#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/08/2210847.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_2210847
loop_
_publ_author_name
'Muhammad Khalid'
'Gul Shahzada Khan'
'Ghulam Qadeer'
'Nasim Hasan Rama'
'Wong, Wai-Yeung'
_publ_section_title
;
 3-(2-Chloro-4-fluorophenyl)-1H-isochromen-1-one
;
_journal_coeditor_code           YM2022
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4539
_journal_page_last               o4540
_journal_paper_doi               10.1107/S1600536806035999
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H8 Cl F O2'
_chemical_formula_moiety         'C15 H8 Cl F O2'
_chemical_formula_sum            'C15 H8 Cl F O2'
_chemical_formula_weight         274.66
_chemical_melting_point          437
_chemical_name_common            3-(2-Chloro-4-fluorophenyl)isocoumarin
_chemical_name_systematic
;
3-(2-Chloro-4-fluorophenyl)-1H-isochromen-1-one
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4621(4)
_cell_length_b                   12.1011(6)
_cell_length_c                   13.2757(7)
_cell_measurement_reflns_used    5893
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      0.996
_cell_volume                     1198.79(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5893
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.025
_refine_ls_R_factor_gt           0.025
_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)+(0.0439P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.069
_refine_ls_wR_factor_ref         0.069
_reflns_number_gt                2047
_reflns_number_total             2097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ym2022.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2210847
_cod_database_fobs_code          2210847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
C C1 0.70664(19) 0.42504(12) 0.61108(12) 0.0406(3) Uani d . 1
C C2 0.65150(19) 0.36557(12) 0.70145(11) 0.0380(3) Uani d . 1
C C3 0.6676(2) 0.41550(14) 0.79581(12) 0.0477(4) Uani d . 1
H H3A 0.7135 0.4867 0.8009 0.057 Uiso calc R 1
C C4 0.6160(3) 0.36005(16) 0.88099(13) 0.0573(4) Uani d . 1
H H4A 0.6275 0.3934 0.9438 0.069 Uiso calc R 1
C C5 0.5465(3) 0.25383(16) 0.87321(13) 0.0578(4) Uani d . 1
H H5A 0.5097 0.2168 0.9310 0.069 Uiso calc R 1
C C6 0.5314(2) 0.20286(14) 0.78123(12) 0.0489(4) Uani d . 1
H H6A 0.4860 0.1314 0.7775 0.059 Uiso calc R 1
C C7 0.58378(19) 0.25719(12) 0.69321(11) 0.0379(3) Uani d . 1
C C8 0.5718(2) 0.20861(12) 0.59468(11) 0.0390(3) Uani d . 1
H H8A 0.5262 0.1375 0.5879 0.047 Uiso calc R 1
C C9 0.62468(19) 0.26323(11) 0.51316(11) 0.0355(3) Uani d . 1
C C10 0.61645(19) 0.22891(12) 0.40656(11) 0.0368(3) Uani d . 1
C C11 0.66687(19) 0.12400(13) 0.37256(11) 0.0415(3) Uani d . 1
C C12 0.6589(2) 0.09617(15) 0.27105(12) 0.0498(4) Uani d . 1
H H12A 0.6927 0.0263 0.2489 0.060 Uiso calc R 1
C C13 0.5997(2) 0.17474(16) 0.20449(12) 0.0525(4) Uani d . 1
C C14 0.5485(2) 0.27887(16) 0.23293(12) 0.0523(4) Uani d . 1
H H14A 0.5086 0.3302 0.1859 0.063 Uiso calc R 1
C C15 0.5586(2) 0.30474(13) 0.33441(12) 0.0447(4) Uani d . 1
