#------------------------------------------------------------------------------
#$Date: 2015-07-08 07:03:08 +0300 (Wed, 08 Jul 2015) $
#$Revision: 140997 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/09/2240913.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_2240913
loop_
_publ_author_name
'Rousselin, Yoann'
'Laureano, Hugo'
'Clavel, Alexandre'
_publ_section_title
;
 Crystal structure of
 (R)-6-fluoro-2-[(S)-oxiran-2-yl]chroman
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o552
_journal_page_last               o553
_journal_paper_doi               10.1107/S205698901501261X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C11 H11 F O2'
_chemical_formula_moiety         'C11 H11 F O2'
_chemical_formula_sum            'C11 H11 F O2'
_chemical_formula_weight         194.20
_chemical_name_systematic
;
(R)-6-Fluoro-2-[(S)-oxiran-2-yl]chroman
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3742(3)
_cell_length_b                   4.76845(12)
_cell_length_c                   11.0212(3)
_cell_measurement_reflns_used    7897
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.2629
_cell_measurement_theta_min      4.3956
_cell_volume                     449.35(3)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 5.2474
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14207
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.463
_diffrn_reflns_theta_min         4.398
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       needle
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.160
_refine_ls_abs_structure_details
;
crystal refined as an inversion twin (Flack, 2003)
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1847
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0318
_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)+(0.0529P)²+0.0952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                1820
_reflns_number_total             1847
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gk2636sup1.cif
_cod_data_source_block           I
_cod_database_code               2240913
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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_occupancy
C C1 0.7376(2) 0.5622(5) 0.50701(19) 0.0255(4) Uani d 1
C C6 0.8296(2) 0.4711(5) 0.4448(2) 0.0254(4) Uani d 1
H H6 0.9095 0.3366 0.4870 0.030 Uiso calc 1
C C5 0.8061(2) 0.5754(4) 0.32005(19) 0.0226(4) Uani d 1
C C4 0.6872(2) 0.7732(4) 0.26151(18) 0.0214(4) Uani d 1
C C3 0.5962(2) 0.8655(5) 0.3267(2) 0.0255(4) Uani d 1
H H3 0.5165 1.0009 0.2857 0.031 Uiso calc 1
C C2 0.6216(2) 0.7604(5) 0.4512(2) 0.0261(4) Uani d 1
H H2 0.5608 0.8231 0.4968 0.031 Uiso calc 1
C C7 0.9061(2) 0.4801(4) 0.24929(19) 0.0253(4) Uani d 1
H H7A 0.8759 0.2868 0.2157 0.030 Uiso calc 1
H H7B 1.0172 0.4770 0.3132 0.030 Uiso calc 1
