#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131873.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131873
loop_
_publ_author_name
'Cheng, Xiuliang'
'He, Yuhang'
'Song, Silin'
'Lin, Yu-Mei'
'Gong, Lei'
_publ_section_title
;
 A transition metal- and photosensitizer-free approach for site-selective
 (hetero)arylation of polychlorinated heteroarenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02968A
_journal_year                    2023
_chemical_formula_moiety         'C20 H12 Cl F3 N2'
_chemical_formula_sum            'C20 H12 Cl F3 N2'
_chemical_formula_weight         372.76
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-16 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   31.8395(3)
_cell_length_b                   31.8395(3)
_cell_length_c                   8.58300(10)
_cell_measurement_reflns_used    31048
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4260
_cell_measurement_theta_min      4.7600
_cell_volume                     7535.33(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -72.00   1.00    1.00    --  -40.50-161.00 130.00   30
  2  ω    -86.00  -6.00   1.00    1.00    --  -40.50 125.00 -90.00   80
  3  ω   -117.00  -9.00   1.00    1.00    --  -40.50 -19.00   0.00  108
  4  ω    -55.00  32.00   1.00    1.00    --  -40.50  37.00-180.00   87
  5  ω     55.00  92.00   1.00    1.00    --   42.79-125.00-180.00   37
  6  ω     57.00 112.00   1.00    1.00    --  111.00-125.00   0.00   55
  7  ω    100.00 176.00   1.00    1.00    --  111.00  45.00-150.00   76
  8  ω    110.00 141.00   1.00    1.00    --  111.00  77.00 -60.00   31
  9  ω     78.00 107.00   1.00    1.00    --  111.00 -94.00  90.00   29
 10  ω     82.00 107.00   1.00    1.00    --  111.00 -94.00-120.00   25
 11  ω     59.00  93.00   1.00    1.00    --  111.00 -61.00   0.00   34
 12  ω     94.00 136.00   1.00    1.00    --  111.00 -61.00   0.00   42
 13  ω     83.00 178.00   1.00    1.00    --  111.00  61.00  90.00   95
 14  ω    104.00 178.00   1.00    1.00    --  111.00  77.00 150.00   74
 15  ω    130.00 157.00   1.00    1.00    --  111.00  77.00  30.00   27
 16  ω     31.00  67.00   1.00    1.00    --  111.00 -94.00-120.00   36
 17  ω     86.00 112.00   1.00    1.00    --  111.00-125.00-180.00   26
 18  ω     40.00 110.00   1.00    1.00    --  111.00 -45.00  90.00   70
 19  ω    122.00 167.00   1.00    1.00    --  111.00 125.00 120.00   45
 20  ω     73.00 107.00   1.00    1.00    --  111.00 -94.00-180.00   34
 21  ω     57.00 103.00   1.00    1.00    --  111.00 -94.00  30.00   46
 22  ω     98.00 165.00   1.00    1.00    --  111.00 125.00  30.00   67
 23  ω     21.00  57.00   1.00    1.00    --   43.04-117.00 -78.00   36
 24  ω    124.00 157.00   1.00    1.00    --  111.00 125.00 -90.00   33
 25  ω     54.00  80.00   1.00    1.00    --  111.00-117.00 -78.00   26
 26  ω     36.00  68.00   1.00    1.00    --  111.00 -30.00 -90.00   32
 27  ω    110.00 135.00   1.00    1.00    --  111.00 -30.00 -90.00   25
 28  ω     81.00 107.00   1.00    1.00    --  111.00 -94.00 120.00   26
 29  ω     98.00 123.00   1.00    1.00    --  111.00-138.00 -17.85   25
 30  ω     64.00  90.00   1.00    1.00    --  111.00-138.00 -17.85   26
 31  ω    -54.00  15.00   1.00    1.00    --  -40.50  37.00 120.00   69
 32  ω     56.00 104.00   1.00    1.00    --   43.04  57.00  60.00   48
 33  ω     16.00  97.00   1.00    1.00    --   43.04  57.00 150.00   81
 34  ω     13.00  42.00   1.00    1.00    --   43.04  79.00  -0.66   29
 35  ω     87.00 113.00   1.00    1.00    --   43.04  57.00 -60.00   26
 36  ω     21.00  92.00   1.00    1.00    --   43.04  37.00-120.00   71
 37  ω     16.00  52.00   1.00    1.00    --   43.04  57.00  60.00   36
 38  ω     16.00  80.00   1.00    1.00    --   43.04  57.00 -60.00   64
 39  ω     10.00  42.00   1.00    1.00    --   43.04  82.00 -62.06   32
 40  ω     11.00  42.00   1.00    1.00    --   43.04  81.00 177.34   31
