# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_AP-BIN-8
_database_code_depnum_ccdc_archive 'CCDC 1438715'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_audit_creation_date             2015-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C20 H15 Cl N4 O6'
_chemical_formula_sum            'C20 H15 Cl N4 O6'
_chemical_formula_weight         442.82
_chemical_oxdiff_formula         C20H15ClN4O6
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.4898(8)
_cell_length_b                   8.3928(8)
_cell_length_c                   20.0409(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.127(8)
_cell_angle_gamma                90
_cell_volume                     1927.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2511
_cell_measurement_temperature    295.2(8)
_cell_measurement_theta_max      27.1650
_cell_measurement_theta_min      3.5990
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5258
_exptl_crystal_F_000             913.0896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9774
_diffrn_reflns_theta_full        28.8276
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      295.2(8)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.8702
_diffrn_measured_fraction_theta_max 0.8695
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   31.00   1.0000   17.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   -6.0000   -5.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00  -69.00   1.0000   17.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   -6.0000   -5.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   89.00   1.0000   17.0500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   77.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   47.00   93.00   1.0000   17.0500
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -41.00   55.00   1.0000   17.0500
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -77.0000   30.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0422586000
_diffrn_orient_matrix_UB_12      -0.0004077000
_diffrn_orient_matrix_UB_13      0.0241153000
_diffrn_orient_matrix_UB_21      0.0450726000
_diffrn_orient_matrix_UB_22      -0.0063680000
_diffrn_orient_matrix_UB_23      0.0259598000
_diffrn_orient_matrix_UB_31      0.0031678000
_diffrn_orient_matrix_UB_32      0.0842908000
_diffrn_orient_matrix_UB_33      0.0020585000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -15
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              -11
_reflns_number_gt                3038
_reflns_number_total             4397
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.4352
_refine_diff_density_min         -0.3948
_refine_diff_density_rms         0.0803
_refine_ls_d_res_high            0.7370
_refine_ls_d_res_low             6.4977
_refine_ls_goodness_of_fit_ref   1.1130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.1130
_refine_ls_shift/su_max          0.0031
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1889
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b)
2.c Aromatic/amide H refined with riding coordinates:
 C1d(H1d), C1g(H1g), C10(H10), C29(H29), C1h(H1h), C1j(H1j), C1f(H1f)
2.d X=CH2 refined with riding coordinates:
 N4(H4a,H4b)
2.e Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Cl1 Cl 0.12283(6) 0.62553(10) 0.36923(4) 0.0712(3) Uani 1.000000 .
O5 O -0.19238(15) 0.8680(2) 0.60241(9) 0.0507(5) Uani 1.000000 .
N2 N -0.34878(16) 0.8126(2) 0.53389(9) 0.0385(5) Uani 1.000000 .
O1 O -0.35815(17) 1.0425(2) 0.34403(9) 0.0559(5) Uani 1.000000 .
N3 N -0.46139(16) 0.7471(2) 0.52135(9) 0.0382(5) Uani 1.000000 .
C5 C -0.3350(2) 0.6904(3) 0.64223(11) 0.0376(5) Uani 1.000000 .
N4 N -0.61268(18) 0.7589(3) 0.43523(12) 0.0557(6) Uani 1.000000 .
O6 O -0.60747(17) 0.5879(3) 0.54932(12) 0.0697(6) Uani 1.000000 .
N1 N -0.0864(2) 0.4295(3) 0.41307(12) 0.0512(6) Uani 1.000000 .
C9 C -0.2851(2) 0.7976(3) 0.59314(11) 0.0372(5) Uani 1.000000 .
C10 C -0.19187(19) 0.6665(3) 0.44264(11) 0.0354(5) Uani 1.000000 .
C11 C -0.5109(2) 0.6469(3) 0.56475(14) 0.0462(6) Uani 1.000000 .
O3 O -0.1190(2) 0.3520(3) 0.46020(13) 0.0844(8) Uani 1.000000 .
