#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545847.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_1545847
loop_
_publ_author_name
'Dubey, Ritesh'
'Mir, Niyaz A.'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quaternary cocrystals: combinatorial synthetic strategies based on
 long-range synthon Aufbau modules (LSAM)
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              102
_journal_page_last               107
_journal_paper_doi               10.1107/S2052252515023957
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C56 H56 N6 O8'
_chemical_formula_weight         941.06
_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                102.012(3)
_cell_angle_beta                 105.153(3)
_cell_angle_gamma                112.368(3)
_cell_formula_units_Z            1
_cell_length_a                   10.1510(11)
_cell_length_b                   11.2084(12)
_cell_length_c                   12.3363(13)
_cell_measurement_temperature    150(2)
_cell_volume                     1176.1(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42928
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.215
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Bruker, AXS, 2008'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       Block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.220
_refine_diff_density_max         1.115
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.1045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1504P)²+12.4077P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4103
_refine_ls_wR_factor_ref         0.4122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3988
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           QS_PGL_TMP_PHE_PYR_hydrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1545847
_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   0.936
_shelx_estimated_absorpt_t_max   0.981
_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
O4 O 1.1503(6) 0.3103(5) 0.5643(4) 0.0288(11) Uani 1 1 d . .
H4A H 1.181(9) 0.413(9) 0.626(7) 0.03(2) Uiso 1 1 d . .
N2 N 0.3966(6) 0.8030(5) 0.1875(4) 0.0172(10) Uani 1 1 d . .
N1 N 0.6183(6) 0.7451(5) 0.3122(4) 0.0190(11) Uani 1 1 d . .
C7 C 0.4685(7) 0.6546(6) 0.2730(5) 0.0183(12) Uani 1 1 d . .
C10 C 0.6577(7) 0.8631(6) 0.2909(5) 0.0176(12) Uani 1 1 d . .
C14 C 0.8257(7) 0.9640(6) 0.3384(6) 0.0224(13) Uani 1 1 d . .
H14A H 0.8865 0.9270 0.3824 0.034 Uiso 1 1 calc R U
H14B H 0.8435 1.0512 0.3921 0.034 Uiso 1 1 calc R U
H14C H 0.8564 0.9794 0.2715 0.034 Uiso 1 1 calc R U
C13 C 0.5858(7) 1.0212(7) 0.1969(6) 0.0239(13) Uani 1 1 d . .
H13A H 0.4915 1.0227 0.1522 0.036 Uiso 1 1 calc R U
H13B H 0.6487 1.0249 0.1482 0.036 Uiso 1 1 calc R U
H13C H 0.6439 1.1008 0.2712 0.036 Uiso 1 1 calc R U
C9 C 0.5451(7) 0.8919(6) 0.2259(5) 0.0167(12) Uani 1 1 d . .
C8 C 0.3557(7) 0.6846(6) 0.2102(5) 0.0166(12) Uani 1 1 d . .
C12 C 0.1877(7) 0.5857(7) 0.1638(6) 0.0256(14) Uani 1 1 d . .
H12A H 0.1271 0.6277 0.1279 0.038 Uiso 1 1 calc R U
H12B H 0.1599 0.5632 0.2299 0.038 Uiso 1 1 calc R U
H12C H 0.1662 0.5015 0.1032 0.038 Uiso 1 1 calc R U
C11 C 0.4284(8) 0.5230(7) 0.2988(6) 0.0270(14) Uani 1 1 d . .
H11A H 0.5230 0.5197 0.3398 0.041 Uiso 1 1 calc R U
H11B H 0.3674 0.4449 0.2235 0.041 Uiso 1 1 calc R U
H11C H 0.3686 0.5184 0.3500 0.041 Uiso 1 1 calc R U
O1 O 0.8147(5) 0.4578(5) 0.2637(4) 0.0223(10) Uani 1 1 d . .
H1 H 0.7506 0.4601 0.2062 0.033 Uiso 1 1 calc R U
O2 O 1.1337(5) 0.2404(5) 0.3394(4) 0.0233(10) Uani 1 1 d . .
H2 H 1.1445 0.2766 0.4101 0.035 Uiso 1 1 calc R U
O3 O 0.8272(5) 0.1413(5) -0.0574(4) 0.0224(10) Uani 1 1 d . .