H H15A 0.5255 0.3752 0.3552 0.054 Uiso calc R 1
Cl Cl1 0.75024(6) 0.02413(3) 0.45334(3) 0.05804(15) Uani d . 1
F F1 0.59309(18) 0.14675(12) 0.10590(7) 0.0816(4) Uani d . 1
O O1 0.76406(18) 0.51787(9) 0.60817(10) 0.0587(3) Uani d . 1
O O2 0.69109(13) 0.37064(8) 0.52035(7) 0.0403(2) 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 0.0033 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 116.63(14)
O1 C1 C2 126.00(14)
O2 C1 C2 117.37(12)
C3 C2 C7 120.21(14)
C3 C2 C1 120.02(14)
C7 C2 C1 119.76(13)
C4 C3 C2 120.30(15)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C3 C4 C5 119.76(15)
C3 C4 H4A 120.1
C5 C4 H4A 120.1
C6 C5 C4 120.81(16)
C6 C5 H5A 119.6
C4 C5 H5A 119.6
C5 C6 C7 120.66(16)
C5 C6 H6A 119.7
C7 C6 H6A 119.7
C6 C7 C2 118.25(14)
C6 C7 C8 123.49(13)
C2 C7 C8 118.26(13)
C9 C8 C7 121.32(12)
C9 C8 H8A 119.3
C7 C8 H8A 119.3
C8 C9 O2 120.91(12)
C8 C9 C10 128.97(13)
O2 C9 C10 110.04(12)
C15 C10 C11 117.31(13)
C15 C10 C9 119.08(13)
C11 C10 C9 123.60(14)
C12 C11 C10 121.40(15)
C12 C11 Cl1 116.53(13)
C10 C11 Cl1 122.03(11)
C13 C12 C11 118.07(16)
C13 C12 H12A 121.0
C11 C12 H12A 121.0
F1 C13 C14 119.14(17)
F1 C13 C12 117.49(17)
C14 C13 C12 123.37(15)
C13 C14 C15 117.45(16)
C13 C14 H14A 121.3
C15 C14 H14A 121.3
C14 C15 C10 122.40(16)
C14 C15 H15A 118.8
C10 C15 H15A 118.8
C1 O2 C9 122.37(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2029(19)
C1 O2 1.3776(17)
C1 C2 1.458(2)
C2 C3 1.396(2)
C2 C7 1.410(2)
C3 C4 1.370(3)
C3 H3A 0.9300
C4 C5 1.390(3)
C4 H4A 0.9300
C5 C6 1.373(2)
C5 H5A 0.9300
C6 C7 1.396(2)
C6 H6A 0.9300
C7 C8 1.437(2)
C8 C9 1.328(2)
C8 H8A 0.9300
C9 O2 1.3943(17)
C9 C10 1.476(2)
C10 C15 1.395(2)
C10 C11 1.399(2)
C11 C12 1.390(2)
C11 Cl1 1.7314(16)
C12 C13 1.371(3)
C12 H12A 0.9300
C13 F1 1.3529(18)
C13 C14 1.370(3)
C14 C15 1.385(2)
C14 H14A 0.9300
C15 H15A 0.9300
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
C8 H8A Cl1 1_555 0.93 2.81 3.2059(15) 107 yes
C4 H4A O1 2_665 0.93 2.56 3.476(2) 167 yes
C5 H5A F1 1_556 0.93 2.55 3.368(2) 147 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
O1 C1 C2 C3 -1.7(2)
O2 C1 C2 C3 178.67(13)
O1 C1 C2 C7 179.00(16)
O2 C1 C2 C7 -0.7(2)
C7 C2 C3 C4 -0.7(2)
C1 C2 C3 C4 180.00(15)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 1.1(3)
C4 C5 C6 C7 -0.8(3)
C5 C6 C7 C2 -0.3(2)
C5 C6 C7 C8 179.91(16)
C3 C2 C7 C6 1.0(2)
C1 C2 C7 C6 -179.70(14)
C3 C2 C7 C8 -179.19(13)
C1 C2 C7 C8 0.1(2)
C6 C7 C8 C9 -179.44(15)
C2 C7 C8 C9 0.7(2)
C7 C8 C9 O2 -1.0(2)
C7 C8 C9 C10 -177.47(14)
C8 C9 C10 C15 136.07(17)
O2 C9 C10 C15 -40.66(18)
C8 C9 C10 C11 -45.1(2)
O2 C9 C10 C11 138.15(15)
C15 C10 C11 C12 -0.3(2)
C9 C10 C11 C12 -179.13(14)
C15 C10 C11 Cl1 177.17(11)
C9 C10 C11 Cl1 -1.7(2)
C10 C11 C12 C13 -0.1(2)
Cl1 C11 C12 C13 -177.66(13)
C11 C12 C13 F1 179.78(15)
C11 C12 C13 C14 0.1(3)
F1 C13 C14 C15 -179.46(15)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C10 -0.6(3)
C11 C10 C15 C14 0.6(2)
C9 C10 C15 C14 179.52(14)
O1 C1 O2 C9 -179.31(15)
C2 C1 O2 C9 0.37(19)
C8 C9 O2 C1 0.5(2)
C10 C9 O2 C1 177.52(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127098
