#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/03/7220306.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_7220306
loop_
_publ_author_name
'Frizzo, Clarissa P.'
'Tier, Aniele Z.'
'Gindri, Izabelle M.'
'Meyer, Alexandre R.'
'Black, Gabrielle'
'Belladona, Andrei L.'
'Martins, Marcos A. P.'
_publ_section_title
;
 Thermodynamic, energetic, and topological properties of crystal packing
 of pyrazolo[1,5-a]pyrimidines governed by weak electrostatic
 intermolecular interactions
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              4325
_journal_paper_doi               10.1039/C5CE00613A
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C13 H10 F N3'
_chemical_formula_sum            'C13 H10 F N3'
_chemical_formula_weight         227.24
_chemical_melting_point          ?
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_name_systematic
;
2-methyl-7-(4-fluorophenyl)pyrazolo[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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2015-03-25T06:54:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.724(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8161(2)
_cell_length_b                   10.6532(5)
_cell_length_c                   25.8317(12)
_cell_measurement_reflns_used    1987
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.699
_cell_measurement_theta_min      2.478
_cell_volume                     1050.07(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-II'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8925
_diffrn_reflns_theta_full        26.72
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1124P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1941
_reflns_number_gt                1329
_reflns_number_total             2199
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ce00613a2.cif
_cod_data_source_block           p21ns
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7220304--7220315.cif.
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7220306
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_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
C3A C 0.3978(6) 0.2255(3) 0.19200(11) 0.0293(7) Uani 1 1 d .
C7 C 0.5387(6) 0.4390(2) 0.16745(10) 0.0266(6) Uani 1 1 d .
C72 C 0.4195(6) 0.6591(3) 0.14451(11) 0.0304(7) Uani 1 1 d .
H9 H 0.3423 0.6706 0.1782 0.037 Uiso 1 1 calc R
C71 C 0.5323(6) 0.5404(2) 0.12878(10) 0.0262(6) Uani 1 1 d .
C74 C 0.5408(7) 0.7393(3) 0.06159(11) 0.0326(7) Uani 1 1 d .
C73 C 0.4211(7) 0.7595(3) 0.11068(11) 0.0332(7) Uani 1 1 d .
H10 H 0.3434 0.8383 0.1209 0.04 Uiso 1 1 calc R
C2 C 0.1640(6) 0.1675(3) 0.11699(11) 0.0298(7) Uani 1 1 d .
C6 C 0.6612(6) 0.4533(3) 0.21698(11) 0.0320(7) Uani 1 1 d .
H6 H 0.7543 0.5299 0.2275 0.038 Uiso 1 1 calc R
C75 C 0.6569(6) 0.6242(3) 0.04466(11) 0.0320(7) Uani 1 1 d .
H12 H 0.7378 0.6142 0.0111 0.038 Uiso 1 1 calc R
C3 C 0.2408(6) 0.1259(3) 0.16660(11) 0.0315(7) Uani 1 1 d .
H3 H 0.1957 0.0466 0.1801 0.038 Uiso 1 1 calc R
C5 C 0.6476(6) 0.3525(3) 0.25219(11) 0.0342(7) Uani 1 1 d .
H5 H 0.7352 0.3657 0.2855 0.041 Uiso 1 1 calc R
C76 C 0.6509(6) 0.5244(3) 0.07820(10) 0.0297(7) Uani 1 1 d .
H13 H 0.7261 0.4459 0.0673 0.036 Uiso 1 1 calc R
C21 C -0.0040(7) 0.0959(3) 0.07365(11) 0.0359(7) Uani 1 1 d .
H1A H -0.0244 0.1489 0.0437 0.054 Uiso 1 1 calc R
H1B H -0.2328 0.0686 0.0838 0.054 Uiso 1 1 calc R
H1C H 0.1373 0.0241 0.0656 0.054 Uiso 1 1 calc R
N8 N 0.4098(5) 0.3221(2) 0.15523(8) 0.0261(6) Uani 1 1 d .
N4 N 0.5194(6) 0.2410(2) 0.24116(9) 0.0332(6) Uani 1 1 d .
