Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-<i>X</i>C~6~H~3~C=NOH (<i>X</i> = H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns
Gomes, Ligia R.; de Souza, Marcus V. N.; Da Costa, Cristiane F.; Wardell, James L.; Low, John Nicolson; Acta Crystallographica Section E 74 (2018) 1553–1560; doi:10.1107/S2056989018014020

data_2242667
_publ_section_title
;
 Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde
 oxime derivatives, 2-MeO-<i>X</i>C~6~H~3~C=NOH (<i>X</i> = H and 2-, 3-
 and 4-MeO): different conformations and hydrogen-bonding patterns
;
_journal_coeditor_code           QM2129
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1553
_journal_page_last               1560
_journal_paper_doi               10.1107/S2056989018014020
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H11 N O3'
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_name_systematic        '2,3-Dimethoxy-benzaldehyde oxime'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6775(2)
_cell_length_b                   13.0996(5)
_cell_length_c                   14.1984(5)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.4600
_cell_measurement_theta_min      4.6110
_cell_volume                     869.98(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2006)
;
_computing_publication_material
;
OSCAIL (McArdle <i>et al.</i>,  2004),
SHELXL (Sheldrick, 2015b) and
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
OSCAIL (McArdle <i>et al.</i>,  2004),
<i>ShelXle</i> (H\"ubschle <i>et al.</i>,  2011) and
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
OSCAIL (McArdle <i>et al.</i>,  2004) and
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
;
Rigaku 007HF equipped with Varimax confocal mirrors and an
AFC11 goniometer and HyPix 6000 detector
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7835
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         4.593
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 474 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1064P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                1371
_reflns_number_total             1596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qm2129sup1.cif
_cod_data_source_block           2
_cod_database_code               2242667
_cod_database_fobs_code          2242667
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.983
_shelx_hkl_checksum              37344
_shelx_res_checksum              3481