#------------------------------------------------------------------------------
#$Date: 2023-04-07 11:11:51 +0300 (Fri, 07 Apr 2023) $
#$Revision: 282517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107073.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_8107073
loop_
_publ_author_name
'Li, Yaping'
'Sun, Dajun'
'Ming, Julia'
'Su, Guanfang'
_publ_section_title
;
 Crystal structure of dimethyl 5-(dibenzylamino)isophthalate, C24H23NO4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              989
_journal_page_last               990
_journal_paper_doi               10.1515/ncrs-2016-0043
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C24 H23 N O4'
_chemical_formula_sum            'C24 H23 N O4'
_chemical_formula_weight         389.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.009(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.492(6)
_cell_length_b                   9.259(4)
_cell_length_c                   15.993(8)
_cell_measurement_reflns_used    4073
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.79
_cell_measurement_theta_min      1.69
_cell_volume                     1993.0(16)
_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, 2008) [8]'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10556
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0093(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.3136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2639
_reflns_number_total             4037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0043_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               8107073
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05525(13) -0.1785(2) -0.06012(11) 0.0562(5) Uani 1 1 d . . .
H1A H 0.0078 -0.2165 -0.1029 0.067 Uiso 1 1 calc R . .
H1B H 0.0295 -0.0871 -0.0415 0.067 Uiso 1 1 calc R . .
C2 C 0.06177(13) -0.28157(18) 0.01288(10) 0.0483(4) Uani 1 1 d . . .
C3 C 0.13981(15) -0.3746(2) 0.02618(12) 0.0615(5) Uani 1 1 d . . .
H3 H 0.1916 -0.3717 -0.0092 0.074 Uiso 1 1 calc R . .
C4 C 0.14317(17) -0.4725(2) 0.09099(13) 0.0732(6) Uani 1 1 d . . .
H4 H 0.1968 -0.5353 0.0988 0.088 Uiso 1 1 calc R . .
C5 C 0.06814(17) -0.4779(2) 0.14378(12) 0.0687(6) Uani 1 1 d . . .
H5 H 0.0705 -0.5437 0.1878 0.082 Uiso 1 1 calc R . .
C6 C -0.01012(17) -0.3863(3) 0.13148(13) 0.0749(6) Uani 1 1 d . . .
H6 H -0.0617 -0.3896 0.1671 0.090 Uiso 1 1 calc R . .
C7 C -0.01338(15) -0.2884(2) 0.06654(13) 0.0685(6) Uani 1 1 d . . .
H7 H -0.0672 -0.2259 0.0589 0.082 Uiso 1 1 calc R . .
C8 C 0.16092(15) -0.2091(2) -0.18044(10) 0.0580(5) Uani 1 1 d . . .
H8A H 0.1148 -0.2886 -0.1908 0.070 Uiso 1 1 calc R . .
H8B H 0.2276 -0.2480 -0.1812 0.070 Uiso 1 1 calc R . .
C9 C 0.14514(13) -0.1015(2) -0.25111(10) 0.0515(4) Uani 1 1 d . . .
C10 C 0.18728(16) -0.1264(2) -0.32525(12) 0.0680(6) Uani 1 1 d . . .
H10 H 0.2294 -0.2051 -0.3299 0.082 Uiso 1 1 calc R . .
C11 C 0.1680(2) -0.0363(3) -0.39290(13) 0.0875(8) Uani 1 1 d . . .
H11 H 0.1958 -0.0560 -0.4433 0.105 Uiso 1 1 calc R . .
C12 C 0.1085(2) 0.0815(3) -0.38650(14) 0.0863(8) Uani 1 1 d . . .
H12 H 0.0954 0.1420 -0.4324 0.104 Uiso 1 1 calc R . .
C13 C 0.06851(16) 0.1099(3) -0.31302(14) 0.0805(7) Uani 1 1 d . . .
H13 H 0.0292 0.1915 -0.3080 0.097 Uiso 1 1 calc R . .
C14 C 0.08589(15) 0.0185(2) -0.24575(12) 0.0691(6) Uani 1 1 d . . .
H14 H 0.0571 0.0382 -0.1958 0.083 Uiso 1 1 calc R . .
C15 C 0.21798(13) -0.06017(17) -0.05978(10) 0.0446(4) Uani 1 1 d . . .
C16 C 0.20603(12) 0.00105(17) 0.01858(10) 0.0456(4) Uani 1 1 d . . .
H16 H 0.1503 -0.0225 0.0469 0.055 Uiso 1 1 calc R . .
C17 C 0.27545(12) 0.09607(17) 0.05507(9) 0.0429(4) Uani 1 1 d . . .
