# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p212121
_database_code_depnum_ccdc_archive 'CCDC 734998'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T06:34:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'2-methyl-5-(4-bromophenyl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C14 H9 Br F3 N3'
_chemical_formula_sum            'C14 H9 Br F3 N3'
_chemical_formula_weight         356.15
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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'

_cell_length_a                   4.7574(7)
_cell_length_b                   11.0476(17)
_cell_length_c                   26.177(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1375.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2957
_cell_measurement_theta_min      3.219
_cell_measurement_theta_max      25.224

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.018
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_T_max  0.933

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_number            13211
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2
_diffrn_reflns_theta_max         27.36
_diffrn_reflns_theta_full        27.36
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3093
_reflns_number_gt                1889
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0454P)²+1.1686P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br Br 1.49902(15) 0.65009(5) 0.96774(2) 0.0594(2) Uani 1 1 d . . .
F1 F 0.5994(9) 0.2267(4) 0.71923(14) 0.0812(13) Uani 1 1 d . . .
F2 F 0.5286(14) 0.0378(4) 0.73367(15) 0.0939(14) Uani 1 1 d . . .
F3 F 0.1838(9) 0.1606(5) 0.73361(15) 0.0944(14) Uani 1 1 d . . .
N4 N 0.5691(9) 0.2007(4) 0.90806(18) 0.0450(12) Uani 1 1 d . . .
N8 N 0.3531(11) 0.1014(4) 0.83631(19) 0.0498(12) Uani 1 1 d . . .
C5 C 0.7064(12) 0.2689(5) 0.8754(2) 0.0438(13) Uani 1 1 d . . .
C3A C 0.3926(12) 0.1170(5) 0.8889(2) 0.0463(14) Uani 1 1 d . . .
C52 C 1.0241(16) 0.4493(5) 0.8669(2) 0.0538(14) Uani 1 1 d . . .
H52 H 0.9852 0.4516 0.8321 0.065 Uiso 1 1 calc R . .
C51 C 0.9039(10) 0.3596(5) 0.8971(2) 0.0430(13) Uani 1 1 d . . .
C55 C 1.1500(12) 0.4398(5) 0.9692(3) 0.0515(14) Uani 1 1 d . . .
H55 H 1.1944 0.4364 1.0038 0.062 Uiso 1 1 calc R . .
C7 C 0.4987(15) 0.1721(4) 0.80296(19) 0.0486(12) Uani 1 1 d . . .
C2 C 0.0903(12) -0.0289(5) 0.8712(3) 0.0558(17) Uani 1 1 d . . .
C3 C 0.2206(13) 0.0321(5) 0.9114(3) 0.0543(15) Uani 1 1 d . . .
H3 H 0.1962 0.0183 0.9461 0.065 Uiso 1 1 calc R . .
N1 N 0.1686(11) 0.0117(5) 0.8254(2) 0.0558(14) Uani 1 1 d . . .
C53 C 1.2001(13) 0.5347(6) 0.8880(2) 0.0553(16) Uani 1 1 d . . .
H53 H 1.2767 0.5955 0.8678 0.066 Uiso 1 1 calc R . .
C56 C 0.9729(14) 0.3556(5) 0.9482(2) 0.0488(13) Uani 1 1 d . . .
H56 H 0.8983 0.2948 0.9687 0.059 Uiso 1 1 calc R . .
C6 C 0.6713(13) 0.2571(5) 0.8216(2) 0.0508(15) Uani 1 1 d . . .
H6 H 0.7678 0.3083 0.7995 0.061 Uiso 1 1 calc R . .
C54 C 1.2611(12) 0.5291(5) 0.9391(2) 0.0451(14) Uani 1 1 d . . .
C21 C -0.1159(14) -0.1311(6) 0.8740(3) 0.073(2) Uani 1 1 d . . .
H1A H -0.1691 -0.1548 0.8401 0.11 Uiso 1 1 calc R . .
H1B H -0.2796 -0.1053 0.8925 0.11 Uiso 1 1 calc R . .
H1C H -0.0313 -0.1985 0.8912 0.11 Uiso 1 1 calc R . .
C71 C 0.4508(16) 0.1479(8) 0.7472(3) 0.066(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Br C54 1.905(6) . ?
F1 C71 1.339(8) . ?
F2 C71 1.320(8) . ?
F3 C71 1.327(8) . ?
N4 C5 1.314(7) . ?
N4 C3A 1.346(7) . ?
N8 N1 1.355(6) . ?
N8 C7 1.361(7) . ?
N8 C3A 1.400(8) . ?
C5 C6 1.423(8) . ?
C5 C51 1.487(8) . ?
C3A C3 1.376(8) . ?
C52 C53 1.377(9) . ?
C52 C51 1.390(7) . ?
C52 H52 0.93 . ?
C51 C56 1.379(7) . ?
C55 C54 1.369(8) . ?
C55 C56 1.371(8) . ?
C55 H55 0.93 . ?
C7 C6 1.340(8) . ?
C7 C71 1.501(8) . ?
C2 N1 1.333(8) . ?
C2 C3 1.395(8) . ?
C2 C21 1.497(8) . ?
C3 H3 0.93 . ?
C53 C54 1.369(8) . ?
C53 H53 0.93 . ?
C56 H56 0.93 . ?
C6 H6 0.93 . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?

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
C5 N4 C3A 117.5(5) . . ?
N1 N8 C7 127.9(5) . . ?
N1 N8 C3A 112.6(5) . . ?
C7 N8 C3A 119.5(5) . . ?
N4 C5 C6 122.2(5) . . ?
N4 C5 C51 116.8(5) . . ?
C6 C5 C51 120.9(5) . . ?
N4 C3A C3 132.8(6) . . ?
N4 C3A N8 122.3(5) . . ?
C3 C3A N8 104.9(5) . . ?
C53 C52 C51 120.7(5) . . ?
C53 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
C56 C51 C52 118.4(5) . . ?
C56 C51 C5 120.0(5) . . ?
C52 C51 C5 121.5(5) . . ?
C54 C55 C56 119.7(6) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C6 C7 N8 118.7(5) . . ?
C6 C7 C71 124.9(6) . . ?
N8 C7 C71 116.4(6) . . ?
N1 C2 C3 113.1(5) . . ?
N1 C2 C21 118.7(6) . . ?
C3 C2 C21 128.2(6) . . ?
C3A C3 C2 105.7(6) . . ?
C3A C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
C2 N1 N8 103.7(5) . . ?
C54 C53 C52 119.3(6) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C55 C56 C51 120.9(6) . . ?
C55 C56 H56 119.5 . . ?
C51 C56 H56 119.5 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C53 C54 C55 120.9(6) . . ?
C53 C54 Br 118.6(5) . . ?
C55 C54 Br 120.5(5) . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.5 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?
F2 C71 F3 107.1(7) . . ?
F2 C71 F1 107.7(6) . . ?
F3 C71 F1 106.9(6) . . ?
F2 C71 C7 112.5(6) . . ?
F3 C71 C7 112.8(6) . . ?
F1 C71 C7 109.6(6) . . ?

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
C3A N4 C5 C6 0.5(8) . . . . ?
C3A N4 C5 C51 -179.1(5) . . . . ?
C5 N4 C3A C3 179.8(6) . . . . ?
C5 N4 C3A N8 0.0(8) . . . . ?
N1 N8 C3A N4 179.4(5) . . . . ?
C7 N8 C3A N4 0.6(8) . . . . ?
N1 N8 C3A C3 -0.4(6) . . . . ?
C7 N8 C3A C3 -179.2(5) . . . . ?
C53 C52 C51 C56 -2.3(9) . . . . ?
C53 C52 C51 C5 178.1(5) . . . . ?
N4 C5 C51 C56 11.1(8) . . . . ?
C6 C5 C51 C56 -168.5(6) . . . . ?
N4 C5 C51 C52 -169.2(5) . . . . ?
C6 C5 C51 C52 11.2(8) . . . . ?
N1 N8 C7 C6 179.6(5) . . . . ?
C3A N8 C7 C6 -1.7(8) . . . . ?
N1 N8 C7 C71 -0.2(9) . . . . ?
C3A N8 C7 C71 178.5(6) . . . . ?
N4 C3A C3 C2 -179.6(6) . . . . ?
N8 C3A C3 C2 0.2(6) . . . . ?
N1 C2 C3 C3A 0.0(7) . . . . ?
C21 C2 C3 C3A 179.4(6) . . . . ?
C3 C2 N1 N8 -0.2(7) . . . . ?
C21 C2 N1 N8 -179.7(5) . . . . ?
C7 N8 N1 C2 179.1(6) . . . . ?
C3A N8 N1 C2 0.4(6) . . . . ?
C51 C52 C53 C54 1.4(9) . . . . ?
C54 C55 C56 C51 -0.3(9) . . . . ?
C52 C51 C56 C55 1.7(9) . . . . ?
C5 C51 C56 C55 -178.6(5) . . . . ?
N8 C7 C6 C5 2.2(8) . . . . ?
C71 C7 C6 C5 -178.0(6) . . . . ?
N4 C5 C6 C7 -1.7(9) . . . . ?
C51 C5 C6 C7 177.9(5) . . . . ?
C52 C53 C54 C55 0.1(9) . . . . ?
C52 C53 C54 Br -178.8(5) . . . . ?
C56 C55 C54 C53 -0.7(9) . . . . ?
C56 C55 C54 Br 178.2(4) . . . . ?
C6 C7 C71 F2 117.8(7) . . . . ?
N8 C7 C71 F2 -62.4(8) . . . . ?
C6 C7 C71 F3 -121.0(8) . . . . ?
N8 C7 C71 F3 58.9(9) . . . . ?
C6 C7 C71 F1 -2.0(9) . . . . ?
N8 C7 C71 F1 177.8(5) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 734999'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T06:48:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2-methyl-7-phenylpyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C13 H11 N3'
_chemical_formula_sum            'C13 H11 N3'
_chemical_formula_weight         209.25
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
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'

_cell_length_a                   3.9185(3)
_cell_length_b                   10.5324(10)
_cell_length_c                   25.539(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.642(3)
_cell_angle_gamma                90
_cell_volume                     1053.97(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1022
_cell_measurement_theta_min      2.507
_cell_measurement_theta_max      19.92

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9927

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_number            9242
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_full        27.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             2310
_reflns_number_gt                1387
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0820P)²+0.0717P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.025(5)
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.163
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'

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
C7 C 1.0361(4) 0.44070(19) 0.16420(7) 0.0411(5) Uani 1 1 d . . .
C3A C 0.8859(5) 0.2256(2) 0.18792(8) 0.0457(5) Uani 1 1 d . . .
C6 C 1.1554(5) 0.4532(2) 0.21444(8) 0.0508(6) Uani 1 1 d . . .
H6 H 1.2497 0.5297 0.2255 0.061 Uiso 1 1 calc R . .
C71 C 1.0379(5) 0.54605(19) 0.12580(7) 0.0409(5) Uani 1 1 d . . .
C76 C 1.1563(5) 0.5305(2) 0.07475(8) 0.0472(5) Uani 1 1 d . . .
H13 H 1.228 0.4511 0.0633 0.057 Uiso 1 1 calc R . .
C2 C 0.6603(5) 0.1705(2) 0.11167(8) 0.0465(5) Uani 1 1 d . . .
C5 C 1.1354(5) 0.3501(2) 0.24938(8) 0.0551(6) Uani 1 1 d . . .
H5 H 1.2214 0.3616 0.2831 0.066 Uiso 1 1 calc R . .
C74 C 1.0545(6) 0.7513(2) 0.05792(9) 0.0583(6) Uani 1 1 d . . .
H11 H 1.0585 0.82 0.0351 0.07 Uiso 1 1 calc R . .
C73 C 0.9374(6) 0.7669(2) 0.10819(9) 0.0576(6) Uani 1 1 d . . .
H10 H 0.864 0.8463 0.1193 0.069 Uiso 1 1 calc R . .
C3 C 0.7275(5) 0.1270(2) 0.16186(8) 0.0534(6) Uani 1 1 d . . .
H3 H 0.6761 0.0472 0.1753 0.064 Uiso 1 1 calc R . .
C72 C 0.9288(5) 0.6648(2) 0.14199(8) 0.0497(6) Uani 1 1 d . . .
H9 H 0.8494 0.6758 0.1759 0.06 Uiso 1 1 calc R . .
C75 C 1.1657(6) 0.6338(2) 0.04152(8) 0.0548(6) Uani 1 1 d . . .
H12 H 1.2479 0.624 0.0077 0.066 Uiso 1 1 calc R . .
C21 C 0.4950(6) 0.1009(2) 0.06701(9) 0.0608(7) Uani 1 1 d . . .
H1A H 0.4818 0.1556 0.037 0.091 Uiso 1 1 calc R . .
H1B H 0.2693 0.0752 0.0767 0.091 Uiso 1 1 calc R . .
H1C H 0.628 0.0272 0.0587 0.091 Uiso 1 1 calc R . .
N8 N 0.9062(4) 0.32417(16) 0.15122(6) 0.0398(4) Uani 1 1 d . . .
N1 N 0.7662(4) 0.29089(16) 0.10399(6) 0.0453(5) Uani 1 1 d . . .
N4 N 1.0041(5) 0.23907(19) 0.23769(7) 0.0553(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
C7 C6 1.367(3) . ?
C7 N8 1.368(2) . ?
C7 C71 1.481(3) . ?
C3A N4 1.355(3) . ?
C3A C3 1.378(3) . ?
C3A N8 1.401(2) . ?
C6 C5 1.408(3) . ?
C6 H6 0.93 . ?
C71 C72 1.387(3) . ?
C71 C76 1.399(3) . ?
C76 C75 1.381(3) . ?
C76 H13 0.93 . ?
C2 N1 1.349(3) . ?
C2 C3 1.384(3) . ?
C2 C21 1.497(3) . ?
C5 N4 1.310(3) . ?
C5 H5 0.93 . ?
C74 C73 1.378(3) . ?
C74 C75 1.379(3) . ?
C74 H11 0.93 . ?
C73 C72 1.379(3) . ?
C73 H10 0.93 . ?
C3 H3 0.93 . ?
C72 H9 0.93 . ?
C75 H12 0.93 . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?
N8 N1 1.365(2) . ?

