# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20231216-cyadi_autored
_database_code_depnum_ccdc_archive 'CCDC 2348426'
loop_
_audit_author_name
_audit_author_address
'Norihito Fukui'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-04-15 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-12-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H28 N2 O4'
_chemical_formula_sum            'C30 H28 N2 O4'
_chemical_formula_weight         480.54
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   22.6197(11)
_cell_length_b                   5.2092(2)
_cell_length_c                   38.7744(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.172(4)
_cell_angle_gamma                90
_cell_volume                     4567.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.2040
_cell_measurement_theta_min      2.7160
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2032
_exptl_crystal_preparation       evaporate
_exptl_crystal_recrystallization_method toluene
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.1255
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            19984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.181
_diffrn_reflns_theta_min         2.740
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn-N'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   30.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   30.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0309811000
_diffrn_orient_matrix_UB_12      0.0059667000
_diffrn_orient_matrix_UB_13      -0.0031060000
_diffrn_orient_matrix_UB_21      -0.0017202000
_diffrn_orient_matrix_UB_22      -0.1357420000
_diffrn_orient_matrix_UB_23      0.0010015000
_diffrn_orient_matrix_UB_31      -0.0045408000
_diffrn_orient_matrix_UB_32      0.0084081000
_diffrn_orient_matrix_UB_33      0.0180119000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tubee'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3498
_reflns_number_total             6579
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.030
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00P(H00D,H00H), C00T(H00I,H00K), C00U(H00L,H00M), C00V(H00N,
 H00O), C00W(H00P,H00Q), C00X(H00T,H00U), C00Y(H00V,H00W), C00Z(H00X,H00Y),
 C010(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00R(H00R)
;
_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
O001 O 0.50242(9) 0.2762(4) 0.41715(5) 0.0246(5) Uani 1 1 d . . . . .
O002 O 0.66058(9) 0.9900(4) 0.14645(5) 0.0244(5) Uani 1 1 d . . . . .
O003 O 0.40158(9) 0.9837(4) 0.37821(5) 0.0236(5) Uani 1 1 d . . . . .
O004 O 0.76398(9) 0.2920(4) 0.18595(5) 0.0285(5) Uani 1 1 d . . . . .
N005 N 0.72064(10) 0.6400(5) 0.15861(6) 0.0208(5) Uani 1 1 d . . . . .
N006 N 0.44305(10) 0.6281(5) 0.40517(6) 0.0209(5) Uani 1 1 d . . . . .
C007 C 0.56387(12) 0.5039(5) 0.31211(7) 0.0192(6) Uani 1 1 d . . . . .
C008 C 0.53320(12) 0.7308(5) 0.30037(7) 0.0195(6) Uani 1 1 d . . . . .
C009 C 0.48832(12) 0.8394(6) 0.32095(7) 0.0204(6) Uani 1 1 d . . . . .
H009 H 0.467644 0.984471 0.313620 0.024 Uiso 1 1 calc R U . . .
C00A C 0.50684(12) 0.5057(5) 0.36306(7) 0.0205(6) Uani 1 1 d . . . . .
C00B C 0.47650(12) 0.7272(5) 0.35131(7) 0.0190(6) Uani 1 1 d . . . . .
C00C C 0.54804(12) 0.8374(5) 0.26895(7) 0.0202(6) Uani 1 1 d . . . . .
H00C H 0.527591 0.981564 0.261095 0.024 Uiso 1 1 calc R U . . .
C00D C 0.62387(12) 0.5132(5) 0.26091(7) 0.0211(6) Uani 1 1 d . . . . .
C00E C 0.60738(12) 0.8485(6) 0.21657(7) 0.0207(6) Uani 1 1 d . . . . .
H00E H 0.587462 0.992485 0.208204 0.025 Uiso 1 1 calc R U . . .
C00F C 0.54952(12) 0.3935(6) 0.34449(7) 0.0212(6) Uani 1 1 d . . . . .
H00F H 0.569063 0.247857 0.352629 0.025 Uiso 1 1 calc R U . . .
C00G C 0.60838(12) 0.4036(6) 0.29208(7) 0.0218(6) Uani 1 1 d . . . . .
H00G H 0.628532 0.258254 0.299779 0.026 Uiso 1 1 calc R U . . .
C00H C 0.59215(12) 0.7366(5) 0.24897(7) 0.0203(6) Uani 1 1 d . . . . .
C00I C 0.65104(12) 0.7409(5) 0.19854(7) 0.0197(6) Uani 1 1 d . . . . .
C00J C 0.75454(12) 0.6501(6) 0.12714(7) 0.0212(6) Uani 1 1 d . . . . .
H00J H 0.738488 0.792435 0.113323 0.025 Uiso 1 1 calc R U . . .
C00K C 0.72757(13) 0.4604(6) 0.18473(7) 0.0221(6) Uani 1 1 d . . . . .
C00L C 0.68217(12) 0.5237(6) 0.21051(7) 0.0221(6) Uani 1 1 d . . . . .
C00M C 0.48562(12) 0.4451(5) 0.39786(7) 0.0205(6) Uani 1 1 d . . . . .
C00N C 0.78024(13) 0.4391(6) 0.07217(7) 0.0270(7) Uani 1 1 d . . . . .
H00A H 0.776673 0.281930 0.058878 0.032 Uiso 1 1 calc R U . . .
H00B H 0.762361 0.576576 0.058684 0.032 Uiso 1 1 calc R U . . .
C00O C 0.67514(13) 0.8140(6) 0.16494(7) 0.0218(6) Uani 1 1 d . . . . .
C00P C 0.84440(13) 0.4979(6) 0.07849(7) 0.0259(7) Uani 1 1 d . . . . .
