#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225293.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_2225293
loop_
_publ_author_name
'Hijikata, Daichi'
'Nakaema, Kosuke'
'Watanabe, Shoji'
'Okamoto, Akiko'
'Yonezawa, Noriyuki'
_publ_section_title
;
 Methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate
;
_journal_coeditor_code           IS2518
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o554
_journal_paper_doi               10.1107/S160053681000382X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H18 O5'
_chemical_formula_moiety         'C21 H18 O5'
_chemical_formula_sum            'C21 H18 O5'
_chemical_formula_weight         350.35
_chemical_melting_point_gt       427.6
_chemical_melting_point_lt       430.1
_chemical_name_systematic
;
Methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.525(2)
_cell_angle_beta                 97.919(2)
_cell_angle_gamma                106.630(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7714(2)
_cell_length_b                   9.5195(3)
_cell_length_c                   12.2737(4)
_cell_measurement_reflns_used    10631
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.7
_cell_volume                     847.73(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15482
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.0056(9)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0370
_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)+(0.0674P)²+0.1365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                2571
_reflns_number_total             3066
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2518.cif
_cod_data_source_block           I
_cod_database_code               2225293
_cod_database_fobs_code          2225293
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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_disorder_assembly
_atom_site_disorder_group
O O1 1.18952(13) 0.98013(12) 0.33288(8) 0.0454(3) Uani d . 1 . .
O O2 0.76893(17) 0.46407(13) 0.65183(9) 0.0570(3) Uani d . 1 . .
O O3 0.59054(13) 0.32936(11) 0.49174(8) 0.0423(3) Uani d . 1 . .
O O4 0.76938(14) 1.00486(13) 0.26247(8) 0.0470(3) Uani d . 1 . .
O O5 1.29922(14) 0.59184(12) 0.00036(9) 0.0479(3) Uani d . 1 . .
C C1 0.94439(17) 0.87694(14) 0.17801(11) 0.0320(3) Uani d . 1 . .
C C2 0.80587(18) 0.93926(15) 0.16515(12) 0.0363(3) Uani d . 1 . .
C C3 0.7095(2) 0.93512(17) 0.05840(12) 0.0420(4) Uani d . 1 . .
H H3 0.6144 0.9794 0.0502 0.050 Uiso calc R 1 . .
C C4 0.7548(2) 0.86624(17) -0.03362(12) 0.0431(4) Uani d . 1 . .
H H4 0.6898 0.8635 -0.1058 0.052 Uiso calc R 1 . .
C C5 0.89479(18) 0.79937(15) -0.02438(11) 0.0351(3) Uani d . 1 . .
C C6 0.9413(2) 0.72579(16) -0.11830(12) 0.0426(4) Uani d . 1 . .
H H6 0.8780 0.7228 -0.1910 0.051 Uiso calc R 1 . .
C C7 1.0735(2) 0.65969(16) -0.10717(12) 0.0439(4) Uani d . 1 . .
H H7 1.1012 0.6098 -0.1715 0.053 Uiso calc R 1 . .
C C8 1.17077(19) 0.66469(15) 0.00021(12) 0.0375(3) Uani d . 1 . .
C C9 1.13305(18) 0.73542(15) 0.09430(11) 0.0342(3) Uani d . 1 . .
H H9 1.1997 0.7383 0.1659 0.041 Uiso calc R 1 . .
C C10 0.99256(17) 0.80497(14) 0.08386(11) 0.0326(3) Uani d . 1 . .
C C11 1.04313(18) 0.88600(15) 0.29455(11) 0.0334(3) Uani d . 1 . .
C C12 0.95508(17) 0.77299(15) 0.36010(11) 0.0328(3) Uani d . 1 . .
C C13 1.00721(19) 0.79937(16) 0.47627(11) 0.0370(3) Uani d . 1 . .
H H13 1.0970 0.8899 0.5134 0.044 Uiso calc R 1 . .
C C14 0.92869(19) 0.69435(16) 0.53730(11) 0.0391(3) Uani d . 1 . .
H H14 0.9634 0.7133 0.6164 0.047 Uiso calc R 1 . .
C C15 0.79879(18) 0.56076(16) 0.48323(11) 0.0352(3) Uani d . 1 . .
