#------------------------------------------------------------------------------
#$Date: 2017-12-05 01:29:37 +0200 (Tue, 05 Dec 2017) $
#$Revision: 203945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/83/1548378.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_1548378
loop_
_publ_author_name
'Gurinov, Andrei A.'
'Denisov, Gleb S.'
'Borissova, Alexandra O.'
'Goloveshkin, Alexander S.'
'Greindl, Julian'
'Limbach, Hans-Heinrich'
'Shenderovich, Ilya G.'
_publ_section_title
;
 NMR Study of Solvation Effect on the Geometry of Proton-Bound Homodimers
 of Increasing Size.
;
_journal_issue                   45
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              8697
_journal_page_last               8705
_journal_paper_doi               10.1021/acs.jpca.7b09285
_journal_volume                  121
_journal_year                    2017
_chemical_formula_moiety
'C32 H12 B F24, C13 H10 N, C13 H9 N, 2(C H Cl3)'
_chemical_formula_sum            'C60 H33 B Cl6 F24 N2'
_chemical_formula_weight         1461.39
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 124.4790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.4747(14)
_cell_length_b                   18.1680(10)
_cell_length_c                   17.2650(18)
_cell_measurement_reflns_used    5667
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.47
_cell_volume                     6069.8(8)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19909
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.54
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0844 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.8816.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2920
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.627
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8066
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1032P)²+22.4746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2147
_reflns_number_gt                5832
_reflns_number_total             8066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp7b09285_si_002.cif
_cod_data_source_block           a
_cod_database_code               1548378
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1S(H1S)
3.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C27(H27), C19(H19), C16(H16), C3(H3), C7(H7), C4(H4),
 C6(H6), C5(H5), C30(H30), C10(H10), C13(H13), C11(H11), C14(H14), C12(H12)
;
_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+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
B1 B 0.0000 0.7436(2) 0.2500 0.0157(7) Uani 1 d . . 2 S T P
C15 C 0.06333(12) 0.79806(13) 0.32526(17) 0.0161(4) Uani 1 d . . 1 . . .
C22 C 0.05315(12) 0.84354(14) 0.38219(17) 0.0179(5) Uani 1 d . . 1 . . .
H22 H 0.0104 0.8427 0.3739 0.022 Uiso 1 calc . . 1 R . .
C23 C 0.02088(12) 0.69005(13) 0.19354(17) 0.0157(4) Uani 1 d A . 1 . . .
C17 C 0.17943(12) 0.84971(14) 0.40773(18) 0.0196(5) Uani 1 d . . 1 . . .
C24 C 0.08231(12) 0.64910(13) 0.24076(17) 0.0173(5) Uani 1 d . . 1 . . .
H24 H 0.1112 0.6516 0.3060 0.021 Uiso 1 calc . . 1 R . .
C28 C -0.00303(13) 0.63460(14) 0.04855(18) 0.0193(5) Uani 1 d A . 1 . . .
C25 C 0.10151(12) 0.60487(14) 0.19350(18) 0.0190(5) Uani 1 d . . 1 . . .
C27 C 0.05958(13) 0.59715(15) 0.09653(18) 0.0208(5) Uani 1 d . . 1 . . .
H27 H 0.0728 0.5681 0.0650 0.025 Uiso 1 calc . . 1 R . .
C20 C 0.10414(13) 0.88948(14) 0.45007(18) 0.0203(5) Uani 1 d B . 1 . . .
C19 C 0.16874(13) 0.89315(14) 0.46426(18) 0.0219(5) Uani 1 d . . 1 . . .
H19 H 0.2034 0.9237 0.5100 0.026 Uiso 1 calc . . 1 R . .
C1 C 0.05122(13) 0.63651(15) -0.1730(2) 0.0232(5) Uani 1 d . . 1 . . .
C16 C 0.12781(12) 0.80398(13) 0.33887(17) 0.0171(4) Uani 1 d . . 1 . . .
H16 H 0.1365 0.7767 0.3010 0.021 Uiso 1 calc . . 1 R . .
C18 C 0.24749(13) 0.85285(15) 0.4187(2) 0.0259(6) Uani 1 d . . 1 . . .
C29 C -0.05090(14) 0.62885(17) -0.0560(2) 0.0268(6) Uani 1 d . . 1 . . .
C26 C 0.17104(13) 0.56840(16) 0.24912(19) 0.0235(5) Uani 1 d . . 1 . . .
