#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/02/2100235.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2100235
loop_
_publ_author_name
'Oswald, Iain D. H.'
'Motherwell, W. D. Samuel'
'Parsons, Simon'
_publ_section_title
;
 Formation of quinol co-crystals with hydrogen-bond acceptors
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              46
_journal_page_last               57
_journal_paper_doi               10.1107/S0108768104028605
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         C6H14N2.C6H6O2
_chemical_formula_sum            'C12 H20 N2 O2'
_chemical_formula_weight         224.30
_chemical_name_common            Quinol:dimethylpiperazine
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                90.501(2)
_cell_angle_beta                 92.919(2)
_cell_angle_gamma                99.664(2)
_cell_formula_units_Z            4
_cell_length_a                   8.9620(8)
_cell_length_b                   9.4944(8)
_cell_length_c                   14.7119(13)
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.6
_cell_volume                     1232.26(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11345
_diffrn_reflns_theta_full        28.93
_diffrn_reflns_theta_max         28.93
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0743
_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)+(0.0536P)²+0.5870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                3873
_reflns_number_total             5844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ws5013.cif
_cod_data_source_block           8
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2100235
_cod_database_fobs_code          2100235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1A 0.1999(2) 0.55595(18) 0.10784(12) 0.0303(4) Uani d . 1 . . O
C1A 0.1227(2) 0.4712(2) 0.17097(15) 0.0225(5) Uani d . 1 . . C
C2A 0.1675(3) 0.3471(2) 0.20331(15) 0.0228(5) Uani d . 1 . . C
H2A 0.2568 0.3187 0.1825 0.027 Uiso calc R 1 . . H
C3A 0.0827(3) 0.2642(2) 0.26600(15) 0.0240(5) Uani d . 1 . . C
H3A 0.1149 0.1797 0.2878 0.029 Uiso calc R 1 . . H
C4A -0.0481(3) 0.3030(2) 0.29706(15) 0.0239(5) Uani d . 1 . . C
O4A -0.13639(19) 0.22739(19) 0.35842(12) 0.0321(4) Uani d . 1 . . O
C5A -0.0917(3) 0.4278(3) 0.26438(17) 0.0287(6) Uani d . 1 . . C
H5A -0.1809 0.4565 0.2851 0.034 Uiso calc R 1 . . H
C6A -0.0074(3) 0.5104(3) 0.20244(17) 0.0294(6) Uani d . 1 . . C
H6A -0.0392 0.5954 0.1811 0.035 Uiso calc R 1 . . H
O1B 0.3462(2) 0.08746(19) 0.11340(12) 0.0335(4) Uani d . 1 . . O
C1B 0.3689(3) 0.0181(2) 0.19305(15) 0.0240(5) Uani d . 1 . . C
C2B 0.3072(3) -0.1238(2) 0.20638(16) 0.0247(5) Uani d . 1 . . C
H2B 0.2451 -0.1766 0.1593 0.030 Uiso calc R 1 . . H
C3B 0.3356(3) -0.1891(2) 0.28792(15) 0.0238(5) Uani d . 1 . . C
H3B 0.2924 -0.2862 0.2964 0.029 Uiso calc R 1 . . H
C4B 0.4263(3) -0.1139(2) 0.35694(15) 0.0218(5) Uani d . 1 . . C
O4B 0.4586(2) -0.17203(19) 0.43913(11) 0.0320(4) Uani d . 1 . . O
C5B 0.4880(3) 0.0278(3) 0.34385(16) 0.0290(6) Uani d . 1 . . C
