Access to arylurazoles bearing both central and C-N axial chirality via asymmetric desymmetrization catalyzed by chiral phosphoric acid
Wu, Wenhui; Li, Wenkai; Xu, Yongqiang; Zhou, Yuhan; Qu, Jingping; Wang, Baomin; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00223D

data_7161102
_publ_section_title
;
 Access to arylurazoles bearing both central and C-N axial chirality
 <i>via</i> asymmetric desymmetrization catalyzed by chiral phosphoric
 acid.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3454
_journal_page_last               3458
_journal_paper_doi               10.1039/d6ob00223d
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C34 H31 Cl N5 O3'
_chemical_formula_sum            'C34 H31 Cl N5 O3'
_chemical_formula_weight         593.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2qsz7r
_audit_creation_date             2026-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-02-26 deposited with the CCDC.	2026-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.342(3)
_cell_angle_beta                 91.011(4)
_cell_angle_gamma                97.382(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5157(11)
_cell_length_b                   12.5173(16)
_cell_length_c                   13.9114(17)
_cell_measurement_reflns_used    8079
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.19
_cell_volume                     1470.3(3)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27868
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.543
_diffrn_reflns_theta_min         2.190
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6045
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1558 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.8110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             622
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0698P)^2^+0.7495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4326
_reflns_number_total             6038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00223d2.cif
_cod_data_source_block           aa
_cod_depositor_comments          'Adding full bibliography for 7161102.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7161102
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.983
_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 Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), N007(H007), C00K(H00K), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C014(H014),
 C015(H015), C016(H016)
2.c Idealised Me refined as rotating group:
 C00X(H00C,H00D,H00E), C013(H01A,H01B,H01C), C017(H01D,H01E,H01F)
;
_shelx_res_checksum              46495
_olex2_submission_special_instructions 'No special instructions were received'