# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_2017585_0m
_database_code_depnum_ccdc_archive 'CCDC 1860886'
loop_
_audit_author_name
_audit_author_address
'Zai-Yong Zhang'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 O4, C4 H12 N5'
_chemical_formula_sum            'C13 H19 N5 O4'
_chemical_formula_weight         309.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.982(4)
_cell_length_b                   10.918(3)
_cell_length_c                   15.273(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.315(5)
_cell_angle_gamma                90
_cell_volume                     1589.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1398
_cell_measurement_temperature    205
_cell_measurement_theta_max      21.84
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1120 before and 0.0653 after correction. The Ratio of minimum to maximum transmission is 0.7971. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13789
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.177
_diffrn_ambient_temperature      205.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2258
_reflns_number_total             3610
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13-N5 = C13-H13A = C13-H13B = C13-H13C
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.66911(12) 0.59650(13) 0.58363(9) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.62015(13) 0.77216(12) 0.70060(9) 0.0349(3) Uani 1 1 d . . . . .
O4 O 0.89139(13) 0.55365(15) 0.59794(10) 0.0496(4) Uani 1 1 d . . . . .
O1 O 0.68792(15) 0.90764(15) 0.61084(11) 0.0499(4) Uani 1 1 d . . . . .
N2 N 0.39398(17) 0.53945(16) 0.58815(12) 0.0322(4) Uani 1 1 d . . . . .
N1 N 0.16365(15) 0.56049(16) 0.57650(11) 0.0347(4) Uani 1 1 d . . . . .
H1A H 0.144004 0.535876 0.519906 0.042 Uiso 1 1 calc R . . . .
H1B H 0.096286 0.579172 0.599448 0.042 Uiso 1 1 calc R . . . .
N3 N 0.32162(15) 0.61354(15) 0.71350(11) 0.0333(4) Uani 1 1 d . . . . .
N5 N 0.47410(17) 0.65634(16) 0.85541(11) 0.0393(4) Uani 1 1 d D . . . .
N4 N 0.5128(2) 0.48258(18) 0.78171(13) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.29625(18) 0.56955(16) 0.62777(13) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.79693(18) 0.60323(17) 0.62467(13) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.76086(19) 0.74735(17) 0.75017(13) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.84512(18) 0.66940(17) 0.71619(12) 0.0269(4) Uani 1 1 d . . . . .
C11 C 0.43713(19) 0.58473(18) 0.78045(13) 0.0317(4) Uani 1 1 d . . . . .
C5 C 0.98142(19) 0.65011(18) 0.77289(12) 0.0328(5) Uani 1 1 d . . . . .
H5 H 1.041886 0.599713 0.751997 0.039 Uiso 1 1 calc R . . . .
C9 C 0.5960(2) 0.85615(18) 0.63237(14) 0.0355(5) Uani 1 1 d . . . . .
C2 C 0.8091(2) 0.80172(19) 0.83557(14) 0.0372(5) Uani 1 1 d . . . . .
H2 H 0.750135 0.854198 0.856168 0.045 Uiso 1 1 calc R . . . .
C4 C 1.0307(2) 0.7030(2) 0.85929(13) 0.0408(5) Uani 1 1 d . . . . .
H4 H 1.122702 0.687383 0.896371 0.049 Uiso 1 1 calc R . . . .
C3 C 0.9436(2) 0.77889(19) 0.89042(14) 0.0412(5) Uani 1 1 d . . . . .
H3 H 0.976076 0.814769 0.948887 0.049 Uiso 1 1 calc R . . . .
C8 C 0.4421(2) 0.8747(2) 0.59035(16) 0.0442(6) Uani 1 1 d . . . . .
H8A H 0.399428 0.798513 0.563058 0.066 Uiso 1 1 calc GR . . . .
H8B H 0.426384 0.937369 0.543386 0.066 Uiso 1 1 calc GR . . . .
H8C H 0.400536 0.900137 0.637290 0.066 Uiso 1 1 calc GR . . . .
C12 C 0.4074(2) 0.7753(2) 0.85614(17) 0.0515(6) Uani 1 1 d . . . . .
H12A H 0.473901 0.840004 0.855820 0.077 Uiso 1 1 calc GR . . . .
H12B H 0.377589 0.782269 0.910851 0.077 Uiso 1 1 calc GR . . . .
