#------------------------------------------------------------------------------
#$Date: 2020-05-13 02:16:23 +0300 (Wed, 13 May 2020) $
#$Revision: 251989 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038344.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_4038344
loop_
_publ_author_name
'Casola, Kamila Kayser'
'Gomes, Matheus Rick'
'Back, Davi F.'
'Zeni, Gilson'
_publ_section_title
;
 Synthesis of Selenochromenes via Dehydration of Arylalkynols Promoted by
 Iron(III) Chloride and Diorganyl Diselenides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00741
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 Se2'
_chemical_formula_sum            'C22 H16 Se2'
_chemical_formula_weight         438.27
_chemical_melting_point          336
_chemical_name_common
'methylene phenyl phenylselanyl selenochromene'
_chemical_name_systematic
;
4-methylene-2-phenyl-3-(phenylselanyl)-4H-selenochromene
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2019-07-12T15:32:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                110.327(2)
_cell_angle_beta                 92.316(2)
_cell_angle_gamma                96.373(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0078(4)
_cell_length_b                   9.6334(6)
_cell_length_c                   13.8589(8)
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    127(2)
_cell_measurement_theta_max      27.566
_cell_measurement_theta_min      3.146
_cell_volume                     868.78(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      127(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10067
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    4.255
_exptl_absorpt_correction_T_max  0.7007
_exptl_absorpt_correction_T_min  0.35622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0190P)²+0.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0551
_reflns_number_gt                3546
_reflns_number_total             3941
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo0c00741_si_002.cif
_cod_data_source_block           test2_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '336K' was changed to '336'
-- the value should be numeric and without a unit designator.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4038344
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se7 Se 0.24853(3) 0.45478(2) 0.386399(14) 0.01855(6) Uani 1 1 d . . .
Se11 Se 0.48915(3) 0.71686(2) 0.183228(15) 0.02082(6) Uani 1 1 d . . .
C8 C 0.3785(3) 0.58879(19) 0.32980(14) 0.0150(3) Uani 1 1 d . . .
C9 C 0.3376(3) 0.57950(19) 0.23182(14) 0.0148(3) Uani 1 1 d . . .
C11 C 0.5360(3) 0.69145(19) 0.40345(14) 0.0160(4) Uani 1 1 d . . .
C16 C 0.8757(3) 0.7761(2) 0.45024(16) 0.0238(4) Uani 1 1 d . . .
H16 H 1.0057 0.7688 0.4346 0.029 Uiso 1 1 calc R . .
C19 C 0.2946(3) 0.8302(2) 0.16171(14) 0.0176(4) Uani 1 1 d . . .
C17 C 0.7274(3) 0.6825(2) 0.38121(15) 0.0189(4) Uani 1 1 d . . .
H17 H 0.7564 0.6116 0.3181 0.023 Uiso 1 1 calc R . .
C5 C 0.0175(3) 0.41045(19) 0.19783(14) 0.0163(4) Uani 1 1 d . . .
C6 C -0.1604(3) 0.3692(2) 0.13773(15) 0.0211(4) Uani 1 1 d . . .
H6 H -0.1698 0.3844 0.0737 0.025 Uiso 1 1 calc R . .
C4 C 0.0221(3) 0.39292(19) 0.29375(14) 0.0165(4) Uani 1 1 d . . .
C24 C 0.1137(3) 0.8240(2) 0.19874(15) 0.0207(4) Uani 1 1 d . . .
H24 H 0.0774 0.7559 0.2326 0.025 Uiso 1 1 calc R . .
C10 C 0.1905(3) 0.4664(2) 0.15713(14) 0.0165(4) Uani 1 1 d . . .
C15 C 0.8340(3) 0.8801(2) 0.54207(16) 0.0258(4) Uani 1 1 d . . .
H15 H 0.9357 0.9444 0.5894 0.031 Uiso 1 1 calc R . .
C14 C 0.6451(3) 0.8905(2) 0.56493(16) 0.0255(4) Uani 1 1 d . . .
H14 H 0.6169 0.9628 0.6276 0.031 Uiso 1 1 calc R . .
C3 C -0.1398(3) 0.3295(2) 0.32603(16) 0.0219(4) Uani 1 1 d . . .
H3 H -0.1331 0.3173 0.3912 0.026 Uiso 1 1 calc R . .
C20 C 0.3466(3) 0.9303(2) 0.11193(16) 0.0248(4) Uani 1 1 d . . .
H20 H 0.4699 0.9345 0.0861 0.03 Uiso 1 1 calc R . .
