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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/71/7217131.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_7217131
loop_
_publ_author_name
'Mercadal, Nerea'
'Day, Stephen P.'
'Jarmyn, Andrew'
'Pitak, Mateusz B.'
'Coles, Simon J.'
'Wilson, Claire'
'Rees, Gregory J.'
'Hanna, John V.'
'Wallis, John D.'
_publ_section_title
;
 O- vs. N-protonation of 1-dimethylaminonaphthalene-8-ketones: formation
 of a peri N--C bond or a hydrogen bond to the pi-electron density of a
 carbonyl group
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              8363
_journal_paper_doi               10.1039/C4CE00981A
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.34
_chemical_name_systematic
; 
8-Benzoyl-1-dimethylaminonaphthalene, 10
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.512(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0485(4)
_cell_length_b                   11.9670(5)
_cell_length_c                   14.4409(6)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.9496
_cell_measurement_theta_min      2.9047
_cell_volume                     1491.24(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7562
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3636
_exptl_crystal_size_mid          0.2752
_exptl_crystal_size_min          0.0691
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2641
_reflns_number_total             3429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00981a2.cif
_cod_data_source_block           ketone10
_cod_depositor_comments
'Adding full bibliography for 7217128--7217139.cif.'
_cod_original_cell_volume        1491.24(11)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7217131
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.91709(13) 0.10109(9) 0.09980(9) 0.0399(3) Uani 1 1 d .
N1 N 1.16929(14) 0.24818(11) 0.24316(9) 0.0288(3) Uani 1 1 d .
C1 C 1.08873(17) 0.33748(12) 0.27236(11) 0.0261(3) Uani 1 1 d .
C2 C 1.1545(2) 0.40676(15) 0.34919(12) 0.0399(4) Uani 1 1 d .
H2 H 1.2611 0.3986 0.3845 0.048 Uiso 1 1 calc R
C3 C 1.0660(2) 0.48963(15) 0.37624(14) 0.0484(5) Uani 1 1 d .
H3 H 1.1137 0.5378 0.4291 0.058 Uiso 1 1 calc R
C4 C 0.9135(2) 0.50198(14) 0.32815(13) 0.0432(5) Uani 1 1 d .
H4 H 0.8549 0.5574 0.3486 0.052 Uiso 1 1 calc R
C5 C 0.84041(19) 0.43305(12) 0.24757(12) 0.0311(4) Uani 1 1 d .
C6 C 0.6814(2) 0.44178(15) 0.19756(14) 0.0404(4) Uani 1 1 d .
H6 H 0.6202 0.4950 0.2183 0.049 Uiso 1 1 calc R
C7 C 0.61388(19) 0.37542(17) 0.12010(13) 0.0436(5) Uani 1 1 d .
H7 H 0.5061 0.3819 0.0876 0.052 Uiso 1 1 calc R
C8 C 0.70318(18) 0.29730(14) 0.08805(12) 0.0341(4) Uani 1 1 d .
H8 H 0.6554 0.2522 0.0330 0.041 Uiso 1 1 calc R
C9 C 0.85868(16) 0.28494(12) 0.13492(10) 0.0246(3) Uani 1 1 d .
C10 C 0.93029(16) 0.35114(12) 0.21790(10) 0.0237(3) Uani 1 1 d .
C11 C 1.1712(2) 0.14613(15) 0.29857(13) 0.0468(5) Uani 1 1 d .
H11A H 1.2403 0.1560 0.3648 0.070 Uiso 1 1 calc R
H11B H 1.2084 0.0840 0.2674 0.070 Uiso 1 1 calc R
H11C H 1.0662 0.1298 0.3007 0.070 Uiso 1 1 calc R
C12 C 1.32355(18) 0.27665(17) 0.23733(14) 0.0464(5) Uani 1 1 d .
H12A H 1.3182 0.3468 0.2015 0.070 Uiso 1 1 calc R
H12B H 1.3606 0.2168 0.2036 0.070 Uiso 1 1 calc R
H12C H 1.3952 0.2854 0.3030 0.070 Uiso 1 1 calc R
C13 C 0.94504(17) 0.20019(12) 0.09438(10) 0.0259(3) Uani 1 1 d .
C14 C 1.04320(16) 0.23907(12) 0.03393(10) 0.0238(3) Uani 1 1 d .
C15 C 1.06809(17) 0.35178(13) 0.02009(12) 0.0309(4) Uani 1 1 d .
H15 H 1.0222 0.4071 0.0499 0.037 Uiso 1 1 calc R
C16 C 1.15948(19) 0.38357(14) -0.03695(13) 0.0387(4) Uani 1 1 d .
H16 H 1.1765 0.4606 -0.0460 0.046 Uiso 1 1 calc R
C17 C 1.22580(19) 0.30393(15) -0.08063(12) 0.0409(4) Uani 1 1 d .
H17 H 1.2880 0.3259 -0.1200 0.049 Uiso 1 1 calc R
C18 C 1.20182(19) 0.19229(15) -0.06711(12) 0.0378(4) Uani 1 1 d .
H18 H 1.2482 0.1373 -0.0969 0.045 Uiso 1 1 calc R
C19 C 1.11059(18) 0.15988(13) -0.01041(11) 0.0304(4) Uani 1 1 d .
H19 H 1.0940 0.0827 -0.0018 0.036 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
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
C1 N1 C11 112.84(12)
C1 N1 C12 115.06(13)
C12 N1 C11 111.88(14)
C2 C1 C10 119.91(14)
C2 C1 N1 123.82(14)
C10 C1 N1 116.26(12)
C1 C2 C3 120.54(17)
C4 C3 C2 120.94(16)
C3 C4 C5 120.65(16)
C6 C5 C4 122.08(15)
C6 C5 C10 119.13(15)
C4 C5 C10 118.77(15)
C7 C6 C5 121.12(15)
C6 C7 C8 120.05(16)
C9 C8 C7 121.04(16)
C8 C9 C10 119.70(14)
C8 C9 C13 117.16(13)
C10 C9 C13 123.14(13)
C5 C10 C9 118.85(14)
C5 C10 C1 119.09(13)
C9 C10 C1 122.05(13)
O1 C13 C14 120.74(14)
O1 C13 C9 119.28(13)
C14 C13 C9 119.18(12)
C19 C14 C15 118.98(14)
C19 C14 C13 118.63(13)
C15 C14 C13 122.40(13)
C16 C15 C14 120.21(14)
C17 C16 C15 120.21(16)
C16 C17 C18 119.86(15)
C17 C18 C19 120.27(15)
C18 C19 C14 120.47(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.2200(17)
N1 C1 1.4269(19)
N1 C11 1.457(2)
N1 C12 1.4637(19)
C1 C2 1.369(2)
C1 C10 1.422(2)
C2 C3 1.402(2)
C3 C4 1.353(3)
C4 C5 1.417(2)
C5 C6 1.406(2)
C5 C10 1.420(2)
C6 C7 1.358(3)
C7 C8 1.402(2)
C8 C9 1.374(2)
C9 C10 1.420(2)
C9 C13 1.502(2)
C13 C14 1.495(2)
C14 C19 1.384(2)
C14 C15 1.392(2)
C15 C16 1.385(2)
C16 C17 1.376(2)
C17 C18 1.377(2)
C18 C19 1.382(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198895
