#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/27/7122752.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_7122752
loop_
_publ_author_name
'Luo, Mu-Jia'
'Hu, Ming'
'Song, Ren-Jie'
'He, De-Liang'
'Li, Jin-Heng'
_publ_section_title
;
 Ruthenium(II)-Catalyzed Electrooxidative [4+2] Annulation of Benzylic
 Alcohols with Internal Alkynes: Entry to Isocoumarins
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08759H
_journal_year                    2018
_chemical_formula_moiety         C18H14O2
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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-97
_audit_update_record
;
2018-10-20 deposited with the CCDC.
2018-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 125.704(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.242(4)
_cell_length_b                   10.3242(19)
_cell_length_c                   14.505(3)
_cell_measurement_reflns_used    3945
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.26
_cell_volume                     2704.7(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10142
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0419
_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)+(0.0565P)²+0.6414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                1932
_reflns_number_total             2517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc08759h2.cif
_cod_data_source_block           a
_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 
;
_cod_original_cell_volume        2704.8(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7122752
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.28297(9) 0.55620(16) 0.32090(15) 0.0721(4) Uani 1 1 d .
H1 H 0.2598 0.6008 0.2525 0.087 Uiso 1 1 calc R
C2 C 0.35972(10) 0.55343(18) 0.39464(19) 0.0870(6) Uani 1 1 d .
H2 H 0.3878 0.5951 0.3749 0.104 Uiso 1 1 calc R
C3 C 0.39425(11) 0.4897(2) 0.4963(2) 0.0956(7) Uani 1 1 d .
H3 H 0.4457 0.4888 0.5456 0.115 Uiso 1 1 calc R
C4 C 0.35329(11) 0.42724(18) 0.52552(16) 0.0885(6) Uani 1 1 d .
H4 H 0.3769 0.3851 0.5951 0.106 Uiso 1 1 calc R
C5 C 0.27738(10) 0.42678(15) 0.45223(13) 0.0723(4) Uani 1 1 d .
H5 H 0.2500 0.3820 0.4717 0.087 Uiso 1 1 calc R
C6 C 0.24085(8) 0.49264(14) 0.34909(12) 0.0615(4) Uani 1 1 d .
C7 C 0.15932(8) 0.49129(14) 0.27241(11) 0.0558(4) Uani 1 1 d .
C8 C 0.11155(8) 0.58928(13) 0.21711(11) 0.0516(3) Uani 1 1 d .
C9 C 0.03279(8) 0.56121(13) 0.14507(11) 0.0515(3) Uani 1 1 d .
C10 C 0.00820(8) 0.43416(13) 0.13671(11) 0.0557(4) Uani 1 1 d .
C11 C 0.06145(9) 0.33035(14) 0.19723(13) 0.0618(4) Uani 1 1 d .
C12 C 0.13598(8) 0.72652(13) 0.22680(12) 0.0577(4) Uani 1 1 d .
H12 H 0.1355 0.7576 0.1625 0.069 Uiso 1 1 calc R
C13 C 0.11529(10) 0.82601(16) 0.27892(15) 0.0761(5) Uani 1 1 d .
H13A H 0.1012 0.9114 0.2446 0.091 Uiso 1 1 calc R
H13B H 0.0892 0.7967 0.3102 0.091 Uiso 1 1 calc R
C14 C 0.19335(11) 0.78663(17) 0.33775(15) 0.0849(5) Uani 1 1 d .
H14A H 0.2151 0.7335 0.4053 0.102 Uiso 1 1 calc R
H14B H 0.2270 0.8481 0.3396 0.102 Uiso 1 1 calc R
C15 C -0.06715(9) 0.40458(16) 0.06986(12) 0.0665(4) Uani 1 1 d .
H15 H -0.0825 0.3196 0.0653 0.080 Uiso 1 1 calc R
C16 C -0.11844(9) 0.49995(18) 0.01119(14) 0.0718(4) Uani 1 1 d .
H16 H -0.1687 0.4804 -0.0324 0.086 Uiso 1 1 calc R
C17 C -0.09531(9) 0.62555(17) 0.01683(14) 0.0695(4) Uani 1 1 d .
H17 H -0.1303 0.6903 -0.0240 0.083 Uiso 1 1 calc R
C18 C -0.02131(8) 0.65636(15) 0.08200(12) 0.0609(4) Uani 1 1 d .
H18 H -0.0069 0.7416 0.0843 0.073 Uiso 1 1 calc R
O1 O 0.13475(6) 0.36468(9) 0.26379(9) 0.0647(3) Uani 1 1 d .
