# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_bl-17
_database_code_depnum_ccdc_archive 'CCDC 1449631'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2016-01-13
_chemical_formula_sum            'C6 H17 N17 O5'
_chemical_formula_weight         407.370
_refine_ls_R_factor_all          0.084
_cell_length_a                   9.771(2)
_cell_length_b                   7.0600(14)
_cell_length_c                   23.868(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 97.28(3)
_cell_angle_gamma                90.000
_cell_volume                     1633.2(6)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P_2ybc

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? ?
N ? ?
H ? ?
C ? ?


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 1.2003(2) 0.5935(4) 0.3739(1) 1.000 4 e ? d Uani 0.0258(5)
O4 O 0.6143(2) 1.0010(4) 0.3087(1) 1.000 4 e ? d Uani 0.0253(5)
O2 O 1.1209(2) 0.5469(4) 0.4541(1) 1.000 4 e ? d Uani 0.0315(6)
O3 O 0.7571(2) 0.9776(3) 0.2464(1) 1.000 4 e ? d Uani 0.0221(5)
N10 N 0.7483(3) 0.3096(4) 0.4159(1) 1.000 4 e ? d Uani 0.0247(6)
H10A H 0.8017 0.3924 0.4357 1.000 4 e ? d Uiso 0.03000
H10B H 0.7803 0.1939 0.4132 1.000 4 e ? d Uiso 0.03000
N3 N 1.1088(2) 0.6090(4) 0.4056(1) 1.000 4 e ? d Uani 0.0194(5)
N7 N 0.8123(3) 0.6058(4) 0.1574(1) 1.000 4 e ? d Uani 0.0223(6)
N2 N 0.7885(2) 0.8412(4) 0.3884(1) 1.000 4 e ? d Uani 0.0198(5)
N1 N 0.8930(3) 0.7535(4) 0.4191(1) 1.000 4 e ? d Uani 0.0215(6)
N9 N 1.0126(2) 0.7381(4) 0.1825(1) 1.000 4 e ? d Uani 0.0197(5)
N8 N 0.9229(3) 0.6757(4) 0.1386(1) 1.000 4 e ? d Uani 0.0232(6)
N4 N 0.7261(2) 0.9453(4) 0.2940(1) 1.000 4 e ? d Uani 0.0172(5)
N6 N 0.8275(3) 0.6162(4) 0.2141(1) 1.000 4 e ? d Uani 0.0204(5)
N11 N 0.7407(2) 0.3786(4) 0.3598(1) 1.000 4 e ? d Uani 0.0215(6)
H11 H 0.8159 0.3900 0.3433 1.000 4 e ? calc Uiso 0.02600
N5 N 1.0125(2) 0.7295(4) 0.2824(1) 1.000 4 e ? d Uani 0.0193(5)
H5 H 1.0999 0.6962 0.2886 1.000 4 e ? d Uiso 0.02300
N13 N 0.5044(3) 0.4138(4) 0.3570(1) 1.000 4 e ? d Uani 0.0259(6)
H13A H 0.4242 0.4462 0.3384 1.000 4 e ? calc Uiso 0.03100
H13B H 0.5094 0.3731 0.3920 1.000 4 e ? calc Uiso 0.03100
N12 N 0.6122(3) 0.4873(5) 0.2795(1) 1.000 4 e ? d Uani 0.0315(7)
H12A H 0.5326 0.5201 0.2605 1.000 4 e ? calc Uiso 0.03800
H12B H 0.6883 0.4950 0.2635 1.000 4 e ? calc Uiso 0.03800
C1 C 0.9855(3) 0.7038(4) 0.3839(1) 1.000 4 e ? d Uani 0.0166(6)
C2 C 0.9437(3) 0.7580(4) 0.3278(1) 1.000 4 e ? d Uani 0.0158(6)
C4 C 0.9504(3) 0.6978(4) 0.2274(1) 1.000 4 e ? d Uani 0.0164(6)
C5 C 0.6173(3) 0.4264(5) 0.3322(1) 1.000 4 e ? d Uani 0.0213(6)
C3 C 0.8163(3) 0.8445(4) 0.3335(1) 1.000 4 e ? d Uani 0.0167(6)
O5 O 0.1351(2) 0.0728(4) 0.4736(1) 1.000 4 e ? d Uani 0.0280(6)
H5A H 0.0848 0.1139 0.4450 1.000 4 e ? d Uiso 0.03400
H5B H 0.0998 0.1326 0.4986 1.000 4 e ? d Uiso 0.03400
N14 N 0.3961(3) 0.3282(4) 0.4796(1) 1.000 4 e ? d Uani 0.0267(6)
H14A H 0.3250 0.2721 0.4615 1.000 4 e ? d Uiso 0.03200
H14B H 0.3806 0.4490 0.4798 1.000 4 e ? d Uiso 0.03200
N17 N 0.5524(3) 0.0767(4) 0.6011(1) 1.000 4 e ? d Uani 0.0285(7)
H17A H 0.6293 0.0152 0.6124 1.000 4 e ? calc Uiso 0.03400
H17B H 0.4853 0.0787 0.6224 1.000 4 e ? calc Uiso 0.03400
N16 N 0.6365(2) 0.1656(4) 0.5190(1) 1.000 4 e ? d Uani 0.0227(6)
H16A H 0.7142 0.1050 0.5296 1.000 4 e ? calc Uiso 0.02700
H16B H 0.6247 0.2258 0.4865 1.000 4 e ? calc Uiso 0.02700
N15 N 0.4205(3) 0.2599(4) 0.5356(1) 1.000 4 e ? d Uani 0.0235(6)
H15 H 0.3597 0.2788 0.5593 1.000 4 e ? calc Uiso 0.02800
C6 C 0.5377(3) 0.1660(4) 0.5519(1) 1.000 4 e ? d Uani 0.0199(6)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N3 . . 1.247(3) no
O4 N4 . . 1.252(3) no
O2 N3 . . 1.229(3) no
O3 N4 . . 1.234(3) no
N10 N11 . . 1.418(3) no
N10 H10A . . 0.8801 no
N10 H10B . . 0.8798 no
N3 C1 . . 1.417(4) no
N7 N8 . . 1.317(4) no
N7 N6 . . 1.347(3) no
N2 N1 . . 1.332(4) no
N2 C3 . . 1.373(4) no
N1 C1 . . 1.356(4) no
N9 C4 . . 1.329(4) no
N9 N8 . . 1.351(4) no
N4 C3 . . 1.400(4) no
N6 C4 . . 1.333(4) no
N11 C5 . . 1.342(4) no
N11 H11 . . 0.8800 no
N5 C2 . . 1.360(4) no
N5 C4 . . 1.394(4) no
N5 H5 . . 0.8800 no
N13 C5 . . 1.319(4) no
N13 H13A . . 0.8800 no
N13 H13B . . 0.8800 no
N12 C5 . . 1.323(4) no
N12 H12A . . 0.8800 no
N12 H12B . . 0.8800 no
C1 C2 . . 1.403(4) no
C2 C3 . . 1.409(4) no
O5 H5A . . 0.8399 no
O5 H5B . . 0.8401 no
N14 N15 . . 1.411(4) no
N14 H14A . . 0.8667 no
N14 H14B . . 0.8662 no
N17 C6 . . 1.324(4) no
N17 H17A . . 0.8800 no
N17 H17B . . 0.8800 no
N16 C6 . . 1.319(4) no
N16 H16A . . 0.8800 no
N16 H16B . . 0.8800 no
N15 C6 . . 1.339(4) no
N15 H15 . . 0.8800 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N11 N10 H10A . . . 103.70 no
N11 N10 H10B . . . 103.10 no
H10A N10 H10B . . . 117.70 no
O2 N3 O1 . . . 123.3(3) no
O2 N3 C1 . . . 119.2(2) no
O1 N3 C1 . . . 117.4(2) no
N8 N7 N6 . . . 109.3(2) no
N1 N2 C3 . . . 107.6(2) no
N2 N1 C1 . . . 107.7(2) no
C4 N9 N8 . . . 103.7(2) no
N7 N8 N9 . . . 109.8(2) no
O3 N4 O4 . . . 121.6(2) no
O3 N4 C3 . . . 120.5(2) no
O4 N4 C3 . . . 117.9(2) no
C4 N6 N7 . . . 104.1(2) no
C5 N11 N10 . . . 119.1(2) no
C5 N11 H11 . . . 120.40 no
N10 N11 H11 . . . 120.40 no
C2 N5 C4 . . . 125.1(2) no
C2 N5 H5 . . . 118.20 no
C4 N5 H5 . . . 114.40 no
C5 N13 H13A . . . 120.00 no
C5 N13 H13B . . . 120.00 no
H13A N13 H13B . . . 120.00 no
C5 N12 H12A . . . 120.00 no
C5 N12 H12B . . . 120.00 no
H12A N12 H12B . . . 120.00 no
N1 C1 C2 . . . 112.6(2) no
N1 C1 N3 . . . 119.9(3) no
