#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/29/2222981.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_2222981
loop_
_publ_author_name
'Nowakowska-Bogdan, Ewa Maria'
'Wicher, Ewa'
'Ejsmont, Krzysztof'
'Zaleski, Jacek'
_publ_section_title
9-Ethoxy-1,5,13-trimethyl-8,10-dioxatetracyclo[7.7.1.0^2,7^.0^11,16^]heptadeca-2,4,6,11,13,15-hexaene
_journal_coeditor_code           BT2970
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2228
_journal_paper_doi               10.1107/S1600536809032747
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H22 O3'
_chemical_formula_moiety         'C20 H22 O3'
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.38
_chemical_name_common
;
1-ethoxy-5,8,11-trimethyldibenzo[c,d]-2,14-dioxa[3,3,1]nonane
;
_chemical_name_systematic
;9-Ethoxy-1,5,13-trimethyl-8,10-dioxatetracyclo[7.7.1.0^2,7^.0^11,16^]heptadeca-
2,4,6,11,13,15-hexaene
;
_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                 96.901(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3718(6)
_cell_length_b                   11.6446(5)
_cell_length_c                   10.2260(4)
_cell_measurement_reflns_used    2985
_cell_measurement_temperature    90.00(10)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.66
_cell_volume                     1698.96(12)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.00(10)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9989
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0472
_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)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1751
_reflns_number_total             2985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2970.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222981
_cod_database_fobs_code          2222981
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_disorder_assembly
_atom_site_disorder_group
C C1 0.24961(15) 0.47696(17) 0.2890(2) 0.0235(5) Uani d . 1 . .
O O1A 0.20501(9) 0.37104(11) 0.26845(13) 0.0263(4) Uani d . 1 . .
C C1B 0.17179(18) 0.3422(2) 0.1307(2) 0.0317(6) Uani d . 1 . .
C C1C 0.13069(17) 0.22326(18) 0.1300(2) 0.0379(6) Uani d . 1 . .
H H1C1 0.1089 0.2012 0.0411 0.057 Uiso calc R 1 . .
H H1C2 0.0791 0.2226 0.1816 0.057 Uiso calc R 1 . .
H H1C3 0.1778 0.1701 0.1668 0.057 Uiso calc R 1 . .
O O2 0.33294(10) 0.47258(12) 0.22253(13) 0.0288(4) Uani d . 1 . .
C C3 0.40517(14) 0.55031(17) 0.26325(19) 0.0226(5) Uani d . 1 . .
C C4 0.48180(15) 0.55002(18) 0.1881(2) 0.0236(5) Uani d . 1 . .
C C5 0.55726(14) 0.62572(17) 0.21702(19) 0.0236(5) Uani d . 1 . .
C C5A 0.64239(15) 0.62257(19) 0.1394(2) 0.0294(5) Uani d . 1 . .
H H51 0.6221 0.6032 0.0492 0.044 Uiso calc R 1 . .
H H52 0.6862 0.5660 0.1771 0.044 Uiso calc R 1 . .
H H53 0.6720 0.6966 0.1433 0.044 Uiso calc R 1 . .
C C6 0.55384(16) 0.70296(18) 0.3227(2) 0.0271(5) Uani d . 1 . .
C C7 0.47795(15) 0.70088(18) 0.3991(2) 0.0253(5) Uani d . 1 . .
C C7A 0.40231(14) 0.62393(17) 0.37198(18) 0.0222(5) Uani d . 1 . .
C C8 0.31708(14) 0.62109(17) 0.45321(19) 0.0218(5) Uani d . 1 . .
C C8A 0.34643(15) 0.64395(18) 0.60163(19) 0.0276(5) Uani d . 1 . .
H H81 0.2923 0.6397 0.6480 0.041 Uiso calc R 1 . .
H H82 0.3738 0.7190 0.6129 0.041 Uiso calc R 1 . .
H H83 0.3914 0.5873 0.6360 0.041 Uiso calc R 1 . .
C C9A 0.24205(14) 0.70553(17) 0.38933(19) 0.0226(5) Uani d . 1 . .
C C9 0.23106(15) 0.81749(18) 0.4337(2) 0.0256(5) Uani d . 1 . .
