#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:16:44 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296290 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/38/7133838.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_7133838
loop_
_publ_author_name
'Dhake, Kushal'
'Woelk, Kyla J.'
'Krueckl, Liam D. N.'
'Alberts, Faith'
'Mutter, James'
'Pohl, Matthew O.'
'Thomas, Gilian T.'
'Sharma, Muskan'
'Bjornerud-Brown, Jaelyn'
'Fernández, Nahiane Pipaón'
'Schley, Nathan D.'
'Leitch, David C.'
_publ_section_title
;
 Diastereoselective dearomative cycloaddition of bicyclobutanes with
 pyridinium ylides: a modular approach to multisubstituted
 azabicyclo[3.1.1]heptanes.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13008
_journal_page_last               13011
_journal_paper_doi               10.1039/d4cc04730c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C H2 Cl2, C24 H24 F N3 O3'
_chemical_formula_sum            'C25 H26 Cl2 F N3 O3'
_chemical_formula_weight         506.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-30 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                109.987(4)
_cell_angle_beta                 96.545(3)
_cell_angle_gamma                110.033(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8105(3)
_cell_length_b                   10.5343(4)
_cell_length_c                   13.5571(6)
_cell_measurement_reflns_used    9156
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5620
_cell_measurement_theta_min      3.5740
_cell_volume                     1193.91(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_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 -19.00   1.00    1.00    --  -35.84 -57.00-150.00   84
  2  ω    -55.00  33.00   1.00    1.00    --  -35.84  38.00   0.00   88
  3  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00 120.00   88
  4  ω    -55.00  33.00   1.00    1.00    --  -35.84  38.00   0.00   88
  5  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00  90.00   95
  6  ω      8.00  42.00   1.00    1.00    --   35.84  79.00 140.70   34
  7  ω      9.00  42.00   1.00    1.00    --   35.84  77.00 -10.84   33
  8  ω      9.00  42.00   1.00    1.00    --   35.84  77.00-178.25   33
  9  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  30.00   84
 10  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00 -90.00   84
 11  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00 -90.00   84
 12  ω      9.00  42.00   1.00    1.00    --   35.84  78.00 -55.99   33
 13  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00-120.00   84
 14  ω      9.00  42.00   1.00    1.00    --   35.84  78.00  43.89   33
 15  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  30.00   84
 16  ω      9.00  42.00   1.00    1.00    --   35.84  78.00-131.57   33
 17  ω     41.00 135.00   1.00    8.00    --  108.40 -77.00 -30.00   94
 18  ω     40.00 126.00   1.00    8.00    --  108.40 -45.00 150.00   86
 19  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00  64.60   95
 20  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00 -30.00   92
 21  ω     87.00 178.00   1.00    8.00    --  108.40  30.00-120.00   91
 22  ω    103.00 176.00   1.00    8.00    --  108.40  77.00 150.00   73
 23  ω     91.00 177.00   1.00    8.00    --  108.40  45.00  60.00   86
 24  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00-120.00   92
 25  ω     41.00 137.00   1.00    8.00    --  108.40 -80.00-149.71   96
 26  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00   6.98   95
 27  ω     91.00 177.00   1.00    8.00    --  108.40  45.00 120.00   86
 28  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00  60.00   92
 29  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00  35.94   95
 30  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00 -86.44   95
 31  ω     41.00 137.00   1.00    8.00    --  108.40 -80.00 147.40   96
 32  ω   -103.00 -19.00   1.00    1.00    --  -35.84 -57.00 -90.00   84
 33  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00   0.00   95
 34  ω   -103.00 -19.00   1.00    1.00    --  -35.84 -57.00 -60.00   84
 35  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00-120.00   95
 36  ω    -53.00  31.00   1.00    1.00    --  -35.84  57.00-180.00   84
 37  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00-150.00   88
 38  ω    -53.00  31.00   1.00    1.00    --  -35.84  57.00  30.00   84
 39  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00  30.00   88
 40  ω     19.00 103.00   1.00    1.00    --   35.84  57.00 120.00   84
 41  ω     10.00  36.00   1.00    1.00    --   35.84  75.00 -90.78   26
 42  ω    -21.00  63.00   1.00    1.00    --   35.84 -77.00 120.00   84
 43  ω      9.00  42.00   1.00    1.00    --   35.84  78.00  99.48   33
 44  ω     87.00 178.00   1.00    8.00    --  108.40  30.00   0.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1295121000
_diffrn_orient_matrix_UB_12      -0.0450851000
_diffrn_orient_matrix_UB_13      -0.0268719000
_diffrn_orient_matrix_UB_21      -0.0121197000
_diffrn_orient_matrix_UB_22      -0.0688876000
_diffrn_orient_matrix_UB_23      0.0839742000
_diffrn_orient_matrix_UB_31      -0.1143307000
_diffrn_orient_matrix_UB_32      -0.1493063000
_diffrn_orient_matrix_UB_33      -0.0890084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4533
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.732
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0659
_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)+5.1172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4016
_reflns_number_total             4533
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc04730c2.cif
_cod_data_source_block           kjw-2024-220
_cod_depositor_comments
'Adding full bibliography for 7133838--7133839.cif.'