H3 H 0.7546 0.1520 -0.0976 0.034 Uiso 1 1 calc R U
C6 C 0.8161(6) 0.3005(6) 0.1005(5) 0.0156(12) Uani 1 1 d . .
H6 H 0.7433 0.3142 0.0450 0.019 Uiso 1 1 calc R U
C4 C 0.9816(7) 0.1942(6) 0.1423(5) 0.0194(12) Uani 1 1 d . .
H4 H 1.0229 0.1361 0.1152 0.023 Uiso 1 1 calc R U
C2 C 0.9723(6) 0.3501(6) 0.3065(5) 0.0153(11) Uani 1 1 d . .
H2A H 1.0047 0.3961 0.3897 0.018 Uiso 1 1 calc R U
C3 C 1.0281(6) 0.2615(6) 0.2630(5) 0.0150(11) Uani 1 1 d . .
C21 C 1.5274(7) 0.0635(6) 0.4896(5) 0.0165(12) Uani 1 1 d . .
C5 C 0.8731(6) 0.2124(6) 0.0602(5) 0.0162(12) Uani 1 1 d . .
C20 C 1.6882(7) 0.1537(6) 0.5375(5) 0.0202(13) Uani 1 1 d . .
C16 C 1.4228(7) 0.0998(6) 0.4213(5) 0.0203(13) Uani 1 1 d . .
C1 C 0.8660(6) 0.3673(6) 0.2208(5) 0.0148(11) Uani 1 1 d . .
C19 C 1.7403(8) 0.2778(6) 0.5163(6) 0.0238(13) Uani 1 1 d . .
H19 H 1.8474 0.3386 0.5478 0.029 Uiso 1 1 calc R U
C17 C 1.4814(8) 0.2267(7) 0.4035(6) 0.0252(14) Uani 1 1 d . .
H17 H 1.4126 0.2531 0.3589 0.030 Uiso 1 1 calc R U
C15 C 1.2622(7) 0.0064(7) 0.3744(6) 0.0229(13) Uani 1 1 d . .
H15 H 1.1912 0.0301 0.3289 0.028 Uiso 1 1 calc R U
C22 C 1.7909(7) 0.1138(7) 0.6070(6) 0.0235(13) Uani 1 1 d . .
H22 H 1.8983 0.1737 0.6403 0.028 Uiso 1 1 calc R U
C18 C 1.6376(8) 0.3134(7) 0.4499(6) 0.0275(15) Uani 1 1 d . .
H18 H 1.6751 0.3982 0.4362 0.033 Uiso 1 1 calc R U
N3 N 0.6120(6) 0.4810(5) 0.0789(4) 0.0189(11) Uani 1 1 d . .
C23 C 0.4639(7) 0.3857(6) 0.0304(5) 0.0181(12) Uani 1 1 d . .
C26 C 0.6497(7) 0.5937(6) 0.0486(5) 0.0171(12) Uani 1 1 d . .
C24 C 0.4195(8) 0.2629(7) 0.0597(6) 0.0230(13) Uani 1 1 d . .
H24 H 0.4950 0.2484 0.1113 0.028 Uiso 1 1 calc R U
C27 C 0.8063(7) 0.6977(7) 0.0961(6) 0.0240(13) Uani 1 1 d . .
H27 H 0.8840 0.6872 0.1495 0.029 Uiso 1 1 calc R U
C28 C 0.8431(8) 0.8120(7) 0.0644(6) 0.0269(14) Uani 1 1 d . .
H28 H 0.9475 0.8801 0.0953 0.032 Uiso 1 1 calc R U
C25 C 0.2710(8) 0.1679(7) 0.0141(6) 0.0261(14) Uani 1 1 d . .
H25 H 0.2419 0.0870 0.0344 0.031 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
_geom_angle_site_symmetry_3
C9 N2 C8 119.6(5) . .
C10 N1 C7 119.3(5) . .
N1 C7 C8 120.1(5) . .
N1 C7 C11 117.9(5) . .
C8 C7 C11 122.1(6) . .
N1 C10 C9 120.6(5) . .
N1 C10 C14 118.3(5) . .
