Stereoselective Cycloaddition of Dibenzoxazepinium Ylides to Acetylenes and Fullerene C60. Conformational Behavior of 3-Aryldibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine Systems
Alexander F. Khlebnikov; Mikhail S. Novikov; Petr P. Petrovskii; Alexander S. Konev; Dmitrii S. Yufit; Stanislav I. Selivanov; Holm Frauendorf; Journal of Organic Chemistry 75 (2010) 5211–5215; doi:10.1021/jo100966j

data_4025570
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email       d.s.yufit@durham.ac.uk
_publ_contact_author_fax         '0191 384 4737'
_publ_contact_author_name        'Dmitry Yufit'
_publ_contact_author_phone       '0191 334 2004'
_publ_section_title
;
 Stereoselective Cycloaddition of Dibenzoxazepinium Ylides to Acetylenes
 and Fullerene C60. Conformational Behavior of
 3-Aryldibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5211
_journal_page_last               5215
_journal_paper_doi               10.1021/jo100966j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_chemical_melting_point          204
_chemical_name_systematic
;
Methyl (3RS,13bRS)-3-phenyl-3,13b-dihydrodibenzo[b,f]pyrrolo[1,2-d]
[1,4]oxazepine-2-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.75(2)
_cell_angle_beta                 113.51(2)
_cell_angle_gamma                94.86(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2576(2)
_cell_length_b                   11.0167(2)
_cell_length_c                   11.0998(2)
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.373
_cell_measurement_theta_min      2.16
_cell_volume                     888.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_publication_material
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11429
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.4033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0435 before and 0.0249 after correction.
 The Ratio of minimum to maximum transmission is 0.4033.
 The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0600P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                3363
_reflns_number_total             4242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100966j_si_006.cif
_cod_data_source_block           SAD_15A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025570