#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/29/2212994.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_2212994
loop_
_publ_author_name
'Saeed, Aamer'
'Bolte, Michael'
_publ_section_title
;
 3-(4-Chlorophenyl)isocoumarin
;
_journal_coeditor_code           SG2143
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1667
_journal_page_last               o1668
_journal_paper_doi               10.1107/S1600536807009890
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H9 Cl O2'
_chemical_formula_moiety         'C15 H9 Cl O2'
_chemical_formula_sum            'C15 H9 Cl O2'
_chemical_formula_weight         256.67
_chemical_name_systematic
;
3-(4-Chlorophenyl)isocoumarin
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.211(8)
_cell_angle_beta                 104.611(9)
_cell_angle_gamma                109.701(9)
_cell_formula_units_Z            2
_cell_length_a                   7.0616(8)
_cell_length_b                   7.2258(8)
_cell_length_c                   13.0949(14)
_cell_measurement_reflns_used    7247
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      3.6
_cell_volume                     594.87(13)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics
'PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_diffrn_measurement_method       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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7741
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0337
_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)+(0.0517P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2052
_reflns_number_total             2406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2143.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2212994
_cod_database_fobs_code          2212994
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.25415(7) 1.07493(6) 0.93710(3) 0.05134(15) Uani d . 1
O O1 0.25237(13) 0.53626(12) 0.49014(7) 0.0288(2) Uani d . 1
O O2 0.27623(15) 0.26925(13) 0.40324(8) 0.0374(2) Uani d . 1
C C2 0.26261(18) 0.43137(17) 0.39855(11) 0.0284(3) Uani d . 1
C C3 0.25370(18) 0.52358(17) 0.30390(11) 0.0278(3) Uani d . 1
C C4 0.2597(2) 0.42292(19) 0.20814(12) 0.0363(3) Uani d . 1
H H4 0.2751 0.2970 0.2051 0.044 Uiso calc R 1
C C5 0.2434(2) 0.5066(2) 0.11769(12) 0.0418(3) Uani d . 1
H H5 0.2480 0.4387 0.0526 0.050 Uiso calc R 1
C C6 0.2199(2) 0.6927(2) 0.12257(12) 0.0394(3) Uani d . 1
H H6 0.2069 0.7493 0.0602 0.047 Uiso calc R 1
C C7 0.2155(2) 0.79405(19) 0.21670(11) 0.0328(3) Uani d . 1
H H7 0.2004 0.9201 0.2188 0.039 Uiso calc R 1
C C8 0.23311(18) 0.71198(17) 0.30992(10) 0.0266(3) Uani d . 1
C C9 0.23342(18) 0.81307(17) 0.41085(10) 0.0275(3) Uani d . 1
H H9 0.2255 0.9423 0.4166 0.033 Uiso calc R 1
C C10 0.24476(18) 0.72726(17) 0.49692(10) 0.0255(3) Uani d . 1
C C11 0.25097(18) 0.81282(17) 0.60560(10) 0.0266(3) Uani d . 1
C C12 0.2322(2) 1.00081(19) 0.62652(10) 0.0300(3) Uani d . 1
H H12 0.2182 1.0731 0.5705 0.036 Uiso calc R 1
