#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/15/7001548.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_7001548
loop_
_publ_author_name
'Ballesteros-Garrido, Rafael'
'Bonnafoux, Laurence'
'Leroux, Frédéric R.'
'Abarca, Belén'
'Colobert, Françoise'
_publ_section_title
;
 The [1,2,3]Triazolo[1,5-a]pyridine ring: A sensitive sensor for the
 electronic profile of phosphorus substituents
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              5068
_journal_page_last               5070
_journal_paper_doi               10.1039/b906034k
_journal_year                    2009
_chemical_formula_moiety         'C23 H17 N4 P'
_chemical_formula_sum            'C23 H17 N4 P'
_chemical_formula_weight         380.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3540(8)
_cell_length_b                   14.4253(4)
_cell_length_c                   19.6452(10)
_cell_measurement_reflns_used    8814
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3784.4(3)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16637
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.0064(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0964P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1781
_reflns_number_gt                2533
_reflns_number_total             4321
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b906034k.txt
_cod_data_source_block           colo29
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               7001548
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2917(2) 0.3962(2) 0.63462(15) 0.0445(7) Uani 1 1 d . . .
H1 H 0.2829 0.4109 0.6814 0.053 Uiso 1 1 calc R . .
C2 C 0.2707(2) 0.31117(19) 0.61084(15) 0.0459(8) Uani 1 1 d . . .
H2 H 0.2462 0.2652 0.6412 0.055 Uiso 1 1 calc R . .
C3 C 0.2843(2) 0.28902(18) 0.54184(15) 0.0422(7) Uani 1 1 d . . .
H3 H 0.2695 0.2282 0.5262 0.051 Uiso 1 1 calc R . .
C4 C 0.3184(2) 0.35348(16) 0.49725(14) 0.0350(7) Uani 1 1 d . . .
H4 H 0.3280 0.3383 0.4507 0.042 Uiso 1 1 calc R . .
C5 C 0.33937(19) 0.44364(16) 0.52139(13) 0.0300(6) Uani 1 1 d . . .
C6 C 0.3724(2) 0.52895(16) 0.49557(13) 0.0306(6) Uani 1 1 d . . .
C7 C 0.3990(2) 0.55390(16) 0.42598(13) 0.0288(6) Uani 1 1 d . . .
C8 C 0.4414(2) 0.63897(16) 0.40926(14) 0.0354(7) Uani 1 1 d . . .
H8 H 0.4536 0.6842 0.4434 0.042 Uiso 1 1 calc R . .
C9 C 0.4653(2) 0.65633(17) 0.34235(15) 0.0402(7) Uani 1 1 d . . .
H9 H 0.4940 0.7141 0.3298 0.048 Uiso 1 1 calc R . .
C10 C 0.4473(2) 0.58907(16) 0.29312(15) 0.0375(7) Uani 1 1 d . . .
H10 H 0.4648 0.5995 0.2469 0.045 Uiso 1 1 calc R . .
C11 C 0.4029(2) 0.50588(16) 0.31341(13) 0.0312(6) Uani 1 1 d . . .
C12 C 0.3848(2) 0.31085(16) 0.30077(13) 0.0306(6) Uani 1 1 d . . .
C13 C 0.3125(2) 0.24143(17) 0.30123(13) 0.0380(7) Uani 1 1 d . . .
H13 H 0.2513 0.2502 0.2773 0.046 Uiso 1 1 calc R . .
C14 C 0.3294(3) 0.15884(18) 0.33672(14) 0.0446(8) Uani 1 1 d . . .
H14 H 0.2805 0.1110 0.3359 0.054 Uiso 1 1 calc R . .
C15 C 0.4170(3) 0.14667(17) 0.37289(14) 0.0419(8) Uani 1 1 d . . .
H15 H 0.4282 0.0906 0.3970 0.050 Uiso 1 1 calc R . .
C16 C 0.4882(2) 0.21564(17) 0.37407(14) 0.0400(7) Uani 1 1 d . . .
H16 H 0.5479 0.2075 0.3997 0.048 Uiso 1 1 calc R . .
C17 C 0.4731(2) 0.29699(16) 0.33797(14) 0.0347(7) Uani 1 1 d . . .
H17 H 0.5232 0.3438 0.3384 0.042 Uiso 1 1 calc R . .
C18 C 0.4487(2) 0.41595(15) 0.18499(13) 0.0307(6) Uani 1 1 d . . .
C19 C 0.4092(2) 0.40861(17) 0.11937(13) 0.0356(7) Uani 1 1 d . . .
H19 H 0.3387 0.4095 0.1131 0.043 Uiso 1 1 calc R . .
C20 C 0.4709(2) 0.40008(19) 0.06368(15) 0.0428(7) Uani 1 1 d . . .
H20 H 0.4428 0.3948 0.0194 0.051 Uiso 1 1 calc R . .
C21 C 0.5739(2) 0.39922(17) 0.07201(15) 0.0408(7) Uani 1 1 d . . .
H21 H 0.6164 0.3932 0.0335 0.049 Uiso 1 1 calc R . .
C22 C 0.6144(2) 0.40708(16) 0.13581(15) 0.0373(7) Uani 1 1 d . . .
H22 H 0.6851 0.4067 0.1414 0.045 Uiso 1 1 calc R . .
C23 C 0.5524(2) 0.41566(16) 0.19283(14) 0.0345(7) Uani 1 1 d . . .
H23 H 0.5810 0.4213 0.2369 0.041 Uiso 1 1 calc R . .
N1 N 0.32636(18) 0.46137(14) 0.58918(11) 0.0346(5) Uani 1 1 d . . .
