#------------------------------------------------------------------------------
#$Date: 2017-05-31 05:05:50 +0300 (Wed, 31 May 2017) $
#$Revision: 197057 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/31/7043154.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_7043154
loop_
_publ_author_name
'Strohecker, Daniel'
'Lynch, Vincent'
'Holliday, Bradley'
'Jones, Richard A.'
_publ_section_title
;
 Synthesis and Electronic Investigation of Mono- and Di-substituted
 4-Nitro- and 4-Amino-bis(pyrazol-1-yl)pyridine-type Ligands and
 Luminescent Eu(III) Derivatives
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01153A
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N5'
_chemical_formula_sum            'C12 H11 N5'
_chemical_formula_weight         225.26
_chemical_melting_point          427(4)
_chemical_name_common            NH2-bppy
_chemical_name_systematic
2-(4-aminopyrazol-1-yl)-6-(pyrazol-1-yl)pyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-03-21 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.812(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9809(16)
_cell_length_b                   3.7881(3)
_cell_length_c                   12.2183(9)
_cell_measurement_reflns_used    1704
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      75.2
_cell_measurement_theta_min      4.01
_cell_volume                     1028.31(14)
_computing_cell_refinement
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_collection
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'Shelxl-2014/7, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2014/7, Sheldrick, G. M.'
_computing_structure_solution
;

SHELXT. Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. 
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5061
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.692
_diffrn_reflns_theta_min         3.979
_diffrn_source                   'sealed microfocus tube'
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       acicular
_exptl_crystal_F_000             472
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0670
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1350P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.2137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1624
_reflns_number_total             2060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01153a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '423.35 - 431.55' was changed to
'427(4)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7043154
_shelx_shelxl_version_number     2016/6
_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   0.875
_shelx_estimated_absorpt_t_max   0.956
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.68720(10) 0.5198(6) 0.33140(18) 0.0250(5) Uani 1 1 d . .
C2 C 0.68254(10) 0.6797(6) 0.43145(19) 0.0290(5) Uani 1 1 d . .
H2 H 0.644572 0.736473 0.444345 0.035 Uiso 1 1 calc R U
C3 C 0.73596(11) 0.7520(6) 0.51130(19) 0.0299(6) Uani 1 1 d . .
H3 H 0.734956 0.860252 0.580940 0.036 Uiso 1 1 calc R U
C4 C 0.79043(10) 0.6685(6) 0.49056(19) 0.0289(5) Uani 1 1 d . .
H4 H 0.827304 0.718957 0.544405 0.035 Uiso 1 1 calc R U
C5 C 0.78948(10) 0.5066(6) 0.38739(18) 0.0243(5) Uani 1 1 d . .
C6 C 0.63185(11) 0.2818(6) 0.1442(2) 0.0297(6) Uani 1 1 d . .
H6 H 0.664950 0.212957 0.115769 0.036 Uiso 1 1 calc R U
C7 C 0.57258(11) 0.2497(7) 0.0897(2) 0.0347(6) Uani 1 1 d . .
H7 H 0.555534 0.158334 0.016043 0.042 Uiso 1 1 calc R U
C8 C 0.54211(11) 0.3842(7) 0.1681(2) 0.0378(6) Uani 1 1 d . .
H8 H 0.499525 0.394316 0.153938 0.045 Uiso 1 1 calc R U
C9 C 0.85145(10) 0.2872(6) 0.26113(18) 0.0263(5) Uani 1 1 d . .
H9 H 0.821408 0.264917 0.191783 0.032 Uiso 1 1 calc R U
C10 C 0.91132(10) 0.2104(6) 0.27932(18) 0.0282(6) Uani 1 1 d . .
C11 C 0.93605(10) 0.2816(7) 0.39525(19) 0.0325(6) Uani 1 1 d . .
H11 H 0.977337 0.250142 0.432805 0.039 Uiso 1 1 calc R U
N1 N 0.57957(9) 0.4941(6) 0.26319(18) 0.0344(5) Uani 1 1 d . .
N2 N 0.63506(8) 0.4305(5) 0.24697(16) 0.0277(5) Uani 1 1 d . .
N3 N 0.73906(8) 0.4342(5) 0.30808(15) 0.0251(5) Uani 1 1 d . .
N4 N 0.84324(8) 0.4027(5) 0.36268(15) 0.0252(5) Uani 1 1 d . .
N5 N 0.89514(8) 0.3970(6) 0.44569(16) 0.0335(5) Uani 1 1 d . .
