#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:05:46 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257739 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059413.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_7059413
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         'C16 H17 N2 O2'
_chemical_formula_sum            'C16 H17 N2 O2'
_chemical_formula_weight         269.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-09-19 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.460(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6578(15)
_cell_length_b                   8.7453(11)
_cell_length_c                   22.209(4)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.77
_cell_volume                     2730.2(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      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38016
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.743
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0668
_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)+(0.0668P)²+3.6578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1640
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04339j2.cif
_cod_data_source_block           2NA3ENQ
_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      'C 2/c'
_cod_database_code               7059413
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O2 O 0.13155(16) 0.0779(3) 0.05554(10) 0.0689(7) Uani 1 1 d . . . . .
O3 O -0.12700(16) 0.4445(3) -0.11700(10) 0.0670(7) Uani 1 1 d . . . . .
N1 N -0.03739(15) 0.2278(2) 0.07643(10) 0.0377(6) Uani 1 1 d . . . . .
N2 N -0.14143(16) 0.3812(3) 0.00635(11) 0.0457(6) Uani 1 1 d . . . . .
H2 H -0.1890 0.4394 -0.0109 0.055 Uiso 1 1 calc R U . . .
C1 C 0.07550(18) 0.1645(3) 0.01721(13) 0.0411(7) Uani 1 1 d . . . . .
C2 C -0.00665(18) 0.2388(3) 0.02635(12) 0.0364(6) Uani 1 1 d . . . . .
C3 C -0.07199(18) 0.3334(3) -0.01626(12) 0.0378(6) Uani 1 1 d . . . . .
C4 C -0.0672(2) 0.3657(3) -0.07753(12) 0.0416(7) Uani 1 1 d . . . . .
C5 C 0.0275(2) 0.3168(3) -0.14621(14) 0.0551(8) Uani 1 1 d . . . . .
H5 H -0.0158 0.3749 -0.1762 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1048(2) 0.2517(4) -0.15804(16) 0.0638(9) Uani 1 1 d . . . . .
H6 H 0.1137 0.2658 -0.1975 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1727(2) 0.1637(4) -0.11344(16) 0.0609(9) Uani 1 1 d . . . . .
H7 H 0.2247 0.1236 -0.1242 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1637(2) 0.1371(3) -0.05666(14) 0.0497(8) Uani 1 1 d . . . . .
H8 H 0.2079 0.0792 -0.0271 0.060 Uiso 1 1 calc R U . . .
C9 C 0.08515(19) 0.2002(3) -0.04396(13) 0.0403(7) Uani 1 1 d . . . . .
C10 C 0.01688(19) 0.2927(3) -0.08898(12) 0.0401(7) Uani 1 1 d . . . . .
C11 C -0.11869(19) 0.3167(3) 0.06177(12) 0.0394(7) Uani 1 1 d . . . . .
C12 C 0.00802(19) 0.1367(3) 0.13369(12) 0.0418(7) Uani 1 1 d . . . . .
H12A H 0.0324 0.0427 0.1209 0.050 Uiso 1 1 calc R U . . .
H12B H -0.0405 0.1090 0.1537 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0909(2) 0.2185(3) 0.18322(13) 0.0531(8) Uani 1 1 d . . . . .
H13A H 0.1361 0.2568 0.1623 0.064 Uiso 1 1 calc R U . . .
H13B H 0.0653 0.3058 0.2000 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1442(2) 0.1145(4) 0.23847(13) 0.0588(9) Uani 1 1 d . . . . .
H14A H 0.1848 0.1788 0.2707 0.071 Uiso 1 1 calc R U . . .
H14B H 0.0974 0.0685 0.2562 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2031(3) -0.0087(5) 0.22414(18) 0.0819(12) Uani 1 1 d . . . . .
H15A H 0.1636 -0.0773 0.1941 0.123 Uiso 1 1 calc R U . . .
H15B H 0.2335 -0.0636 0.2619 0.123 Uiso 1 1 calc R U . . .
H15C H 0.2505 0.0345 0.2070 0.123 Uiso 1 1 calc R U . . .
C16 C -0.1759(2) 0.3332(4) 0.10318(14) 0.0567(8) Uani 1 1 d . . . . .
H16A H -0.1371 0.3661 0.1436 0.085 Uiso 1 1 calc R U . . .
H16B H -0.2048 0.2369 0.1074 0.085 Uiso 1 1 calc R U . . .
H16C H -0.2246 0.4079 0.0866 0.085 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
C2 N1 C11 103.8(2) . . ?
C2 N1 C12 125.7(2) . . ?
C11 N1 C12 130.5(2) . . ?
C11 N2 C3 101.7(2) . . ?
C11 N2 H2 129.2 . . ?
C3 N2 H2 129.2 . . ?
