# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2059472'
loop_
_audit_author_name
_audit_author_address
'Chen Wang'
;College of Chemistry and Chemical Engineering, Liaoning Normal University
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H14 N6 O6, C7 H5'
_chemical_formula_sum            'C33 H19 N6 O6'
_chemical_formula_weight         595.54
_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                   10.7535(7)
_cell_length_b                   8.9587(6)
_cell_length_c                   27.8995(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.3210(10)
_cell_angle_gamma                90
_cell_volume                     2671.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2180
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.94
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6407
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.8592.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16538
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_min         1.469
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3138
_reflns_number_total             6468
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXD-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      0.995
_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)+(0.0828P)²+0.0433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1774
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C14(H14), C15(H15), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), N2(H2),
 N5(H5)
;
_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
C1 C 0.6865(2) 1.0344(3) 0.03478(8) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.6512(2) 0.9426(3) -0.00591(8) 0.0313(5) Uani 1 1 d . . . . .
C3 C 0.7198(2) 1.1841(3) 0.02744(9) 0.0357(6) Uani 1 1 d . . . . .
C4 C 0.6235(2) 0.7909(3) 0.00110(9) 0.0353(6) Uani 1 1 d . . . . .
C5 C 0.7686(2) 1.2780(3) 0.06886(9) 0.0408(6) Uani 1 1 d . . . . .
C6 C 0.6472(2) 1.0062(3) -0.05254(8) 0.0361(6) Uani 1 1 d . . . . .
C7 C 0.7141(2) 1.2430(3) -0.01822(9) 0.0439(7) Uani 1 1 d . . . . .
H7 H 0.735760 1.342162 -0.022568 0.053 Uiso 1 1 calc R . . . .
C8 C 0.5955(2) 0.6925(3) -0.04128(9) 0.0411(6) Uani 1 1 d . . . . .
C9 C 0.6902(2) 0.9719(3) 0.08142(8) 0.0359(6) Uani 1 1 d . . . . .
C10 C 0.6158(2) 0.9118(3) -0.09595(10) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.6599(2) 0.8242(3) 0.08709(9) 0.0435(6) Uani 1 1 d . . . . .
H11 H 0.660867 0.784512 0.117928 0.052 Uiso 1 1 calc R . . . .
C12 C 0.7306(2) 1.0648(3) 0.12417(9) 0.0396(6) Uani 1 1 d . . . . .
C13 C 0.7655(2) 1.4222(3) 0.16616(8) 0.0377(6) Uani 1 1 d . . . . .
C14 C 0.6276(2) 0.7331(3) 0.04684(9) 0.0441(6) Uani 1 1 d . . . . .
H14 H 0.608745 0.633021 0.051107 0.053 Uiso 1 1 calc R . . . .
C15 C 0.6757(2) 1.1534(3) -0.05809(9) 0.0440(6) Uani 1 1 d . . . . .
H15 H 0.669414 1.194598 -0.088863 0.053 Uiso 1 1 calc R . . . .
C16 C 0.6811(2) 0.5996(3) -0.13755(9) 0.0418(6) Uani 1 1 d . . . . .
C17 C 0.8425(2) 1.5073(3) 0.20474(9) 0.0372(6) Uani 1 1 d . . . . .
C18 C 1.0355(3) 1.5780(3) 0.24926(10) 0.0485(7) Uani 1 1 d . . . . .
H18 H 1.122397 1.572497 0.253317 0.058 Uiso 1 1 calc R . . . .
C19 C 0.6618(2) 0.4813(3) -0.17528(8) 0.0371(6) Uani 1 1 d . . . . .
C20 C 0.9725(2) 1.5034(3) 0.21058(9) 0.0435(6) Uani 1 1 d . . . . .
H20 H 1.016195 1.451548 0.188901 0.052 Uiso 1 1 calc R . . . .
C21 C 0.5800(3) 0.4941(3) -0.21657(9) 0.0493(7) Uani 1 1 d . . . . .
H21 H 0.529710 0.578138 -0.222088 0.059 Uiso 1 1 calc R . . . .
C22 C 0.7327(3) 0.3530(3) -0.16874(9) 0.0478(7) Uani 1 1 d . . . . .
H22 H 0.791090 0.342218 -0.141785 0.057 Uiso 1 1 calc R . . . .
C23 C 0.5743(3) 0.3783(3) -0.24985(10) 0.0543(8) Uani 1 1 d . . . . .
H23 H 0.522195 0.389804 -0.278499 0.065 Uiso 1 1 calc R . . . .
C24 C 0.7838(3) 1.5926(3) 0.23653(10) 0.0520(7) Uani 1 1 d . . . . .
H24 H 0.697086 1.601439 0.233102 0.062 Uiso 1 1 calc R . . . .
C25 C 0.7160(3) 0.2421(3) -0.20244(11) 0.0603(8) Uani 1 1 d . . . . .
H25 H 0.761121 0.154234 -0.196644 0.072 Uiso 1 1 calc R . . . .
C26 C 0.8553(3) 1.6649(3) 0.27355(11) 0.0611(8) Uani 1 1 d . . . . .
H26 H 0.814292 1.722557 0.294636 0.073 Uiso 1 1 calc R . . . .
C27 C 1.0249(8) 0.9598(19) 0.1078(4) 0.210(9) Uani 1 1 d . . . . .
H27 H 1.046733 1.008471 0.136913 0.252 Uiso 1 1 calc R . . . .
C28 C 1.0295(6) 1.0367(8) 0.0688(5) 0.196(6) Uani 1 1 d . . . . .
