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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_duro_auto
_database_code_depnum_ccdc_archive 'CCDC 2369867'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Ibaraki University
Japan
;
_audit_update_record             
;
2024-07-11 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT084_duro_auto           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.49 Report
RESPONSE: This is due to the poor crystal quality.
;
_vrf_PLAT934_duro_auto           
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..         15 Check
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT082_duro_auto           
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: This is due to the poor crystal quality.
;
# Added during the CSD deposition process: Thursday 11 July 2024 08:22 AM
# end Validation Reply Form

_audit_creation_date             2024-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
4-[2-(4-Cyano-2,3,5,6-tetrafluorophenyl)ethyn-1-yl]julolidine
_chemical_formula_moiety         'C21 H14 F4 N2'
_chemical_formula_sum            'C21 H14 F4 N2'
_chemical_formula_weight         370.34
_chemical_melting_point          470.6--472.9
_chemical_oxdiff_formula         C21H14F4N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7485(5)
_cell_length_b                   8.3818(7)
_cell_length_c                   15.2313(16)
_cell_angle_alpha                93.866(8)
_cell_angle_beta                 91.617(8)
_cell_angle_gamma                97.057(7)
_cell_volume                     852.50(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2985
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.0530
_cell_measurement_theta_min      3.2950
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 3 -1 0.1629
-7 -2 14 0.1165
-7 3 -14 0.1401
-5 -10 5 0.0859
-1 -11 -3 0.0577
-1 0 21 0.0075
0 -11 9 0.0429
0 11 -10 0.0661
0 0 -1 0.0466
0 11 4 0.0597
1 0 21 0.0121
1 2 -2 0.1115
5 -1 -3 0.1464

_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.057
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.4084 3.0681 -0.7370 -0.8842 0.2875 -0.3682
-6.9794 -1.7589 14.4206 -0.6875 -0.4992 -0.5274
-6.8093 2.7852 -14.4043 -0.4817 0.8346 -0.2673
-4.5066 -9.5025 4.6947 -0.0438 -0.2047 -0.9778
-1.0182 -11.2229 -3.0986 0.4131 0.0433 -0.9097
-0.5592 -0.4125 21.4547 -0.3092 -0.9510 0.0003
-0.3314 -10.8978 9.0902 0.2968 -0.5147 -0.8044
-0.0577 10.8206 -9.7035 -0.3175 0.5505 0.7721
0.0001 0.0001 -1.0001 0.0131 0.0447 -0.0031
0.3979 11.3180 3.5912 -0.4741 -0.0497 0.8791
0.8835 0.0321 21.2375 -0.2065 -0.9706 0.1239
0.9990 2.0017 -1.9977 0.0265 0.0871 0.2060
4.9988 -0.9950 -2.9950 0.4882 0.0055 0.2325

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.880
_diffrn_ambient_temperature      200
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  73.00   0.50    4.00    --  -13.20  46.00 150.00  216
  2  ω    -93.00 -64.00   0.50    4.00    --  -13.20  55.00 -90.00   58
  3  ω    -25.00  75.00   0.50    4.00    --  -13.20  55.00 -90.00  200
  4  ω   -103.00 -59.00   0.50    4.00    --  -13.20  55.00 -30.00   88
  5  ω     11.00  70.00   0.50    4.00    --  -13.20  55.00 -30.00  118
  6  ω    -97.00 -71.00   0.50    4.00    --  -13.20  18.00-180.00   52
  7  ω    -59.00  73.00   0.50    4.00    --  -13.20  18.00-180.00  264
  8  ω      6.00  31.00   0.50    4.00    --  -13.20  55.00  30.00   50
  9  ω     47.00  73.00   0.50    4.00    --  -13.20  55.00  30.00   52
 10  ω    -92.00 -67.00   0.50    4.00    --  -13.20  46.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0817540000
_diffrn_orient_matrix_UB_12      -0.0406191000
_diffrn_orient_matrix_UB_13      -0.0130636000
_diffrn_orient_matrix_UB_21      -0.0235858000
_diffrn_orient_matrix_UB_22      0.0106292000
_diffrn_orient_matrix_UB_23      -0.0447357000
_diffrn_orient_matrix_UB_31      0.0631793000
_diffrn_orient_matrix_UB_32      0.0744674000
_diffrn_orient_matrix_UB_33      0.0030916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2696
_reflns_number_total             3900
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.1578
_refine_ls_restrained_S_all      1.919
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4750
_refine_ls_wR_factor_ref         0.4860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00N(H00C,H00E), C00O(H00F,H00G), C00P(H00H,H00I), C00Q(H00J,
 H00K), C00R(H00L,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.2572(6) 0.6637(4) 0.6473(2) 0.0503(11) Uani 1 1 d . . . . .
F002 F 0.2490(6) 0.5176(5) 0.7984(2) 0.0533(11) Uani 1 1 d . . . . .
F003 F 0.2151(7) 0.1590(4) 0.4885(2) 0.0557(11) Uani 1 1 d . . . . .
F004 F 0.2033(6) 0.0142(4) 0.6397(3) 0.0571(12) Uani 1 1 d . . . . .
N005 N 0.2798(7) 0.8951(5) 0.1087(3) 0.0288(10) Uani 1 1 d . . . . .
C006 C 0.2723(7) 0.8153(6) 0.1846(3) 0.0249(11) Uani 1 1 d . . . . .
N007 N 0.2115(8) 0.1267(8) 0.8692(4) 0.0571(17) Uani 1 1 d . . . . .
C008 C 0.2393(7) 0.4165(6) 0.5637(3) 0.0257(11) Uani 1 1 d . . . . .
C009 C 0.2416(7) 0.5667(6) 0.2574(3) 0.0266(11) Uani 1 1 d . . . . .
H009 H 0.225659 0.452240 0.254370 0.032 Uiso 1 1 calc R U . . .
C00A C 0.2457(7) 0.6446(6) 0.1801(3) 0.0241(11) Uani 1 1 d . . . . .
C10 C 0.2547(7) 0.5679(6) 0.4188(3) 0.0283(12) Uani 1 1 d . . . . .
C00C C 0.2603(7) 0.6525(6) 0.3400(3) 0.0246(11) Uani 1 1 d . . . . .
C00D C 0.2887(7) 0.8200(6) 0.3428(3) 0.0266(11) Uani 1 1 d . . . . .
H00D H 0.305766 0.879014 0.398537 0.032 Uiso 1 1 calc R U . . .
C00E C 0.2169(8) 0.1747(6) 0.6432(4) 0.0331(13) Uani 1 1 d . . . . .
C00F C 0.2476(7) 0.4958(7) 0.4838(3) 0.0313(12) Uani 1 1 d . . . . .
C00G C 0.2266(7) 0.2637(7) 0.7225(3) 0.0299(12) Uani 1 1 d . . . . .
C00H C 0.2185(8) 0.1870(8) 0.8041(4) 0.0407(14) Uani 1 1 d . . . . .
C00I C 0.2931(7) 0.9036(6) 0.2682(3) 0.0245(11) Uani 1 1 d . . . . .
C00J C 0.2417(8) 0.4288(7) 0.7220(3) 0.0310(12) Uani 1 1 d . . . . .
C00K C 0.2235(8) 0.2493(7) 0.5648(3) 0.0319(12) Uani 1 1 d . . . . .
C00L C 0.2478(8) 0.5035(6) 0.6440(3) 0.0296(12) Uani 1 1 d . . . . .
C00M C 0.2865(9) 1.0695(7) 0.1121(4) 0.0377(13) Uani 1 1 d . . . . .
H00A H 0.149139 1.098916 0.115307 0.045 Uiso 1 1 calc R U . . .
H00B H 0.344750 1.110104 0.057652 0.045 Uiso 1 1 calc R U . . .
C00N C 0.2348(9) 0.8080(7) 0.0236(3) 0.0365(13) Uani 1 1 d . . . . .
H00C H 0.295597 0.872937 -0.022913 0.044 Uiso 1 1 calc R U . . .
H00E H 0.088315 0.791466 0.012163 0.044 Uiso 1 1 calc R U . . .
C00O C 0.4109(9) 1.1474(7) 0.1914(4) 0.0376(13) Uani 1 1 d . . . . .
H00F H 0.414040 1.265934 0.192974 0.045 Uiso 1 1 calc R U . . .
H00G H 0.549802 1.121539 0.187323 0.045 Uiso 1 1 calc R U . . .
C00P C 0.3124(9) 0.6478(7) 0.0196(3) 0.0374(14) Uani 1 1 d . . . . .
H00H H 0.459837 0.663887 0.027510 0.045 Uiso 1 1 calc R U . . .
H00I H 0.277440 0.590274 -0.038694 0.045 Uiso 1 1 calc R U . . .
C00Q C 0.2227(9) 0.5484(7) 0.0911(4) 0.0381(14) Uani 1 1 d . . . . .
H00J H 0.289764 0.450239 0.094171 0.046 Uiso 1 1 calc R U . . .
H00K H 0.079133 0.514397 0.076543 0.046 Uiso 1 1 calc R U . . .
C00R C 0.3207(9) 1.0850(6) 0.2745(4) 0.0357(13) Uani 1 1 d . . . . .
H00L H 0.409591 1.125883 0.326072 0.043 Uiso 1 1 calc R U . . .
H00M H 0.189880 1.124834 0.282994 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00L 1.334(6) . ?
F002 C00J 1.335(6) . ?
F003 C00K 1.339(6) . ?
F004 C00E 1.334(6) . ?
N005 C006 1.373(6) . ?
N005 C00M 1.455(7) . ?
N005 C00N 1.449(7) . ?
C006 C00A 1.417(7) . ?
C006 C00I 1.424(7) . ?
N007 C00H 1.142(7) . ?
C008 C00F 1.426(6) . ?
C008 C00K 1.393(8) . ?
C008 C00L 1.377(7) . ?
C009 H009 0.9500 . ?
C009 C00A 1.384(6) . ?
C009 C00C 1.401(7) . ?
C00A C00Q 1.524(7) . ?
C10 C00C 1.433(6) . ?
C10 C00F 1.193(7) . ?
C00C C00D 1.392(7) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.373(7) . ?
C00E C00G 1.372(8) . ?
C00E C00K 1.384(7) . ?
C00G C00H 1.437(7) . ?
C00G C00J 1.376(8) . ?
C00I C00R 1.505(7) . ?
C00J C00L 1.379(7) . ?
C00M H00A 0.9900 . ?
C00M H00B 0.9900 . ?
C00M C00O 1.514(8) . ?
C00N H00C 0.9900 . ?
C00N H00E 0.9900 . ?
C00N C00P 1.498(8) . ?
C00O H00F 0.9900 . ?
C00O H00G 0.9900 . ?
C00O C00R 1.518(8) . ?
C00P H00H 0.9900 . ?
C00P H00I 0.9900 . ?
C00P C00Q 1.510(8) . ?
C00Q H00J 0.9900 . ?
C00Q H00K 0.9900 . ?
C00R H00L 0.9900 . ?
C00R H00M 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
C006 N005 C00M 120.7(4) . . ?
C006 N005 C00N 120.8(4) . . ?
C00N N005 C00M 117.0(4) . . ?
N005 C006 C00A 120.1(4) . . ?
N005 C006 C00I 120.2(4) . . ?
C00A C006 C00I 119.6(4) . . ?
C00K C008 C00F 122.2(4) . . ?
C00L C008 C00F 120.8(5) . . ?
C00L C008 C00K 117.0(4) . . ?
C00A C009 H009 119.2 . . ?
C00A C009 C00C 121.6(4) . . ?
C00C C009 H009 119.2 . . ?
C006 C00A C00Q 120.3(4) . . ?
C009 C00A C006 119.2(4) . . ?
C009 C00A C00Q 120.6(4) . . ?
C00F C10 C00C 178.9(6) . . ?
C009 C00C C10 120.2(4) . . ?
C00D C00C C009 118.2(4) . . ?
C00D C00C C10 121.6(4) . . ?
C00C C00D H00D 118.7 . . ?
C00I C00D C00C 122.7(4) . . ?
C00I C00D H00D 118.7 . . ?
F004 C00E C00G 120.8(5) . . ?
F004 C00E C00K 118.3(5) . . ?
C00G C00E C00K 120.8(5) . . ?
C10 C00F C008 177.4(6) . . ?
C00E C00G C00H 121.1(5) . . ?
C00E C00G C00J 118.2(5) . . ?
C00J C00G C00H 120.6(5) . . ?
N007 C00H C00G 179.6(8) . . ?
C006 C00I C00R 120.5(4) . . ?
C00D C00I C006 118.7(4) . . ?
C00D C00I C00R 120.8(4) . . ?
F002 C00J C00G 119.2(5) . . ?
F002 C00J C00L 119.6(5) . . ?
C00G C00J C00L 121.1(5) . . ?
F003 C00K C008 119.4(5) . . ?
F003 C00K C00E 119.3(5) . . ?
C00E C00K C008 121.3(5) . . ?
F001 C00L C008 119.8(4) . . ?
F001 C00L C00J 118.6(5) . . ?
C008 C00L C00J 121.5(5) . . ?
N005 C00M H00A 109.5 . . ?
N005 C00M H00B 109.5 . . ?
N005 C00M C00O 110.6(4) . . ?
H00A C00M H00B 108.1 . . ?
C00O C00M H00A 109.5 . . ?
C00O C00M H00B 109.5 . . ?
N005 C00N H00C 109.3 . . ?
N005 C00N H00E 109.3 . . ?
N005 C00N C00P 111.5(4) . . ?
H00C C00N H00E 108.0 . . ?
C00P C00N H00C 109.3 . . ?
C00P C00N H00E 109.3 . . ?
C00M C00O H00F 109.8 . . ?
C00M C00O H00G 109.8 . . ?
C00M C00O C00R 109.3(5) . . ?
H00F C00O H00G 108.3 . . ?
C00R C00O H00F 109.8 . . ?
C00R C00O H00G 109.8 . . ?
C00N C00P H00H 109.7 . . ?
C00N C00P H00I 109.7 . . ?
C00N C00P C00Q 109.8(5) . . ?
H00H C00P H00I 108.2 . . ?
C00Q C00P H00H 109.7 . . ?
C00Q C00P H00I 109.7 . . ?
C00A C00Q H00J 109.5 . . ?
C00A C00Q H00K 109.5 . . ?
C00P C00Q C00A 110.9(5) . . ?
C00P C00Q H00J 109.5 . . ?
C00P C00Q H00K 109.5 . . ?
H00J C00Q H00K 108.0 . . ?
C00I C00R C00O 110.3(4) . . ?
C00I C00R H00L 109.6 . . ?
C00I C00R H00M 109.6 . . ?
C00O C00R H00L 109.6 . . ?
C00O C00R H00M 109.6 . . ?
H00L C00R H00M 108.1 . . ?

