# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_161126h
_audit_block_doi                 10.5517/ccdc.csd.cc1ngbwb
_database_code_depnum_ccdc_archive 'CCDC 1533132'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H15 Cl N12 O5'
_chemical_formula_weight         406.78

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   9.5165(9)
_cell_length_b                   8.7913(8)
_cell_length_c                   20.3743(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1704.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8942
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8072
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3011
_reflns_number_gt                1824
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.08092(14) 0.27495(12) 0.90047(7) 0.0594(4) Uani 1 1 d . . .
N1 N 0.8320(4) 0.2411(4) 0.72507(19) 0.0489(10) Uani 1 1 d . . .
N2 N 0.9186(4) 0.1740(4) 0.68516(18) 0.0478(10) Uani 1 1 d . . .
N3 N 1.0246(4) 0.4093(4) 0.6602(2) 0.0527(10) Uani 1 1 d . . .
N4 N 0.9366(4) 0.4793(4) 0.7008(2) 0.0491(10) Uani 1 1 d . . .
N5 N 1.1037(4) 0.1848(4) 0.61223(19) 0.0475(10) Uani 1 1 d . . .
N6 N 1.1115(4) 0.0287(4) 0.6172(2) 0.0520(10) Uani 1 1 d . . .
N7 N 0.7563(4) 0.4534(4) 0.7764(2) 0.0577(11) Uani 1 1 d . . .
H7 H 0.7093 0.3945 0.8020 0.069 Uiso 1 1 calc R . .
N8 N 0.7400(4) 0.6096(4) 0.7810(2) 0.0549(11) Uani 1 1 d . . .
H8 H 0.6824 0.6574 0.7558 0.066 Uiso 1 1 calc R . .
N9 N 0.9008(4) 0.6295(4) 0.8701(2) 0.0605(11) Uani 1 1 d . . .
H9 H 0.9142 0.5342 0.8773 0.073 Uiso 1 1 calc R . .
N10 N 0.9660(4) 0.7438(5) 0.9043(3) 0.0729(12) Uani 1 1 d . . .
N11 N 0.8212(4) 0.8353(4) 0.83030(19) 0.0515(11) Uani 1 1 d . . .
N12 N 0.7487(5) 0.9273(4) 0.7862(2) 0.0665(12) Uani 1 1 d . . .
H12B H 0.7286 1.0152 0.8057 0.100 Uiso 1 1 d R . .
H12C H 0.8026 0.9444 0.7513 0.100 Uiso 1 1 d R . .
O1 O 0.0424(5) 0.2485(5) 0.8343(2) 0.1052(15) Uani 1 1 d . . .
O2 O 0.1993(5) 0.3710(5) 0.9034(3) 0.1179(17) Uani 1 1 d . . .
O3 O 0.1087(5) 0.1369(4) 0.9317(2) 0.1007(17) Uani 1 1 d . . .
O4 O -0.0275(6) 0.3521(5) 0.9311(2) 0.1137(18) Uani 1 1 d . . .
O5 O 0.0052(4) 0.8174(3) 0.71025(17) 0.0615(9) Uani 1 1 d . . .
H5C H -0.0081 0.7251 0.6996 0.074 Uiso 1 1 d R . .
H5D H 0.0368 0.8652 0.6771 0.074 Uiso 1 1 d R . .
C1 C 1.0134(5) 0.2595(5) 0.6537(2) 0.0405(10) Uani 1 1 d . . .
C2 C 0.8456(5) 0.3933(5) 0.7321(2) 0.0423(11) Uani 1 1 d . . .
C3 C 1.2079(6) -0.0104(6) 0.5738(2) 0.0577(14) Uani 1 1 d . . .
C4 C 1.2612(6) 0.1165(6) 0.5405(2) 0.0593(14) Uani 1 1 d . . .
H4 H 1.3295 0.1161 0.5078 0.071 Uiso 1 1 calc R . .
C5 C 1.1944(5) 0.2389(5) 0.5648(2) 0.0521(13) Uani 1 1 d . . .
C6 C 1.2452(8) -0.1751(6) 0.5665(3) 0.0830(19) Uani 1 1 d . . .
H6A H 1.2004 -0.2154 0.5280 0.124 Uiso 1 1 calc R . .
H6B H 1.2139 -0.2302 0.6044 0.124 Uiso 1 1 calc R . .
H6C H 1.3453 -0.1852 0.5622 0.124 Uiso 1 1 calc R . .
C7 C 1.2128(6) 0.4038(6) 0.5470(3) 0.0730(17) Uani 1 1 d . . .
H7A H 1.2787 0.4124 0.5115 0.110 Uiso 1 1 calc R . .
H7B H 1.2474 0.4587 0.5844 0.110 Uiso 1 1 calc R . .
H7C H 1.1240 0.4455 0.5337 0.110 Uiso 1 1 calc R . .
C8 C 0.8157(5) 0.6831(5) 0.8251(2) 0.0456(12) Uani 1 1 d . . .
C9 C 0.9164(6) 0.8653(6) 0.8793(3) 0.0657(16) Uani 1 1 d . . .
H9A H 0.9417 0.9628 0.8926 0.079 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
Cl1 O4 1.383(4) . ?
Cl1 O3 1.396(4) . ?
Cl1 O2 1.409(4) . ?
Cl1 O1 1.417(4) . ?
N1 N2 1.299(5) . ?
N1 C2 1.351(5) . ?
N2 C1 1.338(6) . ?
N3 N4 1.328(5) . ?
N3 C1 1.328(5) . ?
N4 C2 1.314(5) . ?
N5 C1 1.372(6) . ?
N5 N6 1.378(4) . ?
N5 C5 1.380(6) . ?
N6 C3 1.319(6) . ?
N7 C2 1.348(6) . ?
N7 N8 1.386(5) . ?
N7 H7 0.8600 . ?
N8 C8 1.320(6) . ?
N8 H8 0.8600 . ?
N9 C8 1.311(6) . ?
N9 N10 1.371(5) . ?
N9 H9 0.8600 . ?
N10 C9 1.274(6) . ?
N11 C8 1.343(5) . ?
N11 C9 1.374(6) . ?
N11 N12 1.391(5) . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8899 . ?
O5 H5C 0.8500 . ?
O5 H5D 0.8499 . ?
C3 C4 1.401(7) . ?
