# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014
#######################################################################
#
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# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
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data_shelxl
_audit_creation_date 2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C37 H64 B N3, C2.5 H5.5'
_chemical_formula_sum 'C39.50 H70 B N3'
_chemical_formula_weight 597.80
_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'
_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
_cell_length_a 27.415(5)
_cell_length_b 18.243(4)
_cell_length_c 17.305(3)
_cell_angle_alpha 90.00
_cell_angle_beta 114.471(2)
_cell_angle_gamma 90.00
_cell_volume 7877(3)
_cell_formula_units_Z 8
_cell_measurement_reflns_used ?
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max ?
_cell_measurement_theta_min ?
_exptl_absorpt_coefficient_mu 0.057
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.008
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description ?
_exptl_crystal_F_000 2664
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.15
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0609
_diffrn_reflns_av_unetI/netI 0.0878
_diffrn_reflns_limit_h_max 39
_diffrn_reflns_limit_h_min -43
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 32951
_diffrn_reflns_theta_full 34.36
_diffrn_reflns_theta_max 34.36
_diffrn_reflns_theta_min 2.11
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 9443
_reflns_number_total 15374
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.932
_refine_diff_density_min -0.463
_refine_diff_density_rms 0.054
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 587
_refine_ls_number_reflns 15374
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1173
_refine_ls_R_factor_gt 0.0629
_refine_ls_restrained_S_all 1.020
_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^)+(0.0961P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1547
_refine_ls_wR_factor_ref 0.1813
_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
;
1. Others
Fixed Sof: H3S1(0.5) H3S2(0.5)
Fixed U12: C3S(0)
Fixed U23: C3S(0)
Fixed Uiso: H1S1(0.207) H1S2(0.207) H1S3(0.207) H2S1(0.105) H2S2(0.105)
H3S1(0.087) H3S2(0.087)
Fixed X: H1S1(0.5033) H1S2(0.5605) H1S3(0.5562) H2S1(0.5609) H2S2(0.5778)
C3S(0.5) H3S1(0.5104) H3S2(0.4896)
Fixed Y: H1S1(0.0349) H1S2(-0.0012) H1S3(0.0683) H2S1(0.0682) H2S2(0.133)
H3S1(0.1728) H3S2(0.1728)
Fixed Z: H1S1(0.1487) H1S2(0.2037) H1S3(0.1447) H2S1(0.3103) H2S2(0.2645)
C3S(0.25) H3S1(0.3004) H3S2(0.1996)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85972(4) 0.15587(6) 0.39362(6) 0.01496(18) Uani 1 1 d . . .
N2 N 0.68216(4) 0.14362(6) 0.02210(6) 0.0183(2) Uani 1 1 d . . .
N3 N 0.64937(4) 0.27784(6) 0.15887(6) 0.01707(19) Uani 1 1 d . . .
B1 B 0.78710(5) 0.17992(8) 0.24760(8) 0.0159(2) Uani 1 1 d . . .
C1 C 0.72931(5) 0.19152(6) 0.17885(7) 0.0154(2) Uani 1 1 d . . .
C2 C 0.67994(4) 0.22765(6) 0.14443(7) 0.0151(2) Uani 1 1 d . . .
C3 C 0.69278(5) 0.17889(6) 0.09452(7) 0.0156(2) Uani 1 1 d . . .
C4 C 0.80434(4) 0.16099(6) 0.33760(7) 0.01375(19) Uani 1 1 d . . .
C5 C 0.77347(4) 0.13304(6) 0.38833(7) 0.01371(19) Uani 1 1 d . . .
C6 C 0.81580(5) 0.13622(7) 0.48123(7) 0.0158(2) Uani 1 1 d . . .
C7 C 0.87100(5) 0.12720(7) 0.47921(7) 0.0166(2) Uani 1 1 d . . .
C8 C 0.89979(4) 0.18961(7) 0.37328(7) 0.0153(2) Uani 1 1 d . . .
C9 C 0.93047(5) 0.14700(7) 0.34179(7) 0.0180(2) Uani 1 1 d . . .
C10 C 0.97165(5) 0.18087(8) 0.32737(7) 0.0223(3) Uani 1 1 d . . .
C11 C 0.98120(5) 0.25524(9) 0.33946(8) 0.0241(3) Uani 1 1 d . . .
C12 C 0.94896(5) 0.29770(8) 0.36561(8) 0.0216(2) Uani 1 1 d . . .
C13 C 0.90815(5) 0.26606(7) 0.38325(7) 0.0174(2) Uani 1 1 d . . .
C14 C 0.72557(5) 0.18161(7) 0.37833(7) 0.0162(2) Uani 1 1 d . . .
C15 C 0.69592(5) 0.15758(8) 0.43205(8) 0.0222(2) Uani 1 1 d . . .
C16 C 0.75492(5) 0.05251(7) 0.36449(8) 0.0190(2) Uani 1 1 d . . .
C17 C 0.70512(6) 0.04119(8) 0.28231(9) 0.0248(3) Uani 1 1 d . . .
C18 C 0.91424(5) 0.17116(9) 0.54991(7) 0.0229(3) Uani 1 1 d . . .
C19 C 0.88931(6) 0.04664(8) 0.49118(8) 0.0234(3) Uani 1 1 d . . .
C20 C 0.91828(5) 0.06689(8) 0.31817(8) 0.0218(2) Uani 1 1 d . . .
C21 C 0.96636(6) 0.01727(10) 0.36512(10) 0.0316(3) Uani 1 1 d . . .
C22 C 0.89890(6) 0.05639(9) 0.22176(9) 0.0278(3) Uani 1 1 d . . .
C23 C 0.87365(5) 0.31611(7) 0.41001(8) 0.0200(2) Uani 1 1 d . . .
C24 C 0.90696(6) 0.36601(8) 0.48445(9) 0.0278(3) Uani 1 1 d . . .
C25 C 0.83718(6) 0.36265(8) 0.33438(10) 0.0277(3) Uani 1 1 d . . .
C26 C 0.72289(5) 0.09345(7) 0.01600(8) 0.0212(2) Uani 1 1 d . . .
C27 C 0.77088(6) 0.13576(10) 0.01720(9) 0.0293(3) Uani 1 1 d . . .
C28 C 0.73929(6) 0.03449(8) 0.08456(9) 0.0268(3) Uani 1 1 d . . .
C29 C 0.63005(5) 0.15052(8) -0.05145(7) 0.0218(2) Uani 1 1 d . . .
C30 C 0.59872(7) 0.07919(10) -0.06759(13) 0.0406(4) Uani 1 1 d . . .
C31 C 0.63636(7) 0.17761(12) -0.12985(9) 0.0372(4) Uani 1 1 d . . .
C32 C 0.67532(5) 0.32450(7) 0.23472(7) 0.0177(2) Uani 1 1 d . . .
C33 C 0.64174(6) 0.32868(9) 0.28604(9) 0.0266(3) Uani 1 1 d . . .
C34 C 0.68809(6) 0.40026(8) 0.21145(9) 0.0261(3) Uani 1 1 d . . .
C35 C 0.59659(5) 0.29979(8) 0.09324(8) 0.0226(3) Uani 1 1 d . . .
C36 C 0.55731(6) 0.23634(10) 0.07274(10) 0.0312(3) Uani 1 1 d . . .
C37 C 0.60065(6) 0.33406(9) 0.01565(9) 0.0276(3) Uani 1 1 d . . .
C1S C 0.54148(16) 0.0450(3) 0.1815(4) 0.1381(19) Uani 1 1 d . . .
H1S1 H 0.5033 0.0349 0.1487 0.207 Uiso 1 1 calc R . .
H1S2 H 0.5605 -0.0012 0.2037 0.207 Uiso 1 1 calc R . .
H1S3 H 0.5562 0.0683 0.1447 0.207 Uiso 1 1 calc R . .
C2S C 0.54880(12) 0.09779(19) 0.2577(2) 0.0872(9) Uani 1 1 d . . .
H2S1 H 0.5609 0.0682 0.3103 0.105 Uiso 1 1 calc R . .
H2S2 H 0.5778 0.1330 0.2645 0.105 Uiso 1 1 calc R . .
C3S C 0.5000 0.1406(2) 0.2500 0.0728(10) Uani 1 2 d S . .
H3S1 H 0.5104 0.1728 0.3004 0.087 Uiso 0.50 1 calc PR . .
H3S2 H 0.4896 0.1728 0.1996 0.087 Uiso 0.50 1 calc PR . .
H6A H 0.8127(7) 0.1870(12) 0.5039(13) 0.0327(6) Uiso 1 1 d . . .
H6B H 0.8079(7) 0.1007(11) 0.5167(13) 0.0327(6) Uiso 1 1 d . . .
H10 H 0.9938(7) 0.1511(11) 0.3059(13) 0.0327(6) Uiso 1 1 d . . .
H11 H 1.0102(8) 0.2774(11) 0.3294(12) 0.0327(6) Uiso 1 1 d . . .
H12 H 0.9551(7) 0.3510(12) 0.3734(12) 0.0327(6) Uiso 1 1 d . . .
H14A H 0.7382(7) 0.2314(12) 0.3925(12) 0.0327(6) Uiso 1 1 d . . .
H14B H 0.7012(7) 0.1836(11) 0.3174(13) 0.0327(6) Uiso 1 1 d . . .
H15A H 0.6805(7) 0.1071(12) 0.4152(12) 0.0327(6) Uiso 1 1 d . . .
H15B H 0.6641(7) 0.1902(11) 0.4216(12) 0.0327(6) Uiso 1 1 d . . .
H15C H 0.7200(8) 0.1563(11) 0.4934(13) 0.0327(6) Uiso 1 1 d . . .
H16A H 0.7848(7) 0.0249(11) 0.3610(12) 0.0327(6) Uiso 1 1 d . . .
H16B H 0.7489(7) 0.0275(11) 0.4127(12) 0.0327(6) Uiso 1 1 d . . .
H17A H 0.6723(7) 0.0641(11) 0.2866(13) 0.0327(6) Uiso 1 1 d . . .
H17B H 0.6982(7) -0.0102(12) 0.2693(12) 0.0327(6) Uiso 1 1 d . . .
H17C H 0.7111(7) 0.0621(11) 0.2355(13) 0.0327(6) Uiso 1 1 d . . .
H18A H 0.9471(8) 0.1704(11) 0.5418(12) 0.0327(6) Uiso 1 1 d . . .
H18B H 0.9200(7) 0.1474(11) 0.6065(12) 0.0327(6) Uiso 1 1 d . . .
H18C H 0.9038(7) 0.2243(12) 0.5492(12) 0.0327(6) Uiso 1 1 d . . .
H19A H 0.8638(7) 0.0139(11) 0.4449(12) 0.0327(6) Uiso 1 1 d . . .
H19B H 0.8925(7) 0.0273(11) 0.5447(13) 0.0327(6) Uiso 1 1 d . . .
H19C H 0.9235(8) 0.0424(11) 0.4905(12) 0.0327(6) Uiso 1 1 d . . .
H20 H 0.8885(7) 0.0541(11) 0.3335(13) 0.0327(6) Uiso 1 1 d . . .
H21A H 0.9926(7) 0.0246(11) 0.3425(12) 0.0327(6) Uiso 1 1 d . . .
H21B H 0.9554(7) -0.0350(12) 0.3520(12) 0.0327(6) Uiso 1 1 d . . .
H21C H 0.9833(7) 0.0281(11) 0.4291(13) 0.0327(6) Uiso 1 1 d . . .
H22A H 0.8677(8) 0.0856(11) 0.1880(13) 0.0327(6) Uiso 1 1 d . . .
H22B H 0.8886(7) 0.0034(12) 0.2050(12) 0.0327(6) Uiso 1 1 d . . .
H22C H 0.9269(7) 0.0690(11) 0.2005(13) 0.0327(6) Uiso 1 1 d . . .
H23 H 0.8521(7) 0.2854(11) 0.4280(12) 0.0327(6) Uiso 1 1 d . . .
H24A H 0.9336(7) 0.3377(11) 0.5365(13) 0.0327(6) Uiso 1 1 d . . .
H24B H 0.8795(7) 0.3972(11) 0.5034(13) 0.0327(6) Uiso 1 1 d . . .
H24C H 0.9296(7) 0.4026(11) 0.4681(13) 0.0327(6) Uiso 1 1 d . . .
H25A H 0.8583(8) 0.3941(11) 0.3163(13) 0.0327(6) Uiso 1 1 d . . .
H25B H 0.8145(8) 0.3918(11) 0.3514(13) 0.0327(6) Uiso 1 1 d . . .
H25C H 0.8155(8) 0.3317(11) 0.2893(13) 0.0327(6) Uiso 1 1 d . . .
H26 H 0.7037(7) 0.0689(11) -0.0415(13) 0.0327(6) Uiso 1 1 d . . .
H27A H 0.7613(7) 0.1706(11) -0.0278(13) 0.0327(6) Uiso 1 1 d . . .
H27B H 0.7966(8) 0.1045(11) 0.0098(13) 0.0327(6) Uiso 1 1 d . . .
H27C H 0.7895(8) 0.1616(11) 0.0723(13) 0.0327(6) Uiso 1 1 d . . .
H28A H 0.7598(7) 0.0568(11) 0.1409(13) 0.0327(6) Uiso 1 1 d . . .
H28B H 0.7633(7) -0.0002(11) 0.0731(12) 0.0327(6) Uiso 1 1 d . . .
H28C H 0.7069(7) 0.0062(11) 0.0802(12) 0.0327(6) Uiso 1 1 d . . .
H29 H 0.6116(7) 0.1887(11) -0.0355(12) 0.0327(6) Uiso 1 1 d . . .
H30A H 0.6167(7) 0.0411(12) -0.0840(13) 0.0327(6) Uiso 1 1 d . . .
H30B H 0.5637(8) 0.0884(11) -0.1110(13) 0.0327(6) Uiso 1 1 d . . .
H30C H 0.5954(7) 0.0620(11) -0.0139(13) 0.0327(6) Uiso 1 1 d . . .
H31A H 0.6554(8) 0.2255(12) -0.1176(12) 0.0327(6) Uiso 1 1 d . . .
H31B H 0.6011(8) 0.1877(11) -0.1753(13) 0.0327(6) Uiso 1 1 d . . .
H31C H 0.6561(8) 0.1450(12) -0.1456(13) 0.0327(6) Uiso 1 1 d . . .
H32 H 0.7097(7) 0.3000(11) 0.2694(13) 0.0327(6) Uiso 1 1 d . . .
H33A H 0.6077(8) 0.3568(11) 0.2555(13) 0.0327(6) Uiso 1 1 d . . .
H33B H 0.6622(7) 0.3514(11) 0.3395(13) 0.0327(6) Uiso 1 1 d . . .
H33C H 0.6350(7) 0.2812(12) 0.3002(12) 0.0327(6) Uiso 1 1 d . . .
H34A H 0.7096(7) 0.3976(11) 0.1790(13) 0.0327(6) Uiso 1 1 d . . .
H34B H 0.7080(7) 0.4284(11) 0.2619(13) 0.0327(6) Uiso 1 1 d . . .
H34C H 0.6549(8) 0.4262(11) 0.1787(13) 0.0327(6) Uiso 1 1 d . . .
H35 H 0.5832(7) 0.3395(11) 0.1221(12) 0.0327(6) Uiso 1 1 d . . .
H36A H 0.5687(7) 0.1942(12) 0.0494(13) 0.0327(6) Uiso 1 1 d . . .
H36B H 0.5238(8) 0.2525(11) 0.0321(13) 0.0327(6) Uiso 1 1 d . . .
H36C H 0.5522(7) 0.2206(11) 0.1221(13) 0.0327(6) Uiso 1 1 d . . .
H37A H 0.6233(7) 0.3770(12) 0.0315(12) 0.0327(6) Uiso 1 1 d . . .
H37B H 0.5644(8) 0.3470(11) -0.0240(13) 0.0327(6) Uiso 1 1 d . . .
H37C H 0.6165(7) 0.2995(11) -0.0099(13) 0.0327(6) Uiso 1 1 d . . .
H1 H 0.8168(7) 0.1854(11) 0.2199(13) 0.0327(6) 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
N1 0.0120(4) 0.0212(5) 0.0111(4) 0.0031(3) 0.0043(3) 0.0007(4)
N2 0.0182(5) 0.0213(5) 0.0121(4) -0.0036(3) 0.0030(3) 0.0031(4)
N3 0.0133(4) 0.0199(5) 0.0149(4) -0.0035(3) 0.0028(3) 0.0017(4)
B1 0.0140(5) 0.0211(6) 0.0124(5) 0.0004(4) 0.0052(4) 0.0009(5)
C1 0.0157(5) 0.0178(5) 0.0131(4) -0.0006(4) 0.0063(4) -0.0010(4)
C2 0.0142(5) 0.0171(5) 0.0126(4) -0.0011(4) 0.0042(4) -0.0009(4)
C3 0.0155(5) 0.0173(5) 0.0125(4) -0.0003(4) 0.0044(4) -0.0002(4)
C4 0.0117(4) 0.0163(5) 0.0127(4) -0.0005(4) 0.0046(4) 0.0002(4)
C5 0.0132(5) 0.0162(5) 0.0120(4) -0.0011(4) 0.0054(4) -0.0004(4)
C6 0.0165(5) 0.0189(5) 0.0128(4) 0.0003(4) 0.0069(4) -0.0002(4)
C7 0.0148(5) 0.0219(6) 0.0118(4) 0.0031(4) 0.0042(4) 0.0007(4)
C8 0.0113(4) 0.0223(6) 0.0110(4) 0.0022(4) 0.0032(4) 0.0011(4)
C9 0.0137(5) 0.0272(6) 0.0119(4) 0.0018(4) 0.0041(4) 0.0024(4)
C10 0.0144(5) 0.0375(7) 0.0158(5) 0.0003(5) 0.0071(4) 0.0015(5)
C11 0.0144(5) 0.0404(8) 0.0172(5) 0.0020(5) 0.0064(4) -0.0058(5)
C12 0.0179(5) 0.0287(7) 0.0162(5) 0.0027(4) 0.0050(4) -0.0049(5)
C13 0.0146(5) 0.0226(6) 0.0132(4) 0.0028(4) 0.0039(4) 0.0002(4)
C14 0.0156(5) 0.0177(5) 0.0167(5) -0.0001(4) 0.0082(4) 0.0014(4)
C15 0.0215(6) 0.0258(6) 0.0253(6) 0.0005(5) 0.0155(5) 0.0018(5)
C16 0.0205(5) 0.0159(5) 0.0208(5) -0.0011(4) 0.0088(4) -0.0011(4)
C17 0.0252(6) 0.0234(6) 0.0237(6) -0.0070(5) 0.0082(5) -0.0077(5)
C18 0.0174(6) 0.0348(7) 0.0129(5) 0.0022(5) 0.0027(4) -0.0033(5)
C19 0.0231(6) 0.0262(7) 0.0206(5) 0.0081(5) 0.0089(5) 0.0086(5)
C20 0.0212(6) 0.0261(6) 0.0193(5) -0.0002(4) 0.0095(5) 0.0048(5)
C21 0.0301(7) 0.0349(8) 0.0323(7) 0.0051(6) 0.0153(6) 0.0123(6)
C22 0.0292(7) 0.0327(8) 0.0214(6) -0.0061(5) 0.0105(5) 0.0030(6)
C23 0.0195(5) 0.0196(6) 0.0208(5) 0.0000(4) 0.0083(4) -0.0009(5)
C24 0.0308(7) 0.0268(7) 0.0276(6) -0.0059(5) 0.0140(6) -0.0060(6)
C25 0.0272(7) 0.0233(7) 0.0300(7) 0.0053(5) 0.0093(6) 0.0063(5)
C26 0.0237(6) 0.0232(6) 0.0156(5) -0.0025(4) 0.0073(4) 0.0054(5)
C27 0.0261(7) 0.0399(8) 0.0255(6) -0.0004(6) 0.0144(5) 0.0032(6)
C28 0.0335(7) 0.0224(6) 0.0232(6) 0.0002(5) 0.0106(5) 0.0080(6)
C29 0.0203(6) 0.0252(6) 0.0145(5) -0.0039(4) 0.0017(4) 0.0010(5)
C30 0.0289(8) 0.0331(9) 0.0477(10) -0.0112(7) 0.0036(7) -0.0069(7)
C31 0.0369(8) 0.0556(11) 0.0152(6) 0.0071(6) 0.0067(6) 0.0113(8)
C32 0.0203(5) 0.0173(5) 0.0128(4) -0.0025(4) 0.0042(4) 0.0008(4)
C33 0.0328(7) 0.0296(7) 0.0193(5) 0.0003(5) 0.0127(5) 0.0090(6)
C34 0.0282(7) 0.0182(6) 0.0254(6) -0.0010(5) 0.0047(5) -0.0022(5)
C35 0.0152(5) 0.0284(7) 0.0192(5) -0.0049(5) 0.0020(4) 0.0055(5)
C36 0.0184(6) 0.0470(9) 0.0266(7) -0.0089(6) 0.0076(5) -0.0062(6)
C37 0.0286(7) 0.0257(7) 0.0191(5) 0.0011(5) 0.0004(5) 0.0052(6)
C1S 0.083(2) 0.105(3) 0.169(5) -0.022(3) -0.005(3) -0.021(2)
C2S 0.0595(16) 0.079(2) 0.099(2) 0.0034(18) 0.0086(15) -0.0129(14)
C3S 0.067(2) 0.067(2) 0.066(2) 0.000 0.0083(17) 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
N1 C4 1.4262(15) . ?
N1 C7 1.4776(14) . ?
N1 C8 1.4248(15) . ?
N2 C3 1.3292(15) . ?
N2 C26 1.4810(16) . ?
N2 C29 1.4734(16) . ?
N3 C2 1.3329(15) . ?
N3 C32 1.4763(15) . ?
N3 C35 1.4774(16) . ?
B1 C1 1.5521(17) . ?
B1 C4 1.4692(16) . ?
B1 H1 1.107(19) . ?
C1 C2 1.3976(16) . ?
C1 C3 1.4053(16) . ?
C2 C3 1.3832(16) . ?
C4 C5 1.5371(15) . ?
C5 C6 1.5456(16) . ?
C5 C14 1.5332(16) . ?
C5 C16 1.5534(17) . ?
C6 C7 1.5370(17) . ?
C6 H6A 1.02(2) . ?
C6 H6B 0.98(2) . ?
C7 C18 1.5310(18) . ?
C7 C19 1.5391(19) . ?
C8 C9 1.4101(16) . ?
C8 C13 1.4122(18) . ?
C9 C10 1.3972(18) . ?
C9 C20 1.517(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.99(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.970(19) . ?
C12 C13 1.4006(17) . ?
C12 H12 0.99(2) . ?
C13 C23 1.5183(18) . ?
C14 C15 1.5308(17) . ?
C14 H14A 0.97(2) . ?
C14 H14B 0.99(2) . ?
C15 H15A 1.01(2) . ?
C15 H15B 1.009(19) . ?
C15 H15C 0.99(2) . ?
C16 C17 1.5232(19) . ?
C16 H16A 0.984(19) . ?
C16 H16B 1.02(2) . ?
C17 H17A 1.023(19) . ?
C17 H17B 0.97(2) . ?
C17 H17C 0.97(2) . ?
C18 H18A 0.966(19) . ?
C18 H18B 1.02(2) . ?
C18 H18C 1.01(2) . ?
C19 H19A 1.01(2) . ?
C19 H19B 0.96(2) . ?
C19 H19C 0.945(19) . ?
C20 C21 1.526(2) . ?
C20 C22 1.5389(19) . ?
C20 H20 0.985(19) . ?
C21 H21A 0.961(19) . ?
C21 H21B 1.00(2) . ?
C21 H21C 1.03(2) . ?
C22 H22A 0.97(2) . ?
C22 H22B 1.02(2) . ?
C22 H22C 1.007(19) . ?
C23 C24 1.5321(19) . ?
C23 C25 1.5328(19) . ?
C23 H23 0.95(2) . ?
C24 H24A 1.03(2) . ?
C24 H24B 1.096(19) . ?
C24 H24C 1.03(2) . ?
C25 H25A 0.96(2) . ?
C25 H25B 0.95(2) . ?
C25 H25C 0.95(2) . ?
C26 C27 1.518(2) . ?
C26 C28 1.525(2) . ?
C26 H26 1.02(2) . ?
C27 H27A 0.95(2) . ?
C27 H27B 0.95(2) . ?
C27 H27C 0.99(2) . ?
C28 H28A 0.99(2) . ?
C28 H28B 0.990(19) . ?
C28 H28C 1.002(19) . ?
C29 C30 1.520(2) . ?
C29 C31 1.520(2) . ?
C29 H29 0.97(2) . ?
C30 H30A 0.96(2) . ?
C30 H30B 0.96(2) . ?
C30 H30C 1.02(2) . ?
C31 H31A 1.00(2) . ?
C31 H31B 0.978(19) . ?
C31 H31C 0.92(2) . ?
C32 C33 1.5228(18) . ?
C32 C34 1.5204(19) . ?
C32 H32 0.989(19) . ?
C33 H33A 1.00(2) . ?
C33 H33B 0.96(2) . ?
C33 H33C 0.94(2) . ?
C34 H34A 0.97(2) . ?
C34 H34B 0.96(2) . ?
C34 H34C 0.97(2) . ?
C35 C36 1.520(2) . ?
C35 C37 1.526(2) . ?
C35 H35 1.03(2) . ?
C36 H36A 0.98(2) . ?
C36 H36B 0.94(2) . ?
C36 H36C 0.96(2) . ?
C37 H37A 0.97(2) . ?
C37 H37B 0.97(2) . ?
C37 H37C 0.97(2) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C1S C2S 1.579(7) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?
C2S C3S 1.507(4) . ?
C3S C2S 1.507(4) 2_655 ?
C3S H3S1 0.9900 . ?
C3S H3S2 0.9900 . ?
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
C4 N1 C7 115.23(9) . . ?
C8 N1 C4 121.09(9) . . ?
C8 N1 C7 122.54(9) . . ?
C3 N2 C26 119.30(10) . . ?
C3 N2 C29 121.89(10) . . ?
C29 N2 C26 118.76(10) . . ?
C2 N3 C32 116.99(9) . . ?
C2 N3 C35 122.25(10) . . ?
C32 N3 C35 119.01(10) . . ?
C1 B1 H1 110.9(10) . . ?
C4 B1 C1 128.50(10) . . ?
C4 B1 H1 120.6(10) . . ?
