# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1864642'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N8 O2'
_chemical_formula_sum            'C6 H6 N8 O2'
_chemical_formula_weight         222.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0308(12)
_cell_length_b                   7.8229(10)
_cell_length_c                   12.8172(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     805.23(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    174(2)
_cell_measurement_reflns_used    672
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      25.34

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6386
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      174(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3355
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             738
_reflns_number_gt                490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.5561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         738
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5607(3) 0.1955(3) 0.29710(18) 0.0218(6) Uani 1 1 d . . . . .
H1 H 0.5405 0.0904 0.3397 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7676(4) 0.2811(3) 0.1740(2) 0.0262(7) Uani 1 1 d . . . . .
C3 C 0.6402(4) 0.3536(3) 0.1095(2) 0.0267(7) Uani 1 1 d . . . . .
N1 N 0.5236(3) 0.3471(3) 0.36163(16) 0.0276(6) Uani 1 1 d . . . . .
H1A H 0.593(4) 0.373(4) 0.411(2) 0.033 Uiso 1 1 d . U . . .
N2 N 0.7299(3) 0.1951(3) 0.26236(19) 0.0309(6) Uani 1 1 d . . . . .
H2A H 0.806(4) 0.176(4) 0.305(2) 0.037 Uiso 1 1 d . U . . .
N3 N 0.7068(4) 0.4235(3) 0.02763(18) 0.0432(8) Uani 1 1 d . . . . .
N4 N 0.9129(3) 0.3045(3) 0.13296(19) 0.0421(8) Uani 1 1 d . . . . .
O1 O 0.8789(3) 0.3967(3) 0.04052(17) 0.0542(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.429(4) . ?
C1 N1 1.476(3) . ?
C1 C1 1.552(5) 3_655 ?
C1 H1 1.0000 . ?
C2 N4 1.293(4) . ?
C2 N2 1.352(3) . ?
C2 C3 1.433(4) . ?
C3 N3 1.298(4) . ?
C3 N1 1.367(4) 3_655 ?
N1 C3 1.367(4) 3_655 ?
N1 H1A 0.86(3) . ?
N2 H2A 0.84(3) . ?
N3 O1 1.408(4) . ?
N4 O1 1.414(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 111.6(2) . . ?
N2 C1 C1 110.8(3) . 3_655 ?
N1 C1 C1 108.00(18) . 3_655 ?
N2 C1 H1 108.8 . . ?
N1 C1 H1 108.8 . . ?
C1 C1 H1 108.8 3_655 . ?
N4 C2 N2 127.8(3) . . ?
N4 C2 C3 110.7(3) . . ?
N2 C2 C3 121.4(3) . . ?
N3 C3 N1 129.1(3) . 3_655 ?
N3 C3 C2 109.8(3) . . ?
N1 C3 C2 121.1(2) 3_655 . ?
C3 N1 C1 112.1(2) 3_655 . ?
C3 N1 H1A 114.3(19) 3_655 . ?
C1 N1 H1A 118(2) . . ?
C2 N2 C1 118.2(2) . . ?
C2 N2 H2A 119(2) . . ?
C1 N2 H2A 119(2) . . ?
C3 N3 O1 104.3(3) . . ?
C2 N4 O1 103.8(3) . . ?
N3 O1 N4 111.3(2) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1864643'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N8 O2'
_chemical_formula_sum            'C6 H2 N8 O2'
_chemical_formula_weight         218.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7793(6)
_cell_length_b                   11.6585(15)
_cell_length_c                   5.7805(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.280(4)
_cell_angle_gamma                90
_cell_volume                     383.23(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    636
_cell_measurement_theta_min      4.59
_cell_measurement_theta_max      24.64

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2200
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.986
_diffrn_reflns_theta_max         25.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             688
_reflns_number_gt                470
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         688
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8267(5) 0.3833(2) 0.6672(5) 0.0165(6) Uani 1 1 d . . . . .
C2 C 1.0701(5) 0.3925(2) 0.6661(5) 0.0162(6) Uani 1 1 d . . . . .
C3 C 1.1292(5) 0.5030(2) 0.9949(5) 0.0148(6) Uani 1 1 d . . . . .
N1 N 0.7308(4) 0.4357(2) 0.8397(4) 0.0183(6) Uani 1 1 d . . . . .
H1 H 0.582(5) 0.435(3) 0.839(5) 0.022 Uiso 1 1 d . U . . .
N2 N 0.7221(4) 0.3234(2) 0.4887(4) 0.0237(6) Uani 1 1 d . . . . .
