# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_MGG492_0ma
_database_code_depnum_ccdc_archive 'CCDC 1433015'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_MGG492_0ma          
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.879 Note
RESPONSE: Crystal selected for X-ray experiment was small needle  with dimentions 0.084 mm x 0.101 mm x 0.337 mm.
;
_vrf_PLAT183_MGG492_0ma          
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do !
RESPONSE: Crystal selected for X-ray experiment was small needle  with dimentions 0.084 mm x 0.101 mm x 0.337 mm.
;

# Added during the CSD deposition process: Tuesday 2nd of February 2016 02:12:18 AM
# end Validation Reply Form




_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 dipyrrolo[1,2-b:1 ,2 -g][2,6]naphthyridine-5,11-dione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   24.3920(10)
_cell_length_b                   24.3920(10)
_cell_length_c                   4.8236(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2869.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      68.30

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 Crystal selected for X-ray experiment was small needle
 with dimentions 0.084 mm x 0.101 mm x 0.337 mm.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7619
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.624
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.879
_reflns_number_total             1156
_reflns_number_gt                886
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0547P)²+0.3487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1156
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_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 0.57847(6) 0.59543(5) 0.0536(3) 0.0744(5) Uani 1 1 d . . . . .
N1 N 0.58486(6) 0.51559(6) 0.2808(3) 0.0559(4) Uani 1 1 d . . . . .
C1 C 0.63138(9) 0.52824(10) 0.4301(5) 0.0746(6) Uani 1 1 d . . . . .
H1 H 0.6510 0.5609 0.4208 0.090 Uiso 1 1 calc R U . . .
C2 C 0.64340(11) 0.48453(11) 0.5929(5) 0.0860(8) Uani 1 1 d . . . . .
H2 H 0.6729 0.4819 0.7143 0.103 Uiso 1 1 calc R U . . .
C3 C 0.60364(10) 0.44381(10) 0.5466(4) 0.0743(6) Uani 1 1 d . . . . .
H3 H 0.6023 0.4096 0.6318 0.089 Uiso 1 1 calc R U . . .
C4 C 0.56704(8) 0.46342(7) 0.3530(3) 0.0544(5) Uani 1 1 d . . . . .
C5 C 0.51889(8) 0.44133(6) 0.2293(3) 0.0500(4) Uani 1 1 d . . . . .
C6 C 0.49063(7) 0.47231(6) 0.0387(3) 0.0455(4) Uani 1 1 d . . . . .
C7 C 0.55889(7) 0.55021(7) 0.0923(4) 0.0524(4) Uani 1 1 d . . . . .
C8 C 0.50385(10) 0.38420(7) 0.3234(4) 0.0635(5) Uani 1 1 d . . . . .
H8A H 0.4643 0.3815 0.3386 0.076 Uiso 1 1 calc R U . . .
H8B H 0.5193 0.3778 0.5058 0.076 Uiso 1 1 calc R U . . .
C9 C 0.52442(9) 0.34010(7) 0.1252(4) 0.0684(6) Uani 1 1 d . . . . .
H9A H 0.5060 0.3437 -0.0498 0.103 Uiso 1 1 calc R U . . .
H9B H 0.5170 0.3046 0.2020 0.103 Uiso 1 1 calc R U . . .
H9C H 0.5632 0.3443 0.0986 0.103 Uiso 1 1 calc R 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
O1 C7 1.217(2) . ?
N1 C1 1.379(3) . ?
N1 C4 1.389(3) . ?
N1 C7 1.393(2) . ?
C1 C2 1.356(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(3) . ?
C5 C6 1.375(2) . ?
C5 C8 1.511(2) . ?
C6 C7 1.469(3) 9_665 ?
C6 C6 1.474(3) 9_665 ?
C7 C6 1.469(3) 9_665 ?
C8 C9 1.524(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C1 N1 C4 109.37(17) . . ?
C1 N1 C7 125.41(17) . . ?
C4 N1 C7 125.20(15) . . ?
C2 C1 N1 107.7(2) . . ?
C2 C1 H1 126.1 . . ?
N1 C1 H1 126.1 . . ?
C1 C2 C3 108.3(2) . . ?
C1 C2 H2 125.8 . . ?
C3 C2 H2 125.8 . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 106.57(18) . . ?
C3 C4 C5 133.43(19) . . ?
N1 C4 C5 120.00(15) . . ?
C6 C5 C4 119.07(15) . . ?
C6 C5 C8 125.85(18) . . ?
C4 C5 C8 115.07(16) . . ?
C5 C6 C7 119.60(15) . 9_665 ?
C5 C6 C6 121.1(2) . 9_665 ?
C7 C6 C6 119.26(19) 9_665 9_665 ?
O1 C7 N1 118.10(17) . . ?
O1 C7 C6 126.57(18) . 9_665 ?
N1 C7 C6 115.33(15) . 9_665 ?
C5 C8 C9 112.51(15) . . ?
C5 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C4 N1 C1 C2 0.7(2) . . . . ?
C7 N1 C1 C2 179.11(18) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 N1 0.5(2) . . . . ?
C2 C3 C4 C5 -179.14(19) . . . . ?
C1 N1 C4 C3 -0.70(19) . . . . ?
C7 N1 C4 C3 -179.16(15) . . . . ?
C1 N1 C4 C5 178.99(15) . . . . ?
C7 N1 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 179.64(18) . . . . ?
N1 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C5 C8 -0.7(3) . . . . ?
N1 C4 C5 C8 179.70(15) . . . . ?
C4 C5 C6 C7 179.49(13) . . . 9_665 ?
C8 C5 C6 C7 -0.1(2) . . . 9_665 ?
C4 C5 C6 C6 -0.1(3) . . . 9_665 ?
C8 C5 C6 C6 -179.66(17) . . . 9_665 ?
C1 N1 C7 O1 0.2(3) . . . . ?
C4 N1 C7 O1 178.38(16) . . . . ?
C1 N1 C7 C6 -179.21(15) . . . 9_665 ?
C4 N1 C7 C6 -1.0(2) . . . 9_665 ?
C6 C5 C8 C9 83.0(2) . . . . ?
C4 C5 C8 C9 -96.6(2) . . . . ?

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
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645

_refine_diff_density_max         0.098
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.031

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichloroethane/methanol'
