# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Esser_JW_547_0m
_database_code_depnum_ccdc_archive 'CCDC 2001350'
loop_
_audit_author_name
_audit_author_address
'Jan Stephan Woessner'
;Albert Ludwigs University of Freiburg
Germany
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-05-12 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V58 by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C12 H11 N2'
_chemical_formula_moiety         C24H22N4
_chemical_formula_weight         183.23
_chemical_melting_point          ?
_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                   9.4727(5)
_cell_length_b                   10.4994(6)
_cell_length_c                   9.5491(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.527(3)
_cell_angle_gamma                90
_cell_volume                     930.58(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.916
_cell_measurement_theta_max      25.054
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_recrystallization_method 
'Recrystallised from a mixture of dimethylformamide and methanol by solventlayering.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          ?
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 HPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_measurement_specimen_adhesive ?
_diffrn_reflns_number            27035
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_theta_min         2.916
_diffrn_reflns_theta_max         25.137
_diffrn_reflns_theta_full        25.137
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1641
_reflns_number_gt                1538
_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 BIS V6.2.12/2019-08-12'
_computing_cell_refinement       'SAINT V8.40A'
_computing_data_reduction        'SAINT V8.40A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.443
_refine_ls_restrained_S_all      1.443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.50318(8) 0.75158(8) 0.36352(9) 0.0160(3) Uani 1 1 d . . . . .
N2 N 0.47023(8) 0.95366(8) 0.44864(8) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.00624(11) 0.55919(11) 0.29593(13) 0.0283(4) Uani 1 1 d . . . . .
H1 H -0.076104 0.512182 0.308247 0.034 Uiso 1 1 calc R U . . .
C2 C 0.08585(11) 0.51967(11) 0.19778(12) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.056967 0.446301 0.141057 0.031 Uiso 1 1 calc R U . . .
C3 C 0.20810(10) 0.58659(10) 0.18138(10) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.264033 0.557210 0.115667 0.023 Uiso 1 1 calc R U . . .
C4 C 0.24885(10) 0.69612(9) 0.26054(10) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.38053(10) 0.77009(10) 0.24288(10) 0.0177(3) Uani 1 1 d . . . . .
H5A H 0.409357 0.743118 0.153283 0.021 Uiso 1 1 calc R U . . .
H5B H 0.356218 0.861829 0.234251 0.021 Uiso 1 1 calc R U . . .
C6 C 0.54908(10) 0.85097(9) 0.45954(10) 0.0149(3) Uani 1 1 d . . . . .
C7 C 0.16666(11) 0.73644(10) 0.35805(11) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.192900 0.811636 0.412362 0.026 Uiso 1 1 calc R U . . .
C8 C 0.04669(12) 0.66740(12) 0.37631(12) 0.0286(4) Uani 1 1 d . . . . .
H8 H -0.007765 0.694627 0.444253 0.034 Uiso 1 1 calc R U . . .
C9 C 0.67999(10) 0.82566(10) 0.56276(11) 0.0179(3) Uani 1 1 d . . . . .
H9 H 0.722597 0.892224 0.624363 0.022 Uiso 1 1 calc R U . . .
C10 C 0.74312(11) 0.71003(10) 0.57379(11) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.827821 0.695888 0.644228 0.025 Uiso 1 1 calc R U . . .
C11 C 0.68420(11) 0.60894(10) 0.48102(11) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.725326 0.526104 0.491272 0.026 Uiso 1 1 calc R U . . .
C12 C 0.56817(10) 0.63465(10) 0.37819(10) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.529906 0.568933 0.313227 0.023 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0169(5) 0.0146(5) 0.0166(5) -0.0003(3) 0.0035(4) 0.0008(3)
N2 0.0175(5) 0.0155(5) 0.0161(5) -0.0015(3) 0.0033(4) -0.0003(3)
C1 0.0158(5) 0.0337(7) 0.0328(7) 0.0149(5) -0.0011(5) -0.0024(4)
C2 0.0244(6) 0.0222(6) 0.0254(6) 0.0052(4) -0.0059(5) -0.0037(4)
C3 0.0224(6) 0.0179(6) 0.0165(6) 0.0016(4) 0.0002(4) 0.0012(4)
C4 0.0162(6) 0.0169(6) 0.0143(6) 0.0037(4) -0.0001(4) 0.0036(4)
C5 0.0195(6) 0.0175(6) 0.0152(5) -0.0005(4) 0.0014(4) -0.0004(4)
C6 0.0157(5) 0.0144(6) 0.0158(6) 0.0012(4) 0.0059(4) -0.0019(4)
C7 0.0210(6) 0.0228(6) 0.0211(6) 0.0007(4) 0.0035(4) 0.0057(4)
C8 0.0203(6) 0.0370(8) 0.0300(7) 0.0089(5) 0.0090(5) 0.0077(4)
C9 0.0172(6) 0.0192(6) 0.0175(6) -0.0007(4) 0.0037(4) -0.0007(4)
C10 0.0169(6) 0.0230(6) 0.0217(6) 0.0033(4) 0.0027(4) 0.0032(4)
C11 0.0212(6) 0.0177(6) 0.0260(6) 0.0016(4) 0.0056(4) 0.0042(4)
C12 0.0218(6) 0.0146(6) 0.0217(6) -0.0016(4) 0.0073(5) 0.0000(4)

