#------------------------------------------------------------------------------
#$Date: 2016-03-13 15:25:55 +0200 (Sun, 13 Mar 2016) $
#$Revision: 178180 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/28/1542805.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_1542805
loop_
_publ_author_name
'Dubey, Ritesh'
'Desiraju, Gautam R.'
_publ_section_title
;
 Combinatorial selection of molecular conformations and supramolecular
 synthons in quercetin cocrystal landscapes: a route to ternary solids
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first              402
_journal_page_last               408
_journal_paper_doi               10.1107/S2052252515009884
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C33 H22 N3 O8'
_chemical_formula_weight         588.53
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                104.785(4)
_cell_angle_beta                 108.855(4)
_cell_angle_gamma                90.687(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4800(7)
_cell_length_b                   11.2614(9)
_cell_length_c                   13.5129(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1312.95(18)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14918
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.656
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Bruker, AXS, 2008'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       Plate
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0602P)²+0.3828P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3747
_reflns_number_total             5100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lc5063.cif
_cod_data_source_block           QPH_IV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/usr/data/users/saulius/automatic-downloads/current/IUCr/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 4287 2015-11-16 14:04:37Z antanas 
;
_cod_original_cell_volume        1312.94(18)
_cod_database_code               1542805
_publcif_datablock.id            {2b0a1fac-39b9-48e5-84aa-0bc1c73f01d0}
_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.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C6 C 1.12658(18) 0.61921(16) 0.48970(13) 0.0177(4) Uani 1 1 d . .
C9 C 1.01319(19) 0.83645(16) 0.56939(13) 0.0181(4) Uani 1 1 d . .
C10 C 0.93537(19) 0.94619(16) 0.59240(13) 0.0185(4) Uani 1 1 d . .
C2 C 0.89885(19) 0.57290(16) 0.33188(14) 0.0214(4) Uani 1 1 d . .
H2 H 0.8070 0.5950 0.2938 0.026 Uiso 1 1 calc R U
C7 C 1.21259(19) 0.70128(16) 0.59202(14) 0.0196(4) Uani 1 1 d . .
C11 C 0.99584(19) 1.04189(16) 0.68797(14) 0.0196(4) Uani 1 1 d . .
H11 H 1.0879 1.0357 0.7378 0.024 Uiso 1 1 calc R U
C4 C 1.08883(19) 0.42917(16) 0.34736(14) 0.0205(4) Uani 1 1 d . .
H4 H 1.1216 0.3549 0.3187 0.025 Uiso 1 1 calc R U
C1 C 0.98810(18) 0.64865(15) 0.43089(13) 0.0175(4) Uani 1 1 d . .
C32 C 0.6338(2) 0.48932(16) -0.01607(14) 0.0227(4) Uani 1 1 d . .
C8 C 1.14629(19) 0.80879(16) 0.63174(13) 0.0194(4) Uani 1 1 d . .
C22 C 1.24935(19) 0.16223(16) 0.03853(14) 0.0220(4) Uani 1 1 d . .
C12 C 0.92299(19) 1.14465(16) 0.71025(14) 0.0201(4) Uani 1 1 d . .
C33 C 0.4927(2) 0.47876(16) 0.09240(14) 0.0222(4) Uani 1 1 d . .
C21 C 1.3834(2) 0.18053(16) -0.07152(14) 0.0225(4) Uani 1 1 d . .
C14 C 0.7239(2) 1.06147(17) 0.54122(14) 0.0238(4) Uani 1 1 d . .
H14 H 0.6319 1.0680 0.4916 0.029 Uiso 1 1 calc R U
C16 C 1.5176(2) 0.16347(16) 0.00829(14) 0.0219(4) Uani 1 1 d . .
C27 C 1.38315(19) 0.14434(16) 0.11809(14) 0.0206(4) Uani 1 1 d . .
C17 C 1.6548(2) 0.16442(17) -0.01300(16) 0.0287(4) Uani 1 1 d . .
H17 H 1.7428 0.1538 0.0385 0.034 Uiso 1 1 calc R U
C3 C 0.9506(2) 0.46257(16) 0.29093(14) 0.0212(4) Uani 1 1 d . .
