# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 1940001'
loop_
_audit_author_name
_audit_author_address
'Fengcai Li'
;ocean university of china
China
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-10
_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         'C11 H7 O3, H2 O, C3 H7 N6'
_chemical_formula_sum            'C14 H16 N6 O4'
_chemical_formula_weight         332.33
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   35.3301(11)
_cell_length_b                   10.8822(3)
_cell_length_c                   7.5873(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2917.08(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6435
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      2.306
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1306 before and 0.0667 after correction. The Ratio of minimum to maximum transmission is 0.9186. 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    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22152
_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         27.501
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      100.0
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2531
_reflns_number_total             3332
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.077
_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)+(0.0290P)²+2.9191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1078
_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 O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4a,H4b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C9(H9), C8(H8), C11(H11), C4(H4)
2.c X=CH2 refined with riding coordinates:
 N3(H3a,H3b), N1(H1a,H1b), N6(H6a,H6b)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.60314(4) 0.40072(11) 0.16758(19) 0.0180(3) Uani 1 1 d . . . . .
O1 O 0.84636(3) 0.29406(11) 0.06194(19) 0.0170(3) Uani 1 1 d . . . . .
H1 H 0.847147 0.219009 0.087534 0.025 Uiso 1 1 calc GR . . . .
O2 O 0.62801(4) 0.58865(11) 0.17163(19) 0.0193(3) Uani 1 1 d . . . . .
O4 O 0.59949(4) 0.16449(12) 0.2924(2) 0.0218(3) Uani 1 1 d . . . . .
H4A H 0.601755 0.233524 0.235524 0.033 Uiso 1 1 d G . . . .
H4B H 0.616761 0.167875 0.373920 0.033 Uiso 1 1 d G . . . .
N5 N 0.56662(4) 0.70253(14) 0.3134(2) 0.0149(3) Uani 1 1 d . . . . .
N4 N 0.50965(4) 0.67341(13) 0.4697(2) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.53440(4) 0.87688(13) 0.4171(2) 0.0151(3) Uani 1 1 d . . . . .
N3 N 0.47776(4) 0.84729(14) 0.5535(2) 0.0172(4) Uani 1 1 d . . . . .
H3A H 0.459619 0.799916 0.594669 0.021 Uiso 1 1 calc R . . . .
H3B H 0.475807 0.927700 0.561750 0.021 Uiso 1 1 calc R . . . .
N1 N 0.59136(4) 0.89635(14) 0.2730(2) 0.0178(4) Uani 1 1 d . . . . .
H1A H 0.590254 0.976681 0.285238 0.021 Uiso 1 1 calc R . . . .
H1B H 0.610790 0.862455 0.219122 0.021 Uiso 1 1 calc R . . . .
N6 N 0.54288(4) 0.50860(14) 0.3580(2) 0.0173(4) Uani 1 1 d . . . . .
H6A H 0.525622 0.457826 0.399079 0.021 Uiso 1 1 calc R . . . .
H6B H 0.562579 0.479734 0.300316 0.021 Uiso 1 1 calc R . . . .
C5 C 0.74198(5) 0.31979(16) 0.0620(2) 0.0130(4) Uani 1 1 d . . . . .
C14 C 0.56374(5) 0.82633(16) 0.3358(3) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.50797(5) 0.79766(16) 0.4792(3) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.77883(5) 0.27188(16) 0.0319(2) 0.0139(4) Uani 1 1 d . . . . .
H6 H 0.781863 0.194651 -0.024783 0.017 Uiso 1 1 calc R . . . .
C10 C 0.73801(5) 0.43520(16) 0.1470(2) 0.0130(4) Uani 1 1 d . . . . .
C3 C 0.67367(5) 0.30431(16) 0.0402(3) 0.0147(4) Uani 1 1 d . . . . .
H3 H 0.651835 0.259510 0.005346 0.018 Uiso 1 1 calc R . . . .
C9 C 0.77105(5) 0.50053(17) 0.1960(2) 0.0145(4) Uani 1 1 d . . . . .
H9 H 0.768707 0.578160 0.252230 0.017 Uiso 1 1 calc R . . . .
C12 C 0.53925(5) 0.62735(16) 0.3827(3) 0.0147(4) Uani 1 1 d . . . . .
