#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008308.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_2008308
loop_
_publ_author_name
'Laavanya. P'
'Panchanatheswaran. K'
'Murugadoss. R'
'Jeyaraman. R'
_publ_section_title
1,4-Diformyl-t-5-methyl-r-2,t-3-diphenylpiperazine-1,4-dicarbaldehyde
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              410
_journal_page_last               411
_journal_paper_doi               10.1107/S0108270198011779
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_chemical_name_systematic
;
  N₁,N₄-Diformyl-t-5-methyl-r-2,t-3-diphenylpiperazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.407(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.355(3)
_cell_length_b                   11.645(3)
_cell_length_c                   12.750(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.13
_cell_measurement_theta_min      4.12
_cell_volume                     1628.5(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Software Corporation,
(19XX)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics
;
ZORTEP (Zsolnai, 1997). Geometrical calculations: PARST (Nardelli, 1983)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3358
_diffrn_reflns_theta_max         70.13
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   '\y-scans (North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_description       cubic
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.266
_refine_ls_extinction_coef       0.0058(14)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1572P)²+0.2382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2266
_reflns_number_gt                2382
_reflns_number_total             3021
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vj1091.cif
_cod_data_source_block           lav
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1572P)^2^+0.2382P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.1572P)^2^+0.2382P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008308
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
N4 0.66874(15) 0.56348(15) 0.23883(14) 0.0474(5) Uani d . 1 . . N
C3 0.59273(17) 0.63564(17) 0.13723(17) 0.0440(5) Uani d . 1 . . C
H3 0.5389 0.5841 0.0738 0.071(2) Uiso calc R 1 . . H
C16 0.66733(18) 0.70274(17) 0.09047(17) 0.0450(5) Uani d . 1 . . C
O2 0.62820(16) 0.39832(14) 0.13242(15) 0.0649(5) Uani d . 1 . . O
N1 0.58374(16) 0.76717(15) 0.28458(16) 0.0490(5) Uani d . 1 . . N
C5 0.74201(19) 0.62279(19) 0.35071(19) 0.0534(6) Uani d . 1 . . C
H5A 0.8018 0.6711 0.3428 0.071(2) Uiso calc R 1 . . H
H5B 0.7855 0.5666 0.4120 0.071(2) Uiso calc R 1 . . H
C6 0.6628(2) 0.69610(19) 0.38653(19) 0.0544(6) Uani d . 1 . . C
H6 0.7173 0.7484 0.4486 0.071(2) Uiso calc R 1 . . H
C17 0.6104(2) 0.7823(2) 0.00014(19) 0.0524(5) Uani d . 1 . . C
H17 0.5273 0.7956 -0.0291 0.071(2) Uiso calc R 1 . . H
O1 0.51810(19) 0.94770(15) 0.2174(2) 0.0814(6) Uani d . 1 . . O
