#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:28:52 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062089.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_7062089
loop_
_publ_author_name
'Chen, Li'
'Huang, Huangjiang'
'Luo, Benlong'
'Liu, Jinggong'
'Yang, Shuang'
'Fang, Xinqiang'
_publ_section_title
;
 Catalytic synthesis of seven-membered carbocycles via ring expansion of
 cyclic β-ketoesters
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              41
_journal_page_last               45
_journal_paper_doi               10.1039/D2NJ03473E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C21 H24 O7'
_chemical_formula_sum            'C21 H24 O7'
_chemical_formula_weight         388.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.598(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1896(3)
_cell_length_b                   5.80260(10)
_cell_length_c                   20.7903(4)
_cell_measurement_reflns_used    23888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4060
_cell_measurement_theta_min      2.4630
_cell_volume                     1941.15(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.510
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0397
_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)+(0.0545P)²+0.4410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3760
_reflns_number_total             4411
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03473e2.cif
_cod_data_source_block           cl-1_autored
_cod_depositor_comments
'Adding full bibliography for 7062089--7062092.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062089
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_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_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
O18 O 0.37219(5) 0.24428(14) 0.59140(4) 0.0188(2) Uani 1 1 d . . . . .
O28 O 0.28451(5) 0.74482(14) 0.74535(5) 0.0205(2) Uani 1 1 d . . . . .
H28 H 0.265467 0.682026 0.706528 0.031 Uiso 1 1 calc R U . . .
O22 O 0.40251(6) 0.02244(14) 0.68660(4) 0.0202(2) Uani 1 1 d . . . . .
O23 O 0.27765(5) 0.48590(15) 0.64846(4) 0.0207(2) Uani 1 1 d . . . . .
O25 O 0.58456(6) 0.06936(14) 0.93157(5) 0.0217(2) Uani 1 1 d . . . . .
O14 O 0.69348(6) 0.34704(16) 0.64191(5) 0.0243(2) Uani 1 1 d . . . . .
O27 O 0.63943(6) 0.41248(16) 0.92215(5) 0.0261(2) Uani 1 1 d . . . . .
C8 C 0.53686(7) 0.38015(19) 0.75614(6) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.47697(7) 0.39573(18) 0.79298(6) 0.0145(2) Uani 1 1 d . . . . .
C7 C 0.49481(7) 0.34079(18) 0.85955(6) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.39275(7) 0.48340(18) 0.75263(6) 0.0152(2) Uani 1 1 d . . . . .
C13 C 0.53639(7) 0.54820(19) 0.70764(6) 0.0171(2) Uani 1 1 d . . . . .
H13 H 0.499242 0.674943 0.700015 0.020 Uiso 1 1 calc R U . . .
C24 C 0.58068(8) 0.28405(19) 0.90630(6) 0.0160(2) Uani 1 1 d . . . . .
C17 C 0.37816(7) 0.19882(19) 0.65555(6) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.35771(7) 0.65843(18) 0.77973(6) 0.0168(2) Uani 1 1 d . . . . .
C11 C 0.64392(8) 0.3468(2) 0.68084(6) 0.0184(2) Uani 1 1 d . . . . .
C16 C 0.34652(7) 0.40399(19) 0.68546(6) 0.0161(2) Uani 1 1 d . . . . .
C9 C 0.59140(8) 0.19513(19) 0.76529(6) 0.0174(2) Uani 1 1 d . . . . .
H9 H 0.592005 0.078066 0.797410 0.021 Uiso 1 1 calc R U . . .
C12 C 0.58921(8) 0.5324(2) 0.67067(6) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.588245 0.648539 0.638190 0.024 Uiso 1 1 calc R U . . .
C10 C 0.64503(8) 0.1775(2) 0.72857(6) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.682142 0.050690 0.736055 0.023 Uiso 1 1 calc R U . . .
C6 C 0.42879(8) 0.3479(2) 0.89223(6) 0.0177(2) Uani 1 1 d . . . . .
H6A H 0.448016 0.257205 0.935315 0.021 Uiso 1 1 calc R U . . .
H6B H 0.377428 0.274850 0.860786 0.021 Uiso 1 1 calc R U . . .
C19 C 0.40053(8) 0.0653(2) 0.55504(7) 0.0205(3) Uani 1 1 d . . . . .
H19 H 0.454571 -0.000119 0.585960 0.025 Uiso 1 1 calc R U . . .
C4 C 0.40117(8) 0.7602(2) 0.84886(7) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.370585 0.899325 0.854039 0.026 Uiso 1 1 calc R U . . .
H4B H 0.457531 0.809136 0.851906 0.026 Uiso 1 1 calc R U . . .
C26 C 0.66508(8) -0.0032(2) 0.97806(7) 0.0256(3) Uani 1 1 d . . . . .
H26A H 0.706656 0.020378 0.956344 0.038 Uiso 1 1 calc R U . . .
H26B H 0.663030 -0.166921 0.988957 0.038 Uiso 1 1 calc R U . . .
