#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545844.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_1545844
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            'C62 H54 N6 O4'
_chemical_formula_weight         947.11
_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                107.761(8)
_cell_angle_beta                 101.019(7)
_cell_angle_gamma                91.432(6)
_cell_formula_units_Z            1
_cell_length_a                   9.034(2)
_cell_length_b                   9.889(2)
_cell_length_c                   14.505(4)
_cell_measurement_temperature    150(2)
_cell_volume                     1206.5(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0408
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12197
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow-Red
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       Plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0731P)²+0.3701P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3640
_reflns_number_total             5504
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           QS_ORC_TMP_PHE_PYR
_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               1545844
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
_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
H2O H 0.250(3) 0.278(3) 0.0299(19) 0.053(8) Uiso 1 1 d . .
H1O H 0.238(3) 0.595(3) 0.330(2) 0.074(9) Uiso 1 1 d . .
N1 N 0.39533(17) 0.68009(16) 0.29807(12) 0.0267(4) Uani 1 1 d . .
O1 O 0.16264(17) 0.54186(15) 0.34748(11) 0.0350(4) Uani 1 1 d . .
O2 O 0.18504(17) 0.20716(16) 0.03057(11) 0.0352(4) Uani 1 1 d . .
N2 N 0.63383(19) 0.80472(18) 0.24066(13) 0.0318(4) Uani 1 1 d . .
C19 C 0.6616(2) 0.7355(2) 0.30794(15) 0.0281(4) Uani 1 1 d . .
C15 C 0.5776(2) 0.5977(2) 0.40755(15) 0.0308(5) Uani 1 1 d . .
H15 H 0.4987 0.5557 0.4275 0.037 Uiso 1 1 calc R U
C5 C 0.1768(2) 0.3794(2) 0.18790(14) 0.0261(4) Uani 1 1 d . .
H5 H 0.2499 0.4432 0.1797 0.031 Uiso 1 1 calc R U
C8 C 0.4881(2) 0.8135(2) 0.20280(15) 0.0296(5) Uani 1 1 d . .
C12 C 0.2144(2) 0.7584(2) 0.18599(16) 0.0346(5) Uani 1 1 d . .
H12 H 0.1332 0.7153 0.2033 0.041 Uiso 1 1 calc R U
C14 C 0.5412(2) 0.67156(19) 0.33714(14) 0.0254(4) Uani 1 1 d . .
C7 C 0.0213(2) 0.1561(2) 0.12671(15) 0.0281(4) Uani 1 1 d . .
H7 H -0.0117 0.0675 0.0765 0.034 Uiso 1 1 calc R U
C13 C 0.3668(2) 0.7492(2) 0.23130(15) 0.0276(4) Uani 1 1 d . .
C6 C 0.1290(2) 0.2492(2) 0.11506(14) 0.0259(4) Uani 1 1 d . .
C3 C 0.0092(2) 0.3228(2) 0.28473(15) 0.0299(5) Uani 1 1 d . .
H3 H -0.0319 0.3483 0.3427 0.036 Uiso 1 1 calc R U
C2 C -0.0381(2) 0.1928(2) 0.21173(15) 0.0287(4) Uani 1 1 d . .
C18 C 0.8141(2) 0.7212(2) 0.35086(16) 0.0350(5) Uani 1 1 d . .
H18 H 0.8955 0.7629 0.3329 0.042 Uiso 1 1 calc R U
C17 C 0.8433(2) 0.6487(2) 0.41695(17) 0.0370(5) Uani 1 1 d . .
H17 H 0.9454 0.6392 0.4441 0.044 Uiso 1 1 calc R U
C4 C 0.1170(2) 0.4158(2) 0.27290(15) 0.0267(4) Uani 1 1 d . .
C10 C 0.3039(3) 0.8945(2) 0.09166(17) 0.0406(5) Uani 1 1 d . .
H10 H 0.2805 0.9453 0.0455 0.049 Uiso 1 1 calc R U
C9 C 0.4502(3) 0.8859(2) 0.13104(16) 0.0370(5) Uani 1 1 d . .
H9 H 0.5285 0.9284 0.1109 0.044 Uiso 1 1 calc R U
C16 C 0.7245(2) 0.5867(2) 0.44651(16) 0.0359(5) Uani 1 1 d . .
