# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_017rck17
_database_code_depnum_ccdc_archive 'CCDC 1852221'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 O4'
_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_weight         294.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H14O4
_chemical_oxdiff_usercomment     
'017RCK17 colourless block 0.4 0.4 0.12 EtOAc/hexane Cu150K 4x4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.80656(8)
_cell_length_b                   17.94783(10)
_cell_length_c                   7.75427(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.5855(8)
_cell_angle_gamma                90
_cell_volume                     1407.942(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19058
_cell_measurement_temperature    150.04(10)
_cell_measurement_theta_max      73.2670
_cell_measurement_theta_min      4.3480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27954
_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    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.502
_diffrn_reflns_theta_min         4.370
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -42.36 125.00  30.00   94
  2  ω   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00  90.00   95
  3  ω   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00 -90.00   95
  4  ω   -115.00 -20.00   1.00    1.00    --  -42.36 -37.00-180.00   95
  5  ω     23.00  97.00   1.00    1.00    --   42.36-125.00  90.00   74
  6  ω     23.00  97.00   1.00    1.00    --   42.36-125.00-180.00   74
  7  ω     94.00 178.00   1.00    1.00    --  106.00 125.00   0.00   84
  8  ω     31.00 130.00   1.00    1.00    --  106.00 -30.00  90.00   99
  9  ω     32.00 137.00   1.00    1.00    --  106.00 -77.00   0.00  105
 10  ω     34.00 121.00   1.00    1.00    --  106.00-125.00 120.00   87
 11  ω     94.00 178.00   1.00    1.00    --  106.00 125.00  90.00   84
 12  ω     34.00 121.00   1.00    1.00    --  106.00-125.00 -90.00   87
 13  ω     82.00 178.00   1.00    1.00    --  106.00  30.00 -30.00   96
 14  ω     25.00 109.00   1.00    1.00    --  106.00 -94.00 120.00   84
 15  ω     82.00 177.00   1.00    1.00    --  106.00  45.00  60.00   95
 16  ω     25.00 109.00   1.00    1.00    --  106.00 -94.00 -30.00   84
 17  ω     94.00 178.00   1.00    1.00    --  106.00 125.00 -30.00   84
 18  ω     34.00 121.00   1.00    1.00    --  106.00-125.00 -30.00   87
 19  ω     36.00 134.00   1.00    1.00    --  106.00 -61.00 -60.00   98
 20  ω     36.00 134.00   1.00    1.00    --  106.00 -61.00  90.00   98
 21  ω     82.00 178.00   1.00    1.00    --  106.00  30.00   0.00   96
 22  ω     34.00 121.00   1.00    1.00    --  106.00-125.00   0.00   87
 23  ω     94.00 178.00   1.00    1.00    --  106.00 125.00 120.00   84
 24  ω     35.00 130.00   1.00    1.00    --  106.00 -45.00-150.00   95
 25  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00-180.00  105
 26  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00  90.00  105
 27  ω   -113.00 -16.00   1.00    1.00    --  -42.36 -57.00  30.00   97
 28  ω   -116.00 -11.00   1.00    1.00    --  -42.36 -77.00 -90.00  105
 29  ω     11.00 116.00   1.00    1.00    --   42.36  77.00   0.00  105
 30  ω      1.00  82.00   1.00    1.00    --   42.36 -99.00 -90.00   81
 31  ω     82.00 178.00   1.00    1.00    --  106.00  30.00-120.00   96
 32  ω     78.00 176.00   1.00    1.00    --  106.00  61.00-180.00   98
 33  ω     78.00 176.00   1.00    1.00    --  106.00  61.00 -90.00   98
 34  ω     61.00 178.00   1.00    1.00    --  106.00  15.00-180.00  117
;
_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      -0.1277972000
_diffrn_orient_matrix_UB_12      -0.0458996000
_diffrn_orient_matrix_UB_13      -0.0429071000
_diffrn_orient_matrix_UB_21      -0.0826198000
_diffrn_orient_matrix_UB_22      0.0716983000
_diffrn_orient_matrix_UB_23      -0.0582116000
_diffrn_orient_matrix_UB_31      -0.0053316000
_diffrn_orient_matrix_UB_32      -0.0110458000
_diffrn_orient_matrix_UB_33      -0.1995004000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2738
_reflns_number_total             2829
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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         0.265
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+0.4940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1217
_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:
 C14(H14A,H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C2(H2), C5(H5), C4(H4), C3(H3), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
O18 O 0.72132(9) 0.69493(5) 0.49569(12) 0.0220(2) Uani 1 1 d . . . . .
O13 O 0.62189(8) 0.46911(5) 0.34487(11) 0.0197(2) Uani 1 1 d . . . . .
O21 O 0.83922(9) 0.39030(5) 0.37461(13) 0.0235(2) Uani 1 1 d . . . . .
O20 O 1.01227(10) 0.66104(5) 0.06120(14) 0.0298(3) Uani 1 1 d . . . . .
