#------------------------------------------------------------------------------
#$Date: 2019-11-23 10:10:12 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 233023 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/30/1553075.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_1553075
loop_
_publ_author_name
'Quinodoz, Pierre'
'Lo, Cheikh'
'Kletskii, Mikhail'
'Burov, Oleg'
'Marrot, Jérôme'
'Couty, François'
_publ_section_title
;
 Regio- and stereoselective synthesis of α-hydroxy-β-azido tetrazoles
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              492
_journal_paper_doi               10.1039/C4QO00345D
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C9 H9 N7 O'
_chemical_formula_weight         231.23
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-28 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9162(8)
_cell_length_b                   14.8123(11)
_cell_length_c                   7.3118(6)
_cell_measurement_reflns_used    9531
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.75
_cell_volume                     1073.97(15)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            33251
_diffrn_reflns_theta_full        30.13
_diffrn_reflns_theta_max         30.13
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.1163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                1462
_reflns_number_total             1687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00345d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               1553075
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
O1 O 0.77909(10) 0.33818(9) 0.97153(19) 0.0239(3) Uani 1 1 d .
H1A H 0.8271 0.3252 0.8806 0.036 Uiso 1 1 calc R
C1 C 0.65461(19) 0.15180(13) 0.9496(3) 0.0317(4) Uani 1 1 d .
H1 H 0.7152 0.1693 1.0438 0.038 Uiso 1 1 calc R
C2 C 0.6663(2) 0.06717(14) 0.8695(4) 0.0413(6) Uani 1 1 d .
H2 H 0.7358 0.0273 0.9082 0.050 Uiso 1 1 calc R
C3 C 0.5779(3) 0.04042(14) 0.7341(4) 0.0464(6) Uani 1 1 d .
H3 H 0.5856 -0.0180 0.6813 0.056 Uiso 1 1 calc R
C4 C 0.4786(3) 0.09867(15) 0.6759(4) 0.0479(6) Uani 1 1 d .
H4 H 0.4180 0.0805 0.5822 0.057 Uiso 1 1 calc R
C5 C 0.4666(2) 0.18395(13) 0.7538(3) 0.0338(4) Uani 1 1 d .
H5 H 0.3982 0.2239 0.7121 0.041 Uiso 1 1 calc R
C6 C 0.55379(17) 0.21136(12) 0.8919(3) 0.0235(4) Uani 1 1 d .
C7 C 0.53840(16) 0.30450(11) 0.9729(2) 0.0202(3) Uani 1 1 d .
H7 H 0.4503 0.3301 0.9312 0.024 Uiso 1 1 calc R
C8 C 0.65116(15) 0.36817(11) 0.9114(2) 0.0187(3) Uani 1 1 d .
H8 H 0.6516 0.3704 0.7747 0.022 Uiso 1 1 calc R
C9 C 0.63538(14) 0.46257(11) 0.9829(2) 0.0184(3) Uani 1 1 d .
N1 N 0.52530(13) 0.51005(10) 1.0133(2) 0.0242(3) Uani 1 1 d .
N2 N 0.56736(14) 0.59316(10) 1.0724(3) 0.0284(4) Uani 1 1 d .
N3 N 0.69765(14) 0.59628(10) 1.0788(3) 0.0276(3) Uani 1 1 d .
N4 N 0.74110(14) 0.51482(9) 1.0227(2) 0.0214(3) Uani 1 1 d .
H4A H 0.824(2) 0.5036(16) 1.020(4) 0.042(7) Uiso 1 1 d .
N5 N 0.53920(15) 0.30304(12) 1.1780(2) 0.0264(3) Uani 1 1 d .
N6 N 0.44715(16) 0.25587(11) 1.2417(3) 0.0284(3) Uani 1 1 d .
