#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/58/1545818.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_1545818
loop_
_publ_author_name
'Mir, Niyaz A.'
'Dubey, Ritesh'
'Desiraju, Gautam R.'
_publ_section_title
;
 Four- and five-component molecular solids: crystal engineering strategies
 based on structural inequivalence
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              96
_journal_page_last               101
_journal_paper_doi               10.1107/S2052252515023945
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C46 H48 N4 O4'
_chemical_formula_weight         720.88
_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
_cell_angle_alpha                96.219(17)
_cell_angle_beta                 94.61(2)
_cell_angle_gamma                90.598(13)
_cell_formula_units_Z            1
_cell_length_a                   7.528(11)
_cell_length_b                   8.948(14)
_cell_length_c                   14.11(2)
_cell_measurement_temperature    150(2)
_cell_volume                     942(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8263
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.456
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'Light Green'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0511
_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)+(0.0997P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2970
_reflns_number_total             3646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hi5640.cif
_cod_data_source_block           MRE_TMP_DPE-I_DP
_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               1545818
_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   0.982
_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
H17 H -0.444(3) 1.107(2) 0.5688(14) 0.037(5) Uiso 1 1 d . .
O1 O 0.37218(16) 0.63621(13) 0.60508(8) 0.0309(3) Uani 1 1 d . .
H1 H 0.2793 0.6870 0.6003 0.046 Uiso 1 1 calc R U
O2 O 0.62466(15) 0.25137(14) 0.77458(9) 0.0330(3) Uani 1 1 d . .
H2 H 0.6004 0.1963 0.8165 0.050 Uiso 1 1 calc R U
N1 N 0.53636(18) 0.08253(15) 0.92627(9) 0.0263(3) Uani 1 1 d . .
C1 C 0.4977(2) 0.44128(17) 0.68696(10) 0.0232(4) Uani 1 1 d . .
C2 C 0.3483(2) 0.52653(17) 0.66374(11) 0.0243(4) Uani 1 1 d . .
C6 C 0.4771(2) 0.33145(18) 0.74917(11) 0.0256(4) Uani 1 1 d . .
C3 C 0.1851(2) 0.5011(2) 0.69874(12) 0.0306(4) Uani 1 1 d . .
H3 H 0.0856 0.5602 0.6822 0.037 Uiso 1 1 calc R U
C10 C 0.5637(2) 0.14368(18) 1.01764(12) 0.0252(4) Uani 1 1 d . .
C23 C 0.9672(2) -0.07469(19) 0.97608(12) 0.0287(4) Uani 1 1 d . .
C4 C 0.1681(2) 0.3885(2) 0.75816(13) 0.0343(4) Uani 1 1 d . .
H4 H 0.0559 0.3697 0.7814 0.041 Uiso 1 1 calc R U
C9 C 0.4726(2) -0.05919(18) 0.90782(12) 0.0266(4) Uani 1 1 d . .
C11 C 0.6316(2) 0.30416(19) 1.03581(14) 0.0354(4) Uani 1 1 d . .
H11A H 0.6384 0.3456 0.9747 0.053 Uiso 1 1 calc R U
H11B H 0.7504 0.3072 1.0700 0.053 Uiso 1 1 calc R U
H11C H 0.5501 0.3640 1.0746 0.053 Uiso 1 1 calc R U
C7 C 0.6709(2) 0.4662(2) 0.64450(12) 0.0307(4) Uani 1 1 d . .
H7A H 0.7675 0.4201 0.6813 0.046 Uiso 1 1 calc R U
H7B H 0.6951 0.5744 0.6466 0.046 Uiso 1 1 calc R U
H7C H 0.6630 0.4203 0.5780 0.046 Uiso 1 1 calc R U
C8 C 0.4378(3) -0.1230(2) 0.80494(13) 0.0380(4) Uani 1 1 d . .
H8A H 0.4734 -0.0489 0.7635 0.057 Uiso 1 1 calc R U
H8B H 0.3105 -0.1474 0.7911 0.057 Uiso 1 1 calc R U
H8C H 0.5068 -0.2145 0.7932 0.057 Uiso 1 1 calc R U
C5 C 0.3129(2) 0.3039(2) 0.78373(12) 0.0324(4) Uani 1 1 d . .
H5 H 0.3008 0.2275 0.8246 0.039 Uiso 1 1 calc R U
C22 C 0.9334(3) -0.1943(2) 1.02800(14) 0.0424(5) Uani 1 1 d . .
H22 H 0.9544 -0.1808 1.0957 0.051 Uiso 1 1 calc R U
C20 C 0.8407(3) -0.3572(2) 0.88588(14) 0.0403(5) Uani 1 1 d . .
H20 H 0.7975 -0.4519 0.8554 0.048 Uiso 1 1 calc R U
C18 C 0.9363(3) -0.1024(2) 0.87693(13) 0.0412(5) Uani 1 1 d . .
H18 H 0.9575 -0.0238 0.8388 0.049 Uiso 1 1 calc R U
C19 C 0.8756(3) -0.2408(2) 0.83261(14) 0.0458(5) Uani 1 1 d . .
H19 H 0.8577 -0.2562 0.7648 0.055 Uiso 1 1 calc R U
C21 C 0.8695(3) -0.3332(2) 0.98343(15) 0.0459(5) Uani 1 1 d . .
