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_7116125
_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'
_chemical_name_systematic
;
 1,2-dihydroxybenzene, 1,2-bis(2-pyridyl)ethylene
;
_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                 102.277(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3687(7)
_cell_length_b                   19.169(2)
_cell_length_c                   14.7014(15)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2029.1(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      190.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16490
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.771
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0897P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3329
_reflns_number_total             4648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07747d2.cif
_cod_data_source_block           mcg466
_cod_database_code               7116125
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.044) H2(0.049) H3(0.049) H4(0.042) H6(0.035) H7(0.034)
 H9(0.036) H10(0.041) H11(0.043) H12(0.042) H15(0.042) H16(0.049) H17(0.049)
 H18(0.046) H21(0.041) H22(0.048) H23(0.048) H24(0.042)
 Fixed X: H1(0.2926) H2(0.3399) H3(0.3575) H4(0.3181) H6(0.2244) H7(0.2802)
 H9(0.1669) H10(0.1176) H11(0.1432) H12(0.2221) H15(-0.0517) H16(-0.0502)
 H17(0.2329) H18(0.5095) H21(0.9222) H22(1.0142) H23(0.8159) H24(0.5296)
 Fixed Y: H1(0.1963) H2(0.1333) H3(0.0113) H4(-0.0441) H6(0.0494) H7(-0.0831)
 H9(0.0164) H10(-0.0322) H11(-0.1539) H12(-0.2214) H15(0.1877) H16(0.1499)
 H17(0.122) H18(0.1308) H21(0.2815) H22(0.3983) H23(0.484) H24(0.4525)
 Fixed Z: H1(0.8131) H2(0.6853) H3(0.6955) H4(0.8313) H6(1.0327) H7(0.9697)
 H9(1.1606) H10(1.2988) H11(1.3205) H12(1.2043) H15(1.1053) H16(1.2561)
 H17(1.3564) H18(1.3047) H21(0.959) H22(0.9671) H23(1.0034) H24(1.0345)
;
_shelx_res_checksum              43386
_olex2_submission_special_instructions 'No special instructions were received'