data_global 
_audit_creation_date        09-12-10
_audit_creation_method CRYSTALS_ver_12.87

_oxford_structure_analysis_title  'caacbf3'
_chemical_name_systematic         ?
_chemical_melting_point           ?

#looking for refcif 
 
 
# Check this file using the IUCr facility at: 
# http://checkcif.iucr.org/ 
 
# The content below is held in the file 'script/refcif.dat'. This is a text 
# file which you may edit to reflect local conditions. 
# Items which need looking at are represented by a '?'. 
# Items for which there are choices are prefixed with 'choose from'. 
 
_publ_contact_letter 
; 
 Please consider this CIF submission for 
 publication as a Short Format Paper in Acta 
 Crystallographica E. 
; 
_publ_contact_author_name         'E. Lacôte' 
_publ_contact_author_address 
; 
Université Pierre et Marie Curie - Paris 6
Laboratoire de chimie organique - CNRS UMR 7611
Institut de Chimie Moléculaire (FR2769)
Case 229 - 4 place Jussieu 
75005 Paris 
France
; 
 
_publ_contact_author_phone        '00 33 1 44 27 25 47'
_publ_contact_author_fax          '00 33 1 44 27 73 60' 
_publ_contact_author_email        'emmanuel.lacote@upmc.fr' 
_publ_requested_journal           'Organic Letter'
_publ_requested_category          EO # choose from: FI FM FO CI CM CO AD 
_publ_requested_coeditor_name     'Prof William Clegg' 
 
_publ_section_title 
# Title of paper - generally just the systematic or trivial name 
; 
Estimated rate constants for radical hydrogen abstraction from
N-heterocyclic carbene-borane complexes 
; 
 
# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary. 
loop_ 
 _publ_author_name 
 _publ_author_address 
       'Andrey Solovyev'
; Department of Chemistry
University of Pittsburgh
Pittsburgh
PA 15260 USA
;
      'Shau-Hua Ueng'
; Department of Chemistry
University of Pittsburgh
Pittsburgh
PA 15260 USA
;
      'Julien Monot'
; Université Pierre et Marie Curie - Paris 6
Laboratoire de chimie organique - CNRS UMR 7611
Institut de Chimie Moléculaire (FR2769)
Case 229 - 4 place Jussieu 
75005 Paris 
France
;
      'Louis Fensterbank'
; Université Pierre et Marie Curie - Paris 6
Laboratoire de chimie organique - CNRS UMR 7611
Institut de Chimie Moléculaire (FR2769)
Case 229 - 4 place Jussieu 
75005 Paris 
France
;
      'Max Malacria'
; Université Pierre et Marie Curie - Paris 6
Laboratoire de chimie organique - CNRS UMR 7611
Institut de Chimie Moléculaire (FR2769)
Case 229 - 4 place Jussieu 
75005 Paris 
France
;
      'Emmanuel Lacôte'
; Université Pierre et Marie Curie - Paris 6
Laboratoire de chimie organique - CNRS UMR 7611
Institut de Chimie Moléculaire (FR2769)
Case 229 - 4 place Jussieu 
75005 Paris 
France
;
      'Dennis P. Curran*'
; Department of Chemistry
University of Pittsburgh
Pittsburgh
PA 15260 USA
;
 
 
_publ_section_abstract 
# Text of the abstract 
# (a) The Abstract must be self-contained and comprehensible 
# without the rest of the paper. This means no references 
# to atom names or to compound numbers; compounds must be 
# identified as the title compound, or by name or by some other 
# means such as derivatives of each other (e.g. "the 
# corresponding ketone"). 
# (b) The chemical formula of "the title compound" must be given. 
# (c) Any crystallographic molecular symmetry should be 
# mentioned, and also the presence of more than one molecule 
# in the asymmetric unit (i.e. anything other than Z'=1). 
; 
? 
; 
 
