data_global
_journal_name_full 'Green Chemistry'
_journal_coden_Cambridge 1048
_audit_update_record
;
2007-08-03 # Formatted by publCIF
;
_publ_contact_author 'Dr Andrew Whiting'
_publ_contact_author_email ANDY.WHITING@DURHAM.AC.UK
_journal_volume ?
_journal_page_first ?
_journal_page_last ?
_journal_year ?
_database_code_depnum_ccdc_journal ?
_publ_section_title
;
Synthesis, evaluation and application of bifunctional
N,N-di-isopropylbenzylamine boronic acids catalysts for direct
amide condensation between carboxylic acids and amines
;
_publ_contact_author_name 'Dr Andrew Whiting'
loop_
_publ_author_name
K.Arnold
B.Davies
A.S.Batsanov
A.Whiting
#=============================================================
data_(6a)
_database_code_depnum_ccdc_archive 'CCDC 632237'
_database_code_CSD 632237
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N,N-Diisopropyl-3-fluorobenzylamine-2-boronic acid
;
_chemical_name_common
'N,N-Diisopropyl-3-fluorobenzylamine-2-boronic acid'
_chemical_melting_point 384
_chemical_formula_moiety 'C13 H21 B F N O2'
_chemical_formula_sum 'C13 H21 B F N O2'
_chemical_formula_weight 253.12
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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 13.748(2)
_cell_length_b 7.701(1)
_cell_length_c 13.781(2)
_cell_angle_alpha 90.00
_cell_angle_beta 110.97(1)
_cell_angle_gamma 90.00
_cell_volume 1362.4(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 9668
_cell_measurement_theta_min 2.99
_cell_measurement_theta_max 28.97
_exptl_crystal_description parallelepiped
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.4
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.2
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.234
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 544
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;The data collection nominally covered full sphere of reciprocal
space, by a combination of 4 runs of narrow-frame \w-scans (scan
width 0.3\% \w, 10s exposure), every run at a different \f angle.
Crystal to detector distance 4.40 cm.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number 0
_diffrn_reflns_number 15676
_diffrn_reflns_av_R_equivalents 0.0418
_diffrn_reflns_av_sigmaI/netI 0.0254
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 1.59
_diffrn_reflns_theta_max 28.97
_reflns_number_total 3616
_reflns_number_gt 3192
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART version 5.049 (Bruker, 1998)'
_computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)'
_computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)'
_computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.3439P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3616
_refine_ls_number_parameters 247
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0436
_refine_ls_R_factor_gt 0.0374
_refine_ls_wR_factor_ref 0.1070
_refine_ls_wR_factor_gt 0.1019
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_restrained_S_all 1.033
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
F F 0.81079(5) 0.31412(9) 0.51898(5) 0.02841(16) Uani 1 1 d . . .
N N 0.69617(6) 0.63667(10) 0.81339(6) 0.01613(16) Uani 1 1 d . . .
B B 0.65058(8) 0.43779(14) 0.59035(8) 0.0189(2) Uani 1 1 d . . .
O1 O 0.59332(5) 0.55515(9) 0.62006(5) 0.02116(16) Uani 1 1 d . . .
H01 H 0.6296(14) 0.600(2) 0.6885(15) 0.055(5) Uiso 1 1 d . . .
O2 O 0.61039(6) 0.35851(11) 0.49633(6) 0.02744(18) Uani 1 1 d . . .
H02 H 0.5441(14) 0.389(2) 0.4621(14) 0.049(5) Uiso 1 1 d . . .
C1 C 0.80205(7) 0.39633(12) 0.77483(7) 0.01691(18) Uani 1 1 d . . .
C2 C 0.76569(7) 0.38654(12) 0.66466(7) 0.01719(18) Uani 1 1 d . . .
C3 C 0.83762(8) 0.32127(13) 0.62388(7) 0.0207(2) Uani 1 1 d . . .
C4 C 0.93654(8) 0.26248(15) 0.68130(9) 0.0262(2) Uani 1 1 d . . .
H4 H 0.9809(11) 0.2115(19) 0.6450(11) 0.031(4) Uiso 1 1 d . . .
C5 C 0.96898(8) 0.27205(15) 0.78838(9) 0.0272(2) Uani 1 1 d . . .