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
F002 C00J C00L F001 -1.2(8) . . . . ?
F002 C00J C00L C008 -179.6(5) . . . . ?
F004 C00E C00G C00H -1.3(8) . . . . ?
F004 C00E C00G C00J 179.6(5) . . . . ?
F004 C00E C00K F003 0.4(8) . . . . ?
F004 C00E C00K C008 -179.5(5) . . . . ?
N005 C006 C00A C009 179.0(4) . . . . ?
N005 C006 C00A C00Q -0.8(7) . . . . ?
N005 C006 C00I C00D -178.8(4) . . . . ?
N005 C006 C00I C00R 0.9(7) . . . . ?
N005 C00M C00O C00R -59.3(6) . . . . ?
N005 C00N C00P C00Q 58.3(6) . . . . ?
C006 N005 C00M C00O 36.6(7) . . . . ?
C006 N005 C00N C00P -37.5(7) . . . . ?
C006 C00A C00Q C00P 22.8(7) . . . . ?
C006 C00I C00R C00O -24.9(7) . . . . ?
C009 C00A C00Q C00P -156.9(5) . . . . ?
C009 C00C C00D C00I 1.9(7) . . . . ?
C00A C006 C00I C00D 0.6(7) . . . . ?
C00A C006 C00I C00R -179.7(4) . . . . ?
C00A C009 C00C C10 179.8(4) . . . . ?
C00A C009 C00C C00D -1.6(7) . . . . ?
C10 C00C C00D C00I -179.5(4) . . . . ?
C00C C009 C00A C006 0.9(7) . . . . ?
C00C C009 C00A C00Q -179.3(5) . . . . ?
C00C C00D C00I C006 -1.4(7) . . . . ?
C00C C00D C00I C00R 178.9(5) . . . . ?
C00D C00I C00R C00O 154.8(5) . . . . ?
C00E C00G C00J F002 179.2(5) . . . . ?
C00E C00G C00J C00L -0.2(8) . . . . ?
C00F C008 C00K F003 -0.3(8) . . . . ?
C00F C008 C00K C00E 179.6(5) . . . . ?
C00F C008 C00L F001 2.3(8) . . . . ?
C00F C008 C00L C00J -179.4(5) . . . . ?
C00G C00E C00K F003 179.5(5) . . . . ?
C00G C00E C00K C008 -0.3(8) . . . . ?
C00G C00J C00L F001 178.2(4) . . . . ?
C00G C00J C00L C008 -0.1(8) . . . . ?
C00H C00G C00J F002 0.0(7) . . . . ?
C00H C00G C00J C00L -179.4(5) . . . . ?
C00I C006 C00A C009 -0.3(7) . . . . ?
C00I C006 C00A C00Q 179.9(4) . . . . ?
C00K C008 C00L F001 -178.1(4) . . . . ?
C00K C008 C00L C00J 0.2(8) . . . . ?
C00K C00E C00G C00H 179.6(5) . . . . ?
C00K C00E C00G C00J 0.4(8) . . . . ?
C00L C008 C00K F003 -179.9(5) . . . . ?
C00L C008 C00K C00E 0.0(8) . . . . ?
C00M N005 C006 C00A 173.7(4) . . . . ?
C00M N005 C006 C00I -6.9(7) . . . . ?
C00M N005 C00N C00P 156.5(5) . . . . ?
C00M C00O C00R C00I 52.9(6) . . . . ?
C00N N005 C006 C00A 8.2(7) . . . . ?
C00N N005 C006 C00I -172.4(5) . . . . ?
C00N N005 C00M C00O -157.4(5) . . . . ?
C00N C00P C00Q C00A -50.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.732
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and CH2Cl2'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_jld-h_auto
_database_code_depnum_ccdc_archive 'CCDC 2401628'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Ibaraki University
Japan
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_audit_creation_date             2024-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            JLD-H
_chemical_name_systematic        4-[2-(4-Cyanophenyl)ethyn-1-yl]julolidine
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37
_chemical_melting_point          '162.9--163.5 ?C'
_chemical_oxdiff_formula         C21H18N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5475(8)
_cell_length_b                   8.1404(3)
_cell_length_c                   15.4286(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.086(6)
_cell_angle_gamma                90
_cell_volume                     1587.57(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.6630
_cell_measurement_theta_min      3.4470
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 2 -22 0.1712
2 -10 -11 0.1604
-7 -6 19 0.1615
-8 -2 22 0.1658
-3 9 13 0.1695
5 10 -9 0.1410
18 -2 -3 0.0622
-17 -1 -2 0.0535
16 2 3 0.0593
-7 8 -9 0.1262
-4 1 -18 0.1456
5 -2 17 0.1238
18 2 -3 0.0588
12 -2 10 0.0824

_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.114
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.8338 1.5003 -21.5360 0.8333 -0.2709 0.4819
2.2619 -10.0054 -10.5543 -0.1245 0.0406 0.9914
-7.4803 -5.7038 18.7899 -0.9451 0.3073 -0.1115
-7.8355 -1.5317 21.5278 -0.8345 0.2713 -0.4795
-3.1006 9.3163 12.6404 0.0168 -0.0055 -0.9998
4.6698 10.4055 -8.8869 0.8294 -0.2697 -0.4892
18.3421 -1.7012 -2.7087 0.4027 0.9038 0.1449
-17.0820 -1.4373 -1.7153 -0.3990 -0.8958 0.1960
16.4561 2.1984 2.7937 0.3909 0.8775 -0.2779
-7.0148 8.3217 -8.9572 0.4752 -0.8237 -0.3094
-4.3717 1.3393 -17.8271 0.4532 -0.7852 0.4220
4.9228 -2.4368 17.1187 -0.4724 0.8186 -0.3268
18.3444 1.9954 -3.1029 0.5849 0.8046 -0.1024
12.1854 -2.0071 10.2313 -0.1026 0.9779 -0.1823

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11183
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.875
_diffrn_ambient_temperature      173
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -46.00   0.50    1.53    --  -13.20  28.00 -90.00   54
  2  ω     40.00  76.00   0.50    1.53    --  -13.20  28.00 -90.00   72
  3  ω    -98.00  24.00   0.50    1.53    --  -13.20  28.00 120.00  244
  4  ω    -95.00  27.00   0.50    1.53    --  -13.20   9.00-180.00  244
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0222087000
_diffrn_orient_matrix_UB_12      0.0463519000
_diffrn_orient_matrix_UB_13      -0.0273845000
_diffrn_orient_matrix_UB_21      0.0514550000
_diffrn_orient_matrix_UB_22      -0.0236943000
_diffrn_orient_matrix_UB_23      0.0296465000
_diffrn_orient_matrix_UB_31      -0.0027544000
_diffrn_orient_matrix_UB_32      -0.0699087000
_diffrn_orient_matrix_UB_33      -0.0282499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2867
_reflns_number_total             3645
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.2273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C1(H1A,H1B), C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C11(H11), C17(H17), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 0.17004(8) 0.26370(12) 0.75314(7) 0.0260(2) Uani 1 1 d . . . . .
C4 C 0.25254(9) 0.27820(13) 0.72152(7) 0.0222(2) Uani 1 1 d . . . . .
C3 C 0.34582(9) 0.36249(14) 0.77553(8) 0.0248(3) Uani 1 1 d . . . . .
N23 N 0.93298(9) 0.38917(16) 0.37768(9) 0.0419(3) Uani 1 1 d . . . . .
C10 C 0.24670(9) 0.20628(14) 0.63657(8) 0.0257(3) Uani 1 1 d . . . . .
C16 C 0.64354(9) 0.36662(14) 0.54049(8) 0.0260(3) Uani 1 1 d . . . . .
C19 C 0.79278(9) 0.37871(14) 0.45521(8) 0.0267(3) Uani 1 1 d . . . . .
C14 C 0.50308(10) 0.33665(15) 0.62063(8) 0.0296(3) Uani 1 1 d . . . . .
C18 C 0.81493(9) 0.45028(15) 0.54203(9) 0.0301(3) Uani 1 1 d . . . . .
H18 H 0.881011 0.502930 0.572306 0.036 Uiso 1 1 calc R U . . .
C13 C 0.42672(9) 0.38204(15) 0.74204(8) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.487423 0.443798 0.777231 0.032 Uiso 1 1 calc R U . . .
C11 C 0.33106(9) 0.22297(15) 0.60735(8) 0.0275(3) Uani 1 1 d . . . . .
H11 H 0.327677 0.171426 0.551110 0.033 Uiso 1 1 calc R U . . .
C17 C 0.74065(10) 0.44461(15) 0.58408(9) 0.0299(3) Uani 1 1 d . . . . .
H17 H 0.755743 0.494202 0.643195 0.036 Uiso 1 1 calc R U . . .
C15 C 0.56770(10) 0.35438(15) 0.58477(9) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.42152(9) 0.31313(15) 0.65756(8) 0.0267(3) Uani 1 1 d . . . . .
C20 C 0.69530(9) 0.30296(16) 0.41015(9) 0.0303(3) Uani 1 1 d . . . . .
H20 H 0.679656 0.255721 0.350384 0.036 Uiso 1 1 calc R U . . .
C21 C 0.62191(9) 0.29713(16) 0.45286(9) 0.0312(3) Uani 1 1 d . . . . .
H21 H 0.555679 0.245106 0.422275 0.037 Uiso 1 1 calc R U . . .
C2 C 0.35106(10) 0.43191(17) 0.86734(8) 0.0316(3) Uani 1 1 d . . . . .
H2A H 0.404970 0.519987 0.886986 0.038 Uiso 1 1 calc R U . . .
H2B H 0.371406 0.344696 0.915265 0.038 Uiso 1 1 calc R U . . .
C22 C 0.87049(10) 0.38569(15) 0.41167(9) 0.0309(3) Uani 1 1 d . . . . .
C6 C 0.16105(10) 0.36599(16) 0.82756(9) 0.0320(3) Uani 1 1 d . . . . .
H6A H 0.168307 0.295682 0.881866 0.038 Uiso 1 1 calc R U . . .
H6B H 0.089763 0.416281 0.806469 0.038 Uiso 1 1 calc R U . . .
C1 C 0.24332(10) 0.50069(16) 0.85720(9) 0.0329(3) Uani 1 1 d . . . . .
H1A H 0.245893 0.547623 0.917177 0.040 Uiso 1 1 calc R U . . .
H1B H 0.223983 0.589641 0.810305 0.040 Uiso 1 1 calc R U . . .
C9 C 0.14827(10) 0.11524(18) 0.57870(9) 0.0353(3) Uani 1 1 d . . . . .
H9A H 0.167373 0.025248 0.544511 0.042 Uiso 1 1 calc R U . . .
H9B H 0.099959 0.191063 0.532610 0.042 Uiso 1 1 calc R U . . .
C7 C 0.07293(10) 0.17915(18) 0.69888(9) 0.0365(3) Uani 1 1 d . . . . .
H7A H 0.022118 0.259395 0.658500 0.044 Uiso 1 1 calc R U . . .
H7B H 0.040801 0.130566 0.741330 0.044 Uiso 1 1 calc R U . . .
C8 C 0.09290(12) 0.04504(18) 0.63941(10) 0.0421(4) Uani 1 1 d . . . . .
H8A H 0.137172 -0.042047 0.679665 0.051 Uiso 1 1 calc R U . . .
H8B H 0.024818 -0.004729 0.600100 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 C4 1.3761(14) . ?
N5 C6 1.4584(15) . ?
N5 C7 1.4536(16) . ?
C4 C3 1.4158(16) . ?
C4 C10 1.4114(16) . ?
C3 C13 1.3788(16) . ?
C3 C2 1.5028(16) . ?
N23 C22 1.1455(16) . ?
C10 C11 1.3779(16) . ?
C10 C9 1.5061(17) . ?
C16 C17 1.3963(17) . ?
C16 C15 1.4273(16) . ?
C16 C21 1.3961(17) . ?
C19 C18 1.3908(17) . ?
C19 C20 1.3953(16) . ?
C19 C22 1.4394(16) . ?
C14 C15 1.2008(17) . ?
C14 C12 1.4266(16) . ?
C18 H18 0.9500 . ?
C18 C17 1.3804(17) . ?
C13 H13 0.9500 . ?
C13 C12 1.3973(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3991(17) . ?
C17 H17 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.3770(16) . ?
C21 H21 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5180(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C1 1.5122(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5073(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 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
C4 N5 C6 122.59(10) . . ?
C4 N5 C7 121.24(9) . . ?
C7 N5 C6 114.16(10) . . ?
N5 C4 C3 119.98(10) . . ?
N5 C4 C10 120.82(10) . . ?
C10 C4 C3 119.18(10) . . ?
C4 C3 C2 117.81(10) . . ?
C13 C3 C4 119.80(10) . . ?
C13 C3 C2 122.37(11) . . ?
C4 C10 C9 119.77(10) . . ?
C11 C10 C4 119.14(10) . . ?
C11 C10 C9 121.08(10) . . ?
C17 C16 C15 121.13(11) . . ?
C21 C16 C17 118.93(11) . . ?
C21 C16 C15 119.93(11) . . ?
C18 C19 C20 120.17(11) . . ?
C18 C19 C22 119.49(11) . . ?
C20 C19 C22 120.33(11) . . ?
C15 C14 C12 176.37(13) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.83(11) . . ?
C17 C18 H18 120.1 . . ?
C3 C13 H13 119.2 . . ?
C3 C13 C12 121.54(11) . . ?
C12 C13 H13 119.2 . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.34(11) . . ?
C12 C11 H11 118.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.58(11) . . ?
C18 C17 H17 119.7 . . ?
C14 C15 C16 176.95(13) . . ?
C13 C12 C14 122.16(11) . . ?
C13 C12 C11 117.86(10) . . ?
C11 C12 C14 119.95(11) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.58(11) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.89(11) . . ?
C20 C21 H21 119.6 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C3 C2 C1 108.90(10) . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
N23 C22 C19 179.00(14) . . ?
N5 C6 H6A 109.0 . . ?
N5 C6 H6B 109.0 . . ?
N5 C6 C1 113.01(10) . . ?
H6A C6 H6B 107.8 . . ?
C1 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
C6 C1 C2 109.90(10) . . ?
C6 C1 H1A 109.7 . . ?
C6 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 C8 110.52(10) . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
N5 C7 H7A 109.3 . . ?
N5 C7 H7B 109.3 . . ?
N5 C7 C8 111.66(11) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C9 C8 C7 109.94(12) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?