C2 C1 N3 . . . 127.5(3) no
N5 C2 C1 . . . 127.3(3) no
N5 C2 C3 . . . 132.3(3) no
C1 C2 C3 . . . 100.4(2) no
N9 C4 N6 . . . 113.1(3) no
N9 C4 N5 . . . 122.5(3) no
N6 C4 N5 . . . 124.4(3) no
N13 C5 N12 . . . 121.0(3) no
N13 C5 N11 . . . 120.9(3) no
N12 C5 N11 . . . 118.1(3) no
N2 C3 N4 . . . 117.9(2) no
N2 C3 C2 . . . 111.6(2) no
N4 C3 C2 . . . 130.1(3) no
H5A O5 H5B . . . 98.80 no
N15 N14 H14A . . . 110.20 no
N15 N14 H14B . . . 109.90 no
H14A N14 H14B . . . 108.80 no
C6 N17 H17A . . . 120.00 no
C6 N17 H17B . . . 120.00 no
H17A N17 H17B . . . 120.00 no
C6 N16 H16A . . . 120.00 no
C6 N16 H16B . . . 120.00 no
H16A N16 H16B . . . 120.00 no
C6 N15 N14 . . . 118.7(2) no
C6 N15 H15 . . . 120.60 no
N14 N15 H15 . . . 120.60 no
N16 C6 N17 . . . 121.4(3) no
N16 C6 N15 . . . 119.4(3) no
N17 C6 N15 . . . 119.1(3) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N2 N1 C1 . . . . 0.5(3) no
N6 N7 N8 N9 . . . . -1.4(3) no
C4 N9 N8 N7 . . . . 1.2(3) no
N8 N7 N6 C4 . . . . 1.0(3) no
N2 N1 C1 C2 . . . . -0.2(4) no
N2 N1 C1 N3 . . . . 179.4(3) no
O2 N3 C1 N1 . . . . 11.1(4) no
O1 N3 C1 N1 . . . . -168.7(3) no
O2 N3 C1 C2 . . . . -169.4(3) no
O1 N3 C1 C2 . . . . 10.8(4) no
C4 N5 C2 C1 . . . . 147.2(3) no
C4 N5 C2 C3 . . . . -32.5(5) no
N1 C1 C2 N5 . . . . -180.0(3) no
N3 C1 C2 N5 . . . . 0.5(5) no
N1 C1 C2 C3 . . . . -0.2(3) no
N3 C1 C2 C3 . . . . -179.7(3) no
N8 N9 C4 N6 . . . . -0.6(3) no
N8 N9 C4 N5 . . . . 176.2(3) no
N7 N6 C4 N9 . . . . -0.2(3) no
N7 N6 C4 N5 . . . . -176.9(3) no
C2 N5 C4 N9 . . . . 154.9(3) no
C2 N5 C4 N6 . . . . -28.7(5) no
N10 N11 C5 N13 . . . . 1.5(5) no
N10 N11 C5 N12 . . . . -178.8(3) no
N1 N2 C3 N4 . . . . -174.4(3) no
N1 N2 C3 C2 . . . . -0.7(3) no
O3 N4 C3 N2 . . . . 168.8(3) no
O4 N4 C3 N2 . . . . -11.2(4) no
O3 N4 C3 C2 . . . . -3.6(5) no
O4 N4 C3 C2 . . . . 176.5(3) no
N5 C2 C3 N2 . . . . -179.7(3) no
C1 C2 C3 N2 . . . . 0.5(3) no
N5 C2 C3 N4 . . . . -7.0(6) no
C1 C2 C3 N4 . . . . 173.2(3) no
N14 N15 C6 N16 . . . . 10.8(4) no
N14 N15 C6 N17 . . . . -169.7(3) no
####################################################################### 
# 
# 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_bl75a
_database_code_depnum_ccdc_archive 'CCDC 1449632'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H2 K N9 O6'
_chemical_formula_weight         323.26

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.8823(18)
_cell_length_b                   10.952(2)
_cell_length_c                   11.675(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.38(3)
_cell_angle_gamma                90.00
_cell_volume                     1083.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3459
_cell_measurement_theta_min      1.8277
_cell_measurement_theta_max      27.4121

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5582
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1868
_reflns_number_gt                1749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0986P)²+1.9404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1855
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_restrained_S_all      1.273
_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
K1 K 0.23398(13) 0.75783(9) 0.17701(10) 0.0339(4) Uani 1 1 d . . .
O1 O 0.4493(4) 0.9772(3) 0.2322(3) 0.0307(8) Uani 1 1 d . . .
O2 O 0.4372(4) 1.1723(3) 0.2650(3) 0.0293(8) Uani 1 1 d . . .
O3 O 0.0929(4) 1.6264(3) 0.3836(3) 0.0311(8) Uani 1 1 d . . .
O4 O -0.0972(4) 1.4941(3) 0.3578(3) 0.0261(7) Uani 1 1 d . . .
O5 O 0.1477(5) 1.1796(3) 0.6354(3) 0.0366(9) Uani 1 1 d . . .
O6 O 0.1116(4) 0.9861(3) 0.6604(3) 0.0296(8) Uani 1 1 d . . .
N1 N 0.4118(4) 1.0649(3) 0.2837(3) 0.0220(8) Uani 1 1 d . . .
N2 N 0.3226(4) 0.9233(3) 0.4077(3) 0.0213(8) Uani 1 1 d . . .
N3 N 0.2535(4) 0.9259(3) 0.4966(3) 0.0210(8) Uani 1 1 d . . .
N4 N 0.1575(4) 1.0724(3) 0.6108(3) 0.0230(8) Uani 1 1 d . . .
N5 N 0.2608(4) 1.2514(3) 0.4336(3) 0.0161(8) Uani 1 1 d . . .
N6 N 0.1130(4) 1.3081(3) 0.3993(3) 0.0174(8) Uani 1 1 d . . .
N7 N 0.3131(4) 1.4498(3) 0.4423(3) 0.0221(8) Uani 1 1 d . . .
N8 N 0.0433(5) 1.5214(3) 0.3806(3) 0.0230(8) Uani 1 1 d . . .
N9 N 0.5315(4) 1.3132(3) 0.4990(3) 0.0223(8) Uani 1 1 d . . .
H9A H 0.5727 1.2442 0.5353 0.027 Uiso 1 1 d R . .
H9B H 0.5955 1.3770 0.5224 0.027 Uiso 1 1 d R . .
C1 C 0.3363(5) 1.0411(4) 0.3745(3) 0.0182(9) Uani 1 1 d . . .
C2 C 0.2754(5) 1.1233(4) 0.4409(3) 0.0190(9) Uani 1 1 d . . .
C3 C 0.2269(5) 1.0433(4) 0.5170(4) 0.0177(9) Uani 1 1 d . . .
C4 C 0.3772(5) 1.3383(4) 0.4603(3) 0.0189(9) Uani 1 1 d . . .
C5 C 0.1583(5) 1.4230(4) 0.4071(3) 0.0170(9) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O4 2.836(3) 2_545 ?
K1 O6 2.869(3) 4_575 ?
K1 O2 2.947(4) 2_645 ?
K1 N3 2.955(4) 4_575 ?
K1 N6 2.993(4) 2_545 ?
K1 O1 3.018(4) . ?
K1 N2 3.145(4) . ?
K1 O3 3.356(3) 1_545 ?
K1 N9 3.389(4) 2_645 ?
O1 N1 1.231(5) . ?
O2 N1 1.230(5) . ?
O2 K1 2.947(4) 2_655 ?
O3 N8 1.228(5) . ?
O3 K1 3.356(3) 1_565 ?
O4 N8 1.233(5) . ?
O4 K1 2.836(3) 2 ?
O5 N4 1.219(5) . ?
O6 N4 1.239(5) . ?
O6 K1 2.869(3) 4_576 ?
N1 C1 1.437(5) . ?
N2 N3 1.355(5) . ?
N2 C1 1.364(5) . ?
N3 C3 1.341(5) . ?
N3 K1 2.955(4) 4_576 ?
N4 C3 1.443(5) . ?
N5 C4 1.371(5) . ?
N5 N6 1.398(5) . ?
N5 C2 1.410(5) . ?
N6 C5 1.316(6) . ?
N6 K1 2.993(4) 2 ?
N7 C4 1.337(6) . ?
N7 C5 1.345(6) . ?
N8 C5 1.453(6) . ?
N9 C4 1.337(6) . ?
N9 K1 3.389(4) 2_655 ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
C1 C2 1.398(6) . ?
C2 C3 1.404(6) . ?

