#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:05:46 +0200 (mar 06 de oct de 2020) $
#$Revision: 257739 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/94/7059416.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_7059416
loop_
_publ_author_name
'Choudhari, Dinkar'
'Salunke-Gawali, Sunita'
'Chakravarty, Debamitra'
'Shaikh, Samir R.'
'Lande, Dipali N.'
'Gejji, Shridhar P.'
'Rao, Pradeep Kumar'
'Satpute, Surekha'
'Puranik, Vedavati G.'
'Gonnade, Rajesh'
_publ_section_title
;
 Synthesis and biological activity of imidazole based 1,4-naphthoquinones
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6889
_journal_page_last               6901
_journal_paper_doi               10.1039/C9NJ04339J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-05 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1220(3)
_cell_length_b                   15.5877(5)
_cell_length_c                   9.2916(3)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.37
_cell_measurement_theta_min      2.90
_cell_volume                     1138.78(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17799
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.902
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: METHANOL'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0434P)²+0.8241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2511
_reflns_number_total             2731
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04339j2.cif
_cod_data_source_block           mo_IMENQ_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059413--7059419.cif.

 Adding full bibliography for 7059413--7059419.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7059416
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05598(12) 0.44033(6) 0.31497(10) 0.0223(2) Uani 1 1 d . . . . .
O2 O 0.48138(12) 0.58158(6) 0.80370(10) 0.0237(2) Uani 1 1 d . . . . .
N1 N 0.20423(12) 0.61814(6) 0.31719(11) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.38322(13) 0.67432(6) 0.51898(11) 0.0168(2) Uani 1 1 d . . . . .
C12 C 0.18179(17) 0.57704(10) 0.05423(14) 0.0245(3) Uani 1 1 d . . . . .
H12A H 0.2731 0.6163 0.0458 0.037 Uiso 1 1 calc R U . . .
H12B H 0.1004 0.5712 -0.0429 0.037 Uiso 1 1 calc R U . . .
H12C H 0.2302 0.5207 0.0876 0.037 Uiso 1 1 calc R U . . .
C11 C 0.09135(15) 0.61242(8) 0.16606(12) 0.0174(2) Uani 1 1 d . . . . .
H11A H 0.0465 0.6702 0.1337 0.021 Uiso 1 1 calc R U . . .
H11B H -0.0065 0.5750 0.1681 0.021 Uiso 1 1 calc R U . . .
C2 C 0.23260(14) 0.55586(7) 0.42550(12) 0.0142(2) Uani 1 1 d . . . . .
C1 C 0.15944(15) 0.47047(7) 0.42211(13) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.21892(15) 0.42168(7) 0.56492(13) 0.0153(2) Uani 1 1 d . . . . .
C8 C 0.16011(16) 0.33807(8) 0.57113(14) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.0850 0.3136 0.4859 0.023 Uiso 1 1 calc R U . . .
C7 C 0.21039(17) 0.29016(8) 0.70084(15) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.1723 0.2327 0.7036 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31697(16) 0.32689(8) 0.82666(15) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.3509 0.2944 0.9157 0.025 Uiso 1 1 calc R U . . .
C3 C 0.34194(15) 0.59221(7) 0.54813(13) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.29831(15) 0.68775(8) 0.37871(13) 0.0161(2) Uani 1 1 d . . . . .
C14 C 0.30146(18) 0.76955(8) 0.29735(14) 0.0221(3) Uani 1 1 d . . . . .
H14A H 0.1862 0.7933 0.2669 0.033 Uiso 1 1 calc R U . . .
H14B H 0.3438 0.7588 0.2091 0.033 Uiso 1 1 calc R U . . .
H14C H 0.3765 0.8106 0.3624 0.033 Uiso 1 1 calc R U . . .
C4 C 0.39337(15) 0.54808(7) 0.69154(13) 0.0161(2) Uani 1 1 d . . . . .
C10 C 0.32775(15) 0.45822(7) 0.69171(13) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.37399(15) 0.41058(8) 0.82299(13) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.4447 0.4355 0.9100 0.022 Uiso 1 1 calc R U . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C2 106.30(9) . . ?
C13 N1 C11 126.51(10) . . ?
C2 N1 C11 127.17(10) . . ?
C13 N2 C3 104.41(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C11 C12 112.43(10) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C3 C2 N1 105.65(10) . . ?
C3 C2 C1 124.67(10) . . ?
N1 C2 C1 129.59(10) . . ?
O1 C1 C2 124.21(11) . . ?
O1 C1 C9 121.86(11) . . ?
C2 C1 C9 113.92(10) . . ?
C8 C9 C10 119.64(11) . . ?
