#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:34:24 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284940 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062509.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_7062509
loop_
_publ_author_name
'Zhang, Mingshuai'
'Chen, Longkun'
'Liu, Donghan'
'Liu, Zhuoyuan'
'Huang, Jiuzhong'
'Li, Xiang'
'Yu, Fuchao'
_publ_section_title
;
 Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones
 with iodonium ylides to give substituted isocoumarins
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12274
_journal_page_last               12278
_journal_paper_doi               10.1039/D3NJ02073H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-24 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.149(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6765(5)
_cell_length_b                   13.7501(6)
_cell_length_c                   10.5137(5)
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8060
_cell_measurement_theta_min      5.5510
_cell_volume                     1350.27(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4661
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.240
_diffrn_reflns_theta_max         67.240
_diffrn_reflns_theta_min         5.418
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0717P)²+0.2028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             2415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02073h2.cif
_cod_data_source_block           exp_12923
_cod_depositor_comments          'Adding full bibliography for 7062509.cif.'
_cod_original_cell_volume        1350.27(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062509
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.858
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21636(15) 0.64646(9) 0.87028(13) 0.0575(4) Uani 1 1 d . . . . .
O2 O 0.53517(15) 0.94035(11) 1.31748(13) 0.0648(4) Uani 1 1 d . . . . .
O3 O 0.41528(13) 1.04205(9) 1.16718(11) 0.0488(3) Uani 1 1 d . . . . .
O4 O 0.13066(18) 0.96622(10) 0.73906(14) 0.0716(5) Uani 1 1 d . . . . .
C1 C 0.28050(18) 0.71609(12) 0.95676(17) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.3629(2) 0.69706(14) 1.08390(19) 0.0496(4) Uani 1 1 d . . . . .
H2 H 0.379882 0.633551 1.114423 0.059 Uiso 1 1 calc R U . . .
C3 C 0.41853(19) 0.77434(14) 1.16295(17) 0.0491(4) Uani 1 1 d . . . . .
H3 H 0.474910 0.762575 1.247774 0.059 Uiso 1 1 calc R U . . .
C4 C 0.39305(17) 0.86994(13) 1.11994(16) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.45430(18) 0.94761(14) 1.20984(17) 0.0465(4) Uani 1 1 d . . . . .
C6 C 0.33041(17) 1.06173(12) 1.04435(16) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.30373(19) 1.16792(12) 1.02758(17) 0.0459(4) Uani 1 1 d . . . . .
H7A H 0.386229 1.198549 1.008222 0.055 Uiso 1 1 calc R U . . .
H7B H 0.293249 1.194837 1.109830 0.055 Uiso 1 1 calc R U . . .
C8 C 0.17019(19) 1.19251(12) 0.91767(18) 0.0452(4) Uani 1 1 d . . . . .
C9 C 0.1753(2) 1.13118(12) 0.79730(17) 0.0464(4) Uani 1 1 d . . . . .
H9A H 0.088579 1.142864 0.728021 0.056 Uiso 1 1 calc R U . . .
H9B H 0.255561 1.152664 0.765258 0.056 Uiso 1 1 calc R U . . .
C10 C 0.18947(18) 1.02370(12) 0.82374(16) 0.0423(4) Uani 1 1 d . . . . .
C11 C 0.27922(16) 0.99141(12) 0.95417(15) 0.0367(4) Uani 1 1 d . . . . .
C12 C 0.30925(16) 0.88955(12) 0.99123(15) 0.0356(4) Uani 1 1 d . . . . .
C13 C 0.25620(17) 0.81079(11) 0.91005(15) 0.0395(4) Uani 1 1 d . . . . .
H13 H 0.203893 0.821634 0.823551 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2223(3) 0.54786(13) 0.9157(2) 0.0673(6) Uani 1 1 d . . . . .
H14A H 0.320235 0.526998 0.943240 0.101 Uiso 1 1 calc R U . . .
H14B H 0.170366 0.506785 0.845487 0.101 Uiso 1 1 calc R U . . .
H14C H 0.180099 0.543750 0.988617 0.101 Uiso 1 1 calc R U . . .
C15 C 0.0350(2) 1.16861(16) 0.9608(2) 0.0624(5) Uani 1 1 d . . . . .
H15A H 0.032953 1.206957 1.036537 0.094 Uiso 1 1 calc R U . . .
H15B H 0.035050 1.100824 0.982608 0.094 Uiso 1 1 calc R U . . .
H15C H -0.047822 1.183036 0.890203 0.094 Uiso 1 1 calc R U . . .
C16 C 0.1721(3) 1.30076(14) 0.8854(2) 0.0669(6) Uani 1 1 d . . . . .
H16A H 0.088288 1.316777 0.816747 0.100 Uiso 1 1 calc R U . . .
H16B H 0.256112 1.315260 0.856452 0.100 Uiso 1 1 calc R U . . .
H16C H 0.173264 1.338266 0.962662 0.100 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C14 118.29(15) . . ?
C6 O3 C5 122.35(13) . . ?
O1 C1 C13 114.81(15) . . ?
O1 C1 C2 124.02(16) . . ?
C13 C1 C2 121.16(16) . . ?
C3 C2 C1 118.22(16) . . ?
C2 C3 C4 121.86(16) . . ?
C3 C4 C12 120.09(16) . . ?
C3 C4 C5 118.54(15) . . ?
C12 C4 C5 121.37(16) . . ?
O2 C5 O3 115.86(16) . . ?
O2 C5 C4 127.56(18) . . ?
O3 C5 C4 116.58(14) . . ?
C11 C6 O3 122.73(15) . . ?
C11 C6 C7 126.76(15) . . ?
O3 C6 C7 110.51(14) . . ?
C6 C7 C8 113.16(14) . . ?
C15 C8 C16 109.68(16) . . ?
C15 C8 C7 110.38(16) . . ?
C16 C8 C7 109.03(16) . . ?
C15 C8 C9 109.96(15) . . ?
C16 C8 C9 110.35(16) . . ?
C7 C8 C9 107.41(14) . . ?
C10 C9 C8 114.17(14) . . ?
O4 C10 C11 122.05(15) . . ?
O4 C10 C9 120.09(15) . . ?
C11 C10 C9 117.86(14) . . ?
C6 C11 C12 119.11(14) . . ?
C6 C11 C10 116.83(15) . . ?
C12 C11 C10 124.01(14) . . ?
C13 C12 C4 117.86(15) . . ?
C13 C12 C11 124.49(14) . . ?
C4 C12 C11 117.60(15) . . ?
C1 C13 C12 120.75(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.354(2) . ?
O1 C14 1.433(2) . ?
O2 C5 1.200(2) . ?
O3 C6 1.364(2) . ?
O3 C5 1.393(2) . ?
O4 C10 1.215(2) . ?
C1 C13 1.390(2) . ?
C1 C2 1.391(2) . ?
C2 C3 1.369(3) . ?
C3 C4 1.391(3) . ?
C4 C12 1.410(2) . ?
C4 C5 1.447(3) . ?
C6 C11 1.354(2) . ?
C6 C7 1.485(2) . ?
C7 C8 1.529(2) . ?
C8 C15 1.527(3) . ?
C8 C16 1.528(3) . ?
C8 C9 1.532(2) . ?
C9 C10 1.503(2) . ?
C10 C11 1.486(2) . ?
C11 C12 1.462(2) . ?
C12 C13 1.391(2) . ?
