# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_a16027_a
_database_code_depnum_ccdc_archive 'CCDC 2026556'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;Caltech XRCF
United States of America
;
_audit_update_record             
;
2020-09-01 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2016-02-17
_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         'C18 H19 N O6'
_chemical_formula_sum            'C18 H19 N O6'
_chemical_formula_weight         345.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4539(6)
_cell_length_b                   9.8703(7)
_cell_length_c                   10.6887(7)
_cell_angle_alpha                114.437(3)
_cell_angle_beta                 105.326(3)
_cell_angle_gamma                102.469(3)
_cell_volume                     813.45(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.44
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0641 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9575.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            65383
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         37.744
_diffrn_reflns_theta_min         2.281
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7376
_reflns_number_total             8412
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         8412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.043
_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)+(0.0591P)²+0.1262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1046
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.68727(7) 0.52373(6) 0.09930(5) 0.02314(9) Uani 1 1 d . . . . .
O2 O 0.40785(6) 0.73420(6) 0.48490(5) 0.02132(9) Uani 1 1 d . . . . .
O3 O 0.15129(5) 0.44500(5) 0.08371(5) 0.02076(9) Uani 1 1 d . . . . .
H3 H 0.2000 0.4558 0.0310 0.031 Uiso 1 1 calc GR . . . .
O4 O 0.61976(4) 0.81947(5) 0.26235(4) 0.01220(7) Uani 1 1 d . . . . .
O5 O 1.00681(5) 0.84698(6) 0.33568(5) 0.02028(8) Uani 1 1 d . . . . .
O6 O 0.57802(5) 0.41278(5) 0.21366(5) 0.01747(8) Uani 1 1 d . . . . .
N1 N 0.76718(5) 0.82426(5) 0.34353(5) 0.01319(7) Uani 1 1 d . . . . .
C1 C 0.66779(6) 0.53288(6) 0.20924(6) 0.01449(8) Uani 1 1 d . . . . .
C2 C 0.74695(6) 0.68559(6) 0.36298(6) 0.01394(8) Uani 1 1 d . . . . .
H2 H 0.8535 0.6899 0.4164 0.017 Uiso 1 1 calc R . . . .
C3 C 0.65419(7) 0.69824(7) 0.46273(6) 0.01665(9) Uani 1 1 d . . . . .
H3A H 0.6262 0.5987 0.4680 0.020 Uiso 1 1 calc R . . . .
H3B H 0.7208 0.7887 0.5655 0.020 Uiso 1 1 calc R . . . .
C4 C 0.50587(6) 0.72411(6) 0.40090(6) 0.01450(8) Uani 1 1 d . . . . .
C5 C 0.34829(7) 0.59995(7) 0.33392(6) 0.01668(9) Uani 1 1 d . . . . .
H5 H 0.3460 0.4949 0.3261 0.020 Uiso 1 1 calc R . . . .
C6 C 0.20825(6) 0.59298(7) 0.22050(7) 0.01753(9) Uani 1 1 d . . . . .
H6 H 0.1229 0.5920 0.2593 0.021 Uiso 1 1 calc R . . . .
C7 C 0.24107(6) 0.73538(7) 0.19836(7) 0.01824(9) Uani 1 1 d . . . . .
H7 H 0.1553 0.7434 0.1352 0.022 Uiso 1 1 calc R . . . .
C8 C 0.38270(6) 0.85145(6) 0.26139(7) 0.01685(9) Uani 1 1 d . . . . .
H8 H 0.3900 0.9397 0.2448 0.020 Uiso 1 1 calc R . . . .
C9 C 0.53061(6) 0.85160(6) 0.35636(6) 0.01389(8) Uani 1 1 d . . . . .
H9 H 0.5908 0.9597 0.4480 0.017 Uiso 1 1 calc R . . . .
C10 C 0.89461(6) 0.89027(6) 0.32003(6) 0.01385(8) Uani 1 1 d . . . . .
C11 C 0.89564(6) 1.02448(6) 0.28853(6) 0.01455(8) Uani 1 1 d . . . . .