C2 C1 B1 153.10(11) . . ?
C2 C1 C3 59.14(8) . . ?
C3 C1 B1 146.70(11) . . ?
N3 C2 C1 144.81(11) . . ?
N3 C2 C3 154.32(11) . . ?
C3 C2 C1 60.71(8) . . ?
N2 C3 C1 147.33(11) . . ?
N2 C3 C2 152.51(11) . . ?
C2 C3 C1 60.15(8) . . ?
N1 C4 B1 121.35(10) . . ?
N1 C4 C5 105.85(9) . . ?
B1 C4 C5 132.22(10) . . ?
C4 C5 C6 103.16(9) . . ?
C4 C5 C16 111.05(9) . . ?
C6 C5 C16 109.51(9) . . ?
C14 C5 C4 113.09(9) . . ?
C14 C5 C6 109.54(9) . . ?
C14 C5 C16 110.23(9) . . ?
C5 C6 H6A 106.7(11) . . ?
C5 C6 H6B 111.2(12) . . ?
C7 C6 C5 107.12(9) . . ?
C7 C6 H6A 110.1(10) . . ?
C7 C6 H6B 114.9(11) . . ?
H6A C6 H6B 106.5(17) . . ?
N1 C7 C6 100.70(9) . . ?
N1 C7 C18 112.76(10) . . ?
N1 C7 C19 113.21(9) . . ?
C6 C7 C19 111.63(10) . . ?
C18 C7 C6 111.68(10) . . ?
C18 C7 C19 106.93(10) . . ?
C9 C8 N1 120.10(11) . . ?
C9 C8 C13 119.95(10) . . ?
C13 C8 N1 119.94(10) . . ?
C8 C9 C20 122.36(11) . . ?
C10 C9 C8 118.72(12) . . ?
C10 C9 C20 118.82(11) . . ?
C9 C10 H10 119.3(11) . . ?
C11 C10 C9 121.59(12) . . ?
C11 C10 H10 119.1(11) . . ?
C10 C11 C12 119.50(12) . . ?
C10 C11 H11 120.0(11) . . ?
C12 C11 H11 120.5(12) . . ?
C11 C12 C13 121.09(13) . . ?
C11 C12 H12 120.1(11) . . ?
C13 C12 H12 118.8(11) . . ?
C8 C13 C23 122.76(10) . . ?
C12 C13 C8 118.96(11) . . ?
C12 C13 C23 118.25(12) . . ?
C5 C14 H14A 108.3(11) . . ?
C5 C14 H14B 108.1(11) . . ?
C15 C14 C5 114.29(10) . . ?
C15 C14 H14A 109.9(11) . . ?
C15 C14 H14B 111.3(11) . . ?
H14A C14 H14B 104.5(17) . . ?
C14 C15 H15A 110.7(11) . . ?
C14 C15 H15B 111.1(11) . . ?
C14 C15 H15C 111.8(11) . . ?
H15A C15 H15B 105.0(15) . . ?
H15A C15 H15C 107.6(17) . . ?
H15B C15 H15C 110.3(16) . . ?
C5 C16 H16A 108.2(11) . . ?
C5 C16 H16B 110.6(11) . . ?
C17 C16 C5 116.38(11) . . ?
C17 C16 H16A 108.7(11) . . ?
C17 C16 H16B 108.4(10) . . ?
H16A C16 H16B 103.9(16) . . ?
C16 C17 H17A 110.6(11) . . ?
C16 C17 H17B 111.4(11) . . ?
C16 C17 H17C 109.3(11) . . ?
H17A C17 H17B 108.7(16) . . ?
H17A C17 H17C 111.0(16) . . ?
H17B C17 H17C 105.8(17) . . ?
C7 C18 H18A 109.6(12) . . ?
C7 C18 H18B 107.8(11) . . ?
C7 C18 H18C 111.8(11) . . ?
H18A C18 H18B 110.5(16) . . ?
H18A C18 H18C 106.8(16) . . ?
H18B C18 H18C 110.5(16) . . ?
C7 C19 H19A 112.2(11) . . ?
C7 C19 H19B 112.0(12) . . ?
C7 C19 H19C 110.2(12) . . ?
H19A C19 H19B 107.7(16) . . ?
H19A C19 H19C 107.8(16) . . ?
H19B C19 H19C 106.7(16) . . ?
C9 C20 C21 112.50(12) . . ?
C9 C20 C22 110.52(11) . . ?
C9 C20 H20 105.6(12) . . ?
C21 C20 C22 109.72(12) . . ?
C21 C20 H20 110.2(11) . . ?
C22 C20 H20 108.1(11) . . ?
C20 C21 H21A 109.2(12) . . ?
C20 C21 H21B 109.5(11) . . ?
C20 C21 H21C 111.4(11) . . ?
H21A C21 H21B 104.3(17) . . ?
H21A C21 H21C 109.4(16) . . ?
H21B C21 H21C 112.8(16) . . ?
C20 C22 H22A 114.1(12) . . ?
C20 C22 H22B 111.0(11) . . ?
C20 C22 H22C 113.3(11) . . ?
H22A C22 H22B 106.2(16) . . ?
H22A C22 H22C 105.6(16) . . ?
H22B C22 H22C 106.1(16) . . ?
C13 C23 C24 112.60(11) . . ?
C13 C23 C25 109.95(11) . . ?
C13 C23 H23 107.2(12) . . ?
C24 C23 C25 109.85(12) . . ?
C24 C23 H23 107.9(12) . . ?
C25 C23 H23 109.3(11) . . ?
C23 C24 H24A 113.3(11) . . ?
C23 C24 H24B 108.4(10) . . ?
C23 C24 H24C 111.8(11) . . ?
H24A C24 H24B 108.9(16) . . ?
H24A C24 H24C 106.1(15) . . ?
H24B C24 H24C 108.2(15) . . ?
C23 C25 H25A 110.0(12) . . ?
C23 C25 H25B 108.9(12) . . ?
C23 C25 H25C 109.8(12) . . ?
H25A C25 H25B 109.2(17) . . ?
H25A C25 H25C 110.2(18) . . ?
H25B C25 H25C 108.8(17) . . ?
N2 C26 C27 111.07(11) . . ?
N2 C26 C28 111.61(11) . . ?
N2 C26 H26 104.0(10) . . ?
C27 C26 C28 111.94(12) . . ?
C27 C26 H26 109.4(10) . . ?
C28 C26 H26 108.5(11) . . ?
C26 C27 H27A 112.5(11) . . ?
C26 C27 H27B 112.2(12) . . ?
C26 C27 H27C 110.7(11) . . ?
H27A C27 H27B 105.0(17) . . ?
H27A C27 H27C 109.0(17) . . ?
H27B C27 H27C 107.2(16) . . ?
C26 C28 H28A 109.9(11) . . ?
C26 C28 H28B 107.5(11) . . ?
C26 C28 H28C 109.8(11) . . ?
H28A C28 H28B 107.9(15) . . ?
H28A C28 H28C 114.2(16) . . ?
H28B C28 H28C 107.3(16) . . ?
N2 C29 C30 110.95(12) . . ?
N2 C29 C31 111.76(12) . . ?
N2 C29 H29 104.4(11) . . ?
C30 C29 H29 110.3(11) . . ?
C31 C29 C30 112.27(13) . . ?
C31 C29 H29 106.7(12) . . ?
C29 C30 H30A 110.7(11) . . ?
C29 C30 H30B 107.5(12) . . ?
C29 C30 H30C 110.6(11) . . ?
H30A C30 H30B 111.5(17) . . ?
H30A C30 H30C 107.2(17) . . ?
H30B C30 H30C 109.3(16) . . ?
C29 C31 H31A 109.8(11) . . ?
C29 C31 H31B 109.8(11) . . ?
C29 C31 H31C 110.8(13) . . ?
H31A C31 H31B 105.2(17) . . ?
H31A C31 H31C 108.0(17) . . ?
H31B C31 H31C 113.1(18) . . ?
N3 C32 C33 111.24(11) . . ?
N3 C32 C34 111.57(10) . . ?
N3 C32 H32 105.5(11) . . ?
C33 C32 H32 108.8(11) . . ?
C34 C32 C33 111.72(11) . . ?
C34 C32 H32 107.8(11) . . ?
C32 C33 H33A 112.0(11) . . ?
C32 C33 H33B 109.3(11) . . ?
C32 C33 H33C 109.8(12) . . ?
H33A C33 H33B 109.5(16) . . ?
H33A C33 H33C 111.7(17) . . ?
H33B C33 H33C 104.4(17) . . ?
C32 C34 H34A 111.7(12) . . ?
C32 C34 H34B 110.5(12) . . ?
C32 C34 H34C 109.5(11) . . ?
H34A C34 H34B 107.5(16) . . ?
H34A C34 H34C 109.5(17) . . ?
H34B C34 H34C 108.1(17) . . ?
N3 C35 C36 110.28(12) . . ?
N3 C35 C37 112.47(11) . . ?
N3 C35 H35 104.5(11) . . ?
C36 C35 C37 114.18(11) . . ?
C36 C35 H35 106.7(11) . . ?
C37 C35 H35 108.0(11) . . ?
C35 C36 H36A 112.2(11) . . ?
C35 C36 H36B 108.2(12) . . ?
C35 C36 H36C 111.6(12) . . ?
H36A C36 H36B 108.5(17) . . ?
H36A C36 H36C 108.7(17) . . ?
H36B C36 H36C 107.4(16) . . ?
C35 C37 H37A 110.8(12) . . ?
C35 C37 H37B 107.1(12) . . ?
C35 C37 H37C 110.1(12) . . ?
H37A C37 H37B 110.5(17) . . ?
H37A C37 H37C 107.5(16) . . ?
H37B C37 H37C 110.8(17) . . ?
H1S1 C1S H1S2 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C2S C1S H1S1 109.5 . . ?
C2S C1S H1S2 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
C1S C2S H2S1 108.2 . . ?
C1S C2S H2S2 108.2 . . ?
H2S1 C2S H2S2 107.4 . . ?
C3S C2S C1S 116.2(3) . . ?
C3S C2S H2S1 108.2 . . ?
C3S C2S H2S2 108.2 . . ?
C2S C3S C2S 117.5(4) 2_655 . ?
C2S C3S H3S1 107.9 2_655 . ?
C2S C3S H3S1 107.9 . . ?
C2S C3S H3S2 107.9 2_655 . ?
C2S C3S H3S2 107.9 . . ?
H3S1 C3S H3S2 107.2 . . ?
_database_code_depnum_ccdc_archive 'CCDC 1001683'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_gb_mm3_0m
_audit_creation_date 2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number 2013-2
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C35 H54 B N3'
_chemical_formula_sum 'C35 H54 B N3'
_chemical_formula_weight 527.62
_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'
N N 0.0061 0.0033 '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'
_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 16.2182(7)
_cell_length_b 9.3515(4)
_cell_length_c 21.6436(10)
_cell_angle_alpha 90
_cell_angle_beta 104.492(2)
_cell_angle_gamma 90
_cell_volume 3178.1(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6717
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 26.23
_cell_measurement_theta_min 2.54
_shelx_estimated_absorpt_T_max 0.7454
_shelx_estimated_absorpt_T_min 0.7220
_exptl_absorpt_coefficient_mu 0.063
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.7220
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0495 before and 0.0422 after correction.
The Ratio of minimum to maximum transmission is 0.9686.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.103
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description ?
_exptl_crystal_F_000 1160
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.16
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_unetI/netI 0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 22614
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.397
_diffrn_reflns_theta_min 1.413
_diffrn_ambient_temperature 100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4873
_reflns_number_total 6500
_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 ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.391
_refine_diff_density_min -0.579
_refine_diff_density_rms 0.169
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.111
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 359
_refine_ls_number_reflns 6500
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0786
_refine_ls_R_factor_gt 0.0492
_refine_ls_restrained_S_all 1.111
_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^)+(0.0937P)^2^+0.5412P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1318
_refine_ls_wR_factor_ref 0.1654
_refine_special_details
;
?
;
_olex2_refinement_description
;
1. Others
Fixed Uiso: H1A(0.035) H1B(0.035) H1C(0.035) H2(0.022) H9(0.03) H10(0.034)
H11(0.031) H12(0.025) H14(0.023) H15A(0.041) H15B(0.041) H15C(0.041)
H16A(0.04) H16B(0.04) H16C(0.04) H17(0.022) H18A(0.036) H18B(0.036)
H18C(0.036) H19A(0.042) H19B(0.042) H19C(0.042) H20A(0.043) H20B(0.043)
H22A(0.031) H22B(0.031) H23A(0.062) H23B(0.062) H23C(0.062) H24A(0.026)
H24B(0.026) H25A(0.047) H25B(0.047) H25C(0.047) H26A(0.045) H26B(0.045)
H26C(0.045) H27A(0.064) H27B(0.064) H27C(0.064) H28A(0.038) H28B(0.038)
H28C(0.038) H29(0.024) H30(0.025) H31(0.023) H33(0.023) H34A(0.038)
H34B(0.038) H34C(0.038) H35A(0.041) H35B(0.041) H35C(0.041) H1(0.017)
Fixed X: H1A(0.2812) H1B(0.2418) H1C(0.2253) H2(0.1049) H9(-0.0032)
H10(0.0704) H11(0.167) H12(0.1951) H14(0.1551) H15A(0.1727) H15B(0.1808)
H15C(0.092) H16A(0.2712) H16B(0.2973) H16C(0.2795) H17(-0.0397) H18A(0.0471)
H18B(0.0056) H18C(0.0852) H19A(-0.1356) H19B(-0.1443) H19C(-0.0956) H20A(-
0.1442) H20B(-0.1905) H22A(-0.2) H22B(-0.1215) H23A(-0.1388) H23B(-0.2165)
H23C(-0.2228) H24A(-0.0255) H24B(-0.0385) H25A(-0.178) H25B(-0.1167) H25C(-
0.1694) H26A(-0.1522) H26B(-0.1717) H26C(-0.0888) H27A(-0.0083) H27B(-0.0955)
H27C(-0.0202) H28A(0.1181) H28B(0.1753) H28C(0.2165) H29(0.2392) H30(0.2187)
H31(0.1043) H33(-0.0645) H34A(0.0394) H34B(-0.0361) H34C(0.0496) H35A(-0.0331)
H35B(-0.1188) H35C(-0.0903) H1(0.1038)
Fixed Y: H1A(0.561) H1B(0.6774) H1C(0.5148) H2(0.6234) H9(0.1817) H10(0.2627)
H11(0.447) H12(0.5563) H14(0.5883) H15A(0.7281) H15B(0.8) H15C(0.7454)
H16A(0.4484) H16B(0.6102) H16C(0.5324) H17(0.1822) H18A(0.0196) H18B(-0.0425)
H18C(0.0581) H19A(0.2364) H19B(0.0834) H19C(0.1042) H20A(0.6616) H20B(0.5126)
H22A(0.4964) H22B(0.4153) H23A(0.2388) H23B(0.2458) H23C(0.3163) H24A(0.7114)
H24B(0.6363) H25A(0.7206) H25B(0.8506) H25C(0.7885) H26A(0.3345) H26B(0.4659)
H26C(0.3754) H27A(0.6022) H27B(0.6803) H27C(0.7039) H28A(0.7043) H28B(0.7945)
H28C(0.6761) H29(0.4255) H30(0.1949) H31(0.0639) H33(0.1911) H34A(0.0743)
H34B(-0.03) H34C(-0.0425) H35A(-0.0211) H35B(-0.0023) H35C(0.1135) H1(0.3462)
Fixed Z: H1A(0.4019) H1B(0.3508) H1C(0.3348) H2(0.3591) H9(-0.0005) H10(-
0.0726) H11(-0.047) H12(0.0525) H14(0.2269) H15A(0.1156) H15B(0.1823)
H15C(0.1425) H16A(0.2204) H16B(0.2257) H16C(0.1595) H17(0.1759) H18A(0.1024)
H18B(0.1548) H18C(0.1744) H19A(0.0732) H19B(0.1005) H19C(0.047) H20A(0.2934)
H20B(0.2848) H22A(0.1649) H22B(0.1522) H23A(0.2273) H23B(0.1674) H23C(0.2317)
H24A(0.2428) H24B(0.1765) H25A(0.1452) H25B(0.1673) H25C(0.2127) H26A(0.3641)
H26B(0.4032) H26C(0.4291) H27A(0.4386) H27B(0.4118) H27C(0.3794) H28A(0.4651)
H28B(0.4311) H28C(0.4805) H29(0.4857) H30(0.5158) H31(0.4587) H33(0.3321)
H34A(0.2917) H34B(0.2922) H34C(0.345) H35A(0.4285) H35B(0.3762) H35C(0.4297)
H1(0.2728)
;
_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
N1 N 0.02193(9) 0.29746(16) 0.12354(7) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.11533(9) 0.46986(15) 0.14838(6) 0.0149(3) Uani 1 1 d . . . . .
C3 C -0.07913(11) 0.50984(19) 0.35617(8) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.23277(12) 0.5855(2) 0.36787(9) 0.0235(4) Uani 1 1 d . . . . .
H1A H 0.2812 0.5610 0.4019 0.035 Uiso 1 1 calc GR . . . .
H1B H 0.2418 0.6774 0.3508 0.035 Uiso 1 1 calc GR . . . .
H1C H 0.2253 0.5148 0.3348 0.035 Uiso 1 1 calc GR . . . .
C2 C 0.15267(11) 0.59116(19) 0.39365(8) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.1049 0.6234 0.3591 0.022 Uiso 1 1 calc R . . . .
C4 C 0.13192(11) 0.44241(19) 0.41422(8) 0.0158(4) Uani 1 1 d . . . . .
C5 C 0.05774(11) 0.36644(18) 0.38329(7) 0.0139(4) Uani 1 1 d . . . . .
N5 N -0.00867(9) 0.43520(15) 0.33689(6) 0.0140(3) Uiso 1 1 d . . . . .
C6 C -0.01154(11) 0.43796(18) 0.27089(8) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.06090(10) 0.38739(18) 0.17213(8) 0.0134(4) Uani 1 1 d . . . . .
C8 C 0.05273(11) 0.32103(19) 0.06991(8) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.03613(13) 0.2557(2) 0.01022(9) 0.0252(4) Uani 1 1 d . . . . .
H9 H -0.0032 0.1817 -0.0005 0.030 Uiso 1 1 calc R . . . .
C10 C 0.08012(14) 0.3049(2) -0.03253(9) 0.0285(5) Uani 1 1 d . . . . .
H10 H 0.0704 0.2627 -0.0726 0.034 Uiso 1 1 calc R . . . .
C11 C 0.13880(13) 0.4162(2) -0.01699(9) 0.0258(4) Uani 1 1 d . . . . .
H11 H 0.1670 0.4470 -0.0470 0.031 Uiso 1 1 calc R . . . .
C12 C 0.15603(12) 0.4819(2) 0.04213(8) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.1951 0.5563 0.0525 0.025 Uiso 1 1 calc R . . . .
C13 C 0.11211(11) 0.43166(19) 0.08547(8) 0.0154(4) Uani 1 1 d . . . . .
C14 C 0.16965(11) 0.58147(19) 0.18566(8) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.1551 0.5883 0.2269 0.023 Uiso 1 1 calc R . . . .
C15 C 0.15217(14) 0.7272(2) 0.15351(10) 0.0276(5) Uani 1 1 d . . . . .
H15A H 0.1727 0.7281 0.1156 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.1808 0.8000 0.1823 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.0920 0.7454 0.1425 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.26302(12) 0.5392(2) 0.19904(9) 0.0265(4) Uani 1 1 d . . . . .
H16A H 0.2712 0.4484 0.2204 0.040 Uiso 1 1 calc GR . . . .
H16B H 0.2973 0.6102 0.2257 0.040 Uiso 1 1 calc GR . . . .
H16C H 0.2795 0.5324 0.1595 0.040 Uiso 1 1 calc GR . . . .
C17 C -0.02489(11) 0.16851(19) 0.13505(9) 0.0183(4) Uani 1 1 d . . . . .
H17 H -0.0397 0.1822 0.1759 0.022 Uiso 1 1 calc R . . . .
C18 C 0.03366(12) 0.0390(2) 0.14233(9) 0.0240(4) Uani 1 1 d . . . . .
H18A H 0.0471 0.0196 0.1024 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.0056 -0.0425 0.1548 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.0852 0.0581 0.1744 0.036 Uiso 1 1 calc GR . . . .
C19 C -0.10776(12) 0.1460(2) 0.08423(10) 0.0283(5) Uani 1 1 d . . . . .
H19A H -0.1356 0.2364 0.0732 0.042 Uiso 1 1 calc GR . . . .
H19B H -0.1443 0.0834 0.1005 0.042 Uiso 1 1 calc GR . . . .
H19C H -0.0956 0.1042 0.0470 0.042 Uiso 1 1 calc GR . . . .
C20 C -0.13544(14) 0.5592(3) 0.29248(9) 0.0361(6) Uani 1 1 d . . . . .
H20A H -0.1442 0.6616 0.2934 0.043 Uiso 1 1 calc R . . . .
H20B H -0.1905 0.5126 0.2848 0.043 Uiso 1 1 calc R . . . .
C21 C -0.09235(11) 0.5214(2) 0.23824(8) 0.0192(4) Uani 1 1 d . . . . .
C22 C -0.15184(12) 0.4362(2) 0.18449(9) 0.0262(5) Uani 1 1 d . . . . .
H22A H -0.2000 0.4964 0.1649 0.031 Uiso 1 1 calc R . . . .
H22B H -0.1215 0.4153 0.1522 0.031 Uiso 1 1 calc R . . . .
C23 C -0.18560(14) 0.2964(3) 0.20458(12) 0.0412(6) Uani 1 1 d . . . . .
H23A H -0.1388 0.2388 0.2273 0.062 Uiso 1 1 calc GR . . . .
H23B H -0.2165 0.2458 0.1674 0.062 Uiso 1 1 calc GR . . . .
H23C H -0.2228 0.3163 0.2317 0.062 Uiso 1 1 calc GR . . . .
C24 C -0.06668(12) 0.6615(2) 0.20954(9) 0.0216(4) Uani 1 1 d . . . . .
H24A H -0.0255 0.7114 0.2428 0.026 Uiso 1 1 calc R . . . .
H24B H -0.0385 0.6363 0.1765 0.026 Uiso 1 1 calc R . . . .
C25 C -0.13950(14) 0.7649(2) 0.18100(10) 0.0311(5) Uani 1 1 d . . . . .
H25A H -0.1780 0.7206 0.1452 0.047 Uiso 1 1 calc GR . . . .
H25B H -0.1167 0.8506 0.1673 0.047 Uiso 1 1 calc GR . . . .
H25C H -0.1694 0.7885 0.2127 0.047 Uiso 1 1 calc GR . . . .
C26 C -0.12742(13) 0.4124(2) 0.39143(10) 0.0298(5) Uani 1 1 d . . . . .
H26A H -0.1522 0.3345 0.3641 0.045 Uiso 1 1 calc GR . . . .
H26B H -0.1717 0.4659 0.4032 0.045 Uiso 1 1 calc GR . . . .
H26C H -0.0888 0.3754 0.4291 0.045 Uiso 1 1 calc GR . . . .
C27 C -0.04792(14) 0.6357(3) 0.40060(13) 0.0426(6) Uani 1 1 d . . . . .
H27A H -0.0083 0.6022 0.4386 0.064 Uiso 1 1 calc GR . . . .
H27B H -0.0955 0.6803 0.4118 0.064 Uiso 1 1 calc GR . . . .
H27C H -0.0202 0.7039 0.3794 0.064 Uiso 1 1 calc GR . . . .
C28 C 0.16699(13) 0.7019(2) 0.44764(9) 0.0255(4) Uani 1 1 d . . . . .
H28A H 0.1181 0.7043 0.4651 0.038 Uiso 1 1 calc GR . . . .
H28B H 0.1753 0.7945 0.4311 0.038 Uiso 1 1 calc GR . . . .
H28C H 0.2165 0.6761 0.4805 0.038 Uiso 1 1 calc GR . . . .
C29 C 0.19116(11) 0.3753(2) 0.46397(8) 0.0200(4) Uani 1 1 d . . . . .
H29 H 0.2392 0.4255 0.4857 0.024 Uiso 1 1 calc R . . . .
C30 C 0.17979(12) 0.2364(2) 0.48151(8) 0.0210(4) Uani 1 1 d . . . . .
H30 H 0.2187 0.1949 0.5158 0.025 Uiso 1 1 calc R . . . .
C31 C 0.11027(12) 0.1590(2) 0.44796(8) 0.0196(4) Uani 1 1 d . . . . .
H31 H 0.1043 0.0639 0.4587 0.023 Uiso 1 1 calc R . . . .
C32 C 0.04878(11) 0.22102(19) 0.39820(8) 0.0162(4) Uani 1 1 d . . . . .
C33 C -0.02337(12) 0.12816(19) 0.36033(8) 0.0193(4) Uani 1 1 d . . . . .
H33 H -0.0645 0.1911 0.3321 0.023 Uiso 1 1 calc R . . . .
C34 C 0.01053(13) 0.0226(2) 0.31836(9) 0.0254(4) Uani 1 1 d . . . . .
H34A H 0.0394 0.0743 0.2917 0.038 Uiso 1 1 calc GR . . . .
H34B H -0.0361 -0.0300 0.2922 0.038 Uiso 1 1 calc GR . . . .
H34C H 0.0496 -0.0425 0.3450 0.038 Uiso 1 1 calc GR . . . .
C35 C -0.07084(13) 0.0469(2) 0.40264(10) 0.0274(5) Uani 1 1 d . . . . .
H35A H -0.0331 -0.0211 0.4285 0.041 Uiso 1 1 calc GR . . . .
H35B H -0.1188 -0.0023 0.3762 0.041 Uiso 1 1 calc GR . . . .
H35C H -0.0903 0.1135 0.4297 0.041 Uiso 1 1 calc GR . . . .
B1 B 0.05694(12) 0.3855(2) 0.24395(9) 0.0142(4) Uani 1 1 d . . . . .
