# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mmm197_NH_0msi
_database_code_depnum_ccdc_archive 'CCDC 1522122'
_audit_update_record             
;
2016-12-11 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.8734(9)
_cell_length_b                   5.0259(3)
_cell_length_c                   9.8407(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.4397(19)
_cell_angle_gamma                90
_cell_volume                     718.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'w-scans and phi-scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            19237
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         28.736
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1860
_reflns_number_gt                1628
_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 2014.1-1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 NH free with DFIX
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1860
_refine_ls_number_parameters     113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
N1 N 0.15296(6) 0.26032(18) 0.72656(9) 0.0159(2) Uani 1 1 d D . . . .
H01 H 0.1285(10) 0.396(3) 0.7610(15) 0.027(4) Uiso 1 1 d D . . . .
C1 C 0.24534(7) 0.1886(2) 0.76116(10) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.31650(8) 0.2969(2) 0.86177(11) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.3062 0.4430 0.9178 0.023 Uiso 1 1 calc R U . . .
C3 C 0.40292(8) 0.1827(2) 0.87667(11) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.4527 0.2518 0.9446 0.026 Uiso 1 1 calc R U . . .
C4 C 0.41879(8) -0.0326(2) 0.79389(12) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.4789 -0.1059 0.8066 0.026 Uiso 1 1 calc R U . . .
C5 C 0.34790(7) -0.1396(2) 0.69383(11) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.3589 -0.2850 0.6379 0.023 Uiso 1 1 calc R U . . .
C6 C 0.25958(7) -0.0284(2) 0.67695(10) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.17145(7) -0.0846(2) 0.58630(10) 0.0150(2) Uani 1 1 d . . . . .
C8 C 0.14231(7) -0.2748(2) 0.48020(11) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.1849 -0.3981 0.4567 0.020 Uiso 1 1 calc R U . . .
C9 C 0.05152(7) -0.2791(2) 0.41150(10) 0.0158(2) Uani 1 1 d . . . . .
H9 H 0.0318 -0.4051 0.3392 0.019 Uiso 1 1 calc R U . . .
C10 C 0.01368(7) 0.09768(19) 0.55320(10) 0.0140(2) Uani 1 1 d . . . . .
C11 C 0.10826(7) 0.0975(2) 0.62037(10) 0.0145(2) 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
N1 C11 1.3800(13) . ?
N1 C1 1.3900(13) . ?
C1 C2 1.3947(15) . ?
C1 C6 1.4131(15) . ?
C2 C3 1.3865(16) . ?
C3 C4 1.4045(17) . ?
C4 C5 1.3868(16) . ?
C5 C6 1.4041(15) . ?
C6 C7 1.4457(14) . ?
C7 C11 1.4032(14) . ?
C7 C8 1.4131(14) . ?
C8 C9 1.3739(15) . ?
C9 C10 1.4276(14) 3_556 ?
C10 C11 1.4196(14) . ?
C10 C9 1.4275(14) 3_556 ?
C10 C10 1.4291(19) 3_556 ?

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
C11 N1 C1 108.74(9) . . ?
N1 C1 C2 129.17(10) . . ?
N1 C1 C6 108.75(9) . . ?
C2 C1 C6 122.06(10) . . ?
C3 C2 C1 117.25(11) . . ?
C2 C3 C4 121.70(10) . . ?
C5 C4 C3 120.90(10) . . ?
C4 C5 C6 118.58(10) . . ?
C5 C6 C1 119.50(10) . . ?
C5 C6 C7 134.10(10) . . ?
C1 C6 C7 106.40(9) . . ?
C11 C7 C8 120.20(9) . . ?
C11 C7 C6 106.86(9) . . ?
C8 C7 C6 132.94(10) . . ?
C9 C8 C7 119.14(9) . . ?
C8 C9 C10 121.15(9) . 3_556 ?
C11 C10 C9 122.96(9) . 3_556 ?
C11 C10 C10 115.97(11) . 3_556 ?
C9 C10 C10 121.06(12) 3_556 3_556 ?
N1 C11 C7 109.24(9) . . ?
N1 C11 C10 128.29(9) . . ?
C7 C11 C10 122.46(9) . . ?

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
C11 N1 C1 C2 179.96(10) . . . . ?
C11 N1 C1 C6 -1.15(11) . . . . ?
N1 C1 C2 C3 178.70(10) . . . . ?
C6 C1 C2 C3 -0.06(16) . . . . ?
C1 C2 C3 C4 0.25(17) . . . . ?
C2 C3 C4 C5 -0.18(18) . . . . ?
C3 C4 C5 C6 -0.09(16) . . . . ?
C4 C5 C6 C1 0.27(16) . . . . ?
C4 C5 C6 C7 179.96(11) . . . . ?
N1 C1 C6 C5 -179.19(9) . . . . ?
C2 C1 C6 C5 -0.20(16) . . . . ?
N1 C1 C6 C7 1.05(11) . . . . ?
C2 C1 C6 C7 -179.97(9) . . . . ?
C5 C6 C7 C11 179.72(11) . . . . ?
C1 C6 C7 C11 -0.56(11) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C1 C6 C7 C8 179.56(11) . . . . ?
C11 C7 C8 C9 -0.18(15) . . . . ?
C6 C7 C8 C9 179.69(10) . . . . ?
C7 C8 C9 C10 -0.85(15) . . . 3_556 ?
C1 N1 C11 C7 0.79(11) . . . . ?
C1 N1 C11 C10 179.48(9) . . . . ?
C8 C7 C11 N1 179.77(9) . . . . ?
C6 C7 C11 N1 -0.13(11) . . . . ?
C8 C7 C11 C10 0.99(15) . . . . ?
C6 C7 C11 C10 -178.91(9) . . . . ?
C9 C10 C11 N1 0.43(16) 3_556 . . . ?
C10 C10 C11 N1 -179.25(11) 3_556 . . . ?
C9 C10 C11 C7 178.96(9) 3_556 . . . ?
C10 C10 C11 C7 -0.72(16) 3_556 . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



