##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-methoxybenzaldehyde
;
_chemical_name_common     'anisaldehyde'
_chemical_formula_moiety     'C8 H8 O2'
_chemical_formula_sum     'C8 H8 O2'
_chemical_formula_iupac     'C8 H8 O2'
_chemical_formula_weight     136.14
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.970(4)
_cell_length_b     9.034(9)
_cell_length_c     15.544(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     697.9(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     637
_cell_measurement_theta_min     2.62
_cell_measurement_theta_max     22.78
_cell_measurement_temperature     203.0(10)
_exptl_crystal_description     cylinder
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.296
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     288
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     .
_exptl_absorpt_correction_T_max     .
_exptl_special_details
;
The crystallization was performed on the diffractometer at a temperature of 263
K with a miniature zone melting procedure using focused infrared-laser-
radiation according to (Boese, 1994).
;
_diffrn_ambient_temperature     203.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
          'Siemens SMART three-axis goniometer with APEXII area-detector system'
_diffrn_measurement_method
                            'Data collection strategy APEX 2/COSMO with chi = 0'
_diffrn_detector_area_resol_mean     512
_diffrn_reflns_number     2015
_diffrn_reflns_av_R_equivalents     0.0692
_diffrn_reflns_av_sigmaI/netI     0.0737
_diffrn_reflns_theta_min     2.61
_diffrn_reflns_theta_max     23.98
_diffrn_reflns_theta_full     23.98
_diffrn_measured_fraction_theta_max     0.810
_diffrn_measured_fraction_theta_full     0.810
_diffrn_reflns_limit_h_min     -3
_diffrn_reflns_limit_h_max     3
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     3
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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. Treatment of hydrogen atoms Riding model on idealized geometrics
with the 1.2 fold isotropic displacement parameters of the equivalent
Uij of the corresponding carbon atom. The methyl groups are idealized
with tetrahedral angles in a combined rotating and rigid group refinement with
the 1.5 fold isotropic displacement parameters of the equivalent Uij
of the corresponding carbon atom.
;
_reflns_number_total     885
_reflns_number_gt     705
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0536
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.0653
_refine_ls_wR_factor_ref     0.0710
_refine_ls_goodness_of_fit_ref     0.940
_refine_ls_restrained_S_all     0.940
_refine_ls_number_reflns     885
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0204P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.118
_refine_diff_density_min     -0.126
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.012(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 [or SAINT?] (Bruker, 2006)'
_computing_structure_solution     'APEX2 (Bruker, 2006)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.0019(4) -0.0164(2) 0.53640(11) 0.0593(6) Uani d . 1 1 . .
    C C7 0.8823(5) -0.0842(3) 0.48084(15) 0.0464(8) Uani d . 1 1 . .
    H H7 0.9283 -0.1867 0.4739 0.056 Uiso d R 1 1 . .
    C C1 0.6769(5) -0.0255(3) 0.42348(13) 0.0369(7) Uani d . 1 1 . .
    C C2 0.5485(6) -0.1195(3) 0.36659(14) 0.0422(7) Uani d . 1 1 . .
    H H2 0.5988 -0.2220 0.3664 0.051 Uiso d R 1 1 . .
    C C3 0.3539(6) -0.0705(2) 0.30975(14) 0.0391(8) Uani d . 1 1 . .
    H H3 0.2692 -0.1383 0.2707 0.047 Uiso d R 1 1 . .
    C C4 0.2870(5) 0.0793(3) 0.31038(14) 0.0347(7) Uani d . 1 1 . .
    C C5 0.4129(6) 0.1759(3) 0.36761(14) 0.0414(7) Uani d . 1 1 . .
    H H5 0.3631 0.2786 0.3685 0.050 Uiso d R 1 1 . .
    C C6 0.6059(6) 0.1246(3) 0.42320(13) 0.0419(7) Uani d . 1 1 . .
    H H6 0.6969 0.1915 0.4614 0.050 Uiso d R 1 1 . .
    O O2 0.1022(3) 0.14176(18) 0.25731(9) 0.0455(6) Uani d . 1 1 . .
    C C8 -0.0230(6) 0.0499(3) 0.19443(14) 0.0498(8) Uani d . 1 1 . .
    H H8A 0.1129 0.0015 0.1596 0.075 Uiso d R 1 1 . .
    H H8B -0.1371 0.1102 0.1579 0.075 Uiso d R 1 1 . .
