#------------------------------------------------------------------------------
#$Date: 2020-12-30 02:46:27 +0200 (Wed, 30 Dec 2020) $
#$Revision: 260216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559883.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_1559883
loop_
_publ_author_name
'Zatsikha, Yuriy V.'
'Blesener, Tanner S.'
'King, Alex J.'
'Healy, Andrew T.'
'Goff, Philip C.'
'Didukh, Natalia O.'
'Blank, David A.'
'Kovtun, Yuriy P.'
'Nemykin, Victor N.'
_publ_section_related_literature
; 
? 
;
_publ_section_title
;
 Fully Conjugated Pyrene-BODIPY and Pyrene-BODIPY-Ferrocene Dyads and
 Triads: Synthesis, Characterization, and Selective Noncovalent
 Interactions with Nanocarbon Materials.
;
_journal_name_full               'The journal of physical chemistry. B'
_journal_paper_doi               10.1021/acs.jpcb.0c10074
_journal_year                    2020
_chemical_formula_moiety         'C47 H36 B1 Cl3 F2 N2 O4'
_chemical_formula_sum            'C47 H36 B Cl3 F2 N2 O4'
_chemical_formula_weight         847.98
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-18
_audit_creation_method           CRYSTALS_ver_14.61
_cell_angle_alpha                90
_cell_angle_beta                 110.060(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8942(2)
_cell_length_b                   24.6471(4)
_cell_length_c                   14.7953(10)
_cell_measurement_reflns_used    22435
_cell_measurement_temperature    123
_cell_measurement_theta_max      65
_cell_measurement_theta_min      2
_cell_volume                     4074.2(4)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22435
_diffrn_reflns_theta_full        25.376
_diffrn_reflns_theta_max         65.066
_diffrn_reflns_theta_min         3.587
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  2
_diffrn_standards_number         22435
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.70
_refine_diff_density_min         -2.00
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         6689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1948
_refine_ls_R_factor_gt           0.1027
_refine_ls_shift/su_max          0.0003311
_refine_ls_shift/su_mean         0.0000560
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 66.2 87.2 25.4 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2312
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.2312
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3120
_reflns_number_total             6733
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.1948
_oxford_refine_ls_scale          0.4967(11)
_oxford_reflns_number_all        6689
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '_06182015-1'
_cod_data_source_file            jp0c10074_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        4074.2(3)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C47 H36 B1 Cl3 F2 N2 O4'
_cod_database_code               1559883
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.1941(5) 0.42712(19) 0.4204(6) 0.2821 1.0000 Uani . . . . . .
C234 C 0.2007(11) 0.3603(5) 0.4317(8) 0.0802 1.0000 Uani . . . . . .
Cl3 Cl 0.0681(3) 0.33167(15) 0.3573(2) 0.0959 1.0000 Uani . . . . . .
Cl2 Cl 0.2372(4) 0.33808(19) 0.5465(2) 0.1313 1.0000 Uani . . . . . .
F1 F 0.4805(4) 0.46628(16) 0.7998(3) 0.0408 1.0000 Uani . . . . . .
B1 B 0.4750(8) 0.4114(3) 0.8134(6) 0.0378 1.0000 Uani . . . . . .
F2 F 0.3587(4) 0.39266(18) 0.7688(3) 0.0440 1.0000 Uani . . . . . .
N1 N 0.5603(6) 0.3807(2) 0.7705(4) 0.0365 1.0000 Uani . . . . . .
C4 C 0.6403(7) 0.3396(3) 0.8191(5) 0.0353 1.0000 Uani . . . . . .
C3 C 0.6983(7) 0.3198(3) 0.7567(5) 0.0389 1.0000 Uani . . . . . .
C11 C 0.7892(7) 0.2755(3) 0.7887(5) 0.0374 1.0000 Uani . . . . . .
C12 C 0.8878(7) 0.2807(3) 0.8721(6) 0.0417 1.0000 Uani . . . . . .