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
C6 C7 N8 115.85(19) . . ?
C6 C7 C71 123.06(19) . . ?
N8 C7 C71 121.07(17) . . ?
N4 C3A C3 132.8(2) . . ?
N4 C3A N8 121.92(19) . . ?
C3 C3A N8 105.30(18) . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120 . . ?
C5 C6 H6 120 . . ?
C72 C71 C76 119.37(19) . . ?
C72 C71 C7 118.35(18) . . ?
C76 C71 C7 122.24(18) . . ?
C75 C76 C71 119.5(2) . . ?
C75 C76 H13 120.3 . . ?
C71 C76 H13 120.3 . . ?
N1 C2 C3 112.99(19) . . ?
N1 C2 C21 118.7(2) . . ?
C3 C2 C21 128.3(2) . . ?
N4 C5 C6 124.6(2) . . ?
N4 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C73 C74 C75 120.0(2) . . ?
C73 C74 H11 120 . . ?
C75 C74 H11 120 . . ?
C74 C73 C72 120.0(2) . . ?
C74 C73 H10 120 . . ?
C72 C73 H10 120 . . ?
C3A C3 C2 106.10(19) . . ?
C3A C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
C73 C72 C71 120.5(2) . . ?
C73 C72 H9 119.8 . . ?
C71 C72 H9 119.8 . . ?
C74 C75 C76 120.7(2) . . ?
C74 C75 H12 119.7 . . ?
C76 C75 H12 119.7 . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.5 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?
N1 N8 C7 126.10(16) . . ?
N1 N8 C3A 112.06(16) . . ?
C7 N8 C3A 121.74(17) . . ?
C2 N1 N8 103.53(16) . . ?
C5 N4 C3A 115.84(19) . . ?

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
N8 C7 C6 C5 -0.9(3) . . . . ?
C71 C7 C6 C5 177.88(18) . . . . ?
C6 C7 C71 C72 -44.9(3) . . . . ?
N8 C7 C71 C72 133.8(2) . . . . ?
C6 C7 C71 C76 132.8(2) . . . . ?
N8 C7 C71 C76 -48.5(3) . . . . ?
C72 C71 C76 C75 0.6(3) . . . . ?
C7 C71 C76 C75 -177.08(18) . . . . ?
C7 C6 C5 N4 -0.7(3) . . . . ?
C75 C74 C73 C72 -0.5(3) . . . . ?
N4 C3A C3 C2 178.8(2) . . . . ?
N8 C3A C3 C2 -0.2(2) . . . . ?
N1 C2 C3 C3A 0.1(2) . . . . ?
C21 C2 C3 C3A 179.2(2) . . . . ?
C74 C73 C72 C71 0.1(3) . . . . ?
C76 C71 C72 C73 -0.1(3) . . . . ?
C7 C71 C72 C73 177.68(18) . . . . ?
C73 C74 C75 C76 1.0(3) . . . . ?
C71 C76 C75 C74 -1.1(3) . . . . ?
C6 C7 N8 N1 178.33(16) . . . . ?
C71 C7 N8 N1 -0.4(3) . . . . ?
C6 C7 N8 C3A 2.3(3) . . . . ?
C71 C7 N8 C3A -176.51(16) . . . . ?
N4 C3A N8 N1 -178.80(17) . . . . ?
C3 C3A N8 N1 0.3(2) . . . . ?
N4 C3A N8 C7 -2.2(3) . . . . ?
C3 C3A N8 C7 176.89(16) . . . . ?
C3 C2 N1 N8 0.1(2) . . . . ?
C21 C2 N1 N8 -179.06(17) . . . . ?
C7 N8 N1 C2 -176.66(17) . . . . ?
C3A N8 N1 C2 -0.27(19) . . . . ?
C6 C5 N4 C3A 0.9(3) . . . . ?
C3 C3A N4 C5 -178.3(2) . . . . ?
N8 C3A N4 C5 0.6(3) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21ns
_database_code_depnum_ccdc_archive 'CCDC 735000'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T06:54:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2-methyl-7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C13 H10 F N3'
_chemical_formula_sum            'C13 H10 F N3'
_chemical_formula_weight         227.24
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
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'

_cell_length_a                   3.8161(2)
_cell_length_b                   10.6532(5)
_cell_length_c                   25.8317(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.724(3)
_cell_angle_gamma                90
_cell_volume                     1050.07(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1987
_cell_measurement_theta_min      2.478
_cell_measurement_theta_max      26.699

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.9909

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_number            8925
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_full        26.72
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             2199
_reflns_number_gt                1329
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1124P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.025(7)
_refine_ls_number_reflns         2199
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.101

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
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 . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
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) . ?

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
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) . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21
_database_code_depnum_ccdc_archive 'CCDC 735001'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T07:04:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2-methyl-7-(4-bromophenyl)-pyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C13 H10 Br N3'
_chemical_formula_sum            'C13 H10 Br N3'
_chemical_formula_weight         288.15
_chemical_melting_point          none
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  P2yb
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.91340(10)
_cell_length_b                   10.8096(2)
_cell_length_c                   13.8568(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.9070(10)
_cell_angle_gamma                90
_cell_volume                     581.92(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1475
_cell_measurement_theta_min      2.396
_cell_measurement_theta_max      21.667

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.074
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.511
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.48773
_exptl_absorpt_correction_T_max  0.86209

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_number            6214
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             3182
_reflns_number_gt                2197
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3182
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br Br 0.14676(12) 0.02244(4) 0.02825(4) 0.05966(19) Uani 1 1 d . . .
N8 N 0.1108(7) 0.5299(4) 0.3315(2) 0.0345(7) Uani 1 1 d . . .
C76 C 0.3142(11) 0.3499(4) 0.1782(3) 0.0401(10) Uani 1 1 d . . .
H13 H 0.3872 0.4292 0.1645 0.048 Uiso 1 1 calc R . .
C74 C 0.1839(11) 0.1427(4) 0.1278(3) 0.0410(10) Uani 1 1 d . . .
C71 C 0.2239(10) 0.3226(4) 0.2703(3) 0.0340(9) Uani 1 1 d . . .
N4 N 0.2827(11) 0.6003(4) 0.4947(3) 0.0468(10) Uani 1 1 d . . .
C5 C 0.4187(13) 0.4907(4) 0.5102(4) 0.0455(12) Uani 1 1 d . . .
H5 H 0.5304 0.4742 0.5719 0.055 Uiso 1 1 calc R . .
C72 C 0.1187(12) 0.2028(4) 0.2896(4) 0.0416(10) Uani 1 1 d . . .
H9 H 0.0645 0.183 0.3512 0.05 Uiso 1 1 calc R . .
C6 C 0.4090(12) 0.3963(4) 0.4410(3) 0.0425(10) Uani 1 1 d . . .
H6 H 0.5103 0.3202 0.4575 0.051 Uiso 1 1 calc R . .
C75 C 0.2954(12) 0.2597(4) 0.1080(3) 0.0421(10) Uani 1 1 d . . .
H12 H 0.3581 0.2777 0.0469 0.05 Uiso 1 1 calc R . .
C3 C -0.0524(12) 0.7219(4) 0.3601(4) 0.0457(11) Uani 1 1 d . . .
H3 H -0.0904 0.7979 0.3884 0.055 Uiso 1 1 calc R . .
C3A C 0.1243(10) 0.6215(4) 0.4044(3) 0.0385(10) Uani 1 1 d . . .
C7 C 0.2503(11) 0.4163(4) 0.3490(3) 0.0359(9) Uani 1 1 d . . .
C73 C 0.0945(12) 0.1145(4) 0.2189(4) 0.0451(11) Uani 1 1 d . . .
H10 H 0.018 0.0354 0.2318 0.054 Uiso 1 1 calc R . .
N1 N -0.0668(9) 0.5696(3) 0.2461(3) 0.0376(8) Uani 1 1 d . . .
C2 C -0.1604(11) 0.6861(4) 0.2655(3) 0.0382(10) Uani 1 1 d . . .
C21 C -0.3611(13) 0.7595(5) 0.1865(4) 0.0536(13) Uani 1 1 d . . .
H1A H -0.3977 0.7105 0.1284 0.08 Uiso 1 1 calc R . .
H1B H -0.235 0.8328 0.1741 0.08 Uiso 1 1 calc R . .
H1C H -0.5793 0.7823 0.2063 0.08 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Br C74 1.889(4) . ?
N8 C7 1.354(6) . ?
N8 N1 1.367(5) . ?
N8 C3A 1.412(6) . ?
C76 C75 1.373(6) . ?
C76 C71 1.396(6) . ?
C76 H13 0.93 . ?
C74 C75 1.376(6) . ?
C74 C73 1.383(7) . ?
C71 C72 1.394(6) . ?
C71 C7 1.482(6) . ?
N4 C5 1.306(6) . ?
N4 C3A 1.348(6) . ?
C5 C6 1.397(7) . ?
C5 H5 0.93 . ?
C72 C73 1.363(7) . ?
C72 H9 0.93 . ?
C6 C7 1.367(6) . ?
C6 H6 0.93 . ?
C75 H12 0.93 . ?
C3 C2 1.383(7) . ?
C3 C3A 1.389(7) . ?
C3 H3 0.93 . ?
C73 H10 0.93 . ?
N1 C2 1.347(6) . ?
C2 C21 1.496(7) . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?

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
C7 N8 N1 126.3(4) . . ?
C7 N8 C3A 121.9(3) . . ?
N1 N8 C3A 111.7(4) . . ?
C75 C76 C71 120.0(4) . . ?
C75 C76 H13 120 . . ?
C71 C76 H13 120 . . ?
C75 C74 C73 120.4(4) . . ?
C75 C74 Br 119.0(4) . . ?
C73 C74 Br 120.6(3) . . ?
C72 C71 C76 119.0(4) . . ?
C72 C71 C7 119.3(4) . . ?
C76 C71 C7 121.7(4) . . ?
C5 N4 C3A 116.1(4) . . ?
N4 C5 C6 125.0(5) . . ?
N4 C5 H5 117.5 . . ?
C6 C5 H5 117.5 . . ?
C73 C72 C71 120.6(4) . . ?
C73 C72 H9 119.7 . . ?
C71 C72 H9 119.7 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C76 C75 C74 120.2(4) . . ?
C76 C75 H12 119.9 . . ?
C74 C75 H12 119.9 . . ?
C2 C3 C3A 106.2(4) . . ?
C2 C3 H3 126.9 . . ?
C3A C3 H3 126.9 . . ?
N4 C3A C3 133.8(4) . . ?
N4 C3A N8 121.2(4) . . ?
C3 C3A N8 105.0(4) . . ?
N8 C7 C6 116.0(4) . . ?
N8 C7 C71 119.8(4) . . ?
C6 C7 C71 124.2(4) . . ?
C72 C73 C74 119.9(4) . . ?
C72 C73 H10 120.1 . . ?
C74 C73 H10 120.1 . . ?
C2 N1 N8 104.0(4) . . ?
N1 C2 C3 113.0(4) . . ?
N1 C2 C21 118.7(4) . . ?
C3 C2 C21 128.2(4) . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.5 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?

