# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelxt_a
_database_code_depnum_ccdc_archive 'CCDC 2178010'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        monoclinic
_chemical_formula_moiety         'C21 H26 Cl N O'
_chemical_formula_sum            'C21 H26 Cl N O'
_chemical_formula_weight         343.88
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.920(3)
_cell_length_b                   10.5010(14)
_cell_length_c                   10.4042(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.549(6)
_cell_angle_gamma                90
_cell_volume                     1955.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11167
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.96
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR(Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.249
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2675
_reflns_number_total             4455
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0883
_refine_ls_restrained_S_all      1.052
_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)+(0.1052P)²+1.8444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2257
_refine_ls_wR_factor_ref         0.2540
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C4 \\sim C00D \\sim C3 \\sim C00M: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C3A \\sim C00D \\sim C4A \\sim C00N: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C00D) = Uanis(C4) = Uanis(C3A) = Uanis(C3) = Uanis(C00N) = Uanis(C00M) =
Uanis(C4A)
3. Rigid body (RIGU) restrains
 C00M, C3, C4, C00D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3A, C4A, C00D, C00N
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=
 Sof(C00N)=Sof(H00R)=Sof(H00S)=Sof(H00T)=1-FVAR(1)
 Sof(C00M)=Sof(H00O)=Sof(H00P)=Sof(H00Q)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J),
 C00L(H00N)
5.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00I(H00D,H00H,H00I), C00K(H00K,H00L,H00M), C00M(H00O,
 H00P,H00Q), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C3A(H3AA,H3AB,H3AC), C4A(H4AA,
 H4AB,H4AC), C00N(H00R,H00S,H00T)
5.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
Cl00 Cl 0.63132(6) 0.94060(12) 0.78071(12) 0.0821(4) Uani 1 1 d . . . . .
O002 O 0.32152(14) 0.5104(2) 0.3447(3) 0.0605(7) Uani 1 1 d . . . . .
H002 H 0.355311 0.550661 0.381604 0.091 Uiso 1 1 calc GR . . . .
N003 N 0.38645(16) 0.7053(3) 0.4602(3) 0.0563(8) Uani 1 1 d . . . . .
C004 C 0.21194(17) 0.5478(3) 0.2098(3) 0.0432(7) Uani 1 1 d . . . . .
C005 C 0.26957(17) 0.5924(3) 0.2944(3) 0.0455(7) Uani 1 1 d . . . . .
C006 C 0.27414(18) 0.7226(3) 0.3259(3) 0.0486(8) Uani 1 1 d . . . . .
C007 C 0.16206(18) 0.7666(3) 0.1939(3) 0.0460(8) Uani 1 1 d . . . . .
C008 C 0.16053(18) 0.6369(3) 0.1633(3) 0.0464(8) Uani 1 1 d . . . . .
H008 H 0.122130 0.608348 0.107452 0.056 Uiso 1 1 calc R . . . .
C009 C 0.2201(2) 0.8066(3) 0.2752(3) 0.0524(9) Uani 1 1 d . . . . .
H009 H 0.223391 0.892338 0.297033 0.063 Uiso 1 1 calc R . . . .
C00A C 0.2061(2) 0.4062(3) 0.1720(3) 0.0501(8) Uani 1 1 d . . . . .
C00B C 0.44346(19) 0.7640(4) 0.5386(3) 0.0534(9) Uani 1 1 d . . . . .
C00C C 0.5589(2) 0.8717(4) 0.6868(4) 0.0583(9) Uani 1 1 d . . . . .
C00D C 0.1025(3) 0.8595(4) 0.1401(5) 0.0773(8) Uani 1 1 d . U . . .
C00E C 0.3344(2) 0.7727(4) 0.4086(4) 0.0570(9) Uani 1 1 d . . . . .
H00E H 0.335028 0.859829 0.424870 0.068 Uiso 1 1 calc R . . . .
C00F C 0.5134(2) 0.7085(4) 0.5449(4) 0.0643(10) Uani 1 1 d . . . . .
H00F H 0.521656 0.634318 0.498846 0.077 Uiso 1 1 calc R . . . .
C00G C 0.5715(2) 0.7617(4) 0.6189(4) 0.0649(10) Uani 1 1 d . . . . .
H00G H 0.618361 0.723594 0.622756 0.078 Uiso 1 1 calc R . . . .
C00H C 0.2754(2) 0.3658(4) 0.1005(4) 0.0676(11) Uani 1 1 d . . . . .
H00A H 0.277897 0.414024 0.022380 0.101 Uiso 1 1 calc GR . . . .
H00B H 0.272244 0.276737 0.080334 0.101 Uiso 1 1 calc GR . . . .
H00C H 0.319454 0.381532 0.154073 0.101 Uiso 1 1 calc GR . . . .
C00I C 0.1984(3) 0.3238(4) 0.2925(4) 0.0671(11) Uani 1 1 d . . . . .
H00D H 0.239984 0.339373 0.351770 0.101 Uiso 1 1 calc GR . . . .
H00H H 0.197615 0.235485 0.268562 0.101 Uiso 1 1 calc GR . . . .
H00I H 0.152780 0.344928 0.332583 0.101 Uiso 1 1 calc GR . . . .
C00J C 0.4900(2) 0.9269(5) 0.6829(4) 0.0762(13) Uani 1 1 d . . . . .
H00J H 0.481948 1.000861 0.729521 0.091 Uiso 1 1 calc R . . . .
C00K C 0.1376(2) 0.3799(4) 0.0809(4) 0.0703(11) Uani 1 1 d . . . . .
H00K H 0.093190 0.408767 0.120250 0.105 Uiso 1 1 calc GR . . . .
H00L H 0.133832 0.290152 0.064368 0.105 Uiso 1 1 calc GR . . . .
