#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/57/2205734.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_2205734
loop_
_publ_author_name
'Jian-Hua Zhong'
'Shan-Zhong Jian'
'Xue-Ying He'
'Yan-Guang Wang'
_publ_section_title
(5α,8α,9β,11S)-5,7,8,9-Tetrahydro-11-(fluoromethyl)-9-(3,4,5-trimethoxyphenyl)-5,8-methano-1,3-dioxolo[4,5-h][2]benzoxepin
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1280
_journal_page_last               o1282
_journal_paper_doi               10.1107/S1600536805010366
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C22 H23 F O6'
_chemical_formula_sum            'C22 H23 F O6'
_chemical_formula_weight         402.4
_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                   7.22530(10)
_cell_length_b                   8.12170(10)
_cell_length_c                   32.7768(4)
_cell_measurement_reflns_used    22120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.2
_cell_volume                     1923.40(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14274
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.39
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_gt           0.05
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0946P)²+0.3221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                2296
_reflns_number_total             2519
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6164.cif
_cod_data_source_block           3
_cod_database_code               2205734
_cod_database_fobs_code          2205734
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
F1 0.3768(4) 0.1661(4) 0.43426(8) 0.0943(9) Uani d . 1 F
O1 0.1314(3) 0.5638(3) 0.34866(7) 0.0489(5) Uani d . 1 O
O2 0.5840(4) 0.3373(4) 0.21736(7) 0.0692(8) Uani d . 1 O
O3 0.8477(3) 0.4349(4) 0.24895(6) 0.0632(7) Uani d . 1 O
O4 0.8202(4) 1.0503(3) 0.36740(6) 0.0521(6) Uani d . 1 O
O5 0.9504(3) 1.0411(3) 0.44375(7) 0.0481(5) Uani d . 1 O
O6 0.8829(3) 0.7823(3) 0.49289(5) 0.0446(5) Uani d . 1 O
C1 0.5417(3) 0.4926(3) 0.38474(7) 0.0298(5) Uani d . 1 C
H1 0.602 0.3967 0.3971 0.036 Uiso calc R 1 H
C2 0.3417(4) 0.4952(4) 0.40196(8) 0.0393(6) Uani d . 1 C
H2 0.3426 0.5016 0.4318 0.047 Uiso calc R 1 H
C3 0.2236(4) 0.6323(4) 0.38366(10) 0.0478(7) Uani d . 1 C
H3A 0.1337 0.6709 0.4034 0.057 Uiso calc R 1 H
H3B 0.3009 0.7243 0.3756 0.057 Uiso calc R 1 H
C4 0.2338(4) 0.3426(4) 0.38727(9) 0.0440(7) Uani d . 1 C
H4 0.1139 0.3406 0.4012 0.053 Uiso calc R 1 H
C5 0.3253(5) 0.1791(4) 0.39322(10) 0.0549(8) Uani d . 1 C
H5A 0.2404 0.0911 0.3861 0.066 Uiso calc R 1 H
H5B 0.4336 0.1705 0.3759 0.066 Uiso calc R 1 H
C6 0.2027(4) 0.3987(4) 0.34330(9) 0.0418(6) Uani d . 1 C
H6 0.1115 0.3285 0.3296 0.05 Uiso calc R 1 H
