#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/76/2237692.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_2237692
loop_
_publ_author_name
'Sakamoto, Rei'
'Hijikata, Daichi'
'Isozaki, Katsuhiro'
'Yonezawa, Noriyuki'
'Okamoto, Akiko'
_publ_section_title
;
 Bis(1-benzoyl-7-methoxynaphthalen-2-yl) terephthalate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o557
_journal_paper_doi               10.1107/S1600536813007186
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C44 H30 O8'
_chemical_formula_moiety         'C44 H30 O8'
_chemical_formula_sum            'C44 H30 O8'
_chemical_formula_weight         686.72
_chemical_name_systematic
;
Bis(1-benzoyl-7-methoxynaphthalen-2-yl) terephthalate
;
_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                 106.610(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.977(5)
_cell_length_b                   14.922(7)
_cell_length_c                   11.709(6)
_cell_measurement_reflns_used    4873
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.13
_cell_volume                     1670.5(14)
_computing_cell_refinement       'CrystalClear (Rigaku, 2006)'
_computing_data_collection       'CrystalClear (Rigaku, 2006)'
_computing_data_reduction        'CrystalClear (Rigaku, 2006)'
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0435
_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)+(0.0716P)²+0.0599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2354
_reflns_number_total             2909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rn2113.cif
_cod_data_source_block           I
_cod_database_code               2237692
_cod_database_fobs_code          2237692
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 0.89735(14) 0.10507(8) 0.99483(11) 0.0365(3) Uani d . 1 1
O O2 0.58268(14) 0.02769(9) 1.24046(11) 0.0370(4) Uani d . 1 1
O O3 0.88903(12) -0.06534(8) 0.75583(10) 0.0274(3) Uani d . 1 1
O O4 0.71518(13) -0.10741(8) 0.59275(11) 0.0331(3) Uani d . 1 1
C C1 0.78482(18) -0.02789(11) 0.90842(14) 0.0250(4) Uani d . 1 1
C C2 0.81191(18) -0.09200(11) 0.83329(15) 0.0268(4) Uani d . 1 1
C C3 0.78049(19) -0.18316(12) 0.83991(16) 0.0300(4) Uani d . 1 1
H H3 0.8021 -0.2253 0.7870 0.036 Uiso calc R 1 1
C C4 0.71849(19) -0.20981(12) 0.92361(16) 0.0317(4) Uani d . 1 1
H H4 0.6966 -0.2714 0.9288 0.038 Uiso calc R 1 1
C C5 0.6193(2) -0.17586(12) 1.08887(16) 0.0323(4) Uani d . 1 1
H H5 0.5964 -0.2373 1.0932 0.039 Uiso calc R 1 1
C C6 0.58792(19) -0.11631(12) 1.16488(16) 0.0328(4) Uani d . 1 1
H H6 0.5437 -0.1363 1.2221 0.039 Uiso calc R 1 1
C C7 0.62077(19) -0.02485(12) 1.15912(15) 0.0298(4) Uani d . 1 1
C C8 0.68635(18) 0.00528(12) 1.07862(14) 0.0268(4) Uani d . 1 1
H H8 0.7093 0.0670 1.0768 0.032 Uiso calc R 1 1