C8 C 0.80629(5) 0.45348(16) 0.1636(3) 0.0146(4) Uani 1 1 d . . . . .
H8 H 0.828207 0.499283 0.194339 0.018 Uiso 1 1 calc R . . . .
C11 C 0.70114(5) 0.48288(16) 0.1766(3) 0.0142(4) Uani 1 1 d . . . . .
H11 H 0.698339 0.559983 0.233860 0.017 Uiso 1 1 calc R . . . .
C2 C 0.66943(5) 0.41960(16) 0.1241(2) 0.0139(4) Uani 1 1 d . . . . .
C1 C 0.63084(5) 0.47232(16) 0.1557(3) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.70880(5) 0.25669(16) 0.0087(2) 0.0143(4) Uani 1 1 d . . . . .
H4 H 0.711030 0.179928 -0.050064 0.017 Uiso 1 1 calc R . . . .
C7 C 0.80999(5) 0.33720(16) 0.0846(3) 0.0141(4) Uani 1 1 d . . . . .
H5 H 0.5882(7) 0.665(2) 0.262(3) 0.038(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 C1 1.254(2) . ?
O1 H1 0.8400 . ?
O1 C7 1.379(2) . ?
O2 C1 1.276(2) . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8696 . ?
N5 C14 1.362(2) . ?
N5 C12 1.371(2) . ?
N5 H5 0.95(3) . ?
N4 C13 1.355(2) . ?
N4 C12 1.334(2) . ?
N2 C14 1.326(2) . ?
N2 C13 1.356(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C13 1.322(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C14 1.327(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C12 1.312(2) . ?
C5 C6 1.421(2) . ?
C5 C10 1.419(2) . ?
C5 C4 1.418(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(3) . ?
C10 C9 1.416(2) . ?
C10 C11 1.420(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.415(3) . ?
C3 C4 1.366(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.369(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.406(3) . ?
C11 H11 0.9500 . ?
C11 C2 1.374(2) . ?
C2 C1 1.498(2) . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 109.5 . . ?
H4A O4 H4B 104.6 . . ?
C14 N5 C12 119.32(16) . . ?
C14 N5 H5 122.5(14) . . ?
C12 N5 H5 117.9(14) . . ?
C12 N4 C13 115.81(15) . . ?
C14 N2 C13 115.88(15) . . ?
H3A N3 H3B 120.0 . . ?
C13 N3 H3A 120.0 . . ?
C13 N3 H3B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C14 N1 H1A 120.0 . . ?
C14 N1 H1B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
C10 C5 C6 119.24(16) . . ?
C4 C5 C6 122.28(16) . . ?
C4 C5 C10 118.48(16) . . ?
N2 C14 N5 121.81(16) . . ?
N2 C14 N1 120.26(16) . . ?
N1 C14 N5 117.93(17) . . ?
N4 C13 N2 125.86(16) . . ?
N3 C13 N4 117.75(16) . . ?
N3 C13 N2 116.39(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.93(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C10 C11 119.08(16) . . ?
C9 C10 C5 118.83(16) . . ?
C9 C10 C11 122.07(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.75(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 120.98(17) . . ?
C8 C9 H9 119.5 . . ?
N4 C12 N5 121.20(16) . . ?
N6 C12 N5 117.64(17) . . ?
N6 C12 N4 121.15(17) . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.86(17) . . ?
C7 C8 H8 120.1 . . ?
C10 C11 H11 119.4 . . ?
C2 C11 C10 121.25(17) . . ?
C2 C11 H11 119.4 . . ?
C3 C2 C1 120.52(16) . . ?
C11 C2 C3 119.26(16) . . ?
C11 C2 C1 120.22(16) . . ?
O3 C1 O2 123.26(17) . . ?
O3 C1 C2 118.93(16) . . ?
O2 C1 C2 117.81(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.17(17) . . ?
C3 C4 H4 119.4 . . ?
O1 C7 C8 116.49(16) . . ?
C6 C7 O1 122.40(16) . . ?
