# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_TABQ3
_database_code_depnum_ccdc_archive 'CCDC 1409346'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C6 H8 N4 O2'
_chemical_formula_moiety         'C6 H8 N4 O2'
_chemical_formula_weight         168.15
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_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
#------------------------------------------------------------------------------
_cell_length_a                   3.61996(17)
_cell_length_b                   12.9546(5)
_cell_length_c                   7.0224(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.632(3)
_cell_angle_gamma                90.0000
_cell_volume                     328.24(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1278
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      68.06
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             176.00
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.945

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            5427
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         6.836
_diffrn_reflns_theta_full        68.200
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             596
_reflns_number_gt                504
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1354
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         596
_refine_ls_number_parameters     71
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0770P)²+0.1786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3960(4) 0.08400(10) 0.7962(2) 0.0216(5) Uani 1 4 d . . .
N1 N 0.2498(5) 0.20945(13) 0.4916(3) 0.0215(6) Uani 1 4 d . . .
N2 N 0.1579(5) -0.11067(15) 0.8360(3) 0.0224(5) Uani 1 4 d . . .
C1 C 0.1309(6) 0.10532(15) 0.4839(3) 0.0186(6) Uani 1 4 d . . .
C2 C 0.2111(6) 0.04676(15) 0.6570(3) 0.0192(6) Uani 1 4 d . . .
C3 C 0.0683(5) -0.06217(15) 0.6683(3) 0.0191(6) Uani 1 4 d . . .
H1 H 0.266(8) -0.077(2) 0.925(4) 0.027(7) Uiso 1 4 d . . .
H2 H 0.030(8) -0.168(2) 0.874(4) 0.043(8) Uiso 1 4 d . . .
H3 H 0.479(8) 0.218(2) 0.567(4) 0.034(7) Uiso 1 4 d . . .
H4 H 0.248(7) 0.2342(19) 0.375(4) 0.024(6) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C2 1.237(2) yes . .
N1 C1 1.416(3) yes . .
N2 C3 1.351(3) yes . .
C1 C2 1.443(3) yes . .
C1 C3 1.360(3) yes . 3_556
C2 C3 1.507(3) yes . .
N1 H3 0.95(3) no . .
N1 H4 0.88(3) no . .
N2 H1 0.83(3) no . .
N2 H2 0.93(3) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N1 C1 C2 115.39(17) yes . . .
N1 C1 C3 124.20(18) yes . . 3_556
C2 C1 C3 120.27(18) yes . . 3_556
O1 C2 C1 121.34(18) yes . . .
O1 C2 C3 119.30(17) yes . . .
C1 C2 C3 119.36(17) yes . . .
N2 C3 C1 124.65(19) yes . . 3_556
N2 C3 C2 114.98(17) yes . . .
C1 C3 C2 120.37(18) yes 3_556 . .
C1 N1 H3 112.3(15) no . . .
C1 N1 H4 109.3(17) no . . .
H3 N1 H4 115(2) no . . .
C3 N2 H1 118.6(19) no . . .
C3 N2 H2 122.2(18) no . . .
H1 N2 H2 115(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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 O1 -5.2(3) no . . . .
N1 C1 C2 C3 175.04(15) no . . . .
N1 C1 C3 N2 4.5(3) no . . 3_556 3_556
N1 C1 C3 C2 -174.64(17) no . . 3_556 3_556
C2 C1 C3 N2 179.86(17) no . . 3_556 3_556
C2 C1 C3 C2 0.7(3) no . . 3_556 3_556
C3 C1 C2 O1 179.01(18) no 3_556 . . .
C3 C1 C2 C3 -0.7(3) no 3_556 . . .
O1 C2 C3 N2 0.2(3) no . . . .
O1 C2 C3 C1 -179.01(17) no . . . 3_556
C1 C2 C3 N2 179.94(16) no . . . .
C1 C2 C3 C1 0.7(3) no . . . 3_556

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.704(2) no . .
O1 N2 2.687(2) no . .
O1 C1 3.594(2) no . 3_556
O1 C3 3.558(2) no . 3_556
N1 N2 2.926(3) no . 3_556
C1 C1 2.903(3) no . 3_556
C2 C2 2.850(3) no . 3_556
C3 C3 2.871(3) no . 3_556
O1 N1 3.073(2) no . 4_555
O1 N2 3.413(2) no . 3_557
O1 N2 2.954(2) no . 3_657
O1 C1 3.593(3) no . 1_655
O1 C2 3.219(3) no . 1_655
O1 C3 3.266(2) no . 1_655
N1 O1 3.073(2) no . 4_554
N1 N2 3.060(3) no . 2_556
N1 N2 3.328(3) no . 2_656
N1 N2 3.511(3) no . 3_656
N1 C1 3.468(3) no . 1_655
N1 C3 3.383(3) no . 3_656
N2 O1 3.413(2) no . 3_557
N2 O1 2.954(2) no . 3_657
N2 N1 3.060(3) no . 2_546
N2 N1 3.328(3) no . 2_646
N2 N1 3.511(3) no . 3_656
N2 C1 3.551(3) no . 3_656
C1 O1 3.593(3) no . 1_455
C1 N1 3.468(3) no . 1_455
C1 N2 3.551(3) no . 3_656
C1 C2 3.304(3) no . 3_656
C1 C3 3.219(3) no . 3_656
C2 O1 3.219(3) no . 1_455
C2 C1 3.304(3) no . 3_656
C2 C2 3.384(3) no . 3_656
C2 C3 3.404(3) no . 1_655
C3 O1 3.266(2) no . 1_455
C3 N1 3.383(3) no . 3_656
C3 C1 3.219(3) no . 3_656
C3 C2 3.404(3) no . 1_455
O1 H1 2.34(3) no . .
O1 H2 3.59(3) no . .
O1 H3 2.40(3) no . .
O1 H4 3.55(3) no . .
N1 H2 2.73(3) no . 3_556
N2 H4 2.56(3) no . 3_556
C1 H1 3.13(3) no . 3_556
C1 H2 2.66(3) no . 3_556
C2 H1 2.47(3) no . .
C2 H2 3.27(3) no . .
C2 H3 2.52(3) no . .
C2 H4 3.14(3) no . .
C3 H3 3.19(3) no . 3_556
C3 H4 2.51(3) no . 3_556
H1 H4 3.38(4) no . 3_556
H2 H3 3.53(4) no . 3_556
H2 H4 2.12(4) no . 3_556
O1 H1 3.21(3) no . 3_557
O1 H1 2.22(3) no . 3_657
O1 H2 3.09(3) no . 3_557
O1 H2 3.18(3) no . 3_657
O1 H3 3.19(3) no . 4_555
O1 H4 2.49(3) no . 4_555
N1 H1 3.41(3) no . 2_556
N1 H1 3.30(3) no . 2_656
N1 H2 2.14(3) no . 2_556
N1 H2 3.13(3) no . 2_656
N1 H3 2.88(3) no . 1_455
N1 H3 3.30(3) no . 4_554
N1 H4 2.79(3) no . 4_555
N2 H1 3.37(3) no . 1_455
N2 H1 3.39(3) no . 3_557
N2 H1 3.54(3) no . 3_657
N2 H2 3.24(3) no . 1_655
N2 H3 3.31(3) no . 2_546
N2 H3 2.64(3) no . 2_646
N2 H3 3.50(3) no . 3_656
N2 H4 3.29(3) no . 2_546
N2 H4 3.48(3) no . 2_646
N2 H4 3.15(3) no . 3_656
C1 H2 3.17(3) no . 2_556
C1 H3 2.87(3) no . 1_455
C1 H4 3.44(3) no . 4_555
C2 H1 3.54(3) no . 3_557
C2 H1 3.38(3) no . 3_657
C2 H3 3.48(3) no . 1_455
C2 H4 3.22(3) no . 4_555
C3 H1 3.55(3) no . 1_455
C3 H3 3.15(3) no . 3_656
C3 H4 3.36(3) no . 3_656
H1 O1 3.21(3) no . 3_557
H1 O1 2.22(3) no . 3_657
H1 N1 3.41(3) no . 2_546
H1 N1 3.30(3) no . 2_646
H1 N2 3.37(3) no . 1_655
H1 N2 3.39(3) no . 3_557
H1 N2 3.54(3) no . 3_657
H1 C2 3.54(3) no . 3_557
H1 C2 3.38(3) no . 3_657
H1 C3 3.55(3) no . 1_655
H1 H1 3.02(4) no . 3_557
H1 H1 2.77(4) no . 3_657
H1 H2 3.06(4) no . 1_655
H1 H3 2.81(4) no . 2_646
H1 H4 3.44(4) no . 2_546
H1 H4 3.26(4) no . 2_646
H1 H4 3.50(4) no . 3_656
H2 O1 3.09(3) no . 3_557
H2 O1 3.18(3) no . 3_657
H2 N1 2.14(3) no . 2_546
H2 N1 3.13(3) no . 2_646
H2 N2 3.24(3) no . 1_455
H2 C1 3.17(3) no . 2_546
H2 H1 3.06(4) no . 1_455
H2 H3 2.42(4) no . 2_546
H2 H3 2.32(4) no . 2_646
H2 H4 2.45(4) no . 2_546
H2 H4 3.29(4) no . 2_646
H2 H4 3.37(4) no . 3_656
H3 O1 3.19(3) no . 4_554
H3 N1 2.88(3) no . 1_655
H3 N1 3.30(3) no . 4_555
H3 N2 3.31(3) no . 2_556
H3 N2 2.64(3) no . 2_656
H3 N2 3.50(3) no . 3_656
H3 C1 2.87(3) no . 1_655
H3 C2 3.48(3) no . 1_655
H3 C3 3.15(3) no . 3_656
H3 H1 2.81(4) no . 2_656
H3 H2 2.42(4) no . 2_556
H3 H2 2.32(4) no . 2_656
H3 H4 3.20(4) no . 1_655
H3 H4 2.46(4) no . 4_555
H3 H4 3.44(4) no . 4_655
H4 O1 2.49(3) no . 4_554
H4 N1 2.79(3) no . 4_554
H4 N2 3.29(3) no . 2_556
H4 N2 3.48(3) no . 2_656
H4 N2 3.15(3) no . 3_656
H4 C1 3.44(3) no . 4_554
H4 C2 3.22(3) no . 4_554
H4 C3 3.36(3) no . 3_656
H4 H1 3.44(4) no . 2_556
H4 H1 3.26(4) no . 2_656
H4 H1 3.50(4) no . 3_656
H4 H2 2.45(4) no . 2_556
H4 H2 3.29(4) no . 2_656
H4 H2 3.37(4) no . 3_656
H4 H3 3.20(4) no . 1_455
H4 H3 3.44(4) no . 4_454
H4 H3 2.46(4) no . 4_554
H4 H4 3.54(4) no . 4_554
H4 H4 3.54(4) no . 4_555

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H3 O1 . . . 2.704(2) 0.95(3) 2.40(3) 98.0(19) no
N1 H4 N2 . . 3_556 2.926(3) 0.88(3) 2.56(3) 105.9(19) no
N2 H1 O1 . . . 2.687(2) 0.83(3) 2.34(3) 106(2) no
N2 H1 O1 . . 3_657 2.954(2) 0.83(3) 2.22(3) 146(2) no
N2 H2 N1 . . 2_546 3.060(3) 0.93(3) 2.14(3) 170(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_DMABQ1
_database_code_depnum_ccdc_archive 'CCDC 1409347'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H24 N4 O2'
_chemical_formula_moiety         'C14 H24 N4 O2'
_chemical_formula_weight         280.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.76606(19)
_cell_length_b                   8.25767(15)
_cell_length_c                   17.3938(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1546.35(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6668
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      67.98
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       heagonalplate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.00
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.935

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15981
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_theta_max         68.130
_diffrn_reflns_theta_min         5.086
_diffrn_reflns_theta_full        68.130
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1410
_reflns_number_gt                1337
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1410
_refine_ls_number_parameters     91
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0686P)²+0.5901P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41472(9) 0.20681(12) 0.10303(5) 0.0265(3) Uani 1 8 d . . .
N1 N 0.46853(10) -0.10083(14) 0.15759(6) 0.0202(3) Uani 1 8 d . . .
N2 N 0.41358(11) 0.30765(14) -0.04562(6) 0.0238(3) Uani 1 8 d . . .
C1 C 0.47929(11) -0.05823(16) 0.07885(7) 0.0177(3) Uani 1 8 d . . .
C2 C 0.44454(12) 0.10502(16) 0.05483(7) 0.0185(3) Uani 1 8 d . . .
C3 C 0.45783(11) 0.15733(16) -0.02847(7) 0.0183(3) Uani 1 8 d . . .
C4 C 0.57275(14) -0.0509(2) 0.20507(8) 0.0321(4) Uani 1 8 d . . .
C5 C 0.34786(13) -0.07872(18) 0.19395(7) 0.0263(3) Uani 1 8 d . . .
C6 C 0.46679(16) 0.41091(17) -0.10517(9) 0.0317(4) Uani 1 8 d . . .
C7 C 0.29377(14) 0.36395(19) -0.01700(9) 0.0322(4) Uani 1 8 d . . .
H4A H 0.56781 -0.10378 0.25413 0.0385 Uiso 1 8 calc R . .
H4B H 0.57021 0.06431 0.21227 0.0385 Uiso 1 8 calc R . .
H4C H 0.6491 -0.08025 0.18019 0.0385 Uiso 1 8 calc R . .
H5A H 0.33663 0.03345 0.20667 0.0315 Uiso 1 8 calc R . .
H5B H 0.34383 -0.14272 0.23996 0.0315 Uiso 1 8 calc R . .
H5C H 0.28357 -0.11233 0.15919 0.0315 Uiso 1 8 calc R . .
H6A H 0.45878 0.52236 -0.09026 0.0381 Uiso 1 8 calc R . .
H6B H 0.42355 0.39343 -0.15272 0.0381 Uiso 1 8 calc R . .
H6C H 0.55305 0.38491 -0.11171 0.0381 Uiso 1 8 calc R . .
H7A H 0.24093 0.39055 -0.05962 0.0386 Uiso 1 8 calc R . .
H7B H 0.30581 0.4583 0.01438 0.0386 Uiso 1 8 calc R . .
H7C H 0.25573 0.28005 0.01309 0.0386 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C2 1.2298(16) yes . .
N1 C1 1.4188(16) yes . .
N1 C4 1.4529(18) yes . .
N1 C5 1.4564(17) yes . .
N2 C3 1.3626(17) yes . .
N2 C6 1.4588(19) yes . .
N2 C7 1.4587(19) yes . .
C1 C2 1.4601(19) yes . .
C1 C3 1.3769(18) yes . 5_655
C2 C3 1.5187(17) yes . .
C4 H4A 0.960 no . .
C4 H4B 0.960 no . .
C4 H4C 0.960 no . .
C5 H5A 0.960 no . .
C5 H5B 0.960 no . .
C5 H5C 0.960 no . .
C6 H6A 0.960 no . .
C6 H6B 0.960 no . .
C6 H6C 0.960 no . .
C7 H7A 0.960 no . .
C7 H7B 0.960 no . .
C7 H7C 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C4 114.54(11) yes . . .
C1 N1 C5 117.45(10) yes . . .
C4 N1 C5 113.98(10) yes . . .
C3 N2 C6 123.41(11) yes . . .
C3 N2 C7 121.65(11) yes . . .
C6 N2 C7 113.78(12) yes . . .
N1 C1 C2 118.96(11) yes . . .
N1 C1 C3 120.47(12) yes . . 5_655
C2 C1 C3 119.51(11) yes . . 5_655
O1 C2 C1 120.19(11) yes . . .
O1 C2 C3 118.72(12) yes . . .
C1 C2 C3 120.76(11) yes . . .
N2 C3 C1 125.03(11) yes . . 5_655
N2 C3 C2 115.79(11) yes . . .
C1 C3 C2 118.98(11) yes 5_655 . .
N1 C4 H4A 109.474 no . . .
N1 C4 H4B 109.475 no . . .
N1 C4 H4C 109.472 no . . .
H4A C4 H4B 109.465 no . . .
H4A C4 H4C 109.468 no . . .
H4B C4 H4C 109.474 no . . .
N1 C5 H5A 109.475 no . . .
N1 C5 H5B 109.469 no . . .
N1 C5 H5C 109.475 no . . .
H5A C5 H5B 109.472 no . . .
H5A C5 H5C 109.469 no . . .
H5B C5 H5C 109.467 no . . .
N2 C6 H6A 109.466 no . . .
N2 C6 H6B 109.476 no . . .
N2 C6 H6C 109.470 no . . .
H6A C6 H6B 109.470 no . . .
H6A C6 H6C 109.470 no . . .
H6B C6 H6C 109.476 no . . .
N2 C7 H7A 109.477 no . . .
N2 C7 H7B 109.468 no . . .
N2 C7 H7C 109.468 no . . .
H7A C7 H7B 109.474 no . . .
H7A C7 H7C 109.472 no . . .
H7B C7 H7C 109.469 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 C1 C2 -82.60(14) no . . . .
C4 N1 C1 C3 85.62(14) no . . . 5_655
C5 N1 C1 C2 55.19(15) no . . . .
C5 N1 C1 C3 -136.60(11) no . . . 5_655
C6 N2 C3 C1 -26.15(19) no . . . 5_655
C6 N2 C3 C2 148.54(11) no . . . .
C7 N2 C3 C1 140.80(12) no . . . 5_655
C7 N2 C3 C2 -44.51(16) no . . . .
N1 C1 C2 O1 4.97(17) no . . . .
N1 C1 C2 C3 178.34(9) no . . . .
N1 C1 C3 N2 7.49(18) no . . 5_655 5_655
N1 C1 C3 C2 -177.98(9) no . . 5_655 5_655
C2 C1 C3 N2 175.64(10) no . . 5_655 5_655
C2 C1 C3 C2 -9.83(17) no . . 5_655 5_655
C3 C1 C2 O1 -163.36(11) no 5_655 . . .
C3 C1 C2 C3 10.01(17) no 5_655 . . .
O1 C2 C3 N2 -11.52(16) no . . . .
O1 C2 C3 C1 163.50(11) no . . . 5_655
C1 C2 C3 N2 175.01(10) no . . . .
C1 C2 C3 C1 -9.96(17) no . . . 5_655

