#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003552.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_2003552
loop_
_publ_author_name
'Kendi, E.'
'\"Ozbey, S.'
'Ide, S.'
'Fun, H.-K.'
'Yip, B.-C.'
_publ_section_title
;
 The Phenylhydrazone Form of 2-(4-Chlorophenylazo)-1,3-indandione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1144
_journal_page_last               1146
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C15 H9 Cl1 N2 O2'
_chemical_formula_sum            'C15 H9 Cl N2 O2'
_chemical_formula_weight         284.7
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'SHELXTL-Plus (Sheldrick, 1991)'
_cell_angle_alpha                90.
_cell_angle_beta                 95.03(1)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   10.888(2)
_cell_length_b                   9.329(1)
_cell_length_c                   12.628(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      7.5
_cell_volume                     1277.7(3)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3294
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.244
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.22
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2149
_refine_ls_R_factor_obs          0.0476
_refine_ls_shift/esd_max         <0.1
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 1/[\s^2^(F) + 0.0002F^2^]'
_refine_ls_wR_factor_obs         0.0567
_reflns_number_observed          2149
_reflns_number_total             2949
_reflns_observed_criterion       F>4\s(F)
_[local]_cod_data_source_file    ha1116.cif
_[local]_cod_data_source_block   ha1116a
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_chemical_formula_sum_orig 'C15 H9 Cl1 N2 O2'
_cod_database_code               2003552
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-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
Cl .9710(1) .1631(1) .3148(1) .098(1)
N(1) 1.3705(2) .5807(2) .4222(1) .047(1)
N(2) 1.3786(2) .6507(2) .5130(1) .047(1)
O(1) 1.4054(2) .8331(2) .6994(1) .061(1)
O(2) 1.5927(1) .7278(2) .3845(1) .061(1)
C(1') 1.2736(2) .4830(2) .3988(2) .047(1)
C(2') 1.2694(2) .4077(3) .3037(2) .053(1)
C(3') 1.1769(2) .3098(3) .2780(2) .062(1)
C(4') 1.0876(2) .2875(3) .3469(2) .064(1)
C(5') 1.0917(2) .3610(3) .4422(3) .071(1)
C(6') 1.1838(2) .4587(3) .4680(2) .061(1)
C(1) 1.5706(2) .7806(2) .4695(2) .047(1)
C(2) 1.4678(2) .7435(2) .5320(2) .046(1)
C(3) 1.4774(2) .8315(2) .6301(2) .049(1)
C(4) 1.5886(2) .9210(2) .6248(2) .049(1)
C(5) 1.6384(2) 1.0210(3) .6975(2) .059(1)
C(6) 1.7441(3) 1.0923(3) .6733(2) .067(1)
C(7) 1.7971(2) 1.0663(3) .5795(2) .067(1)
C(8) 1.7474(2) .9659(3) .5071(2) .059(1)
C(9) 1.6428(2) .8934(2) .5305(2) .048(1)
H(1N) 1.4212(21) .6016(25) .3729(20) .066(7)
H(2') 1.3309(19) .4244(22) .2565(18) .055(6)
H(3') 1.1782(23) .2511(30) .2173(21) .082(8)
H(5') 1.0301(26) .3478(26) .4883(23) .085(9)
H(6') 1.1887(23) .5095(26) .5308(21) .075(8)
H(5) 1.5980(21) 1.0418(24) .7654(19) .067(7)
H(6) 1.7809(24) 1.1629(27) .7230(22) .077(8)
H(7) 1.8663(22) 1.1135(25) .5605(19) .061(7)
H(8) 1.7834(21) .9440(24) .4459(21) .067(7)
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
N(2) N(1) C(1') 119.8(2) yes
N(1) C(1') C(2') 118.5(2) yes
C(2') C(1') C(6') 119.3(2) yes
C(2') C(3') C(4') 119.6(2) yes
Cl C(4') C(5') 120.0(2) yes
C(4') C(5') C(6') 120.2(3) yes
N(2) C(2) C(3) 121.2(2) yes
C(3) C(2) C(1) 108.5(2) yes
O(1) C(3) C(4) 127.1(2) yes
C(3) C(4) C(5) 128.7(2) yes
C(5) C(4) C(9) 121.2(2) yes
C(5) C(6) C(7) 121.4(2) yes
C(7) C(8) C(9) 118.2(2) yes
C(4) C(9) C(1) 109.1(2) yes
O(2) C(1) C(2) 126.5(2) yes
C(2) C(1) C(9) 106.4(2) yes
N(1) N(2) C(2) 118.8(2) yes
N(1) C(1') C(6') 122.2(2) yes
C(1') C(2') C(3') 120.5(2) yes
Cl C(4') C(3') 119.7(2) yes
C(3') C(4') C(5') 120.3(2) yes
C(1') C(6') C(5') 120.0(2) yes
N(2) C(2) C(1) 130.3(2) yes
O(1) C(3) C(2) 127.0(2) yes
C(2) C(3) C(4) 105.9(2) yes
C(3) C(4) C(9) 110.1(2) yes
C(4) C(5) C(6) 117.4(2) yes
C(6) C(7) C(8) 121.0(2) yes
C(4) C(9) C(8) 120.7(2) yes
C(8) C(9) C(1) 130.2(2) yes
O(2) C(1) C(9) 127.1(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(4') 1.741(3) yes
N(1) C(1') 1.405(3) yes
O(1) C(3) 1.225(3) yes
C(1') C(2') 1.389(3) yes
C(2') C(3') 1.377(3) yes
C(4') C(5') 1.383(4) yes
C(2) C(3) 1.482(3) yes
C(3) C(4) 1.477(3) yes
C(4) C(9) 1.398(3) yes
C(6) C(7) 1.384(4) yes
C(8) C(9) 1.379(3) yes
N(1) N(2) 1.315(2) yes
N(2) C(2) 1.307(3) yes
O(2) C(1) 1.224(3) yes
C(1') C(6') 1.386(3) yes
C(3') C(4') 1.375(4) yes
C(5') C(6') 1.373(4) yes
C(2) C(1) 1.466(3) yes
C(4) C(5) 1.386(3) yes
C(5) C(6) 1.387(4) yes
C(7) C(8) 1.385(4) yes
C(9) C(1) 1.487(3) yes
_journal_paper_doi 10.1107/S0108270194012047