# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_lqj-20200118-1
_database_code_depnum_ccdc_archive 'CCDC 2106472'
loop_
_audit_author_name
_audit_author_address
'Zhenghuan Lin'
;Fujian Normal University
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2020-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(Cl), 2(C9 H12 N O2)'
_chemical_formula_sum            'C18 H24 Cl2 N2 O4'
_chemical_formula_weight         403.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
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'
Cl Cl 0.1484 0.1585 '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           29
_space_group_name_H-M_alt        'P b c 21'
_space_group_name_Hall           'P 2c -2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, z'
'x, -y+1/2, z+1/2'

_cell_length_a                   5.97246(16)
_cell_length_b                   9.0205(2)
_cell_length_c                   36.0997(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1944.86(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4933
_cell_measurement_temperature    292.9(6)
_cell_measurement_theta_max      72.7540
_cell_measurement_theta_min      3.6110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             848
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            11866
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.051
_diffrn_reflns_theta_min         2.254
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5148
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  34.00   1.00    7.50    --  -40.45  38.00-120.00   99
  2  ω   -113.00 -12.00   1.00    7.50    --  -40.45 -57.00 -60.00  101
  3  ω    -69.00  33.00   1.00    7.50    --  -40.45  57.00  90.00  102
  4  ω    -92.00  -2.00   1.00    7.50    --  -40.45 125.00 150.00   90
  5  ω     48.00 108.00   1.00   15.00    --  103.24 -94.00  60.00   60
  6  ω     30.00  56.00   1.00   15.00    --  103.24 -30.00-180.00   26
  7  ω     33.00  75.00   1.00   15.00    --  103.24-125.00  30.00   42
  8  ω     38.00  91.00   1.00   15.00    --  103.24 -94.00 150.00   53
  9  ω     39.00 117.00   1.00   15.00    --  103.24-125.00  60.00   78
 10  ω     27.00 135.00   1.00   15.00    --  103.24 -77.00-150.00  108
 11  ω     51.00  81.00   1.00   15.00    --  103.24  15.00 -30.00   30
 12  ω    146.00 171.00   1.00   15.00    --  103.24 125.00-150.00   25
 13  ω     68.00 132.00   1.00   15.00    --  103.24 -30.00-180.00   64
 14  ω     39.00  65.00   1.00   15.00    --  103.24-125.00-120.00   26
 15  ω     95.00 177.00   1.00   15.00    --  103.24  30.00-180.00   82
 16  ω    126.00 152.00   1.00   15.00    --  103.24  15.00 -30.00   26
 17  ω     30.00 126.00   1.00   15.00    --  103.24 -30.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0715588000
_diffrn_orient_matrix_UB_12      -0.0479649000
_diffrn_orient_matrix_UB_13      0.0391964000
_diffrn_orient_matrix_UB_21      -0.2243933000
_diffrn_orient_matrix_UB_22      -0.0818304000
_diffrn_orient_matrix_UB_23      0.0049521000
_diffrn_orient_matrix_UB_31      0.1052489000
_diffrn_orient_matrix_UB_32      -0.1420283000
_diffrn_orient_matrix_UB_33      -0.0161175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3476
_reflns_number_total             3720
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details 
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.69(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0884
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1670P)²+2.4771P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2492
_refine_ls_wR_factor_ref         0.2533
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B), C19(H19A,H19B), C9(H9A,H9B), C18(H18A,H18B),
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C21(H21), C22(H22), C11(H11), C15(H15), C23(H23)
2.c Idealised Me refined as rotating group:
 N20(H20A,H20B,H20C), N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.5041(2) 0.80744(19) 0.00719(5) 0.0365(6) Uani 1 1 d . . . . .
Cl2 Cl 0.9954(2) 0.9357(2) -0.06113(5) 0.0371(6) Uani 1 1 d . . . . .
C4 C 0.5178(16) 1.3191(10) -0.2109(3) 0.047(3) Uani 1 1 d . . . . .
O6 O 0.7425(11) 1.4707(8) -0.2432(2) 0.0630(17) Uani 1 1 d . . . . .
C7 C 0.6201(15) 1.1850(8) -0.1569(3) 0.0467(18) Uani 1 1 d . . . . .
