#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221658.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221658
loop_
_publ_author_name
'Xiao, Jie'
'Zhao, Hong'
_publ_section_title
;
 Dimethyl 1-(4-cyanobenzyl)-1H-pyrazole-3,5-dicarboxylate
;
_journal_coeditor_code           FB2152
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1175
_journal_paper_doi               10.1107/S1600536809015578
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 N3 O4'
_chemical_formula_moiety         'C15 H13 N3 O4'
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_weight         299.28
_chemical_name_systematic
;
Dimethyl 1-(4-cyanobenzyl)-1H-pyrazole-3,5-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.820(5)
_cell_angle_beta                 88.900(6)
_cell_angle_gamma                68.818(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4981(13)
_cell_length_b                   9.1753(9)
_cell_length_c                   12.2884(18)
_cell_measurement_reflns_used    1468
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.4333
_cell_measurement_theta_min      2.5544
_cell_volume                     734.51(19)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.5
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7543
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.152
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0703P)²+0.0489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                1972
_reflns_number_total             3330
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2152.cif
_cod_data_source_block           I
_cod_original_cell_volume        734.51(18)
_cod_database_code               2221658
_cod_database_fobs_code          2221658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5650(2) -0.3342(2) 0.04531(15) 0.0655(5) Uani d . 1 . .
O O2 0.5168(3) -0.3555(2) 0.22929(16) 0.0819(6) Uani d . 1 . .
O O3 0.0543(3) 0.2623(2) -0.24779(14) 0.0728(5) Uani d . 1 . .
O O4 -0.1136(3) 0.4051(2) -0.14182(15) 0.0793(6) Uani d . 1 . .
N N1 0.2237(2) -0.0155(2) 0.13109(15) 0.0491(5) Uani d . 1 . .
N N2 0.0980(2) 0.1342(2) 0.06034(16) 0.0503(5) Uani d . 1 . .
N N3 0.8678(4) 0.2304(3) 0.4352(3) 0.0966(9) Uani d . 1 . .
C C1 0.3321(3) -0.1079(3) 0.06994(19) 0.0468(5) Uani d . 1 . .
C C2 0.2698(3) -0.0139(3) -0.04608(18) 0.0479(5) Uani d . 1 . .
H H2 0.3143 -0.0430 -0.1098 0.057 Uiso calc R 1 . .
C C3 0.1264(3) 0.1341(3) -0.04801(19) 0.0472(5) Uani d . 1 . .
C C4 0.4791(3) -0.2778(3) 0.1258(2) 0.0530(6) Uani d . 1 . .
C C5 0.0081(3) 0.2824(3) -0.1475(2) 0.0515(6) Uani d . 1 . .
C C6 0.2365(3) -0.0489(3) 0.25677(19) 0.0550(6) Uani d . 1 . .
H H6A 0.2761 -0.1686 0.2991 0.066 Uiso calc R 1 . .
H H6B 0.1102 0.0062 0.2765 0.066 Uiso calc R 1 . .
C C7 0.3779(3) 0.0122(3) 0.29447(18) 0.0479(5) Uani d . 1 . .
C C8 0.3384(3) 0.1819(3) 0.2585(2) 0.0576(6) Uani d . 1 . .
H H8 0.2252 0.2581 0.2104 0.069 Uiso calc R 1 . .
C C9 0.4644(3) 0.2392(3) 0.2932(2) 0.0581(6) Uani d . 1 . .
H H9 0.4368 0.3538 0.2687 0.070 Uiso calc R 1 . .
C C10 0.6333(3) 0.1255(3) 0.36490(19) 0.0529(6) Uani d . 1 . .
C C11 0.6731(3) -0.0434(3) 0.4016(2) 0.0588(6) Uani d . 1 . .
H H11 0.7857 -0.1197 0.4504 0.071 Uiso calc R 1 . .
C C12 0.5455(3) -0.1000(3) 0.36587(19) 0.0548(6) Uani d . 1 . .
H H12 0.5731 -0.2146 0.3902 0.066 Uiso calc R 1 . .
C C13 0.7641(4) 0.1848(3) 0.4034(2) 0.0678(7) Uani d . 1 . .
C C14 0.7145(4) -0.5000(3) 0.0858(3) 0.0785(8) Uani d . 1 . .
H H14A 0.7910 -0.5143 0.0239 0.118 Uiso calc PR 0.50 . .
H H14B 0.6569 -0.5824 0.1090 0.118 Uiso calc PR 0.50 . .
H H14C 0.7949 -0.5136 0.1512 0.118 Uiso calc PR 0.50 . .
H H14D 0.7042 -0.5592 0.1655 0.118 Uiso calc PR 0.50 . .
H H14E 0.8383 -0.4911 0.0804 0.118 Uiso calc PR 0.50 . .
H H14F 0.7003 -0.5600 0.0382 0.118 Uiso calc PR 0.50 . .
C C15 -0.0426(5) 0.4051(3) -0.3519(2) 0.0935(10) Uani d . 1 . .
H H15A -0.1784 0.4472 -0.3465 0.140 Uiso calc R 1 . .
H H15B -0.0203 0.3722 -0.4187 0.140 Uiso calc R 1 . .
H H15C 0.0063 0.4912 -0.3600 0.140 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C14 . . 117.1(2) ?
C5 O3 C15 . . 115.7(2) ?
N2 N1 C1 . . 112.02(17) ?
N2 N1 C6 . . 117.49(18) ?
C1 N1 C6 . . 130.25(19) ?
N1 N2 C3 . . 104.47(18) ?
N1 C1 C2 . . 106.61(19) ?
N1 C1 C4 . . 123.3(2) ?
C2 C1 C4 . . 130.0(2) ?
