#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020091.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_4020091
loop_
_publ_author_name
'Unciti-Broceta, A.'
'Pineda-de-las-Infantas, M.J.'
'Díaz-Mochón, J.J.'
'Romagnoli, R.'
'Baraldi, P.G.'
'Gallo, M.A.'
'Espinosa, A.'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2878
_journal_page_last               2880
_journal_paper_doi               10.1021/jo0478398
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C11 H8 Cl N5'
_chemical_formula_weight         245.67
_chemical_melting_point          210
_chemical_name_systematic
;
 6-chloro-9-cyclopropylpyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.8420(10)
_cell_angle_beta                 106.8310(10)
_cell_angle_gamma                97.8980(10)
_cell_formula_units_Z            8
_cell_length_a                   9.9826(9)
_cell_length_b                   14.2394(13)
_cell_length_c                   15.8551(14)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     2074.1(3)
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ/ω 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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23004
_diffrn_reflns_theta_max         28.14
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         9218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+2.2919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                6703
_reflns_number_total             9218
_reflns_threshold_expression     >2sigma(I)
_cod_database_code               4020091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C63 C 0.1758(4) -0.0020(3) -0.0668(2) 0.0336(8) Uani 1 1 d . . .
Cl1 Cl -0.10704(8) 0.29242(6) 0.48317(5) 0.02875(19) Uani 1 1 d . . .
N3 N 0.0439(3) 0.16572(18) 0.53393(17) 0.0230(5) Uani 1 1 d . . .
N4 N 0.1738(3) 0.08928(18) 0.74930(17) 0.0233(5) Uani 1 1 d . . .
N13 N -0.0796(3) 0.32817(19) 0.68937(17) 0.0261(6) Uani 1 1 d . . .
N18 N 0.0401(3) 0.20920(18) 0.71303(16) 0.0219(5) Uani 1 1 d . . .
C22 C 0.1115(3) 0.1354(2) 0.6878(2) 0.0213(6) Uani 1 1 d . . .
C23 C -0.0199(3) 0.2321(2) 0.5606(2) 0.0229(6) Uani 1 1 d . . .
C26 C -0.0243(3) 0.2597(2) 0.6514(2) 0.0227(6) Uani 1 1 d . . .
C30 C 0.0188(3) 0.2513(2) 0.7927(2) 0.0241(7) Uani 1 1 d . . .
C31 C 0.1115(3) 0.1169(2) 0.5974(2) 0.0215(6) Uani 1 1 d . . .
C32 C 0.1848(3) 0.0453(2) 0.5718(2) 0.0226(6) Uani 1 1 d . . .
N36 N -0.0524(3) 0.3221(2) 0.77873(18) 0.0290(6) Uani 1 1 d . . .
C39 C 0.2520(3) -0.0023(2) 0.6350(2) 0.0251(7) Uani 1 1 d . . .
C48 C -0.0442(4) 0.2102(3) 0.9289(2) 0.0323(8) Uani 1 1 d . . .
C52 C 0.2439(3) 0.0221(2) 0.7224(2) 0.0269(7) Uani 1 1 d . . .
C60 C 0.0635(4) 0.2224(3) 0.8786(2) 0.0286(7) Uani 1 1 d . . .
C61 C 0.0773(4) 0.2943(3) 0.9648(3) 0.0321(8) Uani 1 1 d . . .
Cl2 Cl 0.62660(8) 0.20936(6) 0.10263(5) 0.03001(19) Uani 1 1 d . . .
N1 N 0.4815(3) 0.34144(19) 0.13842(17) 0.0244(6) Uani 1 1 d . . .
N2 N 0.3260(3) 0.41199(18) 0.32134(16) 0.0229(5) Uani 1 1 d . . .
N7 N 0.5768(3) 0.17031(19) 0.27977(17) 0.0258(6) Uani 1 1 d . . .
N11 N 0.4613(2) 0.29238(17) 0.29795(16) 0.0194(5) Uani 1 1 d . . .
N15 N 0.5389(3) 0.17440(19) 0.35785(17) 0.0250(6) Uani 1 1 d . . .
C17 C 0.3386(3) 0.4625(2) 0.1608(2) 0.0245(7) Uani 1 1 d . . .
C20 C 0.3955(3) 0.3680(2) 0.2707(2) 0.0202(6) Uani 1 1 d . . .
C21 C 0.4076(3) 0.3896(2) 0.1898(2) 0.0225(6) Uani 1 1 d . . .
