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#$Date: 2024-02-05 14:09:55 +0200 (Mon, 05 Feb 2024) $
#$Revision: 289697 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570452.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_1570452
loop_
_publ_author_name
'Sacharczuk, Natalia'
'Olejniczak, Anna'
'Bujak, Maciej'
'Dziubek, Kamil Filip'
'Katrusiak, Andrzej'
'Podsiadło, Marcin'
_publ_section_title
;
 Conformation-aggregation interplay in the simplest aliphatic ethers
 probed under high pressure.
;
_journal_issue                   'Pt 1'
_journal_name_full               IUCrJ
_journal_page_first              57
_journal_page_last               61
_journal_paper_doi               10.1107/S2052252523009995
_journal_volume                  11
_journal_year                    2024
_chemical_formula_moiety         'C6 H14 O'
_chemical_formula_sum            'C6 H14 O'
_chemical_formula_weight         102.17
_chemical_name_systematic        'dipropyl ether'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.32(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.099(12)
_cell_length_b                   3.9465(3)
_cell_length_c                   14.649(8)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1230
_cell_measurement_theta_min      5.3170
_cell_volume                     520.5(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         5300000
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.317
_diffrn_measured_fraction_theta_max 0.296
_diffrn_measurement_device_type  'KUMA KM4-CCD, Eos'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.317
_diffrn_reflns_Laue_measured_fraction_max 0.296
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2594
_diffrn_reflns_point_group_measured_fraction_full 0.317
_diffrn_reflns_point_group_measured_fraction_max 0.296
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.273
_diffrn_reflns_theta_min         5.355
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       disc
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.077
_refine_diff_density_rms         0.022
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         310
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0445P)²+0.3422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                232
_reflns_number_total             310
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lq5055.cif
_cod_data_source_block           dipropyl_ether_phase_alpha_5_30GPa
_cod_depositor_comments
'Adding full bibliography for 1570433--1570452.cif.'
_cod_original_cell_volume        520.5(7)
_cod_database_code               1570452
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_exptl_absorpt_special_details
;
Data were collected at room temperature (295(2) K) and pressure of 5.50(2) GPa
(5300000 kPa).
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H12,H11), C2(H22,H21), C4(H41,H42), C5(H51,H52)
3.b Idealised Me refined as rotating group:
 C3(H33,H31,H32), C6(H63,H61,H62)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4627(19) 0.8650(7) 0.1325(8) 0.050(9) Uani 1 1 d . . . . .
C1 C 0.371(3) 0.7166(10) 0.0531(12) 0.023(12) Uani 1 1 d . U . . .
H12 H 0.409912 0.780801 -0.002578 0.028 Uiso 1 1 calc R U . . .
H11 H 0.375152 0.471618 0.058045 0.028 Uiso 1 1 calc R U . . .
C2 C 0.217(2) 0.8244(10) 0.0454(9) 0.049(11) Uani 1 1 d . . . . .
H22 H 0.213116 1.069016 0.051235 0.059 Uiso 1 1 calc R U . . .
H21 H 0.172236 0.726698 0.095760 0.059 Uiso 1 1 calc R U . . .
C3 C 0.127(2) 0.7196(10) -0.0455(8) 0.046(10) Uani 1 1 d . . . . .
H33 H 0.029615 0.820062 -0.050986 0.069 Uiso 1 1 calc R U . . .
H31 H 0.117300 0.477280 -0.047607 0.069 Uiso 1 1 calc R U . . .
H32 H 0.175853 0.795027 -0.095538 0.069 Uiso 1 1 calc R U . . .
C4 C 0.605(3) 0.7270(11) 0.1482(13) 0.033(14) Uani 1 1 d . . . . .
H41 H 0.658536 0.789594 0.097857 0.040 Uiso 1 1 calc R U . . .
H42 H 0.598453 0.481867 0.149304 0.040 Uiso 1 1 calc R U . . .
C5 C 0.693(2) 0.8507(9) 0.2395(8) 0.044(11) Uani 1 1 d . . . . .
H51 H 0.691123 1.096390 0.240938 0.052 Uiso 1 1 calc R U . . .
H52 H 0.644999 0.768628 0.290271 0.052 Uiso 1 1 calc R U . . .
C6 C 0.846(2) 0.7360(12) 0.2521(9) 0.066(10) Uani 1 1 d . . . . .
H63 H 0.896718 0.821768 0.309438 0.100 Uiso 1 1 calc R U . . .
H61 H 0.893893 0.817475 0.202188 0.100 Uiso 1 1 calc R U . . .
H62 H 0.848248 0.492831 0.253003 0.100 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 112.9(6) . . ?
O1 C1 H12 109.1 . . ?
O1 C1 H11 109.1 . . ?
H12 C1 H11 107.9 . . ?
C2 C1 O1 112.4(5) . . ?
C2 C1 H12 109.1 . . ?
C2 C1 H11 109.1 . . ?
C1 C2 H22 109.1 . . ?
C1 C2 H21 109.1 . . ?
C1 C2 C3 112.3(6) . . ?
H22 C2 H21 107.9 . . ?
C3 C2 H22 109.1 . . ?
C3 C2 H21 109.1 . . ?
C2 C3 H33 109.5 . . ?
C2 C3 H31 109.5 . . ?
C2 C3 H32 109.5 . . ?
H33 C3 H31 109.5 . . ?
H33 C3 H32 109.5 . . ?
H31 C3 H32 109.5 . . ?
O1 C4 H41 109.2 . . ?
O1 C4 H42 109.2 . . ?
O1 C4 C5 111.8(6) . . ?
H41 C4 H42 107.9 . . ?
C5 C4 H41 109.2 . . ?
C5 C4 H42 109.2 . . ?
C4 C5 H51 109.2 . . ?
C4 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C6 C5 C4 112.2(6) . . ?
C6 C5 H51 109.2 . . ?
C6 C5 H52 109.2 . . ?
C5 C6 H63 109.5 . . ?
C5 C6 H61 109.5 . . ?
C5 C6 H62 109.5 . . ?
H63 C6 H61 109.5 . . ?
H63 C6 H62 109.5 . . ?
H61 C6 H62 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.46(4) . ?
O1 C4 1.40(4) . ?
C1 H12 0.9700 . ?
C1 H11 0.9700 . ?
C1 C2 1.45(4) . ?
C2 H22 0.9700 . ?
C2 H21 0.9700 . ?
C2 C3 1.52(3) . ?
C3 H33 0.9600 . ?
C3 H31 0.9600 . ?
C3 H32 0.9600 . ?
C4 H41 0.9700 . ?
C4 H42 0.9700 . ?
C4 C5 1.53(4) . ?
C5 H51 0.9700 . ?
C5 H52 0.9700 . ?
C5 C6 1.45(3) . ?
C6 H63 0.9600 . ?
C6 H61 0.9600 . ?
C6 H62 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 170.2(4) . . . . ?
O1 C4 C5 C6 -174.3(4) . . . . ?
C1 O1 C4 C5 -172.0(4) . . . . ?
C4 O1 C1 C2 171.4(4) . . . . ?
