# 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_ljh039_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1mn7yg
_database_code_depnum_ccdc_archive 'CCDC 1509016'
_audit_update_record             
;
2016-10-09 deposited with the CCDC.
2016-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5,6a,8,8-tetramethyl-10-phenyl-7,8-dihydrophenanthridine-6,9(5H,6aH)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N O2'
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc

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                   10.9689(7)
_cell_length_b                   11.2631(8)
_cell_length_c                   15.5168(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2180(10)
_cell_angle_gamma                90.00
_cell_volume                     1858.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5023
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.21

_exptl_crystal_description       LUMP
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      1.235
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   'SHELXL-97 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22432
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4272
_reflns_number_gt                3134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0638P)²+0.4595P] 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     SHELXL
_refine_ls_extinction_coef       0.0044(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4272
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37828(12) 0.81881(12) 0.84189(9) 0.0413(3) Uani 1 1 d . . .
C1 C 0.32484(14) 0.79013(13) 0.91011(10) 0.0371(3) Uani 1 1 d . . .
O1 O 0.36674(11) 0.71084(10) 0.96256(8) 0.0509(3) Uani 1 1 d . . .
O2 O 0.16343(14) 1.14194(11) 1.07190(9) 0.0613(4) Uani 1 1 d . . .
C2 C 0.20516(13) 0.85846(12) 0.91375(10) 0.0338(3) Uani 1 1 d . . .
C3 C 0.17687(14) 0.84766(13) 1.00499(10) 0.0379(3) Uani 1 1 d . . .
H3A H 0.0865 0.8512 0.9972 0.045 Uiso 1 1 calc R . .
H3B H 0.2047 0.7701 1.0293 0.045 Uiso 1 1 calc R . .
C4 C 0.23750(14) 0.94191(14) 1.07277(10) 0.0376(3) Uani 1 1 d . . .
C5 C 0.19666(14) 1.06155(14) 1.03081(11) 0.0374(3) Uani 1 1 d . . .
C6 C 0.20674(13) 1.07960(13) 0.93735(10) 0.0336(3) Uani 1 1 d . . .
C7 C 0.21749(13) 0.98619(13) 0.88567(10) 0.0329(3) Uani 1 1 d . . .
C8 C 0.24597(14) 0.99347(13) 0.79747(10) 0.0366(3) Uani 1 1 d . . .
C9 C 0.19554(17) 1.07747(15) 0.73295(11) 0.0462(4) Uani 1 1 d . . .
H9 H 0.1426 1.1359 0.7455 0.055 Uiso 1 1 calc R . .
C10 C 0.2226(2) 1.07588(17) 0.65040(12) 0.0583(5) Uani 1 1 d . . .
H10 H 0.1878 1.1325 0.6078 0.070 Uiso 1 1 calc R . .
C11 C 0.3015(2) 0.98955(19) 0.63188(13) 0.0612(5) Uani 1 1 d . . .
H11 H 0.3201 0.9883 0.5765 0.073 Uiso 1 1 calc R . .
C12 C 0.35311(18) 0.90518(17) 0.69440(12) 0.0530(5) Uani 1 1 d . . .
H12 H 0.4065 0.8477 0.6811 0.064 Uiso 1 1 calc R . .
C13 C 0.32578(14) 0.90546(14) 0.77746(11) 0.0394(4) Uani 1 1 d . . .
C14 C 0.48645(17) 0.74755(17) 0.83269(13) 0.0561(5) Uani 1 1 d . . .
H14A H 0.5157 0.7759 0.7830 0.084 Uiso 1 1 calc R . .
H14B H 0.4616 0.6659 0.8232 0.084 Uiso 1 1 calc R . .
H14C H 0.5528 0.7542 0.8859 0.084 Uiso 1 1 calc R . .
C15 C 0.09687(15) 0.79600(15) 0.84517(12) 0.0450(4) Uani 1 1 d . . .
H15A H 0.0893 0.7154 0.8633 0.068 Uiso 1 1 calc R . .
H15B H 0.1151 0.7967 0.7877 0.068 Uiso 1 1 calc R . .
H15C H 0.0194 0.8373 0.8421 0.068 Uiso 1 1 calc R . .
