# 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 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_14_sq
_database_code_depnum_ccdc_archive 'CCDC 1819778'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT415_14_sq               
;
PROBLEM: Short Inter D-H..H-X       H1B    ..  H11     ..       1.73 Ang.  
RESPONSE: H1B was added in a calculated position.  H1B hydrogen bonds with 
N4 on a neighboring molecule.  This H bonding leads to a short H1B...H11 
contact.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
13-imino-7,13-dihydro-6H-quinazolino[3,4-a]quinazolin-6-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N4 O'
_chemical_formula_sum            'C15 H10 N4 O'
_chemical_formula_weight         262.27

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                   4.9412(3)
_cell_length_b                   16.3951(11)
_cell_length_c                   16.2626(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.079(2)
_cell_angle_gamma                90
_cell_volume                     1316.59(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    4741
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.98
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5085
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      102(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13971
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.783
_diffrn_reflns_theta_max         25.347
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2401
_reflns_number_gt                1773
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL v2014-4 (Bruker, 2014)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the unambiguous space group.  The space group 
choice was confirmed by successful convergence of the full-matrix 
least-squares refinement on F².  The final map had no significant 
features.  A final analysis of variance between observed and calculated 
structure factors showed some dependence on amplitude and little 
dependence on resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.8303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2401
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.139
_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 0.6319(3) 0.80308(11) 0.93370(9) 0.0254(4) Uani 1 1 d . . . . .
N4 N 0.5641(4) 0.72360(14) 0.55823(11) 0.0305(6) Uani 1 1 d . . . . .
H4A H 0.4445 0.6898 0.5431 0.046 Uiso 1 1 calc R U . . .
N1 N 0.3457(4) 0.69608(12) 0.93172(10) 0.0208(5) Uani 1 1 d . . . . .
H1B H 0.3256 0.6991 0.9852 0.025 Uiso 1 1 calc R U . . .
N2 N 0.4190(4) 0.67667(12) 0.68072(10) 0.0189(4) Uani 1 1 d . . . . .
N3 N 0.5734(3) 0.73435(11) 0.80901(10) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.5180(4) 0.74602(15) 0.89710(12) 0.0192(5) Uani 1 1 d . . . . .
C2 C 0.1987(4) 0.64023(14) 0.88745(13) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.0065(5) 0.59153(15) 0.92727(14) 0.0237(6) Uani 1 1 d . . . . .
H3 H -0.0090 0.5950 0.9852 0.028 Uiso 1 1 calc R U . . .
C4 C -0.1564(5) 0.53961(15) 0.88263(14) 0.0248(6) Uani 1 1 d . . . . .
H4 H -0.2865 0.5079 0.9099 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1359(4) 0.53209(14) 0.79731(14) 0.0233(5) Uani 1 1 d . . . . .
H5 H -0.2510 0.4955 0.7672 0.028 Uiso 1 1 calc R U . . .
C6 C 0.0517(4) 0.57795(14) 0.75738(13) 0.0200(5) Uani 1 1 d . . . . .
H6 H 0.0667 0.5731 0.6995 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2212(4) 0.63190(14) 0.80228(12) 0.0173(5) Uani 1 1 d . . . . .
C8 C 0.4138(4) 0.68258(14) 0.76185(12) 0.0157(5) Uani 1 1 d . . . . .
C9 C 0.5855(4) 0.72490(14) 0.63963(12) 0.0187(5) Uani 1 1 d . . . . .
C10 C 0.7767(4) 0.77768(14) 0.68277(12) 0.0164(5) Uani 1 1 d . . . . .
C11 C 0.9655(4) 0.82419(14) 0.64002(13) 0.0190(5) Uani 1 1 d . . . . .
H11 H 0.9670 0.8214 0.5817 0.023 Uiso 1 1 calc R U . . .
C12 C 1.1470(4) 0.87341(15) 0.68193(13) 0.0212(5) Uani 1 1 d . . . . .
H12 H 1.2714 0.9058 0.6530 0.025 Uiso 1 1 calc R U . . .
C13 C 1.1467(4) 0.87539(14) 0.76704(13) 0.0209(5) Uani 1 1 d . . . . .
H13 H 1.2756 0.9085 0.7962 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9646(4) 0.83060(14) 0.81062(13) 0.0184(5) Uani 1 1 d . . . . .
H14 H 0.9697 0.8328 0.8690 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7716(4) 0.78175(13) 0.76887(12) 0.0153(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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX2 (Bruker, 2014).  Four 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2014) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

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 C1 1.234(3) . ?
N4 C9 1.324(3) . ?
N4 H4A 0.8400 . ?
N1 C1 1.321(3) . ?
N1 C2 1.359(3) . ?
N1 H1B 0.8800 . ?
N2 C8 1.324(3) . ?
N2 C9 1.337(3) . ?
N3 C8 1.374(3) . ?
N3 C15 1.427(3) . ?
N3 C1 1.481(2) . ?
C2 C7 1.400(3) . ?
C2 C3 1.416(3) . ?
C3 C4 1.363(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.440(3) . ?
C9 C10 1.444(3) . ?
C10 C15 1.403(3) . ?
C10 C11 1.408(3) . ?
C11 C12 1.369(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9500 . ?

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 N4 H4A 109.5 . . ?
C1 N1 C2 122.13(18) . . ?
C1 N1 H1B 118.9 . . ?
C2 N1 H1B 118.9 . . ?
C8 N2 C9 119.29(19) . . ?
C8 N3 C15 118.08(17) . . ?
C8 N3 C1 119.84(17) . . ?
C15 N3 C1 121.76(18) . . ?
O1 C1 N1 123.64(19) . . ?
O1 C1 N3 117.88(19) . . ?
N1 C1 N3 118.5(2) . . ?
N1 C2 C7 122.0(2) . . ?
N1 C2 C3 119.50(19) . . ?
C7 C2 C3 118.4(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 120.6(2) . . ?
C2 C7 C8 118.2(2) . . ?
C6 C7 C8 121.16(18) . . ?
N2 C8 N3 124.8(2) . . ?
N2 C8 C7 116.73(19) . . ?
N3 C8 C7 118.49(18) . . ?
N4 C9 N2 117.5(2) . . ?
N4 C9 C10 121.5(2) . . ?
N2 C9 C10 121.00(18) . . ?
C15 C10 C11 120.2(2) . . ?
C15 C10 C9 118.56(19) . . ?
C11 C10 C9 121.21(18) . . ?
C12 C11 C10 120.46(19) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.07(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 118.30(19) . . ?
C14 C15 N3 123.76(18) . . ?
C10 C15 N3 117.92(19) . . ?

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
N4 H4A O1 0.84 2.32 2.922(3) 129.4 4_575
N1 H1B N4 0.88 2.19 2.848(3) 131.2 4_576

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.059



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
