#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:55:36 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245190.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_7245190
loop_
_publ_author_name
'Qu, Zhonghua'
'Tian, Tong'
'Tan, Yongbo'
'Ji, Xiaochen'
'Deng, Guo-Jun'
'Huang, Huawen'
_publ_section_title
;
 Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl
 acrylamides through consecutive photoinduced electron transfer
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7403
_journal_page_last               7409
_journal_paper_doi               10.1039/D2GC01966C
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                94.614(8)
_cell_angle_beta                 101.272(8)
_cell_angle_gamma                99.213(7)
_cell_formula_units_Z            2
_cell_length_a                   7.8246(6)
_cell_length_b                   9.2051(7)
_cell_length_c                   10.7849(12)
_cell_measurement_reflns_used    2599
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      29.0250
_cell_measurement_theta_min      2.6780
_cell_volume                     746.96(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  59.00   1.00    1.20    --  -11.43  57.00  30.00   99
  2  ω    -79.00  11.00   1.00    1.20    --  -11.43 -57.00-120.00   90
  3  ω    -15.00  77.00   1.00    1.20    --   12.05  77.00 150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0109620000
_diffrn_orient_matrix_UB_12      -0.0252344000
_diffrn_orient_matrix_UB_13      -0.0613617000
_diffrn_orient_matrix_UB_21      0.0706826000
_diffrn_orient_matrix_UB_22      -0.0342571000
_diffrn_orient_matrix_UB_23      0.0281516000
_diffrn_orient_matrix_UB_31      -0.0609367000
_diffrn_orient_matrix_UB_32      -0.0660735000
_diffrn_orient_matrix_UB_33      -0.0004289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.938
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0469
_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)+(0.0633P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2228
_reflns_number_total             2633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc01966c2.cif
_cod_data_source_block           3064
_cod_depositor_comments
'Adding full bibliography for 7245189--7245190.cif.'
_cod_database_code               7245190
_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   0.990
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.391
_oxdiff_exptl_absorpt_empirical_full_min 0.642
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.64645(15) 0.11554(13) 0.43413(11) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.39681(14) 0.19836(13) 0.60842(10) 0.0306(3) Uani 1 1 d . . . . .
H2 H 0.375799 0.108902 0.586094 0.046 Uiso 1 1 calc R U . . .
N1 N 0.71910(16) 0.36628(15) 0.49065(12) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.81995(19) 0.46311(17) 0.59580(14) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.8620(2) 0.61573(19) 0.60885(17) 0.0346(4) Uani 1 1 d . . . . .
H2A H 0.820538 0.669690 0.543642 0.041 Uiso 1 1 calc R U . . .
C3 C 0.9685(2) 0.6856(2) 0.72316(18) 0.0420(5) Uani 1 1 d . . . . .
H3 H 1.000763 0.788226 0.734093 0.050 Uiso 1 1 calc R U . . .
C4 C 1.0275(2) 0.6061(2) 0.82080(17) 0.0433(5) Uani 1 1 d . . . . .
H4 H 1.097865 0.655468 0.896786 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9822(2) 0.45224(19) 0.80621(16) 0.0349(4) Uani 1 1 d . . . . .
H5 H 1.021467 0.398555 0.872205 0.042 Uiso 1 1 calc R U . . .
C6 C 0.87897(18) 0.38063(17) 0.69341(14) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.80765(19) 0.21834(16) 0.65048(14) 0.0239(4) Uani 1 1 d . . . . .
C8 C 0.67620(19) 0.15316(17) 0.73069(14) 0.0248(4) Uani 1 1 d . . . . .
H8A H 0.634059 0.049142 0.699845 0.030 Uiso 1 1 calc R U . . .
H8B H 0.739846 0.158964 0.818181 0.030 Uiso 1 1 calc R U . . .
C9 C 0.51637(19) 0.22874(17) 0.72899(13) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.561166 0.335725 0.742167 0.029 Uiso 1 1 calc R U . . .
C10 C 0.42404(18) 0.19269(17) 0.83694(14) 0.0245(4) Uani 1 1 d . . . . .
C11 C 0.4090(2) 0.3047(2) 0.92419(17) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.456766 0.402052 0.916819 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3236(3) 0.2750(2) 1.02314(18) 0.0465(5) Uani 1 1 d . . . . .
H12 H 0.314974 0.351993 1.081686 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2517(2) 0.1316(2) 1.03432(16) 0.0392(5) Uani 1 1 d . . . . .
H13 H 0.194125 0.111046 1.100290 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2655(2) 0.0193(2) 0.94796(15) 0.0345(4) Uani 1 1 d . . . . .
H14 H 0.216493 -0.077737 0.955360 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3513(2) 0.04827(18) 0.84971(14) 0.0296(4) Uani 1 1 d . . . . .
H15 H 0.360380 -0.029293 0.791933 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9521(2) 0.1242(2) 0.65353(17) 0.0365(4) Uani 1 1 d . . . . .
