#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/64/2226405.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_2226405
loop_
_publ_author_name
'Yang, Xue-Mei'
_publ_section_title
;
 (RS)-1-(1-Acetylindolin-5-yl)-2-chloropropan-1-one
;
_journal_coeditor_code           DN2565
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1617
_journal_paper_doi               10.1107/S1600536810020969
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 Cl N O2'
_chemical_formula_moiety         'C13 H14 Cl N O2'
_chemical_formula_sum            'C13 H14 Cl N O2'
_chemical_formula_weight         251.70
_chemical_name_systematic
;
(RS)-1-(1-Acetylindolin-5-yl)-2-chloropropan-1-one
;
_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                112.0710(10)
_cell_angle_beta                 110.3450(10)
_cell_angle_gamma                99.9130(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4748(5)
_cell_length_b                   9.0928(5)
_cell_length_c                   9.4952(5)
_cell_measurement_reflns_used    4108
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.58
_cell_volume                     595.92(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD 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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6682
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_correction_T_min  0.8709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0427
_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)+(0.0322P)²+0.3925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2242
_reflns_number_total             2594
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2565.cif
_cod_data_source_block           I
_cod_database_code               2226405
_cod_database_fobs_code          2226405
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9779(2) -0.01243(19) 0.2587(2) 0.0410(4) Uani d . 1 . .
O O2 0.35372(18) 0.39091(17) 0.09272(18) 0.0348(3) Uani d . 1 . .
N N1 0.7298(2) -0.10127(19) 0.28713(19) 0.0271(3) Uani d . 1 . .
C C1 0.6190(3) -0.2154(3) 0.3214(3) 0.0394(5) Uani d . 1 . .
H H1A 0.6802 -0.1916 0.4415 0.047 Uiso calc R 1 . .
H H1B 0.5956 -0.3354 0.2463 0.047 Uiso calc R 1 . .
C C2 0.4441(3) -0.1788(2) 0.2847(3) 0.0323(4) Uani d . 1 . .
H H2A 0.3427 -0.2765 0.1824 0.039 Uiso calc R 1 . .
H H2B 0.4166 -0.1526 0.3827 0.039 Uiso calc R 1 . .
C C3 0.4790(2) -0.0270(2) 0.2553(2) 0.0252(4) Uani d . 1 . .
C C4 0.3712(2) 0.0667(2) 0.2265(2) 0.0253(4) Uani d . 1 . .
H H4 0.2594 0.0427 0.2300 0.030 Uiso calc R 1 . .
C C5 0.4281(2) 0.1977(2) 0.1918(2) 0.0249(4) Uani d . 1 . .
C C6 0.5941(2) 0.2322(2) 0.1900(2) 0.0279(4) Uani d . 1 . .
H H6 0.6319 0.3208 0.1661 0.033 Uiso calc R 1 . .
C C7 0.7055(2) 0.1416(2) 0.2219(2) 0.0292(4) Uani d . 1 . .
H H7 0.8188 0.1677 0.2217 0.035 Uiso calc R 1 . .
C C8 0.6455(2) 0.0109(2) 0.2544(2) 0.0245(4) Uani d . 1 . .
C C9 0.8883(2) -0.1095(2) 0.2860(2) 0.0296(4) Uani d . 1 . .
C C10 0.9462(3) -0.2455(3) 0.3189(3) 0.0358(4) Uani d . 1 . .
H H10A 0.8635 -0.3568 0.2239 0.054 Uiso calc R 1 . .
H H10B 0.9452 -0.2369 0.4246 0.054 Uiso calc R 1 . .
H H10C 1.0679 -0.2313 0.3298 0.054 Uiso calc R 1 . .
C C11 0.3175(2) 0.3004(2) 0.1525(2) 0.0264(4) Uani d . 1 A .
C C12 0.1597(3) 0.2956(2) 0.1952(2) 0.0306(4) Uani d D 1 . .
