#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/87/1548726.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_1548726
loop_
_publ_author_name
'Ait Elhad, Mustapha'
'Benharref, Ahmed'
'El Ammari, Lahcen'
'Saadi, Mohamed'
'Mazoir, Noureddine'
'Berraho, Moha'
_publ_section_title
;
 1-(2-Isopropyl-4,7-dimethyl-3-nitronaphthalen-1-yl)ethanone
;
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x180083
_journal_paper_doi               10.1107/S2414314618000834
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C17 H19 N O3'
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_name_systematic
;
1-(-2-Isopropyl-4,7-dimethyl-3-nitronaphthalen-1-yl)ethanone
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.172(7)
_cell_length_b                   8.532(5)
_cell_length_c                   16.287(14)
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.6
_cell_volume                     1488.2(18)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014/7 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53166
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.594
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.246
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0605P)²+0.6136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                2710
_reflns_number_total             3039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bx4010sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1488.3(18)
_cod_database_code               1548726
_cod_database_fobs_code          1548726
_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   0.957
_shelx_estimated_absorpt_t_max   0.987
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 -0.10207(11) 0.94498(15) 0.28104(8) 0.0265(3) Uani d 1
C C2 -0.06720(11) 0.81421(15) 0.33627(8) 0.0248(3) Uani d 1
C C3 -0.09475(12) 0.81565(16) 0.41605(8) 0.0293(3) Uani d 1
H H3 -0.0714 0.7283 0.4533 0.035 Uiso calc 1
C C4 -0.15427(12) 0.93988(17) 0.44081(9) 0.0328(3) Uani d 1
C C5 -0.18796(14) 1.06889(18) 0.38536(10) 0.0379(3) Uani d 1
H H5 -0.2291 1.1556 0.4020 0.045 Uiso calc 1
C C6 -0.16279(13) 1.07237(17) 0.30799(10) 0.0350(3) Uani d 1
H H6 -0.1863 1.1613 0.2719 0.042 Uiso calc 1
C C7 -0.07567(12) 0.94410(15) 0.20035(8) 0.0275(3) Uani d 1
C C8 -0.01491(11) 0.81585(15) 0.18140(8) 0.0255(3) Uani d 1
C C9 0.02572(11) 0.68362(15) 0.23498(8) 0.0253(3) Uani d 1
C C10 -0.00404(11) 0.68558(15) 0.31139(8) 0.0251(3) Uani d 1
C C11 0.02958(14) 0.54943(16) 0.37334(9) 0.0321(3) Uani d 1
C C12 0.10052(13) 0.54700(16) 0.21429(9) 0.0310(3) Uani d 1
H H12 0.0992 0.4634 0.2570 0.037 Uiso calc 1
C C13 0.04528(15) 0.47259(18) 0.12646(10) 0.0397(4) Uani d 1
H H13A -0.0442 0.4544 0.1172 0.060 Uiso calc 1
H H13B 0.0871 0.3725 0.1238 0.060 Uiso calc 1
H H13C 0.0575 0.5430 0.0820 0.060 Uiso calc 1
C C14 0.23845(14) 0.5897(2) 0.22909(10) 0.0430(4) Uani d 1
H H14A 0.2454 0.6733 0.1894 0.064 Uiso calc 1
H H14B 0.2845 0.4972 0.2191 0.064 Uiso calc 1
H H14C 0.2736 0.6259 0.2882 0.064 Uiso calc 1
C C15 0.15202(16) 0.5564(2) 0.43893(10) 0.0463(4) Uani d 1
H H15A 0.1455 0.6226 0.4866 0.069 Uiso calc 1
H H15B 0.2143 0.6006 0.4136 0.069 Uiso calc 1
H H15C 0.1775 0.4504 0.4601 0.069 Uiso calc 1
C C16 -0.18325(16) 0.9376(2) 0.52558(11) 0.0439(4) Uani d 1
H H16A -0.2550 0.8690 0.5216 0.066 Uiso calc 1
H H16B -0.2029 1.0441 0.5403 0.066 Uiso calc 1
H H16C -0.1107 0.8982 0.5700 0.066 Uiso calc 1
C C17 -0.11145(16) 1.08268(18) 0.14152(10) 0.0420(4) Uani d 1
H H17A -0.0784 1.0689 0.0923 0.063 Uiso calc 1
H H17B -0.0766 1.1784 0.1724 0.063 Uiso calc 1
H H17C -0.2026 1.0911 0.1214 0.063 Uiso calc 1
O O1 0.11116(11) 0.85261(15) 0.09187(7) 0.0492(3) Uani d 1
O O2 -0.08085(11) 0.78675(15) 0.03444(6) 0.0472(3) Uani d 1
O O3 -0.04474(13) 0.44427(14) 0.37083(8) 0.0550(4) Uani d 1
N N 0.00735(11) 0.81813(14) 0.09622(7) 0.0323(3) Uani d 1
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 118.51(13)
C6 C1 C7 122.20(12)
C2 C1 C7 119.30(12)
C1 C2 C3 118.88(12)
C1 C2 C10 119.67(12)
C3 C2 C10 121.44(12)
C4 C3 C2 121.74(13)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 118.68(14)
C3 C4 C16 120.57(14)
C5 C4 C16 120.75(14)
C6 C5 C4 121.43(13)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 120.77(14)
C5 C6 H6 119.6
C1 C6 H6 119.6
C8 C7 C1 117.25(12)
C8 C7 C17 122.99(13)
C1 C7 C17 119.74(12)
C7 C8 C9 126.10(12)
C7 C8 N 115.34(11)
C9 C8 N 118.55(12)
C10 C9 C8 115.40(12)
C10 C9 C12 119.80(11)
C8 C9 C12 124.78(12)
C9 C10 C2 122.22(12)
C9 C10 C11 121.01(12)
C2 C10 C11 116.77(12)
O3 C11 C15 122.47(14)
O3 C11 C10 120.43(14)
C15 C11 C10 117.00(13)
C13 C12 C9 115.08(12)
C13 C12 C14 111.48(12)
C9 C12 C14 111.86(12)
C13 C12 H12 105.9
C9 C12 H12 105.9
C14 C12 H12 105.9
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
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C11 C15 H15A 109.5
C11 C15 H15B 109.5
H15A C15 H15B 109.5
C11 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 C16 H16A 109.5
C4 C16 H16B 109.5
H16A C16 H16B 109.5
C4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C7 C17 H17A 109.5
C7 C17 H17B 109.5
H17A C17 H17B 109.5
C7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O1 N O2 124.29(13)
O1 N C8 118.38(12)
O2 N C8 117.32(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.4156(19)
C1 C2 1.4165(19)
C1 C7 1.426(2)
C2 C3 1.418(2)
C2 C10 1.4246(19)
C3 C4 1.372(2)
C3 H3 0.9500
C4 C5 1.405(2)
C4 C16 1.505(2)
C5 C6 1.367(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.3685(19)
C7 C17 1.503(2)
C8 C9 1.4195(19)
C8 N 1.478(2)
C9 C10 1.377(2)
C9 C12 1.5268(19)
C10 C11 1.514(2)
C11 O3 1.2152(19)
C11 C15 1.478(2)
C12 C13 1.526(2)
C12 C14 1.534(2)
C12 H12 1.0000
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
O1 N 1.2180(18)
O2 N 1.2210(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H14A O1 . 0.98 2.40 3.200(3) 139
C16 H16C Cg 3_665 0.98 2.92 3.591(4) 127
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139051743
