#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:03:16 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/27/7232753.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_7232753
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_formula_moiety         'C5 H3 N O'
_chemical_formula_sum            'C5 H3 N O'
_chemical_formula_weight         93.08
_chemical_melting_point          184
_chemical_name_common            2-furonitrile
_chemical_name_systematic        furan-2-carbonitrile
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.7880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2801(3)
_cell_length_b                   12.0768(7)
_cell_length_c                   7.2295(4)
_cell_measurement_reflns_used    9299
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7999
_cell_measurement_theta_min      6.1944
_cell_volume                     455.59(4)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_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 0.975
_diffrn_measured_fraction_theta_max 0.971
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10333
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.022
_diffrn_reflns_theta_min         7.202
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.24513
_exptl_absorpt_correction_T_min  0.07349
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             192
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          1.116
_exptl_crystal_size_mid          0.771
_exptl_crystal_size_min          0.726
_exptl_crystal_size_rad          0.250
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.075(9)
_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   1.066
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0361
_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)+(0.0667P)²+0.0818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                867
_reflns_number_total             870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00435a3.cif
_cod_data_source_block           10922
_cod_depositor_comments
'Adding full bibliography for 7232751--7232754.cif.'
_cod_database_code               7232753
_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   0.463
_shelx_estimated_absorpt_t_max   0.589
_shelx_res_file
;
TITL 10922sadabs in P2(1)/c
    10922.res
    created by SHELXL-2018/3 at 00:43:15 on 22-Jan-2019
CELL  1.54178   5.2801  12.0768   7.2295   90.000   98.788   90.000
ZERR     4.00   0.0003   0.0007   0.0004    0.000    0.001    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  20 12 4 4
MERG   2
FMAP   2
PLAN   20
SIZE     0.726   0.771   1.116
ACTA
BOND   $H
EQIV $1 x-1, y, z-1
HTAB C4 N1_$1
L.S.  30
TEMP  -173.00
WGHT    0.066700    0.081800
EXTI    0.075075
FVAR       2.42843
O1    4    0.826221    0.416603    0.372141    11.00000    0.03157    0.04046 =
         0.03242    0.00176    0.00687   -0.00239
N1    3    0.960926    0.348958    0.834668    11.00000    0.03847    0.04253 =
         0.03748    0.00349    0.00437   -0.00121
C2    1    0.699121    0.373419    0.507344    11.00000    0.03184    0.02753 =
         0.03275    0.00025    0.00843    0.00160
C3    1    0.452259    0.351116    0.437117    11.00000    0.02994    0.03030 =
         0.04009    0.00075    0.00669    0.00047
H3    2    0.331529    0.322826    0.504020    11.00000   -1.20000
C4    1    0.421104    0.381598    0.245702    11.00000    0.03446    0.03227 =
         0.03615   -0.00356    0.00046    0.00249
H4    2    0.267517    0.377420    0.154060    11.00000   -1.20000
C5    1    0.649617    0.419827    0.214013    11.00000    0.03930    0.04068 =
         0.02999    0.00048    0.00537    0.00326
H5    2    0.710882    0.447790    0.104392    11.00000   -1.20000
C6    1    0.844556    0.359933    0.688208    11.00000    0.03120    0.03071 =
         0.03606   -0.00021    0.00788   -0.00040
HKLF    4




REM  10922sadabs in P2(1)/c
REM wR2 = 0.1045, GooF = S = 1.066, Restrained GooF = 1.066 for all data
REM R1 = 0.0361 for 867 Fo > 4sig(Fo) and 0.0361 for all 870 data
REM 74 parameters refined using 0 restraints

