# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_shrv449
_database_code_depnum_ccdc_archive 'CCDC 1582630'
_audit_update_record             
;
2017-10-28 deposited with the CCDC.
2018-04-30 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 H4 N8 O6'
_chemical_formula_sum            'C6 H4 N8 O6'
_chemical_formula_weight         284.17

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

_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                   9.5817(10)
_cell_length_b                   10.2973(11)
_cell_length_c                   10.5303(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.562(3)
_cell_angle_gamma                90
_cell_volume                     1029.94(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2282
_cell_measurement_theta_min      2.779
_cell_measurement_theta_max      26.251

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8224
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2101
_reflns_number_gt                1375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0493P)²+0.7328P] 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         2101
_refine_ls_number_parameters     193
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.010
_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
N1 N 1.1328(3) 0.6133(2) 0.8330(2) 0.0326(6) Uani 1 1 d . . . . .
C2 C 1.0373(3) 0.7051(3) 0.8540(2) 0.0265(6) Uani 1 1 d . . . . .
N3 N 1.0732(2) 0.8197(2) 0.9031(2) 0.0310(6) Uani 1 1 d . . . . .
O4 O 0.94789(19) 0.89173(16) 0.90023(18) 0.0305(5) Uani 1 1 d . . . . .
N5 N 0.8365(2) 0.8104(2) 0.8504(2) 0.0254(5) Uani 1 1 d . . . . .
O6 O 0.71504(19) 0.85341(17) 0.84330(18) 0.0293(5) Uani 1 1 d . . . . .
C7 C 0.8886(3) 0.6970(2) 0.8204(2) 0.0238(6) Uani 1 1 d . . . . .
C8 C 0.7939(3) 0.5948(2) 0.7698(2) 0.0248(6) Uani 1 1 d . . . . .
N9 N 0.8136(3) 0.4733(2) 0.8109(2) 0.0307(5) Uani 1 1 d . . . . .
O10 O 0.9065(2) 0.4177(2) 0.8783(2) 0.0407(5) Uani 1 1 d . . . . .
O11 O 0.6938(2) 0.39870(17) 0.7572(2) 0.0373(5) Uani 1 1 d . U . . .
N12 N 0.6031(2) 0.4789(2) 0.6839(2) 0.0333(6) Uani 1 1 d . U . . .
C13 C 0.6624(3) 0.5950(2) 0.6901(3) 0.0253(6) Uani 1 1 d . U . . .
C14 C 0.5891(3) 0.6964(2) 0.6136(2) 0.0237(6) Uani 1 1 d . . . . .
N15 N 0.6545(2) 0.7949(2) 0.5671(2) 0.0252(5) Uani 1 1 d . . . . .
O16 O 0.7793(2) 0.82921(18) 0.57554(18) 0.0301(5) Uani 1 1 d . . . . .
O17 O 0.5542(2) 0.87067(17) 0.49024(18) 0.0319(5) Uani 1 1 d . . . . .
N18 N 0.4218(2) 0.8117(2) 0.4911(2) 0.0325(6) Uani 1 1 d . . . . .
C19 C 0.4438(3) 0.7086(2) 0.5649(3) 0.0270(6) Uani 1 1 d . . . . .
N20 N 0.3396(3) 0.6309(2) 0.5934(3) 0.0344(6) Uani 1 1 d . . . . .
H20A H 0.359(3) 0.556(3) 0.625(3) 0.041 Uiso 1 1 d . U . . .
H20B H 0.256(4) 0.645(3) 0.553(3) 0.041 Uiso 1 1 d . U . . .
H1A H 1.214(4) 0.632(3) 0.867(3) 0.041 Uiso 1 1 d . U . . .
H1B H 1.104(3) 0.529(3) 0.840(3) 0.041 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.355(3) . ?
N1 H1A 0.83(3) . ?
N1 H1B 0.92(3) . ?
C2 N3 1.316(3) . ?
C2 C7 1.424(4) . ?
N3 O4 1.408(3) . ?
O4 N5 1.403(3) . ?
N5 O6 1.239(3) . ?
N5 C7 1.324(3) . ?
C7 C8 1.445(4) . ?
C8 N9 1.329(3) . ?
C8 C13 1.419(4) . ?
N9 O10 1.208(3) . ?
N9 O11 1.434(3) . ?
O11 N12 1.362(3) . ?
N12 C13 1.321(3) . ?
C13 C14 1.444(4) . ?
C14 N15 1.320(3) . ?
