#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:36:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179756 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/52/7005291.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_7005291
loop_
_publ_author_name
'Ugolotti, Juri'
'Hellstrom, Sondra'
'Britovsek, George J. P.'
'Jones, Tim S.'
'Hunt, Patricia'
'White, Andrew J. P.'
_publ_section_title
;
 Synthesis and characterisation of luminescent fluorinated organoboron
 compounds.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1425
_journal_page_last               1432
_journal_paper_doi               10.1039/b700317j
_journal_year                    2007
_chemical_formula_sum            'C21 H6 B F10 N O'
_chemical_formula_weight         489.08
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.164(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3409(13)
_cell_length_b                   7.8053(6)
_cell_length_c                   15.4746(14)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.9800
_cell_measurement_theta_min      2.8948
_cell_volume                     1842.2(3)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54248
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16343
_diffrn_reflns_theta_full        71.18
_diffrn_reflns_theta_max         71.18
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    1.605
_exptl_absorpt_correction_T_max  0.95253
_exptl_absorpt_correction_T_min  0.62708
_exptl_absorpt_correction_type   'numeric analytical'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00080(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                2555
_reflns_number_total             3484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700317j.txt
_cod_data_source_block           Compound_2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/c
_cod_database_code               7005291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
B B 0.26769(13) 0.6492(2) 0.39846(14) 0.0339(5) Uani 1 1 d . . .
N1 N 0.30568(9) 0.84515(17) 0.40733(9) 0.0327(3) Uani 1 1 d . . .
C2 C 0.27081(13) 0.9970(2) 0.42142(12) 0.0394(4) Uani 1 1 d . . .
H2A H 0.2115 1.0048 0.4334 0.047 Uiso 1 1 calc R . .
C3 C 0.32164(14) 1.1459(2) 0.41861(13) 0.0464(5) Uani 1 1 d . . .
H3A H 0.2963 1.2539 0.4293 0.056 Uiso 1 1 calc R . .
C4 C 0.40689(14) 1.1386(2) 0.40082(13) 0.0467(5) Uani 1 1 d . . .
H4A H 0.4400 1.2410 0.3986 0.056 Uiso 1 1 calc R . .
C5 C 0.44573(12) 0.9790(2) 0.38568(12) 0.0383(4) Uani 1 1 d . . .
C6 C 0.53136(13) 0.9435(3) 0.36476(14) 0.0474(5) Uani 1 1 d . . .
H6A H 0.5717 1.0344 0.3599 0.057 Uiso 1 1 calc R . .
C7 C 0.55592(13) 0.7777(3) 0.35154(14) 0.0495(5) Uani 1 1 d . . .
H7A H 0.6136 0.7568 0.3372 0.059 Uiso 1 1 calc R . .
C8 C 0.49944(12) 0.6361(2) 0.35824(13) 0.0430(5) Uani 1 1 d . . .
H8A H 0.5188 0.5226 0.3490 0.052 Uiso 1 1 calc R . .
C9 C 0.41653(11) 0.6668(2) 0.37837(12) 0.0349(4) Uani 1 1 d . . .
O9 O 0.35098(7) 0.55579(14) 0.38826(8) 0.0377(3) Uani 1 1 d . . .
C10 C 0.39108(11) 0.8369(2) 0.39075(11) 0.0322(4) Uani 1 1 d . . .
C11 C 0.23181(11) 0.5856(2) 0.48811(11) 0.0326(4) Uani 1 1 d . . .
C12 C 0.28368(11) 0.6083(2) 0.56661(12) 0.0356(4) Uani 1 1 d . . .
F12 F 0.36071(7) 0.69423(14) 0.56796(7) 0.0466(3) Uani 1 1 d . . .
C13 C 0.26381(12) 0.5452(2) 0.64516(12) 0.0393(4) Uani 1 1 d . . .
F13 F 0.31887(8) 0.57007(16) 0.71757(7) 0.0553(3) Uani 1 1 d . . .
C14 C 0.18712(13) 0.4548(2) 0.64851(13) 0.0428(5) Uani 1 1 d . . .
F14 F 0.16694(8) 0.39257(16) 0.72470(7) 0.0590(3) Uani 1 1 d . . .
C15 C 0.13262(11) 0.4287(2) 0.57355(13) 0.0405(4) Uani 1 1 d . . .
F15 F 0.05875(7) 0.33956(15) 0.57609(8) 0.0577(3) Uani 1 1 d . . .
C16 C 0.15600(11) 0.4922(2) 0.49554(12) 0.0361(4) Uani 1 1 d . . .
F16 F 0.10113(7) 0.45319(15) 0.42471(7) 0.0505(3) Uani 1 1 d . . .
C17 C 0.19916(11) 0.6400(2) 0.31056(12) 0.0337(4) Uani 1 1 d . . .
C18 C 0.11981(12) 0.7274(2) 0.30423(12) 0.0370(4) Uani 1 1 d . . .
F18 F 0.09862(6) 0.81763(14) 0.37401(7) 0.0459(3) Uani 1 1 d . . .
C19 C 0.05950(12) 0.7295(2) 0.23184(13) 0.0434(5) Uani 1 1 d . . .
F19 F -0.01546(8) 0.81752(16) 0.23162(9) 0.0627(4) Uani 1 1 d . . .