C16 C 0.1926(2) 0.92748(17) 1.15800(12) 0.0547(5) Uani 1 1 d . . .
H16A H 0.2186 0.8514 1.1840 0.082 Uiso 1 1 calc R . .
H16B H 0.1025 0.9329 1.1442 0.082 Uiso 1 1 calc R . .
H16C H 0.2285 0.9891 1.1992 0.082 Uiso 1 1 calc R . .
C17 C 0.38159(15) 0.93726(16) 1.09541(12) 0.0465(4) Uani 1 1 d . . .
H17A H 0.4098 0.8620 1.1221 0.070 Uiso 1 1 calc R . .
H17B H 0.4152 0.9999 1.1363 0.070 Uiso 1 1 calc R . .
H17C H 0.4100 0.9469 1.0420 0.070 Uiso 1 1 calc R . .
C18 C 0.21618(14) 1.20715(13) 0.91326(10) 0.0347(3) Uani 1 1 d . . .
C19 C 0.11167(16) 1.28025(15) 0.89480(13) 0.0516(4) Uani 1 1 d . . .
H19 H 0.0328 1.2484 0.8928 0.062 Uiso 1 1 calc R . .
C20 C 0.1231(2) 1.39967(16) 0.87938(14) 0.0610(5) Uani 1 1 d . . .
H20 H 0.0518 1.4475 0.8663 0.073 Uiso 1 1 calc R . .
C21 C 0.2386(2) 1.44834(16) 0.88319(13) 0.0573(5) Uani 1 1 d . . .
H21 H 0.2460 1.5290 0.8727 0.069 Uiso 1 1 calc R . .
C22 C 0.3427(2) 1.37758(17) 0.90252(14) 0.0608(5) Uani 1 1 d . . .
H22 H 0.4215 1.4104 0.9056 0.073 Uiso 1 1 calc R . .
C23 C 0.33202(16) 1.25783(16) 0.91754(12) 0.0490(4) Uani 1 1 d . . .
H23 H 0.4038 1.2106 0.9307 0.059 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
N1 C1 1.369(2) . ?
N1 C13 1.414(2) . ?
N1 C14 1.468(2) . ?
C1 O1 1.2196(18) . ?
C1 C2 1.535(2) . ?
O2 C5 1.2138(18) . ?
C2 C7 1.519(2) . ?
C2 C3 1.527(2) . ?
C2 C15 1.555(2) . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.516(2) . ?
C4 C16 1.529(2) . ?
C4 C17 1.534(2) . ?
C5 C6 1.495(2) . ?
C6 C7 1.346(2) . ?
C6 C18 1.494(2) . ?
C7 C8 1.479(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.407(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.380(2) . ?
C18 C19 1.383(2) . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.364(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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 C13 122.15(13) . . ?
C1 N1 C14 117.13(14) . . ?
C13 N1 C14 120.46(14) . . ?
O1 C1 N1 121.74(14) . . ?
O1 C1 C2 121.89(14) . . ?
N1 C1 C2 116.29(13) . . ?
C7 C2 C3 113.21(12) . . ?
C7 C2 C1 109.10(12) . . ?
C3 C2 C1 111.38(12) . . ?
C7 C2 C15 109.83(12) . . ?
C3 C2 C15 107.67(12) . . ?
C1 C2 C15 105.34(12) . . ?
C4 C3 C2 115.46(12) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 106.82(12) . . ?
C5 C4 C16 110.01(13) . . ?
C3 C4 C16 110.09(13) . . ?
C5 C4 C17 107.93(13) . . ?
C3 C4 C17 112.59(13) . . ?
C16 C4 C17 109.34(14) . . ?
O2 C5 C6 120.75(14) . . ?
O2 C5 C4 122.19(14) . . ?
C6 C5 C4 116.95(12) . . ?
C7 C6 C18 125.52(13) . . ?
C7 C6 C5 120.66(13) . . ?
C18 C6 C5 113.55(12) . . ?
C6 C7 C8 125.28(13) . . ?
C6 C7 C2 122.87(13) . . ?
C8 C7 C2 111.83(12) . . ?
C9 C8 C13 118.68(14) . . ?