C12 C 0.72098(11) 0.50223(7) 0.29918(15) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.70586(12) 0.57655(6) 0.23853(15) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.58823(12) 0.62092(6) 0.23609(16) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.80154(12) 0.60806(7) 0.17946(16) 0.0177(3) Uani 1 1 d . . . . .
H8 H 0.791852 0.656864 0.136442 0.021 Uiso 1 1 calc R . . . .
C11 C 0.83380(12) 0.46100(7) 0.30795(16) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.91189(12) 0.56676(7) 0.18452(16) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.59920(12) 0.67849(7) 0.36243(16) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.92914(12) 0.49329(7) 0.25072(16) 0.0187(3) Uani 1 1 d . . . . .
H10 H 1.004068 0.466500 0.256089 0.022 Uiso 1 1 calc R . . . .
C2 C 0.49017(13) 0.72131(7) 0.35406(18) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.499339 0.759754 0.438084 0.028 Uiso 1 1 calc R . . . .
C5 C 0.46381(12) 0.60707(7) 0.10392(17) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.454092 0.568756 0.019401 0.024 Uiso 1 1 calc R . . . .
C15 C 0.69239(13) 0.52583(7) 0.63793(17) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.65445(13) 0.45487(7) 0.54000(17) 0.0221(3) Uani 1 1 d . . . . .
H14A H 0.726908 0.419620 0.582985 0.027 Uiso 1 1 calc R . . . .
H14B H 0.578688 0.433949 0.562312 0.027 Uiso 1 1 calc R . . . .
C4 C 0.35440(13) 0.64930(7) 0.09615(17) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.272248 0.639050 0.007574 0.027 Uiso 1 1 calc R . . . .
C3 C 0.36796(13) 0.70700(7) 0.22119(18) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.295157 0.735860 0.215536 0.029 Uiso 1 1 calc R . . . .
C19 C 1.01432(13) 0.59863(7) 0.12212(17) 0.0218(3) Uani 1 1 d . . . . .
H19 H 1.086238 0.568602 0.129995 0.026 Uiso 1 1 calc R . . . .
C16 C 0.71862(13) 0.58973(8) 0.67887(17) 0.0239(3) Uani 1 1 d . . . . .
C22 C 0.95029(14) 0.34554(7) 0.37995(19) 0.0252(3) Uani 1 1 d . . . . .
H22A H 0.947678 0.336660 0.256636 0.038 Uiso 1 1 calc GR . . . .
H22B H 0.946994 0.298829 0.438522 0.038 Uiso 1 1 calc GR . . . .
H22C H 1.030607 0.371122 0.448282 0.038 Uiso 1 1 calc GR . . . .
C17 C 0.73227(14) 0.67101(8) 0.67868(17) 0.0255(3) Uani 1 1 d . . . . .
H17A H 0.663626 0.694265 0.713811 0.031 Uiso 1 1 calc R . . . .
H17B H 0.817391 0.685708 0.766842 0.031 Uiso 1 1 calc R . . . .


_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
O18 C1 1.3919(15) . ?
O18 C17 1.4469(16) . ?
O13 C12 1.3756(14) . ?
O13 C14 1.4506(15) . ?
O21 C11 1.3635(15) . ?
O21 C22 1.4328(15) . ?
O20 C19 1.2127(17) . ?
C12 C7 1.4047(16) . ?
C12 C11 1.4072(17) . ?
C7 C6 1.4945(16) . ?
C7 C8 1.3899(17) . ?
C6 C1 1.3999(17) . ?
C6 C5 1.3968(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3929(17) . ?
C11 C10 1.3842(18) . ?
C9 C10 1.4035(17) . ?
C9 C19 1.4708(17) . ?
C1 C2 1.3891(18) . ?
C10 H10 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.3838(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.3879(18) . ?
C15 C14 1.4655(18) . ?
C15 C16 1.197(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.3907(19) . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?
C16 C17 1.4663(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C1 O18 C17 113.23(10) . . ?
C12 O13 C14 114.80(9) . . ?
C11 O21 C22 117.17(10) . . ?
O13 C12 C7 119.15(10) . . ?
O13 C12 C11 120.00(10) . . ?
C7 C12 C11 120.82(11) . . ?
C12 C7 C6 120.57(11) . . ?
C8 C7 C12 118.97(11) . . ?
C8 C7 C6 120.46(10) . . ?
C1 C6 C7 121.47(11) . . ?
C5 C6 C7 120.63(11) . . ?
C5 C6 C1 117.89(11) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.20(11) . . ?
C9 C8 H8 119.9 . . ?
O21 C11 C12 115.38(11) . . ?
O21 C11 C10 125.00(11) . . ?
C10 C11 C12 119.62(11) . . ?
C8 C9 C10 120.83(11) . . ?
C8 C9 C19 121.31(11) . . ?
