# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1119_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1947615'
loop_
_audit_author_name
_audit_author_address
'Chengming Bian'
;NUC
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-26
_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         'C3 H N11 O6, 2(C H7 N4), 0.72(H2 O1)'
_chemical_formula_sum            'C5 H16.44 N19 O6.72'
_chemical_formula_weight         450.36
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3254(7)
_cell_length_b                   12.5221(13)
_cell_length_c                   19.3440(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.786(4)
_cell_angle_gamma                90
_cell_volume                     1743.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5633
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.4058.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             933
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23305
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.691
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2525
_reflns_number_total             3552
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.016
_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)+(0.0560P)²+1.5139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C5)
3. Others
 Sof(H17A)=Sof(N20)=Sof(H20A)=Sof(H20B)=Sof(N21)=Sof(H21A)=Sof(H21B)=Sof(C6)=1-
 FVAR(1)
 Sof(O7)=Sof(H7A)=Sof(H7B)=Sof(N19)=Sof(H19A)=Sof(H19B)=Sof(H17)=Sof(N18)=
 Sof(H18A)=Sof(H18B)=Sof(C5)=FVAR(1)
4.a Free rotating group:
 O7(H7A,H7B)
4.b Rotating group:
 N15(H15A,H15B), N16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N14(H14), N17(H17), N17(H17A)
4.d X=CH2 refined with riding coordinates:
 N12(H12A,H12B), N13(H13A,H13B), N19(H19A,H19B), N18(H18A,H18B), N20(H20A,
 H20B), N21(H21A,H21B)
;
_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 0.5547(3) 0.29597(15) 0.45730(9) 0.0436(5) Uani 1 1 d . . . . .
O6 O 0.1025(3) 0.19694(15) 0.14437(9) 0.0444(5) Uani 1 1 d . . . . .
N3 N 0.2414(3) 0.03225(16) 0.40370(10) 0.0352(5) Uani 1 1 d . . . . .
O4 O 0.6001(3) 0.40158(15) 0.37238(10) 0.0479(5) Uani 1 1 d . . . . .
N9 N 0.5323(3) 0.31676(18) 0.39324(11) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.0309(3) -0.21369(15) 0.48846(10) 0.0508(5) Uani 1 1 d . . . . .
N4 N 0.3444(3) 0.12446(16) 0.42430(11) 0.0366(5) Uani 1 1 d . . . . .
N6 N 0.1923(3) -0.05893(17) 0.50468(11) 0.0378(5) Uani 1 1 d . . . . .
N7 N 0.1162(3) -0.14463(18) 0.52890(12) 0.0414(5) Uani 1 1 d . . . . .
N11 N 0.1301(3) 0.17578(18) 0.21028(11) 0.0412(5) Uani 1 1 d . . . . .
N8 N 0.4409(3) 0.25578(18) 0.34308(11) 0.0415(5) Uani 1 1 d . . . . .
N10 N 0.2765(3) 0.11635(18) 0.23354(11) 0.0424(5) Uani 1 1 d . . . . .
O5 O 0.0238(3) 0.21043(17) 0.24838(11) 0.0560(6) Uani 1 1 d . . . . .
O1 O 0.1341(3) -0.15239(16) 0.59414(10) 0.0504(5) Uani 1 1 d . . . . .
N1 N 0.0864(3) -0.11023(17) 0.37898(11) 0.0392(5) Uani 1 1 d . . . . .
H1 H 0.026457 -0.169948 0.383584 0.047 Uiso 1 1 calc R . . . .
N5 N 0.2807(3) 0.10017(18) 0.30608(11) 0.0420(5) Uani 1 1 d . . . . .
N2 N 0.1034(3) -0.06834(18) 0.31379(11) 0.0445(5) Uani 1 1 d . . . . .
C1 C 0.1688(3) -0.0520(2) 0.43400(13) 0.0349(5) Uani 1 1 d . . . . .
C2 C 0.1997(4) 0.0177(2) 0.33366(13) 0.0396(6) Uani 1 1 d . . . . .
C3 C 0.3620(3) 0.1645(2) 0.36246(13) 0.0380(6) Uani 1 1 d . . . . .
N14 N 0.0828(3) 0.38249(18) 0.42063(12) 0.0439(5) Uani 1 1 d . . . . .
H14 H 0.051955 0.320165 0.436062 0.053 Uiso 1 1 calc R . . . .
N12 N 0.2386(3) 0.54201(17) 0.44084(11) 0.0438(5) Uani 1 1 d . . . . .
H12A H 0.306027 0.586863 0.470059 0.053 Uiso 1 1 calc R . . . .
H12B H 0.208544 0.557675 0.395796 0.053 Uiso 1 1 calc R . . . .
N13 N 0.2281(3) 0.42813(18) 0.53233(11) 0.0445(5) Uani 1 1 d . . . . .
H13A H 0.295545 0.473223 0.561351 0.053 Uiso 1 1 calc R . . . .
H13B H 0.191005 0.367708 0.548388 0.053 Uiso 1 1 calc R . . . .
C4 C 0.1825(3) 0.4512(2) 0.46460(13) 0.0372(6) Uani 1 1 d . . . . .
N15 N 0.0267(3) 0.4097(2) 0.34940(12) 0.0491(6) Uani 1 1 d . . . . .
H15A H 0.044973 0.354936 0.322860 0.059 Uiso 1 1 d GR . . . .
H15B H -0.092335 0.426348 0.341220 0.059 Uiso 1 1 d GR . . . .
O7 O 0.3146(4) 0.4926(2) 0.27378(13) 0.0469(8) Uani 0.722(4) 1 d . . P A 1
H7A H 0.209880 0.473666 0.285170 0.070 Uiso 0.722(4) 1 d G . P A 1
H7B H 0.406570 0.468336 0.304933 0.070 Uiso 0.722(4) 1 d G . P A 1
N19 N 0.4697(5) 0.3118(3) 0.07228(17) 0.0424(8) Uani 0.722(4) 1 d . . P A 1
H19A H 0.425414 0.345108 0.032612 0.051 Uiso 0.722(4) 1 calc R . P A 1
H19B H 0.531303 0.251626 0.071659 0.051 Uiso 0.722(4) 1 calc R . P A 1
N17 N 0.5177(3) 0.30432(19) 0.19478(12) 0.0463(6) Uani 1 1 d . . . . .
H17 H 0.506336 0.328484 0.236484 0.056 Uiso 0.722(4) 1 calc R . P A 1
H17A H 0.521258 0.312811 0.240172 0.056 Uiso 0.278(4) 1 calc R . P A 2
N16 N 0.6131(4) 0.2124(2) 0.18363(14) 0.0585(7) Uani 1 1 d . . . . .
