#------------------------------------------------------------------------------
#$Date: 2023-06-30 00:53:48 +0300 (Fri, 30 Jun 2023) $
#$Revision: 284709 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/17/7131791.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_7131791
loop_
_publ_author_name
'Motornov, Vladimir'
'Pohl, Radek'
'Klepetarova, Blanka'
'Beier, Petr'
_publ_section_title
;
 N-Acyl-1,2,3-triazoles -- key intermediates in denitrogenative
 transformations
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC00987D
_journal_year                    2023
_chemical_formula_moiety         'C17 H15 N3 O2'
_chemical_formula_sum            'C17 H15 N3 O2'
_chemical_formula_weight         293.33
_chemical_name_systematic
(4-methoxyphenyl)(4-(p-tolyl)-1H-1,2,3-triazol-1-yl)methanone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2023-02-27 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                93.215(2)
_cell_angle_beta                 106.075(2)
_cell_angle_gamma                113.5933(19)
_cell_formula_units_Z            2
_cell_length_a                   8.1806(6)
_cell_length_b                   9.0341(6)
_cell_length_c                   11.2117(8)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    180
_cell_measurement_theta_max      68.4213
_cell_measurement_theta_min      4.1794
_cell_volume                     716.41(9)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20666
_diffrn_reflns_theta_full        68.415
_diffrn_reflns_theta_max         68.415
_diffrn_reflns_theta_min         4.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0128
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.0002223
_refine_ls_shift/su_mean         0.0000250
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.553 0.754 0.454 0.200 0.521E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0478
_refine_ls_wR_factor_gt          0.0471
_refine_ls_wR_factor_ref         0.0471
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2489
_reflns_number_total             2602
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.51
_oxford_diffrn_Wilson_scale      5.95
_oxford_refine_ls_r_factor_ref   0.0436
_oxford_refine_ls_scale          0.4765(11)
_oxford_reflns_number_all        2602
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            d3cc00987d2.cif
_cod_data_source_block           1_CCDC1
_cod_original_cell_volume        716.42(9)
_cod_database_code               7131791
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O -0.05626(13) 0.07193(11) -0.27252(8) 0.0462 1.0000 Uani . . . . . .
C2 C -0.14009(17) 0.04172(15) -0.19705(11) 0.0346 1.0000 Uani . . . . . .
N3 N -0.05839(14) 0.15959(12) -0.08145(9) 0.0335 1.0000 Uani . . . . . .
N4 N -0.10846(15) 0.13102(13) 0.02453(9) 0.0400 1.0000 Uani . . . . . .
N5 N 0.00156(15) 0.26167(14) 0.11089(10) 0.0412 1.0000 Uani . . . . . .
C6 C 0.12483(16) 0.37631(15) 0.06343(11) 0.0345 1.0000 Uani . . . . . .
C7 C 0.08730(17) 0.31099(15) -0.05871(11) 0.0356 1.0000 Uani . . . . . .
C8 C 0.26890(17) 0.53478(15) 0.14264(11) 0.0351 1.0000 Uani . . . . . .
C9 C 0.42525(18) 0.63012(16) 0.10902(12) 0.0405 1.0000 Uani . . . . . .
C10 C 0.5653(2) 0.77607(17) 0.18723(13) 0.0455 1.0000 Uani . . . . . .
C11 C 0.55385(19) 0.83088(16) 0.30157(12) 0.0443 1.0000 Uani . . . . . .
C12 C 0.3955(2) 0.73763(18) 0.33294(12) 0.0462 1.0000 Uani . . . . . .
C13 C 0.2548(2) 0.59199(17) 0.25578(12) 0.0418 1.0000 Uani . . . . . .
C14 C 0.7085(3) 0.9863(2) 0.38850(17) 0.0579 1.0000 Uani . . . . . .
C15 C -0.31894(16) -0.10593(14) -0.21920(11) 0.0323 1.0000 Uani . . . . . .
