#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154077.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_7154077
loop_
_publ_author_name
'Majer, Roberta'
'Konechnaya, Olga'
'Delso, Ignacio'
'Tejero, Tomas'
'Attanasi, Orazio A.'
'Santeusanio, Stefania'
'Merino, Pedro'
_publ_section_title
;
 Highly diastereoselective 1,3-dipolar cycloadditions of chiral
 non-racemic nitrones to 1,2-diaza-1,3-dienes: an experimental and
 computational investigation.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8888
_journal_page_last               8901
_journal_paper_doi               10.1039/c4ob01371a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C18 H24 N4 O5'
_chemical_formula_weight         376.17
_chemical_melting_point          359
_chemical_name_systematic
;
(2S,3S,3aR,4S)-ethyl 4-(benzyloxy)-2-((E)-carbamoyldiazenyl)-2-methylhexahydropyrrolo[1,2-b]isoxazole-3-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0217(7)
_cell_length_b                   13.8727(15)
_cell_length_c                   15.2216(13)
_cell_measurement_reflns_used    728
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.0160
_cell_measurement_theta_min      3.7060
_cell_volume                     1905.1(3)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.1512
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6794
_diffrn_reflns_theta_full        26.26
_diffrn_reflns_theta_max         26.26
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0730
_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/[σ²(Fo²)+(0.0276P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                1917
_reflns_number_total             3148
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ob01371a2.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7154077.cif.
;
_cod_database_code               7154077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.0988(3) 0.0891(2) 0.5867(2) 0.0273(9) Uani 1 1 d .
O2 O 0.2526(3) 0.3632(3) 0.4486(2) 0.0337(9) Uani 1 1 d .
O3 O 0.0226(3) 0.3741(3) 0.3928(2) 0.0286(9) Uani 1 1 d .
O4 O 0.1349(3) 0.4165(2) 0.6534(2) 0.0265(9) Uani 1 1 d .
O5 O -0.3612(3) 0.3119(3) 0.7384(2) 0.0382(10) Uani 1 1 d .
N1 N 0.2005(4) 0.3215(3) 0.6673(3) 0.0255(11) Uani 1 1 d .
N2 N -0.1251(4) 0.3879(3) 0.6553(2) 0.0278(11) Uani 1 1 d .
N3 N -0.2305(4) 0.3599(3) 0.6113(3) 0.0276(11) Uani 1 1 d .
N4 N -0.4820(3) 0.3607(3) 0.6150(2) 0.0277(11) Uani 1 1 d .
H4A H -0.5699 0.3506 0.6348 0.033 Uiso 1 1 calc R
H4B H -0.4698 0.3826 0.5627 0.033 Uiso 1 1 calc R
C1 C 0.1464(5) 0.2796(4) 0.7509(3) 0.0372(14) Uani 1 1 d .
H1A H 0.0478 0.3026 0.7650 0.045 Uiso 1 1 calc R
H1B H 0.2129 0.2943 0.7991 0.045 Uiso 1 1 calc R
C2 C 0.1457(5) 0.1720(4) 0.7304(3) 0.0340(14) Uani 1 1 d .
H2A H 0.2454 0.1459 0.7286 0.041 Uiso 1 1 calc R
H2B H 0.0874 0.1362 0.7729 0.041 Uiso 1 1 calc R
C3 C 0.0742(5) 0.1712(4) 0.6408(3) 0.0238(13) Uani 1 1 d .
H3 H -0.0327 0.1817 0.6471 0.029 Uiso 1 1 calc R
C4 C 0.1437(4) 0.2583(4) 0.5952(3) 0.0238(12) Uani 1 1 d .
H4 H 0.2277 0.2363 0.5596 0.029 Uiso 1 1 calc R
C5 C 0.0433(4) 0.3216(4) 0.5384(3) 0.0191(12) Uani 1 1 d .
H5 H -0.0480 0.2869 0.5236 0.023 Uiso 1 1 calc R
C7 C -0.0174(5) 0.5057(3) 0.5550(3) 0.0340(14) Uani 1 1 d .
H7A H -0.1037 0.5023 0.5183 0.051 Uiso 1 1 calc R
H7B H 0.0673 0.5221 0.5200 0.051 Uiso 1 1 calc R
H7C H -0.0318 0.5540 0.5994 0.051 Uiso 1 1 calc R
C6 C 0.0083(4) 0.4075(4) 0.5990(3) 0.0229(12) Uani 1 1 d .
C8 C 0.1197(5) 0.3543(4) 0.4563(3) 0.0243(12) Uani 1 1 d .
C10 C 0.0436(5) 0.0011(4) 0.6250(4) 0.0364(15) Uani 1 1 d .
