# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
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data_4a_15srv002
_database_code_depnum_ccdc_archive 'CCDC 1551614'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2015-01-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_chemical_name_common ?
_chemical_name_systematic
;
Bis-3,4,5-trifluorophenylborinic acid benzylamine complex
;
_chemical_formula_moiety 'C19 H14 B F6 N O'
_chemical_formula_sum 'C19 H14 B F6 N O'
_chemical_formula_weight 397.12
_chemical_melting_point 393(2)
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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
_cell_length_a 9.03430(10)
_cell_length_b 10.2063(2)
_cell_length_c 11.0348(2)
_cell_angle_alpha 66.3381(18)
_cell_angle_beta 70.1856(17)
_cell_angle_gamma 78.1262(19)
_cell_volume 873.89(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9905
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 31.50
_cell_measurement_theta_min 2.19
_exptl_absorpt_coefficient_mu 0.136
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9474
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.9474.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier .
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.509
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 404
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.44
_exptl_crystal_size_min 0.2
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0316
_diffrn_reflns_av_unetI/netI 0.0306
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 18051
_diffrn_reflns_theta_full 28.99
_diffrn_reflns_theta_max 28.99
_diffrn_reflns_theta_min 2.10
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Bruker D8 Venture'
_diffrn_measurement_device_type D8Venture
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'iMuS microsource'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number 0
_reflns_number_gt 3848
_reflns_number_total 4649
_reflns_threshold_expression >2sigma(I)
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.418
_refine_diff_density_min -0.278
_refine_diff_density_rms 0.053
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 309
_refine_ls_number_reflns 4649
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0553
_refine_ls_R_factor_gt 0.0426
_refine_ls_restrained_S_all 1.042
_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/[\s^2^(Fo^2^)+(0.0450P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1000
_refine_ls_wR_factor_ref 0.1073
_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. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_refinement_flags_posn
F1 F -0.20075(12) 0.66672(10) 0.16511(11) 0.0412(3) Uani 1 d . . .
F2 F 0.04691(13) 0.77102(9) -0.05566(9) 0.0335(2) Uani 1 d . . .
F3 F 0.32604(12) 0.61085(11) -0.08381(9) 0.0396(3) Uani 1 d . . .
F4 F 0.63163(11) 0.26659(10) 0.38904(10) 0.0334(2) Uani 1 d . . .
F5 F 0.77197(9) 0.03468(11) 0.32070(9) 0.0330(2) Uani 1 d . . .
F6 F 0.60311(10) -0.12271(10) 0.27953(10) 0.0308(2) Uani 1 d . . .
O1 O 0.05580(11) 0.10150(9) 0.31688(9) 0.01477(19) Uani 1 d . . .
N1 N -0.00144(13) 0.18774(11) 0.50154(11) 0.0135(2) Uani 1 d . . .
C1 C 0.01192(16) 0.27091(14) 0.58187(14) 0.0184(3) Uani 1 d . . .
C2 C -0.13048(17) 0.25231(15) 0.70628(14) 0.0214(3) Uani 1 d . . .
C3 C -0.1303(2) 0.13788(17) 0.82935(15) 0.0285(3) Uani 1 d . . .
C4 C -0.2675(3) 0.1112(2) 0.93912(18) 0.0418(5) Uani 1 d . . .
C5 C -0.4036(2) 0.1987(2) 0.9268(2) 0.0473(5) Uani 1 d . . .
C6 C -0.4049(2) 0.3141(2) 0.8063(2) 0.0443(5) Uani 1 d . . .
C7 C -0.26766(19) 0.34075(18) 0.69556(18) 0.0313(3) Uani 1 d . . .
C8 C 0.09581(15) 0.36735(13) 0.24121(12) 0.0143(2) Uani 1 d . . .
C9 C -0.04806(16) 0.45144(14) 0.25229(14) 0.0195(3) Uani 1 d . . .
C10 C -0.06249(17) 0.58543(14) 0.15298(15) 0.0227(3) Uani 1 d . . .
C11 C 0.06228(19) 0.63966(14) 0.04019(14) 0.0227(3) Uani 1 d . . .
C12 C 0.20382(18) 0.55781(15) 0.02747(13) 0.0229(3) Uani 1 d . . .
C13 C 0.22200(16) 0.42413(14) 0.12590(13) 0.0192(3) Uani 1 d . . .
C14 C 0.29679(14) 0.15348(13) 0.35124(12) 0.0139(2) Uani 1 d . . .
C15 C 0.38706(16) 0.23236(14) 0.37516(13) 0.0180(3) Uani 1 d . . .
C16 C 0.54424(16) 0.19097(15) 0.36580(14) 0.0220(3) Uani 1 d . . .
C17 C 0.61746(15) 0.07319(16) 0.33190(13) 0.0220(3) Uani 1 d . . .
C18 C 0.52957(15) -0.00580(15) 0.31023(13) 0.0202(3) Uani 1 d . . .
C19 C 0.37194(15) 0.03288(14) 0.31846(13) 0.0161(2) Uani 1 d . . .
B1 B 0.11586(16) 0.20366(14) 0.34713(14) 0.0124(2) Uani 1 d . . .
H1 H 0.016(2) 0.140(2) 0.257(2) 0.035(5) Uiso 1 d . . .
H1A H -0.102(2) 0.2086(18) 0.4936(17) 0.020(4) Uiso 1 d . . .
H1B H -0.001(2) 0.0922(19) 0.5553(18) 0.023(4) Uiso 1 d . . .
H1C H 0.0227(19) 0.3710(18) 0.5185(17) 0.021(4) Uiso 1 d . . .
H1D H 0.110(2) 0.2338(18) 0.6113(17) 0.022(4) Uiso 1 d . . .
H3 H -0.035(2) 0.077(2) 0.8367(19) 0.033(5) Uiso 1 d . . .
H4 H -0.267(3) 0.026(3) 1.025(3) 0.062(7) Uiso 1 d . . .
H5 H -0.498(3) 0.182(3) 1.000(3) 0.061(7) Uiso 1 d . . .
H6 H -0.495(3) 0.377(3) 0.793(2) 0.053(6) Uiso 1 d . . .
H7 H -0.266(2) 0.416(2) 0.610(2) 0.035(5) Uiso 1 d . . .
H9 H -0.140(2) 0.4197(19) 0.3261(19) 0.027(4) Uiso 1 d . . .
H13 H 0.322(2) 0.3737(19) 0.1124(18) 0.026(4) Uiso 1 d . . .
H15 H 0.3441(18) 0.3166(17) 0.3971(16) 0.015(4) Uiso 1 d . . .
H19 H 0.3159(19) -0.0218(18) 0.2975(17) 0.022(4) Uiso 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 0.0348(5) 0.0252(5) 0.0518(6) -0.0043(4) -0.0192(5) 0.0140(4)
F2 0.0606(6) 0.0136(4) 0.0266(5) 0.0052(3) -0.0267(4) -0.0054(4)
F3 0.0461(6) 0.0343(5) 0.0171(4) 0.0074(4) 0.0032(4) -0.0143(4)
F4 0.0291(5) 0.0381(5) 0.0356(5) -0.0026(4) -0.0153(4) -0.0198(4)
F5 0.0109(4) 0.0438(6) 0.0293(5) 0.0026(4) -0.0057(3) -0.0041(4)
F6 0.0213(4) 0.0318(5) 0.0336(5) -0.0145(4) -0.0041(4) 0.0092(4)
O1 0.0169(4) 0.0129(4) 0.0153(4) -0.0026(3) -0.0078(3) -0.0026(3)
N1 0.0144(5) 0.0110(5) 0.0137(5) -0.0033(4) -0.0026(4) -0.0027(4)
C1 0.0212(6) 0.0157(6) 0.0187(6) -0.0081(5) -0.0015(5) -0.0055(5)
C2 0.0246(7) 0.0208(6) 0.0210(6) -0.0128(5) 0.0004(5) -0.0074(5)
C3 0.0397(9) 0.0278(8) 0.0195(7) -0.0126(6) -0.0014(6) -0.0093(7)
C4 0.0597(12) 0.0433(10) 0.0204(8) -0.0162(7) 0.0080(8) -0.0235(9)
C5 0.0436(10) 0.0628(13) 0.0379(10) -0.0343(10) 0.0184(8) -0.0271(10)
C6 0.0264(8) 0.0573(12) 0.0567(12) -0.0402(10) 0.0026(8) -0.0029(8)
C7 0.0294(8) 0.0303(8) 0.0355(9) -0.0197(7) -0.0015(7) -0.0020(6)
C8 0.0178(6) 0.0116(5) 0.0138(5) -0.0028(4) -0.0057(5) -0.0036(4)
C9 0.0185(6) 0.0156(6) 0.0212(6) -0.0022(5) -0.0064(5) -0.0026(5)
C10 0.0261(7) 0.0147(6) 0.0292(7) -0.0056(5) -0.0159(6) 0.0035(5)
C11 0.0420(8) 0.0104(6) 0.0183(6) 0.0014(5) -0.0185(6) -0.0046(5)
C12 0.0324(7) 0.0201(6) 0.0119(6) 0.0009(5) -0.0044(5) -0.0103(6)
C13 0.0221(6) 0.0167(6) 0.0149(6) -0.0023(5) -0.0038(5) -0.0031(5)
C14 0.0134(5) 0.0147(6) 0.0102(5) -0.0001(4) -0.0030(4) -0.0036(4)
C15 0.0199(6) 0.0163(6) 0.0159(6) -0.0009(5) -0.0056(5) -0.0070(5)
C16 0.0213(6) 0.0258(7) 0.0158(6) 0.0034(5) -0.0074(5) -0.0144(5)
C17 0.0107(5) 0.0297(7) 0.0148(6) 0.0035(5) -0.0030(5) -0.0041(5)
C18 0.0154(6) 0.0215(6) 0.0155(6) -0.0025(5) -0.0011(5) 0.0015(5)
C19 0.0147(6) 0.0173(6) 0.0132(5) -0.0026(5) -0.0030(4) -0.0022(5)
B1 0.0124(6) 0.0111(6) 0.0119(6) -0.0020(5) -0.0030(5) -0.0023(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 C10 1.3475(17) . ?
F2 C11 1.3491(14) . ?
F3 C12 1.3465(16) . ?
F4 C16 1.3533(15) . ?
F5 C17 1.3470(15) . ?
F6 C18 1.3511(16) . ?
O1 B1 1.4588(16) . ?
O1 H1 0.78(2) . ?
N1 C1 1.4965(16) . ?
N1 B1 1.6362(17) . ?
N1 H1A 0.912(17) . ?
N1 H1B 0.915(18) . ?
C1 C2 1.5066(18) . ?
C1 H1C 0.982(17) . ?
C1 H1D 0.995(17) . ?
C2 C3 1.391(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.96(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.99(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.94(2) . ?
C6 C7 1.396(2) . ?
C6 H6 0.94(2) . ?
C7 H7 0.95(2) . ?
C8 C9 1.3993(18) . ?
C8 C13 1.3968(18) . ?
C8 B1 1.6253(17) . ?
C9 C10 1.3815(18) . ?
C9 H9 0.948(18) . ?
C10 C11 1.371(2) . ?
C11 C12 1.373(2) . ?
C12 C13 1.3811(18) . ?
C13 H13 0.942(18) . ?
C14 C15 1.4034(17) . ?
C14 C19 1.3978(18) . ?
C14 B1 1.6196(18) . ?
C15 C16 1.3764(19) . ?
C15 H15 0.957(16) . ?
C16 C17 1.374(2) . ?
C17 C18 1.373(2) . ?
C18 C19 1.3791(18) . ?
C19 H19 0.959(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
B1 O1 H1 111.9(15) . . ?
C1 N1 B1 122.88(10) . . ?
C1 N1 H1A 106.6(10) . . ?
C1 N1 H1B 108.8(11) . . ?
B1 N1 H1A 106.3(10) . . ?
B1 N1 H1B 107.9(11) . . ?
H1A N1 H1B 102.6(15) . . ?
N1 C1 C2 109.18(10) . . ?
N1 C1 H1C 106.9(10) . . ?
N1 C1 H1D 108.6(10) . . ?
C2 C1 H1C 113.4(10) . . ?
C2 C1 H1D 110.2(10) . . ?
H1C C1 H1D 108.5(13) . . ?
C3 C2 C1 120.21(13) . . ?
C7 C2 C1 120.26(13) . . ?
C7 C2 C3 119.26(14) . . ?
C2 C3 H3 119.2(11) . . ?
C4 C3 C2 120.17(17) . . ?
C4 C3 H3 120.6(11) . . ?
C3 C4 H4 119.1(15) . . ?
C5 C4 C3 120.07(18) . . ?
C5 C4 H4 120.8(15) . . ?
C4 C5 C6 120.43(16) . . ?
C4 C5 H5 121.0(15) . . ?
C6 C5 H5 118.6(15) . . ?
C5 C6 C7 119.69(19) . . ?
C5 C6 H6 123.4(15) . . ?
C7 C6 H6 116.9(15) . . ?
C2 C7 C6 120.36(18) . . ?
C2 C7 H7 118.1(12) . . ?
C6 C7 H7 121.5(12) . . ?
C9 C8 B1 122.87(11) . . ?
C13 C8 C9 117.27(11) . . ?
C13 C8 B1 119.58(11) . . ?
C8 C9 H9 122.5(11) . . ?
C10 C9 C8 120.72(13) . . ?
C10 C9 H9 116.8(11) . . ?
F1 C10 C9 120.46(13) . . ?
F1 C10 C11 118.16(12) . . ?
C11 C10 C9 121.38(13) . . ?
F2 C11 C10 120.80(13) . . ?
F2 C11 C12 120.68(13) . . ?
C10 C11 C12 118.52(12) . . ?
F3 C12 C11 118.46(12) . . ?
F3 C12 C13 120.22(13) . . ?
C11 C12 C13 121.32(13) . . ?
C8 C13 H13 121.7(11) . . ?
C12 C13 C8 120.80(13) . . ?
C12 C13 H13 117.5(11) . . ?
C15 C14 B1 122.96(11) . . ?
C19 C14 C15 117.74(11) . . ?
C19 C14 B1 119.08(11) . . ?
C14 C15 H15 122.5(9) . . ?
C16 C15 C14 120.33(13) . . ?
C16 C15 H15 117.1(9) . . ?
F4 C16 C15 120.51(14) . . ?
F4 C16 C17 118.03(12) . . ?
C17 C16 C15 121.46(13) . . ?
F5 C17 C16 121.14(13) . . ?
F5 C17 C18 120.24(13) . . ?
C18 C17 C16 118.61(12) . . ?
F6 C18 C17 117.68(12) . . ?
F6 C18 C19 120.93(13) . . ?
C17 C18 C19 121.39(13) . . ?
C14 C19 H19 120.5(10) . . ?
C18 C19 C14 120.44(12) . . ?
C18 C19 H19 119.0(10) . . ?
O1 B1 N1 101.20(9) . . ?
O1 B1 C8 112.32(10) . . ?
O1 B1 C14 109.92(10) . . ?
C8 B1 N1 109.68(10) . . ?
C14 B1 N1 110.77(10) . . ?
C14 B1 C8 112.41(10) . . ?
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 H1 F2 0.78(2) 2.26(2) 3.0280(12) 166.3(19) 2_565
N1 H1B O1 0.915(18) 1.959(18) 2.8552(14) 165.8(15) 2_556
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
C1 N1 B1 O1 179.38(10) . . . . ?
C3 C2 C1 N1 88.08(15) . . . . ?
C7 C2 C1 N1 -85.87(15) . . . . ?
C8 B1 N1 C1 -61.81(14) . . . . ?
C8 B1 C14 C15 52.70(15) . . . . ?
C8 B1 C14 C19 -121.84(12) . . . . ?
C9 C8 B1 O1 77.93(15) . . . . ?
C9 C8 B1 N1 -33.78(16) . . . . ?
C13 C8 B1 O1 -95.80(13) . . . . ?
C13 C8 B1 N1 152.50(11) . . . . ?
C14 B1 N1 C1 62.85(14) . . . . ?
C14 B1 C8 C9 -157.48(12) . . . . ?
C14 B1 C8 C13 28.80(16) . . . . ?
C15 C14 B1 O1 178.60(11) . . . . ?
C15 C14 B1 N1 -70.39(14) . . . . ?
C19 C14 B1 O1 4.07(15) . . . . ?
C19 C14 B1 N1 115.07(12) . . . . ?
B1 N1 C1 C2 169.50(11) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
TITL 15srv002 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 9.0343 10.2063 11.0348 66.3381 70.1856 78.1262
ZERR 2 0.0001 0.0002 0.0002 0.0018 0.0017 0.0019
LATT 1
SFAC C H B N O F
UNIT 38 28 2 2 2 12
EQIV $1 -X,1-Y,-Z
EQIV $2 -X,-Y,1-Z
L.S. 9
PLAN 5
TEMP -153.15
HTAB O1 F2_$1
HTAB N1 O1_$2
CONF C1 N1 B1 O1
CONF C8 B1 N1 C1
CONF C14 B1 N1 C1
CONF B1 N1 C1 C2
CONF C3 C2 C1 N1
CONF C7 C2 C1 N1
CONF C9 C8 B1 O1
CONF C9 C8 B1 N1
CONF C14 B1 C8 C9
CONF C13 C8 B1 O1
CONF C13 C8 B1 N1
CONF C14 B1 C8 C13
CONF C15 C14 B1 O1
CONF C15 C14 B1 N1
CONF C8 B1 C14 C15
CONF C19 C14 B1 O1
CONF C19 C14 B1 N1
CONF C8 B1 C14 C19
BOND $h
fmap 2
acta
OMIT -2 58
REM
REM
REM
WGHT 0.045000 0.450000
FVAR 0.25869
F1 6 -0.200750 0.666721 0.165111 11.00000 0.03481 0.02522 =
0.05178 -0.00430 -0.01916 0.01397
F2 6 0.046907 0.771020 -0.055661 11.00000 0.06057 0.01363 =
0.02656 0.00524 -0.02672 -0.00538
F3 6 0.326039 0.610845 -0.083808 11.00000 0.04607 0.03431 =
0.01706 0.00744 0.00315 -0.01430
F4 6 0.631627 0.266587 0.389038 11.00000 0.02913 0.03806 =
0.03560 -0.00257 -0.01527 -0.01983
F5 6 0.771967 0.034678 0.320700 11.00000 0.01086 0.04378 =
0.02934 0.00255 -0.00565 -0.00408
F6 6 0.603115 -0.122708 0.279535 11.00000 0.02127 0.03178 =
0.03363 -0.01452 -0.00407 0.00919
O1 5 0.055804 0.101495 0.316881 11.00000 0.01694 0.01295 =
0.01526 -0.00264 -0.00778 -0.00258
N1 4 -0.001441 0.187736 0.501539 11.00000 0.01443 0.01102 =
0.01368 -0.00334 -0.00264 -0.00273
C1 1 0.011924 0.270912 0.581865 11.00000 0.02119 0.01568 =
0.01871 -0.00814 -0.00155 -0.00550
C2 1 -0.130481 0.252309 0.706276 11.00000 0.02463 0.02082 =
0.02101 -0.01285 0.00035 -0.00735
C3 1 -0.130292 0.137876 0.829353 11.00000 0.03971 0.02782 =
0.01946 -0.01255 -0.00137 -0.00931
C4 1 -0.267509 0.111193 0.939119 11.00000 0.05970 0.04332 =
0.02037 -0.01618 0.00804 -0.02348
C5 1 -0.403608 0.198678 0.926756 11.00000 0.04355 0.06284 =
0.03793 -0.03429 0.01835 -0.02711
C6 1 -0.404893 0.314057 0.806321 11.00000 0.02641 0.05726 =
0.05672 -0.04021 0.00262 -0.00288
C7 1 -0.267659 0.340750 0.695563 11.00000 0.02941 0.03027 =
0.03547 -0.01970 -0.00153 -0.00204
C8 1 0.095808 0.367350 0.241210 11.00000 0.01777 0.01163 =
0.01383 -0.00284 -0.00565 -0.00364
C9 1 -0.048055 0.451436 0.252286 11.00000 0.01845 0.01560 =
0.02118 -0.00222 -0.00637 -0.00261
C10 1 -0.062492 0.585429 0.152983 11.00000 0.02612 0.01474 =
0.02916 -0.00564 -0.01589 0.00346
C11 1 0.062276 0.639658 0.040186 11.00000 0.04196 0.01042 =
0.01831 0.00139 -0.01846 -0.00457
C12 1 0.203823 0.557815 0.027466 11.00000 0.03241 0.02011 =
0.01189 0.00092 -0.00437 -0.01035
C13 1 0.221998 0.424133 0.125901 11.00000 0.02207 0.01669 =
0.01494 -0.00230 -0.00377 -0.00313
C14 1 0.296785 0.153485 0.351243 11.00000 0.01338 0.01466 =
0.01015 -0.00012 -0.00297 -0.00363
C15 1 0.387059 0.232362 0.375160 11.00000 0.01993 0.01634 =
0.01592 -0.00089 -0.00557 -0.00696
C16 1 0.544242 0.190968 0.365804 11.00000 0.02128 0.02579 =
0.01582 0.00341 -0.00738 -0.01435
C17 1 0.617463 0.073188 0.331904 11.00000 0.01069 0.02967 =
0.01479 0.00352 -0.00297 -0.00415
C18 1 0.529571 -0.005802 0.310228 11.00000 0.01537 0.02151 =
0.01546 -0.00249 -0.00114 0.00151
C19 1 0.371942 0.032885 0.318464 11.00000 0.01469 0.01727 =
0.01319 -0.00263 -0.00297 -0.00216
B1 3 0.115859 0.203664 0.347128 11.00000 0.01239 0.01106 =
0.01189 -0.00201 -0.00300 -0.00229
H1 2 0.015816 0.139834 0.257342 11.00000 0.03531
H1A 2 -0.101597 0.208622 0.493559 11.00000 0.01993
H1B 2 -0.000645 0.092248 0.555266 11.00000 0.02318
H1C 2 0.022668 0.371011 0.518460 11.00000 0.02088
H1D 2 0.109814 0.233837 0.611319 11.00000 0.02162
H3 2 -0.035458 0.077187 0.836745 11.00000 0.03277
H4 2 -0.266629 0.026296 1.024818 11.00000 0.06221
H5 2 -0.497506 0.181549 0.999984 11.00000 0.06079
H6 2 -0.494920 0.376754 0.793233 11.00000 0.05294
H7 2 -0.266454 0.416286 0.610204 11.00000 0.03484
H9 2 -0.139958 0.419658 0.326063 11.00000 0.02747
H13 2 0.322418 0.373705 0.112434 11.00000 0.02629
H15 2 0.344131 0.316632 0.397139 11.00000 0.01506
H19 2 0.315888 -0.021813 0.297530 11.00000 0.02157
HKLF 4
REM 15srv002 in P-1 #2
REM R1 = 0.0426 for 3848 Fo > 4sig(Fo) and 0.0553 for all 4649 data
REM 309 parameters refined using 0 restraints
END
WGHT 0.0455 0.4544
REM Highest difference peak 0.418, deepest hole -0.278, 1-sigma level 0.053
Q1 1 0.2080 0.1847 0.3515 11.00000 0.05 0.42
Q2 1 0.5643 0.0414 0.3306 11.00000 0.05 0.33
Q3 1 0.1050 0.2923 0.2989 11.00000 0.05 0.32
Q4 1 0.1208 0.5821 0.0258 11.00000 0.05 0.31
Q5 1 0.5730 0.0556 0.2910 11.00000 0.05 0.31
;
#===END
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, DCM'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_5c_15srv050
_database_code_depnum_ccdc_archive 'CCDC 1551618'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2015-02-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic
;
Bis-(phenyl)borinic acid benzylaminobenzoate
;
_chemical_formula_moiety 'C H2 Cl2, C26 H24 B N O2'
_chemical_formula_sum 'C27 H26 B Cl2 N O2'
_chemical_formula_weight 478.20
_chemical_melting_point 380.7(5)
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'
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'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'
_cell_length_a 14.1158(3)
_cell_length_b 8.9604(2)
_cell_length_c 18.8756(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.0788(17)
_cell_angle_gamma 90.00
_cell_volume 2387.44(9)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9957
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 30.16
_cell_measurement_theta_min 2.52
_exptl_absorpt_coefficient_mu 0.297
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9141
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1203 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.330
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1000
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.1
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0689
_diffrn_reflns_av_unetI/netI 0.0656
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 35929
_diffrn_reflns_theta_full 29.00
_diffrn_reflns_theta_max 29.00
_diffrn_reflns_theta_min 2.52
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'Bruker D8 Venture'
_diffrn_measurement_device_type D8Venture
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'ImuS microsource'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number 0
_reflns_number_gt 4421
_reflns_number_total 6345
_reflns_threshold_expression >2sigma(I)
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.351
_refine_diff_density_min -0.387
_refine_diff_density_rms 0.061
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 402
_refine_ls_number_reflns 6345
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0883
_refine_ls_R_factor_gt 0.0488
_refine_ls_restrained_S_all 1.015
_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/[\s^2^(Fo^2^)+(0.0400P)^2^+1.3200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0972
_refine_ls_wR_factor_ref 0.1105
_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. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_refinement_flags_posn
Cl1 Cl 0.66909(4) 0.30124(7) 0.24053(3) 0.03273(14) Uani 1 d . . .
Cl2 Cl 0.72713(4) 0.51359(6) 0.13138(3) 0.03576(15) Uani 1 d . . .
C1S C 0.63097(15) 0.4344(3) 0.17770(13) 0.0300(5) Uani 1 d . . .
H1SA H 0.5903(16) 0.377(3) 0.1450(12) 0.033(6) Uiso 1 d . . .
H1SB H 0.6013(17) 0.514(3) 0.2022(13) 0.042(7) Uiso 1 d . . .
O1 O 0.32007(8) 0.67943(13) 0.10343(6) 0.0125(3) Uani 1 d . . .
O2 O 0.24982(8) 0.84930(13) 0.17254(6) 0.0156(3) Uani 1 d . . .
N1 N 0.24625(10) 0.54138(18) 0.20547(8) 0.0127(3) Uani 1 d . . .
C1 C 0.16802(12) 0.4575(2) 0.16815(10) 0.0162(4) Uani 1 d . . .
C2 C 0.11225(12) 0.5544(2) 0.11841(9) 0.0153(4) Uani 1 d . . .
C3 C 0.13372(13) 0.5599(2) 0.04652(10) 0.0205(4) Uani 1 d . . .
C4 C 0.08373(14) 0.6521(3) 0.00160(11) 0.0274(5) Uani 1 d . . .
C5 C 0.01213(14) 0.7412(3) 0.02764(11) 0.0291(5) Uani 1 d . . .
C6 C -0.01075(14) 0.7358(2) 0.09855(11) 0.0262(5) Uani 1 d . . .
C7 C 0.03867(13) 0.6419(2) 0.14360(10) 0.0196(4) Uani 1 d . . .
C8 C 0.27920(11) 0.80850(19) 0.11436(9) 0.0119(3) Uani 1 d . . .
C9 C 0.26956(11) 0.90224(19) 0.04982(9) 0.0126(3) Uani 1 d . . .
C10 C 0.29690(13) 0.8492(2) -0.01619(10) 0.0196(4) Uani 1 d . . .
C11 C 0.28767(15) 0.9387(2) -0.07553(11) 0.0263(5) Uani 1 d . . .
C12 C 0.25238(14) 1.0815(2) -0.06926(11) 0.0241(4) Uani 1 d . . .
C13 C 0.22500(14) 1.1354(2) -0.00385(11) 0.0221(4) Uani 1 d . . .
C14 C 0.23299(13) 1.0461(2) 0.05569(10) 0.0174(4) Uani 1 d . . .
C15 C 0.38199(11) 0.42073(19) 0.12910(9) 0.0120(3) Uani 1 d . . .
C16 C 0.39709(12) 0.2950(2) 0.17180(10) 0.0156(4) Uani 1 d . . .
C17 C 0.43663(13) 0.1647(2) 0.14588(10) 0.0187(4) Uani 1 d . . .
C18 C 0.46383(13) 0.1566(2) 0.07560(11) 0.0213(4) Uani 1 d . . .
C19 C 0.45023(14) 0.2785(2) 0.03204(11) 0.0225(4) Uani 1 d . . .
C20 C 0.40935(13) 0.4083(2) 0.05829(9) 0.0168(4) Uani 1 d . . .
C21 C 0.42107(11) 0.64568(19) 0.21580(9) 0.0126(3) Uani 1 d . . .
C22 C 0.43871(13) 0.5906(2) 0.28402(9) 0.0157(4) Uani 1 d . . .
C23 C 0.51265(13) 0.6446(2) 0.32557(10) 0.0208(4) Uani 1 d . . .
C24 C 0.57161(13) 0.7548(2) 0.29995(10) 0.0227(4) Uani 1 d . . .
C25 C 0.55618(13) 0.8120(2) 0.23256(10) 0.0198(4) Uani 1 d . . .
C26 C 0.48228(12) 0.7576(2) 0.19156(10) 0.0153(4) Uani 1 d . . .
B1 B 0.34338(13) 0.5738(2) 0.16289(10) 0.0116(4) Uani 1 d . . .
H1A H 0.2241(14) 0.630(2) 0.2178(10) 0.017(5) Uiso 1 d . . .
H1B H 0.2586(15) 0.490(2) 0.2446(12) 0.027(6) Uiso 1 d . . .
H1C H 0.1278(13) 0.417(2) 0.2051(10) 0.012(5) Uiso 1 d . . .
H1D H 0.1975(13) 0.376(2) 0.1425(10) 0.015(5) Uiso 1 d . . .
H3 H 0.1845(15) 0.500(2) 0.0285(11) 0.027(6) Uiso 1 d . . .
H4 H 0.0999(14) 0.654(2) -0.0473(12) 0.026(6) Uiso 1 d . . .
H5 H -0.0212(15) 0.804(3) -0.0033(12) 0.030(6) Uiso 1 d . . .
H6 H -0.0604(17) 0.795(3) 0.1148(12) 0.040(7) Uiso 1 d . . .
H7 H 0.0216(14) 0.638(2) 0.1921(11) 0.022(5) Uiso 1 d . . .
H10 H 0.3204(13) 0.753(2) -0.0195(10) 0.014(5) Uiso 1 d . . .
H11 H 0.3034(16) 0.901(3) -0.1212(13) 0.039(7) Uiso 1 d . . .
H12 H 0.2484(15) 1.143(3) -0.1110(12) 0.034(6) Uiso 1 d . . .
H13 H 0.2016(14) 1.238(3) -0.0002(11) 0.025(6) Uiso 1 d . . .
H14 H 0.2127(14) 1.082(2) 0.1003(11) 0.022(5) Uiso 1 d . . .
H16 H 0.3808(14) 0.299(2) 0.2208(11) 0.018(5) Uiso 1 d . . .
H17 H 0.4445(14) 0.079(2) 0.1763(11) 0.021(5) Uiso 1 d . . .
H18 H 0.4918(15) 0.067(3) 0.0571(11) 0.030(6) Uiso 1 d . . .
H19 H 0.4696(15) 0.277(2) -0.0163(12) 0.027(6) Uiso 1 d . . .
H20 H 0.4023(13) 0.495(2) 0.0284(10) 0.013(5) Uiso 1 d . . .
H22 H 0.4002(14) 0.512(2) 0.3025(11) 0.021(5) Uiso 1 d . . .
H23 H 0.5228(15) 0.605(3) 0.3722(12) 0.031(6) Uiso 1 d . . .
H24 H 0.6218(15) 0.793(2) 0.3284(11) 0.026(6) Uiso 1 d . . .
H25 H 0.5968(14) 0.889(2) 0.2149(10) 0.021(5) Uiso 1 d . . .
H26 H 0.4731(13) 0.797(2) 0.1466(10) 0.014(5) Uiso 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
Cl1 0.0343(3) 0.0420(3) 0.0219(3) 0.0040(2) 0.0022(2) 0.0040(2)
Cl2 0.0365(3) 0.0307(3) 0.0401(3) 0.0057(2) 0.0106(2) 0.0020(2)
C1S 0.0221(10) 0.0334(13) 0.0345(13) 0.0028(10) 0.0027(9) 0.0061(10)
O1 0.0162(6) 0.0105(6) 0.0108(6) 0.0016(5) 0.0016(5) 0.0020(5)
O2 0.0201(6) 0.0145(6) 0.0122(6) -0.0014(5) 0.0032(5) 0.0022(5)
N1 0.0145(7) 0.0122(8) 0.0113(7) 0.0011(6) 0.0013(6) 0.0017(6)
C1 0.0142(8) 0.0142(9) 0.0203(9) 0.0013(8) 0.0013(7) -0.0037(7)
C2 0.0138(8) 0.0152(9) 0.0168(9) -0.0010(7) -0.0018(7) -0.0040(7)
C3 0.0181(9) 0.0250(10) 0.0185(10) -0.0037(8) 0.0019(7) -0.0034(8)
C4 0.0237(10) 0.0424(13) 0.0162(10) 0.0045(9) 0.0000(8) -0.0064(9)
C5 0.0220(10) 0.0371(13) 0.0283(11) 0.0135(10) -0.0064(9) 0.0004(9)
C6 0.0191(10) 0.0307(12) 0.0289(11) 0.0008(9) -0.0009(8) 0.0072(9)
C7 0.0182(9) 0.0258(10) 0.0149(9) -0.0009(8) 0.0007(7) 0.0001(8)
C8 0.0125(8) 0.0099(8) 0.0133(8) -0.0007(7) 0.0002(6) -0.0028(6)
C9 0.0116(8) 0.0127(8) 0.0135(8) 0.0013(7) 0.0002(6) 0.0001(6)
C10 0.0255(10) 0.0170(10) 0.0162(9) 0.0017(8) 0.0031(7) 0.0050(8)
C11 0.0356(11) 0.0305(12) 0.0127(10) 0.0040(9) 0.0035(8) 0.0071(9)
C12 0.0264(10) 0.0250(11) 0.0209(10) 0.0113(9) -0.0011(8) 0.0034(8)
C13 0.0236(10) 0.0158(10) 0.0269(11) 0.0061(8) -0.0018(8) 0.0050(8)
C14 0.0195(9) 0.0154(9) 0.0175(9) 0.0002(7) 0.0013(7) 0.0008(7)
C15 0.0103(8) 0.0123(8) 0.0133(8) -0.0006(7) -0.0001(6) -0.0013(6)
C16 0.0170(9) 0.0152(9) 0.0147(9) -0.0009(7) 0.0015(7) 0.0007(7)
C17 0.0205(9) 0.0128(9) 0.0228(10) 0.0019(8) -0.0018(7) 0.0015(7)
C18 0.0211(10) 0.0155(10) 0.0274(11) -0.0083(8) 0.0035(8) 0.0035(8)
C19 0.0266(10) 0.0222(11) 0.0185(10) -0.0051(8) 0.0073(8) 0.0017(8)
C20 0.0203(9) 0.0154(9) 0.0146(9) 0.0008(8) 0.0026(7) -0.0001(7)
C21 0.0132(8) 0.0113(8) 0.0132(8) -0.0028(7) 0.0032(6) 0.0030(7)
C22 0.0175(9) 0.0157(9) 0.0139(9) -0.0019(7) 0.0033(7) 0.0004(7)
C23 0.0226(10) 0.0273(11) 0.0126(9) -0.0029(8) -0.0011(7) -0.0009(8)
C24 0.0179(9) 0.0295(11) 0.0206(10) -0.0080(9) -0.0013(8) -0.0046(8)
C25 0.0156(9) 0.0189(10) 0.0248(10) -0.0037(8) 0.0056(7) -0.0052(8)
C26 0.0176(9) 0.0136(9) 0.0149(9) 0.0000(7) 0.0032(7) 0.0015(7)
B1 0.0131(9) 0.0117(9) 0.0100(9) 0.0015(7) 0.0021(7) 0.0001(7)
_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
Cl1 C1S 1.766(2) . ?
Cl2 C1S 1.765(2) . ?
C1S H1SA 0.99(2) . ?
C1S H1SB 0.95(3) . ?
O1 C8 1.309(2) . ?
O1 B1 1.504(2) . ?
O2 C8 1.230(2) . ?
N1 C1 1.509(2) . ?
N1 B1 1.617(2) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.89(2) . ?
C1 C2 1.501(3) . ?
C1 H1C 0.971(19) . ?
C1 H1D 0.97(2) . ?
C2 C3 1.392(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.95(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.94(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.93(2) . ?
C7 H7 0.95(2) . ?
C8 C9 1.486(2) . ?
C9 C10 1.389(2) . ?
C9 C14 1.393(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.378(3) . ?
C11 H11 0.95(2) . ?
C12 C13 1.381(3) . ?
C12 H12 0.97(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.98(2) . ?
C14 H14 0.95(2) . ?
C15 C16 1.402(2) . ?
C15 C20 1.396(2) . ?
C15 B1 1.608(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.95(2) . ?
C17 C18 1.383(3) . ?
C17 H17 0.97(2) . ?
C18 C19 1.381(3) . ?
C18 H18 0.96(2) . ?
C19 C20 1.390(3) . ?
C19 H19 0.95(2) . ?
C20 H20 0.966(19) . ?
C21 C22 1.401(2) . ?
C21 C26 1.401(2) . ?
C21 B1 1.616(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.96(2) . ?
C23 C24 1.379(3) . ?
C23 H23 0.96(2) . ?
C24 C25 1.389(3) . ?
C24 H24 0.95(2) . ?
C25 C26 1.387(3) . ?
C25 H25 0.96(2) . ?
C26 H26 0.929(19) . ?
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
Cl1 C1S H1SA 104.2(13) . . ?
Cl1 C1S H1SB 108.3(15) . . ?
Cl2 C1S Cl1 111.76(12) . . ?
Cl2 C1S H1SA 110.2(13) . . ?
Cl2 C1S H1SB 106.4(15) . . ?
H1SA C1S H1SB 116(2) . . ?
C8 O1 B1 122.30(13) . . ?
C1 N1 B1 118.55(14) . . ?
C1 N1 H1A 108.2(13) . . ?
C1 N1 H1B 106.0(14) . . ?
B1 N1 H1A 105.6(13) . . ?
B1 N1 H1B 109.9(14) . . ?
H1A N1 H1B 108.3(19) . . ?
N1 C1 H1C 106.2(11) . . ?
N1 C1 H1D 107.0(11) . . ?
C2 C1 N1 112.74(15) . . ?
C2 C1 H1C 111.0(11) . . ?
C2 C1 H1D 110.4(11) . . ?
H1C C1 H1D 109.3(16) . . ?
C3 C2 C1 121.02(17) . . ?
C7 C2 C1 120.35(17) . . ?
C7 C2 C3 118.63(17) . . ?
C2 C3 H3 119.4(13) . . ?
C4 C3 C2 120.60(19) . . ?
C4 C3 H3 119.9(13) . . ?
C3 C4 C5 120.18(19) . . ?
C3 C4 H4 118.9(13) . . ?
C5 C4 H4 120.9(13) . . ?
C4 C5 H5 119.5(14) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.5(14) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 118.5(15) . . ?
C7 C6 H6 121.6(15) . . ?
C2 C7 H7 120.3(12) . . ?
C6 C7 C2 120.70(18) . . ?
C6 C7 H7 119.0(12) . . ?
O1 C8 C9 114.21(14) . . ?
O2 C8 O1 123.55(15) . . ?
O2 C8 C9 122.23(15) . . ?
C10 C9 C8 121.14(16) . . ?
C10 C9 C14 119.43(16) . . ?
C14 C9 C8 119.43(15) . . ?
C9 C10 H10 118.6(12) . . ?
C11 C10 C9 120.14(18) . . ?
C11 C10 H10 121.3(12) . . ?
C10 C11 H11 120.2(15) . . ?
C12 C11 C10 120.15(19) . . ?
C12 C11 H11 119.6(14) . . ?
C11 C12 C13 120.18(18) . . ?
C11 C12 H12 119.0(14) . . ?
C13 C12 H12 120.8(14) . . ?
C12 C13 C14 120.08(18) . . ?
C12 C13 H13 119.0(12) . . ?
C14 C13 H13 120.9(12) . . ?
C9 C14 H14 119.8(13) . . ?
C13 C14 C9 120.01(17) . . ?
C13 C14 H14 120.2(13) . . ?
C16 C15 B1 120.60(15) . . ?
C20 C15 C16 116.38(16) . . ?
C20 C15 B1 122.83(16) . . ?
C15 C16 H16 119.5(12) . . ?
C17 C16 C15 122.41(17) . . ?
C17 C16 H16 118.1(12) . . ?
C16 C17 H17 120.5(12) . . ?
C18 C17 C16 119.74(18) . . ?
C18 C17 H17 119.7(12) . . ?
C17 C18 H18 120.6(13) . . ?
C19 C18 C17 119.40(18) . . ?
C19 C18 H18 120.0(13) . . ?
C18 C19 C20 120.48(18) . . ?
C18 C19 H19 121.0(13) . . ?
C20 C19 H19 118.5(13) . . ?
C15 C20 H20 117.8(11) . . ?
C19 C20 C15 121.58(18) . . ?
C19 C20 H20 120.5(11) . . ?
C22 C21 B1 123.17(15) . . ?
C26 C21 C22 116.32(16) . . ?
C26 C21 B1 120.11(15) . . ?
C21 C22 H22 119.6(12) . . ?
C23 C22 C21 121.85(17) . . ?
C23 C22 H22 118.5(12) . . ?
C22 C23 H23 119.8(13) . . ?
C24 C23 C22 120.26(18) . . ?
C24 C23 H23 119.9(13) . . ?
C23 C24 C25 119.45(18) . . ?
C23 C24 H24 120.5(13) . . ?
C25 C24 H24 120.0(13) . . ?
C24 C25 H25 119.5(12) . . ?
C26 C25 C24 119.89(18) . . ?
C26 C25 H25 120.6(12) . . ?
C21 C26 H26 119.1(12) . . ?
C25 C26 C21 122.23(18) . . ?
C25 C26 H26 118.7(12) . . ?
O1 B1 N1 107.41(13) . . ?
O1 B1 C15 108.34(13) . . ?
O1 B1 C21 110.98(14) . . ?
C15 B1 N1 109.39(14) . . ?
C15 B1 C21 110.79(14) . . ?
C21 B1 N1 109.86(13) . . ?
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
N1 H1A O2 0.89(2) 2.17(2) 2.829(2) 130.5(17) .
N1 H1B O2 0.89(2) 2.01(2) 2.875(2) 164(2) 2_545
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
C1 N1 B1 O1 66.27(19) . . . . ?
C3 C2 C1 N1 95.7(2) . . . . ?
C7 C2 C1 N1 -83.6(2) . . . . ?
C8 O1 B1 N1 55.78(19) . . . . ?
C15 B1 O1 C8 173.84(13) . . . . ?
C15 B1 N1 C1 -51.1(2) . . . . ?
C15 B1 C21 C22 -75.9(2) . . . . ?
C15 B1 C21 C26 96.63(18) . . . . ?
C16 C15 B1 O1 -171.34(14) . . . . ?
C16 C15 B1 N1 -54.5(2) . . . . ?
C20 C15 B1 O1 14.0(2) . . . . ?
C20 C15 B1 N1 130.75(17) . . . . ?
C21 B1 O1 C8 -64.32(18) . . . . ?
C21 B1 N1 C1 -172.92(14) . . . . ?
C21 B1 C15 C16 66.7(2) . . . . ?
C21 B1 C15 C20 -108.00(18) . . . . ?
C22 C21 B1 O1 163.67(15) . . . . ?
C22 C21 B1 N1 45.0(2) . . . . ?
C26 C21 B1 O1 -23.8(2) . . . . ?
C26 C21 B1 N1 -142.39(16) . . . . ?
B1 N1 C1 C2 -78.95(19) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
TITL 15srv050 in P21/n #14
REM reset to P21/n #14
CELL 0.71073 14.1158 8.9604 18.8756 90 90.0788 90
ZERR 4 0.0003 0.0002 0.0004 0 0.0017 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H B Cl N O
UNIT 108 104 4 8 4 8
EQIV $1 0.5-X,-0.5+Y,0.5-Z
L.S. 9
PLAN 3
SIZE 0.32 0.11 0.1
TEMP -153.15
CONF C3 C2 C1 N1
CONF C7 C2 C1 N1
CONF B1 N1 C1 C2
CONF C1 N1 B1 O1
CONF C15 B1 N1 C1
CONF C21 B1 N1 C1
CONF C8 O1 B1 N1
CONF C15 B1 O1 C8
CONF C21 B1 O1 C8
CONF C16 C15 B1 O1
CONF C16 C15 B1 N1
CONF C21 B1 C15 C16
CONF C20 C15 B1 O1
CONF C20 C15 B1 N1
CONF C21 B1 C15 C20
CONF C26 C21 B1 O1
CONF C26 C21 B1 N1
CONF C15 B1 C21 C26
CONF C22 C21 B1 O1
CONF C22 C21 B1 N1
CONF C15 B1 C21 C22
HTAB N1 O2
HTAB N1 O2_$1
BOND $h
fmap 2 53
acta
OMIT -2 58
REM
REM
REM
WGHT 0.040000 1.320000
FVAR 0.15342
CL1 4 0.669089 0.301238 0.240534 11.00000 0.03429 0.04198 =
0.02194 0.00404 0.00218 0.00395
CL2 4 0.727125 0.513586 0.131381 11.00000 0.03648 0.03072 =
0.04011 0.00573 0.01058 0.00202
C1S 1 0.630969 0.434377 0.177696 11.00000 0.02206 0.03338 =
0.03453 0.00276 0.00271 0.00609
H1SA 2 0.590346 0.377012 0.144951 11.00000 0.03271
H1SB 2 0.601279 0.513615 0.202185 11.00000 0.04226
O1 6 0.320068 0.679431 0.103431 11.00000 0.01616 0.01046 =
0.01082 0.00164 0.00160 0.00201
O2 6 0.249816 0.849305 0.172541 11.00000 0.02007 0.01452 =
0.01223 -0.00144 0.00318 0.00219
N1 5 0.246248 0.541379 0.205470 11.00000 0.01450 0.01218 =
0.01133 0.00109 0.00129 0.00174
C1 1 0.168025 0.457516 0.168148 11.00000 0.01421 0.01418 =
0.02033 0.00125 0.00133 -0.00374
C2 1 0.112250 0.554442 0.118411 11.00000 0.01384 0.01524 =
0.01678 -0.00102 -0.00179 -0.00401
C3 1 0.133717 0.559863 0.046518 11.00000 0.01815 0.02498 =
0.01849 -0.00368 0.00188 -0.00339
C4 1 0.083727 0.652071 0.001595 11.00000 0.02371 0.04245 =
0.01616 0.00452 0.00003 -0.00640
C5 1 0.012133 0.741189 0.027642 11.00000 0.02197 0.03708 =
0.02832 0.01352 -0.00643 0.00044
C6 1 -0.010755 0.735825 0.098552 11.00000 0.01908 0.03066 =
0.02894 0.00084 -0.00094 0.00719
C7 1 0.038671 0.641868 0.143595 11.00000 0.01819 0.02579 =
0.01488 -0.00086 0.00067 0.00007
C8 1 0.279205 0.808503 0.114362 11.00000 0.01253 0.00985 =
0.01328 -0.00066 0.00017 -0.00282
C9 1 0.269558 0.902240 0.049815 11.00000 0.01160 0.01267 =
0.01353 0.00129 0.00015 0.00006
C10 1 0.296897 0.849238 -0.016194 11.00000 0.02546 0.01699 =
0.01621 0.00170 0.00314 0.00504
C11 1 0.287674 0.938736 -0.075532 11.00000 0.03557 0.03053 =
0.01271 0.00403 0.00349 0.00707
C12 1 0.252376 1.081526 -0.069261 11.00000 0.02642 0.02499 =
0.02087 0.01130 -0.00114 0.00342
C13 1 0.225004 1.135387 -0.003847 11.00000 0.02362 0.01583 =
0.02694 0.00612 -0.00184 0.00504
C14 1 0.232992 1.046101 0.055687 11.00000 0.01946 0.01537 =
0.01749 0.00017 0.00133 0.00084
C15 1 0.381994 0.420732 0.129105 11.00000 0.01032 0.01230 =
0.01335 -0.00062 -0.00012 -0.00132
C16 1 0.397095 0.294978 0.171805 11.00000 0.01702 0.01522 =
0.01469 -0.00086 0.00148 0.00068
C17 1 0.436628 0.164686 0.145875 11.00000 0.02050 0.01281 =
0.02276 0.00185 -0.00185 0.00151
C18 1 0.463828 0.156576 0.075600 11.00000 0.02111 0.01550 =
0.02743 -0.00829 0.00346 0.00352
C19 1 0.450227 0.278519 0.032037 11.00000 0.02665 0.02221 =
0.01852 -0.00507 0.00730 0.00171
C20 1 0.409347 0.408282 0.058289 11.00000 0.02031 0.01540 =
0.01458 0.00077 0.00265 -0.00006
C21 1 0.421066 0.645681 0.215800 11.00000 0.01320 0.01134 =
0.01320 -0.00282 0.00319 0.00299
C22 1 0.438706 0.590590 0.284018 11.00000 0.01754 0.01571 =
0.01391 -0.00194 0.00334 0.00043
C23 1 0.512645 0.644613 0.325572 11.00000 0.02262 0.02728 =
0.01258 -0.00293 -0.00114 -0.00090
C24 1 0.571613 0.754761 0.299952 11.00000 0.01790 0.02951 =
0.02056 -0.00796 -0.00126 -0.00456
C25 1 0.556178 0.812013 0.232560 11.00000 0.01558 0.01894 =
0.02485 -0.00367 0.00556 -0.00524
C26 1 0.482277 0.757593 0.191561 11.00000 0.01758 0.01356 =
0.01490 -0.00003 0.00322 0.00146
B1 3 0.343385 0.573819 0.162894 11.00000 0.01314 0.01173 =
0.00996 0.00154 0.00209 0.00011
H1A 2 0.224091 0.630382 0.217825 11.00000 0.01733
H1B 2 0.258592 0.490339 0.244567 11.00000 0.02678
H1C 2 0.127772 0.417074 0.205141 11.00000 0.01208
H1D 2 0.197538 0.376103 0.142495 11.00000 0.01466
H3 2 0.184459 0.500289 0.028493 11.00000 0.02739
H4 2 0.099873 0.653826 -0.047295 11.00000 0.02644
H5 2 -0.021236 0.803980 -0.003309 11.00000 0.02983
H6 2 -0.060419 0.795146 0.114787 11.00000 0.03959
H7 2 0.021598 0.638220 0.192054 11.00000 0.02164
H10 2 0.320406 0.752727 -0.019470 11.00000 0.01375
H11 2 0.303380 0.900632 -0.121187 11.00000 0.03854
H12 2 0.248389 1.143492 -0.110980 11.00000 0.03416
H13 2 0.201580 1.238170 -0.000211 11.00000 0.02502
H14 2 0.212719 1.081786 0.100312 11.00000 0.02177
H16 2 0.380837 0.298818 0.220847 11.00000 0.01807
H17 2 0.444520 0.078592 0.176349 11.00000 0.02111
H18 2 0.491830 0.067197 0.057069 11.00000 0.03021
H19 2 0.469643 0.276595 -0.016278 11.00000 0.02692
H20 2 0.402323 0.495136 0.028411 11.00000 0.01312
H22 2 0.400173 0.511913 0.302464 11.00000 0.02126
H23 2 0.522788 0.604669 0.372244 11.00000 0.03138
H24 2 0.621807 0.792719 0.328367 11.00000 0.02596
H25 2 0.596761 0.888711 0.214903 11.00000 0.02061
H26 2 0.473090 0.797137 0.146557 11.00000 0.01394
HKLF 4
REM 15srv050 in P21/n #14
REM R1 = 0.0488 for 4421 Fo > 4sig(Fo) and 0.0883 for all 6345 data
REM 402 parameters refined using 0 restraints
END
WGHT 0.0378 1.3192
REM Highest difference peak 0.351, deepest hole -0.387, 1-sigma level 0.061
Q1 1 0.3811 0.5115 0.1430 11.00000 0.05 0.35
Q2 1 0.2648 0.8613 0.0783 11.00000 0.05 0.32
Q3 1 0.2856 0.8780 0.0198 11.00000 0.05 0.31
REM The information below was added by Olex2.
REM
REM R1 = 0.0488 for 4421 Fo > 4sig(Fo) and 0.0883 for all 42072 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.35, deepest hole -0.39
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0883
REM R1_gt = 0.0488
REM wR_ref = 0.1105
REM GOOF = 1.015
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 42072
REM Reflections_gt = 4421
REM Parameters = n/a
REM Hole = -0.39
REM Peak = 0.35
REM Flack = n/a
;
#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_5a_14srv256
_database_code_depnum_ccdc_archive 'CCDC 1551616'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2014-11-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_chemical_name_common ?
_chemical_name_systematic
; Bis(3,4,5-trifluorophenyl)-borinic acid benzylamine-4'-phenylbutanoate
;
_chemical_formula_moiety 'C29 H24 B F6 N O2'
_chemical_formula_sum 'C29 H24 B F6 N O2'
_chemical_formula_weight 543.30
_chemical_melting_point 435.7(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.0140(3)
_cell_length_b 11.7859(4)
_cell_length_c 23.0748(7)
_cell_angle_alpha 103.8183(8)
_cell_angle_beta 98.0649(10)
_cell_angle_gamma 96.9376(9)
_cell_volume 2584.47(14)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9993
_cell_measurement_temperature 120
_cell_measurement_theta_max 75.22
_cell_measurement_theta_min 3.90
_shelx_estimated_absorpt_T_max 0.869
_shelx_estimated_absorpt_T_min 0.806
_exptl_absorpt_coefficient_mu 0.996
_exptl_absorpt_correction_T_max 0.8688
_exptl_absorpt_correction_T_min 0.7120
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0890 after correction.
The Ratio of minimum to maximum transmission is 0.8195.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.396
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 1.00 1.00 0.1010
2.00 -1.00 -1.00 0.1120
-1.00 1.00 -1.00 0.1020
0.00 0.00 1.00 0.0800
0.00 0.00 -1.00 0.0980
-2.00 0.00 1.00 0.0850
2.00 0.00 -1.00 0.1060
0.00 -2.00 -1.00 0.0700
0.00 2.00 1.00 0.0720
0.00 -1.00 3.00 0.0770
0.00 1.00 -3.00 0.0970
-2.00 -1.00 3.00 0.0940
1.00 3.00 -3.00 0.1040
_exptl_crystal_size_max 0.226
_exptl_crystal_size_mid 0.207
_exptl_crystal_size_min 0.145
_exptl_special_details
;
The data collection nominally covered full sphere of reciprocal
space, by a combination of 9 runs of narrow-frame \w-scans (scan
width 0.5\% \w, 10s exposure for low, 20s for medium and 30s for
high \q), every run at a different 2\q and/or \f angle.
Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0574
_diffrn_reflns_av_unetI/netI 0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 21248
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full 65.997
_diffrn_reflns_theta_max 65.997
_diffrn_reflns_theta_min 3.905
_diffrn_ambient_temperature 120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'ImuS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 7740
_reflns_number_total 8496
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.388
_refine_diff_density_min -0.259
_refine_diff_density_rms 0.074
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 719
_refine_ls_number_reflns 8496
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0608
_refine_ls_R_factor_gt 0.0579
_refine_ls_restrained_S_all 1.035
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1070P)^2^+0.4700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1578
_refine_ls_wR_factor_ref 0.1626
_refine_special_details
'Amino H atoms - refall, other H - constr (riding)'
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B), C2'(H2A',H2B'),
C3'(H3A',H3B'), C4'(H4A',H4B'), C23'(H1,H2)
2.b Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C18(H18),
C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C6'(H6'), C7'(H7'),
C8'(H8'), C9'(H9'), C10'(H10'), C12'(H12'), C16'(H16'), C18'(H18'),
C22'(H22'), C25'(H25'), C26'(H26'), C27'(H27'), C28'(H28'), C29'(H29')
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24480(17) 0.48823(12) 0.50597(6) 0.0719(4) Uani 1 1 d . . . . .
