#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200877.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_2200877
loop_
_publ_author_name
'Anwar Usman'
'Ibrahim Abdul Razak'
'Hoong-Kun Fun'
'Suchada Chantrapromma'
'Yan Zhang'
'Jian-Hua Xu'
_publ_section_title
1-Acetyl-3-(2-chloro-2,3-dihydrobenzofuran-3-yl)-1,2-dihydro-3-hydroxy-2-oxo-3H-indole
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o37
_journal_page_last               o39
_journal_paper_doi               10.1107/S1600536801020943
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C18 H14 Cl N O4'
_chemical_formula_moiety         'C18 H14 Cl N O4'
_chemical_formula_sum            'C18 H14 Cl N O4'
_chemical_formula_weight         343.75
_chemical_melting_point          406
_chemical_name_systematic
;
1-Acetyl-1,2-dihydro-2-oxo-3-hydroxy-3-(2-chloro-2,3-
dihydrobenzofuran-3-yl)-(3H)indole
;
_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                109.5410(10)
_cell_angle_beta                 97.2270(10)
_cell_angle_gamma                104.4270(10)
_cell_formula_units_Z            2
_cell_length_a                   7.86750(10)
_cell_length_b                   9.0796(2)
_cell_length_c                   12.4097(2)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.79
_cell_volume                     787.54(3)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .971
_diffrn_measured_fraction_theta_max .971
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .068
_diffrn_reflns_av_sigmaI/netI    .1459
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5179
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .265
_exptl_absorpt_correction_T_max  .964
_exptl_absorpt_correction_T_min  .883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_refine_diff_density_max         .41
_refine_diff_density_min         -.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .92
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .92
_refine_ls_R_factor_all          .095
_refine_ls_R_factor_gt           .072
_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)+(0.0688P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .174
_refine_ls_wR_factor_ref         .194
_reflns_number_gt                2171
_reflns_number_total             3338
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6088.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:

'_chemical_melting_point' value '406K' was changed to '406' - the
value should be numeric and without a unit designator.

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 '406K' was changed to '406' - the
value should be numeric and without a unit
designator.

'_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_original_cell_volume        787.54(2)
_cod_database_code               2200877
_cod_database_fobs_code          2200877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 .15018(10) .45538(11) .18958(8) .0527(3) Uani d . 1 . . Cl
O1 1.2326(3) .9055(4) .2714(2) .0627(7) Uani d . 1 . . O
O2 .7094(3) .9129(3) .1841(2) .0551(7) Uani d . 1 . . O
O3 .5619(3) .8896(3) .3883(2) .0443(6) Uani d . 1 . . O
H3B .483(5) .885(4) .341(3) .040(10) Uiso d . 1 . . H
O4 .4294(3) .4021(3) .29140(18) .0428(5) Uani d . 1 . . O
N1 .9435(3) .8656(3) .2887(2) .0310(5) Uani d . 1 . . N
C1 .7844(3) .7563(3) .4039(2) .0296(6) Uani d . 1 . . C
C2 .7651(4) .7039(4) .4943(3) .0431(7) Uani d . 1 . . C
H2A .6532 .6774 .5125 .052 Uiso calc R 1 . . H
C3 .9147(5) .6907(4) .5588(3) .0526(9) Uani d . 1 . . C
H3A .9022 .6508 .6182 .063 Uiso calc R 1 . . H
C4 1.0811(4) .7368(4) .5342(3) .0480(8) Uani d . 1 . . C
H4A 1.1800 .7275 .5780 .058 Uiso calc R 1 . . H
C5 1.1059(4) .7965(3) .4468(2) .0368(7) Uani d . 1 . . C
H5A 1.2197 .8309 .4328 .044 Uiso calc R 1 . . H
C6 .9552(4) .8031(3) .3808(2) .0285(6) Uani d . 1 . . C
C7 .7660(4) .8651(3) .2562(3) .0332(6) Uani d . 1 . . C
C8 .6484(3) .7825(3) .3225(2) .0311(6) Uani d . 1 . . C
C9 1.0879(4) .9188(4) .2399(3) .0377(7) Uani d . 1 . . C
C10 1.0544(5) .9821(5) .1469(3) .0571(9) Uani d . 1 . . C
H10A .9487 .9067 .0882 .086 Uiso calc R 1 . . H
H10B 1.1562 .9935 .1116 .086 Uiso calc R 1 . . H
H10C 1.0365 1.0874 .1804 .086 Uiso calc R 1 . . H
C11 .5070(3) .6266(3) .2298(2) .0296(6) Uani d . 1 . . C
H11A .4407 .6557 .1718 .036 Uiso calc R 1 . . H
C12 .5808(4) .4907(3) .1676(2) .0317(6) Uani d . 1 . . C
C13 .6819(4) .4727(4) .0829(2) .0372(7) Uani d . 1 . . C
H13A .7168 .5546 .0536 .045 Uiso calc R 1 . . H
C14 .7301(4) .3299(4) .0427(3) .0486(8) Uani d . 1 . . C
H14A .7975 .3155 -.0143 .058 Uiso calc R 1 . . H
C15 .6785(5) .2109(4) .0866(3) .0525(9) Uani d . 1 . . C
H15A .7122 .1163 .0588 .063 Uiso calc R 1 . . H
C16 .5778(5) .2260(4) .1712(3) .0501(9) Uani d . 1 . . C
H16A .5433 .1444 .2008 .060 Uiso calc R 1 . . H
C17 .5315(4) .3680(4) .2091(3) .0373(7) Uani d . 1 . . C
C18 .3736(4) .5357(4) .2845(3) .0375(7) Uani d . 1 . . C
H18A .3734 .6096 .3628 .045 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
C8 O3 H3B 104(3) ?