O10 O 0.3892(13) 1.3662(10) -0.2398(3) 0.075(2) Uani 1 1 d . . . . .
C12 C 0.555(2) 1.0798(9) -0.1255(3) 0.053(2) Uani 1 1 d . . . . .
H12A H 0.4184 1.0275 -0.1320 0.064 Uiso 1 1 calc R . . . .
H12B H 0.6723 1.0072 -0.1218 0.064 Uiso 1 1 calc R . . . .
C14 C 0.8295(14) 1.2522(11) -0.1585(3) 0.055(2) Uani 1 1 d . . . . .
H14 H 0.9349 1.2316 -0.1402 0.066 Uiso 1 1 calc R . . . .
C16 C 0.7228(14) 1.3804(9) -0.2126(3) 0.0500(19) Uani 1 1 d . . . . .
C17 C 0.5186(14) 1.1663(9) -0.0902(3) 0.040(2) Uani 1 1 d . . . . .
H17A H 0.6449 1.2318 -0.0861 0.048 Uiso 1 1 calc R . . . .
H17B H 0.3852 1.2268 -0.0927 0.048 Uiso 1 1 calc R . . . .
C19 C 0.5209(17) 1.4706(14) -0.2593(3) 0.054(2) Uani 1 1 d . . . . .
H19A H 0.4548 1.5685 -0.2573 0.065 Uiso 1 1 calc R . . . .
H19B H 0.5288 1.4440 -0.2853 0.065 Uiso 1 1 calc R . . . .
N20 N 0.4936(9) 1.0660(7) -0.0582(3) 0.0332(18) Uani 1 1 d . . . . .
H20A H 0.3643 1.0175 -0.0600 0.040 Uiso 1 1 calc GR . . . .
H20B H 0.4953 1.1187 -0.0374 0.040 Uiso 1 1 calc GR . . . .
H20C H 0.6061 1.0013 -0.0580 0.040 Uiso 1 1 calc GR . . . .
C21 C 0.4655(17) 1.2192(10) -0.1835(3) 0.0462(19) Uani 1 1 d . . . . .
H21 H 0.3250 1.1747 -0.1831 0.055 Uiso 1 1 calc R . . . .
C22 C 0.8851(15) 1.3519(11) -0.1876(3) 0.058(2) Uani 1 1 d . . . . .
H22 H 1.0261 1.3951 -0.1893 0.069 Uiso 1 1 calc R . . . .
C1 C 0.1106(13) 0.0582(7) 0.1029(2) 0.0372(15) Uani 1 1 d . . . . .
N2 N -0.0068(9) 0.1748(7) 0.0026(2) 0.0336(18) Uani 1 1 d . . . . .
H2A H -0.0082 0.1216 -0.0181 0.040 Uiso 1 1 calc GR . . . .
H2B H 0.1074 0.2381 0.0021 0.040 Uiso 1 1 calc GR . . . .
H2C H -0.1346 0.2249 0.0046 0.040 Uiso 1 1 calc GR . . . .
C3 C 0.2120(14) -0.1347(8) 0.1589(2) 0.0419(16) Uani 1 1 d . . . . .
O5 O 0.2190(12) -0.2255(7) 0.1894(2) 0.0578(15) Uani 1 1 d . . . . .
O8 O -0.1342(12) -0.1224(8) 0.1845(2) 0.0644(18) Uani 1 1 d . . . . .
C9 C 0.0572(18) 0.1622(8) 0.0707(3) 0.0444(17) Uani 1 1 d . . . . .
H9A H 0.1805 0.2307 0.0671 0.053 Uiso 1 1 calc R . . . .
H9B H -0.0757 0.2195 0.0765 0.053 Uiso 1 1 calc R . . . .
C11 C -0.0537(16) 0.0209(9) 0.1282(3) 0.0434(17) Uani 1 1 d . . . . .
H11 H -0.1973 0.0599 0.1261 0.052 Uiso 1 1 calc R . . . .
C13 C -0.0017(10) -0.0734(8) 0.1559(3) 0.033(2) Uani 1 1 d . . . . .
