#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:00:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269695 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243327.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_7243327
loop_
_publ_author_name
'Peloquin, Andrew J.'
'McMillen, Colin D.'
'Pennington, William T.'
_publ_section_title
;
 One dimensional halogen bond design: Br⋯N versus I⋯N with
 fluoroarenes
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6098
_journal_page_last               6106
_journal_paper_doi               10.1039/D1CE00864A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '3(Br2 C12 F8), 1.5(C6 H12 N2)'
_chemical_formula_sum            'C45 H18 Br6 F24 N3'
_chemical_formula_weight         1536.047
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                91.873(11)
_cell_angle_beta                 94.086(13)
_cell_angle_gamma                105.304(11)
_cell_formula_units_Z            2
_cell_length_a                   7.938(3)
_cell_length_b                   10.577(4)
_cell_length_c                   29.826(11)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.725
_cell_measurement_theta_min      2.486
_cell_volume                     2405.8(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            69289
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.139
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8066.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1468.720
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.0381
_refine_diff_density_min         -1.0778
_refine_diff_density_rms         0.1278
_refine_ls_d_res_high            0.7697
_refine_ls_d_res_low             9.7984
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     739
_refine_ls_number_reflns         11063
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.0675
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0100P)²+3.7078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                9123
_reflns_number_total             11063
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce00864a2.cif
_cod_data_source_block           3Br2F8bph_2DABCO
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7243307--7243335.cif.
;
_cod_original_cell_volume        2405.8(15)
_cod_database_code               7243327
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
N4 \\sim C44 \\sim C46 \\sim C48: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.1 within 2A
N3 \\sim C43 \\sim C45 \\sim C47: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.1 within 2A
2. Others
 Fixed Sof: N3(0.5) N4(0.5) C43(0.5) H43a(0.5) H43b(0.5) C44(0.5) H44a(0.5)
 H44b(0.5) C45(0.5) H45a(0.5) H45b(0.5) C46(0.5) H46a(0.5) H46b(0.5) C47(0.5)
 H47a(0.5) H47b(0.5) C48(0.5) H48a(0.5) H48b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C37(H37a,H37b), C38(H38a,H38b), C39(H39a,H39b), C40(H40a,H40b), C41(H41a,
 H41b), C42(H42a,H42b), C43(H43a,H43b), C44(H44a,H44b), C45(H45a,H45b),
 C46(H46a,H46b), C47(H47a,H47b), C48(H48a,H48b)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Br1 Br 0.11023(3) -0.17132(3) 0.115360(9) 0.01836(6) Uani 1.000000 . . .
Br2 Br 1.33074(4) 0.20838(3) 0.325581(10) 0.02739(7) Uani 1.000000 . . .
F1 F 0.3729(2) 0.09921(15) 0.12026(5) 0.0219(3) Uani 1.000000 . . .
F2 F 0.6623(2) 0.19527(15) 0.17474(5) 0.0213(3) Uani 1.000000 . . .
F3 F 0.5798(2) -0.21483(15) 0.24114(5) 0.0209(3) Uani 1.000000 . . .
F4 F 0.2829(2) -0.30841(15) 0.18889(5) 0.0222(3) Uani 1.000000 . . .
F5 F 1.0116(2) 0.31663(16) 0.31741(6) 0.0259(4) Uani 1.000000 . . .
F6 F 0.7053(2) 0.22169(15) 0.26841(6) 0.0239(4) Uani 1.000000 . . .
F7 F 0.9108(2) -0.12605(15) 0.21025(5) 0.0232(4) Uani 1.000000 . . .
F8 F 1.2138(2) -0.03392(17) 0.26035(6) 0.0261(4) Uani 1.000000 . . .
C1 C 0.3191(3) -0.1075(3) 0.15295(9) 0.0163(5) Uani 1.000000 . . .
C2 C 0.4208(4) 0.0204(3) 0.15056(9) 0.0167(5) Uani 1.000000 . . .
C3 C 0.5711(4) 0.0699(2) 0.17854(9) 0.0162(5) Uani 1.000000 . . .
C4 C 0.6311(3) -0.0065(2) 0.20960(8) 0.0134(5) Uani 1.000000 . . .
C5 C 0.5295(4) -0.1355(3) 0.21152(9) 0.0170(5) Uani 1.000000 . . .
C6 C 0.3766(4) -0.1847(3) 0.18429(9) 0.0165(5) Uani 1.000000 . . .
C7 C 1.1178(4) 0.1422(3) 0.29063(9) 0.0180(5) Uani 1.000000 . . .
C8 C 0.9870(4) 0.2065(3) 0.29145(9) 0.0180(5) Uani 1.000000 . . .
