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#$Date: 2022-05-13 11:10:13 +0300 (Fri, 13 May 2022) $
#$Revision: 275399 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105244.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105244
loop_
_publ_author_name
'Mu, Hao-Ran'
'Wang, Ji-Fa'
'Bian, Ruo-Nan'
'Dong, Wen-Kui'
_publ_section_title
;
 Synthesis and crystal structure of
 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol,
 C35H40N4O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              643
_journal_page_last               644
_journal_paper_doi               10.1515/ncrs-2019-0876
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C35 H40 N4 O4'
_chemical_formula_sum            'C35 H40 N4 O4'
_chemical_formula_weight         580.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 101.2260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.1768(5)
_cell_length_b                   6.07340(10)
_cell_length_c                   18.0123(3)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.09
_cell_volume                     3130.75(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18294
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.629
_diffrn_reflns_theta_max         66.629
_diffrn_reflns_theta_min         3.088
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0422
_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)+(0.0623P)²+1.0672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2482
_reflns_number_total             2709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0876_suppl.cif
_cod_data_source_block           1125
_cod_database_code               8105244
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H18a(0.5) H18b(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C17(H17a,H17b)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C16(H16), C9(H9), C6(H6), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C14(H14a,H14b,H14c), C13(H13a,H13b,H13c)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39892(4) 0.4416(2) 0.53835(7) 0.0453(3) Uani 1 1 d . . . . .
C2 C 0.38236(4) 0.3907(2) 0.60505(7) 0.0457(3) Uani 1 1 d . . . . .
C3 C 0.34892(4) 0.5263(2) 0.62737(7) 0.0482(3) Uani 1 1 d . . . . .
H3 H 0.3377 0.4919 0.6709 0.058 Uiso 1 1 calc R . . . .
C4 C 0.33210(4) 0.7107(2) 0.58607(7) 0.0456(3) Uani 1 1 d . . . . .
C5 C 0.29794(4) 0.8609(2) 0.61092(7) 0.0465(3) Uani 1 1 d . . . . .
C6 C 0.29737(5) 0.8954(3) 0.68718(8) 0.0575(4) Uani 1 1 d . . . . .
H6 H 0.3186 0.8225 0.7243 0.069 Uiso 1 1 calc R . . . .
C7 C 0.26520(6) 1.0379(3) 0.70718(9) 0.0653(4) Uani 1 1 d . . . . .
H7 H 0.2657 1.0578 0.7585 0.078 Uiso 1 1 calc R . . . .
C8 C 0.23380(5) 1.1140(2) 0.58538(9) 0.0603(4) Uani 1 1 d . . . . .
H8 H 0.2117 1.1870 0.5496 0.072 Uiso 1 1 calc R . . . .
C9 C 0.26479(5) 0.9764(2) 0.55970(8) 0.0529(3) Uani 1 1 d . . . . .
H9 H 0.2635 0.9606 0.5080 0.064 Uiso 1 1 calc R . . . .
C10 C 0.34871(4) 0.7538(2) 0.51960(7) 0.0465(3) Uani 1 1 d . . . . .
H10 H 0.3371 0.8766 0.4912 0.056 Uiso 1 1 calc R . . . .
C11 C 0.38145(4) 0.6243(2) 0.49367(7) 0.0449(3) Uani 1 1 d . . . . .
C12 C 0.39878(5) 0.6822(2) 0.42044(8) 0.0524(3) Uani 1 1 d . . . . .
C13 C 0.37181(7) 0.8771(3) 0.38017(10) 0.0750(5) Uani 1 1 d . . . . .
H13A H 0.3393 0.8392 0.3658 0.113 Uiso 1 1 calc GR . . . .
H13B H 0.3839 0.9131 0.3358 0.113 Uiso 1 1 calc GR . . . .
H13C H 0.3752 1.0017 0.4136 0.113 Uiso 1 1 calc GR . . . .
C14 C 0.39199(6) 0.4863(3) 0.36524(8) 0.0666(4) Uani 1 1 d . . . . .
H14A H 0.4119 0.3672 0.3865 0.100 Uiso 1 1 calc GR . . . .
H14B H 0.3998 0.5304 0.3181 0.100 Uiso 1 1 calc GR . . . .
H14C H 0.3600 0.4390 0.3568 0.100 Uiso 1 1 calc GR . . . .