H5 H 1.0396(13) 0.231(2) 0.8319(12) 0.038(4) Uiso 1 1 d . . .
C6 C 0.90243(8) 0.33999(13) 0.83429(8) 0.0217(2) Uani 1 1 d . . .
H6 H 0.9252(11) 0.3459(18) 0.9094(11) 0.026(3) Uiso 1 1 d . . .
C7 C 0.73473(7) 0.45559(12) 0.83498(7) 0.01801(19) Uani 1 1 d . . .
H71 H 0.6734(10) 0.3810(17) 0.8193(10) 0.021(3) Uiso 1 1 d . . .
H72 H 0.7760(10) 0.4395(17) 0.9098(10) 0.022(3) Uiso 1 1 d . . .
C8 C 0.62479(8) 0.68238(13) 0.87061(8) 0.0209(2) Uani 1 1 d . . .
H8 H 0.6262(10) 0.8092(18) 0.8751(10) 0.022(3) Uiso 1 1 d . . .
C9 C 0.51343(8) 0.62887(15) 0.80617(10) 0.0279(2) Uani 1 1 d . . .
H91 H 0.4891(12) 0.687(2) 0.7362(12) 0.037(4) Uiso 1 1 d . . .
H92 H 0.5081(12) 0.501(2) 0.7964(11) 0.035(4) Uiso 1 1 d . . .
H93 H 0.4663(12) 0.665(2) 0.8430(12) 0.039(4) Uiso 1 1 d . . .
C10 C 0.65453(10) 0.60695(17) 0.98019(9) 0.0314(3) Uani 1 1 d . . .
H101 H 0.6463(12) 0.479(2) 0.9788(12) 0.039(4) Uiso 1 1 d . . .
H102 H 0.7279(13) 0.631(2) 1.0245(12) 0.038(4) Uiso 1 1 d . . .
H103 H 0.6072(13) 0.661(2) 1.0138(12) 0.044(4) Uiso 1 1 d . . .
C11 C 0.78144(7) 0.76416(13) 0.82605(8) 0.0193(2) Uani 1 1 d . . .
H11 H 0.8234(10) 0.7123(17) 0.7869(10) 0.019(3) Uiso 1 1 d . . .
C12 C 0.73779(9) 0.93673(14) 0.77469(9) 0.0257(2) Uani 1 1 d . . .
H121 H 0.6848(12) 0.917(2) 0.7046(12) 0.034(4) Uiso 1 1 d . . .
H122 H 0.7084(11) 1.0027(19) 0.8176(11) 0.030(3) Uiso 1 1 d . . .
H123 H 0.7946(12) 1.005(2) 0.7660(12) 0.037(4) Uiso 1 1 d . . .
C13 C 0.85506(9) 0.79239(16) 0.93809(9) 0.0292(2) Uani 1 1 d . . .
H131 H 0.8187(12) 0.849(2) 0.9821(12) 0.034(4) Uiso 1 1 d . . .
H132 H 0.8861(12) 0.682(2) 0.9718(12) 0.039(4) Uiso 1 1 d . . .
H133 H 0.9113(13) 0.867(2) 0.9364(12) 0.041(4) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F 0.0317(3) 0.0355(4) 0.0190(3) -0.0062(2) 0.0103(3) 0.0009(3)
N 0.0157(3) 0.0148(4) 0.0173(3) -0.0009(3) 0.0052(3) 0.0006(3)
B 0.0194(5) 0.0182(5) 0.0167(4) 0.0006(4) 0.0033(4) 0.0003(4)
O1 0.0190(3) 0.0223(3) 0.0172(3) -0.0031(3) 0.0004(3) 0.0028(3)
O2 0.0245(4) 0.0306(4) 0.0199(3) -0.0075(3) -0.0010(3) 0.0063(3)
C1 0.0171(4) 0.0145(4) 0.0177(4) -0.0004(3) 0.0044(3) 0.0005(3)
C2 0.0177(4) 0.0148(4) 0.0172(4) -0.0013(3) 0.0040(3) -0.0007(3)
C3 0.0233(5) 0.0203(4) 0.0184(4) -0.0032(3) 0.0075(4) -0.0017(4)
C4 0.0212(5) 0.0289(5) 0.0299(5) -0.0046(4) 0.0110(4) 0.0021(4)
C5 0.0175(4) 0.0312(5) 0.0297(5) -0.0001(4) 0.0044(4) 0.0045(4)
C6 0.0190(4) 0.0235(5) 0.0195(4) 0.0000(4) 0.0031(4) 0.0022(4)
C7 0.0198(4) 0.0165(4) 0.0173(4) 0.0014(3) 0.0063(3) 0.0023(3)
C8 0.0215(4) 0.0200(4) 0.0228(4) -0.0026(4) 0.0100(4) 0.0016(4)
C9 0.0199(5) 0.0273(5) 0.0387(6) -0.0060(5) 0.0132(4) -0.0004(4)
C10 0.0395(6) 0.0358(6) 0.0248(5) 0.0018(4) 0.0186(5) 0.0065(5)
C11 0.0164(4) 0.0178(4) 0.0213(4) -0.0030(3) 0.0038(3) -0.0017(3)
C12 0.0263(5) 0.0184(5) 0.0310(5) 0.0015(4) 0.0087(4) -0.0020(4)
C13 0.0217(5) 0.0301(6) 0.0276(5) -0.0073(4) -0.0013(4) -0.0017(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
F C3 1.3591(11) . ?
