#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/12/2011287.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_2011287
loop_
_publ_author_name
'Lu, Zhong-Lin'
'Xiao, Wen'
'Chen, Zhong-Ning'
'Gong, Xiao-Yang'
'Shanmuga Sundara Raj, S.'
'Razak, Ibrahim Abdul'
'Fun, Hoong-Kun'
_publ_section_title
;
 4,5-Diazafluoren-9-one benzoylhydrazone monohydrate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1017
_journal_page_last               1018
_journal_paper_doi               10.1107/S0108270100007459
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C18 H12 N4 O, H2 O'
_chemical_formula_sum            'C18 H14 N4 O2'
_chemical_formula_weight         318.33
_chemical_name_systematic
;
4,5-Diaza-9-fluorenone Benzoylhydrazone Monohydrate
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.9290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4880(2)
_cell_length_b                   22.7523(2)
_cell_length_c                   8.7810(2)
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.79
_cell_volume                     1537.80(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL  and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .971
_diffrn_measured_fraction_theta_max .971
_diffrn_measurement_device_type
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0780
_diffrn_reflns_av_sigmaI/netI    .1010
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10723
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    .093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .12
_refine_diff_density_max         .290
_refine_diff_density_min         -.278
_refine_ls_extinction_coef       .014(2)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   .930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .930
_refine_ls_R_factor_all          .1153
_refine_ls_R_factor_gt           .0614
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1207
_reflns_number_gt                1870
_reflns_number_total             3729
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk1396.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2011287
_cod_database_fobs_code          2011287
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 1.2290(2) .57696(9) -.1370(2) .0388(5) Uani d . 1 . . N
N2 1.2709(2) .52004(8) .1917(2) .0379(5) Uani d . 1 . . N
N3 .7533(2) .64431(9) -.0334(2) .0394(5) Uani d . 1 . . N
N4 .6726(2) .64123(9) .0728(3) .0422(5) Uani d . 1 . . N
H4A .7005 .6151 .1506 .051 Uiso calc R 1 . . H
O1 .5059(2) .71954(9) -.0606(2) .0633(6) Uani d . 1 . . O
C1 1.1873(3) .61027(11) -.2742(3) .0474(7) Uani d . 1 . . C
H1A 1.2598 .6086 -.3293 .057 Uiso calc R 1 . . H
C2 1.0443(4) .64703(12) -.3401(3) .0511(7) Uani d . 1 . . C
H2A 1.0233 .6691 -.4359 .061 Uiso calc R 1 . . H
C3 .9327(3) .65059(11) -.2620(3) .0444(6) Uani d . 1 . . C
H3A .8347 .6745 -.3039 .053 Uiso calc R 1 . . H
C4 .9730(3) .61730(10) -.1199(3) .0339(5) Uani d . 1 . . C
C5 .8896(3) .61279(10) -.0029(3) .0343(5) Uani d . 1 . . C
C6 1.0022(3) .57315(10) .1337(3) .0318(5) Uani d . 1 . . C
C7 1.0036(3) .55506(11) .2851(3) .0406(6) Uani d . 1 . . C
H7A .9170 .5665 .3174 .049 Uiso calc R 1 . . H
C8 1.1394(3) .51917(11) .3863(3) .0445(6) Uani d . 1 . . C
H8A 1.1458 .5065 .4895 .053 Uiso calc R 1 . . H
C9 1.2649(3) .50218(11) .3345(3) .0434(6) Uani d . 1 . . C
H9A 1.3512 .4766 .4032 .052 Uiso calc R 1 . . H
C10 1.1398(3) .55455(10) .0955(3) .0306(5) Uani d . 1 . . C
C11 1.1208(3) .58223(10) -.0623(3) .0328(5) Uani d . 1 . . C
C12 .5447(3) .68221(11) .0484(3) .0420(6) Uani d . 1 . . C
C13 .4626(3) .68010(10) .1692(3) .0416(6) Uani d . 1 . . C
C14 .3023(3) .70743(11) .1213(4) .0505(7) Uani d . 1 . . C
H14A .2461 .7235 .0143 .061 Uiso calc R 1 . . H
C15 .2264(4) .71070(12) .2336(4) .0612(8) Uani d . 1 . . C
H15A .1180 .7283 .2007 .073 Uiso calc R 1 . . H
C16 .3093(4) .68845(13) .3912(5) .0650(8) Uani d . 1 . . C
H16A .2591 .6922 .4665 .078 Uiso calc R 1 . . H
C17 .4663(4) .66050(13) .4403(4) .0638(8) Uani d . 1 . . C
H17A .5206 .6443 .5473 .077 Uiso calc R 1 . . H
C18 .5440(3) .65644(12) .3289(4) .0529(7) Uani d . 1 . . C
H18A .6508 .6378 .3620 .063 Uiso calc R 1 . . H
O1W .6154(2) .52798(9) .1980(2) .0484(5) Uani d . 1 . . O
H1W1 .636(4) .4933(15) .152(4) .089(11) Uiso d . 1 . . H
H2W1 .502(5) .5253(15) .173(5) .113(14) Uiso d . 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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 C11 114.5(2) ?
