#------------------------------------------------------------------------------
#$Date: 2019-11-11 15:18:20 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/48/4034830.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_4034830
loop_
_publ_author_name
'Shangpliang, O. Risuklang'
'Kshiar, Baskhemlang'
'Wanniang, Kmendashisha'
'Marpna, Ibakyntiew D.'
'Lipon, Tyrchain Mitre'
'Laloo, Badaker M.'
'Myrboh, Bekington'
_publ_section_title
;
 Selenium Dioxide As an Alternative Reagent for the Direct
 α-Selenoamidation of Aryl Methyl Ketones.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5829
_journal_page_last               5835
_journal_paper_doi               10.1021/acs.joc.8b00558
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C11 H14 N2 O Se'
_chemical_formula_sum            'C11 H14 N2 O Se'
_chemical_formula_weight         269.20
_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     direct
_audit_creation_date             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.100(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1752(17)
_cell_length_b                   7.1057(6)
_cell_length_c                   13.7654(16)
_cell_measurement_reflns_used    833
_cell_measurement_temperature    296.5(2)
_cell_measurement_theta_max      24.2390
_cell_measurement_theta_min      4.1630
_cell_volume                     1202.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.5(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -4.00  72.00   1.00    1.76    --   19.93  37.00 120.00   76
  2  ω     41.00  67.00   1.00    1.76    --   19.93 178.00-120.00   26
  3  ω      0.00  92.00   1.00    1.76    --   19.93  37.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0215234000
_diffrn_orient_matrix_UB_12      0.0270695000
_diffrn_orient_matrix_UB_13      -0.0531272000
_diffrn_orient_matrix_UB_21      -0.0534578000
_diffrn_orient_matrix_UB_22      -0.0165269000
_diffrn_orient_matrix_UB_23      -0.0009225000
_diffrn_orient_matrix_UB_31      -0.0032104000
_diffrn_orient_matrix_UB_32      0.0946406000
_diffrn_orient_matrix_UB_33      0.0149784000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4128
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         3.405
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.688
_refine_diff_density_min         -1.582
_refine_diff_density_rms         0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0764
_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)+(0.1067P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1615
_reflns_number_total             2440
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00558_si_008.cif
_cod_data_source_block           r-329
_cod_database_code               4034830
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C11H14ON2Se
_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.
;
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2018-04-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.792
_oxdiff_exptl_absorpt_empirical_full_min 0.594
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
Se1 Se 0.73950(6) 0.07528(9) 0.45536(6) 0.0466(3) Uani 1 1 d .
O1 O 0.8299(4) 0.4890(8) 0.5865(3) 0.0482(12) Uani 1 1 d .
N2 N 0.8388(4) 0.3500(7) 0.3712(3) 0.0291(11) Uani 1 1 d .
C1 C 0.7877(4) 0.3069(8) 0.4335(4) 0.0282(13) Uani 1 1 d .
C2 C 0.7645(5) 0.4536(8) 0.4997(5) 0.0296(13) Uani 1 1 d .
N1 N 0.6019(4) 0.5287(9) 0.3562(4) 0.0444(14) Uani 1 1 d .
C3 C 0.6571(5) 0.5496(8) 0.4581(5) 0.0296(13) Uani 1 1 d .
C4 C 0.6209(6) 0.6579(9) 0.5224(6) 0.0455(17) Uani 1 1 d .
H4 H 0.662430 0.669558 0.592815 0.055 Uiso 1 1 calc R
C8 C 0.8629(5) 0.2086(10) 0.3039(5) 0.0431(16) Uani 1 1 d .
H8A H 0.859192 0.268101 0.239266 0.052 Uiso 1 1 calc R
H8B H 0.807976 0.110683 0.287045 0.052 Uiso 1 1 calc R
C10 C 0.8761(6) 0.5439(9) 0.3622(5) 0.0422(16) Uani 1 1 d .
H10A H 0.950160 0.539657 0.363395 0.051 Uiso 1 1 calc R
H10B H 0.876056 0.617619 0.421512 0.051 Uiso 1 1 calc R
C11 C 0.8034(7) 0.6386(11) 0.2623(6) 0.0520(19) Uani 1 1 d .
H11A H 0.805459 0.568313 0.203457 0.078 Uiso 1 1 calc GR
H11B H 0.828814 0.764323 0.259435 0.078 Uiso 1 1 calc GR
H11C H 0.730092 0.642769 0.260936 0.078 Uiso 1 1 calc GR
C5 C 0.5214(7) 0.7490(10) 0.4801(8) 0.061(2) Uani 1 1 d .
