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

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

data_20200806cL_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2033763'
loop_
_audit_author_name
_audit_author_address
'Yanfei Cheng'
;northwest university
China
;
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C9 H9 N13 O4, 2(H2 O)'
_chemical_formula_sum            'C9 H13 N13 O6'
_chemical_formula_weight         399.29
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H -0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01480 0.00700 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04120 0.02500 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.02530 0.01360 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.677(2)
_cell_length_b                   9.036(4)
_cell_length_c                   10.283(4)
_cell_angle_alpha                77.57(3)
_cell_angle_beta                 78.49(3)
_cell_angle_gamma                78.960(19)
_cell_volume                     762.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7080
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      54.890
_cell_measurement_theta_min      4.417
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1147 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.9030. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.7397
_exptl_crystal_description       block
_exptl_crystal_F_000             413.2561
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10801
_diffrn_reflns_theta_full        54.9147
_diffrn_reflns_theta_max         54.91
_diffrn_reflns_theta_min         3.88
_diffrn_ambient_temperature      150.(2)
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.9962
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.34138
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2553
_reflns_number_total             2891
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.4957
_refine_diff_density_min         -0.3148
_refine_diff_density_rms         0.0588
_refine_ls_d_res_high            0.8196
_refine_ls_d_res_low             9.9043
_refine_ls_goodness_of_fit_ref   1.0697
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.0683
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.4853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1044
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O8-H8c = O8-H8d
 0.87 with sigma of 0.02
 O9-H9c = O9-H9d
 0.87 with sigma of 0.02
 H9c-H8c
 2.2 with sigma of 0.02
 H8c-H8d
 1.38 with sigma of 0.04
 H9c-H9d
 1.38 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 N13(H13), N10(H10), C11(H11), C13(H13a), C12(H12)
3.b X=CH2 refined with riding coordinates:
 N8(H8a,H8b), N9(H9a,H9b)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O4 O 0.02608(15) 0.30340(16) 0.60715(14) 0.0332(3) Uani 1.000000 .
O7 O 0.83412(18) 0.82409(16) 0.02987(15) 0.0376(4) Uani 1.000000 .
O6 O 0.69186(18) 1.01734(15) -0.08056(15) 0.0377(4) Uani 1.000000 .
O5 O 0.22374(16) 0.37243(17) 0.66912(14) 0.0366(3) Uani 1.000000 .
O8 O 0.95269(17) -0.0049(2) 0.64136(16) 0.0424(4) Uani 1.000000 D
H8c H 1.011(3) -0.026(3) 0.708(2) 0.0636(6) Uiso 1.000000 DR
H8d H 0.983(3) 0.079(2) 0.600(3) 0.0636(6) Uiso 1.000000 DR
N6 N 0.77564(17) 0.64037(16) -0.09884(14) 0.0212(3) Uani 1.000000 .
N13 N 0.65966(18) 0.11710(17) 0.58510(14) 0.0244(3) Uani 1.000000 .
H13 H 0.73754(18) 0.06359(17) 0.62667(14) 0.0292(4) Uiso 1.000000 R
N3 N 0.62274(16) 0.41134(16) 0.22503(14) 0.0203(3) Uani 1.000000 .
N12 N 0.68019(17) 0.23192(17) 0.47345(14) 0.0242(3) Uani 1.000000 .
N7 N 0.42660(17) 0.20332(16) 0.53579(14) 0.0212(3) Uani 1.000000 .
N10 N 0.94607(17) 0.43848(17) -0.12189(14) 0.0224(3) Uani 1.000000 .
H10 H 1.02744(17) 0.37527(17) -0.15506(14) 0.0269(4) Uiso 1.000000 R
N11 N 0.84400(17) 0.39843(16) -0.00365(14) 0.0223(3) Uani 1.000000 .
N2 N 0.26674(17) 0.20283(17) 0.52610(15) 0.0238(3) Uani 1.000000 .
