#------------------------------------------------------------------------------
#$Date: 2019-11-25 20:44:12 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/15/4131592.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_4131592
loop_
_publ_author_name
'Tan, Guangying'
'Zhu, Lei'
'Liao, Xingrong'
'Lan, Yu'
'You, Jingsong'
_publ_section_title
;
 Rhodium/Copper Cocatalyzed Highly trans-Selective 1,2-Diheteroarylation
 of Alkynes with Azoles via C-H Addition/Oxidative Cross-Coupling: A
 Combined Experimental and Theoretical Study.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15724
_journal_page_last               15737
_journal_paper_doi               10.1021/jacs.7b07242
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C14 H9 N O'
_chemical_formula_sum            'C14 H9 N O'
_chemical_formula_weight         207.22
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.934(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9409(13)
_cell_length_b                   5.0852(4)
_cell_length_c                   23.2360(18)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.2950
_cell_measurement_theta_min      4.9170
_cell_volume                     2118.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   89.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740 -125.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   89.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740 -125.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00   63.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00  103.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740   77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   90.00  175.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   98.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   90.00  175.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  175.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega  100.00  178.00   1.0000   17.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 15 omega    9.00  103.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 16 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega  -31.00   53.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
 18 omega   19.00  103.00   1.0000    4.4700
omega____ theta____ kappa____ phi______ frames
    -       35.8740   57.0000  -60.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0783649000
_diffrn_orient_matrix_UB_12      0.0505272000
_diffrn_orient_matrix_UB_13      0.0227672000
_diffrn_orient_matrix_UB_21      0.0117761000
_diffrn_orient_matrix_UB_22      -0.2225004000
_diffrn_orient_matrix_UB_23      0.0443614000
_diffrn_orient_matrix_UB_31      0.0331459000
_diffrn_orient_matrix_UB_32      0.1992747000
_diffrn_orient_matrix_UB_33      0.0437817000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.370
_diffrn_reflns_theta_min         4.933
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0872
_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)+(0.1650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.3121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1136
_reflns_number_total             2062
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b07242_si_002.cif
_cod_data_source_block           tgy-0629
_cod_database_code               4131592
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-29
_olex2_submission_special_instructions 'No special instructions were received'
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
O001 O 0.52389(16) 0.5912(6) 0.35041(13) 0.0874(10) Uani 1 1 d .
N002 N 0.60901(17) 0.2748(8) 0.34828(13) 0.0812(11) Uani 1 1 d .
C003 C 0.59946(17) 0.3384(8) 0.22000(15) 0.0647(10) Uani 1 1 d .
C004 C 0.53626(17) 0.3716(7) 0.25912(16) 0.0630(9) Uani 1 1 d .
C005 C 0.55701(18) 0.4023(8) 0.31995(16) 0.0646(10) Uani 1 1 d .
C006 C 0.66110(19) 0.5030(9) 0.22511(17) 0.0739(11) Uani 1 1 d .
H006 H 0.6623 0.6336 0.2531 0.089 Uiso 1 1 calc R
C007 C 0.6120(2) 0.3871(9) 0.40256(16) 0.0768(12) Uani 1 1 d .
C008 C 0.5590(2) 0.5817(9) 0.40356(17) 0.0800(12) Uani 1 1 d .
C009 C 0.5998(2) 0.1413(9) 0.17934(17) 0.0788(12) Uani 1 1 d .
H009 H 0.5592 0.0280 0.1754 0.095 Uiso 1 1 calc R
C00A C 0.6599(3) 0.1111(10) 0.1444(2) 0.0927(14) Uani 1 1 d .
H00A H 0.6600 -0.0241 0.1175 0.111 Uiso 1 1 calc R
C00B C 0.7205(2) 0.4765(11) 0.1895(2) 0.0858(13) Uani 1 1 d .
