#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211715.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_2211715
loop_
_publ_author_name
'Hai-Ling Xi'
'Meng Gao'
'Li-Ping Cao'
'Yi-Tao Li'
_publ_section_title
2,3-Bis(hydroxymethyl)-6-isopropylperhydro-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-1,4-dione
_journal_coeditor_code           AT2193
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o400
_journal_page_last               o401
_journal_paper_doi               10.1107/S1600536806054882
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H19 N5 O4'
_chemical_formula_moiety         'C11 H19 N5 O4'
_chemical_formula_sum            'C11 H19 N5 O4'
_chemical_formula_weight         285.31
_chemical_name_systematic
;
2,3-Bis(hydroxymethyl)-6-(isopropyl)perhydro-2,3,4a,6,7a-
pentaazacyclopenta[cd]indene-1,4-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_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            8
_cell_length_a                   12.778(3)
_cell_length_b                   12.655(3)
_cell_length_c                   15.926(4)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      18.74
_cell_measurement_theta_min      2.56
_cell_volume                     2575.3(11)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1427
_diffrn_reflns_av_sigmaI/netI    0.1160
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28542
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0575
_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)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1428
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2193.cif
_cod_data_source_block           I
_cod_original_cell_volume        2575.2(11)
_cod_database_code               2211715
_cod_database_fobs_code          2211715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
C C1 1.01645(19) 0.5807(2) 0.09324(18) 0.0547(7) Uani d . 1
H H1A 0.9447 0.5654 0.0801 0.082 Uiso calc R 1
H H1B 1.0540 0.5958 0.0424 0.082 Uiso calc R 1
H H1C 1.0196 0.6409 0.1299 0.082 Uiso calc R 1
C C2 1.18386(19) 0.4952(2) 0.13349(16) 0.0575(8) Uani d . 1
H H2A 1.2055 0.5548 0.1665 0.086 Uiso calc R 1
H H2B 1.2056 0.5050 0.0763 0.086 Uiso calc R 1
H H2C 1.2153 0.4321 0.1555 0.086 Uiso calc R 1
C C3 1.06598(18) 0.48508(17) 0.13691(14) 0.0386(6) Uani d . 1
H H3 1.0452 0.4209 0.1068 0.046 Uiso calc R 1
C C4 0.91856(19) 0.48531(18) 0.23833(15) 0.0465(7) Uani d . 1
H H4A 0.8934 0.5479 0.2096 0.056 Uiso calc R 1
H H4B 0.9048 0.4943 0.2978 0.056 Uiso calc R 1
C C5 1.06524(18) 0.37926(19) 0.26598(14) 0.0438(6) Uani d . 1
H H5A 1.0548 0.3859 0.3261 0.053 Uiso calc R 1
H H5B 1.1397 0.3705 0.2562 0.053 Uiso calc R 1
C C6 0.80517(17) 0.3876(2) 0.13475(15) 0.0391(6) Uani d . 1
C C7 1.0459(2) 0.22792(18) 0.16873(15) 0.0377(6) Uani d . 1