N C7 1.4837(12) . ?
N C11 1.4907(12) . ?
N C8 1.5042(12) . ?
B O1 1.3547(13) . ?
B O2 1.3581(13) . ?
B C2 1.5965(14) . ?
O1 H01 0.960(19) . ?
O2 H02 0.895(18) . ?
C1 C6 1.3981(13) . ?
C1 C2 1.4204(12) . ?
C1 C7 1.5171(13) . ?
C2 C3 1.3943(14) . ?
C3 C4 1.3822(15) . ?
C4 C5 1.3824(16) . ?
C4 H4 0.998(14) . ?
C5 C6 1.3875(15) . ?
C5 H5 0.992(16) . ?
C6 H6 0.969(14) . ?
C7 H71 0.978(13) . ?
C7 H72 0.991(13) . ?
C8 C9 1.5261(15) . ?
C8 C10 1.5307(15) . ?
C8 H8 0.978(14) . ?
C9 H91 1.004(16) . ?
C9 H92 0.996(16) . ?
C9 H93 0.996(15) . ?
C10 H101 0.989(17) . ?
C10 H102 0.991(16) . ?
C10 H103 1.015(17) . ?
C11 C12 1.5242(14) . ?
C11 C13 1.5287(14) . ?
C11 H11 1.004(13) . ?
C12 H121 0.991(15) . ?
C12 H122 0.970(14) . ?
C12 H123 0.983(16) . ?
C13 H131 1.013(15) . ?
C13 H132 0.993(16) . ?
C13 H133 0.971(17) . ?
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 N C11 112.71(7) . . ?
C7 N C8 111.60(7) . . ?
C11 N C8 114.69(7) . . ?
O1 B O2 120.42(9) . . ?
O1 B C2 121.39(8) . . ?
O2 B C2 118.18(9) . . ?
B O1 H01 112.6(11) . . ?
B O2 H02 111.9(11) . . ?
C6 C1 C2 120.40(9) . . ?
C6 C1 C7 116.13(8) . . ?
C2 C1 C7 123.36(8) . . ?
C3 C2 C1 114.89(8) . . ?
C3 C2 B 120.91(8) . . ?
C1 C2 B 124.15(8) . . ?
F C3 C4 115.63(9) . . ?
F C3 C2 118.79(9) . . ?
C4 C3 C2 125.57(9) . . ?
C3 C4 C5 117.98(10) . . ?
C3 C4 H4 119.6(8) . . ?
C5 C4 H4 122.4(8) . . ?
C4 C5 C6 119.56(9) . . ?
C4 C5 H5 120.0(9) . . ?
C6 C5 H5 120.4(9) . . ?
C5 C6 C1 121.56(9) . . ?
C5 C6 H6 119.4(8) . . ?
C1 C6 H6 119.0(8) . . ?
N C7 C1 114.66(8) . . ?
N C7 H71 106.9(8) . . ?
C1 C7 H71 110.4(8) . . ?
N C7 H72 110.9(8) . . ?
C1 C7 H72 107.3(8) . . ?
H71 C7 H72 106.5(11) . . ?
N C8 C9 109.79(8) . . ?
N C8 C10 115.74(8) . . ?
