#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:36:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180087 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/33/7053362.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_7053362
loop_
_publ_author_name
'Kurjatschij, Sandra'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Synthesis and structures of crystalline solvates formed of pyridinium
 N-phenoxide (Reichardt's-type) betaine dyes and alcohols
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1465
_journal_paper_doi               10.1039/b9nj00540d
_journal_volume                  34
_journal_year                    2010
_chemical_formula_moiety         'C43 H33 N O, C3 H8 O'
_chemical_formula_sum            'C46 H41 N O2'
_chemical_formula_weight         639.80
_chemical_name_common
;
2,6-Di(3-methylphenyl)-4-(2,4,6-triphenyl-1-pyridino)-
phenolat-Isopropanol (1:1)
;
_chemical_name_systematic
;
2,6-Di(3-methylphenyl)-4-(2,4,6-triphenyl-1-pyridino)-phenolat-
Isopropanol (1:1)
;
_space_group_IT_number           167
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-P 3* 2n'
_symmetry_space_group_name_H-M   'R -3 c :R'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.15(1)
_cell_angle_beta                 104.15(1)
_cell_angle_gamma                104.15(1)
_cell_formula_units_Z            6
_cell_length_a                   18.822(1)
_cell_length_b                   18.822(1)
_cell_length_c                   18.822(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      45
_cell_measurement_theta_min      40
_cell_volume                     5932.3(9)
_computing_cell_refinement       CAD4-Express
_computing_data_collection       CAD4-Express
_computing_data_reduction        'XCAD4 (Sheldrick & Harms, 1992)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       two-theta/omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10111
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        12
_diffrn_standards_interval_count '200 (orientation)'
_diffrn_standards_interval_time  '120 min. (intensity)'
_diffrn_standards_number         '2 (orientation), 3 (intensity)'
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   psi-scans
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0559
_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)+(0.1303P)²+0.0607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                2119
_reflns_number_total             3361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00540d.txt
_cod_data_source_block           we10cu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_sg_symbol_H-M      'R -3 c'
_cod_database_code               7053362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-y+1/2, -x+1/2, -z+1/2'
'-x+1/2, -z+1/2, -y+1/2'
'-z+1/2, -y+1/2, -x+1/2'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'
'y-1/2, x-1/2, z-1/2'
'x-1/2, z-1/2, y-1/2'
'z-1/2, y-1/2, x-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 0.35557(6) 0.7500 0.14443(6) 0.0609(6) Uani 1 2 d S . .
C1 C 0.31286(9) 0.7500 0.18714(9) 0.0480(7) Uani 1 2 d S . .
C2 C 0.33875(10) 0.74783(10) 0.26485(10) 0.0478(5) Uani 1 1 d . . .
C3 C 0.29127(11) 0.74789(11) 0.31043(11) 0.0530(5) Uani 1 1 d . . .
H3 H 0.3096 0.7465 0.3605 0.064 Uiso 1 1 calc R . .
C4 C 0.21723(9) 0.7500 0.28277(9) 0.0516(7) Uani 1 2 d S . .
N5 N 0.16800(7) 0.7500 0.33200(7) 0.0501(6) Uani 1 2 d S . .
C6 C 0.09636(11) 0.69466(11) 0.30654(11) 0.0505(5) Uani 1 1 d . . .
C7 C 0.04878(11) 0.69785(11) 0.35089(11) 0.0534(5) Uani 1 1 d . . .
H7 H -0.0020 0.6644 0.3307 0.064 Uiso 1 1 calc R . .
C8 C 0.07449(9) 0.7500 0.42551(9) 0.0505(7) Uani 1 2 d S . .
C9 C 0.02467(9) 0.7500 0.47533(9) 0.0536(7) Uani 1 2 d S . .
C10 C -0.05504(12) 0.72985(13) 0.44334(13) 0.0664(6) Uani 1 1 d . . .
H10 H -0.0777 0.7156 0.3900 0.080 Uiso 1 1 calc R . .
C11 C -0.10066(14) 0.73097(16) 0.49068(16) 0.0828(8) Uani 1 1 d . . .
H11 H -0.1539 0.7186 0.4689 0.099 Uiso 1 1 calc R . .
C12 C -0.06877(12) 0.7500 0.56877(12) 0.0881(12) Uani 1 2 d S . .
H12 H -0.1001 0.7500 0.6001 0.106 Uiso 1 2 calc SR . .