F2 F 0.13628(13) 0.66036(13) 0.57276(5) 0.0624(4) Uani 1 1 d . . . . .
F3 F 0.16138(13) 0.87693(13) 0.55169(6) 0.0631(4) Uani 1 1 d . . . . .
F4 F 0.88829(12) 0.79527(12) 0.49135(5) 0.0580(3) Uani 1 1 d . . . . .
F5 F 0.94716(11) 0.60683(11) 0.41157(5) 0.0505(3) Uani 1 1 d . . . . .
F6 F 0.75337(11) 0.48118(9) 0.31670(5) 0.0442(3) Uani 1 1 d . . . . .
O1 O 0.42524(12) 0.87920(10) 0.38758(5) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.51916(13) 0.88720(11) 0.30581(5) 0.0393(3) Uani 1 1 d . . . . .
N N 0.32194(14) 0.67931(13) 0.31720(6) 0.0301(3) Uani 1 1 d . . . . .
HA H 0.369(2) 0.6723(18) 0.2860(10) 0.039(5) Uiso 1 1 d . . . . .
HB H 0.3000(19) 0.6062(18) 0.3178(8) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.47792(17) 0.93574(15) 0.35088(7) 0.0323(4) Uani 1 1 d . . . . .
C2 C 0.47587(18) 1.06655(15) 0.37177(8) 0.0350(4) Uani 1 1 d . . . . .
H2A H 0.5247 1.0959 0.4142 0.042 Uiso 1 1 calc R . . . .
H2B H 0.3798 1.0791 0.3715 0.042 Uiso 1 1 calc R . . . .
C3 C 0.54008(19) 1.13984(15) 0.33378(8) 0.0383(4) Uani 1 1 d . . . . .
H3A H 0.4955 1.1080 0.2908 0.046 Uiso 1 1 calc R . . . .
H3B H 0.6381 1.1326 0.3364 0.046 Uiso 1 1 calc R . . . .
C4 C 0.52644(19) 1.27141(15) 0.35462(9) 0.0409(4) Uani 1 1 d . . . . .
H4A H 0.5623 1.3007 0.3986 0.049 Uiso 1 1 calc R . . . .
H4B H 0.5835 1.3169 0.3335 0.049 Uiso 1 1 calc R . . . .
C5 C 0.38198(19) 1.29458(14) 0.34266(8) 0.0373(4) Uani 1 1 d . . . . .
C6 C 0.2979(2) 1.29907(16) 0.38621(9) 0.0421(4) Uani 1 1 d . . . . .
H6 H 0.3330 1.2896 0.4249 0.051 Uiso 1 1 calc R . . . .
C7 C 0.1636(2) 1.31720(17) 0.37380(10) 0.0500(5) Uani 1 1 d . . . . .
H7 H 0.1074 1.3193 0.4038 0.060 Uiso 1 1 calc R . . . .
C8 C 0.1112(2) 1.33228(18) 0.31793(11) 0.0550(5) Uani 1 1 d . . . . .
H8 H 0.0194 1.3451 0.3096 0.066 Uiso 1 1 calc R . . . .
C9 C 0.1935(2) 1.32864(19) 0.27425(10) 0.0533(5) Uani 1 1 d . . . . .
H9 H 0.1582 1.3390 0.2358 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3270(2) 1.30988(17) 0.28659(9) 0.0453(4) Uani 1 1 d . . . . .
H10 H 0.3824 1.3074 0.2562 0.054 Uiso 1 1 calc R . . . .
C11 C 0.33476(17) 0.72506(15) 0.43491(7) 0.0334(4) Uani 1 1 d . . . . .
C12 C 0.3228(2) 0.61441(17) 0.44727(8) 0.0412(4) Uani 1 1 d . . . . .
H12 H 0.3618 0.5528 0.4243 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2543(2) 0.59399(18) 0.49275(9) 0.0465(5) Uani 1 1 d . . . . .
C14 C 0.19805(19) 0.68109(19) 0.52737(8) 0.0447(5) Uani 1 1 d . . . . .
C15 C 0.21139(19) 0.79007(19) 0.51592(8) 0.0449(5) Uani 1 1 d . . . . .
C16 C 0.27714(18) 0.81270(17) 0.47010(8) 0.0389(4) Uani 1 1 d . . . . .
H16 H 0.2830 0.8888 0.4626 0.047 Uiso 1 1 calc R . . . .
C17 C 0.56258(17) 0.70636(14) 0.38679(7) 0.0317(4) Uani 1 1 d . . . . .
C18 C 0.66460(19) 0.76898(16) 0.43595(8) 0.0385(4) Uani 1 1 d . . . . .
H18 H 0.6463 0.8360 0.4641 0.046 Uiso 1 1 calc R . . . .
C19 C 0.79074(19) 0.73448(18) 0.44390(8) 0.0410(4) Uani 1 1 d . . . . .
C20 C 0.82270(18) 0.63843(17) 0.40381(8) 0.0392(4) Uani 1 1 d . . . . .
C21 C 0.72280(18) 0.57576(15) 0.35598(8) 0.0357(4) Uani 1 1 d . . . . .
C22 C 0.59478(17) 0.60781(15) 0.34693(8) 0.0329(4) Uani 1 1 d . . . . .
H22 H 0.5280 0.5626 0.3134 0.040 Uiso 1 1 calc R . . . .
C23 C 0.19275(18) 0.72610(15) 0.30034(8) 0.0370(4) Uani 1 1 d . . . . .
H23A H 0.2162 0.8053 0.2935 0.044 Uiso 1 1 calc R . . . .
H23B H 0.1409 0.7347 0.3342 0.044 Uiso 1 1 calc R . . . .
C24 C 0.10486(17) 0.64444(15) 0.24392(8) 0.0326(4) Uani 1 1 d . . . . .
C25 C 0.00726(17) 0.55469(16) 0.24873(8) 0.0368(4) Uani 1 1 d . . . . .
H25 H -0.0074 0.5480 0.2877 0.044 Uiso 1 1 calc R . . . .
C26 C -0.06926(18) 0.47450(16) 0.19719(9) 0.0418(4) Uani 1 1 d . . . . .
H26 H -0.1345 0.4122 0.2009 0.050 Uiso 1 1 calc R . . . .
C27 C -0.05032(19) 0.48559(16) 0.14045(9) 0.0413(4) Uani 1 1 d . . . . .
H27 H -0.1025 0.4307 0.1051 0.050 Uiso 1 1 calc R . . . .
C28 C 0.04457(19) 0.57657(16) 0.13511(8) 0.0395(4) Uani 1 1 d . . . . .
H28 H 0.0564 0.5848 0.0961 0.047 Uiso 1 1 calc R . . . .
C29 C 0.12240(17) 0.65564(15) 0.18658(8) 0.0356(4) Uani 1 1 d . . . . .
H29 H 0.1879 0.7176 0.1827 0.043 Uiso 1 1 calc R . . . .
B B 0.4153(2) 0.74968(17) 0.38166(8) 0.0327(4) Uani 1 1 d . . . . .
F1' F 0.25138(12) 1.05041(10) 0.18245(5) 0.0503(3) Uani 1 1 d . . . . .
F2' F 0.05822(11) 0.93009(11) 0.08607(5) 0.0488(3) Uani 1 1 d . . . . .
F3' F 0.10530(11) 0.72983(11) 0.01147(5) 0.0518(3) Uani 1 1 d . . . . .
F4' F 0.84299(12) 0.57361(11) -0.02138(5) 0.0534(3) Uani 1 1 d . . . . .
F5' F 0.86203(12) 0.76710(12) -0.06564(5) 0.0548(3) Uani 1 1 d . . . . .
F6' F 0.74532(13) 0.95345(11) -0.01713(5) 0.0559(3) Uani 1 1 d . . . . .
O1' O 0.53163(12) 0.62123(10) 0.12675(5) 0.0317(3) Uani 1 1 d . . . . .
O2' O 0.45189(13) 0.65056(11) 0.21362(5) 0.0386(3) Uani 1 1 d . . . . .
N' N 0.65802(15) 0.81929(12) 0.19345(6) 0.0305(3) Uani 1 1 d . . . . .
HA' H 0.688(2) 0.8945(19) 0.1938(8) 0.032(5) Uiso 1 1 d . . . . .
HB' H 0.610(2) 0.8256(19) 0.2225(10) 0.043(6) Uiso 1 1 d . . . . .
C1' C 0.46783(16) 0.58439(15) 0.16691(7) 0.0322(4) Uani 1 1 d . . . . .
C2' C 0.42329(17) 0.45254(15) 0.14947(8) 0.0366(4) Uani 1 1 d . . . . .
H2A' H 0.3766 0.4261 0.1066 0.044 Uiso 1 1 calc R . . . .
H2B' H 0.3579 0.4314 0.1751 0.044 Uiso 1 1 calc R . . . .
C3' C 0.54762(17) 0.39042(15) 0.15774(8) 0.0359(4) Uani 1 1 d . . . . .
H3A' H 0.5865 0.4098 0.2015 0.043 Uiso 1 1 calc R . . . .
H3B' H 0.6181 0.4216 0.1370 0.043 Uiso 1 1 calc R . . . .
C4' C 0.51494(18) 0.25568(15) 0.13304(9) 0.0387(4) Uani 1 1 d . . . . .
H4A' H 0.4447 0.2233 0.1536 0.046 Uiso 1 1 calc R . . . .
H4B' H 0.4780 0.2351 0.0891 0.046 Uiso 1 1 calc R . . . .
C5' C 0.64255(18) 0.20201(14) 0.14367(8) 0.0356(4) Uani 1 1 d . . . . .
C6' C 0.68498(19) 0.17887(15) 0.19920(8) 0.0396(4) Uani 1 1 d . . . . .
H6' H 0.6282 0.1895 0.2292 0.048 Uiso 1 1 calc R . . . .
C7' C 0.8089(2) 0.14051(17) 0.21138(9) 0.0452(4) Uani 1 1 d . . . . .
H7' H 0.8364 0.1248 0.2494 0.054 Uiso 1 1 calc R . . . .
C8' C 0.8928(2) 0.12499(17) 0.16800(10) 0.0458(5) Uani 1 1 d . . . . .
H8' H 0.9785 0.1000 0.1765 0.055 Uiso 1 1 calc R . . . .
C9' C 0.8510(2) 0.14611(17) 0.11245(9) 0.0451(4) Uani 1 1 d . . . . .
H9' H 0.9076 0.1346 0.0824 0.054 Uiso 1 1 calc R . . . .
C10' C 0.72668(19) 0.18405(15) 0.10029(8) 0.0397(4) Uani 1 1 d . . . . .
H10' H 0.6987 0.1979 0.0619 0.048 Uiso 1 1 calc R . . . .
C11' C 0.42469(17) 0.80547(14) 0.12044(7) 0.0308(3) Uani 1 1 d . . . . .
C12' C 0.39825(17) 0.90919(15) 0.15796(8) 0.0336(4) Uani 1 1 d . . . . .
H12' H 0.4647 0.9521 0.1922 0.040 Uiso 1 1 calc R . . . .
C13' C 0.27635(19) 0.94999(15) 0.14580(8) 0.0371(4) Uani 1 1 d . . . . .
C14' C 0.17710(17) 0.89036(16) 0.09712(8) 0.0374(4) Uani 1 1 d . . . . .
C15' C 0.20266(18) 0.78802(17) 0.05955(8) 0.0371(4) Uani 1 1 d . . . . .
C16' C 0.32326(18) 0.74580(16) 0.07051(8) 0.0347(4) Uani 1 1 d . . . . .
H16' H 0.3381 0.6752 0.0439 0.042 Uiso 1 1 calc R . . . .
C17' C 0.65076(16) 0.75638(15) 0.07555(7) 0.0318(4) Uani 1 1 d . . . . .
C18' C 0.71362(18) 0.66176(16) 0.05038(8) 0.0361(4) Uani 1 1 d . . . . .
H18' H 0.7069 0.5931 0.0653 0.043 Uiso 1 1 calc R . . . .
C19' C 0.78553(18) 0.66684(17) 0.00403(8) 0.0408(4) Uani 1 1 d . . . . .
C20' C 0.79696(18) 0.76502(18) -0.01864(8) 0.0417(4) Uani 1 1 d . . . . .
C21' C 0.73641(19) 0.85938(17) 0.00653(8) 0.0406(4) Uani 1 1 d . . . . .
C22' C 0.66387(18) 0.85660(16) 0.05291(8) 0.0365(4) Uani 1 1 d . . . . .
H22' H 0.6228 0.9227 0.0695 0.044 Uiso 1 1 calc R . . . .
C23' C 0.78103(18) 0.76519(15) 0.21119(8) 0.0367(4) Uani 1 1 d . . . . .
H1 H 0.7510 0.6924 0.2233 0.044 Uiso 1 1 calc R . . . .
H2 H 0.8268 0.7426 0.1757 0.044 Uiso 1 1 calc R . . . .
C24' C 0.88117(17) 0.84908(14) 0.26265(8) 0.0326(4) Uani 1 1 d . . . . .
C25' C 0.86600(18) 0.85692(15) 0.32227(8) 0.0359(4) Uani 1 1 d . . . . .
H25' H 0.7923 0.8083 0.3307 0.043 Uiso 1 1 calc R . . . .
C26' C 0.9580(2) 0.93541(16) 0.36966(8) 0.0395(4) Uani 1 1 d . . . . .
H26' H 0.9484 0.9390 0.4104 0.047 Uiso 1 1 calc R . . . .
C27' C 1.06382(19) 1.00859(16) 0.35752(8) 0.0398(4) Uani 1 1 d . . . . .
H27' H 1.1259 1.0630 0.3900 0.048 Uiso 1 1 calc R . . . .
C28' C 1.07919(18) 1.00251(16) 0.29813(8) 0.0392(4) Uani 1 1 d . . . . .
H28' H 1.1509 1.0534 0.2898 0.047 Uiso 1 1 calc R . . . .
C29' C 0.98920(18) 0.92161(15) 0.25097(8) 0.0357(4) Uani 1 1 d . . . . .
H29' H 1.0014 0.9156 0.2103 0.043 Uiso 1 1 calc R . . . .
B' B 0.56349(19) 0.75015(16) 0.12903(8) 0.0307(4) 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 0.1108(12) 0.0570(8) 0.0622(8) 0.0309(7) 0.0401(8) 0.0084(8)
F2 0.0534(7) 0.0934(10) 0.0436(6) 0.0208(6) 0.0218(5) 0.0027(7)
F3 0.0591(8) 0.0791(9) 0.0530(7) 0.0041(6) 0.0244(6) 0.0286(7)
F4 0.0416(6) 0.0776(9) 0.0435(6) 0.0061(6) -0.0083(5) 0.0040(6)
F5 0.0321(6) 0.0666(7) 0.0570(7) 0.0243(6) 0.0038(5) 0.0126(5)
F6 0.0374(6) 0.0406(6) 0.0570(7) 0.0118(5) 0.0141(5) 0.0108(4)
O1 0.0383(6) 0.0297(6) 0.0359(6) 0.0090(5) 0.0067(5) 0.0043(5)
O2 0.0479(7) 0.0341(6) 0.0375(7) 0.0097(5) 0.0113(6) 0.0073(5)
N 0.0305(7) 0.0293(8) 0.0313(7) 0.0087(6) 0.0058(6) 0.0062(6)
C1 0.0300(8) 0.0338(8) 0.0317(8) 0.0087(7) 0.0019(7) 0.0035(6)
C2 0.0358(9) 0.0331(9) 0.0349(9) 0.0073(7) 0.0057(7) 0.0046(7)
C3 0.0385(9) 0.0335(9) 0.0450(10) 0.0130(8) 0.0098(8) 0.0058(7)
C4 0.0390(10) 0.0330(9) 0.0495(10) 0.0116(8) 0.0050(8) 0.0024(7)
C5 0.0403(9) 0.0245(8) 0.0447(10) 0.0080(7) 0.0037(8) 0.0030(7)
C6 0.0484(11) 0.0317(9) 0.0452(10) 0.0096(7) 0.0065(8) 0.0049(7)
C7 0.0450(11) 0.0393(10) 0.0692(14) 0.0155(9) 0.0178(10) 0.0090(8)
C8 0.0409(11) 0.0410(11) 0.0818(16) 0.0185(10) 0.0006(10) 0.0079(8)
C9 0.0525(12) 0.0503(12) 0.0567(12) 0.0182(10) -0.0033(10) 0.0122(9)
C10 0.0518(11) 0.0392(10) 0.0467(10) 0.0138(8) 0.0087(9) 0.0094(8)
C11 0.0311(8) 0.0372(9) 0.0288(8) 0.0058(7) 0.0018(7) 0.0033(7)
C12 0.0510(11) 0.0386(9) 0.0353(9) 0.0100(7) 0.0123(8) 0.0057(8)
C13 0.0551(12) 0.0465(11) 0.0388(10) 0.0153(8) 0.0098(9) 0.0008(9)
C14 0.0368(10) 0.0662(13) 0.0310(9) 0.0144(9) 0.0085(8) 0.0007(9)
C15 0.0338(9) 0.0612(12) 0.0360(9) 0.0030(9) 0.0062(8) 0.0128(8)
C16 0.0354(9) 0.0426(10) 0.0372(9) 0.0073(8) 0.0046(7) 0.0087(7)
C17 0.0326(9) 0.0324(8) 0.0317(8) 0.0129(7) 0.0052(7) 0.0023(6)
C18 0.0391(10) 0.0413(9) 0.0339(9) 0.0100(7) 0.0047(7) 0.0037(7)
C19 0.0349(9) 0.0517(11) 0.0338(9) 0.0145(8) -0.0021(7) 0.0004(8)
C20 0.0301(9) 0.0487(10) 0.0456(10) 0.0248(8) 0.0069(8) 0.0075(7)
C21 0.0354(9) 0.0339(9) 0.0416(9) 0.0153(7) 0.0104(7) 0.0056(7)
C22 0.0319(8) 0.0324(8) 0.0362(9) 0.0137(7) 0.0060(7) 0.0022(6)
C23 0.0356(9) 0.0354(9) 0.0377(9) 0.0054(7) 0.0015(7) 0.0106(7)
C24 0.0296(8) 0.0319(8) 0.0375(9) 0.0081(7) 0.0058(7) 0.0118(6)
C25 0.0320(9) 0.0422(9) 0.0403(9) 0.0157(8) 0.0077(7) 0.0107(7)
C26 0.0335(9) 0.0385(9) 0.0526(11) 0.0147(8) 0.0033(8) 0.0022(7)
C27 0.0387(9) 0.0364(9) 0.0425(10) 0.0027(8) -0.0018(8) 0.0063(7)
C28 0.0422(10) 0.0428(10) 0.0342(9) 0.0083(7) 0.0085(8) 0.0116(8)
C29 0.0322(8) 0.0348(9) 0.0410(9) 0.0111(7) 0.0079(7) 0.0058(7)
B 0.0359(10) 0.0297(9) 0.0319(9) 0.0081(7) 0.0049(8) 0.0039(7)
F1' 0.0449(6) 0.0418(6) 0.0619(7) 0.0032(5) 0.0105(5) 0.0175(5)
F2' 0.0337(6) 0.0607(7) 0.0574(7) 0.0206(6) 0.0072(5) 0.0188(5)
F3' 0.0362(6) 0.0691(8) 0.0426(6) 0.0061(5) -0.0046(5) 0.0093(5)
F4' 0.0498(7) 0.0609(7) 0.0488(6) 0.0025(5) 0.0187(5) 0.0186(5)
F5' 0.0439(6) 0.0809(9) 0.0385(6) 0.0140(6) 0.0157(5) -0.0005(6)
F6' 0.0665(8) 0.0551(7) 0.0515(7) 0.0265(6) 0.0169(6) -0.0023(6)
O1' 0.0348(6) 0.0297(6) 0.0317(6) 0.0085(5) 0.0072(5) 0.0064(5)
O2' 0.0415(7) 0.0400(7) 0.0347(6) 0.0084(5) 0.0114(5) 0.0057(5)
N' 0.0299(7) 0.0291(8) 0.0327(7) 0.0081(6) 0.0050(6) 0.0061(6)
C1' 0.0281(8) 0.0349(9) 0.0355(9) 0.0129(7) 0.0040(7) 0.0068(6)
C2' 0.0317(9) 0.0362(9) 0.0423(9) 0.0124(7) 0.0049(7) 0.0048(7)
C3' 0.0324(9) 0.0352(9) 0.0388(9) 0.0092(7) 0.0031(7) 0.0049(7)
C4' 0.0344(9) 0.0338(9) 0.0460(10) 0.0088(7) 0.0038(8) 0.0050(7)
C5' 0.0353(9) 0.0265(8) 0.0435(9) 0.0080(7) 0.0060(7) 0.0025(7)
C6' 0.0424(10) 0.0346(9) 0.0453(10) 0.0132(8) 0.0123(8) 0.0079(7)
C7' 0.0477(11) 0.0417(10) 0.0482(11) 0.0159(8) 0.0039(9) 0.0110(8)
C8' 0.0373(10) 0.0387(10) 0.0625(12) 0.0139(9) 0.0072(9) 0.0102(8)
C9' 0.0425(10) 0.0379(10) 0.0562(11) 0.0103(8) 0.0175(9) 0.0057(8)
C10' 0.0439(10) 0.0344(9) 0.0409(10) 0.0105(7) 0.0084(8) 0.0042(7)
C11' 0.0314(8) 0.0323(8) 0.0313(8) 0.0127(7) 0.0074(7) 0.0043(6)
C12' 0.0307(8) 0.0332(8) 0.0366(9) 0.0090(7) 0.0049(7) 0.0049(7)
C13' 0.0382(9) 0.0328(9) 0.0434(10) 0.0111(7) 0.0128(8) 0.0092(7)
C14' 0.0286(9) 0.0466(10) 0.0444(10) 0.0211(8) 0.0098(7) 0.0116(7)
C15' 0.0314(9) 0.0464(10) 0.0323(9) 0.0124(7) 0.0015(7) 0.0022(7)
C16' 0.0333(9) 0.0372(9) 0.0339(9) 0.0089(7) 0.0066(7) 0.0064(7)
C17' 0.0285(8) 0.0354(8) 0.0301(8) 0.0086(7) 0.0020(6) 0.0030(6)
C18' 0.0342(9) 0.0402(9) 0.0335(9) 0.0094(7) 0.0044(7) 0.0060(7)
C19' 0.0339(9) 0.0502(11) 0.0347(9) 0.0024(8) 0.0066(7) 0.0087(8)
C20' 0.0309(9) 0.0603(12) 0.0309(9) 0.0095(8) 0.0070(7) -0.0014(8)
C21' 0.0382(9) 0.0465(10) 0.0364(9) 0.0159(8) 0.0044(7) -0.0039(8)
C22' 0.0342(9) 0.0385(9) 0.0354(9) 0.0096(7) 0.0053(7) 0.0020(7)
C23' 0.0359(9) 0.0338(9) 0.0378(9) 0.0050(7) 0.0007(7) 0.0107(7)
C24' 0.0318(8) 0.0296(8) 0.0370(9) 0.0083(7) 0.0033(7) 0.0115(6)
C25' 0.0350(9) 0.0338(9) 0.0401(9) 0.0103(7) 0.0082(7) 0.0068(7)
C26' 0.0463(10) 0.0379(9) 0.0342(9) 0.0076(7) 0.0078(8) 0.0095(8)
C27' 0.0398(10) 0.0334(9) 0.0414(10) 0.0047(7) -0.0001(8) 0.0054(7)
C28' 0.0344(9) 0.0365(9) 0.0478(10) 0.0130(8) 0.0072(8) 0.0056(7)
C29' 0.0353(9) 0.0379(9) 0.0369(9) 0.0122(7) 0.0071(7) 0.0118(7)
B' 0.0315(9) 0.0292(9) 0.0311(9) 0.0082(7) 0.0042(8) 0.0044(7)
_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 C13 1.348(2) . ?
F2 C14 1.344(2) . ?
F3 C15 1.348(2) . ?
F4 C19 1.350(2) . ?
F5 C20 1.344(2) . ?
F6 C21 1.355(2) . ?
O1 C1 1.323(2) . ?
O1 B 1.490(2) . ?
O2 C1 1.214(2) . ?
N C23 1.504(2) . ?
N B 1.615(2) . ?
C1 C2 1.505(2) . ?
C2 C3 1.521(2) . ?
C3 C4 1.539(2) . ?
C4 C5 1.504(3) . ?
C5 C6 1.394(3) . ?
C5 C10 1.395(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.382(3) . ?
C11 C12 1.395(3) . ?
C11 C16 1.391(2) . ?
C11 B 1.623(2) . ?
C12 C13 1.383(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.382(3) . ?
C17 C18 1.403(2) . ?
C17 C22 1.401(2) . ?
C17 B 1.616(3) . ?
C18 C19 1.374(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.374(3) . ?
C21 C22 1.382(2) . ?
C23 C24 1.507(2) . ?
C24 C25 1.387(2) . ?
C24 C29 1.394(2) . ?
C25 C26 1.388(3) . ?
C26 C27 1.383(3) . ?
C27 C28 1.385(3) . ?
C28 C29 1.387(3) . ?
F1' C13' 1.353(2) . ?
F2' C14' 1.345(2) . ?
F3' C15' 1.350(2) . ?
F4' C19' 1.350(2) . ?
F5' C20' 1.345(2) . ?
F6' C21' 1.347(2) . ?
O1' C1' 1.322(2) . ?
O1' B' 1.501(2) . ?
O2' C1' 1.213(2) . ?
N' C23' 1.505(2) . ?
N' B' 1.616(2) . ?
C1' C2' 1.503(2) . ?
C2' C3' 1.531(2) . ?
C3' C4' 1.531(2) . ?
C4' C5' 1.508(2) . ?
C5' C6' 1.392(3) . ?
C5' C10' 1.391(3) . ?
C6' C7' 1.386(3) . ?
C7' C8' 1.389(3) . ?
C8' C9' 1.381(3) . ?
C9' C10' 1.387(3) . ?
C11' C12' 1.397(2) . ?
C11' C16' 1.402(2) . ?
C11' B' 1.612(2) . ?
C12' C13' 1.382(2) . ?
C13' C14' 1.373(3) . ?
C14' C15' 1.382(3) . ?
C15' C16' 1.375(2) . ?
C17' C18' 1.393(2) . ?
C17' C22' 1.401(2) . ?
C17' B' 1.619(2) . ?
C18' C19' 1.379(3) . ?
C19' C20' 1.378(3) . ?
C20' C21' 1.377(3) . ?
C21' C22' 1.380(3) . ?
C23' C24' 1.503(2) . ?
C24' C25' 1.388(2) . ?
C24' C29' 1.394(2) . ?
C25' C26' 1.389(3) . ?
C26' C27' 1.387(3) . ?
C27' C28' 1.386(3) . ?
C28' C29' 1.388(3) . ?
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
C1 O1 B 125.27(13) . . ?
C23 N B 115.90(13) . . ?
O1 C1 C2 110.86(14) . . ?
O2 C1 O1 123.95(15) . . ?
O2 C1 C2 125.18(15) . . ?
C1 C2 C3 114.68(14) . . ?
C2 C3 C4 112.32(15) . . ?
C5 C4 C3 113.61(15) . . ?
C6 C5 C4 121.67(17) . . ?
C6 C5 C10 117.81(18) . . ?
C10 C5 C4 120.50(17) . . ?
C7 C6 C5 120.90(19) . . ?
C8 C7 C6 120.3(2) . . ?
C7 C8 C9 119.55(19) . . ?
C10 C9 C8 120.0(2) . . ?
C9 C10 C5 121.38(19) . . ?
C12 C11 B 120.50(15) . . ?
C16 C11 C12 117.75(16) . . ?
C16 C11 B 121.74(16) . . ?
C13 C12 C11 120.26(18) . . ?
F1 C13 C12 120.75(18) . . ?
F1 C13 C14 117.61(17) . . ?
C14 C13 C12 121.61(18) . . ?
F2 C14 C13 120.50(19) . . ?
F2 C14 C15 121.23(19) . . ?
C15 C14 C13 118.22(17) . . ?
F3 C15 C14 118.13(17) . . ?
F3 C15 C16 120.29(19) . . ?
C14 C15 C16 121.56(18) . . ?
C15 C16 C11 120.58(18) . . ?
C18 C17 B 117.92(15) . . ?
C22 C17 C18 117.23(16) . . ?
C22 C17 B 124.80(15) . . ?
C19 C18 C17 120.77(17) . . ?
F4 C19 C18 120.36(17) . . ?
F4 C19 C20 117.91(17) . . ?
C18 C19 C20 121.72(17) . . ?
F5 C20 C19 121.11(17) . . ?
F5 C20 C21 121.04(17) . . ?
C21 C20 C19 117.85(16) . . ?
F6 C21 C20 118.10(16) . . ?
F6 C21 C22 120.09(16) . . ?
C20 C21 C22 121.80(17) . . ?
C21 C22 C17 120.60(16) . . ?
N C23 C24 111.21(13) . . ?
C25 C24 C23 119.83(16) . . ?
C25 C24 C29 119.17(16) . . ?
C29 C24 C23 120.98(16) . . ?
C24 C25 C26 120.62(17) . . ?
C27 C26 C25 119.81(17) . . ?
C26 C27 C28 120.06(17) . . ?
C27 C28 C29 120.13(17) . . ?
C28 C29 C24 120.17(16) . . ?
O1 B N 108.72(13) . . ?
O1 B C11 105.44(13) . . ?
O1 B C17 112.93(14) . . ?
N B C11 108.09(13) . . ?
N B C17 109.60(13) . . ?
C17 B C11 111.85(14) . . ?
C1' O1' B' 121.90(13) . . ?
C23' N' B' 115.39(12) . . ?
O1' C1' C2' 112.73(14) . . ?
O2' C1' O1' 122.88(15) . . ?
O2' C1' C2' 124.35(15) . . ?
C1' C2' C3' 109.89(14) . . ?
C2' C3' C4' 113.58(14) . . ?
C5' C4' C3' 109.93(14) . . ?
C6' C5' C4' 120.62(16) . . ?
C10' C5' C4' 120.78(16) . . ?
C10' C5' C6' 118.37(17) . . ?
C7' C6' C5' 120.92(17) . . ?
C6' C7' C8' 120.02(18) . . ?
C9' C8' C7' 119.59(18) . . ?
C8' C9' C10' 120.25(18) . . ?
C9' C10' C5' 120.83(18) . . ?
C12' C11' C16' 117.30(15) . . ?
C12' C11' B' 125.38(15) . . ?
C16' C11' B' 117.30(14) . . ?
C13' C12' C11' 120.64(16) . . ?
F1' C13' C12' 120.28(16) . . ?
F1' C13' C14' 118.08(16) . . ?
C14' C13' C12' 121.63(16) . . ?
F2' C14' C13' 121.17(16) . . ?
F2' C14' C15' 120.70(16) . . ?
C13' C14' C15' 118.13(16) . . ?
F3' C15' C14' 118.08(16) . . ?
F3' C15' C16' 120.54(16) . . ?
C16' C15' C14' 121.38(16) . . ?
C15' C16' C11' 120.90(16) . . ?
C18' C17' C22' 118.19(16) . . ?
C18' C17' B' 120.91(15) . . ?
C22' C17' B' 120.89(15) . . ?
C19' C18' C17' 120.56(17) . . ?
F4' C19' C18' 120.35(18) . . ?
F4' C19' C20' 118.49(16) . . ?
C20' C19' C18' 121.13(17) . . ?
F5' C20' C19' 120.73(18) . . ?
F5' C20' C21' 120.66(17) . . ?
C21' C20' C19' 118.58(16) . . ?
F6' C21' C20' 117.94(16) . . ?
F6' C21' C22' 120.55(18) . . ?
C20' C21' C22' 121.46(17) . . ?
C21' C22' C17' 120.07(17) . . ?
C24' C23' N' 111.87(13) . . ?
C25' C24' C23' 120.55(16) . . ?
C25' C24' C29' 119.15(16) . . ?
C29' C24' C23' 120.29(16) . . ?
C24' C25' C26' 120.36(16) . . ?
C27' C26' C25' 120.02(17) . . ?
C28' C27' C26' 120.15(17) . . ?
C27' C28' C29' 119.60(17) . . ?
C28' C29' C24' 120.68(16) . . ?
O1' B' N' 109.01(13) . . ?
O1' B' C11' 110.56(13) . . ?
O1' B' C17' 105.71(13) . . ?
N' B' C17' 108.86(13) . . ?
C11' B' N' 110.06(13) . . ?
C11' B' C17' 112.51(13) . . ?
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
N HA O2' 0.91(2) 1.94(2) 2.8484(19) 173.8(19) .
N' HB' O2 0.87(2) 2.25(2) 3.0961(19) 165.6(19) .
_shelx_SHELXL_version_number 2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
14srv256.res created by SHELXL-2014/7
TITL 14srv256 in P-1 #2
REM reset to P-1 #2
REM OMIT -3 132
CELL 1.54184 10.014 11.7859 23.0748 103.8183 98.0649 96.9376
ZERR 4 0.0003 0.0004 0.0007 0.0008 0.001 0.0009
LATT 1
SFAC C H B N O F
UNIT 116 96 4 4 8 24
L.S. 7
PLAN 7
SIZE 0.145 0.207 0.226
TEMP -153.15
HTAB N O2'
HTAB N' O2
FREE HA O2'
FREE O2 HB'
BOND
fmap 2 53
acta 132
OMIT -3 132
OMIT -9 0 14
OMIT 3 5 15
OMIT -9 4 10
OMIT 4 4 15
OMIT -10 0 12
OMIT -10 4 9
OMIT 3 3 18
REM
REM
REM
WGHT 0.107000 0.470000
FVAR 0.32897
F1 6 0.244804 0.488228 0.505973 11.00000 0.11078 0.05698 =
0.06223 0.03086 0.04008 0.00840
F2 6 0.136282 0.660363 0.572759 11.00000 0.05341 0.09344 =
0.04359 0.02083 0.02185 0.00268
F3 6 0.161383 0.876925 0.551688 11.00000 0.05906 0.07910 =
0.05304 0.00409 0.02436 0.02855
F4 6 0.888293 0.795269 0.491347 11.00000 0.04163 0.07763 =
0.04347 0.00613 -0.00830 0.00396
F5 6 0.947159 0.606827 0.411574 11.00000 0.03207 0.06664 =
0.05700 0.02429 0.00378 0.01264
F6 6 0.753374 0.481178 0.316701 11.00000 0.03739 0.04063 =
0.05701 0.01179 0.01406 0.01077
O1 5 0.425241 0.879201 0.387584 11.00000 0.03827 0.02966 =
0.03585 0.00902 0.00672 0.00426
O2 5 0.519164 0.887204 0.305810 11.00000 0.04790 0.03409 =
0.03750 0.00974 0.01127 0.00730
N 4 0.321941 0.679308 0.317199 11.00000 0.03053 0.02934 =
0.03133 0.00873 0.00584 0.00615
HA 2 0.369318 0.672260 0.286035 11.00000 0.03888
HB 2 0.299995 0.606222 0.317834 11.00000 0.02800
C1 1 0.477925 0.935744 0.350879 11.00000 0.03001 0.03375 =
0.03168 0.00868 0.00192 0.00355
C2 1 0.475873 1.066553 0.371768 11.00000 0.03580 0.03307 =
0.03487 0.00727 0.00567 0.00463
AFIX 23
H2A 2 0.524685 1.095945 0.414193 11.00000 -1.20000
H2B 2 0.379832 1.079143 0.371459 11.00000 -1.20000
AFIX 0
C3 1 0.540080 1.139844 0.333776 11.00000 0.03847 0.03350 =
0.04504 0.01301 0.00979 0.00584
AFIX 23
H3A 2 0.495527 1.107978 0.290823 11.00000 -1.20000
H3B 2 0.638095 1.132648 0.336408 11.00000 -1.20000
AFIX 0
C4 1 0.526440 1.271407 0.354619 11.00000 0.03903 0.03300 =
0.04946 0.01155 0.00495 0.00242
AFIX 23
H4A 2 0.562330 1.300669 0.398638 11.00000 -1.20000
H4B 2 0.583531 1.316915 0.333527 11.00000 -1.20000
AFIX 0
C5 1 0.381977 1.294585 0.342665 11.00000 0.04035 0.02453 =
0.04470 0.00797 0.00373 0.00298
C6 1 0.297915 1.299068 0.386211 11.00000 0.04837 0.03168 =
0.04515 0.00962 0.00651 0.00485
AFIX 43
H6 2 0.333027 1.289584 0.424908 11.00000 -1.20000
AFIX 0
C7 1 0.163586 1.317204 0.373797 11.00000 0.04497 0.03931 =
0.06920 0.01549 0.01783 0.00899
AFIX 43
H7 2 0.107395 1.319259 0.403840 11.00000 -1.20000
AFIX 0
C8 1 0.111245 1.332280 0.317935 11.00000 0.04092 0.04096 =
0.08182 0.01848 0.00062 0.00794
AFIX 43
H8 2 0.019448 1.345052 0.309562 11.00000 -1.20000
AFIX 0
C9 1 0.193524 1.328640 0.274250 11.00000 0.05246 0.05029 =
0.05666 0.01818 -0.00331 0.01220
AFIX 43
H9 2 0.158223 1.339041 0.235777 11.00000 -1.20000
AFIX 0
C10 1 0.326985 1.309883 0.286590 11.00000 0.05182 0.03920 =
0.04674 0.01380 0.00875 0.00936
AFIX 43
H10 2 0.382415 1.307358 0.256241 11.00000 -1.20000
AFIX 0
C11 1 0.334765 0.725061 0.434915 11.00000 0.03106 0.03724 =
0.02881 0.00581 0.00177 0.00330
C12 1 0.322797 0.614413 0.447269 11.00000 0.05096 0.03855 =
0.03528 0.00997 0.01229 0.00575
AFIX 43
H12 2 0.361845 0.552842 0.424347 11.00000 -1.20000
AFIX 0
C13 1 0.254320 0.593989 0.492748 11.00000 0.05513 0.04648 =
0.03879 0.01533 0.00980 0.00079
C14 1 0.198052 0.681089 0.527365 11.00000 0.03677 0.06620 =
0.03103 0.01443 0.00848 0.00074
C15 1 0.211388 0.790074 0.515916 11.00000 0.03380 0.06121 =
0.03599 0.00302 0.00616 0.01276
C16 1 0.277138 0.812701 0.470095 11.00000 0.03541 0.04259 =
0.03716 0.00735 0.00461 0.00872
AFIX 43
H16 2 0.283018 0.888795 0.462567 11.00000 -1.20000
AFIX 0
C17 1 0.562580 0.706361 0.386795 11.00000 0.03261 0.03240 =
0.03166 0.01293 0.00515 0.00227
C18 1 0.664596 0.768982 0.435952 11.00000 0.03910 0.04134 =
0.03392 0.01000 0.00471 0.00368
AFIX 43
H18 2 0.646286 0.836016 0.464079 11.00000 -1.20000
AFIX 0
C19 1 0.790737 0.734484 0.443897 11.00000 0.03493 0.05172 =
0.03385 0.01445 -0.00213 0.00042
C20 1 0.822698 0.638433 0.403810 11.00000 0.03012 0.04869 =
0.04558 0.02481 0.00687 0.00751
C21 1 0.722803 0.575758 0.355985 11.00000 0.03545 0.03388 =
0.04158 0.01526 0.01036 0.00564
C22 1 0.594776 0.607812 0.346933 11.00000 0.03193 0.03235 =
0.03624 0.01369 0.00604 0.00224
AFIX 43
H22 2 0.527984 0.562602 0.313370 11.00000 -1.20000
AFIX 0
C23 1 0.192746 0.726096 0.300342 11.00000 0.03558 0.03541 =
0.03768 0.00537 0.00147 0.01062
AFIX 23
H23A 2 0.216210 0.805314 0.293478 11.00000 -1.20000
H23B 2 0.140887 0.734733 0.334228 11.00000 -1.20000
AFIX 0
C24 1 0.104855 0.644437 0.243922 11.00000 0.02962 0.03192 =
0.03749 0.00809 0.00582 0.01176
C25 1 0.007257 0.554691 0.248728 11.00000 0.03202 0.04220 =
0.04030 0.01573 0.00774 0.01068
AFIX 43
H25 2 -0.007380 0.548022 0.287658 11.00000 -1.20000
AFIX 0
C26 1 -0.069262 0.474500 0.197186 11.00000 0.03354 0.03853 =
0.05257 0.01473 0.00331 0.00222
AFIX 43
H26 2 -0.134450 0.412185 0.200880 11.00000 -1.20000
AFIX 0
C27 1 -0.050324 0.485586 0.140454 11.00000 0.03872 0.03635 =
0.04247 0.00274 -0.00176 0.00635
AFIX 43
H27 2 -0.102452 0.430744 0.105115 11.00000 -1.20000
AFIX 0
C28 1 0.044568 0.576567 0.135107 11.00000 0.04219 0.04280 =
0.03423 0.00829 0.00846 0.01165
AFIX 43
H28 2 0.056360 0.584819 0.096098 11.00000 -1.20000
AFIX 0
C29 1 0.122400 0.655638 0.186578 11.00000 0.03219 0.03482 =
0.04100 0.01113 0.00792 0.00583
AFIX 43
H29 2 0.187857 0.717612 0.182743 11.00000 -1.20000
AFIX 0
B 3 0.415264 0.749677 0.381664 11.00000 0.03586 0.02970 =
0.03188 0.00808 0.00487 0.00388
F1' 6 0.251381 1.050408 0.182451 11.00000 0.04494 0.04175 =
0.06195 0.00321 0.01051 0.01747
F2' 6 0.058218 0.930088 0.086069 11.00000 0.03372 0.06070 =
0.05742 0.02064 0.00721 0.01877
F3' 6 0.105297 0.729833 0.011466 11.00000 0.03616 0.06910 =
0.04263 0.00609 -0.00464 0.00932
F4' 6 0.842988 0.573612 -0.021383 11.00000 0.04979 0.06093 =
0.04882 0.00252 0.01867 0.01860
F5' 6 0.862032 0.767103 -0.065640 11.00000 0.04392 0.08094 =
0.03852 0.01404 0.01570 -0.00047
F6' 6 0.745322 0.953445 -0.017132 11.00000 0.06650 0.05512 =
0.05151 0.02653 0.01689 -0.00232
O1' 5 0.531633 0.621227 0.126752 11.00000 0.03480 0.02972 =
0.03172 0.00854 0.00723 0.00635
O2' 5 0.451886 0.650558 0.213616 11.00000 0.04152 0.04001 =
0.03472 0.00843 0.01142 0.00565
N' 4 0.658021 0.819287 0.193445 11.00000 0.02990 0.02910 =
0.03268 0.00811 0.00499 0.00608
HA' 2 0.688379 0.894468 0.193814 11.00000 0.03151
HB' 2 0.610469 0.825559 0.222456 11.00000 0.04264
C1' 1 0.467827 0.584392 0.166906 11.00000 0.02809 0.03493 =
0.03549 0.01286 0.00399 0.00681
C2' 1 0.423292 0.452545 0.149467 11.00000 0.03172 0.03619 =
0.04235 0.01235 0.00492 0.00475
AFIX 23
H2A' 2 0.376584 0.426086 0.106649 11.00000 -1.20000
H2B' 2 0.357934 0.431352 0.175094 11.00000 -1.20000
AFIX 0
C3' 1 0.547624 0.390423 0.157736 11.00000 0.03237 0.03519 =
0.03879 0.00919 0.00310 0.00487
AFIX 23
H3A' 2 0.586488 0.409777 0.201465 11.00000 -1.20000
H3B' 2 0.618133 0.421644 0.136965 11.00000 -1.20000
AFIX 0
C4' 1 0.514944 0.255676 0.133043 11.00000 0.03436 0.03383 =
0.04604 0.00882 0.00379 0.00500
AFIX 23
H4A' 2 0.444683 0.223255 0.153560 11.00000 -1.20000
H4B' 2 0.478027 0.235061 0.089081 11.00000 -1.20000
AFIX 0
C5' 1 0.642546 0.202006 0.143674 11.00000 0.03530 0.02655 =
0.04347 0.00797 0.00604 0.00253
C6' 1 0.684978 0.178866 0.199200 11.00000 0.04239 0.03456 =
0.04530 0.01322 0.01231 0.00794
AFIX 43
H6' 2 0.628219 0.189518 0.229151 11.00000 -1.20000
AFIX 0
C7' 1 0.808882 0.140506 0.211384 11.00000 0.04769 0.04165 =
0.04818 0.01590 0.00394 0.01099
AFIX 43
H7' 2 0.836373 0.124828 0.249427 11.00000 -1.20000
AFIX 0
C8' 1 0.892834 0.124986 0.168004 11.00000 0.03729 0.03875 =
0.06246 0.01392 0.00716 0.01022
AFIX 43
H8' 2 0.978505 0.099996 0.176483 11.00000 -1.20000
AFIX 0
C9' 1 0.851009 0.146107 0.112447 11.00000 0.04253 0.03795 =
0.05619 0.01031 0.01753 0.00574
AFIX 43
H9' 2 0.907584 0.134610 0.082441 11.00000 -1.20000
AFIX 0
C10' 1 0.726682 0.184050 0.100293 11.00000 0.04390 0.03441 =
0.04091 0.01049 0.00845 0.00423
AFIX 43
H10' 2 0.698662 0.197943 0.061864 11.00000 -1.20000
AFIX 0
C11' 1 0.424694 0.805467 0.120439 11.00000 0.03137 0.03233 =
0.03131 0.01268 0.00742 0.00426
C12' 1 0.398253 0.909190 0.157961 11.00000 0.03072 0.03317 =
0.03662 0.00901 0.00495 0.00491
AFIX 43
H12' 2 0.464708 0.952111 0.192174 11.00000 -1.20000
AFIX 0
C13' 1 0.276347 0.949990 0.145799 11.00000 0.03823 0.03284 =
0.04341 0.01110 0.01277 0.00920
C14' 1 0.177102 0.890358 0.097122 11.00000 0.02863 0.04660 =
0.04436 0.02114 0.00982 0.01165
C15' 1 0.202661 0.788017 0.059553 11.00000 0.03141 0.04644 =
0.03233 0.01237 0.00151 0.00221
C16' 1 0.323256 0.745799 0.070507 11.00000 0.03332 0.03722 =
0.03386 0.00893 0.00659 0.00635
AFIX 43
H16' 2 0.338075 0.675230 0.043883 11.00000 -1.20000
AFIX 0
C17' 1 0.650763 0.756381 0.075551 11.00000 0.02848 0.03536 =
0.03005 0.00858 0.00196 0.00297
C18' 1 0.713616 0.661764 0.050382 11.00000 0.03420 0.04015 =
0.03347 0.00938 0.00437 0.00603
AFIX 43
H18' 2 0.706899 0.593148 0.065266 11.00000 -1.20000
AFIX 0
C19' 1 0.785528 0.666839 0.004032 11.00000 0.03386 0.05016 =
0.03466 0.00240 0.00658 0.00867
C20' 1 0.796964 0.765020 -0.018640 11.00000 0.03085 0.06030 =
0.03092 0.00951 0.00703 -0.00141
C21' 1 0.736414 0.859376 0.006526 11.00000 0.03821 0.04652 =
0.03637 0.01590 0.00436 -0.00387
C22' 1 0.663874 0.856595 0.052906 11.00000 0.03423 0.03854 =
0.03537 0.00961 0.00534 0.00195
AFIX 43
H22' 2 0.622774 0.922716 0.069503 11.00000 -1.20000
AFIX 0
C23' 1 0.781028 0.765190 0.211191 11.00000 0.03592 0.03382 =
0.03783 0.00504 0.00075 0.01068
AFIX 23
H1 2 0.751004 0.692397 0.223292 11.00000 -1.20000
H2 2 0.826762 0.742552 0.175750 11.00000 -1.20000
AFIX 0
C24' 1 0.881172 0.849085 0.262645 11.00000 0.03179 0.02965 =
0.03704 0.00834 0.00335 0.01147
C25' 1 0.866005 0.856920 0.322270 11.00000 0.03497 0.03378 =
0.04007 0.01030 0.00824 0.00684
AFIX 43
H25' 2 0.792286 0.808325 0.330715 11.00000 -1.20000
AFIX 0
C26' 1 0.958004 0.935413 0.369658 11.00000 0.04630 0.03791 =
0.03416 0.00760 0.00780 0.00945
AFIX 43
H26' 2 0.948449 0.938981 0.410410 11.00000 -1.20000
AFIX 0
C27' 1 1.063818 1.008590 0.357515 11.00000 0.03981 0.03338 =
0.04138 0.00469 -0.00013 0.00543
AFIX 43
H27' 2 1.125914 1.063016 0.389971 11.00000 -1.20000
AFIX 0
C28' 1 1.079191 1.002505 0.298131 11.00000 0.03438 0.03648 =
0.04775 0.01295 0.00720 0.00561
AFIX 43
H28' 2 1.150876 1.053385 0.289759 11.00000 -1.20000
AFIX 0
C29' 1 0.989202 0.921615 0.250972 11.00000 0.03534 0.03791 =
0.03692 0.01218 0.00710 0.01182
AFIX 43
H29' 2 1.001387 0.915638 0.210317 11.00000 -1.20000
AFIX 0
B' 3 0.563485 0.750145 0.129028 11.00000 0.03155 0.02917 =
0.03114 0.00824 0.00416 0.00443
HKLF 4
REM 14srv256 in P-1 #2
REM R1 = 0.0579 for 7740 Fo > 4sig(Fo) and 0.0608 for all 8496 data
REM 719 parameters refined using 0 restraints
END
WGHT 0.1091 0.4733
REM Highest difference peak 0.388, deepest hole -0.259, 1-sigma level 0.074
Q1 1 0.1626 0.9249 0.5166 11.00000 0.05 0.39
Q2 1 0.4874 0.7809 0.1200 11.00000 0.05 0.38
Q3 1 0.3800 0.7356 0.4159 11.00000 0.05 0.37
Q4 1 0.3495 0.7262 0.4215 11.00000 0.05 0.35
Q5 1 0.4819 1.0948 0.3442 11.00000 0.05 0.33
Q6 1 -0.0598 0.4990 0.1766 11.00000 0.05 0.32
Q7 1 0.1304 0.7484 0.5602 11.00000 0.05 0.32
;
#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Et2O'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_7a_14srv091
_database_code_depnum_ccdc_archive 'CCDC 1563948'
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2017-07-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic 3,4,5-trifluorophenylboroxine
_chemical_formula_moiety 'C18 H6 B3 F9 O3'
_chemical_formula_sum 'C18 H6 B3 F9 O3'
_chemical_formula_weight 473.66
_chemical_melting_point ?
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'
F F 0.0171 0.0103 '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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 12.8358(9)
_cell_length_b 12.6583(9)
_cell_length_c 12.8851(9)
_cell_angle_alpha 90
_cell_angle_beta 119.060(2)
_cell_angle_gamma 90
_cell_volume 1830.0(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3694
_cell_measurement_temperature 293
_cell_measurement_theta_max 29.94
_cell_measurement_theta_min 2.43
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.173
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_correction_T_min 0.6833
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1260 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9160.
The \l/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.719
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 936
_exptl_crystal_size_max 0.541
_exptl_crystal_size_mid 0.226
_exptl_crystal_size_min 0.167
_exptl_special_details
;
The data collection nominally covered full sphere of reciprocal
space, by a combination of 3 runs of narrow-frame \w-scans (scan
width 0.5\% \w, 5s exposure), every run at a different \f angle.
Crystal to detector distance 3.50 cm.
Phase transition on cooling below 210 K.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0292
_diffrn_reflns_av_unetI/netI 0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 9411
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 24.998
_diffrn_reflns_theta_max 24.998
_diffrn_reflns_theta_min 2.426
_diffrn_ambient_temperature 293
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method \w-scan
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1161
_reflns_number_total 1619
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.183
_refine_diff_density_min -0.133
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.078
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 152
_refine_ls_number_reflns 1619
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0594
_refine_ls_R_factor_gt 0.0409
_refine_ls_restrained_S_all 1.078
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.4114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1042
_refine_ls_wR_factor_ref 0.1160
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
C3(H3), C6(H6), C10(H10)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 1.24681(13) 0.250000 0.0993(6) Uani 1 2 d S T P . .
F2 F 0.44405(14) 1.14143(10) 0.39628(13) 0.1033(5) Uani 1 1 d . . . . .
F3 F 0.26001(12) 0.62720(11) 0.55836(12) 0.0989(5) Uani 1 1 d . . . . .
F4 F 0.23598(10) 0.41788(11) 0.53833(11) 0.0891(5) Uani 1 1 d . . . . .
F5 F 0.30333(12) 0.31099(10) 0.40217(13) 0.0999(5) Uani 1 1 d . . . . .
O1 O 0.45189(10) 0.74477(10) 0.30832(10) 0.0607(4) Uani 1 1 d . . . . .
O2 O 0.500000 0.58253(13) 0.250000 0.0563(5) Uani 1 2 d S T P . .
C1 C 0.500000 1.1409(2) 0.250000 0.0659(7) Uani 1 2 d S T P . .
C2 C 0.47049(17) 1.08586(16) 0.32337(17) 0.0650(5) Uani 1 1 d . . . . .
C3 C 0.46848(15) 0.97819(15) 0.32341(15) 0.0603(5) Uani 1 1 d . . . . .
H3 H 0.445578 0.941606 0.373535 0.072 Uiso 1 1 calc R . . . .
C4 C 0.500000 0.9218(2) 0.250000 0.0538(6) Uani 1 2 d S T P . .
C5 C 0.38497(14) 0.57619(14) 0.36370(15) 0.0521(5) Uani 1 1 d . . . . .
C6 C 0.34678(16) 0.63052(15) 0.43310(16) 0.0609(5) Uani 1 1 d . . . . .
H6 H 0.355333 0.705098 0.440787 0.073 Uiso 1 1 calc R . . . .
C7 C 0.29705(16) 0.57683(17) 0.49015(17) 0.0638(5) Uani 1 1 d . . . . .
C8 C 0.28307(14) 0.46991(17) 0.48043(16) 0.0631(5) Uani 1 1 d . . . . .
C9 C 0.31879(16) 0.41619(15) 0.41081(18) 0.0635(5) Uani 1 1 d . . . . .
C10 C 0.36981(15) 0.46756(15) 0.35300(15) 0.0586(5) Uani 1 1 d . . . . .
H10 H 0.394707 0.428801 0.305748 0.070 Uiso 1 1 calc R . . . .
B1 B 0.500000 0.7998(2) 0.250000 0.0551(7) Uani 1 2 d S T P . .
B2 B 0.44702(17) 0.63658(17) 0.30458(17) 0.0536(5) 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 0.1337(16) 0.0617(11) 0.1342(17) 0.000 0.0900(14) 0.000
F2 0.1532(13) 0.0833(9) 0.1261(11) -0.0159(8) 0.1093(10) 0.0029(8)
F3 0.1231(11) 0.1148(11) 0.1097(10) -0.0021(8) 0.0966(9) 0.0104(8)
F4 0.0771(8) 0.1166(11) 0.0957(9) 0.0297(7) 0.0595(7) -0.0034(7)
F5 0.1142(10) 0.0684(9) 0.1380(12) 0.0039(7) 0.0778(9) -0.0111(7)
O1 0.0700(8) 0.0659(8) 0.0655(8) -0.0018(6) 0.0480(7) -0.0012(6)
O2 0.0595(10) 0.0644(11) 0.0620(10) 0.000 0.0428(9) 0.000
C1 0.0701(17) 0.0585(17) 0.0778(19) 0.000 0.0429(15) 0.000
C2 0.0712(12) 0.0711(13) 0.0710(13) -0.0085(10) 0.0488(11) 0.0016(9)
C3 0.0630(11) 0.0695(13) 0.0614(11) 0.0011(9) 0.0405(10) -0.0006(9)
C4 0.0484(13) 0.0683(16) 0.0496(14) 0.000 0.0277(11) 0.000
C5 0.0462(9) 0.0650(12) 0.0502(10) 0.0001(8) 0.0275(8) 0.0019(8)
C6 0.0635(11) 0.0662(11) 0.0668(12) 0.0016(9) 0.0424(10) 0.0032(9)
C7 0.0626(11) 0.0824(14) 0.0650(12) 0.0024(10) 0.0455(10) 0.0068(9)
C8 0.0467(10) 0.0881(15) 0.0622(11) 0.0161(10) 0.0325(9) 0.0019(9)
C9 0.0556(10) 0.0625(12) 0.0746(13) 0.0059(9) 0.0333(10) -0.0029(9)
C10 0.0525(10) 0.0702(12) 0.0603(11) -0.0006(9) 0.0331(9) 0.0033(8)
B1 0.0516(15) 0.0690(19) 0.0505(16) 0.000 0.0293(13) 0.000
B2 0.0482(11) 0.0674(14) 0.0492(11) 0.0004(9) 0.0268(9) 0.0017(9)
_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 C1 1.341(3) . ?
