# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1062055'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
6-imino-1,3,8-trimethyl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile
_chemical_name_common            
6-imino-1,3,8-trimethyl-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitrile
_chemical_melting_point          130
_chemical_formula_moiety         'C12 H12 N4 O2'
_chemical_formula_sum            'C12 H12 N4 O2'
_chemical_formula_weight         244.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 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'

_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                   7.534(3)
_cell_length_b                   10.682(4)
_cell_length_c                   16.411(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.32(3)
_cell_angle_gamma                90
_cell_volume                     1290.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      29
_cell_measurement_theta_max      38

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2506
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.975
_diffrn_reflns_theta_max         73.797
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2425
_reflns_number_gt                2099
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0676P)²+0.3358P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0119(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2425
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.17780(16) 0.24403(11) 0.72419(6) 0.0505(3) Uani 1 1 d . . . . .
O2 O 0.14736(15) 0.42890(11) 0.79692(7) 0.0493(3) Uani 1 1 d . . . . .
N1 N -0.0453(2) 0.59367(13) 0.74166(10) 0.0528(4) Uani 1 1 d . . . . .
N2 N -0.2893(3) 0.12531(19) 0.58817(12) 0.0843(6) Uani 1 1 d . . . . .
N3 N -0.2094(3) 0.49721(17) 0.52364(11) 0.0750(5) Uani 1 1 d . . . . .
N4 N -0.4826(2) 0.43714(19) 0.70392(13) 0.0736(5) Uani 1 1 d . . . . .
C2 C 0.1060(2) 0.30657(16) 0.64791(9) 0.0458(4) Uani 1 1 d . . . . .
C3 C -0.1045(2) 0.32762(14) 0.63816(9) 0.0428(4) Uani 1 1 d . . . . .
C4 C -0.1429(2) 0.37317(15) 0.72420(9) 0.0416(4) Uani 1 1 d . . . . .
C5 C -0.0736(2) 0.27331(15) 0.79080(10) 0.0463(4) Uani 1 1 d . . . . .
C6 C 0.1290(2) 0.29406(16) 0.79668(9) 0.0484(4) Uani 1 1 d . . . . .
C7 C -0.0118(2) 0.48047(15) 0.75483(9) 0.0422(4) Uani 1 1 d . . . . .
C8 C 0.1543(4) 0.2300(2) 0.57889(12) 0.0638(5) Uani 1 1 d . . . . .
C9 C -0.1360(3) 0.2961(2) 0.87187(12) 0.0605(5) Uani 1 1 d . . . . .
C10 C 0.2606(3) 0.2413(3) 0.87077(12) 0.0699(6) Uani 1 1 d . . . . .
C11 C -0.1638(2) 0.42339(16) 0.57332(10) 0.0492(4) Uani 1 1 d . . . . .
C12 C -0.2089(3) 0.21292(17) 0.61125(10) 0.0529(4) Uani 1 1 d . . . . .
C13 C -0.3332(2) 0.40986(16) 0.71438(11) 0.0511(4) Uani 1 1 d . . . . .
H1 H 0.061(3) 0.638(2) 0.7686(16) 0.084(7) Uiso 1 1 d . . . . .
H2 H 0.160(2) 0.3915(19) 0.6485(12) 0.054(5) Uiso 1 1 d . . . . .
H5 H -0.109(3) 0.1929(18) 0.7707(11) 0.049(5) Uiso 1 1 d . . . . .
H8 H 0.294(4) 0.232(2) 0.5891(16) 0.090(8) Uiso 1 1 d . . . . .
H81 H 0.108(3) 0.147(2) 0.5823(15) 0.081(7) Uiso 1 1 d . . . . .
H82 H 0.102(3) 0.268(2) 0.5251(16) 0.083(7) Uiso 1 1 d . . . . .
H9 H -0.271(4) 0.291(2) 0.8594(15) 0.084(7) Uiso 1 1 d . . . . .
H91 H -0.091(3) 0.228(2) 0.9142(14) 0.074(6) Uiso 1 1 d . . . . .
H92 H -0.093(3) 0.379(2) 0.8967(15) 0.080(7) Uiso 1 1 d . . . . .
H10 H 0.236(3) 0.280(2) 0.9212(16) 0.078(7) Uiso 1 1 d . . . . .
H101 H 0.229(4) 0.148(3) 0.8706(18) 0.103(9) Uiso 1 1 d . . . . .
H102 H 0.393(5) 0.262(3) 0.8653(18) 0.111(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4202(18) . ?
O1 C6 1.4225(19) . ?
O2 C7 1.3656(19) . ?
O2 C6 1.447(2) . ?
N1 C7 1.245(2) . ?
N2 C12 1.135(2) . ?
N3 C11 1.134(2) . ?
N4 C13 1.140(2) . ?
C2 C8 1.503(3) . ?
C2 C3 1.576(2) . ?
C3 C12 1.472(2) . ?
C3 C11 1.475(2) . ?
C3 C4 1.577(2) . ?
C4 C13 1.462(2) . ?
C4 C7 1.526(2) . ?
C4 C5 1.537(2) . ?
C5 C9 1.522(2) . ?
C5 C6 1.525(3) . ?
C6 C10 1.505(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
C2 O1 C6 116.27(12) . . ?
C7 O2 C6 109.08(12) . . ?
O1 C2 C8 107.49(15) . . ?
O1 C2 C3 110.02(13) . . ?
C8 C2 C3 113.66(15) . . ?
C12 C3 C11 107.49(13) . . ?
C12 C3 C2 111.94(14) . . ?
C11 C3 C2 108.40(13) . . ?
C12 C3 C4 109.69(13) . . ?
C11 C3 C4 110.29(13) . . ?
C2 C3 C4 109.01(12) . . ?
C13 C4 C7 112.66(14) . . ?
C13 C4 C5 116.15(14) . . ?
C7 C4 C5 100.92(12) . . ?
C13 C4 C3 110.29(13) . . ?
C7 C4 C3 107.29(13) . . ?
C5 C4 C3 108.86(13) . . ?
C9 C5 C6 114.39(15) . . ?
C9 C5 C4 112.92(15) . . ?
C6 C5 C4 97.32(13) . . ?
O1 C6 O2 109.54(13) . . ?
O1 C6 C10 106.95(15) . . ?
O2 C6 C10 108.93(16) . . ?
O1 C6 C5 109.06(13) . . ?
O2 C6 C5 103.82(13) . . ?
C10 C6 C5 118.35(17) . . ?
N1 C7 O2 127.10(15) . . ?
N1 C7 C4 125.42(15) . . ?
O2 C7 C4 107.47(13) . . ?
N3 C11 C3 179.8(2) . . ?
N2 C12 C3 178.00(19) . . ?
N4 C13 C4 177.6(2) . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'evaporation chloroform solution at room temperature '
