#------------------------------------------------------------------------------
#$Date: 2020-12-06 10:37:34 +0200 (Sun, 06 Dec 2020) $
#$Revision: 259581 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241664.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_7241664
loop_
_publ_author_name
'Awatani, Ayano'
'Suzuki, Masaaki'
_publ_section_title
;
 Circular linkage of intramolecular multi-hydrogen bonding frameworks
 through nucleophilic substitutions of β-dicarbonyls onto cyanuric
 chloride and subsequent tautomerisation
;
_journal_issue                   64
_journal_name_full               'RSC Advances'
_journal_page_first              39033
_journal_page_last               39036
_journal_paper_doi               10.1039/D0RA07677E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C3.5 H3.5 N0.5 O1, C0.17 H0.67 O0.17 '
_chemical_formula_sum            'C3.67 H4.17 N0.5 O1.17'
_chemical_formula_weight         73.91
_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_Hall           '-P 6c'
_space_group_name_H-M_alt        'P 63/m'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   13.202(7)
_cell_length_b                   13.202(7)
_cell_length_c                   6.454(4)
_cell_measurement_reflns_used    628
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      72.9
_cell_measurement_theta_min      31.5
_cell_volume                     974.2(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            26405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         73.194
_diffrn_reflns_theta_min         3.866
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         707
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0502
_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)+(0.0450P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                581
_reflns_number_total             707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra07677e2.cif
_cod_data_source_block           91220su
_cod_original_cell_volume        974.2(12)
_cod_original_formula_sum        'C3.67 H4.17 N0.50 O1.17'
_cod_database_code               7241664
_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   0.797
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, x, z+1/2'
'y, -x+y, z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, -x, -z-1/2'
'-y, x-y, -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
N2 N 0.08840(14) 0.11049(14) 0.2500 0.0325(5) Uani 1 2 d S T P . .
H1 H 0.1466 0.1832 0.2500 0.039 Uiso 1 2 calc R U P . .
C7 C 0.11518(17) 0.02309(16) 0.2500 0.0323(5) Uani 1 2 d S T P . .
O3 O 0.17674(14) -0.15425(14) 0.2500 0.0490(5) Uani 1 2 d S T P A .
C8 C 0.23086(18) 0.04627(19) 0.2500 0.0372(5) Uani 1 2 d S T P A .
O4 O 0.31244(13) 0.25202(13) 0.2500 0.0472(5) Uani 1 2 d S T P A .
C11 C 0.2547(2) -0.0509(2) 0.2500 0.0456(6) Uani 1 2 d DS T P . .
C9 C 0.32762(19) 0.1673(2) 0.2500 0.0435(6) Uani 1 2 d DS T P . .
