##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 1-benzyl-3-(4-methylphenyl)-1H-pyrazole-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H20 N2 O2'
_chemical_formula_sum     'C20 H20 N2 O2'
_chemical_formula_iupac     'C20 H20 N2 O2'
_chemical_formula_weight     320.38
_chemical_melting_point     ?
_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     7.666(4)
_cell_length_b     10.160(6)
_cell_length_c     11.381(7)
_cell_angle_alpha     83.991(9)
_cell_angle_beta     87.466(9)
_cell_angle_gamma     85.470(10)
_cell_volume     878.2(9)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1778
_cell_measurement_theta_min     2.57
_cell_measurement_theta_max     24.18
_cell_measurement_temperature     298(2)
_exptl_crystal_description     BLOCK
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.212
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     340
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.9836
_exptl_absorpt_correction_T_max     0.9906
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4489
_diffrn_reflns_av_R_equivalents     0.0323
_diffrn_reflns_av_sigmaI/netI     0.0460
_diffrn_reflns_theta_min     1.80
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     3045
_reflns_number_gt     2182
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0864
_refine_ls_R_factor_gt     0.0661
_refine_ls_wR_factor_gt     0.1967
_refine_ls_wR_factor_ref     0.2201
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     3045
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1348P)²+0.1525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.342
_refine_diff_density_min     -0.213
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.3059(3) 0.5585(2) 0.70282(17) 0.0826(7) Uani d . 1 . .
    O O2 0.2483(3) 0.6693(2) 0.86211(17) 0.0703(6) Uani d . 1 . .
    N N1 0.3539(3) 0.3185(2) 0.86746(18) 0.0548(6) Uani d . 1 . .
    N N2 0.3537(3) 0.2290(2) 0.96361(19) 0.0569(6) Uani d . 1 . .
    C C1 0.1960(6) 0.9004(4) 0.8654(3) 0.0955(11) Uani d . 1 . .
    H H1A 0.1004 0.8824 0.9206 0.143 Uiso calc R 1 . .
    H H1B 0.1698 0.9836 0.8191 0.143 Uiso calc R 1 . .
    H H1C 0.3006 0.9049 0.9077 0.143 Uiso calc R 1 . .
    C C2 0.2227(5) 0.7932(3) 0.7865(3) 0.0764(9) Uani d . 1 . .
    H H2A 0.1213 0.7919 0.7387 0.092 Uiso calc R 1 . .
    H H2B 0.3246 0.8065 0.7342 0.092 Uiso calc R 1 . .
    C C3 0.2870(3) 0.5601(3) 0.8081(2) 0.0597(7) Uani d . 1 . .
    C C4 0.3021(3) 0.4439(3) 0.8954(2) 0.0528(6) Uani d . 1 . .
    C C5 0.2658(3) 0.4323(3) 1.0152(2) 0.0551(7) Uani d . 1 . .
    H H5 0.2268 0.5002 1.0609 0.066 Uiso calc R 1 . .
    C C6 0.2990(3) 0.2986(3) 1.0543(2) 0.0517(6) Uani d . 1 . .
    C C7 0.2828(3) 0.2321(3) 1.1751(2) 0.0523(6) Uani d . 1 . .
    C C8 0.2692(4) 0.3059(3) 1.2712(2) 0.0625(7) Uani d . 1 . .
    H H8 0.2707 0.3978 1.2586 0.075 Uiso calc R 1 . .
    C C9 0.2535(4) 0.2459(3) 1.3851(2) 0.0669(8) Uani d . 1 . .
    H H9 0.2442 0.2982 1.4478 0.080 Uiso calc R 1 . .
    C C10 0.2512(4) 0.1096(3) 1.4083(2) 0.0616(7) Uani d . 1 . .
    C C11 0.2643(4) 0.0367(3) 1.3121(3) 0.0717(8) Uani d . 1 . .
    H H11 0.2620 -0.0551 1.3247 0.086 Uiso calc R 1 . .
    C C12 0.2806(4) 0.0958(3) 1.1980(2) 0.0648(8) Uani d . 1 . .
    H H12 0.2903 0.0433 1.1355 0.078 Uiso calc R 1 . .
    C C13 0.2361(5) 0.0423(4) 1.5327(3) 0.0880(10) Uani d . 1 . .
    H H13A 0.2140 -0.0490 1.5301 0.132 Uiso calc R 1 . .
    H H13B 0.1414 0.0861 1.5752 0.132 Uiso calc R 1 . .
    H H13C 0.3434 0.0471 1.5719 0.132 Uiso calc R 1 . .
    C C14 0.4189(3) 0.2742(3) 0.7545(2) 0.0608(7) Uani d . 1 . .
    H H14A 0.3443 0.3163 0.6925 0.073 Uiso calc R 1 . .