C3 C6 1.499(7) . ?
C4 C5 1.344(7) . ?
C4 H4 0.9300 . ?
C5 C7 1.504(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 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
O4 Cl1 O3 111.2(3) . . ?
O4 Cl1 O2 106.5(3) . . ?
O3 Cl1 O2 110.5(3) . . ?
O4 Cl1 O1 108.4(3) . . ?
O3 Cl1 O1 109.9(3) . . ?
O2 Cl1 O1 110.2(3) . . ?
N2 N1 C2 117.0(4) . . ?
N1 N2 C1 118.2(4) . . ?
N4 N3 C1 118.2(4) . . ?
C2 N4 N3 116.8(4) . . ?
C1 N5 N6 117.7(4) . . ?
C1 N5 C5 131.1(4) . . ?
N6 N5 C5 111.1(4) . . ?
C3 N6 N5 104.4(4) . . ?
C2 N7 N8 120.3(4) . . ?
C2 N7 H7 119.9 . . ?
N8 N7 H7 119.9 . . ?
C8 N8 N7 118.0(4) . . ?
C8 N8 H8 121.0 . . ?
N7 N8 H8 121.0 . . ?
C8 N9 N10 111.8(4) . . ?
C8 N9 H9 124.1 . . ?
N10 N9 H9 124.1 . . ?
C9 N10 N9 104.1(5) . . ?
C8 N11 C9 105.9(4) . . ?
C8 N11 N12 120.6(4) . . ?
C9 N11 N12 133.2(4) . . ?
N11 N12 H12B 108.9 . . ?
N11 N12 H12C 109.2 . . ?
H12B N12 H12C 109.5 . . ?
H5C O5 H5D 108.8 . . ?
N3 C1 N2 124.2(4) . . ?
N3 C1 N5 119.1(4) . . ?
N2 C1 N5 116.7(4) . . ?
N4 C2 N7 121.0(4) . . ?
N4 C2 N1 125.6(4) . . ?
N7 C2 N1 113.5(4) . . ?
N6 C3 C4 111.7(5) . . ?
N6 C3 C6 118.9(5) . . ?
C4 C3 C6 129.4(6) . . ?
C5 C4 C3 106.7(5) . . ?
C5 C4 H4 126.7 . . ?
C3 C4 H4 126.7 . . ?
C4 C5 N5 106.2(4) . . ?
C4 C5 C7 128.8(5) . . ?
N5 C5 C7 125.0(4) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N9 C8 N8 129.6(4) . . ?
N9 C8 N11 106.2(4) . . ?
N8 C8 N11 124.2(4) . . ?
N10 C9 N11 111.9(4) . . ?
N10 C9 H9A 124.0 . . ?
N11 C9 H9A 124.0 . . ?

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
C2 N1 N2 C1 -0.6(6) . . . . ?
C1 N3 N4 C2 0.7(6) . . . . ?
C1 N5 N6 C3 -178.0(4) . . . . ?
C5 N5 N6 C3 1.0(5) . . . . ?
C2 N7 N8 C8 -95.1(5) . . . . ?
C8 N9 N10 C9 0.8(6) . . . . ?
N4 N3 C1 N2 0.3(7) . . . . ?
N4 N3 C1 N5 -179.7(4) . . . . ?
N1 N2 C1 N3 -0.4(7) . . . . ?
N1 N2 C1 N5 179.6(4) . . . . ?
N6 N5 C1 N3 165.7(4) . . . . ?
C5 N5 C1 N3 -13.1(7) . . . . ?
N6 N5 C1 N2 -14.2(6) . . . . ?
C5 N5 C1 N2 166.9(4) . . . . ?
N3 N4 C2 N7 177.1(4) . . . . ?
N3 N4 C2 N1 -1.8(6) . . . . ?
N8 N7 C2 N4 12.3(7) . . . . ?
N8 N7 C2 N1 -168.7(4) . . . . ?
N2 N1 C2 N4 1.7(6) . . . . ?
N2 N1 C2 N7 -177.2(4) . . . . ?
N5 N6 C3 C4 -0.7(5) . . . . ?
N5 N6 C3 C6 179.3(4) . . . . ?
N6 C3 C4 C5 0.2(6) . . . . ?
C6 C3 C4 C5 -179.8(5) . . . . ?
C3 C4 C5 N5 0.5(5) . . . . ?
C3 C4 C5 C7 179.1(5) . . . . ?
C1 N5 C5 C4 178.0(5) . . . . ?
N6 N5 C5 C4 -1.0(5) . . . . ?
C1 N5 C5 C7 -0.8(8) . . . . ?
N6 N5 C5 C7 -179.7(4) . . . . ?
N10 N9 C8 N8 176.7(5) . . . . ?
N10 N9 C8 N11 -1.5(5) . . . . ?
N7 N8 C8 N9 -5.0(7) . . . . ?
N7 N8 C8 N11 172.8(4) . . . . ?
C9 N11 C8 N9 1.5(5) . . . . ?
N12 N11 C8 N9 175.9(4) . . . . ?
C9 N11 C8 N8 -176.8(4) . . . . ?
N12 N11 C8 N8 -2.4(7) . . . . ?
N9 N10 C9 N11 0.2(6) . . . . ?
C8 N11 C9 N10 -1.1(6) . . . . ?
N12 N11 C9 N10 -174.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_170630c
_database_code_depnum_ccdc_archive 'CCDC 1560577'
loop_
_audit_author_name
_audit_author_address
'Zhen-Li Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_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         'C6 H7 N9 O'
_chemical_formula_sum            'C6 H7 N9 O'
_chemical_formula_weight         221.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.0765(5)
_cell_length_b                   11.8357(9)
_cell_length_c                   15.5195(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.404(2)
_cell_angle_gamma                90
_cell_volume                     922.46(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1269
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.908
_cell_measurement_theta_min      2.654
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4450
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.653
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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                1121
_reflns_number_total             1616
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.022
_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)+(0.0528P)²+0.1690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1129
_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
2.a Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C6(H6)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.2080(4) 0.53472(17) 0.41408(14) 0.0473(6) Uani 1 1 d . . . . .
H1A H 0.238418 0.499234 0.462877 0.057 Uiso 1 1 calc R . . . .
H1B H 0.047379 0.551813 0.392240 0.057 Uiso 1 1 calc R . . . .
