##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2021-06-21
_journal_date_accepted     2021-06-28
_journal_name_full     'IUCrData'
_journal_year     2021
_journal_volume     6
_journal_issue      6
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431462100674X
_journal_coeditor_code     XU4044
_publ_contact_author_name     'Akoun Abou'
_publ_contact_author_address
;
Department of Training and Research in Electrical and Electronic Engineering,
Research Team: Instrumentation, Image and Spectroscopy,
Félix Houphouët-Boigny National Polytechnic Institute, BP 1093 Yamoussoukro,
Côte d'Ivoire
;
_publ_contact_author_email     'abouakoun@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+2250709800015'
_publ_section_title
;
8-Methyl-3-methylsulfanyl-8a,8
b-dihydro-5H-1-oxa-2,4-diazaacenaphthylene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Abou, Akoun' .
;
Department of Training and Research in Electrical and Electronic Engineering,
Research Team: Instrumentation, Image and Spectroscopy,
Félix Houphouët-Boigny National Polytechnic Institute,
BP 1093 Yamoussoukro, Côte d'Ivoire
;
    'Bamba, Fanté' .
;
Laboratoire de Constitution et Réaction de la Matière, UFR SSMT,
Université Félix Houphouët-Boigny, 22 BP 582 Abidjan 22,
Côte d'Ivoire
;
    'Marrot, Jérôme' .
;
Laboratoire ILV-UVSQ-UMR 8180 CNRS, 45 Avenue des Etats Unis,
78035 Versailles Cedex,
France
;
    'Yaya, Soro' .
;
Laboratoire des Procédés Industriels de Synthèse et d'Environnement,
Institut National Polytechnique Félix Houphouët-Boigny,
BP 991 Yamoussoukro, Côte d'Ivoire
;
    'Coustard, Jean-Marie' 'Deceased August 2013.'
;
Laboratoire IC2MP-UMR 7285 CNRS, 40 Avenue du Recteur Pineau,
86022 Poitiers Cedex,
France
;
_publ_section_synopsis
;
In the structure of the diazadihydroacenaphthylene derivative reported here,
stabilization is provided by C---H...N and C---H...π interactions.
;
_chemical_name_systematic
;
8-Methyl-3-methylsulfanyl-8a,8b-dihydro-5H-1-oxa-2,4-diazaacenaphthylene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H12 N2 O S'
_chemical_formula_sum     'C11 H12 N2 O S'
_chemical_formula_iupac     'C11 H12 N2 O S'
_chemical_formula_weight     220.29
_chemical_melting_point     393.1
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     8.0175(2)
_cell_length_b     14.4611(3)
_cell_length_c     18.5612(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2152.02(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8401
_cell_measurement_theta_min     2.19
_cell_measurement_theta_max     29.79
_cell_measurement_temperature     293(2)
_exptl_crystal_description     parallelepiped
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.300
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.360
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     928
_exptl_absorpt_coefficient_mu     0.274
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.9223
_exptl_absorpt_correction_T_max     0.9837
_diffrn_ambient_temperature     293(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker CCD area detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     512
_diffrn_reflns_number     67637
_diffrn_reflns_av_R_equivalents     0.0318
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_theta_min     2.817
_diffrn_reflns_theta_max     30.068
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_refine_special_details     ?
_reflns_number_total     3155
_reflns_number_gt     2560
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0534
_refine_ls_R_factor_gt     0.0414
_refine_ls_wR_factor_gt     0.1130
_refine_ls_wR_factor_ref     0.1293
_refine_ls_goodness_of_fit_ref     1.081
_refine_ls_restrained_S_all     1.081
_refine_ls_number_reflns     3155
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0606P)²+0.5724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.321
_refine_diff_density_min     -0.192
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SIR2019 (Burla et al., 2015)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020), WinGX (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015) and publCIF (Westrip,
2010)
;
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 S1 0.87930(6) 0.23268(3) 0.81332(2) 0.05945(15) Uani d 1 . .
    C C1 0.68279(16) 0.11024(8) 0.99475(8) 0.0430(3) Uani d 1 . .
    H H1 0.567035 0.131511 0.991152 0.052 Uiso calc 1 . .
    C C2 0.79398(16) 0.16562(8) 0.94630(7) 0.0411(3) Uani d 1 . .
    C C3 0.78747(16) 0.14749(9) 0.86830(8) 0.0441(3) Uani d 1 . .
    N N4 0.72257(16) 0.07471(9) 0.84198(7) 0.0527(3) Uani d 1 . .
    C C5 0.6511(2) 0.00367(11) 0.89045(9) 0.0581(4) Uani d 1 . .
    H H5A 0.685682 -0.056803 0.873466 0.070 Uiso calc 1 . .
    H H5B 0.530492 0.006443 0.887046 0.070 Uiso calc 1 . .
    C C6 0.69925(16) 0.01268(9) 0.96758(8) 0.0458(3) Uani d 1 . .
    C C7 0.77226(18) -0.05134(9) 1.00803(9) 0.0512(3) Uani d 1 . .
