#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/43/4034370.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_4034370
loop_
_publ_author_name
'John, Jubi'
'Omanakuttan, Vishnu K.'
'T, Aneeja'
'Suresh, Cherumuttathu H.'
'Jones, Peter G.'
'Hopf, Henning'
_publ_section_title
;
 Tandem α-Arylation/Cyclization of 4-Haloacetoacetates with Arynes: A
 Metal-Free Approach toward 4-Aryl-3-(2 H)-furanones.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5957
_journal_page_last               5964
_journal_paper_doi               10.1021/acs.joc.9b00488
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.935(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.6759(5)
_cell_length_b                   7.2560(2)
_cell_length_c                   19.3615(5)
_cell_measurement_reflns_used    16865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7563
_cell_measurement_theta_min      2.2634
_cell_volume                     2042.84(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47291
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.83
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+1.1945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                2814
_reflns_number_total             3099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00488_si_002.cif
_cod_data_source_block           kriep
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2042.82(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034370
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
O1 O 0.21885(4) 0.40430(9) 0.58166(3) 0.01646(14) Uani 1 1 d .
C2 C 0.12235(6) 0.36155(13) 0.54289(5) 0.01826(17) Uani 1 1 d .
H2A H 0.0838 0.4361 0.5628 0.022 Uiso 1 1 calc R
H2B H 0.1105 0.2294 0.5484 0.022 Uiso 1 1 calc R
C3 C 0.10156(6) 0.40875(11) 0.46174(5) 0.01562(16) Uani 1 1 d .
C4 C 0.18609(5) 0.47577(11) 0.45776(4) 0.01371(15) Uani 1 1 d .
C5 C 0.24914(6) 0.46772(11) 0.53023(4) 0.01384(16) Uani 1 1 d .
C6 C 0.39203(6) 0.50468(12) 0.63328(4) 0.01733(17) Uani 1 1 d .
H6A H 0.3953 0.3765 0.6516 0.021 Uiso 1 1 calc R
H6B H 0.3658 0.5840 0.6620 0.021 Uiso 1 1 calc R
C7 C 0.48580(6) 0.57206(15) 0.64074(5) 0.0245(2) Uani 1 1 d .
H7A H 0.5100 0.4938 0.6110 0.037 Uiso 1 1 calc R
H7B H 0.5273 0.5668 0.6931 0.037 Uiso 1 1 calc R
H7C H 0.4813 0.6995 0.6229 0.037 Uiso 1 1 calc R
O2 O 0.02448(4) 0.38970(10) 0.41282(4) 0.02100(15) Uani 1 1 d .
O3 O 0.33602(4) 0.51448(9) 0.55325(3) 0.01634(14) Uani 1 1 d .
C11 C 0.20166(5) 0.53992(11) 0.39137(4) 0.01359(15) Uani 1 1 d .
C12 C 0.28347(6) 0.62774(11) 0.39590(4) 0.01579(16) Uani 1 1 d .
H12 H 0.3312 0.6451 0.4432 0.019 Uiso 1 1 calc R
C13 C 0.29546(6) 0.68965(12) 0.33201(5) 0.01822(17) Uani 1 1 d .
H13 H 0.3511 0.7493 0.3362 0.022 Uiso 1 1 calc R
C14 C 0.22668(6) 0.66502(12) 0.26212(5) 0.01957(17) Uani 1 1 d .
H14 H 0.2350 0.7077 0.2187 0.023 Uiso 1 1 calc R
C15 C 0.14559(6) 0.57701(12) 0.25676(5) 0.01839(17) Uani 1 1 d .
H15 H 0.0985 0.5587 0.2092 0.022 Uiso 1 1 calc R
C16 C 0.13269(6) 0.51550(11) 0.32026(5) 0.01579(16) Uani 1 1 d .
H16 H 0.0767 0.4564 0.3156 0.019 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'
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
C5 O1 C2 106.31(6)
O1 C2 C3 105.46(6)
O2 C3 C4 130.83(8)
O2 C3 C2 122.60(8)
C4 C3 C2 106.56(7)
C5 C4 C3 104.75(7)
C5 C4 C11 127.66(7)
C3 C4 C11 127.58(7)
O3 C5 O1 116.74(7)
O3 C5 C4 126.33(7)
O1 C5 C4 116.92(7)
O3 C6 C7 105.24(7)
C5 O3 C6 118.81(6)
C12 C11 C16 117.87(7)
C12 C11 C4 122.31(7)
C16 C11 C4 119.81(7)
C13 C12 C11 120.90(7)
C14 C13 C12 120.63(8)
C13 C14 C15 119.08(8)
C14 C15 C16 120.76(8)
C15 C16 C11 120.75(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.3348(10)
O1 C2 1.4489(10)
C2 C3 1.5199(12)
C3 O2 1.2334(10)
C3 C4 1.4402(11)
C4 C5 1.3831(11)
C4 C11 1.4708(11)
C5 O3 1.3097(10)
C6 O3 1.4699(9)
C6 C7 1.5041(13)
C11 C12 1.4051(11)
C11 C16 1.4085(11)
C12 C13 1.3933(11)
C13 C14 1.3913(12)
C14 C15 1.3913(13)
C15 C16 1.3918(12)
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
C2 H2A O2 0.99 2.30 3.2810(11) 169.7 5_566
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 O1 C2 C3 0.22(8)
O1 C2 C3 O2 -179.56(8)
O1 C2 C3 C4 -0.05(9)
O2 C3 C4 C5 179.32(9)
C2 C3 C4 C5 -0.13(8)
O2 C3 C4 C11 -0.26(15)
C2 C3 C4 C11 -179.71(8)
C2 O1 C5 O3 -179.64(7)
C2 O1 C5 C4 -0.34(9)
C3 C4 C5 O3 179.53(8)
C11 C4 C5 O3 -0.89(14)
C3 C4 C5 O1 0.30(9)
C11 C4 C5 O1 179.88(7)
O1 C5 O3 C6 -3.53(10)
C4 C5 O3 C6 177.24(8)
C7 C6 O3 C5 -178.30(7)
C5 C4 C11 C12 -9.17(13)
C3 C4 C11 C12 170.32(8)
C5 C4 C11 C16 171.49(8)
C3 C4 C11 C16 -9.03(12)
C16 C11 C12 C13 0.44(12)
C4 C11 C12 C13 -178.92(8)
C11 C12 C13 C14 -0.30(13)
C12 C13 C14 C15 -0.19(13)
C13 C14 C15 C16 0.53(13)
C14 C15 C16 C11 -0.39(13)
C12 C11 C16 C15 -0.10(12)
C4 C11 C16 C15 179.28(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328279
