#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/64/2016474.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_2016474
loop_
_publ_author_name
'Noe, Eric A.'
'Pawar, Diwakar M.'
'Fronczek, Frank R.'
_publ_section_title
;
 Cyclopentadecanone 2,4-dinitrophenylhydrazone
;
_journal_coeditor_code           AV3135
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o139
_journal_page_last               o141
_journal_paper_doi               10.1107/S0108270108002898
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C21 H32 N4 O4'
_chemical_formula_moiety         'C21 H32 N4 O4'
_chemical_formula_sum            'C21 H32 N4 O4'
_chemical_formula_weight         404.51
_chemical_name_systematic
;
Cyclopentadecanone 2,4-dinitrophenylhydrazone
;
_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                103.419(12)
_cell_angle_beta                 94.044(9)
_cell_angle_gamma                97.017(13)
_cell_formula_units_Z            2
_cell_length_a                   7.2486(14)
_cell_length_b                   8.3234(15)
_cell_length_c                   17.731(3)
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    90
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      2.5
_cell_volume                     1027.3(3)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type
'Nonius KappaCCD with an Oxford Cryosystems Cryostream cooler'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16738
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         29.3
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.0153(16)
_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   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.091
_refine_ls_R_factor_gt           0.051
_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)+(0.0302P)²+0.5298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.104
_reflns_number_gt                3372
_reflns_number_total             4936
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3135.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2016474
_cod_database_fobs_code          2016474
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
O O1 0.87072(16) 0.10477(14) 0.48047(7) 0.0192(3) Uani d . 1
O O2 0.82365(18) 0.18914(16) 0.37503(7) 0.0236(3) Uani d . 1
O O3 0.28483(19) 0.41631(16) 0.31370(7) 0.0272(3) Uani d . 1
O O4 0.10538(18) 0.49862(15) 0.40401(8) 0.0252(3) Uani d . 1
N N1 0.56818(19) 0.14734(16) 0.65874(8) 0.0139(3) Uani d . 1
N N2 0.6406(2) 0.15332(17) 0.58880(8) 0.0135(3) Uani d . 1
H H2N 0.745(3) 0.117(2) 0.5767(10) 0.016 Uiso d . 1
N N3 0.77557(19) 0.16912(16) 0.43770(8) 0.0144(3) Uani d . 1
N N4 0.2347(2) 0.42481(17) 0.37939(9) 0.0186(3) Uani d . 1
C C1 0.6738(2) 0.10401(19) 0.70983(9) 0.0135(3) Uani d . 1
C C2 0.5831(2) 0.0806(2) 0.78126(9) 0.0168(4) Uani d . 1
H H2A 0.5843 -0.0365 0.7845 0.020 Uiso calc R 1
H H2B 0.4508 0.0977 0.7744 0.020 Uiso calc R 1
