#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/09/7120936.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_7120936
loop_
_publ_author_name
'Zhou, Peng'
'Wang, Jia-Yin'
'Zhang, Tian-Shu'
'Li, Guigen'
'Hao, Wen-Juan'
'Tu, Shu-Jiang'
'Jiang, Bo'
_publ_section_title
;
 Thiazolium salt-catalyzed C-C triple bond cleavage for accessing
 substituted 1-naphthols via benzannulation.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              164
_journal_page_last               167
_journal_paper_doi               10.1039/c7cc08792f
_journal_volume                  54
_journal_year                    2017
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_update_record
;
2017-06-07 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.868(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3531(7)
_cell_length_b                   10.7592(9)
_cell_length_c                   14.2252(13)
_cell_measurement_reflns_used    945
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.813
_cell_measurement_theta_min      2.899
_cell_volume                     1414.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1055
_diffrn_reflns_av_sigmaI/netI    0.1544
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6514
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1916
_refine_ls_R_factor_gt           0.0774
_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)+(0.0584P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1814
_reflns_number_gt                958
_reflns_number_total             2460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc08792f2.cif
_cod_data_source_block           160418a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7120935--7120936.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7120936
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
Cl1 Cl 1.42929(17) 0.13498(17) 1.05148(13) 0.0803(7) Uani 1 1 d .
N1 N 0.7182(5) 0.2233(5) 0.8021(3) 0.0513(13) Uani 1 1 d .
O1 O 0.6942(4) 0.1448(4) 0.4692(2) 0.0580(12) Uani 1 1 d .
H1 H 0.7281 0.1680 0.4224 0.087 Uiso 1 1 calc R
O2 O 0.8992(5) 0.4917(4) 0.8271(3) 0.0720(14) Uani 1 1 d .
C1 C 0.6182(7) 0.1387(7) 0.8029(5) 0.068(2) Uani 1 1 d .
H1A H 0.5845 0.1252 0.8602 0.081 Uiso 1 1 calc R
C2 C 0.5579(7) 0.0672(6) 0.7258(5) 0.069(2) Uani 1 1 d .
H2 H 0.4878 0.0077 0.7319 0.083 Uiso 1 1 calc R
C3 C 0.6038(6) 0.0865(6) 0.6412(4) 0.0584(18) Uani 1 1 d .
H3 H 0.5657 0.0399 0.5882 0.070 Uiso 1 1 calc R
C4 C 0.7086(6) 0.1767(5) 0.6342(4) 0.0397(15) Uani 1 1 d .
C5 C 0.7690(6) 0.2447(5) 0.7167(4) 0.0415(15) Uani 1 1 d .
C6 C 0.8832(6) 0.3277(5) 0.7139(4) 0.0446(16) Uani 1 1 d .
C7 C 0.9328(6) 0.3509(5) 0.6293(4) 0.0496(16) Uani 1 1 d .
C8 C 0.8676(7) 0.2890(6) 0.5463(4) 0.0509(16) Uani 1 1 d .
H8 H 0.8986 0.3075 0.4888 0.061 Uiso 1 1 calc R
C9 C 0.7621(7) 0.2042(6) 0.5474(4) 0.0492(16) Uani 1 1 d .
C10 C 0.9454(7) 0.3910(6) 0.8032(4) 0.0487(16) Uani 1 1 d .
C11 C 1.0729(6) 0.3326(5) 0.8620(4) 0.0425(15) Uani 1 1 d .
C12 C 1.1304(6) 0.2245(5) 0.8332(4) 0.0519(16) Uani 1 1 d .
H12 H 1.0932 0.1917 0.7740 0.062 Uiso 1 1 calc R
C13 C 1.2426(7) 0.1622(6) 0.8896(5) 0.0589(18) Uani 1 1 d .
H13 H 1.2805 0.0889 0.8691 0.071 Uiso 1 1 calc R
C14 C 1.2962(6) 0.2132(6) 0.9777(5) 0.0503(16) Uani 1 1 d .
C15 C 1.2431(6) 0.3236(6) 1.0081(4) 0.0559(17) Uani 1 1 d .
H15 H 1.2810 0.3571 1.0669 0.067 Uiso 1 1 calc R
C16 C 1.1333(6) 0.3830(6) 0.9498(4) 0.0505(16) Uani 1 1 d .
H16 H 1.0984 0.4582 0.9691 0.061 Uiso 1 1 calc R
C17 C 1.0612(6) 0.4363(6) 0.6261(4) 0.0625(19) Uani 1 1 d .
