# Supplementary Information (SI) for ChemComm.
# 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_MEDMEIMINIUM-OTF-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl04b
_database_code_depnum_ccdc_archive 'CCDC 2370791'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C13 H16 F3 N O3 S'
_chemical_formula_moiety         'C13 H16 F3 N O3 S'
_chemical_formula_weight         323.33
_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                   7.1898(2)
_cell_length_b                   10.2610(3)
_cell_length_c                   10.7376(3)
_cell_angle_alpha                82.873(2)
_cell_angle_beta                 81.112(2)
_cell_angle_gamma                73.186(2)
_cell_volume                     746.55(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2972
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336.00
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.932

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

_diffrn_ambient_temperature      123
_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            ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_limit_h_min       9999
_diffrn_reflns_limit_h_max       -9999
_diffrn_reflns_limit_k_min       9999
_diffrn_reflns_limit_k_max       -9999
_diffrn_reflns_limit_l_min       9999
_diffrn_reflns_limit_l_max       -9999
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             0
_reflns_number_gt                2130
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0580
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1340
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     193
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0929P)²] 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         0.39
_refine_diff_density_min         -0.52
_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)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
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_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
S1 S 0.26379(8) 0.79769(6) 0.80178(5) 0.0295(2) Uani 1 1 d . . . . .
F1 F -0.0915(2) 0.88172(19) 0.73817(16) 0.0617(5) Uani 1 1 d . . . . .
F2 F -0.0388(2) 0.69948(18) 0.86398(19) 0.0645(6) Uani 1 1 d . . . . .
F3 F -0.0783(2) 0.89327(18) 0.93328(16) 0.0603(5) Uani 1 1 d . . . . .
O1 O 0.2775(3) 0.9347(2) 0.7792(2) 0.0625(7) Uani 1 1 d . . . . .
O2 O 0.3167(3) 0.7197(2) 0.69381(15) 0.0443(5) Uani 1 1 d . . . . .
O3 O 0.3358(3) 0.7233(2) 0.91408(16) 0.0477(5) Uani 1 1 d . . . . .
N1 N 0.5730(3) 0.7238(2) 0.20423(18) 0.0299(5) Uani 1 1 d . . . . .
C1 C 0.4945(4) 0.8512(2) 0.3893(2) 0.0331(6) Uani 1 1 d . . . . .
H1A H 0.3744 0.9039 0.3543 0.040 Uiso 1 1 calc R U . . .
H1B H 0.5896 0.9050 0.3750 0.040 Uiso 1 1 calc R U . . .
H1C H 0.4643 0.8296 0.4803 0.040 Uiso 1 1 calc R U . . .
C2 C 0.5800(3) 0.7200(3) 0.3250(2) 0.0289(6) Uani 1 1 d . . . . .
C3 C 0.6677(3) 0.5944(2) 0.3965(2) 0.0277(5) Uani 1 1 d . . . . .
H3 H 0.7069 0.5121 0.3555 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6968(3) 0.5879(3) 0.5176(2) 0.0297(6) Uani 1 1 d . . . . .
H4 H 0.6524 0.6712 0.5571 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7897(3) 0.4660(2) 0.5954(2) 0.0292(6) Uani 1 1 d . . . . .
C6 C 0.7933(4) 0.4794(3) 0.7225(2) 0.0342(6) Uani 1 1 d . . . . .
H6 H 0.7384 0.5664 0.7548 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8750(4) 0.3688(3) 0.8020(2) 0.0383(6) Uani 1 1 d . . . . .
H7 H 0.8744 0.3797 0.8887 0.046 Uiso 1 1 calc R U . . .
C8 C 0.9577(4) 0.2424(3) 0.7566(2) 0.0369(6) Uani 1 1 d . . . . .
H8 H 1.0154 0.1666 0.8117 0.044 Uiso 1 1 calc R U . . .
C9 C 0.9566(3) 0.2259(3) 0.6303(2) 0.0359(6) Uani 1 1 d . . . . .
H9 H 1.0136 0.1386 0.5990 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8724(3) 0.3369(3) 0.5497(2) 0.0323(6) Uani 1 1 d . . . . .
H10 H 0.8708 0.3252 0.4635 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6442(3) 0.6016(3) 0.1329(2) 0.0341(6) Uani 1 1 d . . . . .
H11A H 0.6144 0.5233 0.1857 0.041 Uiso 1 1 calc R U . . .
H11B H 0.7861 0.5825 0.1093 0.041 Uiso 1 1 calc R U . . .
H11C H 0.5794 0.6176 0.0564 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4998(4) 0.8525(3) 0.1267(2) 0.0351(6) Uani 1 1 d . . . . .
H12A H 0.3564 0.8811 0.1405 0.042 Uiso 1 1 calc R U . . .
H12B H 0.5440 0.8385 0.0371 0.042 Uiso 1 1 calc R U . . .
H12C H 0.5506 0.9235 0.1509 0.042 Uiso 1 1 calc R U . . .
C13 C 0.0019(4) 0.8188(3) 0.8362(2) 0.0366(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
S1 O1 1.4262(19) . ?
S1 O3 1.4286(17) . ?
S1 O2 1.4307(17) . ?
S1 C13 1.816(3) . ?
F1 C13 1.333(3) . ?
F2 C13 1.328(3) . ?
F3 C13 1.326(3) . ?
N1 C2 1.301(3) . ?
N1 C11 1.471(3) . ?
N1 C12 1.475(3) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.443(3) . ?
C3 C4 1.339(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.462(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 C10 1.402(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O1 S1 O3 116.02(13) . . ?
O1 S1 O2 115.68(13) . . ?
O3 S1 O2 113.83(12) . . ?
O1 S1 C13 103.30(13) . . ?
O3 S1 C13 102.70(11) . . ?
O2 S1 C13 102.63(11) . . ?
C2 N1 C11 123.0(2) . . ?
C2 N1 C12 122.4(2) . . ?
C11 N1 C12 114.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.2(2) . . ?
N1 C2 C1 118.4(2) . . ?
C3 C2 C1 120.4(2) . . ?
C4 C3 C2 123.4(2) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C5 126.9(2) . . ?
C3 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C6 C5 C10 118.5(2) . . ?
C6 C5 C4 117.8(2) . . ?
C10 C5 C4 123.7(2) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3 C13 F2 107.2(2) . . ?
F3 C13 F1 106.5(2) . . ?
F2 C13 F1 107.2(2) . . ?
F3 C13 S1 112.27(18) . . ?
F2 C13 S1 111.73(18) . . ?
F1 C13 S1 111.61(17) . . ?

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
C11 N1 C2 C3 2.9(3) . . . . ?
C12 N1 C2 C3 -174.58(19) . . . . ?
C11 N1 C2 C1 -177.43(19) . . . . ?
C12 N1 C2 C1 5.1(3) . . . . ?
N1 C2 C3 C4 172.8(2) . . . . ?
C1 C2 C3 C4 -6.9(3) . . . . ?
C2 C3 C4 C5 -178.0(2) . . . . ?
C3 C4 C5 C6 -175.5(2) . . . . ?
C3 C4 C5 C10 3.5(4) . . . . ?
C10 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C6 C5 C10 C9 -0.4(3) . . . . ?
C4 C5 C10 C9 -179.5(2) . . . . ?
O1 S1 C13 F3 -57.6(2) . . . . ?
O3 S1 C13 F3 63.4(2) . . . . ?
O2 S1 C13 F3 -178.23(17) . . . . ?
O1 S1 C13 F2 -178.04(18) . . . . ?
O3 S1 C13 F2 -57.0(2) . . . . ?
O2 S1 C13 F2 61.3(2) . . . . ?
O1 S1 C13 F1 61.9(2) . . . . ?
O3 S1 C13 F1 -177.04(18) . . . . ?
O2 S1 C13 F1 -58.7(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_3-Me-PYRROIMINIUM-BF4-3
_audit_block_doi                 10.5517/ccdc.csd.cc2kl08g
_database_code_depnum_ccdc_archive 'CCDC 2370795'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H20 B F4 N'
_chemical_formula_moiety         'C15 H20 B F4 N'
_chemical_formula_weight         301.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.0997(3)
_cell_length_b                   8.3125(2)
_cell_length_c                   17.8495(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.1210(19)
_cell_angle_gamma                90.0000
_cell_volume                     1489.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4242
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.423
_exptl_absorpt_correction_T_max  0.787

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

_diffrn_ambient_temperature      123
_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            8923
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         4.403
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.896
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2438
_reflns_number_gt                1636
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0969
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2424
_refine_ls_wR_factor_gt          0.2185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2438
_refine_ls_number_parameters     192
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1419P)²] 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          0.002
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.39
_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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.09290(19) 0.2202(3) 0.17011(13) 0.0694(8) Uani 1 1 d . . . . .
F2 F 0.29571(18) 0.1873(2) 0.23455(12) 0.0594(7) Uani 1 1 d . . . . .
F3 F 0.1574(2) -0.0245(3) 0.20725(17) 0.0922(10) Uani 1 1 d . . . . .
F4 F 0.2584(3) 0.0948(5) 0.11748(16) 0.1220(13) Uani 1 1 d . . . . .
N1 N 0.2926(2) 0.5088(3) 0.31053(16) 0.0376(7) Uani 1 1 d . . . . .
C1 C 0.1643(3) 0.3932(4) 0.4029(2) 0.0491(9) Uani 1 1 d . . . . .
H1A H 0.0975 0.4738 0.3849 0.059 Uiso 1 1 calc R U . . .
H1B H 0.1760 0.3933 0.4581 0.059 Uiso 1 1 calc R U . . .
H1C H 0.1343 0.2866 0.3847 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2936(3) 0.4325(3) 0.37375(19) 0.0353(8) Uani 1 1 d . . . . .
C3 C 0.4195(3) 0.3832(3) 0.41428(19) 0.0381(8) Uani 1 1 d . . . . .
H3 H 0.4994 0.4191 0.3961 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4292(3) 0.2911(4) 0.47511(19) 0.0409(8) Uani 1 1 d . . . . .
H4 H 0.3481 0.2620 0.4941 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5520(3) 0.2293(4) 0.51619(19) 0.0387(8) Uani 1 1 d . . . . .
C6 C 0.6777(3) 0.2610(4) 0.49265(18) 0.0408(8) Uani 1 1 d . . . . .
H6 H 0.6837 0.3264 0.4495 0.049 Uiso 1 1 calc R U . . .
C7 C 0.7931(3) 0.1992(4) 0.5308(2) 0.0425(8) Uani 1 1 d . . . . .
C8 C 0.7820(3) 0.1055(4) 0.5953(2) 0.0452(9) Uani 1 1 d . . . . .
H8 H 0.8600 0.0636 0.6228 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6589(3) 0.0733(4) 0.6191(2) 0.0470(9) Uani 1 1 d . . . . .
H9 H 0.6527 0.0094 0.6628 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5449(3) 0.1343(4) 0.5793(2) 0.0438(9) Uani 1 1 d . . . . .
H10 H 0.4605 0.1107 0.5955 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9267(3) 0.2326(5) 0.5034(2) 0.0527(9) Uani 1 1 d . . . . .
H11A H 0.9930 0.2510 0.5468 0.063 Uiso 1 1 calc R U . . .
H11B H 0.9202 0.3284 0.4713 0.063 Uiso 1 1 calc R U . . .
H11C H 0.9535 0.1402 0.4745 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1697(3) 0.5563(4) 0.2612(2) 0.0434(9) Uani 1 1 d . . . . .
H12A H 0.1267 0.6509 0.2821 0.052 Uiso 1 1 calc R U . . .
H12B H 0.1050 0.4666 0.2556 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2200(3) 0.5966(4) 0.1864(2) 0.0462(9) Uani 1 1 d . . . . .
H13A H 0.1632 0.6793 0.1590 0.055 Uiso 1 1 calc R U . . .
H13B H 0.2219 0.4997 0.1543 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3601(3) 0.6606(4) 0.2085(2) 0.0455(9) Uani 1 1 d . . . . .
H14A H 0.4152 0.6523 0.1660 0.055 Uiso 1 1 calc R U . . .
H14B H 0.3578 0.7742 0.2250 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4130(3) 0.5521(4) 0.27308(19) 0.0398(8) Uani 1 1 d . . . . .
H15A H 0.4552 0.4548 0.2542 0.048 Uiso 1 1 calc R U . . .
H15B H 0.4791 0.6094 0.3084 0.048 Uiso 1 1 calc R U . . .
B1 B 0.2023(4) 0.1222(5) 0.1805(2) 0.0459(10) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.369(4) . ?
F2 B1 1.386(4) . ?
F3 B1 1.402(5) . ?
F4 B1 1.331(5) . ?
N1 C2 1.294(4) . ?
N1 C15 1.492(4) . ?
N1 C12 1.496(4) . ?
C1 C2 1.493(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.453(4) . ?
C3 C4 1.324(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.465(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.384(4) . ?
C5 C6 1.404(4) . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(5) . ?
C7 C11 1.509(5) . ?
C8 C9 1.382(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.524(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C2 N1 C15 125.3(3) . . ?
C2 N1 C12 124.9(2) . . ?
C15 N1 C12 109.7(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.9(3) . . ?
N1 C2 C1 119.0(3) . . ?
C3 C2 C1 121.1(3) . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 C5 126.7(3) . . ?
C3 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C10 C5 C6 118.5(3) . . ?
C10 C5 C4 119.5(3) . . ?
C6 C5 C4 121.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 118.2(3) . . ?
C6 C7 C11 120.5(3) . . ?
C8 C7 C11 121.3(3) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 104.0(2) . . ?
N1 C12 H12A 111.0 . . ?
C13 C12 H12A 111.0 . . ?
N1 C12 H12B 111.0 . . ?
C13 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C12 C13 C14 103.7(3) . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
C14 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C15 C14 C13 103.4(3) . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14B 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
N1 C15 C14 104.2(2) . . ?
N1 C15 H15A 110.9 . . ?
C14 C15 H15A 110.9 . . ?
N1 C15 H15B 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
F4 B1 F1 113.4(3) . . ?
F4 B1 F2 109.6(3) . . ?
F1 B1 F2 109.9(3) . . ?
F4 B1 F3 108.7(3) . . ?
F1 B1 F3 106.2(3) . . ?
F2 B1 F3 108.8(3) . . ?

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
C15 N1 C2 C3 0.5(4) . . . . ?
C12 N1 C2 C3 175.8(3) . . . . ?
C15 N1 C2 C1 -178.0(3) . . . . ?
C12 N1 C2 C1 -2.7(4) . . . . ?
N1 C2 C3 C4 -172.9(3) . . . . ?
C1 C2 C3 C4 5.5(5) . . . . ?
C2 C3 C4 C5 176.3(3) . . . . ?
C3 C4 C5 C10 179.8(3) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C10 C5 C6 C7 0.2(5) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C5 C6 C7 C11 178.9(3) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C11 C7 C8 C9 -178.9(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C9 C10 C5 -0.8(5) . . . . ?
C6 C5 C10 C9 0.8(5) . . . . ?
C4 C5 C10 C9 179.6(3) . . . . ?
C2 N1 C12 C13 -164.3(3) . . . . ?
C15 N1 C12 C13 11.6(3) . . . . ?
N1 C12 C13 C14 -31.1(3) . . . . ?
C12 C13 C14 C15 39.2(3) . . . . ?
C2 N1 C15 C14 -171.5(3) . . . . ?
C12 N1 C15 C14 12.5(3) . . . . ?
C13 C14 C15 N1 -31.6(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_PYRROIMINIUM-BF4-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl05c
_database_code_depnum_ccdc_archive 'CCDC 2370792'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H18 B F4 N'
_chemical_formula_moiety         'C14 H18 B F4 N'
_chemical_formula_weight         287.11
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.57365(16)
_cell_length_b                   16.3060(3)
_cell_length_c                   9.96321(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.6392(10)
_cell_angle_gamma                90.0000
_cell_volume                     1392.79(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11942
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      68.26
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600.00
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_T_max  0.923

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

_diffrn_ambient_temperature      123
_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            22881
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         5.203
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2500
_reflns_number_gt                1772
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0769
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1223
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2500
_refine_ls_number_parameters     183
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0345P)²+1.8563P] 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         0.33
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(4)

