data_sf20180619-wcs
_audit_creation_date               2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number       '2017/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C27 H26 O4'
_chemical_formula_sum              'C27 H26 O4'
_chemical_formula_weight           414.48
_chemical_absolute_configuration   rmad
_chemical_melting_point            ?
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'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             43
_space_group_name_H-M_alt          'F d d 2'
_space_group_name_Hall             'F 2 -2d'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z'
 'x+1/4, -y+1/4, z+1/4'
 '-x+1/4, y+1/4, z+1/4'
 'x, y+1/2, z+1/2'
 '-x, -y+1/2, z+1/2'
 'x+1/4, -y+3/4, z+3/4'
 '-x+1/4, y+3/4, z+3/4'
 'x+1/2, y, z+1/2'
 '-x+1/2, -y, z+1/2'
 'x+3/4, -y+1/4, z+3/4'
 '-x+3/4, y+1/4, z+3/4'
 'x+1/2, y+1/2, z'
 '-x+1/2, -y+1/2, z'
 'x+3/4, -y+3/4, z+1/4'
 '-x+3/4, y+3/4, z+1/4'

_cell_length_a                     23.367(12)
_cell_length_b                     70.70(4)
_cell_length_c                     5.211(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       8609(8)
_cell_formula_units_Z              16
_cell_measurement_reflns_used      1187
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        19.09
_cell_measurement_theta_min        2.45
_shelx_estimated_absorpt_T_max     0.992
_shelx_estimated_absorpt_T_min     0.935
_exptl_absorpt_coefficient_mu      0.085
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.5859
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0826 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.7858. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.279
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               3520
_exptl_crystal_size_max            0.8
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0985
_diffrn_reflns_av_unetI/netI       0.1446
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         27
_diffrn_reflns_limit_h_min         -30
_diffrn_reflns_limit_k_max         64
_diffrn_reflns_limit_k_min         -90
_diffrn_reflns_limit_l_max         6
_diffrn_reflns_limit_l_min         -6
_diffrn_reflns_number              13131
_diffrn_reflns_point_group_measured_fraction_full  0.991
_diffrn_reflns_point_group_measured_fraction_max  0.981
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.560
_diffrn_reflns_theta_min           2.890
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.775
_reflns_Friedel_fraction_full      0.981
_reflns_Friedel_fraction_max       0.963
_reflns_number_gt                  2018
_reflns_number_total               4882
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.35A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.35A (?, 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)'
_refine_diff_density_max           0.151
_refine_diff_density_min           -0.138
_refine_diff_density_rms           0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -1.5(10)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.954
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       283
_refine_ls_number_reflns           4882
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.1943
_refine_ls_R_factor_gt             0.0641
_refine_ls_restrained_S_all        0.954
_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/[σ²(Fo²)+(0.0448P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1052
_refine_ls_wR_factor_ref           0.1406
_refine_special_details            ?
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C15(H15), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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 0.86803(16) 0.28793(5) 0.6749(8) 0.0659(12) Uani 1 1 d . . . . .
 O2 O 0.84697(14) 0.29675(5) 0.2571(7) 0.0514(10) Uani 1 1 d . . . . .
 O3 O 0.84500(17) 0.36017(5) -0.0384(9) 0.0653(12) Uani 1 1 d . . . . .
 O4 O 0.76944(17) 0.36993(5) 0.2940(9) 0.0739(13) Uani 1 1 d . . . . .
 C1 C 0.8335(2) 0.28354(7) 0.4530(13) 0.0540(16) Uani 1 1 d . . . . .
 C2 C 0.8565(2) 0.26488(8) 0.3658(12) 0.0504(16) Uani 1 1 d . . . . .
 C3 C 0.8359(3) 0.25341(8) 0.1757(13) 0.0651(19) Uani 1 1 d . . . . .
 H3 H 0.802777 0.256453 0.086156 0.078 Uiso 1 1 calc R . . . .
 C4 C 0.8664(3) 0.23706(9) 0.1218(14) 0.076(2) Uani 1 1 d . . . . .
 H4 H 0.853034 0.228751 -0.002891 0.091 Uiso 1 1 calc R . . . .
