#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/30/2213028.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_2213028
loop_
_publ_author_name
'Hoong-Kun Fun'
'Suchada Chantrapromma'
'Yong-Miao Shen'
'Jian-Hua Xu'
_publ_section_title
4,5,6,7-Tetrachloro-3-(furan-3-yl)-3-hydroxy-2-(3-hydroxypropyl)-2,3-dihydro-1H-isoindol-1-one
_journal_coeditor_code           SJ2264
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2023
_journal_page_last               o2025
_journal_paper_doi               10.1107/S1600536807013736
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C15 H11 Cl4 N O4'
_chemical_formula_sum            'C15 H11 Cl4 N O4'
_chemical_formula_weight         411.05
_chemical_melting_point          467.5(5)
_chemical_name_common
;
4,5,6,7-Tetrachloro-3-furan-3-yl-3-hydroxy-2-(3-hydroxypropyl)-2,3-
dihydroisoindol-1-one
;
_chemical_name_systematic
;
4,5,6,7-Tetrachloro-3-furan-3-yl-3-hydroxy-2-(3-hydroxypropyl)-2,3-
dihydroisoindol-1-one
;
_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                 111.7160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6531(3)
_cell_length_b                   9.8856(2)
_cell_length_c                   15.1278(4)
_cell_measurement_reflns_used    10023
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      40.00
_cell_measurement_theta_min      2.79
_cell_volume                     1619.01(7)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEX2 CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48681
_diffrn_reflns_theta_full        40.00
_diffrn_reflns_theta_max         40.00
_diffrn_reflns_theta_min         2.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.7939
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         10023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.4085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                8567
_reflns_number_total             10023
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj2264.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_chemical_melting_point' value '467-468 K' was changed to '467.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '467-468 K' was changed to '467.5(5)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213028
_cod_database_fobs_code          2213028
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
Cl Cl1 0.096731(18) 0.218790(19) 0.094557(14) 0.01675(4) Uani d . 1
Cl Cl2 0.114774(19) -0.09396(2) 0.123938(14) 0.01836(4) Uani d . 1
Cl Cl3 0.26082(2) -0.269248(19) 0.030224(17) 0.02212(4) Uani d . 1
Cl Cl4 0.396491(19) -0.13045(2) -0.089862(16) 0.02005(4) Uani d . 1
O O1 0.25753(6) 0.42350(6) 0.01794(4) 0.01666(10) Uani d . 1
O O2 0.39701(7) 0.15943(8) -0.16767(5) 0.02229(12) Uani d . 1
O O3 0.04376(6) 0.28663(7) -0.19934(4) 0.01703(10) Uani d . 1
O O4 0.55616(6) 0.67193(7) -0.17043(4) 0.01892(11) Uani d . 1
N N1 0.30181(6) 0.31855(7) -0.10793(5) 0.01447(10) Uani d . 1
C C1 -0.07069(8) 0.33998(10) -0.24951(6) 0.02071(14) Uani d . 1
H H1A -0.1245 0.3077 -0.3079 0.030(4) Uiso calc R 1
C C2 -0.09430(9) 0.44558(10) -0.20249(7) 0.02391(16) Uani d . 1
H H2A -0.1657 0.4979 -0.2217 0.036(4) Uiso calc R 1
C C3 0.01260(8) 0.46122(9) -0.11675(7) 0.02088(14) Uani d . 1
H H3A 0.0247 0.5259 -0.0695 0.042(5) Uiso calc R 1
C C4 0.09203(7) 0.36278(7) -0.11870(5) 0.01356(11) Uani d . 1
C C5 0.22043(7) 0.32570(7) -0.05283(5) 0.01242(10) Uani d . 1
C C6 0.22784(6) 0.17990(7) -0.01803(5) 0.01143(10) Uani d . 1
C C7 0.17521(7) 0.12217(7) 0.04121(5) 0.01227(10) Uani d . 1
C C8 0.18609(7) -0.01823(7) 0.05610(5) 0.01346(10) Uani d . 1
C C9 0.25299(7) -0.09732(7) 0.01475(6) 0.01486(11) Uani d . 1
C C10 0.31060(7) -0.03617(7) -0.04148(5) 0.01418(11) Uani d . 1
C C11 0.29546(7) 0.10191(7) -0.05778(5) 0.01288(10) Uani d . 1
C C12 0.33961(7) 0.19204(8) -0.11750(5) 0.01484(11) Uani d . 1
C C13 0.31028(7) 0.42923(9) -0.16890(6) 0.01756(13) Uani d . 1
H H13A 0.2456 0.4944 -0.1747 0.024(3) Uiso calc R 1
H H13B 0.2959 0.3938 -0.2319 0.021(3) Uiso calc R 1
C C14 0.43430(7) 0.50137(8) -0.13223(6) 0.01650(12) Uani d . 1
H H14A 0.4417 0.5543 -0.0764 0.025(4) Uiso calc R 1
H H14B 0.5005 0.4353 -0.1141 0.026(4) Uiso calc R 1
C C15 0.44533(8) 0.59336(9) -0.20888(6) 0.01737(13) Uani d . 1
H H15A 0.4474 0.5395 -0.2619 0.030(4) Uiso calc R 1
H H15B 0.3743 0.6529 -0.2321 0.019(3) Uiso calc R 1
H H1O4 0.5752(16) 0.6887(18) -0.2175(13) 0.036(4) Uiso d . 1
H H1O1 0.3157(16) 0.3945(18) 0.0638(13) 0.036(4) Uiso 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 O1 H1O1 109.4(13) ?