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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.8107(2) 0.77289(10) 0.60887(17) 0.0502(5) Uani 1 1 d . . . . .
F2 F 0.9562(2) 0.88897(11) 0.60059(17) 0.0576(6) Uani 1 1 d . . . . .
F3 F 0.7287(3) 0.88854(14) 0.7083(3) 0.0971(10) Uani 1 1 d . . . . .
F4 F 0.9333(3) 0.82017(15) 0.7928(2) 0.0931(9) Uani 1 1 d . . . . .
N1 N 0.5205(3) 0.69201(13) 0.7018(2) 0.0303(5) Uani 1 1 d . . . . .
C1 C 0.6813(4) 0.59387(18) 0.8183(3) 0.0402(7) Uani 1 1 d . . . . .
H1A H 0.7254 0.5395 0.8004 0.048 Uiso 1 1 calc R U . . .
H1B H 0.6027 0.5895 0.8885 0.048 Uiso 1 1 calc R U . . .
H1C H 0.7646 0.6310 0.8481 0.048 Uiso 1 1 calc R U . . .
C2 C 0.6073(3) 0.62675(16) 0.6930(2) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.6324(3) 0.58904(16) 0.5633(3) 0.0318(6) Uani 1 1 d . . . . .
H3 H 0.5798 0.6113 0.4872 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7268(3) 0.52408(16) 0.5455(3) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.7745 0.5016 0.6238 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7632(3) 0.48460(15) 0.4182(3) 0.0314(6) Uani 1 1 d . . . . .
C6 C 0.6961(3) 0.50821(16) 0.2951(3) 0.0329(6) Uani 1 1 d . . . . .
H6 H 0.6215 0.5513 0.2924 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7380(4) 0.46907(17) 0.1775(3) 0.0388(7) Uani 1 1 d . . . . .
H7 H 0.6918 0.4852 0.0945 0.047 Uiso 1 1 calc R U . . .
C8 C 0.8474(4) 0.40635(18) 0.1807(3) 0.0423(7) Uani 1 1 d . . . . .
H8 H 0.8763 0.3800 0.0997 0.051 Uiso 1 1 calc R U . . .
C9 C 0.9146(3) 0.38199(17) 0.3011(3) 0.0411(7) Uani 1 1 d . . . . .
H9 H 0.9889 0.3388 0.3028 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8729(3) 0.42098(17) 0.4195(3) 0.0364(7) Uani 1 1 d . . . . .
H10 H 0.9194 0.4043 0.5021 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4914(3) 0.73645(17) 0.8287(3) 0.0372(7) Uani 1 1 d . . . . .
H11A H 0.5853 0.7672 0.8581 0.045 Uiso 1 1 calc R U . . .
H11B H 0.4614 0.6979 0.9008 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3590(4) 0.79424(19) 0.7950(3) 0.0427(7) Uani 1 1 d . . . . .
H12A H 0.3665 0.8450 0.8492 0.051 Uiso 1 1 calc R U . . .
H12B H 0.2569 0.7679 0.8116 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3784(4) 0.81284(19) 0.6473(3) 0.0453(8) Uani 1 1 d . . . . .
H13A H 0.4514 0.8591 0.6345 0.054 Uiso 1 1 calc R U . . .
H13B H 0.2768 0.8270 0.6050 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4438(3) 0.73414(16) 0.5871(3) 0.0337(6) Uani 1 1 d . . . . .
H14A H 0.3593 0.6999 0.5484 0.040 Uiso 1 1 calc R U . . .
H14B H 0.5201 0.7466 0.5161 0.040 Uiso 1 1 calc R U . . .
B1 B 0.8571(4) 0.8425(2) 0.6782(3) 0.0363(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.386(4) . ?
F2 B1 1.381(3) . ?
F3 B1 1.368(4) . ?
F4 B1 1.359(4) . ?
N1 C2 1.302(3) . ?
N1 C14 1.481(3) . ?
N1 C11 1.481(3) . ?
C1 C2 1.494(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.449(4) . ?
C3 C4 1.346(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.459(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.400(4) . ?
C5 C6 1.403(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.510(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C2 N1 C14 125.2(2) . . ?
C2 N1 C11 124.0(2) . . ?
C14 N1 C11 110.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.9(2) . . ?
N1 C2 C1 118.3(2) . . ?
C3 C2 C1 121.8(2) . . ?
C4 C3 C2 123.2(3) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 126.6(3) . . ?
C3 C4 H4 116.7 . . ?
C5 C4 H4 116.7 . . ?
C10 C5 C6 118.7(2) . . ?
C10 C5 C4 118.0(2) . . ?
C6 C5 C4 123.3(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
N1 C11 C12 104.4(2) . . ?
N1 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C11 C12 C13 104.5(2) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 105.0(2) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C14 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
N1 C14 C13 104.4(2) . . ?
N1 C14 H14A 110.9 . . ?
C13 C14 H14A 110.9 . . ?
N1 C14 H14B 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
F4 B1 F3 110.1(3) . . ?
F4 B1 F2 109.0(3) . . ?
F3 B1 F2 108.9(3) . . ?
F4 B1 F1 109.4(3) . . ?
F3 B1 F1 109.3(3) . . ?
F2 B1 F1 110.2(2) . . ?

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
C14 N1 C2 C3 -1.1(4) . . . . ?
C11 N1 C2 C3 -178.1(2) . . . . ?
C14 N1 C2 C1 177.5(2) . . . . ?
C11 N1 C2 C1 0.5(4) . . . . ?
N1 C2 C3 C4 176.6(2) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C3 C4 C5 C10 175.7(3) . . . . ?
C3 C4 C5 C6 -3.1(4) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
C4 C5 C10 C9 -178.8(3) . . . . ?
C2 N1 C11 C12 -167.7(2) . . . . ?
C14 N1 C11 C12 14.9(3) . . . . ?
N1 C11 C12 C13 -29.5(3) . . . . ?
C11 C12 C13 C14 33.4(3) . . . . ?
C2 N1 C14 C13 -171.7(2) . . . . ?
C11 N1 C14 C13 5.6(3) . . . . ?
C12 C13 C14 N1 -24.0(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_4-F-PYRROIMINIUM-BF4-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl06d
_database_code_depnum_ccdc_archive 'CCDC 2370793'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H17 B F5 N'
_chemical_formula_moiety         'C14 H17 B F5 N'
_chemical_formula_weight         305.10
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.51495(19)
_cell_length_b                   16.4158(4)
_cell_length_c                   10.0399(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.7420(15)
_cell_angle_gamma                90.0000
_cell_volume                     1403.26(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5950
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      68.15
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    1.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.893

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

_diffrn_ambient_temperature      123
_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            15309
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_theta_max         68.195
_diffrn_reflns_theta_min         5.164
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2566
_reflns_number_gt                2016
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0642
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0924
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     191
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0374P)²+0.8090P] 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         0.23
_refine_diff_density_min         -0.27
_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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.91488(16) 0.38069(8) 0.07907(12) 0.0400(4) Uani 1 1 d . . . . .
F2 F 0.82007(14) 0.76792(7) 0.62619(11) 0.0315(3) Uani 1 1 d . . . . .
F3 F 0.93726(16) 0.89224(7) 0.60725(11) 0.0379(3) Uani 1 1 d . . . . .
F4 F 0.72319(17) 0.87728(9) 0.73569(16) 0.0544(4) Uani 1 1 d . . . . .
F5 F 0.95535(18) 0.82232(9) 0.80001(13) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.51528(18) 0.68758(9) 0.71291(14) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.6741(3) 0.58793(13) 0.82647(19) 0.0278(5) Uani 1 1 d . . . . .
H1A H 0.5919 0.5788 0.8922 0.033 Uiso 1 1 calc R U . . .
H1B H 0.7521 0.6260 0.8629 0.033 Uiso 1 1 calc R U . . .
H1C H 0.7251 0.5360 0.8057 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6024(2) 0.62291(11) 0.70222(18) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.6313(2) 0.58836(11) 0.57182(18) 0.0211(4) Uani 1 1 d . . . . .
H3 H 0.5827 0.6129 0.4961 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7238(2) 0.52321(11) 0.55365(18) 0.0207(4) Uani 1 1 d . . . . .
H4 H 0.7668 0.4987 0.6317 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7656(2) 0.48584(11) 0.42695(18) 0.0193(4) Uani 1 1 d . . . . .
C6 C 0.7036(2) 0.51162(11) 0.30317(18) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.6271 0.5537 0.3000 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7534(2) 0.47602(12) 0.18620(19) 0.0259(5) Uani 1 1 d . . . . .
H7 H 0.7125 0.4934 0.1024 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8642(3) 0.41462(12) 0.1942(2) 0.0275(5) Uani 1 1 d . . . . .
C9 C 0.9260(2) 0.38621(12) 0.3128(2) 0.0262(5) Uani 1 1 d . . . . .
H9 H 1.0008 0.3433 0.3149 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8749(2) 0.42261(11) 0.4290(2) 0.0232(4) Uani 1 1 d . . . . .
H10 H 0.9154 0.4040 0.5122 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4820(3) 0.72908(12) 0.84051(19) 0.0258(5) Uani 1 1 d . . . . .
H11A H 0.5744 0.7605 0.8721 0.031 Uiso 1 1 calc R U . . .
H11B H 0.4528 0.6892 0.9099 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3459(3) 0.78503(13) 0.8073(2) 0.0297(5) Uani 1 1 d . . . . .
H12A H 0.2444 0.7567 0.8189 0.036 Uiso 1 1 calc R U . . .
H12B H 0.3481 0.8341 0.8647 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3700(3) 0.80755(13) 0.6629(2) 0.0298(5) Uani 1 1 d . . . . .
H13A H 0.4422 0.8546 0.6557 0.036 Uiso 1 1 calc R U . . .
H13B H 0.2687 0.8217 0.6193 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4409(2) 0.73224(11) 0.59935(18) 0.0220(4) Uani 1 1 d . . . . .
H14A H 0.3585 0.6986 0.5556 0.026 Uiso 1 1 calc R U . . .
H14B H 0.5200 0.7475 0.5324 0.026 Uiso 1 1 calc R U . . .
B1 B 0.8585(3) 0.84003(14) 0.6923(2) 0.0246(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 C8 1.358(2) . ?
F2 B1 1.394(2) . ?
F3 B1 1.389(3) . ?
F4 B1 1.380(3) . ?
F5 B1 1.382(3) . ?
N1 C2 1.301(2) . ?
N1 C11 1.482(2) . ?
N1 C14 1.490(2) . ?
C1 C2 1.496(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.451(3) . ?
C3 C4 1.342(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.460(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.394(3) . ?
C5 C6 1.409(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C2 N1 C11 124.22(16) . . ?
C2 N1 C14 125.17(15) . . ?
C11 N1 C14 110.57(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.80(17) . . ?
N1 C2 C1 118.12(17) . . ?
C3 C2 C1 122.04(17) . . ?
C4 C3 C2 122.73(18) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 127.10(18) . . ?
C3 C4 H4 116.5 . . ?
C5 C4 H4 116.5 . . ?
C10 C5 C6 118.62(17) . . ?
C10 C5 C4 118.04(17) . . ?
C6 C5 C4 123.32(17) . . ?
C7 C6 C5 120.41(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 118.40(18) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
F1 C8 C9 118.35(19) . . ?
F1 C8 C7 118.29(18) . . ?
C9 C8 C7 123.37(18) . . ?
C8 C9 C10 117.47(18) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C9 C10 C5 121.71(18) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
N1 C11 C12 104.07(15) . . ?
N1 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
C13 C12 C11 104.26(16) . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C12 C13 C14 105.26(16) . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
N1 C14 C13 104.24(15) . . ?
N1 C14 H14A 110.9 . . ?
C13 C14 H14A 110.9 . . ?
N1 C14 H14B 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
F4 B1 F5 109.77(18) . . ?
F4 B1 F3 109.43(18) . . ?
F5 B1 F3 108.83(18) . . ?
F4 B1 F2 109.56(18) . . ?
F5 B1 F2 109.14(18) . . ?
F3 B1 F2 110.09(16) . . ?

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
C11 N1 C2 C3 -178.21(17) . . . . ?
C14 N1 C2 C3 -1.0(3) . . . . ?
C11 N1 C2 C1 0.0(3) . . . . ?
C14 N1 C2 C1 177.23(17) . . . . ?
N1 C2 C3 C4 177.98(18) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -177.28(17) . . . . ?
C3 C4 C5 C10 174.40(18) . . . . ?
C3 C4 C5 C6 -4.2(3) . . . . ?
C10 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 177.08(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 F1 -178.92(17) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
F1 C8 C9 C10 178.85(17) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C9 1.5(3) . . . . ?
C4 C5 C10 C9 -177.21(18) . . . . ?
C2 N1 C11 C12 -165.69(18) . . . . ?
C14 N1 C11 C12 16.7(2) . . . . ?
N1 C11 C12 C13 -31.0(2) . . . . ?
C11 C12 C13 C14 34.2(2) . . . . ?
C2 N1 C14 C13 -173.34(18) . . . . ?
C11 N1 C14 C13 4.2(2) . . . . ?
C12 C13 C14 N1 -23.6(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_4-OMe-PYRROIMINIUM-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0bj
_database_code_depnum_ccdc_archive 'CCDC 2370797'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H20 B F4 N O'
_chemical_formula_moiety         'C15 H20 B F4 N O'
_chemical_formula_weight         317.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.63744(14)
_cell_length_b                   19.6800(4)
_cell_length_c                   10.11448(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.7280(10)
_cell_angle_gamma                90.0000
_cell_volume                     1493.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7354
_cell_measurement_theta_min      4.45
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664.00
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.732

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

_diffrn_ambient_temperature      123
_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            16393
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         4.494
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2723
_reflns_number_gt                2346
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0445
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1012
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2723
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0541P)²+0.4457P] 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         0.28
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0008(2)

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)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.57011(13) 0.85443(5) 0.16949(10) 0.0399(3) Uani 1 1 d . . . . .
F2 F 0.50074(14) 0.76491(5) 0.29190(10) 0.0429(3) Uani 1 1 d . . . . .
F3 F 0.32311(16) 0.85736(5) 0.26330(12) 0.0529(3) Uani 1 1 d . . . . .
F4 F 0.33534(17) 0.78731(6) 0.08701(11) 0.0561(3) Uani 1 1 d . . . . .
O1 O 0.33322(14) 0.56045(5) 0.04923(10) 0.0288(3) Uani 1 1 d . . . . .
N1 N 0.98836(16) 0.36639(6) 0.75844(12) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.66743(19) 0.51645(7) 0.41335(14) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.5813(2) 0.46542(7) 0.32744(14) 0.0253(3) Uani 1 1 d . . . . .
H2 H 0.5996 0.4191 0.3523 0.030 Uiso 1 1 calc R U . . .
C3 C 0.47116(19) 0.48171(7) 0.20811(14) 0.0248(3) Uani 1 1 d . . . . .
H3 H 0.4135 0.4467 0.1516 0.030 Uiso 1 1 calc R U . . .
C4 C 0.44367(19) 0.54999(7) 0.16962(14) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.5247(2) 0.60143(7) 0.25367(14) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.5051 0.6477 0.2287 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6345(2) 0.58431(7) 0.37449(14) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.6886 0.6195 0.4323 0.031 Uiso 1 1 calc R U . . .
C7 C 0.78461(19) 0.50200(8) 0.54062(14) 0.0256(3) Uani 1 1 d . . . . .
H7 H 0.8301 0.5399 0.5944 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8348(2) 0.43993(7) 0.58944(14) 0.0253(3) Uani 1 1 d . . . . .
H8 H 0.7924 0.4015 0.5362 0.030 Uiso 1 1 calc R U . . .
C9 C 0.94921(19) 0.42845(8) 0.71779(14) 0.0250(3) Uani 1 1 d . . . . .
C10 C 1.0226(2) 0.48580(8) 0.80863(14) 0.0306(4) Uani 1 1 d . . . . .
H10A H 0.9827 0.5291 0.7655 0.037 Uiso 1 1 calc R U . . .
H10B H 0.9800 0.4819 0.8939 0.037 Uiso 1 1 calc R U . . .
H10C H 1.1531 0.4839 0.8259 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0997(2) 0.34835(9) 0.89046(14) 0.0310(4) Uani 1 1 d . . . . .
H11A H 1.0526 0.3697 0.9653 0.037 Uiso 1 1 calc R U . . .
H11B H 1.2246 0.3631 0.8950 0.037 Uiso 1 1 calc R U . . .
C12 C 1.0874(2) 0.27127(9) 0.89675(16) 0.0380(4) Uani 1 1 d . . . . .
H12A H 0.9877 0.2572 0.9407 0.046 Uiso 1 1 calc R U . . .
H12B H 1.1996 0.2516 0.9469 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0546(2) 0.24913(9) 0.74954(17) 0.0363(4) Uani 1 1 d . . . . .
H13A H 1.1675 0.2473 0.7150 0.044 Uiso 1 1 calc R U . . .
H13B H 0.9965 0.2040 0.7380 0.044 Uiso 1 1 calc R U . . .
C14 C 0.9323(2) 0.30397(7) 0.67862(15) 0.0277(3) Uani 1 1 d . . . . .
H14A H 0.9483 0.3095 0.5843 0.033 Uiso 1 1 calc R U . . .
H14B H 0.8059 0.2931 0.6792 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3212(2) 0.62846(8) -0.00300(16) 0.0328(4) Uani 1 1 d . . . . .
H15A H 0.2382 0.6294 -0.0894 0.039 Uiso 1 1 calc R U . . .
H15B H 0.2779 0.6588 0.0607 0.039 Uiso 1 1 calc R U . . .
H15C H 0.4391 0.6435 -0.0159 0.039 Uiso 1 1 calc R U . . .
B1 B 0.4322(3) 0.81586(9) 0.20294(17) 0.0285(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.390(2) . ?
F2 B1 1.383(2) . ?
F3 B1 1.387(2) . ?
F4 B1 1.384(2) . ?
O1 C4 1.3618(18) . ?
O1 C15 1.4355(17) . ?
N1 C9 1.3056(19) . ?
N1 C11 1.4865(18) . ?
N1 C14 1.4885(18) . ?
C1 C6 1.402(2) . ?
C1 C2 1.408(2) . ?
C1 C7 1.453(2) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.346(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.441(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.497(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O1 C15 117.18(12) . . ?
C9 N1 C11 124.44(13) . . ?
C9 N1 C14 125.13(12) . . ?
C11 N1 C14 110.42(12) . . ?
C6 C1 C2 117.87(14) . . ?
C6 C1 C7 118.94(13) . . ?
C2 C1 C7 123.17(13) . . ?
C3 C2 C1 120.98(14) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.15(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
O1 C4 C5 124.57(13) . . ?
O1 C4 C3 115.37(12) . . ?
C5 C4 C3 120.05(13) . . ?
C6 C5 C4 119.22(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.70(13) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C1 126.10(13) . . ?
C8 C7 H7 117.0 . . ?
C1 C7 H7 117.0 . . ?
C7 C8 C9 123.79(14) . . ?
C7 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
N1 C9 C8 119.68(13) . . ?
N1 C9 C10 118.33(13) . . ?
C8 C9 C10 121.97(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 104.24(13) . . ?
N1 C11 H11A 110.9 . . ?
C12 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C11 C12 C13 104.12(13) . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 109.0 . . ?
C14 C13 C12 103.47(13) . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
N1 C14 C13 103.94(12) . . ?
N1 C14 H14A 111.0 . . ?
C13 C14 H14A 111.0 . . ?
N1 C14 H14B 111.0 . . ?
C13 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 B1 F4 109.56(13) . . ?
F2 B1 F3 109.04(13) . . ?
F4 B1 F3 109.99(15) . . ?
F2 B1 F1 110.00(14) . . ?
F4 B1 F1 108.98(13) . . ?
F3 B1 F1 109.27(13) . . ?

