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#$Date: 2022-03-18 09:36:54 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273778 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104778.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_8104778
loop_
_publ_author_name
'Zhang, Weilian'
'Zuo, Zhenyu'
'Yanhui, Chen'
'Bin, Liu'
_publ_section_title
;
 The crystal structure of
 (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one,
 C24H24N2O3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              601
_journal_page_last               603
_journal_paper_doi               10.1515/ncrs-2021-0022
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C24 H24 N2 O3'
_chemical_formula_sum            'C24 H24 N2 O3'
_chemical_formula_weight         388.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 106.728(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.674(3)
_cell_length_b                   7.3900(14)
_cell_length_c                   20.862(4)
_cell_measurement_reflns_used    1500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.432
_cell_measurement_theta_min      2.543
_cell_volume                     2018.9(7)
_computing_cell_refinement       'SAINT (Brucker, 2012)[2]'
_computing_data_collection       'APEX2 (Brucker, 2012)[2]'
_computing_data_reduction        'SAINT (Brucker, 2012)[2]'
_computing_molecular_graphics    'Diamond 4.0[4]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13143
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.595
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0633
_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)+(0.0952P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1844
_reflns_number_total             3530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0022_suppl.cif
_cod_data_source_block           m
_cod_database_code               8104778
_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   0.983
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), N2(H2A)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.6986(2) 0.4610(4) 0.33550(15) 0.0508(8) Uani 1 1 d . . . . .
C2 C 0.7324(3) 0.4662(4) 0.40478(16) 0.0614(9) Uani 1 1 d . . . . .
H2 H 0.6850 0.4717 0.4289 0.074 Uiso 1 1 calc R . . . .
C3 C 0.8348(3) 0.4635(5) 0.43842(17) 0.0703(10) Uani 1 1 d . . . . .
H3 H 0.8558 0.4685 0.4849 0.084 Uiso 1 1 calc R . . . .
C4 C 0.9066(3) 0.4535(5) 0.40386(18) 0.0737(10) Uani 1 1 d . . . . .
H4 H 0.9758 0.4515 0.4269 0.088 Uiso 1 1 calc R . . . .
C5 C 0.8746(2) 0.4462(5) 0.33398(17) 0.0655(10) Uani 1 1 d . . . . .
H5 H 0.9222 0.4378 0.3100 0.079 Uiso 1 1 calc R . . . .
C6 C 0.7722(2) 0.4516(4) 0.30107(15) 0.0516(8) Uani 1 1 d . . . . .
C7 C 0.7976(2) 0.4539(5) 0.19064(14) 0.0549(8) Uani 1 1 d . . . . .
H7A H 0.8390 0.3451 0.1967 0.066 Uiso 1 1 calc R . . . .
H7B H 0.8423 0.5586 0.2002 0.066 Uiso 1 1 calc R . . . .
C8 C 0.7259(2) 0.4633(4) 0.12108(14) 0.0537(8) Uani 1 1 d . . . . .
H8A H 0.6749 0.3685 0.1145 0.064 Uiso 1 1 calc R . . . .
H8B H 0.6913 0.5794 0.1138 0.064 Uiso 1 1 calc R . . . .
C9 C 0.7329(2) 0.4139(4) 0.00945(15) 0.0508(8) Uani 1 1 d . . . . .
C10 C 0.6318(2) 0.4615(5) -0.01889(16) 0.0598(9) Uani 1 1 d . . . . .
H10 H 0.5954 0.5170 0.0070 0.072 Uiso 1 1 calc R . . . .
C11 C 0.5851(2) 0.4265(5) -0.08572(17) 0.0652(10) Uani 1 1 d . . . . .
H11 H 0.5171 0.4585 -0.1046 0.078 Uiso 1 1 calc R . . . .
C12 C 0.6382(2) 0.3447(4) -0.12453(16) 0.0632(9) Uani 1 1 d . . . . .
H12 H 0.6059 0.3206 -0.1694 0.076 Uiso 1 1 calc R . . . .
C13 C 0.7390(2) 0.2982(4) -0.09730(15) 0.0557(8) Uani 1 1 d . . . . .
H13 H 0.7743 0.2425 -0.1239 0.067 Uiso 1 1 calc R . . . .