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.7730(15) no . .
O1 N2 2.7164(14) no . .
O1 C1 3.5799(15) no . 5_655
O1 C3 3.5505(16) no . 5_655
O1 C4 3.2517(19) no . .
O1 C5 2.9289(17) no . .
O1 C7 2.7818(18) no . .
N1 N2 2.8846(16) no . 5_655
N1 C6 2.8058(18) no . 5_655
N2 C4 3.4941(19) no . 5_655
C1 C1 2.9407(17) no . 5_655
C1 C6 3.0047(19) no . 5_655
C2 C2 2.8412(18) no . 5_655
C2 C4 3.2237(19) no . .
C2 C5 3.0399(18) no . .
C2 C7 2.961(2) no . .
C3 C3 2.9252(18) no . 5_655
C3 C4 3.2119(19) no . 5_655
C4 C6 3.470(2) no . 5_655
O1 C6 3.4050(18) no . 5_665
C1 C7 3.4402(19) no . 2_545
C2 C7 3.479(2) no . 2_545
C4 C5 3.451(2) no . 8_555
C5 C4 3.451(2) no . 8_455
C6 O1 3.4050(18) no . 5_665
C7 C1 3.4402(19) no . 2_555
C7 C2 3.479(2) no . 2_555
O1 H4B 2.7924 no . .
O1 H5A 2.4507 no . .
O1 H5C 3.1453 no . .
O1 H7B 2.8399 no . .
O1 H7C 2.3965 no . .
N1 H6B 2.6824 no . 5_655
N1 H6C 2.4887 no . 5_655
N2 H4C 3.0758 no . 5_655
C1 H4A 3.2163 no . .
C1 H4B 2.7143 no . .
C1 H4C 2.5461 no . .
C1 H5A 2.8062 no . .
C1 H5B 3.2352 no . .
C1 H5C 2.5676 no . .
C1 H6B 3.2260 no . 5_655
C1 H6C 2.7794 no . 5_655
C2 H4B 3.0729 no . .
C2 H4C 3.4562 no . .
C2 H5A 2.9452 no . .
C2 H5C 3.0854 no . .
C2 H7B 3.3521 no . .
C2 H7C 2.5977 no . .
C3 H4C 2.9487 no . 5_655
C3 H6A 3.2002 no . .
C3 H6B 2.9339 no . .
C3 H6C 2.5844 no . .
C3 H7A 3.0750 no . .
C3 H7B 3.0677 no . .
C3 H7C 2.5067 no . .
C4 H5A 2.6359 no . .
C4 H5B 2.6490 no . .
C4 H5C 3.2538 no . .
C4 H6B 2.9717 no . 5_655
C4 H6C 3.4754 no . 5_655
C5 H4A 2.5973 no . .
C5 H4B 2.6883 no . .
C5 H4C 3.2520 no . .
C5 H6C 3.0947 no . 5_655
C6 H4C 3.2734 no . 5_655
C6 H7A 2.5630 no . .
C6 H7B 2.7351 no . .
C6 H7C 3.2499 no . .
C7 H6A 2.5477 no . .
C7 H6B 2.7540 no . .
C7 H6C 3.2459 no . .
H4A H5A 2.8566 no . .
H4A H5B 2.4452 no . .
H4A H5C 3.4780 no . .
H4A H6B 2.9734 no . 5_655
H4B H5A 2.5295 no . .
H4B H5B 3.0157 no . .
H4B H5C 3.5360 no . .
H4C H5A 3.5229 no . .
H4C H5B 3.4855 no . .
H4C H6B 2.7438 no . 5_655
H4C H6C 3.5333 no . 5_655
H4C H7A 3.5165 no . 5_655
H5B H6B 3.5862 no . 5_655
H5B H6C 3.1951 no . 5_655
H5C H6C 2.9736 no . 5_655
H6A H7A 2.6400 no . .
H6A H7B 2.5109 no . .
H6A H7C 3.4661 no . .
H6B H7A 2.5472 no . .
H6B H7B 3.2158 no . .
H6B H7C 3.5297 no . .
H6C H7A 3.4806 no . .
H6C H7B 3.5018 no . .
O1 H4A 2.9419 no . 7_655
O1 H5C 2.7825 no . 2_555
O1 H6A 2.6279 no . 5_665
O1 H6C 3.3926 no . 5_665
O1 H7B 3.4965 no . 2_545
N1 H4B 3.5978 no . 7_645
N2 H6A 3.0732 no . 5_665
C1 H7A 3.4060 no . 2_545
C1 H7A 3.1565 no . 6_555
C1 H7B 3.2707 no . 2_545
C1 H7C 3.0812 no . 2_545
C2 H6A 3.3062 no . 5_665
C2 H7A 3.3297 no . 2_545
C2 H7A 3.1923 no . 6_555
C2 H7B 3.0377 no . 2_545
C2 H7C 3.5181 no . 2_545
C3 H6A 3.4738 no . 5_665
C3 H7A 3.1186 no . 2_545
C3 H7A 3.4342 no . 6_555
C3 H7B 3.3635 no . 2_545
C3 H7C 3.2596 no . 6_555
C4 H5A 3.3035 no . 8_555
C4 H5B 3.1633 no . 8_555
C4 H5C 3.3141 no . 8_555
C4 H6B 3.2233 no . 3_555
C4 H6C 3.4756 no . 3_555
C4 H7A 3.3812 no . 6_555
C5 H4A 3.1542 no . 8_455
C5 H4B 3.4825 no . 7_645
C5 H4C 3.0613 no . 8_455
C5 H6B 3.1809 no . 3_555
C5 H7B 3.5477 no . 2_545
C5 H7C 3.5356 no . 2_545
C6 H4A 3.1159 no . 3_554
C6 H4B 3.3712 no . 3_554
C6 H5A 3.5897 no . 3_554
C6 H5B 3.5599 no . 3_554
C6 H6A 3.5356 no . 5_665
C6 H7B 3.1071 no . 5_665
C7 H5C 3.1817 no . 2_555
C7 H6A 3.3852 no . 5_665
C7 H6C 3.4688 no . 5_665
C7 H7B 3.5592 no . 2_545
C7 H7C 3.5163 no . 2_555
H4A O1 2.9419 no . 7_645
H4A C5 3.1542 no . 8_555
H4A C6 3.1159 no . 3_555
H4A H4B 3.1720 no . 7_645
H4A H5A 3.2399 no . 7_645
H4A H5A 3.1820 no . 8_555
H4A H5B 2.9908 no . 8_555
H4A H5C 2.7702 no . 8_555
H4A H6A 3.0259 no . 3_555
H4A H6B 2.8380 no . 3_555
H4A H6C 2.9559 no . 3_555
H4B N1 3.5978 no . 7_655
H4B C5 3.4825 no . 7_655
H4B C6 3.3712 no . 3_555
H4B H4A 3.1720 no . 7_655
H4B H5A 3.2062 no . 8_555
H4B H5B 2.7202 no . 7_655
H4B H5B 3.5058 no . 8_555
H4B H5C 3.5218 no . 8_555
H4B H6B 2.8512 no . 3_555
H4B H6C 3.0958 no . 3_555
H4B H7A 3.2507 no . 6_555
H4C C5 3.0613 no . 8_555
H4C H5A 2.9716 no . 8_555
H4C H5B 2.5672 no . 8_555
H4C H5C 3.1577 no . 8_555
H4C H6B 3.3673 no . 6_555
H4C H7A 2.7981 no . 6_555
H5A C4 3.3035 no . 8_455
H5A C6 3.5897 no . 3_555
H5A H4A 3.2399 no . 7_655
H5A H4A 3.1820 no . 8_455
H5A H4B 3.2062 no . 8_455
H5A H4C 2.9716 no . 8_455
H5A H5B 3.3557 no . 2_555
H5A H5C 3.3034 no . 2_555
H5A H6B 2.6874 no . 3_555
H5A H6C 3.5361 no . 6_455
H5B C4 3.1633 no . 8_455
H5B C6 3.5599 no . 3_555
H5B H4A 2.9908 no . 8_455
H5B H4B 2.7202 no . 7_645
H5B H4B 3.5058 no . 8_455
H5B H4C 2.5672 no . 8_455
H5B H5A 3.3557 no . 2_545
H5B H6A 3.3526 no . 3_555
H5B H6B 2.9084 no . 3_555
H5C O1 2.7825 no . 2_545
H5C C4 3.3141 no . 8_455
H5C C7 3.1817 no . 2_545
H5C H4A 2.7702 no . 8_455
H5C H4B 3.5218 no . 8_455
H5C H4C 3.1577 no . 8_455
H5C H5A 3.3034 no . 2_545
H5C H6C 3.2199 no . 6_455
H5C H7B 2.7587 no . 2_545
H5C H7C 2.7252 no . 2_545
H6A O1 2.6279 no . 5_665
H6A N2 3.0732 no . 5_665
H6A C2 3.3062 no . 5_665
H6A C3 3.4738 no . 5_665
H6A C6 3.5356 no . 5_665
H6A C7 3.3852 no . 5_665
H6A H4A 3.0259 no . 3_554
H6A H5B 3.3527 no . 3_554
H6A H6A 3.2838 no . 5_665
H6A H6C 3.5978 no . 5_665
H6A H7B 2.8620 no . 5_665
H6B C4 3.2233 no . 3_554
H6B C5 3.1809 no . 3_554
H6B H4A 2.8380 no . 3_554
H6B H4B 2.8512 no . 3_554
H6B H4C 3.3673 no . 6_455
H6B H5A 2.6874 no . 3_554
H6B H5B 2.9084 no . 3_554
H6C O1 3.3926 no . 5_665
H6C C4 3.4756 no . 3_554
H6C C7 3.4688 no . 5_665
H6C H4A 2.9559 no . 3_554
H6C H4B 3.0958 no . 3_554
H6C H5A 3.5361 no . 6_555
H6C H5C 3.2199 no . 6_555
H6C H6A 3.5978 no . 5_665
H6C H7B 2.6175 no . 5_665
H6C H7C 3.0918 no . 6_555
H7A C1 3.4060 no . 2_555
H7A C1 3.1565 no . 6_455
H7A C2 3.3297 no . 2_555
H7A C2 3.1923 no . 6_455
H7A C3 3.1186 no . 2_555
H7A C3 3.4342 no . 6_455
H7A C4 3.3812 no . 6_455
H7A H4B 3.2507 no . 6_455
H7A H4C 2.7981 no . 6_455
H7A H7C 3.4563 no . 2_555
H7B O1 3.4965 no . 2_555
H7B C1 3.2707 no . 2_555
H7B C2 3.0377 no . 2_555
H7B C3 3.3635 no . 2_555
H7B C5 3.5477 no . 2_555
H7B C6 3.1071 no . 5_665
H7B C7 3.5592 no . 2_555
H7B H5C 2.7587 no . 2_555
H7B H6A 2.8620 no . 5_665
H7B H6C 2.6175 no . 5_665
H7B H7C 2.7384 no . 2_555
H7C C1 3.0812 no . 2_555
H7C C2 3.5181 no . 2_555
H7C C3 3.2596 no . 6_455
H7C C5 3.5356 no . 2_555
H7C C7 3.5163 no . 2_545
H7C H5C 2.7252 no . 2_555
H7C H6C 3.0918 no . 6_455
H7C H7A 3.4563 no . 2_545
H7C H7B 2.7384 no . 2_545
####################################################################### 
# 
# 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_BTABQ4
_database_code_depnum_ccdc_archive 'CCDC 1506326'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C6 H6 N6 O4'
_chemical_formula_moiety         'C6 H6 N6 O4'
_chemical_formula_weight         226.15
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_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
#------------------------------------------------------------------------------
_cell_length_a                   3.68405(13)
_cell_length_b                   13.8967(4)
_cell_length_c                   8.7734(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.475(2)
_cell_angle_gamma                90.0000
_cell_volume                     440.18(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2132
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      68.05
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232.00
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.950

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4625
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         6.052
_diffrn_reflns_theta_full        68.170
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             813
_reflns_number_gt                701
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1878
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         813
_refine_ls_number_parameters     81
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1181P)²+0.5863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5348(6) 0.18145(14) 0.6292(2) 0.0272(6) Uani 1 4 d . . .
O2 O 1.0689(7) 0.32876(17) 0.4495(3) 0.0384(7) Uani 1 4 d . . .
N1 N 0.7042(7) 0.13995(17) 0.3164(3) 0.0232(7) Uani 1 4 d . . .
N2 N 0.7424(7) 0.08798(18) 0.1921(3) 0.0245(7) Uani 1 4 d . . .
N3 N 0.6657(7) -0.00594(17) 0.2107(3) 0.0232(7) Uani 1 4 d . . .
C1 C 0.5219(8) 0.10040(19) 0.5714(3) 0.0207(7) Uani 1 4 d . . .
C2 C 0.5993(8) 0.07857(19) 0.4173(3) 0.0203(7) Uani 1 4 d . . .
C3 C 0.4265(8) 0.01301(19) 0.6486(3) 0.0203(7) Uani 1 4 d . . .
H1 H 1.293(11) 0.283(3) 0.517(4) 0.044(11) Uiso 1 4 d . . .
H2 H 0.894(12) 0.282(3) 0.373(5) 0.048(12) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.232(3) yes . .
N1 N2 1.338(3) yes . .
N1 C2 1.340(4) yes . .
N2 N3 1.352(3) yes . .
N3 C3 1.347(4) yes . 3_656
C1 C2 1.468(4) yes . .
C1 C3 1.467(4) yes . .
C2 C3 1.394(4) yes . 3_656
O2 H1 1.12(4) no . .
O2 H2 1.05(4) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 N1 C2 106.6(2) yes . . .
N1 N2 N3 111.4(2) yes . . .
N2 N3 C3 106.1(2) yes . . 3_656
O1 C1 C2 124.7(3) yes . . .
O1 C1 C3 124.0(3) yes . . .
C2 C1 C3 111.3(2) yes . . .
N1 C2 C1 127.7(2) yes . . .
N1 C2 C3 108.1(3) yes . . 3_656
C1 C2 C3 124.2(3) yes . . 3_656
N3 C3 C1 127.6(2) yes 3_656 . .
N3 C3 C2 107.8(2) yes 3_656 . 3_656
C1 C3 C2 124.5(3) yes . . 3_656
H1 O2 H2 106(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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 180.0(2) no . . . .
N2 N1 C2 C3 -0.1(3) no . . . 3_656
C2 N1 N2 N3 -0.2(3) no . . . .
N1 N2 N3 C3 0.4(3) no . . . 3_656
N2 N3 C3 C1 -177.9(2) no . . 3_656 3_656
N2 N3 C3 C2 -0.4(3) no . . 3_656 .
O1 C1 C2 N1 1.9(4) no . . . .
O1 C1 C2 C3 -178.1(2) no . . . 3_656
O1 C1 C3 N3 1.1(4) no . . . 3_656
O1 C1 C3 C2 178.1(2) no . . . 3_656
C2 C1 C3 N3 -178.9(2) no . . . 3_656
C2 C1 C3 C2 -1.9(4) no . . . 3_656
C3 C1 C2 N1 -178.1(2) no . . . .
C3 C1 C2 C3 1.9(4) no . . . 3_656
N1 C2 C3 N3 0.3(3) no . . 3_656 .
N1 C2 C3 C1 177.8(2) no . . 3_656 3_656
C1 C2 C3 N3 -179.7(2) no . . 3_656 .
C1 C2 C3 C1 -2.2(4) no . . 3_656 3_656

