#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/58/2015845.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_2015845
loop_
_publ_author_name
'Lotter, A. N. C.'
'Fernandes, M. A.'
'Otterlo, W. A. L. van'
'Koning, C. B. de'
_publ_section_title
;
 1-Benzyl-3,3-dichloro-1H-indol-2(3H)-one
;
_journal_coeditor_code           DN3029
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o157
_journal_page_last               o159
_journal_paper_doi               10.1107/S0108270107002028
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H11 Cl2 N O'
_chemical_formula_moiety         'C15 H11 Cl2 N O'
_chemical_formula_sum            'C15 H11 Cl2 N O'
_chemical_formula_weight         292.15
_chemical_name_systematic
;
1-Benzyl-3,3-dichloro-1H-indol-2(3H)-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                 107.244(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4847(13)
_cell_length_b                   14.4641(18)
_cell_length_c                   9.2203(11)
_cell_measurement_reflns_used    918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.47
_cell_volume                     1335.4(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and SCHAKAL99 (Keller, 1999)
;
_computing_publication_material
;
PLATON (Spek, 2003) and SHELXTL (Bruker, 1999b)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8835
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.350
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.2606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                2603
_reflns_number_total             3213
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3029.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015845
_cod_database_fobs_code          2015845
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
C C1 0.81611(13) 0.08784(10) 0.34296(15) 0.0290(3) Uani d . 1
C C2 0.70179(13) 0.07206(9) 0.41592(15) 0.0277(3) Uani d . 1
C C3 0.65767(13) 0.16757(9) 0.44019(15) 0.0255(3) Uani d . 1
C C4 0.55791(14) 0.19881(10) 0.49812(16) 0.0317(3) Uani d . 1
H H4 0.5008 0.1566 0.5278 0.038 Uiso calc R 1
C C5 0.54361(15) 0.29423(11) 0.51175(17) 0.0353(3) Uani d . 1
H H5 0.4755 0.3175 0.5505 0.042 Uiso calc R 1
C C6 0.62796(14) 0.35510(10) 0.46923(16) 0.0332(3) Uani d . 1
H H6 0.6171 0.4196 0.4806 0.040 Uiso calc R 1
C C7 0.72862(14) 0.32418(9) 0.41007(15) 0.0287(3) Uani d . 1
H H7 0.7857 0.3663 0.3804 0.034 Uiso calc R 1
C C8 0.74163(12) 0.22953(9) 0.39654(14) 0.0242(3) Uani d . 1
C C9 0.93948(14) 0.22510(11) 0.29027(16) 0.0307(3) Uani d . 1
H H9A 0.8999 0.2752 0.2176 0.037 Uiso calc R 1
H H9B 0.9785 0.1789 0.2365 0.037 Uiso calc R 1
C C10 1.04906(13) 0.26494(9) 0.42161(15) 0.0258(3) Uani d . 1
C C11 1.08127(15) 0.35817(10) 0.42543(18) 0.0348(3) Uani d . 1
H H11 1.0333 0.3979 0.3458 0.042 Uiso calc R 1
C C12 1.18380(16) 0.39374(11) 0.5457(2) 0.0432(4) Uani d . 1
H H12 1.2049 0.4577 0.5485 0.052 Uiso calc R 1
C C13 1.25468(15) 0.33616(12) 0.66092(19) 0.0413(4) Uani d . 1
H H13 1.3248 0.3605 0.7425 0.050 Uiso calc R 1
C C14 1.22367(14) 0.24302(12) 0.65765(17) 0.0379(4) Uani d . 1
H H14 1.2728 0.2034 0.7366 0.046 Uiso calc R 1
C C15 1.12072(14) 0.20756(10) 0.53890(16) 0.0305(3) Uani d . 1
H H15 1.0990 0.1437 0.5376 0.037 Uiso calc R 1
N N 0.83419(11) 0.18114(8) 0.34084(13) 0.0264(2) Uani d . 1
O O 0.87652(11) 0.02811(8) 0.29883(14) 0.0436(3) Uani d . 1
Cl Cl1 0.77076(4) 0.01204(3) 0.59136(4) 0.03919(12) Uani d . 1
Cl Cl2 0.57445(4) 0.00267(2) 0.29337(4) 0.03877(12) 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'
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
O C1 N 127.78(13) ?
O C1 C2 125.98(13) ?
N C1 C2 106.23(11) yes
C3 C2 C1 103.98(11) yes
C3 C2 Cl2 114.13(10) ?
C1 C2 Cl2 109.70(9) ?
C3 C2 Cl1 111.92(9) ?
C1 C2 Cl1 107.79(9) ?
Cl2 C2 Cl1 109.04(7) ?
C4 C3 C8 120.99(13) ?
C4 C3 C2 131.50(13) ?
C8 C3 C2 107.49(11) yes
C3 C4 C5 118.07(13) ?
C3 C4 H4 121.0 ?
C5 C4 H4 121.0 ?