C10 C9 C19 117.85(11) . . ?
O18 C1 C6 120.06(11) . . ?
C2 C1 O18 118.98(11) . . ?
C2 C1 C6 120.93(11) . . ?
C11 C10 C9 119.51(11) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(12) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.35(11) . . ?
C4 C5 H5 119.3 . . ?
C16 C15 C14 165.23(13) . . ?
O13 C14 C15 107.96(10) . . ?
O13 C14 H14A 110.1 . . ?
O13 C14 H14B 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.81(11) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 119.76(12) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O20 C19 C9 125.07(12) . . ?
O20 C19 H19 117.5 . . ?
C9 C19 H19 117.5 . . ?
C15 C16 C17 165.32(13) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O18 C17 C16 108.82(10) . . ?
O18 C17 H17A 109.9 . . ?
O18 C17 H17B 109.9 . . ?
C16 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?

_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 4.768
_oxdiff_exptl_absorpt_empirical_full_min 0.484
####################################################################### 
# 
# 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_026rck18
_database_code_depnum_ccdc_archive 'CCDC 1852224'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 B F2 N2 O3'
_chemical_formula_sum            'C26 H19 B F2 N2 O3'
_chemical_formula_weight         456.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H19BF2N2O3
_chemical_oxdiff_usercomment     
'026RCK18 red block 0.25 0.10 0.07 chcl3 Cu150K 4x4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.4282(2)
_cell_length_b                   25.2193(4)
_cell_length_c                   7.59768(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.5629(17)
_cell_angle_gamma                90
_cell_volume                     2119.39(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8515
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.0940
_cell_measurement_theta_min      4.3620
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13289
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.493
_diffrn_reflns_theta_min         3.505
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -18.00   1.00    8.22    --  -42.09 -38.00  90.00   98
  2  ω    -67.00  32.00   1.00    8.22    --  -42.09  38.00  90.00   99
  3  ω     18.00  98.00   1.00    8.22    --   42.09-125.00-180.00   80
  4  ω     86.00 178.00   1.00   32.90    --  114.00  30.00   0.00   92
  5  ω     38.00 116.00   1.00   32.90    --  114.00-111.00 120.00   78
  6  ω     32.00 109.00   1.00   32.90    --  114.00 -95.00 150.00   77
  7  ω     88.00 178.00   1.00   32.90    --  114.00  45.00-120.00   90
  8  ω     86.00 178.00   1.00   32.90    --  114.00  30.00 -90.00   92
  9  ω     32.00 109.00   1.00   32.90    --  114.00 -95.00-180.00   77
 10  ω    100.00 178.00   1.00   32.90    --  114.00 111.00-120.00   78
 11  ω     41.00 140.00   1.00   32.90    --  114.00 -45.00 -60.00   99
 12  ω   -118.00 -56.00   1.00    8.22    --  -42.09 -77.00 -30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0824372000
_diffrn_orient_matrix_UB_12      -0.0008890000
_diffrn_orient_matrix_UB_13      -0.1323021000
_diffrn_orient_matrix_UB_21      -0.1101447000
_diffrn_orient_matrix_UB_22      0.0110579000
_diffrn_orient_matrix_UB_23      -0.1602445000
_diffrn_orient_matrix_UB_31      0.0214593000
_diffrn_orient_matrix_UB_32      0.0600457000
_diffrn_orient_matrix_UB_33      0.0276162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4198
_reflns_number_total             4488
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4488
_refine_ls_number_restraints     141
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.6242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1148
_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. Restrained distances
 N26-N30 \\sim N26-F28 \\sim N26-F29 \\sim N30-F28 \\sim N30-F29 \\sim F28-F29
 with sigma of 0.04
 B27-N26 \\sim B27-N30 \\sim B27-F28 \\sim B27-F29
 with sigma of 0.02
 N26-N30 \\sim F129-F128
 with sigma of 0.04
 B127-N26 \\sim B127-N30 \\sim B127-F129 \\sim B127-F128
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
B27 \\sim F29 \\sim F28: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F129 \\sim F128 \\sim B127 \\sim N30 \\sim N26: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
F28 \\sim B27 \\sim F128 \\sim B127 \\sim F29 \\sim F129: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
B127 \\sim N26 \\sim N30: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
B127 \\sim N30 \\sim N26 \\sim C22 \\sim C34 \\sim B27: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(F129)=Sof(B127)=Sof(F128)=1-FVAR(1)
 Sof(F28)=Sof(F29)=Sof(B27)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C5(H5), C4(H4), C23(H23), C2(H2), C33(H33), C3(H3),
 C25(H25), C32(H32), C24(H24), C31(H31)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
O18 O 0.18166(8) 0.69699(3) 0.61743(13) 0.0310(2) Uani 1 1 d . . . . .
O19 O 0.44727(9) 0.54824(4) 0.27104(13) 0.0343(2) Uani 1 1 d . . . . .
