#------------------------------------------------------------------------------
#$Date: 2024-08-14 04:52:55 +0300 (Wed, 14 Aug 2024) $
#$Revision: 294106 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312578.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312578
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
Role of secondary interactions in a series of 2:1 halogen-bonded
cocrystals formed between 4-(dimethylamino)pyridine and ditopic
halogen-bond donors.
;
_journal_coeditor_code VP3039
_journal_issue 9
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi 10.1107/S205322962400771X
_journal_volume 80
_journal_year 2024
_chemical_formula_iupac '2C7 H10 N2, C6 Br F4 I'
_chemical_formula_moiety '2(C7 H10 N2), C6 Br F4 I'
_chemical_formula_sum 'C20 H20 Br F4 I N4'
_chemical_formula_weight 599.210
_chemical_name_systematic
;
4-(Dimethylamino)pyridine--1-bromo-4-iodo-2,3,5,6-tetrafluorobenzene (2/1)
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2ybc'
_space_group_name_H-M_alt 'P 1 21/c 1'
_atom_sites_solution_primary dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha 90
_cell_angle_beta 106.304(2)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 7.38980(10)
_cell_length_b 16.2120(2)
_cell_length_c 9.42360(10)
_cell_measurement_reflns_used 6158
_cell_measurement_temperature 100.01(15)
_cell_measurement_theta_max 77.1460
_cell_measurement_theta_min 2.6950
_cell_volume 1083.58(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al., 2015)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015)
;
_diffrn_ambient_temperature 100.01(15)
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method '\w scans'
_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 0.0419
_diffrn_reflns_av_unetI/netI 0.0331
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 10454
_diffrn_reflns_theta_full 67.6840
_diffrn_reflns_theta_max 77.78
_diffrn_reflns_theta_min 5.46
_diffrn_source 'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu 14.213
_exptl_absorpt_correction_T_max 0.595
_exptl_absorpt_correction_T_min 0.357
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_density_diffrn 1.837
_exptl_crystal_description irregular
_exptl_crystal_F_000 584.861
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.7481
_refine_diff_density_min -0.5799
_refine_ls_extinction_coef 0.00052(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.9978
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_constraints 17
_refine_ls_number_parameters 142
_refine_ls_number_reflns 2300
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 0.9974
_refine_ls_R_factor_all 0.0348
_refine_ls_R_factor_gt 0.0341
_refine_ls_shift/su_max -0.0003
_refine_ls_shift/su_mean 0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+7.3962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0797
_refine_ls_wR_factor_ref 0.0800
_reflns_number_gt 2252
_reflns_number_total 2300
_reflns_threshold_expression I>=2u(I)
_iucr_refine_instructions_details
;
TITL eb_a_188_1_auto_a.res in P2(1)/c
CELL 1.54184 7.3898 16.212 9.4236 90 106.304 90
ZERR 2 0.0001 0.0002 0.0001 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br F I N
UNIT 40 40 2 8 2 8
DFIX 1.85 C8 Br1
DFIX 2.09 C8 I1
EADP Br1 I1