_publ_section_related_literature  # Not in version 2.3.1 
############################################################### 
# Essential references (e.g. to the origin of the material studied, related 
# structural studies, and to information supporting the reported structure) 
# should be cited in this section, with appropriate very brief explanatory 
# text, for example `The synthesis of the complex is described by Jones 
# (2001). The anhydrous complex has essentially the same coordination 
# geometry (Smith, 2003).' In addition, all references included in the 
# supplementary materials, but not elsewhere in the published article, 
# should be given here. The simple text `For related literature, see:...' 
# may be used, but further details should be provided in the Comment 
# section, which forms part of the supplementary material. 
############################################################### 
; 
? 
; 
 
_publ_section_comment 
# Text of the paper 
# Note that atoms are referenced as N2, not N(2) or N~2~ 
# If text containing () occur within (), the outer ones should be [] 
# Figures should be referenced as Fig. 
; 
? 
; 
_publ_section_acknowledgements    # Acknowledgments 
; 
? 
; 
_publ_section_figure_captions 
# Captions to figures - Start each caption on a new line after a blank line 
; 
Fig. 1. 
The title compound with displacement ellipsoids drawn at the 50% 
probability level. H atoms are shown as spheres of 
arbitary radius. 
 
; 
 
 
_publ_section_exptl_refinement 
# Some potentially useful phrases are donated by Bill Clegg: 
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 
 
The absolute configuration was arbitrarily assigned. 
 
The relatively large ratio of minimum to maximum corrections applied 
in the multiscan process (1:nnn) reflect changes in the illuminated 
volume of the crystal. 
 
Changes in illuminated volume were kept to a minimum, and were 
taken into account (Görbitz, 1999) by the multi-scan inter-frame 
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). 
 
 
Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. 
 
 
 
 
The H atoms were all located in a difference map, but those 
attached to carbon atoms were repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98, 
N---H in the range 0.86--0.89 
N---H to 0.86 
O---H = 0.82 
Å) 
and 
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom), 
after which the positions were refined with riding constraints. 
 
; 
 
_publ_section_exptl_prep 
# Brief details or a reference. Include solvent if known 
; 
? 
; 
 
# Hand-made tables can be put in the cif. The number of columns 
# is set in the loop header. 
# The contants of each column can either be a piece of text 
# without any spaces (eg a number) or other text enclosed in " " 
# Remove the leading # in the following example 
 
#geom_extra_table_head_A 
#; 
#Table 2. 
#Molecular parameters deviating most from MOGUL averages 
#; 
# 
#loop_ 
#_geom_extra_tableA_col_1 
#_geom_extra_tableA_col_2 
#_geom_extra_tableA_col_3 
#_geom_extra_tableA_col_4 
# 
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" 
#N5-C6-C4 129 124 "7 (\%)" 
#C3-O10-C2 105 109 "2 (\%)" 
#C6-O7 1.25 1.22 ".02 (\%A)" 
# 
 
data_1 
 
_exptl_special_details 
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. 
; 
_refine_special_details 
; 
? 
; 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                    8.3106(11)
_cell_length_b                    16.120(2)
_cell_length_c                    16.9678(18)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2273.2(5)
 
_symmetry_cell_setting            'Orthorhombic' 
_symmetry_space_group_name_H-M    'P b c 21 ' 
_symmetry_space_group_name_Hall   'P 2c -2b'
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,y+1/2,z'
 'x,-y+1/2,z+1/2'
 '-x,-y,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'
 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'
 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'
 
 
_cell_formula_units_Z                    4

# Given Formula = C25 H33 B1 F3 N1 
# Dc =      1.21 Fooo =    888.00 Mu =      0.86 M =    415.35
# Found Formula = C25 H33 B1 F3 N1 
# Dc =      1.21 FOOO =    888.00 Mu =      0.86 M =    415.35

_chemical_formula_sum             'C25 H33 B1 F3 N1'
_chemical_formula_moiety          'C25 H33 B1 F3 N1'
_chemical_compound_source                ?
_chemical_formula_weight            415.35
 
