#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233896.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_2233896
loop_
_publ_author_name
'Pan, Yu-Zhen'
'Wang, You-Gui'
'Liu, Jian-Hui'
'Sun, Li-Cheng'
_publ_section_title
;
 10-Ethyl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-10H-phenothiazine
;
_journal_coeditor_code           IS5065
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o649
_journal_paper_doi               10.1107/S160053681200462X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H15 N3 O S'
_chemical_formula_moiety         'C17 H15 N3 O S'
_chemical_formula_sum            'C17 H15 N3 O S'
_chemical_formula_weight         309.38
_chemical_name_systematic
;
10-Ethyl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-10H-phenothiazine
;
_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                84.870(4)
_cell_angle_beta                 82.569(4)
_cell_angle_gamma                63.696(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6752(4)
_cell_length_b                   8.2913(4)
_cell_length_c                   12.9469(8)
_cell_measurement_reflns_used    2708
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.57
_cell_measurement_theta_min      3.04
_cell_volume                     731.91(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'DIAMOND (Brandenburg & Putz, 2004) and SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (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 SMART APEX'
_diffrn_measurement_method       'φ and ω 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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5348
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0393
_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)+(0.0547P)²+0.2148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                2217
_reflns_number_total             2554
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5065.cif
_cod_data_source_block           I
_cod_original_cell_volume        731.92(7)
_cod_database_code               2233896
_cod_database_fobs_code          2233896
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_symmetry_multiplicity
S S1 0.37243(8) 0.17365(6) 0.11098(4) 0.05078(19) Uani d . 1 1
O O1 0.39396(19) 0.69128(15) -0.27750(9) 0.0430(3) Uani d . 1 1
C C12 0.2887(2) 0.3831(2) 0.04285(13) 0.0353(4) Uani d . 1 1
N N1 0.0965(2) 0.54971(18) 0.19818(11) 0.0410(4) Uani d . 1 1
C C10 0.3234(3) 0.5423(2) -0.11819(13) 0.0388(4) Uani d . 1 1
C C6 0.0893(3) 0.3994(2) 0.25572(13) 0.0376(4) Uani d . 1 1
C C7 0.1642(2) 0.5454(2) 0.09210(13) 0.0371(4) Uani d . 1 1
C C1 0.2039(3) 0.2227(2) 0.22245(13) 0.0377(4) Uani d . 1 1
N N2 0.5266(2) 0.3956(2) -0.27726(12) 0.0460(4) Uani d . 1 1
C C13 0.4168(3) 0.5350(2) -0.22376(13) 0.0388(4) Uani d . 1 1
C C11 0.3653(3) 0.3829(2) -0.05932(13) 0.0382(4) Uani d . 1 1
H H11 0.4470 0.2736 -0.0898 0.046 Uiso calc R 1 1
C C9 0.1961(3) 0.7029(2) -0.07199(14) 0.0452(5) Uani d . 1 1
H H9 0.1633 0.8110 -0.1103 0.054 Uiso calc R 1 1
C C5 -0.0285(3) 0.4198(2) 0.34965(14) 0.0450(4) Uani d . 1 1
