#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224808.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_2224808
loop_
_publ_author_name
'Wang, Lei'
'Ma, Li-Ying'
'Huang, Yu-Ling'
'Zheng, Bai-Yu'
_publ_section_title
;
 (E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one
;
_journal_coeditor_code           XU2690
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o174
_journal_paper_doi               10.1107/S1600536809052398
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N O'
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_name_systematic
;
(E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   7.276(2)
_cell_length_b                   11.567(3)
_cell_length_c                   17.642(5)
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0267
_cell_volume                     1484.8(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 1999)'
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000)'
_computing_molecular_graphics    'PLEASE PROVIDE'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16704
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.308
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0610
_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)+(0.0495P)²+0.3222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                1846
_reflns_number_total             1958
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2690.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'p 2ac 2ab'
_cod_database_code               2224808
_cod_database_fobs_code          2224808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_disorder_assembly
_atom_site_disorder_group
O O1 0.9451(4) 0.62914(17) 0.28002(11) 0.0570(7) Uani d . 1 . .
N N1 1.0052(4) 0.9449(2) -0.14961(12) 0.0474(7) Uani d . 1 . .
C C1 0.9388(4) 0.8121(2) 0.07087(15) 0.0340(6) Uani d . 1 . .
C C2 1.0071(4) 0.9237(2) 0.05857(14) 0.0342(6) Uani d . 1 . .
H H2 1.0393 0.9701 0.1010 0.041 Uiso calc R 1 . .
C C3 1.0288(4) 0.9681(2) -0.01345(15) 0.0355(6) Uani d . 1 . .
H H3 1.0754 1.0442 -0.0195 0.043 Uiso calc R 1 . .
C C4 0.9833(4) 0.9029(2) -0.07801(15) 0.0361(6) Uani d . 1 . .
C C5 0.9100(4) 0.7916(2) -0.06585(15) 0.0389(6) Uani d . 1 . .
H H5 0.8734 0.7458 -0.1079 0.047 Uiso calc R 1 . .
C C6 0.8909(4) 0.7489(3) 0.00638(17) 0.0377(6) Uani d . 1 . .
H H6 0.8431 0.6732 0.0127 0.045 Uiso calc R 1 . .
C C7 0.9790(4) 0.7943(2) 0.35669(14) 0.0339(6) Uani d . 1 . .
C C8 1.0590(4) 0.7345(2) 0.41698(16) 0.0395(6) Uani d . 1 . .
H H8 1.1025 0.6580 0.4094 0.047 Uiso calc R 1 . .
C C9 1.0757(4) 0.7849(2) 0.48706(16) 0.0424(7) Uani d . 1 . .
H H9 1.1343 0.7435 0.5268 0.051 Uiso calc R 1 . .
C C10 1.0082(4) 0.8956(3) 0.50109(15) 0.0399(6) Uani d . 1 . .
C C11 0.9305(4) 0.9556(3) 0.44122(15) 0.0410(7) Uani d . 1 . .
H H11 0.8854 1.0317 0.4493 0.049 Uiso calc R 1 . .
C C12 0.9174(4) 0.9066(2) 0.36960(15) 0.0371(6) Uani d . 1 . .
H H12 0.8659 0.9499 0.3291 0.045 Uiso calc R 1 . .
C C13 0.9252(4) 0.7595(2) 0.14493(15) 0.0370(6) Uani d . 1 . .
H H13 0.8853 0.6813 0.1455 0.044 Uiso calc R 1 . .
C C14 0.9611(4) 0.8060(2) 0.21291(14) 0.0377(6) Uani d . 1 . .
H H14 0.9896 0.8860 0.2163 0.045 Uiso calc R 1 . .
C C15 0.9573(4) 0.7358(2) 0.28210(15) 0.0382(6) Uani d . 1 . .
C C16 1.0849(5) 1.0576(3) -0.16376(19) 0.0606(9) Uani d . 1 . .
H H16A 1.2040 1.0631 -0.1381 0.091 Uiso calc R 1 . .
H H16B 1.0025 1.1177 -0.1444 0.091 Uiso calc R 1 . .
H H16C 1.1022 1.0681 -0.2184 0.091 Uiso calc R 1 . .
C C17 0.9558(6) 0.8769(3) -0.21540(16) 0.0685(11) Uani d . 1 . .
H H17A 0.8250 0.8568 -0.2129 0.103 Uiso calc R 1 . .
H H17B 1.0294 0.8059 -0.2164 0.103 Uiso calc R 1 . .
H H17C 0.9794 0.9218 -0.2615 0.103 Uiso calc R 1 . .
C C18 1.0179(5) 0.9481(3) 0.57936(17) 0.0571(9) Uani d . 1 . .
H H18A 0.9012 0.9352 0.6058 0.086 Uiso d R 1 . .
H H18B 1.0408 1.0314 0.5751 0.086 Uiso d R 1 . .