 
_cell_measurement_reflns_used          135
_cell_measurement_theta_min              5
_cell_measurement_theta_max             22
_cell_measurement_temperature          200
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_min           0.190 
_exptl_crystal_size_mid           0.250 
_exptl_crystal_size_max           0.290 
 
_exptl_crystal_density_diffrn     1.214 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              888 
_exptl_absorpt_coefficient_mu     0.086 
 
# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_process_details    'SADABS (Siemens, 1996)' 
_exptl_absorpt_correction_T_min   0.97 
_exptl_absorpt_correction_T_max   0.98 
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device        'Nonius KappaCCD' 
_diffrn_measurement_device_type   'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method        'φ & ω scans' 
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'COLLECT (Nonius, 2001).' 
_computing_cell_refinement      'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' 
_computing_data_reduction         'EvalCCD (Duisenberg & Schreurs 1990-2000)'  
_computing_structure_solution     'Superflip (Palatinus & Chapuis, 2007)'
_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        200
_diffrn_reflns_number             11847 
_reflns_number_total              3695 
_diffrn_reflns_av_R_equivalents   0.042 
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3695 
# Theoretical number of reflections is about 6625 
 
 
_diffrn_reflns_theta_min          1.742 
_diffrn_reflns_theta_max          29.991 
_diffrn_measured_fraction_theta_max 0.986 
 
_diffrn_reflns_theta_full         25.493 
_diffrn_measured_fraction_theta_full 0.994 
 
 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -22 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -23 
_diffrn_reflns_limit_l_max        15 
_reflns_limit_h_min               0 
_reflns_limit_h_max               11 
_reflns_limit_k_min               0 
_reflns_limit_k_max               22 
_reflns_limit_l_min               0 
_reflns_limit_l_max               23 
 

 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    geom
 
_refine_diff_density_min          -0.34 
_refine_diff_density_max          0.38 
 
 
# 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>-3.0\s(I)
_refine_ls_number_reflns          3692 
_refine_ls_number_restraints      1 
_refine_ls_number_parameters      272 
_oxford_refine_ls_R_factor_ref    0.0866 
_refine_ls_wR_factor_ref          0.1157 
_refine_ls_goodness_of_fit_ref    0.9218 
_refine_ls_shift/su_max           0.0054975 
_refine_ls_shift/su_mean          0.4437670 
 
 
# The values computed from all data 
_oxford_reflns_number_all         3694 
_refine_ls_R_factor_all           0.0867 
_refine_ls_wR_factor_all          0.1161 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0σ(I)
_reflns_number_gt                 2509 
_refine_ls_R_factor_gt            0.0466 
_refine_ls_wR_factor_gt           0.1007 
 
# 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  'unk' 
 
 
_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/[σ²(F²) + ( 0.06P)² + 0.53P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references 
; 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. 
 
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, 
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. 
New York: Academic Press. 
 
Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. 
 
