#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:45:17 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180275 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/61/7116126.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7116126
loop_
_publ_author_name
'Giannis S. Papaefstathiou'
'Andrew J. E. Duncan'
'Leonard R. MacGillivray'
_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/[σ²(Fo²)+(0.0468P)²+1.0750P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c4cc07747d2.cif
_cod_data_source_block           mcg146
_cod_database_code               7116126
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2A N 0.2268(4) 0.61822(17) 0.59993(17) 0.0585(8) Uani 0.906(4) 1 d . P A 1
C12A C 0.2047(5) 0.6506(2) 0.6772(2) 0.0706(9) Uani 0.906(4) 1 d . P A 1
H12A H 0.2076 0.6992 0.6788 0.085 Uiso 0.906(4) 1 calc R P A 1
C11A C 0.1781(5) 0.6154(2) 0.7540(2) 0.0763(11) Uani 0.906(4) 1 d . P A 1
H11A H 0.1657 0.6395 0.8068 0.092 Uiso 0.906(4) 1 calc R P A 1
C10A C 0.1703(5) 0.5442(2) 0.7508(2) 0.0789(11) Uani 0.906(4) 1 d . P A 1
H10A H 0.1503 0.5192 0.8014 0.095 Uiso 0.906(4) 1 calc R P A 1
C9A C 0.1920(4) 0.5094(2) 0.6724(2) 0.0656(9) Uani 0.906(4) 1 d . P A 1
H9A H 0.1879 0.4608 0.6697 0.079 Uiso 0.906(4) 1 calc R P A 1
C8A C 0.2202(4) 0.54840(17) 0.59766(19) 0.0524(7) Uani 0.906(4) 1 d . P A 1
C7A C 0.2487(4) 0.51683(15) 0.51120(19) 0.0544(7) Uani 0.906(4) 1 d . P A 1
H7A H 0.2721 0.5479 0.4668 0.065 Uiso 0.906(4) 1 calc R P A 1
C6A C 0.2453(4) 0.45025(15) 0.48899(19) 0.0537(7) Uani 0.906(4) 1 d . P A 1
H6A H 0.2209 0.4183 0.5321 0.064 Uiso 0.906(4) 1 calc R P A 1
N1A N 0.2599(4) 0.35265(13) 0.39095(17) 0.0576(7) Uani 0.906(4) 1 d . P A 1
C5A C 0.2771(4) 0.42233(15) 0.40177(18) 0.0489(7) Uani 0.906(4) 1 d . P A 1
C4A C 0.3209(5) 0.46412(18) 0.3326(2) 0.0576(8) Uani 0.906(4) 1 d . P A 1
H4A H 0.337(4) 0.5152(17) 0.342(2) 0.069 Uiso 0.906(4) 1 d R P A 1
C1A C 0.2866(5) 0.3246(2) 0.3117(3) 0.0710(10) Uani 0.906(4) 1 d . P A 1
H1A H 0.277(5) 0.275(2) 0.310(2) 0.085 Uiso 0.906(4) 1 d R P A 1
C3A C 0.3470(5) 0.4336(2) 0.2528(2) 0.0672(9) Uani 0.906(4) 1 d . P A 1
H3A H 0.3764 0.4611 0.2062 0.081 Uiso 0.906(4) 1 calc R P A 1
C2A C 0.3298(5) 0.3629(2) 0.2416(2) 0.0720(10) Uani 0.906(4) 1 d . P A 1
H2A H 0.3471 0.3415 0.1878 0.086 Uiso 0.906(4) 1 calc R P A 1
N2B N 0.220(3) 0.6426(14) 0.5999(11) 0.066(8) Uiso 0.094(4) 1 d . P A 2
C12B C 0.286(4) 0.6806(10) 0.6799(16) 0.069(7) Uiso 0.094(4) 1 d G P A 2
H12B H 0.3217 0.7269 0.6761 0.083 Uiso 0.094(4) 1 calc R P A 2
C11B C 0.298(3) 0.6495(12) 0.7657(12) 0.074(7) Uiso 0.094(4) 1 d G P A 2
H11B H 0.3415 0.6750 0.8192 0.089 Uiso 0.094(4) 1 calc R P A 2
C10B C 0.244(3) 0.5804(12) 0.7714(13) 0.068(7) Uiso 0.094(4) 1 d G P A 2
H10B H 0.2520 0.5596 0.8287 0.082 Uiso 0.094(4) 1 calc R P A 2
