#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/19/1511945.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_1511945
loop_
_publ_author_name
'Gogoi, Anupal'
'Guin, Srimanta'
'Rout, Saroj Kumar'
'Patel, Bhisma K.'
_publ_section_title
;
 A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp(3) C-H Bond
 Activation Followed by C-C and C-O Bond Formation.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1802
_journal_page_last               1805
_journal_paper_doi               10.1021/ol400692b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.080(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1536(9)
_cell_length_b                   7.2700(6)
_cell_length_c                   16.7473(14)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.967
_cell_measurement_theta_min      0.948
_cell_volume                     1332.67(19)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'ccd area decetor'
_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  0.1280
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18525
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.0949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                1785
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400692b_si_002.cif
_cod_data_source_block           mp
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P21/n  '
_cod_database_code               1511945
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
C1 C 0.79302(14) 0.98867(19) 0.34359(10) 0.0528(4) Uani 1 1 d .
C2 C 0.67187(14) 0.98869(19) 0.30053(10) 0.0523(4) Uani 1 1 d .
C3 C 0.57230(16) 1.0215(2) 0.33659(12) 0.0632(5) Uani 1 1 d .
H3 H 0.4930 1.0194 0.3065 0.076 Uiso 1 1 calc R
C6 C 0.81303(17) 1.0240(2) 0.42763(10) 0.0649(5) Uani 1 1 d .
H6 H 0.8918 1.0248 0.4586 0.078 Uiso 1 1 calc R
C5 C 0.7144(2) 1.0570(3) 0.46300(12) 0.0760(5) Uani 1 1 d .
H5 H 0.7273 1.0801 0.5186 0.091 Uiso 1 1 calc R
C4 C 0.59543(18) 1.0571(2) 0.41846(13) 0.0727(5) Uani 1 1 d .
H4 H 0.5308 1.0818 0.4446 0.087 Uiso 1 1 calc R
C11 C 1.06794(13) 0.94373(19) 0.23171(9) 0.0501(4) Uani 1 1 d .
C13 C 1.09642(15) 1.0559(2) 0.10170(10) 0.0591(4) Uani 1 1 d .
H13 H 1.0728 1.1357 0.0581 0.071 Uiso 1 1 calc R
C12 C 1.03397(14) 1.0585(2) 0.16426(10) 0.0549(4) Uani 1 1 d .
H12 H 0.9679 1.1378 0.1620 0.066 Uiso 1 1 calc R
C10 C 1.00231(14) 0.9415(2) 0.30074(10) 0.0577(4) Uani 1 1 d .
C9 C 0.87006(13) 0.95727(19) 0.28547(9) 0.0518(4) Uani 1 1 d .
C16 C 1.16845(13) 0.8305(2) 0.23256(11) 0.0601(5) Uani 1 1 d .
H16 H 1.1957 0.7567 0.2778 0.072 Uiso 1 1 calc R
C8 C 0.79227(14) 0.9374(2) 0.21100(10) 0.0538(4) Uani 1 1 d .
H8 H 0.8174 0.9150 0.1621 0.065 Uiso 1 1 calc R
C14 C 1.19397(14) 0.9378(2) 0.10106(10) 0.0583(4) Uani 1 1 d .
C7 C 0.56880(15) 0.9475(2) 0.15357(11) 0.0721(5) Uani 1 1 d .
H7A H 0.5393 1.0699 0.1403 0.108 Uiso 1 1 calc R
H7B H 0.5058 0.8759 0.1705 0.108 Uiso 1 1 calc R
H7C H 0.5911 0.8917 0.1066 0.108 Uiso 1 1 calc R
C15 C 1.22831(14) 0.8247(2) 0.16871(11) 0.0628(5) Uani 1 1 d .
H15 H 1.2933 0.7437 0.1704 0.075 Uiso 1 1 calc R
C17 C 1.25993(17) 0.9330(3) 0.03109(12) 0.0832(6) Uani 1 1 d .
H17A H 1.3016 1.0477 0.0282 0.125 Uiso 1 1 calc R
H17B H 1.2022 0.9138 -0.0186 0.125 Uiso 1 1 calc R
H17C H 1.3183 0.8344 0.0389 0.125 Uiso 1 1 calc R
N1 N 0.67519(11) 0.95495(17) 0.21929(8) 0.0555(4) Uani 1 1 d .
O1 O 1.06084(11) 0.9236(2) 0.37076(8) 0.0892(4) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 117.78(16)
C2 C1 C9 107.12(14)
C6 C1 C9 135.04(15)
C3 C2 N1 129.24(15)
C3 C2 C1 123.37(16)
N1 C2 C1 107.37(15)
C4 C3 C2 117.20(17)
C5 C6 C1 118.67(17)
C6 C5 C4 122.12(19)
C3 C4 C5 120.85(19)
C16 C11 C12 117.09(16)
C16 C11 C10 120.27(14)
C12 C11 C10 122.63(14)
C12 C13 C14 122.08(16)
C13 C12 C11 120.87(15)
O1 C10 C9 120.62(17)
O1 C10 C11 119.45(14)
C9 C10 C11 119.92(14)
C8 C9 C1 105.94(13)
C8 C9 C10 126.18(16)
C1 C9 C10 127.84(14)
C15 C16 C11 121.70(15)
N1 C8 C9 110.49(15)
C13 C14 C15 116.90(17)
C13 C14 C17 121.59(16)
C15 C14 C17 121.50(16)
C16 C15 C14 121.28(15)
C8 N1 C2 109.07(13)
C8 N1 C7 125.77(15)
C2 N1 C7 125.12(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.404(2)
C1 C6 1.406(2)
C1 C9 1.435(2)
C2 C3 1.383(2)
C2 N1 1.390(2)
C3 C4 1.370(2)
C6 C5 1.367(3)
C5 C4 1.392(3)
C11 C16 1.389(2)
C11 C12 1.397(2)
C11 C10 1.483(2)
C13 C12 1.365(2)
C13 C14 1.387(2)
C10 O1 1.2345(18)
C10 C9 1.452(2)
C9 C8 1.383(2)
C16 C15 1.366(2)
C8 N1 1.3455(19)
C14 C15 1.393(2)
C14 C17 1.499(2)
C7 N1 1.4562(19)