C9 C10 C14 121.1(5) . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N2 C9 C10 120.2(5) . .
N2 C9 C13 117.9(5) . .
C10 C9 C13 121.9(5) . .
N2 C8 C7 120.2(5) . .
N2 C8 C12 118.1(5) . .
C7 C8 C12 121.6(5) . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C1 O1 H1 109.5 . .
C3 O2 H2 109.5 . .
C5 O3 H3 109.5 . .
C1 C6 C5 119.4(5) . .
C1 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C3 C4 C5 119.3(5) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C3 C2 C1 116.5(5) . .
C3 C2 H2A 121.7 . .
C1 C2 H2A 121.7 . .
O2 C3 C4 117.2(5) . .
O2 C3 C2 120.6(5) . .
C4 C3 C2 122.1(5) . .
C16 C21 C20 120.1(6) . .
C16 C21 C21 120.3(7) . 2_856
C20 C21 C21 119.6(7) . 2_856
O3 C5 C6 122.6(5) . .
O3 C5 C4 117.5(5) . .
C6 C5 C4 119.9(5) . .
C19 C20 C21 119.0(6) . .
C19 C20 C22 122.4(6) . .
C21 C20 C22 118.6(6) . .
C17 C16 C21 118.6(6) . .
C17 C16 C15 122.9(6) . .
C21 C16 C15 118.5(6) . .
C6 C1 O1 120.9(5) . .
C6 C1 C2 122.7(5) . .
O1 C1 C2 116.4(5) . .
C18 C19 C20 120.8(6) . .
C18 C19 H19 119.6 . .
C20 C19 H19 119.6 . .
C18 C17 C16 120.9(6) . .
C18 C17 H17 119.5 . .
C16 C17 H17 119.5 . .
C22 C15 C16 121.8(6) 2_856 .
C22 C15 H15 119.1 2_856 .
C16 C15 H15 119.1 . .
C15 C22 C20 121.2(6) 2_856 .
C15 C22 H22 119.4 2_856 .
C20 C22 H22 119.4 . .
C17 C18 C19 120.6(6) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C26 N3 C23 117.7(5) . .
N3 C23 C26 120.8(6) . 2_665
N3 C23 C24 119.3(5) . .
C26 C23 C24 119.8(6) 2_665 .
N3 C26 C23 121.4(6) . 2_665
N3 C26 C27 120.2(5) . .
C23 C26 C27 118.4(6) 2_665 .
C25 C24 C23 120.1(6) . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C28 C27 C26 119.6(6) . .
C28 C27 H27 120.2 . .
C26 C27 H27 120.2 . .
C27 C28 C25 121.6(6) . 2_665
C27 C28 H28 119.2 . .
C25 C28 H28 119.2 2_665 .
C24 C25 C28 120.4(6) . 2_665
C24 C25 H25 119.8 . .
C28 C25 H25 119.8 2_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 H4A 1.11(8) .
N2 C9 1.333(8) .
N2 C8 1.344(8) .
N1 C10 1.333(8) .
N1 C7 1.347(8) .
C7 C8 1.401(8) .
C7 C11 1.499(8) .
C10 C9 1.401(8) .
C10 C14 1.504(8) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C13 C9 1.496(8) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C8 C12 1.501(8) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
O1 C1 1.379(7) .
O1 H1 0.8400 .
O2 C3 1.361(7) .
O2 H2 0.8400 .
O3 C5 1.356(7) .
O3 H3 0.8400 .
C6 C1 1.369(8) .
C6 C5 1.392(8) .
C6 H6 0.9500 .
C4 C3 1.380(8) .
C4 C5 1.398(8) .
C4 H4 0.9500 .
C2 C3 1.400(8) .
C2 C1 1.402(8) .
C2 H2A 0.9500 .
C21 C16 1.416(8) .
C21 C20 1.424(9) .
C21 C21 1.422(12) 2_856
C20 C19 1.395(9) .
C20 C22 1.438(9) .
C16 C17 1.407(9) .
C16 C15 1.429(9) .
C19 C18 1.387(10) .
C19 H19 0.9500 .
C17 C18 1.381(10) .
C17 H17 0.9500 .
C15 C22 1.341(9) 2_856
C15 H15 0.9500 .