C C10 0.16298(15) 0.89076(19) 0.3686(2) 0.0256(5) Uani d . 1 . .
C C11 0.10309(14) 0.85430(17) 0.2566(2) 0.0244(5) Uani d . 1 . .
C C11A 0.03150(16) 0.93435(19) 0.1825(2) 0.0341(6) Uani d . 1 . .
H H111 -0.0282 0.8965 0.1681 0.051 Uiso calc R 1 . .
H H112 0.0515 0.9543 0.0992 0.051 Uiso calc R 1 . .
H H113 0.0260 1.0027 0.2334 0.051 Uiso calc R 1 . .
C C12 0.11309(15) 0.74147(18) 0.2120(2) 0.0240(5) Uani d . 1 . .
C C13 0.18201(14) 0.66987(17) 0.27796(19) 0.0225(5) Uani d . 1 . .
O O14 0.18724(10) 0.56098(11) 0.22264(13) 0.0272(4) Uani d . 1 . .
C C15 0.27228(16) 0.50062(18) 0.4352(2) 0.0240(5) Uani d . 1 . .
H H1B1 0.2258(16) 0.3455(18) 0.076(2) 0.043(7) Uiso d . 1 . .
H H1B2 0.1230(15) 0.4022(18) 0.094(2) 0.033(6) Uiso d . 1 . .
H H4A 0.4837(14) 0.4925(18) 0.116(2) 0.028(6) Uiso d . 1 . .
H H6A 0.6069(14) 0.7588(18) 0.3474(19) 0.025(5) Uiso d . 1 . .
H H7A 0.4784(14) 0.7539(18) 0.472(2) 0.027(6) Uiso d . 1 . .
H H9A 0.2729(14) 0.8461(17) 0.515(2) 0.028(6) Uiso d . 1 . .
H H10A 0.1543(14) 0.9711(18) 0.403(2) 0.031(6) Uiso d . 1 . .
H H12A 0.0748(17) 0.7141(19) 0.133(2) 0.044(7) Uiso d . 1 . .
H H15A 0.3208(15) 0.4429(19) 0.477(2) 0.035(6) Uiso d . 1 . .
H H15B 0.2132(16) 0.4963(17) 0.480(2) 0.032(6) Uiso d . 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
O1A C1 O14 . . 106.32(16) ?
O1A C1 O2 . . 106.81(16) ?
O14 C1 O2 . . 107.79(15) n
O1A C1 C15 . . 110.49(16) ?
O14 C1 C15 . . 112.89(17) ?
O2 C1 C15 . . 112.18(17) ?
C1 O1A C1B . . 115.89(15) ?
O1A C1B C1C . . 107.24(18) ?
O1A C1B H1B1 . . 109.9(12) ?
C1C C1B H1B1 . . 111.0(13) ?
O1A C1B H1B2 . . 109.0(12) ?
C1C C1B H1B2 . . 111.9(12) ?
H1B1 C1B H1B2 . . 107.7(17) ?
C1B C1C H1C1 . . 109.5 ?
C1B C1C H1C2 . . 109.5 ?
H1C1 C1C H1C2 . . 109.5 ?
C1B C1C H1C3 . . 109.5 ?
H1C1 C1C H1C3 . . 109.5 ?
H1C2 C1C H1C3 . . 109.5 ?
C3 O2 C1 . . 117.55(15) n
O2 C3 C7A . . 122.45(18) ?
O2 C3 C4 . . 115.67(17) ?
C7A C3 C4 . . 121.88(19) ?
C5 C4 C3 . . 121.08(19) ?
C5 C4 H4A . . 119.3(12) ?
C3 C4 H4A . . 119.6(12) ?
C4 C5 C6 . . 117.72(19) ?
C4 C5 C5A . . 121.32(18) ?
C6 C5 C5A . . 120.93(18) ?
C5 C5A H51 . . 109.5 ?
C5 C5A H52 . . 109.5 ?
H51 C5A H52 . . 109.5 ?
C5 C5A H53 . . 109.5 ?
H51 C5A H53 . . 109.5 ?
H52 C5A H53 . . 109.5 ?
