# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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 
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data_mx5495
_database_code_depnum_ccdc_archive 'CCDC 1879727'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2017-01-06
_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         'C15 H18 Br N O4'
_chemical_formula_sum            'C15 H18 Br N O4'
_chemical_formula_weight         356.21
_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      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                   5.0429(10)
_cell_length_b                   11.880(2)
_cell_length_c                   25.830(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1547.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4672
_cell_measurement_theta_min      1.5767
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.63799
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.077
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10042
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         1.577
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 99.0000
_diffrn_measured_fraction_theta_max 27.4672
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9102
	          2theta: -19.9443
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9102
	          2theta: -19.9443
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2099
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.1940
_diffrn_orient_matrix_UB_12      0.0137
_diffrn_orient_matrix_UB_13      -0.0385
_diffrn_orient_matrix_UB_21      0.0164
_diffrn_orient_matrix_UB_22      -0.0002
_diffrn_orient_matrix_UB_23      0.0826
_diffrn_orient_matrix_UB_31      0.0026
_diffrn_orient_matrix_UB_32      -0.0386
_diffrn_orient_matrix_UB_33      -0.0006
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3356
_reflns_number_total             3470
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.066
_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)+(0.0207P)²+0.4293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1C), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br1 Br 0.18447(7) 0.52669(3) 0.47691(2) 0.03675(10) Uani 1 1 d . . . . .
O1 O 0.2107(5) 0.19653(15) 0.26793(7) 0.0288(4) Uani 1 1 d . . . . .
H1 H 0.1270 0.2544 0.2623 0.043 Uiso 1 1 calc GR . . . .
O2 O -0.0335(4) -0.07468(16) 0.26522(7) 0.0254(4) Uani 1 1 d . . . . .
O3 O -0.1887(4) 0.34152(15) 0.35421(8) 0.0283(4) Uani 1 1 d . . . . .
O4 O 0.2162(4) 0.41965(14) 0.35718(7) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.3999(5) -0.0699(2) 0.24484(9) 0.0276(5) Uani 1 1 d . . . . .
H1A H 0.3769 -0.1127 0.2184 0.033 Uiso 1 1 calc R . . . .
H1B H 0.5558 -0.0454 0.2522 0.033 Uiso 1 1 calc R . . . .
C1 C 0.2552(5) 0.0325(2) 0.32067(9) 0.0186(5) Uani 1 1 d . . . . .
H1C H 0.4474 0.0440 0.3226 0.022 Uiso 1 1 calc R . . . .
C2 C 0.1216(5) 0.1476(2) 0.31508(9) 0.0193(5) Uani 1 1 d . . . . .
H2 H -0.0712 0.1375 0.3137 0.023 Uiso 1 1 calc R . . . .
C3 C 0.1929(6) 0.22152(19) 0.36174(9) 0.0199(5) Uani 1 1 d . . . . .
H3 H 0.3845 0.2353 0.3616 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1157(6) 0.1654(2) 0.41311(10) 0.0267(6) Uani 1 1 d . . . . .
H4A H 0.1756 0.2118 0.4417 0.032 Uiso 1 1 calc R . . . .
H4B H -0.0758 0.1593 0.4152 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2387(6) 0.0487(2) 0.41753(10) 0.0287(7) Uani 1 1 d . . . . .
H5A H 0.1772 0.0127 0.4490 0.034 Uiso 1 1 calc R . . . .
H5B H 0.4301 0.0554 0.4195 0.034 Uiso 1 1 calc R . . . .
C6 C 0.1641(6) -0.0236(2) 0.37101(9) 0.0239(5) Uani 1 1 d . . . . .
H6A H -0.0266 -0.0341 0.3702 0.029 Uiso 1 1 calc R . . . .
H6B H 0.2465 -0.0970 0.3742 0.029 Uiso 1 1 calc R . . . .
C7 C 0.1958(5) -0.04169(19) 0.27410(9) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.0497(5) 0.3327(2) 0.35728(9) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.0980(5) 0.5319(2) 0.35578(10) 0.0243(5) Uani 1 1 d . . . . .
