#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:05:46 +0200 (mar 06 de oct de 2020) $
#$Revision: 257739 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/94/7059415.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_7059415
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         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 108.849(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7144(13)
_cell_length_b                   4.6497(3)
_cell_length_c                   14.7226(10)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      3.12
_cell_volume                     1341.97(15)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25638
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.788
_diffrn_reflns_theta_min         2.769
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,BRUKER
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: METHANOL'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0494
_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)+(0.0456P)²+0.9913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3190
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04339j2.cif
_cod_data_source_block           AMPNQ
_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/c'
_cod_database_code               7059415
_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   0.981
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.38013(5) 0.6315(2) 0.38888(7) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.26609(5) 0.6111(2) 0.66579(7) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.14328(5) 0.4489(2) 0.48827(8) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.26732(6) 0.9255(3) 0.35734(8) 0.0152(2) Uani 1 1 d . . . . .
N2 N 0.19363(6) 0.8849(2) 0.50260(8) 0.0117(2) Uani 1 1 d . . . . .
C1 C 0.35326(6) 0.6126(3) 0.45112(9) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.28776(6) 0.7775(3) 0.43968(9) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.25787(6) 0.7597(3) 0.51063(9) 0.0115(2) Uani 1 1 d . . . . .
C4 C 0.28945(6) 0.6018(3) 0.59897(9) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.37562(7) 0.2387(3) 0.68631(9) 0.0158(3) Uani 1 1 d . . . . .
H5 H 0.3546 0.2340 0.7349 0.019 Uiso 1 1 calc R U . . .
C6 C 0.43181(7) 0.0658(3) 0.69408(10) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.4487 -0.0594 0.7475 0.022 Uiso 1 1 calc R U . . .
C7 C 0.46344(7) 0.0754(3) 0.62390(10) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.5024 -0.0408 0.6301 0.022 Uiso 1 1 calc R U . . .
C8 C 0.43824(7) 0.2544(3) 0.54470(10) 0.0164(3) Uani 1 1 d . . . . .
H8 H 0.4598 0.2605 0.4967 0.020 Uiso 1 1 calc R U . . .
C9 C 0.38119(6) 0.4250(3) 0.53607(9) 0.0131(3) Uani 1 1 d . . . . .
C10 C 0.35011(6) 0.4191(3) 0.60716(9) 0.0127(3) Uani 1 1 d . . . . .
C11 C 0.20501(7) 1.0931(3) 0.31678(9) 0.0158(3) Uani 1 1 d . . . . .
H11A H 0.2121 1.2332 0.2702 0.019 Uiso 1 1 calc R U . . .
H11B H 0.1957 1.2028 0.3688 0.019 Uiso 1 1 calc R U . . .
C12 C 0.14325(7) 0.9067(3) 0.26647(10) 0.0187(3) Uani 1 1 d . . . . .
H12A H 0.1513 0.8040 0.2122 0.022 Uiso 1 1 calc R U . . .
H12B H 0.1370 0.7613 0.3120 0.022 Uiso 1 1 calc R U . . .
C13 C 0.07894(8) 1.0887(4) 0.22916(13) 0.0324(4) Uani 1 1 d . . . . .
H13A H 0.0710 1.1905 0.2828 0.049 Uiso 1 1 calc R U . . .
H13B H 0.0399 0.9640 0.1981 0.049 Uiso 1 1 calc R U . . .
H13C H 0.0846 1.2288 0.1825 0.049 Uiso 1 1 calc R U . . .
C14 C 0.14018(7) 0.7118(3) 0.49622(9) 0.0138(3) Uani 1 1 d . . . . .
C15 C 0.07464(7) 0.8540(3) 0.49515(10) 0.0174(3) Uani 1 1 d . . . . .
H15A H 0.0411 0.8383 0.4308 0.026 Uiso 1 1 calc R U . . .
H15B H 0.0832 1.0573 0.5123 0.026 Uiso 1 1 calc R U . . .
H15C H 0.0570 0.7588 0.5417 0.026 Uiso 1 1 calc R U . . .
H2N H 0.1877(9) 1.072(4) 0.5080(13) 0.020(4) Uiso 1 1 d . . . . .
H1N H 0.2909(10) 0.891(4) 0.3175(14) 0.025(5) Uiso 1 1 d . . . . .