H5B 0.5499 0.0808 0.3910 0.035 Uiso calc R 1 . . H
C6B 0.4598(3) 0.0924(3) 0.26233(16) 0.0302(6) Uani d . 1 . . C
H6B 0.5035 0.1894 0.2538 0.036 Uiso calc R 1 . . H
C1S 0.8070(3) 0.4747(3) 0.53140(17) 0.0293(6) Uani d . 1 . . C
H1S1 0.8413 0.3991 0.4963 0.044 Uiso calc R 1 . . H
H1S2 0.8430 0.4710 0.5952 0.044 Uiso calc R 1 . . H
H1S3 0.8476 0.5680 0.5067 0.044 Uiso calc R 1 . . H
N1S 0.6414(2) 0.4539(2) 0.52553(13) 0.0216(4) Uani d . 1 . . N
C2S 0.5855(3) 0.5654(2) 0.57718(15) 0.0235(5) Uani d . 1 . . C
H2S1 0.6272 0.6604 0.5534 0.028 Uiso calc R 1 . . H
H2S2 0.6206 0.5628 0.6419 0.028 Uiso calc R 1 . . H
C3S 0.4148(3) 0.5441(2) 0.56985(15) 0.0221(5) Uani d . 1 . . C
H3S1 0.3731 0.4514 0.5967 0.027 Uiso calc R 1 . . H
H3S2 0.3795 0.6208 0.6047 0.027 Uiso calc R 1 . . H
C1T 0.5811(3) 0.6117(3) 0.17652(17) 0.0365(6) Uani d . 1 . . C
H1T1 0.5542 0.5472 0.2270 0.055 Uiso calc R 1 . . H
H1T2 0.5517 0.7044 0.1893 0.055 Uiso calc R 1 . . H
H1T3 0.6907 0.6245 0.1696 0.055 Uiso calc R 1 . . H
N1T 0.5015(2) 0.5503(2) 0.09256(13) 0.0265(5) Uani d . 1 . . N
C2T 0.5346(3) 0.6488(3) 0.01698(16) 0.0282(5) Uani d . 1 . . C
H2T1 0.6451 0.6670 0.0087 0.034 Uiso calc R 1 . . H
H2T2 0.5029 0.7411 0.0313 0.034 Uiso calc R 1 . . H
C3T 0.4516(3) 0.5856(3) -0.06968(16) 0.0281(6) Uani d . 1 . . C
H3T1 0.3410 0.5700 -0.0619 0.034 Uiso calc R 1 . . H
H3T2 0.4737 0.6532 -0.1200 0.034 Uiso calc R 1 . . H
C1U 0.8613(4) 0.8646(3) 0.33895(19) 0.0454(7) Uani d . 1 . . C
H1U1 0.8664 0.7672 0.3589 0.068 Uiso calc R 1 . . H
H1U2 0.9173 0.8838 0.2837 0.068 Uiso calc R 1 . . H
H1U3 0.7551 0.8744 0.3262 0.068 Uiso calc R 1 . . H
N1U 0.9284(2) 0.9667(2) 0.41090(13) 0.0259(5) Uani d . 1 . . N
C2U 0.8448(3) 0.9402(3) 0.49425(17) 0.0285(6) Uani d . 1 . . C
H2U1 0.8481 0.8416 0.5147 0.034 Uiso calc R 1 . . H
H2U2 0.7374 0.9492 0.4812 0.034 Uiso calc R 1 . . H
C3U 0.9125(3) 1.0445(3) 0.56829(16) 0.0282(6) Uani d . 1 . . C
H3U1 0.9053 1.1428 0.5488 0.034 Uiso calc R 1 . . H
H3U2 0.8547 1.0251 0.6237 0.034 Uiso calc R 1 . . H
C1V 0.2262(4) -0.1396(5) -0.0664(3) 0.0975(18) Uani d . 1 . . C
H1V4 0.2578 -0.2131 -0.0269 0.146 Uiso calc R 1 . . H
H1V5 0.3161 -0.0779 -0.0876 0.146 Uiso calc R 1 . . H
H1V6 0.1647 -0.1855 -0.1189 0.146 Uiso calc R 1 . . H
N1V 0.1361(2) -0.0532(3) -0.01501(14) 0.0364(6) Uani d . 1 . . N
C2V 0.0881(3) 0.0589(3) -0.06965(17) 0.0420(7) Uani d . 1 . . C
H2V1 0.0257 0.0160 -0.1236 0.050 Uiso calc R 1 . . H
H2V2 0.1781 0.1221 -0.0913 0.050 Uiso calc R 1 . . H
C3V -0.0015(3) 0.1443(3) -0.0158(2) 0.0429(8) Uani d . 1 . . C
H3V1 0.0614 0.1890 0.0375 0.051 Uiso calc R 1 . . H
H3V2 -0.0319 0.2215 -0.0537 0.051 Uiso calc R 1 . . H
H4B 0.422(4) -0.269(3) 0.439(2) 0.058(10) Uiso d . 1 . . H
H1A 0.295(4) 0.541(3) 0.106(2) 0.054(9) Uiso d . 1 . . H
H4A -0.101(4) 0.138(3) 0.371(2) 0.062(10) Uiso d . 1 . . H
H1B 0.273(4) 0.030(3) 0.074(2) 0.068(11) Uiso d . 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1A O1A H1A . . 111.1(19)
O1A C1A C6A . . 118.1(2)
O1A C1A C2A . . 123.2(2)
