#------------------------------------------------------------------------------
#$Date: 2020-04-07 02:26:48 +0300 (Tue, 07 Apr 2020) $
#$Revision: 250421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038193.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_4038193
loop_
_publ_author_name
'Zhang, Yue'
'Li, Jun-Kuan'
'Zhang, Fa-Guang'
'Ma, Jun-An'
_publ_section_title
;
 Catalytic Asymmetric Access to Noncanonical Chiral α-Amino Acids from
 Cyclic Iminoglyoxylates and Enamides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00436
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H24 N2 O3'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4501(3)
_cell_length_b                   9.7777(3)
_cell_length_c                   23.5886(8)
_cell_measurement_reflns_used    9305
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.467
_cell_measurement_theta_min      4.895
_cell_volume                     2179.59(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23098
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         4.896
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1636 before and 0.0838 after correction. The Ratio of minimum to maximum transmission is 0.7619. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0430
_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)+(0.0682P)²+0.5872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4070
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00436_si_004.cif
_cod_data_source_block           zz
_cod_database_code               4038193
_shelx_shelxl_version_number     2018/3
_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_max   0.974
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N28(H28), C5(H5), C17(H17), C20(H20), C13(H13), C3(H3), C4(H4), C9(H9),
 C1(H1), C2(H2), C12(H12), C10(H10), C21(H21), C24(H24), C11(H11), C22(H22),
 C23(H23)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.8310(2) 0.2433(2) 0.52720(8) 0.0455(5) Uani 1 1 d . . . . .
O3 O 0.91674(19) 0.7160(2) 0.50967(10) 0.0472(5) Uani 1 1 d . . . . .
O1 O 0.6728(2) 0.0894(2) 0.54818(9) 0.0450(5) Uani 1 1 d . . . . .
N27 N 0.4757(2) 0.2910(2) 0.58449(9) 0.0308(4) Uani 1 1 d . . . . .
N28 N 0.6818(2) 0.6896(2) 0.51856(9) 0.0338(5) Uani 1 1 d . . . . .
H28 H 0.597343 0.722189 0.510536 0.041 Uiso 1 1 calc R . . . .
C15 C 0.7143(3) 0.2191(3) 0.54620(10) 0.0357(5) Uani 1 1 d . . . . .
C18 C 0.6923(3) 0.5709(3) 0.55357(10) 0.0311(5) Uani 1 1 d . . . . .
C16 C 0.6226(3) 0.3294(3) 0.57271(10) 0.0310(5) Uani 1 1 d . . . . .
H16 H 0.666589 0.352311 0.610069 0.037 Uiso 1 1 calc R . . . .
C25 C 0.7958(3) 0.7532(3) 0.49748(12) 0.0339(5) Uani 1 1 d . . . . .
C19 C 0.7692(3) 0.5855(3) 0.60844(11) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.4666(3) 0.1512(2) 0.60790(10) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.5443(3) 0.1496(3) 0.66497(11) 0.0331(5) Uani 1 1 d . . . . .
C5 C 0.2718(3) -0.0244(3) 0.62212(12) 0.0413(6) Uani 1 1 d . . . . .
H5 H 0.342967 -0.093025 0.622016 0.050 Uiso 1 1 calc R . . . .
C6 C 0.3105(3) 0.1119(3) 0.61634(10) 0.0333(5) Uani 1 1 d . . . . .
C17 C 0.6286(3) 0.4573(3) 0.53753(11) 0.0333(5) Uani 1 1 d . . . . .
H17 H 0.583701 0.456294 0.501496 0.040 Uiso 1 1 calc R . . . .
C14 C 0.5299(3) 0.0536(3) 0.56411(12) 0.0389(6) Uani 1 1 d . . . . .
H14A H 0.529532 -0.040316 0.579787 0.047 Uiso 1 1 calc R . . . .
H14B H 0.469543 0.053849 0.529813 0.047 Uiso 1 1 calc R . . . .
C26 C 0.7681(3) 0.8684(3) 0.45684(12) 0.0387(6) Uani 1 1 d . . . . .
H26A H 0.801934 0.954381 0.473302 0.058 Uiso 1 1 calc GR . . . .
H26B H 0.666212 0.875023 0.449549 0.058 Uiso 1 1 calc GR . . . .
H26C H 0.817960 0.850848 0.421151 0.058 Uiso 1 1 calc GR . . . .
C20 C 0.9002(3) 0.5245(3) 0.61697(13) 0.0434(6) Uani 1 1 d . . . . .
H20 H 0.944062 0.476093 0.586808 0.052 Uiso 1 1 calc R . . . .
C13 C 0.6279(3) 0.0425(3) 0.68260(14) 0.0458(7) Uani 1 1 d . . . . .
H13 H 0.638737 -0.035441 0.658934 0.055 Uiso 1 1 calc R . . . .
C3 C 0.0281(3) 0.0362(4) 0.62897(13) 0.0492(7) Uani 1 1 d . . . . .
H3 H -0.068455 0.010500 0.632368 0.059 Uiso 1 1 calc R . . . .
C4 C 0.1307(3) -0.0622(3) 0.62806(13) 0.0486(7) Uani 1 1 d . . . . .
H4 H 0.105831 -0.155938 0.631466 0.058 Uiso 1 1 calc R . . . .
C9 C 0.5331(3) 0.2644(3) 0.70014(11) 0.0461(7) Uani 1 1 d . . . . .
H9 H 0.475767 0.339209 0.688567 0.055 Uiso 1 1 calc R . . . .
C1 C 0.2048(3) 0.2097(3) 0.61836(13) 0.0428(6) Uani 1 1 d . . . . .
