Transformation of Zwitterionic Pyridine Derivatives to a Spiro-Fused Ring System: Azoniabenzo[de]fluorine. Synthesis and Mechanistic Rationalization.
Palkó, Roberta; Egyed, Orsolya; Rokob, Tibor András; Bombicz, Petra; Riedl, Zsuzsanna; Hajós, György; The Journal of organic chemistry 80 (2014) 174–; doi:10.1021/jo5022663

data_4030299
_publ_section_title
;
 Transformation of Zwitterionic Pyridine Derivatives to a Spiro-Fused Ring
 System: Azoniabenzo[de]fluorine. Synthesis and Mechanistic
 Rationalization.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              174
_journal_paper_doi               10.1021/jo5022663
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C27 H23 N2 O, C2 H3 N, Br'
_chemical_formula_sum            'C29 H26 Br N3 O'
_chemical_formula_weight         512.44
_chemical_melting_point          485
_chemical_name_systematic
;
6-methyl-10-oxo-11,11-diphenyl-4,4a,10,11-tetrahydro-
9H-9-aza-11b-azoniabenzo[de]fluorene bromide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                91.2659(9)
_cell_angle_beta                 104.1456(14)
_cell_angle_gamma                104.6546(14)
_cell_formula_units_Z            2
_cell_length_a                   8.9351(3)
_cell_length_b                   10.5522(3)
_cell_length_c                   14.2075(4)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      35.8736
_cell_measurement_theta_min      2.4389
_cell_volume                     1251.64(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
RAXIS conversion
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            59698
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.173
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  0.6603
_exptl_absorpt_correction_T_min  0.4344
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 NUMABS Higashi, T. (1998), rev. 2002. (Rigaku/MSC Inc.).
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       Prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0409P)^2^+0.5850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5082
_reflns_number_total             5714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5022663_si_001.cif
_cod_data_source_block           PR592
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030299.cif.
;
_cod_database_code               4030299
_shelx_estimated_absorpt_t_min   0.730
_shelx_estimated_absorpt_t_max   0.850
_shelxl_version_number           2013-4
_shelx_res_checksum              57404
_shelx_hkl_checksum              98515