Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and azides
Yang, Hongzhi; Zeng, Tianying; Xi, Shuang; Hu, Shengkun; Wu, Yunfei; Tang, Yefeng; Green Chemistry 22 (2020) 7023–7030; doi:10.1039/D0GC02347G

data_7241346
_publ_section_title
;
 Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and
 azides
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7023
_journal_page_last               7030
_journal_paper_doi               10.1039/D0GC02347G
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 N O2'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_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             2020-06-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-07-09 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.229(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1208(3)
_cell_length_b                   7.66440(10)
_cell_length_c                   15.2725(4)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      70.1420
_cell_measurement_theta_min      3.7750
_cell_volume                     1431.63(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -49.00  33.00   1.00    1.00    --  -40.81  38.00  30.00   82
  2  \w    -69.00  27.00   1.00    1.00    --  -40.81  77.00 120.00   96
  3  \w     73.00 158.00   1.00    1.00    --   98.72  30.00  60.00   85
  4  \w    101.00 164.00   1.00    1.00    --   98.72 125.00 -30.00   63
  5  \w    109.00 166.00   1.00    1.00    --   98.72  42.00  97.00   57
  6  \w     77.00 103.00   1.00    1.00    --   98.72  42.00  97.00   26
  7  \w     28.00 116.00   1.00    1.00    --   98.72 -45.00-120.00   88
  8  \w     18.00 107.00   1.00    1.00    --   98.72 -95.00 -90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289240000
_diffrn_orient_matrix_UB_12      -0.0987428000
_diffrn_orient_matrix_UB_13      0.0938129000
_diffrn_orient_matrix_UB_21      0.1151781000
_diffrn_orient_matrix_UB_22      -0.0375258000
_diffrn_orient_matrix_UB_23      -0.0004179000
_diffrn_orient_matrix_UB_31      0.0420263000
_diffrn_orient_matrix_UB_32      0.1709604000
_diffrn_orient_matrix_UB_33      0.0539391000
_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  0.0150
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5160
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.283
_diffrn_reflns_theta_min         3.818
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
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    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0376
_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/[\s^2^(Fo^2^)+(0.0450P)^2^+0.5289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             2665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc02347g2.cif
_cod_data_source_block           xs-3-87-2-2
_cod_depositor_comments
'Adding full bibliography for 7241345--7241346.cif.'
_cod_database_code               7241346
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONCl
_chemical_oxdiff_usercomment     'C H N O Fe Cl'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 Ternary CH refined with riding coordinates:
 C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E), C00G(H00G,H00H), C00H(H00I,H00J), C00J(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00F(H00F)
2.d Idealised Me refined as rotating group:
 C00C(H00A,H00B,H00C), C00I(H00K,H00L,H00M), C00K(H00P,H00Q,H00R)
;
_shelx_res_checksum              50067
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.838