_cod_original_cell_volume        1193.91(9)
_cod_database_code               7133838
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23.5H26Cl2N4.5O4
_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   0.896
_shelx_estimated_absorpt_t_min   0.679
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.738(4)
 0.262(4)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C4(H4A,H4B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C20(H20)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2024-06-03
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.864
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.45575(14) 0.68432(14) 1.00347(11) 0.0334(3) Uani 1 1 d . . . . .
Cl2 Cl 0.13927(16) 0.59188(17) 0.90170(11) 0.0440(4) Uani 1 1 d . . . . .
C25 C 0.2690(6) 0.5896(6) 1.0024(4) 0.0314(11) Uani 1 1 d . . . . .
H25A H 0.253440 0.636040 1.074689 0.038 Uiso 1 1 calc R U . . .
H25B H 0.250294 0.485745 0.988670 0.038 Uiso 1 1 calc R U . . .
F1 F 1.0353(3) 0.1836(3) 0.3059(2) 0.0231(6) Uani 1 1 d . . . . .
O1 O 0.7594(4) 0.1974(3) 0.7471(2) 0.0211(7) Uani 1 1 d . . . . .
O2 O 0.7059(3) 0.0505(3) 0.5701(2) 0.0164(6) Uani 1 1 d . . . . .
O3 O 0.5884(3) 0.7236(3) 0.6949(2) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.5128(4) 0.2674(4) 0.6815(3) 0.0157(7) Uani 1 1 d . . . . .
N2 N 0.7178(4) 0.7641(4) 0.8603(3) 0.0144(7) Uani 1 1 d . . . . .
N3 N 0.8081(4) 0.7216(4) 0.9167(3) 0.0151(7) Uani 1 1 d . . . . .
C1 C 0.6993(4) 0.1597(4) 0.6533(3) 0.0137(8) Uani 1 1 d . . . . .
C2 C 0.6067(4) 0.2303(4) 0.6107(3) 0.0122(8) Uani 1 1 d . . . . .
H2 H 0.539717 0.156973 0.537102 0.015 Uiso 1 1 calc R U . . .
C3 C 0.7111(4) 0.3692(4) 0.5991(3) 0.0123(8) Uani 1 1 d . . . . .
C4 C 0.6139(4) 0.4514(4) 0.5790(3) 0.0126(8) Uani 1 1 d . . . . .
H4A H 0.658086 0.522206 0.546779 0.015 Uiso 1 1 calc R U . . .
H4B H 0.507400 0.385748 0.539546 0.015 Uiso 1 1 calc R U . . .
C5 C 0.6427(4) 0.5229(4) 0.7041(3) 0.0121(8) Uani 1 1 d . . . . .
C6 C 0.7888(4) 0.4962(4) 0.7140(3) 0.0131(8) Uani 1 1 d . . . . .
H6A H 0.879185 0.578852 0.717410 0.016 Uiso 1 1 calc R U . . .
H6B H 0.808517 0.462968 0.772113 0.016 Uiso 1 1 calc R U . . .
C7 C 0.5291(4) 0.4201(4) 0.7415(3) 0.0123(8) Uani 1 1 d . . . . .
H7 H 0.570536 0.449621 0.820623 0.015 Uiso 1 1 calc R U . . .
C8 C 0.3753(5) 0.4215(5) 0.7254(3) 0.0174(9) Uani 1 1 d . . . . .
H8 H 0.360973 0.502632 0.717642 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2588(5) 0.3053(5) 0.7225(4) 0.0186(9) Uani 1 1 d . . . . .
H9 H 0.164362 0.310810 0.724107 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2750(5) 0.1721(5) 0.7168(4) 0.0193(9) Uani 1 1 d . . . . .
H10 H 0.202683 0.099476 0.732086 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3975(5) 0.1552(5) 0.6888(4) 0.0173(8) Uani 1 1 d . . . . .
H11 H 0.403881 0.062722 0.673686 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8022(5) 0.3303(4) 0.5211(3) 0.0138(8) Uani 1 1 d . . . . .
