#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/52/1545209.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1545209
loop_
_publ_author_name
'Patil, Pravin'
'Madhavachary, Rudrakshula'
'Kurpiewska, Katarzyna'
'Kalinowska-Tłuścik, Justyna'
'Dömling, Alexander'
_publ_section_title
;
 De Novo Assembly of Highly Substituted Morpholines and Piperazines.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              642
_journal_page_last               645
_journal_paper_doi               10.1021/acs.orglett.6b03807
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H25 N5 O'
_chemical_formula_sum            'C13 H25 N5 O'
_chemical_formula_weight         267.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-28T09:22:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                72.849(11)
_cell_angle_beta                 74.617(11)
_cell_angle_gamma                74.654(11)
_cell_formula_units_Z            2
_cell_length_a                   7.8022(10)
_cell_length_b                   9.7161(12)
_cell_length_c                   10.8980(13)
_cell_measurement_reflns_used    3335
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      27.5310
_cell_measurement_theta_min      3.0550
_cell_volume                     745.38(17)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10330
_diffrn_reflns_theta_full        26.3154
_diffrn_reflns_theta_max         28.6452
_diffrn_reflns_theta_min         3.0647
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                2364
_reflns_number_total             3847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03807_si_005.cif
_cod_data_source_block           mcr141_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        745.38(16)
_cod_database_code               1545209
#BEGIN Tags that were not found in dictionaries:
_cell_oxdiff_length_a            7.8022(10)
_cell_oxdiff_length_b            9.7161(12)
_cell_oxdiff_length_c            10.8980(13)
_cell_oxdiff_angle_alpha         72.849(11)
_cell_oxdiff_angle_beta          74.617(11)
_cell_oxdiff_angle_gamma         74.654(11)
_cell_oxdiff_volume              745.38(15)
_cell_oxdiff_measurement_reflns_used 3335
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_refinement_flags
O10 O 0.14336(17) 0.85629(13) 0.21574(12) 0.0339(3) Uani 1 d .
N1 N 0.46016(18) 0.35280(14) 0.38229(12) 0.0197(3) Uani 1 d .
N7 N 0.10625(19) 0.55895(15) 0.25028(13) 0.0219(3) Uani 1 d .
N4 N 0.25306(19) 0.46592(15) 0.51761(12) 0.0259(4) Uani 1 d .
N2 N 0.47012(19) 0.27098(15) 0.50611(12) 0.0248(4) Uani 1 d .
N3 N 0.3465(2) 0.33977(16) 0.58573(13) 0.0282(4) Uani 1 d .
C16 C 0.3827(2) 0.17273(17) 0.19305(14) 0.0217(4) Uani 1 d .
C15 C 0.4884(2) 0.29637(17) 0.16784(14) 0.0209(4) Uani 1 d .
H15A H 0.5755 0.294 0.086 0.025 Uiso 1 calc R
H15B H 0.402 0.3888 0.1523 0.025 Uiso 1 calc R
C8 C 0.0291(2) 0.68345(19) 0.15233(15) 0.0270(4) Uani 1 d .
H8A H -0.082 0.6654 0.1417 0.032 Uiso 1 calc R
H8B H 0.1138 0.6892 0.0687 0.032 Uiso 1 calc R
C9 C -0.0123(2) 0.82994(18) 0.18826(16) 0.0281(4) Uani 1 d .
H9A H -0.0518 0.9083 0.1163 0.034 Uiso 1 calc R
H9B H -0.1104 0.8303 0.2646 0.034 Uiso 1 calc R
C12 C 0.5927(2) 0.30452(18) 0.26698(14) 0.0212(4) Uani 1 d .
C5 C 0.3253(2) 0.47240(18) 0.39199(15) 0.0203(4) Uani 1 d .
C6 C 0.2568(2) 0.59539(17) 0.28426(15) 0.0211(4) Uani 1 d .
H7 H 0.3557 0.6025 0.2068 0.025 Uiso 1 calc R
C18 C 0.2631(2) 0.22595(19) 0.08891(16) 0.0294(4) Uani 1 d .
H18A H 0.3388 0.2428 0.0029 0.044 Uiso 1 calc R
H18B H 0.1801 0.3158 0.1009 0.044 Uiso 1 calc R
H18C H 0.1961 0.1524 0.0983 0.044 Uiso 1 calc R
C14 C 0.7166(2) 0.16002(19) 0.31846(16) 0.0293(4) Uani 1 d .
H14A H 0.7855 0.1756 0.3724 0.044 Uiso 1 calc R
H14B H 0.7978 0.1249 0.2459 0.044 Uiso 1 calc R
H14C H 0.6444 0.0885 0.3694 0.044 Uiso 1 calc R
C11 C 0.2031(3) 0.74227(19) 0.32230(17) 0.0318(5) Uani 1 d .