H9A H -0.0589 0.5347 0.3775 0.029 Uiso 1 1 calc R . . . .
H9B H 0.0482 0.5517 0.3207 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3048(6) 0.61043(19) 0.37561(9) 0.0211(5) Uani 1 1 d . . . . .
C11 C 0.4504(6) 0.6780(2) 0.34155(10) 0.0239(6) Uani 1 1 d . . . . .
H11 H 0.4139 0.6749 0.3063 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6468(6) 0.7490(2) 0.35912(10) 0.0259(6) Uani 1 1 d . . . . .
H12 H 0.7422 0.7927 0.3358 0.031 Uiso 1 1 calc R . . . .
C13 C 0.7023(7) 0.7554(2) 0.41153(11) 0.0284(6) Uani 1 1 d . . . . .
H13 H 0.8338 0.8039 0.4234 0.034 Uiso 1 1 calc R . . . .
C14 C 0.5626(6) 0.6898(2) 0.44634(10) 0.0277(6) Uani 1 1 d . . . . .
H14 H 0.5991 0.6938 0.4816 0.033 Uiso 1 1 calc R . . . .
C15 C 0.3680(6) 0.6180(2) 0.42803(10) 0.0239(6) 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
Br1 C15 1.905(3) . ?
O1 H1 0.8200 . ?
O1 C2 1.422(3) . ?
O2 C7 1.243(3) . ?
O3 C8 1.209(3) . ?
O4 C8 1.332(3) . ?
O4 C9 1.461(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.320(3) . ?
C1 H1C 0.9800 . ?
C1 C2 1.531(3) . ?
C1 C6 1.532(3) . ?
C1 C7 1.521(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.534(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.535(3) . ?
C3 C8 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.523(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.524(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.490(4) . ?
C10 C11 1.399(4) . ?
C10 C15 1.394(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(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
C2 O1 H1 109.5 . . ?
C8 O4 C9 116.8(2) . . ?
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 H1C 108.4 . . ?
C2 C1 C6 109.7(2) . . ?
C6 C1 H1C 108.4 . . ?
C7 C1 H1C 108.4 . . ?
C7 C1 C2 110.86(19) . . ?
C7 C1 C6 111.1(2) . . ?
O1 C2 C1 107.9(2) . . ?
O1 C2 H2 109.4 . . ?
O1 C2 C3 111.4(2) . . ?
C1 C2 H2 109.4 . . ?
C1 C2 C3 109.5(2) . . ?
C3 C2 H2 109.4 . . ?
C2 C3 H3 109.0 . . ?
C2 C3 C4 111.8(2) . . ?
C4 C3 H3 109.0 . . ?
C8 C3 C2 109.2(2) . . ?
C8 C3 H3 109.0 . . ?
C8 C3 C4 108.9(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.7(2) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 C1 110.5(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O2 C7 N1 122.7(2) . . ?
O2 C7 C1 120.8(2) . . ?
N1 C7 C1 116.5(2) . . ?
O3 C8 O4 124.0(2) . . ?
O3 C8 C3 123.8(2) . . ?
O4 C8 C3 112.2(2) . . ?
O4 C9 H9A 110.5 . . ?
O4 C9 H9B 110.5 . . ?
O4 C9 C10 106.1(2) . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
C11 C10 C9 120.7(2) . . ?
C15 C10 C9 122.3(2) . . ?
C15 C10 C11 117.0(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 Br1 119.7(2) . . ?
C14 C15 Br1 118.0(2) . . ?
C14 C15 C10 122.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 2.20 2.987(3) 160.2 3
N1 H1A O3 0.86 2.17 2.965(3) 153.3 3_545
N1 H1B O2 0.86 2.13 2.906(3) 150.5 1_655

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 C3 C4 -175.8(2) . . . . ?
O1 C2 C3 C8 63.6(3) . . . . ?
O4 C9 C10 C11 102.8(3) . . . . ?
