Dimethyldihydropyrene-cyclophanediene photochromic couple functionalized with terpyridyl metal complexes as multi-addressable redox- and photo-switches.
Bakkar, Assil; Cobo, Saioa; Lafolet, Frédéric; Roldan, Diego; Jacquet, Margot; Bucher, Christophe; Royal, Guy; Saint-Aman, Eric; Dalton transactions (Cambridge, England : 2003) 45 (2016) 13700–13708; doi:10.1039/c6dt00843g

data_7039522
_publ_section_title
;
 Dimethyldihydropyrene-cyclophanediene photochromic couple functionalized
 with terpyridyl metal complexes as multi-addressable redox- and
 photo-switches.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13700
_journal_page_last               13708
_journal_paper_doi               10.1039/c6dt00843g
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety
'C94 H90 N6 Zn, B F4, 4.33(C H4 O), C0.91 H2.72 B0.5 F1.26 O0.91, 0.49(H2 O), 1.25(O), 0.5(Cl), H2 O0.5, 0.76(F)'
_chemical_formula_sum            'C99.24 H113.02 B1.5 Cl0.5 F6.02 N6 O7.47 Zn'
_chemical_formula_weight         1722.96
_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             2016-02-04
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_audit_update_record
;
2016-04-06 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                103.94(2)
_cell_angle_beta                 91.56(5)
_cell_angle_gamma                91.38(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4857(19)
_cell_length_b                   16.519(3)
_cell_length_c                   30.909(6)
_cell_measurement_reflns_used    28336
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.261
_cell_measurement_theta_min      1.358
_cell_volume                     4696.5(16)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.889
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.1387
_diffrn_reflns_Laue_measured_fraction_full 0.889
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            28336
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.261
_diffrn_reflns_theta_min         1.358
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
R(int) was 0.1459 before and 0.1010 after correction.
The Ratio of minimum to maximum transmission is 0.4929.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1821
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1514
_refine_ls_number_reflns         14791
_refine_ls_number_restraints     1926
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.2038
_refine_ls_R_factor_gt           0.1635
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1648P)^2^+22.8905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3959
_refine_ls_wR_factor_ref         0.4251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10944
_reflns_number_total             14791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt00843g2.cif
_cod_data_source_block           nanny
_cod_depositor_comments          'Adding full bibliography for 7039522.cif.'
_cod_original_cell_volume        4696.4(16)
_cod_original_formula_sum
'C99.24 H113.02 B1.50 Cl0.50 F6.02 N6 O7.47 Zn'
_cod_database_code               7039522
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C30D-C29D
 2.5 with sigma of 0.02
 C32A-C34A
 2.5 with sigma of 0.02
 F3B-B1