C12 C 0.97786(7) 1.04492(8) 0.20252(7) 0.02005(10) Uani 1 1 d . . . . .
H12 H 1.0252 0.9711 0.1616 0.024 Uiso 1 1 calc R . . . .
C13 C 0.99048(8) 1.17345(9) 0.17672(8) 0.02574(13) Uani 1 1 d . . . . .
H13 H 1.0453 1.1866 0.1172 0.031 Uiso 1 1 calc R . . . .
C14 C 0.92292(8) 1.28232(9) 0.23804(9) 0.02665(13) Uani 1 1 d . . . . .
H14 H 0.9304 1.3692 0.2194 0.032 Uiso 1 1 calc R . . . .
C15 C 0.84409(7) 1.26451(8) 0.32697(8) 0.02255(11) Uani 1 1 d . . . . .
H15 H 0.8003 1.3407 0.3708 0.027 Uiso 1 1 calc R . . . .
C16 C 0.82953(6) 1.13519(7) 0.35165(7) 0.01661(9) Uani 1 1 d . . . . .
H16 H 0.7748 1.1224 0.4113 0.020 Uiso 1 1 calc R . . . .
C17 C 0.49494(8) 0.26132(7) 0.07248(7) 0.02213(11) Uani 1 1 d . . . . .
H17A H 0.5707 0.2261 0.0308 0.027 Uiso 1 1 calc R . . . .
H17B H 0.4178 0.2734 -0.0014 0.027 Uiso 1 1 calc R . . . .
C18 C 0.41159(8) 0.14145(8) 0.10639(8) 0.02654(13) Uani 1 1 d . . . . .
H18A H 0.3545 0.0373 0.0142 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.3366 0.1775 0.1470 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.4892 0.1313 0.1801 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2069(7) . ?
O2 C4 1.4424(7) . ?
O2 C5 1.4510(7) . ?
O3 H3 0.8400 . ?
O3 C6 1.4277(8) . ?
O4 N1 1.4127(6) . ?
O4 C9 1.4561(6) . ?
O5 C10 1.2234(7) . ?
O6 C1 1.3270(7) . ?
O6 C17 1.4591(7) . ?
N1 C2 1.4480(7) . ?
N1 C10 1.3767(7) . ?
C1 C2 1.5316(7) . ?
C2 H2 1.0000 . ?
C2 C3 1.5339(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5075(8) . ?
C4 C5 1.4682(8) . ?
C4 C9 1.5140(8) . ?
C5 H5 1.0000 . ?
C5 C6 1.5068(9) . ?
C6 H6 1.0000 . ?
C6 C7 1.5011(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.3347(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.4944(8) . ?
C9 H9 1.0000 . ?
C10 C11 1.4945(8) . ?
C11 C12 1.3977(8) . ?
C11 C16 1.3956(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.3932(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.3882(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.3950(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.3928(8) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5017(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C5 60.99(3) . . ?
C6 O3 H3 109.5 . . ?
N1 O4 C9 109.45(4) . . ?
C1 O6 C17 116.14(5) . . ?
O4 N1 C2 110.53(4) . . ?
C10 N1 O4 116.60(4) . . ?
C10 N1 C2 122.41(4) . . ?
O1 C1 O6 124.83(5) . . ?
O1 C1 C2 123.79(5) . . ?
O6 C1 C2 111.38(4) . . ?
N1 C2 C1 109.45(4) . . ?
N1 C2 H2 108.5 . . ?
N1 C2 C3 107.27(4) . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 114.37(4) . . ?
C3 C2 H2 108.5 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.42(4) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
O2 C4 C3 114.92(4) . . ?
O2 C4 C5 59.80(4) . . ?
O2 C4 C9 114.11(5) . . ?
C3 C4 C9 114.18(4) . . ?
C5 C4 C3 122.07(5) . . ?
C5 C4 C9 119.51(5) . . ?
O2 C5 C4 59.22(3) . . ?
O2 C5 H5 115.7 . . ?
O2 C5 C6 115.76(5) . . ?
C4 C5 H5 115.7 . . ?
C4 C5 C6 122.52(5) . . ?
