#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229927.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229927
loop_
_publ_author_name
'Flores, Mari Fe'
'Garcia, Pilar'
'M. Garrido, Narciso'
'Sanz, Francisca'
'Diez, David'
_publ_section_title
;
 (3R,4S)-3,4-Isopropylidenedioxy-3,4-dihydro-2H-pyrrole
 1-oxide
;
_journal_coeditor_code           BT5507
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1116
_journal_page_last               o1117
_journal_paper_doi               10.1107/S1600536811013055
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H11 N O3'
_chemical_formula_moiety         'C7 H11 N O3'
_chemical_formula_sum            'C7 H11 N O3'
_chemical_formula_weight         157.17
_chemical_name_systematic
;
(3R,4S)-3,4-Isopropylidenedioxy-3,4-dihydro-2H-pyrrole
1-oxide
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 101.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.335(2)
_cell_length_b                   5.4467(11)
_cell_length_c                   26.508(5)
_cell_measurement_reflns_used    2365
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      66.85
_cell_measurement_theta_min      1.70
_cell_volume                     1604.3(6)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4369
_diffrn_reflns_theta_full        66.85
_diffrn_reflns_theta_max         66.85
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.109
_refine_ls_abs_structure_details 'Flack (1983), 761 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.00105(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2261
_reflns_number_total             2365
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5507.cif
_cod_data_source_block           I
_cod_original_cell_volume        1604.2(6)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2229927
_cod_database_fobs_code          2229927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1' 0.30975(12) 0.5460(3) 0.84350(5) 0.0571(4) Uani d . 1 . .
O O2' 0.44334(11) 0.8279(3) 0.88116(5) 0.0566(4) Uani d . 1 . .
O O3' 0.14788(12) 0.7976(4) 0.96810(6) 0.0693(5) Uani d . 1 . .
N N1' 0.23631(12) 0.7223(3) 0.94785(5) 0.0481(4) Uani d . 1 . .
C C1' 0.33483(16) 0.4762(4) 0.89604(7) 0.0476(4) Uani d . 1 . .
H H1' 0.3729 0.3142 0.9013 0.057 Uiso calc R 1 . .
C C3' 0.34095(15) 0.8196(4) 0.95186(6) 0.0464(4) Uani d . 1 . .
H H3' 0.3657 0.9601 0.9709 0.056 Uiso calc R 1 . .
C C4' 0.41764(14) 0.6811(4) 0.92243(6) 0.0463(4) Uani d . 1 . .
H H4' 0.4907 0.6168 0.9445 0.056 Uiso calc R 1 . .
C C5' 0.40764(17) 0.6940(4) 0.83486(7) 0.0525(5) Uani d . 1 . .
C C6' 0.3627(3) 0.8714(6) 0.79227(9) 0.0866(8) Uani d . 1 . .
H H6'1 0.2985 0.9674 0.8009 0.130 Uiso calc R 1 . .
H H6'2 0.3337 0.7826 0.7610 0.130 Uiso calc R 1 . .
H H6'3 0.4271 0.9780 0.7876 0.130 Uiso calc R 1 . .
C C7' 0.5109(3) 0.5377(6) 0.82529(12) 0.0928(9) Uani d . 1 . .
H H7'1 0.4860 0.4458 0.7941 0.139 Uiso calc R 1 . .
H H7'2 0.5349 0.4266 0.8536 0.139 Uiso calc R 1 . .
H H7'3 0.5776 0.6413 0.8221 0.139 Uiso calc R 1 . .
C C2' 0.22244(16) 0.4919(4) 0.91839(8) 0.0553(5) Uani d . 1 . .
H H2'1 0.1510 0.4965 0.8913 0.066 Uiso calc R 1 . .
H H2'2 0.2168 0.3528 0.9406 0.066 Uiso calc R 1 . .
O O1 0.09613(11) 0.3663(3) 0.62016(5) 0.0557(4) Uani d . 1 . .
O O2 0.21761(13) 0.6589(3) 0.66182(5) 0.0666(5) Uani d . 1 . .
