#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:02:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180285 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117130.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_7117130
loop_
_publ_author_name
'Jieru Yang'
'Ao Mao'
'Zhenting Yue'
'Wenxuan Zhu'
'Xuewei Luo'
'Chuwei Zhu'
'Yuanjing Xiao'
'Junliang Zhang'
_publ_section_title
;
 A simple base-mediated synthesis of diverse functionalized
 ring-fluorinated 4H-pyrans via double direct C-F substitutions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8326
_journal_paper_doi               10.1039/C5cc02073E
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C27 H21 Br O5'
_chemical_formula_weight         505.35
_chemical_name_systematic
'ethyl 5-benzoyl-4-(4-bromophenyl)-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-3-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-10 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0879(3)
_cell_length_b                   27.2026(11)
_cell_length_c                   10.7134(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2352.99(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27224
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.7515
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.044
_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     298
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0356P)²+1.8737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                3221
_reflns_number_total             4160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02073e2.cif
_cod_data_source_block           z
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7117130
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89323(4) 0.223106(13) 0.39839(4) 0.07213(15) Uani 1 1 d . . .
O1 O 1.8408(3) 0.06861(8) 0.5201(2) 0.0625(5) Uani 1 1 d . . .
O2 O 1.7330(2) 0.01506(7) 0.65205(18) 0.0553(5) Uani 1 1 d . . .
O3 O 1.7244(3) 0.21614(7) 0.7039(2) 0.0668(6) Uani 1 1 d . . .
O4 O 1.3365(3) 0.02098(7) 0.62113(18) 0.0581(5) Uani 1 1 d . . .
O5 O 1.4475(2) 0.06888(6) 0.76779(15) 0.0428(4) Uani 1 1 d . . .
C1 C 1.3995(3) 0.15541(9) 0.5430(2) 0.0380(6) Uani 1 1 d . . .
C2 C 1.3509(4) 0.15589(12) 0.4173(2) 0.0594(8) Uani 1 1 d . . .
H2A H 1.4209 0.1424 0.3605 0.071 Uiso 1 1 calc R . .
C3 C 1.2016(4) 0.17576(12) 0.3734(3) 0.0623(9) Uani 1 1 d . . .
H3A H 1.1710 0.1756 0.2883 0.075 Uiso 1 1 calc R . .
C4 C 1.1002(3) 0.19557(10) 0.4569(3) 0.0474(7) Uani 1 1 d . . .
C5 C 1.1450(4) 0.19705(12) 0.5817(3) 0.0550(7) Uani 1 1 d . . .
H5A H 1.0758 0.2115 0.6375 0.066 Uiso 1 1 calc R . .
C6 C 1.2951(3) 0.17681(10) 0.6239(2) 0.0497(7) Uani 1 1 d . . .
H6A H 1.3259 0.1777 0.7089 0.060 Uiso 1 1 calc R . .
C7 C 1.5938(3) 0.10484(9) 0.9413(2) 0.0390(6) Uani 1 1 d . . .
C8 C 1.6039(3) 0.14776(11) 1.0103(2) 0.0487(7) Uani 1 1 d . . .
H8A H 1.5826 0.1778 0.9713 0.058 Uiso 1 1 calc R . .
C9 C 1.6454(4) 0.14608(14) 1.1370(3) 0.0654(9) Uani 1 1 d . . .
H9A H 1.6537 0.1751 1.1829 0.078 Uiso 1 1 calc R . .
C10 C 1.6746(4) 0.10192(16) 1.1955(3) 0.0721(10) Uani 1 1 d . . .
H10A H 1.7045 0.1011 1.2806 0.087 Uiso 1 1 calc R . .
C11 C 1.6597(4) 0.05892(14) 1.1289(3) 0.0695(9) Uani 1 1 d . . .
H11A H 1.6772 0.0289 1.1691 0.083 Uiso 1 1 calc R . .
C12 C 1.6188(3) 0.06024(11) 1.0020(3) 0.0532(7) Uani 1 1 d . . .
H12A H 1.6080 0.0311 0.9570 0.064 Uiso 1 1 calc R . .
C13 C 1.8887(3) 0.16587(10) 0.8394(2) 0.0427(6) Uani 1 1 d . . .