C C9 0.72028(18) -0.05563(11) 0.99763(15) 0.0263(4) Uani d . 1 1
C C10 0.68584(18) -0.14785(11) 1.00309(15) 0.0286(4) Uani d . 1 1
C C11 0.83238(18) 0.06688(11) 0.90305(15) 0.0273(4) Uani d . 1 1
C C12 0.79951(18) 0.11478(11) 0.78599(15) 0.0272(4) Uani d . 1 1
C C13 0.68449(19) 0.09267(11) 0.69170(16) 0.0295(4) Uani d . 1 1
H H13 0.6248 0.0451 0.7002 0.035 Uiso calc R 1 1
C C14 0.6557(2) 0.13957(12) 0.58465(17) 0.0366(5) Uani d . 1 1
H H14 0.5757 0.1250 0.5208 0.044 Uiso calc R 1 1
C C15 0.7446(2) 0.20763(13) 0.57206(18) 0.0426(5) Uani d . 1 1
H H15 0.7262 0.2393 0.4988 0.051 Uiso calc R 1 1
C C16 0.8603(2) 0.22994(13) 0.66549(19) 0.0425(5) Uani d . 1 1
H H16 0.9210 0.2765 0.6558 0.051 Uiso calc R 1 1
C C17 0.8877(2) 0.18470(12) 0.77284(18) 0.0365(5) Uani d . 1 1
H H17 0.9660 0.2010 0.8374 0.044 Uiso calc R 1 1
C C18 0.6184(2) 0.12025(13) 1.24527(18) 0.0409(5) Uani d . 1 1
H H18A 0.5809 0.1469 1.1661 0.049 Uiso calc R 1 1
H H18B 0.7204 0.1267 1.2711 0.049 Uiso calc R 1 1
H H18C 0.5784 0.1509 1.3020 0.049 Uiso calc R 1 1
C C19 0.82851(18) -0.07386(11) 0.63596(15) 0.0259(4) Uani d . 1 1
C C20 0.91934(18) -0.03603(11) 0.56745(15) 0.0256(4) Uani d . 1 1
C C21 0.87490(19) -0.04257(12) 0.44403(16) 0.0306(4) Uani d . 1 1
H H21 0.7890 -0.0716 0.4059 0.037 Uiso calc R 1 1
C C22 1.04521(19) 0.00720(12) 0.62350(15) 0.0316(4) Uani d . 1 1
H H22 1.0756 0.0122 0.7079 0.038 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_site_symmetry_1
_geom_angle
C7 O2 C18 . 117.86(14)
C19 O3 C2 . 118.32(13)
C2 C1 C9 . 118.35(15)
C2 C1 C11 . 120.41(15)
C9 C1 C11 . 121.05(15)
C1 C2 C3 . 123.39(16)
C1 C2 O3 . 117.35(15)
C3 C2 O3 . 118.86(15)
C4 C3 C2 . 118.58(16)
C4 C3 H3 . 120.7
C2 C3 H3 . 120.7
C3 C4 C10 . 121.40(17)
C3 C4 H4 . 119.3
C10 C4 H4 . 119.3
C6 C5 C10 . 121.01(17)
C6 C5 H5 . 119.5
C10 C5 H5 . 119.5
C5 C6 C7 . 120.15(16)
C5 C6 H6 . 119.9
C7 C6 H6 . 119.9
O2 C7 C8 . 125.02(17)
O2 C7 C6 . 114.00(15)
C8 C7 C6 . 120.98(16)
C7 C8 C9 . 120.07(17)
C7 C8 H8 . 120.0
C9 C8 H8 . 120.0
C8 C9 C10 . 118.76(15)
C8 C9 C1 . 122.84(16)
C10 C9 C1 . 118.38(15)
C4 C10 C5 . 121.11(16)
C4 C10 C9 . 119.88(16)
C5 C10 C9 . 119.02(16)
O1 C11 C12 . 120.23(16)
O1 C11 C1 . 119.77(16)
C12 C11 C1 . 120.00(15)
C13 C12 C17 . 119.52(17)
C13 C12 C11 . 122.05(16)
C17 C12 C11 . 118.43(16)
C12 C13 C14 . 120.55(17)
C12 C13 H13 . 119.7
C14 C13 H13 . 119.7
C15 C14 C13 . 119.44(18)
C15 C14 H14 . 120.3
C13 C14 H14 . 120.3
C14 C15 C16 . 120.47(18)
C14 C15 H15 . 119.8
C16 C15 H15 . 119.8
C17 C16 C15 . 120.28(19)
C17 C16 H16 . 119.9
C15 C16 H16 . 119.9
C16 C17 C12 . 119.72(19)
C16 C17 H17 . 120.1
C12 C17 H17 . 120.1
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
O4 C19 O3 . 123.71(16)
O4 C19 C20 . 125.10(16)
O3 C19 C20 . 111.19(14)
