#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:43:29 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/22/2242207.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_2242207
loop_
_publ_author_name
'Vatsadze, Sergey Z.'
'Manaenkova, Marina A.'
'Vasilev, Evgeny V.'
'Venskovsky, Nikolai U.'
'Khrustalev, Victor N.'
_publ_section_title
;
 Crystal structures and supramolecular features of
 9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone,
 3,7-diazaspiro[bicyclo[3.3.1]nonane-9,1'-cyclopentane]-2,4,6,8-tetraone
 and 9-methyl-9-phenyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone
 dimethylformamide monosolvate
;
_journal_coeditor_code           LD2140
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1097
_journal_page_last               1101
_journal_paper_doi               10.1107/S2056989017009458
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C14 H12 N2 O4, C3 H7 N O'
_chemical_formula_moiety         'C14 H12 N2 O4, C3 H7 N O'
_chemical_formula_sum            'C17 H19 N3 O5'
_chemical_formula_weight         345.35
_chemical_name_systematic
;
9-Methyl-9-phenyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone
dimethylformamide monosolvate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.7876(5)
_cell_length_b                   19.4656(12)
_cell_length_c                   21.7879(13)
_cell_measurement_reflns_used    2856
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.29
_cell_volume                     3302.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41691
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         1.869
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0448P)²+1.1286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                3210
_reflns_number_total             5056
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ld2140sup1.cif
_cod_data_source_block           III
_cod_database_code               2242207
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_occupancy
O O1 0.91018(15) 0.32972(6) 0.24687(5) 0.0195(3) Uani d 1
O O2 1.28067(16) 0.39316(7) 0.39546(6) 0.0277(3) Uani d 1
O O3 1.05101(18) 0.54938(6) 0.41859(6) 0.0284(3) Uani d 1
O O4 0.71389(17) 0.48551(6) 0.25953(6) 0.0247(3) Uani d 1
C C1 0.7904(2) 0.39619(8) 0.33006(7) 0.0154(3) Uani d 1
H H1 0.6777 0.3746 0.3193 0.019 Uiso calc 1
C C2 0.9331(2) 0.35860(8) 0.29593(7) 0.0156(3) Uani d 1
N N3 1.09219(18) 0.36122(7) 0.32247(6) 0.0169(3) Uani d 1
H H3 1.178(2) 0.3463(10) 0.3014(9) 0.020 Uiso d 1
C C4 1.1346(2) 0.39341(9) 0.37714(7) 0.0176(3) Uani d 1
C C5 0.9888(2) 0.42888(8) 0.41126(8) 0.0159(3) Uani d 1
