#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:05:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180465 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/34/7213441.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213441
loop_
_publ_author_name
'O’Leary, Jane'
'Bell, Paul C.'
'Wallis, John D.'
'Schweizer, W. Bernd'
_publ_section_title
;
 Attractive and repulsive effects in the interactions between
 electron-rich and electron-deficient groups in peri-substituted
 naphthalenes
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              133
_journal_paper_doi               10.1039/b008226k
_journal_year                    2001
_chemical_formula_sum            'C18 H16 O5'
_chemical_formula_weight         312.31
_chemical_name_systematic
; 
5-(8'-Methoxynaphthyl-1'-methylidene)-1,3-dioxan-4,6-dione 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.42
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.291(2)
_cell_length_b                   11.607(3)
_cell_length_c                   12.988(3)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      19.8
_cell_volume                     1495.5(6)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        'MolEN (Enraf-Nonius, 1990)'
_computing_molecular_graphics    'PLUTO, ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       ο/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1340
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         5.87
_diffrn_standards_decay_%        .7
_diffrn_standards_interval_time  10000s
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  0.8841
_exptl_absorpt_correction_T_min  0.8171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(15)
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         1317
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.837
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                1317
_reflns_number_total             1340
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            b008226ksup1.cif
_cod_data_source_block           X27079
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7213441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
O19 O 0.50191(14) -0.25254(12) 0.15373(12) 0.0168(3) Uani 1 1 d
O20 O 0.47724(13) -0.12561(13) 0.00810(11) 0.0162(3) Uani 1 1 d
O21 O 0.61092(14) -0.19751(12) 0.31659(12) 0.0184(3) Uani 1 1 d
O22 O 0.56349(15) 0.04963(12) 0.03241(12) 0.0191(3) Uani 1 1 d
O23 O 0.75998(14) 0.13382(13) 0.35214(12) 0.0198(3) Uani 1 1 d
C1 C 0.49819(19) 0.15765(17) 0.22401(16) 0.0145(4) Uani 1 1 d
C2 C 0.37019(19) 0.17501(19) 0.15712(17) 0.0186(4) Uani 1 1 d
C3 C 0.3215(2) 0.28706(19) 0.12814(17) 0.0201(4) Uani 1 1 d
C4 C 0.3994(2) 0.38070(19) 0.16467(18) 0.0197(4) Uani 1 1 d
C5 C 0.6163(2) 0.46511(17) 0.26480(17) 0.0197(5) Uani 1 1 d
C6 C 0.7451(2) 0.45083(18) 0.32837(18) 0.0209(5) Uani 1 1 d
C7 C 0.7973(2) 0.33965(19) 0.35949(17) 0.0182(4) Uani 1 1 d
C8 C 0.7172(2) 0.24423(17) 0.32728(17) 0.0161(4) Uani 1 1 d
C9 C 0.5821(2) 0.25479(17) 0.26255(17) 0.0145(4) Uani 1 1 d
C10 C 0.5322(2) 0.36801(18) 0.23157(16) 0.0167(4) Uani 1 1 d
C11 C 0.53817(18) 0.03758(17) 0.25586(16) 0.0142(4) Uani 1 1 d
C12 C 0.53629(19) -0.04895(16) 0.18678(17) 0.0147(4) Uani 1 1 d
C13 C 0.55417(19) -0.16932(17) 0.22719(16) 0.0139(4) Uani 1 1 d
C14 C 0.41557(19) -0.21902(16) 0.05078(16) 0.0160(4) Uani 1 1 d
C15 C 0.52519(18) -0.03276(16) 0.07149(16) 0.0147(4) Uani 1 1 d
C16 C 0.4156(2) -0.31964(19) -0.02210(18) 0.0216(5) Uani 1 1 d
C17 C 0.2765(2) -0.18562(19) 0.06000(17) 0.0204(4) Uani 1 1 d
