# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Len MacGillivray'
_publ_contact_author_email       LEN-MACGILLIVRAY@UIOWA.EDU

_publ_section_title              
;
ineering cocrystal and polymorph architecture via
pseudoseeding
;
loop_
_publ_author_name
'Len MacGillivray'
'Tomislav Friscic'

# Attachment 'deposit1.cif'

data_(RES).(4,4'-BPE)
_database_code_depnum_ccdc_archive 'CCDC 707408'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
resorcinol . trans-1,2-bis(4-pyridyl)ethylene 1/2 form 2
;
_chemical_name_common            
'resorcinol . trans-1,2-bis(4-pyridyl)ethylene 1/2 form 2'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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   P21/n

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                   10.1465(10)
_cell_length_b                   7.1871(7)
_cell_length_c                   20.042(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.797(5)
_cell_angle_gamma                90.00
_cell_volume                     1456.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    5565
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10675
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3342
_reflns_number_gt                2314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_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^)+(0.0620P)^2^+0.2458P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3342
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
O1 O 0.93157(11) 0.62071(16) 0.55378(5) 0.0367(3) Uani 1 1 d . . .
H1 H 1.0081 0.6658 0.5547 0.055 Uiso 1 1 calc R . .
O2 O 0.54331(10) 0.64940(17) 0.66535(5) 0.0365(3) Uani 1 1 d . . .
H2 H 0.5158 0.6725 0.7029 0.055 Uiso 1 1 calc R . .
N1 N 1.17087(13) 0.78252(19) 0.53137(7) 0.0359(4) Uani 1 1 d . . .
N2 N 1.90742(13) 0.80203(18) 0.27599(6) 0.0306(3) Uani 1 1 d . . .
C1 C 1.15543(16) 0.8645(2) 0.47144(8) 0.0351(4) Uani 1 1 d . . .
H1A H 1.0700 0.9093 0.4564 0.042 Uiso 1 1 calc R . .
C2 C 1.25633(16) 0.8879(2) 0.42998(8) 0.0322(4) Uani 1 1 d . . .
H2A H 1.2393 0.9460 0.3876 0.039 Uiso 1 1 calc R . .
C3 C 1.38310(15) 0.8260(2) 0.45078(7) 0.0270(3) Uani 1 1 d . . .
C4 C 1.40052(15) 0.7460(2) 0.51444(8) 0.0311(4) Uani 1 1 d . . .
H4 H 1.4856 0.7049 0.5318 0.037 Uiso 1 1 calc R . .
C5 C 1.29377(16) 0.7271(2) 0.55186(8) 0.0340(4) Uani 1 1 d . . .
H5 H 1.3080 0.6713 0.5948 0.041 Uiso 1 1 calc R . .
C6 C 1.48813(15) 0.8438(2) 0.40523(8) 0.0304(4) Uani 1 1 d . . .
H6 H 1.4646 0.9011 0.3632 0.036 Uiso 1 1 calc R . .
C7 C 1.61244(16) 0.7883(2) 0.41650(8) 0.0301(4) Uani 1 1 d . . .
H7 H 1.6383 0.7370 0.4593 0.036 Uiso 1 1 calc R . .
C8 C 1.71357(15) 0.7994(2) 0.36855(7) 0.0272(3) Uani 1 1 d . . .
C9 C 1.69199(16) 0.8870(2) 0.30627(8) 0.0330(4) Uani 1 1 d . . .
H9 H 1.6104 0.9478 0.2941 0.040 Uiso 1 1 calc R . .
C10 C 1.78984(16) 0.8842(2) 0.26286(8) 0.0336(4) Uani 1 1 d . . .
H10 H 1.7729 0.9445 0.2208 0.040 Uiso 1 1 calc R . .
C11 C 1.83691(15) 0.7178(2) 0.38301(8) 0.0302(4) Uani 1 1 d . . .
H11 H 1.8578 0.6597 0.4251 0.036 Uiso 1 1 calc R . .
C12 C 1.92905(15) 0.7214(2) 0.33612(8) 0.0307(4) Uani 1 1 d . . .
H12 H 2.0122 0.6636 0.3471 0.037 Uiso 1 1 calc R . .
C13 C 0.87414(15) 0.6729(2) 0.61015(7) 0.0268(3) Uani 1 1 d . . .
C14 C 0.74121(14) 0.6320(2) 0.61256(7) 0.0268(3) Uani 1 1 d . . .
H14 H 0.6950 0.5669 0.5766 0.032 Uiso 1 1 calc R . .
C15 C 0.67528(15) 0.6861(2) 0.66745(7) 0.0271(4) Uani 1 1 d . . .
C16 C 0.74410(16) 0.7756(2) 0.72111(8) 0.0321(4) Uani 1 1 d . . .
H16 H 0.7001 0.8120 0.7590 0.039 Uiso 1 1 calc R . .
C17 C 0.87771(16) 0.8109(2) 0.71850(8) 0.0344(4) Uani 1 1 d . . .
H17 H 0.9252 0.8701 0.7555 0.041 Uiso 1 1 calc R . .
C18 C 0.94389(15) 0.7623(2) 0.66353(8) 0.0318(4) Uani 1 1 d . . .
H18 H 1.0353 0.7895 0.6623 0.038 Uiso 1 1 calc R . .

