In situ cryocrystallization and solid-state structures of furfural and some derivatives
Seidel, Rüdiger W.; Goddard, Richard; Nöthling, Nils; Lehmann, Christian W.; CrystEngComm 21 (2019) 3295–; doi:10.1039/C9CE00435A

data_7232751
_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 H4 O2'
_chemical_formula_sum            'C5 H4 O2'
_chemical_formula_weight         96.08
_chemical_melting_point          236
_chemical_name_common            furfural
_chemical_name_systematic        furan-2-carbaldehyde
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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            12
_cell_length_a                   7.9261(19)
_cell_length_b                   11.402(3)
_cell_length_c                   15.557(4)
_cell_measurement_reflns_used    2812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      41.2538
_cell_measurement_theta_min      5.6877
_cell_volume                     1405.9(6)
_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 0.974
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            56988
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.001
_diffrn_reflns_theta_min         4.808
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.70460
_exptl_absorpt_correction_T_min  0.47992
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          1.343
_exptl_crystal_size_mid          0.522
_exptl_crystal_size_min          0.501
_exptl_crystal_size_rad          0.250
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 946 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0389
_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/[\s^2^(Fo^2^)+(0.0531P)^2^+0.4655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2336
_reflns_number_total             2485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00435a3.cif
_cod_data_source_block           10007
_cod_depositor_comments
'Adding full bibliography for 7232751--7232754.cif.'
_cod_original_cell_volume        1406.0(6)
_cod_database_code               7232751
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.660
_shelx_res_checksum              62599