#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/19/2221967.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_2221967
loop_
_publ_author_name
'Tao, Yuan'
'Liang, Yu-Feng'
'Guo, Xiao-Qiang'
'Mao, Zhi-Hua'
'Qi, Qing-Rong'
_publ_section_title
;
 3,3'-[(tert-Butoxycarbonyl)azanediyl]dipropanoic acid
;
_journal_coeditor_code           CI2799
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1408
_journal_paper_doi               10.1107/S1600536809018911
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H19 N O6'
_chemical_formula_moiety         'C11 H19 N O6'
_chemical_formula_sum            'C11 H19 N O6'
_chemical_formula_weight         261.27
_chemical_name_systematic
;
3,3'-[(tert-Butoxycarbonyl)azanediyl]dipropanoic acid
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.632(2)
_cell_length_b                   14.559(3)
_cell_length_c                   18.257(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      6.79
_cell_measurement_theta_min      5.69
_cell_volume                     2826.0(10)
_computing_cell_refinement       'DIFRAC (Gabe & White, 1993)'
_computing_data_collection       'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2-θ
_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  0.0081
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2979
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        1.251
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.248
_refine_ls_extinction_coef       0.0127(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.0538
_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)+(0.0701P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1705
_reflns_number_gt                1050
_reflns_number_total             2601
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2799.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2826.1(11)
_cod_database_code               2221967
_cod_database_fobs_code          2221967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
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 0.1690(2) 0.18631(13) 0.36711(10) 0.0709(7) Uani d . 1 . .
O O2 0.0153(3) 0.10681(16) 0.31021(11) 0.0841(8) Uani d . 1 . .
O O3 0.0720(3) -0.04162(19) 0.08342(15) 0.0995(10) Uani d . 1 . .
H H3O 0.031(4) -0.058(3) 0.037(3) 0.129(16) Uiso d . 1 . .
O O4 0.0484(3) 0.09467(16) 0.03663(14) 0.1078(11) Uani d . 1 . .
O O5 0.1228(3) 0.49187(18) 0.26626(13) 0.0833(8) Uani d . 1 . .
H H5O 0.066(5) 0.526(3) 0.238(2) 0.137(18) Uiso d . 1 . .
O O6 0.1031(3) 0.39281(16) 0.17583(15) 0.1142(11) Uani d . 1 . .
N N1 0.1433(3) 0.20065(16) 0.24663(13) 0.0669(8) Uani d . 1 . .
C C1 0.2392(4) 0.1974(2) 0.48679(17) 0.0898(12) Uani d . 1 . .
H H1A 0.3223 0.1849 0.4687 0.135 Uiso calc R 1 . .
H H1B 0.2328 0.1772 0.5367 0.135 Uiso calc R 1 . .
H H1C 0.2233 0.2622 0.4843 0.135 Uiso calc R 1 . .
C C2 0.1697(4) 0.0451(2) 0.4391(2) 0.0981(14) Uani d . 1 . .
H H2A 0.1055 0.0146 0.4112 0.147 Uiso calc R 1 . .
H H2B 0.1700 0.0217 0.4882 0.147 Uiso calc R 1 . .
H H2C 0.2501 0.0342 0.4169 0.147 Uiso calc R 1 . .
C C3 0.0128(4) 0.1701(3) 0.4649(2) 0.1067(14) Uani d . 1 . .
H H3A -0.0026 0.2343 0.4571 0.160 Uiso calc R 1 . .
H H3B 0.0038 0.1560 0.5160 0.160 Uiso calc R 1 . .
H H3C -0.0467 0.1347 0.4371 0.160 Uiso calc R 1 . .
C C4 0.1436(4) 0.1469(2) 0.44047(16) 0.0686(10) Uani d . 1 . .
C C5 0.1046(4) 0.1604(2) 0.30812(18) 0.0623(9) Uani d . 1 . .
C C6 0.0904(4) 0.1711(2) 0.17744(16) 0.0688(10) Uani d . 1 . .
H H6A 0.1042 0.2185 0.1409 0.083 Uiso calc R 1 . .
H H6B 0.0003 0.1629 0.1829 0.083 Uiso calc R 1 . .
C C7 0.1484(3) 0.0821(2) 0.15127(17) 0.0747(11) Uani d . 1 . .
H H7A 0.2365 0.0922 0.1400 0.090 Uiso calc R 1 . .
H H7B 0.1437 0.0368 0.1902 0.090 Uiso calc R 1 . .
C C8 0.0838(4) 0.0459(3) 0.08533(19) 0.0719(10) Uani d . 1 . .
C C9 0.2554(4) 0.2605(2) 0.24626(18) 0.0762(10) Uani d . 1 . .
H H9A 0.2844 0.2675 0.1962 0.091 Uiso calc R 1 . .
