# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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data_shelxl_A
_database_code_depnum_ccdc_archive 'CCDC 878989'
#TrackingRef 'RK A .cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-3-(4-(benzyloxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O3'
_chemical_formula_weight         330.36

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pca21

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

_cell_length_a                   11.814(3)
_cell_length_b                   18.304(5)
_cell_length_c                   7.957(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1720.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2418
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.90

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8699
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.11
_diffrn_reflns_theta_max         26.79
_reflns_number_total             3412
_reflns_number_gt                2474
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0930P)^2^+0.0665P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         3412
_refine_ls_number_parameters     228
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.134
_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
C1 C -0.5508(4) 0.3549(2) 0.2754(8) 0.0937(15) Uani 1 1 d U . .
H1 H -0.5649 0.3165 0.2017 0.112 Uiso 1 1 calc R . .
C2 C -0.6401(4) 0.3992(3) 0.3279(10) 0.1157(17) Uani 1 1 d U . .
H2 H -0.7131 0.3919 0.2875 0.139 Uiso 1 1 calc R . .
C3 C -0.6175(5) 0.4539(3) 0.4408(9) 0.1103(17) Uani 1 1 d U . .
H3 H -0.6760 0.4831 0.4810 0.132 Uiso 1 1 calc R . .
C4 C -0.5099(5) 0.4656(2) 0.4940(7) 0.0977(14) Uani 1 1 d U . .
H4 H -0.4942 0.5035 0.5684 0.117 Uiso 1 1 calc R . .
C5 C -0.4256(4) 0.4218(2) 0.4380(6) 0.0797(11) Uani 1 1 d U . .
H5 H -0.3523 0.4302 0.4760 0.096 Uiso 1 1 calc R . .
C6 C -0.4433(3) 0.3670(2) 0.3306(6) 0.0655(10) Uani 1 1 d U . .
C7 C -0.3518(3) 0.3157(2) 0.2694(5) 0.0689(10) Uani 1 1 d . . .
H7A H -0.3634 0.2674 0.3165 0.083 Uiso 1 1 calc R . .
H7B H -0.3547 0.3118 0.1479 0.083 Uiso 1 1 calc R . .
C8 C -0.1517(3) 0.30498(18) 0.2767(5) 0.0585(8) Uani 1 1 d . . .
C9 C -0.1490(2) 0.24076(18) 0.1879(4) 0.0529(8) Uani 1 1 d . . .
H9 H -0.2160 0.2189 0.1524 0.063 Uiso 1 1 calc R . .
C10 C -0.0457(2) 0.20881(17) 0.1516(4) 0.0505(7) Uani 1 1 d . . .
H10 H -0.0440 0.1656 0.0903 0.061 Uiso 1 1 calc R . .
C11 C 0.0554(2) 0.23967(16) 0.2045(4) 0.0471(7) Uani 1 1 d . . .
C12 C 0.0484(3) 0.3038(2) 0.2962(6) 0.0708(11) Uani 1 1 d . . .
H12 H 0.1148 0.3254 0.3348 0.085 Uiso 1 1 calc R . .
C13 C -0.0529(3) 0.3365(2) 0.3317(6) 0.0744(12) Uani 1 1 d . . .
H13 H -0.0549 0.3798 0.3927 0.089 Uiso 1 1 calc R . .
C14 C 0.1667(2) 0.20867(17) 0.1689(4) 0.0499(8) Uani 1 1 d . . .
H14 H 0.2277 0.2329 0.2172 0.060 Uiso 1 1 calc R . .
C15 C 0.1920(2) 0.15123(17) 0.0778(4) 0.0464(7) Uani 1 1 d . . .
H15 H 0.1343 0.1257 0.0242 0.056 Uiso 1 1 calc R . .
C16 C 0.3092(2) 0.12640(17) 0.0586(4) 0.0456(7) Uani 1 1 d . . .
C17 C 0.33249(19) 0.05714(16) -0.0289(3) 0.0406(6) Uani 1 1 d . . .
C18 C 0.2537(2) 0.00121(16) -0.0388(4) 0.0472(7) Uani 1 1 d . . .
H18 H 0.1825 0.0076 0.0089 0.057 Uiso 1 1 calc R . .
