#------------------------------------------------------------------------------
#$Date: 2022-09-03 00:54:22 +0300 (Sat, 03 Sep 2022) $
#$Revision: 277600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130628.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_7130628
loop_
_publ_author_name
'Xiong, Jin'
'Cai, Jinxiong'
'Lai, Qi'
'Yin, Ping'
'Pang, Siping'
_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_block_doi                 10.5517/ccdc.csd.cc2c8g04
_audit_creation_date             2022-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.253(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1738(8)
_cell_length_b                   8.3136(10)
_cell_length_c                   19.948(3)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.834
_cell_measurement_theta_min      3.117
_cell_volume                     1184.7(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      298
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8693
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.050
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1055 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.8450. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0704
_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)+(0.0749P)²+1.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1323
_reflns_number_total             2689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02412h2.cif
_cod_data_source_block           MPT-2-rt
_cod_original_cell_volume        1184.7(2)
_cod_database_code               7130628
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.b X=CH2 refined with riding coordinates:
 N10(H10A,H10B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N4 N 0.4827(4) 0.3656(4) 0.20230(16) 0.0439(8) Uani 1 1 d . . . . .
N6 N 0.4431(5) 0.3836(4) 0.31889(17) 0.0486(9) Uani 1 1 d . . . . .
O3 O 0.1952(4) 0.6528(4) 0.07252(17) 0.0716(10) Uani 1 1 d . . . . .
N3 N 0.3607(4) 0.4587(4) 0.16708(17) 0.0477(9) Uani 1 1 d . . . . .
O2 O 0.9698(4) 0.3366(4) 0.18750(18) 0.0725(10) Uani 1 1 d . . . . .
N7 N 0.3004(5) 0.4620(5) 0.33934(17) 0.0509(9) Uani 1 1 d . . . . .
N5 N 0.8178(5) 0.2952(5) 0.2083(2) 0.0555(10) Uani 1 1 d . . . . .
O1 O 0.8032(5) 0.1881(5) 0.24966(19) 0.0809(11) Uani 1 1 d . . . . .
O5 O 0.1057(5) 0.6520(5) 0.41675(18) 0.0781(11) Uani 1 1 d . . . . .
O6 O 0.3653(5) 0.7403(5) 0.46834(18) 0.0775(10) Uani 1 1 d . . . . .
N8 N 0.6117(5) 0.4116(5) 0.35200(18) 0.0547(10) Uani 1 1 d . . . . .
N2 N 0.7828(5) 0.5331(5) 0.0891(2) 0.0594(11) Uani 1 1 d D . . . .
N9 N 0.2751(6) 0.6518(5) 0.4275(2) 0.0602(10) Uani 1 1 d . . . . .
N1 N 0.3642(5) 0.6349(5) 0.07436(19) 0.0596(10) Uani 1 1 d . . . . .
C3 C 0.6579(5) 0.3792(5) 0.17954(19) 0.0412(9) Uani 1 1 d . . . . .
N10 N 0.7048(5) 0.5821(5) 0.4435(2) 0.0703(12) Uani 1 1 d . . . . .
H10A H 0.819694 0.552585 0.443433 0.084 Uiso 1 1 calc R . . . .
H10B H 0.673653 0.651577 0.472369 0.084 Uiso 1 1 calc R . . . .
C1 C 0.4578(5) 0.5287(5) 0.1218(2) 0.0460(10) Uani 1 1 d . . . . .
C5 C 0.3820(5) 0.5463(5) 0.3902(2) 0.0458(10) Uani 1 1 d . . . . .
C2 C 0.6478(5) 0.4860(5) 0.12679(19) 0.0438(10) Uani 1 1 d . . . . .
C4 C 0.4189(6) 0.2841(5) 0.2601(2) 0.0486(11) Uani 1 1 d . . . . .
H4A H 0.287674 0.256593 0.251001 0.058 Uiso 1 1 calc R . . . .
H4B H 0.488910 0.185088 0.268184 0.058 Uiso 1 1 calc R . . . .
O4 O 0.4608(5) 0.7037(5) 0.0361(2) 0.1006(15) Uani 1 1 d . . . . .
C6 C 0.5752(6) 0.5203(6) 0.3987(2) 0.0505(11) Uani 1 1 d . . . . .
H2A H 0.746(6) 0.590(5) 0.0547(16) 0.065(15) Uiso 1 1 d D . . . .
H2B H 0.896(3) 0.507(5) 0.1029(19) 0.050(13) Uiso 1 1 d D . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N4 C3 110.9(3) . . ?
N3 N4 C4 117.1(3) . . ?
C3 N4 C4 131.6(3) . . ?
N7 N6 N8 117.0(3) . . ?
N7 N6 C4 120.2(3) . . ?
N8 N6 C4 122.6(3) . . ?
N4 N3 C1 104.8(3) . . ?
N6 N7 C5 101.5(3) . . ?
O2 N5 C3 115.4(4) . . ?
O1 N5 O2 123.7(4) . . ?
O1 N5 C3 121.0(4) . . ?
C6 N8 N6 103.5(3) . . ?
C2 N2 H2A 115(3) . . ?
C2 N2 H2B 117(3) . . ?
H2A N2 H2B 128(4) . . ?
O5 N9 O6 124.8(4) . . ?
O5 N9 C5 119.2(4) . . ?
O6 N9 C5 115.9(4) . . ?
O3 N1 C1 120.3(4) . . ?
O3 N1 O4 123.0(4) . . ?
O4 N1 C1 116.6(4) . . ?
N4 C3 N5 123.7(4) . . ?
C2 C3 N4 108.6(3) . . ?
C2 C3 N5 127.7(4) . . ?
H10A N10 H10B 120.0 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
N3 C1 N1 118.8(4) . . ?
N3 C1 C2 114.2(4) . . ?
C2 C1 N1 127.0(4) . . ?
N7 C5 N9 120.4(4) . . ?
N7 C5 C6 112.0(4) . . ?
C6 C5 N9 127.6(4) . . ?
N2 C2 C3 129.0(4) . . ?
N2 C2 C1 129.4(4) . . ?
C3 C2 C1 101.5(3) . . ?
N4 C4 H4A 109.4 . . ?
N4 C4 H4B 109.4 . . ?
N6 C4 N4 111.0(3) . . ?
N6 C4 H4A 109.4 . . ?
N6 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N8 C6 C5 105.9(4) . . ?
N10 C6 N8 123.8(4) . . ?
N10 C6 C5 130.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 N3 1.321(4) . ?
N4 C3 1.380(5) . ?
N4 C4 1.447(5) . ?
N6 N7 1.310(4) . ?
N6 N8 1.345(5) . ?
N6 C4 1.432(5) . ?
O3 N1 1.218(4) . ?
N3 C1 1.324(5) . ?
O2 N5 1.249(4) . ?
N7 C5 1.325(5) . ?
N5 O1 1.225(5) . ?
N5 C3 1.418(5) . ?
O5 N9 1.214(5) . ?
O6 N9 1.236(5) . ?
N8 C6 1.341(6) . ?
N2 C2 1.338(5) . ?
N2 H2A 0.854(19) . ?
N2 H2B 0.860(19) . ?
N9 C5 1.419(6) . ?
N1 C1 1.419(5) . ?
N1 O4 1.219(5) . ?
C3 C2 1.374(5) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C6 1.331(5) . ?
C1 C2 1.403(5) . ?
C5 C6 1.398(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