C7 0.3806(4) 0.4045(3) 0.31951(8) 0.0364(6) Uani d . 1 C
C8 0.3818(4) 0.3607(4) 0.27804(9) 0.0434(7) Uani d . 1 C
H8 0.2752 0.3239 0.265 0.052 Uiso calc R 1 H
C9 0.5451(4) 0.3743(4) 0.25763(8) 0.0453(7) Uani d . 1 C
C10 0.7756(6) 0.3642(8) 0.21299(11) 0.0860(16) Uani d . 1 C
H10A 0.798 0.4371 0.1901 0.103 Uiso calc R 1 H
H10B 0.8375 0.2605 0.2076 0.103 Uiso calc R 1 H
C11 0.7041(4) 0.4324(4) 0.27640(8) 0.0392(6) Uani d . 1 C
C12 0.7075(3) 0.4749(3) 0.31684(8) 0.0342(5) Uani d . 1 C
H12 0.8156 0.5117 0.3292 0.041 Uiso calc R 1 H
C13 0.5419(3) 0.4609(3) 0.33877(7) 0.0303(5) Uani d . 1 C
C14 0.6516(3) 0.6412(3) 0.39879(7) 0.0296(5) Uani d . 1 C
C15 0.6782(4) 0.7793(3) 0.37453(7) 0.0340(5) Uani d . 1 C
H15 0.6293 0.7832 0.3483 0.041 Uiso calc R 1 H
C16 0.7790(4) 0.9123(3) 0.38980(8) 0.0355(6) Uani d . 1 C
C17 0.8456(4) 0.9117(3) 0.42968(8) 0.0345(5) Uani d . 1 C
C18 0.8149(3) 0.7732(3) 0.45409(7) 0.0325(5) Uani d . 1 C
C19 0.7212(3) 0.6381(3) 0.43852(7) 0.0320(5) Uani d . 1 C
H19 0.7046 0.545 0.4546 0.038 Uiso calc R 1 H
C20 0.7856(5) 1.0437(4) 0.32491(9) 0.0544(8) Uani d . 1 C
H20A 0.6553 1.0554 0.32 0.082 Uiso calc R 1 H
H20B 0.8271 0.9398 0.3143 0.082 Uiso calc R 1 H
H20C 0.851 1.1313 0.3115 0.082 Uiso calc R 1 H
C21 0.8560(7) 1.1537(5) 0.46829(13) 0.0727(11) Uani d . 1 C
H21A 0.7951 1.0962 0.4901 0.109 Uiso calc R 1 H
H21B 0.7656 1.211 0.4522 0.109 Uiso calc R 1 H
H21C 0.9423 1.2314 0.4795 0.109 Uiso calc R 1 H
C22 0.8616(4) 0.6388(4) 0.51769(8) 0.0458(7) Uani d . 1 C
H22A 0.9263 0.5483 0.5054 0.069 Uiso calc R 1 H
H22B 0.7326 0.6121 0.52 0.069 Uiso calc R 1 H
H22C 0.9116 0.6596 0.5443 0.069 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 0.0033 0.0016 '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 0.0106 0.006 '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
_geom_angle_publ_flag
C3 O1 C6 106.9(2) y
C9 O2 C10 105.3(3) y
C11 O3 C10 105.2(3) ?
C16 O4 C20 117.2(2) y
C17 O5 C21 115.1(3) ?
C18 O6 C22 116.5(2) ?
C14 C1 C13 115.7(2) ?
C14 C1 C2 111.5(2) ?
C13 C1 C2 111.20(18) ?
C14 C1 H1 105.9 ?
C13 C1 H1 105.9 ?
C2 C1 H1 105.9 ?
C3 C2 C4 100.4(2) ?
C3 C2 C1 112.8(2) ?
C4 C2 C1 110.3(2) ?
C3 C2 H2 111 ?
C4 C2 H2 111 ?
C1 C2 H2 111 ?
O1 C3 C2 106.9(2) y
O1 C3 H3A 110.3 ?
C2 C3 H3A 110.3 ?
O1 C3 H3B 110.3 ?
C2 C3 H3B 110.3 ?
H3A C3 H3B 108.6 ?
C5 C4 C6 116.9(3) ?
C5 C4 C2 116.7(3) ?
C6 C4 C2 97.4(2) ?
C5 C4 H4 108.4 ?
C6 C4 H4 108.4 ?
C2 C4 H4 108.4 ?
F1 C5 C4 108.0(3) y
F1 C5 H5A 110.1 ?
C4 C5 H5A 110.1 ?
F1 C5 H5B 110.1 ?
C4 C5 H5B 110.1 ?
H5A C5 H5B 108.4 ?
O1 C6 C7 109.8(2) ?
O1 C6 C4 102.4(2) y
C7 C6 C4 111.9(2) ?
O1 C6 H6 110.8 ?
C7 C6 H6 110.8 ?
C4 C6 H6 110.8 ?
C13 C7 C8 120.9(2) ?
