#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/22/2212204.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_2212204
loop_
_publ_author_name
'Xing, Zhi-Tao'
'Ding, Wei-Lin'
'Wang, Hai-Bo'
'Wu, Wen-Yuan'
'Yin, Jun'
_publ_section_title
6,6'-Bis(2H-1,2,3-benzotriazol-2-yl)-4,4'-bis(2,4,4-trimethylpentan-2-yl)-2,2'-methylenebiphenol
_journal_coeditor_code           HB2269
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o819
_journal_page_last               o820
_journal_paper_doi               10.1107/S1600536807002474
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C41 H50 N6 O2'
_chemical_formula_moiety         'C41 H50 N6 O2'
_chemical_formula_sum            'C41 H50 N6 O2'
_chemical_formula_weight         658.87
_chemical_name_systematic
;
6,6'-Bis(2H-1,2,3-benzotriazol-2-yl)-4,4'-bis(2,4,4-trimethylpentan-2-yl)-
2,2'-methylenebiphenol
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.302(4)
_cell_length_b                   8.0960(16)
_cell_length_c                   24.553(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     3638.1(13)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD4'
_diffrn_measurement_method       ω/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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3587
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1919
_refine_ls_R_factor_gt           0.0896
_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)+(0.0503P)²+1.8628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                1789
_reflns_number_total             3545
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2269.cif
_cod_data_source_block           I
_cod_database_code               2212204
_cod_database_fobs_code          2212204
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
O O1 0.14203(15) 0.7076(4) 0.21973(11) 0.0718(9) Uani d . 1
H H1 0.1820 0.7381 0.2084 0.108 Uiso calc R 1
N N1 0.17421(18) 0.9035(5) 0.12466(15) 0.0580(10) Uani d . 1
N N2 0.18825(19) 0.9850(5) 0.07846(15) 0.0668(11) Uani d . 1
N N3 0.23242(19) 0.8502(5) 0.15319(14) 0.0681(12) Uani d . 1
C C1 -0.1437(3) 1.3550(6) 0.1379(2) 0.0943(18) Uani d . 1
H H1A -0.1469 1.4451 0.1632 0.141 Uiso calc R 1
H H1B -0.1855 1.3564 0.1142 0.141 Uiso calc R 1
H H1C -0.1000 1.3661 0.1165 0.141 Uiso calc R 1
C C2 -0.2059(3) 1.1957(7) 0.2090(2) 0.0912(18) Uani d . 1
H H2A -0.2044 1.0999 0.2320 0.137 Uiso calc R 1
H H2B -0.2509 1.1966 0.1889 0.137 Uiso calc R 1
H H2C -0.2027 1.2934 0.2310 0.137 Uiso calc R 1
C C3 -0.0710(2) 1.1852(6) 0.2017(2) 0.0895(18) Uani d . 1
H H3A -0.0691 1.2777 0.2261 0.134 Uiso calc R 1
H H3B -0.0301 1.1897 0.1773 0.134 Uiso calc R 1
H H3C -0.0691 1.0844 0.2223 0.134 Uiso calc R 1
C C4 -0.1416(2) 1.1910(5) 0.16924(18) 0.0560(11) Uani d . 1
C C5 -0.15283(19) 1.0401(5) 0.13275(16) 0.0548(12) Uani d . 1
H H5A -0.1949 1.0646 0.1101 0.066 Uiso calc R 1
H H5B -0.1674 0.9506 0.1567 0.066 Uiso calc R 1
