#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:14:38 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549414.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_1549414
loop_
_publ_author_name
'Shiro, Tomoya'
'Schuhmacher, Anne'
'Jackl, Moritz K.'
'Bode, Jeffrey W.'
_publ_section_title
;
Facile synthesis of \a-aminoboronic acids from amines and potassium
acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).
;
_journal_issue 23
_journal_name_full 'Chemical science'
_journal_page_first 5191
_journal_page_last 5196
_journal_paper_doi 10.1039/c8sc01486h
_journal_volume 9
_journal_year 2018
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C11 H12 B Br F3 N'
_chemical_formula_sum 'C11 H12 B Br F3 N'
_chemical_formula_weight 305.94
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_Hall 'P 2yb'
_space_group_name_H-M_alt 'P 1 21 1'
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_audit_creation_date 2016-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 90.442(3)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 9.1247(8)
_cell_length_b 11.1474(11)
_cell_length_c 11.9275(12)
_cell_measurement_reflns_used 9930
_cell_measurement_temperature 100.0(2)
_cell_measurement_theta_max 28.28
_cell_measurement_theta_min 2.50
_cell_volume 1213.2(2)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature 100.0(2)
_diffrn_detector 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'kappa-stage diffractometer'
_diffrn_measurement_device_type 'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator 'double mirror optics'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0261
_diffrn_reflns_av_unetI/netI 0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 22040
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 28.291
_diffrn_reflns_theta_min 2.501
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms high brilliance'
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 3.401
_exptl_absorpt_correction_T_max 0.7302
_exptl_absorpt_correction_T_min 0.5817
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.7966.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.675
_exptl_crystal_description plate
_exptl_crystal_F_000 608
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.343
_refine_diff_density_min -0.263
_refine_diff_density_rms 0.047
_refine_ls_abs_structure_details
;
Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.017(3)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.908
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 335
_refine_ls_number_reflns 5908
_refine_ls_number_restraints 136
_refine_ls_restrained_S_all 0.918
_refine_ls_R_factor_all 0.0219
_refine_ls_R_factor_gt 0.0191
_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/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0384
_refine_ls_wR_factor_ref 0.0389
_reflns_Friedel_coverage 0.871
_reflns_Friedel_fraction_full 0.967
_reflns_Friedel_fraction_max 0.962
_reflns_number_gt 5500
_reflns_number_total 5908
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file c8sc01486h1.cif
_cod_data_source_block jb080616_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1549414--1549418.cif.'
_cod_database_code 1549414
_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 0.905
_shelx_estimated_absorpt_t_min 0.535
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Restrained distances
F2-B1 \\sim F2A-B1 \\sim F3-B1 \\sim F3A-B1 \\sim F1-B1 \\sim F1A-B1
with sigma of 0.02
F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
with sigma of 0.02
3. Rigid bond restraints