Siemens Industrial Automation, Inc (1996). 
SADABS: Area-Detector Absorption Correction;: 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.1027(2) 0.31937(13) 0.47879(14) 0.0246 1.0000 Uani . . . . . . . 
C2 C -0.0674(3) 0.28741(13) 0.49276(14) 0.0258 1.0000 Uani . . . . . . . 
C3 C -0.1671(2) 0.35226(14) 0.44774(14) 0.0272 1.0000 Uani . . . . . . . 
C4 C -0.0736(2) 0.43257(13) 0.45320(14) 0.0236 1.0000 Uani . . . . . . . 
C5 C -0.1068(3) 0.28668(14) 0.58167(14) 0.0292 1.0000 Uani . . . . . . . 
C6 C -0.2675(3) 0.28082(16) 0.60384(17) 0.0375 1.0000 Uani . . . . . . . 
C7 C -0.3098(4) 0.28039(19) 0.68243(18) 0.0475 1.0000 Uani . . . . . . . 
C8 C -0.1942(4) 0.2867(2) 0.74027(17) 0.0557 1.0000 Uani . . . . . . . 
C9 C -0.0353(4) 0.2905(2) 0.71934(17) 0.0498 1.0000 Uani . . . . . . . 
C10 C 0.0081(3) 0.29027(16) 0.63998(16) 0.0377 1.0000 Uani . . . . . . . 
C11 C -0.0919(3) 0.20016(15) 0.45970(18) 0.0407 1.0000 Uani . . . . . . . 
C12 C -0.0914(3) 0.48573(16) 0.38011(16) 0.0339 1.0000 Uani . . . . . . . 
C13 C -0.1146(3) 0.48332(15) 0.52620(15) 0.0306 1.0000 Uani . . . . . . . 
C14 C 0.2359(2) 0.45035(14) 0.44575(15) 0.0271 1.0000 Uani . . . . . . . 
C15 C 0.3027(3) 0.49315(14) 0.50955(16) 0.0306 1.0000 Uani . . . . . . . 
C16 C 0.4247(3) 0.54949(16) 0.49297(19) 0.0404 1.0000 Uani . . . . . . . 
C17 C 0.4776(3) 0.56216(18) 0.4177(2) 0.0475 1.0000 Uani . . . . . . . 
C18 C 0.4147(3) 0.51710(19) 0.35638(19) 0.0455 1.0000 Uani . . . . . . . 
C19 C 0.2932(3) 0.45929(16) 0.36842(16) 0.0331 1.0000 Uani . . . . . . . 
C20 C 0.2411(3) 0.40585(19) 0.29938(17) 0.0407 1.0000 Uani . . . . . . . 
C21 C 0.1915(4) 0.4568(2) 0.22734(18) 0.0581 1.0000 Uani . . . . . . . 
C22 C 0.3758(4) 0.3466(2) 0.2756(2) 0.0565 1.0000 Uani . . . . . . . 
C23 C 0.2579(3) 0.47614(16) 0.59481(16) 0.0348 1.0000 Uani . . . . . . . 
C24 C 0.3869(4) 0.4222(2) 0.63375(19) 0.0528 1.0000 Uani . . . . . . . 
C25 C 0.2325(4) 0.55505(19) 0.64289(19) 0.0502 1.0000 Uani . . . . . . . 
N1 N 0.09754(19) 0.39703(10) 0.45972(11) 0.0218 1.0000 Uani . . . . . . . 
F1 F 0.2465(2) 0.21544(10) 0.40421(12) 0.0522 1.0000 Uani . . . . . . . 
F2 F 0.40633(16) 0.30163(10) 0.47499(12) 0.0496 1.0000 Uani . . . . . . . 
