N1B C10B C11B 103.3(2) . . ?
N1B C10B C9B 124.8(2) . . ?
C11B C10B C9B 131.9(2) . . ?
N3B C11B C10B 110.2(2) . . ?
N3B C11B H11B 124.9 . . ?
C10B C11B H11B 124.9 . . ?
N2A N1A C10A 110.4(2) . . ?
N2A N1A C5A 121.2(2) . . ?
C10A N1A C5A 128.0(2) . . ?
N2B N1B C10B 111.2(2) . . ?
N2B N1B C5B 119.82(19) . . ?
C10B N1B C5B 128.9(2) . . ?
N3A N2A N1A 107.4(2) . . ?
N3B N2B N1B 107.17(19) . . ?
N2A N3A C11A 107.9(2) . . ?
N2B N3B C11B 108.2(2) . . ?
C1A O1A C6A 111.4(3) . . ?
C1B O1B C6B 110.5(2) . . ?
C2A O2A C6A 108.1(2) . . ?
C2B O2B C6B 108.8(2) . . ?
C3A O3A C9A 112.0(2) . . ?
C3B O3B C9B 111.8(2) . . ?
C1A O4A C4A 108.3(2) . . ?
C1B O4B C4B 109.51(17) . . ?

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
C1A H1A O3B 0.98 2.54 3.438(3) 152.8 2_547
C2A H2A O2B 0.98 2.52 3.449(3) 158.1 2_547
C3A H3A N3B 0.98 2.62 3.600(3) 173.8 1_556
C4A H4A O4B 0.98 2.50 3.424(3) 156.9 2_647
C5A H5A1 N2B 0.97 2.58 3.508(3) 160.1 1_556
C5A H5A2 O1A 0.97 2.56 3.413(4) 147.4 2_658
C8A H8A1 N2B 0.96 2.63 3.446(5) 142.9 1_546
C8B H8B2 N3B 0.96 2.62 3.469(4) 147.8 1_556
C11A H11A O2A 0.93 2.54 3.431(4) 159.5 2_657
C11B H11B N3A 0.93 2.43 3.329(3) 161.8 1_454
C1A H1A O3B 0.98 2.54 3.438(3) 152.8 2_547
C2A H2A O2B 0.98 2.52 3.449(3) 158.1 2_547
C3A H3A N3B 0.98 2.62 3.600(3) 173.8 1_556
C4A H4A O4B 0.98 2.50 3.424(3) 156.9 2_647
C5A H5A1 N2B 0.97 2.58 3.508(3) 160.1 1_556
C5A H5A2 O1A 0.97 2.56 3.413(4) 147.4 2_658
C8A H8A1 N2B 0.96 2.63 3.446(5) 142.9 1_546
C8B H8B2 N3B 0.96 2.62 3.469(4) 147.8 1_556
C11A H11A O2A 0.93 2.54 3.431(4) 159.5 2_657
C11B H11B N3A 0.93 2.43 3.329(3) 161.8 1_454

_refine_diff_density_max         0.097
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030

_shelxl_version_number           2014-3

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

data_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1574974'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N6 O8, 0.630(H) 0.315(O)'
_chemical_formula_sum            'C22 H30.63 N6 O8.32'
_chemical_formula_weight         512.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.4430(2)
_cell_length_b                   21.1577(6)
_cell_length_c                   21.2367(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2445.65(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7922
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      24.15