C C3 0.6735(2) 0.1958(2) 0.85892(9) 0.0161(4) Uani d . 1
H H3A 0.6269 0.1504 0.9020 0.019 Uiso calc R 1
H H3B 0.8102 0.1951 0.8616 0.019 Uiso calc R 1
C C4 0.6354(2) 0.3759(2) 0.87123(10) 0.0165(4) Uani d . 1
H H4A 0.4991 0.3783 0.8708 0.020 Uiso calc R 1
H H4B 0.6790 0.4216 0.8277 0.020 Uiso calc R 1
C C5 0.7340(2) 0.4855(2) 0.94836(10) 0.0179(4) Uani d . 1
H H5A 0.8694 0.4781 0.9491 0.021 Uiso calc R 1
H H5B 0.6876 0.4397 0.9914 0.021 Uiso calc R 1
C C6 0.7079(3) 0.6702(2) 0.96427(10) 0.0202(4) Uani d . 1
H H6A 0.5732 0.6773 0.9547 0.024 Uiso calc R 1
H H6B 0.7477 0.7234 1.0200 0.024 Uiso calc R 1
C C7 0.8160(2) 0.7686(2) 0.91478(10) 0.0188(4) Uani d . 1
H H7A 0.7699 0.8774 0.9197 0.023 Uiso calc R 1
H H7B 0.7912 0.7067 0.8594 0.023 Uiso calc R 1
C C8 1.0267(2) 0.7994(2) 0.93815(10) 0.0170(4) Uani d . 1
H H8A 1.0697 0.6914 0.9392 0.020 Uiso calc R 1
H H8B 1.0519 0.8719 0.9916 0.020 Uiso calc R 1
C C9 1.1408(3) 0.8806(2) 0.88389(10) 0.0177(4) Uani d . 1
H H9A 1.2691 0.9222 0.9095 0.021 Uiso calc R 1
H H9B 1.0838 0.9777 0.8750 0.021 Uiso calc R 1
C C10 1.1509(2) 0.7599(2) 0.80525(10) 0.0177(4) Uani d . 1
H H10A 1.1948 0.8246 0.7680 0.021 Uiso calc R 1
H H10B 1.0239 0.7011 0.7846 0.021 Uiso calc R 1
C C11 1.2819(2) 0.6303(2) 0.81037(10) 0.0178(4) Uani d . 1
H H11A 1.4118 0.6807 0.8083 0.021 Uiso calc R 1
H H11B 1.2756 0.6013 0.8613 0.021 Uiso calc R 1
C C12 1.2348(2) 0.4698(2) 0.74518(10) 0.0161(4) Uani d . 1
H H12A 1.2054 0.4999 0.6953 0.019 Uiso calc R 1
H H12B 1.3462 0.4117 0.7402 0.019 Uiso calc R 1
C C13 1.0700(2) 0.3500(2) 0.75891(10) 0.0164(4) Uani d . 1
H H13A 1.1003 0.3163 0.8078 0.020 Uiso calc R 1
H H13B 0.9587 0.4082 0.7650 0.020 Uiso calc R 1
C C14 1.0251(2) 0.1951(2) 0.69174(9) 0.0149(3) Uani d . 1
H H14A 1.1406 0.1437 0.6837 0.018 Uiso calc R 1
H H14B 0.9894 0.2307 0.6439 0.018 Uiso calc R 1
C C15 0.8694(2) 0.0602(2) 0.70121(10) 0.0155(4) Uani d . 1
H H15A 0.8616 -0.0356 0.6554 0.019 Uiso calc R 1
H H15B 0.9095 0.0210 0.7476 0.019 Uiso calc R 1
C C16 0.5419(2) 0.21265(19) 0.53597(9) 0.0122(3) Uani d . 1
C C17 0.6019(2) 0.22337(19) 0.46248(9) 0.0131(3) Uani d . 1
C C18 0.5001(2) 0.28929(19) 0.41090(9) 0.0141(3) Uani d . 1
H H18 0.5424 0.2945 0.3619 0.017 Uiso calc R 1
C C19 0.3366(2) 0.3470(2) 0.43182(10) 0.0154(4) Uani d . 1
C C20 0.2703(2) 0.33826(19) 0.50314(10) 0.0158(4) Uani d . 1
H H20 0.1567 0.3783 0.5165 0.019 Uiso calc R 1
C C21 0.3707(2) 0.27143(19) 0.55347(10) 0.0145(3) Uani d . 1
H H21 0.3243 0.2643 0.6015 0.017 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
_geom_angle_publ_flag
C1 N1 N2 116.64(14) y
C16 N2 N1 118.84(13) y
C16 N2 H2N 118.5(12) ?
N1 N2 H2N 122.7(12) ?
O2 N3 O1 122.26(13) ?
O2 N3 C17 118.65(13) ?
O1 N3 C17 119.08(13) ?
O4 N4 O3 123.67(14) ?
O4 N4 C19 117.92(14) ?
O3 N4 C19 118.39(14) ?
N1 C1 C2 115.12(15) ?
N1 C1 C15 126.35(15) ?
C2 C1 C15 118.28(14) ?
C1 C2 C3 115.75(14) ?
C1 C2 H2A 108.3 ?
C3 C2 H2A 108.3 ?
