#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/72/2237251.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_2237251
loop_
_publ_author_name
'Fang, Sin-Kai'
'Chang, Che-Wei'
'Tsai, Hsing-Yang'
'Luo, Ming-Hui'
'Chen, Kew-Yu'
_publ_section_title
;
 1-Methoxy-11H-benzo[b]fluoren-11-one
;
_journal_coeditor_code           XU5629
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o79
_journal_paper_doi               10.1107/S1600536812050076
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C18 H12 O2'
_chemical_formula_moiety         'C18 H12 O2'
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28
_chemical_name_systematic
;
1-Methoxy-11H-benzo[b]fluoren-11-one
;
_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                 99.935(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7202(3)
_cell_length_b                   9.2462(4)
_cell_length_c                   18.0294(8)
_cell_measurement_reflns_used    6867
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.3999
_cell_measurement_theta_min      2.6786
_cell_volume                     1267.68(9)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11580
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.418
_refine_ls_extinction_coef       0.041(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0834
_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)+(0.1046P)²+1.6820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2499
_reflns_number_gt                1881
_reflns_number_total             2559
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5629.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237251
_cod_database_fobs_code          2237251
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_symmetry_multiplicity
O O1 1.2838(3) 0.3051(3) 0.92283(15) 0.0675(8) Uani d . 1 1
O O2 1.3420(3) 0.0972(3) 1.04942(14) 0.0571(7) Uani d . 1 1
C C1 1.0841(4) 0.2264(3) 1.00540(17) 0.0428(7) Uani d . 1 1
C C2 1.1419(4) 0.3058(4) 0.94252(18) 0.0464(8) Uani d . 1 1
C C3 0.9836(4) 0.3911(3) 0.90635(17) 0.0439(7) Uani d . 1 1
C C4 0.9640(4) 0.4820(4) 0.84656(18) 0.0490(8) Uani d . 1 1
H H4 1.0571 0.4978 0.8209 0.059 Uiso calc R 1 1
C C5 0.8006(4) 0.5531(3) 0.82323(17) 0.0461(8) Uani d . 1 1
C C6 0.7726(5) 0.6517(4) 0.7623(2) 0.0579(9) Uani d . 1 1
H H6 0.8634 0.6712 0.7360 0.069 Uiso calc R 1 1
C C7 0.6147(6) 0.7183(4) 0.7419(2) 0.0683(11) Uani d . 1 1
H H7 0.5990 0.7835 0.7020 0.082 Uiso calc R 1 1
C C8 0.4773(6) 0.6901(4) 0.7796(2) 0.0694(11) Uani d . 1 1
H H8 0.3696 0.7359 0.7646 0.083 Uiso calc R 1 1
C C9 0.4978(5) 0.5959(4) 0.8385(2) 0.0578(9) Uani d . 1 1
H H9 0.4038 0.5780 0.8633 0.069 Uiso calc R 1 1
C C10 0.6602(4) 0.5249(3) 0.86266(19) 0.0475(8) Uani d . 1 1
C C11 0.6857(4) 0.4280(3) 0.92502(19) 0.0473(8) Uani d . 1 1
H H11 0.5937 0.4089 0.9508 0.057 Uiso calc R 1 1
C C12 0.8438(4) 0.3637(3) 0.94670(17) 0.0401(7) Uani d . 1 1
C C13 0.9079(4) 0.2608(3) 1.00807(17) 0.0420(7) Uani d . 1 1
C C14 0.8220(4) 0.2001(4) 1.0611(2) 0.0522(8) Uani d . 1 1
H H14 0.7052 0.2224 1.0625 0.063 Uiso calc R 1 1
C C15 0.9155(5) 0.1040(4) 1.1126(2) 0.0589(9) Uani d . 1 1
H H15 0.8600 0.0626 1.1493 0.071 Uiso calc R 1 1
C C16 1.0877(5) 0.0687(4) 1.1106(2) 0.0544(9) Uani d . 1 1
H H16 1.1465 0.0040 1.1458 0.065 Uiso calc R 1 1