 41  ω     12.00  41.00   1.00    1.00    --   43.04  79.00  83.38   29
 42  ω     48.00  78.00   1.00    1.00    --   43.04-162.00 131.00   30
 43  ω     12.00  42.00   1.00    1.00    --   43.04  82.00-146.80   30
 44  ω     86.00 112.00   1.00    1.00    --  111.00  48.00 178.05   26
 45  ω     84.00 110.00   1.00    1.00    --  111.00  58.00  43.09   26
 46  ω     82.00 107.00   1.00    1.00    --  111.00  66.00  61.55   25
 47  ω    121.00 147.00   1.00    1.00    --  111.00  64.00 -14.46   26
 48  ω     83.00 108.00   1.00    1.00    --  111.00  64.00 -14.46   25
 49  ω     82.00 108.00   1.00    1.00    --  111.00  66.00  96.11   26
 50  ω     84.00 110.00   1.00    1.00    --  111.00  59.00 -18.14   26
 51  ω    153.00 178.00   1.00    1.00    --  111.00  48.00 -61.42   25
 52  ω     83.00 109.00   1.00    1.00    --  111.00  61.00 -30.00   26
 53  ω     85.00 128.00   1.00    1.00    --  111.00  55.00 141.47   43
 54  ω     83.00 109.00   1.00    1.00    --  111.00  62.00-174.04   26
 55  ω     83.00 128.00   1.00    1.00    --  111.00  61.00 150.00   45
 56  ω     87.00 113.00   1.00    1.00    --  111.00  45.00 -30.00   26
 57  ω     83.00 108.00   1.00    1.00    --  111.00  61.00  30.00   25
 58  ω     83.00 108.00   1.00    1.00    --  111.00  61.00-120.00   25
 59  ω     83.00 159.00   1.00    1.00    --  111.00  61.00   0.00   76
 60  ω     83.00 109.00   1.00    1.00    --  111.00  61.00 -60.00   26
 61  ω     86.00 140.00   1.00    1.00    --  111.00  48.00 -61.42   54
 62  ω     85.00 162.00   1.00    1.00    --  111.00  54.00 -94.92   77
 63  ω     85.00 121.00   1.00    1.00    --  111.00  56.00  58.25   36
 64  ω    150.00 177.00   1.00    1.00    --  111.00  65.00-140.52   27
 65  ω     85.00 158.00   1.00    1.00    --  111.00  55.00  21.75   73
 66  ω     83.00 109.00   1.00    1.00    --  111.00  61.00-150.00   26
 67  ω     83.00 109.00   1.00    1.00    --  111.00  61.00 120.00   26
 68  ω     83.00 109.00   1.00    1.00    --  111.00  65.00-140.52   26
 69  ω     83.00 109.00   1.00    1.00    --  111.00  61.00 -90.00   26
 70  ω     83.00 108.00   1.00    1.00    --  111.00  61.00-180.00   25
 71  ω     83.00 108.00   1.00    1.00    --  111.00  64.00-158.54   25
 72  ω     85.00 111.00   1.00    1.00    --  111.00  53.00  85.64   26
 73  ω     86.00 112.00   1.00    1.00    --  111.00  58.00 112.81   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0456402000
_diffrn_orient_matrix_UB_12      0.0029229000
_diffrn_orient_matrix_UB_13      -0.0400281000
_diffrn_orient_matrix_UB_21      0.0311333000
_diffrn_orient_matrix_UB_22      0.0555686000
_diffrn_orient_matrix_UB_23      -0.0132225000
_diffrn_orient_matrix_UB_31      0.0081544000
_diffrn_orient_matrix_UB_32      -0.0048524000
_diffrn_orient_matrix_UB_33      -0.1744880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            46317
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.470
_diffrn_reflns_theta_min         2.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       plate
_exptl_crystal_F_000             3420
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_extinction_coef       0.00010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6667
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0647P)²+13.8711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                6590
_reflns_number_total             6667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02968a2.cif
_cod_data_source_block           exp_19124_auto
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H24 Cl2 F6 N4'
_cod_original_formula_weight         745.53
_cod_original_formula_moiety         '2(C20 H12 Cl F3 N2)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        7535.33(17)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               7131873
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'C H  N Cl F'
_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.