END

WGHT      0.0531      0.0883

REM Highest difference peak  0.200,  deepest hole -0.153,  1-sigma level  0.038
Q1    1   0.5654  0.3858  0.5025  11.00000  0.05    0.20
Q2    1   0.8025  0.3547  0.7815  11.00000  0.05    0.17
Q3    1   0.7586  0.3555  0.6043  11.00000  0.05    0.16
Q4    1   1.0450  0.3366  0.9634  11.00000  0.05    0.16
Q5    1   0.4183  0.3736  0.3455  11.00000  0.05    0.15
Q6    1   0.2797  0.2929  0.4672  11.00000  0.05    0.12
Q7    1   0.5182  0.4354  0.2460  11.00000  0.05    0.12
Q8    1   0.3322  0.3727  0.1919  11.00000  0.05    0.12
Q9    1   0.5395  0.3693  0.1917  11.00000  0.05    0.12
Q10   1   1.0040  0.3501  0.7269  11.00000  0.05    0.12
Q11   1   0.9803  0.4608  0.4070  11.00000  0.05    0.11
Q12   1   0.7254  0.4312  0.2882  11.00000  0.05    0.10
Q13   1   0.6531  0.4386  0.1344  11.00000  0.05    0.10
Q14   1   0.7625  0.4017  0.0865  11.00000  0.05    0.10
Q15   1   0.7299  0.3996  0.4750  11.00000  0.05    0.10
Q16   1   0.1792  0.2567  0.6054  11.00000  0.05    0.09
Q17   1   0.7478  0.4970  0.1073  11.00000  0.05    0.09
Q18   1   0.8407  0.4592  0.1524  11.00000  0.05    0.08
Q19   1   0.6273  0.4593  0.0984  11.00000  0.05    0.08
Q20   1   0.5719  0.4946  0.0566  11.00000  0.05    0.08
;
_shelx_res_checksum              50743
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_adp
O1 O 0.82622(14) 0.41660(7) 0.37214(11) 0.0346(3) Uani 1 1 d .
N1 N 0.9609(2) 0.34896(9) 0.83467(14) 0.0396(3) Uani 1 1 d .
C2 C 0.6991(2) 0.37342(9) 0.50734(16) 0.0303(3) Uani 1 1 d .
C3 C 0.4523(2) 0.35112(10) 0.43712(16) 0.0333(3) Uani 1 1 d .
H3 H 0.332(3) 0.3228(12) 0.5040(19) 0.040 Uiso 1 1 d U
C4 C 0.4211(2) 0.38160(10) 0.24570(17) 0.0348(4) Uani 1 1 d .
H4 H 0.268(3) 0.3774(12) 0.154(2) 0.042 Uiso 1 1 d U
C5 C 0.6496(2) 0.41983(10) 0.21401(16) 0.0366(4) Uani 1 1 d .
H5 H 0.711(3) 0.4478(13) 0.104(2) 0.044 Uiso 1 1 d U
C6 C 0.8446(2) 0.35993(9) 0.68821(15) 0.0324(3) Uani 1 1 d .
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 0.0316(5) 0.0405(6) 0.0324(5) 0.0018(3) 0.0069(3) -0.0024(3)
N1 0.0385(6) 0.0425(7) 0.0375(6) 0.0035(4) 0.0044(4) -0.0012(4)
C2 0.0318(6) 0.0275(6) 0.0328(6) 0.0002(4) 0.0084(4) 0.0016(4)
C3 0.0299(6) 0.0303(6) 0.0401(7) 0.0008(4) 0.0067(5) 0.0005(4)
C4 0.0345(6) 0.0323(7) 0.0361(6) -0.0036(4) 0.0005(5) 0.0025(4)
C5 0.0393(7) 0.0407(7) 0.0300(6) 0.0005(4) 0.0054(5) 0.0033(5)
C6 0.0312(6) 0.0307(6) 0.0361(7) -0.0002(4) 0.0079(5) -0.0004(4)
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'
N N 0.0311 0.0180 '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 105.23(9)
C3 C2 O1 110.92(10)
C3 C2 C6 132.64(11)
O1 C2 C6 116.44(9)
C2 C3 C4 106.05(11)
C2 C3 H3 125.5(9)
C4 C3 H3 128.4(9)
C5 C4 C3 106.41(10)
C5 C4 H4 125.6(9)
C3 C4 H4 128.0(9)
C4 C5 O1 111.39(10)
C4 C5 H5 133.2(9)
O1 C5 H5 115.4(9)
N1 C6 C2 179.66(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.3610(14)
O1 C2 1.3705(14)
N1 C6 1.1478(15)
C2 C3 1.3517(16)
C2 C6 1.4210(15)
C3 C4 1.4170(17)
C3 H3 0.923(15)
C4 C5 1.3438(17)
C4 H4 0.967(16)
C5 H5 0.962(16)
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
C4 H4 N1 0.967(16) 2.632(16) 3.5614(15) 161.2(13) 1_454 yes