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
N5 C4 C3 C13 -177.60(10) . . . . ?
N5 C4 C3 C2 0.74(16) . . . . ?
N5 C4 C10 C11 -179.78(10) . . . . ?
N5 C4 C10 C9 1.20(17) . . . . ?
N5 C6 C1 C2 -44.99(14) . . . . ?
N5 C7 C8 C9 -55.32(16) . . . . ?
C4 N5 C6 C1 6.96(16) . . . . ?
C4 N5 C7 C8 29.71(16) . . . . ?
C4 C3 C13 C12 -3.34(17) . . . . ?
C4 C3 C2 C1 -38.54(14) . . . . ?
C4 C10 C11 C12 -1.96(17) . . . . ?
C4 C10 C9 C8 -27.71(17) . . . . ?
C3 C4 C10 C11 -1.40(16) . . . . ?
C3 C4 C10 C9 179.58(11) . . . . ?
C3 C13 C12 C14 177.98(11) . . . . ?
C3 C13 C12 C11 0.04(17) . . . . ?
C3 C2 C1 C6 59.78(13) . . . . ?
C10 C4 C3 C13 4.01(16) . . . . ?
C10 C4 C3 C2 -177.65(11) . . . . ?
C10 C11 C12 C14 -175.31(11) . . . . ?
C10 C11 C12 C13 2.67(17) . . . . ?
C10 C9 C8 C7 53.70(16) . . . . ?
C19 C18 C17 C16 0.42(18) . . . . ?
C19 C20 C21 C16 0.28(19) . . . . ?
C18 C19 C20 C21 -1.09(18) . . . . ?
C13 C3 C2 C1 139.76(11) . . . . ?
C11 C10 C9 C8 153.29(12) . . . . ?
C17 C16 C21 C20 0.85(18) . . . . ?
C15 C16 C17 C18 177.57(11) . . . . ?
C15 C16 C21 C20 -177.93(11) . . . . ?
C20 C19 C18 C17 0.74(18) . . . . ?
C21 C16 C17 C18 -1.20(18) . . . . ?
C2 C3 C13 C12 178.40(11) . . . . ?
C22 C19 C18 C17 179.77(11) . . . . ?
C22 C19 C20 C21 179.89(11) . . . . ?
C6 N5 C4 C3 16.53(16) . . . . ?
C6 N5 C4 C10 -165.10(11) . . . . ?
C6 N5 C7 C8 -166.02(11) . . . . ?
C9 C10 C11 C12 177.04(11) . . . . ?
C7 N5 C4 C3 179.45(11) . . . . ?
C7 N5 C4 C10 -2.18(16) . . . . ?
C7 N5 C6 C1 -157.06(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.759
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and CH2Cl2'
_chemical_properties_physical    
Oxygen-sensitive,Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_tmejld-h_auto
_database_code_depnum_ccdc_archive 'CCDC 2401629'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Ibaraki University
Japan
;
_audit_update_record             
;
2024-11-11 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT360_tmejld-h_auto       
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C1       - C23      .       1.30 Ang.
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT410_tmejld-h_auto       
;
PROBLEM: Short Intra H...H Contact  H1A      ..H23B     .       1.86 Ang.
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
# Added during the CSD deposition process: Monday 11 November 2024 01:55 AM
# end Validation Reply Form

_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            TMeJLD-H
_chemical_name_systematic        
9-[2-(4-Cyanophenyl)ethyn-1-yl]-1,1,7,7-tetramethyljulolidine
_chemical_formula_moiety         'C25 H26 N2'
_chemical_formula_sum            'C25 H26 N2'
_chemical_formula_weight         354.48
_chemical_absolute_configuration .
_chemical_melting_point          '192.2--193.4 ?C'
_chemical_oxdiff_formula         C25H26N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.4085(10)
_cell_length_b                   6.3801(3)
_cell_length_c                   33.690(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3956.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7169
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.5760
_cell_measurement_theta_min      3.2340
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 3 -41 0.0815
-8 -7 -27 0.1045
3 -8 17 0.0966
11 -3 41 0.0785
7 7 24 0.1189
-16 4 -32 0.0931
-23 0 23 0.0315
25 -2 0 0.0409
25 2 0 0.0659
4 0 -47 0.0820

_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.113
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.5816 2.7958 -40.7920 -0.1009 0.0450 0.9939
-8.1838 -6.8475 -26.8974 -0.8788 0.3915 0.2728
3.4406 -8.3019 17.0799 -0.6243 0.2781 -0.7300
10.6006 -2.7597 40.8441 0.1047 -0.0467 -0.9934
7.3464 7.3868 23.5050 0.8991 -0.4006 -0.1766
-15.6797 3.6995 -32.4428 -0.1047 -0.2356 0.9662
-22.7717 0.2195 22.7872 -0.4065 -0.9124 -0.0477
25.2381 -2.1223 0.2330 0.3578 0.8033 -0.4762
25.4769 1.7282 -0.1514 0.7100 0.6391 -0.2956
4.4474 0.4983 -46.7239 0.0003 0.6404 0.7681