H1 H 0.1038 0.3462 0.2728 0.017 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
N1 0.0151(7) 0.0185(8) 0.0132(7) 0.0000(6) 0.0019(6) -0.0032(6)
N2 0.0177(7) 0.0155(7) 0.0125(7) -0.0003(6) 0.0056(6) -0.0013(6)
C3 0.0155(9) 0.0175(9) 0.0186(9) 0.0023(7) 0.0075(7) 0.0035(7)
C1 0.0206(9) 0.0276(11) 0.0232(10) 0.0009(8) 0.0070(8) -0.0059(8)
C2 0.0180(9) 0.0190(9) 0.0174(9) 0.0001(7) 0.0045(7) -0.0021(7)
C4 0.0182(9) 0.0164(9) 0.0144(8) -0.0014(7) 0.0070(7) 0.0026(7)
C5 0.0163(8) 0.0165(9) 0.0102(8) 0.0005(7) 0.0060(7) 0.0025(7)
C6 0.0143(8) 0.0155(9) 0.0141(8) 0.0034(7) 0.0038(7) -0.0009(7)
C7 0.0113(8) 0.0127(8) 0.0156(8) 0.0017(7) 0.0024(6) 0.0021(7)
C8 0.0183(9) 0.0196(9) 0.0136(8) 0.0015(7) 0.0029(7) 0.0020(7)
C9 0.0275(10) 0.0296(11) 0.0166(9) -0.0043(8) 0.0019(8) -0.0041(9)
C10 0.0369(12) 0.0366(12) 0.0115(9) -0.0034(8) 0.0051(8) 0.0025(10)
C11 0.0321(11) 0.0325(11) 0.0152(9) 0.0067(8) 0.0101(8) 0.0064(9)
C12 0.0237(10) 0.0213(10) 0.0185(9) 0.0042(7) 0.0085(8) 0.0009(8)
C13 0.0175(9) 0.0174(9) 0.0115(8) 0.0017(7) 0.0037(7) 0.0035(7)
C14 0.0225(9) 0.0186(9) 0.0162(9) -0.0031(7) 0.0062(7) -0.0059(7)
C15 0.0349(12) 0.0175(10) 0.0306(11) -0.0023(8) 0.0086(9) -0.0049(9)
C16 0.0219(10) 0.0312(11) 0.0244(10) 0.0001(9) 0.0022(8) -0.0065(9)
C17 0.0151(9) 0.0182(9) 0.0198(9) 0.0013(7) 0.0013(7) -0.0048(7)
C18 0.0243(10) 0.0195(10) 0.0262(10) -0.0010(8) 0.0028(8) -0.0024(8)
C19 0.0214(10) 0.0285(11) 0.0301(11) 0.0024(9) -0.0028(8) -0.0072(8)
C20 0.0294(11) 0.0593(16) 0.0245(11) 0.0155(10) 0.0159(9) 0.0229(11)
C21 0.0158(9) 0.0260(10) 0.0172(9) 0.0074(8) 0.0067(7) 0.0075(8)
C22 0.0130(9) 0.0361(12) 0.0276(10) 0.0073(9) 0.0016(8) 0.0031(8)
C23 0.0240(11) 0.0496(15) 0.0533(15) 0.0052(12) 0.0160(10) -0.0104(10)
C24 0.0240(10) 0.0217(10) 0.0203(9) 0.0051(8) 0.0079(8) 0.0077(8)
C25 0.0327(11) 0.0300(12) 0.0325(11) 0.0099(9) 0.0116(9) 0.0141(9)
C26 0.0285(11) 0.0346(12) 0.0333(11) 0.0131(9) 0.0210(9) 0.0110(9)
C27 0.0291(12) 0.0337(13) 0.0711(17) -0.0265(12) 0.0240(12) -0.0012(10)
C28 0.0296(11) 0.0223(10) 0.0250(10) -0.0030(8) 0.0076(8) -0.0053(8)
C29 0.0169(9) 0.0264(10) 0.0159(9) -0.0027(7) 0.0025(7) 0.0008(8)
C30 0.0220(10) 0.0275(10) 0.0128(9) 0.0033(7) 0.0030(7) 0.0079(8)
C31 0.0267(10) 0.0163(9) 0.0171(9) 0.0034(7) 0.0082(8) 0.0044(8)
C32 0.0201(9) 0.0163(9) 0.0141(8) 0.0001(7) 0.0081(7) 0.0020(7)
C33 0.0222(9) 0.0157(9) 0.0195(9) 0.0017(7) 0.0048(7) -0.0002(7)
C34 0.0320(11) 0.0211(10) 0.0227(10) -0.0025(8) 0.0058(8) -0.0006(9)
C35 0.0325(11) 0.0210(10) 0.0310(11) 0.0018(8) 0.0121(9) -0.0056(9)
B1 0.0129(9) 0.0150(10) 0.0133(9) 0.0024(7) 0.0006(7) 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
N1 C7 1.371(2) . ?
N1 C8 1.391(2) . ?
N1 C17 1.479(2) . ?
N2 C7 1.366(2) . ?
N2 C13 1.396(2) . ?
N2 C14 1.470(2) . ?
C3 N5 1.485(2) . ?
C3 C20 1.522(3) . ?
C3 C26 1.525(2) . ?
C3 C27 1.524(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.538(2) . ?
C2 H2 0.9800 . ?
C2 C4 1.524(2) . ?
C2 C28 1.535(3) . ?
C4 C5 1.413(2) . ?
C4 C29 1.399(2) . ?
C5 N5 1.428(2) . ?
C5 C32 1.413(2) . ?
N5 C6 1.418(2) . ?
C6 C21 1.537(2) . ?
C6 B1 1.462(3) . ?
C7 B1 1.572(2) . ?
C8 C9 1.393(3) . ?
C8 C13 1.396(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(2) . ?
C14 H14 0.9800 . ?
C14 C15 1.524(3) . ?
C14 C16 1.521(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.523(3) . ?
C17 C19 1.523(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.550(3) . ?
C21 C22 1.535(3) . ?
C21 C24 1.551(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.523(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.532(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.379(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.383(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.398(2) . ?
C32 C33 1.522(2) . ?
C33 H33 0.9800 . ?
C33 C34 1.533(3) . ?
C33 C35 1.536(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
B1 H1 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 110.48(14) . . ?
C7 N1 C17 121.90(14) . . ?
C8 N1 C17 125.19(15) . . ?
C7 N2 C13 110.66(14) . . ?
C7 N2 C14 123.32(14) . . ?
C13 N2 C14 126.01(14) . . ?
N5 C3 C20 102.56(14) . . ?
N5 C3 C26 112.79(15) . . ?
N5 C3 C27 112.50(15) . . ?
C20 C3 C26 111.56(16) . . ?
C20 C3 C27 111.51(18) . . ?
C27 C3 C26 106.08(16) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 108.2 . . ?
C4 C2 C1 110.07(15) . . ?
C4 C2 H2 108.2 . . ?
C4 C2 C28 113.32(15) . . ?
C28 C2 C1 108.59(15) . . ?
C28 C2 H2 108.2 . . ?
C5 C4 C2 123.00(15) . . ?
C29 C4 C2 118.35(16) . . ?
C29 C4 C5 118.58(16) . . ?
C4 C5 N5 120.63(15) . . ?
C4 C5 C32 119.96(15) . . ?
C32 C5 N5 119.41(15) . . ?
C5 N5 C3 120.78(13) . . ?
C6 N5 C3 116.16(13) . . ?
C6 N5 C5 123.05(14) . . ?
N5 C6 C21 106.36(14) . . ?
N5 C6 B1 123.98(15) . . ?
B1 C6 C21 129.23(15) . . ?
N1 C7 B1 128.78(15) . . ?
N2 C7 N1 105.96(14) . . ?
N2 C7 B1 124.68(15) . . ?
N1 C8 C9 132.69(17) . . ?
N1 C8 C13 106.63(15) . . ?
C9 C8 C13 120.67(17) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 C8 117.59(18) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.54(18) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.51(18) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.98(18) . . ?
C13 C12 H12 121.5 . . ?
N2 C13 C8 106.26(15) . . ?
C12 C13 N2 132.03(17) . . ?
C12 C13 C8 121.70(16) . . ?
N2 C14 H14 107.3 . . ?
N2 C14 C15 111.52(15) . . ?
N2 C14 C16 110.58(15) . . ?
C15 C14 H14 107.3 . . ?
C16 C14 H14 107.3 . . ?
C16 C14 C15 112.45(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17 107.3 . . ?
N1 C17 C18 109.45(14) . . ?
N1 C17 C19 112.84(15) . . ?
C18 C17 H17 107.3 . . ?
C18 C17 C19 112.31(16) . . ?
C19 C17 H17 107.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.8 . . ?
C3 C20 H20B 109.8 . . ?
C3 C20 C21 109.57(15) . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C6 C21 C20 105.17(14) . . ?
C6 C21 C24 109.24(14) . . ?
C20 C21 C24 109.15(17) . . ?
C22 C21 C6 112.76(15) . . ?
C22 C21 C20 112.04(16) . . ?
C22 C21 C24 108.40(14) . . ?
C21 C22 H22A 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 C21 115.59(17) . . ?
C23 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 108.3 . . ?
C21 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C25 C24 C21 115.96(16) . . ?
C25 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C26 H26A 109.5 . . ?
C3 C26 H26B 109.5 . . ?
C3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C27 H27A 109.5 . . ?
C3 C27 H27B 109.5 . . ?
C3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C29 H29 119.3 . . ?
C30 C29 C4 121.39(17) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.75(17) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.4 . . ?
C30 C31 C32 121.19(17) . . ?
C32 C31 H31 119.4 . . ?
C5 C32 C33 122.36(15) . . ?
C31 C32 C5 118.76(16) . . ?
C31 C32 C33 118.84(16) . . ?
C32 C33 H33 107.8 . . ?
C32 C33 C34 110.18(15) . . ?
C32 C33 C35 113.19(15) . . ?
C34 C33 H33 107.8 . . ?
C34 C33 C35 110.02(16) . . ?
C35 C33 H33 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C6 B1 C7 127.84(15) . . ?
C6 B1 H1 116.1 . . ?
C7 B1 H1 116.1 . . ?
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
N1 C7 B1 C6 -78.5(3) . . . . ?
N1 C8 C9 C10 -178.69(19) . . . . ?
N1 C8 C13 N2 0.48(19) . . . . ?
N1 C8 C13 C12 179.55(16) . . . . ?
N2 C7 B1 C6 111.5(2) . . . . ?
C3 N5 C6 C21 -0.59(19) . . . . ?
C3 N5 C6 B1 172.48(16) . . . . ?
C3 C20 C21 C6 4.1(2) . . . . ?
C3 C20 C21 C22 126.89(18) . . . . ?
C3 C20 C21 C24 -113.04(19) . . . . ?
C1 C2 C4 C5 -114.00(18) . . . . ?
C1 C2 C4 C29 62.7(2) . . . . ?
C2 C4 C5 N5 -9.8(2) . . . . ?
C2 C4 C5 C32 170.16(15) . . . . ?
C2 C4 C29 C30 -174.62(16) . . . . ?
C4 C5 N5 C3 -89.51(19) . . . . ?
C4 C5 N5 C6 90.0(2) . . . . ?
C4 C5 C32 C31 6.1(2) . . . . ?
C4 C5 C32 C33 -171.38(15) . . . . ?
C4 C29 C30 C31 2.5(3) . . . . ?
C5 C4 C29 C30 2.3(3) . . . . ?
C5 N5 C6 C21 179.90(15) . . . . ?
C5 N5 C6 B1 -7.0(3) . . . . ?
C5 C32 C33 C34 106.62(19) . . . . ?
C5 C32 C33 C35 -129.73(18) . . . . ?
N5 C3 C20 C21 -4.2(2) . . . . ?
N5 C5 C32 C31 -173.90(15) . . . . ?
N5 C5 C32 C33 8.6(2) . . . . ?
N5 C6 C21 C20 -2.1(2) . . . . ?
N5 C6 C21 C22 -124.49(15) . . . . ?
N5 C6 C21 C24 114.92(15) . . . . ?
N5 C6 B1 C7 -178.28(16) . . . . ?
C6 C21 C22 C23 60.6(2) . . . . ?
C6 C21 C24 C25 -174.06(16) . . . . ?
C7 N1 C8 C9 177.54(19) . . . . ?
C7 N1 C8 C13 -1.03(19) . . . . ?
C7 N1 C17 C18 -95.50(19) . . . . ?
C7 N1 C17 C19 138.66(17) . . . . ?
C7 N2 C13 C8 0.23(19) . . . . ?
C7 N2 C13 C12 -178.70(18) . . . . ?
C7 N2 C14 C15 -121.95(18) . . . . ?
C7 N2 C14 C16 112.15(18) . . . . ?
C8 N1 C7 N2 1.16(19) . . . . ?
C8 N1 C7 B1 -170.29(16) . . . . ?
C8 N1 C17 C18 65.1(2) . . . . ?
C8 N1 C17 C19 -60.7(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C8 C13 N2 -178.30(16) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 N2 178.15(18) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C13 N2 C7 N1 -0.85(18) . . . . ?
C13 N2 C7 B1 171.05(15) . . . . ?
C13 N2 C14 C15 58.8(2) . . . . ?
C13 N2 C14 C16 -67.1(2) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C14 N2 C7 N1 179.82(15) . . . . ?
C14 N2 C7 B1 -8.3(3) . . . . ?
C14 N2 C13 C8 179.54(15) . . . . ?
C14 N2 C13 C12 0.6(3) . . . . ?
C17 N1 C7 N2 164.33(14) . . . . ?
C17 N1 C7 B1 -7.1(3) . . . . ?
C17 N1 C8 C9 15.0(3) . . . . ?
C17 N1 C8 C13 -163.53(15) . . . . ?
C20 C3 N5 C5 -177.43(16) . . . . ?
C20 C3 N5 C6 3.1(2) . . . . ?
C20 C21 C22 C23 -57.8(2) . . . . ?
C20 C21 C24 C25 -59.6(2) . . . . ?
C21 C6 B1 C7 -6.9(3) . . . . ?
C22 C21 C24 C25 62.7(2) . . . . ?
C24 C21 C22 C23 -178.34(17) . . . . ?
C26 C3 N5 C5 -57.3(2) . . . . ?
C26 C3 N5 C6 123.18(16) . . . . ?
C26 C3 C20 C21 -125.21(19) . . . . ?
C27 C3 N5 C5 62.6(2) . . . . ?
C27 C3 N5 C6 -116.87(18) . . . . ?
C27 C3 C20 C21 116.38(19) . . . . ?
C28 C2 C4 C5 124.19(18) . . . . ?
C28 C2 C4 C29 -59.1(2) . . . . ?
C29 C4 C5 N5 173.44(15) . . . . ?
C29 C4 C5 C32 -6.6(2) . . . . ?
C29 C30 C31 C32 -3.0(3) . . . . ?
C30 C31 C32 C5 -1.3(3) . . . . ?
C30 C31 C32 C33 176.28(16) . . . . ?
C31 C32 C33 C34 -70.9(2) . . . . ?
C31 C32 C33 C35 52.8(2) . . . . ?
C32 C5 N5 C3 90.49(19) . . . . ?
C32 C5 N5 C6 -90.0(2) . . . . ?
B1 C6 C21 C20 -174.70(19) . . . . ?
B1 C6 C21 C22 62.9(2) . . . . ?
B1 C6 C21 C24 -57.7(2) . . . . ?
_shelx_res_file
;
TITL GB_MM3_0m in P2(1)/n
CELL 0.71073 16.2182 9.3515 21.6436 90 104.492 90
ZERR 4 0.0007 0.0004 0.001 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N B
UNIT 140 216 12 4
L.S. 10
PLAN -5 0 0
TEMP 0
HTAB
BOND $H
CONF
fmap 2
acta
REM /Users/david_ruiz06/Desktop/DAR/Structures%20aux%20rayons%20X/CAAC(Di
REM ppEt2)_BH_BMI_borylene/GB_MM3_0m.hkl
WGHT 0.093700 0.541200
FVAR 0.55990
N1 3 0.021926 0.297464 0.123544 11.00000 0.01509 0.01846 =
0.01323 0.00004 0.00193 -0.00319
N2 3 0.115325 0.469857 0.148379 11.00000 0.01770 0.01550 =
0.01253 -0.00031 0.00562 -0.00134
C3 1 -0.079135 0.509836 0.356170 11.00000 0.01548 0.01747 =
0.01865 0.00231 0.00753 0.00350
C1 1 0.232765 0.585546 0.367866 11.00000 0.02059 0.02764 =
0.02317 0.00085 0.00703 -0.00588
AFIX 137
H1A 2 0.281189 0.561011 0.401862 11.00000 -1.50000
H1B 2 0.241840 0.677350 0.350841 11.00000 -1.50000
H1C 2 0.225271 0.514771 0.334795 11.00000 -1.50000
AFIX 0
C2 1 0.152668 0.591164 0.393653 11.00000 0.01798 0.01903 =
0.01740 0.00006 0.00446 -0.00214
AFIX 13
H2 2 0.104850 0.623395 0.359136 11.00000 -1.20000
AFIX 0
C4 1 0.131924 0.442405 0.414221 11.00000 0.01819 0.01644 =
0.01436 -0.00141 0.00697 0.00257
C5 1 0.057736 0.366442 0.383289 11.00000 0.01633 0.01652 =
0.01021 0.00053 0.00604 0.00249
N5 3 -0.008666 0.435196 0.336891 11.00000 0.01402
C6 1 -0.011537 0.437957 0.270886 11.00000 0.01429 0.01546 =
0.01411 0.00340 0.00383 -0.00094
C7 1 0.060900 0.387386 0.172133 11.00000 0.01133 0.01273 =
0.01555 0.00169 0.00239 0.00205
C8 1 0.052725 0.321028 0.069910 11.00000 0.01826 0.01959 =
0.01358 0.00151 0.00285 0.00199
C9 1 0.036130 0.255721 0.010217 11.00000 0.02753 0.02956 =
0.01656 -0.00425 0.00188 -0.00414
AFIX 43
H9 2 -0.003156 0.181694 -0.000458 11.00000 -1.20000
AFIX 0
C10 1 0.080122 0.304879 -0.032527 11.00000 0.03686 0.03659 =
0.01154 -0.00345 0.00507 0.00253
AFIX 43
H10 2 0.070368 0.262714 -0.072623 11.00000 -1.20000
AFIX 0
C11 1 0.138800 0.416205 -0.016989 11.00000 0.03209 0.03248 =
0.01520 0.00668 0.01014 0.00640
AFIX 43
H11 2 0.167022 0.447024 -0.047049 11.00000 -1.20000
AFIX 0
C12 1 0.156027 0.481918 0.042131 11.00000 0.02366 0.02128 =
0.01846 0.00418 0.00850 0.00092
AFIX 43
H12 2 0.195141 0.556268 0.052485 11.00000 -1.20000
AFIX 0
C13 1 0.112114 0.431657 0.085468 11.00000 0.01746 0.01739 =
0.01146 0.00172 0.00365 0.00346
C14 1 0.169650 0.581474 0.185658 11.00000 0.02252 0.01856 =
0.01616 -0.00305 0.00623 -0.00590
AFIX 13
H14 2 0.155129 0.588259 0.226874 11.00000 -1.20000
AFIX 0
C15 1 0.152167 0.727211 0.153509 11.00000 0.03492 0.01754 =
0.03064 -0.00230 0.00858 -0.00486
AFIX 137
H15A 2 0.172656 0.728068 0.115563 11.00000 -1.50000
H15B 2 0.180837 0.799979 0.182256 11.00000 -1.50000
H15C 2 0.091994 0.745377 0.142460 11.00000 -1.50000
AFIX 0
C16 1 0.263016 0.539224 0.199041 11.00000 0.02190 0.03119 =
0.02437 0.00014 0.00220 -0.00646
AFIX 137
H16A 2 0.271237 0.448374 0.220355 11.00000 -1.50000
H16B 2 0.297253 0.610218 0.225697 11.00000 -1.50000
H16C 2 0.279489 0.532412 0.159517 11.00000 -1.50000
AFIX 0
C17 1 -0.024894 0.168510 0.135054 11.00000 0.01510 0.01822 =
0.01985 0.00125 0.00134 -0.00478
AFIX 13
H17 2 -0.039717 0.182165 0.175860 11.00000 -1.20000
AFIX 0
C18 1 0.033658 0.038952 0.142334 11.00000 0.02434 0.01949 =
0.02624 -0.00097 0.00276 -0.00239
AFIX 137
H18A 2 0.047146 0.019615 0.102416 11.00000 -1.50000
H18B 2 0.005582 -0.042541 0.154754 11.00000 -1.50000
H18C 2 0.085151 0.058117 0.174422 11.00000 -1.50000
AFIX 0
C19 1 -0.107763 0.146041 0.084233 11.00000 0.02136 0.02849 =
0.03009 0.00241 -0.00284 -0.00717
AFIX 137
H19A 2 -0.135632 0.236425 0.073220 11.00000 -1.50000
H19B 2 -0.144263 0.083362 0.100470 11.00000 -1.50000
H19C 2 -0.095620 0.104174 0.046981 11.00000 -1.50000
AFIX 0
C20 1 -0.135440 0.559152 0.292482 11.00000 0.02938 0.05931 =
0.02449 0.01548 0.01588 0.02294
AFIX 23
H20A 2 -0.144239 0.661642 0.293448 11.00000 -1.20000
H20B 2 -0.190535 0.512630 0.284769 11.00000 -1.20000
AFIX 0
C21 1 -0.092354 0.521406 0.238238 11.00000 0.01579 0.02600 =
0.01716 0.00737 0.00674 0.00753
C22 1 -0.151843 0.436235 0.184491 11.00000 0.01298 0.03609 =
0.02756 0.00726 0.00164 0.00315
AFIX 23
H22A 2 -0.200013 0.496384 0.164882 11.00000 -1.20000
H22B 2 -0.121534 0.415263 0.152188 11.00000 -1.20000
AFIX 0
C23 1 -0.185596 0.296354 0.204579 11.00000 0.02396 0.04961 =
0.05333 0.00522 0.01600 -0.01044
AFIX 137
H23A 2 -0.138774 0.238778 0.227310 11.00000 -1.50000
H23B 2 -0.216491 0.245753 0.167370 11.00000 -1.50000
H23C 2 -0.222801 0.316347 0.231722 11.00000 -1.50000
AFIX 0
C24 1 -0.066676 0.661511 0.209544 11.00000 0.02401 0.02165 =
0.02031 0.00515 0.00790 0.00769
AFIX 23
H24A 2 -0.025462 0.711413 0.242761 11.00000 -1.20000
H24B 2 -0.038476 0.636333 0.176469 11.00000 -1.20000
AFIX 0
C25 1 -0.139502 0.764938 0.180997 11.00000 0.03273 0.03000 =
0.03252 0.00991 0.01164 0.01408
AFIX 137
H25A 2 -0.178023 0.720593 0.145151 11.00000 -1.50000
H25B 2 -0.116677 0.850556 0.167257 11.00000 -1.50000
H25C 2 -0.169442 0.788477 0.212693 11.00000 -1.50000
AFIX 0
C26 1 -0.127420 0.412395 0.391427 11.00000 0.02852 0.03460 =
0.03328 0.01313 0.02098 0.01104
AFIX 137
H26A 2 -0.152178 0.334542 0.364131 11.00000 -1.50000
H26B 2 -0.171657 0.465871 0.403219 11.00000 -1.50000
H26C 2 -0.088824 0.375425 0.429130 11.00000 -1.50000
AFIX 0
C27 1 -0.047919 0.635721 0.400601 11.00000 0.02910 0.03368 =
0.07110 -0.02648 0.02400 -0.00123
AFIX 137
H27A 2 -0.008350 0.602206 0.438576 11.00000 -1.50000
H27B 2 -0.095512 0.680296 0.411782 11.00000 -1.50000
H27C 2 -0.020234 0.703947 0.379430 11.00000 -1.50000
AFIX 0
C28 1 0.166986 0.701868 0.447642 11.00000 0.02965 0.02232 =
0.02505 -0.00300 0.00764 -0.00527
AFIX 137
H28A 2 0.118131 0.704263 0.465126 11.00000 -1.50000
H28B 2 0.175330 0.794521 0.431092 11.00000 -1.50000
H28C 2 0.216454 0.676067 0.480478 11.00000 -1.50000
AFIX 0
C29 1 0.191161 0.375334 0.463966 11.00000 0.01689 0.02645 =
0.01595 -0.00274 0.00250 0.00079
AFIX 43
H29 2 0.239218 0.425518 0.485653 11.00000 -1.20000
AFIX 0
C30 1 0.179785 0.236391 0.481512 11.00000 0.02205 0.02745 =
0.01280 0.00333 0.00298 0.00792
AFIX 43
H30 2 0.218713 0.194897 0.515781 11.00000 -1.20000
AFIX 0
C31 1 0.110268 0.158971 0.447958 11.00000 0.02667 0.01629 =
0.01713 0.00336 0.00819 0.00443
AFIX 43
H31 2 0.104329 0.063903 0.458699 11.00000 -1.20000
AFIX 0
C32 1 0.048784 0.221022 0.398199 11.00000 0.02010 0.01633 =
0.01409 0.00015 0.00807 0.00200
C33 1 -0.023366 0.128159 0.360335 11.00000 0.02225 0.01571 =
0.01954 0.00165 0.00476 -0.00019
AFIX 13
H33 2 -0.064455 0.191056 0.332061 11.00000 -1.20000
AFIX 0
C34 1 0.010530 0.022635 0.318364 11.00000 0.03198 0.02112 =
0.02271 -0.00249 0.00583 -0.00062
AFIX 137
H34A 2 0.039356 0.074339 0.291661 11.00000 -1.50000
H34B 2 -0.036130 -0.029996 0.292169 11.00000 -1.50000
H34C 2 0.049586 -0.042505 0.344985 11.00000 -1.50000
AFIX 0
C35 1 -0.070844 0.046939 0.402636 11.00000 0.03254 0.02100 =
0.03105 0.00184 0.01214 -0.00557
AFIX 137
H35A 2 -0.033082 -0.021098 0.428497 11.00000 -1.50000
H35B 2 -0.118784 -0.002285 0.376172 11.00000 -1.50000
H35C 2 -0.090328 0.113454 0.429668 11.00000 -1.50000
AFIX 0
B1 4 0.056939 0.385450 0.243950 11.00000 0.01287 0.01500 =
0.01334 0.00242 0.00057 0.00085
AFIX 43
H1 2 0.103803 0.346168 0.272795 11.00000 -1.20000
AFIX 0
HKLF 4
REM GB_MM3_0m in P2(1)/n
REM R1 = 0.0492 for 4873 Fo > 4sig(Fo) and 0.0786 for all 6500 data
REM 359 parameters refined using 0 restraints
END
WGHT 0.0937 0.5412
REM Instructions for potential hydrogen bonds
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak 0.391, deepest hole -0.579, 1-sigma level 0.169
Q1 1 0.8090 0.8858 0.0416 11.00000 0.05 0.39
Q2 1 0.7641 0.8459 0.0627 11.00000 0.05 0.37
Q3 1 0.7950 0.8396 0.0934 11.00000 0.05 0.36
Q4 1 0.7981 0.7688 0.0615 11.00000 0.05 0.35
Q5 1 0.2569 0.7136 0.4794 11.00000 0.05 0.34
;
_shelx_res_checksum 85174
_database_code_depnum_ccdc_archive 'CCDC 1001684'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_shelxl
_audit_creation_date 2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C38 H64 B F3 N3 O3 S, C24 H20 B'
_chemical_formula_sum 'C62 H84 B2 F3 N3 O3 S'
_chemical_formula_weight 1030.00
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
_cell_length_a 22.260(12)
_cell_length_b 13.788(7)
_cell_length_c 19.769(10)
_cell_angle_alpha 90.00
_cell_angle_beta 106.570(7)
_cell_angle_gamma 90.00
_cell_volume 5816(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used ?
