#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/48/7114814.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_7114814
loop_
_publ_author_name
'Adams, Harry'
'Bernad Jr., Pablo L.'
'Hembury, Guy A.'
'Hunter, Christopher A.'
'McCabe, James F.'
'Eggleston, Drake S.'
'Haltiwanger, R. Curtis'
'Livingstone, David J.'
'D. M. Harris, Kenneth'
'Kariuki, Benson M.'
_publ_section_title
;
 Substituent effects on aromatic interactions in the solid state
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1500
_journal_paper_doi               10.1039/b101575n
_journal_year                    2001
_chemical_formula_sum            'C25 H36 N2 O'
_chemical_formula_weight         380.56
_chemical_name_common
'N-4 dimethylamino 2,6 diisopropylphenyl 4 t-butylbenzamide'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.911(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.539(2)
_cell_length_b                   10.092(2)
_cell_length_c                   25.400(5)
_cell_measurement_temperature    296(2)
_cell_volume                     2408.7(8)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       'Rigaku R-Axis'
_diffrn_measurement_method       'Image plate scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.2402
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9063
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.063
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_F_000             832
_exptl_crystal_size_max          1.80
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.725
_refine_ls_goodness_of_fit_obs   1.156
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.725
_refine_ls_restrained_S_obs      1.156
_refine_ls_R_factor_all          0.1979
_refine_ls_R_factor_obs          0.0690
_refine_ls_shift/esd_max         0.054
_refine_ls_shift/esd_mean        0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0759P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1996
_refine_ls_wR_factor_obs         0.1677
_reflns_number_observed          1158
_reflns_number_total             3663
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b101575n.txt
_cod_data_source_block           gah17
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7114814
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2571(4) 0.3415(3) 0.75460(13) 0.0865(13) Uani 1 d .
N1 N -0.1463(5) 0.1567(5) 0.5407(2) 0.093(2) Uani 1 d .
N2 N 0.2082(4) 0.1260(3) 0.74126(13) 0.0532(11) Uani 1 d .
H2 H 0.2165(4) 0.0479(3) 0.75501(13) 0.064 Uiso 1 calc R
C1 C -0.0593(5) 0.1545(4) 0.5905(2) 0.0576(13) Uani 1 d .
C2 C -0.1156(5) 0.1511(4) 0.6375(2) 0.0584(13) Uani 1 d .
H2A H -0.2139(5) 0.1524(4) 0.6352(2) 0.070 Uiso 1 calc R
C3 C -0.0297(5) 0.1460(4) 0.6878(2) 0.0524(12) Uani 1 d .
C4 C 0.1176(5) 0.1442(4) 0.6908(2) 0.0465(12) Uani 1 d .
C5 C 0.1773(5) 0.1490(4) 0.6447(2) 0.0545(13) Uani 1 d .
C6 C 0.0886(5) 0.1560(4) 0.5949(2) 0.0641(14) Uani 1 d .
H6 H 0.1289(5) 0.1619(4) 0.5641(2) 0.077 Uiso 1 calc R
C7 C -0.0890(6) 0.1785(5) 0.4926(2) 0.089(2) Uani 1 d .
H7A H -0.1647(6) 0.1767(5) 0.4624(2) 0.107 Uiso 1 calc R
H7B H -0.0214(6) 0.1101(5) 0.4889(2) 0.107 Uiso 1 calc R
H7C H -0.0426(6) 0.2632(5) 0.4945(2) 0.107 Uiso 1 calc R
C8 C -0.2966(5) 0.1342(5) 0.5365(2) 0.090(2) Uani 1 d .
H8A H -0.3412(5) 0.1390(5) 0.4996(2) 0.107 Uiso 1 calc R
H8B H -0.3367(5) 0.2005(5) 0.5566(2) 0.107 Uiso 1 calc R
H8C H -0.3124(5) 0.0480(5) 0.5504(2) 0.107 Uiso 1 calc R
C9 C -0.0921(6) 0.1441(6) 0.7378(2) 0.080(2) Uani 1 d .
H9 H -0.0209(6) 0.1011(6) 0.7648(2) 0.096 Uiso 1 calc R
C12 C 0.3368(5) 0.1457(6) 0.6466(2) 0.075(2) Uani 1 d .
H12 H 0.3799(5) 0.1369(6) 0.6843(2) 0.090 Uiso 1 calc R
C13 C 0.3832(6) 0.0265(7) 0.6186(3) 0.140(3) Uani 1 d .
H13A H 0.3451(6) -0.0521(7) 0.6320(3) 0.168 Uiso 1 calc R
H13B H 0.4852(6) 0.0217(7) 0.6249(3) 0.168 Uiso 1 calc R
H13C H 0.3489(6) 0.0338(7) 0.5809(3) 0.168 Uiso 1 calc R
C14 C 0.3927(6) 0.2726(6) 0.6274(3) 0.125(3) Uani 1 d .
H14A H 0.3606(6) 0.3458(6) 0.6464(3) 0.150 Uiso 1 calc R
H14B H 0.3584(6) 0.2827(6) 0.5898(3) 0.150 Uiso 1 calc R
H14C H 0.4948(6) 0.2705(6) 0.6339(3) 0.150 Uiso 1 calc R
C15 C 0.2810(5) 0.2262(4) 0.7680(2) 0.0558(14) Uani 1 d .
C16 C 0.3953(5) 0.1913(4) 0.8137(2) 0.0519(13) Uani 1 d .
C17 C 0.4748(5) 0.2915(4) 0.8405(2) 0.067(2) Uani 1 d .
H17 H 0.4490(5) 0.3790(4) 0.8324(2) 0.080 Uiso 1 calc R
C18 C 0.5915(5) 0.2659(4) 0.8791(2) 0.067(2) Uani 1 d .
