#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150459.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_7150459
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            'C30 H38 O'
_chemical_formula_weight         414.60
_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                 100.000(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3240(9)
_cell_length_b                   12.5501(7)
_cell_length_c                   14.623(1)
_cell_measurement_reflns_used    12613
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      21.0
_cell_measurement_theta_min      1.0
_cell_volume                     2588.8(3)
_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      228(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10312
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.9832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2198
_reflns_number_total             2786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209555f.txt
_cod_data_source_block           kor_2
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150459
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
O1 O 1.33711(17) 0.15040(19) 0.11292(16) 0.0988(8) Uani 1 1 d . . .
C1 C 1.28928(19) 0.1525(2) 0.1762(2) 0.0639(8) Uani 1 1 d . . .
C2 C 1.31408(17) 0.2252(2) 0.25578(19) 0.0571(7) Uani 1 1 d . . .
C3 C 1.25383(17) 0.2324(2) 0.31613(18) 0.0569(7) Uani 1 1 d . . .
H3 H 1.2699 0.2782 0.3673 0.068 Uiso 1 1 calc . . .
C4 C 1.16590(17) 0.17426(19) 0.30732(17) 0.0513(7) Uani 1 1 d . . .
C5 C 1.14887(17) 0.09644(19) 0.23455(18) 0.0509(7) Uani 1 1 d . . .
H5 H 1.0944 0.0536 0.2302 0.061 Uiso 1 1 calc . . .
C6 C 1.20644(18) 0.08127(19) 0.17219(17) 0.0527(7) Uani 1 1 d . . .
C7 C 1.10688(17) 0.1918(2) 0.37054(17) 0.0538(7) Uani 1 1 d . . .
H7 H 1.1329 0.2314 0.4234 0.065 Uiso 1 1 calc . . .
C21 C 1.40667(19) 0.2893(2) 0.2668(2) 0.0721(9) Uani 1 1 d . . .
C22 C 1.4228(2) 0.3528(3) 0.3572(3) 0.0979(11) Uani 1 1 d . . .
H22A H 1.4263 0.3043 0.4094 0.147 Uiso 1 1 calc . . .
H22B H 1.3706 0.4020 0.3573 0.147 Uiso 1 1 calc . . .
H22C H 1.4817 0.3923 0.3624 0.147 Uiso 1 1 calc . . .
C23 C 1.4914(2) 0.2130(3) 0.2677(3) 0.0997(12) Uani 1 1 d . . .
H23A H 1.4822 0.1720 0.2106 0.150 Uiso 1 1 calc . . .
H23B H 1.4957 0.1650 0.3202 0.150 Uiso 1 1 calc . . .
H23C H 1.5494 0.2541 0.2727 0.150 Uiso 1 1 calc . . .
C24 C 1.4014(3) 0.3674(3) 0.1855(3) 0.1005(12) Uani 1 1 d . . .
H24A H 1.3912 0.3282 0.1274 0.151 Uiso 1 1 calc . . .
H24B H 1.4604 0.4069 0.1913 0.151 Uiso 1 1 calc . . .
H24C H 1.3493 0.4167 0.1862 0.151 Uiso 1 1 calc . . .
C61 C 1.1904(2) -0.0073(2) 0.09904(18) 0.0643(8) Uani 1 1 d . . .
C62 C 1.1039(3) -0.0746(2) 0.1079(2) 0.0844(10) Uani 1 1 d . . .
H62A H 1.0481 -0.0295 0.1007 0.127 Uiso 1 1 calc . . .
H62B H 1.1133 -0.1082 0.1685 0.127 Uiso 1 1 calc . . .
H62C H 1.0953 -0.1290 0.0600 0.127 Uiso 1 1 calc . . .
C63 C 1.2770(3) -0.0806(3) 0.1107(3) 0.1027(12) Uani 1 1 d . . .
H63A H 1.3329 -0.0391 0.1052 0.154 Uiso 1 1 calc . . .
H63B H 1.2674 -0.1350 0.0628 0.154 Uiso 1 1 calc . . .
H63C H 1.2855 -0.1142 0.1713 0.154 Uiso 1 1 calc . . .
C64 C 1.1721(3) 0.0417(3) 0.0006(2) 0.0973(11) Uani 1 1 d . . .
H64A H 1.2258 0.0854 -0.0078 0.146 Uiso 1 1 calc . . .
H64B H 1.1154 0.0854 -0.0069 0.146 Uiso 1 1 calc . . .