;
_shelx_estimated_absorpt_t_max   0.452
_shelx_estimated_absorpt_t_min   0.254
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N008(H008), N00A(H00A), C00F(H00F), C00I(H00I), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00V(H00V), C00Y(H00Y), C00Z(H00Z), C010(H010), C012(H012),
 C013(H013), C015(H015), C016(H016), C017(H017), C018(H018), C019(H019),
 C01A(H01A), C01B(H01B), C01C(H01C), C01E(H01E), C01F(H01F), C01G(H01G)
;
_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 2.139
_oxdiff_exptl_absorpt_empirical_full_min 0.605
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
Cl1 Cl 0.54260(3) 0.93126(4) 0.98705(11) 0.0367(2) Uani 1 1 d . . . . .
Cl Cl 0.60224(3) 0.81030(4) 0.48485(11) 0.0387(2) Uani 1 1 d . . . . .
F003 F 0.63267(10) 0.89854(8) -0.0493(4) 0.0455(6) Uani 1 1 d . . . . .
F004 F 0.58261(10) 0.84624(9) -0.2112(3) 0.0454(6) Uani 1 1 d . . . . .
F005 F 0.58383(12) 0.96776(10) 0.3159(3) 0.0535(7) Uani 1 1 d . . . . .
F006 F 0.65154(11) 0.85115(11) -0.1698(4) 0.0541(8) Uani 1 1 d . . . . .
F007 F 0.57884(16) 0.89959(14) 0.3040(4) 0.0746(11) Uani 1 1 d . . . . .
N008 N 0.36559(11) 0.83358(11) 0.9798(4) 0.0269(6) Uani 1 1 d . . . . .
H008 H 0.336494 0.828738 1.001634 0.032 Uiso 1 1 calc R U . . .
N009 N 0.53545(11) 0.73599(11) 0.1042(4) 0.0276(6) Uani 1 1 d . . . . .
N00A N 0.46850(12) 0.64215(12) 0.4941(4) 0.0309(7) Uani 1 1 d . . . . .
H00A H 0.454584 0.611223 0.518789 0.037 Uiso 1 1 calc R U . . .
N N 0.46589(11) 0.87480(11) 0.6010(4) 0.0259(6) Uani 1 1 d . . . . .
C00C C 0.38494(14) 0.89938(14) 0.7891(4) 0.0280(7) Uani 1 1 d . . . . .
C00D C 0.47775(13) 0.88520(13) 0.7529(4) 0.0251(7) Uani 1 1 d . . . . .
C00E C 0.39667(13) 0.86606(13) 0.8733(4) 0.0266(7) Uani 1 1 d . . . . .
C00F C 0.55749(13) 0.76942(13) -0.0057(4) 0.0265(7) Uani 1 1 d . . . . .
H00F H 0.548799 0.760459 -0.111411 0.032 Uiso 1 1 calc R U . . .
C00G C 0.50344(13) 0.66486(13) 0.3851(4) 0.0280(7) Uani 1 1 d . . . . .
F00H F 0.63111(12) 0.9558(3) 0.4554(4) 0.132(3) Uani 1 1 d . . . . .
C00I C 0.50117(14) 0.89053(14) 0.4946(4) 0.0300(8) Uani 1 1 d . . . . .
H00I H 0.492260 0.883024 0.388285 0.036 Uiso 1 1 calc R U . . .
C00J C 0.54680(13) 0.74819(13) 0.2554(5) 0.0268(7) Uani 1 1 d . . . . .
C00K C 0.48774(14) 0.72026(14) 0.4895(4) 0.0298(8) Uani 1 1 d . . . . .
C00L C 0.43296(13) 0.82717(13) 0.9810(4) 0.0276(7) Uani 1 1 d . . . . .
C00M C 0.51640(13) 0.71294(13) 0.3751(5) 0.0280(7) Uani 1 1 d . . . . .
C00N C 0.38676(13) 0.80953(13) 1.0480(4) 0.0271(7) Uani 1 1 d . . . . .
C00O C 0.59272(13) 0.81696(12) 0.0277(5) 0.0275(7) Uani 1 1 d . . . . .
C00P C 0.45834(14) 0.67557(14) 0.5602(5) 0.0305(8) Uani 1 1 d . . . . .
C00Q C 0.32595(16) 0.91762(17) 0.6806(5) 0.0374(9) Uani 1 1 d . . . . .
H00Q H 0.293081 0.908645 0.662254 0.045 Uiso 1 1 calc R U . . .
C00R C 0.52295(14) 0.63781(14) 0.2981(5) 0.0305(8) Uani 1 1 d . . . . .
