#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/54/2215437.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_2215437
loop_
_publ_author_name
'Qing-Yun Ren'
'Hong-Wu He'
'Chuan-Fei Jin'
'Yu-Cheng Gu'
_publ_section_title
;
 Ethyl 4-amino-5-cyano-6-[(2-hydroxyethyl)amino]-2-methylnicotinate
;
_journal_coeditor_code           CV2296
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4015
_journal_page_last               o4015
_journal_paper_doi               10.1107/S1600536807043383
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H16 N4 O3'
_chemical_formula_moiety         'C12 H16 N4 O3'
_chemical_formula_sum            'C12 H16 N4 O3'
_chemical_formula_weight         264.29
_chemical_name_systematic
;
Ethyl 4-amino-5-cyano-6-[(2-hydroxyethyl)amino]-2-methylnicotinate
;
_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                79.720(2)
_cell_angle_beta                 77.381(2)
_cell_angle_gamma                64.657(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8350(7)
_cell_length_b                   9.1368(9)
_cell_length_c                   10.3272(10)
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      3.24
_cell_volume                     648.97(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0432
_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       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4521
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0581
_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)+(0.0955P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1723
_reflns_number_gt                1991
_reflns_number_total             2767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2296.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 1'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2215437
_cod_database_fobs_code          2215437
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
C C1 0.4786(3) 0.2753(2) 0.45970(17) 0.0404(4) Uani d . 1
C C2 0.6483(2) 0.1345(2) 0.43570(17) 0.0372(4) Uani d . 1
C C3 0.7156(2) 0.0230(2) 0.54871(17) 0.0359(4) Uani d . 1
C C4 0.6070(2) 0.0620(2) 0.67547(17) 0.0377(4) Uani d . 1
C C5 0.4355(2) 0.2018(2) 0.68772(17) 0.0362(4) Uani d . 1
C C6 0.3927(3) 0.4091(3) 0.3547(2) 0.0642(7) Uani d . 1
H H6A 0.3536 0.3671 0.2930 0.096 Uiso calc R 1
H H6B 0.4861 0.4498 0.3080 0.096 Uiso calc R 1
H H6C 0.2837 0.4956 0.3963 0.096 Uiso calc R 1
C C7 0.6634(3) -0.0413(2) 0.79306(18) 0.0416(5) Uani d . 1
C C8 0.7589(3) 0.0936(2) 0.30234(18) 0.0419(5) Uani d . 1
C C9 0.7834(3) 0.1527(2) 0.06883(18) 0.0508(5) Uani d . 1
H H9A 0.7946 0.0472 0.0532 0.061 Uiso calc R 1
H H9B 0.9111 0.1486 0.0606 0.061 Uiso calc R 1
C C10 0.6766(3) 0.2811(3) -0.0303(2) 0.0607(6) Uani d . 1
H H10A 0.5483 0.2884 -0.0181 0.091 Uiso calc R 1
H H10B 0.7395 0.2536 -0.1188 0.091 Uiso calc R 1
H H10C 0.6734 0.3839 -0.0176 0.091 Uiso calc R 1
C C11 0.1222(3) 0.3504(2) 0.8233(2) 0.0510(5) Uani d . 1
H H11A 0.0591 0.3219 0.9096 0.061 Uiso calc R 1
H H11B 0.0634 0.3361 0.7558 0.061 Uiso calc R 1
C C12 0.0869(4) 0.5254(3) 0.8139(2) 0.0636(6) Uani d . 1
H H12A -0.0431 0.5853 0.8561 0.076 Uiso calc R 1
H H12B 0.1725 0.5358 0.8634 0.076 Uiso calc R 1
N N1 0.3761(2) 0.30703(18) 0.58156(14) 0.0422(4) Uani d . 1
N N2 0.8725(2) -0.11440(19) 0.53691(17) 0.0473(4) Uani d D 1
H H2B 0.928(3) -0.122(2) 0.4515(16) 0.057 Uiso d D 1
