#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:02:46 +0100 (Fri 04 de Feb de 2022) $
#$Revision: 272775 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/84/7158446.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_7158446
loop_
_publ_author_name
'Zhou, Chen-Fan'
'Zhang, Yun-Qian'
'Ling, Yong'
'Ming, Liang'
'Xi, Xia'
'Liu, Gong-Qing'
'Zhang, Yanan'
_publ_section_title
;
 Time-economical synthesis of selenofunctionalized heterocycles via
 I₂O₅-mediated selenylative heterocyclization.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              420
_journal_page_last               426
_journal_paper_doi               10.1039/d1ob02196f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C17 H14 Br N O3 Se'
_chemical_formula_sum            'C17 H14 Br N O3 Se'
_chemical_formula_weight         439.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-24
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-01 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.002(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5541(7)
_cell_length_b                   6.6650(4)
_cell_length_c                   20.2899(11)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.9230
_cell_measurement_theta_min      3.1460
_cell_volume                     1654.19(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   6.00   1.00    5.00    --  -11.27 -38.00  30.00   85
  2  ω    -14.00  25.00   1.00    5.00    --  -11.27 -99.00-120.00   39
  3  ω    -80.00   9.00   1.00    5.00    --  -11.27 -38.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068999000
_diffrn_orient_matrix_UB_12      -0.0394106000
_diffrn_orient_matrix_UB_13      -0.0312510000
_diffrn_orient_matrix_UB_21      -0.0571209000
_diffrn_orient_matrix_UB_22      0.0076475000
_diffrn_orient_matrix_UB_23      -0.0134098000
_diffrn_orient_matrix_UB_31      0.0071467000
_diffrn_orient_matrix_UB_32      0.0985789000
_diffrn_orient_matrix_UB_33      -0.0114393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0174P)²+1.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2327
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02196f2.cif
_cod_data_source_block           se
_cod_depositor_comments
'Adding full bibliography for 7158446--7158447.cif.'
_cod_database_code               7158446
_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.
;
_reflns_odcompleteness_completeness 99.92
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 1.915
_oxdiff_exptl_absorpt_empirical_full_min 0.687
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.06995(3) 0.15842(6) 0.43546(2) 0.04128(13) Uani 1 1 d . . . . .
Se1 Se 0.64044(3) 0.35181(5) 0.76239(2) 0.02818(12) Uani 1 1 d . . . . .
O1 O 0.43410(18) 0.7644(3) 0.65115(11) 0.0259(6) Uani 1 1 d . . . . .
O2 O 0.42986(17) 0.5229(3) 0.80388(11) 0.0203(5) Uani 1 1 d . . . . .
O3 O 0.30421(18) 0.2820(3) 0.77149(12) 0.0280(6) Uani 1 1 d . . . . .
N1 N 0.3578(2) 0.4904(4) 0.69333(13) 0.0156(6) Uani 1 1 d . . . . .
C1 C 0.6256(3) 0.3424(5) 0.66647(18) 0.0236(8) Uani 1 1 d . . . . .
C2 C 0.6436(3) 0.5023(5) 0.62680(19) 0.0295(9) Uani 1 1 d . . . . .
H2 H 0.660204 0.628459 0.645961 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6365(3) 0.4732(6) 0.5582(2) 0.0395(10) Uani 1 1 d . . . . .
H3 H 0.646442 0.581470 0.531348 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6151(3) 0.2867(6) 0.5295(2) 0.0429(11) Uani 1 1 d . . . . .
H4 H 0.611416 0.267919 0.483649 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5992(3) 0.1277(6) 0.5697(2) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.586010 0.000448 0.550838 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6026(3) 0.1548(5) 0.63740(19) 0.0307(9) Uani 1 1 d . . . . .
H6 H 0.589348 0.047180 0.663617 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6036(3) 0.6277(5) 0.78052(18) 0.0222(8) Uani 1 1 d . . . . .
H7A H 0.639283 0.659664 0.826861 0.027 Uiso 1 1 calc R U . . .
H7B H 0.634048 0.715688 0.751398 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4825(2) 0.6755(4) 0.77061(16) 0.0182(7) Uani 1 1 d . . . . .
C9 C 0.4666(3) 0.8779(5) 0.80058(19) 0.0294(9) Uani 1 1 d . . . . .
H9A H 0.389922 0.907276 0.792715 0.044 Uiso 1 1 calc R U . . .
H9B H 0.502287 0.979228 0.779684 0.044 Uiso 1 1 calc R U . . .
H9C H 0.497538 0.875829 0.848362 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4237(2) 0.6570(4) 0.69738(17) 0.0174(7) Uani 1 1 d . . . . .
C11 C 0.3581(3) 0.4159(5) 0.75779(17) 0.0191(7) Uani 1 1 d . . . . .
C12 C 0.2892(2) 0.4116(5) 0.63266(16) 0.0174(7) Uani 1 1 d . . . . .