O4 C9 C10 C15 -75.3(3) . . . . ?
C1 C2 C3 C4 -56.6(3) . . . . ?
C1 C2 C3 C8 -177.2(2) . . . . ?
C2 C1 C6 C5 -60.2(3) . . . . ?
C2 C1 C7 O2 -65.9(3) . . . . ?
C2 C1 C7 N1 115.2(2) . . . . ?
C2 C3 C4 C5 54.9(3) . . . . ?
C2 C3 C8 O3 57.8(3) . . . . ?
C2 C3 C8 O4 -122.3(2) . . . . ?
C3 C4 C5 C6 -55.1(3) . . . . ?
C4 C3 C8 O3 -64.5(3) . . . . ?
C4 C3 C8 O4 115.4(2) . . . . ?
C4 C5 C6 C1 58.2(3) . . . . ?
C6 C1 C2 O1 -179.9(2) . . . . ?
C6 C1 C2 C3 58.8(3) . . . . ?
C6 C1 C7 O2 56.3(3) . . . . ?
C6 C1 C7 N1 -122.5(2) . . . . ?
C7 C1 C2 O1 -56.8(3) . . . . ?
C7 C1 C2 C3 -178.1(2) . . . . ?
C7 C1 C6 C5 176.9(2) . . . . ?
C8 O4 C9 C10 159.2(2) . . . . ?
C8 C3 C4 C5 175.6(2) . . . . ?
C9 O4 C8 O3 3.1(4) . . . . ?
C9 O4 C8 C3 -176.8(2) . . . . ?
C9 C10 C11 C12 -178.4(3) . . . . ?
C9 C10 C15 Br1 -0.6(4) . . . . ?
C9 C10 C15 C14 179.0(3) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C10 C15 Br1 -178.7(2) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 Br1 178.8(2) . . . . ?
C13 C14 C15 C10 -0.9(4) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?

_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_mx5570a_pl
_database_code_depnum_ccdc_archive 'CCDC 1879728'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2017-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 Br N O4'
_chemical_formula_sum            'C15 H18 Br N O4'
_chemical_formula_weight         356.21
_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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.5631(14)
_cell_length_b                   12.796(3)
_cell_length_c                   18.385(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1544.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4148
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4782
_cell_measurement_theta_min      1.5914
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.543
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9663
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.939
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3160
_reflns_number_total             3524
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.008(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.147
_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)+(0.0212P)²+0.3770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.992(14) 0.008(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1C)
;
_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 0.99197(8) 0.54275(4) 0.12205(2) 0.04368(15) Uani 1 1 d . . . . .
C1 C -0.0002(7) 0.5052(3) 0.43558(18) 0.0250(7) Uani 1 1 d . . . . .
H1 H -0.1137 0.4822 0.4030 0.030 Uiso 1 1 calc R . . . .
N1 N -0.2610(5) 0.6250(3) 0.4788(2) 0.0331(9) Uani 1 1 d . . . . .
H1A H -0.3034 0.6819 0.5011 0.040 Uiso 1 1 calc R . . . .
H1B H -0.3499 0.5802 0.4613 0.040 Uiso 1 1 calc R . . . .
O1 O 0.3546(4) 0.5614(2) 0.43107(17) 0.0371(8) Uani 1 1 d . . . . .
H1C H 0.3114 0.6077 0.4595 0.056 Uiso 1 1 calc GR . . . .
C2 C 0.1898(6) 0.5222(3) 0.3886(2) 0.0256(9) Uani 1 1 d . . . . .
H2 H 0.1575 0.5733 0.3491 0.031 Uiso 1 1 calc R . . . .
O2 O 0.0650(4) 0.6689(3) 0.4962(2) 0.0493(9) Uani 1 1 d . . . . .
C3 C 0.2618(6) 0.4197(3) 0.3547(2) 0.0274(9) Uani 1 1 d . . . . .
H3 H 0.1514 0.3943 0.3216 0.033 Uiso 1 1 calc R . . . .