    H H14B 0.4110 0.1791 0.7574 0.073 Uiso calc R 1 . .
    C C15 0.6048(3) 0.3050(2) 0.7234(2) 0.0485(6) Uani d . 1 . .
    C C16 0.6535(4) 0.3469(3) 0.6073(2) 0.0596(7) Uani d . 1 . .
    H H16 0.5692 0.3606 0.5501 0.071 Uiso calc R 1 . .
    C C17 0.8246(4) 0.3682(3) 0.5762(3) 0.0730(9) Uani d . 1 . .
    H H17 0.8563 0.3945 0.4979 0.088 Uiso calc R 1 . .
    C C18 0.9483(4) 0.3509(4) 0.6601(3) 0.0766(9) Uani d . 1 . .
    H H18 1.0637 0.3675 0.6390 0.092 Uiso calc R 1 . .
    C C19 0.9039(4) 0.3090(3) 0.7758(3) 0.0692(8) Uani d . 1 . .
    H H19 0.9892 0.2966 0.8324 0.083 Uiso calc R 1 . .
    C C20 0.7326(3) 0.2855(3) 0.8074(2) 0.0555(7) Uani d . 1 . .
    H H20 0.7025 0.2566 0.8853 0.067 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C3 . 1.202(3) ?
    O2 C3 . 1.332(3) ?
    O2 C2 . 1.453(3) ?
    N1 N2 . 1.348(3) ?
    N1 C4 . 1.369(3) ?
    N1 C14 . 1.461(3) ?
    N2 C6 . 1.345(3) ?
    C1 C2 . 1.480(5) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.463(4) ?
    C4 C5 . 1.374(3) ?
    C5 C6 . 1.392(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.471(4) ?
    C7 C12 . 1.384(4) ?
    C7 C8 . 1.386(4) ?
    C8 C9 . 1.378(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.384(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.381(4) ?
    C10 C13 . 1.510(4) ?
    C11 C12 . 1.376(4) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C15 . 1.502(3) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C20 . 1.388(4) ?
    C15 C16 . 1.389(4) ?
    C16 C17 . 1.372(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.364(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.377(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.379(4) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 O2 C2 . . 116.6(2) ?
    N2 N1 C4 . . 111.8(2) ?
    N2 N1 C14 . . 118.5(2) ?
    C4 N1 C14 . . 129.5(2) ?
    C6 N2 N1 . . 105.3(2) ?
    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 ?
    O2 C2 C1 . . 106.8(3) ?
    O2 C2 H2A . . 110.4 ?
    C1 C2 H2A . . 110.4 ?
    O2 C2 H2B . . 110.4 ?
    C1 C2 H2B . . 110.4 ?
    H2A C2 H2B . . 108.6 ?
    O1 C3 O2 . . 124.5(3) ?
    O1 C3 C4 . . 125.5(3) ?
    O2 C3 C4 . . 110.0(2) ?
    N1 C4 C5 . . 106.1(2) ?
    N1 C4 C3 . . 123.6(2) ?
    C5 C4 C3 . . 130.3(3) ?
    C4 C5 C6 . . 106.2(2) ?
    C4 C5 H5 . . 126.9 ?
    C6 C5 H5 . . 126.9 ?
    N2 C6 C5 . . 110.6(2) ?
    N2 C6 C7 . . 120.6(2) ?
    C5 C6 C7 . . 128.8(2) ?
    C12 C7 C8 . . 117.3(2) ?
    C12 C7 C6 . . 122.4(2) ?
    C8 C7 C6 . . 120.2(2) ?
    C9 C8 C7 . . 121.3(3) ?
    C9 C8 H8 . . 119.4 ?
    C7 C8 H8 . . 119.4 ?
    C8 C9 C10 . . 121.5(3) ?
    C8 C9 H9 . . 119.3 ?
    C10 C9 H9 . . 119.3 ?
    C11 C10 C9 . . 116.9(3) ?
    C11 C10 C13 . . 121.0(3) ?
    C9 C10 C13 . . 122.1(3) ?
    C12 C11 C10 . . 122.0(3) ?
    C12 C11 H11 . . 119.0 ?
    C10 C11 H11 . . 119.0 ?
    C11 C12 C7 . . 121.0(3) ?
    C11 C12 H12 . . 119.5 ?
    C7 C12 H12 . . 119.5 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N1 C14 C15 . . 113.41(19) ?
    N1 C14 H14A . . 108.9 ?
    C15 C14 H14A . . 108.9 ?
    N1 C14 H14B . . 108.9 ?
    C15 C14 H14B . . 108.9 ?
    H14A C14 H14B . . 107.7 ?
    C20 C15 C16 . . 118.7(2) ?
    C20 C15 C14 . . 121.2(2) ?
