#------------------------------------------------------------------------------
#$Date: 2021-04-10 08:22:43 +0300 (Sat, 10 Apr 2021) $
#$Revision: 264041 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/16/1561636.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_1561636
loop_
_publ_author_name
'Khanum, Ghazala'
'Fatima, Aysha'
'Sharma, Pooja'
'Srivastava, S. K.'
'Butcher, Ray J.'
_publ_section_title
;
 Ethyl 2-amino-4-methylthiophene-3-carboxylate
;
_journal_coeditor_code           BT4112
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x210351
_journal_paper_doi               10.1107/S2414314621003515
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C8 H11 N O2 S'
_chemical_formula_moiety         'C8 H11 N O2 S'
_chemical_formula_sum            'C8 H11 N O2 S'
_chemical_formula_weight         185.24
_chemical_name_systematic
;
Ethyl 2-amino-4-methylthiophene-3-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                91.602(12)
_cell_angle_beta                 104.301(13)
_cell_angle_gamma                101.729(13)
_cell_formula_units_Z            4
_cell_length_a                   7.664(3)
_cell_length_b                   9.876(3)
_cell_length_c                   13.018(5)
_cell_measurement_reflns_used    9004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.55
_cell_volume                     931.7(6)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27589
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.113
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.388
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0812P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                3845
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4112sup1.cif
_cod_data_source_block           I
_cod_database_code               1561636
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.867
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.57912(8) 0.63040(5) 0.90873(4) 0.05608(17) Uani d 1 . .
O O1A 0.5956(2) 1.07513(14) 0.82938(11) 0.0598(4) Uani d 1 . .
O O2A 0.77241(18) 1.13164(13) 0.99478(10) 0.0469(3) Uani d 1 . .
N N1A 0.4678(3) 0.7995(2) 0.76263(15) 0.0611(5) Uani d 1 . .
H H1AA 0.478(4) 0.878(3) 0.741(2) 0.074(8) Uiso d 1 . .
H H1AB 0.420(4) 0.728(3) 0.718(2) 0.067(7) Uiso d 1 . .
C C1A 0.5667(3) 0.79097(18) 0.86174(15) 0.0434(4) Uani d 1 . .
C C2A 0.6638(2) 0.89702(17) 0.93919(13) 0.0394(4) Uani d 1 . .
C C3A 0.7481(2) 0.84624(19) 1.03824(14) 0.0429(4) Uani d 1 . .
C C4A 0.7121(3) 0.7062(2) 1.03180(17) 0.0535(5) Uani d 1 . .
H H4AA 0.754788 0.655468 1.088165 0.064 Uiso calc 1 . .
C C5A 0.8619(3) 0.9325(2) 1.13746(16) 0.0580(5) Uani d 1 . .
H H5AA 0.899385 0.872987 1.191859 0.087 Uiso calc 1 . .
H H5AB 0.790195 0.990278 1.160998 0.087 Uiso calc 1 . .
H H5AC 0.969117 0.989811 1.123237 0.087 Uiso calc 1 . .
C C6A 0.6715(2) 1.03954(17) 0.91494(14) 0.0400(4) Uani d 1 . .
C C7A 0.7865(3) 1.27623(18) 0.97679(16) 0.0501(4) Uani d 1 . .
H H7AA 0.664931 1.297311 0.957187 0.060 Uiso calc 1 . .
H H7AB 0.845948 1.299239 0.919940 0.060 Uiso calc 1 . .
C C8A 0.8989(3) 1.3566(2) 1.07851(18) 0.0607(5) Uani d 1 . .
H H8AA 0.910249 1.454059 1.070404 0.091 Uiso calc 1 . .
H H8AB 1.019220 1.335704 1.096380 0.091 Uiso calc 1 . .
H H8AC 0.839418 1.331695 1.134225 0.091 Uiso calc 1 . .