C6 C7 C8 121.10(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
_geom_hbond_publ_flag
O1 H1 O2 0.84 1.79 2.5514(18) 150.6 8_755 yes
O4 H4A O3 0.87 1.89 2.7427(18) 165.5 . yes
O4 H4B O1 0.87 1.98 2.8366(19) 170.1 2_655 yes
N6 H6B O3 0.88 1.95 2.828(2) 174.1 . 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_zz_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1940002'
loop_
_audit_author_name
_audit_author_address
'Fengcai Li'
;ocean university of china
China
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_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         'C11 H7 O3, C3 H7 N6, C3 H7 N O'
_chemical_formula_sum            'C17 H21 N7 O4'
_chemical_formula_weight         387.41
_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                   7.0401(2)
_cell_length_b                   21.0320(8)
_cell_length_c                   12.0394(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.150(12)
_cell_angle_gamma                90
_cell_volume                     1782.64(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5025
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.282
_cell_measurement_theta_min      2.571
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1408 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.9421. 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    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.298
_diffrn_reflns_theta_min         2.572
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_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                3056
_reflns_number_total             5012
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.057
_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)+(0.0501P)²+0.9017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1435
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N7-C16 \\sim N7-C17 \\sim N7-C18 \\sim N7-C19
 with sigma of 0.02
 N7-C15 \\sim N7-C20
 with sigma of 0.02
 O4-C20 \\sim O4-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C20) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: C15(0.85) H15(0.85) C19(0.85) H19A(0.85) H19B(0.85) H19C(0.85)
 C17(0.85) H17A(0.85) H17B(0.85) H17C(0.85) C20(0.15) H20(0.15) C16(0.15)
 H16A(0.15) H16B(0.15) H16C(0.15) C18(0.15) H18A(0.15) H18B(0.15) H18C(0.15)
5.a Aromatic/amide H refined with riding coordinates:
 N3(H3B), C10(H10), C3(H3A), C5(H5), C8(H8), C7(H7), C6(H6), C15(H15), C20(H20)
5.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B), N1(H1A,H1B)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.3455(2) 0.46946(6) 0.32912(12) 0.0250(3) Uani 1 1 d . . . . .
O1 O 0.32161(19) 0.44294(6) 0.50787(12) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.2650(2) 0.57795(6) 0.26415(11) 0.0251(3) Uani 1 1 d . . . . .
H3 H 0.305680 0.540407 0.262943 0.038 Uiso 1 1 calc GR . . . .
N3 N 0.4431(2) 0.33058(7) 0.44868(12) 0.0166(3) Uani 1 1 d . . . . .
H3B H 0.409160 0.370698 0.454586 0.020 Uiso 1 1 calc R . . . .
N2 N 0.5406(2) 0.24519(7) 0.33731(13) 0.0179(3) Uani 1 1 d . . . . .
N4 N 0.5080(2) 0.23277(7) 0.53585(13) 0.0174(3) Uani 1 1 d . . . . .
O4 O 0.6699(3) 0.05499(7) 0.58702(13) 0.0408(4) Uani 1 1 d D . . . .
N5 N 0.3949(2) 0.31835(7) 0.63571(13) 0.0198(3) Uani 1 1 d . . . . .
H5A H 0.396770 0.295455 0.696875 0.024 Uiso 1 1 calc R . . . .
H5B H 0.356671 0.358166 0.637851 0.024 Uiso 1 1 calc R . . . .
N6 N 0.6139(2) 0.15220(7) 0.42463(14) 0.0216(4) Uani 1 1 d . . . . .
H6A H 0.642797 0.136300 0.359201 0.026 Uiso 1 1 calc R . . . .
H6B H 0.624914 0.128564 0.484617 0.026 Uiso 1 1 calc R . . . .
N1 N 0.4822(2) 0.34347(7) 0.26077(13) 0.0205(4) Uani 1 1 d . . . . .
H1A H 0.511665 0.328488 0.194775 0.025 Uiso 1 1 calc R . . . .
H1B H 0.448206 0.383500 0.268267 0.025 Uiso 1 1 calc R . . . .
N7 N 0.7810(2) -0.04490(8) 0.55638(16) 0.0296(4) Uani 1 1 d D . . . .
C14 C 0.5538(3) 0.21193(8) 0.43284(15) 0.0170(4) Uani 1 1 d . . . . .
C12 C 0.4500(2) 0.29279(8) 0.54001(15) 0.0171(4) Uani 1 1 d . . . . .
