#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/25/2232516.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_2232516
loop_
_publ_author_name
'Tee, Jia Ti'
'Abdullah, Norbani'
'Khaledi, Hamid'
_publ_section_title
;
 4,4',6,6'-Tetra-tert-butyl-2,2'-[butane-1,4-diylbis(nitrilomethanylylidene)]diphenol
;
_journal_coeditor_code           XU5350
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2954
_journal_paper_doi               10.1107/S1600536811041614
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C34 H52 N2 O2'
_chemical_formula_sum            'C34 H52 N2 O2'
_chemical_formula_weight         520.78
_chemical_name_systematic
;
4,4',6,6'-Tetra-tert-butyl-2,2'-[butane-1,4-
diylbis(nitrilomethanylylidene)]diphenol
;
_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'
_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                 90.3830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.1255(4)
_cell_length_b                   9.5702(2)
_cell_length_c                   8.63120(10)
_cell_measurement_reflns_used    4857
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      2.38
_cell_volume                     1579.78(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14602
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0428
_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)+(0.0533P)²+0.5079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                3039
_reflns_number_total             3631
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5350.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232516
_cod_database_fobs_code          2232516
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_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_symmetry_multiplicity
O O1 0.38365(4) 0.98230(9) 0.47339(10) 0.0267(2) Uani d . 1 1
H H1 0.4145(8) 0.9488(17) 0.3998(19) 0.040 Uiso d . 1 1
N N1 0.43079(5) 0.86964(11) 0.22286(12) 0.0276(2) Uani d . 1 1
C C1 0.31824(6) 0.96886(11) 0.41401(12) 0.0198(2) Uani d . 1 1
C C2 0.26044(6) 1.01998(11) 0.49629(12) 0.0193(2) Uani d . 1 1
C C3 0.19476(6) 1.00283(11) 0.42796(12) 0.0203(2) Uani d . 1 1
H H3 0.1553 1.0373 0.4824 0.024 Uiso calc R 1 1
C C4 0.18292(6) 0.93820(12) 0.28429(12) 0.0197(2) Uani d . 1 1
C C5 0.24129(6) 0.88907(11) 0.20702(12) 0.0196(2) Uani d . 1 1
H H5 0.2353 0.8443 0.1096 0.024 Uiso calc R 1 1
C C6 0.30834(6) 0.90361(11) 0.26843(12) 0.0194(2) Uani d . 1 1
C C7 0.26927(7) 1.09122(12) 0.65518(12) 0.0230(3) Uani d . 1 1
C C8 0.31935(8) 1.21639(13) 0.64423(15) 0.0348(3) Uani d . 1 1
H H8A 0.3004 1.2849 0.5707 0.052 Uiso calc R 1 1
H H8B 0.3651 1.1842 0.6085 0.052 Uiso calc R 1 1
H H8C 0.3244 1.2599 0.7465 0.052 Uiso calc R 1 1
C C9 0.29756(7) 0.98400(12) 0.77258(13) 0.0254(3) Uani d . 1 1
H H9A 0.3430 0.9492 0.7377 0.038 Uiso calc R 1 1
H H9B 0.2647 0.9058 0.7807 0.038 Uiso calc R 1 1
H H9C 0.3030 1.0286 0.8741 0.038 Uiso calc R 1 1
C C10 0.19963(7) 1.14567(14) 0.71697(14) 0.0323(3) Uani d . 1 1
H H10A 0.2074 1.1915 0.8172 0.049 Uiso calc R 1 1
H H10B 0.1672 1.0674 0.7300 0.049 Uiso calc R 1 1
