# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_c29
_database_code_depnum_ccdc_archive 'CCDC 1888277'
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H28 O2'
_chemical_formula_sum            'C29 H28 O2'
_chemical_formula_weight         408.51
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2239(5)
_cell_length_b                   11.0090(6)
_cell_length_c                   11.0538(6)
_cell_angle_alpha                73.729(5)
_cell_angle_beta                 86.050(5)
_cell_angle_gamma                65.798(5)
_cell_volume                     1087.85(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4498
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6670
_cell_measurement_theta_min      2.8240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11241
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.111
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.00    --   11.74 -57.00  90.00  100
  2  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00   0.00  109
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00-120.00  101
  4  ω     34.00  99.00   1.00    1.00    --   11.74-178.00  90.00   65
  5  ω    -16.00  23.00   1.00    1.00    --   11.74  57.00 120.00   39
  6  ω    -20.00  16.00   1.00    1.00    --   11.74 -99.00 -90.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0130985000
_diffrn_orient_matrix_UB_12      -0.0709422000
_diffrn_orient_matrix_UB_13      0.0252903000
_diffrn_orient_matrix_UB_21      0.0729299000
_diffrn_orient_matrix_UB_22      -0.0191298000
_diffrn_orient_matrix_UB_23      -0.0153906000
_diffrn_orient_matrix_UB_31      0.0176374000
_diffrn_orient_matrix_UB_32      0.0022868000
_diffrn_orient_matrix_UB_33      0.0600352000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3052
_reflns_number_total             3818
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.043
_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)+(0.0561P)²+0.1795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1198
_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 Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C12(H12), C11(H11), C9(H9), C16(H16), C10(H10), C18(H18),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.36263(12) 0.19055(11) 0.85450(10) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.55052(14) 0.25367(14) 1.14998(11) 0.0381(4) Uani 1 1 d . . . . .
C20 C 0.53102(17) 0.21703(16) 0.95406(14) 0.0215(4) Uani 1 1 d . . . . .
C14 C 0.75946(17) 0.32138(16) 0.80149(14) 0.0207(4) Uani 1 1 d . . . . .
C4 C 0.63890(17) 0.30836(16) 0.61381(14) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.55751(17) 0.24446(16) 0.81997(14) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.45021(17) 0.22783(16) 0.76411(14) 0.0213(4) Uani 1 1 d . . . . .
C13 C 0.71868(17) 0.35605(16) 0.50721(14) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.52913(17) 0.28700(16) 0.56258(14) 0.0211(4) Uani 1 1 d . . . . .
C3 C 0.65483(17) 0.28915(16) 0.74392(14) 0.0205(4) Uani 1 1 d . . . . .
C21 C 0.41402(17) 0.18685(17) 0.96829(14) 0.0226(4) Uani 1 1 d . . . . .
C29 C 0.61398(18) 0.20465(17) 1.06584(15) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.53451(19) 0.31889(19) 0.42113(15) 0.0241(4) Uani 1 1 d . . . . .
C15 C 0.90705(18) 0.24427(18) 0.80351(14) 0.0266(4) Uani 1 1 d . . . . .
H15 H 0.942038 0.172194 0.765693 0.032 Uiso 1 1 calc R . . . .
C6 C 0.42858(17) 0.24817(16) 0.63542(14) 0.0222(4) Uani 1 1 d . . . . .
C19 C 0.70998(19) 0.42882(17) 0.85856(14) 0.0263(4) Uani 1 1 d . . . . .
H19 H 0.611843 0.481844 0.857322 0.032 Uiso 1 1 calc R . . . .
C8 C 0.65886(17) 0.35998(16) 0.39479(14) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.83379(18) 0.39397(17) 0.50200(15) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.873846 0.392670 0.575634 0.030 Uiso 1 1 calc R . . . .
C24 C 0.30859(18) 0.23047(17) 0.58204(15) 0.0252(4) Uani 1 1 d . . . . .
H24A H 0.298779 0.272173 0.491508 0.030 Uiso 1 1 calc R . . . .
H24B H 0.219675 0.280075 0.617385 0.030 Uiso 1 1 calc R . . . .
C11 C 0.88833(19) 0.43372(17) 0.38614(15) 0.0285(4) Uani 1 1 d . . . . .
H11 H 0.965149 0.459036 0.382451 0.034 Uiso 1 1 calc R . . . .
C9 C 0.71390(19) 0.39991(18) 0.27965(15) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.673763 0.402470 0.205497 0.034 Uiso 1 1 calc R . . . .
