#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239453.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_2239453
loop_
_publ_author_name
'Zhou, Mi'
'Shao, Ying'
'Xia, Yong-an'
'Liu, Xiao-Long'
'Sun, Xiao-Qiang'
_publ_section_title
;
 2-[2-(4-Methylpiperazin-1-yl)ethyl]isoindoline-1,3-dione
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o287
_journal_paper_doi               10.1107/S1600536814002232
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C15 H19 N3 O2'
_chemical_formula_moiety         'C15 H19 N3 O2'
_chemical_formula_sum            'C15 H19 N3 O2'
_chemical_formula_weight         273.33
_chemical_name_systematic
;
2-[2-(4-Methylpiperazin-1-yl)ethyl]isoindoline-1,3-dione
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.260(4)
_cell_angle_beta                 98.381(4)
_cell_angle_gamma                92.647(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9537(12)
_cell_length_b                   8.4410(15)
_cell_length_c                   12.563(2)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.77
_cell_volume                     723.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'APEX2 (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4194
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.177
_refine_ls_extinction_coef       0.074(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0467
_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)+(0.0987P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                2206
_reflns_number_total             2654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7071sup1.cif
_cod_data_source_block           I
_cod_database_code               2239453
_cod_database_fobs_code          2239453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.7472(2) 0.1040(2) 0.64462(16) 0.0663(5) Uani d . 1 1
H H1 0.7495 0.1864 0.7004 0.080 Uiso calc R 1 1
C C2 0.7384(3) -0.0535(3) 0.6639(2) 0.0853(7) Uani d . 1 1
H H2 0.7335 -0.0780 0.7339 0.102 Uiso calc R 1 1
C C3 0.7366(3) -0.1743(3) 0.5820(3) 0.0952(9) Uani d . 1 1
H H3 0.7321 -0.2795 0.5976 0.114 Uiso calc R 1 1
C C4 0.7415(3) -0.1437(2) 0.4756(2) 0.0866(8) Uani d . 1 1
H H4 0.7398 -0.2263 0.4200 0.104 Uiso calc R 1 1
C C5 0.7489(2) 0.0147(2) 0.45574(15) 0.0583(5) Uani d . 1 1
C C6 0.75250(19) 0.13529(18) 0.53922(13) 0.0490(4) Uani d . 1 1
C C7 0.7637(2) 0.28929(18) 0.49368(12) 0.0470(4) Uani d . 1 1
C C8 0.7547(2) 0.0895(2) 0.35403(15) 0.0623(5) Uani d . 1 1
C C9 0.7949(2) 0.3733(3) 0.31185(14) 0.0682(5) Uani d . 1 1
H H9A 0.8471 0.3229 0.2500 0.082 Uiso calc R 1 1
H H9B 0.8920 0.4539 0.3501 0.082 Uiso calc R 1 1
C C10 0.6130(3) 0.4551(2) 0.27092(14) 0.0618(5) Uani d . 1 1
H H10A 0.5547 0.4975 0.3328 0.074 Uiso calc R 1 1
H H10B 0.6512 0.5447 0.2348 0.074 Uiso calc R 1 1
C C11 0.5329(2) 0.3035(2) 0.09326(13) 0.0585(4) Uani d . 1 1
H H11A 0.6436 0.2385 0.1059 0.070 Uiso calc R 1 1
H H11B 0.5750 0.3973 0.0624 0.070 Uiso calc R 1 1
C C12 0.3737(3) 0.2097(2) 0.01439(13) 0.0613(5) Uani d . 1 1
H H12A 0.4212 0.1801 -0.0534 0.074 Uiso calc R 1 1
H H12B 0.3373 0.1124 0.0431 0.074 Uiso calc R 1 1
