#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:38:29 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570204.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_1570204
loop_
_publ_author_name
'Xiao, Yuanjiu'
'Xu, Tong-Tong'
'Zhou, Jin-Lan'
'Wu, Feng'
'Tang, Lei'
'Liu, Ruo-Yi'
'Wu, Wen-Biao'
'Feng, Jian-Jun'
_publ_section_title
;
 Photochemical α-selective radical ring-opening reactions of
 1,3-disubstituted acyl bicyclobutanes with alkyl halides: modular access
 to functionalized cyclobutenes.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13060
_journal_page_last               13066
_journal_paper_doi               10.1039/d3sc04457b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_systematic
methyl-1-(cyanomethyl)-3-phenylcyclobut-2-ene-1-carboxylate
_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             2023-07-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-08 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.998(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.84837(19)
_cell_length_b                   8.49086(12)
_cell_length_c                   14.3960(3)
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      71.5750
_cell_measurement_theta_min      4.3890
_cell_volume                     1229.50(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_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    -17.00  43.00   1.00    2.00    --   34.73 -57.00  90.00   60
  2  ω     31.00  73.00   1.00    2.00    --   34.73-125.00   0.00   42
  3  ω     36.00  85.00   1.00    8.00    --  105.25 -94.00 -30.00   49
  4  ω     88.00 174.00   1.00    8.00    --  105.25  45.00  90.00   86
  5  ω    116.00 162.00   1.00    8.00    --  105.25  77.00 120.00   46
  6  ω    107.00 140.00   1.00    8.00    --  105.25  96.00  19.00   33
  7  ω     83.00 111.00   1.00    8.00    --  105.25  77.00 120.00   28
  8  ω     44.00 102.00   1.00    2.00    --   34.73  77.00  60.00   58
  9  ω    106.00 161.00   1.00    8.00    --  105.25 111.00-180.00   55
 10  ω    -31.00  14.00   1.00    2.00    --   34.73 -77.00 -30.00   45
 11  ω     65.00  93.00   1.00    2.00    --   34.73  57.00 -90.00   28
 12  ω     20.00  56.00   1.00    2.00    --   34.73  57.00-150.00   36
 13  ω    -37.00  63.00   1.00    2.00    --   34.73 -19.00 150.00  100
 14  ω      3.00  73.00   1.00    2.00    --   34.73 -99.00  30.00   70
 15  ω     49.00  88.00   1.00    2.00    --   34.73-125.00-180.00   39
 16  ω     17.00  55.00   1.00    2.00    --   34.73 -99.00 -90.00   38
 17  ω     89.00 114.00   1.00    8.00    --  105.25 -45.00-120.00   25
 18  ω    113.00 152.00   1.00    8.00    --  105.25 111.00  30.00   39
 19  ω     45.00 127.00   1.00    8.00    --  105.25 -30.00  60.00   82
 20  ω     36.00 108.00   1.00    8.00    --  105.25-111.00-120.00   72
 21  ω     45.00  77.00   1.00    8.00    --  105.25 -45.00-120.00   32
 22  ω    112.00 138.00   1.00    8.00    --  105.25 111.00 -60.00   26
 23  ω     43.00 108.00   1.00    8.00    --  105.25 -94.00  30.00   65
 24  ω     76.00 121.00   1.00    8.00    --  105.25 -61.00   0.00   45
 25  ω     61.00 102.00   1.00    8.00    --  105.25 -94.00 120.00   41
 26  ω     47.00 108.00   1.00    8.00    --  105.25 -94.00 -90.00   61
 27  ω    100.00 143.00   1.00    8.00    --  105.25 111.00 150.00   43
 28  ω     44.00  70.00   1.00    8.00    --  105.25 -94.00-180.00   26
 29  ω     84.00 139.00   1.00    8.00    --  105.25  77.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1044367000
_diffrn_orient_matrix_UB_12      -0.0874469000
_diffrn_orient_matrix_UB_13      -0.0884212000
_diffrn_orient_matrix_UB_21      0.0291276000
_diffrn_orient_matrix_UB_22      -0.1531693000
_diffrn_orient_matrix_UB_23      0.0619404000
_diffrn_orient_matrix_UB_31      -0.1081371000
_diffrn_orient_matrix_UB_32      0.0431322000
_diffrn_orient_matrix_UB_33      0.0407444000
_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  0.0131
_diffrn_reflns_av_unetI/netI     0.0112
_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       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.403
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      3.501
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0481
_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)+(0.0796P)²+0.3909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04457b2.cif
_cod_data_source_block           exp_3129
_cod_depositor_comments          'Adding full bibliography for 1570204.cif.'
_cod_database_code               1570204
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C100 H100 N2 O2'
_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   0.936
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Restrained distances
 C7-C8
 2.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C10(H10)
3.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_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 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.530
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 0.21046(12) 0.40335(15) -0.00731(9) 0.0518(4) Uani 1 1 d . . . . .
N1 N 0.43062(19) 0.5124(2) 0.33448(13) 0.0688(5) Uani 1 1 d . . . . .
C1 C 0.5288(2) 0.8981(3) -0.16045(18) 0.0743(7) Uani 1 1 d . . . . .
H1 H 0.615015 0.888869 -0.158731 0.089 Uiso 1 1 calc R U . . .
O2 O 0.12838(15) 0.43314(17) 0.11260(11) 0.0630(4) Uani 1 1 d . . . . .
C2 C 0.4371(3) 0.9844(3) -0.23465(17) 0.0769(7) Uani 1 1 d . . . . .
H2 H 0.460565 1.032816 -0.283581 0.092 Uiso 1 1 calc R U . . .
C3 C 0.3106(3) 0.9991(3) -0.23649(18) 0.0762(7) Uani 1 1 d . . . . .