C C8 0.89722(17) 0.29062(17) 0.23534(14) 0.0395(6) Uani d . 1
H H8 0.8668 0.2703 0.2895 0.047 Uiso calc R 1
C C9 0.86278(18) 0.21564(17) 0.16448(14) 0.0404(6) Uani d . 1
H H9 0.8243 0.1544 0.1861 0.048 Uiso calc R 1
C C10 0.7275(2) 0.2451(2) 0.04964(17) 0.0577(7) Uani d . 1
H H10A 0.7020 0.1754 0.0649 0.069 Uiso calc R 1
H H10B 0.6677 0.2920 0.0453 0.069 Uiso calc R 1
C C11 0.9724(2) 0.1086(2) 0.06053(16) 0.0524(7) Uani d . 1
H H11A 1.0360 0.0682 0.0691 0.063 Uiso calc R 1
H H11B 0.9139 0.0599 0.0632 0.063 Uiso calc R 1
N N1 1.03086(14) 0.47639(15) 0.22556(11) 0.0401(5) Uani d . 1
N N2 0.86041(14) 0.39350(14) 0.20796(11) 0.0377(5) Uani d . 1
N N3 1.01064(14) 0.28447(15) 0.23645(12) 0.0371(5) Uani d . 1
N N4 0.79719(14) 0.28289(15) 0.11317(12) 0.0424(5) Uani d . 1
N N5 0.96231(15) 0.18518(15) 0.12720(12) 0.0401(5) Uani d . 1
O O1 0.76617(12) 0.46158(14) 0.09727(11) 0.0533(5) Uani d . 1
O O2 1.13844(12) 0.21494(12) 0.15089(10) 0.0511(5) Uani d . 1
O O3 0.77955(14) 0.23978(17) -0.02884(11) 0.0691(6) Uani d . 1
H H3A 0.7394 0.2582 -0.0662 0.104 Uiso calc R 1
O O4 0.97538(14) 0.15480(16) -0.01967(11) 0.0632(6) Uani d . 1
H H4 0.9186 0.1821 -0.0300 0.095 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'
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
C3 C1 H1A 109.5 ?
C3 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C3 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C3 C2 H2A 109.5 ?
C3 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
C3 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
N1 C3 C2 109.95(18) ?
N1 C3 C1 111.41(19) ?
C2 C3 C1 109.16(19) ?
N1 C3 H3 108.8 ?
C2 C3 H3 108.8 ?
C1 C3 H3 108.8 ?
N1 C4 N2 113.19(18) ?
N1 C4 H4A 108.9 ?
N2 C4 H4A 108.9 ?
N1 C4 H4B 108.9 ?
N2 C4 H4B 108.9 ?
H4A C4 H4B 107.8 ?
N1 C5 N3 113.94(18) ?
N1 C5 H5A 108.8 ?
N3 C5 H5A 108.8 ?
N1 C5 H5B 108.8 ?
N3 C5 H5B 108.8 ?
H5A C5 H5B 107.7 ?
O1 C6 N2 126.1(2) ?
O1 C6 N4 126.1(2) ?
N2 C6 N4 107.7(2) yes
O2 C7 N5 126.0(2) ?
O2 C7 N3 124.6(2) ?
N5 C7 N3 109.3(2) yes
N2 C8 N3 112.04(18) ?
N2 C8 C9 103.90(18) ?
N3 C8 C9 105.15(18) ?
N2 C8 H8 111.8 ?
N3 C8 H8 111.8 ?
C9 C8 H8 111.8 ?
N4 C9 N5 115.56(19) ?
N4 C9 C8 102.54(17) ?
N5 C9 C8 102.27(18) ?
N4 C9 H9 111.9 ?
N5 C9 H9 111.9 ?
C8 C9 H9 111.9 ?
O3 C10 N4 110.3(2) ?
O3 C10 H10A 109.6 ?
N4 C10 H10A 109.6 ?
O3 C10 H10B 109.6 ?
N4 C10 H10B 109.6 ?
H10A C10 H10B 108.1 ?
O4 C11 N5 113.1(2) ?
O4 C11 H11A 109.0 ?
N5 C11 H11A 109.0 ?
O4 C11 H11B 109.0 ?
N5 C11 H11B 109.0 ?
H11A C11 H11B 107.8 ?
C4 N1 C5 107.56(18) ?
C4 N1 C3 115.17(18) ?
C5 N1 C3 113.06(18) ?
C6 N2 C8 112.04(19) ?
C6 N2 C4 126.1(2) ?
C8 N2 C4 116.68(19) ?
C7 N3 C8 110.27(18) ?
C7 N3 C5 121.59(19) ?
C8 N3 C5 115.81(18) ?
C6 N4 C10 123.1(2) ?
C6 N4 C9 112.54(19) ?
C10 N4 C9 124.3(2) ?
C7 N5 C11 123.5(2) ?
