#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:14:55 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135386.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_4135386
loop_
_publ_author_name
'Luan, Zi-Hong'
'Qu, Jian-Ping'
'Kang, Yan-Biao'
_publ_section_title
;
 Discovery of Oxygen α-Nucleophilic Addition to α,β-Unsaturated Amides
 Catalyzed by Redox-Neutral Organic Photoreductant.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20942
_journal_page_last               20947
_journal_paper_doi               10.1021/jacs.0c10707
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-25
_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                   8.70779(14)
_cell_length_b                   9.8648(2)
_cell_length_c                   18.3289(3)
_cell_measurement_reflns_used    3069
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.8340
_cell_measurement_theta_min      5.0190
_cell_volume                     1574.46(5)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4204
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.952
_diffrn_reflns_theta_min         4.825
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_coef       0.0073(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0550P)²+0.0985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_full    0.730
_reflns_Friedel_fraction_max     0.687
_reflns_number_gt                2578
_reflns_number_total             2681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c10707_si_004.cif
_cod_data_source_block           lzh-ome
_cod_depositor_comments
'Adding full bibliography for 4135385--4135388.cif.'
_cod_original_cell_volume        1574.47(5)
_cod_database_code               4135386
_shelxl_version_number           2013-4
_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   0.889
_shelx_estimated_absorpt_t_min   0.867
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C11(H11), C10(H10), C13(H13), C4(H4), C5(H5), C1(H1A),
 C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
N1 N 0.84597(17) 0.49677(15) 0.08080(8) 0.0401(3) Uani 1 1 d . . . . .
H1 H 0.7941 0.4818 0.0417 0.048 Uiso 1 1 calc R . . . .
O3 O 1.18457(19) 0.97566(15) 0.07027(8) 0.0594(4) Uani 1 1 d . . . . .
O2 O 0.70792(16) 0.28358(15) 0.03951(7) 0.0512(4) Uani 1 1 d . . . . .
C12 C 1.1034(2) 0.85738(19) 0.07789(10) 0.0446(4) Uani 1 1 d . . . . .
C9 C 0.93471(18) 0.61707(18) 0.08219(9) 0.0375(4) Uani 1 1 d . . . . .
C14 C 0.9752(3) 0.6755(2) 0.01618(10) 0.0501(5) Uani 1 1 d . . . . .
H14 H 0.9460 0.6339 -0.0272 0.060 Uiso 1 1 calc R . . . .
C11 C 1.0654(2) 0.7992(2) 0.14377(10) 0.0486(5) Uani 1 1 d . . . . .
H11 H 1.0970 0.8398 0.1870 0.058 Uiso 1 1 calc R . . . .
O1 O 0.8980(2) 0.4124(2) 0.19269(8) 0.0775(6) Uani 1 1 d . . . . .
C10 C 0.9802(2) 0.6802(2) 0.14593(10) 0.0469(4) Uani 1 1 d . . . . .
H10 H 0.9535 0.6427 0.1907 0.056 Uiso 1 1 calc R . . . .
C7 C 0.7290(2) 0.2817(2) 0.11681(11) 0.0458(4) Uani 1 1 d . . . . .
C13 C 1.0582(3) 0.7944(2) 0.01394(11) 0.0561(6) Uani 1 1 d . . . . .
H13 H 1.0840 0.8325 -0.0308 0.067 Uiso 1 1 calc R . . . .
C8 C 0.8341(2) 0.4038(2) 0.13387(10) 0.0451(4) Uani 1 1 d . . . . .
C15 C 1.2414(3) 1.0385(3) 0.13429(13) 0.0636(6) Uani 1 1 d . . . . .
H15A H 1.1572 1.0617 0.1657 0.095 Uiso 1 1 calc GR . . . .
H15B H 1.2967 1.1192 0.1213 0.095 Uiso 1 1 calc GR . . . .
H15C H 1.3090 0.9771 0.1593 0.095 Uiso 1 1 calc GR . . . .
C6 C 0.5775(2) 0.3083(2) 0.15638(12) 0.0508(5) Uani 1 1 d . . . . .
C4 C 0.3342(3) 0.4249(3) 0.1616(2) 0.0879(10) Uani 1 1 d . . . . .
