#------------------------------------------------------------------------------
#$Date: 2016-03-13 15:25:55 +0200 (Sun, 13 Mar 2016) $
#$Revision: 178180 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/28/1542806.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_1542806
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 O7'
_chemical_formula_weight         572.53
_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                112.21
_cell_angle_beta                 94.99
_cell_angle_gamma                94.92
_cell_formula_units_Z            2
_cell_length_a                   4.983
_cell_length_b                   15.381
_cell_length_c                   18.142
_cell_measurement_temperature    150(2)
_cell_volume                     1271.766
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13154
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.287
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow-Red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       Plate
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0614
_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)+(0.0589P)²+0.7384P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             5827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lc5063.cif
_cod_data_source_block           QPH_V
_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/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        1271.8
_cod_database_code               1542806
_publcif_datablock.id            {33f9d94e-8325-49eb-86a2-12ab23dfabbb}
_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   0.949
_shelx_estimated_absorpt_t_max   0.989
_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
H4O H 0.897(6) 0.450(2) 0.4194(19) 0.042(10) Uiso 1 1 d . .
H1O H -0.174(7) 0.193(2) 0.630(2) 0.054(11) Uiso 1 1 d . .
H6O H -0.063(7) 0.012(3) 0.130(2) 0.072(12) Uiso 1 1 d . .
H2O H 0.670(8) 0.464(3) 0.636(2) 0.083(13) Uiso 1 1 d . .
H5O H 0.244(8) 0.045(3) 0.003(2) 0.079(13) Uiso 1 1 d . .
O7 O 0.2104(3) 0.25172(12) 0.38109(10) 0.0204(4) Uani 1 1 d . .
O1 O -0.2108(4) 0.19263(14) 0.58067(12) 0.0272(5) Uani 1 1 d . .
O3 O 0.7715(4) 0.46014(12) 0.54083(10) 0.0244(4) Uani 1 1 d . .
O4 O 0.7986(4) 0.40741(13) 0.38125(11) 0.0252(4) Uani 1 1 d . .
O5 O 0.3775(4) 0.09770(14) 0.01924(10) 0.0296(5) Uani 1 1 d . .
N2 N 0.0032(4) -0.16528(15) 0.28287(12) 0.0221(5) Uani 1 1 d . .
C9 C 0.4138(5) 0.29309(17) 0.35368(14) 0.0175(5) Uani 1 1 d . .
O2 O 0.5513(4) 0.43142(14) 0.65876(11) 0.0306(5) Uani 1 1 d . .
N1 N -0.0912(4) -0.06573(15) 0.18209(12) 0.0224(5) Uani 1 1 d . .
C6 C 0.3897(5) 0.34630(17) 0.51830(14) 0.0191(5) Uani 1 1 d . .
C7 C 0.5949(5) 0.39461(17) 0.49231(15) 0.0199(5) Uani 1 1 d . .
O6 O -0.0124(4) 0.04668(13) 0.09713(10) 0.0256(4) Uani 1 1 d . .
C8 C 0.5994(5) 0.36415(17) 0.40681(15) 0.0196(5) Uani 1 1 d . .
C2 C -0.0035(5) 0.22486(18) 0.48112(15) 0.0206(5) Uani 1 1 d . .
H2 H -0.1316 0.1781 0.4408 0.025 Uiso 1 1 calc R U
C4 C 0.1705(5) 0.31474(18) 0.62144(15) 0.0227(6) Uani 1 1 d . .
H4 H 0.1575 0.3278 0.6764 0.027 Uiso 1 1 calc R U
C27 C 0.0690(5) -0.13487(18) 0.16318(15) 0.0215(6) Uani 1 1 d . .
C21 C -0.1638(5) -0.09730(18) 0.30031(15) 0.0215(6) Uani 1 1 d . .
C14 C 0.1823(5) 0.12182(17) 0.14121(14) 0.0189(5) Uani 1 1 d . .
C1 C 0.1995(5) 0.27576(17) 0.46122(14) 0.0189(5) Uani 1 1 d . .
C16 C -0.2116(5) -0.04736(18) 0.24869(15) 0.0205(6) Uani 1 1 d . .
C22 C 0.1179(5) -0.18541(18) 0.21487(15) 0.0218(6) Uani 1 1 d . .
C17 C -0.3922(5) 0.02267(18) 0.26890(15) 0.0238(6) Uani 1 1 d . .
H17 H -0.4254 0.0565 0.2355 0.029 Uiso 1 1 calc R U
C15 C 0.1911(5) 0.17187(17) 0.22267(14) 0.0187(5) Uani 1 1 d . .
H15 H 0.0541 0.1556 0.2502 0.022 Uiso 1 1 calc R U
C20 C -0.2963(5) -0.07494(19) 0.37051(16) 0.0252(6) Uani 1 1 d . .
H20 H -0.2648 -0.1068 0.4056 0.030 Uiso 1 1 calc R U
C18 C -0.5165(5) 0.04111(19) 0.33568(16) 0.0257(6) Uani 1 1 d . .
