#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227774
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jansrisewangwong, Patcharaporn'
'Chantrapromma, Suchada'
_publ_section_title
;
 (E,E)-1,2-Bis(2,4,6-trimethoxybenzylidene)hydrazine
;
_journal_coeditor_code           LH5117
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2401
_journal_page_last               o2402
_journal_paper_doi               10.1107/S1600536810033684
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H24 N2 O6'
_chemical_formula_moiety         'C20 H24 N2 O6'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41
_chemical_melting_point_gt       484
_chemical_melting_point_lt       486
_chemical_name_systematic
;
(E,E)-1,2-Bis(2,4,6-trimethoxybenzylidene)hydrazine
;
_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                71.4120(10)
_cell_angle_beta                 78.0950(10)
_cell_angle_gamma                79.4490(10)
_cell_formula_units_Z            1
_cell_length_a                   7.3851(2)
_cell_length_b                   7.4043(2)
_cell_length_c                   9.5440(2)
_cell_measurement_reflns_used    2791
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.28
_cell_volume                     480.13(2)
_computing_cell_refinement       'SAINT (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, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11100
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.1087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                2244
_reflns_number_total             2791
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5117.cif
_cod_data_source_block           I
_cod_database_code               2227774
_cod_database_fobs_code          2227774
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
O O1 0.20858(11) 0.87907(11) 0.08848(8) 0.01756(18) Uani d . 1 . .
O O2 0.82788(11) 0.57545(11) 0.12544(8) 0.01906(19) Uani d . 1 . .
O O3 0.44058(10) 0.78425(11) 0.53298(8) 0.01517(17) Uani d . 1 . .
N N1 0.09376(12) 0.95751(13) 0.49155(10) 0.0163(2) Uani d . 1 . .
C C1 0.35619(14) 0.81164(14) 0.16438(11) 0.0142(2) Uani d . 1 . .
C C2 0.52565(15) 0.72803(15) 0.10450(11) 0.0158(2) Uani d . 1 . .
H H2A 0.5443 0.7178 0.0078 0.019 Uiso calc R 1 . .
C C3 0.66759(14) 0.65957(15) 0.19168(11) 0.0148(2) Uani d . 1 . .
C C4 0.64415(14) 0.67699(14) 0.33540(11) 0.0143(2) Uani d . 1 . .
H H4A 0.7406 0.6318 0.3917 0.017 Uiso calc R 1 . .
C C5 0.47341(14) 0.76345(14) 0.39383(10) 0.0133(2) Uani d . 1 . .
C C6 0.32381(14) 0.83151(14) 0.31125(11) 0.0134(2) Uani d . 1 . .
C C7 0.14037(15) 0.91807(15) 0.36584(11) 0.0147(2) Uani d . 1 . .
C C8 0.22823(17) 0.85390(17) -0.05710(12) 0.0205(2) Uani d . 1 . .
H H8A 0.1127 0.9008 -0.0954 0.031 Uiso calc R 1 . .
H H8B 0.2601 0.7199 -0.0499 0.031 Uiso calc R 1 . .
H H8C 0.3251 0.9241 -0.1234 0.031 Uiso calc R 1 . .
C C9 0.96932(16) 0.47848(17) 0.21582(12) 0.0212(2) Uani d . 1 . .
H H9A 1.0697 0.4173 0.1585 0.032 Uiso calc R 1 . .
H H9B 0.9173 0.3834 0.3022 0.032 Uiso calc R 1 . .
H H9C 1.0157 0.5698 0.2473 0.032 Uiso calc R 1 . .
C C10 0.59168(15) 0.72427(16) 0.61730(11) 0.0167(2) Uani d . 1 . .
H H10A 0.5516 0.7495 0.7123 0.025 Uiso calc R 1 . .
H H10B 0.6945 0.7939 0.5631 0.025 Uiso calc R 1 . .
H H10C 0.6302 0.5892 0.6330 0.025 Uiso calc R 1 . .
H H7 0.0407(19) 0.9430(19) 0.3064(15) 0.022(3) Uiso d . 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
C1 O1 C8 . . 118.01(8) ?