S S1B 0.35148(12) 0.08122(6) 0.57884(5) 0.0809(3) Uani d 1 . .
O O1B 0.3541(2) 0.53445(14) 0.63773(11) 0.0620(4) Uani d 1 . .
O O2B 0.2205(2) 0.52307(14) 0.46392(11) 0.0538(3) Uani d 1 . .
N N1B 0.4376(3) 0.2976(2) 0.72151(14) 0.0639(5) Uani d 1 . .
H H1BA 0.451(3) 0.381(3) 0.7357(18) 0.057(7) Uiso d 1 . .
H H1BB 0.484(4) 0.242(3) 0.765(2) 0.076(8) Uiso d 1 . .
C C1B 0.3661(3) 0.25098(19) 0.61927(15) 0.0474(4) Uani d 1 . .
C C2B 0.2967(3) 0.32322(18) 0.53404(13) 0.0425(4) Uani d 1 . .
C C3B 0.2320(3) 0.2374(2) 0.43493(16) 0.0564(5) Uani d 1 . .
C C4B 0.2549(5) 0.1078(3) 0.4495(2) 0.0824(8) Uani d 1 . .
H H4BA 0.221258 0.038177 0.394211 0.099 Uiso calc 1 . .
C C5B 0.1488(4) 0.2818(3) 0.32835(17) 0.0748(7) Uani d 1 . .
H H5BA 0.121058 0.205434 0.275478 0.112 Uiso calc 1 . .
H H5BB 0.234517 0.357479 0.311217 0.112 Uiso calc 1 . .
H H5BC 0.037419 0.311113 0.329922 0.112 Uiso calc 1 . .
C C6B 0.2961(3) 0.46767(18) 0.55163(14) 0.0424(4) Uani d 1 . .
C C7B 0.2082(3) 0.6659(2) 0.47361(19) 0.0609(5) Uani d 1 . .
H H7BA 0.330234 0.725322 0.498848 0.073 Uiso calc 1 . .
H H7BB 0.136218 0.679395 0.523229 0.073 Uiso calc 1 . .
C C8B 0.1157(4) 0.6988(3) 0.3643(2) 0.0809(8) Uani d 1 . .
H H8BA 0.089268 0.789501 0.367982 0.121 Uiso calc 1 . .
H H8BB 0.002774 0.631283 0.336545 0.121 Uiso calc 1 . .
H H8BC 0.195895 0.696714 0.318332 0.121 Uiso calc 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'
S S 0.1246 0.1234 '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
C4A S1A C1A . . 91.37(9) y
C6A O2A C7A . . 117.21(14) ?
C1A N1A H1AA . . 116.2(19) ?
C1A N1A H1AB . . 122.2(17) ?
H1AA N1A H1AB . . 120(2) ?
N1A C1A C2A . . 128.91(17) ?
N1A C1A S1A . . 119.95(15) ?
C2A C1A S1A . . 111.12(14) ?
C1A C2A C6A . . 119.56(16) ?
C1A C2A C3A . . 112.69(15) ?
C6A C2A C3A . . 127.75(16) ?
C4A C3A C2A . . 111.36(17) ?
C4A C3A C5A . . 122.25(18) ?
C2A C3A C5A . . 126.40(16) ?
C3A C4A S1A . . 113.46(15) ?
C3A C4A H4AA . . 123.3 ?
S1A C4A H4AA . . 123.3 ?
C3A C5A H5AA . . 109.5 ?
C3A C5A H5AB . . 109.5 ?
H5AA C5A H5AB . . 109.5 ?
C3A C5A H5AC . . 109.5 ?
H5AA C5A H5AC . . 109.5 ?
H5AB C5A H5AC . . 109.5 ?
O1A C6A O2A . . 121.81(16) ?
O1A C6A C2A . . 124.29(16) ?
O2A C6A C2A . . 113.89(15) ?
O2A C7A C8A . . 106.65(16) ?
