#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:24:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178431 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/52/4025201.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_4025201
loop_
_publ_author_name
'Jinling Li'
'Kai Zhang'
'Xiaojie Zhang'
'Kuo-Wei Huang'
'Chunyan Chi'
'Jishan Wu'
_publ_section_title
;
 meso-Substituted Bisanthenes as Soluble and Stable Near-infrared Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              856
_journal_page_last               863
_journal_paper_doi               10.1021/jo902413h
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C42 H20 F6'
_chemical_formula_weight         638.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9112(9)
_cell_length_b                   7.7032(7)
_cell_length_c                   34.108(3)
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.39
_cell_volume                     2866.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0713
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            16887
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0775
_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)+(0.0480P)²+3.3714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1670
_reflns_number_gt                2116
_reflns_number_total             2823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902413h_si_002.cif
_cod_data_source_block           9425pbca
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

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_database_code               4025201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
C1 C 0.0322(3) 0.1859(4) 0.09511(8) 0.0330(7) Uani 1 1 d . . .
C2 C 0.0722(2) 0.2792(4) 0.06201(8) 0.0307(7) Uani 1 1 d . . .
C3 C 0.1236(3) 0.4476(4) 0.06540(9) 0.0357(7) Uani 1 1 d . . .
H3 H 0.1312 0.4988 0.0903 0.043 Uiso 1 1 calc R . .
C4 C 0.1620(3) 0.5357(4) 0.03320(9) 0.0359(7) Uani 1 1 d . . .
H4 H 0.1931 0.6489 0.0359 0.043 Uiso 1 1 calc R . .
C5 C 0.1557(2) 0.4599(4) -0.00394(9) 0.0338(7) Uani 1 1 d . . .
H5 H 0.1859 0.5216 -0.0257 0.041 Uiso 1 1 calc R . .
C6 C 0.1065(2) 0.2968(4) -0.00962(8) 0.0279(7) Uani 1 1 d . . .
C7 C 0.0605(2) 0.2033(4) 0.02382(8) 0.0280(6) Uani 1 1 d . . .
C8 C 0.0057(2) 0.0383(4) 0.01928(7) 0.0260(6) Uani 1 1 d . . .
C9 C -0.0387(2) -0.0517(4) 0.05260(8) 0.0274(6) Uani 1 1 d . . .
C10 C -0.0973(2) -0.2173(4) 0.04860(8) 0.0290(7) Uani 1 1 d . . .
C11 C -0.1429(3) -0.2986(4) 0.08177(9) 0.0387(8) Uani 1 1 d . . .
H11 H -0.1850 -0.4044 0.0792 0.046 Uiso 1 1 calc R . .
C12 C -0.1271(3) -0.2256(4) 0.11907(9) 0.0427(8) Uani 1 1 d . . .
H12 H -0.1574 -0.2847 0.1411 0.051 Uiso 1 1 calc R . .
C13 C -0.0691(3) -0.0714(4) 0.12400(8) 0.0389(8) Uani 1 1 d . . .
H13 H -0.0584 -0.0262 0.1494 0.047 Uiso 1 1 calc R . .
C14 C -0.0243(3) 0.0228(4) 0.09097(8) 0.0330(7) Uani 1 1 d . . .
C15 C 0.0510(3) 0.2597(4) 0.13534(8) 0.0340(7) Uani 1 1 d . . .
C16 C 0.1631(3) 0.2452(5) 0.15402(9) 0.0526(10) Uani 1 1 d . . .
H16 H 0.2294 0.1937 0.1408 0.063 Uiso 1 1 calc R . .
C17 C 0.1790(3) 0.3055(5) 0.19194(9) 0.0531(10) Uani 1 1 d . . .
H17 H 0.2556 0.2946 0.2043 0.064 Uiso 1 1 calc R . .
C18 C 0.0829(3) 0.3811(4) 0.21148(9) 0.0391(8) Uani 1 1 d . A .
C19 C -0.0279(3) 0.4010(4) 0.19289(9) 0.0434(8) Uani 1 1 d . . .
H19 H -0.0934 0.4551 0.2060 0.052 Uiso 1 1 calc R . .
C20 C -0.0432(3) 0.3417(4) 0.15514(9) 0.0404(8) Uani 1 1 d . . .
H20 H -0.1191 0.3572 0.1426 0.049 Uiso 1 1 calc R . .
C21 C 0.0982(4) 0.4337(5) 0.25335(10) 0.0519(9) Uani 1 1 d D . .