H H12 0.1025 0.1787 0.1740 0.037 Uiso d R 1 A .
C C13 0.0115(16) 0.3460(17) 0.0833(16) 0.058(4) Uani d PD 0.60 A 1
H H13A -0.0826 0.3497 0.1206 0.087 Uiso calc PR 0.60 A 1
H H13B -0.0414 0.2617 -0.0370 0.087 Uiso calc PR 0.60 A 1
H H13C 0.0678 0.4576 0.0975 0.087 Uiso calc PR 0.60 A 1
Cl Cl1 0.2419(3) 0.4356(3) 0.40972(18) 0.0464(6) Uani d PD 0.60 A 1
C C13B 0.244(2) 0.4216(19) 0.4003(16) 0.072(6) Uani d PD 0.40 A 2
H H13D 0.3329 0.3851 0.4631 0.108 Uiso calc PR 0.40 A 2
H H13E 0.1470 0.4173 0.4347 0.108 Uiso calc PR 0.40 A 2
H H13F 0.3008 0.5379 0.4258 0.108 Uiso calc PR 0.40 A 2
Cl Cl1B 0.0086(5) 0.3588(5) 0.0840(4) 0.0361(9) Uani d PD 0.40 A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N1 C8 . . 126.44(15) ?
C9 N1 C1 . . 123.37(15) ?
C8 N1 C1 . . 110.18(14) ?
N1 C1 C2 . . 105.33(15) ?
N1 C1 H1A . . 110.7 ?
C2 C1 H1A . . 110.7 ?
N1 C1 H1B . . 110.7 ?
C2 C1 H1B . . 110.7 ?
H1A C1 H1B . . 108.8 ?
C3 C2 C1 . . 104.15(15) ?
C3 C2 H2A . . 110.9 ?
C1 C2 H2A . . 110.9 ?
C3 C2 H2B . . 110.9 ?
C1 C2 H2B . . 110.9 ?
H2A C2 H2B . . 108.9 ?
C4 C3 C8 . . 120.43(16) ?
C4 C3 C2 . . 129.55(16) ?
C8 C3 C2 . . 109.99(15) ?
C3 C4 C5 . . 119.36(16) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 119.17(16) ?
C6 C5 C11 . . 117.85(16) ?
C4 C5 C11 . . 122.97(16) ?
C7 C6 C5 . . 122.22(16) ?
C7 C6 H6 . . 118.9 ?
C5 C6 H6 . . 118.9 ?
C6 C7 C8 . . 117.69(17) ?
C6 C7 H7 . . 121.2 ?
C8 C7 H7 . . 121.2 ?
C7 C8 C3 . . 121.11(16) ?
C7 C8 N1 . . 129.13(16) ?
C3 C8 N1 . . 109.75(15) ?
O1 C9 N1 . . 121.97(17) ?
O1 C9 C10 . . 121.94(17) ?
N1 C9 C10 . . 116.09(17) ?
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 ?
O2 C11 C5 . . 121.51(17) ?
O2 C11 C12 . . 119.99(16) ?
C5 C11 C12 . . 118.47(15) ?
C11 C12 C13 . . 112.2(5) ?
C11 C12 C13B . . 106.7(7) ?
C13 C12 C13B . . 112.7(8) ?
C11 C12 Cl1B . . 112.0(2) ?
C13 C12 Cl1B . . 2.8(6) ?
C13B C12 Cl1B . . 110.3(6) ?
C11 C12 Cl1 . . 108.14(15) ?
C13 C12 Cl1 . . 109.6(5) ?
C13B C12 Cl1 . . 3.1(7) ?
Cl1B C12 Cl1 . . 107.28(18) ?
C11 C12 H12 . . 109.1 ?
C13 C12 H12 . . 108.7 ?
C13B C12 H12 . . 107.3 ?
Cl1B C12 H12 . . 111.2 ?
