#------------------------------------------------------------------------------
#$Date: 2017-04-25 08:35:58 +0300 (Tue, 25 Apr 2017) $
#$Revision: 195747 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545839.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_1545839
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            'C38 H52 N6 O4'
_chemical_formula_weight         656.85
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                114.633(8)
_cell_angle_beta                 93.749(7)
_cell_angle_gamma                101.000(7)
_cell_formula_units_Z            1
_cell_length_a                   8.8712(8)
_cell_length_b                   10.1819(9)
_cell_length_c                   11.2862(10)
_cell_measurement_temperature    150(2)
_cell_volume                     897.56(16)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9617
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.127
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       Plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0434
_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)+(0.0580P)²+0.3975P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3555
_reflns_number_total             4113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5641.cif
_cod_data_source_block           BS_ORC_TMP
_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_original_cell_volume        897.56(15)
_cod_database_code               1545839
_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   0.963
_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
C1 C 0.44502(14) 0.50013(14) 0.23039(13) 0.0176(3) Uani 1 1 d . .
C2 C 0.41232(15) 0.54440(14) 0.35846(13) 0.0189(3) Uani 1 1 d . .
H2 H 0.4500 0.5027 0.4122 0.023 Uiso 1 1 calc R U
C3 C 0.32454(15) 0.64961(14) 0.40809(13) 0.0178(3) Uani 1 1 d . .
C4 C 0.27023(14) 0.71307(14) 0.33137(13) 0.0176(3) Uani 1 1 d . .
H4 H 0.2112 0.7854 0.3657 0.021 Uiso 1 1 calc R U
C5 C 0.30368(15) 0.66908(14) 0.20318(13) 0.0176(3) Uani 1 1 d . .
C6 C 0.39006(15) 0.56246(14) 0.15261(13) 0.0182(3) Uani 1 1 d . .
H6 H 0.4114 0.5324 0.0649 0.022 Uiso 1 1 calc R U
C7 C 0.53436(17) 0.38112(15) 0.17558(15) 0.0235(3) Uani 1 1 d . .
H7A H 0.5898 0.3717 0.2485 0.035 Uiso 1 1 calc R U
H7B H 0.6095 0.4086 0.1250 0.035 Uiso 1 1 calc R U
H7C H 0.4617 0.2859 0.1177 0.035 Uiso 1 1 calc R U
C8 C 0.28890(16) -0.06667(16) -0.06807(15) 0.0252(3) Uani 1 1 d . .
H8A H 0.3686 0.0263 -0.0397 0.038 Uiso 1 1 calc R U
H8B H 0.2781 -0.1249 -0.1639 0.038 Uiso 1 1 calc R U
H8C H 0.3197 -0.1242 -0.0234 0.038 Uiso 1 1 calc R U
C9 C 0.13595(15) -0.03159(14) -0.03299(13) 0.0185(3) Uani 1 1 d . .
C10 C 0.00062(15) 0.14434(14) 0.07142(13) 0.0183(3) Uani 1 1 d . .
C11 C 0.00087(17) 0.30556(15) 0.14974(15) 0.0245(3) Uani 1 1 d . .
H11A H 0.1080 0.3663 0.1741 0.037 Uiso 1 1 calc R U
H11B H -0.0437 0.3183 0.2299 0.037 Uiso 1 1 calc R U
H11C H -0.0615 0.3371 0.0962 0.037 Uiso 1 1 calc R U
C12 C -0.05460(15) 0.83295(14) 0.59691(13) 0.0189(3) Uani 1 1 d . .
C13 C -0.14339(15) 0.92883(15) 0.67063(13) 0.0181(3) Uani 1 1 d . .
C14 C 0.07366(15) 1.12628(14) 0.74744(13) 0.0186(3) Uani 1 1 d . .
C15 C 0.16284(15) 1.03029(15) 0.67567(13) 0.0197(3) Uani 1 1 d . .
C16 C -0.12390(17) 0.67050(16) 0.51069(16) 0.0282(3) Uani 1 1 d . .
H16A H -0.0448 0.6249 0.4633 0.042 Uiso 1 1 calc R U
H16B H -0.2117 0.6591 0.4469 0.042 Uiso 1 1 calc R U
H16C H -0.1604 0.6215 0.5656 0.042 Uiso 1 1 calc R U
C17 C -0.31221(16) 0.87402(17) 0.67158(16) 0.0266(3) Uani 1 1 d . .
H17A H -0.3554 0.9587 0.7222 0.040 Uiso 1 1 calc R U
H17B H -0.3234 0.8054 0.7125 0.040 Uiso 1 1 calc R U
H17C H -0.3683 0.8221 0.5807 0.040 Uiso 1 1 calc R U
C18 C 0.14247(18) 1.28915(16) 0.83228(16) 0.0282(3) Uani 1 1 d . .