C15 C 0.45065(6) 0.7452(3) 0.43996(11) 0.0749(5) Uani 1 1 d . . . . .
H15A H 0.4545 0.8723 0.4722 0.112 Uiso 1 1 calc GR . . . .
H15B H 0.4616 0.7780 0.3943 0.112 Uiso 1 1 calc GR . . . .
H15C H 0.4683 0.6247 0.4656 0.112 Uiso 1 1 calc GR . . . .
C16 C 0.39993(5) 0.2041(2) 0.65300(7) 0.0506(3) Uani 1 1 d . . . . .
H16 H 0.3863 0.1724 0.6943 0.061 Uiso 1 1 calc R . . . .
C17 C 0.48253(5) -0.2113(2) 0.68031(8) 0.0539(3) Uani 1 1 d . . . . .
H17A H 0.5072 -0.1170 0.6695 0.065 Uiso 1 1 calc R . . . .
H17B H 0.4721 -0.3065 0.6371 0.065 Uiso 1 1 calc R . . . .
C18 C 0.5000 -0.3467(3) 0.7500 0.0522(4) Uani 1 2 d S T P . .
H18A H 0.4749 -0.4410 0.7593 0.063 Uiso 0.5 1 calc R . . . .
H18B H 0.5251 -0.4410 0.7407 0.063 Uiso 0.5 1 calc R . . . .
N1 N 0.43319(4) 0.08274(19) 0.64063(6) 0.0533(3) Uani 1 1 d . . . . .
N2 N 0.23342(5) 1.1494(2) 0.65847(8) 0.0659(4) Uani 1 1 d . . . . .
O1 O 0.43238(3) 0.31595(17) 0.51712(6) 0.0596(3) Uani 1 1 d . . . . .
H1 H 0.4411 0.2220 0.5495 0.089 Uiso 1 1 calc GR . . . .
O2 O 0.44436(3) -0.08124(17) 0.69532(6) 0.0620(3) Uani 1 1 d . . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 O2 C17 110.11(10) . .
C16 N1 O2 111.81(11) . .
C7 N2 C8 115.43(13) . .
C10 C11 C1 116.83(11) . .
C10 C11 C12 121.37(11) . .
C1 C11 C12 121.78(11) . .
C11 C10 C4 123.86(12) . .
C4 C3 C2 121.25(12) . .
O1 C1 C11 119.00(11) . .
O1 C1 C2 120.13(11) . .
C11 C1 C2 120.87(12) . .
C9 C5 C4 122.13(12) . .
C9 C5 C6 116.01(12) . .
C6 C5 C4 121.86(12) . .
C3 C2 C1 119.33(11) . .
C3 C2 C16 118.28(11) . .
C1 C2 C16 122.37(12) . .
C10 C4 C5 120.48(11) . .
C3 C4 C10 117.81(12) . .
C3 C4 C5 121.71(11) . .
C17 C18 C17 113.72(16) 2_656 .
N1 C16 C2 122.64(12) . .
C15 C12 C11 109.52(12) . .
C15 C12 C14 109.77(13) . .
C14 C12 C11 110.71(11) . .
C13 C12 C11 111.05(11) . .
C13 C12 C15 108.09(13) . .
C13 C12 C14 107.65(13) . .
C8 C9 C5 120.09(13) . .
O2 C17 C18 107.07(10) . .
C7 C6 C5 119.51(14) . .
N2 C7 C6 124.82(14) . .
N2 C8 C9 124.13(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3520(15) .
O2 N1 1.3941(14) .
O2 C17 1.4333(17) .
N1 C16 1.2725(18) .
N2 C7 1.331(2) .
N2 C8 1.336(2) .
C11 C10 1.3867(18) .
C11 C1 1.4064(18) .
C11 C12 1.5425(17) .
C10 C4 1.4012(18) .
C3 C2 1.3947(18) .
C3 C4 1.3804(18) .
C1 C2 1.4136(18) .
C5 C4 1.4832(18) .
C5 C9 1.3897(19) .
C5 C6 1.3928(19) .
C2 C16 1.4563(18) .
C18 C17 1.5041(17) 2_656
C18 C17 1.5041(17) .
C12 C15 1.534(2) .
C12 C14 1.539(2) .
C12 C13 1.524(2) .
C9 C8 1.376(2) .
C6 C7 1.375(2) .