F3, F2, F1, B1, F2A, F3A, F1A
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
F3, F2, F1, B1, F2A, F3A, F1A, C7
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
Sof(F3)=Sof(F2)=Sof(F1)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C19(H19A,H19B), C9(H9A,H9B), C22(H22A,H22B), C20(H20A,H20B),
C11(H11A,H11B), C10(H10A,H10B), C21(H21A,H21B)
7.b Aromatic/amide H refined with riding coordinates:
C5(H5), C13(H13), C6(H6), C17(H17), C14(H14), C3(H3), C16(H16), C2(H2)
;
_shelx_res_file
;
jb080616_1_1_0m.res created by SHELXL-2014/7
TITL jb080616_1_1_0m_a.res in P2(1)
REM Old TITL jb080616_1_1_0m in P21 #4
REM SHELXT solution in P2(1)
REM R1 0.080, Rweak 0.041, Alpha 0.002, Orientation as input
REM Flack x = 0.060 ( 0.004 ) from Parsons' quotients
REM Formula found by SHELXT: C24 N2 F6 Br2
CELL 0.71073 9.1247 11.1474 11.9275 90 90.442 90
ZERR 4 0.0008 0.0011 0.0012 0 0.003 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H B Br F N
UNIT 44 48 4 4 12 4
SADI F2 B1 F2A B1 F3 B1 F3A B1 F1 B1 F1A B1
SADI F1 F2 F2 F3 F3 F1 F1A F2A F2A F3A F3A F1A
DELU F3 F2 F1 B1 F2A F3A F1A
RIGU F3 F2 F1 B1 F2A F3A F1A C7
ISOR 0.005 0.01 F1 F1A F2 F2A F3 F3A
L.S. 20
PLAN 5
SIZE 0.03 0.19 0.21
TEMP -173.1(2)
BOND $H
MORE -1
CONF
fmap 2
acta 52
OMIT 0 0 1
OMIT 0 1 1
OMIT 1 0 0
REM
REM
REM
WGHT 0.000000
FVAR 0.57280 0.37624
BR1 4 0.349752 -0.040693 0.913281 11.00000 0.03022 0.01521 =
0.02288 0.00345 -0.00202 0.00736
BR2 4 0.111870 0.499713 0.091253 11.00000 0.03009 0.02727 =
0.01929 -0.01045 -0.00284 -0.00163
F6 5 0.211438 1.041474 0.520519 11.00000 0.02589 0.01189 =
0.02667 -0.00057 0.00230 0.00255
F4 5 0.044781 0.910499 0.446809 11.00000 0.01709 0.02868 =
0.02314 -0.00782 -0.00413 0.00752
F5 5 0.127706 0.885685 0.626688 11.00000 0.02359 0.01901 =
0.01780 0.00262 0.00650 0.00707
PART 1
F3 5 0.321769 0.653392 0.666822 21.00000 0.01711 0.02347 =
0.03256 0.00956 0.00295 0.00258
F2 5 0.421256 0.625038 0.840488 21.00000 0.02768 0.04950 =
0.03091 0.00525 -0.00725 -0.02140
F1 5 0.467013 0.492381 0.699718 21.00000 0.02040 0.02056 =
0.05594 0.01316 0.01536 0.00560
PART 0
N2 6 0.431572 0.840466 0.515790 11.00000 0.01620 0.01107 =
0.01673 -0.00226 0.00254 -0.00071
N1 6 0.086610 0.523489 0.782384 11.00000 0.01332 0.01204 =
0.01506 0.00163 -0.00078 -0.00027
C5 1 0.191616 0.260738 0.749323 11.00000 0.01335 0.01499 =
0.01294 0.00149 -0.00096 0.00071
AFIX 43
H5 2 0.132131 0.276647 0.685317 11.00000 -1.20000
AFIX 0
C18 1 0.302021 0.836088 0.472531 11.00000 0.01561 0.00887 =
0.01299 0.00260 0.00221 -0.00151
C15 1 0.271101 0.749772 0.380757 11.00000 0.01014 0.01118 =
0.01553 -0.00088 0.00109 0.00304
C4 1 0.246261 0.355430 0.813489 11.00000 0.01036 0.01258 =
0.01566 0.00009 0.00265 0.00040
C13 1 0.126424 0.581711 0.315939 11.00000 0.01229 0.01426 =
0.01900 -0.00011 0.00048 -0.00216
AFIX 43
H13 2 0.060447 0.517735 0.330426 11.00000 -1.20000
AFIX 0
C8 1 -0.048581 0.454057 0.811591 11.00000 0.01167 0.02029 =
0.01577 0.00099 0.00076 -0.00444
AFIX 23
H8A 2 -0.042478 0.423150 0.889299 11.00000 -1.20000
H8B 2 -0.062913 0.385720 0.759642 11.00000 -1.20000
AFIX 0
C6 1 0.224249 0.142481 0.779059 11.00000 0.01572 0.01560 =
0.01555 -0.00225 0.00089 0.00085
AFIX 43
H6 2 0.188851 0.077487 0.735024 11.00000 -1.20000
AFIX 0
C12 1 0.180406 0.599942 0.209141 11.00000 0.01476 0.01431 =
0.01374 -0.00407 -0.00274 0.00503
C19 1 0.558363 0.762286 0.484798 11.00000 0.01239 0.02058 =
0.02726 -0.00755 0.00280 0.00250
AFIX 23
H19A 2 0.582736 0.771630 0.404535 11.00000 -1.20000
H19B 2 0.536438 0.676856 0.499936 11.00000 -1.20000
AFIX 0