L.S. 10
PLAN 20 0 0
SIZE 0.05 0.08 0.12
TEMP -173
CONF
BOND
FMAP 2 1 53
LIST 4 1
MORE -1
BOND $H
ACTA
EXTI 0.000517
WGHT 0 7.396198
FVAR 0.352459
REM
REM
REM
PART 2
Br1 3 0.59714 0.19937 0.51922 10.50000 0.01840 0.00755 0.01871 =
-0.00060 0.00365 -0.00090
PART 0
F1 4 0.85158 0.05177 0.50859 11.00000 0.01428 0.02284 0.02576 =
-0.00076 0.00627 -0.00280
F2 4 0.77553 -0.10968 0.49315 11.00000 0.01772 0.01876 0.03138 =
-0.00144 0.00767 0.00417
N2 6 0.82910 0.61742 0.51795 11.00000 0.03051 0.01714 0.02023 =
-0.00002 0.00415 -0.00494
N1 6 0.68384 0.36793 0.53764 11.00000 0.01741 0.02319 0.02573 =
0.00116 0.00511 0.00080
C9 1 0.67587 0.02705 0.50396 11.00000 0.01522 0.01902 0.01398 =
0.00145 0.00147 -0.00407
C8 1 0.54000 0.08564 0.50673 11.00000 0.01754 0.01463 0.01698 =
-0.00032 0.00421 -0.00137
C3 1 0.78139 0.53697 0.52506 11.00000 0.01866 0.01876 0.01910 =
-0.00313 0.00858 -0.00017
C4 1 0.83295 0.49144 0.65847 11.00000 0.01999 0.01936 0.01968 =
-0.00103 0.00583 0.00027
AFIX 43
H4 2 0.90346 0.51675 0.74781 11.00000 -1.20000
AFIX 0
C10 1 0.63743 -0.05620 0.49656 11.00000 0.01771 0.01746 0.01671 =
0.00050 0.00570 0.00230
C1 1 0.63202 0.41224 0.41110 11.00000 0.02216 0.02569 0.01802 =
-0.00350 0.00545 0.00028
AFIX 43
H1 2 0.55832 0.38523 0.32469 11.00000 -1.20000
AFIX 0
C5 1 0.77957 0.40978 0.65724 11.00000 0.02330 0.02185 0.01939 =
0.00088 0.00618 0.00204
AFIX 43
H5 2 0.81366 0.38106 0.74880 11.00000 -1.20000
AFIX 0
C2 1 0.67808 0.49345 0.39831 11.00000 0.02390 0.01998 0.01538 =
0.00058 0.00408 -0.00028
AFIX 43
H2 2 0.64072 0.52015 0.30488 11.00000 -1.20000
AFIX 0
C6 1 0.77495 0.66159 0.37881 11.00000 0.03331 0.01940 0.02507 =
0.00212 0.01013 0.00005
AFIX 137
H6a 2 0.82614 0.63322 0.30671 11.00000 -1.50000
H6b 2 0.63714 0.66353 0.34182 11.00000 -1.50000
H6c 2 0.82495 0.71789 0.39374 11.00000 -1.50000
AFIX 0
C7 1 0.92792 0.66203 0.65210 11.00000 0.03644 0.02037 0.02692 =
-0.00469 0.00413 -0.00852
AFIX 137
H7a 2 0.85281 0.66034 0.72280 11.00000 -1.50000
H7b 2 1.05071 0.63616 0.69621 11.00000 -1.50000
H7c 2 0.94650 0.71952 0.62722 11.00000 -1.50000
AFIX 0
PART 2
I1 5 0.60492 0.21223 0.51970 10.50000 0.01840 0.00755 0.01871 =
-0.00060 0.00365 -0.00090
HKLF 4
END
Q1 1 0.6 0.05 0.53125 11 0.05 0.75
Q2 1 0.68 0.183333 0.46875 11 0.05 0.74
REM The information below was added by Olex2.
REM
REM R1 = 0.0341 for 2252 Fo > 4sig(Fo) and 0.0348 for all 2300 data
REM 142 parameters refined using 2 restraints
REM Highest difference peak 0.7481, deepest hole -0.5799
REM Mean Shift 0.0000, Max Shift -0.0003.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0348
REM R1_gt = 0.0341
REM wR_ref = 0.0800
REM GOOF = 0.9978
REM Shift_max = -0.0003
REM Shift_mean = 0.0000
REM Reflections_all = 2300
REM Reflections_gt = 2252
REM Parameters = 142
REM Hole = -0.5799
REM Peak = 0.7481
REM Flack = n/a
;
_cod_data_source_file vp3039sup1.cif
_cod_data_source_block 2DMAP.IBTFB
_cod_database_code 2312578
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
loop_
_atom_site_type_symbol
_atom_site_label
_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_disorder_group
Br Br1 0.5971(11) 0.1994(3) 0.5192(9) 0.0152(3) Uani 0.500000 2
F F1 0.8516(3) 0.05177(14) 0.5086(3) 0.0208(5) Uani 1.000000 .
