#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/24/1542441.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_1542441
loop_
_publ_author_name
'Tang, E.'
'Zhao, Yinjiao'
'Li, Wen'
'Wang, Weilin'
'Zhang, Meng'
'Dai, Xin'
_publ_section_title
;
 Catalytic Selenium-Promoted Intermolecular Friedel-Crafts Alkylation with
 Simple Alkenes.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              912
_journal_paper_doi               10.1021/acs.orglett.5b03579
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C21 H26 O3 Se'
_chemical_formula_weight         405.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4940(8)
_cell_length_b                   15.0837(17)
_cell_length_c                   17.3328(19)
_cell_measurement_reflns_used    3014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.10
_cell_measurement_theta_min      2.39
_cell_volume                     1924.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10788
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  0.6495
_exptl_absorpt_correction_T_min  0.5898
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2589
_reflns_number_total             3432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03579_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542441--1542442.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1542441
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2601(3) 1.06227(10) 0.33774(10) 0.0485(5) Uani 1 1 d .
O2 O 0.1834(3) 0.88904(12) 0.56503(10) 0.0555(5) Uani 1 1 d .
O3 O 0.0331(2) 0.77217(10) 0.30631(10) 0.0459(5) Uani 1 1 d .
Se1 Se 0.50823(4) 0.851289(19) 0.245621(18) 0.05356(13) Uani 1 1 d .
C1 C 0.2166(3) 0.98580(15) 0.37311(14) 0.0349(6) Uani 1 1 d .
C2 C 0.2313(3) 0.97961(16) 0.45464(14) 0.0404(6) Uani 1 1 d .
H2 H 0.2769 1.0267 0.4871 0.048 Uiso 1 1 calc R
C3 C 0.1770(3) 0.90242(16) 0.48587(14) 0.0407(6) Uani 1 1 d .
C4 C 0.1100(3) 0.83220(16) 0.43770(15) 0.0404(6) Uani 1 1 d .
H4 H 0.0717 0.7807 0.4591 0.049 Uiso 1 1 calc R
C5 C 0.1005(3) 0.83913(14) 0.35757(14) 0.0348(6) Uani 1 1 d .
C6 C 0.1563(3) 0.91554(14) 0.32248(13) 0.0320(5) Uani 1 1 d .
C7 C 0.1438(3) 0.92452(15) 0.23426(13) 0.0341(6) Uani 1 1 d .
H7 H 0.2011 0.9812 0.2259 0.041 Uiso 1 1 calc R
C8 C -0.0532(4) 0.93097(18) 0.19087(15) 0.0467(6) Uani 1 1 d .
H8A H -0.1167 0.8770 0.1996 0.056 Uiso 1 1 calc R
H8B H -0.1121 0.9799 0.2124 0.056 Uiso 1 1 calc R
C9 C -0.0684(5) 0.94491(19) 0.10309(15) 0.0621(8) Uani 1 1 d .
H9A H -0.1954 0.9448 0.0778 0.075 Uiso 1 1 calc R
H9B H -0.0173 1.0021 0.0937 0.075 Uiso 1 1 calc R
C10 C 0.0313(5) 0.87257(19) 0.06829(16) 0.0606(9) Uani 1 1 d .
H10A H 0.0247 0.8840 0.0128 0.073 Uiso 1 1 calc R
H10B H -0.0274 0.8161 0.0734 0.073 Uiso 1 1 calc R
C11 C 0.2285(4) 0.86717(18) 0.10865(16) 0.0542(8) Uani 1 1 d .
H11A H 0.2901 0.9216 0.0993 0.065 Uiso 1 1 calc R
H11B H 0.2868 0.8186 0.0864 0.065 Uiso 1 1 calc R
C12 C 0.2466(3) 0.85306(15) 0.19678(14) 0.0377(6) Uani 1 1 d .
H12 H 0.1943 0.7952 0.2053 0.045 Uiso 1 1 calc R
C13 C 0.2394(4) 0.9618(2) 0.61661(15) 0.0591(8) Uani 1 1 d .
