# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_MQ-12DA
_audit_block_doi                 10.5517/cc13t7x2
_database_code_depnum_ccdc_archive 'CCDC 1037164'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'6a-methyl-6a,7-dihydrobenzo []phenazin- 5 (6H)-one'
_chemical_name_common            ?
_chemical_melting_point          423
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.518(5)
_cell_length_b                   14.238(5)
_cell_length_c                   25.049(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2681(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    95214
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      25.1

_exptl_crystal_description       rectangular
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   0.2060
_exptl_transmission_factor_max   0.2900
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            95214
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         25.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2381
_reflns_number_gt                2006
_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       'APEX2 (Bruker, 2014.3)'
_computing_cell_refinement       'APEX2 (Bruker, 2014.3);SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0673P)²+1.1139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_restrained_S_all      0.872
_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
N7 N -0.06349(17) 0.28809(9) 0.07953(5) 0.0464(3) Uani 1 1 d . . . . .
O1 O 0.45069(17) 0.11763(10) 0.02872(5) 0.0773(4) Uani 1 1 d . . . . .
N12 N -0.06723(17) 0.18835(9) 0.17388(5) 0.0455(3) Uani 1 1 d . . . . .
C12B C 0.20012(18) 0.10729(9) 0.15179(5) 0.0391(3) Uani 1 1 d . . . . .
C12A C 0.04976(18) 0.16906(9) 0.13813(5) 0.0384(3) Uani 1 1 d . . . . .
C6A C 0.03235(18) 0.19946(9) 0.08016(5) 0.0384(3) Uani 1 1 d . . . . .
C7A C -0.21037(19) 0.29698(9) 0.11181(5) 0.0421(3) Uani 1 1 d . . . . .
C4A C 0.33514(19) 0.08762(10) 0.11472(5) 0.0441(3) Uani 1 1 d . . . . .
C11A C -0.21236(19) 0.24519(10) 0.15958(6) 0.0447(4) Uani 1 1 d . . . . .
C1 C 0.2047(2) 0.06181(10) 0.20102(5) 0.0444(4) Uani 1 1 d . . . . .
H1 H 0.1171 0.0744 0.2263 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3371(2) -0.00131(11) 0.21265(6) 0.0517(4) Uani 1 1 d . . . . .
H2 H 0.3390 -0.0306 0.2458 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3417(2) 0.13749(11) 0.06283(6) 0.0498(4) Uani 1 1 d . . . . .
C6 C 0.2142(2) 0.21678(11) 0.05567(6) 0.0481(4) Uani 1 1 d . . . . .
H6A H 0.1995 0.2286 0.0178 0.058 Uiso 1 1 calc R U . . .
H6B H 0.2648 0.2729 0.0715 0.058 Uiso 1 1 calc R U . . .
C8 C -0.3476(2) 0.35958(11) 0.10139(6) 0.0513(4) Uani 1 1 d . . . . .
H8 H -0.3456 0.3957 0.0705 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4664(2) 0.02247(12) 0.12698(6) 0.0548(4) Uani 1 1 d . . . . .
H4 H 0.5542 0.0087 0.1020 0.066 Uiso 1 1 calc R U . . .
C13 C -0.0661(2) 0.12191(11) 0.04942(6) 0.0501(4) Uani 1 1 d . . . . .
H13A H 0.0018 0.0648 0.0509 0.075 Uiso 1 1 calc R U . . .
H13B H -0.1807 0.1117 0.0653 0.075 Uiso 1 1 calc R U . . .
H13C H -0.0808 0.1407 0.0129 0.075 Uiso 1 1 calc R U . . .
C9 C -0.4870(2) 0.36838(12) 0.13680(7) 0.0584(4) Uani 1 1 d . . . . .
H9 H -0.5789 0.4101 0.1294 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4674(2) -0.02173(12) 0.17562(7) 0.0587(4) Uani 1 1 d . . . . .
H3 H 0.5556 -0.0653 0.1836 0.070 Uiso 1 1 calc R U . . .
C10 C -0.4919(2) 0.31589(12) 0.18315(7) 0.0611(5) Uani 1 1 d . . . . .
H10 H -0.5876 0.3213 0.2065 0.073 Uiso 1 1 calc R U . . .
C11 C -0.3540(2) 0.25541(11) 0.19461(7) 0.0552(4) Uani 1 1 d . . . . .
H11 H -0.3558 0.2211 0.2262 0.066 Uiso 1 1 calc R U . . .
H7N H -0.064(2) 0.3181(11) 0.0478(7) 0.049(4) 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
N7 C7A 1.374(2) . ?
N7 C6A 1.4532(18) . ?
O1 C5 1.2171(19) . ?
N12 C12A 1.2850(18) . ?
N12 C11A 1.405(2) . ?
C12B C1 1.3932(19) . ?
C12B C4A 1.404(2) . ?
C12B C12A 1.472(2) . ?
C12A C6A 1.5207(18) . ?
C6A C6 1.518(2) . ?
C6A C13 1.536(2) . ?
C7A C8 1.388(2) . ?
C7A C11A 1.406(2) . ?
C4A C4 1.389(2) . ?
C4A C5 1.482(2) . ?
C11A C11 1.387(2) . ?
C1 C2 1.372(2) . ?
C2 C3 1.380(2) . ?
C5 C6 1.492(2) . ?
C8 C9 1.379(2) . ?
C4 C3 1.371(2) . ?
C9 C10 1.381(3) . ?
C10 C11 1.378(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
C7A N7 C6A 118.16(12) . . ?
C12A N12 C11A 118.48(12) . . ?
C1 C12B C4A 118.35(13) . . ?
C1 C12B C12A 120.15(13) . . ?
C4A C12B C12A 121.36(12) . . ?
N12 C12A C12B 119.41(12) . . ?
N12 C12A C6A 123.07(12) . . ?
C12B C12A C6A 117.26(12) . . ?
N7 C6A C6 107.51(12) . . ?
N7 C6A C12A 107.47(11) . . ?
C6 C6A C12A 110.77(11) . . ?
N7 C6A C13 112.32(12) . . ?
C6 C6A C13 110.35(12) . . ?
C12A C6A C13 108.39(11) . . ?
N7 C7A C8 123.07(14) . . ?
N7 C7A C11A 117.46(13) . . ?
C8 C7A C11A 119.27(14) . . ?
C4 C4A C12B 120.03(13) . . ?
C4 C4A C5 119.37(14) . . ?
C12B C4A C5 120.58(13) . . ?
C11 C11A N12 119.68(14) . . ?
C11 C11A C7A 119.45(14) . . ?
N12 C11A C7A 120.73(13) . . ?
C2 C1 C12B 120.68(14) . . ?
C1 C2 C3 120.66(14) . . ?
O1 C5 C4A 121.80(14) . . ?
O1 C5 C6 121.60(14) . . ?
C4A C5 C6 116.52(13) . . ?
C5 C6 C6A 114.03(12) . . ?
C9 C8 C7A 120.16(15) . . ?
C3 C4 C4A 120.48(15) . . ?
C8 C9 C10 120.77(15) . . ?
C4 C3 C2 119.77(15) . . ?
C9 C10 C11 119.56(16) . . ?
C10 C11 C11A 120.75(16) . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toulene, Methanol'