C13 C 0.4890(2) 0.30591(8) 0.34847(15) 0.0170(4) Uani 1 1 d . . . . .
C9 C 0.0806(3) 0.66885(9) 0.49989(16) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.3017(3) 0.48172(9) 0.42951(16) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.2064(3) 0.59264(9) 0.36882(16) 0.0186(4) Uani 1 1 d . . . . .
C10 C 0.1370(3) 0.65224(9) 0.39107(16) 0.0205(4) Uani 1 1 d . . . . .
H10 H 0.126811 0.682585 0.332909 0.025 Uiso 1 1 calc R . . . .
C4 C 0.0948(3) 0.62282(9) 0.58634(16) 0.0197(4) Uani 1 1 d . . . . .
C2 C 0.2230(3) 0.54649(8) 0.45438(16) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.1666(3) 0.56203(9) 0.56004(16) 0.0202(4) Uani 1 1 d . . . . .
H3A H 0.176277 0.530974 0.617069 0.024 Uiso 1 1 calc R . . . .
C5 C 0.0389(3) 0.63939(10) 0.69534(17) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.047875 0.608806 0.753183 0.029 Uiso 1 1 calc R . . . .
C8 C 0.0131(3) 0.73063(9) 0.52802(17) 0.0238(4) Uani 1 1 d . . . . .
H8 H 0.004433 0.762322 0.472011 0.029 Uiso 1 1 calc R . . . .
C7 C -0.0392(3) 0.74497(10) 0.63378(18) 0.0264(5) Uani 1 1 d . . . . .
H7 H -0.083693 0.786489 0.650706 0.032 Uiso 1 1 calc R . . . .
C6 C -0.0279(3) 0.69900(10) 0.71828(18) 0.0270(5) Uani 1 1 d . . . . .
H6 H -0.066918 0.709369 0.791561 0.032 Uiso 1 1 calc R . . . .
C15 C 0.7252(3) 0.01174(11) 0.5233(2) 0.0267(5) Uani 0.85 1 d D . P A 1
H15 H 0.727029 0.020419 0.445856 0.032 Uiso 0.85 1 calc R . P A 1
C19 C 0.7873(4) -0.06336(13) 0.6718(2) 0.0334(6) Uani 0.85 1 d D . P A 1
H19A H 0.919861 -0.068120 0.695415 0.050 Uiso 0.85 1 calc GR . P A 1
H19B H 0.720592 -0.103879 0.681365 0.050 Uiso 0.85 1 calc GR . P A 1
H19C H 0.725688 -0.030598 0.717035 0.050 Uiso 0.85 1 calc GR . P A 1
C17 C 0.8365(4) -0.09379(12) 0.4743(2) 0.0333(6) Uani 0.85 1 d D . P A 1
H17A H 0.825767 -0.076167 0.399220 0.050 Uiso 0.85 1 calc GR . P A 1
H17B H 0.752509 -0.130720 0.481275 0.050 Uiso 0.85 1 calc GR . P A 1
H17C H 0.968093 -0.106879 0.488117 0.050 Uiso 0.85 1 calc GR . P A 1
C20 C 0.692(2) 0.0041(6) 0.6283(12) 0.040(4) Uani 0.15 1 d D U P A 2
H20 H 0.655951 -0.004578 0.702730 0.048 Uiso 0.15 1 calc R . P A 2
C16 C 0.768(3) -0.0293(9) 0.4425(11) 0.056(5) Uani 0.15 1 d D U P A 2
H16A H 0.654453 -0.048971 0.410533 0.083 Uiso 0.15 1 calc GR . P A 2
H16B H 0.881162 -0.045129 0.403845 0.083 Uiso 0.15 1 calc GR . P A 2
H16C H 0.760577 0.016960 0.434195 0.083 Uiso 0.15 1 calc GR . P A 2
C18 C 0.851(4) -0.0961(10) 0.623(2) 0.078(7) Uani 0.15 1 d D U P A 2
H18A H 0.817717 -0.088509 0.700955 0.116 Uiso 0.15 1 calc GR . P A 2
H18B H 0.989122 -0.098761 0.615765 0.116 Uiso 0.15 1 calc GR . P A 2
H18C H 0.793209 -0.136055 0.598134 0.116 Uiso 0.15 1 calc GR . 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
O2 C1 1.274(2) . ?
