#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220615.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_2220615
loop_
_publ_author_name
'Bortoluzzi, Adailton J.'
'Bisol, Tula B.'
'Sá, Marcus M.'
_publ_section_title
;
 (E,E)-Methyl
 2-[(3-nitrobenzylidene)aminomethyl]-3-phenylpropenoate
;
_journal_coeditor_code           RZ2278
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o198
_journal_page_last               o199
_journal_paper_doi               10.1107/S1600536808043262
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C18 H16 N2 O4'
_chemical_formula_sum            'C18 H16 N2 O4'
_chemical_formula_weight         324.33
_chemical_name_systematic
;
(E,E)-Methyl
2-[(3-nitrobenzylidene)aminomethyl]-3-phenylpropenoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.275(18)
_cell_angle_beta                 76.526(13)
_cell_angle_gamma                63.158(14)
_cell_formula_units_Z            2
_cell_length_a                   8.6035(12)
_cell_length_b                   8.7829(14)
_cell_length_c                   12.4680(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.70
_cell_measurement_theta_min      5.33
_cell_volume                     813.9(2)
_computing_cell_refinement
;
SET4 in CAD-4 Software (Enraf--Nonius, 1989)
;
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics
;
PLATON (Spek, 2003); Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3026
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0432
_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)+(0.0588P)²+0.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2165
_reflns_number_total             2883
_reflns_threshold_expression     '> 2σ (I)'
_cod_data_source_file            rz2278.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2220615
_cod_database_fobs_code          2220615
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.1755(2) 0.5606(2) 0.77725(14) 0.0470(4) Uani d . 1 . .
H H1 0.1648 0.6615 0.7983 0.056 Uiso calc R 1 . .
N N2 0.1722(2) 0.55429(18) 0.67793(12) 0.0492(4) Uani d . 1 . .
C C3 0.1642(3) 0.7065(2) 0.60179(15) 0.0514(5) Uani d . 1 . .
H H3A 0.2700 0.6741 0.5459 0.062 Uiso calc R 1 . .
H H3B 0.1627 0.7908 0.6430 0.062 Uiso calc R 1 . .
C C4 0.0043(2) 0.7874(2) 0.54518(14) 0.0465(4) Uani d . 1 . .
C C5 0.0074(2) 0.7661(2) 0.44100(14) 0.0488(4) Uani d . 1 . .
H H5 -0.0960 0.8330 0.4121 0.059 Uiso calc R 1 . .
C C6 -0.1594(3) 0.9030(2) 0.61246(15) 0.0515(5) Uani d . 1 . .
O O7 -0.1704(2) 0.91839(19) 0.70815(11) 0.0734(4) Uani d . 1 . .
O O8 -0.29582(18) 0.98968(18) 0.55747(11) 0.0639(4) Uani d . 1 . .
C C9 -0.4579(3) 1.1040(3) 0.6204(2) 0.0796(7) Uani d . 1 . .
H H9A -0.4923 1.0411 0.6855 0.119 Uiso calc R 1 . .
H H9B -0.5493 1.1532 0.5758 0.119 Uiso calc R 1 . .
H H9C -0.4398 1.1936 0.6416 0.119 Uiso calc R 1 . .
C C11 0.1958(2) 0.4135(2) 0.86183(14) 0.0446(4) Uani d . 1 . .
C C12 0.1900(2) 0.2681(2) 0.83818(13) 0.0434(4) Uani d . 1 . .
H H12 0.1726 0.2610 0.7687 0.052 Uiso calc R 1 . .
C C13 0.2104(2) 0.1340(2) 0.91989(14) 0.0471(4) Uani d . 1 . .
N N13 0.2048(2) -0.01950(19) 0.89347(14) 0.0573(4) Uani d . 1 . .
O O14 0.2052(2) -0.03191(17) 0.79774(13) 0.0745(5) Uani d . 1 . .
O O15 0.2022(3) -0.13071(19) 0.96882(14) 0.0879(5) Uani d . 1 . .
C C14 0.2357(3) 0.1386(3) 1.02445(15) 0.0579(5) Uani d . 1 . .
H H14 0.2487 0.0465 1.0780 0.069 Uiso calc R 1 . .
C C15 0.2412(3) 0.2832(3) 1.04694(16) 0.0625(5) Uani d . 1 . .
H H15 0.2582 0.2896 1.1166 0.075 Uiso calc R 1 . .
C C16 0.2215(3) 0.4193(3) 0.96652(15) 0.0555(5) Uani d . 1 . .
H H16 0.2255 0.5163 0.9829 0.067 Uiso calc R 1 . .
C C21 0.1565(2) 0.6482(2) 0.36716(14) 0.0465(4) Uani d . 1 . .
C C22 0.1946(3) 0.7024(2) 0.25635(15) 0.0546(5) Uani d . 1 . .
H H22 0.1252 0.8133 0.2294 0.066 Uiso calc R 1 . .
C C23 0.3330(3) 0.5951(3) 0.18584(17) 0.0615(5) Uani d . 1 . .
H H23 0.3578 0.6345 0.1122 0.074 Uiso calc R 1 . .
C C24 0.4353(3) 0.4296(3) 0.22366(18) 0.0631(5) Uani d . 1 . .
H H24 0.5284 0.3567 0.1758 0.076 Uiso calc R 1 . .
C C25 0.3986(3) 0.3727(3) 0.33283(19) 0.0660(6) Uani d . 1 . .
H H25 0.4671 0.2607 0.3585 0.079 Uiso calc R 1 . .
C C26 0.2610(3) 0.4802(2) 0.40479(17) 0.0575(5) Uani d . 1 . .
H H26 0.2379 0.4405 0.4785 0.069 Uiso calc R 1 . .