N2 N 0.3466(4) 0.61677(16) 0.29403(12) 0.0362(5) Uani 1 1 d . . . . .
H2 H 0.475590 0.653448 0.276815 0.043 Uiso 1 1 d R . . . .
N3 N 0.1064(4) 0.67445(16) 0.27627(12) 0.0380(5) Uani 1 1 d . . . . .
H3 H -0.026018 0.644481 0.243240 0.046 Uiso 1 1 calc R . . . .
N4 N -0.1482(4) 0.83242(17) 0.28532(12) 0.0404(5) Uani 1 1 d . . . . .
N5 N -0.1721(4) 0.93499(16) 0.31602(12) 0.0398(5) Uani 1 1 d . . . . .
N6 N 0.2540(4) 0.91821(16) 0.40012(12) 0.0381(5) Uani 1 1 d . . . . .
N7 N 0.2811(4) 0.81563(15) 0.36958(12) 0.0383(5) Uani 1 1 d . . . . .
N8 N 0.0189(4) 1.08275(15) 0.40326(11) 0.0323(5) Uani 1 1 d . . . . .
N9 N -0.1896(4) 1.15170(17) 0.37481(13) 0.0481(6) Uani 1 1 d . . . . .
O1 O 0.6422(3) 0.54102(13) 0.40044(10) 0.0414(5) Uani 1 1 d . . . . .
C1 C 0.4080(5) 0.56301(18) 0.37264(15) 0.0332(5) Uani 1 1 d . . . . .
C2 C 0.0818(4) 0.77780(19) 0.31114(14) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.0341(4) 0.97353(18) 0.37056(13) 0.0311(5) Uani 1 1 d . . . . .
C4 C 0.2005(5) 1.1354(2) 0.46155(16) 0.0423(6) Uani 1 1 d . . . . .
H4 H 0.359319 1.104858 0.489306 0.051 Uiso 1 1 calc R . . . .
C5 C 0.1099(5) 1.2401(2) 0.47215(17) 0.0468(7) Uani 1 1 d . . . . .
H5 H 0.191158 1.296421 0.508540 0.056 Uiso 1 1 calc R . . . .
C6 C -0.1307(6) 1.2466(2) 0.41735(17) 0.0520(7) Uani 1 1 d . . . . .
H6 H -0.238106 1.310552 0.411334 0.062 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
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.322(3) . ?
N2 H2 0.8599 . ?
N2 N3 1.390(2) . ?
N2 C1 1.371(3) . ?
N3 H3 0.8600 . ?
N3 C2 1.351(3) . ?
N4 N5 1.316(3) . ?
N4 C2 1.344(3) . ?
N5 C3 1.327(3) . ?
N6 N7 1.318(3) . ?
N6 C3 1.317(3) . ?
N7 C2 1.333(3) . ?
N8 N9 1.358(2) . ?
N8 C3 1.395(3) . ?
N8 C4 1.347(3) . ?
N9 C6 1.315(3) . ?
O1 C1 1.232(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.340(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N3 N2 H2 112.1 . . ?
C1 N2 H2 115.2 . . ?
C1 N2 N3 118.89(18) . . ?
N2 N3 H3 120.2 . . ?
C2 N3 N2 119.68(18) . . ?
C2 N3 H3 120.2 . . ?
N5 N4 C2 117.23(19) . . ?
N4 N5 C3 116.26(19) . . ?
C3 N6 N7 117.41(19) . . ?
N6 N7 C2 116.44(18) . . ?
N9 N8 C3 121.36(18) . . ?
C4 N8 N9 111.38(19) . . ?
C4 N8 C3 127.2(2) . . ?
C6 N9 N8 103.9(2) . . ?
N1 C1 N2 117.4(2) . . ?
O1 C1 N1 123.2(2) . . ?
O1 C1 N2 119.5(2) . . ?
N4 C2 N3 116.3(2) . . ?
N7 C2 N3 118.1(2) . . ?
N7 C2 N4 125.5(2) . . ?
N5 C3 N8 118.04(19) . . ?
N6 C3 N5 126.9(2) . . ?
N6 C3 N8 115.0(2) . . ?
N8 C4 H4 126.4 . . ?
C5 C4 N8 107.3(2) . . ?
C5 C4 H4 126.4 . . ?
C4 C5 H5 127.4 . . ?
C4 C5 C6 105.3(2) . . ?
C6 C5 H5 127.4 . . ?
N9 C6 C5 112.1(2) . . ?
N9 C6 H6 123.9 . . ?
C5 C6 H6 123.9 . . ?

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
N2 N3 C2 N4 174.59(19) . . . . ?
N2 N3 C2 N7 -7.4(3) . . . . ?
N3 N2 C1 N1 23.0(3) . . . . ?
N3 N2 C1 O1 -158.6(2) . . . . ?
N4 N5 C3 N6 -3.3(3) . . . . ?
N4 N5 C3 N8 178.77(18) . . . . ?
N5 N4 C2 N3 -177.50(19) . . . . ?
N5 N4 C2 N7 4.7(3) . . . . ?
N6 N7 C2 N3 177.89(19) . . . . ?
N6 N7 C2 N4 -4.3(3) . . . . ?
N7 N6 C3 N5 3.7(3) . . . . ?
N7 N6 C3 N8 -178.35(18) . . . . ?
N8 N9 C6 C5 0.0(3) . . . . ?
N8 C4 C5 C6 -0.4(3) . . . . ?
N9 N8 C3 N5 -5.6(3) . . . . ?
N9 N8 C3 N6 176.29(19) . . . . ?
N9 N8 C4 C5 0.4(3) . . . . ?
C1 N2 N3 C2 78.4(3) . . . . ?
C2 N4 N5 C3 -0.8(3) . . . . ?
C3 N6 N7 C2 0.2(3) . . . . ?
C3 N8 N9 C6 -178.0(2) . . . . ?
C3 N8 C4 C5 177.9(2) . . . . ?
C4 N8 N9 C6 -0.3(3) . . . . ?
C4 N8 C3 N5 177.1(2) . . . . ?
C4 N8 C3 N6 -1.0(3) . . . . ?
C4 C5 C6 N9 0.2(3) . . . . ?

