#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017263.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_2017263
loop_
_publ_author_name
'Polaske, Nathan W.'
'Nichol, Gary S.'
'Olenyuk, Bogdan'
_publ_section_title
;Polymorphism and phase transition behavior of
 6,6'-bis(chloromethyl)-1,1',4,4'-tetramethyl-3,3'-(p-phenylenedimethylene)bis(piperazine-2,5-dione)
;
_journal_coeditor_code           SK3332
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o381
_journal_page_last               o384
_journal_paper_doi               10.1107/S0108270109024457
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C22 H28 Cl2 N4 O4'
_chemical_formula_sum            'C22 H28 Cl2 N4 O4'
_chemical_formula_weight         483.38
_chemical_name_systematic
;
3,3'-[1,4-phenylene-bis-(methylene)]-bis-[6-(chloromethyl)-
1,4-dimethyl-2,5-piperazinedione]
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7566(5)
_cell_length_b                   12.7626(6)
_cell_length_c                   9.3138(4)
_cell_measurement_reflns_used    4706
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      2.19
_cell_volume                     1159.75(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009) and local
programs
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15349
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6409
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS 2008/1; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details 'Flack  (1983)'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0365
_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)+(0.0563P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1847
_reflns_number_total             2288
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3332.cif
_cod_data_source_block           2rt
_cod_database_code               2017263
_cod_database_fobs_code          2017263
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.84190(9) 0.45208(6) 0.16838(9) 0.0910(3) Uani d . 1 . .
O O1 0.5898(2) 0.35297(15) 0.4250(2) 0.0780(5) Uani d . 1 . .
O O2 0.89126(19) 0.12669(14) 0.0653(2) 0.0763(5) Uani d . 1 . .
N N1 0.7504(2) 0.22967(14) 0.3946(2) 0.0541(5) Uani d . 1 . .
N N2 0.7185(2) 0.23960(15) 0.0965(2) 0.0559(5) Uani d . 1 . .
C C1 0.6584(2) 0.29701(16) 0.3456(3) 0.0545(5) Uani d . 1 . .
C C2 0.8289(2) 0.15828(16) 0.3047(2) 0.0547(6) Uani d . 1 . .
H H2 0.9257 0.1682 0.3294 0.066 Uiso calc R 1 . .
C C3 0.8163(2) 0.17551(17) 0.1456(3) 0.0532(5) Uani d . 1 . .
C C4 0.6391(2) 0.30947(16) 0.1851(3) 0.0557(6) Uani d . 1 . .
H H4 0.5423 0.2954 0.1646 0.067 Uiso calc R 1 . .
C C5 0.6650(3) 0.4227(2) 0.1484(3) 0.0762(8) Uani d . 1 . .
H H5A 0.6114 0.4674 0.2113 0.091 Uiso calc R 1 . .
H H5B 0.6368 0.4362 0.0503 0.091 Uiso calc R 1 . .
C C6 0.7736(3) 0.2262(2) 0.5494(3) 0.0815(9) Uani d . 1 . .
H H6A 0.6907 0.2052 0.5969 0.122 Uiso calc R 1 . .
H H6B 0.8004 0.2944 0.5826 0.122 Uiso calc R 1 . .
H H6C 0.8449 0.1767 0.5703 0.122 Uiso calc R 1 . .
C C7 0.7009(4) 0.2486(2) -0.0583(3) 0.0839(9) Uani d . 1 . .
H H7A 0.7198 0.1822 -0.1026 0.126 Uiso calc R 1 . .
H H7B 0.7629 0.3005 -0.0951 0.126 Uiso calc R 1 . .
H H7C 0.6083 0.2690 -0.0792 0.126 Uiso calc R 1 . .
C C8 0.7935(3) 0.04213(18) 0.3380(3) 0.0670(6) Uani d . 1 . .
H H8A 0.8394 -0.0024 0.2687 0.080 Uiso calc R 1 . .
H H8B 0.8287 0.0245 0.4324 0.080 Uiso calc R 1 . .
C C9 0.6422(2) 0.01950(15) 0.3342(3) 0.0543(5) Uani d . 1 . .
C C10 0.5694(3) 0.0095(3) 0.4588(3) 0.0836(9) Uani d . 1 . .
H H10 0.6150 0.0158 0.5460 0.100 Uiso calc R 1 . .
C C11 0.5695(3) 0.0099(2) 0.2090(2) 0.0650(7) Uani d . 1 . .
H H11 0.6150 0.0169 0.1218 0.078 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 124.4(2) ?
C1 N1 C6 . . 117.8(2) ?
C2 N1 C6 . . 117.9(2) ?
C3 N2 C4 . . 124.5(2) ?
C3 N2 C7 . . 118.1(2) ?
C4 N2 C7 . . 117.0(2) ?
O1 C1 N1 . . 122.6(2) ?
O1 C1 C4 . . 117.8(2) ?
N1 C1 C4 . . 119.55(19) ?
N1 C2 H2 . . 106.9 ?
N1 C2 C3 . . 115.65(18) ?
N1 C2 C8 . . 111.45(19) ?
H2 C2 C3 . . 106.9 ?
H2 C2 C8 . . 106.9 ?
C3 C2 C8 . . 108.57(19) ?
O2 C3 N2 . . 122.1(2) ?
O2 C3 C2 . . 118.8(2) ?