C1 C2 C3 . . 105.17(19) ?
C1 C2 H2 . . 127.4 ?
C3 C2 H2 . . 127.4 ?
N2 C3 C2 . . 111.72(19) ?
N2 C3 C5 . . 118.3(2) ?
C2 C3 C5 . . 130.0(2) ?
O2 C4 O1 . . 124.4(2) ?
O2 C4 C1 . . 125.6(2) ?
O1 C4 C1 . . 110.0(2) ?
O4 C5 O3 . . 123.3(2) ?
O4 C5 C3 . . 126.0(2) ?
O3 C5 C3 . . 110.7(2) ?
N1 C6 C7 . . 112.00(17) ?
N1 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
N1 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C12 C7 C8 . . 119.4(2) ?
C12 C7 C6 . . 120.5(2) ?
C8 C7 C6 . . 120.0(2) ?
C9 C8 C7 . . 120.6(2) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 119.6(2) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C11 C10 C9 . . 120.1(2) ?
C11 C10 C13 . . 120.0(2) ?
C9 C10 C13 . . 119.9(2) ?
C10 C11 C12 . . 119.9(2) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C7 C12 C11 . . 120.3(2) ?
C7 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
N3 C13 C10 . . 179.2(3) ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O1 C14 H14D . . 109.5 ?
H14A C14 H14D . . 141.1 ?
H14B C14 H14D . . 56.3 ?
H14C C14 H14D . . 56.3 ?
O1 C14 H14E . . 109.5 ?
H14A C14 H14E . . 56.3 ?
H14B C14 H14E . . 141.1 ?
H14C C14 H14E . . 56.3 ?
H14D C14 H14E . . 109.5 ?
O1 C14 H14F . . 109.5 ?
H14A C14 H14F . . 56.3 ?
H14B C14 H14F . . 56.3 ?
H14C C14 H14F . . 141.1 ?
H14D C14 H14F . . 109.5 ?
H14E C14 H14F . . 109.5 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C4 . 1.323(3) ?
O1 C14 . 1.445(3) ?
O2 C4 . 1.203(3) ?
O3 C5 . 1.330(3) ?
O3 C15 . 1.440(3) ?
O4 C5 . 1.189(3) ?
N1 N2 . 1.343(2) ?
N1 C1 . 1.364(3) ?
N1 C6 . 1.465(3) ?
N2 C3 . 1.345(3) ?
N3 C13 . 1.136(3) ?
C1 C2 . 1.371(3) ?
C1 C4 . 1.471(3) ?
C2 C3 . 1.387(3) ?
C2 H2 . 0.9300 ?
C3 C5 . 1.468(3) ?
C6 C7 . 1.510(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C12 . 1.376(3) ?
C7 C8 . 1.380(3) ?
C8 C9 . 1.371(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.386(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.373(3) ?
C10 C13 . 1.436(3) ?
C11 C12 . 1.382(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C14 H14D . 0.9600 ?
C14 H14E . 0.9600 ?
C14 H14F . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6A O2 . 0.97 2.38 2.966(3) 118.6
C14 H14A O4 1_645 0.96 2.41 3.312(4) 156.4
C2 H2 Cg2 2_655 0.93 3.04 3.952(3) 166.01
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
C1 N1 N2 C3 . . . . 1.0(2) ?
C6 N1 N2 C3 . . . . 175.97(16) ?
N2 N1 C1 C2 . . . . -1.3(2) ?
C6 N1 C1 C2 . . . . -175.37(19) ?
N2 N1 C1 C4 . . . . -179.11(18) ?
C6 N1 C1 C4 . . . . 6.8(3) ?
N1 C1 C2 C3 . . . . 0.9(2) ?
C4 C1 C2 C3 . . . . 178.6(2) ?
N1 N2 C3 C2 . . . . -0.4(2) ?
N1 N2 C3 C5 . . . . 179.58(17) ?
C1 C2 C3 N2 . . . . -0.3(2) ?
C1 C2 C3 C5 . . . . 179.7(2) ?
C14 O1 C4 O2 . . . . -0.4(3) ?
C14 O1 C4 C1 . . . . 179.79(19) ?
N1 C1 C4 O2 . . . . 2.2(4) ?
C2 C1 C4 O2 . . . . -175.2(2) ?
N1 C1 C4 O1 . . . . -177.99(18) ?
C2 C1 C4 O1 . . . . 4.7(3) ?
C15 O3 C5 O4 . . . . 4.7(4) ?
C15 O3 C5 C3 . . . . -175.6(2) ?
N2 C3 C5 O4 . . . . -0.4(3) ?
C2 C3 C5 O4 . . . . 179.6(2) ?
N2 C3 C5 O3 . . . . 179.86(18) ?
C2 C3 C5 O3 . . . . -0.1(3) ?
N2 N1 C6 C7 . . . . -87.3(2) ?
C1 N1 C6 C7 . . . . 86.6(3) ?
N1 C6 C7 C12 . . . . -113.0(2) ?
N1 C6 C7 C8 . . . . 67.8(3) ?
C12 C7 C8 C9 . . . . 0.1(4) ?
C6 C7 C8 C9 . . . . 179.2(2) ?
C7 C8 C9 C10 . . . . 0.1(4) ?
C8 C9 C10 C11 . . . . -0.5(4) ?
C8 C9 C10 C13 . . . . -178.8(2) ?
C9 C10 C11 C12 . . . . 0.7(4) ?
C13 C10 C11 C12 . . . . 179.0(2) ?
C8 C7 C12 C11 . . . . 0.2(3) ?
C6 C7 C12 C11 . . . . -179.0(2) ?
C10 C11 C12 C7 . . . . -0.6(4) ?
