# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_coden_Cambridge 222
loop_
_publ_author_name
'DeMott, Jessica'
'Surawatanawong, Panida'
'Barnett, Shoshanna'
'Chen, Chun-Hsing'
'Foxman, Bruce'
'Ozerov, Oleg'
_publ_contact_author_name 'Ozerov, Oleg'
_publ_contact_author_email ozerov@chem.tamu.edu
_publ_section_title
;
Experimental and Computational Exploration of (PNP)BF2,
a Boron Compound Supported By an Amido/Bis(Phosphine)
Pincer Ligand: Pentacoordination Elusive
;
# Attachment '- oz099_final_rev.cif'
data_oz099
_database_code_depnum_ccdc_archive 'CCDC 831094'
#TrackingRef '- oz099_final_rev.cif'
_audit_creation_date 11-05-02
_audit_creation_method CRYSTALS_ver_14.15
_oxford_structure_analysis_title 'OZ099_0m in P2(1)/c'
_chemical_name_systematic ?
_chemical_melting_point ?
# start Validation Reply Form: Two Alert B issues
_vrf_THETM01_oz099
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5022
RESPONSE: Crystals of this compound exhibited weak diffraction
patterns, with a sharp cutoff at ca. d = 1.0 A. Significant data
beyond that resolution was not attainable. Nonetheless, the structure
itself is unequivocally determined. There is no ambiguity regarding
atom types or stereochemistry.
;
_vrf_PLAT023_oz099
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 20.91 Deg.
RESPONSE: Crystals of this compound exhibited weak diffraction
patterns, with a sharp cutoff at ca. d = 1.0 A. Significant data
beyond that resolution was not attainable. Nonetheless, the structure
itself is unequivocally determined. There is no ambiguity regarding
atom types or stereochemistry.
;
# end Validation Reply Form
_cell_length_a 9.0396(7)
_cell_length_b 18.3375(13)
_cell_length_c 17.7856(13)
_cell_angle_alpha 90
_cell_angle_beta 94.796(4)
_cell_angle_gamma 90
_cell_volume 2937.9(4)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1 '
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C26 H41 B2 F6 N1 P2
# Dc = 1.28 Fooo = 1192.00 Mu = 2.02 M = 565.18
# Found Formula = C26 H41 B2 F6 N1 P2
# Dc = 1.28 FOOO = 1192.00 Mu = 2.02 M = 565.18
_chemical_formula_sum 'C26 H41 B2 F6 N1 P2'
_chemical_formula_moiety 'C26 H41 B2 F6 N1 P2'
_chemical_compound_source ?
_chemical_formula_weight 565.18
_cell_measurement_reflns_used 6591
_cell_measurement_theta_min 2
_cell_measurement_theta_max 21
_cell_measurement_temperature 120
_exptl_crystal_description 'prism fragment'
_exptl_crystal_colour colorless
_exptl_crystal_size_min 0.226
_exptl_crystal_size_mid 0.226
_exptl_crystal_size_max 0.283
_exptl_crystal_density_diffrn 1.278
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1192
_exptl_absorpt_coefficient_mu 0.202
# Sheldrick geometric approximatio 0.96 0.96
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_process_details 'Apex2 (Bruker AXS, 2006)'
_exptl_absorpt_correction_T_min 0.96
_exptl_absorpt_correction_T_max 0.96
_diffrn_measurement_device_type 'Bruker Kappa Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method '\f & \w scans'
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 120
_diffrn_reflns_number 21942
_reflns_number_total 3108
_diffrn_reflns_av_R_equivalents 0.044
# Number of reflections without Friedels Law is 3108
# Number of reflections with Friedels Law is 3108
# Theoretical number of reflections is about 3118
_diffrn_reflns_theta_min 1.598
_diffrn_reflns_theta_max 20.913
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 20.913
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min 0
_reflns_limit_k_max 18
_reflns_limit_l_min 0
_reflns_limit_l_max 17
_oxford_diffrn_Wilson_B_factor 1.85
_oxford_diffrn_Wilson_scale 3.95
_atom_sites_solution_primary Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.30
_refine_diff_density_max 0.42
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 3108
_refine_ls_number_restraints 0
_refine_ls_number_parameters 338
_oxford_refine_ls_R_factor_ref 0.0468
_refine_ls_wR_factor_ref 0.0892
_refine_ls_goodness_of_fit_ref 0.9978
_refine_ls_shift/su_max 0.0031110
_refine_ls_shift/su_mean 0.0000979
# The values computed from all data
_oxford_reflns_number_all 3108
_refine_ls_R_factor_all 0.0468
_refine_ls_wR_factor_all 0.0892
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 2592
_refine_ls_R_factor_gt 0.0364
_refine_ls_wR_factor_gt 0.0830
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 3.17P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
B1 B 0.3544(4) 0.5967(2) 0.2951(2) 0.0322 1.0000 Uani . . . . . .
B2 B 0.0544(4) 0.2819(2) 0.4454(2) 0.0310 1.0000 Uani . . . . . .
F1 F 0.48592(18) 0.58278(10) 0.33826(9) 0.0447 1.0000 Uani . . . . . .
F2 F 0.3337(2) 0.67199(9) 0.28865(10) 0.0446 1.0000 Uani . . . . . .
F3 F 0.0135(2) 0.26297(11) 0.51601(11) 0.0634 1.0000 Uani . . . . . .
F4 F 0.0159(2) 0.35360(10) 0.43171(11) 0.0503 1.0000 Uani . . . . . .
F5 F 0.2039(2) 0.27319(11) 0.44281(14) 0.0696 1.0000 Uani . . . . . .
F6 F -0.0242(2) 0.23779(10) 0.39240(10) 0.0541 1.0000 Uani . . . . . .
P1 P 0.18028(8) 0.54849(4) 0.33905(4) 0.0244 1.0000 Uani . . . . . .
P2 P 0.39982(8) 0.69482(4) 0.12008(4) 0.0254 1.0000 Uani . . . . . .
N1 N 0.3462(2) 0.55767(12) 0.21754(13) 0.0247 1.0000 Uani . . . . . .
C1 C 0.1552(3) 0.48330(15) 0.26459(15) 0.0228 1.0000 Uani . . . . . .
C2 C 0.0576(3) 0.42426(15) 0.25890(16) 0.0246 1.0000 Uani . . . . . .
C3 C 0.0519(3) 0.37737(15) 0.19730(16) 0.0263 1.0000 Uani . . . . . .
C4 C 0.1461(3) 0.39225(16) 0.14151(16) 0.0264 1.0000 Uani . . . . . .
C5 C 0.2443(3) 0.45014(16) 0.14577(16) 0.0257 1.0000 Uani . . . . . .
C6 C 0.2511(3) 0.49699(15) 0.20815(15) 0.0224 1.0000 Uani . . . . . .
C7 C 0.5188(3) 0.61773(15) 0.13624(15) 0.0236 1.0000 Uani . . . . . .
