#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/01/2210170.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_2210170
loop_
_publ_author_name
'Xing-You Xu'
'Tong-Tao Xu'
'Da-Qi Wang'
'Jian Gao'
'Guo-Xiang Xu'
_publ_section_title
;
 2-[1-(2-Hydroxyethyliminio)ethyl]-5-methoxyphenolate
;
_journal_coeditor_code           CI2143
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4030
_journal_page_last               o4031
_journal_paper_doi               10.1107/S1600536806033393
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C11 H15 N O3'
_chemical_formula_sum            'C11 H15 N O3'
_chemical_formula_weight         209.24
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   6.2552(5)
_cell_length_b                   6.3403(5)
_cell_length_c                   26.648(2)
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      3.058
_cell_volume                     1056.86(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX area-dectector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5346
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1088P)²+0.0099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1061
_reflns_number_total             1133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ci2143.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        1056.86(15)
_cod_database_code               2210170
_cod_database_fobs_code          2210170
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'
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
C C1 0.3704(4) 0.9880(4) 0.87938(7) 0.0401(5) Uani d . 1
C C2 0.2575(4) 0.7950(4) 0.87015(7) 0.0384(5) Uani d . 1
C C3 0.3345(4) 0.6605(4) 0.83177(8) 0.0464(6) Uani d . 1
H H3 0.2629 0.5346 0.8256 0.056 Uiso calc R 1
C C4 0.5088(4) 0.7083(4) 0.80358(8) 0.0497(6) Uani d . 1
H H4 0.5544 0.6173 0.7784 0.060 Uiso calc R 1
C C5 0.6193(4) 0.8969(4) 0.81298(8) 0.0427(6) Uani d . 1
C C6 0.5525(4) 1.0333(4) 0.84943(8) 0.0436(5) Uani d . 1
H H6 0.6275 1.1580 0.8547 0.052 Uiso calc R 1
C C7 0.0706(4) 0.7411(4) 0.89851(8) 0.0383(5) Uani d . 1
C C8 -0.0532(4) 0.5432(4) 0.88822(9) 0.0513(6) Uani d . 1
H H8A -0.1724 0.5346 0.9108 0.077 Uiso calc R 1
H H8B 0.0380 0.4230 0.8930 0.077 Uiso calc R 1
H H8C -0.1044 0.5452 0.8543 0.077 Uiso calc R 1
C C9 -0.1834(4) 0.8454(4) 0.96514(9) 0.0475(6) Uani d . 1
H H9A -0.1690 0.7225 0.9866 0.057 Uiso calc R 1
H H9B -0.3083 0.8259 0.9441 0.057 Uiso calc R 1
C C10 -0.2107(4) 1.0399(4) 0.99685(8) 0.0475(6) Uani d . 1
H H10A -0.2038 1.1647 0.9759 0.057 Uiso calc R 1
H H10B -0.3491 1.0372 1.0133 0.057 Uiso calc R 1
C C11 0.9172(5) 1.1128(5) 0.79080(11) 0.0627(8) Uani d . 1
H H11A 1.0346 1.1142 0.7676 0.094 Uiso calc R 1
H H11B 0.9712 1.1154 0.8245 0.094 Uiso calc R 1
H H11C 0.8288 1.2344 0.7852 0.094 Uiso calc R 1
N N1 0.0066(3) 0.8679(3) 0.93390(7) 0.0416(5) Uani d . 1
H H1 0.0850 0.9768 0.9395 0.050 Uiso calc R 1
O O1 0.3106(3) 1.1180(3) 0.91390(7) 0.0569(5) Uani d . 1
O O2 -0.0469(3) 1.0458(3) 1.03307(7) 0.0596(5) Uani d . 1
H H2A -0.0689 1.1434 1.0526 0.089 Uiso calc R 1
O O3 0.7942(3) 0.9268(3) 0.78345(6) 0.0558(5) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0436(11) 0.0364(12) 0.0403(10) 0.0024(10) -0.0025(9) -0.0065(9)
