#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/14/2201464.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_2201464
loop_
_publ_author_name
'Shang Shan'
'Duan-Jun Xu'
'Jing-Yun Wu'
'Michael Y. Chiang'
_publ_section_title
;
 Cyclopentanone 4-nitrophenylhydrazone
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1218
_journal_page_last               o1219
_journal_paper_doi               10.1107/S160053680201841X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C11 H13 N3 O2'
_chemical_formula_moiety         'C11 H13 N3 O2'
_chemical_formula_sum            'C11 H13 N3 O2'
_chemical_formula_weight         219.24
_chemical_name_systematic        ?
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.372(3)
_cell_length_b                   14.705(4)
_cell_length_c                   7.211(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.07
_cell_measurement_theta_min      4.39
_cell_volume                     2266.2(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω/2θ
_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  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2360
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0862P)²+0.1882P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1972
_reflns_number_gt                789
_reflns_number_total             2224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6152.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               2201464
_cod_database_fobs_code          2201464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.31816(12) 0.29629(18) 0.8614(6) 0.1294(13) Uani d . 1 . . O
O2 0.37818(13) 0.18363(19) 0.9198(6) 0.1315(13) Uani d . 1 . . O
N1 0.32661(15) 0.2152(2) 0.8849(6) 0.0930(11) Uani d . 1 . . N
N2 0.12358(11) -0.01858(17) 0.8275(4) 0.0709(9) Uani d . 1 . . N
H2A 0.1289 -0.0755 0.8500 0.085 Uiso calc R 1 . . H
N3 0.06469(12) 0.01408(17) 0.7798(4) 0.0681(8) Uani d . 1 . . N
C1 0.17287(14) 0.0401(2) 0.8386(4) 0.0593(8) Uani d . 1 . . C
C2 0.23131(14) 0.0074(2) 0.8927(6) 0.0720(10) Uani d . 1 . . C
H2 0.2363 -0.0540 0.9202 0.086 Uiso calc R 1 . . H
C3 0.28102(15) 0.0645(2) 0.9057(5) 0.0737(10) Uani d . 1 . . C
H3 0.3199 0.0420 0.9416 0.088 Uiso calc R 1 . . H
C4 0.27422(14) 0.1548(2) 0.8663(5) 0.0687(10) Uani d . 1 . . C
C5 0.21710(16) 0.1886(2) 0.8088(6) 0.0795(11) Uani d . 1 . . C
H5 0.2128 0.2499 0.7797 0.095 Uiso calc R 1 . . H
C6 0.16698(14) 0.1313(2) 0.7950(5) 0.0733(10) Uani d . 1 . . C
H6 0.1285 0.1539 0.7559 0.088 Uiso calc R 1 . . H
C7 0.02092(16) -0.0454(2) 0.7755(5) 0.0694(9) Uani d . 1 . . C
C8 0.02464(16) -0.1444(2) 0.8125(6) 0.0927(12) Uani d . 1 . . C
H8A 0.0400 -0.1560 0.9370 0.111 Uiso calc R 1 . . H
H8B 0.0521 -0.1742 0.7242 0.111 Uiso calc R 1 . . H
C9 -0.0420(2) -0.1775(3) 0.7909(9) 0.143(2) Uani d . 1 . . C
H9A -0.0429 -0.2337 0.7205 0.172 Uiso calc R 1 . . H
H9B -0.0605 -0.1886 0.9116 0.172 Uiso calc R 1 . . H
C10 -0.0762(2) -0.1079(4) 0.6950(8) 0.135(2) Uani d . 1 . . C
H10A -0.1188 -0.1053 0.7417 0.162 Uiso calc R 1 . . H
H10B -0.0779 -0.1218 0.5636 0.162 Uiso calc R 1 . . H