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max ?
_cell_measurement_theta_min ?
_exptl_absorpt_coefficient_mu 0.112
_exptl_absorpt_correction_T_max 0.9884
_exptl_absorpt_correction_T_min 0.9700
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.176
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description ?
_exptl_crystal_F_000 2216
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.11
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.1417
_diffrn_reflns_av_unetI/netI 0.2426
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 24181
_diffrn_reflns_theta_full 23.28
_diffrn_reflns_theta_max 23.28
_diffrn_reflns_theta_min 2.41
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number ?
_reflns_number_gt 3230
_reflns_number_total 8342
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.349
_refine_diff_density_min -0.300
_refine_diff_density_rms 0.048
_refine_ls_extinction_coef 0.00202(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.787
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 763
_refine_ls_number_reflns 8342
_refine_ls_number_restraints 79
_refine_ls_R_factor_all 0.1833
_refine_ls_R_factor_gt 0.0522
_refine_ls_restrained_S_all 0.821
_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^)+(0.0209P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0744
_refine_ls_wR_factor_ref 0.0995
_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
;
1. Shared sites
{O2A, O2B}
2. Others
Fixed Sof: S1A(0.6) O1A(0.6) O2A(0.6) O3A(0.6) C3A(0.6) F1A(0.6) F2A(0.6)
F3A(0.6) H1A(0.6) S1B(0.4) O1B(0.4) O2B(0.4) O3B(0.4) C3B(0.4) F1B(0.4)
F2B(0.4) F3B(0.4) H1B(0.4)
Fixed Uiso: H3A(0.032) H3B(0.032) H10(0.033) H11(0.035) H12(0.035)
H14A(0.029) H14B(0.029) H15A(0.07) H15B(0.07) H15C(0.07) H16A(0.033)
H16B(0.033) H17A(0.071) H17B(0.071) H17C(0.071) H18A(0.061) H18B(0.061)
H18C(0.061) H19A(0.06) H19B(0.06) H19C(0.06) H20A(0.053) H20B(0.053)
H20C(0.053) H21(0.071) H22A(0.256) H22B(0.256) H22C(0.256) H23(0.034)
H24A(0.067) H24B(0.067) H24C(0.067) H25A(0.073) H25B(0.073) H25C(0.073)
H26(0.035) H27A(0.069) H27B(0.069) H27C(0.069) H28A(0.062) H28B(0.062)
H28C(0.062) H29(0.037) H30A(0.052) H30B(0.052) H30C(0.052) H31A(0.067)
H31B(0.067) H31C(0.067) H32(0.027) H33A(0.05) H33B(0.05) H33C(0.05)
H34A(0.053) H34B(0.053) H34C(0.053) H35(0.033) H36A(0.058) H36B(0.058)
H36C(0.058) H37A(0.054) H37B(0.054) H37C(0.054) H112(0.036) H113(0.043)
H114(0.045) H115(0.041) H116(0.036) H118(0.03) H119(0.036) H120(0.037)
H121(0.034) H122(0.033) H124(0.032) H125(0.029) H126(0.032) H127(0.029)
H128(0.028) H130(0.034) H131(0.044) H132(0.044) H133(0.042) H134(0.038)
Fixed X: H3A(0.8333) H3B(0.769) H10(0.9368) H11(1.0384) H12(1.0574)
H14A(0.7093) H14B(0.6961) H15A(0.6625) H15B(0.6205) H15C(0.6737) H16A(0.7558)
H16B(0.7641) H17A(0.8758) H17B(0.8456) H17C(0.8638) H18A(0.7792) H18B(0.7593)
H18C(0.8182) H19A(0.9208) H19B(0.8809) H19C(0.9187) H20A(0.7094) H20B(0.6798)
H20C(0.7438) H21(0.6256) H22A(0.6872) H22B(0.6142) H22C(0.6477) H23(0.6016)
H24A(0.5713) H24B(0.5121) H24C(0.5407) H25A(0.5521) H25B(0.5263) H25C(0.5934)
H26(0.8153) H27A(0.7389) H27B(0.8031) H27C(0.7448) H28A(0.8123) H28B(0.872)
H28C(0.8445) H29(0.713) H30A(0.6669) H30B(0.6651) H30C(0.7308) H31A(0.6362)
H31B(0.603) H31C(0.6095) H32(0.7965) H33A(0.848) H33B(0.8387) H33C(0.7791)
H34A(0.8395) H34B(0.768) H34C(0.8166) H35(0.9455) H36A(1.0753) H36B(1.0406)
H36C(1.0239) H37A(0.9733) H37B(1.014) H37C(1.0445) H112(0.7274) H113(0.8345)
H114(0.8954) H115(0.848) H116(0.7413) H118(0.6863) H119(0.6571) H120(0.5765)
H121(0.5266) H122(0.5567) H124(0.5279) H125(0.4939) H126(0.5668) H127(0.6738)
H128(0.7067) H130(0.6064) H131(0.5601) H132(0.5295) H133(0.5509) H134(0.6008)
Fixed Y: H3A(0.2729) H3B(0.3327) H10(0.6035) H11(0.5483) H12(0.4162)
H14A(0.3651) H14B(0.2594) H15A(0.2076) H15B(0.2956) H15C(0.315) H16A(0.1336)
H16B(0.1254) H17A(0.1362) H17B(0.0408) H17C(0.1308) H18A(0.5108) H18B(0.4824)
H18C(0.5521) H19A(0.3759) H19B(0.4571) H19C(0.4845) H20A(0.4506) H20B(0.3535)
H20C(0.3488) H21(0.3743) H22A(0.4321) H22B(0.4101) H22C(0.4932) H23(0.1412)
H24A(0.2346) H24B(0.2063) H24C(0.3135) H25A(0.2941) H25B(0.1852) H25C(0.2071)
H26(0.0271) H27A(-0.0632) H27B(-0.1225) H27C(-0.1493) H28A(-0.1268) H28B(-
0.0937) H28C(-0.024) H29(-0.0987) H30A(0.0729) H30B(-0.0335) H30C(0.02) H31A(-
0.0865) H31B(-0.0899) H31C(0.011) H32(0.5066) H33A(0.6958) H33B(0.6559)
H33C(0.6737) H34A(0.5924) H34B(0.5687) H34C(0.4822) H35(0.2816) H36A(0.3382)
H36B(0.274) H36C(0.3866) H37A(0.1984) H37B(0.1596) H37C(0.2329) H112(0.9485)
H113(0.9639) H114(0.8266) H115(0.6739) H116(0.66) H118(0.7011) H119(0.5641)
H120(0.464) H121(0.5028) H122(0.6406) H124(0.8004) H125(0.8078) H126(0.8067)
H127(0.7977) H128(0.7863) H130(0.9749) H131(1.1069) H132(1.098) H133(0.9573)
H134(0.8275)
Fixed Z: H3A(0.3025) H3B(0.2883) H10(0.0758) H11(0.1243) H12(0.2001)
H14A(0.1475) H14B(0.1134) H15A(0.2114) H15B(0.1706) H15C(0.2432) H16A(0.2344)
H16B(0.1571) H17A(0.2091) H17B(0.2321) H17C(0.2851) H18A(0.2799) H18B(0.198)
H18C(0.2296) H19A(0.3307) H19B(0.3566) H19C(0.3015) H20A(-0.1188) H20B(-
0.1591) H20C(-0.0965) H21(-0.0982) H22A(0.0244) H22B(-0.0096) H22C(-0.0423)
H23(-0.0711) H24A(0.0137) H24B(-0.0509) H24C(-0.0455) H25A(-0.1679) H25B(-
0.1731) H25C(-0.1844) H26(0.0886) H27A(0.1247) H27B(0.1389) H27C(0.0727) H28A(-
0.0089) H28B(0.0535) H28C(-0.0129) H29(-0.0494) H30A(-0.1263) H30B(-0.1591)
H30C(-0.1266) H31A(0.0081) H31B(-0.0752) H31C(-0.0336) H32(0.1037)
H33A(0.0934) H33B(0.1658) H33C(0.0992) H34A(-0.0065) H34B(-0.0114) H34C(-
0.0083) H35(0.2599) H36A(0.3037) H36B(0.3487) H36C(0.3356) H37A(0.1675)
H37B(0.2429) H37C(0.1992) H112(0.2828) H113(0.3389) H114(0.3814) H115(0.3647)
H116(0.3135) H118(0.1687) H119(0.1001) H120(0.1127) H121(0.1991) H122(0.2688)
H124(0.2968) H125(0.3974) H126(0.5094) H127(0.5186) H128(0.4165) H130(0.301)
H131(0.2337) H132(0.1103) H133(0.0564) H134(0.1236)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8261(3) 0.2548(5) 0.0817(3) 0.049(2) Uani 1 1 d D . .
N1 N 0.85436(16) 0.3752(3) 0.18802(17) 0.0184(9) Uani 1 1 d . . .
N2 N 0.65656(19) 0.2594(3) -0.0530(2) 0.0295(11) Uani 1 1 d . . .
N3 N 0.73591(17) 0.0246(3) 0.00641(19) 0.0250(10) Uani 1 1 d . . .
C1 C 0.8214(2) 0.3032(3) 0.1547(2) 0.0221(12) Uani 1 1 d . . .
C2 C 0.7786(2) 0.2649(3) 0.1973(2) 0.0194(12) Uani 1 1 d . . .
C3 C 0.80387(19) 0.3160(3) 0.2687(2) 0.0266(13) Uani 1 1 d . A .
H3A H 0.8333 0.2729 0.3025 0.032 Uiso 1 1 calc R . .
H3B H 0.7690 0.3327 0.2883 0.032 Uiso 1 1 calc R . .
C4 C 0.8377(2) 0.4083(3) 0.2562(2) 0.0246(13) Uani 1 1 d . A .
C5 C 0.7629(2) 0.2057(3) 0.0360(2) 0.0231(12) Uani 1 1 d . A .
C6 C 0.7335(2) 0.1199(4) 0.0083(2) 0.0246(12) Uani 1 1 d . . .
C7 C 0.7045(2) 0.2083(4) -0.0128(2) 0.0229(12) Uani 1 1 d . A .
C8 C 0.9062(2) 0.4257(3) 0.1684(2) 0.0195(12) Uani 1 1 d . . .
C9 C 0.8929(2) 0.5053(3) 0.1228(2) 0.0231(12) Uani 1 1 d . . .
C10 C 0.9440(2) 0.5495(3) 0.1070(2) 0.0274(13) Uani 1 1 d . . .
H10 H 0.9368 0.6035 0.0758 0.033 Uiso 1 1 calc R . .
C11 C 1.0045(2) 0.5168(3) 0.1355(2) 0.0292(13) Uani 1 1 d . . .
H11 H 1.0384 0.5483 0.1243 0.035 Uiso 1 1 calc R A .
C12 C 1.0156(2) 0.4380(3) 0.1804(2) 0.0295(13) Uani 1 1 d . . .
H12 H 1.0574 0.4162 0.2001 0.035 Uiso 1 1 calc R . .
C13 C 0.9670(2) 0.3896(3) 0.1976(2) 0.0217(12) Uani 1 1 d . . .
C14 C 0.70982(18) 0.2951(3) 0.1587(2) 0.0240(12) Uani 1 1 d . . .
H14A H 0.7093 0.3651 0.1475 0.029 Uiso 1 1 calc R . .
H14B H 0.6961 0.2594 0.1134 0.029 Uiso 1 1 calc R . .
C15 C 0.6624(2) 0.2767(4) 0.1996(2) 0.0464(16) Uani 1 1 d . . .
H15A H 0.6625 0.2076 0.2114 0.070 Uiso 1 1 calc R A .
H15B H 0.6205 0.2956 0.1706 0.070 Uiso 1 1 calc R . .
H15C H 0.6737 0.3150 0.2432 0.070 Uiso 1 1 calc R . .
C16 C 0.7823(2) 0.1541(3) 0.2044(2) 0.0279(13) Uani 1 1 d . . .
H16A H 0.7558 0.1336 0.2344 0.033 Uiso 1 1 calc R . .
H16B H 0.7641 0.1254 0.1571 0.033 Uiso 1 1 calc R . .
C17 C 0.8477(2) 0.1117(3) 0.2354(2) 0.0470(15) Uani 1 1 d . . .
H17A H 0.8758 0.1362 0.2091 0.071 Uiso 1 1 calc R A .
H17B H 0.8456 0.0408 0.2321 0.071 Uiso 1 1 calc R . .
H17C H 0.8638 0.1308 0.2851 0.071 Uiso 1 1 calc R . .
C18 C 0.7948(2) 0.4962(3) 0.2394(2) 0.0407(15) Uani 1 1 d . . .
H18A H 0.7792 0.5108 0.2799 0.061 Uiso 1 1 calc R A .
H18B H 0.7593 0.4824 0.1980 0.061 Uiso 1 1 calc R . .
H18C H 0.8182 0.5521 0.2296 0.061 Uiso 1 1 calc R . .
C19 C 0.8945(2) 0.4337(3) 0.3166(2) 0.0399(15) Uani 1 1 d . . .
H19A H 0.9208 0.3759 0.3307 0.060 Uiso 1 1 calc R A .
H19B H 0.8809 0.4571 0.3566 0.060 Uiso 1 1 calc R . .
H19C H 0.9187 0.4845 0.3015 0.060 Uiso 1 1 calc R . .
C20 C 0.7031(2) 0.3811(3) -0.1134(2) 0.0353(14) Uani 1 1 d . . .
H20A H 0.7094 0.4506 -0.1188 0.053 Uiso 1 1 calc R . .
H20B H 0.6798 0.3535 -0.1591 0.053 Uiso 1 1 calc R . .
H20C H 0.7438 0.3488 -0.0965 0.053 Uiso 1 1 calc R . .
C21 C 0.6668(3) 0.3662(4) -0.0616(3) 0.0590(19) Uani 1 1 d . . .
H21 H 0.6256 0.3743 -0.0982 0.071 Uiso 1 1 calc R . .
C22 C 0.6531(4) 0.4292(4) -0.0197(4) 0.170(5) Uani 1 1 d . . .
H22A H 0.6872 0.4321 0.0244 0.256 Uiso 1 1 calc R . .
H22B H 0.6142 0.4101 -0.0096 0.256 Uiso 1 1 calc R . .
H22C H 0.6477 0.4932 -0.0423 0.256 Uiso 1 1 calc R . .
C23 C 0.5947(2) 0.2124(3) -0.0793(2) 0.0286(13) Uani 1 1 d . . .
H23 H 0.6016 0.1412 -0.0711 0.034 Uiso 1 1 calc R . .
C24 C 0.5507(2) 0.2446(3) -0.0367(2) 0.0449(16) Uani 1 1 d . . .
H24A H 0.5713 0.2346 0.0137 0.067 Uiso 1 1 calc R . .
H24B H 0.5121 0.2063 -0.0509 0.067 Uiso 1 1 calc R . .
H24C H 0.5407 0.3135 -0.0455 0.067 Uiso 1 1 calc R . .
C25 C 0.5639(2) 0.2259(4) -0.1582(2) 0.0485(16) Uani 1 1 d . . .
H25A H 0.5521 0.2941 -0.1679 0.073 Uiso 1 1 calc R . .
H25B H 0.5263 0.1852 -0.1731 0.073 Uiso 1 1 calc R . .
H25C H 0.5934 0.2071 -0.1844 0.073 Uiso 1 1 calc R . .
C26 C 0.7905(2) -0.0240(3) 0.0566(2) 0.0289(13) Uani 1 1 d . . .
H26 H 0.8153 0.0271 0.0886 0.035 Uiso 1 1 calc R A .
C27 C 0.7672(2) -0.0963(3) 0.1024(2) 0.0460(15) Uani 1 1 d . . .
H27A H 0.7389 -0.0632 0.1247 0.069 Uiso 1 1 calc R . .
H27B H 0.8031 -0.1225 0.1389 0.069 Uiso 1 1 calc R . .
H27C H 0.7448 -0.1493 0.0727 0.069 Uiso 1 1 calc R . .
C28 C 0.8337(2) -0.0713(3) 0.0187(2) 0.0411(15) Uani 1 1 d . . .
H28A H 0.8123 -0.1268 -0.0089 0.062 Uiso 1 1 calc R . .
H28B H 0.8720 -0.0937 0.0535 0.062 Uiso 1 1 calc R . .
H28C H 0.8445 -0.0240 -0.0129 0.062 Uiso 1 1 calc R . .
C29 C 0.6930(2) -0.0337(3) -0.0502(2) 0.0305(13) Uani 1 1 d . . .
H29 H 0.7130 -0.0987 -0.0494 0.037 Uiso 1 1 calc R A .
C30 C 0.6885(2) 0.0103(3) -0.1219(2) 0.0347(14) Uani 1 1 d . . .
H30A H 0.6669 0.0729 -0.1263 0.052 Uiso 1 1 calc R . .
H30B H 0.6651 -0.0335 -0.1591 0.052 Uiso 1 1 calc R . .
H30C H 0.7308 0.0200 -0.1266 0.052 Uiso 1 1 calc R . .
C31 C 0.6298(2) -0.0513(3) -0.0365(2) 0.0447(15) Uani 1 1 d . . .
H31A H 0.6362 -0.0865 0.0081 0.067 Uiso 1 1 calc R . .
H31B H 0.6030 -0.0899 -0.0752 0.067 Uiso 1 1 calc R . .
H31C H 0.6095 0.0110 -0.0336 0.067 Uiso 1 1 calc R . .
C32 C 0.8280(2) 0.5474(3) 0.0894(2) 0.0226(12) Uani 1 1 d . . .
H32 H 0.7965 0.5066 0.1037 0.027 Uiso 1 1 calc R . .
C33 C 0.8230(2) 0.6529(3) 0.1142(2) 0.0334(13) Uani 1 1 d . . .
H33A H 0.8480 0.6958 0.0934 0.050 Uiso 1 1 calc R A .
H33B H 0.8387 0.6559 0.1658 0.050 Uiso 1 1 calc R . .
H33C H 0.7791 0.6737 0.0992 0.050 Uiso 1 1 calc R . .
C34 C 0.8115(2) 0.5477(3) 0.0085(2) 0.0356(14) Uani 1 1 d . . .
H34A H 0.8395 0.5924 -0.0065 0.053 Uiso 1 1 calc R A .
H34B H 0.7680 0.5687 -0.0114 0.053 Uiso 1 1 calc R . .
H34C H 0.8166 0.4822 -0.0083 0.053 Uiso 1 1 calc R . .
C35 C 0.9838(2) 0.3018(3) 0.2466(2) 0.0271(12) Uani 1 1 d . . .
H35 H 0.9455 0.2816 0.2599 0.033 Uiso 1 1 calc R . .
C36 C 1.03564(19) 0.3275(3) 0.3149(2) 0.0389(14) Uani 1 1 d . . .
H36A H 1.0753 0.3382 0.3037 0.058 Uiso 1 1 calc R A .
H36B H 1.0406 0.2740 0.3487 0.058 Uiso 1 1 calc R . .
H36C H 1.0239 0.3866 0.3356 0.058 Uiso 1 1 calc R . .
C37 C 1.0059(2) 0.2154(3) 0.2108(2) 0.0360(14) Uani 1 1 d . . .
H37A H 0.9733 0.1984 0.1675 0.054 Uiso 1 1 calc R A .
H37B H 1.0140 0.1596 0.2429 0.054 Uiso 1 1 calc R . .
H37C H 1.0445 0.2329 0.1992 0.054 Uiso 1 1 calc R . .
S1A S 0.87430(10) 0.27669(17) -0.02613(10) 0.0213(5) Uani 0.60 1 d PD A 1
O1A O 0.8591(2) 0.3125(4) 0.0387(2) 0.0171(13) Uani 0.60 1 d PD A 1
O2A O 0.8451(3) 0.1839(4) -0.0506(3) 0.021(3) Uani 0.60 1 d PDU A 1
O3A O 0.8687(4) 0.3552(4) -0.0771(3) 0.054(3) Uani 0.60 1 d PD A 1
C3A C 0.9581(4) 0.2504(6) 0.0035(4) 0.039(3) Uani 0.60 1 d PDU A 1
F1A F 0.9908(6) 0.3250(8) 0.0373(6) 0.121(7) Uani 0.60 1 d PD A 1
F2A F 0.9685(3) 0.1728(6) 0.0453(4) 0.096(4) Uani 0.60 1 d PD A 1
F3A F 0.9790(6) 0.2311(8) -0.0521(5) 0.065(4) Uani 0.60 1 d PD A 1
H1A H 0.867(3) 0.189(4) 0.105(3) 0.000(15) Uiso 0.60 1 d PD B 1
S1B S 0.89592(18) 0.1880(3) 0.00964(19) 0.0444(10) Uani 0.40 1 d PD A 2
O1B O 0.8775(4) 0.2268(7) 0.0709(4) 0.045(3) Uani 0.40 1 d PD A 2
O2B O 0.8443(5) 0.1754(11) -0.0542(5) 0.114(10) Uani 0.40 1 d PD A 2
O3B O 0.9437(5) 0.1122(8) 0.0296(6) 0.071(5) Uani 0.40 1 d PD A 2
C3B C 0.9374(5) 0.2912(7) -0.0122(5) 0.039(4) Uani 0.40 1 d PDU A 2
F1B F 0.8989(4) 0.3659(7) -0.0329(4) 0.076(4) Uani 0.40 1 d PD A 2
F2B F 0.9847(6) 0.3156(9) 0.0432(7) 0.049(5) Uani 0.40 1 d PD A 2
F3B F 0.9611(8) 0.2662(12) -0.0644(7) 0.053(5) Uani 0.40 1 d PD A 2
H1B H 0.823(4) 0.337(4) 0.050(4) 0.000(15) Uiso 0.40 1 d PD C 2
B2 B 0.6438(2) 0.7916(4) 0.2704(3) 0.0217(14) Uani 1 1 d . . .
C111 C 0.7200(2) 0.8029(3) 0.2945(2) 0.0220(12) Uani 1 1 d . . .
C112 C 0.7509(2) 0.8921(4) 0.3011(2) 0.0296(13) Uani 1 1 d . . .
H112 H 0.7274 0.9485 0.2828 0.036 Uiso 1 1 calc R . .
C113 C 0.8156(2) 0.9016(4) 0.3338(2) 0.0356(14) Uani 1 1 d . . .
H113 H 0.8345 0.9639 0.3389 0.043 Uiso 1 1 calc R . .
C114 C 0.8519(2) 0.8204(4) 0.3586(2) 0.0372(15) Uani 1 1 d . . .
H114 H 0.8954 0.8266 0.3814 0.045 Uiso 1 1 calc R . .
C115 C 0.8236(2) 0.7306(4) 0.3497(2) 0.0343(14) Uani 1 1 d . . .
H115 H 0.8480 0.6739 0.3647 0.041 Uiso 1 1 calc R . .
C116 C 0.7595(2) 0.7229(4) 0.3187(2) 0.0299(13) Uani 1 1 d . . .
H116 H 0.7413 0.6600 0.3135 0.036 Uiso 1 1 calc R . .
C117 C 0.6242(2) 0.6900(3) 0.2269(2) 0.0213(12) Uani 1 1 d . . .
C118 C 0.6533(2) 0.6620(3) 0.1755(2) 0.0248(12) Uani 1 1 d . . .
H118 H 0.6863 0.7011 0.1687 0.030 Uiso 1 1 calc R . .
C119 C 0.6360(2) 0.5796(3) 0.1342(2) 0.0304(13) Uani 1 1 d . . .
H119 H 0.6571 0.5641 0.1001 0.036 Uiso 1 1 calc R . .
C120 C 0.5886(2) 0.5197(3) 0.1416(2) 0.0308(13) Uani 1 1 d . . .
H120 H 0.5765 0.4640 0.1127 0.037 Uiso 1 1 calc R . .
C121 C 0.5591(2) 0.5431(3) 0.1924(2) 0.0284(13) Uani 1 1 d . . .
H121 H 0.5266 0.5028 0.1991 0.034 Uiso 1 1 calc R . .
C122 C 0.5773(2) 0.6265(3) 0.2340(2) 0.0274(13) Uani 1 1 d . . .
H122 H 0.5567 0.6406 0.2688 0.033 Uiso 1 1 calc R . .
C123 C 0.62170(19) 0.7933(3) 0.3438(2) 0.0200(11) Uani 1 1 d . . .
C124 C 0.5583(2) 0.7994(3) 0.3417(2) 0.0271(12) Uani 1 1 d . . .
H124 H 0.5279 0.8004 0.2968 0.032 Uiso 1 1 calc R . .
C125 C 0.5375(2) 0.8041(3) 0.4019(2) 0.0243(12) Uani 1 1 d . . .
H125 H 0.4939 0.8078 0.3974 0.029 Uiso 1 1 calc R . .
C126 C 0.5806(2) 0.8033(3) 0.4682(2) 0.0264(12) Uani 1 1 d . . .
H126 H 0.5668 0.8067 0.5094 0.032 Uiso 1 1 calc R . .
C127 C 0.6437(2) 0.7976(3) 0.4735(2) 0.0242(12) Uani 1 1 d . . .
H127 H 0.6738 0.7977 0.5186 0.029 Uiso 1 1 calc R . .
C128 C 0.6631(2) 0.7917(3) 0.4117(2) 0.0230(12) Uani 1 1 d . . .
H128 H 0.7067 0.7863 0.4165 0.028 Uiso 1 1 calc R . .
