#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029629.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_4029629
loop_
_publ_author_name
'Semakin, Artem N.'
'Sukhorukov, Alexey Yu'
'Nelyubina, Yulia V.'
'Khomutova, Yulia A.'
'Ioffe, Sema L.'
'Tartakovsky, Vladimir A.'
_publ_section_title
;
 Urotropine isomer (1,4,6,10-tetraazaadamantane): synthesis, structure,
 and chemistry.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6079
_journal_page_last               6086
_journal_paper_doi               10.1021/jo5007703
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H19 N4, C H4 O, Br'
_chemical_formula_sum            'C14 H23 Br N4 O'
_chemical_formula_weight         343.27
_chemical_name_systematic
; 
 ? 
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.549(2)
_cell_angle_beta                 65.834(2)
_cell_angle_gamma                75.133(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7493(12)
_cell_length_b                   9.6705(14)
_cell_length_c                   10.0013(14)
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     745.36(18)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8900
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.760
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0287
_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)+(0.0320P)²+0.3925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                3459
_reflns_number_total             3942
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            jo5007703_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029629.cif.
;
_cod_database_code               4029629
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
Br1 Br 0.22075(2) 0.54568(2) 0.29457(2) 0.01670(6) Uani 1 1 d .
C1" C 0.2954(2) 0.65636(19) 0.58064(19) 0.0139(4) Uani 1 1 d .
H1" H 0.3641 0.6541 0.4725 0.017 Uiso 1 1 calc R
C1 C 0.0303(2) 0.7626(2) 0.7663(2) 0.0144(4) Uani 1 1 d .
H1 H -0.0815 0.8327 0.7844 0.017 Uiso 1 1 calc R
C1' C 0.1594(2) 0.5165(2) 0.7945(2) 0.0144(4) Uani 1 1 d .
H1' H 0.1359 0.4193 0.8321 0.017 Uiso 1 1 calc R
C2" C 0.3960(2) 0.7011(2) 0.65325(19) 0.0129(3) Uani 1 1 d .
H2"B H 0.5077 0.6324 0.6325 0.015 Uiso 1 1 calc R
H2"A H 0.4185 0.7972 0.6139 0.015 Uiso 1 1 calc R
C2 C 0.1235(2) 0.80921(19) 0.8456(2) 0.0126(3) Uani 1 1 d .
H2B H 0.1432 0.9066 0.8094 0.015 Uiso 1 1 calc R
H2A H 0.0532 0.8112 0.9523 0.015 Uiso 1 1 calc R
C2' C 0.2583(2) 0.55594(19) 0.8720(2) 0.0136(3) Uani 1 1 d .
H2'B H 0.3683 0.4851 0.8525 0.016 Uiso 1 1 calc R
H2'A H 0.1910 0.5549 0.9793 0.016 Uiso 1 1 calc R
N3 N 0.1358(2) 0.76638(17) 0.60818(17) 0.0151(3) Uani 1 1 d .
H3 H 0.0825 0.7479 0.5640 0.018 Uiso 1 1 d R
N3" N -0.0051(2) 0.62174(17) 0.83067(17) 0.0146(3) Uani 1 1 d .
H3" H -0.0656 0.5937 0.7839 0.018 Uiso 1 1 d R
N3' N 0.2692(2) 0.51131(17) 0.63726(17) 0.0156(3) Uani 1 1 d .
H3' H 0.2224 0.4831 0.5822 0.019 Uiso 1 1 d R
N4 N 0.29281(19) 0.70411(16) 0.81685(16) 0.0108(3) Uani 1 1 d .
C4 C 0.3911(2) 0.73991(19) 0.89718(19) 0.0126(3) Uani 1 1 d .
H4B H 0.3227 0.7332 1.0040 0.015 Uiso 1 1 calc R
H4A H 0.4998 0.6671 0.8763 0.015 Uiso 1 1 calc R
C5 C 0.4325(2) 0.88608(19) 0.85719(19) 0.0125(3) Uani 1 1 d .