C8 C 0.6532(3) 0.61707(16) 0.10243(16) 0.0252 1.0000 Uani . . . . . .
C9 C 0.7463(3) 0.55765(16) 0.10736(16) 0.0246 1.0000 Uani . . . . . .
C10 C 0.7042(3) 0.49832(16) 0.14964(16) 0.0282 1.0000 Uani . . . . . .
C11 C 0.5741(3) 0.49844(16) 0.18486(16) 0.0293 1.0000 Uani . . . . . .
C12 C 0.4781(3) 0.55763(15) 0.17865(16) 0.0235 1.0000 Uani . . . . . .
C13 C -0.0519(3) 0.31333(16) 0.19268(17) 0.0344 1.0000 Uani . . . . . .
C14 C 0.8900(3) 0.55744(17) 0.07066(17) 0.0347 1.0000 Uani . . . . . .
C15 C 0.0161(3) 0.60613(16) 0.34154(16) 0.0296 1.0000 Uani . . . . . .
C16 C -0.1098(3) 0.56969(19) 0.37842(19) 0.0435 1.0000 Uani . . . . . .
C17 C -0.0335(4) 0.63105(18) 0.26164(18) 0.0429 1.0000 Uani . . . . . .
C18 C 0.2195(3) 0.50446(15) 0.42988(16) 0.0275 1.0000 Uani . . . . . .
C19 C 0.2611(3) 0.56315(17) 0.48913(17) 0.0370 1.0000 Uani . . . . . .
C20 C 0.3393(4) 0.44698(17) 0.42717(18) 0.0404 1.0000 Uani . . . . . .
C21 C 0.4878(3) 0.78033(15) 0.14972(17) 0.0297 1.0000 Uani . . . . . .
C22 C 0.5953(4) 0.77336(18) 0.21933(19) 0.0458 1.0000 Uani . . . . . .
C23 C 0.3652(4) 0.83566(16) 0.16077(19) 0.0405 1.0000 Uani . . . . . .
C24 C 0.3277(3) 0.69846(16) 0.02182(16) 0.0310 1.0000 Uani . . . . . .
C25 C 0.4416(4) 0.7165(2) -0.03395(18) 0.0468 1.0000 Uani . . . . . .
C26 C 0.2463(3) 0.62685(18) 0.00330(18) 0.0412 1.0000 Uani . . . . . .
H21 H -0.0034 0.4155 0.2975 0.0293 1.0000 Uiso R . . . . .
H41 H 0.1462 0.3619 0.1004 0.0321 1.0000 Uiso R . . . . .
H51 H 0.3085 0.4579 0.1077 0.0293 1.0000 Uiso R . . . . .
H81 H 0.6811 0.6578 0.0749 0.0294 1.0000 Uiso R . . . . .
H101 H 0.7652 0.4586 0.1557 0.0342 1.0000 Uiso R . . . . .
H111 H 0.5507 0.4586 0.2138 0.0339 1.0000 Uiso R . . . . .
H131 H -0.0234 0.2812 0.1523 0.0516 1.0000 Uiso R . . . . .
H132 H -0.1541 0.3291 0.1811 0.0519 1.0000 Uiso R . . . . .
H133 H -0.0467 0.2868 0.2398 0.0518 1.0000 Uiso R . . . . .
H141 H 0.8786 0.5343 0.0225 0.0524 1.0000 Uiso R . . . . .
H142 H 0.9660 0.5319 0.1012 0.0517 1.0000 Uiso R . . . . .
H143 H 0.9231 0.6062 0.0628 0.0520 1.0000 Uiso R . . . . .
H151 H 0.0474 0.6479 0.3725 0.0352 1.0000 Uiso R . . . . .
H161 H -0.1937 0.6028 0.3755 0.0644 1.0000 Uiso R . . . . .
H162 H -0.0803 0.5576 0.4299 0.0649 1.0000 Uiso R . . . . .
H163 H -0.1417 0.5256 0.3515 0.0641 1.0000 Uiso R . . . . .
H171 H -0.1134 0.6653 0.2645 0.0634 1.0000 Uiso R . . . . .
H172 H 0.0482 0.6536 0.2369 0.0638 1.0000 Uiso R . . . . .
H173 H -0.0709 0.5899 0.2318 0.0634 1.0000 Uiso R . . . . .
H181 H 0.1301 0.4806 0.4426 0.0322 1.0000 Uiso R . . . . .
H191 H 0.2839 0.5396 0.5377 0.0555 1.0000 Uiso R . . . . .
H192 H 0.1800 0.5984 0.4929 0.0557 1.0000 Uiso R . . . . .
H193 H 0.3488 0.5888 0.4762 0.0553 1.0000 Uiso R . . . . .
H201 H 0.3580 0.4245 0.4760 0.0601 1.0000 Uiso R . . . . .
H202 H 0.4295 0.4696 0.4122 0.0601 1.0000 Uiso R . . . . .
H203 H 0.3082 0.4095 0.3913 0.0603 1.0000 Uiso R . . . . .
H211 H 0.5416 0.7957 0.1072 0.0354 1.0000 Uiso R . . . . .
H221 H 0.6352 0.8200 0.2330 0.0681 1.0000 Uiso R . . . . .
H222 H 0.5472 0.7544 0.2620 0.0685 1.0000 Uiso R . . . . .
H223 H 0.6753 0.7406 0.2110 0.0687 1.0000 Uiso R . . . . .
H231 H 0.4098 0.8830 0.1681 0.0604 1.0000 Uiso R . . . . .
H232 H 0.2923 0.8372 0.1179 0.0604 1.0000 Uiso R . . . . .
H233 H 0.3180 0.8220 0.2053 0.0612 1.0000 Uiso R . . . . .
H241 H 0.2550 0.7366 0.0208 0.0363 1.0000 Uiso R . . . . .
H251 H 0.3903 0.7252 -0.0823 0.0694 1.0000 Uiso R . . . . .
H252 H 0.4995 0.7590 -0.0190 0.0697 1.0000 Uiso R . . . . .
H253 H 0.5081 0.6760 -0.0371 0.0696 1.0000 Uiso R . . . . .
H261 H 0.1889 0.6316 -0.0447 0.0611 1.0000 Uiso R . . . . .
H262 H 0.1806 0.6146 0.0424 0.0613 1.0000 Uiso R . . . . .
H263 H 0.3190 0.5876 0.0004 0.0613 1.0000 Uiso R . . . . .
H1 H 0.283(3) 0.6856(13) 0.1582(14) 0.027(7) 1.0000 Uiso . . . . . .
