#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218351.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_2218351
loop_
_publ_author_name
'Zhang, Li-Ping'
'Ni, Cai-Hua'
'Li, Zhi-Yong'
'Zhang, Wei'
_publ_section_title
;
 (Z)-Methyl 3-(4-ethoxyanilino)but-2-enoate
;
_journal_coeditor_code           CI2569
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1051
_journal_paper_doi               10.1107/S160053680800891X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H17 N O3'
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_chemical_name_systematic
;
(Z)-Methyl 3-(4-ethoxyanilino)but-2-enoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.519(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.421(2)
_cell_length_b                   6.3372(13)
_cell_length_c                   16.569(3)
_cell_measurement_reflns_used    2289
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.47
_cell_volume                     1295.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6917
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.990000
_exptl_absorpt_correction_T_min  0.942003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.106
_refine_ls_extinction_coef       0.106(7)
_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   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+0.1223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                1629
_reflns_number_total             2628
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2569.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        1295.7(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218351
_cod_database_fobs_code          2218351
loop_
_symmetry_equiv_pos_as_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_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
O O1 0.11751(9) 1.2475(2) 1.03170(8) 0.0714(4) Uani d . 1
O O2 0.55147(10) 0.4131(2) 0.90568(7) 0.0697(4) Uani d . 1
O O3 0.60606(12) 0.2866(2) 0.79053(8) 0.0872(5) Uani d . 1
N N1 0.39962(11) 0.7279(2) 0.88382(9) 0.0654(4) Uani d . 1
H H1 0.4403 0.6528 0.9181 0.078 Uiso calc R 1
C C1 0.32646(13) 0.8715(3) 0.91658(9) 0.0578(4) Uani d . 1
C C2 0.21953(14) 0.8158(3) 0.92064(10) 0.0660(5) Uani d . 1
H H2 0.1934 0.6891 0.8979 0.079 Uiso calc R 1
C C3 0.15124(13) 0.9455(3) 0.95793(11) 0.0642(5) Uani d . 1
H H3 0.0794 0.9067 0.9600 0.077 Uiso calc R 1
C C4 0.18978(13) 1.1339(3) 0.99243(10) 0.0562(4) Uani d . 1
C C5 0.29584(13) 1.1948(3) 0.98654(11) 0.0621(5) Uani d . 1
H H5 0.3216 1.3232 1.0079 0.074 Uiso calc R 1
C C6 0.36297(13) 1.0624(3) 0.94847(10) 0.0622(5) Uani d . 1
H H6 0.4341 1.1032 0.9444 0.075 Uiso calc R 1
C C7 0.15753(16) 1.4153(3) 1.08352(12) 0.0747(6) Uani d . 1
H H7A 0.1915 1.5212 1.0526 0.090 Uiso calc R 1
H H7B 0.2113 1.3624 1.1257 0.090 Uiso calc R 1
C C8 0.06476(18) 1.5100(4) 1.12071(12) 0.0860(6) Uani d . 1
H H8A 0.0129 1.5654 1.0787 0.129 Uiso calc R 1
H H8B 0.0908 1.6218 1.1569 0.129 Uiso calc R 1
H H8C 0.0309 1.4036 1.1505 0.129 Uiso calc R 1
C C9 0.41069(14) 0.6995(3) 0.80498(10) 0.0606(5) Uani d . 1
C C10 0.34385(18) 0.8388(4) 0.74539(12) 0.0856(6) Uani d . 1
H H10A 0.2687 0.8250 0.7530 0.128 Uiso calc R 1
H H10B 0.3542 0.7976 0.6911 0.128 Uiso calc R 1
H H10C 0.3660 0.9830 0.7541 0.128 Uiso calc R 1
C C11 0.48003(16) 0.5549(3) 0.77912(11) 0.0682(5) Uani d . 1
H H11 0.4847 0.5450 0.7236 0.082 Uiso calc R 1
C C12 0.54568(14) 0.4182(3) 0.83178(11) 0.0603(5) Uani d . 1
C C13 0.66598(19) 0.1247(4) 0.83608(13) 0.0913(7) Uani d . 1
