#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227309.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227309
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Chandrakantha, B.'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 Ethyl 1-tert-butyl-5-phenyl-1H-pyrazole-4-carboxylate
;
_journal_coeditor_code           CI5147
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2228
_journal_paper_doi               10.1107/S1600536810030643
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H20 N2 O2'
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_name_systematic
;
Ethyl 1-tert-butyl-5-phenyl-1H-pyrazole-4-carboxylate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.4500(10)
_cell_angle_beta                 113.9870(10)
_cell_angle_gamma                97.645(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0665(2)
_cell_length_b                   9.3351(2)
_cell_length_c                   10.5408(3)
_cell_measurement_reflns_used    6289
_cell_measurement_temperature    100
_cell_measurement_theta_max      34.30
_cell_measurement_theta_min      2.36
_cell_volume                     723.22(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12406
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+0.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                2179
_reflns_number_total             2655
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5147.cif
_cod_data_source_block           I
_cod_database_code               2227309
_cod_database_fobs_code          2227309
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 0.53056(13) 0.32289(13) 0.13622(12) 0.0190(3) Uani d . 1 . .
O O2 0.52454(14) 0.14419(13) 0.23468(13) 0.0247(3) Uani d . 1 . .
N N1 0.85134(17) 0.68033(16) 0.57591(15) 0.0199(3) Uani d . 1 . .
N N2 0.87235(16) 0.58254(15) 0.64872(15) 0.0169(3) Uani d . 1 . .
C C1 0.8628(2) 0.18877(19) 0.56614(19) 0.0203(4) Uani d . 1 . .
H H1A 0.9334 0.2079 0.5259 0.024 Uiso calc R 1 . .
C C2 0.8544(2) 0.0604(2) 0.60345(19) 0.0223(4) Uani d . 1 . .
H H2A 0.9206 -0.0053 0.5895 0.027 Uiso calc R 1 . .
C C3 0.7477(2) 0.02988(19) 0.66145(19) 0.0216(4) Uani d . 1 . .
H H3A 0.7430 -0.0557 0.6872 0.026 Uiso calc R 1 . .
C C4 0.6484(2) 0.12657(19) 0.68093(19) 0.0209(4) Uani d . 1 . .
H H4A 0.5754 0.1050 0.7183 0.025 Uiso calc R 1 . .
C C5 0.65692(19) 0.25632(19) 0.64487(18) 0.0187(4) Uani d . 1 . .
H H5A 0.5899 0.3213 0.6583 0.022 Uiso calc R 1 . .
C C6 0.76584(19) 0.28886(19) 0.58869(18) 0.0166(4) Uani d . 1 . .
C C7 0.77480(19) 0.42591(18) 0.54764(18) 0.0160(3) Uani d . 1 . .
C C8 0.69038(19) 0.42220(19) 0.40266(18) 0.0166(4) Uani d . 1 . .
C C9 0.7435(2) 0.58270(19) 0.42835(19) 0.0190(4) Uani d . 1 . .
H H9A 0.7070 0.6163 0.3507 0.023 Uiso calc R 1 . .
C C10 0.98019(19) 0.66369(19) 0.82223(18) 0.0178(4) Uani d . 1 . .
C C11 0.8627(2) 0.6922(2) 0.89211(19) 0.0233(4) Uani d . 1 . .
H H11A 0.7959 0.7535 0.8527 0.035 Uiso calc R 1 . .
H H11B 0.9299 0.7508 1.0030 0.035 Uiso calc R 1 . .
H H11C 0.7884 0.5902 0.8646 0.035 Uiso calc R 1 . .
C C12 1.0849(2) 0.5612(2) 0.87611(19) 0.0213(4) Uani d . 1 . .
H H12A 1.1484 0.5365 0.8219 0.032 Uiso calc R 1 . .
H H12B 1.0101 0.4628 0.8548 0.032 Uiso calc R 1 . .
H H12C 1.1623 0.6199 0.9856 0.032 Uiso calc R 1 . .
C C13 1.1020(2) 0.8262(2) 0.8701(2) 0.0232(4) Uani d . 1 . .
H H13A 1.0376 0.8944 0.8428 0.035 Uiso calc R 1 . .
H H13B 1.1678 0.8091 0.8175 0.035 Uiso calc R 1 . .
H H13C 1.1771 0.8768 0.9802 0.035 Uiso calc R 1 . .
C C14 0.57491(19) 0.2808(2) 0.25368(19) 0.0178(4) Uani d . 1 . .
C C15 0.4271(2) 0.19063(19) -0.01920(18) 0.0204(4) Uani d . 1 . .
H H15A 0.3269 0.1272 -0.0275 0.024 Uiso calc R 1 . .
H H15B 0.4921 0.1206 -0.0422 0.024 Uiso calc R 1 . .
C C16 0.3759(2) 0.2633(2) -0.1304(2) 0.0261(4) Uani d . 1 . .
H H16A 0.3137 0.1788 -0.2348 0.039 Uiso calc R 1 . .
H H16B 0.4759 0.3313 -0.1164 0.039 Uiso calc R 1 . .
H H16C 0.3051 0.3263 -0.1112 0.039 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
C14 O1 C15 . . 115.77(12) ?
C9 N1 N2 . . 105.07(12) ?
C7 N2 N1 . . 111.67(12) ?
C7 N2 C10 . . 131.06(13) ?
N1 N2 C10 . . 116.93(12) ?
C2 C1 C6 . . 120.21(15) ?
C2 C1 H1A . . 119.9 ?