C14 C 0.7884(2) 0.3334(4) -0.03082(15) 0.0459(7) Uani 1 1 d . . . . .
C15 C 0.9706(2) 0.3223(4) -0.08844(14) 0.0567(9) Uani 1 1 d . . . . .
H15A H 1.0372 0.3589 -0.0901 0.085 Uiso 1 1 calc GR . . . .
H15B H 0.9231 0.4193 -0.1041 0.085 Uiso 1 1 calc GR . . . .
H15C H 0.9491 0.2180 -0.1164 0.085 Uiso 1 1 calc GR . . . .
C16 C 0.9745(2) 0.2762(4) -0.01741(14) 0.0445(7) Uani 1 1 d . . . . .
C17 C 1.0673(2) 0.2308(4) 0.02690(14) 0.0483(8) Uani 1 1 d . . . . .
H17 H 1.1241 0.2295 0.0109 0.058 Uiso 1 1 calc R . . . .
C18 C 1.0824(2) 0.1860(4) 0.09499(15) 0.0470(8) Uani 1 1 d . . . . .
C19 C 1.1877(2) 0.1466(4) 0.14006(15) 0.0465(8) Uani 1 1 d . . . . .
C20 C 1.2758(2) 0.1954(4) 0.12423(16) 0.0588(9) Uani 1 1 d . . . . .
H20 H 1.2710 0.2508 0.0834 0.071 Uiso 1 1 calc R . . . .
C21 C 1.3707(3) 0.1622(5) 0.16862(18) 0.0717(10) Uani 1 1 d . . . . .
H21 H 1.4294 0.1960 0.1577 0.086 Uiso 1 1 calc R . . . .
C22 C 1.3785(3) 0.0790(5) 0.22905(18) 0.0719(10) Uani 1 1 d . . . . .
H22 H 1.4423 0.0571 0.2590 0.086 Uiso 1 1 calc R . . . .
C23 C 1.2914(3) 0.0287(4) 0.24488(16) 0.0622(9) Uani 1 1 d . . . . .
H23 H 1.2965 -0.0286 0.2854 0.075 Uiso 1 1 calc R . . . .
C24 C 1.1973(3) 0.0624(4) 0.20133(15) 0.0550(8) Uani 1 1 d . . . . .
H24 H 1.1390 0.0287 0.2128 0.066 Uiso 1 1 calc R . . . .
N1 N 0.5959(2) 0.4638(4) 0.29936(14) 0.0720(9) Uani 1 1 d . . . . .
H1A H 0.5756 0.3541 0.2902 0.086 Uiso 1 1 d GR . . . .
H1B H 0.5613 0.5132 0.3232 0.086 Uiso 1 1 d GR . . . .
N2 N 0.89046(18) 0.2845(3) 0.00320(12) 0.0500(7) Uani 1 1 d . . . . .
H2A H 0.9001 0.2550 0.0444 0.060 Uiso 1 1 calc R . . . .
O1 O 0.73090(15) 0.4513(3) 0.23229(10) 0.0643(7) Uani 1 1 d . . . . .
O2 O 0.78584(14) 0.4406(3) 0.07565(9) 0.0585(6) Uani 1 1 d . . . . .
O3 O 1.00963(16) 0.1834(3) 0.12094(10) 0.0664(7) 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 117.6(3) . .
C2 C1 N1 123.2(3) . .
N1 C1 C6 119.2(3) . .
C1 C2 H2 119.4 . .
C3 C2 C1 121.2(3) . .
C3 C2 H2 119.4 . .
C2 C3 H3 119.7 . .
C2 C3 C4 120.6(3) . .
C4 C3 H3 119.7 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.4(3) . .
C5 C4 H4 120.3 . .
C4 C5 H5 120.3 . .
C6 C5 C4 119.3(3) . .
C6 C5 H5 120.3 . .
C5 C6 C1 121.8(3) . .
C5 C6 O1 125.0(3) . .
O1 C6 C1 113.2(3) . .
H7A C7 H7B 109.0 . .
C8 C7 H7A 111.0 . .
C8 C7 H7B 111.0 . .
O1 C7 H7A 111.0 . .
O1 C7 H7B 111.0 . .
