##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2023-04-17
_journal_date_accepted     2023-05-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      6
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023004139
_journal_coeditor_code     HB8064
_publ_contact_author_name     'Aravazhi Amalan Thiruvalluvar'
_publ_contact_author_address
;
Principal (Retired)
Kunthavai Naacchiyaar Government Arts College for Women (Autonomous)
Thanjavur 613 007
Tamilnadu
India
;
_publ_contact_author_email     'thiruvalluvar.a@gmail.com'
_publ_contact_author_fax     'None'
_publ_contact_author_phone     '+919894889103'
_publ_section_title
;
Synthesis, crystal structure and Hirshfeld surface analysis of
(E)-benzo[d][1,3]dioxole-5-carbaldehyde oxime
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Radhakrishnan, Rengaraj' .
;
P. G. & Research Department of Physics
Jamal Mohamed College (Autonomous)
(affiliated to Bharathidasan University)
Tiruchirappalli 620 020
Tamilnadu
India
;
    'Mustaphi, Nour El Hoda' .
;
Laboratoire Chimie Organique Catalyse et Environnement
Faculté des Sciences
Kenitra
Morocco
;
    'Sebbar, Nada Kheira' .
;
Laboratory of Chemistry and Environment
Applied Bioorganic Chemistry Team
Faculty of Sciences
Ibn Zohr University
Agadir
Morocco
;
    'Mague, Joel T.' .
;
Department of Chemistry
Tulane University
New Orleans
LA 70118
USA
;
    'Thiruvalluvar, Aravazhi Amalan' .
;
Principal (Retired)
Kunthavai Naacchiyaar Government Arts College for Women (Autonomous)
Thanjavur 613 007
Tamilnadu
India
;
_publ_section_synopsis
;
The asymmetric unit of the title compound consists of two independent molecules
differing slightly in conformation and in their intermolecular interactions in
the solid.
;
_chemical_name_systematic
;
(E)-Benzo[d][1,3]dioxole-5-carbaldehyde oxime
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H7 N O3'
_chemical_formula_sum     'C8 H7 N O3'
_chemical_formula_iupac     'C8 H7 N O3'
_chemical_formula_weight     165.15
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     6.8724(14)
_cell_length_b     33.502(7)
_cell_length_c     7.3449(15)
_cell_angle_alpha     90
_cell_angle_beta     117.238(3)
_cell_angle_gamma     90
_cell_volume     1503.6(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6661
_cell_measurement_theta_min     2.432
_cell_measurement_theta_max     28.126
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.355
_exptl_crystal_size_mid     0.166
_exptl_crystal_size_min     0.097
_exptl_crystal_density_diffrn     1.459
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.114
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min     0.82
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, collected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;
_diffrn_ambient_temperature     150(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 SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     28032
_diffrn_reflns_av_R_equivalents     0.0479
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_theta_min     2.432
_diffrn_reflns_theta_max     28.677
_diffrn_reflns_theta_full     28.650
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -45
_diffrn_reflns_limit_k_max     43
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those
attached to oxygen were placed in locations derived from a difference
map and their coordinates adjusted to give O---H = 0.87 Å. All were included
as riding contributions with isotropic displacement parameters 1.2 - 1.5
times those of the attached atoms.
;
_reflns_number_total     3858
_reflns_number_gt     2836
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0659
_refine_ls_R_factor_gt     0.0458
_refine_ls_wR_factor_gt     0.1178
_refine_ls_wR_factor_ref     0.1265
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     3858
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0621P)²+0.2227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.310
_refine_diff_density_min     -0.193
_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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012), PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2020) 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
    O O1 0.21075(18) 0.58110(3) 0.12890(17) 0.0385(3) Uani d 1 . .
    O O2 0.50131(18) 0.54433(3) 0.13879(17) 0.0377(3) Uani d 1 . .
    O O3 0.40957(17) 0.36128(3) 0.45505(17) 0.0377(3) Uani d 1 . .