F F2 0.7755(3) -0.10968(14) 0.4932(3) 0.0225(5) Uani 1.000000 .
N N2 0.8291(5) 0.6174(2) 0.5179(4) 0.0232(7) Uani 1.000000 .
N N1 0.6838(5) 0.3679(2) 0.5376(4) 0.0223(7) Uani 1.000000 .
C C9 0.6759(5) 0.0271(2) 0.5040(4) 0.0166(7) Uani 1.000000 .
C C8 0.5400(5) 0.0856(2) 0.5067(4) 0.0165(7) Uani 1.000000 .
C C3 0.7814(5) 0.5370(2) 0.5251(4) 0.0182(7) Uani 1.000000 .
C C4 0.8329(5) 0.4914(2) 0.6585(4) 0.0196(8) Uani 1.000000 .
H H4 0.9035(5) 0.5168(2) 0.7478(4) 0.0236(9) Uiso 1.000000 .
C C10 0.6374(5) -0.0562(2) 0.4966(4) 0.0171(7) Uani 1.000000 .
C C1 0.6320(6) 0.4122(3) 0.4111(4) 0.0220(8) Uani 1.000000 .
H H1 0.5583(6) 0.3852(3) 0.3247(4) 0.0264(10) Uiso 1.000000 .
C C5 0.7796(6) 0.4098(3) 0.6572(5) 0.0215(8) Uani 1.000000 .
H H5 0.8137(6) 0.3811(3) 0.7488(5) 0.0258(10) Uiso 1.000000 .
C C2 0.6781(6) 0.4934(2) 0.3983(4) 0.0200(8) Uani 1.000000 .
H H2 0.6407(6) 0.5202(2) 0.3049(4) 0.0241(9) Uiso 1.000000 .
C C6 0.7750(6) 0.6616(3) 0.3788(5) 0.0255(9) Uani 1.000000 .
H H6a 0.826(4) 0.6332(11) 0.3067(12) 0.0383(13) Uiso 1.000000 .
H H6b 0.6371(6) 0.6635(18) 0.3418(19) 0.0383(13) Uiso 1.000000 .
H H6c 0.825(4) 0.7179(7) 0.3937(9) 0.0383(13) Uiso 1.000000 .
C C7 0.9279(7) 0.6620(3) 0.6521(5) 0.0289(9) Uani 1.000000 .
H H7a 0.853(2) 0.6603(19) 0.7228(16) 0.0433(14) Uiso 1.000000 .
H H7b 1.051(2) 0.6362(13) 0.696(2) 0.0433(14) Uiso 1.000000 .
H H7c 0.946(4) 0.7195(6) 0.6272(8) 0.0433(14) Uiso 1.000000 .
I I1 0.6049(7) 0.21223(17) 0.5197(5) 0.0152(3) Uani 0.500000 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0184(4) 0.0075(9) 0.01871(18) -0.0009(7) 0.0037(2) -0.0006(7)
F1 0.0143(10) 0.0228(12) 0.0258(12) -0.0028(9) 0.0063(9) -0.0008(9)
F2 0.0177(11) 0.0188(11) 0.0314(13) 0.0042(9) 0.0077(9) -0.0014(9)
N2 0.0305(18) 0.0171(16) 0.0202(17) -0.0049(14) 0.0042(14) 0.0000(13)
N1 0.0174(15) 0.0232(18) 0.0257(18) 0.0008(13) 0.0051(13) 0.0012(14)
C9 0.0152(16) 0.0190(19) 0.0140(17) -0.0041(14) 0.0015(13) 0.0014(14)