H3 H 0.248310 1.058123 -0.286733 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2745(2) 0.9268(2) -0.16407(15) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.188436 0.938231 -0.165644 0.070 Uiso 1 1 calc R U . . .
C5 C 0.36609(16) 0.83757(19) -0.08949(12) 0.0425(4) Uani 1 1 d . . . . .
C6 C 0.49423(19) 0.8244(3) -0.08800(15) 0.0571(5) Uani 1 1 d . . . . .
H6 H 0.557266 0.765718 -0.038018 0.068 Uiso 1 1 calc R U . . .
C7 C 0.32905(16) 0.75678(18) -0.01501(12) 0.0395(4) Uani 1 1 d D . . . .
C8 C 0.20469(17) 0.7566(2) 0.00294(12) 0.0438(4) Uani 1 1 d D . . . .
H8A H 0.129152 0.715550 -0.052555 0.053 Uiso 1 1 calc R U . . .
H8B H 0.183699 0.857184 0.025411 0.053 Uiso 1 1 calc R U . . .
C9 C 0.26825(15) 0.63587(19) 0.08891(11) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.39325(16) 0.6488(2) 0.06262(13) 0.0435(4) Uani 1 1 d . . . . .
H10 H 0.477396 0.603480 0.087860 0.052 Uiso 1 1 calc R U . . .
C11 C 0.28290(17) 0.6972(2) 0.19257(12) 0.0448(4) Uani 1 1 d . . . . .
H11A H 0.321963 0.801569 0.202065 0.054 Uiso 1 1 calc R U . . .
H11B H 0.195537 0.705821 0.195973 0.054 Uiso 1 1 calc R U . . .
C12 C 0.36576(18) 0.5943(2) 0.27299(13) 0.0468(4) Uani 1 1 d . . . . .
C13 C 0.19556(15) 0.48006(19) 0.06818(11) 0.0393(4) Uani 1 1 d . . . . .
C14 C 0.1339(2) 0.2602(2) -0.04028(16) 0.0617(5) Uani 1 1 d . . . . .
H14A H 0.155612 0.212366 -0.092653 0.093 Uiso 1 1 calc R U . . .
H14B H 0.040794 0.284814 -0.065091 0.093 Uiso 1 1 calc R U . . .
H14C H 0.154614 0.188464 0.015043 0.093 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
C13 O1 C14 116.71(14) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.74(17) . . ?
C4 C5 C7 120.99(16) . . ?
C6 C5 C7 120.26(16) . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C7 C8 131.22(15) . . ?
C10 C7 C5 134.54(15) . . ?
C10 C7 C8 94.22(13) . . ?
C7 C8 H8A 113.9 . . ?
C7 C8 H8B 113.9 . . ?
C7 C8 C9 88.74(12) . . ?
H8A C8 H8B 111.1 . . ?
C9 C8 H8A 113.9 . . ?
C9 C8 H8B 113.9 . . ?
C10 C9 C8 85.77(12) . . ?
C11 C9 C8 113.87(13) . . ?
C11 C9 C10 115.79(13) . . ?
C13 C9 C8 112.13(12) . . ?
C13 C9 C10 117.09(13) . . ?
C13 C9 C11 110.23(13) . . ?
C7 C10 C9 91.27(12) . . ?
C7 C10 H10 134.4 . . ?
C9 C10 H10 134.4 . . ?
C9 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C9 112.19(14) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N1 C12 C11 178.8(2) . . ?
O1 C13 C9 112.12(13) . . ?
O2 C13 O1 123.79(16) . . ?
O2 C13 C9 124.05(15) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 1.328(2) . ?
O1 C14 1.448(2) . ?
N1 C12 1.138(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(4) . ?
C1 C6 1.383(3) . ?
O2 C13 1.203(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 C6 1.387(2) . ?
C5 C7 1.451(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.466(2) . ?
C7 C10 1.411(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.555(2) . ?
C9 C10 1.542(2) . ?
C9 C11 1.531(2) . ?
C9 C13 1.512(2) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.460(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C7 -178.0(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C7 C8 -4.2(3) . . . . ?
C4 C5 C7 C10 173.29(19) . . . . ?
C5 C7 C8 C9 177.64(17) . . . . ?
C5 C7 C10 C9 -177.53(18) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C5 C7 C8 176.83(17) . . . . ?
C6 C5 C7 C10 -5.6(3) . . . . ?
C7 C5 C6 C1 178.35(19) . . . . ?
C7 C8 C9 C10 0.54(12) . . . . ?
C7 C8 C9 C11 116.93(14) . . . . ?
C7 C8 C9 C13 -117.04(13) . . . . ?
C8 C7 C10 C9 0.60(13) . . . . ?
C8 C9 C10 C7 -0.56(12) . . . . ?
C8 C9 C11 C12 -168.69(14) . . . . ?
C8 C9 C13 O1 68.38(17) . . . . ?
C8 C9 C13 O2 -109.32(19) . . . . ?
C10 C7 C8 C9 -0.59(13) . . . . ?
C10 C9 C11 C12 -71.54(19) . . . . ?
C10 C9 C13 O1 -28.44(19) . . . . ?
C10 C9 C13 O2 153.86(17) . . . . ?
C11 C9 C10 C7 -115.08(15) . . . . ?
C11 C9 C13 O1 -163.63(13) . . . . ?
C11 C9 C13 O2 18.7(2) . . . . ?
C13 C9 C10 C7 112.18(14) . . . . ?
C13 C9 C11 C12 64.29(18) . . . . ?
C14 O1 C13 O2 3.8(3) . . . . ?
C14 O1 C13 C9 -173.87(14) . . . . ?
