#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201982.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_2201982
loop_
_publ_author_name
'Luck, Rudy L.'
'Li, Kexue'
'Bates, Dallas K.'
_publ_section_title
;6-Methyl-11a,12-dihydro-6H-quino[3,2-b][1,4]benzothiazine:
 an amidine formed under unusual conditions
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o302
_journal_page_last               o303
_journal_paper_doi               10.1107/S1600536803002988
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H14 N2 S1'
_chemical_formula_moiety         'C16 H14 N2 S1'
_chemical_formula_sum            'C16 H14 N2 S'
_chemical_formula_weight         266.35
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.775(4)
_cell_length_b                   5.3810(10)
_cell_length_c                   10.587(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      10
_cell_volume                     1297.5(4)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method       'non-profiled ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1274
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1214
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0457P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                844
_reflns_number_total             1214
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6017.cif
_cod_data_source_block           4
_cod_database_code               2201982
_cod_database_fobs_code          2201982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
loop_
_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
_atom_site_type_symbol
C1 0.44282(18) 0.5428(9) 0.4459(5) 0.0481(12) Uani d . 1 . . C
C2 0.4880(2) 0.5195(11) 0.3583(6) 0.0621(14) Uani d . 1 . . C
H2 0.4872 0.3901 0.3001 0.075 Uiso calc R 1 . . H
C3 0.5338(2) 0.6865(11) 0.3570(5) 0.0651(15) Uani d . 1 . . C
H3 0.5632 0.6733 0.2964 0.078 Uiso calc R 1 . . H
C4 0.5358(2) 0.8722(10) 0.4454(6) 0.0663(15) Uani d . 1 . . C
H4 0.5668 0.9848 0.4446 0.08 Uiso calc R 1 . . H
C5 0.49222(17) 0.8941(8) 0.5358(6) 0.0561(13) Uani d . 1 . . C
H5 0.4945 1.0178 0.597 0.067 Uiso calc R 1 . . H
C6 0.44493(16) 0.7300(8) 0.5349(5) 0.0464(11) Uani d . 1 . . C
C7 0.35008(18) 0.6674(8) 0.6054(5) 0.0424(11) Uani d . 1 . . C
C8 0.33665(18) 0.5082(9) 0.4924(4) 0.0466(12) Uani d . 1 . . C
H8 0.3233 0.6156 0.4234 0.056 Uiso calc R 1 . . H
C9 0.39129(18) 0.3705(10) 0.4496(6) 0.0620(14) Uani d . 1 . . C
H9A 0.3993 0.2346 0.5073 0.074 Uiso calc R 1 . . H
H9B 0.3848 0.3009 0.3662 0.074 Uiso calc R 1 . . H
C10 0.3196(2) 0.8677(12) 0.7997(5) 0.0667(16) Uani d . 1 . . C
H10A 0.2856 0.8877 0.8521 0.1 Uiso calc R 1 . . H
H10B 0.333 1.0277 0.7716 0.1 Uiso calc R 1 . . H
H10C 0.3502 0.7881 0.8473 0.1 Uiso calc R 1 . . H
C11 0.2448(2) 0.6820(8) 0.6598(4) 0.0447(11) Uani d . 1 . . C
C12 0.20197(19) 0.8427(10) 0.7052(5) 0.0514(12) Uani d . 1 . . C
H12 0.213 0.9802 0.7528 0.062 Uiso calc R 1 . . H
C13 0.1426(2) 0.8009(10) 0.6803(5) 0.0601(14) Uani d . 1 . . C
H13 0.1145 0.9095 0.7118 0.072 Uiso calc R 1 . . H
C14 0.1258(2) 0.5990(10) 0.6092(6) 0.0608(15) Uani d . 1 . . C
H14 0.0862 0.5683 0.5939 0.073 Uiso calc R 1 . . H
C15 0.16821(19) 0.4428(10) 0.5609(5) 0.0589(15) Uani d . 1 . . C
H15 0.1571 0.3084 0.5111 0.071 Uiso calc R 1 . . H
C16 0.22696(17) 0.4831(8) 0.5854(5) 0.0483(12) Uani d . 1 . . C
N1 0.40020(14) 0.7687(7) 0.6254(4) 0.0468(10) Uani d . 1 . . N
N2 0.30480(15) 0.7159(7) 0.6911(4) 0.0459(10) Uani d . 1 . . N
S1 0.28038(5) 0.2798(2) 0.52419(16) 0.0649(5) Uani d . 1 . . S
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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 6 4
1 1 11
2 1 8
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 119.7(4)
C6 C1 C9 117.5(4)
C2 C1 C9 122.8(5)
C3 C2 C1 120.6(5)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 119.6(5)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 120.7(5)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 119.7(5)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 119.6(5)
C1 C6 N1 123.0(4)
C5 C6 N1 117.3(5)
N1 C7 N2 118.0(4)
N1 C7 C8 123.7(4)
N2 C7 C8 118.2(4)
C7 C8 C9 110.4(4)
C7 C8 S1 112.6(3)
C9 C8 S1 107.8(3)
C7 C8 H8 108.7
C9 C8 H8 108.7
S1 C8 H8 108.7
C1 C9 C8 110.4(4)
C1 C9 H9A 109.6
C8 C9 H9A 109.6
C1 C9 H9B 109.6
C8 C9 H9B 109.6
H9A C9 H9B 108.1
N2 C10 H10A 109.5
N2 C10 H10B 109.5
H10A C10 H10B 109.5
N2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 118.0(4)
C16 C11 N2 120.9(4)
C12 C11 N2 121.1(4)
C11 C12 C13 121.0(5)
C11 C12 H12 119.5
C13 C12 H12 119.5
C14 C13 C12 120.0(5)
C14 C13 H13 120
C12 C13 H13 120
C13 C14 C15 119.3(5)
C13 C14 H14 120.4
C15 C14 H14 120.4
C14 C15 C16 120.9(5)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C11 120.8(4)
C15 C16 S1 120.2(4)
C11 C16 S1 119.0(3)
C7 N1 C6 117.8(4)
C7 N2 C11 122.3(4)
C7 N2 C10 116.6(3)
C11 N2 C10 118.8(4)
C16 S1 C8 97.8(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
C1 C6 . 1.381(6) ?
C1 C2 . 1.391(7) ?
C1 C9 . 1.496(6) ?
C2 C3 . 1.377(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.370(8) ?
C3 H3 . 0.93 ?
C4 C5 . 1.384(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.393(5) ?
C5 H5 . 0.93 ?
C6 N1 . 1.414(5) ?
C7 N1 . 1.283(5) ?
C7 N2 . 1.399(6) ?
C7 C8 . 1.503(6) ?
C8 C9 . 1.517(6) ?
C8 S1 . 1.807(4) ?
C8 H8 . 0.98 ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 N2 . 1.450(6) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 C16 . 1.390(6) ?
C11 C12 . 1.390(7) ?
C11 N2 . 1.417(6) ?
C12 C13 . 1.395(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.376(7) ?
C13 H13 . 0.93 ?
C14 C15 . 1.379(7) ?
C14 H14 . 0.93 ?
C15 C16 . 1.380(5) ?
C15 H15 . 0.93 ?
C16 S1 . 1.760(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9240535
