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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pyd-138
_database_code_depnum_ccdc_archive 'CCDC 1835168'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_audit_creation_date             2018-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        PYD-138
_chemical_formula_moiety         'C18 H21 B Br N O4'
_chemical_formula_sum            'C18 H21 B Br N O4'
_chemical_formula_weight         406.08
_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'
B B 0.0013 0.0007 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9737(3)
_cell_length_b                   23.8115(9)
_cell_length_c                   11.0278(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.529(4)
_cell_angle_gamma                90
_cell_volume                     1810.96(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6219
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.6250
_cell_measurement_theta_min      3.0410
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.657
_exptl_absorpt_coefficient_mu    2.292
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15590
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.935
_diffrn_reflns_theta_min         3.075
_diffrn_ambient_temperature      123
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00   6.00   0.50   17.15    --    5.00  38.00   9.00   50
  2  ω    -34.00  64.00   0.50   17.15    --   -7.20  38.00   9.00  196
  3  ω    -97.00  82.00   0.50   17.15    --   -7.20  29.00  90.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1022868000
_diffrn_orient_matrix_UB_12      -0.0029466000
_diffrn_orient_matrix_UB_13      0.0081846000
_diffrn_orient_matrix_UB_21      0.0043874000
_diffrn_orient_matrix_UB_22      0.0180846000
_diffrn_orient_matrix_UB_23      -0.0506762000
_diffrn_orient_matrix_UB_31      0.0095392000
_diffrn_orient_matrix_UB_32      0.0234740000
_diffrn_orient_matrix_UB_33      0.0400055000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3390
_reflns_number_total             4117
_reflns_odcompleteness_completeness 98.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.019
_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)+(0.0277P)²+0.9678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0655
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00J(H00E,H00F,H00H), C00M(H00J,H00M,H00N), C00N(H00O,H00P,H00Q), C00P(H00R,
 H00S,H00T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.58773(3) 0.40356(2) -0.03969(2) 0.02403(7) Uani 1 1 d . . . . .
O002 O 0.79514(18) 0.30123(5) 0.12732(12) 0.0206(3) Uani 1 1 d . . . . .
O003 O 0.1195(2) 0.55787(6) 0.20618(13) 0.0281(3) Uani 1 1 d . . . . .
O004 O 0.54437(18) 0.28066(5) 0.23181(13) 0.0236(3) Uani 1 1 d . . . . .
O005 O 0.1426(2) 0.38728(6) 0.39659(14) 0.0285(3) Uani 1 1 d . . . . .
N006 N 0.1248(2) 0.46580(6) 0.27216(15) 0.0174(3) Uani 1 1 d . . . . .
C007 C 0.3212(3) 0.37933(8) 0.12238(17) 0.0193(4) Uani 1 1 d . . . . .
H007 H 0.280874 0.357923 0.186784 0.023 Uiso 1 1 calc R . . . .
C008 C 0.4881(3) 0.36388(8) 0.08877(17) 0.0186(4) Uani 1 1 d . . . . .
C009 C 0.1529(3) 0.52355(8) 0.28751(18) 0.0196(4) Uani 1 1 d . . . . .
C00A C 0.1632(3) 0.43703(8) 0.38403(18) 0.0194(4) Uani 1 1 d . . . . .
C00B C 0.0392(3) 0.44047(8) 0.15640(18) 0.0213(4) Uani 1 1 d . . . . .
H00A H -0.056880 0.466865 0.112683 0.026 Uiso 1 1 calc R . . . .
H00B H -0.030862 0.405921 0.173818 0.026 Uiso 1 1 calc R . . . .
C00C C 0.2253(3) 0.53242(8) 0.41983(18) 0.0194(4) Uani 1 1 d . . . . .
C00D C 0.2300(3) 0.48074(8) 0.47803(18) 0.0203(4) Uani 1 1 d . . . . .
C00E C 0.1873(3) 0.42572(8) 0.07318(18) 0.0218(4) Uani 1 1 d . . . . .
H00C H 0.118003 0.414515 -0.008113 0.026 Uiso 1 1 calc R . . . .
H00D H 0.265029 0.459559 0.061505 0.026 Uiso 1 1 calc R . . . .
C00F C 0.7047(3) 0.24425(8) 0.28553(19) 0.0220(4) Uani 1 1 d . . . . .
C00G C 0.2795(3) 0.58116(9) 0.4827(2) 0.0273(5) Uani 1 1 d . . . . .