C9B C 0.179(3) 0.5423(10) 0.6913(18) 0.063(7) Uiso 0.094(4) 1 d G P A 2
H9B H 0.1428 0.4961 0.6951 0.075 Uiso 0.094(4) 1 calc R P A 2
C8B C 0.167(2) 0.5735(13) 0.6056(13) 0.064(7) Uiso 0.094(4) 1 d DG P A 2
C7B C 0.097(3) 0.5406(11) 0.5130(14) 0.063(6) Uiso 0.094(4) 1 d D P A 2
H7B H 0.1338 0.5669 0.4633 0.076 Uiso 0.094(4) 1 calc R P A 2
C6B C 0.108(3) 0.4630(11) 0.4995(15) 0.058(6) Uiso 0.094(4) 1 d D P A 2
H6B H 0.1681 0.4403 0.5573 0.069 Uiso 0.094(4) 1 calc R P A 2
N1B N 0.182(3) 0.3669(11) 0.4061(17) 0.073(7) Uiso 0.094(4) 1 d . P A 2
C5B C 0.191(2) 0.4386(12) 0.4210(12) 0.066(6) Uiso 0.094(4) 1 d DG P A 2
C4B C 0.269(4) 0.4816(10) 0.3643(18) 0.075(8) Uiso 0.094(4) 1 d G P A 2
H4B H 0.2753 0.5296 0.3743 0.090 Uiso 0.094(4) 1 calc R P A 2
C3B C 0.338(4) 0.4528(16) 0.2927(18) 0.076(9) Uiso 0.094(4) 1 d G P A 2
H3B H 0.3907 0.4816 0.2547 0.091 Uiso 0.094(4) 1 calc R P A 2
C2B C 0.330(4) 0.3811(17) 0.2777(16) 0.082(9) Uiso 0.094(4) 1 d G P A 2
H2B H 0.3759 0.3618 0.2298 0.099 Uiso 0.094(4) 1 calc R P A 2
C1B C 0.252(4) 0.3381(11) 0.334(2) 0.076(9) Uiso 0.094(4) 1 d G P A 2
H1B H 0.2456 0.2901 0.3245 0.091 Uiso 0.094(4) 1 calc R P A 2
O1 O 0.2658(3) 0.70738(10) 0.46436(13) 0.0673(5) Uani 1 1 d . . . .
H1 H 0.2512 0.6755 0.4991 0.081 Uiso 1 1 calc R . . .
O2 O -0.0623(3) 0.66969(12) 0.34458(15) 0.0819(6) Uani 1 1 d . . . .
H2 H -0.0464 0.6856 0.3970 0.098 Uiso 1 1 calc R . . .
C13 C 0.2668(4) 0.68058(14) 0.37813(18) 0.0574(7) Uani 1 1 d . . . .
C14 C 0.1024(4) 0.66391(14) 0.31923(19) 0.0609(7) Uani 1 1 d . . . .
C18 C 0.4287(4) 0.67403(16) 0.3486(2) 0.0683(8) Uani 1 1 d . . . .
H18 H 0.5388 0.6858 0.3880 0.082 Uiso 1 1 calc R . . .
C15 C 0.1018(5) 0.63970(17) 0.2311(2) 0.0741(8) Uani 1 1 d . . . .
H15 H -0.0080 0.6279 0.1915 0.089 Uiso 1 1 calc R . . .
C17 C 0.4288(5) 0.65008(18) 0.2606(2) 0.0788(9) Uani 1 1 d . . . .
H17 H 0.5385 0.6454 0.2410 0.095 Uiso 1 1 calc R . . .
C16 C 0.2658(5) 0.63324(18) 0.2025(2) 0.0790(9) Uani 1 1 d . . . .
H16 H 0.2655 0.6173 0.1433 0.095 Uiso 1 1 calc R . . .
O4 O -0.1098(3) 0.33658(10) 0.03513(14) 0.0698(6) Uani 1 1 d . . . .
H4 H -0.1277 0.2943 0.0319 0.084 Uiso 1 1 calc R . . .
O3 O 0.1100(3) 0.23207(9) -0.00447(14) 0.0713(6) Uani 1 1 d . . . .
H3 H 0.1605 0.2081 -0.0376 0.086 Uiso 1 1 calc R . . .
C19 C 0.1740(4) 0.29925(13) -0.00259(17) 0.0539(6) Uani 1 1 d . . . .
C20 C 0.0581(4) 0.35085(14) 0.01843(18) 0.0565(7) Uani 1 1 d . . . .
C21 C 0.1165(5) 0.41909(15) 0.0230(2) 0.0734(8) Uani 1 1 d . . . .
H21 H 0.0410 0.4539 0.0380 0.088 Uiso 1 1 calc R . . .
C24 C 0.3435(4) 0.31678(15) -0.0179(2) 0.0667(8) Uani 1 1 d . . . .
H24 H 0.4214 0.2820 -0.0307 0.080 Uiso 1 1 calc R . . .
C23 C 0.3984(5) 0.38518(17) -0.0145(2) 0.0813(9) Uani 1 1 d . . . .