C7 N5 C9 112.35(19) ?
C11 N5 C9 123.8(2) ?
C10 O3 H3A 109.5 ?
C11 O4 H4 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 1.533(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.513(3) ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 N1 1.486(3) yes
C3 H3 0.9800 ?
C4 N1 1.454(3) yes
C4 N2 1.461(3) yes
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 N1 1.455(3) ?
C5 N3 1.465(3) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 O1 1.217(3) ?
C6 N2 1.365(3) yes
C6 N4 1.373(3) yes
C7 O2 1.228(2) ?
C7 N5 1.367(3) yes
C7 N3 1.370(3) yes
C8 N2 1.451(3) yes
C8 N3 1.452(3) yes
C8 C9 1.539(3) ?
C8 H8 0.9800 ?
C9 N4 1.447(3) ?
C9 N5 1.455(3) ?
C9 H9 0.9800 ?
C10 O3 1.418(3) ?
C10 N4 1.431(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 O4 1.405(3) ?
C11 N5 1.444(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
O3 H3A 0.8200 ?
O4 H4 0.8200 ?
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
C5 H5B O2 . 0.97 2.59 2.925(3) 100.7
O4 H4 O3 . 0.82 1.92 2.728(3) 167.5
C10 H10B O4 4_455 0.97 2.58 3.494(3) 157.0
O3 H3A O2 4_455 0.82 1.90 2.713(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
N2 C8 C9 N4 -8.6(2)
N3 C8 C9 N4 -126.46(17)
N2 C8 C9 N5 111.47(18)
N3 C8 C9 N5 -6.4(2)
N2 C4 N1 C5 -56.0(2)
N2 C4 N1 C3 71.1(3)
N3 C5 N1 C4 56.3(2)
N3 C5 N1 C3 -72.0(2)
C2 C3 N1 C4 169.44(19)
C1 C3 N1 C4 48.3(2)
C2 C3 N1 C5 -66.3(2)
C1 C3 N1 C5 172.50(18)
O1 C6 N2 C8 -179.3(2)
N4 C6 N2 C8 3.6(2)
O1 C6 N2 C4 -25.9(4)
N4 C6 N2 C4 157.0(2)
N3 C8 N2 C6 116.5(2)
C9 C8 N2 C6 3.5(2)
N3 C8 N2 C4 -39.7(3)
C9 C8 N2 C4 -152.66(18)
N1 C4 N2 C6 -102.0(2)
N1 C4 N2 C8 50.3(3)
O2 C7 N3 C8 175.7(2)
N5 C7 N3 C8 -6.9(2)
O2 C7 N3 C5 35.2(3)
N5 C7 N3 C5 -147.45(19)
N2 C8 N3 C7 -103.9(2)
C9 C8 N3 C7 8.3(2)
N2 C8 N3 C5 39.1(3)
C9 C8 N3 C5 151.36(18)
N1 C5 N3 C7 88.5(3)
N1 C5 N3 C8 -50.0(3)
O1 C6 N4 C10 -9.9(4)
N2 C6 N4 C10 167.19(19)
O1 C6 N4 C9 173.0(2)
N2 C6 N4 C9 -9.9(3)
O3 C10 N4 C6 93.0(3)
O3 C10 N4 C9 -90.2(3)
N5 C9 N4 C6 -98.8(2)
C8 C9 N4 C6 11.6(2)
N5 C9 N4 C10 84.2(3)
C8 C9 N4 C10 -165.5(2)
O2 C7 N5 C11 6.7(3)
N3 C7 N5 C11 -170.57(19)
O2 C7 N5 C9 179.7(2)
N3 C7 N5 C9 2.4(2)
O4 C11 N5 C7 -92.8(3)
O4 C11 N5 C9 95.0(3)
N4 C9 N5 C7 113.2(2)
C8 C9 N5 C7 2.7(2)
N4 C9 N5 C11 -73.8(3)
C8 C9 N5 C11 175.65(19)
