#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/27/7232754.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_7232754
loop_
_publ_author_name
'Seidel, Rüdiger W.'
'Goddard, Richard'
'Nöthling, Nils'
'Lehmann, Christian W.'
_publ_section_title
;
 In situ cryocrystallization and solid-state structures of furfural and
 some derivatives
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3295
_journal_paper_doi               10.1039/C9CE00435A
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C5 H6 O'
_chemical_formula_sum            'C5 H6 O'
_chemical_formula_weight         82.10
_chemical_melting_point          184
_chemical_name_systematic        2-methylfuran
_space_group_crystal_system      tetragonal
_space_group_IT_number           106
_space_group_name_Hall           'P 4c -2ab'
_space_group_name_H-M_alt        'P 42 b c'
_symmetry_space_group_name_Hall  'P 4c -2ab'
_symmetry_space_group_name_H-M   'P 42 b c'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-03-22 deposited with the CCDC.    2019-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4727(15)
_cell_length_b                   12.4727(15)
_cell_length_c                   6.0594(7)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      41.1263
_cell_measurement_theta_min      3.5436
_cell_volume                     942.65(19)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2018)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            36611
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_min         5.014
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.77536
_exptl_absorpt_correction_T_min  0.59579
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_crystal_size_rad          0.250
_refine_diff_density_max         0.087
_refine_diff_density_min         -0.078
_refine_diff_density_rms         0.019
_refine_ls_abs_structure_details
;
 Flack x determined using 367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         852
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0207
_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)+(0.0204P)²+0.1207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0509
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                839
_reflns_number_total             852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00435a3.cif
_cod_data_source_block           9966
_cod_depositor_comments
'Adding full bibliography for 7232751--7232754.cif.'
_cod_original_cell_volume        942.7(3)
_cod_database_code               7232754
_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.
;
_shelx_estimated_absorpt_t_min   0.566
_shelx_estimated_absorpt_t_max   0.739
_shelx_res_file
;
TITL 9966sadabs in P4(2)bc
    9966.res
    created by SHELXL-2018/3 at 23:49:39 on 21-Jan-2019
CELL  1.54178  12.4727  12.4727   6.0594   90.000   90.000   90.000
ZERR     8.00   0.0015   0.0015   0.0007    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y,   Z
SYMM  - Y,   X, 1/2 + Z
SYMM    Y, - X, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y,   Z
SYMM  1/2 - X, 1/2 + Y,   Z
SYMM  1/2 - Y, 1/2 - X, 1/2 + Z
SYMM  1/2 + Y, 1/2 + X, 1/2 + Z
SFAC  C    H    O
UNIT  40 48 8
MERG   2
FMAP   2
PLAN   20
ACTA
EQIV $1 y-1/2, x+1/2, z-1/2
HTAB C5 O1_$1
BOND   $H
CONF H6A C6 C2 O1
CONF H6B C6 C2 O1
CONF H6C C6 C2 O1
L.S.  10
TEMP  -173.00
SIZE 1.0 0.5 0.5
WGHT    0.020400    0.120700
EXTI    0.003183
FVAR       0.29682
O1    3    0.220752    0.532119    0.575175    11.00000    0.02424    0.02570 =
         0.02613   -0.00217   -0.00059    0.00491
C2    1    0.283548    0.441810    0.554957    11.00000    0.01984    0.02203 =
         0.02872    0.00341    0.00406    0.00199
C3    1    0.259210    0.390715    0.366207    11.00000    0.02718    0.02245 =
         0.02927   -0.00091    0.00415   -0.00043
H3    2    0.291493    0.327702    0.312075    11.00000   -1.20000
C4    1    0.176644    0.451426    0.259833    11.00000    0.02739    0.03084 =
         0.02492    0.00199   -0.00234   -0.00574
H4    2    0.143694    0.436599    0.124155    11.00000   -1.20000
C5    1    0.156474    0.535150    0.391007    11.00000    0.02232    0.03037 =
         0.03037    0.00450   -0.00216    0.00219
H5    2    0.108691    0.594939    0.381302    11.00000   -1.20000
C6    1    0.359065    0.421861    0.739094    11.00000    0.02770    0.04030 =
         0.03369    0.00260   -0.00434    0.00434
AFIX 137
H6A   2    0.405063    0.360672    0.702645    11.00000   -1.50000
H6B   2    0.318554    0.406097    0.873819    11.00000   -1.50000
H6C   2    0.403540    0.485615    0.762646    11.00000   -1.50000
AFIX   0
HKLF    4




REM  9966sadabs in P4(2)bc
REM wR2 = 0.0509, GooF = S = 1.100, Restrained GooF = 1.099 for all data
REM R1 = 0.0207 for 839 Fo > 4sig(Fo) and 0.0214 for all 852 data
REM 66 parameters refined using 1 restraints

