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_7116127
_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         '2(C12 H10 N2), 3(C6 H6 O2)'
_chemical_formula_sum            'C42 H38 N4 O6'
_chemical_formula_weight         694.76
_chemical_name_common            'catechol, 2,2'-tpcb'
_chemical_name_systematic
;
 1,2-dihydroxybenzene, rctt-tetrakis(2-pyridyl)cyclobutane
;
_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   mixed
_audit_creation_date             2014-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                109.918(5)
_cell_angle_beta                 103.137(5)
_cell_angle_gamma                102.958(5)
_cell_formula_units_Z            2
_cell_length_a                   11.9841(12)
_cell_length_b                   12.6106(13)
_cell_length_c                   13.7902(14)
_cell_measurement_reflns_used    5559
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      1.00
_cell_volume                     1801.6(3)
_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)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.997
_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  0.0192
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.874
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9665
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.096
_diffrn_reflns_theta_min         1.665
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             732
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Nitromethane'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         5711
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0512
_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^)+(0.1084P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4235
_reflns_number_total             5711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07747d2.cif
_cod_data_source_block           mcg1323
_cod_database_code               7116127
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1A
 0.84 with sigma of 0.02
 O2-H2A
 0.84 with sigma of 0.02
 O3-H3A
 0.84 with sigma of 0.02
 O4-H4A
 0.84 with sigma of 0.02
 O5-H5
 0.84 with sigma of 0.02
 O6-H6A
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C18(H18), C19(H19), C7(H7), C6(H6)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C21(H21), C4(H4), C9(H9), C27(H27), C30(H30), C28(H28), C29(H29),
 C15(H15), C14(H14), C13(H13), C42(H42), C24(H24), C39(H39), C23(H23), C22(H22),
  C41(H41), C40(H40), C36(H36), C35(H35), C12(H12), C11(H11), C10(H10), C3(H3),
 C1(H1), C2(H2), C34(H34), C33(H33)
;
_shelx_res_checksum              35709
_olex2_submission_special_instructions 'No special instructions were received'