#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233122.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_2233122
loop_
_publ_author_name
'Ren, Chang-Yue'
'Hou, Guang-Feng'
'Yu, Ying-Hui'
'Gao, Jin-Sheng'
_publ_section_title
;
 Ethane-1,2-diaminium (R)-2-[4-(1-carboxylatoethoxy)phenoxy]acetate
;
_journal_coeditor_code           CV5213
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o223
_journal_paper_doi               10.1107/S1600536811054535
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C2 H10 N2 2+, C11 H10 O6 2-'
_chemical_formula_moiety         'C2 H10 N2 2+, C11 H10 O6 2-'
_chemical_formula_sum            'C13 H20 N2 O6'
_chemical_formula_weight         300.31
_chemical_name_systematic
;
Ethane-1,2-diaminium (R)-2-[4-(1-carboxylatoethoxy)phenoxy]acetate
;
_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                 99.30(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.066(2)
_cell_length_b                   6.7887(14)
_cell_length_c                   11.050(2)
_cell_measurement_reflns_used    4706
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.99
_cell_volume                     745.2(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0911
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7250
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0662
_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)+(0.0810P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1764
_reflns_number_gt                1855
_reflns_number_total             3288
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5213.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2233122
_cod_database_fobs_code          2233122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
C C1 0.2605(4) 0.7401(6) 0.3560(4) 0.0435(9) Uani d . 1 1
C C2 0.3465(5) 0.8903(5) 0.3366(4) 0.0501(11) Uani d . 1 1
H H2 0.3145 1.0187 0.3261 0.060 Uiso calc R 1 1
C C3 0.4808(4) 0.8504(6) 0.3325(4) 0.0505(11) Uani d . 1 1
H H3 0.5387 0.9525 0.3199 0.061 Uiso calc R 1 1
C C4 0.5296(4) 0.6592(6) 0.3471(4) 0.0481(10) Uani d . 1 1
C C5 0.4409(4) 0.5082(6) 0.3668(4) 0.0508(11) Uani d . 1 1
H H5 0.4718 0.3790 0.3761 0.061 Uiso calc R 1 1
C C6 0.3102(5) 0.5494(6) 0.3723(4) 0.0506(10) Uani d . 1 1
H H6 0.2528 0.4481 0.3872 0.061 Uiso calc R 1 1
C C7 0.0731(4) 0.9589(6) 0.3553(4) 0.0491(10) Uani d . 1 1
H H7 0.1321 1.0400 0.4148 0.059 Uiso calc R 1 1
C C8 0.0612(4) 1.0535(6) 0.2292(4) 0.0462(10) Uani d . 1 1
C C9 -0.0588(6) 0.9415(10) 0.3946(6) 0.0858(17) Uani d . 1 1
H H9A -0.0492 0.8721 0.4712 0.129 Uiso calc R 1 1
H H9B -0.1191 0.8704 0.3337 0.129 Uiso calc R 1 1
H H9C -0.0945 1.0705 0.4045 0.129 Uiso calc R 1 1
C C10 0.7100(5) 0.4428(7) 0.3237(4) 0.0550(11) Uani d . 1 1
H H10A 0.6920 0.3635 0.3922 0.066 Uiso calc R 1 1
H H10B 0.8068 0.4469 0.3267 0.066 Uiso calc R 1 1
C C11 0.6471(4) 0.3445(6) 0.2061(4) 0.0477(10) Uani d . 1 1
C C12 0.2339(4) 0.5461(6) 0.0488(4) 0.0479(10) Uani d . 1 1
H H12A 0.3012 0.5738 0.1200 0.057 Uiso calc R 1 1
H H12B 0.2407 0.6461 -0.0126 0.057 Uiso calc R 1 1
C C13 0.2592(4) 0.3446(6) -0.0019(4) 0.0519(11) Uani d . 1 1
H H13A 0.2658 0.2478 0.0634 0.062 Uiso calc R 1 1