H00D H 0.863457 0.525205 0.056612 0.031 Uiso 1 1 calc R U . . .
H00H H 0.863376 0.352744 0.089815 0.031 Uiso 1 1 calc R U . . .
C00Q C 0.43494(13) 0.8047(6) 0.37839(7) 0.0215(6) Uani 1 1 d . . . . .
C00R C 0.67033(13) 0.4100(6) 0.24090(7) 0.0226(6) Uani 1 1 d . . . . .
H00R H 0.691894 0.268237 0.248543 0.027 Uiso 1 1 calc R U . . .
C00S C 0.41129(12) 0.6498(6) 0.43733(7) 0.0208(6) Uani 1 1 d . . . . .
H00S H 0.383307 0.792351 0.434569 0.025 Uiso 1 1 calc R U . . .
C00T C 0.81861(13) 0.7112(6) 0.13466(8) 0.0286(7) Uani 1 1 d . . . . .
H00I H 0.836175 0.576231 0.148718 0.034 Uiso 1 1 calc R U . . .
H00K H 0.821600 0.871039 0.147418 0.034 Uiso 1 1 calc R U . . .
C00U C 0.74721(13) 0.4090(6) 0.10557(7) 0.0261(7) Uani 1 1 d . . . . .
H00L H 0.705591 0.379281 0.100540 0.031 Uiso 1 1 calc R U . . .
H00M H 0.762583 0.262372 0.118290 0.031 Uiso 1 1 calc R U . . .
C00V C 0.45304(13) 0.7184(6) 0.46724(7) 0.0242(7) Uani 1 1 d . . . . .
H00N H 0.482080 0.583104 0.470479 0.029 Uiso 1 1 calc R U . . .
H00O H 0.473878 0.876001 0.462011 0.029 Uiso 1 1 calc R U . . .
C00W C 0.37524(13) 0.4106(6) 0.44484(7) 0.0252(7) Uani 1 1 d . . . . .
H00P H 0.401336 0.263427 0.447015 0.030 Uiso 1 1 calc R U . . .
H00Q H 0.347555 0.378453 0.425898 0.030 Uiso 1 1 calc R U . . .
C00X C 0.38277(13) 0.5147(6) 0.50784(7) 0.0265(7) Uani 1 1 d . . . . .
H00T H 0.409270 0.371970 0.512553 0.032 Uiso 1 1 calc R U . . .
H00U H 0.359845 0.545006 0.528309 0.032 Uiso 1 1 calc R U . . .
C00Y C 0.34162(13) 0.4462(6) 0.47810(7) 0.0269(7) Uani 1 1 d . . . . .
H00V H 0.312520 0.581411 0.474936 0.032 Uiso 1 1 calc R U . . .
H00W H 0.320778 0.288906 0.483437 0.032 Uiso 1 1 calc R U . . .
C00Z C 0.41879(14) 0.7526(6) 0.49985(7) 0.0260(7) Uani 1 1 d . . . . .
H00X H 0.392534 0.898946 0.497313 0.031 Uiso 1 1 calc R U . . .
H00Y H 0.446049 0.787355 0.518920 0.031 Uiso 1 1 calc R U . . .
C010 C 0.85196(14) 0.7351(6) 0.10083(8) 0.0315(8) Uani 1 1 d . . . . .
H01A H 0.837482 0.883849 0.088202 0.038 Uiso 1 1 calc R U . . .
H01B H 0.893675 0.761320 0.105957 0.038 Uiso 1 1 calc R U . . .


_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
O001 C00M 1.211(3) . ?
O002 C00O 1.205(3) . ?
O003 C00Q 1.199(3) . ?
O004 C00K 1.204(3) . ?
N005 C00J 1.455(3) . ?
N005 C00K 1.385(4) . ?
N005 C00O 1.397(4) . ?
N006 C00M 1.388(4) . ?
N006 C00Q 1.396(4) . ?
N006 C00S 1.456(3) . ?
C007 C008 1.440(4) . ?
C007 C00F 1.424(4) . ?
C007 C00G 1.386(4) . ?
C008 C009 1.422(4) . ?
C008 C00C 1.386(4) . ?
C009 H009 0.9300 . ?
C009 C00B 1.346(4) . ?
C00A C00B 1.413(4) . ?
C00A C00F 1.349(4) . ?
C00A C00M 1.476(4) . ?
C00B C00Q 1.480(4) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.380(4) . ?
C00D C00G 1.388(4) . ?
C00D C00H 1.439(4) . ?
C00D C00R 1.424(4) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.433(4) . ?
C00E C00I 1.344(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00I C00L 1.406(4) . ?
C00I C00O 1.473(4) . ?
C00J H00J 0.9800 . ?
C00J C00T 1.507(4) . ?
C00J C00U 1.516(4) . ?
C00K C00L 1.485(4) . ?
C00L C00R 1.351(4) . ?
C00N H00A 0.9700 . ?
C00N H00B 0.9700 . ?
C00N C00P 1.498(4) . ?
C00N C00U 1.517(4) . ?
C00P H00D 0.9700 . ?
C00P H00H 0.9700 . ?
C00P C010 1.516(4) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9800 . ?
C00S C00V 1.523(4) . ?
C00S C00W 1.521(4) . ?
C00T H00I 0.9700 . ?
C00T H00K 0.9700 . ?
C00T C010 1.532(4) . ?
C00U H00L 0.9700 . ?
C00U H00M 0.9700 . ?
C00V H00N 0.9700 . ?
C00V H00O 0.9700 . ?
C00V C00Z 1.507(4) . ?
C00W H00P 0.9700 . ?
