#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152805.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_7152805
loop_
_publ_author_name
'Ganesh Kumar, Mothukuri'
'Mali, Sachitanand M.'
'Gopi, Hosahudya N.'
_publ_section_title
;
 Synthesis and stereochemical analysis of β-nitromethane substituted
 γ-amino acids and peptides.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              803
_journal_page_last               813
_journal_paper_doi               10.1039/c2ob27070f
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C16 H30 N2 O6'
_chemical_formula_sum            'C16 H30 N2 O6'
_chemical_formula_weight         346.42
_chemical_name_systematic        Boc-gL(b-CH2NO2)-COOEt
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   11.306(6)
_cell_length_b                   31.857(16)
_cell_length_c                   5.353(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1928.0(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10883
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'graphite monochromator'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin rod'
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method EtOAc
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0931
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1258P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2320
_refine_ls_wR_factor_ref         0.2660
_reflns_number_gt                2600
_reflns_number_total             4625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27070f.txt
_cod_data_source_block           2c
_cod_original_cell_volume        1928.2(17)
_cod_database_code               7152805
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_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 0.2206(4) 0.22852(9) 0.5784(5) 0.0433(10) Uani 1 1 d .
O2 O 0.2092(3) 0.17427(9) 0.3052(5) 0.0374(8) Uani 1 1 d .
O3 O -0.1488(4) 0.13189(11) 0.9800(7) 0.0574(11) Uani 1 1 d .
O4 O -0.1998(4) 0.09223(12) 0.6737(8) 0.0633(12) Uani 1 1 d .
O5 O 0.1006(3) 0.05249(9) 1.2682(6) 0.0393(9) Uani 1 1 d .
O6 O 0.1635(4) -0.00050(9) 1.0287(6) 0.0540(12) Uani 1 1 d .
N1 N 0.2125(4) 0.16449(10) 0.7273(6) 0.0372(10) Uani 1 1 d .
H1 H 0.2159 0.1771 0.8693 0.045 Uiso 1 1 calc R
N2 N -0.1290(5) 0.11553(12) 0.7796(9) 0.0490(12) Uani 1 1 d .
C1 C 0.2231(5) 0.26122(13) 0.3831(8) 0.0400(13) Uani 1 1 d .
C2 C 0.3342(4) 0.25696(15) 0.2261(10) 0.0406(12) Uani 1 1 d .
H2A H 0.4021 0.2558 0.3336 0.061 Uiso 1 1 calc R
H2B H 0.3409 0.2807 0.1167 0.061 Uiso 1 1 calc R
H2C H 0.3298 0.2317 0.1288 0.061 Uiso 1 1 calc R
C3 C 0.2296(8) 0.30101(15) 0.5422(11) 0.077(2) Uani 1 1 d .
H3A H 0.1649 0.3013 0.6582 0.115 Uiso 1 1 calc R
H3B H 0.2250 0.3252 0.4359 0.115 Uiso 1 1 calc R
H3C H 0.3030 0.3014 0.6323 0.115 Uiso 1 1 calc R
C4 C 0.1125(5) 0.26054(16) 0.2277(10) 0.0478(14) Uani 1 1 d .
H4A H 0.1077 0.2344 0.1391 0.072 Uiso 1 1 calc R
H4B H 0.1144 0.2833 0.1103 0.072 Uiso 1 1 calc R
H4C H 0.0448 0.2635 0.3344 0.072 Uiso 1 1 calc R
C5 C 0.2127(5) 0.18803(12) 0.5178(8) 0.0325(11) Uani 1 1 d .
C6 C 0.2067(5) 0.11887(12) 0.7250(8) 0.0384(12) Uani 1 1 d .
H6 H 0.2151 0.1095 0.5515 0.046 Uiso 1 1 calc R
C7 C 0.3093(6) 0.10069(17) 0.8736(10) 0.0588(18) Uani 1 1 d .