C13 C 0.4953(3) 0.7954(2) 0.49641(15) 0.0213(4) Uani 1 1 d . . .
H13 H 0.3657 0.8014 0.5131 0.026 Uiso 1 1 calc R . .
C12 C 0.2115(3) 0.4154(2) 0.05589(15) 0.0255(4) Uani 1 1 d . . .
H12A H 0.1154 0.3429 0.0096 0.031 Uiso 1 1 calc R . .
H12B H 0.3226 0.4516 0.0302 0.031 Uiso 1 1 calc R . .
C23 C -0.0137(3) 0.9183(2) 0.18590(17) 0.0265(4) Uani 1 1 d . . .
H23 H -0.1375 0.9144 0.2111 0.032 Uiso 1 1 calc R . .
C2 C -0.3107(3) 0.2841(2) 0.26318(17) 0.0257(4) Uani 1 1 d . . .
H2 H -0.4201 0.2375 0.2839 0.031 Uiso 1 1 calc R . .
C1 C -0.3210(3) 0.3071(2) 0.16973(16) 0.0251(4) Uani 1 1 d . . .
H1 H -0.4393 0.2799 0.1277 0.03 Uiso 1 1 calc R . .
C21 C 0.2180(4) 1.0237(2) 0.10024(18) 0.0325(5) Uani 1 1 d . . .
H21 H 0.2539 1.0925 0.0668 0.039 Uiso 1 1 calc R . .
C22 C 0.0382(3) 1.0177(2) 0.13671(18) 0.0304(5) Uani 1 1 d . . .
H22 H -0.0496 1.0816 0.128 0.036 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 0 '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
C8 Se7 C4 98.10(8) . . ?
C19 Se11 C9 99.97(8) . . ?
C9 C8 C11 126.11(16) . . ?
C9 C8 Se7 122.22(14) . . ?
C11 C8 Se7 111.46(12) . . ?
C8 C9 C10 124.76(16) . . ?
C8 C9 Se11 117.57(13) . . ?
C10 C9 Se11 117.60(12) . . ?
C17 C11 C13 119.13(17) . . ?
C17 C11 C8 120.14(16) . . ?
C13 C11 C8 120.71(17) . . ?
C15 C16 C17 119.94(19) . . ?
C24 C19 C20 119.86(18) . . ?
C24 C19 Se11 123.47(14) . . ?
C20 C19 Se11 116.52(15) . . ?
C16 C17 C11 120.60(18) . . ?
C4 C5 C6 117.24(17) . . ?
C4 C5 C10 122.96(16) . . ?
C6 C5 C10 119.78(17) . . ?
C1 C6 C5 121.46(19) . . ?
C3 C4 C5 121.32(17) . . ?
C3 C4 Se7 116.89(14) . . ?
C5 C4 Se7 121.79(14) . . ?
C23 C24 C19 119.53(18) . . ?
C12 C10 C5 120.34(17) . . ?
C12 C10 C9 121.54(17) . . ?
C5 C10 C9 118.12(15) . . ?
C14 C15 C16 120.06(18) . . ?
C15 C14 C13 120.28(19) . . ?
C2 C3 C4 120.01(19) . . ?
C21 C20 C19 119.8(2) . . ?
C11 C13 C14 119.97(19) . . ?
C22 C23 C24 120.5(2) . . ?
C3 C2 C1 119.57(19) . . ?
C6 C1 C2 120.26(18) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C23 119.8(2) . . ?
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
Se7 C8 1.9005(18) . ?
Se7 C4 1.9014(18) . ?
Se11 C19 1.9142(19) . ?
Se11 C9 1.9228(17) . ?
C8 C9 1.346(3) . ?
C8 C11 1.484(2) . ?
C9 C10 1.484(2) . ?
C11 C17 1.393(3) . ?
C11 C13 1.393(3) . ?
C16 C15 1.385(3) . ?
C16 C17 1.386(3) . ?
C19 C24 1.389(3) . ?
C19 C20 1.394(3) . ?
C5 C4 1.396(3) . ?
C5 C6 1.408(2) . ?
C5 C10 1.483(3) . ?
C6 C1 1.377(3) . ?
C4 C3 1.392(3) . ?
C24 C23 1.391(3) . ?
C10 C12 1.336(3) . ?
C15 C14 1.380(3) . ?
C14 C13 1.394(3) . ?
C3 C2 1.385(3) . ?
C20 C21 1.385(3) . ?
C23 C22 1.382(3) . ?
C2 C1 1.388(3) . ?
C21 C22 1.379(3) . ?