F2 C2 1.343(2) . ?
F3 C7 1.346(2) . ?
F4 C8 1.339(2) . ?
F5 C9 1.343(2) . ?
O1 B1 1.372(2) . ?
O1 B2 1.371(2) . ?
O2 B2 1.375(2) . ?
O2 B2 1.375(2) 2_655 ?
C1 C2 1.368(2) . ?
C1 C2 1.368(2) 2_655 ?
C2 C3 1.363(3) . ?
C3 C4 1.393(2) . ?
C4 B1 1.544(4) . ?
C5 C6 1.392(2) . ?
C5 C10 1.386(2) . ?
C5 B2 1.545(3) . ?
C6 C7 1.366(2) . ?
C7 C8 1.363(3) . ?
C8 C9 1.370(3) . ?
C9 C10 1.371(3) . ?
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
B2 O1 B1 120.87(16) . . ?
B2 O2 B2 120.3(2) 2_655 . ?
F1 C1 C2 120.62(13) . . ?
F1 C1 C2 120.62(13) . 2_655 ?
C2 C1 C2 118.8(3) . 2_655 ?
F2 C2 C1 117.77(19) . . ?
F2 C2 C3 120.82(17) . . ?
C3 C2 C1 121.41(18) . . ?
C2 C3 C4 120.03(18) . . ?
C3 C4 C3 118.3(2) 2_655 . ?
C3 C4 B1 120.83(12) 2_655 . ?
C3 C4 B1 120.83(12) . . ?
C6 C5 B2 119.92(17) . . ?
C10 C5 C6 118.53(17) . . ?
C10 C5 B2 121.51(16) . . ?
C7 C6 C5 120.15(18) . . ?
F3 C7 C6 121.44(19) . . ?
F3 C7 C8 117.25(17) . . ?
C8 C7 C6 121.31(18) . . ?
F4 C8 C7 120.80(19) . . ?
F4 C8 C9 120.38(19) . . ?
C7 C8 C9 118.82(17) . . ?
F5 C9 C8 117.62(17) . . ?
F5 C9 C10 121.03(18) . . ?
C8 C9 C10 121.35(18) . . ?
C9 C10 C5 119.82(17) . . ?
O1 B1 O1 119.0(2) . 2_655 ?
O1 B1 C4 120.52(12) 2_655 . ?
O1 B1 C4 120.52(12) . . ?
O1 B2 O2 119.33(17) . . ?
O1 B2 C5 120.17(16) . . ?
O2 B2 C5 120.49(18) . . ?
_shelx_res_file
;
TITL 14asb002 in C2/c
14srv091.res
created by SHELXL-2016/6 at 03:18:23 on 23-Jul-2017
CELL 0.71073 12.8358 12.6583 12.8851 90 119.0604 90
ZERR 4 0.0009 0.0009 0.0009 0 0.0022 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H B F O
UNIT 72 24 12 36 12
L.S. 7 0 0
PLAN 6
TEMP -153.15
fmap 2 53
acta 50
OMIT -3 50
REM
REM
REM
WGHT 0.060700 0.411400
FVAR 0.42998
F1 4 0.500000 1.246806 0.250000 10.50000 0.13369 0.06174 =
0.13423 0.00000 0.09000 0.00000
F2 4 0.444054 1.141427 0.396283 11.00000 0.15316 0.08332 =
0.12608 -0.01594 0.10929 0.00287
F3 4 0.260008 0.627195 0.558356 11.00000 0.12310 0.11476 =
0.10973 -0.00213 0.09657 0.01038
F4 4 0.235980 0.417877 0.538331 11.00000 0.07708 0.11663 =
0.09573 0.02969 0.05946 -0.00338
F5 4 0.303330 0.310995 0.402166 11.00000 0.11420 0.06838 =
0.13797 0.00393 0.07776 -0.01106
O1 5 0.451890 0.744772 0.308320 11.00000 0.07003 0.06588 =
0.06553 -0.00177 0.04804 -0.00123
O2 5 0.500000 0.582526 0.250000 10.50000 0.05951 0.06439 =
0.06196 0.00000 0.04278 0.00000
C1 1 0.500000 1.140880 0.250000 10.50000 0.07010 0.05853 =
0.07782 0.00000 0.04286 0.00000
C2 1 0.470488 1.085858 0.323366 11.00000 0.07121 0.07106 =
0.07098 -0.00846 0.04883 0.00162
C3 1 0.468483 0.978190 0.323410 11.00000 0.06301 0.06946 =
0.06145 0.00112 0.04055 -0.00059
AFIX 43
H3 2 0.445578 0.941606 0.373535 11.00000 -1.20000
AFIX 0
C4 1 0.500000 0.921799 0.250000 10.50000 0.04845 0.06827 =
0.04955 0.00000 0.02774 0.00000
C5 1 0.384970 0.576188 0.363702 11.00000 0.04620 0.06498 =
0.05016 0.00013 0.02749 0.00194
C6 1 0.346781 0.630520 0.433102 11.00000 0.06347 0.06617 =
0.06676 0.00158 0.04241 0.00324
AFIX 43
H6 2 0.355333 0.705098 0.440787 11.00000 -1.20000
AFIX 0
C7 1 0.297054 0.576834 0.490155 11.00000 0.06256 0.08238 =
0.06497 0.00236 0.04553 0.00678
C8 1 0.283069 0.469911 0.480431 11.00000 0.04669 0.08808 =
0.06223 0.01611 0.03253 0.00188
C9 1 0.318789 0.416188 0.410812 11.00000 0.05564 0.06250 =
0.07462 0.00594 0.03333 -0.00288
C10 1 0.369814 0.467557 0.353002 11.00000 0.05254 0.07017 =
0.06034 -0.00062 0.03313 0.00333
AFIX 43
H10 2 0.394707 0.428801 0.305748 11.00000 -1.20000
AFIX 0
B1 3 0.500000 0.799815 0.250000 10.50000 0.05156 0.06900 =
0.05053 0.00000 0.02933 0.00000
B2 3 0.447019 0.636578 0.304579 11.00000 0.04823 0.06743 =
0.04923 0.00038 0.02684 0.00173
HKLF 4
REM 14asb002 in C2/c
REM R1 = 0.0409 for 1161 Fo > 4sig(Fo) and 0.0594 for all 1619 data
REM 152 parameters refined using 0 restraints
END
WGHT 0.0607 0.4115
REM Highest difference peak 0.183, deepest hole -0.133, 1-sigma level 0.045
Q1 1 0.4459 1.0255 0.2966 11.00000 0.05 0.18
Q2 1 0.3167 0.6672 0.4048 11.00000 0.05 0.18
Q3 1 0.3382 0.5211 0.3195 11.00000 0.05 0.17
Q4 1 0.2543 0.5240 0.4476 11.00000 0.05 0.16
Q5 1 0.3142 0.5119 0.5069 11.00000 0.05 0.15
Q6 1 0.5021 0.9403 0.3008 11.00000 0.05 0.15
;
_shelx_res_checksum 15981
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_11d_16srv431
_database_code_depnum_ccdc_archive 'CCDC 1551624'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2016-11-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common ?
_chemical_name_systematic
'Di-2-iodophenylboronic B-O-B di-2-phenylacetate '
_chemical_formula_moiety 'C28 H22 B2 I2 O5'
_chemical_formula_sum 'C28 H22 B2 I2 O5'
_chemical_formula_weight 713.87
_chemical_melting_point 382(1)
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'
I I -0.4742 1.8119 '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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.6350(5)
_cell_length_b 11.4814(5)
_cell_length_c 12.2457(6)
_cell_angle_alpha 83.1389(18)
_cell_angle_beta 87.0947(19)
_cell_angle_gamma 64.1817(17)
_cell_volume 1336.36(11)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9017
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 31.29
_cell_measurement_theta_min 2.45
_shelx_estimated_absorpt_T_max 0.890
_shelx_estimated_absorpt_T_min 0.621
_exptl_absorpt_coefficient_mu 2.390
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8689
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.8689.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.774
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 692
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0289
_diffrn_reflns_av_unetI/netI 0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 21913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.999
_diffrn_reflns_theta_min 2.453
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6143
_reflns_number_total 7764
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.830
_refine_diff_density_min -0.604
_refine_diff_density_rms 0.104
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 334
_refine_ls_number_reflns 7764
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0448
_refine_ls_R_factor_gt 0.0286
_refine_ls_restrained_S_all 1.036
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0538
_refine_ls_wR_factor_ref 0.0580
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C14(H14A,H14B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.38294(2) 0.66826(2) 0.33947(2) 0.02343(5) Uani 1 1 d . . . . .
I2 I 0.71523(2) 1.27960(2) 0.34759(2) 0.02189(5) Uani 1 1 d . . . . .
O1 O 0.98260(16) 1.05923(14) 0.18677(12) 0.0143(3) Uani 1 1 d . . . . .
O2 O 1.12063(16) 0.83051(14) 0.16755(12) 0.0165(3) Uani 1 1 d . . . . .
O3 O 0.90114(16) 0.92433(15) 0.10352(13) 0.0179(3) Uani 1 1 d . . . . .
O4 O 1.05693(16) 0.90559(15) 0.34945(12) 0.0151(3) Uani 1 1 d . . . . .
O5 O 0.83857(17) 0.96873(15) 0.29183(12) 0.0185(3) Uani 1 1 d . . . . .
C1 C 1.2432(2) 0.9550(2) 0.23752(18) 0.0151(4) Uani 1 1 d . . . . .
C2 C 1.3695(2) 0.8535(2) 0.27539(18) 0.0173(5) Uani 1 1 d . . . . .
C3 C 1.4945(3) 0.8642(2) 0.2709(2) 0.0229(5) Uani 1 1 d . . . . .
H3 H 1.5780 0.7927 0.2980 0.027 Uiso 1 1 calc R . . . .
C4 C 1.4967(3) 0.9796(3) 0.2266(2) 0.0281(6) Uani 1 1 d . . . . .
H4 H 1.5821 0.9875 0.2220 0.034 Uiso 1 1 calc R . . . .
C5 C 1.3742(3) 1.0835(3) 0.1890(2) 0.0264(6) Uani 1 1 d . . . . .
H5 H 1.3751 1.1633 0.1587 0.032 Uiso 1 1 calc R . . . .
C6 C 1.2501(3) 1.0711(2) 0.19551(19) 0.0199(5) Uani 1 1 d . . . . .
H6 H 1.1665 1.1440 0.1706 0.024 Uiso 1 1 calc R . . . .
C7 C 0.7223(2) 1.1531(2) 0.13606(18) 0.0153(4) Uani 1 1 d . . . . .
C8 C 0.6510(2) 1.2635(2) 0.19118(18) 0.0174(5) Uani 1 1 d . . . . .
C9 C 0.5301(3) 1.3681(2) 0.1499(2) 0.0253(5) Uani 1 1 d . . . . .
H9 H 0.4848 1.4419 0.1895 0.030 Uiso 1 1 calc R . . . .
C10 C 0.4761(3) 1.3644(3) 0.0510(2) 0.0270(6) Uani 1 1 d . . . . .
H10 H 0.3937 1.4358 0.0220 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5418(3) 1.2566(2) -0.00576(19) 0.0228(5) Uani 1 1 d . . . . .
H11 H 0.5042 1.2534 -0.0735 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6623(2) 1.1535(2) 0.03621(18) 0.0185(5) Uani 1 1 d . . . . .
H12 H 0.7063 1.0800 -0.0039 0.022 Uiso 1 1 calc R . . . .
C13 C 1.0260(2) 0.8348(2) 0.10628(18) 0.0167(5) Uani 1 1 d . . . . .
C14 C 1.0601(3) 0.7256(2) 0.03764(18) 0.0204(5) Uani 1 1 d . . . . .
H14A H 1.1606 0.6878 0.0185 0.024 Uiso 1 1 calc R . . . .
H14B H 1.0053 0.7582 -0.0314 0.024 Uiso 1 1 calc R . . . .
C15 C 1.0251(2) 0.6225(2) 0.10278(18) 0.0160(4) Uani 1 1 d . . . . .
C16 C 1.1231(3) 0.5272(2) 0.1750(2) 0.0211(5) Uani 1 1 d . . . . .
H16 H 1.2107 0.5283 0.1844 0.025 Uiso 1 1 calc R . . . .
C17 C 1.0940(3) 0.4311(2) 0.2331(2) 0.0294(6) Uani 1 1 d . . . . .
H17 H 1.1619 0.3659 0.2818 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9676(3) 0.4297(3) 0.2208(2) 0.0346(7) Uani 1 1 d . . . . .
H18 H 0.9483 0.3629 0.2601 0.042 Uiso 1 1 calc R . . . .
C19 C 0.8680(3) 0.5254(3) 0.1511(2) 0.0346(7) Uani 1 1 d . . . . .
H19 H 0.7798 0.5249 0.1436 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8965(3) 0.6219(3) 0.0922(2) 0.0264(6) Uani 1 1 d . . . . .
H20 H 0.8277 0.6876 0.0446 0.032 Uiso 1 1 calc R . . . .
C21 C 0.9315(2) 0.9245(2) 0.36636(18) 0.0170(5) Uani 1 1 d . . . . .
C22 C 0.8909(3) 0.8944(2) 0.48128(18) 0.0212(5) Uani 1 1 d . . . . .
H22A H 0.8324 0.9772 0.5120 0.025 Uiso 1 1 calc R . . . .
H22B H 0.9765 0.8486 0.5268 0.025 Uiso 1 1 calc R . . . .
C23 C 0.8117(2) 0.8118(2) 0.48992(18) 0.0180(5) Uani 1 1 d . . . . .
C24 C 0.8688(3) 0.6903(2) 0.4525(2) 0.0281(6) Uani 1 1 d . . . . .
H24 H 0.9569 0.6594 0.4166 0.034 Uiso 1 1 calc R . . . .
C25 C 0.7968(4) 0.6136(3) 0.4675(2) 0.0388(7) Uani 1 1 d . . . . .
H25 H 0.8353 0.5304 0.4413 0.047 Uiso 1 1 calc R . . . .
C26 C 0.6699(3) 0.6580(3) 0.5202(2) 0.0398(8) Uani 1 1 d . . . . .
H26 H 0.6219 0.6045 0.5319 0.048 Uiso 1 1 calc R . . . .
C27 C 0.6124(3) 0.7789(3) 0.5559(2) 0.0364(7) Uani 1 1 d . . . . .
H27 H 0.5241 0.8095 0.5915 0.044 Uiso 1 1 calc R . . . .
C28 C 0.6818(3) 0.8563(3) 0.5405(2) 0.0243(5) Uani 1 1 d . . . . .
H28 H 0.6407 0.9406 0.5646 0.029 Uiso 1 1 calc R . . . .
B1 B 1.0974(3) 0.9481(2) 0.2321(2) 0.0155(5) Uani 1 1 d . . . . .
B2 B 0.8650(3) 1.0351(2) 0.1776(2) 0.0166(5) 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
I1 0.03071(10) 0.01540(8) 0.02123(9) -0.00072(6) -0.00527(7) -0.00701(7)
I2 0.02197(9) 0.02611(9) 0.01929(8) -0.00841(6) 0.00090(6) -0.01059(7)
O1 0.0159(8) 0.0142(7) 0.0140(8) -0.0018(6) 0.0024(6) -0.0078(6)
O2 0.0213(9) 0.0136(7) 0.0162(8) -0.0031(6) 0.0001(6) -0.0088(7)
O3 0.0204(9) 0.0155(8) 0.0179(8) -0.0030(6) -0.0032(6) -0.0074(7)
O4 0.0171(8) 0.0180(8) 0.0113(7) -0.0007(6) -0.0004(6) -0.0087(6)
O5 0.0210(8) 0.0246(8) 0.0139(8) 0.0019(7) -0.0008(6) -0.0145(7)
C1 0.0189(11) 0.0160(10) 0.0123(10) -0.0041(9) 0.0022(8) -0.0089(9)
C2 0.0226(12) 0.0179(11) 0.0113(10) -0.0018(9) 0.0015(9) -0.0087(9)
C3 0.0168(12) 0.0303(13) 0.0193(12) -0.0036(10) 0.0003(9) -0.0079(10)
C4 0.0265(14) 0.0425(16) 0.0240(13) -0.0030(12) 0.0039(11) -0.0237(12)
C5 0.0336(15) 0.0301(14) 0.0240(13) 0.0038(11) -0.0011(11) -0.0231(12)
C6 0.0222(12) 0.0222(12) 0.0176(11) -0.0003(10) -0.0018(9) -0.0120(10)
C7 0.0174(11) 0.0196(11) 0.0124(10) -0.0003(9) 0.0033(8) -0.0120(9)
C8 0.0183(12) 0.0222(12) 0.0131(11) -0.0026(9) 0.0024(9) -0.0102(10)
C9 0.0236(13) 0.0240(13) 0.0229(13) -0.0072(11) 0.0024(10) -0.0044(10)
C10 0.0215(13) 0.0269(13) 0.0236(13) 0.0002(11) -0.0032(10) -0.0024(10)
C11 0.0244(13) 0.0291(13) 0.0130(11) -0.0009(10) 0.0000(9) -0.0101(11)
C12 0.0186(12) 0.0225(12) 0.0135(11) -0.0026(9) 0.0037(9) -0.0084(10)
C13 0.0252(13) 0.0135(10) 0.0137(11) 0.0031(9) 0.0014(9) -0.0117(9)
C14 0.0326(14) 0.0180(11) 0.0128(11) -0.0035(9) 0.0002(10) -0.0126(10)
C15 0.0218(12) 0.0134(10) 0.0141(11) -0.0046(9) 0.0013(9) -0.0084(9)
C16 0.0216(12) 0.0188(11) 0.0228(12) -0.0016(10) -0.0008(10) -0.0087(10)
C17 0.0379(16) 0.0205(13) 0.0246(14) 0.0038(11) -0.0026(12) -0.0090(11)
C18 0.0522(19) 0.0312(15) 0.0310(15) -0.0014(12) 0.0076(13) -0.0291(14)
C19 0.0324(16) 0.0440(17) 0.0395(16) -0.0109(14) 0.0025(13) -0.0264(14)
C20 0.0243(13) 0.0259(13) 0.0300(14) -0.0034(11) -0.0065(11) -0.0111(11)
C21 0.0209(12) 0.0183(11) 0.0154(11) -0.0029(9) 0.0011(9) -0.0117(9)
C22 0.0249(13) 0.0316(13) 0.0121(11) 0.0011(10) 0.0000(9) -0.0177(11)
C23 0.0212(12) 0.0239(12) 0.0100(10) 0.0047(9) -0.0027(9) -0.0120(10)
C24 0.0350(15) 0.0245(13) 0.0221(13) -0.0006(11) 0.0016(11) -0.0111(11)
C25 0.068(2) 0.0238(14) 0.0271(15) 0.0052(12) -0.0140(15) -0.0226(14)
C26 0.053(2) 0.0509(19) 0.0313(16) 0.0190(14) -0.0178(14) -0.0414(17)
C27 0.0284(15) 0.0545(19) 0.0316(15) 0.0123(14) -0.0036(12) -0.0267(14)
C28 0.0219(13) 0.0303(13) 0.0186(12) 0.0041(10) -0.0008(10) -0.0110(11)
B1 0.0198(13) 0.0132(11) 0.0149(12) -0.0039(10) 0.0032(10) -0.0081(10)
B2 0.0211(13) 0.0165(12) 0.0140(12) -0.0010(10) 0.0008(10) -0.0101(10)
_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
I1 C2 2.123(2) . ?
I2 C8 2.121(2) . ?
O1 B1 1.403(3) . ?
O1 B2 1.406(3) . ?
O2 C13 1.266(3) . ?
O2 B1 1.567(3) . ?
O3 C13 1.276(3) . ?
O3 B2 1.549(3) . ?
O4 C21 1.265(3) . ?
O4 B1 1.563(3) . ?
O5 C21 1.269(3) . ?
O5 B2 1.584(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.401(3) . ?
C1 B1 1.591(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.380(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.386(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.406(3) . ?
C7 B2 1.588(3) . ?
C8 C9 1.389(3) . ?
C9 C10 1.380(4) . ?
C10 C11 1.380(3) . ?
C11 C12 1.382(3) . ?
C13 C14 1.496(3) . ?
C14 C15 1.518(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.384(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.368(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.385(4) . ?
C21 C22 1.496(3) . ?
C22 C23 1.511(3) . ?
C23 C24 1.382(3) . ?
C23 C28 1.389(3) . ?
C24 C25 1.389(4) . ?
C25 C26 1.375(5) . ?
C26 C27 1.368(4) . ?
C27 C28 1.374(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
B1 O1 B2 111.77(18) . . ?
C13 O2 B1 121.02(18) . . ?
C13 O3 B2 117.88(18) . . ?
C21 O4 B1 118.15(18) . . ?
C21 O5 B2 120.15(18) . . ?
C2 C1 C6 115.4(2) . . ?
C2 C1 B1 126.3(2) . . ?
C6 C1 B1 118.2(2) . . ?
C1 C2 I1 121.50(16) . . ?
C3 C2 I1 115.38(17) . . ?
C3 C2 C1 123.1(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 C1 122.5(2) . . ?
C8 C7 C12 115.6(2) . . ?
C8 C7 B2 124.0(2) . . ?
C12 C7 B2 120.3(2) . . ?
C7 C8 I2 122.22(17) . . ?
C9 C8 I2 115.08(17) . . ?
C9 C8 C7 122.7(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 C9 119.9(2) . . ?
C10 C11 C12 119.8(2) . . ?
C11 C12 C7 122.4(2) . . ?
O2 C13 O3 123.6(2) . . ?
O2 C13 C14 118.3(2) . . ?
O3 C13 C14 118.0(2) . . ?
C13 C14 C15 108.64(18) . . ?
C16 C15 C14 119.7(2) . . ?
C20 C15 C14 121.1(2) . . ?
C20 C15 C16 119.1(2) . . ?
C17 C16 C15 120.5(2) . . ?
C18 C17 C16 120.1(2) . . ?
C17 C18 C19 120.1(2) . . ?
C18 C19 C20 120.2(3) . . ?
C15 C20 C19 120.0(2) . . ?
O4 C21 O5 123.7(2) . . ?
O4 C21 C22 117.7(2) . . ?
O5 C21 C22 118.6(2) . . ?
C21 C22 C23 113.99(19) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 C28 119.4(2) . . ?
C28 C23 C22 119.4(2) . . ?
C23 C24 C25 119.7(3) . . ?
C26 C25 C24 120.1(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C28 120.2(3) . . ?
C27 C28 C23 120.3(3) . . ?
O1 B1 O2 109.09(18) . . ?
O1 B1 O4 108.61(18) . . ?
O1 B1 C1 118.13(19) . . ?
O2 B1 C1 107.74(17) . . ?
O4 B1 O2 102.55(16) . . ?
O4 B1 C1 109.59(18) . . ?
O1 B2 O3 109.39(18) . . ?
O1 B2 O5 109.15(18) . . ?
O1 B2 C7 118.47(19) . . ?
O3 B2 O5 101.05(16) . . ?
O3 B2 C7 108.68(18) . . ?
O5 B2 C7 108.69(18) . . ?
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
C1 B1 O2 C13 -145.81(19) . . . . ?
C1 B1 O4 C21 163.42(19) . . . . ?
C2 C1 B1 O1 -177.2(2) . . . . ?
C2 C1 B1 O2 -53.1(3) . . . . ?
C2 C1 B1 O4 57.7(3) . . . . ?
C6 C1 B1 O1 -0.8(3) . . . . ?
C6 C1 B1 O2 123.3(2) . . . . ?
C6 C1 B1 O4 -125.9(2) . . . . ?
C7 B2 O3 C13 163.67(18) . . . . ?
C7 B2 O5 C21 -143.4(2) . . . . ?
C8 C7 B2 O1 -61.7(3) . . . . ?
C8 C7 B2 O3 172.74(19) . . . . ?
C8 C7 B2 O5 63.6(3) . . . . ?
C12 C7 B2 O1 115.9(2) . . . . ?
C12 C7 B2 O3 -9.7(3) . . . . ?
C12 C7 B2 O5 -118.9(2) . . . . ?
C13 O2 B1 O1 -16.4(3) . . . . ?
C13 O2 B1 O4 98.6(2) . . . . ?
C13 O3 B2 O1 32.9(3) . . . . ?
C13 O3 B2 O5 -82.1(2) . . . . ?
C13 C14 C15 C16 -86.1(3) . . . . ?
C13 C14 C15 C20 93.5(3) . . . . ?
C15 C14 C13 O2 90.8(2) . . . . ?
C15 C14 C13 O3 -86.1(2) . . . . ?
C21 O4 B1 O1 33.0(3) . . . . ?
C21 O4 B1 O2 -82.3(2) . . . . ?
C21 O5 B2 O1 -12.9(3) . . . . ?
C21 O5 B2 O3 102.3(2) . . . . ?
C21 C22 C23 C24 58.2(3) . . . . ?
C21 C22 C23 C28 -124.5(2) . . . . ?
C23 C22 C21 O4 -130.9(2) . . . . ?
C23 C22 C21 O5 49.9(3) . . . . ?
B1 O1 B2 O3 -59.2(2) . . . . ?
B1 O1 B2 O5 50.5(2) . . . . ?
B1 O1 B2 C7 175.52(19) . . . . ?
B1 O2 C13 O3 -9.8(3) . . . . ?
B1 O2 C13 C14 173.48(18) . . . . ?
B1 O4 C21 O5 4.4(3) . . . . ?
B1 O4 C21 C22 -174.70(19) . . . . ?
B2 O1 B1 O2 50.8(2) . . . . ?
B2 O1 B1 O4 -60.2(2) . . . . ?
B2 O1 B1 C1 174.23(19) . . . . ?
B2 O3 C13 O2 1.4(3) . . . . ?
B2 O3 C13 C14 178.10(18) . . . . ?
B2 O5 C21 O4 -14.7(3) . . . . ?
B2 O5 C21 C22 164.4(2) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
TITL 16srv431
CELL 0.71073 10.635 11.4814 12.2457 83.1389 87.0947 64.1817
ZERR 2 0.0005 0.0005 0.0006 0.0018 0.0019 0.0017
LATT 1
SFAC C H B I O
UNIT 56 44 4 4 10
L.S. 9
PLAN 5
SIZE 0.05 0.15 0.22
TEMP -153.15
CONF C2 C1 B1 O1
CONF C2 C1 B1 O2
CONF C2 C1 B1 O4
CONF C6 C1 B1 O1
CONF C6 C1 B1 O2
CONF C6 C1 B1 O4
CONF B2 O1 B1 O2
CONF B2 O1 B1 O4
CONF B2 O1 B1 C1
CONF C13 O2 B1 O1
CONF C13 O2 B1 O4
CONF C1 B1 O2 C13
CONF C21 O4 B1 O1
CONF C21 O4 B1 O2
CONF C1 B1 O4 C21
CONF B1 O1 B2 O3
CONF B1 O1 B2 O5
CONF B1 O1 B2 C7
CONF B1 O4 C21 O5
CONF B1 O4 C21 C22
CONF B1 O2 C13 O3
CONF B1 O2 C13 C14
CONF B2 O3 C13 O2
CONF B2 O3 C13 C14
CONF C13 O3 B2 O1
CONF C13 O3 B2 O5
CONF C7 B2 O3 C13
CONF C21 O5 B2 O1
CONF C21 O5 B2 O3
CONF C7 B2 O5 C21
CONF B2 O5 C21 O4
CONF B2 O5 C21 C22
CONF C8 C7 B2 O1
CONF C8 C7 B2 O3
CONF C8 C7 B2 O5
CONF C12 C7 B2 O1
CONF C12 C7 B2 O3
CONF C12 C7 B2 O5
CONF C15 C14 C13 O2
CONF C15 C14 C13 O3
CONF C13 C14 C15 C16
CONF C13 C14 C15 C20
CONF C23 C22 C21 O4
CONF C23 C22 C21 O5
CONF C21 C22 C23 C24
CONF C21 C22 C23 C28
fmap 2 53
acta
OMIT -2 60
OMIT 1 0 0
WGHT 0.02 0.9
FVAR 0.15839
REM
REM
REM
I1 4 1.38294 0.66826 0.33947 11.00000 0.03071 0.01540 0.02123 =
-0.00072 -0.00527 -0.00701
I2 4 0.71523 1.27961 0.34759 11.00000 0.02197 0.02611 0.01929 =
-0.00841 0.00090 -0.01059
O1 5 0.98260 1.05923 0.18677 11.00000 0.01585 0.01419 0.01399 =
-0.00179 0.00236 -0.00781
O2 5 1.12063 0.83051 0.16755 11.00000 0.02132 0.01360 0.01623 =
-0.00311 0.00006 -0.00881
O3 5 0.90114 0.92434 0.10352 11.00000 0.02043 0.01551 0.01791 =
-0.00296 -0.00319 -0.00740
O4 5 1.05693 0.90559 0.34945 11.00000 0.01705 0.01802 0.01126 =
-0.00070 -0.00037 -0.00866
O5 5 0.83857 0.96873 0.29183 11.00000 0.02096 0.02458 0.01390 =
0.00192 -0.00078 -0.01454
C1 1 1.24319 0.95503 0.23752 11.00000 0.01894 0.01598 0.01234 =
-0.00406 0.00216 -0.00895
C2 1 1.36949 0.85348 0.27539 11.00000 0.02255 0.01794 0.01131 =
-0.00182 0.00147 -0.00864
C3 1 1.49451 0.86418 0.27085 11.00000 0.01684 0.03030 0.01928 =
-0.00365 0.00027 -0.00793
AFIX 43
H3 2 1.57801 0.79268 0.29797 11.00000 -1.20000
AFIX 0
C4 1 1.49668 0.97957 0.22660 11.00000 0.02653 0.04255 0.02404 =
-0.00295 0.00394 -0.02370
AFIX 43
H4 2 1.58210 0.98750 0.22203 11.00000 -1.20000
AFIX 0
C5 1 1.37425 1.08354 0.18896 11.00000 0.03359 0.03007 0.02400 =
0.00382 -0.00107 -0.02311
AFIX 43
H5 2 1.37515 1.16330 0.15868 11.00000 -1.20000
AFIX 0
C6 1 1.25010 1.07111 0.19551 11.00000 0.02217 0.02221 0.01755 =
-0.00029 -0.00181 -0.01201
AFIX 43
H6 2 1.16652 1.14404 0.17057 11.00000 -1.20000
AFIX 0
C7 1 0.72228 1.15310 0.13606 11.00000 0.01740 0.01958 0.01243 =
-0.00026 0.00329 -0.01204
C8 1 0.65096 1.26345 0.19118 11.00000 0.01831 0.02217 0.01313 =
-0.00264 0.00244 -0.01016
C9 1 0.53006 1.36814 0.14991 11.00000 0.02361 0.02401 0.02293 =
-0.00717 0.00238 -0.00439
AFIX 43
H9 2 0.48483 1.44185 0.18951 11.00000 -1.20000
AFIX 0
C10 1 0.47606 1.36436 0.05097 11.00000 0.02148 0.02687 0.02362 =
0.00022 -0.00322 -0.00241
AFIX 43
H10 2 0.39373 1.43585 0.02195 11.00000 -1.20000
AFIX 0
C11 1 0.54175 1.25662 -0.00576 11.00000 0.02438 0.02907 0.01295 =
-0.00091 -0.00004 -0.01007
AFIX 43
H11 2 0.50421 1.25339 -0.07349 11.00000 -1.20000
AFIX 0
C12 1 0.66231 1.15345 0.03621 11.00000 0.01858 0.02254 0.01355 =
-0.00263 0.00367 -0.00840
AFIX 43
H12 2 0.70631 1.08004 -0.00388 11.00000 -1.20000
AFIX 0
C13 1 1.02600 0.83483 0.10628 11.00000 0.02523 0.01350 0.01370 =
0.00311 0.00144 -0.01172
C14 1 1.06014 0.72556 0.03764 11.00000 0.03260 0.01803 0.01285 =
-0.00353 0.00019 -0.01258
AFIX 23
H14a 2 1.16062 0.68781 0.01848 11.00000 -1.20000
H14b 2 1.00528 0.75820 -0.03143 11.00000 -1.20000
AFIX 0
C15 1 1.02512 0.62246 0.10278 11.00000 0.02182 0.01344 0.01409 =
-0.00456 0.00131 -0.00838
C16 1 1.12315 0.52725 0.17501 11.00000 0.02157 0.01877 0.02282 =
-0.00158 -0.00081 -0.00867
AFIX 43
H16 2 1.21075 0.52831 0.18444 11.00000 -1.20000
AFIX 0
C17 1 1.09402 0.43113 0.23313 11.00000 0.03794 0.02046 0.02456 =
0.00385 -0.00260 -0.00897
AFIX 43
H17 2 1.16189 0.36593 0.28176 11.00000 -1.20000
AFIX 0
C18 1 0.96763 0.42968 0.22078 11.00000 0.05221 0.03122 0.03104 =
-0.00145 0.00765 -0.02915
AFIX 43
H18 2 0.94827 0.36285 0.26013 11.00000 -1.20000
AFIX 0
C19 1 0.86803 0.52538 0.15111 11.00000 0.03243 0.04405 0.03950 =
-0.01087 0.00248 -0.02637
AFIX 43
H19 2 0.77977 0.52494 0.14361 11.00000 -1.20000
AFIX 0
C20 1 0.89646 0.62187 0.09220 11.00000 0.02429 0.02592 0.02996 =
-0.00336 -0.00647 -0.01113
AFIX 43
H20 2 0.82768 0.68763 0.04456 11.00000 -1.20000
AFIX 0
C21 1 0.93148 0.92448 0.36636 11.00000 0.02092 0.01831 0.01542 =
-0.00290 0.00106 -0.01168
C22 1 0.89091 0.89436 0.48128 11.00000 0.02495 0.03162 0.01208 =
0.00114 -0.00004 -0.01772
AFIX 23
H22a 2 0.83244 0.97721 0.51205 11.00000 -1.20000
H22b 2 0.97651 0.84858 0.52678 11.00000 -1.20000
AFIX 0
C23 1 0.81174 0.81175 0.48992 11.00000 0.02124 0.02389 0.00997 =
0.00473 -0.00266 -0.01202
C24 1 0.86880 0.69030 0.45247 11.00000 0.03495 0.02454 0.02212 =
-0.00058 0.00160 -0.01114
AFIX 43
H24 2 0.95688 0.65941 0.41658 11.00000 -1.20000
AFIX 0
C25 1 0.79680 0.61360 0.46752 11.00000 0.06790 0.02384 0.02714 =
0.00523 -0.01404 -0.02259
AFIX 43
H25 2 0.83532 0.53038 0.44134 11.00000 -1.20000
AFIX 0
C26 1 0.66989 0.65799 0.52025 11.00000 0.05330 0.05093 0.03132 =
0.01897 -0.01782 -0.04139
AFIX 43
H26 2 0.62194 0.60448 0.53194 11.00000 -1.20000
AFIX 0
C27 1 0.61239 0.77889 0.55595 11.00000 0.02837 0.05446 0.03155 =
0.01226 -0.00360 -0.02665
AFIX 43
H27 2 0.52412 0.80947 0.59153 11.00000 -1.20000
AFIX 0
C28 1 0.68180 0.85626 0.54055 11.00000 0.02186 0.03034 0.01865 =
0.00407 -0.00083 -0.01103
AFIX 43
H28 2 0.64073 0.94061 0.56464 11.00000 -1.20000
AFIX 0
B1 3 1.09742 0.94814 0.23208 11.00000 0.01979 0.01317 0.01493 =
-0.00391 0.00323 -0.00808
B2 3 0.86503 1.03505 0.17756 11.00000 0.02115 0.01648 0.01397 =
-0.00100 0.00084 -0.01006
HKLF 4
END
;
#===END
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform, pentane'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_5d_16srv084
_database_code_depnum_ccdc_archive 'CCDC 1551619'
_audit_update_record
;
2017-08-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2016-03-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common ?
_chemical_name_systematic
'Bis-(2-chlorophenyl)borinic acid benzylamine-4-phenylbutanoat '
_chemical_formula_moiety 'C29 H28 B Cl2 N O2'
_chemical_formula_sum 'C29 H28 B Cl2 N O2'
_chemical_formula_weight 504.23
_chemical_melting_point 409.7(5)
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'
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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.2006(2)
_cell_length_b 11.4729(4)
_cell_length_c 13.1121(4)
_cell_angle_alpha 101.570(3)
_cell_angle_beta 99.773(2)
_cell_angle_gamma 98.085(3)
_cell_volume 1314.23(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4447
_cell_measurement_temperature 120
_cell_measurement_theta_max 29.3480
_cell_measurement_theta_min 2.6960
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.274
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.83398
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.274
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.108
0.00 1.00 0.00 0.108
-1.00 0.00 1.00 0.184
1.00 0.00 -1.00 0.184
-1.00 0.00 -4.00 0.083
1.00 0.00 4.00 0.083
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.17
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0464
_diffrn_reflns_av_unetI/netI 0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 18221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.498
_diffrn_reflns_theta_min 2.516
_diffrn_ambient_temperature 120
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type 'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -41.00 49.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- -20.1554 57.0000 90.0000 180
#__ type_ start__ end____ width___ exp.time_
2 omega -24.00 22.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- -20.1554 -100.0000 -150.0000 92
#__ type_ start__ end____ width___ exp.time_
3 omega -24.00 63.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 -100.0000 60.0000 174
#__ type_ start__ end____ width___ exp.time_
4 omega 35.00 97.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 178.0000 -150.0000 124
#__ type_ start__ end____ width___ exp.time_
5 omega -1.00 90.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 57.0000 -30.0000 182
#__ type_ start__ end____ width___ exp.time_
6 omega -5.00 93.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 38.0000 -120.0000 196
#__ type_ start__ end____ width___ exp.time_
7 omega -5.00 93.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 38.0000 150.0000 196
#__ type_ start__ end____ width___ exp.time_
8 omega -52.00 46.00 0.5000 52.5300
omega____ theta____ kappa____ phi______ frames
- 20.7804 -38.0000 -150.0000 196
;
_diffrn_measurement_device kappa-diffractometer
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0738281000
_diffrn_orient_matrix_UB_12 -0.0103236000
_diffrn_orient_matrix_UB_13 0.0095209000
_diffrn_orient_matrix_UB_21 -0.0295983000
_diffrn_orient_matrix_UB_22 -0.0054464000
_diffrn_orient_matrix_UB_23 -0.0546820000
_diffrn_orient_matrix_UB_31 -0.0000004000
_diffrn_orient_matrix_UB_32 -0.0630948000
_diffrn_orient_matrix_UB_33 -0.0100326000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4561
_reflns_number_total 6009
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 27.42
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.512
_refine_diff_density_min -0.368
_refine_diff_density_rms 0.057
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 316
_refine_ls_number_reflns 6009
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0700
_refine_ls_R_factor_gt 0.0484
_refine_ls_restrained_S_all 1.029
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.4430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1119
_refine_ls_wR_factor_ref 0.1263
_refine_special_details
;
Amino H atoms - refall, other H atoms - riding (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
N(HA,HB), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27),
C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31756(6) 0.02519(4) 0.40959(4) 0.03316(14) Uani 1 1 d . . . . .
Cl2 Cl 0.49928(6) 0.24304(5) 0.12179(4) 0.03302(14) Uani 1 1 d . . . . .
O1 O 0.58768(14) 0.23844(11) 0.48657(10) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.50736(16) 0.40256(12) 0.56249(11) 0.0304(3) Uani 1 1 d . . . . .
N N 0.60901(17) 0.38361(14) 0.36830(12) 0.0227(3) Uani 1 1 d . . . . .
HA H 0.5894 0.3884 0.3006 0.027 Uiso 1 1 calc R . . . .
HB H 0.5650 0.4377 0.4045 0.027 Uiso 1 1 calc R . . . .
C1 C 0.5568(2) 0.31081(17) 0.56860(14) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.5874(2) 0.26814(18) 0.67031(15) 0.0288(4) Uani 1 1 d . . . . .
H2A H 0.6869 0.2479 0.6799 0.035 Uiso 1 1 calc R . . . .
H2B H 0.5160 0.1950 0.6639 0.035 Uiso 1 1 calc R . . . .
C3 C 0.5772(3) 0.3609(2) 0.76821(16) 0.0418(6) Uani 1 1 d . . . . .
H3A H 0.4859 0.3932 0.7532 0.050 Uiso 1 1 calc R . . . .
H3B H 0.6612 0.4274 0.7829 0.050 Uiso 1 1 calc R . . . .
C4 C 0.5775(3) 0.3094(2) 0.86734(17) 0.0409(6) Uani 1 1 d . . . . .
H4A H 0.5655 0.3724 0.9252 0.049 Uiso 1 1 calc R . . . .
H4B H 0.4915 0.2446 0.8531 0.049 Uiso 1 1 calc R . . . .
C5 C 0.7172(3) 0.2612(2) 0.90279(15) 0.0361(5) Uani 1 1 d . . . . .
C6 C 0.8403(3) 0.3388(3) 0.97056(19) 0.0606(8) Uani 1 1 d . . . . .
H6 H 0.8361 0.4202 0.9928 0.073 Uiso 1 1 calc R . . . .
C7 C 0.9668(4) 0.2979(5) 1.0049(3) 0.0906(14) Uani 1 1 d . . . . .
H7 H 1.0480 0.3513 1.0507 0.109 Uiso 1 1 calc R . . . .
C8 C 0.9758(4) 0.1784(6) 0.9727(3) 0.0991(17) Uani 1 1 d . . . . .
H8 H 1.0629 0.1507 0.9963 0.119 Uiso 1 1 calc R . . . .
C9 C 0.8529(4) 0.0976(4) 0.9035(2) 0.0738(11) Uani 1 1 d . . . . .
H9 H 0.8581 0.0163 0.8811 0.089 Uiso 1 1 calc R . . . .
C10 C 0.7242(3) 0.1403(2) 0.86933(18) 0.0435(6) Uani 1 1 d . . . . .
H10 H 0.6422 0.0876 0.8238 0.052 Uiso 1 1 calc R . . . .
C11 C 0.3518(2) 0.23834(17) 0.34527(14) 0.0240(4) Uani 1 1 d . . . . .
C12 C 0.2521(2) 0.13982(18) 0.35517(15) 0.0284(4) Uani 1 1 d . . . . .
C13 C 0.0970(2) 0.1248(2) 0.32284(17) 0.0349(5) Uani 1 1 d . . . . .
H13 H 0.0355 0.0568 0.3304 0.042 Uiso 1 1 calc R . . . .
C14 C 0.0352(2) 0.2109(2) 0.27981(17) 0.0367(5) Uani 1 1 d . . . . .
H14 H -0.0680 0.2009 0.2567 0.044 Uiso 1 1 calc R . . . .
C15 C 0.1283(2) 0.3124(2) 0.27120(16) 0.0346(5) Uani 1 1 d . . . . .
H15 H 0.0871 0.3722 0.2441 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2817(2) 0.32575(19) 0.30251(15) 0.0294(4) Uani 1 1 d . . . . .
H16 H 0.3417 0.3948 0.2954 0.035 Uiso 1 1 calc R . . . .
C17 C 0.5978(2) 0.15191(17) 0.29660(15) 0.0236(4) Uani 1 1 d . . . . .
C18 C 0.5883(2) 0.14209(18) 0.18783(15) 0.0271(4) Uani 1 1 d . . . . .
C19 C 0.6452(2) 0.0563(2) 0.12236(16) 0.0335(5) Uani 1 1 d . . . . .
H19 H 0.6381 0.0555 0.0506 0.040 Uiso 1 1 calc R . . . .
C20 C 0.7125(2) -0.0274(2) 0.16616(18) 0.0358(5) Uani 1 1 d . . . . .
H20 H 0.7510 -0.0857 0.1239 0.043 Uiso 1 1 calc R . . . .
C21 C 0.7224(2) -0.02430(19) 0.27310(18) 0.0335(5) Uani 1 1 d . . . . .
H21 H 0.7657 -0.0817 0.3026 0.040 Uiso 1 1 calc R . . . .
C22 C 0.6678(2) 0.06447(17) 0.33634(16) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.6781 0.0662 0.4084 0.033 Uiso 1 1 calc R . . . .
C23 C 0.7746(2) 0.41848(17) 0.40888(16) 0.0265(4) Uani 1 1 d . . . . .
H23A H 0.8218 0.3501 0.3859 0.032 Uiso 1 1 calc R . . . .
H23B H 0.7954 0.4388 0.4860 0.032 Uiso 1 1 calc R . . . .
C24 C 0.8409(2) 0.52483(17) 0.36974(16) 0.0256(4) Uani 1 1 d . . . . .
C25 C 0.8896(2) 0.63791(19) 0.43773(17) 0.0333(5) Uani 1 1 d . . . . .
H25 H 0.8794 0.6491 0.5082 0.040 Uiso 1 1 calc R . . . .
C26 C 0.9534(3) 0.7349(2) 0.4016(2) 0.0425(6) Uani 1 1 d . . . . .
H26 H 0.9873 0.8101 0.4484 0.051 Uiso 1 1 calc R . . . .
C27 C 0.9670(3) 0.7205(2) 0.2970(2) 0.0430(6) Uani 1 1 d . . . . .
H27 H 1.0107 0.7853 0.2732 0.052 Uiso 1 1 calc R . . . .
C28 C 0.9148(3) 0.6086(2) 0.2278(2) 0.0441(6) Uani 1 1 d . . . . .
H28 H 0.9213 0.5987 0.1566 0.053 Uiso 1 1 calc R . . . .
C29 C 0.8528(3) 0.5112(2) 0.26404(17) 0.0347(5) Uani 1 1 d . . . . .
H29 H 0.8189 0.4361 0.2171 0.042 Uiso 1 1 calc R . . . .
B B 0.5331(2) 0.25074(19) 0.37547(16) 0.0223(4) 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
Cl1 0.0296(3) 0.0286(3) 0.0444(3) 0.0136(2) 0.0111(2) 0.0040(2)
Cl2 0.0356(3) 0.0423(3) 0.0226(2) 0.0089(2) 0.00761(19) 0.0076(2)
O1 0.0227(7) 0.0253(7) 0.0221(6) 0.0051(5) 0.0057(5) 0.0062(5)
O2 0.0371(9) 0.0292(8) 0.0295(7) 0.0082(6) 0.0118(6) 0.0132(6)
N 0.0170(8) 0.0286(8) 0.0235(8) 0.0063(6) 0.0058(6) 0.0048(7)
C1 0.0195(10) 0.0239(10) 0.0247(9) 0.0029(7) 0.0066(7) 0.0012(8)
C2 0.0339(12) 0.0282(10) 0.0250(9) 0.0061(8) 0.0080(8) 0.0057(9)
C3 0.0679(18) 0.0367(12) 0.0262(10) 0.0095(9) 0.0164(10) 0.0158(12)
C4 0.0618(17) 0.0389(13) 0.0269(10) 0.0094(9) 0.0183(10) 0.0117(12)
C5 0.0450(14) 0.0420(13) 0.0220(10) 0.0112(9) 0.0114(9) -0.0012(10)
C6 0.0620(19) 0.079(2) 0.0295(12) 0.0123(13) 0.0063(12) -0.0212(16)
C7 0.048(2) 0.180(5) 0.0417(17) 0.042(2) 0.0064(14) -0.008(2)
C8 0.059(2) 0.230(6) 0.0490(19) 0.078(3) 0.0323(17) 0.071(3)
C9 0.100(3) 0.113(3) 0.0448(16) 0.0436(17) 0.0434(18) 0.067(2)
C10 0.0571(16) 0.0508(14) 0.0308(11) 0.0165(10) 0.0183(11) 0.0161(12)
C11 0.0201(10) 0.0283(10) 0.0221(9) 0.0020(7) 0.0067(7) 0.0019(8)
C12 0.0254(11) 0.0288(10) 0.0299(10) 0.0026(8) 0.0091(8) 0.0032(8)
C13 0.0232(11) 0.0357(12) 0.0397(11) -0.0038(9) 0.0117(9) -0.0034(9)
C14 0.0199(11) 0.0460(13) 0.0382(12) -0.0026(10) 0.0045(9) 0.0048(10)
C15 0.0277(12) 0.0446(13) 0.0324(11) 0.0077(9) 0.0042(9) 0.0128(10)
C16 0.0215(10) 0.0370(11) 0.0288(10) 0.0048(8) 0.0072(8) 0.0040(9)
C17 0.0158(9) 0.0263(10) 0.0269(9) 0.0035(8) 0.0067(7) -0.0009(8)
C18 0.0209(10) 0.0308(11) 0.0275(10) 0.0032(8) 0.0067(8) 0.0001(8)
C19 0.0237(11) 0.0421(12) 0.0293(10) -0.0024(9) 0.0111(8) -0.0034(9)
C20 0.0239(11) 0.0364(12) 0.0422(12) -0.0061(10) 0.0153(9) 0.0006(9)
C21 0.0219(11) 0.0292(11) 0.0487(13) 0.0039(9) 0.0117(9) 0.0037(9)
C22 0.0208(10) 0.0283(10) 0.0314(10) 0.0045(8) 0.0079(8) 0.0012(8)
C23 0.0177(10) 0.0276(10) 0.0342(10) 0.0084(8) 0.0045(8) 0.0032(8)
C24 0.0166(9) 0.0272(10) 0.0347(10) 0.0086(8) 0.0084(8) 0.0043(8)
C25 0.0321(12) 0.0328(11) 0.0335(11) 0.0069(9) 0.0080(9) 0.0011(9)
C26 0.0430(14) 0.0318(12) 0.0488(14) 0.0068(10) 0.0099(11) -0.0033(10)
C27 0.0363(14) 0.0382(13) 0.0597(15) 0.0193(11) 0.0191(11) 0.0013(10)
C28 0.0462(15) 0.0508(15) 0.0440(13) 0.0174(11) 0.0253(11) 0.0093(12)
C29 0.0365(13) 0.0329(11) 0.0357(11) 0.0054(9) 0.0151(9) 0.0037(10)
B 0.0183(11) 0.0265(11) 0.0225(10) 0.0066(8) 0.0054(8) 0.0027(9)
_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
Cl1 C12 1.748(2) . ?
Cl2 C18 1.786(2) . ?
O1 C1 1.319(2) . ?
O1 B 1.499(2) . ?
O2 C1 1.216(2) . ?
N C23 1.494(2) . ?
N B 1.613(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.520(3) . ?
C3 C4 1.532(3) . ?
C4 C5 1.509(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.382(3) . ?
C6 C7 1.355(5) . ?
C7 C8 1.370(6) . ?
C8 C9 1.407(6) . ?
C9 C10 1.384(4) . ?
C11 C12 1.394(3) . ?
C11 C16 1.422(3) . ?
C11 B 1.626(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.379(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.404(3) . ?
C17 B 1.624(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.387(3) . ?
C23 C24 1.508(3) . ?
C24 C25 1.384(3) . ?
C24 C29 1.388(3) . ?
C25 C26 1.389(3) . ?
C26 C27 1.377(3) . ?
C27 C28 1.383(3) . ?
C28 C29 1.388(3) . ?
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
C1 O1 B 120.69(15) . . ?
C23 N B 116.22(14) . . ?
O1 C1 C2 113.50(16) . . ?
O2 C1 O1 123.20(17) . . ?
O2 C1 C2 123.30(17) . . ?
C1 C2 C3 113.60(17) . . ?
C2 C3 C4 113.43(18) . . ?
C5 C4 C3 114.5(2) . . ?
C6 C5 C4 119.7(2) . . ?
C10 C5 C4 121.0(2) . . ?
C10 C5 C6 119.3(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 C8 120.4(3) . . ?
C7 C8 C9 119.8(3) . . ?
C10 C9 C8 119.3(3) . . ?
C5 C10 C9 120.1(3) . . ?
C12 C11 C16 114.22(18) . . ?
C12 C11 B 123.31(17) . . ?
C16 C11 B 122.43(18) . . ?
C11 C12 Cl1 120.75(15) . . ?
C13 C12 Cl1 115.71(17) . . ?
C13 C12 C11 123.5(2) . . ?
C14 C13 C12 119.8(2) . . ?
C13 C14 C15 119.2(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 122.7(2) . . ?
C18 C17 C22 114.11(17) . . ?
C18 C17 B 125.87(17) . . ?
C22 C17 B 120.00(16) . . ?
C17 C18 Cl2 120.85(15) . . ?
C19 C18 Cl2 114.67(15) . . ?
C19 C18 C17 124.48(19) . . ?
C20 C19 C18 118.6(2) . . ?
C19 C20 C21 119.78(19) . . ?
C20 C21 C22 119.9(2) . . ?
C21 C22 C17 123.07(19) . . ?
N C23 C24 111.83(15) . . ?
C25 C24 C23 120.94(18) . . ?
C25 C24 C29 118.68(19) . . ?
C29 C24 C23 120.38(17) . . ?
C24 C25 C26 120.6(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C27 C28 119.4(2) . . ?
C27 C28 C29 120.2(2) . . ?
C24 C29 C28 120.6(2) . . ?
O1 B N 107.01(14) . . ?
O1 B C11 112.72(16) . . ?
O1 B C17 107.00(15) . . ?
N B C11 108.56(15) . . ?
N B C17 107.88(16) . . ?
C17 B C11 113.39(15) . . ?
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
N HA Cl2 0.89 2.52 3.2265(16) 136.9 .