H18 H -0.6380 0.0875 0.3483 0.031 Uiso 1 1 calc R U
C12 C 0.5788(5) 0.22215(18) 0.14083(15) 0.0244(6) Uani 1 1 d . .
H12 H 0.7101 0.2401 0.1125 0.029 Uiso 1 1 calc R U
C13 C 0.3784(5) 0.14676(18) 0.09940(14) 0.0221(6) Uani 1 1 d . .
C23 C 0.2887(6) -0.25770(19) 0.19308(16) 0.0285(6) Uani 1 1 d . .
H23 H 0.3199 -0.2921 0.2262 0.034 Uiso 1 1 calc R U
C19 C -0.4681(5) -0.00774(19) 0.38712(16) 0.0266(6) Uani 1 1 d . .
H19 H -0.5570 0.0067 0.4338 0.032 Uiso 1 1 calc R U
C10 C 0.3992(5) 0.24667(17) 0.26594(14) 0.0177(5) Uani 1 1 d . .
C26 C 0.2002(6) -0.15778(19) 0.09290(15) 0.0280(6) Uani 1 1 d . .
H26 H 0.1740 -0.1243 0.0589 0.034 Uiso 1 1 calc R U
C11 C 0.5910(5) 0.27174(18) 0.22289(15) 0.0230(6) Uani 1 1 d . .
H11 H 0.7304 0.3231 0.2502 0.028 Uiso 1 1 calc R U
C3 C -0.0141(5) 0.24416(17) 0.56165(15) 0.0201(5) Uani 1 1 d . .
C5 C 0.3702(5) 0.36509(18) 0.60058(15) 0.0222(6) Uani 1 1 d . .
C25 C 0.3615(6) -0.2269(2) 0.07451(17) 0.0336(7) Uani 1 1 d . .
H25 H 0.4464 -0.2421 0.0271 0.040 Uiso 1 1 calc R U
C24 C 0.4077(6) -0.2779(2) 0.12505(17) 0.0339(7) Uani 1 1 d . .
H24 H 0.5226 -0.3263 0.1109 0.041 Uiso 1 1 calc R U
C33 C 0.9084(6) 0.5142(2) 0.07037(17) 0.0325(7) Uani 1 1 d . .
N3 N 0.8141(6) 0.5647(2) 0.02978(17) 0.0504(8) Uani 1 1 d . .
C28 C 1.0947(6) 0.4490(2) 0.04061(17) 0.0314(7) Uani 1 1 d . .
C30 C 1.0988(6) 0.4123(2) 0.15924(19) 0.0378(7) Uani 1 1 d . .
H30 H 1.1630 0.3780 0.1896 0.045 Uiso 1 1 calc R U
C31 C 0.9147(7) 0.4767(2) 0.18863(18) 0.0391(8) Uani 1 1 d . .
H31 H 0.8554 0.4863 0.2392 0.047 Uiso 1 1 calc R U
C32 C 0.8201(8) 0.5254(3) 0.1458(2) 0.0530(10) Uani 1 1 d . .
H32 H 0.6922 0.5680 0.1663 0.064 Uiso 1 1 calc R U
C29 C 1.1860(8) 0.3987(3) 0.0875(2) 0.0524(10) Uani 1 1 d . .
H29 H 1.3109 0.3545 0.0681 0.063 Uiso 1 1 calc R U
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
C1 O7 C9 121.52(19) .
C3 O1 H1O 113(2) .
C8 O4 H4O 112(2) .
C13 O5 H5O 108(2) .
C22 N2 C21 117.6(2) .
C8 C9 O7 120.0(2) .
C8 C9 C10 129.3(2) .
O7 C9 C10 110.7(2) .
C5 O2 H2O 111(2) .
C16 N1 C27 118.1(2) .
C1 C6 C5 117.3(2) .
C1 C6 C7 119.5(2) .
C5 C6 C7 123.2(2) .
O3 C7 C6 122.7(2) .
O3 C7 C8 120.2(2) .
C6 C7 C8 117.0(2) .
C14 O6 H6O 109(2) .
O4 C8 C9 121.1(2) .
O4 C8 C7 117.7(2) .
C9 C8 C7 121.2(2) .
C1 C2 C3 117.9(2) .
C1 C2 H2 121.1 .
C3 C2 H2 121.1 .
C5 C4 C3 120.1(2) .
C5 C4 H4 120.0 .
C3 C4 H4 120.0 .
N1 C27 C26 120.4(2) .
N1 C27 C22 120.8(2) .
C26 C27 C22 118.7(2) .
N2 C21 C20 119.9(2) .
N2 C21 C16 120.9(2) .
C20 C21 C16 119.1(2) .
O6 C14 C15 123.3(2) .
O6 C14 C13 116.8(2) .
C15 C14 C13 120.0(2) .
O7 C1 C2 116.1(2) .
O7 C1 C6 120.7(2) .
C2 C1 C6 123.2(2) .
N1 C16 C17 119.7(2) .
N1 C16 C21 121.3(2) .
C17 C16 C21 118.9(2) .
N2 C22 C23 119.6(2) .
N2 C22 C27 121.2(2) .
