# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1b
_audit_block_doi                 10.5517/ccdc.csd.cc1nsd50
_database_code_depnum_ccdc_archive 'CCDC 1542782'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H19 N O2'
_chemical_formula_sum            'C26 H19 N O2'
_chemical_formula_weight         377.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1B1
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.65703(12)
_cell_length_b                   9.51508(16)
_cell_length_c                   26.1253(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1903.42(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3749
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0260
_cell_measurement_theta_min      4.9240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83793
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5060
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.346
_diffrn_reflns_theta_min         4.947
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  32.00   1.00    1.00    --  -41.49  37.00 -30.00   98
  2  ω    -32.00  -5.00   1.00    1.00    --  -41.49 125.00 -30.00   27
  3  ω     83.00 174.00   1.00    1.00    --  107.52  45.00  90.00   91
  4  ω    109.00 176.00   1.00    1.00    --  107.52 125.00  90.00   67
  5  ω     83.00 140.00   1.00    1.00    --  107.52 -77.00 -60.00   57
  6  ω     54.00 114.00   1.00    1.00    --  107.52-125.00 -90.00   60
  7  ω     30.00  76.00   1.00    1.00    --   41.49-125.00 -60.00   46
;
_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      0.0961333000
_diffrn_orient_matrix_UB_12      0.0528772000
_diffrn_orient_matrix_UB_13      -0.0481138000
_diffrn_orient_matrix_UB_21      0.1725594000
_diffrn_orient_matrix_UB_22      0.0046699000
_diffrn_orient_matrix_UB_23      0.0302603000
_diffrn_orient_matrix_UB_31      0.0384374000
_diffrn_orient_matrix_UB_32      -0.1529268000
_diffrn_orient_matrix_UB_33      -0.0157014000
_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         0.533
_reflns_Friedel_fraction_full    0.767
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                3192
_reflns_number_total             3309
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.46 (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.090
_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)+(0.0356P)²+0.2784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0710
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.82289(16) 0.49253(12) 0.66606(5) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.60015(15) 0.34423(12) 0.64722(5) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.56187(18) 0.58317(15) 0.64358(5) 0.0140(3) Uani 1 1 d . . . . .
C1 C 0.6296(2) 0.72025(17) 0.65459(6) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.7824(2) 0.76974(18) 0.63232(6) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.8443 0.7141 0.6093 0.020 Uiso 1 1 calc R . . . .
C3 C 0.8418(2) 0.90383(19) 0.64488(7) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.9447 0.9373 0.6304 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7491(2) 0.98804(19) 0.67877(7) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.7889 1.0778 0.6866 0.023 Uiso 1 1 calc R . . . .
C5 C 0.5972(2) 0.93772(18) 0.70074(6) 0.0181(4) Uani 1 1 d . . . . .
H5 H 0.5354 0.9940 0.7235 0.022 Uiso 1 1 calc R . . . .
C6 C 0.5357(2) 0.80307(18) 0.68911(6) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.3745(2) 0.74724(18) 0.71107(6) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.3291 0.7867 0.7408 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2924(2) 0.64029(19) 0.68879(6) 0.0165(3) Uani 1 1 d . . . . .
H8 H 0.1874 0.6080 0.7023 0.020 Uiso 1 1 calc R . . . .
C9 C 0.3680(2) 0.57071(18) 0.64168(6) 0.0141(3) Uani 1 1 d . . . . .
H9 H 0.3390 0.4705 0.6434 0.017 Uiso 1 1 calc R . . . .
C10 C 0.2904(2) 0.62901(18) 0.59196(6) 0.0145(3) Uani 1 1 d . . . . .
C11 C 0.2320(2) 0.76560(19) 0.58967(7) 0.0173(4) Uani 1 1 d . . . . .
H11 H 0.2466 0.8235 0.6180 0.021 Uiso 1 1 calc R . . . .
C12 C 0.1503(2) 0.82041(19) 0.54547(6) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.1177 0.9145 0.5443 0.025 Uiso 1 1 calc R . . . .
C13 C 0.1193(2) 0.7353(2) 0.50445(7) 0.0199(4) Uani 1 1 d . . . . .
H13 H 0.0600 0.7704 0.4761 0.024 Uiso 1 1 calc R . . . .
C14 C 0.1770(2) 0.59377(19) 0.50472(6) 0.0168(3) Uani 1 1 d . . . . .
C15 C 0.1441(2) 0.50384(19) 0.46229(6) 0.0195(4) Uani 1 1 d . . . . .
H15 H 0.0777 0.5366 0.4350 0.023 Uiso 1 1 calc R . . . .
C16 C 0.2086(2) 0.3702(2) 0.46104(7) 0.0222(4) Uani 1 1 d . . . . .
H16 H 0.1863 0.3125 0.4331 0.027 Uiso 1 1 calc R . . . .
C17 C 0.3093(2) 0.31992(19) 0.50241(7) 0.0222(4) Uani 1 1 d . . . . .
H17 H 0.3564 0.2299 0.5010 0.027 Uiso 1 1 calc R . . . .
C18 C 0.3387(2) 0.40220(19) 0.54468(6) 0.0180(3) Uani 1 1 d . . . . .
H18 H 0.4042 0.3667 0.5717 0.022 Uiso 1 1 calc R . . . .
C19 C 0.2707(2) 0.54062(18) 0.54778(6) 0.0153(3) Uani 1 1 d . . . . .
C20 C 0.6550(2) 0.46232(18) 0.65158(6) 0.0149(3) Uani 1 1 d . . . . .
C21 C 0.9385(2) 0.37832(17) 0.66908(7) 0.0160(3) Uani 1 1 d . . . . .
C22 C 0.9961(2) 0.31332(18) 0.62490(7) 0.0200(4) Uani 1 1 d . . . . .