C13 C 0.9677(8) 0.2388(3) 0.9040(6) 0.0510 1.0000 Uani . . . . . .
C14 C 0.9507(9) 0.1906(4) 0.8525(7) 0.0563 1.0000 Uani . . . . . .
C15 C 0.8530(8) 0.1845(3) 0.7680(6) 0.0499 1.0000 Uani . . . . . .
C16 C 0.7732(7) 0.2272(3) 0.7367(6) 0.0419 1.0000 Uani . . . . . .
C2 C 0.6566(7) 0.3501(3) 0.6720(5) 0.0361 1.0000 Uani . . . . . .
C1 C 0.5694(8) 0.3873(3) 0.6822(5) 0.0424 1.0000 Uani . . . . . .
C10 C 0.4958(8) 0.4284(3) 0.6125(5) 0.0475 1.0000 Uani . . . . . .
C17 C 0.6994(7) 0.3525(3) 0.5907(5) 0.0417 1.0000 Uani . . . . . .
O2 O 0.7697(5) 0.3098(2) 0.5901(4) 0.0509 1.0000 Uani . . . . . .
C18 C 0.8270(8) 0.3114(4) 0.5161(6) 0.0518 1.0000 Uani . . . . . .
C19 C 0.9051(11) 0.2623(5) 0.5332(8) 0.0852 1.0000 Uani . . . . . .
O1 O 0.6771(6) 0.3879(3) 0.5314(4) 0.0585 1.0000 Uani . . . . . .
C5 C 0.6570(7) 0.3276(3) 0.9138(5) 0.0393 1.0000 Uani . . . . . .
C6 C 0.6048(7) 0.3580(3) 0.9667(5) 0.0401 1.0000 Uani . . . . . .
N2 N 0.5176(6) 0.3976(2) 0.9232(4) 0.0376 1.0000 Uani . . . . . .
C9 C 0.4819(7) 0.4197(3) 0.9916(6) 0.0397 1.0000 Uani . . . . . .
C8 C 0.5503(7) 0.3973(3) 1.0837(5) 0.0364 1.0000 Uani . . . . . .
C7 C 0.6232(7) 0.3577(3) 1.0674(6) 0.0392 1.0000 Uani . . . . . .
C20 C 0.7030(7) 0.3201(3) 1.1378(5) 0.0385 1.0000 Uani . . . . . .
C25 C 0.6648(8) 0.2958(3) 1.2074(5) 0.0450 1.0000 Uani . . . . . .
C24 C 0.7324(9) 0.2566(3) 1.2676(6) 0.0527 1.0000 Uani . . . . . .
C23 C 0.8418(9) 0.2401(4) 1.2623(7) 0.0607 1.0000 Uani . . . . . .
C22 C 0.8820(8) 0.2648(4) 1.1951(6) 0.0552 1.0000 Uani . . . . . .
C21 C 0.8154(8) 0.3049(3) 1.1342(6) 0.0447 1.0000 Uani . . . . . .
C26 C 0.5545(8) 0.4142(3) 1.1811(5) 0.0424 1.0000 Uani . . . . . .
O3 O 0.4722(5) 0.4148(2) 1.2110(4) 0.0448 1.0000 Uani . . . . . .
O4 O 0.6679(5) 0.4276(2) 1.2337(4) 0.0429 1.0000 Uani . . . . . .
C27 C 0.6896(8) 0.4410(4) 1.3342(6) 0.0529 1.0000 Uani . . . . . .
C28 C 0.8161(11) 0.4612(6) 1.3733(8) 0.1127 1.0000 Uani . . . . . .
C29 C 0.3833(7) 0.4591(3) 0.9642(5) 0.0393 1.0000 Uani . . . . . .
C30 C 0.3296(7) 0.4773(3) 1.0253(6) 0.0416 1.0000 Uani . . . . . .
C31 C 0.2260(7) 0.5141(3) 0.9983(6) 0.0390 1.0000 Uani . . . . . .