C16 C -0.36278(18) -0.23224(16) -0.31603(12) 0.0386 1.0000 Uani . . . . . .
C17 C -0.53221(18) -0.37192(15) -0.35264(12) 0.0380 1.0000 Uani . . . . . .
C18 C -0.66264(17) -0.38553(14) -0.29211(11) 0.0353 1.0000 Uani . . . . . .
O19 O -0.83533(13) -0.51581(11) -0.32181(9) 0.0463 1.0000 Uani . . . . . .
C20 C -0.8915(2) -0.63999(17) -0.42845(14) 0.0476 1.0000 Uani . . . . . .
C21 C -0.62078(19) -0.26104(16) -0.19459(13) 0.0417 1.0000 Uani . . . . . .
C22 C -0.45132(18) -0.12296(15) -0.15774(12) 0.0381 1.0000 Uani . . . . . .
H71 H 0.136(2) 0.3508(18) -0.1198(14) 0.0435 1.0000 Uiso . . . . . .
H91 H 0.438(2) 0.5935(19) 0.0306(15) 0.0501 1.0000 Uiso . . . . . .
H101 H 0.674(2) 0.839(2) 0.1632(15) 0.0553 1.0000 Uiso . . . . . .
H121 H 0.382(2) 0.775(2) 0.4098(16) 0.0574 1.0000 Uiso . . . . . .
H131 H 0.146(2) 0.5281(19) 0.2782(15) 0.0496 1.0000 Uiso . . . . . .
H142 H 0.662(3) 1.067(3) 0.402(2) 0.0881 1.0000 Uiso . . . . . .
H141 H 0.809(3) 1.037(3) 0.351(2) 0.0888 1.0000 Uiso . . . . . .
H143 H 0.755(3) 0.965(3) 0.468(2) 0.0879 1.0000 Uiso . . . . . .
H161 H -0.273(2) -0.2224(18) -0.3574(14) 0.0477 1.0000 Uiso . . . . . .
H171 H -0.557(2) -0.4593(19) -0.4165(15) 0.0469 1.0000 Uiso . . . . . .
H201 H -1.016(3) -0.717(2) -0.4297(18) 0.0718 1.0000 Uiso . . . . . .
H203 H -0.897(3) -0.597(2) -0.5060(18) 0.0693 1.0000 Uiso . . . . . .
H202 H -0.805(3) -0.696(2) -0.4146(17) 0.0704 1.0000 Uiso . . . . . .
H211 H -0.709(2) -0.2673(19) -0.1571(15) 0.0504 1.0000 Uiso . . . . . .
H221 H -0.426(2) -0.0337(19) -0.0902(15) 0.0461 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 116.47(11) yes
O1 . C2 . C15 . 123.59(11) yes
N3 . C2 . C15 . 119.94(10) yes
C2 . N3 . N4 . 124.52(10) yes
C2 . N3 . C7 . 125.12(10) yes
N4 . N3 . C7 . 110.24(10) yes
N3 . N4 . N5 . 106.84(10) yes
N4 . N5 . C6 . 109.87(10) yes
N5 . C6 . C7 . 107.80(11) yes
N5 . C6 . C8 . 121.27(11) yes
C7 . C6 . C8 . 130.90(12) yes
C6 . C7 . N3 . 105.25(11) yes
C6 . C7 . H71 . 133.0(9) no
N3 . C7 . H71 . 121.7(9) no
C6 . C8 . C9 . 121.30(11) yes
C6 . C8 . C13 . 120.53(12) yes
C9 . C8 . C13 . 118.15(12) yes
C8 . C9 . C10 . 120.97(12) yes
C8 . C9 . H91 . 119.9(9) no
C10 . C9 . H91 . 119.1(9) no
C9 . C10 . C11 . 120.89(14) yes
C9 . C10 . H101 . 119.6(10) no
C11 . C10 . H101 . 119.4(10) no
C10 . C11 . C12 . 117.84(12) yes