N1 N 0.17236(17) 0.29558(17) 0.60377(14) 0.0248(3) Uani 1.000000 .
O9 O 1.1395(2) -0.0724(2) 0.83817(17) 0.0488(4) Uani 1.000000 D
H9c H 1.157(4) -0.1702(19) 0.853(3) 0.0733(6) Uiso 1.000000 DR
H9d H 1.156(4) -0.042(3) 0.909(2) 0.0733(6) Uiso 1.000000 DR
N4 N 0.74581(18) 0.87863(17) -0.05664(15) 0.0269(3) Uani 1.000000 .
N5 N 0.69901(18) 0.79229(17) -0.12870(15) 0.0249(3) Uani 1.000000 .
N8 N 0.4495(2) -0.00824(19) 0.71982(16) 0.0311(4) Uani 1.000000 .
H8a H 0.5132(2) -0.07529(19) 0.76851(16) 0.0373(4) Uiso 1.000000 R
H8b H 0.3466(2) -0.01135(19) 0.73614(16) 0.0373(4) Uiso 1.000000 R
N9 N 0.98026(19) 0.65999(18) -0.29207(15) 0.0300(4) Uani 1.000000 .
H9a H 0.94375(19) 0.75706(18) -0.32023(15) 0.0360(4) Uiso 1.000000 R
H9b H 1.06533(19) 0.61401(18) -0.33869(15) 0.0360(4) Uiso 1.000000 R
C10 C 0.6071(2) 0.52987(19) 0.12197(16) 0.0193(3) Uani 1.000000 .
C15 C 0.5379(2) 0.28189(19) 0.44487(17) 0.0211(4) Uani 1.000000 .
C16 C 0.74084(19) 0.52243(19) 0.00870(16) 0.0193(3) Uani 1.000000 .
C14 C 0.5046(2) 0.40738(19) 0.33114(16) 0.0200(4) Uani 1.000000 .
C11 C 0.4759(2) 0.64570(19) 0.11993(17) 0.0213(4) Uani 1.000000 .
H11 H 0.4701(2) 0.72833(19) 0.04537(17) 0.0256(4) Uiso 1.000000 R
C13 C 0.3668(2) 0.5157(2) 0.33780(17) 0.0220(4) Uani 1.000000 .
H13a H 0.2843(2) 0.5068(2) 0.41388(17) 0.0263(4) Uiso 1.000000 R
C18 C 0.9074(2) 0.5834(2) -0.17994(17) 0.0224(4) Uani 1.000000 .
C12 C 0.3538(2) 0.63696(19) 0.22998(17) 0.0218(4) Uani 1.000000 .
H12 H 0.2619(2) 0.71349(19) 0.23144(17) 0.0261(4) Uiso 1.000000 R
C17 C 0.5084(2) 0.0969(2) 0.62241(17) 0.0233(4) Uani 1.000000 .


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
O4 N1 1.252(2) . ?
O7 N4 1.249(2) . ?
O6 N4 1.241(2) . ?
O5 N1 1.254(2) . ?
N6 N5 1.404(2) . ?
N6 C16 1.390(2) . ?
N6 C18 1.359(2) . ?
N13 N12 1.379(2) . ?
N13 C17 1.328(2) . ?
N3 C10 1.342(2) . ?
N3 C14 1.339(2) . ?
N12 C15 1.300(2) . ?
N7 N2 1.411(2) . ?
N7 C15 1.388(2) . ?
N7 C17 1.358(2) . ?
N10 N11 1.377(2) . ?
N10 C18 1.326(2) . ?
N11 C16 1.306(2) . ?
N2 N1 1.332(2) . ?
N4 N5 1.346(2) . ?
N8 C17 1.319(2) . ?
N9 C18 1.319(2) . ?
C10 C16 1.474(2) . ?
C10 C11 1.391(2) . ?
C15 C14 1.475(2) . ?
C14 C13 1.393(2) . ?
C11 C12 1.387(2) . ?
