#------------------------------------------------------------------------------
#$Date: 2021-02-03 22:29:34 +0200 (Wed, 03 Feb 2021) $
#$Revision: 261419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/84/4518476.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_4518476
loop_
_publ_author_name
'Kang, Guowei'
'Romo, Daniel'
_publ_section_title
;
 Photocatalyzed, β-Selective Hydrocarboxylation of α,β-Unsaturated
 Esters with CO2 under Flow for β-Lactone Synthesis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1309
_journal_page_last               1315
_journal_paper_doi               10.1021/acscatal.0c05050
_journal_year                    2021
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8509(3)
_cell_length_b                   22.6483(7)
_cell_length_c                   12.9093(3)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      3.16
_cell_volume                     2880.14(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27905
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.255
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0419
_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)+(0.0627P)²+1.0690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2992
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c05050_si_002.cif
_cod_data_source_block           DR52
_cod_database_code               4518476
_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   0.965
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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 0.53498(9) 0.69717(4) 0.62295(7) 0.0233(2) Uani 1 1 d . . . . .
O2 O 0.67799(10) 0.71643(4) 0.75279(7) 0.0254(2) Uani 1 1 d . . . . .
H1 H 0.603(2) 0.7096(9) 0.7904(17) 0.056(6) Uiso 1 1 d . . . . .
O3 O 0.63585(12) 0.82797(5) 0.59801(11) 0.0401(3) Uani 1 1 d . . . . .
O4 O 0.82845(11) 0.87670(4) 0.63073(9) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.77396(13) 0.71614(5) 0.58491(10) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.73826(14) 0.71549(6) 0.46897(10) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.6652 0.7446 0.4565 0.026 Uiso 1 1 calc R U . . .
H2B H 0.8189 0.7284 0.4292 0.026 Uiso 1 1 calc R U . . .
C3 C 0.69209(14) 0.65556(6) 0.42744(10) 0.0225(3) Uani 1 1 d . . . . .
H3A H 0.6785 0.6583 0.3516 0.027 Uiso 1 1 calc R U . . .
H3B H 0.6041 0.6449 0.4594 0.027 Uiso 1 1 calc R U . . .
C4 C 0.79632(14) 0.60736(6) 0.45085(10) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.8837 0.6191 0.4173 0.026 Uiso 1 1 calc R U . . .
C5 C 0.82053(14) 0.60528(6) 0.56842(10) 0.0222(3) Uani 1 1 d . . . . .
H5A H 0.7346 0.5952 0.6040 0.027 Uiso 1 1 calc R U . . .
H5B H 0.8877 0.5741 0.5845 0.027 Uiso 1 1 calc R U . . .
C6 C 0.87246(13) 0.66457(6) 0.60854(10) 0.0212(3) Uani 1 1 d . . . . .
H6A H 0.9616 0.6731 0.5764 0.025 Uiso 1 1 calc R U . . .
H6B H 0.8861 0.6619 0.6844 0.025 Uiso 1 1 calc R U . . .
C7 C 0.64919(13) 0.70933(5) 0.65349(10) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.84651(14) 0.77421(6) 0.61338(11) 0.0225(3) Uani 1 1 d . . . . .
H8A H 0.8862 0.7701 0.6835 0.027 Uiso 1 1 calc R U . . .
H8B H 0.9223 0.7805 0.5642 0.027 Uiso 1 1 calc R U . . .
C9 C 0.75630(14) 0.82800(6) 0.61200(10) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.75117(18) 0.93117(6) 0.63463(13) 0.0355(4) Uani 1 1 d . . . . .
H10A H 0.7191 0.9411 0.5649 0.053 Uiso 1 1 calc R U . . .
H10B H 0.8091 0.9631 0.6608 0.053 Uiso 1 1 calc R U . . .
H10C H 0.6731 0.9261 0.6808 0.053 Uiso 1 1 calc R U . . .
C11 C 0.75867(14) 0.54674(6) 0.41035(10) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.62493(16) 0.52737(7) 0.40450(13) 0.0335(4) Uani 1 1 d . . . . .
H12 H 0.5535 0.5533 0.4239 0.040 Uiso 1 1 calc R U . . .
C13 C 0.59434(17) 0.47062(8) 0.37074(14) 0.0389(4) Uani 1 1 d . . . . .
H13 H 0.5024 0.4580 0.3678 0.047 Uiso 1 1 calc R U . . .
C14 C 0.69693(18) 0.43235(7) 0.34138(13) 0.0366(4) Uani 1 1 d . . . . .
H14 H 0.6759 0.3936 0.3184 0.044 Uiso 1 1 calc R U . . .
C15 C 0.83026(17) 0.45115(7) 0.34578(13) 0.0339(4) Uani 1 1 d . . . . .
H15 H 0.9013 0.4253 0.3251 0.041 Uiso 1 1 calc R U . . .
C16 C 0.86072(15) 0.50769(7) 0.38040(11) 0.0281(3) Uani 1 1 d . . . . .
H16 H 0.9528 0.5200 0.3837 0.034 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H1 109.0(14) . . ?
C9 O4 C10 115.46(12) . . ?
C7 C1 C2 112.36(11) . . ?
C7 C1 C8 108.80(10) . . ?
C2 C1 C8 110.27(10) . . ?
C7 C1 C6 108.34(10) . . ?
C2 C1 C6 109.13(10) . . ?
C8 C1 C6 107.82(10) . . ?
C3 C2 C1 114.71(10) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 111.40(11) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C11 C4 C3 114.48(11) . . ?
C11 C4 C5 110.55(11) . . ?
C3 C4 C5 108.74(10) . . ?
C11 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C6 C5 C4 111.09(11) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 112.73(11) . . ?
C5 C6 H6A 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O1 C7 O2 122.48(12) . . ?
O1 C7 C1 125.29(11) . . ?
O2 C7 C1 112.21(11) . . ?
C9 C8 C1 114.41(11) . . ?
C9 C8 H8A 108.7 . . ?
C1 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C1 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O3 C9 O4 123.66(13) . . ?
O3 C9 C8 125.73(13) . . ?
O4 C9 C8 110.60(12) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.91(13) . . ?
C12 C11 C4 122.45(12) . . ?
C16 C11 C4 119.62(13) . . ?
C13 C12 C11 120.93(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.43(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.32(15) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.17(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.23(14) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
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 C7 1.2235(16) . ?
O2 C7 1.3227(15) . ?
O2 H1 0.90(2) . ?
O3 C9 1.2002(18) . ?
O4 C9 1.3343(17) . ?
O4 C10 1.4505(18) . ?
C1 C7 1.5227(18) . ?
C1 C2 1.5375(18) . ?
C1 C8 1.5412(17) . ?
C1 C6 1.5489(17) . ?
C2 C3 1.5286(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5288(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.5152(18) . ?
C4 C5 1.5371(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.5273(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.5080(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.391(2) . ?
C11 C16 1.3938(19) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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
O2 H1 O1 0.90(2) 1.78(2) 2.6768(14) 174(2) 3_656