H12C H 0.326521 0.782697 0.802223 0.077 Uiso 1 1 calc GR . . . .
C13 C 0.5892(2) 0.6253(2) 0.93550(14) 0.0505(6) Uani 1 1 d D . . . .
H13A H 0.576392 0.542753 0.955035 0.076 Uiso 1 1 calc DGR . . . .
H13B H 0.591400 0.682344 0.984627 0.076 Uiso 1 1 calc DGR . . . .
H13C H 0.676904 0.630129 0.920535 0.076 Uiso 1 1 calc DGR . . . .
H2A H 0.3695(19) 0.5045(18) 0.5310(14) 0.032(5) Uiso 1 1 d . . . . .
H2B H 0.482(2) 0.563(2) 0.6097(15) 0.052(7) Uiso 1 1 d . . . . .
H4A H 0.592(2) 0.468(2) 0.8221(16) 0.048(7) Uiso 1 1 d . . . . .
H4B H 0.487(2) 0.435(2) 0.7318(16) 0.049(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
O3 C7 1.245(2) . ?
O2 C1 1.409(2) . ?
O2 C9 1.355(2) . ?
O4 C7 1.256(2) . ?
O1 C9 1.203(2) . ?
N2 C10 1.333(2) . ?
N2 H2A 0.92(2) . ?
N2 H2B 0.88(2) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C10 1.326(2) . ?
N3 C10 1.346(2) . ?
N3 C11 1.331(2) . ?
N5 C11 1.344(2) . ?
N5 C12 1.461(3) . ?
N5 C13 1.447(3) . ?
N4 C11 1.344(3) . ?
N4 H4A 0.86(2) . ?
N4 H4B 0.90(2) . ?
C7 C6 1.519(3) . ?
C1 C6 1.400(3) . ?
C1 C2 1.383(3) . ?
C6 C5 1.394(2) . ?
C5 H5 0.9400 . ?
C5 C4 1.389(3) . ?
C9 C8 1.491(3) . ?
C2 H2 0.9400 . ?
C2 C3 1.377(3) . ?
C4 H4 0.9400 . ?
C4 C3 1.384(3) . ?
C3 H3 0.9400 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?

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
C9 O2 C1 117.65(15) . . ?
C10 N2 H2A 120.7(11) . . ?
C10 N2 H2B 123.0(14) . . ?
H2A N2 H2B 115.4(18) . . ?
H1A N1 H1B 120.0 . . ?
C10 N1 H1A 120.0 . . ?
C10 N1 H1B 120.0 . . ?
C11 N3 C10 122.14(16) . . ?
C11 N5 C12 120.89(17) . . ?
C11 N5 C13 122.11(18) . . ?
C13 N5 C12 116.77(17) . . ?
C11 N4 H4A 124.0(15) . . ?
C11 N4 H4B 117.0(14) . . ?
H4A N4 H4B 118(2) . . ?
N2 C10 N3 125.33(16) . . ?
N1 C10 N2 116.76(17) . . ?
N1 C10 N3 117.83(16) . . ?
O3 C7 O4 124.52(17) . . ?
O3 C7 C6 119.20(16) . . ?
O4 C7 C6 116.19(15) . . ?
C6 C1 O2 122.03(16) . . ?
C2 C1 O2 115.83(17) . . ?
C2 C1 C6 122.12(18) . . ?
C1 C6 C7 124.71(16) . . ?
C5 C6 C7 118.88(17) . . ?
C5 C6 C1 116.38(17) . . ?
N3 C11 N5 118.18(18) . . ?
N3 C11 N4 124.19(18) . . ?
N4 C11 N5 117.37(17) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.09(19) . . ?
C4 C5 H5 119.0 . . ?
O2 C9 C8 110.34(17) . . ?
O1 C9 O2 123.44(18) . . ?