C26 C 1.3738(2) 0.12335(17) 0.21515(15) 0.0263(4) Uani 1 1 d . .
H26 H 1.4598 0.1116 0.2678 0.032 Uiso 1 1 calc R U
C31 C 0.7700(2) 0.47732(18) -0.03871(16) 0.0299(5) Uani 1 1 d . .
H31 H 0.8538 0.4575 0.0108 0.036 Uiso 1 1 calc R U
C5 C 1.17556(19) 0.50616(16) 0.44483(14) 0.0200(4) Uani 1 1 d . .
C28 C 0.5210(2) 0.54122(18) -0.18832(15) 0.0286(4) Uani 1 1 d . .
H28 H 0.4400 0.5639 -0.2380 0.034 Uiso 1 1 calc R U
C13 C 0.7853(2) 1.15602(16) 0.63573(14) 0.0205(4) Uani 1 1 d . .
C23 C 1.1118(2) 0.15935(18) 0.05933(16) 0.0303(5) Uani 1 1 d . .
H23 H 1.0240 0.1717 0.0085 0.036 Uiso 1 1 calc R U
C20 C 1.3921(2) 0.19844(18) -0.17006(16) 0.0308(5) Uani 1 1 d . .
H20 H 1.3061 0.2106 -0.2226 0.037 Uiso 1 1 calc R U
C19 C 1.5248(2) 0.19782(19) -0.18770(17) 0.0344(5) Uani 1 1 d . .
H19 H 1.5290 0.2086 -0.2527 0.041 Uiso 1 1 calc R U
C15 C 0.7968(2) 0.95755(17) 0.51923(14) 0.0221(4) Uani 1 1 d . .
H15 H 0.7533 0.8949 0.4554 0.027 Uiso 1 1 calc R U
C24 C 1.1082(2) 0.13861(19) 0.15303(16) 0.0323(5) Uani 1 1 d . .
H24 H 1.0177 0.1363 0.1659 0.039 Uiso 1 1 calc R U
C25 C 1.2410(2) 0.12041(18) 0.23148(15) 0.0305(5) Uani 1 1 d . .
H25 H 1.2365 0.1062 0.2953 0.037 Uiso 1 1 calc R U
C18 C 1.6576(2) 0.18084(18) -0.10807(17) 0.0333(5) Uani 1 1 d . .
H18 H 1.7478 0.1810 -0.1215 0.040 Uiso 1 1 calc R U
C29 C 0.6520(2) 0.52737(19) -0.20756(16) 0.0323(5) Uani 1 1 d . .
H29 H 0.6595 0.5395 -0.2713 0.039 Uiso 1 1 calc R U
C30 C 0.7781(2) 0.4947(2) -0.13254(17) 0.0344(5) Uani 1 1 d . .
H30 H 0.8669 0.4852 -0.1477 0.041 Uiso 1 1 calc R U
N5 N 0.62433(16) 0.46832(14) 0.07534(11) 0.0231(3) Uani 1 1 d . .
N11 N 1.51600(16) 0.14627(13) 0.10304(12) 0.0222(3) Uani 1 1 d . .
N12 N 1.25137(16) 0.18162(14) -0.05501(12) 0.0233(3) Uani 1 1 d . .
O7 O 0.93564(12) 0.75612(11) 0.47017(9) 0.0196(3) Uani 1 1 d . .
O3 O 1.34208(13) 0.68253(12) 0.64651(10) 0.0263(3) Uani 1 1 d . .
O1 O 0.87145(15) 0.38163(12) 0.19564(10) 0.0301(3) Uani 1 1 d . .
O4 O 1.22341(15) 0.88546(12) 0.73073(11) 0.0297(3) Uani 1 1 d . .
O8 O 0.47995(18) 1.27143(15) 0.48651(13) 0.0503(4) Uani 1 1 d . .
O2 O 1.30965(14) 0.47435(13) 0.50006(11) 0.0293(3) Uani 1 1 d . .