C13 C 0.9484(5) 0.3475(4) 0.5586(4) 0.0163(8) Uani 1 1 d . . . . .
H13 H 0.994093 0.392657 0.634577 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0285(5) 0.2999(5) 0.4869(4) 0.0176(9) Uani 1 1 d . . . . .
H14 H 1.127933 0.311095 0.512565 0.021 Uiso 1 1 calc R U . . .
C15 C 0.9592(5) 0.2360(5) 0.3776(4) 0.0173(9) Uani 1 1 d . . . . .
C16 C 0.8173(5) 0.2216(5) 0.3362(4) 0.0182(9) Uani 1 1 d . . . . .
H16 H 0.774496 0.180621 0.259996 0.022 Uiso 1 1 calc R U . . .
C17 C 0.7385(5) 0.2690(5) 0.4094(3) 0.0166(8) Uani 1 1 d . . . . .
H17 H 0.640029 0.259449 0.382929 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6468(4) 0.6770(4) 0.7500(3) 0.0130(8) Uani 1 1 d . . . . .
C19 C 0.7176(5) 0.8989(4) 0.9244(3) 0.0164(8) Uani 1 1 d . . . . .
C20 C 0.8116(5) 0.9424(5) 1.0232(3) 0.0184(9) Uani 1 1 d . . . . .
H20 H 0.836543 1.030612 1.085839 0.022 Uiso 1 1 calc R U . . .
C21 C 0.8651(5) 0.8308(5) 1.0144(3) 0.0166(8) Uani 1 1 d . . . . .
C22 C 0.9721(5) 0.8265(5) 1.0995(3) 0.0202(9) Uani 1 1 d . . . . .
H22A H 0.916794 0.784693 1.144641 0.030 Uiso 1 1 calc R U . . .
H22B H 1.046896 0.927200 1.145142 0.030 Uiso 1 1 calc R U . . .
H22C H 1.023022 0.764948 1.064527 0.030 Uiso 1 1 calc R U . . .
C23 C 0.6247(6) 0.9696(5) 0.8891(4) 0.0235(10) Uani 1 1 d . . . . .
H23A H 0.658309 0.997564 0.831271 0.035 Uiso 1 1 calc R U . . .
H23B H 0.635905 1.058083 0.951044 0.035 Uiso 1 1 calc R U . . .
H23C H 0.518875 0.899509 0.861734 0.035 Uiso 1 1 calc R U . . .
C24 C 0.7991(5) -0.0206(5) 0.5963(4) 0.0225(10) Uani 1 1 d . . . . .
H24A H 0.797878 -0.096612 0.529312 0.034 Uiso 1 1 calc R U . . .
H24B H 0.759964 -0.066643 0.644711 0.034 Uiso 1 1 calc R U . . .
H24C H 0.902426 0.053398 0.632683 0.034 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 3 6 0.0229
3 -3 -6 0.0129
-3 7 -2 0.0604
5 -2 5 0.0365
4 -7 2 0.0421
-2 -3 -3 0.0667
-5 -1 5 0.0601
6 -2 -5 0.0095
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
Cl1 C25 Cl2 111.8(3) . . ?
Cl1 C25 H25A 109.3 . . ?
Cl1 C25 H25B 109.3 . . ?
Cl2 C25 H25A 109.3 . . ?
Cl2 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C1 O2 C24 116.5(3) . . ?
C2 N1 C7 123.4(3) . . ?
C11 N1 C2 118.9(3) . . ?
C11 N1 C7 117.7(3) . . ?
N3 N2 C18 119.6(3) . . ?
N3 N2 C19 112.3(3) . . ?
C19 N2 C18 128.1(3) . . ?
C21 N3 N2 104.2(3) . . ?
O1 C1 O2 124.6(4) . . ?
O1 C1 C2 125.7(4) . . ?
O2 C1 C2 109.7(3) . . ?
N1 C2 C1 111.1(3) . . ?
N1 C2 H2 108.3 . . ?
N1 C2 C3 110.5(3) . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 110.4(3) . . ?
C3 C2 H2 108.3 . . ?
C2 C3 C4 107.1(3) . . ?
C2 C3 C6 108.7(3) . . ?
C4 C3 C6 88.2(3) . . ?
C12 C3 C2 110.8(3) . . ?
C12 C3 C4 119.1(3) . . ?
C12 C3 C6 120.5(3) . . ?
C3 C4 H4A 114.3 . . ?
C3 C4 H4B 114.3 . . ?
H4A C4 H4B 111.4 . . ?
C5 C4 C3 86.3(3) . . ?
C5 C4 H4A 114.3 . . ?