O O3 0.36792(14) 0.3733(4) 0.52993(7) 0.0861(6) Uani d . 1 . .
N N1 0.29356(13) 0.4731(4) 0.55436(6) 0.0544(4) Uani d . 1 . .
C C1 0.10961(15) 0.5348(4) 0.58059(7) 0.0514(5) Uani d . 1 . .
H H1 0.0341 0.6186 0.5659 0.062 Uiso calc R 1 . .
C C2 0.16439(16) 0.4088(4) 0.54033(7) 0.0556(5) Uani d . 1 . .
H H2A 0.1530 0.2325 0.5413 0.067 Uiso calc R 1 . .
H H2B 0.1293 0.4687 0.5062 0.067 Uiso calc R 1 . .
C C3 0.31507(17) 0.6385(4) 0.58935(8) 0.0586(5) Uani d . 1 . .
H H3 0.3910 0.7049 0.6014 0.070 Uiso calc R 1 . .
C C4 0.20620(17) 0.7127(4) 0.60855(7) 0.0522(5) Uani d . 1 . .
H H4 0.1847 0.8848 0.6007 0.063 Uiso calc R 1 . .
C C5 0.12362(18) 0.4967(4) 0.66756(7) 0.0558(5) Uani d . 1 . .
C C6 0.0151(3) 0.6365(7) 0.67681(11) 0.0971(10) Uani d . 1 . .
H H6A -0.0464 0.5228 0.6816 0.146 Uiso calc R 1 . .
H H6B -0.0148 0.7394 0.6477 0.146 Uiso calc R 1 . .
H H6C 0.0374 0.7365 0.7070 0.146 Uiso calc R 1 . .
C C7 0.1714(3) 0.3142(6) 0.70956(9) 0.0882(8) Uani d . 1 . .
H H7A 0.2404 0.2320 0.7016 0.132 Uiso calc R 1 . .
H H7B 0.1101 0.1958 0.7120 0.132 Uiso calc R 1 . .
H H7C 0.1942 0.3990 0.7418 0.132 Uiso calc R 1 . .
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'
H H 0.0000 0.0000 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1' O1' C5' . . 107.35(14) ?
C5' O2' C4' . . 107.96(15) ?
C3' N1' O3' . . 127.85(19) ?
C3' N1' C2' . . 113.34(15) ?
O3' N1' C2' . . 118.74(16) ?
O1' C1' C2' . . 110.46(15) ?
O1' C1' C4' . . 103.80(15) ?
C2' C1' C4' . . 105.50(15) ?
O1' C1' H1' . . 112.2 ?
C2' C1' H1' . . 112.2 ?
C4' C1' H1' . . 112.2 ?
N1' C3' C4' . . 111.98(18) ?
N1' C3' H3' . . 124.0 ?
C4' C3' H3' . . 124.0 ?
O2' C4' C3' . . 110.31(17) ?
O2' C4' C1' . . 104.86(13) ?
C3' C4' C1' . . 103.90(14) ?
O2' C4' H4' . . 112.4 ?
C3' C4' H4' . . 112.4 ?
C1' C4' H4' . . 112.4 ?
O2' C5' O1' . . 104.48(13) ?
O2' C5' C6' . . 108.5(2) ?
O1' C5' C6' . . 109.05(19) ?
O2' C5' C7' . . 109.8(2) ?
O1' C5' C7' . . 111.2(2) ?
C6' C5' C7' . . 113.4(2) ?
C5' C6' H6'1 . . 109.5 ?
C5' C6' H6'2 . . 109.5 ?
H6'1 C6' H6'2 . . 109.5 ?
C5' C6' H6'3 . . 109.5 ?
H6'1 C6' H6'3 . . 109.5 ?
H6'2 C6' H6'3 . . 109.5 ?
C5' C7' H7'1 . . 109.5 ?
C5' C7' H7'2 . . 109.5 ?
H7'1 C7' H7'2 . . 109.5 ?
C5' C7' H7'3 . . 109.5 ?
H7'1 C7' H7'3 . . 109.5 ?
H7'2 C7' H7'3 . . 109.5 ?
