#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:02:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180488 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/57/7215752.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_7215752
loop_
_publ_author_name
'Sankararaman, Sethuraman'
'V, Ramkumar'
'Sureshbabu, Beemineni'
_publ_section_title
;
 Substituent effect on the formation of helical to layered hydrogen bond
 network in hydroxyl and carboxyl substituted 1-aryl-1H-1,2,3-triazoles.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/c4ce00738g
_journal_year                    2014
_chemical_formula_moiety         'C9 H7 N3 O3'
_chemical_formula_sum            'C9 H7 N3 O3'
_chemical_formula_weight         205.18
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 107.607(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5117(7)
_cell_length_b                   5.1416(2)
_cell_length_c                   12.3092(6)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.59
_cell_measurement_theta_min      2.95
_cell_volume                     875.41(7)
_computing_cell_refinement       'APEXII/SAINT, Bruker,2004'
_computing_data_collection       'APEXII, Bruker,2004'
_computing_data_reduction        'SAINT PLUS/XPREP, Bruker,2004'
_computing_molecular_graphics    'ORTEP-3   (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5304
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' SADABS (Bruker,2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0323
_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)+(0.1000P)²+0.1258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1300
_reflns_number_total             1521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00738g1.cif
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7215752
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.12585(12) 0.8697(3) 0.28690(13) 0.0344(4) Uani 1 1 d .
H1 H 0.1193 0.9907 0.2289 0.041 Uiso 1 1 calc R
C2 C 0.06684(12) 0.8833(3) 0.35636(15) 0.0385(4) Uani 1 1 d .
H2 H 0.0203 1.0130 0.3456 0.046 Uiso 1 1 calc R
C3 C 0.07806(12) 0.7013(3) 0.44194(15) 0.0377(4) Uani 1 1 d .
H3 H 0.0386 0.7101 0.4889 0.045 Uiso 1 1 calc R
C4 C 0.14645(11) 0.5067(3) 0.45945(14) 0.0337(4) Uani 1 1 d .
H4 H 0.1523 0.3857 0.5173 0.040 Uiso 1 1 calc R
C5 C 0.20692(10) 0.4916(3) 0.39027(13) 0.0281(4) Uani 1 1 d .
C6 C 0.19451(10) 0.6760(3) 0.30404(12) 0.0278(4) Uani 1 1 d .
C7 C 0.35141(11) 0.7274(3) 0.13188(12) 0.0295(4) Uani 1 1 d .
C8 C 0.32207(11) 0.8270(3) 0.21885(13) 0.0301(4) Uani 1 1 d .
H8 H 0.3443 0.9767 0.2611 0.036 Uiso 1 1 calc R
C9 C 0.42076(11) 0.8338(3) 0.07802(14) 0.0333(4) Uani 1 1 d .
N1 N 0.25417(9) 0.6617(2) 0.22997(10) 0.0284(3) Uani 1 1 d .
N2 N 0.24084(10) 0.4653(2) 0.15304(11) 0.0351(4) Uani 1 1 d .
N3 N 0.30009(10) 0.5074(3) 0.09373(12) 0.0340(4) Uani 1 1 d .
O1 O 0.27786(8) 0.3130(2) 0.40321(10) 0.0367(3) Uani 1 1 d .
O2 O 0.46663(9) 1.0364(3) 0.12509(11) 0.0506(4) Uani 1 1 d D
O3 O 0.42943(9) 0.7273(2) -0.00979(10) 0.0442(4) Uani 1 1 d .
H1O H 0.2834(15) 0.216(4) 0.465(2) 0.061(6) Uiso 1 1 d .