_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_170224c
_database_code_depnum_ccdc_archive 'CCDC 1560576'
loop_
_audit_author_name
_audit_author_address
'Zhen-Li Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_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         'Cl O4, C9 H12 N11'
_chemical_formula_sum            'C9 H12 Cl N11 O4'
_chemical_formula_weight         373.75
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2659(9)
_cell_length_b                   9.2453(14)
_cell_length_c                   11.8288(16)
_cell_angle_alpha                72.190(2)
_cell_angle_beta                 86.574(3)
_cell_angle_gamma                84.812(3)
_cell_volume                     752.99(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2570
_cell_measurement_theta_min      3.9120
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.657
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  0.8767
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.17
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4158
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.023
_diffrn_reflns_theta_max         66.023
_diffrn_reflns_theta_min         3.927
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1658
_reflns_number_total             2617
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     134
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      0.997
_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)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups
2. Restrained distances
 Cl1-O3 = Cl1-O3' = Cl1-O4 = Cl1-O4' = Cl1-O2 = Cl1-O1' = Cl1-O1 = Cl1-O2'
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O1' \\sim O2' \\sim O3' \\sim
O4': within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(Cl1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim
Ueq, Uanis(O4) \\sim Ueq, Uanis(O1') \\sim Ueq, Uanis(O2') \\sim Ueq,
Uanis(O3') \\sim Ueq, Uanis(O4') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Sof(O1')=Sof(O2')=Sof(O3')=Sof(O4')=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=FVAR(1)
5.a Riding coordinates:
 N5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C2(H2), C6(H6)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.33967(14) 0.32542(12) 0.95586(8) 0.0548(3) Uani 1 1 d D U . . .
N1 N 0.1573(5) 0.8316(4) 0.2659(3) 0.0628(9) Uani 1 1 d . . . . .
H1 H 0.161648 0.887202 0.312103 0.075 Uiso 1 1 calc R . . . .
N2 N 0.1484(5) 0.6776(4) 0.3056(3) 0.0589(9) Uani 1 1 d . . . . .
N3 N 0.1511(4) 0.7668(3) 0.1106(3) 0.0475(8) Uani 1 1 d . . . . .
N4 N 0.1399(4) 0.4989(3) 0.1982(3) 0.0559(9) Uani 1 1 d . . . . .
H4 H 0.120835 0.493262 0.128658 0.067 Uiso 1 1 calc R . . . .
N5 N 0.1519(5) 0.7796(4) -0.0116(3) 0.0599(9) Uani 1 1 d . . . . .
H5A H 0.056132 0.734336 -0.025077 0.090 Uiso 1 1 d R . . . .
H5B H 0.256562 0.733687 -0.031067 0.090 Uiso 1 1 d R . . . .
N6 N 0.1320(4) 0.2395(3) 0.2607(3) 0.0521(8) Uani 1 1 d . . . . .
N7 N 0.1629(4) 0.1070(3) 0.3431(3) 0.0497(8) Uani 1 1 d . . . . .
N8 N 0.2357(5) 0.2344(4) 0.4785(3) 0.0641(9) Uani 1 1 d . . . . .
N9 N 0.2082(5) 0.3673(4) 0.3950(3) 0.0659(10) Uani 1 1 d . . . . .
N10 N 0.2553(4) -0.0299(3) 0.5325(3) 0.0499(8) Uani 1 1 d . . . . .
N11 N 0.2325(4) -0.1589(3) 0.5013(3) 0.0534(8) Uani 1 1 d . . . . .
O1 O 0.1789(14) 0.4232(12) 0.9736(12) 0.061(2) Uani 0.610(19) 1 d D U P A 1
O2 O 0.4488(13) 0.2939(14) 1.0601(8) 0.076(2) Uani 0.610(19) 1 d D U P A 1
O3 O 0.2598(13) 0.1899(10) 0.9568(11) 0.087(2) Uani 0.610(19) 1 d D U P A 1
O4 O 0.4584(14) 0.3693(13) 0.8539(8) 0.075(2) Uani 0.610(19) 1 d D U P A 1
O1' O 0.419(2) 0.2337(18) 1.0628(12) 0.076(3) Uani 0.390(19) 1 d D U P A 2
O2' O 0.214(2) 0.4550(17) 0.9561(19) 0.058(3) Uani 0.390(19) 1 d D U P A 2
O3' O 0.261(2) 0.2287(17) 0.9023(15) 0.078(3) Uani 0.390(19) 1 d D U P A 2
O4' O 0.466(2) 0.4191(18) 0.8747(14) 0.076(3) Uani 0.390(19) 1 d D U P A 2
C1 C 0.1459(5) 0.6402(4) 0.2092(3) 0.0485(9) Uani 1 1 d . . . . .
C2 C 0.1585(5) 0.8857(5) 0.1502(4) 0.0588(11) Uani 1 1 d . . . . .
H2 H 0.163556 0.987045 0.104667 0.071 Uiso 1 1 calc R . . . .
C3 C 0.1616(5) 0.3638(4) 0.2885(3) 0.0482(9) Uani 1 1 d . . . . .
C4 C 0.2172(5) 0.1114(4) 0.4488(3) 0.0465(9) Uani 1 1 d . . . . .
C5 C 0.2886(5) -0.2747(4) 0.5945(3) 0.0543(10) Uani 1 1 d . . . . .
C6 C 0.3442(5) -0.2208(5) 0.6856(3) 0.0560(10) Uani 1 1 d . . . . .
H6 H 0.386844 -0.280470 0.759216 0.067 Uiso 1 1 calc R . . . .
C7 C 0.3245(5) -0.0667(5) 0.6467(3) 0.0524(10) Uani 1 1 d . . . . .
C8 C 0.2892(6) -0.4349(5) 0.5933(4) 0.0680(12) Uani 1 1 d . . . . .
H8A H 0.224147 -0.437954 0.525860 0.102 Uiso 1 1 calc GR . . . .
H8B H 0.229417 -0.494215 0.664901 0.102 Uiso 1 1 calc GR . . . .
H8C H 0.414453 -0.476188 0.588370 0.102 Uiso 1 1 calc GR . . . .
C9 C 0.3633(6) 0.0478(5) 0.7068(4) 0.0679(12) Uani 1 1 d . . . . .
H9A H 0.412919 -0.004021 0.783328 0.102 Uiso 1 1 calc GR . . . .
H9B H 0.250683 0.106343 0.716376 0.102 Uiso 1 1 calc GR . . . .
