Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center
Chen, Bo; Chu, Wen-Dao; Liu, Quan-Zhong; RSC Advances 9 (2019) 1487–; doi:10.1039/C8RA08909D

data_7232166
_publ_section_title
;
 Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes
 with diazo esters: facile approaches to dihydropyrazoles containing a
 quaternary center
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1487
_journal_paper_doi               10.1039/C8RA08909D
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C25 H21 Cl N2 O3'
_chemical_formula_sum            'C25 H21 Cl N2 O3'
_chemical_formula_weight         432.89
_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
_audit_creation_date             2018-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2018-05-02 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                88.684(12)
_cell_angle_beta                 79.885(12)
_cell_angle_gamma                89.121(14)
_cell_formula_units_Z            2
_cell_length_a                   6.3041(16)
_cell_length_b                   12.0699(17)
_cell_length_c                   14.252(3)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.77
_cell_measurement_theta_min      3.15
_cell_volume                     1067.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26074
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.574
_diffrn_reflns_theta_min         3.150
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  0.734
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       rod
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.734
_exptl_transmission_factor_min   0.688
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0582
_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/[\s^2^(Fo^2^)+(0.0651P)^2^+0.8943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3299
_reflns_number_total             4160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra08909d2.cif
_cod_data_source_block           cu_20180402l_0m-auto
_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               7232166
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'