#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:35:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178906 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113582.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_4113582
loop_
_publ_author_name
'Leif Häggman'
'Cecilia Lindblad'
'Hans Oskarsson'
'Ann-Sofi Ullström'
'Ingmar Persson'
_publ_section_title
;
 The Influence of Short Strong Hydrogen Bonding on the Structure and the
 Physicochemical Properties of Alkyl-N-iminodiacetic Acids in Solid State
 and Aqueous Systems
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3631
_journal_page_last               3641
_journal_paper_doi               10.1021/ja021012i
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C16 H31 N O4'
_chemical_formula_weight         301.42
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.3774(17)
_cell_length_b                   9.7376(19)
_cell_length_c                   41.525(8)
_cell_measurement_reflns_used    995
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      19.99
_cell_measurement_theta_min      0.98
_cell_volume                     3387.4(12)
_computing_cell_refinement       'Bruker Saint Plus'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Saint Plus'
_computing_molecular_graphics    'Bruker Shelxtl-NT'
_computing_publication_material  'Bruker Shelxtl-NT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart CCD 1k'
_diffrn_measurement_method       'Bruker Smart'
_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  0.1493
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            9787
_diffrn_reflns_theta_full        19.99
_diffrn_reflns_theta_max         19.99
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9501
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0601
_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)+(0.0601P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                859
_reflns_number_total             1584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021012i_s1_3.cif
_cod_data_source_block           ortnm
_cod_database_code               4113582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
O4 O -0.3872(6) 0.3641(4) 0.21537(10) 0.0629(13) Uani 1 1 d .
N1 N 0.0401(5) 0.3433(4) 0.20042(10) 0.0362(12) Uani 1 1 d .
O3 O -0.2539(4) 0.2096(4) 0.18640(9) 0.0577(11) Uani 1 1 d .
O2 O 0.3409(4) 0.2821(4) 0.20463(10) 0.0744(14) Uani 1 1 d .
C14 C 0.2608(7) 0.1842(7) 0.21481(13) 0.0473(15) Uani 1 1 d .
C10 C 0.0927(6) 0.4700(5) 0.11334(12) 0.0535(16) Uani 1 1 d .
H10A H 0.1841 0.4122 0.1087 0.064 Uiso 1 1 calc R
H10B H -0.0012 0.4236 0.1051 0.064 Uiso 1 1 calc R
C12 C 0.0553(6) 0.3442(5) 0.16423(12) 0.0461(16) Uani 1 1 d .
H12A H 0.1455 0.2871 0.1583 0.055 Uiso 1 1 calc R
H12B H -0.0397 0.3022 0.1552 0.055 Uiso 1 1 calc R
C15 C -0.1163(6) 0.3970(4) 0.21184(11) 0.0383(14) Uani 1 1 d .
H15A H -0.1313 0.4885 0.2031 0.046 Uiso 1 1 calc R
H15B H -0.1124 0.4052 0.2351 0.046 Uiso 1 1 calc R
C16 C -0.2595(8) 0.3103(6) 0.20289(14) 0.0435(15) Uani 1 1 d .
C9 C 0.1122(7) 0.6017(6) 0.09545(13) 0.0703(19) Uani 1 1 d .
H9A H 0.0224 0.6610 0.1004 0.084 Uiso 1 1 calc R
H9B H 0.2082 0.6470 0.1030 0.084 Uiso 1 1 calc R
C13 C 0.0805(6) 0.2050(5) 0.21383(12) 0.0429(14) Uani 1 1 d .
H13A H 0.0322 0.1343 0.2006 0.051 Uiso 1 1 calc R
H13B H 0.0373 0.1968 0.2354 0.051 Uiso 1 1 calc R
O1 O 0.3071(4) 0.0746(4) 0.22554(9) 0.0659(13) Uani 1 1 d .
C8 C 0.1226(7) 0.5852(5) 0.05992(13) 0.0669(18) Uani 1 1 d .
H8A H 0.0298 0.5340 0.0528 0.080 Uiso 1 1 calc R
H8B H 0.2160 0.5300 0.0551 0.080 Uiso 1 1 calc R
C4 C 0.1306(7) 0.8095(6) -0.05036(13) 0.0718(19) Uani 1 1 d .
