# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# 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,
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# from this site to visualise CIF-encoded structures and
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data_bpfdcn
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
5-(2-(benzyloxy)phenyl)furan-2,3-dicarbonitrile
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C19 H12 N2 O2'
_chemical_formula_sum 'C19 H12 N2 O2'
_chemical_formula_weight 300.31
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'
N N 0.0061 0.0033 '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 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
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 4.7455(19)
_cell_length_b 23.385(10)
_cell_length_c 15.884(7)
_cell_angle_alpha 90.00
_cell_angle_beta 96.403(7)
_cell_angle_gamma 90.00
_cell_volume 1751.7(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 113(2)
_cell_measurement_reflns_used 5198
_cell_measurement_theta_min 1.6
_cell_measurement_theta_max 27.8
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.139
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.075
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.801
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 113(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
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13869
_diffrn_reflns_av_R_equivalents 0.0444
_diffrn_reflns_av_sigmaI/netI 0.0422
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -27
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 1.56
_diffrn_reflns_theta_max 25.02
_reflns_number_total 3085
_reflns_number_gt 2334
_reflns_threshold_expression I>2\s(I)
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2008)'
_computing_publication_material
;SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009),
PublCIF (Westrip 2010)
;
_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.
Platon revealed a solvent accessible void in the structure and the disordered
solvent was removed using the SQUEEZE procedure details of which are recorded
below.
;
_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^)+(0.1316P)^2^+0.2092P] 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 0.041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3085
_refine_ls_number_parameters 252
_refine_ls_number_restraints 228
_refine_ls_R_factor_all 0.0791
_refine_ls_R_factor_gt 0.0648
_refine_ls_wR_factor_ref 0.2010
_refine_ls_wR_factor_gt 0.1861
_refine_ls_goodness_of_fit_ref 0.990
_refine_ls_restrained_S_all 1.066
_refine_ls_shift/su_max 0.030
_refine_ls_shift/su_mean 0.003
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 0.4458(8) 0.06056(12) 0.7226(2) 0.0942(15) Uani 0.707(5) 1 d PU A 1
H1 H 0.3780 0.0781 0.6703 0.113 Uiso 0.707(5) 1 calc PR A 1
C2 C 0.3409(8) 0.00737(12) 0.7428(2) 0.1211(18) Uani 0.707(5) 1 d PRU A 1
H2 H 0.2029 -0.0112 0.7043 0.145 Uiso 0.707(5) 1 calc PR A 1
C3 C 0.4380(8) -0.01864(12) 0.8192(2) 0.1057(18) Uani 0.707(5) 1 d PRU A 1
H3 H 0.3664 -0.0550 0.8330 0.127 Uiso 0.707(5) 1 calc PR A 1
C4 C 0.6400(8) 0.00854(12) 0.8755(2) 0.1120(19) Uani 0.707(5) 1 d PRU A 1
H4 H 0.7064 -0.0092 0.9278 0.134 Uiso 0.707(5) 1 calc PR A 1
C5 C 0.7449(8) 0.06172(12) 0.8554(2) 0.0925(16) Uani 0.707(5) 1 d PRU A 1
H5 H 0.8826 0.0800 0.8944 0.111 Uiso 0.707(5) 1 calc PR A 1
C6 C 0.6509(17) 0.0889(3) 0.7786(3) 0.0622(16) Uani 0.707(5) 1 d PU A 1
C1' C 0.455(3) 0.0595(6) 0.7755(10) 0.100(3) Uani 0.293(5) 1 d PU A 2
H1' H 0.3208 0.0796 0.7374 0.120 Uiso 0.293(5) 1 calc PR A 2
C2' C 0.393(4) 0.0054(7) 0.8006(11) 0.114(3) Uani 0.293(5) 1 d PU A 2
H2' H 0.2299 -0.0147 0.7760 0.136 Uiso 0.293(5) 1 calc PR A 2
C3' C 0.578(4) -0.0181(7) 0.8626(10) 0.099(3) Uani 0.293(5) 1 d PU A 2
H3' H 0.5275 -0.0533 0.8866 0.119 Uiso 0.293(5) 1 calc PR A 2
C4' C 0.849(3) 0.0078(6) 0.8945(9) 0.101(3) Uani 0.293(5) 1 d PU A 2
H4' H 0.9744 -0.0099 0.9376 0.122 Uiso 0.293(5) 1 calc PR A 2
C5' C 0.915(3) 0.0591(5) 0.8590(9) 0.087(3) Uani 0.293(5) 1 d PU A 2
H5' H 1.0965 0.0762 0.8713 0.104 Uiso 0.293(5) 1 calc PR A 2
C6' C 0.701(5) 0.0847(10) 0.8037(13) 0.076(3) Uani 0.293(5) 1 d PU A 2
C7 C 0.7516(6) 0.14574(11) 0.75980(16) 0.0573(7) Uani 1 1 d . . .