C129 C 0.6098(2) 0.8832(3) 0.2212(2) 0.0229(12) Uani 1 1 d . . .
C130 C 0.5959(2) 0.9702(3) 0.2510(2) 0.0281(13) Uani 1 1 d . . .
H130 H 0.6064 0.9749 0.3010 0.034 Uiso 1 1 calc R . .
C131 C 0.5675(2) 1.0493(3) 0.2109(3) 0.0363(14) Uani 1 1 d . . .
H131 H 0.5601 1.1069 0.2337 0.044 Uiso 1 1 calc R . .
C132 C 0.5499(2) 1.0448(4) 0.1380(3) 0.0363(14) Uani 1 1 d . . .
H132 H 0.5295 1.0980 0.1103 0.044 Uiso 1 1 calc R . .
C133 C 0.5625(2) 0.9617(4) 0.1065(3) 0.0353(14) Uani 1 1 d . . .
H133 H 0.5509 0.9573 0.0564 0.042 Uiso 1 1 calc R . .
C134 C 0.5921(2) 0.8835(4) 0.1472(2) 0.0314(13) Uani 1 1 d . . .
H134 H 0.6008 0.8275 0.1236 0.038 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
B1 0.048(5) 0.071(6) 0.035(4) -0.025(4) 0.025(4) -0.034(5)
N1 0.017(2) 0.022(3) 0.014(2) 0.004(2) 0.0018(19) 0.007(2)
N2 0.034(3) 0.025(3) 0.034(3) 0.003(2) 0.018(2) 0.001(2)
N3 0.025(2) 0.024(3) 0.023(2) -0.001(2) 0.002(2) 0.006(2)
C1 0.024(3) 0.017(3) 0.021(3) 0.001(3) 0.001(2) 0.002(3)
C2 0.026(3) 0.022(3) 0.011(3) 0.004(2) 0.006(2) 0.004(2)
C3 0.024(3) 0.033(3) 0.024(3) 0.008(3) 0.011(2) 0.004(3)
C4 0.033(3) 0.035(4) 0.006(3) -0.008(3) 0.006(2) -0.002(3)
C5 0.031(3) 0.023(3) 0.018(3) -0.003(3) 0.012(3) -0.003(3)
C6 0.029(3) 0.032(4) 0.014(3) 0.001(3) 0.009(2) 0.000(3)
C7 0.028(3) 0.022(4) 0.021(3) -0.003(3) 0.012(3) -0.003(3)
C8 0.018(3) 0.024(3) 0.016(3) -0.006(3) 0.004(2) -0.004(2)
C9 0.026(3) 0.021(3) 0.021(3) -0.002(3) 0.006(3) 0.003(3)
C10 0.034(3) 0.026(3) 0.023(3) -0.001(3) 0.009(3) -0.002(3)
C11 0.031(3) 0.029(4) 0.027(3) -0.002(3) 0.006(3) -0.006(3)
C12 0.023(3) 0.035(4) 0.028(3) 0.000(3) 0.003(3) 0.004(3)
C13 0.023(3) 0.025(3) 0.016(3) -0.003(3) 0.003(2) -0.003(3)
C14 0.023(3) 0.025(3) 0.023(3) 0.001(3) 0.006(2) -0.001(3)
C15 0.029(3) 0.076(4) 0.033(3) 0.003(3) 0.008(3) -0.005(3)
C16 0.032(3) 0.034(4) 0.017(3) 0.002(3) 0.007(3) 0.002(3)
C17 0.047(4) 0.033(4) 0.048(4) 0.002(3) -0.008(3) 0.008(3)
C18 0.061(4) 0.035(4) 0.035(3) -0.002(3) 0.027(3) 0.005(3)
C19 0.050(4) 0.055(4) 0.019(3) -0.011(3) 0.016(3) -0.015(3)
C20 0.040(3) 0.036(4) 0.028(3) -0.002(3) 0.006(3) -0.008(3)
C21 0.093(5) 0.023(4) 0.088(5) 0.018(4) 0.069(4) 0.011(3)
C22 0.375(13) 0.036(5) 0.209(9) -0.053(5) 0.259(10) -0.063(6)
C23 0.031(3) 0.030(3) 0.025(3) -0.003(3) 0.009(3) 0.000(3)
C24 0.042(4) 0.046(4) 0.053(4) -0.017(3) 0.024(3) -0.015(3)
C25 0.037(3) 0.083(5) 0.025(3) 0.020(3) 0.008(3) 0.015(3)
C26 0.029(3) 0.027(3) 0.026(3) -0.002(3) -0.001(3) 0.003(3)
C27 0.054(4) 0.040(4) 0.042(3) 0.014(3) 0.011(3) 0.009(3)
C28 0.032(3) 0.048(4) 0.038(3) -0.003(3) 0.003(3) 0.015(3)
C29 0.030(3) 0.022(3) 0.034(3) -0.006(3) -0.001(3) -0.001(3)
C30 0.034(3) 0.037(4) 0.028(3) -0.007(3) 0.000(3) 0.001(3)
C31 0.030(3) 0.029(3) 0.074(4) 0.005(3) 0.013(3) -0.005(3)
C32 0.025(3) 0.021(3) 0.018(3) 0.002(3) 0.000(2) -0.002(2)
C33 0.031(3) 0.027(3) 0.037(3) 0.002(3) 0.001(3) 0.005(3)
C34 0.039(3) 0.037(4) 0.024(3) 0.007(3) -0.004(3) 0.006(3)
C35 0.025(3) 0.033(3) 0.019(3) 0.003(3) 0.000(2) -0.001(3)
C36 0.029(3) 0.051(4) 0.030(3) 0.006(3) -0.002(3) 0.001(3)
C37 0.034(3) 0.038(4) 0.034(3) 0.005(3) 0.006(3) 0.001(3)
S1A 0.0247(13) 0.0273(16) 0.0125(12) -0.0023(12) 0.0063(10) -0.0010(12)
O1A 0.029(4) 0.009(3) 0.015(3) 0.003(3) 0.010(3) 0.002(3)
O2A 0.023(5) 0.027(5) 0.012(5) -0.012(4) 0.004(4) -0.010(4)
O3A 0.102(7) 0.053(5) 0.013(4) 0.005(4) 0.024(4) 0.025(4)
C3A 0.034(5) 0.049(5) 0.034(5) -0.003(4) 0.008(4) 0.008(4)
F1A 0.059(9) 0.225(16) 0.091(9) -0.119(9) 0.043(7) -0.047(8)
F2A 0.093(6) 0.159(9) 0.038(4) 0.009(6) 0.021(4) 0.101(7)
F3A 0.046(5) 0.111(11) 0.047(5) -0.026(5) 0.029(4) 0.002(6)
S1B 0.051(3) 0.049(3) 0.043(2) -0.010(2) 0.030(2) -0.003(2)
O1B 0.039(7) 0.073(9) 0.029(6) -0.030(6) 0.018(5) -0.012(6)
O2B 0.118(18) 0.18(2) 0.054(14) -0.052(13) 0.042(13) -0.037(15)
O3B 0.083(10) 0.078(10) 0.055(9) -0.025(8) 0.027(7) 0.031(8)
C3B 0.048(6) 0.039(6) 0.034(6) -0.009(5) 0.018(5) 0.006(5)
F1B 0.128(11) 0.058(7) 0.081(8) 0.047(6) 0.092(9) 0.043(7)
F2B 0.011(7) 0.079(11) 0.050(10) -0.005(9) -0.001(7) -0.027(7)
F3B 0.083(14) 0.047(9) 0.054(8) -0.026(6) 0.061(9) -0.026(7)
B2 0.019(3) 0.023(4) 0.023(3) 0.003(3) 0.005(3) 0.001(3)
C111 0.029(3) 0.023(3) 0.017(3) 0.003(3) 0.011(2) -0.002(3)
C112 0.036(4) 0.036(4) 0.020(3) 0.000(3) 0.013(3) 0.000(3)
C113 0.034(4) 0.048(4) 0.028(3) -0.007(3) 0.012(3) -0.022(3)
C114 0.020(3) 0.067(5) 0.024(3) -0.002(3) 0.005(3) 0.001(3)
C115 0.030(4) 0.044(4) 0.030(3) -0.003(3) 0.009(3) 0.001(3)
C116 0.029(3) 0.035(4) 0.026(3) -0.003(3) 0.009(3) -0.009(3)
C117 0.025(3) 0.019(3) 0.017(3) 0.003(3) 0.002(2) 0.004(3)
C118 0.031(3) 0.022(3) 0.020(3) -0.002(3) 0.004(3) -0.006(3)
C119 0.036(3) 0.031(4) 0.025(3) -0.001(3) 0.011(3) 0.001(3)
C120 0.040(4) 0.024(3) 0.024(3) -0.007(3) 0.001(3) -0.004(3)
C121 0.023(3) 0.028(3) 0.029(3) -0.002(3) 0.000(3) -0.011(3)
C122 0.029(3) 0.031(4) 0.021(3) 0.008(3) 0.006(3) 0.007(3)
C123 0.018(3) 0.018(3) 0.020(3) 0.002(3) 0.000(2) -0.001(2)
C124 0.026(3) 0.032(3) 0.017(3) -0.002(3) -0.003(2) 0.000(3)
C125 0.021(3) 0.025(3) 0.025(3) 0.004(3) 0.003(3) 0.003(3)
C126 0.024(3) 0.034(3) 0.023(3) -0.003(3) 0.011(3) -0.001(3)
C127 0.032(3) 0.018(3) 0.021(3) -0.002(3) 0.005(2) -0.004(3)
C128 0.022(3) 0.015(3) 0.031(3) -0.001(3) 0.006(3) 0.000(2)
C129 0.022(3) 0.025(3) 0.023(3) 0.000(3) 0.009(3) -0.002(2)
C130 0.033(3) 0.032(4) 0.021(3) 0.003(3) 0.010(3) 0.001(3)
C131 0.042(4) 0.023(4) 0.050(4) 0.000(3) 0.024(3) 0.003(3)
C132 0.042(4) 0.035(4) 0.034(4) 0.008(3) 0.014(3) 0.003(3)
C133 0.045(4) 0.033(4) 0.028(3) 0.001(3) 0.011(3) -0.002(3)
C134 0.037(3) 0.030(3) 0.029(3) 0.004(3) 0.012(3) 0.007(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
B1 C1 1.619(7) . ?
B1 C5 1.590(7) . ?
B1 O1A 1.501(7) . ?
B1 O1B 1.282(9) . ?
N1 C1 1.298(5) . ?
N1 C4 1.563(5) . ?
N1 C8 1.490(5) . ?
N2 C7 1.335(6) . ?
N2 C21 1.507(5) . ?
N2 C23 1.476(5) . ?
N3 C6 1.316(5) . ?
N3 C26 1.491(5) . ?
N3 C29 1.484(5) . ?
C1 C2 1.535(5) . ?
C2 C3 1.534(5) . ?
C2 C14 1.560(5) . ?
C2 C16 1.535(5) . ?
C3 C4 1.535(5) . ?
C4 C18 1.520(6) . ?
C4 C19 1.512(6) . ?
C5 C6 1.386(6) . ?
C5 C7 1.381(6) . ?
C6 C7 1.387(6) . ?
C8 C9 1.397(5) . ?
C8 C13 1.402(5) . ?
C9 C10 1.403(5) . ?
C9 C32 1.523(6) . ?
C10 C11 1.379(6) . ?
C11 C12 1.380(5) . ?
C12 C13 1.392(5) . ?
C13 C35 1.529(6) . ?
C14 C15 1.523(5) . ?
C16 C17 1.526(5) . ?
C20 C21 1.487(5) . ?
C21 C22 1.296(6) . ?
C23 C24 1.528(5) . ?
C23 C25 1.526(5) . ?
C26 C27 1.532(5) . ?
C26 C28 1.524(5) . ?
C29 C30 1.518(5) . ?
C29 C31 1.526(5) . ?
C32 C33 1.549(5) . ?
C32 C34 1.536(5) . ?
C35 C36 1.547(5) . ?
C35 C37 1.537(5) . ?
S1A O1A 1.499(4) . ?
S1A O2A 1.454(4) . ?
S1A O3A 1.459(4) . ?
S1A C3A 1.825(9) . ?
C3A F1A 1.326(5) . ?
C3A F2A 1.330(5) . ?
C3A F3A 1.336(5) . ?
S1B O1B 1.486(4) . ?
S1B O2B 1.455(5) . ?
S1B O3B 1.463(5) . ?
S1B C3B 1.815(12) . ?
C3B F1B 1.328(5) . ?
C3B F2B 1.327(5) . ?
C3B F3B 1.333(5) . ?
B2 C111 1.633(6) . ?
B2 C117 1.637(6) . ?
B2 C123 1.660(6) . ?
B2 C129 1.642(6) . ?
C111 C112 1.398(5) . ?
C111 C116 1.407(6) . ?
C112 C113 1.405(6) . ?
C113 C114 1.386(6) . ?
C114 C115 1.377(6) . ?
C115 C116 1.387(6) . ?
C117 C118 1.408(5) . ?
C117 C122 1.398(5) . ?
C118 C119 1.388(5) . ?
C119 C120 1.380(5) . ?
C120 C121 1.385(5) . ?
C121 C122 1.404(5) . ?
C123 C124 1.402(5) . ?
C123 C128 1.395(5) . ?
C124 C125 1.396(5) . ?
C125 C126 1.386(5) . ?
C126 C127 1.380(5) . ?
C127 C128 1.411(5) . ?
C129 C130 1.409(5) . ?
C129 C134 1.402(5) . ?
C130 C131 1.391(6) . ?
C131 C132 1.383(6) . ?
C132 C133 1.371(6) . ?
C133 C134 1.394(6) . ?
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
C5 B1 C1 114.3(4) . . ?
O1A B1 C1 116.9(5) . . ?
O1A B1 C5 113.6(5) . . ?
O1B B1 C1 123.9(6) . . ?
O1B B1 C5 117.7(6) . . ?
O1B B1 O1A 57.3(5) . . ?
C1 N1 C4 115.0(3) . . ?
C1 N1 C8 126.3(3) . . ?
C8 N1 C4 118.6(3) . . ?
C7 N2 C21 117.5(4) . . ?
C7 N2 C23 119.0(4) . . ?
C23 N2 C21 123.0(4) . . ?
C6 N3 C26 117.5(4) . . ?
C6 N3 C29 122.6(4) . . ?
C29 N3 C26 119.1(4) . . ?
N1 C1 B1 126.7(4) . . ?
N1 C1 C2 109.5(4) . . ?
C2 C1 B1 123.7(4) . . ?
C1 C2 C14 108.5(3) . . ?
C1 C2 C16 111.5(3) . . ?
C3 C2 C1 103.0(3) . . ?
C3 C2 C14 112.3(3) . . ?
C3 C2 C16 112.1(4) . . ?
C16 C2 C14 109.3(4) . . ?
C2 C3 C4 107.5(3) . . ?
C3 C4 N1 98.3(3) . . ?
C18 C4 N1 109.5(3) . . ?
C18 C4 C3 112.9(4) . . ?
C19 C4 N1 113.4(3) . . ?
C19 C4 C3 113.8(4) . . ?
C19 C4 C18 108.6(4) . . ?
C6 C5 B1 146.0(5) . . ?
C7 C5 B1 152.8(5) . . ?
C7 C5 C6 60.2(3) . . ?
N3 C6 C5 147.6(5) . . ?
N3 C6 C7 152.7(5) . . ?
C5 C6 C7 59.7(3) . . ?
N2 C7 C5 149.7(5) . . ?
N2 C7 C6 150.1(5) . . ?
C5 C7 C6 60.1(3) . . ?
C9 C8 N1 119.8(4) . . ?
C9 C8 C13 123.1(4) . . ?
C13 C8 N1 117.1(4) . . ?
C8 C9 C10 116.7(4) . . ?
C8 C9 C32 125.4(4) . . ?
C10 C9 C32 117.9(4) . . ?
C11 C10 C9 121.7(4) . . ?
C10 C11 C12 119.7(4) . . ?
C11 C12 C13 121.7(4) . . ?
C8 C13 C35 125.1(4) . . ?
C12 C13 C8 117.1(4) . . ?
C12 C13 C35 117.8(4) . . ?
C15 C14 C2 115.4(3) . . ?
C17 C16 C2 116.0(4) . . ?
C20 C21 N2 110.0(4) . . ?
C22 C21 N2 120.8(4) . . ?
C22 C21 C20 128.4(5) . . ?
N2 C23 C24 111.0(4) . . ?
N2 C23 C25 114.1(4) . . ?
C25 C23 C24 110.9(4) . . ?
N3 C26 C27 109.6(4) . . ?
N3 C26 C28 111.9(3) . . ?
C28 C26 C27 112.3(4) . . ?
N3 C29 C30 110.2(4) . . ?
N3 C29 C31 112.3(3) . . ?
C30 C29 C31 114.3(4) . . ?
C9 C32 C33 111.4(4) . . ?
C9 C32 C34 111.5(3) . . ?
C34 C32 C33 108.1(4) . . ?
C13 C35 C36 111.0(4) . . ?
C13 C35 C37 112.0(3) . . ?
C37 C35 C36 108.8(4) . . ?
O1A S1A C3A 104.5(3) . . ?
O2A S1A O1A 112.7(3) . . ?
O2A S1A O3A 118.7(3) . . ?
O2A S1A C3A 104.5(4) . . ?
O3A S1A O1A 110.5(3) . . ?
O3A S1A C3A 104.3(4) . . ?
S1A O1A B1 125.2(4) . . ?
F1A C3A S1A 111.8(7) . . ?
F1A C3A F2A 109.7(7) . . ?
F1A C3A F3A 107.4(6) . . ?
F2A C3A S1A 110.0(5) . . ?
F2A C3A F3A 108.1(6) . . ?
F3A C3A S1A 109.8(7) . . ?
O1B S1B C3B 100.9(5) . . ?
O2B S1B O1B 114.7(5) . . ?
O2B S1B O3B 118.8(5) . . ?
O2B S1B C3B 102.6(8) . . ?
O3B S1B O1B 112.7(5) . . ?
O3B S1B C3B 104.1(7) . . ?
B1 O1B S1B 135.3(7) . . ?
F1B C3B S1B 110.7(8) . . ?
F1B C3B F3B 108.9(7) . . ?
F2B C3B S1B 109.9(8) . . ?
F2B C3B F1B 110.5(7) . . ?
F2B C3B F3B 107.9(6) . . ?
F3B C3B S1B 108.8(9) . . ?
C111 B2 C117 109.5(4) . . ?
C111 B2 C123 106.6(4) . . ?
C111 B2 C129 111.3(4) . . ?
C117 B2 C123 111.8(4) . . ?
C117 B2 C129 109.8(4) . . ?
C129 B2 C123 107.9(4) . . ?
C112 C111 B2 123.7(4) . . ?
C112 C111 C116 114.5(4) . . ?
C116 C111 B2 121.4(4) . . ?
C111 C112 C113 122.5(5) . . ?
C114 C113 C112 120.3(5) . . ?
C115 C114 C113 118.8(5) . . ?
C114 C115 C116 120.0(5) . . ?
C115 C116 C111 123.7(5) . . ?
C118 C117 B2 120.4(4) . . ?
C122 C117 B2 125.3(4) . . ?
C122 C117 C118 114.3(4) . . ?
C119 C118 C117 122.8(4) . . ?
C120 C119 C118 121.3(4) . . ?
C119 C120 C121 118.2(4) . . ?
C120 C121 C122 119.8(4) . . ?
C117 C122 C121 123.6(4) . . ?
C124 C123 B2 121.4(4) . . ?
C128 C123 B2 124.2(4) . . ?
C128 C123 C124 114.4(4) . . ?
C125 C124 C123 123.6(4) . . ?
C126 C125 C124 119.8(4) . . ?
C127 C126 C125 119.2(4) . . ?
C126 C127 C128 119.6(4) . . ?
C123 C128 C127 123.4(4) . . ?
C130 C129 B2 121.7(4) . . ?
C134 C129 B2 124.4(4) . . ?
C134 C129 C130 113.9(4) . . ?
C131 C130 C129 123.1(4) . . ?
C132 C131 C130 120.5(5) . . ?
C133 C132 C131 118.5(5) . . ?
C132 C133 C134 120.6(5) . . ?
C133 C134 C129 123.4(4) . . ?
_database_code_depnum_ccdc_archive 'CCDC 1001685'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_gb_mm1
_audit_creation_date 2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number 2013-2
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C36 H54 B F3 N3 O3 S, C24 H20 B'
_chemical_formula_sum 'C60 H74 B2 F3 N3 O3 S'
_chemical_formula_weight 995.90
_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'
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'
S S 0.1246 0.1234 '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 14.2524(5)
_cell_length_b 13.4771(5)
_cell_length_c 28.1965(9)
_cell_angle_alpha 90
_cell_angle_beta 91.7220(10)
_cell_angle_gamma 90
_cell_volume 5413.6(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9895
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 26.38
_cell_measurement_theta_min 2.56
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.118
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type ?
_exptl_absorpt_process_details ?
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.222
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description ?
_exptl_crystal_F_000 2128
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.18
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0671
_diffrn_reflns_av_unetI/netI 0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_number 34655
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.390
_diffrn_reflns_theta_min 2.509
_diffrn_ambient_temperature 100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 8741
_reflns_number_total 10835
_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 ?
_computing_data_collection ?
_computing_data_reduction ?
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.556
_refine_diff_density_min -0.492
_refine_diff_density_rms 0.076
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.021
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 661
_refine_ls_number_reflns 10835
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0620
_refine_ls_R_factor_gt 0.0479
_refine_ls_restrained_S_all 1.021
_refine_ls_shift/su_max 0.015
_refine_ls_shift/su_mean 0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+2.1800P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1248
_refine_ls_wR_factor_ref 0.1350
_refine_special_details
;
?
;
_olex2_refinement_description
;
1. Others
Fixed Uiso: H12(0.018) H13(0.019) H15(0.016) H17(0.02) H21(0.019) H22(0.02)
H24A(0.027) H24B(0.027) H24C(0.027) H25(0.02) H26A(0.027) H26B(0.027)
H26C(0.027) H28A(0.022) H28B(0.022) H28C(0.022) H29(0.02) H30(0.026)
H31(0.016) H32A(0.019) H32B(0.019) H33(0.018) H36(0.022) H37(0.022) H38(0.02)
H39(0.025) H40(0.02) H42A(0.026) H42B(0.026) H42C(0.026) H43A(0.038)
H43B(0.038) H43C(0.038) H44A(0.029) H44B(0.029) H44C(0.029) H45(0.019)
H47A(0.026) H47B(0.026) H47C(0.026) H48(0.023) H49(0.022) H51A(0.022)
H51B(0.022) H52(0.021) H53A(0.021) H53B(0.021) H54(0.023) H55(0.025) H56(0.03)
H58(0.019) H59A(0.028) H59B(0.028) H59C(0.028) H60(0.017) H61(0.036)
H62(0.032) H63(0.041) H64(0.025) H65A(0.031) H65B(0.031) H65C(0.031)
H66(0.039) H67A(0.035) H67B(0.035) H67C(0.035) H68(0.036) H69A(0.044)
H69B(0.044) H69C(0.044) H70A(0.037) H70B(0.037) H70C(0.037) H71(0.037)
Fixed X: H12(-0.3248) H13(0.2593) H15(0.4983) H17(-0.4037) H21(0.4954) H22(-
0.5316) H24A(0.1411) H24B(0.2165) H24C(0.1282) H25(0.388) H26A(0.2293)
H26B(0.3225) H26C(0.3028) H28A(0.5014) H28B(0.5342) H28C(0.5449) H29(-0.392)
H30(-0.21) H31(0.2757) H32A(0.4727) H32B(0.4081) H33(0.2006) H36(-0.2523) H37(-
0.5437) H38(0.1054) H39(-0.2615) H40(-0.61) H42A(0.4922) H42B(0.5314)
H42C(0.4242) H43A(0.0535) H43B(0.0253) H43C(-0.0476) H44A(0.1132) H44B(0.0577)
H44C(0.1102) H45(0.0753) H47A(0.6149) H47B(0.6487) H47C(0.6153) H48(-0.2138)
H49(-0.1588) H51A(0.3048) H51B(0.3672) H52(-0.0731) H53A(0.1965) H53B(0.2134)
H54(-0.3194) H55(-0.4194) H56(-0.0896) H58(-0.098) H59A(0.2907) H59B(0.3833)
H59C(0.3503) H60(0.2992) H61(0.0255) H62(-0.1225) H63(-0.2952) H64(-0.15)
H65A(0.2028) H65B(0.1413) H65C(0.2511) H66(0.0406) H67A(-0.0769) H67B(-0.0445)
H67C(0.0002) H68(-0.1571) H69A(0.2864) H69B(0.1943) H69C(0.2911) H70A(0.4373)
H70B(0.4991) H70C(0.452) H71(-0.4267)
Fixed Y: H12(0.829) H13(0.4335) H15(0.6792) H17(0.6112) H21(0.5914)
H22(0.7945) H24A(1.0223) H24B(1.1043) H24C(1.0944) H25(0.4859) H26A(1.0731)
H26B(1.0802) H26C(0.9866) H28A(0.4701) H28B(0.4517) H28C(0.5572) H29(0.8428)
H30(0.5091) H31(0.9552) H32A(0.6312) H32B(0.5578) H33(0.4848) H36(0.7199)
H37(0.5634) H38(0.6287) H39(0.5886) H40(0.6545) H42A(0.7804) H42B(0.8268)
H42C(0.8023) H43A(0.6233) H43B(0.5351) H43C(0.6188) H44A(0.5716) H44B(0.4783)
H44C(0.4751) H45(1.0704) H47A(0.578) H47B(0.6875) H47C(0.6528) H48(0.59)
H49(0.9155) H51A(0.8164) H51B(0.7671) H52(1.061) H53A(0.6875) H53B(0.5799)
H54(0.7497) H55(0.905) H56(0.7529) H58(0.7719) H59A(0.4492) H59B(0.3943)
H59C(0.3934) H60(0.8103) H61(0.674) H62(0.6777) H63(1.172) H64(0.9282)
H65A(0.3248) H65B(0.3252) H65C(0.3226) H66(0.7134) H67A(0.7073) H67B(0.6049)
H67C(0.7036) H68(1.0977) H69A(0.5339) H69B(0.5889) H69C(0.644) H70A(0.8287)
H70B(0.7832) H70C(0.8873) H71(1.0744)
Fixed Z: H12(0.4089) H13(0.1777) H15(0.2914) H17(0.4855) H21(0.1734)
H22(0.606) H24A(0.2724) H24B(0.2838) H24C(0.3153) H25(0.1371) H26A(0.3896)
H26B(0.3616) H26C(0.3927) H28A(0.3004) H28B(0.3533) H28C(0.3306) H29(0.5739)
H30(0.4011) H31(0.3113) H32A(0.392) H32B(0.4197) H33(0.2958) H36(0.5986)
H37(0.5166) H38(0.3189) H39(0.3317) H40(0.5769) H42A(0.2031) H42B(0.2507)
H42C(0.2445) H43A(0.4024) H43B(0.3687) H43C(0.3791) H44A(0.2356) H44B(0.2525)
H44C(0.2045) H45(0.388) H47A(0.2554) H47B(0.2637) H47C(0.2129) H48(0.4728)
H49(0.4162) H51A(0.3986) H51B(0.4385) H52(0.4194) H53A(0.4094) H53B(0.3908)
H54(0.3367) H55(0.4764) H56(0.4868) H58(0.384) H59A(0.3651) H59B(0.3812)
H59C(0.3276) H60(0.3016) H61(0.6126) H62(0.6447) H63(0.4802) H64(0.5183)
H65A(0.2301) H65B(0.2753) H65C(0.2808) H66(0.5329) H67A(0.304) H67B(0.2838)
H67C(0.2655) H68(0.5073) H69A(0.4608) H69B(0.4746) H69C(0.4786) H70A(0.3509)
H70B(0.3924) H70C(0.3986) H71(0.4654)
;
_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
N5 N 0.16141(9) 0.90548(10) 0.34455(5) 0.0116(3) Uani 1 1 d . . . . .