C13 C12 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N6 N5 130.85(14) . . ?
C18 N6 N5 122.20(14) . . ?
C18 N6 C16 106.96(14) . . ?
C17 N13 N12 111.97(14) . . ?
C14 N3 C10 117.07(14) . . ?
C15 N12 N13 104.58(14) . . ?
C15 N7 N2 128.27(14) . . ?
C17 N7 N2 123.40(14) . . ?
C17 N7 C15 106.73(14) . . ?
C18 N10 N11 112.14(14) . . ?
C16 N11 N10 104.73(14) . . ?
N1 N2 N7 108.84(13) . . ?
O5 N1 O4 120.99(15) . . ?
N2 N1 O4 115.66(15) . . ?
N2 N1 O5 123.34(14) . . ?
O6 N4 O7 122.02(16) . . ?
N5 N4 O7 123.09(14) . . ?
N5 N4 O6 114.87(15) . . ?
N4 N5 N6 109.31(13) . . ?
C16 C10 N3 113.15(14) . . ?
C11 C10 N3 123.64(15) . . ?
C11 C10 C16 123.17(15) . . ?
N7 C15 N12 110.89(15) . . ?
C14 C15 N12 122.82(15) . . ?
C14 C15 N7 126.28(15) . . ?
N11 C16 N6 110.42(14) . . ?
C10 C16 N6 126.62(15) . . ?
C10 C16 N11 122.95(15) . . ?
C15 C14 N3 113.56(14) . . ?
C13 C14 N3 123.75(15) . . ?
C13 C14 C15 122.60(15) . . ?
C12 C11 C10 118.04(15) . . ?
C12 C13 C14 117.94(15) . . ?
N10 C18 N6 105.75(14) . . ?
N9 C18 N6 125.93(16) . . ?
N9 C18 N10 128.32(16) . . ?
C13 C12 C11 119.52(15) . . ?
N7 C17 N13 105.79(15) . . ?
N8 C17 N13 127.48(16) . . ?
N8 C17 N7 126.69(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8c O9 0.894(15) 1.845(16) 2.738(2) 177(3) .
N13 H13 O8 0.8800 1.876(2) 2.693(2) 153.63(6) .
N10 H10 O7 0.8800 2.266(2) 2.861(2) 124.75(5) 2_765
N8 H8b O9 0.8800 2.003(2) 2.835(2) 157.37(6) 1_455

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O8 H8c 1 0.8700 0.0200 -0.0241
O8 H8d 1 0.8700 0.0200 0.0259
H8c H8d 1 1.3800 0.0400 0.0607
O9 H9c 1 0.8700 0.0200 0.0169
O9 H9d 1 0.8700 0.0200 -0.0079
H9c H8c 1 2.2000 0.0200 0.0027
H9c H9d 1 1.3800 0.0400 -0.0168

####################################################################### 
# 
# 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_20200806dl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2043055'
loop_
_audit_author_name
_audit_author_address
'Cheng yanfei'
;northwest university
China
;
_audit_update_record             
;
2020-11-08 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-07
_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(C8 H7 N14 O4), 3.5(H2 O), 2(H4 N)'
_chemical_formula_sum            'C16 H29 N30 O11.50'
_chemical_formula_weight         825.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   21.16(5)
_cell_length_b                   13.182(9)
_cell_length_c                   11.89(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.45(18)
_cell_angle_gamma                90
_cell_volume                     3196(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6705
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.687
_cell_measurement_theta_min      3.767
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.7660.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1708
_exptl_crystal_size_max          0.18
_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  0.0470
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18886
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.021
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4140
_reflns_number_total             5793
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5793
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.126
_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)+(0.1200P)²+5.2907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All N(H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H11D-H30D
 2.2 with sigma of 0.02
 H29A-O10
 2.3 with sigma of 0.02
 O10-H29A
 2.2 with sigma of 0.02
 N17-O9
 2 with sigma of 0.02
 O9-O10
 2.8 with sigma of 0.02
 N30-H30D \\sim N30-H30B \\sim N30-H30A \\sim N30-H30C \\sim N29-H29C \\sim
N29-H29D \\sim N29-H29A ~
 N29-H29B
 with sigma of 0.02
3. Others
 Fixed Sof: O9(0.5) H9A(0.5) H9B(0.5)
4.a Free rotating group:
 O11(H11C,H11D), O10(H10A,H10B), O9(H9A,H9B), O12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 N18(H18), N4(H4), C10(H10), C12(H12), C3(H3), C5(H5)
4.c X=CH2 refined with riding coordinates:
 N19(H19A,H19B), N25(H25A,H25B), N11(H11A,H11B), N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 1.13401(13) 0.7989(2) 0.9283(2) 0.0359(6) Uani 1 1 d . . . . .