    C16 C15 C14 . . 119.9(2) ?
    C17 C16 C15 . . 120.7(2) ?
    C17 C16 H16 . . 119.7 ?
    C15 C16 H16 . . 119.7 ?
    C18 C17 C16 . . 119.9(3) ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C17 C18 C19 . . 120.6(3) ?
    C17 C18 H18 . . 119.7 ?
    C19 C18 H18 . . 119.7 ?
    C18 C19 C20 . . 119.7(3) ?
    C18 C19 H19 . . 120.1 ?
    C20 C19 H19 . . 120.1 ?
    C19 C20 C15 . . 120.3(2) ?
    C19 C20 H20 . . 119.9 ?
    C15 C20 H20 . . 119.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 N1 N2 C6 . . . . 0.6(3) ?
    C14 N1 N2 C6 . . . . 176.1(2) ?
    C3 O2 C2 C1 . . . . -175.4(3) ?
    C2 O2 C3 O1 . . . . 1.8(4) ?
    C2 O2 C3 C4 . . . . -177.9(2) ?
    N2 N1 C4 C5 . . . . -0.6(3) ?
    C14 N1 C4 C5 . . . . -175.4(2) ?
    N2 N1 C4 C3 . . . . -178.8(2) ?
    C14 N1 C4 C3 . . . . 6.4(4) ?
    O1 C3 C4 N1 . . . . 5.4(4) ?
    O2 C3 C4 N1 . . . . -174.9(2) ?
    O1 C3 C4 C5 . . . . -172.3(3) ?
    O2 C3 C4 C5 . . . . 7.4(4) ?
    N1 C4 C5 C6 . . . . 0.4(3) ?
    C3 C4 C5 C6 . . . . 178.4(2) ?
    N1 N2 C6 C5 . . . . -0.4(3) ?
    N1 N2 C6 C7 . . . . -179.9(2) ?
    C4 C5 C6 N2 . . . . 0.0(3) ?
    C4 C5 C6 C7 . . . . 179.5(2) ?
    N2 C6 C7 C12 . . . . -16.0(4) ?
    C5 C6 C7 C12 . . . . 164.6(3) ?
    N2 C6 C7 C8 . . . . 164.0(2) ?
    C5 C6 C7 C8 . . . . -15.4(4) ?
    C12 C7 C8 C9 . . . . -0.2(4) ?
    C6 C7 C8 C9 . . . . 179.8(2) ?
    C7 C8 C9 C10 . . . . 0.2(5) ?
    C8 C9 C10 C11 . . . . -0.4(5) ?
    C8 C9 C10 C13 . . . . 179.3(3) ?
    C9 C10 C11 C12 . . . . 0.6(5) ?
    C13 C10 C11 C12 . . . . -179.1(3) ?
    C10 C11 C12 C7 . . . . -0.7(5) ?
    C8 C7 C12 C11 . . . . 0.4(4) ?
    C6 C7 C12 C11 . . . . -179.6(3) ?
    N2 N1 C14 C15 . . . . -99.0(3) ?
    C4 N1 C14 C15 . . . . 75.5(3) ?
    N1 C14 C15 C20 . . . . 42.9(4) ?
    N1 C14 C15 C16 . . . . -140.7(3) ?
    C20 C15 C16 C17 . . . . 0.2(4) ?
    C14 C15 C16 C17 . . . . -176.3(3) ?
    C15 C16 C17 C18 . . . . -1.3(5) ?
    C16 C17 C18 C19 . . . . 1.5(5) ?
    C17 C18 C19 C20 . . . . -0.6(5) ?
    C18 C19 C20 C15 . . . . -0.5(4) ?
    C16 C15 C20 C19 . . . . 0.7(4) ?
    C14 C15 C20 C19 . . . . 177.2(2) ?
data_global
_journal_date_recd_electronic     2011-01-10
_journal_date_accepted     2011-01-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o468
_journal_page_last     o468
_journal_paper_category     QO
_journal_coeditor_code     JH2257
_publ_contact_author_name     'Yu-Liang Xiao'
_publ_contact_author_address
;
Taishan Medical College, Tai an, 271016,
;
_publ_contact_author_email     yqge@yahoo.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Ethyl 1-benzyl-3-(4-methylphenyl)-1H-pyrazole-5-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li, Yu-Qin' .
;
Taishan Medical College, Tai an 271016,
People's Republic of China
;
    'Jia, Bao-Xiu' .
;
Taishan Medical College, Tai an 271016,
People's Republic of China
;
    'Xiao, Yu-Liang' .
;
Taishan Medical College, Tai an 271016,
People's Republic of China
;
    'Guo, Feng-Guang' .
;
Taishan Medical College, Tai an 271016,
People's Republic of China
;
