# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

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

data_2py
_database_code_depnum_ccdc_archive 'CCDC 1954914'
loop_
_audit_author_name
_audit_author_address
'Yuichiro Mutoh'
;Kagawa University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N4 O2'
_chemical_formula_weight         344.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7189(8)
_cell_length_b                   12.8637(13)
_cell_length_c                   16.8268(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.3060(10)
_cell_angle_gamma                90
_cell_volume                     1670.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    4387

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      28.28


_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.926

_exptl_absorpt_correction_T_max  0.981

_exptl_absorpt_process_details   'SADABS 2016/2'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            9023
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3734
_reflns_number_gt                3293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'

_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.5087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3734
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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_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 0.85617(15) 0.29423(9) 0.42760(7) 0.0215(2) Uani 1 1 d . . . . .
H1 H 0.777282 0.331364 0.391682 0.032 Uiso 1 1 calc R U . . .
H1A H 0.889577 0.227881 0.403504 0.032 Uiso 1 1 calc R U . . .
H1B H 0.959902 0.336499 0.436986 0.032 Uiso 1 1 calc R U . . .
O1 O 0.77103(11) 0.27513(6) 0.50161(5) 0.02115(19) Uani 1 1 d . . . . .
C2 C 0.71979(14) 0.35951(8) 0.54385(6) 0.0168(2) Uani 1 1 d . . . . .
C3 C 0.74007(14) 0.46090(8) 0.52091(6) 0.0166(2) Uani 1 1 d . . . . .
H3 H 0.793461 0.476682 0.471626 0.020 Uiso 1 1 calc R U . . .
C4 C 0.68138(13) 0.54227(8) 0.57075(6) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.70700(12) 0.64284(7) 0.54850(5) 0.0155(2) Uani 1 1 d . . . . .
C5 C 0.65274(13) 0.71646(8) 0.59741(6) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.70336(13) 0.82521(8) 0.57716(6) 0.0152(2) Uani 1 1 d . . . . .
N2 N 0.79243(12) 0.87512(7) 0.63414(5) 0.0181(2) Uani 1 1 d . . . . .
C7 C 0.83980(16) 0.97339(9) 0.61862(7) 0.0220(2) Uani 1 1 d . . . . .
H7 H 0.903578 1.009949 0.658154 0.026 Uiso 1 1 calc R U . . .
C8 C 0.80123(16) 1.02452(9) 0.54848(7) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.835739 1.094640 0.540592 0.028 Uiso 1 1 calc R U . . .
C9 C 0.71118(17) 0.97117(10) 0.49004(7) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.683008 1.004084 0.441109 0.030 Uiso 1 1 calc R U . . .
C10 C 0.66251(16) 0.86878(9) 0.50388(7) 0.0216(2) Uani 1 1 d . . . . .
H10 H 0.603005 0.829706 0.464363 0.026 Uiso 1 1 calc R U . . .
C11 C 0.56169(13) 0.69200(8) 0.66890(6) 0.0150(2) Uani 1 1 d . . . . .
C12 C 0.48248(13) 0.77341(8) 0.72047(6) 0.0153(2) Uani 1 1 d . . . . .
N3 N 0.41594(12) 0.85719(7) 0.68344(6) 0.0181(2) Uani 1 1 d . . . . .
C13 C 0.34374(15) 0.92997(9) 0.72935(7) 0.0206(2) Uani 1 1 d . . . . .
H13 H 0.295515 0.989479 0.704165 0.025 Uiso 1 1 calc R U . . .
C14 C 0.33502(15) 0.92379(9) 0.81155(7) 0.0214(2) Uani 1 1 d . . . . .
H14 H 0.285103 0.978575 0.841571 0.026 Uiso 1 1 calc R U . . .
C15 C 0.40042(15) 0.83631(10) 0.84894(7) 0.0212(2) Uani 1 1 d . . . . .
H15 H 0.394430 0.829117 0.905050 0.025 Uiso 1 1 calc R U . . .
C16 C 0.47499(14) 0.75930(9) 0.80257(7) 0.0182(2) Uani 1 1 d . . . . .
H16 H 0.520179 0.697982 0.826354 0.022 Uiso 1 1 calc R U . . .
N4 N 0.54019(11) 0.59436(7) 0.69230(5) 0.01572(19) Uani 1 1 d . . . . .
C17 C 0.60325(13) 0.51794(8) 0.64456(6) 0.0151(2) Uani 1 1 d . . . . .
C18 C 0.58654(14) 0.41251(8) 0.66817(6) 0.0166(2) Uani 1 1 d . . . . .
H18 H 0.537204 0.395936 0.718196 0.020 Uiso 1 1 calc R U . . .
C19 C 0.64124(14) 0.33506(8) 0.61910(7) 0.0165(2) Uani 1 1 d . . . . .
O2 O 0.63054(11) 0.23152(6) 0.63462(5) 0.02002(19) Uani 1 1 d . . . . .
C20 C 0.55276(16) 0.20201(9) 0.70847(7) 0.0226(3) Uani 1 1 d . . . . .
H20 H 0.611272 0.238126 0.752313 0.034 Uiso 1 1 calc R U . . .
H20A H 0.564046 0.126733 0.715808 0.034 Uiso 1 1 calc R U . . .
H20B H 0.429810 0.221005 0.707766 0.034 Uiso 1 1 calc R U . . .


