# 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. 
# 
#######################################################################

data_sad
_database_code_depnum_ccdc_archive 'CCDC 1443747'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1-azaphenalene
_chemical_name_common            'fused heterocycle'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 N O6'
_chemical_formula_weight         473.51

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3361(5)
_cell_length_b                   16.8521(5)
_cell_length_c                   12.0571(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.100(5)
_cell_angle_gamma                90.00
_cell_volume                     2322.38(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      4.67
_cell_measurement_theta_max      62.71

_exptl_crystal_description       plane
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8111
_exptl_absorpt_correction_T_max  0.8723
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      571(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART (Bruker, 1998)'
_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            9906
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         62.77
_reflns_number_total             3646
_reflns_number_gt                3200
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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 > 2sigma(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)+(0.0730P)²+1.7278P] 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         3646
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73640(13) -0.19366(10) 0.65160(13) 0.0326(4) Uani 1 1 d . . .
O2 O 0.65120(15) -0.24642(11) 0.46877(15) 0.0410(4) Uani 1 1 d . . .
O3 O 1.09579(13) 0.02454(9) 0.16925(13) 0.0286(4) Uani 1 1 d . . .
O4 O 0.96591(13) 0.10140(9) 0.20627(14) 0.0302(4) Uani 1 1 d . . .
O5 O 0.60641(12) 0.05718(9) 0.13528(13) 0.0292(4) Uani 1 1 d . . .
O6 O 0.51074(13) -0.01649(11) 0.22328(16) 0.0403(4) Uani 1 1 d . . .
N1 N 1.04455(15) -0.19929(10) 0.56508(15) 0.0258(4) Uani 1 1 d . . .
C1 C 1.15476(18) -0.24092(12) 0.6223(2) 0.0264(5) Uani 1 1 d . . .
C2 C 1.2261(2) -0.22252(14) 0.7378(2) 0.0341(5) Uani 1 1 d . . .
H2A H 1.2045 -0.1835 0.7800 0.041 Uiso 1 1 calc R . .
C3 C 1.3310(2) -0.26308(15) 0.7904(2) 0.0435(6) Uani 1 1 d . . .
H3A H 1.3796 -0.2518 0.8689 0.052 Uiso 1 1 calc R . .
C4 C 1.3636(2) -0.32000(15) 0.7269(3) 0.0443(7) Uani 1 1 d . . .
H4A H 1.4343 -0.3466 0.7626 0.053 Uiso 1 1 calc R . .
C5 C 1.2919(2) -0.33771(14) 0.6110(3) 0.0410(6) Uani 1 1 d . . .
H5A H 1.3146 -0.3760 0.5684 0.049 Uiso 1 1 calc R . .
C6 C 1.1860(2) -0.29854(13) 0.5575(2) 0.0326(5) Uani 1 1 d . . .
H6A H 1.1367 -0.3107 0.4796 0.039 Uiso 1 1 calc R . .