C21 C20 C22 . 119.86(16)
C21 C20 C19 . 118.26(16)
C22 C20 C19 . 121.86(16)
C22 C21 C20 3_756 120.34(17)
C22 C21 H21 3_756 119.8
C20 C21 H21 . 119.8
C21 C22 C20 3_756 119.80(17)
C21 C22 H22 3_756 120.1
C20 C22 H22 . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C11 . 1.225(2)
O2 C7 . 1.369(2)
O2 C18 . 1.423(2)
O3 C19 . 1.366(2)
O3 C2 . 1.404(2)
O4 C19 . 1.208(2)
C1 C2 . 1.378(2)
C1 C9 . 1.436(2)
C1 C11 . 1.499(2)
C2 C3 . 1.403(3)
C3 C4 . 1.359(2)
C3 H3 . 0.9500
C4 C10 . 1.414(3)
C4 H4 . 0.9500
C5 C6 . 1.356(3)
C5 C10 . 1.416(2)
C5 H5 . 0.9500
C6 C7 . 1.410(3)
C6 H6 . 0.9500
C7 C8 . 1.368(2)
C8 C9 . 1.422(2)
C8 H8 . 0.9500
C9 C10 . 1.424(3)
C11 C12 . 1.497(2)
C12 C13 . 1.386(3)
C12 C17 . 1.401(3)
C13 C14 . 1.392(3)
C13 H13 . 0.9500
C14 C15 . 1.384(3)
C14 H14 . 0.9500
C15 C16 . 1.385(3)
C15 H15 . 0.9500
C16 C17 . 1.383(3)
C16 H16 . 0.9500
C17 H17 . 0.9500
C18 H18A . 0.9800
C18 H18B . 0.9800
C18 H18C . 0.9800
C19 C20 . 1.483(2)
C20 C21 . 1.389(3)
C20 C22 . 1.397(3)
C21 C22 3_756 1.378(3)
C21 H21 . 0.9500
C22 C21 3_756 1.378(3)
C22 H22 . 0.9500
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
C8 H8 O1 . 0.95 2.41 2.965(3) 117
C16 H16 O1 4_554 0.95 2.55 3.258(3) 132
C22 H22 O3 . 0.95 2.39 2.717(3) 100
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_site_symmetry_4
_geom_torsion
C9 C1 C2 C3 . -0.4(3)
C11 C1 C2 C3 . 174.71(16)
C9 C1 C2 O3 . -173.00(14)
C11 C1 C2 O3 . 2.1(2)
C19 O3 C2 C1 . -120.17(17)
C19 O3 C2 C3 . 66.9(2)
C1 C2 C3 C4 . 0.9(3)
O3 C2 C3 C4 . 173.35(16)
C2 C3 C4 C10 . -0.1(3)
C10 C5 C6 C7 . 0.3(3)
C18 O2 C7 C8 . -2.5(3)
C18 O2 C7 C6 . 176.79(16)
C5 C6 C7 O2 . 179.69(17)
C5 C6 C7 C8 . -1.0(3)
O2 C7 C8 C9 . -179.64(16)
C6 C7 C8 C9 . 1.1(3)
C7 C8 C9 C10 . -0.6(2)
C7 C8 C9 C1 . 177.87(16)
C2 C1 C9 C8 . -179.22(16)
C11 C1 C9 C8 . 5.7(3)
C2 C1 C9 C10 . -0.8(2)
C11 C1 C9 C10 . -175.87(15)
C3 C4 C10 C5 . 179.04(17)
C3 C4 C10 C9 . -1.1(3)
C6 C5 C10 C4 . -179.90(17)
C6 C5 C10 C9 . 0.2(3)
C8 C9 C10 C4 . -179.97(16)
C1 C9 C10 C4 . 1.5(2)
C8 C9 C10 C5 . -0.1(2)
C1 C9 C10 C5 . -178.62(16)
C2 C1 C11 O1 . -129.92(19)
C9 C1 C11 O1 . 45.1(2)
C2 C1 C11 C12 . 50.6(2)
C9 C1 C11 C12 . -134.45(17)
O1 C11 C12 C13 . -152.96(17)
C1 C11 C12 C13 . 26.6(2)
O1 C11 C12 C17 . 26.3(2)
C1 C11 C12 C17 . -154.14(16)
C17 C12 C13 C14 . -0.3(3)
C11 C12 C13 C14 . 178.96(16)
C12 C13 C14 C15 . 1.2(3)
C13 C14 C15 C16 . -0.9(3)
C14 C15 C16 C17 . -0.4(3)
C15 C16 C17 C12 . 1.3(3)
C13 C12 C17 C16 . -1.0(3)
C11 C12 C17 C16 . 179.72(17)
C2 O3 C19 O4 . -4.1(2)
C2 O3 C19 C20 . 175.43(13)
O4 C19 C20 C21 . -2.9(3)
O3 C19 C20 C21 . 177.60(14)
O4 C19 C20 C22 . 175.60(17)
O3 C19 C20 C22 . -3.9(2)
C22 C20 C21 C22 3_756 0.5(3)
C19 C20 C21 C22 3_756 179.03(16)
C21 C20 C22 C21 3_756 -0.5(3)
C19 C20 C22 C21 3_756 -178.97(16)