C10 N2 C9 114.97(19) ?
C5 N3 N4 119.4(2) y
N3 N4 C12 116.5(2) y
N3 N4 H4A 121.8 ?
C12 N4 H4A 121.8 ?
N1 C1 C2 124.8(2) ?
N1 C1 H1A 117.6 ?
C2 C1 H1A 117.6 ?
C1 C2 C3 119.3(2) ?
C1 C2 H2A 120.3 ?
C3 C2 H2A 120.3 ?
C4 C3 C2 117.2(2) ?
C4 C3 H3A 121.4 ?
C2 C3 H3A 121.4 ?
C3 C4 C11 119.2(2) ?
C3 C4 C5 131.4(2) ?
C11 C4 C5 109.31(19) ?
N3 C5 C4 117.9(2) ?
N3 C5 C6 136.2(2) ?
C4 C5 C6 105.69(18) ?
C7 C6 C10 117.8(2) ?
C7 C6 C5 134.2(2) ?
C10 C6 C5 107.83(19) ?
C8 C7 C6 117.2(2) ?
C8 C7 H7A 121.4 ?
C6 C7 H7A 121.4 ?
C9 C8 C7 120.2(2) ?
C9 C8 H8A 119.9 ?
C7 C8 H8A 119.9 ?
N2 C9 C8 124.3(2) ?
N2 C9 H9A 117.9 ?
C8 C9 H9A 117.9 ?
N2 C10 C6 125.4(2) ?
N2 C10 C11 125.61(19) ?
C6 C10 C11 108.87(19) ?
N1 C11 C4 125.0(2) ?
N1 C11 C10 126.7(2) ?
C4 C11 C10 108.27(18) ?
O1 C12 N4 122.0(2) y
O1 C12 C13 121.8(2) y
N4 C12 C13 116.1(2) y
C18 C13 C14 119.2(2) ?
C18 C13 C12 123.3(2) ?
C14 C13 C12 117.4(2) ?
C15 C14 C13 119.8(3) ?
C15 C14 H14A 120.1 ?
C13 C14 H14A 120.1 ?
C16 C15 C14 120.5(3) ?
C16 C15 H15A 119.8 ?
C14 C15 H15A 119.8 ?
C15 C16 C17 120.7(3) ?
C15 C16 H16A 119.6 ?
C17 C16 H16A 119.6 ?
C16 C17 C18 119.6(3) ?
C16 C17 H17A 120.2 ?
C18 C17 H17A 120.2 ?
C13 C18 C17 120.2(2) ?
C13 C18 H18A 119.9 ?
C17 C18 H18A 119.9 ?
H1W1 O1W H2W1 102(3) ?
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
N1 C1 . 1.339(3) y
N1 C11 . 1.340(3) y
N2 C10 . 1.332(3) y
N2 C9 . 1.339(3) y
N3 C5 . 1.290(3) y
N3 N4 . 1.371(3) y
N4 C12 . 1.378(3) y
N4 H4A . .8600 ?
O1 C12 . 1.216(3) y
C1 C2 . 1.384(4) ?
C1 H1A . .9300 ?
C2 C3 . 1.387(3) ?
C2 H2A . .9300 ?
