#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:41:23 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127140.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_7127140
loop_
_publ_author_name
'Jaoul, Arnaud'
'Yang, Yan'
'Casaretto, Nicolas'
'Clavaguéra, Carine'
'Maron, Laurent'
'Nocton, Grégory'
_publ_section_title
;
 Atom economical coupling of benzophenone and N-heterocyclic aromatics
 with SmI₂.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11875
_journal_page_last               11878
_journal_paper_doi               10.1039/d0cc05164k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_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             2020-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.749(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1307(4)
_cell_length_b                   14.6655(8)
_cell_length_c                   11.5353(6)
_cell_measurement_reflns_used    2366
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      29.1508
_cell_measurement_theta_min      2.5177
_cell_volume                     1368.56(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    SHELXT(Sheldrick,2014)
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8115
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.693
_diffrn_reflns_theta_min         2.253
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0523 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.9184.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0456
_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)+(0.0493P)²+0.3039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2635
_reflns_number_total             3462
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05164k2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7127135--7127141.cif.'
_cod_database_code               7127140
_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   0.992
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.b Tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
C1 C 0.38172(14) 0.03750(9) 0.25625(10) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.34367(15) 0.12579(9) 0.18740(11) 0.0244(3) Uani 1 1 d . . . . .
C3 C 0.43247(16) 0.15261(10) 0.09582(12) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.523110 0.116795 0.076362 0.037 Uiso 1 1 calc R U . . .
C4 C 0.38962(18) 0.23107(10) 0.03294(13) 0.0365(3) Uani 1 1 d . . . . .
H4 H 0.450257 0.248465 -0.029752 0.044 Uiso 1 1 calc R U . . .
C5 C 0.25885(19) 0.28408(10) 0.06125(13) 0.0371(3) Uani 1 1 d . . . . .
H5 H 0.229365 0.338020 0.018517 0.045 Uiso 1 1 calc R U . . .
C6 C 0.17178(18) 0.25777(10) 0.15215(13) 0.0367(3) Uani 1 1 d . . . . .
H6 H 0.081868 0.293935 0.172115 0.044 Uiso 1 1 calc R U . . .
C7 C 0.21378(16) 0.17950(9) 0.21444(11) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.152356 0.162374 0.276833 0.034 Uiso 1 1 calc R U . . .
C8 C 0.56931(15) 0.02423(9) 0.27964(11) 0.0248(3) Uani 1 1 d . . . . .
C10 C 0.80018(18) 0.05256(11) 0.40688(14) 0.0403(4) Uani 1 1 d . . . . .
H10 H 0.848005 0.076259 0.479168 0.048 Uiso 1 1 calc R U . . .
C11 C 0.90245(17) 0.01366(12) 0.33304(15) 0.0453(4) Uani 1 1 d . . . . .
H11 H 1.018700 0.012376 0.352784 0.054 Uiso 1 1 calc R U . . .
C12 C 0.83308(18) -0.02360(12) 0.22943(15) 0.0446(4) Uani 1 1 d . . . . .
H12 H 0.900723 -0.051988 0.177378 0.054 Uiso 1 1 calc R U . . .
C13 C 0.66334(17) -0.01890(11) 0.20269(12) 0.0348(3) Uani 1 1 d . . . . .
H13 H 0.612474 -0.044901 0.132639 0.042 Uiso 1 1 calc R U . . .
C14 C 0.30128(14) -0.04614(9) 0.19503(11) 0.0258(3) Uani 1 1 d . . . . .
C15 C 0.21700(15) -0.04336(9) 0.08455(11) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.208349 0.012662 0.043039 0.033 Uiso 1 1 calc R U . . .
C16 C 0.14490(17) -0.12161(10) 0.03366(13) 0.0350(3) Uani 1 1 d . . . . .
H16 H 0.087413 -0.118793 -0.042120 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1568(2) -0.20294(10) 0.09301(15) 0.0432(4) Uani 1 1 d . . . . .
H17 H 0.106980 -0.256344 0.058676 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2418(2) -0.20674(11) 0.20303(16) 0.0501(4) Uani 1 1 d . . . . .
H18 H 0.251679 -0.263120 0.243679 0.060 Uiso 1 1 calc R U . . .