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
O1 0.0274(6) 0.0507(7) 0.0334(6) -0.0062(5) 0.0111(5) -0.0017(5)
O2 0.0249(6) 0.0555(7) 0.0305(6) 0.0003(6) 0.0099(5) -0.0033(5)
N1 0.0299(8) 0.0451(8) 0.0339(8) -0.0045(7) 0.0099(6) -0.0044(6)
N2 0.0276(7) 0.0337(7) 0.0316(7) -0.0013(6) 0.0084(6) -0.0014(6)
C1 0.0253(9) 0.0423(9) 0.0386(9) -0.0008(8) 0.0069(7) 0.0029(7)
C2 0.0321(9) 0.0336(9) 0.0315(8) 0.0022(7) 0.0067(7) 0.0016(7)
C3 0.0267(8) 0.0264(7) 0.0287(8) -0.0035(6) 0.0067(6) -0.0017(6)
C4 0.0264(8) 0.0377(9) 0.0295(8) -0.0003(7) 0.0043(7) -0.0004(7)
C5 0.0326(9) 0.0428(9) 0.0277(8) 0.0008(7) 0.0084(7) -0.0050(7)
C6 0.0297(9) 0.0353(8) 0.0272(8) 0.0023(7) 0.0081(6) 0.0006(7)
C7 0.0320(9) 0.0331(8) 0.0263(8) 0.0022(7) 0.0088(7) 0.0005(7)
C8 0.0265(8) 0.0287(8) 0.0271(8) -0.0017(6) 0.0067(6) -0.0012(6)
C9 0.0274(9) 0.0390(9) 0.0334(9) 0.0071(7) 0.0081(7) 0.0062(7)
C10 0.0335(9) 0.0397(9) 0.0286(8) 0.0068(7) 0.0089(7) 0.0027(7)
C11 0.0280(9) 0.0359(9) 0.0269(8) 0.0025(7) 0.0024(7) 0.0006(7)
C12 0.0228(8) 0.0354(9) 0.0342(9) -0.0001(7) 0.0041(7) 0.0014(6)
C13 0.0252(8) 0.0291(8) 0.0270(8) 0.0021(6) 0.0068(6) 0.0028(6)
C14 0.0256(8) 0.0299(8) 0.0249(8) 0.0004(6) 0.0027(6) -0.0008(6)
C15 0.0231(8) 0.0306(8) 0.0283(8) 0.0050(7) 0.0068(6) -0.0001(6)
C16 0.0348(9) 0.0360(9) 0.0267(8) -0.0020(7) 0.0094(7) -0.0011(7)
C17 0.0341(9) 0.0387(9) 0.0301(9) -0.0046(7) 0.0007(7) -0.0041(7)
C18 0.0227(8) 0.0365(9) 0.0365(9) -0.0011(7) 0.0042(7) -0.0022(7)

