#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:19:09 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/09/7240919.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_7240919
loop_
_publ_author_name
'Zhao, Kai'
'Zhang, Xiao-Chen'
'Tao, Ji-Yu'
'Wu, Xian-Dan'
'Wu, Jia-Xu'
'Li, Wei-Ming'
'Zhu, Tong-Hao'
'Loh, Teck-Peng'
_publ_section_title
;
 Regio- and stereoselective C(sp2)--H acylation of enamides with aldehydes
 via transition-metal-free photoredox catalysis
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              5497
_journal_page_last               5503
_journal_paper_doi               10.1039/D0GC01947J
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C22 H25 N O2'
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.007(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9186(12)
_cell_length_b                   11.6675(10)
_cell_length_c                   13.3986(12)
_cell_measurement_reflns_used    8692
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      54.849
_cell_measurement_theta_min      4.561
_cell_volume                     1909.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      185.32
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.029
_diffrn_reflns_theta_min         4.560
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.7200
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1630 before and 0.1199 after correction. The Ratio of minimum to maximum transmission is 0.7564. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1453P)²+0.3254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2161
_refine_ls_wR_factor_ref         0.2502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2530
_reflns_number_total             3621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc01947j2.cif
_cod_data_source_block           200525sf_0m
_cod_depositor_comments
;Adding full bibliography for 7240916--7240920.cif.

 Adding full bibliography for 7240916--7240920.cif.
;
_cod_database_code               7240919
_shelx_shelxl_version_number     2016/6
_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   0.982
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.39480(14) 0.60607(16) 0.43313(16) 0.0734(6) Uani 1 1 d . . . . .
O2 O 0.51177(15) 0.75054(17) 0.69895(15) 0.0800(6) Uani 1 1 d . . . . .
N1 N 0.33615(14) 0.74882(16) 0.59237(14) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.25205(17) 0.77770(19) 0.49491(17) 0.0501(6) Uani 1 1 d . . . . .
C2 C 0.23219(18) 0.7096(2) 0.41158(17) 0.0540(6) Uani 1 1 d . . . . .
H2 H 0.172170 0.729321 0.351048 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2951(2) 0.6051(2) 0.40409(17) 0.0545(6) Uani 1 1 d . . . . .
C4 C 0.23274(19) 0.49887(19) 0.35942(17) 0.0544(6) Uani 1 1 d . . . . .
C5 C 0.2902(2) 0.3975(2) 0.3629(2) 0.0662(7) Uani 1 1 d . . . . .
H5 H 0.367815 0.397437 0.391652 0.079 Uiso 1 1 calc R . . . .
C6 C 0.2356(3) 0.2971(2) 0.3250(2) 0.0757(8) Uani 1 1 d . . . . .
H6 H 0.275906 0.228315 0.328129 0.091 Uiso 1 1 calc R . . . .
C7 C 0.1237(3) 0.2956(3) 0.2826(2) 0.0817(9) Uani 1 1 d . . . . .
H7 H 0.086412 0.225967 0.256744 0.098 Uiso 1 1 calc R . . . .
C8 C 0.0653(3) 0.3959(3) 0.2778(2) 0.0830(9) Uani 1 1 d . . . . .
H8 H -0.012182 0.395426 0.247729 0.100 Uiso 1 1 calc R . . . .
C9 C 0.1192(2) 0.4968(2) 0.3165(2) 0.0687(7) Uani 1 1 d . . . . .
H9 H 0.078485 0.565193 0.313740 0.082 Uiso 1 1 calc R . . . .
C10 C 0.1810(2) 0.8836(2) 0.4953(2) 0.0628(7) Uani 1 1 d . . . . .
C11 C 0.2322(3) 0.9606(3) 0.5910(2) 0.0889(10) Uani 1 1 d . . . . .
H11A H 0.241212 0.917076 0.655817 0.133 Uiso 1 1 calc GR . . . .
H11B H 0.184426 1.026584 0.588059 0.133 Uiso 1 1 calc GR . . . .
H11C H 0.303904 0.987414 0.590367 0.133 Uiso 1 1 calc GR . . . .
C12 C 0.1666(3) 0.9539(3) 0.3956(2) 0.0908(10) Uani 1 1 d . . . . .
H12A H 0.238461 0.978834 0.393876 0.136 Uiso 1 1 calc GR . . . .
H12B H 0.121225 1.021248 0.395532 0.136 Uiso 1 1 calc GR . . . .
H12C H 0.130887 0.906851 0.333261 0.136 Uiso 1 1 calc GR . . . .
