#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:41:23 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127139.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_7127139
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         'C25 H18 N2 O'
_chemical_formula_sum            'C25 H18 N2 O'
_chemical_formula_weight         362.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.094(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8482(10)
_cell_length_b                   18.0365(10)
_cell_length_c                   12.5808(7)
_cell_measurement_reflns_used    4510
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      31.8433
_cell_measurement_theta_min      2.5636
_cell_volume                     3605.6(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         2.564
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0631 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.9420.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0477
_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)+(0.0660P)²+1.2047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4095
_reflns_number_total             5253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05164k2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7127135--7127141.cif.'
_cod_database_code               7127139
_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   0.977
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.20154(7) -0.03226(6) 0.50010(9) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.16780(7) 0.04172(6) 0.43368(10) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.15438(6) 0.16687(6) 0.45962(9) 0.0161(2) Uani 1 1 d . . . . .
C4 C 0.16556(7) 0.22745(6) 0.54050(10) 0.0178(2) Uani 1 1 d . . . . .
C5 C 0.20716(8) 0.26837(7) 0.73105(11) 0.0270(3) Uani 1 1 d . . . . .
H5 H 0.229204 0.258158 0.813943 0.032 Uiso 1 1 calc R U . . .
C6 C 0.18806(8) 0.34208(7) 0.69451(12) 0.0276(3) Uani 1 1 d . . . . .
H6 H 0.197061 0.380298 0.751025 0.033 Uiso 1 1 calc R U . . .
C7 C 0.15610(8) 0.35795(7) 0.57547(12) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.142349 0.407538 0.547995 0.030 Uiso 1 1 calc R U . . .
C8 C 0.14376(7) 0.29989(7) 0.49391(11) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.11123(8) 0.31191(7) 0.36834(11) 0.0237(3) Uani 1 1 d . . . . .
H9 H 0.096978 0.360788 0.337517 0.028 Uiso 1 1 calc R U . . .
C10 C 0.10037(8) 0.25508(7) 0.29263(11) 0.0228(3) Uani 1 1 d . . . . .
H10 H 0.078800 0.264609 0.209606 0.027 Uiso 1 1 calc R U . . .
C11 C 0.12096(7) 0.18078(6) 0.33597(10) 0.0184(2) Uani 1 1 d . . . . .
C12 C 0.11013(7) 0.11939(7) 0.26092(10) 0.0215(2) Uani 1 1 d . . . . .
H12 H 0.087072 0.126271 0.177056 0.026 Uiso 1 1 calc R U . . .
C13 C 0.13278(7) 0.04990(7) 0.30867(10) 0.0206(2) Uani 1 1 d . . . . .
H13 H 0.125096 0.008123 0.258750 0.025 Uiso 1 1 calc R U . . .
C14 C 0.28006(7) -0.05299(6) 0.48609(10) 0.0185(2) Uani 1 1 d . . . . .
C15 C 0.27305(7) -0.08205(7) 0.37935(10) 0.0218(2) Uani 1 1 d . . . . .
H15 H 0.218865 -0.091388 0.315374 0.026 Uiso 1 1 calc R U . . .
C16 C 0.34409(8) -0.09752(7) 0.36523(13) 0.0287(3) Uani 1 1 d . . . . .
H16 H 0.338330 -0.116894 0.291667 0.034 Uiso 1 1 calc R U . . .
C17 C 0.42350(9) -0.08476(8) 0.45833(14) 0.0343(3) Uani 1 1 d . . . . .
H17 H 0.472226 -0.094955 0.448560 0.041 Uiso 1 1 calc R U . . .
C18 C 0.43140(8) -0.05724(8) 0.56493(13) 0.0334(3) Uani 1 1 d . . . . .
H18 H 0.485822 -0.049213 0.629164 0.040 Uiso 1 1 calc R U . . .
C19 C 0.36037(8) -0.04106(7) 0.57954(11) 0.0253(3) Uani 1 1 d . . . . .
H19 H 0.366588 -0.021813 0.653414 0.030 Uiso 1 1 calc R U . . .
C20 C 0.13477(7) -0.09321(6) 0.45776(10) 0.0182(2) Uani 1 1 d . . . . .
C21 C 0.15755(8) -0.16752(7) 0.46513(11) 0.0229(3) Uani 1 1 d . . . . .