_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 O1 1.4324(14) . ?
C1 H1 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
O1 C2 1.3574(13) . ?
C2 C3 1.3694(15) . ?
C2 C19 1.4415(15) . ?
C3 C4 1.4171(15) . ?
C3 H3 0.9500 . ?
C4 N1 1.3616(14) . ?
C4 C17 1.4185(15) . ?
N1 C5 1.3242(14) . ?
C5 C11 1.4315(15) . ?
C5 C6 1.4924(15) . ?
C6 N2 1.3406(14) . ?
C6 C10 1.3892(15) . ?
N2 C7 1.3420(15) . ?
C7 C8 1.3822(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3834(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3896(17) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N4 1.3269(14) . ?
C11 C12 1.4930(15) . ?
C12 N3 1.3454(14) . ?
C12 C16 1.3949(15) . ?
N3 C13 1.3373(14) . ?
C13 C14 1.3874(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3833(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3880(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N4 C17 1.3612(14) . ?
C17 C18 1.4194(15) . ?
C18 C19 1.3626(16) . ?
C18 H18 0.9500 . ?
C19 O2 1.3598(13) . ?
O2 C20 1.4341(14) . ?
C20 H20 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1 109.5 . . ?
O1 C1 H1A 109.5 . . ?
H1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 O1 C1 117.02(9) . . ?
O1 C2 C3 125.45(10) . . ?
O1 C2 C19 114.24(9) . . ?
C3 C2 C19 120.30(10) . . ?
C2 C3 C4 119.96(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C4 C3 119.45(10) . . ?
N1 C4 C17 120.89(10) . . ?
C3 C4 C17 119.60(10) . . ?
C5 N1 C4 117.50(9) . . ?
N1 C5 C11 121.56(10) . . ?
N1 C5 C6 116.39(9) . . ?
C11 C5 C6 121.89(9) . . ?
N2 C6 C10 123.69(10) . . ?
N2 C6 C5 114.80(9) . . ?
C10 C6 C5 121.49(10) . . ?
C6 N2 C7 116.82(10) . . ?
N2 C7 C8 123.83(11) . . ?
N2 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.43(11) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C10 119.10(11) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C6 C10 C9 118.09(11) . . ?
C6 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
N4 C11 C5 121.35(10) . . ?
N4 C11 C12 116.06(9) . . ?
C5 C11 C12 122.59(10) . . ?
N3 C12 C16 123.03(10) . . ?
N3 C12 C11 116.70(9) . . ?
C16 C12 C11 120.24(10) . . ?
C13 N3 C12 116.91(10) . . ?
N3 C13 C14 123.94(11) . . ?
N3 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C15 C14 C13 118.72(10) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 118.44(10) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C12 118.91(11) . . ?
C15 C16 H16 120.5 . . ?
C12 C16 H16 120.5 . . ?
C11 N4 C17 117.56(9) . . ?
N4 C17 C4 120.83(10) . . ?
N4 C17 C18 119.44(10) . . ?
C4 C17 C18 119.71(10) . . ?
C19 C18 C17 120.01(10) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O2 C19 C18 125.48(10) . . ?
O2 C19 C2 114.13(9) . . ?
C18 C19 C2 120.39(10) . . ?
