# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_A3_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1873779'
_audit_update_record             
;
2018-10-17 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
16,20-dinitro-(3,4;8,9)-dibenzo-2,7-dioxa-5,10-diaza[4.4.4]propellane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N4 O6'
_chemical_formula_sum            'C18 H16 N4 O6'
_chemical_formula_weight         384.35

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           30
_space_group_name_H-M_alt        'P n c 2'
_space_group_name_Hall           'P 2 -2bc'

_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, z'
'x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'

_cell_length_a                   6.8569(12)
_cell_length_b                   16.734(2)
_cell_length_c                   7.4140(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     850.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    463
_cell_measurement_theta_min      2.4610
_cell_measurement_theta_max      21.9930

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3126
_diffrn_reflns_av_unetI/netI     0.2013
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3126
_reflns_number_gt                1105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.945

_reflns_special_details          
;
 _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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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_abs_structure_details 
;
 Flack x determined using 188 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     153
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1830
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   0.732
_refine_ls_restrained_S_all      0.732
_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 0.8948(11) 0.3002(5) 1.0591(11) 0.047(2) Uani 1 1 d . . . . .
C2 C 0.8865(10) 0.3821(4) 1.0369(11) 0.043(2) Uani 1 1 d . . . . .
H2 H 1.007(9) 0.420(3) 1.070(8) 0.052 Uiso 1 1 d . U . . .
C3 C 0.7237(10) 0.4121(4) 0.9490(11) 0.0381(19) Uani 1 1 d . . . . .
C4 C 0.6000(8) 0.5201(4) 0.7706(12) 0.0384(19) Uani 1 1 d . . . . .
C5 C 0.7144(13) 0.5030(5) 0.5994(12) 0.052(3) Uani 1 1 d . . . . .
H5A H 0.848(10) 0.536(4) 0.602(10) 0.062 Uiso 1 1 d . U . . .
H5B H 0.764(9) 0.444(4) 0.585(9) 0.062 Uiso 1 1 d . U . . .
C6 C 0.5967(13) 0.5222(5) 0.4284(15) 0.067(3) Uani 1 1 d . . . . .
H6A H 0.679(11) 0.508(5) 0.328(9) 0.080 Uiso 1 1 d . U . . .
H6B H 0.578(9) 0.579(4) 0.412(12) 0.080 Uiso 1 1 d . U . . .
C7 C 0.4250(11) 0.6365(4) 0.8862(9) 0.0324(19) Uani 1 1 d . . . . .
C8 C 0.4091(10) 0.7193(4) 0.9128(13) 0.042(2) Uani 1 1 d . . . . .
H8 H 0.511(8) 0.756(4) 0.864(8) 0.050 Uiso 1 1 d . U . . .
C9 C 0.2481(11) 0.7507(5) 0.9990(13) 0.047(2) Uani 1 1 d . . . . .
H9 H 0.232(9) 0.809(4) 1.018(9) 0.056 Uiso 1 1 d . U . . .
N1 N 1.0668(10) 0.2657(5) 1.1431(9) 0.059(2) Uani 1 1 d . . . . .
N2 N 0.5759(9) 0.6052(3) 0.7905(9) 0.0396(18) Uani 1 1 d . . . . .
H2N H 0.693(9) 0.636(3) 0.758(11) 0.06(2) Uiso 1 1 d . . . . .
O1 O 1.1907(8) 0.3106(4) 1.2071(9) 0.092(3) Uani 1 1 d . . . . .
O2 O 1.0817(8) 0.1926(4) 1.1491(8) 0.080(2) Uani 1 1 d . . . . .
O3 O 0.7123(6) 0.4947(3) 0.9275(8) 0.0449(15) 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 C9 1.373(10) 2_665 ?
C1 C2 1.382(10) . ?
C1 N1 1.454(9) . ?
C2 C3 1.386(9) . ?
C2 H2 1.07(6) . ?
C3 C7 1.385(8) 2_665 ?
C3 O3 1.393(7) . ?
C4 N2 1.442(8) . ?
C4 O3 1.458(9) . ?
C4 C5 1.519(10) . ?
C4 C4 1.528(11) 2_665 ?
C5 C6 1.537(13) . ?
C5 H5A 1.07(7) . ?
C5 H5B 1.05(6) . ?
C6 C6 1.521(16) 2_665 ?
C6 H6A 0.97(7) . ?
C6 H6B 0.96(7) . ?
C7 N2 1.360(8) . ?
C7 C3 1.385(8) 2_665 ?
C7 C8 1.404(9) . ?
C8 C9 1.379(10) . ?
C8 H8 0.99(6) . ?
C9 C1 1.373(10) 2_665 ?
C9 H9 1.00(6) . ?
N1 O2 1.227(9) . ?
N1 O1 1.230(8) . ?
N2 H2N 0.98(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 123.2(8) 2_665 . ?
C9 C1 N1 118.1(7) 2_665 . ?
C2 C1 N1 118.6(8) . . ?
C1 C2 C3 116.6(7) . . ?
C1 C2 H2 122(3) . . ?
C3 C2 H2 121(3) . . ?
C7 C3 C2 122.6(6) 2_665 . ?
C7 C3 O3 120.2(7) 2_665 . ?
C2 C3 O3 117.2(6) . . ?
N2 C4 O3 105.5(6) . . ?
N2 C4 C5 109.3(6) . . ?
O3 C4 C5 109.8(5) . . ?
N2 C4 C4 109.4(7) . 2_665 ?
O3 C4 C4 110.2(4) . 2_665 ?
C5 C4 C4 112.4(5) . 2_665 ?
C4 C5 C6 112.2(7) . . ?
C4 C5 H5A 109(4) . . ?
C6 C5 H5A 111(4) . . ?
C4 C5 H5B 115(4) . . ?
C6 C5 H5B 107(4) . . ?
H5A C5 H5B 102(5) . . ?
C6 C6 C5 110.8(5) 2_665 . ?
C6 C6 H6A 113(5) 2_665 . ?
C5 C6 H6A 106(5) . . ?
C6 C6 H6B 112(4) 2_665 . ?
C5 C6 H6B 112(5) . . ?
H6A C6 H6B 103(7) . . ?
N2 C7 C3 120.7(6) . 2_665 ?
N2 C7 C8 120.8(7) . . ?
C3 C7 C8 118.4(7) 2_665 . ?
C9 C8 C7 120.2(7) . . ?
C9 C8 H8 120(4) . . ?
C7 C8 H8 120(4) . . ?
C1 C9 C8 119.0(7) 2_665 . ?
C1 C9 H9 119(4) 2_665 . ?
C8 C9 H9 122(4) . . ?
O2 N1 O1 122.5(8) . . ?
O2 N1 C1 118.6(8) . . ?
O1 N1 C1 118.9(8) . . ?
C7 N2 C4 121.4(6) . . ?
C7 N2 H2N 123(4) . . ?
C4 N2 H2N 113(3) . . ?
C3 O3 C4 114.2(6) . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050