C9 C 0.8304(4) 0.1579(3) 0.26585(9) 0.0172(5) Uani 1.000000 . . .
C10 C 0.7984(3) 0.0443(2) 0.23806(8) 0.0150(5) Uani 1.000000 . . .
C11 C 0.9313(4) -0.0176(3) 0.23745(9) 0.0165(5) Uani 1.000000 . . .
C12 C 1.0886(4) 0.0295(3) 0.26314(9) 0.0178(5) Uani 1.000000 . . .
Br3 Br 0.76232(4) 0.23755(3) 0.052908(9) 0.01930(6) Uani 1.000000 . . .
Br6 Br 1.96387(4) 0.59853(3) 0.272201(10) 0.02702(7) Uani 1.000000 . . .
F9 F 0.9102(2) 0.10606(15) 0.13240(6) 0.0224(3) Uani 1.000000 . . .
F10 F 1.2002(2) 0.19837(15) 0.18713(5) 0.0204(3) Uani 1.000000 . . .
F11 F 1.3505(2) 0.57910(14) 0.10426(5) 0.0208(3) Uani 1.000000 . . .
F12 F 1.0553(2) 0.49215(15) 0.05088(5) 0.0225(4) Uani 1.000000 . . .
F13 F 1.5837(2) 0.52705(17) 0.29597(5) 0.0267(4) Uani 1.000000 . . .
F14 F 1.2891(2) 0.43882(16) 0.24207(5) 0.0225(3) Uani 1.000000 . . .
F15 F 1.6220(2) 0.44496(16) 0.11689(5) 0.0235(4) Uani 1.000000 . . .
F16 F 1.9178(2) 0.53228(17) 0.17054(6) 0.0285(4) Uani 1.000000 . . .
C13 C 0.9725(3) 0.2972(3) 0.09026(9) 0.0165(5) Uani 1.000000 . . .
C14 C 1.0152(4) 0.2250(2) 0.12552(9) 0.0171(5) Uani 1.000000 . . .
C15 C 1.1655(4) 0.2726(3) 0.15358(9) 0.0163(5) Uani 1.000000 . . .
C16 C 1.2841(3) 0.3918(3) 0.14768(9) 0.0154(5) Uani 1.000000 . . .
C17 C 1.2411(3) 0.4624(2) 0.11210(9) 0.0161(5) Uani 1.000000 . . .
C18 C 1.0896(4) 0.4177(3) 0.08421(9) 0.0174(5) Uani 1.000000 . . .
C19 C 1.7581(4) 0.5333(3) 0.23454(9) 0.0181(5) Uani 1.000000 . . .
C20 C 1.5959(4) 0.5065(3) 0.25181(9) 0.0173(5) Uani 1.000000 . . .
C21 C 1.4440(4) 0.4608(3) 0.22403(9) 0.0161(5) Uani 1.000000 . . .
C22 C 1.4476(3) 0.4407(2) 0.17777(9) 0.0145(5) Uani 1.000000 . . .
C23 C 1.6109(4) 0.4673(3) 0.16109(9) 0.0173(5) Uani 1.000000 . . .
C24 C 1.7642(4) 0.5121(3) 0.18851(10) 0.0191(6) Uani 1.000000 . . .
Br4 Br 0.46531(5) 0.90085(4) 0.338101(12) 0.03643(9) Uani 1.000000 . . .
Br5 Br 1.20601(4) 0.23379(3) 0.463784(10) 0.02516(7) Uani 1.000000 . . .
F17 F 0.3317(2) 0.63872(18) 0.38157(6) 0.0324(4) Uani 1.000000 . . .
F18 F 0.5122(2) 0.47871(16) 0.41575(6) 0.0261(4) Uani 1.000000 . . .
F19 F 1.0361(2) 0.76207(16) 0.37290(5) 0.0233(4) Uani 1.000000 . . .
F20 F 0.8578(2) 0.92609(17) 0.34168(6) 0.0299(4) Uani 1.000000 . . .
F21 F 1.2642(2) 0.52800(16) 0.48680(5) 0.0247(4) Uani 1.000000 . . .
F22 F 1.0782(2) 0.69040(15) 0.45872(5) 0.0219(3) Uani 1.000000 . . .
F23 F 0.6964(2) 0.34448(16) 0.36735(6) 0.0288(4) Uani 1.000000 . . .
F24 F 0.8752(3) 0.17978(16) 0.39769(6) 0.0340(4) Uani 1.000000 . . .
C25 C 0.5906(4) 0.7860(3) 0.36085(10) 0.0219(6) Uani 1.000000 . . .
C26 C 0.5059(4) 0.6708(3) 0.37963(9) 0.0212(6) Uani 1.000000 . . .