H22 H 0.9539 0.3408 0.5931 0.024 Uiso 1 1 calc R . . . .
C23 C 1.1184(2) 0.20611(19) 0.62907(8) 0.0247(4) Uani 1 1 d . . . . .
H23 H 1.1582 0.1608 0.5998 0.030 Uiso 1 1 calc R . . . .
C24 C 1.1815(2) 0.1662(2) 0.67667(8) 0.0278(4) Uani 1 1 d . . . . .
H24 H 1.2630 0.0942 0.6792 0.033 Uiso 1 1 calc R . . . .
C25 C 1.1231(2) 0.2336(2) 0.72038(8) 0.0251(4) Uani 1 1 d . . . . .
H25 H 1.1656 0.2068 0.7523 0.030 Uiso 1 1 calc R . . . .
C26 C 1.0010(2) 0.34142(19) 0.71667(7) 0.0188(4) Uani 1 1 d . . . . .
H26 H 0.9623 0.3879 0.7459 0.023 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
O1 C20 1.370(2) . ?
O1 C21 1.404(2) . ?
O2 C20 1.205(2) . ?
N1 C1 1.433(2) . ?
N1 C9 1.4897(19) . ?
N1 C20 1.369(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C6 C7 1.461(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.330(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.513(2) . ?
C9 H9 0.9800 . ?
C9 C10 1.532(2) . ?
C10 C11 1.376(2) . ?
C10 C19 1.436(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.413(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.417(3) . ?
C14 C15 1.423(2) . ?
C14 C19 1.427(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.364(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.411(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.419(2) . ?
C21 C22 1.382(2) . ?
C21 C26 1.378(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.391(3) . ?
C26 H26 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
C20 O1 C21 116.40(13) . . ?
C1 N1 C9 116.09(13) . . ?
C20 N1 C1 123.04(13) . . ?
C20 N1 C9 117.20(14) . . ?
C2 C1 N1 121.97(15) . . ?
C2 C1 C6 120.86(15) . . ?
C6 C1 N1 117.16(15) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.12(16) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.74(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.66(16) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.71(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.90(15) . . ?
C1 C6 C7 118.91(15) . . ?
C5 C6 C7 122.18(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.37(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.64(15) . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C8 108.64(13) . . ?
N1 C9 H9 107.6 . . ?
N1 C9 C10 112.71(13) . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 112.49(13) . . ?
C10 C9 H9 107.6 . . ?
C11 C10 C9 120.33(15) . . ?
C11 C10 C19 118.97(15) . . ?
C19 C10 C9 120.65(15) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.88(16) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.00(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.39(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.83(15) . . ?
C13 C14 C19 119.83(16) . . ?
C15 C14 C19 119.34(16) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.01(16) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.70(17) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.83(17) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.03(16) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C10 118.60(16) . . ?
C18 C19 C10 123.46(15) . . ?
C18 C19 C14 117.94(15) . . ?
O2 C20 O1 123.27(15) . . ?
O2 C20 N1 125.96(15) . . ?
N1 C20 O1 110.77(14) . . ?
C22 C21 O1 120.05(15) . . ?
C26 C21 O1 117.86(15) . . ?
C26 C21 C22 121.92(15) . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C23 118.58(16) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.39(17) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.06(17) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.07(17) . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 118.97(16) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C21 C22 C23 176.21(15) . . . . ?
O1 C21 C26 C25 -176.51(15) . . . . ?
N1 C1 C2 C3 -179.64(15) . . . . ?
N1 C1 C6 C5 -179.81(14) . . . . ?
N1 C1 C6 C7 -1.0(2) . . . . ?
N1 C9 C10 C11 -93.97(18) . . . . ?
N1 C9 C10 C19 88.62(18) . . . . ?
C1 N1 C9 C8 -48.53(18) . . . . ?
C1 N1 C9 C10 76.84(18) . . . . ?
C1 N1 C20 O1 -6.2(2) . . . . ?
C1 N1 C20 O2 173.27(16) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C6 C7 C8 -18.8(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 179.24(15) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -179.14(16) . . . . ?
C5 C6 C7 C8 159.92(16) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C6 C7 C8 C9 2.6(2) . . . . ?
C7 C8 C9 N1 29.5(2) . . . . ?
C7 C8 C9 C10 -95.96(18) . . . . ?
C8 C9 C10 C11 29.3(2) . . . . ?
C8 C9 C10 C19 -148.13(15) . . . . ?
C9 N1 C1 C2 -144.39(15) . . . . ?
C9 N1 C1 C6 35.9(2) . . . . ?
C9 N1 C20 O1 -163.73(13) . . . . ?
C9 N1 C20 O2 15.7(2) . . . . ?
C9 C10 C11 C12 -176.22(15) . . . . ?
C9 C10 C19 C14 171.80(14) . . . . ?
C9 C10 C19 C18 -7.8(2) . . . . ?
C10 C11 C12 C13 3.4(3) . . . . ?
C11 C10 C19 C14 -5.6(2) . . . . ?
C11 C10 C19 C18 174.80(15) . . . . ?
C11 C12 C13 C14 -3.4(3) . . . . ?
C12 C13 C14 C15 179.52(16) . . . . ?
C12 C13 C14 C19 -1.1(2) . . . . ?
C13 C14 C15 C16 175.95(16) . . . . ?
C13 C14 C19 C10 5.6(2) . . . . ?
C13 C14 C19 C18 -174.80(15) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C14 C19 C10 -174.98(15) . . . . ?
C15 C14 C19 C18 4.6(2) . . . . ?
C15 C16 C17 C18 2.1(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C10 177.01(17) . . . . ?
C17 C18 C19 C14 -2.6(2) . . . . ?
C19 C10 C11 C12 1.2(2) . . . . ?
