#------------------------------------------------------------------------------
#$Date: 2020-02-12 02:27:11 +0200 (Wed, 12 Feb 2020) $
#$Revision: 248053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037904.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_4037904
loop_
_publ_author_name
'Rahim, Abdur'
'Sahariah, Biswajit'
'Baruah, Kalpita'
'Deka, Jugal Kishore Rai'
'Sarma, Bani Kanta'
_publ_section_title
;
 Solid-phase Synthesis of Hybrid 2,5-Diketopiperazines Using
 Acylhydrazide, Carbazate, Semicarbazide, Amino Acid and Primary Amine
 Submonomers.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02083
_journal_year                    2020
_chemical_formula_moiety         'C20 H20 N4 O6'
_chemical_formula_sum            'C20 H20 N4 O6'
_chemical_formula_weight         412.40
_chemical_name_systematic
'dibenzyl (2,5-dioxopiperazine-1,4-diyl)dicarbamate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2019-12-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   20.0913(9)
_cell_length_b                   5.7683(3)
_cell_length_c                   8.6111(3)
_cell_measurement_reflns_used    6706
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      3.10
_cell_volume                     980.49(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15073
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.063
_diffrn_source                   X-ray
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless'
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.4952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1717
_reflns_number_total             1998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02083_si_002.cif
_cod_data_source_block           Comp32_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        980.48(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037904
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O 0.49510(6) 0.60953(18) 0.33147(13) 0.0422(3) Uani 1 1 d . .
O2 O 0.65287(6) 0.57314(19) 0.59584(13) 0.0410(3) Uani 1 1 d . .
N2 N 0.55766(6) 0.8958(2) 0.46493(14) 0.0311(3) Uani 1 1 d . .
O1 O 0.68797(7) 0.5702(3) 0.36192(16) 0.0596(4) Uani 1 1 d . .
N1 N 0.61280(7) 0.8299(2) 0.39831(17) 0.0390(3) Uani 1 1 d . .
C9 C 0.49870(7) 0.7831(2) 0.41301(15) 0.0301(3) Uani 1 1 d . .
C8 C 0.65087(7) 0.6494(3) 0.46502(17) 0.0337(3) Uani 1 1 d . .
C10 C 0.56301(8) 1.1273(3) 0.53114(18) 0.0352(4) Uani 1 1 d . .
H10A H 0.5738 1.2333 0.4519 0.042 Uiso 1 1 calc R U
H10B H 0.6008 1.1300 0.6197 0.042 Uiso 1 1 calc R U
C1 C 0.80249(9) 0.4416(3) 0.3709(2) 0.0498(4) Uani 1 1 d . .
C7 C 0.73500(11) 0.3860(4) 0.4129(3) 0.0635(6) Uani 1 1 d . .
H7A H 0.7178 0.2422 0.3623 0.076 Uiso 1 1 calc R U
H7B H 0.7401 0.3659 0.5263 0.076 Uiso 1 1 calc R U
C6 C 0.81411(12) 0.6327(4) 0.2846(3) 0.0677(6) Uani 1 1 d . .
H6 H 0.7789 0.7352 0.2483 0.081 Uiso 1 1 calc R U
C2 C 0.85552(11) 0.2913(5) 0.4215(3) 0.0739(7) Uani 1 1 d . .
H2 H 0.8485 0.1602 0.4792 0.089 Uiso 1 1 calc R U
C5 C 0.87807(13) 0.6741(5) 0.2511(4) 0.0883(8) Uani 1 1 d . .
H5 H 0.8856 0.8045 0.1933 0.106 Uiso 1 1 calc R U
C4 C 0.92974(13) 0.5239(6) 0.3028(4) 0.0974(10) Uani 1 1 d . .
H4 H 0.9725 0.5515 0.2802 0.117 Uiso 1 1 calc R U
C3 C 0.91859(13) 0.3335(6) 0.3875(4) 0.0989(10) Uani 1 1 d . .
H3 H 0.9539 0.2311 0.4227 0.119 Uiso 1 1 calc R U
H1N H 0.6093(11) 0.860(4) 0.298(3) 0.061(6) Uiso 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
C9 N2 N1 116.61(12) . .
C9 N2 C10 124.72(12) . .
N1 N2 C10 114.06(12) . .
C8 O1 C7 117.73(14) . .
C8 N1 N2 117.71(12) . .
C8 N1 H1N 120.6(14) . .
N2 N1 H1N 115.5(14) . .
O3 C9 N2 122.70(14) . .
O3 C9 C10 120.24(13) . 3_676
N2 C9 C10 116.96(12) . 3_676
O2 C8 O1 124.70(14) . .
O2 C8 N1 126.58(14) . .
O1 C8 N1 108.70(13) . .
N2 C10 C9 115.97(12) . 3_676
N2 C10 H10A 108.3 . .
C9 C10 H10A 108.3 3_676 .
N2 C10 H10B 108.3 . .
C9 C10 H10B 108.3 3_676 .
H10A C10 H10B 107.4 . .
C6 C1 C2 118.4(2) . .
C6 C1 C7 123.65(17) . .
C2 C1 C7 117.92(19) . .
O1 C7 C1 109.91(16) . .
O1 C7 H7A 109.7 . .
C1 C7 H7A 109.7 . .
O1 C7 H7B 109.7 . .
C1 C7 H7B 109.7 . .
H7A C7 H7B 108.2 . .
C1 C6 C5 120.5(2) . .
C1 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C3 C2 C1 120.6(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C4 C5 C6 120.1(3) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C3 C4 C5 119.8(2) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C3 C2 120.5(3) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C9 1.2174(17) .
O2 C8 1.2031(18) .
N2 C9 1.3521(19) .
N2 N1 1.3921(17) .
N2 C10 1.4482(18) .
O1 C8 1.3414(18) .
O1 C7 1.435(2) .
N1 C8 1.354(2) .
N1 H1N 0.87(2) .
C9 C10 1.503(2) 3_676
C10 C9 1.503(2) 3_676
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C1 C6 1.374(3) .
C1 C2 1.380(3) .
C1 C7 1.502(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C6 C5 1.389(3) .
C6 H6 0.9300 .
C2 C3 1.375(3) .
C2 H2 0.9300 .
C5 C4 1.361(4) .
C5 H5 0.9300 .
C4 C3 1.360(4) .
C4 H4 0.9300 .
C3 H3 0.9300 .
