#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209388.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_2209388
loop_
_publ_author_name
'Xu, Fada'
'Ma, Cheng'
'Zhang, Yi-Ping'
_publ_section_title
;
 (E)-Dimethyl 4-(ethylamino)-5-styrylfuran-2,3-dicarboxylate
;
_journal_coeditor_code           BH2028
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2886
_journal_page_last               o2887
_journal_paper_doi               10.1107/S1600536806022586
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H19 N1 O5'
_chemical_formula_moiety         'C18 H19 N1 O5'
_chemical_formula_sum            'C18 H19 N O5'
_chemical_formula_weight         329.34
_chemical_melting_point          391.5(5)
_chemical_name_systematic
;
(E)-Dimethyl 4-(ethylamino)-5-styrylfuran-2,3-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                70.17(3)
_cell_angle_beta                 82.36(3)
_cell_angle_gamma                75.52(3)
_cell_formula_units_Z            2
_cell_length_a                   7.765(4)
_cell_length_b                   9.043(4)
_cell_length_c                   13.044(11)
_cell_measurement_reflns_used    5627
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     833.1(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8262
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.273
_refine_ls_extinction_coef       0.032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0782P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.144
_reflns_number_gt                2119
_reflns_number_total             3772
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2028.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '391-392' was changed to '391.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '391-392' was changed to '391.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C18 H19 N1 O5'
_cod_database_code               2209388
_cod_database_fobs_code          2209388
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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
C C1 0.4641(2) 0.0790(2) 0.62418(14) 0.0462(4) Uani d . 1
C C2 0.4491(2) -0.0730(2) 0.68415(14) 0.0478(4) Uani d . 1
C C3 0.5915(2) -0.1377(2) 0.75712(15) 0.0498(5) Uani d . 1
C C4 0.6854(2) -0.0196(2) 0.73558(15) 0.0481(4) Uani d . 1
C C5 0.8351(2) -0.0030(2) 0.78157(15) 0.0498(5) Uani d . 1
H H5 0.8893 -0.0913 0.8374 0.06 Uiso calc R 1
C C6 0.9023(2) 0.1275(2) 0.75108(16) 0.0531(5) Uani d . 1
H H6 0.8488 0.2135 0.6936 0.064 Uiso calc R 1
C C7 1.0501(2) 0.1523(2) 0.79683(15) 0.0489(4) Uani d . 1
C C8 1.1458(2) 0.0342(2) 0.88139(16) 0.0598(5) Uani d . 1
H H8 1.116 -0.0658 0.9111 0.072 Uiso calc R 1
C C9 1.2843(3) 0.0638(3) 0.9215(2) 0.0748(7) Uani d . 1
H H9 1.3478 -0.0168 0.9777 0.09 Uiso calc R 1
C C10 1.3300(3) 0.2103(3) 0.8799(2) 0.0794(7) Uani d . 1
H H10 1.4236 0.2294 0.9077 0.095 Uiso calc R 1
C C11 1.2372(3) 0.3281(3) 0.7974(2) 0.0773(7) Uani d . 1
H H11 1.2674 0.428 0.7685 0.093 Uiso calc R 1
C C12 1.0988(3) 0.2990(2) 0.75696(18) 0.0634(6) Uani d . 1
H H12 1.036 0.3806 0.701 0.076 Uiso calc R 1
C C13 0.7820(3) -0.3771(2) 0.8814(2) 0.0724(6) Uani d . 1
H H13A 0.812 -0.3242 0.9279 0.087 Uiso calc R 1
H H13B 0.8757 -0.3783 0.8243 0.087 Uiso calc R 1
C C14 0.7739(3) -0.5465(3) 0.9474(2) 0.0916(9) Uani d . 1
H H14A 0.6969 -0.5466 1.0114 0.137 Uiso calc R 1
H H14B 0.8912 -0.6071 0.9687 0.137 Uiso calc R 1