C19 C 0.2789(2) -0.06335(17) -0.1176(4) 0.0506(8) Uani 1 1 d . . .
H19 H 0.2256 -0.1007 -0.1203 0.061 Uiso 1 1 calc R . .
C20 C 0.3843(2) -0.07323(16) -0.1937(4) 0.0442(7) Uani 1 1 d . . .
C21 C 0.4638(2) -0.01771(16) -0.1847(4) 0.0440(7) Uani 1 1 d . . .
H21 H 0.5344 -0.0238 -0.2346 0.053 Uiso 1 1 calc R . .
C22 C 0.4389(2) 0.04587(17) -0.1029(4) 0.0447(7) Uani 1 1 d . . .
H22 H 0.4934 0.0824 -0.0961 0.054 Uiso 1 1 calc R . .
O1 O -0.2475(2) 0.34272(13) 0.3192(5) 0.0844(9) Uani 1 1 d . . .
O2 O 0.38842(16) 0.16241(13) 0.1167(3) 0.0598(6) Uani 1 1 d . . .
O3 O 0.40218(16) -0.13633(13) -0.2747(3) 0.0608(6) Uani 1 1 d . . .
H3A H 0.4669 -0.1370 -0.3118 0.091 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.084(3) 0.072(2) 0.125(4) -0.005(3) 0.011(2) -0.003(2)
C2 0.063(2) 0.121(3) 0.164(4) 0.014(4) 0.004(3) -0.007(2)
C3 0.098(3) 0.098(3) 0.135(4) 0.011(3) 0.038(3) 0.037(3)
C4 0.112(3) 0.073(2) 0.109(3) -0.004(3) 0.006(3) 0.017(3)
C5 0.068(2) 0.076(2) 0.096(3) 0.006(2) 0.0048(19) 0.0109(19)
C6 0.0538(18) 0.0618(19) 0.081(2) 0.014(2) 0.0124(17) 0.0109(16)
C7 0.070(2) 0.064(2) 0.073(2) -0.0019(19) 0.0042(18) 0.0050(18)
C8 0.0504(17) 0.0552(19) 0.070(2) -0.0003(18) 0.0141(15) 0.0127(15)
C9 0.0401(15) 0.0551(19) 0.064(2) 0.0015(17) -0.0003(13) 0.0054(13)
C10 0.0443(16) 0.0502(17) 0.0569(19) -0.0065(16) -0.0004(12) 0.0054(13)
C11 0.0450(15) 0.0464(16) 0.0499(18) -0.0008(15) 0.0068(13) 0.0037(13)
C12 0.0518(19) 0.065(2) 0.096(3) -0.023(2) 0.0073(18) -0.0063(16)
C13 0.061(2) 0.055(2) 0.107(3) -0.027(2) 0.020(2) -0.0060(16)
C14 0.0372(15) 0.0572(18) 0.0552(19) 0.0079(17) -0.0002(12) 0.0025(13)
C15 0.0352(14) 0.0543(17) 0.0498(17) 0.0010(16) 0.0008(12) 0.0082(12)
C16 0.0339(14) 0.0599(18) 0.0430(16) 0.0092(15) -0.0016(11) 0.0025(13)
C17 0.0307(12) 0.0519(17) 0.0391(14) 0.0059(14) -0.0013(11) 0.0039(11)
C18 0.0307(12) 0.0595(17) 0.0513(17) 0.0091(16) 0.0045(12) 0.0021(12)
C19 0.0317(13) 0.0564(18) 0.0639(19) 0.0080(17) 0.0037(13) -0.0049(13)
C20 0.0321(13) 0.0513(17) 0.0492(16) 0.0056(16) 0.0003(12) 0.0021(11)
C21 0.0292(12) 0.0609(18) 0.0419(15) 0.0032(15) 0.0017(11) 0.0029(11)
C22 0.0319(12) 0.0570(18) 0.0453(16) 0.0066(15) 0.0006(11) -0.0018(13)
O1 0.0541(14) 0.0780(16) 0.121(2) -0.0160(19) 0.0173(14) 0.0101(13)
O2 0.0401(12) 0.0582(13) 0.0811(17) -0.0062(13) -0.0044(10) 0.0042(10)
O3 0.0403(12) 0.0563(13) 0.0857(17) -0.0092(13) 0.0111(11) -0.0036(10)

_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
C1 C6 1.362(6) . ?
C1 C2 1.395(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.334(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(5) . ?
C7 O1 1.386(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.368(4) . ?
C8 C9 1.372(5) . ?
C8 C13 1.373(5) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(5) . ?
C11 C14 1.460(4) . ?
C12 C13 1.368(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.311(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.466(4) . ?
C15 H15 0.9300 . ?
C16 O2 1.234(4) . ?
C16 C17 1.472(4) . ?
C17 C18 1.386(4) . ?
C17 C22 1.403(4) . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(4) . ?
C19 H19 0.9300 . ?
C20 O3 1.339(4) . ?
C20 C21 1.385(4) . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
O3 H3A 0.8200 . ?

