#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:45:17 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180275 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/61/7116127.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_7116127
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         '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/[σ²(Fo²)+(0.1084P)²+0.0953P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c4cc07747d2.cif
_cod_data_source_block           mcg1323
_cod_database_code               7116127
#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   0.990
_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)
;
_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, -z'
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
N1 N 1.50990(16) 0.80656(16) 0.13000(14) 0.0493(5) Uani 1 1 d .
N2 N 1.42774(16) 1.07386(17) 0.22587(14) 0.0548(5) Uani 1 1 d .
C16 C 1.3264(2) 0.7992(2) 0.01210(18) 0.0508(5) Uani 1 1 d .
H16 H 1.2873 0.8281 -0.0345 0.061 Uiso 1 1 calc R
C21 C 1.2922(2) 1.0867(2) 0.0791(2) 0.0623(7) Uani 1 1 d .
H21 H 1.2758 1.0907 0.0115 0.075 Uiso 1 1 calc R
N4 N 1.36731(18) 0.30528(18) 0.53146(16) 0.0594(5) Uani 1 1 d .
C4 C 1.3764(3) 0.4154(2) 0.2385(2) 0.0684(7) Uani 1 1 d .
H4 H 1.3083 0.4151 0.2600 0.082 Uiso 1 1 calc R
N3 N 1.58253(19) 0.42490(18) 0.28178(16) 0.0622(5) Uani 1 1 d .
C9 C 1.1921(2) 0.3518(2) 0.46256(19) 0.0609(6) Uani 1 1 d .
H9 H 1.1588 0.3997 0.4349 0.073 Uiso 1 1 calc R
H6A H 0.890(3) 1.016(3) 0.177(3) 0.106(11) Uiso 1 1 d D
H5 H 0.6753(17) 0.868(3) 0.197(3) 0.096(11) Uiso 1 1 d D
H2A H 0.811(3) 0.018(3) 0.3730(18) 0.112(13) Uiso 1 1 d D
H1A H 0.5831(18) 0.079(3) 0.305(2) 0.092(10) Uiso 1 1 d D
H4A H 0.721(3) 0.377(3) 0.341(3) 0.105(12) Uiso 1 1 d D
H3A H 0.779(3) 0.158(3) 0.271(2) 0.100(11) Uiso 1 1 d D
O1 O 0.65625(15) 0.08078(15) 0.32941(12) 0.0599(4) Uani 1 1 d D
O2 O 0.85948(16) 0.05323(18) 0.43537(16) 0.0724(5) Uani 1 1 d D
C25 C 0.7945(2) 0.1076(2) 0.49290(18) 0.0544(6) Uani 1 1 d .
C26 C 0.6907(2) 0.1240(2) 0.44107(18) 0.0530(6) Uani 1 1 d .
C27 C 0.6298(3) 0.1828(3) 0.5021(2) 0.0766(8) Uani 1 1 d .
H27 H 0.5611 0.1956 0.4675 0.092 Uiso 1 1 calc R
C30 C 0.8345(3) 0.1479(3) 0.6050(2) 0.0742(8) Uani 1 1 d .
H30 H 0.9041 0.1369 0.6402 0.089 Uiso 1 1 calc R
C28 C 0.6699(3) 0.2226(3) 0.6137(2) 0.0947(10) Uani 1 1 d .
H28 H 0.6281 0.2620 0.6546 0.114 Uiso 1 1 calc R
C29 C 0.7713(3) 0.2044(3) 0.6647(2) 0.0909(10) Uani 1 1 d .
H29 H 0.7976 0.2305 0.7403 0.109 Uiso 1 1 calc R
O5 O 0.75253(16) 0.89770(15) 0.21705(14) 0.0623(5) Uani 1 1 d D
C20 C 1.40179(19) 1.07779(18) 0.12751(17) 0.0452(5) Uani 1 1 d .
C18 C 1.52778(19) 0.94632(18) 0.04487(16) 0.0427(5) Uani 1 1 d .