C29 C 1.0010(4) 0.9656(8) 0.0258(2) 0.1019(17) Uani 1 1 d . . . . .
C30 C 0.9700(4) 0.8223(8) 0.0266(2) 0.0949(15) Uani 1 1 d . . . . .
C31 C 0.9670(5) 0.7500(8) 0.0688(3) 0.134(3) Uani 1 1 d . . . . .
H31 H 0.946602 0.649126 0.069077 0.161 Uiso 1 1 calc R . . . .
C32 C 0.9932(9) 0.8235(17) 0.1097(5) 0.210(8) Uani 1 1 d . . . . .
H32 H 0.988471 0.776660 0.139154 0.252 Uiso 1 1 calc R . . . .
C33 C 0.9512(5) 0.8112(13) -0.0303(5) 0.299(7) Uani 1 1 d . . . . .
H33A H 0.866925 0.774282 -0.038861 0.359 Uiso 1 1 calc R . . . .
H33B H 1.007378 0.733579 -0.039001 0.359 Uiso 1 1 calc R . . . .
N1 N 0.9798(2) 1.6569(3) 0.28090(8) 0.0534(6) Uani 1 1 d . . . . .
N2 N 0.8195(2) 1.2946(2) 0.15364(7) 0.0468(6) Uani 1 1 d . . . . .
H2 H 0.887406 1.264086 0.169814 0.056 Uiso 1 1 calc R . . . .
N3 N 0.76541(19) 1.2118(2) 0.11449(7) 0.0418(5) Uani 1 1 d . . . . .
N4 N 0.58688(19) 0.7632(2) -0.08685(7) 0.0420(5) Uani 1 1 d . . . . .
N5 N 0.5750(2) 0.6669(2) -0.12630(7) 0.0473(6) Uani 1 1 d . . . . .
H5 H 0.503860 0.650796 -0.142738 0.057 Uiso 1 1 calc R . . . .
N6 N 0.6387(2) 0.2522(3) -0.24325(9) 0.0597(7) Uani 1 1 d . . . . .
O1 O 0.66372(16) 1.46651(19) 0.14798(6) 0.0477(5) Uani 1 1 d . . . . .
O2 O 0.8102(2) 1.4020(2) 0.06540(7) 0.0604(6) Uani 1 1 d . . . . .
O3 O 0.73771(19) 1.0195(2) 0.16530(7) 0.0588(6) Uani 1 1 d . . . . .
O4 O 0.6146(2) 0.9572(2) -0.13669(7) 0.0677(6) Uani 1 1 d . . . . .
O5 O 0.5803(2) 0.5590(2) -0.03888(7) 0.0614(6) Uani 1 1 d . . . . .
O6 O 0.78444(18) 0.6337(2) -0.11852(7) 0.0663(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.419(3) . ?
C1 C3 1.409(3) . ?
C1 C9 1.413(3) . ?
C2 C4 1.409(3) . ?
C2 C6 1.417(3) . ?
C3 C5 1.478(3) . ?
C3 C7 1.374(3) . ?
C4 C8 1.479(3) . ?
C4 C14 1.373(3) . ?
C5 N3 1.408(3) . ?
C5 O2 1.206(3) . ?
C6 C10 1.485(3) . ?
C6 C15 1.367(3) . ?
C7 H7 0.9300 . ?
C7 C15 1.396(3) . ?
C8 N4 1.414(3) . ?
C8 O5 1.210(3) . ?
C9 C11 1.376(3) . ?
C9 C12 1.480(3) . ?
C10 N4 1.397(3) . ?
C10 O4 1.206(3) . ?
C11 H11 0.9300 . ?
C11 C14 1.401(3) . ?
C12 N3 1.403(3) . ?
C12 O3 1.212(3) . ?
C13 C17 1.493(3) . ?
C13 N2 1.346(3) . ?
C13 O1 1.221(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C19 1.492(3) . ?
C16 N5 1.357(3) . ?
C16 O6 1.217(3) . ?
C17 C20 1.390(3) . ?
C17 C24 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C20 1.382(3) . ?
C18 N1 1.324(3) . ?
C19 C21 1.375(3) . ?
C19 C22 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C23 1.389(4) . ?
C22 H22 0.9300 . ?
C22 C25 1.366(4) . ?
C23 H23 0.9300 . ?
C23 N6 1.327(4) . ?
C24 H24 0.9300 . ?
C24 C26 1.379(4) . ?
C25 H25 0.9300 . ?
C25 N6 1.337(3) . ?
C26 H26 0.9300 . ?
C26 N1 1.334(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.293(13) . ?
C27 C32 1.270(16) . ?
C28 C29 1.363(12) . ?
C28 C33 1.762(17) 3_775 ?
C29 C29 1.562(10) 3_775 ?
C29 C30 1.327(7) . ?
C30 C31 1.347(7) . ?
C30 C33 1.580(12) . ?
C31 H31 0.9300 . ?
C31 C32 1.321(12) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
N2 H2 0.8600 . ?
N2 N3 1.393(3) . ?
N4 N5 1.393(3) . ?
N5 H5 0.8600 . ?

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
C3 C1 C2 119.0(2) . . ?
C3 C1 C9 121.9(2) . . ?
C9 C1 C2 119.0(2) . . ?
C4 C2 C1 119.3(2) . . ?
C4 C2 C6 122.0(2) . . ?
C6 C2 C1 118.7(2) . . ?
C1 C3 C5 120.1(2) . . ?