C2 0.51085(18) 0.71148(17) 0.16975(18) 0.0457(5) Uani d . 1 . . C
H2 0.4801 0.7730 0.1108 0.071(2) Uiso calc R 1 . . H
C8 0.6800(2) 0.45031(19) 0.2255(2) 0.0534(6) Uani d . 1 . . C
C10 0.39901(18) 0.65223(19) 0.16688(17) 0.0488(5) Uani d . 1 . . C
C7 0.5798(2) 0.8818(2) 0.2957(2) 0.0611(6) Uani d . 1 . . C
C18 0.6740(2) 0.8417(2) -0.0470(2) 0.0602(6) Uani d . 1 . . C
H18 0.6339 0.8949 -0.1070 0.071(2) Uiso calc R 1 . . H
C19 0.7972(2) 0.8225(2) -0.0054(2) 0.0619(6) Uani d . 1 . . C
H19 0.8408 0.8631 -0.0363 0.071(2) Uiso calc R 1 . . H
C20 0.8546(2) 0.7425(2) 0.0824(2) 0.0640(7) Uani d . 1 . . C
H20 0.9374 0.7286 0.1104 0.071(2) Uiso calc R 1 . . H
C11 0.3210(2) 0.7186(2) 0.1926(2) 0.0576(6) Uani d . 1 . . C
H11 0.3386 0.7958 0.2110 0.071(2) Uiso calc R 1 . . H
C21 0.79047(19) 0.68220(19) 0.1296(2) 0.0535(6) Uani d . 1 . . C
H21 0.8304 0.6276 0.1880 0.071(2) Uiso calc R 1 . . H
C9 0.5938(3) 0.6273(2) 0.4375(2) 0.0674(7) Uani d . 1 . . C
H9A 0.5389 0.6769 0.4501 0.095(6) Uiso calc R 1 . . H
H9B 0.6505 0.5938 0.5113 0.095(6) Uiso calc R 1 . . H
H9C 0.5482 0.5674 0.3833 0.095(6) Uiso calc R 1 . . H
C12 0.2186(2) 0.6723(3) 0.1915(2) 0.0714(8) Uani d . 1 . . C
H12 0.1672 0.7184 0.2085 0.071(2) Uiso calc R 1 . . H
C15 0.3705(2) 0.5376(2) 0.1393(2) 0.0617(6) Uani d . 1 . . C
H15 0.4210 0.4916 0.1209 0.071(2) Uiso calc R 1 . . H
C13 0.1911(3) 0.5581(3) 0.1654(3) 0.0821(9) Uani d . 1 . . C
H13 0.1220 0.5264 0.1656 0.071(2) Uiso calc R 1 . . H
C14 0.2673(3) 0.4911(3) 0.1390(3) 0.0792(8) Uani d . 1 . . C
H14 0.2491 0.4139 0.1208 0.071(2) Uiso calc R 1 . . H
H8 0.7350 0.4139 0.3095 0.061 Uiso d . 1 . . H
H7 0.6300 0.9079 0.3872 0.063 Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C8 N4 C5 122.2(2) yes
C8 N4 C3 120.8(2) yes
C5 N4 C3 116.6(2) yes
N4 C3 C16 112.53(15) ?
N4 C3 C2 108.95(16) ?
C16 C3 C2 113.75(17) ?
N4 C3 H3 107.1 ?
C16 C3 H3 107.1 ?
C2 C3 H3 107.1 ?
C21 C16 C17 117.8(2) ?
C21 C16 C3 122.14(18) ?
C17 C16 C3 119.94(17) ?
C7 N1 C6 120.5(2) yes
C7 N1 C2 120.5(2) yes
C6 N1 C2 119.0(2) yes
N4 C5 C6 111.30(17) ?
N4 C5 H5A 109.4 ?
C6 C5 H5A 109.4 ?
N4 C5 H5B 109.4 ?
C6 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
N1 C6 C9 113.61(19) ?
N1 C6 C5 107.98(17) ?
C9 C6 C5 113.5(2) ?
N1 C6 H6 107.1 ?
C9 C6 H6 107.1 ?
C5 C6 H6 107.1 ?
C18 C17 C16 121.6(2) ?
C18 C17 H17 119.2 ?
C16 C17 H17 119.2 ?
N1 C2 C10 110.81(17) ?
N1 C2 C3 110.17(15) ?
C10 C2 C3 115.72(17) ?
N1 C2 H2 106.5 ?
C10 C2 H2 106.5 ?
C3 C2 H2 106.5 ?
O2 C8 N4 124.9(2) ?
O2 C8 H8 126.3(2) ?
N4 C8 H8 108.70(19) ?
C15 C10 C11 118.3(2) ?
C15 C10 C2 124.2(2) ?
C11 C10 C2 117.5(2) ?
O1 C7 N1 125.5(2) ?
O1 C7 H7 122.7(2) ?
N1 C7 H7 111.2(2) ?
C17 C18 C19 120.1(2) ?
C17 C18 H18 120.0 ?
C19 C18 H18 120.0 ?
C20 C19 C18 119.1(2) ?
C20 C19 H19 120.4 ?
C18 C19 H19 120.4 ?
C19 C20 C21 120.9(2) ?
C19 C20 H20 119.6 ?
C21 C20 H20 119.6 ?
C12 C11 C10 121.2(3) ?
C12 C11 H11 119.4 ?
C10 C11 H11 119.4 ?
C16 C21 C20 120.5(2) ?
C16 C21 H21 119.7 ?