C6 C 0.5865(2) 0.9048(2) 0.7431(2) 0.0155(4) Uani 1 1 d .
H6 H 0.6631 0.8257 0.6873 0.019 Uiso 1 1 calc R
C6' C 0.3229(2) 1.0035(2) 0.9384(2) 0.0141(4) Uani 1 1 d .
H6' H 0.2184 0.9919 1.0167 0.017 Uiso 1 1 calc R
C7 C 0.6283(3) 1.0389(2) 0.7108(2) 0.0191(4) Uani 1 1 d .
H7 H 0.7328 1.0512 0.6329 0.023 Uiso 1 1 calc R
C7' C 0.3644(3) 1.1371(2) 0.9064(2) 0.0164(4) Uani 1 1 d .
H7' H 0.2883 1.2163 0.9624 0.020 Uiso 1 1 calc R
C8 C 0.5168(3) 1.1547(2) 0.7929(2) 0.0188(4) Uani 1 1 d .
H8 H 0.5453 1.2461 0.7710 0.023 Uiso 1 1 calc R
O1S O -0.0315(2) 0.82539(18) 0.21991(16) 0.0306(4) Uani 1 1 d .
H1SO H 0.0427 0.7637 0.2326 0.037 Uiso 1 1 d R
C1S C -0.1678(3) 0.8439(2) 0.3596(2) 0.0246(4) Uani 1 1 d .
H1SA H -0.1636 0.7536 0.4186 0.037 Uiso 1 1 calc R
H1SB H -0.2776 0.8720 0.3478 0.037 Uiso 1 1 calc R
H1SC H -0.1565 0.9186 0.4091 0.037 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
N3' C1" N3 114.36(15)
N3' C1" C2" 108.77(15)
N3 C1" C2" 107.42(14)
N3' C1" H1" 108.7
N3 C1" H1" 108.7
C2" C1" H1" 108.7
N3 C1 N3" 115.06(15)
N3 C1 C2 108.22(15)
N3" C1 C2 107.62(15)
N3 C1 H1 108.6
N3" C1 H1 108.6
C2 C1 H1 108.6
N3' C1' N3" 114.64(15)
N3' C1' C2' 107.51(15)
N3" C1' C2' 107.85(15)
N3' C1' H1' 108.9
N3" C1' H1' 108.9
C2' C1' H1' 108.9
N4 C2" C1" 108.83(14)
N4 C2" H2"B 109.9
C1" C2" H2"B 109.9
N4 C2" H2"A 109.9
C1" C2" H2"A 109.9
H2"B C2" H2"A 108.3
N4 C2 C1 108.48(14)
N4 C2 H2B 110.0
C1 C2 H2B 110.0
N4 C2 H2A 110.0
C1 C2 H2A 110.0
H2B C2 H2A 108.4
C1' C2' N4 109.27(14)
C1' C2' H2'B 109.8
N4 C2' H2'B 109.8
C1' C2' H2'A 109.8
N4 C2' H2'A 109.8
H2'B C2' H2'A 108.3
C1 N3 C1" 108.45(14)
C1 N3 H3 108.7
C1" N3 H3 109.3
C1 N3" C1' 108.50(14)
C1 N3" H3" 108.0
C1' N3" H3" 106.4
C1' N3' C1" 108.67(14)
C1' N3' H3' 113.7
C1" N3' H3' 106.3
C2 N4 C2" 108.90(13)
C2 N4 C2' 108.69(14)
C2" N4 C2' 108.18(13)
C2 N4 C4 111.78(13)
C2" N4 C4 111.46(14)
C2' N4 C4 107.72(13)
C5 C4 N4 114.51(14)
C5 C4 H4B 108.6
N4 C4 H4B 108.6
C5 C4 H4A 108.6
N4 C4 H4A 108.6
H4B C4 H4A 107.6
C6' C5 C6 118.75(17)
C6' C5 C4 120.65(16)
C6 C5 C4 120.49(16)
C7 C6 C5 120.41(18)
C7 C6 H6 119.8
C5 C6 H6 119.8