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
C75 C76 C71 C72 0.7(7) . . . . ?
C75 C76 C71 C7 178.2(4) . . . . ?
C3A N4 C5 C6 -0.3(8) . . . . ?
C76 C71 C72 C73 -1.9(7) . . . . ?
C7 C71 C72 C73 -179.5(4) . . . . ?
N4 C5 C6 C7 0.5(8) . . . . ?
C71 C76 C75 C74 0.7(7) . . . . ?
C73 C74 C75 C76 -0.9(7) . . . . ?
Br C74 C75 C76 177.9(3) . . . . ?
C5 N4 C3A C3 178.7(5) . . . . ?
C5 N4 C3A N8 -0.5(6) . . . . ?
C2 C3 C3A N4 -179.1(5) . . . . ?
C2 C3 C3A N8 0.1(5) . . . . ?
C7 N8 C3A N4 1.1(6) . . . . ?
N1 N8 C3A N4 178.9(4) . . . . ?
C7 N8 C3A C3 -178.2(4) . . . . ?
N1 N8 C3A C3 -0.5(4) . . . . ?
N1 N8 C7 C6 -178.3(4) . . . . ?
C3A N8 C7 C6 -0.9(6) . . . . ?
N1 N8 C7 C71 1.6(6) . . . . ?
C3A N8 C7 C71 179.0(3) . . . . ?
C5 C6 C7 N8 0.1(6) . . . . ?
C5 C6 C7 C71 -179.7(4) . . . . ?
C72 C71 C7 N8 -132.5(4) . . . . ?
C76 C71 C7 N8 49.9(6) . . . . ?
C72 C71 C7 C6 47.3(6) . . . . ?
C76 C71 C7 C6 -130.2(5) . . . . ?
C71 C72 C73 C74 1.8(7) . . . . ?
C75 C74 C73 C72 -0.4(7) . . . . ?
Br C74 C73 C72 -179.2(3) . . . . ?
C7 N8 N1 C2 178.2(4) . . . . ?
C3A N8 N1 C2 0.6(4) . . . . ?
N8 N1 C2 C3 -0.5(5) . . . . ?
N8 N1 C2 C21 179.6(4) . . . . ?
C3A C3 C2 N1 0.3(5) . . . . ?
C3A C3 C2 C21 -179.8(4) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p212121
_database_code_depnum_ccdc_archive 'CCDC 735002'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T07:11:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2-methyl-7-(pyrid-2-yl)pyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C12 H10 N4'
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24
_chemical_melting_point          none
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.0774(3)
_cell_length_b                   12.7591(6)
_cell_length_c                   19.5223(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1015.63(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1128
_cell_measurement_theta_min      2.627
_cell_measurement_theta_max      19.23

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'yellow pale'
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9436
_exptl_absorpt_correction_T_max  0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_number            11517
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_full        29.53
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             2819
_reflns_number_gt                1463
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0740P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2819
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'

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
N1 N 0.6999(4) 0.06150(15) 0.11796(8) 0.0518(5) Uani 1 1 d . . .
N8 N 0.5458(4) -0.03299(14) 0.11166(8) 0.0486(5) Uani 1 1 d . . .
C74 C 0.1625(7) 0.1004(2) -0.12255(13) 0.0695(7) Uani 1 1 d . . .
H10 H 0.1103 0.1334 -0.1636 0.083 Uiso 1 1 calc R . .
N4 N 0.4734(5) -0.19333(17) 0.17477(11) 0.0674(6) Uani 1 1 d . . .
N72 N 0.2159(6) -0.05853(18) -0.05949(10) 0.0743(6) Uani 1 1 d . . .
C71 C 0.3077(5) -0.00291(17) -0.00526(11) 0.0495(5) Uani 1 1 d . . .
C7 C 0.3674(5) -0.06855(17) 0.05698(10) 0.0488(5) Uani 1 1 d . . .
C76 C 0.3295(7) 0.10367(19) -0.00653(12) 0.0642(6) Uani 1 1 d . . .
H12 H 0.3914 0.1405 0.0325 0.077 Uiso 1 1 calc R . .
C3A C 0.5996(5) -0.09604(19) 0.16946(12) 0.0555(6) Uani 1 1 d . . .
C6 C 0.2433(6) -0.16644(18) 0.06346(11) 0.0577(6) Uani 1 1 d . . .
H6 H 0.1182 -0.1946 0.0281 0.069 Uiso 1 1 calc R . .
C2 C 0.8450(5) 0.0578(2) 0.18017(11) 0.0562(6) Uani 1 1 d . . .
C5 C 0.2998(6) -0.2258(2) 0.12223(13) 0.0663(7) Uani 1 1 d . . .
H5 H 0.2089 -0.2925 0.1244 0.08 Uiso 1 1 calc R . .
C3 C 0.7908(5) -0.0370(2) 0.21252(11) 0.0620(6) Uani 1 1 d . . .
H3 H 0.869 -0.057 0.2553 0.074 Uiso 1 1 calc R . .
C75 C 0.2575(7) 0.1568(2) -0.06724(12) 0.0701(7) Uani 1 1 d . . .
H11 H 0.2744 0.2294 -0.0696 0.084 Uiso 1 1 calc R . .
C73 C 0.1453(8) -0.0051(3) -0.11661(14) 0.0826(9) Uani 1 1 d . . .
H9 H 0.0798 -0.0431 -0.1549 0.099 Uiso 1 1 calc R . .
C21 C 1.0260(7) 0.1509(2) 0.20566(13) 0.0714(7) Uani 1 1 d . . .
H1A H 1.0212 0.205 0.1715 0.107 Uiso 1 1 calc R . .
H1B H 1.2494 0.1318 0.215 0.107 Uiso 1 1 calc R . .
H1C H 0.9246 0.1759 0.2469 0.107 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
N1 C2 1.352(3) . ?
N1 N8 1.365(2) . ?
N8 C7 1.369(3) . ?
N8 C3A 1.403(3) . ?
C74 C73 1.353(4) . ?
C74 C75 1.355(3) . ?
C74 H10 0.93 . ?
N4 C5 1.313(3) . ?
N4 C3A 1.348(3) . ?
N72 C71 1.329(3) . ?
N72 C73 1.338(3) . ?
C71 C76 1.363(3) . ?
C71 C7 1.496(3) . ?
C7 C6 1.354(3) . ?
C76 C75 1.397(3) . ?
C76 H12 0.93 . ?
C3A C3 1.372(3) . ?
C6 C5 1.394(3) . ?
C6 H6 0.93 . ?
C2 C3 1.382(3) . ?
C2 C21 1.484(3) . ?
C5 H5 0.93 . ?
C3 H3 0.93 . ?
C75 H11 0.93 . ?
C73 H9 0.93 . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?

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 N1 N8 104.55(18) . . ?
N1 N8 C7 127.40(17) . . ?
N1 N8 C3A 111.23(17) . . ?
C7 N8 C3A 121.3(2) . . ?
C73 C74 C75 118.4(2) . . ?
C73 C74 H10 120.8 . . ?
C75 C74 H10 120.8 . . ?
C5 N4 C3A 115.9(2) . . ?
C71 N72 C73 116.9(2) . . ?
N72 C71 C76 122.5(2) . . ?
N72 C71 C7 113.2(2) . . ?
C76 C71 C7 124.3(2) . . ?
C6 C7 N8 115.57(19) . . ?
C6 C7 C71 122.13(19) . . ?
N8 C7 C71 122.29(19) . . ?
C71 C76 C75 119.1(2) . . ?
C71 C76 H12 120.5 . . ?
C75 C76 H12 120.5 . . ?
N4 C3A C3 132.5(2) . . ?
N4 C3A N8 122.0(2) . . ?
C3 C3A N8 105.5(2) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C2 C3 111.8(2) . . ?
N1 C2 C21 119.4(2) . . ?
C3 C2 C21 128.8(2) . . ?
N4 C5 C6 124.1(2) . . ?
N4 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
C3A C3 C2 106.9(2) . . ?
C3A C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
C74 C75 C76 118.6(3) . . ?
C74 C75 H11 120.7 . . ?
C76 C75 H11 120.7 . . ?
N72 C73 C74 124.6(3) . . ?
N72 C73 H9 117.7 . . ?
C74 C73 H9 117.7 . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.5 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?

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
C2 N1 N8 C7 -178.89(18) . . . . ?
C2 N1 N8 C3A -1.0(2) . . . . ?
C73 N72 C71 C76 0.2(4) . . . . ?
C73 N72 C71 C7 177.5(2) . . . . ?
N1 N8 C7 C6 179.12(19) . . . . ?
C3A N8 C7 C6 1.4(3) . . . . ?
N1 N8 C7 C71 -2.1(3) . . . . ?
C3A N8 C7 C71 -179.81(17) . . . . ?
N72 C71 C7 C6 -19.6(3) . . . . ?
C76 C71 C7 C6 157.6(2) . . . . ?
N72 C71 C7 N8 161.7(2) . . . . ?
C76 C71 C7 N8 -21.1(3) . . . . ?
N72 C71 C76 C75 -1.0(4) . . . . ?
C7 C71 C76 C75 -177.9(2) . . . . ?
C5 N4 C3A C3 -179.5(2) . . . . ?
C5 N4 C3A N8 0.7(3) . . . . ?
N1 N8 C3A N4 -179.56(19) . . . . ?
C7 N8 C3A N4 -1.5(3) . . . . ?
N1 N8 C3A C3 0.6(2) . . . . ?
C7 N8 C3A C3 178.64(18) . . . . ?
N8 C7 C6 C5 -0.6(3) . . . . ?
C71 C7 C6 C5 -179.4(2) . . . . ?
N8 N1 C2 C3 1.0(2) . . . . ?
N8 N1 C2 C21 -177.40(18) . . . . ?
C3A N4 C5 C6 0.2(3) . . . . ?
C7 C6 C5 N4 -0.2(4) . . . . ?
N4 C3A C3 C2 -179.8(2) . . . . ?
N8 C3A C3 C2 0.1(2) . . . . ?
N1 C2 C3 C3A -0.7(2) . . . . ?
C21 C2 C3 C3A 177.5(2) . . . . ?
C73 C74 C75 C76 -0.7(4) . . . . ?
C71 C76 C75 C74 1.2(4) . . . . ?
C71 N72 C73 C74 0.2(5) . . . . ?
C75 C74 C73 N72 0.0(5) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 914143'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2012-10-04T09:37:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            2-methyl-5-(naphthalen-2-yl)-7-(trifluorometh
_chemical_formula_moiety         'C18 H12 F3 N3'
_chemical_formula_sum            'C18 H12 F3 N3'
_chemical_formula_weight         327.31
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2ybn
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'

_cell_length_a                   7.8462(5)
_cell_length_b                   11.2089(9)
_cell_length_c                   16.8641(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.389(5)
_cell_angle_gamma                90
_cell_volume                     1481.86(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1616
_cell_measurement_theta_min      2.182
_cell_measurement_theta_max      20.1095

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      nome
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_T_max  0.9908

