#------------------------------------------------------------------------------
#$Date: 2025-11-28 02:58:48 +0100 (Fri 28 de Nov de 2025) $
#$Revision: 303469 $
#$URL: svn://www.crystallography.net/cod/cif/3/00/06/3000605.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_3000605
loop_
_publ_author_name
'Bania, Ankur'
'Gogoi, Diptajyoti'
'Kalita, Nabadeep'
'Nakane, Takanori'
'Kawamoto, Akihiro'
'Althubeiti, Khaled'
'Sasaki, Toshiyuki'
'Kurisu, Genji'
'Thakuria, Ranjit'
_publ_section_title
;
 Beyond serendipity: uncovering novel ratiometric urea-24DHBA cocrystals
 through mechanochemistry and MicroED
;
_journal_name_full               'Chemical Communications'
_journal_page_first              16198
_journal_page_last               16201
_journal_paper_doi               10.1039/D5CC03628C
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C H4 N2 O), C7 H6 O4'
_chemical_formula_sum            'C9 H14 N4 O6'
_chemical_formula_weight         274.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                74.412(15)
_cell_angle_beta                 75.956(14)
_cell_angle_gamma                71.464(14)
_cell_formula_units_Z            2
_cell_length_a                   7.2558(10)
_cell_length_b                   8.8651(16)
_cell_length_c                   10.860(2)
_cell_measurement_reflns_used    8666
_cell_measurement_temperature    79
_cell_measurement_theta_max      1.1171058736815767
_cell_measurement_theta_min      0.13786914567765718
_cell_volume                     628.4(2)
_computing_cell_refinement
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       'SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      79
_diffrn_detector
;
Falcon 3 direct electron camera (integration mode)
;
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Talos Arctica electron microscope'
_diffrn_measurement_method
;
continuous rotation electron diffraction (MicroED)
;
_diffrn_radiation_probe          electron
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02508
_diffrn_reflns_av_R_equivalents  0.2278
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47366
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         0.984
_diffrn_reflns_theta_min         0.116
_diffrn_source                   'Talos Arctica Field Emission Gun'
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       powder
_exptl_crystal_F_000             99
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       21014(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1927
_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)+(0.1554P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4008
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2195
_reflns_number_total             3360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Urea-24DHBA-Pre.cif
_cod_data_source_block           urea-24dhba-pre
_cod_depositor_comments
;Releasing structure 3000605 into public domain as published material by
 including journal information.
;
_cod_database_code               3000605
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.05 and sigma for 1-3 distances of 0.05
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3)
4.b X=CH2 refined with riding coordinates:
 N14(H14A,H14B), N15(H15A,H15B), N18(H18A,H18B), N19(H19A,H19B)
4.c Idealised tetrahedral OH refined as rotating group:
 O11(H11), O9(H9), O10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N14 N 0.9506(7) 0.3173(7) -0.0175(5) 0.0263(13) Uani 1 1 d . . . . .
H14A H 0.843867 0.285049 0.020555 0.032 Uiso 1 1 calc R U . . .
H14B H 0.947883 0.394509 -0.088200 0.032 Uiso 1 1 calc R U . . .
N15 N 1.2803(7) 0.2961(7) -0.0289(5) 0.0256(13) Uani 1 1 d . . . . .
H15A H 1.391018 0.249467 0.002065 0.031 Uiso 1 1 calc R U . . .
H15B H 1.277000 0.373278 -0.099621 0.031 Uiso 1 1 calc R U . . .
O17 O 0.3884(7) 0.8035(7) 0.8816(5) 0.0285(13) Uani 1 1 d . . . . .
O11 O 0.5727(8) 0.4994(7) 0.8534(5) 0.0301(12) Uani 1 1 d . . . . .
H11 H 0.537711 0.600108 0.849911 0.045 Uiso 1 1 calc R U . . .
O13 O 1.1247(7) 0.1395(7) 0.1318(5) 0.0280(12) Uani 1 1 d . . . . .
N18 N 0.5221(8) 0.9987(7) 0.7429(6) 0.0355(16) Uani 1 1 d . . . . .
H18A H 0.640653 0.944226 0.760223 0.043 Uiso 1 1 calc R U . . .
H18B H 0.504923 1.092609 0.687245 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7355(9) 0.3085(8) 0.7226(6) 0.0243(14) Uani 1 1 d . . . . .
H5 H 0.739682 0.223950 0.798096 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6489(9) 0.4708(8) 0.7352(6) 0.0275(15) Uani 1 1 d . . . . .
O8 O 0.8863(8) 0.4628(7) 0.2620(5) 0.0316(13) Uani 1 1 d . . . . .
O9 O 0.9695(9) 0.2037(7) 0.3609(5) 0.0374(14) Uani 1 1 d . . . . .
H9 H 1.018740 0.192053 0.284444 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3688(8) 0.9389(7) 0.8007(6) 0.0220(14) Uani 1 1 d . . . . .
O10 O 0.7070(8) 0.6784(7) 0.3966(5) 0.0307(13) Uani 1 1 d . U . . .
H10 H 0.754307 0.639058 0.329782 0.046 Uiso 1 1 calc R U . . .