C32 C 0.1708(7) 0.5310(3) 0.9025(6) 0.0384 1.0000 Uani . . . . . .
C33 C 0.0694(7) 0.5625(3) 0.8760(6) 0.0419 1.0000 Uani . . . . . .
C34 C 0.0184(7) 0.5788(3) 0.9444(6) 0.0429 1.0000 Uani . . . . . .
C46 C 0.0737(7) 0.5634(3) 1.0428(6) 0.0378 1.0000 Uani . . . . . .
C44 C 0.1800(7) 0.5309(3) 1.0699(5) 0.0376 1.0000 Uani . . . . . .
C43 C 0.2311(7) 0.5173(3) 1.1698(5) 0.0402 1.0000 Uani . . . . . .
C42 C 0.1821(7) 0.5339(3) 1.2358(6) 0.0465 1.0000 Uani . . . . . .
C41 C 0.0740(7) 0.5650(3) 1.2092(6) 0.0413 1.0000 Uani . . . . . .
C45 C 0.0208(7) 0.5786(3) 1.1118(6) 0.0431 1.0000 Uani . . . . . .
C37 C -0.0897(7) 0.6098(3) 1.0815(6) 0.0442 1.0000 Uani . . . . . .
C36 C -0.1394(8) 0.6243(3) 0.9814(7) 0.0491 1.0000 Uani . . . . . .
C35 C -0.0913(8) 0.6105(3) 0.9162(6) 0.0487 1.0000 Uani . . . . . .
C38 C -0.1392(8) 0.6236(3) 1.1505(7) 0.0547 1.0000 Uani . . . . . .
C39 C -0.0870(8) 0.6094(4) 1.2446(7) 0.0568 1.0000 Uani . . . . . .
C40 C 0.0196(8) 0.5797(4) 1.2756(6) 0.0510 1.0000 Uani . . . . . .
H21 H 0.2659 0.3453 0.4103 0.1175 1.0000 Uiso R . . . . .
H121 H 0.8978 0.3131 0.9054 0.0663 1.0000 Uiso R . . . . .
H131 H 1.0355 0.2421 0.9600 0.0746 1.0000 Uiso R . . . . .
H141 H 1.0028 0.1617 0.8741 0.0750 1.0000 Uiso R . . . . .
H151 H 0.8460 0.1532 0.7325 0.0696 1.0000 Uiso R . . . . .
H161 H 0.7039 0.2227 0.6793 0.0595 1.0000 Uiso R . . . . .
H192 H 0.4826 0.4127 0.5479 0.0892 1.0000 Uiso R . . . . .
H193 H 0.5406 0.4631 0.6219 0.0897 1.0000 Uiso R . . . . .
H191 H 0.4182 0.4317 0.6237 0.0899 1.0000 Uiso R . . . . .
H221 H 0.8756 0.3441 0.5249 0.0864 1.0000 Uiso R . . . . .
H222 H 0.7635 0.3100 0.4522 0.0861 1.0000 Uiso R . . . . .
H232 H 0.9541 0.2605 0.4928 0.1400 1.0000 Uiso R . . . . .
H233 H 0.9585 0.2639 0.5994 0.1393 1.0000 Uiso R . . . . .
H231 H 0.8597 0.2301 0.5259 0.1406 1.0000 Uiso R . . . . .
H251 H 0.7070 0.2978 0.9434 0.0662 1.0000 Uiso R . . . . .
H321 H 0.5917 0.3067 1.2131 0.0653 1.0000 Uiso R . . . . .
H331 H 0.7055 0.2393 1.3136 0.0672 1.0000 Uiso R . . . . .
H341 H 0.8877 0.2136 1.3049 0.0816 1.0000 Uiso R . . . . .
H351 H 0.9554 0.2542 1.1884 0.0814 1.0000 Uiso R . . . . .
H361 H 0.8443 0.3204 1.0885 0.0725 1.0000 Uiso R . . . . .
