#------------------------------------------------------------------------------
#$Date: 2022-02-15 23:54:02 +0100 (mar 15 de feb de 2022) $
#$Revision: 272975 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/97/7129717.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_7129717
loop_
_publ_author_name
'Li, Yutang'
'Strand, Daniel'
'Grimme, Stefan'
'Jónsson, Stefán'
'Wärnmark, Kenneth'
_publ_section_title
;
 The long-awaited synthesis and self-assembly of a small rigid C3
 symmetric trilactam
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00345G
_journal_year                    2022
_chemical_formula_moiety         'C7 H4 D3 N3 O3'
_chemical_formula_sum            'C7 H4 D3 N3 O3'
_chemical_formula_weight         184.17
_chemical_name_systematic
(2aS*,4aS*,6aS*)-hexahydro-1,3,5-triazacyclopenta[cd]pentalene-2,4,6(1H)-trione
_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-2016/6
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.738(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2905(7)
_cell_length_b                   11.3194(9)
_cell_length_c                   9.0781(10)
_cell_measurement_reflns_used    1190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9730
_cell_measurement_theta_min      4.3020
_cell_volume                     695.89(13)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0433
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4010
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.436
_diffrn_reflns_theta_min         3.506
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0518
_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)+(0.0451P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1206
_reflns_number_total             1622
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00345g2.cif
_cod_data_source_block           shelx_CCDC2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7129717
_shelx_shelxl_version_number     2016/6
_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.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4817(3) 0.68721(16) 1.0133(2) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.3157(3) 0.63812(15) 0.8689(2) 0.0268(4) Uani 1 1 d . . . . .
H4 H 0.365709 0.582239 0.810173 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0115(3) 0.64547(16) 0.8593(2) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.0116(3) 0.75474(14) 0.7693(2) 0.0256(4) Uani 1 1 d . . . . .
H3 H -0.088726 0.757568 0.661762 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1846(3) 0.92227(16) 0.9054(2) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.3340(3) 0.85433(15) 0.8588(2) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.389156 0.902083 0.795081 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2203(3) 0.74627(14) 0.7677(2) 0.0264(4) Uani 1 1 d . . . . .
H1 H 0.220572 0.741255 0.659989 0.032 Uiso 1 1 calc R U . . .
N1 N 0.4857(2) 0.80510(14) 0.9980(2) 0.0339(4) Uani 1 1 d . . . . .
N2 N 0.1591(2) 0.58646(14) 0.91016(19) 0.0282(4) Uani 1 1 d . . . . .
N3 N 0.0139(2) 0.86299(13) 0.85715(19) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.5887(2) 0.62884(12) 1.12505(17) 0.0387(4) Uani 1 1 d . . . . .
O2 O -0.1621(2) 0.61782(12) 0.88163(18) 0.0419(4) Uani 1 1 d . . . . .
O3 O 0.2190(2) 1.01594(12) 0.97953(17) 0.0389(4) Uani 1 1 d . . . . .
D1 D -0.088(3) 0.889(2) 0.870(3) 0.047 Uiso 1 1 d . U . . .
D2 D 0.587(3) 0.8513(19) 1.060(3) 0.047 Uiso 1 1 d . U . . .
D3 D 0.175(3) 0.525(2) 0.962(3) 0.047 Uiso 1 1 d . U . . .
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'
D D 0.0000 0.0000 '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
_geom_angle_publ_flag
O1 C1 N1 126.33(18) . . ?
O1 C1 C2 125.33(17) . . ?
N1 C1 C2 108.32(16) . . ?
N2 C2 C1 112.03(15) . . ?
N2 C2 C7 104.51(15) . . ?
C1 C2 C7 105.32(14) . . ?
N2 C2 H4 111.5 . . ?
C1 C2 H4 111.5 . . ?
C7 C2 H4 111.5 . . ?
O2 C3 N2 126.19(17) . . ?
O2 C3 C4 125.26(17) . . ?
N2 C3 C4 108.54(16) . . ?
N3 C4 C3 111.70(15) . . ?
N3 C4 C7 104.36(14) . . ?
C3 C4 C7 105.16(14) . . ?
N3 C4 H3 111.7 . . ?
C3 C4 H3 111.7 . . ?
C7 C4 H3 111.7 . . ?
O3 C5 N3 126.01(18) . . ?
O3 C5 C6 124.60(17) . . ?
N3 C5 C6 109.37(16) . . ?
N1 C6 C5 110.30(15) . . ?
N1 C6 C7 104.42(14) . . ?
C5 C6 C7 104.72(15) . . ?
N1 C6 H2 112.3 . . ?
C5 C6 H2 112.3 . . ?
C7 C6 H2 112.3 . . ?
C4 C7 C2 106.05(14) . . ?
C4 C7 C6 106.57(14) . . ?
C2 C7 C6 106.17(15) . . ?
C4 C7 H1 112.5 . . ?
C2 C7 H1 112.5 . . ?
C6 C7 H1 112.5 . . ?
C1 N1 C6 115.71(16) . . ?
C1 N1 D2 123.5(14) . . ?
C6 N1 D2 120.0(14) . . ?
C3 N2 C2 115.51(16) . . ?
C3 N2 D3 122.4(17) . . ?
C2 N2 D3 122.1(17) . . ?
C5 N3 C4 114.93(16) . . ?
C5 N3 D1 122.6(16) . . ?
C4 N3 D1 122.3(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.220(2) . ?
C1 N1 1.343(2) . ?
C1 C2 1.522(3) . ?
C2 N2 1.451(2) . ?
C2 C7 1.534(2) . ?
C2 H4 0.9800 . ?
C3 O2 1.229(2) . ?
C3 N2 1.334(2) . ?
C3 C4 1.525(2) . ?
C4 N3 1.459(2) . ?
C4 C7 1.530(3) . ?
C4 H3 0.9800 . ?
C5 O3 1.231(2) . ?
C5 N3 1.337(2) . ?
C5 C6 1.516(2) . ?
C6 N1 1.448(2) . ?
C6 C7 1.536(2) . ?
C6 H2 0.9800 . ?
C7 H1 0.9800 . ?
N1 D2 0.91(2) . ?
N2 D3 0.82(2) . ?
N3 D1 0.85(2) . ?
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_site_symmetry_A
C2 H4 O1 0.98 2.45 3.097(2) 122.9 3_667
C4 H3 O1 0.98 2.59 3.157(2) 116.8 4_475
C6 H2 O1 0.98 2.51 3.302(2) 138.1 4_575
N3 D1 O1 0.85(2) 2.58(2) 3.036(2) 114.7(17) 4_475
N3 D1 O3 0.85(2) 2.21(2) 2.970(2) 149(2) 3_577
N1 D2 O3 0.91(2) 2.18(2) 2.908(2) 136.3(18) 3_677
N2 D3 O2 0.82(2) 2.18(2) 2.981(2) 166(2) 3_567
