#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519950.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519950
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 1-Methylpiperazinium fumarate hemifumaric acid
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              554
_journal_year                    2008
_chemical_formula_sum            'C22 H36 N4 O12'
_chemical_formula_weight         548.55
_chemical_name_systematic
;
fumaric acid & 1-methylpiperazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.834(3)
_cell_angle_beta                 91.509(3)
_cell_angle_gamma                92.367(3)
_cell_formula_units_Z            1
_cell_length_a                   6.7452(3)
_cell_length_b                   8.7155(5)
_cell_length_c                   11.3058(6)
_cell_measurement_reflns_used    2815
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     649.55(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8705
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0761
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+1.6339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                2106
_reflns_number_total             2952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-554.cif
_cod_data_source_block           07skc0014
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/554)

More at:
http://ecrystals.chem.soton.ac.uk/554/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519950
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4063(4) 0.9642(3) 0.1273(3) 0.0175(6) Uani 1 1 d . . .
C2 C 0.5067(4) 0.8142(3) 0.1299(3) 0.0181(6) Uani 1 1 d . . .
H2 H 0.4632 0.7222 0.0730 0.022 Uiso 1 1 calc R . .
C3 C 0.6530(4) 0.8047(4) 0.2080(3) 0.0185(6) Uani 1 1 d . . .
H3 H 0.6994 0.8977 0.2629 0.022 Uiso 1 1 calc R . .
C4 C 0.7492(4) 0.6543(3) 0.2143(3) 0.0183(6) Uani 1 1 d . . .
O1A O 0.4730(3) 1.0883(2) 0.19832(19) 0.0194(5) Uani 1 1 d . . .
O1B O 0.2588(3) 0.9578(2) 0.05575(19) 0.0220(5) Uani 1 1 d . . .
O4A O 0.6926(3) 0.5314(2) 0.1401(2) 0.0223(5) Uani 1 1 d . . .
O4B O 0.8833(3) 0.6604(3) 0.2961(2) 0.0258(5) Uani 1 1 d . . .
C22 C 0.0713(4) 0.2983(4) 0.3223(3) 0.0180(6) Uani 1 1 d . . .
H22A H 0.0068 0.3976 0.3542 0.022 Uiso 1 1 calc R . .
H22B H 0.1003 0.2470 0.3909 0.022 Uiso 1 1 calc R . .
C23 C -0.0668(4) 0.1924(3) 0.2314(3) 0.0182(6) Uani 1 1 d . . .
H23A H -0.0069 0.0898 0.2046 0.022 Uiso 1 1 calc R . .
H23B H -0.1937 0.1740 0.2695 0.022 Uiso 1 1 calc R . .
N24 N -0.1056(4) 0.2648(3) 0.1248(2) 0.0181(5) Uani 1 1 d . . .
H24A H -0.1835 0.1958 0.0681 0.022 Uiso 1 1 calc R . .
H24B H -0.1746 0.3541 0.1487 0.022 Uiso 1 1 calc R . .
C25 C 0.0814(4) 0.3055(4) 0.0690(3) 0.0187(6) Uani 1 1 d . . .
H25A H 0.0501 0.3590 0.0021 0.022 Uiso 1 1 calc R . .
H25B H 0.1488 0.2082 0.0350 0.022 Uiso 1 1 calc R . .
C26 C 0.2182(4) 0.4113(3) 0.1615(3) 0.0184(6) Uani 1 1 d . . .
H26A H 0.3438 0.4343 0.1237 0.022 Uiso 1 1 calc R . .
H26B H 0.1551 0.5118 0.1915 0.022 Uiso 1 1 calc R . .
C27 C 0.4027(5) 0.4295(4) 0.3562(3) 0.0241(7) Uani 1 1 d . . .
H27A H 0.5256 0.4517 0.3172 0.036 Uiso 1 1 calc R . .
H27B H 0.4326 0.3720 0.4200 0.036 Uiso 1 1 calc R . .
H27C H 0.3432 0.5284 0.3917 0.036 Uiso 1 1 calc R . .
N21 N 0.2612(3) 0.3329(3) 0.2648(2) 0.0157(5) Uani 1 1 d . . .
H21 H 0.3182 0.2381 0.2344 0.040(11) Uiso 1 1 calc R . .
