# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b1_a
_database_code_depnum_ccdc_archive 'CCDC 2069587'
loop_
_audit_author_name
_audit_author_address
'Ji-Eun Lee'
;Gyeongsang National University
South Korea
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Miharadiene C'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N O4'
_chemical_formula_weight         345.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4522(11)
_cell_length_b                   17.5351(16)
_cell_length_c                   10.6630(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.859(6)
_cell_angle_gamma                90
_cell_volume                     1889.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3600
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.89

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SHELXL-2014/7 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15885
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4685
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0738P)²+0.6511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4685
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1778
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47765(15) 0.08960(8) 0.53801(16) 0.0417(4) Uani 1 1 d . . . . .
O2 O 0.36792(16) -0.01236(8) 0.57847(17) 0.0471(4) Uani 1 1 d . . . . .
H1 H 0.4215 -0.0341 0.5434 0.071 Uiso 1 1 calc R U . . .
O3 O 0.66863(14) 0.35916(8) 0.65174(14) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.63593(14) 0.24650(8) 0.53042(14) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.38650(17) 0.22801(10) 0.58598(18) 0.0362(4) Uani 1 1 d . . . . .
H1A H 0.4413 0.2023 0.5515 0.043 Uiso 1 1 calc R U . . .
C1 C 0.3028(2) 0.10656(12) 0.6421(2) 0.0338(5) Uani 1 1 d . . . . .
C2 C 0.2162(2) 0.06763(14) 0.7013(2) 0.0437(6) Uani 1 1 d . . . . .
H2A H 0.2179 0.0135 0.7039 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1290(2) 0.10604(15) 0.7556(3) 0.0509(6) Uani 1 1 d . . . . .
H3A H 0.0720 0.0790 0.7965 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1258(2) 0.18489(15) 0.7495(2) 0.0480(6) Uani 1 1 d . . . . .
H4A H 0.0645 0.2118 0.7852 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2089(2) 0.22519(13) 0.6933(2) 0.0411(5) Uani 1 1 d . . . . .
H5A H 0.2041 0.2793 0.6909 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3020(2) 0.18765(12) 0.6386(2) 0.0342(5) Uani 1 1 d . . . . .
C7 C 0.3901(2) 0.06186(12) 0.5830(2) 0.0341(5) Uani 1 1 d . . . . .
C8 C 0.3925(2) 0.31116(12) 0.5828(2) 0.0351(5) Uani 1 1 d . . . . .
H8A H 0.3000 0.3314 0.5558 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4612(2) 0.34551(12) 0.7146(2) 0.0373(5) Uani 1 1 d . . . . .
H9A H 0.4460 0.4013 0.7123 0.045 Uiso 1 1 calc R U . . .
H9B H 0.4225 0.3235 0.7821 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6075(2) 0.32989(13) 0.7487(2) 0.0359(5) Uani 1 1 d . . . . .
H10A H 0.6495 0.3537 0.8335 0.043 Uiso 1 1 calc R U . . .
H10B H 0.6225 0.2742 0.7575 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6153(2) 0.32722(12) 0.5271(2) 0.0339(5) Uani 1 1 d . . . . .
C12 C 0.4663(2) 0.33701(12) 0.4831(2) 0.0371(5) Uani 1 1 d . . . . .
H12A H 0.4324 0.3076 0.4020 0.045 Uiso 1 1 calc R U . . .
H12B H 0.4462 0.3915 0.4628 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7669(2) 0.21991(14) 0.5874(2) 0.0474(6) Uani 1 1 d . . . . .
H13A H 0.7684 0.1641 0.5839 0.071 Uiso 1 1 calc R U . . .
H13B H 0.8274 0.2407 0.5394 0.071 Uiso 1 1 calc R U . . .
H13C H 0.7949 0.2367 0.6780 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6868(3) 0.36546(12) 0.4362(2) 0.0431(6) Uani 1 1 d . . . . .
H14A H 0.7799 0.3479 0.4597 0.052 Uiso 1 1 calc R U . . .
H14B H 0.6459 0.3477 0.3468 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6863(3) 0.45218(13) 0.4361(3) 0.0508(7) Uani 1 1 d . . . . .
H15A H 0.5947 0.4709 0.4251 0.061 Uiso 1 1 calc R U . . .