C12A C 0.3864(11) -0.0072(11) 0.225(3) 0.048(3) Uani 0.25 1 d D U P A -1
H6 H 0.4005 -0.0728 0.2540 0.058 Uiso 0.25 1 calc R U P A -1
H7 H 0.4094 0.0175 0.0799 0.058 Uiso 0.25 1 calc R U P A -1
C10A C 0.4492(13) 0.1835(16) 0.248(6) 0.052(2) Uani 0.25 1 d D U P A -1
H8 H 0.4717 0.1816 0.1021 0.062 Uiso 0.25 1 calc R U P A -1
H9 H 0.5043 0.2621 0.3037 0.062 Uiso 0.25 1 calc R U P A -1
C13 C 0.4635(18) 0.0947(14) 0.368(2) 0.049(3) Uani 0.25 1 d D U P A -1
H2 H 0.4319 0.0838 0.5108 0.059 Uiso 0.25 1 calc R U P A -1
H3 H 0.5456 0.1117 0.3721 0.059 Uiso 0.25 1 calc R U P A -1
O5 O 0.4440(7) -0.2257(9) 0.1848(16) 0.087(4) Uani 0.1667 1 d D U P B -1
H14 H 0.5001 -0.2384 0.1752 0.131 Uiso 0.1667 1 calc R U P B -1
C14 C 0.342(2) -0.329(3) 0.267(10) 0.076(7) Uani 0.1667 1 d D U P B -1
H15 H 0.3537 -0.3964 0.2544 0.113 Uiso 0.1667 1 calc R U P B -1
H16 H 0.2727 -0.3434 0.1888 0.113 Uiso 0.1667 1 calc R U P B -1
H17 H 0.3322 -0.3160 0.4133 0.113 Uiso 0.1667 1 calc R U P B -1
C12B C 0.3746(11) -0.0355(11) 0.276(3) 0.048(3) Uani 0.25 1 d D U P A -2
H10 H 0.3797 -0.0995 0.2056 0.058 Uiso 0.25 1 calc R U P A -2
H11 H 0.3930 -0.0356 0.4245 0.058 Uiso 0.25 1 calc R U P A -2
C10B C 0.4530(13) 0.1948(17) 0.207(3) 0.052(2) Uani 0.25 1 d D U P A -2
H12 H 0.5041 0.2403 0.3236 0.062 Uiso 0.25 1 calc R U P A -2
H13 H 0.4825 0.2433 0.0800 0.062 Uiso 0.25 1 calc R U P A -2
C15 C 0.4586(17) 0.0818(13) 0.177(2) 0.046(3) Uani 0.25 1 d D U P A -2
H4 H 0.4547 0.0677 0.0262 0.055 Uiso 0.25 1 calc R U P A -2
H5 H 0.5380 0.1006 0.2217 0.055 Uiso 0.25 1 calc R U P A -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 N2 C7 124.10(19) . 3 ?
C7 N2 H1 117.9 . . ?
C7 N2 H1 117.9 3 . ?
N2 C7 N2 115.90(19) . 4 ?
N2 C7 C8 122.04(17) . . ?
N2 C7 C8 122.06(17) 4 . ?
C7 C8 C9 119.99(19) . . ?
C7 C8 C11 119.79(19) . . ?
C9 C8 C11 120.22(19) . . ?
O3 C11 C8 122.97(19) . . ?
O3 C11 C12B 112.9(5) . . ?
C8 C11 C12B 123.7(5) . . ?
O3 C11 C12A 125.1(5) . . ?
C8 C11 C12A 111.6(6) . . ?
O4 C9 C8 122.82(19) . . ?
O4 C9 C10A 121.0(7) . . ?
C8 C9 C10A 116.1(7) . . ?
O4 C9 C10B 115.6(7) . . ?
C8 C9 C10B 120.5(7) . . ?
C13 C12A C11 113.4(14) . . ?
C13 C12A H6 108.9 . . ?
C11 C12A H6 108.9 . . ?
C13 C12A H7 108.9 . . ?
C11 C12A H7 108.9 . . ?
H6 C12A H7 107.7 . . ?
C13 C10A C9 115.2(19) . . ?
C13 C10A H8 108.5 . . ?
C9 C10A H8 108.5 . . ?
C13 C10A H9 108.5 . . ?
C9 C10A H9 108.5 . . ?
H8 C10A H9 107.5 . . ?
C10A C13 C12A 94.9(15) . . ?
C10A C13 H2 112.8 . . ?
C12A C13 H2 112.8 . . ?
C10A C13 H3 112.8 . . ?
C12A C13 H3 112.8 . . ?
H2 C13 H3 110.2 . . ?
C14 O5 H14 109.5 . . ?
O5 C14 H15 109.5 . . ?
O5 C14 H16 109.5 . . ?
H15 C14 H16 109.5 . . ?
O5 C14 H17 109.5 . . ?
H15 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C11 C12B C15 105.9(13) . . ?
C11 C12B H10 110.5 . . ?
C15 C12B H10 110.5 . . ?
C11 C12B H11 110.5 . . ?
C15 C12B H11 110.5 . . ?
H10 C12B H11 108.7 . . ?
