#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:00:20 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179608 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/72/4507295.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_4507295
loop_
_publ_author_name
'Yan, Dongpeng'
'Patel, Bhavnita'
'Delori, Amit'
'Jones, William'
'Duan, Xue'
_publ_section_title
;
 The Formation of Hydrogen-Bond Facilitated Salts with Tunable Optical
 Properties: An Experimental and Theoretical Study of
 2,4,5-Triphenylimidazole
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              333
_journal_paper_doi               10.1021/cg3014927
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         '2(C21 H17 N2 1+), C4 F4 O4 2-, 2(H2 O)'
_chemical_formula_sum            'C46 H38 F4 N4 O6'
_chemical_formula_weight         818.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.500(1)
_cell_angle_beta                 109.517(1)
_cell_angle_gamma                94.035(1)
_cell_formula_units_Z            1
_cell_length_a                   8.6090(1)
_cell_length_b                   10.7972(2)
_cell_length_c                   12.1225(2)
_cell_measurement_reflns_used    9590
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     979.96(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19092
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0481
_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)+(0.0443P)²+0.2492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                3813
_reflns_number_total             5723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3014927_si_002.cif
_cod_data_source_block
;
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.19296(15) -0.60058(11) 0.06617(11) 0.0241(2) Uani 1 1 d .
H1A H 0.1632 -0.6878 0.0226 0.029 Uiso 1 1 calc R
N2 N 0.27677(14) -0.38868(11) 0.11806(10) 0.0243(2) Uani 1 1 d .
H2A H 0.3111 -0.3119 0.1144 0.029 Uiso 1 1 calc R
C1 C 0.0211(2) -0.77545(16) 0.35613(15) 0.0355(4) Uani 1 1 d .
H1 H -0.0205 -0.8305 0.3912 0.043 Uiso 1 1 calc R
C2 C -0.0236(2) -0.65239(16) 0.36802(15) 0.0339(3) Uani 1 1 d .
H2 H -0.0946 -0.6225 0.4127 0.041 Uiso 1 1 calc R
C3 C 0.03408(19) -0.57243(15) 0.31548(14) 0.0288(3) Uani 1 1 d .
H3 H 0.0025 -0.4882 0.3239 0.035 Uiso 1 1 calc R
C4 C 0.13871(17) -0.61566(13) 0.25014(13) 0.0239(3) Uani 1 1 d .
C5 C 0.1857(2) -0.73826(15) 0.24084(14) 0.0303(3) Uani 1 1 d .
H5 H 0.2589 -0.7676 0.1982 0.036 Uiso 1 1 calc R
C6 C 0.1267(2) -0.81787(16) 0.29305(15) 0.0358(4) Uani 1 1 d .
H6 H 0.1588 -0.9018 0.2855 0.043 Uiso 1 1 calc R
C7 C 0.19261(17) -0.53688(14) 0.18599(13) 0.0232(3) Uani 1 1 d .
C8 C 0.24704(17) -0.40240(14) 0.21972(13) 0.0236(3) Uani 1 1 d .
C9 C 0.3425(2) -0.07474(16) 0.56580(15) 0.0376(4) Uani 1 1 d .
H9 H 0.3630 -0.0022 0.6431 0.045 Uiso 1 1 calc R
C10 C 0.3800(2) -0.19676(16) 0.56620(14) 0.0352(4) Uani 1 1 d .
H10 H 0.4267 -0.2081 0.6443 0.042 Uiso 1 1 calc R
C11 C 0.35018(19) -0.30284(16) 0.45373(14) 0.0308(3) Uani 1 1 d .
H11 H 0.3777 -0.3861 0.4553 0.037 Uiso 1 1 calc R
C12 C 0.27994(17) -0.28836(14) 0.33795(13) 0.0246(3) Uani 1 1 d .
C13 C 0.2436(2) -0.16462(15) 0.33844(14) 0.0340(4) Uani 1 1 d .
H13 H 0.1972 -0.1524 0.2608 0.041 Uiso 1 1 calc R
C14 C 0.2750(2) -0.05910(17) 0.45180(16) 0.0426(4) Uani 1 1 d .
H14 H 0.2497 0.0249 0.4511 0.051 Uiso 1 1 calc R
C15 C 0.24541(17) -0.50979(14) 0.02644(13) 0.0230(3) Uani 1 1 d .
C16 C 0.26888(17) -0.54059(14) -0.09345(13) 0.0245(3) Uani 1 1 d .
C17 C 0.35198(18) -0.44178(15) -0.11637(14) 0.0276(3) Uani 1 1 d .
H17 H 0.3924 -0.3529 -0.0545 0.033 Uiso 1 1 calc R
C18 C 0.37542(19) -0.47363(16) -0.22947(14) 0.0306(3) Uani 1 1 d .
H18 H 0.4317 -0.4061 -0.2449 0.037 Uiso 1 1 calc R
C19 C 0.3179(2) -0.60244(16) -0.32010(14) 0.0324(3) Uani 1 1 d .
H19 H 0.3342 -0.6235 -0.3975 0.039 Uiso 1 1 calc R
C20 C 0.2367(2) -0.70058(16) -0.29731(15) 0.0377(4) Uani 1 1 d .
H20 H 0.1973 -0.7894 -0.3593 0.045 Uiso 1 1 calc R
C21 C 0.2121(2) -0.67051(15) -0.18474(14) 0.0332(3) Uani 1 1 d .
