#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/53/2205363.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_2205363
loop_
_publ_author_name
'Binita Suthar'
'Anthony Fowler'
'Daniel S. Jones'
'Craig A. Ogle'
_publ_section_title
;
 1-(3,4,5-Trimethoxyphenyl)naphthalene
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o607
_journal_page_last               o608
_journal_paper_doi               10.1107/S1600536805003776
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H18 O3'
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7460(10)
_cell_length_b                   12.605(4)
_cell_length_c                   18.320(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.64
_cell_measurement_theta_min      9.63
_cell_volume                     1557.8(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3231
_diffrn_reflns_theta_full        69.89
_diffrn_reflns_theta_max         69.89
_diffrn_reflns_theta_min         4.26
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 73
_diffrn_standards_interval_time  59
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.162
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.052P)²+0.0081P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1346
_reflns_number_total             1722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6164.cif
_cod_data_source_block           I
_cod_database_code               2205363
_cod_database_fobs_code          2205363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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_type_symbol
O3 0.9930(3) 0.80028(12) 0.08473(10) 0.0514(5) Uani d . 1 O
O2 1.1929(3) 0.72291(14) 0.20023(10) 0.0559(5) Uani d . 1 O
C15 0.9720(4) 0.69387(16) 0.09928(12) 0.0399(5) Uani d . 1 C
C14 1.0838(4) 0.65578(18) 0.15681(12) 0.0407(5) Uani d . 1 C
O1 1.1887(3) 0.51775(13) 0.23173(10) 0.0583(5) Uani d . 1 O
C9 0.7080(4) 0.42646(17) -0.03291(14) 0.0418(5) Uani d . 1 C
C13 1.0704(4) 0.54863(19) 0.17542(13) 0.0433(6) Uani d . 1 C
C11 0.8311(4) 0.52062(17) 0.08090(12) 0.0425(5) Uani d . 1 C
C16 0.8479(4) 0.62720(18) 0.06015(13) 0.0428(6) Uani d . 1 C
H16 0.7766 0.653 0.0205 0.051 Uiso calc R 1 H
C12 0.9422(4) 0.48290(18) 0.13849(13) 0.0463(6) Uani d . 1 C
H12 0.9303 0.4123 0.1525 0.056 Uiso calc R 1 H
C1 0.6858(4) 0.45215(16) 0.04198(13) 0.0437(6) Uani d . 1 C
C7 0.8976(6) 0.4256(2) -0.14535(16) 0.0686(8) Uani d . 1 C
H7 1.013 0.4417 -0.1709 0.082 Uiso calc R 1 H
C3 0.3724(5) 0.3583(2) 0.0422(2) 0.0679(9) Uani d . 1 C
H3 0.2624 0.3348 0.0682 0.081 Uiso calc R 1 H
C2 0.5215(5) 0.4167(2) 0.07811(17) 0.0598(7) Uani d . 1 C
H2 0.5077 0.4314 0.1276 0.072 Uiso calc R 1 H
C4 0.3879(4) 0.3363(2) -0.02890(19) 0.0629(8) Uani d . 1 C
H4 0.2876 0.2985 -0.052 0.076 Uiso calc R 1 H
C10 0.5545(4) 0.36963(18) -0.06943(16) 0.0505(7) Uani d . 1 C
C6 0.7405(6) 0.3741(3) -0.18079(18) 0.0725(9) Uani d . 1 C