C15 C 0.3757(14) -0.1038(12) 0.1336(3) 0.056(2) Uani 1 1 d . . . . .
H15 H 0.5174 -0.1459 0.1354 0.067 Uiso 1 1 calc R . . . .
C18 C 0.0183(13) 0.0739(8) 0.0351(3) 0.0345(18) Uani 1 1 d . . . . .
H18A H 0.1436 0.0076 0.0310 0.041 Uiso 1 1 calc R . . . .
H18B H -0.1158 0.0142 0.0378 0.041 Uiso 1 1 calc R . . . .
C23 C 0.3201(14) -0.0059(10) 0.1050(3) 0.0527(19) Uani 1 1 d . . . . .
H23 H 0.4264 0.0164 0.0870 0.063 Uiso 1 1 calc R . . . .
C25 C -0.0032(16) -0.2189(14) 0.2062(3) 0.055(3) Uani 1 1 d . . . . .
H25A H -0.0701 -0.3169 0.2067 0.066 Uiso 1 1 calc R . . . .
H25B H 0.0071 -0.1824 0.2314 0.066 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
C4 O10 1.362(13) . ?
C4 C16 1.345(13) . ?
C4 C21 1.373(14) . ?
O6 C16 1.379(11) . ?
O6 C19 1.445(12) . ?
C7 C12 1.529(13) . ?
C7 C14 1.391(13) . ?
C7 C21 1.370(13) . ?
O10 C19 1.415(13) . ?
C12 C17 1.507(13) . ?
C14 C22 1.422(13) . ?
C16 C22 1.349(14) . ?
C17 N20 1.474(15) . ?
C1 C9 1.527(10) . ?
C1 C11 1.382(12) . ?
C1 C23 1.380(11) . ?
N2 C18 1.492(12) . ?
C3 O5 1.372(9) . ?
C3 C13 1.395(10) . ?
C3 C15 1.366(12) . ?
O5 C25 1.460(12) . ?
O8 C13 1.377(12) . ?
O8 C25 1.407(13) . ?
C9 C18 1.529(12) . ?
C11 C13 1.348(13) . ?
C15 C23 1.400(13) . ?

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
O10 C4 C21 128.8(9) . . ?
C16 C4 O10 110.6(10) . . ?
C16 C4 C21 120.6(9) . . ?
C16 O6 C19 104.1(7) . . ?
C14 C7 C12 122.1(9) . . ?
C21 C7 C12 119.3(9) . . ?
C21 C7 C14 118.6(8) . . ?
C4 O10 C19 105.9(8) . . ?
C17 C12 C7 109.9(7) . . ?
C7 C14 C22 121.1(8) . . ?
C4 C16 O6 110.8(9) . . ?
C4 C16 C22 123.1(9) . . ?
C22 C16 O6 126.0(8) . . ?
N20 C17 C12 111.0(7) . . ?
O10 C19 O6 108.0(8) . . ?
C7 C21 C4 120.0(9) . . ?
C16 C22 C14 116.5(8) . . ?
C11 C1 C9 120.2(7) . . ?
C23 C1 C9 119.2(7) . . ?
C23 C1 C11 120.4(7) . . ?
O5 C3 C13 109.2(7) . . ?
C15 C3 O5 129.5(8) . . ?
C15 C3 C13 121.3(8) . . ?
C3 O5 C25 106.3(7) . . ?
C13 O8 C25 107.2(7) . . ?
C1 C9 C18 110.6(6) . . ?
C13 C11 C1 118.6(8) . . ?
O8 C13 C3 109.8(8) . . ?
C11 C13 C3 121.3(8) . . ?
C11 C13 O8 128.9(7) . . ?
C3 C15 C23 116.9(8) . . ?
N2 C18 C9 111.0(6) . . ?
C1 C23 C15 121.3(8) . . ?
O8 C25 O5 107.5(8) . . ?