C00S C 0.45055(15) 0.75384(15) 0.6506(5) 0.0361(8) Uani 1 1 d . . . . .
H00S H 0.447341 0.780702 0.682038 0.043 Uiso 1 1 calc R U . . .
C00T C 0.61495(15) 0.85300(15) -0.1003(5) 0.0359(9) Uani 1 1 d . . . . .
C00U C 0.33679(14) 0.88591(15) 0.7590(5) 0.0323(8) Uani 1 1 d . . . . .
H00U H 0.311382 0.855106 0.791862 0.039 Uiso 1 1 calc R U . . .
C00V C 0.42538(15) 0.66891(15) 0.6803(5) 0.0352(8) Uani 1 1 d . . . . .
H00V H 0.406166 0.638228 0.728576 0.042 Uiso 1 1 calc R U . . .
C00W C 0.58420(13) 0.79470(13) 0.2943(4) 0.0265(7) Uani 1 1 d . . . . .
C00X C 0.43859(12) 0.86290(13) 0.8677(4) 0.0258(7) Uani 1 1 d . . . . .
C00Y C 0.56293(13) 0.92923(14) 0.6857(5) 0.0289(7) Uani 1 1 d . . . . .
H00Y H 0.596051 0.947954 0.715121 0.035 Uiso 1 1 calc R U . . .
C00Z C 0.42225(16) 0.70902(16) 0.7248(5) 0.0378(9) Uani 1 1 d . . . . .
H00Z H 0.400781 0.706193 0.806219 0.045 Uiso 1 1 calc R U . . .
C010 C 0.36254(17) 0.96187(16) 0.6296(5) 0.0380(9) Uani 1 1 d . . . . .
H010 H 0.354929 0.982913 0.573437 0.046 Uiso 1 1 calc R U . . .
C011 C 0.52686(13) 0.91351(13) 0.7946(4) 0.0260(7) Uani 1 1 d . . . . .
C012 C 0.36880(14) 0.77377(14) 1.1619(5) 0.0316(8) Uani 1 1 d . . . . .
H012 H 0.337399 0.762042 1.205007 0.038 Uiso 1 1 calc R U . . .
C013 C 0.42136(14) 0.94437(15) 0.7395(5) 0.0344(8) Uani 1 1 d . . . . .
H013 H 0.454280 0.953960 0.759957 0.041 Uiso 1 1 calc R U . . .
C014 C 0.54984(14) 0.91707(15) 0.5308(5) 0.0324(8) Uani 1 1 d . . . . .
C015 C 0.48255(14) 0.76013(14) 0.5345(5) 0.0333(8) Uani 1 1 d . . . . .
H015 H 0.500967 0.790735 0.485003 0.040 Uiso 1 1 calc R U . . .
C016 C 0.58686(15) 0.63557(17) 0.1546(5) 0.0380(9) Uani 1 1 d . . . . .
H016 H 0.618754 0.651854 0.112770 0.046 Uiso 1 1 calc R U . . .
C017 C 0.46182(14) 0.80790(14) 1.0297(5) 0.0320(8) Uani 1 1 d . . . . .
H017 H 0.492815 0.818739 0.984519 0.038 Uiso 1 1 calc R U . . .
C018 C 0.60728(13) 0.82938(13) 0.1803(5) 0.0276(7) Uani 1 1 d . . . . .
H018 H 0.632575 0.861031 0.206279 0.033 Uiso 1 1 calc R U . . .
C019 C 0.57014(14) 0.66146(15) 0.2391(5) 0.0343(8) Uani 1 1 d . . . . .
H019 H 0.590770 0.695195 0.256850 0.041 Uiso 1 1 calc R U . . .
C01A C 0.39828(16) 0.75582(15) 1.2103(5) 0.0357(9) Uani 1 1 d . . . . .
H01A H 0.387279 0.731650 1.289092 0.043 Uiso 1 1 calc R U . . .
C01B C 0.55747(17) 0.58628(16) 0.1308(5) 0.0388(9) Uani 1 1 d . . . . .
H01B H 0.569291 0.568683 0.074189 0.047 Uiso 1 1 calc R U . . .
C01C C 0.49385(15) 0.58846(15) 0.2714(5) 0.0355(9) Uani 1 1 d . . . . .
H01C H 0.461582 0.572064 0.310127 0.043 Uiso 1 1 calc R U . . .
C01D C 0.58660(17) 0.9347(2) 0.4041(6) 0.0468(11) Uani 1 1 d . . . . .
C01E C 0.51092(16) 0.56276(15) 0.1897(6) 0.0400(9) Uani 1 1 d . . . . .