O2 O 1.22447(12) 0.7354(2) 1.0408(2) 0.0365(7) Uani 1 1 d . . . . .
O8 O 0.27442(13) 0.2677(2) 0.2143(2) 0.0366(7) Uani 1 1 d . . . . .
O6 O 0.65340(14) 0.2033(2) 0.7159(2) 0.0374(7) Uani 1 1 d . . . . .
O3 O 0.84295(14) 0.8055(2) 1.1739(2) 0.0402(7) Uani 1 1 d . . . . .
O4 O 0.75745(12) 0.7378(2) 1.0510(2) 0.0343(6) Uani 1 1 d . . . . .
O5 O 0.74295(12) 0.2710(2) 0.6905(2) 0.0353(7) Uani 1 1 d . . . . .
O7 O 0.35870(15) 0.1986(2) 0.1723(3) 0.0497(8) Uani 1 1 d . . . . .
O11 O 0.80460(15) 0.4584(2) 0.7226(3) 0.0455(7) Uani 1 1 d . . . . .
H11C H 0.838268 0.467212 0.694529 0.068 Uiso 1 1 d G . . . .
H11D H 0.795532 0.394056 0.712208 0.068 Uiso 1 1 d DG . . . .
N17 N 0.51009(15) 0.3815(2) 0.1505(2) 0.0288(7) Uani 1 1 d D . . . .
N18 N 0.47342(15) 0.3804(2) 0.0351(2) 0.0282(7) Uani 1 1 d . . . . .
H18 H 0.489977 0.384597 -0.025284 0.034 Uiso 1 1 calc R . . . .
N20 N 0.40418(14) 0.3673(2) 0.1391(2) 0.0262(7) Uani 1 1 d . . . . .
N21 N 0.34454(15) 0.3696(2) 0.1675(3) 0.0285(7) Uani 1 1 d . . . . .
N22 N 0.32626(15) 0.2745(3) 0.1840(2) 0.0316(7) Uani 1 1 d . . . . .
N19 N 0.36003(16) 0.3684(3) -0.0683(3) 0.0354(8) Uani 1 1 d . . . . .
H19A H 0.367502 0.371715 -0.137534 0.042 Uiso 1 1 calc R . . . .
H19B H 0.319601 0.362725 -0.062323 0.042 Uiso 1 1 calc R . . . .
N26 N 0.61456(14) 0.3693(2) 0.7731(2) 0.0247(7) Uani 1 1 d . . . . .
N27 N 0.67534(15) 0.3720(2) 0.7470(2) 0.0271(7) Uani 1 1 d . . . . .
N28 N 0.68989(15) 0.2789(2) 0.7183(2) 0.0293(7) Uani 1 1 d . . . . .
N25 N 0.65947(15) 0.3730(2) 0.9795(2) 0.0313(7) Uani 1 1 d . . . . .
H25A H 0.653026 0.378186 1.049394 0.038 Uiso 1 1 calc R . . . .
H25B H 0.699546 0.367028 0.971857 0.038 Uiso 1 1 calc R . . . .