C8 C9 C1 118.21(11) . . ?
C10 C9 C1 122.13(10) . . ?
C7 C8 C9 120.61(12) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C7 C6 119.55(12) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C5 C6 C7 120.49(11) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N2 C3 C2 111.10(10) . . ?
N2 C3 C4 126.29(10) . . ?
C2 C3 C4 122.47(11) . . ?
N2 C13 N1 112.53(10) . . ?
N2 C13 C14 124.27(11) . . ?
N1 C13 C14 123.19(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C4 C3 123.18(11) . . ?
O2 C4 C10 122.01(11) . . ?
C3 C4 C10 114.81(10) . . ?
C5 C10 C9 119.47(11) . . ?
C5 C10 C4 118.69(11) . . ?
C9 C10 C4 121.83(10) . . ?
C6 C5 C10 120.20(12) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2241(15) . ?
O2 C4 1.2232(15) . ?
N1 C13 1.3671(15) . ?
N1 C2 1.3755(14) . ?
N1 C11 1.4747(14) . ?
N2 C13 1.3294(15) . ?
N2 C3 1.3674(15) . ?
C12 C11 1.5186(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C3 1.3786(16) . ?
C2 C1 1.4548(16) . ?
C1 C9 1.5004(16) . ?
C9 C8 1.3942(17) . ?
C9 C10 1.4041(16) . ?
C8 C7 1.3894(18) . ?
C8 H8 0.9500 . ?
C7 C6 1.3916(19) . ?
C7 H7 0.9500 . ?
C6 C5 1.3876(17) . ?
C6 H6 0.9500 . ?
C3 C4 1.4643(16) . ?
C13 C14 1.4858(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C10 1.4988(16) . ?
C10 C5 1.3966(16) . ?
C5 H5 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C11 C12 92.45(14) . . . . ?
C2 N1 C11 C12 -89.44(14) . . . . ?
C13 N1 C2 C3 0.66(12) . . . . ?
C11 N1 C2 C3 -177.76(10) . . . . ?
C13 N1 C2 C1 177.28(12) . . . . ?
C11 N1 C2 C1 -1.14(19) . . . . ?
C3 C2 C1 O1 176.25(12) . . . . ?
N1 C2 C1 O1 0.2(2) . . . . ?
C3 C2 C1 C9 -2.35(17) . . . . ?
N1 C2 C1 C9 -178.40(11) . . . . ?
O1 C1 C9 C8 3.38(17) . . . . ?
C2 C1 C9 C8 -177.98(10) . . . . ?
O1 C1 C9 C10 -175.18(11) . . . . ?
C2 C1 C9 C10 3.46(16) . . . . ?
C10 C9 C8 C7 -1.05(18) . . . . ?
C1 C9 C8 C7 -179.65(11) . . . . ?
C9 C8 C7 C6 1.65(18) . . . . ?
C8 C7 C6 C5 -0.44(18) . . . . ?
C13 N2 C3 C2 0.20(13) . . . . ?
C13 N2 C3 C4 -175.53(11) . . . . ?
N1 C2 C3 N2 -0.55(13) . . . . ?
C1 C2 C3 N2 -177.38(10) . . . . ?
N1 C2 C3 C4 175.37(10) . . . . ?
C1 C2 C3 C4 -1.47(18) . . . . ?
C3 N2 C13 N1 0.24(13) . . . . ?
C3 N2 C13 C14 179.14(11) . . . . ?
C2 N1 C13 N2 -0.58(13) . . . . ?
C11 N1 C13 N2 177.85(10) . . . . ?
C2 N1 C13 C14 -179.49(11) . . . . ?
C11 N1 C13 C14 -1.06(18) . . . . ?
N2 C3 C4 O2 0.1(2) . . . . ?
C2 C3 C4 O2 -175.14(12) . . . . ?
N2 C3 C4 C10 179.33(11) . . . . ?
C2 C3 C4 C10 4.06(16) . . . . ?
C8 C9 C10 C5 -0.76(17) . . . . ?
C1 C9 C10 C5 177.78(11) . . . . ?
C8 C9 C10 C4 -179.42(11) . . . . ?
C1 C9 C10 C4 -0.88(17) . . . . ?
O2 C4 C10 C5 -2.33(18) . . . . ?
C3 C4 C10 C5 178.47(10) . . . . ?
O2 C4 C10 C9 176.34(11) . . . . ?
C3 C4 C10 C9 -2.86(16) . . . . ?
C7 C6 C5 C10 -1.38(18) . . . . ?
C9 C10 C5 C6 1.97(18) . . . . ?
C4 C10 C5 C6 -179.33(11) . . . . ?