C20 C 0.07691(14) 0.6394(2) 0.15928(13) 0.0469(5) Uani 1 1 d . . .
F20 F 0.01966(9) 0.63948(17) 0.08756(8) 0.0707(4) Uani 1 1 d . . .
C21 C 0.15434(14) 0.5510(2) 0.16127(12) 0.0458(5) Uani 1 1 d . . .
F21 F 0.17327(9) 0.46344(16) 0.09071(8) 0.0661(4) Uani 1 1 d . . .
C22 C 0.21334(12) 0.5520(2) 0.23516(13) 0.0395(4) Uani 1 1 d . . .
F22 F 0.28687(7) 0.45961(16) 0.23069(8) 0.0578(3) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O9 B C11 108.26(14) . . ?
O9 B C17 111.90(15) . . ?
C11 B C17 116.89(15) . . ?
O9 B N1 99.43(13) . . ?
C11 B N1 111.35(14) . . ?
C17 B N1 107.64(14) . . ?
C2 N1 C10 119.04(15) . . ?
C2 N1 B 134.55(15) . . ?
C10 N1 B 106.28(13) . . ?
N1 C2 C3 119.95(17) . . ?
C4 C3 C2 121.27(17) . . ?
C3 C4 C5 120.04(17) . . ?
C10 C5 C4 115.14(17) . . ?
C10 C5 C6 115.78(16) . . ?
C4 C5 C6 129.07(18) . . ?
C7 C6 C5 119.78(17) . . ?
C6 C7 C8 123.16(18) . . ?
C9 C8 C7 118.20(17) . . ?
O9 C9 C8 129.65(16) . . ?
O9 C9 C10 111.76(15) . . ?
C8 C9 C10 118.58(16) . . ?
C9 O9 B 110.80(13) . . ?
N1 C10 C5 124.55(15) . . ?
N1 C10 C9 110.97(14) . . ?
C5 C10 C9 124.48(16) . . ?
C16 C11 C12 113.62(16) . . ?
C16 C11 B 126.53(16) . . ?
C12 C11 B 119.52(15) . . ?
F12 C12 C13 116.01(16) . . ?
F12 C12 C11 119.48(16) . . ?
C13 C12 C11 124.49(16) . . ?
F13 C13 C12 120.43(17) . . ?
F13 C13 C14 120.39(17) . . ?
C12 C13 C14 119.18(17) . . ?
F14 C14 C15 120.86(17) . . ?
F14 C14 C13 119.80(18) . . ?
C15 C14 C13 119.34(17) . . ?
F15 C15 C14 119.70(17) . . ?
F15 C15 C16 120.78(17) . . ?
C14 C15 C16 119.50(16) . . ?
F16 C16 C15 115.54(15) . . ?
F16 C16 C11 120.59(16) . . ?
C15 C16 C11 123.84(17) . . ?
C18 C17 C22 113.45(17) . . ?
C18 C17 B 121.29(15) . . ?
C22 C17 B 125.23(16) . . ?
F18 C18 C19 116.38(16) . . ?
F18 C18 C17 118.77(16) . . ?
C19 C18 C17 124.85(17) . . ?
F19 C19 C18 120.73(18) . . ?
F19 C19 C20 120.15(18) . . ?
C18 C19 C20 119.11(18) . . ?
F20 C20 C21 120.54(19) . . ?
F20 C20 C19 120.59(19) . . ?
C21 C20 C19 118.87(18) . . ?
F21 C21 C20 119.95(19) . . ?
F21 C21 C22 119.69(19) . . ?
C20 C21 C22 120.36(18) . . ?
F22 C22 C21 115.65(17) . . ?
F22 C22 C17 120.98(17) . . ?
C21 C22 C17 123.36(17) . . ?
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
B O9 1.494(2) . ?
B C11 1.624(3) . ?
B C17 1.629(3) . ?
B N1 1.637(2) . ?
N1 C2 1.328(2) . ?
N1 C10 1.363(2) . ?
C2 C3 1.403(3) . ?
C3 C4 1.366(3) . ?
C4 C5 1.411(3) . ?
C5 C10 1.398(2) . ?
C5 C6 1.414(3) . ?
C6 C7 1.369(3) . ?
C7 C8 1.415(3) . ?
C8 C9 1.363(2) . ?
C9 O9 1.349(2) . ?
C9 C10 1.402(2) . ?
C11 C16 1.388(2) . ?
C11 C12 1.390(2) . ?
C12 F12 1.357(2) . ?
C12 C13 1.375(3) . ?
C13 F13 1.343(2) . ?
C13 C14 1.378(3) . ?
C14 F14 1.342(2) . ?
C14 C15 1.370(3) . ?
C15 F15 1.334(2) . ?
C15 C16 1.387(3) . ?
C16 F16 1.343(2) . ?
C17 C18 1.390(2) . ?
C17 C22 1.391(3) . ?
C18 F18 1.358(2) . ?
C18 C19 1.374(3) . ?
C19 F19 1.339(2) . ?
C19 C20 1.375(3) . ?
C20 F20 1.339(2) . ?
C20 C21 1.371(3) . ?
C21 F21 1.346(2) . ?
C21 C22 1.380(3) . ?
C22 F22 1.347(2) . ?
