#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/13/2211304.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_2211304
loop_
_publ_author_name
'Wei Wang'
'Yong Huang'
'Ning Tang'
_publ_section_title
N,N'-1,2-Ethanediylbis{2-[(N-benzylcarbamoyl)methoxy]benzamide}
_journal_coeditor_code           BM2009
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5557
_journal_page_last               o5559
_journal_paper_doi               10.1107/S1600536806046496
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C34 H34 N4 O6'
_chemical_formula_moiety         'C34 H34 N4 O6'
_chemical_formula_sum            'C34 H34 N4 O6'
_chemical_formula_weight         594.65
_chemical_melting_point          485.0(10)
_chemical_name_systematic
;
N,N'-1,2-Ethanediylbis{2-[(N-benzylcarbamoyl)methoxy]benzamide}
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.4570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7401(3)
_cell_length_b                   13.6100(4)
_cell_length_c                   8.8838(2)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.23
_cell_volume                     1484.67(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2005)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'π and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8214
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       0.0079(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0413
_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)+(0.055P)²+0.258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.118
_reflns_number_gt                2210
_reflns_number_total             2913
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm2009.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '484--486' was changed to '485.0(10)'
- the average value was taken and precision was estimated.

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

The following automatic conversions were performed:

'_chemical_melting_point' value '484--486' was changed to '485.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211304
_cod_database_fobs_code          2211304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.17595(11) 0.25771(11) 0.91492(16) 0.0504(4) Uani d . 1
H H1' 0.1870 0.2874 0.8350 0.060 Uiso calc R 1
N N2 0.49183(10) 0.03475(10) 1.29381(14) 0.0426(3) Uani d . 1
H H2' 0.4476 0.0788 1.2439 0.051 Uiso calc R 1
O O1 0.25705(9) 0.17763(9) 1.13967(12) 0.0518(3) Uani d . 1
O O2 0.44671(8) 0.17085(9) 1.07389(12) 0.0481(3) Uani d . 1
O O3 0.64868(10) -0.04712(9) 1.32030(14) 0.0573(4) Uani d . 1
C C1 -0.00411(13) 0.17964(13) 0.8242(2) 0.0516(4) Uani d . 1
C C2 0.02140(18) 0.08153(17) 0.8445(3) 0.0854(7) Uani d . 1
H H2 0.0806 0.0622 0.9253 0.103 Uiso calc R 1
C C3 -0.0388(2) 0.0116(2) 0.7479(4) 0.1148(11) Uani d . 1
H H3 -0.0208 -0.0545 0.7649 0.138 Uiso calc R 1
C C4 -0.1257(2) 0.0384(2) 0.6259(3) 0.0975(8) Uani d . 1
H H4 -0.1644 -0.0088 0.5575 0.117 Uiso calc R 1
C C5 -0.15405(16) 0.1345(2) 0.6067(3) 0.0795(7) Uani d . 1
H H5 -0.2140 0.1532 0.5265 0.095 Uiso calc R 1
C C6 -0.09416(14) 0.20525(16) 0.7060(2) 0.0653(6) Uani d . 1
H H6 -0.1151 0.2708 0.6926 0.078 Uiso calc R 1
C C7 0.06510(13) 0.25416(14) 0.9312(2) 0.0558(5) Uani d . 1
H H7A 0.0320 0.3185 0.9084 0.067 Uiso calc R 1
H H7B 0.0674 0.2381 1.0384 0.067 Uiso calc R 1
C C8 0.26126(12) 0.21738(11) 1.01725(17) 0.0399(4) Uani d . 1
C C9 0.36552(12) 0.22538(12) 0.96690(18) 0.0435(4) Uani d . 1
H H9A 0.3546 0.1993 0.8622 0.052 Uiso calc R 1
H H9B 0.3874 0.2936 0.9668 0.052 Uiso calc R 1
C C10 0.54140(11) 0.14867(11) 1.03464(17) 0.0383(4) Uani d . 1
C C11 0.57218(13) 0.19701(12) 0.91583(18) 0.0464(4) Uani d . 1
H H11 0.5281 0.2462 0.8594 0.056 Uiso calc R 1
C C12 0.66791(14) 0.17220(13) 0.8813(2) 0.0532(4) Uani d . 1
H H12 0.6879 0.2046 0.8010 0.064 Uiso calc R 1
C C13 0.73428(14) 0.09991(14) 0.9643(2) 0.0572(5) Uani d . 1
H H13 0.7987 0.0831 0.9403 0.069 Uiso calc R 1