C C13 0.1346(2) 0.3462(2) 0.09674(13) 0.0534(4) Uani d . 1 1
H H13A 0.0968 0.2504 0.1267 0.064 Uiso calc R 1 1
H H13B 0.0211 0.4083 0.0848 0.064 Uiso calc R 1 1
C C14 0.2917(2) 0.44238(19) 0.17559(12) 0.0532(4) Uani d . 1 1
H H14A 0.3254 0.5402 0.1467 0.064 Uiso calc R 1 1
H H14B 0.2430 0.4712 0.2432 0.064 Uiso calc R 1 1
C C15 0.0515(3) 0.2147(3) -0.08443(17) 0.0777(6) Uani d . 1 1
H H15A 0.0143 0.1167 -0.0585 0.117 Uiso calc R 1 1
H H15B 0.0996 0.1915 -0.1519 0.117 Uiso calc R 1 1
H H15C -0.0595 0.2779 -0.0951 0.117 Uiso calc R 1 1
N N1 0.46613(18) 0.35309(15) 0.19655(9) 0.0484(3) Uani d . 1 1
N N2 0.20302(19) 0.30264(16) -0.00548(10) 0.0541(4) Uani d . 1 1
N N3 0.76325(17) 0.25325(17) 0.38367(10) 0.0521(4) Uani d . 1 1
O O1 0.77364(19) 0.42351(14) 0.54040(10) 0.0671(4) Uani d . 1 1
O O2 0.7541(2) 0.0268(2) 0.26330(12) 0.0968(6) Uani d . 1 1
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
C2 C1 C6 117.6(2)
C2 C1 H1 121.2
C6 C1 H1 121.2
C3 C2 C1 121.1(2)
C3 C2 H2 119.4
C1 C2 H2 119.4
C2 C3 C4 121.6(2)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 117.5(2)
C5 C4 H4 121.3
C3 C4 H4 121.3
C6 C5 C4 120.36(19)
C6 C5 C8 107.93(15)
C4 C5 C8 131.71(19)
C5 C6 C1 121.86(17)
C5 C6 C7 107.87(15)
C1 C6 C7 130.27(15)
O1 C7 N3 124.58(15)
O1 C7 C6 128.68(14)
N3 C7 C6 106.73(13)
O2 C8 N3 124.7(2)
O2 C8 C5 129.28(19)
N3 C8 C5 106.01(14)
N3 C9 C10 114.32(13)
N3 C9 H9A 108.7
C10 C9 H9A 108.7
N3 C9 H9B 108.7
C10 C9 H9B 108.7
H9A C9 H9B 107.6
N1 C10 C9 114.94(15)
N1 C10 H10A 108.5
C9 C10 H10A 108.5
N1 C10 H10B 108.5
C9 C10 H10B 108.5
H10A C10 H10B 107.5
N1 C11 C12 111.26(13)
N1 C11 H11A 109.4
C12 C11 H11A 109.4
N1 C11 H11B 109.4
C12 C11 H11B 109.4
H11A C11 H11B 108.0
N2 C12 C11 111.05(14)
N2 C12 H12A 109.4
C11 C12 H12A 109.4
N2 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
N2 C13 C14 110.46(13)
N2 C13 H13A 109.6
C14 C13 H13A 109.6
N2 C13 H13B 109.6
C14 C13 H13B 109.6
H13A C13 H13B 108.1
N1 C14 C13 111.53(13)
N1 C14 H14A 109.3
C13 C14 H14A 109.3
N1 C14 H14B 109.3
C13 C14 H14B 109.3
H14A C14 H14B 108.0
N2 C15 H15A 109.5
N2 C15 H15B 109.5
H15A C15 H15B 109.5
N2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C10 N1 C14 108.35(13)
C10 N1 C11 112.08(13)
C14 N1 C11 108.84(12)
C13 N2 C15 111.53(14)
C13 N2 C12 108.61(12)
C15 N2 C12 111.25(13)
C7 N3 C8 111.45(15)
C7 N3 C9 123.36(15)
C8 N3 C9 124.69(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(3)
C1 C6 1.384(3)
C1 H1 0.9300
C2 C3 1.366(4)
C2 H2 0.9300
C3 C4 1.394(4)
C3 H3 0.9300
C4 C5 1.386(3)
C4 H4 0.9300
C5 C6 1.376(2)
C5 C8 1.490(3)
C6 C7 1.480(2)
C7 O1 1.2120(19)
C7 N3 1.382(2)
C8 O2 1.202(2)
C8 N3 1.388(2)
C9 N3 1.458(2)
C9 C10 1.519(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N1 1.457(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 N1 1.466(2)
C11 C12 1.504(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 N2 1.459(2)
C12 H12A 0.9700
C12 H12B 0.9700
C13 N2 1.450(2)
C13 C14 1.503(2)
C13 H13A 0.9700
C13 H13B 0.9700
C14 N1 1.464(2)
C14 H14A 0.9700
C14 H14B 0.9700
C15 N2 1.451(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O1 1_545 0.93 2.57 3.406(3) 149 yes
C15 H15B O2 2_655 0.96 2.53 3.343(3) 142 yes
