#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/62/2206267.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_2206267
loop_
_publ_author_name
'Li-Rong Wen'
'Zi-Qin Ke'
'Bo Qu'
'Ming Li'
_publ_section_title
;
 Ethyl 3-[(1,5-dimethylpyrazol-4-yl)carbonylhydrazino]butyrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2018
_journal_page_last               o2019
_journal_paper_doi               10.1107/S160053680501679X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H18 N4 O3'
_chemical_formula_moiety         'C12 H18 N4 O3'
_chemical_formula_sum            'C12 H18 N4 O3'
_chemical_formula_weight         266.30
_chemical_name_systematic
;
Ethyl 3-[(1,5-dimethylpyrazol-4-yl)carbonylhydrazino]butyrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5212(18)
_cell_length_b                   7.9018(12)
_cell_length_c                   30.551(5)
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.18
_cell_measurement_theta_min      2.21
_cell_volume                     2781.3(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker,  1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18790
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0744P)²+1.2421P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                1751
_reflns_number_total             2452
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6079.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_type_symbol
O1 0.96141(16) 0.2037(2) 0.50899(5) 0.0706(5) Uani d . 1 O
O2 1.1309(2) 0.1061(3) 0.69988(6) 0.0908(7) Uani d . 1 O
O3 0.99426(19) -0.0885(2) 0.70803(6) 0.0830(6) Uani d . 1 O
N1 0.95960(19) 0.4952(3) 0.63866(7) 0.0699(6) Uani d . 1 N
N2 0.89508(17) 0.5617(2) 0.60565(7) 0.0625(5) Uani d . 1 N
N3 1.04079(17) 0.0450(2) 0.56091(6) 0.0552(5) Uani d D 1 N
H3D 1.051(2) -0.030(2) 0.5405(6) 0.066 Uiso d D 1 H
N4 1.06353(16) 0.0116(2) 0.60468(6) 0.0537(5) Uani d . 1 N
C1 1.0010(2) 0.3540(3) 0.62243(8) 0.0598(6) Uani d . 1 C
H1 1.0489 0.2805 0.6379 0.072 Uiso calc R 1 H
C2 0.8330(2) 0.7196(4) 0.61368(10) 0.0830(8) Uani d . 1 C
H2A 0.8494 0.7983 0.5906 0.124 Uiso calc R 1 H
H2B 0.8576 0.7667 0.6411 0.124 Uiso calc R 1 H
H2C 0.7511 0.6977 0.6146 0.124 Uiso calc R 1 H
C3 0.8298(2) 0.5152(4) 0.52953(9) 0.0754(8) Uani d . 1 C
H3A 0.8330 0.4247 0.5086 0.113 Uiso calc R 1 H
H3B 0.8632 0.6154 0.5170 0.113 Uiso calc R 1 H
H3C 0.7504 0.5369 0.5372 0.113 Uiso calc R 1 H
C4 0.89607(19) 0.4665(3) 0.56953(8) 0.0558(6) Uani d . 1 C
C5 0.96499(18) 0.3260(3) 0.57917(7) 0.0512(5) Uani d . 1 C
C6 0.98835(19) 0.1896(3) 0.54815(7) 0.0529(6) Uani d . 1 C
C7 1.12428(19) -0.1188(3) 0.61344(7) 0.0534(5) Uani d . 1 C
C8 1.1765(2) -0.2389(4) 0.58153(8) 0.0716(7) Uani d . 1 C
H8A 1.1159 -0.2964 0.5659 0.107 Uiso calc R 1 H
H8B 1.2231 -0.3202 0.5969 0.107 Uiso calc R 1 H
H8C 1.2242 -0.1776 0.5612 0.107 Uiso calc R 1 H
C9 1.1451(2) -0.1561(3) 0.66077(7) 0.0691(7) Uani d . 1 C
H9A 1.2282 -0.1590 0.6660 0.083 Uiso calc R 1 H
H9B 1.1144 -0.2675 0.6674 0.083 Uiso calc R 1 H
C10 1.0913(3) -0.0302(3) 0.69132(7) 0.0657(7) Uani d . 1 C
C11 0.9300(4) 0.0158(5) 0.73975(11) 0.1059(11) Uani d . 1 C
H11A 0.8965 -0.0567 0.7620 0.127 Uiso calc R 1 H
H11B 0.9832 0.0932 0.7540 0.127 Uiso calc R 1 H
C12 0.8407(4) 0.1092(7) 0.71902(15) 0.1454(17) Uani d . 1 C
H12A 0.8739 0.1830 0.6975 0.218 Uiso calc R 1 H
H12B 0.8000 0.1752 0.7405 0.218 Uiso calc R 1 H
H12C 0.7875 0.0326 0.7051 0.218 Uiso calc R 1 H
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
_geom_angle_publ_flag
C10 O3 C11 119.2(2) ?