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
C6 C1 C2 C3 1.2(2) . . . . ?
C7 C1 C2 C3 179.80(13) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C15 O1 C4 C5 9.7(2) . . . . ?
C15 O1 C4 C3 -171.41(12) . . . . ?
C2 C3 C4 O1 179.55(12) . . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
O1 C4 C5 C6 179.81(12) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C7 C1 C6 C5 179.58(13) . . . . ?
C6 C1 C7 C8 -177.23(14) . . . . ?
C2 C1 C7 C8 4.2(2) . . . . ?
C1 C7 C8 C9 -178.87(13) . . . . ?
C11 N1 C9 C8 -177.88(12) . . . . ?
C14 N1 C9 C8 3.7(2) . . . . ?
C11 N1 C9 C10 0.8(2) . . . . ?
C14 N1 C9 C10 -177.55(13) . . . . ?
C7 C8 C9 N1 178.66(13) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C9 N1 C11 C12 173.45(13) . . . . ?
C14 N1 C11 C12 -7.97(15) . . . . ?
N1 C11 C12 C13 27.92(16) . . . . ?
C11 C12 C13 C14 -37.51(17) . . . . ?
C9 N1 C14 C13 163.33(13) . . . . ?
C11 N1 C14 C13 -15.25(15) . . . . ?
C12 C13 C14 N1 32.15(16) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_2-Me-PYRROIMINIUM-BF4-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl07f
_database_code_depnum_ccdc_archive 'CCDC 2370794'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H20 B F4 N'
_chemical_formula_moiety         'C15 H20 B F4 N'
_chemical_formula_weight         301.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5602(3)
_cell_length_b                   15.2074(5)
_cell_length_c                   12.6685(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.164(2)
_cell_angle_gamma                90.0000
_cell_volume                     1450.60(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5031
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      68.06
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.952

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

_diffrn_ambient_temperature      123
_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            16580
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         4.554
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2641
_reflns_number_gt                1678
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0998
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.2621
_refine_ls_wR_factor_gt          0.2250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     192
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1448P)²] 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         0.38
_refine_diff_density_min         -0.34
_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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.5067(3) 0.80299(13) 0.40475(16) 0.0628(7) Uani 1 1 d . . . . .
F2 F 0.5002(3) 0.76393(13) 0.57816(17) 0.0680(7) Uani 1 1 d . . . . .
F3 F 0.3537(3) 0.88416(12) 0.51186(14) 0.0702(8) Uani 1 1 d . . . . .
F4 F 0.2564(3) 0.74799(15) 0.46172(18) 0.0722(7) Uani 1 1 d . . . . .
N1 N 0.3705(3) 0.55176(16) 0.22467(19) 0.0405(7) Uani 1 1 d . . . . .
C1 C 0.3397(5) 0.3964(2) 0.2575(3) 0.0495(9) Uani 1 1 d . . . . .
H1A H 0.3771 0.3589 0.3184 0.059 Uiso 1 1 calc R U . . .
H1B H 0.4231 0.3896 0.2031 0.059 Uiso 1 1 calc R U . . .
H1C H 0.2204 0.3791 0.2281 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3374(4) 0.4906(2) 0.2924(2) 0.0401(8) Uani 1 1 d . . . . .
C3 C 0.2949(4) 0.5153(2) 0.3960(3) 0.0459(8) Uani 1 1 d . . . . .
H3 H 0.2926 0.5762 0.4125 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2585(4) 0.4586(2) 0.4705(3) 0.0475(9) Uani 1 1 d . . . . .
H4 H 0.2629 0.3980 0.4527 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2119(4) 0.4799(2) 0.5781(3) 0.0436(8) Uani 1 1 d . . . . .
C6 C 0.1529(4) 0.4129(2) 0.6444(2) 0.0409(8) Uani 1 1 d . . . . .
C7 C 0.1111(4) 0.4354(2) 0.7458(2) 0.0452(8) Uani 1 1 d . . . . .
H7 H 0.0733 0.3906 0.7909 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1230(4) 0.5208(2) 0.7826(3) 0.0477(9) Uani 1 1 d . . . . .
H8 H 0.0923 0.5345 0.8518 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1807(5) 0.5868(2) 0.7170(3) 0.0494(9) Uani 1 1 d . . . . .
H9 H 0.1903 0.6457 0.7417 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2238(4) 0.5662(2) 0.6160(3) 0.0478(9) Uani 1 1 d . . . . .
H10 H 0.2621 0.6116 0.5717 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1313(4) 0.3193(2) 0.6081(3) 0.0507(9) Uani 1 1 d . . . . .
H11A H 0.0434 0.3165 0.5464 0.061 Uiso 1 1 calc R U . . .
H11B H 0.0909 0.2834 0.6655 0.061 Uiso 1 1 calc R U . . .
H11C H 0.2455 0.2969 0.5886 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4091(5) 0.5358(2) 0.1123(2) 0.0471(9) Uani 1 1 d . . . . .
H12A H 0.3203 0.4955 0.0762 0.057 Uiso 1 1 calc R U . . .
H12B H 0.5290 0.5103 0.1093 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3978(5) 0.6256(2) 0.0628(3) 0.0500(9) Uani 1 1 d . . . . .
H13A H 0.2742 0.6396 0.0355 0.060 Uiso 1 1 calc R U . . .
H13B H 0.4751 0.6298 0.0040 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4615(5) 0.6868(2) 0.1529(3) 0.0530(9) Uani 1 1 d . . . . .
H14A H 0.4186 0.7476 0.1389 0.064 Uiso 1 1 calc R U . . .
H14B H 0.5928 0.6874 0.1642 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3797(4) 0.64715(19) 0.2483(2) 0.0449(8) Uani 1 1 d . . . . .
H15A H 0.4554 0.6587 0.3147 0.054 Uiso 1 1 calc R U . . .
H15B H 0.2598 0.6716 0.2549 0.054 Uiso 1 1 calc R U . . .
B1 B 0.4027(6) 0.8002(2) 0.4907(3) 0.0456(9) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.400(4) . ?
F2 B1 1.388(4) . ?
F3 B1 1.363(4) . ?
F4 B1 1.384(5) . ?
N1 C2 1.305(4) . ?
N1 C15 1.482(4) . ?
N1 C12 1.498(4) . ?
C1 C2 1.499(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.430(4) . ?
C3 C4 1.325(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.474(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.398(4) . ?
C5 C6 1.418(4) . ?
C6 C7 1.392(4) . ?
C6 C11 1.502(4) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.503(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C2 N1 C15 125.0(3) . . ?
C2 N1 C12 125.0(3) . . ?
C15 N1 C12 109.9(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.2(3) . . ?
N1 C2 C1 118.6(3) . . ?
C3 C2 C1 122.1(3) . . ?
C4 C3 C2 124.1(3) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
C3 C4 C5 126.7(3) . . ?
C3 C4 H4 116.7 . . ?
C5 C4 H4 116.7 . . ?
C10 C5 C6 119.0(3) . . ?
C10 C5 C4 120.7(3) . . ?
C6 C5 C4 120.3(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C11 119.2(3) . . ?
C5 C6 C11 122.0(3) . . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 103.9(2) . . ?
N1 C12 H12A 111.0 . . ?
C13 C12 H12A 111.0 . . ?
N1 C12 H12B 111.0 . . ?
C13 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C12 C13 C14 104.0(3) . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
C14 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C13 C14 C15 103.2(3) . . ?
C13 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
N1 C15 C14 104.0(2) . . ?
N1 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
N1 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
F3 B1 F4 111.4(3) . . ?
F3 B1 F2 110.5(3) . . ?
F4 B1 F2 109.8(3) . . ?
F3 B1 F1 107.8(3) . . ?
F4 B1 F1 107.6(3) . . ?
F2 B1 F1 109.8(3) . . ?

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
C15 N1 C2 C3 4.3(5) . . . . ?
C12 N1 C2 C3 -177.3(3) . . . . ?
C15 N1 C2 C1 -177.6(3) . . . . ?
C12 N1 C2 C1 0.8(5) . . . . ?
N1 C2 C3 C4 179.7(3) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 -179.2(3) . . . . ?
C3 C4 C5 C10 -8.1(5) . . . . ?
C3 C4 C5 C6 171.4(3) . . . . ?
C10 C5 C6 C7 -0.8(5) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C10 C5 C6 C11 178.1(3) . . . . ?
C4 C5 C6 C11 -1.5(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C11 C6 C7 C8 -178.0(3) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C5 -0.4(5) . . . . ?
C6 C5 C10 C9 0.6(5) . . . . ?
C4 C5 C10 C9 -179.8(3) . . . . ?
C2 N1 C12 C13 168.1(3) . . . . ?
C15 N1 C12 C13 -13.3(3) . . . . ?
N1 C12 C13 C14 32.3(3) . . . . ?
C12 C13 C14 C15 -39.3(3) . . . . ?
C2 N1 C15 C14 167.8(3) . . . . ?
C12 N1 C15 C14 -10.9(3) . . . . ?
C13 C14 C15 N1 30.5(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_4-Me-PYRROIMINIUM-BF4-2
_audit_block_doi                 10.5517/ccdc.csd.cc2kl09h
_database_code_depnum_ccdc_archive 'CCDC 2370796'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C15 H20 B F4 N'
_chemical_formula_moiety         'C15 H20 B F4 N'
_chemical_formula_weight         301.13
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.1100(2)
_cell_length_b                   8.7342(2)
_cell_length_c                   16.7607(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.8200(15)
_cell_angle_gamma                90.0000
_cell_volume                     1479.87(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5385
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  0.944

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

_diffrn_ambient_temperature      123
_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            16192
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         4.374
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_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             2692
_reflns_number_gt                2164
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0833
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1790
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2692
_refine_ls_number_parameters     192
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0866P)²+1.5510P] 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          0.001
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.45
_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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.84802(17) 0.6665(2) 0.25628(10) 0.0422(5) Uani 1 1 d . . . . .
F2 F 0.68772(17) 0.5129(2) 0.30660(12) 0.0491(5) Uani 1 1 d . . . . .
F3 F 0.7163(3) 0.7542(2) 0.35403(16) 0.0756(8) Uani 1 1 d . . . . .
F4 F 0.86646(18) 0.5712(3) 0.38169(11) 0.0530(6) Uani 1 1 d . . . . .
N1 N 0.2766(2) 0.4937(2) 0.32189(12) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.1679(3) 0.3494(3) 0.42432(17) 0.0303(6) Uani 1 1 d . . . . .
H1A H 0.0971 0.4255 0.4193 0.036 Uiso 1 1 calc R U . . .
H1B H 0.1870 0.3300 0.4809 0.036 Uiso 1 1 calc R U . . .
H1C H 0.1399 0.2540 0.3984 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2898(3) 0.4086(3) 0.38507(15) 0.0247(6) Uani 1 1 d . . . . .
C3 C 0.4209(3) 0.3723(3) 0.41530(15) 0.0253(6) Uani 1 1 d . . . . .
H3 H 0.4946 0.4162 0.3892 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4446(3) 0.2801(3) 0.47815(15) 0.0253(6) Uani 1 1 d . . . . .
H4 H 0.3694 0.2400 0.5044 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5737(2) 0.2355(3) 0.51018(15) 0.0245(6) Uani 1 1 d . . . . .
C6 C 0.6934(3) 0.2962(3) 0.48215(16) 0.0261(6) Uani 1 1 d . . . . .
H6 H 0.6917 0.3728 0.4419 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8131(3) 0.2453(3) 0.51252(16) 0.0281(6) Uani 1 1 d . . . . .
H7 H 0.8928 0.2868 0.4923 0.034 Uiso 1 1 calc R U . . .
C8 C 0.8195(3) 0.1336(3) 0.57264(16) 0.0275(6) Uani 1 1 d . . . . .
C9 C 0.7010(3) 0.0756(3) 0.60120(16) 0.0293(6) Uani 1 1 d . . . . .
H9 H 0.7027 0.0002 0.6421 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5802(3) 0.1262(3) 0.57083(16) 0.0281(6) Uani 1 1 d . . . . .
H10 H 0.5006 0.0858 0.5917 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9501(3) 0.0794(3) 0.60509(19) 0.0356(7) Uani 1 1 d . . . . .
H11A H 0.9887 0.0057 0.5680 0.043 Uiso 1 1 calc R U . . .
H11B H 0.9373 0.0301 0.6569 0.043 Uiso 1 1 calc R U . . .
H11C H 1.0099 0.1670 0.6116 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1485(3) 0.5427(3) 0.28583(16) 0.0279(6) Uani 1 1 d . . . . .
H12A H 0.0886 0.5828 0.3271 0.034 Uiso 1 1 calc R U . . .
H12B H 0.1045 0.4564 0.2579 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1853(3) 0.6668(4) 0.2278(2) 0.0413(8) Uani 1 1 d . . . . .
H13A H 0.1220 0.6706 0.1823 0.050 Uiso 1 1 calc R U . . .
H13B H 0.1875 0.7681 0.2543 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3207(3) 0.6212(4) 0.20074(19) 0.0423(8) Uani 1 1 d . . . . .
H14A H 0.3700 0.7114 0.1814 0.051 Uiso 1 1 calc R U . . .
H14B H 0.3145 0.5447 0.1572 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3887(3) 0.5528(3) 0.27410(17) 0.0297(6) Uani 1 1 d . . . . .
H15A H 0.4494 0.4690 0.2591 0.036 Uiso 1 1 calc R U . . .
H15B H 0.4392 0.6317 0.3040 0.036 Uiso 1 1 calc R U . . .
B1 B 0.7780(3) 0.6273(4) 0.3237(2) 0.0306(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.385(3) . ?
F2 B1 1.380(4) . ?
F3 B1 1.373(4) . ?
F4 B1 1.400(4) . ?
N1 C2 1.299(3) . ?
N1 C12 1.485(3) . ?
N1 C15 1.489(3) . ?
C1 C2 1.497(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.447(4) . ?
C3 C4 1.345(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.458(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.395(4) . ?
C5 C6 1.408(4) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 C11 1.497(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.502(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C2 N1 C12 125.1(2) . . ?
C2 N1 C15 124.5(2) . . ?
C12 N1 C15 110.3(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 119.6(2) . . ?
N1 C2 C1 118.7(2) . . ?
C3 C2 C1 121.7(2) . . ?
C4 C3 C2 123.9(2) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 C5 126.7(2) . . ?
C3 C4 H4 116.7 . . ?
C5 C4 H4 116.7 . . ?
C10 C5 C6 118.0(2) . . ?
C10 C5 C4 118.9(2) . . ?
C6 C5 C4 123.1(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 C11 121.3(3) . . ?
C7 C8 C11 120.8(3) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 104.3(2) . . ?
N1 C12 H12A 110.9 . . ?
C13 C12 H12A 110.9 . . ?
N1 C12 H12B 110.9 . . ?
C13 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C14 C13 C12 103.8(2) . . ?
C14 C13 H13A 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C14 C13 H13B 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C13 C14 C15 105.3(2) . . ?
C13 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
N1 C15 C14 103.4(2) . . ?
N1 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
N1 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
F3 B1 F2 111.0(3) . . ?
F3 B1 F1 110.1(3) . . ?
F2 B1 F1 110.7(3) . . ?
F3 B1 F4 108.3(3) . . ?
F2 B1 F4 107.7(2) . . ?
F1 B1 F4 108.9(2) . . ?