C10 . C11 . C14 . 121.01(15) yes
C12 . C11 . C14 . 121.15(14) yes
C11 . C12 . C13 . 121.82(13) yes
C11 . C12 . H121 . 119.4(10) no
C13 . C12 . H121 . 118.8(10) no
C8 . C13 . C12 . 120.28(14) yes
C8 . C13 . H131 . 118.3(9) no
C12 . C13 . H131 . 121.4(9) no
C11 . C14 . H142 . 111.4(13) no
C11 . C14 . H141 . 110.4(13) no
H142 . C14 . H141 . 106.6(18) no
C11 . C14 . H143 . 110.6(13) no
H142 . C14 . H143 . 105.7(18) no
H141 . C14 . H143 . 111.9(18) no
C2 . C15 . C16 . 115.89(11) yes
C2 . C15 . C22 . 125.60(11) yes
C16 . C15 . C22 . 118.34(11) yes
C15 . C16 . C17 . 121.71(11) yes
C15 . C16 . H161 . 118.9(9) no
C17 . C16 . H161 . 119.4(9) no
C16 . C17 . C18 . 119.16(11) yes
C16 . C17 . H171 . 120.3(9) no
C18 . C17 . H171 . 120.5(9) no
C17 . C18 . O19 . 124.29(11) yes
C17 . C18 . C21 . 119.93(11) yes
O19 . C18 . C21 . 115.77(11) yes
C18 . O19 . C20 . 117.83(11) yes
O19 . C20 . H201 . 102.1(11) no
O19 . C20 . H203 . 112.1(11) no
H201 . C20 . H203 . 111.6(15) no
O19 . C20 . H202 . 110.9(10) no
H201 . C20 . H202 . 109.8(15) no
H203 . C20 . H202 . 110.2(15) no
C18 . C21 . C22 . 120.69(12) yes
C18 . C21 . H211 . 120.1(10) no
C22 . C21 . H211 . 119.1(10) no
C15 . C22 . C21 . 120.16(12) yes
C15 . C22 . H221 . 120.3(9) no
C21 . C22 . H221 . 119.5(9) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2075(15) yes
C2 . N3 . 1.4340(15) yes
C2 . C15 . 1.4768(17) yes
N3 . N4 . 1.3658(14) yes
N3 . C7 . 1.3579(16) yes
N4 . N5 . 1.2960(15) yes
N5 . C6 . 1.3769(17) yes
C6 . C7 . 1.3598(17) yes
C6 . C8 . 1.4678(17) yes
C7 . H71 . 0.906(16) no
C8 . C9 . 1.3934(19) yes
C8 . C13 . 1.3945(18) yes
C9 . C10 . 1.3873(19) yes
C9 . H91 . 0.970(16) no
C10 . C11 . 1.389(2) yes
C10 . H101 . 0.962(17) no
C11 . C12 . 1.387(2) yes
C11 . C14 . 1.5045(19) yes
C12 . C13 . 1.383(2) yes
C12 . H121 . 0.958(17) no
C13 . H131 . 0.955(16) no
C14 . H142 . 0.97(2) no
C14 . H141 . 0.98(2) no
C14 . H143 . 0.93(2) no
C15 . C16 . 1.3882(17) yes
C15 . C22 . 1.4012(17) yes
C16 . C17 . 1.3815(18) yes
C16 . H161 . 0.950(16) no
C17 . C18 . 1.3855(18) yes
C17 . H171 . 0.952(16) no
C18 . O19 . 1.3626(15) yes
C18 . C21 . 1.3871(18) yes
O19 . C20 . 1.4255(17) yes
C20 . H201 . 0.97(2) no
C20 . H203 . 0.971(19) no
C20 . H202 . 1.007(19) no
C21 . C22 . 1.3745(18) yes
C21 . H211 . 0.917(17) no
C22 . H221 . 0.989(15) no
