#------------------------------------------------------------------------------
#$Date: 2015-12-09 17:43:41 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171343 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/46/7154684.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_7154684
loop_
_publ_author_name
'Thomann, A.'
'Zapp, J.'
'Hutter, M.'
'Empting, M.'
'Hartmann, R. W.'
_publ_section_title
;
 Steering the azido-tetrazole equilibrium of 4-azidopyrimidines via
 substituent variation - implications for drug design and azide-alkyne
 cycloadditions.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10620
_journal_page_last               10630
_journal_paper_doi               10.1039/c5ob01006c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C4 H3 N5 O'
_chemical_formula_sum            'C4 H3 N5 O'
_chemical_formula_weight         137.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-05-18 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1418(10)
_cell_length_b                   5.9625(5)
_cell_length_c                   6.7680(6)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    132(2)
_cell_measurement_theta_max      30.80
_cell_measurement_theta_min      3.10
_cell_volume                     530.33(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      132(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6832
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.179
_diffrn_reflns_theta_min         3.100
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BrukerAXS 2010'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         1096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0429
_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)+(0.0531P)²+0.0931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                803
_reflns_number_total             1096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ob01006c2.cif
_cod_data_source_block           sh3503
_cod_depositor_comments
'Adding full bibliography for 7154682--7154684.cif.'
_cod_database_code               7154684
_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   0.948
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014/6
_shelx_res_file
; 
TITL sh3503a in Pnma 
CELL  0.71073  13.1418   5.9625   6.7680   90.000   90.000   90.000 
ZERR    4.00   0.00100   0.00050   0.00060   0.0000   0.0000   0.0000 
LATT 1 
SYMM 1/2-X, -Y, 1/2+Z 
SYMM -X, 1/2+Y, -Z 
SYMM 1/2+X, 1/2-Y, 1/2-Z 
SFAC C  H  N  O 
UNIT 16  12  20  4 
L.S. 10 
BOND $H 
FMAP 2 
PLAN -5 
ACTA 
SIZE 0.054 0.218 0.398 
TEMP -140.500 
WGHT    0.053100    0.093100 
FVAR       0.51402 
N1    3    1.024464    0.250000    0.286509    10.50000    0.01598    0.02240 = 
         0.01809    0.00000   -0.00045    0.00000 
N2    3    0.896480    0.250000    0.059286    10.50000    0.01807    0.01928 = 
         0.01073    0.00000    0.00222    0.00000 
N3    3    0.852119    0.250000   -0.122181    10.50000    0.02590    0.02808 = 
         0.01333    0.00000   -0.00207    0.00000 
N4    3    0.755381    0.250000   -0.089278    10.50000    0.02476    0.02929 = 
         0.01910    0.00000   -0.00463    0.00000 
N5    3    0.734228    0.250000    0.108939    10.50000    0.01722    0.02707 = 
         0.01931    0.00000   -0.00162    0.00000 
O1    4    1.062796    0.250000   -0.044370    10.50000    0.02365    0.02992 = 
         0.02354    0.00000    0.01169    0.00000 
C1    1    1.002622    0.250000    0.090759    10.50000    0.01697    0.01675 = 