C19 C14 C15 C16 -3.5(2) . . . . ?
C20 O1 C21 C22 71.4(2) . . . . ?
C20 O1 C21 C26 -113.36(17) . . . . ?
C20 N1 C1 C2 57.8(2) . . . . ?
C20 N1 C1 C6 -121.92(17) . . . . ?
C20 N1 C9 C8 110.61(16) . . . . ?
C20 N1 C9 C10 -124.03(15) . . . . ?
C21 O1 C20 O2 8.5(2) . . . . ?
C21 O1 C20 N1 -172.07(13) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C21 C26 C25 -1.3(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C25 C26 C21 0.7(3) . . . . ?
C26 C21 C22 C23 1.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.532
####################################################################### 
# 
# 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_2a
_audit_block_doi                 10.5517/ccdc.csd.cc1nsd72
_database_code_depnum_ccdc_archive 'CCDC 1542784'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_audit_creation_date             2017-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H30 B N O4'
_chemical_formula_sum            'C27 H30 B N O4'
_chemical_formula_weight         443.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1B1O1
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.52078(10)
_cell_length_b                   15.6118(2)
_cell_length_c                   17.5200(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2330.58(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7541
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1500
_cell_measurement_theta_min      5.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67732
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9699
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.363
_diffrn_reflns_theta_min         3.792
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  32.00   1.00    1.00    --  -41.49  57.00 -90.00   94
  2  ω    -22.00   5.00   1.00    1.00    --   41.49 -48.00-127.00   27
  3  ω     42.00  68.00   1.00    1.00    --   41.49 -48.00-127.00   26
  4  ω    121.00 175.00   1.00    1.00    --  107.52  30.00-180.00   54
  5  ω     86.00 173.00   1.00    1.00    --  107.52  61.00-150.00   87
  6  ω     75.00 159.00   1.00    1.00    --  107.52  77.00 -60.00   84
  7  ω     97.00 154.00   1.00    1.00    --  107.52 125.00  60.00   57
  8  ω     42.00 137.00   1.00    1.00    --  107.52 -61.00  60.00   95
  9  ω     27.00  98.00   1.00    1.00    --  107.52 -94.00  60.00   71
 10  ω     24.00  51.00   1.00    1.00    --   41.49-125.00  90.00   27
 11  ω    -60.00  13.00   1.00    1.00    --  -41.49  37.00-180.00   73
;
_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      -0.1128988000
_diffrn_orient_matrix_UB_12      -0.0689633000
_diffrn_orient_matrix_UB_13      0.0307967000
_diffrn_orient_matrix_UB_21      -0.1375990000
_diffrn_orient_matrix_UB_22      0.0439150000
_diffrn_orient_matrix_UB_23      -0.0412120000
_diffrn_orient_matrix_UB_31      0.0310731000
_diffrn_orient_matrix_UB_32      -0.0554650000
_diffrn_orient_matrix_UB_33      -0.0712547000
_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         0.670
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                4277
_reflns_number_total             4390
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.46 (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.062
_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)+(0.0406P)²+0.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0802
_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:
 C7(H7), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20), C21(H21),
 C23(H23), C24(H24), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C16(H16A,
 H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.66759(17) 0.69340(9) 0.67728(9) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.8087(2) 0.62441(10) 0.58670(9) 0.0344(4) Uani 1 1 d . . . . .
O3 O 1.02071(15) 0.46444(10) 0.71789(7) 0.0236(3) Uani 1 1 d . . . . .
O4 O 0.95049(15) 0.42570(9) 0.59854(7) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.76032(17) 0.45509(10) 0.68311(9) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.9005(3) 0.73055(17) 0.74508(12) 0.0345(5) Uani 1 1 d . . . . .
H1A H 0.8377 0.7506 0.7869 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.9972 0.7620 0.7435 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.9225 0.6707 0.7518 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.8122(2) 0.74362(12) 0.67115(11) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.7636(3) 0.83647(14) 0.66265(15) 0.0352(5) Uani 1 1 d . . . . .
H3A H 0.6946 0.8422 0.6196 0.053 Uiso 1 1 calc GR . . . .
H3B H 0.8551 0.8713 0.6549 0.053 Uiso 1 1 calc GR . . . .
H3C H 0.7103 0.8548 0.7081 0.053 Uiso 1 1 calc GR . . . .
C4 C 0.8968(2) 0.70307(12) 0.59996(11) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.8886(4) 0.75590(18) 0.52800(13) 0.0431(6) Uani 1 1 d . . . . .
H5A H 0.9314 0.7237 0.4862 0.065 Uiso 1 1 calc GR . . . .
H5B H 0.9481 0.8076 0.5347 0.065 Uiso 1 1 calc GR . . . .
H5C H 0.7812 0.7701 0.5173 0.065 Uiso 1 1 calc GR . . . .
C6 C 1.0662(3) 0.67650(18) 0.61386(15) 0.0400(6) Uani 1 1 d . . . . .
H6A H 1.0707 0.6383 0.6567 0.060 Uiso 1 1 calc GR . . . .
H6B H 1.1284 0.7264 0.6243 0.060 Uiso 1 1 calc GR . . . .
H6C H 1.1062 0.6481 0.5693 0.060 Uiso 1 1 calc GR . . . .
C7 C 0.5572(2) 0.54771(11) 0.63095(10) 0.0166(4) Uani 1 1 d . . . . .
H7 H 0.4850 0.5556 0.5880 0.020 Uiso 1 1 calc R . . . .
C8 C 0.4610(2) 0.54129(12) 0.70476(10) 0.0188(4) Uani 1 1 d . . . . .
H8A H 0.4217 0.5976 0.7182 0.023 Uiso 1 1 calc R . . . .
H8B H 0.3714 0.5042 0.6962 0.023 Uiso 1 1 calc R . . . .