C14 C 1.9536(4) 0.20322(12) 0.9159(3) 0.0574(8) Uani 1 1 d . . .
H14A H 1.9062 0.2344 0.9118 0.069 Uiso 1 1 calc R . .
C15 C 2.0880(4) 0.19432(15) 0.9977(3) 0.0712(10) Uani 1 1 d . . .
H15A H 2.1280 0.2190 1.0514 0.085 Uiso 1 1 calc R . .
C16 C 2.1624(4) 0.14930(17) 1.0000(3) 0.0743(10) Uani 1 1 d . . .
H16A H 2.2540 0.1436 1.0546 0.089 Uiso 1 1 calc R . .
C17 C 2.1032(4) 0.11255(14) 0.9225(3) 0.0689(9) Uani 1 1 d . . .
H17A H 2.1562 0.0822 0.9231 0.083 Uiso 1 1 calc R . .
C18 C 1.9647(3) 0.12045(11) 0.8433(3) 0.0524(7) Uani 1 1 d . . .
H18A H 1.9227 0.0951 0.7925 0.063 Uiso 1 1 calc R . .
C19 C 1.5609(3) 0.10581(9) 0.8045(2) 0.0369(6) Uani 1 1 d . . .
C20 C 1.6195(3) 0.13651(9) 0.7211(2) 0.0360(5) Uani 1 1 d . . .
C21 C 1.5630(3) 0.13071(9) 0.5839(2) 0.0382(6) Uani 1 1 d . . .
H21A H 1.6493 0.1443 0.5335 0.046 Uiso 1 1 calc R . .
C22 C 1.5539(3) 0.07491(9) 0.5603(2) 0.0404(6) Uani 1 1 d . . .
H22A H 1.5095 0.0696 0.4743 0.048 Uiso 1 1 calc R . .
C23 C 1.4373(3) 0.05189(10) 0.6472(2) 0.0422(6) Uani 1 1 d . . .
C24 C 1.7272(4) 0.05286(10) 0.5733(2) 0.0456(6) Uani 1 1 d . . .
C25 C 1.8881(4) -0.01232(13) 0.6657(3) 0.0756(10) Uani 1 1 d . . .
H25A H 1.9812 0.0101 0.6757 0.091 Uiso 1 1 calc R . .
H25B H 1.9020 -0.0325 0.5923 0.091 Uiso 1 1 calc R . .
C26 C 1.8788(6) -0.04322(18) 0.7766(5) 0.1229(18) Uani 1 1 d . . .
H26A H 1.9795 -0.0617 0.7894 0.184 Uiso 1 1 calc R . .
H26B H 1.7869 -0.0654 0.7651 0.184 Uiso 1 1 calc R . .
H26C H 1.8640 -0.0229 0.8483 0.184 Uiso 1 1 calc R . .
C27 C 1.7416(3) 0.17610(9) 0.7531(2) 0.0425(6) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C24 O2 C25 117.1(2) . .
C23 O5 C19 120.61(19) . .
C6 C1 C2 117.5(2) . .
C6 C1 C21 124.1(2) . .
C2 C1 C21 118.5(2) . .
C3 C2 C1 121.9(3) . .
C3 C2 H2A 119.0 . .
C1 C2 H2A 119.0 . .
C4 C3 C2 118.7(3) . .
C4 C3 H3A 120.6 . .
C2 C3 H3A 120.6 . .
C3 C4 C5 121.3(3) . .
C3 C4 Br1 119.4(2) . .
C5 C4 Br1 119.2(2) . .
C4 C5 C6 119.1(3) . .
C4 C5 H5A 120.5 . .
C6 C5 H5A 120.5 . .
C1 C6 C5 121.4(2) . .
C1 C6 H6A 119.3 . .
C5 C6 H6A 119.3 . .
C8 C7 C12 119.1(2) . .
C8 C7 C19 121.2(2) . .
C12 C7 C19 119.6(2) . .
C9 C8 C7 120.1(3) . .
C9 C8 H8A 120.0 . .
C7 C8 H8A 120.0 . .
C10 C9 C8 120.3(3) . .
C10 C9 H9A 119.8 . .
