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### ###
### Electronic paper (Acta Crystallographica Section E) ###
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# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, 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. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
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data_global
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2009-02-09
_journal_date_accepted 2009-02-10
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2009
_journal_volume 65
_journal_issue 3
_journal_page_first o553
_journal_page_last o553
_journal_paper_category QO
_journal_coeditor_code NG2544
_publ_contact_author_name 'Simpson, Jim'
_publ_contact_author_address
;
Department of Chemistry,
University of Otago
PO Box 56,
Dunedin, 9054
New Zealand
;
_publ_contact_author_email jsimpson@alkali.otago.ac.nz
_publ_contact_author_fax 6434797906
_publ_contact_author_phone 6434797914
_publ_section_title
;
(E)-4-Bromo-N-(2,4-dimethoxybenzylidene)aniline
;
loop_
_publ_author_name
_publ_author_address
'Khalaji, Aliakbar D.'
;
Department of Chemistry
Faculty of Science
Golestan University
Gorgan
Iran
;
'Simpson, Jim'
;
Department of Chemistry
University of Otago
PO Box 56
Dunedin
New Zealand
;
data_I
_chemical_name_systematic
;
(E)-4-Bromo-N-(2,4-dimethoxybenzylidene)aniline
;
_chemical_name_common ?
_chemical_formula_moiety 'C15 H14 Br N O2'
_chemical_formula_sum 'C15 H14 Br N O2'
_chemical_formula_iupac 'C15 H14 Br N O2'
_chemical_formula_weight 320.18
_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 4.1323(6)
_cell_length_b 10.7406(14)
_cell_length_c 29.911(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.992(8)
_cell_angle_gamma 90.00
_cell_volume 1327.4(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 2351
_cell_measurement_theta_min 2.72
_cell_measurement_theta_max 23.60
_cell_measurement_temperature 89(2)
_exptl_crystal_description 'rectangular plate'
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.02
_exptl_crystal_density_diffrn 1.602
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 648
_exptl_absorpt_coefficient_mu 3.094
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2006)'
_exptl_absorpt_correction_T_min 0.570
_exptl_absorpt_correction_T_max 0.940
_exptl_special_details
;
;
_diffrn_ambient_temperature 89(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 'Bruker APEXII CCD area-detector'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 13728
_diffrn_reflns_av_R_equivalents 0.1057
_diffrn_reflns_av_sigmaI/netI 0.0735
_diffrn_reflns_theta_min 2.01
_diffrn_reflns_theta_max 25.29
_diffrn_reflns_theta_full 25.29
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -3
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_limit_l_max 35
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_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^ >
\s(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.
;
_reflns_number_total 2390
_reflns_number_gt 1664
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0894
_refine_ls_R_factor_gt 0.0560
_refine_ls_wR_factor_gt 0.1102
_refine_ls_wR_factor_ref 0.1183
_refine_ls_goodness_of_fit_ref 1.206
_refine_ls_restrained_S_all 1.206
_refine_ls_number_reflns 2390
_refine_ls_number_parameters 174
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0212P)^2^+3P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max ?
_refine_ls_shift/su_max_lt 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.834
_refine_diff_density_min -0.819
_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'
'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'
'Br' 'Br' -0.2901 2.4595
'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) and SAINT (Bruker, 2006)'
_computing_data_reduction 'SAINT (Bruker, 2006)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,
2004), PLATON (Spek, 2009)
and publCIF (Westrip, 2009)
;
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_disorder_assembly
_atom_site_disorder_group
N N1 0.8952(10) 0.5770(4) 0.37825(15) 0.0157(10) Uani d . 1 . .
C C1 0.7282(12) 0.6745(5) 0.38778(18) 0.0154(12) Uani d . 1 . .
H H1 0.6759 0.7321 0.3647 0.018 Uiso calc R 1 . .
C C2 0.6171(12) 0.6989(5) 0.43302(17) 0.0138(12) Uani d . 1 . .
C C3 0.4148(12) 0.8016(5) 0.44237(18) 0.0133(12) Uani d . 1 . .
