Synthesis of 14-membered enediyne-embedded macrocycles
Glavaš, Mladena; Gredičak, Matija; Stefanic, Zoran; Jerić, Ivanka; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00090C

data_7158639
_publ_section_title
;
 Synthesis of 14-membered enediyne-embedded macrocycles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00090C
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C39 H42 N2 O4'
_chemical_formula_sum            'C39 H42 N2 O4'
_chemical_formula_weight         602.74
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-25 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.779(2)
_cell_angle_beta                 96.053(3)
_cell_angle_gamma                91.867(3)
_cell_formula_units_Z            2
_cell_length_a                   11.4922(4)
_cell_length_b                   11.9793(4)
_cell_length_c                   12.3100(4)
_cell_measurement_reflns_used    12663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8530
_cell_measurement_theta_min      3.8800
_cell_volume                     1683.34(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     10.00  36.00   1.00    1.50    --   42.00  71.00  -5.19   26
  2  \w     58.00 118.00   1.00    1.50    --   42.00  71.00  -5.19   60
  3  \w     94.00 147.00   1.00    1.50    --   74.00  73.00  26.04   53
  4  \w    109.00 145.00   1.00    1.50    --   66.00  77.00  90.42   36
  5  \w    130.00 171.00   1.00    7.50    --  111.00  77.00  30.00   41
  6  \w    146.00 173.00   1.00    7.50    --  111.00 112.00  30.00   27
  7  \w    120.00 177.00   1.00    7.50    --  111.00  77.00   0.00   57
  8  \w    147.00 175.00   1.00    7.50    --  111.00  77.00-120.00   28
  9  \w    122.00 178.00   1.00    7.50    --  111.00  77.00 -90.00   56
 10  \w    106.00 133.00   1.00    7.50    --  111.00 112.00  30.00   27
 11  \w    115.00 173.00   1.00    7.50    --  111.00  77.00  90.00   58
 12  \w    132.00 178.00   1.00    7.50    --  111.00  61.00 150.00   46
 13  \w    126.00 151.00   1.00    7.50    --  111.00  77.00 150.00   25
 14  \w    115.00 141.00   1.00    7.50    --  111.00  61.00  90.00   26
 15  \w     88.00 146.00   1.00    1.50    --   70.00  75.00  71.40   58
 16  \w     86.00 141.00   1.00    7.50    --  111.00  61.00  30.00   55
 17  \w     83.00 133.00   1.00    7.50    --  111.00  61.00   0.00   50
 18  \w     82.00 144.00   1.00    7.50    --  111.00  61.00 -60.00   62
 19  \w     77.00 103.00   1.00    7.50    --  111.00  77.00  30.00   26
 20  \w     81.00 107.00   1.00    7.50    --  111.00  61.00  60.00   26
 21  \w     81.00 107.00   1.00    7.50    --  111.00  61.00  90.00   26
 22  \w     81.00 136.00   1.00    7.50    --  111.00  61.00 120.00   55
 23  \w     82.00 107.00   1.00    7.50    --  111.00  61.00 150.00   25
 24  \w     78.00 106.00   1.00    7.50    --  111.00  77.00  90.00   28
 25  \w     78.00 178.00   1.00    7.50    --  111.00  77.00 120.00  100
 26  \w     77.00 174.00   1.00    7.50    --  111.00  77.00  60.00   97
 27  \w     83.00 154.00   1.00    7.50    --  111.00  61.00-120.00   71
 28  \w     82.00 169.00   1.00    7.50    --  111.00  61.00-180.00   87
 29  \w     77.00 113.00   1.00    7.50    --  111.00  77.00-180.00   36
 30  \w     81.00 144.00   1.00    7.50    --  111.00  61.00-150.00   63
 31  \w     77.00 103.00   1.00    7.50    --  111.00  77.00-120.00   26
 32  \w     81.00 152.00   1.00    7.50    --  111.00  61.00 -90.00   71
 33  \w     77.00 103.00   1.00    7.50    --  111.00  77.00   0.00   26
 34  \w     78.00 174.00   1.00    7.50    --  111.00  77.00 -30.00   96
 35  \w     77.00 116.00   1.00    7.50    --  111.00  77.00 150.00   39
 36  \w     37.00  71.00   1.00    1.50    --   70.00  75.00  71.40   34
 37  \w     41.00  68.00   1.00    1.50    --   74.00  73.00  26.04   27
 38  \w     45.00  70.00   1.00    7.50    --   78.00  75.00  -7.25   25
 39  \w     38.00  79.00   1.00    1.50    --   70.00  77.00 -55.78   41
 40  \w     77.00 102.00   1.00    7.50    --  111.00  77.00 -90.00   25
 41  \w     77.00 159.00   1.00    7.50    --  111.00  77.00 -60.00   82
 42  \w     77.00 157.00   1.00    7.50    --  111.00  77.00-150.00   80
