#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:23:09 +0300 (Mon, 06 Oct 2025) $
#$Revision: 302564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/08/7250802.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_7250802
loop_
_publ_author_name
'Ozeryanskii, Valery A.'
'Demidov, Oleg P.'
'Marchenko, Andrey V.'
_publ_section_title
;
 Intramolecular hydrogen bonding in 1,8-bis(dimethylamino)naphthalenes
 containing two to four heteroatomic functions in the ortho- and
 peri-positions: from CD3 to sulfur and selenium
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              6163
_journal_page_last               6173
_journal_paper_doi               10.1039/D5CE00621J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'B F4, C16 H22 D N2'
_chemical_formula_sum            'C16 H22 B D F4 N2'
_chemical_formula_weight         331.18
_chemical_name_common
'2-Methoxy-1,8-bis(dimethylamino)naphthalene hydrogen tetrafluoroborate'
_chemical_temperature_decomposition 501.6(5)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.15330(10)
_cell_length_b                   13.3033(2)
_cell_length_c                   17.4216(2)
_cell_measurement_reflns_used    6632
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.1240
_cell_measurement_theta_min      4.1460
_cell_volume                     1657.88(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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   -115.00 -64.00   1.00    1.00    --  -42.10-139.00 -55.00   51
  2  ω     33.00 150.00   1.00    3.19    --  112.00 -21.00 168.00  117
  3  ω     39.00 121.00   1.00    3.19    --  112.00-130.00 118.00   82
  4  ω    101.00 178.00   1.00    3.19    --  112.00 104.00 114.00   77
  5  ω   -121.00  -5.00   1.00    1.00    --  -42.10 -21.00 168.00  116
  6  ω   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00  90.00   98
  7  ω     23.00  98.00   1.00    1.00    --   42.10-125.00   0.00   75
  8  ω     36.00 113.00   1.00    3.19    --  112.00-111.00   0.00   77
  9  ω     86.00 171.00   1.00    3.19    --  112.00  45.00  30.00   85
 10  ω    139.00 165.00   1.00    3.19    --  112.00 111.00-120.00   26
 11  ω     81.00 122.00   1.00    3.19    --  112.00 -30.00-150.00   41
 12  ω     40.00  89.00   1.00    3.19    --  112.00-111.00 -60.00   49
 13  ω     36.00 113.00   1.00    3.19    --  112.00-111.00-150.00   77
 14  ω    115.00 142.00   1.00    3.19    --  112.00 111.00-150.00   27
 15  ω     88.00 113.00   1.00    3.19    --  112.00-111.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0191774000
_diffrn_orient_matrix_UB_12      -0.1045532000
_diffrn_orient_matrix_UB_13      -0.0371890000
_diffrn_orient_matrix_UB_21      0.0554446000
_diffrn_orient_matrix_UB_22      0.0496456000
_diffrn_orient_matrix_UB_23      -0.0765642000
_diffrn_orient_matrix_UB_31      0.2072105000
_diffrn_orient_matrix_UB_32      -0.0036074000
_diffrn_orient_matrix_UB_33      0.0239952000
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10264
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.234
_diffrn_reflns_theta_min         4.181
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.327
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CD3OD'
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0303
_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)+(0.0487P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                3226
_reflns_number_total             3369
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_21xDBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition' since the value had been given
as '228-229 deg.C (decomp.)'. The value was changed to '501.6(5)' --
it was converted from degrees Celsius (C) to kelvins (K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7250802--7250812.cif.
;
_cod_database_code               7250802
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C16 H22 B D F4 N2'
_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   0.931
_shelx_estimated_absorpt_t_min   0.677
_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. Restrained distances
 F2-B1 \\sim F2A-B1
 with sigma of 0.02
 F1-B1 \\sim F1A-B1
 with sigma of 0.02
 F4-B1 \\sim F4A-B1
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F3, F2, F1, F4, B1, F2A, F1A, F4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F2A)=Sof(F1A)=Sof(F4A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C7(H7)
5.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.762
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
F3 F 0.79151(15) 0.74610(8) 0.36447(8) 0.0305(3) Uani 1 1 d . . . . .
