Crystal structures and Hirshfeld surface analysis of 5-amino-1-(4-methoxyphenyl)pyrazole-4-carboxylic acid and 5-amino-3-(4-methoxyphenyl)isoxazole
Pintro, Chirs J.; Long, Analeece K.; Amonette, Allison J.; Lobue, James M.; Padgett, Clifford W.; Acta Crystallographica Section E 78 (2022) 336–339; doi:10.1107/S2056989022001827

data_2244042
_publ_section_title
;
 Crystal structures and Hirshfeld surface analysis of
 5-amino-1-(4-methoxyphenyl)pyrazole-4-carboxylic acid and
 5-amino-3-(4-methoxyphenyl)isoxazole
;
_journal_coeditor_code           HB8013
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              336
_journal_page_last               339
_journal_paper_doi               10.1107/S2056989022001827
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C10 H10 N2 O2'
_chemical_formula_moiety         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20
_chemical_name_systematic
;
5-Amino-3-(4-methoxyphenyl)isoxazole
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6496(11)
_cell_length_b                   8.7565(15)
_cell_length_c                   14.128(2)
_cell_measurement_reflns_used    1405
_cell_measurement_temperature    170
_cell_measurement_theta_max      22.5120
_cell_measurement_theta_min      2.6640
_cell_volume                     946.3(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i>  (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/1</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      170
_diffrn_detector                 'Rigaku XtaLAB area detector'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.163
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 385 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       0.037(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/1 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0606P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                1344
_reflns_number_total             2635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8013sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        946.4(3)
_cod_database_code               2244042
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              13666
_shelx_res_checksum              96743
_cod_database_fobs_code 2244042