H10A H -0.0545 0.0117 0.6492 0.044 Uiso 1 1 calc R
H10B H 0.1085 -0.0196 0.6722 0.044 Uiso 1 1 calc R
C11 C 0.0372(5) -0.0748(4) 0.5554(3) 0.0268(13) Uani 1 1 d .
C12 C 0.1385(6) -0.1487(4) 0.5506(4) 0.0415(15) Uani 1 1 d .
H12 H 0.2125 -0.1536 0.5929 0.050 Uiso 1 1 calc R
C13 C 0.1317(7) -0.2158(4) 0.4836(4) 0.0524(18) Uani 1 1 d .
H13 H 0.2005 -0.2657 0.4815 0.063 Uiso 1 1 calc R
C14 C 0.0236(6) -0.2094(4) 0.4199(4) 0.0450(16) Uani 1 1 d .
H14 H 0.0193 -0.2547 0.3749 0.054 Uiso 1 1 calc R
C15 C -0.0770(5) -0.1361(4) 0.4233(4) 0.0375(15) Uani 1 1 d .
H15 H -0.1501 -0.1313 0.3805 0.045 Uiso 1 1 calc R
C16 C -0.0706(5) -0.0690(4) 0.4900(4) 0.0346(15) Uani 1 1 d .
H16 H -0.1393 -0.0191 0.4915 0.042 Uiso 1 1 calc R
C17 C -0.3656(5) 0.3423(4) 0.6650(3) 0.0261(13) Uani 1 1 d .
C18 C 0.0994(6) 0.5204(4) 0.3174(4) 0.0525(18) Uani 1 1 d .
H18A H 0.1392 0.5448 0.2633 0.079 Uiso 1 1 calc R
H18B H 0.1654 0.5360 0.3648 0.079 Uiso 1 1 calc R
H18C H 0.0043 0.5492 0.3281 0.079 Uiso 1 1 calc R
C09 C 0.0825(5) 0.4131(4) 0.3111(3) 0.0402(16) Uani 1 1 d .
H09A H 0.0167 0.3974 0.2628 0.048 Uiso 1 1 calc R
H09B H 0.1783 0.3841 0.2993 0.048 Uiso 1 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C3 O1 C10 113.0(3)
C8 O3 C09 116.7(3)
C6 O4 N1 109.4(3)
O4 N1 C1 110.2(4)
O4 N1 C4 106.5(3)
C1 N1 C4 106.7(3)
N3 N2 C6 111.5(3)
N2 N3 C17 112.7(4)
N1 C1 C2 102.2(4)
C3 C2 C1 101.2(4)
O1 C3 C2 117.5(4)
O1 C3 C4 107.8(3)
C2 C3 C4 103.2(4)
N1 C4 C3 105.7(4)
N1 C4 C5 106.3(4)
C3 C4 C5 117.9(3)
C8 C5 C4 111.9(3)
C8 C5 C6 111.1(4)
C4 C5 C6 103.1(3)
O4 C6 N2 109.2(4)
O4 C6 C7 107.3(4)
N2 C6 C7 106.8(4)
O4 C6 C5 104.7(4)
N2 C6 C5 111.5(4)
C7 C6 C5 117.1(4)
O2 C8 O3 124.0(4)
O2 C8 C5 124.6(4)
O3 C8 C5 111.4(4)
O1 C10 C11 108.9(4)
C12 C11 C16 118.0(5)
C12 C11 C10 122.4(5)
C16 C11 C10 119.5(5)
C11 C12 C13 120.8(5)
C14 C13 C12 120.5(5)
C15 C14 C13 119.5(6)
C14 C15 C16 120.2(5)
C15 C16 C11 121.1(5)
O5 C17 N4 129.2(5)
O5 C17 N3 123.0(4)
N4 C17 N3 107.7(4)
O3 C09 C18 110.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.422(5)
O1 C10 1.442(5)
O2 C8 1.210(5)
O3 C8 1.334(5)
O3 C09 1.460(5)
O4 C6 1.417(5)
O4 N1 1.460(5)
O5 C17 1.195(5)
N1 C1 1.481(6)
N1 C4 1.496(5)
N2 N3 1.226(4)
N2 C6 1.502(5)
N3 C17 1.488(6)
N4 C17 1.321(5)
C1 C2 1.525(6)
C2 C3 1.510(6)
C3 C4 1.528(6)
C4 C5 1.531(6)
C5 C8 1.497(6)
C5 C6 1.540(6)
C7 C6 1.536(6)
C10 C11 1.495(7)
C11 C12 1.376(6)
C11 C16 1.393(6)
C12 C13 1.381(7)
C13 C14 1.378(7)
C14 C15 1.364(7)
C15 C16 1.379(7)
C18 C09 1.499(6)
