Fungal Biotransformation of Tetracycline Antibiotics.
Shang, Zhuo; Salim, Angela A.; Khalil, Zeinab; Bernhardt, Paul V.; Capon, Robert J.; The Journal of organic chemistry 81 (2016) 6186–6194; doi:10.1021/acs.joc.6b01272

data_4037021
_publ_section_title
;
 Fungal Biotransformation of Tetracycline Antibiotics.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6186
_journal_page_last               6194
_journal_paper_doi               10.1021/acs.joc.6b01272
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H18 N2 O7, H2O'
_chemical_formula_sum            'C19 H20 N2 O8'
_chemical_formula_weight         404.37
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_date             2016-05-17T13:46:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.691(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1814(3)
_cell_length_b                   6.3315(3)
_cell_length_c                   16.7915(11)
_cell_measurement_reflns_used    3610
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      62.681
_cell_measurement_theta_min      5.248
_cell_measurement_wavelength     1.54184
_cell_volume                     868.85(8)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0131854
_diffrn_orient_matrix_UB_12      0.0734217
_diffrn_orient_matrix_UB_13      -0.086892
_diffrn_orient_matrix_UB_21      0.110978
_diffrn_orient_matrix_UB_22      0.1842381
_diffrn_orient_matrix_UB_23      0.0286125
_diffrn_orient_matrix_UB_31      0.1518762
_diffrn_orient_matrix_UB_32      -0.1409615
_diffrn_orient_matrix_UB_33      -0.0079194
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4657
_diffrn_reflns_theta_full        62.48
_diffrn_reflns_theta_max         62.48
_diffrn_reflns_theta_min         5.27
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.59486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.8192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                1775
_reflns_number_total             1848
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo6b01272_si_002.cif
_cod_data_source_block           1260rc3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037021