C9 C 0.5569(2) 0.50649(11) 0.77030(10) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.4982(2) 0.51175(13) 0.84480(11) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.4050 0.5412 0.8534 0.026 Uiso 1 1 calc R . . . .
C11 C 0.5745(2) 0.47456(13) 0.90586(11) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.5338 0.4795 0.9549 0.029 Uiso 1 1 calc R . . . .
C12 C 0.7130(2) 0.42967(13) 0.89320(11) 0.0228(4) Uani 1 1 d . . . . .
H12 H 0.7638 0.4029 0.9337 0.027 Uiso 1 1 calc R . . . .
C13 C 0.7751(2) 0.42476(13) 0.82055(11) 0.0203(4) Uani 1 1 d . . . . .
H13 H 0.8680 0.3949 0.8124 0.024 Uiso 1 1 calc R . . . .
C14 C 0.6995(2) 0.46433(12) 0.75899(10) 0.0165(4) Uani 1 1 d . . . . .
C15 C 0.9195(2) 0.44999(12) 0.67091(10) 0.0162(4) Uani 1 1 d . . . . .
C16 C 1.1148(2) 0.41827(16) 0.58035(12) 0.0266(5) Uani 1 1 d . . . . .
H16A H 1.1263 0.3960 0.5296 0.040 Uiso 1 1 calc GR . . . .
H16B H 1.1643 0.3802 0.6160 0.040 Uiso 1 1 calc GR . . . .
H16C H 1.1633 0.4737 0.5833 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.6516(2) 0.46416(12) 0.61813(10) 0.0148(3) Uani 1 1 d . . . . .
H17 H 0.7162 0.4730 0.5725 0.018 Uiso 1 1 calc R . . . .
C18 C 0.5540(2) 0.38411(11) 0.60405(10) 0.0150(3) Uani 1 1 d . . . . .
C19 C 0.5344(2) 0.32167(12) 0.65886(10) 0.0177(4) Uani 1 1 d . . . . .
H19 H 0.5763 0.3303 0.7073 0.021 Uiso 1 1 calc R . . . .
C20 C 0.4525(2) 0.24502(12) 0.64349(11) 0.0201(4) Uani 1 1 d . . . . .
H20 H 0.4415 0.2040 0.6816 0.024 Uiso 1 1 calc R . . . .
C21 C 0.3893(2) 0.23085(12) 0.57295(11) 0.0202(4) Uani 1 1 d . . . . .
H21 H 0.3357 0.1801 0.5632 0.024 Uiso 1 1 calc R . . . .
C22 C 0.4052(2) 0.29316(12) 0.51469(11) 0.0174(4) Uani 1 1 d . . . . .
C23 C 0.3386(2) 0.27997(13) 0.44140(11) 0.0206(4) Uani 1 1 d . . . . .
H23 H 0.2841 0.2295 0.4315 0.025 Uiso 1 1 calc R . . . .
C24 C 0.3529(2) 0.33989(13) 0.38528(11) 0.0210(4) Uani 1 1 d . . . . .
H24 H 0.3064 0.3307 0.3380 0.025 Uiso 1 1 calc R . . . .
C25 C 0.4381(2) 0.41593(13) 0.39877(11) 0.0201(4) Uani 1 1 d . . . . .
H25 H 0.4502 0.4560 0.3599 0.024 Uiso 1 1 calc R . . . .
C26 C 0.5031(2) 0.43082(12) 0.46907(10) 0.0178(4) Uani 1 1 d . . . . .
H26 H 0.5584 0.4813 0.4773 0.021 Uiso 1 1 calc R . . . .
C27 C 0.4879(2) 0.37092(12) 0.52984(10) 0.0151(3) Uani 1 1 d . . . . .
B1 B 0.6785(2) 0.62448(14) 0.63153(11) 0.0172(4) Uani 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 C2 1.464(2) . ?
O1 B1 1.345(3) . ?
O2 C4 1.458(2) . ?
O2 B1 1.359(3) . ?
O3 C15 1.213(2) . ?
O4 C15 1.350(2) . ?
O4 C16 1.441(2) . ?
N1 C14 1.434(2) . ?
N1 C15 1.375(2) . ?
N1 C17 1.474(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.512(3) . ?
C2 C3 1.515(3) . ?
C2 C4 1.574(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.508(3) . ?
C4 C6 1.521(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.534(3) . ?
C7 C17 1.549(2) . ?
C7 B1 1.583(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(3) . ?
C9 C10 1.400(3) . ?
C9 C14 1.396(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.521(2) . ?
C18 C19 1.379(3) . ?
C18 C27 1.432(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.411(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.417(3) . ?
C22 C23 1.419(3) . ?
C22 C27 1.429(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.363(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.411(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.370(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.423(3) . ?

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
B1 O1 C2 109.05(15) . . ?
B1 O2 C4 109.10(16) . . ?
C15 O4 C16 114.88(15) . . ?
C14 N1 C17 118.62(14) . . ?
C15 N1 C14 120.41(15) . . ?
C15 N1 C17 120.34(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 106.47(17) . . ?
O1 C2 C3 106.83(16) . . ?
O1 C2 C4 103.19(14) . . ?
C1 C2 C3 110.45(18) . . ?
C1 C2 C4 113.39(16) . . ?
C3 C2 C4 115.61(18) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C2 103.27(15) . . ?
O2 C4 C5 107.69(18) . . ?
O2 C4 C6 106.50(18) . . ?
C5 C4 C2 114.93(18) . . ?
C5 C4 C6 109.1(2) . . ?
C6 C4 C2 114.67(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 H7 108.7 . . ?
C8 C7 C17 110.17(15) . . ?
C8 C7 B1 113.14(15) . . ?