H7A H 0.9588 0.1486 0.7759 0.069 Uiso 1 1 calc R A 1
H7B H 0.7111 0.1540 0.6985 0.069 Uiso 1 1 calc R A 1
O1 O 0.6024(3) 0.18581(7) 0.80883(10) 0.0522(5) Uani 1 1 d . A .
C8 C 0.6390(5) 0.24272(10) 0.79634(14) 0.0462(6) Uani 1 1 d . . .
C9 C 0.8096(5) 0.26595(11) 0.73906(15) 0.0518(6) Uani 1 1 d . A .
H9 H 0.9094 0.2414 0.7050 0.062 Uiso 1 1 calc R . .
C10 C 0.8337(5) 0.32442(11) 0.73166(16) 0.0558(7) Uani 1 1 d . . .
H10 H 0.9518 0.3398 0.6928 0.067 Uiso 1 1 calc R A .
C11 C 0.6885(5) 0.36092(11) 0.77994(17) 0.0581(7) Uani 1 1 d . A .
H11 H 0.7061 0.4011 0.7740 0.070 Uiso 1 1 calc R . .
C12 C 0.5167(5) 0.33860(10) 0.83709(16) 0.0533(6) Uani 1 1 d . . .
H12 H 0.4164 0.3638 0.8701 0.064 Uiso 1 1 calc R A .
C13 C 0.4896(5) 0.27935(10) 0.84665(14) 0.0446(6) Uani 1 1 d . A .
C14 C 0.3100(5) 0.25606(10) 0.90667(14) 0.0437(6) Uani 1 1 d . . .
C15 C 0.2494(5) 0.20272(10) 0.93483(14) 0.0461(6) Uani 1 1 d . A .
H15 H 0.3247 0.1676 0.9174 0.055 Uiso 1 1 calc R . .
C16 C 0.0522(5) 0.20976(10) 0.99524(14) 0.0461(6) Uani 1 1 d . . .
C17 C 0.0044(5) 0.26698(10) 1.00093(14) 0.0463(6) Uani 1 1 d . A .
O2 O 0.1604(3) 0.29619(6) 0.94823(10) 0.0472(5) Uani 1 1 d . A .
C18 C -0.1737(5) 0.29796(11) 1.05094(16) 0.0532(7) Uani 1 1 d . . .
N1 N -0.3228(5) 0.32090(11) 1.09242(14) 0.0670(7) Uani 1 1 d . A .
C19 C -0.0860(5) 0.16674(11) 1.03907(15) 0.0543(7) Uani 1 1 d . A .
