#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:20:05 +0300 (Fri, 05 May 2023) $
#$Revision: 283463 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159249.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_7159249
loop_
_publ_author_name
'Zhang, Zhang'
'Wang, Ying-Chun'
'Tang, Hai-Tao'
'Pan, Ying-Ming'
'Meng, Xiu-Jin'
_publ_section_title
;
 Electrocatalytic ring-opening dihydroalkoxylation of N-aryl
 maleimides with alcohols under metal- and oxidant-free conditions.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3177
_journal_page_last               3182
_journal_paper_doi               10.1039/d3ob00178d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C18 H19 N O4'
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2d6dvw
_audit_creation_date             2022-08-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-02 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.192(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.340(4)
_cell_length_b                   5.3646(6)
_cell_length_c                   10.6018(13)
_cell_measurement_reflns_used    835
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      70.4320
_cell_measurement_theta_min      3.2380
_cell_volume                     1550.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00 124.00   0.50    0.50    --   41.80   0.00 120.00  252
  2  ω    -15.00  60.00   0.50    0.50    --   41.80 -57.00  90.00  150
  3  ω     84.00 110.00   0.50    0.50    --   41.80  77.00 120.00   52
  4  ω     38.00 134.00   0.50    1.00    --  102.30 -50.00-150.00  192
  5  ω     56.00 172.00   0.50    1.00    --  102.30  38.00   0.00  232
  6  ω     25.00  74.00   0.50    1.00    --  102.30 -64.00-150.00   98
  7  ω     66.00  92.00   0.50    1.00    --  102.30 -77.00 -60.00   52
  8  ω     14.00  40.00   0.50    1.00    --  102.30 -77.00  60.00   52
  9  ω     47.00 142.00   0.50    1.00    --  102.30 -77.00  60.00  190
 10  ω     83.00 121.00   0.50    1.00    --  102.30 -64.00-150.00   76
 11  ω     90.00 136.00   0.50    1.00    --  102.30  82.00 -30.00   92
 12  ω     14.00 126.00   0.50    1.00    --  102.30 -64.00  60.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0516080000
_diffrn_orient_matrix_UB_12      -0.0200079000
_diffrn_orient_matrix_UB_13      0.0679970000
_diffrn_orient_matrix_UB_21      -0.0223293000
_diffrn_orient_matrix_UB_22      -0.1091335000
_diffrn_orient_matrix_UB_23      0.1173032000
_diffrn_orient_matrix_UB_31      0.0053641000
_diffrn_orient_matrix_UB_32      -0.2647989000
_diffrn_orient_matrix_UB_33      -0.0534681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5702
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.242
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.1125
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2955
_refine_ls_wR_factor_ref         0.3212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2729
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00178d2.cif
_cod_data_source_block           b-0817
_cod_depositor_comments          'Adding full bibliography for 7159249.cif.'
_cod_database_code               7159249
_shelx_shelxl_version_number     2017/1
_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.
;
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11),
 C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 2.061
_oxdiff_exptl_absorpt_empirical_full_min 0.488
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.70777(10) 0.0800(5) 0.5707(3) 0.0306(8) Uani 1 1 d . . . . .
O2 O 0.64098(10) 0.6083(5) 0.4410(3) 0.0267(7) Uani 1 1 d . . . . .
O3 O 0.56655(10) 0.2337(5) 0.2997(3) 0.0254(7) Uani 1 1 d . . . . .
O4 O 0.52107(9) 0.2484(4) 0.4665(3) 0.0207(7) Uani 1 1 d . . . . .
N1 N 0.71963(12) 0.4959(6) 0.5971(3) 0.0262(8) Uani 1 1 d . . . . .
H1 H 0.709081 0.639499 0.571306 0.031 Uiso 1 1 calc R U . . .
C1 C 0.9171(2) 0.6891(12) 0.9744(5) 0.0603(18) Uani 1 1 d . . . . .
H1A H 0.915444 0.809632 0.911207 0.072 Uiso 1 1 calc R U . . .