F2 F 1.098(2) 0.692(2) 0.362(2) 0.035(4) Uani 0.39(7) 1 d D . P A 1
F1 F 0.867(5) 0.5875(18) 0.3917(16) 0.037(3) Uani 0.39(7) 1 d D . P A 1
F4 F 0.923(4) 0.637(2) 0.2715(11) 0.045(3) Uani 0.39(7) 1 d D . P A 1
N2 N 0.38405(18) 0.46377(11) 0.34997(8) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.38980(19) 0.54319(11) 0.48370(8) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.5355(2) 0.47169(12) 0.50773(10) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.5423(2) 0.40025(12) 0.37035(10) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.6078(2) 0.40588(12) 0.44876(9) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.8237(2) 0.34024(13) 0.54686(11) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.923344 0.296614 0.560689 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7562(2) 0.34008(12) 0.47050(10) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.8353(2) 0.27391(12) 0.41566(12) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.934076 0.230259 0.430435 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6013(2) 0.46932(13) 0.58232(10) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.7480(3) 0.40200(13) 0.60068(10) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.794423 0.399950 0.651737 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6224(2) 0.33473(13) 0.31822(10) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.4184(3) 0.54056(14) 0.29035(11) 0.0239(4) Uani 1 1 d . . . . .
H16A H 0.544595 0.568028 0.296566 0.036 Uiso 1 1 calc R U . . .
H16B H 0.326495 0.594783 0.295488 0.036 Uiso 1 1 calc R U . . .
H16C H 0.406824 0.509803 0.239458 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4590(3) 0.64931(12) 0.47805(11) 0.0212(4) Uani 1 1 d . . . . .
H14A H 0.488741 0.674477 0.529487 0.032 Uiso 1 1 calc R U . . .
H14B H 0.361987 0.691582 0.454930 0.032 Uiso 1 1 calc R U . . .
H14C H 0.571624 0.651225 0.446033 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7716(2) 0.27214(13) 0.34216(11) 0.0227(4) Uani 1 1 d . . . . .
H7 H 0.828338 0.228063 0.306123 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5540(3) 0.32263(15) 0.23471(11) 0.0279(4) Uani 1 1 d . . . . .
H11A H 0.432421 0.288673 0.234463 0.042 Uiso 1 1 calc R U . . .
H11B H 0.644584 0.282479 0.205708 0.042 Uiso 1 1 calc R U . . .
H11C H 0.541580 0.389048 0.210916 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2067(2) 0.40807(14) 0.33925(12) 0.0247(4) Uani 1 1 d . . . . .
H15A H 0.212024 0.369919 0.291180 0.037 Uiso 1 1 calc R U . . .
H15B H 0.102342 0.455734 0.337177 0.037 Uiso 1 1 calc R U . . .
H15C H 0.188297 0.361700 0.382305 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2058(2) 0.53526(15) 0.52405(12) 0.0262(4) Uani 1 1 d . . . . .
H13A H 0.181728 0.464879 0.537401 0.039 Uiso 1 1 calc R U . . .
H13B H 0.106239 0.559794 0.490238 0.039 Uiso 1 1 calc R U . . .
H13C H 0.208804 0.575919 0.570942 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5248(3) 0.53263(15) 0.64774(11) 0.0287(4) Uani 1 1 d . . . . .
H12A H 0.515791 0.602912 0.631299 0.043 Uiso 1 1 calc R U . . .
H12B H 0.608706 0.527759 0.692038 0.043 Uiso 1 1 calc R U . . .
H12C H 0.400426 0.508049 0.662072 0.043 Uiso 1 1 calc R U . . .
B1 B 0.9130(3) 0.66824(15) 0.34545(12) 0.0197(4) Uani 1 1 d D . . . .
D2 D 0.369(4) 0.520(2) 0.4252(17) 0.046(8) Uiso 1 1 d . . . . .