C C13 0.2340(2) 1.08046(19) 0.72787(11) 0.0337(3) Uani d . 1
H H13 0.2207 1.2066 0.7414 0.040 Uiso calc R 1
C C14 0.2553(2) 0.9742(2) 0.80978(11) 0.0346(3) Uani d . 1
C C15 0.2764(2) 0.7903(2) 0.79211(11) 0.0363(3) Uani d . 1
H H15 0.2922 0.7199 0.8489 0.044 Uiso calc R 1
C C16 0.2741(2) 0.71053(19) 0.69019(11) 0.0323(3) Uani d . 1
H H16 0.2883 0.5847 0.6776 0.039 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C10 122.60(10)
O2 C2 O1 116.82(12)
O2 C2 C3 125.72(12)
O1 C2 C3 117.46(10)
C4 C3 C8 120.64(12)
C4 C3 C2 120.10(11)
C8 C3 C2 119.24(12)
C5 C4 C3 120.04(12)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 119.68(13)
C4 C5 H5 120.2
C6 C5 H5 120.2
C7 C6 C5 120.80(13)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C8 120.42(12)
C6 C7 H7 119.8
C8 C7 H7 119.8
C7 C8 C3 118.41(12)
C7 C8 C9 122.73(11)
C3 C8 C9 118.86(11)
C10 C9 C8 120.85(10)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 O1 120.80(11)
C9 C10 C11 127.22(11)
O1 C10 C11 111.97(11)
C16 C11 C12 118.47(12)
C16 C11 C10 121.28(11)
C12 C11 C10 120.25(11)
C13 C12 C11 120.59(12)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 119.46(12)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 121.32(13)
C15 C14 Cl1 119.62(11)
C13 C14 Cl1 119.06(10)
C14 C15 C16 119.05(13)
C14 C15 H15 120.5
C16 C15 H15 120.5
C15 C16 C11 121.09(12)
C15 C16 H16 119.5
C11 C16 H16 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.7487(14)
O1 C2 1.3791(16)
O1 C10 1.3933(14)
O2 C2 1.2140(15)
C2 C3 1.4670(18)
C3 C4 1.3978(19)
C3 C8 1.4130(16)
C4 C5 1.384(2)
C4 H4 0.9500
C5 C6 1.406(2)
C5 H5 0.9500
C6 C7 1.377(2)
C6 H6 0.9500
C7 C8 1.4098(17)
C7 H7 0.9500
C8 C9 1.4383(18)
C9 C10 1.3418(18)
C9 H9 0.9500
C10 C11 1.4729(18)
C11 C16 1.4026(17)
C11 C12 1.4132(17)
C12 C13 1.3835(19)
C12 H12 0.9500
C13 C14 1.392(2)
C13 H13 0.9500
C14 C15 1.388(2)
C15 C16 1.389(2)
C15 H15 0.9500
C16 H16 0.9500
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
C9 H9 O2 1_565 0.95 2.30 3.2220(14) 163.3
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
C10 O1 C2 O2 177.43(10)
C10 O1 C2 C3 -3.25(15)
O2 C2 C3 C4 0.34(19)
O1 C2 C3 C4 -178.91(10)
O2 C2 C3 C8 178.60(12)
O1 C2 C3 C8 -0.65(16)
C8 C3 C4 C5 -0.65(19)
C2 C3 C4 C5 177.59(12)
C3 C4 C5 C6 -0.2(2)
C4 C5 C6 C7 0.8(2)
C5 C6 C7 C8 -0.4(2)
C6 C7 C8 C3 -0.47(19)
C6 C7 C8 C9 178.80(12)
C4 C3 C8 C7 1.00(18)
C2 C3 C8 C7 -177.25(10)
C4 C3 C8 C9 -178.30(11)
C2 C3 C8 C9 3.45(17)
C7 C8 C9 C10 178.17(11)
C3 C8 C9 C10 -2.56(18)
C8 C9 C10 O1 -1.26(18)
C8 C9 C10 C11 178.67(10)
C2 O1 C10 C9 4.31(17)
C2 O1 C10 C11 -175.63(9)
C9 C10 C11 C16 -176.62(12)
O1 C10 C11 C16 3.32(16)
C9 C10 C11 C12 3.79(19)
O1 C10 C11 C12 -176.27(10)
C16 C11 C12 C13 -0.79(18)
C10 C11 C12 C13 178.81(11)
C11 C12 C13 C14 0.3(2)
C12 C13 C14 C15 0.5(2)
C12 C13 C14 Cl1 -179.22(10)
C13 C14 C15 C16 -0.6(2)
Cl1 C14 C15 C16 179.08(10)
C14 C15 C16 C11 0.0(2)
C12 C11 C16 C15 0.64(19)
C10 C11 C16 C15 -178.95(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124957