C9 C8 C10 109.25(9) . . ?
N C8 H8 105.4(8) . . ?
C9 C8 H8 107.4(8) . . ?
C10 C8 H8 108.9(8) . . ?
C8 C9 H91 111.0(9) . . ?
C8 C9 H92 110.9(9) . . ?
H91 C9 H92 109.1(12) . . ?
C8 C9 H93 109.1(9) . . ?
H91 C9 H93 108.1(13) . . ?
H92 C9 H93 108.6(13) . . ?
C8 C10 H101 111.7(9) . . ?
C8 C10 H102 113.0(9) . . ?
H101 C10 H102 106.2(13) . . ?
C8 C10 H103 107.7(9) . . ?
H101 C10 H103 109.4(13) . . ?
H102 C10 H103 108.6(13) . . ?
N C11 C12 110.95(8) . . ?
N C11 C13 114.87(9) . . ?
C12 C11 C13 110.69(9) . . ?
N C11 H11 104.7(7) . . ?
C12 C11 H11 107.7(7) . . ?
C13 C11 H11 107.4(7) . . ?
C11 C12 H121 110.5(9) . . ?
C11 C12 H122 110.7(8) . . ?
H121 C12 H122 110.6(12) . . ?
C11 C12 H123 108.9(9) . . ?
H121 C12 H123 107.5(12) . . ?
H122 C12 H123 108.5(12) . . ?
C11 C13 H131 112.1(9) . . ?
C11 C13 H132 111.7(9) . . ?
H131 C13 H132 108.3(12) . . ?
C11 C13 H133 107.7(10) . . ?
H131 C13 H133 108.9(13) . . ?
H132 C13 H133 108.0(13) . . ?
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
C6 C1 C2 C3 -1.12(13) . . . . ?
C7 C1 C2 C3 -177.09(9) . . . . ?
C6 C1 C2 B 176.54(9) . . . . ?
C7 C1 C2 B 0.58(14) . . . . ?
O1 B C2 C3 -155.70(10) . . . . ?
O2 B C2 C3 25.22(14) . . . . ?
O1 B C2 C1 26.77(15) . . . . ?
O2 B C2 C1 -152.31(10) . . . . ?
C1 C2 C3 F -177.32(8) . . . . ?
B C2 C3 F 4.93(14) . . . . ?
C1 C2 C3 C4 2.24(15) . . . . ?
B C2 C3 C4 -175.51(10) . . . . ?
F C3 C4 C5 177.99(10) . . . . ?
C2 C3 C4 C5 -1.59(17) . . . . ?
C3 C4 C5 C6 -0.26(17) . . . . ?
C4 C5 C6 C1 1.26(17) . . . . ?
C2 C1 C6 C5 -0.52(15) . . . . ?
C7 C1 C6 C5 175.72(10) . . . . ?
C11 N C7 C1 -52.79(10) . . . . ?
C8 N C7 C1 176.46(8) . . . . ?
C6 C1 C7 N 121.99(9) . . . . ?
C2 C1 C7 N -61.89(12) . . . . ?
C7 N C8 C9 -86.74(10) . . . . ?
C11 N C8 C9 143.54(9) . . . . ?
C7 N C8 C10 37.50(12) . . . . ?
C11 N C8 C10 -92.23(11) . . . . ?
C7 N C11 C12 163.88(8) . . . . ?
C8 N C11 C12 -66.95(10) . . . . ?
C7 N C11 C13 -69.64(11) . . . . ?
C8 N C11 C13 59.53(11) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H01 N 0.960(19) 1.659(19) 2.6069(11) 168.5(17) .