 C5 C 0.9161(3) 0.23304(9) 0.2512(15) 0.074(2) Uani 1 1 d . . . . .
 H5 H 0.936685 0.222229 0.208436 0.089 Uiso 1 1 calc R . . . .
 C6 C 0.9358(3) 0.24444(9) 0.4390(15) 0.073(2) Uani 1 1 d . . . . .
 H6 H 0.969190 0.241506 0.527338 0.087 Uiso 1 1 calc R . . . .
 C7 C 0.9051(3) 0.26061(8) 0.4973(13) 0.0573(16) Uani 1 1 d . . . . .
 C8 C 0.9165(2) 0.27545(8) 0.6879(14) 0.0678(19) Uani 1 1 d . . . . .
 H8A H 0.920044 0.270049 0.858267 0.081 Uiso 1 1 calc R . . . .
 H8B H 0.951470 0.282170 0.646812 0.081 Uiso 1 1 calc R . . . .
 C9 C 0.7729(2) 0.28487(7) 0.5275(13) 0.0572(17) Uani 1 1 d . . . . .
 H9A H 0.764920 0.275460 0.658126 0.069 Uiso 1 1 calc R . . . .
 H9B H 0.749210 0.282034 0.379610 0.069 Uiso 1 1 calc R . . . .
 C10 C 0.7568(2) 0.30443(7) 0.6307(11) 0.0512(16) Uani 1 1 d . . . . .
 H10 H 0.774622 0.305998 0.799701 0.061 Uiso 1 1 calc R . . . .
 C11 C 0.7816(2) 0.31911(7) 0.4518(11) 0.0457(14) Uani 1 1 d . . . . .
 C12 C 0.7628(2) 0.33789(8) 0.4583(12) 0.0518(15) Uani 1 1 d . . . . .
 H12 H 0.734639 0.341375 0.575436 0.062 Uiso 1 1 calc R . . . .
 C13 C 0.7849(2) 0.35127(7) 0.2954(13) 0.0512(15) Uani 1 1 d . . . . .
 C14 C 0.8267(2) 0.34614(8) 0.1175(12) 0.0495(16) Uani 1 1 d . . . . .
 C15 C 0.8460(2) 0.32777(7) 0.1106(11) 0.0475(15) Uani 1 1 d . . . . .
 H15 H 0.873975 0.324205 -0.006738 0.057 Uiso 1 1 calc R . . . .
 C16 C 0.8236(2) 0.31470(7) 0.2788(11) 0.0439(14) Uani 1 1 d . . . . .
 C17 C 0.8881(2) 0.35560(8) -0.2213(13) 0.0715(19) Uani 1 1 d . . . . .
 H17A H 0.874755 0.345605 -0.330585 0.107 Uiso 1 1 calc GR . . . .
 H17B H 0.922103 0.351549 -0.133302 0.107 Uiso 1 1 calc GR . . . .
 H17C H 0.896660 0.366554 -0.323127 0.107 Uiso 1 1 calc GR . . . .
 C18 C 0.7381(3) 0.37643(9) 0.5092(15) 0.093(2) Uani 1 1 d . . . . .
 H18A H 0.732777 0.389859 0.496518 0.140 Uiso 1 1 calc GR . . . .
 H18B H 0.758754 0.373532 0.663429 0.140 Uiso 1 1 calc GR . . . .
 H18C H 0.701432 0.370295 0.513408 0.140 Uiso 1 1 calc GR . . . .
 C19 C 0.6940(2) 0.30662(7) 0.6605(12) 0.0505(16) Uani 1 1 d . . . . .
 H19 H 0.671553 0.303033 0.521410 0.061 Uiso 1 1 calc R . . . .
 C20 C 0.6670(2) 0.31307(7) 0.8621(12) 0.0535(16) Uani 1 1 d . . . . .
 H20 H 0.689614 0.316592 1.000916 0.064 Uiso 1 1 calc R . . . .
 C21 C 0.6046(2) 0.31541(8) 0.8945(12) 0.0503(15) Uani 1 1 d . . . . .
