Hydrogen-Bonding Stabilization of <i>N</i>-Methyldopamine 4-<i>O</i>-Dihydrogenphosphate in HCl Acidic Solution: Synthesis of Z2055, a New Dopaminergic Prodrug
Ianelli, S.; Nardelli, M.; Doggi, F.; Norcini, G.; Santangelo, F.; Acta Crystallographica Section C 51 (1995) 1338–1341; doi:10.1107/S0108270194014721

data_2003664
_publ_section_title
;
 Hydrogen-Bonding Stabilization of <i>N</i>-Methyldopamine
 4-<i>O</i>-Dihydrogenphosphate in HCl Acidic Solution: Synthesis of
 Z2055, a New Dopaminergic Prodrug
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1338
_journal_page_last               1341
_journal_paper_doi               10.1107/S0108270194014721
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source
;
chemical synthesis (see Comment)
;
_chemical_formula_analytical     'C9 H15 Cl N O5 P'
_chemical_formula_moiety         'C9 H15 Cl N O5 P'
_chemical_formula_sum            'C9 H15 Cl N O5 P'
_chemical_formula_weight         283.65
_chemical_melting_point          449.5(15)
_chemical_name_systematic
;
 4-[2-(methylamino)ethyl]-1,2-benzenediol 1-(dihydrogenphospate)
 hydrochloride
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.60(1)
_cell_length_b                   12.219(2)
_cell_length_c                   7.822(2)
_cell_measurement_radiation      CuK\a~1~
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.67
_cell_measurement_theta_min      14.06
_cell_measurement_wavelength     1.540562
_cell_volume                     2542.3(12)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia, 1984)'
_computing_data_collection       'local programs'
_computing_data_reduction        'local programs'
_computing_molecular_graphics
;
ORTEP (Johnson, 1965) and PLUTO (Motherwell & Clegg, 1978)
;
_computing_publication_material
;
PARST (Nardelli, 1983) and PARSTCIF (Nardelli, 1991)
;
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1995)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens AED'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  Ni-filtered
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_av_sigmaI/netI    0.1098
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4744
_diffrn_reflns_reduction_process
;
standard
;
_diffrn_reflns_theta_max         70.09
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        'no significant variation'
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    3.975
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description
;
very thin plates
;
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.667
_refine_ls_extinction_coef       0.001(0)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1995)'
_refine_ls_goodness_of_fit_all   1.270
_refine_ls_goodness_of_fit_obs   1.325
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.270
_refine_ls_restrained_S_obs      1.325
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_obs          0.1077
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;w = 1/[\s^2^(F~o~^2^) + (0.0756P)^2^ + 3.3468P]
 where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.2299
_refine_ls_wR_factor_obs         0.2085
_reflns_number_observed          1838
_reflns_number_total             2412
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ha1141.cif
_cod_data_source_block           X
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '448-451 K' was changed to
'449.5(15)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2542.0(10)
_cod_database_code               2003664