C C17 1.1749(4) 0.1289(4) 1.05646(18) 0.0471(8) Uani d . 1 1
C C18 1.4337(5) -0.0107(4) 1.0985(2) 0.0627(10) Uani d . 1 1
H H18A 1.4545 0.0248 1.1493 0.094 Uiso calc R 1 1
H H18B 1.5440 -0.0321 1.0832 0.094 Uiso calc R 1 1
H H18C 1.3638 -0.0971 1.0958 0.094 Uiso calc R 1 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
C17 O2 C18 118.0(3)
C17 C1 C13 120.3(3)
C17 C1 C2 130.1(3)
C13 C1 C2 109.5(3)
O1 C2 C1 129.0(3)
O1 C2 C3 125.8(3)
C1 C2 C3 105.2(3)
C4 C3 C12 121.8(3)
C4 C3 C2 129.8(3)
C12 C3 C2 108.4(3)
C3 C4 C5 119.6(3)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C10 118.7(3)
C6 C5 C4 122.4(3)
C10 C5 C4 118.9(3)
C7 C6 C5 120.8(4)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C8 120.8(4)
C6 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C7 120.6(4)
C9 C8 H8 119.7
C7 C8 H8 119.7
C8 C9 C10 120.9(4)
C8 C9 H9 119.5
C10 C9 H9 119.5
C9 C10 C5 118.2(3)
C9 C10 C11 121.9(3)
C5 C10 C11 119.8(3)
C12 C11 C10 119.9(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C3 120.0(3)
C11 C12 C13 131.9(3)
C3 C12 C13 108.2(3)
C14 C13 C1 121.2(3)
C14 C13 C12 130.1(3)
C1 C13 C12 108.7(3)
C13 C14 C15 117.9(3)
C13 C14 H14 121.1
C15 C14 H14 121.1
C16 C15 C14 121.8(3)
C16 C15 H15 119.1
C14 C15 H15 119.1
C15 C16 C17 120.6(3)
C15 C16 H16 119.7
C17 C16 H16 119.7
O2 C17 C1 117.4(3)
O2 C17 C16 124.3(3)
C1 C17 C16 118.3(3)
O2 C18 H18A 109.5
O2 C18 H18B 109.5
H18A C18 H18B 109.5
O2 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.208(4)
O2 C17 1.350(4)
O2 C18 1.436(4)
C1 C17 1.389(5)
C1 C13 1.406(4)
C1 C2 1.483(4)
C2 C3 1.505(4)
C3 C4 1.355(5)
C3 C12 1.424(4)
C4 C5 1.421(5)
C4 H4 0.9300
C5 C6 1.415(5)
C5 C10 1.419(5)
C6 C7 1.359(5)
C6 H6 0.9300
C7 C8 1.379(6)
C7 H7 0.9300
C8 C9 1.363(6)
C8 H8 0.9300
C9 C10 1.416(5)
C9 H9 0.9300
C10 C11 1.425(5)
C11 C12 1.354(4)
C11 H11 0.9300
C12 C13 1.478(4)
C13 C14 1.374(4)
C14 C15 1.394(5)
C14 H14 0.9300
C15 C16 1.375(5)
C15 H15 0.9300
C16 C17 1.394(5)
C16 H16 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C7 H7 O1 2_756 0.93 2.57 3.299(5) 135
C11 H11 O1 1_455 0.93 2.55 3.298(4) 138
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
C17 C1 C2 O1 -1.7(6)
C13 C1 C2 O1 179.4(3)
C17 C1 C2 C3 178.3(3)
C13 C1 C2 C3 -0.6(3)
O1 C2 C3 C4 0.0(6)
C1 C2 C3 C4 180.0(3)
O1 C2 C3 C12 -179.3(3)
C1 C2 C3 C12 0.7(3)
C12 C3 C4 C5 0.3(5)
C2 C3 C4 C5 -178.9(3)
C3 C4 C5 C6 178.6(3)
C3 C4 C5 C10 -1.1(5)
C10 C5 C6 C7 0.0(5)
C4 C5 C6 C7 -179.6(3)
C5 C6 C7 C8 -0.7(6)
C6 C7 C8 C9 0.6(6)
C7 C8 C9 C10 0.1(6)
C8 C9 C10 C5 -0.7(5)
C8 C9 C10 C11 178.8(3)
C6 C5 C10 C9 0.7(4)
C4 C5 C10 C9 -179.7(3)
C6 C5 C10 C11 -178.9(3)
C4 C5 C10 C11 0.7(4)
C9 C10 C11 C12 -179.2(3)
C5 C10 C11 C12 0.3(5)
C10 C11 C12 C3 -1.1(5)
C10 C11 C12 C13 179.8(3)
C4 C3 C12 C11 0.8(5)
C2 C3 C12 C11 -179.9(3)
C4 C3 C12 C13 -179.9(3)
C2 C3 C12 C13 -0.6(3)
C17 C1 C13 C14 0.4(5)
C2 C1 C13 C14 179.4(3)
C17 C1 C13 C12 -178.7(3)
C2 C1 C13 C12 0.2(3)
C11 C12 C13 C14 0.4(6)
C3 C12 C13 C14 -178.8(3)
C11 C12 C13 C1 179.4(3)
C3 C12 C13 C1 0.2(3)
C1 C13 C14 C15 0.5(5)
C12 C13 C14 C15 179.4(3)
C13 C14 C15 C16 -0.7(5)
C14 C15 C16 C17 0.1(6)
C18 O2 C17 C1 -175.9(3)
C18 O2 C17 C16 3.1(5)
C13 C1 C17 O2 178.0(3)
C2 C1 C17 O2 -0.7(5)
C13 C1 C17 C16 -1.0(5)
C2 C1 C17 C16 -179.7(3)
C15 C16 C17 O2 -178.2(3)
C15 C16 C17 C1 0.8(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658293