O3 O 0.6128(5) 0.3963(2) 0.31778(17) 0.0412(8) Uani 1 1 d . . . . .
C4 C 0.2965(7) 0.3359(3) 0.4127(2) 0.0368(11) Uani 1 1 d . . . . .
H4A H 0.3354 0.2695 0.3888 0.044 Uiso 1 1 calc R . . . .
H4B H 0.4102 0.3575 0.4447 0.044 Uiso 1 1 calc R . . . .
O4 O 0.4138(4) 0.5076(3) 0.25593(16) 0.0369(8) Uani 1 1 d . . . . .
C5 C 0.1072(7) 0.3187(4) 0.4580(3) 0.0415(12) Uani 1 1 d . . . . .
H5A H 0.1370 0.2671 0.4967 0.050 Uiso 1 1 calc R . . . .
H5B H -0.0021 0.2897 0.4269 0.050 Uiso 1 1 calc R . . . .
C6 C 0.0331(7) 0.4205(3) 0.4929(2) 0.0325(10) Uani 1 1 d . . . . .
H6A H -0.0962 0.4075 0.5191 0.039 Uiso 1 1 calc R . . . .
H6B H 0.1351 0.4449 0.5287 0.039 Uiso 1 1 calc R . . . .
C7 C -0.0635(6) 0.6069(3) 0.4719(2) 0.0296(10) Uani 1 1 d . . . . .
C8 C 0.4488(6) 0.4371(3) 0.3093(2) 0.0296(10) Uani 1 1 d . . . . .
C9 C 0.5800(7) 0.5286(4) 0.2071(2) 0.0420(12) Uani 1 1 d . . . . .
H9A H 0.5244 0.5524 0.1598 0.050 Uiso 1 1 calc R . . . .
H9B H 0.6563 0.4630 0.1984 0.050 Uiso 1 1 calc R . . . .
C10 C 0.7239(7) 0.6099(3) 0.2357(2) 0.0328(10) Uani 1 1 d . . . . .
C11 C 0.9151(7) 0.6253(4) 0.2039(2) 0.0344(11) Uani 1 1 d . . . . .
C12 C 1.0481(8) 0.7005(4) 0.2278(2) 0.0419(12) Uani 1 1 d . . . . .
H12 H 1.1765 0.7090 0.2046 0.050 Uiso 1 1 calc R . . . .
C13 C 0.9948(10) 0.7636(3) 0.2853(2) 0.0477(12) Uani 1 1 d . . . . .
H13 H 1.0870 0.8152 0.3026 0.057 Uiso 1 1 calc R . . . .
C14 C 0.8043(9) 0.7513(4) 0.3181(3) 0.0483(14) Uani 1 1 d . . . . .
H14 H 0.7655 0.7953 0.3574 0.058 Uiso 1 1 calc R . . . .
C15 C 0.6726(8) 0.6751(4) 0.2933(2) 0.0414(12) Uani 1 1 d . . . . .
H15 H 0.5437 0.6670 0.3161 0.050 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
Br1 C11 1.906(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.532(6) . ?
C1 C6 1.527(5) . ?
C1 C7 1.520(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C7 1.323(5) . ?
O1 H1C 0.8400 . ?
O1 C2 1.424(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.528(5) . ?
O2 C7 1.241(5) . ?
C3 H3 1.0000 . ?
C3 C4 1.529(6) . ?
C3 C8 1.500(5) . ?
O3 C8 1.207(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.512(6) . ?
O4 C8 1.353(5) . ?
O4 C9 1.438(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.531(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.501(6) . ?
C10 C11 1.399(6) . ?
C10 C15 1.388(6) . ?
C11 C12 1.371(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.397(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(7) . ?
C15 H15 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
C2 C1 H1 108.1 . . ?
C6 C1 H1 108.1 . . ?
C6 C1 C2 111.9(4) . . ?
C7 C1 H1 108.1 . . ?
C7 C1 C2 110.4(3) . . ?
C7 C1 C6 110.1(3) . . ?
