#------------------------------------------------------------------------------
#$Date: 2022-02-16 01:09:51 +0200 (Wed, 16 Feb 2022) $
#$Revision: 272977 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/63/1566364.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_1566364
loop_
_publ_author_name
'Tan, Jin-Fay'
'Bormann, Carl Thomas'
'Severin, Kay'
'Cramer, Nicolai'
_publ_section_title
;
 Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl
 triazenes from alkynyl triazenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00294A
_journal_year                    2022
_chemical_formula_moiety         'C15 H21 F2 N3 O'
_chemical_formula_sum            'C15 H21 F2 N3 O'
_chemical_formula_weight         297.35
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-13 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                104.216(2)
_cell_angle_beta                 114.117(2)
_cell_angle_gamma                101.164(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5957(2)
_cell_length_b                   9.9111(3)
_cell_length_c                   10.2433(2)
_cell_measurement_reflns_used    8522
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.4200
_cell_measurement_theta_min      4.8760
_cell_volume                     812.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  88.00   0.50    0.50    --   65.75  15.00 120.00   88
  2  ω     49.00  88.00   0.50    1.00    --   76.97  15.00  90.00   78
  3  ω     54.00 108.00   0.50    1.00    --   76.97  15.00  30.00  108
  4  ω     67.00  93.00   0.50    1.00    --   76.97  15.00 -30.00   52
  5  ω     65.00 110.00   0.50    1.00    --   76.97   0.00 -90.00   90
  6  ω     40.00 106.00   0.50    0.50    --   65.75  15.00-120.00  132
  7  ω     39.00 100.00   0.50    0.50    --   65.75   0.00-150.00  122
  8  ω     53.00 117.00   0.50    1.00    --   76.97  15.00-180.00  128
  9  ω     39.00  86.00   0.50    0.50    --   65.75   0.00 -90.00   94
 10  ω     43.00  97.00   0.50    0.50    --   65.75   0.00 -30.00  108
 11  ω     49.00 108.00   0.50    1.00    --   76.97   0.00 -30.00  118
 12  ω     40.00  91.00   0.50    1.00    --   76.97-111.00  77.00  102
 13  ω     52.00  93.00   0.50    1.00    --   76.97-125.00 150.00   82
 14  ω     73.00  98.00   0.50    0.50    --   73.19-125.00 120.00   50
 15  ω     55.00 102.00   0.50    1.00    --   76.97-125.00  60.00   94
 16  ω     42.00  71.00   0.50    1.00    --   76.97-125.00  30.00   58
 17  ω     36.00 101.00   0.50    1.00    --   76.97-125.00 -30.00  130
 18  ω     31.00  63.00   0.50    0.50    --   65.75-125.00 -60.00   64
 19  ω     52.00 102.00   0.50    1.00    --   76.97-125.00   0.00  100
 20  ω     42.00 100.00   0.50    1.00    --   76.97-125.00 -60.00  116
 21  ω     37.00 101.00   0.50    1.00    --   76.97-125.00 -90.00  128
 22  ω     36.00 101.00   0.50    1.00    --   76.97-125.00-150.00  130
 23  ω     49.00 102.00   0.50    1.00    --   76.97-125.00-180.00  106
 24  ω     71.00 102.00   0.50    1.00    --   76.97-125.00-120.00   62
 25  ω     41.00  66.00   0.50    1.00    --   76.97-125.00-120.00   50
 26  ω     76.00 102.00   0.50    1.00    --   76.97-125.00  30.00   52
 27  ω     38.00  63.00   0.50    0.50    --   73.19-111.00  77.00   50
 28  ω     35.00  79.00   0.50    0.50    --   65.75-111.00  77.00   88
 29  ω     36.00 102.00   0.50    1.00    --   76.97-125.00 120.00  132
 30  ω   -111.00 -62.00   0.50    0.50    --  -73.25 147.00 125.61   98