C13 C 0.41728(11) 0.74273(12) 0.29709(11) 0.0527(5) Uani 1 1 d . . .
C14 C 0.47839(12) 0.80647(14) 0.34908(14) 0.0726(7) Uani 1 1 d . . .
H14 H 0.4715 0.8547 0.3622 0.087 Uiso 1 1 calc R . .
C15 C 0.54921(14) 0.79922(18) 0.38152(16) 0.0878(8) Uani 1 1 d . . .
H15 H 0.5902 0.8427 0.4152 0.105 Uiso 1 1 calc R . .
C16 C 0.55918(14) 0.7282(2) 0.36414(16) 0.0867(8) Uani 1 1 d . . .
H16 H 0.6065 0.7235 0.3880 0.104 Uiso 1 1 calc R . .
C17 C 0.50077(15) 0.66396(16) 0.31219(18) 0.0860(8) Uani 1 1 d . . .
C18 C 0.5114(2) 0.5853(2) 0.2918(4) 0.163(2) Uani 1 1 d . . .
H18A H 0.4932 0.5618 0.2365 0.245 Uiso 1 1 calc R . .
H18B H 0.4823 0.5530 0.3142 0.245 Uiso 1 1 calc R . .
H18C H 0.5652 0.5910 0.3117 0.245 Uiso 1 1 calc R . .
C19 C 0.43032(13) 0.67294(14) 0.27938(16) 0.0748(7) Uani 1 1 d . . .
H19 H 0.3902 0.6297 0.2439 0.090 Uiso 1 1 calc R . .
C20 C 0.07146(12) 0.62909(11) 0.23291(11) 0.0548(5) Uani 1 1 d . . .
C21 C -0.00056(12) 0.61052(14) 0.18008(12) 0.0654(6) Uani 1 1 d . . .
H21 H -0.0326 0.6397 0.1895 0.078 Uiso 1 1 calc R . .
C22 C -0.02527(15) 0.54791(16) 0.11250(14) 0.0809(8) Uani 1 1 d . . .
H22 H -0.0735 0.5360 0.0761 0.097 Uiso 1 1 calc R . .
C23 C 0.02077(16) 0.50381(16) 0.09927(15) 0.0866(9) Uani 1 1 d . . .
H23 H 0.0040 0.4620 0.0540 0.104 Uiso 1 1 calc R . .
C24 C 0.09192(17) 0.52114(15) 0.15283(16) 0.0882(8) Uani 1 1 d . . .
H24 H 0.1227 0.4903 0.1441 0.106 Uiso 1 1 calc R . .
C25 C 0.11799(14) 0.58351(14) 0.21919(14) 0.0727(7) Uani 1 1 d . . .
H25 H 0.1666 0.5953 0.2549 0.087 Uiso 1 1 calc R . .
C1P C 0.1389(12) 0.3691(15) 0.2351(16) 0.441(14) Uiso 0.50 1 d PDU A -1
H1P H 0.1206 0.4015 0.2062 0.529 Uiso 0.50 1 calc PR A -1
C2P C 0.0789(13) 0.2848(10) 0.2294(15) 0.380(12) Uiso 0.50 1 d PDU A -1
H2P1 H 0.0501 0.2557 0.1761 0.570 Uiso 0.50 1 calc PR A -1
H2P2 H 0.0438 0.2942 0.2571 0.570 Uiso 0.50 1 calc PR A -1
H2P3 H 0.1084 0.2560 0.2517 0.570 Uiso 0.50 1 calc PR A -1
C3P C 0.1809(11) 0.4041(11) 0.3309(10) 0.312(9) Uiso 0.50 1 d PDU A -1
H3P1 H 0.2193 0.4537 0.3446 0.468 Uiso 0.50 1 calc PR A -1
H3P2 H 0.2052 0.3691 0.3479 0.468 Uiso 0.50 1 calc PR A -1
H3P3 H 0.1426 0.4096 0.3554 0.468 Uiso 0.50 1 calc PR A -1
O1P O 0.2088(8) 0.3314(10) 0.2174(8) 0.328(6) Uiso 0.50 1 d PDU A -1
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'
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'
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
O1 C1 C2 122.33(12) . .
O1 C1 C2 122.33(11) . 6_565
C2 C1 C2 115.3(2) . 6_565
C2 C3 H3 119.5 . .
C4 C3 H3 119.6 . .
