#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2003385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003385
loop_
_publ_author_name
'Bombieri, G.'
'Del Pra, A.'
'Ayala, D. J.'
'Stradi, R.'
'Mantovanini, M.'
_publ_section_title
;
 (<i>S</i>)-({-})-3-(4-Phenyl-1-piperazinyl)-1,2-propanediol
 <i>N</i>,<i>N</i>'-Dioxide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              642
_journal_page_last               644
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C13 H20 N2 O4'
_chemical_formula_sum            'C13 H20 N2 O4'
_chemical_formula_weight         268.3
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   5.5180(10)
_cell_length_b                   13.059(5)
_cell_length_c                   18.246(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1314.8(6)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2916
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.36
_exptl_crystal_description       'irregular prism'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.59
_refine_ls_number_parameters     252
_refine_ls_number_reflns         1585
_refine_ls_R_factor_obs          0.030
_refine_ls_shift/esd_max         0.01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 1/[\s^2^(F~o~) + 0.004976(F~o~)^2^]'
_refine_ls_wR_factor_obs         0.033
_reflns_number_observed          1585
_reflns_number_total             2135
_reflns_observed_criterion       I~net~>2.5\s(I~net~)
_[local]_cod_data_source_file    na1115.cif
_[local]_cod_data_source_block   na1115a
_cod_original_cell_volume        1314.6(7)
_cod_database_code               2003385
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) .5354(3) .42390(10) .96230(10) .0298(6)
O(2) .0264(3) .30470(10) .79470(10) .0286(5)
O(12) -.2050(4) .1220(2) .91610(10) .0320(6)
O(16) .0695(4) -.0207(2) .76680(10) .0410(7)
N(1) .3832(3) .4630(2) .90830(10) .0228(6)
N(2) .1793(3) .27090(10) .84970(10) .0213(6)
C(1) .2415(5) .6312(2) .8598(2) .0336(9)
C(2) .2656(6) .7367(2) .8537(2) .0430(10)
C(3) .4483(6) .7866(2) .8905(2) .0450(10)
C(4) .6061(6) .7317(2) .9339(2) .0480(10)
C(5) .5831(5) .6268(2) .9415(2) .0361(9)
C(6) .4004(5) .5779(2) .90370(10) .0255(7)
C(7) .4580(5) .4188(2) .83540(10) .0278(8)
C(8) .4368(5) .3043(2) .8350(2) .0282(8)
C(9) .1050(5) .3151(2) .92270(10) .0222(7)
C(10) .1253(4) .4295(2) .9227(2) .0241(7)
C(11) .1780(5) .1553(2) .8516(2) .0260(8)
C(12) -.0709(5) .1069(2) .85060(10) .0241(7)
C(13) -.0482(6) -.0062(2) .8345(2) .0340(10)
H(1) .122(7) .595(3) .829(2) ?
H(2) .149(6) .772(2) .820(2) ?
H(3) .450(7) .861(3) .884(2) ?
H(4) .727(6) .765(2) .958(2) ?
H(5) .691(6) .582(2) .968(2) ?
H(12) -.122(6) .111(2) .949(2) ?
H(16) .047(7) -.074(3) .751(2) ?
H(71) .365(6) .451(2) .800(2) ?
H(72) .620(6) .438(2) .825(2) ?
H(81) .473(5) .280(2) .786(2) ?
H(82) .538(6) .270(2) .874(2) ?
H(91) -.053(6) .299(2) .9280(10) ?
H(92) .197(4) .283(2) .9590(10) ?
H(101) .081(4) .460(2) .9690(10) ?
H(102) .029(5) .462(2) .886(2) ?
H(111) .255(5) .134(2) .808(2) ?
H(112) .263(5) .137(2) .893(2) ?
H(121) -.173(4) .137(2) .8110(10) ?
H(131) -.206(5) -.038(2) .833(2) ?
H(132) .038(5) -.040(2) .873(2) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(1) N(1) C(10) 109.8(2) yes
O(1) N(1) C(6) 111.5(2) yes
C(6) N(1) C(10) 110.9(2) yes
O(2) N(2) C(11) 109.4(2) yes
O(2) N(2) C(8) 110.7(2) yes
C(8) N(2) C(11) 107.3(2) yes
C(2) C(1) C(6) 119.2(3) yes
C(2) C(3) C(4) 119.8(3) yes
C(4) C(5) C(6) 118.4(3) yes
N(1) C(6) C(5) 118.7(2) yes
N(1) C(7) C(8) 111.4(2) yes
N(2) C(9) C(10) 111.2(2) yes
N(2) C(11) C(12) 115.0(2) yes
C(11) C(12) C(13) 109.6(2) yes
O(16) C(13) C(12) 109.8(2) yes
O(1) N(1) C(7) 108.6(2) yes
C(7) N(1) C(10) 107.5(2) yes
C(6) N(1) C(7) 108.4(2) yes
O(2) N(2) C(9) 110.6(2) yes
C(9) N(2) C(11) 111.1(2) yes
C(8) N(2) C(9) 107.6(2) yes
C(1) C(2) C(3) 120.1(3) yes
C(3) C(4) C(5) 121.1(3) yes
C(1) C(6) C(5) 121.5(3) yes
N(1) C(6) C(1) 119.7(2) yes
N(2) C(8) C(7) 111.1(2) yes
N(1) C(10) C(9) 111.1(2) yes
O(12) C(12) C(11) 113.9(2) yes
O(12) C(12) C(13) 110.0(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) N(1) 1.392(3) yes
O(12) C(12) 1.420(3) yes
N(1) C(6) 1.505(3) yes
N(1) C(10) 1.512(3) yes
N(2) C(9) 1.509(3) yes
C(1) C(2) 1.388(4) yes
C(2) C(3) 1.376(5) yes
C(4) C(5) 1.383(4) yes
C(7) C(8) 1.500(4) yes
C(11) C(12) 1.511(4) yes
O(2) N(2) 1.383(3) yes
O(16) C(13) 1.408(4) yes
N(1) C(7) 1.507(3) yes
N(2) C(8) 1.510(3) yes
N(2) C(11) 1.510(3) yes
C(1) C(6) 1.376(4) yes
C(3) C(4) 1.378(5) yes
C(5) C(6) 1.379(4) yes
C(9) C(10) 1.498(4) yes
C(12) C(13) 1.512(4) yes