#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/86/7208661.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_7208661
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                   4.9467(10)
_cell_length_b                   9.3791(19)
_cell_length_c                   9.834(2)
_cell_measurement_reflns_used    2301
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      4.35
_cell_volume                     456.25(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         970000
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.265
_diffrn_measured_fraction_theta_max 0.265
_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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            1954
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.54
_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    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     25
_refine_ls_number_reflns         284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0451
_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)+(0.0437P)²+0.3168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                268
_reflns_number_total             284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25372k.txt
_cod_data_source_block           23butdiol_0.97GPa
_cod_database_code               7208661
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 0.3111(4) -0.0548(2) 0.1948(8) 0.0241(7) Uiso 1 1 d .
H1 H 0.1650 -0.0960 0.1923 0.036 Uiso 1 1 calc R
O2 O 0.1896(5) 0.3167(2) 0.2944(7) 0.0241(7) Uiso 1 1 d .
H2 H 0.3430 0.3497 0.2965 0.029 Uiso 1 1 calc R
C1 C 0.0641(8) 0.1241(4) 0.0631(13) 0.0327(11) Uiso 1 1 d .
H11 H 0.0951 0.0597 -0.0112 0.049 Uiso 1 1 calc R
H12 H 0.0826 0.2205 0.0318 0.049 Uiso 1 1 calc R
H13 H -0.1150 0.1099 0.0982 0.049 Uiso 1 1 calc R
C2 C 0.2701(6) 0.0956(3) 0.1751(11) 0.0213(8) Uiso 1 1 d .
H21 H 0.4427 0.1359 0.1450 0.026 Uiso 1 1 calc R
C3 C 0.2014(7) 0.1645(3) 0.3149(11) 0.0214(8) Uiso 1 1 d .
H31 H 0.3475 0.1431 0.3790 0.026 Uiso 1 1 calc R
C4 C -0.0650(7) 0.1188(4) 0.3774(12) 0.0306(10) Uiso 1 1 d .
H41 H -0.1110 0.1823 0.4503 0.046 Uiso 1 1 calc R
H42 H -0.0485 0.0234 0.4119 0.046 Uiso 1 1 calc R
H43 H -0.2042 0.1216 0.3094 0.046 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 111.3(5)
O1 C2 C3 108.7(7)
C1 C2 C3 114.8(4)
O2 C3 C4 107.5(3)
O2 C3 C2 107.3(7)
C4 C3 C2 115.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.438(4)
O2 C3 1.442(4)
C1 C2 1.524(14)
C2 C3 1.556(13)
C3 C4 1.516(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 439888
