# 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_2m-o-4-me
_database_code_depnum_ccdc_archive 'CCDC 2040239'
loop_
_audit_author_name
_audit_author_address
'Tianyang Wang'
;Tianjin University
China
;
_audit_update_record             
;
2021-03-24 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        ?
_chemical_formula_moiety         'C13 H13 N'
_chemical_formula_sum            'C13 H13 N'
_chemical_formula_weight         183.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   18.0056(5)
_cell_length_b                   15.4491(4)
_cell_length_c                   7.5013(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2086.64(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6467
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.1610
_cell_measurement_theta_min      4.9110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68504
_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          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13437
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.236
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      293
_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 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -17.00   1.00    1.28    --  -40.87 -19.00-150.00  104
  2  ω    -88.00 -18.00   1.00    1.28    --  -40.87 125.00 150.00   70
  3  ω    -65.00  28.00   1.00    1.28    --  -40.87  37.00  30.00   93
  4  ω   -109.00 -77.00   1.00    1.28    --  -40.87-147.00  11.00   32
  5  ω     34.00  81.00   1.00    1.28    --   40.87-125.00  90.00   47
  6  ω     48.00 109.00   1.00   10.00    --  105.32-125.00 -60.00   61
  7  ω    147.00 178.00   1.00   10.00    --  105.32 125.00-150.00   31
  8  ω     34.00 134.00   1.00   10.00    --  105.32 -61.00 -90.00  100
  9  ω     96.00 174.00   1.00   10.00    --  105.32 125.00-180.00   78
 10  ω     94.00 136.00   1.00   10.00    --  105.32 125.00-150.00   42
 11  ω     95.00 122.00   1.00   10.00    --  105.32  45.00 -90.00   27
 12  ω    145.00 171.00   1.00   10.00    --  105.32  45.00 -90.00   26
 13  ω     53.00 174.00   1.00   10.00    --  105.32  15.00   0.00  121
 14  ω    121.00 168.00   1.00   10.00    --  105.32 125.00 -30.00   47
 15  ω     92.00 117.00   1.00   10.00    --  105.32-125.00  30.00   25
 16  ω     35.00  60.00   1.00   10.00    --  105.32-125.00  30.00   25
 17  ω     68.00 125.00   1.00   10.00    --  105.32 -30.00 120.00   57
 18  ω     37.00 122.00   1.00   10.00    --  105.32 -45.00  60.00   85
 19  ω    137.00 162.00   1.00   10.00    --  105.32  45.00-180.00   25
 20  ω    151.00 178.00   1.00   10.00    --  105.32 125.00 -90.00   27
;
_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      0.0686684000
_diffrn_orient_matrix_UB_12      0.0591562000
_diffrn_orient_matrix_UB_13      0.0159482000
_diffrn_orient_matrix_UB_21      0.0506776000
_diffrn_orient_matrix_UB_22      -0.0802298000
_diffrn_orient_matrix_UB_23      0.0070834000
_diffrn_orient_matrix_UB_31      0.0071544000
_diffrn_orient_matrix_UB_32      0.0018435000
_diffrn_orient_matrix_UB_33      -0.2044738000
_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                1846
_reflns_number_total             2071
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0751P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1344
_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 Aromatic/amide H refined with riding coordinates:
 N001(H001), C004(H004), C005(H005), C006(H006), C008(H008), C009(H009),
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N001 N 0.31077(6) 0.47043(9) 0.53584(15) 0.0655(3) Uani 1 1 d . . . . .
H001 H 0.2665 0.4817 0.4995 0.079 Uiso 1 1 calc R . . . .
C002 C 0.33436(6) 0.51164(8) 0.69220(16) 0.0507(3) Uani 1 1 d . . . . .
C003 C 0.35244(7) 0.41281(8) 0.43381(15) 0.0507(3) Uani 1 1 d . . . . .
C004 C 0.37562(7) 0.46820(8) 0.82142(16) 0.0522(3) Uani 1 1 d . . . . .
H004 H 0.3890 0.4107 0.8033 0.063 Uiso 1 1 calc R . . . .
C005 C 0.42967(7) 0.40971(8) 0.44299(17) 0.0538(3) Uani 1 1 d . . . . .
H005 H 0.4547 0.4450 0.5234 0.065 Uiso 1 1 calc R . . . .
C006 C 0.39685(7) 0.50975(9) 0.97610(17) 0.0544(3) Uani 1 1 d . . . . .
H006 H 0.4252 0.4798 1.0595 0.065 Uiso 1 1 calc R . . . .
C007 C 0.37721(7) 0.59482(9) 1.01079(18) 0.0568(3) Uani 1 1 d . . . . .
C008 C 0.31413(7) 0.59671(9) 0.72622(18) 0.0592(3) Uani 1 1 d . . . . .
H008 H 0.2862 0.6270 0.6427 0.071 Uiso 1 1 calc R . . . .
C009 C 0.33508(7) 0.63697(8) 0.88326(19) 0.0616(4) Uani 1 1 d . . . . .
H009 H 0.3205 0.6939 0.9036 0.074 Uiso 1 1 calc R . . . .
C00A C 0.31637(8) 0.35820(9) 0.31399(18) 0.0642(4) Uani 1 1 d . . . . .
H00A H 0.2648 0.3585 0.3072 0.077 Uiso 1 1 calc R . . . .
C00B C 0.46922(9) 0.35462(9) 0.33376(19) 0.0665(4) Uani 1 1 d . . . . .
H00B H 0.5208 0.3533 0.3409 0.080 Uiso 1 1 calc R . . . .
C00C C 0.35668(11) 0.30389(10) 0.2057(2) 0.0778(5) Uani 1 1 d . . . . .
H00C H 0.3320 0.2682 0.1253 0.093 Uiso 1 1 calc R . . . .
C00D C 0.43330(11) 0.30164(10) 0.2146(2) 0.0790(5) Uani 1 1 d . . . . .
H00D H 0.4602 0.2647 0.1409 0.095 Uiso 1 1 calc R . . . .
C00E C 0.40083(11) 0.63847(12) 1.1810(2) 0.0861(5) Uani 1 1 d . . . . .
H00E H 0.3762 0.6116 1.2802 0.129 Uiso 1 1 calc GR . . . .
H00F H 0.3877 0.6987 1.1763 0.129 Uiso 1 1 calc GR . . . .
H00G H 0.4536 0.6329 1.1951 0.129 Uiso 1 1 calc GR . . . .