H17A H 1.0557 0.5056 0.6678 0.094 Uiso 1 1 calc R
H17B H 1.0599 0.4658 0.5623 0.094 Uiso 1 1 calc R
H17C H 1.1493 0.3913 0.6462 0.094 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C5 117.7(5)
C9 O1 H1 109.5
N1 C1 C2 125.8(6)
N1 C1 H1A 117.1
C2 C1 H1A 117.1
C3 C2 C1 118.1(6)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C3 C4 119.6(6)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 119.5(5)
C3 C4 C9 123.3(6)
C5 C4 C9 117.3(5)
N1 C5 C6 119.8(5)
N1 C5 C4 119.3(5)
C6 C5 C4 120.8(5)
C7 C6 C5 120.2(5)
C7 C6 C10 121.7(5)
C5 C6 C10 118.0(5)
C6 C7 C8 119.0(5)
C6 C7 C17 120.7(5)
C8 C7 C17 120.2(5)
C9 C8 C7 122.3(6)
C9 C8 H8 118.9
C7 C8 H8 118.9
C8 C9 O1 124.3(5)
C8 C9 C4 120.2(6)
O1 C9 C4 115.4(5)
O2 C10 C6 122.2(6)
O2 C10 C11 120.1(6)
C6 C10 C11 117.6(5)
C12 C11 C16 118.2(6)
C12 C11 C10 120.6(5)
C16 C11 C10 121.1(5)
C11 C12 C13 122.2(6)
C11 C12 H12 118.9
C13 C12 H12 118.9
C14 C13 C12 117.7(6)
C14 C13 H13 121.1
C12 C13 H13 121.1
C15 C14 C13 121.6(6)
C15 C14 Cl1 119.4(5)
C13 C14 Cl1 118.9(5)
C16 C15 C14 118.8(6)
C16 C15 H15 120.6
C14 C15 H15 120.6
C15 C16 C11 121.3(6)
C15 C16 H16 119.3
C11 C16 H16 119.3
C7 C17 H17A 109.5
C7 C17 H17B 109.5
H17A C17 H17B 109.5
C7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.719(6)
N1 C1 1.306(7)
N1 C5 1.389(6)
O1 C9 1.353(6)
O1 H1 0.8200
O2 C10 1.233(6)
C1 C2 1.386(8)
C1 H1A 0.9300
C2 C3 1.354(7)
C2 H2 0.9300
C3 C4 1.393(7)
C3 H3 0.9300
C4 C5 1.425(7)
C4 C9 1.433(7)
C5 C6 1.397(7)
C6 C7 1.378(7)
C6 C10 1.480(8)
C7 C8 1.409(7)
C7 C17 1.518(7)
C8 C9 1.347(7)
C8 H8 0.9300
C10 C11 1.486(8)
C11 C12 1.369(7)
C11 C16 1.398(7)
C12 C13 1.391(7)
C12 H12 0.9300
C13 C14 1.389(8)
C13 H13 0.9300
C14 C15 1.382(7)
C15 C16 1.375(7)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C5 N1 C1 C2 0.3(10)
N1 C1 C2 C3 -0.9(11)
C1 C2 C3 C4 -0.2(9)
C2 C3 C4 C5 1.8(9)
C2 C3 C4 C9 -179.3(6)
C1 N1 C5 C6 -175.3(5)
C1 N1 C5 C4 1.4(8)
C3 C4 C5 N1 -2.5(8)
C9 C4 C5 N1 178.5(5)
C3 C4 C5 C6 174.2(5)
C9 C4 C5 C6 -4.7(8)
N1 C5 C6 C7 -179.0(5)
C4 C5 C6 C7 4.3(8)
N1 C5 C6 C10 -0.5(8)
C4 C5 C6 C10 -177.2(5)
C5 C6 C7 C8 -0.6(8)
C10 C6 C7 C8 -179.0(5)
C5 C6 C7 C17 -177.2(5)
C10 C6 C7 C17 4.3(8)
C6 C7 C8 C9 -2.6(9)
C17 C7 C8 C9 174.0(5)
C7 C8 C9 O1 178.4(5)
C7 C8 C9 C4 2.1(9)
C3 C4 C9 C8 -177.3(5)
C5 C4 C9 C8 1.6(8)
C3 C4 C9 O1 6.0(8)
C5 C4 C9 O1 -175.0(5)
C7 C6 C10 O2 88.4(7)
C5 C6 C10 O2 -90.1(7)
C7 C6 C10 C11 -88.1(7)
C5 C6 C10 C11 93.4(6)
O2 C10 C11 C12 -176.1(5)
C6 C10 C11 C12 0.5(8)
O2 C10 C11 C16 6.8(8)
C6 C10 C11 C16 -176.6(5)
C16 C11 C12 C13 2.1(8)
C10 C11 C12 C13 -175.1(5)
C11 C12 C13 C14 0.0(9)
C12 C13 C14 C15 -1.5(9)
C12 C13 C14 Cl1 177.1(4)
C13 C14 C15 C16 0.8(9)
Cl1 C14 C15 C16 -177.8(4)
C14 C15 C16 C11 1.4(8)
C12 C11 C16 C15 -2.8(8)
C10 C11 C16 C15 174.3(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188220