O1 C9 C8 126.2(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.60(19) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 119.86(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
_geom_hbond_publ_flag
N1 H1A O4 0.87 1.99 2.843(2) 168.4 3_666 yes
N1 H1B O4 0.87 2.06 2.834(2) 148.1 1_455 yes
N2 H2B O3 0.88(2) 2.05(2) 2.837(2) 147.6(19) . yes

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

data_20180326_a
_database_code_depnum_ccdc_archive 'CCDC 1860888'
loop_
_audit_author_name
_audit_author_address
'Zai-Yong Zhang' 'Shanghai Institute of Materia Medica'
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
_audit_creation_date             2018-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H7 O4), 2(C4 H12 N5), H2 O'
_chemical_formula_sum            'C26 H40 N10 O9'
_chemical_formula_weight         636.68
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0858(9)
_cell_length_b                   11.9718(12)
_cell_length_c                   16.5784(17)
_cell_angle_alpha                69.9000(10)
_cell_angle_beta                 75.107(2)
_cell_angle_gamma                67.877(3)
_cell_volume                     1551.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    205(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      4.28
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2014
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14201
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.322
_diffrn_ambient_temperature      205.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4046
_reflns_number_total             6965
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6965
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H,H) groups
2. Restrained distances
 N4'-H4'A \\sim N4'-H4'B \\sim N1'-H1'A
 with sigma of 0.02
 N4-H4A \\sim N4-H4B \\sim N1-H1B
 with sigma of 0.02
3.a Free rotating group:
 O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C5'(H5'), C2(H2), C4(H4), C4'(H4'), C2'(H2'), C3(H3), C3'(H3')
3.c X=CH2 refined with riding coordinates:
 N1'(H1'A,H1'B), N2'(H2'A,H2'B), N2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C13'(H13D,H13E,H13F), C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F), C8(H8A,H8B,
 H8C), C13(H13A,H13B,H13C), C8'(H8'A,H8'B,H8'C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3' O 0.26276(17) 0.45402(15) 0.97518(10) 0.0330(4) Uani 1 1 d . . . . .
O2' O 0.31558(19) 0.19674(15) 1.01457(10) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.95371(19) 0.71694(15) 0.27446(10) 0.0352(4) Uani 1 1 d . . . . .
O4 O 0.82025(18) 0.94980(15) 0.43002(10) 0.0332(4) Uani 1 1 d . . . . .
O3 O 0.69866(18) 0.87098(16) 0.37283(10) 0.0379(4) Uani 1 1 d . . . . .
O4' O 0.47364(19) 0.48824(16) 0.87917(10) 0.0384(4) Uani 1 1 d . . . . .
O1 O 1.0316(2) 0.64824(16) 0.40600(11) 0.0396(4) Uani 1 1 d . . . . .
N3 N 0.2832(2) 0.72336(17) 0.57781(11) 0.0275(4) Uani 1 1 d . . . . .
O1' O 0.3897(2) 0.23714(18) 0.86956(11) 0.0449(5) Uani 1 1 d . . . . .
N3' N 0.9162(2) 0.69775(17) 0.75309(11) 0.0261(4) Uani 1 1 d . . . . .
N4 N 0.4519(2) 0.84937(18) 0.51716(12) 0.0271(4) Uani 1 1 d D . . . .
N5' N 0.6474(2) 0.77216(17) 0.74003(12) 0.0260(4) Uani 1 1 d . . . . .
N5 N 0.5574(2) 0.63548(17) 0.57120(12) 0.0295(5) Uani 1 1 d . . . . .
O5 O 0.5083(2) 0.7793(2) 0.32216(12) 0.0510(5) Uani 1 1 d . . . . .
H5A H 0.533507 0.767751 0.271292 0.076 Uiso 1 1 d G . . . .
H5B H 0.579757 0.808069 0.325183 0.076 Uiso 1 1 d G . . . .
N4' N 0.7537(2) 0.56622(19) 0.81575(13) 0.0318(5) Uani 1 1 d D . . . .
N1' N 0.9967(2) 0.58839(19) 0.89152(12) 0.0342(5) Uani 1 1 d D . . . .
H1'A H 1.074592 0.552316 0.922577 0.041 Uiso 1 1 calc DR . . . .
H1'B H 0.898513 0.593203 0.916291 0.041 Uiso 1 1 calc R . . . .
N2' N 1.1805(2) 0.62589(18) 0.77201(12) 0.0315(5) Uani 1 1 d . . . . .
H2'A H 1.255165 0.589145 0.805194 0.038 Uiso 1 1 calc R . . . .
H2'B H 1.205475 0.656026 0.716409 0.038 Uiso 1 1 calc R . . . .
N2 N 0.0164(2) 0.80885(19) 0.56304(12) 0.0358(5) Uani 1 1 d . . . . .
H2A H -0.060034 0.851009 0.531205 0.043 Uiso 1 1 calc R . . . .