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
C6 C1 C2 120.9(5) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 122.8(4) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 C7 124.1(4) . . ?
C1 C6 C7 117.5(4) . . ?
O1 C7 C6 108.8(3) . . ?
O1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C8 C9 125.3(3) . . ?
O1 C8 C13 114.3(3) . . ?
C9 C8 C13 120.3(3) . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 117.0(3) . . ?
C12 C11 C14 119.0(3) . . ?
C10 C11 C14 123.9(3) . . ?
C13 C12 C11 122.1(3) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C15 C14 C11 128.6(3) . . ?
C15 C14 H14 115.7 . . ?
C11 C14 H14 115.7 . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
O2 C16 C15 120.8(3) . . ?
O2 C16 C17 119.7(2) . . ?
C15 C16 C17 119.5(2) . . ?
C18 C17 C22 118.0(3) . . ?
C18 C17 C16 122.5(2) . . ?
C22 C17 C16 119.5(2) . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
O3 C20 C21 123.4(2) . . ?
O3 C20 C19 117.4(3) . . ?
C21 C20 C19 119.1(3) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 121.2(3) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C8 O1 C7 119.0(3) . . ?
C20 O3 H3A 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 -2.1(8) . . . . ?
C1 C2 C3 C4 2.4(9) . . . . ?
C2 C3 C4 C5 -1.6(9) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 0.0(7) . . . . ?
C4 C5 C6 C7 -178.2(4) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
C2 C1 C6 C7 179.1(5) . . . . ?
C5 C6 C7 O1 -10.2(6) . . . . ?
C1 C6 C7 O1 171.6(4) . . . . ?
O1 C8 C9 C10 179.2(3) . . . . ?
C13 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C9 C10 C11 C14 -179.5(3) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C14 C11 C12 C13 178.9(4) . . . . ?
C11 C12 C13 C8 0.6(7) . . . . ?
O1 C8 C13 C12 -179.8(4) . . . . ?
C9 C8 C13 C12 0.5(6) . . . . ?
C12 C11 C14 C15 -176.0(4) . . . . ?
C10 C11 C14 C15 3.8(5) . . . . ?
C11 C14 C15 C16 -178.4(3) . . . . ?
C14 C15 C16 O2 -5.9(4) . . . . ?
C14 C15 C16 C17 173.2(3) . . . . ?
O2 C16 C17 C18 154.1(3) . . . . ?
C15 C16 C17 C18 -25.1(4) . . . . ?
O2 C16 C17 C22 -24.6(4) . . . . ?
C15 C16 C17 C22 156.2(3) . . . . ?
C22 C17 C18 C19 0.3(4) . . . . ?
C16 C17 C18 C19 -178.4(3) . . . . ?
C17 C18 C19 C20 -1.7(5) . . . . ?
C18 C19 C20 O3 -177.3(3) . . . . ?
C18 C19 C20 C21 1.6(4) . . . . ?
O3 C20 C21 C22 178.6(3) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 -1.1(4) . . . . ?
C18 C17 C22 C21 1.1(4) . . . . ?
C16 C17 C22 C21 179.8(3) . . . . ?
C9 C8 O1 C7 -0.5(6) . . . . ?
C13 C8 O1 C7 179.9(4) . . . . ?
C6 C7 O1 C8 -179.7(3) . . . . ?