 C22 C 0.5673(3) 0.30458(8) 0.7498(14) 0.0719(19) Uani 1 1 d . . . . .
 H22 H 0.582433 0.296028 0.632388 0.086 Uiso 1 1 calc R . . . .
 C23 C 0.5090(3) 0.30595(10) 0.7724(16) 0.077(2) Uani 1 1 d . . . . .
 H23 H 0.484771 0.298632 0.671394 0.092 Uiso 1 1 calc R . . . .
 C24 C 0.4876(3) 0.31844(11) 0.9485(17) 0.086(2) Uani 1 1 d . . . . .
 H24 H 0.448173 0.319430 0.970354 0.103 Uiso 1 1 calc R . . . .
 C25 C 0.5226(3) 0.32932(9) 1.0905(14) 0.074(2) Uani 1 1 d . . . . .
 H25 H 0.506899 0.337682 1.208890 0.089 Uiso 1 1 calc R . . . .
 C26 C 0.5817(3) 0.32838(8) 1.0649(13) 0.0601(17) Uani 1 1 d . . . . .
 C27 C 0.6177(3) 0.34108(8) 1.2267(15) 0.082(2) Uani 1 1 d . . . . .
 H27A H 0.638141 0.333673 1.350784 0.123 Uiso 1 1 calc GR . . . .
 H27B H 0.593612 0.350031 1.313704 0.123 Uiso 1 1 calc GR . . . .
 H27C H 0.644415 0.347721 1.119731 0.123 Uiso 1 1 calc GR . . . .


_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 C1 1.444(7) . ?
 O1 C8 1.437(6) . ?
 O2 C1 1.419(6) . ?
 O2 C16 1.386(5) . ?
 O3 C14 1.352(6) . ?
 O3 C17 1.424(6) . ?
 O4 C13 1.368(6) . ?
 O4 C18 1.416(8) . ?
 C1 C2 1.495(7) . ?
 C1 C9 1.471(7) . ?
 C2 C3 1.368(8) . ?
 C2 C7 1.359(7) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.386(8) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.373(8) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.349(8) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.383(8) . ?
 C7 C8 1.469(8) . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C9 C10 1.530(7) . ?
 C10 H10 0.9800 . ?
 C10 C11 1.511(7) . ?
 C10 C19 1.484(7) . ?
 C11 C12 1.399(7) . ?
 C11 C16 1.369(7) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.373(7) . ?
 C13 C14 1.394(7) . ?
 C14 C15 1.376(7) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.377(7) . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 0.9600 . ?
 C19 H19 0.9300 . ?
 C19 C20 1.308(7) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.477(7) . ?
 C21 C22 1.383(7) . ?
 C21 C26 1.384(7) . ?
 C22 H22 0.9300 . ?
 C22 C23 1.372(8) . ?
 C23 H23 0.9300 . ?
 C23 C24 1.368(9) . ?
 C24 H24 0.9300 . ?
 C24 C25 1.346(9) . ?
 C25 H25 0.9300 . ?
 C25 C26 1.387(7) . ?
 C26 C27 1.492(8) . ?
 C27 H27A 0.9600 . ?
 C27 H27B 0.9600 . ?
 C27 H27C 0.9600 . ?

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
 C8 O1 C1 110.2(4) . . ?
 C16 O2 C1 117.2(4) . . ?
 C14 O3 C17 117.4(4) . . ?
 C13 O4 C18 116.5(5) . . ?
 O1 C1 C2 103.4(5) . . ?
 O1 C1 C9 108.2(5) . . ?
 O2 C1 O1 108.1(4) . . ?
 O2 C1 C2 106.4(5) . . ?
 O2 C1 C9 111.2(5) . . ?
 C9 C1 C2 118.9(5) . . ?
 C3 C2 C1 128.1(6) . . ?
 C7 C2 C1 110.1(6) . . ?
 C7 C2 C3 121.8(5) . . ?
 C2 C3 H3 121.3 . . ?
 C2 C3 C4 117.4(6) . . ?
 C4 C3 H3 121.3 . . ?
 C3 C4 H4 119.8 . . ?