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 C12 1.3679(13) . ?
N1 C6 1.3999(12) . ?
N1 C5 1.4764(11) . ?
N2 C6 1.3038(13) . ?
N2 N2 1.4163(15) 3_676 ?
C1 C2 1.3790(18) . ?
C1 C8 1.3818(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3898(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3879(14) . ?
C3 H3 0.9500 . ?
C4 C7 1.3937(14) . ?
C4 C5 1.5071(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C9 1.4462(14) . ?
C7 C8 1.3879(16) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.3481(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4232(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.3467(14) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C12 N1 C6 121.83(8) . . ?
C12 N1 C5 117.77(8) . . ?
C6 N1 C5 120.39(8) . . ?
C6 N2 N2 111.74(9) . 3_676 ?
C2 C1 C8 119.75(10) . . ?
C2 C1 H1 120.1 . . ?
C8 C1 H1 120.1 . . ?
C1 C2 C3 120.37(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.32(10) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C7 118.94(9) . . ?
C3 C4 C5 120.82(9) . . ?
C7 C4 C5 120.24(9) . . ?
N1 C5 C4 112.63(8) . . ?
N1 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N2 C6 N1 117.79(9) . . ?
N2 C6 C9 127.29(9) . . ?
N1 C6 C9 114.91(9) . . ?
C8 C7 C4 120.40(10) . . ?
C8 C7 H7 119.8 . . ?
C4 C7 H7 119.8 . . ?
C1 C8 C7 120.19(10) . . ?
C1 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C6 121.69(10) . . ?
C10 C9 H9 119.2 . . ?
C6 C9 H9 119.2 . . ?
C9 C10 C11 120.68(9) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 117.76(9) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 N1 122.66(9) . . ?
C11 C12 H12 118.7 . . ?
N1 C12 H12 118.7 . . ?