N2 N -0.2031(5) 0.13183(10) 1.07249(15) 0.0711(7) 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 0.141(4) 0.059(2) 0.083(3) 0.010(2) 0.013(3) -0.025(2)
C2 0.173(4) 0.080(3) 0.111(4) 0.016(3) 0.018(4) -0.029(3)
C3 0.146(4) 0.066(3) 0.112(4) 0.032(3) 0.047(3) 0.008(3)
C4 0.141(4) 0.094(3) 0.106(3) 0.027(3) 0.031(3) 0.010(4)
C5 0.112(4) 0.084(3) 0.085(3) 0.023(2) 0.024(3) 0.003(3)
C6 0.083(3) 0.051(2) 0.058(3) 0.004(2) 0.034(3) 0.006(2)
C1' 0.120(4) 0.075(4) 0.105(5) 0.005(4) 0.017(4) -0.012(4)
C2' 0.142(4) 0.088(4) 0.113(4) 0.016(4) 0.019(4) -0.016(4)
C3' 0.114(5) 0.077(5) 0.109(5) 0.005(5) 0.029(4) -0.016(5)
C4' 0.117(5) 0.085(4) 0.105(5) 0.016(4) 0.025(5) -0.015(5)
C5' 0.096(6) 0.074(5) 0.095(5) 0.012(4) 0.028(5) -0.023(5)
C6' 0.087(5) 0.061(5) 0.085(6) 0.004(5) 0.033(5) -0.007(4)
C7 0.0577(15) 0.0615(15) 0.0558(15) -0.0066(11) 0.0205(12) 0.0017(12)
O1 0.0545(10) 0.0513(10) 0.0540(10) -0.0039(7) 0.0206(8) -0.0025(7)
C8 0.0394(13) 0.0554(14) 0.0438(13) 0.0035(9) 0.0040(10) -0.0050(10)
C9 0.0446(14) 0.0690(16) 0.0428(13) 0.0038(11) 0.0095(10) -0.0033(11)
C10 0.0490(14) 0.0686(16) 0.0508(14) 0.0121(12) 0.0109(11) -0.0059(12)
C11 0.0563(16) 0.0558(15) 0.0629(16) 0.0131(11) 0.0103(12) -0.0078(12)
C12 0.0455(14) 0.0577(15) 0.0575(15) 0.0053(11) 0.0102(11) -0.0001(11)
C13 0.0380(12) 0.0536(13) 0.0424(12) 0.0045(10) 0.0051(10) -0.0007(10)
C14 0.0360(12) 0.0538(13) 0.0414(12) -0.0008(9) 0.0051(9) 0.0012(9)
C15 0.0424(13) 0.0537(13) 0.0427(13) 0.0023(9) 0.0068(10) 0.0014(10)
C16 0.0434(13) 0.0566(14) 0.0390(12) 0.0046(9) 0.0086(10) -0.0008(10)
C17 0.0408(12) 0.0597(15) 0.0395(12) 0.0010(10) 0.0097(10) -0.0014(10)
O2 0.0416(9) 0.0553(10) 0.0456(9) -0.0007(7) 0.0093(7) -0.0019(7)
C18 0.0472(15) 0.0650(16) 0.0483(14) -0.0017(11) 0.0089(11) -0.0019(11)
N1 0.0649(15) 0.0791(16) 0.0602(14) -0.0068(11) 0.0212(12) -0.0001(12)
C19 0.0541(15) 0.0634(16) 0.0472(14) 0.0064(11) 0.0131(11) 0.0005(12)
N2 0.0807(17) 0.0724(15) 0.0639(15) 0.0122(12) 0.0251(12) -0.0039(12)
_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 1.3900 . ?
C1 C6 1.408(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.405(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(8) . ?
C1' C6' 1.34(3) . ?
C1' C2' 1.37(2) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.36(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.46(2) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.375(17) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.40(2) . ?
C5' H5' 0.9500 . ?
C6' C7 1.62(2) . ?
C7 O1 1.452(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O1 C8 1.360(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.415(3) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.454(3) . ?
C14 C15 1.367(3) . ?
C14 O2 1.387(3) . ?
C15 C16 1.423(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.362(3) . ?
C16 C19 1.424(3) . ?
C17 O2 1.361(3) . ?
C17 C18 1.421(3) . ?
C18 N1 1.152(3) . ?
C19 N2 1.150(3) . ?
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 121.1(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 117.7(6) . . ?
C5 C6 C7 120.8(5) . . ?
C1 C6 C7 121.4(4) . . ?
C6' C1' C2' 121.0(16) . . ?
C6' C1' H1' 119.5 . . ?
C2' C1' H1' 119.5 . . ?
C3' C2' C1' 116.3(16) . . ?
C3' C2' H2' 121.9 . . ?
C1' C2' H2' 121.9 . . ?
C2' C3' C4' 123.8(15) . . ?
C2' C3' H3' 118.1 . . ?
C4' C3' H3' 118.1 . . ?
C5' C4' C3' 116.7(13) . . ?
C5' C4' H4' 121.6 . . ?
C3' C4' H4' 121.6 . . ?
C4' C5' C6' 116.6(15) . . ?
C4' C5' H5' 121.7 . . ?
C6' C5' H5' 121.7 . . ?