F3 F 0.2612(2) 0.20261(11) 0.53754(13) 0.0603 1.0000 Uani . . . . . . . 
B1 B 0.2647(3) 0.25781(19) 0.4754(2) 0.0388 1.0000 Uani . . . . . . . 
H31 H -0.2701 0.3585 0.4711 0.0486(14) 1.0000 Uiso . . . . . . . 
H32 H -0.1795 0.3362 0.3940 0.0486(14) 1.0000 Uiso . . . . . . . 
H61 H -0.3487 0.2769 0.5643 0.0486(14) 1.0000 Uiso . . . . . . . 
H71 H -0.4198 0.2759 0.6967 0.0486(14) 1.0000 Uiso . . . . . . . 
H81 H -0.2245 0.2883 0.7939 0.0486(14) 1.0000 Uiso . . . . . . . 
H91 H 0.0452 0.2930 0.7588 0.0486(14) 1.0000 Uiso . . . . . . . 
H101 H 0.1187 0.2928 0.6258 0.0486(14) 1.0000 Uiso . . . . . . . 
H111 H -0.1993 0.1827 0.4694 0.0486(14) 1.0000 Uiso . . . . . . . 
H112 H -0.0191 0.1630 0.4842 0.0486(14) 1.0000 Uiso . . . . . . . 
H113 H -0.0731 0.2006 0.4043 0.0486(14) 1.0000 Uiso . . . . . . . 
H121 H -0.0305 0.5352 0.3861 0.0486(14) 1.0000 Uiso . . . . . . . 
H122 H -0.2014 0.4993 0.3724 0.0486(14) 1.0000 Uiso . . . . . . . 
H123 H -0.0528 0.4560 0.3354 0.0486(14) 1.0000 Uiso . . . . . . . 
H131 H -0.0525 0.5328 0.5262 0.0486(14) 1.0000 Uiso . . . . . . . 
H132 H -0.0912 0.4518 0.5718 0.0486(14) 1.0000 Uiso . . . . . . . 
H133 H -0.2258 0.4970 0.5253 0.0486(14) 1.0000 Uiso . . . . . . . 
H161 H 0.4727 0.5798 0.5347 0.0486(14) 1.0000 Uiso . . . . . . . 
H171 H 0.5583 0.6026 0.4073 0.0486(14) 1.0000 Uiso . . . . . . . 
H181 H 0.4552 0.5256 0.3044 0.0486(14) 1.0000 Uiso . . . . . . . 
H201 H 0.1512 0.3736 0.3153 0.0486(14) 1.0000 Uiso . . . . . . . 
H211 H 0.1601 0.4205 0.1858 0.0486(14) 1.0000 Uiso . . . . . . . 
H212 H 0.2798 0.4897 0.2103 0.0486(14) 1.0000 Uiso . . . . . . . 
H213 H 0.1038 0.4918 0.2407 0.0486(14) 1.0000 Uiso . . . . . . . 
H221 H 0.3416 0.3137 0.2323 0.0486(14) 1.0000 Uiso . . . . . . . 
H222 H 0.4681 0.3778 0.2606 0.0486(14) 1.0000 Uiso . . . . . . . 
H223 H 0.4019 0.3119 0.3188 0.0486(14) 1.0000 Uiso . . . . . . . 
H231 H 0.1598 0.4460 0.5948 0.0486(14) 1.0000 Uiso . . . . . . . 
H241 H 0.3579 0.4118 0.6867 0.0486(14) 1.0000 Uiso . . . . . . . 
H242 H 0.4874 0.4501 0.6318 0.0486(14) 1.0000 Uiso . . . . . . . 
H243 H 0.3951 0.3710 0.6059 0.0486(14) 1.0000 Uiso . . . . . . . 
H251 H 0.2053 0.5404 0.6953 0.0486(14) 1.0000 Uiso . . . . . . . 
H252 H 0.3294 0.5865 0.6428 0.0486(14) 1.0000 Uiso . . . . . . . 
