#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/70/2007067.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_2007067
loop_
_publ_author_name
'Thirumurugan, R.'
'Shanmuga Sundara Raj, S.'
'Shanmugam, G.'
'Chinnakali, Kandasamy'
'Razak, Ibrahim Abdul'
'Fun, Hoong-Kun'
'Marappan, M.'
'Kandaswamy, M.'
_publ_section_title
1,4-Bis[3-(N-cyclohexyliminomethyl)-2-hydroxy-5-methylbenzyl]piperazine
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              365
_journal_page_last               367
_journal_paper_doi               10.1107/S0108270197016934
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C34 H48 N4 O2'
_chemical_formula_sum            'C34 H48 N4 O2'
_chemical_formula_weight         544.76
_chemical_melting_point          481.15
_chemical_name_systematic
;
2,2'-piperazin-1,4-diyldimethylene-bis[6-(cyclohexyliminimethyl)
-4-methylphenol]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.996(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4598(10)
_cell_length_b                   12.5892(11)
_cell_length_c                   11.1347(12)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.48
_cell_measurement_theta_min      5.42
_cell_volume                     1590.8(3)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/2θ
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            4545
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.0147(18)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   0.866
_refine_ls_goodness_of_fit_obs   1.085
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.866
_refine_ls_restrained_S_obs      1.085
_refine_ls_R_factor_all          0.096
_refine_ls_R_factor_obs          .043
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0624P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.124
_refine_ls_wR_factor_obs         .105
_reflns_number_observed          1787
_reflns_number_total             3635
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            bm1205.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '208\%C' was changed to '481.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '208\%C' was changed to '481.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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^)+(0.0624P)^2^] 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^)+(0.0624P)^2^]
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/c'
_cod_database_code               2007067
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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .27216(10) -.08552(11) -.36285(11) .0733(4) Uani d . 1 . O
N1 .29332(12) -.13104(12) -.58943(12) .0661(4) Uani d . 1 . N
N2 .05156(11) -.05390(10) -.09307(11) .0574(4) Uani d . 1 . N
C1 .15628(13) -.11031(12) -.39180(14) .0542(4) Uani d . 1 . C
C2 .10999(13) -.14335(12) -.50877(14) .0546(4) Uani d . 1 . C
C3 -.00925(15) -.16799(14) -.5333(2) .0599(4) Uani d . 1 . C
C4 -.08319(14) -.16207(13) -.4462(2) .0605(4) Uani d . 1 . C
C5 -.03322(14) -.13063(13) -.3298(2) .0586(4) Uani d . 1 . C
C6 .08454(13) -.10343(12) -.30081(14) .0552(4) Uani d . 1 . C
C7 -.2124(2) -.1869(3) -.4743(3) .0886(7) Uani d . 1 . C
C8 .1848(2) -.15384(14) -.6038(2) .0591(4) Uani d . 1 . C
C9 .3580(2) -.1443(2) -.6932(2) .0665(5) Uani d . 1 . C
C10 .3971(3) -.0376(2) -.7335(2) .0891(7) Uani d . 1 . C
C11 .4650(3) -.0487(2) -.8413(3) .1028(8) Uani d . 1 . C
C12 .5680(2) -.1246(2) -.8126(3) .0955(8) Uani d . 1 . C
C13 .5304(2) -.2301(2) -.7684(2) .0912(7) Uani d . 1 . C
C14 .4610(2) -.2184(2) -.6619(2) .0800(6) Uani d . 1 . C
C15 .1380(2) -.0684(2) -.1757(2) .0668(5) Uani d . 1 . C
C16 -.0110(2) .0463(2) -.1146(2) .0657(5) Uani d . 1 . C
C17 .1048(2) -.0574(2) .03336(15) .0652(5) Uani d . 1 . C
H1O1 .3023(17) -.0942(16) -.4292(19) .092(7) Uiso d . 1 . H
H3 -.0388(13) -.1900(12) -.6112(15) .057(4) Uiso d . 1 . H
H5 -.0832(13) -.1302(12) -.2680(14) .058(4) Uiso d . 1 . H
H7A -.226(2) -.249(2) -.527(2) .137(10) Uiso d . 1 . H
H7B -.240(2) -.224(3) -.413(3) .156(12) Uiso d . 1 . H
H7C -.260(3) -.126(3) -.491(3) .190(15) Uiso d . 1 . H
H8 .1437(13) -.1821(13) -.6798(16) .067(5) Uiso d . 1 . H
H9 .3005(14) -.1753(14) -.7610(16) .078(5) Uiso d . 1 . H
H10A .4507(19) -.0117(18) -.664(2) .103(8) Uiso d . 1 . H
H10B .324(2) .0101(19) -.753(2) .119(8) Uiso d . 1 . H
H11A .495(2) .023(2) -.859(3) .153(11) Uiso d . 1 . H
H11B .415(2) -.082(2) -.913(2) .122(9) Uiso d . 1 . H
H12A .6081(18) -.1338(16) -.882(2) .099(6) Uiso d . 1 . H
H12B .6268(19) -.1006(18) -.746(2) .108(8) Uiso d . 1 . H
H13A .4747(18) -.2625(18) -.8380(19) .103(7) Uiso d . 1 . H
H13B .605(2) -.280(2) -.743(2) .136(9) Uiso d . 1 . H
H14A .428(2) -.291(2) -.636(2) .125(8) Uiso d . 1 . H
H14B .5098(18) -.1885(17) -.595(2) .100(7) Uiso d . 1 . H
H15A .1848(16) -.0028(15) -.1837(17) .084(6) Uiso d . 1 . H
H15B .1985(18) -.1257(17) -.1404(19) .107(7) Uiso d . 1 . H
H16A -.0481(14) .0465(13) -.1997(16) .074(5) Uiso d . 1 . H
H16B .0462(15) .1061(15) -.0976(17) .081(6) Uiso d . 1 . H
H17A .1680(15) .0010(15) .0487(16) .080(6) Uiso d . 1 . H
H17B .1472(15) -.1286(15) .0467(16) .084(6) 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 0.0033 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_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C9 . 118.1(2) ?