_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
N001 H001 0.8600 . ?
N001 C002 1.4005(16) . ?
N001 C003 1.3933(17) . ?
C002 C004 1.3935(17) . ?
C002 C008 1.3875(19) . ?
C003 C005 1.3930(17) . ?
C003 C00A 1.3934(18) . ?
C004 H004 0.9300 . ?
C004 C006 1.3800(18) . ?
C005 H005 0.9300 . ?
C005 C00B 1.3795(18) . ?
C006 H006 0.9300 . ?
C006 C007 1.386(2) . ?
C007 C009 1.384(2) . ?
C007 C00E 1.505(2) . ?
C008 H008 0.9300 . ?
C008 C009 1.385(2) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00C 1.375(2) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.374(2) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.382(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9600 . ?
C00E H00F 0.9600 . ?
C00E H00G 0.9600 . ?

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
C002 N001 H001 117.0 . . ?
C003 N001 H001 117.0 . . ?
C003 N001 C002 125.95(10) . . ?
C004 C002 N001 121.69(12) . . ?
C008 C002 N001 120.33(12) . . ?
C008 C002 C004 117.92(12) . . ?
N001 C003 C00A 119.35(12) . . ?
C005 C003 N001 122.17(11) . . ?
C005 C003 C00A 118.44(12) . . ?
C002 C004 H004 119.7 . . ?
C006 C004 C002 120.57(12) . . ?
C006 C004 H004 119.7 . . ?
C003 C005 H005 119.8 . . ?
C00B C005 C003 120.48(12) . . ?
C00B C005 H005 119.8 . . ?
C004 C006 H006 119.1 . . ?
C004 C006 C007 121.89(12) . . ?
C007 C006 H006 119.1 . . ?
C006 C007 C00E 120.80(14) . . ?
C009 C007 C006 117.16(12) . . ?
C009 C007 C00E 122.04(14) . . ?
C002 C008 H008 119.7 . . ?
C009 C008 C002 120.69(12) . . ?
C009 C008 H008 119.7 . . ?
C007 C009 C008 121.75(12) . . ?
C007 C009 H009 119.1 . . ?
C008 C009 H009 119.1 . . ?
C003 C00A H00A 119.8 . . ?
C00C C00A C003 120.30(14) . . ?
C00C C00A H00A 119.8 . . ?
C005 C00B H00B 119.6 . . ?
C00D C00B C005 120.72(14) . . ?
C00D C00B H00B 119.6 . . ?
C00A C00C H00C 119.5 . . ?
C00A C00C C00D 120.92(14) . . ?
C00D C00C H00C 119.5 . . ?
C00B C00D C00C 119.12(14) . . ?
C00B C00D H00D 120.4 . . ?
C00C C00D H00D 120.4 . . ?
C007 C00E H00E 109.5 . . ?
C007 C00E H00F 109.5 . . ?
C007 C00E H00G 109.5 . . ?
H00E C00E H00F 109.5 . . ?
H00E C00E H00G 109.5 . . ?
H00F C00E H00G 109.5 . . ?

_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.642