H401 H 0.6389 0.4690 1.3445 0.0829 1.0000 Uiso R . . . . .
H402 H 0.6825 0.4087 1.3687 0.0826 1.0000 Uiso R . . . . .
H411 H 0.8421 0.4689 1.4414 0.1798 1.0000 Uiso R . . . . .
H413 H 0.8197 0.4929 1.3357 0.1803 1.0000 Uiso R . . . . .
H412 H 0.8609 0.4315 1.3622 0.1804 1.0000 Uiso R . . . . .
H421 H 0.3550 0.4729 0.8998 0.0579 1.0000 Uiso R . . . . .
H431 H 0.3621 0.4663 1.0897 0.0579 1.0000 Uiso R . . . . .
H451 H 0.2060 0.5213 0.8571 0.0631 1.0000 Uiso R . . . . .
H461 H 0.0275 0.5720 0.8113 0.0667 1.0000 Uiso R . . . . .
H501 H 0.3029 0.4959 1.1933 0.0590 1.0000 Uiso R . . . . .
H511 H 0.2176 0.5242 1.2991 0.0689 1.0000 Uiso R . . . . .
H551 H -0.2078 0.6452 0.9622 0.0698 1.0000 Uiso R . . . . .
H561 H -0.1284 0.6210 0.8529 0.0752 1.0000 Uiso R . . . . .
H571 H -0.2113 0.6438 1.1303 0.0715 1.0000 Uiso R . . . . .
H581 H -0.1225 0.6195 1.2889 0.0906 1.0000 Uiso R . . . . .
H591 H 0.0560 0.5704 1.3401 0.0779 1.0000 Uiso R . . . . .
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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . C234 . Cl3 . 109.9(7) yes
Cl1 . C234 . Cl2 . 114.3(7) yes
Cl3 . C234 . Cl2 . 111.7(6) yes
Cl1 . C234 . H21 . 110.5 no
Cl3 . C234 . H21 . 106.4 no
Cl2 . C234 . H21 . 103.8 no
F1 . B1 . F2 . 110.3(7) yes
F1 . B1 . N1 . 110.4(6) yes
F2 . B1 . N1 . 109.0(6) yes
F1 . B1 . N2 . 110.6(6) yes
F2 . B1 . N2 . 109.6(6) yes
N1 . B1 . N2 . 107.0(6) yes
B1 . N1 . C4 . 124.1(6) yes
B1 . N1 . C1 . 127.6(7) yes
C4 . N1 . C1 . 108.3(6) yes
N1 . C4 . C3 . 108.1(6) yes
N1 . C4 . C5 . 120.6(7) yes
C3 . C4 . C5 . 131.1(7) yes
C4 . C3 . C11 . 120.4(7) yes
C4 . C3 . C2 . 107.3(7) yes
C11 . C3 . C2 . 132.2(7) yes
C3 . C11 . C12 . 120.9(7) yes
C3 . C11 . C16 . 120.1(7) yes
C12 . C11 . C16 . 119.0(7) yes
C11 . C12 . C13 . 120.7(8) yes
C11 . C12 . H121 . 118.0 no
C13 . C12 . H121 . 121.3 no
C12 . C13 . C14 . 120.1(8) yes
C12 . C13 . H131 . 121.5 no
C14 . C13 . H131 . 118.4 no
C13 . C14 . C15 . 120.3(8) yes
C13 . C14 . H141 . 120.9 no
C15 . C14 . H141 . 118.7 no
C14 . C15 . C16 . 118.9(8) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 121.9 no
C11 . C16 . C15 . 121.0(8) yes
C11 . C16 . H161 . 119.8 no
C15 . C16 . H161 . 119.2 no
C3 . C2 . C1 . 107.2(6) yes
C3 . C2 . C17 . 130.1(7) yes
C1 . C2 . C17 . 122.1(7) yes