C6 C5 H5 115.7 . . ?
O3 C6 C5 109.05(5) . . ?
O3 C6 H6 107.2 . . ?
O3 C6 C7 112.48(5) . . ?
C5 C6 H6 107.2 . . ?
C7 C6 C5 113.46(5) . . ?
C7 C6 H6 107.2 . . ?
C6 C7 H7 117.8 . . ?
C8 C7 C6 124.41(5) . . ?
C8 C7 H7 117.8 . . ?
C7 C8 H8 117.9 . . ?
C7 C8 C9 124.22(5) . . ?
C9 C8 H8 117.9 . . ?
O4 C9 C4 108.30(4) . . ?
O4 C9 C8 104.16(4) . . ?
O4 C9 H9 109.8 . . ?
C4 C9 H9 109.8 . . ?
C8 C9 C4 114.81(4) . . ?
C8 C9 H9 109.8 . . ?
O5 C10 N1 120.20(5) . . ?
O5 C10 C11 122.11(5) . . ?
N1 C10 C11 117.49(4) . . ?
C12 C11 C10 117.52(5) . . ?
C16 C11 C10 122.35(5) . . ?
C16 C11 C12 119.92(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.05(6) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.93(6) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.18(6) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(6) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.79(5) . . ?
C15 C16 H16 120.1 . . ?
O6 C17 H17A 110.4 . . ?
O6 C17 H17B 110.4 . . ?
O6 C17 C18 106.77(5) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C1 C2 N1 32.43(7) . . . . ?
O1 C1 C2 C3 152.80(6) . . . . ?
O2 C4 C5 C6 102.72(6) . . . . ?
O2 C4 C9 O4 -175.31(4) . . . . ?
O2 C4 C9 C8 -59.41(6) . . . . ?
O2 C5 C6 O3 -172.59(4) . . . . ?
O2 C5 C6 C7 61.20(6) . . . . ?
O3 C6 C7 C8 -118.76(6) . . . . ?
O4 N1 C2 C1 59.09(5) . . . . ?
O4 N1 C2 C3 -65.52(5) . . . . ?
O4 N1 C10 O5 -151.78(5) . . . . ?
O4 N1 C10 C11 33.40(6) . . . . ?
O5 C10 C11 C12 33.04(8) . . . . ?
O5 C10 C11 C16 -141.58(6) . . . . ?
O6 C1 C2 N1 -148.56(4) . . . . ?
O6 C1 C2 C3 -28.19(6) . . . . ?
N1 O4 C9 C4 -60.15(5) . . . . ?
N1 O4 C9 C8 177.21(4) . . . . ?
N1 C2 C3 C4 52.05(5) . . . . ?
N1 C10 C11 C12 -152.25(5) . . . . ?
N1 C10 C11 C16 33.14(7) . . . . ?
C1 O6 C17 C18 175.96(5) . . . . ?
C1 C2 C3 C4 -69.52(6) . . . . ?
C2 N1 C10 O5 -10.28(8) . . . . ?
C2 N1 C10 C11 174.90(4) . . . . ?
C2 C3 C4 O2 178.71(4) . . . . ?
C2 C3 C4 C5 110.02(5) . . . . ?
C2 C3 C4 C9 -46.69(6) . . . . ?
C3 C4 C5 O2 102.16(5) . . . . ?
C3 C4 C5 C6 -155.13(5) . . . . ?
C3 C4 C9 O4 49.71(6) . . . . ?
C3 C4 C9 C8 165.61(4) . . . . ?
C4 O2 C5 C6 -114.03(5) . . . . ?
C4 C5 C6 O3 118.90(5) . . . . ?
C4 C5 C6 C7 -7.31(8) . . . . ?
C5 O2 C4 C3 -114.02(5) . . . . ?
C5 O2 C4 C9 111.34(5) . . . . ?
C5 C4 C9 O4 -107.64(5) . . . . ?
C5 C4 C9 C8 8.26(7) . . . . ?
C5 C6 C7 C8 5.62(8) . . . . ?
C6 C7 C8 C9 3.49(9) . . . . ?