    H H8C -0.1315 -0.0244 0.2232 0.075 Uiso d R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0564(15) 0.0673(13) 0.0530(9) 0.0061(12) -0.0073(10) 0.0009(10)
    C7 0.047(2) 0.0471(17) 0.0448(14) 0.0043(15) 0.0084(13) 0.0037(13)
    C1 0.0349(19) 0.0400(14) 0.0357(12) 0.0009(13) 0.0065(12) 0.0024(12)
    C2 0.048(2) 0.0338(15) 0.0450(13) 0.0046(13) 0.0095(14) 0.0012(12)
    C3 0.044(2) 0.0339(14) 0.0395(13) -0.0029(14) 0.0022(13) -0.0050(11)
    C4 0.032(2) 0.0390(14) 0.0336(12) -0.0008(12) 0.0030(12) 0.0072(12)
    C5 0.047(2) 0.0304(14) 0.0466(14) 0.0018(13) -0.0008(14) 0.0006(12)
    C6 0.048(2) 0.0380(15) 0.0392(13) -0.0052(14) -0.0028(14) -0.0024(12)
    O2 0.0449(15) 0.0435(11) 0.0481(10) 0.0000(10) -0.0052(10) 0.0025(8)
    C8 0.045(2) 0.0576(16) 0.0472(13) -0.0070(15) -0.0094(12) -0.0003(14)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.214(3) ?
    C7 C1 . 1.455(3) ?
    C7 H7 . 0.9601 ?
    C1 C2 . 1.382(3) ?
    C1 C6 . 1.402(4) ?
    C2 C3 . 1.383(3) ?
    C2 H2 . 0.9600 ?
    C3 C4 . 1.394(3) ?
    C3 H3 . 0.9601 ?
    C4 O2 . 1.357(3) ?
    C4 C5 . 1.394(3) ?
    C5 C6 . 1.372(3) ?
    C5 H5 . 0.9600 ?
    C6 H6 . 0.9600 ?
    O2 C8 . 1.425(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C8 H8C . 0.9699 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C7 C1 . . 126.6(3) ?
    O1 C7 H7 . . 116.8 ?
    C1 C7 H7 . . 116.7 ?
    C2 C1 C6 . . 118.4(2) ?
    C2 C1 C7 . . 119.5(2) ?
    C6 C1 C7 . . 122.1(2) ?
    C3 C2 C1 . . 122.4(2) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 118.3 ?
    C2 C3 C4 . . 118.2(2) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 121.3 ?
    O2 C4 C5 . . 115.5(2) ?
    O2 C4 C3 . . 124.1(2) ?
    C5 C4 C3 . . 120.3(3) ?
    C6 C5 C4 . . 120.3(2) ?
    C6 C5 H5 . . 119.8 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 120.3(2) ?
    C5 C6 H6 . . 120.4 ?
    C1 C6 H6 . . 119.2 ?
    C4 O2 C8 . . 118.04(19) ?
    O2 C8 H8A . . 110.0 ?
    O2 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 109.5 ?
    O2 C8 H8C . . 109.2 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C7 C1 C2 . . . . -176.4(2) ?
    O1 C7 C1 C6 . . . . 4.3(4) ?
    C6 C1 C2 C3 . . . . 0.1(4) ?
    C7 C1 C2 C3 . . . . -179.3(2) ?
    C1 C2 C3 C4 . . . . 0.1(4) ?
    C2 C3 C4 O2 . . . . 179.19(19) ?
    C2 C3 C4 C5 . . . . -0.5(4) ?
    O2 C4 C5 C6 . . . . -179.0(2) ?
    C3 C4 C5 C6 . . . . 0.7(4) ?
    C4 C5 C6 C1 . . . . -0.5(4) ?
    C2 C1 C6 C5 . . . . 0.1(4) ?
    C7 C1 C6 C5 . . . . 179.4(2) ?
    C5 C4 O2 C8 . . . . 176.8(2) ?
    C3 C4 O2 C8 . . . . -2.9(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C3 H3 O2 3_545 0.96 2.75 3.603(4) 148.9
    C5 H5 O1 4_456 0.96 2.70 3.447(4) 135.3
    C8 H8A O1 2_654 0.97 2.71 3.582(4) 149.8
    C8 H8B O1 2_554 0.97 2.75 3.434(4) 127.8
_iucr_refine_instructions_details
;
TITL C8 H8 O2  in P2(1)2(1)2(1) at 203K
CELL 0.71073   4.9702   9.0340  15.5439  90.000  90.000  90.000
ZERR    4.00   0.0042   0.0087   0.0144   0.000   0.000   0.000
LATT -1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C H O
UNIT 32 32 8
TEMP -70.000
ACTA
OMIT 3 1 2
OMIT 1 3 0
SIZE 0.300 0.300 0.300
L.S. 8
BOND $H
CONF
EQIV $1 '1-x, -1/2+y, 1/2-z'
EQIV $2 '-x, -1/2+y, 1/2-z'
EQIV $3 '-1/2+x, 1/2-y, 1-z'
EQIV $4 '3/2-x, -y, -1/2+z'
EQIV $5 '1/2-x, -y, -1/2+z'
HTAB C2 O2_$1
HTAB C3 O2_$2
HTAB C5 O1_$3
HTAB C8 O1_$4
HTAB C8 O1_$5
FMAP 2
PLAN 10
WGHT      0.0204      0.0000
EXTI    0.014291
FVAR       1.04175
O1    3    1.001702   -0.016463    0.536386    11.00000    0.05672    0.06831 =
         0.05310    0.00125   -0.00753    0.00615
C7    1    0.882412   -0.084177    0.480878    11.00000    0.04763    0.04695 =
         0.04479    0.00341    0.00829    0.00332
AFIX   3
H7    2    0.928322   -0.186706    0.473918    11.00000   -1.20000
AFIX   0
C1    1    0.677003   -0.025493    0.423469    11.00000    0.03443    0.04003 =
         0.03633    0.00269    0.00645    0.00108
C2    1    0.548296   -0.119457    0.366465    11.00000    0.04805    0.03377 =
         0.04507    0.00090    0.00958    0.00439
AFIX   3
H2    2    0.598615   -0.222047    0.366265    11.00000   -1.20000
AFIX   0
C3    1    0.353828   -0.070678    0.309728    11.00000    0.04280    0.03416 =
         0.03953   -0.00432    0.00210   -0.00227
AFIX   3
H3    2    0.269058   -0.138468    0.270638    11.00000   -1.20000
