#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153816
loop_
_publ_author_name
'Prasad, Karothu Durga'
'Trinath, Jamma'
'Biswas, Ansuman'
'Sekar, Kanagaraj'
'Balaji, Kithiganahalli N.'
'Guru Row, Tayur N.'
_publ_section_title
;
 Alkyl chain substituted 1,9-pyrazoloanthrones exhibit prominent
 inhibitory effect on c-Jun N-terminal kinase (JNK).
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4656
_journal_page_last               4662
_journal_paper_doi               10.1039/c4ob00548a
_journal_volume                  12
_journal_year                    2014
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_chemical_name_systematic        ?
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      148
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   27.7895(8)
_cell_length_b                   27.7895(8)
_cell_length_c                   8.9482(3)
_cell_measurement_reflns_used    13435
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.4
_cell_volume                     5984.5(3)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'fω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13435
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                2239
_reflns_number_total             2914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00548a2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153814--7153819.cif.
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7153816
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 1/3+x,2/3+y,2/3+z
8 1/3-y,2/3+x-y,2/3+z
9 1/3-x+y,2/3-x,2/3+z
10 1/3-x,2/3-y,2/3-z
11 1/3+y,2/3-x+y,2/3-z
12 1/3+x-y,2/3+x,2/3-z
13 2/3+x,1/3+y,1/3+z
14 2/3-y,1/3+x-y,1/3+z
15 2/3-x+y,1/3-x,1/3+z
16 2/3-x,1/3-y,1/3-z
17 2/3+y,1/3-x+y,1/3-z
18 2/3+x-y,1/3+x,1/3-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O O 0.59554(5) 0.47401(5) 0.76025(14) 0.0367(3) Uani 1 1 d .
N2 N 0.42895(6) 0.52395(6) 0.75578(16) 0.0296(4) Uani 1 1 d .
N3 N 0.45396(5) 0.56719(6) 0.85527(15) 0.0304(4) Uani 1 1 d .
C4 C 0.46472(6) 0.50522(6) 0.73978(17) 0.0247(4) Uani 1 1 d .
C5 C 0.51219(6) 0.53641(6) 0.82770(17) 0.0232(4) Uani 1 1 d .
C6 C 0.50501(6) 0.57648(7) 0.90120(17) 0.0254(4) Uani 1 1 d .
C7 C 0.50645(6) 0.45003(6) 0.65987(17) 0.0252(4) Uani 1 1 d .
C8 C 0.50485(7) 0.40690(7) 0.57586(19) 0.0301(4) Uani 1 1 d .
H8 H 0.5340 0.3996 0.5831 0.036 Uiso 1 1 calc R
C9 C 0.46116(6) 0.46016(6) 0.64942(17) 0.0250(4) Uani 1 1 d .
C10 C 0.55706(7) 0.48402(7) 0.75696(18) 0.0263(4) Uani 1 1 d .
C11 C 0.55857(6) 0.53001(6) 0.84348(17) 0.0233(4) Uani 1 1 d .
C12 C 0.59983(7) 0.56721(7) 0.93951(17) 0.0264(4) Uani 1 1 d .
H12 H 0.6317 0.5649 0.9551 0.032 Uiso 1 1 calc R
C13 C 0.54674(7) 0.61429(7) 0.99689(18) 0.0287(4) Uani 1 1 d .
H13 H 0.5435 0.6419 1.0469 0.034 Uiso 1 1 calc R
C14 C 0.59316(7) 0.60827(7) 1.01299(18) 0.0285(4) Uani 1 1 d .
H14 H 0.6215 0.6328 1.0760 0.034 Uiso 1 1 calc R
C15 C 0.42605(8) 0.59756(8) 0.9002(2) 0.0401(5) Uani 1 1 d .
H15A H 0.4290 0.6027 1.0078 0.048 Uiso 1 1 calc R
H15B H 0.3869 0.5756 0.8754 0.048 Uiso 1 1 calc R
C16 C 0.41702(7) 0.38553(7) 0.46987(19) 0.0327(4) Uani 1 1 d .
H16 H 0.3876 0.3644 0.4053 0.039 Uiso 1 1 calc R
C17 C 0.46053(8) 0.37469(7) 0.48187(19) 0.0334(4) Uani 1 1 d .
H17 H 0.4599 0.3460 0.4271 0.040 Uiso 1 1 calc R
C18 C 0.41699(7) 0.42752(7) 0.55329(17) 0.0292(4) Uani 1 1 d .
H18 H 0.3874 0.4341 0.5453 0.035 Uiso 1 1 calc R
C19 C 0.45008(9) 0.65335(8) 0.8260(3) 0.0523(6) Uani 1 1 d .
H19A H 0.4457 0.6484 0.7185 0.063 Uiso 1 1 calc R
H19B H 0.4895 0.6750 0.8477 0.063 Uiso 1 1 calc R
C20 C 0.42165(10) 0.68449(10) 0.8799(4) 0.0824(10) Uani 1 1 d .
H20A H 0.4401 0.7213 0.8384 0.124 Uiso 1 1 calc R
H20B H 0.4233 0.6867 0.9870 0.124 Uiso 1 1 calc R
H20C H 0.3835 0.6652 0.8484 0.124 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
C4 N2 N3 105.07(13)
C6 N3 N2 112.48(13)
C6 N3 C15 127.37(15)
N2 N3 C15 120.15(14)
N2 C4 C5 110.55(14)
N2 C4 C9 130.57(15)
C5 C4 C9 118.88(14)
C6 C5 C11 124.50(15)
C6 C5 C4 107.04(13)
C11 C5 C4 128.46(15)
N3 C6 C5 104.86(14)
N3 C6 C13 135.60(15)
C5 C6 C13 119.54(14)
C8 C7 C9 118.85(15)
C8 C7 C10 117.70(15)
C9 C7 C10 123.44(14)
C17 C8 C7 121.13(16)
C18 C9 C7 119.23(15)
C18 C9 C4 124.13(15)
C7 C9 C4 116.63(14)
O C10 C11 122.03(15)
O C10 C7 120.83(15)
C11 C10 C7 117.12(13)
C12 C11 C5 116.03(15)
C12 C11 C10 128.53(14)
C5 C11 C10 115.44(14)
C11 C12 C14 119.82(14)
C14 C13 C6 116.32(15)
C13 C14 C12 123.79(15)
N3 C15 C19 112.60(16)
C18 C16 C17 120.54(16)
C8 C17 C16 119.72(16)
C16 C18 C9 120.51(16)
C15 C19 C20 111.07(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C10 1.2324(19)
N2 C4 1.341(2)
N2 N3 1.3728(19)
N3 C6 1.372(2)
N3 C15 1.459(2)
C4 C5 1.402(2)
C4 C9 1.452(2)
C5 C6 1.391(2)
C5 C11 1.394(2)
C6 C13 1.401(2)
C7 C8 1.397(2)
C7 C9 1.423(2)
C7 C10 1.515(2)
C8 C17 1.387(2)
C9 C18 1.399(2)
C10 C11 1.477(2)
C11 C12 1.392(2)
C12 C14 1.407(2)
C13 C14 1.389(2)
C15 C19 1.502(3)
C16 C18 1.386(2)
C16 C17 1.389(3)
C19 C20 1.513(3)