N2 N 0.35066(19) 0.55064(16) 0.60527(12) 0.0412(6) Uani 1 1 d . . .
N3 N 0.37766(17) 0.59021(14) 0.54793(12) 0.0367(6) Uani 1 1 d . . .
N4 N 0.37844(17) 0.48871(13) 0.37881(10) 0.0293(5) Uani 1 1 d . . .
P1 P 0.35641(6) 0.41764(4) 0.25394(3) 0.0322(2) Uani 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 0.0033 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'
P P 0.1023 0.0942 '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
C2 C1 N1 117.9(3) . . ?
C2 C1 H1 121.0 . . ?
N1 C1 H1 121.0 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C6 103.2(2) . . ?
N1 C5 C4 118.3(2) . . ?
C6 C5 C4 138.5(2) . . ?
N3 C6 C5 108.3(2) . . ?
N3 C6 C7 122.5(2) . . ?
C5 C6 C7 129.2(2) . . ?
N4 C7 C8 122.4(2) . . ?
N4 C7 C6 115.0(2) . . ?
C8 C7 C6 122.6(2) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
N4 C11 C10 122.2(2) . . ?
N4 C11 P1 113.37(18) . . ?
C10 C11 P1 123.9(2) . . ?
C13 C12 C17 118.6(2) . . ?
C13 C12 P1 117.6(2) . . ?
C17 C12 P1 123.75(19) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C23 C18 C19 118.5(3) . . ?
C23 C18 P1 125.9(2) . . ?
C19 C18 P1 115.5(2) . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.0(3) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N2 N1 C5 111.8(2) . . ?
N2 N1 C1 125.0(2) . . ?
C5 N1 C1 123.1(2) . . ?
N3 N2 N1 106.1(2) . . ?
N2 N3 C6 110.6(2) . . ?
C7 N4 C11 118.5(2) . . ?
C18 P1 C12 102.74(11) . . ?
C18 P1 C11 104.60(12) . . ?
C12 P1 C11 101.13(11) . . ?
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
C1 C2 1.342(4) . ?
C1 N1 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.405(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.367(3) . ?
C5 C6 1.402(3) . ?
C6 N3 1.358(3) . ?
C6 C7 1.458(4) . ?
C7 N4 1.348(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(3) . ?
C10 H10 0.9500 . ?
C11 N4 1.349(3) . ?
C11 P1 1.836(3) . ?
C12 C13 1.392(4) . ?
C12 C17 1.401(4) . ?
C12 P1 1.834(3) . ?
C13 C14 1.399(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.394(4) . ?
C18 C19 1.397(4) . ?
C18 P1 1.831(3) . ?
C19 C20 1.374(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N1 N2 1.365(3) . ?
N2 N3 1.313(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 N1 1.4(4) . . . . ?
C3 C4 C5 C6 -178.6(3) . . . . ?
N1 C5 C6 N3 0.5(3) . . . . ?
C4 C5 C6 N3 -179.6(3) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
N3 C6 C7 N4 -172.5(2) . . . . ?
C5 C6 C7 N4 8.1(4) . . . . ?
N3 C6 C7 C8 6.8(4) . . . . ?
C5 C6 C7 C8 -172.6(3) . . . . ?
N4 C7 C8 C9 -1.5(4) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 1.4(4) . . . . ?
C9 C10 C11 N4 -0.8(4) . . . . ?
C9 C10 C11 P1 170.2(2) . . . . ?
C17 C12 C13 C14 -1.7(4) . . . . ?
P1 C12 C13 C14 -179.3(2) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 C12 1.0(4) . . . . ?
C13 C12 C17 C16 0.4(4) . . . . ?
P1 C12 C17 C16 177.8(2) . . . . ?
C23 C18 C19 C20 0.8(4) . . . . ?
P1 C18 C19 C20 -175.4(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C19 C18 C23 C22 -0.7(3) . . . . ?
P1 C18 C23 C22 175.05(18) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C6 C5 N1 N2 -0.8(3) . . . . ?
C4 C5 N1 N2 179.2(2) . . . . ?
C6 C5 N1 C1 178.4(2) . . . . ?
C4 C5 N1 C1 -1.5(4) . . . . ?
C2 C1 N1 N2 179.8(3) . . . . ?
C2 C1 N1 C5 0.6(4) . . . . ?
C5 N1 N2 N3 0.9(3) . . . . ?
C1 N1 N2 N3 -178.4(3) . . . . ?
N1 N2 N3 C6 -0.6(3) . . . . ?
C5 C6 N3 N2 0.1(3) . . . . ?
C7 C6 N3 N2 -179.4(2) . . . . ?
C8 C7 N4 C11 2.1(4) . . . . ?
C6 C7 N4 C11 -178.6(2) . . . . ?
C10 C11 N4 C7 -0.9(4) . . . . ?
P1 C11 N4 C7 -172.77(18) . . . . ?
C23 C18 P1 C12 -60.1(2) . . . . ?
C19 C18 P1 C12 115.75(19) . . . . ?
C23 C18 P1 C11 45.1(2) . . . . ?
C19 C18 P1 C11 -138.98(18) . . . . ?
C13 C12 P1 C18 -114.6(2) . . . . ?
C17 C12 P1 C18 67.9(2) . . . . ?
C13 C12 P1 C11 137.4(2) . . . . ?
C17 C12 P1 C11 -40.0(3) . . . . ?
N4 C11 P1 C18 -149.50(19) . . . . ?
C10 C11 P1 C18 38.8(3) . . . . ?
N4 C11 P1 C12 -43.0(2) . . . . ?
C10 C11 P1 C12 145.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652602