C7 C3 C1 120.9(2) . . ?
C7 C3 C5 118.8(2) . . ?
C2 C4 C8 119.4(2) . . ?
C14 C4 C2 120.4(2) . . ?
C14 C4 C8 120.1(2) . . ?
N3 C5 C3 115.2(2) . . ?
O2 C5 C3 124.4(2) . . ?
O2 C5 N3 120.4(2) . . ?
C2 C6 C10 120.1(2) . . ?
C15 C6 C2 120.5(2) . . ?
C15 C6 C10 119.4(2) . . ?
C3 C7 H7 120.1 . . ?
C3 C7 C15 119.8(2) . . ?
C15 C7 H7 120.1 . . ?
N4 C8 C4 116.0(2) . . ?
O5 C8 C4 124.2(2) . . ?
O5 C8 N4 119.8(2) . . ?
C1 C9 C12 119.7(2) . . ?
C11 C9 C1 120.2(2) . . ?
C11 C9 C12 120.0(2) . . ?
N4 C10 C6 115.4(2) . . ?
O4 C10 C6 123.6(2) . . ?
O4 C10 N4 120.9(2) . . ?
C9 C11 H11 119.7 . . ?
C9 C11 C14 120.6(2) . . ?
C14 C11 H11 119.7 . . ?
N3 C12 C9 115.7(2) . . ?
O3 C12 C9 123.8(2) . . ?
O3 C12 N3 120.4(2) . . ?
N2 C13 C17 113.6(2) . . ?
O1 C13 C17 122.3(2) . . ?
O1 C13 N2 124.1(2) . . ?
C4 C14 C11 120.3(2) . . ?
C4 C14 H14 119.8 . . ?
C11 C14 H14 119.8 . . ?
C6 C15 C7 121.0(2) . . ?
C6 C15 H15 119.5 . . ?
C7 C15 H15 119.5 . . ?
N5 C16 C19 115.0(2) . . ?
O6 C16 C19 122.4(2) . . ?
O6 C16 N5 122.5(2) . . ?
C20 C17 C13 122.9(2) . . ?
C24 C17 C13 119.4(2) . . ?
C24 C17 C20 117.7(2) . . ?
C20 C18 H18 118.0 . . ?
N1 C18 H18 118.0 . . ?
N1 C18 C20 124.0(3) . . ?
C21 C19 C16 124.0(2) . . ?
C21 C19 C22 118.2(2) . . ?
C22 C19 C16 117.8(2) . . ?
C17 C20 H20 120.7 . . ?
C18 C20 C17 118.7(3) . . ?
C18 C20 H20 120.7 . . ?
C19 C21 H21 120.8 . . ?
C19 C21 C23 118.4(3) . . ?
C23 C21 H21 120.8 . . ?
C19 C22 H22 120.5 . . ?
C25 C22 C19 119.0(3) . . ?
C25 C22 H22 120.5 . . ?
C21 C23 H23 118.0 . . ?
N6 C23 C21 124.0(3) . . ?
N6 C23 H23 118.0 . . ?
C17 C24 H24 120.5 . . ?
C17 C24 C26 119.1(3) . . ?
C26 C24 H24 120.5 . . ?
C22 C25 H25 118.0 . . ?
N6 C25 C22 124.0(3) . . ?
N6 C25 H25 118.0 . . ?
C24 C26 H26 118.1 . . ?
N1 C26 C24 123.9(3) . . ?
N1 C26 H26 118.1 . . ?
C28 C27 H27 117.2 . . ?
C32 C27 H27 117.2 . . ?
C32 C27 C28 125.6(13) . . ?
C27 C28 C29 117.8(9) . . ?
C27 C28 C33 160.6(13) . 3_775 ?
C29 C28 C33 81.6(9) . 3_775 ?
C28 C29 C29 127.2(10) . 3_775 ?
C30 C29 C28 118.0(6) . . ?
C30 C29 C29 114.8(9) . 3_775 ?
C29 C30 C31 120.7(5) . . ?
C29 C30 C33 92.8(8) . . ?
C31 C30 C33 146.5(8) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.4(9) . . ?
C32 C31 H31 120.3 . . ?
C27 C32 C31 118.4(13) . . ?
C27 C32 H32 120.8 . . ?
C31 C32 H32 120.8 . . ?
C28 C33 H33A 106.4 3_775 . ?
C28 C33 H33B 106.4 3_775 . ?
C30 C33 C28 123.6(6) . 3_775 ?
C30 C33 H33A 106.4 . . ?
C30 C33 H33B 106.4 . . ?
H33A C33 H33B 106.5 . . ?
C18 N1 C26 116.5(2) . . ?
C13 N2 H2 120.0 . . ?
C13 N2 N3 120.09(19) . . ?
N3 N2 H2 120.0 . . ?
C12 N3 C5 127.1(2) . . ?
N2 N3 C5 115.8(2) . . ?
N2 N3 C12 116.48(19) . . ?
C10 N4 C8 126.6(2) . . ?
N5 N4 C8 115.1(2) . . ?
N5 N4 C10 116.7(2) . . ?
C16 N5 N4 116.9(2) . . ?
C16 N5 H5 121.6 . . ?
N4 N5 H5 121.6 . . ?
C23 N6 C25 116.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O5 0.93 2.57 3.199(3) 125.3 1_565 yes
C21 H21 N6 0.93 2.50 3.399(4) 162.1 2_654 yes
C33 H33B O2 0.97 2.49 3.427(6) 163.4 3_775 yes
N2 H2 N1 0.86 2.10 2.941(3) 164.8 2_745 yes
N5 H5 O1 0.86 2.08 2.836(3) 146.8 3_675 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C4 C8 -175.7(2) . . . . ?
