#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:36:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180087 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/33/7053337.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_7053337
loop_
_publ_author_name
'Clausen, Henrik F.'
'Chevallier, Marie S.'
'Spackman, Mark A.'
'Iversen, Bo B.'
_publ_section_title
;
 Three new co-crystals of hydroquinone: crystal structures and Hirshfeld
 surface analysis of intermolecular interactions
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              193
_journal_paper_doi               10.1039/b9nj00463g
_journal_volume                  34
_journal_year                    2010
_chemical_formula_moiety         'C5 H11 N O, 2.5(C6 H6 O2)'
_chemical_formula_sum            'C20 H26 N O6'
_chemical_formula_weight         376.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.171(1)
_cell_angle_beta                 92.245(2)
_cell_angle_gamma                99.443(2)
_cell_formula_units_Z            2
_cell_length_a                   5.5742(1)
_cell_length_b                   9.8776(3)
_cell_length_c                   17.6573(4)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.698
_cell_measurement_theta_min      2.358
_cell_volume                     938.33(4)
_computing_cell_refinement       'Saint+ (Bruker, 2004)'
_computing_data_collection       'ApexII (Bruker, 2004)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics
;
XShell (Bruker, 2000) and Crystal Explorer (Wolff et al., 2005)
;
_computing_publication_material
;
enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28368
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.896540
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
'SADABS; Sheldrick, 1996.'
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         7063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.2105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                5086
_reflns_number_total             7063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b9nj00463g.txt
_cod_data_source_block           hq_def_abs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               7053337
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.31711(17) -0.05779(9) 0.26014(5) 0.01858(19) Uani 1 1 d .
H1 H 0.3289 -0.1250 0.2240 0.028 Uiso 1 1 calc R
C1 C 0.5087(2) 0.05105(12) 0.26095(6) 0.0146(2) Uani 1 1 d .
C2 C 0.6900(2) 0.04178(12) 0.20929(7) 0.0164(2) Uani 1 1 d .
H2 H 0.6829 -0.0407 0.1707 0.020 Uiso 1 1 calc R
C3 C 0.8810(2) 0.15285(13) 0.21414(7) 0.0175(2) Uani 1 1 d .
H3 H 1.0047 0.1464 0.1787 0.021 Uiso 1 1 calc R
C4 C 0.8928(2) 0.27398(12) 0.27066(7) 0.0162(2) Uani 1 1 d .
C5 C 0.7100(2) 0.28347(12) 0.32177(7) 0.0163(2) Uani 1 1 d .
H5 H 0.7166 0.3661 0.3602 0.020 Uiso 1 1 calc R
C6 C 0.5180(2) 0.17251(12) 0.31677(7) 0.0160(2) Uani 1 1 d .
H6 H 0.3927 0.1796 0.3516 0.019 Uiso 1 1 calc R
O4 O 1.08455(17) 0.38070(9) 0.27173(5) 0.0217(2) Uani 1 1 d .
H4 H 1.0915 0.4403 0.3131 0.033 Uiso 1 1 calc R
O11 O 0.17756(16) 0.58584(9) 0.40370(5) 0.01778(18) Uani 1 1 d .
H11 H 0.2235 0.6701 0.4011 0.027 Uiso 1 1 calc R
C11 C 0.3416(2) 0.54627(12) 0.45223(6) 0.0149(2) Uani 1 1 d .
C12 C 0.2749(2) 0.41806(12) 0.47328(7) 0.0166(2) Uani 1 1 d .
H12 H 0.1207 0.3621 0.4549 0.020 Uiso 1 1 calc R
C13 C 0.4329(2) 0.37087(12) 0.52120(7) 0.0158(2) Uani 1 1 d .
H13 H 0.3872 0.2829 0.5356 0.019 Uiso 1 1 calc R
O21 O 0.28021(16) 0.86069(9) 0.39612(5) 0.01753(19) Uani 1 1 d .
H21 H 0.2765 0.8880 0.3540 0.026 Uiso 1 1 calc R
C21 C 0.1397(2) 0.93271(12) 0.44678(6) 0.0141(2) Uani 1 1 d .
C22 C -0.0225(2) 1.01138(12) 0.42267(7) 0.0160(2) Uani 1 1 d .
H22 H -0.0378 1.0191 0.3700 0.019 Uiso 1 1 calc R
C23 C -0.1619(2) 1.07867(12) 0.47645(7) 0.0165(2) Uani 1 1 d .
H23 H -0.2730 1.1328 0.4604 0.020 Uiso 1 1 calc R
O31 O 0.87579(17) 0.76270(9) 1.06161(5) 0.0211(2) Uani 1 1 d .
H31 H 0.9958 0.7489 1.0875 0.032 Uiso 1 1 calc R
C31 C 0.9419(2) 0.88082(12) 1.03167(7) 0.0155(2) Uani 1 1 d .
C32 C 0.7662(2) 0.92274(12) 0.98790(7) 0.0163(2) Uani 1 1 d .
H32 H 0.6053 0.8702 0.9797 0.020 Uiso 1 1 calc R
C33 C 0.8236(2) 1.04077(12) 0.95607(7) 0.0166(2) Uani 1 1 d .
H33 H 0.7025 1.0682 0.9258 0.020 Uiso 1 1 calc R
O41 O 0.28385(17) 0.72175(9) 0.14297(5) 0.01966(19) Uani 1 1 d .
C41 C 0.3489(2) 0.60671(13) 0.12018(7) 0.0173(2) Uani 1 1 d .
H41 H 0.3098 0.5638 0.0672 0.021 Uiso 1 1 calc R
N41 N 0.46627(19) 0.53912(10) 0.16242(6) 0.0161(2) Uani 1 1 d .
