#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555954.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_1555954
loop_
_publ_author_name
'Cheng, Wanli'
'Tang, Yanhua'
'Xu, Ze-Feng'
'Li, Chuan-Ying'
_publ_section_title
;
 Synthesis of Multifunctionalized 2-Carbonylpyrrole by Rhodium-Catalyzed
 Transannulation of 1-Sulfonyl-1,2,3-triazole with β-Diketone.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6168
_journal_page_last               6171
_journal_paper_doi               10.1021/acs.orglett.6b03179
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.023(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4161(15)
_cell_length_b                   5.5776(5)
_cell_length_c                   15.6055(14)
_cell_measurement_reflns_used    5416
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1122.39(19)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8074
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.075(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0500
_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)+(0.0663P)²+0.3024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                1278
_reflns_number_total             1952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03179_si_002.cif
_cod_data_source_block           zbb-1
_cod_database_code               1555954
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.60353(19) 0.3114(4) 0.44376(16) 0.0693(7) Uani 1 1 d .
C2 C 0.54066(17) 0.2273(4) 0.35892(15) 0.0622(6) Uani 1 1 d .
C3 C 0.52500(18) 0.3019(4) 0.27068(15) 0.0650(6) Uani 1 1 d .
C4 C 0.44576(19) 0.1566(4) 0.21967(16) 0.0710(7) Uani 1 1 d .
H4 H 0.4187 0.1656 0.1581 0.085 Uiso 1 1 calc R
C5 C 0.41391(18) -0.0017(4) 0.27424(15) 0.0652(6) Uani 1 1 d .
C6 C 0.5758(2) 0.5048(5) 0.23523(17) 0.0834(8) Uani 1 1 d .
H6A H 0.5885 0.6350 0.2771 0.125 Uiso 1 1 calc R
H6B H 0.5309 0.5580 0.1793 0.125 Uiso 1 1 calc R
H6C H 0.6403 0.4509 0.2267 0.125 Uiso 1 1 calc R
C7 C 0.3348(2) -0.1964(5) 0.25531(18) 0.0820(8) Uani 1 1 d .
H7A H 0.3680 -0.3473 0.2522 0.123 Uiso 1 1 calc R
H7B H 0.2844 -0.1653 0.1995 0.123 Uiso 1 1 calc R
H7C H 0.3010 -0.2020 0.3021 0.123 Uiso 1 1 calc R
C8 C 0.69442(18) 0.4700(4) 0.44922(15) 0.0652(6) Uani 1 1 d .
C9 C 0.7069(2) 0.6736(5) 0.50125(16) 0.0786(8) Uani 1 1 d .
H9 H 0.6569 0.7152 0.5297 0.094 Uiso 1 1 calc R
C10 C 0.7936(3) 0.8158(6) 0.51115(19) 0.1001(10) Uani 1 1 d .
H10 H 0.8014 0.9556 0.5448 0.120 Uiso 1 1 calc R
C11 C 0.8686(3) 0.7487(7) 0.4707(2) 0.1079(12) Uani 1 1 d .
H11 H 0.9278 0.8421 0.4784 0.129 Uiso 1 1 calc R
C12 C 0.8569(2) 0.5471(7) 0.4196(2) 0.1035(10) Uani 1 1 d .
H12 H 0.9079 0.5036 0.3925 0.124 Uiso 1 1 calc R
C13 C 0.7696(2) 0.4082(5) 0.40811(18) 0.0826(8) Uani 1 1 d .
H13 H 0.7612 0.2719 0.3725 0.099 Uiso 1 1 calc R
N1 N 0.47099(14) 0.0444(3) 0.35803(12) 0.0657(6) Uani 1 1 d .
H1 H 0.4649 -0.0298 0.4046 0.079 Uiso 1 1 calc R
O1 O 0.58525(15) 0.2506(4) 0.51416(11) 0.0944(7) 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
O1 C1 C2 121.2(2)
O1 C1 C8 118.1(2)
C2 C1 C8 120.6(2)
N1 C2 C3 107.0(2)
N1 C2 C1 118.3(2)
C3 C2 C1 134.5(2)
C4 C3 C2 105.8(2)
C4 C3 C6 125.3(2)
C2 C3 C6 128.8(2)
C5 C4 C3 109.7(2)
C5 C4 H4 125.1
C3 C4 H4 125.1
N1 C5 C4 106.8(2)
N1 C5 C7 121.0(2)
C4 C5 C7 132.2(2)
C3 C6 H6A 109.5
C3 C6 H6B 109.5
H6A C6 H6B 109.5
C3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 119.6(2)
C9 C8 C1 119.2(2)
C13 C8 C1 121.1(2)
C8 C9 C10 120.0(3)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 119.4(3)
C11 C10 H10 120.3
C9 C10 H10 120.3
C12 C11 C10 120.8(3)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C13 119.9(3)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C8 120.3(3)
C12 C13 H13 119.9
C8 C13 H13 119.9
C5 N1 C2 110.67(19)
C5 N1 H1 124.7
C2 N1 H1 124.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.237(3)
C1 C2 1.438(3)
C1 C8 1.490(3)
C2 N1 1.381(3)
C2 C3 1.398(3)
C3 C4 1.398(3)
C3 C6 1.503(3)
C4 C5 1.374(3)
C4 H4 0.9300
C5 N1 1.345(3)
C5 C7 1.490(3)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.379(3)
C8 C13 1.381(3)
C9 C10 1.381(4)
C9 H9 0.9300
C10 C11 1.378(5)
C10 H10 0.9300
C11 C12 1.363(5)
C11 H11 0.9300
C12 C13 1.373(4)
C12 H12 0.9300
C13 H13 0.9300
N1 H1 0.8600
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
N1 H1 O1 0.86 2.01 2.843(2) 163 3_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
O1 C1 C2 N1 -11.3(4)
C8 C1 C2 N1 167.2(2)
O1 C1 C2 C3 162.0(3)
C8 C1 C2 C3 -19.5(4)
N1 C2 C3 C4 -0.5(3)
C1 C2 C3 C4 -174.3(3)
N1 C2 C3 C6 176.0(2)
C1 C2 C3 C6 2.1(4)
C2 C3 C4 C5 -0.1(3)
C6 C3 C4 C5 -176.7(2)
C3 C4 C5 N1 0.7(3)
C3 C4 C5 C7 -178.7(2)
O1 C1 C8 C9 -49.0(3)
C2 C1 C8 C9 132.5(2)
O1 C1 C8 C13 126.6(3)
C2 C1 C8 C13 -51.9(3)
C13 C8 C9 C10 0.7(4)
C1 C8 C9 C10 176.4(2)
C8 C9 C10 C11 -1.8(4)
C9 C10 C11 C12 1.5(5)
C10 C11 C12 C13 -0.1(5)
C11 C12 C13 C8 -1.0(4)
C9 C8 C13 C12 0.7(4)
C1 C8 C13 C12 -174.9(2)
C4 C5 N1 C2 -1.0(3)
C7 C5 N1 C2 178.4(2)
C3 C2 N1 C5 0.9(3)
C1 C2 N1 C5 175.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14611992