C5' C6' C1' 124.6(19) . . ?
C5' C6' C7 120.9(16) . . ?
C1' C6' C7 114.1(15) . . ?
O1 C7 C6' 103.5(8) . . ?
O1 C7 C6 106.8(3) . . ?
C6' C7 C6 15.8(9) . . ?
O1 C7 H7A 110.4 . . ?
C6' C7 H7A 98.0 . . ?
C6 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C6' C7 H7B 125.1 . . ?
C6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C8 O1 C7 118.39(18) . . ?
O1 C8 C9 124.7(2) . . ?
O1 C8 C13 115.47(19) . . ?
C9 C8 C13 119.8(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 118.7(2) . . ?
C12 C13 C14 120.6(2) . . ?
C8 C13 C14 120.7(2) . . ?
C15 C14 O2 108.91(19) . . ?
C15 C14 C13 135.8(2) . . ?
O2 C14 C13 115.29(19) . . ?
C14 C15 C16 107.1(2) . . ?
C14 C15 H15 126.5 . . ?
C16 C15 H15 126.5 . . ?
C17 C16 C15 106.6(2) . . ?
C17 C16 C19 124.9(2) . . ?
C15 C16 C19 128.4(2) . . ?
O2 C17 C16 110.26(19) . . ?
O2 C17 C18 119.1(2) . . ?
C16 C17 C18 130.7(2) . . ?
C17 O2 C14 107.18(17) . . ?
N1 C18 C17 177.1(3) . . ?
N2 C19 C16 178.1(3) . . ?
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 0.1(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 C7 177.0(3) . . . . ?
C2 C1 C6 C5 -0.2(7) . . . . ?
C2 C1 C6 C7 -177.0(4) . . . . ?
C6' C1' C2' C3' 8(3) . . . . ?
C1' C2' C3' C4' -8(3) . . . . ?
C2' C3' C4' C5' 1(2) . . . . ?
C3' C4' C5' C6' 8(2) . . . . ?
C4' C5' C6' C1' -9(3) . . . . ?
C4' C5' C6' C7 178.6(13) . . . . ?
C2' C1' C6' C5' 1(3) . . . . ?
C2' C1' C6' C7 173.8(14) . . . . ?
C5' C6' C7 O1 -102.7(17) . . . . ?
C1' C6' C7 O1 84.1(16) . . . . ?
C5' C6' C7 C6 153(5) . . . . ?
C1' C6' C7 C6 -20(3) . . . . ?
C5 C6 C7 O1 -76.2(6) . . . . ?
C1 C6 C7 O1 100.4(5) . . . . ?
C5 C6 C7 C6' 4(3) . . . . ?
C1 C6 C7 C6' -179(4) . . . . ?
C6' C7 O1 C8 170.2(8) . . . . ?
C6 C7 O1 C8 -173.8(3) . . . . ?
C7 O1 C8 C9 0.4(3) . . . . ?
C7 O1 C8 C13 -179.5(2) . . . . ?
O1 C8 C9 C10 -179.6(2) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C11 C12 C13 C14 179.9(2) . . . . ?
O1 C8 C13 C12 -179.9(2) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
O1 C8 C13 C14 -0.3(3) . . . . ?
C9 C8 C13 C14 179.9(2) . . . . ?
C12 C13 C14 C15 -175.5(2) . . . . ?
C8 C13 C14 C15 4.9(4) . . . . ?
C12 C13 C14 O2 3.6(3) . . . . ?
C8 C13 C14 O2 -175.98(18) . . . . ?
O2 C14 C15 C16 0.8(2) . . . . ?
C13 C14 C15 C16 179.9(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C14 C15 C16 C19 176.4(2) . . . . ?
C15 C16 C17 O2 -0.3(2) . . . . ?
C19 C16 C17 O2 -177.2(2) . . . . ?
C15 C16 C17 C18 179.7(2) . . . . ?
C19 C16 C17 C18 2.8(4) . . . . ?
C16 C17 O2 C14 0.8(2) . . . . ?
C18 C17 O2 C14 -179.19(19) . . . . ?
C15 C14 O2 C17 -1.0(2) . . . . ?
C13 C14 O2 C17 179.69(18) . . . . ?
O2 C17 C18 N1 171(5) . . . . ?
