#------------------------------------------------------------------------------
#$Date: 2015-06-07 04:22:07 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138836 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154444.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7154444
loop_
_publ_author_name
'Essa, Ali H.'
'Lerrick, Reinner I.'
'Çiftçi, Eçe'
'Harrington, Ross W.'
'Waddell, Paul G.'
'Clegg, William'
'Hall, Michael J.'
_publ_section_title
;
 Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5793
_journal_page_last               5803
_journal_paper_doi               10.1039/c5ob00541h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C10 H6 Cl3 N O'
_chemical_formula_sum            'C10 H6 Cl3 N O'
_chemical_formula_weight         262.51
_chemical_name_systematic        2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5153(14)
_cell_length_b                   6.7406(4)
_cell_length_c                   7.4148(5)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5101
_cell_measurement_theta_min      2.9152
_cell_volume                     1025.36(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
  1 omega   16.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850   77.0000   60.0000 31

  2 omega   -1.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -120.0000 90

  3 omega  -23.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -180.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0259355000
_diffrn_orient_matrix_UB_12      0.0005132000
_diffrn_orient_matrix_UB_13      -0.0631739000
_diffrn_orient_matrix_UB_21      0.0223930000
_diffrn_orient_matrix_UB_22      0.0076181000
_diffrn_orient_matrix_UB_23      -0.0698909000
_diffrn_orient_matrix_UB_31      0.0045961000
_diffrn_orient_matrix_UB_32      -0.0342371000
_diffrn_orient_matrix_UB_33      -0.0165331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0268P)²+0.4527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1121
_reflns_number_total             1240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh85
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154444
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C10 H7 Cl2 N O'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.19434(2) 0.03543(7) 0.14280(6) 0.02613(15) Uani 1 1 d . . .
Cl2 Cl 0.18075(3) 0.2500 -0.18814(7) 0.02060(16) Uani 1 2 d S T P
O1 O 0.05058(8) 0.2500 -0.0692(2) 0.0209(4) Uani 1 2 d S T P
N1 N 0.04694(10) 0.2500 0.5452(3) 0.0173(4) Uani 1 2 d S T P
C1 C -0.01594(11) 0.2500 0.4771(3) 0.0159(5) Uani 1 2 d S T P
C2 C -0.07483(12) 0.2500 0.5683(3) 0.0199(5) Uani 1 2 d S T P
H2 H -0.0767 0.2500 0.6963 0.024 Uiso 1 2 calc RS T P
C3 C -0.13055(12) 0.2500 0.4647(3) 0.0211(5) Uani 1 2 d S T P
H3 H -0.1719 0.2500 0.5225 0.025 Uiso 1 2 calc RS T P
C4 C -0.12765(11) 0.2500 0.2761(3) 0.0205(5) Uani 1 2 d S T P
H4 H -0.1670 0.2500 0.2086 0.025 Uiso 1 2 calc RS T P
C5 C -0.06857(11) 0.2500 0.1862(3) 0.0179(5) Uani 1 2 d S T P
H5 H -0.0670 0.2500 0.0582 0.022 Uiso 1 2 calc RS T P
C6 C -0.01141(11) 0.2500 0.2882(3) 0.0149(5) Uani 1 2 d S T P
C7 C 0.05778(10) 0.2500 0.2457(3) 0.0156(5) Uani 1 2 d S T P
C8 C 0.08982(11) 0.2500 0.4103(3) 0.0178(5) Uani 1 2 d S T P
H8 H 0.1358 0.2500 0.4248 0.021 Uiso 1 2 calc RS T P
C9 C 0.08372(10) 0.2500 0.0670(3) 0.0148(5) Uani 1 2 d S T P
C10 C 0.15978(11) 0.2500 0.0421(3) 0.0165(5) Uani 1 2 d S T P
H1 H 0.0568(14) 0.2500 0.651(4) 0.029(8) Uiso 1 2 d S T P
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C1 N1 H1 126(2) .
C8 N1 C1 109.97(19) .
