#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025326.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_4025326
loop_
_publ_author_name
'Donald C. Rogness'
'Richard C. Larock'
_publ_section_title
;
 Synthesis of Acridines by the [4 + 2] Annulation of Arynes and
 2-Aminoaryl Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2289
_journal_page_last               2295
_journal_paper_doi               10.1021/jo1000687
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C24 H17 N'
_chemical_formula_weight         319.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 107.314(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.660(7)
_cell_length_b                   5.928(4)
_cell_length_c                   23.352(7)
_cell_measurement_reflns_used    908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      3.40
_cell_volume                     3259(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0449
_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)+(0.0736P)²+1.2517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                2297
_reflns_number_total             3316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1000687_si_001.cif
_cod_data_source_block           lar17
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4025326
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16061(7) -0.1777(3) 0.01287(7) 0.0254(4) Uani 1 1 d . . .
C2 C 0.16614(8) -0.3298(3) -0.03205(8) 0.0316(5) Uani 1 1 d . . .
H2 H 0.1949 -0.3055 -0.0509 0.038 Uiso 1 1 calc R . .
C3 C 0.13063(8) -0.5104(3) -0.04843(8) 0.0347(5) Uani 1 1 d . . .
H3 H 0.1357 -0.6142 -0.0774 0.042 Uiso 1 1 calc R . .
C4 C 0.08645(8) -0.5434(3) -0.02258(8) 0.0319(4) Uani 1 1 d . . .
H4 H 0.0613 -0.6673 -0.0349 0.038 Uiso 1 1 calc R . .
C5 C 0.07962(7) -0.3983(3) 0.02010(8) 0.0270(4) Uani 1 1 d . . .
H5 H 0.0489 -0.4204 0.0362 0.032 Uiso 1 1 calc R . .
C6 C 0.11762(7) -0.2140(3) 0.04106(7) 0.0227(4) Uani 1 1 d . . .
C7 C 0.11539(7) -0.0689(3) 0.08862(7) 0.0209(4) Uani 1 1 d . . .
C8 C 0.06576(7) -0.0906(3) 0.11222(7) 0.0208(4) Uani 1 1 d . . .
C9 C 0.05716(7) -0.2795(3) 0.14423(7) 0.0228(4) Uani 1 1 d . . .
H9 H 0.0834 -0.4011 0.1512 0.027 Uiso 1 1 calc R . .
C10 C 0.01095(7) -0.2910(3) 0.16589(7) 0.0253(4) Uani 1 1 d . . .
H10 H 0.0060 -0.4203 0.1879 0.030 Uiso 1 1 calc R . .
C11 C -0.07795(8) -0.1260(4) 0.18173(9) 0.0379(5) Uani 1 1 d . . .
H11A H -0.0688 -0.0389 0.2191 0.057 Uiso 1 1 calc R . .
H11B H -0.0853 -0.2832 0.1900 0.057 Uiso 1 1 calc R . .
H11C H -0.1118 -0.0621 0.1528 0.057 Uiso 1 1 calc R . .
C12 C -0.02877(7) -0.1164(3) 0.15617(7) 0.0252(4) Uani 1 1 d . . .
C13 C -0.02091(7) 0.0679(3) 0.12276(8) 0.0284(4) Uani 1 1 d . . .
H13 H -0.0479 0.1869 0.1147 0.034 Uiso 1 1 calc R . .
C14 C 0.02522(7) 0.0817(3) 0.10107(8) 0.0271(4) Uani 1 1 d . . .
H14 H 0.0295 0.2096 0.0783 0.033 Uiso 1 1 calc R . .
C15 C 0.15740(7) 0.0979(3) 0.10843(7) 0.0213(4) Uani 1 1 d . . .
C16 C 0.16474(7) 0.2440(3) 0.16137(7) 0.0209(4) Uani 1 1 d . . .
C17 C 0.14100(7) 0.1996(3) 0.20799(7) 0.0240(4) Uani 1 1 d . . .
H17 H 0.1189 0.0671 0.2063 0.029 Uiso 1 1 calc R . .
