#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152877.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7152877
loop_
_publ_author_name
'Rowley, Julian H.'
'Yau, Sze Chak'
'Kariuki, Benson M.'
'Kennedy, Alan R.'
'Tomkinson, Nicholas C. O.'
_publ_section_title
;
 Readily accessible chiral at nitrogen cage structures.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2198
_journal_page_last               2205
_journal_paper_doi               10.1039/c3ob27458f
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H20 N4 O2'
_chemical_formula_sum            'C11 H20 N4 O2'
_chemical_formula_weight         240.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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            4
_cell_length_a                   7.9849(3)
_cell_length_b                   7.9849(3)
_cell_length_c                   19.6071(8)
_cell_measurement_reflns_used    1261
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.76
_cell_volume                     1250.12(8)
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXs-97
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD 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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2349
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Denzo/scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       0.112(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1261
_reflns_number_total             1446
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob27458f.txt
_cod_data_source_block           nct0910
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P43212
_cod_database_code               7152877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/4'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'y+1/2, -x+1/2, z+1/4'
'-y+1/2, x+1/2, z+3/4'
'-y, -x, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H3 H 0.7101(19) 0.6056(19) 0.0279(8) 0.019(4) Uiso 1 1 d .
C1 C 0.41588(19) 0.3017(2) 0.07628(8) 0.0269(4) Uani 1 1 d .
C2 C 0.63805(19) 0.30683(19) -0.01292(8) 0.0269(4) Uani 1 1 d .
H2A H 0.7285 0.3225 0.0210 0.032 Uiso 1 1 calc R
H2B H 0.6793 0.2258 -0.0473 0.032 Uiso 1 1 calc R
C3 C 0.60550(19) 0.60550(19) 0.0000 0.0270(5) Uani 1 2 d S
C4 C 0.4696(2) 0.47906(19) 0.09921(7) 0.0269(4) Uani 1 1 d .
H4 H 0.5887 0.4701 0.1146 0.032 Uiso 1 1 calc R
C5 C 0.3682(3) 0.5318(2) 0.16122(9) 0.0416(5) Uani 1 1 d .
H5A H 0.3993 0.6460 0.1744 0.062 Uiso 1 1 calc R
H5B H 0.3914 0.4552 0.1991 0.062 Uiso 1 1 calc R
H5C H 0.2486 0.5281 0.1501 0.062 Uiso 1 1 calc R
C6 C 0.4383(2) 0.0644(2) 0.00140(10) 0.0381(5) Uani 1 1 d .
H6A H 0.4703 -0.0174 0.0363 0.057 Uiso 1 1 calc R
H6B H 0.4910 0.0347 -0.0421 0.057 Uiso 1 1 calc R
H6C H 0.3162 0.0642 -0.0040 0.057 Uiso 1 1 calc R
N1 N 0.49370(15) 0.23087(15) 0.02215(6) 0.0265(4) Uani 1 1 d .
N2 N 0.46494(15) 0.61070(15) 0.04679(7) 0.0248(3) Uani 1 1 d .
O1 O 0.30428(16) 0.22696(16) 0.10702(6) 0.0401(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0280(8) 0.0264(8) 0.0265(8) 0.0058(6) -0.0016(6) -0.0012(6)
C2 0.0249(7) 0.0279(8) 0.0279(8) -0.0016(6) 0.0008(6) 0.0037(6)
C3 0.0250(7) 0.0250(7) 0.0310(12) -0.0003(7) 0.0003(7) -0.0038(9)
C4 0.0276(8) 0.0289(8) 0.0244(8) -0.0009(6) -0.0028(6) -0.0001(7)
C5 0.0528(11) 0.0454(11) 0.0265(8) -0.0031(8) 0.0021(8) 0.0046(9)
C6 0.0476(10) 0.0217(8) 0.0449(10) -0.0024(8) -0.0074(9) -0.0041(7)
N1 0.0306(7) 0.0204(7) 0.0286(7) 0.0004(5) -0.0015(6) -0.0017(5)
N2 0.0241(7) 0.0219(6) 0.0284(7) -0.0015(5) -0.0022(5) -0.0001(5)
O1 0.0410(7) 0.0400(8) 0.0393(7) 0.0090(6) 0.0068(6) -0.0104(6)
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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 N1 120.92(15) . .
O1 C1 C4 120.17(14) . .
N1 C1 C4 118.91(13) . .
N2 C2 N1 117.17(13) 5 .
N2 C2 H2A 108.0 5 .
N1 C2 H2A 108.0 . .
N2 C2 H2B 108.0 5 .
N1 C2 H2B 108.0 . .
H2A C2 H2B 107.2 . .
N2 C3 N2 116.39(17) . 5
N2 C3 H3 107.5(9) . .
N2 C3 H3 108.9(9) 5 .
N2 C4 C5 110.35(13) . .
N2 C4 C1 116.38(12) . .
C5 C4 C1 109.80(13) . .
N2 C4 H4 106.6 . .
C5 C4 H4 106.6 . .
C1 C4 H4 106.6 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 H6A 109.5 . .
N1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C1 N1 C6 117.40(13) . .
C1 N1 C2 123.58(12) . .
C6 N1 C2 118.85(13) . .
C2 N2 C3 112.98(11) 5 .
C2 N2 C4 116.85(12) 5 .
C3 N2 C4 113.72(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2304(18) .
C1 N1 1.354(2) .
C1 C4 1.546(2) .
C2 N2 1.4430(19) 5
C2 N1 1.4728(19) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N2 1.4501(17) .
C3 N2 1.4501(17) 5
C3 H3 0.999(16) .
C4 N2 1.4707(19) .
C4 C5 1.520(2) .
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 N1 1.4586(19) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
N2 C2 1.4430(19) 5