C5 C4 H4B 114.3 . . ?
C4 C5 C6 88.3(3) . . ?
C7 C5 C4 110.1(3) . . ?
C7 C5 C6 108.8(3) . . ?
C18 C5 C4 115.2(3) . . ?
C18 C5 C6 121.5(3) . . ?
C18 C5 C7 110.9(3) . . ?
C3 C6 C5 86.0(3) . . ?
C3 C6 H6A 114.3 . . ?
C3 C6 H6B 114.3 . . ?
C5 C6 H6A 114.3 . . ?
C5 C6 H6B 114.3 . . ?
H6A C6 H6B 111.5 . . ?
N1 C7 C5 108.5(3) . . ?
N1 C7 H7 108.3 . . ?
N1 C7 C8 108.3(3) . . ?
C5 C7 H7 108.3 . . ?
C8 C7 C5 115.1(3) . . ?
C8 C7 H7 108.3 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(4) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.2(4) . . ?
C11 C10 H10 121.4 . . ?
N1 C11 H11 119.1 . . ?
C10 C11 N1 121.9(4) . . ?
C10 C11 H11 119.0 . . ?
C13 C12 C3 120.9(4) . . ?
C17 C12 C3 120.2(4) . . ?
C17 C12 C13 118.8(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.8(4) . . ?
C15 C14 H14 121.1 . . ?
F1 C15 C16 118.3(4) . . ?
C14 C15 F1 118.4(4) . . ?
C14 C15 C16 123.3(4) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 117.9(4) . . ?
C17 C16 H16 121.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
O3 C18 N2 120.6(4) . . ?
O3 C18 C5 122.1(4) . . ?
N2 C18 C5 117.3(3) . . ?
N2 C19 C23 125.0(4) . . ?
C20 C19 N2 104.9(4) . . ?
C20 C19 C23 130.0(4) . . ?
C19 C20 H20 126.5 . . ?
C19 C20 C21 106.9(4) . . ?
C21 C20 H20 126.5 . . ?
N3 C21 C20 111.7(4) . . ?
N3 C21 C22 120.3(4) . . ?
C20 C21 C22 128.0(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 C25 1.756(5) . ?
Cl2 C25 1.770(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
F1 C15 1.374(5) . ?
O1 C1 1.203(5) . ?
O2 C1 1.334(5) . ?
O2 C24 1.449(5) . ?
O3 C18 1.214(5) . ?
N1 C2 1.454(5) . ?
N1 C7 1.475(5) . ?
N1 C11 1.369(5) . ?
N2 N3 1.386(5) . ?
N2 C18 1.396(5) . ?
N2 C19 1.389(5) . ?
N3 C21 1.318(6) . ?
C1 C2 1.532(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.544(5) . ?
C3 C4 1.549(5) . ?
C3 C6 1.551(5) . ?
C3 C12 1.502(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.547(5) . ?
C5 C6 1.553(5) . ?
C5 C7 1.533(5) . ?
C5 C18 1.511(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C7 C8 1.505(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.343(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.442(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.351(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(6) . ?
C12 C17 1.392(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.373(6) . ?
C15 C16 1.378(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(6) . ?
C17 H17 0.9500 . ?
C19 C20 1.365(6) . ?
C19 C23 1.491(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.418(6) . ?
C21 C22 1.493(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C15 C16 C17 177.3(4) . . . . ?
O1 C1 C2 N1 -40.0(6) . . . . ?
O1 C1 C2 C3 82.9(5) . . . . ?
O2 C1 C2 N1 141.1(3) . . . . ?
O2 C1 C2 C3 -96.0(4) . . . . ?
N1 C2 C3 C4 -45.4(4) . . . . ?
N1 C2 C3 C6 48.7(4) . . . . ?
N1 C2 C3 C12 -176.8(3) . . . . ?
N1 C7 C8 C9 37.3(5) . . . . ?
N2 N3 C21 C20 1.0(5) . . . . ?
N2 N3 C21 C22 -179.0(4) . . . . ?
N2 C19 C20 C21 0.0(5) . . . . ?
N3 N2 C18 O3 -167.6(4) . . . . ?
N3 N2 C18 C5 14.0(5) . . . . ?
N3 N2 C19 C20 0.6(5) . . . . ?
N3 N2 C19 C23 -176.3(4) . . . . ?
C1 C2 C3 C4 -168.6(3) . . . . ?
C1 C2 C3 C6 -74.6(4) . . . . ?
C1 C2 C3 C12 60.0(4) . . . . ?
C2 N1 C7 C5 7.4(5) . . . . ?
C2 N1 C7 C8 133.0(4) . . . . ?