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            28595
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.861
_diffrn_ambient_temperature      173
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   6.00   0.50    4.53    --    5.00  34.00  14.00   50
  2  ω    -38.00 -13.00   0.50    4.53    --  -13.20  34.00  14.00   50
  3  ω     24.00  50.00   0.50    4.53    --    5.00   0.00-180.00   52
  4  ω   -103.00  75.00   0.50    4.53    --  -13.20  28.00-120.00  356
  5  ω    -62.00   6.00   0.50    4.53    --  -13.20  46.00 -60.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0217532000
_diffrn_orient_matrix_UB_12      0.0904437000
_diffrn_orient_matrix_UB_13      0.0030283000
_diffrn_orient_matrix_UB_21      0.0281054000
_diffrn_orient_matrix_UB_22      -0.0455361000
_diffrn_orient_matrix_UB_23      -0.0115154000
_diffrn_orient_matrix_UB_31      -0.0148324000
_diffrn_orient_matrix_UB_32      0.0460747000
_diffrn_orient_matrix_UB_33      -0.0173592000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                5443
_reflns_number_total             7972
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7972
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1129P)²+1.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C21(H21A,H21B), C1(H1A,H1B), C20(H20A,H20B), C33(H33A,H33B),
 C52(H52A,H52B), C34(H34A,H34B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C44(H44), C12(H12), C8(H8), C6(H6), C15(H15), C43(H43), C37(H37),
 C47(H47), C16(H16), C46(H46), C39(H39)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C53(H53A,H53B,H53C), C54(H54A,
 H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N22 N 0.4892(2) 1.6541(7) 0.68115(13) 0.0494(11) Uani 1 1 d . . . . .
C45 C 0.5180(3) 0.7317(7) 0.48014(15) 0.0391(11) Uani 1 1 d . . . . .
C11 C 0.6516(3) 0.6187(7) 0.56547(14) 0.0386(11) Uani 1 1 d . . . . .
C10 C 0.6161(3) 0.7777(8) 0.58776(16) 0.0451(13) Uani 1 1 d . . . . .
N49 N 0.4529(3) 1.0220(8) 0.52008(16) 0.0598(12) Uani 1 1 d . . . . .
C13 C 0.6517(3) 0.2818(8) 0.53290(19) 0.0499(14) Uani 1 1 d . . . . .
H13 H 0.627169 0.156157 0.525879 0.060 Uiso 1 1 calc R U . . .
C23 C 0.5336(4) 1.7608(9) 0.70815(18) 0.0535(15) Uani 1 1 d . . . . .
H23A H 0.542580 1.901811 0.696914 0.064 Uiso 1 1 calc R U . . .
H23B H 0.504663 1.781345 0.732600 0.064 Uiso 1 1 calc R U . . .
C48 C 0.4823(3) 0.8920(9) 0.50278(16) 0.0454(12) Uani 1 1 d . . . . .
C44 C 0.4822(3) 0.5482(8) 0.47135(16) 0.0470(13) Uani 1 1 d . . . . .
H44 H 0.434056 0.527285 0.480637 0.056 Uiso 1 1 calc R U . . .
C14 C 0.7235(3) 0.3121(8) 0.52165(15) 0.0417(12) Uani 1 1 d . . . . .
N18 N 0.7900(3) 0.0263(9) 0.48183(17) 0.0691(15) Uani 1 1 d . . . . .
N32 N 0.7633(3) -0.5810(8) 0.31543(15) 0.0623(14) Uani 1 1 d . . . . .
C4 C 0.5127(3) 1.4686(7) 0.66327(14) 0.0378(11) Uani 1 1 d . . . . .
C3 C 0.5807(3) 1.3833(8) 0.67385(14) 0.0403(11) Uani 1 1 d . . . . .
C21 C 0.4231(3) 1.7450(9) 0.67039(18) 0.0559(15) Uani 1 1 d . . . . .
H21A H 0.395418 1.767612 0.695203 0.067 Uiso 1 1 calc R U . . .
H21B H 0.434343 1.885500 0.659534 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6161(3) 0.4345(8) 0.55425(16) 0.0462(13) Uani 1 1 d . . . . .
H12 H 0.566717 0.414281 0.561467 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6036(3) 1.2030(8) 0.65513(15) 0.0441(12) Uani 1 1 d . . . . .
H8 H 0.649602 1.145697 0.661938 0.053 Uiso 1 1 calc R U . . .
C42 C 0.5864(3) 0.4251(8) 0.43543(15) 0.0439(12) Uani 1 1 d . . . . .
C5 C 0.4686(2) 1.3675(7) 0.63489(15) 0.0385(11) Uani 1 1 d . . . . .
C36 C 0.7768(3) -0.3027(9) 0.36409(16) 0.0476(13) Uani 1 1 d . . . . .
C7 C 0.5616(3) 1.1021(7) 0.62658(15) 0.0405(11) Uani 1 1 d . . . . .
C6 C 0.4936(3) 1.1835(7) 0.61757(14) 0.0400(11) Uani 1 1 d . . . . .
H6 H 0.463439 1.111629 0.599164 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5890(3) 0.9203(8) 0.60593(16) 0.0466(12) Uani 1 1 d . . . . .
C15 C 0.7585(3) 0.4952(9) 0.5314(2) 0.0602(16) Uani 1 1 d . . . . .
H15 H 0.806892 0.519003 0.522795 0.072 Uiso 1 1 calc R U . . .
C43 C 0.5157(3) 0.3942(8) 0.44917(17) 0.0485(13) Uani 1 1 d . . . . .
H43 H 0.490771 0.267694 0.443279 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3963(3) 1.4604(9) 0.62056(17) 0.0503(13) Uani 1 1 d . . . . .
C37 C 0.7481(3) -0.1274(8) 0.38217(16) 0.0468(12) Uani 1 1 d . . . . .
H37 H 0.775784 -0.058129 0.402044 0.056 Uiso 1 1 calc R U . . .
C2 C 0.6308(3) 1.4862(8) 0.70464(16) 0.0474(13) Uani 1 1 d . . . . .
C47 C 0.6220(3) 0.6086(8) 0.44490(17) 0.0509(13) Uani 1 1 d . . . . .
H47 H 0.670629 0.628788 0.436189 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7230(3) 0.6443(9) 0.5539(2) 0.0596(16) Uani 1 1 d . . . . .
H16 H 0.748261 0.767646 0.561545 0.072 Uiso 1 1 calc R U . . .
C46 C 0.5886(3) 0.7622(8) 0.46664(18) 0.0519(14) Uani 1 1 d . . . . .
H46 H 0.613540 0.888871 0.472476 0.062 Uiso 1 1 calc R U . . .
C38 C 0.6799(3) -0.0485(9) 0.37221(16) 0.0549(14) Uani 1 1 d . . . . .
C30 C 0.6683(3) -0.3172(8) 0.32240(16) 0.0508(13) Uani 1 1 d . . . . .
C40 C 0.6488(3) 0.1252(9) 0.39370(18) 0.0572(15) Uani 1 1 d . . . . .
C17 C 0.7603(3) 0.1516(9) 0.49916(17) 0.0502(13) Uani 1 1 d . . . . .
C31 C 0.7359(3) -0.3984(9) 0.33399(16) 0.0503(13) Uani 1 1 d . . . . .
C1 C 0.5963(4) 1.6867(10) 0.7191(2) 0.0658(17) Uani 1 1 d . . . . .
H1A H 0.593932 1.674277 0.748327 0.079 Uiso 1 1 calc R U . . .
H1B H 0.631987 1.798922 0.713420 0.079 Uiso 1 1 calc R U . . .
C41 C 0.6212(3) 0.2627(8) 0.41238(18) 0.0508(14) Uani 1 1 d . . . . .
C35 C 0.8483(3) -0.3894(10) 0.37874(18) 0.0579(15) Uani 1 1 d . . . . .
C39 C 0.6423(3) -0.1441(10) 0.34204(18) 0.0592(15) Uani 1 1 d . . . . .
H39 H 0.596461 -0.088415 0.334469 0.071 Uiso 1 1 calc R U . . .
C20 C 0.3783(4) 1.6528(13) 0.6448(2) 0.088(2) Uani 1 1 d . . . . .
H20A H 0.363955 1.762448 0.625574 0.106 Uiso 1 1 calc R U . . .
H20B H 0.333917 1.617576 0.660074 0.106 Uiso 1 1 calc R U . . .
C29 C 0.6221(4) -0.4192(11) 0.2893(2) 0.0701(19) Uani 1 1 d . . . . .
C27 C 0.6409(4) 1.3411(11) 0.7395(2) 0.080(2) Uani 1 1 d . . . . .
H27A H 0.668876 1.412563 0.760225 0.120 Uiso 1 1 calc R U . . .
H27B H 0.666993 1.215176 0.730933 0.120 Uiso 1 1 calc R U . . .
H27C H 0.593230 1.301160 0.750084 0.120 Uiso 1 1 calc R U . . .
C33 C 0.8272(4) -0.6723(10) 0.3296(2) 0.0668(18) Uani 1 1 d . . . . .
H33A H 0.812996 -0.796481 0.345448 0.080 Uiso 1 1 calc R U . . .
H33B H 0.854458 -0.724656 0.306337 0.080 Uiso 1 1 calc R U . . .
C26 C 0.7029(4) 1.5469(14) 0.6853(2) 0.083(2) Uani 1 1 d . . . . .
H26A H 0.693501 1.637364 0.662322 0.125 Uiso 1 1 calc R U . . .
H26B H 0.728278 1.420052 0.676523 0.125 Uiso 1 1 calc R U . . .
H26C H 0.733052 1.622197 0.704525 0.125 Uiso 1 1 calc R U . . .
C50 C 0.8422(4) -0.4650(13) 0.4205(2) 0.079(2) Uani 1 1 d . . . . .
H50A H 0.888085 -0.530656 0.428510 0.118 Uiso 1 1 calc R U . . .
H50B H 0.802834 -0.567734 0.422409 0.118 Uiso 1 1 calc R U . . .
H50C H 0.831835 -0.346160 0.438049 0.118 Uiso 1 1 calc R U . . .
C51 C 0.9082(4) -0.2180(15) 0.3762(3) 0.098(3) Uani 1 1 d . . . . .
H51A H 0.892728 -0.094167 0.391213 0.147 Uiso 1 1 calc R U . . .
H51B H 0.916002 -0.179427 0.348389 0.147 Uiso 1 1 calc R U . . .
H51C H 0.953496 -0.272440 0.387458 0.147 Uiso 1 1 calc R U . . .
C25 C 0.4050(4) 1.5267(12) 0.5777(2) 0.073(2) Uani 1 1 d . . . . .
H25A H 0.445745 1.624735 0.575483 0.109 Uiso 1 1 calc R U . . .
H25B H 0.360318 1.595240 0.568672 0.109 Uiso 1 1 calc R U . . .
H25C H 0.414498 1.402993 0.561287 0.109 Uiso 1 1 calc R U . . .
C52 C 0.7190(4) -0.6872(11) 0.2882(2) 0.074(2) Uani 1 1 d . . . . .
H52A H 0.751075 -0.739382 0.266826 0.089 Uiso 1 1 calc R U . . .
H52B H 0.699561 -0.812080 0.302071 0.089 Uiso 1 1 calc R U . . .
C24 C 0.3359(4) 1.2999(13) 0.6250(3) 0.092(3) Uani 1 1 d . . . . .
H24A H 0.344204 1.183706 0.606547 0.138 Uiso 1 1 calc R U . . .
H24B H 0.289099 1.365966 0.619135 0.138 Uiso 1 1 calc R U . . .
H24C H 0.335536 1.246382 0.652297 0.138 Uiso 1 1 calc R U . . .
C34 C 0.8736(4) -0.5603(15) 0.3517(3) 0.110(3) Uani 1 1 d . . . . .
H34A H 0.909085 -0.496616 0.333200 0.132 Uiso 1 1 calc R U . . .
H34B H 0.900948 -0.661306 0.368273 0.132 Uiso 1 1 calc R U . . .
C53 C 0.5543(5) -0.5048(18) 0.3058(3) 0.128(4) Uani 1 1 d . . . . .
H53A H 0.520732 -0.389695 0.311698 0.192 Uiso 1 1 calc R U . . .
H53B H 0.565014 -0.581988 0.330268 0.192 Uiso 1 1 calc R U . . .
H53C H 0.532002 -0.599666 0.286453 0.192 Uiso 1 1 calc R U . . .
C54 C 0.6041(7) -0.2576(15) 0.2579(3) 0.120(4) Uani 1 1 d . . . . .
H54A H 0.578988 -0.325802 0.235732 0.180 Uiso 1 1 calc R U . . .
H54B H 0.649063 -0.192885 0.248251 0.180 Uiso 1 1 calc R U . . .
H54C H 0.572629 -0.149462 0.269334 0.180 Uiso 1 1 calc R U . . .
C28 C 0.6628(5) -0.5928(16) 0.2707(3) 0.119(4) Uani 1 1 d . . . . .
H28A H 0.626919 -0.703787 0.264643 0.143 Uiso 1 1 calc R U . . .
H28B H 0.680696 -0.539759 0.244877 0.143 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N22 C23 1.399(7) . ?
N22 C4 1.397(6) . ?
N22 C21 1.395(7) . ?
C45 C48 1.434(8) . ?
C45 C44 1.375(7) . ?
C45 C46 1.392(7) . ?
C11 C10 1.421(7) . ?
C11 C12 1.397(7) . ?
C11 C16 1.380(7) . ?
C10 C9 1.204(7) . ?
N49 C48 1.149(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(7) . ?
C13 C12 1.377(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C1 1.300(8) . ?
C44 H44 0.9500 . ?
C44 C43 1.380(7) . ?
C14 C15 1.374(7) . ?
C14 C17 1.443(7) . ?
N18 C17 1.130(7) . ?
N32 C31 1.415(7) . ?
N32 C33 1.397(8) . ?
N32 C52 1.402(8) . ?
C4 C3 1.410(7) . ?
C4 C5 1.410(7) . ?
C3 C8 1.379(7) . ?
C3 C2 1.536(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.330(10) . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.392(7) . ?
C42 C43 1.395(7) . ?
C42 C47 1.379(8) . ?
C42 C41 1.444(8) . ?
C5 C6 1.389(7) . ?
C5 C19 1.536(7) . ?
C36 C37 1.378(7) . ?
C36 C31 1.403(8) . ?
C36 C35 1.511(8) . ?
C7 C6 1.390(7) . ?
C7 C9 1.443(7) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.380(8) . ?
C43 H43 0.9500 . ?
C19 C20 1.512(9) . ?
C19 C25 1.512(9) . ?
C19 C24 1.519(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.394(8) . ?
C2 C1 1.509(8) . ?
C2 C27 1.508(9) . ?
C2 C26 1.528(9) . ?
C47 H47 0.9500 . ?
C47 C46 1.369(8) . ?
C16 H16 0.9500 . ?
C46 H46 0.9500 . ?
C38 C40 1.442(8) . ?
C38 C39 1.373(8) . ?
C30 C31 1.404(8) . ?
C30 C39 1.374(8) . ?
C30 C29 1.545(8) . ?
C40 C41 1.193(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C35 C50 1.492(9) . ?
C35 C51 1.554(10) . ?
C35 C34 1.495(9) . ?
C39 H39 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C29 C53 1.472(11) . ?
C29 C54 1.515(11) . ?
C29 C28 1.477(10) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.340(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 C28 1.334(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
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
C4 N22 C23 120.7(5) . . ?
C21 N22 C23 118.4(5) . . ?
C21 N22 C4 120.7(5) . . ?
C44 C45 C48 120.2(5) . . ?
C44 C45 C46 119.7(5) . . ?
C46 C45 C48 120.1(5) . . ?
C12 C11 C10 121.9(4) . . ?
C16 C11 C10 120.2(5) . . ?
C16 C11 C12 117.9(5) . . ?
C9 C10 C11 176.2(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(5) . . ?
N22 C23 H23A 106.9 . . ?
N22 C23 H23B 106.9 . . ?
H23A C23 H23B 106.7 . . ?
C1 C23 N22 121.7(5) . . ?
C1 C23 H23A 106.9 . . ?
C1 C23 H23B 106.9 . . ?
N49 C48 C45 178.3(6) . . ?
C45 C44 H44 119.7 . . ?
C45 C44 C43 120.6(5) . . ?
C43 C44 H44 119.7 . . ?
C13 C14 C17 119.5(5) . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 C17 120.6(5) . . ?
C33 N32 C31 119.5(5) . . ?
C33 N32 C52 120.8(5) . . ?
C52 N32 C31 118.6(5) . . ?
N22 C4 C3 119.5(5) . . ?
N22 C4 C5 120.1(4) . . ?
C3 C4 C5 120.4(4) . . ?
C4 C3 C2 122.6(4) . . ?
C8 C3 C4 118.6(5) . . ?
C8 C3 C2 118.8(4) . . ?
N22 C21 H21A 106.9 . . ?
N22 C21 H21B 106.9 . . ?
H21A C21 H21B 106.7 . . ?
C20 C21 N22 121.7(6) . . ?
C20 C21 H21A 106.9 . . ?
C20 C21 H21B 106.9 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C3 C8 H8 118.9 . . ?
C3 C8 C7 122.2(5) . . ?
C7 C8 H8 118.9 . . ?
C43 C42 C41 119.4(5) . . ?
C47 C42 C43 119.1(5) . . ?
C47 C42 C41 121.5(5) . . ?
C4 C5 C19 122.4(4) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 C19 118.7(5) . . ?
C37 C36 C31 117.9(5) . . ?
C37 C36 C35 119.1(5) . . ?
C31 C36 C35 123.0(5) . . ?
C8 C7 C9 120.7(4) . . ?
C6 C7 C8 118.6(4) . . ?
C6 C7 C9 120.7(5) . . ?
C5 C6 C7 121.5(5) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C10 C9 C7 175.2(6) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(5) . . ?
C16 C15 H15 120.2 . . ?
C44 C43 C42 119.7(5) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C20 C19 C5 109.5(5) . . ?
C20 C19 C25 108.2(5) . . ?
C20 C19 C24 109.5(6) . . ?
C25 C19 C5 108.4(4) . . ?
C25 C19 C24 111.1(6) . . ?
C24 C19 C5 110.1(5) . . ?
C36 C37 H37 119.0 . . ?
C36 C37 C38 122.1(5) . . ?
C38 C37 H37 119.0 . . ?
C1 C2 C3 109.1(4) . . ?
C1 C2 C26 106.8(5) . . ?
C27 C2 C3 109.7(5) . . ?
C27 C2 C1 108.7(5) . . ?
C27 C2 C26 112.5(6) . . ?
C26 C2 C3 110.0(5) . . ?
C42 C47 H47 119.4 . . ?
C46 C47 C42 121.2(5) . . ?
C46 C47 H47 119.4 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.6(5) . . ?
C15 C16 H16 119.2 . . ?
C45 C46 H46 120.2 . . ?
C47 C46 C45 119.7(5) . . ?
C47 C46 H46 120.2 . . ?
C37 C38 C40 121.0(5) . . ?
C39 C38 C37 118.2(5) . . ?
C39 C38 C40 120.8(5) . . ?
C31 C30 C29 122.2(5) . . ?
C39 C30 C31 118.2(5) . . ?
C39 C30 C29 119.6(5) . . ?
C41 C40 C38 177.1(7) . . ?
N18 C17 C14 179.1(7) . . ?
C36 C31 N32 119.1(5) . . ?
C36 C31 C30 121.0(5) . . ?
C30 C31 N32 119.8(5) . . ?
C23 C1 C2 126.2(6) . . ?
C23 C1 H1A 105.8 . . ?
C23 C1 H1B 105.8 . . ?
C2 C1 H1A 105.8 . . ?
C2 C1 H1B 105.8 . . ?
H1A C1 H1B 106.2 . . ?
C40 C41 C42 178.4(7) . . ?
C36 C35 C51 110.0(5) . . ?
C50 C35 C36 111.2(5) . . ?
C50 C35 C51 109.4(6) . . ?
C50 C35 C34 111.2(6) . . ?
C34 C35 C36 109.8(5) . . ?
C34 C35 C51 105.0(6) . . ?
C38 C39 C30 122.5(5) . . ?
C38 C39 H39 118.7 . . ?
C30 C39 H39 118.7 . . ?
C21 C20 C19 124.9(6) . . ?
C21 C20 H20A 106.1 . . ?
C21 C20 H20B 106.1 . . ?
C19 C20 H20A 106.1 . . ?
C19 C20 H20B 106.1 . . ?
H20A C20 H20B 106.3 . . ?
C53 C29 C30 110.5(6) . . ?
C53 C29 C54 109.3(8) . . ?
C53 C29 C28 108.2(8) . . ?
C54 C29 C30 109.8(6) . . ?
C28 C29 C30 110.1(6) . . ?
C28 C29 C54 108.9(7) . . ?
C2 C27 H27A 109.5 . . ?
C2 C27 H27B 109.5 . . ?
C2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N32 C33 H33A 107.2 . . ?
N32 C33 H33B 107.2 . . ?
H33A C33 H33B 106.9 . . ?
C34 C33 N32 120.3(6) . . ?
C34 C33 H33A 107.2 . . ?
C34 C33 H33B 107.2 . . ?
C2 C26 H26A 109.5 . . ?
C2 C26 H26B 109.5 . . ?
C2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C35 C50 H50A 109.5 . . ?
C35 C50 H50B 109.5 . . ?
C35 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C35 C51 H51A 109.5 . . ?
C35 C51 H51B 109.5 . . ?
C35 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N32 C52 H52A 107.0 . . ?
N32 C52 H52B 107.0 . . ?
H52A C52 H52B 106.7 . . ?
C28 C52 N32 121.5(6) . . ?
C28 C52 H52A 107.0 . . ?
C28 C52 H52B 107.0 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C35 C34 H34A 106.9 . . ?
C35 C34 H34B 106.9 . . ?
C33 C34 C35 121.9(6) . . ?
C33 C34 H34A 106.9 . . ?
C33 C34 H34B 106.9 . . ?
H34A C34 H34B 106.7 . . ?
C29 C53 H53A 109.5 . . ?
C29 C53 H53B 109.5 . . ?
C29 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C29 C54 H54A 109.5 . . ?
C29 C54 H54B 109.5 . . ?
C29 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C29 C28 H28A 106.6 . . ?
C29 C28 H28B 106.6 . . ?
C52 C28 C29 122.9(7) . . ?
C52 C28 H28A 106.6 . . ?
C52 C28 H28B 106.6 . . ?
H28A C28 H28B 106.6 . . ?