C8 0.0175(17) 0.0146(17) 0.0170(18) -0.0014(14) 0.0042(14) -0.0003(14)
C3 0.0187(17) 0.0188(18) 0.0191(18) -0.0002(15) 0.0086(15) -0.0031(15)
C4 0.0200(18) 0.0194(19) 0.0197(19) 0.0003(15) 0.0058(15) -0.0010(15)
C10 0.0177(17) 0.0175(18) 0.0167(18) 0.0023(14) 0.0057(14) 0.0005(14)
C1 0.0222(19) 0.026(2) 0.0180(19) 0.0003(16) 0.0055(15) -0.0035(16)
C5 0.0233(19) 0.022(2) 0.0194(19) 0.0020(16) 0.0062(15) 0.0009(15)
C2 0.0239(19) 0.0200(19) 0.0154(18) -0.0003(15) 0.0041(15) 0.0006(15)
C6 0.033(2) 0.019(2) 0.025(2) 0.0001(17) 0.0101(18) 0.0021(16)
C7 0.036(2) 0.020(2) 0.027(2) -0.0085(18) 0.0041(19) -0.0047(17)
I1 0.0184(4) 0.0075(9) 0.01871(18) -0.0009(7) 0.0037(2) -0.0006(7)
loop_
_atom_type_symbol
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_dispersion_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090 41.43280 2.95570
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
-0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.21560
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
F 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150 26.14760 0.27760
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.07537 0.05506 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.00304
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
I 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600 66.87760 4.07120
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
-0.19206 6.94430 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260 -11.52900
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
loop_
_diffrn_refln_index_h
_diffrn_refln_index_k
_diffrn_refln_index_l
0 0 -1
0 0 -2
0 0 -3
0 0 4
0 0 -4
0 0 -5
0 0 5
0 0 6
0 0 6
0 0 6
0 0 6
0 0 7
0 0 7
0 0 7
0 0 8
0 0 8
0 0 9
0 0 10
0 0 10
0 0 11
0 1 0
0 -1 -1
0 1 -2
0 -1 -2
0 -1 3
0 1 -3
0 -1 -3
0 1 -4
0 -1 4
0 -1 -4
0 1 5
0 -1 5
0 -1 -5
0 -1 6
0 1 6
0 -1 6
0 -1 -6
0 -1 6
0 -1 6
0 1 6
0 -1 6
0 1 7
0 -1 7
0 -1 7
0 -1 7
0 1 7
0 -1 7
