#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230415.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_2230415
loop_
_publ_author_name
'Pastrán, Jesús'
'Ramírez, Andrea'
'Agrifoglio, Giuseppe'
'Linden, Anthony'
'Dorta, Romano'
_publ_section_title
;
 (Z)-4-(2,5-Di-tert-butylanilino)pent-3-en-2-one
;
_journal_coeditor_code           LH5243
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1405
_journal_page_last               o1406
_journal_paper_doi               10.1107/S1600536811017296
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H29 N O'
_chemical_formula_moiety         'C19 H29 N O'
_chemical_formula_sum            'C19 H29 N O'
_chemical_formula_weight         287.44
_chemical_melting_point          326
_chemical_name_systematic
;
(Z)-4-(2,5-Di-tert-butylanilino)pent-3-en-2-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.6308(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.7759(5)
_cell_length_b                   9.0517(2)
_cell_length_c                   19.3760(4)
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     3588.11(14)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24643
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0643
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.170
_refine_ls_extinction_coef       0.0053(10)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0560P)²+2.1259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                2769
_reflns_number_total             3153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5243.cif
_cod_data_source_block           I
_cod_original_cell_volume        3588.11(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230415
_cod_database_fobs_code          2230415
loop_
_symmetry_equiv_pos_as_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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O18 0.19853(5) 0.78576(13) 0.11732(6) 0.0523(3) Uani d . 1 1 . .
N N15 0.30334(6) 0.85624(13) 0.25496(6) 0.0337(3) Uani d . 1 1 . .
H H15 0.2706(8) 0.7964(19) 0.2197(10) 0.048(4) Uiso d . 1 1 . .
C C1 0.35235(6) 0.80923(15) 0.33326(7) 0.0310(3) Uani d . 1 1 . .
C C2 0.39376(6) 0.68963(14) 0.34376(7) 0.0313(3) Uani d . 1 1 . .
C C3 0.43787(7) 0.65278(16) 0.42337(8) 0.0391(3) Uani d . 1 1 . .
H H3 0.4668 0.5722 0.4339 0.047 Uiso calc R 1 1 . .
C C4 0.44166(7) 0.72794(17) 0.48796(8) 0.0423(4) Uani d . 1 1 . .
H H4 0.4732 0.6982 0.5409 0.051 Uiso calc R 1 1 . .
C C5 0.40051(7) 0.84563(15) 0.47720(8) 0.0361(3) Uani d . 1 1 . .
C C6 0.35575(6) 0.88316(15) 0.39810(8) 0.0347(3) Uani d . 1 1 . .
H H6 0.3264 0.9625 0.3880 0.042 Uiso calc R 1 1 . .
C C7 0.39271(6) 0.60546(15) 0.27398(7) 0.0341(3) Uani d . 1 1 . .
C C8 0.40461(8) 0.71202(17) 0.22106(9) 0.0430(4) Uani d . 1 1 . .
H H81 0.4100 0.6554 0.1817 0.065 Uiso calc R 1 1 . .
H H82 0.4442 0.7699 0.2547 0.065 Uiso calc R 1 1 . .
H H83 0.3672 0.7788 0.1930 0.065 Uiso calc R 1 1 . .
C C9 0.32752(7) 0.52365(16) 0.22340(9) 0.0435(4) Uani d . 1 1 . .
H H91 0.3193 0.4603 0.2583 0.065 Uiso calc R 1 1 . .
H H92 0.3297 0.4628 0.1830 0.065 Uiso calc R 1 1 . .
H H93 0.2920 0.5957 0.1966 0.065 Uiso calc R 1 1 . .
C C10 0.44656(7) 0.48728(17) 0.30488(9) 0.0445(4) Uani d . 1 1 . .
H H101 0.4396 0.4153 0.3376 0.067 Uiso calc R 1 1 . .
H H102 0.4893 0.5344 0.3375 0.067 Uiso calc R 1 1 . .
H H103 0.4451 0.4368 0.2592 0.067 Uiso calc R 1 1 . .
C C11 0.40414(7) 0.93389(17) 0.54685(8) 0.0424(4) Uani d . 1 1 . .
C C12 0.43769(11) 0.8466(2) 0.62528(9) 0.0662(5) Uani d . 1 1 . .
H H121 0.4138 0.7544 0.6185 0.099 Uiso calc R 1 1 . .
H H122 0.4382 0.9056 0.6680 0.099 Uiso calc R 1 1 . .
H H123 0.4827 0.8237 0.6397 0.099 Uiso calc R 1 1 . .
C C13 0.44427(9) 1.0737(2) 0.55784(11) 0.0596(5) Uani d . 1 1 . .
H H131 0.4880 1.0459 0.5692 0.089 Uiso calc R 1 1 . .
H H132 0.4480 1.1316 0.6027 0.089 Uiso calc R 1 1 . .
H H133 0.4225 1.1330 0.5087 0.089 Uiso calc R 1 1 . .
C C14 0.33608(8) 0.9797(2) 0.52823(10) 0.0636(5) Uani d . 1 1 . .
