#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230770.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_2230770
loop_
_publ_author_name
'Wang, Jian'
'Liu, Weiwei'
'Guan, Tongwei'
'Yin, Fujun'
'Sun, Yuxi'
_publ_section_title
;
 2,5-Bis[(3-hydroxypropyl)amino]-1,4-benzoquinone monohydrate
;
_journal_coeditor_code           LD2011
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1632
_journal_paper_doi               10.1107/S1600536811021635
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H18 N2 O4, H2 O'
_chemical_formula_moiety         'C12 H18 N2 O4, H2 O'
_chemical_formula_sum            'C12 H20 N2 O5'
_chemical_formula_weight         272.30
_chemical_melting_point_gt       437.1
_chemical_melting_point_lt       438.3
_chemical_name_systematic
;
2,5-Bis[(3-hydroxypropyl)amino]-1,4-benzoquinone monohydrate
;
_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                82.104(2)
_cell_angle_beta                 87.994(2)
_cell_angle_gamma                80.849(2)
_cell_formula_units_Z            2
_cell_length_a                   4.9272(8)
_cell_length_b                   11.673(2)
_cell_length_c                   11.933(2)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.64
_cell_volume                     671.11(19)
_computing_cell_refinement       'SAINT (Bruker, 1996)'
_computing_data_collection       'SMART (Bruker, 1996)'
_computing_data_reduction        'SAINT (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega 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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5966
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0453
_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)+(0.0454P)²+0.0971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1963
_reflns_number_total             2895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ld2011.cif
_cod_data_source_block           I
_cod_original_cell_volume        671.13(19)
_cod_database_code               2230770
_cod_database_fobs_code          2230770
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.6153(3) -0.11927(12) 0.36773(12) 0.0390(4) Uani d D 1 1 . .
N N2 1.3092(3) 0.13162(11) 0.10709(11) 0.0351(3) Uani d D 1 1 . .
O O1 1.2722(3) -0.08231(10) 0.07011(10) 0.0453(3) Uani d . 1 1 . .
O O2 0.6703(3) 0.09049(10) 0.41065(10) 0.0552(4) Uani d . 1 1 . .
O O3 0.5303(4) -0.32465(13) 0.60246(12) 0.0736(5) Uani d D 1 1 . .
O O4 1.0113(3) 0.41209(12) -0.14943(12) 0.0565(4) Uani d D 1 1 . .
O O5 0.5089(3) 0.49169(15) 0.21551(15) 0.0768(5) Uani d D 1 1 . .
C C1 1.1245(3) -0.04600(13) 0.14826(13) 0.0314(4) Uani d . 1 1 . .
C C2 0.9446(3) -0.11051(13) 0.21472(13) 0.0340(4) Uani d . 1 1 . .
H H2A 0.9286 -0.1851 0.1994 0.041 Uiso calc R 1 1 . .
C C3 0.7922(3) -0.06574(13) 0.30165(13) 0.0317(4) Uani d . 1 1 . .
C C4 0.8147(3) 0.05513(13) 0.32951(13) 0.0351(4) Uani d . 1 1 . .
C C5 0.9895(3) 0.12030(13) 0.26347(13) 0.0349(4) Uani d . 1 1 . .
H H5 1.0042 0.1949 0.2793 0.042 Uiso calc R 1 1 . .
C C6 1.1415(3) 0.07683(12) 0.17496(13) 0.0293(3) Uani d . 1 1 . .
C C7 0.5507(4) -0.23474(14) 0.35927(14) 0.0396(4) Uani d . 1 1 . .
H H7A 0.5450 -0.2441 0.2799 0.048 Uiso calc R 1 1 . .
H H7B 0.3688 -0.2399 0.3915 0.048 Uiso calc R 1 1 . .
C C8 0.7530(4) -0.33485(14) 0.41825(14) 0.0435(4) Uani d . 1 1 . .
H H8A 0.6915 -0.4084 0.4109 0.052 Uiso calc R 1 1 . .
H H8B 0.9311 -0.3353 0.3809 0.052 Uiso calc R 1 1 . .
C C9 0.7835(5) -0.32661(18) 0.54126(16) 0.0589(6) Uani d . 1 1 . .
H H9A 0.9135 -0.3930 0.5742 0.071 Uiso calc R 1 1 . .
H H9B 0.8582 -0.2560 0.5486 0.071 Uiso calc R 1 1 . .
C C10 1.3668(4) 0.24973(13) 0.10990(14) 0.0380(4) Uani d . 1 1 . .
H H10A 1.5559 0.2458 0.1321 0.046 Uiso calc R 1 1 . .
H H10B 1.2486 0.2859 0.1662 0.046 Uiso calc R 1 1 . .
C C11 1.3213(3) 0.32460(13) -0.00383(13) 0.0339(4) Uani d . 1 1 . .
H H11A 1.3914 0.3974 -0.0017 0.041 Uiso calc R 1 1 . .
H H11B 1.4254 0.2842 -0.0612 0.041 Uiso calc R 1 1 . .
C C12 1.0238(3) 0.35224(14) -0.03697(14) 0.0382(4) Uani d . 1 1 . .
H H12A 0.9458 0.2806 -0.0334 0.046 Uiso calc R 1 1 . .
H H12B 0.9203 0.4011 0.0142 0.046 Uiso calc R 1 1 . .
H H5A 0.516(5) 0.4429(17) 0.2754(14) 0.092(8) Uiso d D 1 1 . .
H H5B 0.662(3) 0.516(2) 0.205(2) 0.099(9) Uiso d D 1 1 . .