H01E H 0.490635 0.528878 0.173910 0.048 Uiso 1 1 calc R U . . .
C01F C 0.41030(17) 0.97571(16) 0.6600(6) 0.0398(9) Uani 1 1 d . . . . .
H01F H 0.435558 1.006549 0.626733 0.048 Uiso 1 1 calc R U . . .
C01G C 0.44459(16) 0.77321(16) 1.1434(5) 0.0367(9) Uani 1 1 d . . . . .
H01G H 0.464279 0.760463 1.178360 0.044 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C00E N008 H008 125.2 . . ?
C00E N008 C00N 109.6(3) . . ?
C00N N008 H008 125.2 . . ?
C00F N009 C00J 119.5(3) . . ?
C00G N00A H00A 125.7 . . ?
C00G N00A C00P 108.6(3) . . ?
C00P N00A H00A 125.7 . . ?
C00I N C00D 119.2(3) . . ?
C00U C00C C00E 120.2(3) . . ?
C013 C00C C00E 120.8(3) . . ?
C013 C00C C00U 119.0(4) . . ?
N C00D C00X 117.7(3) . . ?
N C00D C011 119.2(3) . . ?
C011 C00D C00X 122.9(3) . . ?
N008 C00E C00C 121.6(3) . . ?
N008 C00E C00X 109.1(3) . . ?
C00X C00E C00C 129.2(3) . . ?
N009 C00F H00F 118.6 . . ?
N009 C00F C00O 122.7(4) . . ?
C00O C00F H00F 118.6 . . ?
N00A C00G C00M 110.3(3) . . ?
N00A C00G C00R 120.4(3) . . ?
C00M C00G C00R 129.3(4) . . ?
N C00I H00I 118.2 . . ?
N C00I C014 123.5(4) . . ?
C014 C00I H00I 118.2 . . ?
N009 C00J C00M 118.2(3) . . ?
N009 C00J C00W 119.8(3) . . ?
C00W C00J C00M 121.8(4) . . ?
C00P C00K C00M 106.8(3) . . ?
C00P C00K C015 118.6(4) . . ?
C015 C00K C00M 134.5(4) . . ?
C00N C00L C00X 106.5(3) . . ?
C017 C00L C00N 119.2(3) . . ?
C017 C00L C00X 134.3(4) . . ?
C00G C00M C00J 127.5(4) . . ?
C00G C00M C00K 106.1(3) . . ?
C00K C00M C00J 125.6(3) . . ?
N008 C00N C00L 108.0(3) . . ?
N008 C00N C012 129.7(3) . . ?
C012 C00N C00L 122.3(3) . . ?
C00F C00O C00T 120.1(4) . . ?
C018 C00O C00F 118.7(3) . . ?
C018 C00O C00T 121.2(3) . . ?
N00A C00P C00K 108.2(3) . . ?
N00A C00P C00V 129.0(4) . . ?
C00K C00P C00V 122.8(4) . . ?
C00U C00Q H00Q 119.8 . . ?
C010 C00Q H00Q 119.8 . . ?
C010 C00Q C00U 120.4(4) . . ?
C019 C00R C00G 121.1(3) . . ?
C01C C00R C00G 120.1(4) . . ?
C01C C00R C019 118.7(4) . . ?
C00Z C00S H00S 118.9 . . ?
C015 C00S H00S 118.9 . . ?
C015 C00S C00Z 122.2(4) . . ?
F003 C00T C00O 111.9(4) . . ?
F004 C00T F003 106.3(3) . . ?
F004 C00T C00O 111.7(3) . . ?
F006 C00T F003 106.8(3) . . ?
F006 C00T F004 107.1(4) . . ?
F006 C00T C00O 112.6(3) . . ?
C00C C00U H00U 120.0 . . ?
C00Q C00U C00C 120.0(4) . . ?
C00Q C00U H00U 120.0 . . ?
C00P C00V H00V 121.5 . . ?
C00Z C00V C00P 117.1(4) . . ?
C00Z C00V H00V 121.5 . . ?
C00J C00W Cl 121.1(3) . . ?
C018 C00W Cl 118.4(3) . . ?
C018 C00W C00J 120.6(4) . . ?
C00E C00X C00D 127.2(3) . . ?
C00E C00X C00L 106.8(3) . . ?
C00L C00X C00D 125.3(3) . . ?
C011 C00Y H00Y 120.9 . . ?
C011 C00Y C014 118.2(3) . . ?
C014 C00Y H00Y 120.9 . . ?
C00S C00Z H00Z 119.7 . . ?