C2 C 0.9549(3) 0.6956(13) 1.0672(6) 0.074(2) Uani 1 1 d . . . . .
H2 H 0.978341 0.821107 1.065662 0.088 Uiso 1 1 calc R U . . .
C3 C 0.95891(16) 0.5205(8) 1.1624(4) 0.0340(11) Uani 1 1 d . . . . .
H3 H 0.984805 0.525142 1.224299 0.041 Uiso 1 1 calc R U . . .
C4 C 0.92385(18) 0.3402(10) 1.1632(6) 0.0483(14) Uani 1 1 d . . . . .
H4 H 0.925576 0.220653 1.226884 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8858(2) 0.3333(11) 1.0702(6) 0.0569(17) Uani 1 1 d . . . . .
H5 H 0.862305 0.208151 1.072638 0.068 Uiso 1 1 calc R U . . .
C6 C 0.88142(14) 0.5069(7) 0.9734(4) 0.0263(9) Uani 1 1 d . . . . .
C7 C 0.84031(14) 0.5017(7) 0.8740(4) 0.0241(9) Uani 1 1 d . . . . .
C8 C 0.8336(2) 0.6849(10) 0.7819(6) 0.0538(17) Uani 1 1 d . . . . .
H8 H 0.856162 0.814760 0.781458 0.065 Uiso 1 1 calc R U . . .
C9 C 0.79494(19) 0.6817(9) 0.6911(6) 0.0530(17) Uani 1 1 d . . . . .
H9 H 0.791689 0.808486 0.631289 0.064 Uiso 1 1 calc R U . . .
C10 C 0.76101(14) 0.4913(7) 0.6886(4) 0.0256(9) Uani 1 1 d . . . . .
C11 C 0.76669(19) 0.3035(11) 0.7789(5) 0.0445(13) Uani 1 1 d . . . . .
H11 H 0.744231 0.173272 0.778455 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8057(2) 0.3106(10) 0.8691(5) 0.0446(13) Uani 1 1 d . . . . .
H12 H 0.808949 0.183574 0.928837 0.054 Uiso 1 1 calc R U . . .
C13 C 0.69623(14) 0.2955(7) 0.5488(4) 0.0245(9) Uani 1 1 d . . . . .
C14 C 0.65087(14) 0.3522(7) 0.4572(4) 0.0244(9) Uani 1 1 d . . . . .
H14 H 0.656049 0.278993 0.374572 0.029 Uiso 1 1 calc R U . . .
C15 C 0.60666(14) 0.2293(7) 0.5090(4) 0.0212(9) Uani 1 1 d . . . . .
H15A H 0.614265 0.057109 0.530334 0.025 Uiso 1 1 calc R U . . .
H15B H 0.598499 0.314389 0.585375 0.025 Uiso 1 1 calc R U . . .
C16 C 0.56336(14) 0.2391(6) 0.4118(4) 0.0200(8) Uani 1 1 d . . . . .
C17 C 0.47697(14) 0.2478(7) 0.3820(4) 0.0238(9) Uani 1 1 d . . . . .
H17A H 0.477304 0.388955 0.326411 0.036 Uiso 1 1 calc R U . . .
H17B H 0.448750 0.257025 0.430642 0.036 Uiso 1 1 calc R U . . .
H17C H 0.475637 0.097175 0.333044 0.036 Uiso 1 1 calc R U . . .
C18 C 0.65776(18) 0.7103(8) 0.3270(4) 0.0320(10) Uani 1 1 d . . . . .
H18A H 0.648673 0.600934 0.257496 0.048 Uiso 1 1 calc R U . . .
H18B H 0.692795 0.727388 0.335762 0.048 Uiso 1 1 calc R U . . .
H18C H 0.643054 0.870843 0.311239 0.048 Uiso 1 1 calc R U . . .
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
C14 O2 C18 113.9(3) . . ?
C16 O4 C17 116.1(3) . . ?
C10 N1 H1 117.4 . . ?
C13 N1 H1 117.4 . . ?
C13 N1 C10 125.3(3) . . ?
C2 C1 H1A 119.4 . . ?