H H10C 0.1797 1.2130 0.6434 0.049 Uiso calc R 1 1
C C11 0.10988(6) 0.92199(13) 0.21236(13) 0.0246(3) Uani d . 1 1
C C12 0.09358(7) 0.76642(15) 0.19055(17) 0.0357(3) Uani d . 1 1
H H12A 0.0932 0.7200 0.2918 0.053 Uiso calc R 1 1
H H12B 0.1294 0.7237 0.1252 0.053 Uiso calc R 1 1
H H12C 0.0477 0.7560 0.1407 0.053 Uiso calc R 1 1
C C13 0.10838(7) 0.99276(15) 0.05301(15) 0.0339(3) Uani d . 1 1
H H13A 0.0630 0.9757 0.0029 0.051 Uiso calc R 1 1
H H13B 0.1457 0.9542 -0.0114 0.051 Uiso calc R 1 1
H H13C 0.1154 1.0936 0.0656 0.051 Uiso calc R 1 1
C C14 0.05296(7) 0.9870(2) 0.31222(17) 0.0449(4) Uani d . 1 1
H H14A 0.0526 0.9413 0.4138 0.067 Uiso calc R 1 1
H H14B 0.0074 0.9745 0.2615 0.067 Uiso calc R 1 1
H H14C 0.0623 1.0870 0.3255 0.067 Uiso calc R 1 1
C C15 0.36766(6) 0.85464(12) 0.17746(13) 0.0225(2) Uani d . 1 1
H H15 0.3589 0.8100 0.0810 0.027 Uiso calc R 1 1
C C16 0.48707(6) 0.82786(14) 0.11850(16) 0.0312(3) Uani d . 1 1
H H16A 0.4676 0.7714 0.0324 0.037 Uiso calc R 1 1
H H16B 0.5214 0.7697 0.1755 0.037 Uiso calc R 1 1
C C17 0.52336(6) 0.95676(14) 0.05349(15) 0.0294(3) Uani d . 1 1
H H17A 0.5653 0.9268 -0.0045 0.035 Uiso calc R 1 1
H H17B 0.5393 1.0163 0.1407 0.035 Uiso calc R 1 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
C1 O1 H1 . . 107.4(10)
C15 N1 C16 . . 118.61(11)
O1 C1 C2 . . 120.20(10)
O1 C1 C6 . . 119.71(10)
C2 C1 C6 . . 120.09(10)
C3 C2 C1 . . 117.05(10)
C3 C2 C7 . . 121.48(10)
C1 C2 C7 . . 121.47(10)
C2 C3 C4 . . 124.44(10)
C2 C3 H3 . . 117.8
C4 C3 H3 . . 117.8
C5 C4 C3 . . 116.69(10)
C5 C4 C11 . . 120.36(10)
C3 C4 C11 . . 122.95(10)
C4 C5 C6 . . 121.73(10)
C4 C5 H5 . . 119.1
C6 C5 H5 . . 119.1
C5 C6 C1 . . 120.00(10)
C5 C6 C15 . . 118.70(10)
C1 C6 C15 . . 121.27(10)
C10 C7 C8 . . 107.48(10)
C10 C7 C9 . . 107.51(10)
C8 C7 C9 . . 110.11(10)
C10 C7 C2 . . 111.77(10)
C8 C7 C2 . . 110.79(9)
C9 C7 C2 . . 109.11(9)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C7 C9 H9A . . 109.5
C7 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C7 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C7 C10 H10A . . 109.5
C7 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C7 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C14 C11 C12 . . 108.67(12)
C14 C11 C4 . . 112.44(10)
C12 C11 C4 . . 109.40(10)
C14 C11 C13 . . 108.51(11)
C12 C11 C13 . . 108.45(10)
C4 C11 C13 . . 109.28(10)
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C11 C13 H13A . . 109.5
C11 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C11 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
C11 C14 H14A . . 109.5
C11 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C11 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N1 C15 C6 . . 122.40(10)
N1 C15 H15 . . 118.8
C6 C15 H15 . . 118.8
N1 C16 C17 . . 110.12(11)
N1 C16 H16A . . 109.6
C17 C16 H16A . . 109.6
N1 C16 H16B . . 109.6
C17 C16 H16B . . 109.6
H16A C16 H16B . . 108.1
C16 C17 C17 . 3_675 113.31(13)
C16 C17 H17A . . 108.9
C17 C17 H17A 3_675 . 108.9
C16 C17 H17B . . 108.9
C17 C17 H17B 3_675 . 108.9
H17A C17 H17B . . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.3549(14)
O1 H1 . 0.927(16)
