#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/54/2235411.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_2235411
loop_
_publ_author_name
'Zhang, Manman'
'Li, Li'
'Yuan, Fugen'
'Qian, Hui'
_publ_section_title
;
 4,4',6,6'-Tetra-tert-butyl-2,2'-[1,3-diazinane-1,3-diylbis(methylene)]diphenol
 0.25-hydrate
;
_journal_coeditor_code           FJ2558
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2123
_journal_paper_doi               10.1107/S1600536812026505
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C34 H54 N2 O2, 0.25H2 O'
_chemical_formula_moiety         'C34 H54 N2 O2, 0.25(H2 O)'
_chemical_formula_sum            'C136 H218 N8 O9'
_chemical_formula_weight         527.30
_chemical_name_systematic
;
4,4',6,6'-Tetra-tert-butyl-2,2'-[1,3-diazinane-1,3-
diylbis(methylene)]diphenol 0.25-hydrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7292(8)
_cell_length_b                   37.428(3)
_cell_length_c                   10.1806(9)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.58
_cell_volume                     3326.2(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'publCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29196
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1162
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.311
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0634P)²+1.2767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                3411
_reflns_number_total             3908
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2558.cif
_cod_data_source_block           I
_cod_original_cell_volume        3326.1(5)
_cod_database_code               2235411
_cod_database_fobs_code          2235411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
N N1 0.24037(12) 0.78185(2) 0.40084(10) 0.0226(2) Uani d . 1 1
O O1 0.50878(10) 0.81077(2) 0.47464(9) 0.0290(2) Uani d . 1 1
H H1 0.4572 0.7956 0.4369 0.044 Uiso calc R 1 1
O O2 0.7322(8) 0.7500 0.5233(7) 0.0500(15) Uiso d SPD 0.25 2
H H2 0.6880 0.7299 0.5133 0.075 Uiso d PRD 0.25 1
C C1 0.44073(13) 0.84373(3) 0.46035(11) 0.0218(2) Uani d . 1 1
C C2 0.30352(13) 0.84657(3) 0.38874(11) 0.0224(2) Uani d . 1 1
C C3 0.23273(13) 0.87966(3) 0.37546(12) 0.0228(2) Uani d . 1 1
H H3A 0.1408 0.8812 0.3297 0.027 Uiso calc R 1 1
C C4 0.29645(13) 0.91060(3) 0.42917(11) 0.0215(2) Uani d . 1 1
C C5 0.43413(13) 0.90681(3) 0.49783(11) 0.0220(2) Uani d . 1 1
H H5A 0.4783 0.9272 0.5335 0.026 Uiso calc R 1 1
C C6 0.50974(13) 0.87414(3) 0.51622(11) 0.0211(2) Uani d . 1 1
C C7 0.21487(13) 0.94668(3) 0.41266(12) 0.0248(3) Uani d . 1 1
C C8 0.05775(16) 0.94463(4) 0.47962(16) 0.0397(3) Uani d . 1 1
H H8A 0.0056 0.9671 0.4697 0.060 Uiso calc R 1 1
H H8B 0.0712 0.9395 0.5713 0.060 Uiso calc R 1 1
H H8C -0.0019 0.9260 0.4397 0.060 Uiso calc R 1 1
C C9 0.19124(19) 0.95464(4) 0.26617(16) 0.0429(4) Uani d . 1 1
H H9A 0.2890 0.9560 0.2232 0.064 Uiso calc R 1 1
H H9B 0.1386 0.9770 0.2565 0.064 Uiso calc R 1 1
H H9C 0.1314 0.9359 0.2272 0.064 Uiso calc R 1 1
C C10 0.30511(17) 0.97759(4) 0.4729(2) 0.0484(4) Uani d . 1 1
H H10A 0.4038 0.9792 0.4317 0.073 Uiso calc R 1 1
H H10B 0.3180 0.9735 0.5654 0.073 Uiso calc R 1 1
H H10C 0.2503 0.9995 0.4596 0.073 Uiso calc R 1 1
C C11 0.66220(13) 0.87198(3) 0.59218(11) 0.0240(3) Uani d . 1 1
C C12 0.71429(15) 0.90887(4) 0.64144(14) 0.0334(3) Uani d . 1 1
H H12A 0.6375 0.9187 0.6985 0.050 Uiso calc R 1 1
H H12B 0.7290 0.9245 0.5678 0.050 Uiso calc R 1 1
H H12C 0.8089 0.9065 0.6887 0.050 Uiso calc R 1 1
