# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_mo_140705LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1533667'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H40 B N O4'
_chemical_formula_weight         585.52

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5715(12)
_cell_length_b                   10.6930(9)
_cell_length_c                   21.9043(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.931(2)
_cell_angle_gamma                90
_cell_volume                     3131.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6423
_cell_measurement_theta_min      0.8647
_cell_measurement_theta_max      0.9485

_exptl_crystal_description       Columnar
_exptl_crystal_colour            'Yellow Green'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8647
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            26637
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6423
_reflns_number_gt                4296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.7602P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6423
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.70580(10) 1.11079(12) 0.82776(6) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.93002(10) 0.05701(13) 0.93027(6) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.9408 -0.0038 0.9548 0.044 Uiso 1 1 calc R U . . .
O3 O 0.62966(10) 1.20374(13) 0.89950(6) 0.0300(3) Uani 1 1 d . . . . .
O4 O 1.04433(10) 0.14677(13) 1.00259(6) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.73920(11) 0.78372(14) 0.92272(6) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.74844(19) 1.2036(2) 0.73727(11) 0.0470(7) Uani 1 1 d . . . . .
H20 H 0.8184 1.1786 0.7504 0.071 Uiso 1 1 calc R U . . .
H3 H 0.7456 1.2796 0.7121 0.071 Uiso 1 1 calc R U . . .
H1 H 0.7119 1.1363 0.7128 0.071 Uiso 1 1 calc R U . . .
C2 C 0.70175(15) 1.22841(19) 0.79336(9) 0.0281(5) Uani 1 1 d . . . . .
H19 H 0.7392 1.2945 0.8193 0.034 Uiso 1 1 calc R U . . .
H18 H 0.6316 1.2561 0.7809 0.034 Uiso 1 1 calc R U . . .
C3 C 0.66592(13) 1.11316(19) 0.87912(8) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.67147(13) 0.98803(18) 0.90971(8) 0.0182(4) Uani 1 1 d . . . . .
C5 C 0.73149(13) 0.89474(18) 0.89308(8) 0.0188(4) Uani 1 1 d . . . . .
H17 H 0.7679 0.9087 0.8604 0.023 Uiso 1 1 calc R U . . .
C6 C 0.80419(14) 0.68752(18) 0.90006(8) 0.0211(4) Uani 1 1 d . . . . .
H16 H 0.8718 0.7235 0.9015 0.025 Uiso 1 1 calc R U . . .
H15 H 0.7768 0.6686 0.8562 0.025 Uiso 1 1 calc R U . . .
C7 C 0.81404(14) 0.56691(18) 0.93604(8) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.7476 0.5270 0.9332 0.028 Uiso 1 1 calc R U . . .
H14 H 0.8404 0.5840 0.9803 0.028 Uiso 1 1 calc R U . . .
C8 C 0.88468(15) 0.47965(18) 0.90978(9) 0.0249(5) Uani 1 1 d . . . . .
H11 H 0.8582 0.4644 0.8654 0.030 Uiso 1 1 calc R U . . .
H12 H 0.9507 0.5207 0.9127 0.030 Uiso 1 1 calc R U . . .
C9 C 0.89793(15) 0.35512(18) 0.94366(9) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.8321 0.3136 0.9408 0.030 Uiso 1 1 calc R U . . .
H9 H 0.9247 0.3699 0.9880 0.030 Uiso 1 1 calc R U . . .
C10 C 0.96947(15) 0.26912(19) 0.91615(9) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.9413 0.2502 0.8724 0.034 Uiso 1 1 calc R U . . .
H7 H 1.0346 0.3116 0.9173 0.034 Uiso 1 1 calc R U . . .
C11 C 0.98458(14) 0.15038(18) 0.95248(9) 0.0232(4) Uani 1 1 d . . . . .
C12 C 0.68780(13) 0.76188(18) 0.96915(8) 0.0206(4) Uani 1 1 d . . . . .
H6 H 0.6947 0.6837 0.9901 0.025 Uiso 1 1 calc R U . . .
C13 C 0.62557(14) 0.85160(19) 0.98647(8) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.5886 0.8350 1.0187 0.027 Uiso 1 1 calc R U . . .