N1 C15 . 1.2749(15)
N1 C16 . 1.4638(15)
C1 C2 . 1.4058(16)
C1 C6 . 1.4147(15)
C2 C3 . 1.3939(16)
C2 C7 . 1.5398(14)
C3 C4 . 1.4028(15)
C3 H3 . 0.9500
C4 C5 . 1.3863(15)
C4 C11 . 1.5328(16)
C5 C6 . 1.3914(16)
C5 H5 . 0.9500
C6 C15 . 1.4613(15)
C7 C10 . 1.5295(17)
C7 C8 . 1.5371(17)
C7 C9 . 1.5380(15)
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 C14 . 1.5257(18)
C11 C12 . 1.5325(18)
C11 C13 . 1.5332(16)
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
C13 H13A . 0.9800
C13 H13B . 0.9800
C13 H13C . 0.9800
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 H15 . 0.9500
C16 C17 . 1.5244(18)
C16 H16A . 0.9900
C16 H16B . 0.9900
C17 C17 3_675 1.525(3)
C17 H17A . 0.9900
C17 H17B . 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.927(16) 1.735(17) 2.5840(13) 150.8(14)
C8 H8B O1 0.98 2.29 2.9546(16) 124.6
C9 H9A O1 0.98 2.44 3.0720(15) 122.2
loop_
_iucr_refine_instructions_details
;
TITL 1 in P2(1)/c
CELL 0.71073  19.1255   9.5702   8.6312  90.000  90.383  90.000
ZERR    2.00   0.0004   0.0002   0.0001   0.000   0.001   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 68  104  4  4
OMIT 1 0 0
OMIT -2 55
L.S. 4
HTAB O1 H1
HTAB C8 O1
HTAB C9 O1
SIZE 0.26 0.15 0.06
ACTA
BOND $H
TEMP -173
WGHT    0.053300    0.507900
FVAR       0.18842
O1    4    0.383652    0.982303    0.473386    11.00000    0.02440    0.03115 =
         0.02458   -0.00317   -0.00296   -0.00357
H1    2    0.414519    0.948779    0.399847    11.00000   -1.50000
N1    3    0.430787    0.869637    0.222857    11.00000    0.02403    0.02888 =
         0.02994   -0.00027    0.00473   -0.00122
C1    1    0.318239    0.968864    0.414008    11.00000    0.02443    0.01521 =
         0.01959    0.00272   -0.00186   -0.00261
C2    1    0.260438    1.019982    0.496291    11.00000    0.02991    0.01260 =
         0.01552    0.00153   -0.00108    0.00091
C3    1    0.194756    1.002834    0.427956    11.00000    0.02726    0.01731 =
         0.01630    0.00101    0.00193    0.00514
AFIX  43
H3    2    0.155328    1.037261    0.482371    11.00000   -1.20000
AFIX   0
C4    1    0.182922    0.938195    0.284293    11.00000    0.02406    0.01834 =
         0.01666    0.00215   -0.00118    0.00111
C5    1    0.241287    0.889073    0.207020    11.00000    0.02715    0.01688 =
         0.01487   -0.00113    0.00047   -0.00142
AFIX  43
H5    2    0.235344    0.844309    0.109579    11.00000   -1.20000
AFIX   0
C6    1    0.308341    0.903613    0.268434    11.00000    0.02450    0.01504 =
         0.01881    0.00141    0.00235   -0.00133
C7    1    0.269265    1.091221    0.655175    11.00000    0.03648    0.01629 =
         0.01628   -0.00105   -0.00248    0.00068
C8    1    0.319350    1.216387    0.644230    11.00000    0.05967    0.02047 =
         0.02411   -0.00327   -0.00211   -0.00898
AFIX 137
H8A   2    0.300427    1.284861    0.570676    11.00000   -1.50000
H8B   2    0.365149    1.184236    0.608544    11.00000   -1.50000
H8C   2    0.324408    1.259865    0.746491    11.00000   -1.50000
AFIX   0
C9    1    0.297557    0.984002    0.772584    11.00000    0.03792    0.02036 =