C27 C 0.6000(4) 0.5879(3) 0.39695(9) 0.0195(6) Uani 1.000000 . . .
C28 C 0.7803(4) 0.6151(3) 0.39541(9) 0.0174(5) Uani 1.000000 . . .
C29 C 0.8623(4) 0.7309(3) 0.37642(9) 0.0191(6) Uani 1.000000 . . .
C30 C 0.7701(4) 0.8155(3) 0.35959(9) 0.0210(6) Uani 1.000000 . . .
C31 C 1.0744(4) 0.3492(3) 0.44343(9) 0.0203(6) Uani 1.000000 . . .
C32 C 1.1226(4) 0.4800(3) 0.45760(9) 0.0192(6) Uani 1.000000 . . .
C33 C 1.0272(4) 0.5643(3) 0.44258(9) 0.0184(5) Uani 1.000000 . . .
C34 C 0.8799(4) 0.5231(3) 0.41213(9) 0.0169(5) Uani 1.000000 . . .
C35 C 0.8343(4) 0.3911(3) 0.39793(9) 0.0204(6) Uani 1.000000 . . .
C36 C 0.9277(4) 0.3066(3) 0.41326(10) 0.0232(6) Uani 1.000000 . . .
N1 N -0.1927(3) -0.2188(2) 0.05750(7) 0.0161(5) Uani 1.000000 . . .
N2 N -0.4475(3) -0.1947(2) 0.00274(7) 0.0164(5) Uani 1.000000 . . .
C37 C -0.1293(4) -0.1162(3) 0.02585(9) 0.0188(6) Uani 1.000000 . . .
H37a H -0.0847(4) -0.0301(3) 0.04264(9) 0.0226(7) Uiso 1.000000 R . .
H37b H -0.0315(4) -0.1352(3) 0.01049(9) 0.0226(7) Uiso 1.000000 R . .
C38 C -0.2794(4) -0.1102(3) -0.00968(9) 0.0190(6) Uani 1.000000 . . .
H38a H -0.2542(4) -0.1400(3) -0.03968(9) 0.0228(7) Uiso 1.000000 R . .
H38b H -0.2871(4) -0.0185(3) -0.01134(9) 0.0228(7) Uiso 1.000000 R . .
C39 C -0.2721(4) -0.3434(3) 0.03132(9) 0.0201(6) Uani 1.000000 . . .
H39a H -0.1856(4) -0.3643(3) 0.01204(9) 0.0241(7) Uiso 1.000000 R . .
H39b H -0.3070(4) -0.4153(3) 0.05201(9) 0.0241(7) Uiso 1.000000 R . .
C40 C -0.4359(4) -0.3318(3) 0.00144(10) 0.0204(6) Uani 1.000000 . . .
H40a H -0.5430(4) -0.3893(3) 0.01242(10) 0.0244(7) Uiso 1.000000 R . .
H40b H -0.4278(4) -0.3614(3) -0.02998(10) 0.0244(7) Uiso 1.000000 R . .
C41 C -0.3277(4) -0.1827(3) 0.08267(9) 0.0186(5) Uani 1.000000 . . .
H41a H -0.3796(4) -0.2545(3) 0.10211(9) 0.0223(7) Uiso 1.000000 R . .
H41b H -0.2738(4) -0.1027(3) 0.10221(9) 0.0223(7) Uiso 1.000000 R . .
C42 C -0.4736(4) -0.1573(3) 0.04930(9) 0.0188(6) Uani 1.000000 . . .
H42a H -0.4709(4) -0.0632(3) 0.05159(9) 0.0226(7) Uiso 1.000000 R . .
H42b H -0.5898(4) -0.2090(3) 0.05729(9) 0.0226(7) Uiso 1.000000 R . .
