#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:26:29 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/99/4349922.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_4349922
loop_
_publ_author_name
'Vismara, Rebecca'
'Tuci, Giulia'
'Mosca, Nello'
'Domasevitch, Kostiantyn V.'
'Di Nicola, Corrado'
'Pettinari, Claudio'
'Giambastiani, Giuliano'
'Galli, Simona'
'Rossin, Andrea'
_publ_section_title
;
 Amino-decorated bis(pyrazolate) metal--organic frameworks for carbon
 dioxide capture and green conversion into cyclic carbonates
;
_journal_issue                   2
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              533
_journal_paper_doi               10.1039/C8QI00997J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C6 H7 N5'
_chemical_formula_weight         149.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-09-06 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.583(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1099(9)
_cell_length_b                   4.5429(4)
_cell_length_c                   9.3940(12)
_cell_measurement_reflns_used    2608
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      27.861
_cell_measurement_theta_min      2.635
_cell_volume                     329.93(7)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'Diamond 2.1e (Brandenburg, 1999)'
_computing_publication_material  'WinGX 1.70.01 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe Image Plate Diffraction System'
_diffrn_measurement_method       'φ oscillation scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2608
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.861
_diffrn_reflns_theta_min         2.635
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.8982
_exptl_absorpt_correction_T_min  0.8508
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'X-RED (Stoe & Cie, 2001) and X-SHAPE (Stoe & Cie, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       prism
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1416
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0352
_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)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.839
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                1029
_reflns_number_total             1416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qi00997j2.cif
_cod_data_source_block           H2BPZNH2
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4349922
_shelx_shelxl_version_number     2014/7
_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_min   0.971
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 -0.2179(4) -0.0123(10) 0.4662(4) 0.0293(8) Uani 1 1 d . . . A 1
H1N H -0.2781 -0.1268 0.3951 0.044 Uiso 1 1 calc R U . A 1
N2 N -0.2893(5) 0.1829(8) 0.5428(4) 0.0309(10) Uani 1 1 d . . . A 1
N3 N 0.4081(4) 0.5020(10) 0.8655(4) 0.0315(9) Uani 1 1 d . . . A 1
H2N H 0.4708 0.6159 0.9355 0.047 Uiso 1 1 calc R U . A 1
N4 N 0.4733(4) 0.3147(9) 0.7881(4) 0.0297(10) Uani 1 1 d . . . A 1
N5 N -0.1729(7) 0.5086(12) 0.7394(6) 0.0293(11) Uani 0.77 1 d . . P A 1
H3N H -0.1157 0.6648 0.7403 0.044 Uiso 1 1 d R U . A 1
H4N H -0.2827 0.5607 0.7237 0.044 Uiso 1 1 d R U . A 1
C1 C -0.0457(5) -0.0054(11) 0.5137(5) 0.0280(10) Uani 1 1 d . . . A 1
H1 H 0.0282 -0.1216 0.4768 0.034 Uiso 1 1 calc R U . A 1
C2 C 0.0060(5) 0.2006(9) 0.6260(5) 0.0201(9) Uani 1 1 d . . . A 1
C3 C -0.1532(5) 0.3135(8) 0.6385(4) 0.0242(10) Uani 1 1 d . . . A 1
C4 C 0.2339(4) 0.4953(12) 0.8233(5) 0.0282(9) Uani 1 1 d . . . A 1
H4 H 0.1618 0.6101 0.8629 0.034 Uiso 1 1 calc R U . A 1
C5 C 0.1809(5) 0.2876(10) 0.7106(5) 0.0246(10) Uani 1 1 d . . . A 1
C6 C 0.3360(5) 0.1870(9) 0.6933(4) 0.0277(11) Uani 1 1 d . . . A 1
H6 H 0.3428 0.0448 0.6226 0.033 Uiso 1 1 calc R U . A 1
N5A N 0.364(2) -0.009(4) 0.5912(19) 0.030(4) Uiso 0.23 1 d . . P B 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 112.0(4)
C1 N1 H1N 124.0
N2 N1 H1N 124.0
C3 N2 N1 104.2(4)
N4 N3 C4 112.3(4)
N4 N3 H2N 123.8
C4 N3 H2N 123.8
N3 N4 C6 104.7(3)
C3 N5 H3N 112.3
C3 N5 H4N 112.7
H3N N5 H4N 107.3
N1 C1 C2 108.6(4)
N1 C1 H1 125.7
C2 C1 H1 125.7
C1 C2 C3 103.5(3)
C1 C2 C5 128.6(3)
C3 C2 C5 127.9(3)
N2 C3 N5 121.3(4)
N2 C3 C2 111.7(3)
N5 C3 C2 126.8(4)
N3 C4 C5 107.2(4)
N3 C4 H4 126.4
C5 C4 H4 126.4
C4 C5 C6 103.3(4)
C4 C5 C2 128.9(3)
C6 C5 C2 127.7(3)
N4 C6 C5 112.4(4)
N4 C6 H6 123.8
C5 C6 H6 123.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.332(4)
N1 N2 1.375(6)
N1 H1N 0.8700
N2 C3 1.334(5)
N3 N4 1.329(5)
N3 C4 1.348(4)
N3 H2N 0.8700
N4 C6 1.331(5)
N5 C3 1.342(6)
N5 H3N 0.8462
N5 H4N 0.8898
C1 C2 1.377(7)
C1 H1 0.9400
C2 C3 1.426(5)
C2 C5 1.456(3)
C4 C5 1.385(7)
C4 H4 0.9400
C5 C6 1.393(6)
C6 H6 0.9400
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 N1 N2 C3 0.8(4)
C4 N3 N4 C6 0.4(5)
N2 N1 C1 C2 -0.3(5)
N1 C1 C2 C3 -0.3(5)
N1 C1 C2 C5 -179.3(3)
N1 N2 C3 N5 -176.1(4)
N1 N2 C3 C2 -1.0(4)
C1 C2 C3 N2 0.8(5)
C5 C2 C3 N2 179.8(3)
C1 C2 C3 N5 175.5(5)
C5 C2 C3 N5 -5.4(6)
N4 N3 C4 C5 0.3(5)
N3 C4 C5 C6 -0.9(5)
N3 C4 C5 C2 -178.9(3)
C1 C2 C5 C4 179.7(7)
C3 C2 C5 C4 0.9(5)
C1 C2 C5 C6 2.2(5)
C3 C2 C5 C6 -176.6(6)
N3 N4 C6 C5 -1.0(5)
C4 C5 C6 N4 1.2(5)
C2 C5 C6 N4 179.3(3)
