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#$Date: 2023-04-27 18:28:39 +0300 (Thu, 27 Apr 2023) $
#$Revision: 282882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/16/7051631.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_7051631
loop_
_publ_author_name
'Galbraith, Ewan'
'Kelly, Andrew M.'
'Fossey, John S.'
'Kociok-Köhn, Gabriele'
'Davidson, Matthew G.'
'Bull, Steven D.'
'James, Tony D.'
_publ_section_title
;
 Dynamic covalent self-assembled macrocycles prepared from
 2-formyl-aryl-boronic acids and 1,2-amino alcohols
;
_journal_issue                   1
_journal_name_full               'New J. Chem.'
_journal_page_first              181
_journal_page_last               185
_journal_paper_doi               10.1039/B815138E
_journal_volume                  33
_journal_year                    2009
_chemical_formula_sum            'C27 H31 B2 Cl3 N2 O3'
_chemical_formula_weight         559.51
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.1380(10)
_cell_angle_beta                 110.4610(10)
_cell_angle_gamma                106.6310(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5230(2)
_cell_length_b                   11.6200(3)
_cell_length_c                   13.0520(4)
_cell_measurement_reflns_used    15563
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1371.87(6)
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
DENZO-SCALEPACK Z. Otwinowski and W. Minor, "
Processing of X-ray Diffraction Data Collected in Oscillation Mode ",
Methods in Enzymology, Volume 276: Macromolecular Crystallography,
part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
'WinGX publication routines, Farrugia,
L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
SHELXL97 -Program for Crystal Structure Analysis (Release 97-2).
Sheldrick, G.M., Institüt für Anorganische Chemie der Universität,
Tammanstrasse 4, D-3400 Göttingen, Germany, 1998
;
_computing_structure_solution
;
SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. ,
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
(1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19446
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²+1.0894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                4946
_reflns_number_total             6273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B815138E.txt
_cod_data_source_block           k07tdj7
_cod_database_code               7051631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.96735(15) -0.03791(13) 0.83987(11) 0.0199(3) Uani 1 1 d . . .
N2 N 0.68811(15) 0.12398(13) 0.63385(12) 0.0197(3) Uani 1 1 d . . .
O1 O 0.70679(13) -0.08065(11) 0.63588(10) 0.0217(3) Uani 1 1 d . . .
O2 O 0.86310(13) 0.12194(12) 0.86703(10) 0.0231(3) Uani 1 1 d . . .
O3 O 0.93481(12) 0.10217(11) 0.70777(9) 0.0201(2) Uani 1 1 d . . .
B1 B 0.7878(2) 0.03699(18) 0.62396(16) 0.0201(4) Uani 1 1 d . . .
B2 B 0.9678(2) 0.10296(18) 0.82362(16) 0.0206(4) Uani 1 1 d . . .
C1 C 0.77258(18) -0.17091(16) 0.65252(14) 0.0209(3) Uani 1 1 d . . .
H1 H 0.8489 -0.1576 0.6220 0.025 Uiso 1 1 calc R . .
C2 C 0.6522(2) -0.30012(17) 0.58707(16) 0.0273(4) Uani 1 1 d . . .
H2A H 0.5685 -0.3052 0.6068 0.033 Uiso 1 1 calc R . .
H2B H 0.6183 -0.3095 0.5042 0.033 Uiso 1 1 calc R . .
C3 C 0.7003(2) -0.40861(17) 0.61196(17) 0.0302(4) Uani 1 1 d . . .
H3A H 0.6166 -0.4892 0.5698 0.036 Uiso 1 1 calc R . .
H3B H 0.7778 -0.4094 0.5859 0.036 Uiso 1 1 calc R . .
C4 C 0.7571(2) -0.39442(18) 0.73912(17) 0.0306(4) Uani 1 1 d . . .
H4A H 0.7897 -0.4642 0.7550 0.037 Uiso 1 1 calc R . .
H4B H 0.6779 -0.3983 0.7643 0.037 Uiso 1 1 calc R . .
C5 C 0.8844(2) -0.26962(17) 0.80526(15) 0.0262(4) Uani 1 1 d . . .
H5A H 0.9663 -0.2692 0.7843 0.031 Uiso 1 1 calc R . .
H5B H 0.9183 -0.2608 0.8881 0.031 Uiso 1 1 calc R . .
C6 C 0.84229(18) -0.15824(16) 0.78095(14) 0.0206(3) Uani 1 1 d . . .
H6 H 0.7679 -0.1552 0.8113 0.025 Uiso 1 1 calc R . .
C7 C 1.09274(19) -0.02814(17) 0.91170(14) 0.0229(4) Uani 1 1 d . . .
H7 H 1.1130 -0.0976 0.9332 0.027 Uiso 1 1 calc R . .