C00V C00Z C00S 120.5(4) . . ?
C00V C00Z H00Z 119.7 . . ?
C00Q C010 H010 120.0 . . ?
C00Q C010 C01F 120.1(4) . . ?
C01F C010 H010 120.0 . . ?
C00D C011 Cl1 119.9(3) . . ?
C00Y C011 Cl1 118.6(3) . . ?
C00Y C011 C00D 121.5(3) . . ?
C00N C012 H012 121.2 . . ?
C01A C012 C00N 117.6(4) . . ?
C01A C012 H012 121.2 . . ?
C00C C013 H013 119.6 . . ?
C00C C013 C01F 120.8(4) . . ?
C01F C013 H013 119.6 . . ?
C00I C014 C00Y 118.3(4) . . ?
C00I C014 C01D 119.9(4) . . ?
C00Y C014 C01D 121.7(4) . . ?
C00K C015 H015 120.6 . . ?
C00S C015 C00K 118.7(4) . . ?
C00S C015 H015 120.6 . . ?
C019 C016 H016 119.7 . . ?
C01B C016 H016 119.7 . . ?
C01B C016 C019 120.6(4) . . ?
C00L C017 H017 120.6 . . ?
C01G C017 C00L 118.7(4) . . ?
C01G C017 H017 120.6 . . ?
C00O C018 C00W 118.4(3) . . ?
C00O C018 H018 120.8 . . ?
C00W C018 H018 120.8 . . ?
C00R C019 H019 120.1 . . ?
C016 C019 C00R 119.8(4) . . ?
C016 C019 H019 120.1 . . ?
C012 C01A H01A 119.8 . . ?
C012 C01A C01G 120.4(4) . . ?
C01G C01A H01A 119.8 . . ?
C016 C01B H01B 120.1 . . ?
C01E C01B C016 119.7(4) . . ?
C01E C01B H01B 120.1 . . ?
C00R C01C H01C 119.4 . . ?
C01E C01C C00R 121.2(4) . . ?
C01E C01C H01C 119.4 . . ?
F005 C01D C014 111.3(4) . . ?
F007 C01D F005 103.8(4) . . ?
F007 C01D C014 111.9(4) . . ?
F00H C01D F005 105.6(5) . . ?
F00H C01D F007 110.3(5) . . ?
F00H C01D C014 113.2(4) . . ?
C01B C01E H01E 120.0 . . ?
C01C C01E C01B 120.0(4) . . ?
C01C C01E H01E 120.0 . . ?
C010 C01F C013 119.8(4) . . ?
C010 C01F H01F 120.1 . . ?
C013 C01F H01F 120.1 . . ?
C017 C01G C01A 121.7(4) . . ?
C017 C01G H01G 119.1 . . ?
C01A C01G H01G 119.1 . . ?
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
Cl1 C011 1.736(4) . ?
Cl C00W 1.723(4) . ?
F003 C00T 1.340(5) . ?
F004 C00T 1.338(5) . ?
F005 C01D 1.334(6) . ?
F006 C00T 1.336(5) . ?
F007 C01D 1.332(7) . ?
N008 H008 0.8800 . ?
N008 C00E 1.364(5) . ?
N008 C00N 1.378(5) . ?
N009 C00F 1.330(5) . ?
N009 C00J 1.351(5) . ?
N00A H00A 0.8800 . ?
N00A C00G 1.354(5) . ?
N00A C00P 1.379(5) . ?
N C00D 1.351(5) . ?
N C00I 1.336(5) . ?
C00C C00E 1.477(5) . ?
C00C C00U 1.394(5) . ?
C00C C013 1.385(6) . ?
C00D C00X 1.464(5) . ?
C00D C011 1.406(5) . ?
C00E C00X 1.389(5) . ?
C00F H00F 0.9500 . ?
C00F C00O 1.391(5) . ?
C00G C00M 1.375(5) . ?
C00G C00R 1.490(5) . ?
F00H C01D 1.305(6) . ?
C00I H00I 0.9500 . ?
C00I C014 1.379(6) . ?
C00J C00M 1.472(5) . ?
C00J C00W 1.400(5) . ?
C00K C00M 1.436(5) . ?
C00K C00P 1.392(5) . ?
C00K C015 1.414(6) . ?
C00L C00N 1.408(5) . ?
C00L C00X 1.438(5) . ?
C00L C017 1.400(5) . ?
C00N C012 1.388(5) . ?
C00O C00T 1.488(5) . ?
C00O C018 1.379(6) . ?