C C16 0.74621(19) 0.53386(16) 0.36727(11) 0.0370(3) Uani d . 1 . .
H H16 0.6573 0.4429 0.3301 0.044 Uiso calc R 1 . .
C C17 0.82356(18) 0.63965(15) 0.30640(11) 0.0358(3) Uani d . 1 . .
H H17 0.7869 0.6214 0.2274 0.043 Uiso calc R 1 . .
C C18 0.6225(2) 1.0673(2) 0.25460(15) 0.0519(4) Uani d . 1 . .
H H18A 0.6111 1.1086 0.3297 0.062 Uiso calc R 1 . .
H H18B 0.5085 0.9895 0.2185 0.062 Uiso calc R 1 . .
H H18C 0.6472 1.1467 0.2101 0.062 Uiso calc R 1 . .
C C19 1.4033(2) 0.59325(18) 0.10659(13) 0.0460(4) Uani d . 1 . .
H H19A 1.4865 0.5344 0.0961 0.055 Uiso calc R 1 . .
H H19B 1.3203 0.5502 0.1553 0.055 Uiso calc R 1 . .
H H19C 1.4742 0.6961 0.1411 0.055 Uiso calc R 1 . .
C C20 0.72025(19) 0.44915(16) 0.55271(11) 0.0381(3) Uani d . 1 . .
C C21 0.5110(2) 0.21403(17) 0.55273(13) 0.0466(4) Uani d . 1 . .
H H21A 0.4122 0.1347 0.5020 0.056 Uiso calc R 1 . .
H H21B 0.4621 0.2568 0.6138 0.056 Uiso calc R 1 . .
H H21C 0.6051 0.1726 0.5835 0.056 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C20 O3 C21 . . 115.70(11) ?
C2 O4 C18 . . 118.25(12) ?
C8 O5 C19 . . 117.18(11) ?
C2 C1 C10 . . 120.65(12) ?
C2 C1 C11 . . 118.48(12) ?
C10 C1 C11 . . 120.86(12) ?
C1 C2 O4 . . 115.70(12) ?
C1 C2 C3 . . 121.08(14) ?
O4 C2 C3 . . 123.22(13) ?
C4 C3 C2 . . 118.99(14) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.91(13) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C4 C5 C6 . . 122.64(13) ?
C4 C5 C10 . . 118.76(13) ?
C6 C5 C10 . . 118.61(13) ?
C7 C6 C5 . . 121.56(13) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C8 . . 120.04(14) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
O5 C8 C9 . . 124.51(13) ?
O5 C8 C7 . . 114.37(12) ?
C9 C8 C7 . . 121.10(14) ?
C8 C9 C10 . . 119.48(13) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C1 C10 C5 . . 118.60(13) ?
C1 C10 C9 . . 122.18(12) ?
C5 C10 C9 . . 119.20(12) ?
O1 C11 C12 . . 121.49(12) ?
O1 C11 C1 . . 121.30(12) ?
C12 C11 C1 . . 117.20(11) ?
C17 C12 C13 . . 119.41(12) ?
C17 C12 C11 . . 120.72(11) ?
C13 C12 C11 . . 119.85(12) ?
C14 C13 C12 . . 120.21(13) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.17(12) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.85(13) ?
C14 C15 C20 . . 118.23(12) ?
C16 C15 C20 . . 121.91(12) ?
C17 C16 C15 . . 119.91(13) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C12 . . 120.43(12) ?
C16 C17 H17 . . 119.8 ?
C12 C17 H17 . . 119.8 ?
O4 C18 H18A . . 109.5 ?
O4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 C20 O3 . . 123.51(13) ?
O2 C20 C15 . . 124.10(13) ?
O3 C20 C15 . . 112.39(11) ?
O3 C21 H21A . . 109.5 ?
O3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.2154(16) ?
O2 C20 . 1.2002(17) ?
O3 C20 . 1.3368(17) ?
O3 C21 . 1.4499(17) ?
O4 C2 . 1.3772(17) ?
O4 C18 . 1.4277(18) ?
O5 C8 . 1.3687(17) ?
O5 C19 . 1.4327(18) ?
C1 C2 . 1.3708(19) ?
C1 C10 . 1.4154(19) ?
