#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221793.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_2221793
loop_
_publ_author_name
'Yao, Ji-Yuan'
'Xiao, Jie'
'Zhao, Hong'
_publ_section_title
;
 Dimethyl 1-(2-cyanobenzyl)-1H-pyrazole-3,5-dicarboxylate
;
_journal_coeditor_code           RZ2312
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1158
_journal_paper_doi               10.1107/S1600536809015153
_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-(2-cyanobenzyl)-1H-pyrazole-3,5-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.670(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2416(19)
_cell_length_b                   10.977(3)
_cell_length_c                   18.405(4)
_cell_measurement_reflns_used    3210
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.92
_cell_volume                     1437.7(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14431
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0522
_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)+(0.0618P)²+0.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                2452
_reflns_number_total             3287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2312.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221793
_cod_database_fobs_code          2221793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_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
C C1 0.7452(2) -0.11741(14) -0.00030(8) 0.0384(4) Uani d . 1 . .
C C2 0.7207(2) 0.00398(14) -0.02209(9) 0.0384(4) Uani d . 1 . .
H H2 0.6593 0.0337 -0.0675 0.046 Uiso calc R 1 . .
C C3 0.8066(2) 0.07034(14) 0.03796(9) 0.0369(4) Uani d . 1 . .
C C4 0.6825(2) -0.22943(15) -0.04182(9) 0.0430(4) Uani d . 1 . .
C C5 0.5284(3) -0.3033(2) -0.15741(12) 0.0698(6) Uani d . 1 . .
H H5A 0.6333 -0.3544 -0.1618 0.105 Uiso calc R 1 . .
H H5B 0.4715 -0.2736 -0.2054 0.105 Uiso calc R 1 . .
H H5C 0.4378 -0.3494 -0.1368 0.105 Uiso calc R 1 . .
C C6 0.8293(2) 0.20236(15) 0.04805(9) 0.0419(4) Uani d . 1 . .
C C7 0.7579(3) 0.39182(17) -0.01060(12) 0.0691(6) Uani d . 1 . .
H H7A 0.6940 0.4259 0.0259 0.104 Uiso calc R 1 . .
H H7B 0.7038 0.4234 -0.0584 0.104 Uiso calc R 1 . .
H H7C 0.8886 0.4132 0.0009 0.104 Uiso calc R 1 . .
C C8 0.9833(2) 0.00848(16) 0.16631(9) 0.0438(4) Uani d . 1 . .
H H8A 1.0696 0.0758 0.1655 0.053 Uiso calc R 1 . .
H H8B 1.0572 -0.0635 0.1826 0.053 Uiso calc R 1 . .
C C9 0.8571(2) 0.03652(14) 0.22102(9) 0.0409(4) Uani d . 1 . .
C C10 0.9142(2) 0.11795(15) 0.27911(9) 0.0455(4) Uani d . 1 . .
C C11 0.8042(3) 0.13819(17) 0.33260(10) 0.0572(5) Uani d . 1 . .
H H11 0.8447 0.1919 0.3714 0.069 Uiso calc R 1 . .
C C12 0.6365(3) 0.0788(2) 0.32785(11) 0.0639(5) Uani d . 1 . .
H H12 0.5623 0.0924 0.3633 0.077 Uiso calc R 1 . .
C C13 0.5775(3) -0.0008(2) 0.27081(12) 0.0636(5) Uani d . 1 . .
H H13 0.4631 -0.0408 0.2677 0.076 Uiso calc R 1 . .
C C14 0.6869(3) -0.02201(17) 0.21785(10) 0.0519(4) Uani d . 1 . .
H H14 0.6452 -0.0764 0.1796 0.062 Uiso calc R 1 . .
C C15 1.0869(3) 0.18543(18) 0.28545(10) 0.0560(5) Uani d . 1 . .
N N1 0.87843(18) -0.01204(12) 0.09157(7) 0.0385(3) Uani d . 1 . .
N N2 0.84141(19) -0.12686(12) 0.06921(7) 0.0414(3) Uani d . 1 . .
N N3 1.2207(3) 0.24250(19) 0.29236(11) 0.0811(6) Uani d . 1 . .
O O1 0.7088(2) -0.33067(12) -0.01849(7) 0.0649(4) Uani d . 1 . .
O O2 0.5924(2) -0.20179(11) -0.10967(7) 0.0574(4) Uani d . 1 . .
O O3 0.9169(2) 0.25110(12) 0.10214(7) 0.0645(4) Uani d . 1 . .
O O4 0.7390(2) 0.26063(10) -0.01091(7) 0.0568(4) Uani d . 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
N2 C1 C2 . . 111.35(14) ?
N2 C1 C4 . . 119.02(14) ?
C2 C1 C4 . . 129.63(15) ?
C3 C2 C1 . . 105.13(14) ?
C3 C2 H2 . . 127.4 ?
C1 C2 H2 . . 127.4 ?
N1 C3 C2 . . 106.57(13) ?
N1 C3 C6 . . 122.89(14) ?
C2 C3 C6 . . 130.53(15) ?
O1 C4 O2 . . 124.53(16) ?
O1 C4 C1 . . 125.21(16) ?
O2 C4 C1 . . 110.25(14) ?
O2 C5 H5A . . 109.5 ?
O2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
O2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
O3 C6 O4 . . 124.65(16) ?
O3 C6 C3 . . 125.05(16) ?
O4 C6 C3 . . 110.30(14) ?
O4 C7 H7A . . 109.5 ?
O4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 C9 . . 112.67(14) ?
N1 C8 H8A . . 109.1 ?
C9 C8 H8A . . 109.1 ?
N1 C8 H8B . . 109.1 ?
C9 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C14 C9 C10 . . 117.76(16) ?
C14 C9 C8 . . 121.46(15) ?
C10 C9 C8 . . 120.69(16) ?
C11 C10 C9 . . 121.04(18) ?
C11 C10 C15 . . 117.53(17) ?
C9 C10 C15 . . 121.42(16) ?
C12 C11 C10 . . 119.74(18) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 119.98(18) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C9 C14 C13 . . 120.93(18) ?
C9 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
N3 C15 C10 . . 177.0(2) ?
N2 N1 C3 . . 111.90(13) ?
N2 N1 C8 . . 118.35(13) ?
C3 N1 C8 . . 129.75(14) ?
N1 N2 C1 . . 105.04(12) ?
C4 O2 C5 . . 116.21(14) ?
C6 O4 C7 . . 116.47(14) ?
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
C1 N2 . 1.343(2) ?
C1 C2 . 1.393(2) ?
C1 C4 . 1.474(2) ?
C2 C3 . 1.373(2) ?
C2 H2 . 0.9300 ?
C3 N1 . 1.368(2) ?
C3 C6 . 1.466(2) ?
C4 O1 . 1.194(2) ?
C4 O2 . 1.332(2) ?
C5 O2 . 1.441(2) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 O3 . 1.202(2) ?
C6 O4 . 1.324(2) ?
C7 O4 . 1.446(2) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 N1 . 1.460(2) ?
C8 C9 . 1.512(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C14 . 1.381(3) ?
C9 C10 . 1.396(2) ?
C10 C11 . 1.394(3) ?
C10 C15 . 1.440(3) ?
C11 C12 . 1.367(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 N3 . 1.141(3) ?
N1 N2 . 1.3376(18) ?
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
C8 H8A O3 . 0.97 2.41 2.917(2) 112
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742245