H16A H 0.555551 0.156372 0.196739 0.070 Uiso 1 1 d GR . . . .
H16B H 0.729359 0.218463 0.205406 0.070 Uiso 1 1 d GR . . . .
N18 N 0.3511(5) 0.4433(3) 0.13501(18) 0.0456(9) Uani 0.722(4) 1 d . . P A 1
H18A H 0.305996 0.477434 0.095771 0.055 Uiso 0.722(4) 1 calc R . P A 1
H18B H 0.334951 0.469250 0.175698 0.055 Uiso 0.722(4) 1 calc R . P A 1
C5 C 0.4438(6) 0.3524(4) 0.1328(3) 0.0390(10) Uani 0.722(4) 1 d . . P A 1
N20 N 0.3417(13) 0.4593(8) 0.1927(6) 0.062(3) Uani 0.278(4) 1 d . . P A 2
H20A H 0.283916 0.512550 0.168136 0.075 Uiso 0.278(4) 1 calc R . P A 2
H20B H 0.345641 0.456076 0.238426 0.075 Uiso 0.278(4) 1 calc R . P A 2
N21 N 0.4255(14) 0.3806(11) 0.0945(7) 0.056(3) Uani 0.278(4) 1 d . . P A 2
H21A H 0.485784 0.329750 0.076834 0.068 Uiso 0.278(4) 1 calc R . P A 2
H21B H 0.366197 0.430187 0.066826 0.068 Uiso 0.278(4) 1 calc R . P A 2
C6 C 0.4242(17) 0.3825(11) 0.1603(7) 0.0390(10) Uani 0.278(4) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N9 1.247(3) . ?
O6 N11 1.281(3) . ?
N3 N4 1.396(3) . ?
N3 C1 1.362(3) . ?
N3 C2 1.344(3) . ?
O4 N9 1.270(3) . ?
N9 N8 1.315(3) . ?
O2 N7 1.252(3) . ?
N4 C3 1.326(3) . ?
N6 N7 1.334(3) . ?
N6 C1 1.349(3) . ?
N7 O1 1.248(3) . ?
N11 N10 1.314(3) . ?
N11 O5 1.246(3) . ?
N8 C3 1.364(3) . ?
N10 N5 1.412(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.393(3) . ?
N1 C1 1.338(3) . ?
N5 C2 1.350(3) . ?
N5 C3 1.397(3) . ?
N2 C2 1.306(3) . ?
N14 H14 0.8800 . ?
N14 C4 1.328(3) . ?
N14 N15 1.404(3) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C4 1.321(3) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N13 C4 1.322(3) . ?
N15 H15A 0.8822 . ?
N15 H15B 0.8816 . ?
O7 H7A 0.8699 . ?
O7 H7B 0.8704 . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
N19 C5 1.322(6) . ?
N17 H17 0.8800 . ?
N17 H17A 0.8800 . ?
N17 N16 1.385(3) . ?
N17 C5 1.360(6) . ?
N17 C6 1.304(15) . ?
N16 H16A 0.8799 . ?
N16 H16B 0.8797 . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?
N18 C5 1.330(7) . ?
N20 H20A 0.8800 . ?
N20 H20B 0.8800 . ?
N20 C6 1.351(16) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?
N21 C6 1.274(16) . ?

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 N3 N4 138.7(2) . . ?
C2 N3 N4 114.1(2) . . ?
C2 N3 C1 107.2(2) . . ?
O3 N9 O4 120.3(2) . . ?
O3 N9 N8 124.5(2) . . ?
O4 N9 N8 115.3(2) . . ?
C3 N4 N3 101.21(19) . . ?
N7 N6 C1 115.2(2) . . ?
O2 N7 N6 121.9(2) . . ?
O1 N7 O2 121.6(2) . . ?
O1 N7 N6 116.5(2) . . ?
O6 N11 N10 115.1(2) . . ?
O5 N11 O6 121.1(2) . . ?
O5 N11 N10 123.7(2) . . ?
N9 N8 C3 117.8(2) . . ?
N11 N10 N5 106.6(2) . . ?
N2 N1 H1 122.9 . . ?
C1 N1 H1 122.9 . . ?
C1 N1 N2 114.3(2) . . ?
C2 N5 N10 125.0(2) . . ?
C2 N5 C3 106.7(2) . . ?
C3 N5 N10 128.3(2) . . ?
C2 N2 N1 100.3(2) . . ?
N6 C1 N3 120.0(2) . . ?
N1 C1 N3 103.6(2) . . ?
N1 C1 N6 136.4(2) . . ?
N3 C2 N5 105.1(2) . . ?
N2 C2 N3 114.6(2) . . ?
N2 C2 N5 140.2(2) . . ?
N4 C3 N8 133.1(2) . . ?
N4 C3 N5 112.8(2) . . ?
N8 C3 N5 114.2(2) . . ?
C4 N14 H14 120.1 . . ?
C4 N14 N15 119.7(2) . . ?
N15 N14 H14 120.1 . . ?
H12A N12 H12B 120.0 . . ?
C4 N12 H12A 120.0 . . ?
C4 N12 H12B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C4 N13 H13A 120.0 . . ?
C4 N13 H13B 120.0 . . ?
N12 C4 N14 120.3(2) . . ?
N12 C4 N13 119.7(2) . . ?
N13 C4 N14 120.0(2) . . ?
N14 N15 H15A 109.5 . . ?
N14 N15 H15B 109.3 . . ?
H15A N15 H15B 109.4 . . ?
H7A O7 H7B 109.5 . . ?
H19A N19 H19B 120.0 . . ?
C5 N19 H19A 120.0 . . ?
C5 N19 H19B 120.0 . . ?
N16 N17 H17 124.5 . . ?
N16 N17 H17A 109.5 . . ?
C5 N17 H17 124.5 . . ?
C5 N17 N16 111.1(3) . . ?
C6 N17 H17A 109.5 . . ?
C6 N17 N16 140.9(6) . . ?
N17 N16 H16A 109.5 . . ?
N17 N16 H16B 109.0 . . ?
H16A N16 H16B 113.8 . . ?
H18A N18 H18B 120.0 . . ?
C5 N18 H18A 120.0 . . ?
C5 N18 H18B 120.0 . . ?
N19 C5 N17 120.8(4) . . ?
N19 C5 N18 121.0(5) . . ?
N18 C5 N17 118.1(5) . . ?
H20A N20 H20B 120.0 . . ?