C1 N1 N2 104.3(2) yes
C4 N2 N1 113.01(19) yes
C4 N2 C2 128.7(2) ?
N1 N2 C2 118.3(2) ?
C6 N3 N4 121.57(19) ?
C6 N3 H3D 115.5(12) ?
N4 N3 H3D 122.5(12) ?
C7 N4 N3 117.38(19) ?
N1 C1 C5 112.5(2) yes
N1 C1 H1 123.7 ?
C5 C1 H1 123.7 ?
N2 C2 H2A 109.5 ?
N2 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
N2 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C4 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C4 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
N2 C4 C5 106.15(19) yes
N2 C4 C3 121.8(2) ?
C5 C4 C3 132.0(2) ?
C4 C5 C1 104.0(2) yes
C4 C5 C6 123.7(2) ?
C1 C5 C6 132.3(2) ?
O1 C6 N3 117.8(2) ?
O1 C6 C5 120.9(2) ?
N3 C6 C5 121.33(19) ?
N4 C7 C8 126.9(2) ?
N4 C7 C9 116.8(2) ?
C8 C7 C9 116.3(2) ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C7 C9 C10 113.9(2) ?
C7 C9 H9A 108.8 ?
C10 C9 H9A 108.8 ?
C7 C9 H9B 108.8 ?
C10 C9 H9B 108.8 ?
H9A C9 H9B 107.7 ?
O2 C10 O3 123.6(2) ?
O2 C10 C9 125.1(3) ?
O3 C10 C9 111.2(2) ?
C12 C11 O3 111.3(3) ?
C12 C11 H11A 109.4 ?
O3 C11 H11A 109.4 ?
C12 C11 H11B 109.4 ?
O3 C11 H11B 109.4 ?
H11A C11 H11B 108.0 ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 1.241(3) ?
O2 C10 1.199(3) ?
O3 C10 1.313(3) ?
O3 C11 1.471(4) ?
N1 C1 1.311(3) yes
N1 N2 1.359(3) yes
N2 C4 1.336(3) yes
N2 C2 1.459(3) ?
N3 C6 1.350(3) ?
N3 N4 1.388(2) yes
N3 H3D 0.868(17) ?
N4 C7 1.274(3) yes
C1 C5 1.403(3) yes
C1 H1 0.9300 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C4 1.492(3) ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 C5 1.396(3) yes
C5 C6 1.460(3) ?
C7 C8 1.488(3) ?
C7 C9 1.495(3) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 C10 1.498(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C11 C12 1.416(5) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 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
_geom_hbond_publ_flag
N3 H3D O1 5_756 0.868(17) 2.047(17) 2.901(3) 168(?) yes
C8 H8A O1 5_756 0.96 2.56 3.205(3) 124 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
C1 N1 N2 C4 -0.4(3)
C1 N1 N2 C2 178.1(2)
C6 N3 N4 C7 -172.6(2)
N2 N1 C1 C5 0.1(3)
N1 N2 C4 C5 0.6(3)
C2 N2 C4 C5 -177.7(2)
N1 N2 C4 C3 179.3(2)
C2 N2 C4 C3 1.0(4)
N2 C4 C5 C1 -0.5(2)
C3 C4 C5 C1 -179.0(2)
N2 C4 C5 C6 179.9(2)
C3 C4 C5 C6 1.4(4)
N1 C1 C5 C4 0.3(3)
N1 C1 C5 C6 179.9(2)
N4 N3 C6 O1 -173.57(19)
N4 N3 C6 C5 7.1(3)
C4 C5 C6 O1 10.7(3)
C1 C5 C6 O1 -168.8(2)
C4 C5 C6 N3 -170.0(2)
C1 C5 C6 N3 10.5(4)
N3 N4 C7 C8 1.5(3)
N3 N4 C7 C9 -178.23(18)
N4 C7 C9 C10 -0.7(3)
C8 C7 C9 C10 179.5(2)
C11 O3 C10 O2 -1.2(4)
C11 O3 C10 C9 178.5(2)
C7 C9 C10 O2 -79.4(3)
C7 C9 C10 O3 101.0(2)
C10 O3 C11 C12 96.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24734105