H21 H 0.1563 -0.7387 -0.1698 0.040 Uiso 1 1 calc R
C22 C 0.36458(18) -0.06766(14) 0.08055(13) 0.0254(3) Uani 1 1 d .
O1 O 0.22204(14) -0.04159(12) 0.04966(12) 0.0419(3) Uani 1 1 d .
O2 O 0.41484(14) -0.15584(10) 0.11889(10) 0.0333(3) Uani 1 1 d .
C23 C 0.49918(18) 0.02309(13) 0.06669(13) 0.0245(3) Uani 1 1 d .
F1 F 0.47197(13) 0.15089(8) 0.09642(9) 0.0415(3) Uani 1 1 d .
F2 F 0.65501(11) 0.03110(10) 0.14768(8) 0.0427(3) Uani 1 1 d .
O1W O -0.06726(15) -0.13396(10) 0.06504(10) 0.0301(2) Uani 1 1 d .
H1W H 0.026(3) -0.1142(19) 0.0605(18) 0.045 Uiso 1 1 d .
H2W H -0.128(2) -0.0745(19) 0.0426(18) 0.045 Uiso 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'
N N 0.0061 0.0033 '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'
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
C15 N1 C7 109.93(11) . .
C15 N1 H1A 125.0 . .
C7 N1 H1A 125.0 . .
C15 N2 C8 109.86(11) . .
C15 N2 H2A 125.1 . .
C8 N2 H2A 125.1 . .
C6 C1 C2 119.69(14) . .
C6 C1 H1 120.2 . .
C2 C1 H1 120.2 . .
C3 C2 C1 120.62(14) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 119.91(14) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 119.04(13) . .
C5 C4 C7 119.88(12) . .
C3 C4 C7 121.01(12) . .
C6 C5 C4 120.67(14) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C1 C6 C5 120.05(15) . .
C1 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C8 C7 N1 106.66(11) . .
C8 C7 C4 133.09(13) . .
N1 C7 C4 120.25(12) . .
C7 C8 N2 106.32(12) . .
C7 C8 C12 130.75(12) . .
N2 C8 C12 122.86(12) . .
C10 C9 C14 119.30(15) . .
C10 C9 H9 120.3 . .
C14 C9 H9 120.3 . .
C9 C10 C11 120.55(14) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C10 C11 C12 120.51(14) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C13 C12 C11 118.56(13) . .
C13 C12 C8 121.70(13) . .
C11 C12 C8 119.73(13) . .
C14 C13 C12 120.29(14) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C9 C14 C13 120.78(15) . .
C9 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
N1 C15 N2 107.20(11) . .
N1 C15 C16 125.35(12) . .
N2 C15 C16 127.41(12) . .
C21 C16 C17 119.21(13) . .
C21 C16 C15 119.96(12) . .
C17 C16 C15 120.81(13) . .
C18 C17 C16 119.87(14) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 120.74(14) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C18 C19 C20 119.51(13) . .
C18 C19 H19 120.2 . .
C20 C19 H19 120.2 . .
C19 C20 C21 120.54(15) . .
C19 C20 H20 119.7 . .
C21 C20 H20 119.7 . .
C20 C21 C16 120.13(14) . .
C20 C21 H21 119.9 . .
C16 C21 H21 119.9 . .
O2 C22 O1 129.82(13) . .
O2 C22 C23 115.38(12) . .
O1 C22 C23 114.79(12) . .
F2 C23 F1 106.34(11) . .
F2 C23 C23 107.91(14) . 2_655
F1 C23 C23 106.92(13) . 2_655
F2 C23 C22 111.10(11) . .
F1 C23 C22 110.19(11) . .
C23 C23 C22 114.01(14) 2_655 .
H1W O1W H2W 105.4(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C15 1.3399(17) .
N1 C7 1.3853(17) .
N1 H1A 0.8800 .
N2 C15 1.3404(17) .
N2 C8 1.3904(17) .
N2 H2A 0.8800 .
C1 C6 1.382(2) .
C1 C2 1.384(2) .
C1 H1 0.9500 .
C2 C3 1.384(2) .
C2 H2 0.9500 .
C3 C4 1.3949(19) .
C3 H3 0.9500 .
C4 C5 1.3908(19) .
C4 C7 1.4734(18) .
C5 C6 1.383(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.3693(19) .
C8 C12 1.4669(19) .
C9 C10 1.379(2) .
C9 C14 1.382(2) .
C9 H9 0.9500 .
C10 C11 1.385(2) .
C10 H10 0.9500 .
C11 C12 1.397(2) .
C11 H11 0.9500 .
C12 C13 1.392(2) .
C13 C14 1.387(2) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.4651(19) .
C16 C21 1.392(2) .
C16 C17 1.3967(19) .
C17 C18 1.385(2) .
C17 H17 0.9500 .
C18 C19 1.381(2) .
C18 H18 0.9500 .
C19 C20 1.382(2) .
C19 H19 0.9500 .
C20 C21 1.385(2) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 O2 1.2364(17) .
C22 O1 1.2399(18) .
C22 C23 1.5528(19) .
C23 F2 1.3484(17) .
C23 F1 1.3633(16) .
C23 C23 1.530(3) 2_655
O1W H1W 0.84(2) .
O1W H2W 0.91(2) .