N7 N 0.35289(9) 0.59251(9) 0.31175(5) 0.0107(3) Uani 1 1 d . . . . .
C9 C -0.27009(11) 0.72035(12) 0.45023(6) 0.0140(3) Uani 1 1 d . . . . .
N10 N 0.08282(9) 0.76595(10) 0.34462(5) 0.0124(3) Uani 1 1 d . . . . .
C11 C 0.43322(11) 0.60246(11) 0.23640(6) 0.0126(3) Uani 1 1 d . . . . .
C12 C -0.30112(11) 0.76474(12) 0.40788(6) 0.0149(3) Uani 1 1 d . . . . .
H12 H -0.3248 0.8290 0.4089 0.018 Uiso 1 1 calc R . . . .
C13 C 0.30307(12) 0.47466(12) 0.19284(6) 0.0156(3) Uani 1 1 d . . . . .
H13 H 0.2593 0.4335 0.1777 0.019 Uiso 1 1 calc R . . . .
C14 C 0.28923(11) 0.50217(12) 0.23988(6) 0.0129(3) Uani 1 1 d . . . . .
C15 C 0.50453(11) 0.67693(12) 0.25689(6) 0.0137(3) Uani 1 1 d . . . . .
H15 H 0.4983 0.6792 0.2914 0.016 Uiso 1 1 calc R . . . .
C16 C 0.07689(11) 0.92504(12) 0.36674(6) 0.0127(3) Uani 1 1 d . . . . .
C17 C -0.42867(11) 0.64922(12) 0.50955(6) 0.0165(3) Uani 1 1 d . . . . .
H17 H -0.4037 0.6112 0.4855 0.020 Uiso 1 1 calc R . . . .
C18 C 0.35593(11) 0.56652(11) 0.26129(6) 0.0113(3) Uani 1 1 d . . . . .
C19 C -0.37907(11) 0.73388(12) 0.52532(6) 0.0137(3) Uani 1 1 d . . . . .
C20 C -0.18838(12) 0.74021(12) 0.53655(6) 0.0157(3) Uani 1 1 d . . . . .
C21 C 0.44387(11) 0.56998(12) 0.19004(6) 0.0155(3) Uani 1 1 d . . . . .
H21 H 0.4954 0.5914 0.1734 0.019 Uiso 1 1 calc R . . . .
C22 C -0.50650(12) 0.75762(13) 0.58157(6) 0.0167(3) Uani 1 1 d . . . . .
H22 H -0.5316 0.7945 0.6060 0.020 Uiso 1 1 calc R . . . .
C23 C 0.02642(11) 0.83655(12) 0.36624(6) 0.0131(3) Uani 1 1 d . . . . .
C24 C 0.17314(12) 1.05852(13) 0.29731(6) 0.0177(4) Uani 1 1 d . . . . .
H24A H 0.1411 1.0223 0.2724 0.027 Uiso 1 1 calc GR . . . .
H24B H 0.2165 1.1043 0.2838 0.027 Uiso 1 1 calc GR . . . .
H24C H 0.1282 1.0944 0.3153 0.027 Uiso 1 1 calc GR . . . .
C25 C 0.37973(12) 0.50668(12) 0.16811(6) 0.0169(3) Uani 1 1 d . . . . .
H25 H 0.3880 0.4859 0.1371 0.020 Uiso 1 1 calc R . . . .
C26 C 0.27477(12) 1.03608(13) 0.37235(6) 0.0177(4) Uani 1 1 d . . . . .
H26A H 0.2293 1.0731 0.3896 0.027 Uiso 1 1 calc GR . . . .
H26B H 0.3225 1.0802 0.3616 0.027 Uiso 1 1 calc GR . . . .
H26C H 0.3028 0.9866 0.3927 0.027 Uiso 1 1 calc GR . . . .
C27 C -0.28309(12) 0.89420(12) 0.49788(6) 0.0157(3) Uani 1 1 d . . . . .
C28 C 0.50637(11) 0.49889(12) 0.33153(6) 0.0150(3) Uani 1 1 d . . . . .
H28A H 0.5014 0.4701 0.3004 0.022 Uiso 1 1 calc GR . . . .
H28B H 0.5342 0.4517 0.3533 0.022 Uiso 1 1 calc GR . . . .
H28C H 0.5449 0.5572 0.3306 0.022 Uiso 1 1 calc GR . . . .
C29 C -0.42173(12) 0.78620(12) 0.56200(6) 0.0163(3) Uani 1 1 d . . . . .
H29 H -0.3920 0.8428 0.5739 0.020 Uiso 1 1 calc R . . . .
C30 C -0.23277(12) 0.57375(13) 0.40231(7) 0.0215(4) Uani 1 1 d . . . . .
H30 H -0.2100 0.5091 0.4011 0.026 Uiso 1 1 calc R . . . .
C31 C 0.22671(11) 0.98603(12) 0.32994(6) 0.0136(3) Uani 1 1 d . . . . .
H31 H 0.2757 0.9552 0.3113 0.016 Uiso 1 1 calc R . . . .
C32 C 0.41347(11) 0.59562(13) 0.39067(6) 0.0156(3) Uani 1 1 d . . . . .
H32A H 0.4727 0.6312 0.3920 0.019 Uiso 1 1 calc R . . . .
H32B H 0.4081 0.5578 0.4197 0.019 Uiso 1 1 calc R . . . .
C33 C 0.20128(11) 0.46204(12) 0.26276(6) 0.0152(3) Uani 1 1 d . . . . .
H33 H 0.2006 0.4848 0.2958 0.018 Uiso 1 1 calc R . . . .
C34 C 0.40911(11) 0.52675(12) 0.34782(6) 0.0129(3) Uani 1 1 d . . . . .
C35 C 0.16457(11) 0.80846(12) 0.33188(6) 0.0118(3) Uani 1 1 d . . . . .
C36 C -0.19396(12) 0.71800(13) 0.58475(6) 0.0183(4) Uani 1 1 d . . . . .
H36 H -0.2523 0.7199 0.5986 0.022 Uiso 1 1 calc R . . . .
C37 C -0.51346(12) 0.61978(13) 0.52835(6) 0.0183(4) Uani 1 1 d . . . . .
H37 H -0.5437 0.5634 0.5166 0.022 Uiso 1 1 calc R . . . .
C38 C 0.05162(11) 0.66399(12) 0.33176(6) 0.0171(4) Uani 1 1 d . . . . .
H38 H 0.1054 0.6287 0.3189 0.020 Uiso 1 1 calc R . . . .
C39 C -0.26377(12) 0.62077(14) 0.36085(7) 0.0211(4) Uani 1 1 d . . . . .
H39 H -0.2615 0.5886 0.3317 0.025 Uiso 1 1 calc R . . . .
C40 C -0.55319(11) 0.67385(13) 0.56443(6) 0.0169(4) Uani 1 1 d . . . . .
H40 H -0.6100 0.6545 0.5769 0.020 Uiso 1 1 calc R . . . .
C41 C 0.30927(10) 0.66686(12) 0.33109(6) 0.0116(3) Uani 1 1 d . . . . .
C42 C 0.48640(12) 0.78136(12) 0.23693(6) 0.0176(4) Uani 1 1 d . . . . .
H42A H 0.4922 0.7804 0.2031 0.026 Uiso 1 1 calc GR . . . .
H42B H 0.5314 0.8268 0.2507 0.026 Uiso 1 1 calc GR . . . .
H42C H 0.4242 0.8023 0.2445 0.026 Uiso 1 1 calc GR . . . .
C43 C 0.01749(12) 0.60474(14) 0.37450(7) 0.0251(4) Uani 1 1 d . . . . .
H43A H 0.0535 0.6233 0.4024 0.038 Uiso 1 1 calc GR . . . .
H43B H 0.0253 0.5351 0.3687 0.038 Uiso 1 1 calc GR . . . .
H43C H -0.0476 0.6188 0.3791 0.038 Uiso 1 1 calc GR . . . .
C44 C 0.11220(11) 0.50039(14) 0.23634(6) 0.0196(4) Uani 1 1 d . . . . .
H44A H 0.1132 0.5716 0.2356 0.029 Uiso 1 1 calc GR . . . .
H44B H 0.0577 0.4783 0.2525 0.029 Uiso 1 1 calc GR . . . .
H44C H 0.1102 0.4751 0.2045 0.029 Uiso 1 1 calc GR . . . .
C45 C 0.04118(11) 1.01156(12) 0.38705(6) 0.0158(3) Uani 1 1 d . . . . .
H45 H 0.0753 1.0704 0.3880 0.019 Uiso 1 1 calc R . . . .
C47 C 0.60530(11) 0.64592(13) 0.24621(6) 0.0172(4) Uani 1 1 d . . . . .
H47A H 0.6149 0.5780 0.2554 0.026 Uiso 1 1 calc GR . . . .
H47B H 0.6487 0.6875 0.2637 0.026 Uiso 1 1 calc GR . . . .
H47C H 0.6153 0.6528 0.2129 0.026 Uiso 1 1 calc GR . . . .
C48 C -0.23560(12) 0.62293(13) 0.44569(6) 0.0190(4) Uani 1 1 d . . . . .
H48 H -0.2138 0.5900 0.4728 0.023 Uiso 1 1 calc R . . . .
C49 C -0.09895(12) 0.91639(13) 0.40390(6) 0.0180(4) Uani 1 1 d . . . . .
H49 H -0.1588 0.9155 0.4162 0.022 Uiso 1 1 calc R . . . .
B50 B -0.27951(13) 0.77212(14) 0.50283(7) 0.0139(4) Uani 1 1 d . . . . .
C51 C 0.35795(12) 0.77259(13) 0.40437(6) 0.0179(4) Uani 1 1 d . . . . .
H51A H 0.3048 0.8164 0.3986 0.022 Uiso 1 1 calc R . . . .
H51B H 0.3672 0.7671 0.4385 0.022 Uiso 1 1 calc R . . . .
C52 C -0.04714(12) 1.00520(13) 0.40553(6) 0.0176(4) Uani 1 1 d . . . . .
H52 H -0.0731 1.0610 0.4194 0.021 Uiso 1 1 calc R . . . .
C53 C 0.24112(12) 0.63319(14) 0.40961(6) 0.0179(4) Uani 1 1 d . . . . .
H53A H 0.1965 0.6875 0.4094 0.021 Uiso 1 1 calc R . . . .
H53B H 0.2134 0.5799 0.3908 0.021 Uiso 1 1 calc R . . . .
C54 C -0.29820(12) 0.71697(13) 0.36399(6) 0.0191(4) Uani 1 1 d . . . . .
H54 H -0.3194 0.7497 0.3367 0.023 Uiso 1 1 calc R . . . .
C55 C -0.36573(13) 0.94278(13) 0.48247(6) 0.0210(4) Uani 1 1 d . . . . .
H55 H -0.4194 0.9050 0.4764 0.025 Uiso 1 1 calc R . . . .
C56 C -0.09722(13) 0.73779(15) 0.51860(7) 0.0251(4) Uani 1 1 d . . . . .
H56 H -0.0896 0.7529 0.4868 0.030 Uiso 1 1 calc R . . . .
C57 C 0.33119(11) 0.66891(12) 0.38495(6) 0.0137(3) Uani 1 1 d . . . . .
C58 C -0.06374(11) 0.83070(13) 0.38472(6) 0.0156(3) Uani 1 1 d . . . . .
H58 H -0.0980 0.7719 0.3840 0.019 Uiso 1 1 calc R . . . .
C59 C 0.35318(11) 0.43215(13) 0.35621(7) 0.0188(4) Uani 1 1 d . . . . .
H59A H 0.2907 0.4492 0.3651 0.028 Uiso 1 1 calc GR . . . .
H59B H 0.3833 0.3943 0.3812 0.028 Uiso 1 1 calc GR . . . .
H59C H 0.3503 0.3934 0.3276 0.028 Uiso 1 1 calc GR . . . .
B60 B 0.25286(13) 0.75723(14) 0.30469(6) 0.0138(4) Uani 1 1 d . . . . .
H60 H 0.2992 0.8103 0.3016 0.017 Uiso 1 1 calc R . . . .
C61 C -0.02697(13) 0.69074(16) 0.59386(8) 0.0302(5) Uani 1 1 d . . . . .
H61 H 0.0255 0.6740 0.6126 0.036 Uiso 1 1 calc R . . . .
C62 C -0.11543(13) 0.69302(15) 0.61284(7) 0.0264(4) Uani 1 1 d . . . . .
H62 H -0.1225 0.6777 0.6447 0.032 Uiso 1 1 calc R . . . .
C63 C -0.29246(16) 1.10374(14) 0.48482(7) 0.0338(5) Uani 1 1 d . . . . .
H63 H -0.2952 1.1720 0.4802 0.041 Uiso 1 1 calc R . . . .
C64 C -0.20613(13) 0.95636(13) 0.50728(6) 0.0208(4) Uani 1 1 d . . . . .
H64 H -0.1500 0.9282 0.5183 0.025 Uiso 1 1 calc R . . . .
C65 C 0.19890(13) 0.34796(13) 0.26216(7) 0.0205(4) Uani 1 1 d . . . . .
H65A H 0.2028 0.3248 0.2301 0.031 Uiso 1 1 calc GR . . . .
H65B H 0.1413 0.3252 0.2753 0.031 Uiso 1 1 calc GR . . . .
H65C H 0.2511 0.3226 0.2808 0.031 Uiso 1 1 calc GR . . . .
C66 C -0.01825(13) 0.71387(17) 0.54631(8) 0.0322(5) Uani 1 1 d . . . . .
H66 H 0.0406 0.7134 0.5329 0.039 Uiso 1 1 calc R . . . .
C67 C -0.02446(12) 0.67056(14) 0.29266(7) 0.0237(4) Uani 1 1 d . . . . .
H67A H -0.0769 0.7073 0.3040 0.035 Uiso 1 1 calc GR . . . .
H67B H -0.0445 0.6049 0.2838 0.035 Uiso 1 1 calc GR . . . .
H67C H 0.0002 0.7036 0.2655 0.035 Uiso 1 1 calc GR . . . .
C68 C -0.21013(16) 1.05915(15) 0.50080(7) 0.0303(5) Uani 1 1 d . . . . .
H68 H -0.1571 1.0977 0.5073 0.036 Uiso 1 1 calc R . . . .
C69 C 0.25445(14) 0.59662(17) 0.46062(7) 0.0291(5) Uani 1 1 d . . . . .
H69A H 0.2864 0.5339 0.4608 0.044 Uiso 1 1 calc GR . . . .
H69B H 0.1943 0.5889 0.4746 0.044 Uiso 1 1 calc GR . . . .
H69C H 0.2911 0.6440 0.4786 0.044 Uiso 1 1 calc GR . . . .
C70 C 0.44461(12) 0.82258(14) 0.38474(7) 0.0249(4) Uani 1 1 d . . . . .
H70A H 0.4373 0.8287 0.3509 0.037 Uiso 1 1 calc GR . . . .
H70B H 0.4991 0.7832 0.3924 0.037 Uiso 1 1 calc GR . . . .
H70C H 0.4520 0.8873 0.3986 0.037 Uiso 1 1 calc GR . . . .
C71 C -0.37068(15) 1.04534(14) 0.47585(7) 0.0306(5) Uani 1 1 d . . . . .
H71 H -0.4267 1.0744 0.4654 0.037 Uiso 1 1 calc R . . . .
S1 S 0.19409(3) 0.81478(3) 0.21851(2) 0.01787(12) Uani 1 1 d . . . . .
O5 O 0.22051(8) 0.73164(8) 0.25352(4) 0.0164(3) Uani 1 1 d . . . . .
F1 F 0.20166(7) 0.81507(8) 0.12747(4) 0.0246(2) Uani 1 1 d . . . . .
F2 F 0.31226(7) 0.73156(9) 0.16202(4) 0.0285(3) Uani 1 1 d . . . . .
F3 F 0.17258(9) 0.67084(8) 0.15652(4) 0.0328(3) Uani 1 1 d . . . . .
C3 C 0.22220(12) 0.75292(13) 0.16286(6) 0.0189(4) Uani 1 1 d . . . . .
O1 O 0.25618(10) 0.89755(9) 0.22211(5) 0.0260(3) Uani 1 1 d . . . . .
O2 O 0.09557(9) 0.83129(11) 0.21683(5) 0.0300(3) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.0111(6) 0.0124(7) 0.0114(7) -0.0012(5) 0.0012(5) -0.0003(5)
N7 0.0103(6) 0.0104(6) 0.0113(7) 0.0015(5) -0.0009(5) -0.0015(5)
C9 0.0103(7) 0.0162(8) 0.0157(8) -0.0011(6) 0.0020(6) -0.0022(6)
N10 0.0115(6) 0.0131(7) 0.0126(7) 0.0003(5) -0.0008(5) 0.0003(5)
C11 0.0130(7) 0.0109(7) 0.0138(8) 0.0008(6) -0.0006(6) 0.0022(6)
C12 0.0115(7) 0.0151(8) 0.0182(9) -0.0004(7) 0.0014(6) -0.0014(6)
C13 0.0163(8) 0.0145(8) 0.0159(9) -0.0034(6) -0.0027(7) -0.0002(6)
C14 0.0134(8) 0.0108(8) 0.0146(8) 0.0004(6) -0.0005(6) 0.0024(6)
C15 0.0138(8) 0.0165(8) 0.0111(8) -0.0001(6) 0.0023(6) -0.0021(6)
C16 0.0119(7) 0.0170(8) 0.0091(7) 0.0012(6) -0.0001(6) 0.0006(6)
C17 0.0174(8) 0.0161(8) 0.0160(8) -0.0010(7) 0.0015(7) 0.0014(6)
C18 0.0130(7) 0.0103(7) 0.0107(8) 0.0002(6) 0.0001(6) 0.0034(6)
C19 0.0145(8) 0.0146(8) 0.0119(8) 0.0025(6) -0.0044(6) 0.0017(6)
C20 0.0168(8) 0.0129(8) 0.0172(9) 0.0010(6) -0.0018(7) -0.0022(6)
C21 0.0150(8) 0.0175(8) 0.0141(8) 0.0019(7) 0.0021(6) 0.0003(6)
C22 0.0180(8) 0.0193(9) 0.0127(8) 0.0004(7) 0.0015(7) 0.0041(7)
C23 0.0137(8) 0.0151(8) 0.0104(8) -0.0002(6) -0.0008(6) 0.0025(6)
C24 0.0183(8) 0.0173(8) 0.0176(9) 0.0031(7) 0.0013(7) -0.0006(7)
C25 0.0205(8) 0.0187(8) 0.0114(8) -0.0023(7) -0.0005(7) 0.0021(7)
C26 0.0186(8) 0.0168(8) 0.0177(9) -0.0028(7) -0.0003(7) -0.0025(7)
C27 0.0223(8) 0.0159(8) 0.0091(8) -0.0006(6) 0.0057(7) -0.0009(7)
C28 0.0145(8) 0.0143(8) 0.0161(8) 0.0012(6) -0.0002(6) 0.0021(6)
C29 0.0189(8) 0.0162(8) 0.0137(8) -0.0012(7) -0.0031(7) -0.0023(7)
C30 0.0196(9) 0.0175(9) 0.0276(10) -0.0049(7) 0.0042(7) 0.0002(7)
C31 0.0131(7) 0.0128(8) 0.0149(8) -0.0002(6) 0.0032(6) -0.0020(6)
C32 0.0138(8) 0.0201(9) 0.0127(8) -0.0003(7) -0.0029(6) 0.0037(7)
C33 0.0144(8) 0.0162(8) 0.0150(8) -0.0038(6) 0.0002(6) -0.0023(6)
C34 0.0131(8) 0.0133(8) 0.0120(8) 0.0035(6) -0.0022(6) 0.0006(6)
C35 0.0113(7) 0.0133(8) 0.0106(8) 0.0005(6) -0.0024(6) 0.0004(6)
C36 0.0179(8) 0.0181(9) 0.0187(9) 0.0023(7) -0.0012(7) -0.0032(7)
C37 0.0176(8) 0.0155(8) 0.0216(9) -0.0017(7) -0.0017(7) -0.0023(7)
C38 0.0135(8) 0.0117(8) 0.0259(10) -0.0035(7) -0.0005(7) -0.0002(6)
C39 0.0176(8) 0.0260(9) 0.0201(9) -0.0089(7) 0.0053(7) -0.0060(7)
C40 0.0127(8) 0.0201(9) 0.0178(9) 0.0049(7) 0.0005(6) -0.0002(7)
C41 0.0090(7) 0.0134(8) 0.0125(8) -0.0002(6) 0.0010(6) -0.0031(6)
C42 0.0187(8) 0.0155(8) 0.0186(9) 0.0017(7) 0.0019(7) -0.0025(7)
C43 0.0163(9) 0.0176(9) 0.0414(12) 0.0084(8) 0.0010(8) -0.0022(7)
C44 0.0133(8) 0.0250(9) 0.0203(9) -0.0058(7) -0.0006(7) -0.0011(7)
C45 0.0177(8) 0.0145(8) 0.0153(9) -0.0010(6) 0.0010(7) -0.0004(6)
C47 0.0139(8) 0.0232(9) 0.0145(8) -0.0020(7) 0.0011(6) -0.0013(7)
C48 0.0188(8) 0.0181(9) 0.0204(9) 0.0031(7) 0.0022(7) 0.0018(7)
C49 0.0130(8) 0.0261(9) 0.0151(8) 0.0004(7) 0.0023(6) 0.0007(7)
B50 0.0157(9) 0.0138(9) 0.0122(9) 0.0010(7) 0.0005(7) -0.0011(7)
C51 0.0170(8) 0.0219(9) 0.0146(9) -0.0060(7) -0.0038(7) 0.0033(7)
C52 0.0181(8) 0.0204(9) 0.0144(8) -0.0025(7) 0.0029(7) 0.0040(7)
C53 0.0160(8) 0.0234(9) 0.0143(9) 0.0035(7) 0.0008(7) 0.0034(7)
C54 0.0164(8) 0.0257(9) 0.0152(9) 0.0001(7) -0.0008(7) -0.0050(7)
C55 0.0261(9) 0.0190(9) 0.0182(9) 0.0010(7) 0.0035(7) 0.0038(7)
C56 0.0195(9) 0.0354(11) 0.0205(10) 0.0064(8) 0.0012(7) 0.0000(8)
C57 0.0129(8) 0.0185(8) 0.0095(8) -0.0007(6) -0.0013(6) 0.0022(6)
C58 0.0134(8) 0.0190(8) 0.0143(8) 0.0015(7) 0.0009(6) -0.0020(6)
C59 0.0153(8) 0.0179(9) 0.0230(9) 0.0083(7) -0.0031(7) -0.0035(7)
B60 0.0140(8) 0.0153(9) 0.0120(9) 0.0006(7) -0.0012(7) 0.0007(7)
C61 0.0199(9) 0.0367(11) 0.0334(11) 0.0081(9) -0.0119(8) -0.0013(8)
C62 0.0278(10) 0.0333(11) 0.0179(9) 0.0086(8) -0.0054(8) -0.0025(8)
C63 0.0612(15) 0.0138(9) 0.0277(11) -0.0004(8) 0.0214(10) 0.0031(9)
C64 0.0278(9) 0.0228(9) 0.0122(8) -0.0037(7) 0.0053(7) -0.0051(7)
C65 0.0235(9) 0.0164(9) 0.0216(9) -0.0031(7) 0.0011(7) -0.0059(7)
C66 0.0145(9) 0.0469(13) 0.0352(12) 0.0055(10) -0.0002(8) -0.0003(8)
C67 0.0157(8) 0.0247(10) 0.0303(11) -0.0103(8) -0.0045(7) 0.0000(7)
C68 0.0477(12) 0.0228(10) 0.0214(10) -0.0078(8) 0.0158(9) -0.0146(9)
C69 0.0255(10) 0.0438(12) 0.0182(10) 0.0113(9) 0.0030(8) 0.0042(9)
C70 0.0172(9) 0.0250(10) 0.0323(11) -0.0069(8) -0.0044(8) -0.0016(7)
C71 0.0433(12) 0.0210(10) 0.0281(11) 0.0063(8) 0.0120(9) 0.0124(9)
S1 0.0223(2) 0.0188(2) 0.0124(2) 0.00178(16) -0.00037(16) 0.00687(17)
O5 0.0203(6) 0.0164(6) 0.0122(6) -0.0006(5) -0.0021(5) 0.0037(5)
F1 0.0283(6) 0.0303(6) 0.0149(5) 0.0064(4) -0.0020(4) 0.0044(5)
F2 0.0243(6) 0.0418(7) 0.0196(6) 0.0013(5) 0.0028(4) 0.0139(5)
F3 0.0496(7) 0.0271(6) 0.0216(6) -0.0028(5) -0.0014(5) -0.0110(5)
C3 0.0210(9) 0.0206(9) 0.0152(9) 0.0031(7) -0.0007(7) 0.0027(7)
O1 0.0397(8) 0.0182(6) 0.0197(7) 0.0015(5) -0.0055(6) 0.0013(6)
O2 0.0254(7) 0.0394(8) 0.0252(7) 0.0079(6) 0.0035(6) 0.0148(6)
_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
N5 C16 1.399(2) . ?
