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#$Date: 2022-09-21 11:02:27 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105815.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105815
loop_
_publ_author_name
'Li-Hua, Wang'
'Dan-Dan, Lin'
_publ_section_title
;
 The crystal structure of
 4,10-diethoxy-6H,12H-6,12-epoxydibenzo[b,f][1,5]dioxocine, C18H18O5
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              673
_journal_page_last               674
_journal_paper_doi               10.1515/ncrs-2019-0021
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 102.81(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.762(2)
_cell_length_b                   11.832(2)
_cell_length_c                   13.376(3)
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5213
_cell_measurement_theta_min      2.5432
_cell_volume                     1506.5(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  bruker-CCd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14441
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.124
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0645P)²+0.0933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2032
_reflns_number_total             3441
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0021_suppl.cif
_cod_data_source_block           qq
_cod_database_code               8105815
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C17(H17A,H17B)
2.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47024(12) 0.66496(12) 0.75818(9) 0.0498(4) Uani 1 1 d . . . . .
O2 O 0.22425(12) 0.77132(11) 0.71009(8) 0.0450(3) Uani 1 1 d . . . . .
O4 O -0.00790(13) 0.79578(10) 0.45279(9) 0.0500(4) Uani 1 1 d . . . . .
O5 O -0.16820(14) 0.63813(10) 0.35135(9) 0.0499(4) Uani 1 1 d . . . . .
C1 C 0.6419(2) 0.5931(2) 0.89907(17) 0.0703(6) Uani 1 1 d . . . . .
H1A H 0.731364 0.556087 0.918259 0.105 Uiso 1 1 calc R . . . .
H1B H 0.646783 0.665328 0.932411 0.105 Uiso 1 1 calc R . . . .
H1C H 0.571501 0.547490 0.919517 0.105 Uiso 1 1 calc R . . . .
C2 C 0.6045(2) 0.60943(19) 0.78539(16) 0.0571(5) Uani 1 1 d . . . . .
H2A H 0.675457 0.655057 0.764068 0.068 Uiso 1 1 calc R . . . .
H2B H 0.599923 0.536825 0.751131 0.068 Uiso 1 1 calc R . . . .
C3 C 0.42183(18) 0.69282(15) 0.65734(13) 0.0430(4) Uani 1 1 d . . . . .
C4 C 0.4875(2) 0.66558(18) 0.57871(15) 0.0537(5) Uani 1 1 d . . . . .
H4 H 0.571212 0.625068 0.592952 0.064 Uiso 1 1 calc R . . . .
C5 C 0.4286(2) 0.69866(19) 0.47823(16) 0.0602(6) Uani 1 1 d . . . . .
H5 H 0.471925 0.677826 0.425735 0.072 Uiso 1 1 calc R . . . .
C6 C 0.3079(2) 0.76129(18) 0.45594(14) 0.0541(5) Uani 1 1 d . . . . .
H6 H 0.271733 0.785724 0.389227 0.065 Uiso 1 1 calc R . . . .
C7 C 0.23956(19) 0.78823(15) 0.53361(13) 0.0437(4) Uani 1 1 d . . . . .
C8 C 0.29397(18) 0.75171(15) 0.63288(12) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.1071(2) 0.85819(15) 0.51168(14) 0.0495(5) Uani 1 1 d . . . . .
H9 H 0.123252 0.924383 0.471753 0.059 Uiso 1 1 d R . . . .
C10 C 0.08058(18) 0.80300(15) 0.67050(14) 0.0457(4) Uani 1 1 d . . . . .
H10 H 0.040338 0.826132 0.728251 0.055 Uiso 1 1 d R . . . .
C11 C -0.00760(18) 0.70818(15) 0.61564(13) 0.0412(4) Uani 1 1 d . . . . .
C12 C -0.05493(18) 0.62095(16) 0.66958(14) 0.0470(5) Uani 1 1 d . . . . .
H12 H -0.028647 0.618714 0.740763 0.056 Uiso 1 1 calc R . . . .
C13 C -0.14045(19) 0.53847(16) 0.61704(15) 0.0498(5) Uani 1 1 d . . . . .
H13 H -0.171393 0.480219 0.653185 0.060 Uiso 1 1 calc R . . . .
