#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226850.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_2226850
loop_
_publ_author_name
'Ali, Qamar'
'Anis, Itrat'
'VanDerveer, Donald'
'Shah, Muhammad Raza'
_publ_section_title
;
 Diethyl 2,2'-(biphenyl-2,2'-diyldioxy)diacetate
;
_journal_coeditor_code           EZ2221
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1984
_journal_paper_doi               10.1107/S1600536810026863
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H22 O6'
_chemical_formula_moiety         'C20 H22 O6'
_chemical_formula_sum            'C20 H22 O6'
_chemical_formula_weight         358.38
_chemical_name_systematic
;
Diethyl 2,2'-(biphenyl-2,2'-diyldioxy)diacetate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.733(17)
_cell_angle_beta                 95.05(2)
_cell_angle_gamma                106.897(14)
_cell_formula_units_Z            2
_cell_length_a                   7.4683(13)
_cell_length_b                   10.8189(15)
_cell_length_c                   12.050(2)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.3413
_cell_measurement_theta_min      3.0882
_cell_volume                     887.1(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_measurement_device_type  'Rigaku AFC-8S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6640
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(REQAB; Jacobson, 1998)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0394
_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)+(0.0493P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2787
_reflns_number_total             3104
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ez2221.cif
_cod_data_source_block           I
_cod_database_code               2226850
_cod_database_fobs_code          2226850
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 0.26152(13) 0.49153(10) -0.09823(8) 0.0281(2) Uani d . 1 . .
O O2 0.10844(14) 0.63977(10) -0.03410(9) 0.0289(3) Uani d . 1 . .
O O3 0.37964(13) 0.73993(9) 0.17431(8) 0.0229(2) Uani d . 1 . .
O O4 0.64269(14) 1.13019(10) 0.42800(8) 0.0270(2) Uani d . 1 . .
O O5 0.71807(19) 1.39716(12) 0.43450(10) 0.0455(3) Uani d . 1 . .
O O6 0.74896(14) 1.45726(9) 0.62997(8) 0.0284(2) Uani d . 1 . .
C C1 0.2426(2) 0.36891(16) -0.29568(13) 0.0315(3) Uani d . 1 . .
H H1A 0.1754 0.3436 -0.3759 0.047 Uiso calc R 1 . .
H H1B 0.2329 0.2872 -0.2723 0.047 Uiso calc R 1 . .
H H1C 0.3768 0.4191 -0.2912 0.047 Uiso calc R 1 . .
C C2 0.1555(2) 0.45549(19) -0.21611(13) 0.0407(4) Uani d . 1 . .
H H2A 0.1631 0.5380 -0.2395 0.049 Uiso calc R 1 . .
H H2B 0.0201 0.4056 -0.2194 0.049 Uiso calc R 1 . .
C C3 0.22147(18) 0.58407(13) -0.01637(12) 0.0213(3) Uani d . 1 . .
C C4 0.33426(18) 0.60535(13) 0.10190(11) 0.0218(3) Uani d . 1 . .
H H4A 0.2593 0.5424 0.1406 0.026 Uiso calc R 1 . .
H H4B 0.4532 0.5843 0.0911 0.026 Uiso calc R 1 . .
C C5 0.50568(17) 0.83979(13) 0.14036(11) 0.0197(3) Uani d . 1 . .
C C6 0.51573(18) 0.97228(13) 0.19636(11) 0.0196(3) Uani d . 1 . .
C C7 0.64460(19) 1.07739(13) 0.16831(12) 0.0239(3) Uani d . 1 . .
H H7A 0.6553 1.1682 0.2068 0.029 Uiso calc R 1 . .
C C8 0.75716(19) 1.05198(14) 0.08549(12) 0.0261(3) Uani d . 1 . .
H H8A 0.8428 1.1247 0.0667 0.031 Uiso calc R 1 . .
C C9 0.74388(19) 0.92018(15) 0.03053(12) 0.0267(3) Uani d . 1 . .
H H9A 0.8203 0.9023 -0.0266 0.032 Uiso calc R 1 . .
C C10 0.61985(19) 0.81358(14) 0.05811(12) 0.0244(3) Uani d . 1 . .
H H10A 0.6129 0.7232 0.0210 0.029 Uiso calc R 1 . .
C C11 0.38246(18) 1.00240(13) 0.27616(11) 0.0207(3) Uani d . 1 . .
C C12 0.18639(19) 0.95132(13) 0.23529(12) 0.0242(3) Uani d . 1 . .