N3 N 1.1213(4) 0.3399(2) 0.4822(4) 0.0212(6) Uani 1 1 d . . . . .
N4 N 1.2242(4) 0.4515(2) 0.8322(4) 0.0164(6) Uani 1 1 d . . . . .
O1 O 0.9066(3) 0.29503(17) 0.3690(3) 0.0238(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.302(3) . ?
C1 N1 1.369(3) . ?
C1 C2 1.412(4) . ?
C2 N3 1.306(3) . ?
C2 N4 1.372(3) . ?
C3 N4 1.315(3) . ?
C3 N1 1.343(4) 3_767 ?
C3 C3 1.507(5) 3_767 ?
N1 C3 1.343(4) 3_767 ?
N1 H1 0.86(3) . ?
N2 O1 1.410(3) . ?
N3 O1 1.397(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 128.7(2) . . ?
N2 C1 C2 111.1(2) . . ?
N1 C1 C2 120.2(2) . . ?
N3 C2 N4 126.3(2) . . ?
N3 C2 C1 109.8(2) . . ?
N4 C2 C1 123.9(2) . . ?
N4 C3 N1 118.5(2) . 3_767 ?
N4 C3 C3 123.4(3) . 3_767 ?
N1 C3 C3 118.1(3) 3_767 3_767 ?
C3 N1 C1 119.1(2) 3_767 . ?
C3 N1 H1 119.1(19) 3_767 . ?
C1 N1 H1 121.7(19) . . ?
C1 N2 O1 103.3(2) . . ?
C2 N3 O1 104.2(2) . . ?
C3 N4 C2 115.3(2) . . ?
N3 O1 N2 111.63(18) . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1864644'
_audit_update_record             
;
2018-08-30 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N4 O3, 0.67(H2 O)'
_chemical_formula_sum            'C4 H3.33 N4 O3.67'
_chemical_formula_weight         166.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.2788(12)
_cell_length_b                   5.4732(4)
_cell_length_c                   19.4681(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.922(2)
_cell_angle_gamma                90
_cell_volume                     1905.7(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2632
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      25.31

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10735
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.318
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3483
_reflns_number_gt                2354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.6625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3483
_refine_ls_number_parameters     364
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.53539(13) 0.2556(5) 0.88015(13) 0.0185(6) Uani 1 1 d . . . . .
C2A C 0.47517(14) 0.3620(5) 0.82169(13) 0.0190(6) Uani 1 1 d . . . . .
C3A C 0.39180(13) 0.0553(5) 0.82771(13) 0.0193(6) Uani 1 1 d . . . . .
C4A C 0.45692(13) -0.0601(5) 0.89198(13) 0.0179(6) Uani 1 1 d . . . . .
C1B C 0.20159(13) 0.6000(5) 0.95392(13) 0.0191(6) Uani 1 1 d . . . . .
C2B C 0.24632(13) 0.6992(5) 0.91732(13) 0.0169(6) Uani 1 1 d . . . . .
C3B C 0.33267(13) 0.3740(5) 0.95924(13) 0.0183(6) Uani 1 1 d . . . . .
C4B C 0.28571(13) 0.2742(5) 1.00211(13) 0.0179(6) Uani 1 1 d . . . . .
C1C C 0.13408(14) 0.2742(5) 0.23080(14) 0.0227(6) Uani 1 1 d . . . . .
C2C C 0.05727(14) 0.2401(5) 0.18973(14) 0.0219(6) Uani 1 1 d . . . . .
C3C C 0.05464(14) 0.5797(5) 0.11355(14) 0.0215(6) Uani 1 1 d . . . . .
C4C C 0.13893(14) 0.6126(5) 0.15846(14) 0.0233(6) Uani 1 1 d . . . . .
N1A N 0.49667(12) 0.5548(4) 0.79696(12) 0.0286(6) Uani 1 1 d . . . . .
N2A N 0.59584(12) 0.3816(4) 0.89349(12) 0.0274(6) Uani 1 1 d . . . . .
N3A N 0.40460(11) 0.2616(4) 0.79692(11) 0.0221(5) Uani 1 1 d D . . . .
H3AA H 0.3706(12) 0.333(5) 0.7610(12) 0.026 Uiso 1 1 d D U . . .
N4A N 0.52558(11) 0.0469(4) 0.91409(11) 0.0189(5) Uani 1 1 d D . . . .
H4AA H 0.5620(12) -0.019(5) 0.9495(11) 0.023 Uiso 1 1 d D U . . .
N1B N 0.21628(11) 0.8964(4) 0.88205(12) 0.0225(5) Uani 1 1 d . . . . .