H H18C 1.1179 0.9119 0.6080 0.086 Uiso d R 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C17 . . 121.4(3) ?
C4 N1 C16 . . 121.8(2) ?
C17 N1 C16 . . 116.8(2) ?
C6 C1 C2 . . 116.4(2) ?
C6 C1 C13 . . 120.0(2) ?
C2 C1 C13 . . 123.6(2) ?
C3 C2 C1 . . 121.8(2) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
C2 C3 C4 . . 121.3(2) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
N1 C4 C3 . . 122.2(2) ?
N1 C4 C5 . . 120.7(2) ?
C3 C4 C5 . . 117.1(2) ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 122.9(3) ?
C5 C6 H6 . . 118.6 ?
C1 C6 H6 . . 118.6 ?
C12 C7 C8 . . 118.1(2) ?
C12 C7 C15 . . 122.3(2) ?
C8 C7 C15 . . 119.5(2) ?
C9 C8 C7 . . 120.9(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 121.3(3) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C11 C10 C9 . . 118.0(3) ?
C11 C10 C18 . . 121.0(3) ?
C9 C10 C18 . . 121.1(3) ?
C10 C11 C12 . . 121.1(3) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
C11 C12 C7 . . 120.5(3) ?
C11 C12 H12 . . 119.7 ?
C7 C12 H12 . . 119.7 ?
C14 C13 C1 . . 128.8(2) ?
C14 C13 H13 . . 115.6 ?
C1 C13 H13 . . 115.6 ?
C13 C14 C15 . . 121.3(2) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
O1 C15 C14 . . 121.9(2) ?
O1 C15 C7 . . 119.1(2) ?
C14 C15 C7 . . 118.9(2) ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C10 C18 H18A . . 109.5 ?
C10 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C10 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
O1 C15 . 1.238(3) ?
N1 C4 . 1.363(3) ?
N1 C17 . 1.448(4) ?
N1 C16 . 1.448(4) ?
C1 C6 . 1.396(4) ?
C1 C2 . 1.400(4) ?
C1 C13 . 1.445(4) ?
C2 C3 . 1.380(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.405(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.410(4) ?
C5 C6 . 1.374(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C12 . 1.393(4) ?
C7 C8 . 1.396(4) ?
C7 C15 . 1.488(4) ?
C8 C9 . 1.372(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.393(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.385(4) ?
C10 C18 . 1.510(4) ?
C11 C12 . 1.388(4) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.340(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.466(4) ?
C14 H14 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 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
C11 H11 Cg1 4_674 0.95 2.94 3.697(3) 138 y
C9 H9 Cg2 2_466 0.95 2.93 3.712(3) 141 y
C16 H16B Cg2 4_775 0.98 2.70 3.643(3) 161 y
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
C6 C1 C2 C3 . . . . -1.1(4) ?
C13 C1 C2 C3 . . . . 175.8(3) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C17 N1 C4 C3 . . . . -179.3(3) ?
C16 N1 C4 C3 . . . . 3.0(4) ?
C17 N1 C4 C5 . . . . -0.5(4) ?
C16 N1 C4 C5 . . . . -178.3(3) ?
C2 C3 C4 N1 . . . . -179.5(3) ?
C2 C3 C4 C5 . . . . 1.7(4) ?
N1 C4 C5 C6 . . . . 179.0(3) ?
C3 C4 C5 C6 . . . . -2.2(4) ?
C4 C5 C6 C1 . . . . 1.1(4) ?
C2 C1 C6 C5 . . . . 0.6(4) ?
C13 C1 C6 C5 . . . . -176.4(3) ?
C12 C7 C8 C9 . . . . 0.3(4) ?
C15 C7 C8 C9 . . . . -178.0(3) ?
C7 C8 C9 C10 . . . . 2.1(4) ?
C8 C9 C10 C11 . . . . -2.7(4) ?
C8 C9 C10 C18 . . . . 176.7(3) ?
C9 C10 C11 C12 . . . . 1.0(4) ?
C18 C10 C11 C12 . . . . -178.4(3) ?
C10 C11 C12 C7 . . . . 1.4(4) ?
C8 C7 C12 C11 . . . . -2.0(4) ?
C15 C7 C12 C11 . . . . 176.2(3) ?
C6 C1 C13 C14 . . . . -178.7(3) ?
C2 C1 C13 C14 . . . . 4.6(5) ?
C1 C13 C14 C15 . . . . -173.8(3) ?
C13 C14 C15 O1 . . . . 9.7(5) ?
C13 C14 C15 C7 . . . . -173.7(3) ?
C12 C7 C15 O1 . . . . -151.9(3) ?
C8 C7 C15 O1 . . . . 26.3(4) ?
C12 C7 C15 C14 . . . . 31.4(4) ?
C8 C7 C15 C14 . . . . -150.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4770831