C14 C 0.61712(13) 0.96601(18) 0.95679(8) 0.0206(4) Uani 1 1 d . . . . .
H4 H 0.5746 1.0289 0.9685 0.025 Uiso 1 1 calc R U . . .
C15 C 1.02048(14) 0.7524(2) 0.32063(8) 0.0247(5) Uani 1 1 d . . . . .
H21 H 1.0815 0.7420 0.3488 0.030 Uiso 1 1 calc R U . . .
C16 C 0.99409(14) 0.86790(19) 0.29431(8) 0.0232(4) Uani 1 1 d . . . . .
H38 H 1.0369 0.9378 0.3049 0.028 Uiso 1 1 calc R U . . .
C17 C 0.90516(13) 0.88232(18) 0.25240(8) 0.0184(4) Uani 1 1 d . . . . .
H39 H 0.8886 0.9627 0.2352 0.022 Uiso 1 1 calc R U . . .
C18 C 0.83907(13) 0.78286(17) 0.23461(8) 0.0157(4) Uani 1 1 d . . . . .
C19 C 0.65124(12) 0.81536(17) 0.23734(8) 0.0157(4) Uani 1 1 d . . . . .
C20 C 0.59883(13) 0.71425(18) 0.25705(8) 0.0179(4) Uani 1 1 d . . . . .
H27 H 0.6048 0.6343 0.2391 0.021 Uiso 1 1 calc R U . . .
C21 C 0.53855(14) 0.72697(19) 0.30186(8) 0.0216(4) Uani 1 1 d . . . . .
H30 H 0.5042 0.6560 0.3138 0.026 Uiso 1 1 calc R U . . .
C22 C 0.52779(14) 0.84138(19) 0.32936(8) 0.0245(5) Uani 1 1 d . . . . .
H22 H 0.4861 0.8498 0.3598 0.029 Uiso 1 1 calc R U . . .
C23 C 0.73234(14) 1.13382(18) 0.06413(8) 0.0209(4) Uani 1 1 d . . . . .
H23 H 0.7339 1.2056 0.0387 0.025 Uiso 1 1 calc R U . . .
C24 C 0.64933(14) 1.10815(18) 0.09078(8) 0.0207(4) Uani 1 1 d . . . . .
H24 H 0.5930 1.1622 0.0832 0.025 Uiso 1 1 calc R U . . .
C25 C 0.64756(13) 1.00412(17) 0.12861(8) 0.0177(4) Uani 1 1 d . . . . .
H40 H 0.5887 0.9876 0.1452 0.021 Uiso 1 1 calc R U . . .
C26 C 0.72923(13) 0.92251(17) 0.14329(8) 0.0161(4) Uani 1 1 d . . . . .
C27 C 0.81090(13) 0.95008(17) 0.11382(8) 0.0188(4) Uani 1 1 d . . . . .
H25 H 0.8672 0.8958 0.1207 0.023 Uiso 1 1 calc R U . . .
C28 C 0.81337(14) 1.05260(18) 0.07522(8) 0.0206(4) Uani 1 1 d . . . . .
H26 H 0.8704 1.0672 0.0564 0.025 Uiso 1 1 calc R U . . .
C29 C 0.57903(14) 0.94353(19) 0.31161(8) 0.0231(4) Uani 1 1 d . . . . .
H29 H 0.5729 1.0229 0.3301 0.028 Uiso 1 1 calc R U . . .
C30 C 0.63953(13) 0.92990(18) 0.26677(8) 0.0190(4) Uani 1 1 d . . . . .
H28 H 0.6744 1.0010 0.2556 0.023 Uiso 1 1 calc R U . . .
C31 C 0.70304(13) 0.67966(17) 0.14224(8) 0.0159(4) Uani 1 1 d . . . . .
C32 C 0.60409(14) 0.65619(17) 0.11353(8) 0.0185(4) Uani 1 1 d . . . . .
H35 H 0.5526 0.7097 0.1226 0.022 Uiso 1 1 calc R U . . .
C33 C 0.57842(14) 0.55788(18) 0.07244(8) 0.0213(4) Uani 1 1 d . . . . .
H34 H 0.5105 0.5459 0.0538 0.026 Uiso 1 1 calc R U . . .