O2 H02 O1 0.895(18) 1.872(19) 2.7646(11) 174.9(17) 3_666
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 28.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.352
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.039
#===================================END
data_(10)
_database_code_depnum_ccdc_archive 'CCDC 632238'
_database_code_CSD 632238
_audit_creation_method SHELXL-97
_chemical_name_systematic
; N,N-Diisopropyl-5-trifluoromethylbenzylamine-2-boronic
acid
;
_chemical_name_common
'N,N-Diisopropyl-5-trifluoromethylbenzylamine-2-boronic acid'
_chemical_melting_point 389
_chemical_formula_moiety 'C14 H21 B F3 N O2'
_chemical_formula_sum 'C14 H21 B F3 N O2'
_chemical_formula_weight 303.13
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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.4653(18)
_cell_length_b 7.7851(9)
_cell_length_c 13.2548(15)
_cell_angle_alpha 90.00
_cell_angle_beta 105.71(1)
_cell_angle_gamma 90.00
_cell_volume 1536.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 5776
_cell_measurement_theta_min 2.74
_cell_measurement_theta_max 28.99
_exptl_crystal_description parallelepip
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.65
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.311
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.109
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.1350
-1.00 0.00 0.00 0.1350
-1.00 1.00 1.00 0.0650
1.00 -1.00 -1.00 0.0650
1.00 1.00 -1.00 0.2300
-2.00 -1.00 3.00 0.2400
_exptl_special_details
;The data collection nominally covered over a hemisphere of reciprocal
space, by a combination of 3 runs of narrow-frame \w-scans (scan
width 0.3\% \w, 5s exposure), every run at a different \f angle.
Crystal to detector distance 4.41 cm.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Siemens 1K CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number 0
_diffrn_reflns_number 12199
_diffrn_reflns_av_R_equivalents 0.0398
_diffrn_reflns_av_sigmaI/netI 0.0320
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 1.37
_diffrn_reflns_theta_max 28.99
_reflns_number_total 4059
_reflns_number_gt 3248
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART version 5.049 (Bruker, 1998)'
_computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)'
_computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)'
_computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.4413P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4059
_refine_ls_number_parameters 274
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0563
_refine_ls_R_factor_gt 0.0420
_refine_ls_wR_factor_ref 0.1119
_refine_ls_wR_factor_gt 0.1045
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
F1 F -0.04871(6) 0.19887(15) 0.25827(8) 0.0519(3) Uani 1 1 d . . .
F2 F -0.03995(6) 0.36853(14) 0.13451(9) 0.0590(3) Uani 1 1 d . . .
F3 F -0.00168(6) 0.10517(14) 0.13111(9) 0.0558(3) Uani 1 1 d . . .
O1 O 0.42355(5) 0.54575(11) 0.38103(7) 0.02086(19) Uani 1 1 d . . .
H01 H 0.3940(13) 0.592(3) 0.3138(16) 0.051(5) Uiso 1 1 d . . .
O2 O 0.40227(6) 0.36640(12) 0.51644(7) 0.0239(2) Uani 1 1 d . . .
H02 H 0.4535(13) 0.400(2) 0.5481(15) 0.042(5) Uiso 1 1 d . . .
N N 0.33121(6) 0.62897(12) 0.19055(7) 0.0176(2) Uani 1 1 d . . .
B B 0.37216(8) 0.43470(17) 0.41867(10) 0.0185(3) Uani 1 1 d . . .
C1 C 0.24101(8) 0.39282(14) 0.24273(9) 0.0183(2) Uani 1 1 d . . .
C2 C 0.27388(7) 0.38147(14) 0.35321(9) 0.0182(2) Uani 1 1 d . . .
C3 C 0.21545(8) 0.32020(16) 0.40924(10) 0.0226(2) Uani 1 1 d . . .
H3 H 0.2368(10) 0.312(2) 0.4869(12) 0.024(4) Uiso 1 1 d . . .
C4 C 0.12719(8) 0.27287(17) 0.36044(11) 0.0261(3) Uani 1 1 d . . .
H4 H 0.0885(11) 0.233(2) 0.4002(13) 0.031(4) Uiso 1 1 d . . .
C5 C 0.09671(8) 0.28502(16) 0.25274(10) 0.0245(3) Uani 1 1 d . . .
C6 C 0.15302(8) 0.34364(15) 0.19437(10) 0.0222(2) Uani 1 1 d . . .
H6 H 0.1316(11) 0.355(2) 0.1182(13) 0.031(4) Uiso 1 1 d . . .
C7 C 0.29767(8) 0.45064(15) 0.17162(9) 0.0201(2) Uani 1 1 d . . .
H71 H 0.3515(10) 0.3769(19) 0.1829(11) 0.021(3) Uiso 1 1 d . . .
H72 H 0.2614(9) 0.4353(18) 0.0989(11) 0.018(3) Uiso 1 1 d . . .
C8 C 0.39251(9) 0.67397(16) 0.12391(10) 0.0232(3) Uani 1 1 d . . .