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
O3 H3A O2 0.82 1.86 2.664(3) 166.1 2_654

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.79
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.061




data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 878990'
#TrackingRef 'ram2.cif'


_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(E)-1-(4-(benzyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C22 H18 O3'
_chemical_formula_weight 330.36

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'

_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 18.9810(6)
_cell_length_b 7.5355(3)
_cell_length_c 24.6569(7)
_cell_angle_alpha 90.00
_cell_angle_beta 105.108(2)
_cell_angle_gamma 90.00
_cell_volume 3404.8(2)
_cell_formula_units_Z 8
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 5143
_cell_measurement_theta_min 2.923
_cell_measurement_theta_max 26.065

_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.289
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1392
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9645
_exptl_absorpt_correction_T_max 0.9986
_exptl_absorpt_process_details 'SADABS (Bruker, 1999)'

_exptl_special_details
;
?
;

_diffrn_ambient_temperature 293(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method '\w and \f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17130
_diffrn_reflns_av_R_equivalents 0.0300
_diffrn_reflns_av_sigmaI/netI 0.0235
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 2.22
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2989
_reflns_number_gt 2259
_reflns_threshold_expression >2sigma(I)

_computing_data_collection 'APEX2 (Bruker, 2004)'
_computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction 'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution 'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 2008)'