N1' C2' C1' . . 104.30(16) ?
N1' C2' H2'1 . . 110.9 ?
C1' C2' H2'1 . . 110.9 ?
N1' C2' H2'2 . . 110.9 ?
C1' C2' H2'2 . . 110.9 ?
H2'1 C2' H2'2 . . 108.9 ?
C5 O1 C1 . . 106.97(16) ?
C5 O2 C4 . . 108.22(15) ?
O3 N1 C3 . . 127.89(18) ?
O3 N1 C2 . . 119.33(19) ?
C3 N1 C2 . . 112.67(16) ?
O1 C1 C2 . . 110.37(18) ?
O1 C1 C4 . . 102.75(14) ?
C2 C1 C4 . . 105.98(15) ?
O1 C1 H1 . . 112.4 ?
C2 C1 H1 . . 112.4 ?
C4 C1 H1 . . 112.4 ?
N1 C2 C1 . . 103.94(16) ?
N1 C2 H2A . . 111.0 ?
C1 C2 H2A . . 111.0 ?
N1 C2 H2B . . 111.0 ?
C1 C2 H2B . . 111.0 ?
H2A C2 H2B . . 109.0 ?
N1 C3 C4 . . 112.86(17) ?
N1 C3 H3 . . 123.6 ?
C4 C3 H3 . . 123.6 ?
O2 C4 C3 . . 111.49(17) ?
O2 C4 C1 . . 105.37(15) ?
C3 C4 C1 . . 102.97(17) ?
O2 C4 H4 . . 112.2 ?
C3 C4 H4 . . 112.2 ?
C1 C4 H4 . . 112.2 ?
O2 C5 O1 . . 104.75(13) ?
O2 C5 C6 . . 111.0(2) ?
O1 C5 C6 . . 110.64(19) ?
O2 C5 C7 . . 108.8(2) ?
O1 C5 C7 . . 107.8(2) ?
C6 C5 C7 . . 113.4(2) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1' C1' . 1.417(2) ?
O1' C5' . 1.426(2) ?
O2' C5' . 1.416(2) ?
O2' C4' . 1.431(2) ?
O3' N1' . 1.2937(19) ?
N1' C3' . 1.284(2) ?
N1' C2' . 1.470(3) ?
C1' C2' . 1.510(2) ?
C1' C4' . 1.535(3) ?
C1' H1' . 0.9800 ?
C3' C4' . 1.484(3) ?
C3' H3' . 0.9300 ?
C4' H4' . 0.9800 ?
C5' C6' . 1.497(3) ?
C5' C7' . 1.509(4) ?
C6' H6'1 . 0.9600 ?
C6' H6'2 . 0.9600 ?
C6' H6'3 . 0.9600 ?
C7' H7'1 . 0.9600 ?
C7' H7'2 . 0.9600 ?
C7' H7'3 . 0.9600 ?
C2' H2'1 . 0.9700 ?
C2' H2'2 . 0.9700 ?
O1 C5 . 1.423(2) ?
O1 C1 . 1.425(2) ?
O2 C5 . 1.415(2) ?
O2 C4 . 1.423(2) ?
O3 N1 . 1.281(2) ?
N1 C3 . 1.282(3) ?
N1 C2 . 1.480(2) ?
C1 C2 . 1.502(3) ?
C1 C4 . 1.538(3) ?
C1 H1 . 0.9800 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.481(3) ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9800 ?
C5 C6 . 1.507(3) ?
C5 C7 . 1.511(4) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O1 3 0.93 2.44 3.366(3) 171
C1 H1 O3 3_455 0.98 2.38 3.355(3) 171
C2 H2A O3 4_546 0.97 2.70 3.441(3) 134
C2 H2B O3 4_556 0.97 2.41 3.120(3) 130
C2' H2'1 O2' 3_445 0.97 2.49 3.247(2) 135
C4' H4' O3' 3_545 0.98 2.48 3.375(3) 152
C2' H2'2 O3' 4_547 0.97 2.61 3.254(2) 124
C3' H3' O3' 4_557 0.93 2.48 3.345(3) 156