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_number            23457
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             4299
_reflns_number_gt                1564
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4299
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.191
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
F73 F 0.6185(2) 0.06838(14) 1.05825(10) 0.0971(6) Uani 1 1 d . . .
F72 F 0.8773(2) 0.07872(13) 1.09916(9) 0.0868(5) Uani 1 1 d . . .
F71 F 0.8129(2) 0.09960(14) 0.97671(10) 0.0995(6) Uani 1 1 d . . .
N4 N 0.6944(2) 0.50132(17) 1.08254(12) 0.0527(5) Uani 1 1 d . . .
N1 N 0.6629(2) 0.23466(18) 1.19563(11) 0.0557(5) Uani 1 1 d . . .
N8 N 0.6941(2) 0.29956(17) 1.12975(11) 0.0490(5) Uani 1 1 d . . .
C55 C 0.9177(3) 0.7747(3) 0.70289(17) 0.0685(8) Uani 1 1 d . . .
H55 H 0.9347 0.8313 0.6637 0.082 Uiso 1 1 calc R . .
C56 C 0.9647(3) 0.6562(3) 0.69105(16) 0.0685(7) Uani 1 1 d . . .
H56 H 1.0109 0.634 0.6434 0.082 Uiso 1 1 calc R . .
C57 C 0.9438(3) 0.5731(2) 0.74831(15) 0.0628(7) Uani 1 1 d . . .
H57 H 0.978 0.4949 0.7398 0.075 Uiso 1 1 calc R . .
C57A C 0.8706(2) 0.6040(2) 0.82064(14) 0.0500(6) Uani 1 1 d . . .
C58 C 0.8457(2) 0.5212(2) 0.88129(14) 0.0525(6) Uani 1 1 d . . .
H58 H 0.8808 0.4428 0.8739 0.063 Uiso 1 1 calc R . .
C51 C 0.7723(2) 0.5499(2) 0.95099(14) 0.0480(6) Uani 1 1 d . . .
C5 C 0.7452(2) 0.4613(2) 1.01367(14) 0.0486(6) Uani 1 1 d . . .
C3A C 0.6696(2) 0.4219(2) 1.14101(14) 0.0493(6) Uani 1 1 d . . .
C3 C 0.6224(3) 0.4328(2) 1.21804(14) 0.0572(6) Uani 1 1 d . . .
H3 H 0.5968 0.503 1.2444 0.069 Uiso 1 1 calc R . .
C2 C 0.6205(3) 0.3182(2) 1.24871(14) 0.0543(6) Uani 1 1 d . . .
C21 C 0.5795(3) 0.2801(2) 1.33020(14) 0.0722(8) Uani 1 1 d . . .
H1A H 0.5889 0.195 1.3343 0.108 Uiso 1 1 calc R . .
H1B H 0.4652 0.304 1.3409 0.108 Uiso 1 1 calc R . .
H1C H 0.6579 0.3169 1.368 0.108 Uiso 1 1 calc R . .
C7 C 0.7435(3) 0.2579(2) 1.05877(14) 0.0490(6) Uani 1 1 d . . .
C6 C 0.7701(3) 0.3369(2) 1.00094(14) 0.0532(6) Uani 1 1 d . . .
H6 H 0.8052 0.3103 0.952 0.064 Uiso 1 1 calc R . .
C54 C 0.8471(3) 0.8069(2) 0.77159(16) 0.0633(7) Uani 1 1 d . . .
H54 H 0.8157 0.886 0.7789 0.076 Uiso 1 1 calc R . .
C53A C 0.8203(2) 0.7234(2) 0.83224(15) 0.0529(6) Uani 1 1 d . . .
C53 C 0.7459(3) 0.7527(2) 0.90461(15) 0.0626(7) Uani 1 1 d . . .
H53 H 0.7122 0.831 0.9134 0.075 Uiso 1 1 calc R . .
C52 C 0.7222(3) 0.6697(2) 0.96170(15) 0.0566(6) Uani 1 1 d . . .
H52 H 0.6724 0.692 1.0085 0.068 Uiso 1 1 calc R . .
C71 C 0.7630(3) 0.1258(2) 1.04880(16) 0.0632(7) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
F73 C71 1.320(3) . ?
F72 C71 1.320(3) . ?
F71 C71 1.326(3) . ?
N4 C5 1.322(3) . ?
N4 C3A 1.349(3) . ?
N1 C2 1.347(3) . ?
N1 N8 1.359(2) . ?
N8 C7 1.357(3) . ?
N8 C3A 1.398(3) . ?
C55 C54 1.354(3) . ?
C55 C56 1.394(4) . ?
C55 H55 0.93 . ?
C56 C57 1.357(3) . ?
C56 H56 0.93 . ?
C57 C57A 1.413(3) . ?
C57 H57 0.93 . ?
C57A C58 1.401(3) . ?
C57A C53A 1.412(3) . ?
C58 C51 1.369(3) . ?
C58 H58 0.93 . ?
C51 C52 1.412(3) . ?
C51 C5 1.473(3) . ?
C5 C6 1.426(3) . ?
C3A C3 1.371(3) . ?
C3 C2 1.385(3) . ?
C3 H3 0.93 . ?
C2 C21 1.487(3) . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?
C7 C6 1.340(3) . ?
C7 C71 1.498(3) . ?
C6 H6 0.93 . ?
C54 C53A 1.408(3) . ?
C54 H54 0.93 . ?
C53A C53 1.413(3) . ?
C53 C52 1.357(3) . ?
C53 H53 0.93 . ?
C52 H52 0.93 . ?

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
C5 N4 C3A 118.4(2) . . ?
C2 N1 N8 103.25(19) . . ?
C7 N8 N1 127.2(2) . . ?
C7 N8 C3A 120.24(19) . . ?
N1 N8 C3A 112.53(18) . . ?
C54 C55 C56 119.8(3) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C57 C56 C55 120.8(3) . . ?
C57 C56 H56 119.6 . . ?
C55 C56 H56 119.6 . . ?
C56 C57 C57A 120.8(3) . . ?
C56 C57 H57 119.6 . . ?
C57A C57 H57 119.6 . . ?
C58 C57A C53A 118.6(2) . . ?
C58 C57A C57 122.8(2) . . ?
C53A C57A C57 118.5(2) . . ?
C51 C58 C57A 123.2(2) . . ?
C51 C58 H58 118.4 . . ?
C57A C58 H58 118.4 . . ?
C58 C51 C52 117.6(2) . . ?
C58 C51 C5 122.4(2) . . ?
C52 C51 C5 120.0(2) . . ?
N4 C5 C6 120.8(2) . . ?
N4 C5 C51 117.4(2) . . ?
C6 C5 C51 121.8(2) . . ?
N4 C3A C3 133.3(2) . . ?
N4 C3A N8 121.5(2) . . ?
C3 C3A N8 105.1(2) . . ?
C3A C3 C2 106.2(2) . . ?
C3A C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
N1 C2 C3 112.9(2) . . ?
N1 C2 C21 118.9(2) . . ?
C3 C2 C21 128.1(2) . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.5 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?
C6 C7 N8 118.3(2) . . ?
C6 C7 C71 123.5(2) . . ?
N8 C7 C71 118.3(2) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C55 C54 C53A 121.6(3) . . ?
C55 C54 H54 119.2 . . ?
C53A C54 H54 119.2 . . ?
C54 C53A C57A 118.6(2) . . ?
C54 C53A C53 123.6(2) . . ?
C57A C53A C53 117.9(2) . . ?
C52 C53 C53A 121.8(2) . . ?
C52 C53 H53 119.1 . . ?
C53A C53 H53 119.1 . . ?
C53 C52 C51 120.9(2) . . ?
C53 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?
F72 C71 F73 106.9(2) . . ?
F72 C71 F71 106.4(2) . . ?
F73 C71 F71 106.9(2) . . ?
F72 C71 C7 113.1(2) . . ?
F73 C71 C7 112.1(2) . . ?
F71 C71 C7 110.9(2) . . ?

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
C2 N1 N8 C7 179.35(18) . . . . ?
C2 N1 N8 C3A -0.8(2) . . . . ?
C54 C55 C56 C57 -1.4(4) . . . . ?
C55 C56 C57 C57A 1.3(3) . . . . ?
C56 C57 C57A C58 179.7(2) . . . . ?
C56 C57 C57A C53A -0.3(3) . . . . ?
C53A C57A C58 C51 1.1(3) . . . . ?
C57 C57A C58 C51 -178.9(2) . . . . ?
C57A C58 C51 C52 -1.0(3) . . . . ?
C57A C58 C51 C5 179.2(2) . . . . ?
C3A N4 C5 C6 1.1(3) . . . . ?
C3A N4 C5 C51 -179.66(18) . . . . ?
C58 C51 C5 N4 171.24(19) . . . . ?
C52 C51 C5 N4 -8.6(3) . . . . ?
C58 C51 C5 C6 -9.6(3) . . . . ?
C52 C51 C5 C6 170.60(19) . . . . ?
C5 N4 C3A C3 178.2(2) . . . . ?
C5 N4 C3A N8 -0.9(3) . . . . ?
C7 N8 C3A N4 -0.2(3) . . . . ?
N1 N8 C3A N4 179.91(17) . . . . ?
C7 N8 C3A C3 -179.51(17) . . . . ?
N1 N8 C3A C3 0.6(2) . . . . ?
N4 C3A C3 C2 -179.4(2) . . . . ?
N8 C3A C3 C2 -0.2(2) . . . . ?
N8 N1 C2 C3 0.6(2) . . . . ?
N8 N1 C2 C21 -179.02(18) . . . . ?
C3A C3 C2 N1 -0.3(2) . . . . ?
C3A C3 C2 C21 179.3(2) . . . . ?
N1 N8 C7 C6 -179.18(19) . . . . ?
C3A N8 C7 C6 0.9(3) . . . . ?
N1 N8 C7 C71 1.7(3) . . . . ?
C3A N8 C7 C71 -178.2(2) . . . . ?
N8 C7 C6 C5 -0.7(3) . . . . ?
C71 C7 C6 C5 178.4(2) . . . . ?
N4 C5 C6 C7 -0.4(3) . . . . ?
C51 C5 C6 C7 -179.56(19) . . . . ?
C56 C55 C54 C53A 0.3(4) . . . . ?
C55 C54 C53A C57A 0.8(3) . . . . ?
C55 C54 C53A C53 -179.5(2) . . . . ?
C58 C57A C53A C54 179.28(19) . . . . ?
C57 C57A C53A C54 -0.8(3) . . . . ?
C58 C57A C53A C53 -0.5(3) . . . . ?
C57 C57A C53A C53 179.45(19) . . . . ?
C54 C53A C53 C52 -179.9(2) . . . . ?
C57A C53A C53 C52 -0.2(3) . . . . ?
C53A C53 C52 C51 0.3(3) . . . . ?
C58 C51 C52 C53 0.3(3) . . . . ?
C5 C51 C52 C53 -179.9(2) . . . . ?
C6 C7 C71 F72 120.9(2) . . . . ?
N8 C7 C71 F72 -60.1(3) . . . . ?
C6 C7 C71 F73 -118.0(2) . . . . ?
N8 C7 C71 F73 61.0(3) . . . . ?
C6 C7 C71 F71 1.4(3) . . . . ?
N8 C7 C71 F71 -179.56(19) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21c
_database_code_depnum_ccdc_archive 'CCDC 1056486'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T05:24:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2,5-dimethyl-7-(trichloromethyl)pyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C9 H8 Cl3 N3'
_chemical_formula_sum            'C9 H8 Cl3 N3'
_chemical_formula_weight         264.53
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3016(7)
_cell_length_b                   16.0564(11)
_cell_length_c                   6.8555(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.098(5)
_cell_angle_gamma                90
_cell_volume                     1132.29(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2957
_cell_measurement_theta_min      3.219
_cell_measurement_theta_max      25.224

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.985

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_number            12894
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         28.8
_diffrn_reflns_theta_full        28.8
_diffrn_measured_fraction_theta_full 0.94
_diffrn_measured_fraction_theta_max 0.94
_reflns_number_total             2780
_reflns_number_gt                1320
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2780
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.1958
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_restrained_S_all      0.878
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.138

