#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024811.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024811
loop_
_publ_author_name
'Christopher W. Bond'
'Alexander J. Cresswell'
'Stephen G. Davies'
'Ai M. Fletcher'
'Wataru Kurosawa'
'James A. Lee'
'Paul M. Roberts'
'Angela J. Russell'
'Andrew D. Smith'
'James E. Thomson'
_publ_contact_author_address
;Department of Chemistry
Chemistry Research laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6735
_journal_page_last               6748
_journal_paper_doi               10.1021/jo9012783
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C21 H26 B1 F4 N1 O3'
_chemical_formula_sum            'C21 H26 B F4 N O3'
_chemical_formula_weight         427.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-06-24
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                106.3042(9)
_cell_angle_beta                 91.0410(8)
_cell_angle_gamma                95.2761(9)
_cell_formula_units_Z            2
_cell_length_a                   8.8068(2)
_cell_length_b                   10.2538(2)
_cell_length_c                   11.8459(2)
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1021.27(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7652
_diffrn_reflns_theta_full        26.631
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         5.194
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.3059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000444
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 13.0 13.2 4.39 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0540
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0506
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3790
_reflns_number_total             4629
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.27
_oxford_diffrn_Wilson_scale      0.56
_oxford_refine_ls_r_factor_ref   0.0391
_oxford_refine_ls_scale          1.361(3)
_oxford_reflns_number_all        4629
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '6241406 SGD112'
_cod_data_source_file            jo9012783_si_006.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C21 H26 B1 F4 N1 O3'
_cod_database_code               4024811
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
F1 F 0.63874(11) -0.05895(10) -0.25163(10) 0.0401 1.0000 Uani . . . . . . .
B2 B 0.7476(2) -0.15013(19) -0.25340(16) 0.0243 1.0000 Uani . . . . . . .
F3 F 0.79612(14) -0.13619(12) -0.13799(9) 0.0514 1.0000 Uani . . . . . . .
F4 F 0.68359(12) -0.28245(10) -0.30568(10) 0.0419 1.0000 Uani . . . . . . .
F5 F 0.87004(12) -0.11980(12) -0.31504(10) 0.0503 1.0000 Uani . . . . . . .
O6 O 0.67093(12) 0.02357(11) 0.06449(9) 0.0292 1.0000 Uani . . . . . . .
C7 C 0.80001(17) 0.12143(15) 0.10711(13) 0.0196 1.0000 Uani . . . . . . .
C8 C 0.77359(16) 0.19419(14) 0.23745(12) 0.0174 1.0000 Uani . . . . . . .
N9 N 0.68892(13) 0.09516(12) 0.29370(10) 0.0160 1.0000 Uani . . . . . . .
C10 C 0.63173(16) 0.15884(15) 0.41547(12) 0.0192 1.0000 Uani . . . . . . .
C11 C 0.75354(16) 0.22575(15) 0.51003(12) 0.0198 1.0000 Uani . . . . . . .
C12 C 0.79731(18) 0.15606(16) 0.58860(13) 0.0251 1.0000 Uani . . . . . . .
C13 C 0.90067(19) 0.21929(18) 0.68214(14) 0.0321 1.0000 Uani . . . . . . .
C14 C 0.96027(19) 0.35258(19) 0.69814(15) 0.0343 1.0000 Uani . . . . . . .
C15 C 0.9168(2) 0.42387(18) 0.62175(15) 0.0333 1.0000 Uani . . . . . . .
C16 C 0.81374(19) 0.36066(16) 0.52788(14) 0.0264 1.0000 Uani . . . . . . .
C17 C 0.78131(16) -0.02264(14) 0.29443(13) 0.0182 1.0000 Uani . . . . . . .
C18 C 0.68108(17) -0.14680(15) 0.30216(13) 0.0203 1.0000 Uani . . . . . . .
C19 C 0.70596(19) -0.20674(16) 0.39171(14) 0.0257 1.0000 Uani . . . . . . .