H23 H 0.5125 0.3969 -0.0258 0.098 Uiso 1 1 calc R . . .
C22 C 0.2836(5) 0.43679(17) 0.0059(2) 0.0845(10) Uani 1 1 d . . . .
H22 H 0.3198 0.4834 0.0080 0.101 Uiso 1 1 calc R . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8A N2A C12A 118.2(3) . .
N2A C12A C11A 123.1(3) . .
C10A C11A C12A 118.3(3) . .
C11A C10A C9A 120.1(3) . .
C10A C9A C8A 118.5(3) . .
N2A C8A C9A 121.9(3) . .
N2A C8A C7A 114.8(3) . .
C9A C8A C7A 123.3(3) . .
C6A C7A C8A 128.1(3) . .
C7A C6A C5A 125.2(3) . .
C5A N1A C1A 118.2(3) . .
N1A C5A C6A 115.9(2) . .
N1A C5A C4A 120.8(3) . .
C4A C5A C6A 123.3(3) . .
C3A C4A C5A 119.4(3) . .
N1A C1A C2A 123.6(3) . .
C2A C3A C4A 119.9(3) . .
C1A C2A C3A 118.1(3) . .
C12B N2B C8B 120.0 . .
C11B C12B N2B 120.0 . .
C10B C11B C12B 120.0 . .
C11B C10B C9B 120.0 . .
C8B C9B C10B 120.0 . .
N2B C8B C7B 113(2) . .
C9B C8B N2B 120.0 . .
C9B C8B C7B 127(2) . .
C8B C7B C6B 121.1(19) . .
C8B C7B C6B 106.4(14) . 3_566
C6B C7B C6B 91(2) 3_566 .
C7B C6B C7B 89(2) 3_566 .
C7B C6B C5B 117.7(15) 3_566 .
C7B C6B C5B 117.0(19) . .
C5B N1B C1B 120.0 . .
N1B C5B C6B 114.6(18) . .
C4B C5B C6B 125.4(18) . .
C4B C5B N1B 120.0 . .
C5B C4B C3B 120.0 . .
C2B C3B C4B 120.0 . .
C3B C2B C1B 120.0 . .
C2B C1B N1B 120.0 . .
O1 C13 C14 119.5(2) . .
C18 C13 O1 120.5(3) . .
C18 C13 C14 119.9(3) . .
O2 C14 C13 122.5(3) . .
O2 C14 C15 117.7(3) . .
C13 C14 C15 119.8(3) . .
C13 C18 C17 120.5(3) . .
C16 C15 C14 119.5(3) . .
C16 C17 C18 119.5(3) . .
C17 C16 C15 120.8(3) . .
O3 C19 C20 116.1(2) . .
O3 C19 C24 123.8(2) . .
C24 C19 C20 120.2(2) . .
O4 C20 C19 122.8(2) . .
O4 C20 C21 118.6(3) . .
C21 C20 C19 118.6(3) . .
C22 C21 C20 121.3(3) . .
C23 C24 C19 120.4(3) . .
C24 C23 C22 119.7(3) . .
C21 C22 C23 119.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2A C12A 1.344(4) .
N2A C8A 1.337(4) .
C12A C11A 1.374(5) .
C11A C10A 1.363(5) .
C10A C9A 1.379(5) .
C9A C8A 1.389(4) .
C8A C7A 1.473(4) .
C7A C6A 1.315(4) .
C6A C5A 1.465(4) .
N1A C5A 1.346(4) .
N1A C1A 1.346(4) .
C5A C4A 1.393(4) .
C4A C3A 1.371(5) .
C1A C2A 1.366(5) .
C3A C2A 1.366(5) .
N2B C12B 1.3900 .
N2B C8B 1.3900 .
C12B C11B 1.3900 .
C11B C10B 1.3900 .
C10B C9B 1.3900 .
C9B C8B 1.3900 .
C8B C7B 1.500(10) .
C7B C6B 1.502(7) 3_566
C7B C6B 1.503(10) .
C6B C7B 1.502(7) 3_566
C6B C5B 1.505(10) .
N1B C5B 1.3900 .
N1B C1B 1.3900 .
C5B C4B 1.3900 .
C4B C3B 1.3900 .
C3B C2B 1.3900 .
C2B C1B 1.3900 .
O1 C13 1.380(3) .
O2 C14 1.365(3) .
C13 C14 1.384(4) .
C13 C18 1.376(4) .
C14 C15 1.386(4) .
C18 C17 1.383(4) .
C15 C16 1.384(4) .
C17 C16 1.372(5) .
O4 C20 1.357(3) .
O3 C19 1.369(3) .
C19 C20 1.391(4) .
C19 C24 1.373(4) .
C20 C21 1.374(4) .
C21 C22 1.367(4) .
C24 C23 1.369(4) .
C23 C22 1.383(5) .