C11 -0.04477(15) -0.0184(3) 0.7238(5) 0.0834(11) Uani d . 1 . . C
H11A -0.0646 0.0157 0.8229 0.100 Uiso calc R 1 . . H
H11B -0.0453 0.0177 0.6113 0.100 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0873(19) 0.0593(17) 0.242(4) -0.0127(14) 0.008(2) 0.004(2)
O2 0.0691(18) 0.094(2) 0.232(4) -0.0164(16) -0.027(2) 0.020(2)
N1 0.064(2) 0.0660(19) 0.149(3) -0.0058(16) 0.007(2) 0.004(2)
N2 0.0501(15) 0.0577(15) 0.105(2) 0.0016(12) -0.0048(15) 0.0002(16)
N3 0.0511(16) 0.0747(18) 0.079(2) 0.0031(14) 0.0001(13) 0.0013(15)
C1 0.0522(18) 0.0565(17) 0.069(2) 0.0015(15) 0.0055(16) -0.0039(16)
C2 0.058(2) 0.0509(16) 0.107(3) 0.0037(17) -0.0096(19) 0.0077(19)
C3 0.0586(19) 0.060(2) 0.102(3) 0.0047(15) -0.0109(19) 0.005(2)
C4 0.0546(18) 0.0589(19) 0.093(3) -0.0048(16) 0.0050(18) -0.0001(19)
C5 0.065(2) 0.0499(19) 0.123(3) 0.0060(16) 0.007(2) 0.010(2)
C6 0.0520(18) 0.063(2) 0.105(3) 0.0063(16) 0.0002(18) 0.0078(18)
C7 0.057(2) 0.083(2) 0.068(2) -0.0023(18) 0.0031(17) -0.001(2)
C8 0.068(2) 0.081(2) 0.129(4) -0.0132(19) -0.004(2) -0.008(2)
C9 0.094(3) 0.111(4) 0.224(6) -0.031(3) -0.031(4) 0.010(4)
C10 0.088(3) 0.143(4) 0.175(6) -0.036(3) -0.039(3) 0.017(4)
C11 0.0522(19) 0.116(3) 0.082(3) 0.000(2) -0.0021(18) 0.002(2)
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
O1 N1 O2 122.3(3) ?
O1 N1 C4 118.5(3) ?
O2 N1 C4 119.2(3) ?
C1 N2 N3 119.7(2) yes
C1 N2 H2A 120.2 ?
N3 N2 H2A 120.2 ?
C7 N3 N2 115.6(3) yes
N2 C1 C6 122.0(3) ?
N2 C1 C2 119.3(3) ?
C6 C1 C2 118.7(3) ?
C3 C2 C1 120.5(3) ?
C3 C2 H2 119.8 ?
C1 C2 H2 119.8 ?
C2 C3 C4 120.2(3) ?
C2 C3 H3 119.9 ?
C4 C3 H3 119.9 ?
C3 C4 C5 120.4(3) ?
C3 C4 N1 119.9(3) ?
C5 C4 N1 119.6(3) ?
C6 C5 C4 119.5(3) ?
C6 C5 H5 120.2 ?
C4 C5 H5 120.2 ?
C5 C6 C1 120.6(3) ?
C5 C6 H6 119.7 ?
C1 C6 H6 119.7 ?
N3 C7 C8 128.8(3) ?
N3 C7 C11 120.5(3) ?
C8 C7 C11 110.7(3) ?
C7 C8 C9 104.3(3) ?
C7 C8 H8A 110.9 ?
C9 C8 H8A 110.9 ?
C7 C8 H8B 110.9 ?
C9 C8 H8B 110.9 ?
H8A C8 H8B 108.9 ?
C10 C9 C8 107.5(4) ?
C10 C9 H9A 110.2 ?
C8 C9 H9A 110.2 ?
C10 C9 H9B 110.2 ?
C8 C9 H9B 110.2 ?
H9A C9 H9B 108.5 ?
C9 C10 C11 109.4(4) ?
C9 C10 H10A 109.8 ?
C11 C10 H10A 109.8 ?
C9 C10 H10B 109.8 ?
C11 C10 H10B 109.8 ?
H10A C10 H10B 108.3 ?
C10 C11 C7 102.9(3) ?
C10 C11 H11A 111.2 ?
C7 C11 H11A 111.2 ?
C10 C11 H11B 111.2 ?
C7 C11 H11B 111.2 ?
H11A C11 H11B 109.1 ?
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 N1 . 1.218(4) ?
O2 N1 . 1.222(4) ?
N1 C4 . 1.436(4) yes
N2 C1 . 1.364(4) yes
N2 N3 . 1.390(3) yes
N2 H2A . 0.8600 ?
N3 C7 . 1.280(4) yes
C1 C6 . 1.384(4) ?
C1 C2 . 1.394(4) ?
C2 C3 . 1.357(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(4) ?
C5 C6 . 1.366(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.483(5) yes
C7 C11 . 1.505(5) yes
C8 C9 . 1.513(5) yes
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.435(6) yes
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.492(6) yes
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
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
N2 H2A O1 7_655 0.86 2.20 3.004(4) 155 yes
C2 H2 O1 7_655 0.93 2.53 3.287(4) 139 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9162960