H9C H 0.451225 0.114551 0.659169 0.102 Uiso 1 1 calc GR . . . .


_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
Cl1 O1 1.457(9) . ?
Cl1 O2 1.445(7) . ?
Cl1 O3 1.425(8) . ?
Cl1 O4 1.415(8) . ?
Cl1 O1' 1.412(12) . ?
Cl1 O2' 1.439(14) . ?
Cl1 O3' 1.416(11) . ?
Cl1 O4' 1.430(13) . ?
N1 H1 0.8600 . ?
N1 N2 1.362(4) . ?
N1 C2 1.306(5) . ?
N2 C1 1.290(5) . ?
N3 N5 1.413(4) . ?
N3 C1 1.379(4) . ?
N3 C2 1.326(5) . ?
N4 H4 0.8600 . ?
N4 C1 1.356(4) . ?
N4 C3 1.376(4) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8901 . ?
N6 N7 1.322(4) . ?
N6 C3 1.326(4) . ?
N7 C4 1.346(4) . ?
N8 N9 1.327(4) . ?
N8 C4 1.309(5) . ?
N9 C3 1.335(4) . ?
N10 N11 1.378(4) . ?
N10 C4 1.392(4) . ?
N10 C7 1.401(4) . ?
N11 C5 1.334(5) . ?
C2 H2 0.9300 . ?
C5 C6 1.411(5) . ?
C5 C8 1.485(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.354(5) . ?
C7 C9 1.498(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cl1 O1 106.2(7) . . ?
O3 Cl1 O1 102.6(6) . . ?
O3 Cl1 O2 109.1(4) . . ?
O4 Cl1 O1 121.6(7) . . ?
O4 Cl1 O2 108.5(6) . . ?
O4 Cl1 O3 108.3(5) . . ?
O1' Cl1 O2' 119.9(12) . . ?
O1' Cl1 O3' 108.1(7) . . ?
O1' Cl1 O4' 114.1(9) . . ?
O3' Cl1 O2' 111.3(10) . . ?
O3' Cl1 O4' 110.7(7) . . ?
O4' Cl1 O2' 92.1(11) . . ?
N2 N1 H1 123.7 . . ?
C2 N1 H1 123.7 . . ?
C2 N1 N2 112.6(3) . . ?
C1 N2 N1 103.6(3) . . ?
C1 N3 N5 130.4(3) . . ?
C2 N3 N5 122.9(3) . . ?
C2 N3 C1 106.7(3) . . ?
C1 N4 H4 117.1 . . ?
C1 N4 C3 125.8(3) . . ?
C3 N4 H4 117.1 . . ?
N3 N5 H5A 109.0 . . ?
N3 N5 H5B 109.0 . . ?
H5A N5 H5B 109.5 . . ?
N7 N6 C3 117.2(3) . . ?
N6 N7 C4 116.7(3) . . ?
C4 N8 N9 117.2(3) . . ?
N8 N9 C3 117.1(3) . . ?
N11 N10 C4 118.2(3) . . ?
N11 N10 C7 111.4(3) . . ?
C4 N10 C7 130.4(3) . . ?
C5 N11 N10 104.9(3) . . ?
N2 C1 N3 110.9(3) . . ?
N2 C1 N4 128.0(4) . . ?
N4 C1 N3 121.1(3) . . ?
N1 C2 N3 106.2(3) . . ?
N1 C2 H2 126.9 . . ?
N3 C2 H2 126.9 . . ?
N6 C3 N4 115.7(3) . . ?
N6 C3 N9 125.6(3) . . ?
N9 C3 N4 118.7(3) . . ?
N7 C4 N10 115.5(3) . . ?
N8 C4 N7 126.0(3) . . ?
N8 C4 N10 118.5(3) . . ?
N11 C5 C6 110.8(4) . . ?
N11 C5 C8 121.1(4) . . ?
C6 C5 C8 128.2(4) . . ?
C5 C6 H6 126.2 . . ?
C7 C6 C5 107.7(3) . . ?
C7 C6 H6 126.2 . . ?
N10 C7 C9 124.5(4) . . ?
C6 C7 N10 105.3(3) . . ?
C6 C7 C9 130.2(4) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 N3 -0.6(4) . . . . ?
N1 N2 C1 N4 179.1(4) . . . . ?
N2 N1 C2 N3 -0.2(5) . . . . ?
N5 N3 C1 N2 179.5(3) . . . . ?
N5 N3 C1 N4 -0.2(6) . . . . ?
N5 N3 C2 N1 -179.3(3) . . . . ?
N6 N7 C4 N8 2.6(6) . . . . ?
N6 N7 C4 N10 -177.8(3) . . . . ?
N7 N6 C3 N4 175.9(3) . . . . ?
N7 N6 C3 N9 -4.7(6) . . . . ?
N8 N9 C3 N4 -177.2(4) . . . . ?
N8 N9 C3 N6 3.4(6) . . . . ?
N9 N8 C4 N7 -3.9(6) . . . . ?
N9 N8 C4 N10 176.4(3) . . . . ?
N10 N11 C5 C6 0.9(4) . . . . ?
N10 N11 C5 C8 -178.4(3) . . . . ?
N11 N10 C4 N7 -0.8(5) . . . . ?
N11 N10 C4 N8 178.9(3) . . . . ?
N11 N10 C7 C6 0.0(4) . . . . ?
N11 N10 C7 C9 -179.6(4) . . . . ?
N11 C5 C6 C7 -0.9(5) . . . . ?
C1 N3 C2 N1 -0.1(4) . . . . ?
C1 N4 C3 N6 173.4(3) . . . . ?
C1 N4 C3 N9 -6.1(6) . . . . ?
C2 N1 N2 C1 0.5(5) . . . . ?
C2 N3 C1 N2 0.5(5) . . . . ?
C2 N3 C1 N4 -179.2(3) . . . . ?
C3 N4 C1 N2 -9.8(7) . . . . ?
C3 N4 C1 N3 169.8(3) . . . . ?
C3 N6 N7 C4 1.7(5) . . . . ?
C4 N8 N9 C3 0.9(6) . . . . ?
C4 N10 N11 C5 176.5(3) . . . . ?
C4 N10 C7 C6 -176.6(4) . . . . ?
C4 N10 C7 C9 3.8(6) . . . . ?
