#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/65/2206590.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206590
loop_
_publ_author_name
'Tang, Yu'
'Tang, Kuan-Zhen'
'Zhang, Jian'
_publ_section_title
;
 2,4-Bis[2-(benzylaminocarbonyl)phenoxymethyl]-1,3,5-trimethylbenzene
;
_journal_coeditor_code           WW6370
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2489
_journal_page_last               o2490
_journal_paper_doi               10.1107/S1600536805021537
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C39 H38 N2 O4'
_chemical_formula_moiety         'C39 H38 N2 O4'
_chemical_formula_sum            'C39 H38 N2 O4'
_chemical_formula_weight         598.71
_chemical_name_systematic
;
2,4-Bis[2-(benzylaminocarbonyl)phenoxymethyl]-1,3,5-trimethylbenzene
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 126.097(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5494(10)
_cell_length_b                   12.1369(10)
_cell_length_c                   16.3862(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.5
_cell_volume                     3302.2(6)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3668
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 800
_diffrn_standards_interval_time  3600
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.174
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.055P)²+1.5772P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                1596
_reflns_number_total             3247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6370.cif
_cod_data_source_block           I
_cod_original_cell_volume        3302.2(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2206590
_cod_database_fobs_code          2206590
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.24428(12) 0.9937(2) 0.75463(12) 0.1060(8) Uani d . 1 O
O2 0.17522(9) 0.98704(16) 0.46259(10) 0.0791(6) Uani d . 1 O
N1 0.15951(15) 0.9207(2) 0.60286(17) 0.0967(9) Uani d . 1 N
C1 0.0675(3) 0.6983(5) 0.5300(3) 0.1213(14) Uani d . 1 C
C2 0.0069(5) 0.6294(5) 0.4544(5) 0.1325(16) Uani d . 1 C
C3 -0.0703(4) 0.6627(6) 0.4021(4) 0.1303(17) Uani d . 1 C
C4 -0.0890(3) 0.7611(6) 0.4207(3) 0.1257(14) Uani d . 1 C
C5 -0.0303(3) 0.8265(4) 0.4942(3) 0.1112(12) Uani d . 1 C
C6 0.0478(3) 0.7973(4) 0.5497(2) 0.0987(11) Uani d . 1 C
C7 0.1119(2) 0.8702(4) 0.6318(2) 0.1478(17) Uani d U 1 C
H7A 0.0871 0.9273 0.6464 0.177 Uiso calc R 1 H
H7B 0.1468 0.8271 0.6928 0.177 Uiso calc R 1 H
C8 0.22227(15) 0.9830(2) 0.66751(17) 0.0723(7) Uani d . 1 C
C9 0.26741(14) 1.0357(2) 0.63300(16) 0.0607(6) Uani d . 1 C
C10 0.33870(18) 1.0874(2) 0.7070(2) 0.0813(8) Uani d . 1 C
C11 0.3877(2) 1.1351(3) 0.6872(3) 0.1090(12) Uani d . 1 C
C12 0.3659(2) 1.1339(3) 0.5908(3) 0.1128(12) Uani d . 1 C
C13 0.29611(18) 1.0845(3) 0.5147(2) 0.0907(10) Uani d . 1 C
C14 0.24615(14) 1.0359(2) 0.53503(16) 0.0642(7) Uani d . 1 C
C15 0.1510(2) 0.9776(4) 0.36065(19) 0.0868(10) Uani d . 1 C
C16 0.07260(15) 0.9175(3) 0.30263(15) 0.0647(7) Uani d . 1 C
C17 0.07246(17) 0.8034(3) 0.30329(17) 0.0797(8) Uani d . 1 C
C18 0.0000 0.7499(5) 0.2500 0.0899(13) Uani d S 1 C
C19 0.1494(2) 0.7363(3) 0.3608(2) 0.1340(15) Uani d . 1 C
H19A 0.1364 0.6593 0.3508 0.201 Uiso calc R 1 H
H19B 0.1799 0.7534 0.4315 0.201 Uiso calc R 1 H
H19C 0.1808 0.7538 0.3365 0.201 Uiso calc R 1 H
C20 0.0000 1.1002(3) 0.2500 0.0968(14) Uani d S 1 C
H20A -0.0545 1.1266 0.2105 0.145 Uiso calc PR 0.50 H
H20B 0.0266 1.1266 0.2215 0.145 Uiso calc PR 0.50 H
H20C 0.0279 1.1266 0.3181 0.145 Uiso calc PR 0.50 H
C21 0.0000 0.9755(3) 0.2500 0.0611(9) Uani d S 1 C