    H H7 0.786148 -0.110657 0.989631 0.061 Uiso calc 1 . .
    C C8 0.8308(2) -0.03094(10) 1.08014(9) 0.0543(4) Uani d 1 . .
    H H8 0.871921 -0.079538 1.107742 0.065 Uiso calc 1 . .
    C C9 0.8293(2) 0.05336(11) 1.10934(9) 0.0544(3) Uani d 1 . .
    C C10 0.7554(2) 0.13333(9) 1.06827(8) 0.0492(3) Uani d 1 . .
    H H10 0.668392 0.162125 1.097811 0.059 Uiso calc 1 . .
    O O11 0.88721(16) 0.20355(7) 1.05266(6) 0.0584(3) Uani d 1 . .
    N N12 0.90369(16) 0.21466(8) 0.97783(7) 0.0486(3) Uani d 1 . .
    C C13 0.8627(3) 0.17816(14) 0.72661(9) 0.0685(5) Uani d 1 . .
    H H13A 0.748115 0.177828 0.711577 0.103 Uiso calc 1 . .
    H H13B 0.902781 0.115738 0.729744 0.103 Uiso calc 1 . .
    H H13C 0.928286 0.211794 0.692175 0.103 Uiso calc 1 . .
    C C14 0.8944(4) 0.07297(16) 1.18338(10) 0.0846(7) Uani d 1 . .
    H H14A 0.928090 0.016115 1.205768 0.127 Uiso calc 1 . .
    H H14B 0.808424 0.101512 1.211680 0.127 Uiso calc 1 . .
    H H14C 0.988454 0.113844 1.180153 0.127 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 . 1.7610(14) ?
    S1 C13 . 1.7972(18) ?
    C1 C2 . 1.4984(18) ?
    C1 C6 . 1.5039(17) ?
    C1 C10 . 1.521(2) ?
    C1 H1 . 0.9800 ?
    C2 N12 . 1.2724(17) ?
    C2 C3 . 1.4723(19) ?
    C3 N4 . 1.2717(17) ?
    N4 C5 . 1.481(2) ?
    C5 C6 . 1.489(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.328(2) ?
    C7 C8 . 1.449(2) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.334(2) ?
    C8 H8 . 0.9300 ?
    C9 C14 . 1.497(3) ?
    C9 C10 . 1.506(2) ?
    C10 O11 . 1.4942(18) ?
    C10 H10 . 0.9800 ?
    O11 N12 . 1.4045(16) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
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
    C3 S1 C13 . . 100.43(8) ?
    C2 C1 C6 . . 104.35(10) ?
    C2 C1 C10 . . 101.16(11) ?
    C6 C1 C10 . . 118.25(12) ?
    C2 C1 H1 . . 110.8 ?
    C6 C1 H1 . . 110.8 ?
    C10 C1 H1 . . 110.8 ?
    N12 C2 C3 . . 125.17(12) ?
    N12 C2 C1 . . 115.67(12) ?
    C3 C2 C1 . . 118.29(11) ?
    N4 C3 C2 . . 122.66(13) ?
    N4 C3 S1 . . 121.83(12) ?
    C2 C3 S1 . . 115.49(9) ?
    C3 N4 C5 . . 119.94(13) ?
    N4 C5 C6 . . 115.04(12) ?
    N4 C5 H5A . . 108.5 ?
    C6 C5 H5A . . 108.5 ?
    N4 C5 H5B . . 108.5 ?
    C6 C5 H5B . . 108.5 ?
    H5A C5 H5B . . 107.5 ?
    C7 C6 C5 . . 126.65(14) ?
    C7 C6 C1 . . 120.20(14) ?
    C5 C6 C1 . . 112.45(13) ?
    C6 C7 C8 . . 121.55(13) ?
    C6 C7 H7 . . 119.2 ?
    C8 C7 H7 . . 119.2 ?
    C9 C8 C7 . . 123.94(14) ?
    C9 C8 H8 . . 118.0 ?
    C7 C8 H8 . . 118.0 ?
    C8 C9 C14 . . 122.87(16) ?
    C8 C9 C10 . . 119.97(15) ?
    C14 C9 C10 . . 117.15(15) ?
    O11 C10 C9 . . 109.97(13) ?
    O11 C10 C1 . . 104.24(10) ?
    C9 C10 C1 . . 115.85(12) ?
    O11 C10 H10 . . 108.8 ?
    C9 C10 H10 . . 108.8 ?
    C1 C10 H10 . . 108.8 ?
    N12 O11 C10 . . 109.64(10) ?
    C2 N12 O11 . . 109.03(11) ?
    S1 C13 H13A . . 109.5 ?
    S1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    S1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C9 C14 H14A . . 109.5 ?
    C9 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C9 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
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
    C1 H1 N12 4_457 0.98 2.64 3.4173(16) 135.9 yes
    C5 H5B Cg3 5_565 0.97 2.80 3.6158(17) 142 yes
_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     0.922
_shelx_estimated_absorpt_T_max     0.984
