Configurationally Stable Longitudinally Twisted Polycyclic Aromatic Compounds
Robert S. Walters; Christina M. Kraml; Neal Byrne; Douglas M. Ho; Qian Qin; Frederick J. Coughlin; Stefan Bernhard; Robert A. Pascal; Journal of the American Chemical Society 130 (2008) 16435–16441; doi:10.1021/ja806958x

data_4108769
_publ_contact_author_address
;
Princeton University
Department of Chemistry
Princeton, NJ   08544-1009
USA
;
_publ_contact_author_email       rpascal@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
;
 Configurationally Stable Longitudinally Twisted Polycyclic Aromatic
 Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16435
_journal_page_last               16441
_journal_paper_doi               10.1021/ja806958x
_journal_volume                  130
_journal_year                    2008
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C57 H37 N . 0.33(C S2)'
_chemical_formula_moiety         '(C57 H37 N), 0.33(C S2)'
_chemical_formula_structural     '(C57 H37 N) 0.33(C S2)'
_chemical_formula_sum            'C57.33 H37 N S0.67'
_chemical_formula_weight         761.27
_chemical_name_systematic
; 
 9,10,11,12,13,14-Hexaphenylbenzo[h]naphtho[2,3-f]quinoline 
 carbon disulfide 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             'December 15, 2007'
_audit_creation_method
;
 SHELXL and manual editing
;
_audit_update_record
;
 Dec. 15, 2007  rap165f.cif       Initial CIF created by RAP.

 Dec. 15, 2007  Sent to CheckCIF  See rap165f_checkcif.pdf for alerts 
                                  that were generated. Comments on these
                                  alerts are given below.

 Aug. 27, 2008  Updates by DMH    Changed "This file (b12sqf.cif)"
                                  to "This file (rap165f.cif)".
                                  Inserted references for completeness.
                                  _chemical_formula_etc
                                  _symmetry_space_group_etc
                                  _exptl_crystal_density_meas
                                  _diffrn_radiation_type
                                  _diffrn_standards_decay_%
                                  _refine_ls_hydrogen_treatment

------------------------------------------------------------------------
                ALERT level A = In general: serious problem
                ALERT level B = Potentially serious problem
                ALERT level C = Check and explain
                ALERT level G = General alerts; check
------------------------------------------------------------------------
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 
            0.550.  Calculated sin(theta_max)/wavelength = 0.5389
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ...... 22.52 Deg. 
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5389
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.8309
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.83

Comment/Explanation: 
            The data were collected to a theta_max of only 22.5 degrees 
            because there is no usable diffraction beyond.  Despite the
            less-than-optimal number of data, the refinement was without
            significant problems and no other level A alerts or any 
            level B alerts were generated.
------------------------------------------------------------------------
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given ... 0.119
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12

Comment/Explanation: 
            The higher value of Rint is not unusual for weak data, where
            the precision of the data is naturally lower.
------------------------------------------------------------------------
PLAT301_ALERT_3_C Main Residue  Disorder ................... 3.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C2 - C3 ........ 1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C6 - C7 ........ 1.38 Ang.

Comment/Explanation: 
            The molecule has two orientations, in which N(4) and C(5)
            are interchanged.  See the _refine_special_details section.
            The slightly short C2-C3 and C6-C7 bonds are due to their
            proximity to these mixed atom sites.
------------------------------------------------------------------------
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .................. 67.00 Perc.

Comment/Explanation: 
            The non-integral number of atoms is due to the partial
            occupancy of the carbon disulfide solvent site.  See the
            _refine_special_details section.
------------------------------------------------------------------------
PLAT230_ALERT_2_C Hirshfeld Test Diff for C33 - C38 ........ 5.14 su   
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) .... 3.12 Ratio

Comment/Explanation:
            A slight "wobble" in the phenyl groups causes some of the
            thermal ellipsoids to be larger than ideal, especially by
            comparison to the very tight ellipsoids of the molecule's
            core.  
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.0110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1255(7)
_cell_length_b                   12.2959(4)
_cell_length_c                   27.6935(15)
_cell_measurement_reflns_used    25411
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.52
_cell_measurement_theta_min      1.62
_cell_volume                     4050.3(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_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
;
 omega scans, 900 0.5 deg frames, 240 sec/deg
;
_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  0.119
_diffrn_reflns_av_sigmaI/netI    0.1180
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25411
_diffrn_reflns_theta_full        22.52
_diffrn_reflns_theta_max         22.52
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       needle
_exptl_crystal_F_000             1595
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.152
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_restrained_S_obs      1.240
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0720
_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^)+(0.0093P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1015
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                3496
_reflns_number_total             5289
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja806958x_si_004.cif
_cod_data_source_block           rap165f
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4108769