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.37617(11) -0.07449(6) 0.23859(16) 0.0573(4) Uani 1 1 d . . .
Cl2 Cl 0.17794(12) 0.00921(7) 0.00478(19) 0.0664(4) Uani 1 1 d . . .
Cl3 Cl 0.17295(12) 0.01035(7) 0.4265(2) 0.0667(4) Uani 1 1 d . . .
C7 C 0.3541(4) 0.0949(2) 0.2346(5) 0.0412(9) Uani 1 1 d . . .
N4 N 0.4881(3) 0.24803(18) 0.2483(4) 0.0433(8) Uani 1 1 d . . .
C3A C 0.3568(4) 0.2447(2) 0.2332(5) 0.0408(9) Uani 1 1 d . . .
C71 C 0.2763(4) 0.0152(3) 0.2265(6) 0.0464(10) Uani 1 1 d . . .
C5 C 0.5508(4) 0.1773(3) 0.2566(6) 0.0448(9) Uani 1 1 d . . .
C6 C 0.4859(4) 0.0992(3) 0.2504(6) 0.0474(10) Uani 1 1 d . . .
H6 H 0.5344 0.0504 0.2571 0.057 Uiso 1 1 calc R . .
C3 C 0.2638(4) 0.3051(3) 0.2219(6) 0.0515(10) Uani 1 1 d . . .
H3 H 0.2775 0.3623 0.2234 0.062 Uiso 1 1 calc R . .
C51 C 0.6961(4) 0.1810(3) 0.2741(7) 0.0614(12) Uani 1 1 d . . .
H51A H 0.7237 0.2381 0.2763 0.092 Uiso 1 1 calc R . .
H51B H 0.7309 0.1532 0.1645 0.092 Uiso 1 1 calc R . .
H51C H 0.7269 0.1541 0.3928 0.092 Uiso 1 1 calc R . .
C2 C 0.1456(4) 0.2649(3) 0.2078(6) 0.0553(11) Uani 1 1 d . . .
C21 C 0.0123(4) 0.3018(3) 0.1922(8) 0.0768(16) Uani 1 1 d . . .
H21A H -0.0511 0.258 0.1858 0.115 Uiso 1 1 calc R . .
H21B H 0.0028 0.3352 0.0761 0.115 Uiso 1 1 calc R . .
H21C H -0.0004 0.3359 0.3045 0.115 Uiso 1 1 calc R . .
N1 N 0.1578(3) 0.1810(2) 0.2099(5) 0.0520(9) Uani 1 1 d . . .
N8 N 0.2887(3) 0.1692(2) 0.2259(5) 0.0435(8) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Cl1 C71 1.769(4) . ?
Cl1 N4 13.280(3) 2_655 ?
Cl2 C71 1.783(4) . ?
Cl2 N1 3.108(4) . ?
Cl3 C71 1.782(4) . ?
Cl3 N1 3.117(4) . ?
C7 C6 1.358(5) . ?
C7 N8 1.370(5) . ?
C7 C71 1.510(5) . ?
N4 C5 1.306(5) . ?
N4 C3A 1.352(5) . ?
C3A C3 1.363(5) . ?
C3A N8 1.400(5) . ?
C5 C6 1.420(5) . ?
C5 C51 1.496(6) . ?
C6 H6 0.93 . ?
C3 C2 1.376(6) . ?
C3 H3 0.93 . ?
C51 H51A 0.96 . ?
C51 H51B 0.96 . ?
C51 H51C 0.96 . ?
C2 N1 1.353(5) . ?
C2 C21 1.494(6) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
N1 N8 1.360(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
C71 Cl1 N4 41.56(14) . 2_655 ?
C71 Cl2 N1 67.38(15) . . ?
C71 Cl3 N1 67.16(15) . . ?
C6 C7 N8 116.5(3) . . ?
C6 C7 C71 125.0(4) . . ?
N8 C7 C71 118.5(3) . . ?
C5 N4 C3A 117.3(3) . . ?
N4 C3A C3 132.3(3) . . ?
N4 C3A N8 122.3(3) . . ?
C3 C3A N8 105.3(3) . . ?
C7 C71 Cl1 112.5(3) . . ?
C7 C71 Cl3 110.3(3) . . ?
Cl1 C71 Cl3 107.4(2) . . ?
C7 C71 Cl2 110.7(3) . . ?
Cl1 C71 Cl2 107.4(2) . . ?
Cl3 C71 Cl2 108.5(2) . . ?
N4 C5 C6 122.4(4) . . ?
N4 C5 C51 117.4(4) . . ?
C6 C5 C51 120.3(4) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C3A C3 C2 106.7(4) . . ?
C3A C3 H3 126.7 . . ?
C2 C3 H3 126.7 . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N1 C2 C3 112.6(4) . . ?
N1 C2 C21 118.7(4) . . ?
C3 C2 C21 128.7(4) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N1 N8 103.3(3) . . ?
C2 N1 Cl2 152.5(3) . . ?
N8 N1 Cl2 79.8(2) . . ?
C2 N1 Cl3 152.0(3) . . ?
N8 N1 Cl3 79.3(2) . . ?
Cl2 N1 Cl3 55.42(7) . . ?
N1 N8 C7 127.5(3) . . ?
N1 N8 C3A 112.0(3) . . ?
C7 N8 C3A 120.5(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
C5 N4 C3A C3 179.8(4) . . . . ?
C5 N4 C3A N8 -0.2(5) . . . . ?
C6 C7 C71 Cl1 -0.3(5) . . . . ?
N8 C7 C71 Cl1 179.8(3) . . . . ?
C6 C7 C71 Cl3 119.5(4) . . . . ?
N8 C7 C71 Cl3 -60.4(4) . . . . ?
C6 C7 C71 Cl2 -120.4(4) . . . . ?
N8 C7 C71 Cl2 59.7(4) . . . . ?
N4 Cl1 C71 C7 0.22(16) 2_655 . . . ?
N4 Cl1 C71 Cl3 -121.3(3) 2_655 . . . ?
N4 Cl1 C71 Cl2 122.2(3) 2_655 . . . ?
N1 Cl3 C71 C7 47.8(2) . . . . ?
N1 Cl3 C71 Cl1 170.7(2) . . . . ?
N1 Cl3 C71 Cl2 -73.58(19) . . . . ?
N1 Cl2 C71 C7 -47.4(2) . . . . ?
N1 Cl2 C71 Cl1 -170.4(2) . . . . ?
N1 Cl2 C71 Cl3 73.79(19) . . . . ?
C3A N4 C5 C6 0.0(5) . . . . ?
C3A N4 C5 C51 -179.8(4) . . . . ?
N8 C7 C6 C5 -0.2(6) . . . . ?
C71 C7 C6 C5 179.9(4) . . . . ?
N4 C5 C6 C7 0.2(6) . . . . ?
C51 C5 C6 C7 180.0(4) . . . . ?
N4 C3A C3 C2 179.8(4) . . . . ?
N8 C3A C3 C2 -0.2(4) . . . . ?
C3A C3 C2 N1 0.2(5) . . . . ?
C3A C3 C2 C21 179.9(4) . . . . ?
C3 C2 N1 N8 0.0(5) . . . . ?
C21 C2 N1 N8 -179.8(4) . . . . ?
C3 C2 N1 Cl2 -93.5(6) . . . . ?
C21 C2 N1 Cl2 86.8(7) . . . . ?
C3 C2 N1 Cl3 92.3(6) . . . . ?
C21 C2 N1 Cl3 -87.4(6) . . . . ?
C71 Cl2 N1 C2 144.1(6) . . . . ?
C71 Cl2 N1 N8 44.8(2) . . . . ?
C71 Cl2 N1 Cl3 -39.22(14) . . . . ?
C71 Cl3 N1 C2 -143.9(6) . . . . ?
C71 Cl3 N1 N8 -45.5(2) . . . . ?
C71 Cl3 N1 Cl2 39.32(15) . . . . ?
C2 N1 N8 C7 179.9(4) . . . . ?
Cl2 N1 N8 C7 -28.0(3) . . . . ?
Cl3 N1 N8 C7 28.4(3) . . . . ?
C2 N1 N8 C3A -0.1(4) . . . . ?
Cl2 N1 N8 C3A 152.0(3) . . . . ?
Cl3 N1 N8 C3A -151.6(3) . . . . ?
C6 C7 N8 N1 179.9(4) . . . . ?
C71 C7 N8 N1 -0.1(5) . . . . ?
C6 C7 N8 C3A 0.0(5) . . . . ?
C71 C7 N8 C3A 179.9(3) . . . . ?
N4 C3A N8 N1 -179.8(3) . . . . ?
C3 C3A N8 N1 0.2(4) . . . . ?
N4 C3A N8 C7 0.2(5) . . . . ?
C3 C3A N8 C7 -179.8(3) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21c
_database_code_depnum_ccdc_archive 'CCDC 1056487'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T05:40:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '2-methyl-7-tricholoromethyl-5-propylpyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C11 H12 Cl3 N3'
_chemical_formula_sum            'C11 H12 Cl3 N3'
_chemical_formula_weight         292.59
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2451(8)
_cell_length_b                   5.8697(4)
_cell_length_c                   20.9201(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.896(5)
_cell_angle_gamma                90
_cell_volume                     1334.43(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2847
_cell_measurement_theta_min      2.373
_cell_measurement_theta_max      25.739

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       tabular
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.158
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_T_max  0.9

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_number            13171
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_full        28.4
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3314
_reflns_number_gt                2434
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0743P)²+0.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.1
_refine_ls_restrained_S_all      1.1
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.46
_refine_diff_density_rms         0.231

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.91692(6) -0.14936(9) 0.57495(3) 0.05703(19) Uani 1 1 d . . .
Cl2 Cl 0.83536(6) 0.30649(9) 0.54383(3) 0.05688(19) Uani 1 1 d . . .
Cl3 Cl 0.66174(6) -0.04343(11) 0.55879(3) 0.0636(2) Uani 1 1 d . . .
N3 N 0.69101(17) -0.1309(3) 0.31954(9) 0.0500(4) Uani 1 1 d . . .
N1 N 0.60811(18) 0.2636(3) 0.43063(10) 0.0510(5) Uani 1 1 d . . .
C2 C 0.5326(2) 0.3275(4) 0.37221(13) 0.0539(6) Uani 1 1 d . . .
N8 N 0.67233(15) 0.0869(3) 0.41395(9) 0.0428(4) Uani 1 1 d . . .
C3A C 0.63798(19) 0.0396(3) 0.34630(11) 0.0458(5) Uani 1 1 d . . .
C6 C 0.81499(19) -0.2073(3) 0.42890(10) 0.0427(5) Uani 1 1 d . . .
H6 H 0.8767 -0.2958 0.4556 0.051 Uiso 1 1 calc R . .
C5 C 0.7768(2) -0.2511(4) 0.35967(10) 0.0456(5) Uani 1 1 d . . .
C7 C 0.76261(18) -0.0384(3) 0.45624(10) 0.0397(4) Uani 1 1 d . . .
C8 C 0.79236(19) 0.0163(3) 0.52895(11) 0.0443(5) Uani 1 1 d . . .
C51 C 0.8385(2) -0.4434(4) 0.33276(12) 0.0561(6) Uani 1 1 d . . .
H51A H 0.9265 -0.4158 0.3454 0.067 Uiso 1 1 calc R . .
H51B H 0.824 -0.5829 0.3544 0.067 Uiso 1 1 calc R . .
C3 C 0.5473(2) 0.1960(4) 0.31978(13) 0.0565(6) Uani 1 1 d . . .
H3 H 0.5045 0.2103 0.2756 0.068 Uiso 1 1 calc R . .
C52 C 0.8000(3) -0.4824(5) 0.25938(13) 0.0647(7) Uani 1 1 d . . .
H52A H 0.8164 -0.3464 0.2368 0.078 Uiso 1 1 calc R . .
H52B H 0.7121 -0.5115 0.2457 0.078 Uiso 1 1 calc R . .
C1 C 0.4464(3) 0.5234(5) 0.37172(16) 0.0736(8) Uani 1 1 d . . .
H1A H 0.457 0.5788 0.416 0.11 Uiso 1 1 calc R . .
H1B H 0.3631 0.4731 0.3545 0.11 Uiso 1 1 calc R . .
H1C H 0.4641 0.6433 0.3444 0.11 Uiso 1 1 calc R . .
C53 C 0.8684(3) -0.6827(5) 0.23984(15) 0.0782(8) Uani 1 1 d . . .
H53A H 0.8419 -0.7043 0.1928 0.117 Uiso 1 1 calc R . .
H53B H 0.8513 -0.8177 0.2618 0.117 Uiso 1 1 calc R . .
H53C H 0.9552 -0.6527 0.2526 0.117 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Cl1 C8 1.772(2) . ?
Cl2 C8 1.776(2) . ?
Cl3 C8 1.772(2) . ?
N3 C5 1.311(3) . ?
N3 C3A 1.357(3) . ?
N1 C2 1.350(3) . ?
N1 N8 1.359(2) . ?
C2 C3 1.385(4) . ?
C2 C1 1.502(3) . ?
N8 C7 1.376(2) . ?
N8 C3A 1.396(3) . ?
C3A C3 1.378(3) . ?
C6 C7 1.353(3) . ?
C6 C5 1.424(3) . ?
C6 H6 0.93 . ?
C5 C51 1.507(3) . ?
C7 C8 1.506(3) . ?
C51 C52 1.502(3) . ?
C51 H51A 0.97 . ?
C51 H51B 0.97 . ?
C3 H3 0.93 . ?
C52 C53 1.518(4) . ?
C52 H52A 0.97 . ?
C52 H52B 0.97 . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C53 H53A 0.96 . ?
C53 H53B 0.96 . ?
C53 H53C 0.96 . ?