C1 C11 . 1.5065(18) ?
C2 C3 . 1.407(2) ?
C3 C4 . 1.370(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.408(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.413(2) ?
C5 C10 . 1.4231(18) ?
C6 C7 . 1.351(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.414(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3695(19) ?
C9 C10 . 1.4298(19) ?
C9 H9 . 0.9500 ?
C11 C12 . 1.4933(18) ?
C12 C17 . 1.3939(19) ?
C12 C13 . 1.3960(18) ?
C13 C14 . 1.381(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.391(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3937(19) ?
C15 C20 . 1.496(2) ?
C16 C17 . 1.3813(19) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
_geom_hbond_publ_flag
C19 H19B O2 2_766 0.98 2.57 3.461(2) 152 y
C21 H21A O1 1_445 0.98 2.49 3.4446(19) 163 y
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 O4 . . . . 179.30(11) ?
C11 C1 C2 O4 . . . . -0.32(18) ?
C10 C1 C2 C3 . . . . -0.8(2) ?
C11 C1 C2 C3 . . . . 179.60(12) ?
C18 O4 C2 C1 . . . . -177.96(12) ?
C18 O4 C2 C3 . . . . 2.1(2) ?
C1 C2 C3 C4 . . . . 0.6(2) ?
O4 C2 C3 C4 . . . . -179.50(13) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . 178.96(13) ?
C3 C4 C5 C10 . . . . -0.5(2) ?
C4 C5 C6 C7 . . . . -178.55(13) ?
C10 C5 C6 C7 . . . . 0.9(2) ?
C5 C6 C7 C8 . . . . -0.8(2) ?
C19 O5 C8 C9 . . . . -1.44(19) ?
C19 O5 C8 C7 . . . . 179.73(12) ?
C6 C7 C8 O5 . . . . 179.11(12) ?
C6 C7 C8 C9 . . . . 0.2(2) ?
O5 C8 C9 C10 . . . . -178.55(11) ?
C7 C8 C9 C10 . . . . 0.2(2) ?
C2 C1 C10 C5 . . . . 0.31(19) ?
C11 C1 C10 C5 . . . . 179.92(11) ?
C2 C1 C10 C9 . . . . -178.35(12) ?
C11 C1 C10 C9 . . . . 1.26(19) ?
C4 C5 C10 C1 . . . . 0.33(18) ?
C6 C5 C10 C1 . . . . -179.18(11) ?
C4 C5 C10 C9 . . . . 179.04(11) ?
C6 C5 C10 C9 . . . . -0.47(18) ?
C8 C9 C10 C1 . . . . 178.58(11) ?
C8 C9 C10 C5 . . . . -0.08(18) ?
C2 C1 C11 O1 . . . . -98.98(16) ?
C10 C1 C11 O1 . . . . 81.40(17) ?
C2 C1 C11 C12 . . . . 82.03(15) ?
C10 C1 C11 C12 . . . . -97.59(14) ?
O1 C11 C12 C17 . . . . -158.78(14) ?
C1 C11 C12 C17 . . . . 20.22(18) ?
O1 C11 C12 C13 . . . . 19.9(2) ?
C1 C11 C12 C13 . . . . -161.07(12) ?
C17 C12 C13 C14 . . . . -0.2(2) ?
C11 C12 C13 C14 . . . . -178.91(12) ?
C12 C13 C14 C15 . . . . 0.8(2) ?
C13 C14 C15 C16 . . . . -0.8(2) ?
C13 C14 C15 C20 . . . . 178.81(13) ?
C14 C15 C16 C17 . . . . 0.2(2) ?
C20 C15 C16 C17 . . . . -179.44(13) ?
C15 C16 C17 C12 . . . . 0.5(2) ?
C13 C12 C17 C16 . . . . -0.5(2) ?
C11 C12 C17 C16 . . . . 178.25(12) ?
C21 O3 C20 O2 . . . . -0.9(2) ?
C21 O3 C20 C15 . . . . 178.40(12) ?
C14 C15 C20 O2 . . . . -4.0(2) ?
C16 C15 C20 O2 . . . . 175.62(15) ?
C14 C15 C20 O3 . . . . 176.73(12) ?
C16 C15 C20 O3 . . . . -3.64(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744419