_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0710P)^2^+0.5566P] where P=(Fo^2^+2Fc^2^)/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 2989
_refine_ls_number_parameters 226
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0537
_refine_ls_R_factor_gt 0.0370
_refine_ls_wR_factor_ref 0.1209
_refine_ls_wR_factor_gt 0.1060
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_restrained_S_all 1.029
_refine_ls_shift/su_max 0.003
_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
C1 C 0.85127(10) -0.0937(2) 0.13947(7) 0.0589(5) Uani 1 1 d . . .
H1 H 0.8123 -0.1585 0.1455 0.071 Uiso 1 1 calc R . .
C2 C 0.91651(11) -0.0872(2) 0.18050(7) 0.0703(5) Uani 1 1 d . . .
H2 H 0.9213 -0.1492 0.2139 0.084 Uiso 1 1 calc R . .
C3 C 0.97434(10) 0.0093(2) 0.17272(7) 0.0641(5) Uani 1 1 d . . .
H3 H 1.0179 0.0140 0.2008 0.077 Uiso 1 1 calc R . .
C4 C 0.96739(9) 0.0988(2) 0.12326(7) 0.0578(4) Uani 1 1 d . . .
H4 H 1.0064 0.1644 0.1176 0.069 Uiso 1 1 calc R . .
C5 C 0.90274(8) 0.0917(2) 0.08192(6) 0.0506(4) Uani 1 1 d . . .
H5 H 0.8986 0.1524 0.0484 0.061 Uiso 1 1 calc R . .
C6 C 0.84403(8) -0.00362(19) 0.08939(6) 0.0427(4) Uani 1 1 d . . .
C7 C 0.77531(8) -0.00356(19) 0.04304(6) 0.0461(4) Uani 1 1 d . . .
H7A H 0.7564 0.1164 0.0367 0.055 Uiso 1 1 calc R . .
H7B H 0.7854 -0.0455 0.0086 0.055 Uiso 1 1 calc R . .
C8 C 0.65612(8) -0.12923(19) 0.01967(6) 0.0434(4) Uani 1 1 d . . .
C9 C 0.63749(8) -0.0478(2) -0.03209(6) 0.0501(4) Uani 1 1 d . . .
H9 H 0.6712 0.0225 -0.0436 0.060 Uiso 1 1 calc R . .
C10 C 0.56828(9) -0.0718(2) -0.06665(6) 0.0501(4) Uani 1 1 d . . .
H10 H 0.5559 -0.0162 -0.1015 0.060 Uiso 1 1 calc R . .
C11 C 0.51683(8) -0.17542(18) -0.05120(5) 0.0408(3) Uani 1 1 d . . .
C12 C 0.53741(8) -0.2580(2) 0.00113(6) 0.0488(4) Uani 1 1 d . . .
H12 H 0.5041 -0.3297 0.0125 0.059 Uiso 1 1 calc R . .
C13 C 0.60568(8) -0.2356(2) 0.03592(6) 0.0515(4) Uani 1 1 d . . .
H13 H 0.6184 -0.2920 0.0707 0.062 Uiso 1 1 calc R . .
C14 C 0.44182(8) -0.19939(19) -0.08675(6) 0.0453(4) Uani 1 1 d . . .
C15 C 0.42146(8) -0.1248(2) -0.14386(6) 0.0498(4) Uani 1 1 d . . .
H15 H 0.4584 -0.0968 -0.1609 0.060 Uiso 1 1 calc R . .
C16 C 0.35322(9) -0.0961(2) -0.17200(6) 0.0494(4) Uani 1 1 d . . .
H16 H 0.3182 -0.1182 -0.1526 0.059 Uiso 1 1 calc R . .
C17 C 0.32552(8) -0.03379(19) -0.22986(6) 0.0454(4) Uani 1 1 d . . .
C18 C 0.36987(8) 0.0394(2) -0.26108(6) 0.0514(4) Uani 1 1 d . . .
H18 H 0.4195 0.0538 -0.2444 0.062 Uiso 1 1 calc R . .
C19 C 0.34192(8) 0.0909(2) -0.31590(6) 0.0523(4) Uani 1 1 d . . .
H19 H 0.3724 0.1405 -0.3358 0.063 Uiso 1 1 calc R . .
C20 C 0.26834(8) 0.06890(19) -0.34155(6) 0.0460(4) Uani 1 1 d . . .
C21 C 0.22336(8) -0.0031(2) -0.31151(6) 0.0506(4) Uani 1 1 d . . .
H21 H 0.1739 -0.0190 -0.3285 0.061 Uiso 1 1 calc R . .
C22 C 0.25182(9) -0.0515(2) -0.25631(7) 0.0516(4) Uani 1 1 d . . .
H22 H 0.2208 -0.0972 -0.2362 0.062 Uiso 1 1 calc R . .
O1 O 0.72257(5) -0.11499(15) 0.05723(4) 0.0549(3) Uani 1 1 d . . .
O2 O 0.39718(6) -0.28317(16) -0.06850(4) 0.0601(3) Uani 1 1 d . . .
O3 O 0.24356(6) 0.12166(16) -0.39591(4) 0.0603(3) Uani 1 1 d . . .
H3A H 0.2008 0.1525 -0.4019 0.090 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0622(11) 0.0628(10) 0.0468(9) 0.0040(8) 0.0052(8) -0.0168(8)
C2 0.0806(13) 0.0763(12) 0.0427(10) 0.0107(8) -0.0041(9) -0.0133(10)
C3 0.0539(10) 0.0777(12) 0.0500(10) -0.0017(9) -0.0053(8) -0.0016(9)
C4 0.0446(9) 0.0726(11) 0.0546(10) -0.0017(8) 0.0103(8) -0.0044(8)
C5 0.0477(9) 0.0605(10) 0.0431(8) 0.0040(7) 0.0109(7) 0.0017(8)
C6 0.0460(9) 0.0417(8) 0.0389(8) -0.0045(6) 0.0083(6) 0.0004(7)
C7 0.0463(9) 0.0470(9) 0.0424(8) 0.0004(7) 0.0068(7) -0.0029(7)
C8 0.0411(8) 0.0472(8) 0.0387(8) -0.0002(6) 0.0048(6) 0.0005(7)
C9 0.0470(9) 0.0549(9) 0.0456(9) 0.0087(7) 0.0074(7) -0.0083(7)
C10 0.0532(10) 0.0549(10) 0.0384(8) 0.0110(7) 0.0049(7) -0.0040(8)
C11 0.0430(8) 0.0412(8) 0.0367(8) -0.0009(6) 0.0079(6) 0.0007(6)
C12 0.0469(9) 0.0571(9) 0.0421(8) 0.0056(7) 0.0110(7) -0.0085(7)
C13 0.0485(9) 0.0664(10) 0.0372(8) 0.0127(7) 0.0068(7) -0.0038(8)
C14 0.0472(9) 0.0465(8) 0.0402(8) -0.0017(6) 0.0076(7) -0.0019(7)
C15 0.0463(9) 0.0604(10) 0.0393(8) 0.0031(7) 0.0053(7) -0.0019(7)
C16 0.0492(10) 0.0509(9) 0.0466(9) 0.0057(7) 0.0099(7) -0.0024(7)
C17 0.0432(9) 0.0474(9) 0.0432(8) 0.0038(6) 0.0072(7) 0.0011(7)
C18 0.0388(9) 0.0628(10) 0.0503(9) 0.0059(7) 0.0074(7) 0.0027(7)
C19 0.0456(9) 0.0668(10) 0.0483(9) 0.0072(7) 0.0186(7) 0.0048(8)
C20 0.0497(9) 0.0506(9) 0.0375(8) 0.0012(6) 0.0109(7) 0.0099(7)
C21 0.0403(9) 0.0586(10) 0.0488(9) 0.0053(7) 0.0045(7) -0.0003(7)
C22 0.0455(9) 0.0583(10) 0.0504(9) 0.0097(7) 0.0113(7) -0.0024(7)
O1 0.0441(6) 0.0691(7) 0.0458(6) 0.0122(5) 0.0014(5) -0.0097(5)
O2 0.0491(7) 0.0760(8) 0.0498(6) 0.0100(5) 0.0031(5) -0.0141(6)
O3 0.0562(7) 0.0844(8) 0.0401(6) 0.0105(5) 0.0124(5) 0.0167(6)