C3 C2 C1 121.39(18) . .
C3 C2 C13 118.40(17) . .
C1 C2 C13 120.18(17) . .
C4 C3 C2 120.94(19) . .
C3 C4 C3 120.0(2) . 6_565
C3 C4 N5 120.0 . .
C3 C4 N5 120.0(2) 6_565 .
C6 N5 C6 120.1(2) 6_565 .
C6 N5 C4 119.95(11) 6_565 .
C6 N5 C4 119.95(11) . .
C6 C7 H7 119.3 . .
C8 C7 H7 119.2 . .
C7 C6 N5 119.56(17) . .
C7 C6 C20 119.68(17) . .
N5 C6 C20 120.70(17) . .
C6 C7 C8 121.53(18) . .
C7 C8 C7 117.0(2) 6_565 .
C7 C8 C9 121.50(12) 6_565 .
C7 C8 C9 121.50(12) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C10 C9 C10 118.6(3) 6_565 .
C10 C9 C8 120.70(13) 6_565 .
C10 C9 C8 120.70(13) . .
C10 C11 H11 119.5 . .
C12 C11 H11 119.6 . .
C11 C10 C9 120.0(2) . .
C12 C11 C10 120.9(3) . .
C11 C12 C11 119.5(3) 6_565 .
C11 C12 H12 120.2 . .
C19 C13 C14 117.4(2) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.7 . .
C19 C13 C2 120.53(18) . .
C14 C13 C2 121.94(19) . .
C14 C15 H15 119.9 . .
C16 C15 H15 120.1 . .
C15 C14 C13 120.8(2) . .
C15 C16 H16 119.4 . .
C17 C16 H16 119.5 . .
C16 C15 C14 120.0(2) . .
C15 C16 C17 121.1(2) . .
C16 C17 C19 117.8(2) . .
C16 C17 C18 121.6(3) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
C19 C17 C18 120.6(3) . .
H18A C18 H18B 109.3 . .
H18A C18 H18C 109.6 . .
H18B C18 H18C 109.5 . .
C13 C19 C17 122.9(2) . .
C13 C19 H19 118.6 . .
C17 C19 H19 118.6 . .
C20 C21 C22 119.7(2) . .
C20 C21 H21 120.1 . .
C21 C20 C25 119.5(2) . .
C21 C20 C6 119.31(19) . .
C25 C20 C6 121.02(18) . .
C22 C21 H21 120.2 . .
C21 C22 H22 119.8 . .
C23 C22 H22 119.8 . .
C23 C22 C21 120.4(2) . .
C22 C23 H23 120.1 . .
C24 C23 H23 120.0 . .
C22 C23 C24 120.0(2) . .
C23 C24 H24 119.7 . .
C25 C24 H24 119.7 . .
C25 C24 C23 120.6(3) . .
C24 C25 H25 120.1 . .
C20 C25 H25 120.1 . .
C24 C25 C20 119.8(2) . .
C3P C1P C2P 98(2) . .
C1P C2P H2P1 109.4 . .
C1P C2P H2P2 109.5 . .
C1P C2P H2P3 109.4 . .
C1P C3P H3P1 109.5 . .
C1P C3P H3P2 109.5 . .
C1P C3P H3P3 109.6 . .
C2P C1P H1P 120.9 . .
C3P C1P H1P 120.9 . .
H2P1 C2P H2P2 109.5 . .
H2P1 C2P H2P3 109.5 . .
H2P2 C2P H2P3 109.5 . .
C3P C1P O1P 95.1(19) . .
H3P1 C3P H3P2 109.4 . .
H3P1 C3P H3P3 109.5 . .
H3P2 C3P H3P3 109.5 . .
C2P C1P O1P 94.4(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.268(3) .
C1 C2 1.438(2) .
C1 C2 1.438(2) 6_565
C2 C3 1.382(3) .
C2 C13 1.490(3) .
C3 C4 1.377(2) .
C3 H3 0.9300 .
C4 C3 1.377(2) 6_565
C4 N5 1.462(3) .
N5 C6 1.373(2) 6_565
N5 C6 1.373(2) .
C6 C7 1.367(3) .
C6 C20 1.492(3) .
C7 C8 1.390(2) .
C7 H7 0.9300 .
C8 C7 1.390(2) 6_565
C8 C9 1.479(4) .
C9 C10 1.388(3) 6_565
C9 C10 1.388(3) .