C22 C 0.33728(19) 0.14415(18) 1.08047(15) 0.0283(4) Uani 1 1 d . . . . .
H22A H 0.243768 0.216869 1.078695 0.043 Uiso 1 1 calc GR . . . .
H22B H 0.390967 0.126636 1.155998 0.043 Uiso 1 1 calc GR . . . .
H22C H 0.327624 0.061411 1.079063 0.043 Uiso 1 1 calc GR . . . .
C25 C 0.33016(18) 0.07954(18) 0.60803(15) 0.0269(4) Uani 1 1 d . . . . .
H25A H 0.335876 0.038906 0.698568 0.032 Uiso 1 1 calc R . . . .
H25B H 0.421001 0.029010 0.575794 0.032 Uiso 1 1 calc R . . . .
C16 C 1.00214(19) 0.2737(2) 0.86110(16) 0.0323(4) Uani 1 1 d . . . . .
H16 H 1.100474 0.222146 0.861077 0.039 Uiso 1 1 calc R . . . .
C10 C 0.82918(19) 0.43594(18) 0.27603(16) 0.0308(4) Uani 1 1 d . . . . .
H10 H 0.867222 0.461839 0.199116 0.037 Uiso 1 1 calc R . . . .
C26 C 0.21074(18) 0.06163(18) 0.54890(15) 0.0277(4) Uani 1 1 d . . . . .
H26A H 0.219851 -0.032754 0.584972 0.033 Uiso 1 1 calc R . . . .
H26B H 0.118892 0.122850 0.571420 0.033 Uiso 1 1 calc R . . . .
C23 C 0.77330(19) 0.12162(19) 1.07916(16) 0.0337(5) Uani 1 1 d . . . . .
H23A H 0.821073 0.182484 1.070079 0.051 Uiso 1 1 calc GR . . . .
H23B H 0.802206 0.073630 1.015044 0.051 Uiso 1 1 calc GR . . . .
H23C H 0.798640 0.055559 1.160876 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.8044(2) 0.45792(19) 0.91702(16) 0.0334(5) Uani 1 1 d . . . . .
H18 H 0.769815 0.529763 0.955120 0.040 Uiso 1 1 calc R . . . .
C17 C 0.9508(2) 0.3798(2) 0.91874(16) 0.0360(5) Uani 1 1 d . . . . .
H17 H 1.014575 0.398693 0.958639 0.043 Uiso 1 1 calc R . . . .
C27 C 0.21062(19) 0.0914(2) 0.40610(16) 0.0322(4) Uani 1 1 d . . . . .
H27A H 0.303845 0.033444 0.382851 0.039 Uiso 1 1 calc R . . . .
H27B H 0.195999 0.187271 0.369332 0.039 Uiso 1 1 calc R . . . .
C28 C 0.0953(2) 0.0654(2) 0.35118(17) 0.0384(5) Uani 1 1 d . . . . .
H28A H 0.101886 0.083424 0.261338 0.058 Uiso 1 1 calc GR . . . .
H28B H 0.002323 0.125759 0.370187 0.058 Uiso 1 1 calc GR . . . .
H28C H 0.108811 -0.029266 0.387352 0.058 Uiso 1 1 calc GR . . . .
H7A H 0.442(2) 0.3931(19) 0.3798(16) 0.035(5) Uiso 1 1 d . . . . .
H7B H 0.5476(18) 0.2383(19) 0.3888(15) 0.029(5) Uiso 1 1 d . . . . .


_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 1.3846(19) . ?
O1 C21 1.3801(18) . ?
O2 C29 1.220(2) . ?
C20 C2 1.457(2) . ?
C20 C21 1.355(2) . ?
C20 C29 1.490(2) . ?
C14 C3 1.485(2) . ?
C14 C15 1.393(2) . ?
C14 C19 1.392(2) . ?
C4 C13 1.484(2) . ?
C4 C5 1.419(2) . ?
C4 C3 1.405(2) . ?
C2 C1 1.393(2) . ?
C2 C3 1.412(2) . ?
C1 C6 1.395(2) . ?
C13 C8 1.405(2) . ?
C13 C12 1.394(2) . ?
C5 C7 1.506(2) . ?
C5 C6 1.393(2) . ?
C21 C22 1.489(2) . ?
C29 C23 1.499(2) . ?
C7 C8 1.501(2) . ?
C15 C16 1.383(2) . ?
C6 C24 1.500(2) . ?
C19 C18 1.381(2) . ?
C8 C9 1.386(2) . ?
