# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1042880'
_audit_update_record             
;
2015-01-10 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'ethyl 5-benzoyl-4-(4-bromophenyl)-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 Br O5'
_chemical_formula_weight         505.35

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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'

_cell_length_a                   8.0879(3)
_cell_length_b                   27.2026(11)
_cell_length_c                   10.7134(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3740(10)
_cell_angle_gamma                90.00
_cell_volume                     2352.99(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_T_max  0.7515
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27224
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4160
_reflns_number_gt                3221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0356P)²+1.8737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4160
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
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_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
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_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
_geom_torsion_publ_flag
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) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1043017'
_audit_update_record             
;
2015-01-10 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(6-fluoro-2-methyl-5-(phenylethynyl)-4H-pyran-3-yl)ethanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F O2'
_chemical_formula_weight         256.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.8977(9)
_cell_length_b                   8.7711(3)
_cell_length_c                   11.9279(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.1810(10)
_cell_angle_gamma                90.00
_cell_volume                     2526.40(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14325
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2229
_reflns_number_gt                1924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+1.8099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2229
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.02869(3) 0.13666(11) 0.64767(8) 0.0414(3) Uani 1 1 d . . .
O1 O -0.05717(4) 0.06582(11) 0.57481(9) 0.0309(3) Uani 1 1 d . . .
O2 O -0.20404(5) 0.00788(14) 0.27035(10) 0.0466(3) Uani 1 1 d . . .
C1 C 0.15383(6) 0.48356(16) 0.50889(13) 0.0286(3) Uani 1 1 d . . .
H1A H 0.1613 0.4228 0.5789 0.034 Uiso 1 1 calc R . .
C2 C 0.19603(6) 0.56565(16) 0.49233(14) 0.0318(3) Uani 1 1 d . . .
H2A H 0.2324 0.5608 0.5510 0.038 Uiso 1 1 calc R . .
C3 C 0.18568(6) 0.65483(16) 0.39100(14) 0.0332(3) Uani 1 1 d . . .
H3A H 0.2150 0.7101 0.3796 0.040 Uiso 1 1 calc R . .
C4 C 0.13250(6) 0.66352(16) 0.30608(14) 0.0322(3) Uani 1 1 d . . .
H4A H 0.1252 0.7263 0.2372 0.039 Uiso 1 1 calc R . .
C5 C 0.09000(6) 0.58096(16) 0.32146(13) 0.0303(3) Uani 1 1 d . . .
H5A H 0.0537 0.5866 0.2626 0.036 Uiso 1 1 calc R . .
C6 C 0.10015(5) 0.48941(15) 0.42296(13) 0.0271(3) Uani 1 1 d . . .
C7 C 0.05654(6) 0.40099(16) 0.43806(13) 0.0303(3) Uani 1 1 d . . .
C8 C 0.02067(6) 0.32446(16) 0.45113(13) 0.0303(3) Uani 1 1 d . . .
C9 C -0.02427(5) 0.23817(15) 0.45991(13) 0.0277(3) Uani 1 1 d . . .
C10 C -0.08006(6) 0.24579(17) 0.35948(13) 0.0299(3) Uani 1 1 d . . .
H10A H -0.0759 0.2190 0.2826 0.036 Uiso 1 1 calc R . .
H10B H -0.0944 0.3513 0.3526 0.036 Uiso 1 1 calc R . .
C11 C -0.12109(5) 0.13805(15) 0.38155(12) 0.0248(3) Uani 1 1 d . . .
C12 C -0.10910(5) 0.05886(15) 0.48347(12) 0.0251(3) Uani 1 1 d . . .
C13 C -0.01848(5) 0.15180(16) 0.55431(13) 0.0286(3) Uani 1 1 d . . .
C14 C -0.17708(6) 0.12491(16) 0.28614(13) 0.0287(3) Uani 1 1 d . . .
C15 C -0.19940(6) 0.26132(18) 0.20785(14) 0.0351(4) Uani 1 1 d . . .
H15A H -0.2362 0.2377 0.1491 0.053 Uiso 1 1 calc R . .
