#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/53/1555307.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_1555307
loop_
_publ_author_name
'Gao, Bao'
'Xie, Yinjun'
'Shen, Zhiqiang'
'Yang, Lei'
'Huang, Hanmin'
_publ_section_title
;
 Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by
 Copper-Catalyzed Oxidative Coupling.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4968
_journal_page_last               4971
_journal_paper_doi               10.1021/acs.orglett.5b02382
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.34
_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_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.1000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1900(11)
_cell_length_b                   10.5762(9)
_cell_length_c                   12.1985(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1608.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7986
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0411
_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)+(0.0770P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                2360
_reflns_number_total             2838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02382_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1555307
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
O1 O 0.47900(8) 0.67640(11) 0.08246(9) 0.0568(3) Uani 1 1 d .
O2 O 0.40400(10) 0.91361(11) 0.06927(11) 0.0667(4) Uani 1 1 d .
O3 O -0.14741(10) 0.64434(12) 0.19912(12) 0.0759(4) Uani 1 1 d .
O4 O -0.14105(11) 0.85194(13) 0.18227(13) 0.0830(4) Uani 1 1 d .
O5 O 0.39284(9) 0.48908(10) 0.16780(10) 0.0593(3) Uani 1 1 d .
C1 C 0.35569(12) 0.82597(15) 0.11801(13) 0.0515(4) Uani 1 1 d .
C2 C 0.27354(12) 0.85181(15) 0.16225(14) 0.0530(4) Uani 1 1 d .
H2 H 0.2481 0.9341 0.1603 0.064 Uiso 1 1 calc R
C3 C 0.22892(12) 0.75616(14) 0.20944(13) 0.0488(4) Uani 1 1 d .
C4 C 0.26750(12) 0.63244(15) 0.21327(13) 0.0487(4) Uani 1 1 d .
H4 H 0.2382 0.5680 0.2453 0.058 Uiso 1 1 calc R
C5 C 0.34965(11) 0.60630(14) 0.16916(12) 0.0464(4) Uani 1 1 d .
C6 C 0.39438(11) 0.70245(15) 0.12142(12) 0.0472(4) Uani 1 1 d .
C7 C 0.44775(15) 0.66059(19) -0.04039(15) 0.0648(5) Uani 1 1 d .
H7A H 0.3983 0.5913 -0.0636 0.097 Uiso 1 1 calc R
H7B H 0.5100 0.6433 -0.0622 0.097 Uiso 1 1 calc R
H7C H 0.4139 0.7365 -0.0780 0.097 Uiso 1 1 calc R
C8 C 0.35806(15) 0.38939(16) 0.22441(17) 0.0660(5) Uani 1 1 d .
H8A H 0.3695 0.4124 0.3037 0.099 Uiso 1 1 calc R
H8B H 0.3980 0.3142 0.2220 0.099 Uiso 1 1 calc R
H8C H 0.2831 0.3740 0.1859 0.099 Uiso 1 1 calc R
C9 C 0.3764(2) 1.04209(19) 0.0737(2) 0.0902(7) Uani 1 1 d .
H9A H 0.3024 1.0543 0.0284 0.135 Uiso 1 1 calc R
H9B H 0.4207 1.0936 0.0431 0.135 Uiso 1 1 calc R
H9C H 0.3873 1.0657 0.1528 0.135 Uiso 1 1 calc R
C10 C 0.14197(13) 0.78858(15) 0.25571(14) 0.0536(4) Uani 1 1 d .
H10 H 0.1254 0.8741 0.2555 0.064 Uiso 1 1 calc R
C11 C 0.08574(12) 0.71276(15) 0.29662(15) 0.0525(4) Uani 1 1 d .
H11 H 0.1032 0.6274 0.2993 0.063 Uiso 1 1 calc R
C12 C -0.00587(12) 0.74885(14) 0.34079(13) 0.0483(4) Uani 1 1 d .
C13 C 0.01231(16) 0.87699(18) 0.40224(18) 0.0699(5) Uani 1 1 d .
H13A H 0.0785 0.8751 0.4659 0.105 Uiso 1 1 calc R
H13B H -0.0459 0.8945 0.4309 0.105 Uiso 1 1 calc R
H13C H 0.0158 0.9418 0.3485 0.105 Uiso 1 1 calc R
C14 C -0.01792(16) 0.64585(19) 0.42405(16) 0.0696(5) Uani 1 1 d .
H14A H -0.0232 0.5647 0.3873 0.104 Uiso 1 1 calc R
H14B H -0.0816 0.6613 0.4437 0.104 Uiso 1 1 calc R
H14C H 0.0435 0.6470 0.4933 0.104 Uiso 1 1 calc R
C15 C -0.10521(12) 0.75678(14) 0.23348(14) 0.0500(4) Uani 1 1 d .
