#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029650.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_4029650
loop_
_publ_author_name
'Zhang, Yan'
'Zheng, Jing'
'Cui, Sunliang'
_publ_section_title
;
 Rh(III)-Catalyzed C-H Activation/Cyclization of Indoles and Pyrroles:
 Divergent Synthesis of Heterocycles.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6490
_journal_page_last               6500
_journal_paper_doi               10.1021/jo500902n
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 106.912(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.184(3)
_cell_length_b                   10.142(2)
_cell_length_c                   12.177(2)
_cell_measurement_reflns_used    1766
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.36
_cell_volume                     2030.4(6)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL(Sheldrick, 2008)'
_computing_publication_material  'WINGX (Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare,1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       'φ and 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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6085
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0802P)²+1.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                1701
_reflns_number_total             2308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500902n_si_003.cif
_cod_data_source_block           liu_3_0m
_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/ACS/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029650--4029652.cif.
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               4029650
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 N 0.69933(8) 0.10205(14) 0.58318(12) 0.0401(4) Uani 1 1 d .
O1 O 0.59510(8) -0.02246(15) 0.47267(11) 0.0551(4) Uani 1 1 d .
N2 N 0.56844(9) 0.13115(18) 0.59230(14) 0.0541(5) Uani 1 1 d .
H2 H 0.5168 0.1256 0.5608 0.065 Uiso 1 1 calc R
C11 C 0.83524(10) 0.10933(19) 0.61738(14) 0.0428(4) Uani 1 1 d .
C9 C 0.72921(11) 0.21255(17) 0.65274(14) 0.0432(4) Uani 1 1 d .
C5 C 0.76502(10) 0.03812(17) 0.56027(14) 0.0391(4) Uani 1 1 d .
C10 C 0.81063(11) 0.22011(19) 0.67407(14) 0.0464(5) Uani 1 1 d .
C6 C 0.61769(10) 0.06466(19) 0.54467(14) 0.0426(4) Uani 1 1 d .
C4 C 0.76825(12) -0.07525(19) 0.49851(17) 0.0493(5) Uani 1 1 d .
H4 H 0.7212 -0.1205 0.4598 0.059 Uiso 1 1 calc R
C8 C 0.66844(12) 0.2963(2) 0.68545(17) 0.0532(5) Uani 1 1 d .
H8A H 0.6490 0.3646 0.6282 0.064 Uiso 1 1 calc R
H8B H 0.6937 0.3387 0.7586 0.064 Uiso 1 1 calc R
C1 C 0.91082(11) 0.0637(2) 0.61237(17) 0.0566(5) Uani 1 1 d .
H1 H 0.9581 0.1097 0.6488 0.068 Uiso 1 1 calc R
C7 C 0.59771(12) 0.2123(2) 0.69442(17) 0.0561(5) Uani 1 1 d .
H7A H 0.6149 0.1563 0.7618 0.067 Uiso 1 1 calc R
H7B H 0.5541 0.2686 0.7027 0.067 Uiso 1 1 calc R
C3 C 0.84440(13) -0.1188(2) 0.49664(19) 0.0595(6) Uani 1 1 d .
H3 H 0.8485 -0.1956 0.4569 0.071 Uiso 1 1 calc R
C12 C 0.86533(15) 0.3245(2) 0.74176(18) 0.0688(7) Uani 1 1 d .
H12A H 0.9205 0.3063 0.7432 0.103 Uiso 1 1 calc R
H12B H 0.8614 0.3253 0.8188 0.103 Uiso 1 1 calc R
H12C H 0.8493 0.4089 0.7067 0.103 Uiso 1 1 calc R
C2 C 0.91420(13) -0.0507(2) 0.5525(2) 0.0624(6) Uani 1 1 d .
