#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/79/2227981.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_2227981
loop_
_publ_author_name
'Shalumova, Tamila'
'Tanski, Joseph M.'
_publ_section_title
;
 5-(Hydroxymethyl)furan-2-carbaldehyde
;
_journal_coeditor_code           SI2283
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2266
_journal_paper_doi               10.1107/S1600536810031119
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H6 O3'
_chemical_formula_moiety         'C6 H6 O3'
_chemical_formula_sum            'C6 H6 O3'
_chemical_formula_weight         126.11
_chemical_melting_point_gt       301
_chemical_melting_point_lt       307
_chemical_name_common            5-Hydroxymethylfurfural
_chemical_name_systematic
;
5-(Hydroxymethyl)furan-2-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 90.770(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.9126(17)
_cell_length_b                   5.6166(6)
_cell_length_c                   13.1722(14)
_cell_measurement_reflns_used    5970
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.56
_cell_volume                     1177.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15720
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0367P)²+0.3118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                2246
_reflns_number_total             2933
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2283.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227981
_cod_database_fobs_code          2227981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O11 1.11183(6) 0.07149(19) 0.62286(8) 0.0320(2) Uani d . 1 . .
O O12 0.94229(6) 0.19067(16) 0.61025(7) 0.0227(2) Uani d . 1 . .
O O13 0.77247(6) 0.02624(17) 0.68104(8) 0.0268(2) Uani d D 1 . .
H H13O 0.7607(10) 0.125(3) 0.7278(11) 0.032 Uiso d D 1 . .
O O21 0.44841(6) -0.14117(17) 0.33477(7) 0.0259(2) Uani d . 1 . .
O O22 0.38382(5) 0.01084(15) 0.52416(6) 0.01771(19) Uani d . 1 . .
O O23 0.25895(6) -0.14054(16) 0.67299(7) 0.0229(2) Uani d D 1 . .
H H23O 0.2152(9) -0.064(3) 0.6587(12) 0.027 Uiso d D 1 . .
C C11 1.08966(9) 0.2796(3) 0.63013(10) 0.0278(3) Uani d . 1 . .
H H11A 1.1321 0.3966 0.6401 0.033 Uiso calc R 1 . .
C C12 1.00405(9) 0.3586(2) 0.62456(10) 0.0246(3) Uani d . 1 . .
C C13 0.96973(10) 0.5808(3) 0.62951(10) 0.0295(3) Uani d . 1 . .
H H13B 0.9989 0.7269 0.6386 0.035 Uiso calc R 1 . .
C C14 0.88169(10) 0.5496(3) 0.61829(10) 0.0290(3) Uani d . 1 . .
H H14A 0.8402 0.6713 0.6189 0.035 Uiso calc R 1 . .
C C15 0.86787(8) 0.3121(2) 0.60650(10) 0.0230(3) Uani d . 1 . .
C C16 0.79019(9) 0.1669(3) 0.59398(10) 0.0271(3) Uani d . 1 . .
H H16A 0.7421 0.2743 0.5801 0.032 Uiso calc R 1 . .
H H16B 0.7964 0.0608 0.5345 0.032 Uiso calc R 1 . .
C C21 0.44388(8) 0.0692(2) 0.35668(10) 0.0209(3) Uani d . 1 . .
H H21A 0.4642 0.1803 0.3085 0.025 Uiso calc R 1 . .
C C22 0.41029(7) 0.1641(2) 0.44951(9) 0.0187(3) Uani d . 1 . .
C C23 0.39749(8) 0.3945(2) 0.47805(10) 0.0220(3) Uani d . 1 . .
H H23B 0.4111 0.5334 0.4405 0.026 Uiso calc R 1 . .
C C24 0.35976(8) 0.3853(2) 0.57519(10) 0.0235(3) Uani d . 1 . .
H H24A 0.3423 0.5172 0.6149 0.028 Uiso calc R 1 . .
C C25 0.35344(8) 0.1518(2) 0.60018(9) 0.0186(3) Uani d . 1 . .
C C26 0.32435(8) 0.0284(2) 0.69336(10) 0.0215(3) Uani d . 1 . .