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.989(3) no . .
O1 N3 2.980(3) no . 3_656
N2 C1 3.583(4) no . .
N2 C1 3.593(4) no . 3_656
C1 C1 3.050(4) no . 3_656
C2 C2 2.798(4) no . 3_656
C3 C3 2.791(4) no . 3_656
O1 O2 2.923(3) no . 1_455
O1 O2 3.432(4) no . .
O1 O2 3.575(4) no . 4_455
O1 O2 3.097(3) no . 4_555
O1 N1 2.973(3) no . 4_555
O1 N2 3.315(3) no . 4_555
O2 O1 3.432(4) no . .
O2 O1 2.923(3) no . 1_655
O2 O1 3.097(3) no . 4_554
O2 O1 3.575(4) no . 4_654
O2 N1 3.071(3) no . .
O2 N2 2.887(4) no . 4_555
O2 N2 3.150(3) no . 4_655
O2 N3 2.959(4) no . 2_755
N1 O1 2.973(3) no . 4_554
N1 O2 3.071(3) no . .
N1 N2 3.567(3) no . 1_455
N1 C1 3.421(3) no . 1_655
N1 C2 3.350(4) no . 1_655
N2 O1 3.315(3) no . 4_554
N2 O2 3.150(3) no . 4_454
N2 O2 2.887(4) no . 4_554
N2 N1 3.567(3) no . 1_655
N2 C2 3.377(3) no . 1_655
N2 C3 3.405(4) no . 3_756
N3 O2 2.959(4) no . 2_745
N3 C1 3.473(3) no . 3_756
N3 C3 3.328(4) no . 3_756
C1 N1 3.421(3) no . 1_455
C1 N3 3.473(3) no . 3_756
C1 C2 3.412(4) no . 1_455
C1 C3 3.484(4) no . 1_655
C2 N1 3.350(4) no . 1_455
C2 N2 3.377(3) no . 1_455
C2 C1 3.412(4) no . 1_655
C2 C3 3.431(4) no . 1_655
C3 N2 3.405(4) no . 3_756
C3 N3 3.328(4) no . 3_756
C3 C1 3.484(4) no . 1_455
C3 C2 3.431(4) no . 1_455
O1 H1 1.84(4) no . 1_455
O1 H1 3.44(4) no . .
O1 H2 3.23(4) no . 1_455
O1 H2 3.15(5) no . .
O1 H2 3.52(5) no . 4_455
O1 H2 2.34(4) no . 4_555
O2 H1 3.10(4) no . 1_455
O2 H2 3.30(5) no . 1_655
N1 H1 3.22(4) no . 1_455
N1 H1 3.19(4) no . .
N1 H1 2.96(4) no . 4_454
N1 H2 2.12(4) no . .
N2 H1 2.71(4) no . 4_454
N2 H1 3.31(4) no . 4_554
N2 H2 3.12(4) no . .
N2 H2 3.47(5) no . 4_554
N3 H1 3.57(4) no . 2_745
N3 H2 3.59(4) no . 2_645
N3 H2 3.51(4) no . 2_745
C1 H1 2.68(4) no . 1_455
C1 H2 3.50(4) no . .
C1 H2 3.18(4) no . 4_555
C2 H1 3.23(4) no . 1_455
C2 H2 3.08(4) no . .
H1 O1 3.44(4) no . .
H1 O1 1.84(4) no . 1_655
H1 O2 3.10(4) no . 1_655
H1 N1 3.19(4) no . .
H1 N1 3.22(4) no . 1_655
H1 N1 2.96(4) no . 4_655
H1 N2 3.31(4) no . 4_555
H1 N2 2.71(4) no . 4_655
H1 N3 3.57(4) no . 2_755
H1 C1 2.68(4) no . 1_655
H1 C2 3.23(4) no . 1_655
H1 H2 2.76(6) no . 1_655
H1 H2 3.57(5) no . 4_655
H2 O1 3.15(5) no . .
H2 O1 3.23(4) no . 1_655
H2 O1 2.34(4) no . 4_554
H2 O1 3.52(5) no . 4_654
H2 O2 3.30(5) no . 1_455
H2 N1 2.12(4) no . .
H2 N2 3.12(4) no . .
H2 N2 3.47(5) no . 4_555
H2 N3 3.59(4) no . 2_655
H2 N3 3.51(4) no . 2_755
H2 C1 3.50(4) no . .
H2 C1 3.18(4) no . 4_554
H2 C2 3.08(4) no . .
H2 H1 2.76(6) no . 1_455
H2 H1 3.57(5) no . 4_454

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H1 O1 . . 1_655 2.923(3) 1.12(4) 1.84(4) 162(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_BTABQ-DiPA
_database_code_depnum_ccdc_archive 'CCDC 1506327'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H32 N8 O2'
_chemical_formula_moiety         'C18 H32 N8 O2'
_chemical_formula_weight         392.50
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5718(3)
_cell_length_b                   8.46267(18)
_cell_length_c                   8.7904(2)
_cell_angle_alpha                102.0567(14)
_cell_angle_beta                 102.4887(18)
_cell_angle_gamma                101.2122(18)
_cell_volume                     520.60(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2712
_cell_measurement_theta_min      5.34
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212.00
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_T_max  0.972

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            5687
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         5.341
_diffrn_reflns_theta_full        68.220
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1866
_reflns_number_gt                1492
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1301
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     191
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0811P)²+0.0409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21285(18) 0.77816(15) 0.43036(15) 0.0309(4) Uani 1 2 d . . .
N1 N 0.2960(2) 1.01997(19) 0.74792(18) 0.0283(4) Uani 1 2 d . . .
N2 N 0.2793(2) 1.14644(18) 0.86225(17) 0.0289(4) Uani 1 2 d . . .
N3 N 0.1327(2) 1.20582(19) 0.80852(17) 0.0293(4) Uani 1 2 d . . .
N4 N 0.4414(2) 0.74952(19) 0.83676(18) 0.0261(4) Uani 1 2 d . . .
C1 C 0.1159(3) 0.8747(2) 0.4593(2) 0.0260(5) Uani 1 2 d . . .
C2 C 0.1557(3) 0.9985(2) 0.6165(2) 0.0242(4) Uani 1 2 d . . .
C3 C -0.0530(3) 0.8862(2) 0.3462(2) 0.0254(4) Uani 1 2 d . . .
C4 C 0.5221(3) 0.6645(2) 0.7091(2) 0.0283(5) Uani 1 2 d . . .
C5 C 0.6738(3) 0.7965(3) 0.6861(3) 0.0393(5) Uani 1 2 d . . .
C6 C 0.5951(4) 0.5233(3) 0.7594(3) 0.0345(5) Uani 1 2 d . . .
C7 C 0.2770(3) 0.6453(2) 0.8714(2) 0.0284(5) Uani 1 2 d . . .
C8 C 0.1143(3) 0.5756(3) 0.7216(3) 0.0351(5) Uani 1 2 d . . .
C9 C 0.2263(3) 0.7534(3) 1.0086(3) 0.0362(5) Uani 1 2 d . . .
H4 H 0.414(3) 0.620(2) 0.609(2) 0.023(5) Uiso 1 2 d . . .
H5A H 0.780(4) 0.839(3) 0.789(3) 0.057(7) Uiso 1 2 d . . .
H5B H 0.732(3) 0.747(3) 0.603(3) 0.044(6) Uiso 1 2 d . . .
H5C H 0.626(3) 0.891(3) 0.659(3) 0.052(7) Uiso 1 2 d . . .
H6A H 0.691(3) 0.565(3) 0.862(3) 0.038(6) Uiso 1 2 d . . .
H6B H 0.498(3) 0.433(3) 0.766(3) 0.043(6) Uiso 1 2 d . . .
H6C H 0.659(3) 0.472(3) 0.679(2) 0.039(6) Uiso 1 2 d . . .
H7 H 0.321(3) 0.552(2) 0.910(2) 0.028(5) Uiso 1 2 d . . .
H8A H 0.014(3) 0.510(3) 0.743(2) 0.043(6) Uiso 1 2 d . . .
H8B H 0.066(3) 0.668(3) 0.685(3) 0.051(7) Uiso 1 2 d . . .
H8C H 0.150(3) 0.500(3) 0.630(3) 0.051(7) Uiso 1 2 d . . .
H9A H 0.184(3) 0.840(3) 0.975(3) 0.045(6) Uiso 1 2 d . . .
H9B H 0.121(3) 0.687(3) 1.040(3) 0.054(7) Uiso 1 2 d . . .
H9C H 0.333(3) 0.796(3) 1.106(3) 0.049(6) Uiso 1 2 d . . .
H4A H 0.543(3) 0.794(3) 0.942(3) 0.039(6) Uiso 1 2 d . . .
H4B H 0.406(3) 0.843(3) 0.808(3) 0.050(7) Uiso 1 2 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.224(3) yes . .
N1 N2 1.353(2) yes . .
N1 C2 1.343(2) yes . .
N2 N3 1.340(2) yes . .
N3 C3 1.356(2) yes . 2_576
N4 C4 1.510(3) yes . .
N4 C7 1.507(3) yes . .
C1 C2 1.480(2) yes . .
C1 C3 1.474(3) yes . .
C2 C3 1.391(3) yes . 2_576
C4 C5 1.518(3) yes . .
C4 C6 1.517(3) yes . .
C7 C8 1.514(3) yes . .
C7 C9 1.521(3) yes . .
N4 H4A 1.010(19) no . .
N4 H4B 0.94(3) no . .
C4 H4 1.008(17) no . .
C5 H5A 1.01(2) no . .
C5 H5B 0.99(3) no . .
C5 H5C 0.99(3) no . .
C6 H6A 0.97(2) no . .
C6 H6B 0.97(2) no . .
C6 H6C 1.02(2) no . .
C7 H7 1.01(2) no . .
C8 H8A 0.93(2) no . .
C8 H8B 1.01(3) no . .
C8 H8C 1.04(3) no . .
C9 H9A 0.93(3) no . .
C9 H9B 1.01(3) no . .
C9 H9C 0.99(2) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 N1 C2 106.26(16) yes . . .
N1 N2 N3 111.87(13) yes . . .
N2 N3 C3 105.62(15) yes . . 2_576
C4 N4 C7 117.23(13) yes . . .
O1 C1 C2 123.49(16) yes . . .
O1 C1 C3 125.94(15) yes . . .
C2 C1 C3 110.58(17) yes . . .
N1 C2 C1 126.49(18) yes . . .
N1 C2 C3 107.87(15) yes . . 2_576
C1 C2 C3 125.64(16) yes . . 2_576
N3 C3 C1 127.84(18) yes 2_576 . .
N3 C3 C2 108.38(16) yes 2_576 . 2_576
C1 C3 C2 123.76(15) yes . . 2_576
N4 C4 C5 107.53(15) yes . . .
N4 C4 C6 109.98(17) yes . . .
C5 C4 C6 112.5(2) yes . . .
N4 C7 C8 111.09(17) yes . . .
N4 C7 C9 108.00(15) yes . . .
C8 C7 C9 112.14(19) yes . . .
C4 N4 H4A 108.6(15) no . . .
C4 N4 H4B 108.8(15) no . . .
C7 N4 H4A 106.8(14) no . . .
C7 N4 H4B 108.2(15) no . . .
H4A N4 H4B 106.7(17) no . . .
N4 C4 H4 104.7(13) no . . .
C5 C4 H4 111.0(12) no . . .
C6 C4 H4 110.8(11) no . . .
C4 C5 H5A 109.0(16) no . . .
C4 C5 H5B 110.8(13) no . . .
C4 C5 H5C 111.8(14) no . . .
H5A C5 H5B 104(2) no . . .
H5A C5 H5C 109.7(19) no . . .
H5B C5 H5C 111(2) no . . .
C4 C6 H6A 110.7(14) no . . .
C4 C6 H6B 113.6(16) no . . .
C4 C6 H6C 110.5(13) no . . .
H6A C6 H6B 109.8(19) no . . .
H6A C6 H6C 105.3(19) no . . .
H6B C6 H6C 106.6(18) no . . .
N4 C7 H7 106.7(12) no . . .
C8 C7 H7 110.5(9) no . . .
C9 C7 H7 108.2(12) no . . .
C7 C8 H8A 110.8(13) no . . .
C7 C8 H8B 111.0(10) no . . .
C7 C8 H8C 111.3(13) no . . .
H8A C8 H8B 105(2) no . . .
H8A C8 H8C 106.7(19) no . . .
H8B C8 H8C 111(2) no . . .
C7 C9 H9A 109.7(15) no . . .
C7 C9 H9B 110.7(13) no . . .
C7 C9 H9C 111.1(16) no . . .
H9A C9 H9B 107(2) no . . .
H9A C9 H9C 111.8(19) no . . .
H9B C9 H9C 107(2) 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 179.69(15) no . . . .
N2 N1 C2 C3 -0.36(19) no . . . 2_576
C2 N1 N2 N3 0.3(2) no . . . .
N1 N2 N3 C3 -0.09(19) no . . . 2_576
N2 N3 C3 C1 178.35(16) no . . 2_576 2_576
N2 N3 C3 C2 -0.14(19) no . . 2_576 .
C4 N4 C7 C8 -59.5(2) no . . . .
C4 N4 C7 C9 177.15(14) no . . . .
C7 N4 C4 C5 175.38(14) no . . . .
C7 N4 C4 C6 -61.78(18) no . . . .
O1 C1 C2 N1 -2.0(3) no . . . .
O1 C1 C2 C3 178.09(17) no . . . 2_576
O1 C1 C3 N3 0.2(3) no . . . 2_576
O1 C1 C3 C2 -178.11(17) no . . . 2_576
C2 C1 C3 N3 179.75(17) no . . . 2_576
C2 C1 C3 C2 1.5(3) no . . . 2_576
C3 C1 C2 N1 178.42(16) no . . . .
C3 C1 C2 C3 -1.5(3) no . . . 2_576
N1 C2 C3 N3 0.3(2) no . . 2_576 .
N1 C2 C3 C1 -178.24(16) no . . 2_576 2_576
C1 C2 C3 N3 -179.73(16) no . . 2_576 .
C1 C2 C3 C1 1.7(3) no . . 2_576 2_576

