A chiroptical approach for the absolute stereochemical determination of <i>P</i>-stereogenic centers.
Chakraborty, Debarshi; Gholami, Hadi; Sarkar, Aritra; Joyce, Leo A.; Jackson, James E.; Borhan, Babak; Chemical science 12 (2020) 1750–1755; doi:10.1039/d0sc02940h

data_1559731
_publ_section_title
;
 A chiroptical approach for the absolute stereochemical determination of
 <i>P</i>-stereogenic centers.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1750
_journal_page_last               1755
_journal_paper_doi               10.1039/d0sc02940h
_journal_volume                  12
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C54 H43 N4 O P Zn, 0.17(C7 H8)'
_chemical_formula_sum            'C55.17 H44.33 N4 O P Zn'
_chemical_formula_weight         875.62
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-26
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2020-05-23 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   28.1290(8)
_cell_length_b                   28.1290(8)
_cell_length_c                   10.2773(4)
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.27
_cell_measurement_theta_min      3.14
_cell_volume                     7042.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2745
_diffrn_reflns_av_unetI/netI     0.2483
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21473
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_min         1.813
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.376
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0778 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.7866. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            purple
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       needle
_exptl_crystal_F_000             2738
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         8298
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1980
_refine_ls_R_factor_gt           0.0880
_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^)+(0.1014P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2611
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3791
_reflns_number_total             8298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02940h2.cif
_cod_data_source_block           bb417b
_cod_depositor_comments
;Adding full bibliography for 1559731.cif.

 Adding full bibliography for 1559731.cif.
;
_cod_original_cell_volume        7042.4(5)
_cod_database_code               1559731
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.589
_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. Restrained distances
 C2S-C1S
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C3S \\sim C2S \\sim C7S \\sim C6S \\sim C5S \\sim C4S: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.004
Uanis(C34) = Uanis(C7)
Uanis(C8) = Uanis(C35)
4. Others
 Fixed Sof: C1S(0.16667) H1SA(0.16667) H1SB(0.16667) H1SC(0.16667)
 C3S(0.16667) H3S(0.16667) C2S(0.16667) C7S(0.16667) H7S(0.16667) C6S(0.16667)
 H6S(0.16667) C5S(0.16667) H5S(0.16667) C4S(0.16667) H4S(0.16667)
5.a Riding coordinates:
 C1S(H1SA,H1SB,H1SC)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C7(H7), C45(H45), C50(H50), C8(H8), C41(H41), C54(H54), C48(H48),
 C28(H28), C39(H39), C52(H52), C12(H12), C33(H33), C13(H13), C51(H51), C42(H42),
  C44(H44), C34(H34), C17(H17), C18(H18), C38(H38), C40(H40), C9(H9), C22(H22),
 C53(H53), C36(H36), C10(H10), C6(H6), C46(H46), C32(H32), C23(H23), C27(H27),
 C47(H47), C3S(H3S), C7S(H7S), C6S(H6S), C5S(H5S), C4S(H4S)
5.d Fitted hexagon refined as free rotating group:
 C3S(C2S,C7S,C6S,C5S,C4S)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id DC-102
_olex2_submission_special_instructions 'No special instructions were received'