 1.3 with sigma of 0.02
 B1-F2B
 1.3 with sigma of 0.02
 B1-F1B
 1.3 with sigma of 0.02
 F4B-B1
 1.3 with sigma of 0.02
 B15A-F3A
 1.3 with sigma of 0.02
 B15A-F2A
 1.3 with sigma of 0.02
 B15A-F1A
 1.3 with sigma of 0.02
 B15A-F4A
 1.3 with sigma of 0.02
 C32C-C31A
 1.5 with sigma of 0.02
 C34C-C31A
 1.5 with sigma of 0.02
 C31A-C33C
 1.5 with sigma of 0.02
 C29C-C27A
 1.5 with sigma of 0.02
 C27A-C30C
 1.5 with sigma of 0.02
 C27A-C28C
 1.5 with sigma of 0.02
 C31B-C33D
 1.5 with sigma of 0.02
 C31B-C34D
 1.5 with sigma of 0.02
 C31B-C32D
 1.5 with sigma of 0.02
 O40-C40
 1.5 with sigma of 0.02
 O39-C39
 1.5 with sigma of 0.02
 B2-F6A
 1.3 with sigma of 0.02
 B2-F7B
 1.3 with sigma of 0.02
 B2-F5A
 1.3 with sigma of 0.02
 B2-F7A
 1.3 with sigma of 0.02
 B2-F8B
 1.3 with sigma of 0.02
 B2-F6B
 1.3 with sigma of 0.02
 B2-F8A
 1.3 with sigma of 0.02
 F2B-F3B
 2.2 with sigma of 0.02
 F2B-F1B
 2.2 with sigma of 0.02
 F2B-F4B
 2.2 with sigma of 0.02
 F1B-F4B
 2.2 with sigma of 0.02
 F1B-F3B
 2.2 with sigma of 0.02
 F3B-F4B
 2.2 with sigma of 0.02
 F2A-F3A
 2.2 with sigma of 0.02
 F3A-F4A
 2.2 with sigma of 0.02
 F3A-F1A
 2.2 with sigma of 0.02
 F1A-F2A
 2.2 with sigma of 0.02
 F1A-F4A
 2.2 with sigma of 0.02
 F2A-F4A
 2.2 with sigma of 0.02
 F6A-F5A
 2.2 with sigma of 0.02
 F5A-F8A
 2.2 with sigma of 0.02
 F5A-F7A
 2.2 with sigma of 0.02
 F8A-F7A
 2.2 with sigma of 0.02
 F8A-F6A
 2.2 with sigma of 0.02
 F6A-F7A
 2.2 with sigma of 0.02
 F5A-F6B
 2.2 with sigma of 0.02
 F5A-F7B
 2.2 with sigma of 0.02
 F5A-F8B
 2.2 with sigma of 0.02
 F6B-F8B
 2.2 with sigma of 0.02
 F8B-F7B
 2.2 with sigma of 0.02
 F6B-F7B
 2.2 with sigma of 0.02
 O44-C44
 1.45 with sigma of 0.02
 C47-O47
 1.45 with sigma of 0.02
 C45-O45
 1.45 with sigma of 0.02
 O42-C42
 1.45 with sigma of 0.02
 C46-O46
 1.45 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C34D) = Uanis(C32B)
Uanis(O45) = Uanis(C45)
5. Others
 Sof(C29B)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30B)=Sof(H30D)=Sof(H30E)=
 Sof(H30F)=Sof(C28B)=Sof(H28G)=Sof(H28H)=Sof(H28I)=1-FVAR(1)
 Sof(C28D)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C30D)=Sof(H30G)=Sof(H30H)=
 Sof(H30I)=Sof(C29D)=Sof(H29G)=Sof(H29H)=Sof(H29I)=FVAR(1)
 Sof(C24D)=Sof(C26D)=Sof(H26G)=Sof(H26H)=Sof(H26I)=Sof(C23D)=Sof(C25D)=
 Sof(H25G)=Sof(H25H)=Sof(H25I)=1-FVAR(2)
 Sof(C23B)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C25B)=Sof(H25D)=
 Sof(H25E)=Sof(H25F)=Sof(C24B)=FVAR(2)
 Sof(C26C)=Sof(H26J)=Sof(H26K)=Sof(H26L)=Sof(C24C)=Sof(C23C)=Sof(C25C)=
 Sof(H25J)=Sof(H25K)=Sof(H25L)=1-FVAR(3)
 Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C24A)=Sof(C26A)=Sof(H26A)=
 Sof(H26B)=Sof(H26C)=Sof(C23A)=FVAR(3)
 Sof(F2B)=Sof(B1)=Sof(F1B)=Sof(F4B)=Sof(F3B)=1-FVAR(4)
 Sof(F4A)=Sof(F3A)=Sof(F1A)=Sof(B15A)=Sof(F2A)=Sof(O43)=Sof(H43)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(4)
 Sof(O50)=Sof(H50A)=Sof(H50B)=1-FVAR(5)
 Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(H47C)=Sof(O47)=Sof(H47)=FVAR(5)
 Sof(O39)=Sof(H39)=Sof(O40)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40)=
 Sof(H40A)=Sof(H40B)=Sof(H40C)=1-FVAR(6)
 Sof(C33C)=Sof(H33G)=Sof(H33H)=Sof(H33I)=Sof(C34C)=Sof(H34G)=Sof(H34H)=
