#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/11/2231164.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_2231164
loop_
_publ_author_name
'Mehta, Goverdhan'
'Sen, Saikat'
_publ_section_title
;
 (1S*,3S*,8S*,10S*)-10-Fluoro-15-oxatetracyclo[6.6.1.0^1,10^.0^3,8^]pentadeca-5,12-dien-3-ol
;
_journal_coeditor_code           IS2740
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1985
_journal_paper_doi               10.1107/S1600536811026857
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H17 F O2'
_chemical_formula_moiety         'C14 H17 F O2'
_chemical_formula_structural     'C14 H17 F O2'
_chemical_formula_sum            'C14 H17 F O2'
_chemical_formula_weight         236.28
_chemical_name_systematic
;(1S*,3S*,8S*,10S*)-10-Fluoro-15-
oxatetracyclo[6.6.1.0^1,10^.0^3,8^]pentadeca-5,12-dien-3-ol
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 96.285(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1603(6)
_cell_length_b                   10.9148(8)
_cell_length_c                   13.5558(10)
_cell_measurement_reflns_used    4978
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.40
_cell_volume                     1200.13(15)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10752
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0406
_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)+(0.0537P)²+0.3336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2038
_reflns_number_total             2454
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2740.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231164
_cod_database_fobs_code          2231164
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_symmetry_multiplicity
F F1 0.50293(10) -0.03822(8) 0.17755(7) 0.0539(3) Uani d . 1 1
O O1 0.92031(13) -0.15772(9) 0.33199(8) 0.0491(3) Uani d . 1 1
O O2 0.86964(11) 0.13521(8) 0.21690(6) 0.0368(2) Uani d . 1 1
C C1 0.61016(16) 0.05894(12) 0.20951(11) 0.0395(3) Uani d . 1 1
C C10 1.2213(2) 0.0155(2) 0.34728(15) 0.0648(5) Uani d . 1 1
C C11 1.1499(2) 0.08929(18) 0.40684(13) 0.0614(5) Uani d . 1 1
C C12 0.96990(19) 0.11773(14) 0.39499(11) 0.0466(4) Uani d . 1 1
C C13 0.87362(16) 0.05869(11) 0.30592(9) 0.0340(3) Uani d . 1 1
C C14 0.68963(16) 0.03854(13) 0.31557(10) 0.0392(3) Uani d . 1 1
C C2 0.5123(2) 0.17729(15) 0.19553(13) 0.0553(4) Uani d . 1 1
C C3 0.4910(3) 0.21989(19) 0.09124(16) 0.0818(7) Uani d . 1 1
C C4 0.5907(3) 0.18950(17) 0.02523(15) 0.0786(7) Uani d . 1 1
C C5 0.7339(2) 0.10512(18) 0.04581(11) 0.0610(5) Uani d . 1 1
C C6 0.76146(17) 0.05679(12) 0.15111(10) 0.0392(3) Uani d . 1 1
C C7 0.84679(18) -0.06886(13) 0.16311(11) 0.0442(3) Uani d . 1 1
C C8 0.94747(17) -0.05946(12) 0.26624(11) 0.0388(3) Uani d . 1 1
C C9 1.13154(18) -0.04261(15) 0.25771(13) 0.0531(4) Uani d . 1 1
H H1 0.9770 -0.2167 0.3197 0.074 Uiso calc R 1 1
H H2A 0.4045 0.1650 0.2178 0.066 Uiso calc R 1 1
H H2B 0.5683 0.2405 0.2367 0.066 Uiso calc R 1 1
H H3 0.4022 0.2709 0.0713 0.098 Uiso calc R 1 1
H H4 0.5705 0.2227 -0.0381 0.094 Uiso calc R 1 1
H H5A 0.8327 0.1478 0.0313 0.073 Uiso calc R 1 1
H H5B 0.7184 0.0360 0.0008 0.073 Uiso calc R 1 1
H H7A 0.9182 -0.0825 0.1115 0.053 Uiso calc R 1 1
H H7B 0.7666 -0.1346 0.1614 0.053 Uiso calc R 1 1
H H9A 1.1803 -0.1220 0.2473 0.064 Uiso calc R 1 1
H H9B 1.1448 0.0078 0.2002 0.064 Uiso calc R 1 1
H H10 1.3331 -0.0010 0.3620 0.078 Uiso calc R 1 1
H H11 1.2156 0.1257 0.4592 0.074 Uiso calc R 1 1
H H12A 0.9561 0.2058 0.3898 0.056 Uiso calc R 1 1
H H12B 0.9234 0.0913 0.4543 0.056 Uiso calc R 1 1
H H14A 0.6692 -0.0438 0.3382 0.047 Uiso calc R 1 1
H H14B 0.6492 0.0971 0.3610 0.047 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