C7' C6' C5 120.90(17)
C7' C6' H6' 119.5
C5 C6' H6' 119.5
C8 C7 C6 119.87(18)
C8 C7 H7 120.1
C6 C7 H7 120.1
C8 C7' C6' 119.92(18)
C8 C7' H7' 120.0
C6' C7' H7' 120.0
C7' C8 C7 120.13(18)
C7' C8 H8 119.9
C7 C8 H8 119.9
C1S O1S H1SO 105.4
O1S C1S H1SA 109.5
O1S C1S H1SB 109.5
H1SA C1S H1SB 109.5
O1S C1S H1SC 109.5
H1SA C1S H1SC 109.5
H1SB C1S H1SC 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1" N3' 1.472(2)
C1" N3 1.472(2)
C1" C2" 1.517(3)
C1" H1" 1.0000
C1 N3 1.469(2)
C1 N3" 1.470(2)
C1 C2 1.523(3)
C1 H1 1.0000
C1' N3' 1.470(2)
C1' N3" 1.472(2)
C1' C2' 1.517(3)
C1' H1' 1.0000
C2" N4 1.511(2)
C2" H2"B 0.9900
C2" H2"A 0.9900
C2 N4 1.508(2)
C2 H2B 0.9900
C2 H2A 0.9900
C2' N4 1.517(2)
C2' H2'B 0.9900
C2' H2'A 0.9900
N3 H3 0.8246
N3" H3" 0.9415
N3' H3' 0.9119
N4 C4 1.518(2)
C4 C5 1.506(2)
C4 H4B 0.9900
C4 H4A 0.9900
C5 C6' 1.394(3)
C5 C6 1.399(3)
C6 C7 1.394(3)
C6 H6 0.9500
C6' C7' 1.388(3)
C6' H6' 0.9500
C7 C8 1.390(3)
C7 H7 0.9500
C7' C8 1.385(3)
C7' H7' 0.9500
C8 H8 0.9500
O1S C1S 1.416(3)
O1S H1SO 0.8000
C1S H1SA 0.9800
C1S H1SB 0.9800
C1S H1SC 0.9800
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
N3' C1" C2" N4 -61.55(18)
N3 C1" C2" N4 62.73(18)
N3 C1 C2 N4 -61.75(18)
N3" C1 C2 N4 63.17(18)
N3' C1' C2' N4 62.80(18)
N3" C1' C2' N4 -61.32(18)
N3" C1 N3 C1" -54.4(2)
C2 C1 N3 C1" 66.03(18)
N3' C1" N3 C1 54.57(19)
C2" C1" N3 C1 -66.24(18)
N3 C1 N3" C1' 54.0(2)
C2 C1 N3" C1' -66.72(17)
N3' C1' N3" C1 -53.96(19)
C2' C1' N3" C1 65.75(18)
N3" C1' N3' C1" 54.6(2)
C2' C1' N3' C1" -65.28(18)
N3 C1" N3' C1' -54.9(2)
C2" C1" N3' C1' 65.18(19)
C1 C2 N4 C2" 58.57(18)
C1 C2 N4 C2' -59.07(17)
C1 C2 N4 C4 -177.84(14)
C1" C2" N4 C2 -59.50(18)
C1" C2" N4 C2' 58.46(18)
C1" C2" N4 C4 176.71(14)
C1' C2' N4 C2 58.48(18)
C1' C2' N4 C2" -59.62(18)
C1' C2' N4 C4 179.77(14)
C2 N4 C4 C5 -59.38(19)
C2" N4 C4 C5 62.75(19)
C2' N4 C4 C5 -178.72(14)
N4 C4 C5 C6' 92.9(2)
N4 C4 C5 C6 -90.8(2)
C6' C5 C6 C7 -0.6(3)
C4 C5 C6 C7 -176.93(17)
C6 C5 C6' C7' 0.6(3)
C4 C5 C6' C7' 176.90(17)
C5 C6 C7 C8 0.3(3)
C5 C6' C7' C8 -0.3(3)
C6' C7' C8 C7 0.0(3)
C6 C7 C8 C7' -0.1(3)