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
C5 N3 C3A 117.53(19) . . ?
C2 N1 N8 103.38(19) . . ?
N1 C2 C3 112.8(2) . . ?
N1 C2 C1 118.2(2) . . ?
C3 C2 C1 129.0(2) . . ?
N1 N8 C7 126.57(18) . . ?
N1 N8 C3A 112.65(16) . . ?
C7 N8 C3A 120.78(17) . . ?
N3 C3A C3 133.1(2) . . ?
N3 C3A N8 121.90(18) . . ?
C3 C3A N8 105.0(2) . . ?
C7 C6 C5 120.82(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N3 C5 C6 122.3(2) . . ?
N3 C5 C51 119.85(19) . . ?
C6 C5 C51 117.89(18) . . ?
C6 C7 N8 116.71(18) . . ?
C6 C7 C8 125.15(18) . . ?
N8 C7 C8 118.11(18) . . ?
C7 C8 Cl1 111.77(15) . . ?
C7 C8 Cl3 108.93(14) . . ?
Cl1 C8 Cl3 108.12(11) . . ?
C7 C8 Cl2 111.19(14) . . ?
Cl1 C8 Cl2 106.83(11) . . ?
Cl3 C8 Cl2 109.94(12) . . ?
C52 C51 C5 117.1(2) . . ?
C52 C51 H51A 108 . . ?
C5 C51 H51A 108 . . ?
C52 C51 H51B 108 . . ?
C5 C51 H51B 108 . . ?
H51A C51 H51B 107.3 . . ?
C3A C3 C2 106.2(2) . . ?
C3A C3 H3 126.9 . . ?
C2 C3 H3 126.9 . . ?
C51 C52 C53 111.1(2) . . ?
C51 C52 H52A 109.4 . . ?
C53 C52 H52A 109.4 . . ?
C51 C52 H52B 109.4 . . ?
C53 C52 H52B 109.4 . . ?
H52A C52 H52B 108 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?

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
N8 N1 C2 C3 0.3(3) . . . . ?
N8 N1 C2 C1 -179.8(2) . . . . ?
C2 N1 N8 C7 179.64(19) . . . . ?
C2 N1 N8 C3A -0.1(2) . . . . ?
C5 N3 C3A C3 -179.9(2) . . . . ?
C5 N3 C3A N8 -0.1(3) . . . . ?
N1 N8 C3A N3 -179.90(19) . . . . ?
C7 N8 C3A N3 0.3(3) . . . . ?
N1 N8 C3A C3 -0.1(2) . . . . ?
C7 N8 C3A C3 -179.84(18) . . . . ?
C3A N3 C5 C6 -0.3(3) . . . . ?
C3A N3 C5 C51 179.7(2) . . . . ?
C7 C6 C5 N3 0.5(3) . . . . ?
C7 C6 C5 C51 -179.5(2) . . . . ?
C5 C6 C7 N8 -0.3(3) . . . . ?
C5 C6 C7 C8 177.46(18) . . . . ?
N1 N8 C7 C6 -179.8(2) . . . . ?
C3A N8 C7 C6 -0.1(3) . . . . ?
N1 N8 C7 C8 2.3(3) . . . . ?
C3A N8 C7 C8 -178.01(18) . . . . ?
C6 C7 C8 Cl1 6.0(3) . . . . ?
N8 C7 C8 Cl1 -176.30(14) . . . . ?
C6 C7 C8 Cl3 -113.4(2) . . . . ?
N8 C7 C8 Cl3 64.29(19) . . . . ?
C6 C7 C8 Cl2 125.27(19) . . . . ?
N8 C7 C8 Cl2 -57.0(2) . . . . ?
N3 C5 C51 C52 1.9(3) . . . . ?
C6 C5 C51 C52 -178.1(2) . . . . ?
N3 C3A C3 C2 -180.0(2) . . . . ?
N8 C3A C3 C2 0.2(3) . . . . ?
N1 C2 C3 C3A -0.3(3) . . . . ?
C1 C2 C3 C3A 179.8(2) . . . . ?
C5 C51 C52 C53 -179.2(2) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21
_database_code_depnum_ccdc_archive 'CCDC 1056488'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T05:55:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '3-bromo-2-methyl-7-tricholomethylpyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C8 H5 Br Cl3 N3'
_chemical_formula_sum            'C8 H5 Br Cl3 N3'
_chemical_formula_weight         329.41
_chemical_melting_point          none
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  P2yb
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4329(2)
_cell_length_b                   6.7756(2)
_cell_length_c                   11.1667(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.2760(10)
_cell_angle_gamma                90
_cell_volume                     562.37(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1790
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      26.994

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.162
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.334
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  0.496

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_number            5503
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         28.4
_diffrn_reflns_theta_full        28.4
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2653
_reflns_number_gt                2142
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0407P)²+0.8107P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.008
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(9)
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br Br -0.01108(6) 0.3475(4) 1.17191(3) 0.04823(15) Uani 1 1 d . . .
Cl2 Cl 0.3582(6) 0.5636(2) 0.6313(3) 0.0573(10) Uani 1 1 d . . .
Cl3 Cl 0.3591(6) 0.1324(2) 0.6317(3) 0.0573(10) Uani 1 1 d . . .
Cl1 Cl 0.13588(19) 0.3464(9) 0.46806(9) 0.0695(4) Uani 1 1 d . . .
N8 N 0.1273(3) 0.3449(15) 0.8265(2) 0.0267(5) Uani 1 1 d . . .
N4 N -0.1813(4) 0.3524(19) 0.8932(3) 0.0377(7) Uani 1 1 d . . .
N1 N 0.2969(4) 0.345(2) 0.8722(2) 0.0309(6) Uani 1 1 d . . .
C3A C -0.0026(4) 0.344(2) 0.9162(3) 0.0292(7) Uani 1 1 d . . .
C7 C 0.0771(5) 0.349(2) 0.7083(3) 0.0330(7) Uani 1 1 d . . .
C3 C 0.0936(4) 0.347(2) 1.0213(3) 0.0296(7) Uani 1 1 d . . .
C71 C 0.2239(5) 0.349(2) 0.6160(3) 0.0416(8) Uani 1 1 d . . .
C2 C 0.2744(4) 0.347(2) 0.9918(3) 0.0301(6) Uani 1 1 d . . .
C21 C 0.4328(5) 0.350(3) 1.0742(3) 0.0455(9) Uani 1 1 d . . .
H1A H 0.5415 0.3474 1.0281 0.068 Uiso 1 1 calc R . .
H1B H 0.429 0.2356 1.1252 0.068 Uiso 1 1 calc R . .
H1C H 0.4299 0.4669 1.1222 0.068 Uiso 1 1 calc R . .
C5 C -0.2258(5) 0.350(3) 0.7792(4) 0.0481(10) Uani 1 1 d . . .
H5 H -0.3476 0.3496 0.7599 0.058 Uiso 1 1 calc R . .
C6 C -0.1017(5) 0.349(2) 0.6842(3) 0.0421(9) Uani 1 1 d . . .
H6 H -0.1424 0.349 0.6054 0.05 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Br C3 1.857(3) . ?
Cl2 C71 1.773(14) . ?
Cl3 C71 1.786(14) . ?
Cl1 C71 1.774(4) . ?
N8 N1 1.358(4) . ?
N8 C7 1.370(4) . ?
N8 C3A 1.394(4) . ?
N4 C5 1.313(5) . ?
N4 C3A 1.353(5) . ?
N1 C2 1.347(4) . ?
C3A C3 1.371(5) . ?
C7 C6 1.354(5) . ?
C7 C71 1.505(5) . ?
C3 C2 1.385(5) . ?
C2 C21 1.491(5) . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?
C5 C6 1.409(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?

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
N1 N8 C7 127.6(3) . . ?
N1 N8 C3A 112.0(2) . . ?
C7 N8 C3A 120.4(3) . . ?
C5 N4 C3A 115.2(3) . . ?
C2 N1 N8 104.7(2) . . ?
N4 C3A C3 132.0(3) . . ?
N4 C3A N8 123.1(3) . . ?
C3 C3A N8 104.8(3) . . ?
C6 C7 N8 117.0(3) . . ?
C6 C7 C71 125.4(3) . . ?
N8 C7 C71 117.7(3) . . ?
C3A C3 C2 107.4(3) . . ?
C3A C3 Br 123.8(3) . . ?
C2 C3 Br 128.8(2) . . ?
C7 C71 Cl2 110.1(9) . . ?
C7 C71 Cl1 111.8(3) . . ?
Cl2 C71 Cl1 107.6(6) . . ?
C7 C71 Cl3 110.1(8) . . ?
Cl2 C71 Cl3 110.4(2) . . ?
Cl1 C71 Cl3 106.8(6) . . ?
N1 C2 C3 111.2(3) . . ?
N1 C2 C21 120.7(3) . . ?
C3 C2 C21 128.1(3) . . ?
C2 C21 H1A 109.5 . . ?
C2 C21 H1B 109.4 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.5 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?
N4 C5 C6 124.5(4) . . ?
N4 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?

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
C7 N8 N1 C2 177.8(13) . . . . ?
C3A N8 N1 C2 -0.8(15) . . . . ?
C5 N4 C3A C3 178.6(16) . . . . ?
C5 N4 C3A N8 3(2) . . . . ?
N1 N8 C3A N4 177.2(13) . . . . ?
C7 N8 C3A N4 -1(2) . . . . ?
N1 N8 C3A C3 0.8(15) . . . . ?
C7 N8 C3A C3 -177.8(11) . . . . ?
N1 N8 C7 C6 -179.5(14) . . . . ?
C3A N8 C7 C6 -1(2) . . . . ?
N1 N8 C7 C71 2(2) . . . . ?
C3A N8 C7 C71 -179.8(12) . . . . ?
N4 C3A C3 C2 -176.4(16) . . . . ?
N8 C3A C3 C2 -0.6(15) . . . . ?
N4 C3A C3 Br 4(2) . . . . ?
N8 C3A C3 Br -179.8(9) . . . . ?
C6 C7 C71 Cl2 118.9(14) . . . . ?
N8 C7 C71 Cl2 -62.4(14) . . . . ?
C6 C7 C71 Cl1 -1(2) . . . . ?
N8 C7 C71 Cl1 178.1(10) . . . . ?
C6 C7 C71 Cl3 -119.2(14) . . . . ?
N8 C7 C71 Cl3 59.5(14) . . . . ?
N8 N1 C2 C3 0.4(15) . . . . ?
N8 N1 C2 C21 -179.7(14) . . . . ?
C3A C3 C2 N1 0.1(16) . . . . ?
Br C3 C2 N1 179.4(10) . . . . ?
C3A C3 C2 C21 -179.8(16) . . . . ?
Br C3 C2 C21 -1(2) . . . . ?
C3A N4 C5 C6 -3(2) . . . . ?
N8 C7 C6 C5 2(2) . . . . ?
C71 C7 C6 C5 -179.8(14) . . . . ?
N4 C5 C6 C7 0(2) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p21
_database_code_depnum_ccdc_archive 'CCDC 1056489'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T06:11:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'3-bromo -2,5-dimethyl-7-trichoromethylpyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C9 H7 Br Cl3 N3'
_chemical_formula_sum            'C9 H7 Br Cl3 N3'
_chemical_formula_weight         343.44
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  P2yb
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6363(3)
_cell_length_b                   6.9353(2)
_cell_length_c                   9.8541(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.240(2)
_cell_angle_gamma                90
_cell_volume                     613.82(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3036
_cell_measurement_theta_min      2.533
_cell_measurement_theta_max      26.447

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.858
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.166
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.975
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.255
_exptl_absorpt_correction_T_max  0.517

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.029
_diffrn_reflns_number            6092
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2998
_reflns_number_gt                2292
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.3564P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.388
_refine_ls_shift/su_mean         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.122