H8 H 0.3939(9) 0.7999(19) 0.1202(11) 0.019(3) Uiso 1 1 d . . .
C9 C 0.48805(9) 0.61623(19) 0.17775(12) 0.0310(3) Uani 1 1 d . . .
H91 H 0.5109(12) 0.676(2) 0.2481(15) 0.043(5) Uiso 1 1 d . . .
H92 H 0.5272(12) 0.648(2) 0.1316(14) 0.042(5) Uiso 1 1 d . . .
H93 H 0.4922(11) 0.491(2) 0.1858(13) 0.040(5) Uiso 1 1 d . . .
C10 C 0.36478(12) 0.6045(2) 0.01183(11) 0.0357(3) Uani 1 1 d . . .
H101 H 0.3712(12) 0.477(3) 0.0111(14) 0.043(5) Uiso 1 1 d . . .
H102 H 0.4046(11) 0.657(2) -0.0257(13) 0.037(4) Uiso 1 1 d . . .
H103 H 0.3032(13) 0.633(2) -0.0255(14) 0.045(5) Uiso 1 1 d . . .
C11 C 0.25743(8) 0.75506(15) 0.18702(10) 0.0208(2) Uani 1 1 d . . .
H11 H 0.2263(10) 0.7100(19) 0.2367(11) 0.021(3) Uiso 1 1 d . . .
C12 C 0.29520(9) 0.92955(17) 0.22834(11) 0.0257(3) Uani 1 1 d . . .
H121 H 0.3429(11) 0.917(2) 0.2925(13) 0.031(4) Uiso 1 1 d . . .
H122 H 0.3179(10) 0.995(2) 0.1756(12) 0.032(4) Uiso 1 1 d . . .
H123 H 0.2466(12) 0.995(2) 0.2414(14) 0.045(5) Uiso 1 1 d . . .
C13 C 0.18820(10) 0.7746(2) 0.08090(12) 0.0354(3) Uani 1 1 d . . .
H131 H 0.2150(12) 0.834(2) 0.0289(14) 0.043(5) Uiso 1 1 d . . .
H132 H 0.1615(14) 0.663(3) 0.0544(16) 0.056(5) Uiso 1 1 d . . .
H133 H 0.1401(14) 0.848(3) 0.0892(16) 0.055(5) Uiso 1 1 d . . .
C14 C 0.00183(9) 0.23892(19) 0.19500(12) 0.0338(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0209(4) 0.0701(7) 0.0635(6) 0.0027(5) 0.0096(4) -0.0121(4)
F2 0.0308(5) 0.0505(6) 0.0744(7) 0.0180(5) -0.0222(5) -0.0066(4)
F3 0.0350(5) 0.0556(6) 0.0703(7) -0.0278(5) 0.0030(5) -0.0181(5)
O1 0.0186(4) 0.0226(4) 0.0187(4) 0.0029(3) 0.0004(3) -0.0025(3)
O2 0.0211(4) 0.0283(5) 0.0191(4) 0.0039(3) 0.0001(3) -0.0040(4)
N 0.0193(5) 0.0162(5) 0.0171(4) 0.0006(4) 0.0047(4) 0.0002(4)
B 0.0183(6) 0.0171(6) 0.0193(6) -0.0012(5) 0.0035(5) 0.0010(5)
C1 0.0199(5) 0.0136(5) 0.0205(5) -0.0005(4) 0.0042(4) 0.0002(4)
C2 0.0181(5) 0.0143(5) 0.0208(5) 0.0001(4) 0.0027(4) 0.0008(4)
C3 0.0229(6) 0.0215(6) 0.0226(6) 0.0034(5) 0.0048(5) -0.0002(5)
C4 0.0217(6) 0.0250(6) 0.0322(7) 0.0052(5) 0.0083(5) -0.0026(5)
C5 0.0175(5) 0.0196(6) 0.0325(7) 0.0008(5) 0.0003(5) -0.0019(4)
C6 0.0218(6) 0.0188(6) 0.0225(6) -0.0006(5) 0.0001(5) -0.0007(4)
C7 0.0246(6) 0.0170(5) 0.0185(6) -0.0023(4) 0.0056(4) -0.0011(4)
C8 0.0301(6) 0.0198(6) 0.0224(6) 0.0024(5) 0.0114(5) -0.0011(5)
C9 0.0273(6) 0.0302(7) 0.0409(8) 0.0062(6) 0.0182(6) 0.0017(5)
C10 0.0516(9) 0.0364(8) 0.0237(7) -0.0015(6) 0.0181(7) -0.0065(7)
C11 0.0192(5) 0.0186(6) 0.0227(6) 0.0019(4) 0.0023(4) 0.0030(4)
C12 0.0296(6) 0.0189(6) 0.0279(7) -0.0012(5) 0.0067(5) 0.0020(5)
C13 0.0307(7) 0.0315(8) 0.0337(8) 0.0040(6) -0.0090(6) 0.0042(6)
C14 0.0220(6) 0.0325(7) 0.0419(8) 0.0017(6) 0.0001(6) -0.0052(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
F1 C14 1.3292(18) . ?