C8 C 1.20110(19) 0.09898(17) 0.95727(14) 0.0226(4) Uani 1 1 d . . .
C9 C 1.3462(2) 0.13634(19) 1.03462(15) 0.0282(4) Uani 1 1 d . . .
H9 H 1.3839 0.0775 1.0638 0.034 Uiso 1 1 calc R . .
C10 C 1.4338(2) 0.2622(2) 1.06765(16) 0.0321(4) Uani 1 1 d . . .
H10 H 1.5332 0.2909 1.1203 0.039 Uiso 1 1 calc R . .
C11 C 1.3756(2) 0.34625(19) 1.02344(16) 0.0310(4) Uani 1 1 d . . .
H11 H 1.4361 0.4324 1.0467 0.037 Uiso 1 1 calc R . .
C12 C 1.2302(2) 0.30658(18) 0.94565(15) 0.0278(4) Uani 1 1 d . . .
H12 H 1.1931 0.3657 0.9164 0.033 Uiso 1 1 calc R . .
C13 C 1.13915(19) 0.18140(17) 0.91058(14) 0.0225(3) Uani 1 1 d . . .
C14 C 0.80725(19) 0.21710(16) 0.84357(14) 0.0215(3) Uani 1 1 d . . .
H14 H 0.8800 0.2853 0.8326 0.026 Uiso 1 1 calc R . .
C15 C 0.7836(2) 0.26925(18) 0.94771(15) 0.0278(4) Uani 1 1 d . . .
H15A H 0.7249 0.1986 0.9654 0.033 Uiso 1 1 calc R . .
H15B H 0.8796 0.3110 1.0141 0.033 Uiso 1 1 calc R . .
C16 C 0.7072(2) 0.36244(19) 0.93149(16) 0.0300(4) Uani 1 1 d . . .
H16A H 0.6930 0.3911 1.0009 0.036 Uiso 1 1 calc R . .
H16B H 0.7680 0.4366 0.9190 0.036 Uiso 1 1 calc R . .
C17 C 0.5602(2) 0.2999(2) 0.82915(17) 0.0345(5) Uani 1 1 d . . .
H17A H 0.5109 0.3607 0.8177 0.041 Uiso 1 1 calc R . .
H17B H 0.4977 0.2286 0.8437 0.041 Uiso 1 1 calc R . .
C18 C 0.5797(2) 0.25275(18) 0.72160(15) 0.0268(4) Uani 1 1 d . . .
H18A H 0.6339 0.3254 0.7032 0.032 Uiso 1 1 calc R . .
H18B H 0.4825 0.2092 0.6568 0.032 Uiso 1 1 calc R . .
C19 C 0.66218(18) 0.16293(16) 0.73564(14) 0.0203(3) Uani 1 1 d . . .
H19 H 0.5988 0.0857 0.7439 0.024 Uiso 1 1 calc R . .
C20 C 0.63634(18) 0.15143(16) 0.54019(14) 0.0228(4) Uani 1 1 d . . .
H20 H 0.5762 0.1998 0.5290 0.027 Uiso 1 1 calc R . .
C21 C 0.67840(18) 0.10151(17) 0.45276(14) 0.0230(4) Uani 1 1 d . . .
C22 C 0.6408(2) 0.11741(19) 0.34377(15) 0.0296(4) Uani 1 1 d . . .
H22 H 0.5809 0.1638 0.3185 0.036 Uiso 1 1 calc R . .
C23 C 0.6938(2) 0.0634(2) 0.27349(16) 0.0346(5) Uani 1 1 d . . .
H23 H 0.6717 0.0739 0.1993 0.042 Uiso 1 1 calc R . .
C24 C 0.7792(2) -0.0062(2) 0.31102(16) 0.0330(4) Uani 1 1 d . . .
H24 H 0.8133 -0.0442 0.2615 0.040 Uiso 1 1 calc R . .
C25 C 0.8155(2) -0.02097(18) 0.42061(15) 0.0269(4) Uani 1 1 d . . .
H25 H 0.8737 -0.0690 0.4449 0.032 Uiso 1 1 calc R . .
C26 C 0.76679(18) 0.03425(16) 0.49407(14) 0.0221(3) Uani 1 1 d . . .
C30 C 1.0787(2) 0.3577(2) 0.6508(2) 0.0404(5) Uani 1 1 d . . .
H30 H 1.0474 0.2764 0.6687 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.99856(8) 0.33121(8) 0.50337(6) 0.0752(3) Uani 1 1 d . . .
Cl2 Cl 1.26798(8) 0.41578(11) 0.69867(8) 0.0872(3) Uani 1 1 d . . .
Cl3 Cl 1.02555(12) 0.46361(9) 0.71987(8) 0.0834(3) Uani 1 1 d . . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
C7 N1 C6 123.20(15) . . ?