C13 C 0.2994(3) 0.2122(5) 0.61630(18) 0.0260(8) Uani 1 1 d . . . . .
H13 H 0.350146 0.129909 0.644222 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2330(3) 0.1374(5) 0.55766(19) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.237738 0.003123 0.546200 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1601(3) 0.2616(5) 0.51656(17) 0.0262(8) Uani 1 1 d . . . . .
C16 C 0.1507(3) 0.4602(5) 0.53239(17) 0.0247(8) Uani 1 1 d . . . . .
H16 H 0.101452 0.542974 0.503595 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2152(3) 0.5362(5) 0.59163(17) 0.0211(8) Uani 1 1 d . . . . .
H17 H 0.208570 0.669589 0.603554 0.025 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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C7 104.46(14) . . ?
C11 O2 C8 110.5(2) . . ?
C10 N1 C11 110.8(3) . . ?
C10 N1 C12 125.7(3) . . ?
C11 N1 C12 123.2(3) . . ?
C2 C1 Se1 125.1(3) . . ?
C2 C1 C6 119.6(3) . . ?
C6 C1 Se1 115.2(3) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
Se1 C7 H7A 108.2 . . ?
Se1 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 Se1 116.4(2) . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
O2 C8 C7 109.7(2) . . ?
O2 C8 C9 108.8(3) . . ?
O2 C8 C10 103.1(2) . . ?
C9 C8 C7 110.6(3) . . ?
C10 C8 C7 111.5(3) . . ?
C10 C8 C9 112.9(3) . . ?
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 . . ?
O1 C10 N1 126.8(3) . . ?
O1 C10 C8 127.0(3) . . ?
N1 C10 C8 106.2(3) . . ?
O2 C11 N1 108.8(3) . . ?
O3 C11 O2 124.1(3) . . ?
O3 C11 N1 127.1(3) . . ?
C13 C12 N1 119.2(3) . . ?
C17 C12 N1 119.4(3) . . ?
C17 C12 C13 121.4(3) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Br1 119.6(3) . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 Br1 119.0(3) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 119.2(3) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
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
Br1 C15 1.904(3) . ?
Se1 C1 1.914(3) . ?
Se1 C7 1.951(3) . ?
O1 C10 1.210(4) . ?
O2 C8 1.458(4) . ?
O2 C11 1.347(4) . ?
O3 C11 1.190(4) . ?
N1 C10 1.377(4) . ?
N1 C11 1.398(4) . ?
N1 C12 1.434(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(4) . ?
C8 C9 1.512(4) . ?
C8 C10 1.508(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C13 1.383(4) . ?
C12 C17 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(5) . ?
C15 C16 1.374(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C15 C16 C17 179.3(2) . . . . ?
Se1 C1 C2 C3 176.1(3) . . . . ?
Se1 C1 C6 C5 -174.6(3) . . . . ?
Se1 C7 C8 O2 47.7(3) . . . . ?
Se1 C7 C8 C9 167.6(2) . . . . ?
Se1 C7 C8 C10 -65.9(3) . . . . ?
O2 C8 C10 O1 173.9(3) . . . . ?
O2 C8 C10 N1 -7.5(3) . . . . ?
N1 C12 C13 C14 -180.0(3) . . . . ?
N1 C12 C17 C16 178.7(3) . . . . ?
C1 C2 C3 C4 -1.9(6) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 -2.1(6) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C7 C8 C10 O1 -68.5(4) . . . . ?
C7 C8 C10 N1 110.1(3) . . . . ?
C8 O2 C11 O3 180.0(3) . . . . ?
C8 O2 C11 N1 -0.8(3) . . . . ?
C9 C8 C10 O1 56.8(4) . . . . ?
C9 C8 C10 N1 -124.7(3) . . . . ?
C10 N1 C11 O2 -4.5(3) . . . . ?
C10 N1 C11 O3 174.8(3) . . . . ?
C10 N1 C12 C13 126.1(3) . . . . ?
C10 N1 C12 C17 -53.3(4) . . . . ?
C11 O2 C8 C7 -113.7(3) . . . . ?
C11 O2 C8 C9 125.2(3) . . . . ?
C11 O2 C8 C10 5.1(3) . . . . ?
C11 N1 C10 O1 -173.9(3) . . . . ?
C11 N1 C10 C8 7.6(3) . . . . ?
C11 N1 C12 C13 -60.1(4) . . . . ?
C11 N1 C12 C17 120.5(3) . . . . ?
C12 N1 C10 O1 0.6(5) . . . . ?
C12 N1 C10 C8 -178.0(3) . . . . ?
C12 N1 C11 O2 -179.1(2) . . . . ?
C12 N1 C11 O3 0.1(5) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C12 C17 C16 -0.7(5) . . . . ?
C13 C14 C15 Br1 179.3(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C12 1.4(5) . . . . ?
C17 C12 C13 C14 -0.6(5) . . . . ?
