#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/95/2229579.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229579
loop_
_publ_author_name
'Dong, Su-Lan'
'Cheng, Xiao-Chun'
_publ_section_title
;
 Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate
;
_journal_coeditor_code           BQ2275
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o769
_journal_paper_doi               10.1107/S1600536811006684
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H9 F2 N3 O2'
_chemical_formula_moiety         'C11 H9 F2 N3 O2'
_chemical_formula_sum            'C11 H9 F2 N3 O2'
_chemical_formula_weight         253.21
_chemical_name_systematic
;
Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4570(17)
_cell_length_b                   5.4140(11)
_cell_length_c                   12.125(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     554.72(18)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2187
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       spiculate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1146
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0320
_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)+(0.0542P)²+0.0317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                1035
_reflns_number_total             1146
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2275.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2229579
_cod_database_fobs_code          2229579
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4481(2) 0.4288(4) 0.80667(14) 0.0340(5) Uani d . 1 . .
F F1 0.67849(18) 0.9724(4) 0.74993(14) 0.0589(5) Uani d . 1 . .
O O1 0.3504(3) 0.2067(5) 0.47974(15) 0.0642(6) Uani d . 1 . .
C C1 0.7743(3) 0.7947(5) 0.7942(2) 0.0409(6) Uani d . 1 . .
F F2 0.74809(18) 0.2564(4) 0.96110(13) 0.0595(5) Uani d . 1 . .
N N2 0.3697(2) 0.2386(5) 0.85061(16) 0.0424(5) Uani d . 1 . .
O O2 0.2160(2) -0.0844(5) 0.56720(16) 0.0613(6) Uani d . 1 . .
C C2 0.9334(3) 0.8063(6) 0.7754(2) 0.0500(7) Uani d . 1 . .
H H2B 0.9745 0.9332 0.7336 0.060 Uiso calc R 1 . .
N N3 0.3078(2) 0.1088(5) 0.76968(17) 0.0436(5) Uani d . 1 . .
C C3 1.0299(3) 0.6249(7) 0.8204(2) 0.0527(7) Uani d . 1 . .
H H3B 1.1377 0.6284 0.8080 0.063 Uiso calc R 1 . .
C C4 0.9699(3) 0.4388(7) 0.8831(2) 0.0517(7) Uani d . 1 . .
H H4A 1.0354 0.3168 0.9137 0.062 Uiso calc R 1 . .
C C5 0.8097(3) 0.4382(5) 0.89946(19) 0.0409(6) Uani d . 1 . .
C C6 0.7066(3) 0.6141(5) 0.85681(19) 0.0361(5) Uani d . 1 . .
C C7 0.5322(3) 0.6069(5) 0.87801(19) 0.0373(6) Uani d . 1 . .
H H7A 0.5179 0.5633 0.9546 0.045 Uiso calc R 1 . .
H H7B 0.4873 0.7699 0.8655 0.045 Uiso calc R 1 . .
C C8 0.4362(3) 0.4207(6) 0.69632(18) 0.0374(5) Uani d . 1 . .
H H8A 0.4792 0.5303 0.6466 0.045 Uiso calc R 1 . .
C C9 0.3472(3) 0.2167(5) 0.67313(19) 0.0368(6) Uani d . 1 . .
C C10 0.3059(3) 0.1160(6) 0.5631(2) 0.0438(6) Uani d . 1 . .
C C11 0.1788(5) -0.2037(8) 0.4633(3) 0.0797(11) Uani d . 1 . .
H H11A 0.1137 -0.3457 0.4753 0.120 Uiso calc R 1 . .
H H11B 0.2749 -0.2545 0.4304 0.120 Uiso calc R 1 . .
H H11C 0.1229 -0.0904 0.4149 0.120 Uiso calc R 1 . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 N2 . . 110.6(2) ?
C8 N1 C7 . . 129.0(2) ?
N2 N1 C7 . . 120.43(18) ?
F1 C1 C2 . . 118.4(3) ?
F1 C1 C6 . . 117.9(2) ?
C2 C1 C6 . . 123.7(3) ?
N3 N2 N1 . . 107.75(18) ?
C10 O2 C11 . . 116.1(3) ?
C1 C2 C3 . . 118.1(3) ?
C1 C2 H2B . . 120.9 ?
C3 C2 H2B . . 120.9 ?