C12 C11 1.389(2) . ?
C24 C25 1.527(2) . ?
C11 C10 1.386(2) . ?
C9 C10 1.384(2) . ?
C25 C26 1.529(2) . ?
C16 C17 1.384(3) . ?
C26 C27 1.520(2) . ?
C18 C17 1.385(3) . ?
C27 C28 1.521(2) . ?

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
C21 O1 C1 106.17(12) . . ?
C2 C20 C29 132.11(15) . . ?
C21 C20 C2 106.66(13) . . ?
C21 C20 C29 120.91(14) . . ?
C15 C14 C3 121.87(15) . . ?
C19 C14 C3 119.66(15) . . ?
C19 C14 C15 118.44(15) . . ?
C5 C4 C13 107.64(13) . . ?
C3 C4 C13 130.71(15) . . ?
C3 C4 C5 121.60(14) . . ?
C1 C2 C20 105.17(13) . . ?
C1 C2 C3 119.87(14) . . ?
C3 C2 C20 134.79(15) . . ?
O1 C1 C2 110.48(13) . . ?
O1 C1 C6 123.33(14) . . ?
C6 C1 C2 126.18(14) . . ?
C8 C13 C4 108.28(14) . . ?
C12 C13 C4 132.41(14) . . ?
C12 C13 C8 119.31(15) . . ?
C4 C5 C7 110.27(14) . . ?
C6 C5 C4 123.34(14) . . ?
C6 C5 C7 126.33(14) . . ?
C4 C3 C14 123.90(14) . . ?
C4 C3 C2 115.93(14) . . ?
C2 C3 C14 120.06(13) . . ?
O1 C21 C22 115.22(14) . . ?
C20 C21 O1 111.51(14) . . ?
C20 C21 C22 133.17(15) . . ?
O2 C29 C20 119.67(15) . . ?
O2 C29 C23 120.49(15) . . ?
C20 C29 C23 119.63(15) . . ?
C8 C7 C5 103.11(13) . . ?
C16 C15 C14 120.78(17) . . ?
C1 C6 C24 123.06(14) . . ?
C5 C6 C1 113.01(14) . . ?
C5 C6 C24 123.93(14) . . ?
C18 C19 C14 121.00(16) . . ?
C13 C8 C7 110.68(14) . . ?
C9 C8 C13 120.68(16) . . ?
C9 C8 C7 128.63(15) . . ?
C11 C12 C13 119.59(15) . . ?
C6 C24 C25 113.88(13) . . ?
C10 C11 C12 120.53(16) . . ?
C8 C9 C10 119.38(16) . . ?
C24 C25 C26 113.71(14) . . ?
C17 C16 C15 119.94(17) . . ?
C9 C10 C11 120.50(16) . . ?
C27 C26 C25 114.55(14) . . ?
C19 C18 C17 119.84(17) . . ?
C16 C17 C18 119.99(17) . . ?
C26 C27 C28 113.11(15) . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.065
_oxdiff_exptl_absorpt_empirical_full_min 0.537
####################################################################### 
# 
# 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_65-1-2
_database_code_depnum_ccdc_archive 'CCDC 1888278'
_audit_update_record             
;
2019-01-02 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;
_audit_creation_date             2018-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 O3'
_chemical_formula_sum            'C26 H20 O3'
_chemical_formula_weight         380.42
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5269(6)
_cell_length_b                   6.9766(4)
_cell_length_c                   23.8120(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.369(5)
_cell_angle_gamma                90
_cell_volume                     1894.54(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4904
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.2450
_cell_measurement_theta_min      2.9250
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11699
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  38.00   1.00    2.00    --   11.74 -57.00 -60.00   96
  2  ω    -15.00  78.00   1.00    2.00    --   11.74  77.00-150.00   93
  3  ω    -11.00  81.00   1.00    2.00    --   11.74  57.00  90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0582420000
_diffrn_orient_matrix_UB_12      0.0311662000
_diffrn_orient_matrix_UB_13      0.0091631000
_diffrn_orient_matrix_UB_21      0.0193085000
_diffrn_orient_matrix_UB_22      -0.0966202000
_diffrn_orient_matrix_UB_23      0.0014071000
_diffrn_orient_matrix_UB_31      0.0100413000
_diffrn_orient_matrix_UB_32      0.0051287000
_diffrn_orient_matrix_UB_33      -0.0286626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2901
_reflns_number_total             3333
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0074(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.084
_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)+(0.0417P)²+0.6223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C23(H23), C3(H3), C6(H6), C5(H5), C22(H22), C4(H4), C15(H15),
 C19(H19), C17(H17), C18(H18), C16(H16)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.49939(9) 0.23511(15) 0.56613(4) 0.0213(3) Uani 1 1 d . . . . .