H13A H 0.3638 0.9761 0.6156 0.089 Uiso 1 1 calc R
H13B H 0.2280 0.9459 0.6691 0.089 Uiso 1 1 calc R
H13C H 0.1641 1.0123 0.5998 0.089 Uiso 1 1 calc R
C14 C 0.2864(5) 1.14134(16) 0.38359(18) 0.0640(9) Uani 1 1 d .
H14A H 0.1826 1.1512 0.4076 0.096 Uiso 1 1 calc R
H14B H 0.3010 1.1907 0.3504 0.096 Uiso 1 1 calc R
H14C H 0.3931 1.1354 0.4237 0.096 Uiso 1 1 calc R
C15 C -0.0005(4) 0.68810(16) 0.33729(16) 0.0506(7) Uani 1 1 d .
H15A H 0.1085 0.6668 0.3704 0.076 Uiso 1 1 calc R
H15B H -0.0377 0.6471 0.2950 0.076 Uiso 1 1 calc R
H15C H -0.0949 0.6934 0.3675 0.076 Uiso 1 1 calc R
C16 C 0.5109(3) 0.75614(16) 0.31935(16) 0.0437(6) Uani 1 1 d .
C17 C 0.5485(4) 0.77135(19) 0.39969(17) 0.0576(8) Uani 1 1 d .
H17 H 0.5690 0.8288 0.4187 0.069 Uiso 1 1 calc R
C18 C 0.5557(5) 0.7021(2) 0.45117(19) 0.0714(9) Uani 1 1 d .
H18 H 0.5820 0.7128 0.5050 0.086 Uiso 1 1 calc R
C19 C 0.5246(5) 0.6171(2) 0.4242(2) 0.0710(9) Uani 1 1 d .
H19 H 0.5297 0.5704 0.4596 0.085 Uiso 1 1 calc R
C20 C 0.4858(4) 0.60098(19) 0.3447(2) 0.0654(9) Uani 1 1 d .
H20 H 0.4631 0.5434 0.3262 0.079 Uiso 1 1 calc R
C21 C 0.4805(4) 0.67004(18) 0.29242(18) 0.0523(7) Uani 1 1 d .
H21 H 0.4564 0.6588 0.2387 0.063 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C1 O1 C14 118.21(19)
C3 O2 C13 117.5(2)
C5 O3 C15 118.78(18)
C16 Se1 C12 100.34(10)
O1 C1 C6 115.6(2)
O1 C1 C2 121.8(2)
C6 C1 C2 122.6(2)
C3 C2 C1 118.7(2)
C3 C2 H2 120.6
C1 C2 H2 120.6
O2 C3 C2 123.9(2)
O2 C3 C4 115.4(2)
C2 C3 C4 120.7(2)
C5 C4 C3 119.5(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
O3 C5 C4 122.4(2)
O3 C5 C6 115.2(2)
C4 C5 C6 122.3(2)
C1 C6 C5 116.0(2)
C1 C6 C7 121.1(2)
C5 C6 C7 122.8(2)
C6 C7 C8 111.76(19)
C6 C7 C12 114.96(19)
C8 C7 C12 110.5(2)
C6 C7 H7 106.3
C8 C7 H7 106.3
C12 C7 H7 106.3
C9 C8 C7 112.6(2)
C9 C8 H8A 109.1
C7 C8 H8A 109.1
C9 C8 H8B 109.1
C7 C8 H8B 109.1
H8A C8 H8B 107.8
C10 C9 C8 110.5(2)
C10 C9 H9A 109.5
C8 C9 H9A 109.5
C10 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
C9 C10 C11 111.6(2)
C9 C10 H10A 109.3
C11 C10 H10A 109.3
C9 C10 H10B 109.3
C11 C10 H10B 109.3
H10A C10 H10B 108.0
C10 C11 C12 111.4(2)
C10 C11 H11A 109.3
C12 C11 H11A 109.3
C10 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 108.0
C11 C12 C7 111.7(2)
C11 C12 Se1 108.87(17)
C7 C12 Se1 111.25(16)
C11 C12 H12 108.3
C7 C12 H12 108.3
Se1 C12 H12 108.3
O2 C13 H13A 109.5
O2 C13 H13B 109.5
H13A C13 H13B 109.5
