# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_tgbv22cx
_database_code_depnum_ccdc_archive 'CCDC 1003266'
_audit_update_record             
;
2014-05-14 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N4 O4'
_chemical_formula_sum            'C22 H14 N4 O4'
_chemical_formula_weight         398.37

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4715(5)
_cell_length_b                   6.6057(7)
_cell_length_c                   16.7243(18)
_cell_angle_alpha                101.339(9)
_cell_angle_beta                 91.268(9)
_cell_angle_gamma                105.658(10)
_cell_volume                     464.89(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    774
_cell_measurement_theta_min      3.6687
_cell_measurement_theta_max      29.3942

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             206
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_T_max  1.0452
_exptl_absorpt_process_details   
;
 ?
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3596
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.1490
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         29.46
_reflns_number_total             2159
_reflns_number_gt                990
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2159
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_restrained_S_all      0.807
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1489(5) 0.9108(3) 0.23696(12) 0.0163(5) Uani 1 1 d . . .
C2 C 0.2941(5) 0.7493(3) 0.23603(13) 0.0161(5) Uani 1 1 d . . .
H2 H 0.3666 0.7240 0.2860 0.019 Uiso 1 1 calc R . .
C3 C 0.3328(4) 0.6257(3) 0.16238(12) 0.0139(5) Uani 1 1 d . . .
C4 C 0.2327(5) 0.6598(3) 0.08816(13) 0.0169(5) Uani 1 1 d . . .
H4 H 0.2658 0.5751 0.0381 0.020 Uiso 1 1 calc R . .
C5 C 0.0854(4) 0.8173(3) 0.08799(12) 0.0171(5) Uani 1 1 d . . .
H5 H 0.0156 0.8407 0.0374 0.021 Uiso 1 1 calc R . .
C6 C 0.0368(4) 0.9441(3) 0.16172(13) 0.0165(5) Uani 1 1 d . . .
C7 C 0.1077(5) 1.0482(4) 0.31074(13) 0.0193(5) Uani 1 1 d . . .
C8 C 0.0670(5) 1.1765(4) 0.36801(13) 0.0227(6) Uani 1 1 d . . .
C9 C 0.0302(5) 1.3383(4) 0.43524(13) 0.0221(6) Uani 1 1 d . . .
C10 C -0.0929(5) 1.5030(4) 0.42081(14) 0.0285(6) Uani 1 1 d . . .
H10 H -0.1564 1.5052 0.3665 0.034 Uiso 1 1 calc R . .
C11 C 0.1229(5) 1.3377(4) 0.51509(13) 0.0288(6) Uani 1 1 d . . .
H11 H 0.2072 1.2272 0.5257 0.035 Uiso 1 1 calc R . .
N1 N -0.1104(4) 1.0983(3) 0.16162(14) 0.0216(5) Uani 1 1 d . . .
N2 N 0.4831(4) 0.4566(3) 0.16186(11) 0.0187(5) Uani 1 1 d . . .
O1 O 0.5126(3) 0.3459(2) 0.09487(9) 0.0220(4) Uani 1 1 d . . .
O2 O 0.5754(3) 0.4285(2) 0.22809(9) 0.0237(4) Uani 1 1 d . . .
H1A H -0.157(5) 1.166(4) 0.2083(15) 0.044(8) Uiso 1 1 d . . .
H1B H -0.204(5) 1.111(4) 0.1137(15) 0.045(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0151(12) 0.0156(12) 0.0184(13) -0.0001(10) 0.0026(10) 0.0074(11)
C2 0.0187(12) 0.0167(12) 0.0137(12) 0.0034(10) 0.0002(9) 0.0060(10)
C3 0.0132(11) 0.0132(12) 0.0171(12) 0.0022(10) 0.0007(9) 0.0075(10)
C4 0.0187(12) 0.0164(13) 0.0166(12) 0.0012(10) 0.0013(9) 0.0082(11)
