data_exp_754_dmdbs
_audit_creation_date              2019-02-02
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         4,6-dimethyldibenzoselenophene
_chemical_formula_moiety          'C14 H12 Se'
_chemical_formula_sum             'C14 H12 Se'
_chemical_formula_weight          259.20
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C56 H48 Se4 '
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 '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'
 'Se' 'Se' -0.7943 1.1372
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
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'

_cell_length_a                    9.74881(17)
_cell_length_b                    6.68747(14)
_cell_length_c                    16.9645(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90.7550(15)
_cell_angle_gamma                 90
_cell_volume                      1105.90(3)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     7224
_cell_measurement_temperature     297.60(10)
_cell_measurement_theta_max       77.4060
_cell_measurement_theta_min       5.2030
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     4.256
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.48407
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.5a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    .
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.557
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              520
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 1 -4 0 0.0679
 -1 -3 8 0.0976
 -2 3 8 0.0838
 -2 4 4 0.0855
 2 0 -10 0.0700
 6 0 -1 0.0226
 -6 0 1 0.0095

_exptl_crystal_preparation        ?
_exptl_crystal_recrystallization_method sublimation
_exptl_crystal_size_max           0.266
_exptl_crystal_size_mid           0.189
_exptl_crystal_size_min           0.037
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0.7773 -4.3112 0.0614 -0.1318 -0.5505 0.8244
 -1.2297 -2.9386 7.8514 0.0599 0.2486 0.9667
 -2.2535 2.6473 7.8459 0.2321 0.9678 -0.0975
 -1.6760 3.8328 4.3170 0.2010 0.8386 -0.5063
 2.3284 -0.0576 -10.2873 -0.1991 -0.8292 -0.5223
 6.3040 0.1645 -0.9169 0.7815 -0.5994 -0.1733
 -6.2865 -0.2829 1.1038 -0.7766 0.5957 0.2050