C22 C15 1.341(9) 2_856
C22 H22 0.9500 .
C18 H18 0.9500 .
N3 C26 1.336(8) .
N3 C23 1.342(8) .
C23 C26 1.429(8) 2_665
C23 C24 1.431(9) .
C26 C23 1.429(8) 2_665
C26 C27 1.431(9) .
C24 C25 1.345(10) .
C24 H24 0.9500 .
C27 C28 1.362(9) .
C27 H27 0.9500 .
C28 C25 1.425(10) 2_665
C28 H28 0.9500 .
C25 C28 1.425(10) 2_665
C25 H25 0.9500 .
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
O4 H4A O1 1.11(8) 1.75(8) 2.828(6) 162(7) 2_766
O1 H1 N3 0.84 1.94 2.775(6) 175.5 .
O2 H2 O4 0.84 1.84 2.662(6) 165.3 .
O3 H3 N2 0.84 1.94 2.779(6) 173.7 2_665
C6 H6 N2 0.95 2.62 3.317(7) 130.7 2_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C10 N1 C7 C8 0.2(8) . .
C10 N1 C7 C11 -179.9(5) . .
C7 N1 C10 C9 -1.6(8) . .
C7 N1 C10 C14 178.5(5) . .
C8 N2 C9 C10 -0.9(8) . .
C8 N2 C9 C13 178.9(5) . .
N1 C10 C9 N2 2.0(9) . .
C14 C10 C9 N2 -178.1(5) . .
N1 C10 C9 C13 -177.8(5) . .
C14 C10 C9 C13 2.1(9) . .
C9 N2 C8 C7 -0.4(8) . .
C9 N2 C8 C12 -178.9(5) . .
N1 C7 C8 N2 0.8(8) . .
C11 C7 C8 N2 -179.1(5) . .
N1 C7 C8 C12 179.2(5) . .
C11 C7 C8 C12 -0.7(9) . .
C5 C4 C3 O2 179.9(5) . .
C5 C4 C3 C2 -1.2(9) . .
C1 C2 C3 O2 178.8(5) . .
C1 C2 C3 C4 0.0(8) . .
C1 C6 C5 O3 179.0(5) . .
C1 C6 C5 C4 -0.8(8) . .
C3 C4 C5 O3 -178.1(5) . .
C3 C4 C5 C6 1.6(9) . .
C16 C21 C20 C19 0.2(9) . .
C21 C21 C20 C19 179.9(6) 2_856 .
C16 C21 C20 C22 179.7(5) . .
C21 C21 C20 C22 -0.6(10) 2_856 .
C20 C21 C16 C17 -0.7(9) . .
C21 C21 C16 C17 179.6(6) 2_856 .
C20 C21 C16 C15 179.8(5) . .
C21 C21 C16 C15 0.2(10) 2_856 .
C5 C6 C1 O1 178.5(5) . .
C5 C6 C1 C2 -0.5(9) . .
C3 C2 C1 C6 0.9(8) . .
C3 C2 C1 O1 -178.1(5) . .
C21 C20 C19 C18 0.1(9) . .
C22 C20 C19 C18 -179.4(6) . .
C21 C16 C17 C18 1.0(9) . .
C15 C16 C17 C18 -179.6(6) . .
C17 C16 C15 C22 -179.7(6) . 2_856
C21 C16 C15 C22 -0.4(9) . 2_856
C19 C20 C22 C15 -179.7(6) . 2_856
C21 C20 C22 C15 0.8(9) . 2_856
C16 C17 C18 C19 -0.7(10) . .
C20 C19 C18 C17 0.1(10) . .
C26 N3 C23 C26 -1.5(9) . 2_665
C26 N3 C23 C24 179.3(5) . .
C23 N3 C26 C23 1.5(9) . 2_665
C23 N3 C26 C27 -179.1(5) . .
N3 C23 C24 C25 178.4(6) . .
C26 C23 C24 C25 -0.8(9) 2_665 .
N3 C26 C27 C28 179.9(6) . .
C23 C26 C27 C28 -0.6(9) 2_665 .
C26 C27 C28 C25 0.9(10) . 2_665
C23 C24 C25 C28 0.6(10) . 2_665
