#------------------------------------------------------------------------------
#$Date: 2025-07-10 14:18:13 +0300 (Thu, 10 Jul 2025) $
#$Revision: 301209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573751.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_1573751
loop_
_publ_author_name
'Riu, Martin-Louis Y'
'Shan, Jing-Ran'
'Houk, K. N.'
'Nava, Matthew'
_publ_section_title
;
 Metal-ligand cooperativity enables zero-valent metal transfer.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              3888
_journal_page_last               3894
_journal_paper_doi               10.1039/d4sc07938h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C18 H36 In2 N2 O2'
_chemical_formula_weight         542.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V132 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-04-10 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4969(10)
_cell_length_b                   9.4605(5)
_cell_length_c                   18.0744(11)
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.93
_cell_volume                     2136.9(2)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-22 and APEX5 2023.9-2'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17176
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.254
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.071
_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     63
_refine_ls_number_reflns         1291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0203
_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)+(0.0141P)²+2.5073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1083
_reflns_number_total             1291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07938h2.cif
_cod_data_source_block           nava2402
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573748--1573752.cif.

2025-07-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C9 H18 In N O'
_cod_original_formula_weight         271.06
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               1573751
_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_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_file
;
TITL nava2402_a.res in Cmca
    nava2402_a.res
    created by SHELXL-2018/3 at 10:23:27 on 30-Jan-2024
REM Old TITL nava2402 in Cmca
REM SHELXT solution in Cmca: R1 0.101, Rweak 0.002, Alpha 0.020
REM <I/s>   0.595 for  111 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C9 In N O
CELL  0.71073  12.4969   9.4605  18.0744   90.000   90.000   90.000
ZERR    8.000   0.0010   0.0005   0.0011    0.000    0.000    0.000
LATT  7
SYMM -X, 1/2-Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM X, -Y, -Z
SFAC C H IN N O
UNIT 72 144 8 8 8
TEMP -173.150
L.S. 10
BOND
LIST 4
ACTA
FMAP 2
PLAN 20
WGHT    0.014100    2.507300
FVAR       0.22052
IN1   3    0.500000    0.625569    0.576093    10.50000    0.03580    0.01486 =
         0.01278   -0.00062    0.00000    0.00000
O1    5    0.500000    0.400271    0.549558    10.50000    0.02850    0.01397 =
         0.01056    0.00408    0.00000    0.00000
N1    4    0.500000    0.323099    0.619468    10.50000    0.01891    0.01432 =
         0.00898    0.00381    0.00000    0.00000
C1    1    0.397732    0.244626    0.626430    11.00000    0.01934    0.01927 =
         0.01477    0.00141   -0.00122   -0.00415
C2    1    0.309040    0.355361    0.631522    11.00000    0.01859    0.03125 =
         0.03179    0.00387   -0.00059    0.00126
AFIX 137
H2A   2    0.300956    0.402473    0.583558    11.00000   -1.50000
H2B   2    0.327690    0.425445    0.669309    11.00000   -1.50000
H2C   2    0.241585    0.309192    0.644964    11.00000   -1.50000
AFIX   0
C3    1    0.370557    0.143107    0.563209    11.00000    0.03665    0.02586 =
         0.02000    0.00320   -0.00778   -0.01205
AFIX 137
H3A   2    0.381970    0.190717    0.515706    11.00000   -1.50000
H3B   2    0.295524    0.113988    0.567225    11.00000   -1.50000
H3C   2    0.416781    0.059626    0.566225    11.00000   -1.50000
AFIX   0
C4    1    0.401470    0.164553    0.700382    11.00000    0.02314    0.02122 =
         0.01730    0.00306    0.00261   -0.00547
AFIX  23
H4A   2    0.400018    0.233755    0.741456    11.00000   -1.20000
H4B   2    0.336851    0.104573    0.704661    11.00000   -1.20000
AFIX   0
C5    1    0.500000    0.072368    0.708190    10.50000    0.03583    0.01791 =
         0.01374    0.00408    0.00000    0.00000
AFIX  23
H5A   2    0.500002    0.025453    0.757150    10.50000   -1.20000
H5B   2    0.499998   -0.001659    0.669475    10.50000   -1.20000
AFIX   0
HKLF 4




REM  nava2402_a.res in Cmca
REM wR2 = 0.0443, GooF = S = 1.035, Restrained GooF = 1.035 for all data
REM R1 = 0.0203 for 1083 Fo > 4sig(Fo) and 0.0283 for all 1291 data
REM 63 parameters refined using 0 restraints