C17 1 0.281696 0.688877 0.186144 11.00000 0.01677 0.01987 =
0.01364 -0.00084 0.00469 0.00296
AFIX 43
H17 2 0.318442 0.698913 0.112431 11.00000 -1.20000
AFIX 0
C14 1 0.170139 0.658219 0.401301 11.00000 0.01284 0.01761 =
0.01251 0.00043 0.00231 0.00005
AFIX 43
H14 2 0.131227 0.648420 0.474377 11.00000 -1.20000
AFIX 0
C3 1 0.335137 0.331438 0.906739 11.00000 0.01131 0.01574 =
0.01728 -0.00435 0.00077 -0.00078
AFIX 43
H3 2 0.376026 0.396064 0.948420 11.00000 -1.20000
AFIX 0
C9 1 -0.172487 0.544726 0.799415 11.00000 0.01552 0.02837 =
0.02628 -0.00110 0.00108 0.00423
AFIX 23
H9A 2 -0.215669 0.542061 0.723056 11.00000 -1.20000
H9B 2 -0.250523 0.529213 0.854769 11.00000 -1.20000
AFIX 0
C22 1 0.472235 0.914818 0.614694 11.00000 0.02147 0.01678 =
0.02255 -0.00743 -0.00561 0.00110
AFIX 23
H22A 2 0.390904 0.918355 0.669054 11.00000 -1.20000
H22B 2 0.498101 0.997456 0.591766 11.00000 -1.20000
AFIX 0
C7 1 0.219524 0.483899 0.782689 11.00000 0.01431 0.01663 =
0.01377 -0.00124 -0.00187 0.00169
C16 1 0.328704 0.763238 0.272774 11.00000 0.01572 0.01350 =
0.01867 -0.00058 0.00336 -0.00118
AFIX 43
H16 2 0.400057 0.823364 0.258819 11.00000 -1.20000
AFIX 0
C2 1 0.364280 0.214388 0.939079 11.00000 0.01167 0.02012 =
0.01311 0.00119 -0.00091 0.00296
AFIX 43
H2 2 0.420831 0.198005 1.004512 11.00000 -1.20000
AFIX 0
C20 1 0.683800 0.806794 0.559571 11.00000 0.01489 0.02271 =
0.03491 -0.00740 -0.00090 -0.00065
AFIX 23
H20A 2 0.738075 0.872993 0.523320 11.00000 -1.20000
H20B 2 0.752939 0.741100 0.577929 11.00000 -1.20000
AFIX 0
C11 1 0.046082 0.651666 0.760900 11.00000 0.01888 0.01520 =
0.02812 0.00494 0.00013 0.00312
AFIX 23
H11A 2 0.034571 0.667474 0.679632 11.00000 -1.20000
H11B 2 0.120634 0.707000 0.792360 11.00000 -1.20000
AFIX 0
C10 1 -0.099183 0.664294 0.821353 11.00000 0.02189 0.01937 =
0.02931 -0.00119 0.00157 0.00703
AFIX 23
H10A 2 -0.083872 0.677739 0.902648 11.00000 -1.20000
H10B 2 -0.157854 0.731232 0.790006 11.00000 -1.20000
AFIX 0
C21 1 0.603758 0.850587 0.664405 11.00000 0.01804 0.01607 =
0.02573 -0.00389 -0.00460 -0.00130
AFIX 23
H21A 2 0.573404 0.782552 0.712257 11.00000 -1.20000
H21B 2 0.665754 0.905974 0.709048 11.00000 -1.20000
AFIX 0
C1 1 0.308931 0.121623 0.873653 11.00000 0.01609 0.01063 =
0.01464 0.00069 0.00394 0.00417
B1 3 0.360722 0.570128 0.750763 11.00000 0.01372 0.01639 =
0.04080 0.01023 -0.00161 -0.00271
B2 3 0.165700 0.922052 0.518731 11.00000 0.01686 0.01453 =
0.01638 -0.00206 -0.00010 0.00478
PART 2
F2A 5 0.382009 0.648922 0.844500 -21.00000 0.02360 0.02862 =
0.04798 0.00427 -0.01571 -0.01403
F3A 5 0.329643 0.635706 0.655684 -21.00000 0.02168 0.03100 =
0.03535 0.01316 0.00629 -0.00418
F1A 5 0.483508 0.501366 0.738071 -21.00000 0.01217 0.02436 =
0.10071 0.01966 0.00700 -0.00016
HKLF 4
REM jb080616_1_1_0m_a.res in P2(1)
REM R1 = 0.0191 for 5500 Fo > 4sig(Fo) and 0.0219 for all 5908 data
REM 335 parameters refined using 136 restraints
END
WGHT 0.0000 0.0000
REM Highest difference peak 0.343, deepest hole -0.263, 1-sigma level 0.047
Q1 1 0.1259 0.4971 0.0083 11.00000 0.05 0.34
Q2 1 0.3371 -0.0392 0.9976 11.00000 0.05 0.32
Q3 1 0.3633 -0.0413 0.8366 11.00000 0.05 0.30
Q4 1 0.1007 0.5003 0.1682 11.00000 0.05 0.29
Q5 1 0.2759 0.5330 0.7686 11.00000 0.05 0.28
;
_shelx_res_checksum 25105
_shelx_shelxl_version_number 2014/7
_olex2_date_sample_data_collection 2016-06-08
_olex2_date_sample_submission 2016-06-07
_olex2_submission_original_sample_id jb080616_1_1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
Br1 Br 0.34975(3) -0.04069(2) 0.91328(2) 0.02278(7) Uani 1 1 d . . . . .