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br Br 0.67768(5) 0.2598(5) 0.89936(5) 0.0661(2) Uani 1 1 d . . .
Cl1 Cl 0.06548(12) 0.2592(11) 0.10034(10) 0.0646(3) Uani 1 1 d . . .
Cl3 Cl 0.0339(4) 0.4718(2) 0.3388(5) 0.0620(9) Uani 1 1 d . . .
Cl2 Cl 0.0275(4) 0.0539(2) 0.3342(4) 0.0586(8) Uani 1 1 d . . .
N2 N 0.3306(3) 0.2672(16) 0.5213(3) 0.0296(6) Uani 1 1 d . . .
N4 N 0.5863(3) 0.2657(19) 0.5340(3) 0.0381(7) Uani 1 1 d . . .
N1 N 0.2505(3) 0.2577(18) 0.6096(3) 0.0354(7) Uani 1 1 d . . .
C7 C 0.2768(3) 0.262(2) 0.3712(3) 0.0303(6) Uani 1 1 d . . .
C6 C 0.3790(4) 0.266(2) 0.3062(4) 0.0359(9) Uani 1 1 d . . .
H6 H 0.3474 0.2729 0.2052 0.043 Uiso 1 1 calc R . .
C5 C 0.5349(4) 0.260(2) 0.3907(4) 0.0361(7) Uani 1 1 d . . .
C51 C 0.6473(5) 0.260(2) 0.3185(5) 0.0493(10) Uani 1 1 d . . .
H51A H 0.7457 0.2611 0.3914 0.074 Uiso 1 1 calc R . .
H51B H 0.6337 0.3733 0.2587 0.074 Uiso 1 1 calc R . .
H51C H 0.6346 0.1472 0.2591 0.074 Uiso 1 1 calc R . .
C3 C 0.4978(4) 0.256(2) 0.7429(4) 0.0387(9) Uani 1 1 d . . .
C3A C 0.4838(4) 0.256(2) 0.5990(4) 0.0332(8) Uani 1 1 d . . .
C71 C 0.1102(4) 0.257(2) 0.2913(4) 0.0392(9) Uani 1 1 d . . .
C2 C 0.3537(4) 0.262(2) 0.7447(4) 0.0384(8) Uani 1 1 d . . .
C21 C 0.3086(5) 0.261(3) 0.8749(4) 0.0542(11) Uani 1 1 d . . .
H1A H 0.2021 0.2677 0.8436 0.081 Uiso 1 1 calc R . .
H1B H 0.3515 0.3708 0.9352 0.081 Uiso 1 1 calc R . .
H1C H 0.3433 0.1451 0.9294 0.081 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Br C3 1.856(3) . ?
Cl1 C71 1.772(4) . ?
Cl3 C71 1.799(13) . ?
Cl2 C71 1.741(13) . ?
N2 N1 1.357(4) . ?
N2 C7 1.379(4) . ?
N2 C3A 1.397(4) . ?
N4 C5 1.317(5) . ?
N4 C3A 1.359(5) . ?
N1 C2 1.343(5) . ?
C7 C6 1.356(5) . ?
C7 C71 1.511(4) . ?
C6 C5 1.430(5) . ?
C6 H6 0.93 . ?
C5 C51 1.496(5) . ?
C51 H51A 0.96 . ?
C51 H51B 0.96 . ?
C51 H51C 0.96 . ?
C3 C3A 1.375(5) . ?
C3 C2 1.396(6) . ?
C2 C21 1.496(5) . ?
C21 H1A 0.96 . ?
C21 H1B 0.96 . ?
C21 H1C 0.96 . ?

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
N1 N2 C7 127.3(3) . . ?
N1 N2 C3A 112.3(3) . . ?
C7 N2 C3A 119.9(3) . . ?
C5 N4 C3A 116.7(3) . . ?
C2 N1 N2 104.2(3) . . ?
C6 C7 N2 116.8(3) . . ?
C6 C7 C71 124.8(3) . . ?
N2 C7 C71 118.3(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.6 . . ?
N4 C5 C6 122.1(3) . . ?
N4 C5 C51 117.0(3) . . ?
C6 C5 C51 120.8(3) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.6 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.3 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C3A C3 C2 106.6(3) . . ?
C3A C3 Br 124.7(3) . . ?
C2 C3 Br 128.5(3) . . ?
N4 C3A C3 132.0(3) . . ?
N4 C3A N2 122.9(3) . . ?
C3 C3A N2 104.7(3) . . ?
C7 C71 Cl2 112.7(9) . . ?
C7 C71 Cl1 110.9(2) . . ?
Cl2 C71 Cl1 108.0(6) . . ?
C7 C71 Cl3 107.6(8) . . ?
Cl2 C71 Cl3 109.9(2) . . ?
Cl1 C71 Cl3 107.6(7) . . ?
N1 C2 C3 111.7(3) . . ?
N1 C2 C21 120.6(3) . . ?
C3 C2 C21 127.6(4) . . ?
C2 C21 H1A 109.4 . . ?
C2 C21 H1B 109.3 . . ?
H1A C21 H1B 109.5 . . ?
C2 C21 H1C 109.7 . . ?
H1A C21 H1C 109.5 . . ?
H1B C21 H1C 109.5 . . ?

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
C7 N2 N1 C2 178.0(15) . . . . ?
C3A N2 N1 C2 6.6(14) . . . . ?
N1 N2 C7 C6 -177.5(12) . . . . ?
C3A N2 C7 C6 -7(2) . . . . ?
N1 N2 C7 C71 4(2) . . . . ?
C3A N2 C7 C71 174.9(12) . . . . ?
N2 C7 C6 C5 5(2) . . . . ?
C71 C7 C6 C5 -176.5(14) . . . . ?
C3A N4 C5 C6 7(2) . . . . ?
C3A N4 C5 C51 -177.2(12) . . . . ?
C7 C6 C5 N4 -6(2) . . . . ?
C7 C6 C5 C51 178.7(14) . . . . ?
C5 N4 C3A C3 178.9(16) . . . . ?
C5 N4 C3A N2 -9(2) . . . . ?
C2 C3 C3A N4 174.5(14) . . . . ?
Br C3 C3A N4 -2(2) . . . . ?
C2 C3 C3A N2 1.2(16) . . . . ?
Br C3 C3A N2 -175.8(10) . . . . ?
N1 N2 C3A N4 -179.1(11) . . . . ?
C7 N2 C3A N4 9(2) . . . . ?
N1 N2 C3A C3 -4.9(15) . . . . ?
C7 N2 C3A C3 -177.1(13) . . . . ?
C6 C7 C71 Cl2 120.7(13) . . . . ?
N2 C7 C71 Cl2 -61.0(15) . . . . ?
C6 C7 C71 Cl1 -1(2) . . . . ?
N2 C7 C71 Cl1 177.8(11) . . . . ?
C6 C7 C71 Cl3 -118.0(13) . . . . ?
N2 C7 C71 Cl3 60.3(14) . . . . ?
N2 N1 C2 C3 -5.8(15) . . . . ?
N2 N1 C2 C21 177.9(14) . . . . ?
C3A C3 C2 N1 2.9(17) . . . . ?
Br C3 C2 N1 179.8(11) . . . . ?
C3A C3 C2 C21 178.9(16) . . . . ?
Br C3 C2 C21 -4(3) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1056490'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2015-03-25T06:20:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'2-methyl-5-p-tolyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine'
;
_chemical_name_common            pyrazolo[1,5-a]pyrimidine
_chemical_formula_moiety         'C15 H12 F3 N3'
_chemical_formula_sum            'C15 H12 F3 N3'
_chemical_formula_weight         291.28
_chemical_melting_point          NONE

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8715(2)
_cell_length_b                   11.2655(5)
_cell_length_c                   13.5584(6)
_cell_angle_alpha                110.225(3)
_cell_angle_beta                 96.808(3)
_cell_angle_gamma                99.835(3)
_cell_volume                     675.13(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3097
_cell_measurement_theta_min      2.999
_cell_measurement_theta_max      24.602

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size.
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_number            16787
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         29.66
_diffrn_reflns_theta_full        29.66
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             3757
_reflns_number_gt                2200
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Shekdrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1373P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1859
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          2.723
_refine_ls_shift/su_mean         0.071
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
N4 N -0.1394(3) 0.64066(13) 0.15770(10) 0.0450(4) Uani 1 1 d . . .
C51 C 0.2300(3) 0.60519(16) 0.27096(13) 0.0445(4) Uani 1 1 d . . .
C5 C 0.0594(3) 0.69036(15) 0.24464(12) 0.0439(4) Uani 1 1 d . . .
N8 N -0.2414(3) 0.85107(14) 0.19702(11) 0.0489(4) Uani 1 1 d . . .
C3A C -0.2916(3) 0.71924(16) 0.13247(13) 0.0455(4) Uani 1 1 d . . .
C7 C -0.0385(4) 0.90320(17) 0.28742(15) 0.0529(4) Uani 1 1 d . . .
N1 N -0.4126(3) 0.91420(15) 0.15725(13) 0.0574(4) Uani 1 1 d . . .
C6 C 0.1128(4) 0.82474(17) 0.31325(14) 0.0513(4) Uani 1 1 d . . .
H6 H 0.2513 0.8577 0.3753 0.062 Uiso 1 1 calc R . .
C56 C 0.2275(4) 0.48482(18) 0.19512(14) 0.0539(5) Uani 1 1 d . . .
H56 H 0.1161 0.4574 0.1272 0.065 Uiso 1 1 calc R . .
C55 C 0.3881(4) 0.40513(18) 0.21905(15) 0.0584(5) Uani 1 1 d . . .
H55 H 0.3812 0.3246 0.1669 0.07 Uiso 1 1 calc R . .
C52 C 0.4029(4) 0.64262(19) 0.37086(15) 0.0598(5) Uani 1 1 d . . .
H52 H 0.4098 0.723 0.4233 0.072 Uiso 1 1 calc R . .
C54 C 0.5592(4) 0.44188(19) 0.31866(15) 0.0552(5) Uani 1 1 d . . .
C3 C -0.5080(4) 0.69987(18) 0.04974(14) 0.0528(4) Uani 1 1 d . . .
H3 H -0.5939 0.622 -0.0068 0.063 Uiso 1 1 calc R . .
C2 C -0.5725(4) 0.81987(18) 0.06755(15) 0.0534(5) Uani 1 1 d . . .
C53 C 0.5644(4) 0.5626(2) 0.39351(16) 0.0643(5) Uani 1 1 d . . .
H53 H 0.6795 0.5906 0.4608 0.077 Uiso 1 1 calc R . .
C8 C 0.7333(5) 0.3539(2) 0.34296(18) 0.0713(6) Uani 1 1 d . . .
H8A H 0.7037 0.2755 0.2809 0.107 Uiso 1 1 calc R . .
H8B H 0.6769 0.3328 0.4015 0.107 Uiso 1 1 calc R . .
H8C H 0.9306 0.397 0.362 0.107 Uiso 1 1 calc R . .
C71 C 0.0064(5) 1.0447(2) 0.3533(2) 0.0726(6) Uani 1 1 d . . .
C21 C -0.7881(4) 0.8562(2) 0.00177(17) 0.0704(6) Uani 1 1 d . . .
H21A H -0.7829 0.9471 0.0353 0.106 Uiso 1 1 calc R . .
H21B H -0.9738 0.8064 -0.0036 0.106 Uiso 1 1 calc R . .
H21C H -0.7458 0.8385 -0.0686 0.106 Uiso 1 1 calc R . .
F3 F -0.2262(3) 1.07477(12) 0.38784(11) 0.0909(5) Uani 1 1 d . . .
F1 F 0.2074(3) 1.07987(12) 0.43936(12) 0.1024(6) Uani 1 1 d . . .
F2 F 0.0852(3) 1.11908(12) 0.29937(14) 0.1019(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
N4 C5 1.315(2) . ?
N4 C3A 1.350(2) . ?
C51 C56 1.387(2) . ?
C51 C52 1.391(2) . ?
C51 C5 1.476(2) . ?
C5 C6 1.435(2) . ?
N8 C7 1.357(2) . ?
N8 N1 1.3611(19) . ?
N8 C3A 1.399(2) . ?
C3A C3 1.375(2) . ?
C7 C6 1.350(2) . ?
C7 C71 1.496(3) . ?
N1 C2 1.347(2) . ?
C6 H6 0.93 . ?
C56 C55 1.380(2) . ?
C56 H56 0.93 . ?
C55 C54 1.385(3) . ?
C55 H55 0.93 . ?
C52 C53 1.379(3) . ?
C52 H52 0.93 . ?
C54 C53 1.381(3) . ?
C54 C8 1.503(3) . ?
C3 C2 1.386(3) . ?
C3 H3 0.93 . ?
C2 C21 1.498(3) . ?
C53 H53 0.93 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C71 F1 1.324(2) . ?
C71 F2 1.329(3) . ?
C71 F3 1.328(3) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?

