Atroposelective Synthesis of Barbiturate Substituted Chiral Styrenes
Devi, Manju; Jain, Gyanshree; Gupta, Navya; Ansari, Najmuddin; Singh, Ravi Prakash; Chemical Communications  (2026) –; doi:10.1039/D5CC06302G

data_7135313
_publ_section_title
;
 Atroposelective Synthesis of Barbiturate Substituted Chiral Styrenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06302G
_journal_year                    2026
_chemical_formula_moiety         '0.087(C43 H35 N2 O5 P), 0.087[C4O2H8]'
_chemical_formula_sum            'C4.09 H3.74 N0.17 O0.61 P0.09'
_chemical_formula_weight         67.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-10-30
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-10-31 deposited with the CCDC.	2025-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.883(2)
_cell_angle_gamma                90
_cell_formula_units_Z            46
_cell_length_a                   19.0074(6)
_cell_length_b                   11.0694(6)
_cell_length_c                   18.0225(8)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.63
_cell_volume                     3542.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      305.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            76660
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         3.630
_exptl_absorpt_coefficient_mu    0.140
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1639
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3121 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         8671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.4367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                7421
_reflns_number_total             8671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06302g2.cif
_cod_data_source_block           123_0ma_a
_cod_database_code               7135313
_shelx_shelxl_version_number     2019/1
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C22(H22),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C40(H40),
 C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 20 electrons were 
found in a volume of 124\%A^3^ in 3 voids per unit cell. 
This is consistent with the presence of 
0.087[C4O2H8] per Asymmetric Unit 
which account for 192 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              21989
_shelx_fab_checksum              23272
_olex2_submission_special_instructions 'No special instructions were received'