H7A H 0.3091 0.0704 0.8531 0.071 Uiso 1 1 calc R
H7B H 0.2963 0.1066 1.0492 0.071 Uiso 1 1 calc R
C8 C 0.4367(8) 0.1181(4) 0.7971(15) 0.156(6) Uani 1 1 d D
H8 H 0.4587 0.1450 0.8729 0.188 Uiso 1 1 calc R
C9 C 0.4751(11) 0.1123(4) 0.546(2) 0.163(6) Uani 1 1 d D
H9A H 0.5595 0.1091 0.5427 0.245 Uiso 1 1 calc R
H9B H 0.4530 0.1363 0.4480 0.245 Uiso 1 1 calc R
H9C H 0.4386 0.0876 0.4779 0.245 Uiso 1 1 calc R
C10 C 0.5096(13) 0.0780(5) 0.896(3) 0.206(6) Uani 1 1 d U
H10A H 0.5417 0.0629 0.7566 0.309 Uiso 1 1 calc R
H10B H 0.4577 0.0599 0.9889 0.309 Uiso 1 1 calc R
H10C H 0.5729 0.0873 1.0025 0.309 Uiso 1 1 calc R
C11 C 0.0855(5) 0.10437(13) 0.8191(8) 0.0401(13) Uani 1 1 d .
H11 H 0.0756 0.1149 0.9897 0.048 Uiso 1 1 calc R
C12 C -0.0118(5) 0.12284(15) 0.6610(9) 0.0401(12) Uani 1 1 d .
H12A H 0.0011 0.1528 0.6411 0.048 Uiso 1 1 calc R
H12B H -0.0106 0.1101 0.4966 0.048 Uiso 1 1 calc R
C13 C 0.0735(6) 0.05646(13) 0.8272(8) 0.0500(15) Uani 1 1 d .
H13A H -0.0090 0.0491 0.8021 0.060 Uiso 1 1 calc R
H13B H 0.1183 0.0446 0.6898 0.060 Uiso 1 1 calc R
C14 C 0.1152(5) 0.03694(13) 1.0661(8) 0.0385(13) Uani 1 1 d .
C15 C 0.1986(5) -0.02382(13) 1.2530(9) 0.0453(14) Uani 1 1 d .
H15A H 0.2049 -0.0535 1.2141 0.054 Uiso 1 1 calc R
H15B H 0.1389 -0.0204 1.3817 0.054 Uiso 1 1 calc R
C16 C 0.3151(6) -0.00787(16) 1.3464(12) 0.0611(18) Uani 1 1 d .
H16A H 0.3737 -0.0109 1.2179 0.092 Uiso 1 1 calc R
H16B H 0.3386 -0.0237 1.4907 0.092 Uiso 1 1 calc R
H16C H 0.3078 0.0212 1.3905 0.092 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
C5 O1 C1 120.8(3)
C14 O6 C15 116.3(3)
C5 N1 C6 123.3(4)
O3 N2 O4 123.2(5)
O3 N2 C12 118.3(5)
O4 N2 C12 118.5(4)
O1 C1 C4 111.4(4)
O1 C1 C2 110.2(4)
C4 C1 C2 112.4(4)
O1 C1 C3 101.0(4)
C4 C1 C3 111.1(5)
C2 C1 C3 110.1(5)
O2 C5 O1 125.2(4)
O2 C5 N1 125.1(4)
O1 C5 N1 109.6(3)
N1 C6 C7 110.0(5)
N1 C6 C11 109.8(4)
C7 C6 C11 113.3(4)
C6 C7 C8 114.9(4)
C9 C8 C7 118.1(11)
C9 C8 C10 93.0(9)
C7 C8 C10 95.8(9)
C12 C11 C6 110.6(4)
C12 C11 C13 109.8(4)
C6 C11 C13 112.9(4)
N2 C12 C11 110.5(4)
C14 C13 C11 114.2(4)
O5 C14 O6 124.3(4)
O5 C14 C13 123.7(4)
O6 C14 C13 112.0(4)
O6 C15 C16 109.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.333(5)
O1 C1 1.476(5)
O2 C5 1.220(5)
O3 N2 1.213(5)
O4 N2 1.230(6)
O5 C14 1.201(5)
O6 C14 1.327(6)
O6 C15 1.467(5)
N1 C5 1.349(5)
N1 C6 1.455(5)
N2 C12 1.488(7)
C1 C4 1.502(8)
C1 C2 1.516(7)
C1 C3 1.529(6)
C6 C7 1.521(7)
C6 C11 1.531(7)
C7 C8 1.597(13)
C8 C9 1.425(12)
C8 C10 1.610(14)
C11 C12 1.508(7)
C11 C13 1.533(6)
C13 C14 1.498(6)
C15 C16 1.498(8)
