#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/86/2008639.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_2008639
loop_
_publ_author_name
'Bolte, Michael'
'Benecke, Bernd'
'Egert, Ernst'
_publ_section_title
;
 Bis-lactim ethers of cyclic dipeptides. 2. Benzyl-substituted
 compounds
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              968
_journal_page_last               973
_journal_paper_doi               10.1107/S010827019801645X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.40
_chemical_name_systematic
;
(3S,6S)-3,6-Dibenzyl-2,5-dimethoxy-3,6-dihydro-pyrazine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9980(10)
_cell_length_b                   11.5130(10)
_cell_length_c                   14.4640(10)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    293
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1831.4(3)
_computing_cell_refinement       D4
_computing_data_collection       'D4 (Clegg, 1981)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1988)'
_computing_molecular_graphics    'XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Stoe Siemens four-circle diffractometer'
_diffrn_measurement_method       'ω-θ scans with learnt profile (Clegg, 1981)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1840
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.54
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.107
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_all   1.080
_refine_ls_goodness_of_fit_obs   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_restrained_S_obs      1.121
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_obs          .0418
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0432P)²+0.3472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1032
_refine_ls_wR_factor_obs         .0971
_reflns_number_observed          1548
_reflns_number_total             1840
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            sk1255.cif
_cod_data_source_block           II
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.3472P] 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^)+(0.0432P)^2^+0.3472P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008639
_cod_database_fobs_code          2008639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .9627(2) .3892(2) .57447(15) .0528(6) Uani d . 1 . N
C2 .8726(2) .3913(3) .52153(18) .0468(7) Uani d . 1 . C
C3 .7403(2) .3834(2) .54567(18) .0444(6) Uani d . 1 . C
H3 .7053 .3214 .5077 .053 Uiso calc R 1 . H
N4 .7196(2) .3525(2) .64166(15) .0495(6) Uani d . 1 . N
C5 .8082(3) .3557(3) .69543(19) .0504(7) Uani d . 1 . C
C6 .9389(3) .3816(3) .67374(18) .0554(8) Uani d . 1 . C
H6 .9874 .3168 .6977 .067 Uiso calc R 1 . H
O21 .88685(17) .3997(2) .42840(12) .0606(6) Uani d . 1 . O
C22 1.0092(3) .3990(4) .3952(2) .0847(12) Uani d . 1 . C
H22A 1.0091 .4053 .3290 .102 Uiso calc R 1 . H
H22B 1.0480 .3277 .4130 .102 Uiso calc R 1 . H
H22C 1.0527 .4634 .4212 .102 Uiso calc R 1 . H
O51 .7955(2) .3334(2) .78753(14) .0704(7) Uani d . 1 . O
C52 .6730(4) .3159(4) .8194(3) .0888(13) Uani d . 1 . C
H52A .6736 .3010 .8847 .107 Uiso calc R 1 . H
H52B .6378 .2507 .7878 .107 Uiso calc R 1 . H
H52C .6257 .3842 .8071 .107 Uiso calc R 1 . H
C1' .6704(2) .4953(2) .5229(2) .0471(7) Uani d . 1 . C
H1'A .6989 .5576 .5625 .056 Uiso calc R 1 . H
H1'B .6864 .5173 .4593 .056 Uiso calc R 1 . H
C2' .5355(2) .4796(2) .53621(18) .0428(6) Uani d . 1 . C
C3' .4772(3) .5204(3) .6140(2) .0610(8) Uani d . 1 . C
H3' .5211 .5602 .6589 .091 Uiso calc R 1 . H
C4' .3534(3) .5023(3) .6260(3) .0755(10) Uani d . 1 . C
H4' .3153 .5296 .6792 .113 Uiso calc R 1 . H
C5' .2870(3) .4449(3) .5607(3) .0679(9) Uani d . 1 . C
H5' .2042 .4325 .5694 .102 Uiso calc R 1 . H
C6' .3436(3) .4056(3) .4820(2) .0562(8) Uani d . 1 . C
H6' .2988 .3683 .4363 .084 Uiso calc R 1 . H
C7' .4667(2) .4217(2) .4710(2) .0486(7) Uani d . 1 . C
H7' .5046 .3928 .4184 .073 Uiso calc R 1 . H
C1" .9838(3) .4924(3) .7222(2) .0645(9) Uani d . 1 . C
H1"A .9782 .4811 .7885 .077 Uiso calc R 1 . H
H1"B 1.0689 .5037 .7071 .077 Uiso calc R 1 . H
C2" .9153(3) .6002(3) .69698(19) .0560(8) Uani d . 1 . C
C3" .9494(4) .6680(3) .6227(2) .0785(11) Uani d . 1 . C
H3" 1.0174 .6475 .5881 .118 Uiso calc R 1 . H
C4" .8831(5) .7666(4) .5990(3) .0993(15) Uani d . 1 . C
H4" .9067 .8113 .5485 .149 Uiso calc R 1 . H
C5" .7830(5) .7979(4) .6500(3) .1005(14) Uani d . 1 . C
H5" .7384 .8636 .6340 .151 Uiso calc R 1 . H
C6" .7491(3) .7321(3) .7240(3) .0806(11) Uani d . 1 . C
H6" .6821 .7537 .7592 .121 Uiso calc R 1 . H
C7" .8139(3) .6341(3) .7469(2) .0598(8) Uani d . 1 . C
H7" .7891 .5895 .7971 .090 Uiso calc R 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
_geom_angle_publ_flag
C2 N1 C6 117.4(2) yes
N1 C2 O21 121.1(2) yes
N1 C2 C3 128.6(3) yes
O21 C2 C3 110.3(2) yes
N4 C3 C2 113.0(2) yes
N4 C3 C1' 109.4(2) yes
C2 C3 C1' 112.7(2) ?
