#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151082.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_7151082
loop_
_publ_author_name
'Cockroft, Scott L.'
'Perkins, Julie'
'Zonta, Cristiano'
'Adams, Harry'
'Spey, Sharon E.'
'Low, Caroline M. R.'
'Vinter, Jeremy G.'
'Lawson, Kevin R.'
'Urch, Christopher J.'
'Hunter, Christopher A.'
_publ_section_title
;
 Substituent effects on aromatic stacking interactions.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1062
_journal_page_last               1080
_journal_paper_doi               10.1039/b617576g
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C19 H24 N2 O'
_chemical_formula_weight         296.40
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.181(9)
_cell_length_b                   19.20(2)
_cell_length_c                   19.68(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.07
_cell_volume                     3469(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SIEMENS P4'
_diffrn_measurement_method       'ω 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  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3889
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.07
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0727
_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)+(0.0749P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1921
_reflns_number_gt                1423
_reflns_number_total             3059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b617576g.txt
_cod_data_source_block           och27a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to
'constr' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        3468(7)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7151082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O1 O 0.5633(3) 0.09603(13) 0.30081(12) 0.0573(7) Uani 1 1 d . . .
N1 N 0.3212(3) 0.10371(14) 0.28347(14) 0.0479(8) Uani 1 1 d . . .
H1 H 0.2500 0.0900 0.2584 0.057 Uiso 1 1 calc R . .
N2 N 0.1695(4) 0.28772(16) 0.49642(18) 0.0676(10) Uani 1 1 d . . .
C1 C 0.4542(4) 0.07936(18) 0.26861(18) 0.0452(9) Uani 1 1 d . . .
C2 C 0.2882(4) 0.15095(18) 0.33804(19) 0.0453(9) Uani 1 1 d . . .
C3 C 0.2524(4) 0.22081(18) 0.3231(2) 0.0509(10) Uani 1 1 d . . .
C4 C 0.2137(4) 0.26468(19) 0.3766(2) 0.0568(11) Uani 1 1 d . . .
H4 H 0.1907 0.3108 0.3667 0.068 Uiso 1 1 calc R . .
C5 C 0.2077(4) 0.24300(19) 0.4439(2) 0.0537(10) Uani 1 1 d . . .
C6 C 0.2447(4) 0.17250(19) 0.45639(19) 0.0538(10) Uani 1 1 d . . .
H6 H 0.2418 0.1560 0.5008 0.065 Uiso 1 1 calc R . .
C7 C 0.2850(4) 0.12733(17) 0.40505(19) 0.0455(9) Uani 1 1 d . . .
C8 C 0.4606(4) 0.02814(18) 0.21045(19) 0.0495(10) Uani 1 1 d . . .
C9 C 0.5009(5) -0.0417(2) 0.2244(2) 0.0666(12) Uani 1 1 d . . .
C10 C 0.5062(5) -0.0881(2) 0.1700(3) 0.0877(15) Uani 1 1 d . . .
H10 H 0.5311 -0.1343 0.1781 0.105 Uiso 1 1 calc R . .
C11 C 0.4758(6) -0.0675(3) 0.1052(3) 0.0875(16) Uani 1 1 d . . .
H11 H 0.4799 -0.0994 0.0697 0.105 Uiso 1 1 calc R . .
C12 C 0.4389(5) 0.0010(3) 0.0924(2) 0.0778(14) Uani 1 1 d . . .
H12 H 0.4189 0.0148 0.0481 0.093 Uiso 1 1 calc R . .
C13 C 0.4310(4) 0.0495(2) 0.1440(2) 0.0567(11) Uani 1 1 d . . .
C14 C 0.2523(5) 0.2475(2) 0.2518(2) 0.0768(13) Uani 1 1 d . . .
H14A H 0.2216 0.2953 0.2515 0.115 Uiso 1 1 calc R . .
H14B H 0.1864 0.2203 0.2248 0.115 Uiso 1 1 calc R . .
H14C H 0.3487 0.2441 0.2332 0.115 Uiso 1 1 calc R . .
C15 C 0.3209(4) 0.05200(17) 0.4217(2) 0.0642(12) Uani 1 1 d . . .
H15A H 0.2630 0.0217 0.3938 0.096 Uiso 1 1 calc R . .
H15B H 0.3001 0.0431 0.4687 0.096 Uiso 1 1 calc R . .
H15C H 0.4223 0.0435 0.4131 0.096 Uiso 1 1 calc R . .
C16 C 0.5369(6) -0.0650(2) 0.2953(2) 0.0948(17) Uani 1 1 d . . .
H16A H 0.5521 -0.1144 0.2956 0.142 Uiso 1 1 calc R . .
H16B H 0.4577 -0.0535 0.3251 0.142 Uiso 1 1 calc R . .
H16C H 0.6238 -0.0419 0.3104 0.142 Uiso 1 1 calc R . .
C17 C 0.3958(4) 0.1245(2) 0.1268(2) 0.0709(13) Uani 1 1 d . . .
H17A H 0.4083 0.1318 0.0789 0.106 Uiso 1 1 calc R . .
H17B H 0.4601 0.1548 0.1514 0.106 Uiso 1 1 calc R . .
H17C H 0.2969 0.1344 0.1392 0.106 Uiso 1 1 calc R . .
C18 C 0.1236(5) 0.2596(2) 0.5602(2) 0.0798(14) Uani 1 1 d . . .
