# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_chenc-28
_database_code_depnum_ccdc_archive 'CCDC 1019497'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
6-(4-bromophenyl)-5-phenyl-3,4-dihydro-2H-pyran
_chemical_name_common            ?
_chemical_melting_point          92.8-94.1
_chemical_formula_moiety         'C17 H15 Br O'
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20

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)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   5.7276(19)
_cell_length_b                   18.038(7)
_cell_length_c                   13.687(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.05(3)
_cell_angle_gamma                90.00
_cell_volume                     1392.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    42
_cell_measurement_theta_min      5.59
_cell_measurement_theta_max      12.65

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    2.941
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1671
_exptl_absorpt_correction_T_max  0.3721
_exptl_absorpt_process_details   'North, et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3563
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2542
_reflns_number_gt                1682
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_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)+(0.0010P)²+2.5000P] 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         2542
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.250
_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
Br1 Br 1.24098(12) 0.61982(4) 0.45250(5) 0.0631(3) Uani 1 1 d . . .
O1 O 0.7875(8) 0.7083(2) 0.8558(3) 0.0632(12) Uani 1 1 d . . .
C1 C 1.0914(9) 0.6239(4) 0.5655(4) 0.0457(13) Uani 1 1 d . . .
C2 C 1.1790(11) 0.6698(4) 0.6412(5) 0.0567(17) Uani 1 1 d . . .
H2 H 1.3138 0.6979 0.6385 0.068 Uiso 1 1 calc R . .
C3 C 1.0660(10) 0.6746(4) 0.7235(5) 0.0520(16) Uani 1 1 d . . .
H3 H 1.1240 0.7066 0.7753 0.062 Uiso 1 1 calc R . .
C4 C 0.8688(10) 0.6321(3) 0.7277(4) 0.0448(14) Uani 1 1 d . . .
C5 C 0.7813(10) 0.5871(4) 0.6497(4) 0.0476(15) Uani 1 1 d . . .
H5 H 0.6455 0.5591 0.6513 0.057 Uiso 1 1 calc R . .
C6 C 0.8955(10) 0.5828(3) 0.5672(4) 0.0468(14) Uani 1 1 d . . .
H6 H 0.8368 0.5519 0.5142 0.056 Uiso 1 1 calc R . .
C7 C 0.7543(11) 0.6388(3) 0.8174(4) 0.0475(15) Uani 1 1 d . . .
C8 C 0.6331(11) 0.5862(4) 0.8561(4) 0.0490(15) Uani 1 1 d . . .
C9 C 0.5152(14) 0.6039(4) 0.9457(5) 0.069(2) Uani 1 1 d . . .
H9A H 0.3507 0.5884 0.9313 0.083 Uiso 1 1 calc R . .
H9B H 0.5931 0.5757 1.0024 0.083 Uiso 1 1 calc R . .
C10 C 0.5253(15) 0.6849(4) 0.9718(5) 0.074(2) Uani 1 1 d . . .
H10A H 0.3968 0.7110 0.9302 0.089 Uiso 1 1 calc R . .
H10B H 0.5066 0.6911 1.0404 0.089 Uiso 1 1 calc R . .
C11 C 0.7543(14) 0.7164(5) 0.9573(5) 0.076(2) Uani 1 1 d . . .
H11A H 0.7600 0.7685 0.9749 0.091 Uiso 1 1 calc R . .
H11B H 0.8820 0.6914 1.0008 0.091 Uiso 1 1 calc R . .
C12 C 0.6107(10) 0.5091(4) 0.8216(4) 0.0459(14) Uani 1 1 d . . .
C13 C 0.7979(11) 0.4599(4) 0.8418(5) 0.0563(17) Uani 1 1 d . . .
H13 H 0.9440 0.4763 0.8755 0.068 Uiso 1 1 calc R . .
C14 C 0.7697(13) 0.3863(4) 0.8123(5) 0.0623(18) Uani 1 1 d . . .
H14 H 0.8973 0.3539 0.8263 0.075 Uiso 1 1 calc R . .
C15 C 0.5575(13) 0.3611(4) 0.7631(5) 0.0612(18) Uani 1 1 d . . .
H15 H 0.5392 0.3118 0.7433 0.073 Uiso 1 1 calc R . .
C16 C 0.3721(12) 0.4094(4) 0.7433(5) 0.0634(19) Uani 1 1 d . . .
H16 H 0.2268 0.3929 0.7090 0.076 Uiso 1 1 calc R . .
C17 C 0.3975(11) 0.4822(4) 0.7736(5) 0.0550(16) Uani 1 1 d . . .
H17 H 0.2673 0.5138 0.7612 0.066 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
Br1 C1 1.895(5) . ?
O1 C7 1.360(7) . ?
O1 C11 1.443(8) . ?
C1 C6 1.348(8) . ?
C1 C2 1.353(9) . ?
C2 C3 1.396(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(8) . ?
C4 C7 1.494(8) . ?
C5 C6 1.403(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.339(8) . ?
C8 C12 1.467(9) . ?
C8 C9 1.533(8) . ?
C9 C10 1.503(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.474(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.370(8) . ?
C12 C13 1.382(9) . ?
C13 C14 1.389(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(10) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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 O1 C11 115.6(5) . . ?
C6 C1 C2 121.4(5) . . ?
C6 C1 Br1 119.3(4) . . ?
C2 C1 Br1 119.3(4) . . ?
C1 C2 C3 119.6(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 C7 122.5(5) . . ?
C3 C4 C7 118.1(5) . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.4(6) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 O1 123.2(5) . . ?
C8 C7 C4 126.8(6) . . ?
O1 C7 C4 110.0(5) . . ?
C7 C8 C12 124.5(5) . . ?
C7 C8 C9 120.0(6) . . ?
C12 C8 C9 115.4(5) . . ?
C10 C9 C8 112.9(6) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 109.9(6) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 C10 111.1(6) . . ?
O1 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C17 C12 C13 117.6(6) . . ?
C17 C12 C8 120.7(6) . . ?
C13 C12 C8 121.5(6) . . ?
C12 C13 C14 120.6(6) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.8(7) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.8(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 120.8(7) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 121.3(6) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.105