C23 C22 C27 119.2(2) .
C18 C17 C16 120.1(2) .
C18 C17 H17 119.9 .
C16 C17 H17 119.9 .
C14 C15 C10 121.4(2) .
C14 C15 H15 119.3 .
C10 C15 H15 119.3 .
C19 C20 C21 119.8(2) .
C19 C20 H20 120.1 .
C21 C20 H20 120.1 .
C17 C18 C19 121.1(3) .
C17 C18 H18 119.5 .
C19 C18 H18 119.5 .
C13 C12 C11 121.1(2) .
C13 C12 H12 119.5 .
C11 C12 H12 119.5 .
O5 C13 C12 119.5(2) .
O5 C13 C14 121.3(2) .
C12 C13 C14 119.2(2) .
C24 C23 C22 120.1(3) .
C24 C23 H23 119.9 .
C22 C23 H23 119.9 .
C20 C19 C18 120.9(3) .
C20 C19 H19 119.5 .
C18 C19 H19 119.5 .
C11 C10 C15 117.9(2) .
C11 C10 C9 122.5(2) .
C15 C10 C9 119.6(2) .
C25 C26 C27 120.1(3) .
C25 C26 H26 119.9 .
C27 C26 H26 119.9 .
C12 C11 C10 120.5(2) .
C12 C11 H11 119.7 .
C10 C11 H11 119.7 .
O1 C3 C2 117.5(2) .
O1 C3 C4 121.2(2) .
C2 C3 C4 121.3(2) .
O2 C5 C4 119.5(2) .
O2 C5 C6 120.2(2) .
C4 C5 C6 120.2(2) .
C26 C25 C24 121.3(3) .
C26 C25 H25 119.4 .
C24 C25 H25 119.4 .
C23 C24 C25 120.5(3) .
C23 C24 H24 119.7 .
C25 C24 H24 119.7 .
N3 C33 C28 122.0(3) .
N3 C33 C32 120.0(3) .
C28 C33 C32 118.1(3) .
C28 N3 C33 117.1(3) 2_765
N3 C28 C33 121.0(3) 2_765
N3 C28 C29 120.5(3) 2_765
C33 C28 C29 118.5(3) .
C29 C30 C31 120.1(3) .
C29 C30 H30 119.9 .
C31 C30 H30 119.9 .
C32 C31 C30 120.5(3) .
C32 C31 H31 119.7 .
C30 C31 H31 119.7 .
C31 C32 C33 121.4(3) .
C31 C32 H32 119.3 .
C33 C32 H32 119.3 .
C30 C29 C28 121.4(3) .
C30 C29 H29 119.3 .
C28 C29 H29 119.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C1 1.365(3) .
O7 C9 1.377(3) .
O1 C3 1.357(3) .
O1 H1O 0.90(3) .
O3 C7 1.268(3) .
O4 C8 1.357(3) .
O4 H4O 0.83(3) .
O5 C13 1.361(3) .
O5 H5O 0.94(4) .
N2 C22 1.345(3) .
N2 C21 1.353(3) .
C9 C8 1.362(3) .
C9 C10 1.470(3) .
O2 C5 1.353(3) .
O2 H2O 0.96(4) .
N1 C16 1.340(3) .
N1 C27 1.343(3) .
C6 C1 1.397(3) .
C6 C5 1.423(3) .
C6 C7 1.428(3) .
C7 C8 1.444(3) .
O6 C14 1.375(3) .
O6 H6O 0.98(4) .
C2 C1 1.381(3) .
C2 C3 1.383(3) .
C2 H2 0.9500 .
C4 C5 1.374(4) .
C4 C3 1.402(4) .
C4 H4 0.9500 .
C27 C26 1.422(4) .
C27 C22 1.445(3) .
C21 C20 1.425(3) .
C21 C16 1.435(3) .
C14 C15 1.379(3) .
C14 C13 1.401(3) .
C16 C17 1.425(4) .
C22 C23 1.416(4) .
C17 C18 1.354(4) .
C17 H17 0.9500 .
C15 C10 1.409(3) .
C15 H15 0.9500 .
C20 C19 1.362(4) .
C20 H20 0.9500 .
C18 C19 1.420(4) .
C18 H18 0.9500 .
C12 C13 1.385(4) .
C12 C11 1.386(3) .
C12 H12 0.9500 .
C23 C24 1.357(4) .
C23 H23 0.9500 .
C19 H19 0.9500 .
C10 C11 1.402(3) .
C26 C25 1.347(4) .
C26 H26 0.9500 .
C11 H11 0.9500 .
C25 C24 1.431(4) .
C25 H25 0.9500 .
C24 H24 0.9500 .
C33 N3 1.341(4) .
C33 C28 1.413(4) .
C33 C32 1.427(4) .
N3 C28 1.340(4) 2_765
C28 N3 1.340(4) 2_765
C28 C29 1.422(4) .
C30 C29 1.355(4) .
C30 C31 1.396(4) .
C30 H30 0.9500 .
C31 C32 1.351(4) .
C31 H31 0.9500 .
C32 H32 0.9500 .
C29 H29 0.9500 .
