#------------------------------------------------------------------------------
#$Date: 2022-04-04 11:47:24 +0200 (lun 04 de abr de 2022) $
#$Revision: 274325 $
#$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500121.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_3500121
loop_
_publ_author_name
'José Manuel Méndez-Arriaga'
'Miguel Quirós'
_journal_name_full               'Personal communication to COD'
_journal_year                    2022
_chemical_formula_moiety         'C6 H5 Cl N4'
_chemical_formula_sum            'C6 H5 Cl N4'
_chemical_formula_weight         168.59
_chemical_name_systematic
7-chloro-5-methyl-1,2,4-triazolo-[1,5-a]pyrimidine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                90
_cell_angle_beta                 91.318(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3768(5)
_cell_length_b                   12.0691(8)
_cell_length_c                   6.8173(4)
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.212
_cell_measurement_theta_min      3.663
_cell_volume                     689.05(7)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.898
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3921
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.256
_diffrn_reflns_theta_min         5.282
_exptl_absorpt_coefficient_mu    4.339
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             344
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0363
_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)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1111
_reflns_number_total             1159
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            clmtp.cif
_cod_data_source_block           clmtp
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               3500121
_shelx_shelxl_version_number     2019/2
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40796(16) 0.29270(12) 0.4179(2) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.3953(2) 0.18343(15) 0.4071(2) 0.0199(4) Uani 1 1 d . . . . .
H2 H 0.482054 0.136644 0.444219 0.024 Uiso 1 1 d R U . . .
N3 N 0.25452(16) 0.14073(12) 0.3412(2) 0.0193(3) Uani 1 1 d . . . . .
C3A C 0.16816(19) 0.23145(14) 0.3052(2) 0.0161(4) Uani 1 1 d . . . . .
N4 N 0.01734(16) 0.23841(12) 0.2343(2) 0.0174(3) Uani 1 1 d . . . . .
C5 C -0.04282(19) 0.33930(14) 0.2143(2) 0.0178(4) Uani 1 1 d . . . . .
C51 C -0.20969(19) 0.34911(15) 0.1308(3) 0.0216(4) Uani 1 1 d . . . . .
H51 H -0.280012 0.298044 0.199750 0.032 Uiso 1 1 d R U . . .
H52 H -0.210146 0.330461 -0.009098 0.032 Uiso 1 1 d R U . . .
H53 H -0.247819 0.425233 0.147362 0.032 Uiso 1 1 d R U . . .
C6 C 0.04435(19) 0.43707(14) 0.2634(2) 0.0186(4) Uani 1 1 d . . . . .
H6 H -0.003854 0.507911 0.248483 0.022 Uiso 1 1 d R U . . .
C7 C 0.19763(19) 0.42774(14) 0.3319(2) 0.0179(4) Uani 1 1 d . . . . .
Cl7 Cl 0.31969(5) 0.53575(3) 0.39415(6) 0.0230(2) Uani 1 1 d . . . . .
N8 N 0.25961(15) 0.32407(12) 0.35124(19) 0.0156(3) 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
N1 0.0150(7) 0.0245(9) 0.0173(7) 0.0004(5) -0.0011(5) 0.0024(6)
C2 0.0194(8) 0.0224(10) 0.0179(8) 0.0001(7) 0.0011(6) 0.0033(7)
N3 0.0201(7) 0.0185(8) 0.0192(8) 0.0004(5) 0.0009(6) 0.0010(5)
C3A 0.0183(8) 0.0174(9) 0.0128(8) -0.0009(6) 0.0031(6) -0.0019(6)
N4 0.0168(7) 0.0203(8) 0.0152(7) -0.0008(5) 0.0010(5) -0.0018(5)
C5 0.0187(8) 0.0220(10) 0.0128(8) 0.0004(6) 0.0027(6) 0.0016(7)
C51 0.0180(8) 0.0241(10) 0.0225(9) -0.0026(6) -0.0034(7) 0.0001(7)
C6 0.0204(9) 0.0171(9) 0.0184(9) -0.0001(6) 0.0018(7) 0.0009(7)
C7 0.0201(8) 0.0183(9) 0.0152(8) 0.0004(6) 0.0019(6) -0.0009(7)
Cl7 0.0222(3) 0.0186(3) 0.0280(3) -0.00058(14) -0.0039(2) -0.00495(14)
N8 0.0140(7) 0.0185(8) 0.0142(7) 0.0000(5) 0.0002(5) -0.0004(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 N8 100.73(13) . .
N1 C2 N3 117.73(15) . .
N1 C2 H2 121.1 . .
N3 C2 H2 121.1 . .
C3A N3 C2 102.33(14) . .
N3 C3A N4 128.27(15) . .
N3 C3A N8 109.02(14) . .
N4 C3A N8 122.71(14) . .
C5 N4 C3A 116.55(14) . .
N4 C5 C6 123.11(15) . .
N4 C5 C51 117.42(14) . .
C6 C5 C51 119.45(14) . .
C5 C51 H51 109.5 . .
C5 C51 H52 109.5 . .
H51 C51 H52 109.5 . .
C5 C51 H53 109.5 . .
H51 C51 H53 109.5 . .
H52 C51 H53 109.5 . .
C7 C6 C5 119.14(15) . .
C7 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
N8 C7 C6 117.68(15) . .
N8 C7 Cl7 117.01(12) . .
C6 C7 Cl7 125.32(14) . .
C7 N8 N1 128.99(14) . .
C7 N8 C3A 120.79(14) . .
N1 N8 C3A 110.20(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.325(2) .
N1 N8 1.367(2) .
C2 N3 1.354(2) .
C2 H2 0.9500 .
N3 C3A 1.332(2) .
C3A N4 1.345(2) .
C3A N8 1.387(2) .
N4 C5 1.324(2) .
C5 C6 1.423(2) .
C5 C51 1.502(2) .
C51 H51 0.9800 .
C51 H52 0.9800 .
C51 H53 0.9800 .
C6 C7 1.361(2) .
C6 H6 0.9500 .
C7 N8 1.360(2) .
C7 Cl7 1.7044(17) .

_cod_database_fobs_code 3500121