H21 H 0.214503 -0.180269 0.487987 0.027 Uiso 1 1 calc R U . . .
C22 C 0.09805(9) -0.22341(7) 0.43948(12) 0.0293(3) Uani 1 1 d . . . . .
H22 H 0.114491 -0.273926 0.445091 0.035 Uiso 1 1 calc R U . . .
C23 C 0.01473(8) -0.20532(8) 0.40571(12) 0.0299(3) Uani 1 1 d . . . . .
H23 H -0.026082 -0.243362 0.387778 0.036 Uiso 1 1 calc R U . . .
C24 C -0.00868(8) -0.13171(8) 0.39825(12) 0.0293(3) Uani 1 1 d . . . . .
H24 H -0.065694 -0.119176 0.375354 0.035 Uiso 1 1 calc R U . . .
C25 C 0.05076(8) -0.07603(7) 0.42408(11) 0.0247(3) Uani 1 1 d . . . . .
H25 H 0.034031 -0.025613 0.418757 0.030 Uiso 1 1 calc R U . . .
N1 N 0.17742(6) 0.09798(5) 0.50577(8) 0.0172(2) Uani 1 1 d . . . . .
N2 N 0.19682(6) 0.21170(6) 0.65877(9) 0.0215(2) Uani 1 1 d . . . . .
O1 O 0.22433(6) -0.02036(5) 0.62292(7) 0.0229(2) Uani 1 1 d . . . . .
H1 H 0.2201(9) 0.0294(9) 0.6265(13) 0.027 Uiso 1 1 d . 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
C14 C1 C2 107.44(9) . . ?
C20 C1 C2 112.53(9) . . ?
C20 C1 C14 113.10(9) . . ?
O1 C1 C2 107.78(9) . . ?
O1 C1 C14 109.67(9) . . ?
O1 C1 C20 106.19(8) . . ?
C13 C2 C1 124.01(10) . . ?
N1 C2 C1 113.34(9) . . ?
N1 C2 C13 122.61(10) . . ?
C11 C3 C4 119.71(10) . . ?
N1 C3 C4 118.35(9) . . ?
N1 C3 C11 121.93(10) . . ?
C8 C4 C3 118.96(10) . . ?
N2 C4 C3 117.99(10) . . ?
N2 C4 C8 123.06(10) . . ?
C6 C5 H5 117.6 . . ?
N2 C5 H5 117.6 . . ?
N2 C5 C6 124.88(12) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.48(11) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.33(12) . . ?
C8 C7 H7 120.3 . . ?
C4 C8 C9 119.69(11) . . ?
C7 C8 C4 117.54(11) . . ?
C7 C8 C9 122.77(11) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.29(11) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.82(11) . . ?
C11 C10 H10 119.6 . . ?
C3 C11 C10 119.52(10) . . ?
C12 C11 C3 117.29(10) . . ?
C12 C11 C10 123.19(10) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.14(10) . . ?
C13 C12 H12 119.9 . . ?
C2 C13 H13 120.7 . . ?
C12 C13 C2 118.50(11) . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C1 121.07(10) . . ?
C15 C14 C19 118.48(11) . . ?
C19 C14 C1 120.42(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.89(12) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.07(13) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.67(12) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.61(12) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.26(12) . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C1 120.80(10) . . ?
C21 C20 C25 118.38(11) . . ?
C25 C20 C1 120.40(10) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.89(11) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 119.96(12) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.71(12) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.26(12) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.79(12) . . ?
C24 C25 H25 119.6 . . ?
C2 N1 C3 119.49(9) . . ?
C5 N2 C4 116.72(11) . . ?
C1 O1 H1 102.4(9) . . ?
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 1.5438(15) . ?
C1 C14 1.5362(16) . ?
C1 C20 1.5278(16) . ?
C1 O1 1.4236(13) . ?
C2 C13 1.4108(15) . ?
C2 N1 1.3190(14) . ?
C3 C4 1.4435(15) . ?
C3 C11 1.4118(15) . ?
C3 N1 1.3538(14) . ?
C4 C8 1.4123(16) . ?
C4 N2 1.3600(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.3971(19) . ?
C5 N2 1.3240(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3682(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.4113(17) . ?
C8 C9 1.4297(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3518(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.4303(16) . ?
C11 C12 1.4102(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3689(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3931(16) . ?