C8 C9 H9A 119.8 . .
C9 C10 C11 120.2(3) . .
C9 C10 H10A 119.9 . .
C11 C10 H10A 119.9 . .
C10 C11 C12 119.9(3) . .
C10 C11 H11A 120.0 . .
C12 C11 H11A 120.0 . .
C11 C12 C7 120.3(3) . .
C11 C12 H12A 119.9 . .
C7 C12 H12A 119.9 . .
C18 C13 C14 119.0(3) . .
C18 C13 C27 121.6(2) . .
C14 C13 C27 119.4(3) . .
C15 C14 C13 120.3(3) . .
C15 C14 H14A 119.9 . .
C13 C14 H14A 119.9 . .
C16 C15 C14 120.0(3) . .
C16 C15 H15A 120.0 . .
C14 C15 H15A 120.0 . .
C15 C16 C17 120.4(3) . .
C15 C16 H16A 119.8 . .
C17 C16 H16A 119.8 . .
C16 C17 C18 120.1(3) . .
C16 C17 H17A 120.0 . .
C18 C17 H17A 120.0 . .
C13 C18 C17 120.1(3) . .
C13 C18 H18A 120.0 . .
C17 C18 H18A 120.0 . .
C20 C19 O5 121.0(2) . .
C20 C19 C7 128.9(2) . .
O5 C19 C7 110.1(2) . .
C19 C20 C27 123.8(2) . .
C19 C20 C21 119.0(2) . .
C27 C20 C21 117.1(2) . .
C20 C21 C1 116.0(2) . .
C20 C21 C22 105.65(19) . .
C1 C21 C22 110.8(2) . .
C20 C21 H21A 108.0 . .
C1 C21 H21A 108.0 . .
C22 C21 H21A 108.0 . .
C23 C22 C24 112.8(2) . .
C23 C22 C21 109.5(2) . .
C24 C22 C21 109.8(2) . .
C23 C22 H22A 108.2 . .
C24 C22 H22A 108.2 . .
C21 C22 H22A 108.2 . .
O4 C23 O5 117.5(2) . .
O4 C23 C22 126.5(2) . .
O5 C23 C22 116.0(2) . .
O1 C24 O2 125.7(3) . .
O1 C24 C22 123.2(3) . .
O2 C24 C22 111.1(2) . .
O2 C25 C26 106.8(3) . .
O2 C25 H25A 110.4 . .
C26 C25 H25A 110.4 . .
O2 C25 H25B 110.4 . .
C26 C25 H25B 110.4 . .
H25A C25 H25B 108.6 . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
O3 C27 C20 119.5(2) . .
O3 C27 C13 120.2(2) . .
C20 C27 C13 120.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.906(3) .
O1 C24 1.189(3) .
O2 C24 1.329(3) .
O2 C25 1.459(3) .
O3 C27 1.215(3) .
O4 C23 1.193(3) .
O5 C23 1.370(3) .
O5 C19 1.401(3) .
C1 C6 1.374(4) .
C1 C2 1.381(4) .
C1 C21 1.524(3) .
C2 C3 1.380(4) .
C2 H2A 0.9300 .
C3 C4 1.360(4) .
C3 H3A 0.9300 .
C4 C5 1.365(4) .
C5 C6 1.384(4) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 C8 1.382(4) .
C7 C12 1.386(4) .
C7 C19 1.475(3) .
C8 C9 1.380(4) .
C8 H8A 0.9300 .
C9 C10 1.368(5) .
C9 H9A 0.9300 .
C10 C11 1.372(5) .
C10 H10A 0.9300 .
C11 C12 1.380(4) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C13 C18 1.380(4) .
C13 C14 1.389(4) .
C13 C27 1.489(4) .
C14 C15 1.377(5) .
C14 H14A 0.9300 .
C15 C16 1.364(5) .
C15 H15A 0.9300 .
C16 C17 1.368(5) .
C16 H16A 0.9300 .
C17 C18 1.382(4) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 C20 1.331(3) .
C20 C27 1.487(3) .
C20 C21 1.521(3) .
C21 C22 1.540(3) .
C21 H21A 0.9800 .
C22 C23 1.501(4) .
