Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl - experimental and DFT computational study.
Kadina, Anastasia P.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; Pérez, Pedro J; Yufit, Dmitry S.; Organic & biomolecular chemistry 10 (2012) 5582–5591; doi:10.1039/c2ob25676b

data_7152428
_publ_section_title
;
 Intramolecular cycloaddition of azomethine ylides, from imines of
 O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl -
 experimental and DFT computational study.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5582
_journal_page_last               5591
_journal_paper_doi               10.1039/c2ob25676b
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C25 H22 Br N O5'
_chemical_formula_sum            'C25 H22 Br N O5'
_chemical_formula_weight         496.35
_chemical_melting_point          404.1(5)
_chemical_name_systematic
;
ethyl (2RS,3RS,5RS)-4-(4-bromophenyl)-2-(4-methoxyphenyl)-2,3,4,5-tetrohydro-2,5-
epoxy-1,4-benzoxazepine-3-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                65.4650(10)
_cell_angle_beta                 89.4570(10)
_cell_angle_gamma                70.3560(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1931(2)
_cell_length_b                   11.5561(3)
_cell_length_c                   13.5965(4)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.075
_cell_measurement_theta_min      2.671
_cell_volume                     1090.13(5)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12682
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.67
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0534 before and 0.0202 after correction.
The Ratio of minimum to maximum transmission is 0.1749.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                5629
_reflns_number_total             6586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25676b.txt
_cod_data_source_block           exo_2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '130.5-131.5 C' was changed to
'404.1(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' 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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152428