#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/10/2231096.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_2231096
loop_
_publ_author_name
'Kung Pui, Law'
'Hung, Wong Woei'
'M. Yamin, Bohari'
'Kassim, Mohammad B.'
_publ_section_title
;
 3,3'',4,4''-Tetramethoxy-1,1':4',1''-terphenyl
;
_journal_coeditor_code           GK2390
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1892
_journal_paper_doi               10.1107/S1600536811025207
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H22 O4'
_chemical_formula_moiety         'C22 H22 O4'
_chemical_formula_sum            'C22 H22 O4'
_chemical_formula_weight         350.40
_chemical_melting_point_gt       576
_chemical_melting_point_lt       578
_chemical_name_systematic
;
3,3'',4,4''-Tetramethoxy-1,1':4',1''-terphenyl
;
_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                 105.476(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.217(3)
_cell_length_b                   8.808(2)
_cell_length_c                   8.058(2)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      1.60
_cell_volume                     904.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5114
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.126
_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     120
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0568
_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)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                1166
_reflns_number_total             1866
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2390.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231096
_cod_database_fobs_code          2231096
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 0.35830(11) 0.46473(15) -0.01311(17) 0.0655(5) Uani d . 1 1
O O2 0.41248(11) 0.60399(17) 0.27724(18) 0.0718(5) Uani d . 1 1
C C1 0.01164(14) 0.6080(2) 0.6254(2) 0.0588(5) Uani d . 1 1
H H1 0.0205 0.6821 0.7103 0.071 Uiso calc R 1 1
C C2 0.07975(14) 0.6046(2) 0.5231(2) 0.0576(5) Uani d . 1 1
H H2 0.1332 0.6763 0.5405 0.069 Uiso calc R 1 1
C C3 0.07065(14) 0.4961(2) 0.3938(2) 0.0521(5) Uani d . 1 1
C C4 0.14417(14) 0.4894(2) 0.2832(2) 0.0517(5) Uani d . 1 1
C C5 0.24440(15) 0.5542(2) 0.3353(2) 0.0523(5) Uani d . 1 1
H H5 0.2648 0.6042 0.4406 0.063 Uiso calc R 1 1
C C6 0.31329(14) 0.5458(2) 0.2345(2) 0.0517(5) Uani d . 1 1
C C7 0.28368(15) 0.4708(2) 0.0755(2) 0.0525(5) Uani d . 1 1
C C8 0.18531(16) 0.4092(2) 0.0216(2) 0.0626(6) Uani d . 1 1
H H8 0.1644 0.3607 -0.0845 0.075 Uiso calc R 1 1
C C9 0.11677(15) 0.4189(2) 0.1246(2) 0.0630(6) Uani d . 1 1
H H9 0.0502 0.3765 0.0856 0.076 Uiso calc R 1 1
C C10 0.44505(19) 0.6888(3) 0.4319(3) 0.0965(9) Uani d . 1 1
H H10A 0.3951 0.7680 0.4316 0.145 Uiso calc R 1 1
H H10B 0.5127 0.7329 0.4402 0.145 Uiso calc R 1 1
H H10C 0.4495 0.6230 0.5285 0.145 Uiso calc R 1 1
C C11 0.33034(18) 0.3959(3) -0.1786(2) 0.0817(7) Uani d . 1 1
H H11A 0.3120 0.2916 -0.1680 0.123 Uiso calc R 1 1
H H11B 0.3887 0.4012 -0.2282 0.123 Uiso calc R 1 1
H H11C 0.2714 0.4485 -0.2514 0.123 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_site_symmetry_3
_geom_angle
C7 O1 C11 . . 117.68(15)
C6 O2 C10 . . 117.78(15)
C2 C1 C3 . 3_566 122.27(18)
C2 C1 H1 . . 118.9
C3 C1 H1 3_566 . 118.9
C1 C2 C3 . . 121.59(18)
C1 C2 H2 . . 119.2
C3 C2 H2 . . 119.2
C2 C3 C1 . 3_566 116.14(17)
C2 C3 C4 . . 122.42(18)
C1 C3 C4 3_566 . 121.43(17)
C9 C4 C5 . . 117.06(17)
C9 C4 C3 . . 121.46(17)
C5 C4 C3 . . 121.48(17)
C6 C5 C4 . . 121.58(18)
C6 C5 H5 . . 119.2
C4 C5 H5 . . 119.2
O2 C6 C5 . . 125.06(17)
O2 C6 C7 . . 115.03(16)
C5 C6 C7 . . 119.90(17)
O1 C7 C8 . . 125.24(18)
O1 C7 C6 . . 115.63(17)
C8 C7 C6 . . 119.13(17)
C7 C8 C9 . . 120.26(18)
C7 C8 H8 . . 119.9
C9 C8 H8 . . 119.9
C4 C9 C8 . . 122.05(19)
C4 C9 H9 . . 119.0
C8 C9 H9 . . 119.0
O2 C10 H10A . . 109.5
O2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
O2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
O1 C11 H11A . . 109.5
O1 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
O1 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.364(2)
O1 C11 . 1.421(2)
O2 C6 . 1.364(2)
O2 C10 . 1.418(2)
C1 C2 . 1.373(3)
C1 C3 3_566 1.400(3)
C1 H1 . 0.9300
C2 C3 . 1.395(3)
C2 H2 . 0.9300
C3 C1 3_566 1.400(3)
C3 C4 . 1.484(3)
C4 C9 . 1.380(3)
C4 C5 . 1.400(3)
C5 C6 . 1.374(2)
C5 H5 . 0.9300
C6 C7 . 1.401(3)
C7 C8 . 1.368(3)
C8 C9 . 1.385(3)
C8 H8 . 0.9300
C9 H9 . 0.9300
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 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
_geom_hbond_publ_flag
C10 H10A O1 4_576 0.96 2.47 3.331(3) 149 yes