C13 C7 C6 119.1(2) ?
C8 C7 C6 120.0(2) ?
C9 C8 C7 117.4(2) ?
C9 C8 H8 121.3 ?
C7 C8 H8 121.3 ?
C8 C9 O2 128.9(3) ?
C8 C9 C11 121.9(2) ?
O2 C9 C11 109.2(3) ?
O2 C10 O3 109.9(3) ?
O2 C10 H10A 109.7 ?
O3 C10 H10A 109.7 ?
O2 C10 H10B 109.7 ?
O3 C10 H10B 109.7 ?
H10A C10 H10B 108.2 ?
C12 C11 O3 128.0(2) ?
C12 C11 C9 122.0(2) ?
O3 C11 C9 109.9(2) ?
C11 C12 C13 117.4(2) ?
C11 C12 H12 121.3 ?
C13 C12 H12 121.3 ?
C12 C13 C7 120.4(2) ?
C12 C13 C1 119.5(2) ?
C7 C13 C1 119.9(2) ?
C15 C14 C19 119.9(2) ?
C15 C14 C1 122.8(2) ?
C19 C14 C1 117.2(2) ?
C14 C15 C16 119.5(2) ?
C14 C15 H15 120.3 ?
C16 C15 H15 120.3 ?
O4 C16 C17 115.5(2) ?
O4 C16 C15 123.6(2) ?
C17 C16 C15 121.0(2) ?
O5 C17 C16 120.2(2) ?
O5 C17 C18 120.7(2) ?
C16 C17 C18 119.0(2) ?
O6 C18 C19 124.2(2) ?
O6 C18 C17 115.6(2) ?
C19 C18 C17 120.2(2) ?
C18 C19 C14 120.3(2) ?
C18 C19 H19 119.8 ?
C14 C19 H19 119.8 ?
O4 C20 H20A 109.5 ?
O4 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
O4 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
O5 C21 H21A 109.5 ?
O5 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O5 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
O6 C22 H22A 109.5 ?
O6 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
O6 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C5 1.400(4) y
O1 C3 1.438(4) y
O1 C6 1.447(4) y
O2 C9 1.383(3) y
O2 C10 1.409(5) y
O3 C11 1.374(3) ?
O3 C10 1.411(4) ?
O4 C16 1.373(3) y
O4 C20 1.416(3) y
O5 C17 1.375(3) ?
O5 C21 1.396(5) ?
O6 C18 1.365(3) ?
O6 C22 1.430(4) ?
C1 C14 1.516(3) ?
C1 C13 1.529(3) ?
C1 C2 1.552(3) ?
C1 H1 0.98 ?
C2 C3 1.526(4) ?
C2 C4 1.541(4) ?
C2 H2 0.98 ?
C3 H3A 0.97 ?
C3 H3B 0.97 ?
C4 C5 1.496(5) ?
C4 C6 1.528(4) ?
C4 H4 0.98 ?
C5 H5A 0.97 ?
C5 H5B 0.97 ?
C6 C7 1.504(4) ?
C6 H6 0.98 ?
C7 C13 1.403(3) ?
C7 C8 1.405(4) ?
C8 C9 1.360(4) ?
C8 H8 0.93 ?
C9 C11 1.386(4) ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
C11 C12 1.370(3) ?
C12 C13 1.401(3) ?
C12 H12 0.93 ?
C14 C15 1.388(4) ?
C14 C19 1.396(3) ?
C15 C16 1.396(4) ?
C15 H15 0.93 ?
C16 C17 1.393(4) ?
C17 C18 1.398(4) ?
C18 C19 1.386(4) ?
C19 H19 0.93 ?
C20 H20A 0.96 ?
C20 H20B 0.96 ?
C20 H20C 0.96 ?
C21 H21A 0.96 ?
C21 H21B 0.96 ?
C21 H21C 0.96 ?
C22 H22A 0.96 ?
C22 H22B 0.96 ?
C22 H22C 0.96 ?
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 H10B O1 4_645 0.9700 2.4500 3.238(6) 138 yes
C12 H12 O1 1_655 0.9300 2.4100 3.315(3) 166 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173403