H4A H 0.0377 0.7541 -0.0554 0.086 Uiso 1 1 calc R
H4B H 0.2240 0.7576 -0.0568 0.086 Uiso 1 1 calc R
C6 C 0.1339(7) 0.6994(5) 0.00471(13) 0.0693(18) Uani 1 1 d .
H6A H 0.2267 0.6451 -0.0011 0.083 Uiso 1 1 calc R
H6B H 0.0403 0.6470 -0.0014 0.083 Uiso 1 1 calc R
C5 C 0.1367(8) 0.8275(5) -0.01496(13) 0.0684(18) Uani 1 1 d .
H5A H 0.0467 0.8840 -0.0086 0.082 Uiso 1 1 calc R
H5B H 0.2331 0.8779 -0.0097 0.082 Uiso 1 1 calc R
C11 C 0.0766(6) 0.4813(5) 0.14915(12) 0.0548(17) Uani 1 1 d .
H11A H 0.1714 0.5247 0.1579 0.066 Uiso 1 1 calc R
H11B H -0.0144 0.5389 0.1543 0.066 Uiso 1 1 calc R
C7 C 0.1323(7) 0.7148(6) 0.04048(13) 0.0693(19) Uani 1 1 d .
H7A H 0.0422 0.7723 0.0462 0.083 Uiso 1 1 calc R
H7B H 0.2284 0.7635 0.0468 0.083 Uiso 1 1 calc R
C2 C 0.1149(8) 0.9164(6) -0.10530(14) 0.081(2) Uani 1 1 d .
H2A H 0.0252 0.8564 -0.1098 0.097 Uiso 1 1 calc R
H2B H 0.2107 0.8683 -0.1120 0.097 Uiso 1 1 calc R
C3 C 0.1238(7) 0.9357(6) -0.07026(14) 0.0653(17) Uani 1 1 d .
H3A H 0.0314 0.9886 -0.0636 0.078 Uiso 1 1 calc R
H3B H 0.2177 0.9904 -0.0655 0.078 Uiso 1 1 calc R
C1 C 0.0981(8) 1.0403(6) -0.12574(13) 0.094(2) Uani 1 1 d .
H1A H 0.0923 1.0134 -0.1480 0.141 Uiso 1 1 calc R
H1B H 0.1887 1.0992 -0.1226 0.141 Uiso 1 1 calc R
H1C H 0.0024 1.0885 -0.1199 0.141 Uiso 1 1 calc R
H16 H 0.120(6) 0.420(6) 0.2099(12) 0.10(2) Uiso 1 1 d .
H22 H -0.483(8) 0.328(6) 0.2098(14) 0.10(3) Uiso 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
C15 N1 C13 113.4(4)
C15 N1 C12 112.9(4)
C13 N1 C12 110.9(4)
O1 C14 O2 128.7(6)
O1 C14 C13 116.2(6)
O2 C14 C13 115.1(6)
C9 C10 C11 116.2(5)
C11 C12 N1 115.8(4)
N1 C15 C16 115.1(4)
O3 C16 O4 126.2(6)
O3 C16 C15 124.5(6)
O4 C16 C15 109.3(5)
C8 C9 C10 114.1(5)
N1 C13 C14 110.7(5)
C9 C8 C7 116.5(5)
C5 C4 C3 117.2(5)
C5 C6 C7 117.4(5)
C4 C5 C6 116.4(5)
C12 C11 C10 111.3(4)
C6 C7 C8 116.8(5)
C3 C2 C1 117.9(5)
C2 C3 C4 116.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C16 1.298(6)
N1 C15 1.488(5)
N1 C13 1.496(5)
N1 C12 1.508(6)
O3 C16 1.197(5)
O2 C14 1.240(6)
C14 O1 1.220(6)
C14 C13 1.524(7)
C10 C9 1.491(6)
C10 C11 1.497(6)
C12 C11 1.485(6)
C15 C16 1.513(7)
C9 C8 1.487(6)
C8 C7 1.500(7)
C4 C5 1.481(6)
C4 C3 1.482(7)
C6 C5 1.491(6)
C6 C7 1.493(6)
C2 C3 1.469(6)
C2 C1 1.482(7)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H16 O1 1.08(6) 1.75(6) 2.792(5) 162(4) 8_665
O4 H22 O2 0.91(7) 1.56(7) 2.455(6) 170(6) 1_455