N2 C3 C2 . . 119.0(2) ?
N2 C4 C1 . . 115.66(19) ?
N2 C4 H4 . . 107.0 ?
N2 C4 C5 . . 111.9(2) ?
C1 C4 H4 . . 107.0 ?
C1 C4 C5 . . 107.67(19) ?
H4 C4 C5 . . 107.0 ?
Cl1 C5 C4 . . 109.98(18) ?
Cl1 C5 H5A . . 109.7 ?
Cl1 C5 H5B . . 109.7 ?
C4 C5 H5A . . 109.7 ?
C4 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
N1 C6 H6A . . 109.5 ?
N1 C6 H6B . . 109.5 ?
N1 C6 H6C . . 109.5 ?
H6A C6 H6B . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C2 C8 H8A . . 108.9 ?
C2 C8 H8B . . 108.9 ?
C2 C8 C9 . . 113.35(18) ?
H8A C8 H8B . . 107.7 ?
H8A C8 C9 . . 108.9 ?
H8B C8 C9 . . 108.9 ?
C8 C9 C10 . . 120.5(2) ?
C8 C9 C11 . . 123.0(2) ?
C10 C9 C11 . . 116.5(2) ?
C9 C10 C10 . 2_655 121.87(15) ?
C9 C10 H10 . . 119.1 ?
C10 C10 H10 2_655 . 119.1 ?
C9 C11 C11 . 2_655 121.68(14) ?
C9 C11 H11 . . 119.2 ?
C11 C11 H11 2_655 . 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 . 1.776(3) ?
O1 C1 . 1.227(3) ?
O2 C3 . 1.218(3) ?
N1 C1 . 1.324(3) ?
N1 C2 . 1.455(3) ?
N1 C6 . 1.459(3) ?
N2 C3 . 1.338(3) ?
N2 C4 . 1.441(3) ?
N2 C7 . 1.456(3) ?
C1 C4 . 1.515(3) ?
C2 H2 . 0.980 ?
C2 C3 . 1.503(3) ?
C2 C8 . 1.553(3) ?
C4 H4 . 0.980 ?
C4 C5 . 1.507(3) ?
C5 H5A . 0.970 ?
C5 H5B . 0.970 ?
C6 H6A . 0.960 ?
C6 H6B . 0.960 ?
C6 H6C . 0.960 ?
C7 H7A . 0.960 ?
C7 H7B . 0.960 ?
C7 H7C . 0.960 ?
C8 H8A . 0.970 ?
C8 H8B . 0.970 ?
C8 C9 . 1.505(3) ?
C9 C10 . 1.366(3) ?
C9 C11 . 1.370(3) ?
C10 C10 2_655 1.375(6) ?
C10 H10 . 0.930 ?
C11 C11 2_655 1.379(5) ?
C11 H11 . 0.930 ?
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
C6 H6C O1 4_556 0.96 2.42 3.255(4) 145 y
C8 H8B O1 3_646 0.97 2.68 3.463(3) 138 y
C5 H5B O2 3_655 0.97 2.67 3.323(3) 125 y
C7 H7C O2 4_455 0.96 2.50 3.415(4) 158 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 176.8(2) ?
C2 N1 C1 C4 . . . . -5.5(3) ?
C6 N1 C1 O1 . . . . -2.6(3) ?
C6 N1 C1 C4 . . . . 175.2(2) ?
C1 N1 C2 C3 . . . . 9.1(3) ?
C1 N1 C2 C8 . . . . -115.5(2) ?
C6 N1 C2 C3 . . . . -171.6(2) ?
C6 N1 C2 C8 . . . . 63.8(3) ?
C4 N2 C3 O2 . . . . -171.5(2) ?
C4 N2 C3 C2 . . . . 12.2(3) ?
C7 N2 C3 O2 . . . . 1.2(3) ?
C7 N2 C3 C2 . . . . -175.1(2) ?
N1 C2 C3 O2 . . . . 171.6(2) ?
N1 C2 C3 N2 . . . . -12.0(3) ?
C8 C2 C3 O2 . . . . -62.3(3) ?
C8 C2 C3 N2 . . . . 114.1(2) ?
C3 N2 C4 C1 . . . . -8.0(3) ?
C3 N2 C4 C5 . . . . 115.8(3) ?
C7 N2 C4 C1 . . . . 179.2(2) ?
C7 N2 C4 C5 . . . . -57.0(3) ?
O1 C1 C4 N2 . . . . -177.97(19) ?
O1 C1 C4 C5 . . . . 56.0(3) ?
N1 C1 C4 N2 . . . . 4.2(3) ?
N1 C1 C4 C5 . . . . -121.9(2) ?
N2 C4 C5 Cl1 . . . . -58.2(2) ?
C1 C4 C5 Cl1 . . . . 70.0(2) ?
N1 C2 C8 C9 . . . . 51.9(3) ?
C3 C2 C8 C9 . . . . -76.6(3) ?
C2 C8 C9 C10 . . . . -102.6(3) ?
C2 C8 C9 C11 . . . . 76.0(3) ?
C8 C9 C10 C10 . . . 2_655 179.0(4) ?
C11 C9 C10 C10 . . . 2_655 0.2(5) ?
C8 C9 C11 C11 . . . 2_655 -179.4(3) ?
C10 C9 C11 C11 . . . 2_655 -0.7(4) ?
