#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:28:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180300 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/14/7151400.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151400
loop_
_publ_author_name
'Christophe Roussel'
'Rachid Fihi'
'Kabula Ciamala'
'Joël Vebrel'
'Touria Zair'
'Claude Riche'
_publ_section_title
;
 Spiroheterocycles from reaction of nitrones with
 methylene-γ-butyrolactones and some of their rearrangements
;
_journal_issue                   15
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              2689
_journal_page_last               2698
_journal_paper_doi               10.1039/b300628j
_journal_volume                  1
_journal_year                    2003
_chemical_compound_source        'chemical synthesis'
_chemical_formula_moiety         'C24 H19 N O5'
_chemical_formula_structural     'C24 H19 N O5'
_chemical_formula_sum            'C24 H19 N O5'
_chemical_formula_weight         401.40
_chemical_name_common            PNOX
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.726(3)
_cell_length_b                   18.482(5)
_cell_length_c                   11.049(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.7
_cell_measurement_theta_min      11.8
_cell_volume                     1936.3(10)
_computing_cell_refinement       'DATCIN Nonius CAD4 software 1987'
_computing_data_collection       'Nonius CAD4 software 1987'
_computing_data_reduction        'NONIUS (Riche, 1989) '
_computing_molecular_graphics    'R3M (Riche,1983) ORTEP(Johnson,1965)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius-CAD4 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7262
_diffrn_reflns_theta_max         67.92
_diffrn_reflns_theta_min         4.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.039
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_restrained_S_obs      1.071
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1188
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2652
_reflns_number_total             3515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300628j.txt
_cod_data_source_block           pnox
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.3547P] 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^)+(0.0576P)^2^+0.3547P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.90843(11) 0.67602(6) 0.84316(10) 0.0477(3) Uani 1 d . .
N2 N 0.77744(13) 0.63649(7) 0.83728(12) 0.0461(3) Uani 1 d . .
C3 C 0.7910(2) 0.57339(9) 0.75830(14) 0.0474(4) Uani 1 d . .
H3 H 0.7432(2) 0.53102(9) 0.78302(14) 0.057 Uiso 1 calc R .
C4 C 0.9490(2) 0.55934(10) 0.7756(2) 0.0570(4) Uani 1 d . .
H4A H 0.9760(2) 0.51460(10) 0.8204(2) 0.068 Uiso 1 calc R .
H4B H 0.9757(2) 0.55691(10) 0.6961(2) 0.068 Uiso 1 calc R .
C5 C 1.0164(2) 0.62437(9) 0.85064(14) 0.0469(4) Uani 1 d . .
C6 C 0.7522(2) 0.62735(9) 0.95900(14) 0.0450(4) Uani 1 d . .
C7 C 0.7743(2) 0.68635(10) 1.0392(2) 0.0560(4) Uani 1 d . .
H7 H 0.8125(2) 0.72883(10) 1.0157(2) 0.067 Uiso 1 calc R .
C8 C 0.7396(2) 0.68200(12) 1.1535(2) 0.0641(5) Uani 1 d . .
H8 H 0.7556(2) 0.72151(12) 1.2069(2) 0.077 Uiso 1 calc R .
C9 C 0.6815(2) 0.61970(12) 1.1894(2) 0.0678(5) Uani 1 d . .
H9 H 0.6583(2) 0.61697(12) 1.2665(2) 0.081 Uiso 1 calc R .
C10 C 0.6583(2) 0.56185(12) 1.1097(2) 0.0669(5) Uani 1 d . .
H10 H 0.6185(2) 0.51980(12) 1.1331(2) 0.080 Uiso 1 calc R .
C11 C 0.6933(2) 0.56511(10) 0.9946(2) 0.0564(4) Uani 1 d . .
H11 H 0.6770(2) 0.52542(10) 0.9416(2) 0.068 Uiso 1 calc R .
C12 C 0.7186(2) 0.59811(9) 0.62671(15) 0.0487(4) Uani 1 d . .
O13 O 0.78897(14) 0.62518(8) 0.56025(12) 0.0680(4) Uani 1 d . .
C14 C 0.5633(2) 0.59189(8) 0.58647(13) 0.0444(4) Uani 1 d . .
C15 C 0.4824(2) 0.54616(9) 0.64272(14) 0.0495(4) Uani 1 d . .
H15 H 0.5259(2) 0.51898(9) 0.71146(14) 0.059 Uiso 1 calc R .
C16 C 0.3388(2) 0.54063(9) 0.5978(2) 0.0543(4) Uani 1 d . .
H16 H 0.2863(2) 0.50937(9) 0.6358(2) 0.065 Uiso 1 calc R .
C17 C 0.2721(2) 0.58137(9) 0.4965(2) 0.0533(4) Uani 1 d . .
C18 C 0.3506(2) 0.62681(10) 0.4382(2) 0.0569(4) Uani 1 d . .
H18 H 0.3069(2) 0.65376(10) 0.3693(2) 0.068 Uiso 1 calc R .
C19 C 0.4943(2) 0.63155(9) 0.48371(15) 0.0531(4) Uani 1 d . .
H19 H 0.5467(2) 0.66215(9) 0.44456(15) 0.064 Uiso 1 calc R .
O20 O 0.12973(14) 0.57281(8) 0.46173(14) 0.0761(4) Uani 1 d . .
C21 C 0.0514(2) 0.61985(14) 0.3688(2) 0.0846(7) Uani 1 d . .
