Influence of the anion nature on styryl dye crystal packing and feasibility of the direct and back [2 + 2] photocycloaddition reactions without single crystal degradation
Kuz'mina, Lyudmila G.; Vedernikov, Artem I.; Churakov, Andrei V.; Lermontova, Elmira Kh.; Howard, Judith A. K.; Alfimov, Michael V.; Gromov, Sergey P.; CrystEngComm 16 (2014) 5364–; doi:10.1039/c4ce00266k

data_7215803
_publ_section_title
;
 Influence of the anion nature on styryl dye crystal packing and
 feasibility of the direct and back [2 + 2] photocycloaddition reactions
 without single crystal degradation
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              5364
_journal_paper_doi               10.1039/c4ce00266k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'F6 P, C17 H20 N O2'
_chemical_formula_sum            'C17 H21 F6 N O2 P'
_chemical_formula_weight         416.32
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.143(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.106(2)
_cell_length_b                   22.507(7)
_cell_length_c                   11.576(3)
_cell_measurement_reflns_used    827
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      29.737
_cell_measurement_theta_min      3.006
_cell_volume                     1851.4(9)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14757
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         0.90
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.8800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         4884
_refine_ls_number_restraints     525
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                2572
_reflns_number_total             4884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00266k1.cif
_cod_data_source_block           ff
_cod_depositor_comments
'Adding full bibliography for 7215801--7215808.cif.'
_cod_original_cell_volume        1851.5(10)
_cod_database_code               7215803
_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. Restrained distances
 P1-F1 \\sim P1-F2 \\sim P1-F3 \\sim P1-F4 \\sim P1-F5 \\sim P1-F6 \\sim P2-F2'
\\sim P2-F3' \\sim P2-F4' \\sim P2-
 F5' \\sim P2-F6'
 with sigma of 0.02
 F1-F3 \\sim F1-F4 \\sim F1-F5 \\sim F1-F6 \\sim F2-F3 \\sim F2-F4 \\sim F2-F5
\\sim F2-F6 \\sim F3-F4 \\sim F3-F6
 \\sim F4-F5 \\sim F5-F6 \\sim F1-F3' \\sim F1-F4' \\sim F1-F5' \\sim F1-F6'
\\sim F2'-F3' \\sim F2'-F4' \\sim F2'-
 F5' \\sim F2'-F6' \\sim F3'-F4' \\sim F3'-F6' \\sim F4'-F5' \\sim F5'-F6'
 with sigma of 0.02
 N1-C1 \\sim N1-C5 \\sim N1'-C1' \\sim N1'-C5
 with sigma of 0.02
 C1-C2 \\sim C4-C5 \\sim C1'-C2' \\sim C4'-C5
 with sigma of 0.02
 C2-C3 \\sim C3-C4 \\sim C2'-C3' \\sim C3'-C4'
 with sigma of 0.02
 C8-C9 \\sim C8'-C9'
 with sigma of 0.02
 C8-C13 \\sim C8'-C13'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F4') \\sim Ueq, Uanis(F5')
\\sim Ueq, Uanis(F6') \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq,
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(N1') \\sim Ueq, Uanis(C1') \\sim Ueq,
Uanis(C2') \\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C6')
\\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C9') \\sim Ueq,
Uanis(C13') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C17') \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(P2)=Sof(F2')=Sof(F3')=Sof(F4')=Sof(F5')=Sof(F6')=1-FVAR(1)
 Sof(P1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(N1')=Sof(C1')=Sof(H1')=Sof(C2')=Sof(H2')=Sof(C3')=Sof(C4')=Sof(H4')=
 Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=Sof(C8')=Sof(C9')=Sof(H9')=Sof(C13')=
 Sof(H13')=Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=Sof(H5B)=Sof(H10A)=1-FVAR(2)
 Sof(N1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C13)=Sof(H13)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(H5A)=Sof(H10)=
 FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16'(H16C,H16D)
5.b Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C13(H13), C1'(H1'), C2'(H2'),
 C4'(H4'), C6'(H6'), C7'(H7'), C9'(H9'), C13'(H13'), C5(H5A), C5(H5B), C10(H10),
  C10(H10A)
;