C6 N20 H20A 120.0 . . ?
C6 N20 H20B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
C6 N21 H21A 120.0 . . ?
C6 N21 H21B 120.0 . . ?
N17 C6 N20 122.3(11) . . ?
N21 C6 N17 113.3(12) . . ?
N21 C6 N20 124.3(13) . . ?

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1947617'
loop_
_audit_author_name
_audit_author_address
'Chengming Bian'
;NUC
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N11 O6, H2 O, 2(C H6 N3)'
_chemical_formula_sum            'C5 H15 N17 O7'
_chemical_formula_weight         425.34
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     C4A-A2G-ACE3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7723(3)
_cell_length_b                   13.1291(5)
_cell_length_c                   18.8628(8)
_cell_angle_alpha                85.471(3)
_cell_angle_beta                 80.793(4)
_cell_angle_gamma                82.300(3)
_cell_volume                     1637.80(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2443
_cell_measurement_temperature    189.7(10)
_cell_measurement_theta_max      72.8960
_cell_measurement_theta_min      4.7450
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    1.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9467
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.403
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      189.7(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  21.00   1.00    1.00    --  -40.08  57.00 120.00   88
  2  ω   -115.00  -8.00   1.00    1.00    --  -40.08 -77.00 -30.00  107
  3  ω    -67.00  33.00   1.00    1.00    --  -40.08  57.00-120.00  100
  4  ω    107.00 171.00   1.00    1.00    --  105.48 125.00 -60.00   64
  5  ω     55.00 178.00   1.00    1.00    --  105.48  15.00   0.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1027915000
_diffrn_orient_matrix_UB_12      0.0074388000
_diffrn_orient_matrix_UB_13      0.0662738000
_diffrn_orient_matrix_UB_21      -0.1437086000
_diffrn_orient_matrix_UB_22      -0.0705642000
_diffrn_orient_matrix_UB_23      0.0447444000
_diffrn_orient_matrix_UB_31      0.1505264000
_diffrn_orient_matrix_UB_32      -0.0950393000
_diffrn_orient_matrix_UB_33      -0.0218868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5006
_reflns_number_total             5733
_reflns_odcompleteness_completeness 59.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         5733
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.4072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2WA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2W) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2W) = Uanis(O2WA)
3. Others
 Sof(O2WA)=Sof(H2WC)=Sof(H2WD)=1-FVAR(1)
 Sof(O2W)=Sof(H2WA)=Sof(H2WB)=FVAR(1)
4.a Riding coordinates:
 O2W(H2WA,H2WB), O2WA(H2WC,H2WD)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N13(H13)
4.c X=CH2 refined with riding coordinates:
 N26(H26A,H26B), N27(H27A,H27B), N28(H28B,H28A), N29(H29A,H29B), N30(H30A,
 H30B), N31(H31B,H31A), N32(H32A,H32B), N33(H33A,H33B), N34(H34A,H34B),
 N23(H23B,H23A), N24(H24A,H24B), N25(H25B,H25A)
;
_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
O1 O 0.08933(19) 1.69278(9) 0.97610(6) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.0790(2) 1.64491(9) 1.08957(6) 0.0295(3) Uani 1 1 d . . . . .
O3 O 0.81688(18) 1.31231(9) 0.76950(7) 0.0290(3) Uani 1 1 d . . . . .
O5 O 0.6035(2) 1.15359(9) 1.00275(6) 0.0312(3) Uani 1 1 d . . . . .
O6 O 0.68569(19) 1.02402(9) 0.93444(6) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.1288(2) 1.62630(10) 1.02484(7) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.2242(2) 1.53300(10) 1.01075(7) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.2384(2) 1.56742(10) 0.87752(7) 0.0205(3) Uani 1 1 d . . . . .
H3 H 0.1851 1.6306 0.8751 0.025 Uiso 1 1 calc R . . . .
N4 N 0.3042(2) 1.51022(10) 0.81690(7) 0.0212(3) Uani 1 1 d . . . . .
N5 N 0.3527(2) 1.41984(10) 0.91899(7) 0.0186(3) Uani 1 1 d . . . . .
N6 N 0.4241(2) 1.32535(10) 0.95018(7) 0.0200(3) Uani 1 1 d . . . . .
N7 N 0.5675(2) 1.17066(10) 0.88505(7) 0.0219(3) Uani 1 1 d . . . . .
N8 N 0.6178(2) 1.11692(10) 0.94341(7) 0.0216(3) Uani 1 1 d . . . . .
N9 N 0.4927(2) 1.29519(10) 0.75769(7) 0.0215(3) Uani 1 1 d . . . . .
N10 N 0.6884(2) 1.29532(10) 0.73270(7) 0.0217(3) Uani 1 1 d . . . . .
N20 N 0.4553(2) 1.32636(10) 0.82855(7) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.2662(2) 1.51462(12) 0.93992(8) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.3706(2) 1.42212(12) 0.84674(8) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.4863(2) 1.27022(12) 0.89307(8) 0.0194(3) Uani 1 1 d . . . . .
O4 O 0.73634(19) 1.27751(9) 0.66732(6) 0.0296(3) Uani 1 1 d . . . A 1
O1W O 0.6143(2) 1.10820(12) 0.59924(7) 0.0357(3) Uani 1 1 d . . . . .
H1WA H 0.639(4) 1.171(3) 0.6065(16) 0.074(9) Uiso 1 1 d . . . . .
H1WB H 0.620(4) 1.105(2) 0.5551(16) 0.058(8) Uiso 1 1 d . . . . .
O8 O 0.00079(19) 1.23323(9) 0.41259(6) 0.0264(3) Uani 1 1 d . . . . .
O9 O 0.5209(2) 0.73849(10) 0.49843(6) 0.0354(3) Uani 1 1 d . . . . .
O10 O 0.6637(2) 0.62308(9) 0.56876(6) 0.0301(3) Uani 1 1 d . . . . .
O11 O 0.11664(18) 0.76251(9) 0.73405(6) 0.0275(3) Uani 1 1 d . . . . .
O12 O 0.2363(2) 0.77245(9) 0.83399(6) 0.0303(3) Uani 1 1 d . . . . .
N11 N 0.0225(2) 1.20961(10) 0.47654(7) 0.0203(3) Uani 1 1 d . . . . .
N12 N 0.1239(2) 1.11759(10) 0.48979(7) 0.0205(3) Uani 1 1 d . . . . .
N13 N 0.0814(2) 1.14092(10) 0.62177(7) 0.0203(3) Uani 1 1 d . . . . .