O2A C7A H7AA . . 110.4 ?
C8A C7A H7AA . . 110.4 ?
O2A C7A H7AB . . 110.4 ?
C8A C7A H7AB . . 110.4 ?
H7AA C7A H7AB . . 108.6 ?
C7A C8A H8AA . . 109.5 ?
C7A C8A H8AB . . 109.5 ?
H8AA C8A H8AB . . 109.5 ?
C7A C8A H8AC . . 109.5 ?
H8AA C8A H8AC . . 109.5 ?
H8AB C8A H8AC . . 109.5 ?
C4B S1B C1B . . 91.28(11) y
C6B O2B C7B . . 117.81(16) ?
C1B N1B H1BA . . 116.5(17) ?
C1B N1B H1BB . . 118.1(18) ?
H1BA N1B H1BB . . 124(2) ?
N1B C1B C2B . . 128.53(18) ?
N1B C1B S1B . . 120.36(15) ?
C2B C1B S1B . . 111.12(14) ?
C1B C2B C6B . . 119.66(16) ?
C1B C2B C3B . . 112.43(17) ?
C6B C2B C3B . . 127.92(17) ?
C4B C3B C2B . . 111.01(19) ?
C4B C3B C5B . . 122.6(2) ?
C2B C3B C5B . . 126.34(19) ?
C3B C4B S1B . . 114.16(17) ?
C3B C4B H4BA . . 122.9 ?
S1B C4B H4BA . . 122.9 ?
C3B C5B H5BA . . 109.5 ?
C3B C5B H5BB . . 109.5 ?
H5BA C5B H5BB . . 109.5 ?
C3B C5B H5BC . . 109.5 ?
H5BA C5B H5BC . . 109.5 ?
H5BB C5B H5BC . . 109.5 ?
O1B C6B O2B . . 121.96(17) ?
O1B C6B C2B . . 124.56(17) ?
O2B C6B C2B . . 113.46(16) ?
O2B C7B C8B . . 106.1(2) ?
O2B C7B H7BA . . 110.5 ?
C8B C7B H7BA . . 110.5 ?
O2B C7B H7BB . . 110.5 ?
C8B C7B H7BB . . 110.5 ?
H7BA C7B H7BB . . 108.7 ?
C7B C8B H8BA . . 109.5 ?
C7B C8B H8BB . . 109.5 ?
H8BA C8B H8BB . . 109.5 ?
C7B C8B H8BC . . 109.5 ?
H8BA C8B H8BC . . 109.5 ?
H8BB C8B H8BC . . 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
S1A C4A . 1.727(2) y
S1A C1A . 1.7277(19) y
O1A C6A . 1.220(2) y
O2A C6A . 1.330(2) y
O2A C7A . 1.440(2) y
N1A C1A . 1.340(3) y
N1A H1AA . 0.83(3) ?
N1A H1AB . 0.86(3) ?
C1A C2A . 1.386(3) ?
C2A C6A . 1.444(2) ?
C2A C3A . 1.445(2) ?
C3A C4A . 1.350(3) ?
C3A C5A . 1.495(3) ?
C4A H4AA . 0.9300 ?
C5A H5AA . 0.9600 ?
C5A H5AB . 0.9600 ?
C5A H5AC . 0.9600 ?
C7A C8A . 1.492(3) ?
C7A H7AA . 0.9700 ?
C7A H7AB . 0.9700 ?
C8A H8AA . 0.9600 ?
C8A H8AB . 0.9600 ?
C8A H8AC . 0.9600 ?
S1B C4B . 1.715(3) y
S1B C1B . 1.716(2) y
O1B C6B . 1.217(2) y
O2B C6B . 1.333(2) y
O2B C7B . 1.437(2) y
N1B C1B . 1.337(3) y
N1B H1BA . 0.82(3) ?
N1B H1BB . 0.87(3) ?
C1B C2B . 1.389(2) ?
