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_4108767
_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          'C60 H37 N . 2(C2 H4 Cl2)'
_chemical_formula_moiety         'C60 H37 N, 2(C2 H4 Cl2)'
_chemical_formula_structural     '(C60 H37 N) 2(C2 H4 Cl2)'
_chemical_formula_sum            'C64 H45 Cl4 N'
_chemical_formula_weight         969.81
_chemical_name_systematic
; 
 9,10,19,21-Tetraphenyldiphenanthro[9,10-b:9,10-h]carbazole 
 Bis(1,2-dichloroethane) Solvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'July 8, 2008'
_audit_creation_method
;
 SHELXL and manual editing
;
_audit_update_record
;
 July 8, 2008   carbf.cif         Initial CIF created by RAP.

 July 8, 2008   Sent to CheckCIF  See carbf_checkcif.pdf for alerts 
                                  that were generated. Comments on these
                                  alerts are given below.

 Aug 27, 2008   Updates by DMH    Bis(1,2-dichloroethane) above and in
                                      _chemical_name_systematic
                                  _chemical_formula_etc
                                  _symmetry_space_group_etc
                                  _exptl_crystal_density_meas
                                  _exptl_special_details
                                  _refine_ls_hydrogen_treatment
                                  H31 coordinates
                                  PLAT066_ALERT_1_C

------------------------------------------------------------------------
                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
------------------------------------------------------------------------
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
 
Comment/Explanation: This N-H group is too sterically encumbered to 
            form a hydrogen bond!
------------------------------------------------------------------------
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?

Comment/Explanation: 0.9186 and 0.9801 are not identical.
------------------------------------------------------------------------
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?

Comment/Explanation: 4859.73(17) and 4859.7(2) are not inconsistent!
------------------------------------------------------------------------
PLAT231_ALERT_4_C Hirshfeld Test (Solvent) Cl2 -- C1T .. 6.79 su
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for Cl3
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
PLAT302_ALERT_4_G Anion/Solvent Disorder .................. 38.00 Perc.

Comment/Explanation: The solvent disorder model is not perfect, but
             these minor problems, and the few restraints, are surely
             acceptable for a situation in which there is a large 
             disordered solvent region.
------------------------------------------------------------------------
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels .......... 10

Comment/Explanation: All of the labels are clear; it is not obvious
             which labels CheckCIF considers unusual.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7735(3)
_cell_length_b                   21.8039(4)
_cell_length_c                   16.3499(3)
_cell_measurement_reflns_used    7426
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.25
_cell_volume                     4859.73(17)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
_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      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1387 0.5\% rotations'
_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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28919
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.017
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5576
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.030
_refine_ls_restrained_S_obs      1.053
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0444P)^2^+7.4143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1268
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                4170
_reflns_number_total             5578
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja806958x_si_002.cif
_cod_data_source_block           carbf
_cod_original_cell_volume        4859.7(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4108767