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#$Date: 2023-03-04 20:24:48 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281477 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/61/7246122.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_7246122
loop_
_publ_author_name
'Das, Tamal Kanti'
'Rodriguez Treviño, Agustin M.'
'Pandiri, Sanjay'
'Irvankoski, Sini'
'Siitonen, Juha H.'
'Rodriguez, Sara M.'
'Yousufuddin, Muhammed'
'Kürti, László'
_publ_section_title
;
 Catalyst-free transfer hydrogenation of activated alkenes exploiting
 isopropanol as the sole and traceless reductant
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              746
_journal_page_last               754
_journal_paper_doi               10.1039/D2GC04315G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C13 H15 N O6'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc29zhqj
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.436(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.911(4)
_cell_length_b                   4.6748(7)
_cell_length_c                   23.299(4)
_cell_measurement_reflns_used    2128
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.71
_cell_volume                     2733.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13697
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.105
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0504
_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)+(0.0398P)²+2.2478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2507
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc04315g2.cif
_cod_data_source_block           tamal1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246122--7246123.cif.'
_cod_original_cell_volume        2733.1(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7246122
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.25079(6) 0.9388(3) 0.56471(6) 0.0386(4) Uani 1 1 d . . . . .
O2 O 0.27698(5) 1.0680(3) 0.65632(6) 0.0289(3) Uani 1 1 d . . . . .
O3 O 0.47994(5) 0.2365(3) 0.53522(5) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.51914(5) 0.6405(3) 0.57555(5) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.515505 0.686599 0.539914 0.033 Uiso 1 1 calc R U . . .
O5 O 0.56117(5) -0.0682(3) 0.70282(5) 0.0209(3) Uani 1 1 d . . . . .
O6 O 0.58933(5) 0.1475(3) 0.62956(5) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.28099(6) 0.9198(3) 0.61434(7) 0.0234(3) Uani 1 1 d . . . . .
C1 C 0.32476(6) 0.7111(4) 0.62333(7) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.33096(7) 0.5520(4) 0.57555(8) 0.0228(4) Uani 1 1 d . . . . .
H2A H 0.306933 0.572882 0.537656 0.027 Uiso 1 1 calc R U . . .
C3 C 0.37306(7) 0.3615(4) 0.58430(8) 0.0226(4) Uani 1 1 d . . . . .
H3 H 0.378025 0.250237 0.551971 0.027 Uiso 1 1 calc R U . . .
C4 C 0.40841(7) 0.3304(4) 0.64007(7) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.40008(7) 0.4931(4) 0.68691(7) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.423648 0.472163 0.725074 0.025 Uiso 1 1 calc R U . . .
C6 C 0.35834(7) 0.6845(4) 0.67921(8) 0.0205(4) Uani 1 1 d . . . . .
H6 H 0.352897 0.794698 0.711462 0.025 Uiso 1 1 calc R U . . .
C7 C 0.45558(7) 0.1313(4) 0.64884(8) 0.0239(4) Uani 1 1 d . . . . .
H7A H 0.446703 -0.027646 0.619978 0.029 Uiso 1 1 calc R U . . .
H7B H 0.462889 0.048115 0.689146 0.029 Uiso 1 1 calc R U . . .
C8 C 0.50503(6) 0.2812(4) 0.64113(7) 0.0185(4) Uani 1 1 d . . . . .
H8 H 0.510241 0.454621 0.667059 0.022 Uiso 1 1 calc R U . . .
C9 C 0.49999(6) 0.3831(4) 0.57828(7) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.55462(6) 0.0956(4) 0.66171(7) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.63840(7) -0.0247(4) 0.64099(8) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.631679 -0.217411 0.656316 0.029 Uiso 1 1 calc R U . . .
C12 C 0.68118(7) 0.1275(5) 0.68641(9) 0.0309(5) Uani 1 1 d . . . . .
H12A H 0.688829 0.312297 0.670480 0.046 Uiso 1 1 calc R U . . .
H12B H 0.713593 0.010573 0.695828 0.046 Uiso 1 1 calc R U . . .
H12C H 0.668928 0.158523 0.722465 0.046 Uiso 1 1 calc R U . . .
C13 C 0.65077(8) -0.0558(5) 0.58148(9) 0.0385(5) Uani 1 1 d . . . . .
H13A H 0.620784 -0.149231 0.553797 0.058 Uiso 1 1 calc R U . . .
H13B H 0.682950 -0.172226 0.585658 0.058 Uiso 1 1 calc R U . . .
H13C H 0.656615 0.133682 0.566270 0.058 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
_geom_angle_publ_flag
C9 O4 H4 109.5 . . ?
C10 O6 C11 118.27(13) . . ?
O2 N1 O1 123.41(16) . . ?
O2 N1 C1 118.54(15) . . ?
O1 N1 C1 118.05(15) . . ?
C6 C1 C2 122.65(16) . . ?
C6 C1 N1 118.47(16) . . ?
C2 C1 N1 118.87(15) . . ?
C1 C2 C3 118.29(16) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 C4 120.91(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.58(16) . . ?
C5 C4 C7 120.67(16) . . ?
C3 C4 C7 120.72(16) . . ?
C6 C5 C4 121.51(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 118.06(16) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 C8 112.36(15) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.94(14) . . ?
C7 C8 C10 111.84(14) . . ?
C9 C8 C10 110.23(13) . . ?
C7 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
C10 C8 H8 107.2 . . ?
O3 C9 O4 124.43(15) . . ?
O3 C9 C8 122.38(15) . . ?
O4 C9 C8 113.19(14) . . ?
O5 C10 O6 125.69(15) . . ?
O5 C10 C8 123.52(15) . . ?
O6 C10 C8 110.76(13) . . ?
O6 C11 C13 104.99(14) . . ?
O6 C11 C12 108.65(15) . . ?
C13 C11 C12 113.84(17) . . ?
O6 C11 H11 109.7 . . ?
C13 C11 H11 109.7 . . ?
C12 C11 H11 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 N1 1.2273(19) . ?
O2 N1 1.224(2) . ?
O3 C9 1.219(2) . ?
O4 C9 1.309(2) . ?
O4 H4 0.8400 . ?
O5 C10 1.205(2) . ?
O6 C10 1.329(2) . ?
O6 C11 1.472(2) . ?
N1 C1 1.471(2) . ?
C1 C6 1.379(2) . ?
C1 C2 1.381(2) . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C7 1.509(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.510(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(2) . ?
C8 C10 1.525(2) . ?
C8 H8 1.0000 . ?
C11 C13 1.506(3) . ?
C11 C12 1.507(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