F1 F 0.1637(5) 0.5730(5) 0.25829(9) 0.114(2) Uani 0.850(6) 1 d PD A 1
F2 F -0.0084(3) 0.4706(5) 0.27143(7) 0.0884(14) Uani 0.850(6) 1 d PD A 1
F3 F 0.1483(4) 0.3143(4) 0.27539(7) 0.0908(16) Uani 0.850(6) 1 d PD A 1
F1A F 0.0344(18) 0.334(2) 0.2765(5) 0.083(7) Uiso 0.150(6) 1 d PD A 2
F2A F 0.0759(18) 0.5983(14) 0.2551(6) 0.072(6) Uiso 0.150(6) 1 d PD A 2
F3A F 0.2180(9) 0.434(3) 0.2611(5) 0.073(6) Uiso 0.150(6) 1 d PD A 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'
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
C14 C1 C2 120.7(3) . . ?
C14 C1 C15 119.4(3) . . ?
C2 C1 C15 119.9(3) . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 C7 119.6(3) . . ?
C3 C2 C7 118.8(3) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C5 120.6(3) . . ?
C6 C5 C4 121.8(3) . . ?
C5 C6 C7 118.7(3) . . ?
C5 C6 C10 122.3(3) . 5 ?
C7 C6 C10 119.1(3) . 5 ?
C8 C7 C2 120.3(2) . . ?
C8 C7 C6 120.7(2) . . ?
C2 C7 C6 119.1(3) . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 C8 120.2(3) . 5 ?
C9 C8 C8 120.0(3) . 5 ?
C8 C9 C10 120.8(2) . . ?
C8 C9 C14 119.8(3) . . ?
C10 C9 C14 119.4(2) . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 C6 121.8(3) . 5 ?
C9 C10 C6 119.2(2) . 5 ?
C10 C11 C12 121.1(3) . . ?
C13 C12 C11 121.4(3) . . ?
C12 C13 C14 120.5(3) . . ?
C1 C14 C13 121.7(3) . . ?
C1 C14 C9 119.7(3) . . ?
C13 C14 C9 118.6(3) . . ?
C20 C15 C16 118.0(3) . . ?
C20 C15 C1 121.2(3) . . ?
C16 C15 C1 120.8(3) . . ?
C15 C16 C17 120.9(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 C21 119.6(3) . . ?
C19 C18 C21 120.6(3) . . ?
C18 C19 C20 120.1(3) . . ?
C19 C20 C15 121.3(3) . . ?
F2A C21 F1 44.6(8) . . ?
F2A C21 F1A 116.8(13) . . ?
F1 C21 F1A 134.6(9) . . ?
F2A C21 F3 137.8(9) . . ?
F1 C21 F3 106.0(4) . . ?
F1A C21 F3 57.3(10) . . ?
F2A C21 F3A 100.1(12) . . ?
F1 C21 F3A 55.6(9) . . ?
F1A C21 F3A 113.7(13) . . ?
F3 C21 F3A 58.4(9) . . ?
F2A C21 F2 67.0(9) . . ?
F1 C21 F2 103.9(4) . . ?
F1A C21 F2 52.2(10) . . ?
F3 C21 F2 104.3(3) . . ?
F3A C21 F2 139.1(8) . . ?
F2A C21 C18 106.8(9) . . ?
F1 C21 C18 114.1(3) . . ?
F1A C21 C18 111.1(9) . . ?
F3 C21 C18 114.0(3) . . ?
F3A C21 C18 107.4(8) . . ?
F2 C21 C18 113.5(3) . . ?
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
C1 C14 1.407(4) . ?
C1 C2 1.408(4) . ?
C1 C15 1.499(4) . ?
C2 C3 1.418(4) . ?
C2 C7 1.433(4) . ?
C3 C4 1.357(4) . ?
C4 C5 1.397(4) . ?
C5 C6 1.380(4) . ?
C6 C7 1.439(4) . ?
C6 C10 1.467(4) 5 ?
C7 C8 1.414(4) . ?
C8 C9 1.417(4) . ?
C8 C8 1.447(5) 5 ?
C9 C10 1.433(4) . ?
C9 C14 1.438(4) . ?
C10 C11 1.386(4) . ?
C10 C6 1.467(4) 5 ?
C11 C12 1.401(4) . ?
C12 C13 1.356(5) . ?
C13 C14 1.426(4) . ?
C15 C20 1.382(4) . ?
C15 C16 1.384(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.372(5) . ?
C18 C19 1.374(4) . ?
C18 C21 1.494(4) . ?
C19 C20 1.376(4) . ?
C21 F2A 1.293(9) . ?
C21 F1 1.301(4) . ?
C21 F1A 1.305(9) . ?
C21 F3 1.307(4) . ?
C21 F3A 1.335(9) . ?
C21 F2 1.347(4) . ?