C7 N1 B2 110.84(14) . . ?
C6 N1 B2 125.95(13) . . ?
C20 N2 C19 124.68(15) . . ?
C20 N2 B1 110.58(14) . . ?
C19 N2 B1 124.75(13) . . ?
C1 O1 B1 118.77(13) . . ?
C14 O2 B2 119.36(13) . . ?
B2 O3 B1 118.88(14) . . ?
O3 B1 O1 116.68(14) . . ?
O3 B1 C26 114.09(15) . . ?
O1 B1 C26 114.68(14) . . ?
O3 B1 N2 109.42(13) . . ?
O1 B1 N2 102.63(13) . . ?
C26 B1 N2 96.40(12) . . ?
O3 B2 O2 116.20(14) . . ?
O3 B2 C13 113.91(15) . . ?
O2 B2 C13 115.14(14) . . ?
O3 B2 N1 110.40(13) . . ?
O2 B2 N1 102.46(13) . . ?
C13 B2 N1 95.88(12) . . ?
O1 C1 C2 107.25(13) . . ?
O1 C1 C6 109.30(13) . . ?
C2 C1 C6 110.73(14) . . ?
O1 C1 H1 109.8 . . ?
C2 C1 H1 109.8 . . ?
C6 C1 H1 109.8 . . ?
C3 C2 C1 113.67(15) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 109.91(16) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 110.22(15) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 112.11(15) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 112.18(14) . . ?
N1 C6 C1 109.36(13) . . ?
C5 C6 C1 112.92(14) . . ?
N1 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C1 C6 H6 107.4 . . ?
N1 C7 C8 113.87(15) . . ?
N1 C7 H7 123.1 . . ?
C8 C7 H7 123.1 . . ?
C9 C8 C13 123.73(17) . . ?
C9 C8 C7 126.19(16) . . ?
C13 C8 C7 110.08(15) . . ?
C10 C9 C8 117.88(17) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 119.80(17) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 121.31(18) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 120.56(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 116.73(16) . . ?
C12 C13 B2 133.96(16) . . ?
C8 C13 B2 109.31(15) . . ?
O2 C14 C15 106.71(13) . . ?
O2 C14 C19 110.71(14) . . ?
C15 C14 C19 110.43(14) . . ?
O2 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C19 C14 H14 109.7 . . ?
C16 C15 C14 113.70(15) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 109.39(16) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 110.53(17) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 112.28(15) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
N2 C19 C18 111.79(14) . . ?
N2 C19 C14 110.12(13) . . ?
C18 C19 C14 112.84(14) . . ?
N2 C19 H19 107.3 . . ?
C18 C19 H19 107.3 . . ?
C14 C19 H19 107.3 . . ?
N2 C20 C21 113.78(15) . . ?
N2 C20 H20 123.1 . . ?
C21 C20 H20 123.1 . . ?
C22 C21 C26 123.23(17) . . ?
C22 C21 C20 126.76(16) . . ?
C26 C21 C20 110.00(15) . . ?
C23 C22 C21 117.86(18) . . ?
C23 C22 H22 121.1 . . ?
C21 C22 H22 121.1 . . ?
C22 C23 C24 120.33(17) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 120.83(18) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 120.27(18) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 117.45(16) . . ?
C25 C26 B1 133.30(16) . . ?
C21 C26 B1 109.24(15) . . ?
Cl3 C30 Cl1 110.91(13) . . ?
Cl3 C30 Cl2 109.98(14) . . ?
Cl1 C30 Cl2 108.99(13) . . ?
Cl3 C30 H30 109.0 . . ?
Cl1 C30 H30 109.0 . . ?
Cl2 C30 H30 109.0 . . ?
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
N1 C7 1.284(2) . ?
N1 C6 1.475(2) . ?
N1 B2 1.682(2) . ?
N2 C20 1.285(2) . ?
N2 C19 1.476(2) . ?
N2 B1 1.673(2) . ?
O1 C1 1.4175(19) . ?
O1 B1 1.454(2) . ?
O2 C14 1.4197(19) . ?
O2 B2 1.456(2) . ?
O3 B2 1.426(2) . ?
O3 B1 1.430(2) . ?
B1 C26 1.625(2) . ?
B2 C13 1.634(3) . ?
C1 C2 1.528(2) . ?
C1 C6 1.539(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.527(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.524(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C7 C8 1.456(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 C13 1.407(2) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.529(2) . ?
C14 C19 1.541(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.531(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19 1.0000 . ?
C20 C21 1.457(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(2) . ?
C21 C26 1.402(2) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(3) . ?
C25 H25 0.9500 . ?
C30 Cl3 1.742(2) . ?
C30 Cl1 1.743(2) . ?
C30 Cl2 1.744(2) . ?
C30 H30 1.0000 . ?