C5 C6 C7 N10 0.5(4) . . . . ?
C5 C6 C7 C9 -179.9(4) . . . . ?
C7 N10 N11 C5 -0.6(4) . . . . ?
C7 N10 C4 N7 175.6(3) . . . . ?
C7 N10 C4 N8 -4.6(6) . . . . ?
C8 C5 C6 C7 178.4(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_170716a
_database_code_depnum_ccdc_archive 'CCDC 1842332'
loop_
_audit_author_name
_audit_author_address
'Zhen-Li Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_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         'C9 H11 N11'
_chemical_formula_sum            'C9 H11 N11'
_chemical_formula_weight         273.29
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2540(7)
_cell_length_b                   9.5081(8)
_cell_length_c                   16.5219(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.991(3)
_cell_angle_gamma                90
_cell_volume                     1210.59(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3810
_cell_measurement_theta_min      5.4870
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4080
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.050
_diffrn_reflns_theta_max         66.050
_diffrn_reflns_theta_min         5.465
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                886
_reflns_number_total             2106
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      0.888
_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)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1669
_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
2.a Riding coordinates:
 N4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C7(H7)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.5097(5) 0.1231(4) 0.7027(2) 0.0465(11) Uani 1 1 d . . . . .
N2 N 0.5173(6) 0.1233(4) 0.5756(2) 0.0580(13) Uani 1 1 d . . . . .
H2 H 0.533487 0.149164 0.529226 0.070 Uiso 1 1 calc R . . . .
N3 N 0.4499(6) -0.0070(4) 0.5847(3) 0.0663(15) Uani 1 1 d . . . . .
N4 N 0.5340(6) 0.1651(4) 0.7878(2) 0.0603(14) Uani 1 1 d . . . . .
H4A H 0.434542 0.184244 0.790909 0.072 Uiso 1 1 d R . . . .
H4B H 0.581402 0.097344 0.822789 0.072 Uiso 1 1 d R . . . .
N5 N 0.6217(5) 0.3322(4) 0.6657(2) 0.0465(11) Uani 1 1 d . . . . .
N6 N 0.6366(6) 0.3532(4) 0.5255(2) 0.0519(12) Uani 1 1 d . . . . .
N7 N 0.6951(6) 0.4268(4) 0.4739(2) 0.0512(12) Uani 1 1 d . . . . .
N8 N 0.7862(5) 0.6084(4) 0.5792(2) 0.0512(12) Uani 1 1 d . . . . .
N9 N 0.7293(6) 0.5367(4) 0.6313(2) 0.0507(12) Uani 1 1 d . . . . .
N10 N 0.8443(5) 0.6200(4) 0.4501(2) 0.0479(11) Uani 1 1 d . . . . .
N11 N 0.8150(5) 0.5649(4) 0.3686(2) 0.0546(12) Uani 1 1 d . . . . .
C1 C 0.5547(7) 0.2051(5) 0.6461(3) 0.0458(13) Uani 1 1 d . . . . .
C2 C 0.4482(7) -0.0034(5) 0.6634(3) 0.0590(16) Uani 1 1 d . . . . .
H2A H 0.410361 -0.076704 0.689437 0.071 Uiso 1 1 calc R . . . .
C3 C 0.6656(6) 0.4049(5) 0.6069(3) 0.0419(12) Uani 1 1 d . . . . .
C4 C 0.7750(7) 0.5466(5) 0.5040(3) 0.0467(13) Uani 1 1 d . . . . .
C5 C 1.0013(8) 0.8217(6) 0.5477(3) 0.0754(19) Uani 1 1 d . . . . .
H5A H 1.075899 0.896924 0.543946 0.113 Uiso 1 1 calc GR . . . .
H5B H 1.064588 0.759082 0.593716 0.113 Uiso 1 1 calc GR . . . .
H5C H 0.903965 0.859754 0.559159 0.113 Uiso 1 1 calc GR . . . .
C6 C 0.9384(7) 0.7432(5) 0.4642(3) 0.0569(15) Uani 1 1 d . . . . .
C7 C 0.9654(7) 0.7683(6) 0.3886(3) 0.0602(16) Uani 1 1 d . . . . .
H7 H 1.022677 0.845218 0.376607 0.072 Uiso 1 1 calc R . . . .
C8 C 0.8904(7) 0.6561(6) 0.3323(3) 0.0541(14) Uani 1 1 d . . . . .
C9 C 0.8907(7) 0.6308(6) 0.2431(3) 0.0700(18) Uani 1 1 d . . . . .
H9A H 1.007414 0.636529 0.243956 0.105 Uiso 1 1 calc GR . . . .
H9B H 0.820413 0.700543 0.204303 0.105 Uiso 1 1 calc GR . . . .
H9C H 0.844556 0.538980 0.223842 0.105 Uiso 1 1 calc GR . . . .


_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
N1 N4 1.405(4) . ?
N1 C1 1.368(5) . ?
N1 C2 1.374(6) . ?
N2 H2 0.8600 . ?
N2 N3 1.388(5) . ?
N2 C1 1.340(5) . ?
N3 C2 1.306(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8601 . ?
N5 C1 1.320(6) . ?
N5 C3 1.344(5) . ?
N6 N7 1.321(5) . ?
N6 C3 1.369(5) . ?
N7 C4 1.321(6) . ?
N8 N9 1.309(5) . ?
N8 C4 1.348(6) . ?
N9 C3 1.364(5) . ?
N10 N11 1.383(5) . ?
N10 C4 1.404(5) . ?
N10 C6 1.378(6) . ?
N11 C8 1.329(6) . ?
C2 H2A 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C6 1.489(6) . ?
C6 C7 1.366(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(7) . ?
C8 C9 1.494(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N4 123.1(4) . . ?
C1 N1 C2 108.7(4) . . ?
C2 N1 N4 128.1(4) . . ?
N3 N2 H2 123.2 . . ?
C1 N2 H2 123.2 . . ?
C1 N2 N3 113.6(4) . . ?
C2 N3 N2 103.4(4) . . ?
N1 N4 H4A 108.8 . . ?
N1 N4 H4B 109.1 . . ?
H4A N4 H4B 109.5 . . ?
C1 N5 C3 119.4(4) . . ?
N7 N6 C3 117.9(4) . . ?
N6 N7 C4 117.6(4) . . ?