0 1 8
0 -1 8
0 1 8
0 -1 8
0 -1 8
0 -1 9
0 1 9
0 -1 9
0 1 10
0 -1 10
0 1 10
0 1 11
0 2 0
0 -2 -1
0 -2 -2
0 -2 -3
0 -2 3
0 -2 4
0 -2 -4
0 -2 5
0 -2 -5
0 -2 6
0 -2 -6
0 2 6
0 -2 6
0 -2 6
0 2 6
0 -2 6
0 -2 7
0 -2 7
0 -2 -7
0 2 7
0 -2 7
0 2 7
0 -2 7
0 -2 8
0 2 8
0 -2 8
0 2 8
0 -2 9
0 2 9
0 -2 9
0 -2 10
0 2 10
0 -2 10
0 -2 10
0 -2 11
0 2 11
0 3 0
0 -3 -1
0 -3 -2
0 -3 -3
0 -3 3
0 -3 -4
0 -3 4
0 -3 -4
0 -3 5
0 -3 -5
0 -3 6
0 -3 -6
0 3 6
0 -3 6
0 -3 6
0 -3 6
0 -3 6
0 -3 6
0 -3 7
0 -3 7
0 -3 -7
0 3 7
0 -3 7
0 3 7
0 -3 7
0 -3 7
0 -3 8
0 3 8
0 3 8
0 -3 8
0 -3 9
0 3 9
0 -3 10
0 -3 10
0 3 10
0 -3 11
0 3 11
0 3 11
0 4 0
0 -4 -1
0 4 -1
0 -4 -2
0 -4 -3
0 -4 3
0 -4 -4
0 -4 4
0 -4 5
0 -4 -5
0 -4 6
0 -4 6
0 -4 6
0 -4 6
0 4 6
0 -4 6
0 -4 -6
0 -4 7
0 -4 7
0 4 7
0 -4 -7
0 4 7
0 -4 7
0 -4 7
0 -4 7
0 -4 8
0 4 8
0 -4 8
0 -4 8
0 -4 8
0 4 8
0 -4 9
0 4 9
0 -4 10
0 4 10
0 -4 10
0 -4 10
0 4 10
0 4 11
0 -4 11
0 5 0
0 -5 -1
0 5 -1
0 -5 -2
0 -5 -3
0 -5 -4
0 -5 -5
0 -5 6
0 5 6
0 -5 6
0 -5 6
0 -5 6
0 -5 -6
0 -5 -7
0 5 7
0 -5 7
0 -5 7
0 -5 7
0 -5 7
0 5 7
0 -5 7
0 5 8
0 -5 8
0 5 8
0 -5 8
0 -5 8
0 5 8
0 -5 8
0 -5 8
0 -5 9
0 -5 9
0 5 9
0 -5 9
0 -5 10
0 5 10
0 -5 10
0 -5 10
0 5 10
0 5 11
0 6 0
0 6 -1
0 -6 -1
0 6 -2
0 -6 -2
0 -6 -3
0 -6 -4
0 -6 -5
0 -6 5
0 -6 -5
0 -6 -6
0 -6 6
0 -6 6
0 6 6
0 -6 6
0 -6 6
0 -6 -7
0 -6 7
0 -6 7
0 6 7
0 -6 7
0 -6 7
0 -6 7
0 6 8
0 -6 8
0 -6 8
0 -6 8
0 -6 8
0 6 8
0 -6 8
0 6 9
0 -6 9
0 -6 9
0 -6 9
0 -6 9
0 6 9
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-8 -1 5
-8 1 5
-8 1 5
-8 -1 5
-8 1 5
-8 -1 4
-8 -1 4
-8 -1 4
-8 1 4
-8 -1 3
-8 -1 3
-8 1 3
-8 -1 3
-8 1 3
-8 1 3
-8 -1 2
-8 -1 2
-8 1 2
-8 -1 2
-8 1 2
-8 1 2
-8 1 1
-8 1 1
-8 1 1
-8 -1 1
-8 1 1
-8 -1 1
-8 1 1
-8 1 0
-8 -1 0
-8 1 0
-8 -1 0
-8 1 -1
-8 -1 -1
-8 1 -1
-8 -1 -1
-8 -1 -1
-8 1 -1
-8 -1 -2
-8 -1 -2
-8 1 -2
-8 -1 -2
-8 1 -2
-8 2 8
-8 2 8
-8 2 8
-8 2 8
-8 -2 7
-8 2 7
-8 -2 7
-8 2 7
-8 2 7
-8 2 7
-8 -2 6
-8 -2 6
-8 2 6
-8 -2 6
-8 -2 5
-8 2 5
-8 -2 5