C C8 0.8876(2) 0.6721(5) 0.13380(19) 0.0240(4) Uani d 1
H H8A 0.9306 0.5803 0.0755 0.029 Uiso calc 1
H H8B 0.9458 0.8488 0.1678 0.029 Uiso calc 1
C C9 0.7148(2) 0.7350(5) 0.05528(19) 0.0235(4) Uani d 1
H H9 0.6568 0.5539 0.0267 0.028 Uiso calc 1
C C10 0.6765(2) 0.9185(5) -0.0645(2) 0.0271(4) Uani d 1
H H10 0.5651 0.9814 -0.1082 0.033 Uiso calc 1
C C11 0.7573(2) 0.8967(5) -0.1530(2) 0.0286(5) Uani d 1
H H11A 0.8377 0.7487 -0.1340 0.034 Uiso calc 1
H H11B 0.6968 0.9384 -0.2485 0.034 Uiso calc 1
O O1 0.65326(15) 0.8871(3) 0.13795(13) 0.0246(3) Uani d 1
O O2 0.79031(19) 1.1254(4) -0.06003(15) 0.0329(4) Uani d 1
F F1 0.76157(14) 0.4549(3) 0.62882(12) 0.0333(3) Uani 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C6 C1 C2 122.35(18)
F1 C1 C6 119.21(18)
F1 C1 C2 118.43(17)
C1 C6 H6 119.9
C1 C6 C5 120.12(19)
C5 C6 H6 119.9
C6 C5 C4 118.06(17)
C6 C5 C7 121.35(18)
C4 C5 C7 120.59(17)
C3 C4 C5 121.04(18)
O1 C4 C5 122.66(16)
O1 C4 C3 116.30(17)
C4 C3 H3 119.9
C2 C3 C4 120.19(19)
C2 C3 H3 119.9
C1 C2 C3 118.22(17)
C1 C2 H2 120.9
C3 C2 H2 120.9
C5 C7 H7A 109.3
C5 C7 H7B 109.3
C5 C7 C8 111.62(16)
H7A C7 H7B 108.0
C8 C7 H7A 109.3
C8 C7 H7B 109.3
C7 C8 H8A 109.9
C7 C8 H8B 109.9
C7 C8 C9 108.92(16)
H8A C8 H8B 108.3
C9 C8 H8A 109.9
C9 C8 H8B 109.9
C8 C9 H9 108.9
C10 C9 C8 115.48(16)
C10 C9 H9 108.9
O1 C9 C8 110.18(15)
O1 C9 H9 108.9
O1 C9 C10 104.31(16)
C9 C10 H10 115.1
C11 C10 C9 122.88(19)
C11 C10 H10 115.1
O2 C10 C9 117.62(16)
O2 C10 H10 115.1
O2 C10 C11 59.51(13)
C10 C11 H11A 117.8
C10 C11 H11B 117.8
H11A C11 H11B 115.0
O2 C11 C10 59.42(13)
O2 C11 H11A 117.8
O2 C11 H11B 117.8
C4 O1 C9 115.60(15)
C10 O2 C11 61.08(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.374(3)
C1 C2 1.381(3)
C1 F1 1.366(2)
C6 H6 0.9500
C6 C5 1.392(3)
C5 C4 1.399(3)
C5 C7 1.514(2)
C4 C3 1.393(3)
C4 O1 1.377(2)
C3 H3 0.9500
C3 C2 1.387(3)
C2 H2 0.9500
C7 H7A 0.9900
C7 H7B 0.9900
C7 C8 1.519(3)
C8 H8A 0.9900
C8 H8B 0.9900
C8 C9 1.521(2)
C9 H9 1.0000
C9 C10 1.500(3)
C9 O1 1.456(2)
C10 H10 1.0000
C10 C11 1.463(3)
C10 O2 1.439(3)
C11 H11A 0.9900
C11 H11B 0.9900
C11 O2 1.440(3)
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
C1 C6 C5 C4 0.0(3)
C1 C6 C5 C7 179.71(17)
C6 C1 C2 C3 1.3(3)
C6 C5 C4 C3 0.7(3)
C6 C5 C4 O1 -179.29(18)
C6 C5 C7 C8 -165.51(18)
C5 C4 C3 C2 -0.4(3)
C5 C4 O1 C9 17.2(2)
C5 C7 C8 C9 -44.7(2)
C4 C5 C7 C8 14.2(2)
C4 C3 C2 C1 -0.5(3)
C3 C4 O1 C9 -162.78(17)
C2 C1 C6 C5 -1.0(3)
C7 C5 C4 C3 -178.99(18)
C7 C5 C4 O1 1.0(3)
C7 C8 C9 C10 -178.77(17)
C7 C8 C9 O1 63.4(2)
C8 C9 C10 C11 38.9(3)
C8 C9 C10 O2 -31.0(3)
C8 C9 O1 C4 -49.5(2)
C9 C10 C11 O2 -105.1(2)
C9 C10 O2 C11 113.8(2)
C10 C9 O1 C4 -174.00(14)
O1 C4 C3 C2 179.56(17)
O1 C9 C10 C11 159.93(19)
O1 C9 C10 O2 90.0(2)
F1 C1 C6 C5 179.30(18)
F1 C1 C2 C3 -179.04(19)

_cod_database_fobs_code 2240913