C00P C00V 1.409(6) . ?
C00Q H00Q 0.9500 . ?
C00Q C00U 1.393(6) . ?
C00Q C010 1.376(7) . ?
C00R C019 1.396(6) . ?
C00R C01C 1.387(6) . ?
C00S H00S 0.9500 . ?
C00S C00Z 1.403(6) . ?
C00S C015 1.366(6) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C00Z 1.384(6) . ?
C00W C018 1.380(5) . ?
C00Y H00Y 0.9500 . ?
C00Y C011 1.367(5) . ?
C00Y C014 1.389(6) . ?
C00Z H00Z 0.9500 . ?
C010 H010 0.9500 . ?
C010 C01F 1.380(6) . ?
C012 H012 0.9500 . ?
C012 C01A 1.385(6) . ?
C013 H013 0.9500 . ?
C013 C01F 1.392(6) . ?
C014 C01D 1.487(6) . ?
C015 H015 0.9500 . ?
C016 H016 0.9500 . ?
C016 C019 1.389(6) . ?
C016 C01B 1.383(7) . ?
C017 H017 0.9500 . ?
C017 C01G 1.367(6) . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C01A H01A 0.9500 . ?
C01A C01G 1.412(6) . ?
C01B H01B 0.9500 . ?
C01B C01E 1.379(6) . ?
C01C H01C 0.9500 . ?
C01C C01E 1.379(6) . ?
C01E H01E 0.9500 . ?
C01F H01F 0.9500 . ?
C01G H01G 0.9500 . ?
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
Cl C00W C018 C00O -179.8(3) . . . . ?
N008 C00E C00X C00D 169.3(4) . . . . ?
N008 C00E C00X C00L -1.6(4) . . . . ?
N008 C00N C012 C01A -179.7(4) . . . . ?
N009 C00F C00O C00T -178.2(3) . . . . ?
N009 C00F C00O C018 3.5(5) . . . . ?
N009 C00J C00M C00G 51.4(5) . . . . ?
N009 C00J C00M C00K -117.2(4) . . . . ?
N009 C00J C00W Cl -175.8(3) . . . . ?
N009 C00J C00W C018 4.7(5) . . . . ?
N00A C00G C00M C00J -169.1(3) . . . . ?
N00A C00G C00M C00K 1.2(4) . . . . ?
N00A C00G C00R C019 -152.1(4) . . . . ?
N00A C00G C00R C01C 29.3(6) . . . . ?
N00A C00P C00V C00Z -179.9(4) . . . . ?
N C00D C00X C00E -56.4(5) . . . . ?
N C00D C00X C00L 112.9(4) . . . . ?
N C00D C011 Cl1 175.0(3) . . . . ?
N C00D C011 C00Y -2.5(5) . . . . ?
N C00I C014 C00Y -1.7(6) . . . . ?
N C00I C014 C01D -177.6(4) . . . . ?
C00C C00E C00X C00D -13.7(6) . . . . ?
C00C C00E C00X C00L 175.4(4) . . . . ?
C00C C013 C01F C010 -0.2(7) . . . . ?
C00D N C00I C014 0.2(6) . . . . ?
C00E N008 C00N C00L -0.5(4) . . . . ?
C00E N008 C00N C012 179.8(4) . . . . ?
C00E C00C C00U C00Q 179.5(4) . . . . ?
C00E C00C C013 C01F 179.9(4) . . . . ?
C00F N009 C00J C00M 170.1(3) . . . . ?
C00F N009 C00J C00W -5.0(5) . . . . ?
C00F C00O C00T F003 155.8(3) . . . . ?
C00F C00O C00T F004 36.7(5) . . . . ?
C00F C00O C00T F006 -83.8(5) . . . . ?
C00F C00O C018 C00W -3.7(5) . . . . ?
C00G N00A C00P C00K 0.2(4) . . . . ?
C00G N00A C00P C00V -178.6(4) . . . . ?
C00G C00R C019 C016 -178.1(4) . . . . ?
C00G C00R C01C C01E 179.3(4) . . . . ?
C00I N C00D C00X -173.3(3) . . . . ?
C00I N C00D C011 1.9(5) . . . . ?
C00I C014 C01D F005 66.5(6) . . . . ?
C00I C014 C01D F007 -49.2(6) . . . . ?
C00I C014 C01D F00H -174.7(5) . . . . ?
C00J N009 C00F C00O 0.9(5) . . . . ?
C00J C00W C018 C00O -0.3(5) . . . . ?
C00K C00P C00V C00Z 1.4(6) . . . . ?
