# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mdpa
_database_code_depnum_ccdc_archive 'CCDC 2040167'
loop_
_audit_author_name
_audit_author_address
'Tianyang Wang'
;Tianjin University
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-03-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        C13H13N
_chemical_formula_moiety         'C13 H13 N'
_chemical_formula_sum            'C13 H13 N'
_chemical_formula_weight         183.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9980(2)
_cell_length_b                   15.4512(2)
_cell_length_c                   7.50250(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2086.38(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18232
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9690
_cell_measurement_theta_min      3.7480
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0080
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            36546
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.223
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  19.00   1.00    1.98    --   34.00 100.00 -32.70   26
  2  ω     -7.00  19.00   1.00    1.98    --   34.00 100.00  87.35   26
  3  ω   -116.00 -17.00   1.00    1.98    --  -41.12 -37.00-150.00   99
  4  ω    -65.00  33.00   1.00    1.98    --  -41.12  37.00  30.00   98
  5  ω   -113.00 -13.00   1.00    1.98    --  -41.12 -57.00  60.00  100
  6  ω    -69.00  32.00   1.00    1.98    --  -41.12  57.00-150.00  101
  7  ω     23.00  97.00   1.00    1.98    --   41.12-125.00 120.00   74
  8  ω    -31.00  69.00   1.00    1.98    --   41.12 -57.00-150.00  100
  9  ω      5.00  33.00   1.00    1.98    --   42.00  89.00  27.67   28
 10  ω      7.00  35.00   1.00    1.98    --   42.00  86.00-131.74   28
 11  ω     12.00  40.00   1.00    1.98    --   46.00  83.00 -65.67   28
 12  ω     12.00  40.00   1.00    1.98    --   46.00  83.00 133.94   28
 13  ω     25.00 134.00   1.00    1.98    --   58.00  77.00  19.03  109
 14  ω     26.00 134.00   1.00    1.98    --   58.00  76.00 -41.76  108
 15  ω     30.00 137.00   1.00    1.98    --   62.00  75.00  70.66  107
 16  ω     30.00 137.00   1.00    1.98    --   62.00  75.00 -93.76  107
 17  ω     30.00 137.00   1.00    1.98    --   62.00  75.00 -18.32  107
 18  ω     34.00 142.00   1.00    1.98    --   66.00  76.00 153.63  108
 19  ω     34.00 142.00   1.00    1.98    --   66.00  76.00 115.19  108
 20  ω     34.00 141.00   1.00    1.98    --   66.00  75.00  96.74  107
 21  ω     33.00 142.00   1.00    1.98    --   66.00  77.00-130.10  109
 22  ω     37.00 144.00   1.00    1.98    --   70.00  77.00-168.34  107
 23  ω     53.00 137.00   1.00    7.92    --  105.32 -77.00 -90.00   84
 24  ω     73.00 163.00   1.00    7.92    --  105.32  77.00 -60.00   90
 25  ω     33.00 117.00   1.00    7.92    --  105.32-125.00-180.00   84
 26  ω    108.00 177.00   1.00    7.92    --  105.32  77.00-120.00   69
 27  ω     29.00 125.00   1.00    7.92    --  105.32 -77.00-180.00   96
 28  ω     73.00 103.00   1.00    7.92    --  105.32  77.00-120.00   30
 29  ω     76.00 103.00   1.00    7.92    --  105.32  61.00 -30.00   27
 30  ω     73.00 171.00   1.00    7.92    --  105.32  77.00   0.00   98
 31  ω     73.00 170.00   1.00    7.92    --  105.32  77.00 120.00   97
 32  ω     76.00 102.00   1.00    7.92    --  105.32  61.00 -90.00   26
 33  ω     77.00 137.00   1.00    7.92    --  105.32  61.00 -60.00   60
 34  ω     73.00 163.00   1.00    7.92    --  105.32  77.00  60.00   90
 35  ω     77.00 151.00   1.00    7.92    --  105.32  61.00   0.00   74
 36  ω     73.00 168.00   1.00    7.92    --  105.32  77.00  30.00   95
 37  ω     74.00 162.00   1.00    7.92    --  105.32  77.00 150.00   88
 38  ω    112.00 168.00   1.00    7.92    --  105.32  77.00-180.00   56
 39  ω     73.00  99.00   1.00    7.92    --  105.32  77.00-180.00   26
 40  ω     73.00 142.00   1.00    7.92    --  105.32  77.00-150.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0834410000
_diffrn_orient_matrix_UB_12      0.0204388000
_diffrn_orient_matrix_UB_13      0.0178190000
_diffrn_orient_matrix_UB_21      -0.0169879000
_diffrn_orient_matrix_UB_22      0.0973959000
_diffrn_orient_matrix_UB_23      -0.0164292000
_diffrn_orient_matrix_UB_31      -0.0086510000
_diffrn_orient_matrix_UB_32      0.0060801000
_diffrn_orient_matrix_UB_33      0.2039211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1853
_reflns_number_total             2076
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0861P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1590
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N(H)
2.b Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C2AA(H2AA), C4AA(H4AA), C5AA(H5AA), C6AA(H6AA), C8AA(H8AA),
 C9AA(H9AA), C0BA(H0BA), C1BA(H1BA)
2.c Idealised Me refined as rotating group:
 C(Ha,Hb,Hc)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N N 0.68919(7) 0.97097(10) 0.03501(18) 0.0667(4) Uani 1 1 d . . . . .