H H5 1.0146 0.4280 0.4562 0.019 Uiso calc 1
C C6 0.9822(2) 0.50346(9) 0.38999(8) 0.0197(4) Uani d 1
N N7 0.89576(19) 0.51620(7) 0.33590(7) 0.0196(3) Uani d 1
H H7 0.902(3) 0.5588(10) 0.3194(9) 0.024 Uiso d 1
C C8 0.7939(2) 0.46953(9) 0.30509(8) 0.0177(3) Uani d 1
C C9 0.8163(2) 0.39217(8) 0.40019(7) 0.0157(3) Uani d 1
C C10 0.8217(2) 0.31744(8) 0.42225(7) 0.0157(3) Uani d 1
C C11 0.7451(2) 0.26429(9) 0.38892(8) 0.0200(4) Uani d 1
H H11 0.6928 0.2740 0.3505 0.024 Uiso calc 1
C C12 0.7444(2) 0.19734(9) 0.41138(8) 0.0229(4) Uani d 1
H H12 0.6912 0.1618 0.3883 0.027 Uiso calc 1
C C13 0.8208(2) 0.18232(9) 0.46704(8) 0.0226(4) Uani d 1
H H13 0.8210 0.1365 0.4821 0.027 Uiso calc 1
C C14 0.8969(2) 0.23430(9) 0.50061(8) 0.0218(4) Uani d 1
H H14 0.9496 0.2242 0.5389 0.026 Uiso calc 1
C C15 0.8965(2) 0.30139(9) 0.47846(8) 0.0196(4) Uani d 1
H H15 0.9482 0.3368 0.5021 0.024 Uiso calc 1
C C16 0.6721(2) 0.43004(9) 0.43480(8) 0.0205(4) Uani d 1
H H16A 0.6658 0.4777 0.4205 0.031 Uiso calc 1
H H16B 0.6965 0.4295 0.4789 0.031 Uiso calc 1
H H16C 0.5623 0.4071 0.4270 0.031 Uiso calc 1
O O5 0.91561(18) 0.64557(7) 0.28362(6) 0.0289(3) Uani d 1
N N1 0.84929(19) 0.65410(7) 0.18198(7) 0.0212(3) Uani d 1
C C17 0.8439(2) 0.67440(9) 0.24001(8) 0.0232(4) Uani d 1
H H17 0.7793 0.7146 0.2489 0.028 Uiso calc 1
C C18 0.9381(3) 0.59137(10) 0.16458(9) 0.0284(4) Uani d 1
H H18A 1.0181 0.5782 0.1972 0.043 Uiso calc 1
H H18B 1.0020 0.5991 0.1265 0.043 Uiso calc 1
H H18C 0.8541 0.5545 0.1583 0.043 Uiso calc 1
C C19 0.7595(3) 0.69190(10) 0.13395(9) 0.0273(4) Uani d 1
H H19A 0.6956 0.7301 0.1523 0.041 Uiso calc 1
H H19B 0.6795 0.6611 0.1128 0.041 Uiso calc 1
H H19C 0.8431 0.7099 0.1044 0.041 Uiso calc 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 C8 105.18(13)
C2 C1 C9 111.30(13)
C8 C1 C9 113.43(13)
C2 C1 H1 108.9
C8 C1 H1 108.9
C9 C1 H1 108.9
O1 C2 N3 121.31(15)
O1 C2 C1 122.78(15)
N3 C2 C1 115.87(14)
C2 N3 C4 126.58(15)
C2 N3 H3 117.7(13)
C4 N3 H3 115.2(13)
O2 C4 N3 120.51(16)
O2 C4 C5 122.95(15)
N3 C4 C5 116.53(14)
C4 C5 C6 107.97(14)
C4 C5 C9 111.32(13)
C6 C5 C9 111.39(14)
C4 C5 H5 108.7
C6 C5 H5 108.7
C9 C5 H5 108.7
O3 C6 N7 121.43(16)
O3 C6 C5 122.02(15)
N7 C6 C5 116.55(15)
C6 N7 C8 125.29(15)
C6 N7 H7 118.5(13)
C8 N7 H7 116.2(13)
O4 C8 N7 121.65(16)
O4 C8 C1 121.45(15)
N7 C8 C1 116.88(14)
C10 C9 C16 108.70(13)
C10 C9 C5 111.53(13)
C16 C9 C5 109.69(13)
C10 C9 C1 111.25(13)
C16 C9 C1 111.43(13)
C5 C9 C1 104.20(13)
C15 C10 C11 118.01(15)
C15 C10 C9 120.04(14)
C11 C10 C9 121.86(14)
C12 C11 C10 120.78(16)
C12 C11 H11 119.6
C10 C11 H11 119.6
C13 C12 C11 120.33(17)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 119.61(17)
