#------------------------------------------------------------------------------
#$Date: 2017-11-06 01:06:49 +0200 (Mon, 06 Nov 2017) $
#$Revision: 202609 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/30/4033055.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_4033055
loop_
_publ_author_name
'Sha, Wanxing'
'Zhang, Wenzhong'
'Ni, Shengyang'
'Mei, Haibo'
'Han, Jianlin'
'Pan, Yi'
_publ_section_title
;
 Photoredox-Catalyzed Cascade Difluoroalkylation and Intramolecular
 Cyclization for Construction of Fluorinated γ-Butyrolactones.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9824
_journal_page_last               9831
_journal_paper_doi               10.1021/acs.joc.7b01279
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C13 H12 F2 O4'
_chemical_formula_weight         270.23
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.996(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9502(16)
_cell_length_b                   7.9101(9)
_cell_length_c                   11.5513(15)
_cell_measurement_reflns_used    4495
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.02
_cell_volume                     1231.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8495
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         3.023
_exptl_absorpt_coefficient_mu    0.127
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description
;
;
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1853
_reflns_number_total             2159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01279_si_002.cif
_cod_data_source_block           2_a
_cod_database_code               4033055
_shelx_shelxl_version_number     2014/7
_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   0.969
_shelx_estimated_absorpt_t_max   0.976
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
C1 C 0.83793(10) 0.45710(18) 0.41512(14) 0.0226(3) Uani 1 1 d . .
C2 C 0.82944(11) 0.6233(2) 0.37604(16) 0.0315(4) Uani 1 1 d . .
H2 H 0.7995 0.6502 0.2965 0.038 Uiso 1 1 calc R U
C3 C 0.86719(12) 0.7477(2) 0.45964(18) 0.0384(4) Uani 1 1 d . .
H3 H 0.8622 0.8604 0.4358 0.046 Uiso 1 1 calc R U
C4 C 0.91245(12) 0.7079(2) 0.57862(18) 0.0383(4) Uani 1 1 d . .
H4 H 0.9368 0.7942 0.6329 0.046 Uiso 1 1 calc R U
C5 C 0.92171(11) 0.5423(2) 0.61709(15) 0.0314(4) Uani 1 1 d . .
H5 H 0.9519 0.5147 0.6964 0.038 Uiso 1 1 calc R U
C6 C 0.88411(10) 0.41862(19) 0.53249(13) 0.0236(3) Uani 1 1 d . .
C7 C 0.88482(11) 0.2340(2) 0.54602(13) 0.0248(3) Uani 1 1 d . .
C8 C 0.80538(11) 0.29594(18) 0.34786(13) 0.0234(3) Uani 1 1 d . .
H8 H 0.8379 0.2834 0.2826 0.028 Uiso 1 1 calc R U
C9 C 0.69281(11) 0.28254(19) 0.29926(13) 0.0257(4) Uani 1 1 d . .
H9A H 0.6636 0.2643 0.3659 0.031 Uiso 1 1 calc R U
H9B H 0.6677 0.3892 0.2621 0.031 Uiso 1 1 calc R U
C10 C 0.65954(12) 0.1428(2) 0.20922(14) 0.0299(4) Uani 1 1 d . .
C11 C 0.54629(12) 0.1225(2) 0.17197(14) 0.0315(4) Uani 1 1 d . .
C12 C 0.39721(11) 0.2369(2) 0.05153(16) 0.0380(4) Uani 1 1 d . .
H12A H 0.3734 0.2634 0.1213 0.046 Uiso 1 1 calc R U
H12B H 0.3686 0.1300 0.0187 0.046 Uiso 1 1 calc R U
C13 C 0.36896(14) 0.3732(3) -0.0398(2) 0.0568(6) Uani 1 1 d . .
H13A H 0.3983 0.4780 -0.0064 0.085 Uiso 1 1 calc R U
H13B H 0.2980 0.3846 -0.0634 0.085 Uiso 1 1 calc R U
H13C H 0.3923 0.3449 -0.1086 0.085 Uiso 1 1 calc R U
F1 F 0.69924(7) -0.00839(12) 0.25322(10) 0.0452(3) Uani 1 1 d . .
F2 F 0.69302(7) 0.17191(14) 0.10975(9) 0.0427(3) Uani 1 1 d . .
O1 O 0.83929(8) 0.16498(12) 0.43745(9) 0.0275(3) Uani 1 1 d . .
O2 O 0.91706(9) 0.14620(15) 0.63240(10) 0.0362(3) Uani 1 1 d . .
O3 O 0.50356(10) 0.0293(2) 0.22286(14) 0.0593(4) Uani 1 1 d . .
O4 O 0.50599(8) 0.22684(15) 0.08468(10) 0.0338(3) Uani 1 1 d . .
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'
F F 0.0171 0.0103 '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 C1 C2 120.65(14)
C6 C1 C8 108.90(13)
C2 C1 C8 130.43(14)
C3 C2 C1 117.56(16)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 121.43(16)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 120.92(16)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 117.15(16)
C4 C5 H5 121.4
C6 C5 H5 121.4
C1 C6 C5 122.27(15)
C1 C6 C7 108.26(13)
C5 C6 C7 129.47(14)
O2 C7 O1 121.12(14)
O2 C7 C6 130.75(15)
O1 C7 C6 108.13(12)
O1 C8 C1 103.74(11)
O1 C8 C9 109.03(12)
C1 C8 C9 113.17(12)
O1 C8 H8 110.2
C1 C8 H8 110.2
C9 C8 H8 110.2
C10 C9 C8 114.09(13)
C10 C9 H9A 108.7
C8 C9 H9A 108.7
C10 C9 H9B 108.7
C8 C9 H9B 108.7
H9A C9 H9B 107.6
F1 C10 F2 105.52(13)
F1 C10 C9 111.36(12)
F2 C10 C9 110.21(13)
F1 C10 C11 107.63(13)
F2 C10 C11 109.44(12)
C9 C10 C11 112.41(13)
O3 C11 O4 126.70(16)
O3 C11 C10 122.37(15)
O4 C11 C10 110.81(13)
O4 C12 C13 106.88(14)
O4 C12 H12A 110.3
C13 C12 H12A 110.3
O4 C12 H12B 110.3
C13 C12 H12B 110.3
H12A C12 H12B 108.6
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
C7 O1 C8 110.96(11)
C11 O4 C12 116.31(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.376(2)
C1 C2 1.385(2)
C1 C8 1.501(2)
C2 C3 1.384(2)
C2 H2 0.9300
C3 C4 1.392(3)
C3 H3 0.9300
C4 C5 1.379(3)
C4 H4 0.9300
C5 C6 1.386(2)
C5 H5 0.9300
C6 C7 1.469(2)
C7 O2 1.2031(18)
C7 O1 1.3645(18)
C8 O1 1.4541(17)
C8 C9 1.528(2)
C8 H8 0.9800
C9 C10 1.506(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 F1 1.3600(19)
C10 F2 1.3670(19)
C10 C11 1.535(2)
C11 O3 1.194(2)
C11 O4 1.312(2)
C12 O4 1.4680(19)
C12 C13 1.489(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
