Redetermination of rifampicin pentahydrate revealing a zwitterionic form of the antibiotic
Wicher, Barbara; Pyta, Krystian; Przybylski, Piotr; Tykarska, Ewa; Gdaniec, Maria; Acta Crystallographica Section C 68 (2012) o209–o212; doi:10.1107/S0108270112015296

data_2018475
_publ_section_title
;
 Redetermination of rifampicin pentahydrate revealing a zwitterionic form
 of the antibiotic
;
_journal_coeditor_code           FA3275
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o209
_journal_page_last               o212
_journal_paper_doi               10.1107/S0108270112015296
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C43 H58 N4 O12 , 5H2 O'
_chemical_formula_moiety         'C43 H58 N4 O12, 5(H2 O)'
_chemical_formula_sum            'C43 H68 N4 O17'
_chemical_formula_weight         913.01
_chemical_name_common            'rifampicin pentahydrate'
_chemical_name_systematic
;
(2<i>S</i>,12<i>Z</i>,14<i>E</i>,16<i>S</i>,17<i>S</i>,18<i>R</i>,
19<i>R</i>,20<i>R</i>,21<i>S</i>,22<i>R</i>,23<i>S</i>,24<i>E</i>)-21-
acetyloxy-6,9,17,19-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-
8-[(<i>E</i>)-<i>N</i>-(4-methylpiperazin-4-ium-1-yl)formimidoyl]-1,11-dioxo-
1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-<i>b</i>]furan-
5-olate pentahydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8506(6)
_cell_length_b                   17.3867(8)
_cell_length_c                   19.7476(8)
_cell_measurement_reflns_used    5773
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.58
_cell_measurement_theta_min      2.54
_cell_volume                     4755.5(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla <i>et al.</i>, 2005)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova Cu X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13055
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         6.39
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.493
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         4805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0916P)^2^+1.4280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                4531
_reflns_number_total             4805
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3275.cif
_cod_data_source_block           I
_cod_database_code               2018475
_cod_database_fobs_code          2018475