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.392
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1085
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            18861
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4302
_reflns_number_gt                3646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT 2013/5 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0480P)²+0.0569P] 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_abs_structure_details 
;
 Flack x determined using 1332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(5)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         4302
_refine_ls_number_parameters     329
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      5.623
_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
C1 C 0.2047(5) 0.64123(12) 0.30416(14) 0.0459(7) Uani 1 1 d . . . . .
H1 H 0.283179 0.602849 0.320375 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3862(5) 0.69559(12) 0.29940(13) 0.0431(7) Uani 1 1 d . . . . .
H2 H 0.555441 0.681627 0.306851 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3505(5) 0.72050(11) 0.23184(13) 0.0389(6) Uani 1 1 d . . . . .
H3 H 0.484809 0.705644 0.204903 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1094(5) 0.69018(12) 0.21123(13) 0.0406(6) Uani 1 1 d . . . . .
H4 H -0.029052 0.716638 0.224484 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0873(6) 0.67510(13) 0.14160(13) 0.0513(7) Uani 1 1 d . . . . .
H5A H 0.215425 0.645508 0.129836 0.062 Uiso 1 1 calc R U . . .
H5B H -0.069991 0.655045 0.133736 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1211(6) 0.71412(13) 0.38151(13) 0.0472(7) Uani 1 1 d . . . . .
C7 C -0.0729(7) 0.76355(18) 0.3906(2) 0.0827(12) Uani 1 1 d . . . . .
H7A H -0.203167 0.746701 0.415999 0.124 Uiso 1 1 calc R U . . .
H7B H -0.002678 0.799673 0.411138 0.124 Uiso 1 1 calc R U . . .
H7C H -0.137235 0.775933 0.350306 0.124 Uiso 1 1 calc R U . . .
C8 C 0.2244(9) 0.69003(19) 0.44240(17) 0.0897(13) Uani 1 1 d . . . . .
H8A H 0.094442 0.672554 0.467507 0.135 Uiso 1 1 calc R U . . .
H8B H 0.344406 0.657889 0.433872 0.135 Uiso 1 1 calc R U . . .
H8C H 0.300627 0.724217 0.464801 0.135 Uiso 1 1 calc R U . . .
C9 C 0.5451(5) 0.82049(12) 0.23456(14) 0.0406(6) Uani 1 1 d . . . . .
H9A H 0.675601 0.802567 0.209077 0.049 Uiso 1 1 calc R U . . .
H9B H 0.595420 0.819296 0.278365 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4944(4) 0.88646(11) 0.21489(12) 0.0343(6) Uani 1 1 d . . . . .
C11 C 0.2848(5) 0.91137(11) 0.19124(12) 0.0380(6) Uani 1 1 d . . . . .
H11 H 0.136406 0.890701 0.184393 0.046 Uiso 1 1 calc R U . . .
C12 C 0.4889(6) 1.02795(16) -0.00203(15) 0.0599(9) Uani 1 1 d . . . . .