N23 N 0.50927(15) 0.3818(2) 0.7630(2) 0.0276(7) Uani 1 1 d . . . . .
N24 N 0.54567(16) 0.3826(2) 0.8796(2) 0.0284(7) Uani 1 1 d . . . . .
N12 N 0.88561(15) 0.6357(2) 1.2524(2) 0.0252(7) Uani 1 1 d . . . . .
N13 N 0.82598(15) 0.6343(2) 1.1658(2) 0.0290(7) Uani 1 1 d . . . . .
N14 N 0.80976(15) 0.7300(2) 1.1324(2) 0.0295(7) Uani 1 1 d . . . . .
N11 N 0.83906(16) 0.6368(3) 1.4125(3) 0.0361(8) Uani 1 1 d . . . . .
H11A H 0.845123 0.633793 1.488599 0.043 Uiso 1 1 calc R . . . .
H11B H 0.799210 0.643585 1.366243 0.043 Uiso 1 1 calc R . . . .
N9 N 0.99060(15) 0.6197(2) 1.3457(2) 0.0261(7) Uani 1 1 d . . . . .
N10 N 0.95301(15) 0.6207(2) 1.4250(2) 0.0276(7) Uani 1 1 d . . . . .
N6 N 1.10037(15) 0.6329(2) 0.8299(2) 0.0288(7) Uani 1 1 d . . . . .
N7 N 1.16119(16) 0.6331(2) 0.9158(3) 0.0316(7) Uani 1 1 d . . . . .
N8 N 1.17263(15) 0.7255(2) 0.9602(2) 0.0294(7) Uani 1 1 d . . . . .
N5 N 1.14804(16) 0.6287(3) 0.6715(3) 0.0361(8) Uani 1 1 d . . . . .
H5A H 1.143312 0.623413 0.595944 0.043 Uiso 1 1 calc R . . . .
H5B H 1.187484 0.634212 0.719618 0.043 Uiso 1 1 calc R . . . .
N4 N 1.03324(15) 0.6206(2) 0.6545(2) 0.0289(7) Uani 1 1 d . . . . .
H4 H 1.017835 0.615791 0.578277 0.035 Uiso 1 1 calc R . . . .
N3 N 0.99612(16) 0.6215(2) 0.7354(2) 0.0290(7) Uani 1 1 d . . . . .
N16 N 0.44214(15) 0.3733(2) 0.3991(2) 0.0288(7) Uani 1 1 d . . . . .
N15 N 0.57655(15) 0.3650(3) 0.5140(3) 0.0340(8) Uani 1 1 d . . . . .
N2 N 0.92574(15) 0.6297(2) 1.0320(2) 0.0308(7) Uani 1 1 d . . . . .
N1 N 1.06049(15) 0.6371(2) 1.0495(2) 0.0302(7) Uani 1 1 d . . . . .
N30 N 0.78749(17) 0.5330(3) 0.9274(3) 0.0371(8) Uani 1 1 d D . . . .
H30A H 0.794(2) 0.477(3) 0.982(3) 0.056 Uiso 1 1 d DR . . . .
H30B H 0.814(2) 0.591(2) 0.954(4) 0.056 Uiso 1 1 d DR . . . .
H30C H 0.7428(12) 0.558(3) 0.910(4) 0.056 Uiso 1 1 d DR . . . .
H30D H 0.793(2) 0.505(3) 0.853(3) 0.056 Uiso 1 1 d DR . . . .
C11 C 0.48755(18) 0.3694(3) 0.3399(3) 0.0260(8) Uani 1 1 d . . . . .
C15 C 0.40998(18) 0.3720(3) 0.0277(3) 0.0277(8) Uani 1 1 d . . . . .
C6 C 1.03705(18) 0.6295(3) 0.8394(3) 0.0267(8) Uani 1 1 d . . . . .
C7 C 1.09586(18) 0.6282(3) 0.7129(3) 0.0267(8) Uani 1 1 d . . . . .
