#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:19:52 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293059 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/12/1571242.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_1571242
loop_
_publ_author_name
'Gerz, Isabelle'
'Aunan, Erlend S.'
'Finelli, Valeria'
'Abu Rasheed, Mouhammad'
'Deplano, Gabriele'
'Cortez S P, Rafael'
'Schmidtke, Inga L.'
'Wragg, David S.'
'Signorile, Matteo'
'Hylland, Knut T.'
'Borfecchia, Elisa'
'Lillerud, Karl Petter'
'Bordiga, Silvia'
'Olsbye, Unni'
'Amedjkouh, Mohamed'
_publ_section_title
;
 Enabling a bioinspired N,N,N-copper coordination
 motif through spatial control in UiO-67: synthesis and reactivity.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8141
_journal_page_last               8153
_journal_paper_doi               10.1039/d3dt03096b
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         '2(Cl), C17 H16 N4 O4, 3(H2 O)'
_chemical_formula_sum            'C17 H22 Cl2 N4 O7'
_chemical_formula_weight         465.28
_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   mixed
_audit_creation_date             2021-08-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-26 deposited with the CCDC.	2024-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                111.8100(10)
_cell_angle_beta                 94.7840(10)
_cell_angle_gamma                97.0590(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4125(5)
_cell_length_b                   9.5825(5)
_cell_length_c                   12.6203(7)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.31
_cell_volume                     1038.46(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9312.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0460P)²+0.5320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4594
_reflns_number_total             5156
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03096b2.cif
_cod_data_source_block           mo_ig0247_0m_a
_cod_depositor_comments
'Adding full bibliography for 1571241--1571243.cif.'
_cod_database_code               1571242
_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.
;
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.869
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B), O6(H6A,H6B), O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4A), C5(H5), C4(H4B), C2(H2A), C9(H9), C8(H8), C11(H11)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_date_sample_data_collection 2021-08-25
_olex2_date_sample_submission    2021-08-16
_olex2_exptl_crystal_mounting_method
'Frozen on a Mitegen cryoloop using Paretone oil.'
_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
Cl1 Cl 0.73035(3) -0.31882(3) 0.47493(3) 0.01774(8) Uani 1 1 d . . . . .
Cl2 Cl 1.00419(3) 1.57043(4) 0.77652(3) 0.01969(9) Uani 1 1 d . . . . .
O1 O 0.25856(10) 1.10238(11) 0.92077(9) 0.0190(2) Uani 1 1 d . . . . .
H1 H 0.241096 1.189650 0.958836 0.028 Uiso 1 1 calc R U . . .
O4 O 0.63837(12) -0.01148(11) 0.59169(9) 0.0226(2) Uani 1 1 d . . . . .
H4 H 0.666898 -0.094442 0.557892 0.034 Uiso 1 1 calc R U . . .
O2 O 0.47745(11) 1.23277(11) 0.93609(9) 0.0208(2) Uani 1 1 d . . . . .
O7 O 1.04955(11) 0.69549(11) 0.58257(9) 0.0215(2) Uani 1 1 d G . . . .
H7A H 1.039358 0.645231 0.627147 0.032 Uiso 1 1 d G U . . .
H7B H 0.968132 0.667400 0.536445 0.032 Uiso 1 1 d G U . . .
O6 O 0.24321(12) 1.61819(13) 0.98556(10) 0.0264(2) Uani 1 1 d G . . . .
H6A H 0.329991 1.666018 0.991157 0.040 Uiso 1 1 d G U . . .
H6B H 0.198084 1.617036 0.922153 0.040 Uiso 1 1 d G U . . .
O5 O 0.19142(13) 1.36296(12) 1.02712(11) 0.0310(3) Uani 1 1 d G . . . .
H5A H 0.210156 1.442091 1.009300 0.047 Uiso 1 1 d G U . . .
H5B H 0.129637 1.387229 1.075864 0.047 Uiso 1 1 d G U . . .
N1 N 0.64715(12) 0.49038(12) 0.61532(10) 0.0153(2) Uani 1 1 d . . . . .
N2 N 0.78339(12) 0.81269(12) 0.78696(10) 0.0158(2) Uani 1 1 d . . . . .
O3 O 0.74721(16) 0.05806(13) 0.46423(13) 0.0455(4) Uani 1 1 d . . . . .
N3 N 1.01627(12) 0.99763(13) 0.69555(10) 0.0179(2) Uani 1 1 d . . . . .
H3 H 1.038492 0.906280 0.661730 0.021 Uiso 1 1 calc R U . . .
N4 N 0.99784(13) 1.23219(13) 0.73552(11) 0.0222(3) Uani 1 1 d . . . . .
H4A H 1.005684 1.323165 0.732688 0.027 Uiso 1 1 calc R U . . .
C1 C 0.63863(13) 0.81832(14) 0.79376(11) 0.0135(2) Uani 1 1 d . . . . .
C3 C 0.44221(14) 0.96057(14) 0.85138(11) 0.0137(2) Uani 1 1 d . . . . .
C5 C 0.39030(14) 0.68869(15) 0.76471(11) 0.0161(2) Uani 1 1 d . . . . .