_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
O1 C13 1.3662(18) . ?
O2 C15 1.3620(17) . ?
N1 C1 1.335(2) . ?
N1 C5 1.340(2) . ?
N2 C10 1.337(2) . ?
N2 C12 1.339(2) . ?
C1 C2 1.382(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.397(2) . ?
C3 C6 1.466(2) . ?
C4 C5 1.375(2) . ?
C6 C7 1.324(2) . ?
C7 C8 1.466(2) . ?
C8 C11 1.390(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.374(2) . ?
C11 C12 1.380(2) . ?
C13 C14 1.385(2) . ?
C13 C18 1.390(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.382(2) . ?

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
C1 N1 C5 116.29(14) . . ?
C10 N2 C12 116.40(13) . . ?
N1 C1 C2 123.89(15) . . ?
C1 C2 C3 119.58(15) . . ?
C2 C3 C4 116.64(14) . . ?
C2 C3 C6 119.18(14) . . ?
C4 C3 C6 124.17(14) . . ?
C5 C4 C3 119.57(15) . . ?
N1 C5 C4 123.97(15) . . ?
C7 C6 C3 126.83(15) . . ?
C6 C7 C8 125.52(15) . . ?
C11 C8 C9 116.53(14) . . ?
C11 C8 C7 120.52(14) . . ?
C9 C8 C7 122.94(14) . . ?
C10 C9 C8 119.42(15) . . ?
N2 C10 C9 124.17(15) . . ?
C12 C11 C8 119.96(14) . . ?
N2 C12 C11 123.48(14) . . ?
O1 C13 C14 117.04(13) . . ?
O1 C13 C18 122.58(14) . . ?
C14 C13 C18 120.38(14) . . ?
C13 C14 C15 120.19(14) . . ?
O2 C15 C14 117.28(13) . . ?
O2 C15 C16 122.85(14) . . ?
C14 C15 C16 119.86(14) . . ?
C17 C16 C15 119.05(15) . . ?
C18 C17 C16 121.76(15) . . ?
C17 C18 C13 118.71(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
C5 N1 C1 C2 2.3(2) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C6 177.24(14) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C6 C3 C4 C5 -176.57(15) . . . . ?
C1 N1 C5 C4 -1.6(2) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C2 C3 C6 C7 -178.33(15) . . . . ?
C4 C3 C6 C7 0.2(3) . . . . ?
C3 C6 C7 C8 176.64(14) . . . . ?
C6 C7 C8 C11 -172.69(16) . . . . ?
C6 C7 C8 C9 6.0(3) . . . . ?
C11 C8 C9 C10 1.6(2) . . . . ?
C7 C8 C9 C10 -177.09(15) . . . . ?
C12 N2 C10 C9 -1.2(2) . . . . ?
C8 C9 C10 N2 -0.1(3) . . . . ?
C9 C8 C11 C12 -1.9(2) . . . . ?
C7 C8 C11 C12 176.86(14) . . . . ?
C10 N2 C12 C11 0.9(2) . . . . ?
C8 C11 C12 N2 0.6(2) . . . . ?
O1 C13 C14 C15 -178.00(13) . . . . ?
C18 C13 C14 C15 2.3(2) . . . . ?
C13 C14 C15 O2 177.04(13) . . . . ?
C13 C14 C15 C16 -2.3(2) . . . . ?
O2 C15 C16 C17 -178.68(14) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C16 C17 C18 C13 -1.1(2) . . . . ?
O1 C13 C18 C17 179.70(14) . . . . ?
C14 C13 C18 C17 -0.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.052