C4 C 0.97085(18) 0.6328(3) 1.1356(3) 0.0266(8) Uani 1 1 d . . . . .
C14 C 0.46726(18) 0.3725(3) 0.2120(3) 0.0264(8) Uani 1 1 d . . . . .
C9 C 0.88893(19) 0.6311(3) 1.3685(3) 0.0278(8) Uani 1 1 d . . . . .
C16 C 0.55107(18) 0.3739(3) 0.7009(3) 0.0246(8) Uani 1 1 d . . . . .
C8 C 0.94903(17) 0.6293(3) 1.2427(3) 0.0234(7) Uani 1 1 d . . . . .
C17 C 0.60872(18) 0.3742(3) 0.8855(3) 0.0251(8) Uani 1 1 d . . . . .
C2 C 1.01530(17) 0.6322(3) 0.9466(3) 0.0249(8) Uani 1 1 d . . . . .
C13 C 0.53082(18) 0.3702(3) 0.5731(3) 0.0249(8) Uani 1 1 d . . . . .
C10 C 0.55447(19) 0.3637(3) 0.3974(3) 0.0333(9) Uani 1 1 d . . . . .
H10 H 0.585226 0.358792 0.352247 0.040 Uiso 1 1 calc R . . . .
C12 C 0.46418(19) 0.3721(3) 0.5160(3) 0.0295(8) Uani 1 1 d . . . . .
H12 H 0.433301 0.372470 0.561157 0.035 Uiso 1 1 calc R . . . .
C3 C 0.94839(18) 0.6304(3) 0.9378(3) 0.0313(9) Uani 1 1 d . . . . .
H3 H 0.918146 0.629606 0.862727 0.038 Uiso 1 1 calc R . . . .
C5 C 1.03740(18) 0.6375(3) 1.1433(3) 0.0294(8) Uani 1 1 d . . . . .
H5 H 1.067603 0.641136 1.218339 0.035 Uiso 1 1 calc R . . . .
O10 O 0.7161(2) 0.4445(4) 0.4150(3) 0.0732(11) Uani 1 1 d D . . . .
H10A H 0.712171 0.384047 0.384486 0.110 Uiso 1 1 d G . . . .
H10B H 0.691962 0.482818 0.360731 0.110 Uiso 1 1 d G . . . .
O9 O 0.6085(3) 0.5059(5) 0.2290(6) 0.0610(18) Uani 0.5 1 d D . P . .
H9A H 0.642856 0.527437 0.209170 0.092 Uiso 0.5 1 d G . P . .
H9B H 0.596928 0.556796 0.265714 0.092 Uiso 0.5 1 d G . P . .
O12 O 0.89295(14) 0.5097(2) 0.6085(2) 0.0438(7) Uani 1 1 d . . . . .
H12A H 0.916995 0.456931 0.604762 0.066 Uiso 1 1 d G . . . .
H12B H 0.917686 0.547240 0.663144 0.066 Uiso 1 1 d G . . . .
N29 N 0.69713(17) 0.5695(3) 0.5916(3) 0.0402(8) Uani 1 1 d D . . . .
H29A H 0.6779(19) 0.566(3) 0.5097(18) 0.060 Uiso 1 1 d DR . . . .
H29B H 0.6597(17) 0.583(4) 0.621(4) 0.060 Uiso 1 1 d DR . . . .
H29C H 0.7286(19) 0.531(3) 0.648(3) 0.060 Uiso 1 1 d DR . . . .
H29D H 0.713(2) 0.636(2) 0.581(5) 0.060 Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N8 1.257(4) . ?
O2 N8 1.256(5) . ?
O8 N22 1.245(5) . ?
O6 N28 1.256(4) . ?
O3 N14 1.242(4) . ?
O4 N14 1.266(5) . ?
O5 N28 1.256(5) . ?
O7 N22 1.243(4) . ?
O11 H11C 0.8709 . ?
O11 H11D 0.8705 . ?
N17 N18 1.385(5) . ?
