# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_yogesh_a
_audit_block_doi                 10.5517/ccdc.csd.cc1yzvj9
_database_code_depnum_ccdc_archive 'CCDC 1817112'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        6-(4-methoxyphenyl)phenanthridine
_chemical_name_common            phenanthridine
_chemical_melting_point          ?
_chemical_formula_moiety         C20H15NO
_chemical_formula_sum            'C20 H15 N O'
_chemical_formula_weight         285.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   13.107(3)
_cell_length_b                   5.8099(12)
_cell_length_c                   19.648(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.575(7)
_cell_angle_gamma                90
_cell_volume                     1460.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8202
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      23.59

_exptl_crystal_description       cube
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29074
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.185
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2948
_reflns_number_gt                1629
_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    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0597P)²+0.3631P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0107(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 0.84544(10) 0.3855(3) 0.66436(7) 0.0631(5) Uani 1 1 d . . . . .
N1 N 0.37395(12) 0.5982(3) 0.65302(8) 0.0478(5) Uani 1 1 d . . . . .
C13 C 0.40656(14) 0.4256(3) 0.62066(9) 0.0435(5) Uani 1 1 d . . . . .
C1 C 0.33744(15) 0.2659(3) 0.57717(9) 0.0441(5) Uani 1 1 d . . . . .
C14 C 0.52214(14) 0.4046(3) 0.63081(9) 0.0422(5) Uani 1 1 d . . . . .
C17 C 0.73883(14) 0.3805(3) 0.65543(10) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.22902(15) 0.2940(3) 0.56920(10) 0.0487(5) Uani 1 1 d . . . . .
C12 C 0.26735(15) 0.6248(3) 0.64715(10) 0.0475(5) Uani 1 1 d . . . . .
C19 C 0.68406(15) 0.2107(3) 0.68021(10) 0.0526(6) Uani 1 1 d . . . . .
H14 H 0.7191 0.0883 0.7055 0.063 Uiso 1 1 calc R U . . .
C7 C 0.19277(15) 0.4792(4) 0.60687(10) 0.0498(5) Uani 1 1 d . . . . .
C15 C 0.57929(15) 0.5725(3) 0.60623(10) 0.0502(5) Uani 1 1 d . . . . .
H9 H 0.5446 0.6959 0.5812 0.060 Uiso 1 1 calc R U . . .
C2 C 0.37542(17) 0.0854(3) 0.54243(10) 0.0532(6) Uani 1 1 d . . . . .
H1 H 0.4472 0.0679 0.5473 0.064 Uiso 1 1 calc R U . . .
C16 C 0.68660(15) 0.5611(3) 0.61791(10) 0.0519(6) Uani 1 1 d . . . . .
H10 H 0.7237 0.6751 0.6005 0.062 Uiso 1 1 calc R U . . .
C20 C 0.57605(16) 0.2233(3) 0.66722(10) 0.0534(6) Uani 1 1 d . . . . .
H15 H 0.5390 0.1065 0.6834 0.064 Uiso 1 1 calc R U . . .
C11 C 0.23559(16) 0.8043(4) 0.68516(11) 0.0584(6) Uani 1 1 d . . . . .
H8 H 0.2854 0.9009 0.7117 0.070 Uiso 1 1 calc R U . . .
C5 C 0.16237(18) 0.1384(4) 0.52604(12) 0.0646(6) Uani 1 1 d . . . . .
H4 H 0.0903 0.1552 0.5195 0.078 Uiso 1 1 calc R U . . .
C3 C 0.30922(19) -0.0648(4) 0.50174(11) 0.0636(6) Uani 1 1 d . . . . .
H2 H 0.3356 -0.1853 0.4796 0.076 Uiso 1 1 calc R U . . .
C8 C 0.08709(17) 0.5214(4) 0.60654(12) 0.0692(7) Uani 1 1 d . . . . .
H5 H 0.0360 0.4277 0.5801 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2022(2) -0.0371(4) 0.49355(11) 0.0693(7) Uani 1 1 d . . . . .
H3 H 0.1570 -0.1393 0.4656 0.083 Uiso 1 1 calc R U . . .
C10 C 0.13244(18) 0.8393(4) 0.68377(13) 0.0707(7) Uani 1 1 d . . . . .
H7 H 0.1121 0.9588 0.7094 0.085 Uiso 1 1 calc R U . . .
C18 C 0.90373(17) 0.2086(4) 0.70451(13) 0.0776(8) Uani 1 1 d . . . . .
