# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'O-Pil Kwon'
_publ_contact_author_email       OPILKWON@AJOU.AC.KR

_publ_section_title              
;
Crystal engineering by eliminating weak hydrogen bonding
sites in phenolic polyene nonlinear optical crystals
;
loop_
_publ_author_name
'O-Pil Kwon'
'Peter Gunter'
'Mojca Jazbinsek'
'Seong-Ji Kwon'
'Yoon Sup Lee'
'Jung-In Seo'
;
J.-Y.Seo
;
'Hoseop Yun'

# Attachment 'OH3__CCDC-682357_.cif'

#==============================================================================

data_O-14
_database_code_depnum_ccdc_archive 'CCDC 682357'

_audit_update_record             
;
2009-03-10 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(3-(4-hydroxystyryl)cyclohex-2-enylidene)malononitrile
;
_chemical_name_common            
2-(3-(4-hydroxystyryl)cyclohex-2-enylidene)malononitrile
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0000 '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 0.0110 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'

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

_cell_length_a                   10.9927(8)
_cell_length_b                   12.5852(9)
_cell_length_c                   10.1326(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.364(2)
_cell_angle_gamma                90.00
_cell_volume                     1397.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)

_cell_measurement_reflns_used    5938
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      21.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;

;

_diffrn_ambient_temperature      290(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 R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6705
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1599
_reflns_number_gt                1411
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0824P)²+0.0284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         1599
_refine_ls_number_parameters     252
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37486(19) 0.7445(2) 0.9204(2) 0.0614(5) Uani 1 1 d . . .
C2 C 0.3593(2) 0.58795(19) 0.7812(2) 0.0651(5) Uani 1 1 d . . .
C3 C 0.33759(18) 0.69938(17) 0.79424(19) 0.0537(5) Uani 1 1 d . . .
C4 C 0.28951(16) 0.76123(17) 0.69193(18) 0.0476(4) Uani 1 1 d . . .
C5 C 0.25373(18) 0.71775(17) 0.56521(18) 0.0487(4) Uani 1 1 d . . .
C6 C 0.21059(19) 0.77700(15) 0.45921(19) 0.0474(4) Uani 1 1 d . . .
C7 C 0.18083(19) 0.72627(17) 0.33302(19) 0.0503(4) Uani 1 1 d . . .
C8 C 0.1345(2) 0.77491(16) 0.22290(19) 0.0507(4) Uani 1 1 d . . .
C9 C 0.10012(16) 0.72545(17) 0.09495(18) 0.0476(4) Uani 1 1 d . . .
C10 C 0.1119(2) 0.61662(17) 0.0721(2) 0.0581(5) Uani 1 1 d . . .
C11 C 0.0755(3) 0.57241(19) -0.0487(2) 0.0656(6) Uani 1 1 d . . .
C12 C 0.0258(2) 0.63605(17) -0.15174(19) 0.0549(5) Uani 1 1 d . . .
C13 C 0.01417(18) 0.74445(17) -0.13180(17) 0.0515(5) Uani 1 1 d . . .
C14 C 0.05024(18) 0.78790(16) -0.01024(18) 0.0502(4) Uani 1 1 d . . .
C15 C 0.2769(3) 0.87903(19) 0.7113(2) 0.0672(6) Uani 1 1 d . . .
C16A C 0.1902(6) 0.9277(3) 0.6162(4) 0.074(2) Uani 0.672(13) 1 d P . .
C16B C 0.2706(7) 0.9453(5) 0.5819(7) 0.053(3) Uani 0.328(13) 1 d P . .
C17 C 0.1970(3) 0.89512(17) 0.4733(2) 0.0647(6) Uani 1 1 d . . .
O1 O -0.0084(2) 0.58728(16) -0.26795(19) 0.0843(6) Uani 1 1 d . . .
N1 N 0.4057(3) 0.7810(2) 1.0207(2) 0.0814(6) Uani 1 1 d . . .
N2 N 0.3797(3) 0.4996(2) 0.7718(3) 0.0965(8) Uani 1 1 d . . .
H1 H -0.030(4) 0.626(3) -0.323(5) 0.103(12) Uiso 1 1 d . . .
H5 H 0.264(3) 0.639(3) 0.548(3) 0.080(9) Uiso 1 1 d . . .
H8 H 0.117(2) 0.854(2) 0.224(3) 0.059(6) Uiso 1 1 d . . .
H7 H 0.199(3) 0.654(3) 0.327(3) 0.065(7) Uiso 1 1 d . . .
H11 H 0.082(3) 0.499(3) -0.061(3) 0.082(8) Uiso 1 1 d . . .
H10 H 0.138(3) 0.567(2) 0.137(3) 0.065(7) Uiso 1 1 d . . .
H13 H -0.023(2) 0.787(2) -0.205(3) 0.062(7) Uiso 1 1 d . . .
H14 H 0.032(3) 0.860(3) 0.006(3) 0.073(8) Uiso 1 1 d . . .
H15A H 0.261(4) 0.889(4) 0.804(5) 0.119(13) Uiso 1 1 d . . .
H15B H 0.370(4) 0.908(4) 0.711(5) 0.122(14) Uiso 1 1 d . . .
H16A H 0.103(5) 0.906(4) 0.647(6) 0.090(15) Uiso 0.672(13) 1 d P . .
H16B H 0.360(7) 0.937(6) 0.550(8) 0.059(17) Uiso 0.328(13) 1 d P . .
H16C H 0.226(4) 1.007(3) 0.607(5) 0.106(10) Uiso 1 1 d . . .
H17A H 0.134(3) 0.924(3) 0.417(4) 0.084(9) Uiso 1 1 d . . .
H17B H 0.271(6) 0.929(5) 0.432(7) 0.16(2) Uiso 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.144(3) . ?
C1 C3 1.430(3) . ?
C2 N2 1.140(4) . ?
C2 C3 1.430(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.423(3) . ?
C4 C15 1.503(3) . ?
C5 C6 1.363(3) . ?
C5 H5 1.02(3) . ?
C6 C7 1.444(2) . ?
C6 C17 1.502(3) . ?
C7 C8 1.339(2) . ?
C7 H7 0.93(3) . ?
C8 C9 1.462(3) . ?
C8 H8 1.01(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.402(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.93(3) . ?
C11 C12 1.394(3) . ?
C11 H11 0.94(3) . ?
C12 O1 1.356(2) . ?
C12 C13 1.387(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.98(3) . ?
C14 H14 0.95(3) . ?
C15 C16A 1.440(5) . ?
C15 C16B 1.552(7) . ?
C15 H15A 0.97(5) . ?
C15 H15B 1.09(5) . ?
C16A C16B 0.999(8) . ?
C16A C17 1.512(5) . ?
C16A H16A 1.06(6) . ?
C16A H16C 1.08(4) . ?
C16B C17 1.458(7) . ?
C16B H16B 1.06(8) . ?
C16B H16C 0.96(4) . ?
C16B H17B 1.54(7) . ?
C17 H17A 0.94(4) . ?
C17 H17B 1.03(7) . ?
O1 H1 0.77(5) . ?