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.9545(18) no . .
O1 N3 3.026(2) no . 2_576
N2 C1 3.600(2) no . .
N2 C1 3.591(2) no . 2_576
C1 C1 3.073(3) no . 2_576
C2 C2 2.777(3) no . 2_576
C3 C3 2.820(2) no . 2_576
C4 C8 3.064(3) no . .
C6 C7 3.067(4) no . .
O1 C4 3.434(2) no . .
O1 C6 3.481(3) no . 2_666
O1 C8 3.494(3) no . .
O1 C8 3.301(2) no . 2_566
N1 N4 2.901(3) no . .
N1 C7 3.546(3) no . .
N1 C9 3.583(3) no . .
N2 N4 2.8514(19) no . 2_677
N2 C7 3.528(2) no . 2_677
N2 C9 3.543(3) no . 2_677
N3 C7 3.554(2) no . 1_565
N3 C8 3.394(3) no . 1_565
N3 C9 3.481(3) no . 2_577
N4 N1 2.901(3) no . .
N4 N2 2.8514(19) no . 2_677
C1 C5 3.544(3) no . 2_676
C4 O1 3.434(2) no . .
C5 C1 3.544(3) no . 2_676
C6 O1 3.481(3) no . 2_666
C7 N1 3.546(3) no . .
C7 N2 3.528(2) no . 2_677
C7 N3 3.554(2) no . 1_545
C8 O1 3.494(3) no . .
C8 O1 3.301(2) no . 2_566
C8 N3 3.394(3) no . 1_545
C9 N1 3.583(3) no . .
C9 N2 3.543(3) no . 2_677
C9 N3 3.481(3) no . 2_577
N4 H5A 2.68(3) no . .
N4 H5B 3.32(3) no . .
N4 H5C 2.62(3) no . .
N4 H6A 2.68(3) no . .
N4 H6B 2.76(3) no . .
N4 H6C 3.37(2) no . .
N4 H8A 3.30(2) no . .
N4 H8B 2.75(2) no . .
N4 H8C 2.736(19) no . .
N4 H9A 2.66(3) no . .
N4 H9B 3.33(3) no . .
N4 H9C 2.65(3) no . .
C4 H7 2.77(2) no . .
C4 H8B 3.42(2) no . .
C4 H8C 2.75(2) no . .
C5 H6A 2.74(3) no . .
C5 H6B 3.38(3) no . .
C5 H6C 2.72(2) no . .
C5 H4A 2.65(3) no . .
C5 H4B 2.54(3) no . .
C6 H5A 2.69(2) no . .
C6 H5B 2.73(3) no . .
C6 H5C 3.38(3) no . .
C6 H7 2.72(2) no . .
C6 H8C 3.27(2) no . .
C6 H4A 2.66(2) no . .
C6 H4B 3.29(3) no . .
C7 H4 2.71(2) no . .
C7 H6A 3.35(2) no . .
C7 H6B 2.83(3) no . .
C8 H4 2.66(2) no . .
C8 H6B 3.33(3) no . .
C8 H9A 2.68(2) no . .
C8 H9B 2.74(2) no . .
C8 H9C 3.37(2) no . .
C8 H4A 3.340(19) no . .
C8 H4B 2.68(2) no . .
C9 H8A 2.714(18) no . .
C9 H8B 2.72(2) no . .
C9 H8C 3.42(2) no . .
C9 H4A 2.56(3) no . .
C9 H4B 2.59(3) no . .
H4 H5A 2.91(3) no . .
H4 H5B 2.45(3) no . .
H4 H5C 2.42(3) no . .
H4 H6A 2.89(3) no . .
H4 H6B 2.39(3) no . .
H4 H6C 2.48(3) no . .
H4 H7 3.02(3) no . .
H4 H8A 3.51(3) no . .
H4 H8B 2.94(3) no . .
H4 H8C 2.12(3) no . .
H4 H4A 2.84(3) no . .
H4 H4B 2.31(3) no . .
H5A H6A 2.54(4) no . .
H5A H6C 2.95(3) no . .
H5A H4A 2.48(4) no . .
H5A H4B 2.88(4) no . .
H5B H6A 3.04(4) no . .
H5B H6C 2.55(3) no . .
H5B H4A 3.56(4) no . .
H5B H4B 3.47(4) no . .
H5C H4A 2.92(4) no . .
H5C H4B 2.35(4) no . .
H6A H7 2.91(3) no . .
H6A H4A 2.48(3) no . .
H6A H4B 3.52(4) no . .
H6B H7 2.27(3) no . .
H6B H8C 2.86(4) no . .
H6B H4A 3.04(3) no . .
H6C H4A 3.57(3) no . .
H7 H8A 2.38(3) no . .
H7 H8B 2.92(3) no . .
H7 H8C 2.43(3) no . .
H7 H9A 2.82(3) no . .
H7 H9B 2.40(3) no . .
H7 H9C 2.36(3) no . .
H7 H4A 2.31(3) no . .
H7 H4B 2.80(3) no . .
H8A H9A 2.95(3) no . .
H8A H9B 2.59(3) no . .
H8A H4B 3.53(3) no . .
H8B H9A 2.52(3) no . .
H8B H9B 3.02(3) no . .
H8B H4B 2.58(3) no . .
H8C H4B 3.04(3) no . .
H9A H4A 2.88(4) no . .
H9A H4B 2.46(4) no . .
H9B H4A 3.49(4) no . .
H9B H4B 3.53(4) no . .
H9C H4A 2.37(4) no . .
H9C H4B 2.88(4) no . .
O1 H4 2.69(2) no . .
O1 H5C 3.17(2) no . .
O1 H5C 3.16(3) no . 2_676
O1 H6B 3.58(3) no . 2_666
O1 H6C 2.58(2) no . 2_666
O1 H8A 2.625(19) no . 2_566
O1 H8B 2.94(3) no . .
O1 H8C 3.24(3) no . .
O1 H8C 3.12(2) no . 2_566
O1 H9B 3.24(2) no . 1_554
O1 H9C 3.20(3) no . 1_554
O1 H4B 3.21(2) no . .
N1 H5C 3.10(3) no . .
N1 H6B 3.49(2) no . 1_565
N1 H8B 3.01(2) no . .
N1 H9A 2.92(3) no . .
N1 H9C 2.81(2) no . 2_677
N1 H4A 3.38(2) no . .
N1 H4A 2.724(19) no . 2_677
N1 H4B 1.97(3) no . .
N2 H5A 3.18(3) no . 2_677
N2 H6A 2.99(2) no . 2_677
N2 H6B 3.04(3) no . 1_565
N2 H7 3.32(2) no . 1_565
N2 H7 3.453(16) no . 2_677
N2 H9A 2.98(3) no . .
N2 H9C 2.82(3) no . 2_677
N2 H4A 1.85(2) no . 2_677
N2 H4B 2.90(3) no . .
N2 H4B 3.30(2) no . 2_677
N3 H5A 3.57(3) no . 2_677
N3 H6A 2.984(19) no . 2_677
N3 H6B 3.19(2) no . 1_565
N3 H7 2.855(18) no . 1_565
N3 H8A 3.01(3) no . 1_565
N3 H8C 3.21(3) no . 1_565
N3 H9A 3.38(3) no . 2_577
N3 H9B 2.75(3) no . 2_577
N3 H4A 2.92(2) no . 2_677
C1 H5B 3.49(3) no . 1_455
C1 H5B 3.38(2) no . 2_676
C1 H5C 3.01(3) no . 2_676
C1 H8A 3.21(2) no . 2_566
C1 H8B 2.94(3) no . .
C1 H8C 3.24(2) no . 2_566
C1 H4B 3.46(2) no . .
C2 H5B 3.45(2) no . 1_455
C2 H5B 3.29(3) no . 2_676
C2 H5C 3.40(3) no . 2_676
C2 H8B 2.96(3) no . .
C2 H4B 2.95(3) no . .
C3 H5A 3.38(3) no . 2_676
C3 H5B 3.33(3) no . 1_455
C3 H5B 3.43(2) no . 2_676
C3 H5C 3.43(2) no . 2_676
C3 H8A 3.36(2) no . 2_566
C3 H8C 3.27(2) no . 2_566
C3 H9B 3.51(3) no . 1_554
C4 H4 3.476(19) no . 2_666
C4 H6C 3.248(19) no . 2_666
C5 H8B 3.36(3) no . 1_655
C5 H9C 3.57(2) no . 2_677
C6 H4 3.193(19) no . 2_666
C6 H5B 3.584(19) no . 2_666
C6 H7 3.06(2) no . 2_667
C6 H8A 3.23(3) no . 1_655
C6 H9B 3.47(3) no . 2_667
C6 H9C 3.26(3) no . 2_667
C7 H6A 3.22(3) no . 2_667
C7 H6B 3.53(2) no . 2_667
C8 H5B 3.54(3) no . 1_455
C8 H6C 3.30(2) no . 1_455
C8 H8B 3.55(2) no . 2_566
C8 H8C 3.16(2) no . 2_566
C9 H5A 3.55(2) no . 2_677
C9 H5C 3.53(2) no . 2_677
C9 H6A 3.25(2) no . 2_667
C9 H6B 3.40(3) no . 2_667
H4 O1 2.69(2) no . .
H4 C4 3.476(19) no . 2_666
H4 C6 3.193(19) no . 2_666
H4 H4 3.16(3) no . 2_666
H4 H5B 3.11(3) no . 2_666
H4 H6B 3.46(3) no . 2_666
H4 H6C 2.39(3) no . 2_666
H5A N2 3.18(3) no . 2_677
H5A N3 3.57(3) no . 2_677
H5A C3 3.38(3) no . 2_676
H5A C9 3.55(2) no . 2_677
H5A H8A 3.58(4) no . 1_655
H5A H8B 3.02(4) no . 1_655
H5A H9A 3.14(3) no . 1_655
H5A H9A 2.98(3) no . 2_677
H5A H9C 3.37(4) no . 2_677
H5B C1 3.49(3) no . 1_655
H5B C1 3.38(2) no . 2_676
H5B C2 3.45(2) no . 1_655
H5B C2 3.29(3) no . 2_676
H5B C3 3.33(3) no . 1_655
H5B C3 3.43(2) no . 2_676
H5B C6 3.584(19) no . 2_666
H5B C8 3.54(3) no . 1_655
H5B H4 3.11(3) no . 2_666
H5B H6B 3.21(3) no . 2_666
H5B H6C 3.33(3) no . 2_666
H5B H8A 3.42(4) no . 1_655
H5B H8B 2.73(3) no . 1_655
H5B H8C 3.01(4) no . 2_666
H5C O1 3.17(2) no . .
H5C O1 3.16(3) no . 2_676
H5C N1 3.10(3) no . .
H5C C1 3.01(3) no . 2_676
H5C C2 3.40(3) no . 2_676
H5C C3 3.43(2) no . 2_676
H5C C9 3.53(2) no . 2_677
H5C H9A 3.36(3) no . 2_677
H5C H9C 2.92(3) no . 2_677
H6A N2 2.99(2) no . 2_677
H6A N3 2.984(19) no . 2_677
H6A C7 3.22(3) no . 2_667
H6A C9 3.25(2) no . 2_667
H6A H7 2.43(3) no . 2_667
H6A H8A 2.94(4) no . 1_655
H6A H8B 3.57(4) no . 1_655
H6A H9B 3.15(3) no . 1_655
H6A H9B 2.96(4) no . 2_667
H6A H9C 3.10(4) no . 2_667
H6B O1 3.58(3) no . 2_666
H6B N1 3.49(2) no . 1_545
H6B N2 3.04(3) no . 1_545
H6B N3 3.19(2) no . 1_545
H6B C7 3.53(2) no . 2_667
H6B C9 3.40(3) no . 2_667
H6B H4 3.46(3) no . 2_666
H6B H5B 3.21(3) no . 2_666
H6B H7 2.85(3) no . 2_667
H6B H9B 3.46(4) no . 2_667
H6B H9C 2.82(4) no . 2_667
H6B H4A 3.55(4) no . 2_667
H6C O1 2.58(2) no . 2_666
H6C C4 3.248(19) no . 2_666
H6C C8 3.30(2) no . 1_655
H6C H4 2.39(3) no . 2_666
H6C H5B 3.33(3) no . 2_666
H6C H8A 2.56(3) no . 1_655
H6C H8B 3.18(3) no . 1_655
H6C H8C 3.36(4) no . 2_666
H6C H9B 3.34(3) no . 2_667
H6C H9C 3.24(4) no . 2_667
H7 N2 3.32(2) no . 1_545
H7 N2 3.453(16) no . 2_677
H7 N3 2.855(18) no . 1_545
H7 C6 3.06(2) no . 2_667
H7 H6A 2.43(3) no . 2_667
H7 H6B 2.85(3) no . 2_667
H7 H7 3.21(3) no . 2_667
H8A O1 2.625(19) no . 2_566
H8A N3 3.01(3) no . 1_545
H8A C1 3.21(2) no . 2_566
H8A C3 3.36(2) no . 2_566
H8A C6 3.23(3) no . 1_455
H8A H5A 3.58(4) no . 1_455
H8A H5B 3.42(4) no . 1_455
H8A H6A 2.94(4) no . 1_455
H8A H6C 2.56(3) no . 1_455
H8A H8C 3.22(3) no . 2_566
H8A H9B 2.99(4) no . 2_567
H8B O1 2.94(3) no . .
H8B N1 3.01(2) no . .
H8B C1 2.94(3) no . .
H8B C2 2.96(3) no . .
H8B C5 3.36(3) no . 1_455
H8B C8 3.55(2) no . 2_566
H8B H5A 3.02(4) no . 1_455
H8B H5B 2.73(3) no . 1_455
H8B H6A 3.57(4) no . 1_455
H8B H6C 3.18(3) no . 1_455
H8B H8C 2.80(3) no . 2_566
H8C O1 3.24(3) no . .
H8C O1 3.12(2) no . 2_566
H8C N3 3.21(3) no . 1_545
H8C C1 3.24(2) no . 2_566
H8C C3 3.27(2) no . 2_566
H8C C8 3.16(2) no . 2_566
H8C H5B 3.01(4) no . 2_666
H8C H6C 3.36(4) no . 2_666
H8C H8A 3.22(3) no . 2_566
H8C H8B 2.80(3) no . 2_566
H8C H8C 2.85(3) no . 2_566
H9A N1 2.92(3) no . .
H9A N2 2.98(3) no . .
H9A N3 3.38(3) no . 2_577
H9A H5A 3.14(3) no . 1_455
H9A H5A 2.98(3) no . 2_677
H9A H5C 3.36(3) no . 2_677
H9A H4A 3.21(3) no . 2_677
H9A H4B 3.54(3) no . 2_677
H9B O1 3.24(2) no . 1_556
H9B N3 2.75(3) no . 2_577
H9B C3 3.51(3) no . 1_556
H9B C6 3.47(3) no . 2_667
H9B H6A 3.15(3) no . 1_455
H9B H6A 2.96(4) no . 2_667
H9B H6B 3.46(4) no . 2_667
H9B H6C 3.34(3) no . 2_667
H9B H8A 2.99(4) no . 2_567
H9B H9B 3.18(3) no . 2_567
H9C O1 3.20(3) no . 1_556
H9C N1 2.81(2) no . 2_677
H9C N2 2.82(3) no . 2_677
H9C C5 3.57(2) no . 2_677
H9C C6 3.26(3) no . 2_667
H9C H5A 3.37(4) no . 2_677
H9C H5C 2.92(3) no . 2_677
H9C H6A 3.10(4) no . 2_667
H9C H6B 2.82(4) no . 2_667
H9C H6C 3.24(4) no . 2_667
H9C H4A 3.55(3) no . 2_677
H9C H4B 3.14(3) no . 2_677
H4A N1 3.38(2) no . .
H4A N1 2.724(19) no . 2_677
H4A N2 1.85(2) no . 2_677
H4A N3 2.92(2) no . 2_677
H4A H6B 3.55(4) no . 2_667
H4A H9A 3.21(3) no . 2_677
H4A H9C 3.55(3) no . 2_677
H4A H4B 3.28(3) no . 2_677
H4B O1 3.21(2) no . .
H4B N1 1.97(3) no . .
H4B N2 2.90(3) no . .
H4B N2 3.30(2) no . 2_677
H4B C1 3.46(2) no . .
H4B C2 2.95(3) no . .
H4B H9A 3.54(3) no . 2_677
H4B H9C 3.14(3) no . 2_677
H4B H4A 3.28(3) no . 2_677

