#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150458.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_7150458
loop_
_publ_author_name
'Laus, Gerhard'
'Schottenberger, Herwig'
'Wurst, Klaus'
'Schütz, Johannes'
'Ongania, Karl-Hans'
'Horvath, Ulrike Erika Ida'
'Schwärzler, Alexander'
_publ_section_title
;
 Solvatochromism, halochromism, and preferential solvation of new
 dipolar guaiazulenyl 1,4-benzoquinone methidesElectronic supplementary
 information (ESI) available: Absorption maxima of the dyes 6--10 in
 seven binary solvent mixtures. See
 http://www.rsc.org/suppdata/ob/b2/b209555f/
;
_journal_issue                   8
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1409
_journal_paper_doi               10.1039/b209555f
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C22 H23 B F4 O'
_chemical_formula_weight         390.21
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 105.737(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8532(7)
_cell_length_b                   6.9944(5)
_cell_length_c                   14.504(1)
_cell_measurement_reflns_used    6066
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      1.0
_cell_volume                     962.11(12)
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4286
_diffrn_reflns_theta_full        21.48
_diffrn_reflns_theta_max         21.48
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    'mixed; refined at O1'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0423
_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)+(0.0497P)²+0.4065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                945
_reflns_number_total             1215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209555f.txt
_cod_data_source_block           kor
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               7150458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_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
O1 O 0.9230(3) 0.2500 0.31279(18) 0.0572(8) Uani 1 2 d S . .
H1O H 0.829(5) 0.2500 0.314(3) 0.081(15) Uiso 1 2 d S . .
C1 C 0.9407(4) 0.2500 0.2229(3) 0.0424(10) Uani 1 2 d S . .
C2 C 0.8296(4) 0.2500 0.1421(3) 0.0501(11) Uani 1 2 d S . .
H2 H 0.7365 0.2500 0.1472 0.060 Uiso 1 2 calc S . .
C3 C 0.8551(4) 0.2500 0.0534(3) 0.0512(11) Uani 1 2 d S . .
H3 H 0.7776 0.2500 -0.0012 0.061 Uiso 1 2 calc S . .
C4 C 0.9899(4) 0.2500 0.0407(3) 0.0416(10) Uani 1 2 d S . .
C5 C 1.1011(4) 0.2500 0.1242(3) 0.0464(10) Uani 1 2 d S . .
H5 H 1.1943 0.2500 0.1193 0.056 Uiso 1 2 calc S . .
C6 C 1.0777(4) 0.2500 0.2135(3) 0.0487(11) Uani 1 2 d S . .
H6 H 1.1547 0.2500 0.2685 0.058 Uiso 1 2 calc S . .
C7 C 0.9983(4) 0.2500 -0.0570(3) 0.0448(10) Uani 1 2 d S . .
H7 H 0.9096 0.2500 -0.1023 0.054 Uiso 1 2 calc S . .
C1' C 1.3371(4) 0.2500 -0.1083(2) 0.0453(10) Uani 1 2 d S . .
C2' C 1.2559(4) 0.2500 -0.0475(3) 0.0500(11) Uani 1 2 d S . .
H2' H 1.2913 0.2500 0.0195 0.060 Uiso 1 2 calc S . .
C3' C 1.1083(4) 0.2500 -0.0974(2) 0.0396(9) Uani 1 2 d S . .
C4' C 0.9822(4) 0.2500 -0.2796(3) 0.0416(10) Uani 1 2 d S . .
C5' C 0.9881(4) 0.2500 -0.3758(3) 0.0504(11) Uani 1 2 d S . .
H5' H 0.8983 0.2500 -0.4199 0.061 Uiso 1 2 calc S . .
C6' C 1.0958(4) 0.2500 -0.4193(3) 0.0534(11) Uani 1 2 d S . .
H6' H 1.0662 0.2500 -0.4866 0.064 Uiso 1 2 calc S . .
C7' C 1.2408(4) 0.2500 -0.3805(3) 0.0449(10) Uani 1 2 d S . .
C8' C 1.3047(4) 0.2500 -0.2835(3) 0.0455(10) Uani 1 2 d S . .
H8' H 1.4038 0.2500 -0.2669 0.055 Uiso 1 2 calc S . .
C9' C 1.2464(4) 0.2500 -0.2052(3) 0.0419(10) Uani 1 2 d S . .
C10' C 1.1007(4) 0.2500 -0.2010(2) 0.0382(9) Uani 1 2 d S . .
C11' C 1.4948(4) 0.2500 -0.0819(3) 0.0650(13) Uani 1 2 d S . .
H11A H 1.5275 0.1456 -0.1144 0.098 Uiso 0.50 1 calc PR . .
H11B H 1.5313 0.2341 -0.0131 0.098 Uiso 0.50 1 calc PR . .
H11C H 1.5280 0.3704 -0.1010 0.098 Uiso 0.50 1 calc PR . .
C41' C 0.8327(3) 0.2500 -0.2702(3) 0.0519(11) Uani 1 2 d S . .
