#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225004.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_2225004
loop_
_publ_author_name
'Li, Xiang'
_publ_section_title
;
 (E)-N-(3,4-Dimethoxyphenethyl)-3-methoxybut-2-enamide
;
_journal_coeditor_code           HG2630
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o432
_journal_paper_doi               10.1107/S1600536810001972
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H21 N O4'
_chemical_formula_moiety         'C15 H21 N O4'
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33
_chemical_name_systematic
;
(E)-N-(3,4-Dimethoxyphenethyl)-3-methoxybut-2-enamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.509(3)
_cell_length_b                   14.930(3)
_cell_length_c                   8.2998(17)
_cell_measurement_reflns_used    4588
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4844
_cell_measurement_theta_min      1.3639
_cell_volume                     1477.6(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury CCD/AFC'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10754
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0586
_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)+(0.0450P)²+0.6856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                2435
_reflns_number_total             2591
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2630.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1477.5(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225004
_cod_database_fobs_code          2225004
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
O O1 1.17428(12) 0.48028(10) 0.66017(19) 0.0356(4) Uani d . 1 . .
O O2 1.16017(13) 0.30958(10) 0.6857(2) 0.0446(4) Uani d . 1 . .
O O3 0.57963(13) 0.16546(10) 0.56367(18) 0.0352(4) Uani d . 1 . .
O O4 0.36035(13) 0.06101(10) 0.8340(2) 0.0417(4) Uani d . 1 . .
N N1 0.62813(14) 0.26957(12) 0.7715(2) 0.0308(4) Uani d . 1 . .
H H1A 0.6128 0.2920 0.8601 0.037 Uiso calc R 1 . .
C C1 0.91080(17) 0.37551(15) 0.8108(3) 0.0303(5) Uani d . 1 . .
C C2 0.99168(17) 0.32078(14) 0.7740(3) 0.0320(5) Uani d . 1 . .
H H2A 0.9871 0.2576 0.7838 0.038 Uiso calc R 1 . .
C C3 1.07767(17) 0.35758(14) 0.7239(3) 0.0307(5) Uani d . 1 . .
C C4 1.08529(16) 0.45083(14) 0.7088(2) 0.0285(5) Uani d . 1 . .
C C5 1.00533(18) 0.50451(14) 0.7431(3) 0.0321(5) Uani d . 1 . .
H H5A 1.0093 0.5677 0.7322 0.038 Uiso calc R 1 . .
C C6 0.91870(18) 0.46703(15) 0.7936(3) 0.0331(5) Uani d . 1 . .
H H6A 0.8642 0.5050 0.8167 0.040 Uiso calc R 1 . .
C C7 1.1604(2) 0.21485(16) 0.7102(3) 0.0484(6) Uani d . 1 . .
H H7A 1.2231 0.1881 0.6793 0.073 Uiso calc R 1 . .
H H7B 1.0896 0.1895 0.6390 0.073 Uiso calc R 1 . .
H H7C 1.1688 0.2019 0.8292 0.073 Uiso calc R 1 . .
C C8 1.1861(2) 0.57474(15) 0.6482(3) 0.0379(5) Uani d . 1 . .
H H8A 1.2524 0.5878 0.6126 0.057 Uiso calc R 1 . .
H H8B 1.1948 0.6022 0.7587 0.057 Uiso calc R 1 . .
H H8C 1.1192 0.5992 0.5650 0.057 Uiso calc R 1 . .
C C9 0.81715(17) 0.33412(16) 0.8642(3) 0.0342(5) Uani d . 1 . .
H H9A 0.7954 0.3757 0.9418 0.041 Uiso calc R 1 . .
H H9B 0.8445 0.2781 0.9271 0.041 Uiso calc R 1 . .
C C10 0.71449(17) 0.31312(15) 0.7155(3) 0.0316(5) Uani d . 1 . .
H H10A 0.6843 0.3693 0.6557 0.038 Uiso calc R 1 . .
H H10B 0.7364 0.2735 0.6351 0.038 Uiso calc R 1 . .
C C11 0.57000(16) 0.19712(14) 0.6969(3) 0.0283(5) Uani d . 1 . .
C C12 0.49832(17) 0.15920(14) 0.7913(3) 0.0304(5) Uani d . 1 . .
H H12A 0.5082 0.1820 0.9017 0.036 Uiso calc R 1 . .
C C13 0.42041(17) 0.09551(14) 0.7360(3) 0.0321(5) Uani d . 1 . .
C C14 0.3818(2) 0.05392(18) 0.5650(3) 0.0500(7) Uani d . 1 . .
H H14A 0.4248 0.0788 0.4944 0.075 Uiso calc R 1 . .
H H14B 0.3019 0.0667 0.5129 0.075 Uiso calc R 1 . .
