#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/63/7056312.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_7056312
loop_
_publ_author_name
'Shopov, Dimitar Yavorov'
'Sharninghausen, Liam'
'Sinha, Shashi Bhushan'
'Borowski, Julia'
'Mercado, Brandon'
'Brudvig, Gary'
'Crabtree, Robert H.'
_publ_section_title
;
 Synthesis of Pyridine-Alkoxide Ligands for Formation of Polynuclear
 Complexes
;
_journal_issue                   14
_journal_name_full               'New J. Chem.'
_journal_page_first              6709
_journal_page_last               6719
_journal_paper_doi               10.1039/C7NJ01845B
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H25 N3 O3'
_chemical_formula_weight         379.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-18 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.002(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7376(14)
_cell_length_b                   12.3604(19)
_cell_length_c                   9.2476(14)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      3.3
_cell_volume                     949.9(3)
_computing_cell_refinement
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_data_collection
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_data_reduction
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_computing_molecular_graphics
; 
 Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
; 
Rigaku CrystalClear-SM Expert 2.0 r15 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_av_unetI/netI     0.0883
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11263
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.253
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
; 
 Flack x determined using 1011 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0980
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1570P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2348
_refine_ls_wR_factor_ref         0.2438
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2826
_reflns_number_total             3333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01845b2.cif
_cod_data_source_block           T3ligand
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'UNK' changed to 'unk'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        949.8(3)
_cod_database_code               7056312
#BEGIN Tags that were not found in dictionaries:
_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   0.982
_shelx_estimated_absorpt_t_max   0.991
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, 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 0.7927(7) 0.4400(5) 0.6686(6) 0.0351(14) Uani 1 1 d D .
H1 H 0.874(8) 0.480(6) 0.676(11) 0.04(3) Uiso 1 1 d D .
O2 O 0.6176(7) 0.2978(5) 0.7520(6) 0.0292(13) Uani 1 1 d D .
H2 H 0.698(10) 0.341(8) 0.767(15) 0.08(4) Uiso 1 1 d D .
O3 O 0.3960(7) 0.2157(5) 0.8714(6) 0.0330(14) Uani 1 1 d D .
H3 H 0.4791 0.2527 0.8803 0.050 Uiso 1 1 calc DR U
N1 N 0.5954(8) 0.4592(6) 0.2581(8) 0.0329(16) Uani 1 1 d . .
N2 N 0.4461(8) 0.2424(5) 0.3477(7) 0.0276(15) Uani 1 1 d . .
N3 N 0.3088(8) 0.0585(5) 0.5225(8) 0.0293(15) Uani 1 1 d . .
C1 C 0.6241(11) 0.4211(7) 0.1300(9) 0.034(2) Uani 1 1 d . .
H1A H 0.5487 0.4379 0.0341 0.040 Uiso 1 1 calc R U
C2 C 0.7533(11) 0.3612(7) 0.1323(9) 0.036(2) Uani 1 1 d . .
H2A H 0.7686 0.3373 0.0401 0.044 Uiso 1 1 calc R U
C3 C 0.8625(11) 0.3351(7) 0.2693(10) 0.035(2) Uani 1 1 d . .
H3A H 0.9541 0.2922 0.2739 0.043 Uiso 1 1 calc R U
C4 C 0.8366(10) 0.3731(6) 0.4038(9) 0.0258(17) Uani 1 1 d . .
H4 H 0.9125 0.3576 0.4999 0.031 Uiso 1 1 calc R U
C5 C 0.7022(10) 0.4323(6) 0.3952(9) 0.0262(17) Uani 1 1 d . .
C6 C 0.6580(11) 0.5980(7) 0.5300(11) 0.036(2) Uani 1 1 d . .
H6A H 0.7531 0.6270 0.5086 0.055 Uiso 1 1 calc R U
H6B H 0.6541 0.6257 0.6282 0.055 Uiso 1 1 calc R U
H6C H 0.5608 0.6205 0.4497 0.055 Uiso 1 1 calc R U
C7 C 0.6672(10) 0.4733(6) 0.5358(9) 0.0308(19) Uani 1 1 d . .