C1 C2 C4 C14 1.6(3) . . . . ?
C1 C2 C6 C10 177.5(2) . . . . ?
C1 C2 C6 C15 -0.7(3) . . . . ?
C1 C3 C5 N3 -6.6(3) . . . . ?
C1 C3 C5 O2 172.7(2) . . . . ?
C1 C3 C7 C15 -0.4(4) . . . . ?
C1 C9 C11 C14 1.3(4) . . . . ?
C1 C9 C12 N3 -1.2(3) . . . . ?
C1 C9 C12 O3 -179.2(2) . . . . ?
C2 C1 C3 C5 -174.0(2) . . . . ?
C2 C1 C3 C7 2.3(3) . . . . ?
C2 C1 C9 C11 0.0(3) . . . . ?
C2 C1 C9 C12 178.1(2) . . . . ?
C2 C4 C8 N4 -5.9(3) . . . . ?
C2 C4 C8 O5 174.0(2) . . . . ?
C2 C4 C14 C11 -0.3(4) . . . . ?
C2 C6 C10 N4 2.4(3) . . . . ?
C2 C6 C10 O4 -177.6(3) . . . . ?
C2 C6 C15 C7 2.6(4) . . . . ?
C3 C1 C2 C4 177.0(2) . . . . ?
C3 C1 C2 C6 -1.8(3) . . . . ?
C3 C1 C9 C11 -178.4(2) . . . . ?
C3 C1 C9 C12 -0.3(3) . . . . ?
C3 C5 N3 C12 5.4(4) . . . . ?
C3 C5 N3 N2 175.5(2) . . . . ?
C3 C7 C15 C6 -2.1(4) . . . . ?
C4 C2 C6 C10 -1.3(4) . . . . ?
C4 C2 C6 C15 -179.4(2) . . . . ?
C4 C8 N4 C10 7.8(4) . . . . ?
C4 C8 N4 N5 172.8(2) . . . . ?
C5 C3 C7 C15 176.0(2) . . . . ?
C6 C2 C4 C8 3.1(3) . . . . ?
C6 C2 C4 C14 -179.6(2) . . . . ?
C6 C10 N4 C8 -6.1(4) . . . . ?
C6 C10 N4 N5 -170.9(2) . . . . ?
C7 C3 C5 N3 177.0(2) . . . . ?
C7 C3 C5 O2 -3.8(4) . . . . ?
C8 C4 C14 C11 176.9(2) . . . . ?
C8 N4 N5 C16 -78.9(3) . . . . ?
C9 C1 C2 C4 -1.4(3) . . . . ?
C9 C1 C2 C6 179.8(2) . . . . ?
C9 C1 C3 C5 4.4(3) . . . . ?
C9 C1 C3 C7 -179.3(2) . . . . ?
C9 C11 C14 C4 -1.2(4) . . . . ?
C9 C12 N3 C5 -1.7(4) . . . . ?
C9 C12 N3 N2 -171.7(2) . . . . ?
C10 C6 C15 C7 -175.5(2) . . . . ?
C10 N4 N5 C16 87.7(3) . . . . ?
C11 C9 C12 N3 177.0(2) . . . . ?
C11 C9 C12 O3 -1.1(4) . . . . ?
C12 C9 C11 C14 -176.8(2) . . . . ?
C13 C17 C20 C18 -175.8(2) . . . . ?
C13 C17 C24 C26 176.8(3) . . . . ?
C13 N2 N3 C5 68.4(3) . . . . ?
C13 N2 N3 C12 -120.4(3) . . . . ?
C14 C4 C8 N4 176.8(2) . . . . ?
C14 C4 C8 O5 -3.3(4) . . . . ?
C15 C6 C10 N4 -179.4(2) . . . . ?
C15 C6 C10 O4 0.5(4) . . . . ?
C16 C19 C21 C23 177.4(2) . . . . ?
C16 C19 C22 C25 179.3(2) . . . . ?
C17 C13 N2 N3 -172.8(2) . . . . ?
C17 C24 C26 N1 -0.4(5) . . . . ?
C19 C16 N5 N4 171.6(2) . . . . ?
C19 C21 C23 N6 3.4(4) . . . . ?
C19 C22 C25 N6 3.5(5) . . . . ?
C20 C17 C24 C26 -2.6(4) . . . . ?
C20 C18 N1 C26 -1.2(4) . . . . ?
C21 C19 C22 C25 -2.3(4) . . . . ?
C21 C23 N6 C25 -2.4(4) . . . . ?
C22 C19 C21 C23 -0.9(4) . . . . ?
C22 C25 N6 C23 -1.1(4) . . . . ?
C24 C17 C20 C18 3.5(4) . . . . ?
C24 C26 N1 C18 2.3(4) . . . . ?
C27 C28 C29 C29 179.5(6) . . . 3_775 ?
C27 C28 C29 C30 0.2(9) . . . . ?
C28 C27 C32 C31 2.9(18) . . . . ?
C28 C29 C30 C31 0.0(7) . . . . ?
C28 C29 C30 C33 -179.7(5) . . . . ?
C29 C29 C30 C31 -179.4(4) 3_775 . . . ?
C29 C29 C30 C33 0.9(5) 3_775 . . . ?
C29 C30 C31 C32 1.1(9) . . . . ?
