#------------------------------------------------------------------------------
#$Date: 2019-11-04 17:44:08 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/44/4514418.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_4514418
loop_
_publ_author_name
'Zhao, Kang'
'Du, Rongrong'
'Wang, Bingyang'
'Liu, Jianhua'
'Xia, Chungu'
'Yang, Lei'
_publ_section_title
;
 RhCl3·3H2O-Catalyzed Regioselective C(sp2)--H Alkoxycarbonylation:
 Efficient Synthesis of Indole- and Pyrrole-2-carboxylic Acid Esters
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5545
_journal_paper_doi               10.1021/acscatal.9b01193
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C15 H11 N3 O2'
_chemical_formula_weight         265.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.533(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.260(4)
_cell_length_b                   6.4425(14)
_cell_length_c                   20.274(5)
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.68
_cell_volume                     2473.3(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8272
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.363
_diffrn_reflns_theta_min         2.043
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.6686
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1621
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2440
_reflns_number_total             3603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b01193_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4514415--4514418.cif.
;
_cod_original_cell_volume        2473.3(9)
_cod_database_code               4514418
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.00630(7) 0.9040(2) 0.12588(6) 0.0372(3) Uani 1 1 d . .
C2 C -0.05368(7) 0.8254(3) 0.14677(7) 0.0491(4) Uani 1 1 d . .
H2 H -0.0519 0.7055 0.1726 0.059 Uiso 1 1 calc R U
C3 C -0.11581(8) 0.9344(3) 0.12728(8) 0.0582(5) Uani 1 1 d . .
H3 H -0.1567 0.8849 0.1400 0.070 Uiso 1 1 calc R U
C4 C -0.11960(8) 1.1147(3) 0.08946(8) 0.0580(5) Uani 1 1 d . .
H4 H -0.1628 1.1816 0.0767 0.070 Uiso 1 1 calc R U
C5 C -0.06032(8) 1.1952(3) 0.07071(7) 0.0510(4) Uani 1 1 d . .
H5 H -0.0627 1.3176 0.0461 0.061 Uiso 1 1 calc R U
C6 C 0.00402(7) 1.0898(2) 0.08925(6) 0.0387(3) Uani 1 1 d . .
C7 C 0.07424(7) 1.1297(2) 0.07846(6) 0.0371(3) Uani 1 1 d . .
C8 C 0.11564(7) 0.9724(2) 0.10690(6) 0.0339(3) Uani 1 1 d . .
C9 C 0.18385(7) 0.9275(2) 0.08805(6) 0.0365(3) Uani 1 1 d . .
C10 C 0.18354(9) 1.2951(2) 0.06509(8) 0.0511(4) Uani 1 1 d . .
H10A H 0.2050 1.3889 0.0372 0.061 Uiso 1 1 calc R U
H10B H 0.1943 1.3461 0.1108 0.061 Uiso 1 1 calc R U
C11 C 0.10446(8) 1.2953(2) 0.04156(7) 0.0462(4) Uani 1 1 d . .
H11A H 0.0850 1.4290 0.0505 0.055 Uiso 1 1 calc R U
H11B H 0.0932 1.2693 -0.0063 0.055 Uiso 1 1 calc R U
C12 C 0.10426(6) 0.6786(2) 0.18399(6) 0.0342(3) Uani 1 1 d . .
C13 C 0.19644(8) 0.5684(3) 0.26002(7) 0.0538(4) Uani 1 1 d . .
H13 H 0.2423 0.5849 0.2836 0.065 Uiso 1 1 calc R U
C14 C 0.16049(9) 0.3925(3) 0.27027(8) 0.0542(4) Uani 1 1 d . .
H14 H 0.1804 0.2908 0.3004 0.065 Uiso 1 1 calc R U
C15 C 0.09364(9) 0.3733(3) 0.23394(8) 0.0514(4) Uani 1 1 d . .
H15 H 0.0674 0.2565 0.2406 0.062 Uiso 1 1 calc R U
N1 N 0.07594(5) 0.82904(17) 0.13644(5) 0.0359(3) Uani 1 1 d . .
N2 N 0.16884(6) 0.71747(19) 0.21785(6) 0.0443(3) Uani 1 1 d . .
N3 N 0.06443(6) 0.51478(18) 0.18934(6) 0.0439(3) Uani 1 1 d . .
O1 O 0.21109(5) 0.75951(16) 0.08924(6) 0.0508(3) Uani 1 1 d . .