C2 . C1 . N1 . 109.0(7) yes
C2 . C1 . C10 . 129.4(7) yes
N1 . C1 . C10 . 121.6(7) yes
C1 . C10 . H192 . 105.2 no
C1 . C10 . H193 . 109.1 no
H192 . C10 . H193 . 111.8 no
C1 . C10 . H191 . 107.3 no
H192 . C10 . H191 . 110.1 no
H193 . C10 . H191 . 112.9 no
C2 . C17 . O2 . 111.6(7) yes
C2 . C17 . O1 . 125.4(7) yes
O2 . C17 . O1 . 123.0(7) yes
C17 . O2 . C18 . 115.5(6) yes
O2 . C18 . C19 . 105.8(7) yes
O2 . C18 . H221 . 109.1 no
C19 . C18 . H221 . 110.0 no
O2 . C18 . H222 . 108.3 no
C19 . C18 . H222 . 111.0 no
H221 . C18 . H222 . 112.4 no
C18 . C19 . H232 . 113.8 no
C18 . C19 . H233 . 107.0 no
H232 . C19 . H233 . 107.6 no
C18 . C19 . H231 . 111.3 no
H232 . C19 . H231 . 109.5 no
H233 . C19 . H231 . 107.5 no
C4 . C5 . C6 . 121.8(7) yes
C4 . C5 . H251 . 118.8 no
C6 . C5 . H251 . 119.4 no
C5 . C6 . N2 . 121.5(7) yes
C5 . C6 . C7 . 130.8(8) yes
N2 . C6 . C7 . 107.8(6) yes
B1 . N2 . C6 . 123.4(6) yes
B1 . N2 . C9 . 128.5(6) yes
C6 . N2 . C9 . 108.1(6) yes
N2 . C9 . C8 . 109.6(7) yes
N2 . C9 . C29 . 119.4(7) yes
C8 . C9 . C29 . 130.9(7) yes
C9 . C8 . C7 . 107.0(7) yes
C9 . C8 . C26 . 129.2(7) yes
C7 . C8 . C26 . 123.7(7) yes
C6 . C7 . C8 . 107.4(7) yes
C6 . C7 . C20 . 124.8(7) yes
C8 . C7 . C20 . 127.8(7) yes
C7 . C20 . C25 . 119.9(7) yes
C7 . C20 . C21 . 122.1(7) yes
C25 . C20 . C21 . 117.9(7) yes
C20 . C25 . C24 . 121.0(8) yes
C20 . C25 . H321 . 119.1 no
C24 . C25 . H321 . 119.9 no
C25 . C24 . C23 . 121.4(8) yes
C25 . C24 . H331 . 121.1 no
C23 . C24 . H331 . 117.5 no
C24 . C23 . C22 . 118.2(8) yes
C24 . C23 . H341 . 120.2 no
C22 . C23 . H341 . 121.6 no
C23 . C22 . C21 . 121.3(9) yes
C23 . C22 . H351 . 120.8 no
C21 . C22 . H351 . 117.9 no
C20 . C21 . C22 . 120.2(8) yes
C20 . C21 . H361 . 120.5 no
C22 . C21 . H361 . 119.3 no
C8 . C26 . O3 . 126.8(8) yes
C8 . C26 . O4 . 108.9(7) yes
O3 . C26 . O4 . 124.3(7) yes
C26 . O4 . C27 . 115.9(6) yes
O4 . C27 . C28 . 105.8(7) yes
O4 . C27 . H401 . 115.0 no
C28 . C27 . H401 . 107.4 no
O4 . C27 . H402 . 109.7 no
C28 . C27 . H402 . 109.2 no
H401 . C27 . H402 . 109.6 no
C27 . C28 . H411 . 112.8 no
C27 . C28 . H413 . 106.4 no
H411 . C28 . H413 . 112.3 no
C27 . C28 . H412 . 103.0 no
H411 . C28 . H412 . 109.5 no
H413 . C28 . H412 . 112.5 no
C9 . C29 . C30 . 123.5(7) yes
C9 . C29 . H421 . 118.9 no