N3 N 1.416(2) 0.0836(15) 0.4881(6) 0.019(2) Uani 0.500000 . U -1
N4 N 1.612(2) -0.0670(15) 0.5086(6) 0.021(2) Uani 0.500000 . U -1
C43 C 1.5736(8) 0.1165(6) 0.4624(2) 0.0234(12) Uani 0.500000 . U -1
H43a H 1.5377(8) 0.1067(6) 0.4297(2) 0.0281(14) Uiso 0.500000 R . -1
H43b H 1.6407(8) 0.2089(6) 0.4698(2) 0.0281(14) Uiso 0.500000 R . -1
C44 C 1.6907(8) 0.0236(6) 0.4744(2) 0.0226(12) Uani 0.500000 . U -1
H44a H 1.8090(8) 0.0763(6) 0.4862(2) 0.0271(14) Uiso 0.500000 R . -1
H44b H 1.7029(8) -0.0274(6) 0.4470(2) 0.0271(14) Uiso 0.500000 R . -1
C45 C 1.4714(8) 0.0998(6) 0.5359(2) 0.0248(12) Uani 0.500000 . U -1
H45a H 1.5354(8) 0.1926(6) 0.5437(2) 0.0298(15) Uiso 0.500000 R . -1
H45b H 1.3671(8) 0.0777(6) 0.5534(2) 0.0298(15) Uiso 0.500000 R . -1
C46 C 1.5920(8) 0.0101(6) 0.54880(19) 0.0236(12) Uani 0.500000 . U -1
H46a H 1.5400(8) -0.0497(6) 0.57200(19) 0.0284(15) Uiso 0.500000 R . -1
H46b H 1.7082(8) 0.0645(6) 0.56145(19) 0.0284(15) Uiso 0.500000 R . -1
C47 C 1.3191(8) -0.0544(5) 0.4768(2) 0.0236(12) Uani 0.500000 . U -1
H47a H 1.2119(8) -0.0772(5) 0.4932(2) 0.0283(15) Uiso 0.500000 R . -1
H47b H 1.2834(8) -0.0667(5) 0.4441(2) 0.0283(15) Uiso 0.500000 R . -1
C48 C 1.4375(8) -0.1460(5) 0.4901(2) 0.0251(13) Uani 0.500000 . U -1
H48a H 1.4493(8) -0.1996(5) 0.4632(2) 0.0301(15) Uiso 0.500000 R . -1
H48b H 1.3825(8) -0.2063(5) 0.5128(2) 0.0301(15) Uiso 0.500000 R . -1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_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_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C2 C1 Br1 120.62(19) . . ?
C6 C1 Br1 122.0(2) . . ?
C6 C1 C2 117.3(2) . . ?
C1 C2 F1 119.9(2) . . ?
C3 C2 F1 118.6(2) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 F2 118.3(2) . . ?
C4 C3 F2 119.9(2) . . ?
C4 C3 C2 121.8(2) . . ?
C5 C4 C3 116.5(2) . . ?
C10 C4 C3 121.9(2) . . ?
C10 C4 C5 121.5(2) . . ?
C4 C5 F3 119.5(2) . . ?
C6 C5 F3 118.4(2) . . ?
C6 C5 C4 122.0(2) . . ?
C1 C6 F4 120.4(2) . . ?
C5 C6 F4 118.7(2) . . ?
C5 C6 C1 120.9(2) . . ?
C8 C7 Br2 120.5(2) . . ?
C12 C7 Br2 120.9(2) . . ?
C12 C7 C8 118.6(2) . . ?
C7 C8 F5 120.1(2) . . ?
C9 C8 F5 119.3(2) . . ?
C9 C8 C7 120.5(2) . . ?
C8 C9 F6 118.6(2) . . ?
C10 C9 F6 119.7(2) . . ?
C10 C9 C8 121.7(2) . . ?
C9 C10 C4 121.7(2) . . ?
C11 C10 C4 121.4(2) . . ?
C11 C10 C9 116.8(2) . . ?
C10 C11 F7 119.9(2) . . ?
C12 C11 F7 117.9(2) . . ?
C12 C11 C10 122.2(2) . . ?
C7 C12 F8 120.6(2) . . ?
C11 C12 F8 119.3(2) . . ?
C11 C12 C7 120.1(2) . . ?
C14 C13 Br3 121.9(2) . . ?
C18 C13 Br3 120.8(2) . . ?
C18 C13 C14 117.3(2) . . ?
C13 C14 F9 120.3(2) . . ?
C15 C14 F9 118.6(2) . . ?
C15 C14 C13 121.1(2) . . ?
C14 C15 F10 118.5(2) . . ?
C16 C15 F10 119.2(2) . . ?
C16 C15 C14 122.2(2) . . ?
C17 C16 C15 116.2(2) . . ?
C22 C16 C15 121.6(2) . . ?
C22 C16 C17 122.2(2) . . ?
C16 C17 F11 119.5(2) . . ?
C18 C17 F11 118.1(2) . . ?
C18 C17 C16 122.5(2) . . ?
C13 C18 F12 120.0(2) . . ?
C17 C18 F12 119.2(2) . . ?
C17 C18 C13 120.8(2) . . ?
C20 C19 Br6 120.7(2) . . ?
C24 C19 Br6 120.9(2) . . ?
C24 C19 C20 118.4(2) . . ?
C19 C20 F13 120.4(2) . . ?
C21 C20 F13 118.7(2) . . ?
C21 C20 C19 120.8(2) . . ?
C20 C21 F14 118.9(2) . . ?