C29 C30 C33 C28 -1.1(5) . . . 3_775 ?
C30 C31 C32 C27 -2.5(14) . . . . ?
C31 C30 C33 C28 179.3(6) . . . 3_775 ?
C32 C27 C28 C29 -1.8(15) . . . . ?
C32 C27 C28 C33 176.7(16) . . . 3_775 ?
C33 C28 C29 C29 0.0(7) 3_775 . . 3_775 ?
C33 C28 C29 C30 -179.3(4) 3_775 . . . ?
C33 C30 C31 C32 -179.3(7) . . . . ?
N1 C18 C20 C17 -1.7(4) . . . . ?
N2 C13 C17 C20 30.2(3) . . . . ?
N2 C13 C17 C24 -149.0(2) . . . . ?
N5 C16 C19 C21 42.3(4) . . . . ?
N5 C16 C19 C22 -139.4(2) . . . . ?
O1 C13 C17 C20 -149.4(3) . . . . ?
O1 C13 C17 C24 31.3(4) . . . . ?
O1 C13 N2 N3 6.8(4) . . . . ?
O2 C5 N3 C12 -173.9(2) . . . . ?
O2 C5 N3 N2 -3.8(4) . . . . ?
O3 C12 N3 C5 176.4(2) . . . . ?
O3 C12 N3 N2 6.4(4) . . . . ?
O4 C10 N4 C8 174.0(2) . . . . ?
O4 C10 N4 N5 9.2(4) . . . . ?
O5 C8 N4 C10 -172.1(2) . . . . ?
O5 C8 N4 N5 -7.1(3) . . . . ?
O6 C16 C19 C21 -137.3(3) . . . . ?
O6 C16 C19 C22 41.1(4) . . . . ?
O6 C16 N5 N4 -8.9(4) . . . . ?

_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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2059474'
loop_
_audit_author_name
_audit_author_address
'Chen Wang'
;College of Chemistry and Chemical Engineering, Liaoning Normal University
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H3 I3 O6, C5 H4 N'
_chemical_formula_sum            'C14 H7 I3 N O6'
_chemical_formula_weight         665.91
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.9598(5)
_cell_length_b                   21.9155(11)
_cell_length_c                   9.5862(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.7110(10)
_cell_angle_gamma                90
_cell_volume                     1681.46(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6900
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.893
_cell_measurement_theta_min      2.554
_shelx_estimated_absorpt_T_max   0.231
_shelx_estimated_absorpt_T_min   0.104
_exptl_absorpt_coefficient_mu    5.607
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1173 before and 0.0333 after correction.
The Ratio of minimum to maximum transmission is 0.6500.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.37
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.113
_diffrn_reflns_theta_min         1.858
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4332
_reflns_number_total             4822
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.153
_refine_diff_density_min         -2.001
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.076
_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)+(0.0315P)²+7.5243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C11(H11), C10(H10)
2.b Tetrahedral OH refined with riding coordinates:
 O3(H3), O5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I3 I 0.18453(4) 0.55122(2) 0.49885(3) 0.03009(8) Uani 1 1 d . . . . .
I1 I 0.66567(4) 0.74537(2) 0.90978(4) 0.03571(9) Uani 1 1 d . . . . .
I2 I 0.08800(5) 0.66644(2) 1.02395(4) 0.04309(10) Uani 1 1 d . . . . .
O3 O -0.1197(4) 0.60393(13) 0.6455(4) 0.0260(6) Uani 1 1 d . . . . .
H3 H -0.185248 0.578911 0.585619 0.039 Uiso 1 1 calc R . . . .
O6 O 0.4946(4) 0.66030(15) 0.5297(4) 0.0323(7) Uani 1 1 d . . . . .
O2 O 0.3442(4) 0.79872(15) 0.9929(4) 0.0345(7) Uani 1 1 d . . . . .
H2 H 0.377826 0.824961 1.061194 0.052 Uiso 1 1 calc GR . . . .
O5 O 0.6472(4) 0.59947(16) 0.7299(4) 0.0367(8) Uani 1 1 d . . . . .
H5 H 0.635166 0.584231 0.802304 0.055 Uiso 1 1 calc R . . . .
O4 O 0.0326(4) 0.52611(14) 0.7891(4) 0.0345(7) Uani 1 1 d . . . . .
O1 O 0.4869(6) 0.73574(17) 1.1908(4) 0.0516(11) Uani 1 1 d . . . . .
C5 C 0.2689(5) 0.61034(17) 0.6923(4) 0.0191(7) Uani 1 1 d . . . . .
C4 C 0.1738(5) 0.61567(17) 0.7737(4) 0.0194(7) Uani 1 1 d . . . . .
C3 C 0.2238(5) 0.65857(18) 0.8952(5) 0.0223(7) Uani 1 1 d . . . . .
C9 C 0.0180(5) 0.57735(17) 0.7341(5) 0.0207(7) Uani 1 1 d . . . . .
C1 C 0.4555(5) 0.68925(17) 0.8514(4) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.3603(5) 0.69668(17) 0.9313(5) 0.0221(7) Uani 1 1 d . . . . .
C8 C 0.4044(5) 0.74552(18) 1.0550(5) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.5223(5) 0.63618(17) 0.6515(5) 0.0218(7) Uani 1 1 d . . . . .
C6 C 0.4132(5) 0.64528(17) 0.7334(4) 0.0197(7) Uani 1 1 d . . . . .
N1 N 0.5792(7) 0.6099(2) 0.2887(5) 0.0452(11) Uani 1 1 d . . . . .