Cl1 C12 H12 . . 109.0 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
C12 C13B H13D . . 109.5 ?
C12 C13B H13E . . 109.5 ?
H13D C13B H13E . . 109.5 ?
C12 C13B H13F . . 109.5 ?
H13D C13B H13F . . 109.5 ?
H13E C13B H13F . . 109.5 ?
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
O1 C9 . 1.225(2) ?
O2 C11 . 1.216(2) ?
N1 C9 . 1.362(2) ?
N1 C8 . 1.408(2) ?
N1 C1 . 1.482(2) ?
C1 C2 . 1.525(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.509(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.380(2) ?
C3 C8 . 1.398(2) ?
C4 C5 . 1.402(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(3) ?
C5 C11 . 1.487(2) ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.393(3) ?
C7 H7 . 0.9500 ?
C9 C10 . 1.504(3) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.525(3) ?
C12 C13 . 1.598(10) ?
C12 C13B . 1.641(13) ?
C12 Cl1B . 1.689(3) ?
C12 Cl1 . 1.736(3) ?
C12 H12 . 0.9997 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C13B H13D . 0.9800 ?
C13B H13E . 0.9800 ?
C13B H13F . 0.9800 ?
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
C1 H1B O2 1_545 0.99 2.44 3.252(3) 138.7
C4 H4 O1 1_455 0.95 2.48 3.430(2) 176.5
C12 H12 O1 1_455 1.00 2.41 3.318(2) 151.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . -172.04(17) ?
C8 N1 C1 C2 . . . . 7.0(2) ?
N1 C1 C2 C3 . . . . -7.7(2) ?
C1 C2 C3 C4 . . . . -175.90(19) ?
C1 C2 C3 C8 . . . . 6.2(2) ?
C8 C3 C4 C5 . . . . 1.6(3) ?
C2 C3 C4 C5 . . . . -176.09(18) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
C3 C4 C5 C11 . . . . 177.50(16) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
C11 C5 C6 C7 . . . . -178.82(17) ?
C5 C6 C7 C8 . . . . 0.8(3) ?
C6 C7 C8 C3 . . . . -0.2(3) ?
C6 C7 C8 N1 . . . . 178.75(17) ?
C4 C3 C8 C7 . . . . -1.0(3) ?
C2 C3 C8 C7 . . . . 177.12(17) ?
C4 C3 C8 N1 . . . . 179.83(16) ?
C2 C3 C8 N1 . . . . -2.0(2) ?
C9 N1 C8 C7 . . . . -3.3(3) ?
C1 N1 C8 C7 . . . . 177.69(19) ?
C9 N1 C8 C3 . . . . 175.76(17) ?
C1 N1 C8 C3 . . . . -3.2(2) ?
C8 N1 C9 O1 . . . . 1.8(3) ?
C1 N1 C9 O1 . . . . -179.33(19) ?
C8 N1 C9 C10 . . . . -177.82(17) ?
C1 N1 C9 C10 . . . . 1.1(3) ?
C6 C5 C11 O2 . . . . 12.3(3) ?
C4 C5 C11 O2 . . . . -166.21(17) ?
C6 C5 C11 C12 . . . . -165.37(16) ?
C4 C5 C11 C12 . . . . 16.1(3) ?
O2 C11 C12 C13 . . . . 25.4(6) ?
C5 C11 C12 C13 . . . . -156.9(5) ?
O2 C11 C12 C13B . . . . -98.5(6) ?
C5 C11 C12 C13B . . . . 79.3(6) ?
O2 C11 C12 Cl1B . . . . 22.4(3) ?
C5 C11 C12 Cl1B . . . . -159.9(2) ?
O2 C11 C12 Cl1 . . . . -95.6(2) ?
C5 C11 C12 Cl1 . . . . 82.12(19) ?
C5 C11 C12 Cl1 . . . . 82.12(19) ?
C5 C11 C12 Cl1B . . . . -159.9(2) ?