Br2 Br 0.11187(3) 0.49971(2) 0.09125(2) 0.02557(7) Uani 1 1 d . . . . .
F6 F 0.21144(15) 1.04147(12) 0.52052(12) 0.0215(3) Uani 1 1 d . . . . .
F4 F 0.04478(14) 0.91050(13) 0.44681(12) 0.0230(3) Uani 1 1 d . . . . .
F5 F 0.12771(15) 0.88569(13) 0.62669(12) 0.0201(3) Uani 1 1 d . . . . .
F3 F 0.322(4) 0.653(2) 0.6668(18) 0.024(3) Uani 0.38(4) 1 d D U P A 1
F2 F 0.421(3) 0.625(2) 0.8405(10) 0.036(3) Uani 0.38(4) 1 d D U P A 1
F1 F 0.467(2) 0.4924(14) 0.6997(16) 0.032(3) Uani 0.38(4) 1 d D U P A 1
N2 N 0.4316(2) 0.84047(17) 0.51579(17) 0.0147(4) Uani 1 1 d . . . . .
N1 N 0.08661(19) 0.52349(17) 0.78238(16) 0.0135(4) Uani 1 1 d . . . . .
C5 C 0.1916(2) 0.2607(2) 0.7493(2) 0.0138(5) Uani 1 1 d . . . . .
H5 H 0.1321 0.2766 0.6853 0.017 Uiso 1 1 calc R . . . .
C18 C 0.3020(2) 0.8361(2) 0.47253(19) 0.0125(5) Uani 1 1 d . . . . .
C15 C 0.2711(2) 0.7498(2) 0.3808(2) 0.0123(5) Uani 1 1 d . . . . .
C4 C 0.2463(2) 0.3554(2) 0.8135(2) 0.0129(5) Uani 1 1 d . . . . .
C13 C 0.1264(2) 0.5817(2) 0.3159(2) 0.0152(5) Uani 1 1 d . . . . .
H13 H 0.0604 0.5177 0.3304 0.018 Uiso 1 1 calc R . . . .
C8 C -0.0486(2) 0.4541(2) 0.81159(19) 0.0159(5) Uani 1 1 d . . . . .
H8A H -0.0425 0.4231 0.8893 0.019 Uiso 1 1 calc R . . . .
H8B H -0.0629 0.3857 0.7596 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2242(2) 0.1425(2) 0.7791(2) 0.0156(5) Uani 1 1 d . . . . .
H6 H 0.1889 0.0775 0.7350 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1804(2) 0.5999(2) 0.2091(2) 0.0143(5) Uani 1 1 d . . . . .
C19 C 0.5584(2) 0.7623(2) 0.4848(2) 0.0201(6) Uani 1 1 d . . . . .
H19A H 0.5827 0.7716 0.4045 0.024 Uiso 1 1 calc R . . . .
H19B H 0.5364 0.6769 0.4999 0.024 Uiso 1 1 calc R . . . .
C17 C 0.2817(2) 0.6889(2) 0.1861(2) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.3184 0.6989 0.1124 0.020 Uiso 1 1 calc R . . . .
C14 C 0.1701(2) 0.6582(2) 0.4013(2) 0.0143(5) Uani 1 1 d . . . . .
H14 H 0.1312 0.6484 0.4744 0.017 Uiso 1 1 calc R . . . .
C3 C 0.3351(2) 0.3314(2) 0.9067(2) 0.0148(5) Uani 1 1 d . . . . .
H3 H 0.3760 0.3961 0.9484 0.018 Uiso 1 1 calc R . . . .
