#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:18:11 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296631 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063501.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_7063501
loop_
_publ_author_name
'Smirnova, Ksenia S.'
'Sanzhenakova, Elizaveta A.'
'Eltsov, Ilia V.'
'Pozdnyakov, Ivan P.'
'Russkikh, Alena A.'
'Dotsenko, Victor V.'
'Lider, Elizaveta V.'
_publ_section_title
;
 Photoluminescent lanthanide(iii) coordination polymers based on
 2-{[(4-methylphenyl)amino]methylene}-5,5-dimethylcyclohexane-1,3-dione
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18536
_journal_page_last               18545
_journal_paper_doi               10.1039/D4NJ03444A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-09-30 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.245(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8139(10)
_cell_length_b                   5.8067(4)
_cell_length_c                   20.3464(13)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.44
_cell_volume                     1373.50(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.527
_diffrn_reflns_theta_min         2.034
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.9229.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0580
_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)+(0.0579P)²+0.4277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2911
_reflns_number_total             4583
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj03444a2.cif
_cod_data_source_block           20ypp
_cod_depositor_comments
'Adding full bibliography for 7063497--7063502.cif.'
_cod_original_cell_volume        1373.51(17)
_cod_database_code               7063501
_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_max   0.997
_shelx_estimated_absorpt_t_min   0.990
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C9(H9), C11(H11), C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C14(H14A,H14B,H14C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85127(10) 1.0670(2) 0.55589(6) 0.0398(3) Uani 1 1 d . . . . .
N1 N 0.79945(10) 0.6925(2) 0.48060(6) 0.0296(3) Uani 1 1 d . . . . .
H1 H 0.8495 0.8029 0.4935 0.036 Uiso 1 1 calc R U . . .
O2 O 0.49834(11) 0.6917(3) 0.55090(8) 0.0645(5) Uani 1 1 d . . . . .
C8 C 0.67668(12) 0.8669(3) 0.54880(7) 0.0286(3) Uani 1 1 d . . . . .
C10 C 0.83196(12) 0.5246(3) 0.43663(7) 0.0276(3) Uani 1 1 d . . . . .
C13 C 0.90746(12) 0.2037(3) 0.35099(7) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.75577(13) 1.0504(3) 0.57318(7) 0.0301(3) Uani 1 1 d . . . . .
C12 C 0.80192(13) 0.1783(3) 0.37168(7) 0.0317(3) Uani 1 1 d . . . . .
H12 H 0.7550 0.0494 0.3565 0.038 Uiso 1 1 calc R U . . .
C3 C 0.64033(13) 1.1277(3) 0.66535(7) 0.0303(3) Uani 1 1 d . . . . .
C9 C 0.70273(12) 0.7010(3) 0.50413(7) 0.0293(3) Uani 1 1 d . . . . .
H9 H 0.6466 0.5861 0.4897 0.035 Uiso 1 1 calc R U . . .
C11 C 0.76334(13) 0.3362(3) 0.41389(7) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.6908 0.3158 0.4271 0.038 Uiso 1 1 calc R U . . .
C16 C 0.93816(13) 0.5517(3) 0.41758(7) 0.0319(3) Uani 1 1 d . . . . .
H16 H 0.9857 0.6791 0.4335 0.038 Uiso 1 1 calc R U . . .
C15 C 0.97453(13) 0.3921(3) 0.37526(8) 0.0339(3) Uani 1 1 d . . . . .
H15 H 1.0474 0.4120 0.3625 0.041 Uiso 1 1 calc R U . . .
C7 C 0.56714(13) 0.8455(3) 0.57096(8) 0.0348(3) Uani 1 1 d . . . . .
C4 C 0.70430(14) 0.9488(3) 0.71341(8) 0.0352(4) Uani 1 1 d . . . . .
H4A H 0.7303 0.8226 0.6878 0.053 Uiso 1 1 calc R U . . .
H4B H 0.6526 0.8881 0.7419 0.053 Uiso 1 1 calc R U . . .
H4C H 0.7710 1.0212 0.7413 0.053 Uiso 1 1 calc R U . . .
C2 C 0.71979(15) 1.2236(3) 0.62041(8) 0.0366(4) Uani 1 1 d . . . . .
H2A H 0.6803 1.3528 0.5940 0.044 Uiso 1 1 calc R U . . .
H2B H 0.7896 1.2864 0.6489 0.044 Uiso 1 1 calc R U . . .
C6 C 0.53694(13) 1.0189(3) 0.61995(8) 0.0353(3) Uani 1 1 d . . . . .
H6A H 0.4881 0.9427 0.6483 0.042 Uiso 1 1 calc R U . . .
H6B H 0.4908 1.1430 0.5948 0.042 Uiso 1 1 calc R U . . .
C14 C 0.94647(15) 0.0336(3) 0.30383(8) 0.0387(4) Uani 1 1 d . . . . .
H14A H 0.8868 -0.0834 0.2913 0.058 Uiso 1 1 calc R U . . .
H14B H 1.0177 -0.0407 0.3258 0.058 Uiso 1 1 calc R U . . .
H14C H 0.9604 0.1142 0.2637 0.058 Uiso 1 1 calc R U . . .