H13 H 0.0189 1.2024 0.6236 0.024 Uiso 1 1 calc R . . . .
N14 N 0.1284(2) 1.08149(10) 0.68284(7) 0.0207(3) Uani 1 1 d . . . . .
N15 N 0.2370(2) 1.00157(10) 0.58121(7) 0.0178(3) Uani 1 1 d . . . . .
N16 N 0.3443(2) 0.91339(10) 0.55064(7) 0.0194(3) Uani 1 1 d . . . . .
N17 N 0.4967(2) 0.76150(10) 0.61709(7) 0.0216(3) Uani 1 1 d . . . . .
N18 N 0.5593(2) 0.70837(10) 0.55903(7) 0.0218(3) Uani 1 1 d . . . . .
N19 N 0.3136(2) 0.90372(10) 0.67237(7) 0.0195(3) Uani 1 1 d . . . . .
N21 N 0.3455(2) 0.87207(10) 0.74288(7) 0.0202(3) Uani 1 1 d . . . . .
N22 N 0.2269(2) 0.80024(10) 0.76909(7) 0.0211(3) Uani 1 1 d . . . . .
N26 N 0.7591(2) 0.52267(12) 0.70171(9) 0.0353(4) Uani 1 1 d . . . . .
H26A H 0.7261 0.5495 0.6615 0.042 Uiso 1 1 calc R . . . .
H26B H 0.8072 0.4588 0.7053 0.042 Uiso 1 1 calc R . . . .
N27 N 0.6621(2) 0.67776(12) 0.75204(9) 0.0323(4) Uani 1 1 d . . . . .
H27A H 0.6453 0.7150 0.7886 0.039 Uiso 1 1 calc R . . . .
H27B H 0.6309 0.7044 0.7116 0.039 Uiso 1 1 calc R . . . .
N28 N 0.7838(2) 0.53912(12) 0.82037(9) 0.0339(4) Uani 1 1 d . . . . .
H28B H 0.7669 0.5765 0.8568 0.041 Uiso 1 1 calc R . . . .
H28A H 0.8320 0.4753 0.8244 0.041 Uiso 1 1 calc R . . . .
N29 N -0.2102(2) 0.91638(12) 0.80089(8) 0.0331(4) Uani 1 1 d . . . . .
H29A H -0.2451 0.9417 0.8424 0.040 Uiso 1 1 calc R . . . .
H29B H -0.1372 0.8577 0.7970 0.040 Uiso 1 1 calc R . . . .
N30 N -0.2182(2) 0.92984(11) 0.67854(8) 0.0280(3) Uani 1 1 d . . . . .
H30A H -0.2582 0.9638 0.6415 0.034 Uiso 1 1 calc R . . . .
H30B H -0.1453 0.8712 0.6739 0.034 Uiso 1 1 calc R . . . .
N31 N -0.3813(2) 1.05805(11) 0.74994(8) 0.0278(3) Uani 1 1 d . . . . .
H31B H -0.4211 1.0919 0.7128 0.033 Uiso 1 1 calc R . . . .
H31A H -0.4144 1.0829 0.7916 0.033 Uiso 1 1 calc R . . . .
N32 N 0.2419(2) 0.98971(11) 0.88064(7) 0.0266(3) Uani 1 1 d . . . . .
H32A H 0.2826 0.9494 0.9150 0.032 Uiso 1 1 calc R . . . .
H32B H 0.2633 0.9698 0.8374 0.032 Uiso 1 1 calc R . . . .
N33 N 0.0839(2) 1.14572(11) 0.84183(8) 0.0287(3) Uani 1 1 d . . . . .
H33A H 0.1053 1.1266 0.7984 0.034 Uiso 1 1 calc R . . . .
H33B H 0.0221 1.2058 0.8512 0.034 Uiso 1 1 calc R . . . .
N34 N 0.1147(2) 1.11206(11) 0.96122(7) 0.0271(3) Uani 1 1 d . . . . .
H34A H 0.1559 1.0712 0.9952 0.032 Uiso 1 1 calc R . . . .
H34B H 0.0528 1.1722 0.9706 0.032 Uiso 1 1 calc R . . . .
C4 C 0.3896(2) 0.85562(12) 0.60824(8) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.2230(2) 0.99787(12) 0.65348(8) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.1418(2) 1.09416(12) 0.55983(8) 0.0183(3) Uani 1 1 d . . . . .
C7 C -0.2691(3) 0.96791(13) 0.74290(9) 0.0240(4) Uani 1 1 d . . . . .
C8 C 0.1465(2) 1.08245(12) 0.89431(9) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.7359(3) 0.57982(14) 0.75810(10) 0.0272(4) Uani 1 1 d . . . . .
O7 O -0.04848(19) 1.26996(9) 0.52502(6) 0.0285(3) Uani 1 1 d . . . B 1
N23 N 0.2230(2) 0.56811(11) 0.65796(8) 0.0304(3) Uani 1 1 d . . . . .
H23B H 0.1729 0.6305 0.6484 0.036 Uiso 1 1 calc R . . . .
H23A H 0.2517 0.5496 0.7003 0.036 Uiso 1 1 calc R . . . .
N24 N 0.2121(3) 0.52877(12) 0.54254(8) 0.0366(4) Uani 1 1 d . . . . .
H24A H 0.2321 0.4846 0.5100 0.044 Uiso 1 1 calc R . . . .
H24B H 0.1635 0.5913 0.5327 0.044 Uiso 1 1 calc R . . . .
N25 N 0.3304(3) 0.40428(12) 0.62185(8) 0.0393(4) Uani 1 1 d . . . . .
H25B H 0.3499 0.3607 0.5890 0.047 Uiso 1 1 calc R . . . .
H25A H 0.3595 0.3852 0.6640 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2559(3) 0.50064(13) 0.60759(9) 0.0254(4) Uani 1 1 d . . . . .
O2W O -0.2663(4) 0.72730(14) 0.89968(9) 0.0414(5) Uani 0.821(4) 1 d . U P C 1
H2WA H -0.1823 0.7246 0.9364 0.062 Uiso 0.821(4) 1 d R . P C 1
H2WB H -0.4049 0.7302 0.9216 0.062 Uiso 0.821(4) 1 d R . P C 1
O2WA O -0.3879(18) 0.7143(7) 0.8935(4) 0.0414(5) Uani 0.179(4) 1 d . U P C 2
H2WC H -0.3122 0.6947 0.9324 0.062 Uiso 0.179(4) 1 d R . P C 2
H2WD H -0.5271 0.7330 0.9126 0.062 Uiso 0.179(4) 1 d R . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2521(17) . ?
