#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/19/2101939.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_2101939
loop_
_publ_author_name
'Verdonk, M. L.'
'Voogd, J. W.'
'Kanters, J. A.'
'Kroon, J.'
'den Besten, R.'
'Brandsma, L.'
'Leysen, D.'
'Kelder, J.'
_publ_section_title
;
 Structure and Serotonin 5-HT2C Receptor Activity of ortho-
 and meta-Substituted Phenylpiperazines
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              976
_journal_page_last               983
_journal_paper_doi               10.1107/S0108768197009142
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C11 H17 N2 O1 1+, C4 H3 O4 1-'
_chemical_formula_sum            'C15 H20 N2 O5'
_chemical_formula_weight         308.34
_chemical_name_systematic
;
 1-(3-methoxyphenyl)piperazine maleate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.325(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5086(11)
_cell_length_b                   9.0954(7)
_cell_length_c                   26.686(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.61
_cell_measurement_theta_min      3.96
_cell_volume                     1577.1(4)
_computing_cell_refinement       'SET4 (De Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1990a)'
_computing_molecular_graphics    'PLUTON (Spek, 1991)'
_computing_publication_material  'PLATON (Spek, 1990b)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'ω/2θ with Δω=0.91+0.35tanθ'
_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  0.0651
_diffrn_reflns_av_sigmaI/netI    0.2124
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2770
_diffrn_reflns_theta_max         24.14
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        3
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       platelet
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.858
_refine_ls_goodness_of_fit_obs   1.278
_refine_ls_hydrogen_treatment    'see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_restrained_S_obs      1.278
_refine_ls_R_factor_all          0.2664
_refine_ls_R_factor_obs          0.0759
_refine_ls_shift/esd_max         0.078
_refine_ls_shift/esd_mean        0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0759P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1947
_refine_ls_wR_factor_obs         0.1558
_reflns_number_observed          860
_reflns_number_total             2521
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha0157.cif
_cod_data_source_block           mMPP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w =
1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2101939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.2480(7) 0.5631(5) 0.3416(2) 0.0448(13) Uani d . 1 N
N2 0.1710(7) 0.4804(5) 0.4422(2) 0.0521(14) Uani d . 1 N
H21 0.1616(7) 0.4109(5) 0.4660(2) 0.104(6) Uiso calc R 1 H
H22 0.1459(7) 0.5683(5) 0.4561(2) 0.104(6) Uiso calc R 1 H
O12' -0.2444(7) 0.3884(5) 0.0346(2) 0.0601(13) Uani d . 1 O
O41' -0.2388(7) 0.6521(5) 0.0258(2) 0.0625(14) Uani d . 1 O
O11' -0.2409(7) 0.1950(5) -0.0151(2) 0.0681(15) Uani d . 1 O
O42' -0.2191(7) 0.8143(5) -0.0341(2) 0.0693(15) Uani d . 1 O