C2 C1 C6 121.2(5) . . ?
C6 C1 H1A 119.4 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(5) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(4) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.7(4) . . ?
C1 C6 C7 121.1(4) . . ?
C5 C6 C7 122.2(4) . . ?
C8 C7 C6 122.7(4) . . ?
C8 C7 C12 116.2(4) . . ?
C12 C7 C6 121.1(4) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.5(4) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 N1 119.8(4) . . ?
C9 C10 C11 118.8(4) . . ?
C11 C10 N1 121.4(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 118.9 . . ?
C11 C12 C7 122.3(4) . . ?
C11 C12 H12 118.9 . . ?
O1 C13 N1 125.6(4) . . ?
O1 C13 C14 119.4(3) . . ?
N1 C13 C14 115.0(3) . . ?
O2 C14 C13 113.9(3) . . ?
O2 C14 H14 108.7 . . ?
O2 C14 C15 108.5(3) . . ?
C13 C14 H14 108.7 . . ?
C15 C14 C13 108.2(3) . . ?
C15 C14 H14 108.7 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 110.1(3) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
O3 C16 O4 124.2(3) . . ?
O3 C16 C15 124.4(3) . . ?
O4 C16 C15 111.4(3) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C13 1.216(5) . ?
O2 C14 1.408(5) . ?
O2 C18 1.433(5) . ?
O3 C16 1.198(5) . ?
O4 C16 1.332(5) . ?
O4 C17 1.448(5) . ?
N1 H1 0.8600 . ?
N1 C10 1.436(5) . ?
N1 C13 1.334(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(8) . ?
C1 C6 1.380(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(7) . ?
C6 C7 1.484(6) . ?
C7 C8 1.388(6) . ?
C7 C12 1.394(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(6) . ?
C10 C11 1.391(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.548(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.514(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.513(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O1 C13 C14 O2 179.2(4) . . . . ?
O1 C13 C14 C15 58.5(5) . . . . ?
O2 C14 C15 C16 66.1(4) . . . . ?
N1 C10 C11 C12 -177.0(4) . . . . ?
N1 C13 C14 O2 -1.0(5) . . . . ?
N1 C13 C14 C15 -121.8(4) . . . . ?
C1 C2 C3 C4 -0.7(11) . . . . ?
C1 C6 C7 C8 -3.9(7) . . . . ?
C1 C6 C7 C12 176.7(5) . . . . ?
C2 C1 C6 C5 0.2(10) . . . . ?
C2 C1 C6 C7 179.4(6) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 C6 -0.1(10) . . . . ?
C4 C5 C6 C1 -0.2(9) . . . . ?
C4 C5 C6 C7 -179.4(5) . . . . ?
C5 C6 C7 C8 175.2(6) . . . . ?
C5 C6 C7 C12 -4.1(7) . . . . ?
C6 C1 C2 C3 0.3(12) . . . . ?
C6 C7 C8 C9 -178.8(5) . . . . ?
C6 C7 C12 C11 179.0(5) . . . . ?
C7 C8 C9 C10 -0.3(10) . . . . ?
C8 C7 C12 C11 -0.4(8) . . . . ?
C8 C9 C10 N1 177.2(5) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
C10 N1 C13 O1 -3.5(7) . . . . ?
C10 N1 C13 C14 176.7(3) . . . . ?
C10 C11 C12 C7 0.0(9) . . . . ?
C12 C7 C8 C9 0.6(9) . . . . ?
C13 N1 C10 C9 151.2(5) . . . . ?
C13 N1 C10 C11 -31.5(6) . . . . ?
C13 C14 C15 C16 -169.8(3) . . . . ?
C14 C15 C16 O3 31.5(5) . . . . ?
C14 C15 C16 O4 -150.0(3) . . . . ?
C17 O4 C16 O3 0.9(5) . . . . ?
C17 O4 C16 C15 -177.5(3) . . . . ?
C18 O2 C14 C13 100.2(4) . . . . ?
C18 O2 C14 C15 -139.2(3) . . . . ?
