#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:31:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180225 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/11/7111103.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111103
loop_
_publ_author_name
'Burke, Jacquelyn M.'
'Fox, Mark A.'
'Goeta, Andrés E.'
'Hughes, Andrew K.'
'Marder, Todd B.'
_publ_section_title
;
 Why are B2O2 rings rare?
;
_journal_issue                   22
_journal_name_full               'Chemical Communications'
_journal_page_first              2217
_journal_paper_doi               10.1039/b006685k
_journal_year                    2000
_chemical_formula_sum            'C18 H16 B2 F5 O P'
_chemical_formula_weight         395.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.688(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.638(3)
_cell_length_b                   12.174(3)
_cell_length_c                   13.542(3)
_cell_measurement_reflns_used    617
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.10
_cell_measurement_theta_min      13.80
_cell_volume                     1914.7(8)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998a)'
_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998a)'
_computing_data_reduction        'SAINT-NT V5.0 (Bruker, 1998b)'
_computing_molecular_graphics    'SHELXTL-NT V5.1 (Bruker, 1998c)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker SMART-CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22662
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0482
_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)+(0.0553P)²+1.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                3923
_reflns_number_total             5437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b006685ksup1.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1914.6(8)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7111103
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
H1P H 0.6516(18) 0.8099(18) 0.0665(16) 0.039(6) Uiso 1 1 d .
P1 P 0.69273(4) 0.73942(3) 0.12437(3) 0.02519(12) Uani 1 1 d .
C1 C 0.61611(15) 0.74317(14) 0.23419(13) 0.0274(4) Uani 1 1 d .
C2 C 0.50334(19) 0.7800(2) 0.22721(16) 0.0487(6) Uani 1 1 d .
H2 H 0.4705 0.8067 0.1675 0.058 Uiso 1 1 calc R
C3 C 0.4402(2) 0.7765(3) 0.3101(2) 0.0741(10) Uani 1 1 d .
H3 H 0.3638 0.7993 0.3060 0.089 Uiso 1 1 calc R
C4 C 0.4904(2) 0.7392(2) 0.39947(18) 0.0606(8) Uani 1 1 d .
H4 H 0.4474 0.7377 0.4550 0.073 Uiso 1 1 calc R
C5 C 0.6027(2) 0.70452(19) 0.40675(15) 0.0443(5) Uani 1 1 d .
H5 H 0.6361 0.6806 0.4672 0.053 Uiso 1 1 calc R
C6 C 0.66643(18) 0.70524(17) 0.32367(14) 0.0361(4) Uani 1 1 d .
H6 H 0.7422 0.6805 0.3278 0.043 Uiso 1 1 calc R
C7 C 0.67759(16) 0.60791(14) 0.06548(14) 0.0301(4) Uani 1 1 d .
C8 C 0.6349(2) 0.51840(16) 0.11493(16) 0.0418(5) Uani 1 1 d .
H8 H 0.6104 0.5267 0.1785 0.050 Uiso 1 1 calc R
C9 C 0.6288(2) 0.41654(18) 0.06916(18) 0.0508(6) Uani 1 1 d .
H9 H 0.6006 0.3563 0.1022 0.061 Uiso 1 1 calc R
C10 C 0.6645(2) 0.40442(18) -0.02478(19) 0.0513(6) Uani 1 1 d .
H10 H 0.6618 0.3355 -0.0545 0.062 Uiso 1 1 calc R
C11 C 0.7045(2) 0.4939(2) -0.07586(19) 0.0560(7) Uani 1 1 d .
H11 H 0.7271 0.4854 -0.1400 0.067 Uiso 1 1 calc R
C12 C 0.7107(2) 0.59653(18) -0.03068(17) 0.0471(5) Uani 1 1 d .
H12 H 0.7367 0.6571 -0.0646 0.057 Uiso 1 1 calc R
C13 C 0.84179(15) 0.77208(14) 0.14759(13) 0.0274(4) Uani 1 1 d .
C14 C 0.87832(16) 0.88052(15) 0.13719(14) 0.0323(4) Uani 1 1 d .