C3 O2 C9 . . 117.79(8) ?
C5 O3 C10 . . 117.61(8) ?
C7 N1 N1 . 2_576 110.66(11) ?
O1 C1 C2 . . 122.94(9) ?
O1 C1 C6 . . 115.10(9) ?
C2 C1 C6 . . 121.95(9) ?
C1 C2 C3 . . 118.90(9) ?
C1 C2 H2A . . 120.5 ?
C3 C2 H2A . . 120.5 ?
O2 C3 C4 . . 123.44(9) ?
O2 C3 C2 . . 115.02(9) ?
C4 C3 C2 . . 121.55(9) ?
C3 C4 C5 . . 118.99(9) ?
C3 C4 H4A . . 120.5 ?
C5 C4 H4A . . 120.5 ?
O3 C5 C4 . . 122.15(9) ?
O3 C5 C6 . . 116.17(9) ?
C4 C5 C6 . . 121.67(9) ?
C5 C6 C1 . . 116.93(9) ?
C5 C6 C7 . . 124.92(9) ?
C1 C6 C7 . . 118.15(9) ?
N1 C7 C6 . . 125.41(9) ?
N1 C7 H7 . . 115.8(8) ?
C6 C7 H7 . . 118.7(8) ?
O1 C8 H8A . . 109.5 ?
O1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C9 H9A . . 109.5 ?
O2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O3 C10 H10A . . 109.5 ?
O3 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O3 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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
O1 C1 . 1.3632(12) ?
O1 C8 . 1.4347(12) ?
O2 C3 . 1.3642(12) ?
O2 C9 . 1.4328(13) ?
O3 C5 . 1.3528(11) ?
O3 C10 . 1.4322(12) ?
N1 C7 . 1.2882(13) ?
N1 N1 2_576 1.4117(18) ?
C1 C2 . 1.3866(14) ?
C1 C6 . 1.4226(13) ?
C2 C3 . 1.3944(15) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3909(13) ?
C4 C5 . 1.3974(14) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.4135(14) ?
C6 C7 . 1.4564(14) ?
C7 H7 . 0.976(14) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 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
C7 H7 O1 1_555 0.977(14) 2.332(14) 2.6886(12) 100.6(10) n
C10 H10B N1 2_676 0.96 2.49 3.3876(15) 155 y
C8 H8C Cg 2_675 0.97 2.79 3.6678(13) 152 y
C10 H10C Cg 2_666 0.97 2.63 3.4385(13) 142 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 O1 C1 C2 . . . . 2.86(15) ?
C8 O1 C1 C6 . . . . -176.61(9) ?
O1 C1 C2 C3 . . . . -178.70(9) ?
C6 C1 C2 C3 . . . . 0.74(16) ?
C9 O2 C3 C4 . . . . 8.39(15) ?
C9 O2 C3 C2 . . . . -171.46(9) ?
C1 C2 C3 O2 . . . . 178.49(9) ?
C1 C2 C3 C4 . . . . -1.37(16) ?
O2 C3 C4 C5 . . . . -179.18(9) ?
C2 C3 C4 C5 . . . . 0.67(16) ?
C10 O3 C5 C4 . . . . 3.58(14) ?
C10 O3 C5 C6 . . . . -177.40(8) ?
C3 C4 C5 O3 . . . . 179.66(9) ?
C3 C4 C5 C6 . . . . 0.69(15) ?
O3 C5 C6 C1 . . . . 179.70(8) ?
C4 C5 C6 C1 . . . . -1.27(15) ?
O3 C5 C6 C7 . . . . -0.86(15) ?
C4 C5 C6 C7 . . . . 178.16(9) ?
O1 C1 C6 C5 . . . . -179.97(8) ?
C2 C1 C6 C5 . . . . 0.55(15) ?
O1 C1 C6 C7 . . . . 0.55(14) ?
C2 C1 C6 C7 . . . . -178.93(9) ?
N1 N1 C7 C6 2_576 . . . 179.28(10) ?
C5 C6 C7 N1 . . . . 5.52(17) ?
C1 C6 C7 N1 . . . . -175.05(10) ?