C25 C 0.5293(3) 0.2412(2) 0.2452(2) 0.0210(6) Uani 1 1 d . . .
C27 C 0.4710(3) 0.2471(2) 0.3687(2) 0.0219(6) Uani 1 1 d . . .
C35 C 0.5372(3) 0.2721(2) 0.1653(2) 0.0227(6) Uani 1 1 d . . .
C37 C 0.2616(3) 0.4813(2) 0.2909(2) 0.0250(7) Uani 1 1 d . . .
C46 C 0.5319(4) 0.2944(3) 0.5414(2) 0.0275(7) Uani 1 1 d . . .
C53 C 0.4230(3) 0.2776(2) 0.4473(2) 0.0232(6) Uani 1 1 d . . .
C57 C 0.2652(3) 0.5085(2) 0.2114(2) 0.0266(7) Uani 1 1 d . . .
C59 C 0.4121(4) 0.2071(3) 0.5060(2) 0.0279(7) Uani 1 1 d . . .
Cl3 Cl 0.84955(9) 0.41006(6) 0.04601(6) 0.0351(2) Uani 1 1 d . . .
N6 N 0.6965(3) 0.5399(2) 0.07178(18) 0.0281(6) Uani 1 1 d . . .
N10 N 0.8672(3) 0.4216(2) 0.24812(18) 0.0298(6) Uani 1 1 d . . .
N12 N 0.7453(3) 0.54107(19) 0.25523(17) 0.0251(6) Uani 1 1 d . . .
N14 N 0.6203(3) 0.66784(19) 0.27327(17) 0.0256(6) Uani 1 1 d . . .
N28 N 0.8535(3) 0.4444(2) 0.33324(18) 0.0298(6) Uani 1 1 d . . .
C38 C 0.7741(3) 0.4845(2) 0.1098(2) 0.0273(7) Uani 1 1 d . . .
C40 C 0.6653(3) 0.6068(2) 0.2186(2) 0.0225(6) Uani 1 1 d . . .
C42 C 0.8009(3) 0.4796(2) 0.2021(2) 0.0255(7) Uani 1 1 d . . .
C43 C 0.5601(3) 0.6662(2) 0.0890(2) 0.0278(7) Uani 1 1 d . . .
C45 C 0.7804(3) 0.5160(2) 0.3373(2) 0.0266(7) Uani 1 1 d . . .
C47 C 0.6847(4) 0.4896(3) 0.4639(2) 0.0337(8) Uani 1 1 d . . .
C50 C 0.6415(3) 0.6025(2) 0.1256(2) 0.0225(6) Uani 1 1 d . . .
C51 C 0.5095(4) 0.7287(2) 0.1439(2) 0.0295(7) Uani 1 1 d . . .
C56 C 0.8245(4) 0.5483(3) 0.5091(2) 0.0317(8) Uani 1 1 d . . .
C58 C 0.5425(3) 0.7276(2) 0.2351(2) 0.0274(7) Uani 1 1 d . . .
C62 C 0.7412(3) 0.5585(2) 0.4170(2) 0.0297(7) Uani 1 1 d . . .
Cl4 Cl 0.33650(9) -0.10236(6) 0.37206(6) 0.0319(2) Uani 1 1 d . . .
N5 N 0.2493(2) 0.04445(18) 0.17957(16) 0.0222(5) Uani 1 1 d . . .
N8 N 0.3764(3) -0.07273(19) 0.18953(17) 0.0261(6) Uani 1 1 d . . .
N9 N 0.1867(3) 0.03006(19) 0.33848(17) 0.0249(6) Uani 1 1 d . . .
N16 N 0.1289(3) 0.17484(19) 0.16387(17) 0.0240(6) Uani 1 1 d . . .
C19 C 0.2677(3) -0.0218(2) 0.3107(2) 0.0242(7) Uani 1 1 d . . .
C24 C 0.1368(3) 0.0973(2) 0.28865(19) 0.0206(6) Uani 1 1 d . . .
C29 C 0.0530(3) 0.1582(2) 0.3187(2) 0.0261(7) Uani 1 1 d . . .
C33 C 0.1685(3) 0.1086(2) 0.21031(19) 0.0214(6) Uani 1 1 d . . .
N34 N 0.3684(3) -0.0441(2) 0.11024(18) 0.0284(6) Uani 1 1 d . . .
