1,3-Dipolar [3 + 3] cycloaddition of α-halohydroxamate-based azaoxyallyl cations with hydrazonoyl chloride-derived nitrile imines
Zhao, Hong-Wu; Zhao, Yu-Di; Liu, Yue-Yang; Zhao, Li-Jiao; Song, Xiu-Qing; Chen, Xiao-Qin; Pang, Hai-Liang; Du, Juan; Feng, Ning-Ning; RSC Advances 7 (2017) 55106–; doi:10.1039/C7RA09766B

data_7229661
_publ_section_title
;
 1,3-Dipolar [3 + 3] cycloaddition of \a-halohydroxamate-based azaoxyallyl
 cations with hydrazonoyl chloride-derived nitrile imines
;
_journal_issue                   87
_journal_name_full               'RSC Advances'
_journal_page_first              55106
_journal_paper_doi               10.1039/C7RA09766B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C24 H22 Cl N3 O2'
_chemical_formula_sum            'C24 H22 Cl N3 O2'
_chemical_formula_weight         419.89
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-03-07 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                96.881(4)
_cell_angle_beta                 92.036(2)
_cell_angle_gamma                109.013(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9332(14)
_cell_length_b                   10.9116(18)
_cell_length_c                   12.9665(19)
_cell_measurement_reflns_used    3098
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1050.2(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9819
              2theta: -15.0868
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9819
              2theta: -15.0868
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9819
              2theta: -15.0868
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.098887
_diffrn_orient_matrix_UB_12      0.023691
_diffrn_orient_matrix_UB_13      -0.086883
_diffrn_orient_matrix_UB_21      0.086068
_diffrn_orient_matrix_UB_22      -0.005770
_diffrn_orient_matrix_UB_23      0.046263
_diffrn_orient_matrix_UB_31      0.014541
_diffrn_orient_matrix_UB_32      -0.075355
_diffrn_orient_matrix_UB_33      -0.013525
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13555
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             440
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0444P)^2^+0.3363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4106
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra09766b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7229661
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.960
_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. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C18') \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.02
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C19') \\sim Ueq, Uanis(C20') \\sim Ueq, Uanis(C21') \\sim Ueq,
Uanis(C22') \\sim Ueq, Uanis(C23') \\sim Ueq, Uanis(C24') \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C19')=Sof(C20')=Sof(H20')=Sof(C21')=Sof(H21')=Sof(C22')=Sof(H22')=
 Sof(C23')=Sof(H23')=Sof(C24')=Sof(H24')=1-FVAR(1)
 Sof(C18')=Sof(H18A)=Sof(H18B)=Sof(C18)=Sof(H18C)=Sof(H18D)=Sof(C19)=Sof(C20)=
 Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=
 Sof(H24)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C18'(H18A,H18B), C18(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24'), C20(H20),
  C21(H21), C22(H22), C23(H23), C24(H24)
4.c Fitted hexagon refined as free rotating group:
 C19'(C20',C21',C22',C23',C24'), C19(C20,C21,C22,C23,C24)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              73774
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'