C12 C 0.5172(6) 0.52328(19) 0.0625(5) 0.0322(10) Uani 1 1 d . . . . .
C13 C 0.6545(7) 0.5627(3) 0.1096(7) 0.0467(13) Uani 1 1 d . . . . .
H13 H 0.727197 0.559753 0.064823 0.056 Uiso 1 1 calc R . . . .
C14 C 0.6808(8) 0.6059(3) 0.2229(8) 0.0545(16) Uani 1 1 d . . . . .
H14 H 0.770984 0.632422 0.253366 0.065 Uiso 1 1 calc R . . . .
C11 C 0.4132(9) 0.5292(3) 0.1337(7) 0.0471(13) Uani 1 1 d . . . . .
H11 H 0.320166 0.504124 0.104315 0.057 Uiso 1 1 calc R . . . .
C10 C 0.4494(9) 0.5729(3) 0.2494(7) 0.0511(15) Uani 1 1 d . . . . .
H10 H 0.381997 0.576156 0.299744 0.061 Uiso 1 1 calc R . . . .


_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
I3 C5 2.105(4) . ?
I1 C1 2.103(4) . ?
I2 C3 2.094(4) . ?
O3 H3 0.8200 . ?
O3 C9 1.281(5) . ?
O6 C7 1.201(5) . ?
O2 H2 0.8200 . ?
O2 C8 1.310(5) . ?
O5 H5 0.8200 . ?
O5 C7 1.306(5) . ?
O4 C9 1.223(5) . ?
O1 C8 1.192(6) . ?
C5 C4 1.395(5) . ?
C5 C6 1.399(5) . ?
C4 C3 1.404(5) . ?
C4 C9 1.523(5) . ?
C3 C2 1.390(6) . ?
C1 C2 1.388(6) . ?
C1 C6 1.403(5) . ?
C2 C8 1.512(5) . ?
C7 C6 1.516(5) . ?
N1 C14 1.323(9) . ?
N1 C10 1.327(9) . ?
C12 C12 1.497(8) 3_665 ?
C12 C13 1.402(8) . ?
C12 C11 1.386(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(8) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.388(8) . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 H3 109.5 . . ?
C8 O2 H2 109.5 . . ?
C7 O5 H5 109.5 . . ?
C4 C5 I3 118.5(3) . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 I3 120.3(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C9 122.4(3) . . ?
C3 C4 C9 119.4(3) . . ?
C4 C3 I2 119.4(3) . . ?
C2 C3 I2 118.9(3) . . ?
C2 C3 C4 121.7(4) . . ?
O3 C9 C4 114.6(3) . . ?
O4 C9 O3 126.0(4) . . ?
O4 C9 C4 119.4(4) . . ?
C2 C1 I1 118.9(3) . . ?
C2 C1 C6 121.0(3) . . ?
C6 C1 I1 120.1(3) . . ?
C3 C2 C8 120.7(4) . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 C8 120.5(4) . . ?
O2 C8 C2 111.4(4) . . ?
O1 C8 O2 125.6(4) . . ?
O1 C8 C2 122.9(4) . . ?
O6 C7 O5 125.4(4) . . ?
O6 C7 C6 123.0(4) . . ?
O5 C7 C6 111.6(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 120.8(3) . . ?
C1 C6 C7 120.3(3) . . ?
C14 N1 C10 121.7(5) . . ?
C13 C12 C12 120.9(6) . 3_665 ?
C11 C12 C12 121.1(6) . 3_665 ?
C11 C12 C13 118.1(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 120.7(6) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
N1 C10 C11 120.6(6) . . ?
N1 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?

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
O2 H2 O3 0.82 1.75 2.524(4) 156.4 4_676 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I3 C5 C4 C3 -175.3(3) . . . . ?
I3 C5 C4 C9 4.0(5) . . . . ?
I3 C5 C6 C1 172.8(3) . . . . ?
I3 C5 C6 C7 -7.0(5) . . . . ?
I1 C1 C2 C3 -178.5(3) . . . . ?
I1 C1 C2 C8 1.7(5) . . . . ?
I1 C1 C6 C5 -177.3(3) . . . . ?
I1 C1 C6 C7 2.4(5) . . . . ?
I2 C3 C2 C1 176.7(3) . . . . ?
I2 C3 C2 C8 -3.5(5) . . . . ?
O6 C7 C6 C5 84.2(5) . . . . ?
O6 C7 C6 C1 -95.5(5) . . . . ?
O5 C7 C6 C5 -95.8(4) . . . . ?
O5 C7 C6 C1 84.5(4) . . . . ?
C5 C4 C3 I2 -178.5(3) . . . . ?
C5 C4 C3 C2 2.4(6) . . . . ?
C5 C4 C9 O3 -97.0(4) . . . . ?
C5 C4 C9 O4 84.4(5) . . . . ?
C4 C5 C6 C1 -4.4(6) . . . . ?
C4 C5 C6 C7 175.8(4) . . . . ?
C4 C3 C2 C1 -4.2(6) . . . . ?
C4 C3 C2 C8 175.6(4) . . . . ?
C3 C4 C9 O3 82.3(5) . . . . ?
C3 C4 C9 O4 -96.3(5) . . . . ?
C3 C2 C8 O2 -97.1(5) . . . . ?
C3 C2 C8 O1 84.5(6) . . . . ?
C9 C4 C3 I2 2.2(5) . . . . ?
C9 C4 C3 C2 -176.9(4) . . . . ?