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 0.031(2) 0.032(3) 0.034(2) -0.0030(18) 0.0086(19) -0.0061(18)
B2 0.030(2) 0.028(2) 0.037(2) -0.0013(19) 0.0101(18) -0.0048(19)
F1 0.0269(11) 0.0711(14) 0.0364(11) -0.0083(10) 0.0037(9) -0.0128(10)
F2 0.0649(13) 0.0290(12) 0.0425(11) -0.0096(9) 0.0195(10) -0.0149(9)
F3 0.0752(15) 0.0729(15) 0.0418(13) 0.0096(11) 0.0024(11) -0.0292(12)
F4 0.0483(12) 0.0352(12) 0.0682(14) 0.0026(10) 0.0102(10) 0.0060(9)
F5 0.0342(13) 0.0505(14) 0.127(2) -0.0153(13) 0.0212(12) 0.0067(10)
F6 0.0654(14) 0.0523(13) 0.0448(12) -0.0135(10) 0.0056(10) -0.0121(11)
P1 0.0242(5) 0.0244(5) 0.0249(5) -0.0025(4) 0.0039(4) -0.0018(4)
P2 0.0219(5) 0.0231(5) 0.0316(5) -0.0003(4) 0.0047(4) -0.0010(4)
N1 0.0226(15) 0.0254(15) 0.0271(14) -0.0029(11) 0.0073(12) -0.0047(12)
C1 0.0226(17) 0.0226(18) 0.0234(17) 0.0015(14) 0.0028(14) -0.0009(15)
C2 0.0202(17) 0.0261(18) 0.0281(18) 0.0013(15) 0.0043(14) 0.0027(15)
C3 0.0275(18) 0.0213(18) 0.0294(19) 0.0032(15) -0.0021(15) 0.0021(15)
C4 0.0306(18) 0.0243(19) 0.0238(18) -0.0046(14) -0.0009(15) 0.0031(16)
C5 0.0254(18) 0.0288(19) 0.0236(18) 0.0021(15) 0.0063(14) 0.0016(16)
C6 0.0204(17) 0.0200(17) 0.0262(18) -0.0012(15) -0.0009(14) -0.0002(14)
C7 0.0223(18) 0.0225(18) 0.0259(17) -0.0015(14) 0.0015(14) -0.0032(14)
C8 0.0230(18) 0.0254(19) 0.0277(18) 0.0021(14) 0.0042(14) -0.0031(15)
C9 0.0220(18) 0.0276(19) 0.0239(17) -0.0034(15) 0.0012(14) -0.0021(16)
C10 0.0244(19) 0.0263(19) 0.0334(18) -0.0033(15) -0.0005(15) 0.0059(15)
C11 0.034(2) 0.0215(19) 0.0329(19) 0.0032(14) 0.0022(16) -0.0006(16)
C12 0.0202(18) 0.0251(19) 0.0252(17) -0.0046(14) 0.0014(14) -0.0037(15)
C13 0.040(2) 0.0265(19) 0.0371(19) -0.0025(15) 0.0043(16) -0.0055(16)
C14 0.0278(19) 0.041(2) 0.0361(19) -0.0028(16) 0.0069(15) 0.0006(16)
C15 0.0302(19) 0.0272(18) 0.0311(19) -0.0059(15) 0.0004(15) 0.0028(15)
C16 0.030(2) 0.054(2) 0.047(2) -0.0039(18) 0.0064(17) 0.0087(17)
C17 0.051(2) 0.035(2) 0.041(2) -0.0010(17) -0.0092(17) 0.0097(17)
C18 0.0230(17) 0.0280(18) 0.0311(18) 0.0012(15) 0.0005(14) -0.0004(15)
C19 0.037(2) 0.043(2) 0.0309(19) -0.0029(16) -0.0004(15) 0.0005(16)
C20 0.040(2) 0.037(2) 0.042(2) -0.0006(16) -0.0029(17) 0.0054(17)
C21 0.0287(18) 0.0249(18) 0.0358(19) -0.0020(14) 0.0050(15) -0.0031(15)
C22 0.043(2) 0.034(2) 0.058(2) -0.0020(17) -0.0135(19) -0.0065(17)
C23 0.044(2) 0.0265(19) 0.051(2) -0.0053(16) 0.0023(17) 0.0017(17)
C24 0.0265(18) 0.0316(19) 0.0343(19) -0.0009(15) -0.0002(15) 0.0033(15)
C25 0.043(2) 0.062(2) 0.036(2) 0.0081(18) 0.0006(17) -0.0060(19)
C26 0.036(2) 0.046(2) 0.041(2) -0.0108(17) -0.0003(16) -0.0039(17)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.5500(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 . F1 . 1.384(4) yes
B1 . F2 . 1.396(4) yes
B1 . P1 . 2.019(4) yes
B1 . N1 . 1.550(4) yes
B2 . F3 . 1.382(4) yes
B2 . F4 . 1.377(4) yes
B2 . F5 . 1.365(4) yes
B2 . F6 . 1.391(4) yes
P1 . C1 . 1.784(3) yes
P1 . C15 . 1.825(3) yes
P1 . C18 . 1.814(3) yes
P2 . C7 . 1.785(3) yes
P2 . C21 . 1.816(3) yes
P2 . C24 . 1.815(3) yes
P2 . H1 . 1.31(3) no
N1 . C6 . 1.407(3) yes
N1 . C12 . 1.428(3) yes
C1 . C2 . 1.395(4) yes
C1 . C6 . 1.403(4) yes
C2 . C3 . 1.390(4) yes
C2 . H21 . 0.930 no
C3 . C4 . 1.388(4) yes
C3 . C13 . 1.501(4) yes
C4 . C5 . 1.382(4) yes
C4 . H41 . 0.918 no
C5 . C6 . 1.401(4) yes
C5 . H51 . 0.939 no
C7 . C8 . 1.400(4) yes
C7 . C12 . 1.402(4) yes
C8 . C9 . 1.375(4) yes
C8 . H81 . 0.938 no
C9 . C10 . 1.393(4) yes
C9 . C14 . 1.502(4) yes
C10 . C11 . 1.378(4) yes
C10 . H101 . 0.914 no
C11 . C12 . 1.389(4) yes
C11 . H111 . 0.929 no
C13 . H131 . 0.980 no
C13 . H132 . 0.973 no
C13 . H133 . 0.966 no
C14 . H141 . 0.953 no
C14 . H142 . 0.962 no
C14 . H143 . 0.957 no
C15 . C16 . 1.516(4) yes
C15 . C17 . 1.524(4) yes
C15 . H151 . 0.971 no
C16 . H161 . 0.970 no
C16 . H162 . 0.957 no
C16 . H163 . 0.971 no
C17 . H171 . 0.962 no
C17 . H172 . 0.982 no
C17 . H173 . 0.967 no
C18 . C19 . 1.531(4) yes
C18 . C20 . 1.515(4) yes
C18 . H181 . 0.963 no
C19 . H191 . 0.972 no
C19 . H192 . 0.984 no
C19 . H193 . 0.966 no
C20 . H201 . 0.963 no
C20 . H202 . 0.971 no
C20 . H203 . 0.964 no
C21 . C22 . 1.514(4) yes
C21 . C23 . 1.527(4) yes
C21 . H211 . 0.975 no
C22 . H221 . 0.952 no
C22 . H222 . 0.970 no
C22 . H223 . 0.961 no
C23 . H231 . 0.962 no
C23 . H232 . 0.966 no
C23 . H233 . 0.964 no
C24 . C25 . 1.525(4) yes
C24 . C26 . 1.528(4) yes
C24 . H241 . 0.958 no
C25 . H251 . 0.956 no
C25 . H252 . 0.963 no
C25 . H253 . 0.959 no
C26 . H261 . 0.965 no
C26 . H262 . 0.977 no
C26 . H263 . 0.979 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . B1 . F2 . 109.3(3) yes
F1 . B1 . P1 . 111.4(2) yes
F2 . B1 . P1 . 111.2(2) yes
