Asymmetric synthesis of planar-chiral macrocycles via organocatalyzed enantioselective macrocyclization
Yu, Shaoze; Shen, Guosong; He, Faqian; Yang, Xiaoyu; Chemical Communications  (2022) –; doi:10.1039/D2CC01690G

data_7130219
_publ_section_title
;
 Asymmetric synthesis of planar-chiral macrocycles via organocatalyzed
 enantioselective macrocyclization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01690G
_journal_year                    2022
_chemical_formula_moiety         'C42 H49 N O3'
_chemical_formula_sum            'C42 H49 N O3'
_chemical_formula_weight         615.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9530(2)
_cell_length_b                   11.3417(2)
_cell_length_c                   28.7781(5)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    150
_cell_measurement_theta_max      79.38
_cell_measurement_theta_min      3.07
_cell_volume                     3574.98(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            72241
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.463
_diffrn_reflns_theta_min         3.071
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1271 before and 0.0513 after correction.
The Ratio of minimum to maximum transmission is 0.8861.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 3288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         7699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0372P)^2^+0.4945P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7602
_reflns_number_total             7699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01690g2.cif
_cod_data_source_block           cu_yxy_0507_0m
_cod_database_code               7130219
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.875
_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:
 C00G(H00A,H00B), C00P(H00G,H00I), C00R(H00L,H00M), C00S(H00N,H00P), C00V(H00V,
 H00W), C00X(H00Z,HA), C014(H01D,H01E), C016(H01F,H01G), C019(H01K,H01L),
 C01A(H01M,H01N)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C00C(H00C), C00H(H00H), C00J(H00J), C00K(H00K), C00O(H00O),
 C00Q(H00Q), C00U(H00U), C00Y(H00), C00Z(H0AA), C010(H010), C011(H011),
 C013(H013), C017(H017)
2.c Idealised Me refined as rotating group:
 C00L(H00D,H00E,H00F), C00T(H00R,H00S,H00T), C00W(H00X,H00Y,H), C012(H01A,H01B,
 H01C), C018(H01H,H01I,H01J)
;
_shelx_res_checksum              58101
_shelx_hkl_checksum              9223
_olex2_submission_special_instructions 'No special instructions were received'