O13 O 0.21800(9) 0.55871(4) 0.28947(13) 0.0316(2) Uani 1 1 d . . . . .
N26 N 0.79055(10) 0.63131(5) 1.08181(16) 0.0330(3) Uani 1 1 d D U . . .
N30 N 0.66611(11) 0.71250(5) 1.04694(17) 0.0379(3) Uani 1 1 d D U . . .
C12 C 0.37713(11) 0.61213(5) 0.73543(17) 0.0276(3) Uani 1 1 d . . . . .
H12 H 0.359702 0.625634 0.839876 0.033 Uiso 1 1 calc R . . . .
C10 C 0.52387(11) 0.58679(5) 0.57179(17) 0.0280(3) Uani 1 1 d . . . . .
H10 H 0.603859 0.583566 0.565882 0.034 Uiso 1 1 calc R . . . .
C7 C 0.28228(11) 0.59505(5) 0.59180(17) 0.0266(2) Uani 1 1 d . . . . .
C9 C 0.43073(12) 0.56928(5) 0.42849(17) 0.0279(3) Uani 1 1 d . . . . .
F28 F 0.7506(3) 0.67206(12) 1.3444(2) 0.0574(9) Uani 0.630(9) 1 d D U P A 1
C22 C 0.70023(11) 0.60705(5) 0.94841(17) 0.0289(3) Uani 1 1 d . U . . .
C11 C 0.49646(11) 0.60939(5) 0.72572(17) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.30963(11) 0.57401(5) 0.43730(17) 0.0277(3) Uani 1 1 d . . . . .
C6 C 0.15647(11) 0.60194(5) 0.60960(16) 0.0272(3) Uani 1 1 d . . . . .
C21 C 0.59232(12) 0.63422(5) 0.86965(17) 0.0285(3) Uani 1 1 d . . . . .
C5 C 0.08385(12) 0.55836(5) 0.62295(18) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.111894 0.524338 0.609923 0.037 Uiso 1 1 calc R . . . .
C4 C -0.02934(12) 0.56495(6) 0.65531(19) 0.0342(3) Uani 1 1 d . . . . .
H4 H -0.076240 0.535522 0.665437 0.041 Uiso 1 1 calc R . . . .
C1 C 0.11086(11) 0.65277(5) 0.62675(17) 0.0283(3) Uani 1 1 d . . . . .
C23 C 0.73653(12) 0.55452(5) 0.92700(19) 0.0319(3) Uani 1 1 d . . . . .
H23 H 0.693469 0.529230 0.847409 0.038 Uiso 1 1 calc R . . . .
C34 C 0.57472(12) 0.68618(5) 0.92106(18) 0.0324(3) Uani 1 1 d . U . . .
C2 C -0.00304(12) 0.65969(6) 0.65665(19) 0.0338(3) Uani 1 1 d . . . . .
H2 H -0.032693 0.693635 0.665983 0.041 Uiso 1 1 calc R . . . .
C15 C 0.17646(13) 0.64918(6) 0.20936(18) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.19765(13) 0.59676(6) 0.14027(18) 0.0365(3) Uani 1 1 d . . . . .
H14A H 0.128153 0.586101 0.044617 0.044 Uiso 1 1 calc R . . . .
H14B H 0.267648 0.597938 0.089933 0.044 Uiso 1 1 calc R . . . .
C17 C 0.14983(14) 0.72349(5) 0.44266(19) 0.0357(3) Uani 1 1 d . . . . .
H17A H 0.201272 0.754207 0.445026 0.043 Uiso 1 1 calc R . . . .
H17B H 0.066558 0.735452 0.416286 0.043 Uiso 1 1 calc R . . . .
F29 F 0.8765(2) 0.71451(9) 1.2012(5) 0.0650(11) Uani 0.630(9) 1 d D U P A 1
C16 C 0.16533(13) 0.68625(5) 0.30139(19) 0.0349(3) Uani 1 1 d . . . . .
C33 C 0.48141(13) 0.72369(6) 0.85193(19) 0.0358(3) Uani 1 1 d . . . . .
H33 H 0.409079 0.717135 0.766079 0.043 Uiso 1 1 calc R . . . .
C20 C 0.56848(14) 0.54349(6) 0.2550(2) 0.0382(3) Uani 1 1 d . . . . .
H20A H 0.568216 0.528404 0.138845 0.057 Uiso 1 1 calc GR . . . .
H20B H 0.613455 0.520944 0.349923 0.057 Uiso 1 1 calc GR . . . .
H20C H 0.605385 0.577927 0.265263 0.057 Uiso 1 1 calc GR . . . .
C3 C -0.07240(12) 0.61564(6) 0.6725(2) 0.0368(3) Uani 1 1 d . . . . .
H3 H -0.148164 0.620109 0.694832 0.044 Uiso 1 1 calc R . . . .
C25 C 0.87853(13) 0.59557(6) 1.1412(2) 0.0373(3) Uani 1 1 d . . . . .