C19 C 0.31246(19) -0.12890(10) 0.25409(14) 0.0399(4) Uani 1 1 d . . . . .
H19 H 0.369075 -0.132003 0.330133 0.048 Uiso 1 1 calc R U . . .
N1 N 0.63545(14) 0.05868(8) 0.38166(10) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.31587(11) 0.04394(7) 0.36602(8) 0.0320(2) Uani 1 1 d . . . . .
H1 H 0.392086 0.056894 0.418034 0.048 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
C2 C1 C8 110.09(10) . . ?
C14 C1 C2 112.53(10) . . ?
C14 C1 C8 110.56(10) . . ?
O1 C1 C2 109.23(10) . . ?
O1 C1 C8 107.89(9) . . ?
O1 C1 C14 106.37(10) . . ?
C3 C2 C1 122.50(11) . . ?
C7 C2 C1 118.99(11) . . ?
C7 C2 C3 118.48(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.57(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.15(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.23(13) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.69(13) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 120.88(13) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C13 C8 C1 123.32(12) . . ?
N1 C8 C1 114.22(11) . . ?
N1 C8 C13 122.45(12) . . ?
C11 C10 H10 118.5 . . ?
N1 C10 H10 118.5 . . ?
N1 C10 C11 123.07(14) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.74(13) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.95(15) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 C12 118.87(14) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C1 123.39(11) . . ?
C15 C14 C19 118.57(12) . . ?
C19 C14 C1 118.04(12) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.82(13) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.00(13) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.72(14) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.35(15) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.53(14) . . ?
C18 C19 H19 119.7 . . ?
C8 N1 C10 117.86(13) . . ?
C1 O1 H1 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
C1 C2 1.5342(17) . ?
C1 C8 1.5344(16) . ?
C1 C14 1.5292(17) . ?
C1 O1 1.4265(14) . ?
C2 C3 1.3947(18) . ?
C2 C7 1.3780(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3859(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3790(19) . ?
C7 H7 0.9500 . ?
C8 C13 1.3815(19) . ?
C8 N1 1.3426(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(2) . ?
C10 N1 1.3448(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3858(18) . ?
C14 C19 1.3904(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3915(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(2) . ?
C19 H19 0.9500 . ?
O1 H1 0.8400 . ?
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
C1 C2 C3 C4 177.40(12) . . . . ?
C1 C2 C7 C6 -177.77(12) . . . . ?
C1 C8 C13 C12 176.96(13) . . . . ?
C1 C8 N1 C10 -177.79(11) . . . . ?
C1 C14 C15 C16 -179.38(12) . . . . ?
C1 C14 C19 C18 179.91(14) . . . . ?
C2 C1 C8 C13 -87.16(15) . . . . ?
C2 C1 C8 N1 92.52(12) . . . . ?
C2 C1 C14 C15 5.85(16) . . . . ?
C2 C1 C14 C19 -173.58(12) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C2 C7 C6 0.32(19) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C7 C2 C3 C4 -0.62(19) . . . . ?
C8 C1 C2 C3 41.15(16) . . . . ?
C8 C1 C2 C7 -140.84(12) . . . . ?
C8 C1 C14 C15 -117.70(13) . . . . ?
C8 C1 C14 C19 62.87(15) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C10 N1 C8 0.5(2) . . . . ?
C11 C12 C13 C8 1.1(2) . . . . ?
C13 C8 N1 C10 1.9(2) . . . . ?
C14 C1 C2 C3 -82.66(14) . . . . ?
C14 C1 C2 C7 95.35(13) . . . . ?
C14 C1 C8 C13 37.79(16) . . . . ?
C14 C1 C8 N1 -142.54(11) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C14 C19 C18 0.5(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C14 -1.0(3) . . . . ?
C19 C14 C15 C16 0.05(19) . . . . ?
N1 C8 C13 C12 -2.7(2) . . . . ?
N1 C10 C11 C12 -2.1(2) . . . . ?
O1 C1 C2 C3 159.44(11) . . . . ?
O1 C1 C2 C7 -22.55(15) . . . . ?
O1 C1 C8 C13 153.72(12) . . . . ?
O1 C1 C8 N1 -26.60(14) . . . . ?
O1 C1 C14 C15 125.42(12) . . . . ?
O1 C1 C14 C19 -54.01(14) . . . . ?
