# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_cm152m
_audit_block_doi                 10.5517/cc13rbt0
_database_code_depnum_ccdc_archive 'CCDC 1035332'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'ethyl 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C16H14N2O2
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8783(5)
_cell_length_b                   11.1617(14)
_cell_length_c                   15.3358(19)
_cell_angle_alpha                78.727(2)
_cell_angle_beta                 85.961(2)
_cell_angle_gamma                86.336(2)
_cell_volume                     648.58(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2752
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      28.05

_exptl_crystal_description       PLATES
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5041
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2527
_reflns_number_gt                2350
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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)+(0.0191P)²+0.5609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2527
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O2 O 1.1625(4) 0.34565(12) 0.64456(8) 0.0234(3) Uani 1 1 d . . .
O1 O 1.2316(4) 0.54823(13) 0.61751(9) 0.0291(4) Uani 1 1 d . . .
N2 N 0.6586(4) 0.39580(14) 0.88331(10) 0.0198(4) Uani 1 1 d . . .
N1 N 0.6941(4) 0.51783(15) 0.87684(10) 0.0216(4) Uani 1 1 d . . .
C14 C 1.1192(5) 0.45810(18) 0.66493(12) 0.0208(4) Uani 1 1 d . . .
C8 C 0.4981(5) 0.32420(19) 0.95555(13) 0.0243(4) Uani 1 1 d . . .
H8 H 0.4092 0.3573 1.0041 0.029 Uiso 1 1 calc R . .
C15 C 1.3556(5) 0.34114(19) 0.55991(12) 0.0246(4) Uani 1 1 d . . .
H15A H 1.5690 0.3831 0.5565 0.029 Uiso 1 1 calc R . .
H15B H 1.2194 0.3808 0.5107 0.029 Uiso 1 1 calc R . .
C11 C 0.7663(5) 0.22732(18) 0.80888(13) 0.0233(4) Uani 1 1 d . . .
H11 H 0.8552 0.1943 0.7603 0.028 Uiso 1 1 calc R . .
C7 C 0.8527(5) 0.55387(17) 0.79652(12) 0.0197(4) Uani 1 1 d . . .
C10 C 0.6082(5) 0.15510(19) 0.88036(14) 0.0271(5) Uani 1 1 d . . .
H10 H 0.5894 0.0724 0.8804 0.033 Uiso 1 1 calc R . .
C12 C 0.7946(5) 0.35305(18) 0.80897(12) 0.0194(4) Uani 1 1 d . . .
C13 C 0.9265(5) 0.45550(17) 0.75106(12) 0.0197(4) Uani 1 1 d . . .
C5 C 0.8428(5) 0.75109(19) 0.68539(14) 0.0271(5) Uani 1 1 d . . .
H5 H 0.7532 0.7118 0.6445 0.032 Uiso 1 1 calc R . .
C1 C 1.0505(5) 0.74597(19) 0.83018(14) 0.0246(4) Uani 1 1 d . . .
H1 H 1.1007 0.7029 0.8865 0.030 Uiso 1 1 calc R . .
C6 C 0.9212(5) 0.68535(17) 0.76915(13) 0.0212(4) Uani 1 1 d . . .
C9 C 0.4718(5) 0.20442(19) 0.95476(13) 0.0266(5) Uani 1 1 d . . .
H9 H 0.3640 0.1541 1.0032 0.032 Uiso 1 1 calc R . .
C2 C 1.1046(6) 0.8699(2) 0.80747(15) 0.0318(5) Uani 1 1 d . . .
H2 H 1.1904 0.9100 0.8485 0.038 Uiso 1 1 calc R . .
C16 C 1.4337(6) 0.2090(2) 0.55514(14) 0.0307(5) Uani 1 1 d . . .
H16A H 1.5597 0.1697 0.6055 0.046 Uiso 1 1 calc R . .
H16B H 1.5704 0.2034 0.5013 0.046 Uiso 1 1 calc R . .
H16C H 1.2209 0.1693 0.5556 0.046 Uiso 1 1 calc R . .
C3 C 1.0308(6) 0.9341(2) 0.72364(16) 0.0347(5) Uani 1 1 d . . .
H3 H 1.0703 1.0171 0.7080 0.042 Uiso 1 1 calc R . .
C4 C 0.8983(6) 0.8749(2) 0.66310(15) 0.0327(5) Uani 1 1 d . . .