C5 C6 C7 . . 120.8(2) ?
C5 C6 H6A . . 120.4(11) ?
C7 C6 H6A . . 118.8(11) ?
C7A C7 C6 . . 121.9(2) ?
C7A C7 H7A . . 119.4(12) ?
C6 C7 H7A . . 118.7(12) ?
C3 C7A C7 . . 116.55(19) ?
C3 C7A C8 . . 120.42(18) ?
C7 C7A C8 . . 122.99(17) ?
C9A C8 C15 . . 105.53(16) ?
C9A C8 C8A . . 113.52(16) ?
C15 C8 C8A . . 109.48(16) ?
C9A C8 C7A . . 108.30(15) ?
C15 C8 C7A . . 107.35(16) ?
C8A C8 C7A . . 112.28(16) ?
C8 C8A H81 . . 109.5 ?
C8 C8A H82 . . 109.5 ?
H81 C8A H82 . . 109.5 ?
C8 C8A H83 . . 109.5 ?
H81 C8A H83 . . 109.5 ?
H82 C8A H83 . . 109.5 ?
C9 C9A C13 . . 117.17(19) ?
C9 C9A C8 . . 123.89(19) ?
C13 C9A C8 . . 118.92(17) ?
C9A C9 C10 . . 120.9(2) ?
C9A C9 H9A . . 119.4(11) ?
C10 C9 H9A . . 119.7(11) ?
C9 C10 C11 . . 121.6(2) ?
C9 C10 H10A . . 120.4(12) ?
C11 C10 H10A . . 118.0(12) ?
C12 C11 C10 . . 117.93(19) ?
C12 C11 C11A . . 120.07(19) ?
C10 C11 C11A . . 121.97(19) ?
C11 C11A H111 . . 109.5 ?
C11 C11A H112 . . 109.5 ?
H111 C11A H112 . . 109.5 ?
C11 C11A H113 . . 109.5 ?
H111 C11A H113 . . 109.5 ?
H112 C11A H113 . . 109.5 ?
C13 C12 C11 . . 119.6(2) ?
C13 C12 H12A . . 120.0(14) ?
C11 C12 H12A . . 120.4(14) ?
O14 C13 C12 . . 114.50(18) ?
O14 C13 C9A . . 122.64(18) ?
C12 C13 C9A . . 122.85(19) ?
C13 O14 C1 . . 119.16(15) n
C1 C15 C8 . . 108.64(17) n
C1 C15 H15A . . 110.6(12) ?
C8 C15 H15A . . 107.0(12) ?
C1 C15 H15B . . 110.1(12) ?
C8 C15 H15B . . 110.6(12) ?
H15A C15 H15B . . 109.9(17) ?
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
C1 O1A . 1.394(2) n
C1 O14 . 1.441(2) n
C1 O2 . 1.447(2) ?
C1 C15 . 1.516(3) n
O1A C1B . 1.471(3) ?
C1B C1C . 1.506(3) ?
C1B H1B1 . 1.01(2) ?
C1B H1B2 . 1.03(2) ?
C1C H1C1 . 0.9600 ?
C1C H1C2 . 0.9600 ?
C1C H1C3 . 0.9600 ?
O2 C3 . 1.402(2) n
C3 C7A . 1.408(3) ?
C3 C4 . 1.417(3) ?
C4 C5 . 1.401(3) ?
C4 H4A . 1.00(2) ?
C5 C6 . 1.412(3) ?
C5 C5A . 1.537(3) ?
C5A H51 . 0.9600 ?
C5A H52 . 0.9600 ?
C5A H53 . 0.9600 ?
C6 C7 . 1.416(3) ?
C6 H6A . 1.01(2) ?
C7 C7A . 1.410(3) ?
C7 H7A . 0.97(2) ?
C7A C8 . 1.561(3) ?
C8 C9A . 1.545(3) ?
C8 C15 . 1.545(3) n
C8 C8A . 1.549(3) ?
C8A H81 . 0.9600 ?
C8A H82 . 0.9600 ?
C8A H83 . 0.9600 ?
C9A C9 . 1.396(3) ?
C9A C13 . 1.406(3) ?