    H H3A 0.516808 0.349351 0.445154 0.057 Uiso d 1 . .
    N N1 0.43129(18) 0.40031(3) 0.39281(18) 0.0287(3) Uani d 1 . .
    C C1 0.2551(2) 0.46413(4) 0.30915(19) 0.0254(3) Uani d 1 . .
    C C2 0.0814(2) 0.48668(4) 0.3030(2) 0.0290(3) Uani d 1 . .
    H H2 -0.020388 0.474321 0.339202 0.035 Uiso calc 1 . .
    C C3 0.0524(2) 0.52685(4) 0.2452(2) 0.0316(3) Uani d 1 . .
    H H3 -0.065828 0.542093 0.241589 0.038 Uiso calc 1 . .
    C C4 0.2043(2) 0.54306(4) 0.1939(2) 0.0280(3) Uani d 1 . .
    C C5 0.3775(2) 0.52084(4) 0.1994(2) 0.0262(3) Uani d 1 . .
    C C6 0.4081(2) 0.48172(4) 0.25517(19) 0.0252(3) Uani d 1 . .
    H H6 0.527136 0.466906 0.257669 0.030 Uiso calc 1 . .
    C C7 0.4031(3) 0.58311(4) 0.0990(3) 0.0379(4) Uani d 1 . .
    H H7A 0.363159 0.591287 -0.043339 0.045 Uiso calc 1 . .
    H H7B 0.507199 0.602939 0.193416 0.045 Uiso calc 1 . .
    C C8 0.2711(2) 0.42252(4) 0.3722(2) 0.0285(3) Uani d 1 . .
    H H8 0.159251 0.411565 0.398925 0.034 Uiso calc 1 . .
    O O4 0.79029(19) 0.15551(3) 0.4126(2) 0.0489(3) Uani d 1 . .
    O O5 0.54405(19) 0.19665(3) 0.4559(2) 0.0488(3) Uani d 1 . .
    O O6 0.84324(18) 0.38394(3) 0.42029(17) 0.0392(3) Uani d 1 . .
    H H6A 0.725059 0.395443 0.409864 0.059 Uiso d 1 . .
    N N2 0.78297(19) 0.34360(4) 0.42083(18) 0.0299(3) Uani d 1 . .
    C C9 0.8894(2) 0.27623(4) 0.4103(2) 0.0266(3) Uani d 1 . .
    C C10 1.0360(2) 0.25112(4) 0.3838(2) 0.0319(3) Uani d 1 . .
    H H10 1.152810 0.262583 0.366388 0.038 Uiso calc 1 . .
    C C11 1.0166(2) 0.20967(5) 0.3820(2) 0.0354(3) Uani d 1 . .
    H H11 1.116764 0.192674 0.363450 0.043 Uiso calc 1 . .
    C C12 0.8452(2) 0.19468(4) 0.4082(2) 0.0320(3) Uani d 1 . .
    C C13 0.6986(2) 0.21941(4) 0.4347(2) 0.0302(3) Uani d 1 . .
    C C14 0.7148(2) 0.25990(4) 0.4373(2) 0.0292(3) Uani d 1 . .
    H H14 0.613289 0.276437 0.456418 0.035 Uiso calc 1 . .
    C C15 0.5989(3) 0.15609(4) 0.4420(2) 0.0369(3) Uani d 1 . .
    H H15A 0.476274 0.142790 0.325521 0.044 Uiso calc 1 . .
    H H15B 0.626735 0.141616 0.569104 0.044 Uiso calc 1 . .
    C C16 0.9197(2) 0.31931(4) 0.4083(2) 0.0299(3) Uani d 1 . .
    H H16 1.043047 0.329466 0.397484 0.036 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
    O1 C4 . 1.3685(17) ?
    O1 C7 . 1.4377(19) ?
    O2 C5 . 1.3742(16) ?
    O2 C7 . 1.4311(17) ?
    O3 N1 . 1.4154(15) ?
    O3 H3A . 0.8702 ?