C34 C 0.65136(15) 0.47707(18) 0.05848(8) 0.0229(4) Uani 1 1 d . . . . .
H33 H 0.6339 0.4089 0.0309 0.027 Uiso 1 1 calc R U . . .
C35 C 0.74990(14) 0.49762(18) 0.08543(8) 0.0214(4) Uani 1 1 d . . . . .
H31 H 0.8008 0.4433 0.0763 0.026 Uiso 1 1 calc R U . . .
C36 C 0.77472(14) 0.59750(17) 0.12582(8) 0.0184(4) Uani 1 1 d . . . . .
H32 H 0.8431 0.6106 0.1430 0.022 Uiso 1 1 calc R U . . .
C37 C 0.95632(14) 0.65207(19) 0.30513(8) 0.0218(4) Uani 1 1 d . . . . .
H37 H 0.9729 0.5724 0.3232 0.026 Uiso 1 1 calc R U . . .
C38 C 0.86771(13) 0.66766(18) 0.26313(8) 0.0178(4) Uani 1 1 d . . . . .
H36 H 0.8249 0.5976 0.2534 0.021 Uiso 1 1 calc R U . . .
B1 B 0.73064(15) 0.80000(19) 0.18878(9) 0.0152(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 C3 1.330(2) . ?
O1 C2 1.462(2) . ?
O2 C11 1.287(2) . ?
O2 H2 0.8400 . ?
O3 C3 1.206(2) . ?
O4 C11 1.248(2) . ?
N1 C5 1.348(2) . ?
N1 C12 1.349(2) . ?
N1 C6 1.494(2) . ?
C1 C2 1.500(3) . ?
C1 H20 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 H19 0.9900 . ?
C2 H18 0.9900 . ?
C3 C4 1.492(3) . ?
C4 C5 1.376(3) . ?
C4 C14 1.388(3) . ?
C5 H17 0.9500 . ?
C6 C7 1.505(3) . ?
C6 H16 0.9900 . ?
C6 H15 0.9900 . ?
C7 C8 1.520(3) . ?
C7 H13 0.9900 . ?
C7 H14 0.9900 . ?
C8 C9 1.520(3) . ?
C8 H11 0.9900 . ?
C8 H12 0.9900 . ?
C9 C10 1.534(3) . ?
C9 H10 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.494(3) . ?
C10 H8 0.9900 . ?
C10 H7 0.9900 . ?
C12 C13 1.374(3) . ?
C12 H6 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H5 0.9500 . ?
C14 H4 0.9500 . ?
C15 C16 1.384(3) . ?
C15 C37 1.386(3) . ?
C15 H21 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H38 0.9500 . ?
C17 C18 1.402(2) . ?
C17 H39 0.9500 . ?
C18 C38 1.405(2) . ?
C18 B1 1.642(3) . ?
C19 C20 1.403(2) . ?
C19 C30 1.406(3) . ?
C19 B1 1.648(3) . ?
C20 C21 1.389(2) . ?
C20 H27 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H30 0.9500 . ?
C22 C29 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(3) . ?
C23 C28 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.404(2) . ?
C25 H40 0.9500 . ?
C26 C27 1.407(2) . ?
C26 B1 1.644(3) . ?
C27 C28 1.388(3) . ?
C27 H25 0.9500 . ?
C28 H26 0.9500 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9500 . ?
C30 H28 0.9500 . ?
C31 C36 1.403(2) . ?
C31 C32 1.404(2) . ?
C31 B1 1.644(3) . ?
C32 C33 1.389(3) . ?
C32 H35 0.9500 . ?
C33 C34 1.387(3) . ?
C33 H34 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H33 0.9500 . ?
C35 C36 1.391(3) . ?
C35 H31 0.9500 . ?
C36 H32 0.9500 . ?
C37 C38 1.392(2) . ?
C37 H37 0.9500 . ?
C38 H36 0.9500 . ?

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
C3 O1 C2 115.78(15) . . ?
C11 O2 H2 109.5 . . ?
C5 N1 C12 120.53(16) . . ?
C5 N1 C6 116.58(15) . . ?
C12 N1 C6 122.86(16) . . ?
C2 C1 H20 109.5 . . ?
C2 C1 H3 109.5 . . ?