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4A N2 . . 2_677 2.8514(19) 1.010(19) 1.85(2) 174(2) no
N4 H4B N1 . . . 2.901(3) 0.94(3) 1.97(3) 171(2) 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_BTABQ-per5
_database_code_depnum_ccdc_archive 'CCDC 1506328'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C32 H22 N8 O8'
_chemical_formula_moiety         'C32 H22 N8 O8'
_chemical_formula_weight         646.57
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_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
#------------------------------------------------------------------------------
_cell_length_a                   10.5475
_cell_length_b                   20.4313
_cell_length_c                   6.8444
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.4580
_cell_angle_gamma                90.0000
_cell_volume                     1390.7180
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2360
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      66.69
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668.00
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15700
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_theta_max         68.160
_diffrn_reflns_theta_min         4.328
_diffrn_reflns_theta_full        68.160
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2514
_reflns_number_gt                1911
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1322
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2514
_refine_ls_number_parameters     261
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0544P)²+0.8786P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36086(17) -0.02469(8) 0.6454(3) 0.0439(5) Uani 1 4 d . . .
O2 O -0.00937(17) 0.16938(8) 0.3355(3) 0.0419(5) Uani 1 4 d . . .
O3 O 0.2896(2) -0.16148(10) 0.7329(3) 0.0474(5) Uani 1 4 d . . .
O4 O 0.5865(2) 0.25571(11) 0.4388(3) 0.0476(5) Uani 1 4 d . . .
N1 N 0.4384(2) 0.11151(10) 0.5759(3) 0.0412(5) Uani 1 4 d . . .
N2 N 0.4118(2) 0.17328(11) 0.5122(4) 0.0427(5) Uani 1 4 d . . .
N3 N 0.2836(2) 0.19128(10) 0.4423(3) 0.0413(5) Uani 1 4 d . . .
N4 N 0.0949(2) -0.04962(10) 0.5804(3) 0.0364(5) Uani 1 4 d . . .
C1 C 0.2815(2) 0.01975(12) 0.5830(4) 0.0377(6) Uani 1 4 d . . .
C2 C 0.3151(2) 0.08686(12) 0.5431(4) 0.0379(6) Uani 1 4 d . . .
C3 C 0.2199(2) 0.13603(12) 0.4616(4) 0.0374(6) Uani 1 4 d . . .
C4 C 0.0745(3) 0.12726(12) 0.4088(4) 0.0378(6) Uani 1 4 d . . .
C5 C 0.0367(2) 0.05961(12) 0.4578(4) 0.0358(6) Uani 1 4 d . . .
C6 C 0.1313(2) 0.00998(12) 0.5384(4) 0.0357(6) Uani 1 4 d . . .
C7 C 0.3392(3) 0.07165(14) 0.0614(4) 0.0442(6) Uani 1 4 d . . .
C8 C 0.2601(3) 0.12523(14) -0.0145(4) 0.0448(6) Uani 1 4 d . . .
C9 C 0.1181(3) 0.12079(12) -0.0630(4) 0.0412(6) Uani 1 4 d . . .
C10 C 0.0353(3) 0.17576(13) -0.1406(4) 0.0458(7) Uani 1 4 d . . .
C11 C -0.1010(3) 0.17121(13) -0.1865(5) 0.0472(7) Uani 1 4 d . . .
C12 C -0.1601(3) 0.11237(13) -0.1576(4) 0.0451(7) Uani 1 4 d . . .
C13 C -0.0836(3) 0.05702(12) -0.0804(4) 0.0379(6) Uani 1 4 d . . .
C14 C -0.1445(3) -0.00550(12) -0.0497(4) 0.0383(6) Uani 1 4 d . . .
C15 C -0.2826(3) -0.01249(13) -0.0941(4) 0.0419(6) Uani 1 4 d . . .
C16 C 0.0594(3) 0.06061(12) -0.0307(4) 0.0383(6) Uani 1 4 d . . .
H1C H 0.479(4) 0.2019(18) 0.507(5) 0.075(11) Uiso 1 4 d . . .
H2 H 0.439(3) 0.0762(12) 0.099(4) 0.037(7) Uiso 1 4 d . . .
H3 H 0.299(3) 0.1668(14) -0.031(4) 0.045(7) Uiso 1 4 d . . .
H4 H 0.075(3) 0.2166(16) -0.161(5) 0.055(8) Uiso 1 4 d . . .
H5 H -0.158(3) 0.2083(15) -0.245(5) 0.056(8) Uiso 1 4 d . . .
H6 H -0.259(3) 0.1104(14) -0.191(5) 0.052(8) Uiso 1 4 d . . .
H7 H -0.344(2) 0.0237(11) -0.158(4) 0.023(6) Uiso 1 4 d . . .
H8 H 0.316(4) -0.120(2) 0.699(6) 0.094(13) Uiso 1 4 d . . .
H9 H 0.202(4) -0.1595(15) 0.709(5) 0.060(9) Uiso 1 4 d . . .
H10 H 0.641(4) 0.2276(19) 0.415(6) 0.079(12) Uiso 1 4 d . . .
H11 H 0.631(4) 0.289(2) 0.522(7) 0.106(15) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.212(3) yes . .
O2 C4 1.216(3) yes . .
N1 N2 1.334(3) yes . .
N1 C2 1.342(3) yes . .
N2 N3 1.327(3) yes . .
N3 C3 1.343(3) yes . .
N4 C5 1.340(3) yes . 3_556
N4 C6 1.336(3) yes . .
C1 C2 1.464(4) yes . .
C1 C6 1.523(4) yes . .
C2 C3 1.398(3) yes . .
C3 C4 1.465(4) yes . .
C4 C5 1.507(4) yes . .
C5 C6 1.401(3) yes . .
C7 C8 1.370(4) yes . .
C7 C15 1.399(4) yes . 3_555
C8 C9 1.425(4) yes . .
C9 C10 1.413(4) yes . .
C9 C16 1.426(4) yes . .
C10 C11 1.369(4) yes . .
C11 C12 1.398(4) yes . .
C12 C13 1.387(4) yes . .
C13 C14 1.476(4) yes . .
C13 C16 1.433(4) yes . .
C14 C15 1.392(4) yes . .
C14 C16 1.431(3) yes . 3_555
O3 H8 0.96(4) no . .
O3 H9 0.89(4) no . .
O4 H10 0.86(4) no . .
O4 H11 0.91(4) no . .
N2 H1C 0.92(4) no . .
C7 H2 1.00(3) no . .
C8 H3 0.97(3) no . .
C10 H4 0.97(3) no . .
C11 H5 0.97(3) no . .
C12 H6 1.00(3) no . .
C15 H7 0.98(2) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 N1 C2 102.4(2) yes . . .
N1 N2 N3 117.2(2) yes . . .
N2 N3 C3 102.4(2) yes . . .
C5 N4 C6 116.8(2) yes 3_556 . .
O1 C1 C2 125.9(2) yes . . .
O1 C1 C6 121.5(2) yes . . .
C2 C1 C6 112.6(2) yes . . .
N1 C2 C1 127.0(2) yes . . .
N1 C2 C3 108.9(2) yes . . .
C1 C2 C3 124.2(2) yes . . .
N3 C3 C2 109.1(2) yes . . .
N3 C3 C4 126.6(2) yes . . .
C2 C3 C4 124.3(2) yes . . .
O2 C4 C3 125.0(2) yes . . .
O2 C4 C5 122.0(2) yes . . .
C3 C4 C5 113.0(2) yes . . .
N4 C5 C4 115.5(2) yes 3_556 . .
N4 C5 C6 121.5(2) yes 3_556 . .
C4 C5 C6 123.0(2) yes . . .
N4 C6 C1 115.5(2) yes . . .
N4 C6 C5 121.7(2) yes . . .
C1 C6 C5 122.8(2) yes . . .
C8 C7 C15 120.8(3) yes . . 3_555
C7 C8 C9 119.9(3) yes . . .
C8 C9 C10 120.4(3) yes . . .
C8 C9 C16 119.7(2) yes . . .
C10 C9 C16 119.9(2) yes . . .
C9 C10 C11 120.2(3) yes . . .
C10 C11 C12 120.6(2) yes . . .
C11 C12 C13 121.6(3) yes . . .
C12 C13 C14 122.3(2) yes . . .
C12 C13 C16 118.8(2) yes . . .
C14 C13 C16 119.0(2) yes . . .
C13 C14 C15 122.1(2) yes . . .
C13 C14 C16 119.2(2) yes . . 3_555
C15 C14 C16 118.7(2) yes . . 3_555
C7 C15 C14 121.7(2) yes 3_555 . .
C9 C16 C13 119.0(2) yes . . .
C9 C16 C14 119.2(2) yes . . 3_555
C13 C16 C14 121.8(2) yes . . 3_555
H8 O3 H9 107(3) no . . .
H10 O4 H11 112(4) no . . .
N1 N2 H1C 122(2) no . . .
N3 N2 H1C 121(2) no . . .
C8 C7 H2 118.6(14) no . . .
C15 C7 H2 120.5(14) no 3_555 . .
C7 C8 H3 121.2(16) no . . .
C9 C8 H3 118.8(16) no . . .
C9 C10 H4 119.7(18) no . . .
C11 C10 H4 120.1(18) no . . .
C10 C11 H5 120.2(19) no . . .
C12 C11 H5 119.1(19) no . . .
C11 C12 H6 119.1(16) no . . .
C13 C12 H6 119.3(16) no . . .
C7 C15 H7 118.0(14) no 3_555 . .
C14 C15 H7 120.3(14) 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 179.3(2) no . . . .
N2 N1 C2 C3 -0.4(3) no . . . .
C2 N1 N2 N3 0.3(3) no . . . .
N1 N2 N3 C3 -0.1(3) no . . . .
N2 N3 C3 C2 -0.1(3) no . . . .
N2 N3 C3 C4 179.4(2) no . . . .
C5 N4 C6 C1 -179.9(2) no 3_556 . . .
C5 N4 C6 C5 -0.2(4) no 3_556 . . .
C6 N4 C5 C4 -180.0(2) no . . 3_556 3_556
C6 N4 C5 C6 0.2(4) no . . 3_556 3_556
O1 C1 C2 N1 -2.8(5) no . . . .
O1 C1 C2 C3 176.8(2) no . . . .
O1 C1 C6 N4 2.5(4) no . . . .
O1 C1 C6 C5 -177.2(2) no . . . .
C2 C1 C6 N4 -177.3(2) no . . . .
C2 C1 C6 C5 3.1(3) no . . . .
C6 C1 C2 N1 176.9(2) no . . . .
C6 C1 C2 C3 -3.5(4) no . . . .
N1 C2 C3 N3 0.3(3) no . . . .
N1 C2 C3 C4 -179.2(2) no . . . .
C1 C2 C3 N3 -179.3(2) no . . . .
C1 C2 C3 C4 1.2(4) no . . . .
N3 C3 C4 O2 1.5(4) no . . . .
N3 C3 C4 C5 -177.6(2) no . . . .
C2 C3 C4 O2 -179.1(2) no . . . .
C2 C3 C4 C5 1.8(4) no . . . .
O2 C4 C5 N4 -1.5(4) no . . . 3_556
O2 C4 C5 C6 178.7(2) no . . . .
C3 C4 C5 N4 177.6(2) no . . . 3_556
C3 C4 C5 C6 -2.1(3) no . . . .
N4 C5 C6 N4 0.3(4) no 3_556 . . .
N4 C5 C6 C1 179.9(2) no 3_556 . . .
C4 C5 C6 N4 -180.0(2) no . . . .
C4 C5 C6 C1 -0.4(4) no . . . .
C8 C7 C15 C14 0.5(4) no . . 3_555 3_555
C15 C7 C8 C9 -0.6(4) no 3_555 . . .
C7 C8 C9 C10 179.8(2) no . . . .
C7 C8 C9 C16 0.4(4) no . . . .
C8 C9 C10 C11 -179.9(2) no . . . .
C8 C9 C16 C13 -180.0(2) no . . . .
C8 C9 C16 C14 -0.1(4) no . . . 3_555
C10 C9 C16 C13 0.7(4) no . . . .
C10 C9 C16 C14 -179.5(2) no . . . 3_555
C16 C9 C10 C11 -0.5(4) no . . . .
C9 C10 C11 C12 -0.1(4) no . . . .
C10 C11 C12 C13 0.5(4) no . . . .
C11 C12 C13 C14 -179.8(2) no . . . .
C11 C12 C13 C16 -0.4(4) no . . . .
C12 C13 C14 C15 -0.8(4) no . . . .
C12 C13 C14 C16 -180.0(2) no . . . 3_555
C12 C13 C16 C9 -0.2(4) no . . . .
C12 C13 C16 C14 179.9(2) no . . . 3_555
C14 C13 C16 C9 179.2(2) no . . . .
C14 C13 C16 C14 -0.7(4) no . . . 3_555
C16 C13 C14 C15 179.8(2) no . . . .
C16 C13 C14 C16 0.6(4) no . . . 3_555
C13 C14 C15 C7 -179.0(2) no . . . 3_555
C13 C14 C16 C9 179.2(2) no . . 3_555 3_555
C13 C14 C16 C13 -0.7(4) no . . 3_555 3_555
C15 C14 C16 C9 -0.0(4) no . . 3_555 3_555
C15 C14 C16 C13 -179.9(2) no . . 3_555 3_555
C16 C14 C15 C7 0.2(4) no 3_555 . . 3_555

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.983(3) no . .
O1 N4 2.737(3) no . .
O2 N3 2.963(3) no . .
O2 N4 2.735(3) no . 3_556
N2 C1 3.523(3) no . .
N2 C4 3.517(3) no . .
N4 N4 2.804(3) no . 3_556
C1 C4 3.046(3) no . .
C2 C5 2.852(4) no . .
C3 C6 2.848(4) no . .
C5 C5 2.676(4) no . 3_556
C6 C6 2.674(4) no . 3_556
C7 C16 2.814(4) no . .
C8 C14 2.832(4) no . 3_555
C9 C12 2.791(4) no . .
C9 C15 2.797(4) no . 3_555
C10 C13 2.824(4) no . .
C11 C16 2.811(4) no . .
C12 C15 2.957(4) no . .
C13 C13 2.908(3) no . 3_555
C14 C14 2.903(4) no . 3_555
C16 C16 2.869(4) no . 3_555
O1 O3 3.006(3) no . .
O1 N1 3.473(3) no . 3_656
O1 C7 3.531(4) no . 1_556
O1 C7 3.275(3) no . 3_656
O1 C15 3.594(3) no . 1_656
O1 C15 3.518(4) no . 3_556
O2 O3 2.838(3) no . 3_556
O2 C9 3.560(4) no . .
O2 C10 3.447(4) no . .
O2 C10 3.460(4) no . 1_556
O2 C10 3.195(3) no . 4_555
O2 C11 3.377(4) no . .
O2 C11 3.386(3) no . 4_555
O2 C12 3.420(3) no . .
O2 C13 3.536(3) no . .
O2 C16 3.600(3) no . .
O3 O1 3.006(3) no . .
O3 O2 2.838(3) no . 3_556
O3 O4 2.768(3) no . 2_646
O3 O4 2.796(3) no . 3_656
O3 N4 3.017(3) no . .
O4 O3 2.768(3) no . 2_656
O4 O3 2.796(3) no . 3_656
O4 O4 3.430(3) no . 4_554
O4 O4 3.430(3) no . 4_555
O4 N2 2.664(3) no . .
O4 N2 3.231(3) no . 4_554
O4 N3 3.463(3) no . .
N1 O1 3.473(3) no . 3_656
N1 C7 3.421(4) no . .
N2 O4 2.664(3) no . .
N2 O4 3.231(3) no . 4_555
N2 C7 3.584(4) no . .
N2 C8 3.560(3) no . .
N3 O4 3.463(3) no . .
N3 C8 3.337(4) no . .
N4 O3 3.017(3) no . .
N4 C12 3.437(4) no . 3_555
N4 C13 3.387(4) no . 3_555
N4 C13 3.467(4) no . 3_556
N4 C14 3.277(3) no . 3_556
N4 C16 3.574(3) no . 3_555
C1 C7 3.300(4) no . 1_556
C1 C8 3.564(4) no . 1_556
C1 C14 3.462(3) no . 3_555
C1 C15 3.354(4) no . 3_555
C1 C15 3.497(4) no . 3_556
C2 C7 3.405(4) no . .
C2 C7 3.485(4) no . 1_556
C2 C8 3.360(4) no . 1_556
C2 C15 3.342(4) no . 3_555
C3 C8 3.430(4) no . .
C3 C8 3.475(4) no . 1_556
C3 C9 3.402(4) no . .
C3 C16 3.577(3) no . .
C4 C9 3.413(4) no . .
C4 C9 3.492(4) no . 1_556
C4 C10 3.393(4) no . 1_556
C4 C13 3.512(3) no . .
C4 C16 3.257(4) no . .
C5 C9 3.344(4) no . 1_556
C5 C13 3.474(3) no . .
C5 C14 3.527(4) no . 3_555
C5 C16 3.431(4) no . .
C5 C16 3.429(4) no . 1_556
C6 C9 3.584(4) no . 1_556
C6 C13 3.302(4) no . 3_555
C6 C14 3.395(4) no . 3_555
C6 C14 3.456(4) no . 3_556
C6 C16 3.440(4) no . 1_556
C7 O1 3.531(4) no . 1_554
C7 O1 3.275(3) no . 3_656
C7 N1 3.421(4) no . .
C7 N2 3.584(4) no . .
C7 C1 3.300(4) no . 1_554
C7 C2 3.485(4) no . 1_554
C7 C2 3.405(4) no . .
C8 N2 3.560(3) no . .
C8 N3 3.337(4) no . .
C8 C1 3.564(4) no . 1_554
C8 C2 3.360(4) no . 1_554
C8 C3 3.475(4) no . 1_554
C8 C3 3.430(4) no . .
C9 O2 3.560(4) no . .
C9 C3 3.402(4) no . .
C9 C4 3.492(4) no . 1_554
C9 C4 3.413(4) no . .
C9 C5 3.344(4) no . 1_554
C9 C6 3.584(4) no . 1_554
C10 O2 3.460(4) no . 1_554
C10 O2 3.447(4) no . .
C10 O2 3.195(3) no . 4_554
C10 C4 3.393(4) no . 1_554
C11 O2 3.377(4) no . .
C11 O2 3.386(3) no . 4_554
C12 O2 3.420(3) no . .
C12 N4 3.437(4) no . 3_555
C13 O2 3.536(3) no . .
C13 N4 3.387(4) no . 3_555
C13 N4 3.467(4) no . 3_556
C13 C4 3.512(3) no . .
C13 C5 3.474(3) no . .
C13 C6 3.302(4) no . 3_555
C14 N4 3.277(3) no . 3_556
C14 C1 3.462(3) no . 3_555
C14 C5 3.527(4) no . 3_555
C14 C6 3.395(4) no . 3_555
C14 C6 3.456(4) no . 3_556
C15 O1 3.594(3) no . 1_454
C15 O1 3.518(4) no . 3_556
C15 C1 3.354(4) no . 3_555
C15 C1 3.497(4) no . 3_556
C15 C2 3.342(4) no . 3_555
C16 O2 3.600(3) no . .
C16 N4 3.574(3) no . 3_555
C16 C3 3.577(3) no . .
C16 C4 3.257(4) no . .
C16 C5 3.429(4) no . 1_554
C16 C5 3.431(4) no . .
C16 C6 3.440(4) no . 1_554
C2 H1C 2.97(4) no . .
C3 H1C 2.96(4) no . .
C8 H4 2.64(3) no . .
C8 H7 3.28(2) no . 3_555
C9 H2 3.32(3) no . .
C9 H5 3.29(3) no . .
C10 H3 2.63(3) no . .
C10 H6 3.29(3) no . .
C12 H4 3.28(3) no . .
C12 H7 2.65(2) no . .
C13 H5 3.29(3) no . .
C13 H7 2.70(2) no . .
C14 H2 3.34(3) no . 3_555
C14 H6 2.69(3) no . .
C15 H3 3.29(3) no . 3_555
C15 H6 2.63(3) no . .
C16 H3 3.33(3) no . .
C16 H4 3.33(3) no . .
C16 H6 3.33(3) no . .
C16 H7 3.32(2) no . 3_555
H2 H3 2.35(4) no . .
H2 H7 2.37(3) no . 3_555
H3 H4 2.45(4) no . .
H4 H5 2.34(4) no . .
H5 H6 2.35(4) no . .
H6 H7 2.03(4) no . .
O1 H2 3.59(3) no . 1_556
O1 H2 2.48(2) no . 3_656
O1 H6 3.41(3) no . 3_555
O1 H7 3.11(2) no . 1_656
O1 H7 3.28(2) no . 3_555
O1 H7 3.57(3) no . 3_556
O1 H8 2.06(4) no . .
O1 H9 3.33(3) no . .
O2 H4 3.40(3) no . 1_556
O2 H4 2.49(3) no . 4_555
O2 H5 2.90(3) no . 4_555
O2 H8 3.33(4) no . 3_556
O2 H9 1.96(4) no . 3_556
O3 H1C 3.47(4) no . 3_656
O3 H2 3.22(3) no . 3_656
O3 H5 3.01(3) no . 2_545
O3 H5 3.30(3) no . 3_555
O3 H6 3.42(3) no . 3_556
O3 H10 3.21(4) no . 2_646
O3 H10 1.97(4) no . 3_656
O3 H11 1.90(4) no . 2_646
O3 H11 3.39(5) no . 3_656
O4 H1C 1.76(4) no . .
O4 H1C 2.92(3) no . 4_554
O4 H3 3.49(3) no . 4_555
O4 H5 3.00(3) no . 1_656
O4 H5 3.41(4) no . 4_655
O4 H6 3.45(3) no . 4_655
O4 H8 3.46(4) no . 2_656
O4 H8 3.21(4) no . 3_656
O4 H9 3.20(3) no . 2_656
O4 H9 3.37(4) no . 3_656
O4 H10 3.14(4) no . 4_555
O4 H11 3.18(5) no . 4_554
N1 H2 3.34(3) no . .
N1 H6 3.05(3) no . 1_656
N1 H7 3.00(2) no . 1_656
N1 H10 3.60(4) no . .
N2 H2 3.54(3) no . .
N2 H3 3.51(3) no . .
N2 H3 3.46(3) no . 4_555
N2 H10 2.93(4) no . .
N2 H11 3.29(5) no . .
N2 H11 3.57(4) no . 4_555
N3 H3 3.34(3) no . .
N3 H3 3.59(3) no . 1_556
N3 H3 2.91(3) no . 4_555
N3 H4 2.80(3) no . 4_555
N4 H8 2.62(4) no . .
N4 H9 2.53(3) no . .
C1 H2 3.56(2) no . 1_556
C1 H7 3.31(3) no . 3_555
C1 H8 2.94(4) no . .
C2 H2 3.60(3) no . 1_556
C2 H3 3.39(3) no . 1_556
C2 H7 3.56(2) no . 3_555
C3 H3 3.35(3) no . 1_556
C3 H4 3.35(3) no . 4_555
C4 H4 3.46(3) no . 1_556
C4 H4 3.23(3) no . 4_555
C4 H9 2.83(4) no . 3_556
C5 H9 3.14(3) no . 3_556
C6 H8 3.25(4) no . .
C7 H8 3.59(4) no . 3_656
C11 H9 3.38(3) no . 3_555
C11 H10 3.35(3) no . 1_454
C12 H8 3.52(4) no . 3_555
C12 H9 3.39(4) no . 3_556
C12 H11 3.50(5) no . 4_454
H1C O3 3.47(4) no . 3_656
H1C O4 1.76(4) no . .
H1C O4 2.92(3) no . 4_555
H1C H3 3.25(5) no . 4_555
H1C H6 3.40(4) no . 1_656
H1C H8 3.40(6) no . 3_656
H1C H10 2.08(6) no . .
H1C H10 3.10(5) no . 4_555
H1C H11 2.38(6) no . .
H1C H11 3.35(6) no . 4_555
H2 O1 3.59(3) no . 1_554
H2 O1 2.48(2) no . 3_656
H2 O3 3.22(3) no . 3_656
H2 N1 3.34(3) no . .
H2 N2 3.54(3) no . .
H2 C1 3.56(2) no . 1_554
H2 C2 3.60(3) no . 1_554
H2 H7 3.49(4) no . 1_655
H2 H8 2.64(4) no . 3_656
H2 H11 3.57(6) no . 4_554
H3 O4 3.49(3) no . 4_554
H3 N2 3.51(3) no . .
H3 N2 3.46(3) no . 4_554
H3 N3 3.59(3) no . 1_554
H3 N3 3.34(3) no . .
H3 N3 2.91(3) no . 4_554
H3 C2 3.39(3) no . 1_554
H3 C3 3.35(3) no . 1_554
H3 H1C 3.25(5) no . 4_554
H3 H11 3.52(6) no . 4_554
H4 O2 3.40(3) no . 1_554
H4 O2 2.49(3) no . 4_554
H4 N3 2.80(3) no . 4_554
H4 C3 3.35(3) no . 4_554
H4 C4 3.46(3) no . 1_554
H4 C4 3.23(3) no . 4_554
H5 O2 2.90(3) no . 4_554
H5 O3 3.01(3) no . 2_555
H5 O3 3.30(3) no . 3_555
H5 O4 3.00(3) no . 1_454
H5 O4 3.41(4) no . 4_454
H5 H8 3.51(5) no . 3_555
H5 H9 2.76(4) no . 2_555
H5 H9 3.21(5) no . 3_555
H5 H10 2.60(4) no . 1_454
H5 H10 2.99(6) no . 4_454
H5 H11 2.80(5) no . 1_454
H5 H11 3.31(7) no . 4_454
H6 O1 3.41(3) no . 3_555
H6 O3 3.42(3) no . 3_556
H6 O4 3.45(3) no . 4_454
H6 N1 3.05(3) no . 1_454
H6 H1C 3.40(4) no . 1_454
H6 H8 3.33(5) no . 3_555
H6 H9 3.31(5) no . 3_556
H6 H10 3.49(5) no . 1_454
H6 H11 2.97(6) no . 4_454
H7 O1 3.11(2) no . 1_454
H7 O1 3.28(2) no . 3_555
H7 O1 3.57(3) no . 3_556
H7 N1 3.00(2) no . 1_454
H7 C1 3.31(3) no . 3_555
H7 C2 3.56(2) no . 3_555
H7 H2 3.49(4) no . 1_455
H8 O1 2.06(4) no . .
H8 O2 3.33(4) no . 3_556
H8 O4 3.46(4) no . 2_646
H8 O4 3.21(4) no . 3_656
H8 N4 2.62(4) no . .
H8 C1 2.94(4) no . .
H8 C6 3.25(4) no . .
H8 C7 3.59(4) no . 3_656
H8 C12 3.52(4) no . 3_555
H8 H1C 3.40(6) no . 3_656
H8 H2 2.64(4) no . 3_656
H8 H5 3.51(5) no . 3_555
H8 H6 3.33(5) no . 3_555
H8 H10 2.44(6) no . 3_656
H8 H11 2.60(6) no . 2_646
H9 O1 3.33(3) no . .
H9 O2 1.96(4) no . 3_556
H9 O4 3.20(3) no . 2_646
H9 O4 3.37(4) no . 3_656
H9 N4 2.53(3) no . .
H9 C4 2.83(4) no . 3_556
H9 C5 3.14(3) no . 3_556
H9 C11 3.38(3) no . 3_555
H9 C12 3.39(4) no . 3_556
H9 H5 2.76(4) no . 2_545
H9 H5 3.21(5) no . 3_555
H9 H6 3.31(5) no . 3_556
H9 H10 3.44(5) no . 2_646
H9 H10 2.52(6) no . 3_656
H9 H11 2.34(5) no . 2_646
H10 O3 3.21(4) no . 2_656
H10 O3 1.97(4) no . 3_656
H10 O4 3.14(4) no . 4_554
H10 N1 3.60(4) no . .
H10 N2 2.93(4) no . .
H10 C11 3.35(3) no . 1_656
H10 H1C 2.08(6) no . .
H10 H1C 3.10(5) no . 4_554
H10 H5 2.60(4) no . 1_656
H10 H5 2.99(6) no . 4_655
H10 H6 3.49(5) no . 1_656
H10 H8 2.44(6) no . 3_656
H10 H9 3.44(5) no . 2_656
H10 H9 2.52(6) no . 3_656
H10 H10 3.54(6) no . 4_554
H10 H10 3.54(6) no . 4_555
H10 H11 2.68(7) no . 4_554
H11 O3 1.90(4) no . 2_656
H11 O3 3.39(5) no . 3_656
H11 O4 3.18(5) no . 4_555
H11 N2 3.29(5) no . .
H11 N2 3.57(4) no . 4_554
H11 C12 3.50(5) no . 4_655
H11 H1C 2.38(6) no . .
H11 H1C 3.35(6) no . 4_554
H11 H2 3.57(6) no . 4_555
H11 H3 3.52(6) no . 4_555
H11 H5 2.80(5) no . 1_656
H11 H5 3.31(7) no . 4_655
H11 H6 2.97(6) no . 4_655
H11 H8 2.60(6) no . 2_656
H11 H9 2.34(5) no . 2_656
H11 H10 2.68(7) no . 4_555