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 K1 O6 134.63(10) 2_545 4_575 ?
O4 K1 O2 132.52(10) 2_545 2_645 ?
O6 K1 O2 92.81(10) 4_575 2_645 ?
O4 K1 N3 129.29(10) 2_545 4_575 ?
O6 K1 N3 54.50(9) 4_575 4_575 ?
O2 K1 N3 71.47(10) 2_645 4_575 ?
O4 K1 N6 55.28(9) 2_545 2_545 ?
O6 K1 N6 79.36(10) 4_575 2_545 ?
O2 K1 N6 171.40(10) 2_645 2_545 ?
N3 K1 N6 100.81(10) 4_575 2_545 ?
O4 K1 O1 61.40(9) 2_545 . ?
O6 K1 O1 163.51(10) 4_575 . ?
O2 K1 O1 71.50(9) 2_645 . ?
N3 K1 O1 121.73(10) 4_575 . ?
N6 K1 O1 116.60(10) 2_545 . ?
O4 K1 N2 65.42(9) 2_545 . ?
O6 K1 N2 125.97(10) 4_575 . ?
O2 K1 N2 90.51(10) 2_645 . ?
N3 K1 N2 161.74(11) 4_575 . ?
N6 K1 N2 96.96(10) 2_545 . ?
O1 K1 N2 51.54(9) . . ?
O4 K1 O3 104.97(9) 2_545 1_545 ?
O6 K1 O3 55.53(8) 4_575 1_545 ?
O2 K1 O3 104.81(9) 2_645 1_545 ?
N3 K1 O3 109.51(9) 4_575 1_545 ?
N6 K1 O3 73.76(9) 2_545 1_545 ?
O1 K1 O3 122.46(9) . 1_545 ?
N2 K1 O3 71.54(9) . 1_545 ?
O4 K1 N9 93.69(9) 2_545 2_645 ?
O6 K1 N9 114.51(9) 4_575 2_645 ?
O2 K1 N9 56.62(9) 2_645 2_645 ?
N3 K1 N9 60.82(9) 4_575 2_645 ?
N6 K1 N9 123.46(9) 2_545 2_645 ?
O1 K1 N9 61.43(9) . 2_645 ?
N2 K1 N9 111.97(10) . 2_645 ?
O3 K1 N9 160.31(9) 1_545 2_645 ?
N1 O1 K1 118.6(3) . . ?
N1 O2 K1 119.0(3) . 2_655 ?
N8 O3 K1 126.1(3) . 1_565 ?
N8 O4 K1 128.0(3) . 2 ?
N4 O6 K1 124.8(3) . 4_576 ?
O2 N1 O1 124.6(4) . . ?
O2 N1 C1 117.1(3) . . ?
O1 N1 C1 118.2(4) . . ?
N3 N2 C1 107.2(3) . . ?
N3 N2 K1 127.9(2) . . ?
C1 N2 K1 108.8(2) . . ?
C3 N3 N2 107.5(3) . . ?
C3 N3 K1 118.4(3) . 4_576 ?
N2 N3 K1 131.9(2) . 4_576 ?
O5 N4 O6 124.6(4) . . ?
O5 N4 C3 117.9(4) . . ?
O6 N4 C3 117.4(3) . . ?
C4 N5 N6 109.7(3) . . ?
C4 N5 C2 128.9(4) . . ?
N6 N5 C2 121.4(3) . . ?
C5 N6 N5 99.4(3) . . ?
C5 N6 K1 117.5(3) . 2 ?
N5 N6 K1 143.1(2) . 2 ?
C4 N7 C5 101.4(3) . . ?
O3 N8 O4 124.4(4) . . ?
O3 N8 C5 117.7(4) . . ?
O4 N8 C5 117.8(3) . . ?
C4 N9 K1 125.8(3) . 2_655 ?
C4 N9 H9A 124.7 . . ?
K1 N9 H9A 84.1 2_655 . ?
C4 N9 H9B 116.0 . . ?
K1 N9 H9B 82.8 2_655 . ?
H9A N9 H9B 112.7 . . ?
N2 C1 C2 111.7(4) . . ?
N2 C1 N1 118.8(4) . . ?
C2 C1 N1 129.5(4) . . ?
C1 C2 C3 101.1(3) . . ?
C1 C2 N5 130.6(4) . . ?
C3 C2 N5 128.3(4) . . ?
N3 C3 C2 112.5(4) . . ?
N3 C3 N4 118.9(4) . . ?
C2 C3 N4 128.6(4) . . ?
N7 C4 N9 125.9(4) . . ?
N7 C4 N5 110.0(4) . . ?
N9 C4 N5 124.1(4) . . ?
N6 C5 N7 119.5(4) . . ?
N6 C5 N8 120.9(4) . . ?
N7 C5 N8 119.5(4) . . ?

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
O4 K1 O1 N1 41.2(3) 2_545 . . . ?
O6 K1 O1 N1 -126.5(4) 4_575 . . . ?
O2 K1 O1 N1 -145.0(3) 2_645 . . . ?
N3 K1 O1 N1 162.0(3) 4_575 . . . ?
N6 K1 O1 N1 38.2(3) 2_545 . . . ?
N2 K1 O1 N1 -38.9(3) . . . . ?
O3 K1 O1 N1 -48.9(3) 1_545 . . . ?
N9 K1 O1 N1 153.6(3) 2_645 . . . ?
K1 O2 N1 O1 -64.5(5) 2_655 . . . ?
K1 O2 N1 C1 113.9(3) 2_655 . . . ?
K1 O1 N1 O2 -144.7(3) . . . . ?
K1 O1 N1 C1 36.9(4) . . . . ?
O4 K1 N2 N3 95.8(3) 2_545 . . . ?
O6 K1 N2 N3 -32.7(4) 4_575 . . . ?
O2 K1 N2 N3 -126.5(3) 2_645 . . . ?
N3 K1 N2 N3 -117.5(3) 4_575 . . . ?
N6 K1 N2 N3 49.2(3) 2_545 . . . ?
O1 K1 N2 N3 167.8(4) . . . . ?
O3 K1 N2 N3 -21.1(3) 1_545 . . . ?
N9 K1 N2 N3 179.6(3) 2_645 . . . ?
O4 K1 N2 C1 -35.7(3) 2_545 . . . ?
O6 K1 N2 C1 -164.2(3) 4_575 . . . ?
O2 K1 N2 C1 102.0(3) 2_645 . . . ?
N3 K1 N2 C1 111.0(4) 4_575 . . . ?
N6 K1 N2 C1 -82.3(3) 2_545 . . . ?
O1 K1 N2 C1 36.4(3) . . . . ?
O3 K1 N2 C1 -152.5(3) 1_545 . . . ?
N9 K1 N2 C1 48.1(3) 2_645 . . . ?
C1 N2 N3 C3 -0.3(5) . . . . ?
K1 N2 N3 C3 -132.3(3) . . . . ?
C1 N2 N3 K1 -162.6(3) . . . 4_576 ?
K1 N2 N3 K1 65.4(4) . . . 4_576 ?
K1 O6 N4 O5 -154.5(3) 4_576 . . . ?
K1 O6 N4 C3 25.8(5) 4_576 . . . ?
C4 N5 N6 C5 1.2(4) . . . . ?
C2 N5 N6 C5 179.1(3) . . . . ?
C4 N5 N6 K1 -178.6(3) . . . 2 ?
C2 N5 N6 K1 -0.7(6) . . . 2 ?
K1 O3 N8 O4 -106.3(4) 1_565 . . . ?
K1 O3 N8 C5 74.4(4) 1_565 . . . ?
K1 O4 N8 O3 172.9(3) 2 . . . ?
K1 O4 N8 C5 -7.8(5) 2 . . . ?
N3 N2 C1 C2 -0.4(5) . . . . ?
K1 N2 C1 C2 141.4(3) . . . . ?
N3 N2 C1 N1 177.8(3) . . . . ?
K1 N2 C1 N1 -40.5(4) . . . . ?
O2 N1 C1 N2 -172.5(4) . . . . ?
O1 N1 C1 N2 6.0(6) . . . . ?
O2 N1 C1 C2 5.2(6) . . . . ?
O1 N1 C1 C2 -176.3(4) . . . . ?
N2 C1 C2 C3 0.8(5) . . . . ?
N1 C1 C2 C3 -177.1(4) . . . . ?
N2 C1 C2 N5 -177.6(4) . . . . ?
N1 C1 C2 N5 4.5(7) . . . . ?
C4 N5 C2 C1 -67.5(6) . . . . ?
N6 N5 C2 C1 115.0(5) . . . . ?
C4 N5 C2 C3 114.5(5) . . . . ?
N6 N5 C2 C3 -63.0(6) . . . . ?
N2 N3 C3 C2 0.8(5) . . . . ?
