#------------------------------------------------------------------------------
#$Date: 2015-06-07 04:22:07 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138836 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154445.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_7154445
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         'C11 H8 Cl3 N O'
_chemical_formula_sum            'C11 H8 Cl3 N O'
_chemical_formula_weight         276.53
_chemical_name_systematic
'2,2,2-trichloro-1-(1-methyl-1H-indol-3-yl)ethan-1-one '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_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                 98.358(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8736(5)
_cell_length_b                   11.2992(4)
_cell_length_c                   10.6096(5)
_cell_measurement_reflns_used    3708
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5575
_cell_measurement_theta_min      3.1856
_cell_volume                     1171.08(9)
_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      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details
;
  1 omega  -63.00    3.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  -38.0000  -60.0000 66

  2 omega  -63.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  -38.0000    0.0000 82

  3 omega  -32.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  112.0000   11.0000 26

  4 omega  -48.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600    0.0000   30.0000 147
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0065681000
_diffrn_orient_matrix_UB_12      -0.0294857000
_diffrn_orient_matrix_UB_13      -0.0596028000
_diffrn_orient_matrix_UB_21      0.0604548000
_diffrn_orient_matrix_UB_22      0.0281131000
_diffrn_orient_matrix_UB_23      -0.0136151000
_diffrn_orient_matrix_UB_31      0.0396741000
_diffrn_orient_matrix_UB_32      -0.0477329000
_diffrn_orient_matrix_UB_33      0.0288213000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_laue_measured_fraction_full 0.988
_diffrn_reflns_laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9535
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.594
_diffrn_reflns_theta_min         3.192
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92180
_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    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0303
_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)+(0.0277P)²+0.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2165
_reflns_number_total             2573
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh88
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154445
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C11 H8 Cl3 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.
;
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.752
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl1 Cl 0.07438(5) 0.16419(4) 0.15589(4) 0.02801(12) Uani 1 1 d .
Cl2 Cl -0.00613(5) 0.35121(4) 0.31666(5) 0.03011(13) Uani 1 1 d .
Cl3 Cl -0.02966(5) 0.10937(4) 0.38923(5) 0.03406(13) Uani 1 1 d .
O1 O 0.25315(13) 0.13279(10) 0.46510(11) 0.0293(3) Uani 1 1 d .
