#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/36/2223652.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_2223652
loop_
_publ_author_name
'Yu, Qun-Di'
'Li, Ke-Xin'
'Liu, Yun-Yu'
_publ_section_title
;
 Ethyl 6-amino-5-cyano-2-methyl-4-propyl-4H-pyran-3-carboxylate
;
_journal_coeditor_code           BT5109
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2862
_journal_paper_doi               10.1107/S1600536809043748
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H18 N2 O3'
_chemical_formula_moiety         'C13 H18 N2 O3'
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.15
_chemical_name_systematic
;
Ethyl 6-amino-5-cyano-2-methyl-4-propyl-4H-pyran-3-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.082(12)
_cell_angle_beta                 107.274(12)
_cell_angle_gamma                103.315(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1172(9)
_cell_length_b                   8.7956(9)
_cell_length_c                   11.2877(19)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.01
_cell_volume                     695.20(19)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX 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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5049
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0460
_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)+(0.0757P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                1577
_reflns_number_total             2826
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5109.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2223652
_cod_database_fobs_code          2223652
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.2429(2) -0.09571(19) 0.63342(17) 0.0444(4) Uani d . 1 . .
C C2 -0.1346(2) -0.18666(19) 0.61071(16) 0.0428(4) Uani d . 1 . .
C C3 -0.2165(2) -0.3640(2) 0.55184(18) 0.0507(5) Uani d . 1 . .
C C4 0.0703(2) -0.10825(19) 0.65363(16) 0.0416(4) Uani d . 1 . .
H H4 0.1012 -0.1530 0.5765 0.050 Uiso calc R 1 . .
C C5 0.1778(2) -0.1557(2) 0.76684(17) 0.0513(5) Uani d . 1 . .
H H5A 0.1418 -0.2774 0.7362 0.062 Uiso calc R 1 . .
H H5B 0.3075 -0.1117 0.7850 0.062 Uiso calc R 1 . .
C C6 0.1500(3) -0.0922(3) 0.8948(2) 0.0716(6) Uani d . 1 . .
H H6A 0.0195 -0.1271 0.8756 0.086 Uiso calc R 1 . .
H H6B 0.1976 0.0298 0.9305 0.086 Uiso calc R 1 . .
C C7 0.2423(4) -0.1545(3) 1.0004(2) 0.1038(9) Uani d . 1 . .
H H7A 0.2186 -0.1102 1.0791 0.156 Uiso calc R 1 . .
H H7B 0.3723 -0.1175 1.0223 0.156 Uiso calc R 1 . .
H H7C 0.1945 -0.2753 0.9666 0.156 Uiso calc R 1 . .
C C8 0.0021(2) 0.1608(2) 0.70345(17) 0.0446(4) Uani d . 1 . .
C C9 0.1207(2) 0.08115(19) 0.69043(16) 0.0404(4) Uani d . 1 . .
C C10 0.0223(3) 0.3431(2) 0.7354(2) 0.0670(6) Uani d . 1 . .
H H10A -0.0868 0.3524 0.6792 0.101 Uiso calc R 1 . .
H H10B 0.1258 0.3989 0.7199 0.101 Uiso calc R 1 . .
H H10C 0.0409 0.3947 0.8274 0.101 Uiso calc R 1 . .
C C11 0.3091(2) 0.1666(2) 0.70545(18) 0.0466(4) Uani d . 1 . .
C C12 0.5617(3) 0.4184(3) 0.7863(2) 0.0737(6) Uani d . 1 . .
H H12A 0.5646 0.4016 0.6984 0.088 Uiso calc R 1 . .
H H12B 0.6491 0.3749 0.8326 0.088 Uiso calc R 1 . .
C C13 0.6091(4) 0.5982(3) 0.8618(3) 0.1117(9) Uani d . 1 . .
H H13A 0.7300 0.6584 0.8713 0.168 Uiso calc R 1 . .
H H13B 0.6061 0.6135 0.9486 0.168 Uiso calc R 1 . .
H H13C 0.5222 0.6403 0.8149 0.168 Uiso calc R 1 . .