F1 . B1 . N1 . 112.5(3) yes
F2 . B1 . N1 . 112.8(3) yes
P1 . B1 . N1 . 99.3(2) yes
F3 . B2 . F4 . 108.5(3) yes
F3 . B2 . F5 . 110.0(3) yes
F4 . B2 . F5 . 110.0(3) yes
F3 . B2 . F6 . 108.0(3) yes
F4 . B2 . F6 . 109.1(3) yes
F5 . B2 . F6 . 111.1(3) yes
B1 . P1 . C1 . 93.47(14) yes
B1 . P1 . C15 . 114.67(15) yes
C1 . P1 . C15 . 110.66(13) yes
B1 . P1 . C18 . 116.06(15) yes
C1 . P1 . C18 . 111.46(13) yes
C15 . P1 . C18 . 109.56(13) yes
C7 . P2 . C21 . 113.19(13) yes
C7 . P2 . C24 . 110.33(14) yes
C21 . P2 . C24 . 111.17(14) yes
C7 . P2 . H1 . 108.3(11) no
C21 . P2 . H1 . 108.2(11) no
C24 . P2 . H1 . 105.3(10) no
B1 . N1 . C6 . 117.0(2) yes
B1 . N1 . C12 . 116.8(2) yes
C6 . N1 . C12 . 117.9(2) yes
P1 . C1 . C2 . 127.9(2) yes
P1 . C1 . C6 . 111.3(2) yes
C2 . C1 . C6 . 120.8(3) yes
C1 . C2 . C3 . 121.2(3) yes
C1 . C2 . H21 . 119.4 no
C3 . C2 . H21 . 119.3 no
C2 . C3 . C4 . 117.2(3) yes
C2 . C3 . C13 . 120.6(3) yes
C4 . C3 . C13 . 122.2(3) yes
C3 . C4 . C5 . 122.8(3) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 117.7 no
C4 . C5 . C6 . 120.0(3) yes
C4 . C5 . H51 . 120.7 no
C6 . C5 . H51 . 119.3 no
N1 . C6 . C1 . 117.7(2) yes
N1 . C6 . C5 . 124.4(3) yes
C1 . C6 . C5 . 117.9(3) yes
P2 . C7 . C8 . 118.1(2) yes
P2 . C7 . C12 . 121.8(2) yes
C8 . C7 . C12 . 120.0(3) yes
C7 . C8 . C9 . 121.9(3) yes
C7 . C8 . H81 . 119.8 no
C9 . C8 . H81 . 118.3 no
C8 . C9 . C10 . 117.4(3) yes
C8 . C9 . C14 . 121.4(3) yes
C10 . C9 . C14 . 121.2(3) yes
C9 . C10 . C11 . 121.7(3) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 118.5 no
C10 . C11 . C12 . 121.1(3) yes
C10 . C11 . H111 . 119.6 no
C12 . C11 . H111 . 119.3 no
N1 . C12 . C7 . 121.9(2) yes
N1 . C12 . C11 . 120.3(3) yes
C7 . C12 . C11 . 117.8(3) yes
C3 . C13 . H131 . 108.0 no
C3 . C13 . H132 . 110.9 no
H131 . C13 . H132 . 109.0 no
C3 . C13 . H133 . 111.2 no
H131 . C13 . H133 . 109.6 no
H132 . C13 . H133 . 108.0 no
C9 . C14 . H141 . 111.1 no
C9 . C14 . H142 . 111.0 no
H141 . C14 . H142 . 108.0 no
C9 . C14 . H143 . 110.7 no
H141 . C14 . H143 . 107.2 no
H142 . C14 . H143 . 108.7 no
P1 . C15 . C16 . 113.4(2) yes
P1 . C15 . C17 . 109.1(2) yes
C16 . C15 . C17 . 111.3(3) yes
P1 . C15 . H151 . 105.7 no
C16 . C15 . H151 . 107.2 no
C17 . C15 . H151 . 109.9 no
C15 . C16 . H161 . 108.3 no
C15 . C16 . H162 . 110.9 no
H161 . C16 . H162 . 110.5 no
C15 . C16 . H163 . 110.9 no
H161 . C16 . H163 . 107.3 no
H162 . C16 . H163 . 109.0 no
C15 . C17 . H171 . 108.1 no
C15 . C17 . H172 . 111.7 no
H171 . C17 . H172 . 110.1 no
C15 . C17 . H173 . 109.8 no
H171 . C17 . H173 . 108.0 no
H172 . C17 . H173 . 109.0 no
P1 . C18 . C19 . 108.6(2) yes
P1 . C18 . C20 . 111.6(2) yes
C19 . C18 . C20 . 112.1(2) yes
P1 . C18 . H181 . 107.8 no
C19 . C18 . H181 . 108.7 no
C20 . C18 . H181 . 107.9 no
C18 . C19 . H191 . 108.7 no
C18 . C19 . H192 . 111.6 no
H191 . C19 . H192 . 109.6 no
C18 . C19 . H193 . 109.7 no
H191 . C19 . H193 . 108.1 no
H192 . C19 . H193 . 109.2 no
C18 . C20 . H201 . 109.9 no
C18 . C20 . H202 . 109.3 no
H201 . C20 . H202 . 110.0 no
C18 . C20 . H203 . 110.3 no
H201 . C20 . H203 . 108.1 no
H202 . C20 . H203 . 109.2 no
P2 . C21 . C22 . 113.6(2) yes
P2 . C21 . C23 . 107.8(2) yes
C22 . C21 . C23 . 112.0(3) yes
P2 . C21 . H211 . 105.0 no
C22 . C21 . H211 . 109.3 no
C23 . C21 . H211 . 108.8 no
C21 . C22 . H221 . 109.7 no
C21 . C22 . H222 . 111.7 no
H221 . C22 . H222 . 107.9 no
C21 . C22 . H223 . 111.5 no
H221 . C22 . H223 . 109.1 no
H222 . C22 . H223 . 106.7 no
C21 . C23 . H231 . 108.5 no
C21 . C23 . H232 . 111.8 no
H231 . C23 . H232 . 109.4 no
C21 . C23 . H233 . 108.0 no
H231 . C23 . H233 . 109.4 no
H232 . C23 . H233 . 109.7 no
P2 . C24 . C25 . 115.3(2) yes
P2 . C24 . C26 . 107.7(2) yes
C25 . C24 . C26 . 112.7(3) yes
P2 . C24 . H241 . 103.6 no
C25 . C24 . H241 . 109.2 no
C26 . C24 . H241 . 107.8 no
C24 . C25 . H251 . 108.6 no
C24 . C25 . H252 . 112.1 no
H251 . C25 . H252 . 109.0 no
C24 . C25 . H253 . 109.4 no
H251 . C25 . H253 . 109.6 no
H252 . C25 . H253 . 108.2 no
C24 . C26 . H261 . 109.1 no
C24 . C26 . H262 . 110.7 no
H261 . C26 . H262 . 109.7 no
C24 . C26 . H263 . 109.3 no
H261 . C26 . H263 . 109.4 no
H262 . C26 . H263 . 108.6 no
_iucr_refine_instruction_details_constraints
;
#
# Punched on 02/05/11 at 11:50:58
#
#LIST 12
BLOCK SCALE X'S, U'S H(1,X'S,U[ISO])
RIDE C ( 2,X'S) H ( 21,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S)
RIDE C ( 8,X'S) H ( 81,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 11,X'S) H ( 111,X'S)
RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S)
RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) H ( 163,X'S)
RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) H ( 173,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S)
RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 221,X'S) H ( 222,X'S) H ( 223,X'S)
RIDE C ( 23,X'S) H ( 231,X'S) H ( 232,X'S) H ( 233,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S) H ( 252,X'S) H ( 253,X'S)
RIDE C ( 26,X'S) H ( 261,X'S) H ( 262,X'S) H ( 263,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 02/05/11 at 11:50:58
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
# Attachment '- oz122_final.cif'
data_oz122
_database_code_depnum_ccdc_archive 'CCDC 831095'
#TrackingRef '- oz122_final.cif'
_audit_creation_date 11-01-17
_audit_creation_method CRYSTALS_ver_14.15
_oxford_structure_analysis_title 'OZ122_0ma in P2(1)/c'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 13.715(4)
_cell_length_b 15.645(4)
_cell_length_c 12.476(3)
_cell_angle_alpha 90
_cell_angle_beta 103.442(4)
_cell_angle_gamma 90
_cell_volume 2603.6(12)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1 '
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C26 H40 B1 F2 N1 P2
# Dc = 1.22 Fooo = 1024.00 Mu = 1.96 M = 477.36
# Found Formula = C26 H40 B1 F2 N1 P2
# Dc = 1.22 FOOO = 1024.00 Mu = 1.96 M = 477.36
_chemical_formula_sum 'C26 H40 B1 F2 N1 P2'
_chemical_formula_moiety 'C26 H40 B1 F2 N1 P2'
_chemical_compound_source ?
_chemical_formula_weight 477.36
_cell_measurement_reflns_used 3474
_cell_measurement_theta_min 2
_cell_measurement_theta_max 26
_cell_measurement_temperature 120
_exptl_crystal_description acicular
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.111
_exptl_crystal_size_mid 0.243
_exptl_crystal_size_max 0.409
_exptl_crystal_density_diffrn 1.218
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1024
_exptl_absorpt_coefficient_mu 0.196
# Sheldrick geometric approximatio 0.95 0.98
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_process_details 'Apex2 (Bruker AXS, 2006)'
_exptl_absorpt_correction_T_min 0.95
_exptl_absorpt_correction_T_max 0.98
_diffrn_measurement_device_type 'Bruker Kappa Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method '\f & \w scans'
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 120
_diffrn_reflns_number 26561
_reflns_number_total 5110
_diffrn_reflns_av_R_equivalents 0.128
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 5110
# Theoretical number of reflections is about 10245
_diffrn_reflns_theta_min 1.527
_diffrn_reflns_theta_max 26.008
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.008
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_reflns_limit_h_min -16
_reflns_limit_h_max 16
_reflns_limit_k_min 0
_reflns_limit_k_max 19
_reflns_limit_l_min 0
_reflns_limit_l_max 15
_oxford_diffrn_Wilson_B_factor 1.26
_oxford_diffrn_Wilson_scale 4.33
_atom_sites_solution_primary Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.67
_refine_diff_density_max 0.65
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 5110
_refine_ls_number_restraints 0
_refine_ls_number_parameters 289
_oxford_refine_ls_R_factor_ref 0.0834
_refine_ls_wR_factor_ref 0.1584
_refine_ls_goodness_of_fit_ref 0.9642
_refine_ls_shift/su_max 0.0022219
_refine_ls_shift/su_mean 0.0004628
# The values computed from all data
_oxford_reflns_number_all 5110
_refine_ls_R_factor_all 0.0834
_refine_ls_wR_factor_all 0.1584
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 3497
_refine_ls_R_factor_gt 0.0515
_refine_ls_wR_factor_gt 0.1241
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
9.16 13.6 6.79 1.89
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.34985(6) 0.45918(5) 0.82517(6) 0.0166 1.0000 Uani . . . . . .
P2 P 0.09436(6) 0.65429(5) 0.93257(6) 0.0162 1.0000 Uani . . . . . .
F1 F 0.02380(15) 0.50561(13) 0.79690(16) 0.0274 1.0000 Uani . . . . . .
F2 F -0.00651(14) 0.63451(14) 0.71098(16) 0.0279 1.0000 Uani . . . . . .
N1 N 0.16818(18) 0.58438(16) 0.7686(2) 0.0155 1.0000 Uani . . . . . .
C1 C 0.4204(3) 0.8569(2) 0.9847(3) 0.0258 1.0000 Uani . . . . . .
C2 C 0.3543(2) 0.7858(2) 0.9267(3) 0.0184 1.0000 Uani . . . . . .
C3 C 0.2676(2) 0.76145(19) 0.9587(2) 0.0175 1.0000 Uani . . . . . .
C4 C 0.2089(2) 0.69372(19) 0.9062(2) 0.0164 1.0000 Uani . . . . . .
C5 C 0.2338(2) 0.64936(19) 0.8179(2) 0.0150 1.0000 Uani . . . . . .
C6 C 0.3204(2) 0.67431(19) 0.7856(3) 0.0183 1.0000 Uani . . . . . .
C7 C 0.3791(2) 0.7408(2) 0.8400(3) 0.0183 1.0000 Uani . . . . . .
C8 C 0.1849(3) 0.5122(2) 1.0431(3) 0.0251 1.0000 Uani . . . . . .
C9 C 0.1198(2) 0.5891(2) 1.0578(3) 0.0200 1.0000 Uani . . . . . .
C10 C 0.1660(3) 0.6404(2) 1.1606(3) 0.0276 1.0000 Uani . . . . . .
C11 C -0.0771(3) 0.7160(2) 0.9899(3) 0.0307 1.0000 Uani . . . . . .
C12 C 0.0170(2) 0.7453(2) 0.9551(3) 0.0214 1.0000 Uani . . . . . .