C20 C 0.6188(2) -0.32699(16) 0.39301(16) 0.0326 1.0000 Uani . . . . . . .
C21 C 0.5064(2) -0.38649(17) 0.30595(17) 0.0347 1.0000 Uani . . . . . . .
C22 C 0.48094(19) -0.32664(17) 0.21746(16) 0.0336 1.0000 Uani . . . . . . .
C23 C 0.56840(18) -0.20827(16) 0.21453(15) 0.0274 1.0000 Uani . . . . . . .
C24 C 0.68426(18) 0.31640(16) 0.23536(13) 0.0240 1.0000 Uani . . . . . . .
C25 C 0.66692(18) 0.31376(18) 0.10570(14) 0.0290 1.0000 Uani . . . . . . .
C26 C 0.79473(17) 0.23456(16) 0.04703(13) 0.0230 1.0000 Uani . . . . . . .
O27 O 0.93463(12) 0.32714(10) 0.07898(9) 0.0242 1.0000 Uani . . . . . . .
C28 C 1.05517(18) 0.29134(16) 0.01155(14) 0.0231 1.0000 Uani . . . . . . .
O29 O 1.04917(13) 0.18984(12) -0.07010(9) 0.0311 1.0000 Uani . . . . . . .
C30 C 1.19023(19) 0.39490(17) 0.05141(16) 0.0337 1.0000 Uani . . . . . . .
H71 H 0.8977 0.0796 0.0969 0.0233 1.0000 Uiso R . . . . . .
H81 H 0.8732 0.2253 0.2817 0.0214 1.0000 Uiso R . . . . . .
H101 H 0.5735 0.0816 0.4352 0.0245 1.0000 Uiso R . . . . . .
H102 H 0.5621 0.2258 0.4073 0.0236 1.0000 Uiso R . . . . . .
H121 H 0.7543 0.0634 0.5780 0.0321 1.0000 Uiso R . . . . . .
H131 H 0.9298 0.1686 0.7358 0.0394 1.0000 Uiso R . . . . . .
H141 H 1.0333 0.3963 0.7633 0.0405 1.0000 Uiso R . . . . . .
H151 H 0.9561 0.5182 0.6324 0.0397 1.0000 Uiso R . . . . . .
H161 H 0.7819 0.4124 0.4747 0.0315 1.0000 Uiso R . . . . . .
H172 H 0.8565 0.0114 0.3624 0.0222 1.0000 Uiso R . . . . . .
H171 H 0.8330 -0.0444 0.2201 0.0233 1.0000 Uiso R . . . . . .
H191 H 0.7858 -0.1639 0.4537 0.0335 1.0000 Uiso R . . . . . .
H201 H 0.6385 -0.3671 0.4560 0.0428 1.0000 Uiso R . . . . . .
H211 H 0.4449 -0.4699 0.3063 0.0426 1.0000 Uiso R . . . . . .
H221 H 0.4016 -0.3699 0.1571 0.0416 1.0000 Uiso R . . . . . .
H231 H 0.5522 -0.1661 0.1521 0.0336 1.0000 Uiso R . . . . . .
H242 H 0.5843 0.3084 0.2696 0.0324 1.0000 Uiso R . . . . . .
H241 H 0.7435 0.4021 0.2795 0.0329 1.0000 Uiso R . . . . . .
H251 H 0.6743 0.4081 0.0961 0.0393 1.0000 Uiso R . . . . . .
H252 H 0.5679 0.2613 0.0700 0.0398 1.0000 Uiso R . . . . . .
H261 H 0.7810 0.1981 -0.0400 0.0281 1.0000 Uiso R . . . . . .
H301 H 1.2754 0.3684 0.0009 0.0538 1.0000 Uiso R . . . . . .
H303 H 1.1625 0.4836 0.0489 0.0541 1.0000 Uiso R . . . . . .