_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0249
_diffrn_reflns_av_unetI/netI      0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_number             10191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full         66.572
_diffrn_reflns_theta_max          66.572
_diffrn_reflns_theta_min          4.536
_diffrn_ambient_environment       air
_diffrn_ambient_temperature       297.60(10)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_detector_type             HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -21.00  59.00   0.50    1.00    --   50.24 -43.00 -11.00  160
  2  ω     34.00  60.00   0.50    3.22    --  105.75 -77.00  90.00   52
  3  ω     34.00 123.00   0.50    3.22    --  105.75 -77.00  90.00  178
  4  ω     93.00 123.00   0.50    3.22    --  105.75 -77.00  90.00   60
  5  ω     42.00  68.00   0.50    3.22    --  105.75 -37.00 150.00   52
  6  ω     32.00  72.00   0.50    3.22    --  105.75 -19.00 150.00   80
  7  ω     97.00 178.00   0.50    3.22    --  105.75  43.00 140.00  162
  8  ω     71.00 121.00   0.50    1.00    --   50.24 125.00 -30.00  100
  9  ω     71.00 121.00   0.50    1.00    --   50.24 125.00-150.00  100
 10  ω     37.00  75.00   0.50    3.22    --  105.75 -19.00 -60.00   76
 11  ω     50.00  75.00   0.50    3.22    --  105.75 -19.00-120.00   50
 12  ω     36.00  66.00   0.50    3.22    --  105.75 -37.00-150.00   60
 13  ω     38.00  66.00   0.50    3.22    --  105.75 -37.00-180.00   56
 14  ω     33.00  58.00   0.50    3.22    --  105.75 -37.00-120.00   50
 15  ω     34.00  75.00   0.50    3.22    --  105.75 -43.00 -11.00   82
 16  ω     35.00  61.00   0.50    3.22    --  105.75 -37.00   0.00   52
 17  ω    -59.00  22.00   0.50    1.00    --  -50.24  43.00 140.00  162
 18  ω    -58.00  22.00   0.50    1.00    --  -50.24  37.00-120.00  160
 19  ω    -69.00 -33.00   0.50    3.22    -- -105.75  37.00  60.00   72
 20  ω    -75.00 -34.00   0.50    3.22    -- -105.75  43.00 140.00   82
 21  ω    -76.00 -32.00   0.50    3.22    -- -105.75  19.00 120.00   88
 22  ω    -76.00 -32.00   0.50    3.22    -- -105.75  19.00 150.00   88
 23  ω    -69.00 -33.00   0.50    3.22    -- -105.75  37.00  90.00   72
 24  ω   -106.00 -34.00   0.50    3.22    -- -105.75  57.00   0.00  144
 25  ω   -121.00 -41.00   0.50    1.00    --  -50.24 -43.00 -11.00  160
 26  ω   -121.00 -70.00   0.50    1.00    --  -50.24-125.00 -30.00  102
 27  ω   -177.00 -97.00   0.50    3.22    -- -105.75 -43.00 -11.00  160
 28  ω   -177.00 -93.00   0.50    3.22    -- -105.75 -57.00 -30.00  168
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       0.1295754000
_diffrn_orient_matrix_UB_12       0.0546286000
_diffrn_orient_matrix_UB_13       0.0483722000
_diffrn_orient_matrix_UB_21       -0.0893220000
_diffrn_orient_matrix_UB_22       0.1124328000
_diffrn_orient_matrix_UB_23       0.0597570000
_diffrn_orient_matrix_UB_31       -0.0154127000
_diffrn_orient_matrix_UB_32       -0.1933049000
_diffrn_orient_matrix_UB_33       0.0483668000
_diffrn_oxdiff_ac3_digest_frames
;
01ffc993723964e5d5ab97d6126ed5b6e9028283eb8
;
_diffrn_oxdiff_ac3_digest_hkl
;
01298d075568fa750ca9461a4dae4629273349
;
_diffrn_radiation_monochromator   mirror
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54184
_diffrn_source                    'micro-focus sealed X-ray tube'
_diffrn_source_type               'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1829
_reflns_number_total              1953
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_collection        'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_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     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.594
_refine_diff_density_min          -0.482
_refine_diff_density_rms          0.083
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.222
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      138
_refine_ls_number_reflns          1953
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0328
_refine_ls_R_factor_gt            0.0299
_refine_ls_restrained_S_all       1.222
_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)+(0.0631P)²+0.5424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0873
_refine_ls_wR_factor_ref          0.1114
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C9(H9), C10(H10), C2(H2), C8(H8)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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
 Se1 Se 0.46370(3) 0.23478(5) 0.42286(2) 0.04798(18) Uani 1 1 d . . . . .
 C12 C 0.5731(3) 0.5830(4) 0.36401(14) 0.0424(6) Uani 1 1 d . . . . .
 C1 C 0.6717(4) 0.7267(5) 0.3475(2) 0.0522(8) Uani 1 1 d . . . . .
 H1 H 0.648980 0.838277 0.317323 0.063 Uiso 1 1 calc R . . . .
 C6 C 0.3555(3) 0.4164(4) 0.36261(15) 0.0440(6) Uani 1 1 d . . . . .
 C5 C 0.6110(3) 0.4156(4) 0.40925(14) 0.0420(6) Uani 1 1 d . . . . .
 C11 C 0.4301(3) 0.5822(4) 0.33831(14) 0.0425(6) Uani 1 1 d . . . . .
 C4 C 0.7435(3) 0.3895(4) 0.43939(15) 0.0459(6) Uani 1 1 d . . . . .
 C3 C 0.8383(3) 0.5352(5) 0.42193(17) 0.0537(7) Uani 1 1 d . . . . .
 H3 H 0.927597 0.521844 0.441103 0.064 Uiso 1 1 calc R . . . .
 C9 C 0.2276(4) 0.7022(5) 0.27181(19) 0.0568(8) Uani 1 1 d . . . . .
 H9 H 0.183561 0.797565 0.240601 0.068 Uiso 1 1 calc R . . . .
 C10 C 0.3643(4) 0.7266(5) 0.2918(2) 0.0522(8) Uani 1 1 d . . . . .
 H10 H 0.412194 0.838097 0.274389 0.063 Uiso 1 1 calc R . . . .
 C2 C 0.8045(4) 0.7017(5) 0.3765(2) 0.0576(8) Uani 1 1 d . . . . .
 H2 H 0.871210 0.796803 0.365584 0.069 Uiso 1 1 calc R . . . .
 C8 C 0.1550(3) 0.5362(5) 0.29801(17) 0.0568(8) Uani 1 1 d . . . . .
 H8 H 0.062601 0.524126 0.284586 0.068 Uiso 1 1 calc R . . . .
 C7 C 0.2166(3) 0.3887(5) 0.34349(16) 0.0490(7) Uani 1 1 d . . . . .
 C13 C 0.7800(4) 0.2098(5) 0.4890(2) 0.0586(9) Uani 1 1 d . . . . .
 H13A H 0.724084 0.207901 0.535150 0.088 Uiso 1 1 calc GR . . . .
 H13B H 0.874972 0.216934 0.504518 0.088 Uiso 1 1 calc GR . . . .
 H13C H 0.764329 0.090124 0.458975 0.088 Uiso 1 1 calc GR . . . .
 C14 C 0.1402(4) 0.2071(6) 0.3712(3) 0.0631(9) Uani 1 1 d . . . . .
 H14A H 0.145519 0.199553 0.427646 0.095 Uiso 1 1 calc GR . . . .
 H14B H 0.180312 0.089239 0.348861 0.095 Uiso 1 1 calc GR . . . .
 H14C H 0.045785 0.216505 0.354707 0.095 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 Se1 C6 1.898(3) . ?
 Se1 C5 1.894(3) . ?
 C12 C1 1.390(4) . ?
 C12 C5 1.404(4) . ?
 C12 C11 1.455(4) . ?
 C1 H1 0.9300 . ?
 C1 C2 1.390(5) . ?
 C6 C11 1.392(4) . ?
 C6 C7 1.400(4) . ?
 C5 C4 1.394(4) . ?
 C11 C10 1.398(4) . ?
 C4 C3 1.378(4) . ?
 C4 C13 1.507(4) . ?
 C3 H3 0.9300 . ?
 C3 C2 1.391(5) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.380(5) . ?
 C9 C8 1.392(5) . ?
 C10 H10 0.9300 . ?
 C2 H2 0.9300 . ?
 C8 H8 0.9300 . ?
 C8 C7 1.385(4) . ?
 C7 C14 1.504(5) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?