H18 H 0.6438(5) 0.3366(4) 0.8958(2) 0.080 Uiso 1 calc R
C19 C 0.6330(5) 0.1397(4) 0.8936(2) 0.0616(14) Uani 1 d .
C20 C 0.5501(6) 0.0391(4) 0.8679(2) 0.089(2) Uani 1 d .
H20 H 0.5735(6) -0.0481(4) 0.8775(2) 0.106 Uiso 1 calc R
C21 C 0.4337(5) 0.0627(4) 0.8286(2) 0.078(2) Uani 1 d .
H21 H 0.3809(5) -0.0080(4) 0.8122(2) 0.094 Uiso 1 calc R
C22 C 0.7668(6) 0.1082(5) 0.9345(2) 0.085(2) Uani 1 d .
C23 C 0.8621(7) 0.0198(7) 0.9103(3) 0.155(3) Uani 1 d .
H23A H 0.8092(7) -0.0555(7) 0.8946(3) 0.186 Uiso 1 calc R
H23B H 0.9385(7) -0.0097(7) 0.9375(3) 0.186 Uiso 1 calc R
H23C H 0.9004(7) 0.0672(7) 0.8833(3) 0.186 Uiso 1 calc R
C24 C 0.8381(6) 0.2290(5) 0.9603(3) 0.127(3) Uani 1 d .
H24A H 0.7702(6) 0.2812(5) 0.9750(3) 0.153 Uiso 1 calc R
H24B H 0.8760(6) 0.2802(5) 0.9341(3) 0.153 Uiso 1 calc R
H24C H 0.9140(6) 0.2032(5) 0.9883(3) 0.153 Uiso 1 calc R
C25 C 0.7185(7) 0.0270(6) 0.9820(3) 0.136(3) Uani 1 d .
H25A H 0.6562(7) 0.0807(6) 0.9990(3) 0.163 Uiso 1 calc R
H25B H 0.8009(7) 0.0034(6) 1.0077(3) 0.163 Uiso 1 calc R
H25C H 0.6695(7) -0.0519(6) 0.9681(3) 0.163 Uiso 1 calc R
C26 C -0.2138(16) 0.0782(15) 0.7381(4) 0.423(14) Uani 1 d .
H26A H -0.2062(16) -0.0094(15) 0.7242(4) 0.507 Uiso 1 calc R
H26B H -0.2908(16) 0.1243(15) 0.7164(4) 0.507 Uiso 1 calc R
H26C H -0.2318(16) 0.0725(15) 0.7741(4) 0.507 Uiso 1 calc R
C27 C -0.1166(15) 0.2716(10) 0.7590(5) 0.336(10) Uani 1 d .
H27A H -0.0329(15) 0.3252(10) 0.7606(5) 0.404 Uiso 1 calc R
H27B H -0.1384(15) 0.2615(10) 0.7944(5) 0.404 Uiso 1 calc R
H27C H -0.1951(15) 0.3136(10) 0.7365(5) 0.404 Uiso 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 C7 121.4(5)
C1 N1 C8 119.8(5)
C7 N1 C8 118.8(4)
C15 N2 C4 122.5(3)
N1 C1 C2 121.6(5)
N1 C1 C6 120.6(5)
C2 C1 C6 117.8(4)
C1 C2 C3 122.3(4)
C4 C3 C2 118.6(5)
C4 C3 C9 119.9(4)
C2 C3 C9 121.5(5)
C5 C4 C3 120.5(4)
C5 C4 N2 119.3(4)
C3 C4 N2 120.0(4)
C4 C5 C6 119.6(4)
C4 C5 C12 121.9(4)
C6 C5 C12 118.5(5)
C1 C6 C5 121.1(5)
C26 C9 C27 104.2(9)
C26 C9 C3 119.1(6)
C27 C9 C3 115.2(6)
C14 C12 C13 112.4(6)
C14 C12 C5 112.5(5)
C13 C12 C5 112.3(4)
O1 C15 N2 121.3(4)
O1 C15 C16 121.2(4)
N2 C15 C16 117.4(3)
C17 C16 C21 117.2(4)
C17 C16 C15 118.7(3)
C21 C16 C15 124.0(3)
C16 C17 C18 121.7(4)
C19 C18 C17 121.9(4)
C18 C19 C20 116.3(4)
C18 C19 C22 123.0(4)
C20 C19 C22 120.7(4)
C19 C20 C21 122.6(4)
C20 C21 C16 120.2(4)
C23 C22 C24 114.1(6)
C23 C22 C19 110.1(5)
C24 C22 C19 113.1(4)
C23 C22 C25 106.4(5)
C24 C22 C25 104.8(5)
C19 C22 C25 107.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.223(4)
N1 C1 1.388(6)
N1 C7 1.437(6)
N1 C8 1.438(6)
N2 C15 1.343(5)
N2 C4 1.428(5)
C1 C2 1.391(6)
C1 C6 1.396(6)
C2 C3 1.396(6)
C3 C4 1.394(6)
C3 C9 1.492(7)
C4 C5 1.389(6)
C5 C6 1.398(6)
C5 C12 1.515(6)
C9 C26 1.340(10)
C9 C27 1.430(9)
C12 C14 1.500(7)
C12 C13 1.502(7)
C15 C16 1.490(5)
C16 C17 1.373(5)
C16 C21 1.384(5)
C17 C18 1.375(5)
C18 C19 1.366(5)
C19 C20 1.380(6)
C19 C22 1.534(6)
C20 C21 1.380(6)
C22 C23 1.480(8)
C22 C24 1.491(6)
C22 C25 1.592(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5231238