C6A C1A C2A . . 118.7(2)
C1A C2A C3A . . 120.4(2)
C1A C2A H2A . . 119.8
C3A C2A H2A . . 119.8
C4A C3A C2A . . 120.9(2)
C4A C3A H3A . . 119.6
C2A C3A H3A . . 119.6
O4A C4A C3A . . 124.1(2)
O4A C4A C5A . . 117.7(2)
C3A C4A C5A . . 118.2(2)
C4A O4A H4A . . 109.7(18)
C6A C5A C4A . . 121.0(2)
C6A C5A H5A . . 119.5
C4A C5A H5A . . 119.5
C5A C6A C1A . . 120.8(2)
C5A C6A H6A . . 119.6
C1A C6A H6A . . 119.6
C1B O1B H1B . . 110.4(19)
O1B C1B C6B . . 118.3(2)
O1B C1B C2B . . 123.0(2)
C6B C1B C2B . . 118.7(2)
C1B C2B C3B . . 120.5(2)
C1B C2B H2B . . 119.7
C3B C2B H2B . . 119.7
C4B C3B C2B . . 120.4(2)
C4B C3B H3B . . 119.8
C2B C3B H3B . . 119.8
O4B C4B C3B . . 123.4(2)
O4B C4B C5B . . 117.5(2)
C3B C4B C5B . . 119.2(2)
C4B O4B H4B . . 111.0(19)
C6B C5B C4B . . 120.2(2)
C6B C5B H5B . . 119.9
C4B C5B H5B . . 119.9
C1B C6B C5B . . 121.0(2)
C1B C6B H6B . . 119.5
C5B C6B H6B . . 119.5
N1S C1S H1S1 . . 109.5
N1S C1S H1S2 . . 109.5
H1S1 C1S H1S2 . . 109.5
N1S C1S H1S3 . . 109.5
H1S1 C1S H1S3 . . 109.5
H1S2 C1S H1S3 . . 109.5
C1S N1S C2S . . 111.13(17)
C1S N1S C3S . 2_666 110.22(18)
C2S N1S C3S . 2_666 109.13(17)
N1S C2S C3S . . 110.75(18)
N1S C2S H2S1 . . 109.5
C3S C2S H2S1 . . 109.5
N1S C2S H2S2 . . 109.5
C3S C2S H2S2 . . 109.5
H2S1 C2S H2S2 . . 108.1
N1S C3S C2S 2_666 . 110.94(18)
N1S C3S H3S1 2_666 . 109.5
C2S C3S H3S1 . . 109.5
N1S C3S H3S2 2_666 . 109.5
C2S C3S H3S2 . . 109.5
H3S1 C3S H3S2 . . 108.0
N1T C1T H1T1 . . 109.5
N1T C1T H1T2 . . 109.5
H1T1 C1T H1T2 . . 109.5
N1T C1T H1T3 . . 109.5
H1T1 C1T H1T3 . . 109.5
H1T2 C1T H1T3 . . 109.5
C1T N1T C3T . 2_665 110.62(19)
C1T N1T C2T . . 110.2(2)
C3T N1T C2T 2_665 . 108.72(18)
N1T C2T C3T . . 110.19(19)
N1T C2T H2T1 . . 109.6
C3T C2T H2T1 . . 109.6
N1T C2T H2T2 . . 109.6
C3T C2T H2T2 . . 109.6
H2T1 C2T H2T2 . . 108.1
N1T C3T C2T 2_665 . 110.37(19)
N1T C3T H3T1 2_665 . 109.6
C2T C3T H3T1 . . 109.6
N1T C3T H3T2 2_665 . 109.6
C2T C3T H3T2 . . 109.6
H3T1 C3T H3T2 . . 108.1
N1U C1U H1U1 . . 109.5
N1U C1U H1U2 . . 109.5
H1U1 C1U H1U2 . . 109.5
N1U C1U H1U3 . . 109.5
H1U1 C1U H1U3 . . 109.5
H1U2 C1U H1U3 . . 109.5
C1U N1U C3U . 2_776 111.1(2)
C1U N1U C2U . . 110.2(2)
C3U N1U C2U 2_776 . 108.81(18)
N1U C2U C3U . . 110.66(19)
N1U C2U H2U1 . . 109.5
C3U C2U H2U1 . . 109.5
N1U C2U H2U2 . . 109.5
C3U C2U H2U2 . . 109.5
H2U1 C2U H2U2 . . 108.1
N1U C3U C2U 2_776 . 110.72(19)
N1U C3U H3U1 2_776 . 109.5
C2U C3U H3U1 . . 109.5
N1U C3U H3U2 2_776 . 109.5
C2U C3U H3U2 . . 109.5
H3U1 C3U H3U2 . . 108.1
N1V C1V H1V4 . . 109.5
N1V C1V H1V5 . . 109.5
H1V4 C1V H1V5 . . 109.5
N1V C1V H1V6 . . 109.5
H1V4 C1V H1V6 . . 109.5
H1V5 C1V H1V6 . . 109.5
C2V N1V C3V . 2 108.3(2)
C2V N1V C1V . . 112.0(3)
C3V N1V C1V 2 . 109.7(3)
N1V C2V C3V . . 110.6(2)
N1V C2V H2V1 . . 109.5
C3V C2V H2V1 . . 109.5
N1V C2V H2V2 . . 109.5
C3V C2V H2V2 . . 109.5
H2V1 C2V H2V2 . . 108.1
N1V C3V C2V 2 . 110.1(2)
N1V C3V H3V1 2 . 109.6
C2V C3V H3V1 . . 109.6
N1V C3V H3V2 2 . 109.6
C2V C3V H3V2 . . 109.6
H3V1 C3V H3V2 . . 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C1A . 1.371(3) ?