H64C H 1.1636 -0.0149 -0.0453 0.146 Uiso 1 1 calc . . .
C3' C 1.01079(17) 0.15753(18) 0.36623(18) 0.0513(7) Uani 1 1 d . . .
C1' C 0.85531(19) 0.1278(2) 0.2988(2) 0.0660(8) Uani 1 1 d . A .
C2' C 0.94590(19) 0.1452(2) 0.28233(19) 0.0590(7) Uani 1 1 d . . .
H2' H 0.9624 0.1483 0.2229 0.071 Uiso 1 1 calc . . .
C4' C 0.9929(2) 0.14137(19) 0.5358(2) 0.0617(8) Uani 1 1 d . . .
C5' C 0.9356(3) 0.1318(2) 0.6046(2) 0.0876(11) Uani 1 1 d . . .
H5' H 0.9697 0.1315 0.6657 0.105 Uiso 1 1 calc . . .
C6' C 0.8381(4) 0.1227(3) 0.5992(4) 0.1175(17) Uani 1 1 d . A .
H6' H 0.8191 0.1198 0.6575 0.141 Uiso 1 1 calc . . .
C7' C 0.7644(3) 0.1171(3) 0.5266(4) 0.1089(16) Uani 1 1 d . . .
C8' C 0.7777(2) 0.1170(2) 0.4352(3) 0.0817(10) Uani 1 1 d . A .
H8' H 0.7216 0.1076 0.3918 0.098 Uiso 1 1 calc . . .
C9' C 0.85834(19) 0.12806(19) 0.3958(2) 0.0614(8) Uani 1 1 d . . .
C10' C 0.95856(17) 0.14548(18) 0.44029(19) 0.0510(7) Uani 1 1 d . A .
C11' C 0.7688(2) 0.1145(3) 0.2244(3) 0.1046(12) Uani 1 1 d . . .
H11A H 0.7836 0.1369 0.1650 0.157 Uiso 1 1 calc R A .
H11B H 0.7175 0.1579 0.2395 0.157 Uiso 1 1 calc R . .
H11C H 0.7496 0.0403 0.2209 0.157 Uiso 1 1 calc R . .
C41' C 1.0979(2) 0.1470(2) 0.5722(2) 0.0760(9) Uani 1 1 d . . .
H41A H 1.1317 0.1068 0.5316 0.114 Uiso 1 1 calc R . .
H41B H 1.1112 0.1170 0.6342 0.114 Uiso 1 1 calc R . .
H41C H 1.1184 0.2207 0.5741 0.114 Uiso 1 1 calc R . .
C71 C 0.6804(5) 0.1158(6) 0.5741(5) 0.068(2) Uani 0.50 1 d P A 1
H71 H 0.7046 0.1269 0.6411 0.081 Uiso 0.50 1 calc P B 1
C72 C 0.6132(2) 0.1987(3) 0.5457(3) 0.1142(14) Uani 0.50 1 d P A 1
H72A H 0.5609 0.1925 0.5795 0.171 Uiso 0.50 1 calc P C 1
H72B H 0.5894 0.1926 0.4796 0.171 Uiso 0.50 1 calc P D 1
H72C H 0.6436 0.2675 0.5586 0.171 Uiso 0.50 1 calc P E 1
C73 C 0.6371(2) 0.0016(3) 0.5643(3) 0.1117(13) Uani 0.50 1 d P A 1
H73A H 0.6864 -0.0504 0.5847 0.168 Uiso 0.50 1 calc P F 1
H73B H 0.6098 -0.0115 0.4998 0.168 Uiso 0.50 1 calc P G 1
H73C H 0.5881 -0.0043 0.6022 0.168 Uiso 0.50 1 calc P H 1
C71' C 0.6493(5) 0.0942(6) 0.5194(5) 0.0622(18) Uani 0.50 1 d P A 2
H71' H 0.6230 0.0828 0.4530 0.075 Uiso 0.50 1 calc P I 2
C72' C 0.6132(2) 0.1987(3) 0.5457(3) 0.1142(14) Uani 0.50 1 d P A 2
H72D H 0.6298 0.2536 0.5046 0.171 Uiso 0.50 1 calc P J 2
H72E H 0.6413 0.2155 0.6092 0.171 Uiso 0.50 1 calc P K 2
H72F H 0.5448 0.1954 0.5403 0.171 Uiso 0.50 1 calc P L 2
C73' C 0.6371(2) 0.0016(3) 0.5643(3) 0.1117(13) Uani 0.50 1 d P A 2
H73D H 0.6663 -0.0564 0.5357 0.168 Uiso 0.50 1 calc P M 2
H73E H 0.5699 -0.0124 0.5601 0.168 Uiso 0.50 1 calc P N 2
H73F H 0.6665 0.0077 0.6290 0.168 Uiso 0.50 1 calc P O 2
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'
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
O1 C1 C2 120.9(3) . . ?
