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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_added_by_encifer

_chemical_name_common            
;
3-(benzo[d][1,3]dioxol-2-yl)-1-phenyl-2-(pyridin-3-yl)propan-1-one
;
_chemical_formula_moiety         .
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_exptl_crystal_colour            colorless
_chemical_melting_point          149-150
_exptl_crystal_description       block
_exptl_crystal_preparation       'ethyl acetate'
_cell_length_a                   10.2758(3)
_cell_length_b                   8.60590(15)
_cell_length_c                   10.5383(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.016(4)
_cell_angle_gamma                90.00

_cell_volume                     822.72(4)
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2yb'

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

_cell_formula_units_Z            2
_exptl_crystal_density_diffrn    1.338

_diffrn_ambient_temperature      223(2)
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1061

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
O2 O 0.68834(16) 0.2888(2) 0.59085(14) 0.0448(4) Uani 1 1 d . . .
O1 O 0.96533(18) 0.5843(2) 0.39588(16) 0.0540(5) Uani 1 1 d . . .
O3 O 0.50989(17) 0.3907(2) 0.37678(15) 0.0470(4) Uani 1 1 d . . .
C8 C 0.7453(2) 0.4322(2) 0.28136(18) 0.0316(4) Uani 1 1 d . . .
H8 H 0.6489 0.4803 0.2227 0.038 Uiso 1 1 calc R . .
C7 C 0.8648(2) 0.5403(2) 0.2827(2) 0.0337(4) Uani 1 1 d . . .
N1 N 0.61710(19) 0.0827(2) 0.03434(18) 0.0402(4) Uani 1 1 d . . .
C21 C 0.5584(2) 0.3061(3) 0.5972(2) 0.0363(4) Uani 1 1 d . . .
C9 C 0.6229(2) 0.2167(2) 0.1001(2) 0.0346(4) Uani 1 1 d . . .
H9 H 0.5362 0.2739 0.0674 0.042 Uiso 1 1 calc R . .
C1 C 0.9827(2) 0.6612(3) 0.1480(2) 0.0393(5) Uani 1 1 d . . .
H1 H 1.0657 0.6779 0.2360 0.047 Uiso 1 1 calc R . .
C11 C 0.8770(2) 0.1887(3) 0.2648(2) 0.0365(4) Uani 1 1 d . . .
H11 H 0.9637 0.2228 0.3424 0.044 Uiso 1 1 calc R . .
C5 C 0.7349(2) 0.5647(2) 0.0106(2) 0.0348(4) Uani 1 1 d . . .
H5 H 0.6517 0.5166 0.0057 0.042 Uiso 1 1 calc R . .
C6 C 0.8592(2) 0.5870(2) 0.14362(19) 0.0309(4) Uani 1 1 d . . .
C17 C 0.3149(3) 0.4077(3) 0.4519(3) 0.0480(5) Uani 1 1 d . . .
H17 H 0.2435 0.4511 0.3666 0.058 Uiso 1 1 calc R . .
C13 C 0.7434(2) 0.0018(2) 0.0830(2) 0.0404(5) Uani 1 1 d . . .
H13 H 0.7432 -0.0905 0.0370 0.048 Uiso 1 1 calc R . .
C20 C 0.5330(3) 0.2757(3) 0.7109(2) 0.0434(5) Uani 1 1 d . . .
H20 H 0.6050 0.2323 0.7957 0.052 Uiso 1 1 calc R . .
C15 C 0.6513(2) 0.3140(3) 0.4424(2) 0.0381(4) Uani 1 1 d . . .
H15 H 0.6443 0.2141 0.3949 0.046 Uiso 1 1 calc R . .
C18 C 0.2876(3) 0.3786(3) 0.5678(3) 0.0518(6) Uani 1 1 d . . .
H18 H 0.1961 0.4040 0.5600 0.062 Uiso 1 1 calc R . .
C12 C 0.8736(2) 0.0497(3) 0.1985(2) 0.0409(5) Uani 1 1 d . . .
H12 H 0.9580 -0.0113 0.2311 0.049 Uiso 1 1 calc R . .
C19 C 0.3937(3) 0.3131(3) 0.6934(3) 0.0504(6) Uani 1 1 d . . .
H19 H 0.3716 0.2934 0.7680 0.061 Uiso 1 1 calc R . .
C10 C 0.7492(2) 0.2773(2) 0.21424(18) 0.0298(4) Uani 1 1 d . . .
C4 C 0.7358(2) 0.6142(3) -0.1140(2) 0.0417(5) Uani 1 1 d . . .
H4 H 0.6529 0.5985 -0.2023 0.050 Uiso 1 1 calc R . .
C16 C 0.4525(2) 0.3692(2) 0.4699(2) 0.0368(4) Uani 1 1 d . . .
C14 C 0.7678(2) 0.4126(3) 0.4353(2) 0.0383(5) Uani 1 1 d . . .
H14A H 0.8634 0.3659 0.4943 0.046 Uiso 1 1 calc R . .
H14B H 0.7675 0.5143 0.4749 0.046 Uiso 1 1 calc R . .
C3 C 0.8583(3) 0.6866(3) -0.1087(2) 0.0506(6) Uani 1 1 d . . .
H3 H 0.8579 0.7198 -0.1929 0.061 Uiso 1 1 calc R . .
C2 C 0.9819(3) 0.7093(3) 0.0231(3) 0.0494(5) Uani 1 1 d . . .
H2 H 1.0648 0.7574 0.0271 0.059 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
O2 C21 1.376(3) . ?
O2 C15 1.442(2) . ?
O1 C7 1.215(2) . ?
O3 C16 1.374(2) . ?
O3 C15 1.443(3) . ?
C8 C10 1.519(3) . ?
C8 C7 1.535(3) . ?
C8 C14 1.537(2) . ?
C8 H8 0.9800 . ?
C7 C6 1.495(3) . ?
N1 C9 1.332(3) . ?
N1 C13 1.344(3) . ?
C21 C20 1.367(3) . ?
C21 C16 1.381(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9300 . ?
C1 C2 1.377(3) . ?
C1 C6 1.401(3) . ?
C1 H1 0.9300 . ?
C11 C12 1.377(3) . ?
C11 C10 1.390(3) . ?
C11 H11 0.9300 . ?
C5 C4 1.384(3) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C17 C16 1.375(3) . ?
C17 C18 1.399(4) . ?
C17 H17 0.9300 . ?
C13 C12 1.383(3) . ?
C13 H13 0.9300 . ?
C20 C19 1.392(3) . ?
C20 H20 0.9300 . ?
C15 C14 1.498(3) . ?
C15 H15 0.9800 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C4 C3 1.383(3) . ?
C4 H4 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C3 C2 1.386(4) . ?
C3 H3 0.9300 . ?
C2 H2 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
C21 O2 C15 105.60(14) . . ?
C16 O3 C15 105.63(14) . . ?
C10 C8 C7 109.91(14) . . ?
C10 C8 C14 111.84(16) . . ?
C7 C8 C14 109.49(15) . . ?
C10 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C14 C8 H8 108.5 . . ?
O1 C7 C6 120.12(18) . . ?
O1 C7 C8 120.40(17) . . ?
C6 C7 C8 119.46(15) . . ?
C9 N1 C13 116.79(17) . . ?
C20 C21 O2 127.72(19) . . ?
C20 C21 C16 122.6(2) . . ?
O2 C21 C16 109.59(17) . . ?
N1 C9 C10 124.69(18) . . ?
N1 C9 H9 117.7 . . ?
C10 C9 H9 117.7 . . ?
C2 C1 C6 120.43(19) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C12 C11 C10 119.21(18) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C4 C5 C6 119.99(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 118.85(18) . . ?
C5 C6 C7 122.90(17) . . ?
C1 C6 C7 118.22(17) . . ?
C16 C17 C18 116.8(2) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 H17 121.6 . . ?
N1 C13 C12 122.91(19) . . ?
N1 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C21 C20 C19 116.6(2) . . ?
C21 C20 H20 121.7 . . ?
C19 C20 H20 121.7 . . ?
O2 C15 O3 106.38(14) . . ?
O2 C15 C14 109.25(17) . . ?
O3 C15 C14 111.40(18) . . ?
O2 C15 H15 109.9 . . ?
O3 C15 H15 109.9 . . ?
C14 C15 H15 109.9 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C11 C12 C13 119.23(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C18 C19 C20 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C11 C10 C9 117.11(18) . . ?
C11 C10 C8 122.00(16) . . ?
C9 C10 C8 120.88(17) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O3 C16 C17 128.8(2) . . ?
O3 C16 C21 109.87(18) . . ?
C17 C16 C21 121.3(2) . . ?
C15 C14 C8 112.81(16) . . ?
C15 C14 H14A 109.0 . . ?
C8 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C8 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?

