Electronic Supplementary Material for CrystEngComm
This journal is (c) the Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'R. Glaser'
_publ_contact_author_address     
;
Department of Chemistry
University of Missouri
Columbia
Missouri
65211
UNITED STATES OF AMERICA
;

_publ_contact_author_email       GLASERR@MISSOURI.EDU

_publ_section_title              
;
Crystal structure of 4-chlorobenzaldazine:
Ph-Cl...H?CPh=N?R' contacts and their relation to idioteloamphiphile
layer architecture
;
loop_
_publ_author_name
'R. Glaser'
'Charles L. Barnes'
'Sung Hoon Kim.'
'Richard F. Murphy'
'Yongqiang Sui.'

# Attachment 'CBA_SI.cif'

data_4-Chlorobenzaldazine
_database_code_depnum_ccdc_archive 'CCDC 292918'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E,E)-1,2-bis-4-chlorobenzaldazine
;
_chemical_name_common            (E,E)-1,2-bis-4-chlorobenzaldazine
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl2 N2'
_chemical_formula_sum            'C14 H10 Cl2 N2'
_chemical_formula_weight         277.14

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2~1~/c

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                   3.8917(5)
_cell_length_b                   6.9999(8)
_cell_length_c                   22.977(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.798(2)
_cell_angle_gamma                90.00
_cell_volume                     625.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3427
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.1

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   
;
Data were corrected for decay and absorption using the program SADABS
based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995).
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            4248
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.12
_reflns_number_total             1367
_reflns_number_gt                1281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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^)+(0.0514P)^2^+0.1458P] 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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1367
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.89903(9) 1.33329(5) 0.687598(16) 0.04100(16) Uani 1 1 d . . .
N1 N 0.5608(3) 0.58903(15) 0.51029(5) 0.0314(3) Uani 1 1 d . . .
C1 C 0.4850(3) 0.61641(19) 0.56355(6) 0.0298(3) Uani 1 1 d . . .
H1 H 0.3622 0.5208 0.5840 0.036 Uiso 1 1 calc R . .
C2 C 0.5844(3) 0.79287(18) 0.59362(5) 0.0273(3) Uani 1 1 d . . .
C3 C 0.5180(3) 0.81548(19) 0.65269(6) 0.0307(3) Uani 1 1 d . . .
H3 H 0.4066 0.7160 0.6733 0.037 Uiso 1 1 calc R . .
C4 C 0.6125(3) 0.9814(2) 0.68179(6) 0.0313(3) Uani 1 1 d . . .
H4 H 0.5675 0.9961 0.7221 0.038 Uiso 1 1 calc R . .
C5 C 0.7734(3) 1.12528(19) 0.65106(6) 0.0285(3) Uani 1 1 d . . .
C6 C 0.8395(3) 1.10895(19) 0.59214(6) 0.0299(3) Uani 1 1 d . . .
H6 H 0.9473 1.2099 0.5716 0.036 Uiso 1 1 calc R . .
C7 C 0.7444(3) 0.94197(19) 0.56393(5) 0.0287(3) Uani 1 1 d . . .
H7 H 0.7888 0.9284 0.5236 0.034 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
Cl1 0.0398(2) 0.0397(2) 0.0436(2) -0.01678(14) 0.00290(16) -0.00497(13)
N1 0.0346(6) 0.0263(6) 0.0332(6) -0.0026(4) -0.0010(4) -0.0051(5)
C1 0.0288(6) 0.0279(6) 0.0326(6) 0.0010(5) 0.0001(5) -0.0029(5)
C2 0.0241(6) 0.0276(6) 0.0301(6) -0.0002(5) -0.0009(5) 0.0007(5)
C3 0.0316(7) 0.0312(6) 0.0293(6) 0.0044(5) 0.0027(5) -0.0014(5)
C4 0.0315(7) 0.0377(7) 0.0248(6) -0.0010(5) 0.0008(5) 0.0030(5)
C5 0.0242(6) 0.0297(6) 0.0317(6) -0.0064(5) -0.0019(5) 0.0017(5)
C6 0.0293(6) 0.0283(6) 0.0323(7) -0.0004(5) 0.0026(5) -0.0033(5)
C7 0.0293(6) 0.0320(7) 0.0249(6) -0.0013(5) 0.0024(5) -0.0021(5)

_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
Cl1 C5 1.7471(13) . ?
N1 C1 1.2772(18) . ?
N1 N1 1.412(2) 3_666 ?
C1 C2 1.4648(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3943(18) . ?
C2 C7 1.3979(19) . ?
C3 C4 1.3873(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3862(18) . ?
C6 C7 1.3844(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?

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 N1 111.86(14) . 3_666 ?
N1 C1 C2 121.02(12) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C7 118.70(12) . . ?
C3 C2 C1 120.23(12) . . ?
C7 C2 C1 121.06(11) . . ?
C4 C3 C2 120.84(12) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.82(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.96(12) . . ?
C4 C5 Cl1 119.13(10) . . ?
C6 C5 Cl1 118.92(11) . . ?
C7 C6 C5 118.36(12) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C2 121.32(11) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?

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
N1 N1 C1 C2 -179.56(12) 3_666 . . . ?
N1 C1 C2 C3 -176.09(13) . . . . ?
N1 C1 C2 C7 4.4(2) . . . . ?
C7 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C4 179.65(12) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 Cl1 -179.06(10) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
Cl1 C5 C6 C7 178.82(10) . . . . ?
C5 C6 C7 C2 0.3(2) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C1 C2 C7 C6 -179.89(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.065