C16 N2 C17 . 108.45(13) yes
C16 N2 C15 . 111.61(14) yes
C17 N2 C15 . 112.19(13) yes
O1 C1 C6 . 117.99(15) ?
O1 C1 C2 . 121.37(14) ?
C6 C1 C2 . 120.63(14) ?
C3 C2 C1 . 118.93(15) ?
C3 C2 C8 . 119.9(2) ?
C1 C2 C8 . 121.15(15) ?
C4 C3 C2 . 122.3(2) ?
C3 C4 C5 . 117.07(15) ?
C3 C4 C7 . 121.8(2) ?
C5 C4 C7 . 121.1(2) ?
C6 C5 C4 . 123.1(2) ?
C5 C6 C1 . 117.96(15) ?
C5 C6 C15 . 123.05(14) ?
C1 C6 C15 . 118.99(14) ?
N1 C8 C2 . 123.7(2) ?
N1 C9 C10 . 109.7(2) ?
N1 C9 C14 . 110.7(2) ?
C10 C9 C14 . 111.5(2) ?
C9 C10 C11 . 111.0(2) ?
C12 C11 C10 . 111.0(2) ?
C13 C12 C11 . 112.1(2) ?
C12 C13 C14 . 112.0(2) ?
C9 C14 C13 . 110.9(2) ?
N2 C15 C6 . 113.33(14) ?
N2 C16 C17 3 110.98(15) ?
N2 C17 C16 3 109.92(14) ?
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 . 1.358(2) yes
N1 C8 . 1.265(2) yes
N1 C9 . 1.467(2) yes
N2 C16 . 1.454(2) yes
N2 C17 . 1.455(2) yes
N2 C15 . 1.455(2) yes
C1 C6 . 1.393(2) ?
C1 C2 . 1.399(2) ?
C2 C3 . 1.391(2) ?
C2 C8 . 1.457(2) yes
C3 C4 . 1.375(2) ?
C4 C5 . 1.399(2) ?
C4 C7 . 1.503(3) ?
C5 C6 . 1.386(2) ?
C6 C15 . 1.507(2) yes
C9 C10 . 1.503(3) ?
C9 C14 . 1.506(3) ?
C10 C11 . 1.526(3) ?
C11 C12 . 1.518(4) ?
C12 C13 . 1.500(3) ?
C13 C14 . 1.524(3) ?
C16 C17 3 1.505(2) ?
C17 C16 3 1.505(2) ?
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
O1 C1 C2 C3 . 179.84(15)
C6 C1 C2 C3 . 0.8(2)
O1 C1 C2 C8 . 0.8(2)
C6 C1 C2 C8 . -178.19(15)
C1 C2 C3 C4 . -0.7(2)
C8 C2 C3 C4 . 178.3(2)
C2 C3 C4 C5 . -0.5(2)
C2 C3 C4 C7 . 178.8(2)
C3 C4 C5 C6 . 1.6(2)
C7 C4 C5 C6 . -177.7(2)
C4 C5 C6 C1 . -1.5(2)
C4 C5 C6 C15 . 179.3(2)
O1 C1 C6 C5 . -178.83(14)
C2 C1 C6 C5 . 0.2(2)
O1 C1 C6 C15 . 0.4(2)
C2 C1 C6 C15 . 179.5(2)
C9 N1 C8 C2 . -179.37(15)
C3 C2 C8 N1 . 178.5(2)
C1 C2 C8 N1 . -2.5(3)
C8 N1 C9 C10 . 113.8(2)
C8 N1 C9 C14 . -122.8(2)
N1 C9 C10 C11 . 179.9(2)
C14 C9 C10 C11 . 56.9(3)
C9 C10 C11 C12 . -55.0(3)
C10 C11 C12 C13 . 53.6(3)
C11 C12 C13 C14 . -53.3(3)
N1 C9 C14 C13 . -178.5(2)
C10 C9 C14 C13 . -56.1(3)
C12 C13 C14 C9 . 54.2(3)
C16 N2 C15 C6 . -78.3(2)
C17 N2 C15 C6 . 159.7(2)
C5 C6 C15 N2 . -6.9(3)
C1 C6 C15 N2 . 173.88(15)
C17 N2 C16 C17 3 -59.2(2)
C15 N2 C16 C17 3 176.76(15)
C16 N2 C17 C16 3 58.5(2)
C15 N2 C17 C16 3 -177.8(2)