H5 H 0.322792 0.596535 0.738108 0.019 Uiso 1 1 calc R U . . .
C12 C 0.39595(14) 1.11175(14) 0.90689(11) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.34222(14) 0.82676(15) 0.81260(11) 0.0159(2) Uani 1 1 d . . . . .
H4B H 0.242663 0.829882 0.818801 0.019 Uiso 1 1 calc R U . . .
C7 C 0.57747(13) 0.52969(14) 0.70893(11) 0.0139(2) Uani 1 1 d . . . . .
C2 C 0.58804(13) 0.95713(14) 0.84112(11) 0.0137(2) Uani 1 1 d . . . . .
H2A H 0.654167 1.050137 0.866576 0.016 Uiso 1 1 calc R U . . .
C15 C 0.94011(14) 1.04182(15) 0.78872(11) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.57546(15) 0.27676(15) 0.70414(12) 0.0177(3) Uani 1 1 d . . . . .
H9 H 0.550318 0.202180 0.735196 0.021 Uiso 1 1 calc R U . . .
C10 C 0.64500(14) 0.24076(14) 0.60719(12) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.53605(14) 0.68269(14) 0.75490(11) 0.0136(2) Uani 1 1 d . . . . .
C8 C 0.54268(15) 0.42208(15) 0.75566(11) 0.0174(3) Uani 1 1 d . . . . .
H8 H 0.496449 0.447794 0.822882 0.021 Uiso 1 1 calc R U . . .
C11 C 0.68171(14) 0.35130(15) 0.56388(12) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.730967 0.329020 0.498301 0.021 Uiso 1 1 calc R U . . .
C14 C 0.89617(14) 0.94193(15) 0.85132(12) 0.0171(3) Uani 1 1 d . . . . .
H14A H 0.982383 0.903413 0.872877 0.020 Uiso 1 1 calc R U . . .
H14B H 0.862472 1.004559 0.923543 0.020 Uiso 1 1 calc R U . . .
C16 C 0.92923(15) 1.18939(16) 0.81324(12) 0.0197(3) Uani 1 1 d . . . . .
C17 C 1.05039(16) 1.11512(16) 0.66543(13) 0.0225(3) Uani 1 1 d . . . . .
C13 C 0.68337(15) 0.08638(15) 0.54598(13) 0.0201(3) Uani 1 1 d . . . . .
H16 H 0.886(2) 1.260(2) 0.8751(16) 0.026(5) Uiso 1 1 d . . . . .
H17 H 1.106(2) 1.119(2) 0.6069(17) 0.032(5) Uiso 1 1 d . . . . .
H2 H 0.810(2) 0.725(2) 0.7725(16) 0.028(5) Uiso 1 1 d . . . . .
H1A H 0.671(2) 0.564(2) 0.5828(17) 0.034(5) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C12 O1 H1 109.5 . . ?
C13 O4 H4 109.5 . . ?
H7A O7 H7B 104.5 . . ?
H6A O6 H6B 104.5 . . ?
H5A O5 H5B 104.5 . . ?
C7 N1 H1A 118.5(12) . . ?
C11 N1 C7 123.31(11) . . ?
C11 N1 H1A 118.1(12) . . ?
C1 N2 C14 122.69(11) . . ?
C1 N2 H2 116.9(13) . . ?
C14 N2 H2 114.1(13) . . ?
C15 N3 H3 125.4 . . ?
C17 N3 H3 125.4 . . ?
C17 N3 C15 109.15(11) . . ?
C16 N4 H4A 125.3 . . ?
C17 N4 H4A 125.3 . . ?
C17 N4 C16 109.40(12) . . ?
N2 C1 C2 121.66(11) . . ?
N2 C1 C6 120.66(11) . . ?
C2 C1 C6 117.66(11) . . ?
C4 C3 C12 120.64(11) . . ?
C4 C3 C2 120.97(11) . . ?
C2 C3 C12 118.39(11) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.12(12) . . ?
C6 C5 H5 119.4 . . ?
O1 C12 C3 113.76(11) . . ?
O2 C12 O1 122.99(12) . . ?
O2 C12 C3 123.24(12) . . ?
C3 C4 H4B 120.6 . . ?
C5 C4 C3 118.80(12) . . ?
C5 C4 H4B 120.6 . . ?
N1 C7 C6 119.22(11) . . ?
N1 C7 C8 118.36(11) . . ?
C8 C7 C6 122.37(11) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 120.92(11) . . ?
C3 C2 H2A 119.5 . . ?
N3 C15 C14 123.38(11) . . ?
C16 C15 N3 106.40(12) . . ?
C16 C15 C14 129.95(13) . . ?
C10 C9 H9 120.1 . . ?
C10 C9 C8 119.75(12) . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C13 123.11(12) . . ?
C11 C10 C9 119.23(12) . . ?
C11 C10 C13 117.66(12) . . ?
C1 C6 C7 122.52(11) . . ?
C5 C6 C1 120.51(11) . . ?
C5 C6 C7 116.88(11) . . ?
C7 C8 C9 119.89(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N1 C11 C10 119.42(12) . . ?