N HB O2 0.89 2.03 2.857(2) 154.6 2_666
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
16srv084.res created by SHELXL-2014/7
TITL 16srv084 in P-1 #2
CELL 0.71073 9.20065 11.472891 13.112127 101.5704 99.7727 98.0845
ZERR 2 0.000232 0.000411 0.000362 0.0027 0.0023 0.0025
LATT 1
SFAC C H B Cl N O
UNIT 58 56 2 4 2 4
EQIV $1 1-X,1-Y,1-Z
L.S. 7
PLAN 10
HTAB N O2_$1
HTAB N Cl2
fmap 2
acta
OMIT -3 55
OMIT 0 1 0
OMIT -1 1 0
OMIT 1 0 0
OMIT 0 -1 1
REM
REM
REM
WGHT 0.054000 0.443000
FVAR 2.20879
CL1 4 0.317558 0.025193 0.409586 11.00000 0.02959 0.02865 =
0.04441 0.01360 0.01110 0.00401
CL2 4 0.499283 0.243044 0.121794 11.00000 0.03555 0.04229 =
0.02261 0.00892 0.00761 0.00758
O1 6 0.587684 0.238445 0.486568 11.00000 0.02265 0.02534 =
0.02209 0.00508 0.00567 0.00617
O2 6 0.507363 0.402558 0.562490 11.00000 0.03706 0.02921 =
0.02951 0.00815 0.01177 0.01321
N 5 0.609012 0.383610 0.368300 11.00000 0.01697 0.02865 =
0.02348 0.00626 0.00582 0.00480
AFIX 23
HA 2 0.589388 0.388380 0.300572 11.00000 -1.20000
HB 2 0.565046 0.437746 0.404484 11.00000 -1.20000
AFIX 0
C1 1 0.556833 0.310808 0.568600 11.00000 0.01951 0.02387 =
0.02466 0.00289 0.00664 0.00119
C2 1 0.587389 0.268137 0.670311 11.00000 0.03389 0.02821 =
0.02504 0.00609 0.00804 0.00572
AFIX 23
H2A 2 0.686943 0.247927 0.679909 11.00000 -1.20000
H2B 2 0.516045 0.194966 0.663948 11.00000 -1.20000
AFIX 0
C3 1 0.577178 0.360922 0.768206 11.00000 0.06790 0.03666 =
0.02624 0.00950 0.01645 0.01583
AFIX 23
H3A 2 0.485929 0.393168 0.753199 11.00000 -1.20000
H3B 2 0.661237 0.427353 0.782883 11.00000 -1.20000
AFIX 0
C4 1 0.577454 0.309411 0.867335 11.00000 0.06177 0.03890 =
0.02686 0.00941 0.01833 0.01171
AFIX 23
H4A 2 0.565494 0.372402 0.925206 11.00000 -1.20000
H4B 2 0.491532 0.244649 0.853094 11.00000 -1.20000
AFIX 0
C5 1 0.717214 0.261204 0.902792 11.00000 0.04502 0.04205 =
0.02196 0.01121 0.01141 -0.00121
C6 1 0.840345 0.338778 0.970558 11.00000 0.06195 0.07883 =
0.02955 0.01232 0.00634 -0.02118
AFIX 43
H6 2 0.836103 0.420242 0.992802 11.00000 -1.20000
AFIX 0
C7 1 0.966792 0.297877 1.004928 11.00000 0.04772 0.17984 =
0.04172 0.04169 0.00637 -0.00812
AFIX 43
H7 2 1.047950 0.351278 1.050709 11.00000 -1.20000
AFIX 0
C8 1 0.975808 0.178363 0.972655 11.00000 0.05906 0.23047 =
0.04900 0.07755 0.03234 0.07132
AFIX 43
H8 2 1.062866 0.150743 0.996342 11.00000 -1.20000
AFIX 0
C9 1 0.852881 0.097563 0.903545 11.00000 0.09966 0.11288 =
0.04478 0.04357 0.04342 0.06667
AFIX 43
H9 2 0.858076 0.016323 0.881102 11.00000 -1.20000
AFIX 0
C10 1 0.724166 0.140291 0.869331 11.00000 0.05714 0.05081 =
0.03080 0.01647 0.01830 0.01606
AFIX 43
H10 2 0.642225 0.087591 0.823763 11.00000 -1.20000
AFIX 0
C11 1 0.351830 0.238342 0.345271 11.00000 0.02007 0.02834 =
0.02210 0.00198 0.00668 0.00195
C12 1 0.252074 0.139816 0.355172 11.00000 0.02544 0.02882 =
0.02986 0.00262 0.00913 0.00317
C13 1 0.096977 0.124831 0.322842 11.00000 0.02315 0.03568 =
0.03972 -0.00376 0.01167 -0.00342
AFIX 43
H13 2 0.035455 0.056804 0.330371 11.00000 -1.20000
AFIX 0
C14 1 0.035226 0.210870 0.279808 11.00000 0.01990 0.04596 =
0.03817 -0.00257 0.00447 0.00481
AFIX 43
H14 2 -0.068022 0.200851 0.256743 11.00000 -1.20000
AFIX 0
C15 1 0.128253 0.312392 0.271203 11.00000 0.02765 0.04455 =
0.03237 0.00774 0.00417 0.01277
AFIX 43
H15 2 0.087145 0.372176 0.244101 11.00000 -1.20000
AFIX 0
C16 1 0.281670 0.325752 0.302512 11.00000 0.02152 0.03705 =
0.02876 0.00481 0.00720 0.00399
AFIX 43
H16 2 0.341696 0.394757 0.295367 11.00000 -1.20000
AFIX 0
C17 1 0.597803 0.151906 0.296605 11.00000 0.01581 0.02629 =
0.02687 0.00348 0.00675 -0.00089
C18 1 0.588334 0.142087 0.187825 11.00000 0.02092 0.03077 =
0.02747 0.00323 0.00675 0.00007
C19 1 0.645249 0.056327 0.122358 11.00000 0.02365 0.04215 =
0.02929 -0.00239 0.01107 -0.00340
AFIX 43
H19 2 0.638102 0.055495 0.050601 11.00000 -1.20000
AFIX 0
C20 1 0.712468 -0.027389 0.166162 11.00000 0.02390 0.03636 =
0.04225 -0.00612 0.01529 0.00062
AFIX 43
H20 2 0.750962 -0.085718 0.123899 11.00000 -1.20000
AFIX 0
C21 1 0.722426 -0.024300 0.273099 11.00000 0.02193 0.02923 =
0.04867 0.00394 0.01168 0.00374
AFIX 43
H21 2 0.765677 -0.081680 0.302597 11.00000 -1.20000
AFIX 0
C22 1 0.667839 0.064475 0.336337 11.00000 0.02083 0.02830 =
0.03137 0.00449 0.00787 0.00117
AFIX 43
H22 2 0.678120 0.066152 0.408437 11.00000 -1.20000
AFIX 0
C23 1 0.774553 0.418479 0.408884 11.00000 0.01772 0.02757 =
0.03419 0.00838 0.00453 0.00316
AFIX 23
H23A 2 0.821782 0.350095 0.385859 11.00000 -1.20000
H23B 2 0.795373 0.438798 0.486013 11.00000 -1.20000
AFIX 0
C24 1 0.840884 0.524831 0.369744 11.00000 0.01662 0.02725 =
0.03474 0.00864 0.00842 0.00430
C25 1 0.889568 0.637909 0.437727 11.00000 0.03210 0.03280 =
0.03354 0.00685 0.00795 0.00112
AFIX 43
H25 2 0.879422 0.649059 0.508230 11.00000 -1.20000
AFIX 0
C26 1 0.953439 0.734898 0.401634 11.00000 0.04298 0.03184 =
0.04880 0.00684 0.00992 -0.00335
AFIX 43
H26 2 0.987312 0.810089 0.448427 11.00000 -1.20000
AFIX 0
C27 1 0.966954 0.720491 0.297042 11.00000 0.03627 0.03818 =
0.05969 0.01930 0.01915 0.00126
AFIX 43
H27 2 1.010723 0.785336 0.273218 11.00000 -1.20000
AFIX 0
C28 1 0.914799 0.608636 0.227753 11.00000 0.04624 0.05079 =
0.04403 0.01740 0.02535 0.00932
AFIX 43
H28 2 0.921310 0.598664 0.156612 11.00000 -1.20000
AFIX 0
C29 1 0.852765 0.511205 0.264041 11.00000 0.03648 0.03290 =
0.03573 0.00544 0.01510 0.00371
AFIX 43
H29 2 0.818860 0.436118 0.217090 11.00000 -1.20000
AFIX 0
B 3 0.533056 0.250736 0.375472 11.00000 0.01829 0.02647 =
0.02254 0.00660 0.00544 0.00267
HKLF 4
REM 16srv084 in P-1 #2
REM R1 = 0.0484 for 4561 Fo > 4sig(Fo) and 0.0700 for all 6009 data
REM 316 parameters refined using 0 restraints
END
WGHT 0.0538 0.4600
REM Highest difference peak 0.512, deepest hole -0.368, 1-sigma level 0.057
Q1 1 0.5460 0.1999 0.1286 11.00000 0.05 0.51
Q2 1 0.5050 0.2818 0.1574 11.00000 0.05 0.37
Q3 1 0.4530 0.2077 0.1217 11.00000 0.05 0.32
Q4 1 0.4968 0.2385 0.0877 11.00000 0.05 0.31
Q5 1 0.2538 0.3611 0.2602 11.00000 0.05 0.28
Q6 1 0.8280 0.0457 0.8725 11.00000 0.05 0.27
Q7 1 0.3205 0.1230 0.3953 11.00000 0.05 0.26
Q8 1 0.9720 0.2205 0.9672 11.00000 0.05 0.26
Q9 1 0.9654 0.1052 0.9427 11.00000 0.05 0.26
Q10 1 0.5602 0.1997 0.3174 11.00000 0.05 0.25
REM The information below was added by Olex2.
REM
REM R1 = 0.0484 for 4561 Fo > 4sig(Fo) and 0.0700 for all 19469 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.51, deepest hole -0.37
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0700
REM R1_gt = 0.0484
REM wR_ref = 0.1263
REM GOOF = 1.029
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 19469
REM Reflections_gt = 4561
REM Parameters = n/a
REM Hole = -0.37
REM Peak = 0.51
REM Flack = n/a
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_5b_15srv006
_database_code_depnum_ccdc_archive 'CCDC 1551617'
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2017-07-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic
'Bis(3,4,5-trifluorophenyl)-borinic acid benzylaminobenzoat'
_chemical_formula_moiety 'C26 H18 B F6 N O2'
_chemical_formula_sum 'C26 H18 B F6 N O2'
_chemical_formula_weight 501.22
_chemical_melting_point 471.7(1.5)
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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/n 1'
_space_group_name_Hall '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 10.1019(4)
_cell_length_b 11.7656(5)
_cell_length_c 19.5670(9)
_cell_angle_alpha 90
_cell_angle_beta 103.6902(15)
_cell_angle_gamma 90
_cell_volume 2259.56(17)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9970
_cell_measurement_temperature 120(2)
_cell_measurement_theta_max 27.47
_cell_measurement_theta_min 2.55
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.126
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9356
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0617 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.473
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description rhombohedron
_exptl_crystal_F_000 1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0030
0.00 1.00 -1.00 0.1190
-1.00 -3.00 3.00 0.0230
1.00 3.00 -3.00 0.1600
0.00 1.00 1.00 0.1460
-1.00 -3.00 1.00 0.0220
0.00 -1.00 -3.00 0.0800
-1.00 1.00 -3.00 0.0980
1.00 2.00 2.00 0.1540
1.00 -2.00 2.00 0.0230
-2.00 3.00 1.00 0.1370
2.00 -2.00 -1.00 0.0460
-3.00 0.00 1.00 0.1120
3.00 0.00 -1.00 0.1320
1.00 -1.00 -2.00 0.0490
_exptl_crystal_size_max 0.299
_exptl_crystal_size_mid 0.273
_exptl_crystal_size_min 0.243
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0276
_diffrn_reflns_av_unetI/netI 0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_number 29313
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 27.500
_diffrn_reflns_theta_max 27.505
_diffrn_reflns_theta_min 2.143
_diffrn_ambient_temperature 120.0
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4345
_reflns_number_total 5189
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.311
_refine_diff_density_min -0.220
_refine_diff_density_rms 0.043
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 346
_refine_ls_number_reflns 5189
_refine_ls_number_restraints 74
_refine_ls_R_factor_all 0.0469
_refine_ls_R_factor_gt 0.0373
_refine_ls_restrained_S_all 1.012
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+1.0370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0913
_refine_ls_wR_factor_ref 0.0976
_refine_special_details
;
Phenyl substituent at C(1) shows flipping disorder, which was
rationalised as two alternative positions for C(4), C(5), C(6),
C(7) and their hydrogens, with occupancies refined to 0.655(8)
and 0.345(8).
Amino H atoms: refall, other H atoms: riding model (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Restrained distances
C4A-C3 \\sim C4-C3
with sigma of 0.02
C5-C4 \\sim C5A-C4A
with sigma of 0.02
C7-C2 \\sim C7A-C2
with sigma of 0.02
C7-C6 \\sim C7A-C6A
with sigma of 0.02
C6-C5 \\sim C6A-C5A
with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
C2, C3, C4, C5, C6, C7, C4A, C5A, C6A, C7A
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=1-
FVAR(1)
Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(1)
Fixed Sof: H3B(0.6) H3A(0.4)
6.a Secondary CH2 refined with riding coordinates:
C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
C3(H3B), C3(H3A), C9(H9), C13(H13), C15(H15), C19(H19), C22(H22), C23(H23),
C24(H24), C25(H25), C26(H26), C4(H4), C5(H5), C6(H6), C7(H7), C4A(H4A),
C5A(H5A), C6A(H6A), C7A(H7A)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61098(11) 0.52102(8) 0.12885(5) 0.0446(2) Uani 1 1 d . . . . .
F2 F 0.77321(9) 0.34069(8) 0.12051(4) 0.0366(2) Uani 1 1 d . . . . .
F3 F 0.81047(8) 0.17785(7) 0.21906(4) 0.0333(2) Uani 1 1 d . . . . .
F4 F 0.13296(8) 0.65335(8) 0.30983(5) 0.0388(2) Uani 1 1 d . . . . .
F5 F -0.03428(8) 0.47521(9) 0.26732(5) 0.0444(2) Uani 1 1 d . . . . .
F6 F 0.07096(10) 0.26332(9) 0.26884(5) 0.0495(3) Uani 1 1 d . . . . .
O1 O 0.57651(9) 0.29427(7) 0.40671(4) 0.02166(19) Uani 1 1 d . . . . .
O2 O 0.50199(10) 0.36816(8) 0.49618(5) 0.0297(2) Uani 1 1 d . . . . .
N1 N 0.62540(10) 0.50364(9) 0.40316(6) 0.0197(2) Uani 1 1 d . . . . .
H1A H 0.6238(15) 0.5628(14) 0.3731(8) 0.026(4) Uiso 1 1 d . . . . .
H1B H 0.5813(17) 0.5320(14) 0.4361(9) 0.032(4) Uiso 1 1 d . . . . .
C1 C 0.55280(13) 0.29004(11) 0.47039(6) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.59971(13) 0.18264(11) 0.50843(6) 0.0227(3) Uani 1 1 d D U . . .
C3 C 0.66770(15) 0.09986(13) 0.48016(7) 0.0319(3) Uani 1 1 d D U . . .
H3B H 0.669117 0.104817 0.431880 0.038 Uiso 0.6 1 calc R . P A 2
H3A H 0.686686 0.110970 0.435344 0.038 Uiso 0.4 1 calc R . P B 1
C8 C 0.60188(12) 0.37505(10) 0.29205(6) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.57515(14) 0.45415(11) 0.23719(7) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.516480 0.516615 0.238972 0.029 Uiso 1 1 calc R . . . .
C10 C 0.63313(14) 0.44232(12) 0.18058(7) 0.0273(3) Uani 1 1 d . . . . .
C11 C 0.71445(13) 0.35090(12) 0.17512(7) 0.0254(3) Uani 1 1 d . . . . .
C12 C 0.73502(12) 0.26996(11) 0.22693(7) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.68254(12) 0.28116(11) 0.28549(6) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.701216 0.225021 0.321382 0.026 Uiso 1 1 calc R . . . .
C14 C 0.38210(13) 0.42380(11) 0.33925(6) 0.0213(3) Uani 1 1 d . . . . .
C15 C 0.32558(13) 0.53206(12) 0.33729(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H 0.382890 0.595546 0.352879 0.029 Uiso 1 1 calc R . . . .
C16 C 0.18678(14) 0.54798(12) 0.31287(7) 0.0273(3) Uani 1 1 d . . . . .
C17 C 0.10057(13) 0.45802(14) 0.29085(7) 0.0301(3) Uani 1 1 d . . . . .
C18 C 0.15585(14) 0.35121(14) 0.29222(7) 0.0316(3) Uani 1 1 d . . . . .
C19 C 0.29368(14) 0.33291(12) 0.31551(7) 0.0270(3) Uani 1 1 d . . . . .
H19 H 0.329107 0.258123 0.315490 0.032 Uiso 1 1 calc R . . . .
C20 C 0.77200(13) 0.47863(11) 0.43760(7) 0.0260(3) Uani 1 1 d . . . . .
H20A H 0.775860 0.427444 0.478179 0.031 Uiso 1 1 calc R . . . .
H20B H 0.814030 0.438379 0.403626 0.031 Uiso 1 1 calc R . . . .
C21 C 0.85307(12) 0.58405(11) 0.46259(6) 0.0218(3) Uani 1 1 d . . . . .
C22 C 0.94046(13) 0.62906(12) 0.42440(7) 0.0244(3) Uani 1 1 d . . . . .
H22 H 0.948087 0.593233 0.381993 0.029 Uiso 1 1 calc R . . . .
C23 C 1.01669(13) 0.72563(12) 0.44745(7) 0.0280(3) Uani 1 1 d . . . . .
H23 H 1.076387 0.755493 0.421005 0.034 Uiso 1 1 calc R . . . .
C24 C 1.00559(14) 0.77844(12) 0.50909(7) 0.0296(3) Uani 1 1 d . . . . .
H24 H 1.056954 0.845047 0.524838 0.036 Uiso 1 1 calc R . . . .
C25 C 0.91934(15) 0.73378(12) 0.54769(7) 0.0304(3) Uani 1 1 d . . . . .
H25 H 0.912169 0.769641 0.590164 0.037 Uiso 1 1 calc R . . . .
C26 C 0.84351(14) 0.63727(12) 0.52479(7) 0.0264(3) Uani 1 1 d . . . . .
H26 H 0.784653 0.607180 0.551635 0.032 Uiso 1 1 calc R . . . .
B1 B 0.54306(14) 0.39655(12) 0.36095(7) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.7084(8) 0.0000(8) 0.5175(5) 0.0336(13) Uani 0.655(8) 1 d D U P C 1
H4 H 0.751866 -0.059000 0.497823 0.040 Uiso 0.655(8) 1 calc R . P C 1
C5 C 0.6844(6) -0.0114(7) 0.5834(4) 0.0382(12) Uani 0.655(8) 1 d D U P C 1
H5 H 0.721813 -0.074505 0.611757 0.046 Uiso 0.655(8) 1 calc R . P C 1
C6 C 0.6065(6) 0.0676(3) 0.60933(18) 0.0412(9) Uani 0.655(8) 1 d D U P C 1
H6 H 0.584042 0.054495 0.653158 0.049 Uiso 0.655(8) 1 calc R . P C 1
C7 C 0.5614(5) 0.1654(3) 0.5716(2) 0.0295(8) Uani 0.655(8) 1 d D U P C 1
H7 H 0.506016 0.219069 0.588151 0.035 Uiso 0.655(8) 1 calc R . P C 1
C4A C 0.7339(19) 0.0099(15) 0.5195(10) 0.0336(13) Uani 0.345(8) 1 d D U P C 2
H4A H 0.788790 -0.039227 0.499286 0.040 Uiso 0.345(8) 1 calc R . P C 2
C5A C 0.7225(13) -0.0101(14) 0.5865(8) 0.0382(12) Uani 0.345(8) 1 d D U P C 2
H5A H 0.751679 -0.079848 0.609626 0.046 Uiso 0.345(8) 1 calc R . P C 2
C6A C 0.6680(9) 0.0733(7) 0.6185(4) 0.0412(9) Uani 0.345(8) 1 d D U P C 2
H6A H 0.669228 0.066889 0.667055 0.049 Uiso 0.345(8) 1 calc R . P C 2
C7A C 0.6105(8) 0.1677(8) 0.5812(4) 0.0295(8) Uani 0.345(8) 1 d D U P C 2
H7A H 0.576230 0.226043 0.605886 0.035 Uiso 0.345(8) 1 calc R . P C 2
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 0.0673(6) 0.0409(5) 0.0301(4) 0.0152(4) 0.0207(4) 0.0033(5)
F2 0.0376(5) 0.0519(6) 0.0262(4) -0.0067(4) 0.0189(4) -0.0098(4)
F3 0.0321(4) 0.0371(5) 0.0319(4) -0.0086(4) 0.0100(3) 0.0094(4)
F4 0.0292(4) 0.0413(5) 0.0469(5) 0.0075(4) 0.0108(4) 0.0131(4)
F5 0.0197(4) 0.0744(7) 0.0363(5) -0.0074(5) 0.0009(3) -0.0005(4)
F6 0.0381(5) 0.0562(6) 0.0510(6) -0.0205(5) 0.0040(4) -0.0209(5)
O1 0.0291(5) 0.0206(4) 0.0167(4) 0.0002(3) 0.0083(3) 0.0026(4)
O2 0.0377(5) 0.0287(5) 0.0268(5) -0.0046(4) 0.0156(4) 0.0043(4)
N1 0.0206(5) 0.0196(5) 0.0182(5) -0.0003(4) 0.0036(4) 0.0039(4)
C1 0.0227(6) 0.0248(6) 0.0182(6) -0.0032(5) 0.0075(5) -0.0031(5)
C2 0.0272(6) 0.0234(6) 0.0177(6) -0.0021(5) 0.0060(5) -0.0067(5)
C3 0.0411(8) 0.0345(8) 0.0232(6) 0.0079(6) 0.0137(6) 0.0104(6)
C8 0.0216(6) 0.0202(6) 0.0169(5) -0.0020(5) 0.0038(4) -0.0030(5)
C9 0.0290(7) 0.0210(6) 0.0227(6) 0.0000(5) 0.0069(5) 0.0009(5)
C10 0.0352(7) 0.0266(7) 0.0199(6) 0.0046(5) 0.0061(5) -0.0058(6)
C11 0.0247(6) 0.0353(7) 0.0182(6) -0.0064(5) 0.0092(5) -0.0092(5)
C12 0.0192(6) 0.0250(6) 0.0242(6) -0.0074(5) 0.0042(5) -0.0004(5)
C13 0.0236(6) 0.0230(6) 0.0181(6) -0.0013(5) 0.0039(5) -0.0002(5)
C14 0.0238(6) 0.0257(6) 0.0153(5) -0.0007(5) 0.0065(5) -0.0007(5)
C15 0.0228(6) 0.0271(7) 0.0227(6) 0.0000(5) 0.0072(5) -0.0011(5)
C16 0.0267(7) 0.0350(7) 0.0216(6) 0.0029(6) 0.0085(5) 0.0059(6)
C17 0.0195(6) 0.0526(9) 0.0178(6) -0.0022(6) 0.0033(5) -0.0010(6)
C18 0.0294(7) 0.0429(8) 0.0220(6) -0.0088(6) 0.0050(5) -0.0120(6)
C19 0.0313(7) 0.0291(7) 0.0209(6) -0.0046(5) 0.0064(5) -0.0030(6)
C20 0.0215(6) 0.0238(6) 0.0289(7) -0.0013(5) -0.0014(5) 0.0063(5)
C21 0.0192(6) 0.0217(6) 0.0212(6) 0.0003(5) -0.0014(5) 0.0062(5)
C22 0.0217(6) 0.0305(7) 0.0199(6) -0.0014(5) 0.0026(5) 0.0071(5)
C23 0.0236(6) 0.0316(7) 0.0282(7) 0.0035(6) 0.0048(5) 0.0022(5)
C24 0.0292(7) 0.0249(7) 0.0311(7) -0.0024(6) -0.0002(6) -0.0005(5)
C25 0.0379(8) 0.0297(7) 0.0225(6) -0.0058(6) 0.0047(6) 0.0026(6)
C26 0.0292(7) 0.0279(7) 0.0222(6) 0.0015(5) 0.0059(5) 0.0026(5)
B1 0.0236(6) 0.0188(6) 0.0175(6) -0.0010(5) 0.0051(5) 0.0011(5)
C4 0.037(3) 0.0312(17) 0.0344(10) 0.0094(12) 0.0117(19) 0.005(2)
C5 0.055(4) 0.0283(8) 0.0275(10) 0.0092(7) 0.001(2) -0.004(2)
C6 0.071(3) 0.0353(10) 0.0191(12) 0.0037(9) 0.0154(18) -0.0102(19)
C7 0.043(2) 0.0280(8) 0.0213(12) -0.0033(8) 0.0148(16) -0.0072(17)
C4A 0.037(3) 0.0312(17) 0.0344(10) 0.0094(12) 0.0117(19) 0.005(2)
C5A 0.055(4) 0.0283(8) 0.0275(10) 0.0092(7) 0.001(2) -0.004(2)
C6A 0.071(3) 0.0353(10) 0.0191(12) 0.0037(9) 0.0154(18) -0.0102(19)
C7A 0.043(2) 0.0280(8) 0.0213(12) -0.0033(8) 0.0148(16) -0.0072(17)
_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 C10 1.3508(15) . ?
F2 C11 1.3450(14) . ?
F3 C12 1.3546(15) . ?
F4 C16 1.3493(16) . ?
F5 C17 1.3460(15) . ?
F6 C18 1.3521(16) . ?
O1 C1 1.3243(14) . ?
O1 B1 1.4902(16) . ?
O2 C1 1.2189(16) . ?
N1 C20 1.5039(16) . ?
N1 B1 1.6238(17) . ?
C1 C2 1.4861(18) . ?
C2 C3 1.3806(19) . ?
C2 C7 1.394(4) . ?
C2 C7A 1.414(8) . ?
C3 C4 1.394(7) . ?
C3 C4A 1.384(13) . ?
C8 C9 1.3979(17) . ?
C8 C13 1.3966(17) . ?
C8 B1 1.6167(18) . ?
C9 C10 1.3771(18) . ?
C10 C11 1.373(2) . ?
C11 C12 1.3704(19) . ?
C12 C13 1.3779(17) . ?
C14 C15 1.3928(19) . ?
C14 C19 1.4002(18) . ?
C14 B1 1.6125(18) . ?
C15 C16 1.3828(18) . ?
C16 C17 1.374(2) . ?
C17 C18 1.373(2) . ?
C18 C19 1.376(2) . ?
C20 C21 1.5029(18) . ?
C21 C22 1.3894(18) . ?
C21 C26 1.3921(18) . ?
C22 C23 1.3868(19) . ?
C23 C24 1.385(2) . ?
C24 C25 1.385(2) . ?
C25 C26 1.384(2) . ?
C4 C5 1.373(7) . ?
C5 C6 1.390(6) . ?
C6 C7 1.385(5) . ?
C4A C5A 1.362(13) . ?
C5A C6A 1.350(12) . ?
C6A C7A 1.380(9) . ?
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
C1 O1 B1 122.00(10) . . ?
C20 N1 B1 114.06(10) . . ?
O1 C1 C2 113.33(11) . . ?
O2 C1 O1 123.29(12) . . ?
O2 C1 C2 123.33(11) . . ?
C3 C2 C1 121.94(11) . . ?
C3 C2 C7 121.4(2) . . ?
C3 C2 C7A 112.9(4) . . ?
C7 C2 C1 116.4(2) . . ?
C7A C2 C1 123.3(4) . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 C4A 122.5(9) . . ?
C9 C8 B1 119.60(11) . . ?
C13 C8 C9 117.83(11) . . ?
C13 C8 B1 122.55(11) . . ?
C10 C9 C8 120.59(12) . . ?
F1 C10 C9 120.45(13) . . ?
F1 C10 C11 118.35(12) . . ?
C11 C10 C9 121.19(12) . . ?
F2 C11 C10 121.10(12) . . ?
F2 C11 C12 120.50(12) . . ?
C12 C11 C10 118.41(11) . . ?
F3 C12 C11 117.57(11) . . ?
F3 C12 C13 120.57(12) . . ?
C11 C12 C13 121.86(12) . . ?
C12 C13 C8 119.99(12) . . ?
C15 C14 C19 117.65(12) . . ?
C15 C14 B1 124.78(11) . . ?
C19 C14 B1 117.38(12) . . ?
C16 C15 C14 120.59(13) . . ?
F4 C16 C15 120.31(13) . . ?
F4 C16 C17 118.37(12) . . ?
C17 C16 C15 121.32(13) . . ?
F5 C17 C16 120.45(14) . . ?
F5 C17 C18 121.21(13) . . ?
C18 C17 C16 118.32(12) . . ?
F6 C18 C17 118.10(13) . . ?
F6 C18 C19 120.24(14) . . ?
C17 C18 C19 121.66(13) . . ?
C18 C19 C14 120.44(13) . . ?
C21 C20 N1 112.79(10) . . ?
C22 C21 C20 120.41(12) . . ?
C22 C21 C26 118.89(12) . . ?
C26 C21 C20 120.69(12) . . ?
C23 C22 C21 120.80(12) . . ?
C24 C23 C22 119.85(13) . . ?
C25 C24 C23 119.73(13) . . ?
C26 C25 C24 120.43(13) . . ?
C25 C26 C21 120.30(13) . . ?
O1 B1 N1 107.76(9) . . ?
O1 B1 C8 107.39(10) . . ?
O1 B1 C14 112.94(10) . . ?
C8 B1 N1 107.49(10) . . ?
C14 B1 N1 110.05(10) . . ?
C14 B1 C8 110.99(10) . . ?
C5 C4 C3 118.6(9) . . ?
C4 C5 C6 121.2(8) . . ?
C7 C6 C5 120.3(5) . . ?
C6 C7 C2 117.9(3) . . ?
C5A C4A C3 121.8(17) . . ?
C6A C5A C4A 117.2(17) . . ?
C5A C6A C7A 120.4(10) . . ?
C6A C7A C2 123.7(7) . . ?
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
N1 H1B O2 0.928(17) 2.091(18) 3.0016(14) 166.8(15) 3_666
C23 H23 F4 0.95 2.66 3.2941(17) 124.4 1_655
_shelx_res_file
;
TITL 14srv006 in P21/n #14
15srv006.res
created by SHELXL-2016/6 at 15:01:07 on 15-Jul-2017
REM reset to P21/n #14
CELL 0.71073 10.1019 11.7656 19.567 90 103.6902 90
ZERR 4 0.0004 0.0005 0.0009 0 0.0015 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H B F N O
UNIT 104 72 4 24 4 8
EQIV $1 1-X,1-Y,1-Z
EQIV $2 1+X,+Y,+Z
SADI C4A C3 C4 C3
SADI C5 C4 C5A C4A
SADI C7 C2 C7A C2
SADI C7 C6 C7A C6A
SADI C6 C5 C6A C5A
RIGU C2 C3 C4 C5 C6 C7 C4A C5A C6A C7A
EADP C4 C4A
EADP C5 C5A
EADP C6 C6A
EADP C7 C7A
L.S. 7
PLAN 7
TEMP -153.15
HTAB N1 O2_$1
HTAB C23 F4_$2
BOND
fmap 2 53
acta 55
REM
REM
REM
WGHT 0.044000 1.037000
FVAR 0.12098 0.65474
F1 4 0.610983 0.521021 0.128853 11.00000 0.06728 0.04093 =
0.03008 0.01518 0.02068 0.00333
F2 4 0.773207 0.340693 0.120506 11.00000 0.03755 0.05187 =
0.02619 -0.00673 0.01888 -0.00977
F3 4 0.810472 0.177848 0.219062 11.00000 0.03211 0.03706 =
0.03191 -0.00863 0.00997 0.00939
F4 4 0.132959 0.653347 0.309826 11.00000 0.02916 0.04125 =
0.04694 0.00752 0.01081 0.01307
F5 4 -0.034279 0.475206 0.267325 11.00000 0.01969 0.07437 =
0.03626 -0.00738 0.00089 -0.00050
F6 4 0.070963 0.263317 0.268840 11.00000 0.03807 0.05623 =
0.05097 -0.02054 0.00399 -0.02094
O1 6 0.576511 0.294271 0.406710 11.00000 0.02909 0.02062 =
0.01670 0.00020 0.00826 0.00263
O2 6 0.501987 0.368162 0.496181 11.00000 0.03771 0.02871 =
0.02681 -0.00457 0.01562 0.00428
N1 5 0.625397 0.503645 0.403161 11.00000 0.02059 0.01962 =
0.01825 -0.00028 0.00359 0.00386
H1A 2 0.623766 0.562803 0.373056 11.00000 0.02569
H1B 2 0.581341 0.532012 0.436095 11.00000 0.03152
C1 1 0.552797 0.290035 0.470390 11.00000 0.02268 0.02480 =
0.01819 -0.00322 0.00754 -0.00307
C2 1 0.599708 0.182635 0.508430 11.00000 0.02725 0.02338 =
0.01770 -0.00213 0.00602 -0.00672
C3 1 0.667699 0.099862 0.480161 11.00000 0.04111 0.03449 =
0.02323 0.00794 0.01375 0.01044
PART 2
AFIX 43
H3B 2 0.669117 0.104817 0.431880 10.60000 -1.20000
AFIX 43
PART 0
PART 1
H3A 2 0.686686 0.110970 0.435344 10.40000 -1.20000
AFIX 0
PART 0
C8 1 0.601877 0.375054 0.292049 11.00000 0.02159 0.02016 =
0.01690 -0.00204 0.00381 -0.00304
C9 1 0.575155 0.454149 0.237188 11.00000 0.02900 0.02096 =
0.02267 -0.00004 0.00692 0.00089
AFIX 43
H9 2 0.516480 0.516615 0.238972 11.00000 -1.20000
AFIX 0
C10 1 0.633131 0.442320 0.180576 11.00000 0.03523 0.02664 =
0.01995 0.00459 0.00610 -0.00578
C11 1 0.714448 0.350904 0.175122 11.00000 0.02469 0.03528 =
0.01821 -0.00640 0.00922 -0.00918
C12 1 0.735020 0.269963 0.226932 11.00000 0.01924 0.02502 =
0.02422 -0.00743 0.00421 -0.00044
C13 1 0.682537 0.281160 0.285485 11.00000 0.02360 0.02297 =
0.01808 -0.00133 0.00390 -0.00016
AFIX 43
H13 2 0.701216 0.225021 0.321382 11.00000 -1.20000
AFIX 0
C14 1 0.382101 0.423796 0.339251 11.00000 0.02384 0.02566 =
0.01530 -0.00071 0.00651 -0.00071
C15 1 0.325577 0.532063 0.337295 11.00000 0.02281 0.02711 =
0.02274 -0.00004 0.00721 -0.00109
AFIX 43
H15 2 0.382890 0.595546 0.352879 11.00000 -1.20000
AFIX 0
C16 1 0.186785 0.547981 0.312873 11.00000 0.02666 0.03504 =
0.02156 0.00289 0.00849 0.00589
C17 1 0.100573 0.458025 0.290845 11.00000 0.01946 0.05263 =
0.01781 -0.00223 0.00335 -0.00104
C18 1 0.155847 0.351208 0.292223 11.00000 0.02944 0.04290 =
0.02198 -0.00881 0.00499 -0.01196
C19 1 0.293677 0.332914 0.315512 11.00000 0.03129 0.02907 =
0.02091 -0.00456 0.00643 -0.00295
AFIX 43
H19 2 0.329107 0.258123 0.315490 11.00000 -1.20000
AFIX 0
C20 1 0.772001 0.478635 0.437600 11.00000 0.02151 0.02379 =
0.02890 -0.00132 -0.00138 0.00626
AFIX 23
H20A 2 0.775860 0.427444 0.478179 11.00000 -1.20000
H20B 2 0.814030 0.438379 0.403626 11.00000 -1.20000
AFIX 0
C21 1 0.853066 0.584053 0.462594 11.00000 0.01922 0.02174 =
0.02119 0.00035 -0.00141 0.00617
C22 1 0.940461 0.629056 0.424404 11.00000 0.02166 0.03053 =
0.01992 -0.00136 0.00258 0.00715
AFIX 43
H22 2 0.948087 0.593233 0.381993 11.00000 -1.20000
AFIX 0
C23 1 1.016691 0.725633 0.447448 11.00000 0.02356 0.03160 =
0.02816 0.00348 0.00477 0.00224
AFIX 43
H23 2 1.076387 0.755493 0.421005 11.00000 -1.20000
AFIX 0
C24 1 1.005594 0.778445 0.509092 11.00000 0.02923 0.02492 =
0.03111 -0.00241 -0.00021 -0.00046
AFIX 43
H24 2 1.056954 0.845047 0.524838 11.00000 -1.20000
AFIX 0
C25 1 0.919336 0.733784 0.547687 11.00000 0.03793 0.02965 =
0.02246 -0.00583 0.00473 0.00261
AFIX 43
H25 2 0.912169 0.769641 0.590164 11.00000 -1.20000
AFIX 0
C26 1 0.843506 0.637268 0.524790 11.00000 0.02921 0.02785 =
0.02218 0.00153 0.00594 0.00256
AFIX 43
H26 2 0.784653 0.607180 0.551635 11.00000 -1.20000
AFIX 0
B1 3 0.543062 0.396549 0.360947 11.00000 0.02355 0.01879 =
0.01751 -0.00104 0.00509 0.00112
PART 1
C4 1 0.708423 -0.000030 0.517515 21.00000 0.03691 0.03122 =
0.03437 0.00940 0.01170 0.00496
AFIX 43
H4 2 0.751866 -0.059000 0.497823 21.00000 -1.20000
AFIX 0
C5 1 0.684425 -0.011418 0.583388 21.00000 0.05461 0.02826 =
0.02747 0.00920 0.00097 -0.00398
AFIX 43
H5 2 0.721813 -0.074505 0.611757 21.00000 -1.20000
AFIX 0
C6 1 0.606477 0.067607 0.609333 21.00000 0.07148 0.03525 =
0.01908 0.00372 0.01542 -0.01024
AFIX 43
H6 2 0.584042 0.054495 0.653158 21.00000 -1.20000
AFIX 0
C7 1 0.561360 0.165409 0.571558 21.00000 0.04299 0.02796 =
0.02129 -0.00329 0.01479 -0.00721
AFIX 43
H7 2 0.506016 0.219069 0.588151 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C4A 1 0.733891 0.009909 0.519521 -21.00000 0.03691 0.03122 =
0.03437 0.00940 0.01170 0.00496
AFIX 43
H4A 2 0.788790 -0.039227 0.499286 -21.00000 -1.20000
AFIX 0
C5A 1 0.722489 -0.010105 0.586460 -21.00000 0.05461 0.02826 =
0.02747 0.00920 0.00097 -0.00398
AFIX 43
H5A 2 0.751679 -0.079848 0.609626 -21.00000 -1.20000
AFIX 0
C6A 1 0.667990 0.073280 0.618509 -21.00000 0.07148 0.03525 =
0.01908 0.00372 0.01542 -0.01024
AFIX 43
H6A 2 0.669228 0.066889 0.667055 -21.00000 -1.20000
AFIX 0
C7A 1 0.610503 0.167724 0.581231 -21.00000 0.04299 0.02796 =
0.02129 -0.00329 0.01479 -0.00721
AFIX 43
H7A 2 0.576230 0.226043 0.605886 -21.00000 -1.20000
AFIX 0
HKLF 4
REM 14srv006 in P21/n #14
REM R1 = 0.0373 for 4345 Fo > 4sig(Fo) and 0.0469 for all 5189 data
REM 346 parameters refined using 74 restraints
END
WGHT 0.0433 1.0329
REM Highest difference peak 0.311, deepest hole -0.220, 1-sigma level 0.043
Q1 1 0.5662 0.3816 0.3220 11.00000 0.05 0.31
Q2 1 0.4582 0.4151 0.3490 11.00000 0.05 0.28
Q3 1 0.2530 0.5354 0.3386 11.00000 0.05 0.21
Q4 1 0.1473 0.5023 0.2865 11.00000 0.05 0.20
Q5 1 0.8830 0.6178 0.4377 11.00000 0.05 0.20
Q6 1 0.3636 0.4786 0.3233 11.00000 0.05 0.20
Q7 1 0.6400 0.4604 0.2179 11.00000 0.05 0.19
;
_shelx_res_checksum 54374
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_4b_15srv104
_database_code_depnum_ccdc_archive 'CCDC 1551615'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2015-04-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic
; Bis-3,4,5-trifluorophenylborinic acid ethylenediamine complex
;
_chemical_formula_moiety 'C14 H13 B F6 N2 O,0.5(C D Cl3)'
_chemical_formula_sum 'C14.5 H13 B Cl1.5 D0.5 F6 N2 O'
_chemical_formula_weight 410.26
_chemical_absolute_configuration ?
_chemical_melting_point 363.7(2.5)
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'
D D 0.0000 0.0000 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 7
_space_group_name_H-M_alt 'P 1 c 1'
_space_group_name_Hall 'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
_cell_length_a 11.7500(5)
_cell_length_b 11.0269(4)
_cell_length_c 13.1973(5)
_cell_angle_alpha 90
_cell_angle_beta 97.3307(14)
_cell_angle_gamma 90
_cell_volume 1695.95(11)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9967
_cell_measurement_temperature 120
_cell_measurement_theta_max 29.27
_cell_measurement_theta_min 2.42
_shelx_estimated_absorpt_T_max 0.905
_shelx_estimated_absorpt_T_min 0.841
_exptl_absorpt_coefficient_mu 0.373
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9440
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.607
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 828
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 2.00 -1.00 0.1490
-1.00 0.00 2.00 0.1030
1.00 1.00 -2.00 0.1510
-1.00 1.00 1.00 0.1680
0.00 2.00 -1.00 0.2330
3.00 0.00 -2.00 0.1620
-1.00 -1.00 2.00 0.1290
-2.00 -1.00 3.00 0.1060
-1.00 2.00 -1.00 0.2440
-1.00 0.00 1.00 0.1110
-3.00 2.00 1.00 0.1900
3.00 -1.00 -2.00 0.1730
0.00 -1.00 1.00 0.1680
1.00 -2.00 -3.00 0.1020
0.00 -3.00 -1.00 0.1310
0.00 3.00 1.00 0.1930
-3.00 1.00 -2.00 0.2180
0.00 1.00 -2.00 0.1800
3.00 1.00 -1.00 0.1800
0.00 -1.00 3.00 0.1850
-3.00 -1.00 1.00 0.1800
0.00 1.00 -3.00 0.1700
-1.00 0.00 -3.00 0.1520
3.00 1.00 3.00 0.2200
1.00 2.00 3.00 0.1370
0.00 -2.00 -3.00 0.0840
_exptl_crystal_size_max 0.481
_exptl_crystal_size_mid 0.336
_exptl_crystal_size_min 0.274
_exptl_special_details
;
Data were collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of narrow-frame \w-scans (scan
width 0.5\%, 10s exposure), every run at a different \f angle.
One run of \f-scans (scan width 1\%, 1s exposure) was used for
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_exptl_twin_twinlaw_details '-1 0 0 0 -1 0 0 0 -1'
_diffrn_reflns_av_R_equivalents 0.0288
_diffrn_reflns_av_unetI/netI 0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 35272
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.325
_diffrn_reflns_theta_min 2.415
_diffrn_ambient_temperature 120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'ImuS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.997
_reflns_Friedel_fraction_full 1.000
_reflns_Friedel_fraction_max 0.998
_reflns_number_gt 8294
_reflns_number_total 9254
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.501
_refine_diff_density_min -0.634
_refine_diff_density_rms 0.064
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack 0.39(10)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 553
_refine_ls_number_reflns 9254
_refine_ls_number_restraints 57
_refine_ls_R_factor_all 0.0535
_refine_ls_R_factor_gt 0.0459
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.7700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1211
_refine_ls_wR_factor_ref 0.1267
_refine_special_details
;Refined as a 2-component inversion twin, BASF = 0.39(10).
The CDCl~3~ molecule is disordered. The minor orientation (15%)
comprises C(2S), D(2), Cl(6), Cl(7) and Cl(8). The major
orientation includes C(1S) with D(1) and Cl(1) (85%), while
two other Cl atoms are further disordered: Cl(2) and Cl(3) have
occupancies of 70%, Cl(4) and Cl(5) of 15%.
One trifluorophenyl group at B(1) shows a flipping disorder:
C(4), C(5), C(6), F(2) and F(3) are disordered between positions
A and B with occupancies refined to 57.8(8) and 42.2(8)%,
respectively. Hydroxyl and amino H atoms - refall, other H atoms
- riding model (constr).,Twin
;
_olex2_refinement_description
;
1. Twinned data refinement
Scales: 0.61(10) 0.39(10)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All O(H) groups
3. Restrained distances
C6A-C1 \\sim C6B-C1
with sigma of 0.02
C4A-C3 \\sim C4B-C3
with sigma of 0.02
F2A-C4A \\sim F2B-C4B
with sigma of 0.02
Cl4-C1S \\sim Cl2-C1S \\sim Cl3-C1S \\sim Cl5-C1S \\sim Cl1-C1S \\sim Cl8-C2S
\\sim Cl6-C2S \\sim Cl7-C2S
with sigma of 0.02
C6A-C5A \\sim C6B-C5B
with sigma of 0.02
C5A-C4A \\sim C5B-C4B
with sigma of 0.02
F3A-C5A \\sim F3B-C5B
with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(C6A) = Uiso(C6B)
Uiso(C4B) = Uiso(C4A)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(C2S) = Uanis(C1S)
Uanis(C5B) = Uanis(C5A)
5. Rigid body (RIGU) restrains
F1, C1, C2, C3, F2A, F3A, C4A, C5A, C6A, F2B, F3B, C4B, C5B, C6B
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
Sof(F2B)=Sof(F3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
Sof(F2A)=Sof(F3A)=Sof(C4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
Fixed Sof: Cl6(0.15) Cl7(0.15) Cl8(0.15) C2S(0.15) D2(0.15) C1S(0.85)
D1(0.85) Cl1(0.85) Cl2(0.7) Cl3(0.7) Cl4(0.15) Cl5(0.15)
7.a Riding coordinates:
C2S(D2), C1S(D1), C6A(H6A), C6B(H6B)
7.b Secondary CH2 refined with riding coordinates:
C27(H27A,H27B), C28(H28A,H28B), C7(H7A,H7B), C8(H8A,H8B)
7.c Aromatic/amide H refined with riding coordinates:
C16(H16), C20(H20), C22(H22), C26(H26), C2(H2), C10(H10), C14(H14)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl6 Cl -0.0838(10) 0.3964(11) 0.2501(10) 0.047(2) Uiso 0.15 1 d D . P A 3
Cl7 Cl -0.1780(9) 0.1702(8) 0.2722(19) 0.125(8) Uani 0.15 1 d D . P A 3
Cl8 Cl 0.0435(11) 0.2473(9) 0.4143(7) 0.072(3) Uani 0.15 1 d D . P A 3
C2S C -0.0476(19) 0.2452(19) 0.2934(19) 0.0496(13) Uani 0.15 1 d D . P A 3
D2 D -0.0006 0.2119 0.2419 0.060 Uiso 0.15 1 d R . P A 3
C1S C -0.0483(5) 0.2880(5) 0.3630(5) 0.0496(13) Uani 0.85 1 d D . P . .
D1 D -0.0159 0.3330 0.4260 0.060 Uiso 0.85 1 d R . P B 1
Cl1 Cl -0.0429(3) 0.3716(3) 0.2527(2) 0.1037(12) Uani 0.85 1 d D . P C 1
Cl2 Cl -0.1936(2) 0.2955(3) 0.3911(3) 0.0831(8) Uani 0.7 1 d D . P C 1
Cl3 Cl -0.0052(2) 0.14034(18) 0.36495(18) 0.0681(6) Uani 0.7 1 d D . P C 1
Cl4 Cl -0.1688(6) 0.2074(8) 0.3790(7) 0.0441(17) Uani 0.15 1 d D . P C 2
Cl5 Cl 0.0525(9) 0.1727(9) 0.3203(8) 0.057(2) Uiso 0.15 1 d D . P C 2
F7 F 0.5340(2) 1.16908(17) 0.17500(15) 0.0316(5) Uani 1 1 d . . . . .
F8 F 0.5406(2) 1.29059(16) 0.35434(16) 0.0291(5) Uani 1 1 d . . . . .
F9 F 0.58267(19) 1.16952(18) 0.53195(14) 0.0252(4) Uani 1 1 d . . . . .
F10 F 1.03479(18) 0.8811(3) 0.40980(19) 0.0415(6) Uani 1 1 d . . . . .
F11 F 1.0960(2) 0.6671(3) 0.4957(2) 0.0522(8) Uani 1 1 d . . . . .
F12 F 0.9341(2) 0.5006(3) 0.5237(2) 0.0475(7) Uani 1 1 d . . . . .
O2 O 0.53378(18) 0.71442(19) 0.41693(16) 0.0140(4) Uani 1 1 d . . . . .
H2C H 0.559(4) 0.675(4) 0.461(3) 0.017 Uiso 1 1 d R . . . .
N3 N 0.5932(2) 0.7190(2) 0.24470(18) 0.0106(4) Uani 1 1 d . . . . .
H3A H 0.526(3) 0.743(3) 0.215(2) 0.002(7) Uiso 1 1 d . . . . .
H3B H 0.655(4) 0.764(4) 0.202(4) 0.035(12) Uiso 1 1 d . . . . .
N4 N 0.5924(3) 0.4148(2) 0.1078(2) 0.0196(5) Uani 1 1 d . . . . .
H4A H 0.662(4) 0.394(4) 0.138(4) 0.027(11) Uiso 1 1 d . . . . .
H4B H 0.545(5) 0.379(5) 0.135(5) 0.051(16) Uiso 1 1 d . . . . .
C15 C 0.5969(2) 0.9178(2) 0.3535(2) 0.0114(5) Uani 1 1 d . . . . .
C16 C 0.5747(3) 0.9830(3) 0.2620(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.5723 0.9420 0.1984 0.019 Uiso 1 1 calc R . . . .
C17 C 0.5562(3) 1.1067(3) 0.2639(2) 0.0187(6) Uani 1 1 d . . . . .
C18 C 0.5587(3) 1.1697(3) 0.3536(2) 0.0185(6) Uani 1 1 d . . . . .
C19 C 0.5814(3) 1.1061(3) 0.4438(2) 0.0161(6) Uani 1 1 d . . . . .
C20 C 0.6003(2) 0.9826(3) 0.4450(2) 0.0135(5) Uani 1 1 d . . . . .
H20 H 0.6159 0.9412 0.5084 0.016 Uiso 1 1 calc R . . . .
C21 C 0.7516(2) 0.7423(3) 0.4037(2) 0.0135(5) Uani 1 1 d . . . . .
C22 C 0.8379(3) 0.8271(3) 0.3914(2) 0.0189(6) Uani 1 1 d . . . . .
H22 H 0.8180 0.9038 0.3616 0.023 Uiso 1 1 calc R . . . .
C23 C 0.9520(3) 0.7993(4) 0.4227(3) 0.0269(7) Uani 1 1 d . . . . .
C24 C 0.9842(3) 0.6912(4) 0.4665(3) 0.0335(9) Uani 1 1 d . . . . .
C25 C 0.9010(3) 0.6081(4) 0.4799(3) 0.0303(8) Uani 1 1 d . . . . .
C26 C 0.7857(3) 0.6312(3) 0.4489(2) 0.0201(6) Uani 1 1 d . . . . .
H26 H 0.7298 0.5714 0.4584 0.024 Uiso 1 1 calc R . . . .
C27 C 0.6018(3) 0.5851(2) 0.2334(2) 0.0141(5) Uani 1 1 d . . . . .
H27A H 0.5421 0.5455 0.2685 0.017 Uiso 1 1 calc R . . . .
H27B H 0.6777 0.5575 0.2668 0.017 Uiso 1 1 calc R . . . .
C28 C 0.5870(3) 0.5466(3) 0.1211(2) 0.0150(5) Uani 1 1 d . . . . .
H28A H 0.5121 0.5765 0.0875 0.018 Uiso 1 1 calc R . . . .
H28B H 0.6479 0.5851 0.0867 0.018 Uiso 1 1 calc R . . . .
B2 B 0.6181(3) 0.7717(3) 0.3612(2) 0.0104(5) Uani 1 1 d . . . . .
F1 F 0.31953(18) 0.33589(18) 0.07665(15) 0.0251(4) Uani 1 1 d . U . . .
F4 F -0.15455(18) 0.6673(3) 0.1763(2) 0.0440(7) Uani 1 1 d . . . . .
F5 F -0.1925(2) 0.8987(3) 0.1178(2) 0.0524(8) Uani 1 1 d . . . . .
F6 F -0.0124(2) 1.0521(2) 0.11094(19) 0.0447(7) Uani 1 1 d . . . . .
O1 O 0.35998(17) 0.78212(18) 0.19034(16) 0.0131(4) Uani 1 1 d . . . . .
H1 H 0.336(4) 0.830(4) 0.134(4) 0.032(11) Uiso 1 1 d . . . . .
N1 N 0.2996(2) 0.7820(2) 0.36277(18) 0.0109(4) Uani 1 1 d . . . . .
H1A H 0.370(4) 0.756(4) 0.383(4) 0.027(11) Uiso 1 1 d . . . . .
H1B H 0.253(3) 0.752(3) 0.398(3) 0.008(8) Uiso 1 1 d . . . . .
N2 N 0.3080(2) 1.0815(2) 0.5058(2) 0.0185(5) Uani 1 1 d . . . . .
H2A H 0.363(3) 1.123(4) 0.475(3) 0.016(9) Uiso 1 1 d . . . . .
H2B H 0.226(4) 1.114(4) 0.478(4) 0.033(12) Uiso 1 1 d . . . . .
C1 C 0.2792(2) 0.5853(2) 0.2511(2) 0.0128(5) Uani 1 1 d D U . . .
C2 C 0.2945(2) 0.5210(3) 0.1619(2) 0.0151(5) Uani 1 1 d . U . . .
H2 H 0.3006 0.5642 0.1005 0.018 Uiso 1 1 calc R . . . .
C3 C 0.3008(3) 0.3968(3) 0.1621(2) 0.0161(5) Uani 1 1 d D U . . .
C7 C 0.2956(2) 0.9151(2) 0.3781(2) 0.0116(5) Uani 1 1 d . . . . .
H7A H 0.2199 0.9460 0.3472 0.014 Uiso 1 1 calc R . . . .
H7B H 0.3551 0.9541 0.3423 0.014 Uiso 1 1 calc R . . . .
C8 C 0.3148(3) 0.9501(2) 0.4904(2) 0.0142(5) Uani 1 1 d . . . . .
H8A H 0.2565 0.9094 0.5264 0.017 Uiso 1 1 calc R . . . .
H8B H 0.3913 0.9209 0.5208 0.017 Uiso 1 1 calc R . . . .
C9 C 0.1412(2) 0.7765(3) 0.2021(2) 0.0139(5) Uani 1 1 d . . . . .
C10 C 0.0468(3) 0.6997(3) 0.2025(2) 0.0201(6) Uani 1 1 d . . . . .
H10 H 0.0583 0.6177 0.2232 0.024 Uiso 1 1 calc R . . . .
C11 C -0.0633(3) 0.7419(4) 0.1731(3) 0.0287(8) Uani 1 1 d . . . . .
C12 C -0.0842(3) 0.8592(4) 0.1434(3) 0.0327(9) Uani 1 1 d . . . . .
C13 C 0.0080(3) 0.9355(4) 0.1401(3) 0.0286(8) Uani 1 1 d . . . . .
C14 C 0.1191(3) 0.8964(3) 0.1680(2) 0.0185(6) Uani 1 1 d . . . . .
H14 H 0.1813 0.9506 0.1642 0.022 Uiso 1 1 calc R . . . .
B1 B 0.2710(3) 0.7326(3) 0.2447(2) 0.0114(5) Uani 1 1 d . . . . .