C17 O4 C18 106.7(2) ?
C7 N1 C9 126.0(2) ?
C7 N1 C6 108.9(2) ?
C9 N1 C6 125.2(2) ?
C2 C1 C6 119.8(3) ?
C2 C1 C8 130.1(3) ?
C6 C1 C8 110.0(2) ?
C1 C2 C3 119.3(3) ?
C1 C2 H2A 120.3 ?
C3 C2 H2A 120.3 ?
C4 C3 C2 119.8(3) ?
C4 C3 H3A 120.1 ?
C2 C3 H3A 120.1 ?
C3 C4 C5 122.1(3) ?
C3 C4 H4A 118.9 ?
C5 C4 H4A 118.9 ?
C4 C5 C6 117.4(3) ?
C4 C5 H5A 121.3 ?
C6 C5 H5A 121.3 ?
C5 C6 C1 121.5(2) ?
C5 C6 N1 128.9(2) ?
C1 C6 N1 109.5(2) ?
O2 C7 N1 126.7(3) ?
O2 C7 C8 124.2(2) ?
N1 C7 C8 109.0(2) ?
O3 C8 C1 109.9(2) ?
O3 C8 C7 110.7(2) yes
C1 C8 C7 102.3(2) yes
O3 C8 C11 110.1(2) yes
C1 C8 C11 116.3(2) ?
C7 C8 C11 107.0(2) ?
O1 C9 N1 119.6(3) ?
O1 C9 C10 121.7(3) ?
N1 C9 C10 118.6(3) ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C12 C11 C18 100.0(2) ?
C12 C11 C8 115.1(2) yes
C18 C11 C8 112.4(2) yes
C12 C11 H11A 109.7 ?
C18 C11 H11A 109.7 ?
C8 C11 H11A 109.7 ?
C17 C12 C13 119.3(3) ?
C17 C12 C11 108.1(2) ?
C13 C12 C11 132.6(3) ?
C12 C13 C14 118.7(3) ?
C12 C13 H13A 120.6 ?
C14 C13 H13A 120.6 ?
C15 C14 C13 120.1(3) ?
C15 C14 H14A 120.0 ?
C13 C14 H14A 120.0 ?
C14 C15 C16 122.3(3) ?
C14 C15 H15A 118.9 ?
C16 C15 H15A 118.9 ?
C17 C16 C15 116.5(3) ?
C17 C16 H16A 121.8 ?
C15 C16 H16A 121.8 ?
C12 C17 C16 123.1(3) ?
C12 C17 O4 112.7(3) ?
C16 C17 O4 124.2(3) ?
O4 C18 C11 107.3(2) ?
O4 C18 Cl1 108.53(19) yes
C11 C18 Cl1 109.52(19) yes
O4 C18 H18A 110.5 ?
C11 C18 H18A 110.5 ?
Cl1 C18 H18A 110.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 . 1.810(3) yes
O1 C9 . 1.204(4) ?
O2 C7 . 1.201(3) ?
O3 C8 . 1.419(3) yes
O3 H3B . .78(3) ?
O4 C17 . 1.380(4) yes
O4 C18 . 1.413(3) yes
N1 C7 . 1.403(4) ?
N1 C9 . 1.409(3) ?
N1 C6 . 1.438(3) ?
C1 C2 . 1.369(4) ?
C1 C6 . 1.401(4) ?