_shelx_res_file                  
;
TITL mo_Esser_JW_547_0m_a.res in P2(1)/c
    mo_Esser_JW_547_0m.res
    created by SHELXL-2018/3 at 10:29:30 on 06-May-2020
CELL 0.71073 9.4727 10.4994 9.5491 90.000 101.527 90.000
ZERR 4.00 0.0005 0.0006 0.0006 0.000 0.003 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N
UNIT 48 44 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173.150
ACTA
L.S. 4
FMAP 2
PLAN -1 0 0.00
BOND $H
WGHT    0.100000
FVAR       1.74488
N1    3    0.503182    0.751577    0.363517    11.00000    0.01694    0.01462 =
         0.01665   -0.00031    0.00354    0.00076
N2    3    0.470233    0.953658    0.448644    11.00000    0.01746    0.01547 =
         0.01613   -0.00147    0.00332   -0.00035
C1    1    0.006242    0.559188    0.295935    11.00000    0.01577    0.03366 =
         0.03283    0.01494   -0.00115   -0.00238
AFIX  43
H1    2   -0.076104    0.512182    0.308247    11.00000   -1.20000
AFIX   0
C2    1    0.085850    0.519674    0.197781    11.00000    0.02436    0.02218 =
         0.02543    0.00515   -0.00592   -0.00368
AFIX  43
H2    2    0.056967    0.446301    0.141057    11.00000   -1.20000
AFIX   0
C3    1    0.208096    0.586587    0.181377    11.00000    0.02238    0.01795 =
         0.01655    0.00157    0.00023    0.00118
AFIX  43
H3    2    0.264033    0.557210    0.115667    11.00000   -1.20000
AFIX   0
C4    1    0.248849    0.696122    0.260535    11.00000    0.01621    0.01688 =
         0.01429    0.00373   -0.00013    0.00365
C5    1    0.380529    0.770085    0.242879    11.00000    0.01952    0.01753 =
         0.01521   -0.00050    0.00145   -0.00044
AFIX  23
H5A   2    0.409357    0.743118    0.153283    11.00000   -1.20000
H5B   2    0.356218    0.861829    0.234251    11.00000   -1.20000
AFIX   0
C6    1    0.549079    0.850974    0.459541    11.00000    0.01565    0.01443 =
         0.01584    0.00120    0.00595   -0.00191
C7    1    0.166656    0.736443    0.358054    11.00000    0.02100    0.02281 =
         0.02109    0.00069    0.00346    0.00571
AFIX  43
H7    2    0.192900    0.811636    0.412362    11.00000   -1.20000
AFIX   0
C8    1    0.046691    0.667404    0.376309    11.00000    0.02032    0.03699 =
         0.03005    0.00886    0.00898    0.00766
AFIX  43
H8    2   -0.007765    0.694627    0.444253    11.00000   -1.20000
AFIX   0
C9    1    0.679992    0.825661    0.562756    11.00000    0.01716    0.01922 =
         0.01748   -0.00067    0.00369   -0.00072
AFIX  43
H9    2    0.722597    0.892224    0.624363    11.00000   -1.20000
AFIX   0
C10   1    0.743123    0.710033    0.573792    11.00000    0.01690    0.02298 =
         0.02169    0.00328    0.00270    0.00318
AFIX  43
H10   2    0.827821    0.695888    0.644228    11.00000   -1.20000
AFIX   0
C11   1    0.684197    0.608936    0.481015    11.00000    0.02119    0.01769 =
         0.02605    0.00157    0.00559    0.00424
AFIX  43
H11   2    0.725326    0.526104    0.491272    11.00000   -1.20000
AFIX   0
C12   1    0.568169    0.634652    0.378194    11.00000    0.02176    0.01456 =
         0.02169   -0.00163    0.00725   -0.00004
AFIX  43
H12   2    0.529906    0.568933    0.313227    11.00000   -1.20000
REM <hkl>
REM C:\frames\guest\pa2\work\mo_Esser_JW_547_0m.hkl
REM </hkl>
AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  mo_Esser_JW_547_0m_a.res in P2(1)/c
REM wR2 = 0.152033, GooF = S = 1.44336, Restrained GooF = 1.44336 for all data
REM R1 = 0.032561 for 1538 Fo > 4sig(Fo) and 0.034349 for all 1641 data
REM 127 parameters refined using 0 restraints

END

WGHT      0.0459      0.2770

REM Highest difference peak  0.212,  deepest hole -0.190,  1-sigma level  0.033
Q1    1   0.3128  0.7259  0.2583  11.00000  0.05    0.21
;
_shelx_res_checksum              96017