C22 C21 F14 119.6(2) . . ?
C22 C21 C20 121.6(2) . . ?
C21 C22 C16 121.7(2) . . ?
C23 C22 C16 121.4(2) . . ?
C23 C22 C21 116.9(2) . . ?
C22 C23 F15 119.3(2) . . ?
C24 C23 F15 118.4(2) . . ?
C24 C23 C22 122.3(2) . . ?
C19 C24 F16 120.5(2) . . ?
C23 C24 F16 119.4(2) . . ?
C23 C24 C19 120.1(3) . . ?
C26 C25 Br4 121.0(2) . . ?
C30 C25 Br4 120.5(2) . . ?
C30 C25 C26 118.5(2) . . ?
C25 C26 F17 120.4(2) . . ?
C27 C26 F17 119.1(3) . . ?
C27 C26 C25 120.5(3) . . ?
C26 C27 F18 118.2(2) . . ?
C28 C27 F18 120.0(2) . . ?
C28 C27 C26 121.8(3) . . ?
C29 C28 C27 116.7(2) . . ?
C34 C28 C27 121.7(2) . . ?
C34 C28 C29 121.6(2) . . ?
C28 C29 F19 119.9(2) . . ?
C30 C29 F19 118.0(2) . . ?
C30 C29 C28 122.0(3) . . ?
C25 C30 F20 120.6(2) . . ?
C29 C30 F20 119.0(3) . . ?
C29 C30 C25 120.5(3) . . ?
C32 C31 Br5 121.2(2) . . ?
C36 C31 Br5 121.6(2) . . ?
C36 C31 C32 117.2(2) . . ?
C31 C32 F21 120.3(2) . . ?
C33 C32 F21 118.6(2) . . ?
C33 C32 C31 121.2(3) . . ?
C32 C33 F22 118.3(2) . . ?
C34 C33 F22 119.3(2) . . ?
C34 C33 C32 122.3(2) . . ?
C33 C34 C28 122.0(2) . . ?
C35 C34 C28 122.4(2) . . ?
C35 C34 C33 115.6(2) . . ?
C34 C35 F23 119.2(2) . . ?
C36 C35 F23 118.6(2) . . ?
C36 C35 C34 122.2(3) . . ?
C31 C36 F24 120.0(2) . . ?
C35 C36 F24 118.5(3) . . ?
C35 C36 C31 121.5(3) . . ?
C39 N1 C37 108.3(2) . . ?
C41 N1 C37 108.6(2) . . ?
C41 N1 C39 109.0(2) . . ?
C40 N2 C38 108.2(2) . . ?
C42 N2 C38 108.8(2) . . ?
C42 N2 C40 108.2(2) . . ?
H37a C37 N1 109.55(14) . . ?
H37b C37 N1 109.55(14) . . ?
H37b C37 H37a 108.1 . . ?
C38 C37 N1 110.5(2) . . ?
C38 C37 H37a 109.55(15) . . ?
C38 C37 H37b 109.55(15) . . ?
C37 C38 N2 109.9(2) . . ?
H38a C38 N2 109.68(14) . . ?
H38a C38 C37 109.68(15) . . ?
H38b C38 N2 109.68(14) . . ?
H38b C38 C37 109.68(15) . . ?
H38b C38 H38a 108.2 . . ?
H39a C39 N1 109.71(15) . . ?
H39b C39 N1 109.71(14) . . ?
H39b C39 H39a 108.2 . . ?
C40 C39 N1 109.8(2) . . ?
C40 C39 H39a 109.71(15) . . ?
C40 C39 H39b 109.71(15) . . ?
C39 C40 N2 110.4(2) . . ?
H40a C40 N2 109.57(14) . . ?
H40a C40 C39 109.57(15) . . ?
H40b C40 N2 109.57(14) . . ?
H40b C40 C39 109.57(15) . . ?
H40b C40 H40a 108.1 . . ?
H41a C41 N1 109.68(14) . . ?
H41b C41 N1 109.68(13) . . ?
H41b C41 H41a 108.2 . . ?
C42 C41 N1 109.9(2) . . ?
C42 C41 H41a 109.68(14) . . ?
C42 C41 H41b 109.68(14) . . ?
C41 C42 N2 110.4(2) . . ?
H42a C42 N2 109.58(14) . . ?
H42a C42 C41 109.58(14) . . ?
H42b C42 N2 109.58(14) . . ?
H42b C42 C41 109.58(14) . . ?
H42b C42 H42a 108.1 . . ?
C45 N3 C43 108.9(12) . . ?
C47 N3 C43 108.8(11) . . ?
C47 N3 C45 109.2(10) . . ?
C46 N4 C44 109.0(10) . . ?