N1 N 0.2650(5) 0.2875(2) 0.10905(8) 0.0285(6) Uani 1 1 d .
F1 F 0.5445(5) 0.83828(16) 0.02842(7) 0.0475(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3A 0.0275(12) 0.0308(16) 0.0297(16) 0.0055(13) 0.0046(11) 0.0051(11)
C7 0.0254(11) 0.0262(16) 0.0282(16) -0.0039(13) 0.0017(10) 0.0026(10)
C72 0.0295(12) 0.0336(17) 0.0281(16) -0.0020(13) 0.0010(11) -0.0007(11)
C71 0.0252(11) 0.0270(16) 0.0264(15) -0.0001(13) -0.0014(10) -0.0021(10)
C74 0.0362(14) 0.0298(17) 0.0317(17) 0.0088(13) -0.0051(12) -0.0048(11)
C73 0.0363(14) 0.0275(16) 0.0358(18) -0.0033(14) -0.0004(12) 0.0028(11)
C2 0.0259(11) 0.0280(17) 0.0355(17) -0.0011(13) 0.0044(11) 0.0024(10)
C6 0.0316(13) 0.0328(17) 0.0315(17) -0.0039(14) -0.0016(11) -0.0006(11)
C75 0.0328(13) 0.0385(19) 0.0249(16) -0.0029(14) 0.0019(11) -0.0051(11)
C3 0.0361(13) 0.0231(16) 0.0354(17) 0.0032(13) 0.0058(12) 0.0002(11)
C5 0.0350(13) 0.0380(19) 0.0294(17) 0.0002(14) -0.0015(12) 0.0047(12)
C76 0.0278(12) 0.0300(17) 0.0313(16) -0.0031(13) -0.0001(11) 0.0006(11)
C21 0.0330(12) 0.0353(17) 0.0393(18) -0.0048(14) 0.0005(11) -0.0028(12)
N8 0.0247(9) 0.0279(13) 0.0259(13) -0.0008(10) 0.0011(8) 0.0018(9)
N4 0.0360(12) 0.0355(15) 0.0280(14) 0.0018(11) 0.0020(10) 0.0045(10)
N1 0.0297(10) 0.0278(14) 0.0279(13) -0.0016(11) -0.0008(9) 0.0000(9)
F1 0.0676(12) 0.0373(12) 0.0375(11) 0.0106(9) -0.0017(8) -0.0030(8)
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 0 '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'
F F 0.0171 0.0103 '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
N4 C3A C3 132.8(3)
N4 C3A N8 122.1(2)
C3 C3A N8 105.1(2)
C6 C7 N8 115.7(3)
C6 C7 C71 123.9(2)
N8 C7 C71 120.4(2)
C73 C72 C71 120.8(3)
C72 C71 C76 119.1(2)
C72 C71 C7 118.0(2)
C76 C71 C7 122.8(2)
F1 C74 C73 117.9(3)
F1 C74 C75 119.0(3)
C73 C74 C75 123.1(3)
C74 C73 C72 117.9(3)
N1 C2 C3 112.7(3)
N1 C2 C21 119.3(3)
C3 C2 C21 127.9(3)
C7 C6 C5 120.4(3)
C76 C75 C74 118.8(3)
C3A C3 C2 106.2(2)
N4 C5 C6 124.4(3)
C75 C76 C71 120.3(3)
N1 N8 C7 126.0(2)
N1 N8 C3A 112.3(2)
C7 N8 C3A 121.6(2)
C5 N4 C3A 115.8(3)
C2 N1 N8 103.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3A N4 1.357(4)
C3A C3 1.381(4)
C3A N8 1.402(3)
C7 C6 1.365(4)
C7 N8 1.374(3)
C7 C71 1.471(4)
C72 C73 1.381(4)
C72 C71 1.398(4)
C71 C76 1.399(4)
C74 F1 1.359(3)
C74 C73 1.370(4)
C74 C75 1.377(4)
C2 N1 1.351(4)
C2 C3 1.384(4)
C2 C21 1.493(4)
C6 C5 1.409(4)
C75 C76 1.371(4)
C5 N4 1.314(4)
N8 N1 1.359(3)