C14 C -0.18165(19) 0.54055(15) 0.51058(14) 0.0469(5) Uani 1 1 d . . . . .
H14 H -0.239469 0.483827 0.476255 0.056 Uiso 1 1 calc R . . . .
C15 C -0.13678(18) 0.62685(14) 0.45560(13) 0.0416(4) Uani 1 1 d . . . . .
C16 C -0.04902(17) 0.71074(14) 0.50948(13) 0.0401(4) Uani 1 1 d . . . . .
C17 C -0.2611(2) 0.55634(17) 0.29346(15) 0.0517(5) Uani 1 1 d . . . . .
H17A H -0.352965 0.561521 0.309600 0.062 Uiso 1 1 calc R . . . .
H17B H -0.224724 0.480748 0.310232 0.062 Uiso 1 1 calc R . . . .
C18 C -0.2723(2) 0.5797(2) 0.18205(15) 0.0660(6) Uani 1 1 d . . . . .
H18A H -0.334334 0.525563 0.141815 0.099 Uiso 1 1 calc R . . . .
H18B H -0.308798 0.654455 0.166098 0.099 Uiso 1 1 calc R . . . .
H18C H -0.181033 0.573982 0.166728 0.099 Uiso 1 1 calc R . . . .
O3 O 0.07534(14) 0.89692(11) 0.60408(10) 0.0529(4) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O1 C2 117.12(15) . .
C8 O2 C10 111.88(13) . .
C16 O4 C9 111.43(13) . .
C15 O5 C17 117.28(14) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
O1 C2 C1 108.64(17) . .
O1 C2 H2A 110.0 . .
O1 C2 H2B 110.0 . .
C1 C2 H2A 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.3 . .
O1 C3 C4 125.18(17) . .
O1 C3 C8 116.41(15) . .
C4 C3 C8 118.41(17) . .
C3 C4 H4 119.9 . .
C3 C4 C5 120.3(2) . .
C5 C4 H4 119.9 . .
C4 C5 H5 119.6 . .
C6 C5 C4 120.88(19) . .
C6 C5 H5 119.6 . .
C5 C6 H6 120.2 . .
C5 C6 C7 119.62(18) . .
C7 C6 H6 120.2 . .
C6 C7 C9 120.88(17) . .
C8 C7 C6 119.95(18) . .
C8 C7 C9 119.17(17) . .
O2 C8 C3 118.09(15) . .
O2 C8 C7 121.21(16) . .
C7 C8 C3 120.69(17) . .
O4 C9 C7 111.04(15) . .
O4 C9 H9 108.3 . .
C7 C9 H9 108.1 . .
O3 C9 O4 110.60(16) . .
O3 C9 C7 110.62(14) . .
O3 C9 H9 108.1 . .
O2 C10 H10 108.2 . .
O2 C10 C11 113.10(14) . .
C11 C10 H10 107.9 . .
O3 C10 O2 109.44(15) . .
O3 C10 H10 108.1 . .
O3 C10 C11 110.02(14) . .
C12 C11 C10 121.29(16) . .
C16 C11 C10 119.26(16) . .
C16 C11 C12 119.36(17) . .
C11 C12 H12 120.2 . .
C13 C12 C11 119.66(17) . .
C13 C12 H12 120.2 . .
C12 C13 H13 119.4 . .
C12 C13 C14 121.10(17) . .
C14 C13 H13 119.4 . .
C13 C14 H14 119.9 . .
C15 C14 C13 120.18(17) . .
C15 C14 H14 119.9 . .
O5 C15 C14 126.02(16) . .
O5 C15 C16 115.40(15) . .
C14 C15 C16 118.57(16) . .
O4 C16 C11 121.79(15) . .
O4 C16 C15 117.09(15) . .
C11 C16 C15 121.12(16) . .
O5 C17 H17A 110.1 . .
O5 C17 H17B 110.1 . .
O5 C17 C18 108.19(16) . .
H17A C17 H17B 108.4 . .
C18 C17 H17A 110.1 . .
C18 C17 H17B 110.1 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C9 O3 C10 108.01(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.439(2) .
O1 C3 1.367(2) .
O2 C8 1.377(2) .