C13 C -0.0085(3) 0.8041(2) 0.8546(3) 0.0274 1.0000 Uani . . . . . .
C14 C 0.2535(3) 0.4280(2) 0.3832(3) 0.0265 1.0000 Uani . . . . . .
C15 C 0.2281(2) 0.46393(19) 0.4855(2) 0.0179 1.0000 Uani . . . . . .
C16 C 0.1411(2) 0.5113(2) 0.4795(3) 0.0188 1.0000 Uani . . . . . .
C17 C 0.1226(2) 0.54914(19) 0.5735(3) 0.0177 1.0000 Uani . . . . . .
C18 C 0.1886(2) 0.53926(18) 0.6764(2) 0.0153 1.0000 Uani . . . . . .
C19 C 0.2731(2) 0.48604(19) 0.6862(2) 0.0156 1.0000 Uani . . . . . .
C20 C 0.2912(2) 0.4511(2) 0.5893(3) 0.0177 1.0000 Uani . . . . . .
C21 C 0.5225(3) 0.5096(3) 0.7640(3) 0.0332 1.0000 Uani . . . . . .
C22 C 0.4712(2) 0.4289(2) 0.7938(3) 0.0214 1.0000 Uani . . . . . .
C23 C 0.5395(2) 0.3853(2) 0.8942(3) 0.0281 1.0000 Uani . . . . . .
C24 C 0.3004(3) 0.2832(2) 0.7633(3) 0.0350 1.0000 Uani . . . . . .
C25 C 0.2889(2) 0.3540(2) 0.8435(3) 0.0238 1.0000 Uani . . . . . .
C26 C 0.3204(3) 0.3237(2) 0.9641(3) 0.0281 1.0000 Uani . . . . . .
B1 B 0.0619(3) 0.5868(2) 0.7882(3) 0.0184 1.0000 Uani . . . . . .
H13 H 0.4561 0.8844 0.9370 0.0396 1.0000 Uiso R . . . . .
H12 H 0.3818 0.8977 1.0095 0.0400 1.0000 Uiso R . . . . .
H11 H 0.4684 0.8354 1.0471 0.0400 1.0000 Uiso R . . . . .
H31 H 0.2488 0.7896 1.0182 0.0204 1.0000 Uiso R . . . . .
H61 H 0.3391 0.6483 0.7259 0.0216 1.0000 Uiso R . . . . .
H71 H 0.4372 0.7562 0.8141 0.0199 1.0000 Uiso R . . . . .
H83 H 0.2007 0.4767 1.1090 0.0381 1.0000 Uiso R . . . . .
H82 H 0.2468 0.5302 1.0309 0.0383 1.0000 Uiso R . . . . .
H81 H 0.1526 0.4758 0.9821 0.0371 1.0000 Uiso R . . . . .
H91 H 0.0547 0.5673 1.0658 0.0238 1.0000 Uiso R . . . . .
H103 H 0.1725 0.6026 1.2215 0.0401 1.0000 Uiso R . . . . .
H102 H 0.1248 0.6883 1.1689 0.0414 1.0000 Uiso R . . . . .
H101 H 0.2315 0.6601 1.1544 0.0408 1.0000 Uiso R . . . . .
H111 H -0.1125 0.7663 1.0039 0.0457 1.0000 Uiso R . . . . .
H112 H -0.0588 0.6813 1.0572 0.0457 1.0000 Uiso R . . . . .
H113 H -0.1208 0.6828 0.9312 0.0450 1.0000 Uiso R . . . . .
H121 H 0.0592 0.7766 1.0168 0.0254 1.0000 Uiso R . . . . .
H133 H -0.0448 0.8531 0.8723 0.0410 1.0000 Uiso R . . . . .
H132 H 0.0515 0.8252 0.8353 0.0403 1.0000 Uiso R . . . . .
H131 H -0.0507 0.7745 0.7939 0.0410 1.0000 Uiso R . . . . .
H143 H 0.3118 0.3916 0.4006 0.0398 1.0000 Uiso R . . . . .
H142 H 0.2676 0.4729 0.3372 0.0404 1.0000 Uiso R . . . . .
H141 H 0.1986 0.3952 0.3421 0.0404 1.0000 Uiso R . . . . .
H161 H 0.0960 0.5175 0.4107 0.0212 1.0000 Uiso R . . . . .
H171 H 0.0642 0.5822 0.5681 0.0201 1.0000 Uiso R . . . . .
H201 H 0.3493 0.4181 0.5940 0.0217 1.0000 Uiso R . . . . .
H213 H 0.5854 0.4950 0.7490 0.0488 1.0000 Uiso R . . . . .
H212 H 0.5330 0.5508 0.8246 0.0492 1.0000 Uiso R . . . . .
H211 H 0.4803 0.5361 0.6993 0.0483 1.0000 Uiso R . . . . .
H221 H 0.4602 0.3894 0.7322 0.0259 1.0000 Uiso R . . . . .
H233 H 0.6052 0.3773 0.8781 0.0442 1.0000 Uiso R . . . . .
H232 H 0.5462 0.4211 0.9588 0.0438 1.0000 Uiso R . . . . .
H231 H 0.5118 0.3294 0.9075 0.0434 1.0000 Uiso R . . . . .
H241 H 0.2614 0.2332 0.7726 0.0520 1.0000 Uiso R . . . . .
H242 H 0.3713 0.2667 0.7735 0.0530 1.0000 Uiso R . . . . .
H243 H 0.2789 0.3028 0.6858 0.0519 1.0000 Uiso R . . . . .
H251 H 0.2168 0.3677 0.8289 0.0272 1.0000 Uiso R . . . . .
H263 H 0.2802 0.2742 0.9754 0.0423 1.0000 Uiso R . . . . .
H262 H 0.3105 0.3704 1.0135 0.0428 1.0000 Uiso R . . . . .