H H14C 0.7283 -0.5946 0.9046 0.137 Uiso calc R 1
C C15 0.3199(2) -0.1663(2) 0.68137(16) 0.0534(5) Uani d . 1
C C16 0.1146(3) -0.2014(3) 0.5798(2) 0.0708(6) Uani d . 1
H H16A 0.1741 -0.3125 0.594 0.106 Uiso calc R 1
H H16B 0.0733 -0.1584 0.5071 0.106 Uiso calc R 1
H H16C 0.015 -0.1931 0.6313 0.106 Uiso calc R 1
C C17 0.3561(2) 0.2128(2) 0.54130(16) 0.0515(5) Uani d . 1
C C18 0.3410(3) 0.4695(2) 0.4141(2) 0.0817(7) Uani d . 1
H H18A 0.3137 0.4367 0.3565 0.122 Uiso calc R 1
H H18B 0.4116 0.5492 0.3844 0.122 Uiso calc R 1
H H18C 0.2324 0.5143 0.4479 0.122 Uiso calc R 1
N N1 0.6195(2) -0.2883(2) 0.83366(16) 0.0742(6) Uani d . 1
O O1 0.60740(14) 0.11333(13) 0.65328(10) 0.0479(3) Uani d . 1
O O2 0.20954(19) 0.21669(18) 0.52121(14) 0.0846(6) Uani d . 1
O O3 0.43951(17) 0.33142(14) 0.49437(12) 0.0686(5) Uani d . 1
O O4 0.2979(2) -0.28477(18) 0.75497(13) 0.0838(5) Uani d . 1
O O5 0.23681(16) -0.11152(15) 0.59040(11) 0.0609(4) Uani d . 1
H H1 0.537(3) -0.336(2) 0.8373(17) 0.064(6) Uiso d . 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 0 '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 0.006 '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
C2 C1 O1 110.18(14)
C2 C1 C17 134.44(15)
O1 C1 C17 115.28(15)
C1 C2 C3 106.67(15)
C1 C2 C15 130.78(15)
C3 C2 C15 122.55(15)
C4 C3 N1 129.04(16)
C4 C3 C2 106.41(15)
N1 C3 C2 124.54(16)
C3 C4 O1 109.05(14)
C3 C4 C5 134.99(16)
O1 C4 C5 115.89(15)
C6 C5 C4 125.55(16)
C6 C5 H5 117.2
C4 C5 H5 117.2
C5 C6 C7 127.77(16)
C5 C6 H6 116.1
C7 C6 H6 116.1
C12 C7 C8 117.15(17)
C12 C7 C6 119.89(16)
C8 C7 C6 122.95(17)
C9 C8 C7 120.62(19)
C9 C8 H8 119.7
C7 C8 H8 119.7
C10 C9 C8 120.87(19)
C10 C9 H9 119.6
C8 C9 H9 119.6
C11 C10 C9 119.44(19)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C12 119.9(2)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C7 122.05(19)
C11 C12 H12 119
C7 C12 H12 119
N1 C13 C14 112.23(19)
N1 C13 H13A 109.2
C14 C13 H13A 109.2
N1 C13 H13B 109.2
C14 C13 H13B 109.2
H13A C13 H13B 107.9
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 O5 123.50(17)
O4 C15 C2 122.64(17)
O5 C15 C2 113.82(16)
O5 C16 H16A 109.5
O5 C16 H16B 109.5
H16A C16 H16B 109.5
O5 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O2 C17 O3 123.65(16)
O2 C17 C1 124.69(17)
O3 C17 C1 111.61(15)
O3 C18 H18A 109.5
O3 C18 H18B 109.5
H18A C18 H18B 109.5
O3 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C3 N1 C13 126.15(18)
C3 N1 H1 112.2(13)
C13 N1 H1 119.6(13)
C1 O1 C4 107.68(13)
C17 O3 C18 115.27(15)
C15 O5 C16 116.89(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.357(2)
C1 O1 1.358(2)
C1 C17 1.477(2)
C2 C3 1.432(2)
C2 C15 1.474(2)
C3 C4 1.371(2)
C3 N1 1.373(2)
C4 O1 1.378(2)
C4 C5 1.438(2)
C5 C6 1.326(3)
C5 H5 0.93
C6 C7 1.457(2)
C6 H6 0.93
C7 C12 1.379(3)
C7 C8 1.390(2)
C8 C9 1.375(3)
C8 H8 0.93
C9 C10 1.368(3)
C9 H9 0.93
C10 C11 1.363(3)
C10 H10 0.93
C11 C12 1.375(3)
C11 H11 0.93
C12 H12 0.93
C13 N1 1.410(3)
C13 C14 1.494(3)
C13 H13A 0.97
C13 H13B 0.97
C14 H14A 0.96
C14 H14B 0.96
C14 H14C 0.96
C15 O4 1.204(2)
C15 O5 1.310(2)
C16 O5 1.441(2)
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
C17 O2 1.191(2)
C17 O3 1.320(2)
C18 O3 1.446(2)
C18 H18A 0.96
C18 H18B 0.96
C18 H18C 0.96
N1 H1 0.84(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O4 0.85(2) 2.14(2) 2.813(3) 136.4(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654981