C41 C 0.0486(3) 0.2325(2) 0.1952(2) 0.0265(7) Uani 1 1 d . . .
C44 C 0.3037(3) -0.0193(2) 0.2294(2) 0.0229(6) Uani 1 1 d . . .
C49 C 0.3232(4) 0.0521(3) -0.0448(2) 0.0319(8) Uani 1 1 d . . .
C54 C 0.2924(3) 0.0249(2) 0.1042(2) 0.0242(7) Uani 1 1 d . . .
C55 C 0.0084(3) 0.2260(2) 0.2711(2) 0.0274(7) Uani 1 1 d . . .
C64 C 0.2508(3) 0.0682(3) 0.0260(2) 0.0278(7) Uani 1 1 d . . .
H2 H 0.212(3) 0.512(2) 0.3270(19) 0.015(7) Uiso 1 1 d . . .
H3 H 0.286(3) -0.013(2) 0.766(2) 0.022(8) Uiso 1 1 d . . .
H4 H 0.530(3) 0.348(2) 0.586(2) 0.023(8) Uiso 1 1 d . . .
H5 H 0.345(3) 0.479(2) 0.107(2) 0.030(9) Uiso 1 1 d . . .
H6 H 0.186(3) 0.035(2) 0.511(2) 0.019(8) Uiso 1 1 d . . .
H7 H 0.677(3) 0.428(2) 0.439(2) 0.013(7) Uiso 1 1 d . . .
H8 H 0.021(3) 0.282(2) 0.160(2) 0.024(8) Uiso 1 1 d . . .
H9 H 0.515(3) 0.772(2) 0.275(2) 0.023(8) Uiso 1 1 d . . .
H10 H 0.298(3) -0.052(2) 0.619(2) 0.024(8) Uiso 1 1 d . . .
H11 H 0.902(3) 0.515(2) 0.513(2) 0.023(8) Uiso 1 1 d . . .
H12 H 0.359(3) 0.323(2) 0.440(2) 0.019(8) Uiso 1 1 d . . .
H13 H -0.048(3) 0.267(2) 0.286(2) 0.020(8) Uiso 1 1 d . . .
H14 H 0.835(3) 0.602(2) 0.562(2) 0.028(9) Uiso 1 1 d . . .
H15 H 0.033(4) 0.150(2) 0.368(2) 0.037(10) Uiso 1 1 d . . .
H16 H -0.044(4) 0.156(3) 0.957(2) 0.032(9) Uiso 1 1 d . . .
H17 H -0.134(3) 0.224(2) 0.900(2) 0.021(8) Uiso 1 1 d . . .
H18 H 0.538(3) 0.664(2) 0.023(2) 0.029(9) Uiso 1 1 d . . .
H19 H 0.620(4) 0.287(2) 0.543(2) 0.035(10) Uiso 1 1 d . . .
H20 H 0.212(4) 0.127(3) 0.034(2) 0.035(10) Uiso 1 1 d . . .
H21 H 0.606(4) 0.508(3) 0.486(2) 0.043(11) Uiso 1 1 d . . .
H22 H 0.120(4) 0.180(3) 0.881(2) 0.034(10) Uiso 1 1 d . . .
H23 H 0.054(3) 0.353(3) 0.958(2) 0.028(9) Uiso 1 1 d . . .
H24 H 0.439(4) 0.144(3) 0.487(2) 0.034(9) Uiso 1 1 d . . .
H25 H 0.386(4) 0.018(2) -0.038(2) 0.028(9) Uiso 1 1 d . . .
H26 H 0.224(3) 0.558(2) 0.197(2) 0.029(9) Uiso 1 1 d . . .
H27 H 0.687(4) 0.617(3) 0.395(3) 0.051(11) Uiso 1 1 d . . .
H28 H 0.094(4) 0.017(3) -0.106(3) 0.046(11) Uiso 1 1 d . . .
H29 H 0.162(4) -0.071(3) -0.064(2) 0.038(10) Uiso 1 1 d . . .
H30 H 0.461(4) 0.774(3) 0.121(3) 0.050(11) Uiso 1 1 d . . .
H31 H 0.143(4) 0.292(3) 1.008(3) 0.034(11) Uiso 1 1 d . . .
H32 H 0.339(4) 0.210(3) 0.529(3) 0.050(11) Uiso 1 1 d . . .
H33 H 0.341(4) 0.107(3) -0.076(3) 0.062(13) Uiso 1 1 d . . .