H25 H 0.948981 0.601672 1.231536 0.045 Uiso 1 1 calc R . . . .
C32 C 0.51778(15) 0.77121(6) 0.9352(2) 0.0418(3) Uani 1 1 d . . . . .
H32 H 0.474829 0.802911 0.916995 0.050 Uiso 1 1 calc R . . . .
C24 C 0.84873(13) 0.54784(6) 1.0474(2) 0.0377(3) Uani 1 1 d . . . . .
H24 H 0.895563 0.517216 1.062923 0.045 Uiso 1 1 calc R . . . .
C31 C 0.63227(15) 0.76289(6) 1.0531(2) 0.0426(3) Uani 1 1 d . . . . .
H31 H 0.678183 0.788938 1.125604 0.051 Uiso 1 1 calc R . . . .
B27 B 0.7773(4) 0.68465(18) 1.1802(6) 0.0377(10) Uani 0.630(9) 1 d D U P A 1
F129 F 0.8823(4) 0.71783(15) 1.0626(18) 0.099(3) Uani 0.370(9) 1 d D U P A 2
B127 B 0.7917(9) 0.6900(4) 1.1229(14) 0.063(3) Uani 0.370(9) 1 d D U P A 2
F128 F 0.8147(8) 0.6979(3) 1.3126(9) 0.109(5) Uani 0.370(9) 1 d D U P A 2


_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
O18 C1 1.3901(15) . ?
O18 C17 1.4488(16) . ?
O19 C9 1.3645(15) . ?
O19 C20 1.4260(17) . ?
O13 C8 1.3840(15) . ?
O13 C14 1.4585(17) . ?
N26 C22 1.3932(17) . ?
N26 C25 1.3411(19) . ?
N26 B27 1.565(4) . ?
N26 B127 1.513(10) . ?
N30 C34 1.3942(17) . ?
N30 C31 1.333(2) . ?
N30 B27 1.577(5) . ?
N30 B127 1.515(10) . ?
C12 H12 0.9300 . ?
C12 C7 1.3986(17) . ?
C12 C11 1.3858(18) . ?
C10 H10 0.9300 . ?
C10 C9 1.3895(18) . ?
C10 C11 1.4054(18) . ?
C7 C8 1.3935(18) . ?
C7 C6 1.4878(17) . ?
C9 C8 1.4073(18) . ?
F28 B27 1.394(5) . ?
C22 C21 1.4062(18) . ?
C22 C23 1.4097(19) . ?
C11 C21 1.4784(17) . ?
C6 C5 1.3960(18) . ?
C6 C1 1.4022(18) . ?
C21 C34 1.3964(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.388(2) . ?
C1 C2 1.3875(19) . ?
C23 H23 0.9300 . ?
C23 C24 1.3855(19) . ?
C34 C33 1.4233(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C15 C14 1.465(2) . ?
C15 C16 1.193(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.470(2) . ?
F29 B27 1.336(5) . ?
C33 H33 0.9300 . ?
C33 C32 1.370(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.397(2) . ?
C32 H32 0.9300 . ?
C32 C31 1.403(2) . ?
C24 H24 0.9300 . ?
C31 H31 0.9300 . ?
F129 B127 1.419(10) . ?
B127 F128 1.413(9) . ?

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
C1 O18 C17 113.67(10) . . ?
C9 O19 C20 117.35(11) . . ?
C8 O13 C14 112.80(10) . . ?
C22 N26 B27 125.61(19) . . ?
C22 N26 B127 123.1(4) . . ?
C25 N26 C22 107.78(12) . . ?
C25 N26 B27 124.84(19) . . ?
C25 N26 B127 128.4(4) . . ?
C34 N30 B27 124.91(19) . . ?
C34 N30 B127 123.9(4) . . ?
C31 N30 C34 107.70(12) . . ?
C31 N30 B27 126.60(19) . . ?
C31 N30 B127 126.8(4) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C7 121.54(12) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.59(12) . . ?
C11 C10 H10 120.2 . . ?
C12 C7 C6 118.05(11) . . ?
C8 C7 C12 118.72(12) . . ?
C8 C7 C6 123.20(11) . . ?
O19 C9 C10 124.25(12) . . ?
O19 C9 C8 115.42(11) . . ?
C10 C9 C8 120.30(11) . . ?
N26 C22 C21 120.37(12) . . ?
N26 C22 C23 108.12(11) . . ?
C21 C22 C23 131.36(12) . . ?
C12 C11 C10 119.52(11) . . ?
C12 C11 C21 119.71(11) . . ?
C10 C11 C21 120.57(11) . . ?
O13 C8 C7 120.38(11) . . ?
O13 C8 C9 119.35(11) . . ?
C7 C8 C9 120.25(11) . . ?
C5 C6 C7 121.37(11) . . ?
C5 C6 C1 118.11(12) . . ?
