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#$Date: 2023-03-09 12:29:03 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281773 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106900.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.
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data_8106900
loop_
_publ_author_name
'Ghorab, Mostafa M.'
'Alsaid, Mansour S.'
'Ghabbour, Hazem A.'
'Fun, Hoong-Kun'
_publ_section_title
;
 Crystal structure of
 (E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C13H17NO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              437
_journal_page_last               438
_journal_paper_doi               10.1515/ncrs-2015-0121
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 100.341(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7486(4)
_cell_length_b                   8.5148(3)
_cell_length_c                   19.9822(9)
_cell_measurement_reflns_used    8509
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.24
_cell_measurement_theta_min      2.61
_cell_volume                     1296.97(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18633
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.607
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.451
_exptl_crystal_size_min          0.368
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0807P)²+0.4387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2001
_reflns_number_total             2952
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0121_suppl.cif
_cod_data_source_block           a_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106900
_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_min   0.952
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.8252(2) 0.25465(19) 0.90088(7) 0.0712(5) Uani 1 1 d . . . . .
O2 O 0.8774(2) 0.51700(17) 0.84231(7) 0.0627(4) Uani 1 1 d . . . . .
O3 O 0.6798(4) 0.4273(3) 0.59200(8) 0.1177(10) Uani 1 1 d . . . . .
N1 N 0.3138(2) 0.1676(2) 0.46542(8) 0.0608(5) Uani 1 1 d . . . . .
C1 C 0.6169(3) 0.1607(2) 0.72517(10) 0.0526(5) Uani 1 1 d . . . . .
H1A H 0.5533 0.0784 0.6997 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6753(3) 0.1417(2) 0.79443(10) 0.0547(5) Uani 1 1 d . . . . .
H2A H 0.6537 0.0458 0.8158 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7645(3) 0.2610(2) 0.83254(9) 0.0502(5) Uani 1 1 d . . . . .
C4 C 0.7947(2) 0.4030(2) 0.80069(9) 0.0451(4) Uani 1 1 d . . . . .
C5 C 0.7409(2) 0.4181(2) 0.73148(9) 0.0461(5) Uani 1 1 d . . . . .
H5A H 0.7660 0.5123 0.7096 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6499(2) 0.2976(2) 0.69275(9) 0.0464(5) Uani 1 1 d . . . . .
C7 C 0.6009(3) 0.3230(3) 0.61739(10) 0.0617(6) Uani 1 1 d . . . . .
C8 C 0.4683(3) 0.2278(3) 0.57865(10) 0.0557(5) Uani 1 1 d . . . . .
H8A H 0.4080 0.1519 0.6006 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4286(3) 0.2466(3) 0.50988(10) 0.0610(6) Uani 1 1 d . . . . .
H9A H 0.4915 0.3267 0.4915 0.073 Uiso 1 1 calc R U . . .
C10 C 0.2075(4) 0.0465(4) 0.48702(13) 0.0841(8) Uani 1 1 d . . . . .
H10A H 0.1492 0.0871 0.5231 0.126 Uiso 1 1 calc R U . . .
H10B H 0.2818 -0.0431 0.5044 0.126 Uiso 1 1 calc R U . . .
H10C H 0.1189 0.0126 0.4484 0.126 Uiso 1 1 calc R U . . .
C11 C 0.2926(4) 0.1966(3) 0.39296(11) 0.0777(7) Uani 1 1 d . . . . .
H11A H 0.3736 0.2797 0.3845 0.117 Uiso 1 1 calc R U . . .
H11B H 0.1717 0.2295 0.3755 0.117 Uiso 1 1 calc R U . . .
H11C H 0.3182 0.1002 0.3698 0.117 Uiso 1 1 calc R U . . .
C12 C 0.8334(5) 0.1057(3) 0.93328(13) 0.0925(9) Uani 1 1 d . . . . .
H12A H 0.8755 0.1188 0.9822 0.139 Uiso 1 1 calc R U . . .
H12B H 0.9140 0.0373 0.9142 0.139 Uiso 1 1 calc R U . . .
H12C H 0.7162 0.0584 0.9258 0.139 Uiso 1 1 calc R U . . .