C7 C8 C9 O4 107.72(6) . . . . ?
C7 C8 C9 C4 -10.54(8) . . . . ?
C9 O4 N1 C2 71.68(5) . . . . ?
C9 O4 N1 C10 -142.45(4) . . . . ?
C9 C4 C5 O2 -102.33(5) . . . . ?
C9 C4 C5 C6 0.39(8) . . . . ?
C10 N1 C2 C1 -84.44(6) . . . . ?
C10 N1 C2 C3 150.94(5) . . . . ?
C10 C11 C12 C13 -176.34(5) . . . . ?
C10 C11 C16 C15 175.33(5) . . . . ?
C11 C12 C13 C14 0.77(9) . . . . ?
C12 C11 C16 C15 0.83(8) . . . . ?
C12 C13 C14 C15 0.80(10) . . . . ?
C13 C14 C15 C16 -1.55(10) . . . . ?
C14 C15 C16 C11 0.73(9) . . . . ?
C16 C11 C12 C13 -1.59(8) . . . . ?
C17 O6 C1 O1 -1.75(8) . . . . ?
C17 O6 C1 C2 179.25(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p16469_b
_database_code_depnum_ccdc_archive 'CCDC 2026557'
loop_
_audit_author_name
_audit_author_address
'Michael K. Takase'
;Caltech XRCF
United States of America
;
_audit_update_record             
;
2020-09-01 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Br N O4'
_chemical_formula_sum            'C14 H14 Br N O4'
_chemical_formula_weight         340.17
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6346(7)
_cell_length_b                   5.6380(5)
_cell_length_c                   15.6510(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.728(3)
_cell_angle_gamma                90
_cell_volume                     740.15(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      43.35
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.566
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0973 before and 0.0777 after correction.
The Ratio of minimum to maximum transmission is 0.8261.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            68030
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         45.369
_diffrn_reflns_theta_min         2.428
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                10919
_reflns_number_total             12256
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 4468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0322(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         12256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      0.989
_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)+(0.0177P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0541
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
2.f :
 C5(H5)
;
_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
Br1 Br 0.15673(2) 0.20544(3) 0.66433(2) 0.02070(3) Uani 1 1 d . . . . .
O1 O 0.86808(9) 0.26712(16) 0.92479(6) 0.01991(14) Uani 1 1 d . . . . .
O2 O 0.80569(9) 0.56641(15) 0.82777(6) 0.01865(13) Uani 1 1 d . . . . .
O3 O 0.54192(7) 0.19604(14) 0.73103(4) 0.01256(9) Uani 1 1 d . . . . .
H3 H 0.4920 0.0738 0.7396 0.019 Uiso 1 1 calc GR . . . .
O4 O 0.43360(9) 0.76829(12) 0.77810(5) 0.01514(11) Uani 1 1 d . . . . .
N1 N 0.50418(9) 0.38290(13) 0.78093(5) 0.00968(10) Uani 1 1 d . . . . .
C1 C 0.77148(10) 0.39468(16) 0.87841(6) 0.01261(12) Uani 1 1 d . . . . .
C2 C 0.59223(10) 0.38553(15) 0.87231(5) 0.00991(11) Uani 1 1 d . . . . .
H2 H 0.5623 0.5331 0.9000 0.012 Uiso 1 1 calc R . . . .
C3 C 0.55204(9) 0.17365(15) 0.92407(5) 0.01207(13) Uani 1 1 d . . . . .
H3A H 0.5754 0.0250 0.8959 0.014 Uiso 1 1 calc R . . . .
H3B H 0.6205 0.1778 0.9845 0.014 Uiso 1 1 calc R . . . .
C4 C 0.38480(10) 0.17397(16) 0.92825(6) 0.01385(14) Uani 1 1 d . . . . .
C5 C 0.24845(11) 0.1758(2) 0.93395(7) 0.01919(18) Uani 1 1 d . . . . .
H5 H 0.1407 0.1773 0.9384 0.023 Uiso 1 1 calc R . . . .
C6 C 0.43888(10) 0.58063(14) 0.73832(5) 0.00977(11) Uani 1 1 d . . . . .
