Peculiarities of styryl dyes of the benzoselenazole series crystal packings and their influence on solid phase [2 + 2] photocycloaddition reaction with single crystal retention
Kuz'mina, Lyudmila G.; Vedernikov, Artem I.; Howard, Judith A. K.; Bezzubov, Stanislav I.; Alfimov, Michael V.; Gromov, Sergey P.; CrystEngComm 18 (2016) 7506–; doi:10.1039/C6CE01426G

data_7226323
_publ_section_title
;
 Peculiarities of styryl dyes of the benzoselenazole series crystal
 packings and their influence on solid phase [2 + 2] photocycloaddition
 reaction with single crystal retention
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              7506
_journal_paper_doi               10.1039/C6CE01426G
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'I, C19 H20 N O2 Se, 0.5(C6 H6 O2)'
_chemical_formula_sum            'C22 H23 I N O3 Se'
_chemical_formula_weight         555.27
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_creation_date             2015-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-04-17 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                105.4770(10)
_cell_angle_beta                 97.1060(10)
_cell_angle_gamma                105.1850(10)
_cell_formula_units_Z            4
_cell_length_a                   11.8766(3)
_cell_length_b                   12.7576(4)
_cell_length_c                   15.3353(4)
_cell_measurement_reflns_used    5499
_cell_measurement_temperature    120
_cell_measurement_theta_max      2.40
_cell_measurement_theta_min      26.000
_cell_volume                     2113.78(10)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  SMART-6K
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25381
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4986
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.297
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         11152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0258
_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/[\s^2^(Fo^2^)+(0.0314P)^2^+0.8519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                9573
_reflns_number_total             11152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01426g1.cif
_cod_data_source_block           p-1
_cod_depositor_comments
'Adding full bibliography for 7226322--7226329.cif.'
_cod_database_code               7226323
_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, All O(H) groups
2. Others
 Fixed Sof: H1S(0.12) H2S(0.88) H4S(0.12) H5S(0.88) O3A(0.88) H3AA(0.88)
 O4A(0.88) H4A(0.88) O3B(0.12) O4B(0.12) H3B(0.12) H4B(0.12)
3.a Everything fixed:
 H3B, H4B
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C9A(H9A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C1S(H1S), C2S(H2S), C3S(H3S), C4S(H4S),
 C5S(H5S), C6S(H6S)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C10A(H10D,H10E,
 H10F), C11A(H11D,H11E,H11F), C19A(H19D,H19E,H19F)
3.e Idealised tetrahedral OH refined as rotating group:
 O3A(H3AA), O4A(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'