H5 H 0.493500 0.819225 0.521802 0.073 Uiso 1 1 calc R
C9 C 0.9722(7) 0.1217(13) 0.3541(7) 0.067(2) Uani 1 1 d .
H9A H 0.981885 0.023791 0.310181 0.100 Uiso 1 1 calc GR
H9B H 0.977978 0.069488 0.420196 0.100 Uiso 1 1 calc GR
H9C H 1.027358 0.215951 0.364343 0.100 Uiso 1 1 calc GR
C7 C 0.5087(6) 0.6242(13) 0.3166(6) 0.064(2) Uani 1 1 d .
H7 H 0.470838 0.617015 0.245207 0.077 Uiso 1 1 calc R
C6 C 0.4651(7) 0.7321(12) 0.3745(9) 0.073(3) Uani 1 1 d .
H6 H 0.398833 0.792917 0.343034 0.088 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'
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'
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 N2 C8 122.1(5)
C1 N2 C10 122.5(5)
C8 N2 C10 115.3(5)
N2 C1 Se1 127.7(4)
N2 C1 C2 120.5(5)
C2 C1 Se1 111.8(4)
O1 C2 C1 121.0(5)
O1 C2 C3 121.3(6)
C1 C2 C3 117.6(5)
C3 N1 C7 116.4(6)
N1 C3 C2 115.8(5)
N1 C3 C4 123.5(6)
C4 C3 C2 120.6(6)
C3 C4 H4 120.5
C3 C4 C5 118.9(7)
C5 C4 H4 120.5
N2 C8 H8A 109.1
N2 C8 H8B 109.1
N2 C8 C9 112.4(5)
H8A C8 H8B 107.9
C9 C8 H8A 109.1
C9 C8 H8B 109.1
N2 C10 H10A 109.3
N2 C10 H10B 109.3
N2 C10 C11 111.5(6)
H10A C10 H10B 108.0
C11 C10 H10A 109.3
C11 C10 H10B 109.3
C10 C11 H11A 109.5
C10 C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11B 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C4 C5 H5 121.0
C6 C5 C4 118.0(7)
C6 C5 H5 121.0
C8 C9 H9A 109.5
C8 C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C7 H7 117.9
N1 C7 C6 124.2(8)
C6 C7 H7 117.9
C5 C6 H6 120.6
C7 C6 C5 118.9(8)
C7 C6 H6 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C1 1.827(6)
O1 C2 1.222(7)
N2 C1 1.304(7)
N2 C8 1.476(8)
N2 C10 1.483(8)
C1 C2 1.486(8)
C2 C3 1.487(8)
N1 C3 1.336(8)
N1 C7 1.336(9)
C3 C4 1.381(9)
C4 H4 0.9300
C4 C5 1.388(10)
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.489(10)
C10 H10A 0.9700
C10 H10B 0.9700
C10 C11 1.521(10)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C5 H5 0.9300
C5 C6 1.379(13)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C7 H7 0.9300
C7 C6 1.371(12)
C6 H6 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
Se1 C1 C2 O1 89.8(6)
Se1 C1 C2 C3 -87.6(5)
O1 C2 C3 N1 167.1(6)
O1 C2 C3 C4 -10.8(9)
N2 C1 C2 O1 -88.8(7)
N2 C1 C2 C3 93.7(7)
C1 N2 C8 C9 -92.7(8)
C1 N2 C10 C11 -104.4(6)
C1 C2 C3 N1 -15.5(8)
C1 C2 C3 C4 166.6(5)
C2 C3 C4 C5 178.4(6)
N1 C3 C4 C5 0.7(10)
N1 C7 C6 C5 1.8(14)
C3 N1 C7 C6 -3.4(12)
C3 C4 C5 C6 -2.3(10)
C4 C5 C6 C7 1.2(12)
C8 N2 C1 Se1 1.9(8)
C8 N2 C1 C2 -179.7(5)
C8 N2 C10 C11 75.2(7)
C10 N2 C1 Se1 -178.5(4)
C10 N2 C1 C2 -0.1(8)
C10 N2 C8 C9 87.7(7)
C7 N1 C3 C2 -175.7(6)
C7 N1 C3 C4 2.1(10)