K1 N3 C3 C2 165.9(3) 4_576 . . . ?
N2 N3 C3 N4 -178.3(3) . . . . ?
K1 N3 C3 N4 -13.2(5) 4_576 . . . ?
C1 C2 C3 N3 -1.0(5) . . . . ?
N5 C2 C3 N3 177.5(4) . . . . ?
C1 C2 C3 N4 178.0(4) . . . . ?
N5 C2 C3 N4 -3.5(7) . . . . ?
O5 N4 C3 N3 173.3(4) . . . . ?
O6 N4 C3 N3 -6.9(6) . . . . ?
O5 N4 C3 C2 -5.6(7) . . . . ?
O6 N4 C3 C2 174.2(4) . . . . ?
C5 N7 C4 N9 -178.6(4) . . . . ?
C5 N7 C4 N5 1.1(4) . . . . ?
K1 N9 C4 N7 -93.1(4) 2_655 . . . ?
K1 N9 C4 N5 87.2(4) 2_655 . . . ?
N6 N5 C4 N7 -1.5(4) . . . . ?
C2 N5 C4 N7 -179.2(4) . . . . ?
N6 N5 C4 N9 178.2(4) . . . . ?
C2 N5 C4 N9 0.4(7) . . . . ?
N5 N6 C5 N7 -0.6(4) . . . . ?
K1 N6 C5 N7 179.3(3) 2 . . . ?
N5 N6 C5 N8 -179.4(3) . . . . ?
K1 N6 C5 N8 0.5(5) 2 . . . ?
C4 N7 C5 N6 -0.3(5) . . . . ?
C4 N7 C5 N8 178.5(3) . . . . ?
O3 N8 C5 N6 -176.3(4) . . . . ?
O4 N8 C5 N6 4.4(5) . . . . ?
O3 N8 C5 N7 4.9(5) . . . . ?
O4 N8 C5 N7 -174.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.131
####################################################################### 
# 
# 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_exp_3247
_database_code_depnum_ccdc_archive 'CCDC 1449636'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;
_audit_creation_date             2015-05-27
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H2 N9 O4, C2 H7 N6'
_chemical_formula_sum            'C6 H9 N15 O4'
_chemical_formula_weight         355.28
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.2881(5)
_cell_length_b                   9.3424(8)
_cell_length_c                   11.2935(11)
_cell_angle_alpha                87.455(8)
_cell_angle_beta                 79.856(8)
_cell_angle_gamma                82.934(7)
_cell_volume                     647.94(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    102.1
_cell_measurement_theta_max      29.4235
_cell_measurement_theta_min      3.3072
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4442
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.31
_diffrn_ambient_temperature      102.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -13.2715   37.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5840   77.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5840   77.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega   62.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5840 -153.0000  139.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5840  -77.0000   90.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0161315000
_diffrn_orient_matrix_UB_12      0.0106413000
_diffrn_orient_matrix_UB_13      0.0594125000
_diffrn_orient_matrix_UB_21      -0.0714923000
_diffrn_orient_matrix_UB_22      -0.0518348000
_diffrn_orient_matrix_UB_23      0.0220706000
_diffrn_orient_matrix_UB_31      0.0891133000
_diffrn_orient_matrix_UB_32      -0.0551416000
_diffrn_orient_matrix_UB_33      -0.0072617000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2057
_reflns_number_total             2550
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1154
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N5 N 0.1845(3) 0.32498(18) 0.70314(17) 0.0176(4) Uani 1 1 d . . .
H5 H 0.2106 0.3854 0.6442 0.021 Uiso 1 1 calc R . .
O4 O 0.5239(2) 0.50871(15) 0.75301(14) 0.0205(4) Uani 1 1 d . . .
N1 N 0.5482(3) 0.19918(18) 0.69791(16) 0.0173(4) Uani 1 1 d . . .
H1 H 0.6031 0.1111 0.7065 0.021 Uiso 1 1 d R . .
O3 O 0.6765(2) 0.64994(15) 0.61205(15) 0.0225(4) Uani 1 1 d . . .
O1 O 0.8492(3) 0.02629(17) 0.34910(15) 0.0287(4) Uani 1 1 d . . .
O2 O 0.7259(2) -0.02962(16) 0.53470(15) 0.0249(4) Uani 1 1 d . . .
N8 N 0.7775(3) 0.05943(18) 0.45363(17) 0.0183(4) Uani 1 1 d . . .
N7 N 0.8294(3) 0.30673(18) 0.40427(16) 0.0168(4) Uani 1 1 d . . .
N2 N 0.2320(3) 0.15264(18) 0.83399(16) 0.0167(4) Uani 1 1 d . . .
C4 C 0.3308(3) 0.2263(2) 0.74240(19) 0.0149(5) Uani 1 1 d . . .
N6 N 0.7848(3) 0.43445(18) 0.45726(17) 0.0171(4) Uani 1 1 d . . .
N3 N 0.0188(3) 0.20840(18) 0.84862(17) 0.0197(4) Uani 1 1 d . . .
C2 C 0.6501(3) 0.2672(2) 0.5945(2) 0.0155(5) Uani 1 1 d . . .
N9 N 0.6234(3) 0.53097(18) 0.65005(17) 0.0175(4) Uani 1 1 d . . .
N4 N -0.0114(3) 0.31315(18) 0.77223(17) 0.0202(4) Uani 1 1 d . . .
C1 C 0.7521(3) 0.2078(2) 0.48573(19) 0.0144(5) Uani 1 1 d . . .
C3 C 0.6805(3) 0.4124(2) 0.57105(19) 0.0159(5) Uani 1 1 d . . .
N10 N 0.3101(3) 0.21637(17) 0.11878(16) 0.0156(4) Uani 1 1 d . . .
N15 N -0.0375(3) 0.35527(18) 0.14169(17) 0.0202(4) Uani 1 1 d . . .
H15A H -0.1231 0.4254 0.1180 0.024 Uiso 1 1 d R . .
H15B H -0.0738 0.3313 0.2162 0.024 Uiso 1 1 d R . .
N11 N 0.4784(3) 0.33337(17) -0.02720(16) 0.0180(4) Uani 1 1 d . . .
H11 H 0.5794 0.3591 -0.0828 0.022 Uiso 1 1 calc R . .
N12 N 0.2694(3) 0.40962(18) -0.00080(17) 0.0180(4) Uani 1 1 d . . .
N14 N 0.6748(3) 0.12159(18) 0.04032(17) 0.0212(4) Uani 1 1 d . . .
H14A H 0.7931 0.1364 -0.0073 0.025 Uiso 1 1 d R . .
H14B H 0.6706 0.0491 0.0900 0.025 Uiso 1 1 d R . .
N13 N 0.2706(3) 0.11565(18) 0.21356(17) 0.0202(4) Uani 1 1 d . . .
H13A H 0.2696 0.1594 0.2791 0.024 Uiso 1 1 d R . .
H13B H 0.1472 0.0868 0.2101 0.024 Uiso 1 1 d R . .
C5 C 0.1708(3) 0.3349(2) 0.0884(2) 0.0158(5) Uani 1 1 d . . .
C6 C 0.5022(3) 0.2177(2) 0.0431(2) 0.0166(5) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 H5 0.8600 . ?
N5 C4 1.338(2) . ?
N5 N4 1.351(2) . ?
O4 N9 1.241(2) . ?
N1 H1 0.8603 . ?
N1 C4 1.367(3) . ?
N1 C2 1.397(3) . ?
O3 N9 1.237(2) . ?
O1 N8 1.226(2) . ?
O2 N8 1.237(2) . ?
N8 C1 1.431(3) . ?
N7 N6 1.335(2) . ?
N7 C1 1.347(3) . ?
N2 C4 1.321(3) . ?
N2 N3 1.361(2) . ?
N6 C3 1.355(3) . ?
N3 N4 1.294(2) . ?
C2 C1 1.387(3) . ?
C2 C3 1.400(3) . ?
N9 C3 1.424(3) . ?
N10 N13 1.403(2) . ?
N10 C5 1.395(2) . ?
N10 C6 1.352(3) . ?
N15 H15A 0.8597 . ?
N15 H15B 0.8598 . ?
N15 C5 1.336(3) . ?
N11 H11 0.8600 . ?
N11 N12 1.405(2) . ?
N11 C6 1.321(2) . ?
N12 C5 1.308(3) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8596 . ?
N14 C6 1.318(3) . ?
N13 H13A 0.8604 . ?
N13 H13B 0.8599 . ?

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
C4 N5 H5 125.9 . . ?
C4 N5 N4 108.11(17) . . ?
N4 N5 H5 125.9 . . ?
C4 N1 H1 114.8 . . ?
C4 N1 C2 123.34(16) . . ?
C2 N1 H1 112.9 . . ?