AFIX   0
C4    1    0.286919    0.079459    0.310383    11.00000    0.03220    0.03895 =
         0.03344    0.00682    0.00321   -0.00127
C5    1    0.412469    0.175947    0.367603    11.00000    0.04650    0.03085 =
         0.04661    0.00083   -0.00078    0.00184
AFIX   3
H5    2    0.362669    0.278607    0.368493    11.00000   -1.20000
AFIX   0
C6    1    0.605867    0.124628    0.423131    11.00000    0.04831    0.03850 =
         0.03923   -0.00271   -0.00199   -0.00604
AFIX   3
H6    2    0.696887    0.191478    0.461311    11.00000   -1.20000
AFIX   0
O2    3    0.102151    0.141803    0.257320    11.00000    0.04519    0.04343 =
         0.04815    0.00266   -0.00560    0.00007
C8    1   -0.023412    0.049957    0.194455    11.00000    0.04478    0.05775 =
         0.04681    0.00020   -0.00878   -0.00713
AFIX   3
H8A   2    0.112478    0.001607    0.159575    11.00000   -1.50000
H8B   2   -0.137492    0.110337    0.157955    11.00000   -1.50000
H8C   2   -0.131952   -0.024303    0.223205    11.00000   -1.50000
HKLF 4
REM  C8 H8 O2  in P2(1)2(1)2(1)
REM R1 =  0.0361 for    706 Fo > 4sig(Fo)  and  0.0537 for all    886 data
REM     92 parameters refined using      0 restraints
END
REM Highest difference peak  0.119,  deepest hole -0.128,  1-sigma level  0.034
Q1    1   0.9174 -0.0538  0.6034  11.00000  0.05    0.12
Q2    1   0.4460  0.1763  0.4831  11.00000  0.05    0.11
Q3    1   0.4479  0.0186  0.1574  11.00000  0.05    0.11
Q4    1   0.7752  0.1239  0.3215  11.00000  0.05    0.10
Q5    1  -0.0670 -0.0413  0.3193  11.00000  0.05    0.10
Q6    1   0.0621  0.0083  0.1381  11.00000  0.05    0.10
Q7    1  -0.2237  0.0359  0.2935  11.00000  0.05    0.10
Q8    1   0.3745  0.1228  0.4490  11.00000  0.05    0.09
Q9    1   0.2184 -0.0648  0.0789  11.00000  0.05    0.09
Q10   1  -0.1031  0.0741  0.2549  11.00000  0.05    0.09
;
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-hydroxybenzaldehyde
;
_chemical_name_common     'Salicylylaldehyde'
_chemical_formula_moiety     'C7 H6 O2'
_chemical_formula_sum     'C7 H6 O2'
_chemical_formula_iupac     'C7 H6 O2'
_chemical_formula_weight     122.12
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/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     6.3945(3)
_cell_length_b     13.8939(9)
_cell_length_c     6.9172(4)
_cell_angle_alpha     90.00
_cell_angle_beta     103.262(3)
_cell_angle_gamma     90.00
_cell_volume     598.17(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1182
_cell_measurement_theta_min     2.94
_cell_measurement_theta_max     24.35
_cell_measurement_temperature     233(2)
_exptl_crystal_description     cylinder
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.3
_exptl_crystal_density_diffrn     1.356
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     256
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     .
_exptl_absorpt_correction_T_max     .
_exptl_special_details
;
The crystallization was performed on the diffractometer at a temperature of 253
K with a miniature zone melting procedure using focused infrared-laser-
radiation according to (Boese, 1994).
;
_diffrn_ambient_temperature     233(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
          'Siemens SMART three-axis goniometer with APEXII area-detector system'
_diffrn_measurement_method
                             'Data collection strategy APEX2/COSMO with chi = 0'
_diffrn_detector_area_resol_mean     512
_diffrn_reflns_number     8643
_diffrn_reflns_av_R_equivalents     0.0556
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_theta_min     2.93
_diffrn_reflns_theta_max     36.24
_diffrn_reflns_theta_full     24.00
_diffrn_measured_fraction_theta_max     0.641
_diffrn_measured_fraction_theta_full     0.844
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -5
_diffrn_reflns_limit_l_max     5
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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. Treatment of hydrogen atom: Riding model on idealized geometries
with the 1.2 fold isotropic displacement parameters of the equivalent
Uij of the corresponding carbon atom. Hydroxy hydrogen atom position
taken from a Fourier-map and also refined as riding group with the 1.5 fold
isotropic displacement parameters of the equivalent Uij of the
corresponding hydroxy atom.