O3 O 0.98244(9) 0.18825(15) 0.45026(5) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.99282(10) 0.48838(18) 0.41903(5) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.64156(12) 0.3302(2) 0.33026(6) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.56270(12) 0.3006(2) 0.36763(6) 0.0166(3) Uani 1 1 d . . . . .
C20 C 0.52712(13) 0.2619(2) 0.46729(6) 0.0169(3) Uani 1 1 d . . . . .
H20 H 0.447080 0.251141 0.454854 0.020 Uiso 1 1 calc R . . . .
C10 C 0.80705(13) 0.3305(2) 0.40648(6) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.72843(12) 0.3006(2) 0.44665(6) 0.0160(3) Uani 1 1 d . . . . .
C12 C 0.60541(12) 0.2862(2) 0.42705(6) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.62479(13) 0.3444(2) 0.26763(6) 0.0169(3) Uani 1 1 d . . . . .
C23 C 0.76660(13) 0.2916(2) 0.50612(6) 0.0181(3) Uani 1 1 d . . . . .
H23 H 0.846212 0.301880 0.519637 0.022 Uiso 1 1 calc R . . . .
C9 C 0.76435(12) 0.3452(2) 0.34979(6) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.83098(13) 0.3660(2) 0.30017(6) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.43407(13) 0.2805(2) 0.34780(6) 0.0176(3) Uani 1 1 d . . . . .
C21 C 0.56792(13) 0.2540(2) 0.52421(6) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.73503(13) 0.3631(2) 0.25004(6) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.52372(13) 0.3395(2) 0.22730(6) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.450113 0.327518 0.238557 0.023 Uiso 1 1 calc R . . . .
C6 C 0.74509(13) 0.3746(2) 0.19279(6) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.818442 0.385831 0.181212 0.023 Uiso 1 1 calc R . . . .
C25 C 0.93621(13) 0.3481(2) 0.42531(6) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.64450(13) 0.3691(2) 0.15301(6) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.650530 0.376361 0.114549 0.025 Uiso 1 1 calc R . . . .
C22 C 0.68942(13) 0.2684(2) 0.54372(6) 0.0198(3) Uani 1 1 d . . . . .
H22 H 0.716708 0.262077 0.582404 0.024 Uiso 1 1 calc R . . . .
C4 C 0.53510(13) 0.3528(2) 0.17014(6) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.468360 0.350678 0.142999 0.024 Uiso 1 1 calc R . . . .
C24 C 0.37589(12) 0.2256(2) 0.54865(6) 0.0211(4) Uani 1 1 d . . . . .
H24A H 0.350927 0.334985 0.525571 0.032 Uiso 1 1 calc GR . . . .
H24B H 0.336473 0.224725 0.581498 0.032 Uiso 1 1 calc GR . . . .
H24C H 0.357079 0.110538 0.527114 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.38387(14) 0.1000(2) 0.33939(7) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.430568 -0.008657 0.346114 0.033 Uiso 1 1 calc R . . . .
C19 C 0.36236(14) 0.4400(2) 0.33811(7) 0.0271(4) Uani 1 1 d . . . . .
H19 H 0.394521 0.561945 0.343686 0.033 Uiso 1 1 calc R . . . .
C26 C 1.10669(13) 0.1964(2) 0.47074(7) 0.0278(4) Uani 1 1 d . . . . .
H26A H 1.148565 0.225222 0.439754 0.042 Uiso 1 1 calc GR . . . .
H26B H 1.132384 0.074957 0.486945 0.042 Uiso 1 1 calc GR . . . .
H26C H 1.121640 0.294572 0.499136 0.042 Uiso 1 1 calc GR . . . .
C17 C 0.19436(14) 0.2396(3) 0.31154(7) 0.0325(4) Uani 1 1 d . . . . .
H17 H 0.114416 0.225890 0.299338 0.039 Uiso 1 1 calc R . . . .
C18 C 0.24279(14) 0.4194(3) 0.32014(7) 0.0345(4) Uani 1 1 d . . . . .
H18 H 0.195391 0.527423 0.313919 0.041 Uiso 1 1 calc R . . . .
C16 C 0.26481(14) 0.0804(3) 0.32107(7) 0.0338(4) Uani 1 1 d . . . . .