H302 H 1.2197 0.3998 0.1332 0.0539 1.0000 Uiso R . . . . . .
H91 H 0.6028 0.0573 0.2439 0.0261 1.0000 Uiso R . . . . . .
H61 H 0.6893 -0.0247 -0.0038 0.0448 1.0000 Uiso R . . . . . .
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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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 . B2 . F3 . 108.25(14) yes
F1 . B2 . F4 . 109.70(13) yes
F3 . B2 . F4 . 109.95(15) yes
F1 . B2 . F5 . 109.72(14) yes
F3 . B2 . F5 . 109.32(14) yes
F4 . B2 . F5 . 109.87(14) yes
C7 . O6 . H61 . 107.8 no
O6 . C7 . C8 . 106.75(11) yes
O6 . C7 . C26 . 108.36(12) yes
C8 . C7 . C26 . 103.48(11) yes
O6 . C7 . H71 . 112.5 no
C8 . C7 . H71 . 112.6 no
C26 . C7 . H71 . 112.6 no
C7 . C8 . N9 . 109.95(11) yes
C7 . C8 . C24 . 105.64(12) yes
N9 . C8 . C24 . 113.23(11) yes
C7 . C8 . H81 . 109.8 no
N9 . C8 . H81 . 107.0 no
C24 . C8 . H81 . 111.2 no
C8 . N9 . C10 . 115.34(11) yes
C8 . N9 . C17 . 111.36(10) yes
C10 . N9 . C17 . 110.88(11) yes
C8 . N9 . H91 . 105.4 no
C10 . N9 . H91 . 106.9 no
C17 . N9 . H91 . 106.3 no
N9 . C10 . C11 . 115.59(11) yes
N9 . C10 . H101 . 104.1 no
C11 . C10 . H101 . 110.1 no
N9 . C10 . H102 . 107.1 no
C11 . C10 . H102 . 110.0 no
H101 . C10 . H102 . 109.7 no
C10 . C11 . C12 . 119.50(14) yes
C10 . C11 . C16 . 121.49(14) yes
C12 . C11 . C16 . 118.74(14) yes
C11 . C12 . C13 . 120.66(15) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 119.94(16) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 120.8 no
C13 . C14 . C15 . 120.20(16) yes
C13 . C14 . H141 . 119.7 no
C15 . C14 . H141 . 120.1 no
C14 . C15 . C16 . 119.96(16) yes
C14 . C15 . H151 . 121.4 no
C16 . C15 . H151 . 118.7 no
C11 . C16 . C15 . 120.50(16) yes
C11 . C16 . H161 . 119.9 no
C15 . C16 . H161 . 119.6 no
N9 . C17 . C18 . 111.82(11) yes
N9 . C17 . H172 . 106.6 no
C18 . C17 . H172 . 111.9 no
N9 . C17 . H171 . 106.2 no
C18 . C17 . H171 . 109.3 no
H172 . C17 . H171 . 110.8 no
C17 . C18 . C19 . 120.82(14) yes
C17 . C18 . C23 . 119.91(14) yes
C19 . C18 . C23 . 119.13(15) yes
C18 . C19 . C20 . 120.06(16) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 120.5 no
C19 . C20 . C21 . 120.25(16) yes
C19 . C20 . H201 . 118.6 no
C21 . C20 . H201 . 121.2 no
C20 . C21 . C22 . 119.73(16) yes
C20 . C21 . H211 . 120.8 no
C22 . C21 . H211 . 119.4 no
C21 . C22 . C23 . 120.41(17) yes
C21 . C22 . H221 . 118.6 no
C23 . C22 . H221 . 121.0 no
C18 . C23 . C22 . 120.40(16) yes
C18 . C23 . H231 . 118.6 no