-8 2 5
-8 2 5
-8 -2 4
-8 -2 4
-8 -2 4
-8 2 4
-8 -2 3
-8 -2 3
-8 2 3
-8 -2 3
-8 2 3
-8 2 3
-8 -2 3
-8 -2 2
-8 2 2
-8 -2 2
-8 2 2
-8 -2 2
-8 -2 2
-8 -2 2
-8 2 2
-8 2 1
-8 2 1
-8 -2 1
-8 -2 1
-8 -2 1
-8 -2 1
-8 2 1
-8 2 0
-8 -2 0
-8 -2 0
-8 2 0
-8 -2 0
-8 -2 -1
-8 2 -1
-8 -2 -1
-8 -2 -1
-8 -2 -1
-8 2 -1
-8 -2 -1
-8 -2 -2
-8 2 -2
-8 -2 -2
-8 2 -2
-8 -2 -2
-8 3 8
-8 3 8
-8 3 7
-8 3 7
-8 3 7
-8 3 7
-8 -3 7
-8 -3 6
-8 3 6
-8 3 6
-8 -3 6
-8 -3 6
-8 3 6
-8 3 6
-8 -3 5
-8 3 5
-8 3 5
-8 -3 5
-8 3 5
-8 3 5
-8 3 5
-8 3 4
-8 -3 4
-8 -3 4
-8 -3 4
-8 3 4
-8 3 4
-8 -3 3
-8 -3 3
-8 3 3
-8 -3 3
-8 3 3
-8 3 3
-8 -3 3
-8 -3 2
-8 -3 2
-8 3 2
-8 3 2
-8 -3 2
-8 -3 2
-8 -3 2
-8 3 2
-8 -3 1
-8 3 1
-8 -3 1
-8 -3 1
-8 -3 1
-8 -3 1
-8 3 1
-8 -3 0
-8 3 0
-8 -3 0
-8 -3 0
-8 -3 0
-8 -3 -1
-8 3 -1
-8 -3 -1
-8 -3 -1
-8 -3 -1
-8 3 -1
-8 -3 -1
-8 -3 -2
-8 3 -2
-8 -3 -2
-8 3 -2
-8 -3 -2
-8 4 8
-8 4 8
-8 4 7
-8 4 7
-8 4 6
-8 -4 6
-8 4 6
-8 4 6
-8 4 6
-8 -4 6
-8 4 6
-8 -4 5
-8 4 5
-8 -4 5
-8 -4 5
-8 4 5
-8 4 5
-8 4 5
-8 -4 4
-8 4 4
-8 -4 4
-8 4 4
-8 -4 4
-8 4 4
-8 4 3
-8 -4 3
-8 -4 3
-8 4 3
-8 -4 3
-8 4 3
-8 4 3
-8 4 2
-8 -4 2
-8 -4 2
-8 -4 2
-8 4 2
-8 4 2
-8 -4 2
-8 -4 2
-8 -4 2
-8 -4 1
-8 -4 1
-8 -4 1
-8 4 1
-8 4 1
-8 -4 1
-8 -4 1
8 -4 0
-8 -4 0
-8 4 0
-8 -4 0
-8 -4 0
-8 -4 0
-8 4 0
-8 -4 -1
-8 -4 -1
-8 4 -1
-8 -4 -1
-8 -4 -1
-8 -4 -2
-8 4 -2
-8 4 -2
-8 -4 -2
-8 5 8
-8 5 7
-8 5 7
-8 5 6
-8 5 6
-8 5 6
-8 5 6
-8 5 6
-8 -5 5
-8 5 5
-8 5 5
-8 5 5
-8 -5 4
-8 -5 4
-8 5 4
-8 5 4
-8 -5 3
-8 5 3
-8 5 3
-8 5 3
-8 5 3
-8 5 3
-8 5 2
-8 5 2
-8 -5 2
-8 -5 2
-8 -5 2
-8 5 2
-8 5 2
-8 -5 2
-8 -5 2
-8 -5 1
-8 -5 1
-8 -5 1
-8 5 1
-8 5 1
-8 -5 1
-8 -5 1
8 -5 0
-8 -5 0
-8 -5 0
-8 5 0
-8 5 0
-8 -5 0
-8 -5 -1
-8 -5 -1
-8 5 -1
8 -5 1
-8 -5 -2
-8 -5 -2
-8 5 -2
-8 6 7
-8 6 7
-8 6 6
-8 6 6
-8 6 6
-8 6 6
-8 6 5
-8 6 5
-8 6 5
-8 -6 5
-8 6 4
-8 6 4
-8 6 4
-8 6 3
-8 6 3
-8 6 3
-8 6 3
-8 6 3
-8 -6 3
-8 -6 2
-8 6 2
-8 -6 2
-8 6 2
-8 -6 2
-8 -6 1
-8 -6 1
-8 -6 1
-8 6 1
-8 6 1