C13 C -0.3131(2) 0.9010(3) 0.47478(11) 0.0352(5) Uani 1.000000 .
C14 C -0.20388(19) 0.8305(3) 0.44836(10) 0.0320(5) Uani 1.000000 .
O2 O -0.53840(18) 0.9387(3) 0.32984(10) 0.0706(6) Uani 1.000000 .
C16 C -0.4433(2) 0.6183(3) 0.62794(12) 0.0409(6) Uani 1.000000 .
C17 C -0.09332(19) 0.6038(3) 0.41763(11) 0.0360(5) Uani 1.000000 .
C18 C -0.4231(2) 0.8866(3) 0.42896(12) 0.0407(6) Uani 1.000000 .
C19 C -0.4468(2) 0.9566(3) 0.36357(13) 0.0485(6) Uani 1.000000 .
C25 C -0.0038(2) 0.7011(3) 0.39860(12) 0.0422(6) Uani 1.000000 .
C1b C -0.5040(2) 0.7980(3) 0.45752(12) 0.0398(6) Uani 1.000000 .
O4 O -0.0513(3) 0.3689(3) 0.36335(14) 0.0907(8) Uani 1.000000 .
C1d C -0.0149(2) 0.8639(3) 0.40544(13) 0.0475(6) Uani 1.000000 .
C29 C -0.2718(2) 0.6582(3) 0.70253(13) 0.0504(7) Uani 1.000000 .
C1f C -0.4875(3) 0.5151(3) 0.67499(15) 0.0565(7) Uani 1.000000 .
C1g C -0.1145(2) 0.9276(3) 0.43010(12) 0.0426(6) Uani 1.000000 .
C1h C -0.3170(3) 0.5571(3) 0.74831(14) 0.0565(7) Uani 1.000000 .
C28 C -0.3730(3) 1.1078(4) 0.27695(15) 0.0696(9) Uani 1.000000 .
C1j C -0.4241(3) 0.4864(3) 0.73452(15) 0.0592(8) Uani 1.000000 .
C27 C -0.2653(4) 1.1848(7) 0.2613(2) 0.1199(19) Uani 1.000000 .
H1d H 0.0446(2) 0.9310(3) 0.39349(13) 0.0570(8) Uiso 1.000000 R
H1g H -0.1212(2) 1.0375(3) 0.43442(12) 0.0511(7) Uiso 1.000000 R
H10 H -0.25036(19) 0.5991(3) 0.45570(11) 0.0425(6) Uiso 1.000000 R
H29 H -0.1990(2) 0.7048(3) 0.71195(13) 0.0605(8) Uiso 1.000000 R
H1h H -0.2749(3) 0.5366(3) 0.78878(14) 0.0678(9) Uiso 1.000000 R
H1j H -0.4538(3) 0.4186(3) 0.76580(15) 0.0711(9) Uiso 1.000000 R
H1f H -0.5595(3) 0.4661(3) 0.66590(15) 0.0678(9) Uiso 1.000000 R
H4a H -0.65547(18) 0.7033(3) 0.45994(12) 0.0668(7) Uiso 1.000000 R
H4b H -0.63983(18) 0.7893(3) 0.39619(12) 0.0668(7) Uiso 1.000000 R
H13 H -0.2994(2) 1.0131(3) 0.48661(11) 0.0422(6) Uiso 1.000000 R
H28a H -0.3921(3) 1.0232(4) 0.24504(15) 0.0835(11) Uiso 1.000000 R
H28b H -0.4363(3) 1.1844(4) 0.27421(15) 0.0835(11) Uiso 1.000000 R
H27a H -0.2743(12) 1.228(4) 0.2170(8) 0.180(3) Uiso 1.000000 GR
H27b H -0.2474(18) 1.269(3) 0.2928(12) 0.180(3) Uiso 1.000000 GR
H27c H -0.2031(8) 1.1083(11) 0.2639(19) 0.180(3) Uiso 1.000000 GR


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 C25 1.729(2) . ?