C10 C11 1.380(3) .
C10 H10 0.9300 .
C11 C12 1.362(3) .
C11 H11 0.9300 .
C12 C11 1.362(3) 6_565
C12 H12 0.9300 .
C13 C19 1.371(3) .
C13 C14 1.386(3) .
C14 C15 1.378(3) .
C14 H14 0.9300 .
C15 C16 1.366(4) .
C15 H15 0.9300 .
C16 C17 1.369(4) .
C16 H16 0.9300 .
C17 C19 1.389(3) .
C19 H19 0.9300 .
C17 C18 1.512(4) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C20 C21 1.374(3) .
C20 C25 1.392(3) .
C21 C22 1.390(3) .
C21 H21 0.9300 .
C22 C23 1.363(4) .
C22 H22 0.9300 .
C23 C24 1.372(4) .
C23 H23 0.9300 .
C24 C25 1.371(3) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C1P C3P 1.67(2) .
C1P H1P 0.9800 .
C1P C2P 1.67(2) .
C2P H2P1 0.9600 .
C2P H2P2 0.9600 .
C2P H2P3 0.9600 .
C1P O1P 1.703(19) .
C3P H3P1 0.9600 .
C3P H3P2 0.9600 .
C3P H3P3 0.9600 .
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
O1 C1 C2 C3 179.98(13) . .
C2 C1 C2 C3 -0.02(13) 6_565 .
O1 C1 C2 C13 -2.10(19) . .
C2 C1 C2 C13 177.90(19) 6_565 .
C1 C2 C3 C4 0.0(3) . .
C13 C2 C3 C4 -177.91(15) . .
C2 C3 C4 C3 -0.02(13) . 6_565
C2 C3 C4 N5 179.98(13) . .
C3 C4 N5 C6 55.17(13) . 6_565
C3 C4 N5 C6 -124.83(13) 6_565 6_565
C3 C4 N5 C6 -124.83(13) . .
C3 C4 N5 C6 55.17(13) 6_565 .
C6 N5 C6 C7 3.95(13) 6_565 .
C4 N5 C6 C7 -176.05(13) . .
C6 N5 C6 C20 -173.1(2) 6_565 .
C4 N5 C6 C20 6.9(2) . .
N5 C6 C7 C8 -8.0(3) . .
C20 C6 C7 C8 169.05(16) . .
C6 C7 C8 C7 4.05(13) . 6_565
C6 C7 C8 C9 -175.95(13) . .
C7 C8 C9 C10 -32.50(16) 6_565 6_565
C7 C8 C9 C10 147.50(16) . 6_565
C7 C8 C9 C10 147.50(16) 6_565 .
C7 C8 C9 C10 -32.50(16) . .
C10 C9 C10 C11 0.73(18) 6_565 .
C8 C9 C10 C11 -179.27(18) . .
C9 C10 C11 C12 -1.5(4) . .
C10 C11 C12 C11 0.75(18) . 6_565
C3 C2 C13 C19 97.4(3) . .
C1 C2 C13 C19 -80.6(2) . .
C3 C2 C13 C14 -78.8(3) . .
C1 C2 C13 C14 103.2(2) . .
C19 C13 C14 C15 -0.2(4) . .
C2 C13 C14 C15 176.1(2) . .
C13 C14 C15 C16 -1.8(4) . .
C14 C15 C16 C17 2.8(5) . .
C15 C16 C17 C19 -1.8(4) . .
C15 C16 C17 C18 179.3(4) . .
C14 C13 C19 C17 1.2(4) . .
C2 C13 C19 C17 -175.2(2) . .
C16 C17 C19 C13 -0.2(4) . .
C18 C17 C19 C13 178.7(4) . .
C7 C6 C20 C21 50.4(3) . .
N5 C6 C20 C21 -132.5(2) . .
C7 C6 C20 C25 -125.5(2) . .
N5 C6 C20 C25 51.6(3) . .
C25 C20 C21 C22 -1.9(3) . .
C6 C20 C21 C22 -177.9(2) . .
C20 C21 C22 C23 1.6(4) . .
C21 C22 C23 C24 0.0(4) . .
C22 C23 C24 C25 -1.2(5) . .
C23 C24 C25 C20 0.9(4) . .
C21 C20 C25 C24 0.7(4) . .
C6 C20 C25 C24 176.6(2) . .