O2 N1 1.2481(17) . ?
O3 N10 1.2483(19) . ?
O5 N8 1.2377(18) . ?
O6 N8 1.2591(17) . ?
N1 N2 1.3317(18) . ?
N2 C1 1.354(2) . ?
N3 H3 0.8600 . ?
N3 N4 1.3974(18) . ?
N3 C1 1.345(2) . ?
N4 C2 1.302(2) . ?
N5 N6 1.3908(18) . ?
N5 C1 1.362(2) . ?
N5 C2 1.347(2) . ?
N6 C3 1.326(2) . ?
N7 N8 1.3261(18) . ?
N7 C3 1.359(2) . ?
N9 N10 1.334(2) . ?
N9 N20 1.4029(17) . ?
N10 O4 1.2561(17) . ?
N20 C2 1.356(2) . ?
N20 C3 1.4028(19) . ?
O1W H1WA 0.89(3) . ?
O1W H1WB 0.83(3) . ?
O8 N11 1.2484(17) . ?
O9 N18 1.2356(18) . ?
O10 N18 1.2589(17) . ?
O11 N22 1.2446(18) . ?
O12 N22 1.2587(17) . ?
N11 N12 1.3337(18) . ?
N11 O7 1.2517(17) . ?
N12 C6 1.353(2) . ?
N13 H13 0.8600 . ?
N13 N14 1.3951(18) . ?
N13 C6 1.343(2) . ?
N14 C5 1.310(2) . ?
N15 N16 1.3952(18) . ?
N15 C5 1.3486(19) . ?
N15 C6 1.361(2) . ?
N16 C4 1.328(2) . ?
N17 N18 1.3261(18) . ?
N17 C4 1.359(2) . ?
N19 N21 1.4030(17) . ?
N19 C4 1.4005(19) . ?
N19 C5 1.352(2) . ?
N21 N22 1.3343(19) . ?
N26 H26A 0.8600 . ?
N26 H26B 0.8600 . ?
N26 C9 1.327(2) . ?
N27 H27A 0.8600 . ?
N27 H27B 0.8600 . ?
N27 C9 1.319(2) . ?
N28 H28B 0.8600 . ?
N28 H28A 0.8600 . ?
N28 C9 1.322(2) . ?
N29 H29A 0.8600 . ?
N29 H29B 0.8600 . ?
N29 C7 1.328(2) . ?
N30 H30A 0.8600 . ?
N30 H30B 0.8600 . ?
N30 C7 1.326(2) . ?
N31 H31B 0.8600 . ?
N31 H31A 0.8600 . ?
N31 C7 1.322(2) . ?
N32 H32A 0.8600 . ?
N32 H32B 0.8600 . ?
N32 C8 1.324(2) . ?
N33 H33A 0.8600 . ?
N33 H33B 0.8600 . ?
N33 C8 1.326(2) . ?
N34 H34A 0.8600 . ?
N34 H34B 0.8600 . ?
N34 C8 1.326(2) . ?
N23 H23B 0.8600 . ?
N23 H23A 0.8600 . ?
N23 C10 1.323(2) . ?
N24 H24A 0.8600 . ?
N24 H24B 0.8600 . ?
N24 C10 1.321(2) . ?
N25 H25B 0.8600 . ?
N25 H25A 0.8600 . ?
N25 C10 1.321(2) . ?
O2W H2WA 0.9600 . ?
O2W H2WB 0.9600 . ?
O2WA H2WC 0.9600 . ?
O2WA H2WD 0.9600 . ?

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 N1 N2 122.31(13) . . ?
O2 N1 O1 120.95(13) . . ?
O2 N1 N2 116.74(13) . . ?
N1 N2 C1 114.60(13) . . ?
N4 N3 H3 123.1 . . ?
C1 N3 H3 123.1 . . ?
C1 N3 N4 113.84(12) . . ?
C2 N4 N3 100.77(12) . . ?
C1 N5 N6 138.64(13) . . ?
C2 N5 N6 113.86(12) . . ?
C2 N5 C1 107.50(13) . . ?
C3 N6 N5 101.87(12) . . ?
N8 N7 C3 116.88(13) . . ?
O5 N8 O6 121.11(13) . . ?
O5 N8 N7 123.84(13) . . ?
O6 N8 N7 115.04(13) . . ?
N10 N9 N20 108.87(13) . . ?
O3 N10 N9 124.34(13) . . ?
O3 N10 O4 121.26(14) . . ?
O4 N10 N9 114.40(14) . . ?
C2 N20 N9 123.55(13) . . ?
C2 N20 C3 106.39(13) . . ?
C3 N20 N9 130.02(13) . . ?
N2 C1 N5 120.04(14) . . ?
N3 C1 N2 136.45(14) . . ?
N3 C1 N5 103.46(13) . . ?
N4 C2 N5 114.43(14) . . ?
N4 C2 N20 140.20(15) . . ?
N5 C2 N20 105.37(13) . . ?
N6 C3 N7 133.00(14) . . ?
N6 C3 N20 112.51(13) . . ?
N7 C3 N20 114.45(13) . . ?
H1WA O1W H1WB 107(3) . . ?
O8 N11 N12 116.47(13) . . ?
O8 N11 O7 120.96(13) . . ?
O7 N11 N12 122.57(13) . . ?
N11 N12 C6 114.72(13) . . ?
N14 N13 H13 122.8 . . ?
C6 N13 H13 122.8 . . ?
C6 N13 N14 114.39(12) . . ?
C5 N14 N13 100.49(12) . . ?
C5 N15 N16 113.30(12) . . ?
C5 N15 C6 107.79(13) . . ?
C6 N15 N16 138.89(13) . . ?
C4 N16 N15 102.03(12) . . ?
N18 N17 C4 117.44(13) . . ?
O9 N18 O10 120.54(13) . . ?
O9 N18 N17 123.71(13) . . ?
O10 N18 N17 115.75(13) . . ?
C4 N19 N21 129.18(12) . . ?
C5 N19 N21 123.65(13) . . ?
C5 N19 C4 106.53(12) . . ?
N22 N21 N19 109.49(12) . . ?
O11 N22 O12 121.80(14) . . ?
O11 N22 N21 124.62(13) . . ?
O12 N22 N21 113.59(14) . . ?
H26A N26 H26B 120.0 . . ?
C9 N26 H26A 120.0 . . ?
C9 N26 H26B 120.0 . . ?
H27A N27 H27B 120.0 . . ?
C9 N27 H27A 120.0 . . ?
C9 N27 H27B 120.0 . . ?
H28B N28 H28A 120.0 . . ?
