# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20190709diamide5_rt
_database_code_depnum_ccdc_archive 'CCDC 2110544'
loop_
_audit_author_name
_audit_author_address
'Tomoyuki Akutagawa'
;Tohoku University
Japan
;
_audit_update_record             
;
2021-09-18 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H28 N2 O2'
_chemical_formula_moiety         'C18 H28 N2 O2'
_chemical_formula_weight         304.43
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.0874(6)
_cell_length_b                   5.1180(6)
_cell_length_c                   16.8328(18)
_cell_angle_alpha                90.632(6)
_cell_angle_beta                 97.129(7)
_cell_angle_gamma                93.262(7)
_cell_volume                     434.12(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      5.30
_cell_measurement_theta_max      68.11
_cell_measurement_temperature    250
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             166.00
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.942

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      250
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            5123
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_theta_max         68.190
_diffrn_reflns_theta_min         5.298
_diffrn_reflns_theta_full        68.190
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1549
_reflns_number_gt                1430
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1340
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1549
_refine_ls_number_parameters     104
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0880P)²+0.0516P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.32
_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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09829(16) 0.35176(18) 0.84550(5) 0.0475(3) Uani 1 1 d . . .
N1 N 0.5234(2) 0.4537(2) 0.82983(6) 0.0416(3) Uani 1 1 d . . .
C1 C 0.2621(2) -0.0531(2) 0.95185(7) 0.0381(3) Uani 1 1 d . . .
H1 H 0.1000 -0.0892 0.9193 0.046 Uiso 1 1 calc R . .
C2 C 0.4280(2) 0.1585(2) 0.93496(7) 0.0347(3) Uani 1 1 d . . .
C3 C 0.6668(2) 0.2108(2) 0.98397(7) 0.0386(3) Uani 1 1 d . . .
H3 H 0.7802 0.3542 0.9733 0.046 Uiso 1 1 calc R . .
C4 C 0.3365(2) 0.3288(2) 0.86628(7) 0.0367(3) Uani 1 1 d . . .
C5 C 0.4549(3) 0.6310(3) 0.76429(7) 0.0433(4) Uani 1 1 d . . .
H5A H 0.3376 0.7606 0.7812 0.052 Uiso 1 1 calc R . .
H5B H 0.3588 0.5315 0.7185 0.052 Uiso 1 1 calc R . .
C6 C 0.6994(3) 0.7695(3) 0.73915(8) 0.0456(4) Uani 1 1 d . . .
H6A H 0.8215 0.6387 0.7260 0.055 Uiso 1 1 calc R . .
H6B H 0.7889 0.8765 0.7842 0.055 Uiso 1 1 calc R . .
C7 C 0.6394(3) 0.9433(3) 0.66755(8) 0.0477(4) Uani 1 1 d . . .
H7A H 0.5388 0.8390 0.6236 0.057 Uiso 1 1 calc R . .
H7B H 0.5277 1.0819 0.6820 0.057 Uiso 1 1 calc R . .
C8 C 0.8863(3) 1.0669(3) 0.63902(9) 0.0620(4) Uani 1 1 d . . .
H8A H 0.9965 0.9277 0.6242 0.074 Uiso 1 1 calc R . .
H8B H 0.9879 1.1684 0.6834 0.074 Uiso 1 1 calc R . .
C9 C 0.8324(5) 1.2445(4) 0.56833(11) 0.0884(6) Uani 1 1 d . . .
H9A H 0.7201 1.3809 0.5820 0.106 Uiso 1 1 calc R . .
H9B H 0.7435 1.1431 0.5227 0.106 Uiso 1 1 calc R . .
H9C H 0.9988 1.3233 0.5550 0.106 Uiso 1 1 calc R . .
H2 H 0.680(4) 0.409(3) 0.8393(9) 0.057(4) Uiso 1 1 d . . .

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
O1 0.0293(6) 0.0620(6) 0.0511(5) 0.0214(4) 0.0021(4) 0.0056(4)
N1 0.0297(6) 0.0525(7) 0.0438(6) 0.0199(5) 0.0051(4) 0.0074(4)
C1 0.0295(7) 0.0462(7) 0.0377(6) 0.0070(5) 0.0006(5) 0.0010(5)
C2 0.0300(6) 0.0405(6) 0.0346(6) 0.0063(4) 0.0056(5) 0.0065(4)
C3 0.0322(7) 0.0414(6) 0.0419(6) 0.0087(5) 0.0036(5) -0.0008(5)
C4 0.0311(7) 0.0417(6) 0.0377(6) 0.0069(5) 0.0038(5) 0.0050(5)
C5 0.0348(7) 0.0521(7) 0.0432(7) 0.0174(6) 0.0028(5) 0.0053(5)
C6 0.0364(7) 0.0537(8) 0.0461(7) 0.0166(6) 0.0025(5) 0.0014(6)
C7 0.0444(8) 0.0525(8) 0.0465(7) 0.0167(6) 0.0048(6) 0.0042(6)
C8 0.0600(10) 0.0665(9) 0.0601(9) 0.0202(7) 0.0131(7) -0.0080(7)
C9 0.1167(17) 0.0807(12) 0.0708(11) 0.0345(10) 0.0277(11) -0.0086(11)

#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
O1 C4 1.2316(15) . ?
N1 C4 1.3317(16) . ?
N1 C5 1.4573(15) . ?
N1 H2 0.835(18) . ?
C1 C3 1.3803(16) 2_657 ?
C1 C2 1.3885(17) . ?
C1 H1 0.9400 . ?
C2 C3 1.3921(17) . ?
C2 C4 1.4991(15) . ?
C3 C1 1.3803(16) 2_657 ?
C3 H3 0.9400 . ?
C5 C6 1.5052(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.5169(16) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.5081(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.513(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?

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
C4 N1 C5 121.25(10) . . ?
C4 N1 H2 118.8(12) . . ?
C5 N1 H2 119.1(12) . . ?
C3 C1 C2 120.62(11) 2_657 . ?
C3 C1 H1 119.7 2_657 . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 119.11(11) . . ?
C1 C2 C4 118.33(10) . . ?
C3 C2 C4 122.52(11) . . ?
C1 C3 C2 120.28(11) 2_657 . ?
C1 C3 H3 119.9 2_657 . ?
C2 C3 H3 119.9 . . ?
O1 C4 N1 122.14(11) . . ?
O1 C4 C2 120.78(11) . . ?
N1 C4 C2 117.08(10) . . ?
N1 C5 C6 111.14(10) . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 113.06(11) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 112.85(11) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 114.02(15) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C3 C1 C2 C3 -0.41(19) 2_657 . . . ?
C3 C1 C2 C4 -177.87(10) 2_657 . . . ?
C1 C2 C3 C1 0.41(19) . . . 2_657 ?
C4 C2 C3 C1 177.76(10) . . . 2_657 ?
C5 N1 C4 O1 1.67(19) . . . . ?
C5 N1 C4 C2 -177.83(10) . . . . ?
C1 C2 C4 O1 27.81(16) . . . . ?
C3 C2 C4 O1 -149.56(12) . . . . ?
C1 C2 C4 N1 -152.68(12) . . . . ?
C3 C2 C4 N1 29.95(16) . . . . ?
C4 N1 C5 C6 173.88(11) . . . . ?
N1 C5 C6 C7 176.35(10) . . . . ?
C5 C6 C7 C8 -176.00(12) . . . . ?
C6 C7 C8 C9 -179.20(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H2 O1 . . 1_655 2.9802(14) 0.835(18) 2.157(18) 168.4(16) no