N2B N 0.14224(11) 0.7337(4) 0.94114(12) 0.0247(5) Uani 1 1 d . . . . .
N3B N 0.31083(11) 0.5856(4) 0.92081(11) 0.0193(5) Uani 1 1 d D . . . .
H3BA H 0.3410(12) 0.656(4) 0.9034(13) 0.023 Uiso 1 1 d D U . . .
N4B N 0.22177(11) 0.3928(4) 0.99600(12) 0.0209(5) Uani 1 1 d D . . . .
H4BA H 0.1928(13) 0.328(5) 1.0150(13) 0.025 Uiso 1 1 d D U . . .
N1C N 0.03214(12) 0.0524(4) 0.21347(13) 0.0322(6) Uani 1 1 d . . . . .
N2C N 0.15878(13) 0.1066(4) 0.28144(13) 0.0356(6) Uani 1 1 d . . . . .
N3C N 0.01845(11) 0.3963(4) 0.13273(12) 0.0233(5) Uani 1 1 d D . . . .
H3CA H -0.0277(10) 0.364(5) 0.1081(13) 0.028 Uiso 1 1 d D U . . .
N4C N 0.17368(11) 0.4596(4) 0.21541(12) 0.0233(5) Uani 1 1 d D . . . .
H4CA H 0.2208(10) 0.477(5) 0.2414(13) 0.028 Uiso 1 1 d D U . . .
O4 O 0.11917(10) 0.1991(4) 0.04854(11) 0.0251(4) Uani 1 1 d D . . . .
H4A H 0.0749(11) 0.195(5) 0.0140(13) 0.043(9) Uiso 1 1 d D . . . .
H4B H 0.1235(18) 0.054(4) 0.0657(18) 0.068(13) Uiso 1 1 d D . . . .
O1A O 0.57300(10) 0.5720(4) 0.84139(10) 0.0338(5) Uani 1 1 d . . . . .
O2A O 0.33103(9) -0.0483(4) 0.80741(10) 0.0277(5) Uani 1 1 d . . . . .
O3A O 0.44541(9) -0.2454(3) 0.92071(10) 0.0246(4) Uani 1 1 d . . . . .
O1B O 0.15026(9) 0.9239(3) 0.89615(10) 0.0273(4) Uani 1 1 d . . . . .
O2B O 0.38725(9) 0.2582(3) 0.96174(9) 0.0247(4) Uani 1 1 d . . . . .
O3B O 0.30819(9) 0.0913(3) 1.03947(9) 0.0246(4) Uani 1 1 d . . . . .
O1C O 0.09501(11) -0.0360(4) 0.27127(11) 0.0407(5) Uani 1 1 d . . . . .
O2C O 0.02455(9) 0.7223(4) 0.06286(10) 0.0325(5) Uani 1 1 d . . . . .
O3C O 0.17114(10) 0.7782(4) 0.14077(11) 0.0378(5) Uani 1 1 d . . . . .
O5 O 0.2942(5) 0.076(2) 0.1773(4) 0.0371(19) Uani 0.76(3) 1 d D U P A 1
H5A H 0.300(3) 0.078(9) 0.1375(16) 0.045 Uiso 0.76(3) 1 d D U P A 1
H5B H 0.271(2) -0.053(6) 0.178(3) 0.045 Uiso 0.76(3) 1 d D U P A 1
O5' O 0.3145(14) -0.022(6) 0.1816(11) 0.041(4) Uani 0.24(3) 1 d D U P A 2
H5C H 0.315(8) -0.03(3) 0.140(3) 0.049 Uiso 0.24(3) 1 d D U P A 2
H5D H 0.271(3) -0.02(3) 0.178(8) 0.049 Uiso 0.24(3) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N2A 1.295(3) . ?
C1A N4A 1.368(3) . ?
C1A C2A 1.413(3) . ?
C2A N1A 1.291(3) . ?
C2A N3A 1.377(3) . ?
C3A O2A 1.227(3) . ?
C3A N3A 1.344(3) . ?
C3A C4A 1.539(3) . ?
C4A O3A 1.218(3) . ?
C4A N4A 1.362(3) . ?
C1B N2B 1.301(3) . ?
C1B N4B 1.368(3) . ?
C1B C2B 1.416(3) . ?
C2B N1B 1.294(3) . ?
C2B N3B 1.369(3) . ?
C3B O2B 1.214(3) . ?
C3B N3B 1.358(3) . ?
C3B C4B 1.543(3) . ?
C4B O3B 1.218(3) . ?
C4B N4B 1.358(3) . ?
C1C N2C 1.300(3) . ?
C1C N4C 1.368(3) . ?