C5 N4 C3 117.8(2) yes
N4 C5 O51 121.6(3) yes
N4 C5 C6 128.6(3) yes
O51 C5 C6 109.8(3) yes
N1 C6 C5 112.8(2) yes
N1 C6 C1" 109.9(3) yes
C5 C6 C1" 112.2(3) ?
C2 O21 C22 116.2(2) ?
C5 O51 C52 115.8(3) ?
C2' C1' C3 111.4(2) ?
C3' C2' C7' 117.9(3) ?
C3' C2' C1' 121.5(3) ?
C7' C2' C1' 120.7(3) ?
C2' C3' C4' 120.5(3) ?
C5' C4' C3' 120.7(3) ?
C4' C5' C6' 119.4(3) ?
C5' C6' C7' 119.8(3) ?
C6' C7' C2' 121.7(3) ?
C2" C1" C6 114.5(2) ?
C3" C2" C7" 117.8(3) ?
C3" C2" C1" 121.4(3) ?
C7" C2" C1" 120.8(3) ?
C2" C3" C4" 120.7(4) ?
C5" C4" C3" 120.1(4) ?
C6" C5" C4" 119.7(4) ?
C5" C6" C7" 120.2(4) ?
C6" C7" C2" 121.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.253(3) yes
N1 C6 . 1.462(4) yes
C2 O21 . 1.360(3) yes
C2 C3 . 1.499(4) ?
C3 N4 . 1.451(3) yes
C3 C1' . 1.536(4) ?
N4 C5 . 1.248(4) yes
C5 O51 . 1.364(3) yes
C5 C6 . 1.501(4) ?
C6 C1" . 1.537(4) ?
O21 C22 . 1.429(4) yes
O51 C52 . 1.439(4) yes
C1' C2' . 1.508(4) ?
C2' C3' . 1.378(4) ?
C2' C7' . 1.380(4) ?
C3' C4' . 1.388(4) ?
C4' C5' . 1.365(5) ?
C5' C6' . 1.374(4) ?
C6' C7' . 1.376(4) ?
C1" C2" . 1.497(5) ?
C2" C3" . 1.380(4) ?
C2" C7" . 1.385(4) ?
C3" C4" . 1.392(6) ?
C4" C5" . 1.374(6) ?
C5" C6" . 1.363(6) ?
C6" C7" . 1.375(5) ?
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
C6 N1 C2 O21 179.1(3)
C6 N1 C2 C3 -2.0(5)
N1 C2 C3 N4 -9.8(4)
O21 C2 C3 N4 169.1(2)
N1 C2 C3 C1' 114.9(3)
O21 C2 C3 C1' -66.2(3)
C2 C3 N4 C5 11.9(4)
C1' C3 N4 C5 -114.5(3)
C3 N4 C5 O51 176.8(2)
C3 N4 C5 C6 -3.7(5)
C2 N1 C6 C5 10.5(4)
C2 N1 C6 C1" -115.5(3)
N4 C5 C6 N1 -8.2(5)
O51 C5 C6 N1 171.4(2)
N4 C5 C6 C1" 116.6(4)
O51 C5 C6 C1" -63.8(3)
N1 C2 O21 C22 3.6(5)
C3 C2 O21 C22 -175.4(3)
N4 C5 O51 C52 -5.0(5)
C6 C5 O51 C52 175.3(3)
N4 C3 C1' C2' -60.8(3)
C2 C3 C1' C2' 172.6(2)
C3 C1' C2' C3' 101.1(3)
C3 C1' C2' C7' -77.7(3)
C7' C2' C3' C4' 0.5(5)
C1' C2' C3' C4' -178.3(3)
C2' C3' C4' C5' -0.6(6)
C3' C4' C5' C6' -0.6(6)
C4' C5' C6' C7' 1.8(5)
C5' C6' C7' C2' -1.9(5)
C3' C2' C7' C6' 0.7(4)
C1' C2' C7' C6' 179.6(3)
N1 C6 C1" C2" 66.6(3)
C5 C6 C1" C2" -59.8(3)
C6 C1" C2" C3" -88.9(4)
C6 C1" C2" C7" 90.0(3)
C7" C2" C3" C4" -0.4(5)
C1" C2" C3" C4" 178.6(3)
C2" C3" C4" C5" 0.4(6)
C3" C4" C5" C6" 0.2(6)
C4" C5" C6" C7" -0.9(6)
C5" C6" C7" C2" 0.9(5)
C3" C2" C7" C6" -0.3(4)
C1" C2" C7" C6" -179.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182997
2 PubChem 100984928