H2B H -0.006871 0.776623 0.618509 0.043 Uiso 1 1 calc R . . . .
N1 N 0.1962(3) 0.8453(2) 0.44171(13) 0.0361(5) Uani 1 1 d D . . . .
H1A H 0.118(3) 0.884(3) 0.4146(18) 0.054 Uiso 1 1 d R . . . .
C11 C 0.4301(3) 0.7369(2) 0.55269(13) 0.0235(5) Uani 1 1 d . . . . .
C11' C 0.7724(2) 0.6789(2) 0.77233(13) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.8083(2) 0.9111(2) 0.37135(14) 0.0255(5) Uani 1 1 d . . . . .
C10' C 1.0276(2) 0.6360(2) 0.80643(14) 0.0239(5) Uani 1 1 d . . . . .
C6' C 0.5140(2) 0.2991(2) 0.99356(13) 0.0252(5) Uani 1 1 d . . . . .
C1 C 1.0075(3) 0.8213(2) 0.25119(15) 0.0294(5) Uani 1 1 d . . . . .
C6 C 0.9362(2) 0.9162(2) 0.29235(13) 0.0234(5) Uani 1 1 d . . . . .
C10 C 0.1686(3) 0.7937(2) 0.52695(14) 0.0270(5) Uani 1 1 d . . . . .
C7' C 0.4100(3) 0.4234(2) 0.94467(14) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.9662(3) 0.6380(2) 0.35604(16) 0.0311(5) Uani 1 1 d . . . . .
C1' C 0.4642(3) 0.1930(2) 1.02694(14) 0.0288(5) Uani 1 1 d . . . . .
C9' C 0.2874(3) 0.2287(2) 0.93133(16) 0.0344(6) Uani 1 1 d . . . . .
C13' C 0.4943(3) 0.7529(2) 0.74770(15) 0.0332(6) Uani 1 1 d . . . . .
H13D H 0.512952 0.680450 0.728118 0.050 Uiso 1 1 calc GR . . . .
H13E H 0.424474 0.826586 0.712196 0.050 Uiso 1 1 calc GR . . . .
H13F H 0.443919 0.738862 0.807864 0.050 Uiso 1 1 calc GR . . . .
C5 C 0.9906(3) 1.0200(2) 0.25934(14) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.946945 1.085086 0.286443 0.036 Uiso 1 1 calc R . . . .
C12 C 0.7139(3) 0.6443(2) 0.56990(16) 0.0362(6) Uani 1 1 d . . . . .
H12A H 0.789065 0.614604 0.522592 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.752861 0.593080 0.624524 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.703811 0.730898 0.561711 0.054 Uiso 1 1 calc GR . . . .
C5' C 0.6622(3) 0.2868(3) 1.01087(15) 0.0343(6) Uani 1 1 d . . . . .
H5' H 0.701747 0.355275 0.987867 0.041 Uiso 1 1 calc R . . . .
C2 C 1.1303(3) 0.8270(3) 0.18146(16) 0.0408(6) Uani 1 1 d . . . . .
H2 H 1.179580 0.759808 0.156331 0.049 Uiso 1 1 calc R . . . .
C4 C 1.1078(3) 1.0287(3) 0.18735(15) 0.0384(6) Uani 1 1 d . . . . .
H4 H 1.138805 1.101368 0.164173 0.046 Uiso 1 1 calc R . . . .
C12' C 0.6544(3) 0.8991(2) 0.69547(17) 0.0396(6) Uani 1 1 d . . . . .
H12D H 0.754122 0.904946 0.701973 0.059 Uiso 1 1 calc GR . . . .
H12E H 0.564368 0.958701 0.720572 0.059 Uiso 1 1 calc GR . . . .
H12F H 0.649279 0.917883 0.634295 0.059 Uiso 1 1 calc GR . . . .
C4' C 0.7528(3) 0.1744(3) 1.06179(16) 0.0463(7) Uani 1 1 d . . . . .
H4' H 0.852092 0.168045 1.073416 0.056 Uiso 1 1 calc R . . . .
C2' C 0.5539(3) 0.0809(2) 1.07743(16) 0.0412(6) Uani 1 1 d . . . . .
H2' H 0.516934 0.011112 1.099378 0.049 Uiso 1 1 calc R . . . .
