#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/69/2216966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216966
loop_
_publ_author_name
'Perašínová, Lucia'
'Andicsová, Anita'
'Végh, Daniel'
'Kožíšek, Jozef'
_publ_section_title
;
 5-[(9H-Fluoren-9-ylidene)methyl]furan-2-carbonitrile
;
_journal_coeditor_code           BX2120
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o273
_journal_page_last               o273
_journal_paper_doi               10.1107/S1600536807065798
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C19 H11 N O'
_chemical_formula_moiety         'C19 H11 N O'
_chemical_formula_sum            'C19 H11 N O'
_chemical_formula_weight         269.29
_chemical_name_systematic
;
5-[(9H-Fluoren-9-ylidene)methyl]furan-2-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.899(3)
_cell_length_b                   5.6109(11)
_cell_length_c                   15.664(3)
_cell_measurement_reflns_used    7057
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      3.05
_cell_volume                     1357.7(5)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R CCD'
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi 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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27628
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.18
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Clark & Reid, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1210P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                1524
_reflns_number_total             2746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2120.cif
_cod_data_source_block           I
_cod_original_cell_volume        1357.6(5)
_cod_original_sg_symbol_Hall     -P_2yn
_cod_original_sg_symbol_H-M      P_21/n
_cod_database_code               2216966
_cod_database_fobs_code          2216966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C C1 0.17033(14) 0.6172(3) 0.88196(13) 0.0544(5) Uani d . 1
C C2 0.23065(15) 0.6471(4) 0.96102(15) 0.0680(6) Uani d . 1
H H2A 0.2259 0.7739 0.9978 0.082 Uiso calc R 1
C C3 0.29834(16) 0.4852(4) 0.98462(15) 0.0737(7) Uani d . 1
H H3A 0.3385 0.5046 1.0380 0.088 Uiso calc R 1
C C4 0.30765(16) 0.2974(4) 0.93141(16) 0.0741(7) Uani d . 1
H H4A 0.3537 0.1919 0.9484 0.089 Uiso calc R 1
C C5 0.24829(15) 0.2672(4) 0.85303(15) 0.0651(6) Uani d . 1
H H5A 0.2536 0.1400 0.8166 0.078 Uiso calc R 1
C C6 0.17991(13) 0.4280(3) 0.82809(13) 0.0538(5) Uani d . 1
C C7 0.10829(13) 0.4398(3) 0.75032(13) 0.0521(5) Uani d . 1
C C8 0.08974(15) 0.2931(4) 0.67850(14) 0.0602(6) Uani d . 1
H H8A 0.1248 0.1626 0.6747 0.072 Uiso calc R 1
C C9 0.01799(15) 0.3426(4) 0.61169(14) 0.0660(6) Uani d . 1
H H9A 0.0044 0.2436 0.5627 0.079 Uiso calc R 1
C C10 -0.03397(15) 0.5382(4) 0.61677(14) 0.0686(6) Uani d . 1
H H10A -0.0818 0.5685 0.5709 0.082 Uiso calc R 1
C C11 -0.01619(14) 0.6875(4) 0.68787(13) 0.0605(6) Uani d . 1
H H11A -0.0512 0.8188 0.6904 0.073 Uiso calc R 1
C C12 0.05522(13) 0.6391(3) 0.75621(12) 0.0518(5) Uani d . 1
C C13 0.09090(13) 0.7573(3) 0.84099(13) 0.0532(5) Uani d . 1
C C14 0.06414(15) 0.9425(3) 0.88210(14) 0.0599(6) Uani d . 1
H H14A 0.1013 0.9725 0.9365 0.072 Uiso calc R 1
C C15 -0.00743(14) 1.1057(3) 0.86312(14) 0.0577(6) Uani d . 1
C C16 -0.02863(18) 1.2789(4) 0.91496(15) 0.0737(7) Uani d . 1
H H16A 0.0017 1.3139 0.9720 0.088 Uiso calc R 1
C C17 -0.10323(17) 1.3964(4) 0.86887(16) 0.0732(7) Uani d . 1
H H17A -0.1314 1.5227 0.8886 0.088 Uiso calc R 1
C C18 -0.12551(15) 1.2896(4) 0.79073(16) 0.0647(6) Uani d . 1
C C19 -0.19420(18) 1.3303(4) 0.7165(2) 0.0743(7) Uani d . 1
N N1 -0.25096(16) 1.3660(4) 0.65689(17) 0.0953(7) Uani d . 1
O O1 -0.06784(9) 1.1091(2) 0.78554(9) 0.0624(4) Uani d . 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'
N N 0.0061 0.0033 '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_publ_flag
C2 C1 C6 119.0(2) ?
C2 C1 C13 130.90(19) ?
C6 C1 C13 110.13(18) ?
C1 C2 C3 119.1(2) ?
C1 C2 H2A 120.4 ?
C3 C2 H2A 120.4 ?
C4 C3 C2 121.9(2) ?
C4 C3 H3A 119.1 ?
C2 C3 H3A 119.1 ?
C5 C4 C3 119.2(2) ?
C5 C4 H4A 120.4 ?
C3 C4 H4A 120.4 ?
C4 C5 C6 119.8(2) ?
C4 C5 H5A 120.1 ?
C6 C5 H5A 120.1 ?
C1 C6 C5 121.0(2) ?
C1 C6 C7 107.29(17) ?
C5 C6 C7 131.70(19) ?