C9 C8 C7 124.56(14) . . ?
C13 C8 C7 116.71(13) . . ?
C10 C9 C8 121.34(16) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 119.36(17) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.71(17) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.39(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.52(15) . . ?
C12 C13 N1 120.64(15) . . ?
C8 C13 N1 119.84(14) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.07(15) . . ?
C23 C18 C6 120.35(14) . . ?
C19 C18 C6 121.28(14) . . ?
C20 C19 C18 120.75(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.42(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.45(17) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.49(18) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.80(17) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?

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
C13 N1 C1 O1 175.93(14) . . . . ?
C14 N1 C1 O1 1.8(2) . . . . ?
C13 N1 C1 C2 -0.8(2) . . . . ?
C14 N1 C1 C2 -174.90(13) . . . . ?
O1 C1 C2 C7 146.19(14) . . . . ?
N1 C1 C2 C7 -37.12(17) . . . . ?
O1 C1 C2 C3 20.49(19) . . . . ?
N1 C1 C2 C3 -162.82(13) . . . . ?
O1 C1 C2 C15 -95.96(17) . . . . ?
N1 C1 C2 C15 80.73(16) . . . . ?
C7 C2 C3 C4 -34.38(17) . . . . ?
C1 C2 C3 C4 89.01(15) . . . . ?
C15 C2 C3 C4 -155.98(13) . . . . ?
C2 C3 C4 C5 55.64(16) . . . . ?
C2 C3 C4 C16 175.05(13) . . . . ?
C2 C3 C4 C17 -62.67(17) . . . . ?
C3 C4 C5 O2 136.75(16) . . . . ?
C16 C4 C5 O2 17.3(2) . . . . ?
C17 C4 C5 O2 -101.95(18) . . . . ?
C3 C4 C5 C6 -47.06(17) . . . . ?
C16 C4 C5 C6 -166.54(13) . . . . ?
C17 C4 C5 C6 74.24(16) . . . . ?
O2 C5 C6 C7 -165.97(15) . . . . ?
C4 C5 C6 C7 17.8(2) . . . . ?
O2 C5 C6 C18 19.7(2) . . . . ?
C4 C5 C6 C18 -156.56(13) . . . . ?
C18 C6 C7 C8 2.8(2) . . . . ?
C5 C6 C7 C8 -170.86(13) . . . . ?
C18 C6 C7 C2 -179.16(13) . . . . ?
C5 C6 C7 C2 7.2(2) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
C1 C2 C7 C6 -123.45(15) . . . . ?
C15 C2 C7 C6 121.57(15) . . . . ?
C3 C2 C7 C8 179.49(12) . . . . ?
C1 C2 C7 C8 54.86(15) . . . . ?
C15 C2 C7 C8 -60.13(16) . . . . ?
C6 C7 C8 C9 -40.9(2) . . . . ?
C2 C7 C8 C9 140.84(15) . . . . ?
C6 C7 C8 C13 141.83(16) . . . . ?
C2 C7 C8 C13 -36.42(17) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 -177.33(16) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C11 C12 C13 N1 179.84(16) . . . . ?
C9 C8 C13 C12 0.6(2) . . . . ?
C7 C8 C13 C12 178.01(14) . . . . ?
C9 C8 C13 N1 -179.94(14) . . . . ?
C7 C8 C13 N1 -2.5(2) . . . . ?
C1 N1 C13 C12 -157.73(15) . . . . ?
C14 N1 C13 C12 16.2(2) . . . . ?
C1 N1 C13 C8 22.8(2) . . . . ?
C14 N1 C13 C8 -163.26(15) . . . . ?
C7 C6 C18 C23 -77.2(2) . . . . ?
C5 C6 C18 C23 96.85(17) . . . . ?
C7 C6 C18 C19 109.29(19) . . . . ?
C5 C6 C18 C19 -76.68(19) . . . . ?
C23 C18 C19 C20 1.3(3) . . . . ?
C6 C18 C19 C20 174.97(17) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 0.1(3) . . . . ?
C19 C18 C23 C22 -0.9(3) . . . . ?
C6 C18 C23 C22 -174.67(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/ethyl acetate'