H4 H 0.8461 0.9186 0.6071 0.039 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0273(8) 0.0262(7) 0.0167(7) -0.0059(6) 0.0042(6) -0.0010(6)
O1 0.0365(9) 0.0268(8) 0.0222(7) -0.0029(6) 0.0088(6) -0.0038(6)
N2 0.0212(8) 0.0219(8) 0.0165(8) -0.0041(6) -0.0015(6) -0.0013(7)
N1 0.0243(9) 0.0216(8) 0.0193(8) -0.0058(7) 0.0001(7) -0.0003(7)
C14 0.0188(10) 0.0258(10) 0.0175(9) -0.0035(8) -0.0038(8) 0.0013(8)
C8 0.0239(10) 0.0324(11) 0.0159(9) -0.0041(8) 0.0027(8) -0.0012(8)
C15 0.0250(11) 0.0332(11) 0.0151(9) -0.0062(8) 0.0033(8) 0.0012(8)
C11 0.0243(11) 0.0252(10) 0.0216(10) -0.0080(8) -0.0008(8) 0.0002(8)
C7 0.0188(10) 0.0244(10) 0.0161(9) -0.0046(8) -0.0014(7) 0.0003(8)
C10 0.0289(11) 0.0229(10) 0.0296(11) -0.0035(9) -0.0037(9) -0.0045(9)
C12 0.0164(9) 0.0257(10) 0.0163(9) -0.0051(8) -0.0026(7) 0.0019(7)
C13 0.0186(9) 0.0214(10) 0.0196(9) -0.0052(8) -0.0019(7) 0.0007(7)
C5 0.0295(11) 0.0262(11) 0.0255(11) -0.0067(8) -0.0002(9) 0.0021(9)
C1 0.0220(10) 0.0291(11) 0.0232(10) -0.0072(8) 0.0016(8) -0.0009(8)
C6 0.0186(10) 0.0226(10) 0.0227(10) -0.0069(8) 0.0031(8) 0.0005(8)
C9 0.0272(11) 0.0268(11) 0.0233(10) 0.0014(8) 0.0015(8) -0.0040(8)
C2 0.0276(12) 0.0302(12) 0.0406(13) -0.0158(10) 0.0053(10) -0.0056(9)
C16 0.0323(12) 0.0357(12) 0.0251(11) -0.0104(9) 0.0021(9) 0.0020(9)
C3 0.0382(13) 0.0202(11) 0.0439(14) -0.0067(10) 0.0121(11) -0.0025(9)
C4 0.0394(13) 0.0279(12) 0.0268(11) -0.0005(9) 0.0055(10) 0.0057(10)

_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
O2 C14 1.349(2) . ?
O2 C15 1.460(2) . ?
O1 C14 1.207(2) . ?
N2 N1 1.361(2) . ?
N2 C8 1.369(2) . ?
N2 C12 1.379(2) . ?
N1 C7 1.337(2) . ?
C14 C13 1.467(3) . ?
C8 C9 1.350(3) . ?
C8 H8 0.9300 . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 C10 1.360(3) . ?
C11 C12 1.415(3) . ?
C11 H11 0.9300 . ?
C7 C13 1.416(3) . ?
C7 C6 1.481(3) . ?
C10 C9 1.417(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.404(3) . ?
C5 C4 1.384(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C1 C2 1.385(3) . ?
C1 C6 1.394(3) . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
C14 O2 C15 114.71(15) . . ?
N1 N2 C8 123.18(16) . . ?
N1 N2 C12 112.93(15) . . ?
C8 N2 C12 123.88(17) . . ?
C7 N1 N2 104.63(15) . . ?
O1 C14 O2 123.04(17) . . ?
O1 C14 C13 125.24(18) . . ?
O2 C14 C13 111.71(16) . . ?
C9 C8 N2 118.51(18) . . ?
C9 C8 H8 120.7 . . ?
N2 C8 H8 120.7 . . ?
O2 C15 C16 107.73(16) . . ?
O2 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C10 C11 C12 119.53(18) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N1 C7 C13 112.08(17) . . ?
N1 C7 C6 117.27(16) . . ?
C13 C7 C6 130.64(17) . . ?
C11 C10 C9 120.73(19) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C12 C13 105.39(16) . . ?
N2 C12 C11 117.17(17) . . ?
C13 C12 C11 137.44(18) . . ?
C12 C13 C7 104.96(16) . . ?
C12 C13 C14 127.33(17) . . ?
C7 C13 C14 127.59(17) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C5 C6 C1 119.28(19) . . ?
C5 C6 C7 121.42(18) . . ?
C1 C6 C7 119.21(18) . . ?
C8 C9 C10 120.18(19) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane-Ethyl acetate'
_chemical_compound_source        Synthesis