C1 C2 H2B 108.3 ?
C3 C2 H2B 108.3 ?
H2A C2 H2B 107.4 ?
C4 C3 C2 114.20(13) ?
C4 C3 H3A 108.7 ?
C2 C3 H3A 108.7 ?
C4 C3 H3B 108.7 ?
C2 C3 H3B 108.7 ?
H3A C3 H3B 107.6 ?
C3 C4 C5 111.68(14) ?
C3 C4 H4A 109.3 ?
C5 C4 H4A 109.3 ?
C3 C4 H4B 109.3 ?
C5 C4 H4B 109.3 ?
H4A C4 H4B 107.9 ?
C4 C5 C6 115.09(14) ?
C4 C5 H5A 108.5 ?
C6 C5 H5A 108.5 ?
C4 C5 H5B 108.5 ?
C6 C5 H5B 108.5 ?
H5A C5 H5B 107.5 ?
C7 C6 C5 114.39(14) ?
C7 C6 H6A 108.7 ?
C5 C6 H6A 108.7 ?
C7 C6 H6B 108.7 ?
C5 C6 H6B 108.7 ?
H6A C6 H6B 107.6 ?
C6 C7 C8 112.98(14) ?
C6 C7 H7A 109.0 ?
C8 C7 H7A 109.0 ?
C6 C7 H7B 109.0 ?
C8 C7 H7B 109.0 ?
H7A C7 H7B 107.8 ?
C7 C8 C9 114.12(14) ?
C7 C8 H8A 108.7 ?
C9 C8 H8A 108.7 ?
C7 C8 H8B 108.7 ?
C9 C8 H8B 108.7 ?
H8A C8 H8B 107.6 ?
C8 C9 C10 112.57(14) ?
C8 C9 H9A 109.1 ?
C10 C9 H9A 109.1 ?
C8 C9 H9B 109.1 ?
C10 C9 H9B 109.1 ?
H9A C9 H9B 107.8 ?
C9 C10 C11 113.02(14) ?
C9 C10 H10A 109.0 ?
C11 C10 H10A 109.0 ?
C9 C10 H10B 109.0 ?
C11 C10 H10B 109.0 ?
H10A C10 H10B 107.8 ?
C12 C11 C10 113.54(14) ?
C12 C11 H11A 108.9 ?
C10 C11 H11A 108.9 ?
C12 C11 H11B 108.9 ?
C10 C11 H11B 108.9 ?
H11A C11 H11B 107.7 ?
C13 C12 C11 113.54(14) ?
C13 C12 H12A 108.9 ?
C11 C12 H12A 108.9 ?
C13 C12 H12B 108.9 ?
C11 C12 H12B 108.9 ?
H12A C12 H12B 107.7 ?
C14 C13 C12 111.64(14) ?
C14 C13 H13A 109.3 ?
C12 C13 H13A 109.3 ?
C14 C13 H13B 109.3 ?
C12 C13 H13B 109.3 ?
H13A C13 H13B 108.0 ?
C13 C14 C15 116.41(14) ?
C13 C14 H14A 108.2 ?
C15 C14 H14A 108.2 ?
C13 C14 H14B 108.2 ?
C15 C14 H14B 108.2 ?
H14A C14 H14B 107.3 ?
C1 C15 C14 118.89(13) ?
C1 C15 H15A 107.6 ?
C14 C15 H15A 107.6 ?
C1 C15 H15B 107.6 ?
C14 C15 H15B 107.6 ?
H15A C15 H15B 107.0 ?
N2 C16 C21 119.99(14) ?
N2 C16 C17 123.59(14) ?
C21 C16 C17 116.41(14) ?
C18 C17 C16 121.98(15) ?
C18 C17 N3 116.03(14) ?
C16 C17 N3 121.98(14) ?
C19 C18 C17 118.87(15) ?
C19 C18 H18 120.6 ?
C17 C18 H18 120.6 ?
C18 C19 C20 121.52(15) ?
C18 C19 N4 118.87(15) ?
C20 C19 N4 119.57(14) ?