_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.577
####################################################################### 
# 
# 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_mo_lyppb1019270k_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2106473'
loop_
_audit_author_name
_audit_author_address
'Zhenghuan Lin'
;Fujian Normal University
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 N O2, Br'
_chemical_formula_sum            'C9 H13 Br N O2'
_chemical_formula_weight         247.11
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   35.8606(14)
_cell_length_b                   4.54960(10)
_cell_length_c                   6.1929(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1010.38(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.037
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8812
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.477
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1432
_reflns_number_total             1749
_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    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         1.050
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+7.4359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51(6) 0.49(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 O5-C12
 1.322 with sigma of 0.01
 O10-C2
 1.416 with sigma of 0.01
 O10-C3AA
 1.272 with sigma of 0.01
 O5-C3AA
 1.612 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N29) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C2AA(H2Aa,H2Ab), C10(H10a,H10b)
5.b Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C3(H3), C11(H11)
5.c Idealised Me refined as rotating group:
 N29(H29a,H29b,H29c)
;
_atom_sites_solution_hydrogens   mixed
_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
O5 O -0.2179(5) 1.218(5) 0.567(3) 0.113(7) Uani 1 1 d D . . . .
O10 O -0.2140(4) 1.068(4) 0.932(2) 0.119(8) Uani 1 1 d D . . . .
N29 N -0.0329(2) 0.3973(19) -0.201(4) 0.032(2) Uani 1 1 d . U . . .
H29A H -0.0365 0.2638 -0.3038 0.039 Uiso 1 1 calc GR . . . .
H29B H -0.0305 0.3075 -0.0739 0.039 Uiso 1 1 calc GR . . . .
H29C H -0.0122 0.4988 -0.2292 0.039 Uiso 1 1 calc GR . . . .
C1AA C -0.1577(4) 0.719(4) 0.845(4) 0.075(8) Uani 1 1 d . . . . .
H1AA H -0.1562 0.6338 0.9809 0.090 Uiso 1 1 calc R . . . .
C2 C -0.1852(3) 0.920(3) 0.809(4) 0.035(3) Uani 1 1 d D . . . .
C0AA C -0.1325(4) 0.634(3) 0.693(2) 0.039(3) Uani 1 1 d . . . . .
C3 C -0.1639(5) 0.947(5) 0.423(3) 0.068(5) Uani 1 1 d . . . . .
H3 H -0.1653 1.0251 0.2845 0.081 Uiso 1 1 calc R . . . .
C2AA C -0.0650(3) 0.599(2) -0.194(4) 0.031(3) Uani 1 1 d . . . . .
H2AA H -0.0638 0.7356 -0.3138 0.037 Uiso 1 1 calc R . . . .
H2AB H -0.0645 0.7118 -0.0606 0.037 Uiso 1 1 calc R . . . .
C3AA C -0.2346(4) 1.215(4) 0.810(3) 0.052(4) Uani 1 1 d D . . . .
C10 C -0.1007(3) 0.424(3) 0.794(6) 0.087(8) Uani 1 1 d . . . . .
H10A H -0.1079 0.3593 0.9373 0.105 Uiso 1 1 calc R . . . .
H10B H -0.0971 0.2526 0.7038 0.105 Uiso 1 1 calc R . . . .
C11 C -0.1369(5) 0.749(5) 0.483(3) 0.063(5) Uani 1 1 d . . . . .
H11 H -0.1203 0.6856 0.3769 0.075 Uiso 1 1 calc R . . . .
C12 C -0.1910(6) 1.028(3) 0.598(3) 0.064(6) Uani 1 1 d D . . . .
Br1 Br -0.03754(3) 0.1159(2) 0.2886(7) 0.0361(4) Uani 1 1 d . . . . .
H3AA H -0.263(3) 1.16(2) 0.852(17) 0.02(3) Uiso 1 1 d . . . . .
H3AB H -0.239(4) 1.37(3) 0.85(3) 0.04(5) 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
O5 C3AA 1.618(13) . ?
O5 C12 1.309(13) . ?
O10 C2 1.448(13) . ?
O10 C3AA 1.252(12) . ?
N29 H29A 0.8900 . ?
N29 H29B 0.8900 . ?
N29 H29C 0.8900 . ?
N29 C2AA 1.476(13) . ?
C1AA H1AA 0.9300 . ?
C1AA C2 1.36(2) . ?
C1AA C0AA 1.36(2) . ?
C2 C12 1.41(3) . ?
C0AA C10 1.61(3) . ?