O1 C1 1.255(2) . ?
O3 H3 0.8400 . ?
O3 C11 1.363(2) . ?
N3 H3B 0.8800 . ?
N3 C12 1.357(2) . ?
N3 C13 1.353(2) . ?
N2 C14 1.349(2) . ?
N2 C13 1.335(2) . ?
N4 C14 1.355(2) . ?
N4 C12 1.328(2) . ?
O4 C15 1.253(3) . ?
O4 C20 1.190(12) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C12 1.330(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C14 1.329(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C13 1.319(2) . ?
N7 C15 1.316(3) . ?
N7 C19 1.444(3) . ?
N7 C17 1.479(3) . ?
N7 C20 1.485(13) . ?
N7 C16 1.412(13) . ?
N7 C18 1.429(14) . ?
C9 C10 1.414(3) . ?
C9 C4 1.425(3) . ?
C9 C8 1.425(3) . ?
C1 C2 1.501(3) . ?
C11 C10 1.372(3) . ?
C11 C2 1.420(3) . ?
C10 H10 0.9500 . ?
C4 C3 1.411(3) . ?
C4 C5 1.415(3) . ?
C2 C3 1.373(3) . ?
C3 H3A 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.367(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.360(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.406(3) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C20 H20 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 H3 109.5 . . ?
C12 N3 H3B 120.3 . . ?
C13 N3 H3B 120.3 . . ?
C13 N3 C12 119.32(15) . . ?
C13 N2 C14 115.37(16) . . ?
C12 N4 C14 114.58(16) . . ?
H5A N5 H5B 120.0 . . ?
C12 N5 H5A 120.0 . . ?
C12 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C14 N6 H6A 120.0 . . ?
C14 N6 H6B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C13 N1 H1A 120.0 . . ?
C13 N1 H1B 120.0 . . ?
C15 N7 C19 122.9(2) . . ?
C15 N7 C17 120.4(2) . . ?
C19 N7 C17 116.7(2) . . ?
C16 N7 C20 112.3(9) . . ?
C16 N7 C18 137.8(14) . . ?
C18 N7 C20 109.8(13) . . ?
N2 C14 N4 126.62(16) . . ?
N6 C14 N2 116.60(17) . . ?
N6 C14 N4 116.77(17) . . ?
N4 C12 N3 122.44(17) . . ?
N4 C12 N5 120.49(17) . . ?
N5 C12 N3 117.07(16) . . ?
N2 C13 N3 121.48(16) . . ?
N1 C13 N3 118.41(16) . . ?
N1 C13 N2 120.11(17) . . ?
C10 C9 C4 119.33(17) . . ?
C10 C9 C8 122.70(18) . . ?
C8 C9 C4 117.95(18) . . ?
O2 C1 C2 117.58(16) . . ?
O1 C1 O2 123.69(17) . . ?
O1 C1 C2 118.73(17) . . ?
O3 C11 C10 119.78(17) . . ?
O3 C11 C2 119.42(16) . . ?
C10 C11 C2 120.77(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.51(18) . . ?
C11 C10 H10 119.7 . . ?
C3 C4 C9 118.43(17) . . ?
C3 C4 C5 122.15(18) . . ?
C5 C4 C9 119.42(17) . . ?
C11 C2 C1 120.36(17) . . ?
C3 C2 C1 120.57(17) . . ?
C3 C2 C11 119.07(17) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 C4 121.88(17) . . ?
C2 C3 H3A 119.1 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.66(19) . . ?
C6 C5 H5 119.7 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 121.07(19) . . ?
C7 C8 H8 119.5 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.67(19) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 120.21(19) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O4 C15 N7 124.4(2) . . ?
O4 C15 H15 117.8 . . ?
N7 C15 H15 117.8 . . ?
N7 C19 H19A 109.5 . . ?
N7 C19 H19B 109.5 . . ?
N7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N7 C17 H17A 109.5 . . ?
N7 C17 H17B 109.5 . . ?
N7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C20 N7 115.8(11) . . ?
O4 C20 H20 122.1 . . ?
N7 C20 H20 122.1 . . ?
N7 C16 H16A 109.5 . . ?
N7 C16 H16B 109.5 . . ?
N7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
N7 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