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
C12 N1 C2 C3 -178.4(2) . . . . ?
C15 N1 C2 C3 3.2(4) . . . . ?
C12 N1 C2 C1 2.1(4) . . . . ?
C15 N1 C2 C1 -176.2(2) . . . . ?
N1 C2 C3 C4 -177.1(2) . . . . ?
C1 C2 C3 C4 2.3(4) . . . . ?
C2 C3 C4 C5 178.1(2) . . . . ?
C3 C4 C5 C10 -173.5(3) . . . . ?
C3 C4 C5 C6 5.7(4) . . . . ?
C10 C5 C6 C7 1.8(4) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C6 C7 C8 C11 -180.0(2) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C11 C8 C9 C10 -180.0(2) . . . . ?
C8 C9 C10 C5 0.7(4) . . . . ?
C6 C5 C10 C9 -1.8(4) . . . . ?
C4 C5 C10 C9 177.5(2) . . . . ?
C2 N1 C12 C13 166.9(3) . . . . ?
C15 N1 C12 C13 -14.5(3) . . . . ?
N1 C12 C13 C14 31.0(3) . . . . ?
C12 C13 C14 C15 -36.5(3) . . . . ?
C2 N1 C15 C14 170.9(2) . . . . ?
C12 N1 C15 C14 -7.7(3) . . . . ?
C13 C14 C15 N1 27.1(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_MEDMEIMINIUM-SYN-HT-DIMER-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0dl
_database_code_depnum_ccdc_archive 'CCDC 2370799'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_moiety         'C20 H20 O2'
_chemical_formula_weight         292.38
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.0741(4)
_cell_length_b                   13.3976(5)
_cell_length_c                   9.2157(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.370(3)
_cell_angle_gamma                90.0000
_cell_volume                     1012.31(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4265
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      68.13
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    0.959
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312.00
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.866

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

_diffrn_ambient_temperature      123
_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            10389
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         5.312
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3514
_reflns_number_gt                2626
_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          ?
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3514
_refine_ls_number_parameters     256
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0387P)²+0.0438P] 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          0.187
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0064(13)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)

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)
;

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

#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

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

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Tri-OMe-PYRROIMINIUM-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0ck
_database_code_depnum_ccdc_archive 'CCDC 2370798'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C17 H24 B F4 N O3'
_chemical_formula_moiety         'C17 H24 B F4 N O3'
_chemical_formula_weight         377.19
_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                   7.6902(3)
_cell_length_b                   9.9674(3)
_cell_length_c                   12.0352(4)
_cell_angle_alpha                94.287(2)
_cell_angle_beta                 96.2441(19)
_cell_angle_gamma                96.7987(19)
_cell_volume                     906.99(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3483
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396.00
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.902

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

_diffrn_ambient_temperature      123
_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            9485
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         3.709
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3237
_reflns_number_gt                2123
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0925
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1376
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     239
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0741P)²+0.0863P] 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         0.37
_refine_diff_density_min         -0.40
_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)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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)
;
O O 0.0492 0.0322
;
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_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
F1 F 0.7173(3) 1.35143(18) 0.75515(19) 0.0866(8) Uani 1 1 d . . . . .
F2 F 0.5030(3) 1.17551(19) 0.70923(16) 0.0798(7) Uani 1 1 d . . . . .
F3 F 0.6690(3) 1.19178(16) 0.87443(14) 0.0672(6) Uani 1 1 d . . . . .
F4 F 0.4780(3) 1.34306(18) 0.84521(16) 0.0673(6) Uani 1 1 d . . . . .
O1 O 0.8481(2) 0.33045(18) 0.13726(14) 0.0393(5) Uani 1 1 d . . . . .
O2 O 0.9611(2) 0.13713(16) 0.26322(14) 0.0363(5) Uani 1 1 d . . . . .
O3 O 0.9320(2) 0.14330(16) 0.48042(15) 0.0372(5) Uani 1 1 d . . . . .
N1 N 0.6548(3) 0.76143(19) 0.73614(16) 0.0273(5) Uani 1 1 d . . . . .
C1 C 0.6108(4) 0.8497(2) 0.5543(2) 0.0341(6) Uani 1 1 d . . . . .
H1A H 0.5363 0.8095 0.4859 0.041 Uiso 1 1 calc R U . . .
H1B H 0.7210 0.8965 0.5344 0.041 Uiso 1 1 calc R U . . .
H1C H 0.5485 0.9147 0.5945 0.041 Uiso 1 1 calc R U . . .
C2 C 0.6516(3) 0.7396(2) 0.6283(2) 0.0290(6) Uani 1 1 d . . . . .
C3 C 0.6944(3) 0.6125(2) 0.5803(2) 0.0305(6) Uani 1 1 d . . . . .
H3 H 0.7182 0.5447 0.6292 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7023(3) 0.5849(2) 0.4706(2) 0.0329(6) Uani 1 1 d . . . . .
H4 H 0.6682 0.6509 0.4224 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7584(3) 0.4629(2) 0.4176(2) 0.0308(6) Uani 1 1 d . . . . .
C6 C 0.7666(3) 0.4548(2) 0.3020(2) 0.0314(6) Uani 1 1 d . . . . .
H6 H 0.7291 0.5250 0.2595 0.038 Uiso 1 1 calc R U . . .
C7 C 0.8291(3) 0.3451(2) 0.2489(2) 0.0314(6) Uani 1 1 d . . . . .
C8 C 0.8827(3) 0.2403(2) 0.3110(2) 0.0322(6) Uani 1 1 d . . . . .
C9 C 0.8730(3) 0.2484(2) 0.4266(2) 0.0311(6) Uani 1 1 d . . . . .
C10 C 0.8114(3) 0.3578(2) 0.4801(2) 0.0305(6) Uani 1 1 d . . . . .
H10 H 0.8049 0.3620 0.5586 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8069(4) 0.4401(3) 0.0725(2) 0.0435(7) Uani 1 1 d . . . . .
H11A H 0.6836 0.4540 0.0764 0.052 Uiso 1 1 calc R U . . .
H11B H 0.8250 0.4181 -0.0058 0.052 Uiso 1 1 calc R U . . .
H11C H 0.8841 0.5231 0.1027 0.052 Uiso 1 1 calc R U . . .
C12 C 0.8477(4) 0.0396(3) 0.1854(3) 0.0523(8) Uani 1 1 d . . . . .
H12A H 0.9178 -0.0258 0.1527 0.063 Uiso 1 1 calc R U . . .
H12B H 0.7904 0.0864 0.1255 0.063 Uiso 1 1 calc R U . . .
H12C H 0.7577 -0.0084 0.2248 0.063 Uiso 1 1 calc R U . . .
C13 C 0.9402(4) 0.1536(3) 0.6002(2) 0.0413(7) Uani 1 1 d . . . . .
H13A H 0.9878 0.0743 0.6291 0.050 Uiso 1 1 calc R U . . .
H13B H 0.8216 0.1573 0.6218 0.050 Uiso 1 1 calc R U . . .
H13C H 1.0171 0.2363 0.6316 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7039(3) 0.6652(2) 0.8199(2) 0.0328(6) Uani 1 1 d . . . . .
H14A H 0.8123 0.6268 0.8036 0.039 Uiso 1 1 calc R U . . .
H14B H 0.6074 0.5900 0.8201 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7342(4) 0.7509(3) 0.9306(2) 0.0454(7) Uani 1 1 d . . . . .
H15A H 0.8586 0.7925 0.9470 0.054 Uiso 1 1 calc R U . . .
H15B H 0.7036 0.6961 0.9927 0.054 Uiso 1 1 calc R U . . .
C16 C 0.6125(4) 0.8579(3) 0.9145(2) 0.0446(7) Uani 1 1 d . . . . .
H16A H 0.6526 0.9392 0.9676 0.053 Uiso 1 1 calc R U . . .
H16B H 0.4903 0.8225 0.9255 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6232(4) 0.8910(2) 0.7945(2) 0.0344(6) Uani 1 1 d . . . . .
H17A H 0.5117 0.9203 0.7617 0.041 Uiso 1 1 calc R U . . .
H17B H 0.7214 0.9634 0.7902 0.041 Uiso 1 1 calc R U . . .
B1 B 0.5904(5) 1.2648(3) 0.7964(3) 0.0432(8) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.384(4) . ?
F2 B1 1.382(4) . ?
F3 B1 1.364(4) . ?
F4 B1 1.379(4) . ?
O1 C7 1.366(3) . ?
O1 C11 1.434(3) . ?
O2 C8 1.373(3) . ?
O2 C12 1.439(3) . ?
O3 C9 1.369(3) . ?
O3 C13 1.431(3) . ?
N1 C2 1.297(3) . ?
N1 C17 1.482(3) . ?
N1 C14 1.492(3) . ?
C1 C2 1.504(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.442(3) . ?
C3 C4 1.338(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.463(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 C10 1.407(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(3) . ?
C8 C9 1.398(4) . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.508(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.510(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C7 O1 C11 116.9(2) . . ?
C8 O2 C12 116.13(19) . . ?
C9 O3 C13 117.01(19) . . ?
C2 N1 C17 124.35(19) . . ?
C2 N1 C14 125.5(2) . . ?
C17 N1 C14 110.01(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 120.0(2) . . ?
N1 C2 C1 119.7(2) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C3 C2 123.5(2) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C3 C4 C5 126.3(2) . . ?
C3 C4 H4 116.8 . . ?
C5 C4 H4 116.8 . . ?
C6 C5 C10 119.7(2) . . ?
C6 C5 C4 118.1(2) . . ?
C10 C5 C4 122.1(2) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C6 124.7(2) . . ?
O1 C7 C8 115.2(2) . . ?
C6 C7 C8 120.1(2) . . ?
O2 C8 C9 118.9(2) . . ?
O2 C8 C7 121.4(2) . . ?
C9 C8 C7 119.3(2) . . ?
O3 C9 C10 124.0(2) . . ?
O3 C9 C8 115.1(2) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C5 119.7(2) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 104.20(19) . . ?
N1 C14 H14A 110.9 . . ?
C15 C14 H14A 110.9 . . ?
N1 C14 H14B 110.9 . . ?
C15 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C14 C15 C16 103.9(2) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 104.1(2) . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 109.0 . . ?
N1 C17 C16 103.78(19) . . ?
N1 C17 H17A 111.0 . . ?
C16 C17 H17A 111.0 . . ?
N1 C17 H17B 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
F3 B1 F4 110.0(3) . . ?
F3 B1 F2 108.4(2) . . ?
F4 B1 F2 112.0(3) . . ?
F3 B1 F1 109.7(3) . . ?
F4 B1 F1 107.8(2) . . ?
F2 B1 F1 109.0(3) . . ?

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
C17 N1 C2 C3 176.3(2) . . . . ?
C14 N1 C2 C3 1.3(4) . . . . ?
C17 N1 C2 C1 -1.0(3) . . . . ?
C14 N1 C2 C1 -176.0(2) . . . . ?
N1 C2 C3 C4 -176.7(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 174.7(2) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
C3 C4 C5 C10 0.2(4) . . . . ?
C10 C5 C6 C7 -1.0(4) . . . . ?
C4 C5 C6 C7 176.1(2) . . . . ?
C11 O1 C7 C6 2.8(4) . . . . ?
C11 O1 C7 C8 -175.6(2) . . . . ?
C5 C6 C7 O1 -177.5(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C12 O2 C8 C9 114.6(3) . . . . ?
C12 O2 C8 C7 -72.1(3) . . . . ?
O1 C7 C8 O2 4.9(3) . . . . ?
C6 C7 C8 O2 -173.6(2) . . . . ?
O1 C7 C8 C9 178.2(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C13 O3 C9 C10 -4.2(3) . . . . ?
C13 O3 C9 C8 174.2(2) . . . . ?
O2 C8 C9 O3 -5.0(3) . . . . ?
C7 C8 C9 O3 -178.5(2) . . . . ?
O2 C8 C9 C10 173.5(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
O3 C9 C10 C5 178.1(2) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C6 C5 C10 C9 0.8(4) . . . . ?
C4 C5 C10 C9 -176.2(2) . . . . ?
C2 N1 C14 C15 165.2(2) . . . . ?
C17 N1 C14 C15 -10.4(3) . . . . ?
N1 C14 C15 C16 29.7(3) . . . . ?
C14 C15 C16 C17 -38.2(3) . . . . ?
C2 N1 C17 C16 171.3(2) . . . . ?
C14 N1 C17 C16 -13.0(3) . . . . ?
C15 C16 C17 N1 31.3(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_PYRROIMINIUM-BF4-DIMER-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0fm
_database_code_depnum_ccdc_archive 'CCDC 2370800'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C28 H36 B2 F8 N2'
_chemical_formula_moiety         'C28 H36 B2 F8 N2'
_chemical_formula_weight         574.21
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1302(3)
_cell_length_b                   14.6918(5)
_cell_length_c                   13.1044(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.392(2)
_cell_angle_gamma                90.0000
_cell_volume                     1345.71(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5211
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600.00
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  0.902

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

_diffrn_ambient_temperature      123
_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            15256
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4732
_reflns_number_gt                3648
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.916

#==============================================================================
# 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          0.0579
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1241
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4732
_refine_ls_number_parameters     363
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0638P)²+0.3918P] 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          0.001
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(19)

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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.2809(7) 0.4185(3) -0.0348(4) 0.0711(15) Uani 1 1 d . . . . .
F2 F 0.4649(6) 0.3544(4) 0.0962(3) 0.0826(17) Uani 1 1 d . . . . .
F3 F 0.1846(6) 0.2862(3) 0.0291(3) 0.0424(10) Uani 1 1 d . . . . .
F4 F 0.4273(7) 0.2860(4) -0.0613(4) 0.0705(16) Uani 1 1 d . . . . .
F5 F 0.2741(7) -0.1277(4) 0.4608(5) 0.096(2) Uani 1 1 d . . . . .
F6 F 0.4752(6) -0.0582(4) 0.5963(3) 0.0757(16) Uani 1 1 d . . . . .
F7 F 0.4266(8) 0.0013(4) 0.4398(4) 0.0762(17) Uani 1 1 d . . . . .
F8 F 0.1842(6) 0.0022(3) 0.5288(3) 0.0426(10) Uani 1 1 d . . . . .
N1 N -0.2633(7) 0.7944(4) 0.5289(4) 0.0277(12) Uani 1 1 d . . . . .
N2 N 0.2586(8) 0.9930(4) 0.9698(4) 0.0312(13) Uani 1 1 d . . . . .
C1 C -0.0820(10) 0.8851(5) 0.6681(5) 0.0293(15) Uani 1 1 d . . . . .
H1 H -0.0614 0.9273 0.6114 0.035 Uiso 1 1 calc R U . . .
C2 C -0.1184(9) 0.9393(5) 0.7670(5) 0.0294(16) Uani 1 1 d . . . . .
H2 H -0.2266 0.9109 0.7938 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0813(9) 0.9013(5) 0.8305(5) 0.0311(15) Uani 1 1 d . . . . .
H3 H 0.0619 0.8586 0.8870 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1156(10) 0.8500(5) 0.7353(5) 0.0304(16) Uani 1 1 d . . . . .
H4 H 0.2236 0.8793 0.7092 0.036 Uiso 1 1 calc R U . . .
C5 C -0.2195(9) 0.8120(4) 0.6276(5) 0.0302(14) Uani 1 1 d . . . . .
C6 C -0.3052(9) 0.7540(5) 0.6998(5) 0.0360(16) Uani 1 1 d . . . . .
H6A H -0.2325 0.7616 0.7710 0.043 Uiso 1 1 calc R U . . .
H6B H -0.3011 0.6901 0.6791 0.043 Uiso 1 1 calc R U . . .
H6C H -0.4384 0.7723 0.6968 0.043 Uiso 1 1 calc R U . . .
C7 C -0.2032(11) 0.8502(5) 0.4448(5) 0.0369(17) Uani 1 1 d . . . . .
H7A H -0.0639 0.8448 0.4475 0.044 Uiso 1 1 calc R U . . .
H7B H -0.2360 0.9152 0.4511 0.044 Uiso 1 1 calc R U . . .
C8 C -0.3166(10) 0.8093(5) 0.3449(5) 0.0395(18) Uani 1 1 d . . . . .
H8A H -0.2453 0.8139 0.2876 0.047 Uiso 1 1 calc R U . . .
H8B H -0.4421 0.8398 0.3237 0.047 Uiso 1 1 calc R U . . .
C9 C -0.3412(10) 0.7103(6) 0.3743(5) 0.0378(17) Uani 1 1 d . . . . .
H9A H -0.4498 0.6817 0.3262 0.045 Uiso 1 1 calc R U . . .
H9B H -0.2236 0.6748 0.3732 0.045 Uiso 1 1 calc R U . . .
C10 C -0.3801(11) 0.7157(5) 0.4823(5) 0.0351(16) Uani 1 1 d . . . . .
H10A H -0.5177 0.7264 0.4809 0.042 Uiso 1 1 calc R U . . .
H10B H -0.3399 0.6592 0.5217 0.042 Uiso 1 1 calc R U . . .
C11 C -0.1442(10) 1.0400(5) 0.7602(5) 0.0305(17) Uani 1 1 d . . . . .
C12 C -0.1717(11) 1.0837(6) 0.8519(5) 0.0384(18) Uani 1 1 d . . . . .
H12 H -0.1817 1.0488 0.9116 0.046 Uiso 1 1 calc R U . . .
C13 C -0.1841(12) 1.1780(6) 0.8545(6) 0.050(2) Uani 1 1 d . . . . .
H13 H -0.2012 1.2071 0.9167 0.059 Uiso 1 1 calc R U . . .
C14 C -0.1720(12) 1.2302(6) 0.7688(6) 0.050(2) Uani 1 1 d . . . . .
H14 H -0.1803 1.2947 0.7720 0.060 Uiso 1 1 calc R U . . .
C15 C -0.1480(11) 1.1883(5) 0.6789(6) 0.0410(19) Uani 1 1 d . . . . .
H15 H -0.1390 1.2236 0.6193 0.049 Uiso 1 1 calc R U . . .
C16 C -0.1369(11) 1.0936(6) 0.6752(6) 0.0371(18) Uani 1 1 d . . . . .
H16 H -0.1239 1.0652 0.6118 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2216(9) 0.9762(5) 0.8725(5) 0.0299(15) Uani 1 1 d . . . . .
C18 C 0.3053(9) 1.0344(5) 0.8007(5) 0.0358(16) Uani 1 1 d . . . . .
H18A H 0.2645 1.0121 0.7292 0.043 Uiso 1 1 calc R U . . .
H18B H 0.4452 1.0323 0.8202 0.043 Uiso 1 1 calc R U . . .
H18C H 0.2617 1.0972 0.8051 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3812(11) 1.0714(5) 1.0159(5) 0.0344(17) Uani 1 1 d . . . . .
H19A H 0.3440 1.1282 0.9763 0.041 Uiso 1 1 calc R U . . .
H19B H 0.5182 1.0590 1.0174 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3411(11) 1.0781(6) 1.1262(5) 0.0399(18) Uani 1 1 d . . . . .
H20A H 0.4500 1.1060 1.1747 0.048 Uiso 1 1 calc R U . . .
H20B H 0.2239 1.1139 1.1272 0.048 Uiso 1 1 calc R U . . .
C21 C 0.3150(10) 0.9792(6) 1.1538(5) 0.0415(19) Uani 1 1 d . . . . .
H21A H 0.2436 0.9743 1.2111 0.050 Uiso 1 1 calc R U . . .
H21B H 0.4404 0.9486 1.1750 0.050 Uiso 1 1 calc R U . . .
C22 C 0.2009(10) 0.9373(5) 1.0534(5) 0.0330(15) Uani 1 1 d . . . . .
H22A H 0.2350 0.8725 1.0472 0.040 Uiso 1 1 calc R U . . .
H22B H 0.0615 0.9420 1.0510 0.040 Uiso 1 1 calc R U . . .
C23 C 0.1445(10) 0.7469(5) 0.7387(5) 0.0316(17) Uani 1 1 d . . . . .
C24 C 0.1344(11) 0.6946(5) 0.8271(6) 0.0338(16) Uani 1 1 d . . . . .
H24 H 0.1176 0.7231 0.8898 0.041 Uiso 1 1 calc R U . . .
C25 C 0.1492(10) 0.6009(6) 0.8216(6) 0.0414(19) Uani 1 1 d . . . . .
H25 H 0.1438 0.5654 0.8816 0.050 Uiso 1 1 calc R U . . .
C26 C 0.1717(11) 0.5577(6) 0.7317(6) 0.046(2) Uani 1 1 d . . . . .
H26 H 0.1772 0.4932 0.7291 0.055 Uiso 1 1 calc R U . . .
C27 C 0.1864(12) 0.6095(6) 0.6442(6) 0.048(2) Uani 1 1 d . . . . .
H27 H 0.2059 0.5810 0.5821 0.058 Uiso 1 1 calc R U . . .
C28 C 0.1720(11) 0.7031(6) 0.6499(5) 0.0377(18) Uani 1 1 d . . . . .
H28 H 0.1815 0.7385 0.5905 0.045 Uiso 1 1 calc R U . . .
B1 B 0.3356(13) 0.3349(6) 0.0035(7) 0.038(2) Uani 1 1 d . . . . .
B2 B 0.3412(13) -0.0460(7) 0.5066(7) 0.039(2) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 B1 1.355(10) . ?
F2 B1 1.402(10) . ?
F3 B1 1.388(10) . ?
F4 B1 1.372(9) . ?
F5 B2 1.384(10) . ?
F6 B2 1.373(10) . ?
F7 B2 1.352(10) . ?
F8 B2 1.403(9) . ?
N1 C5 1.296(8) . ?
N1 C10 1.483(9) . ?
N1 C7 1.502(8) . ?
N2 C17 1.274(8) . ?
N2 C22 1.490(9) . ?
N2 C19 1.500(10) . ?
C1 C5 1.480(9) . ?
C1 C2 1.585(8) . ?
C1 C4 1.593(9) . ?
C1 H1 1.0000 . ?
C2 C11 1.492(10) . ?
C2 C3 1.602(8) . ?
C2 H2 1.0000 . ?
C3 C17 1.516(9) . ?
C3 C4 1.518(9) . ?
C3 H3 1.0000 . ?
C4 C23 1.529(10) . ?
C4 H4 1.0000 . ?
C5 C6 1.492(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.520(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.523(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.497(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.372(10) . ?
C11 C12 1.410(9) . ?
C12 C13 1.390(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.481(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.531(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(12) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.532(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.377(10) . ?
C23 C24 1.404(10) . ?
C24 C25 1.384(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(12) . ?
C27 H27 0.9500 . ?
C28 H28 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
C5 N1 C10 124.8(6) . . ?
C5 N1 C7 125.2(6) . . ?
C10 N1 C7 110.0(5) . . ?
C17 N2 C22 126.7(6) . . ?
C17 N2 C19 122.8(6) . . ?
C22 N2 C19 110.4(5) . . ?
C5 C1 C2 117.0(6) . . ?
C5 C1 C4 114.5(6) . . ?
C2 C1 C4 88.9(4) . . ?
C5 C1 H1 111.6 . . ?
C2 C1 H1 111.6 . . ?
C4 C1 H1 111.6 . . ?
C11 C2 C1 119.2(6) . . ?
C11 C2 C3 117.6(6) . . ?
C1 C2 C3 88.7(5) . . ?
C11 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C17 C3 C4 117.2(6) . . ?
C17 C3 C2 113.0(6) . . ?
C4 C3 C2 90.9(4) . . ?
C17 C3 H3 111.4 . . ?
C4 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C3 C4 C23 120.7(6) . . ?
C3 C4 C1 91.5(5) . . ?
C23 C4 C1 115.9(6) . . ?
C3 C4 H4 109.2 . . ?
C23 C4 H4 109.2 . . ?
C1 C4 H4 109.2 . . ?
N1 C5 C1 121.0(6) . . ?
N1 C5 C6 118.1(6) . . ?
C1 C5 C6 120.8(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 103.6(6) . . ?
N1 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
N1 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C7 C8 C9 103.2(6) . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 103.9(6) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
N1 C10 C9 103.7(6) . . ?
N1 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
N1 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C16 C11 C12 117.7(7) . . ?
C16 C11 C2 126.4(7) . . ?
C12 C11 C2 115.9(6) . . ?
C13 C12 C11 119.6(8) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 121.4(8) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.3(8) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.7(7) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 122.1(8) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
N2 C17 C18 119.6(6) . . ?
N2 C17 C3 119.7(6) . . ?
C18 C17 C3 120.6(5) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C20 103.1(6) . . ?
N2 C19 H19A 111.1 . . ?
C20 C19 H19A 111.1 . . ?
N2 C19 H19B 111.1 . . ?
C20 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
C21 C20 C19 102.6(6) . . ?
C21 C20 H20A 111.2 . . ?
C19 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
C19 C20 H20B 111.2 . . ?
H20A C20 H20B 109.2 . . ?
C20 C21 C22 104.5(6) . . ?
C20 C21 H21A 110.9 . . ?
C22 C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
N2 C22 C21 103.5(6) . . ?
N2 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
N2 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.0 . . ?
C28 C23 C24 118.7(7) . . ?
C28 C23 C4 118.7(6) . . ?
C24 C23 C4 122.5(7) . . ?
C25 C24 C23 119.0(7) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C24 121.8(7) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 119.5(8) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C28 C27 C26 118.6(8) . . ?
C28 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C23 C28 C27 122.3(8) . . ?
C23 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
F1 B1 F4 112.5(7) . . ?
F1 B1 F3 112.1(7) . . ?
F4 B1 F3 111.5(7) . . ?
F1 B1 F2 103.2(7) . . ?
F4 B1 F2 109.3(7) . . ?
F3 B1 F2 107.7(6) . . ?
F7 B2 F6 107.2(7) . . ?
F7 B2 F5 109.1(7) . . ?
F6 B2 F5 112.4(8) . . ?
F7 B2 F8 110.8(8) . . ?
F6 B2 F8 109.7(6) . . ?
F5 B2 F8 107.8(7) . . ?