C16 C17 C18 N1 -9(6) . . . . ?
C17 C16 C19 N2 94(8) . . . . ?
C15 C16 C19 N2 -82(8) . . . . ?
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
C9 H9 N1 0.95 2.73 3.674(4) 173.5 4_765
C10 H10 N2 0.95 2.73 3.676(4) 171.6 4_765
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.327
_refine_diff_density_min -0.264
_refine_diff_density_rms 0.045
# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.034 0.500 0.000 127 27 ' '
2 -0.026 0.000 0.500 127 27 ' '
_platon_squeeze_details
;
Disordered solvent removed using the SQUEEZE procedure
and solvent free reflection data used for the final refinment.
;
_iucr_refine_instructions_details
;
TITL shelx in P2(1)/n
CELL 0.71073 4.7455 23.3850 15.8840 90.000 96.403 90.000
ZERR 4.00 0.0019 0.0095 0.0066 0.000 0.007 0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 76 48 8 8
OMIT -3.00 50.04
L.S. 12
ACTA
BOND $h
FMAP 2
PLAN 5
size 0.30 0.04 0.04
simu 0.01 c1 c2 c3 c4 c5 c6 c1' c2' c3' c4' c5' c6'
isor 0.01 c1 c2 c3 c4 c5 c6 c1' c2' c3' c4' c5' c6'
eqiv $1 1.5+x,1/2-y,-1/2+z
htab C9 N1_$1
htab c10 n2_$1
conf
mpla c1' c2' c3' c4' c5' c6'
mpla c1 c2 c3 c4 c5 c6
mpla c8 c9 c10 c11 c12 c13
mpla 5 c14 c15 c16 c17 o2 c18 n1 c19 n2
mpla
TEMP -160
WGHT 0.131600 0.209200
EXTI 0.041487
FVAR 8.00851 0.70745
PART 1
C1 1 0.445816 0.060556 0.722643 21.00000 0.14105 0.05924 =
0.08262 0.00954 0.01342 -0.02455
AFIX 43
H1 2 0.378022 0.078066 0.670310 21.00000 -1.20000
AFIX 0
C2 1 0.340934 0.007372 0.742757 21.00000 0.17350 0.07960 =
0.11079 0.01561 0.01784 -0.02923
AFIX 43
H2 2 0.202889 -0.011202 0.704253 21.00000 -1.20000
AFIX 0
C3 1 0.438033 -0.018636 0.819209 21.00000 0.14649 0.06604 =
0.11183 0.03238 0.04702 0.00810
AFIX 43
H3 2 0.366350 -0.054985 0.832956 21.00000 -1.20000
AFIX 0
C4 1 0.640014 0.008540 0.875547 21.00000 0.14081 0.09369 =
0.10552 0.02724 0.03149 0.00977
AFIX 43
H4 2 0.706376 -0.009235 0.927799 21.00000 -1.20000
AFIX 0
C5 1 0.744899 0.061724 0.855434 21.00000 0.11200 0.08377 =
0.08454 0.02334 0.02380 0.00270
AFIX 43
H5 2 0.882617 0.080013 0.894378 21.00000 -1.20000
AFIX 0
C6 1 0.650890 0.088906 0.778557 21.00000 0.08326 0.05113 =
0.05822 0.00426 0.03433 0.00560
PART 2
C1' 1 0.454567 0.059528 0.775453 -21.00000 0.11974 0.07539 =
0.10484 0.00526 0.01699 -0.01178
AFIX 43
H1' 2 0.320808 0.079585 0.737410 -21.00000 -1.20000
AFIX 0
C2' 1 0.392802 0.005388 0.800551 -21.00000 0.14163 0.08763 =
0.11279 0.01584 0.01943 -0.01605
AFIX 43
H2' 2 0.229868 -0.014664 0.776006 -21.00000 -1.20000
AFIX 0
C3' 1 0.577672 -0.018086 0.862572 -21.00000 0.11444 0.07695 =
0.10933 0.00484 0.02906 -0.01567
AFIX 43
H3' 2 0.527483 -0.053349 0.886586 -21.00000 -1.20000
AFIX 0
C4' 1 0.849467 0.007814 0.894481 -21.00000 0.11688 0.08522 =