;
_reflns_number_total     1853
_reflns_number_gt     1002
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1095
_refine_ls_R_factor_gt     0.0573
_refine_ls_wR_factor_gt     0.1511
_refine_ls_wR_factor_ref     0.1850
_refine_ls_goodness_of_fit_ref     0.998
_refine_ls_restrained_S_all     0.998
_refine_ls_number_reflns     1853
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.1022P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.317
_refine_diff_density_min     -0.183
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 [or SAINT?] (Bruker, 2006)'
_computing_structure_solution     'APEX2 (Bruker, 2006)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.2556(2) 0.54061(8) 0.6616(2) 0.0596(5) Uani d . 1 1 . .
    O O2 0.55260(18) 0.67452(9) 0.7310(2) 0.0587(5) Uani d . 1 1 . .
    H H2 0.4655 0.6080 0.7059 0.088 Uiso d R 1 1 . .
    C C1 0.1738(2) 0.70760(10) 0.6451(3) 0.0341(5) Uani d . 1 1 . .
    C C2 0.3892(2) 0.73841(11) 0.6956(3) 0.0389(5) Uani d . 1 1 . .
    C C3 0.4344(3) 0.83638(12) 0.7087(3) 0.0490(5) Uani d . 1 1 . .
    H H3 0.5811 0.8581 0.7432 0.059 Uiso d R 1 1 . .
    C C4 0.2677(3) 0.90140(12) 0.6715(3) 0.0519(6) Uani d . 1 1 . .
    H H4 0.2993 0.9692 0.6837 0.062 Uiso d R 1 1 . .
    C C5 0.0553(3) 0.87229(12) 0.6211(3) 0.0491(5) Uani d . 1 1 . .
    H H5 -0.0589 0.9190 0.5933 0.059 Uiso d R 1 1 . .
    C C6 0.0090(2) 0.77528(12) 0.6079(3) 0.0409(5) Uani d . 1 1 . .
    H H6 -0.1377 0.7535 0.5742 0.049 Uiso d R 1 1 . .
    C C7 0.1222(3) 0.60588(11) 0.6320(3) 0.0452(5) Uani d . 1 1 . .
    H H7 -0.0271 0.5880 0.6026 0.054 Uiso d R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0661(8) 0.0368(6) 0.0743(13) 0.0031(6) 0.0129(7) 0.0033(6)
    O2 0.0340(5) 0.0593(8) 0.0783(13) 0.0071(5) 0.0041(6) 0.0058(7)
    C1 0.0350(6) 0.0342(7) 0.0327(13) -0.0043(5) 0.0068(6) -0.0015(6)
    C2 0.0334(6) 0.0428(7) 0.0394(13) -0.0023(6) 0.0060(6) 0.0009(7)
    C3 0.0465(8) 0.0491(9) 0.0501(15) -0.0159(7) 0.0084(8) -0.0032(8)
    C4 0.0702(12) 0.0345(7) 0.0515(16) -0.0090(7) 0.0154(10) -0.0020(8)
    C5 0.0559(10) 0.0405(8) 0.0514(16) 0.0080(7) 0.0134(8) 0.0015(8)
    C6 0.0349(7) 0.0446(8) 0.0418(14) 0.0011(6) 0.0062(6) -0.0008(7)
    C7 0.0488(9) 0.0392(8) 0.0474(16) -0.0069(6) 0.0109(8) -0.0003(7)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.230(2) ?
    O2 C2 . 1.3499(19) ?
    O2 H2 . 1.0726 ?
    C1 C6 . 1.392(2) ?
    C1 C2 . 1.4075(19) ?
    C1 C7 . 1.449(2) ?
    C2 C3 . 1.390(2) ?
    C3 C4 . 1.375(3) ?
    C3 H3 . 0.9621 ?
    C4 C5 . 1.383(3) ?
    C4 H4 . 0.9637 ?
    C5 C6 . 1.378(2) ?
    C5 H5 . 0.9628 ?
    C6 H6 . 0.9620 ?
    C7 H7 . 0.9618 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O2 H2 . . 100.7 ?
    C6 C1 C2 . . 119.78(13) ?
    C6 C1 C7 . . 119.68(13) ?
    C2 C1 C7 . . 120.53(14) ?
    O2 C2 C3 . . 119.43(14) ?
    O2 C2 C1 . . 121.18(14) ?
    C3 C2 C1 . . 119.40(14) ?
    C4 C3 C2 . . 119.36(15) ?
    C4 C3 H3 . . 120.6 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 121.94(15) ?
    C3 C4 H4 . . 119.2 ?
    C5 C4 H4 . . 118.8 ?
    C6 C5 C4 . . 119.08(16) ?