C22 C24 1.523(4) .
C22 H22A 0.9800 .
C25 C26 1.462(5) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.7(5) . . . .
C21 C1 C2 C3 177.3(3) . . . .
C1 C2 C3 C4 0.3(5) . . . .
C2 C3 C4 C5 1.5(5) . . . .
C2 C3 C4 Br1 -179.9(2) . . . .
C3 C4 C5 C6 -1.7(5) . . . .
Br1 C4 C5 C6 179.7(2) . . . .
C2 C1 C6 C5 1.5(4) . . . .
C21 C1 C6 C5 -177.5(3) . . . .
C4 C5 C6 C1 0.1(5) . . . .
C12 C7 C8 C9 2.8(4) . . . .
C19 C7 C8 C9 -175.8(3) . . . .
C7 C8 C9 C10 -0.9(5) . . . .
C8 C9 C10 C11 -1.2(5) . . . .
C9 C10 C11 C12 1.4(5) . . . .
C10 C11 C12 C7 0.5(5) . . . .
C8 C7 C12 C11 -2.5(4) . . . .
C19 C7 C12 C11 176.0(3) . . . .
C18 C13 C14 C15 -2.5(4) . . . .
C27 C13 C14 C15 179.0(3) . . . .
C13 C14 C15 C16 2.9(5) . . . .
C14 C15 C16 C17 -0.8(5) . . . .
C15 C16 C17 C18 -1.6(5) . . . .
C14 C13 C18 C17 0.1(4) . . . .
C27 C13 C18 C17 178.6(3) . . . .
C16 C17 C18 C13 1.9(5) . . . .
C23 O5 C19 C20 23.0(3) . . . .
C23 O5 C19 C7 -158.9(2) . . . .
C8 C7 C19 C20 40.2(4) . . . .
C12 C7 C19 C20 -138.4(3) . . . .
C8 C7 C19 O5 -137.8(2) . . . .
C12 C7 C19 O5 43.6(3) . . . .
O5 C19 C20 C27 -179.2(2) . . . .
C7 C19 C20 C27 3.0(4) . . . .
O5 C19 C20 C21 -0.6(3) . . . .
C7 C19 C20 C21 -178.4(2) . . . .
C19 C20 C21 C1 84.1(3) . . . .
C27 C20 C21 C1 -97.2(3) . . . .
C19 C20 C21 C22 -39.0(3) . . . .
C27 C20 C21 C22 139.6(2) . . . .
C6 C1 C21 C20 -7.9(4) . . . .
C2 C1 C21 C20 173.1(3) . . . .
C6 C1 C21 C22 112.6(3) . . . .
C2 C1 C21 C22 -66.4(3) . . . .
C20 C21 C22 C23 57.9(2) . . . .
C1 C21 C22 C23 -68.5(2) . . . .
C20 C21 C22 C24 -66.5(3) . . . .
C1 C21 C22 C24 167.1(2) . . . .
C19 O5 C23 O4 -178.8(2) . . . .
C19 O5 C23 C22 0.4(3) . . . .
C24 C22 C23 O4 -99.8(3) . . . .
C21 C22 C23 O4 137.6(3) . . . .
C24 C22 C23 O5 81.1(3) . . . .
C21 C22 C23 O5 -41.5(3) . . . .
C25 O2 C24 O1 -6.0(4) . . . .
C25 O2 C24 C22 175.0(2) . . . .
C23 C22 C24 O1 -173.8(2) . . . .
C21 C22 C24 O1 -51.3(3) . . . .
C23 C22 C24 O2 5.2(3) . . . .
C21 C22 C24 O2 127.7(2) . . . .
C24 O2 C25 C26 166.3(3) . . . .
C19 C20 C27 O3 -138.8(3) . . . .
C21 C20 C27 O3 42.6(3) . . . .
C19 C20 C27 C13 44.6(4) . . . .
C21 C20 C27 C13 -134.0(2) . . . .
C18 C13 C27 O3 -143.5(3) . . . .
C14 C13 C27 O3 34.9(4) . . . .
C18 C13 C27 C20 33.0(4) . . . .
C14 C13 C27 C20 -148.5(3) . . . .
