Stereochemistry of serotonin receptor ligands from crystallographic data. Crystal structures of NAN-190.HBr, 1-phenylbiguanide, MDL 72222 and mianserin.HCl and selectivity criteria towards 5-HT~1~, 5-HT~2~ and 5-HT~3~ receptor subtypes
Dalpiaz, A.; Ferretti, V.; Gilli, P.; Bertolasi, V.; Acta Crystallographica Section B 52 (1996) 509–518; doi:10.1107/S0108768195014765

data_2101531
_publ_section_title
;
 Stereochemistry of serotonin receptor ligands from crystallographic
 data. Crystal structures of NAN-190.HBr, 1-phenylbiguanide, MDL 72222
 and mianserin.HCl and selectivity criteria towards 5-HT~1~, 5-HT~2~
 and 5-HT~3~ receptor subtypes
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              509
_journal_page_last               518
_journal_paper_doi               10.1107/S0108768195014765
_journal_volume                  52
_journal_year                    1996
_chemical_formula_analytical     ' C23 H29 N3 O3.5 Br'
_chemical_formula_moiety         ' C23 H28 N3 O 3+, Br 1-, 0.5H2 O'
_chemical_formula_sum            'C23 H29 Br N3 O3.5'
_chemical_formula_weight         483.42
_chemical_melting_point          513.6(15)
_chemical_name_systematic
;
1-(2-Methoxyphenyl)-4-[-(2-phtalimido)butylpiperazine
hydrobromide emihydrate (NAN-190.HBr)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           'Cromer & Waber (1974)'
_cell_angle_alpha                90.00000
_cell_angle_beta                 101.560(10)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   21.916(4)
_cell_length_b                   15.207(2)
_cell_length_c                   14.052(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     4588.2(12)
_computing_cell_refinement       'CAD4 Enraf-Nonius Software, 1984'
_computing_data_collection       'CAD4 Enraf-Nonius Software, 1984'
_computing_data_reduction        'MolEN, C.K. Fair, Enraf-Nonius, 1990'
_computing_molecular_graphics    'ORTEPII, Johnson, 1976'
_computing_publication_material
;
 PARST (Nardelli, 1983); PARSTCIF (Nardelli, 1991)
;
_computing_structure_refinement  MolEN
_computing_structure_solution    'SIR88, Burla et al., 1989'
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5765
_diffrn_reflns_reduction_process
;
......
;
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.40
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2008.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.37
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         2617
_refine_ls_R_factor_obs          0.035
_refine_ls_shift/esd_max         0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4F^2^/[\s^2^(F^2^) + (0.03F^2^)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.036
_reflns_number_observed          2617
_reflns_number_total             5540
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            na0073.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '239-242 C' was changed to
'513.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '239-242 C' was changed to
'513.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 4F^2^/[\s^2^(F^2^) +
(0.03F^2^)^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4F^2^/[\s^2^(F^2^) + (0.03F^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4588.0(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        ' C23 H29 N3 O3.5 Br '
_cod_database_code               2101531