C00L C00N C012 C01A 0.7(6) . . . . ?
C00L C017 C01G C01A 1.2(7) . . . . ?
C00M C00G C00R C019 26.5(6) . . . . ?
C00M C00G C00R C01C -152.2(4) . . . . ?
C00M C00J C00W Cl 9.3(5) . . . . ?
C00M C00J C00W C018 -170.2(3) . . . . ?
C00M C00K C00P N00A 0.5(4) . . . . ?
C00M C00K C00P C00V 179.4(4) . . . . ?
C00M C00K C015 C00S 179.3(4) . . . . ?
C00N N008 C00E C00C -175.9(3) . . . . ?
C00N N008 C00E C00X 1.3(4) . . . . ?
C00N C00L C00X C00D -169.8(3) . . . . ?
C00N C00L C00X C00E 1.3(4) . . . . ?
C00N C00L C017 C01G -1.4(6) . . . . ?
C00N C012 C01A C01G -0.9(6) . . . . ?
C00P N00A C00G C00M -0.9(4) . . . . ?
C00P N00A C00G C00R 177.9(3) . . . . ?
C00P C00K C00M C00G -1.1(4) . . . . ?
C00P C00K C00M C00J 169.5(4) . . . . ?
C00P C00K C015 C00S 3.0(6) . . . . ?
C00P C00V C00Z C00S 0.8(6) . . . . ?
C00Q C010 C01F C013 1.3(7) . . . . ?
C00R C00G C00M C00J 12.2(7) . . . . ?
C00R C00G C00M C00K -177.4(4) . . . . ?
C00R C01C C01E C01B -1.0(7) . . . . ?
C00T C00O C018 C00W 178.0(3) . . . . ?
C00U C00C C00E N008 -29.3(5) . . . . ?
C00U C00C C00E C00X 154.0(4) . . . . ?
C00U C00C C013 C01F -0.3(6) . . . . ?
C00U C00Q C010 C01F -1.9(7) . . . . ?
C00W C00J C00M C00G -133.7(4) . . . . ?
C00W C00J C00M C00K 57.7(5) . . . . ?
C00X C00D C011 Cl1 -10.1(5) . . . . ?
C00X C00D C011 C00Y 172.5(3) . . . . ?
C00X C00L C00N N008 -0.5(4) . . . . ?
C00X C00L C00N C012 179.2(4) . . . . ?
C00X C00L C017 C01G -179.7(4) . . . . ?
C00Y C014 C01D F005 -109.3(5) . . . . ?
C00Y C014 C01D F007 135.1(4) . . . . ?
C00Y C014 C01D F00H 9.6(7) . . . . ?
C00Z C00S C015 C00K -0.9(7) . . . . ?
C010 C00Q C00U C00C 1.4(6) . . . . ?
C011 C00D C00X C00E 128.6(4) . . . . ?
C011 C00D C00X C00L -62.1(5) . . . . ?
C011 C00Y C014 C00I 1.1(6) . . . . ?
C011 C00Y C014 C01D 176.9(4) . . . . ?
C012 C01A C01G C017 -0.1(7) . . . . ?
C013 C00C C00E N008 150.5(4) . . . . ?
C013 C00C C00E C00X -26.2(6) . . . . ?
C013 C00C C00U C00Q -0.3(6) . . . . ?
C014 C00Y C011 Cl1 -176.5(3) . . . . ?
C014 C00Y C011 C00D 0.9(6) . . . . ?
C015 C00K C00M C00G -177.6(4) . . . . ?
C015 C00K C00M C00J -7.0(7) . . . . ?
C015 C00K C00P N00A 177.7(3) . . . . ?
C015 C00K C00P C00V -3.4(6) . . . . ?
C015 C00S C00Z C00V -1.0(7) . . . . ?
C016 C01B C01E C01C 0.2(7) . . . . ?
C017 C00L C00N N008 -179.2(3) . . . . ?
C017 C00L C00N C012 0.4(6) . . . . ?
C017 C00L C00X C00D 8.6(7) . . . . ?
C017 C00L C00X C00E 179.8(4) . . . . ?
C018 C00O C00T F003 -25.9(5) . . . . ?
C018 C00O C00T F004 -145.0(4) . . . . ?
C018 C00O C00T F006 94.5(5) . . . . ?
C019 C00R C01C C01E 0.6(6) . . . . ?
C019 C016 C01B C01E 0.9(7) . . . . ?
C01B C016 C019 C00R -1.3(6) . . . . ?
C01C C00R C019 C016 0.5(6) . . . . ?