C8 C7 C12 120.82(19) ?
C8 C7 C6 129.27(19) ?
C12 C7 C6 109.90(17) ?
C7 C8 C9 118.7(2) ?
C7 C8 H8A 120.6 ?
C9 C8 H8A 120.6 ?
C8 C9 C10 120.78(19) ?
C8 C9 H9A 119.6 ?
C10 C9 H9A 119.6 ?
C11 C10 C9 121.3(2) ?
C11 C10 H10A 119.3 ?
C9 C10 H10A 119.3 ?
C10 C11 C12 118.7(2) ?
C10 C11 H11A 120.6 ?
C12 C11 H11A 120.6 ?
C11 C12 C7 119.62(18) ?
C11 C12 C13 132.57(18) ?
C7 C12 C13 107.81(17) ?
C14 C13 C12 133.0(2) ?
C14 C13 C1 122.10(19) ?
C12 C13 C1 104.83(17) ?
C13 C14 C15 136.0(2) ?
C13 C14 H14A 112.0 ?
C15 C14 H14A 112.0 ?
O1 C15 C16 107.54(19) ?
O1 C15 C14 123.50(18) ?
C16 C15 C14 129.0(2) ?
C15 C16 C17 109.2(2) ?
C15 C16 H16A 125.4 ?
C17 C16 H16A 125.4 ?
C18 C17 C16 105.7(2) ?
C18 C17 H17A 127.1 ?
C16 C17 H17A 127.1 ?
C17 C18 O1 110.3(2) ?
C17 C18 C19 132.0(2) ?
O1 C18 C19 117.7(2) yes
N1 C19 C18 178.7(3) ?
C15 O1 C18 107.23(16) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.386(3) ?
C1 C6 1.386(3) ?
C1 C13 1.497(3) ?
C2 C3 1.390(3) ?
C2 H2A 0.9300 ?
C3 C4 1.373(3) ?
C3 H3A 0.9300 ?
C4 C5 1.370(3) ?
C4 H4A 0.9300 ?
C5 C6 1.396(3) ?
C5 H5A 0.9300 ?
C6 C7 1.459(3) ?
C7 C8 1.369(3) ?
C7 C12 1.417(3) ?
C8 C9 1.381(3) ?
C8 H8A 0.9300 ?
C9 C10 1.387(3) ?
C9 H9A 0.9300 ?
C10 C11 1.368(3) ?
C10 H10A 0.9300 ?
C11 C12 1.390(3) ?
C11 H11A 0.9300 ?
C12 C13 1.473(3) ?
C13 C14 1.344(3) ?
C14 C15 1.436(3) ?
C14 H14A 0.9300 ?
C15 O1 1.359(2) yes
C15 C16 1.359(3) ?
C16 C17 1.399(3) ?
C16 H16A 0.9300 ?
C17 C18 1.333(3) ?
C17 H17A 0.9300 ?
C18 O1 1.381(2) yes
C18 C19 1.413(4) ?
C19 N1 1.152(3) ?
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
C11 H11A O1 1_555 0.93 2.27 3.034(3) 139.68
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
C6 C1 C2 C3 -0.8(3)
C13 C1 C2 C3 178.4(2)
C1 C2 C3 C4 0.6(3)
C2 C3 C4 C5 -0.5(4)
C3 C4 C5 C6 0.5(3)
C2 C1 C6 C5 0.9(3)
C13 C1 C6 C5 -178.45(18)
C2 C1 C6 C7 -179.96(18)
C13 C1 C6 C7 0.7(2)
C4 C5 C6 C1 -0.8(3)
C4 C5 C6 C7 -179.6(2)
C1 C6 C7 C8 179.8(2)
C5 C6 C7 C8 -1.2(4)
C1 C6 C7 C12 0.7(2)
C5 C6 C7 C12 179.7(2)
C12 C7 C8 C9 -0.1(3)
C6 C7 C8 C9 -179.15(19)
C7 C8 C9 C10 0.5(3)
C8 C9 C10 C11 -0.2(3)
C9 C10 C11 C12 -0.5(3)
C10 C11 C12 C7 0.8(3)
C10 C11 C12 C13 -178.6(2)
C8 C7 C12 C11 -0.5(3)
C6 C7 C12 C11 178.63(17)
C8 C7 C12 C13 178.99(18)
C6 C7 C12 C13 -1.8(2)
C11 C12 C13 C14 3.9(4)
C7 C12 C13 C14 -175.5(2)
C11 C12 C13 C1 -178.4(2)
C7 C12 C13 C1 2.1(2)
C2 C1 C13 C14 -3.0(3)
C6 C1 C13 C14 176.26(18)
C2 C1 C13 C12 179.0(2)
C6 C1 C13 C12 -1.7(2)
C12 C13 C14 C15 -1.0(4)
C1 C13 C14 C15 -178.4(2)
C13 C14 C15 O1 -4.3(4)
C13 C14 C15 C16 175.6(2)
O1 C15 C16 C17 -0.8(3)
C14 C15 C16 C17 179.3(2)
C15 C16 C17 C18 0.5(3)
C16 C17 C18 O1 0.0(3)
C16 C17 C18 C19 -179.5(2)
C16 C15 O1 C18 0.8(2)
C14 C15 O1 C18 -179.31(19)
C17 C18 O1 C15 -0.5(2)
C19 C18 O1 C15 179.08(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119688