C00W H00Q 0.9700 . ?
C00W C00Y 1.522(4) . ?
C00X H00T 0.9700 . ?
C00X H00U 0.9700 . ?
C00X C00Y 1.510(4) . ?
C00X C00Z 1.519(4) . ?
C00Y H00V 0.9700 . ?
C00Y H00W 0.9700 . ?
C00Z H00X 0.9700 . ?
C00Z H00Y 0.9700 . ?
C010 H01A 0.9700 . ?
C010 H01B 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
C00K N005 C00J 125.7(2) . . ?
C00K N005 C00O 112.5(2) . . ?
C00O N005 C00J 121.8(2) . . ?
C00M N006 C00Q 112.4(2) . . ?
C00M N006 C00S 125.8(2) . . ?
C00Q N006 C00S 121.7(2) . . ?
C00F C007 C008 119.5(2) . . ?
C00G C007 C008 118.9(3) . . ?
C00G C007 C00F 121.5(3) . . ?
C009 C008 C007 119.6(3) . . ?
C00C C008 C007 118.9(3) . . ?
C00C C008 C009 121.5(3) . . ?
C008 C009 H009 120.8 . . ?
C00B C009 C008 118.4(3) . . ?
C00B C009 H009 120.8 . . ?
C00B C00A C00M 107.7(2) . . ?
C00F C00A C00B 122.0(3) . . ?
C00F C00A C00M 130.2(3) . . ?
C009 C00B C00A 122.2(3) . . ?
C009 C00B C00Q 130.0(3) . . ?
C00A C00B C00Q 107.8(2) . . ?
C008 C00C H00C 118.9 . . ?
C00H C00C C008 122.1(3) . . ?
C00H C00C H00C 118.9 . . ?
C00G C00D C00H 118.7(3) . . ?
C00G C00D C00R 121.4(3) . . ?
C00R C00D C00H 119.9(3) . . ?
C00H C00E H00E 120.7 . . ?
C00I C00E H00E 120.7 . . ?
C00I C00E C00H 118.6(3) . . ?
C007 C00F H00F 120.9 . . ?
C00A C00F C007 118.3(3) . . ?
C00A C00F H00F 120.9 . . ?
C007 C00G C00D 122.2(3) . . ?
C007 C00G H00G 118.9 . . ?
C00D C00G H00G 118.9 . . ?
C00C C00H C00D 119.3(3) . . ?
C00C C00H C00E 121.8(3) . . ?
C00E C00H C00D 118.9(3) . . ?
C00E C00I C00L 122.1(3) . . ?
C00E C00I C00O 129.9(3) . . ?
C00L C00I C00O 107.9(2) . . ?
N005 C00J H00J 106.9 . . ?
N005 C00J C00T 111.5(2) . . ?
N005 C00J C00U 112.3(2) . . ?
C00T C00J H00J 106.9 . . ?
C00T C00J C00U 112.1(2) . . ?
C00U C00J H00J 106.9 . . ?
O004 C00K N005 126.0(3) . . ?
O004 C00K C00L 128.1(3) . . ?
N005 C00K C00L 105.8(2) . . ?
C00I C00L C00K 107.8(2) . . ?
C00R C00L C00I 122.3(3) . . ?
C00R C00L C00K 130.0(3) . . ?
O001 C00M N006 125.7(3) . . ?
O001 C00M C00A 128.0(3) . . ?
N006 C00M C00A 106.2(2) . . ?
H00A C00N H00B 107.9 . . ?
C00P C00N H00A 109.2 . . ?
C00P C00N H00B 109.2 . . ?
C00P C00N C00U 111.9(2) . . ?
C00U C00N H00A 109.2 . . ?
C00U C00N H00B 109.2 . . ?
O002 C00O N005 125.6(3) . . ?
O002 C00O C00I 128.4(3) . . ?
N005 C00O C00I 106.0(2) . . ?
C00N C00P H00D 109.5 . . ?
C00N C00P H00H 109.5 . . ?
C00N C00P C010 110.9(3) . . ?
H00D C00P H00H 108.0 . . ?
C010 C00P H00D 109.5 . . ?
C010 C00P H00H 109.5 . . ?
O003 C00Q N006 126.1(3) . . ?
O003 C00Q C00B 128.1(3) . . ?
N006 C00Q C00B 105.8(2) . . ?
C00D C00R H00R 120.9 . . ?
C00L C00R C00D 118.1(3) . . ?
C00L C00R H00R 120.9 . . ?
N006 C00S H00S 107.1 . . ?
N006 C00S C00V 111.2(2) . . ?
N006 C00S C00W 112.1(2) . . ?
C00V C00S H00S 107.1 . . ?
C00W C00S H00S 107.1 . . ?
C00W C00S C00V 111.9(2) . . ?
C00J C00T H00I 109.7 . . ?
C00J C00T H00K 109.7 . . ?
C00J C00T C010 109.9(2) . . ?
H00I C00T H00K 108.2 . . ?
C010 C00T H00I 109.7 . . ?
C010 C00T H00K 109.7 . . ?
C00J C00U C00N 109.6(2) . . ?
C00J C00U H00L 109.8 . . ?
C00J C00U H00M 109.8 . . ?
C00N C00U H00L 109.8 . . ?
C00N C00U H00M 109.8 . . ?
H00L C00U H00M 108.2 . . ?
C00S C00V H00N 109.6 . . ?
C00S C00V H00O 109.6 . . ?
H00N C00V H00O 108.1 . . ?
C00Z C00V C00S 110.2(2) . . ?
C00Z C00V H00N 109.6 . . ?
C00Z C00V H00O 109.6 . . ?
C00S C00W H00P 109.7 . . ?