H H5 -0.1070 0.5351 0.3734 0.054 Uiso calc R 1 1
C C15 0.0098(3) 0.7238(2) 0.24919(15) 0.0454(5) Uani d . 1 1
H H15A 0.0783 0.7936 0.2189 0.054 Uiso calc R 1 1
H H15B 0.0307 0.7016 0.3224 0.054 Uiso calc R 1 1
N N3 0.5841(2) 0.4600(2) -0.37384(12) 0.0477(4) Uani d . 1 1
C C8 0.1174(3) 0.7040(2) 0.03038(14) 0.0453(5) Uani d . 1 1
H H8 0.0307 0.8133 0.0592 0.054 Uiso calc R 1 1
C C2 0.1976(3) 0.0770(2) 0.28143(15) 0.0462(5) Uani d . 1 1
H H2 0.2731 -0.0388 0.2577 0.055 Uiso calc R 1 1
C C14 0.5034(3) 0.6320(2) -0.36985(13) 0.0424(4) Uani d . 1 1
C C4 -0.0320(3) 0.2730(3) 0.40882(15) 0.0498(5) Uani d . 1 1
H H4 -0.1109 0.2908 0.4716 0.060 Uiso calc R 1 1
C C16 -0.2063(3) 0.8351(3) 0.24062(18) 0.0573(6) Uani d . 1 1
H H16A -0.2300 0.8537 0.1685 0.086 Uiso calc R 1 1
H H16B -0.2488 0.9493 0.2713 0.086 Uiso calc R 1 1
H H16C -0.2773 0.7728 0.2766 0.086 Uiso calc R 1 1
C C3 0.0812(3) 0.1007(3) 0.37469(16) 0.0521(5) Uani d . 1 1
H H3 0.0790 0.0020 0.4140 0.063 Uiso calc R 1 1
C C17 0.5164(4) 0.7672(3) -0.44929(15) 0.0558(5) Uani d . 1 1
H H17A 0.5952 0.8184 -0.4272 0.084 Uiso calc R 1 1
H H17B 0.3878 0.8606 -0.4578 0.084 Uiso calc R 1 1
H H17C 0.5748 0.7102 -0.5145 0.084 Uiso calc R 1 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
C1 S1 C12 101.74(8)
C14 O1 C13 102.81(13)
C11 C12 C7 121.19(15)
C11 C12 S1 116.40(12)
C7 C12 S1 122.15(13)
C7 N1 C6 123.14(14)
C7 N1 C15 118.30(14)
C6 N1 C15 118.23(14)
C9 C10 C11 118.04(16)
C9 C10 C13 122.68(16)
C11 C10 C13 119.26(15)
C5 C6 C1 117.04(16)
C5 C6 N1 121.22(15)
C1 C6 N1 121.73(15)
C8 C7 N1 121.38(15)
C8 C7 C12 116.46(15)
N1 C7 C12 122.11(15)
C2 C1 C6 120.68(16)
C2 C1 S1 116.70(13)
C6 C1 S1 122.48(13)
C13 N2 N3 106.45(14)
N2 C13 O1 112.02(15)
N2 C13 C10 128.50(16)
O1 C13 C10 119.47(15)
C12 C11 C10 121.51(15)
C12 C11 H11 119.2
C10 C11 H11 119.2
C8 C9 C10 120.70(16)
C8 C9 H9 119.6
C10 C9 H9 119.6
C4 C5 C6 121.87(17)
C4 C5 H5 119.1
C6 C5 H5 119.1
N1 C15 C16 114.91(16)
N1 C15 H15A 108.5
C16 C15 H15A 108.5
N1 C15 H15B 108.5
C16 C15 H15B 108.5
H15A C15 H15B 107.5
C14 N3 N2 106.14(14)
C9 C8 C7 122.01(16)
C9 C8 H8 119.0
C7 C8 H8 119.0
C3 C2 C1 121.15(17)
C3 C2 H2 119.4
C1 C2 H2 119.4
N3 C14 O1 112.57(15)
N3 C14 C17 129.09(17)
O1 C14 C17 118.33(16)
C3 C4 C5 120.19(17)
C3 C4 H4 119.9
C5 C4 H4 119.9
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C2 C3 C4 119.06(17)
C2 C3 H3 120.5
C4 C3 H3 120.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7541(17)
S1 C12 1.7583(17)
O1 C14 1.362(2)
O1 C13 1.365(2)
C12 C11 1.376(2)
C12 C7 1.409(2)
N1 C7 1.402(2)
N1 C6 1.413(2)
N1 C15 1.472(2)
C10 C9 1.387(2)
C10 C11 1.392(2)
C10 C13 1.452(2)
C6 C5 1.394(2)
C6 C1 1.407(2)
C7 C8 1.402(2)
C1 C2 1.387(2)
N2 C13 1.287(2)
N2 N3 1.411(2)
C11 H11 0.9300
C9 C8 1.383(2)
C9 H9 0.9300
C5 C4 1.388(3)
C5 H5 0.9300
C15 C16 1.512(3)
C15 H15A 0.9700
C15 H15B 0.9700
N3 C14 1.282(2)
C8 H8 0.9300
C2 C3 1.379(3)
C2 H2 0.9300
C14 C17 1.480(2)
C4 C3 1.380(3)
C4 H4 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C3 H3 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657515