C C13 0.64494(16) 0.84776(4) 0.71373(13) 0.0365(3) Uani d . 1 1
H H13A 0.5661 0.8571 0.7698 0.055 Uiso calc R 1 1
H H13B 0.7401 0.8470 0.7609 0.055 Uiso calc R 1 1
H H13C 0.6178 0.8241 0.6862 0.055 Uiso calc R 1 1
C C14 0.78871(14) 0.85726(4) 0.50186(12) 0.0299(3) Uani d . 1 1
H H14A 0.7992 0.8725 0.4265 0.045 Uiso calc R 1 1
H H14B 0.7619 0.8336 0.4738 0.045 Uiso calc R 1 1
H H14C 0.8840 0.8565 0.5489 0.045 Uiso calc R 1 1
C C15 0.23842(15) 0.81429(3) 0.31813(12) 0.0261(3) Uani d . 1 1
H H15A 0.1338 0.8193 0.2919 0.031 Uiso calc R 1 1
H H15B 0.2976 0.8099 0.2391 0.031 Uiso calc R 1 1
C C16 0.2173(2) 0.7500 0.32086(16) 0.0228(3) Uani d S 1 2
H H16A 0.2891 0.7500 0.2481 0.027 Uiso calc SR 1 2
H H16B 0.1143 0.7500 0.2851 0.027 Uiso calc SR 1 2
C C17 0.12559(16) 0.78340(3) 0.50660(13) 0.0310(3) Uani d . 1 1
H H17A 0.0237 0.7850 0.4690 0.037 Uiso calc R 1 1
H H17B 0.1426 0.8045 0.5601 0.037 Uiso calc R 1 1
C C18 0.1380(3) 0.7500 0.59142(19) 0.0369(4) Uani d S 1 2
H H18A 0.2354 0.7500 0.6373 0.044 Uiso calc SR 1 2
H H18B 0.0569 0.7500 0.6565 0.044 Uiso calc SR 1 2
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
C16 N1 C17 . . 110.29(10)
C16 N1 C15 . . 110.62(9)
C17 N1 C15 . . 112.13(9)
C1 O1 H1 . . 109.5
O1 C1 C2 . . 119.33(10)
O1 C1 C6 . . 119.81(10)
C2 C1 C6 . . 120.85(10)
C3 C2 C1 . . 119.74(10)
C3 C2 C15 . . 119.80(10)
C1 C2 C15 . . 120.32(10)
C2 C3 C4 . . 121.57(10)
C2 C3 H3A . . 119.2
C4 C3 H3A . . 119.2
C3 C4 C5 . . 117.02(10)
C3 C4 C7 . . 120.11(10)
C5 C4 C7 . . 122.87(10)
C4 C5 C6 . . 124.06(10)
C4 C5 H5A . . 118.0
C6 C5 H5A . . 118.0
C5 C6 C1 . . 116.73(10)
C5 C6 C11 . . 121.28(10)
C1 C6 C11 . . 121.99(10)
C10 C7 C9 . . 108.21(12)
C10 C7 C8 . . 108.69(11)
C9 C7 C8 . . 108.76(11)
C10 C7 C4 . . 112.50(10)
C9 C7 C4 . . 109.83(10)
C8 C7 C4 . . 108.78(10)
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 . . 107.71(10)
C14 C11 C13 . . 109.83(10)
C12 C11 C13 . . 107.17(10)
C14 C11 C6 . . 109.79(9)
C12 C11 C6 . . 111.83(10)
C13 C11 C6 . . 110.44(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 C2 . . 112.34(9)
N1 C15 H15A . . 109.1
C2 C15 H15A . . 109.1
N1 C15 H15B . . 109.1
C2 C15 H15B . . 109.1
H15A C15 H15B . . 107.9
N1 C16 N1 . 7_575 109.75(13)
N1 C16 H16A . . 109.7
N1 C16 H16A 7_575 . 109.7
N1 C16 H16B . . 109.7
N1 C16 H16B 7_575 . 109.7
H16A C16 H16B . . 108.2
N1 C17 C18 . . 109.51(11)
N1 C17 H17A . . 109.8
C18 C17 H17A . . 109.8
N1 C17 H17B . . 109.8
C18 C17 H17B . . 109.8
H17A C17 H17B . . 108.2
C17 C18 C17 7_575 . 110.30(15)
C17 C18 H18A 7_575 . 109.6
C17 C18 H18A . . 109.6
C17 C18 H18B 7_575 . 109.6
C17 C18 H18B . . 109.6
H18A C18 H18B . . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C16 . 1.4575(13)
N1 C17 . 1.4719(16)
N1 C15 . 1.4777(14)
O1 C1 . 1.3770(13)
O1 H1 . 0.8200
O2 H2 . 0.8500
C1 C2 . 1.4062(16)
C1 C6 . 1.4078(15)
C2 C3 . 1.3909(15)
C2 C15 . 1.5162(15)
C3 C4 . 1.3962(15)
C3 H3A . 0.9300
C4 C5 . 1.3975(16)
C4 C7 . 1.5359(15)
C5 C6 . 1.4023(16)
C5 H5A . 0.9300
C6 C11 . 1.5414(15)
C7 C10 . 1.5283(17)
C7 C9 . 1.535(2)
C7 C8 . 1.5335(18)
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
C11 C14 . 1.5390(17)
C11 C12 . 1.5379(17)
C11 C13 . 1.5414(17)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 N1 7_575 1.4575(13)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C18 . 1.5231(16)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 C17 7_575 1.5231(16)
C18 H18A . 0.9700
C18 H18B . 0.9700
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
O1 H1 N1 . 0.82 2.00 2.6880(13) 142
O2 H2 O1 7_575 0.85 2.22 3.036(5) 161