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
C5 C1 C2 C11 -122.0(7) . . . . ?
C4 C1 C2 C11 121.0(5) . . . . ?
C5 C1 C2 C3 116.7(5) . . . . ?
C4 C1 C2 C3 -0.3(7) . . . . ?
C11 C2 C3 C17 -2.1(8) . . . . ?
C1 C2 C3 C17 120.5(5) . . . . ?
C11 C2 C3 C4 -122.3(5) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C17 C3 C4 C23 121.6(7) . . . . ?
C2 C3 C4 C23 -121.8(6) . . . . ?
C17 C3 C4 C1 -116.9(5) . . . . ?
C2 C3 C4 C1 -0.3(7) . . . . ?
C5 C1 C4 C3 -119.0(5) . . . . ?
C2 C1 C4 C3 0.3(7) . . . . ?
C5 C1 C4 C23 6.4(9) . . . . ?
C2 C1 C4 C23 125.8(5) . . . . ?
C10 N1 C5 C1 172.1(6) . . . . ?
C7 N1 C5 C1 -7.8(10) . . . . ?
C10 N1 C5 C6 -5.4(10) . . . . ?
C7 N1 C5 C6 174.7(6) . . . . ?
C2 C1 C5 N1 146.5(6) . . . . ?
C4 C1 C5 N1 -111.6(7) . . . . ?
C2 C1 C5 C6 -36.1(8) . . . . ?
C4 C1 C5 C6 65.9(8) . . . . ?
C5 N1 C7 C8 -171.4(7) . . . . ?
C10 N1 C7 C8 8.7(7) . . . . ?
N1 C7 C8 C9 -29.4(7) . . . . ?
C7 C8 C9 C10 40.0(7) . . . . ?
C5 N1 C10 C9 -164.0(6) . . . . ?
C7 N1 C10 C9 15.9(7) . . . . ?
C8 C9 C10 N1 -34.2(7) . . . . ?
C1 C2 C11 C16 -1.1(11) . . . . ?
C3 C2 C11 C16 104.2(8) . . . . ?
C1 C2 C11 C12 -178.6(6) . . . . ?
C3 C2 C11 C12 -73.4(9) . . . . ?
C16 C11 C12 C13 -2.1(12) . . . . ?
C2 C11 C12 C13 175.7(8) . . . . ?
C11 C12 C13 C14 0.7(15) . . . . ?
C12 C13 C14 C15 0.2(14) . . . . ?
C13 C14 C15 C16 0.3(13) . . . . ?
C12 C11 C16 C15 2.6(11) . . . . ?
C2 C11 C16 C15 -174.9(8) . . . . ?
C14 C15 C16 C11 -1.8(13) . . . . ?
C22 N2 C17 C18 -174.4(6) . . . . ?
C19 N2 C17 C18 1.5(10) . . . . ?
C22 N2 C17 C3 10.0(10) . . . . ?
C19 N2 C17 C3 -174.2(6) . . . . ?
C4 C3 C17 N2 -148.3(7) . . . . ?
C2 C3 C17 N2 108.0(7) . . . . ?
C4 C3 C17 C18 36.1(9) . . . . ?
C2 C3 C17 C18 -67.7(8) . . . . ?
C17 N2 C19 C20 165.8(6) . . . . ?
C22 N2 C19 C20 -17.7(7) . . . . ?
N2 C19 C20 C21 35.0(7) . . . . ?
C19 C20 C21 C22 -40.0(7) . . . . ?
C17 N2 C22 C21 169.6(7) . . . . ?
C19 N2 C22 C21 -6.7(7) . . . . ?
C20 C21 C22 N2 28.9(7) . . . . ?
C3 C4 C23 C28 179.0(6) . . . . ?
C1 C4 C23 C28 70.2(9) . . . . ?
C3 C4 C23 C24 2.3(11) . . . . ?
C1 C4 C23 C24 -106.5(7) . . . . ?
C28 C23 C24 C25 -1.1(11) . . . . ?
C4 C23 C24 C25 175.6(8) . . . . ?
C23 C24 C25 C26 -0.6(13) . . . . ?
C24 C25 C26 C27 2.2(12) . . . . ?
C25 C26 C27 C28 -1.9(13) . . . . ?
C24 C23 C28 C27 1.3(12) . . . . ?
C4 C23 C28 C27 -175.6(8) . . . . ?
C26 C27 C28 C23 0.2(14) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_MEDMEIMINIUM-SYN-HT-DIMER-1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0jq
_database_code_depnum_ccdc_archive 'CCDC 2370803'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C26 H26 O2'
_chemical_formula_moiety         'C26 H26 O2'
_chemical_formula_weight         370.49
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.0741(4)
_cell_length_b                   13.3976(5)
_cell_length_c                   9.2157(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.370(3)
_cell_angle_gamma                90.0000
_cell_volume                     1012.31(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4265
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      68.13
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396.00
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.839

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

_diffrn_ambient_temperature      123
_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            10456
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         5.312
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3529
_reflns_number_gt                2640
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.927

#==============================================================================
# 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          0.0571
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0908
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3529
_refine_ls_number_parameters     256
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0264P)²+0.2132P] 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          0.262
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)

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)
;

#==============================================================================
# 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_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
O1 O 0.0727(6) 0.3374(4) 0.3055(6) 0.0340(12) Uani 1 1 d . . . . .
O2 O 0.4290(6) -0.0202(4) 0.6973(6) 0.0342(12) Uani 1 1 d . . . . .
C1 C 0.1793(8) 0.2192(5) 0.5204(7) 0.0233(16) Uani 1 1 d . . . . .
H1 H 0.1994 0.2368 0.6328 0.028 Uiso 1 1 calc R U . . .
C2 C 0.3415(8) 0.2139(6) 0.5048(7) 0.0250(17) Uani 1 1 d . . . . .
H2 H 0.3296 0.2458 0.4022 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3232(8) 0.0983(6) 0.4847(7) 0.0244(16) Uani 1 1 d . . . . .
H3 H 0.3055 0.0800 0.3732 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1562(8) 0.1010(5) 0.4930(7) 0.0222(15) Uani 1 1 d . . . . .
H4 H 0.1660 0.0679 0.5941 0.027 Uiso 1 1 calc R U . . .
C5 C 0.0482(9) 0.2852(5) 0.4017(8) 0.0270(17) Uani 1 1 d . . . . .
C6 C -0.1127(9) 0.2861(6) 0.4099(9) 0.0344(18) Uani 1 1 d . . . . .
H6A H -0.1004 0.3178 0.5103 0.041 Uiso 1 1 calc R U . . .
H6B H -0.1513 0.2174 0.4062 0.041 Uiso 1 1 calc R U . . .
H6C H -0.1918 0.3237 0.3186 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4910(8) 0.2541(5) 0.6451(7) 0.0227(15) Uani 1 1 d . . . . .
C8 C 0.6054(9) 0.3089(5) 0.6183(9) 0.0284(18) Uani 1 1 d . . . . .
H8 H 0.5896 0.3222 0.5114 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7456(9) 0.3453(6) 0.7483(9) 0.0354(18) Uani 1 1 d . . . . .
H9 H 0.8234 0.3838 0.7291 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7694(9) 0.3248(6) 0.9034(8) 0.0345(19) Uani 1 1 d . . . . .
H10 H 0.8644 0.3484 0.9916 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6571(10) 0.2709(7) 0.9294(8) 0.0293(18) Uani 1 1 d . . . . .
H11 H 0.6746 0.2572 1.0367 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5172(9) 0.2352(5) 0.8042(8) 0.0282(17) Uani 1 1 d . . . . .
H12 H 0.4396 0.1982 0.8258 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4539(8) 0.0315(6) 0.6029(8) 0.0257(16) Uani 1 1 d . . . . .
C14 C 0.6144(9) 0.0310(6) 0.5910(9) 0.0358(19) Uani 1 1 d . . . . .
H14A H 0.6716 -0.0318 0.6344 0.043 Uiso 1 1 calc R U . . .
H14B H 0.6814 0.0871 0.6527 0.043 Uiso 1 1 calc R U . . .
H14C H 0.5947 0.0375 0.4782 0.043 Uiso 1 1 calc R U . . .
C15 C 0.0092(8) 0.0621(5) 0.3537(8) 0.0231(15) Uani 1 1 d . . . . .
C16 C -0.0171(8) 0.0816(5) 0.1967(7) 0.0242(16) Uani 1 1 d . . . . .
H16 H 0.0607 0.1199 0.1772 0.029 Uiso 1 1 calc R U . . .
C17 C -0.1547(10) 0.0462(7) 0.0673(9) 0.0323(19) Uani 1 1 d . . . . .
H17 H -0.1704 0.0598 -0.0395 0.039 Uiso 1 1 calc R U . . .
C18 C -0.2703(9) -0.0097(5) 0.0959(9) 0.0338(19) Uani 1 1 d . . . . .
H18 H -0.3652 -0.0341 0.0086 0.041 Uiso 1 1 calc R U . . .
C19 C -0.2450(9) -0.0289(6) 0.2521(8) 0.0314(17) Uani 1 1 d . . . . .
H19 H -0.3233 -0.0665 0.2719 0.038 Uiso 1 1 calc R U . . .
C20 C -0.1081(9) 0.0057(6) 0.3788(9) 0.0275(17) Uani 1 1 d . . . . .
H20 H -0.0924 -0.0087 0.4854 0.033 Uiso 1 1 calc R U . . .
C21 C 1.1722(10) 0.2506(6) 0.9644(9) 0.036(2) Uani 1 1 d . . . . .
H21 H 1.1176 0.3131 0.9404 0.043 Uiso 1 1 calc R U . . .
C22 C 1.3291(10) 0.2436(6) 1.0861(9) 0.0359(19) Uani 1 1 d . . . . .
H22 H 1.3832 0.3013 1.1446 0.043 Uiso 1 1 calc R U . . .
C23 C 1.4062(10) 0.1513(7) 1.1215(9) 0.038(2) Uani 1 1 d . . . . .
H23 H 1.5125 0.1451 1.2064 0.045 Uiso 1 1 calc R U . . .
C24 C 1.3274(11) 0.0681(6) 1.0321(10) 0.039(2) Uani 1 1 d . . . . .
H24 H 1.3806 0.0051 1.0553 0.047 Uiso 1 1 calc R U . . .
C25 C 1.1741(11) 0.0761(6) 0.9114(9) 0.036(2) Uani 1 1 d . . . . .
H25 H 1.1216 0.0189 0.8501 0.043 Uiso 1 1 calc R U . . .
C26 C 1.0954(10) 0.1667(7) 0.8782(9) 0.037(2) Uani 1 1 d . . . . .
H26 H 0.9876 0.1716 0.7955 0.044 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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 C5 1.222(9) . ?
O2 C13 1.207(9) . ?
C1 C5 1.510(9) . ?
C1 C2 1.540(12) . ?
C1 C4 1.603(10) . ?
C1 H1 1.0000 . ?
C2 C7 1.517(8) . ?
C2 C3 1.561(11) . ?
C2 H2 1.0000 . ?
C3 C13 1.512(10) . ?
C3 C4 1.550(11) . ?
C3 H3 1.0000 . ?
C4 C15 1.494(9) . ?
C4 H4 1.0000 . ?
C5 C6 1.493(10) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.377(10) . ?
C7 C12 1.405(9) . ?
C8 C9 1.410(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.352(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.507(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.387(9) . ?
C15 C20 1.403(10) . ?
C16 C17 1.389(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(10) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.381(12) . ?
C21 C22 1.387(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.363(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(12) . ?
C25 H25 0.9500 . ?
C26 H26 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
C5 C1 C2 116.6(6) . . ?
C5 C1 C4 117.1(5) . . ?
C2 C1 C4 90.3(6) . . ?
C5 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C4 C1 H1 110.5 . . ?
C7 C2 C1 116.5(6) . . ?
C7 C2 C3 117.7(6) . . ?
C1 C2 C3 90.0(6) . . ?
C7 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C13 C3 C4 117.4(6) . . ?
C13 C3 C2 119.4(6) . . ?
C4 C3 C2 91.6(6) . . ?
C13 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C15 C4 C3 118.8(6) . . ?
C15 C4 C1 119.2(6) . . ?
C3 C4 C1 88.0(5) . . ?
C15 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C1 C4 H4 109.7 . . ?
O1 C5 C6 121.2(6) . . ?
O1 C5 C1 121.9(7) . . ?
C6 C5 C1 116.9(6) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.7(6) . . ?
C8 C7 C2 120.3(6) . . ?
C12 C7 C2 121.0(6) . . ?
C7 C8 C9 120.5(7) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.7(8) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.7(7) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.9(7) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C7 119.5(7) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.3 . . ?
O2 C13 C14 122.4(6) . . ?
O2 C13 C3 121.8(7) . . ?
C14 C13 C3 115.8(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.1(6) . . ?
C16 C15 C4 121.4(6) . . ?
C20 C15 C4 120.5(6) . . ?
C15 C16 C17 121.4(7) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 119.4(7) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 119.5(7) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.7(7) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 121.1(7) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.4 . . ?
C26 C21 C22 120.1(8) . . ?
C26 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.2(8) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C22 119.7(8) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 120.5(8) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.1(8) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.3(7) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.8 . . ?