C2 N1 C11 C10 -154.6(4) . . . . ?
C2 C3 C4 C5 84.1(3) . . . . ?
C2 C3 C6 C5 -82.7(3) . . . . ?
C2 C3 C12 C13 -96.7(4) . . . . ?
C2 C3 C12 C17 80.0(4) . . . . ?
C3 C4 C5 C6 24.9(3) . . . . ?
C3 C4 C5 C7 -84.5(3) . . . . ?
C3 C4 C5 C18 149.2(3) . . . . ?
C3 C12 C13 C14 174.3(4) . . . . ?
C3 C12 C17 C16 -174.9(4) . . . . ?
C4 C3 C6 C5 24.8(3) . . . . ?
C4 C3 C12 C13 138.4(4) . . . . ?
C4 C3 C12 C17 -44.9(5) . . . . ?
C4 C5 C6 C3 -24.9(3) . . . . ?
C4 C5 C7 N1 42.8(4) . . . . ?
C4 C5 C7 C8 -78.6(4) . . . . ?
C4 C5 C18 O3 21.5(6) . . . . ?
C4 C5 C18 N2 -160.1(3) . . . . ?
C5 C7 C8 C9 159.0(4) . . . . ?
C6 C3 C4 C5 -24.9(3) . . . . ?
C6 C3 C12 C13 31.7(6) . . . . ?
C6 C3 C12 C17 -151.6(4) . . . . ?
C6 C5 C7 N1 -52.4(4) . . . . ?
C6 C5 C7 C8 -173.8(3) . . . . ?
C6 C5 C18 O3 125.9(4) . . . . ?
C6 C5 C18 N2 -55.8(5) . . . . ?
C7 N1 C2 C1 117.1(4) . . . . ?
C7 N1 C2 C3 -5.8(5) . . . . ?
C7 N1 C11 C10 21.8(6) . . . . ?
C7 C5 C6 C3 85.8(3) . . . . ?
C7 C5 C18 O3 -104.4(4) . . . . ?
C7 C5 C18 N2 73.9(4) . . . . ?
C7 C8 C9 C10 -10.0(6) . . . . ?
C8 C9 C10 C11 -15.4(7) . . . . ?
C9 C10 C11 N1 9.4(7) . . . . ?
C11 N1 C2 C1 -66.8(5) . . . . ?
C11 N1 C2 C3 170.4(4) . . . . ?
C11 N1 C7 C5 -168.8(4) . . . . ?
C11 N1 C7 C8 -43.2(5) . . . . ?
C12 C3 C4 C5 -149.3(4) . . . . ?
C12 C3 C6 C5 148.0(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C12 C17 C16 1.9(6) . . . . ?
C13 C14 C15 F1 -177.8(4) . . . . ?
C13 C14 C15 C16 2.2(6) . . . . ?
C14 C15 C16 C17 -2.7(6) . . . . ?
C15 C16 C17 C12 0.6(6) . . . . ?
C17 C12 C13 C14 -2.4(6) . . . . ?
C18 N2 N3 C21 175.7(4) . . . . ?
C18 N2 C19 C20 -175.7(4) . . . . ?
C18 N2 C19 C23 7.4(7) . . . . ?
C18 C5 C6 C3 -143.6(4) . . . . ?
C18 C5 C7 N1 171.5(3) . . . . ?
C18 C5 C7 C8 50.0(5) . . . . ?
C19 N2 N3 C21 -1.0(4) . . . . ?
C19 N2 C18 O3 8.5(6) . . . . ?
C19 N2 C18 C5 -169.8(4) . . . . ?
C19 C20 C21 N3 -0.6(5) . . . . ?
C19 C20 C21 C22 179.3(4) . . . . ?
C23 C19 C20 C21 176.6(4) . . . . ?
C24 O2 C1 O1 -3.3(6) . . . . ?
C24 O2 C1 C2 175.6(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.738(4)
2 0.262(4)
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
-2.9385 3.0981 5.9656 -0.6806 0.3231 -0.6576
2.9385 -3.0981 -5.9656 0.6806 -0.3231 0.6576
-3.4442 6.6612 -2.0613 -0.6910 -0.5902 -0.4173
4.7776 -2.3950 4.8192 0.5972 0.5118 -0.6176
3.7855 -6.5555 2.4848 0.7191 0.6144 0.3248
-2.2650 -2.8850 -3.4359 -0.0709 -0.0623 0.9955
-5.1730 -1.2460 5.0859 -0.7505 0.5756 0.3248
5.7310 -1.7306 -4.5605 0.9428 -0.3332 0.0091