C C6 -0.0940(2) 0.9677(6) 0.09423(16) 0.0572(12) Uani d U 1
C C7 -0.1294(3) 0.8230(7) 0.0635(2) 0.0944(18) Uani d U 1
H H7A -0.0942 0.7747 0.0392 0.142 Uiso calc R 1
H H7B -0.1704 0.8625 0.0429 0.142 Uiso calc R 1
H H7C -0.1455 0.7413 0.0891 0.142 Uiso calc R 1
C C8 -0.0819(4) 1.0926(5) 0.0489(3) 0.0828(19) Uani d U 1
H H8A -0.0515 1.0440 0.0214 0.125 Uiso calc R 1
H H8B -0.1278 1.1241 0.0331 0.125 Uiso calc R 1
H H8C -0.0582 1.1885 0.0635 0.125 Uiso calc R 1
C C9 -0.0281(2) 0.9002(5) 0.12525(16) 0.0516(11) Uani d . 1
C C10 0.0437(2) 0.9350(5) 0.11216(16) 0.0560(12) Uani d . 1
H H10A 0.0537 1.0030 0.0826 0.067 Uiso calc R 1
C C11 0.1009(2) 0.8710(5) 0.14201(17) 0.0517(11) Uani d . 1
C C12 0.0887(2) 0.7707(6) 0.18782(17) 0.0530(11) Uani d . 1
C C13 0.0165(2) 0.7314(5) 0.20028(16) 0.0494(11) Uani d . 1
C C14 -0.0393(2) 0.7926(5) 0.16925(16) 0.0517(11) Uani d . 1
H H14A -0.0869 0.7615 0.1777 0.062 Uiso calc R 1
C C15 0.0000 0.6259(8) 0.2500 0.0642(18) Uani d S 1
H H15A 0.0414 0.5566 0.2574 0.077 Uiso d R 1
C C16 0.2623(2) 0.9836(6) 0.07688(18) 0.0618(12) Uani d . 1
C C17 0.3101(3) 1.0513(7) 0.0388(2) 0.0801(16) Uani d . 1
H H17A 0.2926 1.1063 0.0082 0.096 Uiso calc R 1
C C18 0.3831(3) 1.0345(7) 0.0477(2) 0.0859(17) Uani d . 1
H H18A 0.4159 1.0798 0.0229 0.103 Uiso calc R 1
C C19 0.4096(3) 0.9510(7) 0.0929(2) 0.0847(17) Uani d . 1
H H19A 0.4599 0.9406 0.0971 0.102 Uiso calc R 1
C C20 0.3649(2) 0.8832(6) 0.1319(2) 0.0739(14) Uani d . 1
H H20A 0.3832 0.8288 0.1623 0.089 Uiso calc R 1
C C21 0.2894(2) 0.9016(6) 0.12246(19) 0.0615(13) Uani 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
C12 O1 H1 . 109.5
N2 N1 N3 . 116.6(3)
N2 N1 C11 . 121.5(3)
N3 N1 C11 . 121.9(4)
N1 N2 C16 . 102.3(4)
N1 N3 C21 . 102.8(4)
C4 C1 H1A . 109.5
C4 C1 H1B . 109.5
H1A C1 H1B . 109.5
C4 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C4 C2 H2A . 109.5
C4 C2 H2B . 109.5
H2A C2 H2B . 109.5
C4 C2 H2C . 109.5
H2A C2 H2C . 109.5
H2B C2 H2C . 109.5
C4 C3 H3A . 109.5
C4 C3 H3B . 109.5
H3A C3 H3B . 109.5
C4 C3 H3C . 109.5
H3A C3 H3C . 109.5
H3B C3 H3C . 109.5
C3 C4 C2 . 108.7(4)
C3 C4 C5 . 113.4(3)
C2 C4 C5 . 106.9(4)
C3 C4 C1 . 108.2(4)
C2 C4 C1 . 106.2(4)
C5 C4 C1 . 113.2(4)
C4 C5 C6 . 124.5(3)
C4 C5 H5A . 106.2
C6 C5 H5A . 106.2
C4 C5 H5B . 106.2
C6 C5 H5B . 106.2
H5A C5 H5B . 106.4
C9 C6 C8 . 119.2(4)
C9 C6 C7 . 107.7(4)
C8 C6 C7 . 102.1(4)
C9 C6 C5 . 112.3(3)
C8 C6 C5 . 107.3(4)
C7 C6 C5 . 107.2(4)
C6 C7 H7A . 109.5
C6 C7 H7B . 109.5
H7A C7 H7B . 109.5
C6 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C6 C8 H8A . 109.5
C6 C8 H8B . 109.5
H8A C8 H8B . 109.5
C6 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
C10 C9 C14 . 116.4(4)
C10 C9 C6 . 124.2(4)
C14 C9 C6 . 119.4(4)
C11 C10 C9 . 121.5(4)
C11 C10 H10A . 119.3
C9 C10 H10A . 119.3
C10 C11 C12 . 121.4(4)
C10 C11 N1 . 119.0(4)
C12 C11 N1 . 119.6(4)
O1 C12 C13 . 118.1(4)
O1 C12 C11 . 124.5(4)
C13 C12 C11 . 117.3(4)
C14 C13 C12 . 120.3(4)
C14 C13 C15 . 120.2(3)
C12 C13 C15 . 119.5(3)
