#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023416.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_4023416
loop_
_publ_author_name
'Saumen Hajra'
'Aswini Kumar Giri'
_publ_contact_author_address
;Department of Chemistry
Indian Institute of Technology
Kharagpur, , 721 302
India
;
_publ_contact_author_email       shajra@chem.iitkgp.ernet.in
_publ_contact_author_fax         (+91)-3222-282252
_publ_contact_author_name        'Dr. Saumen Hajra'
_publ_contact_author_phone       (+91)-3222-283340
_publ_section_title
;
 Organocatalytic and Enantioselective Synthesis of
 β-(Hydroxyalkyl)-γ-Butyrolactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3935
_journal_page_last               3937
_journal_paper_doi               10.1021/jo8005733
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.142(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0650(10)
_cell_length_b                   5.9654(9)
_cell_length_c                   14.695(2)
_cell_measurement_temperature    293(2)
_cell_volume                     531.55(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7909
_diffrn_reflns_theta_full        30.37
_diffrn_reflns_theta_max         30.37
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0444
_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)+(0.0535P)²+0.0766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2150
_reflns_number_total             2797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8005733-File003.cif
_cod_data_source_block           shag_972_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023416
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7354(3) -0.2695(4) 0.84585(13) 0.0425(4) Uani 1 1 d . . .
C2 C 0.5670(3) -0.2390(3) 0.78172(13) 0.0399(4) Uani 1 1 d . . .
H2 H 0.5527 -0.3338 0.7317 0.048 Uiso 1 1 calc R . .
C3 C 0.4204(3) -0.0631(3) 0.79409(13) 0.0406(4) Uani 1 1 d . . .
C4 C 0.4474(4) 0.0723(4) 0.86971(14) 0.0537(6) Uani 1 1 d . . .
H4 H 0.3492 0.1897 0.8786 0.064 Uiso 1 1 calc R . .
C5 C 0.6169(5) 0.0375(5) 0.93259(15) 0.0634(7) Uani 1 1 d . . .
H5 H 0.6308 0.1303 0.9832 0.076 Uiso 1 1 calc R . .
C6 C 0.7645(4) -0.1334(4) 0.92031(14) 0.0536(6) Uani 1 1 d . . .
H6 H 0.8810 -0.1565 0.9614 0.064 Uiso 1 1 calc R . .
C7 C 0.2430(3) -0.0134(3) 0.72299(15) 0.0433(4) Uani 1 1 d . . .
H7 H 0.1027 0.0099 0.7535 0.052 Uiso 1 1 calc R . .
C8 C 0.2989(3) 0.1973(3) 0.66962(13) 0.0387(4) Uani 1 1 d . . .
H8 H 0.3070 0.3251 0.7115 0.046 Uiso 1 1 calc R . .
C9 C 0.5165(3) 0.1793(4) 0.61893(13) 0.0475(5) Uani 1 1 d . . .
H9A H 0.6066 0.3109 0.6306 0.057 Uiso 1 1 calc R . .
H9B H 0.5980 0.0481 0.6393 0.057 Uiso 1 1 calc R . .
C10 C 0.2529(3) 0.2098(3) 0.50651(14) 0.0412(4) Uani 1 1 d . . .
C11 C 0.1345(3) 0.2513(4) 0.59202(15) 0.0500(5) Uani 1 1 d . . .
H11A H 0.0056 0.1556 0.5954 0.060 Uiso 1 1 calc R . .
H11B H 0.0873 0.4064 0.5953 0.060 Uiso 1 1 calc R . .
N1 N 0.8881(3) -0.4570(4) 0.83229(12) 0.0526(5) Uani 1 1 d . . .
O1 O 0.8490(3) -0.5924(3) 0.77155(13) 0.0717(6) Uani 1 1 d . . .
O2 O 1.0498(4) -0.4700(4) 0.88289(14) 0.0868(7) Uani 1 1 d . . .
O3 O 0.2229(3) -0.2024(3) 0.66491(13) 0.0658(5) Uani 1 1 d . . .
H3 H 0.1046 -0.1969 0.6370 0.099 Uiso 1 1 calc R . .
O4 O 0.4642(2) 0.1617(2) 0.52354(9) 0.0464(4) Uani 1 1 d . . .
O5 O 0.1806(3) 0.2168(3) 0.42925(10) 0.0629(5) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.03(19) . . ?
C6 C1 N1 119.22(18) . . ?
C2 C1 N1 117.75(17) . . ?
C1 C2 C3 118.33(18) . . ?
C4 C3 C2 118.75(19) . . ?
C4 C3 C7 120.80(18) . . ?
C2 C3 C7 120.36(18) . . ?
C3 C4 C5 121.6(2) . . ?
C6 C5 C4 120.1(2) . . ?
C1 C6 C5 118.2(2) . . ?
O3 C7 C3 108.13(16) . . ?
O3 C7 C8 111.32(17) . . ?
C3 C7 C8 110.76(16) . . ?
C7 C8 C9 113.27(16) . . ?
C7 C8 C11 114.06(17) . . ?
C9 C8 C11 101.94(16) . . ?
O4 C9 C8 107.70(15) . . ?
O5 C10 O4 120.88(19) . . ?
O5 C10 C11 128.16(19) . . ?
O4 C10 C11 110.96(17) . . ?
C10 C11 C8 106.05(16) . . ?
O2 N1 O1 123.0(2) . . ?
O2 N1 C1 117.8(2) . . ?
O1 N1 C1 119.22(17) . . ?
C10 O4 C9 111.18(15) . . ?
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
C1 C6 1.371(3) . ?
C1 C2 1.388(3) . ?
C1 N1 1.468(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.381(3) . ?
C3 C7 1.514(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.371(4) . ?
C7 O3 1.418(3) . ?
C7 C8 1.523(3) . ?
C8 C9 1.532(3) . ?
C8 C11 1.534(3) . ?
C9 O4 1.435(2) . ?
C10 O5 1.210(2) . ?
C10 O4 1.332(2) . ?
C10 C11 1.481(3) . ?
N1 O2 1.221(3) . ?
N1 O1 1.223(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194744