H00G H 0.275033 0.616447 0.442178 0.033 Uiso 1 1 calc R . . . .
C00H C 0.8468(3) 0.24718(8) 0.18873(18) 0.0197(4) Uani 1 1 d . . . . .
C00I C 0.2885(3) 0.47590(9) 0.60288(19) 0.0268(5) Uani 1 1 d . . . . .
H00I H 0.290555 0.440625 0.643272 0.032 Uiso 1 1 calc R . . . .
C00J C 1.0591(3) 0.24850(9) 0.2414(2) 0.0260(4) Uani 1 1 d . . . . .
H00E H 1.137060 0.250681 0.174572 0.039 Uiso 1 1 calc GR . . . .
H00F H 1.092841 0.214273 0.289229 0.039 Uiso 1 1 calc GR . . . .
H00H H 1.085439 0.281387 0.294716 0.039 Uiso 1 1 calc GR . . . .
C00K C 0.3447(3) 0.52533(10) 0.6671(2) 0.0321(5) Uani 1 1 d . . . . .
H00K H 0.386332 0.523624 0.753076 0.039 Uiso 1 1 calc R . . . .
C00L C 0.3409(3) 0.57656(10) 0.6080(2) 0.0325(5) Uani 1 1 d . . . . .
H00L H 0.381088 0.609322 0.654033 0.039 Uiso 1 1 calc R . . . .
C00M C 0.7892(3) 0.27017(9) 0.40746(19) 0.0310(5) Uani 1 1 d . . . . .
H00J H 0.845823 0.306815 0.393253 0.046 Uiso 1 1 calc GR . . . .
H00M H 0.889999 0.245432 0.449636 0.046 Uiso 1 1 calc GR . . . .
H00N H 0.686366 0.274991 0.458255 0.046 Uiso 1 1 calc GR . . . .
C00N C 0.6216(3) 0.18669(9) 0.3045(3) 0.0378(6) Uani 1 1 d . . . . .
H00O H 0.536832 0.188890 0.367732 0.057 Uiso 1 1 calc GR . . . .
H00P H 0.727540 0.160308 0.330608 0.057 Uiso 1 1 calc GR . . . .
H00Q H 0.546596 0.173625 0.227455 0.057 Uiso 1 1 calc GR . . . .
B00O B 0.6137(3) 0.31440(9) 0.1487(2) 0.0178(4) Uani 1 1 d . . . . .
C00P C 0.8093(3) 0.20258(9) 0.0897(2) 0.0345(5) Uani 1 1 d . . . . .
H00R H 0.670350 0.201282 0.058117 0.052 Uiso 1 1 calc GR . . . .
H00S H 0.851355 0.165915 0.124225 0.052 Uiso 1 1 calc GR . . . .
H00T H 0.881833 0.211745 0.022663 0.052 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
Br01 C008 1.9168(18) . ?
O002 C00H 1.474(2) . ?
O002 B00O 1.357(2) . ?
O003 C009 1.210(2) . ?
O004 C00F 1.468(2) . ?
O004 B00O 1.361(2) . ?
O005 C00A 1.204(2) . ?
N006 C009 1.396(2) . ?
N006 C00A 1.402(2) . ?
N006 C00B 1.457(2) . ?
C007 H007 0.9500 . ?
C007 C008 1.325(3) . ?
C007 C00E 1.495(3) . ?
C008 B00O 1.556(3) . ?
C009 C00C 1.487(3) . ?
C00A C00D 1.494(3) . ?
C00B H00A 0.9900 . ?
C00B H00B 0.9900 . ?
C00B C00E 1.521(3) . ?
C00C C00D 1.386(3) . ?
C00C C00G 1.376(3) . ?
C00D C00I 1.382(3) . ?
C00E H00C 0.9900 . ?
C00E H00D 0.9900 . ?
C00F C00H 1.562(3) . ?
C00F C00M 1.517(3) . ?
C00F C00N 1.515(3) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.389(3) . ?
C00H C00J 1.508(3) . ?
C00H C00P 1.518(3) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.399(3) . ?
C00J H00E 0.9800 . ?
C00J H00F 0.9800 . ?
C00J H00H 0.9800 . ?
C00K H00K 0.9500 . ?
C00K C00L 1.381(3) . ?
C00L H00L 0.9500 . ?
C00M H00J 0.9800 . ?
C00M H00M 0.9800 . ?
C00M H00N 0.9800 . ?
C00N H00O 0.9800 . ?
C00N H00P 0.9800 . ?