H14 H 0.8258 0.9352 0.1179 0.039 Uiso 1 1 calc R
C15 C 0.99403(18) 0.90569(19) 0.15597(16) 0.0411(5) Uani 1 1 d .
H15 H 1.0194 0.9774 0.1480 0.049 Uiso 1 1 calc R
C16 C 1.07124(18) 0.8250(2) 0.18624(16) 0.0453(5) Uani 1 1 d .
H16 H 1.1484 0.8429 0.1996 0.054 Uiso 1 1 calc R
C17 C 1.03524(19) 0.7176(2) 0.19696(17) 0.0491(6) Uani 1 1 d .
H17 H 1.0882 0.6637 0.2174 0.059 Uiso 1 1 calc R
C18 C 0.92044(18) 0.69015(18) 0.17722(16) 0.0398(5) Uani 1 1 d .
H18 H 0.8961 0.6179 0.1837 0.048 Uiso 1 1 calc R
F1 F 1.20413(12) 0.63868(11) 0.40271(10) 0.0513(3) Uani 1 1 d .
F2 F 1.15747(12) 0.49332(10) 0.30539(9) 0.0467(3) Uani 1 1 d .
F3 F 1.26426(12) 0.46864(15) 0.44982(11) 0.0675(5) Uani 1 1 d .
B1 B 1.17819(19) 0.52808(19) 0.40129(16) 0.0332(5) Uani 1 1 d .
O1 O 1.07138(11) 0.51062(10) 0.45721(9) 0.0303(3) Uani 1 1 d .
B2 B 0.95042(17) 0.55344(16) 0.45080(15) 0.0263(4) Uani 1 1 d .
F4 F 0.94367(11) 0.66415(8) 0.46373(9) 0.0410(3) Uani 1 1 d .
F5 F 0.88552(10) 0.51894(9) 0.36939(8) 0.0355(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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 P1 C13 112.28(9) . .
C1 P1 C7 110.72(8) . .
C13 P1 C7 110.09(8) . .
C1 P1 H1P 108.4(10) . .
C13 P1 H1P 106.8(10) . .
C7 P1 H1P 108.3(10) . .
C2 C1 C6 120.76(17) . .
C2 C1 P1 118.30(14) . .
C6 C1 P1 120.87(14) . .
C3 C2 C1 119.1(2) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 120.3(2) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 120.6(2) . .
C5 C4 H4 119.7 . .
C3 C4 H4 119.7 . .
C4 C5 C6 119.8(2) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 119.47(18) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
C8 C7 C12 120.25(18) . .
C8 C7 P1 120.99(15) . .
C12 C7 P1 118.76(14) . .
C9 C8 C7 119.8(2) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C10 C9 C8 120.1(2) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C11 120.6(2) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C10 C11 C12 119.7(2) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C7 C12 C11 119.5(2) . .
C7 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C18 C13 C14 120.43(18) . .
C18 C13 P1 120.18(15) . .
C14 C13 P1 119.38(14) . .
C15 C14 C13 119.21(18) . .
C15 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
C16 C15 C14 120.3(2) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C15 C16 C17 120.6(2) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C16 C17 C18 120.1(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C13 119.3(2) . .
C17 C18 H18 120.3 . .
C13 C18 H18 120.3 . .
F3 B1 F2 111.71(17) . .
F3 B1 F1 110.9(2) . .
F2 B1 F1 109.82(17) . .
F3 B1 O1 106.56(16) . .
F2 B1 O1 109.31(17) . .
F1 B1 O1 108.45(15) . .
B2 O1 B2 91.17(12) . 3_766
B2 O1 B1 136.21(14) . .
B2 O1 B1 132.48(14) 3_766 .
F5 B2 F4 112.06(15) . .
F5 B2 O1 114.18(15) . .
F4 B2 O1 113.49(16) . .
F5 B2 O1 113.33(15) . 3_766
F4 B2 O1 113.09(15) . 3_766
O1 B2 O1 88.83(12) . 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.7832(17) .