C1 C6 C7 120.36(11) . . ?
C22 C21 C11 121.06(12) . . ?
C34 C21 C22 120.72(12) . . ?
C34 C21 C11 118.18(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.12(12) . . ?
C4 C5 H5 119.4 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.74(12) . . ?
C3 C4 H4 120.1 . . ?
O18 C1 C6 119.61(11) . . ?
C2 C1 O18 119.30(11) . . ?
C2 C1 C6 121.08(12) . . ?
C22 C23 H23 126.6 . . ?
C24 C23 C22 106.76(12) . . ?
C24 C23 H23 126.6 . . ?
N30 C34 C21 120.19(12) . . ?
N30 C34 C33 107.42(12) . . ?
C21 C34 C33 131.89(12) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.57(13) . . ?
C3 C2 H2 120.2 . . ?
C16 C15 C14 165.61(14) . . ?
O13 C14 C15 108.89(11) . . ?
O13 C14 H14A 109.9 . . ?
O13 C14 H14B 109.9 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O18 C17 H17A 109.9 . . ?
O18 C17 H17B 109.9 . . ?
O18 C17 C16 109.02(11) . . ?
H17A C17 H17B 108.3 . . ?
C16 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
C15 C16 C17 168.12(14) . . ?
C34 C33 H33 126.3 . . ?
C32 C33 C34 107.39(13) . . ?
C32 C33 H33 126.3 . . ?
O19 C20 H20A 109.5 . . ?
O19 C20 H20B 109.5 . . ?
O19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.36(13) . . ?
C2 C3 H3 119.8 . . ?
N26 C25 H25 125.0 . . ?
N26 C25 C24 109.96(12) . . ?
C24 C25 H25 125.0 . . ?
C33 C32 H32 126.6 . . ?
C33 C32 C31 106.84(13) . . ?
C31 C32 H32 126.6 . . ?
C23 C24 C25 107.37(13) . . ?
C23 C24 H24 126.3 . . ?
C25 C24 H24 126.3 . . ?
N30 C31 C32 110.64(13) . . ?
N30 C31 H31 124.7 . . ?
C32 C31 H31 124.7 . . ?
N26 B27 N30 103.6(2) . . ?
F28 B27 N26 107.5(3) . . ?
F28 B27 N30 110.7(3) . . ?
F29 B27 N26 111.1(3) . . ?
F29 B27 N30 110.4(3) . . ?
F29 B27 F28 113.1(3) . . ?
N26 B127 N30 109.2(6) . . ?
F129 B127 N26 112.7(6) . . ?
F129 B127 N30 113.0(7) . . ?
F128 B127 N26 109.8(7) . . ?
F128 B127 N30 104.6(6) . . ?
F128 B127 F129 107.2(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_021RCK17
_database_code_depnum_ccdc_archive 'CCDC 1852222'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C18 H14 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.31
_chemical_oxdiff_usercomment     
'021RCK17 coliurless block 0.2 0.15 0.12 chcl3/hex Cu150K 4x4'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z
3 -x,-y,-z
4 x-1/2,-y,z
5 x+1/2,y+1/2,z+1/2
6 -x+1,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z+1/2
8 x,-y+1/2,z+1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   18.8350(8)
_cell_length_b                   7.1072(3)
_cell_length_c                   21.7952(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.284(4)
_cell_angle_gamma                90
_cell_volume                     2814.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6733
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      73.1460
_cell_measurement_theta_min      4.1240
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24910
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3135
_exptl_crystal_description       block
_exptl_crystal_F_000             1171.8899
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14083
_diffrn_reflns_theta_full        73.3840
_diffrn_reflns_theta_max         73.38
_diffrn_reflns_theta_min         4.21
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -20.00   1.00    2.79    --  -42.36 -37.00  30.00   95
  2  ω     23.00  97.00   1.00    2.79    --   42.36-125.00-120.00   74
  3  ω     23.00  97.00   1.00    2.79    --   42.36-125.00-180.00   74
  4  ω      1.00  82.00   1.00    2.79    --   42.36 -99.00   0.00   81
  5  ω     31.00 130.00   1.00   11.16    --  106.00 -30.00-120.00   99
  6  ω     31.00 130.00   1.00   11.16    --  106.00 -30.00  60.00   99
  7  ω     35.00 130.00   1.00   11.16    --  106.00 -45.00-120.00   95
  8  ω     94.00 178.00   1.00   11.16    --  106.00 125.00 -30.00   84
  9  ω     35.00 130.00   1.00   11.16    --  106.00 -45.00  90.00   95
 10  ω     36.00 134.00   1.00   11.16    --  106.00 -61.00-150.00   98
 11  ω     25.00 109.00   1.00   11.16    --  106.00 -94.00-120.00   84
 12  ω     94.00 178.00   1.00   11.16    --  106.00 125.00-180.00   84