C9 N28 H28B 120.0 . . ?
C9 N28 H28A 120.0 . . ?
H29A N29 H29B 120.0 . . ?
C7 N29 H29A 120.0 . . ?
C7 N29 H29B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
C7 N30 H30A 120.0 . . ?
C7 N30 H30B 120.0 . . ?
H31B N31 H31A 120.0 . . ?
C7 N31 H31B 120.0 . . ?
C7 N31 H31A 120.0 . . ?
H32A N32 H32B 120.0 . . ?
C8 N32 H32A 120.0 . . ?
C8 N32 H32B 120.0 . . ?
H33A N33 H33B 120.0 . . ?
C8 N33 H33A 120.0 . . ?
C8 N33 H33B 120.0 . . ?
H34A N34 H34B 120.0 . . ?
C8 N34 H34A 120.0 . . ?
C8 N34 H34B 120.0 . . ?
N16 C4 N17 133.17(14) . . ?
N16 C4 N19 112.35(13) . . ?
N17 C4 N19 114.46(13) . . ?
N14 C5 N15 114.08(14) . . ?
N14 C5 N19 140.22(15) . . ?
N15 C5 N19 105.68(13) . . ?
N12 C6 N15 120.91(14) . . ?
N13 C6 N12 135.86(14) . . ?
N13 C6 N15 103.21(13) . . ?
N30 C7 N29 120.95(16) . . ?
N31 C7 N29 119.18(15) . . ?
N31 C7 N30 119.87(15) . . ?
N32 C8 N33 120.67(15) . . ?
N32 C8 N34 119.30(15) . . ?
N34 C8 N33 120.03(15) . . ?
N27 C9 N26 119.57(16) . . ?
N27 C9 N28 119.86(18) . . ?
N28 C9 N26 120.57(17) . . ?
H23B N23 H23A 120.0 . . ?
C10 N23 H23B 120.0 . . ?
C10 N23 H23A 120.0 . . ?
H24A N24 H24B 120.0 . . ?
C10 N24 H24A 120.0 . . ?
C10 N24 H24B 120.0 . . ?
H25B N25 H25A 120.0 . . ?
C10 N25 H25B 120.0 . . ?
C10 N25 H25A 120.0 . . ?
N24 C10 N23 120.17(16) . . ?
N24 C10 N25 119.26(16) . . ?
N25 C10 N23 120.57(16) . . ?
H2WA O2W H2WB 109.5 . . ?
H2WC O2WA H2WD 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 C1 -2.9(2) . . . . ?
O2 N1 N2 C1 176.86(14) . . . . ?
N1 N2 C1 N3 0.9(3) . . . . ?
N1 N2 C1 N5 -176.05(14) . . . . ?
N3 N4 C2 N5 -0.18(18) . . . . ?
N3 N4 C2 N20 179.2(2) . . . . ?
N4 N3 C1 N2 -177.39(18) . . . . ?
N4 N3 C1 N5 -0.13(18) . . . . ?
N5 N6 C3 N7 -178.03(18) . . . . ?
N5 N6 C3 N20 -0.31(18) . . . . ?
N6 N5 C1 N2 -2.0(3) . . . . ?
N6 N5 C1 N3 -179.85(18) . . . . ?
N6 N5 C2 N4 -179.99(14) . . . . ?
N6 N5 C2 N20 0.41(19) . . . . ?
N8 N7 C3 N6 -8.6(3) . . . . ?
N8 N7 C3 N20 173.75(14) . . . . ?
N9 N20 C2 N4 -2.0(3) . . . . ?
N9 N20 C2 N5 177.47(14) . . . . ?
N9 N20 C3 N6 -177.29(15) . . . . ?
N9 N20 C3 N7 0.9(2) . . . . ?
N10 N9 N20 C2 102.30(17) . . . . ?
N10 N9 N20 C3 -80.2(2) . . . . ?
N20 N9 N10 O3 5.47(19) . . . . ?
N20 N9 N10 O4 -173.91(12) . . . . ?
C1 N3 N4 C2 0.19(18) . . . . ?
C1 N5 N6 C3 179.79(19) . . . . ?
C1 N5 C2 N4 0.1(2) . . . . ?
C1 N5 C2 N20 -179.49(13) . . . . ?
C2 N5 N6 C3 -0.07(18) . . . . ?
C2 N5 C1 N2 177.83(15) . . . . ?
C2 N5 C1 N3 0.02(18) . . . . ?
C2 N20 C3 N6 0.58(19) . . . . ?
C2 N20 C3 N7 178.75(14) . . . . ?
C3 N7 N8 O5 -3.5(2) . . . . ?
C3 N7 N8 O6 177.55(14) . . . . ?
C3 N20 C2 N4 -180.0(2) . . . . ?
C3 N20 C2 N5 -0.57(18) . . . . ?
O8 N11 N12 C6 -179.09(14) . . . . ?
N11 N12 C6 N13 0.3(3) . . . . ?
N11 N12 C6 N15 178.23(14) . . . . ?
N13 N14 C5 N15 0.04(18) . . . . ?
N13 N14 C5 N19 -178.8(2) . . . . ?
N14 N13 C6 N12 176.51(18) . . . . ?
N14 N13 C6 N15 -1.69(18) . . . . ?
N15 N16 C4 N17 -177.87(18) . . . . ?
N15 N16 C4 N19 0.59(17) . . . . ?
N16 N15 C5 N14 177.85(13) . . . . ?
N16 N15 C5 N19 -2.95(18) . . . . ?
N16 N15 C6 N12 4.5(3) . . . . ?
N16 N15 C6 N13 -176.91(17) . . . . ?
N18 N17 C4 N16 -6.7(3) . . . . ?
N18 N17 C4 N19 174.83(14) . . . . ?
N19 N21 N22 O11 4.74(19) . . . . ?
N19 N21 N22 O12 -175.53(12) . . . . ?
N21 N19 C4 N16 -173.37(15) . . . . ?
N21 N19 C4 N17 5.4(2) . . . . ?
N21 N19 C5 N14 -6.4(3) . . . . ?
N21 N19 C5 N15 174.70(14) . . . . ?
C4 N17 N18 O9 -2.1(2) . . . . ?
C4 N17 N18 O10 177.71(14) . . . . ?
C4 N19 N21 N22 -79.75(19) . . . . ?
C4 N19 C5 N14 -178.1(2) . . . . ?
C4 N19 C5 N15 3.07(17) . . . . ?
C5 N15 N16 C4 1.47(18) . . . . ?
C5 N15 C6 N12 -176.95(15) . . . . ?