O O1 0.3071(9) 0.8689(3) 0.40592(12) 0.0174(9) Uani d . 1 . .
C C4 0.1171(13) 0.9771(4) 0.41475(18) 0.0159(12) Uani d . 1 . .
H H4A -0.0826 0.9525 0.4296 0.024 Uiso calc R 1 . .
H H4B 0.0632 1.0192 0.3865 0.024 Uiso calc R 1 . .
H H4C 0.2406 1.0339 0.4342 0.024 Uiso calc R 1 . .
C C5 0.3327(12) 0.8293(5) 0.48586(18) 0.0155(12) Uani d . 1 . .
H H5 0.2003 0.8994 0.4919 0.019 Uiso calc R 1 . .
C C6 0.4459(12) 0.7535(5) 0.52094(17) 0.0138(12) Uani d . 1 . .
O O2 0.3510(9) 0.7888(3) 0.56290(11) 0.0167(9) Uani d . 1 . .
C C7 0.4941(14) 0.7232(5) 0.59995(18) 0.0222(13) Uani d . 1 . .
H H7A 0.4270 0.6357 0.5989 0.033 Uiso calc R 1 . .
H H7B 0.4228 0.7607 0.6280 0.033 Uiso calc R 1 . .
H H7C 0.7304 0.7283 0.5984 0.033 Uiso calc R 1 . .
C C8 0.6428(12) 0.6515(5) 0.51264(17) 0.0153(12) Uani d . 1 . .
H H8 0.7184 0.5999 0.5364 0.018 Uiso calc R 1 . .
C C9 0.7263(12) 0.6267(5) 0.46874(18) 0.0160(12) Uani d . 1 . .
H H9 0.8634 0.5578 0.4629 0.019 Uiso calc R 1 . .
C C10 1.0177(13) 0.5654(6) 0.33449(18) 0.0169(13) Uani d . 1 . .
C C11 1.1201(12) 0.6657(5) 0.30882(18) 0.0181(13) Uani d . 1 . .
H H11 1.0997 0.7481 0.3200 0.022 Uiso calc R 1 . .
C C12 1.2516(13) 0.6466(5) 0.26700(18) 0.0179(12) Uani d . 1 . .
H H12 1.3267 0.7153 0.2501 0.022 Uiso calc R 1 . .
C C13 1.2726(12) 0.5278(5) 0.25015(18) 0.0164(13) Uani d . 1 . .
Br Br1 1.44896(13) 0.49899(7) 0.192736(17) 0.02466(19) Uani d . 1 . .
C C14 1.1702(12) 0.4254(5) 0.27488(19) 0.0172(12) Uani d . 1 . .
H H14 1.1866 0.3432 0.2633 0.021 Uiso calc R 1 . .
C C15 1.0447(13) 0.4469(6) 0.31650(18) 0.0176(13) Uani d . 1 . .