C6 C5 C4 120.52(14) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C7 121.79(14) ?
C5 C6 H6 119.1 ?
C7 C6 H6 119.1 ?
C8 C7 C6 117.22(13) ?
C8 C7 H7 121.4 ?
C6 C7 H7 121.4 ?
C7 C8 C3 121.40(12) ?
C7 C8 N 128.30(12) ?
C3 C8 N 110.30(11) yes
N C9 C10 112.05(11) ?
N C9 H9A 109.2 ?
C10 C9 H9A 109.2 ?
N C9 H9B 109.2 ?
C10 C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
C11 C10 C15 119.20(13) ?
C11 C10 C9 120.74(13) ?
C15 C10 C9 120.05(13) ?
C10 C11 C12 120.20(15) ?
C10 C11 H11 119.9 ?
C12 C11 H11 119.9 ?
C13 C12 C11 120.12(15) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C12 C13 C14 120.07(14) ?
C12 C13 H13 120.0 ?
C14 C13 H13 120.0 ?
C13 C14 C15 119.97(15) ?
C13 C14 H14 120.0 ?
C15 C14 H14 120.0 ?
C14 C15 C10 120.44(14) ?
C14 C15 H15 119.8 ?
C10 C15 H15 119.8 ?
C1 N C8 111.85(11) yes
C1 N C9 123.72(12) ?
C8 N C9 124.41(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O 1.2107(17) yes
C1 N 1.3637(18) yes
C1 C2 1.5555(19) yes
C2 C3 1.4945(19) yes
C2 Cl2 1.7811(13) ?
C2 Cl1 1.7888(14) ?
C3 C4 1.3837(19) ?
C3 C8 1.3966(18) yes
C4 C5 1.398(2) ?
C4 H4 0.9500 ?
C5 C6 1.384(2) ?
C5 H5 0.9500 ?
C6 C7 1.397(2) ?
C6 H6 0.9500 ?
C7 C8 1.3851(19) ?
C7 H7 0.9500 ?
C8 N 1.4109(17) yes
C9 N 1.4647(17) ?
C9 C10 1.5145(18) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 C11 1.388(2) ?
C10 C15 1.393(2) ?
C11 C12 1.394(2) ?
C11 H11 0.9500 ?
C12 C13 1.380(2) ?
C12 H12 0.9500 ?
C13 C14 1.384(2) ?
C13 H13 0.9500 ?
C14 C15 1.388(2) ?
C14 H14 0.9500 ?
C15 H15 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
_geom_hbond_publ_flag
C11 H11 O 2_755 0.95 2.64 3.325(2) 129 yes
C9 H9B Cg 4_554 0.99 2.93 3.660(2) 132 yes
C6 H6 Cl2 2_655 0.95 2.98 3.4461(15) 112 yes
C13 H13 Cl1 2_756 0.95 3.01 3.4815(18) 112 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
O C1 C2 C3 -176.71(14)
N C1 C2 C3 3.88(14)
O C1 C2 Cl2 -54.26(18)
N C1 C2 Cl2 126.33(10)
O C1 C2 Cl1 64.35(17)
N C1 C2 Cl1 -115.06(11)
C1 C2 C3 C4 178.48(14)
Cl2 C2 C3 C4 59.00(18)
Cl1 C2 C3 C4 -65.44(17)
C1 C2 C3 C8 -3.51(14)
Cl2 C2 C3 C8 -122.99(10)
Cl1 C2 C3 C8 112.57(11)
C8 C3 C4 C5 0.0(2)
C2 C3 C4 C5 177.77(14)
C3 C4 C5 C6 -0.5(2)
C4 C5 C6 C7 0.7(2)
C5 C6 C7 C8 -0.5(2)
C6 C7 C8 C3 0.00(19)
C6 C7 C8 N 180.00(12)
C4 C3 C8 C7 0.3(2)
C2 C3 C8 C7 -178.01(12)
C4 C3 C8 N -179.75(12)
C2 C3 C8 N 1.99(14)
N C9 C10 C11 -122.02(14)
N C9 C10 C15 59.29(17)
C15 C10 C11 C12 -0.3(2)
C9 C10 C11 C12 -178.97(13)
C10 C11 C12 C13 0.7(2)
C11 C12 C13 C14 -0.3(2)
C12 C13 C14 C15 -0.4(2)
C13 C14 C15 C10 0.8(2)
C11 C10 C15 C14 -0.4(2)
C9 C10 C15 C14 178.28(12)
O C1 N C8 177.71(14)
C2 C1 N C8 -2.90(15)
O C1 N C9 -3.7(2)
C2 C1 N C9 175.65(11)
C7 C8 N C1 -179.33(13)
C3 C8 N C1 0.67(15)
C7 C8 N C9 2.1(2)
C3 C8 N C9 -177.86(12)
C10 C9 N C1 -107.55(15)
C10 C9 N C8 70.82(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133257