C19 O2 C20 116.87(9) . . ?
O2 C20 H20 109.5 . . ?
O2 C20 H20A 109.5 . . ?
H20 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20 C20 H20B 109.5 . . ?
H20A C20 H20B 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
C1 O1 C2 C3 1.20(15) . . . . ?
C1 O1 C2 C19 -177.66(9) . . . . ?
O1 C2 C3 C4 -179.73(10) . . . . ?
C19 C2 C3 C4 -0.93(16) . . . . ?
C2 C3 C4 N1 177.99(9) . . . . ?
C2 C3 C4 C17 0.57(16) . . . . ?
C3 C4 N1 C5 -178.90(9) . . . . ?
C17 C4 N1 C5 -1.52(15) . . . . ?
C4 N1 C5 C11 -3.48(15) . . . . ?
C4 N1 C5 C6 171.99(9) . . . . ?
N1 C5 C6 N2 -122.58(10) . . . . ?
C11 C5 C6 N2 52.87(14) . . . . ?
N1 C5 C6 C10 56.26(14) . . . . ?
C11 C5 C6 C10 -128.28(12) . . . . ?
C10 C6 N2 C7 1.54(16) . . . . ?
C5 C6 N2 C7 -179.64(10) . . . . ?
C6 N2 C7 C8 0.34(17) . . . . ?
N2 C7 C8 C9 -1.18(19) . . . . ?
C7 C8 C9 C10 0.18(18) . . . . ?
N2 C6 C10 C9 -2.48(17) . . . . ?
C5 C6 C10 C9 178.78(10) . . . . ?
C8 C9 C10 C6 1.51(18) . . . . ?
N1 C5 C11 N4 5.50(16) . . . . ?
C6 C5 C11 N4 -169.72(9) . . . . ?
N1 C5 C11 C12 -173.18(9) . . . . ?
C6 C5 C11 C12 11.59(15) . . . . ?
N4 C11 C12 N3 -144.11(10) . . . . ?
C5 C11 C12 N3 34.64(14) . . . . ?
N4 C11 C12 C16 33.91(14) . . . . ?
C5 C11 C12 C16 -147.34(11) . . . . ?
C16 C12 N3 C13 1.57(16) . . . . ?
C11 C12 N3 C13 179.53(9) . . . . ?
C12 N3 C13 C14 0.35(17) . . . . ?
N3 C13 C14 C15 -1.74(18) . . . . ?
C13 C14 C15 C16 1.20(17) . . . . ?
C14 C15 C16 C12 0.56(16) . . . . ?
N3 C12 C16 C15 -2.04(17) . . . . ?
C11 C12 C16 C15 -179.94(10) . . . . ?
C5 C11 N4 C17 -1.98(15) . . . . ?
C12 C11 N4 C17 176.79(9) . . . . ?
C11 N4 C17 C4 -2.99(15) . . . . ?
C11 N4 C17 C18 178.60(9) . . . . ?
N1 C4 C17 N4 4.97(15) . . . . ?
C3 C4 C17 N4 -177.66(9) . . . . ?
N1 C4 C17 C18 -176.63(9) . . . . ?
C3 C4 C17 C18 0.75(15) . . . . ?
N4 C17 C18 C19 176.70(10) . . . . ?
C4 C17 C18 C19 -1.73(16) . . . . ?
C17 C18 C19 O2 -179.27(10) . . . . ?
C17 C18 C19 C2 1.39(16) . . . . ?
O1 C2 C19 O2 -0.53(13) . . . . ?
C3 C2 C19 O2 -179.46(9) . . . . ?
O1 C2 C19 C18 178.88(9) . . . . ?
C3 C2 C19 C18 -0.05(16) . . . . ?
C18 C19 O2 C20 0.93(15) . . . . ?
C2 C19 O2 C20 -179.69(9) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_ISDrev
_database_code_depnum_ccdc_archive 'CCDC 1954916'
loop_
_audit_author_name
_audit_author_address
'Yuichiro Mutoh'
;Kagawa University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   6.8207(13)
_cell_length_b                   14.526(3)
_cell_length_c                   16.989(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.214(2)
_cell_angle_gamma                90
_cell_volume                     1680.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    2797