C4 O3 C1 106.08(7) ?
C15 O4 H1O4 104.2(12) ?
C12 N1 C13 121.72(6) ?
C12 N1 C5 114.03(6) ?
C13 N1 C5 121.93(6) ?
C2 C1 O3 110.62(8) ?
C2 C1 H1A 124.7 ?
O3 C1 H1A 124.7 ?
C1 C2 C3 106.37(8) ?
C1 C2 H2A 126.8 ?
C3 C2 H2A 126.8 ?
C4 C3 C2 105.97(8) ?
C4 C3 H3A 127.0 ?
C2 C3 H3A 127.0 ?
C3 C4 O3 110.95(7) ?
C3 C4 C5 133.06(7) ?
O3 C4 C5 115.95(6) ?
O1 C5 N1 112.75(6) ?
O1 C5 C4 106.91(6) y
N1 C5 C4 109.06(6) y
O1 C5 C6 115.49(6) y
N1 C5 C6 100.56(5) ?
C4 C5 C6 111.98(6) y
C7 C6 C11 120.70(6) ?
C7 C6 C5 129.16(6) ?
C11 C6 C5 110.11(6) ?
C6 C7 C8 118.46(6) ?
C6 C7 Cl1 121.09(5) ?
C8 C7 Cl1 120.45(5) ?
C9 C8 C7 120.73(6) ?
C9 C8 Cl2 119.73(5) ?
C7 C8 Cl2 119.53(6) ?
C10 C9 C8 120.01(6) ?
C10 C9 Cl3 119.85(6) ?
C8 C9 Cl3 120.11(6) ?
C11 C10 C9 118.34(7) ?
C11 C10 Cl4 120.96(6) ?
C9 C10 Cl4 120.70(6) ?
C10 C11 C6 121.66(7) ?
C10 C11 C12 130.30(7) ?
C6 C11 C12 108.01(6) ?
O2 C12 N1 125.72(7) ?
O2 C12 C11 127.46(7) ?
N1 C12 C11 106.81(6) ?
N1 C13 C14 113.51(7) ?
N1 C13 H13A 108.9 ?
C14 C13 H13A 108.9 ?
N1 C13 H13B 108.9 ?
C14 C13 H13B 108.9 ?
H13A C13 H13B 107.7 ?
C15 C14 C13 109.90(6) ?
C15 C14 H14A 109.7 ?
C13 C14 H14A 109.7 ?
C15 C14 H14B 109.7 ?
C13 C14 H14B 109.7 ?
H14A C14 H14B 108.2 ?
O4 C15 C14 109.47(6) ?
O4 C15 H15A 109.8 ?
C14 C15 H15A 109.8 ?
O4 C15 H15B 109.8 ?
C14 C15 H15B 109.8 ?
H15A C15 H15B 108.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C7 1.7164(7) y
Cl2 C8 1.7132(7) y
Cl3 C9 1.7135(7) y
Cl4 C10 1.7170(7) y
O1 C5 1.3876(9) ?
O1 H1O1 0.822(18) ?
O2 C12 1.2261(9) y
O3 C4 1.3651(10) y
O3 C1 1.3725(10) y
O4 C15 1.4332(10) ?
O4 H1O4 0.837(18) ?
N1 C12 1.3514(10) ?