N N2 -0.4192(2) -0.1503(2) 0.61418(18) 0.0606(5) Uani d . 1 . .
N N1 -0.2822(2) -0.5075(2) 0.50412(19) 0.0763(6) Uani d . 1 . .
O O3 -0.17565(15) 0.07590(13) 0.68500(12) 0.0530(3) Uani d . 1 . .
O O1 0.39733(18) 0.09129(16) 0.65942(14) 0.0694(4) Uani d . 1 . .
O O2 0.37809(16) 0.33123(15) 0.77399(14) 0.0612(4) Uani d . 1 . .
H H2A -0.472(2) -0.083(2) 0.6160(17) 0.055(5) Uiso d . 1 . .
H H2B -0.485(3) -0.253(3) 0.585(2) 0.062(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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
N2 C1 C2 . . 128.59(16) ?
N2 C1 O3 . . 110.12(13) ?
C2 C1 O3 . . 121.28(15) ?
C1 C2 C3 . . 117.85(15) ?
C1 C2 C4 . . 122.94(14) ?
C3 C2 C4 . . 119.09(12) ?
N1 C3 C2 . . 179.8(2) ?
C2 C4 C9 . . 109.31(11) ?
C2 C4 C5 . . 111.67(13) ?
C9 C4 C5 . . 112.78(13) ?
C2 C4 H4 . . 107.6 ?
C9 C4 H4 . . 107.6 ?
C5 C4 H4 . . 107.6 ?
C6 C5 C4 . . 114.61(13) ?
C6 C5 H5A . . 108.6 ?
C4 C5 H5A . . 108.6 ?
C6 C5 H5B . . 108.6 ?
C4 C5 H5B . . 108.6 ?
H5A C5 H5B . . 107.6 ?
C5 C6 C7 . . 113.67(18) ?
C5 C6 H6A . . 108.8 ?
C7 C6 H6A . . 108.8 ?
C5 C6 H6B . . 108.8 ?
C7 C6 H6B . . 108.8 ?
H6A C6 H6B . . 107.7 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 O3 . . 121.91(14) ?
C9 C8 C10 . . 130.81(16) ?
O3 C8 C10 . . 107.27(12) ?
C8 C9 C11 . . 123.41(14) ?
C8 C9 C4 . . 122.47(15) ?
C11 C9 C4 . . 114.08(12) ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O1 C11 O2 . . 121.58(16) ?
O1 C11 C9 . . 122.36(16) ?
O2 C11 C9 . . 116.06(13) ?
O2 C12 C13 . . 107.97(17) ?
O2 C12 H12A . . 110.1 ?
C13 C12 H12A . . 110.1 ?
O2 C12 H12B . . 110.1 ?
C13 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.4 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 N2 H2A . . 117.1(13) ?
C1 N2 H2B . . 124.7(13) ?
H2A N2 H2B . . 117.0(18) ?
C1 O3 C8 . . 120.17(11) ?
C11 O2 C12 . . 116.81(13) ?
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
C1 N2 . 1.329(2) ?
C1 C2 . 1.350(2) ?
C1 O3 . 1.3638(19) ?
C2 C3 . 1.415(2) ?
C2 C4 . 1.512(2) ?
C3 N1 . 1.145(2) ?
C4 C9 . 1.522(2) ?
C4 C5 . 1.540(2) ?
C4 H4 . 0.9800 ?
C5 C6 . 1.502(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.517(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.333(2) ?
C8 O3 . 1.3862(19) ?
C8 C10 . 1.501(2) ?
C9 C11 . 1.476(2) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O1 . 1.2122(18) ?
C11 O2 . 1.326(2) ?
C12 O2 . 1.456(2) ?
C12 C13 . 1.467(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N2 H2A . 0.805(18) ?
N2 H2B . 0.85(2) ?
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
N2 H2A O1 1_455 0.805(18) 2.088(19) 2.881(2) 168.2(17)
N2 H2B N1 2_446 0.85(2) 2.21(2) 3.035(3) 164.4(17)