O5 C9 1.220(3) . ?
N2 N3 1.411(2) . ?
N2 C9 1.355(3) . ?
N2 C13 1.481(3) . ?
O1 C19 1.330(3) . ?
O1 C28 1.450(3) . ?
N3 C11 1.364(3) . ?
N3 C1b 1.403(3) . ?
C5 C9 1.479(3) . ?
C5 C16 1.394(3) . ?
C5 C29 1.391(4) . ?
N4 C1b 1.337(3) . ?
O6 C11 1.234(3) . ?
N1 O3 1.227(3) . ?
N1 C17 1.469(3) . ?
N1 O4 1.213(3) . ?
C10 C14 1.389(3) . ?
C10 C17 1.375(3) . ?
C11 C16 1.457(4) . ?
C13 C14 1.517(3) . ?
C13 C18 1.513(3) . ?
C14 C1g 1.381(3) . ?
O2 C19 1.218(3) . ?
C16 C1f 1.402(3) . ?
C17 C25 1.388(3) . ?
C18 C19 1.444(4) . ?
C18 C1b 1.349(3) . ?
C25 C1d 1.380(3) . ?
C1d C1g 1.386(4) . ?
C29 C1h 1.379(4) . ?
C1f C1j 1.373(4) . ?
C1h C1j 1.376(4) . ?
C28 C27 1.449(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 N3 123.40(19) . . ?
C13 N2 N3 110.82(17) . . ?
C13 N2 C9 125.76(18) . . ?
C28 O1 C19 115.9(2) . . ?
C11 N3 N2 123.06(19) . . ?
C1b N3 N2 107.41(18) . . ?
C1b N3 C11 129.4(2) . . ?
C16 C5 C9 120.7(2) . . ?
C29 C5 C9 119.5(2) . . ?
C29 C5 C16 119.8(2) . . ?
C17 N1 O3 117.3(2) . . ?
O4 N1 O3 123.2(3) . . ?
O4 N1 C17 119.4(3) . . ?
N2 C9 O5 119.9(2) . . ?
C5 C9 O5 124.7(2) . . ?
C5 C9 N2 115.4(2) . . ?
C17 C10 C14 119.9(2) . . ?
O6 C11 N3 119.8(3) . . ?
C16 C11 N3 115.8(2) . . ?
C16 C11 O6 124.4(3) . . ?
C14 C13 N2 111.53(18) . . ?
C18 C13 N2 100.27(18) . . ?
C18 C13 C14 115.65(19) . . ?
C13 C14 C10 120.35(19) . . ?
C1g C14 C10 118.9(2) . . ?
C1g C14 C13 120.8(2) . . ?
C11 C16 C5 121.3(2) . . ?
C1f C16 C5 119.4(2) . . ?
C1f C16 C11 119.3(2) . . ?
C10 C17 N1 117.0(2) . . ?
C25 C17 N1 121.6(2) . . ?
C25 C17 C10 121.4(2) . . ?
C19 C18 C13 127.8(2) . . ?
C1b C18 C13 110.9(2) . . ?
C1b C18 C19 121.3(2) . . ?
O2 C19 O1 123.6(3) . . ?
C18 C19 O1 112.9(2) . . ?
C18 C19 O2 123.5(3) . . ?
C17 C25 Cl1 122.4(2) . . ?
C1d C25 Cl1 118.87(19) . . ?
C1d C25 C17 118.7(2) . . ?
N4 C1b N3 119.1(2) . . ?
C18 C1b N3 110.4(2) . . ?
C18 C1b N4 130.5(2) . . ?
C1g C1d C25 120.1(2) . . ?
C1h C29 C5 119.9(3) . . ?
C1j C1f C16 119.8(3) . . ?
C1d C1g C14 121.0(2) . . ?
C1j C1h C29 120.4(3) . . ?
C27 C28 O1 108.9(3) . . ?
C1h C1j C1f 120.6(3) . . ?

_chemical_name_systematic        AP-BIN-8
