Synthesis, Structure, and Resolution of Exceptionally Twisted Pentacenes
Jun Lu; Douglas M. Ho; Nancy J. Vogelaar; Christina M. Kraml; Stefan Bernhard; Neal Byrne; Laura R. Kim; Robert A. Pascal; Journal of the American Chemical Society 128 (2006) 17043–17050; doi:10.1021/ja065935f

data_4111263
_publ_contact_author_address
;
Princeton University
Department of Chemistry
Princeton, NJ   08544-1009
USA
;
_publ_contact_author_email       snake@princeton.edu
_publ_contact_author_fax         '(609) 258 6746'
_publ_contact_author_name        'Professor Robert A. Pascal, Jr.'
_publ_contact_author_phone       '(609) 258 5417'
_publ_section_title
;
 Synthesis, Structure, and Resolution of Exceptionally Twisted Pentacenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17043
_journal_page_last               17050
_journal_paper_doi               10.1021/ja065935f
_journal_volume                  128
_journal_year                    2006
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac
;
C74 H46 O2 . 3.25(C H2 Cl2) . 0.75(C2 H6 S O)
;
_chemical_formula_moiety
;
C74 H46 O2, 3.25(C H2 Cl2), 0.75(C2 H6 S O)
;
_chemical_formula_structural
;
C74 H46 O2 . 3.25(C H2 Cl2) . 0.75(C2 H6 S O)
;
_chemical_formula_sum            'C78.75 H57 Cl6.5 O2.75 S0.75'
_chemical_formula_weight         1301.71
_chemical_name_systematic
;
9,10,11,20,21,22-Hexaphenyltetrabenzo[a,c,l,n]pentacene (9,22),(11,20)-
Diepoxide Dichloromethane Dimethylsulfoxide Solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             'July 21, 2006'
_audit_creation_method
;
SHELXL and manual editing of form.cif
;
_audit_update_record
;
July 21, 2006  rap129f.cif        Initial CIF created by DMH.

July 21, 2006  Sent to Checkcif.  See rap129f_checkcif.pdf for
                                  the alerts that were generated.
                                  Selected responses follow.

-------------------------------------------------------------------------
ABSTM02_ALERT_3_C The expected to reported ratio Tmax/Tmin(RR') is < 0.90
                  Tmin and Tmax reported:                     0.755 0.923
                  Tmin(prime) and Tmax expected:              0.909 0.932
                  RR(prime) =                                       0.838
                  Please check that your absorption correction.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............... 0.84

                  ABSTM02_ALERT_3_C and PLAT061_ALERT_3_C indicate that
                  some reflections are overly corrected.  This is likely
                  due to not having a representive number of reflections
                  to fully describe the absorption surface.  numerical
                  and analytical absorption corrections were not appli-
                  cable to the sample, so our choice was to go with the
                  psi-scan correction nevertheless.  In spite of some
                  overly corrected reflections, the corrected data gave
                  significantly improved refinement results versus the
                  uncorrected data.  Therefore, while not perfect, it is
                  that best that we have and so we choose to retain and
                  use it rather than using the uncorrected data.
                  

PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ ............ ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ......... ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)........ ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ....... ?
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
                  _chemical_formula_sum (cfm) and the formula from the
                  _atom_site* data (asd).
                  cfm .......... C78.75  H57        Cl6.5   O2.75  S0.75
                  asd .......... C78.78  H57.07999  Cl6.52  O2.76
CELLZ01_ALERT_1_G Difference between formula and atom_site contents
                  detected.
CELLZ01_ALERT_1_G Check formula stoichiometry or atom site occupancies.
                  From the CIF: _cell_formula_units_Z 2
                  From the CIF: _chemical_formula_sum C78.75 H57 Cl6.50
                                O2.75 S0.75
                  Compare cell contents of formula and atom_site data
                                atom  Z*formula  cif sites  diff
                                C      157.50     157.56   -0.06
                                H      114.00     114.16   -0.16
                                Cl      13.00      13.04   -0.04
                                O        5.50       5.52   -0.02
                                S        1.50       1.52   -0.02

                  PLAT041_ALERT_1_C, PLAT042_ALERT_1_C, PLAT068_ALERT_
                  1_C, PLAT077_ALERT_4_C, FORMU01_ALERT_2_G, CELLZ01_
                  ALERT_1_G and CELLZ01_ALERT_1_G are all related to
                  chemical formula for the compound.  These appear to be
                  false alerts due to roundoff and other bugs in the
                  validation softwares "Calc" routine.  Therefore, we
                  choose to retain the "Reported" values in our CIF.
                  Regarding the non-integer number of atoms, "Valid
                  reasons include partially occupied (solvent) sites and
                  substitutional disorder".  That is indeed the case,
                  i.e., partial dichloromethane and dimethylsulfoxide
                  solvent molecules are present.

PLAT244_ALERT_4_C Low  Solvent  Ueq as Compared to Neighbors for .... C39
PLAT244_ALERT_4_C Low  Solvent  Ueq as Compared to Neighbors for ..... S1
PLAT244_ALERT_4_C Low  Solvent  Ueq as Compared to Neighbors for ... C39*
PLAT302_ALERT_4_C Anion/Solvent Disorder .................... 26.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3

                  PLAT244_ALERT_4_C, PLAT302_ALERT_4_C and PLAT720_ALERT
                  _4_C are all with respect to the compositional disorder
                  in one of the two solvent sites in the asymmetric unit.
                  C39, C39* and S1 are the central atoms in partial
                  dichloromethane and dimethylsulfoxide molecules.  It is
                  not at all unusual for such atoms to show significantly
                  lower Ueq values versus the terminal chlorines, oxygen
                  or methyl moieties attached to them.  The partial
                  dichloromethanes are labelled [C(39),Cl(3),Cl(4)] and
                  [C(39*),Cl(3*),Cl(4*)] where the latter "starred" atoms
                  correspond to the minor component of the disorder.  It
                  is the latter "starred" atoms that CheckCif considers
                  "Unusual/Non-Standard".  We do not believe them to be
                  overly unusual, and so we choose to retain them as is.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 126.091(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6834(2)
_cell_length_b                   18.7000(3)
_cell_length_c                   16.3911(2)
_cell_measurement_reflns_used    42871
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.88
_cell_volume                     3141.53(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO-SMN (Otwinowski & Minor, 1997), Siemens SHELXTL (Sheldrick, 1996)
;
_computing_molecular_graphics    'Siemens SHELXTL (Sheldrick, 1996)'
_computing_publication_material  'Siemens SHELXTL (Sheldrick, 1996)'
_computing_structure_refinement  'Siemens SHELXTL (Sheldrick, 1996)'
_computing_structure_solution    'Siemens SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       '\w scans, 800 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42871
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.92341
_exptl_absorpt_correction_T_min  0.75507
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Siemens SHELXTL (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0045(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.032
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7211
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.030
_refine_ls_restrained_S_gt       1.047
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1164P)^2^+2.8308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2231
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                5328
_reflns_number_total             7211
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja065935fsi20060815_063503.cif
_cod_data_source_block           rap129f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C78.75 H57 Cl6.50 O2.75 S0.75'
_cod_database_code               4111263