C30 . C29 . H421 . 117.6 no
C29 . C30 . C31 . 124.6(7) yes
C29 . C30 . H431 . 117.3 no
C31 . C30 . H431 . 118.1 no
C30 . C31 . C32 . 121.0(7) yes
C30 . C31 . C44 . 118.8(7) yes
C32 . C31 . C44 . 120.2(7) yes
C31 . C32 . C33 . 121.1(7) yes
C31 . C32 . H451 . 118.6 no
C33 . C32 . H451 . 120.3 no
C32 . C33 . C34 . 120.6(7) yes
C32 . C33 . H461 . 122.4 no
C34 . C33 . H461 . 116.9 no
C33 . C34 . C46 . 119.8(7) yes
C33 . C34 . C35 . 120.9(7) yes
C46 . C34 . C35 . 119.3(8) yes
C34 . C46 . C44 . 119.2(7) yes
C34 . C46 . C45 . 119.9(7) yes
C44 . C46 . C45 . 120.8(7) yes
C46 . C44 . C31 . 119.1(7) yes
C46 . C44 . C43 . 116.2(7) yes
C31 . C44 . C43 . 124.7(7) yes
C44 . C43 . C42 . 122.3(8) yes
C44 . C43 . H501 . 120.8 no
C42 . C43 . H501 . 116.8 no
C43 . C42 . C41 . 122.0(8) yes
C43 . C42 . H511 . 119.6 no
C41 . C42 . H511 . 118.4 no
C42 . C41 . C45 . 117.2(7) yes
C42 . C41 . C40 . 122.3(8) yes
C45 . C41 . C40 . 120.4(8) yes
C46 . C45 . C41 . 121.3(7) yes
C46 . C45 . C37 . 119.6(7) yes
C41 . C45 . C37 . 119.1(7) yes
C45 . C37 . C36 . 117.2(7) yes
C45 . C37 . C38 . 118.1(8) yes
C36 . C37 . C38 . 124.7(8) yes
C37 . C36 . C35 . 124.0(8) yes
C37 . C36 . H551 . 117.7 no
C35 . C36 . H551 . 118.4 no
C34 . C35 . C36 . 119.9(8) yes
C34 . C35 . H561 . 120.6 no
C36 . C35 . H561 . 119.4 no
C37 . C38 . C39 . 122.1(9) yes
C37 . C38 . H571 . 117.7 no
C39 . C38 . H571 . 120.2 no
C38 . C39 . C40 . 120.9(8) yes
C38 . C39 . H581 . 119.8 no
C40 . C39 . H581 . 119.3 no
C39 . C40 . C41 . 119.4(8) yes
C39 . C40 . H591 . 121.1 no
C41 . C40 . H591 . 119.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C234 . 1.654(12) yes
C234 . Cl3 . 1.735(11) yes
C234 . Cl2 . 1.693(11) yes
C234 . H21 . 1.004 no
F1 . B1 . 1.371(9) yes
B1 . F2 . 1.392(10) yes
B1 . N1 . 1.564(10) yes
B1 . N2 . 1.564(10) yes
N1 . C4 . 1.409(9) yes
N1 . C1 . 1.357(9) yes
C4 . C3 . 1.415(10) yes
C4 . C5 . 1.378(10) yes
C3 . C11 . 1.495(10) yes
C3 . C2 . 1.396(10) yes
C11 . C12 . 1.386(10) yes
C11 . C16 . 1.394(10) yes
C12 . C13 . 1.372(11) yes
C12 . H121 . 0.926 no
C13 . C14 . 1.388(12) yes
C13 . H131 . 0.940 no
C14 . C15 . 1.392(12) yes
C14 . H141 . 0.927 no
C15 . C16 . 1.385(11) yes
C15 . H151 . 0.922 no
C16 . H161 . 0.966 no
C2 . C1 . 1.430(10) yes
C2 . C17 . 1.459(10) yes