H20 C1 H3 109.5 . . ?
C2 C1 H1 109.5 . . ?
H20 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C1 106.62(17) . . ?
O1 C2 H19 110.4 . . ?
C1 C2 H19 110.4 . . ?
O1 C2 H18 110.4 . . ?
C1 C2 H18 110.4 . . ?
H19 C2 H18 108.6 . . ?
O3 C3 O1 125.42(18) . . ?
O3 C3 C4 123.09(18) . . ?
O1 C3 C4 111.49(16) . . ?
C5 C4 C14 119.24(18) . . ?
C5 C4 C3 121.16(17) . . ?
C14 C4 C3 119.58(17) . . ?
N1 C5 C4 120.74(17) . . ?
N1 C5 H17 119.6 . . ?
C4 C5 H17 119.6 . . ?
N1 C6 C7 114.84(15) . . ?
N1 C6 H16 108.6 . . ?
C7 C6 H16 108.6 . . ?
N1 C6 H15 108.6 . . ?
C7 C6 H15 108.6 . . ?
H16 C6 H15 107.5 . . ?
C6 C7 C8 109.43(15) . . ?
C6 C7 H13 109.8 . . ?
C8 C7 H13 109.8 . . ?
C6 C7 H14 109.8 . . ?
C8 C7 H14 109.8 . . ?
H13 C7 H14 108.2 . . ?
C9 C8 C7 112.47(16) . . ?
C9 C8 H11 109.1 . . ?
C7 C8 H11 109.1 . . ?
C9 C8 H12 109.1 . . ?
C7 C8 H12 109.1 . . ?
H11 C8 H12 107.8 . . ?
C8 C9 C10 111.28(16) . . ?
C8 C9 H10 109.4 . . ?
C10 C9 H10 109.4 . . ?
C8 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
H10 C9 H9 108.0 . . ?
C11 C10 C9 109.78(16) . . ?
C11 C10 H8 109.7 . . ?
C9 C10 H8 109.7 . . ?
C11 C10 H7 109.7 . . ?
C9 C10 H7 109.7 . . ?
H8 C10 H7 108.2 . . ?
O4 C11 O2 123.54(18) . . ?
O4 C11 C10 120.24(19) . . ?
O2 C11 C10 116.15(18) . . ?
N1 C12 C13 120.64(18) . . ?
N1 C12 H6 119.7 . . ?
C13 C12 H6 119.7 . . ?
C12 C13 C14 119.58(18) . . ?
C12 C13 H5 120.2 . . ?
C14 C13 H5 120.2 . . ?
C13 C14 C4 119.25(18) . . ?
C13 C14 H4 120.4 . . ?
C4 C14 H4 120.4 . . ?
C16 C15 C37 118.82(17) . . ?
C16 C15 H21 120.6 . . ?
C37 C15 H21 120.6 . . ?
C15 C16 C17 120.38(18) . . ?
C15 C16 H38 119.8 . . ?
C17 C16 H38 119.8 . . ?
C16 C17 C18 122.63(18) . . ?
C16 C17 H39 118.7 . . ?
C18 C17 H39 118.7 . . ?
C17 C18 C38 115.24(16) . . ?
C17 C18 B1 123.23(16) . . ?
C38 C18 B1 121.30(16) . . ?
C20 C19 C30 115.27(16) . . ?
C20 C19 B1 123.01(16) . . ?
C30 C19 B1 121.41(16) . . ?
C21 C20 C19 122.28(18) . . ?
C21 C20 H27 118.9 . . ?
C19 C20 H27 118.9 . . ?
C22 C21 C20 120.94(18) . . ?
C22 C21 H30 119.5 . . ?
C20 C21 H30 119.5 . . ?
C21 C22 C29 118.65(17) . . ?
C21 C22 H22 120.7 . . ?
C29 C22 H22 120.7 . . ?
C24 C23 C28 118.69(17) . . ?
C24 C23 H23 120.7 . . ?
C28 C23 H23 120.7 . . ?
C23 C24 C25 120.64(17) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 122.68(17) . . ?
C24 C25 H40 118.7 . . ?
C26 C25 H40 118.7 . . ?
C25 C26 C27 114.72(16) . . ?