C48 N4 C44 108.8(12) . . ?
C48 N4 C46 108.8(11) . . ?
H43a C43 N3 109.8(8) . . ?
H43b C43 N3 109.8(7) . . ?
H43b C43 H43a 108.2 . . ?
C44 C43 N3 109.6(8) . . ?
C44 C43 H43a 109.8(3) . . ?
C44 C43 H43b 109.8(3) . . ?
C43 C44 N4 110.3(9) . . ?
H44a C44 N4 109.6(8) . . ?
H44a C44 C43 109.6(3) . . ?
H44b C44 N4 109.6(7) . . ?
H44b C44 C43 109.6(3) . . ?
H44b C44 H44a 108.1 . . ?
H45a C45 N3 109.5(6) . . ?
H45b C45 N3 109.5(6) . . ?
H45b C45 H45a 108.0 . . ?
C46 C45 N3 110.9(8) . . ?
C46 C45 H45a 109.5(3) . . ?
C46 C45 H45b 109.5(3) . . ?
C45 C46 N4 109.5(9) . . ?
H46a C46 N4 109.8(6) . . ?
H46a C46 C45 109.8(3) . . ?
H46b C46 N4 109.8(7) . . ?
H46b C46 C45 109.8(3) . . ?
H46b C46 H46a 108.2 . . ?
H47a C47 N3 109.7(6) . . ?
H47b C47 N3 109.7(7) . . ?
H47b C47 H47a 108.2 . . ?
C48 C47 N3 109.7(9) . . ?
C48 C47 H47a 109.7(3) . . ?
C48 C47 H47b 109.7(3) . . ?
C47 C48 N4 110.1(8) . . ?
H48a C48 N4 109.6(7) . . ?
H48a C48 C47 109.6(3) . . ?
H48b C48 N4 109.6(7) . . ?
H48b C48 C47 109.6(3) . . ?
H48b C48 H48a 108.2 . . ?
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
Br1 C1 1.886(3) . ?
Br2 C7 1.874(3) . ?
F1 C2 1.350(3) . ?
F2 C3 1.345(3) . ?
F3 C5 1.349(3) . ?
F4 C6 1.340(3) . ?
F5 C8 1.340(3) . ?
F6 C9 1.345(3) . ?
F7 C11 1.350(3) . ?
F8 C12 1.343(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.389(3) . ?
C4 C5 1.395(4) . ?
C4 C10 1.485(3) . ?
C5 C6 1.379(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.382(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.380(4) . ?
C11 C12 1.381(4) . ?
Br3 C13 1.886(3) . ?
Br6 C19 1.870(3) . ?
F9 C14 1.345(3) . ?
F10 C15 1.349(3) . ?
F11 C17 1.347(3) . ?
F12 C18 1.345(3) . ?
F13 C20 1.342(3) . ?
F14 C21 1.345(3) . ?
F15 C23 1.345(3) . ?
F16 C24 1.336(3) . ?
C13 C14 1.394(4) . ?
C13 C18 1.390(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.385(4) . ?
C16 C17 1.391(4) . ?
C16 C22 1.485(4) . ?
C17 C18 1.376(4) . ?
C19 C20 1.384(4) . ?
C19 C24 1.390(4) . ?
C20 C21 1.378(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.385(4) . ?
C23 C24 1.379(4) . ?
Br4 C25 1.876(3) . ?
Br5 C31 1.893(3) . ?
F17 C26 1.340(3) . ?
F18 C27 1.344(3) . ?
F19 C29 1.344(3) . ?
F20 C30 1.343(3) . ?
F21 C32 1.346(3) . ?
F22 C33 1.349(3) . ?
F23 C35 1.348(3) . ?
F24 C36 1.351(3) . ?
C25 C26 1.384(4) . ?
C25 C30 1.380(4) . ?
C26 C27 1.384(4) . ?
C27 C28 1.388(4) . ?
C28 C29 1.386(4) . ?
C28 C34 1.484(4) . ?
C29 C30 1.382(4) . ?
C31 C32 1.378(4) . ?
C31 C36 1.384(4) . ?
C32 C33 1.379(4) . ?
C33 C34 1.392(4) . ?
C34 C35 1.391(4) . ?
C35 C36 1.373(4) . ?
N1 C37 1.473(3) . ?
N1 C39 1.472(3) . ?
N1 C41 1.473(3) . ?
N2 C38 1.476(3) . ?
N2 C40 1.477(3) . ?
N2 C42 1.475(3) . ?
C37 H37a 0.9900 . ?
C37 H37b 0.9900 . ?
C37 C38 1.553(4) . ?
C38 H38a 0.9900 . ?