C18 C 0.36014(12) 0.13144(18) 0.01569(9) 0.0461(4) Uani 1 1 d . . .
H18 H 0.4069 0.1949 0.0405 0.055 Uiso 1 1 calc R . .
C19 C 0.37354(12) 0.07000(18) -0.06150(10) 0.0452(4) Uani 1 1 d . . .
C20 C 0.30450(13) -0.02349(18) -0.09831(10) 0.0476(4) Uani 1 1 d . . .
H20 H 0.3155 -0.0634 -0.1502 0.057 Uiso 1 1 calc R . .
C21 C 0.25400(13) 0.16115(18) 0.13664(10) 0.0467(4) Uani 1 1 d . . .
C22 C 0.45971(13) 0.1075(2) -0.11017(10) 0.0511(4) Uani 1 1 d . . .
C23 C 0.30982(16) 0.3226(2) 0.24368(11) 0.0694(6) Uani 1 1 d . . .
H23A H 0.3653 0.3848 0.2583 0.104 Uiso 1 1 calc R . .
H23B H 0.3043 0.2518 0.2869 0.104 Uiso 1 1 calc R . .
H23C H 0.2500 0.3790 0.2379 0.104 Uiso 1 1 calc R . .
C24 C 0.59744(14) 0.2593(3) -0.11894(13) 0.0776(6) Uani 1 1 d . . .
H24A H 0.6405 0.1803 -0.1305 0.116 Uiso 1 1 calc R . .
H24B H 0.6343 0.3310 -0.0865 0.116 Uiso 1 1 calc R . .
H24C H 0.5712 0.3012 -0.1708 0.116 Uiso 1 1 calc R . .
N1 N 0.14804(11) -0.15165(15) -0.09763(8) 0.0528(4) Uani 1 1 d . . .
O1 O 0.18006(10) 0.13789(15) 0.17213(8) 0.0672(4) Uani 1 1 d . . .
O2 O 0.32461(9) 0.25123(14) 0.16560(7) 0.0608(4) Uani 1 1 d . . .
O3 O 0.47438(11) 0.05655(17) -0.17674(8) 0.0777(4) Uani 1 1 d . . .
O4 O 0.51747(9) 0.20784(15) -0.07289(7) 0.0600(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'
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
N1 C1 C2 115.16(15) . .
N1 C1 H1A 108.5 . .
C2 C1 H1A 108.5 . .
N1 C1 H1B 108.5 . .
C2 C1 H1B 108.5 . .
H1A C1 H1B 107.5 . .
C3 C2 C7 117.91(17) . .
C3 C2 C1 121.55(17) . .
C7 C2 C1 120.50(17) . .
C2 C3 C4 121.17(19) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C5 C4 C3 120.3(2) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C6 C5 C4 119.39(19) . .
C6 C5 H5 120.3 . .
C4 C5 H5 120.3 . .
C5 C6 C7 120.3(2) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C2 C7 C6 121.0(2) . .
C2 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
N1 C8 C9 114.94(15) . .
N1 C8 H8A 108.5 . .
C9 C8 H8A 108.5 . .
N1 C8 H8B 108.5 . .
C9 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
C10 C9 C14 117.95(18) . .
C10 C9 C8 119.38(18) . .
C14 C9 C8 122.60(16) . .
C9 C10 C11 120.7(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 120.4(2) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C13 C12 C11 119.6(2) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 120.2(2) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C9 C14 C13 121.1(2) . .
C9 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
N1 C15 C16 121.76(16) . .
N1 C15 C20 121.54(15) . .
C16 C15 C20 116.70(15) . .
C17 C16 C15 121.32(16) . .
C17 C16 H16 119.3 . .
C15 C16 H16 119.3 . .
C18 C17 C16 121.01(15) . .
C18 C17 C21 121.51(16) . .
C16 C17 C21 117.46(15) . .
C17 C18 C19 118.24(16) . .
C17 C18 H18 120.9 . .
C19 C18 H18 120.9 . .
C20 C19 C18 120.99(16) . .
C20 C19 C22 117.06(15) . .
C18 C19 C22 121.88(16) . .
C19 C20 C15 121.72(15) . .
C19 C20 H20 119.1 . .
C15 C20 H20 119.1 . .
O1 C21 O2 123.25(16) . .
O1 C21 C17 124.20(16) . .
O2 C21 C17 112.54(15) . .
O3 C22 O4 123.27(17) . .
O3 C22 C19 124.07(18) . .
O4 C22 C19 112.63(15) . .
O2 C23 H23A 109.5 . .
O2 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O2 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O4 C24 H24A 109.5 . .