O1 C7 C8 103.6(2) . .
C7 C8 H8A 110.3 . .
C7 C8 H8B 110.3 . .
H8A C8 H8B 108.5 . .
O2 C8 C7 107.2(2) . .
O2 C8 H8A 110.3 . .
O2 C8 H8B 110.3 . .
C10 C9 C14 119.6(3) . .
O2 C9 C10 124.4(3) . .
O2 C9 C14 116.0(3) . .
C9 C10 H10 120.0 . .
C11 C10 C9 120.0(3) . .
C11 C10 H10 120.0 . .
C10 C11 H11 119.7 . .
C12 C11 C10 120.5(3) . .
C12 C11 H11 119.7 . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.2(3) . .
C13 C12 H12 119.9 . .
C12 C13 H13 119.7 . .
C12 C13 C14 120.7(3) . .
C14 C13 H13 119.7 . .
C9 C14 N2 115.4(3) . .
C13 C14 C9 119.0(3) . .
C13 C14 N2 125.5(3) . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C16 C15 H15A 109.5 . .
C16 C15 H15B 109.5 . .
C16 C15 H15C 109.5 . .
C17 C16 C15 118.7(2) . .
N2 C16 C15 121.0(3) . .
N2 C16 C17 120.3(3) . .
C16 C17 H17 117.6 . .
C16 C17 C18 124.7(3) . .
C18 C17 H17 117.6 . .
C17 C18 C19 120.6(3) . .
O3 C18 C17 122.0(3) . .
O3 C18 C19 117.4(3) . .
C20 C19 C18 122.8(3) . .
C20 C19 C24 118.4(3) . .
C24 C19 C18 118.7(3) . .
C19 C20 H20 119.8 . .
C21 C20 C19 120.5(3) . .
C21 C20 H20 119.8 . .
C20 C21 H21 119.9 . .
C22 C21 C20 120.1(3) . .
C22 C21 H21 119.9 . .
C21 C22 H22 120.1 . .
C23 C22 C21 119.7(3) . .
C23 C22 H22 120.1 . .
C22 C23 H23 119.8 . .
C24 C23 C22 120.3(3) . .
C24 C23 H23 119.8 . .
C19 C24 H24 119.6 . .
C23 C24 C19 120.9(3) . .
C23 C24 H24 119.6 . .
C1 N1 H1A 108.5 . .
C1 N1 H1B 109.3 . .
H1A N1 H1B 109.4 . .
C14 N2 H2A 114.2 . .
C16 N2 C14 131.5(2) . .
C16 N2 H2A 114.2 . .
C6 O1 C7 119.3(2) . .
C9 O2 C8 116.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.385(4) .
C1 C6 1.397(4) .
C1 N1 1.390(4) .
C2 H2 0.9300 .
C2 C3 1.373(5) .
C3 H3 0.9300 .
C3 C4 1.378(4) .
C4 H4 0.9300 .
C4 C5 1.397(4) .
C5 H5 0.9300 .
C5 C6 1.371(4) .
C6 O1 1.383(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.501(4) .
C7 O1 1.430(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 O2 1.430(3) .
C9 C10 1.383(4) .
C9 C14 1.415(4) .
C9 O2 1.376(3) .
C10 H10 0.9300 .
C10 C11 1.381(4) .
C11 H11 0.9300 .
C11 C12 1.374(4) .
C12 H12 0.9300 .
C12 C13 1.374(4) .
C13 H13 0.9300 .
C13 C14 1.381(4) .
C14 N2 1.418(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C15 C16 1.506(4) .
C16 C17 1.379(4) .
C16 N2 1.340(3) .
C17 H17 0.9300 .
C17 C18 1.415(4) .
C18 C19 1.504(4) .
C18 O3 1.262(3) .
C19 C20 1.385(4) .
C19 C24 1.393(4) .
C20 H20 0.9300 .
C20 C21 1.382(4) .
C21 H21 0.9300 .
C21 C22 1.379(4) .
C22 H22 0.9300 .
C22 C23 1.375(4) .
C23 H23 0.9300 .
C23 C24 1.368(4) .
C24 H24 0.9300 .
N1 H1A 0.8601 .
N1 H1B 0.8601 .
N2 H2A 0.8600 .