F2A F 0.2868(19) 0.2065(11) 0.249(3) 0.031(3) Uani 0.578(8) 1 d D U P D 1
F3A F 0.2424(7) 0.3258(5) 0.4175(4) 0.0411(14) Uani 0.578(8) 1 d D U P D 1
C4A C 0.2808(5) 0.3288(6) 0.2467(5) 0.0166(8) Uiso 0.578(8) 1 d D U P D 1
C5A C 0.2613(9) 0.3912(9) 0.3339(8) 0.023(2) Uani 0.578(8) 1 d D U P D 1
C6A C 0.2567(5) 0.5163(5) 0.3358(4) 0.0135(8) Uiso 0.578(8) 1 d D U P D 1
H6A H 0.2370 0.5563 0.3949 0.016 Uiso 0.578(8) 1 d R . P D 1
F2B F 0.312(3) 0.2100(16) 0.246(4) 0.031(3) Uani 0.422(8) 1 d D U P D 2
F3B F 0.3051(10) 0.3288(7) 0.4264(6) 0.0411(14) Uani 0.422(8) 1 d D U P D 2
C4B C 0.3063(8) 0.3318(8) 0.2494(7) 0.0166(8) Uiso 0.422(8) 1 d D U P D 2
C5B C 0.2975(14) 0.3943(12) 0.3380(11) 0.023(2) Uani 0.422(8) 1 d D U P D 2
C6B C 0.2917(8) 0.5178(7) 0.3424(6) 0.0135(8) Uiso 0.422(8) 1 d D U P D 2
H6B H 0.2916 0.5580 0.4061 0.016 Uiso 0.422(8) 1 d R . P D 2
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
Cl7 0.041(5) 0.030(4) 0.32(3) 0.010(8) 0.073(10) -0.010(4)
Cl8 0.107(8) 0.068(6) 0.044(4) 0.024(4) 0.020(5) 0.063(6)
C2S 0.049(3) 0.044(3) 0.055(3) -0.001(2) 0.006(3) -0.010(2)
C1S 0.049(3) 0.044(3) 0.055(3) -0.001(2) 0.006(3) -0.010(2)
Cl1 0.116(2) 0.100(2) 0.0861(16) 0.0565(15) -0.0208(17) -0.0567(19)
Cl2 0.0445(11) 0.091(2) 0.113(2) -0.0112(15) 0.0096(11) -0.0200(12)
Cl3 0.0903(16) 0.0470(9) 0.0625(12) -0.0036(9) -0.0085(11) 0.0071(10)
Cl4 0.026(3) 0.039(4) 0.070(5) 0.017(3) 0.017(3) -0.014(3)
F7 0.0639(15) 0.0146(8) 0.0147(9) 0.0047(7) -0.0012(9) -0.0007(9)
F8 0.0476(13) 0.0105(8) 0.0275(10) -0.0021(7) -0.0019(9) 0.0042(8)
F9 0.0394(12) 0.0194(9) 0.0156(9) -0.0093(7) -0.0005(8) 0.0057(8)
F10 0.0155(9) 0.0744(18) 0.0358(12) -0.0124(12) 0.0070(8) -0.0173(11)
F11 0.0144(10) 0.105(2) 0.0362(13) 0.0094(14) 0.0003(9) 0.0208(12)
F12 0.0410(13) 0.0580(16) 0.0437(14) 0.0238(12) 0.0063(11) 0.0326(12)
O2 0.0136(9) 0.0161(9) 0.0124(9) 0.0053(8) 0.0015(7) -0.0002(7)
N3 0.0110(10) 0.0102(10) 0.0106(10) -0.0010(8) 0.0014(8) 0.0001(8)
N4 0.0254(14) 0.0141(11) 0.0202(13) -0.0043(10) 0.0061(11) -0.0046(10)
C15 0.0107(11) 0.0110(11) 0.0126(12) -0.0002(9) 0.0016(9) -0.0015(9)
C16 0.0234(14) 0.0122(12) 0.0119(12) -0.0027(9) 0.0016(10) -0.0027(10)
C17 0.0282(15) 0.0148(13) 0.0122(13) 0.0039(10) -0.0005(11) -0.0015(11)
C18 0.0241(15) 0.0096(11) 0.0210(14) -0.0032(10) -0.0001(11) 0.0007(10)
C19 0.0183(13) 0.0175(13) 0.0120(13) -0.0068(10) 0.0000(10) 0.0005(10)
C20 0.0132(12) 0.0154(12) 0.0114(12) 0.0002(10) -0.0002(9) 0.0013(10)
C21 0.0117(11) 0.0176(13) 0.0112(12) -0.0025(10) 0.0011(9) 0.0015(10)
C22 0.0132(13) 0.0273(15) 0.0164(14) -0.0055(11) 0.0022(10) -0.0030(11)
C23 0.0138(13) 0.049(2) 0.0183(15) -0.0088(14) 0.0051(11) -0.0051(14)
C24 0.0121(13) 0.068(3) 0.0192(15) -0.0020(16) -0.0010(11) 0.0111(15)
C25 0.0257(16) 0.047(2) 0.0184(15) 0.0099(14) 0.0043(12) 0.0194(15)
C26 0.0192(14) 0.0266(15) 0.0150(13) 0.0029(11) 0.0041(10) 0.0080(12)
C27 0.0182(13) 0.0107(12) 0.0136(13) -0.0016(9) 0.0032(10) 0.0001(10)
C28 0.0191(13) 0.0130(12) 0.0131(13) -0.0034(10) 0.0028(10) -0.0017(10)
B2 0.0125(13) 0.0093(12) 0.0094(13) 0.0005(10) 0.0010(10) 0.0003(10)
F1 0.0340(11) 0.0228(9) 0.0185(9) -0.0102(7) 0.0030(8) 0.0046(8)
F4 0.0135(9) 0.0705(18) 0.0486(15) -0.0244(13) 0.0065(9) -0.0152(10)
F5 0.0193(10) 0.097(2) 0.0382(13) -0.0073(13) -0.0069(9) 0.0273(13)
F6 0.0503(14) 0.0479(14) 0.0359(13) 0.0204(11) 0.0053(10) 0.0334(12)
O1 0.0110(9) 0.0155(9) 0.0126(9) 0.0047(7) 0.0012(7) 0.0006(7)
N1 0.0129(11) 0.0097(10) 0.0103(11) 0.0002(8) 0.0017(9) -0.0005(8)
N2 0.0258(14) 0.0131(11) 0.0175(12) -0.0041(9) 0.0067(10) -0.0025(10)
C1 0.0144(12) 0.0117(12) 0.0122(12) -0.0006(10) 0.0012(9) 0.0009(9)
C2 0.0156(13) 0.0152(13) 0.0146(13) -0.0011(10) 0.0019(10) 0.0001(10)
C3 0.0155(13) 0.0163(13) 0.0158(13) -0.0073(10) -0.0007(10) 0.0007(10)
C7 0.0152(12) 0.0083(11) 0.0110(12) -0.0006(9) 0.0009(9) -0.0002(9)
C8 0.0181(13) 0.0124(12) 0.0121(12) -0.0012(10) 0.0024(10) 0.0004(10)
C9 0.0130(12) 0.0191(13) 0.0093(12) -0.0015(10) 0.0002(9) 0.0012(10)
C10 0.0168(13) 0.0258(15) 0.0179(14) -0.0069(11) 0.0032(11) -0.0032(11)
C11 0.0104(13) 0.054(2) 0.0222(16) -0.0139(15) 0.0026(11) -0.0056(14)
C12 0.0160(15) 0.063(3) 0.0181(15) -0.0062(15) -0.0018(12) 0.0158(15)
C13 0.0287(17) 0.041(2) 0.0164(14) 0.0072(13) 0.0026(12) 0.0204(15)
C14 0.0189(14) 0.0240(14) 0.0125(13) 0.0041(11) 0.0017(10) 0.0061(11)
B1 0.0114(13) 0.0113(12) 0.0112(13) -0.0011(10) -0.0003(10) 0.0004(10)
F2A 0.051(10) 0.0085(10) 0.035(2) -0.0023(13) 0.011(7) 0.001(3)
F3A 0.088(4) 0.0140(11) 0.0251(16) 0.0073(10) 0.021(3) 0.001(3)
C5A 0.042(7) 0.0119(15) 0.0182(18) 0.0033(13) 0.010(3) -0.002(3)
F2B 0.051(10) 0.0085(10) 0.035(2) -0.0023(13) 0.011(7) 0.001(3)
F3B 0.088(4) 0.0140(11) 0.0251(16) 0.0073(10) 0.021(3) 0.001(3)
C5B 0.042(7) 0.0119(15) 0.0182(18) 0.0033(13) 0.010(3) -0.002(3)
_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
Cl6 C2S 1.796(19) . ?
Cl7 C2S 1.732(18) . ?
Cl8 C2S 1.805(18) . ?
C1S Cl1 1.731(6) . ?
C1S Cl2 1.795(6) . ?
C1S Cl3 1.704(6) . ?
C1S Cl4 1.708(8) . ?
C1S Cl5 1.873(10) . ?
F7 C17 1.356(3) . ?
F8 C18 1.351(3) . ?
F9 C19 1.356(3) . ?
F10 C23 1.354(4) . ?
F11 C24 1.347(4) . ?
F12 C25 1.354(4) . ?
O2 B2 1.451(4) . ?
N3 C27 1.489(3) . ?
N3 B2 1.635(4) . ?
N4 C28 1.466(4) . ?
C15 C16 1.402(4) . ?
C15 C20 1.398(4) . ?
C15 B2 1.631(4) . ?
C16 C17 1.382(4) . ?
C17 C18 1.370(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.379(4) . ?
C21 C22 1.404(4) . ?
C21 C26 1.398(4) . ?
C21 B2 1.630(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.357(6) . ?
C24 C25 1.369(6) . ?
C25 C26 1.388(4) . ?
C27 C28 1.531(4) . ?
F1 C3 1.355(3) . ?
F4 C11 1.356(4) . ?
F5 C12 1.347(4) . ?
F6 C13 1.354(4) . ?
O1 B1 1.447(4) . ?
N1 C7 1.483(3) . ?
N1 B1 1.645(4) . ?
N2 C8 1.467(4) . ?
C1 C2 1.406(4) . ?
C1 B1 1.629(4) . ?
C1 C6A 1.404(6) . ?
C1 C6B 1.408(8) . ?
C2 C3 1.371(4) . ?
C3 C4A 1.389(7) . ?
C3 C4B 1.351(9) . ?
C7 C8 1.521(4) . ?
C9 C10 1.396(4) . ?
C9 C14 1.410(4) . ?
C9 B1 1.630(4) . ?
C10 C11 1.383(5) . ?
C11 C12 1.365(6) . ?
C12 C13 1.376(6) . ?
C13 C14 1.380(4) . ?
F2A C4A 1.351(12) . ?
F3A C5A 1.360(9) . ?
C4A C5A 1.385(10) . ?
C5A C6A 1.381(10) . ?
F2B C4B 1.345(17) . ?
F3B C5B 1.365(14) . ?
C4B C5B 1.373(15) . ?
C5B C6B 1.364(14) . ?
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
Cl6 C2S Cl8 111.1(12) . . ?
Cl7 C2S Cl6 102.9(12) . . ?
Cl7 C2S Cl8 124.1(17) . . ?
Cl1 C1S Cl2 106.7(4) . . ?
Cl3 C1S Cl1 118.6(4) . . ?
Cl3 C1S Cl2 109.2(3) . . ?
Cl4 C1S Cl5 104.5(5) . . ?
C27 N3 B2 116.1(2) . . ?
C16 C15 B2 124.8(2) . . ?
C20 C15 C16 117.6(2) . . ?
C20 C15 B2 117.6(2) . . ?
C17 C16 C15 120.2(3) . . ?
F7 C17 C16 119.9(3) . . ?
F7 C17 C18 118.1(3) . . ?
C18 C17 C16 122.0(3) . . ?
F8 C18 C17 121.4(3) . . ?
F8 C18 C19 120.7(3) . . ?
C17 C18 C19 118.0(3) . . ?
F9 C19 C18 117.3(3) . . ?
F9 C19 C20 121.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C19 C20 C15 120.5(3) . . ?
C22 C21 B2 120.4(3) . . ?
C26 C21 C22 117.5(3) . . ?
C26 C21 B2 122.1(3) . . ?
C23 C22 C21 120.3(3) . . ?
F10 C23 C22 119.9(4) . . ?
F10 C23 C24 118.2(3) . . ?
C24 C23 C22 121.9(3) . . ?
F11 C24 C23 120.3(4) . . ?
F11 C24 C25 121.1(4) . . ?
C23 C24 C25 118.5(3) . . ?
F12 C25 C24 118.1(3) . . ?
F12 C25 C26 120.2(4) . . ?
C24 C25 C26 121.7(3) . . ?
C25 C26 C21 120.1(3) . . ?
N3 C27 C28 111.8(2) . . ?
N4 C28 C27 112.9(2) . . ?
O2 B2 N3 105.7(2) . . ?
O2 B2 C15 110.6(2) . . ?
O2 B2 C21 115.4(2) . . ?
C15 B2 N3 106.5(2) . . ?
C21 B2 N3 107.6(2) . . ?
C21 B2 C15 110.5(2) . . ?
C7 N1 B1 116.8(2) . . ?
C2 C1 B1 118.2(2) . . ?
C2 C1 C6B 116.1(4) . . ?
C6A C1 C2 116.8(3) . . ?
C6A C1 B1 124.5(3) . . ?
C6B C1 B1 124.8(4) . . ?
C3 C2 C1 120.9(3) . . ?
F1 C3 C2 120.5(3) . . ?
F1 C3 C4A 117.6(4) . . ?
C2 C3 C4A 121.8(4) . . ?
C4B C3 F1 116.8(5) . . ?
C4B C3 C2 121.9(5) . . ?
N1 C7 C8 112.3(2) . . ?
N2 C8 C7 112.4(2) . . ?
C10 C9 C14 117.1(3) . . ?
C10 C9 B1 121.9(3) . . ?
C14 C9 B1 120.9(3) . . ?
C11 C10 C9 120.7(3) . . ?
F4 C11 C10 120.2(4) . . ?
F4 C11 C12 118.0(3) . . ?
C12 C11 C10 121.8(3) . . ?
F5 C12 C11 120.5(4) . . ?
F5 C12 C13 121.1(4) . . ?
C11 C12 C13 118.4(3) . . ?
F6 C13 C12 118.5(3) . . ?
F6 C13 C14 120.0(4) . . ?
C12 C13 C14 121.4(3) . . ?
C13 C14 C9 120.5(3) . . ?
O1 B1 N1 105.8(2) . . ?
O1 B1 C1 111.1(2) . . ?
O1 B1 C9 114.9(2) . . ?
C1 B1 N1 106.1(2) . . ?
C1 B1 C9 111.1(2) . . ?
C9 B1 N1 107.3(2) . . ?
F2A C4A C3 122.8(15) . . ?
F2A C4A C5A 119.5(16) . . ?
C5A C4A C3 117.6(6) . . ?
F3A C5A C4A 118.2(8) . . ?
F3A C5A C6A 120.3(8) . . ?
C6A C5A C4A 121.4(8) . . ?
C5A C6A C1 121.0(5) . . ?
C3 C4B C5B 117.3(9) . . ?
F2B C4B C3 120(2) . . ?
F2B C4B C5B 123(2) . . ?
F3B C5B C4B 117.2(11) . . ?
C6B C5B F3B 119.3(11) . . ?
C6B C5B C4B 123.2(11) . . ?
C5B C6B C1 119.4(8) . . ?
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
C1S D1 F12 1.00 2.37 3.185(7) 138.1 1_455
O2 H2C N4 0.75(5) 2.17(5) 2.900(3) 164(4) 2_565
N3 H3A O1 0.87(3) 1.99(3) 2.830(3) 162(3) .
N4 H4B F7 0.80(6) 2.38(6) 2.958(3) 130(5) 1_545
O1 H1 N2 0.93(5) 1.94(5) 2.862(3) 170(5) 2_574
N1 H1A O2 0.89(5) 1.97(5) 2.852(3) 173(4) .
N1 H1B F1 0.83(4) 2.58(4) 3.089(3) 121(3) 2_565
C7 H7A F10 0.99 2.53 3.167(3) 122.2 1_455
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.61(10)
2 0.39(10)
_iucr_refine_instructions_details
;
15srv104.res created by SHELXL-2014/7
TITL 15srv104 in Pc #7
REM reset to Pc #7
CELL 0.71073 11.75 11.0269 13.1973 90 97.3307 90
ZERR 4 0.0005 0.0004 0.0005 0 0.0014 0
LATT -1
SYMM +X,-Y,0.5+Z
SFAC C H B Cl D F N O
UNIT 58 52 4 6 2 24 8 4
EQIV $1 +X,2-Y,-0.5+Z
EQIV $2 +X,1-Y,0.5+Z
EQIV $3 +X,-1+Y,+Z
EQIV $4 -1+X,+Y,+Z
SADI C6A C1 C6B C1
SADI C4A C3 C4B C3
SADI F2A C4A F2B C4B
SADI Cl4 C1S Cl2 C1S Cl3 C1S Cl5 C1S Cl1 C1S Cl8 C2S Cl6 C2S Cl7 C2S
SADI C6A C5A C6B C5B
SADI C5A C4A C5B C4B
SADI F3A C5A F3B C5B
RIGU F1 C1 C2 C3 F2A > C6B
EADP C6A C6B
EADP C4B C4A
EADP F2A F2B
EADP F3A F3B
EADP C2S C1S
EADP C5B C5A
L.S. 7
PLAN 7
SIZE 0.274 0.336 0.481
TEMP -153.15
HTAB O1 N2_$1
HTAB N1 O2
HTAB O2 N4_$2
HTAB N3 O1
HTAB N1 F1_$2
HTAB N4 F7_$3
HTAB C1S F12_$4
HTAB C7 F10_$4
FREE Cl8 C1S
FREE Cl7 C1S
FREE C2S C1S
FREE Cl6 C1S
BIND Cl4 C1S
BOND
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM
REM
REM
WGHT 0.077000 0.770000
BASF 0.38902
FVAR 0.12600 0.57834
PART 3
CL6 4 -0.083823 0.396435 0.250124 10.15000 0.04748
CL7 4 -0.178016 0.170153 0.272229 10.15000 0.04142 0.02975 =
0.31807 0.00973 0.07306 -0.01012
CL8 4 0.043467 0.247281 0.414348 10.15000 0.10669 0.06817 =
0.04436 0.02417 0.02041 0.06307
C2S 1 -0.047643 0.245233 0.293425 10.15000 0.04861 0.04445 =
0.05541 -0.00112 0.00552 -0.01025
AFIX 3
D2 5 -0.000563 0.211893 0.241915 10.15000 -1.20000
AFIX 0
PART 0
C1S 1 -0.048263 0.288019 0.363046 10.85000 0.04861 0.04445 =
0.05541 -0.00112 0.00552 -0.01025
PART 1
AFIX 3
D1 5 -0.015873 0.332959 0.425996 10.85000 -1.20000
AFIX 0
CL1 4 -0.042925 0.371564 0.252705 10.85000 0.11619 0.10016 =
0.08610 0.05647 -0.02081 -0.05670
CL2 4 -0.193600 0.295492 0.391084 10.70000 0.04455 0.09142 =
0.11327 -0.01119 0.00960 -0.02000
CL3 4 -0.005243 0.140335 0.364948 10.70000 0.09025 0.04701 =
0.06246 -0.00362 -0.00846 0.00714
PART 0
PART 2
CL4 4 -0.168782 0.207378 0.378970 10.15000 0.02637 0.03913 =
0.06960 0.01750 0.01651 -0.01425
CL5 4 0.052529 0.172699 0.320288 10.15000 0.05721
PART 0
F7 6 0.534018 1.169084 0.175005 11.00000 0.06391 0.01462 =
0.01468 0.00466 -0.00120 -0.00066
F8 6 0.540581 1.290594 0.354339 11.00000 0.04759 0.01048 =
0.02747 -0.00208 -0.00187 0.00419
F9 6 0.582673 1.169518 0.531955 11.00000 0.03943 0.01936 =
0.01565 -0.00933 -0.00046 0.00570
F10 6 1.034795 0.881119 0.409800 11.00000 0.01546 0.07439 =
0.03576 -0.01241 0.00701 -0.01734
F11 6 1.095999 0.667081 0.495717 11.00000 0.01440 0.10516 =
0.03623 0.00942 0.00031 0.02084
F12 6 0.934088 0.500573 0.523713 11.00000 0.04101 0.05797 =
0.04373 0.02379 0.00626 0.03256
O2 8 0.533785 0.714416 0.416933 11.00000 0.01364 0.01607 =
0.01236 0.00534 0.00153 -0.00016
H2C 2 0.559090 0.675312 0.460979 11.00000 -1.20000
N3 7 0.593213 0.719040 0.244697 11.00000 0.01102 0.01025 =
0.01058 -0.00102 0.00140 0.00012
H3A 2 0.526344 0.743415 0.215440 11.00000 0.00187
H3B 2 0.654997 0.764413 0.202378 11.00000 0.03465
N4 7 0.592422 0.414782 0.107834 11.00000 0.02538 0.01407 =
0.02024 -0.00433 0.00610 -0.00456
H4A 2 0.662451 0.394345 0.137733 11.00000 0.02687
H4B 2 0.545097 0.378879 0.135221 11.00000 0.05068
C15 1 0.596885 0.917778 0.353547 11.00000 0.01068 0.01101 =
0.01264 -0.00024 0.00165 -0.00152
C16 1 0.574698 0.982980 0.261977 11.00000 0.02337 0.01219 =
0.01193 -0.00267 0.00163 -0.00271
AFIX 43
H16 2 0.572345 0.942007 0.198421 11.00000 -1.20000
AFIX 0
C17 1 0.556237 1.106685 0.263878 11.00000 0.02821 0.01480 =
0.01219 0.00392 -0.00052 -0.00147
C18 1 0.558740 1.169664 0.353622 11.00000 0.02414 0.00963 =
0.02104 -0.00324 -0.00014 0.00071
C19 1 0.581403 1.106051 0.443802 11.00000 0.01827 0.01747 =
0.01197 -0.00679 0.00004 0.00052
C20 1 0.600345 0.982580 0.444970 11.00000 0.01316 0.01535 =
0.01139 0.00019 -0.00018 0.00130
AFIX 43
H20 2 0.615864 0.941239 0.508384 11.00000 -1.20000
AFIX 0
C21 1 0.751600 0.742284 0.403678 11.00000 0.01166 0.01760 =
0.01121 -0.00250 0.00110 0.00149
C22 1 0.837874 0.827093 0.391441 11.00000 0.01317 0.02733 =
0.01641 -0.00548 0.00223 -0.00301
AFIX 43
H22 2 0.817973 0.903833 0.361584 11.00000 -1.20000
AFIX 0
C23 1 0.951969 0.799323 0.422739 11.00000 0.01384 0.04938 =
0.01832 -0.00883 0.00513 -0.00507
C24 1 0.984239 0.691236 0.466460 11.00000 0.01208 0.06834 =
0.01921 -0.00198 -0.00105 0.01109
C25 1 0.900979 0.608101 0.479877 11.00000 0.02565 0.04720 =
0.01836 0.00990 0.00433 0.01938
C26 1 0.785660 0.631207 0.448896 11.00000 0.01917 0.02662 =
0.01503 0.00289 0.00409 0.00801
AFIX 43
H26 2 0.729765 0.571447 0.458430 11.00000 -1.20000
AFIX 0
C27 1 0.601850 0.585129 0.233448 11.00000 0.01820 0.01071 =
0.01360 -0.00159 0.00321 0.00011
AFIX 23
H27A 2 0.542110 0.545493 0.268467 11.00000 -1.20000
H27B 2 0.677664 0.557491 0.266798 11.00000 -1.20000
AFIX 0
C28 1 0.587032 0.546610 0.121091 11.00000 0.01912 0.01302 =
0.01314 -0.00337 0.00285 -0.00171
AFIX 23
H28A 2 0.512094 0.576453 0.087548 11.00000 -1.20000
H28B 2 0.647870 0.585108 0.086694 11.00000 -1.20000
AFIX 0
B2 3 0.618095 0.771679 0.361209 11.00000 0.01253 0.00926 =
0.00940 0.00045 0.00103 0.00028
F1 6 0.319526 0.335888 0.076653 11.00000 0.03395 0.02284 =
0.01852 -0.01024 0.00300 0.00460
F4 6 -0.154547 0.667303 0.176263 11.00000 0.01352 0.07053 =
0.04865 -0.02444 0.00654 -0.01518
F5 6 -0.192544 0.898740 0.117798 11.00000 0.01930 0.09686 =
0.03817 -0.00733 -0.00689 0.02725
F6 6 -0.012421 1.052077 0.110938 11.00000 0.05034 0.04794 =
0.03585 0.02038 0.00531 0.03345
O1 8 0.359983 0.782121 0.190337 11.00000 0.01104 0.01548 =
0.01259 0.00466 0.00123 0.00063
H1 2 0.336055 0.829814 0.133863 11.00000 0.03215
N1 7 0.299640 0.782000 0.362769 11.00000 0.01286 0.00971 =
0.01031 0.00022 0.00171 -0.00055
H1A 2 0.370196 0.755528 0.382657 11.00000 0.02715
H1B 2 0.252924 0.752092 0.397736 11.00000 0.00821
N2 7 0.307965 1.081484 0.505771 11.00000 0.02579 0.01310 =
0.01747 -0.00414 0.00665 -0.00249
H2A 2 0.362542 1.123480 0.474782 11.00000 0.01602
H2B 2 0.226468 1.114338 0.478259 11.00000 0.03311
C1 1 0.279234 0.585280 0.251129 11.00000 0.01443 0.01172 =
0.01225 -0.00062 0.00115 0.00091
C2 1 0.294509 0.520977 0.161865 11.00000 0.01559 0.01518 =
0.01463 -0.00111 0.00189 0.00014
AFIX 43
H2 2 0.300567 0.564161 0.100495 11.00000 -1.20000
AFIX 0
C3 1 0.300785 0.396796 0.162148 11.00000 0.01553 0.01628 =
0.01580 -0.00734 -0.00074 0.00073
C7 1 0.295568 0.915084 0.378052 11.00000 0.01523 0.00832 =
0.01097 -0.00059 0.00093 -0.00022
AFIX 23
H7A 2 0.219903 0.946006 0.347200 11.00000 -1.20000
H7B 2 0.355097 0.954052 0.342342 11.00000 -1.20000
AFIX 0
C8 1 0.314829 0.950053 0.490399 11.00000 0.01812 0.01237 =
0.01214 -0.00115 0.00236 0.00038
AFIX 23
H8A 2 0.256511 0.909378 0.526437 11.00000 -1.20000
H8B 2 0.391327 0.920929 0.520812 11.00000 -1.20000
AFIX 0
C9 1 0.141239 0.776469 0.202081 11.00000 0.01296 0.01913 =
0.00926 -0.00149 0.00015 0.00118
C10 1 0.046817 0.699741 0.202521 11.00000 0.01680 0.02580 =
0.01790 -0.00692 0.00317 -0.00319
AFIX 43
H10 2 0.058325 0.617671 0.223225 11.00000 -1.20000
AFIX 0
C11 1 -0.063301 0.741894 0.173143 11.00000 0.01044 0.05360 =
0.02224 -0.01395 0.00262 -0.00565
C12 1 -0.084185 0.859245 0.143385 11.00000 0.01598 0.06311 =
0.01812 -0.00618 -0.00180 0.01584
C13 1 0.007975 0.935549 0.140111 11.00000 0.02866 0.04067 =
0.01641 0.00725 0.00259 0.02043
C14 1 0.119138 0.896369 0.168019 11.00000 0.01887 0.02398 =
0.01248 0.00415 0.00173 0.00612
AFIX 43
H14 2 0.181251 0.950636 0.164242 11.00000 -1.20000
AFIX 0
B1 3 0.271045 0.732624 0.244656 11.00000 0.01140 0.01125 =
0.01117 -0.00107 -0.00026 0.00042
PART 1
F2A 6 0.286817 0.206533 0.248781 21.00000 0.05091 0.00853 =
0.03549 -0.00226 0.01143 0.00146
F3A 6 0.242411 0.325794 0.417533 21.00000 0.08768 0.01400 =
0.02511 0.00726 0.02078 0.00056
C4A 1 0.280778 0.328831 0.246672 21.00000 0.01657
C5A 1 0.261314 0.391200 0.333945 21.00000 0.04169 0.01185 =
0.01823 0.00328 0.01022 -0.00205
C6A 1 0.256706 0.516329 0.335764 21.00000 0.01347
AFIX 3
H6A 2 0.237016 0.556339 0.394854 21.00000 -1.20000
AFIX 0
PART 0
PART 2
F2B 6 0.311799 0.210019 0.245971 -21.00000 0.05091 0.00853 =
0.03549 -0.00226 0.01143 0.00146
F3B 6 0.305096 0.328768 0.426360 -21.00000 0.08768 0.01400 =
0.02511 0.00726 0.02078 0.00056
C4B 1 0.306330 0.331796 0.249416 -21.00000 0.01657
C5B 1 0.297540 0.394339 0.338003 -21.00000 0.04169 0.01185 =
0.01823 0.00328 0.01022 -0.00205
C6B 1 0.291717 0.517762 0.342414 -21.00000 0.01347
AFIX 3
H6B 2 0.291627 0.558032 0.406064 -21.00000 -1.20000
AFIX 0
HKLF 4
REM 15srv104 in Pc #7
REM R1 = 0.0459 for 8294 Fo > 4sig(Fo) and 0.0535 for all 9254 data
REM 553 parameters refined using 57 restraints
END
WGHT 0.0773 0.7684
REM Highest difference peak 0.501, deepest hole -0.634, 1-sigma level 0.064
Q1 1 -0.1859 0.2195 0.2006 11.00000 0.05 0.50
Q2 1 -0.1561 0.1617 0.3857 11.00000 0.05 0.42
Q3 1 -0.1821 0.2144 0.3221 11.00000 0.05 0.39
Q4 1 0.0624 0.2815 0.4127 11.00000 0.05 0.38
Q5 1 -0.0215 0.2185 0.4082 11.00000 0.05 0.38
Q6 1 -0.1788 0.3227 0.3260 11.00000 0.05 0.37
Q7 1 0.0728 0.2524 0.4278 11.00000 0.05 0.37
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_10a_15srv091
_database_code_depnum_ccdc_archive 'CCDC 1551620'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2015-03-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic
' 3,4,5-Trifluorophenylboroxine -- benzylamine complex '
_chemical_formula_moiety 'C25 H15 B3 F9 N O3'
_chemical_formula_sum 'C25 H15 B3 F9 N O3'
_chemical_formula_weight 580.81
_chemical_melting_point 479(1)
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.3720(5)
_cell_length_b 11.1795(5)
_cell_length_c 12.3123(6)
_cell_angle_alpha 106.5448(14)
_cell_angle_beta 111.4917(14)
_cell_angle_gamma 96.8493(15)
_cell_volume 1232.74(10)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9217
_cell_measurement_temperature 120
_cell_measurement_theta_max 30.12
_cell_measurement_theta_min 2.54
_shelx_estimated_absorpt_T_max 0.971
_shelx_estimated_absorpt_T_min 0.953
_exptl_absorpt_coefficient_mu 0.146
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9701
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.9701.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.565
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0990
0.00 0.00 1.00 0.0850
-2.00 2.00 1.00 0.0840
0.00 1.00 -1.00 0.1000
0.00 -1.00 1.00 0.0880
1.00 1.00 -2.00 0.1080
1.00 0.00 -1.00 0.1050
-1.00 0.00 1.00 0.0920
-2.00 1.00 0.00 0.0990
2.00 -1.00 0.00 0.1180
2.00 -1.00 -1.00 0.1000
2.00 0.00 -1.00 0.1150
-2.00 2.00 -1.00 0.0870
0.00 -2.00 -1.00 0.1600
1.00 0.00 -2.00 0.0970
0.00 2.00 -1.00 0.1250
_exptl_crystal_size_max 0.332
_exptl_crystal_size_mid 0.224
_exptl_crystal_size_min 0.2
_exptl_special_details
;
Data collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of narrow-frame \w-scans (scan
width 0.5\%, 10s exposure), every run at a different \f angle.
One run of \f-scans (scan width 1\%, 1s exposure) was used for
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0242
_diffrn_reflns_av_unetI/netI 0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 27452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 30.000
_diffrn_reflns_theta_max 30.119
_diffrn_reflns_theta_min 2.180
_diffrn_ambient_temperature 120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'ImuS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6223
_reflns_number_total 7267
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.455
_refine_diff_density_min -0.217
_refine_diff_density_rms 0.049
_refine_ls_extinction_coef 0.0054(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 379
_refine_ls_number_reflns 7267
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0432
_refine_ls_R_factor_gt 0.0358
_refine_ls_restrained_S_all 1.034
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.4680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0954
_refine_ls_wR_factor_ref 0.1003
_refine_special_details
;
Amino H atoms - refall, other H atoms - riding model (constr)
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
C2(H2), C6(H6), C8(H8), C12(H12), C14(H14), C18(H18), C21(H21), C22(H22),
C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.05535(9) 0.30024(8) 0.74980(7) 0.03254(18) Uani 1 1 d . . . . .
F2 F 0.09409(8) 0.55845(7) 0.82722(6) 0.02758(16) Uani 1 1 d . . . . .
F3 F 0.18335(8) 0.69424(6) 0.70887(7) 0.02490(15) Uani 1 1 d . . . . .
F4 F 0.13661(8) 0.67065(7) 0.07296(7) 0.02614(16) Uani 1 1 d . . . . .
F5 F 0.37277(8) 0.71619(8) 0.02962(7) 0.03052(17) Uani 1 1 d . . . . .
F6 F 0.59218(8) 0.61493(9) 0.12185(8) 0.03329(19) Uani 1 1 d . . . . .
F7 F 0.82316(8) 0.06711(8) 0.36471(8) 0.03233(18) Uani 1 1 d . . . . .
F8 F 0.88830(7) 0.02064(7) 0.57816(8) 0.02930(17) Uani 1 1 d . . . . .
F9 F 0.73125(8) 0.07663(8) 0.71143(7) 0.03067(17) Uani 1 1 d . . . . .
O1 O 0.22367(8) 0.38538(7) 0.34033(7) 0.01451(14) Uani 1 1 d . . . . .
O2 O 0.44626(8) 0.34003(8) 0.35271(7) 0.01824(15) Uani 1 1 d . . . . .
O3 O 0.31740(7) 0.23529(7) 0.43992(7) 0.01471(14) Uani 1 1 d . . . . .
N N 0.06059(9) 0.18549(8) 0.30460(8) 0.01349(16) Uani 1 1 d . . . . .
H1N H 0.0485(16) 0.1287(15) 0.3366(14) 0.023(4) Uiso 1 1 d . . . . .
H2N H -0.0177(17) 0.2150(15) 0.2936(14) 0.027(4) Uiso 1 1 d . . . . .
C1 C 0.16869(10) 0.37038(9) 0.52173(9) 0.01341(17) Uani 1 1 d . . . . .
C2 C 0.12499(12) 0.30157(10) 0.58670(10) 0.01799(19) Uani 1 1 d . . . . .
H2 H 0.1132 0.2109 0.5611 0.022 Uiso 1 1 calc R . . . .
C3 C 0.09910(12) 0.36495(11) 0.68741(10) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.11813(11) 0.49692(11) 0.72839(10) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.16290(10) 0.56422(10) 0.66542(10) 0.01656(19) Uani 1 1 d . . . . .
C6 C 0.18674(10) 0.50397(10) 0.56273(9) 0.01490(18) Uani 1 1 d . . . . .
H6 H 0.2153 0.5529 0.5200 0.018 Uiso 1 1 calc R . . . .
C7 C 0.35077(10) 0.49021(9) 0.23885(9) 0.01433(18) Uani 1 1 d . . . . .
C8 C 0.23670(11) 0.54296(10) 0.18952(9) 0.01590(18) Uani 1 1 d . . . . .
H8 H 0.1536 0.5267 0.2040 0.019 Uiso 1 1 calc R . . . .
C9 C 0.24482(11) 0.61828(10) 0.12003(10) 0.01736(19) Uani 1 1 d . . . . .
C10 C 0.36477(12) 0.64300(11) 0.09740(10) 0.0198(2) Uani 1 1 d . . . . .
C11 C 0.47714(11) 0.59083(11) 0.14626(11) 0.0206(2) Uani 1 1 d . . . . .
C12 C 0.47210(11) 0.51531(10) 0.21628(10) 0.01772(19) Uani 1 1 d . . . . .
H12 H 0.5506 0.4804 0.2491 0.021 Uiso 1 1 calc R . . . .
C13 C 0.55568(10) 0.18973(9) 0.45864(9) 0.01515(18) Uani 1 1 d . . . . .
C14 C 0.63642(11) 0.15894(10) 0.39019(10) 0.0186(2) Uani 1 1 d . . . . .
H14 H 0.6165 0.1784 0.3164 0.022 Uiso 1 1 calc R . . . .
C15 C 0.74500(11) 0.10019(11) 0.43022(11) 0.0208(2) Uani 1 1 d . . . . .
C16 C 0.77825(11) 0.07390(10) 0.53888(11) 0.0203(2) Uani 1 1 d . . . . .
C17 C 0.69808(12) 0.10392(10) 0.60626(10) 0.0195(2) Uani 1 1 d . . . . .
C18 C 0.58654(11) 0.15995(10) 0.56692(10) 0.01720(19) Uani 1 1 d . . . . .
H18 H 0.5309 0.1783 0.6132 0.021 Uiso 1 1 calc R . . . .
C19 C 0.05553(11) 0.11908(10) 0.17833(9) 0.0183(2) Uani 1 1 d . . . . .
H19A H 0.1339 0.0748 0.1868 0.022 Uiso 1 1 calc R . . . .
H19B H 0.0692 0.1835 0.1400 0.022 Uiso 1 1 calc R . . . .
C20 C -0.08629(11) 0.02250(10) 0.09598(9) 0.01594(19) Uani 1 1 d . . . . .
C21 C -0.10510(13) -0.10401(11) 0.09277(10) 0.0213(2) Uani 1 1 d . . . . .
H21 H -0.0261 -0.1315 0.1384 0.026 Uiso 1 1 calc R . . . .
C22 C -0.23903(14) -0.19022(12) 0.02304(11) 0.0276(2) Uani 1 1 d . . . . .
H22 H -0.2516 -0.2764 0.0213 0.033 Uiso 1 1 calc R . . . .
C23 C -0.35430(13) -0.15041(13) -0.04392(12) 0.0310(3) Uani 1 1 d . . . . .
H23 H -0.4460 -0.2092 -0.0911 0.037 Uiso 1 1 calc R . . . .
C24 C -0.33588(13) -0.02495(13) -0.04208(12) 0.0310(3) Uani 1 1 d . . . . .
H24 H -0.4148 0.0021 -0.0884 0.037 Uiso 1 1 calc R . . . .
C25 C -0.20198(12) 0.06130(11) 0.02748(11) 0.0233(2) Uani 1 1 d . . . . .
H25 H -0.1895 0.1471 0.0282 0.028 Uiso 1 1 calc R . . . .
B1 B 0.20218(11) 0.29962(10) 0.40495(10) 0.01291(19) Uani 1 1 d . . . . .
B2 B 0.33838(12) 0.40152(10) 0.31451(10) 0.0143(2) Uani 1 1 d . . . . .
B3 B 0.43215(12) 0.25759(11) 0.41550(10) 0.0144(2) 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 0.0479(5) 0.0316(4) 0.0259(4) 0.0127(3) 0.0243(3) 0.0024(3)
F2 0.0257(3) 0.0330(4) 0.0212(3) -0.0004(3) 0.0153(3) 0.0044(3)
F3 0.0260(3) 0.0154(3) 0.0339(4) 0.0032(3) 0.0166(3) 0.0077(3)
F4 0.0275(3) 0.0338(4) 0.0302(4) 0.0221(3) 0.0143(3) 0.0199(3)
F5 0.0299(4) 0.0386(4) 0.0364(4) 0.0305(4) 0.0149(3) 0.0094(3)
F6 0.0178(3) 0.0540(5) 0.0430(4) 0.0340(4) 0.0166(3) 0.0076(3)
F7 0.0273(4) 0.0394(4) 0.0497(5) 0.0230(4) 0.0281(4) 0.0194(3)
F8 0.0182(3) 0.0253(3) 0.0463(4) 0.0196(3) 0.0082(3) 0.0125(3)
F9 0.0348(4) 0.0351(4) 0.0241(4) 0.0194(3) 0.0060(3) 0.0149(3)
O1 0.0149(3) 0.0153(3) 0.0176(3) 0.0092(3) 0.0082(3) 0.0060(3)
O2 0.0138(3) 0.0237(4) 0.0249(4) 0.0161(3) 0.0100(3) 0.0077(3)
O3 0.0134(3) 0.0167(3) 0.0181(3) 0.0098(3) 0.0074(3) 0.0065(3)
N 0.0136(4) 0.0147(4) 0.0138(4) 0.0053(3) 0.0072(3) 0.0043(3)
C1 0.0113(4) 0.0152(4) 0.0129(4) 0.0052(3) 0.0040(3) 0.0035(3)
C2 0.0222(5) 0.0160(4) 0.0164(4) 0.0062(4) 0.0088(4) 0.0036(4)
C3 0.0208(5) 0.0242(5) 0.0161(5) 0.0083(4) 0.0091(4) 0.0015(4)
C4 0.0141(4) 0.0247(5) 0.0143(4) 0.0024(4) 0.0068(4) 0.0042(4)
C5 0.0120(4) 0.0146(4) 0.0201(5) 0.0029(4) 0.0057(4) 0.0044(3)
C6 0.0117(4) 0.0161(4) 0.0178(4) 0.0070(4) 0.0059(3) 0.0049(3)
C7 0.0142(4) 0.0142(4) 0.0143(4) 0.0062(3) 0.0052(3) 0.0024(3)
C8 0.0157(4) 0.0177(4) 0.0168(4) 0.0077(4) 0.0080(4) 0.0051(4)
C9 0.0177(4) 0.0190(5) 0.0173(5) 0.0093(4) 0.0063(4) 0.0081(4)
C10 0.0214(5) 0.0211(5) 0.0194(5) 0.0129(4) 0.0076(4) 0.0034(4)
C11 0.0144(4) 0.0274(5) 0.0232(5) 0.0143(4) 0.0083(4) 0.0021(4)
C12 0.0132(4) 0.0219(5) 0.0197(5) 0.0114(4) 0.0058(4) 0.0039(4)
C13 0.0114(4) 0.0151(4) 0.0188(5) 0.0074(4) 0.0050(3) 0.0032(3)
C14 0.0155(4) 0.0211(5) 0.0240(5) 0.0123(4) 0.0097(4) 0.0065(4)
C15 0.0149(4) 0.0206(5) 0.0316(6) 0.0110(4) 0.0130(4) 0.0063(4)
C16 0.0127(4) 0.0153(4) 0.0310(6) 0.0109(4) 0.0045(4) 0.0054(4)
C17 0.0191(5) 0.0175(5) 0.0188(5) 0.0094(4) 0.0025(4) 0.0041(4)
C18 0.0164(4) 0.0165(4) 0.0179(5) 0.0068(4) 0.0057(4) 0.0044(4)
C19 0.0173(4) 0.0214(5) 0.0139(4) 0.0021(4) 0.0087(4) 0.0008(4)
C20 0.0174(4) 0.0177(4) 0.0124(4) 0.0038(3) 0.0075(4) 0.0029(4)
C21 0.0262(5) 0.0201(5) 0.0173(5) 0.0082(4) 0.0080(4) 0.0048(4)
C22 0.0353(6) 0.0208(5) 0.0226(5) 0.0066(4) 0.0116(5) -0.0030(5)
C23 0.0226(6) 0.0327(6) 0.0245(6) 0.0022(5) 0.0061(5) -0.0072(5)
C24 0.0195(5) 0.0351(7) 0.0279(6) 0.0065(5) 0.0023(4) 0.0066(5)
C25 0.0236(5) 0.0206(5) 0.0217(5) 0.0064(4) 0.0058(4) 0.0066(4)
B1 0.0126(4) 0.0135(4) 0.0145(5) 0.0063(4) 0.0063(4) 0.0041(4)
B2 0.0139(5) 0.0139(5) 0.0148(5) 0.0062(4) 0.0052(4) 0.0030(4)
B3 0.0127(4) 0.0151(5) 0.0155(5) 0.0066(4) 0.0050(4) 0.0041(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
F1 C3 1.3464(12) . ?
F2 C4 1.3425(12) . ?
F3 C5 1.3580(12) . ?
F4 C9 1.3460(12) . ?
F5 C10 1.3401(12) . ?
F6 C11 1.3486(12) . ?
F7 C15 1.3509(13) . ?
F8 C16 1.3464(11) . ?
F9 C17 1.3461(12) . ?
O1 B1 1.4544(12) . ?
O1 B2 1.3446(13) . ?
O2 B2 1.3885(13) . ?
O2 B3 1.3874(13) . ?
O3 B1 1.4612(12) . ?
O3 B3 1.3428(13) . ?
N C19 1.4982(13) . ?
N B1 1.6239(14) . ?
C1 C2 1.4036(14) . ?
C1 C6 1.3983(13) . ?
C1 B1 1.6117(14) . ?
C2 C3 1.3786(15) . ?
C3 C4 1.3798(16) . ?
C4 C5 1.3768(15) . ?
C5 C6 1.3774(14) . ?
C7 C8 1.4000(13) . ?
C7 C12 1.3986(14) . ?
C7 B2 1.5655(14) . ?
C8 C9 1.3764(14) . ?
C9 C10 1.3848(15) . ?
C10 C11 1.3815(15) . ?
C11 C12 1.3769(14) . ?
C13 C14 1.3968(14) . ?
C13 C18 1.3986(14) . ?
C13 B3 1.5690(14) . ?
C14 C15 1.3772(14) . ?
C15 C16 1.3803(16) . ?
C16 C17 1.3805(16) . ?
C17 C18 1.3785(14) . ?
C19 C20 1.5041(14) . ?
C20 C21 1.3917(15) . ?
C20 C25 1.3893(15) . ?
C21 C22 1.3897(16) . ?
C22 C23 1.3859(19) . ?
C23 C24 1.385(2) . ?
C24 C25 1.3895(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
B2 O1 B1 122.50(8) . . ?
B3 O2 B2 118.78(8) . . ?
B3 O3 B1 121.73(8) . . ?
C19 N B1 117.43(8) . . ?
C2 C1 B1 121.60(9) . . ?
C6 C1 C2 118.38(9) . . ?
C6 C1 B1 120.00(8) . . ?
C3 C2 C1 120.33(10) . . ?
F1 C3 C2 121.11(10) . . ?
F1 C3 C4 117.68(10) . . ?
C2 C3 C4 121.21(10) . . ?
F2 C4 C3 121.04(10) . . ?
F2 C4 C5 120.71(10) . . ?
C5 C4 C3 118.24(9) . . ?
F3 C5 C4 117.16(9) . . ?
F3 C5 C6 120.63(9) . . ?
C4 C5 C6 122.21(9) . . ?
C5 C6 C1 119.60(9) . . ?
C8 C7 B2 119.58(9) . . ?
C12 C7 C8 118.98(9) . . ?
C12 C7 B2 121.41(9) . . ?
C9 C8 C7 120.11(9) . . ?
F4 C9 C8 120.81(9) . . ?
F4 C9 C10 118.22(9) . . ?
C8 C9 C10 120.97(9) . . ?
F5 C10 C9 121.04(10) . . ?
F5 C10 C11 120.20(10) . . ?
C11 C10 C9 118.76(9) . . ?
F6 C11 C10 117.74(9) . . ?
F6 C11 C12 120.71(10) . . ?
C12 C11 C10 121.54(10) . . ?
C11 C12 C7 119.64(9) . . ?
C14 C13 C18 119.23(9) . . ?
C14 C13 B3 120.66(9) . . ?
C18 C13 B3 120.11(9) . . ?
C15 C14 C13 119.69(10) . . ?
F7 C15 C14 121.03(10) . . ?
F7 C15 C16 117.78(10) . . ?
C14 C15 C16 121.19(10) . . ?
F8 C16 C15 119.91(10) . . ?
F8 C16 C17 121.01(10) . . ?
C15 C16 C17 119.07(9) . . ?
F9 C17 C16 118.26(9) . . ?
F9 C17 C18 120.70(10) . . ?
C18 C17 C16 121.04(10) . . ?
C17 C18 C13 119.74(10) . . ?
N C19 C20 109.94(8) . . ?
C21 C20 C19 120.63(10) . . ?
C25 C20 C19 119.82(10) . . ?
C25 C20 C21 119.46(10) . . ?
C22 C21 C20 120.21(11) . . ?
C23 C22 C21 120.00(11) . . ?
C24 C23 C22 120.04(11) . . ?
C23 C24 C25 120.02(12) . . ?
C20 C25 C24 120.27(11) . . ?
O1 B1 O3 113.59(8) . . ?
O1 B1 N 105.84(8) . . ?
O1 B1 C1 111.96(8) . . ?
O3 B1 N 105.59(8) . . ?
O3 B1 C1 112.07(8) . . ?
C1 B1 N 107.18(7) . . ?
O1 B2 O2 121.31(9) . . ?
O1 B2 C7 119.71(9) . . ?
O2 B2 C7 118.98(9) . . ?
O2 B3 C13 118.00(9) . . ?
O3 B3 O2 122.03(9) . . ?
O3 B3 C13 119.97(9) . . ?
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
N H1N F7 0.857(16) 2.530(15) 3.0790(11) 122.7(12) 1_455
N H1N F8 0.857(16) 2.252(16) 3.0497(11) 154.9(14) 2_656
N H2N F3 0.892(16) 2.092(16) 2.9779(11) 172.0(14) 2_566
_shelx_SHELXL_version_number 2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
15srv091.res created by SHELXL-2014/7
TITL 15srv091 in P-1
CELL 0.71073 10.372 11.1795 12.3123 106.5448 111.4917 96.8493
ZERR 2 0.0005 0.0005 0.0006 0.0014 0.0014 0.0015
LATT 1
SFAC C H B N O F
UNIT 50 30 6 2 6 18
EQIV $1 -X,1-Y,1-Z
EQIV $2 -1+X,+Y,+Z
EQIV $3 1-X,-Y,1-Z
L.S. 7
PLAN 7
SIZE 0.2 0.224 0.332
TEMP -153.15
HTAB N F3_$1
HTAB N F7_$2
HTAB N F8_$3
BOND
fmap 2 53
acta 60
REM
REM
REM
WGHT 0.049000 0.468000
EXTI 0.005450
FVAR 0.19117
F1 6 0.055352 0.300240 0.749796 11.00000 0.04786 0.03161 =
0.02592 0.01269 0.02430 0.00235
F2 6 0.094093 0.558446 0.827216 11.00000 0.02572 0.03300 =
0.02118 -0.00039 0.01528 0.00440
F3 6 0.183350 0.694235 0.708870 11.00000 0.02602 0.01537 =
0.03391 0.00320 0.01665 0.00773
F4 6 0.136613 0.670652 0.072965 11.00000 0.02750 0.03379 =
0.03022 0.02210 0.01433 0.01989
F5 6 0.372768 0.716191 0.029624 11.00000 0.02987 0.03856 =
0.03635 0.03048 0.01485 0.00943
F6 6 0.592176 0.614935 0.121847 11.00000 0.01785 0.05395 =
0.04303 0.03395 0.01663 0.00756
F7 6 0.823155 0.067106 0.364714 11.00000 0.02728 0.03939 =
0.04967 0.02299 0.02811 0.01944
F8 6 0.888301 0.020643 0.578161 11.00000 0.01823 0.02529 =
0.04626 0.01965 0.00822 0.01246
F9 6 0.731248 0.076631 0.711432 11.00000 0.03484 0.03514 =
0.02409 0.01944 0.00602 0.01486
O1 5 0.223665 0.385377 0.340328 11.00000 0.01486 0.01534 =
0.01764 0.00921 0.00822 0.00605
O2 5 0.446265 0.340026 0.352713 11.00000 0.01383 0.02375 =
0.02495 0.01606 0.00999 0.00771
O3 5 0.317403 0.235291 0.439918 11.00000 0.01339 0.01672 =
0.01812 0.00982 0.00743 0.00649
N 4 0.060586 0.185495 0.304599 11.00000 0.01358 0.01475 =
0.01383 0.00529 0.00717 0.00431
H1N 2 0.048520 0.128663 0.336628 11.00000 0.02331
H2N 2 -0.017680 0.215019 0.293623 11.00000 0.02658
C1 1 0.168692 0.370380 0.521734 11.00000 0.01125 0.01524 =
0.01289 0.00521 0.00397 0.00351
C2 1 0.124985 0.301570 0.586698 11.00000 0.02223 0.01598 =
0.01640 0.00620 0.00882 0.00358
AFIX 43
H2 2 0.113181 0.210875 0.561144 11.00000 -1.20000
AFIX 0
C3 1 0.099100 0.364947 0.687408 11.00000 0.02079 0.02420 =
0.01615 0.00835 0.00907 0.00153
C4 1 0.118129 0.496922 0.728388 11.00000 0.01410 0.02467 =
0.01427 0.00244 0.00684 0.00420
C5 1 0.162897 0.564224 0.665420 11.00000 0.01197 0.01456 =
0.02015 0.00291 0.00567 0.00435
C6 1 0.186739 0.503972 0.562731 11.00000 0.01166 0.01612 =
0.01778 0.00704 0.00593 0.00489
AFIX 43
H6 2 0.215273 0.552889 0.520015 11.00000 -1.20000
AFIX 0
C7 1 0.350765 0.490210 0.238850 11.00000 0.01422 0.01420 =
0.01429 0.00616 0.00524 0.00238
C8 1 0.236704 0.542959 0.189522 11.00000 0.01569 0.01766 =
0.01683 0.00769 0.00803 0.00509
AFIX 43
H8 2 0.153567 0.526738 0.204040 11.00000 -1.20000
AFIX 0
C9 1 0.244821 0.618282 0.120027 11.00000 0.01771 0.01903 =
0.01733 0.00927 0.00632 0.00811
C10 1 0.364773 0.643003 0.097396 11.00000 0.02145 0.02107 =
0.01937 0.01294 0.00756 0.00343
C11 1 0.477141 0.590835 0.146263 11.00000 0.01435 0.02743 =
0.02324 0.01431 0.00826 0.00215
C12 1 0.472103 0.515311 0.216285 11.00000 0.01324 0.02187 =
0.01968 0.01138 0.00576 0.00395
AFIX 43
H12 2 0.550612 0.480446 0.249088 11.00000 -1.20000
AFIX 0
C13 1 0.555676 0.189728 0.458641 11.00000 0.01137 0.01506 =
0.01876 0.00744 0.00501 0.00324
C14 1 0.636420 0.158935 0.390187 11.00000 0.01554 0.02113 =
0.02399 0.01229 0.00965 0.00647
AFIX 43
H14 2 0.616529 0.178425 0.316355 11.00000 -1.20000
AFIX 0
C15 1 0.745003 0.100189 0.430218 11.00000 0.01494 0.02063 =
0.03157 0.01096 0.01300 0.00628
C16 1 0.778249 0.073899 0.538882 11.00000 0.01266 0.01533 =
0.03099 0.01087 0.00448 0.00543
C17 1 0.698079 0.103925 0.606261 11.00000 0.01908 0.01748 =
0.01878 0.00941 0.00246 0.00405
C18 1 0.586540 0.159945 0.566917 11.00000 0.01638 0.01646 =
0.01795 0.00682 0.00572 0.00442
AFIX 43
H18 2 0.530857 0.178250 0.613167 11.00000 -1.20000
AFIX 0
C19 1 0.055532 0.119083 0.178331 11.00000 0.01734 0.02144 =
0.01391 0.00207 0.00868 0.00082
AFIX 23
H19A 2 0.133882 0.074765 0.186811 11.00000 -1.20000
H19B 2 0.069151 0.183513 0.139977 11.00000 -1.20000
AFIX 0
C20 1 -0.086289 0.022502 0.095978 11.00000 0.01740 0.01766 =
0.01237 0.00376 0.00751 0.00290
C21 1 -0.105096 -0.104013 0.092766 11.00000 0.02618 0.02009 =
0.01729 0.00817 0.00805 0.00480
AFIX 43
H21 2 -0.026123 -0.131530 0.138389 11.00000 -1.20000
AFIX 0
C22 1 -0.239028 -0.190222 0.023036 11.00000 0.03532 0.02081 =
0.02259 0.00656 0.01162 -0.00304
AFIX 43
H22 2 -0.251573 -0.276441 0.021264 11.00000 -1.20000
AFIX 0
C23 1 -0.354296 -0.150408 -0.043921 11.00000 0.02261 0.03275 =
0.02450 0.00216 0.00614 -0.00721
AFIX 43
H23 2 -0.445992 -0.209187 -0.091104 11.00000 -1.20000
AFIX 0
C24 1 -0.335877 -0.024949 -0.042084 11.00000 0.01952 0.03508 =
0.02789 0.00653 0.00227 0.00661
AFIX 43
H24 2 -0.414817 0.002129 -0.088398 11.00000 -1.20000
AFIX 0
C25 1 -0.201978 0.061297 0.027476 11.00000 0.02356 0.02064 =
0.02174 0.00640 0.00583 0.00662
AFIX 43
H25 2 -0.189487 0.147140 0.028195 11.00000 -1.20000
AFIX 0
B1 3 0.202178 0.299623 0.404951 11.00000 0.01258 0.01345 =
0.01448 0.00631 0.00632 0.00408
B2 3 0.338381 0.401522 0.314514 11.00000 0.01395 0.01391 =
0.01482 0.00619 0.00521 0.00302
B3 3 0.432154 0.257592 0.415502 11.00000 0.01271 0.01512 =
0.01550 0.00659 0.00504 0.00409
HKLF 4
REM 15srv091 in P-1
REM R1 = 0.0358 for 6223 Fo > 4sig(Fo) and 0.0432 for all 7267 data
REM 379 parameters refined using 0 restraints
END
WGHT 0.0491 0.4686
REM Highest difference peak 0.455, deepest hole -0.217, 1-sigma level 0.049
Q1 1 0.3460 0.4469 0.2711 11.00000 0.05 0.46
Q2 1 0.4925 0.2223 0.4411 11.00000 0.05 0.43
Q3 1 0.2999 0.6194 0.1018 11.00000 0.05 0.41
Q4 1 0.1822 0.3344 0.4634 11.00000 0.05 0.41
Q5 1 0.2484 0.5838 0.1541 11.00000 0.05 0.39
Q6 1 0.4743 0.5517 0.1868 11.00000 0.05 0.39
Q7 1 0.1207 0.3379 0.6395 11.00000 0.05 0.38
REM The information below was added by Olex2.