H12 H 0.663057 1.017745 -0.007831 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3264(6) 0.97156(15) -0.01727(14) 0.0568(8) Uani 1 1 d . . . . .
H13 H 0.418717 0.936048 -0.035088 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2085(5) 0.95560(12) 0.04563(13) 0.0444(7) Uani 1 1 d . . . . .
H14 H 0.316248 0.926649 0.068764 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2070(5) 1.01930(12) 0.07856(13) 0.0447(7) Uani 1 1 d . . . . .
H15 H 0.075574 1.045369 0.060648 0.054 Uiso 1 1 calc R U . . .
C16 C 0.1824(5) 1.01894(12) 0.14951(13) 0.0427(6) Uani 1 1 d . . . . .
H16A H 0.224458 1.060477 0.165555 0.051 Uiso 1 1 calc R U . . .
H16B H 0.012386 1.010650 0.160476 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2536(7) 1.04915(18) -0.08992(16) 0.0694(10) Uani 1 1 d . . . . .
C18 C 0.0536(8) 1.0952(2) -0.1046(2) 0.0907(13) Uani 1 1 d . . . . .
H18A H 0.122277 1.131564 -0.125169 0.136 Uiso 1 1 calc R U . . .
H18B H -0.065013 1.075664 -0.131750 0.136 Uiso 1 1 calc R U . . .
H18C H -0.025047 1.108131 -0.066191 0.136 Uiso 1 1 calc R U . . .
C19 C 0.3957(10) 1.0297(3) -0.14784(19) 0.1207(19) Uani 1 1 d . . . . .
H19A H 0.465114 1.066514 -0.167408 0.181 Uiso 1 1 calc R U . . .
H19B H 0.525074 1.001251 -0.136016 0.181 Uiso 1 1 calc R U . . .
H19C H 0.287236 1.009027 -0.176922 0.181 Uiso 1 1 calc R U . . .
C20 C -0.0526(7) 0.87063(13) 0.01449(15) 0.0583(8) Uani 1 1 d . . . . .
H20A H 0.028698 0.872990 -0.026092 0.070 Uiso 1 1 calc R U . . .
H20B H -0.225079 0.862133 0.006788 0.070 Uiso 1 1 calc R U . . .
C21 C 0.0528(5) 0.81671(13) 0.05025(13) 0.0447(7) Uani 1 1 d . . . . .
C22 C -0.0662(5) 0.77108(13) 0.08334(13) 0.0475(7) Uani 1 1 d . . . . .
H22 H -0.234210 0.768156 0.090745 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1077(4) 0.73140(10) 0.10300(11) 0.0442(6) Uani 1 1 d . . . . .
N2 N 0.3302(4) 0.75142(11) 0.08377(11) 0.0501(6) Uani 1 1 d . . . . .
N3 N 0.2961(5) 0.80306(11) 0.05120(11) 0.0517(6) Uani 1 1 d . . . . .
N4 N 0.3369(4) 0.97230(9) 0.17977(10) 0.0370(5) Uani 1 1 d . . . . .
N5 N 0.5686(4) 0.98486(11) 0.19640(13) 0.0557(7) Uani 1 1 d . . . . .
N6 N 0.6648(5) 0.93215(10) 0.21779(13) 0.0561(7) Uani 1 1 d . . . . .
O1 O 0.0247(4) 0.66356(10) 0.34523(11) 0.0584(6) Uani 1 1 d . . . . .
O2 O 0.3099(4) 0.73996(9) 0.34406(10) 0.0588(6) Uani 1 1 d . . . . .
O3 O 0.3257(3) 0.78606(7) 0.22613(9) 0.0429(4) Uani 1 1 d . . . . .
O4 O 0.1028(4) 0.63136(8) 0.24400(9) 0.0513(5) Uani 1 1 d . . . . .
O5 O 0.4135(5) 1.07566(12) -0.04348(12) 0.0769(7) Uani 1 1 d . . . . .
O6 O 0.1475(4) 0.99579(11) -0.05944(10) 0.0667(6) Uani 1 1 d D . . . .
O7 O -0.0317(4) 0.93057(9) 0.04469(10) 0.0533(5) Uani 1 1 d . . . . .
O8 O 0.4388(4) 1.04538(9) 0.06081(10) 0.0558(6) Uani 1 1 d . . . . .
O1' O 0.528(2) 0.5864(6) 0.1613(6) 0.131(4) Uiso 0.3155 1 d D . P . .