C5 0.0177(12) 0.0201(13) 0.0158(12) 0.0046(10) -0.0020(9) 0.0087(11)
C6 0.0135(12) 0.0150(13) 0.0216(13) 0.0028(11) 0.0018(9) 0.0056(11)
C7 0.0220(13) 0.0182(13) 0.0207(13) 0.0054(11) 0.0029(10) 0.0092(11)
C8 0.0243(13) 0.0264(14) 0.0194(13) 0.0043(11) 0.0018(10) 0.0107(12)
C9 0.0249(13) 0.0221(13) 0.0209(13) -0.0012(11) 0.0038(10) 0.0132(11)
C10 0.0387(15) 0.0324(15) 0.0171(13) -0.0002(11) 0.0011(11) 0.0181(13)
C11 0.0422(16) 0.0276(15) 0.0229(14) 0.0017(12) 0.0016(11) 0.0230(13)
N1 0.0245(12) 0.0204(12) 0.0246(13) 0.0056(10) 0.0023(10) 0.0138(10)
N2 0.0176(11) 0.0179(11) 0.0225(11) 0.0055(9) 0.0033(8) 0.0071(9)
O1 0.0287(9) 0.0217(9) 0.0188(9) 0.0015(7) 0.0068(7) 0.0141(8)
O2 0.0288(9) 0.0237(10) 0.0229(9) 0.0061(8) -0.0032(7) 0.0143(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.388(3) . ?
C1 C6 1.422(3) . ?
C1 C7 1.428(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 N2 1.450(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.354(3) . ?
C7 C8 1.201(3) . ?
C8 C9 1.437(3) . ?
C9 C11 1.391(3) . ?
C9 C10 1.402(3) . ?
C10 C11 1.383(3) 2_586 ?
C10 H10 0.9500 . ?
C11 C10 1.383(3) 2_586 ?
C11 H11 0.9500 . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.93(3) . ?
N2 O2 1.238(2) . ?
N2 O1 1.242(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 C1 C6 119.37(19) . . ?
C2 C1 C7 122.8(2) . . ?
C6 C1 C7 117.79(18) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.64(19) . . ?
C2 C3 N2 119.54(19) . . ?
C4 C3 N2 118.82(18) . . ?
C5 C4 C3 119.30(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C5 120.8(2) . . ?
N1 C6 C1 120.13(19) . . ?
C5 C6 C1 119.07(18) . . ?
C8 C7 C1 173.6(2) . . ?
C7 C8 C9 177.1(2) . . ?
C11 C9 C10 119.0(2) . . ?
C11 C9 C8 120.8(2) . . ?
C10 C9 C8 120.2(2) . . ?
C11 C10 C9 120.6(2) 2_586 . ?
C11 C10 H10 119.7 2_586 . ?
C9 C10 H10 119.7 . . ?
C10 C11 C9 120.4(2) 2_586 . ?
C10 C11 H11 119.8 2_586 . ?
C9 C11 H11 119.8 . . ?
C6 N1 H1A 119.3(16) . . ?
C6 N1 H1B 121.0(15) . . ?
H1A N1 H1B 118(2) . . ?
O2 N2 O1 122.98(18) . . ?
O2 N2 C3 118.61(17) . . ?
O1 N2 C3 118.41(17) . . ?

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
C6 C1 C2 C3 1.1(3) . . . . ?
C7 C1 C2 C3 -178.5(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 N2 -179.67(19) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
N2 C3 C4 C5 178.94(19) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 N1 -179.5(2) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C2 C1 C6 N1 178.8(2) . . . . ?
C7 C1 C6 N1 -1.6(3) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C7 C1 C6 C5 177.4(2) . . . . ?
C2 C1 C7 C8 164(2) . . . . ?
C6 C1 C7 C8 -15(2) . . . . ?
C1 C7 C8 C9 -56(6) . . . . ?
C7 C8 C9 C11 -111(5) . . . . ?
C7 C8 C9 C10 68(5) . . . . ?
C11 C9 C10 C11 -0.2(4) . . . 2_586 ?
C8 C9 C10 C11 -178.5(2) . . . 2_586 ?
C10 C9 C11 C10 0.2(4) . . . 2_586 ?
C8 C9 C11 C10 178.5(2) . . . 2_586 ?
C2 C3 N2 O2 -0.5(3) . . . . ?
C4 C3 N2 O2 179.12(18) . . . . ?
C2 C3 N2 O1 179.27(19) . . . . ?
C4 C3 N2 O1 -1.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.836
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
