#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000415.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_2000415
loop_
_publ_author_name
'Verdonk, M. L.'
'Kanters, J. A.'
'Kroon, J.'
_publ_contact_author
;
Marcel L. Verdonk
Bijvoet Center for Biomolecular Research
Department of Crystal and Structural Chemistry
Utrecht University
Padualaan 8
3584 CH Utrecht
;
_publ_section_title
;
 Structure of eltoprazine
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2271
_journal_page_last               2273
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C12 H17 N2 O2 1+,(Cl 1-)1'
_chemical_formula_sum            'C12 H17 Cl N2 O2'
_chemical_formula_weight         256.73
_chemical_name_systematic
;
1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine hydrochloride
;
_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'
_audit_creation_method           'PLATON TABLE ACC option'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3150(10)
_cell_length_b                   7.941(2)
_cell_length_c                   21.393(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      18.01
_cell_measurement_theta_min      15.67
_cell_volume                     1242.7(4)
_computing_cell_refinement       'SET4 (de Boer, 1984)'
_computing_data_reduction        'HELENA (Spek, 1990a)'
_computing_molecular_graphics    'EUCLID (Spek, 1982)'
_computing_publication_material  'PLATON92 (Spek, 1990b)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       'Background-peak-background from \w/2\q scan'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.120
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2998
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         0.10
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.48
_refine_ls_goodness_of_fit_obs   1.41
_refine_ls_hydrogen_treatment
;
No hydrogen parameters were refined except for an overall
displacement parameter
;
_refine_ls_matrix_type           full
_refine_ls_number_constraints    51
_refine_ls_number_parameters     171
_refine_ls_number_reflns         850
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.069
_refine_ls_shift/esd_max         0.091
_refine_ls_shift/esd_mean        0.025
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/[\s^2^(F)+0.0004F^2^]
_refine_ls_wR_factor_obs         0.063
_reflns_number_observed          850
_reflns_number_total             2639
_reflns_observed_criterion       I>2.5\s(I)
_[local]_cod_data_source_file    ab1011.cif
_[local]_cod_data_source_block   eltoprazine
_[local]_cod_chemical_formula_sum_orig 'C12 H17 N2 O2 Cl1'
_cod_database_code               2000415
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 3