C14 C19 1.3957(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3864(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3924(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3914(17) . ?
C20 C25 1.3947(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.3914(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3866(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.3876(18) . ?
C25 H25 0.9500 . ?
O1 H1 0.904(16) . ?
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 C13 C12 -175.73(10) . . . . ?
C1 C2 N1 C3 176.71(9) . . . . ?
C1 C14 C15 C16 177.03(11) . . . . ?
C1 C14 C19 C18 -177.51(11) . . . . ?
C1 C20 C21 C22 172.64(11) . . . . ?
C1 C20 C25 C24 -172.79(11) . . . . ?
C2 C1 C14 C15 -76.35(13) . . . . ?
C2 C1 C14 C19 101.83(12) . . . . ?
C2 C1 C20 C21 152.32(10) . . . . ?
C2 C1 C20 C25 -35.23(14) . . . . ?
C3 C4 C8 C7 -179.50(10) . . . . ?
C3 C4 C8 C9 -0.02(16) . . . . ?
C3 C4 N2 C5 179.40(10) . . . . ?
C3 C11 C12 C13 -0.90(16) . . . . ?
C4 C3 C11 C10 1.43(15) . . . . ?
C4 C3 C11 C12 -179.00(10) . . . . ?
C4 C3 N1 C2 179.98(10) . . . . ?
C4 C8 C9 C10 0.37(17) . . . . ?
C5 C6 C7 C8 -0.21(18) . . . . ?
C6 C5 N2 C4 0.29(19) . . . . ?
C6 C7 C8 C4 -0.09(16) . . . . ?
C6 C7 C8 C9 -179.55(11) . . . . ?
C7 C8 C9 C10 179.82(11) . . . . ?
C8 C4 N2 C5 -0.62(16) . . . . ?
C8 C9 C10 C11 0.18(18) . . . . ?
C9 C10 C11 C3 -1.09(17) . . . . ?
C9 C10 C11 C12 179.37(11) . . . . ?
C10 C11 C12 C13 178.65(11) . . . . ?
C11 C3 C4 C8 -0.88(15) . . . . ?
C11 C3 C4 N2 179.09(10) . . . . ?
C11 C3 N1 C2 -0.71(16) . . . . ?
C11 C12 C13 C2 -0.77(17) . . . . ?
C13 C2 N1 C3 -1.11(16) . . . . ?
C14 C1 C2 C13 67.24(13) . . . . ?
C14 C1 C2 N1 -110.55(10) . . . . ?
C14 C1 C20 C21 30.34(14) . . . . ?
C14 C1 C20 C25 -157.21(10) . . . . ?
C14 C15 C16 C17 0.58(19) . . . . ?
C15 C14 C19 C18 0.71(18) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 C19 -1.0(2) . . . . ?
C17 C18 C19 C14 0.4(2) . . . . ?
C19 C14 C15 C16 -1.18(18) . . . . ?
C20 C1 C2 C13 -57.90(14) . . . . ?
C20 C1 C2 N1 124.31(10) . . . . ?
C20 C1 C14 C15 48.45(14) . . . . ?
C20 C1 C14 C19 -133.37(11) . . . . ?
C20 C21 C22 C23 0.19(19) . . . . ?
C21 C20 C25 C24 -0.17(18) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 0.2(2) . . . . ?
C23 C24 C25 C20 0.06(19) . . . . ?
C25 C20 C21 C22 0.04(18) . . . . ?
N1 C2 C13 C12 1.86(17) . . . . ?
N1 C3 C4 C8 178.44(10) . . . . ?
N1 C3 C4 N2 -1.58(15) . . . . ?
N1 C3 C11 C10 -177.87(10) . . . . ?
N1 C3 C11 C12 1.70(16) . . . . ?
N2 C4 C8 C7 0.53(16) . . . . ?
N2 C4 C8 C9 -179.99(10) . . . . ?
N2 C5 C6 C7 0.1(2) . . . . ?
O1 C1 C2 C13 -174.64(10) . . . . ?
O1 C1 C2 N1 7.57(13) . . . . ?
O1 C1 C14 C15 166.77(10) . . . . ?
O1 C1 C14 C19 -15.06(15) . . . . ?
O1 C1 C20 C21 -89.99(12) . . . . ?
O1 C1 C20 C25 82.46(12) . . . . ?