O2 O 0.04780(7) 0.21721(10) 0.19477(11) 0.0854(4) 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'
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
C6 C1 C2 120.11(17)
C6 C1 H1 119.9
C2 C1 H1 119.9
C3 C2 C1 120.3(2)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 120.20(19)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 120.09(19)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 120.83(18)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 118.46(15)
C1 C6 C7 121.84(14)
C5 C6 C7 119.69(14)
C8 C7 O1 121.41(13)
C8 C7 C6 129.81(13)
O1 C7 C6 108.78(12)
C7 C8 C9 118.78(12)
C7 C8 C12 122.75(13)
C9 C8 C12 118.47(12)
C10 C9 C18 117.21(14)
C10 C9 C8 119.73(13)
C18 C9 C8 123.06(13)
C15 C10 C9 121.05(14)
C15 C10 C11 118.94(13)
C9 C10 C11 120.00(14)
O2 C11 O1 116.62(15)
O2 C11 C10 126.62(15)
O1 C11 C10 116.76(12)
C14 C12 C8 122.22(13)
C14 C12 C13 59.30(11)
C8 C12 C13 119.70(13)
C14 C12 H12 114.8
C8 C12 H12 114.8
C13 C12 H12 114.8
C14 C13 C12 59.92(11)
C14 C13 H13A 117.8
C12 C13 H13A 117.8
C14 C13 H13B 117.8
C12 C13 H13B 117.8
H13A C13 H13B 114.9
C13 C14 C12 60.78(11)
C13 C14 H14A 117.7
C12 C14 H14A 117.7
C13 C14 H14B 117.7
C12 C14 H14B 117.7
H14A C14 H14B 114.8
C16 C15 C10 120.24(15)
C16 C15 H15 119.9
C10 C15 H15 119.9
C15 C16 C17 119.61(15)
C15 C16 H16 120.2
C17 C16 H16 120.2
C18 C17 C16 120.92(16)
C18 C17 H17 119.5
C16 C17 H17 119.5
C17 C18 C9 120.94(15)
C17 C18 H18 119.5
C9 C18 H18 119.5
C11 O1 C7 123.27(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.387(2)
C1 C2 1.388(2)
C1 H1 0.9300
C2 C3 1.369(3)
C2 H2 0.9300
C3 C4 1.370(3)
C3 H3 0.9300
C4 C5 1.373(3)
C4 H4 0.9300
C5 C6 1.394(2)
C5 H5 0.9300
C6 C7 1.474(2)
C7 C8 1.342(2)
C7 O1 1.3940(17)
C8 C9 1.452(2)
C8 C12 1.4945(19)
C9 C10 1.3990(19)
C9 C18 1.402(2)
C10 C15 1.395(2)
C10 C11 1.452(2)
C11 O2 1.2022(18)
C11 O1 1.3705(18)
C12 C14 1.485(2)
C12 C13 1.498(2)
C12 H12 0.9800
C13 C14 1.476(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.365(2)
C15 H15 0.9300
C16 C17 1.380(2)
C16 H16 0.9300
C17 C18 1.374(2)
C17 H17 0.9300
C18 H18 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
C6 C1 C2 C3 -1.0(2)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 0.9(3)
C3 C4 C5 C6 -2.0(2)
C2 C1 C6 C5 0.0(2)
C2 C1 C6 C7 -178.93(14)
C4 C5 C6 C1 1.5(2)
C4 C5 C6 C7 -179.57(14)
C1 C6 C7 C8 -48.2(2)
C5 C6 C7 C8 132.94(16)
C1 C6 C7 O1 132.61(14)
C5 C6 C7 O1 -46.30(17)
O1 C7 C8 C9 -1.35(19)
C6 C7 C8 C9 179.50(13)
O1 C7 C8 C12 178.44(12)
C6 C7 C8 C12 -0.7(2)
C7 C8 C9 C10 1.48(18)
C12 C8 C9 C10 -178.32(12)
C7 C8 C9 C18 -178.58(13)
C12 C8 C9 C18 1.61(19)
C18 C9 C10 C15 -1.14(19)
C8 C9 C10 C15 178.80(12)
C18 C9 C10 C11 178.20(12)
C8 C9 C10 C11 -1.86(19)
C15 C10 C11 O2 1.6(2)
C9 C10 C11 O2 -177.79(14)
C15 C10 C11 O1 -178.57(12)
C9 C10 C11 O1 2.07(19)
C7 C8 C12 C14 -45.2(2)
C9 C8 C12 C14 134.55(16)
C7 C8 C12 C13 -115.66(16)
C9 C8 C12 C13 64.14(18)
C8 C12 C13 C14 112.04(16)
C8 C12 C14 C13 -107.87(16)
C9 C10 C15 C16 0.0(2)
C11 C10 C15 C16 -179.39(13)
C10 C15 C16 C17 1.1(2)
C15 C16 C17 C18 -0.9(2)
C16 C17 C18 C9 -0.3(2)
C10 C9 C18 C17 1.3(2)
C8 C9 C18 C17 -178.62(13)
O2 C11 O1 C7 177.89(13)
C10 C11 O1 C7 -1.99(18)
C8 C7 O1 C11 1.7(2)
C6 C7 O1 C11 -178.98(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71531139