N9 N8 C4 117.2(4) . . ?
N8 N9 C3 118.4(4) . . ?
N11 N10 C4 117.4(4) . . ?
C6 N10 N11 112.2(4) . . ?
C6 N10 C4 130.4(4) . . ?
C8 N11 N10 104.2(4) . . ?
N2 C1 N1 103.3(4) . . ?
N5 C1 N1 123.1(4) . . ?
N5 C1 N2 133.6(4) . . ?
N1 C2 H2A 124.5 . . ?
N3 C2 N1 111.1(4) . . ?
N3 C2 H2A 124.5 . . ?
N5 C3 N6 121.9(4) . . ?
N5 C3 N9 115.7(4) . . ?
N9 C3 N6 122.2(4) . . ?
N7 C4 N8 125.6(4) . . ?
N7 C4 N10 116.9(4) . . ?
N8 C4 N10 117.3(5) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
N10 C6 C5 124.8(4) . . ?
C7 C6 N10 105.1(5) . . ?
C7 C6 C5 130.0(5) . . ?
C6 C7 H7 126.4 . . ?
C6 C7 C8 107.2(5) . . ?
C8 C7 H7 126.4 . . ?
N11 C8 C7 111.3(4) . . ?
N11 C8 C9 120.4(5) . . ?
C7 C8 C9 128.3(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 C2 N1 0.5(7) . . . . ?
N3 N2 C1 N1 0.2(6) . . . . ?
N3 N2 C1 N5 178.7(6) . . . . ?
N4 N1 C1 N2 177.3(4) . . . . ?
N4 N1 C1 N5 -1.4(8) . . . . ?
N4 N1 C2 N3 -177.4(5) . . . . ?
N6 N7 C4 N8 -7.6(8) . . . . ?
N6 N7 C4 N10 176.8(4) . . . . ?
N7 N6 C3 N5 -175.1(4) . . . . ?
N7 N6 C3 N9 9.5(7) . . . . ?
N8 N9 C3 N5 175.0(4) . . . . ?
N8 N9 C3 N6 -9.4(7) . . . . ?
N9 N8 C4 N7 7.7(8) . . . . ?
N9 N8 C4 N10 -176.7(4) . . . . ?
N10 N11 C8 C7 -0.5(6) . . . . ?
N10 N11 C8 C9 178.4(4) . . . . ?
N10 C6 C7 C8 -1.7(6) . . . . ?
N11 N10 C4 N7 3.4(7) . . . . ?
N11 N10 C4 N8 -172.6(4) . . . . ?
N11 N10 C6 C5 -175.4(5) . . . . ?
N11 N10 C6 C7 1.5(6) . . . . ?
C1 N1 C2 N3 -0.4(7) . . . . ?
C1 N2 N3 C2 -0.5(6) . . . . ?
C1 N5 C3 N6 2.5(7) . . . . ?
C1 N5 C3 N9 178.2(5) . . . . ?
C2 N1 C1 N2 0.1(6) . . . . ?
C2 N1 C1 N5 -178.5(5) . . . . ?
C3 N5 C1 N1 178.7(4) . . . . ?
C3 N5 C1 N2 0.5(9) . . . . ?
C3 N6 N7 C4 -1.1(7) . . . . ?
C4 N8 N9 C3 1.0(7) . . . . ?
C4 N10 N11 C8 178.6(4) . . . . ?
C4 N10 C6 C5 5.6(9) . . . . ?
C4 N10 C6 C7 -177.6(5) . . . . ?
C5 C6 C7 C8 174.9(6) . . . . ?
C6 N10 N11 C8 -0.6(5) . . . . ?
C6 N10 C4 N7 -177.5(5) . . . . ?
C6 N10 C4 N8 6.5(8) . . . . ?
C6 C7 C8 N11 1.5(7) . . . . ?
C6 C7 C8 C9 -177.3(5) . . . . ?

_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_170813b
_database_code_depnum_ccdc_archive 'CCDC 1842333'
loop_
_audit_author_name
_audit_author_address
'Zhen-Li Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_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         'Cl O4, C6 H8 N9 O'
_chemical_formula_sum            'C6 H8 Cl N9 O5'
_chemical_formula_weight         321.66
_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'
Cl Cl 0.1484 0.1585 '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                   5.1120(5)
_cell_length_b                   25.160(2)
_cell_length_c                   9.8231(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.650(2)
_cell_angle_gamma                90
_cell_volume                     1254.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1180
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.042
_cell_measurement_theta_min      2.682
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5650
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.642
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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                1292
_reflns_number_total             2182
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.1039
_refine_ls_restrained_S_all      1.079
_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)+(0.1009P)²+4.6821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2325
_refine_ls_wR_factor_ref         0.2616
_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
2.a Riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N9(H9), C4(H4), C5(H5), C6(H6)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.4683(4) 0.13063(8) 0.8789(2) 0.0329(6) Uani 1 1 d . . . . .
N1 N 1.0879(14) 0.2852(3) 0.5960(7) 0.0387(18) Uani 1 1 d . . . . .
H1A H 1.151854 0.315805 0.579674 0.046 Uiso 1 1 calc R . . . .
H1B H 1.149645 0.257021 0.561569 0.046 Uiso 1 1 calc R . . . .
N2 N 0.7956(13) 0.2340(2) 0.7002(7) 0.0330(17) Uani 1 1 d . . . . .
H2 H 0.676335 0.231934 0.754889 0.040 Uiso 1 1 calc R . . . .
N3 N 0.8832(13) 0.1881(3) 0.6398(6) 0.0334(16) Uani 1 1 d . . . . .
H3 H 0.947817 0.166289 0.708206 0.040 Uiso 1 1 d R . . . .
N4 N 0.4757(15) 0.1812(2) 0.4979(6) 0.0319(16) Uani 1 1 d . . . . .
N5 N 0.3155(13) 0.1510(2) 0.4131(6) 0.0310(16) Uani 1 1 d . . . . .
N6 N 0.6231(13) 0.0780(3) 0.4502(6) 0.0343(16) Uani 1 1 d . . . . .
N7 N 0.7839(14) 0.1077(3) 0.5338(7) 0.0369(17) Uani 1 1 d . . . . .
N8 N 0.2326(13) 0.0686(2) 0.3080(6) 0.0313(16) Uani 1 1 d . . . . .