C2 0.1395(10) 0.6038(6) 0.2546(2) 0.049(2) Uani d . 1 C
H2 0.0304(10) 0.5393(6) 0.2582(2) 0.104(6) Uiso calc R 1 H
O3 0.0455(9) 0.6398(6) 0.1666(2) 0.088(2) Uani d . 1 O
C10 0.0396(9) 0.5673(8) 0.3602(2) 0.064(2) Uani d . 1 C
H101 -0.0612(9) 0.5485(8) 0.3328(2) 0.104(6) Uiso calc R 1 H
H102 0.0131(9) 0.6641(8) 0.3737(2) 0.104(6) Uiso calc R 1 H
C1 0.2773(9) 0.6367(6) 0.2966(2) 0.043(2) Uani d . 1 C
C9 0.0195(9) 0.4521(7) 0.4011(2) 0.050(2) Uani d . 1 C
H91 -0.1179(9) 0.4554(7) 0.4133(2) 0.104(6) Uiso calc R 1 H
H92 0.0413(9) 0.3549(7) 0.3874(2) 0.104(6) Uiso calc R 1 H
C2' -0.2657(10) 0.4225(7) -0.0539(2) 0.054(2) Uani d . 1 C
H2' -0.2828(10) 0.3713(7) -0.0840(2) 0.104(6) Uiso calc R 1 H
C3 0.1677(12) 0.6666(8) 0.2095(3) 0.063(2) Uani d . 1 C
C1' -0.2490(9) 0.3278(8) -0.0085(3) 0.049(2) Uani d . 1 C
C7 0.3996(10) 0.5921(7) 0.3827(2) 0.061(2) Uani d . 1 C
H71 0.3779(10) 0.6897(7) 0.3961(2) 0.104(6) Uiso calc R 1 H
H72 0.5369(10) 0.5885(7) 0.3704(2) 0.104(6) Uiso calc R 1 H
C3' -0.2604(10) 0.5689(7) -0.0589(2) 0.052(2) Uani d . 1 C
H3' -0.2734(10) 0.6024(7) -0.0918(2) 0.104(6) Uiso calc R 1 H
C6 0.4365(11) 0.7315(8) 0.2901(3) 0.068(2) Uani d . 1 C
H6 0.5290(11) 0.7559(8) 0.3167(3) 0.104(6) Uiso calc R 1 H
C8 0.3806(10) 0.4796(8) 0.4234(2) 0.070(2) Uani d . 1 C
H81 0.4105(10) 0.3828(8) 0.4105(2) 0.104(6) Uiso calc R 1 H
H82 0.4804(10) 0.5006(8) 0.4509(2) 0.104(6) Uiso calc R 1 H
C4 0.3281(15) 0.7586(10) 0.2028(3) 0.090(3) Uani d . 1 C
H4 0.3475(15) 0.7979(10) 0.1713(3) 0.104(6) Uiso calc R 1 H
C5 0.4562(13) 0.7919(8) 0.2412(3) 0.085(3) Uani d . 1 C
H5 0.5632(13) 0.8571(8) 0.2363(3) 0.104(6) Uiso calc R 1 H
C4' -0.2370(10) 0.6860(8) -0.0205(3) 0.058(2) Uani d . 1 C
C31 -0.1221(14) 0.5403(10) 0.1698(3) 0.108(3) Uani d . 1 C
H311 -0.1936(14) 0.5315(10) 0.1374(3) 0.104(6) Uiso calc R 1 H
H312 -0.2147(14) 0.5767(10) 0.1936(3) 0.104(6) Uiso calc R 1 H
H313 -0.0709(14) 0.4457(10) 0.1804(3) 0.104(6) Uiso calc R 1 H
H41' -0.264(12) 0.535(10) 0.030(3) 0.12(3) Uiso d . 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 C7 116.1(5) no
C1 N1 C10 116.9(5) no
C7 N1 C10 109.7(5) no
C9 N2 C8 109.9(5) no
C3 C2 C1 119.9(6) no
C3 O3 C31 118.1(6) no
N1 C10 C9 110.1(5) no
C6 C1 N1 123.6(6) no
C6 C1 C2 118.7(6) no
N1 C1 C2 117.6(6) no
N2 C9 C10 109.6(5) no
C3' C2' C1' 131.1(6) no
C2 C3 C4 121.5(7) no
C2 C3 O3 124.3(7) no
C4 C3 O3 114.2(7) no
O11' C1' O12' 123.9(7) no
O11' C1' C2' 117.2(7) no
O12' C1' C2' 118.9(6) no
N1 C7 C8 109.9(5) no
C2' C3' C4' 130.5(6) no
C1 C6 C5 117.8(7) no
N2 C8 C7 110.9(6) no
C5 C4 C3 119.6(8) no
C4 C5 C6 122.4(7) no
O42' C4' O41' 121.4(7) no
O42' C4' C3' 119.1(7) no
O41' C4' C3' 119.4(6) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.397(6) no
N1 C7 1.456(7) no
N1 C10 1.472(7) no
N2 C9 1.456(6) no
N2 C8 1.481(7) no
O12' C1' 1.276(7) no
O41' C4' 1.275(8) no
O11' C1' 1.222(6) no
O42' C4' 1.229(7) no
C2 C3 1.354(8) no
C2 C1 1.425(8) no
O3 C3 1.378(8) no
O3 C31 1.423(8) no
C10 C9 1.523(7) no
C1 C6 1.367(8) no
C2' C3' 1.339(8) no
C2' C1' 1.484(8) no
C3 C4 1.358(10) no
C7 C8 1.504(8) no
C3' C4' 1.479(9) no
C6 C5 1.429(9) no
C4 C5 1.318(10) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654463
