#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238009.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238009
loop_
_publ_author_name
'Bassoude, Ibtissam'
'Berteina-Raboin, Sabine'
'Essassi, El Mokhtar'
'Guillaumet, Gérald'
'El Ammari, Lahcen'
_publ_section_title
;
 7-Chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine
;
_journal_coeditor_code           RZ5056
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o749
_journal_paper_doi               10.1107/S1600536813009896
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H10 Cl N3'
_chemical_formula_moiety         'C13 H10 Cl N3'
_chemical_formula_sum            'C13 H10 Cl N3'
_chemical_formula_weight         243.69
_chemical_name_systematic
;
7-Chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 100.131(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5993(2)
_cell_length_b                   12.6166(4)
_cell_length_c                   13.8702(5)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.98
_cell_volume                     1136.84(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEXII area-detector'
_diffrn_measurement_method       'φ and 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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16957
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.311
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.2738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2521
_reflns_number_total             2925
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz5056.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238009
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.07651(19) 0.69856(10) 0.25074(9) 0.0344(3) Uani d . 1 1
C C2 -0.0283(2) 0.72024(10) 0.32394(10) 0.0393(3) Uani d . 1 1
H H2 -0.1459 0.7622 0.3121 0.047 Uiso calc R 1 1
C C3 0.0426(2) 0.67836(11) 0.41889(10) 0.0420(3) Uani d . 1 1
C C4 0.3143(2) 0.59912(10) 0.36620(9) 0.0369(3) Uani d . 1 1
C C5 0.4894(2) 0.54075(11) 0.36126(9) 0.0398(3) Uani d . 1 1
H H5 0.5708 0.5041 0.4120 0.048 Uiso calc R 1 1
C C6 0.51851(19) 0.54836(10) 0.26417(9) 0.0349(3) Uani d . 1 1
C C7 0.68242(19) 0.49912(10) 0.21982(9) 0.0353(3) Uani d . 1 1
C C8 0.8475(2) 0.44870(11) 0.27861(11) 0.0423(3) Uani d . 1 1
H H8 0.8546 0.4468 0.3462 0.051 Uiso calc R 1 1
C C9 1.0010(2) 0.40136(12) 0.23699(13) 0.0502(4) Uani d . 1 1
H H9 1.1112 0.3684 0.2768 0.060 Uiso calc R 1 1
C C10 0.9911(2) 0.40282(13) 0.13685(13) 0.0522(4) Uani d . 1 1
H H10 1.0940 0.3706 0.1092 0.063 Uiso calc R 1 1
C C11 0.8287(2) 0.45210(13) 0.07785(12) 0.0521(4) Uani d . 1 1
H H11 0.8215 0.4528 0.0103 0.063 Uiso calc R 1 1
C C12 0.6755(2) 0.50072(12) 0.11910(11) 0.0448(3) Uani d . 1 1
H H12 0.5671 0.5347 0.0789 0.054 Uiso calc R 1 1
C C13 -0.0778(3) 0.69939(16) 0.49944(12) 0.0599(4) Uani d . 1 1
H H13A -0.1946 0.7430 0.4748 0.090 Uiso calc R 1 1
H H13B 0.0084 0.7352 0.5525 0.090 Uiso calc R 1 1
H H13C -0.1239 0.6334 0.5224 0.090 Uiso calc R 1 1
N N1 0.24981(16) 0.63830(8) 0.27118(7) 0.0332(2) Uani d . 1 1
N N2 0.37353(16) 0.60790(9) 0.20808(8) 0.0357(2) Uani d . 1 1
N N3 0.20986(19) 0.61941(10) 0.43971(8) 0.0432(3) Uani d . 1 1
Cl Cl1 0.00409(5) 0.74223(3) 0.13336(2) 0.04662(13) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 N1 118.58(11)
C2 C1 Cl1 123.81(10)
N1 C1 Cl1 117.61(9)
C1 C2 C3 119.48(12)
C1 C2 H2 120.3
C3 C2 H2 120.3
N3 C3 C2 122.62(12)
N3 C3 C13 117.87(12)
C2 C3 C13 119.50(13)
N3 C4 C5 132.85(12)
N3 C4 N1 122.10(11)
C5 C4 N1 105.05(11)
C4 C5 C6 105.62(11)
C4 C5 H5 127.2
C6 C5 H5 127.2
N2 C6 C5 112.96(11)
N2 C6 C7 119.48(11)
C5 C6 C7 127.56(11)
C12 C7 C8 118.62(12)
C12 C7 C6 121.13(12)
C8 C7 C6 120.25(12)
C9 C8 C7 120.39(14)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 120.34(14)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 119.88(14)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.10(15)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C7 120.65(14)
C11 C12 H12 119.7
C7 C12 H12 119.7
C3 C13 H13A 109.5
C3 C13 H13B 109.5
H13A C13 H13B 109.5
C3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N2 N1 C1 127.17(10)
N2 N1 C4 112.96(10)
C1 N1 C4 119.86(11)
C6 N2 N1 103.41(10)
C3 N3 C4 117.35(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3533(18)
C1 N1 1.3610(16)
C1 Cl1 1.7055(13)
C2 C3 1.4197(19)
C2 H2 0.9300
C3 N3 1.3201(18)
C3 C13 1.504(2)
C4 N3 1.3519(17)
C4 C5 1.3818(18)
C4 N1 1.4019(16)
C5 C6 1.3966(18)
C5 H5 0.9300
C6 N2 1.3503(16)
C6 C7 1.4727(17)
C7 C12 1.3897(19)
C7 C8 1.3940(18)
C8 C9 1.386(2)
C8 H8 0.9300
C9 C10 1.379(2)
C9 H9 0.9300
C10 C11 1.377(2)
C10 H10 0.9300
C11 C12 1.389(2)
C11 H11 0.9300
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N1 N2 1.3532(15)