         0.01772    0.00000    0.00319    0.00000 
C2    1    0.823190    0.250000    0.199754    10.50000    0.01692    0.01666 = 
         0.01389    0.00000    0.00230    0.00000 
C3    1    0.852667    0.250000    0.401838    10.50000    0.01959    0.02113 = 
         0.01233    0.00000    0.00159    0.00000 
C4    1    0.953520    0.250000    0.436342    10.50000    0.02163    0.01774 = 
         0.01336    0.00000   -0.00032    0.00000 
H1    2    0.800862    0.250000    0.504780    10.50000    0.02215 
H2    2    0.977963    0.250000    0.570451    10.50000    0.02440 
H3    2    1.090219    0.250000    0.322440    10.50000    0.03346 
HKLF 4 1 0 0 1 1 0 0 0 1 0 
  
REM  sh3503a in Pnma 
REM R1 =  0.0429 for     803 Fo > 4sig(Fo)  and  0.0674 for all    1096 data 
REM     70 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0530      0.0923 
  
REM Highest difference peak  0.483,  deepest hole -0.227,  1-sigma level  0.066 
Q1    1   0.8347  0.2500  0.3116  10.50000  0.05    0.48 
Q2    1   0.9008  0.2500  0.4380  10.50000  0.05    0.46 
Q3    1   1.0090  0.2500  0.2032  10.50000  0.05    0.43 
Q4    1   0.9547  0.2500  0.0709  10.50000  0.05    0.43 
Q5    1   0.7777  0.2500  0.1577  10.50000  0.05    0.42 
;
_shelx_res_checksum              49935
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 1.02446(10) 0.2500 0.2865(2) 0.0188(3) Uani 1 2 d S T P
N2 N 0.89648(10) 0.2500 0.05929(18) 0.0160(3) Uani 1 2 d S T P
N3 N 0.85212(11) 0.2500 -0.1222(2) 0.0224(3) Uani 1 2 d S T P
N4 N 0.75538(11) 0.2500 -0.0893(2) 0.0244(3) Uani 1 2 d S T P
N5 N 0.73423(10) 0.2500 0.1089(2) 0.0212(3) Uani 1 2 d S T P
O1 O 1.06280(9) 0.2500 -0.04437(18) 0.0257(3) Uani 1 2 d S T P
C1 C 1.00262(12) 0.2500 0.0908(2) 0.0171(3) Uani 1 2 d S T P
C2 C 0.82319(11) 0.2500 0.1998(2) 0.0158(3) Uani 1 2 d S T P
C3 C 0.85267(12) 0.2500 0.4018(2) 0.0177(3) Uani 1 2 d S T P
C4 C 0.95352(12) 0.2500 0.4363(2) 0.0176(3) Uani 1 2 d S T P
H1 H 0.8009(14) 0.2500 0.505(3) 0.022(5) Uiso 1 2 d S . P
H2 H 0.9780(15) 0.2500 0.570(3) 0.024(5) Uiso 1 2 d S . P
H3 H 1.0902(17) 0.2500 0.322(3) 0.033(6) Uiso 1 2 d S . P
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
N1 0.0160(6) 0.0224(6) 0.0181(7) 0.000 -0.0004(5) 0.000
N2 0.0181(6) 0.0193(6) 0.0107(5) 0.000 0.0022(5) 0.000
N3 0.0259(7) 0.0281(7) 0.0133(6) 0.000 -0.0021(5) 0.000
N4 0.0248(7) 0.0293(7) 0.0191(6) 0.000 -0.0046(6) 0.000
N5 0.0172(6) 0.0271(7) 0.0193(6) 0.000 -0.0016(5) 0.000
O1 0.0236(6) 0.0299(6) 0.0235(6) 0.000 0.0117(5) 0.000
C1 0.0170(7) 0.0167(7) 0.0177(7) 0.000 0.0032(6) 0.000
C2 0.0169(7) 0.0167(6) 0.0139(6) 0.000 0.0023(5) 0.000
C3 0.0196(7) 0.0211(7) 0.0123(6) 0.000 0.0016(5) 0.000
C4 0.0216(7) 0.0177(7) 0.0134(6) 0.000 -0.0003(6) 0.000
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
C1 N1 C4 125.18(14)
C1 N1 H3 117.9(14)
C4 N1 H3 116.9(14)
C2 N2 N3 109.23(13)
C2 N2 C1 126.69(13)
N3 N2 C1 124.08(12)
N4 N3 N2 105.46(12)
N3 N4 N5 111.64(13)
C2 N5 N4 106.03(13)
O1 C1 N1 126.93(15)
O1 C1 N2 122.17(14)
N1 C1 N2 110.91(13)
N5 C2 N2 107.64(14)
N5 C2 C3 133.55(14)
N2 C2 C3 118.81(14)
C4 C3 C2 115.81(14)
C4 C3 H1 124.3(11)
C2 C3 H1 119.8(11)
C3 C4 N1 122.60(14)
C3 C4 H2 119.5(12)
N1 C4 H2 117.9(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.356(2)
N1 C4 1.378(2)
N1 H3 0.90(2)
N2 C2 1.3533(19)
N2 N3 1.3595(18)
N2 C1 1.411(2)
N3 N4 1.291(2)
N4 N5 1.3700(19)
N5 C2 1.321(2)
O1 C1 1.2090(18)
C2 C3 1.422(2)
C3 C4 1.346(2)
C3 H1 0.974(19)
C4 H2 0.96(2)