N7 N 0.3683(2) 0.21459(16) 1.3123(3) 0.0519(6) 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
O1 0.0136(5) 0.0320(6) 0.0262(7) -0.0028(5) 0.0017(5) 0.0045(4)
C1 0.0354(9) 0.0272(9) 0.0324(12) 0.0049(8) -0.0031(9) 0.0002(7)
C2 0.0507(13) 0.0252(10) 0.0479(14) 0.0091(10) 0.0080(11) 0.0041(9)
C3 0.0727(16) 0.0249(10) 0.0416(13) -0.0023(10) 0.0103(13) -0.0058(10)
C4 0.0683(16) 0.0359(12) 0.0395(13) -0.0078(11) -0.0112(13) -0.0145(11)
C5 0.0372(10) 0.0314(10) 0.0327(10) -0.0008(9) -0.0089(9) -0.0053(8)
C6 0.0247(8) 0.0238(8) 0.0219(9) 0.0018(7) 0.0016(7) -0.0041(6)
C7 0.0171(7) 0.0259(8) 0.0175(8) -0.0009(7) -0.0018(6) -0.0015(6)
C8 0.0143(6) 0.0240(8) 0.0179(8) -0.0003(7) 0.0002(6) 0.0015(6)
C9 0.0141(6) 0.0249(8) 0.0163(8) 0.0007(6) 0.0000(6) -0.0011(5)
N1 0.0153(6) 0.0266(7) 0.0309(9) -0.0023(7) 0.0012(6) 0.0005(5)
N2 0.0187(6) 0.0283(7) 0.0382(9) -0.0049(7) 0.0017(7) 0.0015(5)
N3 0.0195(6) 0.0262(7) 0.0370(9) -0.0049(7) 0.0001(7) 0.0002(5)
N4 0.0129(6) 0.0241(6) 0.0272(8) -0.0011(6) 0.0006(6) 0.0007(5)
N5 0.0225(7) 0.0382(9) 0.0186(7) -0.0009(7) 0.0019(6) -0.0101(6)
N6 0.0247(7) 0.0381(8) 0.0223(8) 0.0010(7) -0.0007(6) -0.0069(6)
N7 0.0445(11) 0.0704(14) 0.0407(12) 0.0121(11) 0.0018(9) -0.0263(10)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C8 O1 H1A 109.5
C2 C1 C6 120.14(19)
C2 C1 H1 119.9
C6 C1 H1 119.9
C3 C2 C1 120.6(2)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 119.7(2)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.2(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 120.6(2)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 118.65(18)
C5 C6 C7 119.30(16)
C1 C6 C7 122.05(16)
N5 C7 C6 112.25(15)
N5 C7 C8 107.41(14)
C6 C7 C8 111.96(14)
N5 C7 H7 108.4
C6 C7 H7 108.4
C8 C7 H7 108.4
O1 C8 C9 106.12(13)
O1 C8 C7 111.73(13)
C9 C8 C7 113.28(13)
O1 C8 H8 108.5
C9 C8 H8 108.5
C7 C8 H8 108.5
N1 C9 N4 107.73(14)
N1 C9 C8 129.97(14)
N4 C9 C8 122.28(13)
C9 N1 N2 106.30(13)
N3 N2 N1 110.34(14)
N2 N3 N4 106.06(14)
C9 N4 N3 109.57(14)
C9 N4 H4A 130.6(17)
N3 N4 H4A 119.8(18)
N6 N5 C7 112.32(16)
N7 N6 N5 174.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.4143(18)
O1 H1A 0.8400
C1 C2 1.389(3)
C1 C6 1.398(3)
C1 H1 0.9500
C2 C3 1.380(4)
C2 H2 0.9500
C3 C4 1.377(4)
C3 H3 0.9500
C4 C5 1.391(3)
C4 H4 0.9500
C5 C6 1.390(3)
C5 H5 0.9500
C6 C7 1.509(3)
C7 N5 1.499(2)
C7 C8 1.530(2)
C7 H7 1.0000
C8 C9 1.501(2)
C8 H8 1.0000
C9 N1 1.317(2)
C9 N4 1.335(2)
N1 N2 1.370(2)
N2 N3 1.294(2)
N3 N4 1.345(2)
N4 H4A 0.84(2)
N5 N6 1.240(2)
N6 N7 1.119(2)