C21 C 0.08829(15) 0.93516(16) 0.50801(19) 0.0275(6) Uani 1 d . . 1 . . .
C3 C 0.0000 0.5203(2) -0.2500 0.0304(9) Uani 1 d . . 2 S T P
H3 H 0.0000 0.4691 -0.2500 0.036 Uiso 1 calc . . 2 RS T P
C2 C 0.05234(15) 0.55803(16) -0.1716(2) 0.0274(6) Uani 1 d . . 1 . . .
C7 C 0.10311(15) 0.67675(18) -0.0938(2) 0.0296(6) Uani 1 d . . 1 . . .
H7 H 0.1021 0.7279 -0.0942 0.035 Uiso 1 calc . . 1 R . .
C4 C 0.10678(18) 0.52201(19) -0.0890(3) 0.0381(8) Uani 1 d . . 1 . . .
H4 H 0.1080 0.4709 -0.0861 0.046 Uiso 1 calc . . 1 R . .
C6 C 0.15473(17) 0.6396(2) -0.0170(2) 0.0384(7) Uani 1 d . . 1 . . .
H6 H 0.1892 0.6660 0.0348 0.046 Uiso 1 calc . . 1 R . .
C5 C 0.15673(18) 0.5615(2) -0.0148(2) 0.0414(8) Uani 1 d . . 1 . . .
H5 H 0.1926 0.5373 0.0380 0.050 Uiso 1 calc . . 1 R . .
C30 C -0.02168(12) 0.67994(13) 0.09566(17) 0.0169(4) Uani 1 d . . 1 . . .
H30 H -0.0638 0.7044 0.0612 0.020 Uiso 1 calc A . 1 R . .
N1 N 0.0000 0.67206(18) -0.2500 0.0216(6) Uani 1 d . . 2 DS T P
F8 F 0.18144(9) 0.52172(12) 0.19842(14) 0.0402(5) Uani 1 d . . 1 . . .
F11 F -0.03351(9) 0.57598(11) -0.09248(12) 0.0361(4) Uani 1 d A . 1 . . .
F3 F 0.26551(9) 0.78946(10) 0.40071(16) 0.0402(5) Uani 1 d . . 1 . . .
F9 F 0.22250(9) 0.61797(11) 0.28527(16) 0.0409(5) Uani 1 d . . 1 . . .
F7 F 0.18215(10) 0.53067(11) 0.32304(14) 0.0404(5) Uani 1 d . . 1 . . .
F4 F 0.14458(10) 0.96748(11) 0.58131(13) 0.0378(4) Uani 1 d B . 1 . . .
F1 F 0.29944(9) 0.87238(15) 0.50527(16) 0.0532(6) Uani 1 d . . 1 . . .
F2 F 0.24691(11) 0.90243(12) 0.36038(18) 0.0504(6) Uani 1 d . . 1 . . .
F5 F 0.04403(12) 0.98925(13) 0.45836(14) 0.0507(6) Uani 1 d B . 1 . . .
F10 F -0.11508(9) 0.61431(17) -0.08360(14) 0.0602(8) Uani 1 d A 1 1 . . .
F6 F 0.05985(12) 0.89567(12) 0.54288(15) 0.0464(5) Uani 1 d B 1 1 . . .
F12 F -0.05244(15) 0.69064(13) -0.09887(14) 0.0594(7) Uani 1 d A 1 1 . . .
C8 C 0.05223(13) 0.86132(15) -0.24339(17) 0.0203(5) Uani 1 d . . 1 . . .
C9 C 0.05460(14) 0.93997(16) -0.24144(18) 0.0237(5) Uani 1 d . . 1 . . .
C10 C 0.0000 0.9780(2) -0.2500 0.0262(8) Uani 1 d . . 2 S T P
H10 H 0.0000 1.0292 -0.2500 0.031 Uiso 1 calc . . 2 RS T P
C13 C 0.16105(15) 0.85905(19) -0.2282(2) 0.0317(6) Uani 1 d . . 1 . . .
H13 H 0.1966 0.8328 -0.2243 0.038 Uiso 1 calc . . 1 R . .
C11 C 0.11204(16) 0.97640(17) -0.2317(2) 0.0295(6) Uani 1 d . . 1 . . .
H11 H 0.1140 1.0275 -0.2302 0.035 Uiso 1 calc . . 1 R . .
C14 C 0.10695(14) 0.82173(17) -0.23715(19) 0.0254(5) Uani 1 d . . 1 . . .
H14 H 0.1060 0.7706 -0.2392 0.030 Uiso 1 calc . . 1 R . .
