#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/86/7208660.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_7208660
loop_
_publ_author_name
'Podsiadło, Marcin'
'Patyk, Ewa'
'Katrusiak, Andrzej'
_publ_section_title
;
 Chiral aggregation hierarchy in high-pressure resolved 2-butanol and
 2,3-butanediol
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6419
_journal_paper_doi               10.1039/c2ce25372k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C4 H10 O2'
_chemical_formula_sum            'C4 H10 O2'
_chemical_formula_weight         90.12
_chemical_melting_point          298
_chemical_name_common            2,3-butanediol
_chemical_name_systematic
;
2,3-butanediol
;
_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                   4.9973(10)
_cell_length_b                   9.4478(19)
_cell_length_c                   10.076(2)
_cell_measurement_reflns_used    2886
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      4.31
_cell_volume                     475.72(16)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1997)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         720000
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.374
_diffrn_measured_fraction_theta_max 0.374
_diffrn_measurement_device_type  'KM-4 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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1832
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Correction for absorption of the diamond-anvil cell and the sample
were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
219, 461-467).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.085
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0369
_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)+(0.0525P)²+0.1868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                310
_reflns_number_total             318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25372k.txt
_cod_data_source_block           23butdiol_0.72GPa
_cod_database_code               7208660
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_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 0.3076(4) -0.05279(18) 0.1991(5) 0.045(2) Uani 1 1 d .
H1 H 0.1626 -0.0933 0.1966 0.067 Uiso 1 1 calc R
O2 O 0.1914(4) 0.31592(17) 0.2940(5) 0.041(2) Uani 1 1 d .
H2 H 0.3432 0.3488 0.2960 0.049 Uiso 1 1 calc R
C1 C 0.0668(7) 0.1246(4) 0.0674(9) 0.042(4) Uani 1 1 d .
H11 H 0.0992 0.0607 -0.0050 0.063 Uiso 1 1 calc R
H12 H 0.0859 0.2203 0.0370 0.063 Uiso 1 1 calc R
H13 H -0.1113 0.1105 0.1005 0.063 Uiso 1 1 calc R
C2 C 0.2687(5) 0.0961(3) 0.1783(8) 0.033(4) Uani 1 1 d .
H21 H 0.4407 0.1350 0.1490 0.040 Uiso 1 1 calc R
C3 C 0.2033(6) 0.1652(3) 0.3145(8) 0.031(3) Uani 1 1 d .
H31 H 0.3491 0.1443 0.3765 0.037 Uiso 1 1 calc R
C4 C -0.0573(6) 0.1204(3) 0.3765(8) 0.042(5) Uani 1 1 d .
H41 H -0.1008 0.1834 0.4481 0.063 Uiso 1 1 calc R
H42 H -0.0406 0.0256 0.4100 0.063 Uiso 1 1 calc R
H43 H -0.1966 0.1235 0.3110 0.063 Uiso 1 1 calc R
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'
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
O1 C2 C1 111.6(4)
O1 C2 C3 108.1(6)
C1 C2 C3 115.6(4)
O2 C3 C4 107.6(3)
O2 C3 C2 107.3(6)
C4 C3 C2 115.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.435(4)
O2 C3 1.440(3)
C1 C2 1.530(11)
C2 C3 1.555(11)
C3 C4 1.505(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 439888