H253 H 0.1486 0.5866 0.6200 0.0486(14) 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
C1 0.0271(10) 0.0255(10) 0.0211(9) -0.0018(8) -0.0028(8) -0.0001(8) 
C2 0.0264(10) 0.0244(11) 0.0265(10) 0.0031(9) -0.0021(8) -0.0029(8) 
C3 0.0240(10) 0.0310(11) 0.0267(10) 0.0046(10) -0.0037(9) -0.0037(8) 
C4 0.0173(8) 0.0275(10) 0.0259(10) 0.0030(9) -0.0009(8) 0.0031(7) 
C5 0.0352(12) 0.0261(12) 0.0264(11) 0.0073(9) 0.0004(10) -0.0003(9) 
C6 0.0348(12) 0.0394(14) 0.0383(13) 0.0132(11) 0.0010(11) -0.0010(10) 
C7 0.0413(14) 0.0572(19) 0.0440(16) 0.0200(14) 0.0100(13) 0.0058(13) 
C8 0.067(2) 0.071(2) 0.0299(14) 0.0192(14) 0.0098(14) 0.0181(16) 
C9 0.0557(17) 0.063(2) 0.0303(13) 0.0129(13) -0.0062(13) 0.0098(15) 
C10 0.0348(12) 0.0448(15) 0.0336(12) 0.0079(11) -0.0028(11) 0.0005(11) 
C11 0.0514(14) 0.0280(12) 0.0427(15) -0.0034(11) -0.0022(12) -0.0093(11) 
C12 0.0278(11) 0.0384(14) 0.0355(12) 0.0130(11) 0.0009(10) 0.0064(10) 
C13 0.0274(11) 0.0301(12) 0.0345(12) -0.0010(10) 0.0000(9) 0.0054(9) 
C14 0.0201(9) 0.0259(11) 0.0352(11) 0.0040(9) 0.0012(9) 0.0001(8) 
C15 0.0210(9) 0.0285(12) 0.0424(13) -0.0007(10) -0.0073(9) 0.0025(9) 
C16 0.0241(11) 0.0309(12) 0.0662(18) -0.0063(12) -0.0075(12) -0.0033(9) 
C17 0.0261(12) 0.0377(15) 0.079(2) 0.0027(14) 0.0076(13) -0.0090(11) 
C18 0.0311(12) 0.0482(16) 0.0572(17) 0.0121(14) 0.0130(12) -0.0049(12) 
C19 0.0224(10) 0.0359(13) 0.0410(13) 0.0059(11) 0.0032(10) 0.0006(9) 
C20 0.0349(13) 0.0574(17) 0.0300(12) 0.0005(12) 0.0092(10) -0.0030(12) 
C21 0.0503(17) 0.087(3) 0.0369(15) 0.0089(16) 0.0063(14) -0.0074(17) 
C22 0.0541(17) 0.067(2) 0.0483(16) -0.0130(16) 0.0173(14) 0.0033(16) 
C23 0.0320(12) 0.0365(13) 0.0358(12) -0.0046(11) -0.0105(10) 0.0012(10) 
C24 0.0545(17) 0.0549(18) 0.0490(17) -0.0002(14) -0.0241(14) 0.0056(14) 
C25 0.0565(17) 0.0491(17) 0.0450(16) -0.0115(14) -0.0066(14) -0.0005(14) 
N1 0.0182(7) 0.0251(8) 0.0221(9) 0.0011(7) -0.0012(7) 0.0008(6) 
F1 0.0538(10) 0.0465(10) 0.0562(10) -0.0169(8) 0.0023(8) 0.0156(8) 
F2 0.0267(7) 0.0554(9) 0.0666(11) -0.0037(8) -0.0048(8) 0.0119(6) 
F3 0.0686(12) 0.0487(10) 0.0637(12) 0.0197(9) 0.0028(9) 0.0285(9) 
B1 0.0361(13) 0.0347(15) 0.0457(15) 0.0013(13) -0.0012(13) 0.0166(11) 