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
F1 C1 C14 111.36(11)
F1 C1 C2 107.49(11)
F1 C1 C6 109.63(11)
O1 C8 C13 108.46(11)
O1 C8 C7 114.30(11)
O1 C8 C9 111.00(12)
O2 C13 C12 112.20(10)
O2 C13 C14 102.58(10)
O2 C13 C8 99.41(10)
O2 C6 C1 98.18(10)
O2 C6 C5 112.86(12)
O2 C6 C7 102.79(11)
C1 C14 C13 102.54(10)
C1 C14 H14A 111.3
C1 C14 H14B 111.3
C1 C2 H2A 109.0
C1 C2 H2B 109.0
C1 C6 C7 109.80(11)
C2 C1 C14 113.86(12)
C2 C1 C6 112.91(12)
C2 C3 H3 118.2
C3 C2 C1 113.04(15)
C3 C2 H2A 109.0
C3 C2 H2B 109.0
C3 C4 C5 124.00(17)
C3 C4 H4 118.0
C4 C3 C2 123.59(18)
C4 C3 H3 118.2
C4 C5 C6 115.07(16)
C4 C5 H5A 108.5
C4 C5 H5B 108.5
C5 C4 H4 118.0
C5 C6 C1 115.79(13)
C5 C6 C7 115.37(13)
C6 C5 H5A 108.5
C6 C5 H5B 108.5
C6 C7 C8 103.06(11)
C6 C7 H7A 111.2
C6 C7 H7B 111.2
C6 O2 C13 97.25(9)
C8 C7 H7A 111.2
C8 C7 H7B 111.2
C8 C9 H9A 109.0
C8 C9 H9B 109.0
C8 O1 H1 109.5
C9 C10 H10 118.4
C9 C8 C13 110.46(12)
C9 C8 C7 111.63(12)
C10 C11 C12 123.78(15)
C10 C11 H11 118.1
C10 C9 C8 112.88(14)
C10 C9 H9A 109.0
C10 C9 H9B 109.0
C11 C10 C9 123.21(15)
C11 C10 H10 118.4
C11 C12 C13 114.63(14)
C11 C12 H12A 108.6
C11 C12 H12B 108.6
C12 C11 H11 118.1
C12 C13 C14 114.86(12)
C12 C13 C8 116.47(12)
C13 C12 H12A 108.6
C13 C12 H12B 108.6
C13 C14 H14A 111.3
C13 C14 H14B 111.3
C13 C8 C7 100.45(10)
C14 C1 C6 101.55(10)
C14 C13 C8 109.40(10)
H12A C12 H12B 107.6
H14A C14 H14B 109.2
H2A C2 H2B 107.8
H5A C5 H5B 107.5
H7A C7 H7B 109.1
H9A C9 H9B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.4126(15)
O1 C8 1.4272(16)
O1 H1 0.8200
O2 C13 1.4650(15)
O2 C6 1.4611(16)
C1 C14 1.527(2)
C1 C2 1.520(2)
C2 C3 1.480(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 H3 0.9300
C4 C3 1.316(3)
C4 H4 0.9300
C5 C4 1.490(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C1 1.538(2)
C6 C5 1.515(2)
C6 C7 1.5387(19)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C7 1.545(2)
C8 C9 1.530(2)
C9 C10 1.490(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10 0.9300
C11 C10 1.320(3)
C11 H11 0.9300
C12 C11 1.493(2)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C12 1.5109(19)
C13 C14 1.5371(18)
C13 C8 1.5448(18)
C14 H14A 0.9700
C14 H14B 0.9700
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
O1 H1 O2 2_745 0.82 2.14 2.9554(14) 177 yes
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
F1 C1 C14 C13 129.67(11)
F1 C1 C2 C3 -78.24(18)
O1 C8 C7 C6 127.74(11)
O1 C8 C9 C10 -74.33(17)
O2 C13 C12 C11 -88.81(15)
O2 C13 C14 C1 23.37(12)
O2 C13 C8 C7 -43.94(11)
O2 C13 C8 C9 74.02(13)
O2 C13 C8 O1 -164.13(10)
O2 C6 C1 C14 -45.18(11)
O2 C6 C1 C2 77.13(13)
O2 C6 C1 F1 -163.06(10)
O2 C6 C5 C4 -89.78(17)
O2 C6 C7 C8 24.13(13)
C1 C2 C3 C4 -23.8(3)
C1 C6 C5 C4 22.3(2)
C1 C6 C7 C8 -79.56(13)
C2 C1 C14 C13 -108.60(13)
C5 C4 C3 C2 2.2(4)
C5 C6 C1 C14 -165.54(13)
C5 C6 C1 C2 -43.22(17)
C5 C6 C1 F1 76.59(15)
C5 C6 C7 C8 147.40(13)
C6 C1 C14 C13 13.05(12)
C6 C1 C2 C3 42.79(19)
C6 C5 C4 C3 -1.3(3)
C6 O2 C13 C12 -176.26(11)
C6 O2 C13 C14 -52.46(11)
C6 O2 C13 C8 59.99(11)
C7 C6 C1 C14 61.64(13)
C7 C6 C1 C2 -176.04(12)
C7 C6 C1 F1 -56.23(14)
C7 C6 C5 C4 152.45(15)
C7 C8 C9 C10 156.88(14)
C8 C13 C12 C11 24.79(18)
C8 C13 C14 C1 -81.47(12)
C8 C9 C10 C11 -26.7(2)
C9 C8 C7 C6 -105.25(13)
C12 C11 C10 C9 3.5(3)
C12 C13 C14 C1 145.38(11)
C12 C13 C8 C7 -164.63(11)
C12 C13 C8 C9 -46.66(16)
C12 C13 C8 O1 75.19(14)
C13 C12 C11 C10 -2.2(2)
C13 C8 C7 C6 11.85(13)
C13 C8 C9 C10 46.01(18)
C13 O2 C6 C1 60.29(11)
C13 O2 C6 C5 -177.19(12)
C13 O2 C6 C7 -52.26(11)
C14 C1 C2 C3 157.92(15)
C14 C13 C12 C11 154.56(13)
C14 C13 C8 C7 63.06(13)
C14 C13 C8 C9 -178.98(12)
C14 C13 C8 O1 -57.12(14)