H18A H 0.0587 1.3414 0.8534 0.042 Uiso 1 1 calc R U
H18B H 0.2110 1.3297 0.7846 0.042 Uiso 1 1 calc R U
H18C H 0.2026 1.3027 0.9142 0.042 Uiso 1 1 calc R U
C19 C 0.33355(17) 1.08352(17) 0.67812(17) 0.0300(3) Uani 1 1 d . .
H19A H 0.3737 0.9999 0.6203 0.045 Uiso 1 1 calc R U
H19B H 0.3891 1.1243 0.7686 0.045 Uiso 1 1 calc R U
H19C H 0.3492 1.1610 0.6471 0.045 Uiso 1 1 calc R U
N1 N 0.09765(13) 0.88507(12) 0.60240(11) 0.0198(2) Uani 1 1 d . .
N2 N -0.07764(13) 1.07368(12) 0.74435(11) 0.0187(2) Uani 1 1 d . .
N3 N 0.13574(13) 0.11187(12) 0.03815(11) 0.0198(2) Uani 1 1 d . .
O1 O 0.29392(12) 0.68723(11) 0.53369(9) 0.0238(2) Uani 1 1 d . .
H1 H 0.2348 0.7458 0.5508 0.036 Uiso 1 1 calc R U
O2 O 0.25516(12) 0.72802(12) 0.12338(10) 0.0254(2) Uani 1 1 d . .
H2A H 0.2019 0.7882 0.1625 0.038 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
C6 C1 C2 119.43(11) . .
C6 C1 C7 120.73(12) . .
C2 C1 C7 119.80(12) . .
C1 C2 C3 120.27(12) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
O1 C3 C4 121.59(11) . .
O1 C3 C2 117.79(12) . .
C4 C3 C2 120.61(12) . .
C3 C4 C5 119.06(12) . .
C3 C4 H4 120.5 . .
C5 C4 H4 120.5 . .
O2 C5 C4 121.96(11) . .
O2 C5 C6 117.56(11) . .
C4 C5 C6 120.48(12) . .
C1 C6 C5 120.13(12) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C1 C7 H7A 109.5 . .
C1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C9 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N3 C9 C10 121.22(12) . 2
N3 C9 C8 117.46(12) . .
C10 C9 C8 121.32(12) 2 .
N3 C10 C9 120.76(12) . 2
N3 C10 C11 117.73(12) . .
C9 C10 C11 121.51(12) 2 .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N1 C12 C13 120.18(12) . .
N1 C12 C16 117.64(12) . .
C13 C12 C16 122.18(12) . .
N2 C13 C12 120.27(12) . .
N2 C13 C17 117.83(12) . .
C12 C13 C17 121.90(12) . .
N2 C14 C15 120.26(12) . .
N2 C14 C18 117.57(12) . .
C15 C14 C18 122.15(12) . .
N1 C15 C14 120.40(12) . .
N1 C15 C19 117.39(12) . .
C14 C15 C19 122.20(12) . .
C12 C16 H16A 109.5 . .
C12 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C12 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 C19 H19A 109.5 . .
C15 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C15 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C15 N1 C12 119.36(11) . .
C13 N2 C14 119.49(11) . .
C10 N3 C9 118.02(11) . .
C3 O1 H1 109.5 . .
C5 O2 H2A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3920(19) .
C1 C2 1.3922(19) .
C1 C7 1.5116(17) .
C2 C3 1.3939(18) .
C2 H2 0.9500 .
C3 O1 1.3665(16) .
C3 C4 1.3893(18) .
C4 C5 1.3959(18) .
C4 H4 0.9500 .
C5 O2 1.3620(16) .
C5 C6 1.3963(17) .
C6 H6 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.5042(18) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 N3 1.3423(17) .
C9 C10 1.3997(18) 2
C10 N3 1.3393(17) .
C10 C9 1.3997(18) 2
C10 C11 1.5049(18) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 N1 1.3408(17) .
C12 C13 1.4028(18) .
C12 C16 1.5009(19) .
C13 N2 1.3391(17) .
C13 C17 1.4975(18) .
C14 N2 1.3393(17) .
C14 C15 1.3986(18) .
C14 C18 1.5010(19) .
C15 N1 1.3403(17) .
C15 C19 1.5022(19) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
O1 H1 0.8400 .
O2 H2A 0.8400 .
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
C4 H4 N2 0.95 2.64 3.3369(17) 131.0 2_576
O1 H1 N1 0.84 1.97 2.8114(15) 176.4 .
O2 H2A N2 0.84 1.95 2.7917(15) 179.0 2_576
