#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/32/4033266.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_4033266
loop_
_publ_author_name
'Periasamy, Mariappan'
'Mohan, Lakavathu'
'Satyanarayana, Iddum'
'Reddy, Polimera Obula'
_publ_section_title
;
 Enantioselective Synthesis of β-Allenoates via Phosphine Catalysed and
 ZnI2 Promoted Preparation of Oxozolidines and Propargylamines using
 Chiral Amines, 1-Alkynes and Propiolates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02632
_journal_year                    2017
_chemical_absolute_configuration S
_chemical_formula_moiety         'C22 H25 N O3'
_chemical_formula_sum            'C22 H25 N O3'
_chemical_formula_weight         351.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.474(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1961(6)
_cell_length_b                   6.5619(3)
_cell_length_c                   12.9957(8)
_cell_measurement_reflns_used    5277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.65
_cell_volume                     938.86(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10684
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.445
_diffrn_reflns_theta_min         2.652
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0377
_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)+(0.0335P)²+0.1781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3565
_reflns_number_total             3996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02632_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4033266
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.25127(19) 0.6234(3) 0.22469(17) 0.0163(5) Uani 1 1 d . .
C2 C 0.31821(19) 0.7933(3) 0.26417(17) 0.0200(5) Uani 1 1 d . .
H2 H 0.2948 0.8689 0.3196 0.024 Uiso 1 1 calc R U
C3 C 0.4191(2) 0.8540(4) 0.22332(19) 0.0264(5) Uani 1 1 d . .
H3 H 0.4644 0.9699 0.2514 0.032 Uiso 1 1 calc R U
C4 C 0.4539(2) 0.7473(4) 0.14247(19) 0.0263(5) Uani 1 1 d . .
H4 H 0.5235 0.7882 0.1154 0.032 Uiso 1 1 calc R U
C5 C 0.3869(2) 0.5802(4) 0.10098(19) 0.0257(5) Uani 1 1 d . .
H5 H 0.4097 0.5072 0.0444 0.031 Uiso 1 1 calc R U
C005 C 0.14366(19) 0.5470(3) 0.27370(17) 0.0156(4) Uani 1 1 d . .
C6 C 0.2864(2) 0.5187(4) 0.14168(17) 0.0208(5) Uani 1 1 d . .
H6 H 0.2408 0.4037 0.1126 0.025 Uiso 1 1 calc R U
C7 C 0.02868(19) 0.5416(4) 0.18906(17) 0.0184(5) Uani 1 1 d . .
C8 C 0.0035(2) 0.3803(4) 0.11877(19) 0.0254(5) Uani 1 1 d . .
H8 H 0.0570 0.2668 0.1248 0.030 Uiso 1 1 calc R U
C9 C -0.0986(2) 0.3830(4) 0.03990(19) 0.0297(6) Uani 1 1 d . .
H9 H -0.1138 0.2724 -0.0079 0.036 Uiso 1 1 calc R U
C10 C -0.1779(2) 0.5457(4) 0.03067(19) 0.0312(6) Uani 1 1 d . .
H10 H -0.2481 0.5471 -0.0229 0.037 Uiso 1 1 calc R U
C11 C -0.1545(2) 0.7061(4) 0.09993(18) 0.0286(6) Uani 1 1 d . .
H11 H -0.2088 0.8185 0.0938 0.034 Uiso 1 1 calc R U
C12 C -0.05170(19) 0.7050(4) 0.17895(17) 0.0225(5) Uani 1 1 d . .
H12 H -0.0366 0.8166 0.2261 0.027 Uiso 1 1 calc R U
C13 C 0.16984(18) 0.3310(3) 0.32169(16) 0.0169(5) Uani 1 1 d . .
H13 H 0.1797 0.2325 0.2651 0.020 Uiso 1 1 calc R U
C14 C 0.0704(2) 0.2531(4) 0.37977(19) 0.0232(5) Uani 1 1 d . .
H14A H -0.0078 0.3227 0.3539 0.028 Uiso 1 1 calc R U
H14B H 0.0586 0.1044 0.3698 0.028 Uiso 1 1 calc R U
C15 C 0.1165(2) 0.3034(4) 0.49521(18) 0.0250(5) Uani 1 1 d . .
H15A H 0.0962 0.4454 0.5112 0.030 Uiso 1 1 calc R U
H15B H 0.0814 0.2096 0.5414 0.030 Uiso 1 1 calc R U
C16 C 0.2528(2) 0.2747(4) 0.50785(17) 0.0214(5) Uani 1 1 d . .
H16A H 0.2964 0.3670 0.5622 0.026 Uiso 1 1 calc R U
H16B H 0.2760 0.1322 0.5271 0.026 Uiso 1 1 calc R U
C17 C 0.39179(18) 0.3154(3) 0.38308(16) 0.0160(4) Uani 1 1 d . .
H17 H 0.3989 0.3357 0.3121 0.019 Uiso 1 1 calc R U
C18 C 0.4966(2) 0.2796(3) 0.45124(17) 0.0181(5) Uani 1 1 d . .
H18 H 0.4942 0.2503 0.5224 0.022 Uiso 1 1 calc R U
C19 C 0.6112(2) 0.2859(3) 0.41624(17) 0.0184(5) Uani 1 1 d . .