C7 C 0.37367(10) 0.56879(15) 0.64074(5) 0.01081(11) Uani 1 1 d . . . . .
C8 C 0.25012(11) 0.42021(17) 0.59858(6) 0.01398(13) Uani 1 1 d . . . . .
C9 C 0.18903(13) 0.4296(2) 0.50811(7) 0.01944(17) Uani 1 1 d . . . . .
H9 H 0.1047 0.3270 0.4805 0.023 Uiso 1 1 calc R . . . .
C10 C 0.25266(13) 0.5909(2) 0.45849(6) 0.01998(17) Uani 1 1 d . . . . .
H10 H 0.2126 0.5970 0.3965 0.024 Uiso 1 1 calc R . . . .
C11 C 0.37425(13) 0.74265(18) 0.49900(6) 0.01878(17) Uani 1 1 d . . . . .
H11 H 0.4172 0.8527 0.4649 0.023 Uiso 1 1 calc R . . . .
C12 C 0.43332(11) 0.73350(17) 0.58986(6) 0.01521(14) Uani 1 1 d . . . . .
H12 H 0.5150 0.8403 0.6176 0.018 Uiso 1 1 calc R . . . .
C13 C 0.97467(13) 0.6010(2) 0.83269(8) 0.0222(2) Uani 1 1 d . . . . .
H13A H 1.0230 0.4521 0.8178 0.027 Uiso 1 1 calc R . . . .
H13B H 1.0310 0.6494 0.8928 0.027 Uiso 1 1 calc R . . . .
C14 C 0.98734(16) 0.7926(3) 0.76768(11) 0.0312(3) Uani 1 1 d . . . . .
H14A H 0.9352 0.7397 0.7082 0.047 Uiso 1 1 calc GR . . . .
H14B H 1.1000 0.8259 0.7709 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.9351 0.9369 0.7817 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.8892(9) . ?
O1 C1 1.2052(12) . ?
O2 C1 1.3282(11) . ?
O2 C13 1.4559(13) . ?
O3 H3 0.8400 . ?
O3 N1 1.3953(10) . ?
O4 C6 1.2340(11) . ?
N1 C2 1.4518(11) . ?
N1 C6 1.3517(11) . ?
C1 C2 1.5288(12) . ?
C2 H2 1.0000 . ?
C2 C3 1.5287(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.4610(11) . ?
C4 C5 1.2017(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.4986(11) . ?
C7 C8 1.3932(13) . ?
C7 C12 1.3987(12) . ?
C8 C9 1.3899(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3905(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3858(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3931(13) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5054(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C13 115.36(8) . . ?
N1 O3 H3 109.5 . . ?
O3 N1 C2 114.95(6) . . ?
C6 N1 O3 118.17(7) . . ?
C6 N1 C2 122.50(7) . . ?
O1 C1 O2 125.05(9) . . ?
O1 C1 C2 124.28(8) . . ?
O2 C1 C2 110.65(8) . . ?
N1 C2 C1 110.34(7) . . ?
N1 C2 H2 107.8 . . ?
N1 C2 C3 112.48(7) . . ?
C1 C2 H2 107.8 . . ?
C3 C2 C1 110.31(7) . . ?
C3 C2 H2 107.8 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.95(7) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C5 C4 C3 178.30(10) . . ?
C4 C5 H5 180.0 . . ?
O4 C6 N1 121.28(8) . . ?
O4 C6 C7 120.17(8) . . ?
N1 C6 C7 118.55(7) . . ?
C8 C7 C6 124.73(7) . . ?
C8 C7 C12 118.27(8) . . ?
C12 C7 C6 116.78(8) . . ?
C7 C8 Br1 120.35(6) . . ?
C9 C8 Br1 118.14(7) . . ?
C9 C8 C7 121.49(9) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.29(10) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.33(9) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.88(9) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.70(9) . . ?
C11 C12 H12 119.6 . . ?
O2 C13 H13A 110.3 . . ?
O2 C13 H13B 110.3 . . ?
O2 C13 C14 107.04(9) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/CHCl3'