H H141 0.3165 1.0458 0.4817 0.095 Uiso calc R 1 1 . .
H H142 0.3394 1.0310 0.5747 0.095 Uiso calc R 1 1 . .
H H143 0.3087 0.8916 0.5164 0.095 Uiso calc R 1 1 . .
C C16 0.30034(7) 0.98782(15) 0.22102(8) 0.0352(3) Uani d . 1 1 . .
C C17 0.25166(7) 1.01571(16) 0.14306(8) 0.0400(4) Uani d . 1 1 . .
H H17 0.2498 1.1113 0.1217 0.048 Uiso calc R 1 1 . .
C C18 0.20430(7) 0.91006(18) 0.09300(8) 0.0445(4) Uani d . 1 1 . .
C C19 0.16057(9) 0.9464(2) 0.00524(9) 0.0620(5) Uani d . 1 1 . .
H H191 0.1762 0.8945 -0.0262 0.093 Uiso calc R 1 1 . .
H H192 0.1614 1.0532 -0.0026 0.093 Uiso calc R 1 1 . .
H H193 0.1158 0.9152 -0.0125 0.093 Uiso calc R 1 1 . .
C C20 0.35276(8) 1.09906(17) 0.26778(9) 0.0468(4) Uani d . 1 1 . .
H H201 0.3460 1.1426 0.3093 0.070 Uiso calc R 1 1 . .
H H202 0.3511 1.1769 0.2316 0.070 Uiso calc R 1 1 . .
H H203 0.3955 1.0505 0.2931 0.070 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 152 0.0033 0.0016
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 232 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 8 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 8 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
_geom_angle_publ_flag
C16 N15 C1 . . 126.49(12) ?
C16 N15 H15 . . 110.4(10) ?
C1 N15 H15 . . 123.0(10) ?
C6 C1 C2 . . 121.74(12) ?
C6 C1 N15 . . 117.22(12) ?
C2 C1 N15 . . 121.01(11) ?
C3 C2 C1 . . 114.89(12) ?
C3 C2 C7 . . 121.29(12) ?
C1 C2 C7 . . 123.81(11) ?
C4 C3 C2 . . 123.21(13) ?
C4 C3 H3 . . 118.4 ?
C2 C3 H3 . . 118.4 ?
C3 C4 C5 . . 121.62(13) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C4 C5 C6 . . 115.96(12) ?
C4 C5 C11 . . 123.27(12) ?
C6 C5 C11 . . 120.75(12) ?
C1 C6 C5 . . 122.57(13) ?
C1 C6 H6 . . 118.7 ?
C5 C6 H6 . . 118.7 ?
C8 C7 C10 . . 107.28(11) ?
C8 C7 C9 . . 110.23(11) ?
C10 C7 C9 . . 106.40(11) ?
C8 C7 C2 . . 110.44(11) ?
C10 C7 C2 . . 111.39(11) ?
C9 C7 C2 . . 110.96(11) ?
C7 C8 H81 . . 109.5 ?
C7 C8 H82 . . 109.5 ?
H81 C8 H82 . . 109.5 ?
C7 C8 H83 . . 109.5 ?
H81 C8 H83 . . 109.5 ?
H82 C8 H83 . . 109.5 ?
C7 C9 H91 . . 109.5 ?
C7 C9 H92 . . 109.5 ?
H91 C9 H92 . . 109.5 ?
C7 C9 H93 . . 109.5 ?
H91 C9 H93 . . 109.5 ?
H92 C9 H93 . . 109.5 ?
C7 C10 H101 . . 109.5 ?
C7 C10 H102 . . 109.5 ?
H101 C10 H102 . . 109.5 ?
C7 C10 H103 . . 109.5 ?
H101 C10 H103 . . 109.5 ?
H102 C10 H103 . . 109.5 ?
C14 C11 C12 . . 109.23(14) ?
C14 C11 C5 . . 110.88(12) ?
C12 C11 C5 . . 111.88(13) ?
C14 C11 C13 . . 108.59(15) ?
C12 C11 C13 . . 108.44(14) ?
C5 C11 C13 . . 107.73(12) ?
C11 C12 H121 . . 109.5 ?
C11 C12 H122 . . 109.5 ?
H121 C12 H122 . . 109.5 ?
C11 C12 H123 . . 109.5 ?
H121 C12 H123 . . 109.5 ?
H122 C12 H123 . . 109.5 ?
C11 C13 H131 . . 109.5 ?
C11 C13 H132 . . 109.5 ?
H131 C13 H132 . . 109.5 ?
C11 C13 H133 . . 109.5 ?
H131 C13 H133 . . 109.5 ?
H132 C13 H133 . . 109.5 ?
C11 C14 H141 . . 109.5 ?
C11 C14 H142 . . 109.5 ?
H141 C14 H142 . . 109.5 ?
C11 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
N15 C16 C17 . . 120.22(13) ?
N15 C16 C20 . . 118.68(12) ?
C17 C16 C20 . . 121.02(13) ?
