#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/93/2219331.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2219331
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Mirkhani, Valiollah'
'Vartooni, Akbar Rostami'
_publ_section_title
;
 N,N'-Bis(3-methoxybenzylidene)ethane-1,2-diamine
;
_journal_coeditor_code           FL2216
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1803
_journal_page_last               o1804
_journal_paper_doi               10.1107/S1600536808026652
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H20 N2 O2'
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_chemical_name_systematic
;
N,N'-Bis(3-methoxybenzylidene)ethane-1,2-diamine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.7076(3)
_cell_length_b                   6.03740(10)
_cell_length_c                   11.6789(2)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.88
_cell_measurement_theta_min      3.55
_cell_volume                     1575.64(4)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11683
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0467P)²+0.7792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1879
_reflns_number_total             2298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2216.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2219331
_cod_database_fobs_code          2219331
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O O1 0.29856(3) 0.12810(12) 0.16829(6) 0.02029(18) Uani d . 1
N N1 0.44163(4) 0.77578(14) 0.17093(8) 0.0197(2) Uani d . 1
C C1 0.36408(4) 0.39310(16) 0.11788(8) 0.0166(2) Uani d . 1
H H1A 0.3629 0.4625 0.1885 0.020 Uiso calc R 1
C C2 0.33032(4) 0.20304(16) 0.08715(8) 0.0167(2) Uani d . 1
C C3 0.33099(4) 0.10022(17) -0.01966(9) 0.0196(2) Uani d . 1
H H3A 0.3080 -0.0257 -0.0407 0.024 Uiso calc R 1
C C4 0.36637(4) 0.18805(18) -0.09415(9) 0.0216(2) Uani d . 1
H H4A 0.3671 0.1197 -0.1653 0.026 Uiso calc R 1
C C5 0.40051(4) 0.37574(18) -0.06388(9) 0.0203(2) Uani d . 1
H H5A 0.4240 0.4328 -0.1145 0.024 Uiso calc R 1
C C6 0.39970(4) 0.47980(17) 0.04289(8) 0.0172(2) Uani d . 1
C C7 0.43794(4) 0.67504(17) 0.07480(9) 0.0184(2) Uani d . 1
C C8 0.48159(5) 0.96685(17) 0.18898(10) 0.0215(2) Uani d . 1
C C9 0.26352(5) -0.06749(17) 0.14119(10) 0.0225(2) Uani d . 1
H H9A 0.2443 -0.1047 0.2055 0.034 Uiso calc R 1
H H9B 0.2890 -0.1874 0.1267 0.034 Uiso calc R 1
H H9C 0.2337 -0.0419 0.0731 0.034 Uiso calc R 1
H H7A 0.4614(6) 0.722(2) 0.0143(11) 0.027(3) Uiso d . 1
H H8B 0.4562(6) 1.100(2) 0.1792(11) 0.025(3) Uiso d . 1
H H8A 0.5085(6) 0.971(2) 0.1293(12) 0.026(3) Uiso d . 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 0.0226(4) 0.0197(4) 0.0195(4) -0.0036(3) 0.0063(3) -0.0004(3)