_cell_measurement_theta_min      2.40

_cell_measurement_theta_max      27.90


_exptl_crystal_description       prism

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.933

_exptl_absorpt_correction_T_max  0.990

_exptl_absorpt_process_details   'SADABS 2016/2'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            4453
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.846
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1840
_reflns_number_gt                1704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'

_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+1.1298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0142(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1840
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_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 0.24259(17) 0.29832(7) 0.34143(6) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.122160 0.329895 0.322349 0.030 Uiso 1 1 calc R U . . .
H2 H 0.236818 0.233730 0.324791 0.030 Uiso 1 1 calc R U . . .
H3 H 0.356246 0.328146 0.319458 0.030 Uiso 1 1 calc R U . . .
O1 O 0.26089(11) 0.30295(5) 0.42546(4) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.25671(14) 0.38830(7) 0.45787(6) 0.0143(2) Uani 1 1 d . . . . .
C3 C 0.26618(14) 0.46963(7) 0.41748(6) 0.0148(2) Uani 1 1 d . . . . .
H4 H 0.276727 0.469251 0.361962 0.018 Uiso 1 1 calc R U . . .
C4 C 0.26022(14) 0.55453(7) 0.45872(6) 0.0136(2) Uani 1 1 d . . . . .
N1 N 0.28153(12) 0.63473(6) 0.41897(5) 0.0144(2) Uani 1 1 d . . . . .
C5 C 0.27250(14) 0.71282(7) 0.45937(6) 0.0140(2) Uani 1 1 d . . . . .
C6 C 0.32308(15) 0.79783(7) 0.41607(6) 0.0147(2) Uani 1 1 d . . . . .
C7 C 0.25088(15) 0.81031(7) 0.33838(6) 0.0163(2) Uani 1 1 d . . . . .
H5 H 0.159693 0.767367 0.315286 0.020 Uiso 1 1 calc R U . . .
C8 C 0.31074(16) 0.88491(7) 0.29423(6) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.260749 0.892711 0.241329 0.023 Uiso 1 1 calc R U . . .
C9 C 0.44407(17) 0.94798(7) 0.32791(7) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.485219 0.999023 0.298009 0.025 Uiso 1 1 calc R U . . .
C10 C 0.51714(16) 0.93629(7) 0.40539(7) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.608373 0.979357 0.428269 0.024 Uiso 1 1 calc R U . . .
C11 C 0.45709(15) 0.86179(7) 0.44945(6) 0.0174(2) Uani 1 1 d . . . . .
H9 H 0.507123 0.854237 0.502374 0.021 Uiso 1 1 calc R U . . .


_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 O1 1.4276(13) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 H3 0.9800 . ?
O1 C2 1.3577(12) . ?
C2 C3 1.3696(14) . ?
C2 C2 1.439(2) 2_556 ?
C3 C4 1.4201(14) . ?
C3 H4 0.9500 . ?
C4 N1 1.3584(13) . ?
C4 C4 1.417(2) 2_556 ?
N1 C5 1.3291(13) . ?
C5 C5 1.431(2) 2_556 ?
C5 C6 1.4877(14) . ?
C6 C7 1.3946(15) . ?
C6 C11 1.4007(15) . ?
C7 C8 1.3920(14) . ?
C7 H5 0.9500 . ?
C8 C9 1.3912(16) . ?
C8 H6 0.9500 . ?
C9 C10 1.3916(17) . ?
C9 H7 0.9500 . ?
C10 C11 1.3906(15) . ?
C10 H8 0.9500 . ?
C11 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 116.49(8) . . ?
O1 C2 C3 125.58(10) . . ?
O1 C2 C2 114.04(5) . 2_556 ?
C3 C2 C2 120.37(6) . 2_556 ?
C2 C3 C4 119.90(10) . . ?
C2 C3 H4 120.0 . . ?
C4 C3 H4 120.0 . . ?
N1 C4 C4 120.74(6) . 2_556 ?
N1 C4 C3 119.52(10) . . ?
C4 C4 C3 119.69(6) 2_556 . ?
C5 N1 C4 117.77(9) . . ?
N1 C5 C5 121.12(6) . 2_556 ?
N1 C5 C6 115.75(9) . . ?
C5 C5 C6 123.04(6) 2_556 . ?
C7 C6 C11 118.99(9) . . ?
C7 C6 C5 119.77(9) . . ?
C11 C6 C5 120.97(9) . . ?
C8 C7 C6 120.83(10) . . ?
C8 C7 H5 119.6 . . ?
C6 C7 H5 119.6 . . ?
C9 C8 C7 119.73(10) . . ?
C9 C8 H6 120.1 . . ?
C7 C8 H6 120.1 . . ?
C8 C9 C10 119.99(10) . . ?
C8 C9 H7 120.0 . . ?
C10 C9 H7 120.0 . . ?
C11 C10 C9 120.23(10) . . ?
C11 C10 H8 119.9 . . ?
C9 C10 H8 119.9 . . ?
C10 C11 C6 120.24(10) . . ?
C10 C11 H9 119.9 . . ?
C6 C11 H9 119.9 . . ?