H H14C 0.3933 -0.0110 0.5751 0.075 Uiso calc R 1 . .
C C15 0.3837(2) 0.09322(19) 1.0043(3) 0.0500(7) Uani d . 1 . .
H H15A 0.3349 0.0627 1.0594 0.075 Uiso calc R 1 . .
H H15B 0.3700 0.1579 1.0026 0.075 Uiso calc R 1 . .
H H15C 0.4623 0.0811 1.0669 0.075 Uiso calc 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 O1 C8 . . 116.74(16) ?
C3 O2 C7 . . 117.00(18) ?
C13 O4 C15 . . 118.37(18) ?
C11 N1 C10 . . 124.27(17) ?
C11 N1 H1A . . 117.9 ?
C10 N1 H1A . . 117.9 ?
C6 C1 C2 . . 118.36(19) ?
C6 C1 C9 . . 121.55(19) ?
C2 C1 C9 . . 120.1(2) ?
C3 C2 C1 . . 120.8(2) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
O2 C3 C2 . . 124.9(2) ?
O2 C3 C4 . . 114.96(18) ?
C2 C3 C4 . . 120.15(19) ?
O1 C4 C5 . . 125.55(19) ?
O1 C4 C3 . . 115.39(18) ?
C5 C4 C3 . . 119.06(19) ?
C4 C5 C6 . . 120.6(2) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
C1 C6 C5 . . 121.0(2) ?
C1 C6 H6A . . 119.5 ?
C5 C6 H6A . . 119.5 ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 C8 H8A . . 109.5 ?
O1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C1 C9 C10 . . 112.77(17) ?
C1 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
C1 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
N1 C10 C9 . . 111.08(17) ?
N1 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
N1 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
O3 C11 N1 . . 122.13(18) ?
O3 C11 C12 . . 124.53(19) ?
N1 C11 C12 . . 113.31(18) ?
C13 C12 C11 . . 126.0(2) ?
C13 C12 H12A . . 117.0 ?
C11 C12 H12A . . 117.0 ?
C12 C13 O4 . . 122.6(2) ?
C12 C13 C14 . . 128.0(2) ?
O4 C13 C14 . . 109.43(19) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 C4 . 1.366(2) ?
O1 C8 . 1.425(3) ?
O2 C3 . 1.370(2) ?
O2 C7 . 1.429(3) ?
O3 C11 . 1.241(2) ?
O4 C13 . 1.364(2) ?
O4 C15 . 1.436(3) ?
N1 C11 . 1.345(3) ?
N1 C10 . 1.453(2) ?
N1 H1A . 0.8800 ?
C1 C6 . 1.380(3) ?
C1 C2 . 1.404(3) ?
C1 C9 . 1.505(3) ?
C2 C3 . 1.379(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.404(3) ?
C4 C5 . 1.377(3) ?
C5 C6 . 1.392(3) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.521(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.471(3) ?
C12 C13 . 1.339(3) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.490(3) ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 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
N1 H1A O3 4_566 0.88 1.96 2.842(2) 176.4
C15 H15A O1 4_466 0.98 2.48 3.434(3) 163.8
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 . . . . 0.7(3) ?
C9 C1 C2 C3 . . . . 179.61(19) ?
C7 O2 C3 C2 . . . . -4.2(3) ?
C7 O2 C3 C4 . . . . 175.8(2) ?
C1 C2 C3 O2 . . . . 179.9(2) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C8 O1 C4 C5 . . . . 1.6(3) ?
C8 O1 C4 C3 . . . . -178.34(18) ?
O2 C3 C4 O1 . . . . -0.7(3) ?
C2 C3 C4 O1 . . . . 179.31(18) ?
O2 C3 C4 C5 . . . . 179.38(19) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
O1 C4 C5 C6 . . . . -179.30(19) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C2 C1 C6 C5 . . . . -0.7(3) ?
C9 C1 C6 C5 . . . . -179.60(19) ?
C4 C5 C6 C1 . . . . 0.1(3) ?
C6 C1 C9 C10 . . . . 89.1(3) ?
C2 C1 C9 C10 . . . . -89.8(2) ?
C11 N1 C10 C9 . . . . -134.8(2) ?
C1 C9 C10 N1 . . . . 177.36(18) ?
C10 N1 C11 O3 . . . . -5.9(3) ?
C10 N1 C11 C12 . . . . 172.39(18) ?
O3 C11 C12 C13 . . . . -11.6(3) ?
N1 C11 C12 C13 . . . . 170.1(2) ?
C11 C12 C13 O4 . . . . 177.17(19) ?
C11 C12 C13 C14 . . . . -5.3(4) ?
C15 O4 C13 C12 . . . . -1.4(3) ?
C15 O4 C13 C14 . . . . -179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744322