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
N22 C23 C1 C2 1.3(10) . . . . ?
N22 C4 C3 C8 -178.4(4) . . . . ?
N22 C4 C3 C2 0.1(7) . . . . ?
N22 C4 C5 C6 179.9(4) . . . . ?
N22 C4 C5 C19 3.7(7) . . . . ?
N22 C21 C20 C19 -8.7(12) . . . . ?
C45 C44 C43 C42 -0.2(8) . . . . ?
C10 C11 C12 C13 -179.5(5) . . . . ?
C10 C11 C16 C15 -178.5(6) . . . . ?
C13 C14 C15 C16 2.8(9) . . . . ?
C23 N22 C4 C3 2.7(7) . . . . ?
C23 N22 C4 C5 -177.4(4) . . . . ?
C23 N22 C21 C20 179.9(6) . . . . ?
C48 C45 C44 C43 179.2(5) . . . . ?
C48 C45 C46 C47 -179.7(5) . . . . ?
C44 C45 C46 C47 -0.3(8) . . . . ?
C14 C13 C12 C11 -1.2(9) . . . . ?
C14 C15 C16 C11 -2.8(10) . . . . ?
N32 C33 C34 C35 31.5(13) . . . . ?
N32 C52 C28 C29 -28.5(15) . . . . ?
C4 N22 C23 C1 -3.5(8) . . . . ?
C4 N22 C21 C20 4.3(9) . . . . ?
C4 C3 C8 C7 -0.7(7) . . . . ?
C4 C3 C2 C1 -1.9(7) . . . . ?
C4 C3 C2 C27 117.1(6) . . . . ?
C4 C3 C2 C26 -118.7(6) . . . . ?
C4 C5 C6 C7 -2.3(7) . . . . ?
C4 C5 C19 C20 -6.7(7) . . . . ?
C4 C5 C19 C25 111.1(6) . . . . ?
C4 C5 C19 C24 -127.1(6) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C3 C4 C5 C19 -176.4(4) . . . . ?
C3 C8 C7 C6 -1.8(7) . . . . ?
C3 C8 C7 C9 176.5(5) . . . . ?
C3 C2 C1 C23 1.3(9) . . . . ?
C21 N22 C23 C1 -179.1(6) . . . . ?
C21 N22 C4 C3 178.2(5) . . . . ?
C21 N22 C4 C5 -1.9(7) . . . . ?
C12 C11 C16 C15 0.9(9) . . . . ?
C12 C13 C14 C15 -0.8(9) . . . . ?
C12 C13 C14 C17 -179.8(5) . . . . ?
C8 C3 C2 C1 176.6(5) . . . . ?
C8 C3 C2 C27 -64.5(6) . . . . ?
C8 C3 C2 C26 59.8(7) . . . . ?
C8 C7 C6 C5 3.3(7) . . . . ?
C42 C47 C46 C45 1.3(9) . . . . ?
C5 C4 C3 C8 1.7(7) . . . . ?
C5 C4 C3 C2 -179.8(4) . . . . ?
C5 C19 C20 C21 9.3(10) . . . . ?
C36 C37 C38 C40 175.1(5) . . . . ?
C36 C37 C38 C39 -3.2(9) . . . . ?
C36 C35 C34 C33 -25.4(12) . . . . ?
C6 C5 C19 C20 177.1(5) . . . . ?
C6 C5 C19 C25 -65.0(6) . . . . ?
C6 C5 C19 C24 56.8(7) . . . . ?
C9 C7 C6 C5 -174.9(5) . . . . ?
C43 C42 C47 C46 -1.6(8) . . . . ?
C19 C5 C6 C7 174.0(4) . . . . ?
C37 C36 C31 N32 -178.8(5) . . . . ?
C37 C36 C31 C30 0.5(8) . . . . ?
C37 C36 C35 C50 63.9(7) . . . . ?
C37 C36 C35 C51 -57.4(8) . . . . ?
C37 C36 C35 C34 -172.5(6) . . . . ?
C37 C38 C39 C30 2.1(9) . . . . ?
C2 C3 C8 C7 -179.2(5) . . . . ?
C47 C42 C43 C44 1.1(8) . . . . ?
C16 C11 C12 C13 1.1(8) . . . . ?
C46 C45 C44 C43 -0.2(8) . . . . ?
C30 C29 C28 C52 19.8(14) . . . . ?
C40 C38 C39 C30 -176.2(6) . . . . ?
C17 C14 C15 C16 -178.2(6) . . . . ?
C31 N32 C33 C34 -20.2(11) . . . . ?
C31 N32 C52 C28 20.2(12) . . . . ?
C31 C36 C37 C38 1.9(8) . . . . ?
C31 C36 C35 C50 -112.9(7) . . . . ?
C31 C36 C35 C51 125.7(7) . . . . ?
C31 C36 C35 C34 10.6(9) . . . . ?
C31 C30 C39 C38 0.2(9) . . . . ?
C31 C30 C29 C53 114.1(8) . . . . ?
C31 C30 C29 C54 -125.3(7) . . . . ?
C31 C30 C29 C28 -5.4(10) . . . . ?
C41 C42 C43 C44 179.7(5) . . . . ?
C41 C42 C47 C46 179.8(5) . . . . ?
C35 C36 C37 C38 -175.1(5) . . . . ?
C35 C36 C31 N32 -1.9(8) . . . . ?
C35 C36 C31 C30 177.4(5) . . . . ?
C39 C30 C31 N32 177.7(5) . . . . ?
C39 C30 C31 C36 -1.6(8) . . . . ?
C39 C30 C29 C53 -64.3(9) . . . . ?
C39 C30 C29 C54 56.3(9) . . . . ?
C39 C30 C29 C28 176.2(7) . . . . ?
C29 C30 C31 N32 -0.7(8) . . . . ?
C29 C30 C31 C36 179.9(6) . . . . ?
C29 C30 C39 C38 178.7(6) . . . . ?
C27 C2 C1 C23 -118.3(8) . . . . ?
C33 N32 C31 C36 5.4(8) . . . . ?
C33 N32 C31 C30 -173.9(6) . . . . ?
C33 N32 C52 C28 -171.7(8) . . . . ?
C26 C2 C1 C23 120.1(7) . . . . ?
C50 C35 C34 C33 98.2(10) . . . . ?
C51 C35 C34 C33 -143.6(9) . . . . ?
C25 C19 C20 C21 -108.7(8) . . . . ?
C52 N32 C31 C36 173.7(6) . . . . ?
C52 N32 C31 C30 -5.6(8) . . . . ?
C52 N32 C33 C34 171.8(8) . . . . ?
C24 C19 C20 C21 130.1(8) . . . . ?
C53 C29 C28 C52 -101.1(11) . . . . ?
C54 C29 C28 C52 140.2(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.811
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and CH2Cl2'
_chemical_properties_physical    
Oxygen-sensitive,Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_tmejld-f_auto
_database_code_depnum_ccdc_archive 'CCDC 2402070'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Ibaraki University
Japan
;
_audit_update_record             
;
2024-11-12 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_tmejld-f_auto       
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT029_tmejld-f_auto       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.912 Why?
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT031_tmejld-f_auto       
;
PROBLEM: Refined Extinction Parameter Within Range of ...      0.500 Sigma
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT080_tmejld-f_auto       
;
PROBLEM: Maximum Shift/Error ............................       1.15 Why ?
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT082_tmejld-f_auto       
;
PROBLEM: High R1 Value ..................................       0.30 Report
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT084_tmejld-f_auto       
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.71 Report
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT097_tmejld-f_auto       
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.88 eA-3
RESPONSE: This is because diffraction is much weaker.
;
_vrf_PLAT211_tmejld-f_auto       
;
PROBLEM: ADP of Atom C21       is N.P.D. or (nearly) 2D .     Please Check
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT213_tmejld-f_auto       
;
PROBLEM: Atom N11             has ADP max/min Ratio .....       14.1 oblate
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT934_tmejld-f_auto       
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..         24 Check
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT110_tmejld-f_auto       
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT112_tmejld-f_auto       
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         A        100 %Fit
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT113_tmejld-f_auto       
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT213_tmejld-f_auto_2     
;
PROBLEM: Atom C00O            has ADP max/min Ratio .....        5.0 prolat
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT340_tmejld-f_auto       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01654 Ang.
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
_vrf_PLAT911_tmejld-f_auto       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        651 Report
RESPONSE: This is attributed to the shorter X-ray exposure time due to the low photostability of the compound.
;
# Added during the CSD deposition process: Tuesday 12 November 2024 05:36 AM
# end Validation Reply Form