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
C1 O1 C2 C3 -10.38(15) . . . . ?
C1 O1 C2 C2 170.35(10) . . . 2_556 ?
O1 C2 C3 C4 179.97(9) . . . . ?
C2 C2 C3 C4 -0.81(18) 2_556 . . . ?
C2 C3 C4 N1 176.07(9) . . . . ?
C2 C3 C4 C4 -1.50(17) . . . 2_556 ?
C4 C4 N1 C5 -3.34(17) 2_556 . . . ?
C3 C4 N1 C5 179.12(9) . . . . ?
C4 N1 C5 C5 -4.50(17) . . . 2_556 ?
C4 N1 C5 C6 172.11(8) . . . . ?
N1 C5 C6 C7 43.27(13) . . . . ?
C5 C5 C6 C7 -140.19(13) 2_556 . . . ?
N1 C5 C6 C11 -130.69(10) . . . . ?
C5 C5 C6 C11 45.85(17) 2_556 . . . ?
C11 C6 C7 C8 0.15(15) . . . . ?
C5 C6 C7 C8 -173.93(9) . . . . ?
C6 C7 C8 C9 -0.08(16) . . . . ?
C7 C8 C9 C10 0.06(16) . . . . ?
C8 C9 C10 C11 -0.12(17) . . . . ?
C9 C10 C11 C6 0.19(16) . . . . ?
C7 C6 C11 C10 -0.21(15) . . . . ?
C5 C6 C11 C10 173.80(10) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.063


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/a
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_isd41_sq
_database_code_depnum_ccdc_archive 'CCDC 1954915'
loop_
_audit_author_name
_audit_author_address
'Yuichiro Mutoh'
;Kagawa University
Japan
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 Cl3 N4 O5'
_chemical_formula_weight         507.79

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0736(17)
_cell_length_b                   9.491(2)
_cell_length_c                   18.928(4)
_cell_angle_alpha                78.032(2)
_cell_angle_beta                 85.170(3)
_cell_angle_gamma                85.818(3)
_cell_volume                     1236.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    4835

_cell_measurement_theta_min      2.21

_cell_measurement_theta_max      27.53


_exptl_crystal_description       prism

_exptl_crystal_colour            ?

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.408
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.913

_exptl_absorpt_correction_T_max  0.988

_exptl_absorpt_process_details   'SADABS 2016/2'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13574
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5471
_reflns_number_gt                4709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 Structure factors included contributions from the .fab file.

