#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/99/2239961.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_2239961
loop_
_publ_author_name
'Shen, Zheng'
'Mao, Qiu-Xia'
'Ge, Ji-Long'
'Tu, Yong-Rui'
'Wang, Yan'
_publ_section_title
;
 Crystal structure of
 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1087
_journal_paper_doi               10.1107/S1600536814019746
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H10 Cl F O2'
_chemical_formula_moiety         'C11 H10 Cl F O2'
_chemical_formula_sum            'C11 H10 Cl F O2'
_chemical_formula_weight         228.64
_chemical_name_systematic
;
2-Chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone
;
_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                 101.637(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.704(3)
_cell_length_b                   9.720(3)
_cell_length_c                   10.804(4)
_cell_measurement_reflns_used    1940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.14
_cell_volume                     998.1(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5810
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.610
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0577
_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)+(0.0870P)²+0.9962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                1701
_reflns_number_total             1940
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5719sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        998.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239961
_cod_database_fobs_code          2239961
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_symmetry_multiplicity
Cl Cl1 0.29999(8) 0.06003(8) 0.46282(7) 0.0520(3) Uani d . 1 1
O O2 0.6337(2) 0.3728(2) 0.50089(17) 0.0446(5) Uani d . 1 1
F F1 1.0157(2) 0.7779(2) 0.4805(2) 0.0693(6) Uani d . 1 1
C C5 0.7331(3) 0.4738(3) 0.5024(2) 0.0370(6) Uani d . 1 1
C C1 0.9201(3) 0.6183(3) 0.6021(3) 0.0465(7) Uani d . 1 1
H H1 0.9827 0.6483 0.6738 0.056 Uiso calc R 1 1
C C6 0.8247(3) 0.5141(3) 0.6117(3) 0.0399(6) Uani d . 1 1
C C4 0.7381(3) 0.5330(3) 0.3864(3) 0.0415(6) Uani d . 1 1
H H4 0.6773 0.5026 0.3137 0.050 Uiso calc R 1 1
C C3 0.8324(3) 0.6361(3) 0.3789(3) 0.0476(7) Uani d . 1 1
H H3 0.8355 0.6776 0.3019 0.057 Uiso calc R 1 1
C C7 0.8214(3) 0.4463(3) 0.7360(3) 0.0504(7) Uani d . 1 1
H H7A 0.9162 0.4203 0.7767 0.060 Uiso calc R 1 1
H H7B 0.7865 0.5112 0.7906 0.060 Uiso calc R 1 1
C C11 0.4282(3) 0.1895(3) 0.4699(3) 0.0433(6) Uani d . 1 1
H H11A 0.4958 0.1617 0.4197 0.052 Uiso calc R 1 1
H H11B 0.3834 0.2735 0.4335 0.052 Uiso calc R 1 1
C C10 0.5040(3) 0.2175(3) 0.6024(3) 0.0458(7) Uani d . 1 1
C C2 0.9219(3) 0.6765(3) 0.4875(3) 0.0483(7) Uani d . 1 1
O O1 0.4794(3) 0.1587(3) 0.6926(2) 0.0607(6) Uani d . 1 1