C9 C -0.1725(3) 0.5447(2) 0.7994(2) 0.0234(6) Uani 1 1 d . . . . .
H9A H -0.2157 0.5421 0.7231 0.028 Uiso 1 1 calc R . . . .
H9B H -0.2505 0.5292 0.8548 0.028 Uiso 1 1 calc R . . . .
C22 C 0.4722(3) 0.9148(2) 0.6147(2) 0.0203(6) Uani 1 1 d . . . . .
H22A H 0.3909 0.9184 0.6691 0.024 Uiso 1 1 calc R . . . .
H22B H 0.4981 0.9975 0.5918 0.024 Uiso 1 1 calc R . . . .
C7 C 0.2195(2) 0.4839(2) 0.78269(18) 0.0149(5) Uani 1 1 d . U . . .
C16 C 0.3287(3) 0.7632(2) 0.2728(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.4001 0.8234 0.2588 0.019 Uiso 1 1 calc R . . . .
C2 C 0.3643(2) 0.2144(2) 0.9391(2) 0.0150(5) Uani 1 1 d . . . . .
H2 H 0.4208 0.1980 1.0045 0.018 Uiso 1 1 calc R . . . .
C20 C 0.6838(3) 0.8068(2) 0.5596(2) 0.0242(6) Uani 1 1 d . . . . .
H20A H 0.7381 0.8730 0.5233 0.029 Uiso 1 1 calc R . . . .
H20B H 0.7529 0.7411 0.5779 0.029 Uiso 1 1 calc R . . . .
C11 C 0.0461(3) 0.6517(2) 0.7609(2) 0.0207(5) Uani 1 1 d . . . . .
H11A H 0.0346 0.6675 0.6796 0.025 Uiso 1 1 calc R . . . .
H11B H 0.1206 0.7070 0.7924 0.025 Uiso 1 1 calc R . . . .
C10 C -0.0992(3) 0.6643(2) 0.8214(2) 0.0235(6) Uani 1 1 d . . . . .
H10A H -0.0839 0.6777 0.9026 0.028 Uiso 1 1 calc R . . . .
H10B H -0.1579 0.7312 0.7900 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6038(3) 0.8506(2) 0.6644(2) 0.0200(6) Uani 1 1 d . . . . .
H21A H 0.5734 0.7826 0.7123 0.024 Uiso 1 1 calc R . . . .
H21B H 0.6658 0.9060 0.7090 0.024 Uiso 1 1 calc R . . . .
C1 C 0.3089(2) 0.1216(2) 0.8737(2) 0.0138(5) Uani 1 1 d . . . . .
B1 B 0.3607(3) 0.5701(3) 0.7508(3) 0.0236(7) Uani 1 1 d D U . . .
B2 B 0.1657(3) 0.9221(3) 0.5187(2) 0.0159(6) Uani 1 1 d . . . . .
F2A F 0.3820(15) 0.6489(9) 0.8445(7) 0.0335(16) Uani 0.62(4) 1 d D U P A 2
F3A F 0.330(2) 0.6357(14) 0.6557(9) 0.029(2) Uani 0.62(4) 1 d D U P A 2
F1A F 0.4835(9) 0.5014(9) 0.7381(19) 0.046(2) Uani 0.62(4) 1 d D U P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03022(13) 0.01521(13) 0.02288(14) 0.00345(11) -0.00202(10) 0.00736(11)
Br2 0.03009(13) 0.02727(15) 0.01929(14) -0.01045(11) -0.00284(10) -0.00163(11)
F6 0.0259(8) 0.0119(7) 0.0267(9) -0.0006(6) 0.0023(6) 0.0026(6)
F4 0.0171(7) 0.0287(8) 0.0231(8) -0.0078(7) -0.0041(6) 0.0075(6)
F5 0.0236(7) 0.0190(8) 0.0178(8) 0.0026(6) 0.0065(6) 0.0071(6)
F3 0.017(4) 0.023(5) 0.033(5) 0.010(4) 0.003(4) 0.003(3)