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
_geom_angle_publ_flag
N2 C1 C11 . . 122.48(16) ?
N2 C1 H1 . . 118.8 ?
C11 C1 H1 . . 118.8 ?
C1 N2 C3 . . 116.16(15) ?
N2 C3 C4 . . 113.24(14) ?
N2 C3 H3A . . 108.9 ?
C4 C3 H3A . . 108.9 ?
N2 C3 H3B . . 108.9 ?
C4 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
C5 C4 C6 . . 121.26(17) ?
C5 C4 C3 . . 124.23(17) ?
C6 C4 C3 . . 114.43(16) ?
C4 C5 C21 . . 127.15(17) ?
C4 C5 H5 . . 116.4 ?
C21 C5 H5 . . 116.4 ?
O7 C6 O8 . . 122.52(18) ?
O7 C6 C4 . . 123.31(18) ?
O8 C6 C4 . . 114.17(16) ?
C6 O8 C9 . . 115.78(16) ?
O8 C9 H9A . . 109.5 ?
O8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C16 C11 C12 . . 118.96(16) ?
C16 C11 C1 . . 120.11(16) ?
C12 C11 C1 . . 120.93(15) ?
C13 C12 C11 . . 118.65(16) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 122.84(17) ?
C12 C13 N13 . . 118.04(16) ?
C14 C13 N13 . . 119.12(16) ?
O14 N13 O15 . . 122.86(17) ?
O14 N13 C13 . . 118.70(15) ?
O15 N13 C13 . . 118.44(17) ?
C15 C14 C13 . . 118.01(17) ?
C15 C14 H14 . . 121.0 ?
C13 C14 H14 . . 121.0 ?
C14 C15 C16 . . 120.37(18) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C11 . . 121.17(18) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
C22 C21 C26 . . 118.14(17) ?
C22 C21 C5 . . 120.03(16) ?
C26 C21 C5 . . 121.82(16) ?
C23 C22 C21 . . 121.17(18) ?
C23 C22 H22 . . 119.4 ?
C21 C22 H22 . . 119.4 ?
C22 C23 C24 . . 120.28(19) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C25 C24 C23 . . 119.5(2) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C24 C25 C26 . . 120.70(19) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C21 . . 120.21(19) ?
C25 C26 H26 . . 119.9 ?
C21 C26 H26 . . 119.9 ?
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
C1 N2 . 1.257(2) ?
C1 C11 . 1.478(2) ?
C1 H1 . 0.9300 ?
N2 C3 . 1.473(2) ?
C3 C4 . 1.509(2) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.339(2) ?
C4 C6 . 1.481(3) ?
C5 C21 . 1.473(2) ?
C5 H5 . 0.9300 ?
C6 O7 . 1.203(2) ?
C6 O8 . 1.342(2) ?
O8 C9 . 1.445(2) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C11 C16 . 1.387(2) ?
C11 C12 . 1.388(2) ?
C12 C13 . 1.380(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.381(3) ?
C13 N13 . 1.470(2) ?
N13 O14 . 1.218(2) ?
N13 O15 . 1.227(2) ?
C14 C15 . 1.373(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.383(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C21 C22 . 1.389(3) ?
C21 C26 . 1.395(3) ?
C22 C23 . 1.373(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.376(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.375(3) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.382(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
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
C23 H23 O15 1_564 0.93 2.55 3.307(3) 139.0
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C1 N2 C3 . . . . -175.74(16) ?
C1 N2 C3 C4 . . . . -121.34(18) ?
N2 C3 C4 C5 . . . . -101.1(2) ?
N2 C3 C4 C6 . . . . 82.07(19) ?
C6 C4 C5 C21 . . . . -175.96(15) ?
C3 C4 C5 C21 . . . . 7.5(3) ?
C5 C4 C6 O7 . . . . 175.67(18) ?
C3 C4 C6 O7 . . . . -7.4(2) ?
C5 C4 C6 O8 . . . . -4.2(2) ?
C3 C4 C6 O8 . . . . 172.71(14) ?
O7 C6 O8 C9 . . . . 0.2(3) ?
C4 C6 O8 C9 . . . . -179.94(16) ?
N2 C1 C11 C16 . . . . 171.68(18) ?
N2 C1 C11 C12 . . . . -8.2(3) ?
C16 C11 C12 C13 . . . . -0.1(3) ?
C1 C11 C12 C13 . . . . 179.71(16) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
C11 C12 C13 N13 . . . . -179.70(15) ?
C12 C13 N13 O14 . . . . 9.2(3) ?
C14 C13 N13 O14 . . . . -170.73(18) ?
C12 C13 N13 O15 . . . . -171.67(17) ?
C14 C13 N13 O15 . . . . 8.4(3) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
N13 C13 C14 C15 . . . . 179.74(18) ?
C13 C14 C15 C16 . . . . 0.1(3) ?
C14 C15 C16 C11 . . . . 0.0(3) ?
C12 C11 C16 C15 . . . . 0.0(3) ?
C1 C11 C16 C15 . . . . -179.85(18) ?
C4 C5 C21 C22 . . . . -138.14(19) ?
C4 C5 C21 C26 . . . . 42.9(3) ?
C26 C21 C22 C23 . . . . -1.1(3) ?
C5 C21 C22 C23 . . . . 179.90(17) ?
C21 C22 C23 C24 . . . . 1.2(3) ?
C22 C23 C24 C25 . . . . -0.5(3) ?
C23 C24 C25 C26 . . . . -0.3(3) ?
C24 C25 C26 C21 . . . . 0.4(3) ?
C22 C21 C26 C25 . . . . 0.3(3) ?
C5 C21 C26 C25 . . . . 179.29(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741464