REM
REM R1 = 0.0358 for 6223 Fo > 4sig(Fo) and 0.0432 for all 27452 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.46, deepest hole -0.22
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0432
REM R1_gt = 0.0358
REM wR_ref = 0.1003
REM GOOF = 1.034
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 27452
REM Reflections_gt = 6223
REM Parameters = n/a
REM Hole = -0.22
REM Peak = 0.46
REM Flack = n/a
;
#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_7a_16srv413
_database_code_depnum_ccdc_archive 'CCDC 1563950'
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2016-11-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common ?
_chemical_name_systematic 3,4,5-trifluorophenylboroxine
_chemical_formula_moiety 'C18 H6 B3 F9 O3'
_chemical_formula_sum 'C18 H6 B3 F9 O3'
_chemical_formula_weight 473.66
_chemical_melting_point ?
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'
F F 0.0171 0.0103 '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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 60
_space_group_name_H-M_alt 'P b c n'
_space_group_name_Hall '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
_cell_length_a 17.083(4)
_cell_length_b 13.093(3)
_cell_length_c 7.990(2)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1787.0(8)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7348
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 31.51
_cell_measurement_theta_min 2.38
_shelx_estimated_absorpt_T_max 0.979
_shelx_estimated_absorpt_T_min 0.974
_exptl_absorpt_coefficient_mu 0.177
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8873
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1096 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8873.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.761
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description irregular
_exptl_crystal_F_000 936
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0792
_diffrn_reflns_av_unetI/netI 0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 22891
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.996
_diffrn_reflns_theta_min 2.385
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1466
_reflns_number_total 2162
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max 0.312
_refine_diff_density_min -0.296
_refine_diff_density_rms 0.054
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 164
_refine_ls_number_reflns 2162
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0781
_refine_ls_R_factor_gt 0.0445
_refine_ls_restrained_S_all 1.049
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1031
_refine_ls_wR_factor_ref 0.1170
_refine_special_details ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33544(7) 0.35130(7) 0.46045(15) 0.0326(3) Uani 1 1 d . . . . .
F2 F 0.22161(6) 0.44746(9) 0.29114(15) 0.0335(3) Uani 1 1 d . . . . .
F3 F 0.21638(6) 0.65261(8) 0.27961(14) 0.0327(3) Uani 1 1 d . . . . .
F4 F 0.39036(7) 1.16468(8) 0.57511(16) 0.0369(3) Uani 1 1 d . . . . .
F5 F 0.5000 1.26713(11) 0.7500 0.0348(4) Uani 1 2 d S T P . .
O1 O 0.44870(6) 0.78147(8) 0.64872(14) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.5000 0.62463(13) 0.7500 0.0183(4) Uani 1 2 d S T P . .
C1 C 0.38609(10) 0.61550(13) 0.5480(2) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.38885(10) 0.50893(13) 0.5496(2) 0.0186(4) Uani 1 1 d . . . . .
C3 C 0.33357(10) 0.45441(13) 0.4628(2) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.27511(10) 0.50259(14) 0.3749(2) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.27302(10) 0.60771(14) 0.3709(2) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.32735(11) 0.66504(14) 0.4567(2) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.5000 0.95231(17) 0.7500 0.0166(5) Uani 1 2 d S T P . .
C8 C 0.44291(11) 1.00589(13) 0.6615(2) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.44401(10) 1.11117(14) 0.6623(2) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.5000 1.16430(18) 0.7500 0.0238(6) Uani 1 2 d S T P . .
B1 B 0.44702(11) 0.67698(15) 0.6521(2) 0.0172(4) Uani 1 1 d . . . . .
B2 B 0.5000 0.8344(2) 0.7500 0.0152(6) Uani 1 2 d S T P . .
H2 H 0.4302(12) 0.4749(15) 0.609(2) 0.029(5) Uiso 1 1 d . . . . .
H8 H 0.4018(10) 0.9701(13) 0.600(2) 0.013(4) Uiso 1 1 d . . . . .
H6 H 0.3262(11) 0.7341(16) 0.451(2) 0.025(5) 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
F1 0.0399(7) 0.0136(6) 0.0443(7) -0.0025(5) -0.0106(6) -0.0027(5)
F2 0.0270(6) 0.0330(7) 0.0406(7) -0.0090(5) -0.0135(5) -0.0056(5)
F3 0.0270(6) 0.0346(7) 0.0366(7) -0.0011(5) -0.0157(5) 0.0093(5)
F4 0.0368(7) 0.0243(6) 0.0495(8) 0.0130(5) -0.0046(6) 0.0101(5)
F5 0.0435(10) 0.0115(7) 0.0493(11) 0.000 0.0140(8) 0.000
O1 0.0189(6) 0.0141(6) 0.0204(6) 0.0010(5) -0.0027(5) 0.0008(5)
O2 0.0181(8) 0.0124(8) 0.0246(9) 0.000 -0.0059(7) 0.000
C1 0.0162(8) 0.0170(9) 0.0180(9) -0.0001(7) 0.0013(7) -0.0011(7)
C2 0.0176(8) 0.0194(9) 0.0189(9) 0.0019(7) -0.0016(7) 0.0010(7)
C3 0.0253(9) 0.0154(9) 0.0226(9) -0.0031(7) 0.0000(7) 0.0001(7)
C4 0.0185(9) 0.0252(11) 0.0220(9) -0.0057(8) -0.0037(8) -0.0033(8)
C5 0.0180(9) 0.0253(10) 0.0198(9) -0.0008(8) -0.0035(7) 0.0055(8)
C6 0.0204(9) 0.0172(9) 0.0206(9) -0.0007(7) -0.0002(7) 0.0031(7)
C7 0.0175(11) 0.0160(12) 0.0163(11) 0.000 0.0061(9) 0.000
C8 0.0200(9) 0.0173(9) 0.0209(9) 0.0021(7) 0.0031(7) -0.0006(7)
C9 0.0229(9) 0.0186(9) 0.0249(9) 0.0051(8) 0.0067(8) 0.0061(8)
C10 0.0316(14) 0.0109(12) 0.0289(14) 0.000 0.0140(12) 0.000
B1 0.0164(9) 0.0162(10) 0.0192(9) 0.0011(8) 0.0011(8) 0.0001(8)
B2 0.0147(13) 0.0177(14) 0.0133(13) 0.000 0.0051(10) 0.000
_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 C3 1.350(2) . ?
F2 C4 1.3432(19) . ?
F3 C5 1.3468(19) . ?
F4 C9 1.348(2) . ?
F5 C10 1.346(3) . ?
O1 B1 1.369(2) . ?
O1 B2 1.3797(18) . ?
O2 B1 1.379(2) 4_656 ?
O2 B1 1.379(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.400(2) . ?
C1 B1 1.556(3) . ?
C2 C3 1.372(2) . ?
C2 H2 0.96(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.377(3) . ?
C5 C6 1.377(2) . ?
C6 H6 0.91(2) . ?
C7 C8 1.394(2) 4_656 ?
C7 C8 1.394(2) . ?
C7 B2 1.544(3) . ?
C8 C9 1.379(2) . ?
C8 H8 0.979(18) . ?
C9 C10 1.375(2) . ?
C10 C9 1.375(2) 4_656 ?
B2 O1 1.3797(18) 4_656 ?
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
B1 O1 B2 120.26(15) . . ?
B1 O2 B1 120.4(2) 4_656 . ?
C2 C1 C6 119.47(16) . . ?
C2 C1 B1 119.31(15) . . ?
C6 C1 B1 121.20(16) . . ?
C1 C2 H2 119.5(12) . . ?
C3 C2 C1 119.49(16) . . ?
C3 C2 H2 121.0(12) . . ?
F1 C3 C2 120.72(16) . . ?
F1 C3 C4 117.97(15) . . ?
C2 C3 C4 121.31(16) . . ?
F2 C4 C3 120.15(16) . . ?
F2 C4 C5 120.52(16) . . ?
C3 C4 C5 119.31(16) . . ?
F3 C5 C4 117.87(16) . . ?
F3 C5 C6 121.06(16) . . ?
C6 C5 C4 121.06(16) . . ?
C1 C6 H6 120.3(13) . . ?
C5 C6 C1 119.35(17) . . ?
C5 C6 H6 120.4(13) . . ?
C8 C7 C8 119.6(2) 4_656 . ?
C8 C7 B2 120.22(11) . . ?
C8 C7 B2 120.22(11) 4_656 . ?
C7 C8 H8 121.1(10) . . ?
C9 C8 C7 119.44(18) . . ?
C9 C8 H8 119.4(10) . . ?
F4 C9 C8 120.55(17) . . ?
F4 C9 C10 118.27(17) . . ?
C10 C9 C8 121.17(18) . . ?
F5 C10 C9 120.39(11) . . ?
F5 C10 C9 120.40(12) . 4_656 ?
C9 C10 C9 119.2(2) . 4_656 ?
O1 B1 O2 119.64(16) . . ?
O1 B1 C1 121.36(16) . . ?
O2 B1 C1 119.00(16) . . ?
O1 B2 O1 119.7(2) . 4_656 ?
O1 B2 C7 120.16(11) . . ?
O1 B2 C7 120.16(11) 4_656 . ?
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
C2 C1 B1 O1 177.16(16) . . . . ?
C2 C1 B1 O2 -3.1(2) . . . . ?
C6 C1 B1 O1 -4.6(3) . . . . ?
C6 C1 B1 O2 175.11(15) . . . . ?
C8 C7 B2 O1 -173.22(10) 4_656 . . . ?
C8 C7 B2 O1 -173.22(10) . . . 4_656 ?
C8 C7 B2 O1 6.78(10) 4_656 . . 4_656 ?
C8 C7 B2 O1 6.78(10) . . . . ?
B1 O1 B2 O1 1.91(11) . . . 4_656 ?
B1 O1 B2 C7 -178.09(11) . . . . ?
B1 O2 B1 O1 1.89(11) 4_656 . . . ?
B1 O2 B1 C1 -177.84(18) 4_656 . . . ?
B2 O1 B1 O2 -3.8(2) . . . . ?
B2 O1 B1 C1 175.94(12) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
TITL 16srv413
CELL 0.71073 17.0825 13.0934 7.9897 90 90 90
ZERR 4 0.0043 0.0032 0.0022 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,+Y,0.5-Z
SFAC C H B F O
UNIT 72 24 12 36 12
EQIV $1 1-X,+Y,1.5-Z
L.S. 9
PLAN 5
SIZE 0.12 0.13 0.15
TEMP -153.15
CONF C8 C7 B2 O1
CONF C8 C7 B2 O1_$1
CONF C8_$1 C7 B2 O1
CONF C8_$1 C7 B2 O1_$1
CONF B1 O1 B2 O1_$1
CONF B1 O1 B2 C7
CONF B2 O1 B1 O2
CONF B2 O1 B1 C1
CONF C2 C1 B1 O1
CONF C2 C1 B1 O2
CONF C6 C1 B1 O1
CONF C6 C1 B1 O2
CONF B1_$1 O2 B1 O1
CONF B1_$1 O2 B1 C1
BOND $h
fmap 2
acta
OMIT -2 56
OMIT 2 19 1
WGHT 0.06 0.25
FVAR 0.16287
REM
REM
REM
F1 4 0.33544 0.35130 0.46046 11.00000 0.03983 0.01361 0.04425 =
-0.00254 -0.01060 -0.00272
F2 4 0.22162 0.44746 0.29114 11.00000 0.02690 0.03296 0.04061 =
-0.00895 -0.01354 -0.00562
F3 4 0.21638 0.65261 0.27962 11.00000 0.02690 0.03462 0.03661 =
-0.00107 -0.01576 0.00929
F4 4 0.39035 1.16469 0.57510 11.00000 0.03676 0.02427 0.04951 =
0.01304 -0.00455 0.01005
F5 4 0.50000 1.26713 0.75000 10.50000 0.04348 0.01146 0.04927 =
0.00000 0.01400 0.00000
O1 5 0.44870 0.78147 0.64871 11.00000 0.01882 0.01414 0.02037 =
0.00105 -0.00274 0.00078
O2 5 0.50000 0.62463 0.75000 10.50000 0.01808 0.01235 0.02452 =
0.00000 -0.00587 0.00000
C1 1 0.38610 0.61550 0.54803 11.00000 0.01614 0.01699 0.01798 =
-0.00013 0.00124 -0.00108
C2 1 0.38886 0.50893 0.54963 11.00000 0.01759 0.01935 0.01896 =
0.00192 -0.00159 0.00098
C3 1 0.33357 0.45439 0.46281 11.00000 0.02523 0.01544 0.02258 =
-0.00315 -0.00004 0.00011
C4 1 0.27510 0.50260 0.37490 11.00000 0.01847 0.02521 0.02208 =
-0.00564 -0.00366 -0.00328
C5 1 0.27301 0.60771 0.37089 11.00000 0.01798 0.02520 0.01983 =
-0.00080 -0.00353 0.00556
C6 1 0.32734 0.66505 0.45672 11.00000 0.02037 0.01726 0.02059 =
-0.00067 -0.00017 0.00308
C7 1 0.50000 0.95231 0.75000 10.50000 0.01746 0.01594 0.01631 =
0.00000 0.00612 -0.00000
C8 1 0.44291 1.00588 0.66150 11.00000 0.02007 0.01725 0.02097 =
0.00211 0.00312 -0.00059
C9 1 0.44400 1.11117 0.66226 11.00000 0.02283 0.01848 0.02494 =
0.00507 0.00668 0.00607
C10 1 0.50000 1.16431 0.75000 10.50000 0.03156 0.01089 0.02887 =
0.00000 0.01396 0.00000
B1 3 0.44702 0.67700 0.65212 11.00000 0.01637 0.01612 0.01915 =
0.00112 0.00103 0.00009
B2 3 0.50000 0.83441 0.75000 10.50000 0.01477 0.01754 0.01339 =
0.00000 0.00510 -0.00000
H2 2 0.43042 0.47486 0.60935 11.00000 0.02877
H8 2 0.40179 0.97003 0.59943 11.00000 0.01291
H6 2 0.32629 0.73406 0.45101 11.00000 0.02526
HKLF 4
END
;
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform, pentane'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_10d_16srv262
_database_code_depnum_ccdc_archive 'CCDC 1551622'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2017-02-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic
'phenylboroxine complex with 4 equiv. benzylamine '
_chemical_formula_moiety 'C32 H33 B3 N2 O3, 2(C7 H9 N)'
_chemical_formula_sum 'C46 H51 B3 N4 O3'
_chemical_formula_weight 740.33
_chemical_melting_point 329.4(3)
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 21.2120(9)
_cell_length_b 11.2705(5)
_cell_length_c 18.8494(8)
_cell_angle_alpha 90
_cell_angle_beta 114.8857(16)
_cell_angle_gamma 90
_cell_volume 4087.9(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9868
_cell_measurement_temperature 120
_cell_measurement_theta_max 26.839
_cell_measurement_theta_min 2.18
_shelx_estimated_absorpt_T_max 0.991
_shelx_estimated_absorpt_T_min 0.979
_exptl_absorpt_coefficient_mu 0.074
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9421
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker, 2014) was used for absorption correction.
wR2(int) was 0.1307 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.9421.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.203
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description irregular
_exptl_crystal_F_000 1576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 2.00 1.00 0.0730
0.00 -2.00 -1.00 0.0670
-1.00 0.00 2.00 0.1330
1.00 0.00 -2.00 0.0920
-1.00 -2.00 1.00 0.0920
-1.00 0.00 0.00 0.0640
1.00 0.00 0.00 0.0490
1.00 -1.00 -2.00 0.0990
-1.00 2.00 2.00 0.0940
_exptl_crystal_size_max 0.294
_exptl_crystal_size_mid 0.164
_exptl_crystal_size_min 0.128
_exptl_special_details
;
Data were collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of 340 narrow-frame \w-scans (scan
width 0.5\%, 10s exposure), every run at a different \f angle.
Two runs of 358 \f-scans (scan width 1\%, 1.5s exposure) were used for
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0559
_diffrn_reflns_av_unetI/netI 0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 68095
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 25.998
_diffrn_reflns_theta_max 25.998
_diffrn_reflns_theta_min 2.117
_diffrn_ambient_temperature 120.0
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type D8V
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6020
_reflns_number_total 8022
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2014/5 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection 'APEX3 v.2016.1_0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.307
_refine_diff_density_min -0.276
_refine_diff_density_rms 0.038
_refine_ls_extinction_coef 0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 584
_refine_ls_number_reflns 8022
_refine_ls_number_restraints 604
_refine_ls_R_factor_all 0.0740
_refine_ls_R_factor_gt 0.0496
_refine_ls_restrained_S_all 1.030
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+2.5270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1053
_refine_ls_wR_factor_ref 0.1169
_refine_special_details
; Amino H atoms: refall, other H atoms: riding model (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Restrained distances
C2-C3B \\sim C2-C7B \\sim C4B-C3B \\sim C4A-C3A \\sim C5A-C4A \\sim C5B-C4B
\\sim C6B-C5B \\sim C6A-C5A ~
C7A-C6A \\sim C7B-C6B \\sim C2-C3A \\sim C2-C7A
with sigma of 0.02
C40B-C35B \\sim C40A-C35A \\sim C40B-C39B \\sim C40A-C39A \\sim C39B-C38B
\\sim C39A-C38A \\sim C38B-
C37B \\sim C38A-C37A \\sim C37A-C36A \\sim C37B-C36B \\sim C36B-C35B \\sim
C36A-C35A
with sigma of 0.02
C35B-C34 \\sim C35A-C34
with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C35B) = Uanis(C35A)
Uanis(C7A) = Uanis(C7B)
Uanis(C6A) = Uanis(C6B)
Uanis(C5A) = Uanis(C5B)
Uanis(C4A) = Uanis(C4B)
Uanis(C3A) = Uanis(C3B)
4. Rigid body (RIGU) restrains
All non-hydrogen atoms
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
Fixed Sof: C3A(0.5) H3A(0.5) C4A(0.5) H4A(0.5) C5A(0.5) H5A(0.5) C6A(0.5)
H6A(0.5) C7A(0.5) H7A(0.5) C3B(0.5) H3B(0.5) C4B(0.5) H4B(0.5) C5B(0.5)
H5B(0.5) C6B(0.5) H6B(0.5) C7B(0.5) H7B(0.5) C35A(0.7) C36A(0.7) H36A(0.7)
C37A(0.7) H37A(0.7) C38A(0.7) H38A(0.7) C39A(0.7) H39A(0.7) C40A(0.7)
H40A(0.7) C35B(0.3) C36B(0.3) H36B(0.3) C37B(0.3) H37B(0.3) C38B(0.3)
H38B(0.3) C39B(0.3) H39B(0.3) C40B(0.3) H40B(0.3)
6.a Secondary CH2 refined with riding coordinates:
C1(H1C,H1D), C14(H14A,H14B), C41(H41A,H41B)
6.b Aromatic/amide H refined with riding coordinates:
C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B),
C5B(H5B), C6B(H6B), C7B(H7B), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
C36A(H36A), C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A), C36B(H36B),
C37B(H37B), C38B(H38B), C39B(H39B), C40B(H40B), C43(H43), C44(H44), C45(H45),
C46(H46), C47(H47)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22959(6) 0.75175(11) 0.51854(6) 0.0277(3) Uani 1 1 d . U . . .
O2 O 0.27823(6) 0.92207(11) 0.47857(6) 0.0244(3) Uani 1 1 d . U . . .
O3 O 0.23307(6) 0.75934(10) 0.39101(6) 0.0234(3) Uani 1 1 d . U . . .
N1 N 0.12495(8) 0.70955(17) 0.40085(9) 0.0302(4) Uani 1 1 d . U . . .
H1A H 0.1056(11) 0.6751(19) 0.4317(13) 0.046(6) Uiso 1 1 d . . . . .
H1B H 0.1145(11) 0.791(2) 0.3991(13) 0.049(7) Uiso 1 1 d . . . . .
N2 N 0.35618(7) 0.79398(14) 0.58411(8) 0.0232(3) Uani 1 1 d . U . . .
H2A H 0.3604(9) 0.7537(17) 0.5442(11) 0.031(5) Uiso 1 1 d . . . . .
H2B H 0.3900(10) 0.8533(18) 0.5997(11) 0.036(5) Uiso 1 1 d . . . . .
C1 C 0.09115(9) 0.6620(2) 0.31985(11) 0.0392(5) Uani 1 1 d . U . . .
H1C H 0.1059 0.5787 0.3197 0.047 Uiso 1 1 calc R . . . .
H1D H 0.1069 0.7084 0.2857 0.047 Uiso 1 1 calc R . . . .
C3A C -0.0143(4) 0.5751(13) 0.3151(10) 0.0504(14) Uani 0.5 1 d D U P A 1
H3A H 0.0157 0.5171 0.3493 0.061 Uiso 0.5 1 calc R . P A 1
C4A C -0.0851(4) 0.5683(8) 0.2930(5) 0.0637(15) Uani 0.5 1 d D U P A 1
H4A H -0.1044 0.5041 0.3100 0.076 Uiso 0.5 1 calc R . P A 1
C5A C -0.1269(3) 0.6554(6) 0.2464(4) 0.0504(13) Uani 0.5 1 d D U P A 1
H5A H -0.1754 0.6522 0.2323 0.061 Uiso 0.5 1 calc R . P A 1
C6A C -0.1005(4) 0.7479(7) 0.2194(5) 0.0444(13) Uani 0.5 1 d D U P A 1
H6A H -0.1310 0.8057 0.1854 0.053 Uiso 0.5 1 calc R . P A 1
C7A C -0.0283(6) 0.7565(15) 0.2421(10) 0.0398(19) Uani 0.5 1 d D U P A 1
H7A H -0.0090 0.8223 0.2267 0.048 Uiso 0.5 1 calc R . P A 1
C3B C -0.0298(4) 0.5884(13) 0.3014(10) 0.0504(14) Uani 0.5 1 d D U P A 2
H3B H -0.0098 0.5232 0.3355 0.061 Uiso 0.5 1 calc R . P A 2
C4B C -0.1001(4) 0.6011(8) 0.2679(5) 0.0637(15) Uani 0.5 1 d D U P A 2
H4B H -0.1281 0.5466 0.2803 0.076 Uiso 0.5 1 calc R . P A 2
C5B C -0.1311(3) 0.6924(6) 0.2162(4) 0.0504(13) Uani 0.5 1 d D U P A 2
H5B H -0.1803 0.6997 0.1926 0.061 Uiso 0.5 1 calc R . P A 2
C6B C -0.0908(4) 0.7737(8) 0.1985(5) 0.0444(13) Uani 0.5 1 d D U P A 2
H6B H -0.1113 0.8389 0.1646 0.053 Uiso 0.5 1 calc R . P A 2
C7B C -0.0182(6) 0.7561(15) 0.2326(11) 0.0398(19) Uani 0.5 1 d D U P A 2
H7B H 0.0101 0.8066 0.2178 0.048 Uiso 0.5 1 calc R . P A 2
C8 C 0.22859(8) 0.55644(16) 0.45025(9) 0.0237(4) Uani 1 1 d . U . . .
C9 C 0.20624(10) 0.47845(18) 0.49271(10) 0.0341(5) Uani 1 1 d . U . . .
H9 H 0.1781 0.5084 0.5167 0.041 Uiso 1 1 calc R . . . .
C10 C 0.22362(12) 0.35925(19) 0.50115(12) 0.0434(5) Uani 1 1 d . U . . .
H10 H 0.2076 0.3092 0.5306 0.052 Uiso 1 1 calc R . . . .
C11 C 0.26423(12) 0.31309(19) 0.46682(12) 0.0434(5) Uani 1 1 d . U . . .
H11 H 0.2763 0.2313 0.4723 0.052 Uiso 1 1 calc R . . . .
C12 C 0.28704(11) 0.38703(18) 0.42453(12) 0.0388(5) Uani 1 1 d . U . . .
H12 H 0.3151 0.3563 0.4006 0.047 Uiso 1 1 calc R . . . .
C13 C 0.26931(9) 0.50635(17) 0.41658(10) 0.0283(4) Uani 1 1 d . U . . .
H13 H 0.2856 0.5557 0.3870 0.034 Uiso 1 1 calc R . . . .
C14 C 0.36971(10) 0.70845(17) 0.64888(10) 0.0314(4) Uani 1 1 d . U . . .
H14A H 0.3305 0.6517 0.6331 0.038 Uiso 1 1 calc R . . . .
H14B H 0.3717 0.7522 0.6953 0.038 Uiso 1 1 calc R . . . .
C15 C 0.43617(9) 0.64035(16) 0.67077(10) 0.0265(4) Uani 1 1 d . U . . .
C16 C 0.43563(10) 0.52636(17) 0.64249(10) 0.0299(4) Uani 1 1 d . U . . .
H16 H 0.3927 0.4900 0.6102 0.036 Uiso 1 1 calc R . . . .
C17 C 0.49715(11) 0.46523(18) 0.66100(11) 0.0372(5) Uani 1 1 d . U . . .
H17 H 0.4962 0.3874 0.6412 0.045 Uiso 1 1 calc R . . . .
C18 C 0.55990(11) 0.5171(2) 0.70815(12) 0.0412(5) Uani 1 1 d . U . . .
H18 H 0.6021 0.4753 0.7206 0.049 Uiso 1 1 calc R . . . .
C19 C 0.56094(10) 0.6294(2) 0.73690(12) 0.0413(5) Uani 1 1 d . U . . .
H19 H 0.6041 0.6649 0.7696 0.050 Uiso 1 1 calc R . . . .
C20 C 0.49989(10) 0.69100(18) 0.71873(10) 0.0337(4) Uani 1 1 d . U . . .
H20 H 0.5013 0.7686 0.7391 0.040 Uiso 1 1 calc R . . . .
C21 C 0.26231(8) 0.93086(16) 0.60577(9) 0.0225(4) Uani 1 1 d . U . . .
C22 C 0.24330(11) 0.8784(2) 0.66070(12) 0.0425(5) Uani 1 1 d . U . . .
H22 H 0.2405 0.7943 0.6618 0.051 Uiso 1 1 calc R . . . .
C23 C 0.22834(12) 0.9438(2) 0.71380(13) 0.0494(6) Uani 1 1 d . U . . .
H23 H 0.2165 0.9046 0.7511 0.059 Uiso 1 1 calc R . . . .
C24 C 0.23072(9) 1.0663(2) 0.71243(11) 0.0369(5) Uani 1 1 d . U . . .
H24 H 0.2195 1.1120 0.7479 0.044 Uiso 1 1 calc R . . . .
C25 C 0.24954(10) 1.12122(18) 0.65901(11) 0.0366(5) Uani 1 1 d . U . . .
H25 H 0.2515 1.2053 0.6576 0.044 Uiso 1 1 calc R . . . .
C26 C 0.26564(9) 1.05369(17) 0.60715(10) 0.0291(4) Uani 1 1 d . U . . .
H26 H 0.2794 1.0931 0.5714 0.035 Uiso 1 1 calc R . . . .
C27 C 0.26854(8) 0.94273(16) 0.34036(9) 0.0248(4) Uani 1 1 d . U . . .
C28 C 0.24315(9) 0.89757(18) 0.26442(10) 0.0299(4) Uani 1 1 d . U . . .
H28 H 0.2175 0.8255 0.2525 0.036 Uiso 1 1 calc R . . . .
C29 C 0.25454(11) 0.95572(19) 0.20598(11) 0.0374(5) Uani 1 1 d . U . . .
H29 H 0.2362 0.9240 0.1545 0.045 Uiso 1 1 calc R . . . .
C30 C 0.29232(11) 1.0594(2) 0.22250(12) 0.0423(5) Uani 1 1 d . U . . .
H30 H 0.3011 1.0980 0.1828 0.051 Uiso 1 1 calc R . . . .
C31 C 0.31756(11) 1.10750(19) 0.29700(12) 0.0407(5) Uani 1 1 d . U . . .
H31 H 0.3432 1.1795 0.3085 0.049 Uiso 1 1 calc R . . . .
C32 C 0.30490(9) 1.04902(17) 0.35470(11) 0.0313(4) Uani 1 1 d . U . . .
H32 H 0.3217 1.0829 0.4055 0.038 Uiso 1 1 calc R . . . .
B1 B 0.21031(10) 0.69640(19) 0.44409(11) 0.0241(4) Uani 1 1 d . U . . .
B2 B 0.27542(10) 0.85080(19) 0.54263(11) 0.0238(4) Uani 1 1 d . U . . .
B3 B 0.25884(9) 0.87163(19) 0.40729(11) 0.0229(4) Uani 1 1 d . U . . .
N3 N 0.10168(11) 0.9643(3) 0.4106(2) 0.0669(8) Uani 1 1 d . U . . .
H3C H 0.124(2) 1.012(4) 0.409(3) 0.134(19) Uiso 1 1 d . . . . .
H3D H 0.127(2) 0.964(4) 0.468(2) 0.129(15) Uiso 1 1 d . . . . .
C34 C 0.03431(12) 0.9834(2) 0.40843(15) 0.0455(5) Uani 1 1 d D U . . .
H34A H 0.0227(16) 0.920(3) 0.4341(18) 0.096(10) Uiso 1 1 d . . . . .
H34B H -0.0001(15) 0.970(3) 0.3478(18) 0.091(10) Uiso 1 1 d . . . . .
C35A C 0.0161(4) 1.1012(7) 0.4315(5) 0.0336(8) Uani 0.7 1 d D U P B 1
C36A C -0.05225(19) 1.1354(3) 0.40394(18) 0.0416(8) Uani 0.7 1 d D U P B 1
H36A H -0.0876 1.0843 0.3698 0.050 Uiso 0.7 1 calc R . P B 1
C37A C -0.07038(19) 1.2431(3) 0.4250(2) 0.0473(9) Uani 0.7 1 d D U P B 1
H37A H -0.1179 1.2655 0.4053 0.057 Uiso 0.7 1 calc R . P B 1
C38A C -0.0200(2) 1.3177(3) 0.4742(3) 0.0396(7) Uani 0.7 1 d D U P B 1
H38A H -0.0322 1.3934 0.4867 0.048 Uiso 0.7 1 calc R . P B 1
C39A C 0.04809(19) 1.2825(3) 0.5051(3) 0.0592(11) Uani 0.7 1 d D U P B 1
H39A H 0.0831 1.3314 0.5418 0.071 Uiso 0.7 1 calc R . P B 1
C40A C 0.06556(17) 1.1747(3) 0.4824(3) 0.0508(9) Uani 0.7 1 d D U P B 1
H40A H 0.1130 1.1517 0.5027 0.061 Uiso 0.7 1 calc R . P B 1
C35B C 0.0278(10) 1.1031(18) 0.4469(12) 0.0336(8) Uani 0.3 1 d D U P B 2
C36B C -0.0310(5) 1.1759(8) 0.4048(6) 0.050(3) Uiso 0.3 1 d D U P B 2
H36B H -0.0632 1.1513 0.3542 0.060 Uiso 0.3 1 calc R . P B 2
C37B C -0.0430(6) 1.2814(9) 0.4349(6) 0.053(3) Uiso 0.3 1 d D U P B 2
H37B H -0.0837 1.3267 0.4069 0.064 Uiso 0.3 1 calc R . P B 2
C38B C 0.0064(5) 1.3194(9) 0.5075(5) 0.044(3) Uiso 0.3 1 d D U P B 2
H38B H -0.0009 1.3917 0.5290 0.053 Uiso 0.3 1 calc R . P B 2
C39B C 0.0653(4) 1.2539(7) 0.5486(5) 0.045(2) Uiso 0.3 1 d D U P B 2
H39B H 0.0989 1.2818 0.5976 0.054 Uiso 0.3 1 calc R . P B 2
C40B C 0.0757(4) 1.1481(7) 0.5187(4) 0.032(2) Uiso 0.3 1 d D U P B 2
H40B H 0.1167 1.1040 0.5477 0.038 Uiso 0.3 1 calc R . P B 2
N4 N 0.47811(9) 0.96383(16) 0.62888(11) 0.0375(4) Uani 1 1 d . U . . .
H4C H 0.4985(14) 1.007(2) 0.6812(17) 0.080(9) Uiso 1 1 d . . . . .
H4D H 0.5166(15) 0.929(3) 0.6174(17) 0.091(10) Uiso 1 1 d . . . . .
C41 C 0.44680(10) 1.05133(19) 0.56884(13) 0.0430(5) Uani 1 1 d . U . . .
H41A H 0.4083 1.0886 0.5774 0.052 Uiso 1 1 calc R . . . .
H41B H 0.4257 1.0091 0.5181 0.052 Uiso 1 1 calc R . . . .
C42 C 0.49193(9) 1.15056(17) 0.56054(11) 0.0308(4) Uani 1 1 d . U . . .
C43 C 0.46231(10) 1.22692(19) 0.49720(11) 0.0379(5) Uani 1 1 d . U . . .
H43 H 0.4154 1.2150 0.4610 0.046 Uiso 1 1 calc R . . . .
C44 C 0.49921(10) 1.31935(19) 0.48565(11) 0.0371(5) Uani 1 1 d . U . . .
H44 H 0.4779 1.3700 0.4416 0.044 Uiso 1 1 calc R . . . .
C45 C 0.56700(9) 1.33866(17) 0.53776(11) 0.0306(4) Uani 1 1 d . U . . .
H45 H 0.5925 1.4030 0.5302 0.037 Uiso 1 1 calc R . . . .
C46 C 0.59781(9) 1.26394(17) 0.60119(11) 0.0305(4) Uani 1 1 d . U . . .
H46 H 0.6447 1.2767 0.6373 0.037 Uiso 1 1 calc R . . . .
C47 C 0.56042(9) 1.16999(17) 0.61243(11) 0.0304(4) Uani 1 1 d . U . . .
H47 H 0.5820 1.1188 0.6561 0.036 Uiso 1 1 calc R . . . .
C2 C 0.01332(9) 0.66690(17) 0.28731(11) 0.0339(4) Uani 1 1 d D U . . .
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
O1 0.0299(7) 0.0372(7) 0.0199(6) -0.0087(5) 0.0142(5) -0.0131(5)
O2 0.0252(6) 0.0324(7) 0.0159(6) -0.0009(5) 0.0090(5) -0.0050(5)
O3 0.0229(6) 0.0311(7) 0.0171(6) -0.0017(5) 0.0092(5) 0.0022(5)
N1 0.0210(8) 0.0402(10) 0.0306(8) -0.0154(7) 0.0119(7) -0.0034(7)
N2 0.0257(8) 0.0275(8) 0.0194(7) -0.0018(6) 0.0122(6) -0.0052(7)
C1 0.0231(9) 0.0550(13) 0.0316(10) -0.0188(9) 0.0038(8) 0.0041(9)
C3A 0.024(3) 0.042(3) 0.064(5) -0.006(2) -0.002(4) -0.009(3)
C4A 0.023(3) 0.059(4) 0.084(5) 0.011(3) -0.003(3) -0.012(2)
C5A 0.0174(14) 0.057(4) 0.063(4) -0.001(2) 0.004(3) -0.004(2)
C6A 0.029(2) 0.040(3) 0.052(4) -0.005(2) 0.0054(18) 0.0048(19)
C7A 0.026(2) 0.0394(12) 0.046(4) -0.0145(19) 0.007(2) 0.002(2)
C3B 0.024(3) 0.042(3) 0.064(5) -0.006(2) -0.002(4) -0.009(3)
C4B 0.023(3) 0.059(4) 0.084(5) 0.011(3) -0.003(3) -0.012(2)
C5B 0.0174(14) 0.057(4) 0.063(4) -0.001(2) 0.004(3) -0.004(2)
C6B 0.029(2) 0.040(3) 0.052(4) -0.005(2) 0.0054(18) 0.0048(19)
C7B 0.026(2) 0.0394(12) 0.046(4) -0.0145(19) 0.007(2) 0.002(2)
C8 0.0188(8) 0.0347(10) 0.0141(8) -0.0037(7) 0.0036(6) -0.0067(7)
C9 0.0430(11) 0.0396(11) 0.0256(9) -0.0103(8) 0.0204(8) -0.0154(9)
C10 0.0648(14) 0.0381(12) 0.0333(11) -0.0002(9) 0.0265(10) -0.0180(10)
C11 0.0601(14) 0.0331(11) 0.0362(11) 0.0061(9) 0.0196(10) 0.0008(10)
C12 0.0419(11) 0.0404(12) 0.0374(11) 0.0115(9) 0.0200(9) 0.0140(9)
C13 0.0225(9) 0.0362(11) 0.0265(9) 0.0085(8) 0.0108(7) 0.0031(8)
C14 0.0359(10) 0.0368(11) 0.0282(10) 0.0078(8) 0.0199(8) -0.0005(8)
C15 0.0300(9) 0.0329(10) 0.0200(9) 0.0053(7) 0.0139(7) -0.0029(8)
C16 0.0347(10) 0.0356(11) 0.0231(9) 0.0026(8) 0.0156(8) -0.0064(8)
C17 0.0512(12) 0.0345(11) 0.0353(11) 0.0087(9) 0.0276(10) 0.0060(9)
C18 0.0361(11) 0.0551(14) 0.0374(11) 0.0187(10) 0.0204(9) 0.0113(10)
C19 0.0297(10) 0.0582(14) 0.0314(11) 0.0094(10) 0.0085(8) -0.0053(10)
C20 0.0401(11) 0.0365(11) 0.0242(9) 0.0005(8) 0.0134(8) -0.0075(9)
C21 0.0156(8) 0.0330(10) 0.0162(8) -0.0026(7) 0.0041(6) -0.0051(7)
C22 0.0602(14) 0.0415(12) 0.0406(12) -0.0174(10) 0.0357(11) -0.0260(10)
C23 0.0625(15) 0.0606(15) 0.0428(12) -0.0217(11) 0.0396(11) -0.0299(12)
C24 0.0298(10) 0.0553(13) 0.0262(10) -0.0150(9) 0.0123(8) -0.0007(9)
C25 0.0429(11) 0.0344(11) 0.0273(10) 0.0000(8) 0.0096(9) 0.0131(9)
C26 0.0315(10) 0.0340(10) 0.0211(9) 0.0055(8) 0.0105(7) 0.0077(8)
C27 0.0201(8) 0.0359(10) 0.0206(8) 0.0053(7) 0.0106(7) 0.0113(7)
C28 0.0303(10) 0.0381(11) 0.0220(9) 0.0042(8) 0.0117(7) 0.0159(8)
C29 0.0488(12) 0.0479(13) 0.0211(9) 0.0111(9) 0.0201(9) 0.0280(10)
C30 0.0571(13) 0.0486(13) 0.0359(11) 0.0213(10) 0.0339(10) 0.0270(11)
C31 0.0478(12) 0.0431(12) 0.0404(12) 0.0147(10) 0.0276(10) 0.0098(10)
C32 0.0325(10) 0.0400(11) 0.0246(9) 0.0059(8) 0.0150(8) 0.0055(8)
B1 0.0189(9) 0.0366(11) 0.0182(9) -0.0058(8) 0.0092(7) -0.0050(8)
B2 0.0218(10) 0.0331(11) 0.0168(9) -0.0007(8) 0.0084(7) -0.0054(8)
B3 0.0141(9) 0.0350(11) 0.0189(9) 0.0012(8) 0.0062(7) 0.0045(8)
N3 0.0329(11) 0.0587(15) 0.099(2) -0.0382(14) 0.0178(12) 0.0069(11)
C34 0.0511(14) 0.0426(13) 0.0555(15) -0.0062(11) 0.0348(12) 0.0015(10)
C35A 0.038(3) 0.0343(11) 0.036(3) 0.0034(17) 0.0235(17) 0.0015(16)
C36A 0.0424(18) 0.0334(18) 0.0364(17) -0.0019(14) 0.0043(14) 0.0014(16)
C37A 0.0382(19) 0.0342(18) 0.058(2) 0.0007(16) 0.0095(16) 0.0104(16)
C38A 0.038(2) 0.0245(16) 0.061(3) -0.0052(18) 0.025(2) 0.0007(15)
C39A 0.0359(19) 0.044(2) 0.102(3) -0.031(2) 0.032(2) -0.0148(15)
C40A 0.0291(17) 0.044(2) 0.084(3) -0.016(2) 0.0285(19) -0.0046(15)
C35B 0.038(3) 0.0343(11) 0.036(3) 0.0034(17) 0.0235(17) 0.0015(16)
N4 0.0389(10) 0.0361(10) 0.0385(10) 0.0030(8) 0.0173(8) -0.0019(8)
C41 0.0317(11) 0.0456(13) 0.0451(12) 0.0087(10) 0.0096(9) -0.0015(9)
C42 0.0272(9) 0.0327(10) 0.0339(10) 0.0009(8) 0.0142(8) 0.0001(8)
C43 0.0302(10) 0.0448(12) 0.0330(10) 0.0040(9) 0.0076(8) -0.0039(9)
C44 0.0361(11) 0.0437(12) 0.0292(10) 0.0096(9) 0.0116(8) 0.0013(9)
C45 0.0288(10) 0.0358(11) 0.0335(10) 0.0049(8) 0.0192(8) -0.0007(8)
C46 0.0219(9) 0.0379(11) 0.0344(10) 0.0024(8) 0.0144(8) 0.0040(8)
C47 0.0307(10) 0.0321(10) 0.0323(10) 0.0089(8) 0.0171(8) 0.0092(8)
C2 0.0211(9) 0.0310(10) 0.0417(11) -0.0183(8) 0.0054(8) -0.0020(8)
_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
O1 B1 1.429(2) . ?
O1 B2 1.423(2) . ?
O2 B2 1.472(2) . ?
O2 B3 1.354(2) . ?
O3 B1 1.464(2) . ?
O3 B3 1.361(2) . ?
N1 C1 1.487(2) . ?
N1 B1 1.650(2) . ?
N2 C14 1.486(2) . ?
N2 B2 1.682(2) . ?
C1 C2 1.501(2) . ?
C3A C4A 1.382(8) . ?
C3A C2 1.395(9) . ?
C4A C5A 1.366(7) . ?
C5A C6A 1.378(7) . ?
C6A C7A 1.409(9) . ?
C7A C2 1.375(9) . ?
C3B C4B 1.361(8) . ?
C3B C2 1.376(9) . ?
C4B C5B 1.379(7) . ?
C5B C6B 1.387(7) . ?
C6B C7B 1.411(9) . ?
C7B C2 1.393(9) . ?
C8 C9 1.399(2) . ?
C8 C13 1.389(2) . ?
C8 B1 1.617(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.374(3) . ?
C12 C13 1.387(3) . ?
C14 C15 1.502(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.393(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.373(3) . ?
C19 C20 1.380(3) . ?
C21 C22 1.391(2) . ?
C21 C26 1.386(3) . ?
C21 B2 1.608(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.383(3) . ?
C24 C25 1.377(3) . ?
C25 C26 1.390(3) . ?
C27 C28 1.396(2) . ?
C27 C32 1.388(3) . ?
C27 B3 1.580(2) . ?
C28 C29 1.388(3) . ?
C29 C30 1.376(3) . ?
C30 C31 1.386(3) . ?
C31 C32 1.391(3) . ?
N3 C34 1.429(3) . ?
C34 C35A 1.497(5) . ?
C34 C35B 1.564(12) . ?
C35A C36A 1.373(7) . ?
C35A C40A 1.364(7) . ?
C36A C37A 1.381(4) . ?
C37A C38A 1.369(5) . ?
C38A C39A 1.369(5) . ?
C39A C40A 1.389(4) . ?
C35B C36B 1.424(12) . ?
C35B C40B 1.402(11) . ?
C36B C37B 1.387(11) . ?
C37B C38B 1.395(10) . ?
C38B C39B 1.376(10) . ?
C39B C40B 1.376(9) . ?
N4 C41 1.436(3) . ?
C41 C42 1.522(3) . ?
C42 C43 1.389(3) . ?
C42 C47 1.385(3) . ?
C43 C44 1.374(3) . ?
C44 C45 1.375(3) . ?
C45 C46 1.381(3) . ?
C46 C47 1.392(3) . ?
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
B2 O1 B1 122.04(13) . . ?
B3 O2 B2 118.99(14) . . ?
B3 O3 B1 120.85(13) . . ?
C1 N1 B1 115.44(13) . . ?
C14 N2 B2 115.83(13) . . ?
N1 C1 C2 112.23(15) . . ?
C4A C3A C2 120.2(8) . . ?
C5A C4A C3A 118.8(8) . . ?
C4A C5A C6A 121.8(6) . . ?
C5A C6A C7A 119.8(8) . . ?
C2 C7A C6A 118.1(10) . . ?
C4B C3B C2 122.0(8) . . ?
C3B C4B C5B 120.7(7) . . ?
C4B C5B C6B 120.3(6) . . ?
C5B C6B C7B 117.6(8) . . ?
C2 C7B C6B 122.0(9) . . ?
C9 C8 B1 121.68(15) . . ?
C13 C8 C9 115.57(17) . . ?
C13 C8 B1 122.71(15) . . ?
C10 C9 C8 122.50(18) . . ?
C11 C10 C9 120.07(19) . . ?
C12 C11 C10 119.0(2) . . ?
C11 C12 C13 120.31(19) . . ?
C12 C13 C8 122.50(17) . . ?
N2 C14 C15 113.05(14) . . ?
C16 C15 C14 120.78(17) . . ?
C16 C15 C20 118.49(17) . . ?
C20 C15 C14 120.72(17) . . ?
C17 C16 C15 120.59(18) . . ?
C18 C17 C16 120.2(2) . . ?
C19 C18 C17 119.66(19) . . ?
C18 C19 C20 120.57(19) . . ?
C19 C20 C15 120.51(19) . . ?
C22 C21 B2 120.45(16) . . ?
C26 C21 C22 116.05(16) . . ?
C26 C21 B2 123.43(15) . . ?
C23 C22 C21 122.6(2) . . ?
C24 C23 C22 119.83(19) . . ?
C25 C24 C23 119.12(18) . . ?
C24 C25 C26 120.06(19) . . ?
C21 C26 C25 122.31(17) . . ?
C28 C27 B3 120.68(17) . . ?
C32 C27 C28 117.21(16) . . ?
C32 C27 B3 122.05(15) . . ?
C29 C28 C27 121.38(19) . . ?
C30 C29 C28 120.05(18) . . ?
C29 C30 C31 120.10(18) . . ?
C30 C31 C32 119.2(2) . . ?
C27 C32 C31 122.06(18) . . ?
O1 B1 O3 114.77(15) . . ?
O1 B1 N1 104.31(13) . . ?
O1 B1 C8 113.23(15) . . ?
O3 B1 N1 103.16(14) . . ?
O3 B1 C8 112.55(14) . . ?
C8 B1 N1 107.66(14) . . ?
O1 B2 O2 115.10(14) . . ?
O1 B2 N2 105.96(15) . . ?
O1 B2 C21 111.62(14) . . ?
O2 B2 N2 101.78(12) . . ?
O2 B2 C21 112.34(15) . . ?
C21 B2 N2 109.21(13) . . ?
O2 B3 O3 122.66(16) . . ?
O2 B3 C27 119.50(17) . . ?
O3 B3 C27 117.80(15) . . ?
N3 C34 C35A 120.2(5) . . ?
N3 C34 C35B 113.5(10) . . ?
C36A C35A C34 120.0(5) . . ?
C40A C35A C34 121.7(5) . . ?
C40A C35A C36A 118.2(4) . . ?
C35A C36A C37A 121.0(4) . . ?
C38A C37A C36A 120.1(3) . . ?
C39A C38A C37A 119.6(3) . . ?
C38A C39A C40A 119.5(3) . . ?
C35A C40A C39A 121.4(4) . . ?
C36B C35B C34 117.8(9) . . ?
C40B C35B C34 126.2(9) . . ?
C40B C35B C36B 116.0(10) . . ?
C37B C36B C35B 122.3(10) . . ?
C36B C37B C38B 118.3(10) . . ?
C39B C38B C37B 121.1(10) . . ?
C38B C39B C40B 119.9(8) . . ?
C39B C40B C35B 122.3(8) . . ?
N4 C41 C42 118.89(17) . . ?
C43 C42 C41 117.82(17) . . ?
C47 C42 C41 124.16(17) . . ?
C47 C42 C43 118.01(17) . . ?
C44 C43 C42 121.60(18) . . ?
C43 C44 C45 120.06(18) . . ?
C44 C45 C46 119.57(18) . . ?
C45 C46 C47 120.22(17) . . ?
C42 C47 C46 120.55(17) . . ?
C3A C2 C1 112.5(4) . . ?
C7A C2 C1 126.1(6) . . ?
C7A C2 C3A 121.0(7) . . ?
C3B C2 C1 127.1(4) . . ?
C3B C2 C7B 117.1(7) . . ?
C7B C2 C1 115.6(5) . . ?
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
N1 H1B N3 0.94(2) 2.00(2) 2.933(3) 172(2) .
N2 H2B N4 0.93(2) 2.12(2) 3.038(2) 168.9(17) .