N1 C13 1.4578(10) ?
N1 C5 1.4778(9) ?
C1 C2 1.3476(14) ?
C1 H1A 0.9300 ?
C2 C3 1.4361(13) ?
C2 H2A 0.9300 ?
C3 C4 1.3509(11) ?
C3 H3A 0.9300 ?
C4 C5 1.5043(10) ?
C5 C6 1.5259(9) ?
C6 C7 1.3828(9) ?
C6 C11 1.3883(10) ?
C7 C8 1.4043(10) ?
C8 C9 1.4041(11) ?
C9 C10 1.4008(11) ?
C10 C11 1.3867(10) ?
C11 C12 1.4895(10) ?
C13 C14 1.5204(11) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C15 1.5161(11) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9700 ?
C15 H15B 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 H1O1 O4 3_665 0.822(19) 1.866(19) 2.6868(9) 178(2) y
O4 H1O4 O2 2_654 0.837(19) 1.903(19) 2.7020(10) 159.1(18) y
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
_geom_torsion_publ_flag
C4 O3 C1 C2 -0.16(10) ?
O3 C1 C2 C3 0.35(11) ?
C1 C2 C3 C4 -0.41(11) ?
C2 C3 C4 O3 0.33(10) ?
C2 C3 C4 C5 177.99(8) ?
C1 O3 C4 C3 -0.12(9) ?
C1 O3 C4 C5 -178.22(6) ?
C12 N1 C5 O1 130.69(7) ?
C13 N1 C5 O1 -66.34(9) ?
C12 N1 C5 C4 -110.72(7) ?
C13 N1 C5 C4 52.25(9) ?
C12 N1 C5 C6 7.13(8) ?
C13 N1 C5 C6 170.10(7) ?
C3 C4 C5 O1 -4.40(11) ?
O3 C4 C5 O1 173.17(6) ?
C3 C4 C5 N1 -126.59(9) ?
O3 C4 C5 N1 50.99(8) ?
C3 C4 C5 C6 123.02(9) ?
O3 C4 C5 C6 -59.41(8) ?
O1 C5 C6 C7 55.36(10) ?
N1 C5 C6 C7 177.00(7) ?
C4 C5 C6 C7 -67.31(9) ?
O1 C5 C6 C11 -126.85(7) ?
N1 C5 C6 C11 -5.21(8) ?
C4 C5 C6 C11 110.47(7) ?
C11 C6 C7 C8 -3.38(11) ?
C5 C6 C7 C8 174.20(7) ?
C11 C6 C7 Cl1 177.34(6) ?
C5 C6 C7 Cl1 -5.07(11) ?
C6 C7 C8 C9 2.45(11) ?
Cl1 C7 C8 C9 -178.27(6) ?
C6 C7 C8 Cl2 -176.49(6) ?
Cl1 C7 C8 Cl2 2.79(9) ?
C7 C8 C9 C10 0.50(11) ?
Cl2 C8 C9 C10 179.44(6) ?
C7 C8 C9 Cl3 -177.71(6) ?
Cl2 C8 C9 Cl3 1.23(9) ?
C8 C9 C10 C11 -2.51(11) ?
Cl3 C9 C10 C11 175.71(6) ?
C8 C9 C10 Cl4 178.13(6) ?
Cl3 C9 C10 Cl4 -3.66(9) ?
C9 C10 C11 C6 1.61(11) ?
Cl4 C10 C11 C6 -179.03(6) ?
C9 C10 C11 C12 -176.64(7) ?
Cl4 C10 C11 C12 2.72(12) ?
C7 C6 C11 C10 1.38(11) ?
C5 C6 C11 C10 -176.62(7) ?
C7 C6 C11 C12 179.98(7) ?
C5 C6 C11 C12 1.98(8) ?
C13 N1 C12 O2 9.35(13) ?
C5 N1 C12 O2 172.35(8) ?
C13 N1 C12 C11 -169.31(7) ?
C5 N1 C12 C11 -6.30(9) ?
C10 C11 C12 O2 2.32(14) ?
C6 C11 C12 O2 -176.12(8) ?
C10 C11 C12 N1 -179.06(8) ?
C6 C11 C12 N1 2.50(9) ?
C12 N1 C13 C14 -87.06(10) y
C5 N1 C13 C14 111.28(8) ?
N1 C13 C14 C15 167.92(7) y
C13 C14 C15 O4 173.65(7) y