H12 H 0.8870 0.2036 0.7497 0.116 Uiso 1 1 calc R U . . .
H11 H 0.9770 0.2386 0.7096 0.116 Uiso 1 1 calc R U . . .
H13 H 0.8867 0.0635 0.6815 0.116 Uiso 1 1 calc R U . . .
C9 C 0.05810(18) 0.6966(5) 0.64415(14) 0.0770(8) Uani 1 1 d . . . . .
H6 H -0.0123 0.7207 0.6432 0.092 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 C17 1.370(2) . ?
O1 C18 1.414(2) . ?
N1 C13 1.308(2) . ?
N1 C12 1.385(2) . ?
C13 C1 1.440(3) . ?
C13 C14 1.489(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.405(3) . ?
C14 C20 1.379(3) . ?
C14 C15 1.379(3) . ?
C17 C19 1.370(3) . ?
C17 C16 1.376(3) . ?
C6 C5 1.406(3) . ?
C6 C7 1.444(3) . ?
C12 C11 1.398(3) . ?
C12 C7 1.400(3) . ?
C19 C20 1.385(3) . ?
C19 H14 0.9300 . ?
C7 C8 1.405(3) . ?
C15 C16 1.376(3) . ?
C15 H9 0.9300 . ?
C2 C3 1.361(3) . ?
C2 H1 0.9300 . ?
C16 H10 0.9300 . ?
C20 H15 0.9300 . ?
C11 C10 1.362(3) . ?
C11 H8 0.9300 . ?
C5 C4 1.366(3) . ?
C5 H4 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H2 0.9300 . ?
C8 C9 1.360(3) . ?
C8 H5 0.9300 . ?
C4 H3 0.9300 . ?
C10 C9 1.383(3) . ?
C10 H7 0.9300 . ?
C18 H12 0.9600 . ?
C18 H11 0.9600 . ?
C18 H13 0.9600 . ?
C9 H6 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
C17 O1 C18 117.91(17) . . ?
C13 N1 C12 118.37(17) . . ?
N1 C13 C1 123.53(17) . . ?
N1 C13 C14 115.34(17) . . ?
C1 C13 C14 121.12(17) . . ?
C2 C1 C6 119.40(18) . . ?
C2 C1 C13 121.81(18) . . ?
C6 C1 C13 118.79(17) . . ?
C20 C14 C15 117.76(18) . . ?
C20 C14 C13 121.56(17) . . ?
C15 C14 C13 120.63(16) . . ?
O1 C17 C19 124.63(18) . . ?
O1 C17 C16 115.28(18) . . ?
C19 C17 C16 120.08(18) . . ?
C1 C6 C5 118.23(19) . . ?
C1 C6 C7 117.86(18) . . ?
C5 C6 C7 123.90(19) . . ?
N1 C12 C11 116.79(18) . . ?
N1 C12 C7 123.18(18) . . ?
C11 C12 C7 120.01(18) . . ?
C17 C19 C20 119.36(18) . . ?
C17 C19 H14 120.3 . . ?
C20 C19 H14 120.3 . . ?
C12 C7 C8 117.6(2) . . ?
C12 C7 C6 118.22(17) . . ?
C8 C7 C6 124.2(2) . . ?
C16 C15 C14 121.38(18) . . ?
C16 C15 H9 119.3 . . ?
C14 C15 H9 119.3 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H1 119.4 . . ?
C1 C2 H1 119.4 . . ?
C15 C16 C17 119.82(19) . . ?
C15 C16 H10 120.1 . . ?
C17 C16 H10 120.1 . . ?
C14 C20 C19 121.58(19) . . ?
C14 C20 H15 119.2 . . ?
C19 C20 H15 119.2 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H8 119.7 . . ?
C12 C11 H8 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H4 119.6 . . ?
C6 C5 H4 119.6 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H2 120.2 . . ?
C4 C3 H2 120.2 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H5 119.3 . . ?
C7 C8 H5 119.3 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H3 119.6 . . ?
C3 C4 H3 119.6 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H7 120.1 . . ?
C9 C10 H7 120.1 . . ?
O1 C18 H12 109.5 . . ?
O1 C18 H11 109.5 . . ?
H12 C18 H11 109.5 . . ?
O1 C18 H13 109.5 . . ?
H12 C18 H13 109.5 . . ?
H11 C18 H13 109.5 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H6 119.7 . . ?
C10 C9 H6 119.7 . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