_shelx_res_file
;
16srv262.res created by SHELXL-2014/7
TITL 16srv262 in P21/c #14
REM reset to P21/c #14
CELL 0.71073 21.212 11.2705 18.8494 90 114.8857 90
ZERR 4 0.0009 0.0005 0.0008 0 0.0016 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H B N O
UNIT 184 204 12 16 12
SADI C2 C3B C2 C7B C4B C3B C4A C3A C5A C4A C5B C4B C6B C5B C6A C5A C7A C6A =
C7B C6B C2 C3A C2 C7A
SADI C40B C35B C40A C35A C40B C39B C40A C39A C39B C38B C39A C38A C38B C37B =
C38A C37A C37A C36A C37B C36B C36B C35B C36A C35A
SADI C35B C34 C35A C34
RIGU
EADP C35B C35A
EADP C7A C7B
EADP C6A C6B
EADP C5A C5B
EADP C4A C4B
EADP C3A C3B
L.S. 7
PLAN 7
SIZE 0.128 0.164 0.294
TEMP -153.15
HTAB N2 N4
HTAB N1 N3
BOND
fmap 2
acta 52
OMIT -3 52
OMIT 1 1 0
REM
REM
REM
WGHT 0.038000 2.527000
EXTI 0.003861
FVAR 0.13224
O1 5 0.229594 0.751752 0.518536 11.00000 0.02989 0.03718 =
0.01986 -0.00872 0.01425 -0.01310
O2 5 0.278230 0.922067 0.478574 11.00000 0.02523 0.03241 =
0.01593 -0.00094 0.00902 -0.00505
O3 5 0.233065 0.759345 0.391006 11.00000 0.02290 0.03110 =
0.01711 -0.00166 0.00919 0.00224
N1 4 0.124948 0.709550 0.400847 11.00000 0.02098 0.04020 =
0.03059 -0.01544 0.01190 -0.00339
H1A 2 0.105633 0.675143 0.431664 11.00000 0.04572
H1B 2 0.114456 0.790624 0.399064 11.00000 0.04924
N2 4 0.356183 0.793983 0.584105 11.00000 0.02565 0.02748 =
0.01937 -0.00176 0.01218 -0.00523
H2A 2 0.360370 0.753651 0.544234 11.00000 0.03131
H2B 2 0.390008 0.853305 0.599698 11.00000 0.03581
C1 1 0.091153 0.661989 0.319849 11.00000 0.02306 0.05501 =
0.03164 -0.01877 0.00379 0.00412
AFIX 23
H1C 2 0.105891 0.578675 0.319717 11.00000 -1.20000
H1D 2 0.106867 0.708446 0.285701 11.00000 -1.20000
AFIX 0
PART 1
C3A 1 -0.014266 0.575128 0.315103 10.50000 0.02410 0.04163 =
0.06443 -0.00638 -0.00200 -0.00876
AFIX 43
H3A 2 0.015722 0.517140 0.349321 10.50000 -1.20000
AFIX 0
C4A 1 -0.085097 0.568264 0.293025 10.50000 0.02287 0.05853 =
0.08364 0.01138 -0.00319 -0.01224
AFIX 43
H4A 2 -0.104391 0.504078 0.309952 10.50000 -1.20000
AFIX 0
C5A 1 -0.126867 0.655403 0.246437 10.50000 0.01737 0.05715 =
0.06334 -0.00061 0.00385 -0.00376
AFIX 43
H5A 2 -0.175429 0.652161 0.232309 10.50000 -1.20000
AFIX 0
C6A 1 -0.100530 0.747883 0.219359 10.50000 0.02905 0.03980 =
0.05224 -0.00540 0.00539 0.00475
AFIX 43
H6A 2 -0.130962 0.805674 0.185429 10.50000 -1.20000
AFIX 0
C7A 1 -0.028315 0.756492 0.242144 10.50000 0.02636 0.03941 =
0.04563 -0.01452 0.00732 0.00174
AFIX 43
H7A 2 -0.008964 0.822268 0.226750 10.50000 -1.20000
AFIX 0
PART 0
PART 2
C3B 1 -0.029784 0.588369 0.301372 10.50000 0.02410 0.04163 =
0.06443 -0.00638 -0.00200 -0.00876
AFIX 43
H3B 2 -0.009831 0.523229 0.335483 10.50000 -1.20000
AFIX 0
C4B 1 -0.100113 0.601133 0.267925 10.50000 0.02287 0.05853 =
0.08364 0.01138 -0.00319 -0.01224
AFIX 43
H4B 2 -0.128133 0.546601 0.280322 10.50000 -1.20000
AFIX 0
C5B 1 -0.131115 0.692450 0.216208 10.50000 0.01737 0.05715 =
0.06334 -0.00061 0.00385 -0.00376
AFIX 43
H5B 2 -0.180301 0.699704 0.192639 10.50000 -1.20000
AFIX 0
C6B 1 -0.090772 0.773747 0.198464 10.50000 0.02905 0.03980 =
0.05224 -0.00540 0.00539 0.00475
AFIX 43
H6B 2 -0.111271 0.838909 0.164587 10.50000 -1.20000
AFIX 0
C7B 1 -0.018181 0.756100 0.232577 10.50000 0.02636 0.03941 =
0.04563 -0.01452 0.00732 0.00174
AFIX 43
H7B 2 0.010093 0.806601 0.217767 10.50000 -1.20000
AFIX 0
PART 0
C8 1 0.228594 0.556442 0.450251 11.00000 0.01877 0.03468 =
0.01412 -0.00372 0.00362 -0.00674
C9 1 0.206236 0.478452 0.492708 11.00000 0.04304 0.03963 =
0.02559 -0.01028 0.02040 -0.01543
AFIX 43
H9 2 0.178051 0.508430 0.516657 11.00000 -1.20000
AFIX 0
C10 1 0.223622 0.359252 0.501151 11.00000 0.06484 0.03808 =
0.03330 -0.00023 0.02651 -0.01797
AFIX 43
H10 2 0.207551 0.309217 0.530633 11.00000 -1.20000
AFIX 0
C11 1 0.264230 0.313088 0.466820 11.00000 0.06014 0.03308 =
0.03621 0.00612 0.01957 0.00085
AFIX 43
H11 2 0.276271 0.231343 0.472319 11.00000 -1.20000
AFIX 0
C12 1 0.287044 0.387030 0.424525 11.00000 0.04190 0.04040 =
0.03744 0.01148 0.02002 0.01401
AFIX 43
H12 2 0.315087 0.356296 0.400618 11.00000 -1.20000
AFIX 0
C13 1 0.269310 0.506349 0.416582 11.00000 0.02252 0.03621 =
0.02654 0.00846 0.01079 0.00313
AFIX 43
H13 2 0.285638 0.555653 0.386990 11.00000 -1.20000
AFIX 0
C14 1 0.369713 0.708445 0.648877 11.00000 0.03587 0.03684 =
0.02816 0.00780 0.01994 -0.00051
AFIX 23
H14A 2 0.330520 0.651734 0.633129 11.00000 -1.20000
H14B 2 0.371737 0.752199 0.695331 11.00000 -1.20000
AFIX 0
C15 1 0.436172 0.640353 0.670769 11.00000 0.03000 0.03286 =
0.02004 0.00531 0.01388 -0.00292
C16 1 0.435631 0.526356 0.642487 11.00000 0.03467 0.03556 =
0.02306 0.00257 0.01558 -0.00645
AFIX 43
H16 2 0.392657 0.490026 0.610153 11.00000 -1.20000
AFIX 0
C17 1 0.497152 0.465232 0.661000 11.00000 0.05117 0.03455 =
0.03535 0.00871 0.02760 0.00599
AFIX 43
H17 2 0.496208 0.387405 0.641222 11.00000 -1.20000
AFIX 0
C18 1 0.559904 0.517081 0.708147 11.00000 0.03610 0.05511 =
0.03740 0.01869 0.02038 0.01128
AFIX 43
H18 2 0.602136 0.475277 0.720621 11.00000 -1.20000
AFIX 0
C19 1 0.560942 0.629368 0.736902 11.00000 0.02970 0.05822 =
0.03135 0.00943 0.00846 -0.00526
AFIX 43
H19 2 0.604066 0.664913 0.769586 11.00000 -1.20000
AFIX 0
C20 1 0.499892 0.691002 0.718733 11.00000 0.04012 0.03647 =
0.02422 0.00047 0.01337 -0.00749
AFIX 43
H20 2 0.501308 0.768566 0.739079 11.00000 -1.20000
AFIX 0
C21 1 0.262310 0.930856 0.605773 11.00000 0.01564 0.03298 =
0.01620 -0.00258 0.00412 -0.00510
C22 1 0.243303 0.878383 0.660697 11.00000 0.06024 0.04153 =
0.04061 -0.01740 0.03569 -0.02598
AFIX 43
H22 2 0.240489 0.794326 0.661770 11.00000 -1.20000
AFIX 0
C23 1 0.228345 0.943756 0.713797 11.00000 0.06251 0.06064 =
0.04283 -0.02170 0.03956 -0.02985
AFIX 43
H23 2 0.216469 0.904565 0.751115 11.00000 -1.20000
AFIX 0
C24 1 0.230717 1.066308 0.712433 11.00000 0.02982 0.05525 =
0.02618 -0.01498 0.01232 -0.00066
AFIX 43
H24 2 0.219504 1.112006 0.747896 11.00000 -1.20000
AFIX 0
C25 1 0.249542 1.121219 0.659010 11.00000 0.04292 0.03441 =
0.02734 0.00000 0.00965 0.01310
AFIX 43
H25 2 0.251534 1.205347 0.657580 11.00000 -1.20000
AFIX 0
C26 1 0.265638 1.053688 0.607154 11.00000 0.03148 0.03400 =
0.02113 0.00547 0.01047 0.00774
AFIX 43
H26 2 0.279405 1.093121 0.571403 11.00000 -1.20000
AFIX 0
C27 1 0.268542 0.942734 0.340359 11.00000 0.02014 0.03587 =
0.02056 0.00532 0.01063 0.01128
C28 1 0.243147 0.897567 0.264424 11.00000 0.03032 0.03809 =
0.02199 0.00419 0.01168 0.01586
AFIX 43
H28 2 0.217532 0.825510 0.252515 11.00000 -1.20000
AFIX 0
C29 1 0.254539 0.955723 0.205978 11.00000 0.04885 0.04790 =
0.02105 0.01114 0.02013 0.02800
AFIX 43
H29 2 0.236244 0.923962 0.154528 11.00000 -1.20000
AFIX 0
C30 1 0.292320 1.059368 0.222496 11.00000 0.05706 0.04865 =
0.03589 0.02130 0.03389 0.02695
AFIX 43
H30 2 0.301108 1.097980 0.182764 11.00000 -1.20000
AFIX 0
C31 1 0.317564 1.107500 0.296999 11.00000 0.04776 0.04311 =
0.04039 0.01473 0.02756 0.00984
AFIX 43
H31 2 0.343196 1.179533 0.308527 11.00000 -1.20000
AFIX 0
C32 1 0.304902 1.049021 0.354701 11.00000 0.03247 0.04002 =
0.02455 0.00592 0.01497 0.00548
AFIX 43
H32 2 0.321660 1.082874 0.405505 11.00000 -1.20000
AFIX 0
B1 3 0.210306 0.696401 0.444095 11.00000 0.01890 0.03658 =
0.01815 -0.00576 0.00924 -0.00504
B2 3 0.275423 0.850798 0.542627 11.00000 0.02183 0.03309 =
0.01678 -0.00067 0.00836 -0.00544
B3 3 0.258842 0.871629 0.407294 11.00000 0.01414 0.03496 =
0.01886 0.00124 0.00621 0.00454
N3 4 0.101677 0.964338 0.410579 11.00000 0.03294 0.05874 =
0.09887 -0.03817 0.01779 0.00686
H3C 2 0.123934 1.011634 0.408956 11.00000 0.13434
H3D 2 0.127029 0.964201 0.467687 11.00000 0.12946
C34 1 0.034310 0.983438 0.408431 11.00000 0.05113 0.04258 =
0.05551 -0.00618 0.03476 0.00151
H34A 2 0.022674 0.920181 0.434058 11.00000 0.09620
H34B 2 -0.000097 0.970019 0.347797 11.00000 0.09117
PART 1
C35A 1 0.016055 1.101169 0.431506 10.70000 0.03831 0.03429 =
0.03623 0.00342 0.02347 0.00155
C36A 1 -0.052248 1.135440 0.403942 10.70000 0.04239 0.03339 =
0.03642 -0.00194 0.00433 0.00136
AFIX 43
H36A 2 -0.087599 1.084255 0.369849 10.70000 -1.20000
AFIX 0
C37A 1 -0.070384 1.243143 0.424991 10.70000 0.03822 0.03419 =
0.05845 0.00068 0.00947 0.01043
AFIX 43
H37A 2 -0.117901 1.265520 0.405332 10.70000 -1.20000
AFIX 0
C38A 1 -0.019971 1.317704 0.474151 10.70000 0.03813 0.02452 =
0.06054 -0.00525 0.02502 0.00072
AFIX 43
H38A 2 -0.032152 1.393415 0.486718 10.70000 -1.20000
AFIX 0
C39A 1 0.048092 1.282475 0.505079 10.70000 0.03593 0.04354 =
0.10166 -0.03131 0.03246 -0.01479
AFIX 43
H39A 2 0.083133 1.331395 0.541797 10.70000 -1.20000
AFIX 0
C40A 1 0.065561 1.174684 0.482392 10.70000 0.02905 0.04386 =
0.08417 -0.01586 0.02854 -0.00464
AFIX 43
H40A 2 0.113007 1.151652 0.502747 10.70000 -1.20000
AFIX 0
PART 0
PART 2
C35B 1 0.027826 1.103053 0.446883 10.30000 0.03831 0.03429 =
0.03623 0.00342 0.02347 0.00155
C36B 1 -0.031030 1.175888 0.404752 10.30000 0.05036
AFIX 43
H36B 2 -0.063230 1.151325 0.354235 10.30000 -1.20000
AFIX 0
C37B 1 -0.042960 1.281440 0.434930 10.30000 0.05336
AFIX 43
H37B 2 -0.083700 1.326734 0.406862 10.30000 -1.20000
AFIX 0
C38B 1 0.006378 1.319402 0.507540 10.30000 0.04399
AFIX 43
H38B 2 -0.000855 1.391668 0.528984 10.30000 -1.20000
AFIX 0
C39B 1 0.065350 1.253933 0.548625 10.30000 0.04532
AFIX 43
H39B 2 0.098855 1.281766 0.597556 10.30000 -1.20000
AFIX 0
C40B 1 0.075708 1.148080 0.518714 10.30000 0.03151
AFIX 43
H40B 2 0.116722 1.104000 0.547747 10.30000 -1.20000
AFIX 0
PART 0
N4 4 0.478110 0.963827 0.628881 11.00000 0.03893 0.03609 =
0.03853 0.00299 0.01727 -0.00192
H4C 2 0.498519 1.006928 0.681221 11.00000 0.08021
H4D 2 0.516608 0.929364 0.617372 11.00000 0.09098
C41 1 0.446797 1.051331 0.568836 11.00000 0.03170 0.04558 =
0.04509 0.00869 0.00955 -0.00152
AFIX 23
H41A 2 0.408328 1.088620 0.577436 11.00000 -1.20000
H41B 2 0.425690 1.009129 0.518129 11.00000 -1.20000
AFIX 0
C42 1 0.491933 1.150563 0.560544 11.00000 0.02722 0.03270 =
0.03385 0.00090 0.01424 0.00008
C43 1 0.462308 1.226916 0.497203 11.00000 0.03017 0.04482 =
0.03300 0.00400 0.00758 -0.00391
AFIX 43
H43 2 0.415402 1.214951 0.460990 11.00000 -1.20000
AFIX 0
C44 1 0.499209 1.319353 0.485651 11.00000 0.03606 0.04372 =
0.02918 0.00956 0.01156 0.00129
AFIX 43
H44 2 0.477867 1.369952 0.441631 11.00000 -1.20000
AFIX 0
C45 1 0.566996 1.338658 0.537755 11.00000 0.02878 0.03579 =
0.03350 0.00492 0.01922 -0.00068
AFIX 43
H45 2 0.592470 1.402957 0.530178 11.00000 -1.20000
AFIX 0
C46 1 0.597809 1.263939 0.601191 11.00000 0.02191 0.03786 =
0.03436 0.00236 0.01443 0.00404
AFIX 43
H46 2 0.644677 1.276732 0.637257 11.00000 -1.20000
AFIX 0
C47 1 0.560420 1.169994 0.612433 11.00000 0.03075 0.03209 =
0.03227 0.00888 0.01713 0.00917
AFIX 43
H47 2 0.582040 1.118757 0.656055 11.00000 -1.20000
AFIX 0
C2 1 0.013320 0.666905 0.287309 11.00000 0.02105 0.03096 =
0.04168 -0.01832 0.00545 -0.00195
HKLF 4
REM 16srv262 in P21/c #14
REM R1 = 0.0496 for 6020 Fo > 4sig(Fo) and 0.0740 for all 8022 data
REM 584 parameters refined using 604 restraints
END
WGHT 0.0382 2.5354
REM Highest difference peak 0.307, deepest hole -0.276, 1-sigma level 0.038
Q1 1 0.1893 0.9760 0.6832 11.00000 0.05 0.31
Q2 1 0.4995 1.0218 0.6028 11.00000 0.05 0.29
Q3 1 0.4292 1.0086 0.6068 11.00000 0.05 0.28
Q4 1 0.0688 0.9622 0.4493 11.00000 0.05 0.27
Q5 1 0.2016 0.9028 0.6413 11.00000 0.05 0.25
Q6 1 0.5275 1.1220 0.5757 11.00000 0.05 0.24
Q7 1 0.2174 0.6261 0.4457 11.00000 0.05 0.23
;
_shelx_res_checksum 12788
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_11c_16srv268
_database_code_depnum_ccdc_archive 'CCDC 1551623'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2016-07-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common ?
_chemical_name_systematic
'Di-2-chlorophenylboronic B-O-B di-2-phenylacetate '
_chemical_formula_moiety 'C28 H22 B2 Cl2 O5'
_chemical_formula_sum 'C28 H22 B2 Cl2 O5'
_chemical_formula_weight 530.97
_chemical_melting_point 429(4)
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'
O O 0.0106 0.0060 '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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.4296(5)
_cell_length_b 11.1470(6)
_cell_length_c 11.7996(6)
_cell_angle_alpha 84.748(2)
_cell_angle_beta 87.958(2)
_cell_angle_gamma 67.5356(19)
_cell_volume 1262.39(11)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9604
_cell_measurement_temperature 120
_cell_measurement_theta_max 33.17
_cell_measurement_theta_min 2.52
_shelx_estimated_absorpt_T_max 0.939
_shelx_estimated_absorpt_T_min 0.849
_exptl_absorpt_coefficient_mu 0.296
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9520
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1166 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9520.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.397
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 548
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.1360
0.00 -1.00 1.00 0.2100
1.00 0.00 0.00 0.1020
-1.00 0.00 0.00 0.1070
-1.00 1.00 0.00 0.1330
1.00 -1.00 0.00 0.1380
1.00 0.00 -1.00 0.1270
0.00 0.00 1.00 0.2850
1.00 -1.00 2.00 0.2000
0.00 0.00 -1.00 0.1440
1.00 -1.00 -2.00 0.1540
-1.00 -2.00 0.00 0.2500
1.00 2.00 0.00 0.1890
2.00 1.00 1.00 0.1970
-2.00 -2.00 -1.00 0.2160
_exptl_crystal_size_max 0.57
_exptl_crystal_size_mid 0.52
_exptl_crystal_size_min 0.214
_exptl_special_details
;
Data were collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of narrow-frame \w-scans (3 run
of 340 and one of 181 scans, scan width 0.5\%, 5s exposure), every run
at a different \f angle. Two runs of 358 \f-scans (scan width 1\%, 1s
exposure) were used for scaling overflowing intensities.
Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0295
_diffrn_reflns_av_unetI/netI 0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 28237
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full 33.199
_diffrn_reflns_theta_max 33.199
_diffrn_reflns_theta_min 2.522
_diffrn_ambient_temperature 120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'ImuS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 7311
_reflns_number_total 9620
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection 'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.475
_refine_diff_density_min -0.449
_refine_diff_density_rms 0.055
_refine_ls_extinction_coef .
_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 9620
_refine_ls_number_restraints 309
_refine_ls_R_factor_all 0.0637
_refine_ls_R_factor_gt 0.0427
_refine_ls_restrained_S_all 1.019
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.3420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1019
_refine_ls_wR_factor_ref 0.1111
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
All non-hydrogen atoms
with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
C14(H14A,H14B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26),
C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23660(3) 0.75897(3) 0.36266(3) 0.03314(8) Uani 1 1 d . U . . .
Cl2 Cl 0.85882(3) 0.18869(3) 0.32567(3) 0.02981(8) Uani 1 1 d . U . . .
O1 O 0.48929(7) 0.55912(7) 0.20218(6) 0.01613(14) Uani 1 1 d . U . . .
O2 O 0.33553(8) 0.46927(8) 0.30597(7) 0.02162(16) Uani 1 1 d . U . . .
O3 O 0.55829(8) 0.39482(8) 0.36060(7) 0.01941(15) Uani 1 1 d . U . . .
O4 O 0.38331(8) 0.43720(8) 0.10740(7) 0.02072(16) Uani 1 1 d . U . . .
O5 O 0.60273(8) 0.33096(7) 0.16740(7) 0.01899(15) Uani 1 1 d . U . . .
C1 C 0.22748(11) 0.66426(11) 0.15811(9) 0.0195(2) Uani 1 1 d . U . . .
C2 C 0.16614(12) 0.76530(12) 0.22840(11) 0.0247(2) Uani 1 1 d . U . . .
C3 C 0.04741(14) 0.87428(13) 0.19783(13) 0.0342(3) Uani 1 1 d . U . . .
H3 H 0.0084 0.9407 0.2483 0.041 Uiso 1 1 calc R . . . .
C4 C -0.01292(14) 0.88451(14) 0.09299(13) 0.0371(3) Uani 1 1 d . U . . .
H4 H -0.0940 0.9582 0.0712 0.045 Uiso 1 1 calc R . . . .
C5 C 0.04479(13) 0.78756(14) 0.01994(12) 0.0319(3) Uani 1 1 d . U . . .
H5 H 0.0043 0.7950 -0.0525 0.038 Uiso 1 1 calc R . . . .
C6 C 0.16258(12) 0.67903(12) 0.05304(10) 0.0235(2) Uani 1 1 d . U . . .
H6 H 0.2003 0.6125 0.0024 0.028 Uiso 1 1 calc R . . . .
C7 C 0.74938(11) 0.44375(11) 0.24135(9) 0.01771(19) Uani 1 1 d . U . . .
C8 C 0.87023(12) 0.33586(11) 0.27109(10) 0.0213(2) Uani 1 1 d . U . . .
C9 C 1.00247(12) 0.33825(14) 0.25907(11) 0.0284(3) Uani 1 1 d . U . . .
H9 H 1.0821 0.2628 0.2804 0.034 Uiso 1 1 calc R . . . .
C10 C 1.01604(13) 0.45232(15) 0.21546(12) 0.0322(3) Uani 1 1 d . U . . .
H10 H 1.1057 0.4550 0.2052 0.039 Uiso 1 1 calc R . . . .
C11 C 0.89935(13) 0.56266(14) 0.18675(11) 0.0289(3) Uani 1 1 d . U . . .
H11 H 0.9087 0.6413 0.1579 0.035 Uiso 1 1 calc R . . . .
C12 C 0.76834(12) 0.55776(12) 0.20030(10) 0.0218(2) Uani 1 1 d . U . . .
H12 H 0.6891 0.6343 0.1811 0.026 Uiso 1 1 calc R . . . .
C13 C 0.43057(11) 0.41610(11) 0.37988(9) 0.0195(2) Uani 1 1 d . U . . .
C14 C 0.39092(13) 0.37780(13) 0.49649(10) 0.0260(2) Uani 1 1 d . U . . .
H14A H 0.3389 0.4577 0.5349 0.031 Uiso 1 1 calc R . . . .
H14B H 0.4764 0.3280 0.5409 0.031 Uiso 1 1 calc R . . . .
C15 C 0.30339(11) 0.29643(11) 0.49699(9) 0.0195(2) Uani 1 1 d . U . . .
C16 C 0.16917(12) 0.34452(14) 0.53979(10) 0.0265(2) Uani 1 1 d . U . . .
H16 H 0.1307 0.4305 0.5631 0.032 Uiso 1 1 calc R . . . .
C17 C 0.09131(15) 0.26766(18) 0.54859(12) 0.0398(3) Uani 1 1 d . U . . .
H17 H -0.0001 0.3008 0.5786 0.048 Uiso 1 1 calc R . . . .
C18 C 0.14560(19) 0.14362(18) 0.51408(13) 0.0452(4) Uani 1 1 d . U . . .
H18 H 0.0924 0.0906 0.5216 0.054 Uiso 1 1 calc R . . . .
C19 C 0.2774(2) 0.09597(15) 0.46853(12) 0.0416(4) Uani 1 1 d . U . . .
H19 H 0.3139 0.0110 0.4430 0.050 Uiso 1 1 calc R . . . .
C20 C 0.35728(15) 0.17219(13) 0.45987(11) 0.0297(3) Uani 1 1 d . U . . .
H20 H 0.4482 0.1392 0.4287 0.036 Uiso 1 1 calc R . . . .
C21 C 0.50086(12) 0.34295(10) 0.10548(9) 0.01874(19) Uani 1 1 d . U . . .
C22 C 0.51861(14) 0.23640(11) 0.03089(10) 0.0232(2) Uani 1 1 d . U . . .
H22A H 0.6128 0.2058 -0.0027 0.028 Uiso 1 1 calc R . . . .
H22B H 0.4502 0.2692 -0.0319 0.028 Uiso 1 1 calc R . . . .
C23 C 0.49745(11) 0.12506(10) 0.10170(9) 0.01796(19) Uani 1 1 d . U . . .
C24 C 0.37226(13) 0.10818(12) 0.09790(11) 0.0264(2) Uani 1 1 d . U . . .
H24 H 0.2979 0.1686 0.0528 0.032 Uiso 1 1 calc R . . . .
C25 C 0.35627(16) 0.00285(15) 0.16011(13) 0.0368(3) Uani 1 1 d . U . . .
H25 H 0.2707 -0.0086 0.1576 0.044 Uiso 1 1 calc R . . . .
C26 C 0.46422(18) -0.08551(14) 0.22572(12) 0.0380(3) Uani 1 1 d . U . . .
H26 H 0.4535 -0.1586 0.2665 0.046 Uiso 1 1 calc R . . . .
C27 C 0.58745(16) -0.06772(13) 0.23211(11) 0.0324(3) Uani 1 1 d . U . . .
H27 H 0.6610 -0.1277 0.2782 0.039 Uiso 1 1 calc R . . . .
C28 C 0.60373(12) 0.03794(11) 0.17107(10) 0.0233(2) Uani 1 1 d . U . . .
H28 H 0.6881 0.0510 0.1766 0.028 Uiso 1 1 calc R . . . .
B1 B 0.36421(12) 0.54045(12) 0.19261(10) 0.0178(2) Uani 1 1 d . U . . .
B2 B 0.59761(12) 0.44246(11) 0.24124(10) 0.0167(2) Uani 1 1 d . U . . .
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
Cl1 0.03260(16) 0.04202(18) 0.03411(16) -0.01870(13) 0.01167(12) -0.02213(14)
Cl2 0.02811(15) 0.02000(13) 0.03872(17) 0.00180(11) -0.00199(12) -0.00704(11)
O1 0.0174(3) 0.0152(3) 0.0185(3) -0.0022(3) 0.0027(3) -0.0093(3)
O2 0.0220(4) 0.0283(4) 0.0200(4) 0.0036(3) -0.0015(3) -0.0168(3)
O3 0.0206(4) 0.0239(4) 0.0177(4) 0.0003(3) 0.0002(3) -0.0133(3)
O4 0.0243(4) 0.0177(4) 0.0225(4) -0.0018(3) -0.0042(3) -0.0101(3)
O5 0.0216(4) 0.0164(3) 0.0211(4) -0.0030(3) -0.0003(3) -0.0092(3)
C1 0.0194(5) 0.0191(5) 0.0220(5) 0.0001(4) 0.0052(4) -0.0105(4)
C2 0.0248(5) 0.0243(5) 0.0286(6) -0.0048(4) 0.0099(4) -0.0135(4)
C3 0.0320(6) 0.0229(6) 0.0442(8) -0.0047(5) 0.0186(6) -0.0076(5)
C4 0.0268(6) 0.0275(6) 0.0447(8) 0.0100(6) 0.0121(6) -0.0006(5)
C5 0.0239(6) 0.0345(7) 0.0289(6) 0.0105(5) 0.0040(5) -0.0051(5)
C6 0.0208(5) 0.0249(5) 0.0228(5) 0.0024(4) 0.0040(4) -0.0078(4)
C7 0.0188(5) 0.0210(5) 0.0161(4) -0.0031(4) 0.0016(3) -0.0104(4)
C8 0.0207(5) 0.0233(5) 0.0207(5) -0.0016(4) 0.0011(4) -0.0096(4)
C9 0.0192(5) 0.0365(7) 0.0280(6) 0.0000(5) -0.0001(4) -0.0095(5)
C10 0.0218(5) 0.0493(8) 0.0315(6) 0.0002(6) 0.0018(5) -0.0210(6)
C11 0.0289(6) 0.0380(7) 0.0283(6) 0.0031(5) 0.0002(5) -0.0235(5)
C12 0.0232(5) 0.0255(5) 0.0210(5) 0.0001(4) -0.0001(4) -0.0143(4)
C13 0.0233(5) 0.0242(5) 0.0176(5) -0.0021(4) 0.0005(4) -0.0164(4)
C14 0.0308(6) 0.0406(7) 0.0160(5) 0.0008(5) -0.0002(4) -0.0248(5)
C15 0.0220(5) 0.0267(5) 0.0133(4) 0.0024(4) 0.0001(4) -0.0143(4)
C16 0.0232(5) 0.0368(7) 0.0205(5) 0.0027(5) 0.0017(4) -0.0137(5)
C17 0.0312(7) 0.0656(10) 0.0317(7) 0.0119(7) -0.0019(5) -0.0322(7)
C18 0.0633(10) 0.0630(10) 0.0320(7) 0.0172(7) -0.0160(7) -0.0526(9)
C19 0.0738(11) 0.0316(7) 0.0278(7) 0.0036(5) -0.0115(7) -0.0298(7)
C20 0.0368(7) 0.0296(6) 0.0225(6) -0.0014(5) 0.0018(5) -0.0128(5)
C21 0.0263(5) 0.0168(5) 0.0162(4) -0.0001(4) 0.0008(4) -0.0121(4)
C22 0.0378(6) 0.0190(5) 0.0166(5) -0.0031(4) 0.0000(4) -0.0148(5)
C23 0.0237(5) 0.0153(4) 0.0169(4) -0.0043(4) 0.0019(4) -0.0092(4)
C24 0.0243(5) 0.0273(6) 0.0310(6) -0.0093(5) 0.0010(5) -0.0121(5)
C25 0.0406(7) 0.0407(8) 0.0434(8) -0.0159(6) 0.0150(6) -0.0299(6)
C26 0.0646(10) 0.0284(6) 0.0302(7) -0.0046(5) 0.0160(6) -0.0288(7)
C27 0.0482(8) 0.0218(6) 0.0230(6) 0.0011(5) 0.0007(5) -0.0093(5)
C28 0.0256(5) 0.0218(5) 0.0220(5) -0.0020(4) 0.0002(4) -0.0086(4)
B1 0.0201(5) 0.0181(5) 0.0183(5) -0.0010(4) 0.0013(4) -0.0110(4)
B2 0.0198(5) 0.0171(5) 0.0163(5) -0.0024(4) 0.0021(4) -0.0104(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
Cl1 C2 1.7543(13) . ?
Cl2 C8 1.7523(12) . ?
O1 B1 1.4072(13) . ?
O1 B2 1.4087(14) . ?
O2 C13 1.2698(14) . ?
O2 B1 1.5705(14) . ?
O3 C13 1.2764(13) . ?
O3 B2 1.5563(14) . ?
O4 C21 1.2749(14) . ?
O4 B1 1.5485(14) . ?
O5 C21 1.2687(13) . ?
O5 B2 1.5655(14) . ?
C1 C2 1.3958(16) . ?
C1 C6 1.3998(17) . ?
C1 B1 1.5933(17) . ?
C2 C3 1.3933(19) . ?
C3 C4 1.383(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.3919(17) . ?
C7 C8 1.3979(16) . ?
C7 C12 1.4005(15) . ?
C7 B2 1.5886(16) . ?
C8 C9 1.3916(16) . ?
C9 C10 1.3835(19) . ?
C10 C11 1.385(2) . ?
C11 C12 1.3912(16) . ?
C13 C14 1.4945(15) . ?
C14 C15 1.5125(15) . ?
C15 C16 1.3884(16) . ?
C15 C20 1.3872(18) . ?
C16 C17 1.3834(19) . ?
C17 C18 1.373(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.395(2) . ?
C21 C22 1.4938(15) . ?
C22 C23 1.5143(15) . ?
C23 C24 1.3913(16) . ?
C23 C28 1.3922(16) . ?
C24 C25 1.3887(19) . ?
C25 C26 1.383(2) . ?
C26 C27 1.379(2) . ?
C27 C28 1.3869(18) . ?
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
B1 O1 B2 111.23(8) . . ?
C13 O2 B1 120.41(8) . . ?
C13 O3 B2 117.69(9) . . ?
C21 O4 B1 117.51(9) . . ?
C21 O5 B2 121.07(9) . . ?
C2 C1 C6 115.74(11) . . ?
C2 C1 B1 122.90(11) . . ?
C6 C1 B1 121.36(10) . . ?
C1 C2 Cl1 120.46(10) . . ?
C3 C2 Cl1 116.57(10) . . ?
C3 C2 C1 122.96(12) . . ?
C4 C3 C2 119.16(12) . . ?
C5 C4 C3 120.02(12) . . ?
C4 C5 C6 119.67(13) . . ?
C5 C6 C1 122.44(12) . . ?
C8 C7 C12 115.83(10) . . ?
C8 C7 B2 125.13(10) . . ?
C12 C7 B2 118.83(10) . . ?
C7 C8 Cl2 119.80(8) . . ?
C9 C8 Cl2 117.08(9) . . ?
C9 C8 C7 123.12(11) . . ?
C10 C9 C8 118.88(12) . . ?
C9 C10 C11 120.22(11) . . ?
C10 C11 C12 119.68(12) . . ?
C11 C12 C7 122.23(11) . . ?
O2 C13 O3 123.64(10) . . ?
O2 C13 C14 118.39(10) . . ?
O3 C13 C14 117.97(10) . . ?
C13 C14 C15 113.62(9) . . ?
C16 C15 C14 119.51(11) . . ?
C20 C15 C14 120.94(11) . . ?
C20 C15 C16 119.48(11) . . ?
C17 C16 C15 120.25(13) . . ?
C18 C17 C16 120.31(14) . . ?
C17 C18 C19 120.01(13) . . ?
C18 C19 C20 120.22(14) . . ?
C15 C20 C19 119.69(13) . . ?
O4 C21 C22 118.63(10) . . ?
O5 C21 O4 123.74(10) . . ?
O5 C21 C22 117.55(10) . . ?
C21 C22 C23 108.87(9) . . ?
C24 C23 C22 120.56(11) . . ?
C24 C23 C28 119.25(11) . . ?
C28 C23 C22 120.19(10) . . ?
C25 C24 C23 119.86(12) . . ?
C26 C25 C24 120.34(12) . . ?
C27 C26 C25 120.14(12) . . ?
C26 C27 C28 119.83(13) . . ?
C27 C28 C23 120.52(12) . . ?
O1 B1 O2 109.71(9) . . ?
O1 B1 O4 109.52(9) . . ?
O1 B1 C1 118.29(9) . . ?
O2 B1 C1 108.73(8) . . ?
O4 B1 O2 101.09(8) . . ?
O4 B1 C1 108.11(9) . . ?
O1 B2 O3 108.92(8) . . ?
O1 B2 O5 109.31(9) . . ?
O1 B2 C7 117.01(9) . . ?
O3 B2 O5 102.02(8) . . ?
O3 B2 C7 111.28(9) . . ?
O5 B2 C7 107.22(8) . . ?
_shelx_SHELXL_version_number 2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
16srv268.res created by SHELXL-2014/7
TITL 16srv268 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 10.4296 11.147 11.7996 84.7482 87.9581 67.5356
ZERR 2 0.0005 0.0006 0.0006 0.0021 0.0021 0.0019
LATT 1
SFAC C H B O Cl
UNIT 56 44 4 10 4
RIGU
L.S. 7
PLAN 7
SIZE 0.214 0.52 0.57
TEMP -153.15
BOND
fmap 2
acta 66.4
OMIT 0 1 0
OMIT 1 0 0
REM
REM
REM
WGHT 0.051000 0.342000
FVAR 0.33678
CL1 5 0.236596 0.758972 0.362659 11.00000 0.03260 0.04202 =
0.03411 -0.01870 0.01167 -0.02213
CL2 5 0.858820 0.188690 0.325670 11.00000 0.02811 0.02000 =
0.03872 0.00180 -0.00199 -0.00704
O1 4 0.489289 0.559122 0.202177 11.00000 0.01741 0.01523 =
0.01845 -0.00218 0.00271 -0.00930
O2 4 0.335530 0.469273 0.305969 11.00000 0.02203 0.02832 =
0.01995 0.00358 -0.00148 -0.01678
O3 4 0.558288 0.394820 0.360597 11.00000 0.02057 0.02387 =
0.01770 0.00032 0.00017 -0.01328
O4 4 0.383306 0.437195 0.107400 11.00000 0.02428 0.01768 =
0.02246 -0.00182 -0.00424 -0.01011
O5 4 0.602733 0.330955 0.167403 11.00000 0.02161 0.01639 =
0.02107 -0.00297 -0.00029 -0.00925
C1 1 0.227476 0.664262 0.158109 11.00000 0.01937 0.01913 =
0.02203 0.00011 0.00525 -0.01053
C2 1 0.166136 0.765301 0.228396 11.00000 0.02484 0.02429 =
0.02861 -0.00482 0.00987 -0.01352
C3 1 0.047408 0.874283 0.197829 11.00000 0.03198 0.02293 =
0.04417 -0.00473 0.01863 -0.00759
AFIX 43
H3 2 0.008376 0.940726 0.248334 11.00000 -1.20000
AFIX 0
C4 1 -0.012920 0.884509 0.092994 11.00000 0.02680 0.02753 =
0.04474 0.00999 0.01211 -0.00063
AFIX 43
H4 2 -0.094050 0.958206 0.071216 11.00000 -1.20000
AFIX 0
C5 1 0.044791 0.787562 0.019942 11.00000 0.02393 0.03454 =
0.02895 0.01048 0.00401 -0.00511
AFIX 43
H5 2 0.004269 0.794955 -0.052509 11.00000 -1.20000
AFIX 0
C6 1 0.162582 0.679030 0.053041 11.00000 0.02081 0.02492 =
0.02285 0.00240 0.00401 -0.00780
AFIX 43
H6 2 0.200340 0.612505 0.002447 11.00000 -1.20000
AFIX 0
C7 1 0.749380 0.443751 0.241346 11.00000 0.01884 0.02097 =
0.01607 -0.00308 0.00160 -0.01044
C8 1 0.870231 0.335857 0.271091 11.00000 0.02072 0.02335 =
0.02073 -0.00164 0.00112 -0.00959
C9 1 1.002466 0.338253 0.259067 11.00000 0.01923 0.03651 =
0.02805 0.00004 -0.00013 -0.00953
AFIX 43
H9 2 1.082081 0.262832 0.280438 11.00000 -1.20000
AFIX 0
C10 1 1.016042 0.452322 0.215464 11.00000 0.02176 0.04926 =
0.03154 0.00024 0.00176 -0.02098
AFIX 43
H10 2 1.105710 0.454965 0.205187 11.00000 -1.20000
AFIX 0
C11 1 0.899351 0.562663 0.186748 11.00000 0.02891 0.03801 =
0.02826 0.00310 0.00023 -0.02353
AFIX 43
H11 2 0.908720 0.641323 0.157933 11.00000 -1.20000
AFIX 0
C12 1 0.768344 0.557760 0.200302 11.00000 0.02316 0.02552 =
0.02102 0.00008 -0.00009 -0.01434
AFIX 43
H12 2 0.689060 0.634345 0.181065 11.00000 -1.20000
AFIX 0
C13 1 0.430565 0.416096 0.379876 11.00000 0.02330 0.02421 =
0.01761 -0.00210 0.00048 -0.01639
C14 1 0.390924 0.377796 0.496491 11.00000 0.03078 0.04057 =
0.01601 0.00079 -0.00022 -0.02476
AFIX 23
H14A 2 0.338870 0.457655 0.534945 11.00000 -1.20000
H14B 2 0.476423 0.327992 0.540936 11.00000 -1.20000
AFIX 0
C15 1 0.303393 0.296429 0.496990 11.00000 0.02201 0.02673 =
0.01333 0.00243 0.00013 -0.01434
C16 1 0.169175 0.344518 0.539791 11.00000 0.02317 0.03680 =
0.02051 0.00269 0.00175 -0.01366
AFIX 43
H16 2 0.130665 0.430528 0.563126 11.00000 -1.20000
AFIX 0
C17 1 0.091310 0.267661 0.548585 11.00000 0.03123 0.06562 =
0.03171 0.01189 -0.00191 -0.03216
AFIX 43
H17 2 -0.000141 0.300831 0.578628 11.00000 -1.20000
AFIX 0
C18 1 0.145600 0.143623 0.514084 11.00000 0.06333 0.06299 =
0.03199 0.01722 -0.01596 -0.05257
AFIX 43
H18 2 0.092360 0.090641 0.521598 11.00000 -1.20000
AFIX 0
C19 1 0.277406 0.095970 0.468529 11.00000 0.07383 0.03164 =
0.02779 0.00357 -0.01153 -0.02984
AFIX 43
H19 2 0.313903 0.010952 0.442963 11.00000 -1.20000
AFIX 0
C20 1 0.357280 0.172188 0.459875 11.00000 0.03678 0.02959 =
0.02246 -0.00138 0.00184 -0.01284
AFIX 43
H20 2 0.448164 0.139175 0.428709 11.00000 -1.20000
AFIX 0
C21 1 0.500858 0.342949 0.105476 11.00000 0.02631 0.01682 =
0.01621 -0.00006 0.00085 -0.01207
C22 1 0.518608 0.236396 0.030887 11.00000 0.03777 0.01903 =
0.01658 -0.00313 -0.00004 -0.01477
AFIX 23
H22A 2 0.612818 0.205777 -0.002740 11.00000 -1.20000
H22B 2 0.450167 0.269195 -0.031863 11.00000 -1.20000
AFIX 0
C23 1 0.497454 0.125063 0.101697 11.00000 0.02367 0.01530 =
0.01693 -0.00430 0.00185 -0.00920
C24 1 0.372259 0.108185 0.097898 11.00000 0.02428 0.02732 =
0.03100 -0.00927 0.00099 -0.01209
AFIX 43
H24 2 0.297877 0.168587 0.052842 11.00000 -1.20000
AFIX 0
C25 1 0.356266 0.002850 0.160113 11.00000 0.04059 0.04068 =
0.04342 -0.01585 0.01501 -0.02991
AFIX 43
H25 2 0.270718 -0.008564 0.157584 11.00000 -1.20000
AFIX 0
C26 1 0.464217 -0.085508 0.225724 11.00000 0.06458 0.02839 =
0.03016 -0.00462 0.01600 -0.02878
AFIX 43
H26 2 0.453456 -0.158624 0.266488 11.00000 -1.20000
AFIX 0
C27 1 0.587451 -0.067716 0.232107 11.00000 0.04816 0.02176 =
0.02299 0.00113 0.00067 -0.00927
AFIX 43
H27 2 0.661016 -0.127680 0.278198 11.00000 -1.20000
AFIX 0
C28 1 0.603732 0.037941 0.171071 11.00000 0.02565 0.02176 =
0.02197 -0.00202 0.00019 -0.00856
AFIX 43
H28 2 0.688064 0.050968 0.176643 11.00000 -1.20000
AFIX 0
B1 3 0.364208 0.540448 0.192615 11.00000 0.02007 0.01814 =
0.01829 -0.00097 0.00128 -0.01096
B2 3 0.597606 0.442457 0.241235 11.00000 0.01981 0.01711 =
0.01633 -0.00244 0.00214 -0.01035
HKLF 4
REM 16srv268 in P-1 #2
REM R1 = 0.0427 for 7311 Fo > 4sig(Fo) and 0.0637 for all 9620 data
REM 334 parameters refined using 309 restraints
END
WGHT 0.0507 0.3402
REM Highest difference peak 0.475, deepest hole -0.449, 1-sigma level 0.055
Q1 1 0.6774 0.4381 0.2491 11.00000 0.05 0.48
Q2 1 0.2963 0.6083 0.1851 11.00000 0.05 0.42
Q3 1 0.2386 0.3221 0.5145 11.00000 0.05 0.41
Q4 1 0.9371 0.3370 0.2750 11.00000 0.05 0.37
Q5 1 0.0981 0.7328 0.0441 11.00000 0.05 0.35
Q6 1 0.4354 0.1166 0.1125 11.00000 0.05 0.35
Q7 1 0.1814 0.6833 0.1090 11.00000 0.05 0.35
REM The information below was added by Olex2.
REM
REM R1 = 0.0427 for 7311 Fo > 4sig(Fo) and 0.0637 for all 28239 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.48, deepest hole -0.45
REM Mean Shift 0, Max Shift 0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0637
REM R1_gt = 0.0427
REM wR_ref = 0.1111
REM GOOF = 1.027
REM Shift_max = 0.001
REM Shift_mean = 0
REM Reflections_all = 28239
REM Reflections_gt = 7311
REM Parameters = n/a
REM Hole = -0.45
REM Peak = 0.48
REM Flack = n/a
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_10c_15srv282
_database_code_depnum_ccdc_archive 'CCDC 1551621'
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2015-11-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common ?
_chemical_name_systematic
; phenylboroxine complex with 2 equiv. benzylamine
;
_chemical_formula_moiety 'C25 H24 B3 N O3, C7 H9 N'
_chemical_formula_sum 'C32 H33 B3 N2 O3'
_chemical_formula_weight 526.03
_chemical_melting_point ?
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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 11.2396(4)
_cell_length_b 15.2054(6)
_cell_length_c 17.9361(7)
_cell_angle_alpha 89.7333(16)
_cell_angle_beta 72.0196(15)
_cell_angle_gamma 84.3291(17)
_cell_volume 2900.27(19)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9200
_cell_measurement_temperature 120
_cell_measurement_theta_max 27.53
_cell_measurement_theta_min 2.25
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.075
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8866
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1546 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8866.
The \l/2 correction factor is Not present.
;
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 -1.00 0.1000
1.00 0.00 1.00 0.0810
0.00 0.00 1.00 0.1350
0.00 0.00 -1.00 0.1710
-1.00 0.00 2.00 0.1630
0.00 -1.00 -1.00 0.3190
0.00 1.00 1.00 0.2900
-1.00 -2.00 1.00 0.2320
1.00 2.00 -1.00 0.2180
1.00 2.00 0.00 0.2370
2.00 0.00 -1.00 0.1660
0.00 -1.00 0.00 0.3370
0.00 -1.00 1.00 0.2130
0.00 2.00 -1.00 0.2530
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.205
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description trapezoid
_exptl_crystal_F_000 1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: benzylamine, toluene'
_exptl_crystal_size_max 0.683
_exptl_crystal_size_mid 0.379
_exptl_crystal_size_min 0.2
_exptl_special_details
; Data were collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of narrow-frame \w-scans (scan
width 0.5\%, 5s exposure), every run at a different \f angle.
Two runs of \f-scans (scan width 1\%, 1s exposure) were used for
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0439
_diffrn_reflns_av_unetI/netI 0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 55370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.578
_diffrn_reflns_theta_min 2.247
_diffrn_ambient_temperature 120
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'ImuS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 10461
_reflns_number_total 13416
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.332
_refine_diff_density_min -0.293
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.030
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 753
_refine_ls_number_reflns 13416
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0624
_refine_ls_R_factor_gt 0.0445
_refine_ls_restrained_S_all 1.030
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.9460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1005
_refine_ls_wR_factor_ref 0.1087
_refine_special_details
; Amino H atoms - refall, other H - riding (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C1(H1C,H1D), C33(H33A,H33B), C26(H26A,H26B), C58(H58A,H58B)
2.b Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
C23(H23), C24(H24), C25(H25), C35(H35), C36(H36), C37(H37), C38(H38),
C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
C49(H49), C50(H50), C51(H51), C53(H53), C54(H54), C55(H55), C56(H56),
C57(H57), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C60(H60), C61(H61),
C62(H62), C63(H63), C64(H64)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44951(8) 0.11540(6) 0.76979(5) 0.02017(19) Uani 1 1 d . . . . .
O2 O 0.30947(8) 0.09005(6) 0.69721(5) 0.0229(2) Uani 1 1 d . . . . .
O3 O 0.23983(8) 0.19492(6) 0.80409(5) 0.02035(19) Uani 1 1 d . . . . .
N1 N 0.30586(10) 0.11138(7) 0.90239(7) 0.0192(2) Uani 1 1 d . . . . .
H1A H 0.2796(14) 0.0625(11) 0.8823(9) 0.027(4) Uiso 1 1 d . . . . .
H1B H 0.2359(15) 0.1399(10) 0.9375(9) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.39910(12) 0.08048(9) 0.94306(8) 0.0250(3) Uani 1 1 d . . . . .
H1C H 0.4194 0.1314 0.9694 0.030 Uiso 1 1 calc R . . . .
H1D H 0.4776 0.0540 0.9042 0.030 Uiso 1 1 calc R . . . .
C2 C 0.34665(11) 0.01303(9) 1.00274(8) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.36033(13) -0.07599(9) 0.98160(8) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.4100 -0.0955 0.9302 0.032 Uiso 1 1 calc R . . . .
C4 C 0.30211(14) -0.13669(10) 1.03503(10) 0.0333(3) Uani 1 1 d . . . . .
H4 H 0.3111 -0.1974 1.0199 0.040 Uiso 1 1 calc R . . . .
C5 C 0.23107(14) -0.10918(10) 1.11022(9) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.1900 -0.1506 1.1465 0.041 Uiso 1 1 calc R . . . .
C6 C 0.21993(14) -0.02141(11) 1.13245(9) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.1729 -0.0025 1.1845 0.041 Uiso 1 1 calc R . . . .
C7 C 0.27730(13) 0.03943(9) 1.07889(8) 0.0274(3) Uani 1 1 d . . . . .
H7 H 0.2690 0.0999 1.0946 0.033 Uiso 1 1 calc R . . . .
C8 C 0.40521(11) 0.26053(8) 0.84958(7) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.53055(12) 0.26300(9) 0.84584(8) 0.0219(3) Uani 1 1 d . . . . .
H9 H 0.5871 0.2108 0.8306 0.026 Uiso 1 1 calc R . . . .
C10 C 0.57509(12) 0.33940(9) 0.86374(8) 0.0261(3) Uani 1 1 d . . . . .
H10 H 0.6608 0.3388 0.8613 0.031 Uiso 1 1 calc R . . . .
C11 C 0.49498(13) 0.41648(9) 0.88515(8) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.5254 0.4690 0.8971 0.032 Uiso 1 1 calc R . . . .
C12 C 0.36986(13) 0.41630(9) 0.88906(9) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.3142 0.4690 0.9034 0.033 Uiso 1 1 calc R . . . .
C13 C 0.32622(12) 0.33917(9) 0.87200(8) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.2400 0.3397 0.8757 0.028 Uiso 1 1 calc R . . . .
C14 C 0.52891(12) 0.00474(8) 0.65767(8) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.64195(13) -0.01582(10) 0.67421(9) 0.0296(3) Uani 1 1 d . . . . .
H15 H 0.6549 0.0125 0.7178 0.035 Uiso 1 1 calc R . . . .
C16 C 0.73565(14) -0.07677(10) 0.62823(9) 0.0358(4) Uani 1 1 d . . . . .
H16 H 0.8119 -0.0899 0.6404 0.043 Uiso 1 1 calc R . . . .
C17 C 0.71780(14) -0.11835(10) 0.56465(10) 0.0356(4) Uani 1 1 d . . . . .
H17 H 0.7818 -0.1602 0.5332 0.043 Uiso 1 1 calc R . . . .
C18 C 0.60731(15) -0.09916(10) 0.54684(10) 0.0355(3) Uani 1 1 d . . . . .
H18 H 0.5952 -0.1276 0.5031 0.043 Uiso 1 1 calc R . . . .
C19 C 0.51390(13) -0.03814(9) 0.59312(9) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.4380 -0.0253 0.5805 0.034 Uiso 1 1 calc R . . . .
C20 C 0.09126(12) 0.17675(9) 0.72747(7) 0.0214(3) Uani 1 1 d . . . . .
C21 C 0.04325(14) 0.11956(11) 0.68632(8) 0.0326(3) Uani 1 1 d . . . . .
H21 H 0.0902 0.0648 0.6661 0.039 Uiso 1 1 calc R . . . .
C22 C -0.07281(15) 0.14151(13) 0.67439(9) 0.0419(4) Uani 1 1 d . . . . .
H22 H -0.1054 0.1010 0.6476 0.050 Uiso 1 1 calc R . . . .
C23 C -0.14025(14) 0.22188(13) 0.70143(9) 0.0409(4) Uani 1 1 d . . . . .
H23 H -0.2180 0.2377 0.6917 0.049 Uiso 1 1 calc R . . . .
C24 C -0.09473(13) 0.27910(11) 0.74246(9) 0.0345(4) Uani 1 1 d . . . . .
H24 H -0.1414 0.3344 0.7614 0.041 Uiso 1 1 calc R . . . .
C25 C 0.01897(12) 0.25653(9) 0.75641(8) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.0482 0.2960 0.7862 0.031 Uiso 1 1 calc R . . . .
B1 B 0.35354(13) 0.17359(9) 0.82660(8) 0.0182(3) Uani 1 1 d . . . . .
B2 B 0.42500(13) 0.07360(10) 0.71107(9) 0.0205(3) Uani 1 1 d . . . . .
B3 B 0.22030(13) 0.15324(9) 0.74368(8) 0.0198(3) Uani 1 1 d . . . . .
O4 O 0.13359(8) 0.63390(6) 0.69643(5) 0.01979(19) Uani 1 1 d . . . . .
O5 O 0.27133(8) 0.73073(6) 0.72213(5) 0.0233(2) Uani 1 1 d . . . . .
O6 O 0.23949(8) 0.59923(6) 0.79503(5) 0.01988(19) Uani 1 1 d . . . . .
N3 N 0.23366(10) 0.48315(7) 0.70021(7) 0.0195(2) Uani 1 1 d . . . . .
H3A H 0.2431(14) 0.4389(11) 0.7330(9) 0.029(4) Uiso 1 1 d . . . . .
H3B H 0.1839(17) 0.4625(11) 0.6721(10) 0.042(5) Uiso 1 1 d . . . . .
C33 C 0.35936(12) 0.49463(9) 0.64291(8) 0.0250(3) Uani 1 1 d . . . . .
H33A H 0.4100 0.5242 0.6697 0.030 Uiso 1 1 calc R . . . .
H33B H 0.3480 0.5331 0.6004 0.030 Uiso 1 1 calc R . . . .
C34 C 0.42879(11) 0.40726(8) 0.60801(8) 0.0208(3) Uani 1 1 d . . . . .
C35 C 0.45377(12) 0.38617(9) 0.52910(8) 0.0247(3) Uani 1 1 d . . . . .
H35 H 0.4258 0.4269 0.4962 0.030 Uiso 1 1 calc R . . . .
C36 C 0.51954(14) 0.30564(10) 0.49802(9) 0.0317(3) Uani 1 1 d . . . . .
H36 H 0.5368 0.2916 0.4439 0.038 Uiso 1 1 calc R . . . .
C37 C 0.55994(13) 0.24591(9) 0.54573(9) 0.0312(3) Uani 1 1 d . . . . .
H37 H 0.6053 0.1910 0.5243 0.037 Uiso 1 1 calc R . . . .
C38 C 0.53428(12) 0.26615(9) 0.62443(9) 0.0281(3) Uani 1 1 d . . . . .
H38 H 0.5610 0.2248 0.6573 0.034 Uiso 1 1 calc R . . . .
C39 C 0.46986(12) 0.34639(9) 0.65534(8) 0.0247(3) Uani 1 1 d . . . . .
H39 H 0.4534 0.3603 0.7094 0.030 Uiso 1 1 calc R . . . .
C40 C 0.02980(11) 0.53579(8) 0.80993(7) 0.0178(2) Uani 1 1 d . . . . .
C41 C 0.02809(12) 0.49216(8) 0.87895(7) 0.0212(3) Uani 1 1 d . . . . .
H41 H 0.1035 0.4832 0.8926 0.025 Uiso 1 1 calc R . . . .
C42 C -0.08052(13) 0.46146(9) 0.92819(8) 0.0248(3) Uani 1 1 d . . . . .
H42 H -0.0787 0.4318 0.9746 0.030 Uiso 1 1 calc R . . . .
C43 C -0.19135(13) 0.47413(9) 0.90940(8) 0.0260(3) Uani 1 1 d . . . . .
H43 H -0.2661 0.4537 0.9430 0.031 Uiso 1 1 calc R . . . .
C44 C -0.19254(12) 0.51694(9) 0.84119(8) 0.0254(3) Uani 1 1 d . . . . .
H44 H -0.2684 0.5259 0.8280 0.031 Uiso 1 1 calc R . . . .
C45 C -0.08313(12) 0.54676(8) 0.79202(7) 0.0204(3) Uani 1 1 d . . . . .
H45 H -0.0852 0.5753 0.7451 0.025 Uiso 1 1 calc R . . . .
C46 C 0.15601(11) 0.78005(8) 0.62658(7) 0.0197(3) Uani 1 1 d . . . . .
C47 C 0.08284(12) 0.76208(9) 0.57922(8) 0.0238(3) Uani 1 1 d . . . . .
H47 H 0.0460 0.7079 0.5843 0.029 Uiso 1 1 calc R . . . .
C48 C 0.06312(13) 0.82225(10) 0.52483(8) 0.0286(3) Uani 1 1 d . . . . .
H48 H 0.0140 0.8087 0.4926 0.034 Uiso 1 1 calc R . . . .
C49 C 0.11480(13) 0.90207(9) 0.51741(8) 0.0278(3) Uani 1 1 d . . . . .
H49 H 0.1009 0.9433 0.4803 0.033 Uiso 1 1 calc R . . . .
C50 C 0.18659(13) 0.92165(9) 0.56409(8) 0.0253(3) Uani 1 1 d . . . . .
H50 H 0.2219 0.9765 0.5593 0.030 Uiso 1 1 calc R . . . .
C51 C 0.20707(12) 0.86104(9) 0.61803(8) 0.0232(3) Uani 1 1 d . . . . .
H51 H 0.2568 0.8749 0.6498 0.028 Uiso 1 1 calc R . . . .
C52 C 0.39831(12) 0.69850(8) 0.81482(8) 0.0210(3) Uani 1 1 d . . . . .
C53 C 0.48290(13) 0.75930(9) 0.77943(8) 0.0258(3) Uani 1 1 d . . . . .
H53 H 0.4741 0.7894 0.7346 0.031 Uiso 1 1 calc R . . . .
C54 C 0.57934(14) 0.77645(10) 0.80865(9) 0.0324(3) Uani 1 1 d . . . . .
H54 H 0.6366 0.8174 0.7835 0.039 Uiso 1 1 calc R . . . .
C55 C 0.59192(14) 0.73390(10) 0.87443(10) 0.0337(3) Uani 1 1 d . . . . .
H55 H 0.6582 0.7453 0.8943 0.040 Uiso 1 1 calc R . . . .
C56 C 0.50821(15) 0.67475(10) 0.91140(9) 0.0332(3) Uani 1 1 d . . . . .
H56 H 0.5162 0.6461 0.9571 0.040 Uiso 1 1 calc R . . . .
C57 C 0.41271(13) 0.65739(9) 0.88171(8) 0.0271(3) Uani 1 1 d . . . . .
H57 H 0.3557 0.6166 0.9074 0.033 Uiso 1 1 calc R . . . .
B4 B 0.15670(13) 0.56986(9) 0.75276(8) 0.0183(3) Uani 1 1 d . . . . .
B5 B 0.18607(13) 0.71047(10) 0.68466(8) 0.0195(3) Uani 1 1 d . . . . .
B6 B 0.29609(13) 0.67404(10) 0.77716(8) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.22821(12) -0.04798(9) 0.83916(8) 0.0312(3) Uani 1 1 d . . . . .
H2A H 0.2206(19) -0.0487(14) 0.7914(13) 0.058(6) Uiso 1 1 d . . . . .
H2B H 0.2744(19) -0.1031(14) 0.8449(12) 0.058(6) Uiso 1 1 d . . . . .
C26 C 0.10327(13) -0.04380(10) 0.89817(10) 0.0326(3) Uani 1 1 d . . . . .
H26A H 0.0476 0.0032 0.8837 0.039 Uiso 1 1 calc R . . . .
H26B H 0.1113 -0.0261 0.9493 0.039 Uiso 1 1 calc R . . . .
C27 C 0.04014(12) -0.12830(9) 0.90855(9) 0.0275(3) Uani 1 1 d . . . . .
C28 C 0.01575(13) -0.17149(10) 0.97905(9) 0.0315(3) Uani 1 1 d . . . . .
H28 H 0.0411 -0.1486 1.0203 0.038 Uiso 1 1 calc R . . . .
C29 C -0.04533(14) -0.24785(10) 0.99016(10) 0.0364(4) Uani 1 1 d . . . . .
H29 H -0.0616 -0.2768 1.0388 0.044 Uiso 1 1 calc R . . . .
C30 C -0.08246(14) -0.28174(10) 0.93055(10) 0.0377(4) Uani 1 1 d . . . . .
H30 H -0.1255 -0.3334 0.9384 0.045 Uiso 1 1 calc R . . . .
C31 C -0.05660(13) -0.24017(10) 0.85945(10) 0.0341(3) Uani 1 1 d . . . . .
H31 H -0.0807 -0.2639 0.8180 0.041 Uiso 1 1 calc R . . . .