C7 C 0.94669(19) -0.22171(12) 0.58687(18) 0.0257(5) Uani 1 1 d . . .
C8 C 0.84069(18) -0.18857(12) 0.52315(18) 0.0247(5) Uani 1 1 d . . .
C9 C 0.82746(18) -0.12862(12) 0.43270(17) 0.0229(4) Uani 1 1 d . . .
C10 C 0.93126(17) -0.10294(12) 0.41759(17) 0.0211(4) Uani 1 1 d . . .
C11 C 1.04103(18) -0.13794(12) 0.48605(17) 0.0233(4) Uani 1 1 d . . .
C15 C 0.92704(17) -0.04228(11) 0.33397(17) 0.0200(4) Uani 1 1 d . . .
C17 C 0.71657(17) -0.03480(12) 0.28144(17) 0.0222(4) Uani 1 1 d . . .
C16 C 0.81645(17) -0.00946(12) 0.26587(18) 0.0218(4) Uani 1 1 d . . .
H16A H 0.8108 0.0298 0.2097 0.026 Uiso 1 1 calc R . .
C18 C 0.72137(18) -0.09422(12) 0.36418(18) 0.0243(5) Uani 1 1 d . . .
H18A H 0.6532 -0.1106 0.3732 0.029 Uiso 1 1 calc R . .
C13 C 1.13972(18) -0.05191(12) 0.39181(18) 0.0233(4) Uani 1 1 d . . .
C14 C 1.03322(17) -0.01828(12) 0.31995(18) 0.0224(4) Uani 1 1 d . . .
C12 C 1.14173(18) -0.11091(13) 0.47336(19) 0.0257(5) Uani 1 1 d . . .
H12A H 1.2132 -0.1330 0.5210 0.031 Uiso 1 1 calc R . .
C23 C 1.02653(17) 0.04263(12) 0.22928(18) 0.0228(4) Uani 1 1 d . . .
C20 C 0.7339(2) -0.21372(12) 0.54319(18) 0.0267(5) Uani 1 1 d . . .
C19 C 0.9641(2) -0.28389(14) 0.6812(2) 0.0323(5) Uani 1 1 d . . .
H19A H 0.8907 -0.2948 0.6887 0.048 Uiso 1 1 calc R . .
H19B H 1.0193 -0.2651 0.7564 0.048 Uiso 1 1 calc R . .
H19C H 0.9933 -0.3316 0.6588 0.048 Uiso 1 1 calc R . .
C22 C 1.25641(18) -0.02671(14) 0.3889(2) 0.0307(5) Uani 1 1 d . . .
H22A H 1.2442 0.0139 0.3296 0.046 Uiso 1 1 calc R . .
H22B H 1.2937 -0.0716 0.3692 0.046 Uiso 1 1 calc R . .
H22C H 1.3053 -0.0065 0.4660 0.046 Uiso 1 1 calc R . .
C24 C 1.1036(2) 0.08346(14) 0.0852(2) 0.0317(5) Uani 1 1 d . . .
H24A H 1.1234 0.1349 0.1237 0.038 Uiso 1 1 calc R . .
H24B H 1.0296 0.0879 0.0178 0.038 Uiso 1 1 calc R . .
C25 C 1.1977(2) 0.05585(17) 0.0441(2) 0.0420(6) Uani 1 1 d . . .
H25A H 1.2063 0.0933 -0.0121 0.063 Uiso 1 1 calc R . .
H25B H 1.1770 0.0049 0.0062 0.063 Uiso 1 1 calc R . .
H25C H 1.2703 0.0516 0.1117 0.063 Uiso 1 1 calc R . .
C26 C 0.60121(18) 0.00149(12) 0.21252(19) 0.0252(5) Uani 1 1 d . . .
C27 C 0.49695(19) 0.09563(14) 0.0671(2) 0.0338(5) Uani 1 1 d . . .
H27A H 0.5094 0.1343 0.0146 0.051 Uiso 1 1 calc R . .
H27B H 0.4671 0.1214 0.1207 0.051 Uiso 1 1 calc R . .
H27C H 0.4416 0.0567 0.0206 0.051 Uiso 1 1 calc R . .
C21 C 0.6337(2) -0.21541(16) 0.6776(2) 0.0399(6) Uani 1 1 d . . .
H21A H 0.6553 -0.2189 0.7636 0.048 Uiso 1 1 calc R . .
H21B H 0.6059 -0.2672 0.6436 0.048 Uiso 1 1 calc R . .
C28 C 0.5375(2) -0.15596(18) 0.6273(3) 0.0509(7) Uani 1 1 d . . .
H28A H 0.4713 -0.1718 0.6456 0.076 Uiso 1 1 calc R . .
H28B H 0.5150 -0.1531 0.5420 0.076 Uiso 1 1 calc R . .
H28C H 0.5643 -0.1048 0.6618 0.076 Uiso 1 1 calc R . .