N5 C31 1.496(2) . ?
N5 C35 1.357(2) . ?
N7 C18 1.467(2) . ?
N7 C34 1.553(2) . ?
N7 C41 1.307(2) . ?
C9 C12 1.395(2) . ?
C9 C48 1.409(2) . ?
C9 B50 1.648(2) . ?
N10 C23 1.397(2) . ?
N10 C35 1.356(2) . ?
N10 C38 1.486(2) . ?
C11 C15 1.529(2) . ?
C11 C18 1.410(2) . ?
C11 C21 1.391(2) . ?
C12 C54 1.397(2) . ?
C13 C14 1.397(2) . ?
C13 C25 1.383(2) . ?
C14 C18 1.409(2) . ?
C14 C33 1.526(2) . ?
C15 C42 1.535(2) . ?
C15 C47 1.534(2) . ?
C16 C23 1.393(2) . ?
C16 C45 1.402(2) . ?
C17 C19 1.407(2) . ?
C17 C37 1.392(2) . ?
C19 C29 1.405(2) . ?
C19 B50 1.654(2) . ?
C20 C36 1.396(2) . ?
C20 B50 1.644(2) . ?
C20 C56 1.409(2) . ?
C21 C25 1.383(2) . ?
C22 C29 1.397(2) . ?
C22 C40 1.390(2) . ?
C23 C58 1.403(2) . ?
C24 C31 1.530(2) . ?
C26 C31 1.518(2) . ?
C27 B50 1.652(2) . ?
C27 C55 1.405(2) . ?
C27 C64 1.399(2) . ?
C28 C34 1.520(2) . ?
C30 C39 1.390(3) . ?
C30 C48 1.393(3) . ?
C32 C34 1.523(2) . ?
C32 C57 1.538(2) . ?
C33 C44 1.542(2) . ?
C33 C65 1.538(2) . ?
C34 C59 1.526(2) . ?
C35 B60 1.645(2) . ?
C36 C62 1.393(3) . ?
C37 C40 1.386(2) . ?
C38 C43 1.537(3) . ?
C38 C67 1.526(2) . ?
C39 C54 1.390(3) . ?
C41 C57 1.541(2) . ?
C41 B60 1.627(2) . ?
C45 C52 1.380(2) . ?
C49 C52 1.406(2) . ?
C49 C58 1.376(2) . ?
C51 C57 1.545(2) . ?
C51 C70 1.525(2) . ?
C53 C57 1.555(2) . ?
C53 C69 1.527(2) . ?
C55 C71 1.396(3) . ?
C56 C66 1.389(3) . ?
B60 O5 1.540(2) . ?
C61 C62 1.385(3) . ?
C61 C66 1.386(3) . ?
C63 C68 1.382(3) . ?
C63 C71 1.382(3) . ?
C64 C68 1.398(3) . ?
S1 O5 1.5329(12) . ?
S1 C3 1.8318(18) . ?
S1 O1 1.4256(14) . ?
S1 O2 1.4210(14) . ?
F1 C3 1.329(2) . ?
F2 C3 1.316(2) . ?
F3 C3 1.322(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
C16 N5 C31 122.52(13) . . ?
C35 N5 C16 109.59(13) . . ?
C35 N5 C31 126.95(13) . . ?
C18 N7 C34 117.97(12) . . ?
C41 N7 C18 128.01(13) . . ?
C41 N7 C34 114.01(13) . . ?
C12 C9 C48 115.11(15) . . ?
C12 C9 B50 123.79(14) . . ?
C48 C9 B50 120.94(15) . . ?
C23 N10 C38 124.36(13) . . ?
C35 N10 C23 109.75(13) . . ?
C35 N10 C38 125.39(13) . . ?
C18 C11 C15 123.90(14) . . ?
C21 C11 C15 118.13(14) . . ?
C21 C11 C18 117.95(15) . . ?
C9 C12 C54 122.92(16) . . ?
C25 C13 C14 122.16(15) . . ?
C13 C14 C18 117.22(15) . . ?
C13 C14 C33 116.65(14) . . ?
C18 C14 C33 126.10(15) . . ?
C11 C15 C42 111.15(13) . . ?
C11 C15 C47 111.25(13) . . ?
C47 C15 C42 109.03(13) . . ?
N5 C16 C45 131.89(15) . . ?
C23 C16 N5 106.59(13) . . ?
C23 C16 C45 121.52(14) . . ?
C37 C17 C19 122.99(16) . . ?
C11 C18 N7 116.56(13) . . ?
C11 C18 C14 121.69(15) . . ?
C14 C18 N7 121.55(14) . . ?
C17 C19 B50 124.07(15) . . ?
C29 C19 C17 114.53(15) . . ?
C29 C19 B50 121.40(14) . . ?
C36 C20 B50 123.50(15) . . ?
C36 C20 C56 115.15(16) . . ?
C56 C20 B50 121.29(15) . . ?
C25 C21 C11 121.67(15) . . ?
C40 C22 C29 119.82(16) . . ?
N10 C23 C58 131.98(15) . . ?
C16 C23 N10 106.48(13) . . ?
C16 C23 C58 121.53(15) . . ?
C21 C25 C13 119.26(16) . . ?
C55 C27 B50 120.91(15) . . ?
C64 C27 B50 123.94(16) . . ?
C64 C27 C55 115.13(16) . . ?
C22 C29 C19 123.40(15) . . ?
C39 C30 C48 120.32(16) . . ?
N5 C31 C24 109.00(13) . . ?
N5 C31 C26 112.03(13) . . ?
C26 C31 C24 113.27(14) . . ?
C34 C32 C57 107.17(13) . . ?
C14 C33 C44 110.60(14) . . ?
C14 C33 C65 111.58(14) . . ?
C65 C33 C44 108.19(14) . . ?
C28 C34 N7 113.59(13) . . ?
C28 C34 C32 111.97(13) . . ?
C28 C34 C59 109.01(13) . . ?
C32 C34 N7 100.35(12) . . ?
C32 C34 C59 113.28(14) . . ?
C59 C34 N7 108.46(12) . . ?
N5 C35 N10 107.56(13) . . ?
N5 C35 B60 124.00(14) . . ?
N10 C35 B60 128.41(14) . . ?
C62 C36 C20 122.48(17) . . ?
C40 C37 C17 120.54(16) . . ?
N10 C38 C43 112.87(14) . . ?
N10 C38 C67 108.88(14) . . ?
C67 C38 C43 111.23(14) . . ?
C30 C39 C54 118.39(16) . . ?
C37 C40 C22 118.72(15) . . ?
N7 C41 C57 109.86(14) . . ?
N7 C41 B60 128.15(14) . . ?
C57 C41 B60 121.33(14) . . ?
C52 C45 C16 116.71(15) . . ?
C30 C48 C9 122.85(17) . . ?
C58 C49 C52 121.98(15) . . ?
C9 B50 C19 107.89(13) . . ?
C9 B50 C27 110.41(13) . . ?
C20 B50 C9 109.00(13) . . ?
C20 B50 C19 111.65(13) . . ?
C20 B50 C27 109.34(14) . . ?
C27 B50 C19 108.55(13) . . ?
C70 C51 C57 117.70(14) . . ?
C45 C52 C49 121.64(16) . . ?
C69 C53 C57 116.12(14) . . ?
C39 C54 C12 120.42(17) . . ?
C71 C55 C27 122.77(18) . . ?
C66 C56 C20 122.95(18) . . ?
C32 C57 C41 102.90(12) . . ?
C32 C57 C51 111.37(13) . . ?
C32 C57 C53 113.05(14) . . ?
C41 C57 C51 113.96(14) . . ?
C41 C57 C53 106.83(13) . . ?
C51 C57 C53 108.66(13) . . ?
C49 C58 C23 116.59(15) . . ?
C41 B60 C35 118.37(13) . . ?
O5 B60 C35 108.60(13) . . ?
O5 B60 C41 113.00(13) . . ?
C62 C61 C66 118.56(17) . . ?
C61 C62 C36 120.73(18) . . ?
C68 C63 C71 118.98(18) . . ?
C68 C64 C27 122.67(18) . . ?
C56 C66 C61 120.12(18) . . ?
C63 C68 C64 120.30(19) . . ?
C63 C71 C55 120.14(19) . . ?
O5 S1 C3 99.38(7) . . ?
O1 S1 O5 112.71(7) . . ?
O1 S1 C3 105.41(8) . . ?
O2 S1 O5 111.06(8) . . ?
O2 S1 C3 106.51(8) . . ?
O2 S1 O1 119.38(8) . . ?
S1 O5 B60 120.02(10) . . ?
F1 C3 S1 107.90(12) . . ?
F2 C3 S1 110.71(12) . . ?
F2 C3 F1 108.49(14) . . ?
F2 C3 F3 109.42(15) . . ?
F3 C3 S1 111.52(12) . . ?
F3 C3 F1 108.72(14) . . ?
_shelx_res_file
;
TITL GB_MM1 in P2(1)/c
CELL 0.71073 14.2524 13.4771 28.1965 90 91.722 90
ZERR 4 0.0005 0.0005 0.0009 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H B F N O S
UNIT 240 296 8 12 12 12 4
L.S. 4
PLAN 20
TEMP 23
BOND
fmap 2
acta
REM /Users/david_ruiz06/Desktop/DAR/Structures%20aux%20rayons%20X/CAAC(Di
REM ppEt2)_BHOTf_BMIplusBPh4minus/files____/GB_MM1.hkl
WGHT 0.067000 2.180000
FVAR 0.11236
N5 5 0.161407 0.905479 0.344551 11.00000 0.01108 0.01235 =
0.01142 -0.00125 0.00120 -0.00027
N7 5 0.352888 0.592508 0.311755 11.00000 0.01034 0.01038 =
0.01134 0.00154 -0.00093 -0.00152
C9 1 -0.270092 0.720350 0.450226 11.00000 0.01030 0.01620 =
0.01573 -0.00114 0.00203 -0.00217
N10 5 0.082815 0.765953 0.344619 11.00000 0.01155 0.01306 =
0.01265 0.00030 -0.00075 0.00032
C11 1 0.433219 0.602455 0.236399 11.00000 0.01298 0.01092 =
0.01376 0.00081 -0.00057 0.00217
C12 1 -0.301118 0.764740 0.407882 11.00000 0.01149 0.01505 =
0.01816 -0.00041 0.00137 -0.00143
AFIX 43
H12 2 -0.324788 0.828983 0.408933 11.00000 -1.20000
AFIX 0
C13 1 0.303073 0.474665 0.192839 11.00000 0.01627 0.01451 =
0.01589 -0.00338 -0.00271 -0.00021
AFIX 43
H13 2 0.259292 0.433461 0.177657 11.00000 -1.20000
AFIX 0
C14 1 0.289229 0.502174 0.239881 11.00000 0.01337 0.01077 =
0.01463 0.00042 -0.00051 0.00237
C15 1 0.504529 0.676934 0.256887 11.00000 0.01375 0.01649 =
0.01110 -0.00005 0.00227 -0.00209
AFIX 13
H15 2 0.498307 0.679184 0.291390 11.00000 -1.20000
AFIX 0
C16 1 0.076893 0.925042 0.366736 11.00000 0.01193 0.01701 =
0.00914 0.00115 -0.00006 0.00056
C17 1 -0.428670 0.649224 0.509548 11.00000 0.01740 0.01606 =
0.01603 -0.00098 0.00145 0.00144
AFIX 43
H17 2 -0.403660 0.611221 0.485468 11.00000 -1.20000
AFIX 0
C18 1 0.355927 0.566519 0.261292 11.00000 0.01302 0.01028 =
0.01071 0.00023 0.00014 0.00337
C19 1 -0.379073 0.733878 0.525316 11.00000 0.01452 0.01458 =
0.01186 0.00254 -0.00439 0.00172
C20 1 -0.188379 0.740209 0.536550 11.00000 0.01681 0.01290 =
0.01719 0.00104 -0.00177 -0.00218
C21 1 0.443870 0.569976 0.190039 11.00000 0.01502 0.01751 =
0.01409 0.00189 0.00210 0.00026
AFIX 43
H21 2 0.495440 0.591376 0.173376 11.00000 -1.20000
AFIX 0
C22 1 -0.506498 0.757615 0.581568 11.00000 0.01802 0.01930 =
0.01274 0.00039 0.00154 0.00411
AFIX 43
H22 2 -0.531608 0.794542 0.605994 11.00000 -1.20000
AFIX 0
C23 1 0.026421 0.836550 0.366243 11.00000 0.01371 0.01509 =
0.01035 -0.00020 -0.00077 0.00246
C24 1 0.173137 1.058519 0.297314 11.00000 0.01825 0.01732 =
0.01757 0.00308 0.00128 -0.00060
AFIX 137
H24A 2 0.141138 1.022305 0.272370 11.00000 -1.50000
H24B 2 0.216488 1.104299 0.283808 11.00000 -1.50000
H24C 2 0.128173 1.094431 0.315298 11.00000 -1.50000
AFIX 0
C25 1 0.379726 0.506683 0.168108 11.00000 0.02053 0.01873 =
0.01138 -0.00235 -0.00050 0.00207
AFIX 43
H25 2 0.388047 0.485879 0.137068 11.00000 -1.20000
AFIX 0
C26 1 0.274766 1.036077 0.372354 11.00000 0.01861 0.01676 =
0.01767 -0.00281 -0.00028 -0.00248
AFIX 137
H26A 2 0.229333 1.073053 0.389551 11.00000 -1.50000
H26B 2 0.322507 1.080222 0.361583 11.00000 -1.50000
H26C 2 0.302841 0.986600 0.392748 11.00000 -1.50000
AFIX 0
C27 1 -0.283088 0.894200 0.497883 11.00000 0.02228 0.01587 =
0.00914 -0.00063 0.00574 -0.00085
C28 1 0.506368 0.498890 0.331533 11.00000 0.01451 0.01432 =
0.01611 0.00122 -0.00021 0.00212
AFIX 137
H28A 2 0.501427 0.470097 0.300417 11.00000 -1.50000
H28B 2 0.534175 0.451746 0.353264 11.00000 -1.50000
H28C 2 0.544913 0.557236 0.330636 11.00000 -1.50000
AFIX 0
C29 1 -0.421728 0.786203 0.562005 11.00000 0.01888 0.01623 =
0.01367 -0.00125 -0.00306 -0.00230
AFIX 43
H29 2 -0.391993 0.842795 0.573880 11.00000 -1.20000
AFIX 0
C30 1 -0.232774 0.573749 0.402307 11.00000 0.01959 0.01750 =
0.02759 -0.00493 0.00423 0.00022
AFIX 43
H30 2 -0.210040 0.509147 0.401074 11.00000 -1.20000
AFIX 0
C31 1 0.226710 0.986031 0.329936 11.00000 0.01313 0.01285 =
0.01487 -0.00022 0.00318 -0.00198
AFIX 13
H31 2 0.275745 0.955157 0.311279 11.00000 -1.20000
AFIX 0
C32 1 0.413471 0.595621 0.390670 11.00000 0.01378 0.02012 =
0.01266 -0.00028 -0.00286 0.00371
AFIX 23
H32A 2 0.472674 0.631161 0.392018 11.00000 -1.20000
H32B 2 0.408051 0.557753 0.419714 11.00000 -1.20000
AFIX 0
C33 1 0.201282 0.462036 0.262763 11.00000 0.01435 0.01619 =
0.01504 -0.00381 0.00018 -0.00233
AFIX 13
H33 2 0.200596 0.484780 0.295763 11.00000 -1.20000
AFIX 0
C34 1 0.409106 0.526750 0.347819 11.00000 0.01315 0.01325 =
0.01200 0.00352 -0.00223 0.00063
C35 1 0.164570 0.808460 0.331885 11.00000 0.01127 0.01329 =
0.01057 0.00054 -0.00235 0.00044
C36 1 -0.193964 0.717996 0.584750 11.00000 0.01790 0.01813 =
0.01865 0.00233 -0.00123 -0.00319
AFIX 43
H36 2 -0.252317 0.719948 0.598621 11.00000 -1.20000
AFIX 0
C37 1 -0.513463 0.619776 0.528352 11.00000 0.01761 0.01554 =
0.02162 -0.00173 -0.00171 -0.00228
AFIX 43
H37 2 -0.543704 0.563357 0.516614 11.00000 -1.20000
AFIX 0
C38 1 0.051617 0.663986 0.331761 11.00000 0.01353 0.01170 =
0.02587 -0.00347 -0.00051 -0.00024
AFIX 13
H38 2 0.105351 0.628721 0.318909 11.00000 -1.20000
AFIX 0
C39 1 -0.263768 0.620771 0.360847 11.00000 0.01758 0.02599 =
0.02013 -0.00887 0.00525 -0.00604
AFIX 43
H39 2 -0.261520 0.588645 0.331713 11.00000 -1.20000
AFIX 0
C40 1 -0.553189 0.673851 0.564426 11.00000 0.01273 0.02007 =
0.01781 0.00494 0.00046 -0.00017
AFIX 43
H40 2 -0.609990 0.654459 0.576919 11.00000 -1.20000
AFIX 0
C41 1 0.309269 0.666858 0.331089 11.00000 0.00897 0.01339 =
0.01250 -0.00021 0.00096 -0.00309
C42 1 0.486405 0.781363 0.236929 11.00000 0.01873 0.01553 =
0.01856 0.00173 0.00193 -0.00251
AFIX 137
H42A 2 0.492190 0.780394 0.203099 11.00000 -1.50000
H42B 2 0.531446 0.826762 0.250670 11.00000 -1.50000
H42C 2 0.424243 0.802254 0.244534 11.00000 -1.50000
AFIX 0
C43 1 0.017486 0.604739 0.374503 11.00000 0.01632 0.01763 =
0.04141 0.00835 0.00104 -0.00223
AFIX 137
H43A 2 0.053511 0.623322 0.402418 11.00000 -1.50000
H43B 2 0.025270 0.535080 0.368692 11.00000 -1.50000
H43C 2 -0.047644 0.618808 0.379097 11.00000 -1.50000
AFIX 0
C44 1 0.112202 0.500393 0.236342 11.00000 0.01331 0.02499 =
0.02029 -0.00575 -0.00063 -0.00105
AFIX 137
H44A 2 0.113222 0.571597 0.235568 11.00000 -1.50000
H44B 2 0.057671 0.478338 0.252514 11.00000 -1.50000
H44C 2 0.110249 0.475125 0.204495 11.00000 -1.50000
AFIX 0
C45 1 0.041183 1.011564 0.387048 11.00000 0.01766 0.01453 =
0.01534 -0.00102 0.00105 -0.00045
AFIX 43
H45 2 0.075343 1.070361 0.388016 11.00000 -1.20000
AFIX 0
C47 1 0.605304 0.645920 0.246210 11.00000 0.01393 0.02325 =
0.01450 -0.00195 0.00109 -0.00134
AFIX 137
H47A 2 0.614905 0.578009 0.255413 11.00000 -1.50000
H47B 2 0.648741 0.687501 0.263679 11.00000 -1.50000
H47C 2 0.615318 0.652846 0.212856 11.00000 -1.50000
AFIX 0
C48 1 -0.235603 0.622931 0.445694 11.00000 0.01881 0.01805 =
0.02036 0.00306 0.00219 0.00179
AFIX 43
H48 2 -0.213784 0.590044 0.472845 11.00000 -1.20000
AFIX 0
C49 1 -0.098953 0.916386 0.403901 11.00000 0.01304 0.02611 =
0.01510 0.00037 0.00229 0.00070
AFIX 43
H49 2 -0.158805 0.915528 0.416155 11.00000 -1.20000
AFIX 0
B50 3 -0.279511 0.772116 0.502828 11.00000 0.01571 0.01382 =
0.01223 0.00104 0.00054 -0.00114
C51 1 0.357951 0.772595 0.404370 11.00000 0.01698 0.02194 =
0.01462 -0.00599 -0.00383 0.00328
AFIX 23
H51A 2 0.304802 0.816354 0.398569 11.00000 -1.20000
H51B 2 0.367151 0.767081 0.438493 11.00000 -1.20000
AFIX 0
C52 1 -0.047142 1.005204 0.405535 11.00000 0.01814 0.02043 =
0.01443 -0.00254 0.00285 0.00400
AFIX 43
H52 2 -0.073072 1.061039 0.419424 11.00000 -1.20000
AFIX 0
C53 1 0.241116 0.633194 0.409609 11.00000 0.01601 0.02339 =
0.01435 0.00350 0.00080 0.00335
AFIX 23
H53A 2 0.196486 0.687543 0.409370 11.00000 -1.20000
H53B 2 0.213361 0.579907 0.390798 11.00000 -1.20000
AFIX 0
C54 1 -0.298202 0.716968 0.363988 11.00000 0.01638 0.02566 =
0.01524 0.00015 -0.00076 -0.00502
AFIX 43
H54 2 -0.319435 0.749731 0.336692 11.00000 -1.20000
AFIX 0
C55 1 -0.365727 0.942777 0.482474 11.00000 0.02607 0.01896 =
0.01817 0.00104 0.00347 0.00381
AFIX 43
H55 2 -0.419388 0.905032 0.476430 11.00000 -1.20000
AFIX 0
C56 1 -0.097222 0.737789 0.518597 11.00000 0.01952 0.03539 =
0.02049 0.00643 0.00119 0.00002
AFIX 43
H56 2 -0.089593 0.752886 0.486761 11.00000 -1.20000
AFIX 0
C57 1 0.331188 0.668905 0.384945 11.00000 0.01294 0.01850 =
0.00954 -0.00071 -0.00131 0.00217
C58 1 -0.063743 0.830705 0.384715 11.00000 0.01343 0.01904 =
0.01427 0.00151 0.00091 -0.00202
AFIX 43
H58 2 -0.097958 0.771937 0.384028 11.00000 -1.20000
AFIX 0
C59 1 0.353179 0.432149 0.356207 11.00000 0.01532 0.01792 =
0.02297 0.00829 -0.00309 -0.00348
AFIX 137
H59A 2 0.290720 0.449201 0.365104 11.00000 -1.50000
H59B 2 0.383301 0.394309 0.381168 11.00000 -1.50000
H59C 2 0.350327 0.393419 0.327626 11.00000 -1.50000
AFIX 0
B60 3 0.252859 0.757232 0.304687 11.00000 0.01396 0.01527 =
0.01195 0.00057 -0.00119 0.00075
AFIX 13
H60 2 0.299224 0.810347 0.301554 11.00000 -1.20000
AFIX 0
C61 1 -0.026971 0.690738 0.593861 11.00000 0.01985 0.03671 =
0.03337 0.00813 -0.01189 -0.00130
AFIX 43
H61 2 0.025452 0.674040 0.612620 11.00000 -1.20000
AFIX 0
C62 1 -0.115433 0.693022 0.612841 11.00000 0.02781 0.03328 =
0.01787 0.00858 -0.00536 -0.00251
AFIX 43
H62 2 -0.122488 0.677713 0.644697 11.00000 -1.20000
AFIX 0
C63 1 -0.292457 1.103741 0.484821 11.00000 0.06117 0.01376 =
0.02768 -0.00042 0.02137 0.00309
AFIX 43
H63 2 -0.295179 1.172010 0.480174 11.00000 -1.20000
AFIX 0
C64 1 -0.206128 0.956359 0.507282 11.00000 0.02776 0.02281 =
0.01223 -0.00366 0.00534 -0.00509
AFIX 43
H64 2 -0.150036 0.928165 0.518288 11.00000 -1.20000
AFIX 0
C65 1 0.198897 0.347959 0.262161 11.00000 0.02345 0.01640 =
0.02161 -0.00312 0.00107 -0.00595
AFIX 137
H65A 2 0.202798 0.324815 0.230081 11.00000 -1.50000
H65B 2 0.141327 0.325250 0.275262 11.00000 -1.50000
H65C 2 0.251079 0.322603 0.280764 11.00000 -1.50000
AFIX 0
C66 1 -0.018247 0.713871 0.546308 11.00000 0.01449 0.04688 =
0.03520 0.00553 -0.00022 -0.00032
AFIX 43
H66 2 0.040604 0.713377 0.532930 11.00000 -1.20000
AFIX 0
C67 1 -0.024465 0.670565 0.292658 11.00000 0.01567 0.02467 =
0.03033 -0.01026 -0.00446 -0.00003
AFIX 137
H67A 2 -0.076948 0.707329 0.303996 11.00000 -1.50000
H67B 2 -0.044494 0.604935 0.283824 11.00000 -1.50000
H67C 2 0.000174 0.703570 0.265548 11.00000 -1.50000
AFIX 0
C68 1 -0.210133 1.059147 0.500800 11.00000 0.04774 0.02280 =
0.02138 -0.00783 0.01583 -0.01462
AFIX 43
H68 2 -0.157146 1.097672 0.507272 11.00000 -1.20000
AFIX 0
C69 1 0.254448 0.596623 0.460622 11.00000 0.02545 0.04381 =
0.01823 0.01130 0.00296 0.00417
AFIX 137
H69A 2 0.286413 0.533920 0.460752 11.00000 -1.50000
H69B 2 0.194259 0.588944 0.474572 11.00000 -1.50000
H69C 2 0.291054 0.644015 0.478615 11.00000 -1.50000
AFIX 0
C70 1 0.444608 0.822582 0.384737 11.00000 0.01722 0.02501 =
0.03227 -0.00692 -0.00443 -0.00160
AFIX 137
H70A 2 0.437264 0.828720 0.350909 11.00000 -1.50000
H70B 2 0.499126 0.783198 0.392356 11.00000 -1.50000
H70C 2 0.451972 0.887288 0.398591 11.00000 -1.50000
AFIX 0
C71 1 -0.370684 1.045343 0.475852 11.00000 0.04327 0.02102 =
0.02809 0.00634 0.01201 0.01238
AFIX 43
H71 2 -0.426749 1.074411 0.465384 11.00000 -1.20000
AFIX 0
S1 7 0.194085 0.814784 0.218510 11.00000 0.02230 0.01884 =
0.01242 0.00178 -0.00037 0.00687
O5 6 0.220514 0.731642 0.253522 11.00000 0.02029 0.01643 =
0.01221 -0.00061 -0.00209 0.00369
F1 4 0.201662 0.815068 0.127474 11.00000 0.02827 0.03031 =
0.01494 0.00640 -0.00205 0.00438
F2 4 0.312260 0.731560 0.162016 11.00000 0.02431 0.04180 =
0.01963 0.00134 0.00279 0.01390
F3 4 0.172575 0.670843 0.156524 11.00000 0.04955 0.02708 =
0.02156 -0.00280 -0.00136 -0.01097
C3 1 0.222199 0.752915 0.162865 11.00000 0.02097 0.02062 =
0.01515 0.00307 -0.00071 0.00270
O1 6 0.256182 0.897551 0.222107 11.00000 0.03970 0.01824 =
0.01971 0.00150 -0.00551 0.00129
O2 6 0.095565 0.831291 0.216834 11.00000 0.02540 0.03943 =
0.02521 0.00787 0.00351 0.01475
HKLF 4
REM GB_MM1 in P2(1)/c
REM R1 = 0.0479 for 8741 Fo > 4sig(Fo) and 0.0620 for all 10835 data
REM 661 parameters refined using 0 restraints
END
WGHT 0.0616 2.2914
REM Highest difference peak 0.556, deepest hole -0.492, 1-sigma level 0.076
Q1 1 0.1346 0.7616 0.2207 11.00000 0.05 0.56
Q2 1 0.3738 0.6366 0.3890 11.00000 0.05 0.40
Q3 1 0.0700 0.9566 0.3830 11.00000 0.05 0.38
Q4 1 0.4143 0.5542 0.3701 11.00000 0.05 0.37
Q5 1 0.0666 0.7201 0.3404 11.00000 0.05 0.37
Q6 1 0.0465 0.7958 0.3534 11.00000 0.05 0.36
Q7 1 0.4672 0.6379 0.2465 11.00000 0.05 0.34
Q8 1 0.5510 0.6619 0.2510 11.00000 0.05 0.34
Q9 1 -0.0015 0.9952 0.4064 11.00000 0.05 0.33
Q10 1 -0.3301 0.7507 0.5139 11.00000 0.05 0.32
Q11 1 0.0523 0.8848 0.3688 11.00000 0.05 0.32
Q12 1 -0.0188 0.8319 0.3694 11.00000 0.05 0.32
Q13 1 0.4484 0.6280 0.2418 11.00000 0.05 0.31
Q14 1 0.0367 0.6391 0.3560 11.00000 0.05 0.30
Q15 1 -0.0758 0.6696 0.6004 11.00000 0.05 0.30
Q16 1 -0.0714 0.6927 0.6005 11.00000 0.05 0.29
Q17 1 0.0148 0.6696 0.3117 11.00000 0.05 0.28
Q18 1 -0.5207 0.6376 0.5517 11.00000 0.05 0.28
Q19 1 -0.0555 0.9461 0.4190 11.00000 0.05 0.27
Q20 1 0.3846 0.4825 0.3518 11.00000 0.05 0.27
;
_shelx_res_checksum 57184
_database_code_depnum_ccdc_archive 'CCDC 1001686'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_shelxl
_audit_creation_date 2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_chemical_name_common ?