H1 H 0.228375 0.303810 0.615187 0.051 Uiso 1 1 calc R . . . .
C2 C 0.0635(3) 0.1707(4) 0.62504(14) 0.0505(7) Uani 1 1 d . . . . .
H2 H -0.008318 0.238527 0.626850 0.061 Uiso 1 1 calc R . . . .
C12 C 0.6969(4) 0.0470(4) 0.73486(16) 0.0584(9) Uani 1 1 d . . . . .
H12 H 0.752551 -0.028503 0.746932 0.070 Uiso 1 1 calc R . . . .
C10 C 0.6039(4) 0.2711(5) 0.75148(13) 0.0594(9) Uani 1 1 d . . . . .
H10 H 0.596960 0.350670 0.774393 0.071 Uiso 1 1 calc R . . . .
C21 C 0.9676(4) 0.5336(4) 0.66895(15) 0.0561(8) Uani 1 1 d . . . . .
H21 H 1.056970 0.490915 0.674229 0.067 Uiso 1 1 calc R . . . .
C24 C 0.7081(4) 0.6545(4) 0.65277(15) 0.0613(9) Uani 1 1 d . . . . .
H24 H 0.618867 0.697477 0.647607 0.074 Uiso 1 1 calc R . . . .
C11 C 0.6845(4) 0.1613(4) 0.76916(14) 0.0601(9) Uani 1 1 d . . . . .
H11 H 0.731381 0.164177 0.804772 0.072 Uiso 1 1 calc R . . . .
C22 C 0.9066(5) 0.6035(4) 0.71264(15) 0.0671(10) Uani 1 1 d . . . . .
H22 H 0.954406 0.611358 0.747914 0.081 Uiso 1 1 calc R . . . .
C23 C 0.7756(6) 0.6625(5) 0.70550(17) 0.0788(13) Uani 1 1 d . . . . .
H23 H 0.731142 0.708425 0.736201 0.095 Uiso 1 1 calc R . . . .
H27 H 0.428(3) 0.295(3) 0.5518(13) 0.032(7) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C15 O1 C14 121.1(2) . . ?
C16 N27 C7 111.29(19) . . ?
C16 N27 H27 107.9(19) . . ?
C7 N27 H27 109(2) . . ?
C18 N28 H28 118.8 . . ?
C25 N28 H28 118.8 . . ?
C25 N28 C18 122.4(2) . . ?
O2 C15 O1 117.9(3) . . ?
O2 C15 C16 122.1(3) . . ?
O1 C15 C16 119.6(2) . . ?
N28 C18 C19 117.3(2) . . ?
C17 C18 N28 119.1(2) . . ?
C17 C18 C19 123.5(2) . . ?
N27 C16 C15 115.9(2) . . ?
N27 C16 H16 106.5 . . ?
N27 C16 C17 110.7(2) . . ?
C15 C16 H16 106.5 . . ?
C17 C16 C15 110.0(2) . . ?
C17 C16 H16 106.5 . . ?
O3 C25 N28 121.5(2) . . ?
O3 C25 C26 122.1(2) . . ?
N28 C25 C26 116.4(2) . . ?
C20 C19 C18 121.3(2) . . ?
C24 C19 C18 120.2(3) . . ?
C24 C19 C20 118.4(3) . . ?
N27 C7 C8 108.0(2) . . ?
N27 C7 C6 109.6(2) . . ?
N27 C7 C14 107.6(2) . . ?
C8 C7 C6 110.1(2) . . ?
C14 C7 C8 113.5(2) . . ?
C14 C7 C6 107.9(2) . . ?
C13 C8 C7 123.2(2) . . ?
C13 C8 C9 118.4(2) . . ?
C9 C8 C7 118.4(2) . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.3(2) . . ?
C1 C6 C7 121.7(2) . . ?
C1 C6 C5 118.0(3) . . ?
C18 C17 C16 124.1(2) . . ?
C18 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
O1 C14 C7 113.0(2) . . ?
O1 C14 H14A 109.0 . . ?
O1 C14 H14B 109.0 . . ?
C7 C14 H14A 109.0 . . ?
C7 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C8 C13 H13 119.6 . . ?
C8 C13 C12 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C19 C24 H24 119.6 . . ?
C19 C24 C23 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.7(4) . . ?
C22 C23 H23 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C15 1.214(3) . ?
O3 C25 1.233(3) . ?
O1 C15 1.328(4) . ?
O1 C14 1.444(4) . ?
N27 C16 1.464(3) . ?
N27 C7 1.477(3) . ?
N27 H27 0.89(3) . ?
N28 H28 0.8800 . ?
N28 C18 1.428(3) . ?
N28 C25 1.340(3) . ?
C15 C16 1.519(4) . ?
C18 C19 1.491(4) . ?
C18 C17 1.319(4) . ?
C16 H16 1.0000 . ?
C16 C17 1.502(3) . ?
C25 C26 1.502(4) . ?
C19 C20 1.388(4) . ?
C19 C24 1.372(4) . ?
C7 C8 1.534(3) . ?
C7 C6 1.537(4) . ?
C7 C14 1.528(4) . ?
C8 C13 1.376(4) . ?
C8 C9 1.400(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C5 C4 1.391(4) . ?
C6 C1 1.383(4) . ?
C17 H17 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.385(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.395(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(5) . ?
C3 C2 1.360(5) . ?
C4 H4 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.385(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.398(4) . ?
C2 H2 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(6) . ?
C24 H24 0.9500 . ?
C24 C23 1.400(5) . ?
C11 H11 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.376(6) . ?
C23 H23 0.9500 . ?