H18 H 1.6143 0.9618 0.0793 0.051 Uiso 1 1 calc R
O6 O 0.93540(16) 0.97570(16) 0.14961(17) 0.0717(5) Uani 1 1 d D
C17 C 1.45176(19) 0.84716(18) 0.06258(16) 0.0432(5) Uani 1 1 d .
C19 C 1.49863(18) 1.06732(18) 0.07522(16) 0.0426(5) Uani 1 1 d .
H19 H 1.5736 1.1342 0.1219 0.051 Uiso 1 1 calc R
C37 C 0.9040(2) 0.8619(2) 0.14185(18) 0.0543(6) Uani 1 1 d .
C38 C 0.8094(2) 0.8184(2) 0.17518(17) 0.0512(6) Uani 1 1 d .
C15 C 1.2606(2) 0.7088(2) 0.0313(2) 0.0601(6) Uani 1 1 d .
H15 H 1.1769 0.6756 -0.0023 0.072 Uiso 1 1 calc R
C14 C 1.3206(3) 0.6685(2) 0.1010(2) 0.0656(7) Uani 1 1 d .
H14 H 1.2783 0.6080 0.1160 0.079 Uiso 1 1 calc R
C13 C 1.4438(2) 0.7190(2) 0.1478(2) 0.0606(6) Uani 1 1 d .
H13 H 1.4838 0.6909 0.1947 0.073 Uiso 1 1 calc R
C42 C 0.9669(2) 0.7880(3) 0.0998(2) 0.0691(7) Uani 1 1 d .
H42 H 1.0298 0.8162 0.0766 0.083 Uiso 1 1 calc R
C24 C 1.3432(2) 1.0763(2) 0.2746(2) 0.0660(7) Uani 1 1 d .
H24 H 1.3607 1.0727 0.3424 0.079 Uiso 1 1 calc R
C39 C 0.7807(2) 0.7040(2) 0.16868(19) 0.0616(6) Uani 1 1 d .
H39 H 0.7184 0.6754 0.1923 0.074 Uiso 1 1 calc R
C23 C 1.2323(2) 1.0839(3) 0.2301(2) 0.0734(8) Uani 1 1 d .
H23 H 1.1759 1.0851 0.2666 0.088 Uiso 1 1 calc R
C22 C 1.2072(2) 1.0895(3) 0.1313(2) 0.0748(8) Uani 1 1 d .
H22 H 1.1330 1.0952 0.0991 0.090 Uiso 1 1 calc R
C41 C 0.9362(3) 0.6730(3) 0.0924(2) 0.0727(8) Uani 1 1 d .
H41 H 0.9783 0.6235 0.0637 0.087 Uiso 1 1 calc R
C40 C 0.8444(3) 0.6312(2) 0.1270(2) 0.0699(7) Uani 1 1 d .
H40 H 0.8247 0.5536 0.1225 0.084 Uiso 1 1 calc R
O3 O 0.82418(16) 0.14882(15) 0.22896(15) 0.0657(5) Uani 1 1 d D
C8 C 1.3160(2) 0.3716(2) 0.49071(17) 0.0491(5) Uani 1 1 d .
C5 C 1.4835(2) 0.42596(19) 0.31062(18) 0.0509(6) Uani 1 1 d .
C7 C 1.39921(19) 0.4684(2) 0.47548(17) 0.0478(5) Uani 1 1 d .
H7 H 1.3525 0.5037 0.4352 0.057 Uiso 1 1 calc R
C31 C 0.8848(2) 0.2620(2) 0.24315(18) 0.0527(6) Uani 1 1 d .
C6 C 1.49353(19) 0.43161(19) 0.42269(17) 0.0474(5) Uani 1 1 d .
H6 H 1.4943 0.3539 0.4223 0.057 Uiso 1 1 calc R
O4 O 0.7621(2) 0.3320(2) 0.3400(2) 0.0985(8) Uani 1 1 d D
C36 C 0.9736(2) 0.2781(3) 0.1969(2) 0.0691(7) Uani 1 1 d .