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
C10 C8 C7 O1 -116.5(2) . . . . ?
C14 C8 C7 O1 6.7(3) . . . . ?
C10 C8 C7 C6 61.5(2) . . . . ?
C14 C8 C7 C6 -175.28(16) . . . . ?
C15 O2 C21 C20 171.7(2) . . . . ?
C15 O2 C21 C16 -11.6(2) . . . . ?
C13 N1 C9 C10 0.0(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 178.40(19) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C6 C7 -178.7(2) . . . . ?
O1 C7 C6 C5 -168.1(2) . . . . ?
C8 C7 C6 C5 13.9(3) . . . . ?
O1 C7 C6 C1 9.7(3) . . . . ?
C8 C7 C6 C1 -168.33(18) . . . . ?
C9 N1 C13 C12 2.1(3) . . . . ?
O2 C21 C20 C19 175.8(2) . . . . ?
C16 C21 C20 C19 -0.6(3) . . . . ?
C21 O2 C15 O3 17.0(2) . . . . ?
C21 O2 C15 C14 137.32(18) . . . . ?
C16 O3 C15 O2 -16.1(2) . . . . ?
C16 O3 C15 C14 -135.05(17) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
N1 C13 C12 C11 -2.2(3) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C21 C20 C19 C18 -0.5(4) . . . . ?
C12 C11 C10 C9 1.6(3) . . . . ?
C12 C11 C10 C8 -179.50(17) . . . . ?
N1 C9 C10 C11 -1.8(3) . . . . ?
N1 C9 C10 C8 179.33(17) . . . . ?
C7 C8 C10 C11 54.9(2) . . . . ?
C14 C8 C10 C11 -67.0(2) . . . . ?
C7 C8 C10 C9 -126.29(18) . . . . ?
C14 C8 C10 C9 111.87(19) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C15 O3 C16 C17 -173.7(2) . . . . ?
C15 O3 C16 C21 9.3(2) . . . . ?
C18 C17 C16 O3 -177.2(2) . . . . ?
C18 C17 C16 C21 -0.5(3) . . . . ?
C20 C21 C16 O3 178.4(2) . . . . ?
O2 C21 C16 O3 1.5(2) . . . . ?
C20 C21 C16 C17 1.2(3) . . . . ?
O2 C21 C16 C17 -175.78(19) . . . . ?
O2 C15 C14 C8 174.33(16) . . . . ?
O3 C15 C14 C8 -68.4(2) . . . . ?
C10 C8 C14 C15 -60.4(2) . . . . ?
C7 C8 C14 C15 177.49(17) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C4 C3 C2 C1 -0.4(4) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1006442'