         0.01783   -0.00040   -0.00585    0.00023
AFIX 137
H9A   2    0.343008    0.949217    0.737741    11.00000   -1.50000
H9B   2    0.264686    0.905829    0.780688    11.00000   -1.50000
H9C   2    0.303004    1.028639    0.874136    11.00000   -1.50000
AFIX   0
C10   1    0.199630    1.145674    0.716971    11.00000    0.04741    0.03013 =
         0.01948   -0.00638   -0.00108    0.01176
AFIX 137
H10A  2    0.207378    1.191507    0.817157    11.00000   -1.50000
H10B  2    0.167163    1.067390    0.729970    11.00000   -1.50000
H10C  2    0.179731    1.213016    0.643380    11.00000   -1.50000
AFIX   0
C11   1    0.109879    0.921986    0.212356    11.00000    0.02422    0.03009 =
         0.01941   -0.00045   -0.00210    0.00251
C12   1    0.093579    0.766417    0.190550    11.00000    0.02888    0.03463 =
         0.04338    0.00438   -0.00530   -0.00810
AFIX 137
H12A  2    0.093202    0.720028    0.291765    11.00000   -1.50000
H12B  2    0.129432    0.723707    0.125219    11.00000   -1.50000
H12C  2    0.047680    0.756029    0.140724    11.00000   -1.50000
AFIX   0
C13   1    0.108384    0.992762    0.053010    11.00000    0.03779    0.03741 =
         0.02633    0.00572   -0.01183   -0.00421
AFIX 137
H13A  2    0.063041    0.975739    0.002934    11.00000   -1.50000
H13B  2    0.145725    0.954229   -0.011399    11.00000   -1.50000
H13C  2    0.115430    1.093560    0.065643    11.00000   -1.50000
AFIX   0
C14   1    0.052957    0.986990    0.312217    11.00000    0.02716    0.07462 =
         0.03269   -0.01158   -0.00633    0.01713
AFIX 137
H14A  2    0.052561    0.941285    0.413812    11.00000   -1.50000
H14B  2    0.007398    0.974486    0.261458    11.00000   -1.50000
H14C  2    0.062350    1.086953    0.325525    11.00000   -1.50000
AFIX   0
C15   1    0.367664    0.854642    0.177458    11.00000    0.02757    0.01839 =
         0.02149   -0.00008    0.00348   -0.00200
AFIX  43
H15   2    0.358872    0.810005    0.080967    11.00000   -1.20000
AFIX   0
C16   1    0.487065    0.827861    0.118500    11.00000    0.02452    0.03142 =
         0.03770   -0.00091    0.00753    0.00214
AFIX  23
H16A  2    0.467554    0.771359    0.032408    11.00000   -1.20000
H16B  2    0.521421    0.769653    0.175539    11.00000   -1.20000
AFIX   0
C17   1    0.523364    0.956760    0.053489    11.00000    0.01925    0.03551 =
         0.03338   -0.00317    0.00373   -0.00144
AFIX  23
H17A  2    0.565269    0.926832   -0.004482    11.00000   -1.20000
H17B  2    0.539284    1.016255    0.140674    11.00000   -1.20000
HKLF 4
REM  1 in P2(1)/c
REM R1 =  0.0428 for   3039 Fo > 4sig(Fo)  and  0.0526 for all   3631 data
REM    181 parameters refined using      0 restraints
END
WGHT      0.0527      0.5132
REM Highest difference peak  0.301,  deepest hole -0.158,  1-sigma level  0.037
Q1    1   0.3367  0.8735  0.2328  11.00000  0.05    0.30
Q2    1   0.3133  0.9348  0.3365  11.00000  0.05    0.29
Q3    1   0.2896  1.0151  0.4493  11.00000  0.05    0.29
Q4    1   0.2651  1.0493  0.5751  11.00000  0.05    0.28
;