C32 C 0.00438(13) -0.16404(9) 0.84846(9) 0.0302(3) Uani 1 1 d . . . . .
H32 H 0.0220 -0.1360 0.7994 0.036 Uiso 1 1 calc R . . . .
N4 N 0.06124(13) 0.42735(10) 0.61848(7) 0.0316(3) Uani 1 1 d . . . . .
H4A H 0.0202(18) 0.3920(13) 0.6556(12) 0.051(5) Uiso 1 1 d . . . . .
H4B H 0.0007(19) 0.4723(13) 0.6133(11) 0.052(6) Uiso 1 1 d . . . . .
C58 C 0.10996(15) 0.37504(10) 0.54524(9) 0.0326(3) Uani 1 1 d . . . . .
H58A H 0.0397 0.3485 0.5346 0.039 Uiso 1 1 calc R . . . .
H58B H 0.1709 0.3262 0.5515 0.039 Uiso 1 1 calc R . . . .
C59 C 0.17360(13) 0.42860(9) 0.47589(8) 0.0248(3) Uani 1 1 d . . . . .
C60 C 0.22700(15) 0.38679(10) 0.40270(9) 0.0335(3) Uani 1 1 d . . . . .
H60 H 0.2218 0.3253 0.3971 0.040 Uiso 1 1 calc R . . . .
C61 C 0.28751(15) 0.43329(12) 0.33800(9) 0.0370(4) Uani 1 1 d . . . . .
H61 H 0.3242 0.4036 0.2885 0.044 Uiso 1 1 calc R . . . .
C62 C 0.29484(14) 0.52295(11) 0.34502(9) 0.0354(4) Uani 1 1 d . . . . .
H62 H 0.3357 0.5551 0.3005 0.042 Uiso 1 1 calc R . . . .
C63 C 0.24224(14) 0.56529(10) 0.41737(9) 0.0321(3) Uani 1 1 d . . . . .
H63 H 0.2473 0.6268 0.4226 0.039 Uiso 1 1 calc R . . . .
C64 C 0.18201(13) 0.51854(9) 0.48249(8) 0.0261(3) Uani 1 1 d . . . . .
H64 H 0.1463 0.5483 0.5320 0.031 Uiso 1 1 calc R . . . .
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
O1 0.0167(4) 0.0204(5) 0.0236(5) 0.0016(4) -0.0069(4) -0.0007(3)
O2 0.0210(5) 0.0241(5) 0.0248(5) -0.0016(4) -0.0096(4) 0.0005(4)
O3 0.0181(4) 0.0205(5) 0.0234(5) 0.0008(4) -0.0087(4) 0.0008(3)
N1 0.0153(5) 0.0194(6) 0.0242(6) 0.0038(5) -0.0078(4) -0.0030(4)
C1 0.0191(6) 0.0291(7) 0.0303(7) 0.0116(6) -0.0117(5) -0.0060(5)
C2 0.0148(6) 0.0239(7) 0.0267(7) 0.0083(5) -0.0100(5) -0.0025(5)
C3 0.0256(7) 0.0278(7) 0.0305(7) 0.0026(6) -0.0141(6) 0.0022(5)
C4 0.0353(8) 0.0210(7) 0.0520(10) 0.0101(7) -0.0254(7) -0.0047(6)
C5 0.0256(7) 0.0366(9) 0.0451(9) 0.0236(7) -0.0153(7) -0.0095(6)
C6 0.0250(7) 0.0439(9) 0.0298(8) 0.0113(7) -0.0038(6) -0.0001(6)
C7 0.0246(7) 0.0244(7) 0.0325(7) 0.0036(6) -0.0089(6) 0.0005(5)
C8 0.0182(6) 0.0199(6) 0.0160(6) 0.0050(5) -0.0050(5) -0.0034(5)
C9 0.0184(6) 0.0210(7) 0.0256(7) 0.0021(5) -0.0065(5) 0.0001(5)
C10 0.0171(6) 0.0298(7) 0.0318(7) 0.0016(6) -0.0071(5) -0.0062(5)
C11 0.0237(7) 0.0238(7) 0.0334(8) -0.0013(6) -0.0073(6) -0.0083(5)
C12 0.0214(7) 0.0206(7) 0.0377(8) -0.0028(6) -0.0053(6) -0.0005(5)
C13 0.0153(6) 0.0240(7) 0.0293(7) 0.0022(5) -0.0058(5) -0.0033(5)
C14 0.0214(6) 0.0178(6) 0.0253(7) 0.0035(5) -0.0041(5) -0.0027(5)
C15 0.0259(7) 0.0302(8) 0.0310(7) 0.0002(6) -0.0085(6) 0.0033(6)
C16 0.0253(7) 0.0347(9) 0.0432(9) 0.0028(7) -0.0075(7) 0.0072(6)
C17 0.0318(8) 0.0221(7) 0.0432(9) -0.0034(6) 0.0007(7) 0.0040(6)
C18 0.0363(8) 0.0277(8) 0.0381(8) -0.0087(7) -0.0039(7) -0.0068(6)
C19 0.0239(7) 0.0261(7) 0.0345(8) -0.0016(6) -0.0070(6) -0.0045(5)
C20 0.0206(6) 0.0263(7) 0.0177(6) 0.0049(5) -0.0065(5) -0.0031(5)
C21 0.0298(8) 0.0436(9) 0.0252(7) -0.0061(6) -0.0100(6) -0.0028(6)
C22 0.0338(8) 0.0717(13) 0.0279(8) -0.0005(8) -0.0179(7) -0.0147(8)
C23 0.0210(7) 0.0722(12) 0.0314(8) 0.0211(8) -0.0116(6) -0.0035(7)
C24 0.0208(7) 0.0398(9) 0.0375(8) 0.0185(7) -0.0031(6) 0.0025(6)
C25 0.0216(6) 0.0254(7) 0.0280(7) 0.0080(6) -0.0054(5) -0.0029(5)
B1 0.0161(6) 0.0187(7) 0.0210(7) 0.0038(5) -0.0075(5) -0.0019(5)
B2 0.0206(7) 0.0174(7) 0.0232(7) 0.0051(6) -0.0058(6) -0.0037(5)
B3 0.0200(7) 0.0181(7) 0.0225(7) 0.0048(6) -0.0081(6) -0.0024(5)
O4 0.0193(4) 0.0199(5) 0.0215(4) 0.0027(4) -0.0079(4) -0.0035(3)
O5 0.0239(5) 0.0219(5) 0.0277(5) 0.0048(4) -0.0117(4) -0.0073(4)
O6 0.0193(4) 0.0193(5) 0.0228(5) 0.0013(4) -0.0085(4) -0.0033(3)
N3 0.0173(5) 0.0183(6) 0.0206(5) 0.0012(4) -0.0022(4) -0.0032(4)
C33 0.0192(6) 0.0220(7) 0.0278(7) 0.0009(5) 0.0024(5) -0.0043(5)
C34 0.0149(6) 0.0199(6) 0.0245(6) 0.0009(5) -0.0005(5) -0.0048(5)
C35 0.0206(6) 0.0284(7) 0.0238(7) 0.0031(5) -0.0044(5) -0.0047(5)
C36 0.0295(7) 0.0351(8) 0.0262(7) -0.0077(6) -0.0017(6) -0.0050(6)
C37 0.0245(7) 0.0218(7) 0.0399(8) -0.0039(6) 0.0003(6) -0.0005(5)
C38 0.0217(7) 0.0248(7) 0.0346(8) 0.0080(6) -0.0037(6) -0.0032(5)
C39 0.0222(6) 0.0271(7) 0.0217(7) 0.0032(5) -0.0012(5) -0.0055(5)
C40 0.0180(6) 0.0138(6) 0.0197(6) -0.0042(5) -0.0036(5) -0.0002(4)
C41 0.0195(6) 0.0205(6) 0.0237(6) -0.0008(5) -0.0075(5) 0.0008(5)
C42 0.0295(7) 0.0245(7) 0.0189(6) 0.0023(5) -0.0051(5) -0.0043(5)
C43 0.0234(7) 0.0302(8) 0.0225(7) -0.0013(6) -0.0018(5) -0.0107(5)
C44 0.0202(6) 0.0323(8) 0.0258(7) -0.0018(6) -0.0087(5) -0.0069(5)
C45 0.0213(6) 0.0218(7) 0.0194(6) -0.0001(5) -0.0074(5) -0.0044(5)
C46 0.0172(6) 0.0199(6) 0.0191(6) -0.0004(5) -0.0021(5) 0.0003(5)
C47 0.0218(6) 0.0209(7) 0.0284(7) 0.0021(5) -0.0075(5) -0.0022(5)
C48 0.0281(7) 0.0308(8) 0.0307(7) 0.0028(6) -0.0153(6) -0.0011(6)
C49 0.0299(7) 0.0250(7) 0.0255(7) 0.0050(6) -0.0067(6) 0.0054(6)
C50 0.0296(7) 0.0175(6) 0.0251(7) 0.0001(5) -0.0036(6) -0.0005(5)
C51 0.0248(7) 0.0222(7) 0.0218(6) -0.0011(5) -0.0061(5) -0.0024(5)
C52 0.0196(6) 0.0173(6) 0.0260(7) -0.0032(5) -0.0073(5) -0.0004(5)
C53 0.0262(7) 0.0236(7) 0.0288(7) 0.0011(6) -0.0094(6) -0.0048(5)
C54 0.0253(7) 0.0301(8) 0.0442(9) 0.0006(7) -0.0117(6) -0.0107(6)
C55 0.0302(8) 0.0297(8) 0.0498(9) -0.0067(7) -0.0247(7) -0.0035(6)
C56 0.0419(9) 0.0275(8) 0.0391(8) 0.0026(6) -0.0253(7) -0.0045(6)
C57 0.0316(7) 0.0214(7) 0.0323(7) 0.0030(6) -0.0142(6) -0.0077(5)
B4 0.0176(7) 0.0174(7) 0.0198(7) -0.0004(5) -0.0055(5) -0.0020(5)
B5 0.0163(7) 0.0207(7) 0.0191(7) -0.0007(6) -0.0023(5) -0.0006(5)
B6 0.0179(7) 0.0189(7) 0.0209(7) -0.0019(6) -0.0043(6) -0.0004(5)
N2 0.0324(7) 0.0315(7) 0.0298(7) 0.0027(6) -0.0068(5) -0.0131(5)
C26 0.0251(7) 0.0232(7) 0.0481(9) -0.0037(6) -0.0086(7) -0.0050(6)
C27 0.0163(6) 0.0193(7) 0.0423(8) -0.0061(6) -0.0028(6) -0.0006(5)
C28 0.0227(7) 0.0284(8) 0.0401(8) -0.0058(6) -0.0059(6) 0.0009(6)
C29 0.0295(8) 0.0259(8) 0.0437(9) 0.0021(7) 0.0019(7) 0.0015(6)
C30 0.0259(7) 0.0193(7) 0.0568(10) -0.0086(7) 0.0042(7) -0.0045(6)
C31 0.0249(7) 0.0261(8) 0.0458(9) -0.0144(7) -0.0027(6) -0.0027(6)
C32 0.0238(7) 0.0240(7) 0.0372(8) -0.0051(6) -0.0016(6) -0.0007(5)
N4 0.0346(7) 0.0359(8) 0.0275(7) 0.0075(6) -0.0104(5) -0.0162(6)
C58 0.0436(9) 0.0259(8) 0.0339(8) 0.0035(6) -0.0177(7) -0.0121(6)
C59 0.0246(7) 0.0253(7) 0.0284(7) 0.0012(6) -0.0142(6) -0.0025(5)
C60 0.0401(8) 0.0307(8) 0.0341(8) -0.0043(6) -0.0191(7) 0.0013(6)
C61 0.0335(8) 0.0516(10) 0.0259(7) -0.0046(7) -0.0116(6) 0.0040(7)
C62 0.0271(7) 0.0518(10) 0.0290(8) 0.0110(7) -0.0097(6) -0.0092(7)
C63 0.0295(8) 0.0320(8) 0.0374(8) 0.0065(6) -0.0124(6) -0.0094(6)
C64 0.0242(7) 0.0266(7) 0.0278(7) 0.0003(6) -0.0084(6) -0.0038(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
O1 B1 1.4580(16) . ?
O1 B2 1.3449(17) . ?
O2 B2 1.3947(17) . ?
O2 B3 1.3871(17) . ?
O3 B1 1.4619(16) . ?
O3 B3 1.3433(17) . ?
N1 C1 1.4908(16) . ?
N1 B1 1.6335(17) . ?
C1 C2 1.5049(18) . ?
C2 C3 1.3883(19) . ?
C2 C7 1.3857(19) . ?
C3 C4 1.386(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.377(2) . ?
C6 C7 1.386(2) . ?
C8 C9 1.3938(17) . ?
C8 C13 1.3979(18) . ?
C8 B1 1.5997(19) . ?
C9 C10 1.3860(19) . ?
C10 C11 1.383(2) . ?
C11 C12 1.3865(19) . ?
C12 C13 1.3854(19) . ?
C14 C15 1.3976(19) . ?
C14 C19 1.394(2) . ?
C14 B2 1.5668(19) . ?
C15 C16 1.388(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.379(2) . ?
C18 C19 1.389(2) . ?
C20 C21 1.392(2) . ?
C20 C25 1.3971(19) . ?
C20 B3 1.5725(18) . ?
C21 C22 1.394(2) . ?
C22 C23 1.378(3) . ?
C23 C24 1.374(2) . ?
C24 C25 1.3869(19) . ?
O4 B4 1.4627(16) . ?
O4 B5 1.3433(17) . ?
O5 B5 1.3867(17) . ?
O5 B6 1.3817(17) . ?
O6 B4 1.4700(16) . ?
O6 B6 1.3472(17) . ?
N3 C33 1.4944(16) . ?
N3 B4 1.6303(17) . ?
C33 C34 1.5055(18) . ?
C34 C35 1.3878(19) . ?
C34 C39 1.3930(19) . ?
C35 C36 1.389(2) . ?
C36 C37 1.384(2) . ?
C37 C38 1.380(2) . ?
C38 C39 1.3800(19) . ?
C40 C41 1.3975(17) . ?
C40 C45 1.3970(17) . ?
C40 B4 1.6102(18) . ?
C41 C42 1.3897(18) . ?
C42 C43 1.3832(19) . ?
C43 C44 1.3863(19) . ?
C44 C45 1.3901(18) . ?
C46 C47 1.3965(18) . ?
C46 C51 1.3975(18) . ?
C46 B5 1.5669(19) . ?
C47 C48 1.3868(19) . ?
C48 C49 1.385(2) . ?
C49 C50 1.381(2) . ?
C50 C51 1.3876(19) . ?
C52 C53 1.3990(18) . ?
C52 C57 1.3961(19) . ?
C52 B6 1.5750(19) . ?
C53 C54 1.388(2) . ?
C54 C55 1.381(2) . ?
C55 C56 1.382(2) . ?
C56 C57 1.384(2) . ?
N2 C26 1.4702(19) . ?
C26 C27 1.5117(19) . ?
C27 C28 1.385(2) . ?
C27 C32 1.391(2) . ?
C28 C29 1.389(2) . ?
C29 C30 1.380(2) . ?
C30 C31 1.382(2) . ?
C31 C32 1.386(2) . ?
N4 C58 1.462(2) . ?
C58 C59 1.509(2) . ?
C59 C60 1.391(2) . ?
C59 C64 1.3883(19) . ?
C60 C61 1.382(2) . ?
C61 C62 1.383(2) . ?
C62 C63 1.381(2) . ?
C63 C64 1.388(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
B2 O1 B1 121.96(10) . . ?
B3 O2 B2 118.70(11) . . ?
B3 O3 B1 121.97(10) . . ?
C1 N1 B1 117.23(10) . . ?
N1 C1 C2 110.17(10) . . ?
C3 C2 C1 120.80(12) . . ?
C7 C2 C1 120.39(12) . . ?
C7 C2 C3 118.70(12) . . ?
C4 C3 C2 120.49(14) . . ?
C5 C4 C3 120.17(14) . . ?
C6 C5 C4 119.78(14) . . ?
C5 C6 C7 120.07(14) . . ?
C2 C7 C6 120.75(14) . . ?
C9 C8 C13 116.74(12) . . ?
C9 C8 B1 122.35(11) . . ?
C13 C8 B1 120.87(11) . . ?
C10 C9 C8 121.87(12) . . ?
C11 C10 C9 120.14(12) . . ?
C10 C11 C12 119.40(13) . . ?
C13 C12 C11 119.86(13) . . ?
C12 C13 C8 121.99(12) . . ?
C15 C14 B2 119.88(12) . . ?
C19 C14 C15 117.49(13) . . ?
C19 C14 B2 122.63(12) . . ?
C16 C15 C14 121.29(14) . . ?
C17 C16 C15 119.84(14) . . ?
C18 C17 C16 120.12(14) . . ?
C17 C18 C19 119.75(14) . . ?
C18 C19 C14 121.52(14) . . ?
C21 C20 C25 117.64(12) . . ?
C21 C20 B3 122.35(12) . . ?
C25 C20 B3 120.00(12) . . ?
C20 C21 C22 120.96(15) . . ?
C23 C22 C21 120.14(15) . . ?
C24 C23 C22 119.76(14) . . ?
C23 C24 C25 120.32(15) . . ?
C24 C25 C20 121.12(14) . . ?
O1 B1 O3 113.21(10) . . ?
O1 B1 N1 103.61(10) . . ?
O1 B1 C8 113.40(10) . . ?
O3 B1 N1 102.93(9) . . ?
O3 B1 C8 111.70(10) . . ?
C8 B1 N1 111.17(10) . . ?
O1 B2 O2 121.43(12) . . ?
O1 B2 C14 118.87(12) . . ?
O2 B2 C14 119.70(12) . . ?
O2 B3 C20 120.24(12) . . ?
O3 B3 O2 121.69(12) . . ?
O3 B3 C20 118.06(12) . . ?
B5 O4 B4 122.20(10) . . ?
B6 O5 B5 119.37(11) . . ?
B6 O6 B4 122.01(10) . . ?
C33 N3 B4 117.14(10) . . ?
N3 C33 C34 111.57(10) . . ?
C35 C34 C33 121.25(12) . . ?
C35 C34 C39 119.05(12) . . ?
C39 C34 C33 119.70(12) . . ?
C34 C35 C36 120.19(13) . . ?
C37 C36 C35 120.11(13) . . ?
C38 C37 C36 119.96(13) . . ?
C39 C38 C37 120.06(13) . . ?
C38 C39 C34 120.63(13) . . ?
C41 C40 B4 121.56(11) . . ?
C45 C40 C41 116.87(11) . . ?
C45 C40 B4 121.56(11) . . ?
C42 C41 C40 122.03(12) . . ?
C43 C42 C41 119.83(12) . . ?
C42 C43 C44 119.48(12) . . ?
C43 C44 C45 120.22(12) . . ?
C44 C45 C40 121.55(12) . . ?
C47 C46 C51 117.80(12) . . ?
C47 C46 B5 121.61(12) . . ?
C51 C46 B5 120.53(12) . . ?
C48 C47 C46 120.95(13) . . ?
C49 C48 C47 120.17(13) . . ?
C50 C49 C48 119.92(13) . . ?
C49 C50 C51 119.82(13) . . ?
C50 C51 C46 121.34(13) . . ?
C53 C52 B6 120.62(12) . . ?
C57 C52 C53 117.51(12) . . ?
C57 C52 B6 121.78(12) . . ?
C54 C53 C52 121.20(13) . . ?
C55 C54 C53 119.87(14) . . ?
C54 C55 C56 120.12(13) . . ?
C55 C56 C57 119.79(14) . . ?
C56 C57 C52 121.49(13) . . ?
O4 B4 O6 113.13(10) . . ?
O4 B4 N3 105.36(10) . . ?
O4 B4 C40 113.11(10) . . ?
O6 B4 N3 105.90(10) . . ?
O6 B4 C40 113.15(10) . . ?
C40 B4 N3 105.26(10) . . ?
O4 B5 O5 121.51(12) . . ?
O4 B5 C46 121.53(12) . . ?
O5 B5 C46 116.94(11) . . ?
O5 B6 C52 116.92(11) . . ?
O6 B6 O5 121.41(12) . . ?
O6 B6 C52 121.60(12) . . ?
N2 C26 C27 115.79(12) . . ?
C28 C27 C26 120.21(14) . . ?
C28 C27 C32 118.54(13) . . ?
C32 C27 C26 121.25(14) . . ?
C27 C28 C29 120.83(15) . . ?
C30 C29 C28 120.07(15) . . ?
C29 C30 C31 119.64(14) . . ?
C30 C31 C32 120.20(15) . . ?
C31 C32 C27 120.70(15) . . ?
N4 C58 C59 113.08(12) . . ?
C60 C59 C58 119.27(13) . . ?
C64 C59 C58 122.33(13) . . ?
C64 C59 C60 118.39(13) . . ?
C61 C60 C59 121.01(14) . . ?
C60 C61 C62 120.21(14) . . ?
C63 C62 C61 119.38(14) . . ?
C62 C63 C64 120.46(14) . . ?
C63 C64 C59 120.55(13) . . ?
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
N1 H1A N2 0.938(16) 2.058(17) 2.9956(17) 177.6(13) .
N3 H3B N4 0.936(18) 2.020(19) 2.9520(17) 173.7(16) .
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
15srv282.res created by SHELXL-2014/7
TITL 15srv282 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 11.2396 15.2054 17.9361 89.7333 72.0196 84.3291
ZERR 4 0.0004 0.0006 0.0007 0.0016 0.0015 0.0017
LATT 1
SFAC C H B N O
UNIT 128 132 12 8 12
L.S. 7
PLAN 10
TEMP -153.15
HTAB N3 N4
HTAB N1 N2
BOND
fmap 2
acta
OMIT 1 0 0
REM
REM
REM
WGHT 0.043000 0.946000
FVAR 0.15305
O1 5 0.449507 0.115401 0.769786 11.00000 0.01668 0.02037 =
0.02362 0.00158 -0.00689 -0.00070
O2 5 0.309470 0.090052 0.697205 11.00000 0.02104 0.02409 =
0.02478 -0.00162 -0.00961 0.00051
O3 5 0.239832 0.194923 0.804090 11.00000 0.01809 0.02051 =
0.02344 0.00082 -0.00874 0.00080
N1 4 0.305863 0.111382 0.902393 11.00000 0.01529 0.01941 =
0.02418 0.00382 -0.00776 -0.00296
H1A 2 0.279614 0.062533 0.882331 11.00000 0.02685
H1B 2 0.235936 0.139934 0.937522 11.00000 0.02495
C1 1 0.399104 0.080475 0.943060 11.00000 0.01905 0.02911 =
0.03034 0.01158 -0.01175 -0.00595
AFIX 23
H1C 2 0.419439 0.131403 0.969399 11.00000 -1.20000
H1D 2 0.477626 0.053994 0.904158 11.00000 -1.20000
AFIX 0
C2 1 0.346649 0.013032 1.002739 11.00000 0.01482 0.02390 =
0.02670 0.00827 -0.01004 -0.00252
C3 1 0.360332 -0.075990 0.981602 11.00000 0.02557 0.02777 =
0.03054 0.00264 -0.01411 0.00220
AFIX 43
H3 2 0.409952 -0.095462 0.930150 11.00000 -1.20000
AFIX 0
C4 1 0.302114 -0.136687 1.035029 11.00000 0.03533 0.02098 =
0.05198 0.01012 -0.02544 -0.00467
AFIX 43
H4 2 0.311140 -0.197369 1.019855 11.00000 -1.20000
AFIX 0
C5 1 0.231067 -0.109178 1.110217 11.00000 0.02558 0.03662 =
0.04513 0.02362 -0.01531 -0.00946
AFIX 43
H5 2 0.189994 -0.150648 1.146501 11.00000 -1.20000
AFIX 0
C6 1 0.219930 -0.021408 1.132450 11.00000 0.02502 0.04390 =
0.02984 0.01129 -0.00376 -0.00007
AFIX 43
H6 2 0.172880 -0.002541 1.184546 11.00000 -1.20000
AFIX 0
C7 1 0.277303 0.039427 1.078892 11.00000 0.02459 0.02443 =
0.03251 0.00359 -0.00886 0.00047
AFIX 43
H7 2 0.268989 0.099899 1.094571 11.00000 -1.20000
AFIX 0
C8 1 0.405210 0.260526 0.849576 11.00000 0.01824 0.01994 =
0.01604 0.00496 -0.00496 -0.00342
C9 1 0.530552 0.262998 0.845838 11.00000 0.01837 0.02103 =
0.02556 0.00205 -0.00653 0.00011
AFIX 43
H9 2 0.587057 0.210834 0.830589 11.00000 -1.20000
AFIX 0
C10 1 0.575089 0.339400 0.863736 11.00000 0.01714 0.02977 =
0.03179 0.00164 -0.00714 -0.00620
AFIX 43
H10 2 0.660806 0.338842 0.861293 11.00000 -1.20000
AFIX 0
C11 1 0.494976 0.416477 0.885154 11.00000 0.02373 0.02385 =
0.03343 -0.00135 -0.00728 -0.00828
AFIX 43
H11 2 0.525412 0.469046 0.897078 11.00000 -1.20000
AFIX 0
C12 1 0.369858 0.416300 0.889057 11.00000 0.02140 0.02062 =
0.03768 -0.00284 -0.00528 -0.00048
AFIX 43
H12 2 0.314174 0.468960 0.903395 11.00000 -1.20000
AFIX 0
C13 1 0.326220 0.339169 0.872002 11.00000 0.01530 0.02399 =
0.02926 0.00217 -0.00575 -0.00331
AFIX 43
H13 2 0.240004 0.339740 0.875660 11.00000 -1.20000
AFIX 0
C14 1 0.528910 0.004741 0.657671 11.00000 0.02141 0.01777 =
0.02534 0.00355 -0.00409 -0.00273
C15 1 0.641950 -0.015824 0.674207 11.00000 0.02595 0.03018 =
0.03103 0.00018 -0.00850 0.00328
AFIX 43
H15 2 0.654900 0.012472 0.717769 11.00000 -1.20000
AFIX 0
C16 1 0.735653 -0.076773 0.628235 11.00000 0.02527 0.03471 =
0.04318 0.00276 -0.00752 0.00717
AFIX 43
H16 2 0.811868 -0.089908 0.640401 11.00000 -1.20000
AFIX 0
C17 1 0.717800 -0.118349 0.564652 11.00000 0.03180 0.02207 =
0.04317 -0.00341 0.00073 0.00397
AFIX 43
H17 2 0.781762 -0.160198 0.533203 11.00000 -1.20000
AFIX 0
C18 1 0.607314 -0.099155 0.546835 11.00000 0.03633 0.02769 =
0.03812 -0.00870 -0.00386 -0.00681
AFIX 43
H18 2 0.595151 -0.127562 0.503070 11.00000 -1.20000
AFIX 0
C19 1 0.513898 -0.038140 0.593118 11.00000 0.02389 0.02605 =
0.03446 -0.00158 -0.00705 -0.00450
AFIX 43
H19 2 0.438018 -0.025329 0.580497 11.00000 -1.20000
AFIX 0
C20 1 0.091260 0.176750 0.727474 11.00000 0.02057 0.02629 =
0.01771 0.00491 -0.00645 -0.00312
C21 1 0.043246 0.119558 0.686315 11.00000 0.02977 0.04361 =
0.02521 -0.00613 -0.00999 -0.00279
AFIX 43
H21 2 0.090230 0.064764 0.666053 11.00000 -1.20000
AFIX 0
C22 1 -0.072809 0.141511 0.674385 11.00000 0.03379 0.07166 =
0.02792 -0.00049 -0.01786 -0.01474
AFIX 43
H22 2 -0.105449 0.100975 0.647556 11.00000 -1.20000
AFIX 0
C23 1 -0.140251 0.221879 0.701429 11.00000 0.02102 0.07216 =
0.03145 0.02108 -0.01159 -0.00351
AFIX 43
H23 2 -0.217953 0.237657 0.691732 11.00000 -1.20000
AFIX 0
C24 1 -0.094730 0.279099 0.742459 11.00000 0.02080 0.03982 =
0.03754 0.01849 -0.00309 0.00254
AFIX 43
H24 2 -0.141353 0.334398 0.761369 11.00000 -1.20000
AFIX 0
C25 1 0.018968 0.256530 0.756411 11.00000 0.02156 0.02540 =
0.02798 0.00803 -0.00539 -0.00290
AFIX 43
H25 2 0.048190 0.295991 0.786150 11.00000 -1.20000
AFIX 0
B1 3 0.353539 0.173586 0.826601 11.00000 0.01611 0.01871 =
0.02104 0.00379 -0.00746 -0.00193
B2 3 0.424997 0.073601 0.711074 11.00000 0.02057 0.01735 =
0.02324 0.00515 -0.00578 -0.00369
B3 3 0.220300 0.153243 0.743682 11.00000 0.01998 0.01805 =
0.02248 0.00484 -0.00808 -0.00236
O4 5 0.133588 0.633904 0.696426 11.00000 0.01934 0.01990 =
0.02149 0.00273 -0.00789 -0.00350
O5 5 0.271332 0.730734 0.722129 11.00000 0.02388 0.02186 =
0.02774 0.00482 -0.01171 -0.00727
O6 5 0.239493 0.599234 0.795029 11.00000 0.01927 0.01930 =
0.02275 0.00130 -0.00854 -0.00332
N3 4 0.233656 0.483151 0.700208 11.00000 0.01731 0.01833 =
0.02055 0.00116 -0.00221 -0.00322
H3A 2 0.243084 0.438902 0.732957 11.00000 0.02922
H3B 2 0.183949 0.462477 0.672059 11.00000 0.04159
C33 1 0.359360 0.494625 0.642914 11.00000 0.01918 0.02196 =
0.02780 0.00093 0.00241 -0.00426
AFIX 23
H33A 2 0.410047 0.524222 0.669722 11.00000 -1.20000
H33B 2 0.348017 0.533060 0.600410 11.00000 -1.20000
AFIX 0
C34 1 0.428790 0.407263 0.608015 11.00000 0.01488 0.01985 =
0.02446 0.00086 -0.00048 -0.00482
C35 1 0.453772 0.386175 0.529102 11.00000 0.02063 0.02841 =
0.02385 0.00314 -0.00437 -0.00471
AFIX 43
H35 2 0.425814 0.426930 0.496246 11.00000 -1.20000
AFIX 0
C36 1 0.519541 0.305645 0.498020 11.00000 0.02953 0.03513 =
0.02622 -0.00768 -0.00174 -0.00497
AFIX 43
H36 2 0.536811 0.291562 0.443922 11.00000 -1.20000
AFIX 0
C37 1 0.559941 0.245907 0.545731 11.00000 0.02445 0.02177 =
0.03988 -0.00385 0.00027 -0.00050
AFIX 43
H37 2 0.605314 0.190994 0.524338 11.00000 -1.20000
AFIX 0
C38 1 0.534278 0.266148 0.624425 11.00000 0.02171 0.02477 =
0.03462 0.00803 -0.00372 -0.00322
AFIX 43
H38 2 0.560989 0.224798 0.657334 11.00000 -1.20000
AFIX 0
C39 1 0.469857 0.346393 0.655341 11.00000 0.02219 0.02713 =
0.02166 0.00321 -0.00119 -0.00553
AFIX 43
H39 2 0.453360 0.360253 0.709412 11.00000 -1.20000
AFIX 0
C40 1 0.029796 0.535786 0.809935 11.00000 0.01797 0.01383 =
0.01973 -0.00418 -0.00361 -0.00023
C41 1 0.028089 0.492163 0.878951 11.00000 0.01945 0.02055 =
0.02369 -0.00077 -0.00749 0.00084
AFIX 43
H41 2 0.103503 0.483219 0.892632 11.00000 -1.20000
AFIX 0
C42 1 -0.080525 0.461461 0.928190 11.00000 0.02953 0.02452 =
0.01891 0.00234 -0.00507 -0.00432
AFIX 43
H42 2 -0.078662 0.431848 0.974633 11.00000 -1.20000
AFIX 0
C43 1 -0.191352 0.474132 0.909405 11.00000 0.02344 0.03018 =
0.02247 -0.00130 -0.00179 -0.01068
AFIX 43
H43 2 -0.266064 0.453658 0.942986 11.00000 -1.20000
AFIX 0
C44 1 -0.192544 0.516942 0.841188 11.00000 0.02019 0.03234 =
0.02575 -0.00179 -0.00869 -0.00688
AFIX 43
H44 2 -0.268389 0.525932 0.828000 11.00000 -1.20000
AFIX 0
C45 1 -0.083133 0.546757 0.792017 11.00000 0.02132 0.02181 =
0.01938 -0.00012 -0.00744 -0.00440
AFIX 43
H45 2 -0.085206 0.575264 0.745126 11.00000 -1.20000
AFIX 0
C46 1 0.156006 0.780055 0.626579 11.00000 0.01721 0.01985 =
0.01906 -0.00037 -0.00214 0.00029
C47 1 0.082839 0.762082 0.579221 11.00000 0.02181 0.02091 =
0.02838 0.00206 -0.00746 -0.00219
AFIX 43
H47 2 0.046047 0.707857 0.584342 11.00000 -1.20000
AFIX 0
C48 1 0.063117 0.822253 0.524825 11.00000 0.02807 0.03084 =
0.03073 0.00284 -0.01530 -0.00113
AFIX 43
H48 2 0.014024 0.808689 0.492566 11.00000 -1.20000
AFIX 0
C49 1 0.114805 0.902069 0.517408 11.00000 0.02995 0.02497 =
0.02553 0.00499 -0.00667 0.00544
AFIX 43
H49 2 0.100897 0.943298 0.480257 11.00000 -1.20000
AFIX 0
C50 1 0.186594 0.921648 0.564088 11.00000 0.02959 0.01750 =
0.02508 0.00006 -0.00357 -0.00048
AFIX 43
H50 2 0.221857 0.976454 0.559279 11.00000 -1.20000
AFIX 0
C51 1 0.207070 0.861044 0.618030 11.00000 0.02484 0.02220 =
0.02182 -0.00115 -0.00611 -0.00237
AFIX 43
H51 2 0.256812 0.874890 0.649794 11.00000 -1.20000
AFIX 0
C52 1 0.398313 0.698497 0.814823 11.00000 0.01960 0.01733 =
0.02604 -0.00325 -0.00731 -0.00038
C53 1 0.482896 0.759301 0.779435 11.00000 0.02623 0.02359 =
0.02881 0.00108 -0.00941 -0.00484
AFIX 43
H53 2 0.474142 0.789394 0.734592 11.00000 -1.20000
AFIX 0
C54 1 0.579342 0.776451 0.808645 11.00000 0.02534 0.03009 =
0.04418 0.00056 -0.01172 -0.01065
AFIX 43
H54 2 0.636608 0.817370 0.783458 11.00000 -1.20000
AFIX 0
C55 1 0.591921 0.733902 0.874428 11.00000 0.03017 0.02969 =
0.04982 -0.00666 -0.02473 -0.00346
AFIX 43
H55 2 0.658231 0.745317 0.894286 11.00000 -1.20000
AFIX 0
C56 1 0.508210 0.674755 0.911404 11.00000 0.04191 0.02748 =
0.03911 0.00259 -0.02532 -0.00448
AFIX 43
H56 2 0.516196 0.646112 0.957055 11.00000 -1.20000
AFIX 0
C57 1 0.412705 0.657386 0.881712 11.00000 0.03165 0.02141 =
0.03230 0.00298 -0.01423 -0.00766
AFIX 43
H57 2 0.355659 0.616568 0.907431 11.00000 -1.20000
AFIX 0
B4 3 0.156704 0.569862 0.752758 11.00000 0.01759 0.01737 =
0.01984 -0.00039 -0.00550 -0.00199
B5 3 0.186066 0.710470 0.684661 11.00000 0.01628 0.02072 =
0.01911 -0.00071 -0.00229 -0.00064
B6 3 0.296086 0.674043 0.777161 11.00000 0.01789 0.01888 =
0.02091 -0.00194 -0.00426 -0.00045
N2 4 0.228214 -0.047976 0.839165 11.00000 0.03237 0.03152 =
0.02978 0.00272 -0.00676 -0.01309
H2A 2 0.220632 -0.048708 0.791359 11.00000 0.05846
H2B 2 0.274377 -0.103080 0.844947 11.00000 0.05787
C26 1 0.103275 -0.043803 0.898166 11.00000 0.02512 0.02322 =
0.04812 -0.00368 -0.00858 -0.00504
AFIX 23
H26A 2 0.047609 0.003223 0.883703 11.00000 -1.20000
H26B 2 0.111289 -0.026074 0.949301 11.00000 -1.20000
AFIX 0
C27 1 0.040139 -0.128299 0.908552 11.00000 0.01628 0.01927 =
0.04234 -0.00610 -0.00277 -0.00065
C28 1 0.015755 -0.171487 0.979048 11.00000 0.02266 0.02839 =
0.04015 -0.00577 -0.00587 0.00093
AFIX 43
H28 2 0.041118 -0.148601 1.020316 11.00000 -1.20000
AFIX 0
C29 1 -0.045328 -0.247850 0.990156 11.00000 0.02947 0.02591 =
0.04372 0.00206 0.00195 0.00150
AFIX 43
H29 2 -0.061561 -0.276772 1.038820 11.00000 -1.20000
AFIX 0
C30 1 -0.082457 -0.281743 0.930553 11.00000 0.02591 0.01934 =
0.05680 -0.00862 0.00425 -0.00450
AFIX 43
H30 2 -0.125545 -0.333365 0.938364 11.00000 -1.20000
AFIX 0
C31 1 -0.056602 -0.240167 0.859449 11.00000 0.02490 0.02615 =
0.04581 -0.01437 -0.00273 -0.00269
AFIX 43
H31 2 -0.080718 -0.263858 0.817988 11.00000 -1.20000
AFIX 0
C32 1 0.004380 -0.164042 0.848463 11.00000 0.02384 0.02400 =
0.03716 -0.00509 -0.00161 -0.00073
AFIX 43
H32 2 0.021954 -0.135963 0.799368 11.00000 -1.20000
AFIX 0
N4 4 0.061235 0.427351 0.618482 11.00000 0.03462 0.03592 =
0.02751 0.00746 -0.01044 -0.01615
H4A 2 0.020164 0.391990 0.655630 11.00000 0.05126
H4B 2 0.000726 0.472315 0.613345 11.00000 0.05239
C58 1 0.109961 0.375039 0.545238 11.00000 0.04363 0.02595 =
0.03386 0.00350 -0.01769 -0.01208
AFIX 23
H58A 2 0.039671 0.348504 0.534602 11.00000 -1.20000
H58B 2 0.170900 0.326157 0.551482 11.00000 -1.20000
AFIX 0
C59 1 0.173597 0.428596 0.475893 11.00000 0.02463 0.02531 =
0.02843 0.00120 -0.01416 -0.00253
C60 1 0.226997 0.386788 0.402700 11.00000 0.04008 0.03073 =
0.03408 -0.00434 -0.01912 0.00130
AFIX 43
H60 2 0.221793 0.325316 0.397094 11.00000 -1.20000
AFIX 0
C61 1 0.287514 0.433286 0.337999 11.00000 0.03349 0.05162 =
0.02592 -0.00458 -0.01161 0.00402
AFIX 43
H61 2 0.324198 0.403555 0.288537 11.00000 -1.20000
AFIX 0
C62 1 0.294843 0.522953 0.345023 11.00000 0.02708 0.05175 =
0.02902 0.01097 -0.00973 -0.00921
AFIX 43
H62 2 0.335690 0.555132 0.300492 11.00000 -1.20000
AFIX 0
C63 1 0.242239 0.565288 0.417367 11.00000 0.02948 0.03201 =
0.03742 0.00655 -0.01238 -0.00939
AFIX 43
H63 2 0.247295 0.626835 0.422609 11.00000 -1.20000
AFIX 0
C64 1 0.182013 0.518542 0.482494 11.00000 0.02424 0.02664 =
0.02783 0.00028 -0.00841 -0.00381
AFIX 43
H64 2 0.146262 0.548346 0.531990 11.00000 -1.20000
AFIX 0
HKLF 4
REM 15srv282 in P-1 #2
REM R1 = 0.0445 for 10461 Fo > 4sig(Fo) and 0.0624 for all 13416 data
REM 753 parameters refined using 0 restraints
END
WGHT 0.0430 0.9444
REM Highest difference peak 0.332, deepest hole -0.293, 1-sigma level 0.045
Q1 1 0.0955 0.5410 0.7777 11.00000 0.05 0.33
Q2 1 0.3396 0.6918 0.7987 11.00000 0.05 0.31
Q3 1 0.4798 0.0423 0.6797 11.00000 0.05 0.28
Q4 1 0.3782 0.2168 0.8378 11.00000 0.05 0.27
Q5 1 0.1548 0.7486 0.6588 11.00000 0.05 0.27
Q6 1 0.1581 0.1721 0.7287 11.00000 0.05 0.26
Q7 1 0.1459 0.1579 0.7440 11.00000 0.05 0.25
Q8 1 0.0640 -0.0892 0.9086 11.00000 0.05 0.21
Q9 1 0.3569 0.2922 0.8802 11.00000 0.05 0.20
Q10 1 0.1445 0.4068 0.5116 11.00000 0.05 0.20
REM The information below was added by Olex2.
REM
REM R1 = 0.0445 for 10461 Fo > 4sig(Fo) and 0.0624 for all 55371 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.33, deepest hole -0.29
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0624
REM R1_gt = 0.0445
REM wR_ref = 0.1087
REM GOOF = 1.030
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 55371
REM Reflections_gt = 10461
REM Parameters = n/a
REM Hole = -0.29
REM Peak = 0.33
REM Flack = n/a
;
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_7a_14srv233
_database_code_depnum_ccdc_archive 'CCDC 1563949'
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date 2017-07-23
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number 2016/6
_chemical_name_common ?
_chemical_name_systematic 3,4,5-trifluorophenylboroxine
_chemical_formula_moiety 'C18 H6 B3 F9 O3'
_chemical_formula_sum 'C18 H6 B3 F9 O3'
_chemical_formula_weight 473.66
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 12.8086(4)
_cell_length_b 12.6262(4)
_cell_length_c 12.8625(5)
_cell_angle_alpha 90
_cell_angle_beta 119.598(2)
_cell_angle_gamma 90
_cell_volume 1808.74(12)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3537
_cell_measurement_temperature 220
_cell_measurement_theta_max 75.088
_cell_measurement_theta_min 3.95
_shelx_estimated_absorpt_T_max 0.826
_shelx_estimated_absorpt_T_min 0.564
_exptl_absorpt_coefficient_mu 1.579
_exptl_absorpt_correction_T_max 0.7539
_exptl_absorpt_correction_T_min 0.5487
_exptl_absorpt_correction_type integration
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0927 after correction.
The Ratio of minimum to maximum transmission is 0.7278.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.739
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description trapetsoid
_exptl_crystal_F_000 936
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 0.0160
1.00 0.00 0.00 0.0630
-1.00 3.00 0.00 0.0830
1.00 0.00 -1.00 0.2010
1.00 1.00 0.00 0.0930
-1.00 -1.00 0.00 0.0750
1.00 -3.00 -1.00 0.1170
-1.00 3.00 1.00 0.1150
1.00 -3.00 0.00 0.0950
0.00 0.00 1.00 0.1410
0.00 0.00 -1.00 0.1540
_exptl_crystal_size_max 0.409
_exptl_crystal_size_mid 0.209
_exptl_crystal_size_min 0.126
_exptl_special_details
;
The data collection nominally covered full sphere of reciprocal
space, by a combination of 7 runs of narrow-frame \w-scans (scan
width 0.5\% \w, 3s exposure for 3 low-\q runs, 6s for 4 high-\q runs),
every run at a different 2\q and/or \f angle. Crystal to detector
distance 3.50 cm.
Phase transition on cooling below 210 K.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0536
_diffrn_reflns_av_unetI/netI 0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 6438
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full 66.000
_diffrn_reflns_theta_max 75.320
_diffrn_reflns_theta_min 5.296
_diffrn_ambient_temperature 220
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method \w-scan
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Incoatec I\mS microsource'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 1418
_reflns_number_total 1790
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL 2016/6 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max 0.397
_refine_diff_density_min -0.272
_refine_diff_density_rms 0.081
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 152
_refine_ls_number_reflns 1790
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0715
_refine_ls_R_factor_gt 0.0628
_refine_ls_restrained_S_all 1.053
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1380P)^2^+0.0940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1811
_refine_ls_wR_factor_ref 0.1941
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
C3(H3), C6(H6), C10(H10)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.500000 1.24897(15) 0.250000 0.0848(6) Uani 1 2 d S T P . .
F2 F 0.44542(16) 1.14318(11) 0.39804(14) 0.0867(5) Uani 1 1 d . . . . .
F3 F 0.26021(14) 0.62852(13) 0.55967(14) 0.0839(5) Uani 1 1 d . . . . .
F4 F 0.23531(12) 0.41784(12) 0.53955(13) 0.0773(5) Uani 1 1 d . . . . .
F5 F 0.30137(15) 0.30961(11) 0.40274(15) 0.0851(5) Uani 1 1 d . . . . .
O1 O 0.45204(12) 0.74488(12) 0.30892(11) 0.0589(4) Uani 1 1 d . . . . .
O2 O 0.500000 0.58135(15) 0.250000 0.0553(5) Uani 1 2 d S T P . .
C1 C 0.500000 1.1430(2) 0.250000 0.0626(7) Uani 1 2 d S T P . .
C2 C 0.47108(19) 1.08739(18) 0.32481(19) 0.0622(5) Uani 1 1 d . . . . .
C3 C 0.46917(17) 0.97852(17) 0.32450(16) 0.0582(5) Uani 1 1 d . . . . .
H3 H 0.447147 0.941883 0.374358 0.070 Uiso 1 1 calc R . . . .
C4 C 0.500000 0.9225(2) 0.250000 0.0529(6) Uani 1 2 d S T P . .
C5 C 0.38451(16) 0.57557(15) 0.36404(16) 0.0534(5) Uani 1 1 d . . . . .
C6 C 0.34690(19) 0.63131(16) 0.43379(18) 0.0591(5) Uani 1 1 d . . . . .
H6 H 0.355898 0.705257 0.441460 0.071 Uiso 1 1 calc R . . . .
C7 C 0.29675(19) 0.57719(18) 0.49092(19) 0.0612(5) Uani 1 1 d . . . . .
C8 C 0.28253(17) 0.46934(18) 0.48158(18) 0.0601(6) Uani 1 1 d . . . . .
C9 C 0.31780(19) 0.41485(17) 0.41092(19) 0.0607(5) Uani 1 1 d . . . . .
C10 C 0.36906(17) 0.46612(16) 0.35295(17) 0.0564(5) Uani 1 1 d . . . . .
H10 H 0.393528 0.427596 0.306146 0.068 Uiso 1 1 calc R . . . .
B1 B 0.500000 0.7998(3) 0.250000 0.0554(7) Uani 1 2 d S T P . .
B2 B 0.44711(18) 0.63597(19) 0.30444(17) 0.0532(5) 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 0.1079(16) 0.0610(10) 0.1088(15) 0.000 0.0713(13) 0.000
F2 0.1195(13) 0.0765(9) 0.1039(11) -0.0114(7) 0.0856(10) 0.0021(8)
F3 0.1019(11) 0.0965(11) 0.0919(10) -0.0028(7) 0.0774(9) 0.0074(8)
F4 0.0686(8) 0.0982(11) 0.0821(9) 0.0198(6) 0.0503(7) -0.0038(6)
F5 0.0947(10) 0.0651(8) 0.1120(12) 0.0023(6) 0.0637(9) -0.0079(7)
O1 0.0657(9) 0.0637(8) 0.0649(9) -0.0023(5) 0.0457(7) -0.0016(6)
O2 0.0556(10) 0.0639(11) 0.0596(10) 0.000 0.0386(8) 0.000
C1 0.0648(16) 0.0580(15) 0.0727(17) 0.000 0.0397(14) 0.000
C2 0.0647(11) 0.0703(13) 0.0662(12) -0.0068(8) 0.0436(10) 0.0004(9)
C3 0.0589(11) 0.0684(13) 0.0584(11) 0.0011(8) 0.0373(9) -0.0008(8)
C4 0.0476(12) 0.0655(15) 0.0523(13) 0.000 0.0299(10) 0.000
C5 0.0472(9) 0.0670(11) 0.0535(10) 0.0010(7) 0.0307(8) 0.0016(8)
C6 0.0606(11) 0.0660(11) 0.0639(11) 0.0006(8) 0.0407(9) 0.0022(9)
C7 0.0586(10) 0.0790(13) 0.0623(11) 0.0010(9) 0.0423(9) 0.0040(9)
C8 0.0494(10) 0.0811(14) 0.0586(11) 0.0114(9) 0.0333(8) -0.0017(9)
C9 0.0545(10) 0.0623(11) 0.0677(12) 0.0042(8) 0.0320(9) -0.0021(8)
C10 0.0521(10) 0.0676(12) 0.0573(10) -0.0013(8) 0.0328(8) 0.0012(8)
B1 0.0529(15) 0.0659(17) 0.0537(15) 0.000 0.0311(12) 0.000
B2 0.0476(10) 0.0666(13) 0.0514(11) 0.0007(8) 0.0290(8) 0.0009(8)
_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 C1 1.338(4) . ?
F2 C2 1.341(2) . ?
F3 C7 1.353(2) . ?
F4 C8 1.338(2) . ?
F5 C9 1.341(3) . ?
O1 B1 1.376(2) . ?
O1 B2 1.376(3) . ?
O2 B2 1.376(2) 2_655 ?
O2 B2 1.376(2) . ?
C1 C2 1.381(3) . ?
C1 C2 1.381(3) 2_655 ?
C2 C3 1.375(3) . ?
C3 C4 1.396(2) . ?
C4 B1 1.549(4) . ?
C5 C6 1.400(3) . ?
C5 C10 1.393(3) . ?
C5 B2 1.555(3) . ?
C6 C7 1.373(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.375(3) . ?
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
B1 O1 B2 120.29(17) . . ?
B2 O2 B2 119.8(2) . 2_655 ?
F1 C1 C2 120.54(14) . . ?
F1 C1 C2 120.54(14) . 2_655 ?
C2 C1 C2 118.9(3) . 2_655 ?
F2 C2 C1 117.8(2) . . ?
F2 C2 C3 121.15(18) . . ?
C3 C2 C1 121.10(19) . . ?
C2 C3 C4 119.88(18) . . ?
C3 C4 C3 119.1(3) . 2_655 ?
C3 C4 B1 120.46(13) . . ?
C3 C4 B1 120.46(13) 2_655 . ?
C6 C5 B2 119.59(18) . . ?
C10 C5 C6 119.20(17) . . ?
C10 C5 B2 121.17(17) . . ?
C7 C6 C5 119.53(19) . . ?
F3 C7 C6 121.05(19) . . ?
F3 C7 C8 117.33(18) . . ?
C8 C7 C6 121.61(18) . . ?
F4 C8 C7 120.72(19) . . ?
F4 C8 C9 120.6(2) . . ?
C7 C8 C9 118.66(18) . . ?
F5 C9 C8 117.08(18) . . ?
F5 C9 C10 121.49(19) . . ?
C10 C9 C8 121.4(2) . . ?
C9 C10 C5 119.56(18) . . ?
O1 B1 O1 119.4(3) . 2_655 ?
O1 B1 C4 120.28(13) 2_655 . ?
O1 B1 C4 120.28(13) . . ?
O1 B2 C5 119.56(17) . . ?
O2 B2 O1 119.87(17) . . ?
O2 B2 C5 120.5(2) . . ?
_shelx_res_file
;
TITL 14srv233 in C 2yc #-1
14srv233.res
created by SHELXL-2016/6 at 03:40:16 on 23-Jul-2017
REM reset to C 2yc #-1
CELL 1.54184 12.80862 12.62621 12.86254 90 119.5984 90
ZERR 4 0.00042 0.00042 0.0005 0 0.0023 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H B F O
UNIT 72 24 12 36 12
L.S. 7
PLAN 5
SIZE 0.126 0.209 0.409
TEMP -53.15
BOND
fmap 2
acta 132
OMIT -13 1 8
REM
REM
REM
WGHT 0.138000 0.094000
FVAR 0.44735
F1 4 0.500000 1.248974 0.250000 10.50000 0.10786 0.06101 =
0.10879 0.00000 0.07132 0.00000
F2 4 0.445416 1.143179 0.398042 11.00000 0.11952 0.07646 =
0.10392 -0.01138 0.08560 0.00214
F3 4 0.260213 0.628517 0.559670 11.00000 0.10192 0.09653 =
0.09190 -0.00279 0.07745 0.00736
F4 4 0.235312 0.417836 0.539552 11.00000 0.06861 0.09825 =
0.08213 0.01978 0.05033 -0.00378
F5 4 0.301372 0.309606 0.402737 11.00000 0.09468 0.06509 =
0.11202 0.00229 0.06373 -0.00791
O1 5 0.452037 0.744878 0.308915 11.00000 0.06572 0.06375 =
0.06491 -0.00231 0.04567 -0.00160
O2 5 0.500000 0.581347 0.250000 10.50000 0.05565 0.06389 =
0.05960 0.00000 0.03856 0.00000
C1 1 0.500000 1.142975 0.250000 10.50000 0.06479 0.05801 =
0.07266 0.00000 0.03972 0.00000
C2 1 0.471084 1.087393 0.324812 11.00000 0.06466 0.07032 =
0.06622 -0.00680 0.04357 0.00042
C3 1 0.469173 0.978516 0.324496 11.00000 0.05889 0.06838 =
0.05835 0.00109 0.03730 -0.00080
AFIX 43
H3 2 0.447147 0.941883 0.374358 11.00000 -1.20000
AFIX 0
C4 1 0.500000 0.922468 0.250000 10.50000 0.04761 0.06548 =
0.05232 0.00000 0.02991 0.00000
C5 1 0.384513 0.575570 0.364040 11.00000 0.04720 0.06696 =
0.05352 0.00104 0.03067 0.00156
C6 1 0.346898 0.631307 0.433787 11.00000 0.06056 0.06599 =
0.06393 0.00064 0.04074 0.00222
AFIX 43
H6 2 0.355898 0.705257 0.441460 11.00000 -1.20000
AFIX 0
C7 1 0.296754 0.577194 0.490924 11.00000 0.05858 0.07902 =
0.06230 0.00100 0.04231 0.00399
C8 1 0.282531 0.469338 0.481582 11.00000 0.04938 0.08106 =
0.05857 0.01142 0.03334 -0.00168
C9 1 0.317798 0.414851 0.410917 11.00000 0.05445 0.06230 =
0.06773 0.00421 0.03203 -0.00206
C10 1 0.369062 0.466120 0.352951 11.00000 0.05208 0.06756 =
0.05729 -0.00134 0.03285 0.00118
AFIX 43
H10 2 0.393528 0.427596 0.306146 11.00000 -1.20000
AFIX 0
B1 3 0.500000 0.799822 0.250000 10.50000 0.05290 0.06589 =
0.05368 0.00000 0.03114 0.00000
B2 3 0.447112 0.635967 0.304439 11.00000 0.04756 0.06657 =
0.05140 0.00072 0.02903 0.00086
HKLF 4 1 -1 0 0 0 -1 0 1 0 1
REM 14srv233 in C 2yc #-1
REM R1 = 0.0628 for 1418 Fo > 4sig(Fo) and 0.0715 for all 1790 data
REM 152 parameters refined using 0 restraints
END
WGHT 0.1387 0.0937
REM Highest difference peak 0.397, deepest hole -0.272, 1-sigma level 0.081
Q1 1 0.5000 0.6309 0.2500 10.50000 0.05 0.40
Q2 1 0.2174 0.3629 0.4043 11.00000 0.05 0.28
Q3 1 0.5555 0.7026 0.2981 11.00000 0.05 0.24
Q4 1 0.2760 0.2202 0.4711 11.00000 0.05 0.23
Q5 1 0.5000 0.7053 0.2500 10.50000 0.05 0.23
;
_shelx_res_checksum 15905
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'