C17 C7 H7 108.7 . . ?
C17 C7 B1 107.40(15) . . ?
B1 C7 H7 108.7 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.03(15) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 119.62(17) . . ?
C14 C9 C8 122.18(16) . . ?
C14 C9 C10 118.09(17) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.99(18) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.22(18) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.02(19) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.63(18) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 N1 119.58(16) . . ?
C9 C14 C13 119.94(17) . . ?
C13 C14 N1 120.23(16) . . ?
O3 C15 O4 123.40(16) . . ?
O3 C15 N1 125.80(17) . . ?
O4 C15 N1 110.81(15) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C7 107.17(14) . . ?
N1 C17 H17 106.9 . . ?
N1 C17 C18 112.94(15) . . ?
C7 C17 H17 106.9 . . ?
C18 C17 C7 115.54(14) . . ?
C18 C17 H17 106.9 . . ?
C19 C18 C17 122.29(16) . . ?
C19 C18 C27 118.90(16) . . ?
C27 C18 C17 118.71(15) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.77(17) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.33(17) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.20(18) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C23 120.94(17) . . ?
C21 C22 C27 119.79(17) . . ?
C23 C22 C27 119.26(17) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.16(18) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.18(17) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.06(18) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.64(17) . . ?
C27 C26 H26 119.2 . . ?
C22 C27 C18 119.01(16) . . ?
C26 C27 C18 123.32(16) . . ?
C26 C27 C22 117.65(16) . . ?
O1 B1 O2 113.67(18) . . ?
O1 B1 C7 124.36(17) . . ?
O2 B1 C7 121.92(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C4 O2 -12.62(19) . . . . ?
O1 C2 C4 C5 104.4(2) . . . . ?
O1 C2 C4 C6 -128.05(18) . . . . ?
N1 C17 C18 C19 18.6(2) . . . . ?
N1 C17 C18 C27 -157.68(14) . . . . ?
C1 C2 C4 O2 102.13(19) . . . . ?
C1 C2 C4 C5 -140.9(2) . . . . ?
C1 C2 C4 C6 -13.3(3) . . . . ?
C2 O1 B1 O2 -6.7(2) . . . . ?
C2 O1 B1 C7 170.81(17) . . . . ?
C3 C2 C4 O2 -128.85(18) . . . . ?
C3 C2 C4 C5 -11.9(3) . . . . ?
C3 C2 C4 C6 115.7(2) . . . . ?
C4 O2 B1 O1 -2.3(2) . . . . ?
C4 O2 B1 C7 -179.90(17) . . . . ?
C7 C8 C9 C10 167.67(16) . . . . ?
C7 C8 C9 C14 -16.2(2) . . . . ?
C7 C17 C18 C19 -105.3(2) . . . . ?
C7 C17 C18 C27 78.43(19) . . . . ?
C8 C7 C17 N1 -61.84(18) . . . . ?
C8 C7 C17 C18 65.02(19) . . . . ?
C8 C7 B1 O1 -21.0(3) . . . . ?
C8 C7 B1 O2 156.38(18) . . . . ?
C8 C9 C10 C11 174.35(17) . . . . ?
C8 C9 C14 N1 1.6(3) . . . . ?
C8 C9 C14 C13 -172.72(18) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C9 C14 N1 177.80(17) . . . . ?
C10 C9 C14 C13 3.5(3) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 N1 -176.69(17) . . . . ?
C12 C13 C14 C9 -2.4(3) . . . . ?
C14 N1 C15 O3 -11.0(3) . . . . ?
C14 N1 C15 O4 168.55(16) . . . . ?
C14 N1 C17 C7 49.2(2) . . . . ?
C14 N1 C17 C18 -79.21(19) . . . . ?
C14 C9 C10 C11 -2.0(3) . . . . ?
C15 N1 C14 C9 151.28(17) . . . . ?
C15 N1 C14 C13 -34.5(3) . . . . ?
C15 N1 C17 C7 -121.80(18) . . . . ?
C15 N1 C17 C18 109.83(18) . . . . ?
C16 O4 C15 O3 -0.2(3) . . . . ?
C16 O4 C15 N1 -179.80(17) . . . . ?
C17 N1 C14 C9 -19.7(2) . . . . ?
C17 N1 C14 C13 154.59(17) . . . . ?
C17 N1 C15 O3 159.80(18) . . . . ?
C17 N1 C15 O4 -20.7(2) . . . . ?
C17 C7 C8 C9 46.1(2) . . . . ?
C17 C7 B1 O1 -142.78(19) . . . . ?
C17 C7 B1 O2 34.6(2) . . . . ?
C17 C18 C19 C20 -175.63(16) . . . . ?
C17 C18 C27 C22 175.77(15) . . . . ?
C17 C18 C27 C26 -2.8(2) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C18 C27 C22 -0.6(2) . . . . ?
C19 C18 C27 C26 -179.21(17) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C23 -179.19(17) . . . . ?
C20 C21 C22 C27 0.1(3) . . . . ?
C21 C22 C23 C24 179.69(18) . . . . ?
C21 C22 C27 C18 0.3(2) . . . . ?
C21 C22 C27 C26 178.91(16) . . . . ?
C22 C23 C24 C25 1.4(3) . . . . ?
C23 C22 C27 C18 179.60(16) . . . . ?
C23 C22 C27 C26 -1.7(2) . . . . ?
C23 C24 C25 C26 -1.8(3) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C26 C27 C18 179.99(17) . . . . ?
C25 C26 C27 C22 1.4(3) . . . . ?
C27 C18 C19 C20 0.6(3) . . . . ?
C27 C22 C23 C24 0.4(3) . . . . ?
B1 O1 C2 C1 -107.70(19) . . . . ?
B1 O1 C2 C3 134.26(18) . . . . ?