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H8 O1 . . . 3.006(3) 0.96(4) 2.06(4) 173(4) no
O3 H8 N4 . . . 3.017(3) 0.96(4) 2.62(4) 105(3) no
O3 H9 O2 . . 3_556 2.838(3) 0.89(4) 1.96(4) 171(3) no
O3 H9 N4 . . . 3.017(3) 0.89(4) 2.53(3) 115(3) no
O4 H10 O3 . . 3_656 2.796(3) 0.86(4) 1.97(4) 159(3) no
O4 H11 O3 . . 2_656 2.768(3) 0.91(4) 1.90(4) 159(5) no
N2 H1C O4 . . . 2.664(3) 0.92(4) 1.76(4) 167(3) no
N2 H1C N1 . . . 1.334(3) 0.92(4) 1.98(4) 34.7(15) no
N2 H1C N3 . . . 1.327(3) 0.92(4) 1.97(4) 35.6(15) 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_BBTzQ
_database_code_depnum_ccdc_archive 'CCDC 1506329'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C6 H4 N6 Na O4'
_chemical_formula_moiety         'C6 H4 N6 Na O4'
_chemical_formula_weight         247.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
_space_group_IT_number           13
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.6805(2)
_cell_length_b                   3.52584(8)
_cell_length_c                   14.4065(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.8049(13)
_cell_angle_gamma                90.0000
_cell_volume                     470.718(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2787
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      68.10
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             250.00
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.967

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4412
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_theta_max         68.190
_diffrn_reflns_theta_min         4.920
_diffrn_reflns_theta_full        68.190
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             861
_reflns_number_gt                784
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1656
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         861
_refine_ls_number_parameters     90
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1252P)²+0.1605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.81
_refine_diff_density_min         -0.49
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Na Na 0.1353 0.1239
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.75 0.0027(3) 0.25 0.0163(5) Uani 1 2 d . . .
O1 O 0.94030(17) 0.0092(4) 0.17581(12) 0.0193(6) Uani 1 4 d . . .
O2 O 0.62777(19) 0.5028(4) 0.15004(13) 0.0181(5) Uani 1 4 d . . .
N1 N 1.2215(2) -0.2481(6) 0.15044(15) 0.0177(5) Uani 1 4 d . . .
N2 N 1.32099(19) -0.3421(6) 0.10589(13) 0.0195(5) Uani 1 4 d . . .
N3 N 1.26990(19) -0.2750(6) 0.01137(13) 0.0184(5) Uani 1 4 d . . .
C1 C 0.9661(2) 0.0107(6) 0.09794(17) 0.0153(6) Uani 1 4 d . . .
C2 C 1.1037(2) -0.1176(7) 0.08333(16) 0.0171(6) Uani 1 4 d . . .
C3 C 0.8653(2) 0.1338(7) 0.00476(16) 0.0168(6) Uani 1 4 d . . .
H1A H 0.641(3) 0.466(9) 0.098(3) 0.035(10) Uiso 1 4 d . . .
H1B H 0.548(5) 0.541(12) 0.135(3) 0.059(13) Uiso 1 4 d . . .
H2 H 1.248(6) -0.231(15) 0.209(3) 0.10(2) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.218(3) yes . .
N1 N2 1.344(3) yes . .
N1 C2 1.346(3) yes . .
N2 N3 1.329(2) yes . .
N3 C3 1.356(3) yes . 3_755
C1 C2 1.478(3) yes . .
C1 C3 1.478(3) yes . .
C2 C3 1.387(4) yes . 3_755
O2 H1A 0.81(4) no . .
O2 H1B 0.76(5) no . .
N1 H2 0.81(5) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 N1 C2 108.5(2) yes . . .
N1 N2 N3 109.87(17) yes . . .
N2 N3 C3 107.21(19) yes . . 3_755
O1 C1 C2 124.28(19) yes . . .
O1 C1 C3 125.5(2) yes . . .
C2 C1 C3 110.2(2) yes . . .
N1 C2 C1 127.9(2) yes . . .
N1 C2 C3 106.3(2) yes . . 3_755
C1 C2 C3 125.82(18) yes . . 3_755
N3 C3 C1 127.9(2) yes 3_755 . .
N3 C3 C2 108.17(18) yes 3_755 . 3_755
C1 C3 C2 123.9(2) yes . . 3_755
H1A O2 H1B 101(4) no . . .
N2 N1 H2 118(5) no . . .
C2 N1 H2 132(4) 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 178.5(2) no . . . .
N2 N1 C2 C3 -0.2(2) no . . . 3_755
C2 N1 N2 N3 0.0(2) no . . . .
N1 N2 N3 C3 0.2(2) no . . . 3_755
N2 N3 C3 C1 179.18(19) no . . 3_755 3_755
N2 N3 C3 C2 -0.3(2) no . . 3_755 .
O1 C1 C2 N1 -1.2(4) no . . . .
O1 C1 C2 C3 177.30(19) no . . . 3_755
O1 C1 C3 N3 2.1(4) no . . . 3_755
O1 C1 C3 C2 -177.32(18) no . . . 3_755
C2 C1 C3 N3 -178.8(2) no . . . 3_755
C2 C1 C3 C2 1.8(3) no . . . 3_755
C3 C1 C2 N1 179.7(2) no . . . .
C3 C1 C2 C3 -1.8(3) no . . . 3_755
N1 C2 C3 N3 0.3(3) no . . 3_755 .
N1 C2 C3 C1 -179.21(18) no . . 3_755 3_755
C1 C2 C3 N3 -178.5(2) no . . 3_755 .
C1 C2 C3 C1 2.1(4) no . . 3_755 3_755

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 2.991(3) no . .
O1 N3 3.020(2) no . 3_755
C1 C1 3.077(4) no . 3_755
C2 C2 2.774(3) no . 3_755
C3 C3 2.813(3) no . 3_755
Na1 Na1 3.5258(15) no . 1_545
Na1 Na1 3.5258(15) no . 1_565
Na1 O1 2.3822(19) no . .
Na1 O1 2.3822(19) no . 2_655
Na1 O2 2.3653(17) no . 1_545
Na1 O2 2.3660(17) no . .
Na1 O2 2.3653(17) no . 2_645
Na1 O2 2.3660(17) no . 2_655
Na1 C1 3.439(3) no . .
Na1 C1 3.439(3) no . 2_655
O1 Na1 2.3822(19) no . .
O1 O1 3.526(2) no . 1_545
O1 O1 3.526(2) no . 1_565
O1 O2 3.439(2) no . 1_545
O1 O2 3.416(2) no . .
O1 O2 3.297(3) no . 2_645
O1 O2 3.273(3) no . 2_655
O1 N2 3.544(2) no . 2_755
O2 Na1 2.3660(17) no . .
O2 Na1 2.3653(17) no . 1_565
O2 O1 3.416(2) no . .
O2 O1 3.439(2) no . 1_565
O2 O1 3.273(3) no . 2_655
O2 O1 3.297(3) no . 2_665
O2 O2 3.526(2) no . 1_545
O2 O2 3.526(2) no . 1_565
O2 O2 3.155(2) no . 2_655
O2 N2 2.904(3) no . 1_465
O2 N3 3.550(2) no . 1_465
O2 N3 2.892(3) no . 3_755
N1 N1 3.526(3) no . 1_545
N1 N1 3.526(3) no . 1_565
N1 N1 2.760(3) no . 2_755
N1 N2 3.450(3) no . 1_565
N1 C1 3.526(3) no . 1_545
N1 C2 3.316(3) no . 1_545
N2 O1 3.544(2) no . 2_755
N2 O2 2.904(3) no . 1_645
N2 N1 3.450(3) no . 1_545
N2 N2 3.526(3) no . 1_545
N2 N2 3.526(3) no . 1_565
N2 N3 3.540(3) no . 1_545
N2 C2 3.408(3) no . 1_545
N2 C3 3.453(3) no . 3_745
N3 O2 3.550(2) no . 1_645
N3 O2 2.892(3) no . 3_755
N3 N2 3.540(3) no . 1_565
N3 N3 3.526(3) no . 1_545
N3 N3 3.526(3) no . 1_565
N3 C1 3.514(3) no . 3_745
N3 C3 3.280(3) no . 3_745
C1 Na1 3.439(3) no . .
C1 N1 3.526(3) no . 1_565
C1 N3 3.514(3) no . 3_745
C1 C1 3.526(3) no . 1_545
C1 C1 3.526(3) no . 1_565
C1 C2 3.380(3) no . 1_565
C1 C3 3.400(3) no . 1_545
C2 N1 3.316(3) no . 1_565
C2 N2 3.408(3) no . 1_565
C2 C1 3.380(3) no . 1_545
C2 C2 3.526(4) no . 1_545
C2 C2 3.526(4) no . 1_565
C2 C3 3.473(3) no . 1_545
C3 N2 3.453(3) no . 3_745
C3 N3 3.280(3) no . 3_745
C3 C1 3.400(3) no . 1_565
C3 C2 3.473(3) no . 1_565
C3 C3 3.526(3) no . 1_545
C3 C3 3.526(3) no . 1_565
O1 H2 3.00(6) no . .
N3 H2 2.92(5) no . .
C1 H2 2.86(5) no . .
C3 H2 2.97(4) no . 3_755
Na1 H1A 2.85(3) no . 1_545
Na1 H1A 2.69(3) no . .
Na1 H1A 2.85(3) no . 2_645
Na1 H1A 2.69(3) no . 2_655
Na1 H1B 2.72(4) no . 1_545
Na1 H1B 2.88(4) no . .
Na1 H1B 2.72(4) no . 2_645
Na1 H1B 2.88(4) no . 2_655
O1 H1A 3.38(3) no . 1_545
O1 H1A 3.22(3) no . .
O1 H1B 3.16(5) no . 2_645
O1 H1B 3.29(5) no . 2_655
O1 H2 3.12(5) no . 2_755
O2 H1A 3.49(3) no . 1_565
O2 H1B 3.47(4) no . 1_545
N1 H1B 3.31(5) no . 1_645
N1 H2 3.56(5) no . 1_545
N1 H2 1.97(5) no . 2_755
N2 H1A 3.21(3) no . 1_645
N2 H1A 3.09(4) no . 3_755
N2 H1B 2.15(5) no . 1_645
N2 H2 2.96(6) no . 2_755
N3 H1A 3.57(3) no . 1_645
N3 H1A 2.11(4) no . 3_755
N3 H1A 3.48(3) no . 3_765
N3 H1B 2.84(4) no . 1_645
N3 H1B 3.25(5) no . 3_755
C1 H1A 3.53(3) no . .
C1 H2 3.42(5) no . 2_755
C2 H2 2.95(4) no . 2_755
C3 H1A 3.09(4) no . .
H1A Na1 2.69(3) no . .
H1A Na1 2.85(3) no . 1_565
H1A O1 3.22(3) no . .
H1A O1 3.38(3) no . 1_565
H1A O2 3.49(3) no . 1_545
H1A N2 3.21(3) no . 1_465
H1A N2 3.09(4) no . 3_755
H1A N3 3.57(3) no . 1_465
H1A N3 2.11(4) no . 3_755
H1A N3 3.48(3) no . 3_765
H1A C1 3.53(3) no . .
H1A C3 3.09(4) no . .
H1A H1A 3.53(4) no . 1_545
H1A H1A 3.53(4) no . 1_565
H1A H1A 3.32(4) no . 3_665
H1A H1B 3.47(5) no . 1_545
H1A H1B 3.32(5) no . 3_665
H1B Na1 2.88(4) no . .
H1B Na1 2.72(4) no . 1_565
H1B O1 3.29(5) no . 2_655
H1B O1 3.16(5) no . 2_665
H1B O2 3.47(4) no . 1_565
H1B N1 3.31(5) no . 1_465
H1B N2 2.15(5) no . 1_465
H1B N3 2.84(4) no . 1_465
H1B N3 3.25(5) no . 3_755
H1B H1A 3.47(5) no . 1_565
H1B H1A 3.32(5) no . 3_665
H1B H1B 3.53(6) no . 1_545
H1B H1B 3.53(6) no . 1_565
H1B H2 3.47(8) no . 1_465
H2 O1 3.12(5) no . 2_755
H2 N1 3.56(5) no . 1_565
H2 N1 1.97(5) no . 2_755
H2 N2 2.96(6) no . 2_755
H2 C1 3.42(5) no . 2_755
H2 C2 2.95(4) no . 2_755
H2 H1B 3.47(8) no . 1_645
H2 H2 3.53(8) no . 1_545
H2 H2 3.53(8) no . 1_565
H2 H2 1.18(7) no . 2_755