1 2 1
1 2 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
O 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1
N 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1
N 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1
Cl 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
O1 0.1400(10) 0.4225(8) 0.0017(3) 0.047(3) Uani
O2 0.4210(10) 0.4142(7) 0.0945(3) 0.035(2) Uani
N1 0.4980(10) 0.6923(9) 0.1637(3) 0.029(3) Uani
N2 0.8300(10) 0.7830(10) 0.2272(4) 0.040(3) Uani
C1 0.1760(10) 0.5580(10) 0.0392(4) 0.027(3) Uani
C2 0.2750(10) 0.2890(10) 0.0058(5) 0.041(4) Uani
C3 0.329(2) 0.2640(10) 0.0716(4) 0.037(4) Uani
C4 0.3120(10) 0.5560(10) 0.0840(4) 0.029(3) Uani
C5 0.3470(10) 0.7000(10) 0.1203(4) 0.029(3) Uani
C6 0.2360(10) 0.8370(10) 0.1130(5) 0.040(4) Uani
C7 0.0950(10) 0.8340(10) 0.0701(4) 0.037(4) Uani
C8 0.0650(10) 0.7010(10) 0.0331(5) 0.036(4) Uani
C9 0.502(2) 0.8310(10) 0.2085(4) 0.041(4) Uani
C10 0.6470(10) 0.8050(10) 0.2568(4) 0.042(4) Uani
C11 0.8240(10) 0.6420(10) 0.1808(5) 0.034(3) Uani
C12 0.6780(10) 0.6770(10) 0.1325(4) 0.035(3) Uani
Cl1 0.8903(4) 0.1561(3) 0.17850(10) 0.0490(10) Uani
H1 0.867 0.898 0.2035 0.056(7) Uiso
H2 0.930 0.755 0.2628 0.056(7) Uiso
H3 0.217 0.174 -0.0123 0.056(7) Uiso
H4 0.394 0.324 -0.0214 0.056(7) Uiso
H5 0.421 0.158 0.0747 0.056(7) Uiso
H6 0.209 0.240 0.0995 0.056(7) Uiso
H7 0.258 0.948 0.1411 0.056(7) Uiso
H8 0.007 0.942 0.0662 0.056(7) Uiso
H9 -0.044 0.703 -0.0010 0.056(7) Uiso
H10 0.530 0.947 0.1838 0.056(7) Uiso
H11 0.371 0.840 0.2313 0.056(7) Uiso
H12 0.615 0.694 0.2836 0.056(7) Uiso
H13 0.651 0.913 0.2874 0.056(7) Uiso
H14 0.955 0.630 0.1579 0.056(7) Uiso
H15 0.792 0.525 0.2048 0.056(7) Uiso
H16 0.673 0.575 0.0991 0.056(7) Uiso
H17 0.709 0.793 0.1086 0.056(7) Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.037(5) 0.047(4) 0.058(5) -0.001(4) -0.009(4) -0.018(4)
O2 0.036(5) 0.021(3) 0.048(4) 0.001(4) -0.005(4) -0.001(3)
N1 0.042(5) 0.016(4) 0.030(5) 0.005(4) 0.000(4) -0.008(4)
N2 0.045(6) 0.040(5) 0.034(5) -0.002(5) -0.019(5) 0.000(4)
C1 0.026(6) 0.041(7) 0.013(5) 0.001(6) -0.002(5) 0.001(5)
C2 0.033(7) 0.043(7) 0.046(7) 0.000(6) 0.004(6) -0.014(6)
C3 0.034(7) 0.036(6) 0.040(6) 0.007(6) 0.014(6) 0.001(5)
C4 0.026(6) 0.027(6) 0.034(6) 0.008(5) 0.013(5) 0.008(5)
C5 0.028(6) 0.028(6) 0.032(6) -0.009(5) 0.006(5) 0.004(5)
C6 0.045(7) 0.022(5) 0.052(7) -0.006(7) 0.000(6) 0.000(6)
C7 0.033(7) 0.039(6) 0.038(6) 0.001(7) 0.009(6) 0.011(6)
C8 0.026(7) 0.039(7) 0.043(7) 0.003(6) -0.008(6) 0.008(5)
C9 0.045(7) 0.045(6) 0.033(6) -0.001(7) -0.004(6) 0.009(6)
C10 0.053(8) 0.034(6) 0.040(6) -0.011(6) -0.003(6) -0.004(5)
C11 0.024(5) 0.034(5) 0.044(6) 0.007(6) 0.003(6) -0.010(6)