N17 C14 1.313(5) . ?
N18 H18 0.8800 . ?
N18 C15 1.326(6) . ?
N20 N21 1.391(5) . ?
N20 C15 1.363(5) . ?
N20 C14 1.386(6) . ?
N21 N22 1.341(4) . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
N19 C15 1.334(6) . ?
N26 N27 1.401(5) . ?
N26 C16 1.389(6) . ?
N26 C17 1.376(5) . ?
N27 N28 1.332(4) . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N25 C17 1.328(6) . ?
N23 N24 1.395(5) . ?
N23 C16 1.298(5) . ?
N24 C17 1.321(6) . ?
N12 N13 1.400(5) . ?
N12 C9 1.364(5) . ?
N12 C8 1.380(6) . ?
N13 N14 1.339(4) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C9 1.299(6) . ?
N9 N10 1.386(5) . ?
N9 C8 1.309(5) . ?
N10 C9 1.350(6) . ?
N6 N7 1.414(6) . ?
N6 C6 1.375(6) . ?
N6 C7 1.370(5) . ?
N7 N8 1.325(4) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C7 1.323(6) . ?
N4 H4 0.8800 . ?
N4 N3 1.395(5) . ?
N4 C7 1.326(6) . ?
N3 C6 1.311(5) . ?
N16 C11 1.335(5) . ?
N16 C12 1.342(5) . ?
N15 C13 1.340(5) . ?
N15 C10 1.339(5) . ?
N2 C4 1.343(6) . ?
N2 C3 1.329(5) . ?
N1 C2 1.339(5) . ?
N1 C5 1.331(5) . ?
N30 H30A 0.97(2) . ?
N30 H30B 0.96(2) . ?
N30 H30C 0.97(2) . ?
N30 H30D 0.994(18) . ?
C11 C14 1.466(6) . ?
C11 C10 1.401(6) . ?
C6 C2 1.466(6) . ?
C4 C8 1.466(5) . ?
C4 C5 1.388(6) . ?
C16 C13 1.465(5) . ?
C2 C3 1.392(6) . ?
C13 C12 1.393(6) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
O10 H10A 0.8704 . ?
O10 H10B 0.8695 . ?
O9 H9A 0.8702 . ?
O9 H9B 0.8700 . ?
O12 H12A 0.8699 . ?
O12 H12B 0.8714 . ?
N29 H29A 0.95(2) . ?
N29 H29B 0.96(2) . ?
N29 H29C 0.96(2) . ?
N29 H29D 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H11C O11 H11D 104.4 . . ?
C14 N17 N18 105.3(3) . . ?
N17 N18 H18 124.6 . . ?
C15 N18 N17 110.9(3) . . ?
C15 N18 H18 124.6 . . ?
C15 N20 N21 123.9(3) . . ?
C15 N20 C14 106.5(3) . . ?
C14 N20 N21 129.2(3) . . ?
N22 N21 N20 109.3(3) . . ?
O8 N22 N21 114.8(3) . . ?
O7 N22 O8 122.0(3) . . ?
O7 N22 N21 123.2(3) . . ?
H19A N19 H19B 120.0 . . ?
C15 N19 H19A 120.0 . . ?
C15 N19 H19B 120.0 . . ?
C16 N26 N27 131.0(3) . . ?
C17 N26 N27 122.6(3) . . ?
C17 N26 C16 106.0(3) . . ?
N28 N27 N26 108.7(3) . . ?
O6 N28 N27 123.6(3) . . ?
O5 N28 O6 121.0(3) . . ?
O5 N28 N27 115.3(3) . . ?
H25A N25 H25B 120.0 . . ?
C17 N25 H25A 120.0 . . ?
C17 N25 H25B 120.0 . . ?
C16 N23 N24 106.6(3) . . ?
C17 N24 N23 109.5(3) . . ?
C9 N12 N13 122.5(3) . . ?
C9 N12 C8 107.0(3) . . ?