C0AA C11 1.41(2) . ?
C3 H3 0.9300 . ?
C3 C11 1.38(3) . ?
C3 C12 1.50(3) . ?
C2AA H2AA 0.9700 . ?
C2AA H2AB 0.9700 . ?
C2AA C10 1.506(16) 1_554 ?
C3AA H3AA 1.09(11) . ?
C3AA H3AB 0.78(14) . ?
C10 C2AA 1.506(16) 1_556 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O5 C3AA 97.6(14) . . ?
C3AA O10 C2 110.5(14) . . ?
H29A N29 H29B 109.5 . . ?
H29A N29 H29C 109.5 . . ?
H29B N29 H29C 109.5 . . ?
C2AA N29 H29A 109.5 . . ?
C2AA N29 H29B 109.5 . . ?
C2AA N29 H29C 109.5 . . ?
C2 C1AA H1AA 117.9 . . ?
C0AA C1AA H1AA 117.9 . . ?
C0AA C1AA C2 124(2) . . ?
C1AA C2 O10 138(2) . . ?
C1AA C2 C12 119.2(19) . . ?
C12 C2 O10 102.8(13) . . ?
C1AA C0AA C10 111.8(17) . . ?
C1AA C0AA C11 117.2(16) . . ?
C11 C0AA C10 130.9(17) . . ?
C11 C3 H3 122.5 . . ?
C11 C3 C12 115.1(15) . . ?
C12 C3 H3 122.5 . . ?
N29 C2AA H2AA 109.8 . . ?
N29 C2AA H2AB 109.8 . . ?
N29 C2AA C10 109.4(9) . 1_554 ?
H2AA C2AA H2AB 108.2 . . ?
C10 C2AA H2AA 109.8 1_554 . ?
C10 C2AA H2AB 109.8 1_554 . ?
O5 C3AA H3AA 125(6) . . ?
O5 C3AA H3AB 114(10) . . ?
O10 C3AA O5 110.4(14) . . ?
O10 C3AA H3AA 106(6) . . ?
O10 C3AA H3AB 113(10) . . ?
H3AA C3AA H3AB 87(10) . . ?
C0AA C10 H10A 110.1 . . ?
C0AA C10 H10B 110.1 . . ?
C2AA C10 C0AA 107.9(12) 1_556 . ?
C2AA C10 H10A 110.1 1_556 . ?
C2AA C10 H10B 110.1 1_556 . ?
H10A C10 H10B 108.4 . . ?
C0AA C11 H11 117.7 . . ?
C3 C11 C0AA 124.7(16) . . ?
C3 C11 H11 117.7 . . ?
O5 C12 C2 118.2(17) . . ?
O5 C12 C3 122.3(16) . . ?
C2 C12 C3 119.2(13) . . ?

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
O10 C2 C12 O5 1(2) . . . . ?
O10 C2 C12 C3 174.4(17) . . . . ?
C1AA C2 C12 O5 178.9(18) . . . . ?
C1AA C2 C12 C3 -7(2) . . . . ?
C1AA C0AA C10 C2AA -108(2) . . . 1_556 ?
C1AA C0AA C11 C3 2(3) . . . . ?
C2 O10 C3AA O5 -7(2) . . . . ?
C2 C1AA C0AA C10 172.7(14) . . . . ?
C2 C1AA C0AA C11 -4(2) . . . . ?
C0AA C1AA C2 O10 -175.4(16) . . . . ?
C0AA C1AA C2 C12 7(2) . . . . ?
C3AA O5 C12 C2 -4(2) . . . . ?
C3AA O5 C12 C3 -177.8(17) . . . . ?
C3AA O10 C2 C1AA -173.1(18) . . . . ?
C3AA O10 C2 C12 5(2) . . . . ?
C10 C0AA C11 C3 -174.0(18) . . . . ?
C11 C0AA C10 C2AA 69(3) . . . 1_556 ?
C11 C3 C12 O5 179(2) . . . . ?
C11 C3 C12 C2 5(3) . . . . ?
C12 O5 C3AA O10 7(2) . . . . ?
C12 C3 C11 C0AA -3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51(6)
2 0.49(6)