H H9B 0.3220 0.2308 0.2738 0.091 Uiso calc R 1 . .
C C10 0.2318(4) 0.3548(2) 0.27853(18) 0.0762(11) Uani d . 1 . .
H H10A 0.1970 0.3475 0.3273 0.091 Uiso calc R 1 . .
H H10B 0.3116 0.3865 0.2833 0.091 Uiso calc R 1 . .
C C11 0.1451(4) 0.4125(2) 0.2344(2) 0.0732(11) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C4 . . 121.8(3) ?
C8 O3 H3O . . 108(2) ?
C11 O5 H5O . . 110(3) ?
C5 N1 C6 . . 119.0(3) ?
C5 N1 C9 . . 120.9(3) ?
C6 N1 C9 . . 119.0(3) ?
C4 C1 H1A . . 109.5 ?
C4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C2 H2A . . 109.5 ?
C4 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C4 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C4 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O1 C4 C3 . . 110.5(3) ?
O1 C4 C2 . . 109.4(3) ?
C3 C4 C2 . . 113.4(3) ?
O1 C4 C1 . . 101.2(3) ?
C3 C4 C1 . . 110.4(3) ?
C2 C4 C1 . . 111.3(3) ?
O2 C5 O1 . . 123.5(3) ?
O2 C5 N1 . . 123.0(3) ?
O1 C5 N1 . . 113.5(3) ?
N1 C6 C7 . . 111.8(3) ?
N1 C6 H6A . . 109.3 ?
C7 C6 H6A . . 109.3 ?
N1 C6 H6B . . 109.3 ?
C7 C6 H6B . . 109.3 ?
H6A C6 H6B . . 107.9 ?
C8 C7 C6 . . 111.8(3) ?
C8 C7 H7A . . 109.2 ?
C6 C7 H7A . . 109.2 ?
C8 C7 H7B . . 109.2 ?
C6 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
O4 C8 O3 . . 122.6(3) ?
O4 C8 C7 . . 122.5(4) ?
O3 C8 C7 . . 114.9(3) ?
N1 C9 C10 . . 113.5(3) ?
N1 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
N1 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C11 C10 C9 . . 113.9(3) ?
C11 C10 H10A . . 108.8 ?
C9 C10 H10A . . 108.8 ?
C11 C10 H10B . . 108.8 ?
C9 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
O6 C11 O5 . . 122.7(3) ?
O6 C11 C10 . . 125.6(3) ?
O5 C11 C10 . . 111.6(3) ?
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 C5 . 1.331(4) ?
O1 C4 . 1.482(3) ?
O2 C5 . 1.229(4) ?
O3 C8 . 1.281(4) ?
O3 H3O . 0.98(5) ?
O4 C8 . 1.199(4) ?
O5 C11 . 1.315(4) ?
O5 H5O . 0.94(5) ?
O6 C11 . 1.193(4) ?
N1 C5 . 1.331(4) ?
N1 C6 . 1.448(4) ?
N1 C9 . 1.477(4) ?
C1 C4 . 1.514(5) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C2 C4 . 1.508(4) ?
C2 H2A . 0.96 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C3 C4 . 1.499(5) ?
C3 H3A . 0.96 ?
C3 H3B . 0.96 ?
C3 H3C . 0.96 ?
C6 C7 . 1.513(4) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.482(5) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C9 C10 . 1.515(4) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C11 . 1.486(5) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
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
O3 H3O O4 5 0.98(5) 1.68(5) 2.653(4) 174(4)
O5 H5O O2 7_566 0.94(5) 1.70(5) 2.628(3) 168(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 C4 C3 . . . . -63.2(4) ?
C5 O1 C4 C2 . . . . 62.3(4) ?
C5 O1 C4 C1 . . . . 179.9(3) ?
C4 O1 C5 O2 . . . . 4.4(5) ?
C4 O1 C5 N1 . . . . -177.7(3) ?
C6 N1 C5 O2 . . . . -8.8(5) ?
C9 N1 C5 O2 . . . . -176.5(3) ?
C6 N1 C5 O1 . . . . 173.3(3) ?
C9 N1 C5 O1 . . . . 5.6(4) ?
C5 N1 C6 C7 . . . . -78.3(4) ?
C9 N1 C6 C7 . . . . 89.6(3) ?
N1 C6 C7 C8 . . . . 173.1(3) ?
C6 C7 C8 O4 . . . . 39.8(5) ?
C6 C7 C8 O3 . . . . -142.1(3) ?
C5 N1 C9 C10 . . . . -76.4(4) ?
C6 N1 C9 C10 . . . . 115.9(3) ?
N1 C9 C10 C11 . . . . -67.1(4) ?
C9 C10 C11 O6 . . . . -5.7(6) ?
C9 C10 C11 O5 . . . . 177.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14522867