    C6 C5 H5 . . 120.3 ?
    C4 C5 H5 . . 120.6 ?
    C5 C6 C1 . . 120.43(14) ?
    C5 C6 H6 . . 120.4 ?
    C1 C6 H6 . . 119.2 ?
    O1 C7 C1 . . 124.69(15) ?
    O1 C7 H7 . . 117.5 ?
    C1 C7 H7 . . 117.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 O2 . . . . -179.50(17) ?
    C7 C1 C2 O2 . . . . 0.6(3) ?
    C6 C1 C2 C3 . . . . 0.4(3) ?
    C7 C1 C2 C3 . . . . -179.50(19) ?
    O2 C2 C3 C4 . . . . 179.66(19) ?
    C1 C2 C3 C4 . . . . -0.2(3) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C3 C4 C5 C6 . . . . 0.1(3) ?
    C4 C5 C6 C1 . . . . 0.1(3) ?
    C2 C1 C6 C5 . . . . -0.3(3) ?
    C7 C1 C6 C5 . . . . 179.58(18) ?
    C6 C1 C7 O1 . . . . 179.85(19) ?
    C2 C1 C7 O1 . . . . -0.3(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O2 H2 O1 . 1.07 1.61 2.6231(18) 155.9
    C3 H3 O1 2_656 0.96 2.76 3.460(2) 129.9
    C7 H7 O1 3_566 0.96 2.73 3.443(2) 131.6
    C6 H6 O2 1_455 0.96 2.70 3.513(2) 142.6
_iucr_refine_instructions_details
;
TITL C7 H6 O2 in P2(1)/c
CELL 0.71073   6.3945  13.8939   6.9172  90.000 103.262  90.000
ZERR    4.00   0.0003   0.0009   0.0004   0.000   0.003   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H O
UNIT 28 24 8
ACTA 48
CONF
TEMP -40
OMIT    -1   2   2
OMIT    -2   6   5
OMIT    -1   6   5
OMIT    -3   5   5
OMIT    -2   5   3
EQIV $1 1-x, y+0.5, 1.5-z
EQIV $2 -x, 1-y, 1-z
EQIV $3 x-1, y, z
EQIV $4 x-1, 1.5-y, -0.5+z
HTAB O2 O1
HTAB C3 O1_$1
HTAB C7 O1_$2
HTAB C6 O2_$3
HTAB C6 O2_$4
MOVE 0.5 0 0 1
L.S. 8
BOND $H
FMAP 2
PLAN 10
REM   EXTI    0.000000
WGHT      0.1022      0.0000
FVAR       0.83042
O1    3   -0.244384    0.540613    0.661583    11.00000    0.06618    0.03681 =
         0.07429    0.00329    0.01295    0.00315
O2    3    0.052586    0.674534    0.731028    11.00000    0.03405    0.05942 =
         0.07833    0.00585    0.00412    0.00718
AFIX   3
H2    2   -0.034533    0.608011    0.705875    11.00000   -1.50000
AFIX   0
C1    1   -0.326174    0.707598    0.645120    11.00000    0.03506    0.03426 =
         0.03282   -0.00142    0.00687   -0.00427
C2    1   -0.110817    0.738418    0.695549    11.00000    0.03337    0.04282 =
         0.03940    0.00092    0.00595   -0.00224
C3    1   -0.065600    0.836374    0.708712    11.00000    0.04650    0.04918 =
         0.05008   -0.00319    0.00838   -0.01590
AFIX   3
H3    2    0.081110    0.858114    0.743233    11.00000   -1.20000
AFIX   0
C4    1   -0.232269    0.901394    0.671532    11.00000    0.07035    0.03451 =
         0.05164   -0.00204    0.01540   -0.00905
AFIX   3
H4    2   -0.200699    0.969244    0.683752    11.00000   -1.20000
AFIX   0
C5    1   -0.444649    0.872268    0.621077    11.00000    0.05590    0.04060 =
         0.05129    0.00153    0.01340    0.00812
AFIX   3
H5    2   -0.558829    0.918989    0.593338    11.00000   -1.20000
AFIX   0
C6    1   -0.490930    0.775281    0.607947    11.00000    0.03494    0.04480 =
         0.04172   -0.00085    0.00622    0.00112
AFIX   3
H6    2   -0.637629    0.753511    0.574157    11.00000   -1.20000
AFIX   0
C7    1   -0.377813    0.605894    0.631970    11.00000    0.04876    0.03931 =
         0.04755   -0.00029    0.01084   -0.00695
AFIX   3
H7    2   -0.527063    0.587974    0.602610    11.00000   -1.20000
HKLF 4
REM  C7 H6 O2 in P2(1)/c
REM R1 =  0.0573 for   1002 Fo > 4sig(Fo)  and  0.1095 for all   1853 data
REM     82 parameters refined using      0 restraints
END
REM Highest difference peak  0.315,  deepest hole -0.181,  1-sigma level  0.050
Q1    1  -0.3502  0.6569  0.6334  11.00000  0.05    0.31
Q2    1  -0.0858  0.7848  0.6814  11.00000  0.05    0.30
Q3    1  -0.4797  0.8268  0.6137  11.00000  0.05    0.25
Q4    1  -0.2200  0.7213  0.6797  11.00000  0.05    0.21
Q5    1   0.0478  0.6732  0.5025  11.00000  0.05    0.20
Q6    1  -0.2387  0.9693  0.8981  11.00000  0.05    0.19
Q7    1  -0.2591  0.9628  0.6321  11.00000  0.05    0.18
Q8    1  -0.2549  0.5422  0.9134  11.00000  0.05    0.18
Q9    1  -0.2178  0.9571  0.4836  11.00000  0.05    0.17
