#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:34:47 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/53/7225372.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_7225372
loop_
_publ_author_name
'Delori, Amit'
'Urquhart, Andrew J.'
'Oswald, Iain D. H.'
_publ_section_title
;
 Supramolecular hair dyes: a new application of cocrystallization
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              5360
_journal_paper_doi               10.1039/C6CE01001F
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         '2(C10 H5 O3), C6 H10 N2'
_chemical_formula_sum            'C26 H20 N2 O6'
_chemical_formula_weight         456.44
_chemical_name_systematic        1,4-Diaminobenzene+lawsone
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.851(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.204(3)
_cell_length_b                   8.573(2)
_cell_length_c                   8.3934(19)
_cell_measurement_reflns_used    4963
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      2.78
_cell_volume                     1021.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4626
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         2.428
_diffrn_source                   INCOATECImuSMo
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            'orangeish brown'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       Block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0726P)²+10.3813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2413
_refine_ls_wR_factor_ref         0.2574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                737
_reflns_number_total             985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01001f2.cif
_cod_data_source_block           p-Phenylenediamine+lawsone
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7225370--7225374.cif.
;
_cod_database_code               7225372
_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. 
;
_shelxl_version_number           2013-3
_shelx_res_file
; 
TITL 1 in C2/m 
CELL 0.71073 14.2038 8.5729 8.3934 90 91.8505 90 
ZERR 2 0.0033 0.002 0.0019 0 0.0129 0 
LATT 7 
SYMM -X,+Y,-Z 
  
SFAC C H N O 
UNIT 52 40 4 12 
  
L.S. 4 
PLAN  1 
TEMP -150.21 
BOND $H 
FMAP 2 
ACTA 
REM <HKL>C:\frames\guest\amit\ad62a\work\New%20folder\1.hkl</HKL> 
  
WGHT    0.072600   10.381301 
EXTI    0.010629 
FVAR       0.13175 
C1    1    0.189226    0.080745    0.237215    11.00000    0.01900    0.03594 = 
         0.03174    0.00187    0.00500   -0.00244 
AFIX  43 
PART 1 
H1    2    0.208357    0.135496    0.145328    10.50000   -1.20000 
AFIX   0 
PART 0 
C2    1    0.159988    0.168459    0.377657    11.00000    0.02484    0.02774 = 
         0.03774    0.00551    0.00106    0.00175 
C3    1    0.128847    0.081466    0.521002    11.00000    0.01702    0.03374 = 
         0.03240   -0.00250    0.00508    0.00317 
C4    1    0.100356    0.162356    0.654126    11.00000    0.03018    0.03630 = 
         0.03669   -0.00483    0.00647    0.00381 
AFIX  43 
H4    2    0.099452    0.273159    0.653504    11.00000   -1.20000 
AFIX   0 
C5    1    0.073101    0.081316    0.788562    11.00000    0.03475    0.04824 = 
         0.03401   -0.00868    0.01093   -0.00008 
AFIX  43 
H5    2    0.054491    0.136746    0.880360    11.00000   -1.20000 
AFIX   0 
C6    1    0.409202    0.000000    0.943725    10.50000    0.01865    0.01946 = 
         0.03308    0.00000    0.00615    0.00000 
C7    1    0.427994    0.000000    1.105654    10.50000    0.02187    0.02308 = 
         0.02803    0.00000    0.01200    0.00000 
AFIX  43 
H7    2    0.377546    0.000000    1.177263    10.50000   -1.20000 
AFIX   0 
C8    1    0.518236    0.000000    1.163223    10.50000    0.03100    0.03049 = 
         0.02852    0.00000    0.00724    0.00000 
AFIX  43 
H8    2    0.531622    0.000000    1.274851    10.50000   -1.20000 
AFIX   0 
N1    3    0.311633    0.000000    0.884261    10.50000    0.02306    0.03213 = 
         0.03389    0.00000    0.00763    0.00000 
AFIX 137 
PART  -1 
H1A   2    0.292300   -0.099945    0.866941    10.50000   -1.20000 
H1B   2    0.307136    0.054434    0.791249    10.50000   -1.20000 
H1C   2    0.274554    0.045511    0.957473    10.50000   -1.20000 
AFIX   0 
PART   0 
O1    4    0.161237    0.311739    0.380632    11.00000    0.04625    0.02096 = 
         0.04342    0.00195    0.00758    0.00476 
PART 2 
O2    4    0.213938    0.164150    0.116444    10.50000    0.02972    0.02741 = 
         0.03541    0.00168    0.00980    0.00035 
PART 0 
  
HKLF 4 
  
REM  1 in C2/m 
REM R1 =  0.0982 for     737 Fo > 4sig(Fo)  and  0.1261 for all     985 data 
REM     90 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0735     10.1784 
  