_audit_creation_date             2024-11-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 F4 N2'
_chemical_formula_sum            'C25 H22 F4 N2'
_chemical_formula_weight         426.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H22F4N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3253(5)
_cell_length_b                   16.5547(18)
_cell_length_c                   21.013(3)
_cell_angle_alpha                70.720(11)
_cell_angle_beta                 89.417(9)
_cell_angle_gamma                89.860(8)
_cell_volume                     2076.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2635
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.0610
_cell_measurement_theta_min      3.1940
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 23 8 0.0792
9 0 -4 0.1021
1 -23 -8 0.0795
-9 -1 4 0.1040
1 1 -27 0.0196
-1 -1 27 0.0225
3 1 26 0.0466

_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0380 23.2800 7.7595 -0.1558 -0.0694 0.9853
8.8050 -0.4418 -4.3036 -0.8993 -0.4001 -0.1763
1.4643 -22.9911 -8.3721 -0.0000 0.0001 -1.0000
-8.7863 -1.3297 3.7030 0.9090 0.4044 0.1009
1.2253 1.3356 -27.0523 0.1040 -0.9916 0.0765
-1.2412 -1.1013 27.1577 -0.1041 0.9924 -0.0663
3.2726 0.8874 26.4628 -0.5864 0.8075 -0.0640

