3-[(Benzo-1,3-dioxol-5-yl)amino]-4-methoxycyclobut-3-ene-1,2-dione: polymorphism and twinning of a precursor to an antimycobacterial squaramide.
Palme, Paul R.; Goddard, Richard; Richter, Adrian; Imming, Peter; Seidel, Rüdiger W; Acta crystallographica. Section C, Structural chemistry 80 (2024) –; doi:10.1107/S2053229624006211

data_2312546
_publ_section_title
;
 3-[(Benzo-1,3-dioxol-5-yl)amino]-4-methoxycyclobut-3-ene-1,2-dione:
 polymorphism and twinning of a precursor to an antimycobacterial
 squaramide.
;
_journal_coeditor_code           VP3038
_journal_issue                   8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624006211
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H9 N O5'
_chemical_formula_moiety         'C12 H9 N O5'
_chemical_formula_sum            'C12 H9 N O5'
_chemical_formula_weight         247.20
_chemical_name_systematic
;
3-[(Benzo-1,3-dioxol-5-yl)amino]-4-methoxycyclobut-3-ene-1,2-dione
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                89.550(8)
_cell_angle_beta                 86.967(6)
_cell_angle_gamma                81.460(6)
_cell_formula_units_Z            4
_cell_length_a                   3.7001(4)
_cell_length_b                   12.4583(15)
_cell_length_c                   22.846(3)
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.43
_cell_volume                     1040.0(2)
_computing_cell_refinement
;
SAINT (Bruker, 2019)
;
_computing_data_collection
;
APEX5 (Bruker, 2022)
;
_computing_data_reduction
;
SAINT (Bruker, 2019)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018) and Mercury (Macrae <i>et al.</i>,
2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            76269
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.99782
_exptl_absorpt_correction_T_min  0.99135
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.355
_refine_ls_extinction_coef       0.042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019 (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0992P)^2^+0.1380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                3902
_reflns_number_total             5138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vp3038.cif
_cod_data_source_block           3-II
_cod_database_code               2312546
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.996
_shelx_hkl_checksum              67787
_shelx_res_checksum              86683