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
C5 N4 C3A 118.71(14) . . ?
C56 C51 C52 117.45(16) . . ?
C56 C51 C5 120.62(15) . . ?
C52 C51 C5 121.92(15) . . ?
N4 C5 C6 121.31(15) . . ?
N4 C5 C51 118.73(14) . . ?
C6 C5 C51 119.96(15) . . ?
C7 N8 N1 127.00(15) . . ?
C7 N8 C3A 120.59(14) . . ?
N1 N8 C3A 112.41(14) . . ?
N4 C3A C3 133.60(16) . . ?
N4 C3A N8 121.24(15) . . ?
C3 C3A N8 105.16(14) . . ?
C6 C7 N8 118.34(16) . . ?
C6 C7 C71 123.33(17) . . ?
N8 C7 C71 118.34(16) . . ?
C2 N1 N8 103.37(14) . . ?
C7 C6 C5 119.80(16) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C55 C56 C51 120.88(17) . . ?
C55 C56 H56 119.6 . . ?
C51 C56 H56 119.6 . . ?
C56 C55 C54 121.77(17) . . ?
C56 C55 H55 119.1 . . ?
C54 C55 H55 119.1 . . ?
C53 C52 C51 121.14(17) . . ?
C53 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C53 C54 C55 117.21(16) . . ?
C53 C54 C8 121.85(18) . . ?
C55 C54 C8 120.94(18) . . ?
C3A C3 C2 106.09(15) . . ?
C3A C3 H3 127 . . ?
C2 C3 H3 127 . . ?
N1 C2 C3 112.96(15) . . ?
N1 C2 C21 117.85(17) . . ?
C3 C2 C21 129.19(17) . . ?
C52 C53 C54 121.54(17) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 H53 119.2 . . ?
C54 C8 H8A 109.5 . . ?
C54 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C54 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F1 C71 F2 107.10(17) . . ?
F1 C71 F3 106.78(19) . . ?
F2 C71 F3 107.23(18) . . ?
F1 C71 C7 110.93(17) . . ?
F2 C71 C7 112.3(2) . . ?
F3 C71 C7 112.23(18) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
N4 C51 C5 C56 -14.4(2) . . . . ?
N4 C51 C5 C52 166.94(16) . . . . ?

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p212121
_database_code_depnum_ccdc_archive 'CCDC 1056491'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2014-12-17T13:17:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'5-(4-chlorophenyl)-7-trifluoromethyl-2-methylpyrirazole[1,5-a]pyridine'
;
_chemical_name_common            
'chlorophenyl trifluoromethyl methylpyrirazole pyridine'
_chemical_formula_moiety         'C14 H9 Cl F3 N3'
_chemical_formula_sum            'C14 H9 Cl F3 N3'
_chemical_formula_weight         311.69
_chemical_melting_point          none
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  P2ac2ab
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'

_cell_length_a                   4.7929(4)
_cell_length_b                   10.5914(9)
_cell_length_c                   26.224(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1331.22(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4295
_cell_measurement_theta_min      2.4715
_cell_measurement_theta_max      22.3725

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.752
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.109
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_T_max  0.98976

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_number            20143
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.3
_diffrn_reflns_theta_full        27.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             2967
_reflns_number_gt                2128
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.1651P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl Cl -1.00790(15) 0.34926(6) 0.53173(2) 0.06332(19) Uani 1 1 d . . .
F2 F -0.0340(5) 0.96231(17) 0.76443(6) 0.0980(6) Uani 1 1 d . . .
F3 F 0.3028(4) 0.8324(2) 0.76468(6) 0.0983(6) Uani 1 1 d . . .
F1 F -0.1109(4) 0.76737(17) 0.77899(5) 0.0859(6) Uani 1 1 d . . .
N8 N 0.1417(4) 0.89499(16) 0.66208(7) 0.0462(5) Uani 1 1 d . . .
N4 N -0.0778(4) 0.79491(17) 0.59077(7) 0.0461(5) Uani 1 1 d . . .
N1 N 0.3289(5) 0.98692(18) 0.67342(7) 0.0547(5) Uani 1 1 d . . .
C51 C -0.4185(4) 0.63223(19) 0.60135(8) 0.0403(5) Uani 1 1 d . . .
C5 C -0.2184(5) 0.7238(2) 0.62317(8) 0.0411(5) Uani 1 1 d . . .
C3A C 0.1031(5) 0.8803(2) 0.60968(8) 0.0455(6) Uani 1 1 d . . .
C56 C -0.4806(6) 0.6352(2) 0.54936(7) 0.0481(5) Uani 1 1 d . . .
H56 H -0.3977 0.696 0.5288 0.058 Uiso 1 1 calc R . .
C6 C -0.1829(5) 0.7365(2) 0.67687(8) 0.0459(5) Uani 1 1 d . . .
H6 H -0.2834 0.6853 0.699 0.055 Uiso 1 1 calc R . .
C54 C -0.7851(5) 0.4596(2) 0.55858(8) 0.0461(6) Uani 1 1 d . . .
C2 C 0.4092(5) 1.0294(2) 0.62748(9) 0.0514(6) Uani 1 1 d . . .
C7 C -0.0043(5) 0.8227(2) 0.69541(7) 0.0465(5) Uani 1 1 d . . .
C3 C 0.2772(5) 0.9674(2) 0.58764(9) 0.0513(6) Uani 1 1 d . . .
H3 H 0.3018 0.982 0.553 0.062 Uiso 1 1 calc R . .
C52 C -0.5478(6) 0.5407(2) 0.63091(8) 0.0530(6) Uani 1 1 d . . .
H52 H -0.5101 0.537 0.6657 0.064 Uiso 1 1 calc R . .
C71 C 0.0385(6) 0.8464(3) 0.75109(9) 0.0653(7) Uani 1 1 d . . .
C53 C -0.7308(6) 0.4553(2) 0.60982(8) 0.0534(6) Uani 1 1 d . . .
H53 H -0.8171 0.3951 0.6302 0.064 Uiso 1 1 calc R . .
C55 C -0.6621(5) 0.5498(2) 0.52817(9) 0.0507(6) Uani 1 1 d . . .
H55 H -0.7018 0.5528 0.4935 0.061 Uiso 1 1 calc R . .
C21 C 0.6164(6) 1.1340(2) 0.62470(11) 0.0683(8) Uani 1 1 d . . .
H21A H 0.6712 1.1579 0.6586 0.103 Uiso 1 1 calc R . .
H21B H 0.5342 1.2052 0.6078 0.103 Uiso 1 1 calc R . .
H21C H 0.7773 1.1063 0.606 0.103 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
Cl C54 1.732(2) . ?
F2 C71 1.323(3) . ?
F3 C71 1.324(3) . ?
F1 C71 1.322(3) . ?
N8 C7 1.357(3) . ?
N8 N1 1.357(3) . ?
N8 C3A 1.395(3) . ?
N4 C5 1.321(3) . ?
N4 C3A 1.347(3) . ?
N1 C2 1.342(3) . ?
C51 C52 1.387(3) . ?
C51 C56 1.396(3) . ?
C51 C5 1.479(3) . ?
C5 C6 1.425(3) . ?
C3A C3 1.372(3) . ?
C56 C55 1.373(3) . ?
C6 C7 1.342(3) . ?
C54 C53 1.369(3) . ?
C54 C55 1.377(3) . ?
C2 C3 1.387(3) . ?
C2 C21 1.489(3) . ?
C7 C71 1.496(3) . ?
C52 C53 1.376(3) . ?

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
C7 N8 N1 127.22(19) . . ?
C7 N8 C3A 120.22(19) . . ?
N1 N8 C3A 112.55(18) . . ?
C5 N4 C3A 118.34(19) . . ?
C2 N1 N8 103.50(18) . . ?
C52 C51 C56 117.8(2) . . ?
C52 C51 C5 122.11(19) . . ?
C56 C51 C5 120.09(19) . . ?
N4 C5 C6 121.4(2) . . ?
N4 C5 C51 117.13(19) . . ?
C6 C5 C51 121.5(2) . . ?
N4 C3A C3 133.5(2) . . ?
N4 C3A N8 121.50(19) . . ?
C3 C3A N8 105.0(2) . . ?
C55 C56 C51 121.0(2) . . ?
C7 C6 C5 119.9(2) . . ?
C53 C54 C55 120.6(2) . . ?
C53 C54 Cl 119.58(18) . . ?
C55 C54 Cl 119.77(17) . . ?
N1 C2 C3 112.8(2) . . ?
N1 C2 C21 119.0(2) . . ?
C3 C2 C21 128.3(2) . . ?
C6 C7 N8 118.64(19) . . ?
C6 C7 C71 123.7(2) . . ?
N8 C7 C71 117.6(2) . . ?
C3A C3 C2 106.2(2) . . ?
C53 C52 C51 121.3(2) . . ?
F1 C71 F2 107.4(2) . . ?
F1 C71 F3 107.3(2) . . ?
F2 C71 F3 106.5(3) . . ?
F1 C71 C7 111.1(2) . . ?
F2 C71 C7 112.2(2) . . ?
F3 C71 C7 112.0(2) . . ?
C54 C53 C52 119.6(2) . . ?
C56 C55 C54 119.6(2) . . ?

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
C7 N8 N1 C2 -179.3(2) . . . . ?
C3A N8 N1 C2 -0.4(2) . . . . ?
C3A N4 C5 C6 0.4(3) . . . . ?
C3A N4 C5 C51 179.12(18) . . . . ?
C52 C51 C5 N4 170.6(2) . . . . ?
C56 C51 C5 N4 -8.7(3) . . . . ?
C52 C51 C5 C6 -10.6(3) . . . . ?
C56 C51 C5 C6 170.1(2) . . . . ?
C5 N4 C3A C3 -179.6(2) . . . . ?
C5 N4 C3A N8 -0.5(3) . . . . ?
C7 N8 C3A N4 0.0(3) . . . . ?
N1 N8 C3A N4 -179.02(19) . . . . ?
C7 N8 C3A C3 179.33(19) . . . . ?
N1 N8 C3A C3 0.3(2) . . . . ?
C52 C51 C56 C55 -0.4(3) . . . . ?
C5 C51 C56 C55 178.9(2) . . . . ?
N4 C5 C6 C7 0.3(3) . . . . ?
C51 C5 C6 C7 -178.4(2) . . . . ?
N8 N1 C2 C3 0.3(3) . . . . ?
N8 N1 C2 C21 179.4(2) . . . . ?
C5 C6 C7 N8 -0.8(3) . . . . ?
C5 C6 C7 C71 177.5(2) . . . . ?
N1 N8 C7 C6 179.5(2) . . . . ?
C3A N8 C7 C6 0.7(3) . . . . ?
N1 N8 C7 C71 1.1(3) . . . . ?
C3A N8 C7 C71 -177.7(2) . . . . ?
N4 C3A C3 C2 179.1(2) . . . . ?
N8 C3A C3 C2 -0.1(2) . . . . ?
N1 C2 C3 C3A -0.1(3) . . . . ?
C21 C2 C3 C3A -179.1(2) . . . . ?
C56 C51 C52 C53 0.1(4) . . . . ?
C5 C51 C52 C53 -179.2(2) . . . . ?
C6 C7 C71 F1 3.3(4) . . . . ?
N8 C7 C71 F1 -178.4(2) . . . . ?
C6 C7 C71 F2 -116.9(3) . . . . ?
N8 C7 C71 F2 61.3(3) . . . . ?
C6 C7 C71 F3 123.3(3) . . . . ?
N8 C7 C71 F3 -58.4(3) . . . . ?
C55 C54 C53 C52 -1.1(4) . . . . ?
Cl C54 C53 C52 178.19(19) . . . . ?
C51 C52 C53 C54 0.6(4) . . . . ?
C51 C56 C55 C54 0.0(4) . . . . ?
C53 C54 C55 C56 0.8(4) . . . . ?
Cl C54 C55 C56 -178.48(18) . . . . ?

# END of CIF