C8 C 0.5087(10) 0.4298(6) 0.5517(10) 0.0309(18) Uani 1 1 d . .
H8A H 0.4248 0.4379 0.4520 0.037 Uiso 1 1 calc R U
H8B H 0.4775 0.4770 0.6245 0.037 Uiso 1 1 calc R U
C9 C 0.5043(9) 0.3122(6) 0.6039(8) 0.0232(17) Uani 1 1 d . .
C10 C 0.3369(9) 0.2890(6) 0.6158(8) 0.0240(16) Uani 1 1 d . .
H10A H 0.2636 0.2767 0.5116 0.029 Uiso 1 1 calc R U
H10B H 0.2993 0.3551 0.6549 0.029 Uiso 1 1 calc R U
C11 C 0.3173(9) 0.1938(6) 0.7147(8) 0.0241(16) Uani 1 1 d . .
C12 C 0.1388(10) 0.1841(7) 0.7020(10) 0.0336(19) Uani 1 1 d . .
H12A H 0.1256 0.1301 0.7748 0.050 Uiso 1 1 calc R U
H12B H 0.0775 0.1618 0.5986 0.050 Uiso 1 1 calc R U
H12C H 0.0991 0.2543 0.7244 0.050 Uiso 1 1 calc R U
C13 C 0.4766(11) 0.1794(6) 0.2417(9) 0.0311(19) Uani 1 1 d . .
H13 H 0.4082 0.1847 0.1397 0.037 Uiso 1 1 calc R U
C14 C 0.6022(12) 0.1077(6) 0.2744(9) 0.035(2) Uani 1 1 d . .
H14 H 0.6212 0.0650 0.1962 0.042 Uiso 1 1 calc R U
C15 C 0.7000(11) 0.0984(6) 0.4216(10) 0.032(2) Uani 1 1 d . .
H15 H 0.7861 0.0479 0.4467 0.039 Uiso 1 1 calc R U
C16 C 0.6728(10) 0.1628(6) 0.5333(9) 0.0287(18) Uani 1 1 d . .
H16 H 0.7395 0.1579 0.6360 0.034 Uiso 1 1 calc R U
C17 C 0.5450(9) 0.2348(6) 0.4907(8) 0.0237(16) Uani 1 1 d . .
C18 C 0.3614(12) -0.0318(8) 0.4741(11) 0.041(2) Uani 1 1 d . .
H18 H 0.3147 -0.0521 0.3707 0.049 Uiso 1 1 calc R U
C19 C 0.4811(12) -0.0976(7) 0.5671(10) 0.036(2) Uani 1 1 d . .
H19 H 0.5205 -0.1586 0.5271 0.043 Uiso 1 1 calc R U
C20 C 0.5394(11) -0.0718(7) 0.7165(11) 0.039(2) Uani 1 1 d . .
H20 H 0.6155 -0.1177 0.7848 0.047 Uiso 1 1 calc R U
C21 C 0.4877(9) 0.0217(7) 0.7689(9) 0.0297(18) Uani 1 1 d . .
