#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507669.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_4507669
loop_
_publ_author_name
'Kelley, Steven P.'
'Narita, Asako'
'Holbrey, John D.'
'Green, Keith D.'
'Reichert, W. Matthew'
'Rogers, Robin D.'
_publ_section_title
;
 Understanding the Effects of Ionicity in Salts, Solvates, Co-Crystals,
 Ionic Co-Crystals, and Ionic Liquids, Rather than Nomenclature, Is
 Critical to Understanding Their Behavior
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              965
_journal_paper_doi               10.1021/cg4000439
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C6 H13 N O3'
_chemical_formula_weight         147.17
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.784(7)
_cell_angle_beta                 75.451(7)
_cell_angle_gamma                79.003(7)
_cell_formula_units_Z            2
_cell_length_a                   5.8197(7)
_cell_length_b                   7.3820(8)
_cell_length_c                   9.6242(11)
_cell_measurement_reflns_used    1513
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.82
_cell_volume                     391.54(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6359
_diffrn_reflns_theta_full        29.73
_diffrn_reflns_theta_max         29.73
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0437
_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)+(0.0650P)²+0.0209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                1627
_reflns_number_total             2212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4000439_si_002.cif
_cod_data_source_block           MorOAc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.30155(17) 0.01296(12) 0.41025(11) 0.0383(3) Uani 1 1 d .
O2 O 0.60401(16) 0.64045(12) 0.14797(10) 0.0347(2) Uani 1 1 d .
O3 O 0.88438(15) 0.47566(12) 0.25182(9) 0.0334(2) Uani 1 1 d .
N1 N 0.34734(19) 0.37325(14) 0.27481(11) 0.0269(2) Uani 1 1 d .
H1A H 0.440(3) 0.466(2) 0.2357(15) 0.032 Uiso 1 1 d .
H1B H 0.188(3) 0.4202(19) 0.2632(15) 0.032 Uiso 1 1 d .
C1 C 0.2926(3) 0.05615(19) 0.26327(16) 0.0363(3) Uani 1 1 d .
H3C H 0.125(3) 0.099(2) 0.2532(16) 0.044 Uiso 1 1 d .
H1D H 0.357(3) -0.051(2) 0.2165(17) 0.044 Uiso 1 1 d .
C2 C 0.4388(2) 0.20559(19) 0.19361(14) 0.0328(3) Uani 1 1 d .
H2A H 0.608(3) 0.161(2) 0.2007(16) 0.039 Uiso 1 1 d .
H2B H 0.425(3) 0.240(2) 0.0952(17) 0.039 Uiso 1 1 d .
C3 C 0.3488(2) 0.32719(18) 0.42959(13) 0.0304(3) Uani 1 1 d .
H3A H 0.276(3) 0.436(2) 0.4823(15) 0.036 Uiso 1 1 d .
H3B H 0.515(3) 0.295(2) 0.4356(16) 0.036 Uiso 1 1 d .
C4 C 0.2077(3) 0.1721(2) 0.48940(15) 0.0366(3) Uani 1 1 d .
H4A H 0.216(3) 0.136(2) 0.5899(18) 0.044 Uiso 1 1 d .
H4B H 0.040(3) 0.209(2) 0.4895(16) 0.044 Uiso 1 1 d .
C5 C 0.8113(2) 0.60849(16) 0.17088(12) 0.0248(3) Uani 1 1 d .
C6 C 0.9814(2) 0.73993(19) 0.09256(15) 0.0364(3) Uani 1 1 d .
H6A H 1.1051(15) 0.7290(10) 0.1369(8) 0.055 Uiso 1 1 calc R
H6B H 0.9003(9) 0.8585(12) 0.0942(9) 0.055 Uiso 1 1 calc R
H5C H 1.0410(15) 0.7113(9) -0.0005(10) 0.055 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0419(6) 0.0284(5) 0.0470(6) 0.0088(4) -0.0166(4) -0.0114(4)
O2 0.0261(5) 0.0338(5) 0.0453(5) 0.0089(4) -0.0130(4) -0.0094(4)
O3 0.0250(5) 0.0356(5) 0.0385(5) 0.0078(4) -0.0095(4) -0.0067(4)
N1 0.0214(5) 0.0266(5) 0.0336(5) 0.0041(4) -0.0080(4) -0.0080(4)
C1 0.0381(8) 0.0296(7) 0.0468(8) -0.0049(6) -0.0183(6) -0.0069(5)
C2 0.0302(7) 0.0372(7) 0.0304(6) -0.0021(5) -0.0079(5) -0.0034(5)
C3 0.0294(7) 0.0331(6) 0.0306(6) -0.0021(5) -0.0072(5) -0.0101(5)
C4 0.0346(7) 0.0411(8) 0.0326(7) 0.0070(6) -0.0048(5) -0.0129(6)
C5 0.0238(6) 0.0252(5) 0.0256(5) -0.0033(4) -0.0035(4) -0.0070(4)
C6 0.0347(7) 0.0355(7) 0.0409(7) 0.0026(6) -0.0072(6) -0.0161(5)
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
C1 O1 C4 110.62(10)
C2 N1 C3 110.55(10)
O1 C1 C2 111.31(11)
N1 C2 C1 109.22(11)
N1 C3 C4 109.46(10)
O1 C4 C3 111.41(11)
O3 C5 O2 124.17(11)
O3 C5 C6 119.13(11)
O2 C5 C6 116.69(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4223(17)
O1 C4 1.4246(17)
O2 C5 1.2536(14)
O3 C5 1.2508(14)
N1 C2 1.4861(16)
N1 C3 1.4874(16)
C1 C2 1.5088(19)
C3 C4 1.5070(18)
C5 C6 1.5158(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10942589