H261 H 0.3918 0.3081 0.9848 0.0427 1.0000 Uiso 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
P1 0.0137(4) 0.0188(4) 0.0163(4) 0.0008(3) 0.0015(3) 0.0020(3)
P2 0.0137(4) 0.0174(4) 0.0184(4) -0.0032(3) 0.0053(3) -0.0025(3)
F1 0.0275(10) 0.0273(11) 0.0300(10) -0.0103(8) 0.0119(8) -0.0127(8)
F2 0.0178(9) 0.0403(12) 0.0236(10) -0.0050(9) 0.0007(8) 0.0073(8)
N1 0.0112(12) 0.0169(12) 0.0173(12) -0.0033(10) 0.0011(10) -0.0024(10)
C1 0.0234(17) 0.0231(17) 0.0311(18) -0.0059(14) 0.0071(14) -0.0070(14)
C2 0.0155(15) 0.0175(15) 0.0199(15) -0.0007(12) -0.0009(12) -0.0004(12)
C3 0.0171(15) 0.0164(14) 0.0176(14) -0.0022(12) 0.0011(12) 0.0012(12)
C4 0.0122(14) 0.0191(15) 0.0185(14) 0.0015(12) 0.0046(11) 0.0006(12)
C5 0.0120(13) 0.0142(14) 0.0163(14) 0.0025(11) -0.0016(11) -0.0008(11)
C6 0.0198(15) 0.0165(15) 0.0193(15) 0.0017(12) 0.0062(12) 0.0015(12)
C7 0.0172(15) 0.0176(15) 0.0199(15) 0.0029(12) 0.0041(12) -0.0001(12)
C8 0.0280(18) 0.0246(17) 0.0229(16) 0.0016(13) 0.0061(14) 0.0017(14)
C9 0.0180(15) 0.0217(16) 0.0223(16) 0.0016(13) 0.0092(12) -0.0037(12)
C10 0.0334(19) 0.0294(18) 0.0195(16) -0.0011(13) 0.0051(14) 0.0013(15)
C11 0.0230(18) 0.0308(19) 0.045(2) -0.0036(16) 0.0211(16) 0.0003(14)
C12 0.0170(15) 0.0215(16) 0.0278(17) -0.0063(13) 0.0092(13) 0.0025(13)
C13 0.0245(17) 0.0235(17) 0.0321(19) -0.0001(14) 0.0021(14) 0.0007(14)
C14 0.0238(17) 0.0356(19) 0.0205(16) -0.0028(14) 0.0063(13) 0.0057(14)
C15 0.0197(15) 0.0146(14) 0.0187(15) -0.0023(12) 0.0032(12) -0.0004(12)
C16 0.0206(15) 0.0190(15) 0.0156(14) 0.0010(12) 0.0017(12) -0.0017(12)
C17 0.0150(14) 0.0178(15) 0.0197(15) -0.0003(12) 0.0029(12) 0.0002(12)
C18 0.0181(14) 0.0128(13) 0.0157(14) 0.0001(11) 0.0052(11) -0.0014(11)
C19 0.0138(14) 0.0151(14) 0.0169(14) 0.0018(11) 0.0015(11) 0.0018(11)
C20 0.0154(14) 0.0176(15) 0.0207(15) 0.0002(12) 0.0054(12) 0.0005(12)
C21 0.0183(17) 0.044(2) 0.037(2) 0.0081(17) 0.0064(15) -0.0045(16)
C22 0.0153(15) 0.0289(17) 0.0183(15) 0.0006(13) 0.0004(12) 0.0025(13)
C23 0.0181(16) 0.037(2) 0.0269(18) 0.0071(16) 0.0000(13) 0.0081(14)
C24 0.046(2) 0.0230(18) 0.032(2) 0.0036(15) -0.0001(17) -0.0092(16)
C25 0.0217(16) 0.0233(17) 0.0254(17) 0.0071(14) 0.0031(13) 0.0002(13)
C26 0.0249(17) 0.0333(19) 0.0273(18) 0.0143(15) 0.0087(14) 0.0033(15)
B1 0.0136(16) 0.0218(18) 0.0196(17) -0.0039(14) 0.0038(13) -0.0019(13)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.16142(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 . C19 . 1.855(3) yes
P1 . C22 . 1.857(3) yes
P1 . C25 . 1.883(3) yes
P2 . C4 . 1.788(3) yes
P2 . C9 . 1.830(3) yes
P2 . C12 . 1.835(3) yes
P2 . B1 . 2.046(4) yes
F1 . B1 . 1.388(4) yes
F2 . B1 . 1.394(4) yes
N1 . C5 . 1.401(4) yes
N1 . C18 . 1.432(4) yes
N1 . B1 . 1.534(4) yes
C1 . C2 . 1.509(4) yes
C1 . H13 . 0.957 no
C1 . H12 . 0.928 no
C1 . H11 . 0.955 no
C2 . C3 . 1.392(4) yes
C2 . C7 . 1.397(4) yes
C3 . C4 . 1.399(4) yes
C3 . H31 . 0.949 no
C4 . C5 . 1.409(4) yes
C5 . C6 . 1.397(4) yes
C6 . C7 . 1.392(4) yes
C6 . H61 . 0.936 no
C7 . H71 . 0.958 no
C8 . C9 . 1.533(4) yes
C8 . H83 . 0.974 no
C8 . H82 . 0.940 no
C8 . H81 . 0.971 no
C9 . C10 . 1.521(5) yes
C9 . H91 . 0.982 no
C10 . H103 . 0.951 no
C10 . H102 . 0.958 no
C10 . H101 . 0.970 no
C11 . C12 . 1.525(4) yes
C11 . H111 . 0.961 no
C11 . H112 . 0.982 no
C11 . H113 . 0.981 no
C12 . C13 . 1.529(5) yes
C12 . H121 . 0.981 no
C13 . H133 . 0.968 no
C13 . H132 . 0.967 no
C13 . H131 . 0.958 no
C14 . C15 . 1.508(4) yes
C14 . H143 . 0.964 no
C14 . H142 . 0.955 no
C14 . H141 . 0.957 no
C15 . C16 . 1.392(4) yes
C15 . C20 . 1.395(4) yes
C16 . C17 . 1.388(4) yes
C16 . H161 . 0.939 no
C17 . C18 . 1.396(4) yes
C17 . H171 . 0.943 no
C18 . C19 . 1.410(4) yes
C19 . C20 . 1.400(4) yes
C20 . H201 . 0.941 no
C21 . C22 . 1.533(5) yes
C21 . H213 . 0.952 no
C21 . H212 . 0.978 no
C21 . H211 . 0.970 no
C22 . C23 . 1.538(4) yes
C22 . H221 . 0.971 no
C23 . H233 . 0.976 no
C23 . H232 . 0.968 no
C23 . H231 . 0.983 no
C24 . C25 . 1.525(5) yes
C24 . H241 . 0.970 no
C24 . H242 . 0.985 no
C24 . H243 . 0.991 no
C25 . C26 . 1.540(4) yes
C25 . H251 . 0.987 no
C26 . H263 . 0.980 no
C26 . H262 . 0.985 no
C26 . H261 . 0.984 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 . P1 . C22 . 101.68(14) yes
C19 . P1 . C25 . 98.07(14) yes
C22 . P1 . C25 . 104.31(15) yes
C4 . P2 . C9 . 110.38(14) yes
C4 . P2 . C12 . 108.93(14) yes
C9 . P2 . C12 . 107.70(15) yes
C4 . P2 . B1 . 92.10(14) yes
C9 . P2 . B1 . 115.05(15) yes
C12 . P2 . B1 . 121.31(15) yes
C5 . N1 . C18 . 119.0(2) yes
C5 . N1 . B1 . 116.7(2) yes
C18 . N1 . B1 . 120.7(2) yes
C2 . C1 . H13 . 111.7 no
C2 . C1 . H12 . 110.0 no
H13 . C1 . H12 . 108.1 no