C13 C 0.9118(3) 0.6620(3) 0.81222(12) 0.0700(7) Uani 1 1 d . . . . .
H13A H 0.9710 0.7333 0.8475 0.105 Uiso 1 1 calc R U . . .
H13B H 0.8010 0.7091 0.7899 0.105 Uiso 1 1 calc R U . . .
H13C H 0.9872 0.6437 0.7785 0.105 Uiso 1 1 calc R U . . .
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
C3 O1 C12 118.11(18) . .
C4 O2 C13 117.72(15) . .
C9 N1 C10 121.14(19) . .
C9 N1 C11 121.8(2) . .
C10 N1 C11 117.08(19) . .
C6 C1 C2 120.80(18) . .
C6 C1 H1A 119.6 . .
C2 C1 H1A 119.6 . .
C3 C2 C1 120.48(18) . .
C3 C2 H2A 119.8 . .
C1 C2 H2A 119.8 . .
O1 C3 C2 124.95(18) . .
O1 C3 C4 115.60(17) . .
C2 C3 C4 119.43(17) . .
O2 C4 C5 124.84(17) . .
O2 C4 C3 115.80(16) . .
C5 C4 C3 119.36(17) . .
C4 C5 C6 121.30(17) . .
C4 C5 H5A 119.3 . .
C6 C5 H5A 119.3 . .
C1 C6 C5 118.56(17) . .
C1 C6 C7 123.88(17) . .
C5 C6 C7 117.51(17) . .
O3 C7 C8 123.16(19) . .
O3 C7 C6 117.38(19) . .
C8 C7 C6 119.45(19) . .
C9 C8 C7 119.5(2) . .
C9 C8 H8A 120.3 . .
C7 C8 H8A 120.3 . .
N1 C9 C8 128.4(2) . .
N1 C9 H9A 115.8 . .
C8 C9 H9A 115.8 . .
N1 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 H11A 109.5 . .
N1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 C12 H12A 109.5 . .
O1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C13 H13A 109.5 . .
O2 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O2 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.363(2) .
O1 C12 1.420(3) .
O2 C4 1.361(2) .
O2 C13 1.419(3) .
O3 C7 1.237(3) .
N1 C9 1.323(3) .
N1 C10 1.434(3) .
N1 C11 1.449(3) .
C1 C6 1.380(3) .
C1 C2 1.386(3) .
C1 H1A 0.9500 .
C2 C3 1.379(3) .
C2 H2A 0.9500 .
C3 C4 1.405(3) .
C4 C5 1.377(2) .
C5 C6 1.397(3) .
C5 H5A 0.9500 .
C6 C7 1.501(3) .
C7 C8 1.423(3) .
C8 C9 1.363(3) .
C8 H8A 0.9500 .
C9 H9A 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 1.4(3) . . . .
C12 O1 C3 C2 14.7(3) . . . .
C12 O1 C3 C4 -166.6(2) . . . .
C1 C2 C3 O1 179.1(2) . . . .
C1 C2 C3 C4 0.5(3) . . . .
C13 O2 C4 C5 -0.5(3) . . . .
C13 O2 C4 C3 179.53(19) . . . .
O1 C3 C4 O2 -1.3(3) . . . .
C2 C3 C4 O2 177.44(18) . . . .
O1 C3 C4 C5 178.65(18) . . . .
C2 C3 C4 C5 -2.6(3) . . . .
O2 C4 C5 C6 -177.17(18) . . . .
C3 C4 C5 C6 2.8(3) . . . .
C2 C1 C6 C5 -1.2(3) . . . .
C2 C1 C6 C7 176.0(2) . . . .
C4 C5 C6 C1 -1.0(3) . . . .
C4 C5 C6 C7 -178.34(18) . . . .
C1 C6 C7 O3 -159.3(2) . . . .
C5 C6 C7 O3 17.9(3) . . . .
C1 C6 C7 C8 20.6(3) . . . .
C5 C6 C7 C8 -162.17(19) . . . .
O3 C7 C8 C9 2.5(4) . . . .
C6 C7 C8 C9 -177.4(2) . . . .
C10 N1 C9 C8 1.6(4) . . . .
C11 N1 C9 C8 -176.9(2) . . . .
C7 C8 C9 N1 178.2(2) . . . .