C C14 0.70393(13) 0.05271(13) 1.0837(2) 0.0488(4) Uani d . 1
H H14 0.7494 0.0045 1.1405 0.059 Uiso calc R 1
C C15 0.60748(12) 0.07487(11) 1.12169(16) 0.0377(4) Uani d . 1
C C16 0.58391(12) 0.01605(11) 1.25268(17) 0.0404(4) Uani d . 1
C C17 0.46568(13) -0.01805(12) 1.42096(17) 0.0451(4) Uani d . 1
H H17A 0.4785 -0.0877 1.4107 0.054 Uiso calc R 1
H H17B 0.3891 -0.0091 1.4150 0.054 Uiso calc R 1
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
C2 C1 C6 . . 117.75(19)
C2 C1 C7 . . 119.57(16)
C6 C1 C7 . . 122.68(17)
C3 C2 C1 . . 121.3(2)
C3 C2 H2 . . 119.4
C1 C2 H2 . . 119.4
C2 C3 C4 . . 120.5(3)
C2 C3 H3 . . 119.8
C4 C3 H3 . . 119.8
C5 C4 C3 . . 119.1(2)
C5 C4 H4 . . 120.4
C3 C4 H4 . . 120.4
C4 C5 C6 . . 120.4(2)
C4 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C1 C6 C5 . . 120.9(2)
C1 C6 H6 . . 119.5
C5 C6 H6 . . 119.5
N1 C7 C1 . . 112.29(14)
N1 C7 H7A . . 109.1
C1 C7 H7A . . 109.1
N1 C7 H7B . . 109.1
C1 C7 H7B . . 109.1
H7A C7 H7B . . 107.9
O1 C8 N1 . . 124.34(15)
O1 C8 C9 . . 122.81(14)
N1 C8 C9 . . 112.85(13)
O2 C9 C8 . . 107.81(12)
O2 C9 H9A . . 110.1
C8 C9 H9A . . 110.1
O2 C9 H9B . . 110.1
C8 C9 H9B . . 110.1
H9A C9 H9B . . 108.5
O2 C10 C11 . . 122.28(14)
O2 C10 C15 . . 117.08(13)
C11 C10 C15 . . 120.63(14)
C12 C11 C10 . . 120.04(16)
C12 C11 H11 . . 120.0
C10 C11 H11 . . 120.0
C11 C12 C13 . . 120.67(16)
C11 C12 H12 . . 119.7
C13 C12 H12 . . 119.7
C12 C13 C14 . . 119.10(16)
C12 C13 H13 . . 120.4
C14 C13 H13 . . 120.4
C13 C14 C15 . . 122.14(16)
C13 C14 H14 . . 118.9
C15 C14 H14 . . 118.9
C14 C15 C10 . . 117.40(14)
C14 C15 C16 . . 116.29(14)
C10 C15 C16 . . 126.31(13)
O3 C16 N2 . . 121.34(14)
O3 C16 C15 . . 120.13(14)
N2 C16 C15 . . 118.53(13)
N2 C17 C17 . 3_658 111.30(16)
N2 C17 H17A . . 109.4
C17 C17 H17A 3_658 . 109.4
N2 C17 H17B . . 109.4
C17 C17 H17B 3_658 . 109.4
H17A C17 H17B . . 108.0
C8 N1 C7 . . 123.57(14)
C8 N1 H1' . . 118.2
C7 N1 H1' . . 118.2
C16 N2 C17 . . 121.10(13)
C16 N2 H2' . . 119.4
C17 N2 H2' . . 119.4
C10 O2 C9 . . 118.59(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.375(3)
C1 C6 . 1.377(2)
C1 C7 . 1.505(2)
C2 C3 . 1.371(3)
C2 H2 . 0.9300
C3 C4 . 1.376(4)
C3 H3 . 0.9300
C4 C5 . 1.356(4)
C4 H4 . 0.9300
C5 C6 . 1.389(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 N1 . 1.458(2)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 O1 . 1.2286(18)
C8 N1 . 1.3351(19)
C8 C9 . 1.514(2)
C9 O2 . 1.4142(17)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 O2 . 1.3757(18)
C10 C11 . 1.386(2)
C10 C15 . 1.403(2)
C11 C12 . 1.377(2)
C11 H11 . 0.9300
C12 C13 . 1.376(2)
C12 H12 . 0.9300
C13 C14 . 1.380(2)
C13 H13 . 0.9300
C14 C15 . 1.391(2)
C14 H14 . 0.9300
C15 C16 . 1.507(2)
C16 O3 . 1.2315(18)
C16 N2 . 1.343(2)
C17 N2 . 1.4506(19)
C17 C17 3_658 1.524(3)
C17 H17A . 0.9700
C17 H17B . 0.9700
N1 H1' . 0.8600
N2 H2' . 0.8600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2' O2 . 0.86 1.96 2.642(3) 135 yes
N1 H1' O1 4_565 0.86 2.20 3.028(3) 160 yes
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . 1.8(4)
C7 C1 C2 C3 . -179.0(2)
C1 C2 C3 C4 . 1.1(5)
C2 C3 C4 C5 . -3.0(5)
C3 C4 C5 C6 . 1.9(4)
C2 C1 C6 C5 . -2.8(3)
C7 C1 C6 C5 . 178.06(17)
C4 C5 C6 C1 . 1.0(3)
C2 C1 C7 N1 . 64.8(2)
C6 C1 C7 N1 . -116.13(18)
O1 C8 C9 O2 . 6.5(2)
N1 C8 C9 O2 . -173.38(13)
O2 C10 C11 C12 . 179.87(14)
C15 C10 C11 C12 . 0.6(2)
C10 C11 C12 C13 . -0.4(3)
C11 C12 C13 C14 . -0.3(3)
C12 C13 C14 C15 . 0.9(3)
C13 C14 C15 C10 . -0.7(2)
C13 C14 C15 C16 . 178.86(15)
O2 C10 C15 C14 . -179.38(13)
C11 C10 C15 C14 . -0.1(2)
O2 C10 C15 C16 . 1.1(2)
C11 C10 C15 C16 . -179.54(14)
C14 C15 C16 O3 . 0.4(2)
C10 C15 C16 O3 . 179.93(14)
C14 C15 C16 N2 . 179.96(13)
C10 C15 C16 N2 . -0.6(2)
O1 C8 N1 C7 . -4.0(2)
C9 C8 N1 C7 . 175.95(15)
C1 C7 N1 C8 . -103.28(19)
O3 C16 N2 C17 . 0.7(2)
C15 C16 N2 C17 . -178.78(12)
C17 C17 N2 C16 3_658 75.2(2)
C11 C10 O2 C9 . 16.5(2)
C15 C10 O2 C9 . -164.18(13)
C8 C9 O2 C10 . 165.77(12)