O2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C21 C16 C17 118.9(3)
C21 C16 Se1 119.8(2)
C17 C16 Se1 121.3(2)
C18 C17 C16 120.3(3)
C18 C17 H17 119.9
C16 C17 H17 119.9
C19 C18 C17 120.6(3)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 119.8(3)
C18 C19 H19 120.1
C20 C19 H19 120.1
C19 C20 C21 120.0(3)
C19 C20 H20 120.0
C21 C20 H20 120.0
C20 C21 C16 120.4(3)
C20 C21 H21 119.8
C16 C21 H21 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.374(3)
O1 C14 1.426(3)
O2 C3 1.379(3)
O2 C13 1.428(3)
O3 C5 1.377(3)
O3 C15 1.418(3)
Se1 C16 1.919(3)
Se1 C12 1.984(3)
C1 C6 1.396(3)
C1 C2 1.400(3)
C2 C3 1.378(3)
C2 H2 0.9300
C3 C4 1.383(3)
C4 C5 1.381(3)
C4 H4 0.9300
C5 C6 1.403(3)
C6 C7 1.520(3)
C7 C8 1.528(3)
C7 C12 1.538(3)
C7 H7 0.9800
C8 C9 1.519(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.511(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.513(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.523(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 H12 0.9800
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C21 1.384(4)
C16 C17 1.387(4)
C17 C18 1.368(4)
C17 H17 0.9300
C18 C19 1.369(4)
C18 H18 0.9300
C19 C20 1.375(5)
C19 H19 0.9300
C20 C21 1.376(4)
C20 H20 0.9300
C21 H21 0.9300
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
C14 O1 C1 C6 167.4(2)
C14 O1 C1 C2 -12.3(3)
O1 C1 C2 C3 176.8(2)
C6 C1 C2 C3 -2.8(4)
C13 O2 C3 C2 4.0(4)
C13 O2 C3 C4 -175.7(2)
C1 C2 C3 O2 -179.3(2)
C1 C2 C3 C4 0.3(4)
O2 C3 C4 C5 -179.2(2)
C2 C3 C4 C5 1.1(4)
C15 O3 C5 C4 -10.4(3)
C15 O3 C5 C6 170.6(2)
C3 C4 C5 O3 -179.1(2)
C3 C4 C5 C6 -0.2(4)
O1 C1 C6 C5 -176.1(2)
C2 C1 C6 C5 3.6(3)
O1 C1 C6 C7 0.9(3)
C2 C1 C6 C7 -179.4(2)
O3 C5 C6 C1 177.0(2)
C4 C5 C6 C1 -2.1(4)
O3 C5 C6 C7 0.0(3)
C4 C5 C6 C7 -179.0(2)
C1 C6 C7 C8 -107.4(3)
C5 C6 C7 C8 69.4(3)
C1 C6 C7 C12 125.5(2)
C5 C6 C7 C12 -57.7(3)
C6 C7 C8 C9 176.9(2)
C12 C7 C8 C9 -53.7(3)
C7 C8 C9 C10 55.6(3)
C8 C9 C10 C11 -56.4(3)
C9 C10 C11 C12 56.6(3)
C10 C11 C12 C7 -54.7(3)
C10 C11 C12 Se1 -177.89(17)
C6 C7 C12 C11 -179.6(2)
C8 C7 C12 C11 52.8(3)
C6 C7 C12 Se1 -57.7(2)
C8 C7 C12 Se1 174.62(16)
C16 Se1 C12 C11 -138.97(17)
C16 Se1 C12 C7 97.57(16)
C12 Se1 C16 C21 68.9(2)
C12 Se1 C16 C17 -113.1(2)
C21 C16 C17 C18 0.1(4)
Se1 C16 C17 C18 -177.8(2)
C16 C17 C18 C19 -0.5(5)
C17 C18 C19 C20 0.0(5)
C18 C19 C20 C21 0.8(5)
C19 C20 C21 C16 -1.2(5)
C17 C16 C21 C20 0.7(4)
Se1 C16 C21 C20 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048037