F2 0.028(6) 0.049(6) 0.031(3) 0.005(3) -0.007(3) -0.021(4)
F1 0.020(4) 0.021(3) 0.056(6) 0.013(4) 0.015(4) 0.006(3)
N2 0.0162(10) 0.0111(10) 0.0167(11) -0.0023(8) 0.0025(8) -0.0007(8)
N1 0.0133(9) 0.0120(11) 0.0151(10) 0.0016(8) -0.0008(8) -0.0003(7)
C5 0.0133(11) 0.0150(12) 0.0129(13) 0.0015(10) -0.0010(9) 0.0007(9)
C18 0.0156(11) 0.0089(11) 0.0130(12) 0.0026(9) 0.0022(9) -0.0015(8)
C15 0.0101(10) 0.0112(12) 0.0155(13) -0.0009(9) 0.0011(9) 0.0030(8)
C4 0.0104(10) 0.0126(12) 0.0157(12) 0.0001(10) 0.0026(9) 0.0004(9)
C13 0.0123(11) 0.0143(12) 0.0190(13) -0.0001(10) 0.0005(9) -0.0022(9)
C8 0.0117(10) 0.0203(12) 0.0158(12) 0.0010(11) 0.0008(9) -0.0044(10)
C6 0.0157(11) 0.0156(12) 0.0156(13) -0.0022(10) 0.0009(10) 0.0008(9)
C12 0.0148(11) 0.0143(12) 0.0137(12) -0.0041(10) -0.0027(9) 0.0050(9)
C19 0.0124(11) 0.0206(14) 0.0273(16) -0.0075(12) 0.0028(11) 0.0025(10)
C17 0.0168(11) 0.0199(13) 0.0136(13) -0.0008(10) 0.0047(10) 0.0030(10)
C14 0.0128(10) 0.0176(13) 0.0125(12) 0.0004(10) 0.0023(9) 0.0000(9)
C3 0.0113(11) 0.0157(13) 0.0173(13) -0.0043(10) 0.0008(10) -0.0008(9)
C9 0.0155(12) 0.0284(15) 0.0263(15) -0.0011(12) 0.0011(11) 0.0042(11)
C22 0.0215(12) 0.0168(12) 0.0226(14) -0.0074(11) -0.0056(11) 0.0011(10)
C7 0.0143(10) 0.0166(14) 0.0138(11) -0.0012(10) -0.0019(8) 0.0017(9)
C16 0.0157(11) 0.0135(12) 0.0187(14) -0.0006(10) 0.0034(10) -0.0012(9)
C2 0.0117(11) 0.0201(13) 0.0131(13) 0.0012(10) -0.0009(9) 0.0030(9)
C20 0.0149(12) 0.0227(15) 0.0349(17) -0.0074(12) -0.0009(11) -0.0007(10)
C11 0.0189(12) 0.0152(12) 0.0281(15) 0.0049(11) 0.0001(11) 0.0031(10)
C10 0.0219(13) 0.0194(14) 0.0293(16) -0.0012(12) 0.0016(11) 0.0070(11)
C21 0.0180(12) 0.0161(13) 0.0257(15) -0.0039(11) -0.0046(11) -0.0013(10)
C1 0.0161(11) 0.0106(12) 0.0146(13) 0.0007(9) 0.0039(9) 0.0042(9)
B1 0.0137(13) 0.0164(15) 0.0408(19) 0.0102(13) -0.0016(12) -0.0027(11)
B2 0.0169(13) 0.0145(13) 0.0164(15) -0.0021(11) -0.0001(11) 0.0048(10)
F2A 0.024(4) 0.029(3) 0.048(2) 0.0043(17) -0.016(2) -0.014(2)
F3A 0.022(3) 0.031(4) 0.035(3) 0.013(3) 0.006(2) -0.004(3)
F1A 0.0122(17) 0.024(2) 0.101(7) 0.020(4) 0.007(3) -0.0002(16)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 N2 C19 126.0(2)
C18 N2 C22 124.21(19)
C22 N2 C19 109.38(17)
C7 N1 C8 126.7(2)
C7 N1 C11 123.9(2)
C11 N1 C8 109.25(18)
C4 C5 H5 120.0