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
 C5 Se1 C6 86.72(12) . . ?
 C1 C12 C5 118.9(3) . . ?
 C1 C12 C11 127.2(3) . . ?
 C5 C12 C11 113.9(2) . . ?
 C12 C1 H1 120.4 . . ?
 C2 C1 C12 119.3(3) . . ?
 C2 C1 H1 120.4 . . ?
 C11 C6 Se1 112.38(19) . . ?
 C11 C6 C7 123.0(3) . . ?
 C7 C6 Se1 124.7(2) . . ?
 C12 C5 Se1 112.39(19) . . ?
 C4 C5 Se1 125.1(2) . . ?
 C4 C5 C12 122.5(3) . . ?
 C6 C11 C12 114.6(2) . . ?
 C6 C11 C10 118.7(3) . . ?
 C10 C11 C12 126.7(3) . . ?
 C5 C4 C13 121.1(3) . . ?
 C3 C4 C5 116.9(3) . . ?
 C3 C4 C13 122.0(3) . . ?
 C4 C3 H3 119.0 . . ?
 C4 C3 C2 122.1(3) . . ?
 C2 C3 H3 119.0 . . ?
 C10 C9 H9 119.7 . . ?
 C10 C9 C8 120.6(3) . . ?
 C8 C9 H9 119.7 . . ?
 C11 C10 H10 120.3 . . ?
 C9 C10 C11 119.5(3) . . ?
 C9 C10 H10 120.3 . . ?
 C1 C2 C3 120.3(3) . . ?
 C1 C2 H2 119.8 . . ?
 C3 C2 H2 119.8 . . ?
 C9 C8 H8 119.1 . . ?
 C7 C8 C9 121.8(3) . . ?
 C7 C8 H8 119.1 . . ?
 C6 C7 C14 121.1(3) . . ?
 C8 C7 C6 116.5(3) . . ?
 C8 C7 C14 122.4(3) . . ?
 C4 C13 H13A 109.5 . . ?
 C4 C13 H13B 109.5 . . ?
 C4 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C7 C14 H14A 109.5 . . ?
 C7 C14 H14B 109.5 . . ?
 C7 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?


_olex2_exptl_crystal_mounting_method 'MiTeGen MicroMount w/ mineral oil'
_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 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.714