H16A H 0.900187 0.025812 0.613720 0.055 Uiso 1 1 calc R U . . .
H16B H 1.008766 0.120112 0.740254 0.055 Uiso 1 1 calc R U . . .
H16C H 1.038234 0.167622 0.608553 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6363(2) 0.4129(2) 0.37198(16) 0.0409(5) Uani 1 1 d . . . . .
H17A H 0.555560 0.476922 0.388081 0.061 Uiso 1 1 calc R U . . .
H17B H 0.572639 0.327505 0.314922 0.061 Uiso 1 1 calc R U . . .
H17C H 0.725635 0.465221 0.334243 0.061 Uiso 1 1 calc R U . . .
C18 C 0.71302(19) 0.22202(18) 0.51290(14) 0.0260(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C1 N1 C17 124.46(14) . . ?
C18 N1 C1 111.39(12) . . ?
C18 N1 C17 124.13(15) . . ?
C2 C1 N1 128.87(14) . . ?
C2 C1 C6 122.02(16) . . ?
C6 C1 N1 109.11(13) . . ?
C1 C2 H2A 121.3 . . ?
C1 C2 C3 117.36(15) . . ?
C3 C2 H2A 121.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.46(16) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.30(17) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.29(16) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 109.01(13) . . ?
C5 C6 C1 119.57(15) . . ?
C5 C6 C7 131.41(14) . . ?
C6 C7 C8 111.39(12) . . ?
C6 C7 C16 113.48(12) . . ?
C6 C7 C18 101.74(12) . . ?
C16 C7 C8 109.02(12) . . ?
C16 C7 C18 109.90(13) . . ?
C18 C7 C8 111.16(12) . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.23(11) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
O2 C9 C8 111.61(12) . . ?
O2 C9 H9 106.8 . . ?
O2 C9 C10 111.93(11) . . ?
C8 C9 H9 106.8 . . ?
C10 C9 C8 112.43(11) . . ?
C10 C9 H9 106.8 . . ?
C11 C10 C9 119.92(14) . . ?
C11 C10 C15 118.42(13) . . ?
C15 C10 C9 121.66(14) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.12(16) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.80(17) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.62(15) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.77(15) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.26(16) . . ?
C14 C15 H15 119.9 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 N1 124.86(14) . . ?
O1 C18 C7 126.62(14) . . ?
N1 C18 C7 108.49(13) . . ?
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 C18 1.2180(19) . ?
O2 H2 0.8200 . ?
O2 C9 1.4235(18) . ?
N1 C1 1.402(2) . ?
N1 C17 1.448(2) . ?
N1 C18 1.363(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.396(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(2) . ?
C6 C7 1.509(2) . ?
C7 C8 1.5492(18) . ?
C7 C16 1.527(2) . ?
C7 C18 1.529(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.5171(19) . ?
C10 C11 1.374(2) . ?
C10 C15 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -113.09(16) . . . . ?
O2 C9 C10 C15 66.09(18) . . . . ?
N1 C1 C2 C3 -178.53(14) . . . . ?
N1 C1 C6 C5 179.47(13) . . . . ?
N1 C1 C6 C7 -1.61(16) . . . . ?
C1 N1 C18 O1 -173.89(13) . . . . ?
C1 N1 C18 C7 4.50(16) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C6 C7 C8 -114.54(13) . . . . ?
C1 C6 C7 C16 121.97(14) . . . . ?
C1 C6 C7 C18 3.97(14) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C6 C7 178.84(13) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 -179.19(15) . . . . ?
C5 C6 C7 C8 64.2(2) . . . . ?
C5 C6 C7 C16 -59.3(2) . . . . ?
C5 C6 C7 C18 -177.29(15) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C7 C8 C9 58.25(17) . . . . ?
C6 C7 C18 O1 173.29(14) . . . . ?
C6 C7 C18 N1 -5.07(15) . . . . ?
C7 C8 C9 O2 70.35(16) . . . . ?
C7 C8 C9 C10 -162.91(13) . . . . ?
C8 C7 C18 O1 -68.03(19) . . . . ?
C8 C7 C18 N1 113.62(13) . . . . ?
C8 C9 C10 C11 120.35(16) . . . . ?
C8 C9 C10 C15 -60.47(18) . . . . ?
C9 C10 C11 C12 179.34(16) . . . . ?
C9 C10 C15 C14 -178.94(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C16 C7 C8 C9 -175.76(13) . . . . ?
C16 C7 C18 O1 52.75(19) . . . . ?
C16 C7 C18 N1 -125.60(13) . . . . ?
C17 N1 C1 C2 -0.6(2) . . . . ?
C17 N1 C1 C6 179.89(14) . . . . ?
C17 N1 C18 O1 4.4(2) . . . . ?
C17 N1 C18 C7 -177.26(13) . . . . ?
C18 N1 C1 C2 177.64(14) . . . . ?
C18 N1 C1 C6 -1.87(17) . . . . ?
C18 C7 C8 C9 -54.45(18) . . . . ?