C4 C5 C6 120.0(2)
C6 C5 H5 120.0
N2 C18 C15 119.3(2)
N2 C18 B2 122.1(2)
C15 C18 B2 118.60(19)
C14 C15 C18 117.8(2)
C14 C15 C16 119.4(2)
C16 C15 C18 122.5(2)
C5 C4 C3 119.7(2)
C5 C4 C7 122.2(2)
C3 C4 C7 118.1(2)
C12 C13 H13 120.5
C12 C13 C14 118.9(2)
C14 C13 H13 120.5
N1 C8 H8A 110.9
N1 C8 H8B 110.9
N1 C8 C9 104.3(2)
H8A C8 H8B 108.9
C9 C8 H8A 110.9
C9 C8 H8B 110.9
C5 C6 H6 120.6
C1 C6 C5 118.9(2)
C1 C6 H6 120.6
C13 C12 Br2 118.54(18)
C17 C12 Br2 119.43(18)
C17 C12 C13 122.0(2)
N2 C19 H19A 110.9
N2 C19 H19B 110.9
N2 C19 C20 104.10(19)
H19A C19 H19B 109.0
C20 C19 H19A 110.9
C20 C19 H19B 110.9
C12 C17 H17 120.6
C12 C17 C16 118.8(2)
C16 C17 H17 120.6
C15 C14 H14 119.8
C13 C14 C15 120.5(2)
C13 C14 H14 119.8
C4 C3 H3 119.6
C2 C3 C4 120.7(2)
C2 C3 H3 119.6
C8 C9 H9A 111.0
C8 C9 H9B 111.0
H9A C9 H9B 109.0
C10 C9 C8 103.96(19)
C10 C9 H9A 111.0
C10 C9 H9B 111.0
N2 C22 H22A 111.0
N2 C22 H22B 111.0
N2 C22 C21 103.85(19)
H22A C22 H22B 109.0
C21 C22 H22A 111.0
C21 C22 H22B 111.0
N1 C7 C4 118.6(2)
N1 C7 B1 122.3(2)
C4 C7 B1 119.10(18)
C15 C16 H16 119.9
C17 C16 C15 120.2(2)
C17 C16 H16 119.9
C3 C2 H2 120.8
C3 C2 C1 118.5(2)
C1 C2 H2 120.8
C19 C20 H20A 111.2
C19 C20 H20B 111.2
C19 C20 C21 102.71(19)
H20A C20 H20B 109.1
C21 C20 H20A 111.2
C21 C20 H20B 111.2
N1 C11 H11A 111.2
N1 C11 H11B 111.2
N1 C11 C10 102.84(19)
H11A C11 H11B 109.1
C10 C11 H11A 111.2
C10 C11 H11B 111.2
C9 C10 C11 102.8(2)
C9 C10 H10A 111.2
C9 C10 H10B 111.2
C11 C10 H10A 111.2
C11 C10 H10B 111.2
H10A C10 H10B 109.1
C22 C21 C20 102.3(2)
C22 C21 H21A 111.3
C22 C21 H21B 111.3
C20 C21 H21A 111.3
C20 C21 H21B 111.3
H21A C21 H21B 109.2
C6 C1 Br1 117.97(18)
C6 C1 C2 122.2(2)
C2 C1 Br1 119.88(18)
F3 B1 F1 105.3(11)
F3 B1 C7 110.7(15)
F2 B1 F3 111.4(12)
F2 B1 F1 109.6(7)
F2 B1 C7 113.3(7)
F1 B1 C7 106.0(8)
F2A B1 C7 106.1(5)
F3A B1 C7 110.0(9)
F3A B1 F2A 110.0(7)
F1A B1 C7 109.9(5)
F1A B1 F2A 108.9(5)
F1A B1 F3A 111.7(9)
F6 B2 F4 109.4(2)
F6 B2 F5 109.8(2)
F6 B2 C18 109.24(19)
F4 B2 C18 109.4(2)
F5 B2 F4 109.8(2)
F5 B2 C18 109.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.906(2)
Br2 C12 1.898(2)
F6 B2 1.395(3)
F4 B2 1.398(3)
F5 B2 1.396(3)
F3 B1 1.409(14)
F2 B1 1.348(11)
F1 B1 1.439(10)
N2 C18 1.287(3)
N2 C19 1.497(3)
N2 C22 1.486(3)
N1 C8 1.500(3)
N1 C7 1.291(3)
N1 C11 1.498(3)
C5 H5 0.9500
C5 C4 1.394(3)
C5 C6 1.397(3)
