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#$Date: 2022-02-09 12:44:24 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272883 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104563.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_8104563
loop_
_publ_author_name
'Orang-o, Daniel M.'
'Onani, Martin O.'
'Tarus, Paul K.'
'Lutta, Samuel T.'
'Lalancette, Roger A.'
_publ_section_title
;
 Crystal structure of
 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol),
 C20H24N2O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1191
_journal_page_last               1193
_journal_paper_doi               10.1515/ncrs-2021-0273
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C20 H24 N2 O4'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 104.271(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0474(3)
_cell_length_b                   6.0853(2)
_cell_length_c                   13.9881(4)
_cell_measurement_reflns_used    6667
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.26
_cell_volume                     911.36(5)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      99.94
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9785
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.629
_diffrn_reflns_theta_max         66.629
_diffrn_reflns_theta_min         3.260
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0290
_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)+(0.0414P)²+0.1013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2539
_reflns_number_total             2698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0273_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        911.35(5)
_cod_database_code               8104563
_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.
;
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.782
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.64008(17) 0.9164(4) 0.13709(13) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.57652(17) 1.1180(4) 0.12601(13) 0.0184(5) Uani 1 1 d . . . . .
C3 C 0.59650(18) 1.2685(4) 0.05643(14) 0.0207(4) Uani 1 1 d . . . . .
H3A H 0.553564 1.405082 0.048317 0.025 Uiso 1 1 calc R . . . .
C4 C 0.67834(18) 1.2199(4) -0.00069(14) 0.0221(5) Uani 1 1 d . . . . .
H4 H 0.690968 1.323514 -0.048090 0.027 Uiso 1 1 calc R . . . .
C5 C 0.74297(18) 1.0207(4) 0.01003(14) 0.0199(5) Uani 1 1 d . . . . .
C6 C 0.72360(17) 0.8693(4) 0.07859(14) 0.0181(5) Uani 1 1 d . . . . .
H6 H 0.766908 0.733040 0.086129 0.022 Uiso 1 1 calc R . . . .
C7 C 0.8705(2) 0.7766(4) -0.05657(15) 0.0302(5) Uani 1 1 d . . . . .
H7A H 0.920348 0.730498 0.008381 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.923010 0.776059 -0.103758 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.800605 0.674659 -0.078953 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.61923(16) 0.7529(4) 0.20764(13) 0.0160(4) Uani 1 1 d . . . . .
H8 H 0.660896 0.615342 0.212042 0.019 Uiso 1 1 calc R . . . .
C9 C 0.52678(18) 0.6169(4) 0.33066(14) 0.0201(5) Uani 1 1 d . . . . .
H9A H 0.555757 0.668093 0.399719 0.024 Uiso 1 1 calc R . . . .
H9B H 0.577009 0.486794 0.322409 0.024 Uiso 1 1 calc R . . . .
C10 C 0.39022(17) 0.5529(4) 0.31019(14) 0.0194(5) Uani 1 1 d . . . . .
H10A H 0.361685 0.500408 0.241300 0.023 Uiso 1 1 calc R . . . .
H10B H 0.340043 0.683757 0.317511 0.023 Uiso 1 1 calc R . . . .
C11 C 0.36864(17) 0.3739(4) 0.37980(14) 0.0199(5) Uani 1 1 d . . . . .
H11A H 0.393288 0.428978 0.448467 0.024 Uiso 1 1 calc R . . . .
H11B H 0.421949 0.245726 0.374869 0.024 Uiso 1 1 calc R . . . .
C12 C 0.23267(17) 0.3020(4) 0.35600(14) 0.0230(5) Uani 1 1 d . . . . .
H12A H 0.178671 0.431631 0.356440 0.028 Uiso 1 1 calc R . . . .
H12B H 0.209525 0.236698 0.289134 0.028 Uiso 1 1 calc R . . . .
C13 C 0.15127(16) 0.2041(4) 0.49011(14) 0.0182(5) Uani 1 1 d . . . . .
H13 H 0.115172 0.346668 0.483727 0.022 Uiso 1 1 calc R . . . .
C14 C 0.13610(16) 0.0626(4) 0.57031(13) 0.0166(4) Uani 1 1 d . . . . .
C15 C 0.18869(17) -0.1481(4) 0.58234(14) 0.0179(5) Uani 1 1 d . . . . .
C16 C 0.18253(17) -0.2721(4) 0.66495(13) 0.0192(5) Uani 1 1 d . . . . .
H16 H 0.218728 -0.414604 0.673975 0.023 Uiso 1 1 calc R . . . .
C17 C 0.12403(17) -0.1884(4) 0.73355(14) 0.0192(5) Uani 1 1 d . . . . .
H17 H 0.121833 -0.272869 0.790210 0.023 Uiso 1 1 calc R . . . .
C18 C 0.06823(17) 0.0180(4) 0.72087(14) 0.0179(4) Uani 1 1 d . . . . .
C19 C 0.07448(16) 0.1445(4) 0.63968(13) 0.0171(4) Uani 1 1 d . . . . .
H19 H 0.037210 0.286097 0.630955 0.021 Uiso 1 1 calc R . . . .
