Two act as one: unexpected dimers of catechol direct a solid-state [2+2] photodimerization in a six-component hydrogen-bonded assembly
Giannis S. Papaefstathiou; Andrew J. E. Duncan; Leonard R. MacGillivray; Chem.Commun. 50 (2014) 15960–; doi:10.1039/C4cc07747D

data_7116126
_publ_section_title
;
 Two act as one: unexpected dimers of catechol direct a solid-state [2+2]
 photodimerization in a six-component hydrogen-bonded assembly
;
_journal_name_full               Chem.Commun.
_journal_page_first              15960
_journal_paper_doi               10.1039/C4cc07747D
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H6 O2)'
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.43
_chemical_name_common
;
 catechol, 2,2'-bpe, rctt-2,2'-tpcb
;
_chemical_name_systematic
'1,2-dihydroxybenzene, 1,2-bis(2-pyridyl)ethylene,  rctt-tetrakis(2-pyridyl)cyclobutane'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.249(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4665(8)
_cell_length_b                   19.1328(19)
_cell_length_c                   14.8336(15)
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_cell_volume                     2070.8(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
 HKL Denzo, Scalepack (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10870
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.551
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0589
_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/[\s^2^(Fo^2^)+(0.0468P)^2^+1.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2685
_reflns_number_total             3631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07747d2.cif
_cod_data_source_block           mcg146
_cod_database_code               7116126
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H12A(0.085) H11A(0.092) H10A(0.095) H9A(0.079) H7A(0.065)
 H6A(0.064) H4A(0.069) H1A(0.085) H3A(0.081) H2A(0.086) H12B(0.083) H11B(0.089)
 H10B(0.082) H9B(0.075) H7B(0.076) H6B(0.069) H4B(0.09) H3B(0.091) H2B(0.099)
 H1B(0.091) H1(0.081) H2(0.098) H18(0.082) H15(0.089) H17(0.095) H16(0.095)
 H4(0.084) H3(0.086) H21(0.088) H24(0.08) H23(0.098) H22(0.101)
 Fixed X: H12A(0.2076) H11A(0.1657) H10A(0.1503) H9A(0.1879) H7A(0.2721)
 H6A(0.2209) H3A(0.3764) H2A(0.3471) H12B(0.3217) H11B(0.3415) H10B(0.252)
 H9B(0.1428) H7B(0.1338) H6B(0.1681) H4B(0.2753) H3B(0.3907) H2B(0.3759)
 H1B(0.2456) H1(0.2512) H2(-0.0464) H18(0.5388) H15(-0.008) H17(0.5385)
 H16(0.2655) H4(-0.1277) H3(0.1605) H21(0.041) H24(0.4214) H23(0.5125)
 H22(0.3198)
 Fixed Y: H12A(0.6992) H11A(0.6395) H10A(0.5192) H9A(0.4608) H7A(0.5479)
 H6A(0.4183) H3A(0.4611) H2A(0.3415) H12B(0.7269) H11B(0.675) H10B(0.5596)
 H9B(0.4961) H7B(0.5669) H6B(0.4403) H4B(0.5296) H3B(0.4816) H2B(0.3618)
 H1B(0.2901) H1(0.6755) H2(0.6856) H18(0.6858) H15(0.6279) H17(0.6454)
 H16(0.6173) H4(0.2943) H3(0.2081) H21(0.4539) H24(0.282) H23(0.3969)
 H22(0.4834)
 Fixed Z: H12A(0.6788) H11A(0.8068) H10A(0.8014) H9A(0.6697) H7A(0.4668)
 H6A(0.5321) H3A(0.2062) H2A(0.1878) H12B(0.6761) H11B(0.8192) H10B(0.8287)
 H9B(0.6951) H7B(0.4633) H6B(0.5573) H4B(0.3743) H3B(0.2547) H2B(0.2298)
 H1B(0.3245) H1(0.4991) H2(0.397) H18(0.388) H15(0.1915) H17(0.241) H16(0.1433)
 H4(0.0319) H3(-0.0376) H21(0.038) H24(-0.0307) H23(-0.0258) H22(0.008)
;
_shelx_res_checksum              8751
_olex2_submission_special_instructions 'No special instructions were received'