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.912
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16845
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.922
_diffrn_ambient_temperature      173
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00   5.00   0.50    2.88    --  -13.20  55.00 -90.00  216
  2  ω     35.00  76.00   0.50    2.88    --  -13.20  55.00 -90.00   82
  3  ω    -26.00  75.00   0.50    2.88    --  -13.20  46.00 -60.00  202
  4  ω    -10.00  16.00   0.50    2.88    --  -13.20  37.00  60.00   52
  5  ω     34.00  76.00   0.50    2.88    --  -13.20  37.00  60.00   84
  6  ω    -18.00  17.00   0.50    2.88    --  -13.20  18.00   0.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1066446000
_diffrn_orient_matrix_UB_12      -0.0035680000
_diffrn_orient_matrix_UB_13      -0.0088514000
_diffrn_orient_matrix_UB_21      -0.0292516000
_diffrn_orient_matrix_UB_22      -0.0144723000
_diffrn_orient_matrix_UB_23      0.0346167000
_diffrn_orient_matrix_UB_31      -0.0186326000
_diffrn_orient_matrix_UB_32      0.0428741000
_diffrn_orient_matrix_UB_33      -0.0015535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3993
_reflns_number_total             8404
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.884
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.200
_refine_ls_extinction_coef       0.002(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   2.517
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3589
_refine_ls_R_factor_gt           0.2994
_refine_ls_restrained_S_all      2.517
_refine_ls_shift/su_max          1.150
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6882
_refine_ls_wR_factor_ref         0.7073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C39(H39A,H39B), C28(H28A,H28B), C27(H27A,H27B), C016(H01A,
 H01B), C01K(H01J,H01K), C01Q(H01M,H01N), C01V(H01R,H01S)
2.b Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C01D(H01D), C01L(H01L)
2.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C33(H33A,H33B,
 H33C), C00Z(H00A,H00B,H00C), C01H(H01C,H01E,H01F), C01I(H01G,H01H,H01I),
 C01S(H01O,H01P,H01Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.1660(12) 0.6490(5) 0.8988(4) 0.057(2) Uani 1 1 d . . . . .
F002 F 0.1023(15) 0.9307(5) 0.9024(4) 0.067(3) Uani 1 1 d . . . . .
F003 F 0.4675(13) 0.9722(5) 0.8309(4) 0.058(2) Uani 1 1 d . . . . .
N004 N -0.9765(14) 0.6932(6) 1.1293(5) 0.033(2) Uani 1 1 d . . . . .
C21 C 0.122(2) 0.7851(9) 0.9047(5) 0.045(4) Uani 1 1 d . . . . .
F006 F 0.5235(13) 0.6911(6) 0.8262(4) 0.061(2) Uani 1 1 d . . . . .
C31 C -0.6890(15) 0.6377(7) 1.0758(5) 0.022(2) Uani 1 1 d . . . . .
C29 C -0.7866(16) 0.7049(7) 1.0930(6) 0.028(3) Uani 1 1 d . . . . .
C36 C -0.5101(16) 0.6555(7) 1.0350(5) 0.024(2) Uani 1 1 d . . . . .
H36 H -0.449814 0.610985 1.021541 0.029 Uiso 1 1 calc R U . . .
C24 C 0.5058(16) 0.8329(8) 0.8283(6) 0.031(3) Uani 1 1 d . . . . .
C30 C -0.6840(17) 0.7881(7) 1.0734(6) 0.028(3) Uani 1 1 d . . . . .
C37 C -0.5055(16) 0.8017(8) 1.0333(6) 0.031(3) Uani 1 1 d . . . . .
H37 H -0.442673 0.856899 1.019072 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2032(19) 0.8714(8) 0.8843(6) 0.033(3) Uani 1 1 d . . . . .
C38 C -1.0827(17) 0.6089(7) 1.1463(9) 0.058(5) Uani 1 1 d . . . . .
H38A H -1.065974 0.579355 1.195299 0.070 Uiso 1 1 calc R U . . .
H38B H -1.235678 0.619653 1.138151 0.070 Uiso 1 1 calc R U . . .
C39 C -1.0181(17) 0.5510(9) 1.1127(7) 0.041(3) Uani 1 1 d . . . . .
H39A H -1.084332 0.568144 1.067732 0.049 Uiso 1 1 calc R U . . .
H39B H -1.069722 0.492970 1.138721 0.049 Uiso 1 1 calc R U . . .
C26 C -0.4128(18) 0.7378(9) 1.0125(6) 0.038(3) Uani 1 1 d . . . . .
C32 C -0.7758(17) 0.5480(7) 1.1040(6) 0.030(3) Uani 1 1 d . . . . .
F00I F 0.4752(12) 0.8099(5) 0.6718(4) 0.049(2) Uani 1 1 d . . . . .
C22 C 0.235(2) 0.7302(9) 0.8806(7) 0.045(3) Uani 1 1 d . . . . .
C25 C -0.2284(16) 0.7532(8) 0.9724(5) 0.029(3) Uani 1 1 d . . . . .
F12 F 0.8416(11) 0.8506(4) 0.6029(3) 0.0373(18) Uani 1 1 d . . . . .
C00M C -0.7659(19) 0.8546(8) 1.1044(6) 0.036(3) Uani 1 1 d . . . . .
C28 C -1.0844(18) 0.7606(8) 1.1410(9) 0.062(5) Uani 1 1 d . . . . .
H28A H -1.085824 0.749301 1.190303 0.074 Uiso 1 1 calc R U . . .
H28B H -1.232949 0.757964 1.127458 0.074 Uiso 1 1 calc R U . . .
C00O C -0.0692(16) 0.7667(8) 0.9399(6) 0.038(3) Uani 1 1 d . . . . .
C27 C -1.0129(19) 0.8473(9) 1.1095(7) 0.048(4) Uani 1 1 d . . . . .
H27A H -1.066847 0.882993 1.135684 0.057 Uiso 1 1 calc R U . . .
H27B H -1.072475 0.869922 1.063599 0.057 Uiso 1 1 calc R U . . .
C00Q C 0.394(2) 0.8922(8) 0.8474(6) 0.043(3) Uani 1 1 d . . . . .
C40 C -0.722(2) 0.4930(11) 1.0602(7) 0.059(5) Uani 1 1 d . . . . .
H40A H -0.789348 0.436810 1.079271 0.089 Uiso 1 1 calc R U . . .
H40B H -0.568031 0.485660 1.058997 0.089 Uiso 1 1 calc R U . . .
H40C H -0.772878 0.521149 1.014355 0.089 Uiso 1 1 calc R U . . .
C00S C 0.4203(19) 0.7513(9) 0.8443(6) 0.036(3) Uani 1 1 d . . . . .
F10 F 0.5300(13) 0.5273(5) 0.6676(4) 0.057(2) Uani 1 1 d . . . . .
F11 F 0.8936(11) 0.5668(5) 0.5999(4) 0.049(2) Uani 1 1 d . . . . .
C34 C -0.667(2) 0.8419(9) 1.1717(6) 0.050(4) Uani 1 1 d . . . . .
H34A H -0.767509 0.859633 1.200525 0.075 Uiso 1 1 calc R U . . .
H34B H -0.538552 0.876508 1.165519 0.075 Uiso 1 1 calc R U . . .
H34C H -0.632101 0.781378 1.193121 0.075 Uiso 1 1 calc R U . . .
C35 C -0.725(2) 0.9434(9) 1.0600(6) 0.046(4) Uani 1 1 d . . . . .
H35A H -0.790129 0.952467 1.016044 0.069 Uiso 1 1 calc R U . . .
H35B H -0.572157 0.952838 1.053952 0.069 Uiso 1 1 calc R U . . .
H35C H -0.785601 0.983550 1.080500 0.069 Uiso 1 1 calc R U . . .
C33 C -0.6804(17) 0.5050(8) 1.1744(6) 0.037(3) Uani 1 1 d . . . . .
H33A H -0.712195 0.539635 1.203180 0.055 Uiso 1 1 calc R U . . .
H33B H -0.526881 0.500181 1.170158 0.055 Uiso 1 1 calc R U . . .
H33C H -0.741696 0.447764 1.194689 0.055 Uiso 1 1 calc R U . . .
C00Y C 0.6983(17) 0.8536(10) 0.7909(7) 0.048(4) Uani 1 1 d . . . . .
C00Z C 1.7101(16) 0.5504(6) 0.4439(6) 0.031(3) Uani 1 1 d . . . . .
H00A H 1.770563 0.509274 0.424285 0.047 Uiso 1 1 calc R U . . .
H00B H 1.555762 0.544941 0.445882 0.047 Uiso 1 1 calc R U . . .
H00C H 1.764759 0.538835 0.489511 0.047 Uiso 1 1 calc R U . . .
N010 N 0.856(2) 0.8741(11) 0.7622(7) 0.083(5) Uani 1 1 d . . . . .
N11 N 1.9758(13) 0.8057(5) 0.3727(4) 0.023(2) Uani 1 1 d . . . . .
C20 C 0.6044(17) 0.6076(7) 0.6524(5) 0.030(3) Uani 1 1 d . . . . .
C015 C 1.7713(15) 0.6411(6) 0.4002(6) 0.023(2) Uani 1 1 d . . . . .
C016 C 2.0073(16) 0.6528(6) 0.3929(6) 0.029(3) Uani 1 1 d . . . . .
H01A H 2.068516 0.641019 0.438244 0.035 Uiso 1 1 calc R U . . .
H01B H 2.065756 0.610088 0.373815 0.035 Uiso 1 1 calc R U . . .
C017 C 0.7652(16) 0.7725(6) 0.6179(5) 0.020(2) Uani 1 1 d . . . . .
C018 C 0.7885(17) 0.6289(7) 0.6167(6) 0.027(3) Uani 1 1 d . . . . .
C019 C 1.4206(15) 0.7604(7) 0.4877(5) 0.022(2) Uani 1 1 d . . . . .
C01A C 1.2267(18) 0.7444(8) 0.5271(5) 0.030(3) Uani 1 1 d . . . . .
C01B C 0.5810(17) 0.7511(8) 0.6545(6) 0.031(3) Uani 1 1 d . . . . .
C01C C 1.7752(16) 0.9503(7) 0.3958(5) 0.026(2) Uani 1 1 d . . . . .
C01D C 1.5070(15) 0.6957(6) 0.4663(5) 0.020(2) Uani 1 1 d . . . . .
H01D H 1.440594 0.641163 0.479094 0.024 Uiso 1 1 calc R U . . .
C01E C 1.6916(14) 0.7106(7) 0.4259(5) 0.019(2) Uani 1 1 d . . . . .
N01F N 0.1484(17) 0.6281(10) 0.7388(6) 0.076(5) Uani 1 1 d . . . . .
C01G C 1.0670(18) 0.7306(7) 0.5598(5) 0.029(3) Uani 1 1 d . . . . .
C01H C 1.6764(16) 0.6599(7) 0.3281(6) 0.028(3) Uani 1 1 d . . . . .
H01C H 1.733565 0.618857 0.307772 0.042 Uiso 1 1 calc R U . . .
H01E H 1.714347 0.718131 0.299779 0.042 Uiso 1 1 calc R U . . .
H01F H 1.522171 0.654406 0.331565 0.042 Uiso 1 1 calc R U . . .
C01I C 1.674(2) 0.9945(8) 0.3256(6) 0.043(3) Uani 1 1 d . . . . .
H01G H 1.757369 1.045198 0.300802 0.065 Uiso 1 1 calc R U . . .
H01H H 1.529154 1.011568 0.331682 0.065 Uiso 1 1 calc R U . . .
H01I H 1.673082 0.954414 0.300137 0.065 Uiso 1 1 calc R U . . .
C01K C 2.0753(17) 0.7400(7) 0.3492(5) 0.029(3) Uani 1 1 d . . . . .
H01J H 2.231039 0.744780 0.350537 0.035 Uiso 1 1 calc R U . . .
H01K H 2.034328 0.749124 0.301997 0.035 Uiso 1 1 calc R U . . .
C01L C 1.5083(15) 0.8422(6) 0.4653(5) 0.021(2) Uani 1 1 d . . . . .
H01L H 1.443429 0.886600 0.477881 0.026 Uiso 1 1 calc R U . . .
C01N C 0.4979(17) 0.6683(9) 0.6726(5) 0.036(3) Uani 1 1 d . . . . .
C01O C 0.298(2) 0.6441(10) 0.7091(6) 0.055(4) Uani 1 1 d . . . . .
C01P C 1.7849(14) 0.7913(6) 0.4074(5) 0.016(2) Uani 1 1 d . . . . .
C01Q C 2.0150(16) 0.9448(6) 0.3893(6) 0.025(2) Uani 1 1 d . . . . .
H01M H 2.073855 1.003007 0.368269 0.030 Uiso 1 1 calc R U . . .
H01N H 2.076981 0.920101 0.434677 0.030 Uiso 1 1 calc R U . . .
C01S C 1.7308(18) 1.0062(6) 0.4388(6) 0.033(3) Uani 1 1 d . . . . .
H01O H 1.795794 1.062562 0.417732 0.050 Uiso 1 1 calc R U . . .
H01P H 1.790134 0.979401 0.483802 0.050 Uiso 1 1 calc R U . . .
H01Q H 1.577694 1.012889 0.442756 0.050 Uiso 1 1 calc R U . . .
C01T C 1.6887(16) 0.8599(7) 0.4251(5) 0.024(2) Uani 1 1 d . . . . .
C01U C 0.8794(13) 0.7051(6) 0.6017(5) 0.013(2) Uani 1 1 d . . . . .
C01V C 2.0748(17) 0.8898(7) 0.3468(5) 0.025(3) Uani 1 1 d . . . . .
H01R H 2.029897 0.918645 0.299743 0.030 Uiso 1 1 calc R U . . .
H01S H 2.230361 0.883114 0.346704 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C22 1.342(14) . ?
F002 C23 1.324(13) . ?
F003 C00Q 1.337(14) . ?
N004 C29 1.395(14) . ?
N004 C38 1.483(14) . ?
N004 C28 1.395(14) . ?
C21 C23 1.443(18) . ?
C21 C22 1.37(2) . ?
C21 C00O 1.392(17) . ?
F006 C00S 1.345(14) . ?
C31 C29 1.416(15) . ?
C31 C36 1.384(14) . ?
C31 C32 1.508(15) . ?
C29 C30 1.453(15) . ?
C36 H36 0.9500 . ?
C36 C26 1.425(16) . ?
C24 C00Q 1.370(18) . ?
C24 C00S 1.389(17) . ?
C24 C00Y 1.422(15) . ?
C30 C37 1.375(16) . ?
C30 C00M 1.540(16) . ?
C37 H37 0.9500 . ?
C37 C26 1.396(16) . ?
C23 C00Q 1.408(18) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.422(18) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C32 1.544(15) . ?
C26 C25 1.406(16) . ?
C32 C40 1.530(17) . ?
C32 C33 1.543(15) . ?
F00I C01B 1.324(13) . ?
C22 C00S 1.375(17) . ?
C25 C00O 1.191(15) . ?
F12 C017 1.317(11) . ?
C00M C27 1.567(17) . ?
C00M C34 1.501(15) . ?
C00M C35 1.479(18) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.438(18) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
F10 C20 1.346(12) . ?
F11 C018 1.363(12) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C00Y N010 1.156(17) . ?
C00Z H00A 0.9800 . ?
C00Z H00B 0.9800 . ?
C00Z H00C 0.9800 . ?
C00Z C015 1.526(13) . ?
N11 C01K 1.472(14) . ?
N11 C01P 1.384(11) . ?
N11 C01V 1.458(13) . ?
C20 C018 1.361(15) . ?
C20 C01N 1.385(17) . ?
C015 C016 1.505(13) . ?
C015 C01E 1.507(14) . ?
C015 C01H 1.569(15) . ?
C016 H01A 0.9900 . ?
C016 H01B 0.9900 . ?
C016 C01K 1.494(14) . ?
C017 C01B 1.371(14) . ?
C017 C01U 1.457(12) . ?
C018 C01U 1.326(13) . ?
C019 C01A 1.447(14) . ?
C019 C01D 1.399(14) . ?
C019 C01L 1.393(13) . ?
C01A C01G 1.196(15) . ?
C01B C01N 1.398(17) . ?
C01C C01I 1.557(15) . ?
C01C C01Q 1.527(14) . ?
C01C C01S 1.517(15) . ?
C01C C01T 1.519(14) . ?
C01D H01D 0.9500 . ?
C01D C01E 1.410(13) . ?
C01E C01P 1.393(12) . ?
N01F C01O 1.113(16) . ?
C01G C01U 1.448(14) . ?
C01H H01C 0.9800 . ?
C01H H01E 0.9800 . ?
C01H H01F 0.9800 . ?
C01I H01G 0.9800 . ?
C01I H01H 0.9800 . ?
C01I H01I 0.9800 . ?
C01K H01J 0.9900 . ?
C01K H01K 0.9900 . ?
C01L H01L 0.9500 . ?
C01L C01T 1.386(14) . ?
C01N C01O 1.456(16) . ?
C01P C01T 1.438(14) . ?
C01Q H01M 0.9900 . ?
C01Q H01N 0.9900 . ?
C01Q C01V 1.514(14) . ?
C01S H01O 0.9800 . ?
C01S H01P 0.9800 . ?
C01S H01Q 0.9800 . ?
C01V H01R 0.9900 . ?
C01V H01S 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
C29 N004 C38 117.9(9) . . ?
C28 N004 C29 122.5(10) . . ?
C28 N004 C38 118.8(9) . . ?
C22 C21 C23 114.8(12) . . ?
C22 C21 C00O 125.8(13) . . ?
C00O C21 C23 119.1(14) . . ?
C29 C31 C32 119.9(10) . . ?
C36 C31 C29 118.9(10) . . ?
C36 C31 C32 121.2(10) . . ?
N004 C29 C31 122.0(10) . . ?
N004 C29 C30 118.9(10) . . ?
C31 C29 C30 119.1(10) . . ?
C31 C36 H36 118.7 . . ?
C31 C36 C26 122.6(10) . . ?
C26 C36 H36 118.7 . . ?
C00Q C24 C00S 117.6(11) . . ?
C00Q C24 C00Y 122.1(12) . . ?
C00S C24 C00Y 120.3(12) . . ?
C29 C30 C00M 118.4(10) . . ?
C37 C30 C29 119.0(11) . . ?
C37 C30 C00M 122.3(10) . . ?
C30 C37 H37 118.6 . . ?
C30 C37 C26 122.8(11) . . ?
C26 C37 H37 118.6 . . ?
F002 C23 C21 120.0(12) . . ?
F002 C23 C00Q 119.7(12) . . ?
C00Q C23 C21 120.2(12) . . ?
N004 C38 H38A 107.5 . . ?
N004 C38 H38B 107.5 . . ?
H38A C38 H38B 107.0 . . ?
C39 C38 N004 119.3(11) . . ?
C39 C38 H38A 107.5 . . ?
C39 C38 H38B 107.5 . . ?
C38 C39 H39A 109.0 . . ?
C38 C39 H39B 109.0 . . ?
C38 C39 C32 113.0(10) . . ?
H39A C39 H39B 107.8 . . ?
C32 C39 H39A 109.0 . . ?
C32 C39 H39B 109.0 . . ?
C37 C26 C36 117.2(11) . . ?
C37 C26 C25 121.5(12) . . ?
C25 C26 C36 121.3(12) . . ?
C31 C32 C39 109.8(9) . . ?
C31 C32 C40 113.0(11) . . ?
C31 C32 C33 108.4(9) . . ?
C40 C32 C39 109.6(10) . . ?
C40 C32 C33 108.2(10) . . ?
C33 C32 C39 107.8(10) . . ?
F001 C22 C21 116.9(12) . . ?
F001 C22 C00S 118.6(14) . . ?
C21 C22 C00S 124.2(13) . . ?
C00O C25 C26 178.1(12) . . ?
C30 C00M C27 107.9(10) . . ?
C34 C00M C30 111.2(10) . . ?
C34 C00M C27 112.0(11) . . ?
C35 C00M C30 112.1(10) . . ?
C35 C00M C27 104.6(10) . . ?
C35 C00M C34 108.9(11) . . ?
N004 C28 H28A 107.3 . . ?
N004 C28 H28B 107.3 . . ?
N004 C28 C27 120.1(11) . . ?
H28A C28 H28B 106.9 . . ?
C27 C28 H28A 107.3 . . ?
C27 C28 H28B 107.3 . . ?
C25 C00O C21 176.3(13) . . ?
C00M C27 H27A 109.1 . . ?
C00M C27 H27B 109.1 . . ?
C28 C27 C00M 112.7(11) . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
F003 C00Q C24 119.4(12) . . ?
F003 C00Q C23 118.7(13) . . ?
C24 C00Q C23 121.9(11) . . ?
C32 C40 H40A 109.5 . . ?
C32 C40 H40B 109.5 . . ?
C32 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
F006 C00S C24 119.7(11) . . ?
F006 C00S C22 119.3(13) . . ?
C22 C00S C24 120.9(13) . . ?
C00M C34 H34A 109.5 . . ?
C00M C34 H34B 109.5 . . ?
C00M C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C00M C35 H35A 109.5 . . ?
C00M C35 H35B 109.5 . . ?
C00M C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N010 C00Y C24 176.2(17) . . ?
H00A C00Z H00B 109.5 . . ?
H00A C00Z H00C 109.5 . . ?
H00B C00Z H00C 109.5 . . ?
C015 C00Z H00A 109.5 . . ?
C015 C00Z H00B 109.5 . . ?
C015 C00Z H00C 109.5 . . ?
C01P N11 C01K 121.7(8) . . ?
C01P N11 C01V 123.0(9) . . ?
C01V N11 C01K 114.5(8) . . ?
F10 C20 C018 119.0(11) . . ?
F10 C20 C01N 121.3(10) . . ?
C018 C20 C01N 119.8(10) . . ?
C00Z C015 C01H 109.0(8) . . ?
C016 C015 C00Z 112.1(9) . . ?
C016 C015 C01E 105.9(8) . . ?
C016 C015 C01H 108.1(9) . . ?
C01E C015 C00Z 114.8(9) . . ?
C01E C015 C01H 106.6(8) . . ?
C015 C016 H01A 108.7 . . ?
C015 C016 H01B 108.7 . . ?
H01A C016 H01B 107.6 . . ?
C01K C016 C015 114.2(9) . . ?
C01K C016 H01A 108.7 . . ?
C01K C016 H01B 108.7 . . ?
F12 C017 C01B 119.7(9) . . ?
F12 C017 C01U 122.1(9) . . ?
C01B C017 C01U 118.0(9) . . ?
C20 C018 F11 118.2(10) . . ?
C01U C018 F11 118.0(10) . . ?
C01U C018 C20 123.6(10) . . ?
C01D C019 C01A 119.6(9) . . ?
C01L C019 C01A 120.1(10) . . ?
C01L C019 C01D 120.0(9) . . ?
C01G C01A C019 179.5(15) . . ?
F00I C01B C017 120.0(10) . . ?
F00I C01B C01N 118.7(10) . . ?
C017 C01B C01N 121.3(11) . . ?
C01Q C01C C01I 110.7(9) . . ?
C01S C01C C01I 107.6(10) . . ?
C01S C01C C01Q 107.2(9) . . ?
C01S C01C C01T 114.1(9) . . ?
C01T C01C C01I 109.0(8) . . ?
C01T C01C C01Q 108.2(9) . . ?
C019 C01D H01D 119.7 . . ?
C019 C01D C01E 120.6(9) . . ?
C01E C01D H01D 119.7 . . ?
C01D C01E C015 118.9(8) . . ?
C01P C01E C015 122.5(9) . . ?
C01P C01E C01D 118.5(9) . . ?
C01A C01G C01U 174.4(12) . . ?
C015 C01H H01C 109.5 . . ?
C015 C01H H01E 109.5 . . ?
C015 C01H H01F 109.5 . . ?
H01C C01H H01E 109.5 . . ?
H01C C01H H01F 109.5 . . ?
H01E C01H H01F 109.5 . . ?
C01C C01I H01G 109.5 . . ?
C01C C01I H01H 109.5 . . ?
C01C C01I H01I 109.5 . . ?
H01G C01I H01H 109.5 . . ?
H01G C01I H01I 109.5 . . ?
H01H C01I H01I 109.5 . . ?
N11 C01K C016 110.2(9) . . ?
N11 C01K H01J 109.6 . . ?
N11 C01K H01K 109.6 . . ?
C016 C01K H01J 109.6 . . ?
C016 C01K H01K 109.6 . . ?
H01J C01K H01K 108.1 . . ?
C019 C01L H01L 119.5 . . ?
C01T C01L C019 121.1(10) . . ?
C01T C01L H01L 119.5 . . ?
C20 C01N C01B 118.7(10) . . ?
C20 C01N C01O 118.3(12) . . ?
C01B C01N C01O 122.8(13) . . ?
N01F C01O C01N 176.5(18) . . ?
N11 C01P C01E 119.7(9) . . ?
N11 C01P C01T 119.1(8) . . ?
C01E C01P C01T 121.1(9) . . ?
C01C C01Q H01M 109.4 . . ?
C01C C01Q H01N 109.4 . . ?
H01M C01Q H01N 108.0 . . ?
C01V C01Q C01C 111.0(8) . . ?
C01V C01Q H01M 109.4 . . ?
C01V C01Q H01N 109.4 . . ?
C01C C01S H01O 109.5 . . ?
C01C C01S H01P 109.5 . . ?
C01C C01S H01Q 109.5 . . ?
H01O C01S H01P 109.5 . . ?
H01O C01S H01Q 109.5 . . ?
H01P C01S H01Q 109.5 . . ?
C01L C01T C01C 121.4(10) . . ?
C01L C01T C01P 118.3(9) . . ?
C01P C01T C01C 120.1(9) . . ?
C018 C01U C017 118.3(9) . . ?
C018 C01U C01G 124.1(9) . . ?
C01G C01U C017 116.7(9) . . ?
N11 C01V C01Q 111.2(9) . . ?
N11 C01V H01R 109.4 . . ?
N11 C01V H01S 109.4 . . ?
C01Q C01V H01R 109.4 . . ?
C01Q C01V H01S 109.4 . . ?
H01R C01V H01S 108.0 . . ?