C8 C 0.8877(3) 0.5414(2) 0.37198(18) 0.0419(6) Uani 1 1 d . . . . .
H8A H 0.772102 0.580518 0.377283 0.063 Uiso 1 1 calc GR . . . .
H8B H 0.915523 0.476584 0.425209 0.063 Uiso 1 1 calc GR . . . .
H8C H 0.924540 0.504350 0.323803 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.5436(3) 0.5087(2) 0.60557(18) 0.0450(7) Uani 1 1 d . . . . .
H13A H 0.534439 0.483599 0.668391 0.068 Uiso 1 1 calc GR . . . .
H13B H 0.638292 0.450484 0.582081 0.068 Uiso 1 1 calc GR . . . .
H13C H 0.448923 0.508411 0.588964 0.068 Uiso 1 1 calc GR . . . .
C3 C 1.1791(3) 0.9314(3) 0.14951(16) 0.0435(7) Uani 1 1 d . . . . .
H3 H 1.261246 0.936559 0.101812 0.052 Uiso 1 1 calc R . . . .
C3' C 0.6977(3) 0.0734(3) 1.09491(17) 0.0500(8) Uani 1 1 d . . . . .
H3' H 0.758758 -0.001694 1.129880 0.060 Uiso 1 1 calc R . . . .
C8' C 0.1159(3) 0.2472(3) 0.9303(2) 0.0521(8) Uani 1 1 d . . . . .
H8'A H 0.093211 0.168911 0.960489 0.078 Uiso 1 1 calc GR . . . .
H8'B H 0.096397 0.273549 0.870711 0.078 Uiso 1 1 calc GR . . . .
H8'C H 0.046797 0.311000 0.959055 0.078 Uiso 1 1 calc GR . . . .
H1B H 0.298(2) 0.828(2) 0.4100(16) 0.054(8) Uiso 1 1 d D . . . .
H4'A H 0.658(2) 0.551(2) 0.8389(15) 0.048(8) Uiso 1 1 d D . . . .
H4'B H 0.839(2) 0.505(2) 0.8373(16) 0.048(8) Uiso 1 1 d D . . . .
H4A H 0.542(3) 0.861(3) 0.4752(16) 0.069(9) Uiso 1 1 d D . . . .
H4B H 0.365(2) 0.9230(19) 0.5156(16) 0.043(7) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3' C7' 1.261(2) . ?
O2' C1' 1.400(3) . ?
O2' C9' 1.364(3) . ?
O2 C1 1.408(3) . ?
O2 C9 1.362(3) . ?
O4 C7 1.255(3) . ?
O3 C7 1.250(3) . ?
O4' C7' 1.246(2) . ?
O1 C9 1.196(3) . ?
N3 C11 1.346(3) . ?
N3 C10 1.344(3) . ?
O1' C9' 1.197(3) . ?
N3' C11' 1.348(3) . ?
N3' C10' 1.342(3) . ?
N4 C11 1.340(3) . ?
N4 H4A 0.951(18) . ?
N4 H4B 0.935(18) . ?
N5' C11' 1.330(3) . ?
N5' C13' 1.461(3) . ?
N5' C12' 1.461(3) . ?
N5 C11 1.332(3) . ?
N5 C12 1.459(3) . ?
N5 C13 1.468(3) . ?
O5 H5A 0.8601 . ?
O5 H5B 0.8601 . ?
N4' C11' 1.346(3) . ?
N4' H4'A 0.914(15) . ?
N4' H4'B 0.892(15) . ?
N1' H1'A 0.8700 . ?
N1' H1'B 0.8700 . ?
N1' C10' 1.326(3) . ?
N2' H2'A 0.8700 . ?
N2' H2'B 0.8700 . ?
N2' C10' 1.336(3) . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?
N2 C10 1.328(3) . ?
N1 H1A 0.83(3) . ?
N1 C10 1.333(3) . ?
N1 H1B 0.924(19) . ?
C7 C6 1.512(3) . ?
C6' C7' 1.507(3) . ?
C6' C1' 1.394(3) . ?
C6' C5' 1.392(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.388(3) . ?
C6 C5 1.394(3) . ?
C9 C8 1.493(3) . ?
C1' C2' 1.386(3) . ?
C9' C8' 1.492(3) . ?
C13' H13D 0.9700 . ?
C13' H13E 0.9700 . ?
C13' H13F 0.9700 . ?