H H2 1.405(4) 0.0890(14) 0.0584(13) 0.059(6) Uiso d D 1 1 . .
H H1 0.535(4) -0.0797(15) 0.4219(13) 0.063(6) Uiso d D 1 1 . .
H H4 0.844(4) 0.437(2) -0.167(2) 0.087(8) Uiso d D 1 1 . .
H H3 0.456(5) -0.2541(16) 0.601(2) 0.097(9) Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C7 . . 125.40(14) ?
C3 N1 H1 . . 115.3(13) ?
C7 N1 H1 . . 119.3(13) ?
C6 N2 C10 . . 126.63(14) ?
C6 N2 H2 . . 115.3(12) ?
C10 N2 H2 . . 117.9(12) ?
C9 O3 H3 . . 108.2(18) ?
C12 O4 H4 . . 109.4(17) ?
H5A O5 H5B . . 109.4(18) ?
O1 C1 C2 . . 124.65(14) ?
O1 C1 C6 . . 117.67(13) ?
C2 C1 C6 . . 117.68(13) ?
C3 C2 C1 . . 121.45(14) ?
C3 C2 H2A . . 119.3 ?
C1 C2 H2A . . 119.3 ?
N1 C3 C2 . . 125.71(15) ?
N1 C3 C4 . . 113.62(13) ?
C2 C3 C4 . . 120.67(13) ?
O2 C4 C5 . . 124.28(15) ?
O2 C4 C3 . . 117.34(14) ?
C5 C4 C3 . . 118.38(13) ?
C6 C5 C4 . . 121.53(14) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
N2 C6 C5 . . 126.20(14) ?
N2 C6 C1 . . 113.53(13) ?
C5 C6 C1 . . 120.27(13) ?
N1 C7 C8 . . 114.31(14) ?
N1 C7 H7A . . 108.7 ?
C8 C7 H7A . . 108.7 ?
N1 C7 H7B . . 108.7 ?
C8 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C9 C8 C7 . . 112.93(15) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
O3 C9 C8 . . 112.68(18) ?
O3 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
O3 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
N2 C10 C11 . . 111.84(13) ?
N2 C10 H10A . . 109.2 ?
C11 C10 H10A . . 109.2 ?
N2 C10 H10B . . 109.2 ?
C11 C10 H10B . . 109.2 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 113.21(13) ?
C12 C11 H11A . . 108.9 ?
C10 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C10 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
O4 C12 C11 . . 107.74(13) ?
O4 C12 H12A . . 110.2 ?
C11 C12 H12A . . 110.2 ?
O4 C12 H12B . . 110.2 ?
C11 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
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
N1 C3 . 1.3273(19) ?
N1 C7 . 1.451(2) ?
N1 H1 . 0.891(9) ?
N2 C6 . 1.3140(19) ?
N2 C10 . 1.456(2) ?
N2 H2 . 0.891(9) ?
O1 C1 . 1.2419(17) ?
O2 C4 . 1.2580(18) ?
O3 C9 . 1.422(2) ?
O3 H3 . 0.844(16) ?
O4 C12 . 1.424(2) ?
O4 H4 . 0.850(16) ?
O5 H5A . 0.849(9) ?
O5 H5B . 0.849(9) ?
C1 C2 . 1.407(2) ?
C1 C6 . 1.526(2) ?
C2 C3 . 1.372(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.515(2) ?
C4 C5 . 1.392(2) ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.519(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.499(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.513(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.504(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
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
O5 H5B O4 2_765 0.849(9) 1.982(10) 2.818(2) 168(2)
O5 H5A O3 2_656 0.849(9) 1.899(10) 2.736(2) 169(2)
O3 H3 O2 2_656 0.844(16) 1.900(17) 2.7398(19) 173(3)
N1 H1 O2 2_656 0.891(9) 2.204(14) 2.9865(18) 146.2(17)
N2 H2 O1 2_855 0.891(9) 2.170(13) 2.9508(17) 146.0(17)
O4 H4 O5 2_665 0.850(16) 1.881(17) 2.727(2) 173(2)
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
O1 C1 C2 C3 . . . . 178.39(16) ?
C6 C1 C2 C3 . . . . -0.9(2) ?
C7 N1 C3 C2 . . . . -0.3(3) ?
C7 N1 C3 C4 . . . . 179.25(15) ?
C1 C2 C3 N1 . . . . 179.10(16) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
N1 C3 C4 O2 . . . . 0.8(2) ?
C2 C3 C4 O2 . . . . -179.63(16) ?
N1 C3 C4 C5 . . . . -178.40(15) ?
C2 C3 C4 C5 . . . . 1.2(2) ?
O2 C4 C5 C6 . . . . -179.57(16) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C10 N2 C6 C5 . . . . -0.9(3) ?
C10 N2 C6 C1 . . . . 179.18(14) ?
C4 C5 C6 N2 . . . . 179.17(16) ?
C4 C5 C6 C1 . . . . -0.9(2) ?
O1 C1 C6 N2 . . . . 2.2(2) ?
C2 C1 C6 N2 . . . . -178.43(15) ?
O1 C1 C6 C5 . . . . -177.71(15) ?
C2 C1 C6 C5 . . . . 1.7(2) ?
C3 N1 C7 C8 . . . . 83.0(2) ?
N1 C7 C8 C9 . . . . 56.7(2) ?
C7 C8 C9 O3 . . . . 58.3(2) ?
C6 N2 C10 C11 . . . . -126.19(17) ?
N2 C10 C11 C12 . . . . 68.29(17) ?
C10 C11 C12 O4 . . . . -174.07(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656784