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
N1 C1 C3 179.3(3) . . ?
N2 C2 C3 178.2(3) . . ?
C4 C3 C1 121.26(18) . . ?
C4 C3 C2 123.01(18) . . ?
C1 C3 C2 115.67(19) . . ?
C3 C4 C5 121.90(18) . . ?
C3 C4 C15 119.71(18) . . ?
C5 C4 C15 118.37(18) . . ?
C6 C5 C4 123.80(17) . . ?
C6 C5 H5 116.0(19) . . ?
C4 C5 H5 120.2(19) . . ?
C5 C6 C7 119.85(16) . . ?
C5 C6 C17 119.85(18) . . ?
C7 C6 C17 120.28(18) . . ?
C8 C7 C6 125.58(16) . . ?
C8 C7 H7 117.3(19) . . ?
C6 C7 H7 117.0(19) . . ?
C7 C8 C9 126.92(16) . . ?
C7 C8 H8 120.3(16) . . ?
C9 C8 H8 112.8(16) . . ?
C10 C9 C14 117.36(18) . . ?
C10 C9 C8 122.93(18) . . ?
C14 C9 C8 119.69(17) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 114.0(18) . . ?
C9 C10 H10 124.5(17) . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 120(2) . . ?
C12 C11 H11 120(2) . . ?
O1 C12 C13 123.32(19) . . ?
O1 C12 C11 117.24(18) . . ?
C13 C12 C11 119.45(18) . . ?
C14 C13 C12 119.81(18) . . ?
C14 C13 H13 122.4(16) . . ?
C12 C13 H13 117.7(16) . . ?
C13 C14 C9 121.76(18) . . ?
C13 C14 H14 118.8(19) . . ?
C9 C14 H14 119.0(19) . . ?
C16A C15 C4 113.3(2) . . ?
C16A C15 C16B 38.8(3) . . ?
C4 C15 C16B 114.7(3) . . ?
C16A C15 H15A 116(3) . . ?
C4 C15 H15A 106(3) . . ?
C16B C15 H15A 138(3) . . ?
C16A C15 H15B 116(3) . . ?
C4 C15 H15B 103(2) . . ?
C16B C15 H15B 78(3) . . ?
H15A C15 H15B 101(4) . . ?
C16B C16A C15 76.7(5) . . ?
C16B C16A C17 67.5(5) . . ?
C15 C16A C17 116.6(3) . . ?
C16B C16A H16A 176(3) . . ?
C15 C16A H16A 105(3) . . ?
C17 C16A H16A 109(3) . . ?
C16B C16A H16C 55(2) . . ?
C15 C16A H16C 103(3) . . ?
C17 C16A H16C 97(3) . . ?
H16A C16A H16C 127(4) . . ?
C16A C16B C17 73.3(5) . . ?
C16A C16B C15 64.5(5) . . ?
C17 C16B C15 113.0(4) . . ?
C16A C16B H16B 161(4) . . ?
C17 C16B H16B 102(4) . . ?
C15 C16B H16B 103(4) . . ?
C16A C16B H16C 67(3) . . ?
C17 C16B H16C 107(3) . . ?
C15 C16B H16C 102(3) . . ?
H16B C16B H16C 131(5) . . ?
C16A C16B H17B 112(3) . . ?
C17 C16B H17B 40(2) . . ?
C15 C16B H17B 139(2) . . ?
H16B C16B H17B 68(5) . . ?
H16C C16B H17B 114(4) . . ?
C16B C17 C6 116.6(3) . . ?
C16B C17 C16A 39.3(3) . . ?
C6 C17 C16A 111.8(2) . . ?
C16B C17 H17A 129(2) . . ?
C6 C17 H17A 114(2) . . ?
C16A C17 H17A 113(2) . . ?
C16B C17 H17B 74(4) . . ?
C6 C17 H17B 106(4) . . ?
C16A C17 H17B 112(4) . . ?
H17A C17 H17B 99(4) . . ?
C12 O1 H1 113(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.033