_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 O1 1.394(4) . ?
C1 O4 1.408(3) . ?
C1 C2 1.519(4) . ?
C1 H1 0.9800 . ?
C2 O2 1.398(3) . ?
C2 C3 1.541(4) . ?
C2 H2 0.9800 . ?
C3 O3 1.399(3) . ?
C3 C4 1.525(4) . ?
C3 H3 0.9800 . ?
C4 O4 1.426(3) . ?
C4 C5 1.518(4) . ?
C4 H4 0.9800 . ?
C5 N1 1.450(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O2 1.410(4) . ?
C6 O1 1.419(3) . ?
C6 C7 1.499(5) . ?
C6 C8 1.499(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.411(3) . ?
C9 C10 1.483(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N6 1.341(3) . ?
C10 C11 1.353(4) . ?
C11 N4 1.342(3) . ?
C11 H11 0.9300 . ?
C12 O5 1.401(4) . ?
C12 O8 1.411(4) . ?
C12 C13 1.520(5) . ?
C12 H12 0.9800 . ?
C13 O6 1.419(4) . ?
C13 C14 1.520(4) . ?
C13 H13 0.9800 . ?
C14 O7 1.411(3) . ?
C14 C15 1.518(4) . ?
C14 H14 0.9800 . ?
C15 O8 1.428(3) . ?
C15 C16 1.513(4) . ?
C15 H15 0.9800 . ?
C16 N4 1.447(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O6 1.424(4) . ?
C17 O5 1.430(4) . ?
C17 C18 1.495(5) . ?
C17 C19 1.510(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O7 1.426(3) . ?
C20 C21 1.486(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N3 1.356(4) . ?
C21 C22 1.358(4) . ?
C22 N1 1.332(4) . ?
C22 H22 0.9300 . ?
N1 N2 1.346(3) . ?
N2 N3 1.306(3) . ?
N4 N5 1.337(3) . ?
N5 N6 1.313(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
O1 C1 O4 109.9(2) . . ?
O1 C1 C2 104.0(2) . . ?
O4 C1 C2 107.9(2) . . ?
O1 C1 H1 111.5 . . ?
O4 C1 H1 111.5 . . ?
C2 C1 H1 111.5 . . ?
O2 C2 C1 105.7(2) . . ?
O2 C2 C3 111.4(2) . . ?
C1 C2 C3 103.8(2) . . ?
O2 C2 H2 111.8 . . ?
C1 C2 H2 111.8 . . ?
C3 C2 H2 111.8 . . ?
O3 C3 C4 108.0(2) . . ?
O3 C3 C2 115.6(2) . . ?
C4 C3 C2 103.4(2) . . ?
O3 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
O4 C4 C5 106.9(2) . . ?
O4 C4 C3 104.4(2) . . ?
C5 C4 C3 115.9(2) . . ?
O4 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
N1 C5 C4 111.8(2) . . ?
N1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 O1 104.8(2) . . ?
O2 C6 C7 108.4(3) . . ?
O1 C6 C7 109.6(3) . . ?
O2 C6 C8 110.2(3) . . ?
O1 C6 C8 110.5(3) . . ?
C7 C6 C8 113.0(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C10 107.0(2) . . ?
O3 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N6 C10 C11 108.6(2) . . ?
N6 C10 C9 122.5(2) . . ?
C11 C10 C9 128.9(2) . . ?
N4 C11 C10 105.3(2) . . ?
N4 C11 H11 127.4 . . ?
C10 C11 H11 127.4 . . ?
O5 C12 O8 110.4(3) . . ?
O5 C12 C13 105.1(2) . . ?
O8 C12 C13 107.1(2) . . ?
O5 C12 H12 111.3 . . ?
O8 C12 H12 111.3 . . ?
C13 C12 H12 111.3 . . ?
O6 C13 C12 104.5(2) . . ?
O6 C13 C14 110.2(3) . . ?
C12 C13 C14 103.5(2) . . ?
O6 C13 H13 112.7 . . ?
C12 C13 H13 112.7 . . ?
C14 C13 H13 112.7 . . ?
O7 C14 C15 109.5(2) . . ?
O7 C14 C13 117.5(2) . . ?
C15 C14 C13 102.1(2) . . ?
O7 C14 H14 109.1 . . ?
C15 C14 H14 109.1 . . ?
C13 C14 H14 109.1 . . ?
O8 C15 C16 110.1(2) . . ?
O8 C15 C14 102.5(2) . . ?
C16 C15 C14 117.1(2) . . ?
O8 C15 H15 109.0 . . ?
C16 C15 H15 109.0 . . ?
C14 C15 H15 109.0 . . ?
N4 C16 C15 113.2(2) . . ?
N4 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
N4 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
O6 C17 O5 104.2(2) . . ?
O6 C17 C18 108.4(3) . . ?
O5 C17 C18 109.3(3) . . ?
O6 C17 C19 111.2(4) . . ?
O5 C17 C19 110.9(3) . . ?
C18 C17 C19 112.4(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C20 C21 115.0(2) . . ?
O7 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
O7 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
N3 C21 C22 107.9(3) . . ?
N3 C21 C20 123.3(3) . . ?
C22 C21 C20 128.8(3) . . ?
N1 C22 C21 105.7(3) . . ?
N1 C22 H22 127.1 . . ?
C21 C22 H22 127.1 . . ?
C22 N1 N2 110.2(2) . . ?
C22 N1 C5 129.8(2) . . ?
N2 N1 C5 119.9(2) . . ?
N3 N2 N1 107.2(2) . . ?
N2 N3 C21 108.9(3) . . ?
N5 N4 C11 110.0(2) . . ?
N5 N4 C16 122.0(2) . . ?
C11 N4 C16 127.8(2) . . ?
N6 N5 N4 107.4(2) . . ?
N5 N6 C10 108.7(2) . . ?
C1 O1 C6 109.6(2) . . ?
C2 O2 C6 109.8(2) . . ?
C3 O3 C9 114.8(2) . . ?
C1 O4 C4 107.66(19) . . ?
C12 O5 C17 109.2(3) . . ?
C13 O6 C17 107.2(3) . . ?
C14 O7 C20 114.4(2) . . ?
C12 O8 C15 108.6(2) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034