C1C C2C 1.408(3) . ?
C2C N1C 1.293(3) . ?
C2C N3C 1.379(3) . ?
C3C O2C 1.222(3) . ?
C3C N3C 1.352(3) . ?
C3C C4C 1.542(3) . ?
C4C O3C 1.219(3) . ?
C4C N4C 1.351(3) . ?
N1A O1A 1.404(3) . ?
N2A O1A 1.405(3) . ?
N3A H3AA 0.852(17) . ?
N4A H4AA 0.858(16) . ?
N1B O1B 1.407(3) . ?
N2B O1B 1.406(3) . ?
N3B H3BA 0.867(16) . ?
N4B H4BA 0.854(17) . ?
N1C O1C 1.397(3) . ?
N2C O1C 1.407(3) . ?
N3C H3CA 0.857(16) . ?
N4C H4CA 0.865(17) . ?
O4 H4A 0.867(17) . ?
O4 H4B 0.855(18) . ?
O5 H5A 0.829(19) . ?
O5 H5B 0.83(2) . ?
O5' H5C 0.82(2) . ?
O5' H5D 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2A C1A N4A 128.7(2) . . ?
N2A C1A C2A 110.5(2) . . ?
N4A C1A C2A 120.9(2) . . ?
N1A C2A N3A 127.5(2) . . ?
N1A C2A C1A 110.8(2) . . ?
N3A C2A C1A 121.7(2) . . ?
O2A C3A N3A 123.9(2) . . ?
O2A C3A C4A 117.6(2) . . ?
N3A C3A C4A 118.5(2) . . ?
O3A C4A N4A 122.4(2) . . ?
O3A C4A C3A 118.8(2) . . ?
N4A C4A C3A 118.8(2) . . ?
N2B C1B N4B 127.9(2) . . ?
N2B C1B C2B 110.2(2) . . ?
N4B C1B C2B 121.9(2) . . ?
N1B C2B N3B 128.6(2) . . ?
N1B C2B C1B 110.5(2) . . ?
N3B C2B C1B 120.9(2) . . ?
O2B C3B N3B 123.6(2) . . ?
O2B C3B C4B 117.9(2) . . ?
N3B C3B C4B 118.4(2) . . ?
O3B C4B N4B 123.6(2) . . ?
O3B C4B C3B 117.7(2) . . ?
N4B C4B C3B 118.7(2) . . ?
N2C C1C N4C 127.8(2) . . ?
N2C C1C C2C 110.3(2) . . ?
N4C C1C C2C 121.9(2) . . ?
N1C C2C N3C 128.1(2) . . ?
N1C C2C C1C 110.9(2) . . ?
N3C C2C C1C 121.0(2) . . ?
O2C C3C N3C 124.0(2) . . ?
O2C C3C C4C 117.7(2) . . ?
N3C C3C C4C 118.3(2) . . ?
O3C C4C N4C 123.0(2) . . ?
O3C C4C C3C 117.9(2) . . ?
N4C C4C C3C 119.2(2) . . ?
C2A N1A O1A 103.5(2) . . ?
C1A N2A O1A 103.5(2) . . ?
C3A N3A C2A 120.1(2) . . ?
C3A N3A H3AA 122.3(19) . . ?
C2A N3A H3AA 117.6(18) . . ?
C4A N4A C1A 120.0(2) . . ?
C4A N4A H4AA 118.7(18) . . ?
C1A N4A H4AA 121.3(18) . . ?
C2B N1B O1B 104.11(19) . . ?
C1B N2B O1B 104.00(19) . . ?
C3B N3B C2B 120.3(2) . . ?
C3B N3B H3BA 118.8(17) . . ?
C2B N3B H3BA 120.5(17) . . ?
C4B N4B C1B 119.7(2) . . ?
C4B N4B H4BA 118.8(18) . . ?
C1B N4B H4BA 121.2(18) . . ?
C2C N1C O1C 103.6(2) . . ?
C1C N2C O1C 103.4(2) . . ?
C3C N3C C2C 120.1(2) . . ?
C3C N3C H3CA 122.4(18) . . ?
C2C N3C H3CA 117.3(19) . . ?
C4C N4C C1C 119.5(2) . . ?
C4C N4C H4CA 120.1(19) . . ?
C1C N4C H4CA 120.3(18) . . ?
H4A O4 H4B 102(3) . . ?
N1A O1A N2A 111.65(18) . . ?
N2B O1B N1B 111.14(17) . . ?
N1C O1C N2C 111.79(18) . . ?
H5A O5 H5B 106(3) . . ?
H5C O5' H5D 108(4) . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058

