#------------------------------------------------------------------------------
#$Date: 2016-05-06 03:18:51 +0200 (vie 06 de may de 2016) $
#$Revision: 182690 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/85/7038594.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_7038594
loop_
_publ_author_name
'Singh, Mahabir P.'
'Saleem, Fariha'
'Rao, Gyandshwar K.'
'Kumar, S.'
'Joshi, Hemant'
'Singh, Ajai K.'
_publ_section_title
;
 Palladacycles of unsymmetrical (N,C(-),E) (E = S/Se) pincers based on
 indole: their synthesis, structure and application in the catalysis of
 Heck coupling and allylation of aldehydes.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6718
_journal_page_last               6725
_journal_paper_doi               10.1039/c6dt00060f
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C11 H10 Cl N O'
_chemical_formula_sum            'C11 H10 Cl N O'
_chemical_formula_weight         207.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc14q8ty
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-09 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.558(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.037(2)
_cell_length_b                   9.870(3)
_cell_length_c                   11.840(3)
_cell_measurement_reflns_used    2705
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.990
_cell_measurement_theta_min      2.45
_cell_volume                     982.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0240
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9105
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             432.0
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0535
_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)+(0.0357P)²+0.7824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                1588
_reflns_number_total             1726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt00060f2.cif
_cod_data_source_block           pd844m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7038593--7038596.cif.
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7038594
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.69966(9) 0.54384(8) 1.09545(8) 0.0596(3) Uani 1 1 d .
N1 N 0.8405(2) 0.8218(2) 1.03696(18) 0.0363(5) Uani 1 1 d .
C4 C 1.0349(3) 0.8077(2) 0.9620(2) 0.0341(5) Uani 1 1 d .
C9 C 0.6440(3) 0.9596(3) 0.8702(2) 0.0434(6) Uani 1 1 d .
H9 H 0.5647 0.9601 0.9027 0.052 Uiso 1 1 calc R
C6 C 0.8823(3) 0.9538(2) 0.7689(2) 0.0400(6) Uani 1 1 d .
H6 H 0.9594 0.9517 0.7342 0.048 Uiso 1 1 calc R
C5 C 0.9062(3) 0.8853(2) 0.8776(2) 0.0328(5) Uani 1 1 d .
C11 C 1.1888(3) 0.7761(3) 0.9594(2) 0.0435(6) Uani 1 1 d .
H11 H 1.2569 0.7255 1.0238 0.052 Uiso 1 1 calc R
C3 C 0.9883(3) 0.7729(2) 1.0564(2) 0.0365(6) Uani 1 1 d .
H3 H 1.0494 0.7229 1.1241 0.044 Uiso 1 1 calc R
O1 O 1.2383(2) 0.8091(2) 0.88111(19) 0.0598(6) Uani 1 1 d .
C8 C 0.6251(3) 1.0268(3) 0.7637(3) 0.0476(7) Uani 1 1 d .
H8 H 0.5317 1.0748 0.7242 0.057 Uiso 1 1 calc R
C10 C 0.7865(3) 0.8913(2) 0.9269(2) 0.0336(5) Uani 1 1 d .
C7 C 0.7429(3) 1.0243(3) 0.7140(2) 0.0464(7) Uani 1 1 d .
H7 H 0.7270 1.0712 0.6424 0.056 Uiso 1 1 calc R
C2 C 0.7583(3) 0.8140(3) 1.1222(2) 0.0465(7) Uani 1 1 d .
H2A H 0.7156 0.9027 1.1284 0.056 Uiso 1 1 calc R
H2B H 0.8347 0.7904 1.2018 0.056 Uiso 1 1 calc R
C1 C 0.6253(3) 0.7126(3) 1.0866(3) 0.0497(7) Uani 1 1 d .
H1A H 0.5530 0.7308 1.0044 0.060 Uiso 1 1 calc R
H1B H 0.5663 0.7215 1.1401 0.060 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0584(5) 0.0488(5) 0.0743(6) -0.0018(4) 0.0275(4) -0.0048(3)
N1 0.0365(11) 0.0376(12) 0.0373(11) 0.0016(9) 0.0164(9) -0.0016(9)
C4 0.0363(13) 0.0281(12) 0.0360(13) -0.0035(10) 0.0111(11) 0.0005(10)
C9 0.0381(14) 0.0420(15) 0.0513(16) -0.0022(13) 0.0179(12) 0.0007(12)
C6 0.0507(15) 0.0357(14) 0.0373(14) -0.0051(11) 0.0207(12) -0.0031(12)
C5 0.0367(13) 0.0245(12) 0.0364(13) -0.0059(10) 0.0126(11) -0.0031(10)
C11 0.0421(14) 0.0391(15) 0.0474(15) -0.0045(12) 0.0142(13) 0.0039(12)
C3 0.0377(13) 0.0298(12) 0.0381(13) 0.0014(10) 0.0094(11) 0.0011(10)
O1 0.0552(12) 0.0765(15) 0.0600(13) 0.0036(11) 0.0355(11) 0.0111(11)
C8 0.0429(15) 0.0430(16) 0.0484(16) 0.0022(13) 0.0068(13) 0.0065(12)
C10 0.0356(13) 0.0302(12) 0.0345(13) -0.0025(10) 0.0123(10) -0.0026(10)
C7 0.0594(17) 0.0407(15) 0.0326(14) 0.0017(11) 0.0090(13) 0.0000(13)
C2 0.0548(16) 0.0463(16) 0.0449(15) 0.0014(13) 0.0261(13) 0.0013(13)
C1 0.0427(15) 0.0580(18) 0.0557(17) 0.0117(14) 0.0267(13) 0.0042(13)
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
C3 N1 C10 108.59(19)
C3 N1 C2 125.7(2)
C10 N1 C2 125.5(2)
C3 C4 C11 123.5(2)
C3 C4 C5 106.6(2)
C11 C4 C5 129.8(2)
C8 C9 C10 117.2(2)
C7 C6 C5 118.9(2)
C6 C5 C10 118.6(2)
C6 C5 C4 135.0(2)
C10 C5 C4 106.4(2)
O1 C11 C4 126.2(3)
N1 C3 C4 110.4(2)
C9 C8 C7 121.4(2)
C9 C10 N1 129.5(2)
C9 C10 C5 122.5(2)
N1 C10 C5 108.0(2)
C6 C7 C8 121.3(2)
N1 C2 C1 113.6(2)
C2 C1 Cl1 111.15(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.784(3)
N1 C3 1.358(3)
N1 C10 1.392(3)
N1 C2 1.459(3)
C4 C3 1.374(3)
C4 C11 1.437(3)
C4 C5 1.443(3)
C9 C8 1.378(4)
C9 C10 1.389(3)
C6 C7 1.375(4)
C6 C5 1.399(3)
C5 C10 1.407(3)
C11 O1 1.212(3)
C8 C7 1.393(4)
C2 C1 1.501(4)