H13 0.2812(12) 1.0846(18) 0.4500(17) 0.062(6) Uiso d . 1 H
H10 0.3513(14) 1.086(2) 0.7727(19) 0.085(8) Uiso d . 1 H
H1N 0.1431(16) 0.915(2) 0.539(2) 0.097(9) Uiso d . 1 H
H12 0.4033(18) 1.160(3) 0.574(2) 0.120(10) Uiso d . 1 H
H5 -0.041(2) 0.901(4) 0.514(3) 0.164(17) Uiso d . 1 H
H11 0.440(2) 1.169(3) 0.743(2) 0.139(12) Uiso d . 1 H
H18 0.0000 0.675(4) 0.2500 0.113(17) Uiso d S 1 H
H1 0.124(2) 0.685(3) 0.572(3) 0.137(15) Uiso d . 1 H
H2 0.027(2) 0.566(4) 0.445(3) 0.16(2) Uiso d . 1 H
H4 -0.148(3) 0.786(4) 0.382(3) 0.19(2) Uiso d . 1 H
H15B 0.1925(18) 0.940(3) 0.364(2) 0.111(12) Uiso d . 1 H
H15A 0.1472(18) 1.054(3) 0.336(2) 0.118(12) Uiso d . 1 H
H3 -0.115(3) 0.620(4) 0.348(4) 0.19(2) Uiso d . 1 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C14 O2 C15 . . 120.55(19)
C8 N1 C7 . . 120.5(2)
C8 N1 H1N . . 120.1(18)
C7 N1 H1N . . 119.2(18)
C6 C1 C2 . . 120.0(5)
C6 C1 H1 . . 112(2)
C2 C1 H1 . . 128(2)
C3 C2 C1 . . 118.9(5)
C3 C2 H2 . . 128(3)
C1 C2 H2 . . 113(3)
C4 C3 C2 . . 120.6(5)
C4 C3 H3 . . 116(3)
C2 C3 H3 . . 123(3)
C3 C4 C5 . . 120.0(5)
C3 C4 H4 . . 121(3)
C5 C4 H4 . . 119(3)
C6 C5 C4 . . 122.1(5)
C6 C5 H5 . . 114(2)
C4 C5 H5 . . 124(2)
C5 C6 C1 . . 118.3(4)
C5 C6 C7 . . 121.3(5)
C1 C6 C7 . . 120.4(5)
N1 C7 C6 . . 111.2(2)
N1 C7 H7A . . 109.4
C6 C7 H7A . . 109.4
N1 C7 H7B . . 109.4
C6 C7 H7B . . 109.4
H7A C7 H7B . . 108.0
O1 C8 N1 . . 120.7(2)
O1 C8 C9 . . 120.9(2)
N1 C8 C9 . . 118.3(2)
C10 C9 C14 . . 117.4(2)
C10 C9 C8 . . 115.9(2)
C14 C9 C8 . . 126.7(2)
C11 C10 C9 . . 122.3(3)
C11 C10 H10 . . 122.5(15)
C9 C10 H10 . . 115.2(15)
C10 C11 C12 . . 119.3(3)
C10 C11 H11 . . 120.1(19)
C12 C11 H11 . . 121(2)
C11 C12 C13 . . 120.9(3)
C11 C12 H12 . . 121.9(17)
C13 C12 H12 . . 116.8(17)
C12 C13 C14 . . 119.8(3)
C12 C13 H13 . . 120.8(14)
C14 C13 H13 . . 119.4(14)
O2 C14 C13 . . 122.8(2)
O2 C14 C9 . . 116.9(2)
C13 C14 C9 . . 120.3(2)
O2 C15 C16 . . 106.5(2)
O2 C15 H15B . . 106.9(18)
C16 C15 H15B . . 113.7(19)
O2 C15 H15A . . 107.0(19)
C16 C15 H15A . . 113.5(18)
H15B C15 H15A . . 109(3)
C17 C16 C21 . . 120.2(3)
C17 C16 C15 . . 119.4(3)
C21 C16 C15 . . 120.4(3)
C18 C17 C16 . . 118.5(3)
C18 C17 C19 . . 119.1(3)
C16 C17 C19 . . 122.4(3)
C17 C18 C17 . 2 123.2(5)
C17 C18 H18 . . 118.4(2)
C17 C18 H18 2 . 118.4(2)
C17 C19 H19A . . 109.5
C17 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
C17 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
C21 C20 H20A . . 109.5
C21 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C21 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
C16 C21 C16 2 . 119.4(3)
C16 C21 C20 2 . 120.30(17)
C16 C21 C20 . . 120.30(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C8 . 1.224(3)
O2 C14 . 1.359(3)
O2 C15 . 1.439(3)
N1 C8 . 1.322(3)
N1 C7 . 1.451(3)
N1 H1N . 0.90(3)
C1 C6 . 1.367(6)
C1 C2 . 1.402(7)
C1 H1 . 0.95(4)
C2 C3 . 1.347(7)
C2 H2 . 0.93(4)
C3 C4 . 1.343(6)
C3 H3 . 0.97(5)
C4 C5 . 1.350(6)
C4 H4 . 1.03(5)
C5 C6 . 1.345(5)
C5 H5 . 1.03(4)
C6 C7 . 1.497(4)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.486(3)
C9 C10 . 1.385(3)
C9 C14 . 1.393(3)
C10 C11 . 1.356(4)
C10 H10 . 0.95(2)
C11 C12 . 1.365(4)
C11 H11 . 1.01(3)
C12 C13 . 1.365(4)
C12 H12 . 1.01(3)
C13 C14 . 1.384(3)
C13 H13 . 0.91(2)
C15 C16 . 1.492(4)
C15 H15B . 0.94(3)
C15 H15A . 1.00(3)
C16 C17 . 1.384(4)
C16 C21 . 1.396(3)
C17 C18 . 1.368(4)
C17 C19 . 1.516(4)
C18 C17 2 1.368(4)
C18 H18 . 0.91(5)
C19 H19A . 0.9600
C19 H19B . 0.9600
C19 H19C . 0.9600
C20 C21 . 1.513(5)
C20 H20A . 0.9600
C20 H20B . 0.9600
C20 H20C . 0.9600
C21 C16 2 1.396(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O2 0.90(3) 1.93(3) 2.628(3) 133(3) yes