H15B H 0.7408 0.4711 0.5204 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7404(2) 0.48269(14) 0.3284(3) 0.0491(6) Uani 1 1 d . . . . .
H16A H 0.6960 0.4669 0.2432 0.059 Uiso 1 1 calc R U . . .
C17 C 0.8412(2) 0.52830(13) 0.3380(3) 0.0457(6) Uani 1 1 d . . . . .
H17A H 0.8874 0.5443 0.4226 0.055 Uiso 1 1 calc R U . . .
C18 C 0.8882(2) 0.55636(13) 0.2305(2) 0.0452(6) Uani 1 1 d . . . . .
H18A H 0.8414 0.5391 0.1468 0.054 Uiso 1 1 calc R U . . .
C19 C 0.9871(2) 0.60249(14) 0.2341(3) 0.0544(7) Uani 1 1 d . . . . .
H19A H 1.0350 0.6203 0.3170 0.065 Uiso 1 1 calc R U . . .
C20 C 1.0313(3) 0.62963(16) 0.1197(3) 0.0584(7) Uani 1 1 d . . . . .
H20A H 1.1075 0.6637 0.1488 0.088 Uiso 1 1 calc R U . . .
H20B H 1.0567 0.5858 0.0744 0.088 Uiso 1 1 calc R U . . .
H20C H 0.9588 0.6572 0.0606 0.088 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.237(2) . ?
O2 C7 1.321(2) . ?
O2 H1 0.8400 . ?
O3 C11 1.418(3) . ?
O3 C10 1.442(2) . ?
O4 C13 1.426(3) . ?
O4 C11 1.431(2) . ?
N1 C6 1.360(3) . ?
N1 C8 1.460(3) . ?
N1 H1A 0.8800 . ?
C1 C2 1.406(3) . ?
C1 C6 1.422(3) . ?
C1 C7 1.463(3) . ?
C2 C3 1.374(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.418(3) . ?
C5 H5A 0.9500 . ?
C8 C9 1.528(3) . ?
C8 C12 1.534(3) . ?
C8 H8A 1.0000 . ?
C9 C10 1.503(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(3) . ?
C11 C14 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.502(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.306(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.445(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.305(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.489(3) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H1 109.5 . . ?
C11 O3 C10 113.05(15) . . ?
C13 O4 C11 117.12(17) . . ?
C6 N1 C8 124.45(16) . . ?
C6 N1 H1A 117.8 . . ?
C8 N1 H1A 117.8 . . ?
C2 C1 C6 119.83(19) . . ?
C2 C1 C7 118.56(19) . . ?
C6 C1 C7 121.60(18) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 H2A 119.2 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
N1 C6 C5 120.97(19) . . ?
N1 C6 C1 122.11(18) . . ?
C5 C6 C1 116.92(19) . . ?
O1 C7 O2 120.90(19) . . ?
O1 C7 C1 124.20(19) . . ?
O2 C7 C1 114.89(18) . . ?
N1 C8 C9 112.65(18) . . ?
N1 C8 C12 110.09(16) . . ?
C9 C8 C12 108.65(17) . . ?
N1 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C12 C8 H8A 108.5 . . ?
C10 C9 C8 111.10(17) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 C9 111.82(18) . . ?
O3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
O3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 O4 110.32(17) . . ?
O3 C11 C12 111.78(16) . . ?
O4 C11 C12 104.82(17) . . ?
O3 C11 C14 106.47(17) . . ?
O4 C11 C14 110.85(16) . . ?
C12 C11 C14 112.67(19) . . ?
C11 C12 C8 114.26(18) . . ?
C11 C12 H12A 108.7 . . ?
C8 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C8 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 116.04(18) . . ?
C15 C14 H14A 108.3 . . ?
C11 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 110.79(19) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 127.8(3) . . ?
C17 C16 H16A 116.1 . . ?
C15 C16 H16A 116.1 . . ?
C16 C17 C18 125.3(3) . . ?
C16 C17 H17A 117.3 . . ?
C18 C17 H17A 117.3 . . ?
C19 C18 C17 128.0(3) . . ?
C19 C18 H18A 116.0 . . ?
C17 C18 H18A 116.0 . . ?
C18 C19 C20 125.7(3) . . ?
C18 C19 H19A 117.2 . . ?
C20 C19 H19A 117.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        Streptomyces