_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
C1 C2 1.381(2) . ?
C1 C6 1.384(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(2) . ?
C7 O1 1.4186(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.3606(17) . ?
C8 C9 1.377(2) . ?
C8 C13 1.386(2) . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.3936(19) . ?
C11 C14 1.4757(19) . ?
C12 C13 1.365(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O2 1.2320(17) . ?
C14 C15 1.471(2) . ?
C15 C16 1.318(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.463(2) . ?
C16 H16 0.9300 . ?
C17 C22 1.387(2) . ?
C17 C18 1.394(2) . ?
C18 C19 1.373(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9300 . ?
C20 O3 1.3591(17) . ?
C20 C21 1.379(2) . ?
C21 C22 1.376(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
O3 H3A 0.8200 . ?

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
C2 C1 C6 119.85(16) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.93(16) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.41(15) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.04(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.12(15) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.64(14) . . ?
C5 C6 C7 118.23(13) . . ?
C1 C6 C7 123.12(14) . . ?
O1 C7 C6 110.05(11) . . ?
O1 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
O1 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O1 C8 C9 124.37(13) . . ?
O1 C8 C13 115.88(12) . . ?
C9 C8 C13 119.75(13) . . ?
C8 C9 C10 119.19(14) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 122.18(14) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 117.44(13) . . ?
C10 C11 C14 123.24(13) . . ?
C12 C11 C14 119.31(13) . . ?
C13 C12 C11 121.17(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C8 120.26(13) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
O2 C14 C15 120.75(13) . . ?
O2 C14 C11 119.64(13) . . ?
C15 C14 C11 119.60(13) . . ?
C16 C15 C14 122.93(15) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C17 128.32(15) . . ?
C15 C16 H16 115.8 . . ?
C17 C16 H16 115.8 . . ?
C22 C17 C18 117.28(13) . . ?
C22 C17 C16 119.32(14) . . ?
C18 C17 C16 123.38(13) . . ?
C19 C18 C17 121.43(14) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 120.06(15) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
O3 C20 C21 122.77(14) . . ?
O3 C20 C19 117.66(14) . . ?
C21 C20 C19 119.57(13) . . ?
C22 C21 C20 119.80(14) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C17 121.83(15) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
C8 O1 C7 117.85(11) . . ?
C20 O3 H3A 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 0.8(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 179.24(14) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 -179.82(15) . . . . ?
C5 C6 C7 O1 177.24(13) . . . . ?
C1 C6 C7 O1 -3.2(2) . . . . ?
O1 C8 C9 C10 -179.90(14) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C14 178.33(14) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C14 C11 C12 C13 -178.31(14) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
O1 C8 C13 C12 179.90(14) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C10 C11 C14 O2 -174.63(14) . . . . ?
C12 C11 C14 O2 4.2(2) . . . . ?
C10 C11 C14 C15 6.1(2) . . . . ?
C12 C11 C14 C15 -175.00(13) . . . . ?
O2 C14 C15 C16 20.4(2) . . . . ?
C11 C14 C15 C16 -160.41(15) . . . . ?
C14 C15 C16 C17 -175.73(14) . . . . ?
C15 C16 C17 C22 164.81(16) . . . . ?
C15 C16 C17 C18 -13.5(3) . . . . ?
C22 C17 C18 C19 -0.5(2) . . . . ?
C16 C17 C18 C19 177.84(15) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 O3 -179.85(14) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
O3 C20 C21 C22 -179.06(14) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C20 C21 C22 C17 -1.5(2) . . . . ?
C18 C17 C22 C21 1.5(2) . . . . ?
C16 C17 C22 C21 -176.82(14) . . . . ?
C9 C8 O1 C7 2.5(2) . . . . ?
C13 C8 O1 C7 -178.33(13) . . . . ?
C6 C7 O1 C8 179.46(12) . . . . ?

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
O3 H3A O2 0.82 1.88 2.6830(15) 168.0 4_554

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.138
_refine_diff_density_min -0.153
_refine_diff_density_rms 0.031