N6 N 0.94460(9) 0.1071(7) 0.20353(18) 0.0362(6) Uani 1 1 d . .
H6A H 0.9716(18) -0.069(12) 0.224(4) 0.084(14) Uiso 1 1 d . .
H6B H 0.9189(15) 0.083(10) 0.121(3) 0.067(11) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
N3 C1 C2 124.5(2)
N3 C1 N2 115.1(2)
C2 C1 N2 120.4(2)
C3 C2 C1 116.8(2)
C3 C2 H2 121.6
C1 C2 H2 121.6
C4 C3 C2 120.6(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 117.5(2)
C3 C4 H4 121.2
C5 C4 H4 121.2
N3 C5 C4 123.7(2)
N3 C5 N4 115.81(19)
C4 C5 N4 120.44(19)
C7 C6 N2 107.5(2)
C7 C6 H6 126.3
N2 C6 H6 126.3
C6 C7 C8 104.0(2)
C6 C7 H7 128.0
C8 C7 H7 128.0
N1 C8 C7 112.5(2)
N1 C8 H8 123.7
C7 C8 H8 123.7
C10 C9 N4 106.60(19)
C10 C9 H9 126.7
N4 C9 H9 126.7
C9 C10 N6 130.5(2)
C9 C10 C11 104.6(2)
N6 C10 C11 124.7(2)
N5 C11 C10 112.3(2)
N5 C11 H11 123.9
C10 C11 H11 123.9
C8 N1 N2 103.9(2)
C6 N2 N1 112.07(19)
C6 N2 C1 127.6(2)
N1 N2 C1 120.3(2)
C1 N3 C5 116.9(2)
N5 N4 C9 111.94(18)
N5 N4 C5 119.97(18)
C9 N4 C5 128.06(18)
C11 N5 N4 104.53(18)
C10 N6 H6A 119(3)
C10 N6 H6B 114(2)
H6A N6 H6B 113(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.334(3)
C1 C2 1.393(3)
C1 N2 1.408(3)
C2 C3 1.386(3)
C2 H2 0.9500
C3 C4 1.376(3)
C3 H3 0.9500
C4 C5 1.397(3)
C4 H4 0.9500
C5 N3 1.335(3)
C5 N4 1.401(3)
C6 C7 1.360(3)
C6 N2 1.361(3)
C6 H6 0.9500
C7 C8 1.418(4)
C7 H7 0.9500
C8 N1 1.324(3)
C8 H8 0.9500
C9 C10 1.368(3)
C9 N4 1.373(3)
C9 H9 0.9500
C10 N6 1.399(3)
C10 C11 1.411(3)
C11 N5 1.323(3)
C11 H11 0.9500
N1 N2 1.361(3)
N4 N5 1.354(2)
N6 H6A 0.90(4)
N6 H6B 1.04(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N6 0.90(4) 2.27(4) 3.144(3) 165(4) 2_745
N6 H6B N5 1.04(4) 2.07(4) 3.064(3) 160(3) 4_565
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
N3 C1 C2 C3 -0.1(4)
N2 C1 C2 C3 178.6(2)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 N3 1.0(3)
C3 C4 C5 N4 -177.6(2)
N2 C6 C7 C8 -0.8(3)
C6 C7 C8 N1 0.6(3)
N4 C9 C10 N6 -175.0(2)
N4 C9 C10 C11 1.0(3)
C9 C10 C11 N5 -0.6(3)
N6 C10 C11 N5 175.7(2)
C7 C8 N1 N2 -0.1(3)
C7 C6 N2 N1 0.9(3)
C7 C6 N2 C1 -178.7(2)
C8 N1 N2 C6 -0.5(3)
C8 N1 N2 C1 179.1(2)
N3 C1 N2 C6 -2.8(3)
C2 C1 N2 C6 178.4(2)
N3 C1 N2 N1 177.72(18)
C2 C1 N2 N1 -1.2(3)
C2 C1 N3 C5 0.5(3)
N2 C1 N3 C5 -178.34(17)
C4 C5 N3 C1 -0.9(3)
N4 C5 N3 C1 177.76(18)
C10 C9 N4 N5 -1.1(3)
C10 C9 N4 C5 -178.8(2)
N3 C5 N4 N5 -166.33(19)
C4 C5 N4 N5 12.4(3)
N3 C5 N4 C9 11.2(3)
C4 C5 N4 C9 -170.1(2)
C10 C11 N5 N4 -0.1(3)
C9 N4 N5 C11 0.8(3)
C5 N4 N5 C11 178.7(2)