H18A H 0.0408 0.2299 0.5532 0.120 Uiso 1 1 calc R . .
H18B H 0.0973 0.2969 0.5902 0.120 Uiso 1 1 calc R . .
H18C H 0.2016 0.2332 0.5799 0.120 Uiso 1 1 calc R . .
C19 C 0.1267(5) 0.3583(2) 0.4801(2) 0.0818(14) Uani 1 1 d . . .
H19A H 0.2018 0.3801 0.4537 0.123 Uiso 1 1 calc R . .
H19B H 0.1120 0.3841 0.5213 0.123 Uiso 1 1 calc R . .
H19C H 0.0378 0.3575 0.4544 0.123 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 125.1(3) . . ?
C5 N2 C18 119.6(3) . . ?
C5 N2 C19 118.8(4) . . ?
C18 N2 C19 117.9(3) . . ?
O1 C1 N1 122.7(3) . . ?
O1 C1 C8 121.9(3) . . ?
N1 C1 C8 115.4(3) . . ?
C7 C2 C3 120.0(3) . . ?
C7 C2 N1 120.4(3) . . ?
C3 C2 N1 119.5(3) . . ?
C4 C3 C2 118.4(4) . . ?
C4 C3 C14 120.1(3) . . ?
C2 C3 C14 121.4(3) . . ?
C3 C4 C5 123.3(4) . . ?
N2 C5 C4 122.3(4) . . ?
N2 C5 C6 121.4(4) . . ?
C4 C5 C6 116.3(4) . . ?
C7 C6 C5 122.4(4) . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 C15 119.8(4) . . ?
C2 C7 C15 120.6(3) . . ?
C13 C8 C9 120.7(4) . . ?
C13 C8 C1 120.7(3) . . ?
C9 C8 C1 118.6(4) . . ?
C10 C9 C8 117.7(4) . . ?
C10 C9 C16 121.0(4) . . ?
C8 C9 C16 121.3(4) . . ?
C11 C10 C9 121.7(5) . . ?
C10 C11 C12 119.7(5) . . ?
C13 C12 C11 121.5(5) . . ?
C12 C13 C8 118.7(4) . . ?
C12 C13 C17 119.2(4) . . ?
C8 C13 C17 122.0(4) . . ?
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 1.228(4) . ?
N1 C1 1.340(4) . ?
N1 C2 1.438(4) . ?
N2 C5 1.389(5) . ?
N2 C18 1.429(5) . ?
N2 C19 1.447(5) . ?
C1 C8 1.510(5) . ?
C2 C7 1.395(5) . ?
C2 C3 1.412(5) . ?
C3 C4 1.394(5) . ?
C3 C14 1.494(5) . ?
C4 C5 1.390(5) . ?
C5 C6 1.417(5) . ?
C6 C7 1.382(5) . ?
C7 C15 1.519(5) . ?
C8 C13 1.397(5) . ?
C8 C9 1.417(5) . ?
C9 C10 1.394(6) . ?
C9 C16 1.501(6) . ?
C10 C11 1.365(6) . ?
C11 C12 1.381(6) . ?
C12 C13 1.379(5) . ?
C13 C17 1.513(6) . ?
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
C2 N1 C1 O1 -0.6(5) . . . . ?
C2 N1 C1 C8 177.8(3) . . . . ?
C1 N1 C2 C7 -75.4(5) . . . . ?
C1 N1 C2 C3 107.6(4) . . . . ?
C7 C2 C3 C4 -0.2(5) . . . . ?
N1 C2 C3 C4 176.8(3) . . . . ?
C7 C2 C3 C14 -178.9(3) . . . . ?
N1 C2 C3 C14 -1.9(5) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C14 C3 C4 C5 178.3(4) . . . . ?
C18 N2 C5 C4 161.6(4) . . . . ?
C19 N2 C5 C4 3.5(6) . . . . ?
C18 N2 C5 C6 -19.2(6) . . . . ?
C19 N2 C5 C6 -177.3(4) . . . . ?
C3 C4 C5 N2 179.7(4) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
N2 C5 C6 C7 -179.1(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 -0.8(5) . . . . ?
C5 C6 C7 C15 -179.0(3) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
N1 C2 C7 C6 -176.2(3) . . . . ?
C3 C2 C7 C15 179.0(3) . . . . ?
N1 C2 C7 C15 2.0(5) . . . . ?
O1 C1 C8 C13 -113.9(4) . . . . ?
N1 C1 C8 C13 67.8(4) . . . . ?
O1 C1 C8 C9 64.6(5) . . . . ?
N1 C1 C8 C9 -113.8(4) . . . . ?
C13 C8 C9 C10 -1.5(6) . . . . ?
C1 C8 C9 C10 -180.0(4) . . . . ?
C13 C8 C9 C16 178.4(4) . . . . ?
C1 C8 C9 C16 -0.1(6) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C16 C9 C10 C11 -179.0(5) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C10 C11 C12 C13 -0.4(7) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
C11 C12 C13 C17 177.6(4) . . . . ?
C9 C8 C13 C12 1.3(6) . . . . ?
C1 C8 C13 C12 179.7(3) . . . . ?
C9 C8 C13 C17 -176.5(4) . . . . ?
C1 C8 C13 C17 1.9(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17274013
2 PubChem 16116793