C22 . C23 . H231 . 121.0 no
C8 . C24 . C25 . 106.13(12) yes
C8 . C24 . H242 . 110.7 no
C25 . C24 . H242 . 111.2 no
C8 . C24 . H241 . 109.7 no
C25 . C24 . H241 . 109.2 no
H242 . C24 . H241 . 109.8 no
C24 . C25 . C26 . 104.56(12) yes
C24 . C25 . H251 . 111.8 no
C26 . C25 . H251 . 111.8 no
C24 . C25 . H252 . 110.1 no
C26 . C25 . H252 . 107.8 no
H251 . C25 . H252 . 110.6 no
C7 . C26 . C25 . 103.67(12) yes
C7 . C26 . O27 . 109.14(12) yes
C25 . C26 . O27 . 106.47(13) yes
C7 . C26 . H261 . 112.3 no
C25 . C26 . H261 . 114.5 no
O27 . C26 . H261 . 110.3 no
C26 . O27 . C28 . 116.05(12) yes
O27 . C28 . O29 . 122.82(14) yes
O27 . C28 . C30 . 111.05(14) yes
O29 . C28 . C30 . 126.12(15) yes
C28 . C30 . H301 . 109.9 no
C28 . C30 . H303 . 109.2 no
H301 . C30 . H303 . 110.5 no
C28 . C30 . H302 . 108.6 no
H301 . C30 . H302 . 109.7 no
H303 . C30 . H302 . 108.9 no
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
F1 . B2 . 1.396(2) yes
B2 . F3 . 1.389(2) yes
B2 . F4 . 1.385(2) yes
B2 . F5 . 1.373(2) yes
O6 . C7 . 1.4280(17) yes
O6 . H61 . 0.849 no
C7 . C8 . 1.5469(19) yes
C7 . C26 . 1.525(2) yes
C7 . H71 . 0.991 no
C8 . N9 . 1.5132(17) yes
C8 . C24 . 1.5453(19) yes
C8 . H81 . 0.992 no
N9 . C10 . 1.5227(17) yes
N9 . C17 . 1.5191(17) yes
N9 . H91 . 0.936 no
C10 . C11 . 1.505(2) yes
C10 . H101 . 0.989 no
C10 . H102 . 0.985 no
C11 . C12 . 1.392(2) yes
C11 . C16 . 1.392(2) yes
C12 . C13 . 1.389(2) yes
C12 . H121 . 0.963 no
C13 . C14 . 1.378(2) yes
C13 . H131 . 0.971 no
C14 . C15 . 1.382(2) yes
C14 . H141 . 0.972 no
C15 . C16 . 1.390(2) yes
C15 . H151 . 0.969 no
C16 . H161 . 0.983 no
C17 . C18 . 1.5068(19) yes
C17 . H172 . 0.994 no
C17 . H171 . 0.978 no
C18 . C19 . 1.390(2) yes
C18 . C23 . 1.393(2) yes
C19 . C20 . 1.395(2) yes
C19 . H191 . 0.985 no
C20 . C21 . 1.384(3) yes
C20 . H201 . 0.968 no
C21 . C22 . 1.380(3) yes
C21 . H211 . 0.971 no
C22 . C23 . 1.386(2) yes
C22 . H221 . 0.971 no
C23 . H231 . 0.971 no
C24 . C25 . 1.533(2) yes
C24 . H242 . 0.983 no
C24 . H241 . 0.983 no
C25 . C26 . 1.513(2) yes
C25 . H251 . 1.002 no
C25 . H252 . 1.001 no
C26 . O27 . 1.4589(18) yes
C26 . H261 . 0.994 no
O27 . C28 . 1.3556(17) yes
C28 . O29 . 1.2018(18) yes
C28 . C30 . 1.494(2) yes
C30 . H301 . 0.978 no
C30 . H303 . 0.971 no
C30 . H302 . 0.985 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O29 1_556 144 0.97 2.46 3.293(2) yes
C17 . H171 . O29 2_755 153 0.98 2.31 3.207(2) yes
C23 . H231 . O6 . 142 0.97 2.60 3.415(2) yes