C00S C00W H00Q 109.7 . . ?
C00S C00W C00Y 110.0(2) . . ?
H00P C00W H00Q 108.2 . . ?
C00Y C00W H00P 109.7 . . ?
C00Y C00W H00Q 109.7 . . ?
H00T C00X H00U 108.0 . . ?
C00Y C00X H00T 109.4 . . ?
C00Y C00X H00U 109.4 . . ?
C00Y C00X C00Z 111.2(2) . . ?
C00Z C00X H00T 109.4 . . ?
C00Z C00X H00U 109.4 . . ?
C00W C00Y H00V 109.3 . . ?
C00W C00Y H00W 109.3 . . ?
C00X C00Y C00W 111.4(2) . . ?
C00X C00Y H00V 109.3 . . ?
C00X C00Y H00W 109.3 . . ?
H00V C00Y H00W 108.0 . . ?
C00V C00Z C00X 111.2(2) . . ?
C00V C00Z H00X 109.4 . . ?
C00V C00Z H00Y 109.4 . . ?
C00X C00Z H00X 109.4 . . ?
C00X C00Z H00Y 109.4 . . ?
H00X C00Z H00Y 108.0 . . ?
C00P C010 C00T 111.8(3) . . ?
C00P C010 H01A 109.3 . . ?
C00P C010 H01B 109.3 . . ?
C00T C010 H01A 109.3 . . ?
C00T C010 H01B 109.3 . . ?
H01A C010 H01B 107.9 . . ?

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
O004 C00K C00L C00I 178.0(3) . . . . ?
O004 C00K C00L C00R -0.6(5) . . . . ?
N005 C00J C00T C010 -176.8(2) . . . . ?
N005 C00J C00U C00N 176.3(2) . . . . ?
N005 C00K C00L C00I -0.8(3) . . . . ?
N005 C00K C00L C00R -179.4(3) . . . . ?
N006 C00S C00V C00Z 177.2(2) . . . . ?
N006 C00S C00W C00Y -178.4(2) . . . . ?
C007 C008 C009 C00B 1.0(4) . . . . ?
C007 C008 C00C C00H -1.5(4) . . . . ?
C008 C007 C00F C00A 0.6(4) . . . . ?
C008 C007 C00G C00D -0.8(4) . . . . ?
C008 C009 C00B C00A -0.5(4) . . . . ?
C008 C009 C00B C00Q 176.6(3) . . . . ?
C008 C00C C00H C00D 0.2(4) . . . . ?
C008 C00C C00H C00E -179.8(3) . . . . ?
C009 C008 C00C C00H 178.9(2) . . . . ?
C009 C00B C00Q O003 2.2(5) . . . . ?
C009 C00B C00Q N006 -176.6(3) . . . . ?
C00A C00B C00Q O003 179.6(3) . . . . ?
C00A C00B C00Q N006 0.8(3) . . . . ?
C00B C00A C00F C007 -0.1(4) . . . . ?
C00B C00A C00M O001 -176.8(3) . . . . ?
C00B C00A C00M N006 1.1(3) . . . . ?
C00C C008 C009 C00B -179.5(3) . . . . ?
C00E C00I C00L C00K -178.9(3) . . . . ?
C00E C00I C00L C00R -0.2(4) . . . . ?
C00E C00I C00O O002 0.5(5) . . . . ?
C00E C00I C00O N005 179.0(3) . . . . ?
C00F C007 C008 C009 -1.0(4) . . . . ?
C00F C007 C008 C00C 179.4(3) . . . . ?
C00F C007 C00G C00D -178.3(3) . . . . ?
C00F C00A C00B C009 0.0(4) . . . . ?
C00F C00A C00B C00Q -177.6(3) . . . . ?
C00F C00A C00M O001 -0.7(5) . . . . ?
C00F C00A C00M N006 177.2(3) . . . . ?
C00G C007 C008 C009 -178.6(2) . . . . ?
C00G C007 C008 C00C 1.8(4) . . . . ?
C00G C007 C00F C00A 178.1(3) . . . . ?
C00G C00D C00H C00C 0.9(4) . . . . ?
C00G C00D C00H C00E -179.1(3) . . . . ?
C00G C00D C00R C00L 178.8(3) . . . . ?
C00H C00D C00G C007 -0.6(4) . . . . ?
C00H C00D C00R C00L -1.6(4) . . . . ?
C00H C00E C00I C00L -0.2(4) . . . . ?
C00H C00E C00I C00O 179.6(3) . . . . ?
C00I C00E C00H C00C 179.7(3) . . . . ?
C00I C00E C00H C00D -0.3(4) . . . . ?
C00I C00L C00R C00D 1.1(4) . . . . ?
C00J N005 C00K O004 2.9(5) . . . . ?
C00J N005 C00K C00L -178.2(2) . . . . ?
C00J N005 C00O O002 -2.5(4) . . . . ?
C00J N005 C00O C00I 179.1(2) . . . . ?
C00J C00T C010 C00P -54.6(4) . . . . ?
C00K N005 C00J C00T -66.0(4) . . . . ?
C00K N005 C00J C00U 60.7(4) . . . . ?
C00K N005 C00O O002 179.2(3) . . . . ?
C00K N005 C00O C00I 0.7(3) . . . . ?
C00K C00L C00R C00D 179.5(3) . . . . ?
C00L C00I C00O O002 -179.7(3) . . . . ?
C00L C00I C00O N005 -1.2(3) . . . . ?
C00M N006 C00Q O003 -178.9(3) . . . . ?
C00M N006 C00Q C00B -0.1(3) . . . . ?
C00M N006 C00S C00V 65.3(3) . . . . ?