C9 C10 . 1.404(3) ?
C9 H9A . 1.02(2) ?
C10 C11 . 1.412(3) ?
C10 H10A . 1.01(2) ?
C11 C12 . 1.404(3) ?
C11 C11A . 1.521(3) ?
C11A H111 . 0.9600 ?
C11A H112 . 0.9600 ?
C11A H113 . 0.9600 ?
C12 C13 . 1.404(3) ?
C12 H12A . 0.97(2) ?
C13 O14 . 1.394(2) n
C15 H15A . 1.03(2) ?
C15 H15B . 1.01(2) ?
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
O14 C1 O1A C1B . . . . 52.0(2) ?
O2 C1 O1A C1B . . . . -62.9(2) ?
C15 C1 O1A C1B . . . . 174.86(18) ?
C1 O1A C1B C1C . . . . 177.22(17) ?
O1A C1 O2 C3 . . . . -159.04(15) ?
O14 C1 O2 C3 . . . . 87.06(19) ?
C15 C1 O2 C3 . . . . -37.8(2) ?
C1 O2 C3 C7A . . . . 5.5(3) ?
C1 O2 C3 C4 . . . . -174.66(17) ?
O2 C3 C4 C5 . . . . 178.45(17) ?
C7A C3 C4 C5 . . . . -1.7(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C3 C4 C5 C5A . . . . 177.54(18) ?
C4 C5 C6 C7 . . . . 2.0(3) ?
C5A C5 C6 C7 . . . . -176.14(19) ?
C5 C6 C7 C7A . . . . -1.2(3) ?
O2 C3 C7A C7 . . . . -177.66(17) ?
C4 C3 C7A C7 . . . . 2.5(3) ?
O2 C3 C7A C8 . . . . 0.3(3) ?
C4 C3 C7A C8 . . . . -179.47(18) ?
C6 C7 C7A C3 . . . . -1.1(3) ?
C6 C7 C7A C8 . . . . -179.04(18) ?
C3 C7A C8 C9A . . . . -88.6(2) ?
C7 C7A C8 C9A . . . . 89.3(2) ?
C3 C7A C8 C15 . . . . 24.9(2) ?
C7 C7A C8 C15 . . . . -157.21(19) ?
C3 C7A C8 C8A . . . . 145.29(18) ?
C7 C7A C8 C8A . . . . -36.8(3) ?
C15 C8 C9A C9 . . . . 147.7(2) ?
C8A C8 C9A C9 . . . . 27.8(3) ?
C7A C8 C9A C9 . . . . -97.6(2) ?
C15 C8 C9A C13 . . . . -33.8(2) ?
C8A C8 C9A C13 . . . . -153.74(18) ?
C7A C8 C9A C13 . . . . 80.8(2) ?
C13 C9A C9 C10 . . . . -0.3(3) ?
C8 C9A C9 C10 . . . . 178.18(18) ?
C9A C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C9 C10 C11 C11A . . . . -177.78(19) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
C11A C11 C12 C13 . . . . 177.37(19) ?
C11 C12 C13 O14 . . . . -178.21(17) ?
C11 C12 C13 C9A . . . . 0.7(3) ?
C9 C9A C13 O14 . . . . 178.71(18) ?
C8 C9A C13 O14 . . . . 0.1(3) ?
C9 C9A C13 C12 . . . . -0.1(3) ?
C8 C9A C13 C12 . . . . -178.73(18) ?
C12 C13 O14 C1 . . . . -174.43(17) ?
C9A C13 O14 C1 . . . . 6.6(3) ?
O1A C1 O14 C13 . . . . 144.54(16) ?
O2 C1 O14 C13 . . . . -101.23(18) ?
C15 C1 O14 C13 . . . . 23.2(2) ?
O1A C1 C15 C8 . . . . -177.26(16) ?
O14 C1 C15 C8 . . . . -58.4(2) ?
O2 C1 C15 C8 . . . . 63.7(2) ?
C9A C8 C15 C1 . . . . 61.0(2) ?
C8A C8 C15 C1 . . . . -176.52(17) ?
C7A C8 C15 C1 . . . . -54.4(2) ?