H H2A 0.900(3) -0.174(2) 0.6103(17) 0.057 Uiso d D 1
N N3 0.7004(3) -0.1181(2) 0.89125(17) 0.0560(5) Uani d . 1
N N4 0.3234(2) 0.23730(19) 0.80702(16) 0.0461(4) Uani d . 1
H H4A 0.372(3) 0.164(3) 0.866(2) 0.055 Uiso d . 1
O O1 0.9108(2) -0.02184(18) 0.28168(15) 0.0628(5) Uani d . 1
O O2 0.67814(19) 0.19305(16) 0.20107(12) 0.0496(4) Uani d . 1
O O3 0.1129(3) 0.59692(18) 0.68257(16) 0.0728(5) Uani d D 1
H H3A 0.111(5) 0.532(3) 0.633(3) 0.109 Uiso d 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 0.0000 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
N1 C1 C2 123.25(16)
N1 C1 C6 111.78(16)
C2 C1 C6 124.95(16)
C1 C2 C3 117.65(15)
C1 C2 C8 124.27(16)
C3 C2 C8 118.08(16)
N2 C3 C4 119.91(16)
N2 C3 C2 122.47(16)
C4 C3 C2 117.61(15)
C5 C4 C3 120.14(15)
C5 C4 C7 118.39(15)
C3 C4 C7 121.43(15)
N1 C5 N4 117.00(15)
N1 C5 C4 121.62(15)
N4 C5 C4 121.38(16)
C1 C6 H6A 109.5
C1 C6 H6B 109.5
H6A C6 H6B 109.5
C1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N3 C7 C4 176.31(18)
O1 C8 O2 120.50(17)
O1 C8 C2 124.55(18)
O2 C8 C2 114.94(16)
O2 C9 C10 107.96(16)
O2 C9 H9A 110.1
C10 C9 H9A 110.1
O2 C9 H9B 110.1
C10 C9 H9B 110.1
H9A C9 H9B 108.4
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
N4 C11 C12 115.13(18)
N4 C11 H11A 108.5
C12 C11 H11A 108.5
N4 C11 H11B 108.5
C12 C11 H11B 108.5
H11A C11 H11B 107.5
O3 C12 C11 114.25(18)
O3 C12 H12A 108.7
C11 C12 H12A 108.7
O3 C12 H12B 108.7
C11 C12 H12B 108.7
H12A C12 H12B 107.6
C1 N1 C5 119.62(15)
C3 N2 H2B 110.1(13)
C3 N2 H2A 115.4(15)
H2B N2 H2A 134(2)
C5 N4 C11 123.93(15)
C5 N4 H4A 109.6(16)
C11 N4 H4A 123.3(16)
C8 O2 C9 115.70(15)
C12 O3 H3A 105(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.342(2)
C1 C2 1.410(2)
C1 C6 1.504(2)
C2 C3 1.436(2)
C2 C8 1.474(2)
C3 N2 1.330(2)
C3 C4 1.409(2)
C4 C5 1.403(2)
C4 C7 1.424(2)
C5 N1 1.344(2)
C5 N4 1.349(2)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 N3 1.142(2)
C8 O1 1.212(2)
C8 O2 1.333(2)
C9 O2 1.452(2)
C9 C10 1.493(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 N4 1.461(2)
C11 C12 1.490(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O3 1.409(3)
C12 H12A 0.9700
C12 H12B 0.9700
N2 H2B 0.895(15)
N2 H2A 0.859(15)
N4 H4A 0.84(2)
O3 H3A 0.861(17)
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
_geom_hbond_publ_flag
O3 H3A N1 . 0.861(17) 2.25(3) 2.780(2) 120(3) yes
N2 H2B O1 . 0.895(15) 1.832(17) 2.613(2) 144.6(19) yes
N4 H4A N3 2_657 0.84(2) 2.45(2) 3.105(2) 136.1(19) yes
N2 H2A O3 1_645 0.859(15) 2.175(18) 2.887(2) 140(2) yes
C12 H12A N3 1_465 0.97 2.62 3.442(3) 142.2 ?
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
N1 C1 C2 C3 -1.8(3)
C6 C1 C2 C3 176.79(18)
N1 C1 C2 C8 177.27(16)
C6 C1 C2 C8 -4.2(3)
C1 C2 C3 N2 179.06(17)
C8 C2 C3 N2 -0.1(3)
C1 C2 C3 C4 0.2(2)
C8 C2 C3 C4 -178.96(15)
N2 C3 C4 C5 -176.27(17)
C2 C3 C4 C5 2.7(2)
N2 C3 C4 C7 1.3(3)
C2 C3 C4 C7 -179.74(15)
C3 C4 C5 N1 -4.2(3)
C7 C4 C5 N1 178.16(15)
C3 C4 C5 N4 176.30(16)
C7 C4 C5 N4 -1.4(3)
C1 C2 C8 O1 175.22(19)
C3 C2 C8 O1 -5.7(3)
C1 C2 C8 O2 -5.8(3)
C3 C2 C8 O2 173.23(14)
N4 C11 C12 O3 78.5(3)
C2 C1 N1 C5 0.4(3)
C6 C1 N1 C5 -178.30(17)
N4 C5 N1 C1 -177.88(16)
C4 C5 N1 C1 2.6(3)
N1 C5 N4 C11 18.9(3)
C4 C5 N4 C11 -161.55(17)
C12 C11 N4 C5 -83.0(2)
O1 C8 O2 C9 0.1(3)
C2 C8 O2 C9 -178.88(15)
C10 C9 O2 C8 -177.24(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123403
2 PubChem 139073099