    N1 C8 . 1.2790(18) ?
    C1 C2 . 1.3957(18) ?
    C1 C6 . 1.4110(18) ?
    C1 C8 . 1.4570(19) ?
    C2 C3 . 1.398(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.373(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.3890(19) ?
    C5 C6 . 1.3603(19) ?
    C6 H6 . 0.9500 ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8 . 0.9500 ?
    O4 C12 . 1.3699(18) ?
    O4 C15 . 1.427(2) ?
    O5 C13 . 1.3730(17) ?
    O5 C15 . 1.4264(18) ?
    O6 N2 . 1.4140(15) ?
    O6 H6A . 0.8701 ?
    N2 C16 . 1.2776(18) ?
    C9 C10 . 1.3931(19) ?
    C9 C14 . 1.4129(18) ?
    C9 C16 . 1.4595(19) ?
    C10 C11 . 1.394(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.373(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.3849(19) ?
    C13 C14 . 1.3606(19) ?
    C14 H14 . 0.9500 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 H16 . 0.9500 ?
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
    C4 O1 C7 . . 106.02(11) ?
    C5 O2 C7 . . 106.39(11) ?
    N1 O3 H3A . . 100.3 ?
    C8 N1 O3 . . 111.31(11) ?
    C2 C1 C6 . . 120.04(13) ?
    C2 C1 C8 . . 117.85(12) ?
    C6 C1 C8 . . 122.10(12) ?
    C1 C2 C3 . . 122.15(13) ?
    C1 C2 H2 . . 118.9 ?
    C3 C2 H2 . . 118.9 ?
    C4 C3 C2 . . 116.33(12) ?
    C4 C3 H3 . . 121.8 ?
    C2 C3 H3 . . 121.8 ?
    O1 C4 C3 . . 127.89(13) ?
    O1 C4 C5 . . 110.19(12) ?
    C3 C4 C5 . . 121.91(13) ?
    C6 C5 O2 . . 128.03(12) ?
    C6 C5 C4 . . 122.51(12) ?
    O2 C5 C4 . . 109.45(12) ?
    C5 C6 C1 . . 117.05(12) ?
    C5 C6 H6 . . 121.5 ?
    C1 C6 H6 . . 121.5 ?
    O2 C7 O1 . . 107.86(11) ?
    O2 C7 H7A . . 110.1 ?
    O1 C7 H7A . . 110.1 ?
    O2 C7 H7B . . 110.1 ?
    O1 C7 H7B . . 110.1 ?
    H7A C7 H7B . . 108.4 ?
    N1 C8 C1 . . 122.00(12) ?
    N1 C8 H8 . . 119.0 ?
    C1 C8 H8 . . 119.0 ?
    C12 O4 C15 . . 105.87(11) ?
    C13 O5 C15 . . 106.11(11) ?
    N2 O6 H6A . . 99.2 ?
    C16 N2 O6 . . 112.48(11) ?
    C10 C9 C14 . . 120.06(13) ?
    C10 C9 C16 . . 118.69(12) ?
    C14 C9 C16 . . 121.24(12) ?
    C9 C10 C11 . . 122.04(13) ?
    C9 C10 H10 . . 119.0 ?
    C11 C10 H10 . . 119.0 ?
    C12 C11 C10 . . 116.57(13) ?
    C12 C11 H11 . . 121.7 ?
    C10 C11 H11 . . 121.7 ?
    O4 C12 C11 . . 128.09(13) ?
    O4 C12 C13 . . 110.11(13) ?
    C11 C12 C13 . . 121.80(14) ?
    C14 C13 O5 . . 127.91(12) ?
    C14 C13 C12 . . 122.58(13) ?
    O5 C13 C12 . . 109.51(13) ?
    C13 C14 C9 . . 116.94(12) ?
    C13 C14 H14 . . 121.5 ?
    C9 C14 H14 . . 121.5 ?
    O5 C15 O4 . . 108.40(12) ?
    O5 C15 H15A . . 110.0 ?
