Structure/Reactivity Relationships in the Benzo[c]phenanthrene Skeleton: Stable Ion and Electrophilic Substitution (Nitration, Bromination) Study of Substituted Analogues, Novel Carbocations and Substituted Derivatives
Cédric Brulé; Kenneth K. Laali; Takao Okazaki; Mahesh K. Lakshman; Journal of Organic Chemistry 72 (2007) 3232–3241; doi:10.1021/jo0625453

data_4022819
_publ_contact_author_address
;Department of Chemistry
Kent State University
Kent, OH 44242, USA
;
_publ_contact_author_email       klaali@kent.edu
_publ_contact_author_fax         330-672-3816
_publ_contact_author_name        'Kenneth K. Laali'
_publ_contact_author_phone       330-672-2988
_publ_section_title
;
 Structure/Reactivity Relationships in the Benzo[c]phenanthrene
 Skeleton: Stable Ion and Electrophilic Substitution (Nitration,
 Bromination) Study of Substituted Analogues, Novel Carbocations
 and Substituted Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3232
_journal_page_last               3241
_journal_paper_doi               10.1021/jo0625453
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.33
_chemical_name_common
'3,4-dimethoxy-1-nitrobenzo[c]phenanthrene (7aNO2)'
_chemical_name_systematic
;

 3,4-dimethoxy-1-nitrobenzo[c]phenanthrene

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 97.034(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.244(3)
_cell_length_b                   4.5021(14)
_cell_length_c                   33.041(9)
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      2.90
_cell_volume                     1512.3(8)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3806
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0398
_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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1730
_reflns_number_total             2392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0625453si20070228_015723.cif
_cod_data_source_block           laali013_01
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
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
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022819