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
C5 C1 C2 C7 115.9(7) . . . . ?
C4 C1 C2 C7 -123.3(6) . . . . ?
C5 C1 C2 C3 -122.9(5) . . . . ?
C4 C1 C2 C3 -2.1(6) . . . . ?
C7 C2 C3 C13 -0.6(11) . . . . ?
C1 C2 C3 C13 -120.8(6) . . . . ?
C7 C2 C3 C4 122.3(6) . . . . ?
C1 C2 C3 C4 2.1(7) . . . . ?
C13 C3 C4 C15 -114.9(7) . . . . ?
C2 C3 C4 C15 120.5(6) . . . . ?
C13 C3 C4 C1 122.5(5) . . . . ?
C2 C3 C4 C1 -2.0(6) . . . . ?
C5 C1 C4 C15 0.2(10) . . . . ?
C2 C1 C4 C15 -120.1(5) . . . . ?
C5 C1 C4 C3 122.4(6) . . . . ?
C2 C1 C4 C3 2.1(6) . . . . ?
C2 C1 C5 O1 -5.1(10) . . . . ?
C4 C1 C5 O1 -110.3(8) . . . . ?
C2 C1 C5 C6 176.6(6) . . . . ?
C4 C1 C5 C6 71.3(8) . . . . ?
C1 C2 C7 C8 -139.9(7) . . . . ?
C3 C2 C7 C8 115.0(8) . . . . ?
C1 C2 C7 C12 41.1(10) . . . . ?
C3 C2 C7 C12 -64.0(10) . . . . ?
C12 C7 C8 C9 -0.2(11) . . . . ?
C2 C7 C8 C9 -179.2(7) . . . . ?
C7 C8 C9 C10 0.9(12) . . . . ?
C8 C9 C10 C11 -0.8(13) . . . . ?
C9 C10 C11 C12 0.0(13) . . . . ?
C10 C11 C12 C7 0.7(12) . . . . ?
C8 C7 C12 C11 -0.6(11) . . . . ?
C2 C7 C12 C11 178.4(7) . . . . ?
C4 C3 C13 O2 2.1(10) . . . . ?
C2 C3 C13 O2 111.2(8) . . . . ?
C4 C3 C13 C14 -180.0(6) . . . . ?
C2 C3 C13 C14 -70.8(8) . . . . ?
C3 C4 C15 C16 -41.1(10) . . . . ?
C1 C4 C15 C16 64.2(10) . . . . ?
C3 C4 C15 C20 139.9(7) . . . . ?
C1 C4 C15 C20 -114.8(8) . . . . ?
C20 C15 C16 C17 -0.3(11) . . . . ?
C4 C15 C16 C17 -179.3(7) . . . . ?
C15 C16 C17 C18 0.5(12) . . . . ?
C16 C17 C18 C19 -0.2(12) . . . . ?
C17 C18 C19 C20 -0.3(12) . . . . ?
C18 C19 C20 C15 0.5(12) . . . . ?
C16 C15 C20 C19 -0.2(12) . . . . ?
C4 C15 C20 C19 178.8(7) . . . . ?
C26 C21 C22 C23 -1.0(11) . . . . ?
C21 C22 C23 C24 1.7(10) . . . . ?
C22 C23 C24 C25 -0.9(11) . . . . ?
C23 C24 C25 C26 -0.7(11) . . . . ?
C24 C25 C26 C21 1.4(10) . . . . ?
C22 C21 C26 C25 -0.5(10) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_IMINIUM-DIMER-NaBH4-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0gn
_database_code_depnum_ccdc_archive 'CCDC 2370801'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C28 H36 F2 N2'
_chemical_formula_moiety         'C28 H36 F2 N2'
_chemical_formula_weight         438.60
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.36553(17)
_cell_length_b                   10.40596(19)
_cell_length_c                   12.2778(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.9106(11)
_cell_angle_gamma                90.0000
_cell_volume                     1178.71(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4906
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472.00
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.906

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

_diffrn_ambient_temperature      123
_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            13488
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         3.655
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4206
_reflns_number_gt                3518
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.951

#==============================================================================
# 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          0.0437
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0926
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     292
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0515P)²+0.2091P] 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          0.001
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(19)

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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
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_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
F31 F 0.7663(3) 0.4658(4) 0.6984(2) 0.0375(9) Uani 1 1 d . . . . .
F32 F 1.2358(3) 0.1590(3) -0.1978(2) 0.0355(8) Uani 1 1 d . . . . .
N29 N 0.6991(4) 0.3093(4) 0.0689(3) 0.0209(9) Uani 1 1 d . . . . .
N30 N 1.3016(4) 0.3129(4) 0.4308(3) 0.0175(8) Uani 1 1 d . . . . .
C1 C 0.9923(4) 0.2729(5) 0.3332(3) 0.0187(11) Uani 1 1 d . . . . .
H1 H 1.0458 0.1916 0.3567 0.022 Uiso 1 1 calc R U . . .
C2 C 0.9028(5) 0.2547(5) 0.2128(3) 0.0183(10) Uani 1 1 d . . . . .
H2 H 0.9181 0.1657 0.1864 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0081(4) 0.3497(5) 0.1662(3) 0.0169(10) Uani 1 1 d . . . . .
H3 H 0.9553 0.4312 0.1424 0.020 Uiso 1 1 calc R U . . .
C4 C 1.0949(4) 0.3666(5) 0.2872(3) 0.0171(10) Uani 1 1 d . . . . .
H4 H 1.0788 0.4554 0.3137 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9212(5) 0.3215(5) 0.4271(4) 0.0173(10) Uani 1 1 d . . . . .
C6 C 0.8586(4) 0.4465(5) 0.4252(4) 0.0189(11) Uani 1 1 d . . . . .
H6 H 0.8535 0.4985 0.3610 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8055(5) 0.4928(5) 0.5155(3) 0.0216(11) Uani 1 1 d . . . . .
H7 H 0.7627 0.5757 0.5136 0.026 Uiso 1 1 calc R U . . .
C8 C 0.8151(5) 0.4178(6) 0.6076(4) 0.0273(12) Uani 1 1 d . . . . .
C9 C 0.8721(5) 0.2971(6) 0.6140(4) 0.0305(13) Uani 1 1 d . . . . .
H9 H 0.8756 0.2466 0.6789 0.037 Uiso 1 1 calc R U . . .
C10 C 0.9258(4) 0.2494(5) 0.5215(3) 0.0218(11) Uani 1 1 d . . . . .
H10 H 0.9662 0.1655 0.5244 0.026 Uiso 1 1 calc R U . . .
C11 C 0.7444(5) 0.2864(5) 0.1886(4) 0.0189(11) Uani 1 1 d . . . . .
H11 H 0.7301 0.3683 0.2279 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6568(5) 0.1804(5) 0.2362(3) 0.0236(12) Uani 1 1 d . . . . .
H12A H 0.6685 0.0987 0.1990 0.028 Uiso 1 1 calc R U . . .
H12B H 0.5540 0.2041 0.2240 0.028 Uiso 1 1 calc R U . . .
H12C H 0.6924 0.1713 0.3157 0.028 Uiso 1 1 calc R U . . .
C13 C 1.0776(5) 0.2997(5) 0.0734(4) 0.0193(10) Uani 1 1 d . . . . .
C14 C 1.0743(4) 0.3750(5) -0.0230(3) 0.0229(11) Uani 1 1 d . . . . .
H14 H 1.0350 0.4593 -0.0250 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1262(5) 0.3298(5) -0.1137(4) 0.0233(11) Uani 1 1 d . . . . .
H15 H 1.1219 0.3811 -0.1782 0.028 Uiso 1 1 calc R U . . .
C16 C 1.1851(5) 0.2071(6) -0.1084(4) 0.0223(11) Uani 1 1 d . . . . .
C17 C 1.1943(5) 0.1304(5) -0.0155(3) 0.0241(12) Uani 1 1 d . . . . .
H17 H 1.2363 0.0471 -0.0132 0.029 Uiso 1 1 calc R U . . .
C18 C 1.1395(4) 0.1801(5) 0.0750(3) 0.0204(11) Uani 1 1 d . . . . .
H18 H 1.1453 0.1291 0.1398 0.025 Uiso 1 1 calc R U . . .
C19 C 1.2590(5) 0.3359(5) 0.3122(4) 0.0193(12) Uani 1 1 d . . . . .
H19 H 1.2734 0.2533 0.2738 0.023 Uiso 1 1 calc R U . . .
C20 C 1.3431(5) 0.4388(6) 0.2620(4) 0.0265(12) Uani 1 1 d . . . . .
H20A H 1.3178 0.5236 0.2877 0.032 Uiso 1 1 calc R U . . .
H20B H 1.3184 0.4351 0.1812 0.032 Uiso 1 1 calc R U . . .
H20C H 1.4473 0.4241 0.2848 0.032 Uiso 1 1 calc R U . . .
C21 C 0.5544(4) 0.3655(5) 0.0349(3) 0.0230(11) Uani 1 1 d . . . . .
H21A H 0.5500 0.4539 0.0639 0.028 Uiso 1 1 calc R U . . .
H21B H 0.4789 0.3124 0.0605 0.028 Uiso 1 1 calc R U . . .
C22 C 0.5371(5) 0.3652(6) -0.0891(4) 0.0299(13) Uani 1 1 d . . . . .
H22A H 0.4338 0.3556 -0.1230 0.036 Uiso 1 1 calc R U . . .
H22B H 0.5745 0.4461 -0.1160 0.036 Uiso 1 1 calc R U . . .
C23 C 0.6240(5) 0.2522(6) -0.1166(4) 0.0378(15) Uani 1 1 d . . . . .
H23A H 0.6946 0.2791 -0.1636 0.045 Uiso 1 1 calc R U . . .
H23B H 0.5597 0.1856 -0.1565 0.045 Uiso 1 1 calc R U . . .
C24 C 0.7025(5) 0.2003(5) -0.0057(3) 0.0244(11) Uani 1 1 d . . . . .
H24A H 0.6510 0.1252 0.0184 0.029 Uiso 1 1 calc R U . . .
H24B H 0.8033 0.1754 -0.0101 0.029 Uiso 1 1 calc R U . . .
C25 C 1.4469(5) 0.2599(5) 0.4636(3) 0.0239(11) Uani 1 1 d . . . . .
H25A H 1.5212 0.3165 0.4404 0.029 Uiso 1 1 calc R U . . .
H25B H 1.4545 0.1731 0.4322 0.029 Uiso 1 1 calc R U . . .
C26 C 1.4624(5) 0.2550(6) 0.5910(3) 0.0244(12) Uani 1 1 d . . . . .
H26A H 1.5653 0.2609 0.6267 0.029 Uiso 1 1 calc R U . . .
H26B H 1.4202 0.1750 0.6154 0.029 Uiso 1 1 calc R U . . .
C27 C 1.3750(5) 0.3758(5) 0.6179(4) 0.0304(13) Uani 1 1 d . . . . .
H27A H 1.3040 0.3522 0.6656 0.036 Uiso 1 1 calc R U . . .
H27B H 1.4409 0.4425 0.6558 0.036 Uiso 1 1 calc R U . . .
C28 C 1.2974(5) 0.4241(6) 0.5047(3) 0.0263(12) Uani 1 1 d . . . . .
H28A H 1.1962 0.4492 0.5079 0.032 Uiso 1 1 calc R U . . .
H28B H 1.3488 0.4987 0.4797 0.032 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F31 C8 1.369(5) . ?
F32 C16 1.364(5) . ?
N29 C24 1.461(7) . ?
N29 C21 1.469(5) . ?
N29 C11 1.477(5) . ?
N30 C25 1.460(5) . ?
N30 C19 1.462(5) . ?
N30 C28 1.475(7) . ?
C1 C5 1.514(6) . ?
C1 C4 1.542(6) . ?
C1 C2 1.581(5) . ?
C1 H1 1.0000 . ?
C2 C11 1.499(6) . ?
C2 C3 1.571(6) . ?
C2 H2 1.0000 . ?
C3 C13 1.499(6) . ?
C3 C4 1.576(5) . ?
C3 H3 1.0000 . ?
C4 C19 1.548(6) . ?
C4 H4 1.0000 . ?
C5 C10 1.375(6) . ?
C5 C6 1.426(6) . ?
C6 C7 1.378(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(8) . ?
C9 C10 1.410(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.548(7) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.372(7) . ?
C13 C14 1.416(6) . ?
C14 C15 1.372(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(7) . ?
C17 C18 1.401(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.521(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.503(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.502(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.530(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.546(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.566(7) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.537(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
C24 N29 C21 104.4(3) . . ?
C24 N29 C11 117.7(4) . . ?
C21 N29 C11 116.1(4) . . ?
C25 N30 C19 114.7(3) . . ?
C25 N30 C28 104.4(3) . . ?
C19 N30 C28 117.0(4) . . ?
C5 C1 C4 116.8(4) . . ?
C5 C1 C2 121.4(4) . . ?
C4 C1 C2 89.8(3) . . ?
C5 C1 H1 109.1 . . ?
C4 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C11 C2 C3 116.8(4) . . ?
C11 C2 C1 120.4(3) . . ?
C3 C2 C1 90.0(3) . . ?
C11 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C13 C3 C2 116.1(4) . . ?
C13 C3 C4 122.3(3) . . ?
C2 C3 C4 88.9(3) . . ?
C13 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C1 C4 C19 117.2(4) . . ?
C1 C4 C3 91.2(3) . . ?
C19 C4 C3 119.8(3) . . ?
C1 C4 H4 109.1 . . ?
C19 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C10 C5 C6 117.7(4) . . ?
C10 C5 C1 120.4(4) . . ?
C6 C5 C1 121.7(4) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 123.0(5) . . ?
C9 C8 F31 118.1(5) . . ?
C7 C8 F31 118.9(5) . . ?
C8 C9 C10 117.9(5) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 H9 121.0 . . ?
C5 C10 C9 121.6(5) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N29 C11 C2 109.7(4) . . ?
N29 C11 C12 114.2(4) . . ?
C2 C11 C12 109.9(4) . . ?
N29 C11 H11 107.6 . . ?
C2 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.5(5) . . ?
C18 C13 C3 122.8(4) . . ?
C14 C13 C3 119.6(5) . . ?
C15 C14 C13 121.9(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 118.1(5) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
F32 C16 C17 118.1(5) . . ?
F32 C16 C15 119.4(5) . . ?
C17 C16 C15 122.5(5) . . ?
C16 C17 C18 117.5(5) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C13 C18 C17 122.4(4) . . ?
C13 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
N30 C19 C20 116.5(4) . . ?
N30 C19 C4 108.8(3) . . ?
C20 C19 C4 109.9(4) . . ?
N30 C19 H19 107.1 . . ?
C20 C19 H19 107.1 . . ?
C4 C19 H19 107.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N29 C21 C22 102.8(4) . . ?
N29 C21 H21A 111.2 . . ?
C22 C21 H21A 111.2 . . ?
N29 C21 H21B 111.2 . . ?
C22 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C23 C22 C21 105.1(4) . . ?
C23 C22 H22A 110.7 . . ?
C21 C22 H22A 110.7 . . ?
C23 C22 H22B 110.7 . . ?
C21 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
C22 C23 C24 105.8(4) . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?
N29 C24 C23 103.1(4) . . ?
N29 C24 H24A 111.2 . . ?
C23 C24 H24A 111.2 . . ?
N29 C24 H24B 111.2 . . ?
C23 C24 H24B 111.2 . . ?
H24A C24 H24B 109.1 . . ?
N30 C25 C26 102.3(4) . . ?
N30 C25 H25A 111.3 . . ?
C26 C25 H25A 111.3 . . ?
N30 C25 H25B 111.3 . . ?
C26 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
C25 C26 C27 103.0(4) . . ?
C25 C26 H26A 111.2 . . ?
C27 C26 H26A 111.2 . . ?
C25 C26 H26B 111.2 . . ?
C27 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
C28 C27 C26 104.8(4) . . ?
C28 C27 H27A 110.8 . . ?
C26 C27 H27A 110.8 . . ?
C28 C27 H27B 110.8 . . ?
C26 C27 H27B 110.8 . . ?
H27A C27 H27B 108.9 . . ?
N30 C28 C27 103.9(5) . . ?
N30 C28 H28A 111.0 . . ?
C27 C28 H28A 111.0 . . ?
N30 C28 H28B 111.0 . . ?
C27 C28 H28B 111.0 . . ?
H28A C28 H28B 109.0 . . ?