 31  ω   -108.00 -79.00   0.50    0.50    --  -73.25 146.00  73.70   58
 32  ω    -64.00 -38.00   0.50    0.50    --  -67.30 125.00  60.00   52
 33  ω    -80.00 -55.00   0.50    0.50    --  -67.30 111.00 171.00   50
 34  ω    -92.00 -28.00   0.50    0.50    --  -67.30 125.00 -60.00  128
 35  ω    -92.00 -46.00   0.50    0.50    --  -67.30 125.00 -90.00   92
 36  ω    -92.00 -58.00   0.50    0.50    --  -67.30 125.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0770561000
_diffrn_orient_matrix_UB_12      0.0944699000
_diffrn_orient_matrix_UB_13      0.0738742000
_diffrn_orient_matrix_UB_21      -0.0943365000
_diffrn_orient_matrix_UB_22      -0.1370443000
_diffrn_orient_matrix_UB_23      0.0118288000
_diffrn_orient_matrix_UB_31      0.1412205000
_diffrn_orient_matrix_UB_32      0.0345936000
_diffrn_orient_matrix_UB_33      0.1602057000
_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  0.0085
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12419
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.125
_diffrn_reflns_theta_min         4.880
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0030(5)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0356
_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)+(0.0433P)²+0.2384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3033
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00294a2.cif
_cod_data_source_block           jft-r478
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1566364
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C15 H21 F2 N3 O'
_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   0.969
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 98.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.839
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
F1 F 0.49832(8) 0.28352(8) 0.81733(9) 0.0406(2) Uani 1 1 d . . . . .
F2 F 0.31896(10) 0.07292(8) 0.64205(10) 0.0475(2) Uani 1 1 d . . . . .
O1 O 0.20355(12) 0.21152(9) 0.45655(10) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.34780(11) 0.43982(10) 0.66187(10) 0.0256(2) Uani 1 1 d . . . . .
N2 N 0.28940(10) 0.50105(9) 0.56150(10) 0.0248(2) Uani 1 1 d . . . . .
N3 N 0.33925(10) 0.64294(9) 0.61528(10) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.28697(13) 0.28751(12) 0.59096(13) 0.0281(2) Uani 1 1 d . . . . .
C2 C 0.33480(14) 0.21549(12) 0.71302(14) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.23680(13) 0.22019(12) 0.79587(13) 0.0277(2) Uani 1 1 d . . . . .
C4 C 0.10616(14) 0.09844(12) 0.75502(14) 0.0325(3) Uani 1 1 d . . . . .
H4 H 0.079623 0.008988 0.675512 0.039 Uiso 1 1 calc R U . . .
C5 C 0.01512(14) 0.10785(13) 0.83027(14) 0.0355(3) Uani 1 1 d . . . . .
H5 H -0.073753 0.024215 0.801572 0.043 Uiso 1 1 calc R U . . .
C6 C 0.05102(15) 0.23722(13) 0.94706(14) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.18103(14) 0.35898(13) 0.98529(13) 0.0332(3) Uani 1 1 d . . . . .
H7 H 0.206966 0.448767 1.064081 0.040 Uiso 1 1 calc R U . . .
C8 C 0.27245(13) 0.35124(12) 0.91072(13) 0.0298(2) Uani 1 1 d . . . . .
H8 H 0.359852 0.435494 0.937813 0.036 Uiso 1 1 calc R U . . .
C9 C -0.04623(19) 0.24672(17) 1.03081(19) 0.0519(4) Uani 1 1 d . . . . .
H9A H 0.013103 0.237661 1.130237 0.078 Uiso 1 1 calc R U . . .
H9B H -0.150632 0.166715 0.969638 0.078 Uiso 1 1 calc R U . . .
H9C H -0.064492 0.341973 1.047084 0.078 Uiso 1 1 calc R U . . .
C10 C 0.45487(14) 0.73466(12) 0.77838(13) 0.0323(3) Uani 1 1 d . . . . .