C1 . C10 . 1.495(10) yes
C10 . H192 . 0.992 no
C10 . H193 . 0.993 no
C10 . H191 . 0.996 no
C17 . O2 . 1.346(9) yes
C17 . O1 . 1.200(9) yes
O2 . C18 . 1.474(9) yes
C18 . C19 . 1.495(12) yes
C18 . H221 . 0.974 no
C18 . H222 . 0.988 no
C19 . H232 . 0.967 no
C19 . H233 . 0.969 no
C19 . H231 . 0.945 no
C5 . C6 . 1.376(10) yes
C5 . H251 . 0.952 no
C6 . N2 . 1.409(10) yes
C6 . C7 . 1.430(10) yes
N2 . C9 . 1.341(9) yes
C9 . C8 . 1.437(10) yes
C9 . C29 . 1.468(11) yes
C8 . C7 . 1.380(10) yes
C8 . C26 . 1.484(10) yes
C7 . C20 . 1.472(10) yes
C20 . C25 . 1.396(11) yes
C20 . C21 . 1.407(11) yes
C25 . C24 . 1.371(11) yes
C25 . H321 . 0.940 no
C24 . C23 . 1.391(13) yes
C24 . H331 . 0.947 no
C23 . C22 . 1.382(13) yes
C23 . H341 . 0.942 no
C22 . C21 . 1.388(11) yes
C22 . H351 . 0.949 no
C21 . H361 . 0.939 no
C26 . O3 . 1.205(10) yes
C26 . O4 . 1.348(10) yes
O4 . C27 . 1.457(9) yes
C27 . C28 . 1.501(14) yes
C27 . H401 . 0.963 no
C27 . H402 . 0.965 no
C28 . H411 . 0.966 no
C28 . H413 . 0.968 no
C28 . H412 . 0.951 no
C29 . C30 . 1.349(11) yes
C29 . H421 . 0.959 no
C30 . C31 . 1.470(11) yes
C30 . H431 . 0.938 no
C31 . C32 . 1.405(10) yes
C31 . C44 . 1.410(10) yes
C32 . C33 . 1.374(10) yes
C32 . H451 . 0.936 no
C33 . C34 . 1.405(11) yes
C33 . H461 . 0.944 no
C34 . C46 . 1.428(11) yes
C34 . C35 . 1.455(11) yes
C46 . C44 . 1.432(10) yes
C46 . C45 . 1.423(10) yes
C44 . C43 . 1.432(10) yes
C43 . C42 . 1.361(10) yes
C43 . H501 . 0.961 no
C42 . C41 . 1.431(11) yes
C42 . H511 . 0.918 no
C41 . C45 . 1.401(11) yes
C41 . C40 . 1.398(11) yes
C45 . C37 . 1.455(11) yes
C37 . C36 . 1.439(12) yes
C37 . C38 . 1.384(12) yes
C36 . C35 . 1.323(12) yes
C36 . H551 . 0.921 no
C35 . H561 . 0.925 no
C38 . C39 . 1.362(13) yes
C38 . H571 . 0.947 no
C39 . C40 . 1.399(12) yes
C39 . H581 . 0.927 no
C40 . H591 . 0.930 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C15 . H151 . O3 4_554 137.8(3) 0.922 2.343 3.088(12) yes
C27 . H402 . O1 1_556 136.0(3) 0.965 2.484 3.248(12) yes
C30 . H431 . C26 . 131.6(2) 0.938 2.566 3.265(12) yes
C30 . H431 . O3 . 155.6(2) 0.938 2.220 3.099(12) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-10 10 3 x .
-8 13 2 x .
-9 2 4 x .
-9 1 4 x .
-11 3 7 x .
-11 3 7 x .
3 16 7 x .
-9 1 12 x .
0 8 12 x .
-5 23 6 x .
3 16 7 x .
0 26 0 x .
