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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/36/7123669.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_7123669
loop_
_publ_author_name
'Bahili, Mohammed A.'
'Stokes, Emily C.'
'Amesbury, Robert C.'
'Ould, Darren M. C.'
'Christo, Bashar'
'Horne, Rhian J.'
'Kariuki, Benson M.'
'Stewart, Jack A.'
'Taylor, Rebekah L.'
'Williams, P. Andrew'
'Jones, Matthew D.'
'Harris, Kenneth D. M.'
'Ward, Benjamin D.'
_publ_section_title
;
 Aluminium-catalysed isocyanate trimerization, enhanced by exploiting a
 dynamic coordination sphere
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03339D
_journal_year                    2019
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-02-08 deposited with the CCDC.    2019-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.750(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.9239(11)
_cell_length_b                   5.4001(3)
_cell_length_c                   8.0430(6)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.6240
_cell_measurement_theta_min      3.9850
_cell_volume                     681.63(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5462
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_min         3.895
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       irregular
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0449
_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)+(0.0737P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1307
_reflns_number_total             1680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc03339d2.cif
_cod_data_source_block           4MeOC6H4NCO_dimer_monoclinic
_cod_database_code               7123669
_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   0.962
_shelx_estimated_absorpt_t_max   0.981
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
O1 O 0.48191(7) 0.1693(2) 0.64505(14) 0.0348(3) Uani 1 1 d . .
O2 O 0.89939(7) 0.5273(2) 0.85575(15) 0.0355(3) Uani 1 1 d . .
N1 N 0.56361(8) 0.4787(2) 0.52902(15) 0.0261(3) Uani 1 1 d . .
C1 C 0.49203(9) 0.3495(3) 0.56650(18) 0.0258(4) Uani 1 1 d . .
C2 C 0.64907(10) 0.4930(3) 0.60916(18) 0.0245(4) Uani 1 1 d . .
C3 C 0.68247(10) 0.3136(3) 0.7259(2) 0.0288(4) Uani 1 1 d . .
H3 H 0.6478 0.1803 0.7512 0.035 Uiso 1 1 calc R U
C4 C 0.76644(10) 0.3303(3) 0.8050(2) 0.0303(4) Uani 1 1 d . .
H4 H 0.7893 0.2085 0.8853 0.036 Uiso 1 1 calc R U
C5 C 0.81760(10) 0.5244(3) 0.76773(19) 0.0275(4) Uani 1 1 d . .
C6 C 0.78440(10) 0.7004(3) 0.6492(2) 0.0295(4) Uani 1 1 d . .
H6 H 0.8194 0.8319 0.6222 0.035 Uiso 1 1 calc R U
C7 C 0.70007(10) 0.6844(3) 0.5699(2) 0.0287(4) Uani 1 1 d . .
H7 H 0.6774 0.8051 0.4887 0.034 Uiso 1 1 calc R U
C8 C 0.95026(11) 0.7362(3) 0.8302(2) 0.0408(5) Uani 1 1 d . .
H8A H 0.9573 0.7433 0.7116 0.061 Uiso 1 1 calc R U
H8B H 1.0063 0.7213 0.9019 0.061 Uiso 1 1 calc R U
H8C H 0.9222 0.8877 0.8595 0.061 Uiso 1 1 calc R 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'
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
C5 O2 C8 116.60(12) . .
C2 N1 C1 133.08(12) . .
C2 N1 C1 132.92(12) . 3_666
C1 N1 C1 89.20(11) . 3_666
O1 C1 N1 134.97(14) . .
O1 C1 N1 134.23(14) . 3_666
N1 C1 N1 90.79(11) . 3_666
O1 C1 C1 179.46(17) . 3_666
N1 C1 C1 45.49(8) . 3_666
N1 C1 C1 45.30(8) 3_666 3_666
C7 C2 C3 120.15(14) . .
C7 C2 N1 119.76(13) . .
C3 C2 N1 120.09(13) . .
C4 C3 C2 119.65(14) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 120.40(14) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
O2 C5 C6 124.38(14) . .
O2 C5 C4 115.89(13) . .
C6 C5 C4 119.72(14) . .
C5 C6 C7 120.00(14) . .
C5 C6 H6 120.0 . .
C7 C6 H6 120.0 . .
C2 C7 C6 120.06(14) . .
C2 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
O2 C8 H8A 109.5 . .
O2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.1858(18) .
O2 C5 1.3731(18) .
O2 C8 1.424(2) .
N1 C2 1.4057(18) .
N1 C1 1.4119(18) .
N1 C1 1.4164(19) 3_666
C1 N1 1.4164(19) 3_666
C1 C1 1.986(3) 3_666
C2 C7 1.384(2) .
C2 C3 1.390(2) .
C3 C4 1.383(2) .
C3 H3 0.9500 .
C4 C5 1.391(2) .
C4 H4 0.9500 .
C5 C6 1.386(2) .
C6 C7 1.388(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350766
