#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227751.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227751
loop_
_publ_author_name
'Mu, Shuai'
'Yang, Miao'
'Liu, Deng-Ke'
'Liu, Chang-Xiao'
_publ_section_title
;
 1-[4-(4-Nitrophenyl)piperazin-1-yl]-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone
;
_journal_coeditor_code           KP2278
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2762
_journal_paper_doi               10.1107/S1600536810039085
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H22 N4 O3 S'
_chemical_formula_moiety         'C19 H22 N4 O3 S'
_chemical_formula_sum            'C19 H22 N4 O3 S'
_chemical_formula_weight         386.47
_chemical_name_systematic
;
1-[4-(4-Nitrophenyl)piperazin-1-yl]-2-(4,5,6,7-
tetrahydrothieno[3,2-c]pyridin-5-yl)ethanone
;
_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
_cell_angle_alpha                84.101(8)
_cell_angle_beta                 83.385(9)
_cell_angle_gamma                74.635(6)
_cell_formula_units_Z            2
_cell_length_a                   6.1315(7)
_cell_length_b                   8.8552(10)
_cell_length_c                   17.025(2)
_cell_measurement_reflns_used    2732
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.2
_cell_volume                     882.89(18)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10552
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.262
_refine_ls_extinction_coef       0.019(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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0316
_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)+(0.0455P)²+0.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                3402
_reflns_number_total             4169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2278.cif
_cod_data_source_block           I
_cod_original_cell_volume        882.87(18)
_cod_database_code               2227751
_cod_database_fobs_code          2227751
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
S S1 0.30943(5) 0.92591(3) -0.249539(17) 0.01923(11) Uani d . 1 . .
O O1 -0.12392(14) 0.78988(11) 0.05647(6) 0.0249(2) Uani d . 1 . .
O O2 1.01128(18) 0.15750(13) 0.58507(6) 0.0376(3) Uani d . 1 . .
O O3 0.7589(2) 0.02733(13) 0.58411(7) 0.0451(3) Uani d . 1 . .
N N1 0.22099(16) 0.69145(11) -0.00851(6) 0.0145(2) Uani d . 1 . .
N N2 0.32167(16) 0.71481(11) 0.16167(6) 0.0148(2) Uani d . 1 . .
N N3 0.44060(16) 0.56269(11) 0.31518(6) 0.0156(2) Uani d . 1 . .
N N4 0.8425(2) 0.13723(14) 0.55919(7) 0.0275(3) Uani d . 1 . .
C C1 0.0996(2) 0.85073(14) -0.27522(7) 0.0208(3) Uani d . 1 . .
H H1 0.0370 0.8743 -0.3249 0.025 Uiso calc R 1 . .
C C2 0.0340(2) 0.75339(14) -0.21584(7) 0.0183(2) Uani d . 1 . .
H H2 -0.0804 0.7006 -0.2193 0.022 Uiso calc R 1 . .
C C3 0.15476(19) 0.73858(13) -0.14760(7) 0.0147(2) Uani d . 1 . .
C C4 0.31018(19) 0.82610(13) -0.15692(7) 0.0147(2) Uani d . 1 . .
C C5 0.45773(19) 0.83687(14) -0.09431(7) 0.0162(2) Uani d . 1 . .
H H5A 0.3991 0.9385 -0.0700 0.019 Uiso calc R 1 . .
H H5B 0.6148 0.8302 -0.1181 0.019 Uiso calc R 1 . .
C C6 0.45572(19) 0.70088(13) -0.03118(7) 0.0156(2) Uani d . 1 . .
H H6A 0.5467 0.6011 -0.0523 0.019 Uiso calc R 1 . .
H H6B 0.5245 0.7176 0.0160 0.019 Uiso calc R 1 . .
C C7 0.1199(2) 0.64098(14) -0.07174(7) 0.0163(2) Uani d . 1 . .
H H7A -0.0446 0.6535 -0.0570 0.020 Uiso calc R 1 . .
H H7B 0.1916 0.5287 -0.0792 0.020 Uiso calc R 1 . .
C C8 0.08392(19) 0.77300(13) 0.04926(7) 0.0161(2) Uani d . 1 . .
C C9 0.1956(2) 0.83986(14) 0.10806(7) 0.0171(2) Uani d . 1 . .
H H9A 0.3008 0.8981 0.0788 0.021 Uiso calc R 1 . .
H H9B 0.0775 0.9147 0.1396 0.021 Uiso calc R 1 . .
C C10 0.4469(2) 0.78077(14) 0.21157(7) 0.0173(2) Uani d . 1 . .
H H10A 0.3387 0.8607 0.2433 0.021 Uiso calc R 1 . .
H H10B 0.5515 0.8332 0.1775 0.021 Uiso calc R 1 . .
C C11 0.5819(2) 0.65394(14) 0.26673(7) 0.0181(2) Uani d . 1 . .
H H11A 0.7032 0.5820 0.2349 0.022 Uiso calc R 1 . .