C20 C21 H21 119.7 ?
C6 C9 H9A 109.5 ?
C6 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C6 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C11 C12 C13 120.5(3) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C10 C15 C14 120.3(3) ?
C10 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C12 C13 C14 119.1(3) ?
C12 C13 H13 120.4 ?
C14 C13 H13 120.4 ?
C13 C14 C15 120.7(3) ?
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
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
N4 C8 . 1.344(3) yes
N4 C5 . 1.464(3) yes
N4 C3 . 1.465(2) yes
C3 C16 . 1.524(3) ?
C3 C2 . 1.537(3) ?
C3 H3 . 0.9800 ?
C16 C21 . 1.386(3) ?
C16 C17 . 1.390(3) ?
O2 C8 . 1.219(3) yes
N1 C7 . 1.345(3) yes
N1 C6 . 1.470(3) yes
N1 C2 . 1.470(3) yes
C5 C6 . 1.519(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C9 . 1.518(4) ?
C6 H6 . 0.9800 ?
C17 C18 . 1.376(3) ?
C17 H17 . 0.9300 ?
O1 C7 . 1.211(3) yes
C2 C10 . 1.530(3) yes
C2 H2 . 0.9800 ?
C8 H8 . 1.058(2) ?
C10 C15 . 1.384(3) ?
C10 C11 . 1.387(3) ?
C7 H7 . 1.082(3) ?
C18 C19 . 1.380(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.376(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.386(3) ?
C20 H20 . 0.9300 ?
C11 C12 . 1.370(3) ?
C11 H11 . 0.9300 ?
C21 H21 . 0.9300 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C12 C13 . 1.375(5) ?
C12 H12 . 0.9300 ?
C15 C14 . 1.384(3) ?
C15 H15 . 0.9300 ?
C13 C14 . 1.378(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
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
C8 N4 C3 C16 -100.2(2)
C5 N4 C3 C16 72.6(2)
C8 N4 C3 C2 132.7(2)
C5 N4 C3 C2 -54.5(2)
N4 C3 C16 C21 9.4(3)
C2 C3 C16 C21 133.9(2)
N4 C3 C16 C17 -174.93(18)
C2 C3 C16 C17 -50.4(2)
C8 N4 C5 C6 -130.7(2)
C3 N4 C5 C6 56.6(2)
C7 N1 C6 C9 106.3(2)
C2 N1 C6 C9 -74.9(2)
C7 N1 C6 C5 -126.9(2)
C2 N1 C6 C5 51.9(2)
N4 C5 C6 N1 -50.0(2)
N4 C5 C6 C9 76.9(2)
C21 C16 C17 C18 -1.9(3)
C3 C16 C17 C18 -177.82(19)
C7 N1 C2 C10 -103.9(2)
C6 N1 C2 C10 77.3(2)
C7 N1 C2 C3 126.7(2)
C6 N1 C2 C3 -52.1(2)
N4 C3 C2 N1 48.4(2)
C16 C3 C2 N1 -77.98(19)
N4 C3 C2 C10 -78.2(2)
C16 C3 C2 C10 155.37(16)
C5 N4 C8 O2 -174.2(2)
C3 N4 C8 O2 -1.8(4)
N1 C2 C10 C15 -125.3(2)
C3 C2 C10 C15 1.1(3)
N1 C2 C10 C11 55.4(2)
C3 C2 C10 C11 -178.32(17)
C6 N1 C7 O1 179.9(2)
C2 N1 C7 O1 1.1(4)
C16 C17 C18 C19 0.5(4)
C17 C18 C19 C20 0.8(4)
C18 C19 C20 C21 -0.5(4)
C15 C10 C11 C12 0.3(3)
C2 C10 C11 C12 179.7(2)
C17 C16 C21 C20 2.2(3)
C3 C16 C21 C20 178.0(2)
C19 C20 C21 C16 -1.0(4)
C10 C11 C12 C13 0.4(4)
C11 C10 C15 C14 -0.7(4)
C2 C10 C15 C14 179.9(2)
C11 C12 C13 C14 -0.8(4)
C12 C13 C14 C15 0.4(5)
C10 C15 C14 C13 0.4(4)