C3 C4 . 1.374(3) ?
C3 H3A . .9300 ?
C4 C11 . 1.390(3) ?
C4 C5 . 1.476(3) ?
C5 C6 . 1.483(3) ?
C6 C7 . 1.387(3) ?
C6 C10 . 1.410(3) ?
C7 C8 . 1.386(3) ?
C7 H7A . .9300 ?
C8 C9 . 1.379(3) ?
C8 H8A . .9300 ?
C9 H9A . .9300 ?
C10 C11 . 1.467(3) ?
C12 C13 . 1.496(3) ?
C13 C18 . 1.384(4) ?
C13 C14 . 1.390(3) ?
C14 C15 . 1.390(4) ?
C14 H14A . .9300 ?
C15 C16 . 1.358(4) ?
C15 H15A . .9300 ?
C16 C17 . 1.372(4) ?
C16 H16A . .9300 ?
C17 C18 . 1.394(4) ?
C17 H17A . .9300 ?
C18 H18A . .9300 ?
O1W H1W1 . .94(4) ?
O1W H2W1 . .90(4) ?
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
N4 H4A O1W 1_555 .86 2.21 2.921(3) 140 yes
O1W H1W1 N1 3_765 .94(3) 2.00(4) 2.886(3) 157(3) yes
O1W H2W1 N2 1_455 .89(5) 2.04(5) 2.907(3) 163(4) 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
_geom_torsion_publ_flag
C5 N3 N4 C12 170.4(2) y
C11 N1 C1 C2 -1.0(4) ?
N1 C1 C2 C3 -.2(4) ?
C1 C2 C3 C4 .8(4) ?
C2 C3 C4 C11 -.1(4) ?
C2 C3 C4 C5 176.6(2) ?
N4 N3 C5 C4 -179.95(19) ?
N4 N3 C5 C6 -5.5(4) ?
C3 C4 C5 N3 .6(4) ?
C11 C4 C5 N3 177.5(2) ?
C3 C4 C5 C6 -175.4(2) ?
C11 C4 C5 C6 1.5(3) ?
N3 C5 C6 C7 -.7(5) ?
C4 C5 C6 C7 174.2(2) ?
N3 C5 C6 C10 -176.4(3) ?
C4 C5 C6 C10 -1.5(2) ?
C10 C6 C7 C8 -1.0(3) ?
C5 C6 C7 C8 -176.4(2) ?
C6 C7 C8 C9 -.8(4) ?
C10 N2 C9 C8 -2.7(3) ?
C7 C8 C9 N2 2.9(4) ?
C9 N2 C10 C6 .7(3) ?
C9 N2 C10 C11 176.8(2) ?
C7 C6 C10 N2 1.1(3) ?
C5 C6 C10 N2 177.6(2) ?
C7 C6 C10 C11 -175.5(2) ?
C5 C6 C10 C11 1.0(2) ?
C1 N1 C11 C4 1.9(3) ?
C1 N1 C11 C10 -175.5(2) ?
C3 C4 C11 N1 -1.4(4) ?
C5 C4 C11 N1 -178.7(2) ?
C3 C4 C11 C10 176.4(2) ?
C5 C4 C11 C10 -.9(3) ?
N2 C10 C11 N1 1.0(4) ?
C6 C10 C11 N1 177.6(2) ?
N2 C10 C11 C4 -176.7(2) ?
C6 C10 C11 C4 -.1(3) ?
N3 N4 C12 O1 -.6(3) y
N3 N4 C12 C13 -177.6(2) y
O1 C12 C13 C18 -153.0(3) ?
N4 C12 C13 C18 24.0(4) ?
O1 C12 C13 C14 22.0(4) ?
N4 C12 C13 C14 -161.0(2) ?
C18 C13 C14 C15 .1(4) ?
C12 C13 C14 C15 -175.1(2) ?
C13 C14 C15 C16 1.4(4) ?
C14 C15 C16 C17 -2.4(4) ?
C15 C16 C17 C18 1.9(5) ?
C14 C13 C18 C17 -.5(4) ?
C12 C13 C18 C17 174.4(3) ?
C16 C17 C18 C13 -.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107252
