NMR and X-ray structural study of saturated ( p-chlorophenyl)pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared from aroylisobutyric acid and cyclic amino alcohols. High energy barriers for hindered rotation of bridgehead phenyl groups
Tähtinen, Petri; Sillanpää, Reijo; Stájer, Géza; Szabó, Angela E.; Pihlaja, Kalevi; Journal of the Chemical Society, Perkin Transactions 2  (1999) 2011–; doi:10.1039/a905445f

data_7213180
_publ_section_title
;
 NMR and X-ray structural study of saturated
 (&#x200A;p-chlorophenyl)pyrrolo[1,2-a][3,1]benzoxazin-1-ones prepared
 from aroylisobutyric acid and cyclic amino alcohols. High energy barriers
 for hindered rotation of bridgehead phenyl groups
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              2011
_journal_paper_doi               10.1039/a905445f
_journal_year                    1999
_chemical_formula_sum            'C18 H20 Cl N O2'
_chemical_formula_weight         317.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.941(4)
_cell_length_b                   12.749(4)
_cell_length_c                   15.113(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.6
_cell_measurement_theta_min      12.3
_cell_volume                     1663.5(10)
_computing_cell_refinement
;
MSC/AFC5S Control Program (Molecular Structure Corporation, 1995)
;
_computing_data_collection
; 
MSC/AFC5S Control Program (Molecular Structure Corporation, 1995)
;
_computing_data_reduction
;
TEXSAN for WINDOWS(Molecular Structure Corporation, 1997)
;
_computing_molecular_graphics    'ORTEP-3 for WINDOWS (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Rigaku AFC5S'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3121
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0518P)^2^+0.8440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                1631
_reflns_number_total             2925
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            a905445fsup1.cif
_cod_data_source_block           j1404n=6a/6s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.8440P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.8440P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1663.5(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213180