 _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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+8.1309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5471
_refine_ls_number_parameters     318
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1736
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.344
_refine_ls_shift/su_max          0.001
_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_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 0.6484(8) 0.1631(5) 0.6584(3) 0.0288(11) Uani 1 1 d . . . . .
H1 H 0.527662 0.158798 0.637231 0.043 Uiso 1 1 calc R U . . .
H1A H 0.636922 0.118976 0.710056 0.043 Uiso 1 1 calc R U . . .
H1B H 0.749241 0.110526 0.633906 0.043 Uiso 1 1 calc R U . . .
O1 O 0.6947(5) 0.3122(4) 0.64942(16) 0.0246(7) Uani 1 1 d . . . . .
C2 C 0.7183(6) 0.3858(5) 0.5802(2) 0.0193(9) Uani 1 1 d . . . . .
C3 C 0.6902(6) 0.3336(5) 0.5203(2) 0.0165(8) Uani 1 1 d . . . . .
H3 H 0.654970 0.237275 0.524848 0.020 Uiso 1 1 calc R U . . .
C4 C 0.7142(6) 0.4249(4) 0.4514(2) 0.0135(8) Uani 1 1 d . . . . .
N1 N 0.6703(5) 0.3794(4) 0.39158(18) 0.0136(7) Uani 1 1 d . . . . .
C5 C 0.7010(6) 0.4657(4) 0.3276(2) 0.0130(8) Uani 1 1 d . . . . .
C6 C 0.6162(6) 0.4135(4) 0.2688(2) 0.0141(8) Uani 1 1 d . . . . .
N2 N 0.6302(5) 0.2707(4) 0.27277(18) 0.0155(7) Uani 1 1 d . . . . .
H2 H 0.704(7) 0.204(5) 0.308(3) 0.019 Uiso 1 1 d . U . . .
C7 C 0.5481(6) 0.2057(5) 0.2277(2) 0.0181(8) Uani 1 1 d . . . . .
H7 H 0.565318 0.104090 0.232003 0.022 Uiso 1 1 calc R U . . .
C8 C 0.4391(6) 0.2861(5) 0.1751(2) 0.0187(9) Uani 1 1 d . . . . .
H8 H 0.377914 0.241215 0.143506 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4207(6) 0.4359(5) 0.1695(2) 0.0193(9) Uani 1 1 d . . . . .
H9 H 0.346560 0.493747 0.133553 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5097(6) 0.5001(4) 0.2159(2) 0.0155(8) Uani 1 1 d . . . . .
H10 H 0.498373 0.601761 0.211848 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7940(6) 0.5965(4) 0.3204(2) 0.0137(8) Uani 1 1 d . . . . .
C12 C 0.8757(6) 0.6821(4) 0.2514(2) 0.0145(8) Uani 1 1 d . . . . .
N3 N 0.9129(5) 0.8185(4) 0.25311(19) 0.0161(7) Uani 1 1 d . . . . .
H21 H 0.876(7) 0.855(5) 0.295(3) 0.019 Uiso 1 1 d . U . . .
C13 C 0.9917(6) 0.9102(5) 0.1963(2) 0.0209(9) Uani 1 1 d . . . . .
H13 H 1.013062 1.005850 0.200213 0.025 Uiso 1 1 calc R U . . .
C14 C 1.0415(6) 0.8648(5) 0.1322(2) 0.0223(9) Uani 1 1 d . . . . .
H14 H 1.096095 0.928534 0.091336 0.027 Uiso 1 1 calc R U . . .
C15 C 1.0101(6) 0.7243(5) 0.1287(2) 0.0222(9) Uani 1 1 d . . . . .
H15 H 1.044968 0.690558 0.085316 0.027 Uiso 1 1 calc R U . . .
C16 C 0.9282(6) 0.6323(5) 0.1883(2) 0.0182(9) Uani 1 1 d . . . . .
H16 H 0.908143 0.535581 0.185804 0.022 Uiso 1 1 calc R U . . .
N4 N 0.8242(5) 0.6465(4) 0.37843(19) 0.0142(7) Uani 1 1 d . . . . .
C17 C 0.7778(5) 0.5664(4) 0.4449(2) 0.0146(8) Uani 1 1 d . . . . .
C18 C 0.8007(6) 0.6210(5) 0.5075(2) 0.0165(8) Uani 1 1 d . . . . .
H18 H 0.836586 0.717039 0.503458 0.020 Uiso 1 1 calc R U . . .
C19 C 0.7703(6) 0.5333(5) 0.5739(2) 0.0179(9) Uani 1 1 d . . . . .
O2 O 0.7875(5) 0.5697(4) 0.63847(17) 0.0240(7) Uani 1 1 d . . . . .
C20 C 0.8300(7) 0.7169(6) 0.6364(3) 0.0303(11) Uani 1 1 d . . . . .
H20 H 0.949535 0.738277 0.607224 0.046 Uiso 1 1 calc R U . . .
H20A H 0.842152 0.730381 0.685698 0.046 Uiso 1 1 calc R U . . .
H20B H 0.727095 0.782225 0.614719 0.046 Uiso 1 1 calc R U . . .
Cl1 Cl 0.52163(15) 0.90960(11) 0.14870(5) 0.0188(2) Uani 1 1 d . . . . .
Cl2 Cl 0.03847(16) 0.68367(12) -0.11220(6) 0.0224(2) Uani 1 1 d . . . . .
Cl3 Cl 0.8502(2) 0.02110(13) 0.35949(8) 0.0443(4) Uani 1 1 d . . . . .
O3 O 0.2567(5) 0.8721(3) -0.04032(16) 0.0214(7) Uani 1 1 d D . . . .
H22 H 0.190(6) 0.822(3) -0.062(2) 0.032 Uiso 1 1 d D U . . .
O4 O 0.4620(5) 0.7252(3) 0.04736(17) 0.0204(6) Uani 1 1 d D . . . .
H26 H 0.547(5) 0.670(5) 0.032(3) 0.031 Uiso 1 1 d D U . . .
H24 H 0.385(5) 0.762(4) 0.0181(19) 0.031 Uiso 1 1 d D U . . .
H4 H 0.493(7) 0.778(5) 0.075(2) 0.031 Uiso 1 1 d D U . . .
O5 O 0.7325(5) 0.5613(4) 0.00803(19) 0.0286(8) Uani 1 1 d D . . . .
H25 H 0.820(6) 0.603(6) -0.020(2) 0.043 Uiso 1 1 d D U . . .
H5 H 0.792(7) 0.500(5) 0.038(2) 0.043 Uiso 1 1 d D U . . .
H23 H 0.322(6) 0.945(4) -0.062(2) 0.043 Uiso 1 1 d D U . . .