N1 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N2 C14 C15 114.87(11) . . ?
N2 C14 H14A 108.5 . . ?
N2 C14 H14B 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
N4 C16 H16 122.8(11) . . ?
C15 C16 N4 107.14(12) . . ?
C15 C16 H16 130.0(11) . . ?
N3 C17 H17 127.5(12) . . ?
N4 C17 N3 107.90(13) . . ?
N4 C17 H17 124.6(12) . . ?
O4 C13 C10 112.53(12) . . ?
O3 C13 O4 125.06(13) . . ?
O3 C13 C10 122.40(13) . . ?
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
O1 H1 0.8400 . ?
O1 C12 1.3161(15) . ?
O4 H4 0.8400 . ?
O4 C13 1.3178(17) . ?
O2 C12 1.2188(16) . ?
O7 H7A 0.8698 . ?
O7 H7B 0.8701 . ?
O6 H6A 0.8698 . ?
O6 H6B 0.8697 . ?
O5 H5A 0.8701 . ?
O5 H5B 0.8702 . ?
N1 C7 1.3517(17) . ?
N1 C11 1.3425(16) . ?
N1 H1A 0.95(2) . ?
N2 C1 1.3788(16) . ?
N2 C14 1.4512(17) . ?
N2 H2 0.87(2) . ?
O3 C13 1.1978(19) . ?
N3 H3 0.8800 . ?
N3 C15 1.3860(17) . ?
N3 C17 1.3284(18) . ?
N4 H4A 0.8800 . ?
N4 C16 1.3737(19) . ?
N4 C17 1.3257(18) . ?
C1 C2 1.4020(17) . ?
C1 C6 1.4145(17) . ?
C3 C12 1.4936(17) . ?
C3 C4 1.3892(18) . ?
C3 C2 1.3927(17) . ?
C5 H5 0.9500 . ?
C5 C4 1.3854(17) . ?
C5 C6 1.3939(18) . ?
C4 H4B 0.9500 . ?
C7 C6 1.4779(17) . ?
C7 C8 1.3855(18) . ?
C2 H2A 0.9500 . ?
C15 C14 1.4935(19) . ?
C15 C16 1.3496(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3855(19) . ?
C9 C8 1.3868(18) . ?
C10 C11 1.3827(19) . ?
C10 C13 1.4982(18) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16 0.980(19) . ?
C17 H17 0.95(2) . ?
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
N1 C7 C6 C1 -59.54(17) . . . . ?
N1 C7 C6 C5 123.96(13) . . . . ?
N1 C7 C8 C9 -1.99(19) . . . . ?
N2 C1 C2 C3 -177.51(12) . . . . ?
N2 C1 C6 C5 178.29(12) . . . . ?
N2 C1 C6 C7 1.91(19) . . . . ?
N3 C15 C14 N2 -70.31(16) . . . . ?
N3 C15 C16 N4 0.10(15) . . . . ?
C1 N2 C14 C15 -92.25(15) . . . . ?
C12 C3 C4 C5 -178.11(12) . . . . ?
C12 C3 C2 C1 177.58(11) . . . . ?
C4 C3 C12 O1 4.16(17) . . . . ?
C4 C3 C12 O2 -175.45(13) . . . . ?
C4 C3 C2 C1 -1.48(19) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 176.50(12) . . . . ?
C7 N1 C11 C10 0.1(2) . . . . ?
C2 C1 C6 C5 -0.45(18) . . . . ?
C2 C1 C6 C7 -176.82(11) . . . . ?
C2 C3 C12 O1 -174.90(11) . . . . ?
C2 C3 C12 O2 5.50(19) . . . . ?
C2 C3 C4 C5 0.92(19) . . . . ?
C15 N3 C17 N4 -0.43(16) . . . . ?
C9 C10 C11 N1 -1.1(2) . . . . ?
C9 C10 C13 O4 2.65(19) . . . . ?
C9 C10 C13 O3 -177.79(16) . . . . ?
C10 C9 C8 C7 1.0(2) . . . . ?
C6 C1 C2 C3 1.21(18) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C6 C7 C8 C9 175.52(12) . . . . ?
C8 C7 C6 C1 122.97(14) . . . . ?
C8 C7 C6 C5 -53.53(17) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C8 C9 C10 C13 -179.59(13) . . . . ?
C11 N1 C7 C6 -176.17(12) . . . . ?
C11 N1 C7 C8 1.42(19) . . . . ?
C11 C10 C13 O4 -177.47(12) . . . . ?
C11 C10 C13 O3 2.1(2) . . . . ?
C14 N2 C1 C2 15.26(19) . . . . ?
C14 N2 C1 C6 -163.42(12) . . . . ?
C14 C15 C16 N4 174.23(13) . . . . ?
C16 N4 C17 N3 0.50(17) . . . . ?
C16 C15 C14 N2 116.44(16) . . . . ?
C17 N3 C15 C14 -174.41(13) . . . . ?
C17 N3 C15 C16 0.20(16) . . . . ?
C17 N4 C16 C15 -0.37(17) . . . . ?
C13 C10 C11 N1 178.98(12) . . . . ?