C18 C15 1.483(3)
C18 B2 1.667(3)
C15 C14 1.398(3)
C15 C16 1.403(3)
C4 C3 1.397(3)
C4 C7 1.498(3)
C13 H13 0.9500
C13 C12 1.384(3)
C13 C14 1.384(3)
C8 H8A 0.9900
C8 H8B 0.9900
C8 C9 1.523(3)
C6 H6 0.9500
C6 C1 1.382(3)
C12 C17 1.384(3)
C19 H19A 0.9900
C19 H19B 0.9900
C19 C20 1.528(3)
C17 H17 0.9500
C17 C16 1.390(3)
C14 H14 0.9500
C3 H3 0.9500
C3 C2 1.386(3)
C9 H9A 0.9900
C9 H9B 0.9900
C9 C10 1.513(4)
C22 H22A 0.9900
C22 H22B 0.9900
C22 C21 1.514(3)
C7 B1 1.654(3)
C16 H16 0.9500
C2 H2 0.9500
C2 C1 1.388(3)
C20 H20A 0.9900
C20 H20B 0.9900
C20 C21 1.533(4)
C11 H11A 0.9900
C11 H11B 0.9900
C11 C10 1.520(3)
C10 H10A 0.9900
C10 H10B 0.9900
C21 H21A 0.9900
C21 H21B 0.9900
B1 F2A 1.434(8)
B1 F3A 1.377(9)
B1 F1A 1.367(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
Br2 C12 C17 C16 178.69(17)
N2 C18 C15 C14 115.6(2)
N2 C18 C15 C16 -70.2(3)
N2 C18 B2 F6 52.1(3)
N2 C18 B2 F4 171.8(2)
N2 C18 B2 F5 -68.0(3)
N2 C19 C20 C21 30.6(3)
N2 C22 C21 C20 37.0(2)
N1 C8 C9 C10 -27.1(2)
N1 C7 B1 F3 -34.9(12)
N1 C7 B1 F2 91.1(14)
N1 C7 B1 F1 -148.6(9)
N1 C7 B1 F2A 73.3(6)
N1 C7 B1 F3A -45.7(8)
N1 C7 B1 F1A -169.2(10)
N1 C11 C10 C9 -37.7(3)
C5 C4 C3 C2 -2.9(3)
C5 C4 C7 N1 63.7(3)
C5 C4 C7 B1 -116.6(3)
C5 C6 C1 Br1 179.25(16)
C5 C6 C1 C2 -0.9(3)
C18 N2 C19 C20 179.1(2)
C18 N2 C22 C21 154.9(2)
C18 C15 C14 C13 174.0(2)
C18 C15 C16 C17 -171.7(2)
C15 C18 B2 F6 -129.5(2)
C15 C18 B2 F4 -9.9(3)
C15 C18 B2 F5 110.3(2)
C4 C5 C6 C1 1.1(3)
C4 C3 C2 C1 3.0(3)
C4 C7 B1 F3 145.3(12)
C4 C7 B1 F2 -88.7(14)
C4 C7 B1 F1 31.6(10)
C4 C7 B1 F2A -106.5(6)
C4 C7 B1 F3A 134.5(8)
C4 C7 B1 F1A 11.1(10)
C13 C12 C17 C16 -1.0(3)
C8 N1 C7 C4 0.8(3)
C8 N1 C7 B1 -178.9(2)
C8 N1 C11 C10 21.3(3)
C8 C9 C10 C11 40.5(3)
C6 C5 C4 C3 0.8(3)
C6 C5 C4 C7 177.5(2)
C12 C13 C14 C15 -2.2(3)
C12 C17 C16 C15 -1.6(3)
C19 N2 C18 C15 -2.1(3)
C19 N2 C18 B2 176.2(2)
C19 N2 C22 C21 -18.3(3)
C19 C20 C21 C22 -41.9(3)
C14 C15 C16 C17 2.3(3)
C14 C13 C12 Br2 -176.77(17)
C14 C13 C12 C17 3.0(3)
C3 C4 C7 N1 -119.5(2)
C3 C4 C7 B1 60.2(3)
C3 C2 C1 Br1 178.70(16)
C3 C2 C1 C6 -1.1(3)
C22 N2 C18 C15 -174.1(2)
C22 N2 C18 B2 4.2(3)
C22 N2 C19 C20 -7.9(3)
C7 N1 C8 C9 178.9(2)
C7 N1 C11 C10 -154.3(2)
C7 C4 C3 C2 -179.8(2)
C16 C15 C14 C13 -0.4(3)
C11 N1 C8 C9 3.4(2)
C11 N1 C7 C4 175.7(2)
C11 N1 C7 B1 -4.1(4)
B2 C18 C15 C14 -62.7(3)
B2 C18 C15 C16 111.4(2)