H16 H 0.7477 0.5374 0.4936 0.043 Uiso 1 1 calc R U
C11 C 0.1847(3) 0.8284(2) 0.11836(17) 0.0393(5) Uani 1 1 d . .
H11 H 0.0827 0.8332 0.0884 0.047 Uiso 1 1 calc R U
C1 C -0.1504(3) 0.0869(2) 0.22415(18) 0.0406(6) Uani 1 1 d . .
H1A H -0.1159 0.0708 0.2879 0.061 Uiso 1 1 calc R U
H1B H -0.1582 -0.0034 0.1705 0.061 Uiso 1 1 calc R U
H1C H -0.2498 0.1248 0.2221 0.061 Uiso 1 1 calc R U
N3 N 0.39626(18) 0.41555(17) 0.02092(12) 0.0281(4) Uani 1 1 d . .
C21 C 0.5441(2) 0.4237(2) 0.06185(14) 0.0269(4) Uani 1 1 d . .
C22 C 0.3504(2) 0.4907(2) -0.04037(14) 0.0268(4) Uani 1 1 d . .
C20 C 0.5902(3) 0.3391(2) 0.13139(17) 0.0386(5) Uani 1 1 d . .
H20A H 0.6216 0.4042 0.1992 0.058 Uiso 1 1 calc R U
H20B H 0.6747 0.2843 0.1127 0.058 Uiso 1 1 calc R U
H20C H 0.5043 0.2738 0.1276 0.058 Uiso 1 1 calc R U
C23 C 0.1845(2) 0.4795(3) -0.08341(17) 0.0410(5) Uani 1 1 d . .
H23A H 0.1306 0.4140 -0.0595 0.061 Uiso 1 1 calc R U
H23B H 0.1675 0.4432 -0.1558 0.061 Uiso 1 1 calc R U
H23C H 0.1467 0.5738 -0.0631 0.061 Uiso 1 1 calc R U
C31 C 0.4916(2) 0.0421(2) 0.46769(14) 0.0283(4) Uani 1 1 d . .
C29 C 0.6215(3) 0.1176(2) 0.45866(17) 0.0387(5) Uani 1 1 d . .
C25 C 0.3479(3) 0.0530(2) 0.41313(16) 0.0390(5) Uani 1 1 d . .
C30 C 0.7659(3) 0.1020(3) 0.5139(2) 0.0505(7) Uani 1 1 d . .
H30 H 0.8539 0.1503 0.5078 0.061 Uiso 1 1 calc R U
C24 C 0.2192(3) -0.0224(3) 0.42662(19) 0.0499(7) Uani 1 1 d . .
H24 H 0.1209 -0.0148 0.3919 0.060 Uiso 1 1 calc R U
C28 C 0.6018(4) 0.2028(3) 0.3966(2) 0.0554(8) Uani 1 1 d . .
H28 H 0.6870 0.2562 0.3915 0.066 Uiso 1 1 calc R U
C26 C 0.3358(4) 0.1372(3) 0.35024(18) 0.0574(8) Uani 1 1 d . .
H26 H 0.2399 0.1438 0.3121 0.069 Uiso 1 1 calc R U
C27 C 0.4638(4) 0.2104(3) 0.3438(2) 0.0629(9) Uani 1 1 d . .
H27 H 0.4544 0.2675 0.3012 0.075 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
C13 N1 C14 117.81(16) . .
C4 O1 H1O 109.6(17) . .
C6 O2 H2O 109.6(16) . .
C8 N2 C19 116.94(16) . .
N2 C19 C18 119.96(17) . .
N2 C19 C14 121.80(18) . .
C18 C19 C14 118.22(19) . .
C16 C15 C14 120.54(19) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C6 C5 C4 119.52(17) . .
C6 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
N2 C8 C9 119.97(18) . .
N2 C8 C13 121.61(18) . .
C9 C8 C13 118.41(19) . .
C11 C12 C13 120.32(19) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
N1 C14 C15 120.01(17) . .
N1 C14 C19 120.74(18) . .
C15 C14 C19 119.25(18) . .
C2 C7 C6 120.04(18) . .
C2 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
N1 C13 C12 120.03(17) . .
N1 C13 C8 121.09(18) . .
C12 C13 C8 118.88(18) . .