C5 H5 0.9400 . ?
C5 C4 1.383(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C5' H5' 0.9400 . ?
C5' C4' 1.394(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.372(3) . ?
C4 H4 0.9400 . ?
C4 C3 1.376(4) . ?
C12' H12D 0.9700 . ?
C12' H12E 0.9700 . ?
C12' H12F 0.9700 . ?
C4' H4' 0.9400 . ?
C4' C3' 1.369(4) . ?
C2' H2' 0.9400 . ?
C2' C3' 1.374(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C3 H3 0.9400 . ?
C3' H3' 0.9400 . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' H8'C 0.9700 . ?

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
C9' O2' C1' 117.83(17) . . ?
C9 O2 C1 118.10(18) . . ?
C10 N3 C11 119.38(18) . . ?
C10' N3' C11' 122.05(18) . . ?
C11 N4 H4A 121.9(18) . . ?
C11 N4 H4B 120.6(15) . . ?
H4A N4 H4B 114(2) . . ?
C11' N5' C13' 121.44(18) . . ?
C11' N5' C12' 122.37(18) . . ?
C13' N5' C12' 116.20(18) . . ?
C11 N5 C12 122.09(19) . . ?
C11 N5 C13 121.76(19) . . ?
C12 N5 C13 115.65(19) . . ?
H5A O5 H5B 104.5 . . ?
C11' N4' H4'A 126.2(16) . . ?
C11' N4' H4'B 117.3(17) . . ?
H4'A N4' H4'B 114(2) . . ?
H1'A N1' H1'B 120.0 . . ?
C10' N1' H1'A 120.0 . . ?
C10' N1' H1'B 120.0 . . ?
H2'A N2' H2'B 120.0 . . ?
C10' N2' H2'A 120.0 . . ?
C10' N2' H2'B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H1A N1 H1B 118(2) . . ?
C10 N1 H1A 118.5(19) . . ?
C10 N1 H1B 122.5(17) . . ?
N4 C11 N3 122.4(2) . . ?
N5 C11 N3 118.38(19) . . ?
N5 C11 N4 118.88(19) . . ?
N5' C11' N3' 118.63(19) . . ?
N5' C11' N4' 118.55(19) . . ?
N4' C11' N3' 122.5(2) . . ?
O4 C7 C6 116.54(19) . . ?
O3 C7 O4 125.3(2) . . ?
O3 C7 C6 118.2(2) . . ?
N1' C10' N3' 124.87(19) . . ?
N1' C10' N2' 117.34(19) . . ?
N2' C10' N3' 117.74(19) . . ?
C1' C6' C7' 122.09(19) . . ?
C5' C6' C7' 121.0(2) . . ?
C5' C6' C1' 116.9(2) . . ?
C6 C1 O2 122.03(19) . . ?
C2 C1 O2 115.9(2) . . ?
C2 C1 C6 122.0(2) . . ?
C1 C6 C7 123.86(19) . . ?
C1 C6 C5 117.08(19) . . ?
C5 C6 C7 119.0(2) . . ?
N2 C10 N3 118.03(19) . . ?
N2 C10 N1 117.0(2) . . ?
N1 C10 N3 124.9(2) . . ?
O3' C7' C6' 115.95(18) . . ?
O4' C7' O3' 125.1(2) . . ?
O4' C7' C6' 118.93(19) . . ?
O2 C9 C8 110.4(2) . . ?
O1 C9 O2 122.9(2) . . ?
O1 C9 C8 126.7(2) . . ?
C6' C1' O2' 121.1(2) . . ?
C2' C1' O2' 116.4(2) . . ?
C2' C1' C6' 122.4(2) . . ?
O2' C9' C8' 110.3(2) . . ?
O1' C9' O2' 123.1(2) . . ?
O1' C9' C8' 126.5(2) . . ?
N5' C13' H13D 109.5 . . ?
N5' C13' H13E 109.5 . . ?
N5' C13' H13F 109.5 . . ?
H13D C13' H13E 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6' C5' H5' 119.5 . . ?
C6' C5' C4' 121.0(2) . . ?
C4' C5' H5' 119.5 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
N5' C12' H12D 109.5 . . ?
N5' C12' H12E 109.5 . . ?
N5' C12' H12F 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C5' C4' H4' 119.9 . . ?
C3' C4' C5' 120.2(2) . . ?
