#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/20/7222005.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_7222005
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         '2(C10 H6 O3), C10 H8 N2'
_chemical_formula_sum            'C30 H20 N2 O6'
_chemical_formula_weight         504.48
_chemical_melting_point          456.9
_chemical_name_common            lawsone-bipyridyl
_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                 96.131(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6360(3)
_cell_length_b                   4.7798(1)
_cell_length_c                   23.0987(9)
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1167.57(6)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6685
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0390
_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)+(0.0546P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1623
_reflns_number_total             2626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01644d2.cif
_cod_data_source_block           se1202
_cod_depositor_comments
'Adding full bibliography for 7222005--7222008.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7222005
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
O1 O 0.81421(8) 0.0814(2) 0.15735(4) 0.0413(3) Uani 1 1 d .
O2 O 0.93377(8) 0.19587(19) 0.06175(4) 0.0424(3) Uani 1 1 d .
H2 H 0.8704 0.2718 0.0739 0.051 Uiso 1 1 calc R
O3 O 1.23640(8) -0.4759(2) 0.12303(4) 0.0460(3) Uani 1 1 d .
C1 C 0.90989(11) -0.0524(3) 0.15086(5) 0.0313(3) Uani 1 1 d .
C2 C 0.97814(11) -0.0013(3) 0.09890(5) 0.0322(3) Uani 1 1 d .
C3 C 1.08094(11) -0.1518(3) 0.08943(6) 0.0349(3) Uani 1 1 d .
H3 H 1.1181 -0.1230 0.0543 0.042 Uiso 1 1 calc R
C4 C 1.13702(11) -0.3555(3) 0.13063(6) 0.0341(3) Uani 1 1 d .
C5 C 1.07179(11) -0.4142(3) 0.18335(5) 0.0309(3) Uani 1 1 d .
C6 C 1.12056(12) -0.6139(3) 0.22335(6) 0.0378(3) Uani 1 1 d .
H6 H 1.1953 -0.7129 0.2170 0.045 Uiso 1 1 calc R
C7 C 1.06033(12) -0.6690(3) 0.27242(6) 0.0425(4) Uani 1 1 d .
H7 H 1.0941 -0.8051 0.2998 0.051 Uiso 1 1 calc R
C8 C 0.95095(13) -0.5263(3) 0.28171(6) 0.0425(4) Uani 1 1 d .
H8 H 0.9098 -0.5655 0.3153 0.051 Uiso 1 1 calc R
C9 C 0.90119(12) -0.3262(3) 0.24215(6) 0.0380(3) Uani 1 1 d .
H9 H 0.8262 -0.2284 0.2487 0.046 Uiso 1 1 calc R
C10 C 0.96171(11) -0.2695(3) 0.19285(5) 0.0309(3) Uani 1 1 d .
N1 N 0.73640(9) 0.5201(2) 0.05762(5) 0.0376(3) Uani 1 1 d .
C11 C 0.63037(13) 0.5585(3) 0.08281(6) 0.0415(4) Uani 1 1 d .
H11 H 0.6193 0.4537 0.1168 0.050 Uiso 1 1 calc R
C12 C 0.53615(13) 0.7422(3) 0.06209(6) 0.0376(4) Uani 1 1 d .
H12 H 0.4626 0.7621 0.0817 0.045 Uiso 1 1 calc R
C13 C 0.54934(11) 0.8987(3) 0.01214(5) 0.0315(3) Uani 1 1 d .
C14 C 0.65842(12) 0.8537(3) -0.01443(6) 0.0417(4) Uani 1 1 d .
H14 H 0.6714 0.9515 -0.0491 0.050 Uiso 1 1 calc R
C15 C 0.74810(13) 0.6669(3) 0.00955(6) 0.0422(4) Uani 1 1 d .
H15 H 0.8224 0.6415 -0.0093 0.051 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_3
C2 O2 H2 109.5 .
O1 C1 C10 122.68(12) .
O1 C1 C2 119.77(12) .
C10 C1 C2 117.55(11) .
O2 C2 C3 120.89(12) .
O2 C2 C1 117.91(11) .
C3 C2 C1 121.20(12) .
C2 C3 C4 122.57(12) .
C2 C3 H3 118.7 .
C4 C3 H3 118.7 .
O3 C4 C3 121.39(12) .
O3 C4 C5 120.61(12) .
C3 C4 C5 118.00(11) .
C6 C5 C10 119.67(12) .
C6 C5 C4 119.94(12) .
C10 C5 C4 120.38(12) .
C7 C6 C5 120.14(13) .
C7 C6 H6 119.9 .
C5 C6 H6 119.9 .
C8 C7 C6 120.16(13) .
C8 C7 H7 119.9 .
C6 C7 H7 119.9 .
C7 C8 C9 120.33(13) .
C7 C8 H8 119.8 .
C9 C8 H8 119.8 .
C8 C9 C10 119.68(13) .
C8 C9 H9 120.2 .
C10 C9 H9 120.2 .
C9 C10 C5 120.01(12) .
C9 C10 C1 119.86(11) .
C5 C10 C1 120.12(12) .
C15 N1 C11 116.72(12) .
N1 C11 C12 123.53(13) .
N1 C11 H11 118.2 .
C12 C11 H11 118.2 .
C11 C12 C13 119.67(13) .
C11 C12 H12 120.2 .
C13 C12 H12 120.2 .
C14 C13 C12 116.49(12) .
C14 C13 C13 121.51(15) 3_675
C12 C13 C13 122.00(14) 3_675
C15 C14 C13 119.90(13) .
C15 C14 H14 120.1 .
C13 C14 H14 120.1 .
N1 C15 C14 123.67(13) .
N1 C15 H15 118.2 .
C14 C15 H15 118.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2245(14) .
O2 C2 1.3269(14) .
O2 H2 0.8400 .
O3 C4 1.2325(14) .
C1 C10 1.4857(18) .
C1 C2 1.4876(18) .
C2 C3 1.3463(17) .
C3 C4 1.4449(19) .
C3 H3 0.9500 .
C4 C5 1.4912(18) .
C5 C6 1.3897(18) .
C5 C10 1.3973(17) .
C6 C7 1.3856(19) .
C6 H6 0.9500 .
C7 C8 1.3851(19) .
C7 H7 0.9500 .
C8 C9 1.3880(19) .
C8 H8 0.9500 .
C9 C10 1.3931(18) .
C9 H9 0.9500 .
N1 C15 1.3303(17) .
N1 C11 1.3357(17) .
C11 C12 1.3791(19) .
C11 H11 0.9500 .
C12 C13 1.3946(18) .
C12 H12 0.9500 .
C13 C14 1.3859(18) .
C13 C13 1.493(2) 3_675
C14 C15 1.3789(19) .
C14 H14 0.9500 .
C15 H15 0.9500 .