C12 0.019(6) 0.046(6) 0.039(6) -0.002(6) 0.013(5) -0.016(6)
Cl1 0.052(2) 0.0370(10) 0.059(2) -0.009(2) -0.014(2) -0.002(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.370(10) yes
O1 C2 . . 1.450(10) yes
O2 C3 . . 1.450(10) yes
O2 C4 . . 1.400(10) yes
N1 C5 . . 1.440(10) yes
N1 C9 . . 1.460(10) yes
N1 C12 . . 1.480(10) yes
N2 C10 . . 1.490(10) yes
N2 C11 . . 1.500(10) yes
C1 C4 . . 1.380(10) yes
C1 C8 . . 1.400(10) yes
C2 C3 . . 1.480(10) yes
C4 C5 . . 1.410(10) yes
C5 C6 . . 1.370(10) yes
C6 C7 . . 1.380(10) yes
C7 C8 . . 1.340(10) yes
C9 C10 . . 1.500(10) yes
C11 C12 . . 1.510(10) yes
N2 H1 . . 1.08 no
N2 H2 . . 1.08 no
C2 H3 . . 1.08 no
C2 H4 . . 1.08 no
C3 H5 . . 1.08 no
C3 H6 . . 1.08 no
C6 H7 . . 1.08 no
C7 H8 . . 1.08 no
C8 H9 . . 1.08 no
C9 H10 . . 1.08 no
C9 H11 . . 1.08 no
C10 H12 . . 1.08 no
C10 H13 . . 1.08 no
C11 H14 . . 1.08 no
C11 H15 . . 1.09 no
C12 H16 . . 1.08 no
C12 H17 . . 1.08 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 . . . 114.1(7) yes
C3 O2 C4 . . . 110.0(7) yes
C5 N1 C9 . . . 113.9(8) yes
C5 N1 C12 . . . 113.2(6) yes
C9 N1 C12 . . . 109.9(8) yes
C10 N2 C11 . . . 110.1(6) yes
O1 C1 C4 . . . 122.4(7) yes
O1 C1 C8 . . . 118.1(7) yes
C4 C1 C8 . . . 119.4(8) yes
O1 C2 C3 . . . 109.8(8) yes
O2 C3 C2 . . . 109.6(7) yes
O2 C4 C1 . . . 122.1(7) yes
O2 C4 C5 . . . 117.6(7) yes
C1 C4 C5 . . . 120.3(7) yes
N1 C5 C4 . . . 117.4(7) yes
N1 C5 C6 . . . 124.2(8) yes
C4 C5 C6 . . . 118.4(7) yes
C5 C6 C7 . . . 120.4(8) yes
C6 C7 C8 . . . 122.0(7) yes
C1 C8 C7 . . . 119.3(8) yes
N1 C9 C10 . . . 111.3(8) yes
N2 C10 C9 . . . 111.1(8) yes
N2 C11 C12 . . . 109.7(6) yes
N1 C12 C11 . . . 109.6(7) yes
C10 N2 H1 . . . 109.0 no
C10 N2 H2 . . . 109.5 no
C11 N2 H1 . . . 109.2 no
C11 N2 H2 . . . 109.5 no
H1 N2 H2 . . . 109.6 no
O1 C2 H3 . . . 109.2 no
O1 C2 H4 . . . 109.1 no
C3 C2 H3 . . . 109.5 no
C3 C2 H4 . . . 109 no
H3 C2 H4 . . . 110 no
O2 C3 H5 . . . 109 no
O2 C3 H6 . . . 109.6 no
C2 C3 H5 . . . 109.3 no
C2 C3 H6 . . . 110 no
H5 C3 H6 . . . 110 no
C5 C6 H7 . . . 119.9 no
C7 C6 H7 . . . 119.7 no
C6 C7 H8 . . . 119.0 no
C8 C7 H8 . . . 119.0 no
C1 C8 H9 . . . 120.1 no
C7 C8 H9 . . . 120.6 no
N1 C9 H10 . . . 109.0 no
N1 C9 H11 . . . 109 no
C10 C9 H10 . . . 109 no
C10 C9 H11 . . . 109.1 no
H10 C9 H11 . . . 109 no
N2 C10 H12 . . . 109.0 no
N2 C10 H13 . . . 109.0 no
C9 C10 H12 . . . 109.1 no
C9 C10 H13 . . . 109.2 no
H12 C10 H13 . . . 109 no
N2 C11 H14 . . . 109.9 no
N2 C11 H15 . . . 109 no
C12 C11 H14 . . . 109 no
C12 C11 H15 . . . 109.1 no
H14 C11 H15 . . . 109.3 no
N1 C12 H16 . . . 109.2 no
N1 C12 H17 . . . 109.3 no
C11 C12 H16 . . . 109.8 no
C11 C12 H17 . . . 109.4 no
H16 C12 H17 . . . 110 no
_journal_paper_doi 10.1107/S0108270192008904