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H1A N3 . . 3_755 2.892(3) 0.81(4) 2.11(4) 162(3) no
O2 H1B N2 . . 1_465 2.904(3) 0.76(5) 2.15(5) 174(5) no
N1 H2 N1 . . 2_755 2.760(3) 0.81(5) 1.97(5) 169(6) no
N1 H2 N2 . . . 1.344(3) 0.81(5) 1.86(6) 40(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_BTABQ-Benz1
_database_code_depnum_ccdc_archive 'CCDC 1506330'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C6 H2 N6 O2'
_chemical_formula_moiety         'C6 H2 N6 O2'
_chemical_formula_weight         190.12
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_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
#------------------------------------------------------------------------------
_cell_length_a                   6.46087(12)
_cell_length_b                   5.62884(12)
_cell_length_c                   9.37402(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.3001(9)
_cell_angle_gamma                90.0000
_cell_volume                     336.426(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2381
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      68.21
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192.00
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            3334
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         6.945
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             618
_reflns_number_gt                570
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1079
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         618
_refine_ls_number_parameters     68
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0675P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.12304(17) 0.8163(2) 1.22351(12) 0.0218(4) Uani 1 4 d . . .
N1 N 0.7116(2) 0.8506(3) 1.01823(14) 0.0206(4) Uani 1 4 d . . .
N2 N 0.5713(2) 0.7744(3) 0.90834(15) 0.0222(4) Uani 1 4 d . . .
N3 N 0.6187(2) 0.5815(3) 0.83972(15) 0.0213(4) Uani 1 4 d . . .
C1 C 1.0663(3) 0.6802(3) 1.12432(17) 0.0179(4) Uani 1 4 d . . .
C2 C 0.8653(3) 0.6895(3) 1.02280(17) 0.0175(4) Uani 1 4 d . . .
C3 C 0.8076(3) 0.5240(3) 0.91185(16) 0.0180(4) Uani 1 4 d . . .
H2 H 0.449(5) 0.862(5) 0.879(3) 0.051(7) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXD97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.2149(19) yes . .
N1 N2 1.3286(19) yes . .
N1 C2 1.341(2) yes . .
N2 N3 1.323(2) yes . .
N3 C3 1.336(2) yes . .
C1 C2 1.481(2) yes . .
C1 C3 1.479(2) yes . 3_767
C2 C3 1.401(2) yes . .
N2 H2 0.93(3) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N2 N1 C2 102.45(13) yes . . .
N1 N2 N3 117.34(14) yes . . .
N2 N3 C3 102.54(13) yes . . .
O1 C1 C2 126.46(15) yes . . .
O1 C1 C3 123.77(14) yes . . 3_767
C2 C1 C3 109.77(13) yes . . 3_767
N1 C2 C1 127.76(14) yes . . .
N1 C2 C3 108.60(13) yes . . .
C1 C2 C3 123.64(15) yes . . .
N3 C3 C1 124.35(14) yes . . 3_767
N3 C3 C2 109.06(15) yes . . .
C1 C3 C2 126.58(14) yes 3_767 . .
N1 N2 H2 119.9(16) no . . .
N3 N2 H2 122.7(16) 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 -179.92(14) no . . . .
N2 N1 C2 C3 0.63(17) no . . . .
C2 N1 N2 N3 -0.72(18) no . . . .
N1 N2 N3 C3 0.48(18) no . . . .
N2 N3 C3 C1 -178.82(14) no . . . 3_767
N2 N3 C3 C2 -0.03(17) no . . . .
O1 C1 C2 N1 1.8(3) no . . . .
O1 C1 C2 C3 -178.83(15) no . . . .
O1 C1 C3 N3 0.2(3) no . . 3_767 3_767
O1 C1 C3 C2 178.80(14) no . . 3_767 3_767
C2 C1 C3 N3 -179.57(14) no . . 3_767 3_767
C2 C1 C3 C2 -1.0(2) no . . 3_767 3_767
C3 C1 C2 N1 -178.43(14) no 3_767 . . .
C3 C1 C2 C3 1.0(2) no 3_767 . . .
N1 C2 C3 N3 -0.40(19) no . . . .
N1 C2 C3 C1 178.36(14) no . . . 3_767
C1 C2 C3 N3 -179.88(14) no . . . .
C1 C2 C3 C1 -1.1(3) no . . . 3_767

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N1 3.0254(16) no . .
O1 N3 2.9098(19) no . 3_767
N2 C1 3.538(2) no . .
N2 C1 3.515(2) no . 3_767
C1 C1 3.104(2) no . 3_767
C2 C2 2.828(2) no . 3_767
C3 C3 2.767(2) no . 3_767
O1 O1 3.3092(17) no . 2_747
O1 O1 3.3092(17) no . 2_757
O1 N1 3.2520(19) no . 3_777
O1 N2 3.395(2) no . 3_777
O1 N2 3.1667(17) no . 4_665
O1 N3 3.2629(17) no . 4_665
O1 C1 2.879(2) no . 2_757
O1 C2 3.165(2) no . 2_757
O1 C2 3.486(2) no . 4_565
O1 C3 3.5715(19) no . 2_757
O1 C3 3.040(2) no . 4_565
N1 O1 3.2520(19) no . 3_777
N1 N1 3.181(2) no . 3_677
N1 N2 2.946(2) no . 3_677
N1 N3 3.190(2) no . 4_565
N1 C1 3.383(2) no . 3_777
N2 O1 3.395(2) no . 3_777
N2 O1 3.1667(17) no . 4_464
N2 N1 2.946(2) no . 3_677
N2 N2 3.281(2) no . 3_677
N2 N3 2.997(2) no . 2_656
N2 N3 3.469(2) no . 3_667
N3 O1 3.2629(17) no . 4_464
N3 N1 3.190(2) no . 4_564
N3 N2 2.997(2) no . 2_646
N3 N2 3.469(2) no . 3_667
N3 N3 3.503(2) no . 2_646
N3 N3 3.503(2) no . 2_656
C1 O1 2.879(2) no . 2_747
C1 N1 3.383(2) no . 3_777
C2 O1 3.165(2) no . 2_747
C2 O1 3.486(2) no . 4_564
C3 O1 3.5715(19) no . 2_747
C3 O1 3.040(2) no . 4_564
C2 H2 2.97(3) no . .
C3 H2 2.97(3) no . .
O1 H2 3.57(3) no . 3_777
O1 H2 2.56(3) no . 4_665
N1 H2 2.23(3) no . 3_677
N2 H2 3.54(3) no . 2_646
N2 H2 2.88(3) no . 3_677
N3 H2 2.37(3) no . 2_646
C1 H2 3.16(3) no . 4_665
C2 H2 3.46(3) no . 3_677
C3 H2 3.09(3) no . 2_646
C3 H2 3.52(3) no . 3_667
H2 O1 3.57(3) no . 3_777
H2 O1 2.56(3) no . 4_464
H2 N1 2.23(3) no . 3_677
H2 N2 3.54(3) no . 2_656
H2 N2 2.88(3) no . 3_677
H2 N3 2.37(3) no . 2_656
H2 C1 3.16(3) no . 4_464
H2 C2 3.46(3) no . 3_677
H2 C3 3.09(3) no . 2_656
H2 C3 3.52(3) no . 3_667
H2 H2 2.74(4) no . 3_677

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 N1 . . . 1.3286(19) 0.93(3) 1.97(3) 35.8(11) no
N2 H2 N1 . . 3_677 2.946(2) 0.93(3) 2.23(3) 133(2) no
N2 H2 N3 . . . 1.323(2) 0.93(3) 1.99(3) 34.0(11) no
N2 H2 N3 . . 2_656 2.997(2) 0.93(3) 2.37(3) 124(2) 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_BTABQ-cor1
_database_code_depnum_ccdc_archive 'CCDC 1506331'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C36 H12 N8 O8'
_chemical_formula_moiety         'C36 H12 N8 O8'
_chemical_formula_weight         684.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_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
#------------------------------------------------------------------------------
_cell_length_a                   10.0971
_cell_length_b                   19.4344
_cell_length_c                   7.5505
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.6290
_cell_angle_gamma                90.0000
_cell_volume                     1481.5505
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10813
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_T_max  0.981