H36 H 0.9929 0.2129 0.1575 0.083 Uiso 1 1 calc R
C32 C 0.8534(2) 0.3573(2) 0.2991(2) 0.0666(7) Uani 1 1 d .
C35 C 1.0341(2) 0.3908(3) 0.2087(3) 0.0807(9) Uani 1 1 d .
H35 H 1.0944 0.4017 0.1774 0.097 Uiso 1 1 calc R
C12 C 1.2933(3) 0.2171(2) 0.5435(2) 0.0707(7) Uani 1 1 d .
H12 H 1.3276 0.1697 0.5711 0.085 Uiso 1 1 calc R
C11 C 1.1702(3) 0.1927(3) 0.5175(2) 0.0775(8) Uani 1 1 d .
H11 H 1.1229 0.1310 0.5281 0.093 Uiso 1 1 calc R
C10 C 1.1188(2) 0.2606(3) 0.4760(2) 0.0747(8) Uani 1 1 d .
H10 H 1.0355 0.2456 0.4569 0.090 Uiso 1 1 calc R
C3 C 1.3706(3) 0.4053(3) 0.1351(2) 0.0814(8) Uani 1 1 d .
H3 H 1.2983 0.3965 0.0857 0.098 Uiso 1 1 calc R
C1 C 1.5744(3) 0.4173(2) 0.1802(3) 0.0784(8) Uani 1 1 d .
H1 H 1.6432 0.4183 0.1596 0.094 Uiso 1 1 calc R
C2 C 1.4716(4) 0.4082(3) 0.1059(2) 0.0835(9) Uani 1 1 d .
H2 H 1.4708 0.4042 0.0371 0.100 Uiso 1 1 calc R
C34 C 1.0054(3) 0.4861(3) 0.2662(3) 0.0902(9) Uani 1 1 d .
H34 H 1.0473 0.5626 0.2759 0.108 Uiso 1 1 calc R
C33 C 0.9143(3) 0.4689(3) 0.3100(3) 0.0933(10) Uani 1 1 d .
H33 H 0.8936 0.5340 0.3477 0.112 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
C13 N1 C17 118.0(2) . .
C24 N2 C20 118.0(2) . .
C15 C16 C17 119.7(2) . .
C22 C21 C20 119.7(2) . .
C8 N4 C12 117.0(2) . .
C3 C4 C5 120.0(3) . .
C5 N3 C1 117.0(2) . .
C10 C9 C8 119.4(3) . .
O2 C25 C26 121.3(2) . .
O2 C25 C30 118.9(2) . .
C30 C25 C26 119.8(2) . .
O1 C26 C25 116.4(2) . .
O1 C26 C27 123.9(2) . .
C27 C26 C25 119.7(2) . .
C28 C27 C26 120.3(3) . .
C29 C30 C25 119.8(3) . .
C29 C28 C27 120.0(3) . .
C28 C29 C30 120.4(3) . .
N2 C20 C21 120.97(19) . .
N2 C20 C19 114.76(18) . .
C21 C20 C19 124.2(2) . .
C17 C18 C19 118.09(16) . .
C17 C18 C19 116.52(16) . 2_875
C19 C18 C19 89.21(14) 2_875 .
N1 C17 C16 121.1(2) . .
N1 C17 C18 117.04(18) . .
C16 C17 C18 121.90(19) . .
C20 C19 C18 119.51(17) . 2_875
C20 C19 C18 117.27(17) . .
C18 C19 C18 90.79(14) 2_875 .
O6 C37 C38 120.9(2) . .
O6 C37 C42 119.7(2) . .
C42 C37 C38 119.4(2) . .
O5 C38 C37 115.9(2) . .
C39 C38 O5 124.1(2) . .
C39 C38 C37 120.0(2) . .
C14 C15 C16 118.8(2) . .
C13 C14 C15 118.7(2) . .
N1 C13 C14 123.7(2) . .
C41 C42 C37 120.0(3) . .
N2 C24 C23 123.6(2) . .
C38 C39 C40 120.0(3) . .
