Solid state chemistry of the antibiotic doxycycline: structure of the neutral monohydrate and insights into its poor water solubility
Legendre, Alexandre O.; Silva, Laila R. R.; Silva, Douglas M.; Rosa, Iara M. L.; Azarias, Lilian C.; de Abreu, Polyana J.; de Araújo, Magali B.; Neves, Person P.; Torres, Claudia; Martins, Felipe T.; Doriguetto, Antonio C.; CrystEngComm 14 (2012) 2532–; doi:10.1039/c1ce06181j

data_7207515
_publ_section_title
;
 Solid state chemistry of the antibiotic doxycycline: structure of the
 neutral monohydrate and insights into its poor water solubility
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2532
_journal_paper_doi               10.1039/c1ce06181j
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_moiety
;
C22 H24 N2 O8, H2 O
;
_chemical_formula_sum            'C22 H26 N2 O9'
_chemical_formula_weight         462.45
_chemical_name_common            'doxycycline monohydrate'
_chemical_name_systematic
;
6-Deoxy-5-oxytetracycline monohydrate
;
_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_date             2011-02-13T10:17:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.192(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.9241(1)
_cell_length_b                   9.4808(2)
_cell_length_c                   18.5568(4)
_cell_measurement_reflns_used    7685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.7636
_cell_measurement_theta_min      3.0661
_cell_volume                     1042.02(4)
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16517
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.84
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.0142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3492
_reflns_number_total             3786
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ce06181j.txt
_cod_data_source_block           doxi_100
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7207515