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 O1 H1C 109.5 . . ?
C1 C2 H2 109.2 . . ?
O1 C2 C1 111.1(3) . . ?
O1 C2 H2 109.2 . . ?
O1 C2 C3 106.9(3) . . ?
C3 C2 C1 111.1(3) . . ?
C3 C2 H2 109.2 . . ?
C2 C3 H3 107.7 . . ?
C2 C3 C4 111.3(3) . . ?
C4 C3 H3 107.7 . . ?
C8 C3 C2 110.7(3) . . ?
C8 C3 H3 107.7 . . ?
C8 C3 C4 111.7(3) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.4(4) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C8 O4 C9 116.7(3) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.6(4) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C1 C6 C5 111.1(3) . . ?
C1 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C1 117.4(4) . . ?
O2 C7 C1 121.2(4) . . ?
O2 C7 N1 121.3(4) . . ?
O3 C8 C3 126.5(4) . . ?
O3 C8 O4 122.2(4) . . ?
O4 C8 C3 111.3(3) . . ?
O4 C9 H9A 109.0 . . ?
O4 C9 H9B 109.0 . . ?
O4 C9 C10 112.8(4) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C11 C10 C9 121.0(4) . . ?
C15 C10 C9 122.1(4) . . ?
C15 C10 C11 116.9(4) . . ?
C10 C11 Br1 119.3(3) . . ?
C12 C11 Br1 118.2(3) . . ?
C12 C11 C10 122.4(4) . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(5) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.7(5) . . ?
C14 C15 H15 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.88 2.10 2.911(5) 153.5 3_466
N1 H1B O1 0.88 2.03 2.793(4) 144.2 1_455
O1 H1C O2 0.84 1.92 2.634(4) 142.3 .

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
Br1 C11 C12 C13 178.0(3) . . . . ?
C1 C2 C3 C4 -54.7(4) . . . . ?
C1 C2 C3 C8 -179.5(3) . . . . ?
O1 C2 C3 C4 66.6(4) . . . . ?
O1 C2 C3 C8 -58.2(4) . . . . ?
C2 C1 C6 C5 -54.1(5) . . . . ?
C2 C1 C7 N1 143.3(4) . . . . ?
C2 C1 C7 O2 -39.1(5) . . . . ?
C2 C3 C4 C5 55.9(5) . . . . ?
C2 C3 C8 O3 120.8(5) . . . . ?
C2 C3 C8 O4 -58.4(4) . . . . ?
C3 C4 C5 C6 -55.9(5) . . . . ?
C4 C3 C8 O3 -3.8(6) . . . . ?
C4 C3 C8 O4 177.0(3) . . . . ?
C4 C5 C6 C1 54.9(5) . . . . ?
O4 C9 C10 C11 166.5(4) . . . . ?
O4 C9 C10 C15 -15.3(6) . . . . ?
C6 C1 C2 O1 -64.6(4) . . . . ?
C6 C1 C2 C3 54.2(4) . . . . ?
C6 C1 C7 N1 -92.7(5) . . . . ?
C6 C1 C7 O2 85.0(5) . . . . ?
C7 C1 C2 O1 58.4(4) . . . . ?
C7 C1 C2 C3 177.2(3) . . . . ?
C7 C1 C6 C5 -177.2(4) . . . . ?
C8 C3 C4 C5 -179.9(4) . . . . ?
C8 O4 C9 C10 -84.9(5) . . . . ?
C9 O4 C8 C3 -178.0(3) . . . . ?
C9 O4 C8 O3 2.7(6) . . . . ?
C9 C10 C11 Br1 0.9(6) . . . . ?
C9 C10 C11 C12 178.5(4) . . . . ?
C9 C10 C15 C14 -178.5(4) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C10 C15 C14 -0.2(7) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 C10 -0.4(7) . . . . ?
C15 C10 C11 Br1 -177.4(3) . . . . ?
C15 C10 C11 C12 0.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.992(14)
2 0.008(14)