O1 N8 O2 123.29(18) . . ?
O1 N8 C1 119.42(18) . . ?
O2 N8 C1 117.30(18) . . ?
N6 N7 C1 107.07(18) . . ?
C4 N2 N3 105.32(15) . . ?
N5 C4 N1 128.0(2) . . ?
N2 C4 N5 109.06(18) . . ?
N2 C4 N1 122.95(17) . . ?
N7 N6 C3 107.63(16) . . ?
N4 N3 N2 111.08(18) . . ?
N1 C2 C3 130.5(2) . . ?
C1 C2 N1 129.15(18) . . ?
C1 C2 C3 100.39(19) . . ?
O4 N9 C3 118.11(17) . . ?
O3 N9 O4 123.89(18) . . ?
O3 N9 C3 118.00(19) . . ?
N3 N4 N5 106.41(16) . . ?
N7 C1 N8 119.51(19) . . ?
N7 C1 C2 113.06(18) . . ?
C2 C1 N8 127.42(19) . . ?
N6 C3 C2 111.81(19) . . ?
N6 C3 N9 119.30(18) . . ?
C2 C3 N9 128.9(2) . . ?
C5 N10 N13 128.07(18) . . ?
C6 N10 N13 124.20(15) . . ?
C6 N10 C5 107.64(17) . . ?
H15A N15 H15B 113.5 . . ?
C5 N15 H15A 119.8 . . ?
C5 N15 H15B 120.1 . . ?
N12 N11 H11 123.8 . . ?
C6 N11 H11 123.8 . . ?
C6 N11 N12 112.39(18) . . ?
C5 N12 N11 103.65(15) . . ?
H14A N14 H14B 121.1 . . ?
C6 N14 H14A 119.1 . . ?
C6 N14 H14B 119.7 . . ?
N10 N13 H13A 107.0 . . ?
N10 N13 H13B 106.7 . . ?
H13A N13 H13B 112.6 . . ?
N15 C5 N10 121.25(19) . . ?
N12 C5 N10 110.59(18) . . ?
N12 C5 N15 127.98(17) . . ?
N11 C6 N10 105.71(17) . . ?
N14 C6 N10 126.43(19) . . ?
N14 C6 N11 127.9(2) . . ?

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
O4 N9 C3 N6 178.52(15) . . . . ?
O4 N9 C3 C2 -3.6(3) . . . . ?
N1 C2 C1 N8 -0.1(3) . . . . ?
N1 C2 C1 N7 178.73(16) . . . . ?
N1 C2 C3 N6 -178.74(17) . . . . ?
N1 C2 C3 N9 3.3(3) . . . . ?
O3 N9 C3 N6 -1.7(2) . . . . ?
O3 N9 C3 C2 176.13(17) . . . . ?
O1 N8 C1 N7 -7.4(3) . . . . ?
O1 N8 C1 C2 171.42(18) . . . . ?
O2 N8 C1 N7 172.27(15) . . . . ?
O2 N8 C1 C2 -9.0(3) . . . . ?
N7 N6 C3 C2 -1.3(2) . . . . ?
N7 N6 C3 N9 176.91(15) . . . . ?
N2 N3 N4 N5 1.6(2) . . . . ?
C4 N5 N4 N3 -1.1(2) . . . . ?
C4 N1 C2 C1 -115.9(2) . . . . ?
C4 N1 C2 C3 64.8(3) . . . . ?
C4 N2 N3 N4 -1.5(2) . . . . ?
N6 N7 C1 N8 -179.85(15) . . . . ?
N6 N7 C1 C2 1.2(2) . . . . ?
N3 N2 C4 N5 0.8(2) . . . . ?
N3 N2 C4 N1 -178.31(17) . . . . ?
C2 N1 C4 N5 -5.0(3) . . . . ?
C2 N1 C4 N2 173.87(18) . . . . ?
N4 N5 C4 N1 179.21(19) . . . . ?
N4 N5 C4 N2 0.2(2) . . . . ?
C1 N7 N6 C3 0.05(18) . . . . ?
C1 C2 C3 N6 1.9(2) . . . . ?
C1 C2 C3 N9 -176.11(17) . . . . ?
C3 C2 C1 N8 179.31(17) . . . . ?
C3 C2 C1 N7 -1.9(2) . . . . ?
N11 N12 C5 N10 0.4(2) . . . . ?
N11 N12 C5 N15 -174.70(19) . . . . ?
N12 N11 C6 N10 -0.9(2) . . . . ?
N12 N11 C6 N14 178.30(19) . . . . ?
N13 N10 C5 N15 -8.7(3) . . . . ?
N13 N10 C5 N12 175.81(17) . . . . ?
N13 N10 C6 N11 -175.82(16) . . . . ?
N13 N10 C6 N14 4.9(3) . . . . ?
C5 N10 C6 N11 1.1(2) . . . . ?
C5 N10 C6 N14 -178.11(19) . . . . ?
C6 N10 C5 N15 174.50(18) . . . . ?
C6 N10 C5 N12 -1.0(2) . . . . ?
C6 N11 N12 C5 0.3(2) . . . . ?

####################################################################### 
# 
# 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_bl85
_database_code_depnum_ccdc_archive 'CCDC 1449634'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 N9 O5'
_chemical_formula_weight         259.17

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.7451(9)
_cell_length_b                   7.1473(14)
_cell_length_c                   27.902(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.22(3)
_cell_angle_gamma                90.00
_cell_volume                     946.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      1.4597
_cell_measurement_theta_max      27.4662

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8552
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6342
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2134
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.1102P)²+1.1225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2134
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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
O1 O 0.4110(6) 0.3181(4) 0.32335(10) 0.0386(7) Uani 1 1 d . . .
O2 O 0.6162(6) 0.5299(4) 0.25078(9) 0.0391(7) Uani 1 1 d . . .
N3 N 0.8624(6) 1.0104(4) 0.33264(10) 0.0288(7) Uani 1 1 d . . .
H3A H 0.9316 0.9994 0.3032 0.035 Uiso 1 1 d R . .
H3B H 0.8024 1.1203 0.3436 0.035 Uiso 1 1 d R . .
N4 N 0.4890(6) 0.8824(4) 0.38038(10) 0.0277(7) Uani 1 1 d . . .
O5 O 0.0329(6) 0.4198(4) 0.35921(10) 0.0425(7) Uani 1 1 d . . .
C6 C 0.6720(7) 0.8772(5) 0.34206(11) 0.0259(7) Uani 1 1 d . . .
O7 O 0.9550(6) 0.7299(4) 0.26297(10) 0.0417(7) Uani 1 1 d . . .
N8 N 0.3212(6) 0.7256(4) 0.38326(10) 0.0288(7) Uani 1 1 d . . .
N9 N 0.2674(7) 1.0212(4) 0.44882(11) 0.0337(7) Uani 1 1 d . . .
N10 N 0.3265(7) 1.1840(4) 0.47058(11) 0.0342(7) Uani 1 1 d . . .
H10 H 0.2481 1.2310 0.4969 0.041 Uiso 1 1 d R . .
N11 N 0.2692(6) 0.4406(4) 0.34187(10) 0.0280(6) Uani 1 1 d . . .
N12 N 0.7320(6) 0.6514(4) 0.27471(10) 0.0303(7) Uani 1 1 d . . .
C13 C 0.4615(7) 1.0233(5) 0.41480(11) 0.0265(7) Uani 1 1 d . . .
N14 N 0.6289(7) 1.1746(5) 0.41525(11) 0.0377(8) Uani 1 1 d . . .
O15 O -0.1273(7) 0.6449(5) 0.45367(11) 0.0580(10) Uani 1 1 d . . .
H15A H -0.0155 0.6645 0.4310 0.070 Uiso 1 1 d R . .
H15B H -0.1820 0.5342 0.4496 0.070 Uiso 1 1 d R . .
N16 N 0.5345(7) 1.2767(5) 0.45164(11) 0.0395(8) Uani 1 1 d . . .
C17 C 0.6109(7) 0.7091(5) 0.31872(12) 0.0269(7) Uani 1 1 d . . .
C18 C 0.3951(7) 0.6254(5) 0.34608(12) 0.0265(7) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N11 1.220(4) . ?
O2 N12 1.224(4) . ?
N3 C6 1.339(4) . ?
N3 H3A 0.8901 . ?
N3 H3B 0.8901 . ?
N4 N8 1.377(4) . ?
N4 C6 1.381(4) . ?
N4 C13 1.398(4) . ?
O5 N11 1.232(4) . ?
C6 C17 1.397(5) . ?
O7 N12 1.243(4) . ?
N8 C18 1.309(4) . ?
N9 C13 1.325(4) . ?
N9 N10 1.342(4) . ?
N10 N16 1.302(5) . ?