C12 C13 H13 120.2
C14 C13 H13 120.2
C13 C14 C15 120.16(17)
C13 C14 H14 119.9
C15 C14 H14 119.9
C10 C15 C14 121.10(16)
C10 C15 H15 119.5
C14 C15 H15 119.5
C9 C16 H16A 109.5
C9 C16 H16B 109.5
H16A C16 H16B 109.5
C9 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C17 N1 C18 120.96(15)
C17 N1 C19 121.26(15)
C18 N1 C19 117.71(15)
O5 C17 N1 125.66(17)
O5 C17 H17 117.2
N1 C17 H17 117.2
N1 C18 H18A 109.5
N1 C18 H18B 109.5
H18A C18 H18B 109.5
N1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
N1 C19 H19A 109.5
N1 C19 H19B 109.5
H19A C19 H19B 109.5
N1 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2209(19)
O2 C4 1.205(2)
O3 C6 1.214(2)
O4 C8 1.213(2)
C1 C2 1.524(2)
C1 C8 1.528(2)
C1 C9 1.543(2)
C1 H1 1.0000
C2 N3 1.368(2)
N3 C4 1.386(2)
N3 H3 0.861(19)
C4 C5 1.523(2)
C5 C6 1.525(2)
C5 C9 1.541(2)
C5 H5 1.0000
C6 N7 1.380(2)
N7 C8 1.380(2)
N7 H7 0.90(2)
C9 C10 1.533(2)
C9 C16 1.540(2)
C10 C15 1.392(2)
C10 C11 1.398(2)
C11 C12 1.392(2)
C11 H11 0.9500
C12 C13 1.382(3)
C12 H12 0.9500
C13 C14 1.382(2)
C13 H13 0.9500
C14 C15 1.392(2)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
O5 C17 1.237(2)
N1 C17 1.325(2)
N1 C18 1.454(2)
N1 C19 1.458(2)
C17 H17 0.9500
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
N3 H3 O1 6_656 0.861(19) 2.12(2) 2.9650(19) 168.3(18)
N7 H7 O5 . 0.90(2) 1.86(2) 2.7682(19) 178.6(18)
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
C8 C1 C2 O1 -88.55(18)
C9 C1 C2 O1 148.23(15)
C8 C1 C2 N3 89.02(16)
C9 C1 C2 N3 -34.20(19)
O1 C2 N3 C4 178.71(15)
C1 C2 N3 C4 1.1(2)
C2 N3 C4 O2 -178.77(16)
C2 N3 C4 C5 0.6(2)
O2 C4 C5 C6 87.7(2)
N3 C4 C5 C6 -91.58(17)
O2 C4 C5 C9 -149.71(16)
N3 C4 C5 C9 31.0(2)
C4 C5 C6 O3 -96.53(19)
C9 C5 C6 O3 140.95(17)
C4 C5 C6 N7 82.61(18)
C9 C5 C6 N7 -39.9(2)
O3 C6 N7 C8 -170.25(17)
C5 C6 N7 C8 10.6(2)
C6 N7 C8 O4 175.77(16)
C6 N7 C8 C1 -5.8(2)
C2 C1 C8 O4 87.35(18)
C9 C1 C8 O4 -150.80(15)
C2 C1 C8 N7 -91.04(16)
C9 C1 C8 N7 30.8(2)
C4 C5 C9 C10 60.15(17)
C6 C5 C9 C10 -179.28(13)
C4 C5 C9 C16 -179.36(13)
C6 C5 C9 C16 -58.79(18)
C4 C5 C9 C1 -59.96(16)
C6 C5 C9 C1 60.61(16)
C2 C1 C9 C10 -58.45(17)
C8 C1 C9 C10 -176.82(13)
C2 C1 C9 C16 -179.93(13)
C8 C1 C9 C16 61.69(18)
C2 C1 C9 C5 61.86(16)
C8 C1 C9 C5 -56.52(17)
C16 C9 C10 C15 -77.40(18)
C5 C9 C10 C15 43.7(2)
C1 C9 C10 C15 159.54(15)
C16 C9 C10 C11 99.18(17)
C5 C9 C10 C11 -139.75(16)
C1 C9 C10 C11 -23.9(2)
C15 C10 C11 C12 -0.2(2)
C9 C10 C11 C12 -176.84(16)
C10 C11 C12 C13 -0.4(3)
C11 C12 C13 C14 0.5(3)
C12 C13 C14 C15 0.0(3)
C11 C10 C15 C14 0.7(2)
C9 C10 C15 C14 177.42(15)
C13 C14 C15 C10 -0.6(3)
C18 N1 C17 O5 3.0(3)
C19 N1 C17 O5 179.89(18)

_cod_database_fobs_code 2242207
