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_4108768
_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          'C58 H37 N O . 2(C H2 Cl2)'
_chemical_formula_moiety         'C58 H37 N O, 2(C H2 Cl2)'
_chemical_formula_structural     '(C58 H37 N O) 2(C H2 Cl2)'
_chemical_formula_sum            'C60 H41 Cl4 N O'
_chemical_formula_weight         933.74
_chemical_name_systematic
;
9,10,11,12,13,14-Hexaphenyl-15-oxo-9,14-dihydro-9,14-
methanobenzo[h]naphtho[2,3-f]quinoline Bis(dichloromethane) Solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             'May 15, 2007'
_audit_creation_method
;
SHELXL and manual editing of form.cif
;
_audit_update_record
;
May 15, 2007  rap164f.cif         Initial CIF created by DMH.

May 15, 2007  README sections     See _exptl_special_details for a brief
                                  discussion of the data collection and
                                  data reduction procedures and results.
                                  (Located about a third of the way from
                                  the begin of this file.)

                                  See _refine_special_details for a
                                  brief discussion of the structure
                                  solution and refinement, disorder
                                  treatment, etc.  (Located about a
                                  third-to-halfway from the begin of
                                  this file.)

May 15, 2007  Sent to Checkcif.   See rap164f_checkcif.pdf for
                                  the alerts that were generated.
                                  Selected responses follow.

Aug 27, 2008  Updates by DMH      Section 3. TITLE AND AUTHOR LIST
                                  _chemical_formula_structural

------------------------------------------------------------------------

PLAT415_ALERT_2_B Short Inter D-H..H-X  H5 .. H22 ............ 2.08 Ang.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ..... 3.01 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ..................... 3.00 Perc.
PLAT243_ALERT_4_C High Solvent Ueq as Compared to Neighbors for ... Cl2S
PLAT243_ALERT_4_C High Solvent Ueq as Compared to Neighbors for ... Cl2T
PLAT244_ALERT_4_C Low  Solvent Ueq as Compared to Neighbors for .... C1S
PLAT302_ALERT_4_C Anion/Solvent Disorder ................... 14.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ............ 6
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......... 18

                  PLAT220_ALERT_2_C to PLAT860_ALERT_3_G result from the
                  presence of disorder.  The disorder was treated as well
                  as might be expected (see _refine_special_details).
                  The H5...H22 short contact is consistent with the
                  disordering of the N4 and C5 positions, and partially
                  alleviated by the H5 atom being only half-occupied.
                  The validation software finds the labels for the 6
                  dichloromethane H atoms (H1SA, H1SB), (H1SC, H1SD) and
                  (H2SA, H2SB) to be unusual.  The first two sets are
                  the partial hydrogens on C1S due to disorder.  The
                  second set are the two fully occupied hydrogens on
                  C2S.  The use of restraints is not an uncommon
                  practice in the treatment of disorder.  Since there is
                  some logic to the choice of labels, and the use of
                  minimal and mild restraints is accepted practice, we
                  will elect to retain the model as is.

PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ....... 5

                  The C-C standard uncertainties and bond precisions
                  range from 0.004 to 0.006 with the average bond
                  precision being 0.005.  No response to this alert is
                  necessary since these standard uncertainty values are
                  quite typical of CCD-based structure determinations.

PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C2 - C3 .......... 1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C6 - C7 .......... 1.39 Ang.

                  The bond distances for the 12 C(sp2)-C(sp2) aromatic
                  bonds of the two terminal six-membered rings of the
                  benzoquinoline moiety range from 1.349(4) to 1.451(4)
                  Angstroms.  Five of twelve C-C bonds are longer than
                  C2-C3 and C6-C7.  Six of twelve C-C bonds are shorter
                  than C2-C3 and C6-C7.  Hence, the C2-C3 and C6-C7
                  bonds are not short at all, and no response to
                  PLAT366_ALERT_2_C is necessary.

PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ........... S
PLAT793_ALERT_1_G Check the Absolute Configuration of C14 = .......... R

                  The CheckCif (9S,14R) assignment for the coordinates
                  in this cif file are consistent with our own manual
                  assignment.  However, it is fully recognized that the
                  compound crystallizes in the centric space group P-1,
                  and that equal amounts of the (9S,14R) and (9R,14S)
                  enantiomers are required by crystallographic inversion
                  symmetry to be present in the unit cell and crystal,
                  i.e., the compound is racemic.
;
_cell_angle_alpha                62.804(2)
_cell_angle_beta                 80.102(4)
_cell_angle_gamma                84.972(3)
_cell_formula_units_Z            2
_cell_length_a                   12.8717(7)
_cell_length_b                   14.1496(10)
_cell_length_c                   14.7329(10)
_cell_measurement_reflns_used    21292
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.57
_cell_volume                     2351.0(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       '\w scans, 600 1.0\% 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  0.062
_diffrn_reflns_av_sigmaI/netI    0.089
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       Needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.134
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         8202
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.135
_refine_ls_restrained_S_obs      1.190
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          -0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+1.8570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1691
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                5996
_reflns_number_total             8202
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja806958x_si_003.cif
_cod_data_source_block           rap164f
_cod_database_code               4108768