#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/43/2014367.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_2014367
loop_
_publ_author_name
'Liu, Hui-Min'
'He, Lei'
'Luo, Xiao-Lan'
'Zhang, Wen-Qin'
_publ_section_title
;
 A zwitterion of 1,5-bis(2-hydroxybenzamido)-3-azapentane: a
 two-dimensional hydrogen-bonding network involving dimers
;
_journal_coeditor_code           JZ1772
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o104
_journal_page_last               o106
_journal_paper_doi               10.1107/S0108270106001545
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H21 N3 O4'
_chemical_formula_moiety         'C18 H21 N3 O4'
_chemical_formula_sum            'C18 H21 N3 O4'
_chemical_formula_weight         343.38
_chemical_melting_point          .423E-305
_chemical_name_systematic
;
2-{N-[2-(2-hydroxybenzamido)ethylammonioethyl]aminocarbonyl}phenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.572(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.775(2)
_cell_length_b                   11.668(2)
_cell_length_c                   14.290(3)
_cell_measurement_reflns_used    2404
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.60
_cell_volume                     1766.1(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9668
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0413
_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)+(0.0557P)²+0.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                2100
_reflns_number_total             3616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1772.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014367
_cod_database_fobs_code          2014367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
O1 0.25783(17) 0.84938(17) 0.16143(12) 0.0922(6) Uani d . 1 . . O
H1 0.163(3) 0.859(2) 0.1689(19) 0.124(10) Uiso d . 1 . . H
O2 0.02119(13) 0.86542(12) 0.13935(10) 0.0640(4) Uani d . 1 . . O
O3 0.05542(12) 0.59885(11) 0.09812(10) 0.0569(4) Uani d . 1 . . O
O4 0.15778(11) 0.26527(11) 0.19007(8) 0.0492(3) Uani d . 1 . . O
N1 -0.10065(14) 0.82938(13) -0.00209(12) 0.0469(4) Uani d . 1 . . N
H1A -0.1077(18) 0.8082(17) -0.0617(15) 0.059(6) Uiso d . 1 . . H
N2 -0.16556(14) 0.66339(13) 0.14445(11) 0.0397(4) Uani d . 1 . . N
H2A -0.1651(19) 0.7140(19) 0.2045(16) 0.078(7) Uiso d . 1 . . H
H2B -0.082(2) 0.6550(16) 0.1283(13) 0.065(6) Uiso d . 1 . . H
N3 -0.01223(13) 0.42939(14) 0.14451(11) 0.0427(4) Uani d . 1 . . N
H3 0.0162(19) 0.3600(16) 0.1635(14) 0.061(6) Uiso d . 1 . . H
C1 0.2439(2) 0.85329(18) 0.06505(16) 0.0624(6) Uani d . 1 . . C
C2 0.3509(2) 0.8554(2) 0.0255(2) 0.0845(8) Uani d . 1 . . C
H2 0.4301 0.8542 0.0647 0.101 Uiso calc R 1 . . H
C3 0.3415(3) 0.8591(2) -0.0718(2) 0.0858(8) Uani d . 1 . . C
H3A 0.4145 0.8604 -0.0979 0.103 Uiso calc R 1 . . H
C4 0.2256(3) 0.86092(19) -0.13090(18) 0.0728(7) Uani d . 1 . . C
H4A 0.2196 0.8634 -0.1966 0.087 Uiso calc R 1 . . H
C5 0.1186(2) 0.85910(16) -0.09136(14) 0.0550(5) Uani d . 1 . . C