C5 N15 C6 N13 1.59(17) . . . . ?
C5 N19 N21 N22 110.63(16) . . . . ?
C5 N19 C4 N16 -2.38(19) . . . . ?
C5 N19 C4 N17 176.38(14) . . . . ?
C6 N13 N14 C5 1.07(18) . . . . ?
C6 N15 N16 C4 179.92(19) . . . . ?
C6 N15 C5 N14 -1.1(2) . . . . ?
C6 N15 C5 N19 178.12(13) . . . . ?
O7 N11 N12 C6 0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.674
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_553
_database_code_depnum_ccdc_archive 'CCDC 1947616'
loop_
_audit_author_name
_audit_author_address
'Chengming Bian'
;NUC
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H N11 O6, 2(C H8 N5)'
_chemical_formula_sum            'C5 H17 N21 O6'
_chemical_formula_weight         467.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     C4A-A2G-ACE3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.6291(2)
_cell_length_b                   13.4799(3)
_cell_length_c                   17.4739(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.389(2)
_cell_angle_gamma                90
_cell_volume                     1777.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2813
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5270
_cell_measurement_theta_min      5.1140
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    1.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5900
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         4.159
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    1.00    --  -40.08  38.00  60.00   99
  2  ω    -91.00  -4.00   1.00    1.00    --  -40.08 125.00  60.00   87
  3  ω    106.00 144.00   1.00    1.00    --  105.48 125.00-120.00   38
  4  ω     35.00 117.00   1.00    1.00    --  105.48-125.00  30.00   82
  5  ω     60.00 178.00   1.00    1.00    --  105.48  15.00 -60.00  118
  6  ω     23.00 104.00   1.00    1.00    --  105.48 -94.00-180.00   81
  7  ω     32.00 115.00   1.00    1.00    --  105.48 -45.00-180.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142806000
_diffrn_orient_matrix_UB_12      0.0531813000
_diffrn_orient_matrix_UB_13      -0.0769215000
_diffrn_orient_matrix_UB_21      -0.0311166000
_diffrn_orient_matrix_UB_22      0.1004988000
_diffrn_orient_matrix_UB_23      0.0377776000
_diffrn_orient_matrix_UB_31      0.2011490000
_diffrn_orient_matrix_UB_32      0.0117914000
_diffrn_orient_matrix_UB_33      0.0244916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2646
_reflns_number_total             3125
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.067
_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)+(0.0550P)²+1.2413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Riding coordinates:
 N17(H17A,H17B), N21(H21A,H21B), N12(H12A,H12B), N16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N18(H18), N20(H20), N13(H13), N15(H15)
2.c X=CH2 refined with riding coordinates:
 N19(H19A,H19B), N14(H14A,H14B)
;
_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
O1 O 0.4159(2) 0.75553(11) 0.50939(8) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.2957(2) 0.86914(12) 0.42955(9) 0.0384(4) Uani 1 1 d . . . . .
O3 O 0.7085(2) 0.72889(13) 0.25972(9) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.5098(2) 0.74216(11) 0.15615(8) 0.0259(3) Uani 1 1 d . . . A 1
O5 O 0.9855(2) 0.31418(12) 0.49262(9) 0.0326(4) Uani 1 1 d . . . B 1
O6 O 0.9844(2) 0.35914(12) 0.61259(9) 0.0313(4) Uani 1 1 d . . . . .
N1 N 0.3761(2) 0.78784(13) 0.44285(10) 0.0236(4) Uani 1 1 d . . . . .
N2 N 0.4105(2) 0.74200(13) 0.37927(10) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.5640(2) 0.70474(13) 0.22198(9) 0.0205(4) Uani 1 1 d . . . . .
N4 N 0.4547(2) 0.63836(13) 0.24587(9) 0.0205(4) Uani 1 1 d . . . . .
N5 N 0.5266(2) 0.60795(12) 0.32044(10) 0.0202(4) Uani 1 1 d . . . . .
N6 N 0.7097(2) 0.45372(13) 0.31103(10) 0.0225(4) Uani 1 1 d . . . . .
N7 N 0.7961(2) 0.40799(13) 0.37822(10) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.8580 0.3547 0.3775 0.026 Uiso 1 1 calc R . . . .
N8 N 0.6699(2) 0.53336(12) 0.41856(9) 0.0192(4) Uani 1 1 d . . . . .
N9 N 0.5915(2) 0.61259(12) 0.45165(10) 0.0204(4) Uani 1 1 d . . . . .
N10 N 0.8260(2) 0.44525(12) 0.52094(10) 0.0211(4) Uani 1 1 d . . . . .
N11 N 0.9345(2) 0.37010(13) 0.54177(10) 0.0228(4) Uani 1 1 d . . . . .
N17 N 0.5865(3) 0.74753(16) 0.70950(12) 0.0358(5) Uani 1 1 d . . . . .
H17A H 0.6453 0.8019 0.7219 0.043 Uiso 1 1 d R . . . .
H17B H 0.4890 0.7465 0.7298 0.043 Uiso 1 1 d R . . . .
N18 N 0.6912(3) 0.66665(16) 0.74182(11) 0.0346(5) Uani 1 1 d . . . . .
H18 H 0.7216 0.6610 0.7910 0.042 Uiso 1 1 calc R . . . .
N19 N 0.6747(3) 0.60247(15) 0.62014(11) 0.0317(4) Uani 1 1 d . . . . .
H19A H 0.5986 0.6472 0.6030 0.038 Uiso 1 1 calc R . . . .
H19B H 0.7074 0.5591 0.5890 0.038 Uiso 1 1 calc R . . . .
N20 N 0.8533(3) 0.52590(17) 0.71879(12) 0.0390(5) Uani 1 1 d . . . . .
H20 H 0.8800 0.4834 0.6856 0.047 Uiso 1 1 calc R . . . .
N21 N 0.9273(4) 0.5146(2) 0.79498(14) 0.0590(7) Uani 1 1 d . . . . .
H21A H 0.8450 0.5176 0.8242 0.071 Uiso 1 1 d R . . . .
H21B H 0.9742 0.5632 0.8219 0.071 Uiso 1 1 d R . . . .
C1 C 0.5073(3) 0.65702(15) 0.38942(11) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.6358(3) 0.52917(15) 0.34079(11) 0.0192(4) Uani 1 1 d . . . . .
C3 C 0.7733(2) 0.45522(14) 0.44379(11) 0.0187(4) Uani 1 1 d . . . . .
C4 C 0.7403(3) 0.60043(18) 0.69331(13) 0.0291(5) Uani 1 1 d . . . . .