_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 O1 1.448(6) . ?
C1 H1 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
O1 C2 1.354(5) . ?
C2 C3 1.361(6) . ?
C2 C19 1.452(6) . ?
C3 C4 1.413(6) . ?
C3 H3 0.9500 . ?
C4 N1 1.360(5) . ?
C4 C17 1.425(6) . ?
N1 C5 1.324(5) . ?
C5 C11 1.423(6) . ?
C5 C6 1.494(5) . ?
C6 N2 1.338(5) . ?
C6 C10 1.392(6) . ?
N2 C7 1.342(5) . ?
N2 H2 0.97(5) . ?
C7 C8 1.377(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N4 1.322(5) . ?
C11 C12 1.484(6) . ?
C12 N3 1.347(5) . ?
C12 C16 1.387(6) . ?
N3 C13 1.344(6) . ?
N3 H21 0.93(5) . ?
C13 C14 1.380(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N4 C17 1.356(5) . ?
C17 C18 1.414(6) . ?
C18 C19 1.366(6) . ?
C18 H18 0.9500 . ?
C19 O2 1.353(5) . ?
O2 C20 1.443(6) . ?
C20 H20 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
O3 H22 0.866(17) . ?
O3 H23 0.867(17) . ?
O4 H26 0.845(19) . ?
O4 H24 0.816(15) . ?
O4 H4 0.840(18) . ?
O5 H25 0.848(19) . ?
O5 H5 0.843(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1 109.5 . . ?
O1 C1 H1A 109.5 . . ?
H1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 O1 C1 115.8(4) . . ?
O1 C2 C3 125.3(4) . . ?
O1 C2 C19 113.7(4) . . ?
C3 C2 C19 121.0(4) . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N1 C4 C3 119.9(4) . . ?
N1 C4 C17 120.0(4) . . ?
C3 C4 C17 120.1(4) . . ?
C5 N1 C4 118.2(3) . . ?
N1 C5 C11 121.3(4) . . ?
N1 C5 C6 112.1(3) . . ?
C11 C5 C6 126.4(4) . . ?
N2 C6 C10 119.0(4) . . ?
N2 C6 C5 116.0(3) . . ?
C10 C6 C5 124.7(4) . . ?
C6 N2 C7 123.3(4) . . ?
C6 N2 H2 123(3) . . ?
C7 N2 H2 113(3) . . ?
N2 C7 C8 120.0(4) . . ?
N2 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 118.2(4) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C6 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C6 C10 H10 120.5 . . ?
N4 C11 C5 120.3(4) . . ?
N4 C11 C12 114.3(4) . . ?
C5 C11 C12 125.3(4) . . ?
N3 C12 C16 118.0(4) . . ?
N3 C12 C11 115.5(4) . . ?
C16 C12 C11 126.4(4) . . ?
C13 N3 C12 123.6(4) . . ?
C13 N3 H21 117(3) . . ?
C12 N3 H21 119(3) . . ?
N3 C13 C14 119.7(4) . . ?
N3 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 118.5(4) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C12 C16 C15 119.7(4) . . ?
C12 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C11 N4 C17 119.1(4) . . ?
N4 C17 C18 119.9(4) . . ?
N4 C17 C4 119.8(4) . . ?
C18 C17 C4 120.3(4) . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
O2 C19 C18 125.7(4) . . ?
O2 C19 C2 113.7(4) . . ?
C18 C19 C2 120.6(4) . . ?
C19 O2 C20 116.5(4) . . ?
O2 C20 H20 109.5 . . ?
O2 C20 H20A 109.5 . . ?
H20 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H22 O3 H23 126(3) . . ?
H26 O4 H24 115(3) . . ?
H26 O4 H4 118(5) . . ?
H24 O4 H4 116(3) . . ?
H25 O5 H5 103(3) . . ?

