#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545846.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_1545846
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            'C44 H44 N6 O6'
_chemical_formula_weight         752.85
_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                95.009(14)
_cell_angle_beta                 95.415(11)
_cell_angle_gamma                101.04(2)
_cell_formula_units_Z            1
_cell_length_a                   7.812(9)
_cell_length_b                   8.763(10)
_cell_length_c                   14.300(16)
_cell_measurement_temperature    150(2)
_cell_volume                     950.9(19)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10088
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_min         1.439
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       Block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0518
_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)+(0.0917P)²+0.1007P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3654
_reflns_number_total             4348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           QS_PGL_TMP_PHE_DPE
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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               1545846
_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   0.945
_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
H22B H -0.576(4) 0.421(4) 1.077(2) 0.087(9) Uiso 1 1 d . .
H22A H -0.457(3) 0.603(3) 1.088(2) 0.072(8) Uiso 1 1 d . .
O1 O 0.06489(15) 0.14728(14) 0.67499(9) 0.0384(3) Uani 1 1 d . .
H1O H 0.0590 0.2187 0.6400 0.058 Uiso 1 1 calc R U
O2 O -0.25825(16) -0.12950(14) 0.89622(8) 0.0369(3) Uani 1 1 d . .
H2O H -0.1731 -0.1753 0.8973 0.055 Uiso 1 1 calc R U
O3 O -0.50913(15) 0.23058(15) 0.73087(9) 0.0374(3) Uani 1 1 d . .
H3O H -0.4979 0.2785 0.6827 0.056 Uiso 1 1 calc R U
C6 C -0.22141(19) 0.19463(16) 0.70024(10) 0.0265(3) Uani 1 1 d . .
H6 H -0.2152 0.2682 0.6550 0.032 Uiso 1 1 calc R U
C2 C -0.0905(2) 0.01131(17) 0.78597(11) 0.0282(3) Uani 1 1 d . .
H2 H 0.0052 -0.0389 0.7994 0.034 Uiso 1 1 calc R U
C4 C -0.3798(2) 0.05217(17) 0.81357(10) 0.0286(3) Uani 1 1 d . .
H4 H -0.4815 0.0291 0.8455 0.034 Uiso 1 1 calc R U
C1 C -0.08287(19) 0.11928(16) 0.71986(11) 0.0266(3) Uani 1 1 d . .
C5 C -0.36904(19) 0.16068(17) 0.74777(11) 0.0271(3) Uani 1 1 d . .
C3 C -0.2401(2) -0.02197(17) 0.83202(10) 0.0273(3) Uani 1 1 d . .
N3 N -0.0059(2) 0.29841(17) 1.09074(10) 0.0383(4) Uani 1 1 d . .
C18 C -0.1447(2) 0.5198(2) 1.10294(12) 0.0380(4) Uani 1 1 d . .
H18 H -0.1335 0.6287 1.1205 0.046 Uiso 1 1 calc R U
C20 C -0.3129(3) 0.2705(2) 1.03948(12) 0.0403(4) Uani 1 1 d . .
H20 H -0.4201 0.2038 1.0128 0.048 Uiso 1 1 calc R U
C19 C -0.3066(2) 0.4291(2) 1.06520(11) 0.0374(4) Uani 1 1 d . .
C17 C 0.0006(2) 0.4510(2) 1.11491(12) 0.0384(4) Uani 1 1 d . .
H17 H 0.1097 0.5148 1.1415 0.046 Uiso 1 1 calc R U
C21 C -0.1626(3) 0.2121(2) 1.05310(12) 0.0405(4) Uani 1 1 d . .
H21 H -0.1696 0.1040 1.0348 0.049 Uiso 1 1 calc R U
C22 C -0.4707(3) 0.4951(3) 1.05194(13) 0.0454(5) Uani 1 1 d . .
N1 N 0.47831(16) 0.59520(14) 0.42967(9) 0.0265(3) Uani 1 1 d . .
C7 C 0.3074(2) 0.3799(2) 0.32048(12) 0.0370(4) Uani 1 1 d . .
H7A H 0.3253 0.4612 0.2774 0.055 Uiso 1 1 calc R U
H7B H 0.1822 0.3507 0.3276 0.055 Uiso 1 1 calc R U
H7C H 0.3487 0.2880 0.2946 0.055 Uiso 1 1 calc R U
C8 C 0.40889(19) 0.44127(17) 0.41530(10) 0.0256(3) Uani 1 1 d . .