C00M N006 C00S C00W -60.8(3) . . . . ?
C00M C00A C00B C009 176.5(3) . . . . ?
C00M C00A C00B C00Q -1.2(3) . . . . ?
C00M C00A C00F C007 -175.6(3) . . . . ?
C00N C00P C010 C00T 54.7(4) . . . . ?
C00O N005 C00J C00T 115.9(3) . . . . ?
C00O N005 C00J C00U -117.4(3) . . . . ?
C00O N005 C00K O004 -178.8(3) . . . . ?
C00O N005 C00K C00L 0.0(3) . . . . ?
C00O C00I C00L C00K 1.3(3) . . . . ?
C00O C00I C00L C00R 180.0(3) . . . . ?
C00P C00N C00U C00J 56.7(3) . . . . ?
C00Q N006 C00M O001 177.4(3) . . . . ?
C00Q N006 C00M C00A -0.6(3) . . . . ?
C00Q N006 C00S C00V -111.6(3) . . . . ?
C00Q N006 C00S C00W 122.3(3) . . . . ?
C00R C00D C00G C007 179.0(3) . . . . ?
C00R C00D C00H C00C -178.7(3) . . . . ?
C00R C00D C00H C00E 1.2(4) . . . . ?
C00S N006 C00M O001 0.2(4) . . . . ?
C00S N006 C00M C00A -177.7(2) . . . . ?
C00S N006 C00Q O003 -1.7(4) . . . . ?
C00S N006 C00Q C00B 177.1(2) . . . . ?
C00S C00V C00Z C00X 56.1(3) . . . . ?
C00S C00W C00Y C00X -55.4(3) . . . . ?
C00T C00J C00U C00N -57.3(3) . . . . ?
C00U C00J C00T C010 56.3(3) . . . . ?
C00U C00N C00P C010 -55.9(3) . . . . ?
C00V C00S C00W C00Y 55.9(3) . . . . ?
C00W C00S C00V C00Z -56.6(3) . . . . ?
C00Y C00X C00Z C00V -56.5(3) . . . . ?
C00Z C00X C00Y C00W 56.0(3) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# 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_20230601-fbutyl-pzbi_autored
_database_code_depnum_ccdc_archive 'CCDC 2348428'
loop_
_audit_author_name
_audit_author_address
'Norihito Fukui'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-04-15 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   5.2387(3)
_cell_length_b                   5.8596(4)
_cell_length_c                   21.0219(14)
_cell_angle_alpha                92.930(5)
_cell_angle_beta                 94.979(5)
_cell_angle_gamma                96.674(5)
_cell_volume                     637.289
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O1 O 0.6384(4) 0.7880(3) 0.34340(10)
O2 O -0.1190(4) 0.3272(4) 0.28703(10)
N1 N 0.2654(4) -0.1442(3) 0.48218(9)
N2 N 0.2515(4) 0.5866(4) 0.30198(10)
C1 C 0.3299(4) 0.0448(4) 0.45104(11)
C6 C 0.4296(4) -0.1911(4) 0.53070(11)
C7 C 0.0905(5) 0.3900(5) 0.31467(12)
C2 C 0.1590(4) 0.0993(4) 0.39970(12)
H2 H 0.003790 0.007204 0.387647
C3 C 0.2291(4) 0.2896(4) 0.36887(11)
C4 C 0.4646(4) 0.4328(4) 0.38635(11)
C8 C 0.4767(5) 0.6252(4) 0.34312(12)
C5 C 0.6324(4) 0.3906(4) 0.43500(11)
H5 H 0.784478 0.488400 0.445978
C9 C 0.1857(6) 0.7403(5) 0.25305(14)
H9A H 0.262377 0.895715 0.266694
H9B H -0.000188 0.739813 0.247929
F4 F 0.0424(8) 0.9563(8) 0.1471(2)
C10 C 0.2767(8) 0.6736(7) 0.19020(17)
C11 C 0.2463(12) 0.8530(16) 0.1413(3)
F6 F 0.2790(18) 0.984(3) 0.0414(4)
F5 F 0.4859(15) 0.7111(19) 0.0689(2)
C12 C 0.309(2) 0.793(3) 0.0750(4)
F7 F 0.109(2) 0.682(3) 0.0475(3)
F1 F 0.5018(13) 0.6130(14) 0.1945(3)
F2 F 0.1046(12) 0.4918(9) 0.1650(2)
F3 F 0.4478(12) 1.0323(10) 0.1649(3)
O1 O 0.3616(4) -0.7880(3) 0.65660(10)
O2 O 1.1190(4) -0.3272(4) 0.71297(10)
N1 N 0.7346(4) 0.1442(3) 0.51782(9)
N2 N 0.7485(4) -0.5866(4) 0.69802(10)
C1 C 0.6701(4) -0.0448(4) 0.54896(11)
C6 C 0.5704(4) 0.1911(4) 0.46930(11)
C7 C 0.9095(5) -0.3900(5) 0.68533(12)
C2 C 0.8410(4) -0.0993(4) 0.60030(12)
H2 H 0.996210 -0.007204 0.612353
C3 C 0.7709(4) -0.2896(4) 0.63113(11)
C4 C 0.5354(4) -0.4328(4) 0.61365(11)
C8 C 0.5233(5) -0.6252(4) 0.65688(12)
C5 C 0.3676(4) -0.3906(4) 0.56500(11)
H5 H 0.215522 -0.488400 0.554022
C9 C 0.8143(6) -0.7403(5) 0.74695(14)
H9A H 0.737623 -0.895715 0.733306
H9B H 1.000188 -0.739813 0.752071
F4 F 0.9576(8) -0.9563(8) 0.8529(2)
C10 C 0.7233(8) -0.6736(7) 0.80980(17)
C11 C 0.7537(12) -0.8530(16) 0.8587(3)
F6 F 0.7210(18) -0.984(3) 0.9586(4)
F5 F 0.5141(15) -0.7111(19) 0.9311(2)
C12 C 0.691(2) -0.793(3) 0.9250(4)
F7 F 0.891(2) -0.682(3) 0.9525(3)
F1 F 0.4982(13) -0.6130(14) 0.8055(3)
F2 F 0.8954(12) -0.4918(9) 0.8350(2)
F3 F 0.5522(12) -1.0323(10) 0.8351(3)
F1A F 0.556(2) 0.763(6) 0.2002(9)
F2A F 0.314(7) 0.446(4) 0.1817(8)
F3A F -0.030(2) 0.643(4) 0.1158(5)
O1 O -0.3616(4) -0.2120(3) 0.34340(10)
O2 O -1.1190(4) -0.6728(4) 0.28703(10)
N1 N -0.7346(4) -1.1442(3) 0.48218(9)
N2 N -0.7485(4) -0.4134(4) 0.30198(10)
C1 C -0.6701(4) -0.9552(4) 0.45104(11)
C6 C -0.5704(4) -1.1911(4) 0.53070(11)
C7 C -0.9095(5) -0.6100(5) 0.31467(12)
C2 C -0.8410(4) -0.9007(4) 0.39970(12)
H2 H -0.996210 -0.992796 0.387647
C3 C -0.7709(4) -0.7104(4) 0.36887(11)
C4 C -0.5354(4) -0.5672(4) 0.38635(11)
C8 C -0.5233(5) -0.3748(4) 0.34312(12)
C5 C -0.3676(4) -0.6094(4) 0.43500(11)
H5 H -0.215522 -0.511600 0.445978
