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

data_7158638
_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         'C32 H38 N2 O3'
_chemical_formula_sum            'C32 H38 N2 O3'
_chemical_formula_weight         498.64
_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   mixed
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8525(2)
_cell_length_b                   13.9095(4)
_cell_length_c                   34.5620(8)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3170
_cell_measurement_theta_min      3.4170
_cell_volume                     2813.53(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.993
_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   -111.00 -36.00   1.00   15.00    --  -40.99 -38.00   0.00   75
  2  \w     41.00  68.00   1.00   15.00    --   40.99 -77.00 150.00   27
  3  \w    -23.00  69.00   1.00   15.00    --   40.99 -57.00   0.00   92
  4  \w    148.00 174.00   1.00   60.00    --  111.00  30.00  90.00   26
  5  \w     80.00 148.00   1.00   60.00    --  111.00 111.00   0.00   68
  6  \w     84.00 132.00   1.00   60.00    --  111.00 -74.00 -29.00   48
  7  \w     83.00 153.00   1.00   60.00    --  111.00  45.00 -30.00   70
  8  \w     39.00  81.00   1.00   60.00    --  111.00 -45.00  30.00   42
  9  \w     94.00 130.00   1.00   60.00    --  111.00 -45.00  30.00   36
 10  \w     84.00 177.00   1.00   60.00    --  111.00  45.00 -60.00   93
 11  \w    140.00 178.00   1.00   60.00    --  111.00  45.00-120.00   38
 12  \w     81.00 177.00   1.00   60.00    --  111.00  61.00-150.00   96
 13  \w     55.00  81.00   1.00   60.00    --  111.00-111.00   0.00   26
 14  \w     33.00  99.00   1.00   60.00    --  111.00-111.00 -60.00   66
;
_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      -0.1768908000
_diffrn_orient_matrix_UB_12      0.0819253000
_diffrn_orient_matrix_UB_13      0.0014218000
_diffrn_orient_matrix_UB_21      -0.1212469000
_diffrn_orient_matrix_UB_22      -0.0500322000
_diffrn_orient_matrix_UB_23      0.0340515000
_diffrn_orient_matrix_UB_31      0.1525673000
_diffrn_orient_matrix_UB_32      0.0552467000
_diffrn_orient_matrix_UB_33      0.0287383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            13625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.984
_diffrn_reflns_theta_min         3.425
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0311P)^2^+0.1182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4504
_reflns_number_total             5803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00090c2.cif
_cod_data_source_block           m404_1
_cod_database_code               7158638
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C32 H38 N2 O3'
_chemical_oxdiff_usercomment
'ponovljeno snimanje istog kristala jer se pomicao'
_reflns_odcompleteness_completeness 99.94
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C17(H17A,H17B), C2(H2A,H2B), C3(H3A,H3B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C10(H10), C19(H19), C22(H22), C8(H8), C7(H7), C20(H20), C21(H21),
 C9(H9)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C), C31(H31A,H31B,H31C)
;
_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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.492