N10 H10 0.8900 . ?
N11 C18 1.454(4) . ?
N12 C17 1.419(4) . ?
C13 N14 1.342(4) . ?
N14 N16 1.330(4) . ?
O15 H15A 0.8400 . ?
O15 H15B 0.8399 . ?
C17 C18 1.413(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
C6 N3 H3A 111.7 . . ?
C6 N3 H3B 110.1 . . ?
H3A N3 H3B 121.0 . . ?
N8 N4 C6 112.9(3) . . ?
N8 N4 C13 119.4(3) . . ?
C6 N4 C13 127.7(3) . . ?
N3 C6 N4 124.0(3) . . ?
N3 C6 C17 131.2(3) . . ?
N4 C6 C17 104.7(3) . . ?
C18 N8 N4 104.0(3) . . ?
C13 N9 N10 99.8(3) . . ?
N16 N10 N9 114.5(3) . . ?
N16 N10 H10 117.6 . . ?
N9 N10 H10 127.8 . . ?
O1 N11 O5 125.7(3) . . ?
O1 N11 C18 117.4(3) . . ?
O5 N11 C18 116.8(3) . . ?
O2 N12 O7 123.9(3) . . ?
O2 N12 C17 119.7(3) . . ?
O7 N12 C17 116.4(3) . . ?
N9 C13 N14 114.5(3) . . ?
N9 C13 N4 123.5(3) . . ?
N14 C13 N4 122.0(3) . . ?
N16 N14 C13 104.4(3) . . ?
H15A O15 H15B 104.5 . . ?
N10 N16 N14 106.8(3) . . ?
C6 C17 C18 105.2(3) . . ?
C6 C17 N12 124.7(3) . . ?
C18 C17 N12 129.9(3) . . ?
N8 C18 C17 113.2(3) . . ?
N8 C18 N11 116.7(3) . . ?
C17 C18 N11 129.7(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
N8 N4 C6 N3 -177.7(3) . . . . ?
C13 N4 C6 N3 1.7(5) . . . . ?
N8 N4 C6 C17 1.5(4) . . . . ?
C13 N4 C6 C17 -179.1(3) . . . . ?
C6 N4 N8 C18 -1.5(4) . . . . ?
C13 N4 N8 C18 179.0(3) . . . . ?
C13 N9 N10 N16 0.3(4) . . . . ?
N10 N9 C13 N14 0.1(4) . . . . ?
N10 N9 C13 N4 -178.6(3) . . . . ?
N8 N4 C13 N9 -4.8(5) . . . . ?
C6 N4 C13 N9 175.8(3) . . . . ?
N8 N4 C13 N14 176.6(3) . . . . ?
C6 N4 C13 N14 -2.9(5) . . . . ?
N9 C13 N14 N16 -0.5(4) . . . . ?
N4 C13 N14 N16 178.3(3) . . . . ?
N9 N10 N16 N14 -0.6(4) . . . . ?
C13 N14 N16 N10 0.7(4) . . . . ?
N3 C6 C17 C18 178.3(3) . . . . ?
N4 C6 C17 C18 -0.8(4) . . . . ?
N3 C6 C17 N12 -6.4(6) . . . . ?
N4 C6 C17 N12 174.5(3) . . . . ?
O2 N12 C17 C6 -160.8(3) . . . . ?
O7 N12 C17 C6 19.4(5) . . . . ?
O2 N12 C17 C18 13.3(5) . . . . ?
O7 N12 C17 C18 -166.5(3) . . . . ?
N4 N8 C18 C17 0.9(4) . . . . ?
N4 N8 C18 N11 174.6(3) . . . . ?
C6 C17 C18 N8 0.0(4) . . . . ?
N12 C17 C18 N8 -175.0(3) . . . . ?
C6 C17 C18 N11 -172.7(3) . . . . ?
N12 C17 C18 N11 12.3(6) . . . . ?
O1 N11 C18 N8 -147.8(3) . . . . ?
O5 N11 C18 N8 29.2(4) . . . . ?
O1 N11 C18 C17 24.7(5) . . . . ?
O5 N11 C18 C17 -158.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_bl80
_database_code_depnum_ccdc_archive 'CCDC 1449633'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H10 N10 O6'
_chemical_formula_weight         294.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   10.035(2)
_cell_length_b                   6.9626(14)
_cell_length_c                   16.699(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.60(3)
_cell_angle_gamma                90.00
_cell_volume                     1166.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3752
_cell_measurement_theta_min      2.0304
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7877
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2627
_reflns_number_gt                2338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0620P)²+0.5110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_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
O1 O 0.17619(15) 0.2005(2) 0.78150(9) 0.0259(3) Uani 1 1 d . . .
O2 O 0.04506(16) 0.4473(2) 0.78036(9) 0.0321(4) Uani 1 1 d . . .
O3 O 0.37547(14) 0.2538(2) 0.67401(9) 0.0274(4) Uani 1 1 d . . .
O4 O 0.37158(14) 0.1306(2) 0.55365(9) 0.0284(4) Uani 1 1 d . . .
N1 N 0.10472(16) 0.3184(2) 0.74726(10) 0.0179(3) Uani 1 1 d . . .
N2 N 0.31482(16) 0.2021(2) 0.61235(10) 0.0197(4) Uani 1 1 d . . .
N3 N 0.13577(16) 0.1598(2) 0.45980(10) 0.0196(4) Uani 1 1 d . . .
H3A H 0.0790 0.1879 0.4196 0.024 Uiso 1 1 d R . .
H3B H 0.2204 0.1228 0.4568 0.024 Uiso 1 1 d R . .
N4 N -0.03271(15) 0.3308(2) 0.63042(9) 0.0160(3) Uani 1 1 d . . .
N5 N -0.02209(15) 0.2823(2) 0.55050(9) 0.0153(3) Uani 1 1 d . . .
N6 N -0.24808(15) 0.3787(2) 0.51686(10) 0.0192(4) Uani 1 1 d . . .
N7 N -0.31998(16) 0.3694(3) 0.44691(10) 0.0215(4) Uani 1 1 d . . .
N8 N -0.24797(17) 0.2934(3) 0.39125(10) 0.0227(4) Uani 1 1 d . . .
N9 N -0.12594(17) 0.2484(2) 0.42127(10) 0.0207(4) Uani 1 1 d . . .
C13 C -0.13182(18) 0.3028(3) 0.49735(11) 0.0154(4) Uani 1 1 d . . .
C17 C 0.08622(18) 0.2991(3) 0.66083(11) 0.0152(4) Uani 1 1 d . . .
C19 C 0.10298(18) 0.2167(3) 0.53207(11) 0.0151(4) Uani 1 1 d . . .
C20 C 0.17701(18) 0.2278(3) 0.60479(11) 0.0161(4) Uani 1 1 d . . .
O5 O 0.37330(14) 0.0263(2) 0.37808(9) 0.0248(3) Uani 1 1 d . . .
H5A H 0.3462 -0.0564 0.3448 0.030 Uiso 1 1 d R . .
H5B H 0.4355 -0.0347 0.4012 0.030 Uiso 1 1 d R . .
O6 O 0.71097(14) 0.2675(2) 0.72400(9) 0.0250(3) Uani 1 1 d . . .
H6A H 0.7199 0.2551 0.7739 0.030 Uiso 1 1 d R . .
H6B H 0.7832 0.3131 0.7083 0.030 Uiso 1 1 d R . .
N10 N 0.41538(16) 0.0729(3) 0.86902(10) 0.0216(4) Uani 1 1 d . . .
H10A H 0.3954 0.1952 0.8589 0.026 Uiso 1 1 d R . .
H10B H 0.4172 -0.0107 0.8287 0.026 Uiso 1 1 d R . .
H10C H 0.3584 0.0033 0.8968 0.026 Uiso 1 1 d R . .
H10D H 0.4941 0.0513 0.8932 0.026 Uiso 1 1 d 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
O1 N1 1.222(2) . ?
O2 N1 1.220(2) . ?
O3 N2 1.235(2) . ?
O4 N2 1.251(2) . ?
N1 C17 1.456(2) . ?
N2 C20 1.397(2) . ?
N3 C19 1.321(2) . ?
N3 H3A 0.8899 . ?
N3 H3B 0.8900 . ?
N4 C17 1.303(2) . ?
N4 N5 1.384(2) . ?
N5 C19 1.378(2) . ?
N5 C13 1.402(2) . ?
N6 C13 1.329(2) . ?
N6 N7 1.357(2) . ?
N7 N8 1.305(2) . ?
N8 N9 1.347(2) . ?
N9 C13 1.329(2) . ?
C17 C20 1.414(3) . ?
C19 C20 1.408(3) . ?
O5 H5A 0.8402 . ?
O5 H5B 0.8401 . ?
O6 H6A 0.8400 . ?