C2 . C1 . H11 . 110.8 no
H13 . C1 . H11 . 108.0 no
H12 . C1 . H11 . 108.0 no
C1 . C2 . C3 . 121.4(3) yes
C1 . C2 . C7 . 121.0(3) yes
C3 . C2 . C7 . 117.5(3) yes
C2 . C3 . C4 . 120.6(3) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 119.1 no
P2 . C4 . C3 . 127.6(2) yes
P2 . C4 . C5 . 110.9(2) yes
C3 . C4 . C5 . 121.5(3) yes
C4 . C5 . N1 . 117.0(3) yes
C4 . C5 . C6 . 117.7(3) yes
N1 . C5 . C6 . 125.4(3) yes
C5 . C6 . C7 . 120.2(3) yes
C5 . C6 . H61 . 121.1 no
C7 . C6 . H61 . 118.6 no
C2 . C7 . C6 . 122.4(3) yes
C2 . C7 . H71 . 120.4 no
C6 . C7 . H71 . 117.1 no
C9 . C8 . H83 . 111.7 no
C9 . C8 . H82 . 111.0 no
H83 . C8 . H82 . 106.0 no
C9 . C8 . H81 . 112.4 no
H83 . C8 . H81 . 107.3 no
H82 . C8 . H81 . 108.2 no
C8 . C9 . P2 . 109.6(2) yes
C8 . C9 . C10 . 112.0(3) yes
P2 . C9 . C10 . 112.6(2) yes
C8 . C9 . H91 . 108.0 no
P2 . C9 . H91 . 106.4 no
C10 . C9 . H91 . 107.9 no
C9 . C10 . H103 . 106.8 no
C9 . C10 . H102 . 111.4 no
H103 . C10 . H102 . 110.4 no
C9 . C10 . H101 . 108.2 no
H103 . C10 . H101 . 110.1 no
H102 . C10 . H101 . 109.9 no
C12 . C11 . H111 . 107.6 no
C12 . C11 . H112 . 110.1 no
H111 . C11 . H112 . 109.7 no
C12 . C11 . H113 . 110.9 no
H111 . C11 . H113 . 108.8 no
H112 . C11 . H113 . 109.7 no
C11 . C12 . P2 . 111.6(2) yes
C11 . C12 . C13 . 111.5(3) yes
P2 . C12 . C13 . 111.8(2) yes
C11 . C12 . H121 . 108.1 no
P2 . C12 . H121 . 104.6 no
C13 . C12 . H121 . 108.9 no
C12 . C13 . H133 . 108.7 no
C12 . C13 . H132 . 111.3 no
H133 . C13 . H132 . 107.5 no
C12 . C13 . H131 . 109.8 no
H133 . C13 . H131 . 108.4 no
H132 . C13 . H131 . 111.1 no
C15 . C14 . H143 . 111.9 no
C15 . C14 . H142 . 110.7 no
H143 . C14 . H142 . 107.3 no
C15 . C14 . H141 . 110.2 no
H143 . C14 . H141 . 108.1 no
H142 . C14 . H141 . 108.5 no
C14 . C15 . C16 . 121.2(3) yes
C14 . C15 . C20 . 121.1(3) yes
C16 . C15 . C20 . 117.7(3) yes
C15 . C16 . C17 . 120.3(3) yes
C15 . C16 . H161 . 118.5 no
C17 . C16 . H161 . 121.2 no
C16 . C17 . C18 . 121.5(3) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 119.0 no
N1 . C18 . C17 . 118.6(3) yes
N1 . C18 . C19 . 122.1(3) yes
C17 . C18 . C19 . 119.3(3) yes
P1 . C19 . C18 . 119.5(2) yes
P1 . C19 . C20 . 122.9(2) yes
C18 . C19 . C20 . 117.5(3) yes
C19 . C20 . C15 . 123.4(3) yes
C19 . C20 . H201 . 118.5 no
C15 . C20 . H201 . 118.1 no
C22 . C21 . H213 . 109.8 no
C22 . C21 . H212 . 110.4 no
H213 . C21 . H212 . 109.5 no
C22 . C21 . H211 . 109.6 no
H213 . C21 . H211 . 109.3 no
H212 . C21 . H211 . 108.3 no
C21 . C22 . P1 . 109.0(2) yes
C21 . C22 . C23 . 109.6(3) yes
P1 . C22 . C23 . 110.4(2) yes
C21 . C22 . H221 . 109.1 no
P1 . C22 . H221 . 110.3 no
C23 . C22 . H221 . 108.5 no
C22 . C23 . H233 . 107.9 no
C22 . C23 . H232 . 110.0 no
H233 . C23 . H232 . 109.5 no
C22 . C23 . H231 . 110.1 no
H233 . C23 . H231 . 109.4 no
H232 . C23 . H231 . 109.8 no
C25 . C24 . H241 . 111.3 no
C25 . C24 . H242 . 110.8 no
H241 . C24 . H242 . 109.1 no
C25 . C24 . H243 . 111.3 no
H241 . C24 . H243 . 108.6 no
H242 . C24 . H243 . 105.6 no
C24 . C25 . P1 . 116.0(2) yes
C24 . C25 . C26 . 111.7(3) yes
P1 . C25 . C26 . 110.9(2) yes
C24 . C25 . H251 . 106.8 no
P1 . C25 . H251 . 104.0 no
C26 . C25 . H251 . 106.8 no
C25 . C26 . H263 . 110.2 no
C25 . C26 . H262 . 109.5 no
H263 . C26 . H262 . 109.4 no
C25 . C26 . H261 . 111.7 no
H263 . C26 . H261 . 109.0 no
H262 . C26 . H261 . 107.0 no
P2 . B1 . N1 . 97.62(19) yes
P2 . B1 . F2 . 107.8(2) yes
N1 . B1 . F2 . 114.5(3) yes
P2 . B1 . F1 . 114.3(2) yes
N1 . B1 . F1 . 112.2(3) yes
F2 . B1 . F1 . 109.8(3) yes
_iucr_refine_instruction_details_constraints
;
#
# Punched on 17/01/11 at 17:16:05
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 1,X'S) H ( 13,X'S) H ( 12,X'S) H ( 11,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 6,X'S) H ( 61,X'S)
RIDE C ( 7,X'S) H ( 71,X'S)
RIDE C ( 8,X'S) H ( 83,X'S) H ( 82,X'S) H ( 81,X'S)
RIDE C ( 9,X'S) H ( 91,X'S)
RIDE C ( 10,X'S) H ( 103,X'S) H ( 102,X'S) H ( 101,X'S)
RIDE C ( 11,X'S) H ( 111,X'S) H ( 112,X'S) H ( 113,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 13,X'S) H ( 133,X'S) H ( 132,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 143,X'S) H ( 142,X'S) H ( 141,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 213,X'S) H ( 212,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 221,X'S)
RIDE C ( 23,X'S) H ( 233,X'S) H ( 232,X'S) H ( 231,X'S)
RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) H ( 243,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 26,X'S) H ( 263,X'S) H ( 262,X'S) H ( 261,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 17/01/11 at 17:16:05
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;