 13  ω     19.00 178.00   1.00   11.16    --  106.00   0.00   0.00  159
 14  ω   -113.00 -16.00   1.00    2.79    --  -42.36 -57.00 150.00   97
 15  ω   -113.00 -16.00   1.00    2.79    --  -42.36 -57.00 -30.00   97
 16  ω   -116.00 -11.00   1.00    2.79    --  -42.36 -77.00  90.00  105
 17  ω   -116.00 -11.00   1.00    2.79    --  -42.36 -77.00 -90.00  105
 18  ω     61.00 178.00   1.00   11.16    --  106.00  15.00 120.00  117
;
_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      -0.0681883000
_diffrn_orient_matrix_UB_12      -0.0626289000
_diffrn_orient_matrix_UB_13      -0.0522253000
_diffrn_orient_matrix_UB_21      -0.0450658000
_diffrn_orient_matrix_UB_22      0.1611378000
_diffrn_orient_matrix_UB_23      0.0186946000
_diffrn_orient_matrix_UB_31      0.0226424000
_diffrn_orient_matrix_UB_32      0.1308167000
_diffrn_orient_matrix_UB_33      -0.0478289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              -26
_reflns_number_gt                2478
_reflns_number_total             2812
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     I>=2u(I)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3559
_refine_diff_density_min         -0.2452
_refine_diff_density_rms         0.0649
_refine_ls_d_res_high            0.8045
_refine_ls_d_res_low             10.5094
_refine_ls_goodness_of_fit_ref   1.0443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.0443
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+1.1282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1432
_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:
 C14(H14a,H14b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C5(H5), C4(H4), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O13 O 0.67936(6) 0.63039(14) 0.28264(4) 0.0287(3) Uani 1.000000 .
O18 O 0.64318(6) 0.34889(15) 0.44986(5) 0.0313(3) Uani 1.000000 .
O20 O 0.96412(6) 0.22682(19) 0.45048(6) 0.0457(3) Uani 1.000000 .
C6 C 0.63309(8) 0.30022(18) 0.33856(7) 0.0258(3) Uani 1.000000 .
C1 C 0.60184(8) 0.2938(2) 0.38997(7) 0.0286(3) Uani 1.000000 .
C7 C 0.71168(8) 0.35451(19) 0.34755(6) 0.0239(3) Uani 1.000000 .
C12 C 0.76744(8) 0.24263(18) 0.38530(6) 0.0249(3) Uani 1.000000 .
C5 C 0.59006(8) 0.2454(2) 0.27878(7) 0.0296(3) Uani 1.000000 .
C8 C 0.73291(8) 0.51453(19) 0.31968(6) 0.0255(3) Uani 1.000000 .
C11 C 0.84131(8) 0.2862(2) 0.39472(6) 0.0259(3) Uani 1.000000 .
C15 C 0.65128(9) 0.7518(2) 0.37481(7) 0.0345(4) Uani 1.000000 .
C19 C 0.90110(8) 0.1700(2) 0.43659(7) 0.0306(3) Uani 1.000000 .
C3 C 0.48951(9) 0.1694(2) 0.32294(9) 0.0400(4) Uani 1.000000 .
C9 C 0.80678(8) 0.5607(2) 0.32900(6) 0.0294(3) Uani 1.000000 .
C4 C 0.51872(9) 0.1795(2) 0.27109(8) 0.0364(4) Uani 1.000000 .
C10 C 0.86084(8) 0.4475(2) 0.36606(7) 0.0292(3) Uani 1.000000 .
C14 C 0.66849(9) 0.8019(2) 0.31526(7) 0.0327(4) Uani 1.000000 .
C2 C 0.53055(9) 0.2280(2) 0.38227(8) 0.0369(4) Uani 1.000000 .
C16 C 0.64113(10) 0.6712(2) 0.41963(8) 0.0356(4) Uani 1.000000 .
C21 C 0.88109(9) -0.0145(2) 0.46091(8) 0.0361(4) Uani 1.000000 .
C17 C 0.62760(10) 0.5386(2) 0.46672(8) 0.0388(4) Uani 1.000000 .
H9 H 0.81975(8) 0.6682(2) 0.31018(6) 0.0352(4) Uiso 1.000000 R
H10 H 0.91018(8) 0.4783(2) 0.37201(7) 0.0350(4) Uiso 1.000000 R
H12 H 0.75461(8) 0.13593(18) 0.40464(6) 0.0299(4) Uiso 1.000000 R
H5 H 0.60932(8) 0.2530(2) 0.24372(7) 0.0355(4) Uiso 1.000000 R
H4 H 0.49070(9) 0.1422(2) 0.23113(8) 0.0436(5) Uiso 1.000000 R
H3 H 0.44213(9) 0.1231(2) 0.31793(9) 0.0480(5) Uiso 1.000000 R
H2 H 0.51045(9) 0.2234(2) 0.41690(8) 0.0442(5) Uiso 1.000000 R
H14a H 0.71275(9) 0.8781(2) 0.32404(7) 0.0392(4) Uiso 1.000000 R
H14b H 0.62841(9) 0.8744(2) 0.28863(7) 0.0392(4) Uiso 1.000000 R
H21a H 0.92480(12) -0.0750(9) 0.4858(5) 0.0541(6) Uiso 1.000000 GR
H21b H 0.8479(6) 0.0069(3) 0.4869(5) 0.0541(6) Uiso 1.000000 GR
H21c H 0.8578(7) -0.0936(7) 0.42564(8) 0.0541(6) Uiso 1.000000 GR
H17a H 0.57668(10) 0.5475(2) 0.46820(8) 0.0465(5) Uiso 1.000000 R
H17b H 0.65874(10) 0.5697(2) 0.50851(8) 0.0465(5) Uiso 1.000000 R


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
O13 C8 1.3849(16) . ?