O2 C6 C5 122.06(16) . .
O2 C6 C7 117.68(17) . .
C5 C6 C7 120.26(17) . .
C2 C3 C4 119.88(18) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C2 C7 119.98(17) . .
C3 C2 C1 121.16(19) . .
C7 C2 C1 118.83(18) . .
C17 C18 C19 120.46(19) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C18 C17 C16 121.3(2) . .
C18 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
O1 C4 C5 121.64(16) . .
O1 C4 C3 118.05(17) . .
C5 C4 C3 120.30(18) . .
C9 C10 C11 120.9(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C9 C8 120.6(2) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C15 C16 C17 120.2(2) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C12 C11 C10 120.9(2) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C22 N3 C21 119.46(16) . .
N3 C21 C22 120.43(18) . 2_665
N3 C21 C20 117.64(17) . .
C22 C21 C20 121.93(19) 2_665 .
N3 C22 C21 120.11(18) . 2_665
N3 C22 C23 117.58(17) . .
C21 C22 C23 122.32(19) 2_665 .
C21 C20 H20A 109.5 . .
C21 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C21 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C25 C31 C31 120.9(2) . 2_656
C25 C31 C29 119.5(2) . .
C31 C31 C29 119.5(2) 2_656 .
C28 C29 C31 118.5(2) . .
C28 C29 C30 123.6(2) . .
C31 C29 C30 117.9(2) . .
C26 C25 C31 119.3(2) . .
C26 C25 C24 123.2(2) . .
C31 C25 C24 117.5(2) . .
C24 C30 C29 122.2(2) 2_656 .
C24 C30 H30 118.9 2_656 .
C29 C30 H30 118.9 . .
C30 C24 C25 121.9(2) 2_656 .
C30 C24 H24 119.1 2_656 .
C25 C24 H24 119.1 . .
C27 C28 C29 121.2(3) . .
C27 C28 H28 119.4 . .
C29 C28 H28 119.4 . .
C27 C26 C25 119.9(3) . .
C27 C26 H26 120.1 . .
C25 C26 H26 120.1 . .
C28 C27 C26 121.5(3) . .
C28 C27 H27 119.2 . .
C26 C27 H27 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C13 1.337(3) .
N1 C14 1.347(2) .
O1 C4 1.369(2) .
O1 H1O 0.97(3) .
O2 C6 1.367(2) .
O2 H2O 0.91(3) .
N2 C8 1.342(3) .
N2 C19 1.344(3) .
C19 C18 1.428(3) .
C19 C14 1.437(3) .
C15 C16 1.360(3) .
C15 C14 1.422(3) .
C15 H15 0.9500 .
C5 C6 1.389(3) .
C5 C4 1.391(3) .
C5 H5 0.9500 .
C8 C9 1.430(3) .
C8 C13 1.440(3) .
C12 C11 1.355(3) .
C12 C13 1.426(3) .
C12 H12 0.9500 .
C7 C2 1.389(3) .
C7 C6 1.391(3) .
C7 H7 0.9500 .
C3 C2 1.388(3) .
C3 C4 1.393(3) .
C3 H3 0.9500 .
C2 C1 1.513(3) .
C18 C17 1.355(3) .
C18 H18 0.9500 .
C17 C16 1.420(3) .
C17 H17 0.9500 .
C10 C9 1.351(3) .
C10 C11 1.420(3) .
C10 H10 0.9500 .
C9 H9 0.9500 .
C16 H16 0.9500 .
C11 H11 0.9500 .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
N3 C22 1.339(3) .
N3 C21 1.343(3) .
C21 C22 1.399(3) 2_665
C21 C20 1.504(3) .
C22 C21 1.399(3) 2_665
C22 C23 1.497(3) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C31 C25 1.411(3) .
C31 C31 1.423(4) 2_656
C31 C29 1.423(3) .
C29 C28 1.401(4) .
C29 C30 1.433(4) .
C25 C26 1.402(4) .
C25 C24 1.442(4) .
C30 C24 1.325(4) 2_656
C30 H30 0.9500 .
C24 C30 1.325(4) 2_656
C24 H24 0.9500 .
C28 C27 1.349(4) .
C28 H28 0.9500 .
C26 C27 1.383(4) .
C26 H26 0.9500 .
C27 H27 0.9500 .