C9 C -0.8143(6) -0.2597(5) 0.25305(14)
H9A H -0.737623 -0.104285 0.266694
H9B H -1.000188 -0.260187 0.247929
F4 F -0.9576(8) -0.0437(8) 0.1471(2)
C10 C -0.7233(8) -0.3264(7) 0.19020(17)
C11 C -0.7537(12) -0.1470(16) 0.1413(3)
F6 F -0.7210(18) -0.016(3) 0.0414(4)
F5 F -0.5141(15) -0.2889(19) 0.0689(2)
C12 C -0.691(2) -0.207(3) 0.0750(4)
F7 F -0.891(2) -0.318(3) 0.0475(3)
F1 F -0.4982(13) -0.3870(14) 0.1945(3)
F2 F -0.8954(12) -0.5082(9) 0.1650(2)
F3 F -0.5522(12) 0.0323(10) 0.1649(3)
O1 O -0.6384(4) -1.7880(3) 0.65660(10)
O2 O 0.1190(4) -1.3272(4) 0.71297(10)
N1 N -0.2654(4) -0.8558(3) 0.51782(9)
N2 N -0.2515(4) -1.5866(4) 0.69802(10)
C1 C -0.3299(4) -1.0448(4) 0.54896(11)
C6 C -0.4296(4) -0.8089(4) 0.46930(11)
C7 C -0.0905(5) -1.3900(5) 0.68533(12)
C2 C -0.1590(4) -1.0993(4) 0.60030(12)
H2 H -0.003790 -1.007204 0.612353
C3 C -0.2291(4) -1.2896(4) 0.63113(11)
C4 C -0.4646(4) -1.4328(4) 0.61365(11)
C8 C -0.4767(5) -1.6252(4) 0.65688(12)
C5 C -0.6324(4) -1.3906(4) 0.56500(11)
H5 H -0.784478 -1.488400 0.554022
C9 C -0.1857(6) -1.7403(5) 0.74695(14)
H9A H -0.262377 -1.895715 0.733306
H9B H 0.000188 -1.739813 0.752071
F4 F -0.0424(8) -1.9563(8) 0.8529(2)
C10 C -0.2767(8) -1.6736(7) 0.80980(17)
C11 C -0.2463(12) -1.8530(16) 0.8587(3)
F6 F -0.2790(18) -1.984(3) 0.9586(4)
F5 F -0.4859(15) -1.7111(19) 0.9311(2)
C12 C -0.309(2) -1.793(3) 0.9250(4)
F7 F -0.109(2) -1.682(3) 0.9525(3)
F1 F -0.5018(13) -1.6130(14) 0.8055(3)
F2 F -0.1046(12) -1.4918(9) 0.8350(2)
F3 F -0.4478(12) -2.0323(10) 0.8351(3)

#END
####################################################################### 
# 
# 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_20230927-CyHexPzBI-RT_autored
_database_code_depnum_ccdc_archive 'CCDC 2348427'
loop_
_audit_author_name
_audit_author_address
'Norihito Fukui'
;Nagoya University
Japan
;
_audit_update_record             
;
2024-04-15 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C14 H13 N2 O2'
_chemical_formula_sum            'C14 H13 N2 O2'
_chemical_formula_weight         241.272
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.1483(2)
_cell_length_b                   6.1694(2)
_cell_length_c                   18.5347(6)
_cell_angle_alpha                86.250(3)
_cell_angle_beta                 82.260(3)
_cell_angle_gamma                81.884(3)
_cell_volume                     576.85(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.3380
_cell_measurement_theta_min      2.2220
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             254.169
_exptl_crystal_preparation       'vapor diffusion'
_exptl_crystal_recrystallization_method oDCB/octane
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.043
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.9808
_diffrn_reflns_Laue_measured_fraction_max 0.8451
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5396
_diffrn_reflns_point_group_measured_fraction_full 0.9808
_diffrn_reflns_point_group_measured_fraction_max 0.8451
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.83
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_type            'Rigaku Saturn-N'
_diffrn_measured_fraction_theta_full 0.9808
_diffrn_measured_fraction_theta_max 0.8451
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   10.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   10.00    --  -20.00  45.00  90.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1317292000
_diffrn_orient_matrix_UB_12      0.0244200000
_diffrn_orient_matrix_UB_13      -0.0031233000
_diffrn_orient_matrix_UB_21      -0.0071986000
_diffrn_orient_matrix_UB_22      -0.0035369000
_diffrn_orient_matrix_UB_23      0.0385375000
_diffrn_orient_matrix_UB_31      0.0477585000
_diffrn_orient_matrix_UB_32      -0.1136156000
_diffrn_orient_matrix_UB_33      -0.0000002000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating-anode X-ray tubee'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -7
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                2191
_reflns_number_total             3066
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3461
_refine_diff_density_min         -0.3065
_refine_diff_density_rms         0.0628
_refine_ls_d_res_high            0.6934
_refine_ls_d_res_low             9.1726
_refine_ls_goodness_of_fit_ref   1.0383
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.0383
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1749
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.9002(2) 0.28140(18) 0.75431(6) 0.0442(3) Uani 1.000000 .