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
C2 N1 C11 128.62(11) . . ?
C2 N1 H1N 115.1(13) . . ?
C11 N1 H1N 115.3(12) . . ?
C14 N2 C3 119.17(11) . . ?
C14 N2 H2N 117.3(12) . . ?
C3 N2 H2N 123.1(12) . . ?
O1 C1 C9 121.90(12) . . ?
O1 C1 C2 119.24(12) . . ?
C9 C1 C2 118.82(11) . . ?
N1 C2 C3 129.01(12) . . ?
N1 C2 C1 111.69(11) . . ?
C3 C2 C1 119.30(11) . . ?
C2 C3 N2 123.36(11) . . ?
C2 C3 C4 121.78(11) . . ?
N2 C3 C4 114.83(11) . . ?
O2 C4 C3 121.27(12) . . ?
O2 C4 C10 119.70(12) . . ?
C3 C4 C10 119.01(11) . . ?
C6 C5 C10 119.91(13) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 120.24(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.18(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.63(13) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.23(12) . . ?
C8 C9 C1 120.02(12) . . ?
C10 C9 C1 119.74(11) . . ?
C5 C10 C9 119.78(12) . . ?
C5 C10 C4 119.54(11) . . ?
C9 C10 C4 120.67(11) . . ?
N1 C11 C12 112.80(11) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.00(13) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N2 122.18(12) . . ?
O3 C14 C15 120.63(12) . . ?
N2 C14 C15 117.15(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 1.2194(16) . ?
O2 C4 1.2293(16) . ?
O3 C14 1.2313(17) . ?
N1 C2 1.3381(16) . ?
N1 C11 1.4601(17) . ?
N1 H1N 0.89(2) . ?
N2 C14 1.3474(17) . ?
N2 C3 1.4219(16) . ?
N2 H2N 0.89(2) . ?
C1 C9 1.4809(18) . ?
C1 C2 1.5196(17) . ?
C2 C3 1.3781(17) . ?
C3 C4 1.4523(17) . ?
C4 C10 1.4890(18) . ?
C5 C6 1.3885(19) . ?
C5 C10 1.3939(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3946(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3950(18) . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5056(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
C11 N1 C2 C3 -4.8(2) . . . . ?
C11 N1 C2 C1 175.28(12) . . . . ?
O1 C1 C2 N1 0.89(18) . . . . ?
C9 C1 C2 N1 -176.88(11) . . . . ?
O1 C1 C2 C3 -179.06(12) . . . . ?
C9 C1 C2 C3 3.17(18) . . . . ?
N1 C2 C3 N2 5.9(2) . . . . ?
C1 C2 C3 N2 -174.21(11) . . . . ?
N1 C2 C3 C4 -176.08(13) . . . . ?
C1 C2 C3 C4 3.86(19) . . . . ?
C14 N2 C3 C2 112.19(14) . . . . ?
C14 N2 C3 C4 -66.00(15) . . . . ?
C2 C3 C4 O2 172.51(13) . . . . ?
N2 C3 C4 O2 -9.26(18) . . . . ?
C2 C3 C4 C10 -9.19(19) . . . . ?
N2 C3 C4 C10 169.03(11) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C8 -1.1(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C1 -178.95(12) . . . . ?
O1 C1 C9 C8 -2.6(2) . . . . ?
C2 C1 C9 C8 175.10(12) . . . . ?
O1 C1 C9 C10 177.54(13) . . . . ?
C2 C1 C9 C10 -4.75(18) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
C6 C5 C10 C4 179.44(12) . . . . ?
C8 C9 C10 C5 -0.99(19) . . . . ?
C1 C9 C10 C5 178.86(12) . . . . ?
C8 C9 C10 C4 179.60(12) . . . . ?
C1 C9 C10 C4 -0.55(18) . . . . ?
O2 C4 C10 C5 6.38(19) . . . . ?
C3 C4 C10 C5 -171.94(12) . . . . ?
O2 C4 C10 C9 -174.21(12) . . . . ?
C3 C4 C10 C9 7.47(18) . . . . ?
C2 N1 C11 C12 -80.10(17) . . . . ?
N1 C11 C12 C13 177.51(12) . . . . ?
C3 N2 C14 O3 -6.80(19) . . . . ?
C3 N2 C14 C15 175.64(11) . . . . ?
