Asymmetric assembly of pyrazole and 1,2,3-triazole with a methylene bridge: regioisomerism and energetic properties
Xiong, Jin; Cai, Jinxiong; Lai, Qi; Yin, Ping; Pang, Siping; Chemical Communications  (2022) –; doi:10.1039/D2CC02412H

data_7130629
_publ_section_title
;
 Asymmetric assembly of pyrazole and 1,2,3-triazole with a methylene
 bridge: regioisomerism and energetic properties
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02412H
_journal_year                    2022
_chemical_formula_moiety         'C6 H6 N10 O6'
_chemical_formula_sum            'C6 H6 N10 O6'
_chemical_formula_weight         314.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-09 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.353(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1538(11)
_cell_length_b                   8.2580(14)
_cell_length_c                   19.830(3)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.352
_cell_measurement_theta_min      2.952
_cell_volume                     1166.4(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8551
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_min         2.063
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0663 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8047. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0715
_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/[\s^2^(Fo^2^)+(0.0588P)^2^+2.6504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1701
_reflns_number_total             2352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02412h2.cif
_cod_data_source_block           mo_2022430_0m
_cod_database_code               7130629
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N9-H9B = N9-H9A
 0.87 with sigma of 0.02
3.a Rotating group:
 N9(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'