O2 O 0.1728(2) 0.7311(2) 0.69030(7) 0.0544(4) Uani 1.000000 .
N1 N 0.7198(2) -0.1455(2) 0.52126(7) 0.0353(3) Uani 1.000000 .
N2 N 0.5254(2) 0.5276(2) 0.73990(7) 0.0361(3) Uani 1.000000 .
C1 C 0.6257(3) 0.0398(2) 0.55602(8) 0.0321(3) Uani 1.000000 .
C6 C 0.5966(3) -0.1859(2) 0.46538(8) 0.0326(3) Uani 1.000000 .
C7 C 0.7182(3) 0.3504(2) 0.72072(8) 0.0332(3) Uani 1.000000 .
C4 C 0.4248(3) 0.4106(2) 0.63272(8) 0.0341(4) Uani 1.000000 .
C2 C 0.7521(3) 0.0872(2) 0.61667(8) 0.0351(4) Uani 1.000000 .
C3 C 0.6472(3) 0.2691(2) 0.65297(8) 0.0326(3) Uani 1.000000 .
C9 C 0.5033(3) 0.6315(2) 0.81010(8) 0.0343(4) Uani 1.000000 .
C5 C 0.3046(3) 0.3781(2) 0.57460(8) 0.0360(4) Uani 1.000000 .
C8 C 0.3496(3) 0.5800(3) 0.68834(8) 0.0380(4) Uani 1.000000 .
C14 C 0.5450(3) 0.8717(3) 0.80119(9) 0.0401(4) Uani 1.000000 .
C10 C 0.2419(3) 0.6024(3) 0.85660(9) 0.0435(4) Uani 1.000000 .
C11 C 0.2302(4) 0.6994(3) 0.93091(9) 0.0510(5) Uani 1.000000 .
C12 C 0.2732(4) 0.9380(3) 0.92337(10) 0.0515(5) Uani 1.000000 .
C13 C 0.5330(3) 0.9645(3) 0.87595(10) 0.0485(4) Uani 1.000000 .
H2 H 0.8995(3) -0.0031(2) 0.63038(8) 0.0421(4) Uiso 1.000000 R
H9 H 0.6446(3) 0.5548(2) 0.83646(8) 0.0411(4) Uiso 1.000000 R
H5 H 0.1633(3) 0.4765(2) 0.56106(8) 0.0432(4) Uiso 1.000000 R
H14a H 0.7157(3) 0.8852(3) 0.77317(9) 0.0481(5) Uiso 1.000000 R
H14b H 0.4091(3) 0.9538(3) 0.77500(9) 0.0481(5) Uiso 1.000000 R
H10a H 0.0963(3) 0.6749(3) 0.83196(9) 0.0522(5) Uiso 1.000000 R
H10b H 0.2241(3) 0.4477(3) 0.86316(9) 0.0522(5) Uiso 1.000000 R
H11a H 0.0591(4) 0.6866(3) 0.95881(9) 0.0612(6) Uiso 1.000000 R
H11b H 0.3648(4) 0.6166(3) 0.95741(9) 0.0612(6) Uiso 1.000000 R
H12a H 0.1282(4) 1.0239(3) 0.90168(10) 0.0619(6) Uiso 1.000000 R
H12b H 0.2759(4) 0.9920(3) 0.97121(10) 0.0619(6) Uiso 1.000000 R
H13a H 0.6786(3) 0.8899(3) 0.90015(10) 0.0582(5) Uiso 1.000000 R
H13b H 0.5533(3) 1.1188(3) 0.86995(10) 0.0582(5) Uiso 1.000000 R


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 C7 1.2070(17) . ?
O2 C8 1.2062(18) . ?
N1 C1 1.3461(18) . ?
N1 C6 1.3388(18) . ?
N2 C7 1.3986(18) . ?
N2 C9 1.4715(17) . ?
N2 C8 1.3954(19) . ?
C1 C6 1.437(2) 2_656 ?
C1 C2 1.438(2) . ?
C6 C5 1.4344(19) 2_656 ?
C7 C3 1.490(2) . ?
C4 C3 1.416(2) . ?
C4 C5 1.352(2) . ?
C4 C8 1.491(2) . ?
C2 C3 1.3543(19) . ?
C2 H2 0.9300 . ?
C9 C14 1.522(2) . ?
C9 C10 1.524(2) . ?