 43  \w    120.00 145.00   1.00    7.50    --  111.00 -77.00-150.00   25
 44  \w     81.00 109.00   1.00    7.50    --  111.00-112.00 -90.00   28
 45  \w     52.00  78.00   1.00    7.50    --  111.00-112.00 -90.00   26
 46  \w     40.00  78.00   1.00    7.50    --  111.00 -77.00-150.00   38
 47  \w     35.00 111.00   1.00    7.50    --  111.00-112.00-150.00   76
 48  \w     40.00 115.00   1.00    7.50    --  111.00-112.00 -30.00   75
 49  \w     38.00  63.00   1.00    7.50    --  111.00-112.00 120.00   25
 50  \w     82.00 115.00   1.00    7.50    --  111.00-112.00 120.00   33
 51  \w     38.00  85.00   1.00    7.50    --  111.00 -95.00 150.00   47
 52  \w     37.00 130.00   1.00    7.50    --  111.00 -61.00   0.00   93
 53  \w     35.00  72.00   1.00    1.50    --   66.00  77.00  90.42   37
 54  \w     32.00  76.00   1.00    1.50    --   66.00  77.00 137.41   44
 55  \w     19.00  44.00   1.00    1.50    --   54.00  81.00  90.32   25
 56  \w      9.00  42.00   1.00    1.50    --   42.00  79.00 130.61   33
 57  \w     10.00  35.00   1.00    1.50    --   46.00  84.00  39.32   25
 58  \w     19.00  44.00   1.00    1.50    --   54.00  82.00   3.06   25
 59  \w     29.00  54.00   1.00    1.50    --   62.00  75.00 -67.86   25
 60  \w     27.00  55.00   1.00    1.50    --   58.00  76.00-107.11   28
 61  \w     29.00  71.00   1.00    1.50    --   62.00  76.00-145.21   42
 62  \w     33.00  65.00   1.00    1.50    --   66.00  75.00-170.54   32
 63  \w      3.00  28.00   1.00    1.50    --   42.00  91.00-155.60   25
 64  \w    -71.00 -33.00   1.00    1.50    --  -40.62 -38.00   0.00   38
 65  \w    -65.00  34.00   1.00    1.50    --  -40.62  38.00 150.00   99
 66  \w      4.00  81.00   1.00    1.50    --   40.62-126.00  60.00   77
 67  \w     33.00 109.00   1.00    7.50    --  111.00 -95.00   0.00   76
 68  \w      6.00  99.00   1.00    1.50    --   40.62-126.00-120.00   93
 69  \w   -116.00 -91.00   1.00    1.50    --  -40.62 -38.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0488169000
_diffrn_orient_matrix_UB_12      0.0811690000
_diffrn_orient_matrix_UB_13      0.0946248000
_diffrn_orient_matrix_UB_21      0.0291430000
_diffrn_orient_matrix_UB_22      0.0875807000
_diffrn_orient_matrix_UB_23      -0.0830245000
_diffrn_orient_matrix_UB_31      -0.1223252000
_diffrn_orient_matrix_UB_32      0.0481366000
_diffrn_orient_matrix_UB_33      0.0031845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33048
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.986
_diffrn_reflns_theta_min         3.694
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 4264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         12807
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0749
_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^)+(0.1557P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2022
_refine_ls_wR_factor_ref         0.2190
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                11452
_reflns_number_total             12807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00090c2.cif
_cod_data_source_block           m-332g
_cod_database_code               7158639
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C39H42N2O4
_chemical_oxdiff_usercomment
'odrediti apsolutnu konfiguraciju, 1 kiralni centar poznat'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Ternary CH refined with riding coordinates:
 C1(H1), C16(H16), C1A(H1AA), C16A(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C14(H14A,H14B), C28(H28A,H28B), C33(H33A,H33B),
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C14A(H14C,H14D), C28A(H28C,H28D), C33A(H33C,
 H33D)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), N1(H1A), C7A(H7A),
 C8A(H8A), C9A(H9A), C10A(H10A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A),
  C23A(H23A), C35A(H35A), C36A(H36A), C37A(H37A), C38A(H38A), C39A(H39A),
 N1A(H1AB)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C26A(H26D,H26E,H26F), C27A(H27D,H27E,H27F),
 C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F)
;
_shelx_res_checksum              94722
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.766
_oxdiff_exptl_absorpt_empirical_full_min 0.483