O1A H1A . 0.89(3) ?
C1A C6A . 1.382(3) ?
C1A C2A . 1.387(3) ?
C2A C3A . 1.390(3) ?
C2A H2A . 0.9500 ?
C3A C4A . 1.384(3) ?
C3A H3A . 0.9500 ?
C4A O4A . 1.360(3) ?
C4A C5A . 1.390(3) ?
O4A H4A . 0.97(3) ?
C5A C6A . 1.379(3) ?
C5A H5A . 0.9500 ?
C6A H6A . 0.9500 ?
O1B C1B . 1.372(3) ?
O1B H1B . 0.95(3) ?
C1B C6B . 1.382(3) ?
C1B C2B . 1.387(3) ?
C2B C3B . 1.387(3) ?
C2B H2B . 0.9500 ?
C3B C4B . 1.382(3) ?
C3B H3B . 0.9500 ?
C4B O4B . 1.371(3) ?
C4B C5B . 1.386(3) ?
O4B H4B . 0.92(3) ?
C5B C6B . 1.383(3) ?
C5B H5B . 0.9500 ?
C6B H6B . 0.9500 ?
C1S N1S . 1.462(3) ?
C1S H1S1 . 0.9800 ?
C1S H1S2 . 0.9800 ?
C1S H1S3 . 0.9800 ?
N1S C2S . 1.467(3) ?
N1S C3S 2_666 1.468(3) ?
C2S C3S . 1.507(3) ?
C2S H2S1 . 0.9900 ?
C2S H2S2 . 0.9900 ?
C3S N1S 2_666 1.468(3) ?
C3S H3S1 . 0.9900 ?
C3S H3S2 . 0.9900 ?
C1T N1T . 1.460(3) ?
C1T H1T1 . 0.9800 ?
C1T H1T2 . 0.9800 ?
C1T H1T3 . 0.9800 ?
N1T C3T 2_665 1.465(3) ?
N1T C2T . 1.468(3) ?
C2T C3T . 1.509(3) ?
C2T H2T1 . 0.9900 ?
C2T H2T2 . 0.9900 ?
C3T N1T 2_665 1.465(3) ?
C3T H3T1 . 0.9900 ?
C3T H3T2 . 0.9900 ?
C1U N1U . 1.464(3) ?
C1U H1U1 . 0.9800 ?
C1U H1U2 . 0.9800 ?
C1U H1U3 . 0.9800 ?
N1U C3U 2_776 1.465(3) ?
N1U C2U . 1.471(3) ?
C2U C3U . 1.499(3) ?
C2U H2U1 . 0.9900 ?
C2U H2U2 . 0.9900 ?
C3U N1U 2_776 1.465(3) ?
C3U H3U1 . 0.9900 ?
C3U H3U2 . 0.9900 ?
C1V N1V . 1.474(4) ?
C1V H1V4 . 0.9800 ?
C1V H1V5 . 0.9800 ?
C1V H1V6 . 0.9800 ?
N1V C2V . 1.448(3) ?
N1V C3V 2 1.457(4) ?
C2V C3V . 1.484(4) ?
C2V H2V1 . 0.9900 ?
C2V H2V2 . 0.9900 ?
C3V N1V 2 1.457(4) ?
C3V H3V1 . 0.9900 ?
C3V H3V2 . 0.9900 ?