B1 O1 C2 C4 11.9(2) . . . . ?
B1 O2 C4 C2 9.4(2) . . . . ?
B1 O2 C4 C5 -112.6(2) . . . . ?
B1 O2 C4 C6 130.56(19) . . . . ?
B1 C7 C8 C9 -74.1(2) . . . . ?
B1 C7 C17 N1 61.80(17) . . . . ?
B1 C7 C17 C18 -171.35(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.546
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_2p
_audit_block_doi                 10.5517/ccdc.csd.cc1nsd61
_database_code_depnum_ccdc_archive 'CCDC 1542783'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H32 B N O6'
_chemical_formula_sum            'C25 H32 B N O6'
_chemical_formula_weight         453.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c1h1n1o1B1
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.0936(3)
_cell_length_b                   14.6662(2)
_cell_length_c                   14.7500(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2399.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1360
_cell_measurement_theta_min      4.9710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69659
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7673
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.281
_diffrn_reflns_theta_min         4.251
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  10.00   1.00    2.00    --  -41.49   0.00-150.00  116
  2  ω     27.00 109.00   1.00   10.00    --  107.52 -94.00-150.00   82
  3  ω     82.00 170.00   1.00   10.00    --  107.52  30.00  90.00   88
  4  ω     78.00 176.00   1.00   10.00    --  107.52  77.00 150.00   98
  5  ω     26.00  52.00   1.00    2.00    --   41.74-125.00 -60.00   26
  6  ω     31.00  72.00   1.00    2.00    --   41.74-125.00 150.00   41
  7  ω    140.00 178.00   1.00   10.00    --  107.52  77.00  60.00   38
  8  ω    135.00 162.00   1.00   10.00    --  107.52 125.00-150.00   27
  9  ω    122.00 148.00   1.00   10.00    --  107.52  77.00 -60.00   26
;
_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      -0.0771509000
_diffrn_orient_matrix_UB_12      0.0330613000
_diffrn_orient_matrix_UB_13      -0.0804254000
_diffrn_orient_matrix_UB_21      -0.0952958000
_diffrn_orient_matrix_UB_22      -0.0731037000
_diffrn_orient_matrix_UB_23      0.0222598000
_diffrn_orient_matrix_UB_31      -0.0651283000
_diffrn_orient_matrix_UB_32      0.0677539000
_diffrn_orient_matrix_UB_33      0.0628998000
_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         0.618
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                4025
_reflns_number_total             4326
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.46 (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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.061
_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)+(0.0388P)²+0.2235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0858
_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:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.24272(15) 0.32904(11) 0.87204(11) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.17958(16) 0.37393(11) 0.17191(11) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.55134(16) 0.16699(10) 0.43534(11) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.48040(15) 0.09960(10) 0.56269(12) 0.0204(3) Uani 1 1 d . . . . .
O5 O 0.67208(15) 0.48138(10) 0.43862(11) 0.0176(3) Uani 1 1 d . . . . .
O6 O 0.52164(14) 0.58506(10) 0.46427(11) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.45918(17) 0.25386(12) 0.53853(13) 0.0153(4) Uani 1 1 d . . . . .
C1 C 0.4884(2) 0.33035(14) 0.47626(15) 0.0150(4) Uani 1 1 d . . . . .
H1 H 0.5709 0.3213 0.4544 0.018 Uiso 1 1 calc R . . . .
C2 C 0.4839(2) 0.42272(14) 0.52556(15) 0.0152(4) Uani 1 1 d . . . . .
H2 H 0.3997 0.4430 0.5275 0.018 Uiso 1 1 calc R . . . .
C3 C 0.5285(2) 0.41078(15) 0.62414(15) 0.0162(4) Uani 1 1 d . . . . .
H3A H 0.6080 0.3832 0.6249 0.019 Uiso 1 1 calc R . . . .
H3B H 0.5329 0.4694 0.6545 0.019 Uiso 1 1 calc R . . . .
C4 C 0.4388(2) 0.34992(14) 0.67060(15) 0.0156(4) Uani 1 1 d . . . . .
C5 C 0.3855(2) 0.37211(15) 0.75341(15) 0.0170(4) Uani 1 1 d . . . . .
H5 H 0.4081 0.4251 0.7836 0.020 Uiso 1 1 calc R . . . .
C6 C 0.2984(2) 0.31493(15) 0.79077(15) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.2626(2) 0.23638(15) 0.74382(16) 0.0185(4) Uani 1 1 d . . . . .
H7 H 0.2050 0.1980 0.7690 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3126(2) 0.21540(15) 0.65990(16) 0.0176(4) Uani 1 1 d . . . . .
H8 H 0.2865 0.1644 0.6280 0.021 Uiso 1 1 calc R . . . .
C9 C 0.4021(2) 0.27135(15) 0.62400(15) 0.0155(4) Uani 1 1 d . . . . .
C10 C 0.2734(2) 0.41033(17) 0.92062(16) 0.0229(5) Uani 1 1 d . . . . .
H10A H 0.2519 0.4627 0.8851 0.034 Uiso 1 1 calc GR . . . .
H10B H 0.3585 0.4111 0.9323 0.034 Uiso 1 1 calc GR . . . .
H10C H 0.2304 0.4117 0.9771 0.034 Uiso 1 1 calc GR . . . .
C11 C 0.4059(2) 0.33315(14) 0.39436(15) 0.0152(4) Uani 1 1 d . . . . .
C12 C 0.2873(2) 0.30294(15) 0.39792(15) 0.0192(5) Uani 1 1 d . . . . .
H12 H 0.2595 0.2746 0.4503 0.023 Uiso 1 1 calc R . . . .
C13 C 0.2091(2) 0.31410(16) 0.32509(16) 0.0194(5) Uani 1 1 d . . . . .