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15693
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         4.379
_diffrn_reflns_theta_full        68.210
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2658
_reflns_number_gt                2317
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1557
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     259
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0919P)²+1.0414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O19 O 0.66765(14) 0.52049(7) 0.17654(19) 0.0256(4) Uani 1 4 d . . .
O20 O 0.94948(14) 0.33500(7) -0.2155(2) 0.0256(4) Uani 1 4 d . . .
O25 O 0.76935(15) 0.66250(8) 0.2728(2) 0.0306(4) Uani 1 4 d . . .
O26 O 0.34917(16) 0.24556(8) 0.9674(2) 0.0358(4) Uani 1 4 d . . .
N21 N 0.55690(17) 0.38563(9) 0.0601(2) 0.0257(4) Uani 1 4 d . . .
N22 N 0.56241(17) 0.32428(9) -0.0176(2) 0.0263(4) Uani 1 4 d . . .
N23 N 0.67538(17) 0.30807(9) -0.0965(2) 0.0250(4) Uani 1 4 d . . .
N24 N 1.07184(16) 0.45222(8) -0.0990(2) 0.0211(4) Uani 1 4 d . . .
C1 C 0.7226(2) 0.37329(11) 0.4512(3) 0.0272(5) Uani 1 4 d . . .
C2 C 0.8578(2) 0.37959(10) 0.4016(3) 0.0232(5) Uani 1 4 d . . .
C3 C 0.9244(2) 0.32738(11) 0.3035(3) 0.0272(5) Uani 1 4 d . . .
C4 C 1.0536(2) 0.33471(11) 0.2581(3) 0.0265(5) Uani 1 4 d . . .
C5 C 0.9287(2) 0.43958(10) 0.4501(3) 0.0222(4) Uani 1 4 d . . .
C6 C 1.06433(19) 0.44678(10) 0.4042(3) 0.0217(4) Uani 1 4 d . . .
C7 C 1.1286(2) 0.39429(10) 0.3064(3) 0.0240(5) Uani 1 4 d . . .
C8 C 1.2626(2) 0.40364(11) 0.2593(3) 0.0269(5) Uani 1 4 d . . .
C9 C 1.13589(19) 0.50722(10) 0.4534(3) 0.0212(4) Uani 1 4 d . . .
C10 C 1.3318(2) 0.46157(11) 0.3073(3) 0.0264(5) Uani 1 4 d . . .
C11 C 1.2703(2) 0.51469(11) 0.4064(3) 0.0243(5) Uani 1 4 d . . .
C12 C 1.3392(2) 0.57578(11) 0.4571(3) 0.0270(5) Uani 1 4 d . . .
C13 C 0.72941(19) 0.47825(10) 0.0923(3) 0.0215(4) Uani 1 4 d . . .
C14 C 0.67732(19) 0.41178(10) 0.0302(3) 0.0221(4) Uani 1 4 d . . .
C15 C 0.7502(2) 0.36387(10) -0.0667(3) 0.0222(4) Uani 1 4 d . . .
C16 C 0.88681(19) 0.37460(10) -0.1235(3) 0.0218(4) Uani 1 4 d . . .
C17 C 0.94594(19) 0.44133(10) -0.0578(3) 0.0202(4) Uani 1 4 d . . .
C18 C 1.12707(19) 0.51050(10) -0.0426(3) 0.0203(4) Uani 1 4 d . . .
H8 H 1.313(3) 0.3672(14) 0.186(4) 0.037(7) Uiso 1 4 d . . .
H4 H 1.098(3) 0.2986(14) 0.190(4) 0.033(6) Uiso 1 4 d . . .
H3 H 0.871(2) 0.2869(13) 0.272(3) 0.029(6) Uiso 1 4 d . . .
H1B H 0.677(3) 0.3331(14) 0.423(3) 0.031(6) Uiso 1 4 d . . .
H12B H 1.430(3) 0.5800(12) 0.419(3) 0.028(6) Uiso 1 4 d . . .
H10 H 1.425(3) 0.4682(12) 0.274(3) 0.027(6) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXD97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O19 C13 1.215(2) yes . .
O20 C16 1.218(2) yes . .
N21 N22 1.330(2) yes . .
N21 C14 1.339(3) yes . .
N22 N23 1.330(2) yes . .
N23 C15 1.339(3) yes . .
N24 C17 1.329(3) yes . .
N24 C18 1.330(2) yes . .
C1 C2 1.425(3) yes . .
C1 C12 1.363(3) yes . 3_766
C2 C3 1.429(3) yes . .
C2 C5 1.414(3) yes . .
C3 C4 1.360(3) yes . .
C4 C7 1.429(3) yes . .
C5 C6 1.423(3) yes . .
C5 C9 1.427(3) yes . 3_766
C6 C7 1.420(3) yes . .
C6 C9 1.426(3) yes . .
C7 C8 1.414(3) yes . .
C8 C10 1.372(3) yes . .
C9 C11 1.414(3) yes . .
C10 C11 1.422(3) yes . .
C11 C12 1.426(3) yes . .
C13 C14 1.470(3) yes . .
C13 C18 1.517(3) yes . 3_765
C14 C15 1.398(3) yes . .
C15 C16 1.464(3) yes . .
C16 C17 1.509(3) yes . .
C17 C18 1.417(3) yes . 3_765
C1 H1B 0.93(3) no . .
C3 H3 0.98(3) no . .
C4 H4 0.98(3) no . .
C8 H8 1.03(3) no . .
C10 H10 0.98(3) no . .
C12 H12B 0.97(3) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N22 N21 C14 102.90(16) yes . . .
N21 N22 N23 116.73(17) yes . . .
N22 N23 C15 102.58(16) yes . . .
C17 N24 C18 117.35(17) yes . . .
C2 C1 C12 121.1(2) yes . . 3_766
C1 C2 C3 122.21(19) yes . . .
C1 C2 C5 119.10(18) yes . . .
C3 C2 C5 118.69(18) yes . . .
C2 C3 C4 121.0(2) yes . . .
C3 C4 C7 121.9(2) yes . . .
C2 C5 C6 120.23(18) yes . . .
C2 C5 C9 119.79(18) yes . . 3_766
C6 C5 C9 119.98(18) yes . . 3_766
C5 C6 C7 120.16(18) yes . . .
C5 C6 C9 120.24(18) yes . . .
C7 C6 C9 119.59(18) yes . . .
C4 C7 C6 118.09(18) yes . . .
C4 C7 C8 123.07(19) yes . . .
C6 C7 C8 118.83(18) yes . . .
C7 C8 C10 121.66(19) yes . . .
C5 C9 C6 119.79(17) yes 3_766 . .
C5 C9 C11 119.94(18) yes 3_766 . .
C6 C9 C11 120.28(18) yes . . .
C8 C10 C11 120.73(19) yes . . .
C9 C11 C10 118.90(19) yes . . .
C9 C11 C12 119.01(19) yes . . .
C10 C11 C12 122.09(19) yes . . .
C1 C12 C11 121.0(2) yes 3_766 . .
O19 C13 C14 125.24(18) yes . . .
O19 C13 C18 121.96(17) yes . . 3_765
C14 C13 C18 112.79(16) yes . . 3_765
N21 C14 C13 127.02(18) yes . . .
N21 C14 C15 108.62(17) yes . . .
C13 C14 C15 124.32(18) yes . . .
N23 C15 C14 109.16(18) yes . . .
N23 C15 C16 126.69(18) yes . . .
C14 C15 C16 124.15(18) yes . . .
O20 C16 C15 125.03(18) yes . . .
O20 C16 C17 121.61(17) yes . . .
C15 C16 C17 113.36(16) yes . . .
N24 C17 C16 115.84(17) yes . . .
N24 C17 C18 121.64(18) yes . . 3_765
C16 C17 C18 122.51(17) yes . . 3_765
N24 C18 C13 116.23(17) yes . . 3_765
N24 C18 C17 121.00(17) yes . . 3_765
C13 C18 C17 122.77(17) yes 3_765 . 3_765
C2 C1 H1B 118.9(16) no . . .
C12 C1 H1B 119.9(16) no 3_766 . .
C2 C3 H3 115.9(15) no . . .
C4 C3 H3 123.2(15) no . . .
C3 C4 H4 120.0(15) no . . .
C7 C4 H4 118.2(15) no . . .
C7 C8 H8 121.7(15) no . . .
C10 C8 H8 116.7(15) no . . .
C8 C10 H10 121.8(14) no . . .
C11 C10 H10 117.5(14) no . . .
C1 C12 H12B 122.0(14) no 3_766 . .
C11 C12 H12B 116.9(14) 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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N22 N21 C14 C13 -177.57(17) no . . . .
N22 N21 C14 C15 0.3(2) no . . . .
C14 N21 N22 N23 -0.3(2) no . . . .
N21 N22 N23 C15 0.2(2) no . . . .
N22 N23 C15 C14 -0.0(2) no . . . .
N22 N23 C15 C16 179.66(17) no . . . .
C17 N24 C18 C13 -179.69(15) no . . . 3_765
C17 N24 C18 C17 0.2(3) no . . . 3_765
C18 N24 C17 C16 -179.83(15) no . . . .
C18 N24 C17 C18 -0.2(3) no . . . 3_765
C2 C1 C12 C11 -0.5(3) no . . 3_766 3_766
C12 C1 C2 C3 -179.15(18) no 3_766 . . .
C12 C1 C2 C5 0.6(3) no 3_766 . . .
C1 C2 C3 C4 -179.90(18) no . . . .
C1 C2 C5 C6 179.19(16) no . . . .
C1 C2 C5 C9 -0.3(3) no . . . 3_766
C3 C2 C5 C6 -1.1(3) no . . . .
C3 C2 C5 C9 179.39(16) no . . . 3_766
C5 C2 C3 C4 0.4(3) no . . . .
C2 C3 C4 C7 0.2(3) no . . . .
C3 C4 C7 C6 -0.1(3) no . . . .
C3 C4 C7 C8 -179.26(18) no . . . .
C2 C5 C6 C7 1.2(3) no . . . .
C2 C5 C6 C9 -179.89(16) no . . . .
C2 C5 C9 C6 179.89(16) no . . 3_766 3_766
C2 C5 C9 C11 0.1(3) no . . 3_766 3_766
C6 C5 C9 C6 0.4(3) no . . 3_766 3_766
C6 C5 C9 C11 -179.44(16) no . . 3_766 3_766
C9 C5 C6 C7 -179.30(16) no 3_766 . . .
C9 C5 C6 C9 -0.4(3) no 3_766 . . .
C5 C6 C7 C4 -0.6(3) no . . . .
C5 C6 C7 C8 178.59(16) no . . . .
C5 C6 C9 C5 0.4(3) no . . . 3_766
C5 C6 C9 C11 -179.44(16) no . . . .
C7 C6 C9 C5 179.30(16) no . . . 3_766
C7 C6 C9 C11 -0.5(3) no . . . .
C9 C6 C7 C4 -179.50(16) no . . . .
C9 C6 C7 C8 -0.3(3) no . . . .
C4 C7 C8 C10 179.82(18) no . . . .
C6 C7 C8 C10 0.7(3) no . . . .
C7 C8 C10 C11 -0.2(3) no . . . .
C5 C9 C11 C10 -178.81(16) no 3_766 . . .
C5 C9 C11 C12 0.0(3) no 3_766 . . .
C6 C9 C11 C10 1.0(3) no . . . .
C6 C9 C11 C12 179.85(16) no . . . .
C8 C10 C11 C9 -0.6(3) no . . . .
C8 C10 C11 C12 -179.46(18) no . . . .
C9 C11 C12 C1 -0.3(3) no . . . 3_766
C10 C11 C12 C1 178.54(18) no . . . 3_766
O19 C13 C14 N21 -2.5(3) no . . . .
O19 C13 C14 C15 -180.00(17) no . . . .
O19 C13 C18 N24 1.1(3) no . . 3_765 3_765
O19 C13 C18 C17 -179.02(16) no . . 3_765 .
C14 C13 C18 N24 -178.09(15) no . . 3_765 3_765
C14 C13 C18 C17 1.8(3) no . . 3_765 .
C18 C13 C14 N21 176.65(16) no 3_765 . . .
C18 C13 C14 C15 -0.9(3) no 3_765 . . .
N21 C14 C15 N23 -0.2(2) no . . . .
N21 C14 C15 C16 -179.85(16) no . . . .
C13 C14 C15 N23 177.76(17) no . . . .
C13 C14 C15 C16 -1.9(3) no . . . .
N23 C15 C16 O20 4.3(3) no . . . .
N23 C15 C16 C17 -176.11(17) no . . . .
C14 C15 C16 O20 -176.08(18) no . . . .
C14 C15 C16 C17 3.5(3) no . . . .
O20 C16 C17 N24 -3.3(3) no . . . .
O20 C16 C17 C18 177.13(16) no . . . 3_765
C15 C16 C17 N24 177.10(15) no . . . .
C15 C16 C17 C18 -2.5(3) no . . . 3_765
N24 C17 C18 N24 0.2(3) no . . 3_765 3_765
N24 C17 C18 C13 -179.68(16) no . . 3_765 .
C16 C17 C18 N24 179.81(16) no . . 3_765 3_765
C16 C17 C18 C13 -0.1(3) no . . 3_765 .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O19 N21 2.979(2) no . .
O19 N24 2.753(2) no . 3_765
O20 N23 2.966(2) no . .
O20 N24 2.733(2) no . .
N22 C13 3.529(3) no . .
N22 C16 3.519(3) no . .
N24 N24 2.799(2) no . 3_765
C1 C9 2.816(3) no . 3_766
C2 C7 2.849(3) no . .
C2 C11 2.835(3) no . 3_766
C3 C6 2.817(3) no . .
C4 C5 2.809(3) no . .
C5 C5 2.852(3) no . 3_766
C5 C12 2.818(3) no . 3_766
C6 C6 2.847(3) no . 3_766
C6 C10 2.820(3) no . .
C7 C11 2.841(3) no . .
C8 C9 2.807(3) no . .
C9 C9 2.854(3) no . 3_766
C13 C16 3.049(3) no . .
C14 C17 2.858(3) no . .
C15 C18 2.856(3) no . 3_765
C17 C17 2.671(3) no . 3_765
C18 C18 2.684(3) no . 3_765
O19 O25 3.030(2) no . .
O19 N21 3.402(2) no . 3_665
O19 C1 3.573(3) no . .
O19 C9 3.451(2) no . 3_766
O19 C11 3.276(2) no . 3_766
O19 C12 3.341(3) no . 3_766
O20 O25 2.877(2) no . 3_765
O20 C1 3.465(3) no . 1_554
O20 C2 3.147(3) no . 1_554
O20 C3 3.169(3) no . 4_554
O20 C4 3.468(3) no . 4_554
O20 C5 3.246(2) no . 1_554
O25 O19 3.030(2) no . .
O25 O20 2.877(2) no . 3_765
O25 O26 2.817(2) no . 2_656
O25 O26 2.805(2) no . 3_666
O25 N24 3.052(2) no . 3_765
O25 C7 3.507(3) no . 3_766
O26 O25 2.817(2) no . 2_646
O26 O25 2.805(2) no . 3_666
O26 N21 3.502(2) no . 1_556
O26 N22 2.643(2) no . 1_556
O26 N23 3.549(2) no . 1_556
O26 C8 3.407(3) no . 4_455
N21 O19 3.402(2) no . 3_665
N21 O26 3.502(2) no . 1_554
N21 C1 3.387(3) no . .
N21 C8 3.364(3) no . 1_455
N21 C10 3.305(3) no . 1_455
N22 O26 2.643(2) no . 1_554
N23 O26 3.549(2) no . 1_554
N23 C1 3.574(3) no . 4_554
N23 C12 3.539(3) no . 3_765
N24 O25 3.052(2) no . 3_765
N24 C4 3.539(3) no . .
N24 C5 3.384(3) no . 3_765
N24 C6 3.314(3) no . 3_765
N24 C7 3.305(3) no . .
N24 C8 3.436(3) no . .
N24 C9 3.472(3) no . 3_765
C1 O19 3.573(3) no . .
C1 O20 3.465(3) no . 1_556
C1 N21 3.387(3) no . .
C1 N23 3.574(3) no . 4_555
C1 C13 3.393(3) no . .
C1 C14 3.293(3) no . .
C1 C16 3.597(3) no . 1_556
C2 O20 3.147(3) no . 1_556
C2 C13 3.278(3) no . .
C2 C14 3.386(3) no . .
C2 C16 3.595(3) no . 1_556
C2 C18 3.456(3) no . 3_765
C3 O20 3.169(3) no . 4_555
C3 C15 3.362(3) no . .
C3 C16 3.370(3) no . .
C3 C17 3.522(3) no . .
C4 O20 3.468(3) no . 4_555
C4 N24 3.539(3) no . .
C4 C16 3.411(3) no . .
C4 C17 3.333(3) no . .
C5 O20 3.246(2) no . 1_556
C5 N24 3.384(3) no . 3_765
C5 C13 3.434(3) no . .
C5 C16 3.488(3) no . 1_556
C5 C18 3.269(3) no . 3_765
C6 N24 3.314(3) no . 3_765
C6 C17 3.402(3) no . 3_765
C6 C18 3.429(3) no . 3_765
C7 O25 3.507(3) no . 3_766
C7 N24 3.305(3) no . .
C7 C17 3.419(3) no . .
C7 C18 3.470(3) no . .
C8 O26 3.407(3) no . 4_654
C8 N21 3.364(3) no . 1_655
C8 N24 3.436(3) no . .
C8 C13 3.511(3) no . 3_765
C8 C18 3.363(3) no . .
C9 O19 3.451(2) no . 3_766
C9 N24 3.472(3) no . 3_765
C9 C16 3.394(3) no . 3_765
C9 C17 3.248(3) no . 3_765
C10 N21 3.305(3) no . 1_655
C10 C13 3.288(3) no . 3_765
C10 C14 3.543(3) no . 3_765
C10 C18 3.469(3) no . .
C11 O19 3.276(2) no . 3_766
C11 C15 3.490(3) no . 3_765
C11 C16 3.411(3) no . 3_765
C11 C17 3.507(3) no . 3_765
C12 O19 3.341(3) no . 3_766
C12 N23 3.539(3) no . 3_765
C12 C15 3.289(3) no . 3_765
C12 C16 3.515(3) no . 3_765
C13 C1 3.393(3) no . .
C13 C2 3.278(3) no . .
C13 C5 3.434(3) no . .
C13 C8 3.511(3) no . 3_765
C13 C10 3.288(3) no . 3_765
C14 C1 3.293(3) no . .
C14 C2 3.386(3) no . .
C14 C10 3.543(3) no . 3_765
C15 C3 3.362(3) no . .
C15 C11 3.490(3) no . 3_765
C15 C12 3.289(3) no . 3_765
C16 C1 3.597(3) no . 1_554
C16 C2 3.595(3) no . 1_554
C16 C3 3.370(3) no . .
C16 C4 3.411(3) no . .
C16 C5 3.488(3) no . 1_554
C16 C9 3.394(3) no . 3_765
C16 C11 3.411(3) no . 3_765
C16 C12 3.515(3) no . 3_765
C17 C3 3.522(3) no . .
C17 C4 3.333(3) no . .
C17 C6 3.402(3) no . 3_765
C17 C7 3.419(3) no . .
C17 C9 3.248(3) no . 3_765
C17 C11 3.507(3) no . 3_765
C18 C2 3.456(3) no . 3_765
C18 C5 3.269(3) no . 3_765
C18 C6 3.429(3) no . 3_765
C18 C7 3.470(3) no . .
C18 C8 3.363(3) no . .
C18 C10 3.469(3) no . .
C1 H3 2.64(3) no . .
C2 H4 3.32(3) no . .
C2 H12B 3.31(3) no . 3_766
C3 H1B 2.66(3) no . .
C4 H8 2.76(3) no . .
C5 H3 3.31(3) no . .
C5 H1B 3.28(3) no . .
C6 H8 3.39(3) no . .
C6 H4 3.32(3) no . .
C7 H3 3.34(3) no . .
C7 H10 3.33(3) no . .
C8 H4 2.68(3) no . .
C9 H12B 3.30(3) no . .
C9 H10 3.32(3) no . .
C10 H12B 2.64(2) no . .
C11 H8 3.34(3) no . .
C11 H1B 3.27(3) no . 3_766
C12 H10 2.65(2) no . .
H8 H4 2.55(4) no . .
H8 H10 2.36(4) no . .
H4 H3 2.39(4) no . .
H3 H1B 2.45(4) no . .
H1B H12B 2.34(4) no . 3_766
H12B H10 2.43(3) no . .
O19 H8 3.51(3) no . 3_765
O19 H12B 3.25(3) no . 1_455
O19 H10 2.76(3) no . 1_455
O19 H10 3.53(2) no . 3_765
O20 H4 3.46(3) no . .
O20 H4 3.09(3) no . 4_554
O20 H3 2.50(3) no . 4_554
O25 H4 2.98(3) no . 2_755
O26 H8 2.91(3) no . 1_456
O26 H8 3.07(3) no . 4_455
O26 H4 3.23(3) no . 1_456
O26 H4 3.39(3) no . 4_455
N21 H8 2.67(3) no . 1_455
N21 H1B 3.16(3) no . .
N21 H10 2.65(2) no . 1_455
N22 H8 3.08(3) no . 1_455
N22 H1B 3.52(3) no . .
N22 H1B 3.30(3) no . 4_554
N22 H12B 3.56(2) no . 3_765
N23 H3 3.42(2) no . .
N23 H3 2.89(3) no . 4_554
N23 H1B 2.75(3) no . 4_554
N23 H12B 3.42(2) no . 3_765
C10 H12B 3.26(3) no . 3_866
C12 H10 3.23(2) no . 3_866
C13 H10 3.39(3) no . 1_455
C13 H10 3.33(2) no . 3_765
C14 H1B 3.34(3) no . .
C14 H12B 3.55(2) no . 3_765
C14 H10 3.35(2) no . 1_455
C14 H10 3.43(2) no . 3_765
C15 H3 3.19(3) no . .
C15 H3 3.41(3) no . 4_554
C15 H12B 3.39(2) no . 3_765
C16 H4 3.49(3) no . .
C16 H3 3.44(3) no . .
C16 H3 3.24(3) no . 4_554
H8 O19 3.51(3) no . 3_765
H8 O26 2.91(3) no . 1_654
H8 O26 3.07(3) no . 4_654
H8 N21 2.67(3) no . 1_655
H8 N22 3.08(3) no . 1_655
H4 O20 3.46(3) no . .
H4 O20 3.09(3) no . 4_555
H4 O25 2.98(3) no . 2_745
H4 O26 3.23(3) no . 1_654
H4 O26 3.39(3) no . 4_654
H4 C16 3.49(3) no . .
H3 O20 2.50(3) no . 4_555
H3 N23 3.42(2) no . .
H3 N23 2.89(3) no . 4_555
H3 C15 3.19(3) no . .
H3 C15 3.41(3) no . 4_555
H3 C16 3.44(3) no . .
H3 C16 3.24(3) no . 4_555
H1B N21 3.16(3) no . .
H1B N22 3.52(3) no . .
H1B N22 3.30(3) no . 4_555
H1B N23 2.75(3) no . 4_555
H1B C14 3.34(3) no . .
H12B O19 3.25(3) no . 1_655
H12B N22 3.56(2) no . 3_765
H12B N23 3.42(2) no . 3_765
H12B C10 3.26(3) no . 3_866
H12B C14 3.55(2) no . 3_765
H12B C15 3.39(2) no . 3_765
H12B H10 2.88(3) no . 3_866
H10 O19 2.76(3) no . 1_655
H10 O19 3.53(2) no . 3_765
H10 N21 2.65(2) no . 1_655
H10 C12 3.23(2) no . 3_866
H10 C13 3.39(3) no . 1_655
H10 C13 3.33(2) no . 3_765
H10 C14 3.35(2) no . 1_655
H10 C14 3.43(2) no . 3_765
H10 H12B 2.88(3) no . 3_866