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
F001 C22 C00S F006 2.3(17) . . . . ?
F001 C22 C00S C24 -175.5(10) . . . . ?
F002 C23 C00Q F003 -0.7(16) . . . . ?
F002 C23 C00Q C24 179.2(10) . . . . ?
N004 C29 C30 C37 -175.1(10) . . . . ?
N004 C29 C30 C00M 11.2(15) . . . . ?
N004 C38 C39 C32 41.3(18) . . . . ?
N004 C28 C27 C00M -37(2) . . . . ?
C21 C23 C00Q F003 -178.3(9) . . . . ?
C21 C23 C00Q C24 1.5(17) . . . . ?
C21 C22 C00S F006 176.5(11) . . . . ?
C21 C22 C00S C24 -1.3(19) . . . . ?
C31 C29 C30 C37 6.0(16) . . . . ?
C31 C29 C30 C00M -167.7(9) . . . . ?
C31 C36 C26 C37 0.0(15) . . . . ?
C31 C36 C26 C25 178.6(9) . . . . ?
C29 N004 C38 C39 -14.6(19) . . . . ?
C29 N004 C28 C27 6(2) . . . . ?
C29 C31 C36 C26 3.5(15) . . . . ?
C29 C31 C32 C39 32.8(13) . . . . ?
C29 C31 C32 C40 155.5(9) . . . . ?
C29 C31 C32 C33 -84.7(11) . . . . ?
C29 C30 C37 C26 -2.6(17) . . . . ?
C29 C30 C00M C27 -38.5(14) . . . . ?
C29 C30 C00M C34 84.8(13) . . . . ?
C29 C30 C00M C35 -153.1(10) . . . . ?
C36 C31 C29 N004 174.8(9) . . . . ?
C36 C31 C29 C30 -6.4(15) . . . . ?
C36 C31 C32 C39 -149.5(10) . . . . ?
C36 C31 C32 C40 -26.9(14) . . . . ?
C36 C31 C32 C33 93.0(12) . . . . ?
C30 C37 C26 C36 -0.4(16) . . . . ?
C30 C37 C26 C25 -179.0(10) . . . . ?
C30 C00M C27 C28 50.1(15) . . . . ?
C37 C30 C00M C27 148.0(11) . . . . ?
C37 C30 C00M C34 -88.7(14) . . . . ?
C37 C30 C00M C35 33.4(15) . . . . ?
C23 C21 C22 F001 179.3(9) . . . . ?
C23 C21 C22 C00S 5.1(18) . . . . ?
C38 N004 C29 C31 -3.7(16) . . . . ?
C38 N004 C29 C30 177.5(11) . . . . ?
C38 N004 C28 C27 -163.5(13) . . . . ?
C38 C39 C32 C31 -48.5(15) . . . . ?
C38 C39 C32 C40 -173.2(12) . . . . ?
C38 C39 C32 C33 69.3(14) . . . . ?
C32 C31 C29 N004 -7.5(15) . . . . ?
C32 C31 C29 C30 171.3(9) . . . . ?
C32 C31 C36 C26 -174.2(9) . . . . ?
F00I C01B C01N C20 177.7(10) . . . . ?
F00I C01B C01N C01O 0.8(17) . . . . ?
C22 C21 C23 F002 177.3(10) . . . . ?
C22 C21 C23 C00Q -5.1(16) . . . . ?
F12 C017 C01B F00I 3.3(16) . . . . ?
F12 C017 C01B C01N -178.4(10) . . . . ?
F12 C017 C01U C018 -178.0(10) . . . . ?
F12 C017 C01U C01G -8.7(14) . . . . ?
C00M C30 C37 C26 170.8(10) . . . . ?
C28 N004 C29 C31 -173.7(12) . . . . ?
C28 N004 C29 C30 7.5(17) . . . . ?
C28 N004 C38 C39 155.9(14) . . . . ?
C00O C21 C23 F002 3.7(16) . . . . ?
C00O C21 C23 C00Q -178.6(10) . . . . ?
C00O C21 C22 F001 -7.6(18) . . . . ?
C00O C21 C22 C00S 178.1(11) . . . . ?
C00Q C24 C00S F006 179.5(10) . . . . ?
C00Q C24 C00S C22 -2.7(17) . . . . ?
C00S C24 C00Q F003 -177.7(10) . . . . ?
C00S C24 C00Q C23 2.4(17) . . . . ?
F10 C20 C018 F11 -2.2(16) . . . . ?
F10 C20 C018 C01U -177.0(10) . . . . ?
F10 C20 C01N C01B -179.0(10) . . . . ?
F10 C20 C01N C01O -1.9(16) . . . . ?
F11 C018 C01U C017 178.3(9) . . . . ?
F11 C018 C01U C01G 9.8(16) . . . . ?
C34 C00M C27 C28 -72.7(15) . . . . ?
C35 C00M C27 C28 169.5(12) . . . . ?
C00Y C24 C00Q F003 -0.3(17) . . . . ?
C00Y C24 C00Q C23 179.9(11) . . . . ?
C00Y C24 C00S F006 2.0(17) . . . . ?
C00Y C24 C00S C22 179.8(11) . . . . ?
C00Z C015 C016 C01K 178.6(9) . . . . ?
C00Z C015 C01E C01D -26.5(13) . . . . ?
C00Z C015 C01E C01P 158.1(9) . . . . ?
N11 C01P C01T C01C 10.5(14) . . . . ?
N11 C01P C01T C01L -173.9(9) . . . . ?
C20 C018 C01U C017 -6.9(17) . . . . ?
C20 C018 C01U C01G -175.4(10) . . . . ?
C015 C016 C01K N11 53.5(12) . . . . ?
C015 C01E C01P N11 -10.1(15) . . . . ?
C015 C01E C01P C01T 171.4(9) . . . . ?
C016 C015 C01E C01D -150.8(9) . . . . ?
C016 C015 C01E C01P 33.8(13) . . . . ?
C017 C01B C01N C20 -0.6(17) . . . . ?
C017 C01B C01N C01O -177.5(11) . . . . ?
C018 C20 C01N C01B 1.3(16) . . . . ?
C018 C20 C01N C01O 178.4(11) . . . . ?
C019 C01D C01E C015 -176.1(9) . . . . ?
C019 C01D C01E C01P -0.5(14) . . . . ?
C019 C01L C01T C01C 174.9(9) . . . . ?
C019 C01L C01T C01P -0.6(15) . . . . ?
C01A C019 C01D C01E 177.8(9) . . . . ?
C01A C019 C01L C01T -177.2(9) . . . . ?
C01B C017 C01U C018 7.3(15) . . . . ?
C01B C017 C01U C01G 176.6(9) . . . . ?
C01C C01Q C01V N11 -54.1(11) . . . . ?
C01D C019 C01L C01T -3.8(15) . . . . ?
C01D C01E C01P N11 174.4(8) . . . . ?
C01D C01E C01P C01T -4.0(14) . . . . ?
C01E C015 C016 C01K -55.5(12) . . . . ?
C01E C01P C01T C01C -171.0(9) . . . . ?
C01E C01P C01T C01L 4.6(15) . . . . ?
C01H C015 C016 C01K 58.4(12) . . . . ?
C01H C015 C01E C01D 94.2(10) . . . . ?
C01H C015 C01E C01P -81.2(11) . . . . ?
C01I C01C C01Q C01V -62.9(12) . . . . ?
C01I C01C C01T C01L -90.3(12) . . . . ?
C01I C01C C01T C01P 85.1(12) . . . . ?
C01K N11 C01P C01E 5.6(14) . . . . ?
C01K N11 C01P C01T -175.9(8) . . . . ?
C01K N11 C01V C01Q -161.3(8) . . . . ?
C01L C019 C01D C01E 4.4(14) . . . . ?
C01N C20 C018 F11 177.5(9) . . . . ?
C01N C20 C018 C01U 2.7(18) . . . . ?
C01P N11 C01K C016 -26.6(12) . . . . ?
C01P N11 C01V C01Q 28.7(13) . . . . ?
C01Q C01C C01T C01L 149.3(9) . . . . ?
C01Q C01C C01T C01P -35.3(13) . . . . ?
C01S C01C C01Q C01V -180.0(9) . . . . ?
C01S C01C C01T C01L 30.0(14) . . . . ?
C01S C01C C01T C01P -154.6(10) . . . . ?
C01T C01C C01Q C01V 56.5(11) . . . . ?
C01U C017 C01B F00I 178.1(9) . . . . ?
C01U C017 C01B C01N -3.6(16) . . . . ?
C01V N11 C01K C016 163.3(8) . . . . ?
C01V N11 C01P C01E 174.9(9) . . . . ?
C01V N11 C01P C01T -6.7(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.750
_chemical_properties_physical    
Oxygen-sensitive,Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