END

WGHT      0.0204      0.1207

REM Highest difference peak  0.087,  deepest hole -0.078,  1-sigma level  0.019
Q1    1   0.1933  0.5226  0.2789  11.00000  0.05    0.09
Q2    1   0.3146  0.4304  0.4439  11.00000  0.05    0.08
Q3    1   0.3146  0.4185  0.6596  11.00000  0.05    0.08
Q4    1   0.2505  0.3921  0.5114  11.00000  0.05    0.06
Q5    1   0.2038  0.5386  0.7887  11.00000  0.05    0.06
Q6    1   0.0816  0.3980 -0.0265  11.00000  0.05    0.06
Q7    1   0.1402  0.6437  0.1524  11.00000  0.05    0.06
Q8    1   0.1314  0.4945  0.7313  11.00000  0.05    0.06
Q9    1   0.3447  0.3414  0.8982  11.00000  0.05    0.06
Q10   1   0.4292  0.4190  0.7117  11.00000  0.05    0.05
Q11   1   0.3281  0.2631  0.9212  11.00000  0.05    0.05
Q12   1   0.1867  0.5350  0.4679  11.00000  0.05    0.05
Q13   1   0.2628  0.5911  0.4151  11.00000  0.05    0.05
Q14   1   0.2456  0.3636  0.9958  11.00000  0.05    0.05
Q15   1   0.2468  0.6459  0.4046  11.00000  0.05    0.05
Q16   1   0.1449  0.4744  0.3618  11.00000  0.05    0.05
Q17   1   0.2505  0.4794  0.5707  11.00000  0.05    0.05
Q18   1   0.1301  0.4596 -0.1130  11.00000  0.05    0.05
Q19   1   0.2204  0.4064  0.3092  11.00000  0.05    0.04
Q20   1   0.3196  0.4392  0.8648  11.00000  0.05    0.04
;
_shelx_res_checksum              78497
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+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
O1 O 0.22075(7) 0.53212(6) 0.5752(2) 0.0254(3) Uani 1 1 d . .
C2 C 0.28355(9) 0.44181(9) 0.5550(3) 0.0235(3) Uani 1 1 d . .
C3 C 0.25921(11) 0.39071(11) 0.3662(3) 0.0263(3) Uani 1 1 d . .
H3 H 0.2915(13) 0.3277(13) 0.312(3) 0.032 Uiso 1 1 d . U
C4 C 0.17664(11) 0.45143(11) 0.2598(3) 0.0277(3) Uani 1 1 d . .
H4 H 0.1437(13) 0.4366(12) 0.124(3) 0.033 Uiso 1 1 d . U
C5 C 0.15647(11) 0.53515(11) 0.3910(3) 0.0277(3) Uani 1 1 d . .
H5 H 0.1087(14) 0.5949(14) 0.381(3) 0.033 Uiso 1 1 d . U
C6 C 0.35906(11) 0.42186(13) 0.7391(3) 0.0339(4) Uani 1 1 d . .
H6A H 0.405063 0.360672 0.702645 0.051 Uiso 1 1 calc R U
H6B H 0.318554 0.406097 0.873819 0.051 Uiso 1 1 calc R U
H6C H 0.403540 0.485615 0.762646 0.051 Uiso 1 1 calc R U
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 0.0242(5) 0.0257(5) 0.0261(5) -0.0022(5) -0.0006(5) 0.0049(3)
C2 0.0198(6) 0.0220(6) 0.0287(8) 0.0034(7) 0.0041(6) 0.0020(5)
C3 0.0272(6) 0.0224(6) 0.0293(7) -0.0009(6) 0.0042(6) -0.0004(5)
C4 0.0274(7) 0.0308(7) 0.0249(8) 0.0020(6) -0.0023(7) -0.0057(5)
C5 0.0223(6) 0.0304(7) 0.0304(9) 0.0045(7) -0.0022(7) 0.0022(5)
C6 0.0277(7) 0.0403(9) 0.0337(8) 0.0026(7) -0.0043(7) 0.0043(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C5 O1 C2 106.38(11)
C3 C2 O1 109.57(12)
C3 C2 C6 134.83(13)
O1 C2 C6 115.59(13)
C2 C3 C4 107.15(12)
C2 C3 H3 126.5(9)
C4 C3 H3 126.3(9)
C5 C4 C3 106.32(13)
C5 C4 H4 126.4(9)
C3 C4 H4 127.3(9)
C4 C5 O1 110.59(12)
C4 C5 H5 133.6(11)
O1 C5 H5 115.8(11)
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.375(2)
O1 C2 1.3774(15)
C2 C3 1.344(2)
C2 C6 1.481(2)
C3 C4 1.432(2)
C3 H3 0.942(17)
C4 C5 1.336(2)
C4 H4 0.938(19)
C5 H5 0.96(2)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O1 0.96(2) 2.611(19) 3.3804(18) 137.8(15) 8_454 yes
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
H6A C6 C2 O1 -174.1
H6B C6 C2 O1 65.9
H6C C6 C2 O1 -54.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10797