-8 -6 0
8 -6 0
-8 -6 0
-8 -6 0
-8 6 0
8 -6 1
-8 -6 -1
-8 -6 -1
-8 6 -1
-8 7 7
-8 7 6
-8 7 6
-8 7 6
-8 7 5
-8 7 5
-8 7 5
-8 7 4
-8 7 4
-8 7 4
-8 7 4
-8 7 3
-8 7 3
-8 -7 3
-8 7 3
-8 7 3
-8 -7 2
-8 7 2
-8 -7 2
-8 7 2
-8 -7 1
-8 -7 1
-8 -7 1
-8 7 1
-8 7 1
-8 -7 0
-8 -7 0
-8 -7 0
-8 7 0
8 -7 0
-8 -7 -1
-8 -7 -1
-8 7 -1
-8 8 6
-8 8 6
-8 8 6
-8 8 6
-8 8 5
-8 8 5
-8 8 4
-8 8 4
-8 8 4
-8 8 4
-8 8 3
-8 8 3
-8 8 3
-8 -8 2
-8 -8 2
-8 8 2
-8 8 2
-8 -8 1
-8 8 1
-8 8 1
-8 -8 0
-8 8 0
8 -8 0
-8 8 -1
-8 9 6
-8 9 5
-8 9 5
-8 9 4
-8 9 4
-8 9 3
-8 9 3
-8 9 2
-8 9 2
-8 -9 1
-8 9 1
8 -9 0
-8 -9 0
-8 9 0
-8 10 4
-8 10 3
-8 10 2
8 -10 -1
-9 0 6
-9 0 5
-9 0 5
-9 0 4
-9 0 4
-9 0 3
-9 0 3
-9 0 2
-9 0 1
-9 0 1
-9 1 6
-9 1 6
-9 1 5
-9 -1 5
-9 1 5
-9 1 4
-9 -1 4
-9 1 4
-9 -1 4
-9 1 4
-9 -1 3
-9 1 3
-9 -1 3
-9 1 3
-9 -1 2
-9 1 2
-9 -1 1
-9 1 1
-9 -1 1
-9 1 1
-9 2 6
-9 2 5
-9 2 5
-9 2 4
-9 -2 4
-9 2 4
-9 2 4
-9 2 3
-9 2 3
-9 -2 2
-9 2 2
-9 -2 1
-9 2 1
-9 2 1
-9 3 5
-9 3 5
-9 -3 4
-9 3 4
-9 3 4
-9 3 3
-9 3 3
-9 -3 2
-9 -3 1
-9 4 5
-9 4 4
-9 -4 4
-9 4 3
-9 4 3
-9 -4 2
-9 5 4
-9 -5 3
-9 -5 2
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 -1 0.0415
-1 0 2 0.0459
-1 1 2 0.0529
0 2 1 0.0468
1 -1 -2 0.0469
-1 2 1 0.0621
1 2 -1 0.0414
0 -2 1 0.0433
0 2 -1 0.0441
2 0 -1 0.0372
-2 0 1 0.0519
-2 1 0 0.0447
2 -1 0 0.0267
-2 2 -1 0.0411
-2 0 -1 0.0322
1 1 -2 0.0381
-2 -1 -1 0.0310
2 1 1 0.0213
0 0 -1 0.0343
-1 -2 0 0.0423
1 -1 -1 0.0457
0 -4 1 0.0502
2 5 -3 0.0419
-1 -5 2 0.0472
-3 5 -1 0.0433
3 -4 2 0.0277
0 -3 -4 0.0388
0 2 3 0.0420
-1 -5 0 0.0490
1 5 0 0.0350
0 5 1 0.0464
4 -1 3 0.0177
0 0 1 0.0339
-3 -3 5 0.0417
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N2 C3 . . 120.7(3) ?
C7 N2 C3 . . 120.4(3) ?
C7 N2 C6 . . 118.8(3) ?
C5 N1 C1 . . 115.2(4) ?
C8 C9 F1 . . 119.4(3) ?
C10 C9 F1 . . 118.4(3) ?
C10 C9 C8 . . 122.1(3) ?
C9 C8 Br1 . . 121.3(4) ?
C10 C8 Br1 3_656 . 122.1(4) ?
C10 C8 C9 3_656 . 116.6(3) ?
I1 C8 C9 . . 121.0(3) ?
