# Electronic Supplementary Material (ESI) for RSC Advances.
# 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/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_aw30m
_database_code_depnum_ccdc_archive 'CCDC 1020845'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-methyl-3-(5-methoxybenzofuran-2-yl)acrylate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O4'
_chemical_formula_sum            'C14 H14 O4'
_chemical_formula_weight         246.25

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0907(15)
_cell_length_b                   8.1765(15)
_cell_length_c                   10.6283(19)
_cell_angle_alpha                91.440(3)
_cell_angle_beta                 101.366(3)
_cell_angle_gamma                114.809(3)
_cell_volume                     621.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2721
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;


_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6041
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2189
_reflns_number_gt                1932
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0541P)²+0.1310P] 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         2189
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 1.1476(3) 0.7391(3) 1.2631(2) 0.0711(6) Uani 1 1 d . . .
H1A H 1.1661 0.6827 1.1901 0.107 Uiso 1 1 calc R . .
H1B H 1.2668 0.8154 1.3189 0.107 Uiso 1 1 calc R . .
H1C H 1.0831 0.8111 1.2335 0.107 Uiso 1 1 calc R . .
C2 C 0.8696(2) 0.4734(2) 1.26547(17) 0.0481(4) Uani 1 1 d . . .
C3 C 0.7790(2) 0.3372(2) 1.33799(17) 0.0520(4) Uani 1 1 d . . .
H3 H 0.8360 0.3421 1.4239 0.062 Uiso 1 1 calc R . .
C4 C 0.6078(2) 0.1966(2) 1.28525(16) 0.0507(4) Uani 1 1 d . . .
H4 H 0.5478 0.1054 1.3332 0.061 Uiso 1 1 calc R . .
C5 C 0.5287(2) 0.1967(2) 1.15778(16) 0.0428(4) Uani 1 1 d . . .
C6 C 0.6147(2) 0.3283(2) 1.08350(16) 0.0425(4) Uani 1 1 d . . .
C7 C 0.7902(2) 0.4719(2) 1.13849(17) 0.0485(4) Uani 1 1 d . . .
H7 H 0.8505 0.5628 1.0905 0.058 Uiso 1 1 calc R . .
C8 C 0.4903(2) 0.2782(2) 0.95957(16) 0.0464(4) Uani 1 1 d . . .
H8 H 0.5085 0.3406 0.8878 0.056 Uiso 1 1 calc R . .
C9 C 0.3411(2) 0.1234(2) 0.96543(15) 0.0436(4) Uani 1 1 d . . .
C10 C 0.1760(2) 0.0101(2) 0.86993(16) 0.0448(4) Uani 1 1 d . . .
H10 H 0.1655 0.0454 0.7874 0.054 Uiso 1 1 calc R . .
C11 C 0.0370(2) -0.1404(2) 0.88836(17) 0.0476(4) Uani 1 1 d . . .
H11 H 0.0448 -0.1740 0.9715 0.057 Uiso 1 1 calc R . .
C12 C -0.1273(2) -0.2577(2) 0.78897(17) 0.0473(4) Uani 1 1 d . . .
C13 C -0.2811(3) -0.3111(3) 0.56879(19) 0.0637(5) Uani 1 1 d . . .
H13A H -0.4010 -0.3434 0.5906 0.076 Uiso 1 1 calc R . .
H13B H -0.2681 -0.4217 0.5516 0.076 Uiso 1 1 calc R . .
C14 C -0.2706(4) -0.2135(4) 0.4543(2) 0.0977(9) Uani 1 1 d . . .
H14A H -0.2860 -0.1055 0.4717 0.147 Uiso 1 1 calc R . .
H14B H -0.3679 -0.2901 0.3824 0.147 Uiso 1 1 calc R . .
H14C H -0.1511 -0.1810 0.4341 0.147 Uiso 1 1 calc R . .
O1 O 1.03976(18) 0.60335(18) 1.33202(13) 0.0644(4) Uani 1 1 d . . .
O2 O 0.35961(15) 0.06871(15) 1.08721(11) 0.0463(3) Uani 1 1 d . . .
O3 O -0.24663(18) -0.39842(18) 0.80751(13) 0.0644(4) Uani 1 1 d . . .
O4 O -0.13137(16) -0.19333(16) 0.67457(11) 0.0552(4) Uani 1 1 d . . .