F2A F 1.0915(15) 0.6958(13) 0.3701(13) 0.031(2) Uani 0.61(7) 1 d D . P A 2
F1A F 0.855(3) 0.5798(12) 0.3795(14) 0.042(3) Uani 0.61(7) 1 d D . P A 2
F4A F 0.898(2) 0.6610(17) 0.2655(5) 0.043(2) Uani 0.61(7) 1 d D . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 8 2 0.0513
0 -8 -2 0.0513
0 7 6 0.0456
1 -6 -8 0.0684
0 6 8 0.0439
0 -3 -10 0.0540
4 0 3 0.1995
0 1 11 0.0526
0 4 -10 0.0619
2 6 -6 0.1532
0 -6 8 0.0656
0 -9 1 0.0627
0 8 3 0.0575
-4 0 -3 0.2033
0 6 8 0.0403
0 6 9 0.0452
0 -6 -9 0.0350
0 3 10 0.0475
0 -2 11 0.0601
-1 2 -11 0.0604
4 -2 6 0.1725
1 -6 8 0.0791
-1 6 -8 0.0643
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
C9 N2 C16 116.33(13) . . ?
C9 N2 C15 113.96(13) . . ?
C9 N2 D2 97.7(11) . . ?
C16 N2 C15 113.56(14) . . ?
C16 N2 D2 106.1(11) . . ?
C15 N2 D2 107.1(11) . . ?
C1 N1 C14 113.16(13) . . ?
C1 N1 C13 116.35(14) . . ?
C1 N1 D2 100.7(16) . . ?
C14 N1 D2 104.6(16) . . ?
C13 N1 C14 112.82(14) . . ?
C13 N1 D2 107.5(16) . . ?
C10 C1 N1 116.27(14) . . ?
C2 C1 N1 121.55(15) . . ?
C2 C1 C10 122.17(15) . . ?
C10 C9 N2 116.90(14) . . ?
C8 C9 N2 121.84(15) . . ?
C8 C9 C10 121.23(15) . . ?
C1 C10 C9 125.91(15) . . ?
C5 C10 C1 116.68(15) . . ?
C5 C10 C9 117.40(15) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.87(15) . . ?
C4 C5 C10 120.17(15) . . ?
C4 C5 C6 119.89(15) . . ?
C6 C5 C10 119.94(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.80(15) . . ?
C7 C6 H6 119.6 . . ?
C1 C2 C3 118.62(16) . . ?
C1 C2 C12 124.74(16) . . ?
C3 C2 C12 116.63(16) . . ?
C4 C3 C2 121.47(16) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C9 C8 C7 119.30(16) . . ?
C9 C8 C11 123.61(16) . . ?
C7 C8 C11 117.06(16) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C7 C8 121.31(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3 B1 F2 112.1(13) . . ?
F3 B1 F2A 107.6(7) . . ?
F3 B1 F4A 104.0(10) . . ?
F1 B1 F3 107.0(15) . . ?
F1 B1 F2 106(2) . . ?
F4 B1 F3 119.2(15) . . ?
F4 B1 F2 102(2) . . ?
F4 B1 F1 109.2(16) . . ?
F2A B1 F4A 113.1(11) . . ?
F1A B1 F3 110.1(10) . . ?
F1A B1 F2A 111.4(13) . . ?
F1A B1 F4A 110.2(10) . . ?
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
F3 B1 1.392(2) . ?
F2 B1 1.392(14) . ?
F1 B1 1.382(15) . ?
F4 B1 1.356(13) . ?
N2 C9 1.456(2) . ?
N2 C16 1.477(2) . ?
N2 C15 1.481(2) . ?
N2 D2 1.52(3) . ?
N1 C1 1.472(2) . ?
N1 C14 1.499(2) . ?
N1 C13 1.496(2) . ?
N1 D2 1.07(3) . ?
C1 C10 1.446(2) . ?
C1 C2 1.382(2) . ?
C9 C10 1.446(2) . ?
C9 C8 1.383(2) . ?
C10 C5 1.427(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(2) . ?
C4 C3 1.359(3) . ?
C5 C6 1.417(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.359(3) . ?
C2 C3 1.416(3) . ?
C2 C12 1.519(3) . ?
C3 H3 0.9500 . ?
C8 C7 1.417(2) . ?
C8 C11 1.543(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C7 H7 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
B1 F2A 1.396(10) . ?