 C5 C4 C3 120.5(7) . . ?
 C5 C4 H4 119.8 . . ?
 C4 C5 H5 119.3 . . ?
 C6 C5 C4 121.4(6) . . ?
 C6 C5 H5 119.3 . . ?
 C5 C6 H6 120.8 . . ?
 C5 C6 C7 118.5(7) . . ?
 C7 C6 H6 120.8 . . ?
 C2 C7 C6 120.4(6) . . ?
 C2 C7 C8 109.5(5) . . ?
 C6 C7 C8 130.2(7) . . ?
 O1 C8 C7 105.3(5) . . ?
 O1 C8 H8A 110.7 . . ?
 O1 C8 H8B 110.7 . . ?
 C7 C8 H8A 110.7 . . ?
 C7 C8 H8B 110.7 . . ?
 H8A C8 H8B 108.8 . . ?
 C1 C9 H9A 109.0 . . ?
 C1 C9 H9B 109.0 . . ?
 C1 C9 C10 112.8(4) . . ?
 H9A C9 H9B 107.8 . . ?
 C10 C9 H9A 109.0 . . ?
 C10 C9 H9B 109.0 . . ?
 C9 C10 H10 108.3 . . ?
 C11 C10 C9 108.1(4) . . ?
 C11 C10 H10 108.3 . . ?
 C19 C10 C9 111.9(4) . . ?
 C19 C10 H10 108.3 . . ?
 C19 C10 C11 111.8(4) . . ?
 C12 C11 C10 121.1(5) . . ?
 C16 C11 C10 121.6(5) . . ?
 C16 C11 C12 117.3(5) . . ?
 C11 C12 H12 119.3 . . ?
 C13 C12 C11 121.3(5) . . ?
 C13 C12 H12 119.3 . . ?
 O4 C13 C12 124.6(6) . . ?
 O4 C13 C14 115.6(6) . . ?
 C12 C13 C14 119.7(5) . . ?
 O3 C14 C13 115.5(5) . . ?
 O3 C14 C15 125.0(6) . . ?
 C15 C14 C13 119.5(6) . . ?
 C14 C15 H15 120.2 . . ?
 C14 C15 C16 119.5(5) . . ?
 C16 C15 H15 120.2 . . ?
 C11 C16 O2 123.0(5) . . ?
 C11 C16 C15 122.6(5) . . ?
 C15 C16 O2 114.4(5) . . ?
 O3 C17 H17A 109.5 . . ?
 O3 C17 H17B 109.5 . . ?
 O3 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 O4 C18 H18A 109.5 . . ?
 O4 C18 H18B 109.5 . . ?
 O4 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 C10 C19 H19 116.6 . . ?
 C20 C19 C10 126.7(5) . . ?
 C20 C19 H19 116.6 . . ?
 C19 C20 H20 116.3 . . ?
 C19 C20 C21 127.4(6) . . ?
 C21 C20 H20 116.3 . . ?
 C22 C21 C20 119.8(6) . . ?
 C22 C21 C26 118.2(5) . . ?
 C26 C21 C20 121.9(5) . . ?
 C21 C22 H22 118.7 . . ?
 C23 C22 C21 122.7(6) . . ?
 C23 C22 H22 118.7 . . ?
 C22 C23 H23 121.1 . . ?
 C24 C23 C22 117.8(7) . . ?
 C24 C23 H23 121.1 . . ?
 C23 C24 H24 119.5 . . ?
 C25 C24 C23 121.0(6) . . ?
 C25 C24 H24 119.5 . . ?
 C24 C25 H25 119.2 . . ?
 C24 C25 C26 121.7(6) . . ?
 C26 C25 H25 119.2 . . ?
 C21 C26 C25 118.6(6) . . ?
 C21 C26 C27 122.9(5) . . ?
 C25 C26 C27 118.5(6) . . ?
 C26 C27 H27A 109.5 . . ?
 C26 C27 H27B 109.5 . . ?
 C26 C27 H27C 109.5 . . ?
 H27A C27 H27B 109.5 . . ?
 H27A C27 H27C 109.5 . . ?
 H27B C27 H27C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