H H26A 0.3726 -0.0546 0.7257 0.026 Uiso calc R 1 . .
H H26B 0.3037 0.1486 0.7420 0.026 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 O12 C12 . . 106.27(10) ?
C16 O13 H13O . . 105.8(11) ?
C25 O22 C22 . . 105.96(9) ?
C26 O23 H23O . . 107.5(11) ?
O11 C11 C12 . . 124.46(13) ?
O11 C11 H11A . . 117.8 ?
C12 C11 H11A . . 117.8 ?
C13 C12 O12 . . 110.41(12) ?
C13 C12 C11 . . 131.41(14) ?
O12 C12 C11 . . 118.17(12) ?
C12 C13 C14 . . 106.13(13) ?
C12 C13 H13B . . 126.9 ?
C14 C13 H13B . . 126.9 ?
C15 C14 C13 . . 106.91(13) ?
C15 C14 H14A . . 126.5 ?
C13 C14 H14A . . 126.5 ?
C14 C15 O12 . . 110.28(12) ?
C14 C15 C16 . . 133.06(13) ?
O12 C15 C16 . . 116.63(11) ?
O13 C16 C15 . . 112.84(11) ?
O13 C16 H16A . . 109.0 ?
C15 C16 H16A . . 109.0 ?
O13 C16 H16B . . 109.0 ?
C15 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
O21 C21 C22 . . 125.62(12) ?
O21 C21 H21A . . 117.2 ?
C22 C21 H21A . . 117.2 ?
C23 C22 O22 . . 110.37(11) ?
C23 C22 C21 . . 129.96(12) ?
O22 C22 C21 . . 119.65(11) ?
C22 C23 C24 . . 106.27(11) ?
C22 C23 H23B . . 126.9 ?
C24 C23 H23B . . 126.9 ?
C25 C24 C23 . . 106.68(11) ?
C25 C24 H24A . . 126.7 ?
C23 C24 H24A . . 126.7 ?
C24 C25 O22 . . 110.71(11) ?
C24 C25 C26 . . 132.47(12) ?
O22 C25 C26 . . 116.75(11) ?
O23 C26 C25 . . 112.81(10) ?
O23 C26 H26A . . 109.0 ?
C25 C26 H26A . . 109.0 ?
O23 C26 H26B . . 109.0 ?
C25 C26 H26B . . 109.0 ?
H26A C26 H26B . . 107.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C11 . 1.2249(18) ?
O12 C15 . 1.3670(15) ?
O12 C12 . 1.3732(16) ?
O13 C16 . 1.4239(17) ?
O13 H13O . 0.850(13) ?
O21 C21 . 1.2188(16) ?
O22 C25 . 1.3698(14) ?
O22 C22 . 1.3769(14) ?
O23 C26 . 1.4312(16) ?
O23 H23O . 0.838(13) ?
C11 C12 . 1.434(2) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.364(2) ?
C13 C14 . 1.418(2) ?
C13 H13B . 0.9500 ?
C14 C15 . 1.360(2) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.488(2) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C21 C22 . 1.4431(17) ?
C21 H21A . 0.9500 ?
C22 C23 . 1.3639(18) ?
C23 C24 . 1.4217(19) ?
C23 H23B . 0.9500 ?
C24 C25 . 1.3561(18) ?
C24 H24A . 0.9500 ?
C25 C26 . 1.4888(18) ?
C26 H26A . 0.9900 ?
C26 H26B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O13 H13O O23 2_656 0.850(13) 1.886(13) 2.7341(13) 175.4(16)
O23 H23O O11 1_455 0.838(13) 1.867(13) 2.7006(14) 173.0(16)
C14 H14A O13 1_565 0.95 2.41 3.3029(17) 155.5
C21 H21A O21 2_655 0.95 2.56 3.4726(15) 160.4
C23 H23B O21 1_565 0.95 2.38 3.3258(16) 175.0
C24 H24A O23 1_565 0.95 2.46 3.3734(16) 160.3
C26 H26A O21 4_556 0.99 2.53 3.4639(16) 157.6