C12 C 0.16383(16) 0.9370(2) -0.2246(2) 0.0338(7) Uani 1 d . . 1 . . .
H12 H 0.2014 0.9613 -0.2174 0.041 Uiso 1 calc . . 1 R . .
N2 N 0.0000 0.82362(18) -0.2500 0.0203(6) Uani 1 d . . 2 S T P
Cl2S Cl 0.12806(12) 0.80202(14) 0.10629(14) 0.1186(7) Uani 1 d . . 1 . . .
Cl1S Cl 0.27267(9) 0.83085(11) 0.19023(11) 0.0996(6) Uani 1 d . . 1 . . .
Cl3S Cl 0.17383(7) 0.87250(8) 0.00068(8) 0.0711(4) Uani 1 d . . 1 . . .
C1S C 0.1870(3) 0.8618(2) 0.1101(3) 0.0581(12) Uani 1 d . . 1 . . .
H1S H 0.1821 0.9101 0.1311 0.070 Uiso 1 calc . . 1 R . .
H1 H 0.0000 0.7190(11) -0.2500 0.070 Uiso 1 d . . 2 DRS T P
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C15 B1 C15 105.8(3) 2 .
C23 B1 C15 112.81(11) 2 2
C23 B1 C15 112.81(11) . .
C23 B1 C15 109.24(12) 2 .
C23 B1 C15 109.24(12) . 2
C23 B1 C23 107.0(3) . 2
C22 C15 B1 118.18(19) . .
C16 C15 B1 126.1(2) . .
C16 C15 C22 115.7(2) . .
C15 C22 H22 118.7 . .
C20 C22 C15 122.6(2) . .
C20 C22 H22 118.7 . .
C24 C23 B1 121.70(19) . .
C24 C23 C30 115.3(2) . .
C30 C23 B1 123.02(19) . .
C19 C17 C16 121.6(2) . .
C19 C17 C18 119.6(2) . .
C16 C17 C18 118.7(2) . .
C23 C24 H24 118.9 . .
C25 C24 C23 122.3(2) . .
C25 C24 H24 118.9 . .
C27 C28 C29 120.3(2) . .
C27 C28 C30 121.2(2) . .
C30 C28 C29 118.5(2) . .
C24 C25 C26 118.5(2) . .
C27 C25 C24 121.5(2) . .
C27 C25 C26 120.0(2) . .
C28 C27 H27 121.4 . .
C25 C27 C28 117.3(2) . .
C25 C27 H27 121.4 . .
C22 C20 C19 120.7(2) . .
C22 C20 C21 118.5(2) . .
C19 C20 C21 120.8(2) . .
C17 C19 C20 117.5(2) . .
C17 C19 H19 121.2 . .
C20 C19 H19 121.2 . .
C7 C1 C2 120.2(3) . .
N1 C1 C2 119.5(3) . .
N1 C1 C7 120.3(3) . .
C15 C16 H16 119.2 . .
C17 C16 C15 121.7(2) . .
C17 C16 H16 119.2 . .
F3 C18 C17 113.4(2) . .
F3 C18 F1 106.5(2) . .
F3 C18 F2 106.0(3) . .
F1 C18 C17 112.6(2) . .
F1 C18 F2 106.0(2) . .
F2 C18 C17 111.9(2) . .
F11 C29 C28 113.5(2) . .
F11 C29 F12 105.3(2) . .
F10 C29 C28 111.9(2) . .
F10 C29 F11 106.1(2) . .
F10 C29 F12 107.5(3) . .
F12 C29 C28 112.1(2) . .
F8 C26 C25 113.4(2) . .
F8 C26 F9 106.2(2) . .
F8 C26 F7 106.9(2) . .
F9 C26 C25 111.6(2) . .
F7 C26 C25 113.0(2) . .
F7 C26 F9 105.2(2) . .
F4 C21 C20 112.8(2) . .
F5 C21 C20 112.1(2) . .
F5 C21 F4 106.1(2) . .
F5 C21 F6 106.3(3) . .
F6 C21 C20 112.3(2) . .
F6 C21 F4 106.7(2) . .
C2 C3 H3 119.6 2_554 .
C2 C3 H3 119.6 . .
C2 C3 C2 120.9(4) . 2_554
C3 C2 C1 118.6(3) . .
C3 C2 C4 123.1(3) . .
C4 C2 C1 118.3(3) . .
C1 C7 H7 120.4 . .
C6 C7 C1 119.3(3) . .