N1 0.0174(4) 0.0181(4) 0.0228(4) -0.0004(3) 0.0018(3) 0.0020(3)
C1 0.0170(4) 0.0178(4) 0.0144(4) 0.0026(3) 0.0015(3) -0.0002(3)
C2 0.0152(4) 0.0179(4) 0.0167(5) 0.0027(3) 0.0020(3) 0.0019(3)
C3 0.0190(5) 0.0191(5) 0.0196(5) 0.0007(4) 0.0006(4) -0.0027(4)
C4 0.0202(5) 0.0281(5) 0.0157(5) 0.0031(4) 0.0014(4) -0.0039(4)
C5 0.0177(5) 0.0271(5) 0.0161(5) 0.0012(4) 0.0031(4) 0.0016(4)
C6 0.0153(4) 0.0192(5) 0.0163(4) 0.0022(3) 0.0003(3) 0.0022(4)
C7 0.0164(4) 0.0197(5) 0.0189(5) 0.0008(4) 0.0026(4) 0.0056(4)
C8 0.0186(5) 0.0162(5) 0.0291(6) -0.0010(4) 0.0027(4) 0.0027(4)
C9 0.0226(5) 0.0189(5) 0.0255(5) -0.0033(4) 0.0025(4) 0.0019(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'
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'
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
C2 O1 C9 . . 117.53(8)
C7 N1 C8 . . 116.68(9)
C2 C1 C6 . . 120.12(9)
C2 C1 H1A . . 119.9
C6 C1 H1A . . 119.9
O1 C2 C1 . . 115.39(8)
O1 C2 C3 . . 124.31(9)
C1 C2 C3 . . 120.29(9)
C4 C3 C2 . . 119.28(9)
C4 C3 H3A . . 120.4
C2 C3 H3A . . 120.4
C5 C4 C3 . . 120.84(9)
C5 C4 H4A . . 119.6
C3 C4 H4A . . 119.6
C4 C5 C6 . . 120.01(9)
C4 C5 H5A . . 120.0
C6 C5 H5A . . 120.0
C1 C6 C5 . . 119.46(9)
C1 C6 C7 . . 121.54(9)
C5 C6 C7 . . 118.98(9)
N1 C7 C6 . . 123.50(9)
N1 C7 H7A . . 122.1(8)
C6 C7 H7A . . 114.4(8)
N1 C8 C8 . 2_655 111.10(7)
N1 C8 H8B . . 106.9(8)
C8 C8 H8B 2_655 . 108.8(8)
N1 C8 H8A . . 111.0(8)
C8 C8 H8A 2_655 . 110.5(7)
H8B C8 H8A . . 108.3(11)
O1 C9 H9A . . 109.5
O1 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
O1 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.3659(12)
O1 C9 . 1.4277(12)
N1 C7 . 1.2665(14)
N1 C8 . 1.4597(13)
C1 C2 . 1.3912(14)
C1 C6 . 1.3954(13)
C1 H1A . 0.9300
C2 C3 . 1.3958(14)
C3 C4 . 1.3899(14)
C3 H3A . 0.9300
C4 C5 . 1.3830(15)
C4 H4A . 0.9300
C5 C6 . 1.3993(14)
C5 H5A . 0.9300
C6 C7 . 1.4723(14)
C7 H7A . 0.999(13)
C8 C8 2_655 1.519(2)
C8 H8B . 0.984(13)
C8 H8A . 1.005(13)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
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
_geom_hbond_publ_flag
C9 H9A O1 4_545 0.9600 2.5000 3.3809(13) 153.00 y
C8 H8B Cg1 1_565 0.984(13) 2.822(13) 3.6221(12) 138.9(9) y
C9 H9C Cg1 7_555 0.9600 2.7500 3.5636(12) 143.00 y
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_4
_geom_torsion
C9 O1 C2 C1 . -179.56(8)
C9 O1 C2 C3 . -0.45(14)
C6 C1 C2 O1 . 177.98(8)
C6 C1 C2 C3 . -1.17(14)
O1 C2 C3 C4 . -178.19(9)
C1 C2 C3 C4 . 0.88(15)
C2 C3 C4 C5 . -0.27(15)
C3 C4 C5 C6 . -0.04(15)
C2 C1 C6 C5 . 0.84(14)
C2 C1 C6 C7 . -177.36(8)
C4 C5 C6 C1 . -0.24(15)
C4 C5 C6 C7 . 178.01(9)
C8 N1 C7 C6 . -179.92(9)
C1 C6 C7 N1 . 0.51(15)
C5 C6 C7 N1 . -177.70(10)
C7 N1 C8 C8 2_655 -136.92(11)