C38 H38b 0.9900 . ?
C39 H39a 0.9900 . ?
C39 H39b 0.9900 . ?
C39 C40 1.557(4) . ?
C40 H40a 0.9900 . ?
C40 H40b 0.9900 . ?
C41 H41a 0.9900 . ?
C41 H41b 0.9900 . ?
C41 C42 1.556(4) . ?
C42 H42a 0.9900 . ?
C42 H42b 0.9900 . ?
N3 C43 1.483(15) . ?
N3 C45 1.452(19) . ?
N3 C47 1.475(15) . ?
N4 C44 1.478(14) . ?
N4 C46 1.471(18) . ?
N4 C48 1.475(17) . ?
C43 H43a 0.9900 . ?
C43 H43b 0.9900 . ?
C43 C44 1.554(8) . ?
C44 H44a 0.9900 . ?
C44 H44b 0.9900 . ?
C45 H45a 0.9900 . ?
C45 H45b 0.9900 . ?
C45 C46 1.554(8) . ?
C46 H46a 0.9900 . ?
C46 H46b 0.9900 . ?
C47 H47a 0.9900 . ?
C47 H47b 0.9900 . ?
C47 C48 1.559(8) . ?
C48 H48a 0.9900 . ?
C48 H48b 0.9900 . ?
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
Br1 C1 C2 F1 -1.8(2) . . . . ?
Br1 C1 C2 C3 178.2(2) . . . . ?
Br1 C1 C6 F4 -0.5(2) . . . . ?
Br1 C1 C6 C5 -179.7(2) . . . . ?
Br2 C7 C8 F5 -0.2(2) . . . . ?
Br2 C7 C8 C9 -179.9(2) . . . . ?
Br2 C7 C12 F8 -1.1(2) . . . . ?
Br2 C7 C12 C11 -179.7(2) . . . . ?
F1 C2 C1 C6 178.9(2) . . . . ?
F1 C2 C3 F2 0.8(3) . . . . ?
F1 C2 C3 C4 -178.1(2) . . . . ?
F2 C3 C2 C1 -179.2(2) . . . . ?
F2 C3 C4 C5 -180.0(2) . . . . ?
F2 C3 C4 C10 -2.4(3) . . . . ?
F3 C5 C4 C3 -179.6(2) . . . . ?
F3 C5 C4 C10 2.7(3) . . . . ?
F3 C5 C6 F4 1.1(3) . . . . ?
F3 C5 C6 C1 -179.6(2) . . . . ?
F4 C6 C1 C2 178.8(2) . . . . ?
F4 C6 C5 C4 -178.1(2) . . . . ?
F5 C8 C7 C12 -179.4(2) . . . . ?
F5 C8 C9 F6 -1.2(3) . . . . ?
F5 C8 C9 C10 179.5(2) . . . . ?
F6 C9 C8 C7 178.5(2) . . . . ?
F6 C9 C10 C4 2.2(3) . . . . ?
F6 C9 C10 C11 -179.1(2) . . . . ?
F7 C11 C10 C4 0.5(3) . . . . ?
F7 C11 C10 C9 -178.1(2) . . . . ?
F7 C11 C12 F8 -0.3(3) . . . . ?
F7 C11 C12 C7 178.3(2) . . . . ?
F8 C12 C7 C8 178.1(2) . . . . ?
F8 C12 C11 C10 -178.7(2) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C1 C6 C5 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 C10 176.5(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C10 C9 56.2(3) . . . . ?
C3 C4 C10 C11 -122.3(3) . . . . ?
C4 C10 C9 C8 -178.5(3) . . . . ?
C4 C10 C11 C12 179.0(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C12 C11 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
Br3 C13 C14 F9 3.5(2) . . . . ?
Br3 C13 C14 C15 -177.2(2) . . . . ?
Br3 C13 C18 F12 -1.2(2) . . . . ?
Br3 C13 C18 C17 178.6(2) . . . . ?
Br6 C19 C20 F13 0.1(2) . . . . ?
Br6 C19 C20 C21 178.8(2) . . . . ?
Br6 C19 C24 F16 3.0(2) . . . . ?
Br6 C19 C24 C23 -178.2(2) . . . . ?
F9 C14 C13 C18 -178.0(2) . . . . ?
F9 C14 C15 F10 -0.7(3) . . . . ?
F9 C14 C15 C16 177.4(2) . . . . ?
F10 C15 C14 C13 -180.0(2) . . . . ?
F10 C15 C16 C17 179.2(2) . . . . ?
F10 C15 C16 C22 -0.8(3) . . . . ?
F11 C17 C16 C15 -179.8(2) . . . . ?
F11 C17 C16 C22 0.1(3) . . . . ?