O6 O 0.71816(15) 1.26000(12) 0.66039(11) 0.0273(3) Uani 1 1 d . .
O5 O 0.97912(15) 1.23836(12) 0.80397(11) 0.0289(3) Uani 1 1 d . .
H1O H 0.784(3) 0.415(2) 0.1621(19) 0.053(7) Uiso 1 1 d . .
H5O H 1.074(3) 1.224(2) 0.847(2) 0.067(8) Uiso 1 1 d . .
H4O H 1.297(3) 0.853(2) 0.765(2) 0.057(8) Uiso 1 1 d . .
H2O H 1.345(3) 0.537(2) 0.5569(19) 0.048(7) Uiso 1 1 d . .
H6O H 0.640(3) 1.258(3) 0.601(2) 0.075(9) Uiso 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
_geom_angle_site_symmetry_3
C1 C6 C5 117.72(15) . .
C1 C6 C7 119.79(15) . .
C5 C6 C7 122.49(15) . .
C8 C9 O7 119.82(15) . .
C8 C9 C10 128.55(16) . .
O7 C9 C10 111.63(14) . .
C15 C10 C11 117.96(16) . .
C15 C10 C9 120.54(15) . .
C11 C10 C9 121.50(15) . .
C1 C2 C3 117.80(16) . .
C1 C2 H2 121.1 . .
C3 C2 H2 121.1 . .
O3 C7 C6 122.63(16) . .
O3 C7 C8 120.30(15) . .
C6 C7 C8 117.06(15) . .
C12 C11 C10 121.75(16) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C5 C4 C3 119.64(16) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
O7 C1 C2 117.13(15) . .
O7 C1 C6 120.17(15) . .
C2 C1 C6 122.70(16) . .
N5 C32 C31 120.12(16) . .
N5 C32 C33 120.75(16) . 2_665
C31 C32 C33 119.11(17) . 2_665
O4 C8 C9 120.88(16) . .
O4 C8 C7 118.08(15) . .
C9 C8 C7 120.96(15) . .
N12 C22 C23 119.66(16) . .
N12 C22 C27 121.27(16) . .
C23 C22 C27 119.07(16) . .
O5 C12 C11 122.65(16) . .
O5 C12 C13 117.47(16) . .
C11 C12 C13 119.87(16) . .
N5 C33 C28 119.59(16) . 2_665
N5 C33 C32 121.24(16) . 2_665
C28 C33 C32 119.17(17) 2_665 2_665
N12 C21 C20 119.72(17) . .
N12 C21 C16 121.65(16) . .
C20 C21 C16 118.63(17) . .
C15 C14 C13 121.22(16) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
N11 C16 C17 119.58(17) . .
N11 C16 C21 121.14(16) . .
C17 C16 C21 119.28(17) . .
N11 C27 C26 119.59(16) . .
N11 C27 C22 121.72(16) . .
C26 C27 C22 118.69(16) . .
C18 C17 C16 120.08(18) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
O1 C3 C2 122.48(16) . .
O1 C3 C4 116.10(16) . .
C2 C3 C4 121.42(16) . .
C25 C26 C27 120.44(18) . .
C25 C26 H26 119.8 . .
C27 C26 H26 119.8 . .
C30 C31 C32 120.07(18) . .
C30 C31 H31 120.0 . .
C32 C31 H31 120.0 . .
O2 C5 C4 119.97(16) . .
O2 C5 C6 119.31(15) . .
C4 C5 C6 120.71(15) . .
C29 C28 C33 119.92(18) . 2_665
C29 C28 H28 120.0 . .
C33 C28 H28 120.0 2_665 .
O6 C13 C14 123.23(16) . .
O6 C13 C12 117.90(16) . .
C14 C13 C12 118.87(16) . .
C24 C23 C22 120.14(18) . .
C24 C23 H23 119.9 . .
C22 C23 H23 119.9 . .
C19 C20 C21 120.33(19) . .
C19 C20 H20 119.8 . .
C21 C20 H20 119.8 . .
C20 C19 C18 120.71(18) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C14 C15 C10 120.32(17) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
C23 C24 C25 120.61(18) . .