H10 H 0.504016 0.669080 0.829186 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3625(2) 0.79325(17) 0.85548(16) 0.0529(4) Uani 1 1 d . . . . .
H11A H 0.314134 0.859159 0.808759 0.079 Uiso 1 1 calc R U . . .
H11B H 0.436706 0.847880 0.965142 0.079 Uiso 1 1 calc R U . . .
H11C H 0.276780 0.710615 0.842435 0.079 Uiso 1 1 calc R U . . .
C12 C 0.59092(17) 0.85495(15) 0.79288(17) 0.0488(4) Uani 1 1 d . . . . .
H12A H 0.641435 0.810855 0.735478 0.073 Uiso 1 1 calc R U . . .
H12B H 0.672012 0.906220 0.901290 0.073 Uiso 1 1 calc R U . . .
H12C H 0.547242 0.925503 0.751255 0.073 Uiso 1 1 calc R U . . .
C13 C 0.26243(13) 0.71182(12) 0.50391(13) 0.0291(2) Uani 1 1 d . . . . .
H13 H 0.294281 0.819371 0.562609 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3259(2) 0.6979(2) 0.38998(18) 0.0567(4) Uani 1 1 d . . . . .
H14A H 0.443587 0.746193 0.444886 0.085 Uiso 1 1 calc R U . . .
H14B H 0.275592 0.745196 0.318178 0.085 Uiso 1 1 calc R U . . .
H14C H 0.299603 0.593287 0.333017 0.085 Uiso 1 1 calc R U . . .
C15 C 0.07970(16) 0.64749(18) 0.42748(19) 0.0517(4) Uani 1 1 d . . . . .
H15A H 0.044748 0.542112 0.367748 0.077 Uiso 1 1 calc R U . . .
H15B H 0.031071 0.698408 0.359123 0.077 Uiso 1 1 calc R U . . .
H15C H 0.045046 0.660322 0.506107 0.077 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'
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
2 -1 -2 0.0238
-2 1 2 0.0114
1 0 0 0.1175
-1 -1 1 0.0396
1 1 -1 0.0340
0 -1 0 0.0395
0 1 0 0.0144
-1 -1 2 0.0782
-5 -3 4 0.0293
0 -2 1 0.0791
1 -2 0 0.0682
0 1 -2 0.1227
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
N2 N1 C1 110.08(9) . . ?
N3 N2 N1 115.20(8) . . ?
N2 N3 C10 124.04(9) . . ?
N2 N3 C13 115.03(8) . . ?
C10 N3 C13 120.77(8) . . ?
O1 C1 N1 129.90(11) . . ?
O1 C1 C2 120.21(10) . . ?
N1 C1 C2 109.84(9) . . ?
F1 C2 C1 109.37(9) . . ?
F1 C2 C3 110.07(9) . . ?
F2 C2 F1 105.13(9) . . ?
F2 C2 C1 108.08(9) . . ?
F2 C2 C3 110.50(9) . . ?
C3 C2 C1 113.34(9) . . ?
C4 C3 C2 121.37(10) . . ?
C8 C3 C2 119.20(10) . . ?
C8 C3 C4 119.35(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.96(11) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.34(11) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 118.03(11) . . ?
C5 C6 C9 121.36(11) . . ?
C7 C6 C9 120.61(12) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.21(11) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.09(10) . . ?
C7 C8 H8 120.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 107.7 . . ?
N3 C10 C11 108.91(10) . . ?
N3 C10 C12 111.22(10) . . ?
C11 C10 H10 107.7 . . ?
C11 C10 C12 113.34(11) . . ?
C12 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13 107.6 . . ?
N3 C13 C14 110.28(10) . . ?
N3 C13 C15 110.60(9) . . ?
C14 C13 H13 107.6 . . ?
C14 C13 C15 112.82(12) . . ?
C15 C13 H13 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
F1 C2 1.3873(14) . ?
F2 C2 1.3675(13) . ?