_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 C20 1.339(3) . ?
O1 C21 1.462(3) . ?
O2 C20 1.209(3) . ?
O3 C23 1.346(2) . ?
O3 C24 1.448(3) . ?
O4 C23 1.209(3) . ?
O5 C26 1.341(3) . ?
O5 C27 1.444(3) . ?
O6 C26 1.210(3) . ?
N1 C7 1.381(3) . ?
N1 C11 1.396(3) . ?
N1 C1 1.453(3) . ?
C1 C2 1.373(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.378(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.388(3) . ?
C7 C8 1.362(3) . ?
C7 C19 1.501(3) . ?
C8 C9 1.450(3) . ?
C8 C20 1.487(3) . ?
C9 C18 1.385(3) . ?
C9 C10 1.427(3) . ?
C10 C11 1.422(3) . ?
C10 C15 1.423(3) . ?
C11 C12 1.385(3) . ?
C15 C16 1.414(3) . ?
C15 C14 1.440(3) . ?
C17 C16 1.382(3) . ?
C17 C18 1.399(3) . ?
C17 C26 1.483(3) . ?
C13 C12 1.392(3) . ?
C13 C14 1.393(3) . ?
C13 C22 1.514(3) . ?
C14 C23 1.479(3) . ?
C24 C25 1.498(3) . ?
C21 C28 1.496(4) . ?

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
C20 O1 C21 116.27(17) . . ?
C23 O3 C24 116.37(16) . . ?
C26 O5 C27 115.53(16) . . ?
C7 N1 C11 121.85(17) . . ?
C7 N1 C1 120.40(17) . . ?
C11 N1 C1 117.73(17) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 N1 120.06(19) . . ?
C6 C1 N1 118.6(2) . . ?
C1 C2 C3 118.9(2) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 C6 120.1(2) . . ?
C5 C6 C1 118.9(2) . . ?
C8 C7 N1 120.18(19) . . ?
C8 C7 C19 123.12(19) . . ?
N1 C7 C19 116.69(19) . . ?
C7 C8 C9 121.48(19) . . ?
C7 C8 C20 120.82(19) . . ?
C9 C8 C20 117.69(18) . . ?
C18 C9 C10 119.27(18) . . ?
C18 C9 C8 123.64(19) . . ?
C10 C9 C8 117.06(18) . . ?
C11 C10 C15 118.83(18) . . ?
C11 C10 C9 120.30(18) . . ?
C15 C10 C9 120.87(18) . . ?
C12 C11 N1 121.36(18) . . ?
C12 C11 C10 119.83(18) . . ?
N1 C11 C10 118.81(18) . . ?
C16 C15 C10 117.56(18) . . ?
C16 C15 C14 122.92(18) . . ?
C10 C15 C14 119.50(18) . . ?
C16 C17 C18 121.16(19) . . ?
C16 C17 C26 120.87(18) . . ?
C18 C17 C26 117.96(18) . . ?
C17 C16 C15 121.00(18) . . ?
C9 C18 C17 120.13(18) . . ?
C12 C13 C14 119.46(19) . . ?
C12 C13 C22 116.90(18) . . ?
C14 C13 C22 123.63(19) . . ?
C13 C14 C15 119.94(19) . . ?
C13 C14 C23 121.28(18) . . ?
C15 C14 C23 118.77(18) . . ?
C11 C12 C13 122.33(19) . . ?
O4 C23 O3 121.69(19) . . ?
O4 C23 C14 126.58(18) . . ?
O3 C23 C14 111.71(17) . . ?
O2 C20 O1 122.9(2) . . ?
O2 C20 C8 124.14(19) . . ?
O1 C20 C8 112.97(18) . . ?
O3 C24 C25 106.45(18) . . ?
O6 C26 O5 122.49(19) . . ?
O6 C26 C17 124.48(19) . . ?
O5 C26 C17 113.03(17) . . ?
O1 C21 C28 111.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        62.77
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