0.10504 0.01649 0.02531 -0.01510
AFIX 43
H4' 2 0.974441 -0.009913 0.937622 -21.00000 -1.20000
AFIX 0
C5' 1 0.915140 0.059075 0.858962 -21.00000 0.09595 0.07438 =
0.09461 0.01172 0.02807 -0.02256
AFIX 43
H5' 2 1.096493 0.076245 0.871250 -21.00000 -1.20000
AFIX 0
C6' 1 0.700858 0.084677 0.803725 -21.00000 0.08661 0.06121 =
0.08485 0.00362 0.03334 -0.00692
PART 0
C7 1 0.751619 0.145744 0.759801 11.00000 0.05772 0.06152 =
0.05580 -0.00657 0.02045 0.00172
AFIX 23
H7A 2 0.958789 0.148581 0.775867 11.00000 -1.20000
H7B 2 0.711076 0.154034 0.698527 11.00000 -1.20000
AFIX 0
O1 4 0.602447 0.185811 0.808832 11.00000 0.05451 0.05133 =
0.05404 -0.00386 0.02059 -0.00252
C8 1 0.639042 0.242725 0.796340 11.00000 0.03935 0.05542 =
0.04379 0.00351 0.00404 -0.00499
C9 1 0.809561 0.265949 0.739063 11.00000 0.04457 0.06903 =
0.04284 0.00375 0.00949 -0.00333
AFIX 43
H9 2 0.909406 0.241426 0.705041 11.00000 -1.20000
AFIX 0
C10 1 0.833681 0.324420 0.731662 11.00000 0.04902 0.06864 =
0.05079 0.01210 0.01086 -0.00587
AFIX 43
H10 2 0.951835 0.339850 0.692815 11.00000 -1.20000
AFIX 0
C11 1 0.688452 0.360919 0.779941 11.00000 0.05635 0.05578 =
0.06288 0.01307 0.01028 -0.00782
AFIX 43
H11 2 0.706139 0.401146 0.774036 11.00000 -1.20000
AFIX 0
C12 1 0.516667 0.338600 0.837087 11.00000 0.04554 0.05771 =
0.05754 0.00531 0.01023 -0.00006
AFIX 43
H12 2 0.416361 0.363751 0.870065 11.00000 -1.20000
AFIX 0
C13 1 0.489631 0.279352 0.846651 11.00000 0.03801 0.05360 =
0.04242 0.00447 0.00512 -0.00074
C14 1 0.309994 0.256064 0.906671 11.00000 0.03596 0.05381 =
0.04139 -0.00084 0.00515 0.00124
C15 1 0.249400 0.202719 0.934832 11.00000 0.04236 0.05373 =
0.04267 0.00228 0.00678 0.00145
AFIX 43
H15 2 0.324749 0.167571 0.917369 11.00000 -1.20000
AFIX 0
C16 1 0.052174 0.209760 0.995239 11.00000 0.04342 0.05665 =
0.03903 0.00458 0.00864 -0.00080
C17 1 0.004433 0.266982 1.000932 11.00000 0.04079 0.05970 =
0.03950 0.00105 0.00972 -0.00135
O2 4 0.160409 0.296192 0.948233 11.00000 0.04159 0.05530 =
0.04560 -0.00071 0.00932 -0.00194
C18 1 -0.173714 0.297956 1.050937 11.00000 0.04724 0.06495 =
0.04833 -0.00165 0.00889 -0.00191
N1 3 -0.322806 0.320904 1.092420 11.00000 0.06495 0.07907 =
0.06024 -0.00682 0.02123 -0.00014
C19 1 -0.086031 0.166736 1.039067 11.00000 0.05414 0.06340 =
0.04716 0.00637 0.01309 0.00054
N2 3 -0.203147 0.131826 1.072486 11.00000 0.08069 0.07245 =
0.06391 0.01219 0.02514 -0.00390
REM shelx in P2(1)/n
REM R1 = 0.0648 for 2334 Fo > 4sig(Fo) and 0.0791 for all 3085 data
REM 252 parameters refined using 228 restraints
WGHT 0.1207 0.1190
REM Highest difference peak 0.327, deepest hole -0.264, 1-sigma level 0.045
HKLF 4
END
;
_database_code_depnum_ccdc_archive 'CCDC 952813'