C14 C19 1.424(4) . ?
N15 O16 1.239(3) . ?
N15 O17 1.408(3) . ?
O17 N18 1.408(3) . ?
N18 C19 1.316(3) . ?
C19 N20 1.343(3) . ?
N20 H20A 0.85(3) . ?
N20 H20B 0.87(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
C2 N1 H1A 112(2) . . ?
C2 N1 H1B 115.6(19) . . ?
H1A N1 H1B 117(3) . . ?
N3 C2 N1 122.9(3) . . ?
N3 C2 C7 110.6(2) . . ?
N1 C2 C7 126.4(2) . . ?
C2 N3 O4 106.6(2) . . ?
N5 O4 N3 107.33(17) . . ?
O6 N5 C7 133.0(2) . . ?
O6 N5 O4 118.12(19) . . ?
C7 N5 O4 108.9(2) . . ?
N5 C7 C2 106.6(2) . . ?
N5 C7 C8 119.4(2) . . ?
C2 C7 C8 133.9(2) . . ?
N9 C8 C13 105.7(2) . . ?
N9 C8 C7 120.7(3) . . ?
C13 C8 C7 133.1(2) . . ?
O10 N9 C8 134.5(3) . . ?
O10 N9 O11 117.8(2) . . ?
C8 N9 O11 107.7(2) . . ?
N12 O11 N9 108.42(17) . . ?
C13 N12 O11 106.4(2) . . ?
N12 C13 C8 111.8(2) . . ?
N12 C13 C14 116.9(3) . . ?
C8 C13 C14 131.3(2) . . ?
N15 C14 C19 106.7(2) . . ?
N15 C14 C13 122.9(2) . . ?
C19 C14 C13 130.2(2) . . ?
O16 N15 C14 133.9(2) . . ?
O16 N15 O17 117.56(19) . . ?
C14 N15 O17 108.5(2) . . ?
N15 O17 N18 107.74(17) . . ?
C19 N18 O17 106.1(2) . . ?
N18 C19 N20 123.1(3) . . ?
N18 C19 C14 110.9(2) . . ?
N20 C19 C14 125.9(3) . . ?
C19 N20 H20A 120(2) . . ?
C19 N20 H20B 117(2) . . ?
H20A N20 H20B 119(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N3 O4 175.0(2) . . . . ?
C7 C2 N3 O4 -1.3(3) . . . . ?
C2 N3 O4 N5 1.9(3) . . . . ?
N3 O4 N5 O6 177.7(2) . . . . ?
N3 O4 N5 C7 -1.8(3) . . . . ?
O6 N5 C7 C2 -178.4(2) . . . . ?
O4 N5 C7 C2 1.0(3) . . . . ?
O6 N5 C7 C8 -0.9(4) . . . . ?
O4 N5 C7 C8 178.4(2) . . . . ?
N3 C2 C7 N5 0.2(3) . . . . ?
N1 C2 C7 N5 -176.0(2) . . . . ?
N3 C2 C7 C8 -176.7(3) . . . . ?
N1 C2 C7 C8 7.2(5) . . . . ?
N5 C7 C8 N9 -136.5(3) . . . . ?
C2 C7 C8 N9 40.0(4) . . . . ?
N5 C7 C8 C13 33.7(4) . . . . ?
C2 C7 C8 C13 -149.7(3) . . . . ?
C13 C8 N9 O10 178.7(3) . . . . ?
C7 C8 N9 O10 -8.6(4) . . . . ?
C13 C8 N9 O11 -0.4(3) . . . . ?
C7 C8 N9 O11 172.2(2) . . . . ?
O10 N9 O11 N12 -179.4(2) . . . . ?
C8 N9 O11 N12 -0.1(3) . . . . ?
N9 O11 N12 C13 0.6(3) . . . . ?
O11 N12 C13 C8 -0.9(3) . . . . ?
O11 N12 C13 C14 176.7(2) . . . . ?
N9 C8 C13 N12 0.9(3) . . . . ?
C7 C8 C13 N12 -170.5(3) . . . . ?
N9 C8 C13 C14 -176.3(3) . . . . ?
C7 C8 C13 C14 12.4(5) . . . . ?
N12 C13 C14 N15 -150.7(2) . . . . ?
C8 C13 C14 N15 26.3(4) . . . . ?
N12 C13 C14 C19 23.7(4) . . . . ?
C8 C13 C14 C19 -159.3(3) . . . . ?
C19 C14 N15 O16 -177.8(2) . . . . ?