N2 N3 C9 . . 108.2(2) ?
C4 C3 C2 . . 121.1(2) ?
C4 C3 H3B . . 119.4 ?
C2 C3 H3B . . 119.4 ?
C3 C4 C5 . . 118.0(3) ?
C3 C4 H4A . . 121.0 ?
C5 C4 H4A . . 121.0 ?
F2 C5 C6 . . 117.3(2) ?
F2 C5 C4 . . 118.9(2) ?
C6 C5 C4 . . 123.8(3) ?
C5 C6 C1 . . 115.3(2) ?
C5 C6 C7 . . 121.8(2) ?
C1 C6 C7 . . 122.9(2) ?
N1 C7 C6 . . 111.9(2) ?
N1 C7 H7A . . 109.2 ?
C6 C7 H7A . . 109.2 ?
N1 C7 H7B . . 109.2 ?
C6 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
N1 C8 C9 . . 104.6(2) ?
N1 C8 H8A . . 127.7 ?
C9 C8 H8A . . 127.7 ?
C8 C9 N3 . . 108.9(2) ?
C8 C9 C10 . . 126.8(2) ?
N3 C9 C10 . . 124.3(2) ?
O1 C10 O2 . . 124.5(3) ?
O1 C10 C9 . . 122.8(3) ?
O2 C10 C9 . . 112.7(2) ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.339(3) ?
N1 N2 . 1.346(3) ?
N1 C7 . 1.461(3) ?
F1 C1 . 1.355(3) ?
O1 C10 . 1.198(3) ?
C1 C2 . 1.375(4) ?
C1 C6 . 1.376(4) ?
F2 C5 . 1.353(3) ?
N2 N3 . 1.300(3) ?
O2 C10 . 1.327(4) ?
O2 C11 . 1.439(4) ?
C2 C3 . 1.376(5) ?
C2 H2B . 0.9300 ?
N3 C9 . 1.362(3) ?
C3 C4 . 1.372(4) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.378(4) ?
C6 C7 . 1.507(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.360(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.471(4) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7B N3 1_565 0.97 2.62 3.538(4) 157
C8 H8A O1 2_656 0.93 2.35 3.243(3) 162
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 N2 N3 . . . . 0.0(3) ?
C7 N1 N2 N3 . . . . -179.3(2) ?
F1 C1 C2 C3 . . . . -179.8(2) ?
C6 C1 C2 C3 . . . . 1.1(4) ?
N1 N2 N3 C9 . . . . 0.1(3) ?
C1 C2 C3 C4 . . . . -0.7(5) ?
C2 C3 C4 C5 . . . . 0.3(4) ?
C3 C4 C5 F2 . . . . 180.0(2) ?
C3 C4 C5 C6 . . . . -0.3(4) ?
F2 C5 C6 C1 . . . . -179.7(2) ?
C4 C5 C6 C1 . . . . 0.6(4) ?
F2 C5 C6 C7 . . . . 0.4(4) ?
C4 C5 C6 C7 . . . . -179.3(3) ?
F1 C1 C6 C5 . . . . 179.9(2) ?
C2 C1 C6 C5 . . . . -1.0(4) ?
F1 C1 C6 C7 . . . . -0.2(4) ?
C2 C1 C6 C7 . . . . 178.9(3) ?
C8 N1 C7 C6 . . . . -59.3(3) ?
N2 N1 C7 C6 . . . . 119.9(2) ?
C5 C6 C7 N1 . . . . -79.4(3) ?
C1 C6 C7 N1 . . . . 100.6(3) ?
N2 N1 C8 C9 . . . . -0.2(3) ?
C7 N1 C8 C9 . . . . 179.1(2) ?
N1 C8 C9 N3 . . . . 0.2(3) ?
N1 C8 C9 C10 . . . . -176.5(2) ?
N2 N3 C9 C8 . . . . -0.2(3) ?
N2 N3 C9 C10 . . . . 176.6(2) ?
C11 O2 C10 O1 . . . . 3.4(4) ?
C11 O2 C10 C9 . . . . -176.1(3) ?
C8 C9 C10 O1 . . . . 1.0(4) ?
N3 C9 C10 O1 . . . . -175.3(3) ?
C8 C9 C10 O2 . . . . -179.4(2) ?
N3 C9 C10 O2 . . . . 4.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11587358