N12 N 0.2744(3) 1.10933(15) 0.43518(11) 0.0345(5) Uani 1 1 d . . . . .
H12A H 0.1971 1.1217 0.3953 0.041 Uiso 1 1 d R . . . .
H12B H 0.3688 1.1418 0.4274 0.041 Uiso 1 1 d R . . . .
N13 N 0.2170(3) 1.14757(15) 0.50219(12) 0.0380(5) Uani 1 1 d . . . . .
H13 H 0.1927 1.2096 0.5054 0.046 Uiso 1 1 calc R . . . .
N14 N 0.1431(3) 1.12080(17) 0.62296(14) 0.0442(6) Uani 1 1 d . . . . .
H14A H 0.1356 1.0817 0.6612 0.053 Uiso 1 1 calc R . . . .
H14B H 0.1130 1.1821 0.6255 0.053 Uiso 1 1 calc R . . . .
N15 N 0.2477(3) 0.99301(14) 0.55528(11) 0.0314(5) Uani 1 1 d . . . . .
H15 H 0.2906 0.9719 0.5154 0.038 Uiso 1 1 calc R . . . .
N16 N 0.2260(3) 0.92781(16) 0.61674(12) 0.0426(5) Uani 1 1 d . . . . .
H16A H 0.3355 0.9180 0.6407 0.051 Uiso 1 1 d R . . . .
H16B H 0.1725 0.8736 0.5939 0.051 Uiso 1 1 d R . . . .
C5 C 0.2009(3) 1.08671(17) 0.56016(14) 0.0288(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
O1 N1 1.237(2) . ?
O2 N1 1.261(2) . ?
O3 N3 1.243(2) . ?
O4 N3 1.269(2) . ?
O5 N11 1.247(2) . ?
O6 N11 1.249(2) . ?
N1 N2 1.330(2) . ?
N2 C1 1.361(3) . ?
N3 N4 1.331(2) . ?
N4 N5 1.399(2) . ?
N5 C1 1.401(3) . ?
N5 C2 1.365(3) . ?
N6 N7 1.403(2) . ?
N6 C2 1.307(3) . ?
N7 H7 0.8600 . ?
N7 C3 1.344(3) . ?
N8 N9 1.390(2) . ?
N8 C2 1.347(3) . ?
N8 C3 1.351(3) . ?
N9 C1 1.323(3) . ?
N10 N11 1.325(2) . ?
N10 C3 1.356(3) . ?
N17 H17A 0.8695 . ?
N17 H17B 0.8699 . ?
N17 N18 1.419(3) . ?
N18 H18 0.8600 . ?
N18 C4 1.322(3) . ?
N19 H19A 0.8600 . ?
N19 H19B 0.8600 . ?
N19 C4 1.303(3) . ?
N20 H20 0.8600 . ?
N20 N21 1.377(3) . ?
N20 C4 1.356(3) . ?
N21 H21A 0.8659 . ?
N21 H21B 0.8538 . ?
N12 H12A 0.8610 . ?
N12 H12B 0.8698 . ?
N12 N13 1.406(3) . ?
N13 H13 0.8600 . ?
N13 C5 1.323(3) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
N14 C5 1.323(3) . ?
N15 H15 0.8600 . ?
N15 N16 1.416(3) . ?
N15 C5 1.319(3) . ?
N16 H16A 0.8882 . ?
N16 H16B 0.9017 . ?

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 N1 O2 121.69(17) . . ?
O1 N1 N2 124.74(17) . . ?
O2 N1 N2 113.56(16) . . ?
N1 N2 C1 116.86(17) . . ?
O3 N3 O4 121.57(17) . . ?
O3 N3 N4 123.87(17) . . ?
O4 N3 N4 114.56(16) . . ?
N3 N4 N5 108.12(15) . . ?
N4 N5 C1 125.92(16) . . ?
C2 N5 N4 127.74(17) . . ?
C2 N5 C1 106.25(16) . . ?
C2 N6 N7 100.73(16) . . ?
N6 N7 H7 123.2 . . ?
C3 N7 N6 113.69(16) . . ?
C3 N7 H7 123.2 . . ?
C2 N8 N9 114.86(16) . . ?
C2 N8 C3 108.30(17) . . ?
C3 N8 N9 136.83(17) . . ?
C1 N9 N8 101.11(16) . . ?
N11 N10 C3 115.58(17) . . ?
O5 N11 O6 122.01(17) . . ?
O5 N11 N10 121.21(17) . . ?
O6 N11 N10 116.78(17) . . ?
H17A N17 H17B 110.6 . . ?
N18 N17 H17A 108.0 . . ?
N18 N17 H17B 106.9 . . ?
N17 N18 H18 121.3 . . ?
C4 N18 N17 117.33(18) . . ?
C4 N18 H18 121.3 . . ?
H19A N19 H19B 120.0 . . ?
C4 N19 H19A 120.0 . . ?
C4 N19 H19B 120.0 . . ?
N21 N20 H20 118.3 . . ?
C4 N20 H20 118.3 . . ?
C4 N20 N21 123.4(2) . . ?
N20 N21 H21A 109.5 . . ?
N20 N21 H21B 121.9 . . ?
H21A N21 H21B 85.6 . . ?
N2 C1 N5 114.11(17) . . ?
N9 C1 N2 132.65(19) . . ?
N9 C1 N5 113.21(17) . . ?
N6 C2 N5 141.65(19) . . ?
N6 C2 N8 113.79(18) . . ?
N8 C2 N5 104.52(17) . . ?
N7 C3 N8 103.49(17) . . ?
N7 C3 N10 138.06(18) . . ?
N8 C3 N10 118.44(18) . . ?
N18 C4 N20 121.0(2) . . ?
N19 C4 N18 120.7(2) . . ?
N19 C4 N20 118.2(2) . . ?
H12A N12 H12B 105.1 . . ?
N13 N12 H12A 110.0 . . ?
N13 N12 H12B 108.1 . . ?
N12 N13 H13 120.5 . . ?
C5 N13 N12 119.02(19) . . ?
C5 N13 H13 120.5 . . ?
H14A N14 H14B 120.0 . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
N16 N15 H15 120.6 . . ?
C5 N15 H15 120.6 . . ?
C5 N15 N16 118.9(2) . . ?
N15 N16 H16A 104.1 . . ?
N15 N16 H16B 105.2 . . ?
H16A N16 H16B 114.9 . . ?
N13 C5 N14 119.9(2) . . ?
N15 C5 N13 119.2(2) . . ?
N15 C5 N14 120.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.843