C18 C 0.14905(7) 0.3437(3) 0.25598(8) 0.0276(4) Uani 1 1 d . . .
H18 H 0.1325 0.3086 0.2868 0.033 Uiso 1 1 calc R . .
C19 C 0.18114(7) 0.5408(3) 0.26025(8) 0.0276(4) Uani 1 1 d . . .
H19 H 0.1852 0.6427 0.2927 0.033 Uiso 1 1 calc R . .
C20 C 0.20659(7) 0.5838(3) 0.21660(8) 0.0277(4) Uani 1 1 d . . .
H20 H 0.2288 0.7164 0.2193 0.033 Uiso 1 1 calc R . .
C21 C 0.20061(7) 0.4366(3) 0.16812(8) 0.0229(4) Uani 1 1 d . . .
C22 C 0.23279(7) 0.4742(3) 0.12692(8) 0.0262(4) Uani 1 1 d . . .
H22 H 0.2549 0.6076 0.1305 0.031 Uiso 1 1 calc R . .
C23 C 0.23235(7) 0.3256(3) 0.08361(8) 0.0271(4) Uani 1 1 d . . .
H23 H 0.2568 0.3480 0.0595 0.032 Uiso 1 1 calc R . .
C24 C 0.19514(7) 0.1313(3) 0.07300(7) 0.0233(4) Uani 1 1 d . . .
N1 N 0.19724(6) -0.0014(3) 0.02747(6) 0.0270(4) Uani 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'
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
N1 C1 C6 122.20(16) . . ?
N1 C1 C2 118.14(16) . . ?
C6 C1 C2 119.66(17) . . ?
C3 C2 C1 120.72(18) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.20(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.35(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.45(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 118.63(16) . . ?
C1 C6 C5 117.46(16) . . ?
C7 C6 C5 123.90(16) . . ?
C15 C7 C6 119.14(15) . . ?
C15 C7 C8 123.00(14) . . ?
C6 C7 C8 117.70(14) . . ?
C9 C8 C14 118.10(15) . . ?
C9 C8 C7 122.65(14) . . ?
C14 C8 C7 119.24(14) . . ?
C10 C9 C8 120.64(15) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C12 121.31(16) . . ?
C9 C10 H10 119.3 . . ?
C12 C10 H10 119.3 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 117.76(16) . . ?
C13 C12 C11 121.10(16) . . ?
C10 C12 C11 121.13(16) . . ?
C14 C13 C12 121.44(16) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C8 120.69(16) . . ?
C13 C14 H14 119.7 . . ?
C8 C14 H14 119.7 . . ?
C7 C15 C24 116.69(15) . . ?
C7 C15 C16 125.64(15) . . ?
C24 C15 C16 117.66(15) . . ?
C17 C16 C21 116.89(15) . . ?
C17 C16 C15 124.28(15) . . ?
C21 C16 C15 118.73(15) . . ?
C18 C17 C16 121.48(16) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.24(17) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 118.48(16) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 121.58(16) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C16 120.07(16) . . ?
C20 C21 C22 119.89(16) . . ?
C16 C21 C22 119.97(15) . . ?
C23 C22 C21 121.48(16) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 121.00(16) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
N1 C24 C15 124.36(16) . . ?
N1 C24 C23 115.60(15) . . ?
C15 C24 C23 119.97(15) . . ?
C24 N1 C1 118.24(14) . . ?
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
C1 N1 1.357(2) . ?
C1 C6 1.421(2) . ?
C1 C2 1.420(3) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.428(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(2) . ?
C7 C15 1.407(2) . ?
C7 C8 1.490(2) . ?
C8 C9 1.397(2) . ?
C8 C14 1.399(2) . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C12 1.397(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.504(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.389(3) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C24 1.431(2) . ?
C15 C16 1.476(2) . ?
C16 C17 1.406(2) . ?
C16 C21 1.424(2) . ?
C17 C18 1.376(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.402(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.435(2) . ?
C22 C23 1.339(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.447(2) . ?
C23 H23 0.9500 . ?
C24 N1 1.336(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659169
2 PubChem 46187960
