#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/46/7114625.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_7114625
loop_
_publ_author_name
'Xue Zhang'
'Yifei Li'
'Hui Shi'
'Lunan Zhang'
'Shanshan Zhang'
'Xianxiu Xu'
'Qun Liu'
_publ_section_title
;
 Rhodium(III)-catalyzed intramolecular amidoarylation and hydroarylation
 of alkyne via C-H activation: switchable synthesis of 3,4-fused tricyclic
 indoles and chromans
;
_journal_name_full               Chem.Commun.
_journal_page_first              7306
_journal_paper_doi               10.1039/C4CC02398F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           161
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   25.053(2)
_cell_length_b                   25.053(2)
_cell_length_c                   9.6450(13)
_cell_measurement_temperature    293(2)
_cell_volume                     5242.7(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9786
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0552
_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)+(0.0782P)²+5.0595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1481
_reflns_number_total             2054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02398f2.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'MIXED' changed to 'mixed'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

2018-02-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C39 H45 N3 O6'
_cod_original_formula_weight         651.78
_cod_original_formula_units_Z            6
_cod_original_sg_symbol_H-M      R3C
_cod_database_code               7114625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'-y+2/3, -x+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
'-y+1/3, -x+2/3, z+7/6'
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
C3 C 0.19815(18) -0.02295(17) 0.2453(3) 0.0392(9) Uani 1 1 d .
N1 N 0.13849(15) -0.06943(15) 0.2064(3) 0.0391(8) Uani 1 1 d .
C8 C 0.22763(17) 0.03387(17) 0.1742(4) 0.0381(9) Uani 1 1 d .
C9 C 0.19758(19) 0.05399(18) 0.0701(4) 0.0447(10) Uani 1 1 d .
C2 C 0.09395(19) -0.10841(18) 0.2944(4) 0.0431(10) Uani 1 1 d .
O1 O 0.09969(15) -0.10320(16) 0.4201(3) 0.0632(9) Uani 1 1 d .
O2 O 0.32360(15) 0.12854(16) 0.1359(4) 0.0732(11) Uani 1 1 d .
C12 C 0.1382(2) 0.03757(18) 0.0678(5) 0.0501(11) Uani 1 1 d .
H12 H 0.1135 0.0098 0.1357 0.060 Uiso 1 1 calc R
C4 C 0.2297(2) -0.0352(2) 0.3466(4) 0.0516(11) Uani 1 1 d .
H4 H 0.2100 -0.0727 0.3935 0.062 Uiso 1 1 calc R
C1 C 0.0367(2) -0.1585(2) 0.2271(5) 0.0567(12) Uani 1 1 d .
H1A H 0.0413 -0.1550 0.1281 0.085 Uiso 1 1 calc R
H1B H 0.0019 -0.1547 0.2542 0.085 Uiso 1 1 calc R
H1C H 0.0304 -0.1980 0.2558 0.085 Uiso 1 1 calc R
C6 C 0.3208(2) 0.0616(2) 0.3062(4) 0.0556(12) Uani 1 1 d .
H6 H 0.3620 0.0894 0.3252 0.067 Uiso 1 1 calc R
C7 C 0.2900(2) 0.0747(2) 0.2039(4) 0.0490(10) Uani 1 1 d .
C10 C 0.2423(2) 0.1012(3) -0.0305(6) 0.089(2) Uani 1 1 d .
H10A H 0.2453 0.0799 -0.1115 0.107 Uiso 1 1 calc R
H10B H 0.2258 0.1270 -0.0607 0.107 Uiso 1 1 calc R
C13 C 0.1070(2) 0.0585(2) -0.0306(6) 0.0758(15) Uani 1 1 d .
H13A H 0.0640 0.0393 -0.0076 0.114 Uiso 1 1 calc R
H13B H 0.1114 0.0472 -0.1233 0.114 Uiso 1 1 calc R
H13C H 0.1253 0.1024 -0.0248 0.114 Uiso 1 1 calc R
C5 C 0.2901(2) 0.0074(2) 0.3790(5) 0.0610(13) Uani 1 1 d .