C8 N12 N13 130.1(3) . . ?
N14 N13 N12 108.3(3) . . ?
O3 N14 O4 121.7(3) . . ?
O3 N14 N13 124.3(3) . . ?
O4 N14 N13 114.0(3) . . ?
H11A N11 H11B 120.0 . . ?
C9 N11 H11A 120.0 . . ?
C9 N11 H11B 120.0 . . ?
C8 N9 N10 105.7(3) . . ?
C9 N10 N9 110.2(3) . . ?
C6 N6 N7 131.3(3) . . ?
C7 N6 N7 122.5(3) . . ?
C7 N6 C6 106.0(3) . . ?
N8 N7 N6 108.9(3) . . ?
O1 N8 N7 123.6(3) . . ?
O2 N8 O1 121.0(3) . . ?
O2 N8 N7 115.4(3) . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
N3 N4 H4 126.1 . . ?
C7 N4 H4 126.1 . . ?
C7 N4 N3 107.8(3) . . ?
C6 N3 N4 107.4(3) . . ?
C11 N16 C12 116.4(4) . . ?
C10 N15 C13 116.2(4) . . ?
C3 N2 C4 116.4(4) . . ?
C5 N1 C2 115.7(4) . . ?
H30A N30 H30B 116(4) . . ?
H30A N30 H30C 110(4) . . ?
H30A N30 H30D 107(4) . . ?
H30B N30 H30C 105(4) . . ?
H30B N30 H30D 112(4) . . ?
H30C N30 H30D 107(4) . . ?
N16 C11 C14 119.5(4) . . ?
N16 C11 C10 121.4(4) . . ?
C10 C11 C14 119.1(4) . . ?
N18 C15 N20 106.9(3) . . ?
N18 C15 N19 128.1(4) . . ?
N19 C15 N20 125.0(4) . . ?
N6 C6 C2 127.5(3) . . ?
N3 C6 N6 109.8(3) . . ?
N3 C6 C2 122.7(4) . . ?
N5 C7 N6 122.5(4) . . ?
N5 C7 N4 128.5(3) . . ?
N4 C7 N6 108.9(4) . . ?
N2 C4 C8 119.0(4) . . ?
N2 C4 C5 121.5(4) . . ?
C5 C4 C8 119.5(4) . . ?
N17 C14 N20 110.4(3) . . ?
N17 C14 C11 121.7(4) . . ?
N20 C14 C11 127.9(4) . . ?
N11 C9 N12 125.2(4) . . ?
N11 C9 N10 128.4(3) . . ?
N10 C9 N12 106.4(4) . . ?
N26 C16 C13 127.3(4) . . ?
N23 C16 N26 110.2(3) . . ?
N23 C16 C13 122.5(4) . . ?
N12 C8 C4 127.5(3) . . ?
N9 C8 N12 110.7(3) . . ?
N9 C8 C4 121.8(4) . . ?
N25 C17 N26 123.7(4) . . ?
N24 C17 N26 107.6(3) . . ?
N24 C17 N25 128.6(3) . . ?
N1 C2 C6 118.9(4) . . ?
N1 C2 C3 122.3(4) . . ?
C3 C2 C6 118.9(3) . . ?
N15 C13 C16 119.5(4) . . ?
N15 C13 C12 121.6(4) . . ?
C12 C13 C16 118.9(4) . . ?
N15 C10 C11 122.2(4) . . ?
N15 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
N16 C12 C13 122.2(4) . . ?
N16 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N2 C3 C2 121.6(4) . . ?
N2 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
H10A O10 H10B 104.5 . . ?
H9A O9 H9B 104.5 . . ?
H12A O12 H12B 104.4 . . ?
H29A N29 H29B 102(4) . . ?
H29A N29 H29C 136(3) . . ?
H29A N29 H29D 89(4) . . ?
H29B N29 H29C 109(4) . . ?
H29B N29 H29D 103(4) . . ?
H29C N29 H29D 113(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