C42 C 0.5336(2) 0.59636(13) 0.24500(7) 0.0177(2) Uani 1 1 d .
H42A H 0.5338 0.5176 0.2721 0.021 Uiso 1 1 calc R
H42B H 0.4078 0.6498 0.2666 0.021 Uiso 1 1 calc R
C43 C 0.5193(2) 0.40064(13) 0.12701(8) 0.0222(3) Uani 1 1 d .
H43A H 0.4051 0.3603 0.0808 0.027 Uiso 1 1 calc R
H43B H 0.4903 0.3377 0.1643 0.027 Uiso 1 1 calc R
C44 C 0.7807(3) 0.69134(14) 0.26141(8) 0.0227(3) Uani 1 1 d .
H44A H 0.9081 0.6375 0.2439 0.034 Uiso 1 1 calc R
H44B H 0.8098 0.7293 0.3172 0.034 Uiso 1 1 calc R
H44C H 0.7839 0.7686 0.2338 0.034 Uiso 1 1 calc R
C45 C 0.7789(2) 0.40531(14) 0.10321(7) 0.0222(3) Uani 1 1 d .
H45A H 0.8150 0.4750 0.0707 0.033 Uiso 1 1 calc R
H45B H 0.7968 0.3129 0.0740 0.033 Uiso 1 1 calc R
H45C H 0.8924 0.4310 0.1495 0.033 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
C1 O1 H1 109.5 . .
O1 C1 C6 117.60(11) . .
O1 C1 C2 122.52(10) . .
C6 C1 C2 119.88(11) . .
C3 C2 C1 119.97(11) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C2 C3 C4 120.33(11) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
O4 C4 C5 122.94(11) . .
O4 C4 C3 117.47(11) . .
C5 C4 C3 119.57(12) . .
C6 C5 C4 120.16(11) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 120.08(11) . .
C5 C6 H6 120.0 . .
C1 C6 H6 120.0 . .
C4 O4 H4 109.5 . .
C11 O11 H11 109.5 . .
O11 C11 C12 117.29(11) . .
O11 C11 C13 122.37(11) . 2_666
C12 C11 C13 120.33(11) . 2_666
C11 C12 C13 120.29(12) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C13 C11 119.38(11) . 2_666
C12 C13 H13 120.3 . .
C11 C13 H13 120.3 2_666 .
C21 O21 H21 109.5 . .
O21 C21 C23 117.26(10) . 2_576
O21 C21 C22 122.36(10) . .
C23 C21 C22 120.36(11) 2_576 .
C21 C22 C23 119.31(11) . .
C21 C22 H22 120.3 . .
C23 C22 H22 120.3 . .
C21 C23 C22 120.33(11) 2_576 .
C21 C23 H23 119.8 2_576 .
C22 C23 H23 119.8 . .
C31 O31 H31 109.5 . .
O31 C31 C32 118.19(11) . .
O31 C31 C33 122.53(11) . 2_777
C32 C31 C33 119.28(11) . 2_777
C33 C32 C31 120.51(12) . .
C33 C32 H32 119.7 . .
C31 C32 H32 119.7 . .
C32 C33 C31 120.21(11) . 2_777
C32 C33 H33 119.9 . .
C31 C33 H33 119.9 2_777 .
O41 C41 N41 126.26(11) . .
O41 C41 H41 116.9 . .
N41 C41 H41 116.9 . .
C41 N41 C42 121.01(10) . .
C41 N41 C43 119.21(10) . .
C42 N41 C43 119.70(10) . .
N41 C42 C44 113.96(11) . .
N41 C42 H42A 108.8 . .
C44 C42 H42A 108.8 . .
N41 C42 H42B 108.8 . .
C44 C42 H42B 108.8 . .
H42A C42 H42B 107.7 . .
N41 C43 C45 113.32(11) . .
N41 C43 H43A 108.9 . .
C45 C43 H43A 108.9 . .
N41 C43 H43B 108.9 . .
C45 C43 H43B 108.9 . .
H43A C43 H43B 107.7 . .
C42 C44 H44A 109.5 . .
C42 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
C42 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
C43 C45 H45A 109.5 . .
C43 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
C43 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3829(16) .
O1 H1 0.8400 .
C1 C6 1.3896(16) .
C1 C2 1.3901(17) .
C2 C3 1.3849(18) .
C2 H2 0.9500 .
C3 C4 1.3921(16) .
C3 H3 0.9500 .
C4 O4 1.3691(16) .
C4 C5 1.3902(18) .
C5 C6 1.3874(18) .
C5 H5 0.9500 .
C6 H6 0.9500 .
O4 H4 0.8400 .
O11 C11 1.3816(15) .
O11 H11 0.8400 .
C11 C12 1.3851(17) .
C11 C13 1.3922(18) 2_666
C12 C13 1.3921(17) .
C12 H12 0.9500 .
C13 H13 0.9500 .
O21 C21 1.3824(14) .
O21 H21 0.8400 .
C21 C23 1.3843(16) 2_576
C21 C22 1.3893(17) .
C22 C23 1.3894(17) .
C22 H22 0.9500 .
C23 H23 0.9500 .
O31 C31 1.3747(15) .
O31 H31 0.8400 .
C31 C32 1.3878(17) .
C31 C33 1.3912(18) 2_777
C32 C33 1.3867(18) .
C32 H32 0.9500 .
C33 H33 0.9500 .
O41 C41 1.2465(14) .
C41 N41 1.3147(16) .
C41 H41 0.9500 .
N41 C42 1.4679(16) .
N41 C43 1.4715(15) .
C42 C44 1.5172(19) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C45 1.5185(19) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