C31 C 0.7407(5) 1.1203(4) 0.5552(3) 0.0209(7) Uani 1 1 d . . .
C32 C 0.5745(5) 1.0009(4) 0.5392(3) 0.0223(7) Uani 1 1 d . . .
H32 H 0.5751 0.9229 0.5868 0.027 Uiso 1 1 calc R . .
O31A O 0.7498(3) 1.2263(3) 0.4999(2) 0.0258(5) Uani 1 1 d . . .
O31B O 0.8766(4) 1.0999(3) 0.6365(2) 0.0282(6) Uani 1 1 d . . .
H31B H 0.9577 1.1777 0.6510 0.060(15) Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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_site_symmetry_1
_geom_angle_site_symmetry_3
O1B C1 O1A 124.1(3) . .
O1B C1 C2 117.7(3) . .
O1A C1 C2 118.2(2) . .
C3 C2 C1 122.9(3) . .
C3 C2 H2 118.6 . .
C1 C2 H2 118.6 . .
C2 C3 C4 123.3(3) . .
C2 C3 H3 118.4 . .
C4 C3 H3 118.4 . .
O4A C4 O4B 124.3(3) . .
O4A C4 C3 118.8(3) . .
O4B C4 C3 116.9(3) . .
N21 C22 C23 110.4(2) . .
N21 C22 H22A 109.6 . .
C23 C22 H22A 109.6 . .
N21 C22 H22B 109.6 . .
C23 C22 H22B 109.6 . .
H22A C22 H22B 108.1 . .
N24 C23 C22 110.4(2) . .
N24 C23 H23A 109.6 . .
C22 C23 H23A 109.6 . .
N24 C23 H23B 109.6 . .
C22 C23 H23B 109.6 . .
H23A C23 H23B 108.1 . .
C25 N24 C23 111.9(2) . .
C25 N24 H24A 109.2 . .
C23 N24 H24A 109.2 . .
C25 N24 H24B 109.2 . .
C23 N24 H24B 109.2 . .
H24A N24 H24B 107.9 . .
N24 C25 C26 110.7(2) . .
N24 C25 H25A 109.5 . .
C26 C25 H25A 109.5 . .
N24 C25 H25B 109.5 . .
C26 C25 H25B 109.5 . .
H25A C25 H25B 108.1 . .
N21 C26 C25 109.7(2) . .
N21 C26 H26A 109.7 . .
C25 C26 H26A 109.7 . .
N21 C26 H26B 109.7 . .
C25 C26 H26B 109.7 . .
H26A C26 H26B 108.2 . .
N21 C27 H27A 109.5 . .
N21 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
N21 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C27 N21 C26 111.9(2) . .
C27 N21 C22 110.4(2) . .
C26 N21 C22 109.8(2) . .
C27 N21 H21 108.2 . .
C26 N21 H21 108.2 . .
C22 N21 H21 108.2 . .
O31A C31 O31B 124.0(3) . .
O31A C31 C32 123.3(3) . .
O31B C31 C32 112.7(3) . .
C32 C32 C31 122.2(4) 2_676 .
C32 C32 H32 118.9 2_676 .
C31 C32 H32 118.9 . .
C31 O31B H31B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1B 1.258(3) .
C1 O1A 1.265(4) .
C1 C2 1.502(4) .
C2 C3 1.324(4) .
C2 H2 0.9500 .
C3 C4 1.500(4) .
C3 H3 0.9500 .
C4 O4A 1.256(4) .
C4 O4B 1.268(4) .
C22 N21 1.498(4) .
C22 C23 1.505(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 N24 1.493(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
N24 C25 1.487(4) .
N24 H24A 0.9200 .
N24 H24B 0.9200 .
C25 C26 1.510(4) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 N21 1.497(4) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 N21 1.488(4) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
N21 H21 0.9300 .
C31 O31A 1.218(4) .
C31 O31B 1.324(4) .
C31 C32 1.479(4) .
C32 C32 1.320(6) 2_676
C32 H32 0.9500 .
O31B H31B 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 O1A 0.93 1.70 2.608(3) 165.7 1_545
O31B H31B O4B 0.84 1.73 2.563(3) 171.2 2_776
N24 H24A O1B 0.92 1.77 2.664(3) 161.9 2_565
N24 H24B O4A 0.92 1.84 2.719(3) 160.0 1_455
