#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029651.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_4029651
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_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.042(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0763(5)
_cell_length_b                   12.2352(5)
_cell_length_c                   12.0706(7)
_cell_measurement_reflns_used    1931
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.4149
_cell_measurement_theta_min      3.3185
_cell_volume                     1281.59(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5123
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0395
_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)+(0.0387P)²+0.3632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                1886
_reflns_number_total             2340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500902n_si_002.cif
_cod_data_source_block           131101_zy_6_28_1
_cod_depositor_comments
'Adding full bibliography for 4029650--4029652.cif.'
_cod_original_cell_volume        1281.58(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029651
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.82774(11) 0.06687(9) 0.46999(9) 0.0310(3) Uani 1 1 d .
N1 N 0.70220(13) 0.05787(9) 0.60797(10) 0.0228(3) Uani 1 1 d .
N2 N 0.94043(14) -0.02219(10) 0.63900(10) 0.0259(3) Uani 1 1 d .
H2 H 1.0216 -0.0364 0.6156 0.031 Uiso 1 1 calc R
C1 C 0.57195(15) 0.12111(11) 0.55531(12) 0.0232(3) Uani 1 1 d .
C2 C 0.52985(17) 0.17556(12) 0.45007(13) 0.0282(3) Uani 1 1 d .
H2A H 0.5915 0.1726 0.3987 0.034 Uiso 1 1 calc R
C3 C 0.39408(18) 0.23440(13) 0.42327(13) 0.0335(4) Uani 1 1 d .
H3 H 0.3626 0.2738 0.3524 0.040 Uiso 1 1 calc R
C4 C 0.30228(18) 0.23731(14) 0.49750(14) 0.0363(4) Uani 1 1 d .
H4 H 0.2087 0.2776 0.4758 0.044 Uiso 1 1 calc R
C5 C 0.34465(18) 0.18287(13) 0.60180(13) 0.0339(4) Uani 1 1 d .
H5 H 0.2810 0.1853 0.6517 0.041 Uiso 1 1 calc R
C6 C 0.48279(16) 0.12395(12) 0.63334(12) 0.0267(3) Uani 1 1 d .
C7 C 0.56191(17) 0.06203(13) 0.73383(13) 0.0297(4) Uani 1 1 d .
H7 H 0.5279 0.0503 0.8002 0.036 Uiso 1 1 calc R
C8 C 0.69424(16) 0.02303(12) 0.71766(12) 0.0251(3) Uani 1 1 d .
C9 C 0.82430(16) 0.03545(11) 0.56573(12) 0.0242(3) Uani 1 1 d .
C10 C 0.94230(16) -0.06092(11) 0.74843(12) 0.0249(3) Uani 1 1 d .
C11 C 0.82089(16) -0.03957(12) 0.78661(12) 0.0267(3) Uani 1 1 d .
H11 H 0.8190 -0.0662 0.8601 0.032 Uiso 1 1 calc R
C12 C 1.08663(17) -0.12393(12) 0.81223(13) 0.0288(4) Uani 1 1 d .
C13 C 1.1034(2) -0.22435(13) 0.74081(14) 0.0394(4) Uani 1 1 d .
H13A H 1.0183 -0.2751 0.7362 0.059 Uiso 1 1 calc R
H13B H 1.2016 -0.2608 0.7781 0.059 Uiso 1 1 calc R
H13C H 1.1011 -0.2013 0.6626 0.059 Uiso 1 1 calc R
C14 C 1.07828(19) -0.16189(15) 0.93092(13) 0.0383(4) Uani 1 1 d .
H14A H 1.0658 -0.0983 0.9767 0.057 Uiso 1 1 calc R
H14B H 1.1735 -0.2005 0.9712 0.057 Uiso 1 1 calc R
H14C H 0.9902 -0.2112 0.9209 0.057 Uiso 1 1 calc R
C15 C 1.22814(18) -0.04961(15) 0.82946(16) 0.0434(4) Uani 1 1 d .
H15A H 1.2374 -0.0276 0.7537 0.065 Uiso 1 1 calc R
H15B H 1.3211 -0.0894 0.8724 0.065 Uiso 1 1 calc R
H15C H 1.2161 0.0155 0.8733 0.065 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
C9 N1 C1 127.33(12)
C9 N1 C8 123.70(12)
C1 N1 C8 108.90(11)
C9 N2 C10 125.68(12)
C9 N2 H2 117.2
C10 N2 H2 117.2
C2 C1 N1 130.65(13)
C2 C1 C6 122.84(13)
N1 C1 C6 106.49(12)
C3 C2 C1 116.93(14)
C3 C2 H2A 121.5
C1 C2 H2A 121.5
C2 C3 C4 121.60(14)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 121.16(14)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 119.10(14)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C1 118.35(13)
C5 C6 C7 133.64(14)
C1 C6 C7 108.01(12)
C8 C7 C6 108.01(13)
C8 C7 H7 126.0
C6 C7 H7 126.0
C7 C8 N1 108.59(13)
C7 C8 C11 134.35(14)
N1 C8 C11 117.03(12)
O1 C9 N2 123.16(13)
O1 C9 N1 122.14(13)
N2 C9 N1 114.69(12)
C11 C10 N2 118.40(13)
C11 C10 C12 126.75(13)
N2 C10 C12 114.85(12)
C10 C11 C8 120.47(13)
C10 C11 H11 119.8
C8 C11 H11 119.8
C10 C12 C14 110.90(12)
C10 C12 C13 109.53(12)
C14 C12 C13 108.88(13)
C10 C12 C15 109.28(12)
C14 C12 C15 108.77(13)
C13 C12 C15 109.46(13)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.2270(17)
N1 C9 1.3764(18)
N1 C1 1.3999(17)
N1 C8 1.4128(18)
N2 C9 1.3580(18)
N2 C10 1.3987(18)
N2 H2 0.8800
C1 C2 1.385(2)
C1 C6 1.411(2)
C2 C3 1.381(2)
C2 H2A 0.9500
C3 C4 1.391(2)
C3 H3 0.9500
C4 C5 1.376(2)
C4 H4 0.9500
C5 C6 1.399(2)
C5 H5 0.9500
C6 C7 1.432(2)
C7 C8 1.359(2)
C7 H7 0.9500
C8 C11 1.428(2)
C10 C11 1.339(2)
C10 C12 1.521(2)
C11 H11 0.9500
C12 C14 1.529(2)
C12 C13 1.534(2)
C12 C15 1.537(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