O13 C14 1.4526(17) . ?
O18 C1 1.3885(18) . ?
O18 C17 1.4480(19) . ?
O20 C19 1.214(2) . ?
C6 C1 1.397(2) . ?
C6 C7 1.492(2) . ?
C6 C5 1.3963(19) . ?
C1 C2 1.390(2) . ?
C7 C12 1.3988(18) . ?
C7 C8 1.396(2) . ?
C12 C11 1.387(2) . ?
C12 H12 0.9300 . ?
C5 C4 1.391(2) . ?
C5 H5 0.9300 . ?
C8 C9 1.391(2) . ?
C11 C19 1.4973(19) . ?
C11 C10 1.400(2) . ?
C15 C14 1.462(2) . ?
C15 C16 1.191(2) . ?
C19 C21 1.499(2) . ?
C3 C4 1.383(3) . ?
C3 C2 1.384(2) . ?
C3 H3 0.9300 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10 0.9300 . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
C2 H2 0.9300 . ?
C16 C17 1.464(2) . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?
C17 H17a 0.9700 . ?
C17 H17b 0.9700 . ?

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
C14 O13 C8 112.87(10) . . ?
C17 O18 C1 113.60(11) . . ?
C7 C6 C1 121.10(12) . . ?
C5 C6 C1 118.39(14) . . ?
C5 C6 C7 120.44(14) . . ?
C6 C1 O18 119.62(13) . . ?
C2 C1 O18 119.55(14) . . ?
C2 C1 C6 120.81(14) . . ?
C12 C7 C6 119.70(12) . . ?
C8 C7 C6 122.78(12) . . ?
C8 C7 C12 117.52(13) . . ?
C11 C12 C7 121.90(13) . . ?
H12 C12 C7 119.05(8) . . ?
H12 C12 C11 119.05(8) . . ?
C4 C5 C6 120.76(15) . . ?
H5 C5 C6 119.62(9) . . ?
H5 C5 C4 119.62(10) . . ?
C7 C8 O13 119.33(13) . . ?
C9 C8 O13 119.44(12) . . ?
C9 C8 C7 121.23(12) . . ?
C19 C11 C12 122.07(13) . . ?
C10 C11 C12 119.22(12) . . ?
C10 C11 C19 118.68(13) . . ?
C16 C15 C14 165.13(16) . . ?
C11 C19 O20 119.81(14) . . ?
C21 C19 O20 121.55(13) . . ?
C21 C19 C11 118.64(13) . . ?
C2 C3 C4 120.22(15) . . ?
H3 C3 C4 119.89(9) . . ?
H3 C3 C2 119.89(11) . . ?
C10 C9 C8 120.24(13) . . ?
H9 C9 C8 119.88(8) . . ?
H9 C9 C10 119.88(9) . . ?
C3 C4 C5 119.91(14) . . ?
H4 C4 C5 120.05(10) . . ?
H4 C4 C3 120.05(9) . . ?
C9 C10 C11 119.89(13) . . ?
H10 C10 C11 120.05(8) . . ?
H10 C10 C9 120.05(9) . . ?
C15 C14 O13 108.83(12) . . ?
H14a C14 O13 109.92(8) . . ?
H14a C14 C15 109.92(9) . . ?
H14b C14 O13 109.92(7) . . ?
H14b C14 C15 109.92(9) . . ?
H14b C14 H14a 108.3 . . ?
C3 C2 C1 119.87(16) . . ?
H2 C2 C1 120.07(10) . . ?
H2 C2 C3 120.07(11) . . ?
C17 C16 C15 168.55(16) . . ?
H21a C21 C19 109.5 . . ?
H21b C21 C19 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C19 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C16 C17 O18 109.68(13) . . ?
H17a C17 O18 109.73(9) . . ?
H17a C17 C16 109.73(10) . . ?
H17b C17 O18 109.73(8) . . ?
H17b C17 C16 109.73(9) . . ?
H17b C17 H17a 108.2 . . ?

_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 4.837
_oxdiff_exptl_absorpt_empirical_full_min 0.423