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 0.0545(12) 0.0531(12) 0.0820(15) 0.0102(11) 0.0024(11) 0.0065(9)
C2 0.0462(10) 0.0472(10) 0.0479(10) -0.0001(8) 0.0053(8) 0.0201(8)
C3 0.0543(10) 0.0590(11) 0.0390(9) 0.0041(8) 0.0041(8) 0.0239(9)
C4 0.0536(10) 0.0535(10) 0.0432(10) 0.0109(8) 0.0129(8) 0.0204(9)
C5 0.0406(9) 0.0432(9) 0.0444(9) 0.0030(7) 0.0089(7) 0.0185(7)
C6 0.0438(9) 0.0427(9) 0.0450(9) 0.0069(7) 0.0106(7) 0.0224(8)
C7 0.0483(10) 0.0432(9) 0.0509(10) 0.0093(8) 0.0108(8) 0.0169(8)
C8 0.0488(10) 0.0493(10) 0.0429(9) 0.0113(7) 0.0099(8) 0.0227(8)
C9 0.0469(9) 0.0468(9) 0.0406(9) 0.0062(7) 0.0095(7) 0.0236(8)
C10 0.0474(9) 0.0497(10) 0.0405(9) 0.0059(7) 0.0098(7) 0.0242(8)
C11 0.0504(10) 0.0517(10) 0.0426(9) 0.0066(8) 0.0118(8) 0.0232(9)
C12 0.0457(9) 0.0476(10) 0.0516(10) 0.0055(8) 0.0135(8) 0.0219(8)
C13 0.0554(11) 0.0660(12) 0.0547(11) -0.0060(9) -0.0021(9) 0.0193(10)
C14 0.1000(19) 0.102(2) 0.0552(13) 0.0112(13) -0.0097(13) 0.0220(16)
O1 0.0540(8) 0.0601(8) 0.0562(8) 0.0038(6) -0.0009(6) 0.0090(6)
O2 0.0443(6) 0.0476(7) 0.0422(6) 0.0078(5) 0.0078(5) 0.0162(5)
O3 0.0551(8) 0.0547(8) 0.0690(9) 0.0102(7) 0.0151(7) 0.0095(7)
O4 0.0521(7) 0.0550(7) 0.0448(7) 0.0041(6) 0.0023(6) 0.0140(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 O1 1.418(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.370(2) . ?
C2 C7 1.373(2) . ?
C2 C3 1.397(3) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 O2 1.3727(19) . ?
C5 C6 1.377(2) . ?
C6 C7 1.405(2) . ?
C6 C8 1.421(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(2) . ?
C8 H8 0.9300 . ?
C9 O2 1.3809(19) . ?
C9 C10 1.433(2) . ?
C10 C11 1.325(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.459(2) . ?
C11 H11 0.9300 . ?
C12 O3 1.204(2) . ?
C12 O4 1.337(2) . ?
C13 O4 1.445(2) . ?
C13 C14 1.469(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.55(16) . . ?
O1 C2 C3 114.22(15) . . ?
C7 C2 C3 121.23(16) . . ?
C4 C3 C2 121.42(16) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 116.93(16) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
O2 C5 C6 110.85(14) . . ?
O2 C5 C4 126.07(15) . . ?
C6 C5 C4 123.08(16) . . ?
C5 C6 C7 119.53(15) . . ?
C5 C6 C8 105.54(15) . . ?
C7 C6 C8 134.93(16) . . ?
C2 C7 C6 117.80(16) . . ?
C2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C9 C8 C6 107.25(15) . . ?
C9 C8 H8 126.4 . . ?
C6 C8 H8 126.4 . . ?
C8 C9 O2 111.00(14) . . ?
C8 C9 C10 131.85(16) . . ?
O2 C9 C10 117.13(14) . . ?
C11 C10 C9 126.04(16) . . ?
C11 C10 H10 117.0 . . ?
C9 C10 H10 117.0 . . ?
C10 C11 C12 125.37(17) . . ?
C10 C11 H11 117.3 . . ?
C12 C11 H11 117.3 . . ?
O3 C12 O4 123.32(17) . . ?
O3 C12 C11 123.66(17) . . ?
O4 C12 C11 113.02(15) . . ?
O4 C13 C14 108.07(18) . . ?
O4 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O4 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 C1 117.93(15) . . ?
C5 O2 C9 105.36(12) . . ?
C12 O4 C13 115.84(15) . . ?

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
O1 C2 C3 C4 -179.65(16) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 O2 179.79(15) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
O2 C5 C6 C7 -179.94(13) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
O2 C5 C6 C8 0.10(17) . . . . ?
C4 C5 C6 C8 179.23(15) . . . . ?
O1 C2 C7 C6 179.66(15) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C8 C6 C7 C2 -179.57(17) . . . . ?
C5 C6 C8 C9 -0.25(18) . . . . ?
C7 C6 C8 C9 179.80(17) . . . . ?
C6 C8 C9 O2 0.31(18) . . . . ?
C6 C8 C9 C10 -178.38(17) . . . . ?
C8 C9 C10 C11 -179.63(18) . . . . ?
O2 C9 C10 C11 1.7(2) . . . . ?
C9 C10 C11 C12 -177.82(15) . . . . ?
C10 C11 C12 O3 176.12(18) . . . . ?
C10 C11 C12 O4 -3.5(2) . . . . ?
C7 C2 O1 C1 -4.5(3) . . . . ?
C3 C2 O1 C1 175.34(17) . . . . ?
C6 C5 O2 C9 0.08(17) . . . . ?
C4 C5 O2 C9 -179.02(16) . . . . ?
C8 C9 O2 C5 -0.25(17) . . . . ?
C10 C9 O2 C5 178.66(13) . . . . ?
O3 C12 O4 C13 -5.3(3) . . . . ?
C11 C12 O4 C13 174.37(15) . . . . ?
C14 C13 O4 C12 176.19(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