Q10   1  -0.3415  0.8915  0.6631  11.00000  0.05    0.17
;
data_III
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(2E)-3-phenylprop-2-enal
;
_chemical_name_common     'cinnamaldehyde'
_chemical_formula_moiety     'C9 H8 O'
_chemical_formula_sum     'C9 H8 O'
_chemical_formula_iupac     'C9 H8 O'
_chemical_formula_weight     132.15
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/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     5.9626(2)
_cell_length_b     12.9977(3)
_cell_length_c     9.2522(2)
_cell_angle_alpha     90.00
_cell_angle_beta     94.282(2)
_cell_angle_gamma     90.00
_cell_volume     715.04(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3800
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     31.15
_cell_measurement_temperature     173.0(10)
_exptl_crystal_description     cylinder
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.3
_exptl_crystal_size_min     0.3
_exptl_crystal_density_diffrn     1.228
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     .
_exptl_absorpt_correction_T_max     .
_exptl_special_details
;
The crystallization was performed on the diffractometer at a temperature of 248
K with a miniature zone melting procedure using focused infrared-laser-
radiation according to (Boese, 1994).
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
          'Siemens SMART three-axis goniometer with APEXII area-detector system'
_diffrn_measurement_method
                             'Data collection strategy APEX2/COSMO with chi = 0'
_diffrn_detector_area_resol_mean     512
_diffrn_reflns_number     7349
_diffrn_reflns_av_R_equivalents     0.0231
_diffrn_reflns_av_sigmaI/netI     0.0190
_diffrn_reflns_theta_min     2.71
_diffrn_reflns_theta_max     31.83
_diffrn_reflns_theta_full     24.00
_diffrn_measured_fraction_theta_max     0.725
_diffrn_measured_fraction_theta_full     0.893
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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. Treatment of hydrogen atoms Riding model on idealized geometrics
with the 1.2 fold isotropic displacement parameters of the equivalent
Uij of the corresponding carbon atom.
;
_reflns_number_total     1775
_reflns_number_gt     1648
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0542
_refine_ls_R_factor_gt     0.0498
_refine_ls_wR_factor_gt     0.1219
_refine_ls_wR_factor_ref     0.1250
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     1775
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0531P)²+0.1822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.275
_refine_diff_density_min     -0.170
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.014(9)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 [or SAINT?] (Bruker, 2006)'
_computing_structure_solution     'APEX2 (Bruker, 2006)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (Macrae et al., 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.0048(2) 0.36499(9) -0.40008(12) 0.0603(4) Uani d . 1 1 . .
    C C1 0.1694(3) 0.35814(9) -0.32532(14) 0.0415(4) Uani d . 1 1 . .
    H H1 0.3033 0.3424 -0.3726 0.050 Uiso d R 1 1 . .
    C C2 0.1944(2) 0.37243(9) -0.16888(13) 0.0375(3) Uani d . 1 1 . .
    H H2 0.0654 0.3899 -0.1177 0.045 Uiso d R 1 1 . .
    C C3 0.3937(2) 0.36146(8) -0.09649(12) 0.0331(3) Uani d . 1 1 . .
    H H3 0.5154 0.3430 -0.1536 0.040 Uiso d R 1 1 . .
    C C11 0.4498(2) 0.37396(8) 0.05945(12) 0.0315(3) Uani d . 1 1 . .
    C C12 0.2969(2) 0.41471(9) 0.15176(13) 0.0362(3) Uani d . 1 1 . .
    H H12 0.1499 0.4351 0.1128 0.043 Uiso d R 1 1 . .
    C C13 0.3560(3) 0.42581(10) 0.29890(14) 0.0413(4) Uani d . 1 1 . .
    H H13 0.2496 0.4537 0.3613 0.050 Uiso d R 1 1 . .
    C C14 0.5676(3) 0.39691(10) 0.35563(14) 0.0404(4) Uani d . 1 1 . .
    H H14 0.6060 0.4044 0.4577 0.048 Uiso d R 1 1 . .
    C C15 0.7210(2) 0.35616(10) 0.26582(14) 0.0393(3) Uani d . 1 1 . .
    H H15 0.8690 0.3370 0.3045 0.047 Uiso d R 1 1 . .
    C C16 0.6614(2) 0.34481(9) 0.11886(13) 0.0355(3) Uani d . 1 1 . .