C9 H9 0.9800 . ?
C5 H5 0.9300 . ?
C14 C13 1.524(2) . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
C10 C11 1.528(2) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C11 C12 1.514(3) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C12 C13 1.522(2) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C13 H13a 0.9700 . ?
C13 H13b 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
C6 N1 C1 116.57(13) . . ?
C9 N2 C7 122.22(12) . . ?
C8 N2 C7 112.62(13) . . ?
C8 N2 C9 124.98(12) . . ?
C6 C1 N1 121.75(13) 2_656 . ?
C2 C1 N1 117.97(13) . . ?
C2 C1 C6 120.27(13) . 2_656 ?
C1 C6 N1 121.69(13) 2_656 . ?
C5 C6 N1 118.42(13) 2_656 . ?
C5 C6 C1 119.88(13) 2_656 2_656 ?
N2 C7 O1 125.23(14) . . ?
C3 C7 O1 128.92(14) . . ?
C3 C7 N2 105.85(12) . . ?
C5 C4 C3 122.74(14) . . ?
C8 C4 C3 107.82(13) . . ?
C8 C4 C5 129.34(14) . . ?
C3 C2 C1 117.08(13) . . ?
H2 C2 C1 121.46(8) . . ?
H2 C2 C3 121.46(9) . . ?
C4 C3 C7 107.68(12) . . ?
C2 C3 C7 129.59(13) . . ?
C2 C3 C4 122.57(14) . . ?
C14 C9 N2 112.73(12) . . ?
C10 C9 N2 111.24(12) . . ?
C10 C9 C14 111.33(13) . . ?
H9 C9 N2 107.07(7) . . ?
H9 C9 C14 107.07(8) . . ?
H9 C9 C10 107.07(9) . . ?
C4 C5 C6 117.38(14) . 2_656 ?
H5 C5 C6 121.31(8) . 2_656 ?
H5 C5 C4 121.31(9) . . ?
N2 C8 O2 125.82(15) . . ?
C4 C8 O2 128.34(15) . . ?
C4 C8 N2 105.83(13) . . ?
C13 C14 C9 109.67(13) . . ?
H14a C14 C9 109.74(8) . . ?
H14a C14 C13 109.74(9) . . ?
H14b C14 C9 109.74(8) . . ?
H14b C14 C13 109.74(9) . . ?
H14b C14 H14a 108.2 . . ?
C11 C10 C9 110.35(13) . . ?
H10a C10 C9 109.58(9) . . ?
H10a C10 C11 109.58(9) . . ?
H10b C10 C9 109.58(8) . . ?
H10b C10 C11 109.58(9) . . ?
H10b C10 H10a 108.1 . . ?
C12 C11 C10 111.56(14) . . ?
H11a C11 C10 109.31(9) . . ?
H11a C11 C12 109.31(9) . . ?
H11b C11 C10 109.31(9) . . ?
H11b C11 C12 109.31(9) . . ?
H11b C11 H11a 108.0 . . ?
C13 C12 C11 110.45(14) . . ?
H12a C12 C11 109.56(9) . . ?
H12a C12 C13 109.56(10) . . ?
H12b C12 C11 109.56(9) . . ?
H12b C12 C13 109.56(9) . . ?
H12b C12 H12a 108.1 . . ?
C12 C13 C14 111.80(14) . . ?
H13a C13 C14 109.26(9) . . ?
H13a C13 C12 109.26(10) . . ?
H13b C13 C14 109.26(9) . . ?
H13b C13 C12 109.26(10) . . ?
H13b C13 H13a 107.9 . . ?

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
O1 C7 N2 C9 -8.8(2) . . . . ?
O1 C7 N2 C8 175.90(17) . . . . ?
O1 C7 C3 C4 -177.21(18) . . . . ?
O1 C7 C3 C2 7.2(2) . . . . ?
O2 C8 N2 C7 -176.68(19) . . . . ?
O2 C8 N2 C9 8.2(2) . . . . ?
O2 C8 C4 C3 179.2(2) . . . . ?
O2 C8 C4 C5 -4.6(2) . . . . ?
N1 C1 C6 N1 -0.47(15) . . 2_656 2_656 ?
N1 C1 C6 C5 178.08(16) . . 2_656 . ?
N1 C1 C2 C3 -177.09(16) . . . . ?
N1 C6 C1 N1 0.47(15) . . 2_656 2_656 ?
N1 C6 C1 C2 179.49(16) . . 2_656 2_656 ?
N1 C6 C5 C4 -177.20(16) . . 2_656 2_656 ?
N2 C7 C3 C4 3.54(14) . . . . ?
N2 C7 C3 C2 -172.04(12) . . . . ?
N2 C9 C14 C13 -177.17(13) . . . . ?
N2 C9 C10 C11 176.61(13) . . . . ?
N2 C8 C4 C3 -1.65(14) . . . . ?
N2 C8 C4 C5 174.59(12) . . . . ?
C1 C6 C5 C4 -1.40(16) . 2_656 . . ?
C1 C2 C3 C7 174.29(13) . . . . ?
C1 C2 C3 C4 -0.72(18) . . . . ?
C6 C5 C4 C3 2.75(17) 2_656 . . . ?
C6 C5 C4 C8 -173.00(14) 2_656 . . . ?
C7 C3 C4 C5 -177.70(12) . . . . ?
C7 C3 C4 C8 -1.16(14) . . . . ?
C9 C14 C13 C12 -56.88(15) . . . . ?
C9 C10 C11 C12 55.94(15) . . . . ?
C14 C13 C12 C11 56.40(16) . . . . ?
C10 C11 C12 C13 -55.59(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.750