N9 N 0.0122(13) 0.0862(2) 0.2297(6) 0.0306(16) Uani 1 1 d . . . . .
H9 H -0.041804 0.118616 0.225359 0.037 Uiso 1 1 calc R . . . .
O1 O 0.7957(11) 0.3221(2) 0.7277(5) 0.0351(14) Uani 1 1 d . . . . .
O2 O 0.7530(12) 0.1260(3) 0.8978(6) 0.0522(17) Uani 1 1 d . . . . .
O3 O 0.3575(13) 0.1104(3) 0.9983(6) 0.0516(17) Uani 1 1 d . . . . .
O4 O 0.3894(14) 0.1857(2) 0.8595(7) 0.058(2) Uani 1 1 d . . . . .
O5 O 0.3608(15) 0.1027(3) 0.7580(7) 0.069(2) Uani 1 1 d . . . . .
C1 C 0.8980(16) 0.2813(3) 0.6726(8) 0.0317(19) Uani 1 1 d . . . . .
C2 C 0.7042(15) 0.1594(3) 0.5545(7) 0.0246(17) Uani 1 1 d . . . . .
C3 C 0.3936(16) 0.1011(3) 0.3934(7) 0.0265(17) Uani 1 1 d . . . . .
C4 C 0.257(2) 0.0152(3) 0.2855(8) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.392671 -0.006224 0.325424 0.054 Uiso 1 1 calc R . . . .
C5 C 0.0486(18) -0.0017(3) 0.1945(9) 0.044(2) Uani 1 1 d . . . . .
H5 H 0.015117 -0.035976 0.161751 0.053 Uiso 1 1 calc R . . . .
C6 C -0.1071(16) 0.0456(3) 0.1608(8) 0.037(2) Uani 1 1 d . . . . .
H6 H -0.262617 0.047283 0.101586 0.044 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
Cl1 O2 1.451(6) . ?
Cl1 O3 1.452(6) . ?
Cl1 O4 1.449(6) . ?
Cl1 O5 1.434(7) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.299(10) . ?
N2 H2 0.8600 . ?
N2 N3 1.396(8) . ?
N2 C1 1.341(9) . ?
N3 H3 0.9000 . ?
N3 C2 1.372(9) . ?
N4 N5 1.336(9) . ?
N4 C2 1.350(10) . ?
N5 C3 1.338(9) . ?
N6 N7 1.323(9) . ?
N6 C3 1.369(10) . ?
N7 C2 1.386(9) . ?
N8 N9 1.363(9) . ?
N8 C3 1.375(10) . ?
N8 C4 1.369(10) . ?
N9 H9 0.8600 . ?
N9 C6 1.335(9) . ?
O1 C1 1.298(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.447(11) . ?
C6 H6 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
O2 Cl1 O3 110.4(4) . . ?
O4 Cl1 O2 110.6(4) . . ?
O4 Cl1 O3 108.3(4) . . ?
O5 Cl1 O2 110.4(4) . . ?
O5 Cl1 O3 110.5(4) . . ?
O5 Cl1 O4 106.6(5) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N3 N2 H2 120.1 . . ?
C1 N2 H2 120.1 . . ?
C1 N2 N3 119.8(6) . . ?
N2 N3 H3 107.1 . . ?
C2 N3 N2 118.1(6) . . ?
C2 N3 H3 107.3 . . ?
N5 N4 C2 117.7(6) . . ?
N4 N5 C3 116.9(7) . . ?
N7 N6 C3 117.0(6) . . ?
N6 N7 C2 116.7(7) . . ?
N9 N8 C3 123.3(6) . . ?
N9 N8 C4 108.2(6) . . ?
C4 N8 C3 128.6(7) . . ?
N8 N9 H9 125.2 . . ?
C6 N9 N8 109.7(6) . . ?
C6 N9 H9 125.2 . . ?
N1 C1 N2 121.2(8) . . ?
O1 C1 N1 123.2(7) . . ?
O1 C1 N2 115.6(7) . . ?
N3 C2 N7 113.4(7) . . ?
N4 C2 N3 121.5(6) . . ?
N4 C2 N7 125.2(7) . . ?
N5 C3 N6 126.6(7) . . ?
N5 C3 N8 118.6(7) . . ?
N6 C3 N8 114.8(6) . . ?
N8 C4 H4 125.3 . . ?
N8 C4 C5 109.3(8) . . ?
C5 C4 H4 125.3 . . ?
C4 C5 H5 127.5 . . ?
C4 C5 C6 105.0(7) . . ?
C6 C5 H5 127.5 . . ?
N9 C6 C5 107.9(7) . . ?
N9 C6 H6 126.1 . . ?
C5 C6 H6 126.1 . . ?

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
N2 N3 C2 N4 19.1(10) . . . . ?
N2 N3 C2 N7 -161.3(6) . . . . ?
N3 N2 C1 N1 -3.6(12) . . . . ?
N3 N2 C1 O1 176.7(7) . . . . ?
N4 N5 C3 N6 -0.9(11) . . . . ?
N4 N5 C3 N8 179.3(6) . . . . ?
N5 N4 C2 N3 178.2(6) . . . . ?
N5 N4 C2 N7 -1.4(11) . . . . ?
N6 N7 C2 N3 -178.6(6) . . . . ?
N6 N7 C2 N4 1.0(11) . . . . ?
N7 N6 C3 N5 0.5(11) . . . . ?
N7 N6 C3 N8 -179.7(6) . . . . ?
N8 N9 C6 C5 -1.1(9) . . . . ?
N8 C4 C5 C6 0.5(10) . . . . ?
N9 N8 C3 N5 7.9(11) . . . . ?
N9 N8 C3 N6 -171.9(6) . . . . ?
N9 N8 C4 C5 -1.2(10) . . . . ?
C1 N2 N3 C2 -117.9(8) . . . . ?
C2 N4 N5 C3 1.2(10) . . . . ?
C3 N6 N7 C2 -0.5(10) . . . . ?
C3 N8 N9 C6 -178.3(7) . . . . ?
C3 N8 C4 C5 178.5(8) . . . . ?
C4 N8 N9 C6 1.4(9) . . . . ?
C4 N8 C3 N5 -171.7(8) . . . . ?
C4 N8 C3 N6 8.4(12) . . . . ?
C4 C5 C6 N9 0.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