C2B C6B . 1.440(2) ?
C2B C3B . 1.443(3) ?
C3B C4B . 1.339(3) ?
C3B C5B . 1.495(3) ?
C4B H4BA . 0.9300 ?
C5B H5BA . 0.9600 ?
C5B H5BB . 0.9600 ?
C5B H5BC . 0.9600 ?
C7B C8B . 1.502(3) ?
C7B H7BA . 0.9700 ?
C7B H7BB . 0.9700 ?
C8B H8BA . 0.9600 ?
C8B H8BB . 0.9600 ?
C8B H8BC . 0.9600 ?
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
N1B H1BA O1B . 0.82(3) 2.14(3) 2.734(3) 130(2) yes
N1B H1BB O1A 1_545 0.87(3) 2.10(3) 2.946(3) 163(2) yes
N1A H1AA S1B 1_565 0.83(3) 3.07(3) 3.819(2) 151(2) yes
N1A H1AA O1A . 0.83(3) 2.14(3) 2.736(3) 129(2) yes
N1A H1AB O1B . 0.86(3) 2.05(3) 2.897(3) 165(2) yes
C7A H7AA S1A 2_677 0.97 3.02 3.736(3) 131.4 yes
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
C4A S1A C1A N1A . . . . -177.88(18) ?
C4A S1A C1A C2A . . . . 0.54(15) ?
N1A C1A C2A C6A . . . . -2.3(3) ?
S1A C1A C2A C6A . . . . 179.41(13) ?
N1A C1A C2A C3A . . . . 177.8(2) ?
S1A C1A C2A C3A . . . . -0.5(2) ?
C1A C2A C3A C4A . . . . 0.1(2) ?
C6A C2A C3A C4A . . . . -179.77(18) ?
C1A C2A C3A C5A . . . . -179.96(18) ?
C6A C2A C3A C5A . . . . 0.2(3) ?
C2A C3A C4A S1A . . . . 0.3(2) ?
C5A C3A C4A S1A . . . . -179.62(16) ?
C1A S1A C4A C3A . . . . -0.52(17) ?
C7A O2A C6A O1A . . . . 0.9(3) ?
C7A O2A C6A C2A . . . . -179.88(16) ?
C1A C2A C6A O1A . . . . 0.7(3) ?
C3A C2A C6A O1A . . . . -179.46(18) ?
C1A C2A C6A O2A . . . . -178.48(15) ?
C3A C2A C6A O2A . . . . 1.4(3) ?
C6A O2A C7A C8A . . . . 177.71(17) ?
C4B S1B C1B N1B . . . . -179.6(2) ?
C4B S1B C1B C2B . . . . 0.33(19) ?
N1B C1B C2B C6B . . . . -0.3(3) ?
S1B C1B C2B C6B . . . . 179.78(15) ?
N1B C1B C2B C3B . . . . 179.7(2) ?
S1B C1B C2B C3B . . . . -0.3(2) ?
C1B C2B C3B C4B . . . . 0.0(3) ?
C6B C2B C3B C4B . . . . 180.0(2) ?
C1B C2B C3B C5B . . . . 179.7(2) ?
C6B C2B C3B C5B . . . . -0.3(4) ?
C2B C3B C4B S1B . . . . 0.2(3) ?
C5B C3B C4B S1B . . . . -179.5(2) ?
C1B S1B C4B C3B . . . . -0.3(3) ?
C7B O2B C6B O1B . . . . -0.2(3) ?
C7B O2B C6B C2B . . . . 178.22(17) ?
C1B C2B C6B O1B . . . . 0.4(3) ?
C3B C2B C6B O1B . . . . -179.5(2) ?
C1B C2B C6B O2B . . . . -177.98(17) ?
C3B C2B C6B O2B . . . . 2.1(3) ?
C6B O2B C7B C8B . . . . -179.07(18) ?

_cod_database_fobs_code 1561636
