Crystallographic characterization of the first reported crystalline form of the potent hallucinogen (<i>R</i>)-2-amino-1-(8-bromobenzo[1,2-<i>b</i>;5,4-<i>b</i>']difuran-4-yl)propane or `bromodragonfly': the 1:1 anhydrous proton-transfer compound with 3,5-dinitrosalicylic acid
Smith, Graham; Cotton, Marcus S.; Wermuth, Urs D.; Boyd, Sue E.; Acta Crystallographica Section C 66 (2010) o252–o255; doi:10.1107/S0108270110012850

data_2017649
_publ_section_title
;
 Crystallographic characterization of the first reported crystalline
 form of the potent hallucinogen
 (<i>R</i>)-2-amino-1-(8-bromobenzo[1,2-<i>b</i>;5,4-<i>b</i>']difuran-4-yl)propane
 or `bromodragonfly': the 1:1 anhydrous proton-transfer compound with
 3,5-dinitrosalicylic acid
;
_journal_coeditor_code           GA3145
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o252
_journal_page_last               o255
_journal_paper_doi               10.1107/S0108270110012850
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H13 Br N O2 + , C7 H3 N2 O7 -'
_chemical_formula_moiety         'C13 H13 Br N O2 + , C7 H3 N2 O7 -'
_chemical_formula_sum            'C20 H16 Br N3 O9'
_chemical_formula_weight         522.28
_chemical_melting_point_gt       493
_chemical_melting_point_lt       495
_chemical_name_common            'bromodragonfly 3,5-dinitrosalicylate'
_chemical_name_systematic
;
1-(8-bromobenzo[1,2-<i>b</i>;5,4-<i>b</i>']difuran-4-yl)propan-2-aminium
2-carboxy-4,6-dinitrophenolate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.315(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9596(3)
_cell_length_b                   17.2201(9)
_cell_length_c                   8.7147(4)
_cell_measurement_reflns_used    5783
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32.59
_cell_measurement_theta_min      3.02
_cell_volume                     1016.34(8)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Oxford Gemini-S Ultra CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10418
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  0.590
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details 'Flack (1983), with 2047 Friedel pairs'
_refine_ls_abs_structure_Flack   0.038(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0730P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3733
_reflns_number_total             4450
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga3145.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017649
_cod_database_fobs_code          2017649