Extensive hydrogen and halogen bonding, and absence of intramolecular hydrogen bonding between alcohol and nitro groups in a series of <i>endo</i>-nitronorbornanol compounds
Lemmerer, Andreas; Michael, Joseph P.; Acta Crystallographica Section C 67 (2011) o288–o293; doi:10.1107/S0108270111024140

data_2018183
_publ_section_title
;
 Extensive hydrogen and halogen bonding, and absence of intramolecular
 hydrogen bonding between alcohol and nitro groups in a series of
 <i>endo</i>-nitronorbornanol compounds
;
_journal_coeditor_code           GD3390
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o288
_journal_page_last               o293
_journal_paper_doi               10.1107/S0108270111024140
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H19 Br2 N O5'
_chemical_formula_moiety         'C22 H19 Br2 N O5'
_chemical_formula_sum            'C22 H19 Br2 N O5'
_chemical_formula_weight         537.2
_chemical_name_systematic
;
(+-)-methyl
3-<i>exo</i>,6-<i>exo</i>-dibromo-7-(diphenylmethylidene)-5-<i>endo</i>-
hydroxy-3-<i>endo</i>-nitrobicyclo[2.2.1]heptane-2-<i>exo</i>-carboxylate
;
_space_group_IT_number           14
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_cell_angle_beta                 98.219(2)
_cell_angle_gamma                90
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_cell_length_b                   9.0341(4)
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_cell_measurement_reflns_used    3493
_cell_measurement_temperature    173(2)
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_cell_measurement_theta_min      2.59
_cell_volume                     2129.71(17)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
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_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
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_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
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_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
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_exptl_crystal_colour            brown
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
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_exptl_crystal_size_min          0.06
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_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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_cod_database_fobs_code          2018183