H H13B 0.1838 0.3085 -0.0642 0.062 Uiso calc R 1 1
N N1 0.0972(3) 0.5515(5) 0.0840(3) 0.0455(8) Uani d D 1 1
H H31 0.025(3) 0.541(8) 0.024(3) 0.068 Uiso d D 1 1
H H32 0.086(5) 0.678(3) 0.106(4) 0.068 Uiso d D 1 1
H H33 0.066(4) 0.455(5) 0.128(4) 0.068 Uiso d D 1 1
N N2 0.3835(4) 0.3422(5) -0.0555(3) 0.0475(8) Uani d D 1 1
H H34 0.446(4) 0.367(8) 0.010(3) 0.071 Uiso d D 1 1
H H35 0.392(5) 0.237(5) -0.103(4) 0.071 Uiso d D 1 1
H H36 0.369(5) 0.441(5) -0.111(4) 0.071 Uiso d D 1 1
O O1 0.1245(3) 0.7630(4) 0.3592(3) 0.0525(8) Uani d . 1 1
O O2 0.0518(4) 1.2367(4) 0.2264(3) 0.0759(11) Uani d . 1 1
O O3 0.0581(3) 0.9464(4) 0.1361(3) 0.0542(7) Uani d . 1 1
O O4 0.6629(3) 0.6369(4) 0.3379(3) 0.0578(8) Uani d . 1 1
O O5 0.5970(3) 0.4524(4) 0.1170(3) 0.0576(8) Uani d . 1 1
O O6 0.6516(4) 0.1649(5) 0.2056(3) 0.0761(11) Uani d . 1 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
C2 C1 O1 124.8(4)
C2 C1 C6 119.2(4)
O1 C1 C6 116.0(4)
C1 C2 C3 120.1(4)
C1 C2 H2 120.0
C3 C2 H2 120.0
C2 C3 C4 120.5(4)
C2 C3 H3 119.7
C4 C3 H3 119.7
O4 C4 C3 115.3(4)
O4 C4 C5 126.0(4)
C3 C4 C5 118.8(4)
C6 C5 C4 120.2(4)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 121.2(4)
C5 C6 H6 119.4
C1 C6 H6 119.4
O1 C7 C9 104.9(4)
O1 C7 C8 113.3(4)
C9 C7 C8 111.3(4)
O1 C7 H7 109.0
C9 C7 H7 109.0
C8 C7 H7 109.0
O2 C8 O3 124.5(4)
O2 C8 C7 116.0(4)
O3 C8 C7 119.6(4)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O4 C10 C11 113.9(4)
O4 C10 H10A 108.8
C11 C10 H10A 108.8
O4 C10 H10B 108.8
C11 C10 H10B 108.8
H10A C10 H10B 107.7
O6 C11 O5 125.9(4)
O6 C11 C10 115.8(4)
O5 C11 C10 118.3(4)
N1 C12 C13 109.6(3)
N1 C12 H12A 109.7
C13 C12 H12A 109.7
N1 C12 H12B 109.7
C13 C12 H12B 109.7
H12A C12 H12B 108.2
N2 C13 C12 111.3(3)
N2 C13 H13A 109.4
C12 C13 H13A 109.4
N2 C13 H13B 109.4
C12 C13 H13B 109.4
H13A C13 H13B 108.0
C12 N1 H31 119(3)
C12 N1 H32 105(3)
H31 N1 H32 99(4)
C12 N1 H33 122(3)
H31 N1 H33 91(4)
H32 N1 H33 118(5)
C13 N2 H34 102(3)
C13 N2 H35 114(3)
H34 N2 H35 120(5)
C13 N2 H36 102(3)
H34 N2 H36 115(5)
H35 N2 H36 102(4)
C1 O1 C7 117.4(3)
C4 O4 C10 117.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(6)
C1 O1 1.384(5)
C1 C6 1.389(6)
C2 C3 1.387(6)
C2 H2 0.9300
C3 C4 1.387(6)
C3 H3 0.9300
C4 O4 1.371(5)
C4 C5 1.399(6)
C5 C6 1.356(6)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.426(5)
C7 C9 1.467(6)
C7 C8 1.522(6)
C7 H7 0.9800
C8 O2 1.247(5)
C8 O3 1.256(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O4 1.418(5)
C10 C11 1.507(6)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O6 1.221(5)
C11 O5 1.264(5)
C12 N1 1.489(5)
C12 C13 1.516(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 N2 1.468(6)
C13 H13A 0.9700
C13 H13B 0.9700
N1 H31 0.904(10)
N1 H32 0.907(10)
N1 H33 0.900(10)
N2 H34 0.898(10)
N2 H35 0.900(10)
N2 H36 0.900(10)
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 H33 O2 1_545 0.900(10) 1.858(17) 2.736(5) 164(4)
N1 H32 O3 . 0.907(10) 1.880(12) 2.784(5) 174(5)
N1 H31 O3 2_545 0.904(10) 1.94(3) 2.764(5) 150(5)
N2 H34 O5 . 0.898(10) 1.858(17) 2.736(5) 166(5)
N2 H35 O5 2_645 0.900(10) 1.94(3) 2.748(5) 148(5)
N2 H36 O6 2_655 0.900(10) 1.841(14) 2.736(5) 172(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657311