C1 C8 . 1.495(4) yes
C2 C3 . 1.391(5) ?
C2 H2A . .93 ?
C3 C4 . 1.377(5) ?
C3 H3A . .93 ?
C4 C5 . 1.379(4) ?
C4 H4A . .93 ?
C5 C6 . 1.380(4) ?
C5 H5A . .93 ?
C7 C8 . 1.534(4) yes
C8 C11 . 1.540(4) yes
C9 C10 . 1.475(4) ?
C10 H10A . .96 ?
C10 H10B . .96 ?
C10 H10C . .96 ?
C11 C12 . 1.513(4) yes
C11 C18 . 1.538(4) yes
C11 H11A . .98 ?
C12 C17 . 1.370(4) ?
C12 C13 . 1.387(4) ?
C13 C14 . 1.391(4) ?
C13 H13A . .93 ?
C14 C15 . 1.364(5) ?
C14 H14A . .93 ?
C15 C16 . 1.384(5) ?
C15 H15A . .93 ?
C16 C17 . 1.373(4) ?
C16 H16A . .93 ?
C18 H18A . .98 ?
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
C6 C1 C2 C3 -3.0(4) ?
C8 C1 C2 C3 -179.4(3) ?
C1 C2 C3 C4 2.7(5) ?
C2 C3 C4 C5 -.1(5) ?
C3 C4 C5 C6 -2.3(5) ?
C4 C5 C6 C1 2.0(4) ?
C4 C5 C6 N1 177.1(3) ?
C2 C1 C6 C5 .6(4) ?
C8 C1 C6 C5 177.7(2) ?
C2 C1 C6 N1 -175.4(2) ?
C8 C1 C6 N1 1.7(3) ?
C7 N1 C6 C5 -173.1(3) ?
C9 N1 C6 C5 6.8(4) ?
C7 N1 C6 C1 2.4(3) ?
C9 N1 C6 C1 -177.7(2) ?
C9 N1 C7 O2 -1.8(5) ?
C6 N1 C7 O2 178.0(3) ?
C9 N1 C7 C8 174.6(2) ?
C6 N1 C7 C8 -5.5(3) ?
C2 C1 C8 O3 54.3(4) ?
C6 C1 C8 O3 -122.4(2) ?
C2 C1 C8 C7 172.0(3) ?
C6 C1 C8 C7 -4.8(3) ?
C2 C1 C8 C11 -71.8(4) ?
C6 C1 C8 C11 111.5(3) ?
O2 C7 C8 O3 -60.1(4) ?
N1 C7 C8 O3 123.3(2) ?
O2 C7 C8 C1 -177.2(3) ?
N1 C7 C8 C1 6.2(3) ?
O2 C7 C8 C11 60.0(4) ?
N1 C7 C8 C11 -116.6(2) ?
C7 N1 C9 O1 -176.3(3) yes
C6 N1 C9 O1 3.8(4) yes
C7 N1 C9 C10 .8(4) ?
C6 N1 C9 C10 -179.1(3) ?
O3 C8 C11 C12 -170.4(2) ?
C1 C8 C11 C12 -44.5(3) ?
C7 C8 C11 C12 69.1(3) ?
O3 C8 C11 C18 -56.8(3) ?
C1 C8 C11 C18 69.1(3) ?
C7 C8 C11 C18 -177.3(2) ?
C18 C11 C12 C17 -13.9(3) ?
C8 C11 C12 C17 106.8(3) ?
C18 C11 C12 C13 166.3(3) ?
C8 C11 C12 C13 -73.1(4) ?
C17 C12 C13 C14 .0(4) ?
C11 C12 C13 C14 179.9(3) ?
C12 C13 C14 C15 -.2(4) ?
C13 C14 C15 C16 .1(5) ?
C14 C15 C16 C17 .1(5) ?
C13 C12 C17 C16 .2(4) ?
C11 C12 C17 C16 -179.7(3) ?
C13 C12 C17 O4 -179.1(2) ?
C11 C12 C17 O4 1.1(3) ?
C15 C16 C17 C12 -.3(5) ?
C15 C16 C17 O4 178.9(3) ?
C18 O4 C17 C12 13.8(3) ?
C18 O4 C17 C16 -165.4(3) ?
C17 O4 C18 C11 -22.6(3) ?
C17 O4 C18 Cl1 95.7(2) ?
C12 C11 C18 O4 22.0(3) ?
C8 C11 C18 O4 -100.5(3) ?
C12 C11 C18 Cl1 -95.6(2) ?
C8 C11 C18 Cl1 141.9(2) ?