H16 H 0.232284 -0.041241 0.315179 0.041 Uiso 1 1 calc R . . . .
H8A H 0.8786(13) 0.484(2) 0.3024(6) 0.020(4) Uiso 1 1 d . . . . .
H8B H 0.8878(14) 0.262(2) 0.2993(7) 0.023(4) Uiso 1 1 d . . . . .


_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 C21 1.3664(18) . ?
O1 C24 1.4255(17) . ?
O3 C25 1.3371(18) . ?
O3 C26 1.4453(17) . ?
O2 C25 1.1979(18) . ?
C1 C13 1.377(2) . ?
C1 C2 1.479(2) . ?
C1 C9 1.4280(19) . ?
C13 C12 1.432(2) . ?
C13 C14 1.496(2) . ?
C20 H20 0.9300 . ?
C20 C12 1.419(2) . ?
C20 C21 1.370(2) . ?
C10 C11 1.425(2) . ?
C10 C9 1.372(2) . ?
C10 C25 1.496(2) . ?
C11 C12 1.430(2) . ?
C11 C23 1.422(2) . ?
C2 C7 1.401(2) . ?
C2 C3 1.398(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.361(2) . ?
C9 C8 1.507(2) . ?
C8 C7 1.505(2) . ?
C8 H8A 0.989(17) . ?
C8 H8B 0.979(17) . ?
C14 C15 1.388(2) . ?
C14 C19 1.385(2) . ?
C21 C22 1.414(2) . ?
C7 C6 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(2) . ?
C22 H22 0.9300 . ?
C4 H4 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.390(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C17 C16 1.375(3) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?

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
C21 O1 C24 116.76(11) . . ?
C25 O3 C26 115.36(12) . . ?
C13 C1 C2 131.30(13) . . ?
C13 C1 C9 121.13(13) . . ?
C9 C1 C2 107.53(12) . . ?
C1 C13 C12 118.98(13) . . ?
C1 C13 C14 121.82(12) . . ?
C12 C13 C14 119.19(13) . . ?
C12 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C12 120.83(13) . . ?
C11 C10 C25 120.86(12) . . ?
C9 C10 C11 119.95(13) . . ?
C9 C10 C25 119.19(13) . . ?
C10 C11 C12 119.22(13) . . ?
C23 C11 C10 122.69(13) . . ?
C23 C11 C12 118.05(13) . . ?
C20 C12 C13 120.96(13) . . ?
C20 C12 C11 119.07(13) . . ?
C11 C12 C13 119.95(13) . . ?
C7 C2 C1 108.46(12) . . ?
C3 C2 C1 131.63(14) . . ?
C3 C2 C7 119.91(14) . . ?
C11 C23 H23 119.2 . . ?
C22 C23 C11 121.57(13) . . ?
C22 C23 H23 119.2 . . ?
C1 C9 C8 110.24(12) . . ?
C10 C9 C1 120.77(13) . . ?
C10 C9 C8 128.90(13) . . ?
C9 C8 H8A 112.4(9) . . ?
C9 C8 H8B 111.4(9) . . ?
C7 C8 C9 102.77(12) . . ?
C7 C8 H8A 113.1(9) . . ?
C7 C8 H8B 112.9(9) . . ?
H8A C8 H8B 104.5(13) . . ?
C15 C14 C13 120.24(14) . . ?
C19 C14 C13 121.17(14) . . ?
C19 C14 C15 118.58(14) . . ?
O1 C21 C20 125.10(13) . . ?
O1 C21 C22 114.66(12) . . ?
C20 C21 C22 120.23(14) . . ?
C2 C7 C8 110.99(13) . . ?
C6 C7 C2 120.55(13) . . ?
C6 C7 C8 128.45(14) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.89(14) . . ?
C4 C3 H3 120.6 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.23(14) . . ?
C5 C6 H6 120.4 . . ?
O3 C25 C10 112.31(13) . . ?
O2 C25 O3 123.22(13) . . ?
O2 C25 C10 124.47(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(14) . . ?
C4 C5 H5 119.7 . . ?
C23 C22 C21 120.24(13) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.90(14) . . ?
C5 C4 H4 119.5 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.54(16) . . ?
C16 C15 H15 119.7 . . ?
C14 C19 H19 119.7 . . ?
C14 C19 C18 120.62(16) . . ?
C18 C19 H19 119.7 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.65(15) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.17(16) . . ?
C17 C18 H18 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.42(16) . . ?
C17 C16 H16 119.8 . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.692