O2 C10 1.435(2) .
O4 C9 1.426(2) .
O4 C16 1.372(2) .
O5 C15 1.366(2) .
O5 C17 1.431(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 C2 1.496(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.386(3) .
C3 C8 1.403(3) .
C4 H4 0.9300 .
C4 C5 1.396(3) .
C5 H5 0.9300 .
C5 C6 1.367(3) .
C6 H6 0.9300 .
C6 C7 1.390(3) .
C7 C8 1.385(2) .
C7 C9 1.508(3) .
C9 H9 0.9802 .
C9 O3 1.416(2) .
C10 H10 0.9800 .
C10 C11 1.503(2) .
C10 O3 1.417(2) .
C11 C12 1.395(3) .
C11 C16 1.388(2) .
C12 H12 0.9300 .
C12 C13 1.372(3) .
C13 H13 0.9300 .
C13 C14 1.391(2) .
C14 H14 0.9300 .
C14 C15 1.385(3) .
C15 C16 1.402(2) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.495(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C3 C4 C5 -179.88(17) . . . .
O1 C3 C8 O2 -3.4(2) . . . .
O1 C3 C8 C7 177.01(15) . . . .
O2 C10 C11 C12 76.8(2) . . . .
O2 C10 C11 C16 -106.71(18) . . . .
O2 C10 O3 C9 73.77(17) . . . .
O4 C9 O3 C10 73.42(17) . . . .
O5 C15 C16 O4 1.8(2) . . . .
O5 C15 C16 C11 -179.09(15) . . . .
C2 O1 C3 C4 4.2(3) . . . .
C2 O1 C3 C8 -177.07(16) . . . .
C3 O1 C2 C1 176.47(17) . . . .
C3 C4 C5 C6 2.1(3) . . . .
C4 C3 C8 O2 175.38(16) . . . .
C4 C3 C8 C7 -4.2(3) . . . .
C4 C5 C6 C7 -2.8(3) . . . .
C5 C6 C7 C8 0.1(3) . . . .
C5 C6 C7 C9 179.36(17) . . . .
C6 C7 C8 O2 -176.10(16) . . . .
C6 C7 C8 C3 3.5(3) . . . .
C6 C7 C9 O4 70.6(2) . . . .
C6 C7 C9 O3 -166.22(16) . . . .
C7 C9 O3 C10 -50.04(18) . . . .
C8 O2 C10 C11 68.46(19) . . . .
C8 O2 C10 O3 -54.58(18) . . . .
C8 C3 C4 C5 1.5(3) . . . .
C8 C7 C9 O4 -110.13(18) . . . .
C8 C7 C9 O3 13.1(2) . . . .
C9 O4 C16 C11 15.8(2) . . . .
C9 O4 C16 C15 -165.08(16) . . . .
C9 C7 C8 O2 4.6(2) . . . .
C9 C7 C8 C3 -175.81(16) . . . .
C10 O2 C8 C3 -163.86(15) . . . .
C10 O2 C8 C7 15.7(2) . . . .
C10 C11 C12 C13 177.09(16) . . . .
C10 C11 C16 O4 2.1(3) . . . .
C10 C11 C16 C15 -176.94(16) . . . .
C11 C10 O3 C9 -51.09(18) . . . .
C11 C12 C13 C14 -0.4(3) . . . .
C12 C11 C16 O4 178.67(16) . . . .
C12 C11 C16 C15 -0.4(3) . . . .
C12 C13 C14 C15 -0.2(3) . . . .
C13 C14 C15 O5 179.25(17) . . . .
C13 C14 C15 C16 0.4(3) . . . .
C14 C15 C16 O4 -179.21(16) . . . .
C14 C15 C16 C11 -0.1(3) . . . .
C15 O5 C17 C18 -175.93(17) . . . .
C16 O4 C9 C7 70.0(2) . . . .
C16 O4 C9 O3 -53.27(19) . . . .
C16 C11 C12 C13 0.6(3) . . . .
C17 O5 C15 C14 3.0(3) . . . .
C17 O5 C15 C16 -178.08(15) . . . .
O3 C10 C11 C12 -160.46(17) . . . .
O3 C10 C11 C16 16.0(2) . . . .