    O4 C15 H15A . . 110.0 ?
    O5 C15 H15B . . 110.0 ?
    O4 C15 H15B . . 110.0 ?
    H15A C15 H15B . . 108.4 ?
    N2 C16 C9 . . 121.07(12) ?
    N2 C16 H16 . . 119.5 ?
    C9 C16 H16 . . 119.5 ?
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
    C6 C1 C2 C3 . . . . -0.3(2) ?
    C8 C1 C2 C3 . . . . 179.76(13) ?
    C1 C2 C3 C4 . . . . 0.2(2) ?
    C7 O1 C4 C3 . . . . 179.08(14) ?
    C7 O1 C4 C5 . . . . -2.05(15) ?
    C2 C3 C4 O1 . . . . 178.64(13) ?
    C2 C3 C4 C5 . . . . -0.1(2) ?
    C7 O2 C5 C6 . . . . -179.40(14) ?
    C7 O2 C5 C4 . . . . 1.47(15) ?
    O1 C4 C5 C6 . . . . -178.80(12) ?
    C3 C4 C5 C6 . . . . 0.1(2) ?
    O1 C4 C5 O2 . . . . 0.38(16) ?
    C3 C4 C5 O2 . . . . 179.33(12) ?
    O2 C5 C6 C1 . . . . -179.25(13) ?
    C4 C5 C6 C1 . . . . -0.2(2) ?
    C2 C1 C6 C5 . . . . 0.29(19) ?
    C8 C1 C6 C5 . . . . -179.76(12) ?
    C5 O2 C7 O1 . . . . -2.71(15) ?
    C4 O1 C7 O2 . . . . 2.92(15) ?
    O3 N1 C8 C1 . . . . -179.96(11) ?
    C2 C1 C8 N1 . . . . -176.17(13) ?
    C6 C1 C8 N1 . . . . 3.9(2) ?
    C14 C9 C10 C11 . . . . 0.2(2) ?
    C16 C9 C10 C11 . . . . -179.38(13) ?
    C9 C10 C11 C12 . . . . -0.2(2) ?
    C15 O4 C12 C11 . . . . -179.48(15) ?
    C15 O4 C12 C13 . . . . 0.38(16) ?
    C10 C11 C12 O4 . . . . -179.98(14) ?
    C10 C11 C12 C13 . . . . 0.2(2) ?
    C15 O5 C13 C14 . . . . 179.94(14) ?
    C15 O5 C13 C12 . . . . 0.07(17) ?
    O4 C12 C13 C14 . . . . 179.83(13) ?
    C11 C12 C13 C14 . . . . -0.3(2) ?
    O4 C12 C13 O5 . . . . -0.29(17) ?
    C11 C12 C13 O5 . . . . 179.58(14) ?
    O5 C13 C14 C9 . . . . -179.49(14) ?
    C12 C13 C14 C9 . . . . 0.4(2) ?
    C10 C9 C14 C13 . . . . -0.3(2) ?
    C16 C9 C14 C13 . . . . 179.28(13) ?
    C13 O5 C15 O4 . . . . 0.16(17) ?
    C12 O4 C15 O5 . . . . -0.33(16) ?
    O6 N2 C16 C9 . . . . 178.85(11) ?
    C10 C9 C16 N2 . . . . 176.16(13) ?
    C14 C9 C16 N2 . . . . -3.5(2) ?
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
    O3 H3A N2 . 0.87 1.93 2.7549(16) 158 yes
    C7 H7B O4 2_655 0.99 2.58 3.239(2) 124 yes
    C8 H8 O6 1_455 0.95 2.43 3.3754(18) 173 yes
    O6 H6A N1 . 0.87 1.97 2.7989(17) 158 yes
    C15 H15A O1 2_545 0.99 2.54 3.1775(19) 122 yes
    C16 H16 O3 1_655 0.95 2.59 3.5173(18) 167 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     0.961
_shelx_estimated_absorpt_T_max     0.989