O2 O 0.21410(5) 1.08973(16) 0.06242(5) 0.0480(3) 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 N1 130.48(13)
C2 C1 C6 121.43(12)
N1 C1 C6 108.07(11)
C3 C2 C1 116.77(15)
C3 C2 H2 121.6
C1 C2 H2 121.6
C2 C3 C4 122.65(15)
C2 C3 H3 118.7
C4 C3 H3 118.7
C5 C4 C3 120.55(14)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 118.89(15)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 119.64(13)
C5 C6 C7 133.24(14)
C1 C6 C7 107.11(11)
C8 C7 C6 107.48(11)
C8 C7 C11 119.98(12)
C6 C7 C11 132.47(12)
C7 C8 N1 110.54(11)
C7 C8 C9 121.66(11)
N1 C8 C9 124.59(11)
O1 C9 O2 119.29(12)
O1 C9 C8 125.65(12)
O2 C9 C8 114.83(11)
O2 C10 C11 112.40(12)
O2 C10 H10A 109.1
C11 C10 H10A 109.1
O2 C10 H10B 109.1
C11 C10 H10B 109.1
H10A C10 H10B 107.9
C7 C11 C10 107.84(11)
C7 C11 H11A 110.1
C10 C11 H11A 110.1
C7 C11 H11B 110.1
C10 C11 H11B 110.1
H11A C11 H11B 108.5
N3 C12 N2 127.62(12)
N3 C12 N1 116.69(11)
N2 C12 N1 115.69(11)
N2 C13 C14 122.92(15)
N2 C13 H13 118.5
C14 C13 H13 118.5
C13 C14 C15 116.59(14)
C13 C14 H14 121.7
C15 C14 H14 121.7
N3 C15 C14 122.84(14)
N3 C15 H15 118.6
C14 C15 H15 118.6
C8 N1 C1 106.78(10)
C8 N1 C12 125.04(11)
C1 N1 C12 125.59(11)
C12 N2 C13 114.96(13)
C12 N3 C15 114.99(12)
C9 O2 C10 119.06(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3961(19)
C1 N1 1.4046(16)
C1 C6 1.405(2)
C2 C3 1.381(2)
C2 H2 0.9300
C3 C4 1.386(3)
C3 H3 0.9300
C4 C5 1.369(2)
C4 H4 0.9300
C5 C6 1.4025(19)
C5 H5 0.9300
C6 C7 1.4321(18)
C7 C8 1.3518(18)
C7 C11 1.4819(19)
C8 N1 1.4013(16)
C8 C9 1.4627(17)
C9 O1 1.2009(16)
C9 O2 1.3463(16)
C10 O2 1.4529(18)
C10 C11 1.511(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 N3 1.3208(17)
C12 N2 1.3301(17)
C12 N1 1.4050(16)
C13 N2 1.3303(19)
C13 C14 1.364(2)
C13 H13 0.9300
C14 C15 1.367(2)
C14 H14 0.9300
C15 N3 1.3339(18)
C15 H15 0.9300
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
N1 C1 C2 C3 -179.05(14)
C6 C1 C2 C3 2.6(2)
C1 C2 C3 C4 -0.7(2)
C2 C3 C4 C5 -1.3(3)
C3 C4 C5 C6 1.3(2)
C4 C5 C6 C1 0.6(2)
C4 C5 C6 C7 -179.79(14)
C2 C1 C6 C5 -2.6(2)
N1 C1 C6 C5 178.70(12)
C2 C1 C6 C7 177.66(12)
N1 C1 C6 C7 -0.99(14)
C5 C6 C7 C8 -178.93(15)
C1 C6 C7 C8 0.70(15)
C5 C6 C7 C11 -2.2(3)
C1 C6 C7 C11 177.41(13)
C6 C7 C8 N1 -0.15(15)
C11 C7 C8 N1 -177.34(11)
C6 C7 C8 C9 160.48(12)
C11 C7 C8 C9 -16.72(19)
C7 C8 C9 O1 -150.13(14)
N1 C8 C9 O1 7.7(2)
C7 C8 C9 O2 24.31(18)
N1 C8 C9 O2 -177.86(11)
C8 C7 C11 C10 -20.86(17)
C6 C7 C11 C10 162.77(14)
O2 C10 C11 C7 50.96(15)
N2 C13 C14 C15 0.9(2)
C13 C14 C15 N3 1.5(2)
C7 C8 N1 C1 -0.47(14)
C9 C8 N1 C1 -160.40(12)
C7 C8 N1 C12 -162.98(12)
C9 C8 N1 C12 37.08(19)
C2 C1 N1 C8 -177.59(14)
C6 C1 N1 C8 0.90(14)
C2 C1 N1 C12 -15.2(2)
C6 C1 N1 C12 163.29(12)
N3 C12 N1 C8 -157.19(12)
N2 C12 N1 C8 21.99(18)
N3 C12 N1 C1 43.53(18)
N2 C12 N1 C1 -137.30(13)
N3 C12 N2 C13 2.6(2)
N1 C12 N2 C13 -176.50(12)
C14 C13 N2 C12 -2.7(2)
N2 C12 N3 C15 -0.4(2)
N1 C12 N3 C15 178.64(12)
C14 C15 N3 C12 -1.7(2)
O1 C9 O2 C10 -176.00(13)
C8 C9 O2 C10 9.18(17)
C11 C10 O2 C9 -47.60(17)
