#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/57/7105733.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_7105733
loop_
_publ_author_name
'Gorakh Yellol'
'Tsai-Wen Chung'
'Chung-Ming Sun'
_publ_section_title
;
 Novel Cyclization of Bis-Boc-Guanidines: Expeditive Traceless Synthesis
 of 1,3,5-Oxadiazinones under Microwave Conditions
;
_journal_name_full               Chem.Commun.
_journal_page_first              9170
_journal_paper_doi               10.1039/c0cc03519j
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C12 H16 N6 O2'
_chemical_formula_sum            'C12 H16 N6 O2'
_chemical_formula_weight         276.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                82.0870(10)
_cell_angle_beta                 73.1960(10)
_cell_angle_gamma                79.414(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3983(6)
_cell_length_b                   8.0111(6)
_cell_length_c                   11.8143(9)
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.003
_cell_measurement_theta_min      2.596
_cell_volume                     656.24(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3742
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.61
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.067(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.397
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.397
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1925
_refine_ls_wR_factor_ref         0.2033
_reflns_number_gt                2185
_reflns_number_total             2530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03519J.TXT
_cod_data_source_block           cnbr16m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constro' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               7105733
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21812(15) 0.92328(13) 0.61404(9) 0.0384(4) Uani 1 1 d . . .
O2 O 0.17988(19) 0.72326(14) 0.51572(10) 0.0513(4) Uani 1 1 d . . .
N1 N 0.27901(19) 1.11437(17) 0.71272(11) 0.0378(4) Uani 1 1 d . . .
N2 N 0.23309(19) 0.97829(16) 0.40895(11) 0.0366(4) Uani 1 1 d . . .
N3 N 0.30265(18) 1.18456(16) 0.51430(11) 0.0362(4) Uani 1 1 d . . .
N4 N 0.2949(2) 1.24320(17) 0.32046(11) 0.0411(4) Uani 1 1 d . . .
N5 N 0.1183(2) 1.51826(18) 0.19395(12) 0.0444(4) Uani 1 1 d . . .
N6 N 0.2762(3) 1.6580(3) 0.00017(16) 0.0797(7) Uani 1 1 d . . .
C1 C 0.3469(2) 1.2693(2) 0.72656(13) 0.0407(4) Uani 1 1 d . . .
H1A H 0.2524 1.3695 0.7216 0.049 Uiso 1 1 calc R . .
H1B H 0.4656 1.2851 0.6671 0.049 Uiso 1 1 calc R . .
C2 C 0.3756(5) 1.2335(3) 0.84899(18) 0.0848(9) Uani 1 1 d . . .
H2B H 0.5096 1.1947 0.8439 0.102 Uiso 1 1 calc R . .
H2C H 0.3352 1.3364 0.8901 0.102 Uiso 1 1 calc R . .
C3 C 0.2626(4) 1.1023(3) 0.91303(16) 0.0704(7) Uani 1 1 d . . .
H3B H 0.1393 1.1541 0.9598 0.085 Uiso 1 1 calc R . .
H3C H 0.3277 1.0290 0.9661 0.085 Uiso 1 1 calc R . .
C4 C 0.2367(3) 1.0007(2) 0.82253(14) 0.0473(5) Uani 1 1 d . . .
H4A H 0.3249 0.8945 0.8156 0.057 Uiso 1 1 calc R . .
H4B H 0.1071 0.9760 0.8427 0.057 Uiso 1 1 calc R . .
C5 C 0.2681(2) 1.07738(19) 0.60950(13) 0.0325(4) Uani 1 1 d . . .
C6 C 0.2097(2) 0.86783(19) 0.50573(13) 0.0360(4) Uani 1 1 d . . .
C7 C 0.2745(2) 1.13069(19) 0.41764(12) 0.0335(4) Uani 1 1 d . . .
C8 C 0.2461(3) 1.2131(2) 0.21430(14) 0.0439(5) Uani 1 1 d . . .