H5 H 0.3100 -0.0006 0.4504 0.073 Uiso 1 1 calc R
C11 C 0.2989(4) 0.1374(4) 0.0201(9) 0.139(3) Uani 1 1 d U
H11A H 0.3029 0.1777 0.0309 0.167 Uiso 1 1 calc R
H11B H 0.3268 0.1415 -0.0542 0.167 Uiso 1 1 calc R
H1N H 0.1318(19) -0.0678(19) 0.130(5) 0.039(12) Uiso 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
C4 C3 N1 119.4(4)
C4 C3 C8 119.9(4)
N1 C3 C8 120.5(3)
C2 N1 C3 125.4(3)
C2 N1 H1N 122(3)
C3 N1 H1N 113(3)
C7 C8 C3 117.8(4)
C7 C8 C9 117.3(4)
C3 C8 C9 124.9(3)
C12 C9 C8 125.7(4)
C12 C9 C10 120.7(4)
C8 C9 C10 113.4(4)
O1 C2 N1 122.4(4)
O1 C2 C1 122.1(4)
N1 C2 C1 115.5(4)
C11 O2 C7 117.3(4)
C9 C12 C13 127.4(4)
C9 C12 H12 116.3
C13 C12 H12 116.3
C5 C4 C3 120.9(4)
C5 C4 H4 119.6
C3 C4 H4 119.6
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C5 C6 C7 119.6(4)
C5 C6 H6 120.2
C7 C6 H6 120.2
O2 C7 C6 116.0(4)
O2 C7 C8 122.7(4)
C6 C7 C8 121.4(4)
C11 C10 C9 114.7(5)
C11 C10 H10A 108.6
C9 C10 H10A 108.6
C11 C10 H10B 108.6
C9 C10 H10B 108.6
H10A C10 H10B 107.6
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
C6 C5 C4 120.3(4)
C6 C5 H5 119.8
C4 C5 H5 119.8
C10 C11 O2 127.6(6)
C10 C11 H11A 105.4
O2 C11 H11A 105.4
C10 C11 H11B 105.4
O2 C11 H11B 105.4
H11A C11 H11B 106.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C4 1.384(5)
C3 N1 1.411(5)
C3 C8 1.411(5)
N1 C2 1.353(5)
N1 H1N 0.76(5)
C8 C7 1.404(6)
C8 C9 1.486(6)
C9 C12 1.330(5)
C9 C10 1.507(6)
C2 O1 1.220(4)
C2 C1 1.501(6)
O2 C11 1.347(7)
O2 C7 1.350(6)
C12 C13 1.483(6)
C12 H12 0.9300
C4 C5 1.383(7)
C4 H4 0.9300
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C6 C5 1.372(7)
C6 C7 1.390(6)
C6 H6 0.9300
C10 C11 1.337(9)
C10 H10A 0.9700
C10 H10B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C5 H5 0.9300
C11 H11A 0.9700
C11 H11B 0.9700
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
C4 C3 N1 C2 41.5(6)
C8 C3 N1 C2 -143.7(4)
C4 C3 C8 C7 3.9(5)
N1 C3 C8 C7 -170.9(3)
C4 C3 C8 C9 -175.9(4)
N1 C3 C8 C9 9.3(5)
C7 C8 C9 C12 -150.2(4)
C3 C8 C9 C12 29.7(6)
C7 C8 C9 C10 24.4(5)
C3 C8 C9 C10 -155.7(4)
C3 N1 C2 O1 6.8(6)
C3 N1 C2 C1 -173.4(4)
C8 C9 C12 C13 177.4(4)
C10 C9 C12 C13 3.2(7)
N1 C3 C4 C5 174.5(4)
C8 C3 C4 C5 -0.3(6)
C11 O2 C7 C6 167.9(6)
C11 O2 C7 C8 -12.1(8)
C5 C6 C7 O2 -179.3(4)
C5 C6 C7 C8 0.7(6)
C3 C8 C7 O2 175.9(4)
C9 C8 C7 O2 -4.3(6)
C3 C8 C7 C6 -4.1(5)
C9 C8 C7 C6 175.7(4)
C12 C9 C10 C11 145.8(7)
C8 C9 C10 C11 -29.1(8)
C7 C6 C5 C4 3.0(6)
C3 C4 C5 C6 -3.2(6)
C9 C10 C11 O2 15.1(14)
C7 O2 C11 C10 6.3(13)