O6 H6B 0.8399 . ?
N10 H10A 0.8900 . ?
N10 H10B 0.8901 . ?
N10 H10C 0.8900 . ?
N10 H10D 0.8899 . ?

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 N1 O1 124.87(17) . . ?
O2 N1 C17 117.79(16) . . ?
O1 N1 C17 117.31(16) . . ?
O3 N2 O4 123.02(16) . . ?
O3 N2 C20 120.11(17) . . ?
O4 N2 C20 116.84(16) . . ?
C19 N3 H3A 116.9 . . ?
C19 N3 H3B 113.6 . . ?
H3A N3 H3B 127.8 . . ?
C17 N4 N5 103.90(15) . . ?
C19 N5 N4 113.04(15) . . ?
C19 N5 C13 126.61(16) . . ?
N4 N5 C13 120.35(15) . . ?
C13 N6 N7 102.66(16) . . ?
N8 N7 N6 109.91(15) . . ?
N7 N8 N9 110.17(16) . . ?
C13 N9 N8 103.03(16) . . ?
N9 C13 N6 114.23(17) . . ?
N9 C13 N5 121.40(17) . . ?
N6 C13 N5 124.36(17) . . ?
N4 C17 C20 113.68(16) . . ?
N4 C17 N1 117.44(16) . . ?
C20 C17 N1 128.43(16) . . ?
N3 C19 N5 123.72(17) . . ?
N3 C19 C20 131.75(17) . . ?
N5 C19 C20 104.54(16) . . ?
N2 C20 C19 124.62(17) . . ?
N2 C20 C17 129.77(17) . . ?
C19 C20 C17 104.82(16) . . ?
H5A O5 H5B 100.3 . . ?
H6A O6 H6B 106.2 . . ?
H10A N10 H10B 119.4 . . ?
H10A N10 H10C 118.4 . . ?
H10B N10 H10C 93.7 . . ?
H10A N10 H10D 116.1 . . ?
H10B N10 H10D 101.3 . . ?
H10C N10 H10D 104.3 . . ?

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
C17 N4 N5 C19 1.3(2) . . . . ?
C17 N4 N5 C13 -178.38(16) . . . . ?
C13 N6 N7 N8 -0.2(2) . . . . ?
N6 N7 N8 N9 0.1(2) . . . . ?
N7 N8 N9 C13 0.0(2) . . . . ?
N8 N9 C13 N6 -0.2(2) . . . . ?
N8 N9 C13 N5 -179.32(17) . . . . ?
N7 N6 C13 N9 0.2(2) . . . . ?
N7 N6 C13 N5 179.37(17) . . . . ?
C19 N5 C13 N9 3.7(3) . . . . ?
N4 N5 C13 N9 -176.67(17) . . . . ?
C19 N5 C13 N6 -175.36(19) . . . . ?
N4 N5 C13 N6 4.3(3) . . . . ?
N5 N4 C17 C20 -1.0(2) . . . . ?
N5 N4 C17 N1 -173.89(15) . . . . ?
O2 N1 C17 N4 -38.0(3) . . . . ?
O1 N1 C17 N4 140.02(18) . . . . ?
O2 N1 C17 C20 150.3(2) . . . . ?
O1 N1 C17 C20 -31.7(3) . . . . ?
N4 N5 C19 N3 179.09(17) . . . . ?
C13 N5 C19 N3 -1.3(3) . . . . ?
N4 N5 C19 C20 -1.1(2) . . . . ?
C13 N5 C19 C20 178.54(17) . . . . ?
O3 N2 C20 C19 164.51(18) . . . . ?
O4 N2 C20 C19 -13.6(3) . . . . ?
O3 N2 C20 C17 -3.8(3) . . . . ?
O4 N2 C20 C17 178.08(19) . . . . ?
N3 C19 C20 N2 9.5(3) . . . . ?
N5 C19 C20 N2 -170.26(17) . . . . ?
N3 C19 C20 C17 -179.7(2) . . . . ?
N5 C19 C20 C17 0.5(2) . . . . ?
N4 C17 C20 N2 170.39(19) . . . . ?
N1 C17 C20 N2 -17.6(3) . . . . ?
N4 C17 C20 C19 0.3(2) . . . . ?
N1 C17 C20 C19 172.31(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.110
####################################################################### 
# 
# 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_bl90a
_audit_block_doi                 10.5517/ccdc.csd.cc1kngf3
_database_code_depnum_ccdc_archive 'CCDC 1449635'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/asia.201600967 2016
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Br F3 N2 O4'
_chemical_formula_sum            'C19 H16 Br F3 N2 O4'
_chemical_formula_weight         473.25
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.3074(19)
_cell_length_b                   10.844(2)
_cell_length_c                   18.529(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1870.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6478
_cell_measurement_theta_min      2.1983
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22087
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4193
_reflns_number_gt                4120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0708P)²+0.6288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   0.023(9)
_refine_ls_number_reflns         4193
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.91071(4) 0.36629(4) 0.52874(2) 0.03618(14) Uani 1 1 d . . .
F1 F 0.8993(3) 0.67300(18) 0.86707(13) 0.0295(5) Uani 1 1 d . . .
F2 F 1.0252(2) 0.5072(2) 0.86328(12) 0.0264(5) Uani 1 1 d . . .
F3 F 0.8481(3) 0.5216(2) 0.93710(11) 0.0273(5) Uani 1 1 d . . .
N2 N 0.9266(3) 0.3268(2) 0.75731(16) 0.0183(5) Uani 1 1 d . . .
H2 H 1.0052 0.3394 0.7837 0.022 Uiso 1 1 d R . .
O4 O 0.7255(3) 0.2891(2) 0.92243(15) 0.0256(5) Uani 1 1 d . . .
N1 N 0.7452(3) 0.5994(3) 0.68904(16) 0.0215(6) Uani 1 1 d . . .
O2 O 0.6518(3) 0.5354(3) 0.66209(16) 0.0296(6) Uani 1 1 d . . .
C7 C 0.9135(4) 0.4197(3) 0.70032(17) 0.0182(6) Uani 1 1 d . . .
H7 H 0.8399 0.3905 0.6649 0.022 Uiso 1 1 calc R . .
C11 C 0.8891(4) 0.5506(3) 0.87006(18) 0.0202(6) Uani 1 1 d . . .
C5 C 1.1734(4) 0.4818(3) 0.6973(2) 0.0251(7) Uani 1 1 d . . .
H5 H 1.1655 0.4985 0.7475 0.030 Uiso 1 1 calc R . .
O3 O 0.9562(3) 0.2459(3) 0.89559(15) 0.0295(6) Uani 1 1 d . . .
C10 C 0.8092(4) 0.3508(3) 0.80769(18) 0.0189(6) Uani 1 1 d . . .
H10 H 0.7192 0.3142 0.7874 0.023 Uiso 1 1 calc R . .
C1 C 1.0684(4) 0.4188(3) 0.58641(19) 0.0233(7) Uani 1 1 d . . .
C18 C 0.4655(4) 0.7112(3) 0.8370(2) 0.0243(7) Uani 1 1 d . . .
H18 H 0.4469 0.7973 0.8357 0.029 Uiso 1 1 calc R . .
C17 C 0.3545(4) 0.6299(4) 0.85105(19) 0.0239(7) Uani 1 1 d . . .
H17 H 0.2597 0.6596 0.8589 0.029 Uiso 1 1 calc R . .
O1 O 0.7548(3) 0.7126(2) 0.68048(16) 0.0304(6) Uani 1 1 d . . .
C3 C 1.3184(4) 0.4743(4) 0.5907(2) 0.0297(8) Uani 1 1 d . . .
H3 H 1.4083 0.4853 0.5673 0.036 Uiso 1 1 calc R . .
C15 C 0.5219(4) 0.4593(3) 0.84086(18) 0.0205(7) Uani 1 1 d . . .
H15 H 0.5402 0.3731 0.8421 0.025 Uiso 1 1 calc R . .
C8 C 0.8551(4) 0.5386(3) 0.73744(18) 0.0179(6) Uani 1 1 d . . .
H8 H 0.9364 0.5970 0.7463 0.021 Uiso 1 1 calc R . .
C16 C 0.3834(4) 0.5038(3) 0.8535(2) 0.0226(7) Uani 1 1 d . . .
H16 H 0.3079 0.4475 0.8638 0.027 Uiso 1 1 calc R . .
C6 C 1.0528(4) 0.4405(3) 0.66011(18) 0.0185(6) Uani 1 1 d . . .
C19 C 0.6045(4) 0.6680(3) 0.82489(19) 0.0212(6) Uani 1 1 d . . .
H19 H 0.6797 0.7250 0.8155 0.025 Uiso 1 1 calc R . .
