#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/20/7222006.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_7222006
loop_
_publ_author_name
'Pallipurath, Anuradha'
'Skelton, Jonathan M.'
'Delori, Amit'
'Duffy, Connor'
'Erxleben, Andrea'
'Jones, William'
_publ_section_title
;
 Crystalline adducts of the Lawsone molecule
 (2-hydroxy-1,4-naphthaquinone): optical properties and computational
 modelling
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              7684
_journal_paper_doi               10.1039/C5CE01644D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C12 H12 N2 2+, 2(C10 H5 O3 1-)'
_chemical_formula_sum            'C32 H22 N2 O6'
_chemical_formula_weight         530.52
_chemical_melting_point          283.1
_chemical_name_common            lawsone-ethylenebipyridine
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-13 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.542(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8157(1)
_cell_length_b                   28.0772(7)
_cell_length_c                   11.2326(3)
_cell_measurement_reflns_used    10367
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     1195.56(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10270
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0588P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2319
_reflns_number_total             4108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01644d2.cif
_cod_data_source_block           se1203
_cod_depositor_comments
'Adding full bibliography for 7222005--7222008.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7222006
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.2355(3) 0.06894(5) -0.14389(10) 0.0288(3) Uani 1 1 d .
H1 H 0.1734 0.0787 -0.0748 0.035 Uiso 1 1 calc R
C11 C 0.3043(4) 0.02320(6) -0.16033(13) 0.0300(4) Uani 1 1 d .
H11 H 0.2872 0.0014 -0.0966 0.036 Uiso 1 1 calc R
C12 C 0.3998(4) 0.00662(6) -0.26751(12) 0.0290(4) Uani 1 1 d .
H12 H 0.4518 -0.0262 -0.2767 0.035 Uiso 1 1 calc R
C13 C 0.4201(4) 0.03815(6) -0.36239(12) 0.0250(3) Uani 1 1 d .
C14 C 0.3505(4) 0.08605(6) -0.34197(13) 0.0308(4) Uani 1 1 d .
H14 H 0.3652 0.1089 -0.4037 0.037 Uiso 1 1 calc R
C15 C 0.2605(5) 0.10017(6) -0.23225(13) 0.0316(4) Uani 1 1 d .
H15 H 0.2151 0.1329 -0.2190 0.038 Uiso 1 1 calc R
C16 C 0.5088(4) 0.02244(6) -0.48047(12) 0.0276(3) Uani 1 1 d .
H16 H 0.5842 0.0460 -0.5326 0.041 Uiso 1 1 calc R
O1 O -0.1604(3) 0.14997(4) -0.04073(9) 0.0347(3) Uani 1 1 d .
O2 O 0.1356(3) 0.07422(4) 0.07792(9) 0.0349(3) Uani 1 1 d .
O3 O -0.2132(3) 0.13767(4) 0.43300(9) 0.0363(3) Uani 1 1 d .
C1 C -0.1651(4) 0.14912(5) 0.06809(12) 0.0240(3) Uani 1 1 d .
C2 C -0.0094(4) 0.10695(6) 0.13799(12) 0.0260(3) Uani 1 1 d .
C3 C -0.0290(4) 0.10515(6) 0.25909(12) 0.0266(3) Uani 1 1 d .
H3 H 0.0700 0.0784 0.3023 0.032 Uiso 1 1 calc R
C4 C -0.1896(4) 0.14120(6) 0.32368(12) 0.0258(3) Uani 1 1 d .
C5 C -0.3281(4) 0.18484(5) 0.25769(12) 0.0230(3) Uani 1 1 d .
C6 C -0.4678(4) 0.22223(6) 0.31797(12) 0.0273(4) Uani 1 1 d .
H6 H -0.4868 0.2195 0.4013 0.033 Uiso 1 1 calc R
C7 C -0.5800(4) 0.26357(6) 0.25779(13) 0.0288(4) Uani 1 1 d .
H7 H -0.6701 0.2892 0.3003 0.035 Uiso 1 1 calc R
C8 C -0.5610(4) 0.26759(6) 0.13536(13) 0.0290(4) Uani 1 1 d .
H8 H -0.6353 0.2961 0.0943 0.035 Uiso 1 1 calc R
C9 C -0.4331(4) 0.22988(5) 0.07340(13) 0.0267(3) Uani 1 1 d .
H9 H -0.4265 0.2322 -0.0107 0.032 Uiso 1 1 calc R
C10 C -0.3139(4) 0.18848(5) 0.13378(11) 0.0227(3) Uani 1 1 d .
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
C11 N1 C15 119.97(14) .
C11 N1 H1 120.0 .
C15 N1 H1 120.0 .
N1 C11 C12 121.63(15) .
N1 C11 H11 119.2 .
C12 C11 H11 119.2 .
C11 C12 C13 119.76(15) .
C11 C12 H12 120.1 .
C13 C12 H12 120.1 .
C12 C13 C14 117.28(14) .
C12 C13 C16 122.43(14) .
C14 C13 C16 120.28(13) .
C15 C14 C13 119.81(15) .
C15 C14 H14 120.1 .
C13 C14 H14 120.1 .
N1 C15 C14 121.53(15) .
N1 C15 H15 119.2 .
C14 C15 H15 119.2 .
C16 C16 C13 124.82(19) 3_654
C16 C16 H16 117.6 3_654
C13 C16 H16 117.6 .
O1 C1 C10 122.27(14) .
O1 C1 C2 119.09(14) .
C10 C1 C2 118.63(12) .
O2 C2 C3 124.28(14) .
O2 C2 C1 116.83(12) .
C3 C2 C1 118.89(14) .
C2 C3 C4 123.68(14) .
C2 C3 H3 118.2 .
C4 C3 H3 118.2 .
O3 C4 C3 121.98(14) .
O3 C4 C5 119.48(14) .
C3 C4 C5 118.53(13) .
C6 C5 C10 119.30(14) .
C6 C5 C4 120.74(13) .
C10 C5 C4 119.96(14) .
C7 C6 C5 120.65(14) .
C7 C6 H6 119.7 .
C5 C6 H6 119.7 .
C6 C7 C8 120.17(15) .
C6 C7 H7 119.9 .
C8 C7 H7 119.9 .
C9 C8 C7 119.72(15) .
C9 C8 H8 120.1 .
C7 C8 H8 120.1 .
C8 C9 C10 120.40(14) .
C8 C9 H9 119.8 .
C10 C9 H9 119.8 .
C9 C10 C5 119.71(14) .
C9 C10 C1 120.17(13) .
C5 C10 C1 120.10(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.328(2) .
N1 C15 1.3359(19) .
N1 H1 0.8800 .
C11 C12 1.378(2) .
C11 H11 0.9500 .
C12 C13 1.394(2) .
C12 H12 0.9500 .
C13 C14 1.395(2) .
C13 C16 1.473(2) .
C14 C15 1.375(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C16 1.333(3) 3_654
C16 H16 0.9500 .
O1 C1 1.2247(16) .
O2 C2 1.3001(18) .
O3 C4 1.2454(17) .
C1 C10 1.478(2) .
C1 C2 1.505(2) .
C2 C3 1.3718(18) .
C3 C4 1.424(2) .
C3 H3 0.9500 .
C4 C5 1.497(2) .
C5 C6 1.388(2) .
C5 C10 1.4028(18) .
C6 C7 1.386(2) .
C6 H6 0.9500 .
C7 C8 1.390(2) .
C7 H7 0.9500 .
C8 C9 1.386(2) .
C8 H8 0.9500 .
C9 C10 1.396(2) .
C9 H9 0.9500 .