C20 C 0.7111(2) 0.3471(4) 0.2716(2) 0.0305(6) Uani 1 1 d . .
H20A H 0.7782 0.3956 0.3265 0.037 Uiso 1 1 calc R U
H20B H 0.7002 0.4467 0.2135 0.037 Uiso 1 1 calc R U
C21 C 0.7435(3) 0.1442(5) 0.2325(2) 0.0390(7) Uani 1 1 d . .
H21A H 0.8186 0.1564 0.2041 0.059 Uiso 1 1 calc R U
H21B H 0.7556 0.0460 0.2902 0.059 Uiso 1 1 calc R U
H21C H 0.6777 0.0971 0.1773 0.059 Uiso 1 1 calc R U
N1 N 0.27955(16) 0.3254(3) 0.40467(14) 0.0172(4) Uani 1 1 d . .
O1 O 0.11953(13) 0.6837(2) 0.35170(11) 0.0163(3) Uani 1 1 d . .
H1 H 0.1806 0.6910 0.3998 0.024 Uiso 1 1 calc R U
O2 O 0.71118(14) 0.2538(2) 0.47047(13) 0.0240(4) Uani 1 1 d . .
O3 O 0.60083(14) 0.3357(3) 0.31408(13) 0.0292(4) Uani 1 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 0.0000 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
C2 C1 C6 118.2(2)
C2 C1 C005 121.13(19)
C6 C1 C005 120.64(19)
C1 C2 C3 120.7(2)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 120.5(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.5(2)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
O1 C005 C7 106.48(16)
O1 C005 C1 110.75(17)
C7 C005 C1 109.12(17)
O1 C005 C13 109.69(17)
C7 C005 C13 109.80(17)
C1 C005 C13 110.90(17)
C5 C6 C1 120.9(2)
C5 C6 H6 119.5
C1 C6 H6 119.5
C12 C7 C8 118.3(2)
C12 C7 C005 119.61(19)
C8 C7 C005 122.1(2)
C9 C8 C7 121.0(2)
C9 C8 H8 119.5
C7 C8 H8 119.5
C10 C9 C8 120.3(2)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 119.4(2)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C12 120.7(2)
C10 C11 H11 119.7
C12 C11 H11 119.7
C7 C12 C11 120.4(2)
C7 C12 H12 119.8
C11 C12 H12 119.8
N1 C13 C14 102.29(17)
N1 C13 C005 112.68(17)
C14 C13 C005 113.46(18)
N1 C13 H13 109.4
C14 C13 H13 109.4
C005 C13 H13 109.4
C15 C14 C13 105.25(17)
C15 C14 H14A 110.7
C13 C14 H14A 110.7
C15 C14 H14B 110.7
C13 C14 H14B 110.7
H14A C14 H14B 108.8
C16 C15 C14 103.48(19)
C16 C15 H15A 111.1
C14 C15 H15A 111.1
C16 C15 H15B 111.1
C14 C15 H15B 111.1
H15A C15 H15B 109.0
N1 C16 C15 103.99(17)
N1 C16 H16A 111.0
C15 C16 H16A 111.0
N1 C16 H16B 111.0
C15 C16 H16B 111.0
H16A C16 H16B 109.0
N1 C17 C18 127.3(2)
N1 C17 H17 116.4
C18 C17 H17 116.4
C17 C18 C19 120.3(2)
C17 C18 H18 119.9
C19 C18 H18 119.9
O2 C19 O3 120.7(2)
O2 C19 C18 125.9(2)
O3 C19 C18 113.31(17)
O3 C20 C21 111.2(2)
O3 C20 H20A 109.4
C21 C20 H20A 109.4
O3 C20 H20B 109.4
C21 C20 H20B 109.4
H20A C20 H20B 108.0
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C17 N1 C16 122.49(17)
C17 N1 C13 122.35(18)
C16 N1 C13 113.06(17)
C005 O1 H1 109.5
C19 O3 C20 117.50(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.389(3)
C1 C6 1.394(3)
C1 C005 1.545(3)
C2 C3 1.391(3)
C2 H2 0.9500
C3 C4 1.376(4)
C3 H3 0.9500
C4 C5 1.381(4)
C4 H4 0.9500
C5 C6 1.388(3)
C5 H5 0.9500
C005 O1 1.416(3)
C005 C7 1.534(3)
C005 C13 1.555(3)
C6 H6 0.9500
C7 C12 1.391(3)
C7 C8 1.393(3)
C8 C9 1.390(3)
C8 H8 0.9500
C9 C10 1.380(4)
C9 H9 0.9500
C10 C11 1.379(4)
C10 H10 0.9500
C11 C12 1.396(3)
C11 H11 0.9500
C12 H12 0.9500
C13 N1 1.480(3)
C13 C14 1.542(3)
C13 H13 1.0000
C14 C15 1.531(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.516(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N1 1.465(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 N1 1.338(3)
C17 C18 1.356(3)
C17 H17 0.9500
C18 C19 1.438(3)
C18 H18 0.9500
C19 O2 1.228(3)
C19 O3 1.352(3)
C20 O3 1.442(3)
C20 C21 1.494(4)
C20 H20A 0.9900
C20 H20B 0.9900
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
O1 H1 0.8400
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095804
