Synthesis of morpholine derivatives from 1,3-dienes and <i>N</i>-arylaminoalcohols by palladium-catalyzed sequential C-N and C-O bond formation.
Yamaguchi, Ayumi; Katayama, Nobuki; Tabaru, Kazuki; Fujihara, Tetsuaki; Obora, Yasushi; Organic & biomolecular chemistry 24 (2026) 592–596; doi:10.1039/d5ob01744k

data_7161040
_publ_section_title
;
 Synthesis of morpholine derivatives from 1,3-dienes and
 <i>N</i>-arylaminoalcohols by palladium-catalyzed sequential C-N and C-O
 bond formation.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              592
_journal_page_last               596
_journal_paper_doi               10.1039/d5ob01744k
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '2(C14 H18 N2 O3)'
_chemical_formula_sum            'C28 H36 N4 O6'
_chemical_formula_weight         524.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
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2025-10-30 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
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_cell_length_c                   16.994(4)
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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_computing_data_collection
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
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;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9794
	          2theta: -20.0418
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9794
	          2theta: -20.0418
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724'
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_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0676
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_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       Prism
_exptl_crystal_F_000             560
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
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_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.202
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5759
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_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0357
_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/[\s^2^(Fo^2^)+(0.0373P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0841
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_reflns_number_gt                3358
_reflns_number_total             5759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01744k2.cif
_cod_data_source_block           obora-yamaguchi221108a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1322.2(5)
_cod_database_code               7161040
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H6A,H6B} of C6, {H8A,H8B} of C8, {H20A,H20B} of C20, {H7A,
  H7B} of C7, {H22A,H22B} of C22, {H21A,H21B} of C21
 At 1.5 times of:
  All C(H,H,H) groups, {H4A,H4B} of C4
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C26(H26), C27(H27), C24(H24), C10(H10), C11(H11), C25(H25)
;
_shelx_res_checksum              60009
_olex2_submission_special_instructions 'No special instructions were received'