N1 N 0.41174(15) 0.44632(12) 0.25823(13) 0.0227(3) Uani 1 1 d .
C1 C 0.07056(17) 0.20977(14) 0.31627(16) 0.0213(4) Uani 1 1 d .
C2 C 0.22147(17) 0.21036(14) 0.38699(15) 0.0194(3) Uani 1 1 d .
C3 C 0.31446(17) 0.29921(14) 0.35502(15) 0.0191(3) Uani 1 1 d .
C4 C 0.29744(18) 0.38215(14) 0.25733(15) 0.0202(3) Uani 1 1 d .
H4 H 0.2162 0.3920 0.1982 0.024 Uiso 1 1 calc R
C5 C 0.45227(17) 0.31605(14) 0.42082(16) 0.0210(4) Uani 1 1 d .
C6 C 0.53117(18) 0.26375(16) 0.52663(16) 0.0272(4) Uani 1 1 d .
H6 H 0.4956 0.2011 0.5717 0.033 Uiso 1 1 calc R
C7 C 0.6625(2) 0.30604(19) 0.56363(19) 0.0366(5) Uani 1 1 d .
H7 H 0.7178 0.2709 0.6345 0.044 Uiso 1 1 calc R
C8 C 0.7157(2) 0.39881(19) 0.4996(2) 0.0389(5) Uani 1 1 d .
H8 H 0.8062 0.4257 0.5282 0.047 Uiso 1 1 calc R
C9 C 0.64040(19) 0.45235(18) 0.39616(19) 0.0328(4) Uani 1 1 d .
H9 H 0.6764 0.5158 0.3526 0.039 Uiso 1 1 calc R
C10 C 0.50861(17) 0.40908(15) 0.35815(16) 0.0233(4) Uani 1 1 d .
C11 C 0.4315(2) 0.54210(16) 0.17046(17) 0.0310(4) Uani 1 1 d .
H11A H 0.3512 0.5477 0.1046 0.047 Uiso 1 1 calc GR
H11B H 0.5130 0.5260 0.1304 0.047 Uiso 1 1 calc GR
H11C H 0.4436 0.6169 0.2174 0.047 Uiso 1 1 calc GR
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
C4 N1 C10 109.15(14)
C4 N1 C11 125.96(15)
C10 N1 C11 124.88(15)
Cl2 C1 Cl1 109.37(9)
Cl3 C1 Cl1 108.98(9)
Cl3 C1 Cl2 108.28(9)
C2 C1 Cl1 107.90(11)
C2 C1 Cl2 111.87(11)
C2 C1 Cl3 110.41(11)
O1 C2 C1 117.11(14)
O1 C2 C3 123.77(15)
C3 C2 C1 119.10(13)
C2 C3 C5 124.52(15)
C4 C3 C2 129.53(15)
C4 C3 C5 105.92(14)
N1 C4 C3 110.44(15)
N1 C4 H4 124.8
C3 C4 H4 124.8
C6 C5 C3 134.81(17)
C6 C5 C10 118.93(16)
C10 C5 C3 106.24(14)
C5 C6 H6 121.0
C7 C6 C5 118.07(18)
C7 C6 H6 121.0
C6 C7 H7 119.1
C6 C7 C8 121.74(18)
C8 C7 H7 119.1
C7 C8 H8 119.3
C9 C8 C7 121.47(18)
C9 C8 H8 119.3
C8 C9 H9 121.6
C8 C9 C10 116.81(19)
C10 C9 H9 121.6
N1 C10 C5 108.25(14)
N1 C10 C9 128.78(17)
C9 C10 C5 122.97(17)
N1 C11 H11A 109.5
N1 C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7834(17)
Cl2 C1 1.7687(17)
Cl3 C1 1.7573(17)
O1 C2 1.2155(19)
N1 C4 1.340(2)
N1 C10 1.386(2)
N1 C11 1.459(2)
C1 C2 1.568(2)
C2 C3 1.434(2)
C3 C4 1.389(2)
C3 C5 1.449(2)
C4 H4 0.9500
C5 C6 1.401(2)
C5 C10 1.402(2)
C6 H6 0.9500
C6 C7 1.384(3)
C7 H7 0.9500
C7 C8 1.393(3)
C8 H8 0.9500
C8 C9 1.374(3)
C9 H9 0.9500
C9 C10 1.394(2)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
Cl1 C1 C2 O1 -108.10(15)
Cl1 C1 C2 C3 70.60(16)
Cl2 C1 C2 O1 131.56(14)
Cl2 C1 C2 C3 -49.73(18)
Cl3 C1 C2 O1 10.91(18)
Cl3 C1 C2 C3 -170.39(12)
O1 C2 C3 C4 170.56(17)
O1 C2 C3 C5 -7.2(3)
C1 C2 C3 C4 -8.0(3)
C1 C2 C3 C5 174.20(14)
C2 C3 C4 N1 -177.82(16)
C2 C3 C5 C6 -3.0(3)
C2 C3 C5 C10 178.55(15)
C3 C5 C6 C7 -178.97(18)
C3 C5 C10 N1 -0.82(18)
C3 C5 C10 C9 178.84(15)
C4 N1 C10 C5 1.00(18)
C4 N1 C10 C9 -178.63(17)
C4 C3 C5 C6 178.82(18)
C4 C3 C5 C10 0.35(18)
C5 C3 C4 N1 0.26(18)
C5 C6 C7 C8 0.8(3)
C6 C5 C10 N1 -179.58(14)
C6 C5 C10 C9 0.1(3)
C6 C7 C8 C9 -0.3(3)
C7 C8 C9 C10 -0.3(3)
C8 C9 C10 N1 179.96(17)
C8 C9 C10 C5 0.4(3)
C10 N1 C4 C3 -0.78(19)
C10 C5 C6 C7 -0.6(2)
C11 N1 C4 C3 -179.52(15)
C11 N1 C10 C5 179.76(15)
C11 N1 C10 C9 0.1(3)