H21 H 0.8458 -0.4119 1.0210 0.055 Uiso 1 1 calc R U
N2 N 0.06357(19) 0.80524(16) 0.58357(10) 0.0319(4) Uani 1 1 d . .
C14 C -0.2680(2) 0.94290(18) 0.55156(11) 0.0276(4) Uani 1 1 d . .
C12 C 0.0305(2) 0.9421(2) 0.62581(12) 0.0328(4) Uani 1 1 d . .
H12 H 0.1230 0.9934 0.6669 0.039 Uiso 1 1 calc R U
C13 C -0.1302(2) 1.0133(2) 0.61317(12) 0.0316(4) Uani 1 1 d . .
H13 H -0.1470 1.1097 0.6462 0.038 Uiso 1 1 calc R U
C15 C -0.2336(2) 0.8001(2) 0.50744(13) 0.0339(4) Uani 1 1 d . .
H15 H -0.3226 0.7465 0.4651 0.041 Uiso 1 1 calc R U
C17 C -0.4360(2) 1.0211(2) 0.53399(13) 0.0311(4) Uani 1 1 d . .
C16 C -0.0699(2) 0.7375(2) 0.52561(13) 0.0350(4) Uani 1 1 d . .
H16 H -0.0503 0.6398 0.4951 0.042 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
C2 O1 H1 109.5 . .
C6 O2 H2 109.5 . .
C9 N1 C10 119.06(14) . .
C6 C1 C2 117.42(16) . .
C6 C1 C7 122.04(15) . .
C2 C1 C7 120.53(17) . .
O1 C2 C3 121.86(15) . .
O1 C2 C1 116.61(16) . .
C3 C2 C1 121.53(17) . .
O2 C6 C5 121.11(16) . .
O2 C6 C1 117.53(15) . .
C5 C6 C1 121.36(15) . .
C2 C3 C4 119.55(16) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
N1 C10 C9 120.04(18) . 2_657
N1 C10 C11 117.73(15) . .
C9 C10 C11 122.22(17) 2_657 .
C22 C23 C18 116.31(18) . .
C22 C23 C23 121.8(2) . 2_757
C18 C23 C23 121.85(19) . 2_757
C5 C4 C3 120.53(17) . .
C5 C4 H4 119.7 . .
C3 C4 H4 119.7 . .
N1 C9 C10 120.89(16) . 2_657
N1 C9 C8 117.93(15) . .
C10 C9 C8 121.17(18) 2_657 .
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 . .
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 . .
C4 C5 C6 119.56(17) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C21 C22 C23 121.8(2) . .
C21 C22 H22 119.1 . .
C23 C22 H22 119.1 . .
C21 C20 C19 118.71(19) . .
C21 C20 H20 120.6 . .
C19 C20 H20 120.6 . .
C19 C18 C23 121.85(18) . .
C19 C18 H18 119.1 . .
C23 C18 H18 119.1 . .
C18 C19 C20 120.7(2) . .
C18 C19 H19 119.6 . .
C20 C19 H19 119.6 . .
C20 C21 C22 120.56(19) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C12 N2 C16 116.13(16) . .
C15 C14 C13 116.47(17) . .
C15 C14 C17 123.51(16) . .
C13 C14 C17 120.00(18) . .
N2 C12 C13 123.85(16) . .
N2 C12 H12 118.1 . .
C13 C12 H12 118.1 . .
C12 C13 C14 119.71(18) . .
C12 C13 H13 120.1 . .
C14 C13 H13 120.1 . .
C16 C15 C14 119.57(17) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C17 C17 C14 125.9(2) 2_476 .
C17 C17 H17 119.0(13) 2_476 .
C14 C17 H17 114.9(13) . .
N2 C16 C15 124.26(18) . .
N2 C16 H16 117.9 . .
C15 C16 H16 117.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.370(2) .
O1 H1 0.8400 .
O2 C6 1.373(2) .
O2 H2 0.8400 .
N1 C9 1.342(3) .
N1 C10 1.344(3) .
C1 C6 1.402(3) .
C1 C2 1.403(3) .
C1 C7 1.502(3) .
C2 C3 1.386(3) .
C6 C5 1.394(3) .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C10 C9 1.402(3) 2_657
C10 C11 1.508(3) .
C23 C22 1.394(3) .
C23 C18 1.395(3) .
C23 C23 1.491(4) 2_757
C4 C5 1.380(3) .
C4 H4 0.9500 .
C9 C10 1.402(3) 2_657
C9 C8 1.503(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C5 H5 0.9500 .
C22 C21 1.392(3) .
C22 H22 0.9500 .
C20 C21 1.369(3) .
C20 C19 1.384(3) .
C20 H20 0.9500 .
C18 C19 1.381(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C21 H21 0.9500 .
N2 C12 1.338(3) .
N2 C16 1.340(3) .
C14 C15 1.395(3) .
C14 C13 1.397(3) .
C14 C17 1.468(3) .
C12 C13 1.381(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C15 C16 1.376(3) .
C15 H15 0.9500 .
C17 C17 1.326(4) 2_476
C17 H17 0.87(2) .
C16 H16 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
C5 H5 N1 0.95 2.63 3.345(4) 132.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049926