 Sof(H34I)=Sof(C32C)=Sof(H32G)=Sof(H32H)=Sof(H32I)=1-FVAR(7)
 Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C32A)=Sof(H32D)=Sof(H32E)=
 Sof(H32F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=FVAR(7)
 Sof(C30C)=Sof(H30J)=Sof(H30K)=Sof(H30L)=Sof(C29C)=Sof(H29J)=Sof(H29K)=
 Sof(H29L)=Sof(C28C)=Sof(H28J)=Sof(H28K)=Sof(H28L)=1-FVAR(8)
 Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C30A)=Sof(H30A)=Sof(H30B)=
 Sof(H30C)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=FVAR(8)
 Sof(O49A)=1-FVAR(9)
 Sof(O49B)=FVAR(9)
 Sof(C33D)=Sof(H33J)=Sof(H33K)=Sof(H33L)=Sof(C32D)=Sof(H32J)=Sof(H32K)=
 Sof(H32L)=Sof(C34D)=Sof(H34J)=Sof(H34K)=Sof(H34L)=1-FVAR(10)
 Sof(C32B)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33B)=Sof(H33D)=Sof(H33E)=
 Sof(H33F)=Sof(C34B)=Sof(H34A)=Sof(H34B)=Sof(H34C)=FVAR(10)
 Sof(B2)=Sof(F5A)=1-FVAR(11)
 Sof(F7B)=Sof(F6A)=Sof(F7A)=Sof(F8B)=Sof(F6B)=Sof(F8A)=0.5*(1-FVAR(12))
 Sof(Cl1)=FVAR(11)
 Fixed Sof: O41(0.75) H41(0.75) C41(0.75) H41A(0.75) H41B(0.75) H41C(0.75)
 O42(0.75) H42(0.75) O44(0.33333) H44(0.33333) O51(0.25) C42(0.75) H42A(0.75)
 H42B(0.75) H42C(0.75) C44(0.33333) H44A(0.33333) H44B(0.33333) H44C(0.33333)
 O45(0.25) H45(0.25) C45(0.25) H45A(0.25) H45B(0.25) H45C(0.25) O46(0.25)
 H46(0.25) C46(0.25) H46A(0.25) H46B(0.25) H46C(0.25)
6.a Everything fixed:
 H48A, H48B
6.b Free rotating group:
 O50(H50A,H50B)
6.c Aromatic/amide H refined with riding coordinates:
 C3'A(H3'A), C14A(H14A), C5'A(H5'A), C35A(H35A), C13B(H13B), C36A(H36A),
 C5A(H5A), C7A(H7A), C12B(H12B), C7B(H7B), C15B(H15B), C2A(H2A), C14B(H14B),
 C15A(H15A), C11A(H11A), C12A(H12A), C13A(H13A), C35B(H35B), C9A(H9A), C3A(H3A),
  C9B(H9B), C6"B(H6"B), C10B(H10B), C8B(H8B), C36B(H36B), C10A(H10A), C2B(H2B),
 C11B(H11B), C5"A(H5"A), C6"A(H6"A), C5'B(H5'B), C8A(H8A), C3'B(H3'B),
 C4"B(H4"B), C4B(H4B), C3"A(H3"A), C5B(H5B), C3"B(H3"B), C4A(H4A), C3B(H3B),
 C5"B(H5"B), C4"A(H4"A)
6.d Idealised Me refined with everything fixed:
 C28B(H28G,H28H,H28I)
6.e Idealised Me refined as rotating group:
 C25A(H25A,H25B,H25C), C26A(H26A,H26B,H26C), C32B(H32A,H32B,H32C), C33A(H33A,
 H33B,H33C), C33B(H33D,H33E,H33F), C34B(H34A,H34B,H34C), C28A(H28A,H28B,H28C),
 C28D(H28D,H28E,H28F), C30A(H30A,H30B,H30C), C26B(H26D,H26E,H26F), C26D(H26G,
 H26H,H26I), C32A(H32D,H32E,H32F), C29B(H29A,H29B,H29C), C29A(H29D,H29E,H29F),
 C30B(H30D,H30E,H30F), C30D(H30G,H30H,H30I), C29D(H29G,H29H,H29I), C34A(H34D,
 H34E,H34F), C25B(H25D,H25E,H25F), C25D(H25G,H25H,H25I), C26C(H26J,H26K,H26L),
 C25C(H25J,H25K,H25L), C41(H41A,H41B,H41C), C47(H47A,H47B,H47C), C39(H39A,H39B,
 H39C), C43(H43A,H43B,H43C), C33C(H33G,H33H,H33I), C34C(H34G,H34H,H34I),
 C32C(H32G,H32H,H32I), C30C(H30J,H30K,H30L), C29C(H29J,H29K,H29L), C28C(H28J,
 H28K,H28L), C40(H40A,H40B,H40C), C33D(H33J,H33K,H33L), C32D(H32J,H32K,H32L),
 C34D(H34J,H34K,H34L), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C45(H45A,H45B,
 H45C), C46(H46A,H46B,H46C)
6.f Idealised tetrahedral OH refined with everything fixed:
 O41(H41)
6.g Idealised tetrahedral OH refined as rotating group:
 O43(H43), O39(H39), O42(H42), O44(H44), O45(H45), O46(H46), O47(H47)
;
_shelx_res_checksum              6670
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'