H11A H 0.1064 0.7381 0.3997 0.038 Uiso 1 calc R
H11B H 0.3063 0.7628 0.3425 0.038 Uiso 1 calc R
C17 C 0.2571(3) 0.1476(2) 0.32893(15) 0.0291(4) Uani 1 d .
H17A H 0.1888 0.0754 0.3367 0.044 Uiso 1 calc R
H17B H 0.1753 0.2383 0.3397 0.044 Uiso 1 calc R
H17C H 0.3287 0.1133 0.3954 0.044 Uiso 1 calc R
C19 C 0.5085(2) 0.02780(18) 0.17147(16) 0.0294(4) Uani 1 d .
H19A H 0.5699 -0.0173 0.2434 0.044 Uiso 1 calc R
H19B H 0.5962 0.0468 0.0912 0.044 Uiso 1 calc R
H19C H 0.4382 -0.0371 0.1663 0.044 Uiso 1 calc R
C13 C 0.7100(2) 0.4221(2) 0.20314(16) 0.0292(4) Uani 1 d .
H13A H 0.6365 0.5125 0.1644 0.044 Uiso 1 calc R
H13B H 0.8073 0.3893 0.1365 0.044 Uiso 1 calc R
H13C H 0.7592 0.4378 0.2687 0.044 Uiso 1 calc R
H7A H 0.019(3) 0.5428(19) 0.3227(17) 0.034(5) Uiso 1 d .
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 0 '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 0.006 '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
C9 O10 C11 110.27(12)
C5 N1 N2 107.52(13)
C5 N1 C12 132.66(12)
N2 N1 C12 119.77(13)
C8 N7 C6 109.59(13)
C5 N4 N3 106.00(14)
N3 N2 N1 107.00(13)
N2 N3 N4 110.68(12)
C19 C16 C17 110.31(13)
C19 C16 C18 107.14(13)
C17 C16 C18 107.96(14)
C19 C16 C15 112.40(14)
C17 C16 C15 113.06(13)
C18 C16 C15 105.59(12)
C12 C15 C16 122.81(12)
N7 C8 C9 113.49(12)
O10 C9 C8 111.16(14)
N1 C12 C14 108.35(12)
N1 C12 C13 106.55(12)
C14 C12 C13 107.94(13)
N1 C12 C15 109.72(12)
C14 C12 C15 114.13(13)
C13 C12 C15 109.86(12)
N4 C5 N1 108.80(13)
N4 C5 C6 122.33(15)
N1 C5 C6 128.85(14)
N7 C6 C5 109.20(12)
N7 C6 C11 112.46(14)
C5 C6 C11 111.29(12)
O10 C11 C6 109.28(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O10 C9 1.4259(18)
O10 C11 1.4313(19)
N1 C5 1.354(2)
N1 N2 1.3598(16)
N1 C12 1.507(2)
N7 C8 1.4694(19)
N7 C6 1.4735(19)
N4 C5 1.325(2)
N4 N3 1.3646(18)
N2 N3 1.299(2)
C16 C19 1.531(2)
C16 C17 1.535(2)
C16 C18 1.545(2)
C16 C15 1.552(2)
C15 C12 1.5452(19)
C8 C9 1.517(2)
C12 C14 1.525(2)
C12 C13 1.540(2)
C5 C6 1.503(2)
C6 C11 1.525(2)
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
C5 N1 N2 N3 -0.18(16)
C12 N1 N2 N3 177.53(12)
N1 N2 N3 N4 0.29(16)
C5 N4 N3 N2 -0.30(17)
C19 C16 C15 C12 -76.94(19)
C17 C16 C15 C12 48.8(2)
C18 C16 C15 C12 166.58(15)
C6 N7 C8 C9 -49.00(19)
C11 O10 C9 C8 -59.45(18)
N7 C8 C9 O10 53.73(19)
C5 N1 C12 C14 178.62(15)
N2 N1 C12 C14 1.59(17)
C5 N1 C12 C13 62.70(19)
N2 N1 C12 C13 -114.33(15)
C5 N1 C12 C15 -56.2(2)
N2 N1 C12 C15 126.80(14)
C16 C15 C12 N1 -73.31(19)
C16 C15 C12 C14 48.5(2)
C16 C15 C12 C13 169.87(15)
N3 N4 C5 N1 0.18(16)
N3 N4 C5 C6 178.95(13)
N2 N1 C5 N4 -0.01(16)
C12 N1 C5 N4 -177.30(14)
N2 N1 C5 C6 -178.68(14)
C12 N1 C5 C6 4.0(3)
C8 N7 C6 C5 175.61(13)
C8 N7 C6 C11 51.56(18)
N4 C5 C6 N7 -86.82(17)
N1 C5 C6 N7 91.69(19)
N4 C5 C6 C11 37.9(2)
N1 C5 C6 C11 -143.58(15)
C9 O10 C11 C6 61.54(18)
N7 C6 C11 O10 -58.59(18)
C5 C6 C11 O10 178.53(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049568