I1 C8 C10 . 3_656 122.4(3) ?
C4 C3 N2 . . 122.4(4) ?
C2 C3 N2 . . 121.6(4) ?
C2 C3 C4 . . 115.9(4) ?
H4 C4 C3 . . 120.4(2) ?
C5 C4 C3 . . 119.2(4) ?
C5 C4 H4 . . 120.4(2) ?
C9 C10 F2 . . 119.0(3) ?
C8 C10 F2 3_656 . 119.7(3) ?
C8 C10 C9 3_656 . 121.2(4) ?
H1 C1 N1 . . 117.6(2) ?
C2 C1 N1 . . 124.8(4) ?
C2 C1 H1 . . 117.6(2) ?
C4 C5 N1 . . 125.2(4) ?
H5 C5 N1 . . 117.4(2) ?
H5 C5 C4 . . 117.4(2) ?
C1 C2 C3 . . 119.5(4) ?
H2 C2 C3 . . 120.2(2) ?
H2 C2 C1 . . 120.2(2) ?
H6a C6 N2 . . 109.5 ?
H6b C6 N2 . . 109.5 ?
H6b C6 H6a . . 109.5 ?
H6c C6 N2 . . 109.5 ?
H6c C6 H6a . . 109.5 ?
H6c C6 H6b . . 109.5 ?
H7a C7 N2 . . 109.5 ?
H7b C7 N2 . . 109.5 ?
H7b C7 H7a . . 109.5 ?
H7c C7 N2 . . 109.5 ?
H7c C7 H7a . . 109.5 ?
H7c C7 H7b . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C8 . 1.888(6) ?
Br1 I1 . 0.216(8) ?
F1 C9 . 1.348(4) ?
F2 C10 . 1.346(4) ?
N2 C3 . 1.358(5) ?
N2 C6 . 1.448(5) ?
N2 C7 . 1.462(5) ?
N1 C1 . 1.352(5) ?
N1 C5 . 1.336(5) ?
C9 C8 . 1.388(5) ?
C9 C10 . 1.377(5) ?
C8 C10 3_656 1.387(5) ?
C8 I1 . 2.103(5) ?
C3 C4 . 1.415(6) ?
C3 C2 . 1.413(5) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.380(6) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.373(6) ?
C5 H5 . 0.9500 ?
C2 H2 . 0.9500 ?
C6 H6a . 0.9800 ?
C6 H6b . 0.9800 ?
C6 H6c . 0.9800 ?
C7 H7a . 0.9800 ?
C7 H7b . 0.9800 ?
C7 H7c . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C8 C9 F1 . . . . -0.8(4) ?
Br1 C8 C9 C10 . . . . 179.3(4) ?
Br1 C8 C10 F2 . . 3_656 3_656 1.1(5) ?
Br1 C8 C10 C9 . . 3_656 3_656 -179.2(4) ?
F1 C9 C8 C10 . . . 3_656 -179.3(3) ?
F1 C9 C8 I1 . . . . -0.5(4) ?
F1 C9 C10 F2 . . . . -0.5(4) ?
F1 C9 C10 C8 . . . 3_656 179.2(3) ?
F2 C10 C9 C8 . . . . 179.5(3) ?
F2 C10 C8 C9 . . 3_656 3_656 -179.6(3) ?
F2 C10 C8 I1 . . 3_656 3_656 -0.8(4) ?
N2 C3 C4 C5 . . . . -179.9(4) ?
N2 C3 C2 C1 . . . . -179.6(4) ?
N1 C1 C2 C3 . . . . -2.4(5) ?
N1 C5 C4 C3 . . . . 1.4(5) ?
C9 C8 C10 C9 . . 3_656 3_656 -0.7(3) ?
C9 C10 C8 C9 . . 3_656 3_656 0.7(4) ?
C9 C10 C8 I1 . . 3_656 3_656 179.5(3) ?
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
C8 Br1 1 1.8500 0.0200
C8 I1 1 2.0900 0.0200
_cod_database_fobs_code 2312578