H8A H 0.2131 1.0994 0.2232 0.053 Uiso 1 1 calc R . .
H8B H 0.3553 1.2211 0.1456 0.053 Uiso 1 1 calc R . .
C9 C 0.0788(3) 1.3441(2) 0.19608(14) 0.0438(4) Uani 1 1 d . . .
H9A H 0.0544 1.3305 0.1218 0.053 Uiso 1 1 calc R . .
H9B H -0.0345 1.3258 0.2598 0.053 Uiso 1 1 calc R . .
C10 C 0.1699(3) 1.5463(2) 0.30090(14) 0.0473(5) Uani 1 1 d . . .
H10A H 0.0609 1.5386 0.3698 0.057 Uiso 1 1 calc R . .
H10B H 0.2035 1.6597 0.2923 0.057 Uiso 1 1 calc R . .
C11 C 0.3370(3) 1.4149(2) 0.31946(14) 0.0458(5) Uani 1 1 d . . .
H11A H 0.4510 1.4328 0.2562 0.055 Uiso 1 1 calc R . .
H11B H 0.3607 1.4274 0.3942 0.055 Uiso 1 1 calc R . .
C12 C 0.2074(3) 1.5910(2) 0.09041(15) 0.0487(5) Uani 1 1 d . . .
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
_geom_angle_publ_flag
C5 O1 C6 117.82(11) . . ?
C5 N1 C1 122.77(13) . . ?
C5 N1 C4 123.71(14) . . ?
C1 N1 C4 113.41(12) . . ?
C6 N2 C7 117.69(13) . . ?
C5 N3 C7 114.00(13) . . ?
C7 N4 C8 122.16(13) . . ?
C7 N4 C11 122.75(13) . . ?
C8 N4 C11 114.38(12) . . ?
C12 N5 C9 117.25(14) . . ?
C12 N5 C10 118.30(14) . . ?
C9 N5 C10 112.98(12) . . ?
N1 C1 C2 102.30(13) . . ?
N1 C1 H1A 111.3 . . ?
C2 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
C2 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
C3 C2 C1 108.08(17) . . ?
C3 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C3 C2 H2C 110.1 . . ?
C1 C2 H2C 110.1 . . ?
H2B C2 H2C 108.4 . . ?
C2 C3 C4 107.44(16) . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C2 C3 H3C 110.2 . . ?
C4 C3 H3C 110.2 . . ?
H3B C3 H3C 108.5 . . ?
N1 C4 C3 102.94(14) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N3 C5 N1 121.62(14) . . ?
N3 C5 O1 125.04(13) . . ?
N1 C5 O1 113.34(13) . . ?
O2 C6 N2 128.32(14) . . ?
O2 C6 O1 113.44(13) . . ?
N2 C6 O1 118.24(12) . . ?
N2 C7 N4 117.64(13) . . ?
N2 C7 N3 126.75(13) . . ?
N4 C7 N3 115.60(13) . . ?
N4 C8 C9 109.69(14) . . ?
N4 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N4 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N5 C9 C8 110.80(13) . . ?
N5 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N5 C10 C11 110.63(14) . . ?
N5 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C10 109.88(13) . . ?
N4 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N4 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N6 C12 N5 176.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3422(18) . ?
O1 C6 1.4324(17) . ?
O2 C6 1.2020(18) . ?
N1 C5 1.3216(19) . ?
N1 C1 1.4668(19) . ?
N1 C4 1.4678(19) . ?
N2 C6 1.3355(19) . ?
N2 C7 1.3361(19) . ?
N3 C5 1.3101(18) . ?
N3 C7 1.3563(18) . ?
N4 C7 1.3484(19) . ?
N4 C8 1.4623(19) . ?
N4 C11 1.4631(19) . ?
N5 C12 1.323(2) . ?
N5 C9 1.473(2) . ?
N5 C10 1.477(2) . ?
N6 C12 1.146(2) . ?
C1 C2 1.504(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.454(3) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 C4 1.502(2) . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653233