H21 H 0.5296 0.0410 0.8731 0.036 Uiso 1 1 calc R U
C22 C 0.3746(10) 0.0871(6) 0.6690(9) 0.0271(17) 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 0.0033 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
C7 O1 H1 108(7)
C9 O2 H2 112(9)
C11 O3 H3 109.5
C5 N1 C1 117.7(7)
C13 N2 C17 117.9(7)
C18 N3 C22 118.2(8)
C2 C1 N1 123.6(8)
C2 C1 H1A 118.2
N1 C1 H1A 118.2
C1 C2 C3 119.1(7)
C1 C2 H2A 120.5
C3 C2 H2A 120.5
C2 C3 C4 118.8(8)
C2 C3 H3A 120.6
C4 C3 H3A 120.6
C5 C4 C3 119.8(8)
C5 C4 H4 120.1
C3 C4 H4 120.1
N1 C5 C4 120.9(7)
N1 C5 C7 117.1(7)
C4 C5 C7 121.9(7)
C7 C6 H6A 109.5
C7 C6 H6B 109.5
H6A C6 H6B 109.5
C7 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
O1 C7 C5 109.7(6)
O1 C7 C8 106.9(6)
C5 C7 C8 113.2(6)
O1 C7 C6 109.6(7)
C5 C7 C6 109.1(6)
C8 C7 C6 108.3(7)
C7 C8 C9 118.2(7)
C7 C8 H8A 107.8
C9 C8 H8A 107.8
C7 C8 H8B 107.8
C9 C8 H8B 107.8
H8A C8 H8B 107.1
O2 C9 C10 107.6(6)
O2 C9 C8 110.0(6)
C10 C9 C8 108.5(6)
O2 C9 C17 109.7(6)
C10 C9 C17 111.1(6)
C8 C9 C17 110.0(6)
C9 C10 C11 118.3(6)
C9 C10 H10A 107.7
C11 C10 H10A 107.7
C9 C10 H10B 107.7
C11 C10 H10B 107.7
H10A C10 H10B 107.1
O3 C11 C22 110.6(6)
O3 C11 C12 104.7(6)
C22 C11 C12 109.1(6)
O3 C11 C10 110.7(6)
C22 C11 C10 113.2(6)
C12 C11 C10 108.2(6)
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
N2 C13 C14 122.7(8)
N2 C13 H13 118.6
C14 C13 H13 118.6
C15 C14 C13 119.0(7)
C15 C14 H14 120.5
C13 C14 H14 120.5
C14 C15 C16 119.8(8)
C14 C15 H15 120.1
C16 C15 H15 120.1
C17 C16 C15 117.8(8)
C17 C16 H16 121.1
C15 C16 H16 121.1
N2 C17 C16 122.8(7)
N2 C17 C9 114.4(6)
C16 C17 C9 122.7(7)
N3 C18 C19 123.5(9)
N3 C18 H18 118.3
C19 C18 H18 118.3
C20 C19 C18 117.8(8)
C20 C19 H19 121.1
C18 C19 H19 121.1
C19 C20 C21 119.6(8)
C19 C20 H20 120.2
C21 C20 H20 120.2
C22 C21 C20 119.9(8)
C22 C21 H21 120.1
C20 C21 H21 120.1
N3 C22 C21 120.8(8)
N3 C22 C11 115.7(7)
C21 C22 C11 123.4(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.431(10)
O1 H1 0.85(3)
O2 C9 1.432(9)
O2 H2 0.86(3)
O3 C11 1.425(9)
O3 H3 0.8400
N1 C5 1.364(10)
N1 C1 1.368(11)
N2 C13 1.342(10)
N2 C17 1.341(10)
N3 C18 1.336(12)
N3 C22 1.345(10)
C1 C2 1.345(13)
C1 H1A 0.9500
C2 C3 1.369(12)
C2 H2A 0.9500
C3 C4 1.412(11)
C3 H3A 0.9500
C4 C5 1.365(11)
C4 H4 0.9500
C5 C7 1.512(11)
C6 C7 1.543(11)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.535(11)
C8 C9 1.535(11)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.528(10)
C9 C17 1.539(11)
C10 C11 1.532(10)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C22 1.516(11)
C11 C12 1.532(11)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.370(13)
C13 H13 0.9500
C14 C15 1.370(13)
C14 H14 0.9500
C15 C16 1.382(11)
C15 H15 0.9500
C16 C17 1.387(11)
C16 H16 0.9500
C18 C19 1.393(14)
C18 H18 0.9500
C19 C20 1.355(13)
C19 H19 0.9500
C20 C21 1.381(12)
C20 H20 0.9500
C21 C22 1.386(11)
C21 H21 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.85(3) 1.99(5) 2.807(9) 160(9) 2_565
O2 H2 O1 0.86(3) 1.86(8) 2.598(8) 142(12) .
O3 H3 O2 0.84 2.02 2.706(8) 138.6 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177909