C16 C -0.23908(19) 0.6404(3) 0.0936(2) 0.1004(8) Uani 1 1 d .
H16A H -0.3026 0.6643 0.1106 0.151 Uiso 1 1 calc R
H16B H -0.2475 0.5563 0.0623 0.151 Uiso 1 1 calc R
H16C H -0.2279 0.6981 0.0379 0.151 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
C6 O1 C7 113.43(12)
C1 O2 C9 118.24(14)
C15 O3 C16 116.71(16)
C5 O5 C8 117.81(12)
O2 C1 C2 124.80(14)
O2 C1 C6 115.42(13)
C2 C1 C6 119.78(14)
C1 C2 C3 120.64(14)
C1 C2 H2 119.7
C3 C2 H2 119.7
C2 C3 C4 119.80(14)
C2 C3 C10 118.56(13)
C4 C3 C10 121.63(14)
C5 C4 C3 119.70(14)
C5 C4 H4 120.2
C3 C4 H4 120.2
O5 C5 C4 124.58(14)
O5 C5 C6 114.91(12)
C4 C5 C6 120.51(14)
O1 C6 C5 119.98(13)
O1 C6 C1 120.40(13)
C5 C6 C1 119.57(13)
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O5 C8 H8A 109.5
O5 C8 H8B 109.5
H8A C8 H8B 109.5
O5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 H9A 109.5
O2 C9 H9B 109.5
H9A C9 H9B 109.5
O2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C3 128.12(15)
C11 C10 H10 115.9
C3 C10 H10 115.9
C10 C11 C12 126.88(14)
C10 C11 H11 116.6
C12 C11 H11 116.6
C15 C12 C11 105.60(12)
C15 C12 C13 109.01(14)
C11 C12 C13 112.33(13)
C15 C12 C14 111.25(13)
C11 C12 C14 108.81(13)
C13 C12 C14 109.80(14)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O4 C15 O3 122.52(16)
O4 C15 C12 125.25(15)
O3 C15 C12 112.21(13)
O3 C16 H16A 109.5
O3 C16 H16B 109.5
H16A C16 H16B 109.5
O3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.3765(17)
O1 C7 1.428(2)
O2 C1 1.3664(19)
O2 C9 1.412(2)
O3 C15 1.3218(19)
O3 C16 1.450(2)
O4 C15 1.1972(19)
O5 C5 1.3667(18)
O5 C8 1.416(2)
C1 C2 1.387(2)
C1 C6 1.398(2)
C2 C3 1.387(2)
C2 H2 0.9300
C3 C4 1.399(2)
C3 C10 1.475(2)
C4 C5 1.386(2)
C4 H4 0.9300
C5 C6 1.395(2)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.298(2)
C10 H10 0.9300
C11 C12 1.524(2)
C11 H11 0.9300
C12 C15 1.522(2)
C12 C13 1.529(2)
C12 C14 1.533(2)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
C9 O2 C1 C2 6.5(3)
C9 O2 C1 C6 -173.67(17)
O2 C1 C2 C3 179.55(15)
C6 C1 C2 C3 -0.3(2)
C1 C2 C3 C4 0.4(2)
C1 C2 C3 C10 179.80(14)
C2 C3 C4 C5 -0.4(2)
C10 C3 C4 C5 -179.75(14)
C8 O5 C5 C4 -5.8(2)
C8 O5 C5 C6 174.32(14)
C3 C4 C5 O5 -179.57(14)
C3 C4 C5 C6 0.2(2)
C7 O1 C6 C5 99.98(16)
C7 O1 C6 C1 -82.73(18)
O5 C5 C6 O1 -2.97(19)
C4 C5 C6 O1 177.20(13)
O5 C5 C6 C1 179.72(13)
C4 C5 C6 C1 -0.1(2)
O2 C1 C6 O1 3.0(2)
C2 C1 C6 O1 -177.16(13)
O2 C1 C6 C5 -179.72(13)
C2 C1 C6 C5 0.1(2)
C2 C3 C10 C11 175.48(17)
C4 C3 C10 C11 -5.2(3)
C3 C10 C11 C12 -178.16(15)
C10 C11 C12 C15 83.54(19)
C10 C11 C12 C13 -35.2(2)
C10 C11 C12 C14 -156.94(17)
C16 O3 C15 O4 1.3(3)
C16 O3 C15 C12 -176.65(17)
C11 C12 C15 O4 -96.88(18)
C13 C12 C15 O4 24.0(2)
C14 C12 C15 O4 145.23(17)
C11 C12 C15 O3 81.05(16)
C13 C12 C15 O3 -158.06(14)
C14 C12 C15 O3 -36.84(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305095