P1 C13 1.7877(19) .
P1 C7 1.7922(19) .
P1 H1P 1.24(2) .
C1 C2 1.384(3) .
C1 C6 1.390(3) .
C2 C3 1.381(3) .
C2 H2 0.9300 .
C3 C4 1.385(4) .
C3 H3 0.9300 .
C4 C5 1.372(3) .
C4 H4 0.9300 .
C5 C6 1.387(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.388(3) .
C7 C12 1.388(3) .
C8 C9 1.386(3) .
C8 H8 0.9300 .
C9 C10 1.371(3) .
C9 H9 0.9300 .
C10 C11 1.387(3) .
C10 H10 0.9300 .
C11 C12 1.391(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C18 1.395(3) .
C13 C14 1.397(3) .
C14 C15 1.388(3) .
C14 H14 0.9300 .
C15 C16 1.376(3) .
C15 H15 0.9300 .
C16 C17 1.384(4) .
C16 H16 0.9300 .
C17 C18 1.386(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
F1 B1 1.380(3) .
F2 B1 1.372(2) .
F3 B1 1.369(3) .
B1 O1 1.512(2) .
O1 B2 1.498(2) .
O1 B2 1.505(2) 3_766
B2 F5 1.362(2) .
B2 F4 1.362(2) .
B2 O1 1.505(2) 3_766
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C13 P1 C1 C2 144.73(17) . .
C7 P1 C1 C2 -91.77(19) . .
C13 P1 C1 C6 -38.26(19) . .
C7 P1 C1 C6 85.24(18) . .
C6 C1 C2 C3 -1.3(4) . .
P1 C1 C2 C3 175.7(2) . .
C1 C2 C3 C4 1.6(5) . .
C2 C3 C4 C5 -0.5(5) . .
C3 C4 C5 C6 -0.9(5) . .
C4 C5 C6 C1 1.2(4) . .
C2 C1 C6 C5 -0.1(3) . .
P1 C1 C6 C5 -177.02(17) . .
C1 P1 C7 C8 -13.9(2) . .
C13 P1 C7 C8 110.84(18) . .
C1 P1 C7 C12 166.80(17) . .
C13 P1 C7 C12 -68.44(19) . .
C12 C7 C8 C9 2.1(3) . .
P1 C7 C8 C9 -177.17(18) . .
C7 C8 C9 C10 -0.3(4) . .
C8 C9 C10 C11 -1.4(4) . .
C9 C10 C11 C12 1.3(4) . .
C8 C7 C12 C11 -2.2(4) . .
P1 C7 C12 C11 177.0(2) . .
C10 C11 C12 C7 0.6(4) . .
C1 P1 C13 C18 85.83(17) . .
C7 P1 C13 C18 -38.03(18) . .
C1 P1 C13 C14 -93.24(16) . .
C7 P1 C13 C14 142.91(15) . .
C18 C13 C14 C15 0.5(3) . .
P1 C13 C14 C15 179.55(14) . .
C13 C14 C15 C16 -1.2(3) . .
C14 C15 C16 C17 1.0(3) . .
C15 C16 C17 C18 0.0(3) . .
C16 C17 C18 C13 -0.7(3) . .
C14 C13 C18 C17 0.5(3) . .
P1 C13 C18 C17 -178.60(16) . .
F3 B1 O1 B2 175.83(19) . .
F2 B1 O1 B2 -63.3(3) . .
F1 B1 O1 B2 56.4(3) . .
F3 B1 O1 B2 1.4(3) . 3_766
F2 B1 O1 B2 122.3(2) . 3_766
F1 B1 O1 B2 -118.0(2) . 3_766
B2 O1 B2 F5 -115.15(18) 3_766 .
B1 O1 B2 F5 69.0(3) . .
B2 O1 B2 F4 114.75(19) 3_766 .
B1 O1 B2 F4 -61.1(3) . .
B2 O1 B2 O1 0.0 3_766 3_766
B1 O1 B2 O1 -175.9(2) . 3_766