C13 C14 N15 O16 -2.2(4) . . . . ?
C19 C14 N15 O17 0.4(3) . . . . ?
C13 C14 N15 O17 175.9(2) . . . . ?
O16 N15 O17 N18 177.9(2) . . . . ?
C14 N15 O17 N18 -0.5(2) . . . . ?
N15 O17 N18 C19 0.5(3) . . . . ?
O17 N18 C19 N20 176.8(2) . . . . ?
O17 N18 C19 C14 -0.3(3) . . . . ?
N15 C14 C19 N18 -0.1(3) . . . . ?
C13 C14 C19 N18 -175.2(3) . . . . ?
N15 C14 C19 N20 -177.0(3) . . . . ?
C13 C14 C19 N20 7.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N20 H20A O6 0.85(3) 2.24(3) 2.996(3) 147(3) 2_646
N20 H20A N12 0.85(3) 2.47(3) 3.016(4) 123(3) .
N20 H20B N3 0.87(3) 2.23(3) 3.073(4) 165(3) 4_475
N1 H1A N18 0.83(3) 2.31(3) 3.134(4) 171(3) 4_676
N1 H1B O10 0.92(3) 2.29(3) 3.043(3) 139(3) .
N1 H1B O16 0.92(3) 2.45(3) 3.159(3) 134(2) 2_746

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.057

# start Validation Reply Form
_vrf_PLAT015_shrv449             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_js1017a
_database_code_depnum_ccdc_archive 'CCDC 1582631'
_audit_update_record             
;
2017-10-28 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;
_audit_creation_date             2017-10-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 N8 O6'
_chemical_formula_sum            'C6 N8 O6'
_chemical_formula_weight         280.14
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.7033(6)
_cell_length_b                   19.0870(12)
_cell_length_c                   13.1208(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1929.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1624
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.53
_cell_measurement_theta_min      7.06
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.744
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0746 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7865. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             1120
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8363
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.061
_diffrn_reflns_theta_min         2.315
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1834
_reflns_number_total             3191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.164
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.6(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.1619
_refine_ls_R_factor_gt           0.1092
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1930P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2560
_refine_ls_wR_factor_ref         0.3067
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the riding model.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.6(11)
 1.6(11)
2. Same fragment restrains
{O1A, O2A, O3A, O4A, O5A, O6A, N1A, N2A, N3A, N4A, N5A, N6A, N7A, N8A, C1A,
C2A, C3A, C4A, C5A, C6A} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1B, O2B, O3B, O4B, O5B, O6B, N1B, N2B, N3B, N4B, N5B, N6B, N7B, N8B, C1B,
C2B, C3B, C4B, C5B, C6B}
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1A O 0.5367(11) 0.8161(6) 0.7087(10) 0.061(3) Uani 1 1 d D . . . .
O2A O 0.5455(11) 0.8996(5) 0.5832(9) 0.050(2) Uani 1 1 d D . . . .
O3A O 0.3061(15) 0.8832(7) 0.4062(9) 0.067(3) Uani 1 1 d D . . . .
O4A O 0.0525(11) 0.9367(6) 0.4350(8) 0.053(3) Uani 1 1 d D . . . .
O5A O -0.2090(13) 1.0130(4) 0.7052(8) 0.049(2) Uani 1 1 d D . . . .
O6A O -0.2339(11) 0.9303(4) 0.8265(7) 0.039(2) Uani 1 1 d D . . . .
N1A N -0.0272(13) 0.7758(5) 0.7617(9) 0.041(2) Uani 1 1 d D . . . .
N2A N 0.1174(13) 0.7524(5) 0.7430(9) 0.041(2) Uani 1 1 d D . . . .
N3A N 0.4122(15) 0.7742(6) 0.7515(9) 0.053(3) Uani 1 1 d D . . . .
N4A N 0.4563(13) 0.8595(5) 0.6299(9) 0.045(3) Uani 1 1 d D . . . .
N5A N 0.2007(13) 0.8944(6) 0.4701(8) 0.042(2) Uani 1 1 d D . . . .
N6A N -0.0625(13) 0.9445(5) 0.5169(7) 0.041(2) Uani 1 1 d D . . . .
N7A N -0.1678(12) 0.9550(4) 0.7300(7) 0.034(2) Uani 1 1 d D . . . .
N8A N -0.1781(14) 0.8636(5) 0.8396(9) 0.043(2) Uani 1 1 d D . . . .