C3' C4' H4' 119.9 . . ?
C1' C2' H2' 120.5 . . ?
C3' C2' C1' 119.0(3) . . ?
C3' C2' H2' 120.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4' C3' C2' 120.5(3) . . ?
C4' C3' H3' 119.7 . . ?
C2' C3' H3' 119.7 . . ?
C9' C8' H8'A 109.5 . . ?
C9' C8' H8'B 109.5 . . ?
C9' C8' H8'C 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?

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
_geom_hbond_publ_flag
O5 H5B O3 0.86 1.95 2.777(2) 159.8 . yes
N1' H1'A O3' 0.87 1.90 2.760(2) 168.9 1_655 yes
N1' H1'B O3' 0.87 2.07 2.855(2) 150.2 2_667 yes
N2 H2A O4 0.87 2.00 2.843(2) 162.9 1_455 yes
N4' H4'A O4' 0.914(15) 1.961(16) 2.862(2) 169(2) . yes
N4 H4A O3 0.951(18) 1.91(2) 2.841(2) 165(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2' C1' C2' C3' -177.2(2) . . . . ?
O2 C1 C6 C7 7.0(3) . . . . ?
O2 C1 C6 C5 -174.9(2) . . . . ?
O2 C1 C2 C3 173.9(2) . . . . ?
O4 C7 C6 C1 138.2(2) . . . . ?
O4 C7 C6 C5 -39.9(3) . . . . ?
O3 C7 C6 C1 -42.9(3) . . . . ?
O3 C7 C6 C5 139.0(2) . . . . ?
C11 N3 C10 N2 -159.3(2) . . . . ?
C11 N3 C10 N1 23.8(3) . . . . ?
C11' N3' C10' N1' -25.3(3) . . . . ?
C11' N3' C10' N2' 157.4(2) . . . . ?
C7 C6 C5 C4 179.8(2) . . . . ?
C10' N3' C11' N5' 152.2(2) . . . . ?
C10' N3' C11' N4' -34.4(3) . . . . ?
C6' C1' C2' C3' -0.4(4) . . . . ?
C6' C5' C4' C3' 0.8(4) . . . . ?
C1 O2 C9 O1 -5.8(3) . . . . ?
C1 O2 C9 C8 173.94(19) . . . . ?
C1 C6 C5 C4 1.6(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C6 C1 C2 C3 -2.7(4) . . . . ?
C6 C5 C4 C3 -3.4(4) . . . . ?
C10 N3 C11 N4 41.8(3) . . . . ?
C10 N3 C11 N5 -144.5(2) . . . . ?
C7' C6' C1' O2' 1.6(3) . . . . ?
C7' C6' C1' C2' -175.1(2) . . . . ?
C7' C6' C5' C4' 175.0(2) . . . . ?
C9 O2 C1 C6 -63.6(3) . . . . ?
C9 O2 C1 C2 119.8(2) . . . . ?
C1' O2' C9' O1' 10.2(3) . . . . ?
C1' O2' C9' C8' -171.2(2) . . . . ?
C1' C6' C7' O3' 41.3(3) . . . . ?
C1' C6' C7' O4' -139.6(2) . . . . ?
C1' C6' C5' C4' -2.1(3) . . . . ?
C1' C2' C3' C4' -1.1(4) . . . . ?
C9' O2' C1' C6' 59.2(3) . . . . ?
C9' O2' C1' C2' -123.9(2) . . . . ?
C13' N5' C11' N3' 171.1(2) . . . . ?
C13' N5' C11' N4' -2.6(3) . . . . ?
C5 C4 C3 C2 2.2(4) . . . . ?
C12 N5 C11 N3 -161.9(2) . . . . ?
C12 N5 C11 N4 12.0(3) . . . . ?
C5' C6' C7' O3' -135.7(2) . . . . ?
C5' C6' C7' O4' 43.5(3) . . . . ?
C5' C6' C1' O2' 178.66(19) . . . . ?
C5' C6' C1' C2' 2.0(3) . . . . ?
C5' C4' C3' C2' 0.9(4) . . . . ?
C2 C1 C6 C7 -176.7(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C12' N5' C11' N3' -9.2(3) . . . . ?
C12' N5' C11' N4' 177.1(2) . . . . ?
C13 N5 C11 N3 9.6(3) . . . . ?
C13 N5 C11 N4 -176.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