C20 C -0.05252(18) 0.2871(4) 0.78128(15) 0.0239(5) Uani 1 1 d . . . . .
H20A H 0.009102 0.405347 0.787026 0.036 Uiso 1 1 calc GR . . . .
H20B H -0.098280 0.304664 0.832568 0.036 Uiso 1 1 calc GR . . . .
H20C H -0.111223 0.293737 0.716170 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.54579(14) 0.7912(3) 0.26385(11) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.21211(14) 0.1411(3) 0.42787(11) 0.0201(4) Uani 1 1 d . . . . .
O1 O 0.49423(13) 1.1699(3) 0.18013(10) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.490835 1.066750 0.219273 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.82349(13) 0.9927(3) -0.04984(10) 0.0266(4) Uani 1 1 d . . . . .
O3 O 0.24919(12) -0.2351(3) 0.51775(9) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.250825 -0.142609 0.473486 0.033 Uiso 1 1 calc GR . . . .
O4 O 0.00990(12) 0.0797(3) 0.79304(9) 0.0215(4) 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
C18 O4 C20 117.16(16) . .
C15 O3 H3 109.5 . .
C2 O1 H1 109.5 . .
C5 O2 C7 117.13(17) . .
C8 N1 C9 118.17(19) . .
C13 N2 C12 117.62(19) . .
O1 C2 C1 121.89(18) . .
O1 C2 C3 118.70(19) . .
C3 C2 C1 119.40(18) . .
O3 C15 C16 118.23(19) . .
O3 C15 C14 122.33(18) . .
C16 C15 C14 119.41(18) . .
C15 C16 H16 119.9 . .
C17 C16 C15 120.2(2) . .
C17 C16 H16 119.9 . .
C15 C14 C19 119.88(18) . .
C15 C14 C13 120.71(17) . .
C19 C14 C13 119.29(19) . .
H10A C10 H10B 107.9 . .
C9 C10 H10A 109.3 . .
C9 C10 H10B 109.3 . .
C9 C10 C11 111.69(15) . .
C11 C10 H10A 109.3 . .
C11 C10 H10B 109.3 . .
O4 C18 C17 115.18(17) . .
O4 C18 C19 125.1(2) . .
C19 C18 C17 119.68(18) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C5 C6 C1 120.2(2) . .
N1 C8 H8 119.3 . .
N1 C8 C1 121.3(2) . .
C1 C8 H8 119.3 . .
C16 C17 C18 120.90(19) . .
C16 C17 H17 119.5 . .
C18 C17 H17 119.5 . .
N1 C9 C10 111.03(16) . .
N1 C9 H9A 109.4 . .
N1 C9 H9B 109.4 . .
C10 C9 H9A 109.4 . .
C10 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C3 C4 C5 121.02(19) . .
C14 C19 H19 120.1 . .
C18 C19 C14 119.9(2) . .
C18 C19 H19 120.1 . .
C2 C1 C6 119.76(19) . .
C2 C1 C8 120.85(17) . .
C6 C1 C8 119.38(19) . .
O2 C5 C6 125.0(2) . .
O2 C5 C4 115.66(18) . .
C6 C5 C4 119.34(18) . .
N2 C13 C14 121.7(2) . .
N2 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C10 C11 H11A 109.3 . .
C10 C11 H11B 109.3 . .
C10 C11 C12 111.64(15) . .
H11A C11 H11B 108.0 . .
C12 C11 H11A 109.3 . .
C12 C11 H11B 109.3 . .
N2 C12 C11 110.80(15) . .
N2 C12 H12A 109.5 . .
N2 C12 H12B 109.5 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
O4 C20 H20A 109.5 . .
O4 C20 H20B 109.5 . .
O4 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C2 C3 H3A 119.9 . .
C4 C3 C2 120.2(2) . .
C4 C3 H3A 119.9 . .
O2 C7 H7A 109.5 . .
O2 C7 H7B 109.5 . .
O2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C18 1.377(2) .
O4 C20 1.428(3) .
O3 H3 0.8400 .
O3 C15 1.357(2) .
O1 H1 0.8400 .
O1 C2 1.356(2) .
O2 C5 1.374(2) .
O2 C7 1.425(3) .
N1 C8 1.283(2) .
N1 C9 1.462(3) .
N2 C13 1.283(2) .
N2 C12 1.461(3) .
C2 C1 1.403(3) .
C2 C3 1.393(3) .
C15 C16 1.396(3) .
C15 C14 1.401(3) .
C16 H16 0.9500 .
C16 C17 1.380(3) .
C14 C19 1.407(3) .
C14 C13 1.456(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C9 1.516(3) .
C10 C11 1.518(3) .
C18 C17 1.391(3) .
C18 C19 1.388(3) .
C6 H6 0.9500 .
C6 C1 1.405(3) .
C6 C5 1.384(3) .
C8 H8 0.9500 .
C8 C1 1.459(3) .
C17 H17 0.9500 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C4 H4 0.9500 .
C4 C5 1.396(3) .
C4 C3 1.378(3) .
C19 H19 0.9500 .
C13 H13 0.9500 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.521(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C3 H3A 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(3)