C18 C 0.9029(2) 0.1154(2) 0.38721(19) 0.0221(4) Uani 1 1 d
H1 H 0.315(4) 0.104(3) 0.134(3) 0.042(9) Uiso 1 1 d
H2 H 0.235(4) 0.297(3) 0.072(3) 0.049(10) Uiso 1 1 d
H3 H 0.366(3) 0.454(3) 0.148(3) 0.035(8) Uiso 1 1 d
H4 H 0.584(3) 0.540(2) 0.242(2) 0.017(6) Uiso 1 1 d
H5 H 0.800(3) 0.520(3) 0.352(2) 0.025(7) Uiso 1 1 d
H6 H 0.884(3) 0.334(2) 0.404(2) 0.023(7) Uiso 1 1 d
H7 H 0.550(2) 0.014(2) 0.331(2) 0.017(6) Uiso 1 1 d
H8 H 0.366(3) -0.301(3) -0.092(3) 0.029(7) Uiso 1 1 d
H9 H 0.507(3) -0.340(3) -0.024(3) 0.028(7) Uiso 1 1 d
H10 H 0.369(3) -0.385(3) 0.000(3) 0.033(8) Uiso 1 1 d
H11 H 0.223(4) -0.166(3) -0.003(3) 0.037(8) Uiso 1 1 d
H12 H 0.234(3) -0.256(2) 0.085(2) 0.020(6) Uiso 1 1 d
H13 H 0.274(3) -0.124(3) 0.114(2) 0.026(7) Uiso 1 1 d
H14 H 0.904(4) 0.032(4) 0.381(4) 0.060(11) Uiso 1 1 d
H15 H 0.963(3) 0.154(3) 0.346(2) 0.029(7) Uiso 1 1 d
H16 H 0.948(4) 0.137(3) 0.466(3) 0.046(9) Uiso 1 1 d
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'
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
C13 O19 C14 119.12(14)
C15 O20 C14 119.18(16)
C8 O23 C18 116.98(16)
C2 C1 C9 119.38(19)
C2 C1 C11 117.33(18)
C9 C1 C11 123.23(17)
C1 C2 C3 120.86(19)
C4 C3 C2 120.66(18)
C3 C4 C10 120.91(19)
C6 C5 C10 120.09(19)
C5 C6 C7 120.97(19)
C8 C7 C6 119.7(2)
O23 C8 C7 123.59(19)
O23 C8 C9 115.01(17)
C7 C8 C9 121.39(18)
C8 C9 C1 122.90(18)
C8 C9 C10 117.79(18)
C1 C9 C10 119.24(18)
C5 C10 C4 121.0(2)
C5 C10 C9 120.05(18)
C4 C10 C9 118.92(19)
C12 C11 C1 124.30(18)
C11 C12 C15 124.27(17)
C11 C12 C13 119.24(18)
C15 C12 C13 116.39(17)
O21 C13 O19 118.98(18)
O21 C13 C12 125.55(19)
O19 C13 C12 115.47(17)
O20 C14 O19 109.44(15)
O20 C14 C16 105.59(17)
O19 C14 C16 105.66(16)
O20 C14 C17 111.07(17)
O19 C14 C17 110.83(17)
C16 C14 C17 113.96(17)
O22 C15 O20 118.77(18)
O22 C15 C12 125.70(18)
O20 C15 C12 115.28(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O19 C13 1.364(2)
O19 C14 1.448(2)
O20 C15 1.366(2)
O20 C14 1.440(3)
O21 C13 1.198(3)
O22 C15 1.197(2)
O23 C8 1.366(2)
O23 C18 1.435(3)
C1 C2 1.386(3)
C1 C9 1.428(3)
C1 C11 1.481(3)
C2 C3 1.409(3)
C3 C4 1.359(3)
C4 C10 1.418(3)
C5 C6 1.372(3)
C5 C10 1.417(3)
C6 C7 1.415(3)
C7 C8 1.378(3)
C8 C9 1.425(3)
C9 C10 1.429(3)
C11 C12 1.343(3)
C12 C15 1.483(3)
C12 C13 1.487(3)
C14 C16 1.503(3)
C14 C17 1.518(3)
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
C9 C1 C2 C3 -0.9(3)
C11 C1 C2 C3 176.26(18)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C10 0.9(3)
C10 C5 C6 C7 1.7(3)
C5 C6 C7 C8 -1.2(3)
C18 O23 C8 C7 -17.6(3)
C18 O23 C8 C9 161.15(18)
C6 C7 C8 O23 178.90(18)
C6 C7 C8 C9 0.2(3)
O23 C8 C9 C1 -1.5(3)
C7 C8 C9 C1 177.31(19)
O23 C8 C9 C10 -178.56(17)
C7 C8 C9 C10 0.2(3)
C2 C1 C9 C8 -176.86(18)
C11 C1 C9 C8 6.1(3)
C2 C1 C9 C10 0.2(3)
C11 C1 C9 C10 -176.84(17)
C6 C5 C10 C4 -179.14(19)
C6 C5 C10 C9 -1.2(3)
C3 C4 C10 C5 176.39(19)
C3 C4 C10 C9 -1.6(3)
C8 C9 C10 C5 0.2(3)
C1 C9 C10 C5 -176.96(19)
C8 C9 C10 C4 178.24(17)
C1 C9 C10 C4 1.0(3)
C2 C1 C11 C12 55.9(3)
C9 C1 C11 C12 -127.0(2)
C1 C11 C12 C15 14.9(3)
C1 C11 C12 C13 -168.81(18)
C14 O19 C13 O21 170.47(18)
C14 O19 C13 C12 -10.4(2)
C11 C12 C13 O21 -24.9(3)
C15 C12 C13 O21 151.65(19)
C11 C12 C13 O19 156.01(17)
C15 C12 C13 O19 -27.4(3)
C15 O20 C14 O19 -48.9(2)
C15 O20 C14 C16 -162.19(16)
C15 O20 C14 C17 73.8(2)
C13 O19 C14 O20 47.3(2)
C13 O19 C14 C16 160.59(17)
C13 O19 C14 C17 -75.5(2)
C14 O20 C15 O22 -172.33(17)
C14 O20 C15 C12 13.1(2)
C11 C12 C15 O22 28.4(3)
C13 C12 C15 O22 -148.01(19)
C11 C12 C15 O20 -157.52(18)
C13 C12 C15 O20 26.1(2)