C9 C 0.56859(18) 0.65521(16) 0.51370(11) 0.0251(3) Uani 1 1 d . .
C10 C 0.6414(2) 0.82867(18) 0.52753(13) 0.0371(4) Uani 1 1 d . .
H10A H 0.6201 0.8733 0.4680 0.056 Uiso 1 1 calc R U
H10B H 0.7680 0.8477 0.5472 0.056 Uiso 1 1 calc R U
H10C H 0.5835 0.8779 0.5764 0.056 Uiso 1 1 calc R U
N2 N 0.03971(17) 0.37846(14) 0.55175(9) 0.0271(3) Uani 1 1 d . .
C13 C 0.10393(19) 0.53013(16) 0.58380(10) 0.0253(3) Uani 1 1 d . .
C12 C 0.2134(2) 0.56851(18) 0.67155(11) 0.0310(3) Uani 1 1 d . .
H12 H 0.2417 0.4881 0.7069 0.037 Uiso 1 1 calc R U
C14 C -0.06428(19) 0.34700(17) 0.46911(11) 0.0265(3) Uani 1 1 d . .
C16 C -0.2371(2) 0.15554(18) 0.34724(12) 0.0334(4) Uani 1 1 d . .
H16 H -0.2826 0.0497 0.3227 0.040 Uiso 1 1 calc R U
C15 C -0.1340(2) 0.18854(17) 0.43183(12) 0.0315(4) Uani 1 1 d . .
H15 H -0.1085 0.1058 0.4660 0.038 Uiso 1 1 calc R U
C11 C 0.2771(2) 0.7220(2) 0.70436(12) 0.0340(4) Uani 1 1 d . .
H11 H 0.3497 0.7474 0.7629 0.041 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
C1 O1 H1O 109.5 . .
C3 O2 H2O 109.5 . .
C5 O3 H3O 109.5 . .
C5 C6 C1 119.01(15) . .
C5 C6 H6 120.5 . .
C1 C6 H6 120.5 . .
C3 C2 C1 119.02(14) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C3 C4 C5 119.18(15) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
O1 C1 C6 121.58(15) . .
O1 C1 C2 117.42(14) . .
C6 C1 C2 121.00(15) . .
O3 C5 C6 121.44(15) . .
O3 C5 C4 117.67(14) . .
C6 C5 C4 120.89(14) . .
O2 C3 C4 116.93(14) . .
O2 C3 C2 122.17(14) . .
C4 C3 C2 120.90(15) . .
C17 N3 C21 116.70(16) . .
C17 C18 C19 119.85(18) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C21 C20 C19 119.34(18) . .
C21 C20 H20 120.3 . .
C19 C20 H20 120.3 . .
C18 C19 C20 117.05(17) . .
C18 C19 C22 122.81(18) . .
C20 C19 C22 120.14(18) . .
N3 C17 C18 123.03(17) . .
N3 C17 H17 118.5 . .
C18 C17 H17 118.5 . .
N3 C21 C20 124.02(18) . .
N3 C21 H21 118.0 . .
C20 C21 H21 118.0 . .
C19 C22 C22 112.4(2) . 2_467
C19 C22 H22B 109.7(16) . .
C22 C22 H22B 106.1(16) 2_467 .
C19 C22 H22A 112.4(15) . .
C22 C22 H22A 108.5(16) 2_467 .
H22B C22 H22A 107(2) . .
C9 N1 C8 119.01(13) . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 120.54(14) . 2_666
N1 C8 C7 117.04(13) . .
C9 C8 C7 122.42(15) 2_666 .
N1 C9 C8 120.44(15) . 2_666
N1 C9 C10 117.33(14) . .
C8 C9 C10 122.23(15) 2_666 .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C14 N2 C13 117.66(13) . .
N2 C13 C12 119.42(13) . .
N2 C13 C14 121.06(15) . 2_566
C12 C13 C14 119.52(15) . 2_566
C11 C12 C13 119.41(14) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
N2 C14 C15 119.77(14) . .
N2 C14 C13 121.28(14) . 2_566
C15 C14 C13 118.94(16) . 2_566
C15 C16 C11 120.56(15) . 2_566
C15 C16 H16 119.7 . .
C11 C16 H16 119.7 2_566 .
C16 C15 C14 120.16(14) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C12 C11 C16 121.40(17) . 2_566
C12 C11 H11 119.3 . .