H15B H -0.1745 0.2878 0.1655 0.053 Uiso 1 1 calc R . .
H15C H -0.2020 0.3475 0.2578 0.053 Uiso 1 1 calc R . .
C16 C -0.14462(6) -0.04188(17) 0.52500(14) 0.0344(4) Uani 1 1 d . . .
H16A H -0.1815 -0.0489 0.4622 0.052 Uiso 1 1 calc R . .
H16B H -0.1477 0.0004 0.5983 0.052 Uiso 1 1 calc R . .
H16C H -0.1280 -0.1437 0.5419 0.052 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
F1 C13 1.3294(16) . ?
O1 C13 1.3451(17) . ?
O1 C12 1.3930(17) . ?
O2 C14 1.2172(17) . ?
C1 C2 1.3813(19) . ?
C1 C6 1.3986(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.382(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4339(19) . ?
C7 C8 1.201(2) . ?
C8 C9 1.4234(19) . ?
C9 C13 1.320(2) . ?
C9 C10 1.5087(19) . ?
C10 C11 1.5145(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3357(19) . ?
C11 C14 1.4895(19) . ?
C12 C16 1.4836(19) . ?
C14 C15 1.499(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C13 O1 C12 117.03(11) . . ?
C2 C1 C6 120.29(13) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C1 C2 C3 120.44(13) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 C4 119.85(13) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 120.15(14) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.41(13) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 118.84(12) . . ?
C5 C6 C7 120.66(13) . . ?
C1 C6 C7 120.49(13) . . ?
C8 C7 C6 178.73(15) . . ?
C7 C8 C9 176.35(16) . . ?
C13 C9 C8 121.61(13) . . ?
C13 C9 C10 118.93(12) . . ?
C8 C9 C10 119.46(13) . . ?
C9 C10 C11 111.42(12) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C14 119.81(12) . . ?
C12 C11 C10 122.39(12) . . ?
C14 C11 C10 117.78(12) . . ?
C11 C12 O1 122.02(12) . . ?
C11 C12 C16 130.19(13) . . ?
O1 C12 C16 107.75(11) . . ?
C9 C13 F1 123.95(12) . . ?
C9 C13 O1 127.91(13) . . ?
F1 C13 O1 108.13(12) . . ?
O2 C14 C11 121.94(13) . . ?
O2 C14 C15 120.41(13) . . ?
C11 C14 C15 117.64(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -178.60(13) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C6 C7 178.20(13) . . . . ?
C5 C6 C7 C8 129(7) . . . . ?
C1 C6 C7 C8 -50(7) . . . . ?
C6 C7 C8 C9 -134(6) . . . . ?
C7 C8 C9 C13 -173(2) . . . . ?
C7 C8 C9 C10 7(2) . . . . ?
C13 C9 C10 C11 -4.30(18) . . . . ?
C8 C9 C10 C11 176.02(12) . . . . ?
C9 C10 C11 C12 5.62(19) . . . . ?
C9 C10 C11 C14 -176.01(11) . . . . ?
C14 C11 C12 O1 179.23(11) . . . . ?
C10 C11 C12 O1 -2.4(2) . . . . ?
C14 C11 C12 C16 -3.5(2) . . . . ?
C10 C11 C12 C16 174.88(14) . . . . ?
C13 O1 C12 C11 -2.47(18) . . . . ?
C13 O1 C12 C16 179.69(11) . . . . ?
C8 C9 C13 F1 -0.4(2) . . . . ?
C10 C9 C13 F1 179.96(12) . . . . ?
C8 C9 C13 O1 179.45(13) . . . . ?
C10 C9 C13 O1 -0.2(2) . . . . ?
C12 O1 C13 C9 3.9(2) . . . . ?
C12 O1 C13 F1 -176.22(10) . . . . ?
C12 C11 C14 O2 -31.3(2) . . . . ?
C10 C11 C14 O2 150.28(14) . . . . ?
C12 C11 C14 C15 149.43(13) . . . . ?
C10 C11 C14 C15 -28.99(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
