#------------------------------------------------------------------------------
#$Date: 2022-09-03 00:54:22 +0300 (Sat, 03 Sep 2022) $
#$Revision: 277600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130631.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_7130631
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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-29 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2740(4)
_cell_length_b                   11.6263(7)
_cell_length_c                   15.6940(9)
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.672
_cell_measurement_theta_min      2.180
_cell_volume                     1144.77(12)
_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      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0723
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.180
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0869 before and 0.0725 after correction. The Ratio of minimum to maximum transmission is 0.9399. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0435
_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)+(0.0399P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2018
_reflns_number_total             2626
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02412h2.cif
_cod_data_source_block           mo_2022593_0m
_cod_database_code               7130631
_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   0.994
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00E,H00F)
2.b X=CH2 refined with riding coordinates:
 N00D(H00A,H00B), N00G(H00C,H00D)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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
O001 O 0.1574(3) -0.6721(2) -0.38690(15) 0.0260(6) Uani 1 1 d . . . . .
O002 O -0.9699(4) -0.4610(2) -0.79303(16) 0.0308(6) Uani 1 1 d . . . . .
O003 O -0.7072(4) -0.5837(2) -0.79116(16) 0.0320(6) Uani 1 1 d . . . . .
O004 O -0.1820(4) -0.6674(2) -0.35621(15) 0.0316(6) Uani 1 1 d . . . . .
N005 N -0.5036(4) -0.4537(2) -0.66715(17) 0.0204(6) Uani 1 1 d . . . . .
N006 N -0.7933(5) -0.4937(3) -0.76682(17) 0.0244(7) Uani 1 1 d . . . . .
N007 N -0.0308(4) -0.6535(2) -0.40635(17) 0.0219(6) Uani 1 1 d . . . . .
N008 N 0.0733(4) -0.5994(3) -0.54871(17) 0.0229(7) Uani 1 1 d . . . . .
N009 N -0.2365(4) -0.5726(2) -0.60488(16) 0.0207(6) Uani 1 1 d . . . . .
O00A O -0.7027(5) -0.1114(2) -0.58856(19) 0.0457(8) Uani 1 1 d . . . . .
N00B N -0.0185(4) -0.5730(3) -0.61971(17) 0.0245(7) Uani 1 1 d . . . . .
N00C N -0.4390(5) -0.3708(2) -0.61485(18) 0.0249(7) Uani 1 1 d . . . . .
N00D N -0.4732(4) -0.6075(3) -0.48921(18) 0.0249(7) Uani 1 1 d . . . . .
H00A H -0.586465 -0.594857 -0.520896 0.030 Uiso 1 1 calc R . . . .
H00B H -0.488010 -0.625555 -0.435071 0.030 Uiso 1 1 calc R . . . .
O00E O -0.4239(5) -0.1763(2) -0.52083(18) 0.0499(8) Uani 1 1 d . . . . .
N00F N -0.5681(6) -0.1863(3) -0.57293(19) 0.0349(8) Uani 1 1 d . . . . .
N00G N -0.9282(5) -0.2563(3) -0.6991(2) 0.0331(8) Uani 1 1 d . . . . .
H00C H -1.019549 -0.284508 -0.736181 0.040 Uiso 1 1 calc R . . . .
H00D H -0.950889 -0.188293 -0.676194 0.040 Uiso 1 1 calc R . . . .
C00H C -0.0788(5) -0.6169(3) -0.4889(2) 0.0197(7) Uani 1 1 d . . . . .
C00I C -0.2812(5) -0.5995(3) -0.5228(2) 0.0193(7) Uani 1 1 d . . . . .
C00J C -0.6922(5) -0.4248(3) -0.7067(2) 0.0201(7) Uani 1 1 d . . . . .
C00K C -0.5875(6) -0.2894(3) -0.6216(2) 0.0247(8) Uani 1 1 d . . . . .
C00L C -0.7548(6) -0.3168(3) -0.6776(2) 0.0235(8) Uani 1 1 d . . . . .
C00M C -0.3798(5) -0.5609(3) -0.6754(2) 0.0230(8) Uani 1 1 d . . . . .
H00E H -0.477946 -0.627519 -0.677123 0.028 Uiso 1 1 calc R . . . .
H00F H -0.297915 -0.559612 -0.729355 0.028 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N00C N005 C00J 111.3(3) . . ?
N00C N005 C00M 120.5(3) . . ?
C00J N005 C00M 128.2(3) . . ?
O002 N006 C00J 117.1(3) . . ?
O003 N006 O002 123.1(3) . . ?
O003 N006 C00J 119.8(3) . . ?
O001 N007 O004 123.3(3) . . ?
O001 N007 C00H 119.1(3) . . ?
O004 N007 C00H 117.6(3) . . ?
N00B N008 C00H 108.6(3) . . ?
N00B N009 C00M 119.3(3) . . ?
C00I N009 N00B 111.3(3) . . ?
C00I N009 C00M 128.8(3) . . ?
N008 N00B N009 107.2(3) . . ?
N005 N00C C00K 104.6(3) . . ?
O00A N00F C00K 115.3(3) . . ?
O00E N00F O00A 124.7(3) . . ?
O00E N00F C00K 120.1(3) . . ?
N008 C00H N007 122.5(3) . . ?
N008 C00H C00I 110.9(3) . . ?
C00I C00H N007 126.6(3) . . ?
N009 C00I C00H 102.0(3) . . ?
N00D C00I N009 125.9(3) . . ?
N00D C00I C00H 132.1(3) . . ?
N005 C00J N006 123.8(3) . . ?
N005 C00J C00L 108.3(3) . . ?
N006 C00J C00L 127.8(3) . . ?
N00C C00K N00F 119.6(3) . . ?
N00C C00K C00L 114.3(3) . . ?
C00L C00K N00F 126.1(3) . . ?
N00G C00L C00J 128.3(3) . . ?
N00G C00L C00K 130.2(3) . . ?
C00J C00L C00K 101.5(3) . . ?
N009 C00M N005 110.1(3) . . ?
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
O001 N007 1.239(3) . ?
O002 N006 1.241(4) . ?
O003 N006 1.238(4) . ?
O004 N007 1.243(3) . ?
N005 N00C 1.329(4) . ?
N005 C00J 1.378(4) . ?
N005 C00M 1.474(4) . ?
N006 C00J 1.391(4) . ?
N007 C00H 1.396(4) . ?
N008 N00B 1.291(4) . ?
N008 C00H 1.354(4) . ?
N009 N00B 1.387(4) . ?
N009 C00I 1.354(4) . ?
N009 C00M 1.433(4) . ?
O00A N00F 1.238(4) . ?
N00C C00K 1.332(4) . ?
N00D C00I 1.318(4) . ?
O00E N00F 1.225(4) . ?
N00F C00K 1.427(5) . ?
N00G C00L 1.339(4) . ?
C00H C00I 1.392(5) . ?
C00J C00L 1.393(5) . ?
C00K C00L 1.405(5) . ?