H00B H 0.7607 0.5914 0.1930 0.103 Uiso 1 1 calc R
C00C C 0.7201(3) 0.2816(12) 0.1493(2) 0.0937(15) Uani 1 1 d .
H00C H 0.7601 0.2630 0.1251 0.112 Uiso 1 1 calc R
C00D C 0.6565(3) 0.3356(14) 0.4506(2) 0.114(2) Uani 1 1 d .
H00D H 0.6923 0.2035 0.4504 0.137 Uiso 1 1 calc R
C00E C 0.6464(4) 0.4839(16) 0.4985(2) 0.120(2) Uani 1 1 d .
H00E H 0.6761 0.4545 0.5315 0.144 Uiso 1 1 calc R
C00F C 0.5484(4) 0.7330(15) 0.4508(2) 0.138(3) Uani 1 1 d .
H00F H 0.5130 0.8669 0.4507 0.165 Uiso 1 1 calc R
C00G C 0.5926(5) 0.6775(16) 0.4985(2) 0.142(3) Uani 1 1 d .
H00G H 0.5861 0.7736 0.5321 0.170 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
C005 O001 C008 104.6(3) .
C005 N002 C007 105.1(4) .
C006 C003 C004 120.1(4) .
C009 C003 C004 121.5(3) .
C009 C003 C006 118.4(4) .
C004 C004 C003 123.6(4) 2_655
C004 C004 C005 121.0(4) 2_655
C005 C004 C003 115.5(3) .
O001 C005 C004 119.0(3) .
N002 C005 O001 114.4(3) .
N002 C005 C004 126.5(4) .
C003 C006 H006 119.3 .
C00B C006 C003 121.3(4) .
C00B C006 H006 119.3 .
C008 C007 N002 107.9(3) .
C008 C007 C00D 120.5(4) .
C00D C007 N002 131.7(5) .
O001 C008 C007 107.9(3) .
C00F C008 O001 129.5(5) .
C00F C008 C007 122.5(5) .
C003 C009 H009 119.8 .
C003 C009 C00A 120.4(4) .
C00A C009 H009 119.8 .
C009 C00A H00A 119.8 .
C009 C00A C00C 120.3(5) .
C00C C00A H00A 119.8 .
C006 C00B H00B 120.1 .
C00C C00B C006 119.8(4) .
C00C C00B H00B 120.1 .
C00A C00C H00C 120.1 .
C00B C00C C00A 119.7(4) .
C00B C00C H00C 120.1 .
C007 C00D H00D 121.0 .
C00E C00D C007 117.9(5) .
C00E C00D H00D 121.0 .
C00D C00E H00E 119.7 .
C00D C00E C00G 120.6(5) .
C00G C00E H00E 119.7 .
C008 C00F H00F 121.8 .
C008 C00F C00G 116.4(6) .
C00G C00F H00F 121.8 .
C00E C00G H00G 118.9 .
C00F C00G C00E 122.2(6) .
C00F C00G H00G 118.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O001 C005 1.343(5) .
O001 C008 1.368(5) .
N002 C005 1.297(4) .
N002 C007 1.384(5) .
C003 C004 1.486(5) .
C003 C006 1.389(5) .
C003 C009 1.378(5) .
C004 C004 1.355(6) 2_655
C004 C005 1.458(5) .
C006 H006 0.9300 .
C006 C00B 1.377(6) .
C007 C008 1.374(6) .
C007 C00D 1.376(5) .
C008 C00F 1.359(7) .
C009 H009 0.9300 .
C009 C00A 1.380(6) .
C00A H00A 0.9300 .
C00A C00C 1.387(7) .
C00B H00B 0.9300 .
C00B C00C 1.363(7) .
C00C H00C 0.9300 .
C00D H00D 0.9300 .
C00D C00E 1.361(8) .
C00E H00E 0.9300 .
C00E C00G 1.379(9) .
C00F H00F 0.9300 .
C00F C00G 1.372(8) .
C00G H00G 0.9300 .