C25 C26 B1 124.08(16) . . ?
C27 C26 B1 121.16(16) . . ?
C28 C27 C26 123.27(17) . . ?
C28 C27 H25 118.4 . . ?
C26 C27 H25 118.4 . . ?
C27 C28 C23 119.90(17) . . ?
C27 C28 H26 120.0 . . ?
C23 C28 H26 120.0 . . ?
C22 C29 C30 120.05(18) . . ?
C22 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C19 122.81(18) . . ?
C29 C30 H28 118.6 . . ?
C19 C30 H28 118.6 . . ?
C36 C31 C32 115.16(16) . . ?
C36 C31 B1 123.72(16) . . ?
C32 C31 B1 121.04(16) . . ?
C33 C32 C31 122.65(17) . . ?
C33 C32 H35 118.7 . . ?
C31 C32 H35 118.7 . . ?
C34 C33 C32 120.36(18) . . ?
C34 C33 H34 119.8 . . ?
C32 C33 H34 119.8 . . ?
C35 C34 C33 118.77(18) . . ?
C35 C34 H33 120.6 . . ?
C33 C34 H33 120.6 . . ?
C34 C35 C36 120.24(18) . . ?
C34 C35 H31 119.9 . . ?
C36 C35 H31 119.9 . . ?
C35 C36 C31 122.79(17) . . ?
C35 C36 H32 118.6 . . ?
C31 C36 H32 118.6 . . ?
C15 C37 C38 120.24(18) . . ?
C15 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C18 122.67(18) . . ?
C37 C38 H36 118.7 . . ?
C18 C38 H36 118.7 . . ?
C18 B1 C26 112.02(15) . . ?
C18 B1 C31 112.08(15) . . ?
C26 B1 C31 105.69(14) . . ?
C18 B1 C19 103.49(13) . . ?
C26 B1 C19 111.79(15) . . ?
C31 B1 C19 111.95(15) . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_brcooh
_database_code_depnum_ccdc_archive 'CCDC 1533668'
_audit_update_record             
;
2017-02-20 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 Br N2 O3'
_chemical_formula_weight         345.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6544(2)
_cell_length_b                   10.3806(3)
_cell_length_c                   10.4938(3)
_cell_angle_alpha                105.5910(13)
_cell_angle_beta                 102.9580(12)
_cell_angle_gamma                95.4460(13)
_cell_volume                     771.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3151
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      26.40

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.485
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12734
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3151
_reflns_number_gt                2951
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.7413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0588
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.158
_refine_ls_shift/su_mean         0.007

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.29138(3) 0.13971(2) 0.23224(2) 0.01860(10) Uani 1 1 d . . .
C1 C 0.3336(3) 1.0497(3) 0.6897(3) 0.0219(5) Uani 1 1 d . . .
H1 H 0.4413 1.0127 0.7112 0.026 Uiso 1 1 calc R . .
C2 C 0.3097(3) 1.1139(3) 0.5903(3) 0.0213(5) Uani 1 1 d . . .
H2 H 0.3988 1.1188 0.5409 0.026 Uiso 1 1 calc R . .
C3 C 0.1549(3) 1.1720(2) 0.5618(3) 0.0170(5) Uani 1 1 d . . .
H3 H 0.1383 1.2187 0.4946 0.020 Uiso 1 1 calc R . .
C4 C 0.0248(3) 1.1606(2) 0.6333(2) 0.0147(5) Uani 1 1 d . . .
C5 C 0.0521(3) 1.0920(2) 0.7302(2) 0.0170(5) Uani 1 1 d . . .
H5 H -0.0376 1.0824 0.7780 0.020 Uiso 1 1 calc R . .
C6 C -0.1464(3) 1.2197(2) 0.6131(2) 0.0169(5) Uani 1 1 d . . .
C7 C -0.3007(3) 1.3757(3) 0.5230(3) 0.0214(5) Uani 1 1 d . . .
H7A H -0.3412 1.4020 0.6083 0.026 Uiso 1 1 calc R . .
H7B H -0.4018 1.3136 0.4495 0.026 Uiso 1 1 calc R . .
C8 C -0.2458(4) 1.4986(3) 0.4836(3) 0.0302(6) Uani 1 1 d . . .