H13 H 0.1304 0.2926 0.3287 0.023 Uiso 1 1 calc R . . . .
C14 C 0.2494(2) 0.35766(15) 0.24657(15) 0.0171(4) Uani 1 1 d . . . . .
C15 C 0.3692(2) 0.38617(15) 0.24122(16) 0.0185(5) Uani 1 1 d . . . . .
H15 H 0.3974 0.4137 0.1885 0.022 Uiso 1 1 calc R . . . .
C16 C 0.4462(2) 0.37363(15) 0.31418(16) 0.0177(4) Uani 1 1 d . . . . .
H16 H 0.5261 0.3925 0.3097 0.021 Uiso 1 1 calc R . . . .
C17 C 0.0583(2) 0.34162(17) 0.17489(18) 0.0250(5) Uani 1 1 d . . . . .
H17A H 0.0188 0.3554 0.1186 0.037 Uiso 1 1 calc GR . . . .
H17B H 0.0162 0.3708 0.2238 0.037 Uiso 1 1 calc GR . . . .
H17C H 0.0583 0.2768 0.1843 0.037 Uiso 1 1 calc GR . . . .
C18 C 0.4949(2) 0.16713(15) 0.51665(15) 0.0166(4) Uani 1 1 d . . . . .
C19 C 0.5990(3) 0.08043(16) 0.40811(18) 0.0260(5) Uani 1 1 d . . . . .
H19A H 0.6412 0.0871 0.3517 0.039 Uiso 1 1 calc GR . . . .
H19B H 0.5341 0.0377 0.4007 0.039 Uiso 1 1 calc GR . . . .
H19C H 0.6535 0.0585 0.4537 0.039 Uiso 1 1 calc GR . . . .
C20 C 0.7241(2) 0.57133(15) 0.41713(16) 0.0182(5) Uani 1 1 d . . . . .
C21 C 0.6096(2) 0.63255(15) 0.40727(15) 0.0173(4) Uani 1 1 d . . . . .
C22 C 0.8038(2) 0.59617(18) 0.4970(2) 0.0293(6) Uani 1 1 d . . . . .
H22A H 0.7558 0.5990 0.5511 0.044 Uiso 1 1 calc GR . . . .
H22B H 0.8405 0.6544 0.4863 0.044 Uiso 1 1 calc GR . . . .
H22C H 0.8653 0.5507 0.5042 0.044 Uiso 1 1 calc GR . . . .
C23 C 0.7992(2) 0.56079(17) 0.33110(19) 0.0269(5) Uani 1 1 d . . . . .
H23A H 0.8668 0.5218 0.3431 0.040 Uiso 1 1 calc GR . . . .
H23B H 0.8275 0.6195 0.3119 0.040 Uiso 1 1 calc GR . . . .
H23C H 0.7504 0.5344 0.2841 0.040 Uiso 1 1 calc GR . . . .
C24 C 0.6230(2) 0.72860(16) 0.44425(17) 0.0243(5) Uani 1 1 d . . . . .
H24A H 0.5484 0.7609 0.4369 0.036 Uiso 1 1 calc GR . . . .
H24B H 0.6857 0.7597 0.4118 0.036 Uiso 1 1 calc GR . . . .
H24C H 0.6434 0.7259 0.5074 0.036 Uiso 1 1 calc GR . . . .
C25 C 0.5573(2) 0.63461(17) 0.31171(16) 0.0217(5) Uani 1 1 d . . . . .
H25A H 0.5480 0.5734 0.2898 0.033 Uiso 1 1 calc GR . . . .
H25B H 0.6109 0.6675 0.2724 0.033 Uiso 1 1 calc GR . . . .
H25C H 0.4802 0.6643 0.3127 0.033 Uiso 1 1 calc GR . . . .
B1 B 0.5599(2) 0.49737(17) 0.47366(17) 0.0155(5) Uani 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 C6 1.364(3) . ?
O1 C10 1.432(3) . ?
O2 C14 1.367(3) . ?
O2 C17 1.427(3) . ?
O3 C18 1.353(3) . ?
O3 C19 1.432(3) . ?
O4 C18 1.212(3) . ?
O5 C20 1.474(3) . ?
O5 B1 1.368(3) . ?
O6 C21 1.464(3) . ?
O6 B1 1.361(3) . ?
N1 C1 1.486(3) . ?
N1 C9 1.434(3) . ?
N1 C18 1.371(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.538(3) . ?
C1 C11 1.516(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.546(3) . ?
C2 B1 1.580(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.502(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.402(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.389(3) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(3) . ?
C14 C15 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.562(3) . ?
C20 C22 1.517(4) . ?
C20 C23 1.526(3) . ?
C21 C24 1.518(3) . ?
C21 C25 1.524(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C6 O1 C10 117.27(19) . . ?
C14 O2 C17 116.83(18) . . ?
C18 O3 C19 114.87(18) . . ?
B1 O5 C20 106.49(17) . . ?
B1 O6 C21 107.47(17) . . ?
C9 N1 C1 120.31(17) . . ?
C18 N1 C1 119.47(18) . . ?
C18 N1 C9 120.05(18) . . ?
N1 C1 H1 107.8 . . ?
N1 C1 C2 111.45(17) . . ?
N1 C1 C11 112.41(18) . . ?
C2 C1 H1 107.8 . . ?
C11 C1 H1 107.8 . . ?
C11 C1 C2 109.46(17) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C3 109.54(17) . . ?
C1 C2 B1 111.34(18) . . ?
C3 C2 H2 108.2 . . ?
C3 C2 B1 111.30(18) . . ?
B1 C2 H2 108.2 . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 C2 106.50(17) . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
C5 C4 C3 122.77(19) . . ?
C5 C4 C9 119.8(2) . . ?