END

WGHT      0.0141      2.5073

REM Highest difference peak  0.357,  deepest hole -0.422,  1-sigma level  0.071
Q1    1   0.3567  0.2930  0.6277  11.00000  0.05    0.36
Q2    1   0.4004  0.2038  0.6573  11.00000  0.05    0.33
Q3    1   0.3937  0.1992  0.6001  11.00000  0.05    0.29
Q4    1   0.4534  0.1212  0.7007  11.00000  0.05    0.28
Q5    1   0.4464  0.2726  0.6172  11.00000  0.05    0.27
Q6    1   0.6367  0.6316  0.6399  11.00000  0.05    0.27
Q7    1   0.5530  0.6161  0.5504  11.00000  0.05    0.26
Q8    1   0.5729  0.6601  0.6229  11.00000  0.05    0.24
Q9    1   0.1524  0.1588  0.5626  11.00000  0.05    0.21
Q10   1   0.3136  0.2795  0.7787  11.00000  0.05    0.20
Q11   1   0.4266  0.2158  0.7122  11.00000  0.05    0.20
Q12   1   0.3907  0.3134  0.4918  11.00000  0.05    0.20
Q13   1   0.2885  0.1305  0.7241  11.00000  0.05    0.20
Q14   1   0.4594  0.1543  0.5771  11.00000  0.05    0.20
Q15   1   0.4134  0.4078  0.5430  11.00000  0.05    0.20
Q16   1   0.2948  0.1392  0.4691  11.00000  0.05    0.19
Q17   1   0.1008  0.3058  0.6025  11.00000  0.05    0.19
Q18   1   0.3473  0.0202  0.5549  11.00000  0.05    0.19
Q19   1   0.2500  0.0001  0.7500  10.50000  0.05    0.19
Q20   1   0.5741  0.5701  0.5786  11.00000  0.05    0.19
;
_shelx_res_checksum              65030
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, 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
In1 In 0.500000 0.62557(2) 0.57609(2) 0.02115(8) Uani 1 2 d S T P . .
O1 O 0.500000 0.40027(19) 0.54956(11) 0.0177(4) Uani 1 2 d S T P . .
N1 N 0.500000 0.3231(2) 0.61947(12) 0.0141(5) Uani 1 2 d S T P . .
C1 C 0.39773(17) 0.2446(2) 0.62643(12) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.30904(18) 0.3554(2) 0.63152(14) 0.0272(5) Uani 1 1 d . . . . .
H2A H 0.300956 0.402473 0.583558 0.041 Uiso 1 1 calc R U . . .
H2B H 0.327690 0.425445 0.669309 0.041 Uiso 1 1 calc R U . . .
H2C H 0.241585 0.309192 0.644964 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3706(2) 0.1431(2) 0.56321(12) 0.0275(5) Uani 1 1 d . . . . .
H3A H 0.381970 0.190717 0.515706 0.041 Uiso 1 1 calc R U . . .
H3B H 0.295524 0.113988 0.567225 0.041 Uiso 1 1 calc R U . . .
H3C H 0.416781 0.059626 0.566225 0.041 Uiso 1 1 calc R U . . .
C4 C 0.40147(18) 0.1646(2) 0.70038(12) 0.0206(4) Uani 1 1 d . . . . .
H4A H 0.400018 0.233755 0.741456 0.025 Uiso 1 1 calc R U . . .
H4B H 0.336851 0.104573 0.704661 0.025 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.0724(3) 0.70819(16) 0.0225(7) Uani 1 2 d S T P . .
H5A H 0.500002 0.025453 0.757150 0.027 Uiso 1 2 calc R U P . .
H5B H 0.499998 -0.001659 0.669475 0.027 Uiso 1 2 calc R U P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
In1 0.03580(14) 0.01486(11) 0.01278(11) -0.00062(8) 0.000 0.000
O1 0.0285(12) 0.0140(9) 0.0106(9) 0.0041(7) 0.000 0.000
N1 0.0189(13) 0.0143(10) 0.0090(11) 0.0038(9) 0.000 0.000
C1 0.0193(11) 0.0193(9) 0.0148(9) 0.0014(8) -0.0012(9) -0.0042(8)
C2 0.0186(12) 0.0312(12) 0.0318(12) 0.0039(10) -0.0006(9) 0.0013(9)
C3 0.0366(14) 0.0259(11) 0.0200(11) 0.0032(9) -0.0078(9) -0.0120(10)
C4 0.0231(12) 0.0212(10) 0.0173(10) 0.0031(8) 0.0026(9) -0.0055(8)
C5 0.036(2) 0.0179(13) 0.0137(14) 0.0041(11) 0.000 0.000
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'
In In -0.7276 1.3100 '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
O1 In1 O1 71.18(8) . 9_666 ?
N1 O1 In1 107.34(14) . . ?
N1 O1 In1 143.84(15) . 9_666 ?
In1 O1 In1 108.83(8) . 9_666 ?
O1 N1 C1 108.89(13) . 12_655 ?
O1 N1 C1 108.90(13) . . ?
C1 N1 C1 119.0(2) 12_655 . ?
N1 C1 C2 106.68(17) . . ?
N1 C1 C3 116.22(19) . . ?
C2 C1 C3 108.31(19) . . ?
N1 C1 C4 107.11(18) . . ?
C2 C1 C4 107.91(18) . . ?
C3 C1 C4 110.28(17) . . ?
C5 C4 C1 112.91(19) . . ?
C4 C5 C4 108.7(2) 12_655 . ?
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
In1 O1 2.1847(19) . ?
In1 O1 2.284(2) 9_666 ?
O1 N1 1.459(3) . ?
N1 C1 1.483(2) 12_655 ?
N1 C1 1.483(2) . ?
C1 C2 1.528(3) . ?
C1 C3 1.531(3) . ?
C1 C4 1.537(3) . ?
C4 C5 1.515(3) . ?