    H H16 0.7666 0.3158 0.0566 0.043 Uiso d R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0558(9) 0.0722(7) 0.0496(6) -0.0015(5) -0.0178(6) -0.0016(5)
    C1 0.0460(11) 0.0380(6) 0.0396(6) -0.0018(5) -0.0021(6) -0.0014(5)
    C2 0.0351(10) 0.0402(6) 0.0370(6) -0.0001(5) 0.0011(6) -0.0008(4)
    C3 0.0333(9) 0.0299(5) 0.0360(6) 0.0008(4) 0.0030(5) -0.0009(4)
    C11 0.0303(9) 0.0282(5) 0.0360(5) -0.0027(4) 0.0024(5) 0.0007(4)
    C12 0.0303(9) 0.0382(6) 0.0400(6) 0.0008(5) 0.0021(5) -0.0017(4)
    C13 0.0397(10) 0.0460(6) 0.0389(6) -0.0034(5) 0.0074(6) -0.0053(5)
    C14 0.0424(10) 0.0433(6) 0.0352(6) -0.0074(5) 0.0005(6) 0.0016(5)
    C15 0.0324(9) 0.0425(6) 0.0420(6) -0.0029(5) -0.0031(6) 0.0059(5)
    C16 0.0298(9) 0.0367(6) 0.0402(6) 0.0005(5) 0.0034(5) 0.0017(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.2078(18) ?
    C1 C2 . 1.4559(17) ?
    C1 H1 . 0.9600 ?
    C2 C3 . 1.3270(19) ?
    C2 H2 . 0.9600 ?
    C3 C11 . 1.4656(16) ?
    C3 H3 . 0.9599 ?
    C11 C16 . 1.3907(19) ?
    C11 C12 . 1.3993(16) ?
    C12 C13 . 1.3881(18) ?
    C12 H12 . 0.9600 ?
    C13 C14 . 1.382(2) ?
    C13 H13 . 0.9600 ?
    C14 C15 . 1.3858(19) ?
    C14 H14 . 0.9600 ?
    C15 C16 . 1.3872(17) ?
    C15 H15 . 0.9600 ?
    C16 H16 . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 C2 . . 125.44(14) ?
    O1 C1 H1 . . 117.6 ?
    C2 C1 H1 . . 116.9 ?
    C3 C2 C1 . . 120.62(12) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.6 ?
    C2 C3 C11 . . 127.96(11) ?
    C2 C3 H3 . . 115.7 ?
    C11 C3 H3 . . 116.3 ?
    C16 C11 C12 . . 118.38(11) ?
    C16 C11 C3 . . 119.53(11) ?
    C12 C11 C3 . . 122.10(12) ?
    C13 C12 C11 . . 120.57(13) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.6 ?
    C14 C13 C12 . . 120.13(12) ?
    C14 C13 H13 . . 120.0 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C15 . . 120.05(12) ?
    C13 C14 H14 . . 119.3 ?
    C15 C14 H14 . . 120.6 ?
    C16 C15 C14 . . 119.75(13) ?
    C16 C15 H15 . . 119.9 ?
    C14 C15 H15 . . 120.4 ?
    C15 C16 C11 . . 121.11(11) ?
    C15 C16 H16 . . 120.0 ?
    C11 C16 H16 . . 118.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . 178.87(12) ?
    C1 C2 C3 C11 . . . . 179.26(10) ?
    C2 C3 C11 C16 . . . . 170.73(11) ?
    C2 C3 C11 C12 . . . . -9.36(18) ?
    C16 C11 C12 C13 . . . . 0.14(17) ?
    C3 C11 C12 C13 . . . . -179.77(11) ?
    C11 C12 C13 C14 . . . . 0.23(19) ?
    C12 C13 C14 C15 . . . . -0.40(19) ?
    C13 C14 C15 C16 . . . . 0.20(19) ?
    C14 C15 C16 C11 . . . . 0.18(18) ?
    C12 C11 C16 C15 . . . . -0.35(17) ?