H41A H 0.8224 0.1487 -0.2269 0.078 Uiso 0.50 1 calc PR . .
H41B H 0.7672 0.2290 -0.3326 0.078 Uiso 0.50 1 calc PR . .
H41C H 0.8130 0.3722 -0.2450 0.078 Uiso 0.50 1 calc PR . .
C71' C 1.3343(4) 0.2500 -0.4486(3) 0.0551(11) Uani 1 2 d S . .
H71' H 1.4338 0.2500 -0.4096 0.066 Uiso 1 2 calc S . .
C72' C 1.3100(3) 0.0709(5) -0.5102(2) 0.0673(9) Uani 1 1 d . . .
H72A H 1.3261 -0.0412 -0.4693 0.101 Uiso 1 1 calc . . .
H72B H 1.3746 0.0698 -0.5501 0.101 Uiso 1 1 calc . . .
H72C H 1.2137 0.0698 -0.5505 0.101 Uiso 1 1 calc . . .
B1 B 0.5017(5) 0.2500 0.2574(3) 0.0556(13) Uani 1 2 d S . .
F1 F 0.6443(2) 0.2500 0.30808(17) 0.0818(9) Uani 1 2 d S . .
F2 F 0.4925(3) 0.2500 0.16261(18) 0.1049(11) Uani 1 2 d S . .
F3 F 0.4382(2) 0.0919(3) 0.28079(16) 0.1084(8) 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'
O O 0.0106 0.0060 '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'
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
H1O O1 C1 114(3) . . ?
O1 C1 C2 122.7(3) . . ?
O1 C1 C6 118.2(3) . . ?
C2 C1 C6 119.1(3) . . ?
C1 C2 C3 119.6(3) . . ?
C2 C3 C4 123.2(4) . . ?
C3 C4 C5 116.0(3) . . ?
C3 C4 C7 116.3(3) . . ?
C5 C4 C7 127.8(3) . . ?
C6 C5 C4 121.6(3) . . ?
C5 C6 C1 120.4(3) . . ?
C3' C7 C4 133.3(3) . . ?
C2' C1' C9' 108.5(3) . . ?
C2' C1' C11' 126.5(3) . . ?
C9' C1' C11' 125.1(3) . . ?
C1' C2' C3' 111.8(3) . . ?
C7 C3' C2' 126.7(3) . . ?
C7 C3' C10' 127.3(3) . . ?
C2' C3' C10' 106.0(3) . . ?
C10' C4' C5' 124.0(3) . . ?
C10' C4' C41' 123.0(3) . . ?
C5' C4' C41' 113.0(3) . . ?
C6' C5' C4' 134.2(3) . . ?
C5' C6' C7' 130.7(4) . . ?
C8' C7' C6' 123.4(3) . . ?
C8' C7' C71' 118.3(3) . . ?
C6' C7' C71' 118.3(3) . . ?
C7' C8' C9' 130.7(3) . . ?
C8' C9' C1' 120.3(3) . . ?
C8' C9' C10' 131.2(3) . . ?
C1' C9' C10' 108.5(3) . . ?
C4' C10' C9' 125.7(3) . . ?
C4' C10' C3' 129.0(3) . . ?
C9' C10' C3' 105.3(3) . . ?
C72' C71' C72' 111.0(3) . 4_565 ?
C72' C71' C7' 110.8(2) . . ?
C72' C71' C7' 110.8(2) 4_565 . ?
F2 B1 F3 110.2(3) . . ?
F2 B1 F3 110.2(3) . 4_565 ?
F3 B1 F3 109.0(4) . 4_565 ?
F2 B1 F1 108.4(3) . . ?
F3 B1 F1 109.5(3) . . ?
F3 B1 F1 109.5(3) 4_565 . ?
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
O1 H1O 0.93(5) . ?
O1 C1 1.361(4) . ?
C1 C2 1.370(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.376(5) . ?
C3 C4 1.390(5) . ?
C4 C5 1.396(5) . ?
C4 C7 1.442(5) . ?
C5 C6 1.376(5) . ?
C7 C3' 1.364(5) . ?
C1' C2' 1.342(5) . ?
C1' C9' 1.446(5) . ?
C1' C11' 1.496(5) . ?
C2' C3' 1.438(5) . ?
C3' C10' 1.484(5) . ?
C4' C10' 1.393(5) . ?
C4' C5' 1.412(5) . ?
C4' C41' 1.516(5) . ?
C5' C6' 1.374(5) . ?
C6' C7' 1.387(5) . ?
C7' C8' 1.376(5) . ?
C7' C71' 1.522(5) . ?
C8' C9' 1.405(5) . ?
C9' C10' 1.453(5) . ?
C71' C72' 1.520(4) . ?
C71' C72' 1.520(4) 4_565 ?
B1 F2 1.353(5) . ?
B1 F3 1.358(3) . ?
B1 F3 1.358(3) 4_565 ?
B1 F1 1.398(5) . ?