H H11B 0.6556 0.7033 0.3022 0.022 Uiso calc R 1 . .
C C12 0.2908(2) 0.51145(14) 0.26835(7) 0.0172(2) Uani d . 1 . .
H H12A 0.1800 0.4685 0.3047 0.021 Uiso calc R 1 . .
H H12B 0.3824 0.4263 0.2358 0.021 Uiso calc R 1 . .
C C13 0.1640(2) 0.64430(14) 0.21457(7) 0.0177(2) Uani d . 1 . .
H H13A 0.0697 0.6039 0.1826 0.021 Uiso calc R 1 . .
H H13B 0.0615 0.7254 0.2471 0.021 Uiso calc R 1 . .
C C14 0.5398(2) 0.45722(13) 0.37518(7) 0.0157(2) Uani d . 1 . .
C C15 0.7310(2) 0.47506(14) 0.40870(7) 0.0194(3) Uani d . 1 . .
H H15 0.7935 0.5608 0.3898 0.023 Uiso calc R 1 . .
C C16 0.8282(2) 0.37062(15) 0.46814(7) 0.0212(3) Uani d . 1 . .
H H16 0.9579 0.3837 0.4895 0.025 Uiso calc R 1 . .
C C17 0.7371(2) 0.24656(14) 0.49676(7) 0.0207(3) Uani d . 1 . .
C C18 0.5485(2) 0.22540(14) 0.46630(7) 0.0214(3) Uani d . 1 . .
H H18 0.4861 0.1404 0.4867 0.026 Uiso calc R 1 . .
C C19 0.4521(2) 0.32864(14) 0.40612(7) 0.0194(3) Uani d . 1 . .
H H19 0.3237 0.3131 0.3849 0.023 Uiso calc R 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
C1 S1 C4 . . 92.11(6) ?
C8 N1 C7 . . 119.36(10) ?
C8 N1 C6 . . 123.35(10) ?
C7 N1 C6 . . 113.03(9) ?
C13 N2 C10 . . 107.24(9) ?
C13 N2 C9 . . 110.12(9) ?
C10 N2 C9 . . 109.88(9) ?
C14 N3 C12 . . 117.17(9) ?
C14 N3 C11 . . 117.63(9) ?
C12 N3 C11 . . 112.57(9) ?
O2 N4 O3 . . 122.75(11) ?
O2 N4 C17 . . 118.95(11) ?
O3 N4 C17 . . 118.30(11) ?
C2 C1 S1 . . 111.59(9) ?
C2 C1 H1 . . 124.2 ?
S1 C1 H1 . . 124.2 ?
C1 C2 C3 . . 112.85(11) ?
C1 C2 H2 . . 123.6 ?
C3 C2 H2 . . 123.6 ?
C4 C3 C2 . . 112.58(11) ?
C4 C3 C7 . . 121.64(10) ?
C2 C3 C7 . . 125.77(10) ?
C3 C4 C5 . . 124.49(11) ?
C3 C4 S1 . . 110.87(9) ?
C5 C4 S1 . . 124.63(9) ?
C4 C5 C6 . . 108.25(9) ?
C4 C5 H5A . . 110.0 ?
C6 C5 H5A . . 110.0 ?
C4 C5 H5B . . 110.0 ?
C6 C5 H5B . . 110.0 ?
H5A C5 H5B . . 108.4 ?
N1 C6 C5 . . 109.67(9) ?
N1 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
N1 C7 C3 . . 109.44(9) ?
N1 C7 H7A . . 109.8 ?
C3 C7 H7A . . 109.8 ?
N1 C7 H7B . . 109.8 ?
C3 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.2 ?
O1 C8 N1 . . 122.19(11) ?
O1 C8 C9 . . 120.27(11) ?
N1 C8 C9 . . 117.51(10) ?
N2 C9 C8 . . 111.26(9) ?
N2 C9 H9A . . 109.4 ?
C8 C9 H9A . . 109.4 ?
N2 C9 H9B . . 109.4 ?
C8 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
N2 C10 C11 . . 111.11(9) ?
N2 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
N2 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
N3 C11 C10 . . 112.67(10) ?
N3 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
N3 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
N3 C12 C13 . . 112.06(9) ?
N3 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
N3 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
N2 C13 C12 . . 110.96(9) ?
N2 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
N2 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
N3 C14 C15 . . 121.43(11) ?
N3 C14 C19 . . 121.51(11) ?
C15 C14 C19 . . 117.06(11) ?
C16 C15 C14 . . 121.21(11) ?
C16 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
C15 C16 C17 . . 119.90(12) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.89(12) ?
C16 C17 N4 . . 119.13(12) ?
C18 C17 N4 . . 119.98(11) ?
C19 C18 C17 . . 119.43(11) ?
C19 C18 H18 . . 120.3 ?
C17 C18 H18 . . 120.3 ?
C18 C19 C14 . . 121.51(11) ?
C18 C19 H19 . . 119.2 ?
C14 C19 H19 . . 119.2 ?