C00N H00Q 0.9800 . ?
C00P H00R 0.9800 . ?
C00P H00S 0.9800 . ?
C00P H00T 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
B00O O002 C00H 107.03(14) . . ?
B00O O004 C00F 107.16(14) . . ?
C009 N006 C00A 111.70(16) . . ?
C009 N006 C00B 123.07(16) . . ?
C00A N006 C00B 124.66(15) . . ?
C008 C007 H007 115.5 . . ?
C008 C007 C00E 129.10(18) . . ?
C00E C007 H007 115.5 . . ?
C007 C008 Br01 119.98(15) . . ?
C007 C008 B00O 123.66(17) . . ?
B00O C008 Br01 116.36(13) . . ?
O003 C009 N006 124.56(19) . . ?
O003 C009 C00C 129.17(18) . . ?
N006 C009 C00C 106.26(16) . . ?
O005 C00A N006 124.87(18) . . ?
O005 C00A C00D 129.50(19) . . ?
N006 C00A C00D 105.63(15) . . ?
N006 C00B H00A 108.9 . . ?
N006 C00B H00B 108.9 . . ?
N006 C00B C00E 113.39(16) . . ?
H00A C00B H00B 107.7 . . ?
C00E C00B H00A 108.9 . . ?
C00E C00B H00B 108.9 . . ?
C00D C00C C009 108.05(16) . . ?
C00G C00C C009 129.97(19) . . ?
C00G C00C C00D 122.0(2) . . ?
C00C C00D C00A 108.28(17) . . ?
C00I C00D C00A 130.47(19) . . ?
C00I C00D C00C 121.25(19) . . ?
C007 C00E C00B 113.27(16) . . ?
C007 C00E H00C 108.9 . . ?
C007 C00E H00D 108.9 . . ?
C00B C00E H00C 108.9 . . ?
C00B C00E H00D 108.9 . . ?
H00C C00E H00D 107.7 . . ?
O004 C00F C00H 102.73(14) . . ?
O004 C00F C00M 106.85(16) . . ?
O004 C00F C00N 107.82(15) . . ?
C00M C00F C00H 112.65(16) . . ?
C00N C00F C00H 115.42(17) . . ?
C00N C00F C00M 110.61(18) . . ?
C00C C00G H00G 121.4 . . ?
C00C C00G C00L 117.1(2) . . ?
C00L C00G H00G 121.4 . . ?
O002 C00H C00F 102.48(13) . . ?
O002 C00H C00J 108.54(15) . . ?
O002 C00H C00P 106.01(16) . . ?
C00J C00H C00F 115.07(17) . . ?
C00J C00H C00P 110.27(16) . . ?
C00P C00H C00F 113.66(16) . . ?
C00D C00I H00I 121.5 . . ?
C00D C00I C00K 117.0(2) . . ?
C00K C00I H00I 121.5 . . ?
C00H C00J H00E 109.5 . . ?
C00H C00J H00F 109.5 . . ?
C00H C00J H00H 109.5 . . ?
H00E C00J H00F 109.5 . . ?
H00E C00J H00H 109.5 . . ?
H00F C00J H00H 109.5 . . ?
C00I C00K H00K 119.4 . . ?
C00L C00K C00I 121.3(2) . . ?
C00L C00K H00K 119.4 . . ?
C00G C00L H00L 119.3 . . ?
C00K C00L C00G 121.4(2) . . ?
C00K C00L H00L 119.3 . . ?
C00F C00M H00J 109.5 . . ?
C00F C00M H00M 109.5 . . ?
C00F C00M H00N 109.5 . . ?
H00J C00M H00M 109.5 . . ?
H00J C00M H00N 109.5 . . ?
H00M C00M H00N 109.5 . . ?
C00F C00N H00O 109.5 . . ?
C00F C00N H00P 109.5 . . ?
C00F C00N H00Q 109.5 . . ?
H00O C00N H00P 109.5 . . ?
H00O C00N H00Q 109.5 . . ?
H00P C00N H00Q 109.5 . . ?
O002 B00O O004 114.45(17) . . ?
O002 B00O C008 125.60(17) . . ?
O004 B00O C008 119.94(17) . . ?
C00H C00P H00R 109.5 . . ?
C00H C00P H00S 109.5 . . ?
C00H C00P H00T 109.5 . . ?
H00R C00P H00S 109.5 . . ?
H00R C00P H00T 109.5 . . ?
H00S C00P H00T 109.5 . . ?

_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 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.702