C1 C2 C8 O2 82.7(5) . . . . ?
C1 C2 C8 O1 -95.7(6) . . . . ?
C2 C1 C6 C5 2.6(6) . . . . ?
C2 C1 C6 C7 -177.7(4) . . . . ?
C6 C5 C4 C3 2.0(6) . . . . ?
C6 C5 C4 C9 -178.7(3) . . . . ?
C6 C1 C2 C3 1.7(6) . . . . ?
C6 C1 C2 C8 -178.2(4) . . . . ?
C12 C12 C13 C14 178.8(6) 3_665 . . . ?
C12 C12 C11 C10 179.9(5) 3_665 . . . ?
C12 C13 C14 N1 0.8(9) . . . . ?
C12 C11 C10 N1 2.0(9) . . . . ?
C13 C12 C11 C10 -0.8(8) . . . . ?
C14 N1 C10 C11 -1.7(9) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C10 N1 C14 C13 0.3(9) . . . . ?

_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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2059473'
loop_
_audit_author_name
_audit_author_address
'Chen Wang'
;College of Chemistry and Chemical Engineering, Liaoning Normal University
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H4 I2 O6, C5 H4 N'
_chemical_formula_sum            'C14 H8 I2 N O6'
_chemical_formula_weight         540.01
_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'
I I -0.4742 1.8119 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.811(6)
_cell_length_b                   9.023(4)
_cell_length_c                   24.110(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.673(7)
_cell_angle_gamma                90
_cell_volume                     3086(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.088
_cell_measurement_theta_min      2.675
_shelx_estimated_absorpt_T_max   0.328
_shelx_estimated_absorpt_T_min   0.124
_exptl_absorpt_coefficient_mu    4.106
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.8682.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.609
_diffrn_reflns_theta_min         2.675
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3827
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.030
_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)+(0.0356P)²+9.8609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0891
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C11(H11), C10(H10), C14(H14)
2.b Tetrahedral OH refined with riding coordinates:
 O4(H4), O1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.64387(3) 0.34146(5) 0.03894(2) 0.04945(13) Uani 1 1 d . . . . .
I2 I 0.63593(3) 0.69487(5) 0.24810(2) 0.05828(14) Uani 1 1 d . . . . .
O3 O 0.5125(2) 0.4320(4) 0.14741(15) 0.0449(9) Uani 1 1 d . . . . .
O4 O 0.5212(2) 0.6251(4) 0.09296(14) 0.0463(9) Uani 1 1 d . . . . .
H4 H 0.496289 0.589972 0.060836 0.069 Uiso 1 1 calc R . . . .
O1 O 0.9030(3) 0.7934(4) 0.26492(15) 0.0505(10) Uani 1 1 d . . . . .
H1 H 0.919408 0.789519 0.235215 0.076 Uiso 1 1 calc R . . . .
O5 O 0.8796(3) 0.2420(4) 0.11288(17) 0.0539(10) Uani 1 1 d . . . . .
H5 H 0.926260 0.208229 0.105485 0.081 Uiso 1 1 calc GR . . . .
C6 C 0.7111(3) 0.5927(5) 0.19783(17) 0.0294(9) Uani 1 1 d . . . . .
O6 O 0.9119(3) 0.4421(5) 0.0711(2) 0.0770(15) Uani 1 1 d . . . . .
C5 C 0.6630(3) 0.5215(5) 0.14710(17) 0.0281(9) Uani 1 1 d . . . . .
C3 C 0.8119(3) 0.4593(5) 0.13152(17) 0.0277(9) Uani 1 1 d . . . . .
O2 O 0.8668(4) 0.6191(5) 0.31708(16) 0.0848(17) Uani 1 1 d . . . . .
N1 N 0.7988(4) 0.4400(5) 0.3863(2) 0.0523(12) Uani 1 1 d . . . . .
C12 C 0.7611(3) 0.2891(5) 0.47590(19) 0.0341(10) Uani 1 1 d . . . . .
C9 C 0.5567(3) 0.5239(6) 0.12715(18) 0.0329(10) Uani 1 1 d . . . . .
C8 C 0.8729(3) 0.3811(6) 0.10120(19) 0.0362(11) Uani 1 1 d . . . . .
C4 C 0.7150(3) 0.4524(5) 0.11508(16) 0.0284(9) Uani 1 1 d . . . . .
C2 C 0.8576(3) 0.5390(5) 0.18060(18) 0.0309(10) Uani 1 1 d . . . . .
H2 H 0.922710 0.549967 0.190590 0.037 Uiso 1 1 calc R . . . .
C1 C 0.8078(3) 0.6026(5) 0.21497(18) 0.0321(10) Uani 1 1 d . . . . .
C7 C 0.8623(4) 0.6730(5) 0.2710(2) 0.0390(11) Uani 1 1 d . . . . .
C13 C 0.8513(4) 0.3182(7) 0.4758(3) 0.0540(15) Uani 1 1 d . . . . .
H13 H 0.901297 0.286320 0.506514 0.065 Uiso 1 1 calc R . . . .
C11 C 0.6896(4) 0.3375(7) 0.4292(2) 0.0546(15) Uani 1 1 d . . . . .
H11 H 0.627090 0.320204 0.427681 0.066 Uiso 1 1 calc R . . . .
C10 C 0.7111(5) 0.4118(8) 0.3846(3) 0.0659(18) Uani 1 1 d . . . . .
H10 H 0.662552 0.442309 0.352716 0.079 Uiso 1 1 calc R . . . .