C6 C7 H7 120.4 . .
C2 C4 H4 119.7 . .
C5 C4 C2 120.6(3) . .
C5 C4 H4 119.7 . .
C7 C6 H6 119.4 . .
C7 C6 C5 121.2(3) . .
C5 C6 H6 119.4 . .
C4 C5 C6 120.5(3) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C23 C30 H30 118.8 . .
C28 C30 C23 122.4(2) . .
C28 C30 H30 118.8 . .
C1 N1 C1 122.8(3) 2_554 .
C1 N1 H1 118.59(17) 2_554 .
C1 N1 H1 118.59(17) . .
C14 C8 C9 118.8(2) . .
N2 C8 C9 122.0(2) . .
N2 C8 C14 119.2(3) . .
C10 C9 C8 118.3(3) . .
C10 C9 C11 122.5(3) . .
C11 C9 C8 119.3(3) . .
C9 C10 C9 120.3(4) . 2_554
C9 C10 H10 119.9 . .
C9 C10 H10 119.9 2_554 .
C14 C13 H13 119.4 . .
C14 C13 C12 121.1(3) . .
C12 C13 H13 119.4 . .
C9 C11 H11 119.8 . .
C12 C11 C9 120.4(3) . .
C12 C11 H11 119.8 . .
C8 C14 H14 120.1 . .
C13 C14 C8 119.9(3) . .
C13 C14 H14 120.1 . .
C13 C12 H12 119.8 . .
C11 C12 C13 120.4(3) . .
C11 C12 H12 119.8 . .
C8 N2 C8 119.1(3) . 2_554
Cl2S C1S Cl1S 111.1(2) . .
Cl2S C1S Cl3S 112.4(3) . .
Cl2S C1S H1S 108.4 . .
Cl1S C1S H1S 108.4 . .
Cl3S C1S Cl1S 108.0(3) . .
Cl3S C1S H1S 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C15 1.640(3) .
B1 C15 1.640(3) 2
B1 C23 1.637(3) 2
B1 C23 1.637(3) .
C15 C22 1.404(3) .
C15 C16 1.399(3) .
C22 H22 0.9300 .
C22 C20 1.384(4) .
C23 C24 1.402(3) .
C23 C30 1.406(3) .
C17 C19 1.384(4) .
C17 C16 1.393(3) .
C17 C18 1.500(3) .
C24 H24 0.9300 .
C24 C25 1.390(3) .
C28 C27 1.390(3) .
C28 C29 1.495(4) .
C28 C30 1.391(3) .
C25 C27 1.388(4) .
C25 C26 1.500(3) .
C27 H27 0.9300 .
C20 C19 1.394(4) .
C20 C21 1.500(4) .
C19 H19 0.9300 .
C1 C2 1.426(4) .
C1 C7 1.414(4) .
C1 N1 1.349(3) .
C16 H16 0.9300 .
C18 F3 1.323(3) .
C18 F1 1.335(3) .
C18 F2 1.346(4) .
C29 F11 1.333(3) .
C29 F10 1.324(3) .
C29 F12 1.334(4) .
C26 F8 1.337(3) .
C26 F9 1.344(3) .
C26 F7 1.338(3) .
C21 F4 1.341(3) .
C21 F5 1.331(4) .
C21 F6 1.333(4) .
C3 H3 0.9300 .
C3 C2 1.389(4) .
C3 C2 1.389(4) 2_554
C2 C4 1.425(4) .
C7 H7 0.9300 .
C7 C6 1.365(4) .
C4 H4 0.9300 .
C4 C5 1.353(6) .
C6 H6 0.9300 .
C6 C5 1.420(6) .
C5 H5 0.9300 .
C30 H30 0.9300 .
N1 C1 1.349(3) 2_554
N1 H1 0.85(2) .
C8 C9 1.430(4) .
C8 C14 1.422(4) .
C8 N2 1.352(3) .
C9 C10 1.389(3) .
C9 C11 1.424(4) .
C10 C9 1.389(3) 2_554
C10 H10 0.9300 .
C13 H13 0.9300 .
C13 C14 1.369(4) .
C13 C12 1.418(5) .
C11 H11 0.9300 .
C11 C12 1.355(5) .
C14 H14 0.9300 .
C12 H12 0.9300 .
N2 C8 1.352(3) 2_554
Cl2S C1S 1.731(6) .
Cl1S C1S 1.767(5) .
Cl3S C1S 1.744(4) .
C1S H1S 0.9800 .