C9 C 0.7894(4) 0.4965(3) 0.81219(18) 0.0180(6) Uani 1 1 d . . .
C14 C 0.6344(4) 0.5423(3) 0.82638(18) 0.0187(6) Uani 1 1 d . . .
C2 C 1.2010(4) 0.4328(4) 0.5516(2) 0.0282(8) Uani 1 1 d . . .
H2A H 1.2104 0.4141 0.5018 0.034 Uiso 1 1 calc R . .
C12 C 0.8410(4) 0.2887(3) 0.8796(2) 0.0209(7) Uani 1 1 d . . .
C13 C 0.7499(5) 0.2554(4) 0.9974(2) 0.0319(9) Uani 1 1 d . . .
H13A H 0.7879 0.1712 0.9997 0.048 Uiso 1 1 calc R . .
H13B H 0.6590 0.2596 1.0240 0.048 Uiso 1 1 calc R . .
H13C H 0.8192 0.3125 1.0190 0.048 Uiso 1 1 calc R . .
C4 C 1.3053(4) 0.4996(4) 0.6634(2) 0.0281(8) Uani 1 1 d . . .
H4 H 1.3855 0.5288 0.6900 0.034 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
Br1 C1 1.903(4) . ?
F1 C11 1.332(4) . ?
F2 C11 1.357(4) . ?
F3 C11 1.337(4) . ?
N2 C10 1.461(4) . ?
N2 C7 1.464(4) . ?
N2 H2 0.8899 . ?
O4 C12 1.336(4) . ?
O4 C13 1.454(5) . ?
N1 O2 1.220(4) . ?
N1 O1 1.241(4) . ?
N1 C8 1.512(4) . ?
C7 C6 1.512(5) . ?
C7 C8 1.559(4) . ?
C7 H7 1.0000 . ?
C11 C9 1.535(5) . ?
C5 C6 1.391(5) . ?
C5 C4 1.392(5) . ?
C5 H5 0.9500 . ?
O3 C12 1.205(5) . ?
C10 C12 1.522(5) . ?
C10 C9 1.594(4) . ?
C10 H10 1.0000 . ?
C1 C6 1.393(5) . ?
C1 C2 1.400(5) . ?
C18 C17 1.383(5) . ?
C18 C19 1.394(5) . ?
C18 H18 0.9500 . ?
C17 C16 1.395(5) . ?
C17 H17 0.9500 . ?
C3 C4 1.380(6) . ?
C3 C2 1.385(6) . ?
C3 H3 0.9500 . ?
C15 C16 1.397(5) . ?
C15 C14 1.407(5) . ?
C15 H15 0.9500 . ?
C8 C9 1.581(5) . ?
C8 H8 1.0000 . ?
C16 H16 0.9500 . ?
C19 C14 1.391(5) . ?
C19 H19 0.9500 . ?
C9 C14 1.548(5) . ?
C2 H2A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C7 106.0(3) . . ?
C10 N2 H2 103.7 . . ?
C7 N2 H2 111.0 . . ?
C12 O4 C13 116.1(3) . . ?
O2 N1 O1 124.2(3) . . ?
O2 N1 C8 118.5(3) . . ?
O1 N1 C8 117.3(3) . . ?
N2 C7 C6 112.8(3) . . ?
N2 C7 C8 106.2(3) . . ?
C6 C7 C8 113.1(3) . . ?
N2 C7 H7 108.2 . . ?
C6 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
F1 C11 F3 107.1(3) . . ?
F1 C11 F2 106.0(3) . . ?
F3 C11 F2 105.7(3) . . ?
F1 C11 C9 113.2(3) . . ?
F3 C11 C9 112.7(3) . . ?
F2 C11 C9 111.6(3) . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C10 C12 109.6(3) . . ?
N2 C10 C9 107.2(3) . . ?
C12 C10 C9 114.5(3) . . ?
N2 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
C6 C1 C2 121.7(3) . . ?
C6 C1 Br1 121.3(3) . . ?
C2 C1 Br1 117.0(3) . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N1 C8 C7 109.6(3) . . ?
N1 C8 C9 112.5(3) . . ?
C7 C8 C9 106.4(2) . . ?
N1 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 C7 119.7(3) . . ?
C1 C6 C7 123.2(3) . . ?
C14 C19 C18 120.8(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C11 C9 C14 108.8(3) . . ?
C11 C9 C8 105.5(3) . . ?
C14 C9 C8 114.6(3) . . ?
C11 C9 C10 110.2(3) . . ?
C14 C9 C10 115.8(3) . . ?
C8 C9 C10 101.3(2) . . ?
C19 C14 C15 118.8(3) . . ?
C19 C14 C9 119.8(3) . . ?
C15 C14 C9 121.4(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
O3 C12 O4 124.9(3) . . ?
O3 C12 C10 123.9(3) . . ?
O4 C12 C10 111.2(3) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?

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
C10 N2 C7 C6 158.2(3) . . . . ?
C10 N2 C7 C8 33.8(3) . . . . ?
C7 N2 C10 C12 -161.6(3) . . . . ?
C7 N2 C10 C9 -36.7(3) . . . . ?
C19 C18 C17 C16 0.5(6) . . . . ?
O2 N1 C8 C7 47.2(4) . . . . ?
O1 N1 C8 C7 -134.1(3) . . . . ?
O2 N1 C8 C9 -71.0(4) . . . . ?
O1 N1 C8 C9 107.7(3) . . . . ?
N2 C7 C8 N1 -139.8(3) . . . . ?
C6 C7 C8 N1 96.0(3) . . . . ?
N2 C7 C8 C9 -17.8(3) . . . . ?
C6 C7 C8 C9 -142.0(3) . . . . ?
C18 C17 C16 C15 -1.0(6) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C2 C1 C6 C5 2.6(5) . . . . ?
Br1 C1 C6 C5 -178.3(3) . . . . ?
C2 C1 C6 C7 -176.5(3) . . . . ?
Br1 C1 C6 C7 2.5(4) . . . . ?
N2 C7 C6 C5 -60.5(4) . . . . ?
C8 C7 C6 C5 60.1(4) . . . . ?
N2 C7 C6 C1 118.7(3) . . . . ?
C8 C7 C6 C1 -120.8(3) . . . . ?
C17 C18 C19 C14 0.2(6) . . . . ?
F1 C11 C9 C14 -64.5(4) . . . . ?
F3 C11 C9 C14 57.2(4) . . . . ?
F2 C11 C9 C14 176.0(3) . . . . ?
F1 C11 C9 C8 58.9(4) . . . . ?
F3 C11 C9 C8 -179.3(3) . . . . ?
F2 C11 C9 C8 -60.5(3) . . . . ?
F1 C11 C9 C10 167.5(3) . . . . ?
F3 C11 C9 C10 -70.8(3) . . . . ?
F2 C11 C9 C10 48.0(4) . . . . ?
N1 C8 C9 C11 -128.6(3) . . . . ?
C7 C8 C9 C11 111.4(3) . . . . ?
N1 C8 C9 C14 -8.8(4) . . . . ?
C7 C8 C9 C14 -128.9(3) . . . . ?
N1 C8 C9 C10 116.5(3) . . . . ?
C7 C8 C9 C10 -3.5(3) . . . . ?
N2 C10 C9 C11 -87.4(3) . . . . ?
C12 C10 C9 C11 34.4(4) . . . . ?
N2 C10 C9 C14 148.6(3) . . . . ?
C12 C10 C9 C14 -89.6(4) . . . . ?
N2 C10 C9 C8 24.0(3) . . . . ?
C12 C10 C9 C8 145.8(3) . . . . ?
C18 C19 C14 C15 -0.4(5) . . . . ?
C18 C19 C14 C9 179.6(3) . . . . ?
C16 C15 C14 C19 0.0(5) . . . . ?
C16 C15 C14 C9 180.0(3) . . . . ?
C11 C9 C14 C19 60.9(4) . . . . ?
C8 C9 C14 C19 -57.0(4) . . . . ?
C10 C9 C14 C19 -174.4(3) . . . . ?
C11 C9 C14 C15 -119.1(3) . . . . ?
C8 C9 C14 C15 123.0(3) . . . . ?
C10 C9 C14 C15 5.6(5) . . . . ?
C4 C3 C2 C1 1.1(6) . . . . ?
C6 C1 C2 C3 -2.8(6) . . . . ?
Br1 C1 C2 C3 178.2(3) . . . . ?
C13 O4 C12 O3 11.5(5) . . . . ?
C13 O4 C12 C10 -168.0(3) . . . . ?
N2 C10 C12 O3 12.0(5) . . . . ?
C9 C10 C12 O3 -108.6(4) . . . . ?
N2 C10 C12 O4 -168.5(3) . . . . ?
C9 C10 C12 O4 70.9(4) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C6 C5 C4 C3 -0.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.150