C22 C23 C24 118.1(2) . .
C23 C22 C21 119.6(3) . .
C40 C41 C42 120.4(2) . .
C41 C40 C39 120.1(3) . .
N4 C8 C9 122.1(2) . .
N4 C8 C7 116.56(19) . .
C9 C8 C7 121.3(2) . .
C4 C5 C6 122.3(2) . .
N3 C5 C4 121.5(2) . .
N3 C5 C6 116.1(2) . .
C8 C7 C6 119.03(17) . 2_866
C8 C7 C6 115.43(18) . .
C6 C7 C6 88.90(15) . 2_866
C36 C31 O3 119.2(2) . .
C36 C31 C32 120.4(2) . .
C32 C31 O3 120.3(2) . .
C5 C6 C7 119.91(18) . 2_866
C5 C6 C7 119.51(18) . .
C7 C6 C7 91.10(15) . 2_866
C31 C36 C35 120.1(3) . .
O4 C32 C31 116.1(2) . .
O4 C32 C33 125.0(3) . .
C33 C32 C31 118.8(3) . .
C34 C35 C36 119.8(3) . .
N4 C12 C11 123.9(3) . .
C10 C11 C12 118.6(3) . .
C11 C10 C9 119.0(3) . .
C2 C3 C4 119.2(3) . .
N3 C1 C2 124.1(3) . .
C3 C2 C1 118.2(3) . .
C35 C34 C33 119.8(3) . .
C32 C33 C34 121.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C17 1.342(3) .
N1 C13 1.338(3) .
N2 C20 1.342(3) .
N2 C24 1.337(3) .
C16 C17 1.392(3) .
C16 C15 1.374(3) .
C21 C20 1.379(3) .
C21 C22 1.374(4) .
N4 C8 1.338(3) .
N4 C12 1.342(3) .
C4 C5 1.381(3) .
C4 C3 1.371(4) .
N3 C5 1.336(3) .
N3 C1 1.350(4) .
C9 C8 1.387(3) .
C9 C10 1.376(4) .
O1 C26 1.370(3) .
O2 C25 1.362(3) .
C25 C26 1.383(3) .
C25 C30 1.377(3) .
C26 C27 1.374(3) .
C27 C28 1.371(4) .
C30 C29 1.373(4) .
C28 C29 1.368(4) .
O5 C38 1.375(3) .
C20 C19 1.506(3) .
C18 C17 1.501(3) .
C18 C19 1.554(3) 2_875
C18 C19 1.580(3) .
O6 C37 1.359(3) .
C19 C18 1.554(3) 2_875
C37 C38 1.388(3) .
C37 C42 1.384(3) .
C38 C39 1.373(3) .
C15 C14 1.372(4) .
C14 C13 1.366(4) .
C42 C41 1.375(4) .
C24 C23 1.370(4) .
C39 C40 1.382(4) .
C23 C22 1.357(4) .
C41 C40 1.366(4) .
O3 C31 1.373(3) .
C8 C7 1.500(3) .
C5 C6 1.498(3) .
C7 C6 1.550(3) .
C7 C6 1.569(3) 2_866
C31 C36 1.371(3) .
C31 C32 1.372(3) .
C6 C7 1.569(3) 2_866
O4 C32 1.365(3) .
C36 C35 1.378(4) .
C32 C33 1.372(4) .
C35 C34 1.360(4) .
C12 C11 1.371(4) .
C11 C10 1.361(4) .
C3 C2 1.357(4) .
C1 C2 1.366(4) .
C34 C33 1.374(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6A O3 0.878(18) 2.00(2) 2.843(2) 161(3) 1_565
O2 H2A O5 0.819(18) 2.01(2) 2.766(3) 153(3) 1_545
O1 H1A N2 0.858(18) 1.906(19) 2.752(2) 169(3) 1_445
O4 H4A N3 0.830(18) 1.99(2) 2.763(3) 155(3) 1_455
O3 H3A O1 0.884(18) 2.04(2) 2.830(2) 149(3) .