C9 C10B C15 111.2(14) . . ?
C9 C10B H12 109.4 . . ?
C15 C10B H12 109.4 . . ?
C9 C10B H13 109.4 . . ?
C15 C10B H13 109.4 . . ?
H12 C10B H13 108.0 . . ?
C12B C15 C10B 124.8(15) . . ?
C12B C15 H4 106.1 . . ?
C10B C15 H4 106.1 . . ?
C12B C15 H5 106.1 . . ?
C10B C15 H5 106.1 . . ?
H4 C15 H5 106.3 . . ?
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
N2 C7 1.365(3) . ?
N2 C7 1.367(3) 3 ?
N2 H1 0.8800 . ?
C7 N2 1.367(3) 4 ?
C7 C8 1.400(3) . ?
O3 C11 1.232(3) . ?
C8 C9 1.464(3) . ?
C8 C11 1.465(3) . ?
O4 C9 1.231(3) . ?
C11 C12B 1.501(13) . ?
C11 C12A 1.543(13) . ?
C9 C10A 1.510(14) . ?
C9 C10B 1.533(14) . ?
C12A C13 1.526(15) . ?
C12A H6 0.9900 . ?
C12A H7 0.9900 . ?
C10A C13 1.497(19) . ?
C10A H8 0.9900 . ?
C10A H9 0.9900 . ?
C13 H2 0.9900 . ?
C13 H3 0.9900 . ?
O5 C14 1.451(11) . ?
O5 H14 0.8400 . ?
C14 H15 0.9800 . ?
C14 H16 0.9800 . ?
C14 H17 0.9800 . ?
C12B C15 1.521(14) . ?
C12B H10 0.9900 . ?
C12B H11 0.9900 . ?
C10B C15 1.542(17) . ?
C10B H12 0.9900 . ?
C10B H13 0.9900 . ?
C15 H4 0.9900 . ?
C15 H5 0.9900 . ?
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
N2 H1 O3 0.88 1.90 2.588(3) 133.6 3
N2 H1 O4 0.88 1.91 2.591(3) 133.5 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C7 N2 0.0 3 . . 4 ?
C7 N2 C7 C8 180.0 3 . . . ?
N2 C7 C8 C9 0.0 . . . . ?
N2 C7 C8 C9 180.0 4 . . . ?
N2 C7 C8 C11 180.0 . . . . ?
N2 C7 C8 C11 0.0 4 . . . ?
C7 C8 C11 O3 0.0 . . . . ?
C9 C8 C11 O3 180.0 . . . . ?
C7 C8 C11 C12B -172.3(10) . . . . ?
C9 C8 C11 C12B 7.7(10) . . . . ?
C7 C8 C11 C12A 173.6(9) . . . . ?
C9 C8 C11 C12A -6.4(9) . . . . ?
C7 C8 C9 O4 0.0 . . . . ?
C11 C8 C9 O4 180.0 . . . . ?
C7 C8 C9 C10A -179.4(18) . . . . ?
C11 C8 C9 C10A 0.6(18) . . . . ?
C7 C8 C9 C10B -167.8(8) . . . . ?
C11 C8 C9 C10B 12.2(8) . . . . ?
O3 C11 C12A C13 -139.1(10) . . . . ?
C8 C11 C12A C13 47.4(16) . . . . ?
O4 C9 C10A C13 144.9(14) . . . . ?
C8 C9 C10A C13 -36(3) . . . . ?
C9 C10A C13 C12A 67(3) . . . . ?
C11 C12A C13 C10A -74.3(19) . . . . ?
O3 C11 C12B C15 154.8(8) . . . . ?
C8 C11 C12B C15 -32.2(15) . . . . ?
O4 C9 C10B C15 -171.4(11) . . . . ?
C8 C9 C10B C15 -2.8(18) . . . . ?
C11 C12B C15 C10B 44(2) . . . . ?
C9 C10B C15 C12B -28(2) . . . . ?