C1A C 0.2590(14) 0.7911(5) 0.7101(9) 0.032(2) Uani 1 1 d D . . . .
C2A C 0.2844(16) 0.8436(6) 0.6314(10) 0.039(3) Uani 1 1 d D . . . .
C3A C 0.1677(12) 0.8778(6) 0.5656(9) 0.035(3) Uani 1 1 d D . . . .
C4A C 0.0056(13) 0.9091(5) 0.5923(9) 0.031(2) Uani 1 1 d D . . . .
C5A C -0.0720(13) 0.9029(5) 0.6902(9) 0.033(2) Uani 1 1 d D . . . .
C6A C -0.0792(14) 0.8474(5) 0.7627(9) 0.037(3) Uani 1 1 d D . . . .
O1B O 1.0370(16) 0.6968(9) 0.4618(14) 0.115(7) Uani 1 1 d D . . . .
O2B O 1.0627(15) 0.6115(9) 0.3368(13) 0.104(6) Uani 1 1 d D . . . .
O3B O 0.8129(18) 0.6240(8) 0.1585(11) 0.086(4) Uani 1 1 d D . . . .
O4B O 0.5674(15) 0.5659(6) 0.1856(8) 0.065(3) Uani 1 1 d D . . . .
O5B O 0.312(2) 0.4830(6) 0.4520(10) 0.081(4) Uani 1 1 d D . . . .
O6B O 0.2713(13) 0.5653(5) 0.5744(9) 0.051(2) Uani 1 1 d D . . . .
N1B N 0.469(2) 0.7201(6) 0.5148(11) 0.068(4) Uani 1 1 d D . . . .
N2B N 0.6127(18) 0.7458(6) 0.4952(10) 0.059(3) Uani 1 1 d D . . . .
N3B N 0.906(2) 0.7345(8) 0.5038(12) 0.081(5) Uani 1 1 d D . . . .
N4B N 0.9679(16) 0.6504(8) 0.3835(13) 0.076(5) Uani 1 1 d D . . . .
N5B N 0.7094(16) 0.6098(6) 0.2198(10) 0.062(4) Uani 1 1 d D . . . .
N6B N 0.4567(17) 0.5546(7) 0.2675(9) 0.058(3) Uani 1 1 d D . . . .
N7B N 0.3492(15) 0.5415(5) 0.4787(9) 0.048(3) Uani 1 1 d D . . . .
N8B N 0.3209(17) 0.6320(6) 0.5871(10) 0.057(3) Uani 1 1 d D . . . .
C1B C 0.7585(15) 0.7109(6) 0.4624(10) 0.042(3) Uani 1 1 d D . . . .
C2B C 0.7929(17) 0.6606(6) 0.3822(10) 0.047(3) Uani 1 1 d D . . . .
C3B C 0.6809(14) 0.6243(6) 0.3179(10) 0.040(3) Uani 1 1 d D . . . .
C4B C 0.5202(16) 0.5921(5) 0.3430(8) 0.036(3) Uani 1 1 d D . . . .
C5B C 0.4415(16) 0.5949(5) 0.4398(9) 0.040(3) Uani 1 1 d D . . . .
C6B C 0.4210(17) 0.6494(6) 0.5119(10) 0.046(3) Uani 1 1 d 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
O1A N3A 1.370(17) . ?
O1A N4A 1.462(15) . ?
O2A N4A 1.197(14) . ?
O3A N5A 1.186(15) . ?
O4A N5A 1.472(14) . ?
O4A N6A 1.401(14) . ?
O5A N7A 1.197(12) . ?
O6A N7A 1.445(12) . ?
O6A N8A 1.354(12) . ?
N1A N2A 1.225(14) . ?
N1A C6A 1.424(14) . ?
N2A C1A 1.386(15) . ?
N3A C1A 1.339(15) . ?
N4A C2A 1.359(16) . ?
N5A C3A 1.318(16) . ?
N6A C4A 1.307(14) . ?
N7A C5A 1.344(13) . ?
N8A C6A 1.301(16) . ?
C1A C2A 1.452(16) . ?
C2A C3A 1.407(16) . ?
C3A C4A 1.427(14) . ?
C4A C5A 1.422(15) . ?
C5A C6A 1.424(14) . ?
O1B N3B 1.36(2) . ?
O1B N4B 1.46(2) . ?
O2B N4B 1.209(19) . ?
O3B N5B 1.165(17) . ?
O4B N5B 1.449(17) . ?
O4B N6B 1.388(15) . ?