H5 0.0400 0.8613 -0.1311 0.066 Uiso calc R 1 . . H
C6 0.12491(17) 0.85403(14) 0.00666(13) 0.0451(5) Uani d . 1 . . C
C7 0.01179(18) 0.84974(14) 0.05174(14) 0.0459(5) Uani d . 1 . . C
C8 -0.21575(17) 0.83078(16) 0.03666(14) 0.0528(5) Uani d . 1 . . C
H8A -0.2829 0.8634 -0.0103 0.063 Uiso calc R 1 . . H
H8B -0.2036 0.8803 0.0921 0.063 Uiso calc R 1 . . H
C9 -0.25665(16) 0.71342(16) 0.06488(13) 0.0465(5) Uani d . 1 . . C
H9A -0.3386 0.7197 0.0834 0.056 Uiso calc R 1 . . H
H9B -0.2653 0.6626 0.0104 0.056 Uiso calc R 1 . . H
C10 -0.19657(17) 0.54503(16) 0.17194(13) 0.0491(5) Uani d . 1 . . C
H10A -0.2876 0.5372 0.1635 0.059 Uiso calc R 1 . . H
H10B -0.1621 0.5335 0.2389 0.059 Uiso calc R 1 . . H
C11 -0.14582(15) 0.45342(15) 0.11464(13) 0.0453(5) Uani d . 1 . . C
H11A -0.1928 0.3833 0.1188 0.054 Uiso calc R 1 . . H
H11B -0.1608 0.4767 0.0484 0.054 Uiso calc R 1 . . H
C12 0.07869(15) 0.50023(16) 0.12951(11) 0.0389(4) Uani d . 1 . . C
C13 0.21071(15) 0.45751(15) 0.15188(11) 0.0399(4) Uani d . 1 . . C
C14 0.30507(17) 0.53558(18) 0.14225(14) 0.0570(5) Uani d . 1 . . C
H14 0.2827 0.6099 0.1226 0.068 Uiso calc R 1 . . H
C15 0.43006(19) 0.5058(2) 0.16096(18) 0.0814(7) Uani d . 1 . . C
H15 0.4919 0.5592 0.1541 0.098 Uiso calc R 1 . . H
C16 0.4628(2) 0.3956(2) 0.19008(18) 0.0827(8) Uani d . 1 . . C
H16 0.5475 0.3747 0.2032 0.099 Uiso calc R 1 . . H
C17 0.37225(19) 0.3160(2) 0.20002(15) 0.0662(6) Uani d . 1 . . C
H17 0.3969 0.2421 0.2195 0.079 Uiso calc R 1 . . H
C18 0.24289(16) 0.34399(17) 0.18141(12) 0.0438(5) Uani d . 1 . . C
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_publ_flag
C1 O1 H1 99.8(15) ?
C7 N1 C8 121.96(17) yes
C7 N1 H1A 121.2(13) ?
C8 N1 H1A 116.6(13) ?
C9 N2 C10 114.78(14) yes
C9 N2 H2A 108.2(11) ?
C10 N2 H2A 106.0(11) ?
C9 N2 H2B 111.7(11) ?
C10 N2 H2B 103.3(11) ?
H2A N2 H2B 112.8(16) ?
C12 N3 C11 123.58(16) yes
C12 N3 H3 113.1(13) ?
C11 N3 H3 122.2(13) ?
O1 C1 C2 118.2(2) ?
O1 C1 C6 121.7(2) ?
C2 C1 C6 120.1(2) ?
C1 C2 C3 120.3(2) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
C4 C3 C2 120.8(2) ?
C4 C3 H3A 119.6 ?
C2 C3 H3A 119.6 ?
C3 C4 C5 119.0(2) ?
C3 C4 H4A 120.5 ?
C5 C4 H4A 120.5 ?
C4 C5 C6 121.7(2) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C5 C6 C1 118.16(19) ?
C5 C6 C7 123.22(18) ?
C1 C6 C7 118.62(18) ?
O2 C7 N1 120.14(18) ?
O2 C7 C6 120.58(17) ?
N1 C7 C6 119.28(17) ?
N1 C8 C9 113.76(15) ?
N1 C8 H8A 108.8 ?
C9 C8 H8A 108.8 ?
N1 C8 H8B 108.8 ?
C9 C8 H8B 108.8 ?
H8A C8 H8B 107.7 ?
N2 C9 C8 112.14(14) ?
N2 C9 H9A 109.2 ?
C8 C9 H9A 109.2 ?
N2 C9 H9B 109.2 ?
C8 C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
N2 C10 C11 113.10(15) ?
N2 C10 H10A 109.0 ?
C11 C10 H10A 109.0 ?
N2 C10 H10B 109.0 ?
C11 C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
N3 C11 C10 114.57(15) ?
N3 C11 H11A 108.6 ?
C10 C11 H11A 108.6 ?
N3 C11 H11B 108.6 ?
C10 C11 H11B 108.6 ?
H11A C11 H11B 107.6 ?
O3 C12 N3 121.85(16) ?
O3 C12 C13 120.64(16) ?
N3 C12 C13 117.50(17) ?
C14 C13 C18 119.97(16) ?
C14 C13 C12 116.58(17) ?