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
C5 C1 C2 C11 0.5(7) . . . . ?
C4 C1 C2 C11 -121.3(4) . . . . ?
C5 C1 C2 C3 122.0(4) . . . . ?
C4 C1 C2 C3 0.2(5) . . . . ?
C11 C2 C3 C13 -109.8(5) . . . . ?
C1 C2 C3 C13 125.6(3) . . . . ?
C11 C2 C3 C4 124.3(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C5 C1 C4 C19 109.4(5) . . . . ?
C2 C1 C4 C19 -125.0(3) . . . . ?
C5 C1 C4 C3 -125.8(3) . . . . ?
C2 C1 C4 C3 -0.2(5) . . . . ?
C13 C3 C4 C1 -120.3(4) . . . . ?
C2 C3 C4 C1 0.2(5) . . . . ?
C13 C3 C4 C19 2.3(7) . . . . ?
C2 C3 C4 C19 122.9(4) . . . . ?
C4 C1 C5 C10 -129.9(4) . . . . ?
C2 C1 C5 C10 122.4(5) . . . . ?
C4 C1 C5 C6 44.7(5) . . . . ?
C2 C1 C5 C6 -63.0(6) . . . . ?
C10 C5 C6 C7 0.2(6) . . . . ?
C1 C5 C6 C7 -174.4(4) . . . . ?
C5 C6 C7 C8 0.8(6) . . . . ?
C6 C7 C8 C9 -1.6(8) . . . . ?
C6 C7 C8 F31 178.0(4) . . . . ?
C7 C8 C9 C10 1.2(7) . . . . ?
F31 C8 C9 C10 -178.3(4) . . . . ?
C6 C5 C10 C9 -0.6(7) . . . . ?
C1 C5 C10 C9 174.2(4) . . . . ?
C8 C9 C10 C5 -0.1(7) . . . . ?
C24 N29 C11 C2 66.6(5) . . . . ?
C21 N29 C11 C2 -168.6(4) . . . . ?
C24 N29 C11 C12 -57.2(5) . . . . ?
C21 N29 C11 C12 67.6(6) . . . . ?
C3 C2 C11 N29 51.3(5) . . . . ?
C1 C2 C11 N29 158.6(4) . . . . ?
C3 C2 C11 C12 177.7(3) . . . . ?
C1 C2 C11 C12 -75.0(5) . . . . ?
C2 C3 C13 C18 -46.1(5) . . . . ?
C4 C3 C13 C18 60.5(6) . . . . ?
C2 C3 C13 C14 130.8(4) . . . . ?
C4 C3 C13 C14 -122.6(5) . . . . ?
C18 C13 C14 C15 2.2(7) . . . . ?
C3 C13 C14 C15 -174.9(4) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
C14 C15 C16 F32 179.2(4) . . . . ?
C14 C15 C16 C17 -0.6(7) . . . . ?
F32 C16 C17 C18 -178.9(4) . . . . ?
C15 C16 C17 C18 0.9(7) . . . . ?
C14 C13 C18 C17 -1.9(6) . . . . ?
C3 C13 C18 C17 175.1(4) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C25 N30 C19 C20 -65.9(6) . . . . ?
C28 N30 C19 C20 56.9(5) . . . . ?
C25 N30 C19 C4 169.3(4) . . . . ?
C28 N30 C19 C4 -67.9(5) . . . . ?
C1 C4 C19 N30 -50.6(5) . . . . ?
C3 C4 C19 N30 -159.4(4) . . . . ?
C1 C4 C19 C20 -179.3(4) . . . . ?
C3 C4 C19 C20 71.9(6) . . . . ?
C24 N29 C21 C22 -43.8(5) . . . . ?
C11 N29 C21 C22 -175.2(4) . . . . ?
N29 C21 C22 C23 30.1(5) . . . . ?
C21 C22 C23 C24 -6.2(5) . . . . ?
C21 N29 C24 C23 39.5(5) . . . . ?
C11 N29 C24 C23 169.9(4) . . . . ?
C22 C23 C24 N29 -20.0(5) . . . . ?
C19 N30 C25 C26 176.7(4) . . . . ?
C28 N30 C25 C26 47.3(5) . . . . ?
N30 C25 C26 C27 -34.0(5) . . . . ?
C25 C26 C27 C28 9.3(5) . . . . ?
C25 N30 C28 C27 -41.3(5) . . . . ?
C19 N30 C28 C27 -169.2(4) . . . . ?
C26 C27 C28 N30 18.3(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_DIOL-DIMER-3
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0hp
_database_code_depnum_ccdc_archive 'CCDC 2370802'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H22 F2 O2'
_chemical_formula_moiety         'C20 H22 F2 O2'
_chemical_formula_weight         332.39
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
_space_group_IT_number           13
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.5432
_cell_length_b                   10.8346
_cell_length_c                   20.4290
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.7120
_cell_angle_gamma                90.0000
_cell_volume                     3400.6556
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4531
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408.00
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.961

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

_diffrn_ambient_temperature      123
_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            36895
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         4.080
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6221
_reflns_number_gt                1626
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.1892
_refine_ls_R_factor_gt           0.0991
_refine_ls_wR_factor_ref         0.4346
_refine_ls_wR_factor_gt          0.3753
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6221
_refine_ls_number_parameters     442
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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          0.112
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(6)

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)
;
F F 0.0727 0.0534
;
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_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
F1 F 0.43061(18) 0.8575(3) -0.51409(13) 0.0613(11) Uani 1 1 d . . . . .
F2 F 0.07024(18) 0.8924(3) 0.01455(13) 0.0627(11) Uani 1 1 d . . . . .
F3 F 0.9306(2) 0.6072(3) -0.01375(16) 0.0737(12) Uani 1 1 d . . . . .
F4 F 0.5699(2) 0.6423(3) 0.51410(16) 0.0752(12) Uani 1 1 d . . . . .
O1 O 0.4096(2) 1.0738(3) -0.25650(15) 0.0517(11) Uani 1 1 d . . . . .
H1 H 0.3831 1.0681 -0.2954 0.062 Uiso 1 1 calc R U . . .
O2 O 0.0903(3) 0.6763(4) -0.2439(3) 0.1118(19) Uani 1 1 d . . . . .
H2A H 0.1039 0.6907 -0.2032 0.134 Uiso 1 1 calc R U . . .
O3 O 0.9088(2) 0.8237(4) 0.24346(17) 0.0617(12) Uani 1 1 d . . . . .
H3A H 0.8867 0.8144 0.2037 0.074 Uiso 1 1 calc R U . . .
O4 O 0.5911(3) 0.4260(5) 0.2565(3) 0.146(2) Uani 1 1 d . . . . .
H4 H 0.6105 0.4366 0.2967 0.175 Uiso 1 1 calc R U . . .
C1 C 0.3856(3) 0.8725(5) -0.4628(2) 0.0427(15) Uani 1 1 d . . . . .
C2 C 0.3993(3) 0.7880(5) -0.4116(2) 0.0446(15) Uani 1 1 d . . . . .
H2 H 0.4396 0.7223 -0.4122 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3524(3) 0.8016(5) -0.3594(2) 0.0431(14) Uani 1 1 d . . . . .
H3 H 0.3603 0.7436 -0.3242 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2937(3) 0.8989(5) -0.3575(2) 0.0395(14) Uani 1 1 d . . . . .
C5 C 0.2826(3) 0.9804(5) -0.4104(2) 0.0421(15) Uani 1 1 d . . . . .
H5 H 0.2425 1.0467 -0.4104 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3281(3) 0.9681(5) -0.4631(2) 0.0470(16) Uani 1 1 d . . . . .
H6 H 0.3196 1.0250 -0.4988 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2427(3) 0.9149(5) -0.3008(2) 0.0365(14) Uani 1 1 d . . . . .
H7 H 0.1927 0.9721 -0.3146 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2907(3) 0.9540(5) -0.2305(2) 0.0326(13) Uani 1 1 d . . . . .
H8 H 0.2622 1.0287 -0.2146 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2575(3) 0.8353(5) -0.1992(2) 0.0372(14) Uani 1 1 d . . . . .
H9 H 0.3075 0.7782 -0.1855 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2091(3) 0.7965(5) -0.2694(2) 0.0408(14) Uani 1 1 d . . . . .
H10 H 0.2374 0.7218 -0.2854 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3891(3) 0.9696(5) -0.2189(2) 0.0369(14) Uani 1 1 d . . . . .
H11 H 0.4171 0.8940 -0.2343 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4225(3) 0.9913(5) -0.1470(2) 0.0475(15) Uani 1 1 d . . . . .
H12A H 0.4859 1.0012 -0.1409 0.057 Uiso 1 1 calc R U . . .
H12B H 0.4075 0.9207 -0.1210 0.057 Uiso 1 1 calc R U . . .
H12C H 0.3959 1.0663 -0.1322 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2064(3) 0.8520(5) -0.1424(2) 0.0415(15) Uani 1 1 d . . . . .
C14 C 0.2185(3) 0.7685(5) -0.0894(2) 0.0419(15) Uani 1 1 d . . . . .
H14 H 0.2587 0.7025 -0.0894 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1718(3) 0.7819(5) -0.0368(2) 0.0462(15) Uani 1 1 d . . . . .
H15 H 0.1794 0.7246 -0.0012 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1153(3) 0.8777(5) -0.0369(3) 0.0433(15) Uani 1 1 d . . . . .
C17 C 0.1008(3) 0.9628(5) -0.0884(3) 0.0509(16) Uani 1 1 d . . . . .
H17 H 0.0606 1.0287 -0.0880 0.061 Uiso 1 1 calc R U . . .
C18 C 0.1478(3) 0.9472(6) -0.1404(2) 0.0513(16) Uani 1 1 d . . . . .
H18 H 0.1392 1.0042 -0.1762 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1114(4) 0.7811(5) -0.2810(3) 0.0534(16) Uani 1 1 d . . . . .
H19 H 0.0833 0.8566 -0.2656 0.064 Uiso 1 1 calc R U . . .
C20 C 0.0777(4) 0.7588(6) -0.3528(3) 0.088(2) Uani 1 1 d . . . . .
H20A H 0.0141 0.7520 -0.3590 0.106 Uiso 1 1 calc R U . . .
H20B H 0.1025 0.6821 -0.3672 0.106 Uiso 1 1 calc R U . . .
H20C H 0.0944 0.8278 -0.3793 0.106 Uiso 1 1 calc R U . . .
C21 C 0.8863(4) 0.6191(6) 0.0375(3) 0.0555(18) Uani 1 1 d . . . . .
C22 C 0.8970(4) 0.5378(5) 0.0879(3) 0.0515(16) Uani 1 1 d . . . . .
H22 H 0.9364 0.4710 0.0872 0.062 Uiso 1 1 calc R U . . .
C23 C 0.8516(3) 0.5500(5) 0.1403(2) 0.0470(15) Uani 1 1 d . . . . .
H23 H 0.8600 0.4915 0.1753 0.056 Uiso 1 1 calc R U . . .
C24 C 0.7928(3) 0.6486(5) 0.1426(3) 0.0437(15) Uani 1 1 d . . . . .
C25 C 0.7828(3) 0.7301(5) 0.0906(3) 0.0475(16) Uani 1 1 d . . . . .
H25 H 0.7433 0.7970 0.0910 0.057 Uiso 1 1 calc R U . . .
C26 C 0.8284(3) 0.7188(5) 0.0372(3) 0.0509(16) Uani 1 1 d . . . . .
H26 H 0.8205 0.7764 0.0018 0.061 Uiso 1 1 calc R U . . .
C27 C 0.7435(3) 0.6647(5) 0.1990(2) 0.0422(15) Uani 1 1 d . . . . .
H27 H 0.6935 0.7217 0.1852 0.051 Uiso 1 1 calc R U . . .
C28 C 0.7096(4) 0.5475(5) 0.2302(2) 0.0493(15) Uani 1 1 d . . . . .
H28 H 0.7379 0.4725 0.2145 0.059 Uiso 1 1 calc R U . . .
C29 C 0.7573(3) 0.5858(5) 0.3007(2) 0.0426(15) Uani 1 1 d . . . . .
H29 H 0.8075 0.5289 0.3143 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7901(3) 0.7040(5) 0.2694(2) 0.0389(14) Uani 1 1 d . . . . .
H30 H 0.7615 0.7788 0.2850 0.047 Uiso 1 1 calc R U . . .
C31 C 0.6115(4) 0.5313(6) 0.2195(3) 0.069(2) Uani 1 1 d . . . . .
H31 H 0.5836 0.6064 0.2354 0.083 Uiso 1 1 calc R U . . .
C32 C 0.7074(3) 0.6020(5) 0.3576(3) 0.0444(15) Uani 1 1 d . . . . .
C33 C 0.6487(4) 0.6988(5) 0.3610(3) 0.0580(17) Uani 1 1 d . . . . .
H33 H 0.6400 0.7571 0.3259 0.070 Uiso 1 1 calc R U . . .
C34 C 0.6032(4) 0.7126(5) 0.4131(3) 0.0621(18) Uani 1 1 d . . . . .
H34 H 0.5638 0.7793 0.4139 0.075 Uiso 1 1 calc R U . . .
C35 C 0.6152(4) 0.6301(6) 0.4634(3) 0.0558(18) Uani 1 1 d . . . . .
C36 C 0.6719(4) 0.5309(5) 0.4631(3) 0.0515(16) Uani 1 1 d . . . . .
H36 H 0.6789 0.4726 0.4982 0.062 Uiso 1 1 calc R U . . .
C37 C 0.7181(3) 0.5191(5) 0.4101(2) 0.0458(16) Uani 1 1 d . . . . .
H37 H 0.7579 0.4526 0.4099 0.055 Uiso 1 1 calc R U . . .
C38 C 0.8884(3) 0.7193(5) 0.2812(2) 0.0404(14) Uani 1 1 d . . . . .
H38 H 0.9162 0.6437 0.2655 0.048 Uiso 1 1 calc R U . . .
C39 C 0.9230(3) 0.7411(5) 0.3532(2) 0.0554(17) Uani 1 1 d . . . . .
H39A H 0.9863 0.7528 0.3585 0.066 Uiso 1 1 calc R U . . .
H39B H 0.9096 0.6697 0.3793 0.066 Uiso 1 1 calc R U . . .
H39C H 0.8958 0.8151 0.3686 0.066 Uiso 1 1 calc R U . . .
C40 C 0.5771(4) 0.5102(6) 0.1469(3) 0.109(3) Uani 1 1 d . . . . .
H40A H 0.5138 0.5001 0.1412 0.131 Uiso 1 1 calc R U . . .
H40B H 0.6036 0.4355 0.1316 0.131 Uiso 1 1 calc R U . . .
H40C H 0.5917 0.5812 0.1210 0.131 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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
F1 C1 1.355(5) . ?
F2 C16 1.358(5) . ?
F3 C21 1.344(5) . ?
F4 C35 1.345(5) . ?
O1 C11 1.428(5) . ?
O1 H1 0.8400 . ?
O2 C19 1.431(6) . ?
O2 H2A 0.8400 . ?
O3 C38 1.432(5) . ?
O3 H3A 0.8400 . ?
O4 C31 1.430(6) . ?
O4 H4 0.8400 . ?
C1 C6 1.368(7) . ?
C1 C2 1.381(6) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 C7 1.510(6) . ?
C5 C6 1.380(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.559(6) . ?
C7 C8 1.572(6) . ?
C7 H7 1.0000 . ?
C8 C11 1.522(6) . ?
C8 C9 1.559(6) . ?
C8 H8 1.0000 . ?
C9 C13 1.513(6) . ?
C9 C10 1.573(6) . ?
C9 H9 1.0000 . ?
C10 C19 1.511(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.500(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.381(7) . ?
C13 C14 1.401(6) . ?
C14 C15 1.392(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(6) . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.501(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.346(7) . ?
C21 C26 1.406(7) . ?
C22 C23 1.374(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.413(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(6) . ?
C24 C27 1.487(6) . ?
C25 C26 1.392(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.549(7) . ?
C27 C30 1.567(6) . ?
C27 H27 1.0000 . ?
C28 C31 1.517(7) . ?
C28 C29 1.573(6) . ?
C28 H28 1.0000 . ?
C29 C32 1.501(6) . ?
C29 C30 1.553(6) . ?
C29 H29 1.0000 . ?
C30 C38 1.519(6) . ?
C30 H30 1.0000 . ?
C31 C40 1.514(7) . ?
C31 H31 1.0000 . ?
C32 C37 1.390(6) . ?
C32 C33 1.399(7) . ?
C33 C34 1.373(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.352(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(7) . ?
C36 C37 1.392(6) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.507(6) . ?
C38 H38 1.0000 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
C11 O1 H1 109.5 . . ?
C19 O2 H2A 109.5 . . ?
C38 O3 H3A 109.5 . . ?
C31 O4 H4 109.5 . . ?
F1 C1 C6 120.1(5) . . ?
F1 C1 C2 117.9(5) . . ?
C6 C1 C2 122.1(5) . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.6(5) . . ?
C5 C4 C7 120.5(5) . . ?
C3 C4 C7 121.9(5) . . ?
C6 C5 C4 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 C10 117.9(4) . . ?
C4 C7 C8 120.0(4) . . ?
C10 C7 C8 89.3(3) . . ?
C4 C7 H7 109.3 . . ?
C10 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C11 C8 C9 114.5(4) . . ?
C11 C8 C7 120.0(4) . . ?
C9 C8 C7 90.7(3) . . ?
C11 C8 H8 110.1 . . ?
C9 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
C13 C9 C8 117.5(4) . . ?
C13 C9 C10 119.8(4) . . ?
C8 C9 C10 89.3(3) . . ?
C13 C9 H9 109.6 . . ?
C8 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C19 C10 C7 114.7(4) . . ?
C19 C10 C9 120.2(4) . . ?
C7 C10 C9 90.7(4) . . ?
C19 C10 H10 109.9 . . ?
C7 C10 H10 109.9 . . ?
C9 C10 H10 109.9 . . ?
O1 C11 C12 109.3(4) . . ?
O1 C11 C8 107.8(4) . . ?
C12 C11 C8 111.1(4) . . ?
O1 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
C8 C11 H11 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 118.1(5) . . ?
C18 C13 C9 122.4(5) . . ?
C14 C13 C9 119.4(5) . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F2 C16 C15 119.8(5) . . ?
F2 C16 C17 117.7(5) . . ?
C15 C16 C17 122.5(5) . . ?
C18 C17 C16 117.1(5) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C13 C18 C17 122.6(5) . . ?
C13 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
O2 C19 C20 108.4(5) . . ?
O2 C19 C10 108.1(5) . . ?
C20 C19 C10 111.4(5) . . ?
O2 C19 H19 109.6 . . ?
C20 C19 H19 109.6 . . ?
C10 C19 H19 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F3 C21 C22 121.0(6) . . ?
F3 C21 C26 118.2(6) . . ?
C22 C21 C26 120.7(5) . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 120.7(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 117.3(5) . . ?
C25 C24 C27 120.9(5) . . ?
C23 C24 C27 121.8(5) . . ?
C24 C25 C26 122.6(5) . . ?
C24 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 C21 117.8(5) . . ?
C25 C26 H26 121.1 . . ?
C21 C26 H26 121.1 . . ?
C24 C27 C28 118.1(4) . . ?
C24 C27 C30 121.5(4) . . ?
C28 C27 C30 89.1(3) . . ?
C24 C27 H27 108.9 . . ?
C28 C27 H27 108.9 . . ?
C30 C27 H27 108.8 . . ?
C31 C28 C27 115.7(5) . . ?
C31 C28 C29 119.1(5) . . ?
C27 C28 C29 91.1(4) . . ?
C31 C28 H28 109.9 . . ?
C27 C28 H28 109.9 . . ?
C29 C28 H28 109.9 . . ?
C32 C29 C30 117.6(4) . . ?
C32 C29 C28 120.9(4) . . ?
C30 C29 C28 88.7(3) . . ?
C32 C29 H29 109.3 . . ?
C30 C29 H29 109.3 . . ?
C28 C29 H29 109.3 . . ?
C38 C30 C29 114.2(4) . . ?
C38 C30 C27 119.3(4) . . ?
C29 C30 C27 91.1(4) . . ?
C38 C30 H30 110.3 . . ?
C29 C30 H30 110.3 . . ?
C27 C30 H30 110.3 . . ?
O4 C31 C40 108.9(6) . . ?
O4 C31 C28 108.3(5) . . ?
C40 C31 C28 110.9(5) . . ?
O4 C31 H31 109.6 . . ?
C40 C31 H31 109.6 . . ?
C28 C31 H31 109.6 . . ?
C37 C32 C33 116.6(5) . . ?
C37 C32 C29 120.5(5) . . ?
C33 C32 C29 122.9(5) . . ?
C34 C33 C32 122.4(5) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C35 C34 C33 119.3(6) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.3 . . ?
F4 C35 C34 119.5(6) . . ?
F4 C35 C36 119.0(6) . . ?
C34 C35 C36 121.5(6) . . ?
C35 C36 C37 118.4(5) . . ?
C35 C36 H36 120.8 . . ?
C37 C36 H36 120.8 . . ?
C32 C37 C36 121.7(5) . . ?
C32 C37 H37 119.1 . . ?
C36 C37 H37 119.2 . . ?
O3 C38 C39 109.0(4) . . ?
O3 C38 C30 107.5(4) . . ?
C39 C38 C30 112.0(4) . . ?
O3 C38 H38 109.4 . . ?
C39 C38 H38 109.4 . . ?
C30 C38 H38 109.4 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C31 C40 H40A 109.5 . . ?
C31 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C31 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
F1 C1 C2 C3 -179.0(4) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
C2 C3 C4 C7 -179.7(4) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C7 C4 C5 C6 -179.8(4) . . . . ?
F1 C1 C6 C5 179.4(4) . . . . ?
C2 C1 C6 C5 0.2(8) . . . . ?
C4 C5 C6 C1 0.1(8) . . . . ?
C5 C4 C7 C10 141.7(5) . . . . ?
C3 C4 C7 C10 -37.4(6) . . . . ?
C5 C4 C7 C8 -111.4(5) . . . . ?
C3 C4 C7 C8 69.5(6) . . . . ?
C4 C7 C8 C11 -3.0(7) . . . . ?
C10 C7 C8 C11 119.3(4) . . . . ?
C4 C7 C8 C9 -122.0(4) . . . . ?
C10 C7 C8 C9 0.3(4) . . . . ?
C11 C8 C9 C13 112.4(5) . . . . ?
C7 C8 C9 C13 -123.9(4) . . . . ?
C11 C8 C9 C10 -123.9(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C4 C7 C10 C19 -112.2(5) . . . . ?
C8 C7 C10 C19 123.7(4) . . . . ?
C4 C7 C10 C9 123.8(4) . . . . ?
C8 C7 C10 C9 -0.3(4) . . . . ?
C13 C9 C10 C19 2.6(7) . . . . ?
C8 C9 C10 C19 -119.1(5) . . . . ?
C13 C9 C10 C7 121.9(4) . . . . ?
C8 C9 C10 C7 0.3(4) . . . . ?
C9 C8 C11 O1 173.6(4) . . . . ?
C7 C8 C11 O1 67.4(5) . . . . ?
C9 C8 C11 C12 -66.7(5) . . . . ?
C7 C8 C11 C12 -172.8(4) . . . . ?
C8 C9 C13 C18 37.9(7) . . . . ?
C10 C9 C13 C18 -68.5(6) . . . . ?
C8 C9 C13 C14 -142.0(5) . . . . ?
C10 C9 C13 C14 111.5(5) . . . . ?
C18 C13 C14 C15 0.4(8) . . . . ?
C9 C13 C14 C15 -179.7(4) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 F2 -179.1(4) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
F2 C16 C17 C18 179.5(4) . . . . ?
C15 C16 C17 C18 -0.7(8) . . . . ?
C14 C13 C18 C17 0.0(8) . . . . ?
C9 C13 C18 C17 -180.0(4) . . . . ?
C16 C17 C18 C13 0.2(8) . . . . ?
C7 C10 C19 O2 -174.1(4) . . . . ?
C9 C10 C19 O2 -67.7(6) . . . . ?
C7 C10 C19 C20 66.8(6) . . . . ?
C9 C10 C19 C20 173.2(5) . . . . ?
F3 C21 C22 C23 -179.9(4) . . . . ?
C26 C21 C22 C23 0.0(9) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C22 C23 C24 C25 0.3(7) . . . . ?
C22 C23 C24 C27 -179.4(4) . . . . ?
C23 C24 C25 C26 -0.3(8) . . . . ?
C27 C24 C25 C26 179.4(4) . . . . ?
C24 C25 C26 C21 0.1(8) . . . . ?
F3 C21 C26 C25 180.0(4) . . . . ?
C22 C21 C26 C25 0.0(8) . . . . ?
C25 C24 C27 C28 142.3(5) . . . . ?
C23 C24 C27 C28 -38.0(6) . . . . ?
C25 C24 C27 C30 -109.9(6) . . . . ?
C23 C24 C27 C30 69.8(6) . . . . ?
C24 C27 C28 C31 -111.7(6) . . . . ?
C30 C27 C28 C31 122.6(5) . . . . ?
C24 C27 C28 C29 125.0(4) . . . . ?
C30 C27 C28 C29 -0.7(5) . . . . ?
C31 C28 C29 C32 2.1(7) . . . . ?
C27 C28 C29 C32 122.5(4) . . . . ?
C31 C28 C29 C30 -119.7(5) . . . . ?
C27 C28 C29 C30 0.7(5) . . . . ?
C32 C29 C30 C38 111.6(5) . . . . ?
C28 C29 C30 C38 -123.7(4) . . . . ?
C32 C29 C30 C27 -125.3(4) . . . . ?
C28 C29 C30 C27 -0.7(5) . . . . ?
C24 C27 C30 C38 -3.3(7) . . . . ?
C28 C27 C30 C38 119.5(4) . . . . ?
C24 C27 C30 C29 -122.1(5) . . . . ?
C28 C27 C30 C29 0.7(5) . . . . ?
C27 C28 C31 O4 -174.6(5) . . . . ?
C29 C28 C31 O4 -67.6(7) . . . . ?
C27 C28 C31 C40 66.0(7) . . . . ?
C29 C28 C31 C40 173.0(5) . . . . ?
C30 C29 C32 C37 -142.9(5) . . . . ?
C28 C29 C32 C37 110.7(6) . . . . ?
C30 C29 C32 C33 37.3(7) . . . . ?
C28 C29 C32 C33 -69.2(7) . . . . ?
C37 C32 C33 C34 0.0(8) . . . . ?
C29 C32 C33 C34 179.8(5) . . . . ?
C32 C33 C34 C35 0.1(9) . . . . ?
C33 C34 C35 F4 -179.0(5) . . . . ?
C33 C34 C35 C36 -0.7(9) . . . . ?
F4 C35 C36 C37 179.7(4) . . . . ?
C34 C35 C36 C37 1.3(9) . . . . ?
C33 C32 C37 C36 0.7(8) . . . . ?
C29 C32 C37 C36 -179.1(4) . . . . ?
C35 C36 C37 C32 -1.3(8) . . . . ?
C29 C30 C38 O3 173.7(4) . . . . ?
C27 C30 C38 O3 67.6(6) . . . . ?
C29 C30 C38 C39 -66.6(6) . . . . ?
C27 C30 C38 C39 -172.7(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_MEDMEIMINIUM-ANTI-HT-DIMER-1
_audit_block_doi                 10.5517/ccdc.csd.cc2kl0kr
_database_code_depnum_ccdc_archive 'CCDC 2370804'
loop_
_audit_author_name
_audit_author_address
'Shinji Yamada'
;Ochanomizu University
Japan
;
_audit_update_record             
;
2024-07-14 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_moiety         'C20 H20 O2'
_chemical_formula_weight         292.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.64367(19)
_cell_length_b                   16.3794(4)
_cell_length_c                   11.2234(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.7517(13)
_cell_angle_gamma                90.0000
_cell_volume                     1596.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4012
_cell_measurement_theta_min      4.38
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624.00
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.970