C C9 0.6086(4) 0.3338(5) 0.6206(3) 0.0700(11) Uani d . 1 1
H H9 0.5568 0.4116 0.6465 0.084 Uiso calc R 1 1
C C8 0.7298(5) 0.3218(5) 0.7187(4) 0.0829(14) Uani d . 1 1
H H8A 0.7849 0.2438 0.7006 0.099 Uiso calc R 1 1
H H8B 0.6999 0.3028 0.7974 0.099 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0554(5) 0.0483(5) 0.0536(5) -0.0019(3) 0.0140(3) -0.0035(3)
O2 0.0478(11) 0.0536(12) 0.0315(9) -0.0070(9) 0.0054(8) 0.0040(8)
F1 0.0627(12) 0.0574(12) 0.0896(15) -0.0171(10) 0.0197(11) -0.0058(11)
C5 0.0363(13) 0.0358(13) 0.0388(14) 0.0062(10) 0.0070(11) -0.0012(10)
C1 0.0396(14) 0.0454(16) 0.0528(16) 0.0045(12) 0.0052(12) -0.0122(13)
C6 0.0376(13) 0.0417(14) 0.0398(14) 0.0112(11) 0.0062(11) -0.0056(11)
C4 0.0409(14) 0.0452(15) 0.0380(14) 0.0029(11) 0.0073(11) -0.0007(11)
C3 0.0486(16) 0.0464(16) 0.0505(16) 0.0062(13) 0.0159(13) 0.0041(13)
C7 0.0517(17) 0.0602(19) 0.0357(14) 0.0038(14) 0.0007(12) -0.0048(13)
C11 0.0477(15) 0.0429(14) 0.0399(14) 0.0034(12) 0.0100(12) 0.0038(11)
C10 0.0455(15) 0.0534(17) 0.0388(14) 0.0048(13) 0.0091(12) 0.0093(12)
C2 0.0417(15) 0.0381(14) 0.067(2) -0.0003(11) 0.0159(14) -0.0067(13)
O1 0.0602(13) 0.0790(16) 0.0427(12) -0.0096(12) 0.0101(10) 0.0160(11)
C9 0.078(2) 0.092(3) 0.0366(16) -0.028(2) 0.0032(15) 0.0125(17)
C8 0.088(3) 0.108(3) 0.0448(19) -0.035(3) -0.0046(18) 0.022(2)
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'
Cl Cl 0.1484 0.1585 '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
C5 O2 C9 115.5(2)
O2 C5 C6 122.7(2)
O2 C5 C4 115.9(2)
C6 C5 C4 121.3(3)
C2 C1 C6 120.1(3)
C2 C1 H1 120.0
C6 C1 H1 120.0
C5 C6 C1 117.7(3)
C5 C6 C7 120.9(3)
C1 C6 C7 121.4(3)
C3 C4 C5 120.1(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C2 C3 C4 118.3(3)
C2 C3 H3 120.8
C4 C3 H3 120.8
C8 C7 C6 111.3(2)
C8 C7 H7A 109.4
C6 C7 H7A 109.4
C8 C7 H7B 109.4
C6 C7 H7B 109.4
H7A C7 H7B 108.0
C10 C11 Cl1 112.2(2)
C10 C11 H11A 109.2
Cl1 C11 H11A 109.2
C10 C11 H11B 109.2
Cl1 C11 H11B 109.2
H11A C11 H11B 107.9
O1 C10 C11 123.6(3)
O1 C10 C9 119.5(3)
C11 C10 C9 116.7(2)
F1 C2 C1 119.0(3)
F1 C2 C3 118.6(3)
C1 C2 C3 122.4(3)
O2 C9 C8 115.8(3)
O2 C9 C10 108.5(3)
C8 C9 C10 118.1(3)
O2 C9 H9 104.2
C8 C9 H9 104.2
C10 C9 H9 104.2
C9 C8 C7 114.2(3)
C9 C8 H8A 108.7
C7 C8 H8A 108.7
C9 C8 H8B 108.7
C7 C8 H8B 108.7
H8A C8 H8B 107.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.761(3)
O2 C5 1.374(3)
O2 C9 1.416(4)
F1 C2 1.354(3)
C5 C6 1.383(4)
C5 C4 1.389(4)
C1 C2 1.364(5)
C1 C6 1.391(4)
C1 H1 0.9300
C6 C7 1.501(4)
C4 C3 1.370(4)
C4 H4 0.9300
C3 C2 1.370(5)
C3 H3 0.9300
C7 C8 1.492(5)
C7 H7A 0.9700
C7 H7B 0.9700
C11 C10 1.497(4)
C11 H11A 0.9700
C11 H11B 0.9700
C10 O1 1.194(4)
C10 C9 1.506(5)
C9 C8 1.420(5)
C9 H9 0.9800
C8 H8A 0.9700
C8 H8B 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
C11 H11B Cg 3_666 0.97 2.76 3.457(3) 129
