# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mo_20170503fj_2_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1821530'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 N2'
_chemical_formula_weight         344.40

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'

_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                   11.544(4)
_cell_length_b                   11.822(4)
_cell_length_c                   16.267(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.419(5)
_cell_angle_gamma                90
_cell_volume                     2118.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3024
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      23.62
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            15142
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.166
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3715
_reflns_number_gt                2492
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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)+(0.1233P)²+0.4625P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.2215
_refine_ls_wR_factor_gt          0.1864
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.1236(3) 0.5077(2) 0.22667(17) 0.0594(7) Uani 1 1 d . . . . .
H1 H 0.1768 0.5564 0.2111 0.071 Uiso 1 1 calc R U . . .
C2 C 0.0013(3) 0.5198(3) 0.1934(2) 0.0725(9) Uani 1 1 d . . . . .
H2 H -0.0296 0.5771 0.1537 0.087 Uiso 1 1 calc R U . . .
C3 C -0.0792(3) 0.4476(3) 0.2178(2) 0.0776(9) Uani 1 1 d . . . . .
H3 H -0.1624 0.4587 0.1949 0.093 Uiso 1 1 calc R U . . .
C4 C -0.0368(3) 0.3607(3) 0.27509(19) 0.0662(8) Uani 1 1 d . . . . .
H4 H -0.0906 0.3127 0.2907 0.079 Uiso 1 1 calc R U . . .
C5 C 0.0872(3) 0.3459(2) 0.30907(16) 0.0548(7) Uani 1 1 d . . . . .
C6 C 0.1665(2) 0.4196(2) 0.28506(15) 0.0520(7) Uani 1 1 d . . . . .
C7 C 0.1627(2) 0.2642(2) 0.36791(16) 0.0548(7) Uani 1 1 d . . . . .
C8 C 0.1389(3) 0.1726(3) 0.41402(19) 0.0673(8) Uani 1 1 d . . . . .
H8 H 0.0594 0.1513 0.4086 0.081 Uiso 1 1 calc R U . . .
C9 C 0.2335(3) 0.1147(3) 0.4670(2) 0.0762(9) Uani 1 1 d . . . . .
H9 H 0.2177 0.0526 0.4971 0.091 Uiso 1 1 calc R U . . .
C10 C 0.3540(3) 0.1456(3) 0.47755(19) 0.0697(8) Uani 1 1 d . . . . .
H10 H 0.4170 0.1060 0.5159 0.084 Uiso 1 1 calc R U . . .
C11 C 0.3795(3) 0.2351(2) 0.43100(17) 0.0609(7) Uani 1 1 d . . . . .
H11 H 0.4592 0.2554 0.4362 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2834(2) 0.2932(2) 0.37670(15) 0.0518(7) Uani 1 1 d . . . . .
C13 C 0.3912(2) 0.4371(2) 0.31188(15) 0.0526(6) Uani 1 1 d . . . . .
C14 C 0.4496(3) 0.3779(3) 0.26339(18) 0.0672(8) Uani 1 1 d . . . . .
H14 H 0.4232 0.3058 0.2435 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5477(3) 0.4256(3) 0.2442(2) 0.0792(10) Uani 1 1 d . . . . .
H15 H 0.5878 0.3855 0.2116 0.095 Uiso 1 1 calc R U . . .
C16 C 0.5859(3) 0.5322(3) 0.2732(2) 0.0789(10) Uani 1 1 d . . . . .
H16 H 0.6513 0.5648 0.2597 0.095 Uiso 1 1 calc R U . . .
C17 C 0.5270(3) 0.5915(3) 0.32281(18) 0.0648(8) Uani 1 1 d . . . . .
H17 H 0.5536 0.6636 0.3425 0.078 Uiso 1 1 calc R U . . .
C18 C 0.4291(2) 0.5445(2) 0.34323(15) 0.0501(6) Uani 1 1 d . . . . .
C19 C 0.3700(2) 0.6096(2) 0.39801(15) 0.0480(6) Uani 1 1 d . . . . .
C20 C 0.3453(2) 0.5605(2) 0.46896(15) 0.0510(6) Uani 1 1 d . . . . .
H20 H 0.3609 0.4840 0.4804 0.061 Uiso 1 1 calc R U . . .
C21 C 0.2985(2) 0.6239(2) 0.52179(16) 0.0545(7) Uani 1 1 d . . . . .
H21 H 0.2830 0.5906 0.5692 0.065 Uiso 1 1 calc R U . . .
C22 C 0.2741(2) 0.7385(2) 0.50449(17) 0.0560(7) Uani 1 1 d . . . . .
C23 C 0.2972(3) 0.7878(2) 0.43409(18) 0.0589(7) Uani 1 1 d . . . . .
H23 H 0.2803 0.8640 0.4220 0.071 Uiso 1 1 calc R U . . .
C24 C 0.3453(3) 0.7237(2) 0.38235(16) 0.0563(7) Uani 1 1 d . . . . .
H24 H 0.3620 0.7575 0.3355 0.068 Uiso 1 1 calc R U . . .
C25 C 0.2247(3) 0.8039(3) 0.5610(2) 0.0663(8) Uani 1 1 d . . . . .
N1 N 0.28557(19) 0.38765(18) 0.32606(12) 0.0503(6) Uani 1 1 d . . . . .
N2 N 0.1875(3) 0.8565(3) 0.6058(2) 0.0914(9) Uani 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
C1 C2 1.360(4) . ?
C1 C6 1.397(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.404(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(4) . ?
C5 C7 1.452(4) . ?
C6 N1 1.389(3) . ?
C7 C8 1.391(4) . ?
C7 C12 1.400(4) . ?
C8 C9 1.356(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.392(3) . ?
C13 C14 1.373(4) . ?
C13 C18 1.389(4) . ?
C13 N1 1.432(3) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.490(3) . ?
C19 C24 1.386(4) . ?
C19 C20 1.395(3) . ?
C20 C21 1.367(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(4) . ?
C22 C25 1.443(4) . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.136(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
C2 C1 C6 117.6(3) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 C7 133.8(3) . . ?
C6 C5 C7 106.5(2) . . ?
N1 C6 C1 128.9(3) . . ?
N1 C6 C5 109.4(2) . . ?
C1 C6 C5 121.7(3) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 C5 134.2(3) . . ?
C12 C7 C5 106.7(2) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 N1 128.8(3) . . ?
C11 C12 C7 122.0(3) . . ?
N1 C12 C7 109.2(2) . . ?
C14 C13 C18 121.5(3) . . ?
C14 C13 N1 118.2(3) . . ?
C18 C13 N1 120.2(2) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 C19 119.2(3) . . ?
C13 C18 C19 122.8(2) . . ?
C24 C19 C20 118.4(2) . . ?
C24 C19 C18 119.9(2) . . ?
C20 C19 C18 121.6(2) . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 C25 120.9(3) . . ?
C21 C22 C25 119.1(2) . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C19 121.7(2) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
N2 C25 C22 178.8(3) . . ?
C6 N1 C12 108.2(2) . . ?
C6 N1 C13 125.5(2) . . ?
C12 N1 C13 126.1(2) . . ?

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.045