C18 C13 C12 123.45(16) ?
C15 C14 C13 121.7(2) ?
C15 C14 H14 119.1 ?
C13 C14 H14 119.1 ?
C14 C15 C16 118.9(2) ?
C14 C15 H15 120.5 ?
C16 C15 H15 120.5 ?
C17 C16 C15 121.0(2) ?
C17 C16 H16 119.5 ?
C15 C16 H16 119.5 ?
C16 C17 C18 121.4(2) ?
C16 C17 H17 119.3 ?
C18 C17 H17 119.3 ?
O4 C18 C17 120.11(18) ?
O4 C18 C13 122.92(15) ?
C17 C18 C13 116.96(18) ?
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 C1 . 1.359(3) ?
O1 H1 . 1.05(3) ?
O2 C7 . 1.251(2) yes
O3 C12 . 1.244(2) yes
O4 C18 . 1.320(2) ?
N1 C7 . 1.332(2) ?
N1 C8 . 1.448(2) yes
N1 H1A . 0.88(2) ?
N2 C9 . 1.479(2) yes
N2 C10 . 1.490(2) yes
N2 H2A . 1.04(2) ?
N2 H2B . 0.97(2) ?
N3 C12 . 1.329(2) ?
N3 C11 . 1.452(2) yes
N3 H3 . 0.890(19) ?
C1 C2 . 1.375(3) ?
C1 C6 . 1.395(3) ?
C2 C3 . 1.377(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.374(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.480(3) ?
C8 C9 . 1.516(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.509(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.486(2) ?
C13 C14 . 1.391(2) ?
C13 C18 . 1.414(3) ?
C14 C15 . 1.369(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.378(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.372(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.409(3) ?
C17 H17 . 0.9300 ?
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
N1 H1A O4 3_565 0.88(2) 2.01(2) 2.865(2) 165.7(18)
N2 H2A O4 2 1.04(2) 1.61(2) 2.6342(19) 167.0(19)
N2 H2B O3 . 0.97(2) 1.75(2) 2.6933(19) 163.7(17)
N2 H2B O2 . 0.97(2) 2.689(19) 3.109(2) 106.5(13)
N3 H3 O4 . 0.890(19) 1.87(2) 2.6475(19) 145.4(18)
O1 H1 O2 . 1.05(3) 1.51(3) 2.518(2) 158(2)
C5 H5 O4 3_565 0.93 2.60 3.380(3) 141
C11 H11B O3 3_565 0.97 2.71 3.413(2) 130
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
O1 C1 C2 C3 179.9(2)
C6 C1 C2 C3 0.5(4)
C1 C2 C3 C4 0.1(4)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 -0.8(3)
C4 C5 C6 C1 1.4(3)
C4 C5 C6 C7 -178.82(17)
O1 C1 C6 C5 179.47(19)
C2 C1 C6 C5 -1.2(3)
O1 C1 C6 C7 -0.4(3)
C2 C1 C6 C7 178.97(19)
C8 N1 C7 O2 3.5(3)
C8 N1 C7 C6 -176.30(15)
C5 C6 C7 O2 -167.40(17)
C1 C6 C7 O2 12.4(3)
C5 C6 C7 N1 12.3(3)
C1 C6 C7 N1 -167.84(17)
C7 N1 C8 C9 -95.3(2)
C10 N2 C9 C8 -176.63(14)
N1 C8 C9 N2 65.1(2)
C9 N2 C10 C11 86.81(19)
C12 N3 C11 C10 -72.2(2)
N2 C10 C11 N3 78.6(2)
C11 N3 C12 O3 8.4(3)
C11 N3 C12 C13 -171.72(15)
O3 C12 C13 C14 4.4(2)
N3 C12 C13 C14 -175.49(16)
O3 C12 C13 C18 -175.45(16)
N3 C12 C13 C18 4.7(2)
C18 C13 C14 C15 -0.2(3)
C12 C13 C14 C15 179.97(19)
C13 C14 C15 C16 0.0(4)
C14 C15 C16 C17 0.3(4)
C15 C16 C17 C18 -0.3(4)
C16 C17 C18 O4 178.9(2)
C16 C17 C18 C13 0.1(3)
C14 C13 C18 O4 -178.60(16)
C12 C13 C18 O4 1.2(3)
C14 C13 C18 C17 0.1(2)
C12 C13 C18 C17 179.96(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21378941