O1 C1 1.2084(14) . ?
N1 N2 1.3064(13) . ?
N1 C1 1.3860(13) . ?
N2 N3 1.2859(12) . ?
N3 C10 1.4823(13) . ?
N3 C13 1.4836(14) . ?
C1 C2 1.5426(16) . ?
C2 C3 1.5022(16) . ?
C3 C4 1.3929(15) . ?
C3 C8 1.3916(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3830(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3902(17) . ?
C6 C7 1.3970(17) . ?
C6 C9 1.5047(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3798(17) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.5144(19) . ?
C10 C12 1.5164(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.5119(17) . ?
C13 C15 1.5146(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 C2 C3 C4 -137.95(11) . . . . ?
F1 C2 C3 C8 45.26(13) . . . . ?
F2 C2 C3 C4 -22.27(15) . . . . ?
F2 C2 C3 C8 160.94(10) . . . . ?
O1 C1 C2 F1 134.86(11) . . . . ?
O1 C1 C2 F2 20.91(14) . . . . ?
O1 C1 C2 C3 -101.92(12) . . . . ?
N1 N2 N3 C10 0.18(14) . . . . ?
N1 N2 N3 C13 -175.15(8) . . . . ?
N1 C1 C2 F1 -47.42(12) . . . . ?
N1 C1 C2 F2 -161.37(9) . . . . ?
N1 C1 C2 C3 75.80(11) . . . . ?
N2 N1 C1 O1 6.16(16) . . . . ?
N2 N1 C1 C2 -171.28(8) . . . . ?
N2 N3 C10 C11 -103.47(12) . . . . ?
N2 N3 C10 C12 130.91(11) . . . . ?
N2 N3 C13 C14 -73.44(13) . . . . ?
N2 N3 C13 C15 52.05(13) . . . . ?
C1 N1 N2 N3 -179.50(8) . . . . ?
C1 C2 C3 C4 99.21(12) . . . . ?
C1 C2 C3 C8 -77.58(13) . . . . ?
C2 C3 C4 C5 -177.90(11) . . . . ?
C2 C3 C8 C7 178.22(10) . . . . ?
C3 C4 C5 C6 -0.01(19) . . . . ?
C4 C3 C8 C7 1.37(17) . . . . ?
C4 C5 C6 C7 0.87(19) . . . . ?
C4 C5 C6 C9 -178.94(12) . . . . ?
C5 C6 C7 C8 -0.61(18) . . . . ?
C6 C7 C8 C3 -0.50(18) . . . . ?
C8 C3 C4 C5 -1.12(17) . . . . ?
C9 C6 C7 C8 179.19(12) . . . . ?
C10 N3 C13 C14 111.07(13) . . . . ?
C10 N3 C13 C15 -123.44(12) . . . . ?
C13 N3 C10 C11 71.60(13) . . . . ?
C13 N3 C10 C12 -54.02(14) . . . . ?
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
2.0005 -0.9968 -2.0000 -0.3961 -0.0758 -0.0724
-2.0005 0.9968 2.0000 0.3961 0.0758 0.0724
0.9991 0.0008 0.0006 -0.0769 -0.0944 0.1412
-0.9982 -1.0007 0.9982 0.0561 0.2431 -0.0157
0.9982 1.0007 -0.9982 -0.0561 -0.2431 0.0157
0.0014 -0.9994 -0.0012 -0.0946 0.1368 -0.0346
-0.0014 0.9994 0.0012 0.0946 -0.1368 0.0346
-0.9987 -1.0011 1.9982 0.1300 0.2550 0.1445
-4.9933 -3.0041 3.9934 0.3960 0.9300 -0.1693
0.0023 -1.9993 0.9977 -0.1153 0.2856 0.0910
1.0018 -1.9980 -0.0017 -0.2661 0.1793 0.0721
-0.0004 1.0003 -1.9989 -0.0531 -0.1607 -0.2857