B1 F1A 1.381(9) . ?
B1 F4A 1.401(8) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C9 C10 C1 -2.7(2) . . . . ?
N2 C9 C10 C5 176.71(13) . . . . ?
N2 C9 C8 C7 -177.71(15) . . . . ?
N2 C9 C8 C11 0.1(3) . . . . ?
N1 C1 C10 C9 -3.9(2) . . . . ?
N1 C1 C10 C5 176.70(13) . . . . ?
N1 C1 C2 C3 -176.98(15) . . . . ?
N1 C1 C2 C12 4.4(3) . . . . ?
C1 C10 C5 C4 0.9(2) . . . . ?
C1 C10 C5 C6 -179.51(14) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C9 C10 C5 C4 -178.52(14) . . . . ?
C9 C10 C5 C6 1.1(2) . . . . ?
C9 C8 C7 C6 1.2(3) . . . . ?
C10 C1 C2 C3 1.8(2) . . . . ?
C10 C1 C2 C12 -176.79(16) . . . . ?
C10 C9 C8 C7 -0.1(2) . . . . ?
C10 C9 C8 C11 177.75(16) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C4 C5 C6 C7 179.58(16) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C2 C1 C10 C9 177.25(15) . . . . ?
C2 C1 C10 C5 -2.1(2) . . . . ?
C3 C4 C5 C10 0.6(2) . . . . ?
C3 C4 C5 C6 -178.99(16) . . . . ?
C8 C9 C10 C1 179.62(15) . . . . ?
C8 C9 C10 C5 -1.0(2) . . . . ?
C16 N2 C9 C10 117.87(16) . . . . ?
C16 N2 C9 C8 -64.4(2) . . . . ?
C14 N1 C1 C10 -106.29(16) . . . . ?
C14 N1 C1 C2 72.54(19) . . . . ?
C11 C8 C7 C6 -176.77(17) . . . . ?
C15 N2 C9 C10 -107.06(17) . . . . ?
C15 N2 C9 C8 70.6(2) . . . . ?
C13 N1 C1 C10 120.66(16) . . . . ?
C13 N1 C1 C2 -60.5(2) . . . . ?
C12 C2 C3 C4 178.50(17) . . . . ?
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
-0.0844 8.4415 2.3755 -0.9725 0.2325 0.0091
0.0844 -8.4415 -2.3755 0.9725 -0.2325 -0.0091
-0.4683 7.4757 5.5452 -0.9968 -0.0794 0.0091
0.8023 -5.7778 -8.1747 0.9235 0.3835 -0.0091
-0.4115 5.7295 8.4012 -0.9194 -0.3816 0.0957
0.2502 -3.4097 -10.3712 0.7470 0.6387 -0.1847
4.4786 -0.2574 2.9594 0.0027 0.0090 1.0000
-0.1982 0.8288 11.2454 -0.5087 -0.8308 0.2258
-0.3073 4.1694 -9.8739 -0.0746 0.9459 -0.3156
2.3522 5.9763 -5.8200 -0.3633 0.8727 0.3262
-0.1157 -6.3491 7.6603 0.3767 -0.9081 0.1827
-0.2305 -8.5857 1.0795 0.8531 -0.5217 0.0091
0.4257 8.3463 2.7101 -0.9653 0.2305 0.1231
-4.4627 0.1964 -3.1061 0.0094 0.0001 -1.0000
-0.2443 5.6919 8.4831 -0.9153 -0.3805 0.1324
0.2701 5.5370 8.6516 -0.8955 -0.3725 0.2436
-0.1044 -5.5948 -8.6093 0.9031 0.3756 -0.2080
0.1579 3.3068 10.4382 -0.7309 -0.6263 0.2712
0.1732 -1.7905 11.0537 -0.2206 -0.9256 0.3076
-0.6340 1.7542 -10.9628 0.2121 0.8913 -0.4007
3.9265 -1.5452 5.6804 0.0256 -0.2939 0.9555
0.9194 -5.9879 7.8331 0.3524 -0.8460 0.4001
-0.5154 6.1702 -7.8107 -0.3645 0.8758 -0.3165