_refine_ls_extinction_method 
    'None'

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
C1 . C2 . 1.523(3)    yes
C1 . N1 . 1.294(3)    yes
C1 . B1 . 1.674(3)    yes
C2 . C3 . 1.537(3)    yes
C2 . C5 . 1.544(3)    yes
C2 . C11 . 1.528(3)    yes
C3 . C4 . 1.513(3)    yes
C3 . H31 . 0.948    no
C3 . H32 . 0.953    no
C4 . C12 . 1.515(3)    yes
C4 . C13 . 1.523(3)    yes
C4 . N1 . 1.538(2)    yes
C5 . C6 . 1.391(3)    yes
C5 . C10 . 1.376(3)    yes
C6 . C7 . 1.379(4)    yes
C6 . H61 . 0.954    no
C7 . C8 . 1.377(5)    yes
C7 . H71 . 0.949    no
C8 . C9 . 1.368(5)    yes
C8 . H81 . 0.945    no
C9 . C10 . 1.394(4)    yes
C9 . H91 . 0.947    no
C10 . H101 . 0.951    no
C11 . H111 . 0.950    no
C11 . H112 . 0.947    no
C11 . H113 . 0.954    no
C12 . H121 . 0.950    no
C12 . H122 . 0.949    no
C12 . H123 . 0.953    no
C13 . H131 . 0.950    no
C13 . H132 . 0.946    no
C13 . H133 . 0.950    no
C14 . C15 . 1.399(3)    yes
C14 . C19 . 1.403(3)    yes
C14 . N1 . 1.455(3)    yes
C15 . C16 . 1.390(3)    yes
C15 . C23 . 1.519(4)    yes
C16 . C17 . 1.367(4)    yes
C16 . H161 . 0.948    no
C17 . C18 . 1.372(5)    yes
C17 . H171 . 0.952    no
C18 . C19 . 1.390(4)    yes
C18 . H181 . 0.954    no
C19 . C20 . 1.517(4)    yes
C20 . C21 . 1.529(4)    yes
C20 . C22 . 1.526(4)    yes
C20 . H201 . 0.950    no
C21 . H211 . 0.953    no
C21 . H212 . 0.950    no
C21 . H213 . 0.949    no
C22 . H221 . 0.950    no
C22 . H222 . 0.953    no
C22 . H223 . 0.946    no
C23 . C24 . 1.530(4)    yes
C23 . C25 . 1.526(4)    yes
C23 . H231 . 0.949    no
C24 . H241 . 0.946    no
C24 . H242 . 0.950    no
C24 . H243 . 0.952    no
C25 . H251 . 0.947    no
C25 . H252 . 0.952    no
C25 . H253 . 0.946    no
F1 . B1 . 1.396(4)    yes
F2 . B1 . 1.372(3)    yes
F3 . B1 . 1.380(4)    yes
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
C2 . C1 . N1 . 109.62(17)    yes
C2 . C1 . B1 . 123.5(2)    yes
N1 . C1 . B1 . 126.26(19)    yes
C1 . C2 . C3 . 101.11(16)    yes
C1 . C2 . C5 . 110.56(18)    yes
C3 . C2 . C5 . 112.13(18)    yes
C1 . C2 . C11 . 112.20(19)    yes
C3 . C2 . C11 . 111.83(19)    yes
C5 . C2 . C11 . 108.89(19)    yes
C2 . C3 . C4 . 105.95(16)    yes
C2 . C3 . H31 . 110.6    no
C4 . C3 . H31 . 110.3    no
C2 . C3 . H32 . 110.4    no
C4 . C3 . H32 . 110.3    no
H31 . C3 . H32 . 109.3    no
C3 . C4 . C12 . 112.59(19)    yes
C3 . C4 . C13 . 113.24(18)    yes
C12 . C4 . C13 . 109.89(18)    yes
C3 . C4 . N1 . 99.25(16)    yes
C12 . C4 . N1 . 111.09(17)    yes
C13 . C4 . N1 . 110.39(17)    yes
C2 . C5 . C6 . 117.9(2)    yes
C2 . C5 . C10 . 123.7(2)    yes
C6 . C5 . C10 . 118.3(2)    yes
C5 . C6 . C7 . 120.4(2)    yes
C5 . C6 . H61 . 119.6    no
C7 . C6 . H61 . 120.0    no
C6 . C7 . C8 . 120.7(3)    yes
C6 . C7 . H71 . 119.5    no
C8 . C7 . H71 . 119.8    no
C7 . C8 . C9 . 119.4(3)    yes
C7 . C8 . H81 . 120.2    no
C9 . C8 . H81 . 120.4    no