H6 0.7507 0.3584 -0.2302 0.087 Uiso calc R 1 H
C19 0.8498(5) 0.84795(19) 0.03828(16) 0.0579(7) Uani d . 1 C
H19A 0.8697 0.8239 -0.0109 0.087 Uiso calc R 1 H
H19B 0.8637 0.9237 0.0401 0.087 Uiso calc R 1 H
H19C 0.7192 0.8285 0.0542 0.087 Uiso calc R 1 H
C8 0.8811(5) 0.4523(2) -0.07317(15) 0.0544(6) Uani d . 1 C
H8 0.9846 0.4879 -0.0502 0.065 Uiso calc R 1 H
C17 1.1475(6) 0.4172(2) 0.26410(19) 0.0814(11) Uani d . 1 C
H17A 1.0082 0.4119 0.2742 0.122 Uiso calc R 1 H
H17B 1.2209 0.4104 0.3087 0.122 Uiso calc R 1 H
H17C 1.1856 0.3617 0.2311 0.122 Uiso calc R 1 H
C5 0.5752(5) 0.3472(2) -0.14412(17) 0.0647(8) Uani d . 1 C
H5 0.4728 0.313 -0.1687 0.078 Uiso calc R 1 H
C18 1.3839(6) 0.7457(4) 0.1759(2) 0.0950(13) Uani d . 1 C
H18A 1.4505 0.6808 0.1635 0.142 Uiso calc R 1 H
H18B 1.4559 0.7813 0.2139 0.142 Uiso calc R 1 H
H18C 1.3769 0.7905 0.1337 0.142 Uiso calc R 1 H
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 3 2
0 4 2
-1 2 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 O3 C19 117.30(19)
C14 O2 C18 115.9(2)
O3 C15 C14 115.5(2)
O3 C15 C16 123.6(2)
C14 C15 C16 120.89(19)
O2 C14 C15 121.3(2)
O2 C14 C13 119.2(2)
C15 C14 C13 119.2(2)
C13 O1 C17 117.1(2)
C1 C9 C8 122.5(2)
C1 C9 C10 119.5(2)
C8 C9 C10 118.0(2)
O1 C13 C12 124.7(2)
O1 C13 C14 115.1(2)
C12 C13 C14 120.2(2)
C12 C11 C16 119.6(2)
C12 C11 C1 121.6(2)
C16 C11 C1 118.7(2)
C15 C16 C11 119.4(2)
C15 C16 H16 120.3
C11 C16 H16 120.3
C13 C12 C11 120.7(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C2 C1 C9 118.7(2)
C2 C1 C11 119.5(2)
C9 C1 C11 121.8(2)
C8 C7 C6 119.9(3)
C8 C7 H7 120
C6 C7 H7 120
C4 C3 C2 120.5(3)
C4 C3 H3 119.8
C2 C3 H3 119.8
C1 C2 C3 121.6(3)
C1 C2 H2 119.2
C3 C2 H2 119.2
C3 C4 C10 120.9(3)
C3 C4 H4 119.5
C10 C4 H4 119.5
C5 C10 C4 122.1(3)
C5 C10 C9 119.1(3)
C4 C10 C9 118.7(3)
C5 C6 C7 120.8(3)
C5 C6 H6 119.6
C7 C6 H6 119.6
O3 C19 H19A 109.5
O3 C19 H19B 109.5
H19A C19 H19B 109.5
O3 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C7 C8 C9 120.8(3)
C7 C8 H8 119.6
C9 C8 H8 119.6
O1 C17 H17A 109.5
O1 C17 H17B 109.5
H17A C17 H17B 109.5
O1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C6 C5 C10 121.2(3)
C6 C5 H5 119.4
C10 C5 H5 119.4
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
O3 C15 1.375(3)
O3 C19 1.421(3)
O2 C14 1.375(3)
O2 C18 1.393(4)
C15 C14 1.382(3)
C15 C16 1.386(3)
C14 C13 1.396(3)
O1 C13 1.361(3)
O1 C17 1.427(3)
C9 C1 1.418(4)
C9 C8 1.419(4)
C9 C10 1.425(3)
C13 C12 1.376(3)
C11 C12 1.379(3)
C11 C16 1.401(3)
C11 C1 1.488(3)
C16 H16 0.93
C12 H12 0.93
C1 C2 1.366(4)
C7 C8 1.369(4)
C7 C6 1.402(5)
C7 H7 0.93
C3 C4 1.336(5)
C3 C2 1.409(4)
C3 H3 0.93
C2 H2 0.93
C4 C10 1.411(4)
C4 H4 0.93
C10 C5 1.404(4)
C6 C5 1.345(5)
C6 H6 0.93
C19 H19A 0.96
C19 H19B 0.96
C19 H19C 0.96
C8 H8 0.93
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
C5 H5 0.93
C18 H18A 0.96
C18 H18B 0.96
C18 H18C 0.96
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129804