H H12A 0.1391 0.8899 0.1593 0.029 Uiso calc R 1 . .
C C13 0.0593(2) 0.98855(14) 0.30363(13) 0.0277(3) Uani d . 1 . .
H H13A -0.0734 0.9537 0.2745 0.033 Uiso calc R 1 . .
C C14 0.1289(2) 1.07714(14) 0.41479(13) 0.0297(3) Uani d . 1 . .
H H14A 0.0430 1.1041 0.4615 0.036 Uiso calc R 1 . .
C C15 0.3225(2) 1.12712(14) 0.45896(13) 0.0281(3) Uani d . 1 . .
H H15A 0.3685 1.1868 0.5358 0.034 Uiso calc R 1 . .
C C16 0.44882(19) 1.08923(13) 0.39009(12) 0.0223(3) Uani d . 1 . .
C C17 0.7184(2) 1.23201(14) 0.53605(12) 0.0284(3) Uani d . 1 . .
H H17A 0.8479 1.2336 0.5641 0.034 Uiso calc R 1 . .
H H17B 0.6384 1.2107 0.5943 0.034 Uiso calc R 1 . .
C C18 0.72672(19) 1.36982(14) 0.52501(12) 0.0263(3) Uani d . 1 . .
C C19 0.7734(2) 1.59703(14) 0.63189(14) 0.0349(4) Uani d . 1 . .
H H19A 0.6748 1.5994 0.5726 0.042 Uiso calc R 1 . .
H H19B 0.8998 1.6391 0.6141 0.042 Uiso calc R 1 . .
C C20 0.7560(2) 1.67243(15) 0.75077(14) 0.0352(4) Uani d . 1 . .
H H20A 0.7719 1.7665 0.7541 0.053 Uiso calc R 1 . .
H H20B 0.8544 1.6699 0.8088 0.053 Uiso calc R 1 . .
H H20C 0.6303 1.6303 0.7674 0.053 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 0.0033 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
_geom_angle_publ_flag
C3 O1 C2 . . 116.34(11) ?
C5 O3 C4 . . 116.66(10) ?
C16 O4 C17 . . 117.43(11) ?
C18 O6 C19 . . 115.91(11) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C1 . . 107.38(12) ?
O1 C2 H2A . . 110.2 ?
C1 C2 H2A . . 110.2 ?
O1 C2 H2B . . 110.2 ?
C1 C2 H2B . . 110.2 ?
H2A C2 H2B . . 108.5 ?
O2 C3 O1 . . 124.57(13) ?
O2 C3 C4 . . 125.14(12) ?
O1 C3 C4 . . 110.27(11) ?
O3 C4 C3 . . 111.80(11) ?
O3 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
O3 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 107.9 ?
O3 C5 C10 . . 123.59(12) ?
O3 C5 C6 . . 115.63(11) ?
C10 C5 C6 . . 120.77(12) ?
C7 C6 C5 . . 118.18(12) ?
C7 C6 C11 . . 119.86(12) ?
C5 C6 C11 . . 121.75(12) ?
C8 C7 C6 . . 121.36(13) ?
C8 C7 H7A . . 119.3 ?
C6 C7 H7A . . 119.3 ?
C9 C8 C7 . . 119.49(13) ?
C9 C8 H8A . . 120.3 ?
C7 C8 H8A . . 120.3 ?
C8 C9 C10 . . 120.55(13) ?
C8 C9 H9A . . 119.7 ?
C10 C9 H9A . . 119.7 ?
C9 C10 C5 . . 119.64(13) ?
C9 C10 H10A . . 120.2 ?
C5 C10 H10A . . 120.2 ?
C12 C11 C16 . . 118.38(12) ?
C12 C11 C6 . . 119.93(12) ?
C16 C11 C6 . . 121.54(12) ?
C13 C12 C11 . . 121.36(13) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C14 C13 C12 . . 119.08(13) ?
C14 C13 H13A . . 120.5 ?
C12 C13 H13A . . 120.5 ?
C13 C14 C15 . . 120.95(13) ?
C13 C14 H14A . . 119.5 ?
C15 C14 H14A . . 119.5 ?
C14 C15 C16 . . 119.63(14) ?
C14 C15 H15A . . 120.2 ?
C16 C15 H15A . . 120.2 ?
O4 C16 C15 . . 123.64(12) ?
O4 C16 C11 . . 115.79(12) ?
C15 C16 C11 . . 120.56(13) ?
O4 C17 C18 . . 111.40(12) ?