H4 H 0.2640 0.4845 0.1407 0.105 Uiso 1 1 calc R . . . .
C17 C 0.6158(3) 0.1789(3) 0.00936(14) 0.0724(7) Uani 1 1 d . . . . .
H17A H 0.5187 0.1763 0.0341 0.109 Uiso 1 1 calc GR . . . .
H17B H 0.6671 0.0934 0.0151 0.109 Uiso 1 1 calc GR . . . .
H17C H 0.5994 0.1963 -0.0416 0.109 Uiso 1 1 calc GR . . . .
C16 C 0.8097(3) 0.1521(3) 0.14062(16) 0.0700(7) Uani 1 1 d . . . . .
H16A H 0.8956 0.1351 0.1091 0.105 Uiso 1 1 calc GR . . . .
H16B H 0.7391 0.0775 0.1379 0.105 Uiso 1 1 calc GR . . . .
H16C H 0.8452 0.1619 0.1899 0.105 Uiso 1 1 calc GR . . . .
C5 C 0.4715(3) 0.3959(3) 0.12586(16) 0.0664(6) Uani 1 1 d . . . . .
H5 H 0.4922 0.4359 0.0810 0.080 Uiso 1 1 calc R . . . .
C1 C 0.5430(3) 0.2501(3) 0.22296(14) 0.0731(7) Uani 1 1 d . . . . .
H1A H 0.6121 0.1904 0.2445 0.088 Uiso 1 1 calc R . . . .
C3 C 0.3027(4) 0.3655(4) 0.2273(2) 0.0986(12) Uani 1 1 d . . . . .
H3 H 0.2105 0.3838 0.2510 0.118 Uiso 1 1 calc R . . . .
C2 C 0.4055(4) 0.2803(4) 0.25787(18) 0.0989(12) Uani 1 1 d . . . . .
H2 H 0.3841 0.2412 0.3029 0.119 Uiso 1 1 calc R . . . .
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
C8 N1 C9 127.03(15) . . ?
C12 O3 C15 117.90(16) . . ?
C17 O2 C7 116.71(17) . . ?
O3 C12 C11 124.59(17) . . ?
O3 C12 C13 116.25(17) . . ?
C11 C12 C13 119.16(16) . . ?
C14 C9 N1 118.15(15) . . ?
C10 C9 N1 123.31(15) . . ?
C10 C9 C14 118.53(16) . . ?
C13 C14 C9 120.90(17) . . ?
C12 C11 C10 120.35(17) . . ?
C9 C10 C11 120.65(16) . . ?
O2 C7 C8 105.49(14) . . ?
O2 C7 C6 110.92(16) . . ?
O2 C7 C16 110.74(19) . . ?
C6 C7 C8 106.36(16) . . ?
C16 C7 C8 108.89(17) . . ?
C16 C7 C6 113.97(18) . . ?
C14 C13 C12 120.40(17) . . ?
N1 C8 C7 115.61(15) . . ?
O1 C8 N1 124.03(18) . . ?
O1 C8 C7 120.35(17) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 122.4(2) . . ?
C1 C6 C5 118.2(2) . . ?
C3 C4 C5 119.9(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C1 C2 120.3(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C2 C1 121.0(3) . . ?
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
N1 C9 1.416(2) . ?
N1 C8 1.341(2) . ?
O3 C12 1.371(2) . ?
O3 C15 1.416(3) . ?
O2 C7 1.429(2) . ?
O2 C17 1.419(3) . ?
C12 C11 1.377(3) . ?
C12 C13 1.384(3) . ?
C9 C14 1.386(2) . ?
C9 C10 1.382(2) . ?
C14 C13 1.378(3) . ?
C11 C10 1.389(3) . ?
O1 C8 1.216(2) . ?
C7 C8 1.544(3) . ?
C7 C6 1.529(3) . ?
C7 C16 1.523(3) . ?
C6 C5 1.382(3) . ?
C6 C1 1.382(3) . ?
C4 C5 1.393(4) . ?
C4 C3 1.368(5) . ?
C1 C2 1.389(4) . ?
C3 C2 1.350(6) . ?
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
_geom_hbond_site_symmetry_A
N1 H1 O3 0.86 2.30 3.117(2) 158.3 3_465
N1 H1 O2 0.86 2.09 2.538(2) 111.4 .