C6 C1 H1A . . 119.9 ?
C3 C2 C1 . . 120.18(16) ?
C3 C2 H2A . . 119.9 ?
C1 C2 H2A . . 119.9 ?
C4 C3 C2 . . 119.92(15) ?
C4 C3 H3A . . 120.0 ?
C2 C3 H3A . . 120.0 ?
C3 C4 C5 . . 120.25(15) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C4 C5 C6 . . 120.01(15) ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C1 C6 C5 . . 119.40(14) ?
C1 C6 C7 . . 119.91(14) ?
C5 C6 C7 . . 120.65(14) ?
N2 C7 C8 . . 106.22(13) ?
N2 C7 C6 . . 125.57(14) ?
C8 C7 C6 . . 128.21(14) ?
C7 C8 C9 . . 105.09(14) ?
C7 C8 C14 . . 127.70(14) ?
C9 C8 C14 . . 127.19(14) ?
N1 C9 C8 . . 111.93(14) ?
N1 C9 H9A . . 124.0 ?
C8 C9 H9A . . 124.0 ?
N2 C10 C12 . . 110.47(13) ?
N2 C10 C11 . . 108.18(12) ?
C12 C10 C11 . . 111.78(13) ?
N2 C10 C13 . . 108.24(12) ?
C12 C10 C13 . . 108.71(13) ?
C11 C10 C13 . . 109.39(14) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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 ?
O2 C14 O1 . . 123.37(14) ?
O2 C14 C8 . . 126.18(14) ?
O1 C14 C8 . . 110.45(13) ?
O1 C15 C16 . . 107.43(13) ?
O1 C15 H15A . . 110.2 ?
C16 C15 H15A . . 110.2 ?
O1 C15 H15B . . 110.2 ?
C16 C15 H15B . . 110.2 ?
H15A C15 H15B . . 108.5 ?
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 ?
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 C14 . 1.3511(18) ?
O1 C15 . 1.4550(18) ?
O2 C14 . 1.2116(18) ?
N1 C9 . 1.320(2) ?
N1 N2 . 1.3695(17) ?
N2 C7 . 1.363(2) ?
N2 C10 . 1.502(2) ?
C1 C2 . 1.388(2) ?
C1 C6 . 1.391(2) ?
C1 H1A . 0.93 ?
C2 C3 . 1.386(2) ?
C2 H2A . 0.93 ?
C3 C4 . 1.380(2) ?
C3 H3A . 0.93 ?
C4 C5 . 1.392(2) ?
C4 H4A . 0.93 ?
C5 C6 . 1.393(2) ?
C5 H5A . 0.93 ?
C6 C7 . 1.489(2) ?
C7 C8 . 1.388(2) ?
C8 C9 . 1.403(2) ?
C8 C14 . 1.467(2) ?
C9 H9A . 0.93 ?
C10 C12 . 1.524(2) ?
C10 C11 . 1.524(2) ?
C10 C13 . 1.530(2) ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C15 C16 . 1.499(2) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
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
_geom_hbond_publ_flag
C15 H15B O2 2_655 0.97 2.53 3.367(2) 145 yes
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
C9 N1 N2 C7 . . . . -1.56(17) ?
C9 N1 N2 C10 . . . . -175.57(13) ?
C6 C1 C2 C3 . . . . 0.9(2) ?
C1 C2 C3 C4 . . . . 0.5(2) ?
C2 C3 C4 C5 . . . . -1.0(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C2 C1 C6 C5 . . . . -1.8(2) ?
C2 C1 C6 C7 . . . . -179.70(15) ?
C4 C5 C6 C1 . . . . 1.3(2) ?
C4 C5 C6 C7 . . . . 179.20(14) ?
N1 N2 C7 C8 . . . . 1.46(17) ?
C10 N2 C7 C8 . . . . 174.38(15) ?
N1 N2 C7 C6 . . . . -179.31(14) ?
C10 N2 C7 C6 . . . . -6.4(3) ?
C1 C6 C7 N2 . . . . -97.7(2) ?
C5 C6 C7 N2 . . . . 84.4(2) ?
C1 C6 C7 C8 . . . . 81.3(2) ?
C5 C6 C7 C8 . . . . -96.5(2) ?
N2 C7 C8 C9 . . . . -0.76(17) ?
C6 C7 C8 C9 . . . . -179.96(15) ?
N2 C7 C8 C14 . . . . 177.44(15) ?
C6 C7 C8 C14 . . . . -1.8(3) ?
N2 N1 C9 C8 . . . . 1.04(18) ?
C7 C8 C9 N1 . . . . -0.18(18) ?
C14 C8 C9 N1 . . . . -178.40(15) ?
C7 N2 C10 C12 . . . . 44.2(2) ?
N1 N2 C10 C12 . . . . -143.23(13) ?
C7 N2 C10 C11 . . . . -78.5(2) ?
N1 N2 C10 C11 . . . . 94.12(15) ?
C7 N2 C10 C13 . . . . 163.07(15) ?
N1 N2 C10 C13 . . . . -24.31(18) ?
C15 O1 C14 O2 . . . . -4.6(2) ?
C15 O1 C14 C8 . . . . 175.15(12) ?
C7 C8 C14 O2 . . . . 5.7(3) ?
C9 C8 C14 O2 . . . . -176.47(16) ?
C7 C8 C14 O1 . . . . -174.06(14) ?
C9 C8 C14 O1 . . . . 3.8(2) ?
C14 O1 C15 C16 . . . . 173.80(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745707