H21A H -0.0469(2) 0.60767(14) 0.3537(2) 0.127 Uiso 1 calc R .
H21B H 0.0841(2) 0.61443(14) 0.2935(2) 0.127 Uiso 1 calc R .
H21C H 0.0645(2) 0.66905(14) 0.3969(2) 0.127 Uiso 1 calc R .
O22 O 1.06782(12) 0.60222(6) 0.98001(10) 0.0526(3) Uani 1 d . .
C23 C 1.2079(2) 0.61748(9) 1.01900(15) 0.0495(4) Uani 1 d . .
C24 C 1.2559(2) 0.65237(9) 0.91703(15) 0.0470(4) Uani 1 d . .
C25 C 1.1420(2) 0.65858(8) 0.81754(14) 0.0460(4) Uani 1 d . .
O26 O 1.27123(15) 0.60205(7) 1.12246(11) 0.0671(4) Uani 1 d . .
C27 C 1.3893(2) 0.67642(10) 0.9112(2) 0.0588(5) Uani 1 d . .
H27 H 1.4655(2) 0.67189(10) 0.9786(2) 0.071 Uiso 1 calc R .
C28 C 1.4043(2) 0.70734(10) 0.8013(2) 0.0648(5) Uani 1 d . .
H28 H 1.4927(2) 0.72292(10) 0.7932(2) 0.078 Uiso 1 calc R .
C29 C 1.2894(2) 0.71549(10) 0.7027(2) 0.0662(5) Uani 1 d . .
H29 H 1.3021(2) 0.73763(10) 0.6304(2) 0.079 Uiso 1 calc R .
C30 C 1.1561(2) 0.69159(10) 0.7089(2) 0.0587(5) Uani 1 d . .
H30 H 1.0793(2) 0.69754(10) 0.6425(2) 0.070 Uiso 1 calc R .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 N2 107.22(11) . . ?
C6 N2 O1 110.40(12) . . ?
C6 N2 C3 121.20(13) . . ?
O1 N2 C3 103.28(12) . . ?
N2 C3 C4 106.22(13) . . ?
N2 C3 C12 103.98(13) . . ?
C4 C3 C12 113.87(15) . . ?
C5 C4 C3 103.48(13) . . ?
O1 C5 O22 109.58(13) . . ?
O1 C5 C25 109.83(13) . . ?
O22 C5 C25 103.75(12) . . ?
O1 C5 C4 106.12(13) . . ?
O22 C5 C4 108.85(13) . . ?
C25 C5 C4 118.55(14) . . ?
C11 C6 C7 119.1(2) . . ?
C11 C6 N2 122.38(14) . . ?
C7 C6 N2 118.2(2) . . ?
C8 C7 C6 120.2(2) . . ?
C9 C8 C7 120.7(2) . . ?
C10 C9 C8 119.0(2) . . ?
C9 C10 C11 121.0(2) . . ?
C6 C11 C10 119.9(2) . . ?
O13 C12 C14 121.6(2) . . ?
O13 C12 C3 119.5(2) . . ?
C14 C12 C3 118.85(14) . . ?
C15 C14 C19 117.8(2) . . ?
C15 C14 C12 123.57(14) . . ?
C19 C14 C12 118.56(15) . . ?
C16 C15 C14 120.83(15) . . ?
C15 C16 C17 120.4(2) . . ?
O20 C17 C16 115.4(2) . . ?
O20 C17 C18 124.7(2) . . ?
C16 C17 C18 119.9(2) . . ?
C19 C18 C17 119.2(2) . . ?
C18 C19 C14 122.0(2) . . ?
C17 O20 C21 118.6(2) . . ?
C23 O22 C5 110.53(13) . . ?
O26 C23 O22 121.0(2) . . ?
O26 C23 C24 130.6(2) . . ?
O22 C23 C24 108.40(13) . . ?
C25 C24 C27 122.0(2) . . ?
C25 C24 C23 108.24(15) . . ?
C27 C24 C23 129.8(2) . . ?
C30 C25 C24 120.8(2) . . ?
C30 C25 C5 130.2(2) . . ?
C24 C25 C5 108.98(14) . . ?
C28 C27 C24 117.2(2) . . ?
C27 C28 C29 120.9(2) . . ?
C28 C29 C30 121.8(2) . . ?
C25 C30 C29 117.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.408(2) . ?
O1 N2 1.458(2) . ?
N2 C6 1.430(2) . ?
N2 C3 1.480(2) . ?
C3 C4 1.528(2) . ?
C3 C12 1.537(2) . ?
C4 C5 1.523(2) . ?
C5 O22 1.464(2) . ?
C5 C25 1.491(2) . ?
C6 C11 1.381(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.380(3) . ?
C8 C9 1.379(3) . ?
C9 C10 1.371(3) . ?
C10 C11 1.389(3) . ?
C12 O13 1.217(2) . ?
C12 C14 1.481(2) . ?
C14 C15 1.391(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.378(2) . ?
C16 C17 1.384(2) . ?
C17 O20 1.361(2) . ?
C17 C18 1.386(3) . ?
C18 C19 1.379(3) . ?
O20 C21 1.429(2) . ?
O22 C23 1.364(2) . ?
C23 O26 1.206(2) . ?
C23 C24 1.462(2) . ?
C24 C25 1.381(2) . ?
C24 C27 1.387(2) . ?
C25 C30 1.381(2) . ?
C27 C28 1.379(3) . ?
C28 C29 1.383(3) . ?
C29 C30 1.386(3) . ?