F11 C17 C18 F12 -1.0(3) . . . . ?
F11 C17 C18 C13 179.2(2) . . . . ?
F12 C18 C13 C14 -179.7(2) . . . . ?
F12 C18 C17 C16 179.0(2) . . . . ?
F13 C20 C19 C24 -179.2(2) . . . . ?
F13 C20 C21 F14 0.2(3) . . . . ?
F13 C20 C21 C22 178.3(2) . . . . ?
F14 C21 C20 C19 -178.5(2) . . . . ?
F14 C21 C22 C16 -1.8(3) . . . . ?
F14 C21 C22 C23 178.9(2) . . . . ?
F15 C23 C22 C16 -1.8(3) . . . . ?
F15 C23 C22 C21 177.5(2) . . . . ?
F15 C23 C24 F16 0.3(3) . . . . ?
F15 C23 C24 C19 -178.5(2) . . . . ?
F16 C24 C19 C20 -177.7(2) . . . . ?
F16 C24 C23 C22 178.1(2) . . . . ?
C13 C14 C15 C16 -1.9(3) . . . . ?
C13 C18 C17 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C22 -178.8(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C16 C22 C21 -58.8(3) . . . . ?
C15 C16 C22 C23 120.6(3) . . . . ?
C16 C22 C21 C20 -179.8(2) . . . . ?
C16 C22 C23 C24 -179.6(2) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C19 C24 C23 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
Br4 C25 C26 F17 0.5(3) . . . . ?
Br4 C25 C26 C27 -179.0(2) . . . . ?
Br4 C25 C30 F20 -0.7(3) . . . . ?
Br4 C25 C30 C29 179.9(2) . . . . ?
Br5 C31 C32 F21 -0.7(3) . . . . ?
Br5 C31 C32 C33 179.7(2) . . . . ?
Br5 C31 C36 F24 0.1(3) . . . . ?
Br5 C31 C36 C35 -178.8(2) . . . . ?
F17 C26 C25 C30 179.9(3) . . . . ?
F17 C26 C27 F18 -1.0(3) . . . . ?
F17 C26 C27 C28 179.2(2) . . . . ?
F18 C27 C26 C25 178.5(2) . . . . ?
F18 C27 C28 C29 -178.6(2) . . . . ?
F18 C27 C28 C34 3.0(3) . . . . ?
F19 C29 C28 C27 -178.5(2) . . . . ?
F19 C29 C28 C34 -0.1(3) . . . . ?
F19 C29 C30 F20 -1.8(3) . . . . ?
F19 C29 C30 C25 177.7(2) . . . . ?
F20 C30 C25 C26 180.0(3) . . . . ?
F20 C30 C29 C28 179.9(2) . . . . ?
F21 C32 C31 C36 -179.8(3) . . . . ?
F21 C32 C33 F22 -1.5(3) . . . . ?
F21 C32 C33 C34 179.5(2) . . . . ?
F22 C33 C32 C31 178.1(2) . . . . ?
F22 C33 C34 C28 2.4(3) . . . . ?
F22 C33 C34 C35 -178.7(2) . . . . ?
F23 C35 C34 C28 1.0(3) . . . . ?
F23 C35 C34 C33 -177.9(3) . . . . ?
F23 C35 C36 F24 -1.3(3) . . . . ?
F23 C35 C36 C31 177.6(3) . . . . ?
F24 C36 C31 C32 179.2(3) . . . . ?
F24 C36 C35 C34 -179.8(3) . . . . ?
C25 C26 C27 C28 -1.3(3) . . . . ?
C25 C30 C29 C28 -0.6(3) . . . . ?
C26 C27 C28 C29 1.2(3) . . . . ?
C26 C27 C28 C34 -177.2(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C27 C28 C34 C33 -128.7(3) . . . . ?
C27 C28 C34 C35 52.5(3) . . . . ?
C28 C34 C33 C32 -178.7(3) . . . . ?
C28 C34 C35 C36 179.5(3) . . . . ?
C31 C32 C33 C34 -0.9(3) . . . . ?
C31 C36 C35 C34 -0.8(4) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
N1 C37 C38 N2 8.6(2) . . . . ?
N1 C39 C40 N2 8.7(2) . . . . ?
N1 C41 C42 N2 8.0(2) . . . . ?
N3 C43 C44 N4 -1.4(15) . . . . ?
N3 C45 C46 N4 -0.9(11) . . . . ?
N3 C47 C48 N4 -1.7(13) . . . . ?
loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
N3 C43 0.0100
N3 C45 0.0100
N3 C47 0.0100
N4 C44 0.0100
N4 C46 0.0100
N4 C48 0.0100