H2O H 0.505(2) 1.109(8) 0.082(3) 0.177(17) Uiso 1 1 d 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 0.0410(9) 0.0303(8) 0.0312(8) 0.0020(6) 0.0098(7) -0.0001(7)
C2 0.0367(9) 0.0345(9) 0.0461(10) -0.0029(8) 0.0152(7) 0.0034(7)
C3 0.0378(9) 0.0398(10) 0.0419(10) -0.0075(7) 0.0216(8) -0.0055(7)
C4 0.0400(9) 0.0330(9) 0.0319(9) 0.0017(6) 0.0166(7) -0.0057(7)
C5 0.0303(8) 0.0262(8) 0.0277(8) -0.0029(6) 0.0086(6) -0.0041(6)
C6 0.0327(8) 0.0276(8) 0.0245(8) -0.0029(6) 0.0111(6) -0.0048(6)
C7 0.0310(8) 0.0304(8) 0.0276(8) 0.0009(6) 0.0096(6) 0.0016(6)
C8 0.0341(8) 0.0297(8) 0.0267(8) -0.0008(6) 0.0095(6) -0.0043(6)
C9 0.0311(8) 0.0376(9) 0.0322(8) 0.0016(7) 0.0113(7) 0.0022(7)
N1 0.0366(7) 0.0262(7) 0.0247(6) -0.0017(5) 0.0130(5) -0.0026(5)
N2 0.0485(8) 0.0299(7) 0.0315(7) -0.0049(6) 0.0189(6) -0.0065(6)
N3 0.0427(8) 0.0318(8) 0.0312(7) -0.0026(5) 0.0166(6) -0.0012(6)
O1 0.0433(7) 0.0343(7) 0.0374(7) 0.0085(5) 0.0193(5) 0.0058(5)
O2 0.0512(8) 0.0610(9) 0.0461(8) -0.0136(6) 0.0246(6) -0.0222(6)
O3 0.0477(7) 0.0494(8) 0.0442(8) -0.0076(6) 0.0269(6) -0.0022(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
C6 C1 C2 119.71(14)
C6 C1 H1 120.1
C2 C1 H1 120.1
C3 C2 C1 119.02(15)
C3 C2 H2 120.5
C1 C2 H2 120.5
C4 C3 C2 121.59(15)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 119.98(14)
C3 C4 H4 120.0
C5 C4 H4 120.0
O1 C5 C6 118.03(13)
O1 C5 C4 124.18(14)
C6 C5 C4 117.78(13)
C1 C6 C5 121.91(13)
C1 C6 N1 119.07(13)
C5 C6 N1 119.01(13)
N3 C7 C8 108.37(13)
N3 C7 C9 122.23(14)
C8 C7 C9 129.29(15)
N1 C8 C7 104.81(13)
N1 C8 H8 127.6
C7 C8 H8 127.6
O3 C9 O2 125.02(14)
O3 C9 C7 119.28(15)
O2 C9 C7 115.68(14)
C8 N1 N2 110.78(12)
C8 N1 C6 129.48(12)
N2 N1 C6 119.64(11)
N3 N2 N1 106.76(11)
N2 N3 C7 109.29(13)
C5 O1 H1O 110.5(14)
C9 O2 H2O 112(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.379(2)
C1 C2 1.383(2)
C1 H1 0.9300
C2 C3 1.381(2)
C2 H2 0.9300
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.398(2)
C4 H4 0.9300
C5 O1 1.3525(18)
C5 C6 1.393(2)
C6 N1 1.4364(18)
C7 N3 1.358(2)
C7 C8 1.366(2)
C7 C9 1.468(2)
C8 N1 1.3393(19)
C8 H8 0.9300
C9 O3 1.2515(19)
C9 O2 1.277(2)
N1 N2 1.3576(18)
N2 N3 1.3035(17)
O1 H1O 0.89(2)
O2 H2O 0.955(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N3 0.89(2) 1.92(2) 2.8038(17) 177(2) 4_566
O2 H2O O3 0.955(19) 1.71(2) 2.6574(16) 173(4) 3_675
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
C6 C1 C2 C3 0.0(2)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 0.5(2)
C3 C4 C5 O1 177.90(14)
C3 C4 C5 C6 -0.7(2)
C2 C1 C6 C5 -0.3(2)
C2 C1 C6 N1 178.95(13)
O1 C5 C6 C1 -178.09(13)
C4 C5 C6 C1 0.6(2)
O1 C5 C6 N1 2.7(2)
C4 C5 C6 N1 -178.61(13)
N3 C7 C8 N1 0.22(17)
C9 C7 C8 N1 176.38(15)
N3 C7 C9 O3 4.0(2)
C8 C7 C9 O3 -171.69(15)
N3 C7 C9 O2 -177.54(14)
C8 C7 C9 O2 6.8(2)
C7 C8 N1 N2 -0.09(17)
C7 C8 N1 C6 -176.34(14)
C1 C6 N1 C8 67.0(2)
C5 C6 N1 C8 -113.72(16)
C1 C6 N1 N2 -108.92(16)
C5 C6 N1 N2 70.31(19)
C8 N1 N2 N3 -0.08(17)
C6 N1 N2 N3 176.59(12)
N1 N2 N3 C7 0.22(17)
C8 C7 N3 N2 -0.28(18)
C9 C7 N3 N2 -176.77(14)