C8 . C9 . C10 . 120.0(3)    yes
C8 . C9 . H91 . 120.0    no
C10 . C9 . H91 . 120.0    no
C9 . C10 . C5 . 121.0(2)    yes
C9 . C10 . H101 . 119.6    no
C5 . C10 . H101 . 119.4    no
C2 . C11 . H111 . 109.5    no
C2 . C11 . H112 . 109.6    no
H111 . C11 . H112 . 109.7    no
C2 . C11 . H113 . 109.5    no
H111 . C11 . H113 . 109.1    no
H112 . C11 . H113 . 109.4    no
C4 . C12 . H121 . 109.6    no
C4 . C12 . H122 . 109.7    no
H121 . C12 . H122 . 109.5    no
C4 . C12 . H123 . 109.6    no
H121 . C12 . H123 . 109.2    no
H122 . C12 . H123 . 109.3    no
C4 . C13 . H131 . 109.2    no
C4 . C13 . H132 . 109.3    no
H131 . C13 . H132 . 109.8    no
C4 . C13 . H133 . 109.2    no
H131 . C13 . H133 . 109.4    no
H132 . C13 . H133 . 109.8    no
C15 . C14 . C19 . 122.6(2)    yes
C15 . C14 . N1 . 118.6(2)    yes
C19 . C14 . N1 . 118.8(2)    yes
C14 . C15 . C16 . 117.1(2)    yes
C14 . C15 . C23 . 123.4(2)    yes
C16 . C15 . C23 . 119.3(2)    yes
C15 . C16 . C17 . 121.4(2)    yes
C15 . C16 . H161 . 119.5    no
C17 . C16 . H161 . 119.0    no
C16 . C17 . C18 . 120.5(2)    yes
C16 . C17 . H171 . 120.1    no
C18 . C17 . H171 . 119.4    no
C17 . C18 . C19 . 121.4(3)    yes
C17 . C18 . H181 . 119.4    no
C19 . C18 . H181 . 119.2    no
C14 . C19 . C18 . 116.9(2)    yes
C14 . C19 . C20 . 124.5(2)    yes
C18 . C19 . C20 . 118.3(2)    yes
C19 . C20 . C21 . 112.9(2)    yes
C19 . C20 . C22 . 110.5(2)    yes
C21 . C20 . C22 . 108.9(2)    yes
C19 . C20 . H201 . 108.4    no
C21 . C20 . H201 . 108.0    no
C22 . C20 . H201 . 108.0    no
C20 . C21 . H211 . 109.5    no
C20 . C21 . H212 . 109.6    no
H211 . C21 . H212 . 109.2    no
C20 . C21 . H213 . 109.6    no
H211 . C21 . H213 . 109.3    no
H212 . C21 . H213 . 109.5    no
C20 . C22 . H221 . 109.5    no
C20 . C22 . H222 . 109.3    no
H221 . C22 . H222 . 109.2    no
C20 . C22 . H223 . 109.5    no
H221 . C22 . H223 . 109.7    no
H222 . C22 . H223 . 109.5    no
C15 . C23 . C24 . 110.0(2)    yes
C15 . C23 . C25 . 113.1(2)    yes
C24 . C23 . C25 . 109.9(2)    yes
C15 . C23 . H231 . 107.6    no
C24 . C23 . H231 . 108.1    no
C25 . C23 . H231 . 107.9    no
C23 . C24 . H241 . 109.4    no
C23 . C24 . H242 . 109.3    no
H241 . C24 . H242 . 109.9    no
C23 . C24 . H243 . 109.2    no
H241 . C24 . H243 . 109.7    no
H242 . C24 . H243 . 109.3    no
C23 . C25 . H251 . 109.1    no
C23 . C25 . H252 . 109.0    no
H251 . C25 . H252 . 109.6    no
C23 . C25 . H253 . 109.4    no
H251 . C25 . H253 . 110.1    no
H252 . C25 . H253 . 109.7    no
C4 . N1 . C14 . 119.95(16)    yes
C4 . N1 . C1 . 114.14(16)    yes
C14 . N1 . C1 . 125.90(17)    yes
C1 . B1 . F1 . 103.5(2)    yes
C1 . B1 . F3 . 109.8(2)    yes
F1 . B1 . F3 . 110.1(2)    yes
C1 . B1 . F2 . 112.6(2)    yes
F1 . B1 . F2 . 109.9(2)    yes
F3 . B1 . F2 . 110.7(2)    yes
#end of refcif 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 

 