C14 C 0.8688(5) 0.3946(8) 0.4305(3) 0.0605(16) Uani 1 1 d . . . . .
H14 H 0.930624 0.414454 0.431068 0.073 Uiso 1 1 calc R . . . .


_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
I1 C4 2.091(4) . ?
I2 C6 2.081(4) . ?
O3 C9 1.240(6) . ?
O4 H4 0.8200 . ?
O4 C9 1.241(5) . ?
O1 H1 0.8200 . ?
O1 C7 1.271(6) . ?
O5 H5 0.8200 . ?
O5 C8 1.284(7) . ?
C6 C5 1.384(6) . ?
C6 C1 1.375(6) . ?
O6 C8 1.184(6) . ?
C5 C9 1.509(6) . ?
C5 C4 1.385(6) . ?
C3 C8 1.492(6) . ?
C3 C4 1.376(6) . ?
C3 C2 1.384(6) . ?
O2 C7 1.197(6) . ?
N1 C10 1.313(8) . ?
N1 C14 1.321(8) . ?
C12 C12 1.475(9) 7_656 ?
C12 C13 1.362(7) . ?
C12 C11 1.377(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.382(6) . ?
C1 C7 1.501(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(8) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O4 H4 109.5 . . ?
C7 O1 H1 109.5 . . ?
C8 O5 H5 109.5 . . ?
C5 C6 I2 119.7(3) . . ?
C1 C6 I2 118.8(3) . . ?
C1 C6 C5 121.5(4) . . ?
C6 C5 C9 120.0(4) . . ?
C6 C5 C4 118.3(4) . . ?
C4 C5 C9 121.7(4) . . ?
C4 C3 C8 124.4(4) . . ?
C4 C3 C2 118.9(4) . . ?
C2 C3 C8 116.6(4) . . ?
C10 N1 C14 120.4(5) . . ?
C13 C12 C12 122.2(5) . 7_656 ?
C13 C12 C11 117.5(5) . . ?
C11 C12 C12 120.3(6) . 7_656 ?
O3 C9 O4 125.7(4) . . ?
O3 C9 C5 119.0(4) . . ?
O4 C9 C5 115.2(4) . . ?
O5 C8 C3 112.0(4) . . ?
O6 C8 O5 124.6(5) . . ?
O6 C8 C3 123.4(5) . . ?
C5 C4 I1 118.9(3) . . ?
C3 C4 I1 119.7(3) . . ?
C3 C4 C5 121.3(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 C3 120.9(4) . . ?
C1 C2 H2 119.5 . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 C7 122.9(4) . . ?
C2 C1 C7 118.3(4) . . ?
O1 C7 C1 114.1(4) . . ?
O2 C7 O1 123.5(5) . . ?
O2 C7 C1 122.4(5) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(6) . . ?
C10 C11 H11 120.1 . . ?
N1 C10 C11 121.1(6) . . ?
N1 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
N1 C14 C13 120.8(6) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O4 0.82 1.70 2.514(5) 175.2 3_545 yes
C14 H14 O6 0.93 2.36 3.288(7) 174.6 2_755 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I2 C6 C5 C9 2.7(6) . . . . ?
I2 C6 C5 C4 -179.0(3) . . . . ?
I2 C6 C1 C2 -177.9(3) . . . . ?
I2 C6 C1 C7 5.2(6) . . . . ?
C6 C5 C9 O3 -83.6(6) . . . . ?
C6 C5 C9 O4 93.3(5) . . . . ?
C6 C5 C4 I1 179.1(3) . . . . ?
C6 C5 C4 C3 -2.8(6) . . . . ?
C6 C1 C7 O1 -112.0(5) . . . . ?
C6 C1 C7 O2 68.3(8) . . . . ?
C5 C6 C1 C2 -0.3(7) . . . . ?
C5 C6 C1 C7 -177.2(4) . . . . ?
C3 C2 C1 C6 -3.7(7) . . . . ?
C3 C2 C1 C7 173.3(4) . . . . ?
C12 C12 C13 C14 -178.5(6) 7_656 . . . ?
C12 C12 C11 C10 179.4(6) 7_656 . . . ?
C12 C13 C14 N1 -0.5(10) . . . . ?
C12 C11 C10 N1 -1.4(10) . . . . ?
C9 C5 C4 I1 -2.6(6) . . . . ?
C9 C5 C4 C3 175.5(4) . . . . ?
C8 C3 C4 I1 -5.5(6) . . . . ?
C8 C3 C4 C5 176.4(4) . . . . ?
C8 C3 C2 C1 -173.3(4) . . . . ?
C4 C5 C9 O3 98.1(5) . . . . ?
C4 C5 C9 O4 -85.0(5) . . . . ?
C4 C3 C8 O5 -76.1(6) . . . . ?
C4 C3 C8 O6 105.6(6) . . . . ?
C4 C3 C2 C1 4.4(7) . . . . ?
C2 C3 C8 O5 101.4(5) . . . . ?
C2 C3 C8 O6 -76.9(6) . . . . ?
C2 C3 C4 I1 177.1(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C1 C7 O1 71.1(6) . . . . ?
C2 C1 C7 O2 -108.6(6) . . . . ?
C1 C6 C5 C9 -174.9(4) . . . . ?
C1 C6 C5 C4 3.5(7) . . . . ?
C13 C12 C11 C10 0.3(9) . . . . ?
C11 C12 C13 C14 0.6(9) . . . . ?
C10 N1 C14 C13 -0.6(10) . . . . ?
C14 N1 C10 C11 1.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