H2A H 0.9644 -0.0823 0.5497 0.075 Uiso 1 1 calc R
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
C6 N1 C5 126.71(15)
C6 N1 C9 124.96(15)
C5 N1 C9 108.33(14)
C6 N2 C7 123.41(16)
C6 N2 H2 118.3
C7 N2 H2 118.3
C1 C11 C5 118.94(18)
C1 C11 C10 133.12(18)
C5 C11 C10 107.92(15)
C10 C9 N1 109.71(16)
C10 C9 C8 133.28(17)
N1 C9 C8 117.00(16)
C4 C5 N1 130.99(16)
C4 C5 C11 122.13(16)
N1 C5 C11 106.85(15)
C9 C10 C11 107.17(16)
C9 C10 C12 126.7(2)
C11 C10 C12 126.15(18)
O1 C6 N2 124.36(16)
O1 C6 N1 120.95(16)
N2 C6 N1 114.69(16)
C5 C4 C3 117.42(18)
C5 C4 H4 121.3
C3 C4 H4 121.3
C9 C8 C7 109.78(16)
C9 C8 H8A 109.7
C7 C8 H8A 109.7
C9 C8 H8B 109.7
C7 C8 H8B 109.7
H8A C8 H8B 108.2
C2 C1 C11 118.94(19)
C2 C1 H1 120.5
C11 C1 H1 120.5
N2 C7 C8 110.02(15)
N2 C7 H7A 109.7
C8 C7 H7A 109.7
N2 C7 H7B 109.7
C8 C7 H7B 109.7
H7A C7 H7B 108.2
C2 C3 C4 121.4(2)
C2 C3 H3 119.3
C4 C3 H3 119.3
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C1 C2 C3 121.14(19)
C1 C2 H2A 119.4
C3 C2 H2A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.396(2)
N1 C5 1.399(2)
N1 C9 1.409(2)
O1 C6 1.226(2)
N2 C6 1.339(2)
N2 C7 1.454(3)
N2 H2 0.8600
C11 C1 1.397(3)
C11 C5 1.405(2)
C11 C10 1.445(3)
C9 C10 1.349(3)
C9 C8 1.488(3)
C5 C4 1.384(3)
C10 C12 1.494(3)
C4 C3 1.388(3)
C4 H4 0.9300
C8 C7 1.514(3)
C8 H8A 0.9700
C8 H8B 0.9700
C1 C2 1.380(3)
C1 H1 0.9300
C7 H7A 0.9700
C7 H7B 0.9700
C3 C2 1.380(3)
C3 H3 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C2 H2A 0.9300
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
N2 H2 O1 0.86 2.12 2.906(2) 151.4 5_656
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
C6 N1 C9 C10 -179.98(15)
C5 N1 C9 C10 0.01(19)
C6 N1 C9 C8 -1.1(2)
C5 N1 C9 C8 178.87(14)
C6 N1 C5 C4 -1.4(3)
C9 N1 C5 C4 178.62(18)
C6 N1 C5 C11 -179.32(15)
C9 N1 C5 C11 0.69(18)
C1 C11 C5 C4 -0.5(3)
C10 C11 C5 C4 -179.25(16)
C1 C11 C5 N1 177.67(15)
C10 C11 C5 N1 -1.10(18)
N1 C9 C10 C11 -0.69(19)
C8 C9 C10 C11 -179.30(18)
N1 C9 C10 C12 178.31(17)
C8 C9 C10 C12 -0.3(3)
C1 C11 C10 C9 -177.41(19)
C5 C11 C10 C9 1.12(19)
C1 C11 C10 C12 3.6(3)
C5 C11 C10 C12 -177.89(17)
C7 N2 C6 O1 165.86(19)
C7 N2 C6 N1 -14.3(3)
C5 N1 C6 O1 -9.4(3)
C9 N1 C6 O1 170.53(16)
C5 N1 C6 N2 170.67(15)
C9 N1 C6 N2 -9.3(2)
N1 C5 C4 C3 -176.31(17)
C11 C5 C4 C3 1.3(3)
C10 C9 C8 C7 -150.4(2)
N1 C9 C8 C7 31.1(2)
C5 C11 C1 C2 -0.7(3)
C10 C11 C1 C2 177.72(19)
C6 N2 C7 C8 44.6(3)
C9 C8 C7 N2 -49.6(2)
C5 C4 C3 C2 -1.1(3)
C11 C1 C2 C3 0.9(3)
C4 C3 C2 C1 0.0(3)