C16 C17 C18 . . 123.81(14) ?
C16 C17 H17 . . 118.1 ?
C18 C17 H17 . . 118.1 ?
O18 C18 C17 . . 123.28(13) ?
O18 C18 C19 . . 118.33(15) ?
C17 C18 C19 . . 118.33(15) ?
C18 C19 H191 . . 109.5 ?
C18 C19 H192 . . 109.5 ?
H191 C19 H192 . . 109.5 ?
C18 C19 H193 . . 109.5 ?
H191 C19 H193 . . 109.5 ?
H192 C19 H193 . . 109.5 ?
C16 C20 H201 . . 109.5 ?
C16 C20 H202 . . 109.5 ?
H201 C20 H202 . . 109.5 ?
C16 C20 H203 . . 109.5 ?
H201 C20 H203 . . 109.5 ?
H202 C20 H203 . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O18 C18 . 1.2541(19) yes
N15 C16 . 1.3447(18) yes
N15 C1 . 1.4280(16) yes
N15 H15 . 0.908(17) ?
C1 C6 . 1.3888(18) ?
C1 C2 . 1.4066(18) ?
C2 C3 . 1.3935(18) ?
C2 C7 . 1.5411(17) ?
C3 C4 . 1.387(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.388(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3911(18) ?
C5 C11 . 1.5324(19) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.5354(19) ?
C7 C10 . 1.5365(18) ?
C7 C9 . 1.5374(19) ?
C8 H81 . 0.9800 ?
C8 H82 . 0.9800 ?
C8 H83 . 0.9800 ?
C9 H91 . 0.9800 ?
C9 H92 . 0.9800 ?
C9 H93 . 0.9800 ?
C10 H101 . 0.9800 ?
C10 H102 . 0.9800 ?
C10 H103 . 0.9800 ?
C11 C14 . 1.525(2) ?
C11 C12 . 1.528(2) ?
C11 C13 . 1.533(2) ?
C12 H121 . 0.9800 ?
C12 H122 . 0.9800 ?
C12 H123 . 0.9800 ?
C13 H131 . 0.9800 ?
C13 H132 . 0.9800 ?
C13 H133 . 0.9800 ?
C14 H141 . 0.9800 ?
C14 H142 . 0.9800 ?
C14 H143 . 0.9800 ?
C16 C17 . 1.3797(19) yes
C16 C20 . 1.496(2) ?
C17 C18 . 1.418(2) yes
C17 H17 . 0.9500 ?
C18 C19 . 1.510(2) ?
C19 H191 . 0.9800 ?
C19 H192 . 0.9800 ?
C19 H193 . 0.9800 ?
C20 H201 . 0.9800 ?
C20 H202 . 0.9800 ?
C20 H203 . 0.9800 ?
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
_geom_hbond_publ_flag
N15 H15 O18 . 0.908(17) 1.848(17) 2.6376(15) 144.1(15) yes
C20 H201 O18 4_555 0.98 2.52 3.474(2) 164 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 N15 C1 C6 . . . . 65.87(17) ?
C16 N15 C1 C2 . . . . -116.26(15) ?
C6 C1 C2 C3 . . . . -0.26(19) ?
N15 C1 C2 C3 . . . . -178.03(12) ?
C6 C1 C2 C7 . . . . -179.02(12) ?
N15 C1 C2 C7 . . . . 3.21(19) ?
C1 C2 C3 C4 . . . . -0.5(2) ?
C7 C2 C3 C4 . . . . 178.27(13) ?
C2 C3 C4 C5 . . . . 0.8(2) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C3 C4 C5 C11 . . . . -178.53(14) ?
C2 C1 C6 C5 . . . . 0.8(2) ?
N15 C1 C6 C5 . . . . 178.71(12) ?
C4 C5 C6 C1 . . . . -0.6(2) ?
C11 C5 C6 C1 . . . . 177.79(13) ?
C3 C2 C7 C8 . . . . -121.41(14) ?
C1 C2 C7 C8 . . . . 57.28(16) ?
C3 C2 C7 C10 . . . . -2.30(18) ?
C1 C2 C7 C10 . . . . 176.39(12) ?
C3 C2 C7 C9 . . . . 116.04(14) ?
C1 C2 C7 C9 . . . . -65.27(16) ?
C4 C5 C11 C14 . . . . -143.77(16) ?
C6 C5 C11 C14 . . . . 37.95(19) ?
C4 C5 C11 C12 . . . . -21.6(2) ?
C6 C5 C11 C12 . . . . 160.16(14) ?
C4 C5 C11 C13 . . . . 97.53(17) ?
C6 C5 C11 C13 . . . . -80.74(17) ?
C1 N15 C16 C17 . . . . 176.87(12) ?
C1 N15 C16 C20 . . . . 0.26(19) ?
N15 C16 C17 C18 . . . . -2.8(2) ?
C20 C16 C17 C18 . . . . 173.76(13) ?
C16 C17 C18 O18 . . . . 6.9(2) ?
C16 C17 C18 C19 . . . . -170.40(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656718