O1 C1 C6 120.0(3) . . ?
C2 C1 C6 119.1(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C21 122.6(3) . . ?
C1 C2 C21 119.5(2) . . ?
C2 C3 C4 124.0(2) . . ?
C7 C4 C5 124.3(2) . . ?
C7 C4 C3 119.3(2) . . ?
C5 C4 C3 116.4(2) . . ?
C6 C5 C4 123.7(2) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C61 122.7(2) . . ?
C1 C6 C61 119.2(2) . . ?
C4 C7 C3' 128.4(2) . . ?
C22 C21 C24 108.5(3) . . ?
C22 C21 C2 111.2(2) . . ?
C24 C21 C2 109.2(3) . . ?
C22 C21 C23 108.4(3) . . ?
C24 C21 C23 109.6(3) . . ?
C2 C21 C23 109.8(2) . . ?
C62 C61 C63 108.2(3) . . ?
C62 C61 C6 111.7(2) . . ?
C63 C61 C6 109.8(2) . . ?
C62 C61 C64 106.9(3) . . ?
C63 C61 C64 110.2(3) . . ?
C6 C61 C64 110.0(2) . . ?
C2' C3' C10' 107.1(2) . . ?
C2' C3' C7 123.6(2) . . ?
C10' C3' C7 128.7(2) . . ?
C2' C1' C9' 108.0(3) . . ?
C2' C1' C11' 124.9(3) . . ?
C9' C1' C11' 127.1(3) . . ?
C1' C2' C3' 111.3(2) . . ?
C10' C4' C5' 124.7(3) . . ?
C10' C4' C41' 120.5(2) . . ?
C5' C4' C41' 114.9(3) . . ?
C6' C5' C4' 132.0(4) . . ?
C7' C6' C5' 133.2(4) . . ?
C6' C7' C8' 122.4(3) . . ?
C6' C7' C71 102.5(5) . . ?
C8' C7' C71 135.1(5) . . ?
C6' C7' C71' 133.2(4) . . ?
C8' C7' C71' 103.9(5) . . ?
C71 C7' C71' 32.1(3) . . ?
C7' C8' C9' 131.8(4) . . ?
C8' C9' C1' 122.4(3) . . ?
C8' C9' C10' 130.2(3) . . ?
C1' C9' C10' 107.4(2) . . ?
C4' C10' C3' 128.5(2) . . ?
C4' C10' C9' 125.2(2) . . ?
C3' C10' C9' 106.1(2) . . ?
C72 C71 C7' 114.4(5) . . ?
C72 C71 C73 113.9(5) . . ?
C7' C71 C73 107.9(5) . . ?
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 C1 1.243(3) . ?
C1 C2 1.473(4) . ?
C1 C6 1.479(4) . ?
C2 C3 1.340(3) . ?
C2 C21 1.536(4) . ?
C3 C4 1.442(3) . ?
C4 C7 1.374(3) . ?
C4 C5 1.434(3) . ?
C5 C6 1.345(3) . ?
C6 C61 1.532(4) . ?
C7 C3' 1.433(3) . ?
C21 C22 1.527(5) . ?
C21 C24 1.533(5) . ?
C21 C23 1.544(4) . ?
C61 C62 1.523(4) . ?
C61 C63 1.530(4) . ?
C61 C64 1.545(4) . ?
C3' C2' 1.413(4) . ?
C3' C10' 1.427(3) . ?
C1' C2' 1.378(4) . ?
C1' C9' 1.412(4) . ?
C1' C11' 1.510(4) . ?
C4' C10' 1.399(4) . ?
C4' C5' 1.410(4) . ?
C4' C41' 1.508(4) . ?
C5' C6' 1.390(6) . ?
C6' C7' 1.362(6) . ?
C7' C8' 1.382(6) . ?
C7' C71 1.491(8) . ?
C7' C71' 1.660(8) . ?
C8' C9' 1.384(4) . ?
C9' C10' 1.486(4) . ?
C71 C72 1.430(8) . ?
C71 C73 1.557(9) . ?