H H 0.7325 0.9493 0.0531 0.080 Uiso 1 1 d R . . . .
C0AA C 0.64760(8) 0.91283(9) -0.06606(18) 0.0519(4) Uani 1 1 d . . . . .
C1AA C 0.60317(8) 1.00978(10) 0.4762(2) 0.0560(4) Uani 1 1 d . . . . .
H1AA H 0.5748 0.9798 0.5595 0.067 Uiso 1 1 calc R . . . .
C2AA C 0.68345(10) 0.85814(11) -0.1862(2) 0.0652(4) Uani 1 1 d . . . . .
H2AA H 0.7350 0.8584 -0.1930 0.078 Uiso 1 1 calc R . . . .
C3AA C 0.66563(7) 1.01162(10) 0.19247(19) 0.0519(4) Uani 1 1 d . . . . .
C4AA C 0.68578(8) 1.09675(11) 0.2265(2) 0.0610(4) Uani 1 1 d . . . . .
H4AA H 0.7137 1.1271 0.1430 0.073 Uiso 1 1 calc R . . . .
C5AA C 0.62443(8) 0.96819(9) 0.3216(2) 0.0540(4) Uani 1 1 d . . . . .
H5AA H 0.6111 0.9107 0.3035 0.065 Uiso 1 1 calc R . . . .
C6AA C 0.57032(8) 0.90981(9) -0.0570(2) 0.0551(4) Uani 1 1 d . . . . .
H6AA H 0.5452 0.9451 0.0232 0.066 Uiso 1 1 calc R . . . .
C7AA C 0.62279(8) 1.09467(10) 0.5110(2) 0.0586(4) Uani 1 1 d . . . . .
C8AA C 0.53093(10) 0.85472(11) -0.1664(2) 0.0683(5) Uani 1 1 d . . . . .
H8AA H 0.4793 0.8535 -0.1595 0.082 Uiso 1 1 calc R . . . .
C9AA C 0.66484(8) 1.13678(10) 0.3833(2) 0.0629(4) Uani 1 1 d . . . . .
H9AA H 0.6794 1.1937 0.4035 0.076 Uiso 1 1 calc R . . . .
C0BA C 0.64330(13) 0.80394(11) -0.2945(3) 0.0792(5) Uani 1 1 d . . . . .
H0BA H 0.6680 0.7684 -0.3750 0.095 Uiso 1 1 calc R . . . .
C C 0.59931(12) 1.13827(14) 0.6814(3) 0.0880(6) Uani 1 1 d . . . . .
HA H 0.5474 1.1280 0.7017 0.132 Uiso 1 1 calc GR . . . .
HB H 0.6080 1.1994 0.6723 0.132 Uiso 1 1 calc GR . . . .
HC H 0.6275 1.1152 0.7791 0.132 Uiso 1 1 calc GR . . . .
C1BA C 0.56670(13) 0.80153(12) -0.2854(3) 0.0806(6) Uani 1 1 d . . . . .
H1BA H 0.5398 0.7645 -0.3587 0.097 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
N C0AA 1.394(2) . ?
N C3AA 1.4035(19) . ?
C0AA C2AA 1.394(2) . ?
C0AA C6AA 1.393(2) . ?
C1AA C5AA 1.380(2) . ?
C1AA C7AA 1.383(2) . ?
C2AA C0BA 1.373(3) . ?
C3AA C4AA 1.388(2) . ?
C3AA C5AA 1.392(2) . ?
C4AA C9AA 1.381(2) . ?
C6AA C8AA 1.379(2) . ?
C7AA C9AA 1.383(2) . ?
C7AA C 1.506(2) . ?
C8AA C1BA 1.374(3) . ?
C0BA C1BA 1.381(3) . ?

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
C0AA N C3AA 125.75(12) . . ?
N C0AA C2AA 119.60(14) . . ?
C6AA C0AA N 122.09(13) . . ?
C6AA C0AA C2AA 118.25(14) . . ?
C5AA C1AA C7AA 121.96(15) . . ?
C0BA C2AA C0AA 120.59(16) . . ?
C4AA C3AA N 120.01(14) . . ?
C4AA C3AA C5AA 117.90(14) . . ?
C5AA C3AA N 122.05(14) . . ?
C9AA C4AA C3AA 120.64(14) . . ?
C1AA C5AA C3AA 120.52(14) . . ?
C8AA C6AA C0AA 120.34(14) . . ?
C1AA C7AA C9AA 117.06(14) . . ?
C1AA C7AA C 120.85(17) . . ?
C9AA C7AA C 122.09(16) . . ?
C1BA C8AA C6AA 121.01(16) . . ?
C4AA C9AA C7AA 121.90(15) . . ?
C2AA C0BA C1BA 120.86(16) . . ?
C8AA C1BA C0BA 118.94(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.544