C13 C 0.0676(2) 0.8432(3) 0.4930(4) 0.1005(12) Uani 1 1 d . . . . .
H13A H 0.038132 0.789357 0.434427 0.151 Uiso 1 1 calc GR . . . .
H13B H 0.018591 0.909310 0.483406 0.151 Uiso 1 1 calc GR . . . .
H13C H 0.073490 0.804884 0.559741 0.151 Uiso 1 1 calc GR . . . .
C14 C 0.44291(19) 0.7782(2) 0.61505(19) 0.0593(6) Uani 1 1 d . . . . .
C15 C 0.4745(2) 0.8472(3) 0.5355(2) 0.0780(8) Uani 1 1 d . . . . .
H15A H 0.515369 0.915175 0.569634 0.117 Uiso 1 1 calc GR . . . .
H15B H 0.408419 0.870930 0.478813 0.117 Uiso 1 1 calc GR . . . .
H15C H 0.520521 0.800557 0.505814 0.117 Uiso 1 1 calc GR . . . .
C16 C 0.3015(2) 0.6847(2) 0.67094(19) 0.0632(7) Uani 1 1 d . . . . .
H16A H 0.234938 0.721150 0.677694 0.076 Uiso 1 1 calc R . . . .
H16B H 0.359848 0.690358 0.740340 0.076 Uiso 1 1 calc R . . . .
C17 C 0.2780(2) 0.5603(2) 0.64406(17) 0.0580(6) Uani 1 1 d . . . . .
C18 C 0.3609(2) 0.4843(3) 0.6494(2) 0.0740(8) Uani 1 1 d . . . . .
H18 H 0.434555 0.510335 0.669538 0.089 Uiso 1 1 calc R . . . .
C19 C 0.3373(4) 0.3710(3) 0.6257(3) 0.0954(10) Uani 1 1 d . . . . .
H19 H 0.394807 0.318900 0.628719 0.114 Uiso 1 1 calc R . . . .
C20 C 0.2312(4) 0.3319(3) 0.5975(3) 0.1039(13) Uani 1 1 d . . . . .
H20 H 0.215390 0.253006 0.582258 0.125 Uiso 1 1 calc R . . . .
C21 C 0.1485(3) 0.4079(3) 0.5916(3) 0.0998(12) Uani 1 1 d . . . . .
H21 H 0.074813 0.382163 0.571354 0.120 Uiso 1 1 calc R . . . .
C22 C 0.1725(2) 0.5207(3) 0.6149(2) 0.0778(8) Uani 1 1 d . . . . .
H22 H 0.114732 0.572830 0.610753 0.093 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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C1 N1 C16 116.83(18) . . ?
C14 N1 C1 123.8(2) . . ?
C14 N1 C16 119.40(19) . . ?
N1 C1 C10 117.33(19) . . ?
C2 C1 N1 120.3(2) . . ?
C2 C1 C10 122.1(2) . . ?
C1 C2 H2 117.0 . . ?
C1 C2 C3 126.0(2) . . ?
C3 C2 H2 117.0 . . ?
O1 C3 C2 121.1(2) . . ?
O1 C3 C4 120.8(2) . . ?
C2 C3 C4 118.2(2) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C9 118.6(2) . . ?
C9 C4 C3 122.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C1 112.2(2) . . ?
C11 C10 C13 110.4(3) . . ?
C12 C10 C1 109.3(2) . . ?
C12 C10 C11 108.3(2) . . ?
C12 C10 C13 107.8(3) . . ?
C13 C10 C1 108.7(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N1 121.3(2) . . ?
O2 C14 C15 120.6(2) . . ?
N1 C14 C15 118.1(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
N1 C16 C17 113.82(19) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C17 C16 121.1(2) . . ?
C22 C17 C16 120.0(3) . . ?
C22 C17 C18 118.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
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
O1 C3 1.218(3) . ?
O2 C14 1.228(3) . ?
N1 C1 1.440(3) . ?
N1 C14 1.356(3) . ?
N1 C16 1.474(3) . ?
C1 C2 1.326(3) . ?
C1 C10 1.540(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.486(3) . ?
C3 C4 1.494(3) . ?
C4 C5 1.389(3) . ?
C4 C9 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.528(4) . ?
C10 C12 1.527(4) . ?
C10 C13 1.529(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.495(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.503(4) . ?
C17 C18 1.375(4) . ?
C17 C22 1.370(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.371(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(5) . ?
C22 H22 0.9500 . ?