_chemical_name_systematic
;
?
;
_chemical_formula_moiety 'C23 H37 B F3 N O3 S'
_chemical_formula_sum 'C23 H37 B F3 N O3 S'
_chemical_formula_weight 475.41
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 11.1389(6)
_cell_length_b 13.5546(7)
_cell_length_c 16.2662(9)
_cell_angle_alpha 90.00
_cell_angle_beta 95.4560(10)
_cell_angle_gamma 90.00
_cell_volume 2444.8(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9964
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 29.17
_cell_measurement_theta_min 2.37
_exptl_absorpt_coefficient_mu 0.180
_exptl_absorpt_correction_T_max 0.9736
_exptl_absorpt_correction_T_min 0.9448
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour ?
_exptl_crystal_density_diffrn 1.292
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description ?
_exptl_crystal_F_000 1016
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.15
_exptl_special_details
;
?
;
_diffrn_reflns_av_R_equivalents 0.0132
_diffrn_reflns_av_unetI/netI 0.0121
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 19841
_diffrn_reflns_theta_full 29.36
_diffrn_reflns_theta_max 29.36
_diffrn_reflns_theta_min 2.13
_diffrn_ambient_temperature 0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_decay_% ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number 0
_reflns_number_gt 5747
_reflns_number_total 6162
_reflns_threshold_expression >2sigma(I)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.436
_refine_diff_density_min -0.320
_refine_diff_density_rms 0.042
_refine_ls_extinction_coef ?
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 401
_refine_ls_number_reflns 6162
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0346
_refine_ls_R_factor_gt 0.0326
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.9430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0872
_refine_ls_wR_factor_ref 0.0889
_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 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53452(7) 0.21453(6) 0.69712(5) 0.01247(15) Uani 1 1 d . . .
B1 B 0.75613(9) 0.25294(8) 0.73213(6) 0.0166(2) Uani 1 1 d . . .
C1 C 0.64513(8) 0.19990(7) 0.68006(5) 0.01287(16) Uani 1 1 d . . .
C2 C 0.64974(8) 0.12323(7) 0.61251(5) 0.01393(17) Uani 1 1 d . . .
C3 C 0.51531(8) 0.10284(8) 0.58503(6) 0.01725(18) Uani 1 1 d . . .
C4 C 0.43887(8) 0.15311(7) 0.64674(6) 0.01456(17) Uani 1 1 d . . .
C5 C 0.50467(8) 0.28360(7) 0.76151(5) 0.01318(17) Uani 1 1 d . . .
C6 C 0.47944(8) 0.38253(7) 0.73891(6) 0.01480(17) Uani 1 1 d . . .
C7 C 0.44997(9) 0.44733(7) 0.80080(6) 0.01825(18) Uani 1 1 d . . .
C8 C 0.44622(9) 0.41553(8) 0.88161(6) 0.01969(19) Uani 1 1 d . . .
C9 C 0.47511(9) 0.31892(8) 0.90279(6) 0.01790(18) Uani 1 1 d . . .
C10 C 0.50630(8) 0.25052(7) 0.84385(5) 0.01436(17) Uani 1 1 d . . .
C11 C 0.71562(9) 0.16213(8) 0.53937(6) 0.01829(18) Uani 1 1 d . . .
C12 C 0.68092(11) 0.26678(9) 0.51165(7) 0.0244(2) Uani 1 1 d . . .
C13 C 0.71541(8) 0.03156(7) 0.65228(6) 0.01643(18) Uani 1 1 d . . .
C14 C 0.73118(10) -0.05259(8) 0.59182(6) 0.0215(2) Uani 1 1 d . . .
C15 C 0.38193(10) 0.07967(8) 0.70227(7) 0.0228(2) Uani 1 1 d . . .
C16 C 0.34017(9) 0.21802(8) 0.60425(7) 0.0213(2) Uani 1 1 d . . .
C17 C 0.48514(9) 0.42385(7) 0.65212(6) 0.01716(18) Uani 1 1 d . . .
C18 C 0.36441(10) 0.47024(8) 0.61864(7) 0.0237(2) Uani 1 1 d . . .
C19 C 0.58623(10) 0.50056(8) 0.64944(7) 0.0226(2) Uani 1 1 d . . .
C20 C 0.54203(8) 0.14713(7) 0.87367(6) 0.01616(17) Uani 1 1 d . . .
C21 C 0.43831(10) 0.09572(8) 0.91282(6) 0.0217(2) Uani 1 1 d . . .
C22 C 0.65292(9) 0.14849(9) 0.93761(6) 0.0222(2) Uani 1 1 d . . .
C23 C 1.07021(9) 0.29166(8) 0.77191(7) 0.0207(2) Uani 1 1 d . . .
F1 F 1.10471(7) 0.20028(5) 0.79128(5) 0.03468(17) Uani 1 1 d . . .
F2 F 1.16878(6) 0.34508(5) 0.76524(5) 0.03402(17) Uani 1 1 d . . .
F3 F 1.01320(6) 0.32825(6) 0.83310(4) 0.03436(17) Uani 1 1 d . . .
S1 S 0.97343(2) 0.29453(2) 0.674891(15) 0.02312(8) Uani 1 1 d . . .
O1 O 0.87391(6) 0.22559(6) 0.69263(4) 0.01953(15) Uani 1 1 d . . .
O2 O 1.04386(8) 0.24962(10) 0.61673(6) 0.0462(3) Uani 1 1 d . . .
O3 O 0.93673(8) 0.39482(7) 0.66486(7) 0.0421(3) Uani 1 1 d . . .
H3A H 0.4952(13) 0.1315(11) 0.5294(9) 0.0279(6) Uiso 1 1 d . . .
H3B H 0.4993(13) 0.0327(11) 0.5839(9) 0.0279(6) Uiso 1 1 d . . .
H7 H 0.4313(13) 0.5149(11) 0.7865(9) 0.0279(6) Uiso 1 1 d . . .
H8 H 0.4253(13) 0.4614(11) 0.9229(9) 0.0279(6) Uiso 1 1 d . . .
H9 H 0.4741(13) 0.2975(11) 0.9592(9) 0.0279(6) Uiso 1 1 d . . .
H11A H 0.8038(13) 0.1597(11) 0.5536(9) 0.0279(6) Uiso 1 1 d . . .
H11B H 0.6957(13) 0.1156(11) 0.4927(9) 0.0279(6) Uiso 1 1 d . . .
H12A H 0.5965(14) 0.2738(11) 0.4990(9) 0.0279(6) Uiso 1 1 d . . .
H12B H 0.7188(13) 0.2841(11) 0.4631(9) 0.0279(6) Uiso 1 1 d . . .
H12C H 0.7046(13) 0.3142(11) 0.5534(9) 0.0279(6) Uiso 1 1 d . . .
H13A H 0.7952(14) 0.0518(11) 0.6772(9) 0.0279(6) Uiso 1 1 d . . .
H13B H 0.6703(13) 0.0078(11) 0.6978(9) 0.0279(6) Uiso 1 1 d . . .
H14A H 0.6529(13) -0.0754(11) 0.5658(9) 0.0279(6) Uiso 1 1 d . . .
H14B H 0.7703(13) -0.1080(11) 0.6207(9) 0.0279(6) Uiso 1 1 d . . .
H14C H 0.7807(13) -0.0338(11) 0.5482(9) 0.0279(6) Uiso 1 1 d . . .
H15A H 0.3374(13) 0.1118(11) 0.7427(9) 0.0279(6) Uiso 1 1 d . . .
H15B H 0.4432(14) 0.0358(11) 0.7313(9) 0.0279(6) Uiso 1 1 d . . .
H15C H 0.3233(13) 0.0397(11) 0.6684(9) 0.0279(6) Uiso 1 1 d . . .
H16A H 0.2814(13) 0.1757(11) 0.5748(9) 0.0279(6) Uiso 1 1 d . . .
H16B H 0.3707(13) 0.2624(11) 0.5640(9) 0.0279(6) Uiso 1 1 d . . .
H16C H 0.2993(13) 0.2542(11) 0.6446(9) 0.0279(6) Uiso 1 1 d . . .
H17 H 0.5031(13) 0.3695(11) 0.6158(9) 0.0279(6) Uiso 1 1 d . . .
H18A H 0.2965(14) 0.4243(11) 0.6211(9) 0.0279(6) Uiso 1 1 d . . .
H18B H 0.3695(13) 0.4909(11) 0.5615(9) 0.0279(6) Uiso 1 1 d . . .
H18C H 0.3474(13) 0.5276(11) 0.6493(9) 0.0279(6) Uiso 1 1 d . . .
H19A H 0.5734(13) 0.5569(11) 0.6845(9) 0.0279(6) Uiso 1 1 d . . .
H19B H 0.5876(13) 0.5248(11) 0.5938(9) 0.0279(6) Uiso 1 1 d . . .
H19C H 0.6641(14) 0.4723(11) 0.6666(9) 0.0279(6) Uiso 1 1 d . . .
H20 H 0.5632(13) 0.1087(11) 0.8263(9) 0.0279(6) Uiso 1 1 d . . .
H21A H 0.4266(13) 0.1246(11) 0.9676(9) 0.0279(6) Uiso 1 1 d . . .
H21B H 0.4564(13) 0.0258(11) 0.9220(9) 0.0279(6) Uiso 1 1 d . . .
H21C H 0.3622(13) 0.1010(11) 0.8779(9) 0.0279(6) Uiso 1 1 d . . .
H22A H 0.7204(13) 0.1808(11) 0.9167(9) 0.0279(6) Uiso 1 1 d . . .
H22B H 0.6758(13) 0.0802(11) 0.9515(9) 0.0279(6) Uiso 1 1 d . . .
H22C H 0.6345(13) 0.1809(11) 0.9877(9) 0.0279(6) Uiso 1 1 d . . .
H1 H 0.7653(13) 0.2210(11) 0.7949(9) 0.0279(6) Uiso 1 1 d . . .
H2 H 0.7443(13) 0.3330(11) 0.7320(9) 0.0279(6) 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
N1 0.0117(3) 0.0136(3) 0.0119(3) -0.0019(3) 0.0000(3) -0.0003(3)
B1 0.0107(4) 0.0226(5) 0.0167(4) -0.0044(4) 0.0022(4) -0.0020(4)
C1 0.0131(4) 0.0142(4) 0.0112(4) 0.0009(3) 0.0010(3) 0.0006(3)
C2 0.0118(4) 0.0174(4) 0.0124(4) -0.0025(3) 0.0004(3) 0.0011(3)
C3 0.0132(4) 0.0216(5) 0.0165(4) -0.0065(3) -0.0009(3) 0.0008(3)
C4 0.0109(4) 0.0167(4) 0.0157(4) -0.0043(3) -0.0010(3) -0.0011(3)
C5 0.0104(4) 0.0153(4) 0.0139(4) -0.0037(3) 0.0016(3) -0.0003(3)
C6 0.0120(4) 0.0162(4) 0.0161(4) -0.0014(3) 0.0005(3) -0.0002(3)
C7 0.0173(4) 0.0159(4) 0.0217(4) -0.0027(3) 0.0023(3) 0.0014(3)
C8 0.0201(4) 0.0196(5) 0.0201(4) -0.0064(4) 0.0056(4) 0.0006(4)
C9 0.0178(4) 0.0210(5) 0.0155(4) -0.0028(3) 0.0046(3) -0.0010(3)
C10 0.0117(4) 0.0164(4) 0.0150(4) -0.0017(3) 0.0020(3) -0.0011(3)
C11 0.0175(4) 0.0251(5) 0.0125(4) -0.0012(3) 0.0028(3) 0.0014(4)
C12 0.0293(5) 0.0265(5) 0.0177(4) 0.0039(4) 0.0037(4) 0.0005(4)
C13 0.0156(4) 0.0178(4) 0.0155(4) -0.0022(3) -0.0001(3) 0.0025(3)
C14 0.0214(5) 0.0210(5) 0.0216(5) -0.0060(4) -0.0005(4) 0.0053(4)
C15 0.0210(5) 0.0256(5) 0.0217(5) -0.0029(4) 0.0024(4) -0.0097(4)
C16 0.0140(4) 0.0220(5) 0.0263(5) -0.0068(4) -0.0058(4) 0.0038(4)
C17 0.0185(4) 0.0166(4) 0.0160(4) 0.0003(3) -0.0004(3) 0.0009(3)
C18 0.0235(5) 0.0206(5) 0.0255(5) 0.0004(4) -0.0058(4) 0.0038(4)
C19 0.0242(5) 0.0219(5) 0.0214(5) 0.0030(4) 0.0012(4) -0.0033(4)
C20 0.0175(4) 0.0169(4) 0.0144(4) -0.0001(3) 0.0031(3) 0.0012(3)
C21 0.0242(5) 0.0205(5) 0.0216(5) 0.0010(4) 0.0078(4) -0.0023(4)
C22 0.0202(5) 0.0299(5) 0.0163(4) 0.0019(4) 0.0009(4) 0.0034(4)
C23 0.0167(4) 0.0197(5) 0.0247(5) -0.0011(4) -0.0027(4) -0.0011(3)
F1 0.0367(4) 0.0222(3) 0.0419(4) 0.0041(3) -0.0132(3) 0.0039(3)
F2 0.0165(3) 0.0319(4) 0.0524(4) -0.0049(3) -0.0031(3) -0.0079(3)
F3 0.0291(3) 0.0465(4) 0.0268(3) -0.0124(3) -0.0003(3) 0.0003(3)
S1 0.01336(12) 0.03793(16) 0.01808(12) 0.00740(10) 0.00152(9) -0.00509(9)
O1 0.0116(3) 0.0249(4) 0.0224(3) -0.0050(3) 0.0036(3) -0.0025(3)
O2 0.0211(4) 0.0953(9) 0.0237(4) -0.0077(5) 0.0104(3) -0.0076(5)
O3 0.0262(4) 0.0406(5) 0.0577(6) 0.0315(5) -0.0054(4) -0.0070(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
N1 C1 1.3037(11) . ?
N1 C4 1.5277(11) . ?
N1 C5 1.4663(11) . ?
B1 C1 1.6012(13) . ?
B1 O1 1.5593(12) . ?
B1 H1 1.104(15) . ?
B1 H2 1.093(15) . ?
C1 C2 1.5168(12) . ?
C2 C3 1.5464(12) . ?
C2 C11 1.5487(13) . ?
C2 C13 1.5516(13) . ?
C3 C4 1.5360(12) . ?
C3 H3A 0.991(15) . ?
C3 H3B 0.968(15) . ?
C4 C15 1.5226(14) . ?
C4 C16 1.5218(13) . ?
C5 C6 1.4116(13) . ?
C5 C10 1.4110(12) . ?
C6 C7 1.3984(13) . ?
C6 C17 1.5257(13) . ?
C7 C8 1.3877(14) . ?
C7 H7 0.963(15) . ?
C8 C9 1.3842(14) . ?
C8 H8 0.960(15) . ?
C9 C10 1.4009(13) . ?
C9 H9 0.963(15) . ?
C10 C20 1.5235(13) . ?
C11 C12 1.5269(15) . ?
C11 H11A 0.988(15) . ?
C11 H11B 0.996(15) . ?
C12 H12A 0.948(15) . ?
C12 H12B 0.959(15) . ?
C12 H12C 0.954(15) . ?
C13 C14 1.5270(13) . ?
C13 H13A 0.980(15) . ?
C13 H13B 0.988(15) . ?
C14 H14A 0.982(15) . ?
C14 H14B 0.966(15) . ?
C14 H14C 0.973(15) . ?
C15 H15A 0.964(15) . ?
C15 H15B 0.990(15) . ?
C15 H15C 0.978(15) . ?
C16 H16A 0.963(15) . ?
C16 H16B 0.974(15) . ?
C16 H16C 0.968(15) . ?
C17 C18 1.5365(14) . ?
C17 C19 1.5363(14) . ?
C17 H17 0.976(15) . ?
C18 H18A 0.984(15) . ?
C18 H18B 0.978(15) . ?
C18 H18C 0.952(15) . ?
C19 H19A 0.972(15) . ?
C19 H19B 0.964(15) . ?
C19 H19C 0.965(15) . ?
C20 C21 1.5380(13) . ?
C20 C22 1.5373(14) . ?
C20 H20 0.978(15) . ?
C21 H21A 0.993(15) . ?
C21 H21B 0.977(15) . ?
C21 H21C 0.977(15) . ?
C22 H22A 0.960(15) . ?
C22 H22B 0.980(15) . ?
C22 H22C 0.965(15) . ?
C23 F1 1.3260(12) . ?
C23 F2 1.3282(12) . ?
C23 F3 1.3267(13) . ?
C23 S1 1.8250(11) . ?
S1 O1 1.4987(7) . ?
S1 O2 1.4220(10) . ?
S1 O3 1.4245(10) . ?
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 N1 C4 115.33(7) . . ?
C1 N1 C5 122.16(8) . . ?
C5 N1 C4 122.49(7) . . ?
C1 B1 H1 108.2(8) . . ?
C1 B1 H2 110.9(8) . . ?
O1 B1 C1 108.24(7) . . ?
O1 B1 H1 106.2(7) . . ?
O1 B1 H2 110.0(8) . . ?
H1 B1 H2 113.1(11) . . ?
N1 C1 B1 121.13(8) . . ?
N1 C1 C2 110.87(8) . . ?
C2 C1 B1 127.82(8) . . ?
C1 C2 C3 103.49(7) . . ?
C1 C2 C11 111.99(8) . . ?
C1 C2 C13 107.09(7) . . ?
C3 C2 C11 110.81(7) . . ?
C3 C2 C13 112.49(8) . . ?
C11 C2 C13 110.73(7) . . ?
C2 C3 H3A 108.8(8) . . ?
C2 C3 H3B 110.7(9) . . ?
C4 C3 C2 108.27(7) . . ?
C4 C3 H3A 109.4(8) . . ?
C4 C3 H3B 109.6(9) . . ?
H3A C3 H3B 110.0(12) . . ?
N1 C4 C3 101.00(7) . . ?
C15 C4 N1 110.28(7) . . ?
C15 C4 C3 112.69(8) . . ?
C16 C4 N1 111.44(8) . . ?
C16 C4 C3 112.40(8) . . ?
C16 C4 C15 108.89(8) . . ?
C6 C5 N1 118.27(8) . . ?
C10 C5 N1 119.46(8) . . ?
C10 C5 C6 122.23(8) . . ?
C5 C6 C17 124.40(8) . . ?
C7 C6 C5 117.63(8) . . ?
C7 C6 C17 117.96(8) . . ?
C6 C7 H7 118.9(9) . . ?
C8 C7 C6 121.14(9) . . ?
C8 C7 H7 120.0(9) . . ?
C7 C8 H8 119.5(9) . . ?
C9 C8 C7 120.15(9) . . ?
C9 C8 H8 120.3(9) . . ?
C8 C9 C10 121.51(9) . . ?
C8 C9 H9 119.9(9) . . ?
C10 C9 H9 118.6(9) . . ?
C5 C10 C20 125.03(8) . . ?
C9 C10 C5 117.24(9) . . ?
C9 C10 C20 117.72(8) . . ?
C2 C11 H11A 110.0(8) . . ?
C2 C11 H11B 106.4(8) . . ?
C12 C11 C2 114.71(8) . . ?
C12 C11 H11A 108.6(9) . . ?
C12 C11 H11B 109.3(8) . . ?
H11A C11 H11B 107.6(12) . . ?
C11 C12 H12A 112.1(9) . . ?
C11 C12 H12B 110.5(9) . . ?
C11 C12 H12C 111.8(9) . . ?
H12A C12 H12B 107.6(12) . . ?
H12A C12 H12C 106.7(12) . . ?
H12B C12 H12C 107.9(12) . . ?
C2 C13 H13A 108.7(9) . . ?
C2 C13 H13B 108.7(9) . . ?
C14 C13 C2 114.10(8) . . ?
C14 C13 H13A 108.7(9) . . ?
C14 C13 H13B 109.7(9) . . ?
H13A C13 H13B 106.7(12) . . ?
C13 C14 H14A 111.1(9) . . ?
C13 C14 H14B 110.0(9) . . ?
C13 C14 H14C 112.4(9) . . ?
H14A C14 H14B 107.8(12) . . ?
H14A C14 H14C 108.1(12) . . ?
H14B C14 H14C 107.3(12) . . ?
C4 C15 H15A 112.3(9) . . ?
C4 C15 H15B 111.6(9) . . ?
C4 C15 H15C 108.8(8) . . ?
H15A C15 H15B 108.7(12) . . ?
H15A C15 H15C 106.0(12) . . ?
H15B C15 H15C 109.2(12) . . ?
C4 C16 H16A 108.0(9) . . ?
C4 C16 H16B 112.3(9) . . ?
C4 C16 H16C 110.6(9) . . ?
H16A C16 H16B 107.3(12) . . ?
H16A C16 H16C 107.4(12) . . ?
H16B C16 H16C 111.1(12) . . ?
C6 C17 C18 111.48(8) . . ?
C6 C17 C19 111.70(8) . . ?
C6 C17 H17 108.1(9) . . ?
C18 C17 H17 108.5(9) . . ?
C19 C17 C18 109.40(8) . . ?
C19 C17 H17 107.5(9) . . ?
C17 C18 H18A 112.1(9) . . ?
C17 C18 H18B 109.0(9) . . ?
C17 C18 H18C 111.1(9) . . ?
H18A C18 H18B 109.6(12) . . ?
H18A C18 H18C 107.7(12) . . ?
H18B C18 H18C 107.2(13) . . ?
C17 C19 H19A 111.5(9) . . ?
C17 C19 H19B 109.5(9) . . ?
C17 C19 H19C 111.3(9) . . ?
H19A C19 H19B 107.4(12) . . ?
H19A C19 H19C 108.7(12) . . ?
H19B C19 H19C 108.3(12) . . ?
C10 C20 C21 111.40(8) . . ?
C10 C20 C22 111.91(8) . . ?
C10 C20 H20 108.3(9) . . ?
C21 C20 H20 109.4(9) . . ?
C22 C20 C21 108.20(8) . . ?
C22 C20 H20 107.5(9) . . ?
C20 C21 H21A 111.2(9) . . ?
C20 C21 H21B 110.5(9) . . ?
C20 C21 H21C 111.8(9) . . ?
H21A C21 H21B 106.7(12) . . ?
H21A C21 H21C 108.2(12) . . ?
H21B C21 H21C 108.4(12) . . ?
C20 C22 H22A 111.8(9) . . ?
C20 C22 H22B 108.6(9) . . ?
C20 C22 H22C 110.8(9) . . ?
H22A C22 H22B 108.5(12) . . ?
H22A C22 H22C 109.1(12) . . ?
H22B C22 H22C 107.8(12) . . ?
F1 C23 F2 107.79(8) . . ?
F1 C23 F3 108.64(9) . . ?
F1 C23 S1 111.06(7) . . ?
F2 C23 S1 110.04(7) . . ?
F3 C23 F2 108.41(9) . . ?
F3 C23 S1 110.81(7) . . ?
O1 S1 C23 101.95(5) . . ?
O2 S1 C23 104.38(5) . . ?
O2 S1 O1 109.04(6) . . ?
O2 S1 O3 120.18(7) . . ?
O3 S1 C23 105.00(6) . . ?
O3 S1 O1 114.05(5) . . ?
S1 O1 B1 126.71(7) . . ?
_database_code_depnum_ccdc_archive 'CCDC 1001687'