H8A H -0.1480 1.5602 0.5582 0.045 Uiso 1 1 calc R . .
H8B H -0.3505 1.5448 0.4661 0.045 Uiso 1 1 calc R . .
H8C H -0.2029 1.4713 0.4005 0.045 Uiso 1 1 calc R . .
C9 C 0.2359(4) 0.9741(3) 0.8695(3) 0.0279(6) Uani 1 1 d . . .
H9A H 0.1493 0.9991 0.9257 0.033 Uiso 1 1 calc R . .
H9B H 0.3602 1.0109 0.9293 0.033 Uiso 1 1 calc R . .
C10 C 0.2151(4) 0.8207(3) 0.8195(3) 0.0198(5) Uani 1 1 d . . .
H10A H 0.3065 0.7936 0.7684 0.024 Uiso 1 1 calc R . .
H10B H 0.0926 0.7820 0.7573 0.024 Uiso 1 1 calc R . .
C11 C 0.2421(5) 0.7681(3) 0.9434(3) 0.0323(7) Uani 1 1 d . . .
H11A H 0.3620 0.8132 1.0067 0.039 Uiso 1 1 calc R . .
H11B H 0.1483 0.7958 0.9918 0.039 Uiso 1 1 calc R . .
C12 C 0.2334(4) 0.6161(3) 0.9141(3) 0.0257(6) Uani 1 1 d . . .
H12A H 0.3269 0.5860 0.8663 0.031 Uiso 1 1 calc R . .
H12B H 0.1127 0.5688 0.8539 0.031 Uiso 1 1 calc R . .
C13 C 0.2661(5) 0.5808(3) 1.0482(3) 0.0368(8) Uani 1 1 d . . .
H13A H 0.3860 0.6313 1.1072 0.044 Uiso 1 1 calc R . .
H13B H 0.1731 0.6142 1.0950 0.044 Uiso 1 1 calc R . .
C14 C 0.2622(4) 0.4340(3) 1.0387(3) 0.0288(6) Uani 1 1 d . . .
N1 N 0.2038(3) 1.0387(2) 0.7574(2) 0.0186(4) Uani 1 1 d . . .
O4 O 0.2868(5) 0.4171(3) 1.1620(2) 0.0482(8) Uani 1 1 d . . .
O1 O -0.2718(3) 1.1884(2) 0.6565(2) 0.0263(4) Uani 1 1 d . . .
O2 O -0.1406(2) 1.30915(18) 0.54396(19) 0.0203(4) Uani 1 1 d . . .
O3 O 0.2426(4) 0.3431(2) 0.9365(2) 0.0522(7) Uani 1 1 d . . .
H41 H 0.311(6) 0.359(5) 1.158(5) 0.056(15) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.358(3) . ?
C1 C2 1.370(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 C6 1.495(3) . ?
C5 N1 1.339(3) . ?
C5 H5 0.9500 . ?
C6 O1 1.205(3) . ?
C6 O2 1.326(3) . ?
C7 O2 1.465(3) . ?
C7 C8 1.496(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.490(3) . ?
C9 C10 1.516(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.497(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.191(4) . ?
C14 O4 1.327(4) . ?
O4 H41 0.64(4) . ?

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
N1 C1 C2 120.3(2) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 C6 116.7(2) . . ?
C3 C4 C6 123.9(2) . . ?
N1 C5 C4 120.7(2) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
O1 C6 O2 125.4(2) . . ?
O1 C6 C4 122.7(2) . . ?
O2 C6 C4 111.9(2) . . ?
O2 C7 C8 106.9(2) . . ?
O2 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O2 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 114.0(2) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 108.3(2) . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C12 C11 C10 116.1(2) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 109.5(2) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 116.8(2) . . ?
C14 C13 H13A 108.1 . . ?
C12 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C12 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
O3 C14 O4 123.4(3) . . ?
O3 C14 C13 126.1(3) . . ?
O4 C14 C13 110.5(2) . . ?
C5 N1 C1 120.9(2) . . ?
C5 N1 C9 119.5(2) . . ?
C1 N1 C9 119.5(2) . . ?
C14 O4 H41 107(4) . . ?
C6 O2 C7 115.73(19) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.115