C21 C20 C19 119.28(15) ?
C21 C20 H20 120.4 ?
C19 C20 H20 120.4 ?
C20 C21 C16 121.92(15) ?
C20 C21 H21 119.0 ?
C16 C21 H21 119.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N3 1.2420(17) ?
O2 N3 1.2289(17) ?
O3 N4 1.2334(19) ?
O4 N4 1.2329(18) ?
N1 C1 1.288(2) y
N1 N2 1.3891(19) y
N2 C16 1.356(2) y
N2 H2N 0.869(18) ?
N3 C17 1.451(2) ?
N4 C19 1.459(2) ?
C1 C2 1.508(2) ?
C1 C15 1.516(2) ?
C2 C3 1.533(2) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C4 1.526(2) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.529(2) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.535(2) ?
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 C7 1.526(2) ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 C8 1.529(2) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C9 1.531(2) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.530(2) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 C11 1.535(2) ?
C10 H10A 0.9900 ?
C10 H10B 0.9900 ?
C11 C12 1.534(2) ?
C11 H11A 0.9900 ?
C11 H11B 0.9900 ?
C12 C13 1.531(2) ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
C13 C14 1.522(2) ?
C13 H13A 0.9900 ?
C13 H13B 0.9900 ?
C14 C15 1.539(2) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
C16 C21 1.417(2) ?
C16 C17 1.421(2) ?
C17 C18 1.385(2) ?
C18 C19 1.375(2) ?
C18 H18 0.9500 ?
C19 C20 1.399(2) ?
C20 C21 1.369(2) ?
C20 H20 0.9500 ?
C21 H21 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2N O1 0.869(18) 1.979(18) 2.6254(18) 130.2(15)
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
_geom_torsion_publ_flag
C15 C1 C2 C3 66.69(18) y
C1 C2 C3 C4 73.82(18) y
C2 C3 C4 C5 -178.22(14) y
C3 C4 C5 C6 178.25(15) y
C4 C5 C6 C7 -72.9(2) y
C5 C6 C7 C8 -71.38(19) y
C6 C7 C8 C9 173.55(14) y
C7 C8 C9 C10 -72.99(18) y
C8 C9 C10 C11 -74.00(19) y
C9 C10 C11 C12 155.55(15) y
C10 C11 C12 C13 -78.94(18) y
C11 C12 C13 C14 178.42(14) y
C12 C13 C14 C15 176.39(14) y
C14 C15 C1 C2 -122.89(16) y
C13 C14 C15 C1 61.5(2) y
N1 C1 C15 C14 63.3(2) y
C1 N1 N2 C16 -174.11(15) y
N2 N1 C1 C2 -173.57(13) ?
N2 N1 C1 C15 0.4(2) ?
N1 C1 C2 C3 -118.78(16) ?
N1 N2 C16 C21 1.7(2) ?
N1 N2 C16 C17 -179.59(14) ?
N2 C16 C17 C18 -178.05(16) ?
C21 C16 C17 C18 0.7(2) ?
N2 C16 C17 N3 0.6(2) ?
C21 C16 C17 N3 179.36(14) ?
O2 N3 C17 C18 2.2(2) ?
O1 N3 C17 C18 -178.08(14) ?
O2 N3 C17 C16 -176.59(15) ?
O1 N3 C17 C16 3.2(2) ?
C16 C17 C18 C19 0.4(2) ?
N3 C17 C18 C19 -178.32(14) ?
C17 C18 C19 C20 -0.9(2) ?
C17 C18 C19 N4 176.66(15) ?
O4 N4 C19 C18 -168.96(15) ?
O3 N4 C19 C18 9.5(2) ?
O4 N4 C19 C20 8.7(2) ?
O3 N4 C19 C20 -172.85(15) ?
C18 C19 C20 C21 0.3(2) ?
N4 C19 C20 C21 -177.29(15) ?
C19 C20 C21 C16 0.9(2) ?
N2 C16 C21 C20 177.43(15) ?
C17 C16 C21 C20 -1.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21118948