F2 C14 1.3408(18) . ?
F3 C14 1.3339(18) . ?
O1 B 1.3575(15) . ?
O1 H01 0.96(2) . ?
O2 B 1.3609(16) . ?
O2 H02 0.83(2) . ?
N C7 1.4795(15) . ?
N C11 1.4962(15) . ?
N C8 1.5017(15) . ?
B C2 1.5876(17) . ?
C1 C6 1.3917(16) . ?
C1 C2 1.4169(16) . ?
C1 C7 1.5187(16) . ?
C2 C3 1.3997(16) . ?
C3 C4 1.3925(17) . ?
C3 H3 0.995(15) . ?
C4 C5 1.3801(19) . ?
C4 H4 0.949(17) . ?
C5 C6 1.3892(18) . ?
C5 C14 1.5031(18) . ?
C6 H6 0.977(16) . ?
C7 H71 0.988(15) . ?
C7 H72 0.982(14) . ?
C8 C9 1.5242(19) . ?
C8 C10 1.5293(19) . ?
C8 H8 0.982(15) . ?
C9 H91 1.016(19) . ?
C9 H92 1.001(18) . ?
C9 H93 0.982(19) . ?
C10 H101 0.99(2) . ?
C10 H102 0.979(17) . ?
C10 H103 0.972(19) . ?
C11 C12 1.5210(17) . ?
C11 C13 1.5271(18) . ?
C11 H11 0.979(15) . ?
C12 H121 0.968(17) . ?
C12 H122 1.003(16) . ?
C12 H123 0.964(19) . ?
C13 H131 1.007(19) . ?
C13 H132 0.98(2) . ?
C13 H133 0.97(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
B O1 H01 113.8(12) . . ?
B O2 H02 113.1(13) . . ?
C7 N C11 112.39(9) . . ?
C7 N C8 111.55(9) . . ?
C11 N C8 115.22(9) . . ?
O1 B O2 121.02(11) . . ?
O1 B C2 122.31(11) . . ?
O2 B C2 116.65(10) . . ?
C6 C1 C2 119.43(11) . . ?
C6 C1 C7 116.89(10) . . ?
C2 C1 C7 123.64(10) . . ?
C3 C2 C1 117.84(10) . . ?
C3 C2 B 117.33(10) . . ?
C1 C2 B 124.82(10) . . ?
C4 C3 C2 122.43(12) . . ?
C4 C3 H3 118.3(9) . . ?
C2 C3 H3 119.3(9) . . ?
C5 C4 C3 118.66(12) . . ?
C5 C4 H4 120.4(10) . . ?
C3 C4 H4 120.9(10) . . ?
C4 C5 C6 120.56(11) . . ?
C4 C5 C14 121.55(12) . . ?
C6 C5 C14 117.88(12) . . ?
C5 C6 C1 121.07(11) . . ?
C5 C6 H6 121.0(9) . . ?
C1 C6 H6 117.9(9) . . ?
N C7 C1 114.05(9) . . ?
N C7 H71 106.1(9) . . ?
C1 C7 H71 109.8(8) . . ?
N C7 H72 111.2(8) . . ?
C1 C7 H72 107.5(8) . . ?
H71 C7 H72 108.1(11) . . ?
N C8 C9 110.01(10) . . ?
N C8 C10 115.67(11) . . ?
C9 C8 C10 109.39(12) . . ?
N C8 H8 106.8(8) . . ?
C9 C8 H8 106.6(8) . . ?