H H15 0.9738 0.3779 0.3336 0.021 Uiso calc R 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
N1 0.018(2) 0.013(3) 0.017(2) 0.000(2) 0.004(2) -0.0016(19)
C1 0.018(3) 0.011(3) 0.017(3) -0.005(2) 0.002(2) -0.003(2)
C2 0.014(3) 0.009(3) 0.018(3) -0.001(2) 0.003(2) -0.002(2)
C3 0.008(3) 0.013(3) 0.019(3) 0.000(2) 0.001(2) -0.003(2)
O1 0.020(2) 0.016(2) 0.016(2) 0.0038(17) 0.0036(16) -0.0012(16)
C4 0.022(3) 0.006(3) 0.021(3) 0.001(2) 0.002(2) 0.002(2)
C5 0.015(3) 0.008(3) 0.024(3) -0.003(2) 0.003(2) -0.003(2)
C6 0.016(3) 0.012(3) 0.014(3) -0.006(2) 0.002(2) -0.002(2)
O2 0.023(2) 0.015(2) 0.012(2) -0.0021(17) 0.0038(16) -0.0013(16)
C7 0.036(3) 0.015(3) 0.015(3) -0.001(3) 0.004(3) 0.000(2)
C8 0.017(3) 0.016(3) 0.013(3) -0.002(2) 0.003(2) 0.006(2)
C9 0.014(3) 0.012(3) 0.022(3) -0.003(2) 0.001(2) -0.003(2)
C10 0.017(3) 0.020(3) 0.014(3) 0.003(2) 0.003(2) -0.005(2)
C11 0.018(3) 0.012(3) 0.024(3) 0.002(2) 0.003(2) -0.002(2)
C12 0.018(3) 0.014(3) 0.022(3) -0.003(2) 0.007(2) 0.002(2)
C13 0.014(3) 0.020(4) 0.016(3) 0.002(2) 0.006(2) -0.005(2)
Br1 0.0271(3) 0.0313(3) 0.0159(3) 0.0036(3) 0.0069(2) -0.0002(3)
C14 0.020(3) 0.009(3) 0.022(3) 0.002(2) 0.005(2) -0.002(2)
C15 0.022(3) 0.016(3) 0.014(3) -0.005(2) 0.000(3) 0.003(2)
_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
N1 C1 . 1.288(7) ?
N1 C10 . 1.417(7) ?
C1 C2 . 1.460(7) ?
C1 H1 . 0.9500 ?
C2 C9 . 1.389(7) ?
C2 C3 . 1.415(7) ?
C3 O1 . 1.376(6) ?
C3 C5 . 1.383(7) ?
O1 C4 . 1.430(6) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 C6 . 1.402(7) ?
C5 H5 . 0.9500 ?
C6 O2 . 1.375(6) ?
C6 C8 . 1.390(7) ?
O2 C7 . 1.432(6) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.389(7) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C15 . 1.387(8) ?
C10 C11 . 1.393(8) ?
C11 C12 . 1.388(7) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.375(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.396(7) ?
C13 Br1 . 1.902(5) ?
C14 C15 . 1.376(8) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
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
C1 N1 C10 . . 118.5(5) ?
N1 C1 C2 . . 122.0(5) ?
N1 C1 H1 . . 119.0 ?
C2 C1 H1 . . 119.0 ?
C9 C2 C3 . . 117.9(5) ?
C9 C2 C1 . . 120.6(5) ?
C3 C2 C1 . . 121.3(5) ?
O1 C3 C5 . . 123.4(5) ?
O1 C3 C2 . . 115.9(4) ?
C5 C3 C2 . . 120.6(5) ?
C3 O1 C4 . . 116.9(4) ?
O1 C4 H4A . . 109.5 ?
O1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
O1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 C6 . . 119.7(5) ?
C3 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
O2 C6 C8 . . 123.9(5) ?
O2 C6 C5 . . 115.2(5) ?
C8 C6 C5 . . 120.9(5) ?
C6 O2 C7 . . 116.8(4) ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C6 C8 C9 . . 118.4(5) ?
C6 C8 H8 . . 120.8 ?
C9 C8 H8 . . 120.8 ?
C2 C9 C8 . . 122.5(5) ?
C2 C9 H9 . . 118.7 ?
C8 C9 H9 . . 118.7 ?
C15 C10 C11 . . 117.9(5) ?
C15 C10 N1 . . 118.1(5) ?
C11 C10 N1 . . 123.9(5) ?
C12 C11 C10 . . 120.6(5) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.7(5) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 121.0(5) ?
C12 C13 Br1 . . 120.6(4) ?
C14 C13 Br1 . . 118.3(4) ?
C15 C14 C13 . . 118.0(5) ?
C15 C14 H14 . . 121.0 ?
C13 C14 H14 . . 121.0 ?
C14 C15 C10 . . 122.6(5) ?
C14 C15 H15 . . 118.7 ?
C10 C15 H15 . . 118.7 ?
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
C7 H7A N1 3_666 0.98 2.74 3.667(7) 158.5
C4 H4C O2 3_676 0.98 2.54 3.398(6) 145.4