O5B N7B 1.204(13) . ?
O6B N7B 1.465(14) . ?
O6B N8B 1.338(14) . ?
N1B N2B 1.235(18) . ?
N1B C6B 1.399(17) . ?
N2B C1B 1.375(17) . ?
N3B C1B 1.337(17) . ?
N4B C2B 1.362(17) . ?
N5B C3B 1.335(18) . ?
N6B C4B 1.317(16) . ?
N7B C5B 1.344(14) . ?
N8B C6B 1.295(18) . ?
C1B C2B 1.449(18) . ?
C2B C3B 1.391(17) . ?
C3B C4B 1.421(16) . ?
C4B C5B 1.408(16) . ?
C5B C6B 1.415(15) . ?

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
N3A O1A N4A 108.9(9) . . ?
N6A O4A N5A 108.0(8) . . ?
N8A O6A N7A 107.8(8) . . ?
N2A N1A C6A 127.4(10) . . ?
N1A N2A C1A 125.7(9) . . ?
C1A N3A O1A 108.0(10) . . ?
O2A N4A O1A 118.7(10) . . ?
O2A N4A C2A 135.2(12) . . ?
C2A N4A O1A 106.0(10) . . ?
O3A N5A O4A 114.2(11) . . ?
O3A N5A C3A 139.5(13) . . ?
C3A N5A O4A 106.2(9) . . ?
C4A N6A O4A 105.8(9) . . ?
O5A N7A O6A 116.6(9) . . ?
O5A N7A C5A 136.4(11) . . ?
C5A N7A O6A 107.0(8) . . ?
C6A N8A O6A 108.1(10) . . ?
N2A C1A C2A 134.1(10) . . ?
N3A C1A N2A 116.0(11) . . ?
N3A C1A C2A 109.7(10) . . ?
N4A C2A C1A 107.2(10) . . ?
N4A C2A C3A 120.7(11) . . ?
C3A C2A C1A 132.1(11) . . ?
N5A C3A C2A 124.9(11) . . ?
N5A C3A C4A 107.5(10) . . ?
C2A C3A C4A 127.1(11) . . ?
N6A C4A C3A 112.4(10) . . ?
N6A C4A C5A 123.9(9) . . ?
C5A C4A C3A 123.6(10) . . ?
N7A C5A C4A 121.3(9) . . ?
N7A C5A C6A 105.6(10) . . ?
C4A C5A C6A 133.0(10) . . ?
N1A C6A C5A 134.1(11) . . ?
N8A C6A N1A 113.6(10) . . ?
N8A C6A C5A 111.3(10) . . ?
N3B O1B N4B 109.7(11) . . ?
N6B O4B N5B 108.3(10) . . ?
N8B O6B N7B 106.5(9) . . ?
N2B N1B C6B 128.0(13) . . ?
N1B N2B C1B 127.0(12) . . ?
C1B N3B O1B 106.7(13) . . ?
O2B N4B O1B 120.7(14) . . ?
O2B N4B C2B 132.8(16) . . ?
C2B N4B O1B 106.5(13) . . ?
O3B N5B O4B 115.9(15) . . ?
O3B N5B C3B 137.0(17) . . ?
C3B N5B O4B 107.1(10) . . ?
C4B N6B O4B 105.7(11) . . ?
O5B N7B O6B 116.1(11) . . ?
O5B N7B C5B 136.0(13) . . ?
C5B N7B O6B 107.8(9) . . ?
C6B N8B O6B 108.7(11) . . ?
N2B C1B C2B 134.3(11) . . ?
N3B C1B N2B 113.7(13) . . ?
N3B C1B C2B 111.3(13) . . ?
N4B C2B C1B 105.4(12) . . ?
N4B C2B C3B 123.4(13) . . ?
C3B C2B C1B 131.1(12) . . ?
N5B C3B C2B 125.9(12) . . ?
N5B C3B C4B 106.1(11) . . ?
C2B C3B C4B 127.9(12) . . ?
N6B C4B C3B 112.6(10) . . ?
N6B C4B C5B 122.6(11) . . ?
C5B C4B C3B 124.6(10) . . ?
N7B C5B C4B 122.8(10) . . ?
N7B C5B C6B 104.2(11) . . ?
C4B C5B C6B 132.8(11) . . ?
N1B C6B C5B 134.1(13) . . ?
N8B C6B N1B 112.7(11) . . ?
N8B C6B C5B 112.7(11) . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id He931
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.6(11)
2 1.6(11)