REM Highest difference peak  0.404,  deepest hole -0.558,  1-sigma level  0.099 
Q1    1   0.0551  0.0000  0.7468  10.50000  0.05    0.40 
;
_shelx_res_checksum              92119
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1892(3) 0.0807(6) 0.2372(6) 0.0288(12) Uani 1 1 d . . . . .
H1 H 0.2084 0.1355 0.1453 0.035 Uiso 0.5 1 calc R U P A 1
C2 C 0.1600(3) 0.1685(6) 0.3777(6) 0.0301(12) Uani 1 1 d . . . . .
C3 C 0.1288(3) 0.0815(6) 0.5210(6) 0.0276(12) Uani 1 1 d . . . . .
C4 C 0.1004(3) 0.1624(7) 0.6541(6) 0.0343(13) Uani 1 1 d . . . . .
H4 H 0.0995 0.2732 0.6535 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0731(4) 0.0813(7) 0.7886(6) 0.0388(14) Uani 1 1 d . . . . .
H5 H 0.0545 0.1367 0.8804 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4092(4) 0.0000 0.9437(8) 0.0236(16) Uani 1 2 d S T P . .
C7 C 0.4280(5) 0.0000 1.1057(8) 0.0241(16) Uani 1 2 d S T P . .
H7 H 0.3775 0.0000 1.1773 0.029 Uiso 1 2 calc R U P . .
C8 C 0.5182(5) 0.0000 1.1632(9) 0.0299(17) Uani 1 2 d S T P . .
H8 H 0.5316 0.0000 1.2749 0.036 Uiso 1 2 calc R U P . .
N1 N 0.3116(4) 0.0000 0.8843(7) 0.0295(15) Uani 1 2 d S T P . .
H1A H 0.2923 -0.0999 0.8669 0.035 Uiso 0.5 1 calc R U P B -1
H1B H 0.3071 0.0544 0.7912 0.035 Uiso 0.5 1 calc R U P B -1
H1C H 0.2746 0.0455 0.9575 0.035 Uiso 0.5 1 calc R U P B -1
O1 O 0.1612(3) 0.3117(4) 0.3806(4) 0.0367(11) Uani 1 1 d . . . . .
O2 O 0.2139(5) 0.1641(8) 0.1164(8) 0.0307(17) Uani 0.5 1 d . . P C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.019(2) 0.036(3) 0.032(3) 0.002(2) 0.0050(19) -0.002(2)
C2 0.025(2) 0.028(3) 0.038(3) 0.006(2) 0.001(2) 0.002(2)
C3 0.017(2) 0.034(3) 0.032(3) -0.003(2) 0.0051(19) 0.003(2)
C4 0.030(3) 0.036(3) 0.037(3) -0.005(2) 0.006(2) 0.004(2)
C5 0.035(3) 0.048(3) 0.034(3) -0.009(3) 0.011(2) 0.000(3)
C6 0.019(3) 0.019(3) 0.033(4) 0.000 0.006(3) 0.000
C7 0.022(4) 0.023(4) 0.028(4) 0.000 0.012(3) 0.000
C8 0.031(4) 0.030(4) 0.029(4) 0.000 0.007(3) 0.000
N1 0.023(3) 0.032(3) 0.034(4) 0.000 0.008(3) 0.000
O1 0.046(2) 0.021(2) 0.043(2) 0.0019(17) 0.0076(17) 0.0048(18)
O2 0.030(4) 0.027(4) 0.035(4) 0.002(3) 0.010(3) 0.000(3)
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
O2 C1 C1 123.4(4) . 6
O2 C1 C2 115.8(5) . .
C1 C1 C2 120.8(3) 6 .
C1 C1 H1 119.6 6 .
C2 C1 H1 119.6 . .
O1 C2 C1 121.6(5) . .
O1 C2 C3 119.1(5) . .
C1 C2 C3 119.3(4) . .
C4 C3 C3 120.0(3) . 6
C4 C3 C2 120.1(5) . .
C3 C3 C2 119.9(3) 6 .
C3 C4 C5 120.0(5) . .
C3 C4 H4 120.0 . .
C5 C4 H4 120.0 . .
C4 C5 C5 120.0(3) . 6
C4 C5 H5 120.0 . .
C5 C5 H5 120.0 6 .
C7 C6 C8 120.9(6) . 5_657
C7 C6 N1 119.3(6) . .
C8 C6 N1 119.7(6) 5_657 .
C8 C7 C6 120.2(6) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C8 C6 118.9(7) . 5_657
C7 C8 H8 120.6 . .
C6 C8 H8 120.6 5_657 .
C6 N1 H1A 109.5 . .
C6 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C6 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.298(8) .
C1 C1 1.384(11) 6
C1 C2 1.469(7) .
C1 H1 0.9500 .
C2 O1 1.229(6) .
C2 C3 1.495(7) .
C3 C4 1.386(7) .
C3 C3 1.397(11) 6
C4 C5 1.391(7) .
C4 H4 0.9500 .
C5 C5 1.394(12) 6
C5 H5 0.9500 .
C6 C7 1.377(10) .
C6 C8 1.388(9) 5_657
C6 N1 1.458(9) .
C7 C8 1.355(10) .
C7 H7 0.9500 .
C8 C6 1.388(9) 5_657
C8 H8 0.9500 .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N1 H1C 0.9100 .