C10 C8 H8 108.0(8) . . ?
C8 C9 H91 110.3(10) . . ?
C8 C9 H92 108.1(10) . . ?
H91 C9 H92 109.4(15) . . ?
C8 C9 H93 111.7(10) . . ?
H91 C9 H93 111.0(14) . . ?
H92 C9 H93 106.2(14) . . ?
C8 C10 H101 111.0(10) . . ?
C8 C10 H102 107.2(10) . . ?
H101 C10 H102 109.4(14) . . ?
C8 C10 H103 113.1(11) . . ?
H101 C10 H103 107.8(15) . . ?
H102 C10 H103 108.2(15) . . ?
N C11 C12 111.07(10) . . ?
N C11 C13 115.63(11) . . ?
C12 C11 C13 110.37(11) . . ?
N C11 H11 104.7(9) . . ?
C12 C11 H11 106.8(9) . . ?
C13 C11 H11 107.7(9) . . ?
C11 C12 H121 110.5(10) . . ?
C11 C12 H122 112.1(9) . . ?
H121 C12 H122 109.8(13) . . ?
C11 C12 H123 107.3(11) . . ?
H121 C12 H123 110.0(14) . . ?
H122 C12 H123 106.9(14) . . ?
C11 C13 H131 111.1(10) . . ?
C11 C13 H132 111.3(12) . . ?
H131 C13 H132 111.7(16) . . ?
C11 C13 H133 108.9(12) . . ?
H131 C13 H133 106.2(16) . . ?
H132 C13 H133 107.4(17) . . ?
F1 C14 F3 106.71(12) . . ?
F1 C14 F2 106.45(12) . . ?
F3 C14 F2 106.12(13) . . ?
F1 C14 C5 113.24(12) . . ?
F3 C14 C5 112.08(12) . . ?
F2 C14 C5 111.76(11) . . ?
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
C6 C1 C2 C3 0.08(16) . . . . ?
C7 C1 C2 C3 -177.69(11) . . . . ?
C6 C1 C2 B -179.37(11) . . . . ?
C7 C1 C2 B 2.86(18) . . . . ?
O1 B C2 C3 -157.36(11) . . . . ?
O2 B C2 C3 21.12(16) . . . . ?
O1 B C2 C1 22.09(18) . . . . ?
O2 B C2 C1 -159.42(11) . . . . ?
C1 C2 C3 C4 -0.76(18) . . . . ?
B C2 C3 C4 178.73(11) . . . . ?
C2 C3 C4 C5 0.78(19) . . . . ?
C3 C4 C5 C6 -0.12(19) . . . . ?
C3 C4 C5 C14 -178.98(12) . . . . ?
C4 C5 C6 C1 -0.54(19) . . . . ?
C14 C5 C6 C1 178.36(12) . . . . ?
C2 C1 C6 C5 0.55(18) . . . . ?
C7 C1 C6 C5 178.48(11) . . . . ?
C11 N C7 C1 -53.29(13) . . . . ?
C8 N C7 C1 175.55(10) . . . . ?
C6 C1 C7 N 119.91(11) . . . . ?
C2 C1 C7 N -62.27(15) . . . . ?
C7 N C8 C9 -85.26(12) . . . . ?
C11 N C8 C9 145.04(11) . . . . ?
C7 N C8 C10 39.27(15) . . . . ?
C11 N C8 C10 -90.43(13) . . . . ?
C7 N C11 C12 168.36(10) . . . . ?
C8 N C11 C12 -62.35(13) . . . . ?
C7 N C11 C13 -64.88(14) . . . . ?
C8 N C11 C13 64.40(14) . . . . ?
C4 C5 C14 F1 4.47(19) . . . . ?
C6 C5 C14 F1 -174.42(12) . . . . ?
C4 C5 C14 F3 -116.33(15) . . . . ?
C6 C5 C14 F3 64.79(16) . . . . ?
C4 C5 C14 F2 124.69(15) . . . . ?
C6 C5 C14 F2 -54.20(17) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H01 N 0.96(2) 1.68(2) 2.6232(13) 166.8(19) .
O2 H02 O1 0.83(2) 1.93(2) 2.7547(13) 174.3(19) 3_666
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 28.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.372
_refine_diff_density_min -0.220
_refine_diff_density_rms 0.042
#======================================END