    C3 C11 C16 C15 . . . . 179.57(10) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C13 H13 O1 3_565 0.96 2.81 3.5982(18) 140.0
    C14 H14 O1 1_656 0.96 2.63 3.304(2) 127.5
    C16 H16 O1 4_666 0.96 2.73 3.3880(17) 126.2
_iucr_refine_instructions_details
;
TITL C9 H8 O   in P2(1)/c at 173K
CELL 0.71073   5.9626  12.9977   9.2522  90.000  94.282  90.000
ZERR    4.00   0.0002   0.0003   0.0002   0.000   0.002   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H O
UNIT 36 32 4
TEMP -100.000
ACTA 48
OMIT     4   2   3
OMIT     2   5   7
OMIT     1   2   8
OMIT     0   2   4
OMIT     3   0   2
CONF
L.S. 8
BOND $H
EQIV $1 -x, 1-y, -z
EQIV $2 1+x, y, 1+z
EQIV $3 1+x, 0.5-y, 0.5+z
HTAB C13 O1_$1
HTAB C14 O1_$2
HTAB C16 O1_$3
FMAP 2
PLAN 10
WGHT      0.0531      0.1822
EXTI    0.011303
FVAR       1.33462
O1    3   -0.004788    0.364965   -0.400083    11.00000    0.05828    0.07164 =
         0.04877   -0.00127   -0.01700   -0.00151
C1    1    0.169555    0.358128   -0.325281    11.00000    0.04774    0.03773 =
         0.03873   -0.00130   -0.00183   -0.00177
AFIX   3
H1    2    0.303375    0.342398   -0.372531    11.00000   -1.20000
AFIX   0
C2    1    0.194436    0.372433   -0.168761    11.00000    0.03328    0.04058 =
         0.03682   -0.00078    0.00048   -0.00015
AFIX   3
H2    2    0.065426    0.389863   -0.117591    11.00000   -1.20000
AFIX   0
C3    1    0.393614    0.361485   -0.096514    11.00000    0.03196    0.03007 =
         0.03585   -0.00083    0.00251    0.00076
AFIX   3
H3    2    0.515344    0.342975   -0.153654    11.00000   -1.20000
AFIX   0
C11    1    0.450288    0.373975    0.059567    11.00000    0.03070    0.02804 =
         0.03570    0.00076    0.00271   -0.00265
C12    1    0.296453    0.414741    0.151575    11.00000    0.03141    0.03800 =
         0.03892   -0.00165    0.00244    0.00104
AFIX   3
H12    2    0.149463    0.435181    0.112595    11.00000   -1.20000
AFIX   0
C13    1    0.355908    0.425782    0.298937    11.00000    0.03845    0.04623 =
         0.03858   -0.00530    0.00682   -0.00339
AFIX   3
H13    2    0.249508    0.453662    0.361317    11.00000   -1.20000
AFIX   0
C14    1    0.567275    0.396912    0.355571    11.00000    0.04077    0.04354 =
         0.03475    0.00169   -0.00022   -0.00728
AFIX   3
H14    2    0.605625    0.404422    0.457651    11.00000   -1.20000
AFIX   0
C15    1    0.721216    0.356131    0.265858    11.00000    0.03418    0.04207 =
         0.04145    0.00598   -0.00229   -0.00268
AFIX   3
H15    2    0.869196    0.336931    0.304498    11.00000   -1.20000
AFIX   0
C16    1    0.661746    0.344813    0.118946    11.00000    0.02928    0.03667 =
         0.03992    0.00184    0.00316    0.00060
AFIX   3
H16    2    0.766866    0.315763    0.056646    11.00000   -1.20000
HKLF 4
REM  zimtaldehyd_100_0m in P2(1)/c
REM R1 =  0.0517 for   1653 Fo > 4sig(Fo)  and  0.0560 for all   1780 data
REM     92 parameters refined using      0 restraints
END
REM Highest difference peak  0.281,  deepest hole -0.193,  1-sigma level  0.034
Q1    1   0.1830  0.3616 -0.2425  11.00000  0.05    0.28
Q2    1   0.3554  0.4252  0.2254  11.00000  0.05    0.23
Q3    1   0.3577  0.3848  0.1094  11.00000  0.05    0.22
Q4    1   0.4058  0.3725 -0.0122  11.00000  0.05    0.22
Q5    1   0.6887  0.3674  0.1928  11.00000  0.05    0.21
Q6    1   0.6283  0.3731  0.3042  11.00000  0.05    0.19
Q7    1  -0.0733  0.3620 -0.3329  11.00000  0.05    0.16
Q8    1   0.4973  0.3385  0.1000  11.00000  0.05    0.13
Q9    1   0.5071  0.4306  0.3096  11.00000  0.05    0.11
Q10   1   0.3153  0.3995 -0.1280  11.00000  0.05    0.11
;
data_global
_journal_date_recd_electronic     2011-06-13
_journal_date_accepted     2011-09-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o387
_journal_page_last     o390
_journal_paper_category     FO
_journal_coeditor_code     FG3222
_publ_contact_author_name     'Roland Boese'
_publ_contact_author_address
;
Fachbereich Chemie der Universität Duisburg-Essen
Campus Essen
Universitätsstrasse 7
D-45117 Essen
Germany
;
_publ_contact_author_email     roland.boese@uni-due.de
_publ_contact_author_fax     '+49-201-1832535'
_publ_contact_author_phone     '+49-201-1832416'
_publ_section_title
;
Weak C---H...O hydrogen bonds in anisaldehyde, salicylaldehyde and
cinnamaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'Kirchner, Michael T.'
;
Faculty of Chemistry
University Duisburg--Essen
Universitätsstrasse 7
D-45117 Essen
Germany
;
    'Bläser, Dieter'
;
Faculty of Chemistry
University Duisburg--Essen
Universitätsstrasse 7
D-45117 Essen
Germany
;
    'Boese, Roland'
;
Faculty of Chemistry
University Duisburg--Essen
Universitätsstrasse 7
D-45117 Essen
Germany
;
    'Thakur, Tejender S.'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012
India
;
    'Desiraju, Gautam R.'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012
India
;