C9 C4 C3 117.2(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
O1 C6 C5 124.8(2) . . ?
O1 C6 C7 115.5(2) . . ?
C5 C6 C7 119.7(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 N1 116.7(2) . . ?
C8 C9 N1 122.94(19) . . ?
C8 C9 C4 120.3(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C1 122.2(2) . . ?
C12 C11 C16 118.1(2) . . ?
C16 C11 C1 119.5(2) . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
O2 C14 C13 124.5(2) . . ?
O2 C14 C15 116.2(2) . . ?
C15 C14 C13 119.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 N1 110.12(18) . . ?
O4 C18 O3 123.9(2) . . ?
O4 C18 N1 126.0(2) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 C21 102.49(17) . . ?
O5 C20 C22 106.01(18) . . ?
O5 C20 C23 107.56(18) . . ?
C22 C20 C21 114.1(2) . . ?
C22 C20 C23 110.6(2) . . ?
C23 C20 C21 115.1(2) . . ?
O6 C21 C20 102.41(16) . . ?
O6 C21 C24 107.48(18) . . ?
O6 C21 C25 106.67(19) . . ?
C24 C21 C20 114.9(2) . . ?
C24 C21 C25 110.55(19) . . ?
C25 C21 C20 114.00(19) . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 B1 C2 123.4(2) . . ?
O6 B1 O5 114.0(2) . . ?
O6 B1 C2 122.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C7 C8 179.5(2) . . . . ?
O2 C14 C15 C16 179.1(2) . . . . ?
O5 C20 C21 O6 26.1(2) . . . . ?
O5 C20 C21 C24 142.27(19) . . . . ?
O5 C20 C21 C25 -88.7(2) . . . . ?
N1 C1 C2 C3 34.9(2) . . . . ?
N1 C1 C2 B1 158.44(18) . . . . ?
N1 C1 C11 C12 30.5(3) . . . . ?
N1 C1 C11 C16 -154.5(2) . . . . ?
C1 N1 C9 C4 -38.0(3) . . . . ?
C1 N1 C9 C8 140.8(2) . . . . ?
C1 N1 C18 O3 -1.8(3) . . . . ?
C1 N1 C18 O4 177.4(2) . . . . ?
C1 C2 C3 C4 -65.1(2) . . . . ?
C1 C2 B1 O5 -44.0(3) . . . . ?
C1 C2 B1 O6 139.6(2) . . . . ?
C1 C11 C12 C13 173.6(2) . . . . ?
C1 C11 C16 C15 -173.0(2) . . . . ?
C2 C1 C11 C12 -93.9(2) . . . . ?
C2 C1 C11 C16 81.1(2) . . . . ?
C2 C3 C4 C5 -129.0(2) . . . . ?
C2 C3 C4 C9 46.2(3) . . . . ?
C3 C2 B1 O5 78.5(3) . . . . ?
C3 C2 B1 O6 -97.8(3) . . . . ?
C3 C4 C5 C6 176.8(2) . . . . ?
C3 C4 C9 N1 3.5(3) . . . . ?
C3 C4 C9 C8 -175.3(2) . . . . ?
C4 C5 C6 O1 178.5(2) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C5 C4 C9 N1 178.84(19) . . . . ?
C5 C4 C9 C8 0.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 2.3(3) . . . . ?
C7 C8 C9 N1 179.2(2) . . . . ?
C7 C8 C9 C4 -2.1(3) . . . . ?
C9 N1 C1 C2 16.1(3) . . . . ?
C9 N1 C1 C11 -107.2(2) . . . . ?
C9 N1 C18 O3 -177.17(18) . . . . ?
C9 N1 C18 O4 2.0(4) . . . . ?
C9 C4 C5 C6 1.8(3) . . . . ?
C10 O1 C6 C5 2.3(3) . . . . ?
C10 O1 C6 C7 -177.7(2) . . . . ?
C11 C1 C2 C3 159.88(18) . . . . ?
C11 C1 C2 B1 -76.6(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C11 C16 C15 2.1(3) . . . . ?
C12 C13 C14 O2 -178.5(2) . . . . ?
C12 C13 C14 C15 2.5(3) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C16 C11 C12 C13 -1.5(3) . . . . ?
C17 O2 C14 C13 -1.6(3) . . . . ?
C17 O2 C14 C15 177.4(2) . . . . ?
C18 N1 C1 C2 -159.28(19) . . . . ?
C18 N1 C1 C11 77.4(3) . . . . ?
C18 N1 C9 C4 137.4(2) . . . . ?
C18 N1 C9 C8 -43.9(3) . . . . ?
C19 O3 C18 O4 -2.7(3) . . . . ?
C19 O3 C18 N1 176.5(2) . . . . ?
C20 O5 B1 O6 10.6(3) . . . . ?
C20 O5 B1 C2 -166.0(2) . . . . ?
C21 O6 B1 O5 7.5(3) . . . . ?
C21 O6 B1 C2 -175.9(2) . . . . ?
C22 C20 C21 O6 -88.0(2) . . . . ?
C22 C20 C21 C24 28.2(3) . . . . ?
C22 C20 C21 C25 157.2(2) . . . . ?
C23 C20 C21 O6 142.53(19) . . . . ?
C23 C20 C21 C24 -101.3(2) . . . . ?
C23 C20 C21 C25 27.7(3) . . . . ?
B1 O5 C20 C21 -22.6(2) . . . . ?
B1 O5 C20 C22 97.3(2) . . . . ?
B1 O5 C20 C23 -144.3(2) . . . . ?
B1 O6 C21 C20 -20.9(2) . . . . ?
B1 O6 C21 C24 -142.3(2) . . . . ?
B1 O6 C21 C25 99.1(2) . . . . ?
B1 C2 C3 C4 171.38(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.598