C2 0.0414(11) 0.0376(12) 0.0362(10) 0.0017(9) -0.0048(9) -0.0036(8)
C3 0.0529(13) 0.0394(12) 0.0469(11) -0.0028(11) -0.0069(10) -0.0113(10)
C4 0.0539(13) 0.0497(14) 0.0454(12) 0.0032(12) 0.0026(11) -0.0160(11)
C5 0.0437(11) 0.0484(13) 0.0361(10) 0.0063(11) -0.0005(9) -0.0006(10)
C6 0.0429(11) 0.0390(11) 0.0488(11) -0.0058(10) 0.0004(10) -0.0053(10)
C7 0.0407(11) 0.0347(11) 0.0394(10) 0.0015(9) -0.0082(9) -0.0011(9)
C8 0.0545(14) 0.0438(14) 0.0556(13) -0.0065(13) -0.0033(11) -0.0057(11)
C9 0.0431(12) 0.0491(13) 0.0502(12) -0.0028(11) 0.0049(11) -0.0022(10)
C10 0.0435(11) 0.0437(12) 0.0552(12) 0.0059(12) 0.0110(11) 0.0042(11)
C11 0.0604(15) 0.0636(17) 0.0641(15) -0.0041(14) 0.0149(13) 0.0021(13)
N1 0.0400(10) 0.0401(10) 0.0446(10) -0.0048(9) 0.0013(8) -0.0045(8)
O1 0.0583(10) 0.0488(10) 0.0635(10) -0.0132(9) 0.0174(9) -0.0271(8)
O2 0.0600(10) 0.0545(10) 0.0643(10) 0.0098(9) -0.0022(9) -0.0192(9)
O3 0.0556(9) 0.0574(11) 0.0546(9) -0.0034(10) 0.0158(8) -0.0094(8)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
O1 C1 C6 120.3(2)
O1 C1 C2 121.6(2)
C6 C1 C2 118.12(19)
C3 C2 C7 121.0(2)
C3 C2 C1 118.0(2)
C7 C2 C1 120.95(19)
C4 C3 C2 122.5(2)
C4 C3 H3 118.7
C2 C3 H3 118.7
C3 C4 C5 119.1(2)
C3 C4 H4 120.4
C5 C4 H4 120.4
O3 C5 C6 124.7(2)
O3 C5 C4 114.3(2)
C6 C5 C4 121.0(2)
C5 C6 C1 121.1(2)
C5 C6 H6 119.4
C1 C6 H6 119.4
N1 C7 C2 119.1(2)
N1 C7 C8 119.3(2)
C2 C7 C8 121.6(2)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 C10 109.47(19)
N1 C9 H9A 109.8
C10 C9 H9A 109.8
N1 C9 H9B 109.8
C10 C9 H9B 109.8
H9A C9 H9B 108.2
O2 C10 C9 108.9(2)
O2 C10 H10A 109.9
C9 C10 H10A 109.9
O2 C10 H10B 109.9
C9 C10 H10B 109.9
H10A C10 H10B 108.3
O3 C11 H11A 109.5
O3 C11 H11B 109.5
H11A C11 H11B 109.5
O3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C7 N1 C9 127.16(19)
C7 N1 H1 116.4
C9 N1 H1 116.4
C10 O2 H2A 109.5
C5 O3 C11 118.10(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.291(3)
C1 C6 1.420(3)
C1 C2 1.434(3)
C2 C3 1.416(3)
C2 C7 1.433(3)
C3 C4 1.359(3)
C3 H3 0.93
C4 C5 1.403(4)
C4 H4 0.93
C5 O3 1.361(3)
C5 C6 1.366(3)
C6 H6 0.93
C7 N1 1.302(3)
C7 C8 1.500(3)
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
C9 N1 1.458(3)
C9 C10 1.504(3)
C9 H9A 0.97
C9 H9B 0.97
C10 O2 1.408(3)
C10 H10A 0.97
C10 H10B 0.97
C11 O3 1.422(4)
C11 H11A 0.96
C11 H11B 0.96
C11 H11C 0.96
N1 H1 0.86
O2 H2A 0.82
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
O2 H2A O1 4_477 0.82 1.91 2.708(2) 164
N1 H1 O1 . 0.86 1.80 2.533(3) 141
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 -179.6(2)
C6 C1 C2 C3 0.2(3)
O1 C1 C2 C7 1.2(3)
C6 C1 C2 C7 -179.0(2)
C7 C2 C3 C4 178.8(2)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 0.7(4)
C3 C4 C5 O3 178.5(2)
C3 C4 C5 C6 -0.8(4)
O3 C5 C6 C1 -178.6(2)
C4 C5 C6 C1 0.7(3)
O1 C1 C6 C5 179.5(2)
C2 C1 C6 C5 -0.3(3)
C3 C2 C7 N1 179.2(2)
C1 C2 C7 N1 -1.6(3)
C3 C2 C7 C8 -1.1(3)
C1 C2 C7 C8 178.1(2)
N1 C9 C10 O2 -69.5(2)
C2 C7 N1 C9 177.14(19)
C8 C7 N1 C9 -2.6(3)
C10 C9 N1 C7 -173.2(2)
C6 C5 O3 C11 0.0(4)
C4 C5 O3 C11 -179.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655031