C8 N1 H1 124(2) .
N1 C1 C6 107.58(19) .
C2 C1 N1 129.4(2) .
C2 C1 C6 123.0(2) .
C1 C2 H2 121.6 .
C3 C2 C1 116.9(2) .
C3 C2 H2 121.6 .
C2 C3 H3 119.3 .
C2 C3 C4 121.5(2) .
C4 C3 H3 119.3 .
C3 C4 H4 119.4 .
C5 C4 C3 121.3(2) .
C5 C4 H4 119.4 .
C4 C5 H5 120.8 .
C4 C5 C6 118.4(2) .
C6 C5 H5 120.8 .
C1 C6 C7 106.31(19) .
C5 C6 C1 119.0(2) .
C5 C6 C7 134.7(2) .
C8 C7 C6 105.78(19) .
C8 C7 C9 129.8(2) .
C9 C7 C6 124.4(2) .
N1 C8 C7 110.4(2) .
N1 C8 H8 124.8 .
C7 C8 H8 124.8 .
O1 C9 C7 124.2(2) .
O1 C9 C10 117.22(19) .
C7 C9 C10 118.62(19) .
Cl1 C10 Cl1 109.10(12) 8_565
Cl2 C10 Cl1 108.07(9) .
Cl2 C10 Cl1 108.07(9) 8_565
C9 C10 Cl1 110.33(10) 8_565
C9 C10 Cl1 110.32(10) .
C9 C10 Cl2 110.88(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C10 1.7754(13) .
Cl2 C10 1.761(2) .
O1 C9 1.217(3) .
N1 C1 1.385(3) .
N1 C8 1.332(3) .
N1 H1 0.81(3) .
C1 C2 1.384(3) .
C1 C6 1.404(3) .
C2 H2 0.9500 .
C2 C3 1.377(3) .
C3 H3 0.9500 .
C3 C4 1.399(3) .
C4 H4 0.9500 .
C4 C5 1.383(3) .
C5 H5 0.9500 .
C5 C6 1.395(3) .
C6 C7 1.454(3) .
C7 C8 1.386(3) .
C7 C9 1.428(3) .
C8 H8 0.9500 .
C9 C10 1.571(3) .
C10 Cl1 1.7755(13) 8_565
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl2 0.81(3) 2.81(3) 3.383(2) 130(2) 1_556
N1 H1 O1 0.81(3) 2.08(3) 2.861(2) 162(3) 1_556
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_site_symmetry_4
O1 C9 C10 Cl1 -119.69(10) .
O1 C9 C10 Cl1 119.69(10) 8_565
O1 C9 C10 Cl2 0.0 .
N1 C1 C2 C3 180.000(0) .
N1 C1 C6 C5 180.000(0) .
N1 C1 C6 C7 0.000(0) .
C1 N1 C8 C7 0.000(0) .
C1 C2 C3 C4 0.000(0) .
C1 C6 C7 C8 0.000(0) .
C1 C6 C7 C9 180.000(0) .
C2 C1 C6 C5 0.000(0) .
C2 C1 C6 C7 180.000(0) .
C2 C3 C4 C5 0.000(0) .
C3 C4 C5 C6 0.000(0) .
C4 C5 C6 C1 0.000(0) .
C4 C5 C6 C7 180.000(0) .
C5 C6 C7 C8 180.000(0) .
C5 C6 C7 C9 0.000(0) .
C6 C1 C2 C3 0.000(0) .
C6 C7 C8 N1 0.000(0) .
C6 C7 C9 O1 0.000(0) .
C6 C7 C9 C10 180.0 .
C7 C9 C10 Cl1 60.31(10) .
C7 C9 C10 Cl1 -60.31(10) 8_565
C7 C9 C10 Cl2 180.000(0) .
C8 N1 C1 C2 180.000(0) .
C8 N1 C1 C6 0.000(0) .
C8 C7 C9 O1 180.000(0) .
C8 C7 C9 C10 0.000(0) .
C9 C7 C8 N1 180.000(0) .