N19 N 0.1924(8) 1.0235(7) 0.7701(6) 0.0384(17) Uani 1 1 d . . . . .
H19A H 0.088977 0.985776 0.805884 0.046 Uiso 1 1 calc R U . . .
H19B H 0.179337 1.117131 0.714154 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8923(9) 0.3549(8) 0.3614(6) 0.0243(14) Uani 1 1 d . . . . .
C12 C 1.1162(9) 0.2492(8) 0.0317(6) 0.0253(14) Uani 1 1 d . U . . .
C2 C 0.7200(9) 0.5565(8) 0.5035(6) 0.0257(15) Uani 1 1 d . . . . .
C6 C 0.8139(9) 0.2705(8) 0.6036(6) 0.0263(15) Uani 1 1 d . . . . .
H6 H 0.872482 0.160022 0.597126 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6427(9) 0.5944(8) 0.6248(6) 0.0247(14) Uani 1 1 d . . . . .
H3 H 0.585586 0.704592 0.632348 0.030 Uiso 1 1 calc R U . . .
C1 C 0.8084(9) 0.3948(8) 0.4896(6) 0.0246(14) Uani 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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 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
H14A N14 H14B 120.0 . .
C12 N14 H14A 120.0 . .
C12 N14 H14B 120.0 . .
H15A N15 H15B 120.0 . .
C12 N15 H15A 120.0 . .
C12 N15 H15B 120.0 . .
C4 O11 H11 109.5 . .
H18A N18 H18B 120.0 . .
C16 N18 H18A 120.0 . .
C16 N18 H18B 120.0 . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C6 C5 C4 121.0(6) . .
O11 C4 C5 118.0(6) . .
O11 C4 C3 122.5(6) . .
C3 C4 C5 119.4(6) . .
C7 O9 H9 109.5 . .
O17 C16 N18 121.6(5) . .
O17 C16 N19 120.2(5) . .
N18 C16 N19 118.2(5) . .
C2 O10 H10 109.5 . .
C16 N19 H19A 120.0 . .
C16 N19 H19B 120.0 . .
H19A N19 H19B 120.0 . .
O8 C7 O9 123.5(7) . .
O8 C7 C1 120.8(6) . .
O9 C7 C1 115.7(5) . .
N14 C12 N15 119.7(5) . .
O13 C12 N14 121.5(5) . .
O13 C12 N15 118.8(5) . .
O10 C2 C3 119.0(6) . .
O10 C2 C1 119.7(6) . .
C3 C2 C1 121.3(6) . .
C5 C6 H6 119.8 . .
C5 C6 C1 120.4(6) . .
C1 C6 H6 119.8 . .
C4 C3 H3 120.1 . .
C2 C3 C4 119.9(6) . .
C2 C3 H3 120.1 . .
C2 C1 C7 121.3(5) . .
C2 C1 C6 118.0(6) . .
C6 C1 C7 120.7(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N14 H14A 0.8800 .
N14 H14B 0.8800 .
N14 C12 1.331(8) .
N15 H15A 0.8800 .
N15 H15B 0.8800 .
N15 C12 1.346(7) .
O17 C16 1.272(7) .
O11 H11 0.8400 .
O11 C4 1.326(9) .
O13 C12 1.248(7) .
N18 H18A 0.8800 .
N18 H18B 0.8800 .
N18 C16 1.330(8) .
C5 H5 0.9500 .
C5 C4 1.405(9) .
C5 C6 1.365(9) .
C4 C3 1.389(8) .
O8 C7 1.235(7) .
O9 H9 0.8400 .
O9 C7 1.279(9) .
C16 N19 1.331(8) .
O10 H10 0.8400 .
O10 C2 1.356(7) .
N19 H19A 0.8800 .
N19 H19B 0.8800 .
C7 C1 1.467(9) .
C2 C3 1.386(9) .
C2 C1 1.404(9) .
C6 H6 0.9500 .
C6 C1 1.419(8) .
C3 H3 0.9500 .
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
O11 C4 C3 C2 -178.2(6) . . . .
C5 C4 C3 C2 0.6(9) . . . .
C5 C6 C1 C7 180.0(6) . . . .
C5 C6 C1 C2 -0.1(9) . . . .
C4 C5 C6 C1 -0.3(9) . . . .
O8 C7 C1 C2 -0.5(9) . . . .
O8 C7 C1 C6 179.4(6) . . . .
O9 C7 C1 C2 179.7(6) . . . .
O9 C7 C1 C6 -0.4(9) . . . .
O10 C2 C3 C4 177.9(6) . . . .
O10 C2 C1 C7 1.7(9) . . . .
O10 C2 C1 C6 -178.2(5) . . . .
C6 C5 C4 O11 179.0(6) . . . .
C6 C5 C4 C3 0.1(9) . . . .
C3 C2 C1 C7 -179.3(5) . . . .
C3 C2 C1 C6 0.9(9) . . . .
C1 C2 C3 C4 -1.1(9) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
_cod_related_entry_description
1 XRDa 00390 DOI:10.51093/xrd-00390