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

_diffrn_ambient_temperature      123
_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            9890
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         5.071
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2807
_reflns_number_gt                2370
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0506
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1070
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2807
_refine_ls_number_parameters     202
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0633P)²+0.6392P] 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         0.28
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(5)

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)
;

#==============================================================================
# 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_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
O1 O 0.26262(14) 0.41367(8) 0.17227(12) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.72689(14) 0.54194(7) 0.16386(12) 0.0298(3) Uani 1 1 d . . . . .
C1 C 0.48951(17) 0.34796(10) 0.18744(15) 0.0199(4) Uani 1 1 d . . . . .
H1 H 0.5187 0.2949 0.2360 0.024 Uiso 1 1 calc R U . . .
C2 C 0.56314(17) 0.35498(10) 0.08804(15) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.5023 0.3946 0.0166 0.024 Uiso 1 1 calc R U . . .
C3 C 0.70072(18) 0.40118(10) 0.20107(16) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.7855 0.3623 0.2530 0.024 Uiso 1 1 calc R U . . .
C4 C 0.59794(18) 0.41710(10) 0.27205(16) 0.0203(4) Uani 1 1 d . . . . .
H4 H 0.5450 0.4709 0.2426 0.024 Uiso 1 1 calc R U . . .
C5 C 0.31741(18) 0.36051(10) 0.13074(16) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.21977(19) 0.30489(11) 0.01967(18) 0.0290(4) Uani 1 1 d . . . . .
H6A H 0.1109 0.3137 -0.0018 0.035 Uiso 1 1 calc R U . . .
H6B H 0.2473 0.2480 0.0466 0.035 Uiso 1 1 calc R U . . .
H6C H 0.2373 0.3166 -0.0583 0.035 Uiso 1 1 calc R U . . .
C7 C 0.59702(17) 0.28040(10) 0.02709(16) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.67185(18) 0.21268(11) 0.10337(17) 0.0245(4) Uani 1 1 d . . . . .
H8 H 0.7007 0.2129 0.1958 0.029 Uiso 1 1 calc R U . . .
C9 C 0.70456(19) 0.14510(11) 0.04587(18) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.7547 0.0992 0.0988 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6643(2) 0.14430(12) -0.08894(19) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.6865 0.0980 -0.1285 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5916(2) 0.21143(12) -0.16499(18) 0.0307(4) Uani 1 1 d . . . . .
H11 H 0.5649 0.2115 -0.2570 0.037 Uiso 1 1 calc R U . . .
C12 C 0.55745(19) 0.27888(11) -0.10746(16) 0.0258(4) Uani 1 1 d . . . . .
H12 H 0.5064 0.3245 -0.1608 0.031 Uiso 1 1 calc R U . . .
C13 C 0.76131(18) 0.47170(10) 0.15203(16) 0.0220(4) Uani 1 1 d . . . . .
C14 C 0.8611(2) 0.45114(12) 0.08470(19) 0.0304(4) Uani 1 1 d . . . . .
H14A H 0.8240 0.4007 0.0336 0.037 Uiso 1 1 calc R U . . .
H14B H 0.9675 0.4435 0.1513 0.037 Uiso 1 1 calc R U . . .
H14C H 0.8571 0.4958 0.0251 0.037 Uiso 1 1 calc R U . . .
C15 C 0.66555(19) 0.41195(10) 0.42043(16) 0.0208(4) Uani 1 1 d . . . . .
C16 C 0.5689(2) 0.40464(11) 0.48248(18) 0.0287(4) Uani 1 1 d . . . . .
H16 H 0.4606 0.4029 0.4304 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6281(2) 0.39983(12) 0.61968(19) 0.0349(5) Uani 1 1 d . . . . .
H17 H 0.5604 0.3950 0.6605 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7857(2) 0.40212(12) 0.69657(18) 0.0326(5) Uani 1 1 d . . . . .
H18 H 0.8265 0.3989 0.7902 0.039 Uiso 1 1 calc R U . . .
C19 C 0.8833(2) 0.40918(11) 0.63632(18) 0.0306(4) Uani 1 1 d . . . . .
H19 H 0.9915 0.4105 0.6888 0.037 Uiso 1 1 calc R U . . .
C20 C 0.8237(2) 0.41435(11) 0.49900(17) 0.0256(4) Uani 1 1 d . . . . .
H20 H 0.8918 0.4196 0.4586 0.031 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# 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 C5 1.212(2) . ?
O2 C13 1.220(2) . ?
C1 C5 1.511(2) . ?
C1 C4 1.554(2) . ?
C1 C2 1.565(2) . ?
C1 H1 1.0000 . ?
C2 C7 1.504(2) . ?
C2 C3 1.575(2) . ?
C2 H2 1.0000 . ?
C3 C13 1.503(2) . ?
C3 C4 1.540(2) . ?
C3 H3 1.0000 . ?
C4 C15 1.504(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.500(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.388(2) . ?
C7 C8 1.395(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.498(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.390(2) . ?
C15 C20 1.392(2) . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(2) . ?
C19 H19 0.9500 . ?
C20 H20 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
C5 C1 C4 118.85(14) . . ?
C5 C1 C2 116.43(13) . . ?
C4 C1 C2 89.36(12) . . ?
C5 C1 H1 110.2 . . ?
C4 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
C7 C2 C1 121.34(14) . . ?
C7 C2 C3 118.90(13) . . ?
C1 C2 C3 86.88(11) . . ?
C7 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C13 C3 C4 119.97(14) . . ?
C13 C3 C2 113.58(13) . . ?
C4 C3 C2 89.52(12) . . ?
C13 C3 H3 110.7 . . ?
C4 C3 H3 110.7 . . ?
C2 C3 H3 110.7 . . ?
C15 C4 C3 119.77(13) . . ?
C15 C4 C1 119.25(13) . . ?
C3 C4 C1 88.50(12) . . ?
C15 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C1 C4 H4 109.2 . . ?
O1 C5 C6 122.33(15) . . ?
O1 C5 C1 121.22(15) . . ?
C6 C5 C1 116.44(15) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.54(16) . . ?
C12 C7 C2 119.88(15) . . ?
C8 C7 C2 121.56(15) . . ?
C9 C8 C7 120.74(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.17(17) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.48(17) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.31(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.75(17) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O2 C13 C14 122.12(16) . . ?
O2 C13 C3 121.15(16) . . ?
C14 C13 C3 116.70(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.29(16) . . ?
C16 C15 C4 119.81(15) . . ?
C20 C15 C4 121.90(15) . . ?
C15 C16 C17 121.11(16) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.97(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.59(17) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.35(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 120.68(17) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?

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
C5 C1 C2 C7 -97.77(17) . . . . ?
C4 C1 C2 C7 140.00(14) . . . . ?
C5 C1 C2 C3 139.99(14) . . . . ?
C4 C1 C2 C3 17.76(11) . . . . ?
C7 C2 C3 C13 94.90(17) . . . . ?
C1 C2 C3 C13 -140.71(14) . . . . ?
C7 C2 C3 C4 -142.32(14) . . . . ?
C1 C2 C3 C4 -17.93(11) . . . . ?
C13 C3 C4 C15 -101.53(17) . . . . ?
C2 C3 C4 C15 141.29(14) . . . . ?
C13 C3 C4 C1 135.23(14) . . . . ?
C2 C3 C4 C1 18.04(11) . . . . ?
C5 C1 C4 C15 98.01(18) . . . . ?
C2 C1 C4 C15 -141.85(14) . . . . ?
C5 C1 C4 C3 -138.30(14) . . . . ?
C2 C1 C4 C3 -18.16(11) . . . . ?
C4 C1 C5 O1 -16.4(2) . . . . ?
C2 C1 C5 O1 -121.42(17) . . . . ?
C4 C1 C5 C6 162.57(14) . . . . ?
C2 C1 C5 C6 57.5(2) . . . . ?
C1 C2 C7 C12 134.56(15) . . . . ?
C3 C2 C7 C12 -120.17(16) . . . . ?
C1 C2 C7 C8 -47.3(2) . . . . ?
C3 C2 C7 C8 58.0(2) . . . . ?
C12 C7 C8 C9 -0.6(2) . . . . ?
C2 C7 C8 C9 -178.83(15) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
C2 C7 C12 C11 178.21(15) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C4 C3 C13 O2 -2.2(2) . . . . ?
C2 C3 C13 O2 101.77(18) . . . . ?
C4 C3 C13 C14 179.68(14) . . . . ?
C2 C3 C13 C14 -76.36(17) . . . . ?
C3 C4 C15 C16 -163.00(16) . . . . ?
C1 C4 C15 C16 -56.4(2) . . . . ?
C3 C4 C15 C20 17.1(2) . . . . ?
C1 C4 C15 C20 123.69(17) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?
C4 C15 C16 C17 -179.93(16) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C4 C15 C20 C19 -179.79(15) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