C16 C11 H11 119.3 2_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.365(2) .
O1 H1O 0.8400 .
O2 C3 1.369(2) .
O2 H2O 0.8400 .
O3 C5 1.365(2) .
O3 H3O 0.8400 .
C6 C5 1.390(3) .
C6 C1 1.391(2) .
C6 H6 0.9500 .
C2 C3 1.391(3) .
C2 C1 1.392(2) .
C2 H2 0.9500 .
C4 C3 1.389(2) .
C4 C5 1.392(2) .
C4 H4 0.9500 .
N3 C17 1.341(3) .
N3 C21 1.345(3) .
C18 C17 1.387(3) .
C18 C19 1.391(3) .
C18 H18 0.9500 .
C20 C21 1.373(3) .
C20 C19 1.397(3) .
C20 H20 0.9500 .
C19 C22 1.507(3) .
C17 H17 0.9500 .
C21 H21 0.9500 .
C22 C22 1.527(4) 2_467
C22 H22B 1.06(3) .
C22 H22A 1.02(3) .
N1 C9 1.344(2) .
N1 C8 1.344(2) .
C7 C8 1.504(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.396(2) 2_666
C9 C8 1.396(2) 2_666
C9 C10 1.506(3) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
N2 C14 1.345(2) .
N2 C13 1.350(2) .
C13 C12 1.426(2) .
C13 C14 1.433(2) 2_566
C12 C11 1.366(3) .
C12 H12 0.9500 .
C14 C15 1.426(2) .
C14 C13 1.433(2) 2_566
C16 C15 1.365(3) .
C16 C11 1.420(3) 2_566
C16 H16 0.9500 .
C15 H15 0.9500 .
C11 C16 1.420(3) 2_566
C11 H11 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
O1 H1O N2 0.84 1.98 2.821(3) 176.9 .
O2 H2O N3 0.84 1.93 2.762(3) 172.8 2_557
O3 H3O N1 0.84 2.03 2.870(3) 176.4 2_566
C6 H6 N2 0.95 2.67 3.379(3) 131.6 .
O1 H1O N2 0.84 1.98 2.821(3) 176.9 .
O2 H2O N3 0.84 1.93 2.762(3) 172.8 2_557
O3 H3O N1 0.84 2.03 2.870(3) 176.4 2_566
C6 H6 N2 0.95 2.67 3.379(3) 131.6 .
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
C5 C6 C1 O1 179.61(14) . .
C5 C6 C1 C2 0.0(2) . .
C3 C2 C1 O1 -179.02(13) . .
C3 C2 C1 C6 0.6(2) . .
C1 C6 C5 O3 -179.64(13) . .
C1 C6 C5 C4 -0.5(2) . .
C3 C4 C5 O3 179.56(13) . .
C3 C4 C5 C6 0.4(2) . .
C5 C4 C3 O2 -179.01(13) . .
C5 C4 C3 C2 0.2(2) . .
C1 C2 C3 O2 178.47(13) . .
C1 C2 C3 C4 -0.7(2) . .
C17 C18 C19 C20 -1.1(2) . .
C17 C18 C19 C22 178.76(16) . .
C21 C20 C19 C18 0.6(2) . .
C21 C20 C19 C22 -179.23(17) . .
C21 N3 C17 C18 0.2(2) . .
C19 C18 C17 N3 0.7(3) . .
C17 N3 C21 C20 -0.7(3) . .
C19 C20 C21 N3 0.3(3) . .
C18 C19 C22 C22 108.6(3) . 2_467
C20 C19 C22 C22 -71.6(3) . 2_467
C9 N1 C8 C9 -0.5(2) . 2_666
C9 N1 C8 C7 179.39(13) . .
C8 N1 C9 C8 0.5(2) . 2_666
C8 N1 C9 C10 -178.91(13) . .
C14 N2 C13 C12 179.42(13) . .
C14 N2 C13 C14 -0.8(2) . 2_566
N2 C13 C12 C11 -179.45(14) . .
C14 C13 C12 C11 0.7(2) 2_566 .
C13 N2 C14 C15 179.39(13) . .
C13 N2 C14 C13 0.8(2) . 2_566
C11 C16 C15 C14 -0.3(2) 2_566 .
N2 C14 C15 C16 -178.89(14) . .
C13 C14 C15 C16 -0.2(2) 2_566 .
C13 C12 C11 C16 -0.2(2) . 2_566