H H13A 0.7034 0.1842 0.8847 0.137 Uiso calc R 1
H H13B 0.7176 0.0641 0.8038 0.137 Uiso calc R 1
H H13C 0.6171 0.0170 0.8503 0.137 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0558(7) 0.0803(9) 0.0782(8) 0.0017(6) 0.0075(6) -0.0156(7)
O2 0.0708(8) 0.0769(9) 0.0602(8) 0.0030(6) 0.0030(6) -0.0031(6)
O3 0.1112(11) 0.0823(10) 0.0680(8) 0.0315(8) 0.0100(7) -0.0054(7)
N1 0.0600(9) 0.0757(10) 0.0604(9) 0.0114(7) 0.0069(7) 0.0021(7)
C1 0.0526(10) 0.0670(11) 0.0537(9) -0.0002(8) 0.0050(7) 0.0037(8)
C2 0.0572(11) 0.0703(12) 0.0701(11) -0.0124(9) 0.0062(8) -0.0107(9)
C3 0.0465(9) 0.0752(13) 0.0709(11) -0.0097(8) 0.0067(8) -0.0097(9)
C4 0.0497(9) 0.0632(10) 0.0546(9) 0.0017(8) 0.0015(7) 0.0024(8)
C5 0.0540(10) 0.0603(11) 0.0710(11) -0.0080(8) 0.0030(8) -0.0018(9)
C6 0.0481(10) 0.0686(12) 0.0698(11) -0.0075(8) 0.0063(8) 0.0057(9)
C7 0.0787(13) 0.0724(13) 0.0724(12) 0.0010(10) 0.0071(9) -0.0102(10)
C8 0.0949(15) 0.0886(15) 0.0745(12) 0.0188(12) 0.0097(11) -0.0090(11)
C9 0.0589(10) 0.0621(11) 0.0613(10) -0.0050(8) 0.0087(8) 0.0037(8)
C10 0.0966(15) 0.0921(15) 0.0697(12) 0.0227(12) 0.0170(11) 0.0152(11)
C11 0.0787(13) 0.0715(12) 0.0552(10) 0.0040(10) 0.0118(9) 0.0015(9)
C12 0.0607(11) 0.0566(10) 0.0642(11) -0.0066(8) 0.0088(8) -0.0060(9)
C13 0.1021(16) 0.0811(15) 0.0877(15) 0.0275(12) -0.0022(12) -0.0071(12)
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
C4 O1 C7 118.48(14)
C12 O3 C13 117.32(15)
C9 N1 C1 126.37(15)
C9 N1 H1 116.8
C1 N1 H1 116.8
C6 C1 C2 118.81(16)
C6 C1 N1 120.47(15)
C2 C1 N1 120.63(16)
C3 C2 C1 120.90(17)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 119.86(16)
C2 C3 H3 120.1
C4 C3 H3 120.1
O1 C4 C3 115.74(15)
O1 C4 C5 124.43(16)
C3 C4 C5 119.83(16)
C6 C5 C4 119.30(17)
C6 C5 H5 120.4
C4 C5 H5 120.4
C1 C6 C5 121.23(16)
C1 C6 H6 119.4
C5 C6 H6 119.4
O1 C7 C8 108.47(16)
O1 C7 H7A 110.0
C8 C7 H7A 110.0
O1 C7 H7B 110.0
C8 C7 H7B 110.0
H7A C7 H7B 108.4
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 C11 122.43(16)
N1 C9 C10 116.80(16)
C11 C9 C10 120.76(16)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 C12 123.90(16)
C9 C11 H11 118.0
C12 C11 H11 118.0
O2 C12 O3 121.13(16)
O2 C12 C11 126.71(16)
O3 C12 C11 112.16(16)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 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
O1 C4 1.371(2)
O1 C7 1.420(2)
O2 C12 1.2187(19)
O3 C12 1.357(2)
O3 C13 1.431(2)
N1 C9 1.341(2)
N1 C1 1.435(2)
N1 H1 0.86
C1 C6 1.376(2)
C1 C2 1.383(2)
C2 C3 1.377(3)
C2 H2 0.93
C3 C4 1.385(2)
C3 H3 0.93
C4 C5 1.387(2)
C5 C6 1.384(2)
C5 H5 0.93
C6 H6 0.93
C7 C8 1.493(3)
C7 H7A 0.97
C7 H7B 0.97
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
C9 C11 1.360(3)
C9 C10 1.503(3)
C10 H10A 0.96
C10 H10B 0.96
C10 H10C 0.96
C11 C12 1.420(3)
C11 H11 0.93
C13 H13A 0.96
C13 H13B 0.96
C13 H13C 0.96
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 H1 O2 . 0.86 2.08 2.741(2) 133
C6 H6 O2 1_565 0.93 2.57 3.362(3) 143
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
C9 N1 C1 C6 -100.4(2)
C9 N1 C1 C2 83.0(2)
C6 C1 C2 C3 -1.9(3)
N1 C1 C2 C3 174.69(16)
C1 C2 C3 C4 -0.4(3)
C7 O1 C4 C3 165.99(15)
C7 O1 C4 C5 -13.3(2)
C2 C3 C4 O1 -176.87(16)
C2 C3 C4 C5 2.5(3)
O1 C4 C5 C6 177.09(16)
C3 C4 C5 C6 -2.2(2)
C2 C1 C6 C5 2.2(3)
N1 C1 C6 C5 -174.42(15)
C4 C5 C6 C1 -0.1(3)
C4 O1 C7 C8 -178.42(16)
C1 N1 C9 C11 -177.96(17)
C1 N1 C9 C10 3.2(3)
N1 C9 C11 C12 1.1(3)
C10 C9 C11 C12 179.97(18)
C13 O3 C12 O2 7.7(3)
C13 O3 C12 C11 -172.85(18)
C9 C11 C12 O2 -1.7(3)
C9 C11 C12 O3 178.90(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28595998