O4 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O4 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C15 N1 C1 120.65(14) . .
C15 N1 C8 120.38(15) . .
C1 N1 C8 118.57(15) . .
C21 O2 C23 116.90(15) . .
C22 O4 C24 116.26(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.447(2) .
C1 C2 1.506(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.366(2) .
C2 C7 1.375(3) .
C3 C4 1.375(3) .
C3 H3 0.9300 .
C4 C5 1.364(3) .
C4 H4 0.9300 .
C5 C6 1.358(3) .
C5 H5 0.9300 .
C6 C7 1.377(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 N1 1.449(2) .
C8 C9 1.511(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.370(3) .
C9 C14 1.375(3) .
C10 C11 1.377(3) .
C10 H10 0.9300 .
C11 C12 1.363(3) .
C11 H11 0.9300 .
C12 C13 1.352(3) .
C12 H12 0.9300 .
C13 C14 1.376(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 N1 1.376(2) .
C15 C16 1.395(2) .
C15 C20 1.399(2) .
C16 C17 1.384(2) .
C16 H16 0.9300 .
C17 C18 1.382(2) .
C17 C21 1.484(2) .
C18 C19 1.383(2) .
C18 H18 0.9300 .
C19 C20 1.374(2) .
C19 C22 1.485(2) .
C20 H20 0.9300 .
C21 O1 1.201(2) .
C21 O2 1.325(2) .
C22 O3 1.193(2) .
C22 O4 1.327(2) .
C23 O2 1.439(2) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 O4 1.430(2) .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
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
N1 C1 C2 C3 -19.0(2) . . . .
N1 C1 C2 C7 163.57(16) . . . .
C7 C2 C3 C4 0.2(3) . . . .
C1 C2 C3 C4 -177.28(18) . . . .
C2 C3 C4 C5 -0.3(3) . . . .
C3 C4 C5 C6 0.4(3) . . . .
C4 C5 C6 C7 -0.3(3) . . . .
C3 C2 C7 C6 -0.2(3) . . . .
C1 C2 C7 C6 177.35(18) . . . .
C5 C6 C7 C2 0.2(3) . . . .
N1 C8 C9 C10 157.45(17) . . . .
N1 C8 C9 C14 -25.7(3) . . . .
C14 C9 C10 C11 -2.0(3) . . . .
C8 C9 C10 C11 174.95(18) . . . .
C9 C10 C11 C12 1.6(3) . . . .
C10 C11 C12 C13 0.2(4) . . . .
C11 C12 C13 C14 -1.6(4) . . . .
C10 C9 C14 C13 0.7(3) . . . .
C8 C9 C14 C13 -176.19(19) . . . .
C12 C13 C14 C9 1.1(3) . . . .
N1 C15 C16 C17 -178.18(14) . . . .
C20 C15 C16 C17 1.5(2) . . . .
C15 C16 C17 C18 -1.3(2) . . . .
C15 C16 C17 C21 177.11(14) . . . .
C16 C17 C18 C19 0.4(2) . . . .
C21 C17 C18 C19 -177.94(14) . . . .
C17 C18 C19 C20 0.2(2) . . . .
C17 C18 C19 C22 176.90(14) . . . .
C18 C19 C20 C15 0.2(2) . . . .
C22 C19 C20 C15 -176.69(14) . . . .
N1 C15 C20 C19 178.70(15) . . . .
C16 C15 C20 C19 -1.0(2) . . . .
C18 C17 C21 O1 177.42(16) . . . .
C16 C17 C21 O1 -0.9(2) . . . .
C18 C17 C21 O2 -1.1(2) . . . .
C16 C17 C21 O2 -179.43(14) . . . .
C20 C19 C22 O3 -3.5(3) . . . .
C18 C19 C22 O3 179.62(17) . . . .
C20 C19 C22 O4 174.38(14) . . . .
C18 C19 C22 O4 -2.5(2) . . . .
C16 C15 N1 C1 5.0(2) . . . .
C20 C15 N1 C1 -174.69(15) . . . .
C16 C15 N1 C8 177.67(15) . . . .
C20 C15 N1 C8 -2.0(2) . . . .
C2 C1 N1 C15 -77.5(2) . . . .
C2 C1 N1 C8 109.73(17) . . . .
C9 C8 N1 C15 -72.6(2) . . . .
C9 C8 N1 C1 100.20(19) . . . .
O1 C21 O2 C23 0.2(2) . . . .
C17 C21 O2 C23 178.69(14) . . . .
O3 C22 O4 C24 3.1(3) . . . .
C19 C22 O4 C24 -174.78(15) . . . .