O4 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
O4 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 108.0 ?
O5 C18 O6 . . 124.81(13) ?
O5 C18 C17 . . 124.61(13) ?
O6 C18 C17 . . 110.57(12) ?
O6 C19 C20 . . 108.07(12) ?
O6 C19 H19A . . 110.1 ?
C20 C19 H19A . . 110.1 ?
O6 C19 H19B . . 110.1 ?
C20 C19 H19B . . 110.1 ?
H19A C19 H19B . . 108.4 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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 C3 . 1.3374(16) ?
O1 C2 . 1.4618(18) ?
O2 C3 . 1.2044(16) ?
O3 C5 . 1.3864(16) ?
O3 C4 . 1.4181(16) ?
O4 C16 . 1.3816(17) ?
O4 C17 . 1.4167(17) ?
O5 C18 . 1.2017(18) ?
O6 C18 . 1.3362(17) ?
O6 C19 . 1.4634(17) ?
C1 C2 . 1.492(2) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5175(19) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C10 . 1.3916(18) ?
C5 C6 . 1.3971(18) ?
C6 C7 . 1.3966(19) ?
C6 C11 . 1.4897(18) ?
C7 C8 . 1.386(2) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.381(2) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.388(2) ?
C9 H9A . 0.9500 ?
C10 H10A . 0.9500 ?
C11 C12 . 1.399(2) ?
C11 C16 . 1.402(2) ?
C12 C13 . 1.3900(19) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.385(2) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.389(2) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.3913(19) ?
C15 H15A . 0.9500 ?
C17 C18 . 1.514(2) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C19 C20 . 1.495(2) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 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
C4 H4b O1 2_665 0.99 2.50 3.472(2) 167.70(10)
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
C3 O1 C2 C1 . . . . 171.24(12) ?
C2 O1 C3 O2 . . . . -1.3(2) ?
C2 O1 C3 C4 . . . . 176.98(12) ?
C5 O3 C4 C3 . . . . -67.26(14) ?
O2 C3 C4 O3 . . . . -33.27(18) ?
O1 C3 C4 O3 . . . . 148.41(11) ?
C4 O3 C5 C10 . . . . -15.26(18) ?
C4 O3 C5 C6 . . . . 166.12(11) ?
O3 C5 C6 C7 . . . . 178.06(11) ?
C10 C5 C6 C7 . . . . -0.60(19) ?
O3 C5 C6 C11 . . . . -7.26(18) ?
C10 C5 C6 C11 . . . . 174.08(12) ?
C5 C6 C7 C8 . . . . 1.4(2) ?
C11 C6 C7 C8 . . . . -173.42(12) ?
C6 C7 C8 C9 . . . . -0.9(2) ?
C7 C8 C9 C10 . . . . -0.4(2) ?
C8 C9 C10 C5 . . . . 1.1(2) ?
O3 C5 C10 C9 . . . . -179.17(12) ?
C6 C5 C10 C9 . . . . -0.6(2) ?
C7 C6 C11 C12 . . . . 116.47(14) ?
C5 C6 C11 C12 . . . . -58.13(18) ?
C7 C6 C11 C16 . . . . -58.95(18) ?
C5 C6 C11 C16 . . . . 126.46(14) ?
C16 C11 C12 C13 . . . . 2.17(19) ?
C6 C11 C12 C13 . . . . -173.39(12) ?
C11 C12 C13 C14 . . . . -0.6(2) ?
C12 C13 C14 C15 . . . . -1.0(2) ?
C13 C14 C15 C16 . . . . 0.9(2) ?
C17 O4 C16 C15 . . . . -9.89(19) ?
C17 O4 C16 C11 . . . . 171.55(11) ?
C14 C15 C16 O4 . . . . -177.75(12) ?
C14 C15 C16 C11 . . . . 0.8(2) ?
C12 C11 C16 O4 . . . . 176.37(11) ?
C6 C11 C16 O4 . . . . -8.15(18) ?
C12 C11 C16 C15 . . . . -2.24(19) ?
C6 C11 C16 C15 . . . . 173.24(12) ?
C16 O4 C17 C18 . . . . -75.23(15) ?
C19 O6 C18 O5 . . . . -3.1(2) ?
C19 O6 C18 C17 . . . . 175.61(12) ?
O4 C17 C18 O5 . . . . -17.8(2) ?
O4 C17 C18 O6 . . . . 163.46(11) ?
C18 O6 C19 C20 . . . . 168.59(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745514