C13 C14 C9 . 123.0(4)
C13 C14 H14A . 118.5
C9 C14 H14A . 118.5
C13 C15 C13 3 111.6(5)
C13 C15 H15A 3 109.5
C13 C15 H15A . 108.9
N2 C16 C17 . 130.1(5)
N2 C16 C21 . 109.6(4)
C17 C16 C21 . 120.3(4)
C18 C17 C16 . 118.0(5)
C18 C17 H17A . 121.0
C16 C17 H17A . 121.0
C17 C18 C19 . 121.3(5)
C17 C18 H18A . 119.4
C19 C18 H18A . 119.4
C20 C19 C18 . 123.0(5)
C20 C19 H19A . 118.5
C18 C19 H19A . 118.5
C19 C20 C21 . 115.3(5)
C19 C20 H20A . 122.3
C21 C20 H20A . 122.3
N3 C21 C16 . 108.7(4)
N3 C21 C20 . 129.2(5)
C16 C21 C20 . 122.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C12 . 1.352(4)
O1 H1 . 0.8200
N1 N2 . 1.337(5)
N1 N3 . 1.346(4)
N1 C11 . 1.432(5)
N2 C16 . 1.357(5)
N3 C21 . 1.352(5)
C1 C4 . 1.536(6)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 C4 . 1.528(5)
C2 H2A . 0.9600
C2 H2B . 0.9600
C2 H2C . 0.9600
C3 C4 . 1.519(5)
C3 H3A . 0.9600
C3 H3B . 0.9600
C3 H3C . 0.9600
C4 C5 . 1.530(6)
C5 C6 . 1.548(5)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C9 . 1.527(5)
C6 C8 . 1.520(8)
C6 C7 . 1.537(6)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 C10 . 1.383(5)
C9 C14 . 1.403(5)
C10 C11 . 1.379(5)
C10 H10A . 0.9300
C11 C12 . 1.406(6)
C12 C13 . 1.393(5)
C13 C14 . 1.367(5)
C13 C15 . 1.520(5)
C14 H14A . 0.9300
C15 C13 3 1.520(5)
C15 H15A . 0.9600
C16 C17 . 1.392(6)
C16 C21 . 1.392(6)
C17 C18 . 1.361(6)
C17 H17A . 0.9300
C18 C19 . 1.388(7)
C18 H18A . 0.9300
C19 C20 . 1.373(6)
C19 H19A . 0.9300
C20 C21 . 1.409(5)
C20 H20A . 0.9300
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 N3 0.82 1.87 2.596(5) 146
O1 H1 N1 0.82 2.46 2.883(5) 113
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
N3 N1 N2 C16 . 0.3(5)
C11 N1 N2 C16 . -178.1(4)
N2 N1 N3 C21 . -0.2(5)
C11 N1 N3 C21 . 178.2(4)
C3 C4 C5 C6 . -47.8(6)
C2 C4 C5 C6 . -167.6(4)
C1 C4 C5 C6 . 75.9(5)
C4 C5 C6 C9 . 64.5(5)
C4 C5 C6 C8 . -68.3(5)
C4 C5 C6 C7 . -177.3(4)
C8 C6 C9 C10 . -5.4(6)
C7 C6 C9 C10 . 110.1(5)
C5 C6 C9 C10 . -132.1(4)
C8 C6 C9 C14 . 176.2(4)
C7 C6 C9 C14 . -68.3(5)
C5 C6 C9 C14 . 49.5(5)
C14 C9 C10 C11 . -2.0(6)
C6 C9 C10 C11 . 179.6(4)
C9 C10 C11 C12 . -1.5(6)
C9 C10 C11 N1 . 176.4(4)
N2 N1 C11 C10 . -4.4(6)
N3 N1 C11 C10 . 177.3(4)
N2 N1 C11 C12 . 173.5(4)
N3 N1 C11 C12 . -4.8(6)
C10 C11 C12 O1 . -178.2(4)
N1 C11 C12 O1 . 4.0(6)
C10 C11 C12 C13 . 3.2(6)
N1 C11 C12 C13 . -174.7(4)
O1 C12 C13 C14 . 179.9(4)
C11 C12 C13 C14 . -1.4(6)
O1 C12 C13 C15 . 2.4(6)
C11 C12 C13 C15 . -178.9(4)
C12 C13 C14 C9 . -2.2(6)
C15 C13 C14 C9 . 175.3(4)
C10 C9 C14 C13 . 3.8(6)
C6 C9 C14 C13 . -177.6(4)
C14 C13 C15 C13 3 -83.6(4)
C12 C13 C15 C13 3 93.9(4)
N1 N2 C16 C17 . -179.0(5)
N1 N2 C16 C21 . -0.2(5)
N2 C16 C17 C18 . 178.7(5)
C21 C16 C17 C18 . 0.0(8)
C16 C17 C18 C19 . 0.7(8)
C17 C18 C19 C20 . -1.2(9)
C18 C19 C20 C21 . 0.9(8)
N1 N3 C21 C16 . 0.1(5)
N1 N3 C21 C20 . 179.3(5)
N2 C16 C21 N3 . 0.1(6)
C17 C16 C21 N3 . 179.1(4)
N2 C16 C21 C20 . -179.2(4)
C17 C16 C21 C20 . -0.2(7)
C19 C20 C21 N3 . -179.3(5)
C19 C20 C21 C16 . -0.2(7)