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
S1 C1 . 1.7127(13) ?
S1 C4 . 1.7265(12) ?
O1 C8 . 1.2362(14) ?
O2 N4 . 1.2317(16) ?
O3 N4 . 1.2327(16) ?
N1 C8 . 1.3524(16) ?
N1 C7 . 1.4638(14) ?
N1 C6 . 1.4685(14) ?
N2 C13 . 1.4628(14) ?
N2 C10 . 1.4637(14) ?
N2 C9 . 1.4690(15) ?
N3 C14 . 1.3900(15) ?
N3 C12 . 1.4662(14) ?
N3 C11 . 1.4674(14) ?
N4 C17 . 1.4491(16) ?
C1 C2 . 1.3558(18) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.4251(16) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3658(16) ?
C3 C7 . 1.5051(16) ?
C4 C5 . 1.5008(16) ?
C5 C6 . 1.5311(16) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.5219(16) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5160(16) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5115(16) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.4125(17) ?
C14 C19 . 1.4140(16) ?
C15 C16 . 1.3746(17) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3818(18) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.3833(18) ?
C18 C19 . 1.3768(17) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
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
C1 H1 O3 1_464 0.95 2.47 3.346(2) 154.0
C5 H5A O1 2_575 0.99 2.56 3.475(2) 153.0
C6 H6B O1 1_655 0.99 2.59 3.420(2) 142.0
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
C4 S1 C1 C2 . . . . -0.24(10) ?
S1 C1 C2 C3 . . . . 0.11(14) ?
C1 C2 C3 C4 . . . . 0.12(15) ?
C1 C2 C3 C7 . . . . 179.31(11) ?
C2 C3 C4 C5 . . . . 178.37(10) ?
C7 C3 C4 C5 . . . . -0.85(17) ?
C2 C3 C4 S1 . . . . -0.30(13) ?
C7 C3 C4 S1 . . . . -179.52(9) ?
C1 S1 C4 C3 . . . . 0.31(9) ?
C1 S1 C4 C5 . . . . -178.36(10) ?
C3 C4 C5 C6 . . . . 16.48(15) ?
S1 C4 C5 C6 . . . . -165.03(8) ?
C8 N1 C6 C5 . . . . -87.64(13) ?
C7 N1 C6 C5 . . . . 68.93(12) ?
C4 C5 C6 N1 . . . . -47.59(12) ?
C8 N1 C7 C3 . . . . 107.55(12) ?
C6 N1 C7 C3 . . . . -50.05(12) ?
C4 C3 C7 N1 . . . . 16.24(15) ?
C2 C3 C7 N1 . . . . -162.88(11) ?
C7 N1 C8 O1 . . . . 9.29(17) ?
C6 N1 C8 O1 . . . . 164.47(11) ?
C7 N1 C8 C9 . . . . -172.84(9) ?
C6 N1 C8 C9 . . . . -17.67(16) ?
C13 N2 C9 C8 . . . . -68.22(12) ?
C10 N2 C9 C8 . . . . 173.88(9) ?
O1 C8 C9 N2 . . . . 106.91(12) ?
N1 C8 C9 N2 . . . . -71.00(13) ?
C13 N2 C10 C11 . . . . 61.22(12) ?
C9 N2 C10 C11 . . . . -179.10(9) ?
C14 N3 C11 C10 . . . . -171.71(10) ?
C12 N3 C11 C10 . . . . 47.41(13) ?
N2 C10 C11 N3 . . . . -54.79(13) ?
C14 N3 C12 C13 . . . . 170.61(10) ?
C11 N3 C12 C13 . . . . -48.32(13) ?
C10 N2 C13 C12 . . . . -62.45(12) ?
C9 N2 C13 C12 . . . . 178.02(9) ?
N3 C12 C13 N2 . . . . 56.93(13) ?
C12 N3 C14 C15 . . . . 162.26(10) ?
C11 N3 C14 C15 . . . . 23.17(16) ?
C12 N3 C14 C19 . . . . -18.64(16) ?
C11 N3 C14 C19 . . . . -157.73(11) ?
N3 C14 C15 C16 . . . . 179.86(11) ?
C19 C14 C15 C16 . . . . 0.72(18) ?
C14 C15 C16 C17 . . . . -0.80(19) ?
C15 C16 C17 C18 . . . . 0.11(19) ?
C15 C16 C17 N4 . . . . 179.73(11) ?
O2 N4 C17 C16 . . . . -0.17(18) ?
O3 N4 C17 C16 . . . . 179.92(13) ?
O2 N4 C17 C18 . . . . 179.45(12) ?
O3 N4 C17 C18 . . . . -0.46(19) ?
C16 C17 C18 C19 . . . . 0.64(19) ?
N4 C17 C18 C19 . . . . -178.97(11) ?
C17 C18 C19 C14 . . . . -0.72(19) ?
N3 C14 C19 C18 . . . . -179.10(11) ?
C15 C14 C19 C18 . . . . 0.05(18) ?