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 O1 C2 C3 4.4(6) . . . . ?
C1 O1 C2 C19 -178.2(4) . . . . ?
O1 C2 C3 C4 177.8(4) . . . . ?
C19 C2 C3 C4 0.6(6) . . . . ?
C2 C3 C4 N1 -174.1(4) . . . . ?
C2 C3 C4 C17 3.7(6) . . . . ?
C3 C4 N1 C5 -177.6(4) . . . . ?
C17 C4 N1 C5 4.6(6) . . . . ?
C4 N1 C5 C11 5.9(6) . . . . ?
C4 N1 C5 C6 -170.2(3) . . . . ?
N1 C5 C6 N2 -39.2(5) . . . . ?
C11 C5 C6 N2 144.9(4) . . . . ?
N1 C5 C6 C10 134.0(4) . . . . ?
C11 C5 C6 C10 -41.9(6) . . . . ?
C10 C6 N2 C7 0.8(6) . . . . ?
C5 C6 N2 C7 174.4(4) . . . . ?
C6 N2 C7 C8 -1.7(6) . . . . ?
N2 C7 C8 C9 1.4(6) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C8 C9 C10 C6 -0.6(6) . . . . ?
N2 C6 C10 C9 0.4(6) . . . . ?
C5 C6 C10 C9 -172.6(4) . . . . ?
N1 C5 C11 N4 -11.1(6) . . . . ?
C6 C5 C11 N4 164.5(4) . . . . ?
N1 C5 C11 C12 164.6(4) . . . . ?
C6 C5 C11 C12 -19.9(6) . . . . ?
N4 C11 C12 N3 -20.5(5) . . . . ?
C5 C11 C12 N3 163.6(4) . . . . ?
N4 C11 C12 C16 154.8(4) . . . . ?
C5 C11 C12 C16 -21.1(6) . . . . ?
C16 C12 N3 C13 2.4(6) . . . . ?
C11 C12 N3 C13 178.2(4) . . . . ?
C12 N3 C13 C14 -1.0(6) . . . . ?
N3 C13 C14 C15 -0.7(7) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
N3 C12 C16 C15 -2.2(6) . . . . ?
C11 C12 C16 C15 -177.4(4) . . . . ?
C14 C15 C16 C12 0.6(7) . . . . ?
C5 C11 N4 C17 4.7(6) . . . . ?
C12 C11 N4 C17 -171.4(3) . . . . ?
C11 N4 C17 C18 -177.0(4) . . . . ?
C11 N4 C17 C4 5.7(5) . . . . ?
N1 C4 C17 N4 -10.8(6) . . . . ?
C3 C4 C17 N4 171.5(4) . . . . ?
N1 C4 C17 C18 172.0(4) . . . . ?
C3 C4 C17 C18 -5.8(6) . . . . ?
N4 C17 C18 C19 -173.9(4) . . . . ?
C4 C17 C18 C19 3.3(6) . . . . ?
C17 C18 C19 O2 179.6(4) . . . . ?
C17 C18 C19 C2 1.0(6) . . . . ?
O1 C2 C19 O2 0.7(5) . . . . ?
C3 C2 C19 O2 178.2(4) . . . . ?
O1 C2 C19 C18 179.5(4) . . . . ?
C3 C2 C19 C18 -3.1(6) . . . . ?
C18 C19 O2 C20 4.2(6) . . . . ?
C2 C19 O2 C20 -177.1(4) . . . . ?

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
C1 H1A Cl1 0.98 2.78 3.687(5) 154.5 2_666 yes
N2 H2 Cl3 0.97(5) 2.06(5) 3.002(4) 162(4) . yes
C7 H7 Cl1 0.95 2.71 3.468(4) 136.9 1_545 yes
N3 H21 Cl3 0.93(5) 2.18(5) 3.046(4) 154(4) 1_565 yes
C16 H16 Cl2 0.95 2.72 3.571(4) 149.0 2_665 yes
O3 H22 Cl2 0.866(17) 2.169(18) 3.032(3) 176(3) . yes
O4 H26 O5 0.845(19) 1.696(19) 2.538(5) 174(5) . yes
O4 H24 O3 0.816(15) 1.641(19) 2.441(4) 166(4) . yes
O4 H4 Cl1 0.840(18) 2.09(2) 2.925(3) 170(5) . yes
O5 H25 Cl2 0.848(19) 2.27(2) 3.107(4) 168(6) 1_655 yes
O5 H5 Cl2 0.843(19) 2.32(2) 3.163(4) 175(6) 2_665 yes
O3 H23 Cl1 0.867(17) 2.20(3) 3.022(3) 159(4) 2_675 yes

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.106



_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_chemical_absolute_configuration ?