C5 C 0.59820(16) 1.3219(3) 0.70562(9) 0.0431(4) Uani 1 1 d . . . . .
H5A H 0.5463 1.2587 0.7336 0.065 Uiso 1 1 calc R U . . .
H5B H 0.5571 1.4367 0.6750 0.065 Uiso 1 1 calc R U . . .
H5C H 0.6642 1.3947 0.7340 0.065 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
C10 N1 H1 116.4 . . ?
C9 N1 H1 116.4 . . ?
C9 N1 C10 127.17(13) . . ?
C1 C8 C7 120.99(13) . . ?
C9 C8 C1 121.89(14) . . ?
C9 C8 C7 117.12(13) . . ?
C11 C10 N1 122.82(13) . . ?
C16 C10 N1 117.21(13) . . ?
C16 C10 C11 119.95(14) . . ?
C12 C13 C14 121.01(14) . . ?
C15 C13 C12 117.43(14) . . ?
C15 C13 C14 121.56(14) . . ?
O1 C1 C8 121.56(14) . . ?
O1 C1 C2 120.19(13) . . ?
C8 C1 C2 118.25(13) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 C13 121.84(14) . . ?
C11 C12 H12 119.1 . . ?
C2 C3 C4 110.10(13) . . ?
C2 C3 C6 107.38(12) . . ?
C2 C3 C5 110.21(13) . . ?
C6 C3 C4 110.83(13) . . ?
C5 C3 C4 109.21(13) . . ?
C5 C3 C6 109.09(13) . . ?
N1 C9 C8 124.69(13) . . ?
N1 C9 H9 117.7 . . ?
C8 C9 H9 117.7 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.30(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C16 H16 120.2 . . ?
C15 C16 C10 119.61(14) . . ?
C15 C16 H16 120.2 . . ?
C13 C15 H15 119.1 . . ?
C16 C15 C13 121.86(14) . . ?
C16 C15 H15 119.1 . . ?
O2 C7 C8 122.27(15) . . ?
O2 C7 C6 119.11(14) . . ?
C8 C7 C6 118.63(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C2 C3 114.36(12) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C3 C6 H6A 108.6 . . ?
C3 C6 H6B 108.6 . . ?
C7 C6 C3 114.74(13) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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 C1 1.2438(18) . ?
N1 H1 0.8800 . ?
N1 C10 1.4215(19) . ?
N1 C9 1.3161(18) . ?
O2 C7 1.2276(19) . ?
C8 C1 1.445(2) . ?
C8 C9 1.396(2) . ?
C8 C7 1.449(2) . ?
C10 C11 1.391(2) . ?
C10 C16 1.386(2) . ?
C13 C12 1.393(2) . ?
C13 C15 1.389(2) . ?
C13 C14 1.505(2) . ?
C1 C2 1.504(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(2) . ?
C3 C4 1.531(2) . ?
C3 C2 1.527(2) . ?
C3 C6 1.531(2) . ?
C3 C5 1.528(2) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.385(2) . ?
C15 H15 0.9500 . ?
C7 C6 1.503(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
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
O1 C1 C2 C3 -149.01(14) . . . . ?
N1 C10 C11 C12 -179.21(13) . . . . ?
N1 C10 C16 C15 179.47(13) . . . . ?
O2 C7 C6 C3 153.07(17) . . . . ?
C8 C1 C2 C3 31.09(19) . . . . ?
C8 C7 C6 C3 -27.2(2) . . . . ?
C10 N1 C9 C8 178.10(13) . . . . ?
C10 C16 C15 C13 0.0(2) . . . . ?
C13 C12 C11 C10 -0.4(2) . . . . ?
C1 C8 C9 N1 0.7(2) . . . . ?
C1 C8 C7 O2 179.81(16) . . . . ?
C1 C8 C7 C6 0.1(2) . . . . ?
C12 C13 C15 C16 -1.0(2) . . . . ?
C9 N1 C10 C11 -2.2(2) . . . . ?
C9 N1 C10 C16 179.18(14) . . . . ?
C9 C8 C1 O1 -0.8(2) . . . . ?
C9 C8 C1 C2 179.11(13) . . . . ?
C9 C8 C7 O2 -1.3(2) . . . . ?
C9 C8 C7 C6 179.02(14) . . . . ?
C11 C10 C16 C15 0.8(2) . . . . ?
C16 C10 C11 C12 -0.6(2) . . . . ?
C15 C13 C12 C11 1.2(2) . . . . ?
C7 C8 C1 O1 178.07(14) . . . . ?
C7 C8 C1 C2 -2.0(2) . . . . ?
C7 C8 C9 N1 -178.22(14) . . . . ?
C4 C3 C2 C1 65.78(16) . . . . ?
C4 C3 C6 C7 -67.27(18) . . . . ?
C2 C3 C6 C7 53.02(18) . . . . ?
C6 C3 C2 C1 -54.97(17) . . . . ?
C14 C13 C12 C11 -178.50(14) . . . . ?
C14 C13 C15 C16 178.68(14) . . . . ?
C5 C3 C2 C1 -173.68(13) . . . . ?
C5 C3 C6 C7 172.45(14) . . . . ?
