#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:14:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180418 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/87/7208763.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_7208763
loop_
_publ_author_name
'Jordão, Alessandro K.'
'Ferreira, Vitor F.'
'Cunha, Anna C.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 The differing influence of halides upon supramolecular aggregation
 through C--X⋯π interactions in the crystal structures of
 (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X
 = H, F and Cl
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6534
_journal_paper_doi               10.1039/c2ce25841b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C10 H12 N4 O'
_chemical_formula_sum            'C10 H12 N4 O'
_chemical_formula_weight         204.24
_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                 96.751(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7842(19)
_cell_length_b                   7.258(2)
_cell_length_c                   21.155(6)
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.6670
_cell_measurement_theta_min      2.8062
_cell_volume                     1034.4(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & Brandenburg (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25445
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0525
_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)+(0.0739P)²+0.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                2320
_reflns_number_total             2363
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c2ce25841b.txt
_cod_data_source_block           h
_cod_original_cell_volume        1034.5(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7208763
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
O1 O 0.78303(15) 0.40823(14) 0.54326(5) 0.0302(3) Uani 1 1 d D
H1O H 0.707(3) 0.500(2) 0.5460(10) 0.045 Uiso 1 1 d D
N1 N 0.43738(19) 0.27380(17) 0.44557(6) 0.0311(3) Uani 1 1 d .
N2 N 0.33629(18) 0.13230(17) 0.41977(6) 0.0315(3) Uani 1 1 d .
N3 N 0.47378(17) 0.00611(16) 0.40802(5) 0.0264(3) Uani 1 1 d .
N4 N 0.41952(18) -0.16249(16) 0.37950(6) 0.0283(3) Uani 1 1 d D
H4N H 0.347(2) -0.229(2) 0.4037(7) 0.034 Uiso 1 1 d D
C1 C 0.7868(2) 0.3769(2) 0.47668(7) 0.0311(3) Uani 1 1 d .
H1A H 0.9208 0.3339 0.4694 0.037 Uiso 1 1 calc R
H1B H 0.7614 0.4948 0.4536 0.037 Uiso 1 1 calc R
C2 C 0.6363(2) 0.23763(19) 0.45014(6) 0.0271(3) Uani 1 1 d .
C3 C 0.6620(2) 0.06440(19) 0.42602(6) 0.0260(3) Uani 1 1 d .
C4 C 0.8391(2) -0.0499(2) 0.41737(8) 0.0355(4) Uani 1 1 d .
H4A H 0.8407 -0.1594 0.4445 0.053 Uiso 1 1 calc R
H4B H 0.9599 0.0223 0.4292 0.053 Uiso 1 1 calc R
H4C H 0.8333 -0.0877 0.3727 0.053 Uiso 1 1 calc R
C5 C 0.3297(2) -0.15004(18) 0.31516(6) 0.0267(3) Uani 1 1 d .
C6 C 0.4006(2) -0.0283(2) 0.27220(7) 0.0329(3) Uani 1 1 d .
H6 H 0.5075 0.0525 0.2856 0.039 Uiso 1 1 calc R
C7 C 0.3127(2) -0.0267(2) 0.20914(7) 0.0357(4) Uani 1 1 d .
H7 H 0.3597 0.0563 0.1796 0.043 Uiso 1 1 calc R
C8 C 0.1571(2) -0.1453(2) 0.18921(7) 0.0346(4) Uani 1 1 d .
H8 H 0.0972 -0.1425 0.1463 0.042 Uiso 1 1 calc R
C9 C 0.0894(2) -0.2681(2) 0.23221(7) 0.0359(4) Uani 1 1 d .
H9 H -0.0158 -0.3506 0.2186 0.043 Uiso 1 1 calc R
C10 C 0.1754(2) -0.2704(2) 0.29521(7) 0.0322(3) Uani 1 1 d .
H10 H 0.1287 -0.3541 0.3246 0.039 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'
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 O1 H1O 105.9(14)
N2 N1 C2 109.95(12)
N1 N2 N3 105.53(11)
N2 N3 C3 112.60(12)
N2 N3 N4 121.45(11)
C3 N3 N4 125.94(12)
N3 N4 C5 114.74(11)
N3 N4 H4N 111.1(12)
C5 N4 H4N 112.2(12)
O1 C1 C2 112.70(11)
O1 C1 H1A 109.1
C2 C1 H1A 109.1
O1 C1 H1B 109.1
C2 C1 H1B 109.1
H1A C1 H1B 107.8
N1 C2 C3 108.45(12)
N1 C2 C1 121.37(13)
C3 C2 C1 130.16(13)
N3 C3 C2 103.47(12)
N3 C3 C4 122.57(13)
C2 C3 C4 133.96(13)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 C5 C6 120.38(13)
C10 C5 N4 118.14(12)
C6 C5 N4 121.38(12)
C5 C6 C7 119.16(14)
C5 C6 H6 120.4
C7 C6 H6 120.4
C8 C7 C6 120.62(14)
C8 C7 H7 119.7
C6 C7 H7 119.7
C9 C8 C7 119.78(14)
C9 C8 H8 120.1
C7 C8 H8 120.1
C10 C9 C8 120.07(14)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C5 119.97(14)
C9 C10 H10 120.0
C5 C10 H10 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4301(17)
O1 H1O 0.850(9)
N1 N2 1.3172(17)
N1 C2 1.3668(19)
N2 N3 1.3510(17)
N3 C3 1.3565(17)
N3 N4 1.3946(16)
N4 C5 1.4273(18)
N4 H4N 0.893(9)
C1 C2 1.4986(19)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.376(2)
C3 C4 1.489(2)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C10 1.3903(19)
C5 C6 1.393(2)
C6 C7 1.396(2)
C6 H6 0.9500
C7 C8 1.388(2)
C7 H7 0.9500
C8 C9 1.390(2)
C8 H8 0.9500
C9 C10 1.391(2)
C9 H9 0.9500
C10 H10 0.9500
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
C2 N1 N2 N3 -0.04(15)
N1 N2 N3 C3 0.11(16)
N1 N2 N3 N4 -179.01(11)
N2 N3 N4 C5 66.22(16)
C3 N3 N4 C5 -112.78(15)
N2 N1 C2 C3 -0.04(16)
N2 N1 C2 C1 178.79(12)
O1 C1 C2 N1 68.12(17)
O1 C1 C2 C3 -113.35(16)
N2 N3 C3 C2 -0.13(15)
N4 N3 C3 C2 178.94(12)
N2 N3 C3 C4 -179.43(13)
N4 N3 C3 C4 -0.4(2)
N1 C2 C3 N3 0.10(15)
C1 C2 C3 N3 -178.59(14)
N1 C2 C3 C4 179.28(15)
C1 C2 C3 C4 0.6(3)
N3 N4 C5 C10 -142.60(13)
N3 N4 C5 C6 40.93(18)
C10 C5 C6 C7 1.0(2)
N4 C5 C6 C7 177.42(13)
C5 C6 C7 C8 -0.3(2)
C6 C7 C8 C9 -0.6(2)
C7 C8 C9 C10 0.9(2)
C8 C9 C10 C5 -0.2(2)
C6 C5 C10 C9 -0.8(2)
N4 C5 C10 C9 -177.29(13)