H26C H 0.680201 0.087619 1.020438 0.038 Uiso 1 1 calc R U . . .
C15 C 0.75310(9) 0.1643(2) 0.65387(7) 0.0254(3) Uani 1 1 d . . . . .
H15A H 0.786628 0.186974 0.624788 0.038 Uiso 1 1 calc R U . . .
H15B H 0.724019 0.016246 0.642724 0.038 Uiso 1 1 calc R U . . .
H15C H 0.789379 0.164918 0.702287 0.038 Uiso 1 1 calc R U . . .
C5 C 0.40890(9) 0.5942(2) 0.90829(7) 0.0237(3) Uani 1 1 d . . . . .
H5A H 0.453422 0.649053 0.950313 0.028 Uiso 1 1 calc R U . . .
H5B H 0.356111 0.593865 0.917399 0.028 Uiso 1 1 calc R U . . .
C20 C 0.33624(9) -0.1234(2) 0.53204(7) 0.0269(3) Uani 1 1 d . . . . .
H20A H 0.329631 -0.196031 0.572367 0.040 Uiso 1 1 calc R U . . .
H20B H 0.354310 -0.239177 0.505957 0.040 Uiso 1 1 calc R U . . .
H20C H 0.283022 -0.057548 0.502863 0.040 Uiso 1 1 calc R U . . .
C21 C 0.41320(10) 0.1914(2) 0.49593(8) 0.0297(3) Uani 1 1 d . . . . .
H21A H 0.361229 0.266878 0.468167 0.045 Uiso 1 1 calc R U . . .
H21B H 0.429770 0.081357 0.467366 0.045 Uiso 1 1 calc R U . . .
H21C H 0.456820 0.307702 0.513913 0.045 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 0.0137 0.0067 '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 0.0389 0.0241 '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
C17 O18 C19 117.08(9) . . ?
C24 O25 C26 115.84(10) . . ?
C11 O14 C15 116.93(9) . . ?
C9 C8 C13 117.89(10) . . ?
C9 C8 C1 122.08(10) . . ?
C13 C8 C1 119.93(10) . . ?
C7 C1 C2 119.09(10) . . ?
C7 C1 C8 124.53(11) . . ?
C2 C1 C8 116.37(10) . . ?
C1 C7 C24 122.53(10) . . ?
C1 C7 C6 121.27(11) . . ?
C24 C7 C6 116.09(10) . . ?
C3 C2 C16 117.48(11) . . ?
C3 C2 C1 119.64(11) . . ?
C16 C2 C1 122.83(10) . . ?
C12 C13 C8 121.00(11) . . ?
O27 C24 O25 123.03(12) . . ?
O27 C24 C7 125.76(11) . . ?
O25 C24 C7 111.16(10) . . ?
O22 C17 O18 126.66(11) . . ?
O22 C17 C16 123.38(10) . . ?
O18 C17 C16 109.94(9) . . ?
O28 C3 C2 121.78(11) . . ?
O28 C3 C4 115.78(10) . . ?
C2 C3 C4 122.44(11) . . ?
O14 C11 C10 124.64(11) . . ?
O14 C11 C12 115.89(10) . . ?
C10 C11 C12 119.48(11) . . ?
O23 C16 C2 124.10(10) . . ?
O23 C16 C17 116.04(11) . . ?
C2 C16 C17 119.79(10) . . ?
C10 C9 C8 121.69(11) . . ?
C13 C12 C11 120.37(11) . . ?
C11 C10 C9 119.57(11) . . ?
C7 C6 C5 112.50(9) . . ?
O18 C19 C20 109.79(10) . . ?
O18 C19 C21 104.22(10) . . ?
C20 C19 C21 113.13(12) . . ?
C3 C4 C5 113.59(10) . . ?
C6 C5 C4 111.86(10) . . ?
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
O18 C17 1.3275(14) . ?
O18 C19 1.4652(13) . ?
O28 C3 1.3086(15) . ?
O22 C17 1.2039(14) . ?
O23 C16 1.2563(15) . ?
O25 C24 1.3445(14) . ?
O25 C26 1.4444(15) . ?
O14 C11 1.3662(14) . ?
O14 C15 1.4341(15) . ?
O27 C24 1.2041(15) . ?
C8 C9 1.3937(16) . ?
C8 C13 1.4007(16) . ?
C8 C1 1.4863(15) . ?
C1 C7 1.3463(16) . ?
C1 C2 1.4845(16) . ?
C7 C24 1.4908(17) . ?
C7 C6 1.5145(15) . ?
C2 C3 1.3966(15) . ?
C2 C16 1.4190(17) . ?
C13 C12 1.3837(16) . ?
C17 C16 1.5290(15) . ?
C3 C4 1.4889(18) . ?
C11 C10 1.3917(17) . ?
C11 C12 1.3964(16) . ?
C9 C10 1.3922(16) . ?
C6 C5 1.5335(16) . ?
C19 C20 1.5089(18) . ?
C19 C21 1.5104(18) . ?
C4 C5 1.5351(19) . ?