O2 C1 C2 126.3(3) . . ?
O2 C1 C9 123.4(2) . . ?
C2 C1 C9 110.3(2) . . ?
N1 C2 C3 106.3(2) . . ?
N1 C2 C1 126.1(2) . . ?
C3 C2 C1 127.6(2) . . ?
N2 C3 C2 112.4(2) . . ?
N2 C3 C4 123.8(2) . . ?
C2 C3 C4 123.8(2) . . ?
O3 C4 C3 124.6(3) . . ?
O3 C4 C10 124.8(2) . . ?
C3 C4 C10 110.6(2) . . ?
C10 C5 C6 116.4(3) . . ?
C10 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C5 C6 C7 123.5(3) . . ?
C5 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 116.1(3) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C8 C9 C1 114.7(3) . . ?
C8 C9 C10 122.6(3) . . ?
C1 C9 C10 122.7(2) . . ?
C5 C10 C9 120.1(3) . . ?
C5 C10 C4 115.0(3) . . ?
C9 C10 C4 124.9(2) . . ?
N2 C11 N1 115.9(2) . . ?
N2 C11 C16 121.8(3) . . ?
N1 C11 C16 122.3(2) . . ?
N1 C12 C13 115.2(2) . . ?
N1 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N1 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 113.9(2) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 H14A 108.0 . . ?
C13 C14 H14A 108.0 . . ?
C15 C14 H14B 108.0 . . ?
C13 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
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 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O2 C1 1.256(3) . ?
O3 C4 1.255(3) . ?
N1 C2 1.317(3) . ?
N1 C11 1.383(3) . ?
N1 C12 1.488(3) . ?
N2 C11 1.308(3) . ?
N2 C3 1.324(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.433(4) . ?
C1 C9 1.439(4) . ?
C2 C3 1.408(3) . ?
C3 C4 1.411(4) . ?
C4 C10 1.473(4) . ?
C5 C10 1.340(4) . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.325(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.445(4) . ?
C11 C16 1.417(4) . ?
C12 C13 1.563(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.549(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.470(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 -0.5(3) . . . . ?
C12 N1 C2 C3 178.8(2) . . . . ?
C11 N1 C2 C1 -178.7(2) . . . . ?
C12 N1 C2 C1 0.6(4) . . . . ?
O2 C1 C2 N1 -0.5(5) . . . . ?
C9 C1 C2 N1 178.3(2) . . . . ?
O2 C1 C2 C3 -178.3(3) . . . . ?
C9 C1 C2 C3 0.5(4) . . . . ?
C11 N2 C3 C2 0.0(3) . . . . ?
C11 N2 C3 C4 176.3(3) . . . . ?
N1 C2 C3 N2 0.4(3) . . . . ?
C1 C2 C3 N2 178.6(2) . . . . ?
N1 C2 C3 C4 -176.0(2) . . . . ?
C1 C2 C3 C4 2.2(4) . . . . ?
N2 C3 C4 O3 1.0(4) . . . . ?
C2 C3 C4 O3 176.9(3) . . . . ?
N2 C3 C4 C10 -178.3(2) . . . . ?
C2 C3 C4 C10 -2.4(4) . . . . ?
C10 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C1 177.8(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
O2 C1 C9 C8 -2.8(4) . . . . ?
C2 C1 C9 C8 178.4(2) . . . . ?
O2 C1 C9 C10 176.2(3) . . . . ?
C2 C1 C9 C10 -2.6(4) . . . . ?
C6 C5 C10 C9 -0.7(4) . . . . ?
C6 C5 C10 C4 179.5(3) . . . . ?
C8 C9 C10 C5 1.7(4) . . . . ?
C1 C9 C10 C5 -177.2(3) . . . . ?
C8 C9 C10 C4 -178.6(3) . . . . ?
C1 C9 C10 C4 2.5(4) . . . . ?
O3 C4 C10 C5 0.6(4) . . . . ?
C3 C4 C10 C5 179.9(2) . . . . ?
O3 C4 C10 C9 -179.1(3) . . . . ?
C3 C4 C10 C9 0.2(4) . . . . ?
C3 N2 C11 N1 -0.3(3) . . . . ?
C3 N2 C11 C16 -178.3(3) . . . . ?
C2 N1 C11 N2 0.6(3) . . . . ?
C12 N1 C11 N2 -178.7(2) . . . . ?
C2 N1 C11 C16 178.5(3) . . . . ?
C12 N1 C11 C16 -0.8(4) . . . . ?
C2 N1 C12 C13 84.4(3) . . . . ?
C11 N1 C12 C13 -96.4(3) . . . . ?
N1 C12 C13 C14 -173.3(2) . . . . ?
C12 C13 C14 C15 69.5(4) . . . . ?
