Alternative solid-state forms of a potent antimalarial aminopyridine: X-ray crystallographic, thermal and solubility aspects
Cruickshank, Dyanne L.; Younis, Yassir; Njuguna, Nicholas M.; Ongarora, Dennis S. B.; Chibale, Kelly; Caira, Mino R.; CrystEngComm 16 (2014) 5781–; doi:10.1039/c3ce41798k

data_7216540
_publ_section_title
;
 Alternative solid-state forms of a potent antimalarial aminopyridine:
 X-ray crystallographic, thermal and solubility aspects
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5781
_journal_paper_doi               10.1039/c3ce41798k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H18 N3 O3 S, C4 H3 O4, C1 H4 O'
_chemical_formula_sum            'C23 H25 N3 O8 S'
_chemical_formula_weight         503.52
_chemical_melting_point          460
_chemical_name_systematic
; 
 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)-
pyridine-2-amine.(E)-butenedioate methanolate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.456(8)
_cell_angle_beta                 89.447(7)
_cell_angle_gamma                84.076(8)
_cell_formula_units_Z            2
_cell_length_a                   5.411(2)
_cell_length_b                   11.572(5)
_cell_length_c                   18.486(8)
_cell_measurement_reflns_used    4859
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      1.77
_cell_volume                     1150.2(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_molecular_graphics
;
Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXH-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa Apex II Duo diffractometer'
_diffrn_measurement_method       'phi- and omega-scans of 0.5 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23376
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.9190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            'translucent yellow'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.1079
_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^)+(0.1003P)^2^+5.4392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2707
_reflns_number_gt                3835
_reflns_number_total             4859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41798k.txt
_cod_data_source_block           c:\dyanne~1\2012\struct~1\007fap1_\bath\new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7216538--7216544.cif.
;
_cod_original_cell_volume        1150.2(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7216540