C23 C24 H24 119.7 . .
C25 C24 H24 119.7 . .
C26 C25 C24 121.05(18) . .
C26 C25 H25 119.5 . .
C24 C25 H25 119.5 . .
C17 C18 C19 120.97(18) . .
C17 C18 H18 119.5 . .
C19 C18 H18 119.5 . .
C28 C29 C30 121.32(18) . .
C28 C29 H29 119.3 . .
C30 C29 H29 119.3 . .
C31 C30 C29 120.39(18) . .
C31 C30 H30 119.8 . .
C29 C30 H30 119.8 . .
C33 N5 C32 118.01(15) . .
C27 N11 C16 117.03(15) . .
C21 N12 C22 117.16(15) . .
C1 O7 C9 121.95(13) . .
C3 O1 H1O 109.5(14) . .
C8 O4 H4O 111.9(17) . .
C5 O2 H2O 104.0(16) . .
C13 O6 H6O 106.4(18) . .
C12 O5 H5O 111.0(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C1 1.391(2) .
C6 C5 1.416(2) .
C6 C7 1.425(2) .
C9 C8 1.362(2) .
C9 O7 1.373(2) .
C9 C10 1.464(2) .
C10 C15 1.396(2) .
C10 C11 1.398(2) .
C2 C1 1.379(2) .
C2 C3 1.389(2) .
C2 H2 0.9300 .
C7 O3 1.263(2) .
C7 C8 1.433(2) .
C11 C12 1.372(2) .
C11 H11 0.9300 .
C4 C5 1.365(2) .
C4 C3 1.397(2) .
C4 H4 0.9300 .
C1 O7 1.361(2) .
C32 N5 1.345(2) .
C32 C31 1.420(3) .
C32 C33 1.425(2) 2_665
C8 O4 1.354(2) .
C22 N12 1.342(2) .
C22 C23 1.422(3) .
C22 C27 1.429(2) .
C12 O5 1.367(2) .
C12 C13 1.398(2) .
C33 N5 1.342(2) .
C33 C28 1.416(3) 2_665
C33 C32 1.425(2) 2_665
C21 N12 1.340(2) .
C21 C20 1.424(3) .
C21 C16 1.429(2) .
C14 C15 1.382(2) .
C14 C13 1.384(2) .
C14 H14 0.9300 .
C16 N11 1.348(2) .
C16 C17 1.420(3) .
C27 N11 1.340(2) .
C27 C26 1.420(2) .
C17 C18 1.352(3) .
C17 H17 0.9300 .
C3 O1 1.346(2) .
C26 C25 1.348(3) .
C26 H26 0.9300 .
C31 C30 1.357(3) .
C31 H31 0.9300 .
C5 O2 1.355(2) .
C28 C29 1.351(3) .
C28 C33 1.416(3) 2_665
C28 H28 0.9300 .
C13 O6 1.358(2) .
C23 C24 1.355(3) .
C23 H23 0.9300 .
C20 C19 1.354(3) .
C20 H20 0.9300 .
C19 C18 1.419(3) .
C19 H19 0.9300 .
C15 H15 0.9300 .
C24 C25 1.416(3) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C18 H18 0.9300 .
C29 C30 1.418(3) .
C29 H29 0.9300 .
C30 H30 0.9300 .
O1 H1O 0.94(3) .
O4 H4O 0.85(3) .
O2 H2O 0.86(2) .
O6 H6O 0.89(3) .
O5 H5O 0.95(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O4 0.93 2.14 2.810(2) 128.2 .
C28 H28 O3 0.93 2.29 3.134(2) 150.8 1_454
O1 H1O N5 0.94(3) 1.81(3) 2.7363(19) 170(2) .
O5 H5O N12 0.95(3) 1.92(3) 2.861(2) 172(2) 1_566
O4 H4O N11 0.85(3) 2.06(3) 2.850(2) 154(2) 2_866
O2 H2O O3 0.86(2) 1.78(2) 2.5940(18) 155(2) .
O6 H6O O8 0.89(3) 1.83(3) 2.715(2) 174(3) .