H00M H 0.143105 0.424476 0.001292 0.105 Uiso 1 1 calc GR . . . .
C00L C 0.4324(2) 0.8729(5) 0.6098(4) 0.0732(12) Uani 1 1 d . . . . .
H00N H 0.385339 0.910332 0.608398 0.088 Uiso 1 1 calc R . . . .
C00M C 0.0850(5) 0.9654(9) 0.2354(8) 0.0773(8) Uani 0.536(4) 1 d . U P A 1
H00O H 0.079355 0.929199 0.319145 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H00P H 0.039488 1.007281 0.207523 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H00Q H 0.125130 1.025967 0.239222 0.116 Uiso 0.536(4) 1 calc GR . P A 1
C3 C 0.1250(5) 0.9134(9) 0.0179(8) 0.0773(8) Uani 0.536(4) 1 d . U P A 1
H3A H 0.174672 0.947061 0.028301 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H3B H 0.091121 0.980369 -0.008175 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H3C H 0.123840 0.847993 -0.046692 0.116 Uiso 0.536(4) 1 calc GR . P A 1
C4 C 0.0251(5) 0.7884(8) 0.1165(9) 0.0773(8) Uani 0.536(4) 1 d . U P A 1
H4A H 0.028975 0.728579 0.047305 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H4B H -0.013173 0.849534 0.094474 0.116 Uiso 0.536(4) 1 calc GR . P A 1
H4C H 0.012699 0.744003 0.193289 0.116 Uiso 0.536(4) 1 calc GR . P A 1
C3A C 0.0687(6) 0.8186(9) 0.0129(9) 0.0773(8) Uani 0.464(4) 1 d . U P A 2
H3AA H 0.107591 0.795940 -0.043269 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H3AB H 0.039757 0.887300 -0.024450 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H3AC H 0.036878 0.746359 0.024759 0.116 Uiso 0.464(4) 1 calc GR . P A 2
C4A C 0.0530(6) 0.8946(11) 0.2400(10) 0.0773(8) Uani 0.464(4) 1 d . U P A 2
H4AA H 0.021383 0.823691 0.258482 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H4AB H 0.022726 0.965515 0.211594 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H4AC H 0.081892 0.917885 0.316264 0.116 Uiso 0.464(4) 1 calc GR . P A 2
C00N C 0.1457(6) 0.9855(9) 0.0938(10) 0.0773(8) Uani 0.464(4) 1 d . U P A 2
H00R H 0.156414 1.039831 0.166514 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H00S H 0.114815 1.030195 0.031096 0.116 Uiso 0.464(4) 1 calc GR . P A 2
H00T H 0.191614 0.961108 0.056419 0.116 Uiso 0.464(4) 1 calc GR . P A 2


_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
Cl00 C00C 1.746(4) . ?
O002 C005 1.356(4) . ?
N003 C00B 1.419(4) . ?
N003 C00E 1.271(4) . ?
C004 C005 1.407(4) . ?
C004 C008 1.385(4) . ?
C004 C00A 1.540(5) . ?
C005 C006 1.407(5) . ?
C006 C009 1.396(5) . ?
C006 C00E 1.449(5) . ?
C007 C008 1.399(5) . ?
C007 C009 1.376(5) . ?
C007 C00D 1.533(5) . ?
C00A C00H 1.536(5) . ?
C00A C00I 1.535(5) . ?
C00A C00K 1.542(5) . ?
C00B C00F 1.382(5) . ?
C00B C00L 1.382(5) . ?
C00C C00G 1.377(6) . ?
C00C C00J 1.364(6) . ?
C00D C00M 1.531(10) . ?
C00D C3 1.465(10) . ?
C00D C4 1.585(10) . ?
C00D C3A 1.494(10) . ?
C00D C4A 1.444(11) . ?
C00D C00N 1.617(12) . ?
C00F C00G 1.383(5) . ?
C00J C00L 1.377(6) . ?

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
C00E N003 C00B 119.8(3) . . ?
C005 C004 C00A 121.4(3) . . ?
C008 C004 C005 116.8(3) . . ?
C008 C004 C00A 121.7(3) . . ?
O002 C005 C004 120.1(3) . . ?
O002 C005 C006 119.7(3) . . ?
C006 C005 C004 120.2(3) . . ?
C005 C006 C00E 121.7(3) . . ?
C009 C006 C005 119.5(3) . . ?
C009 C006 C00E 118.7(3) . . ?
C008 C007 C00D 122.0(3) . . ?
C009 C007 C008 116.3(3) . . ?
C009 C007 C00D 121.7(3) . . ?
C004 C008 C007 124.9(3) . . ?
C007 C009 C006 122.2(3) . . ?
C004 C00A C00K 111.9(3) . . ?
C00H C00A C004 110.0(3) . . ?
C00H C00A C00K 107.0(3) . . ?
C00I C00A C004 110.1(3) . . ?
C00I C00A C00H 110.1(3) . . ?
C00I C00A C00K 107.7(3) . . ?
C00F C00B N003 118.2(3) . . ?
C00F C00B C00L 118.3(3) . . ?
C00L C00B N003 123.4(3) . . ?
C00G C00C Cl00 120.1(3) . . ?
C00J C00C Cl00 119.3(3) . . ?
C00J C00C C00G 120.7(3) . . ?
C007 C00D C4 110.3(4) . . ?
C007 C00D C00N 107.1(4) . . ?
C00M C00D C007 112.6(4) . . ?
C00M C00D C4 103.9(6) . . ?
C3 C00D C007 110.4(4) . . ?
C3 C00D C00M 110.7(6) . . ?
C3 C00D C4 108.6(6) . . ?
C3A C00D C007 112.9(5) . . ?
C3A C00D C00N 98.8(6) . . ?
C4A C00D C007 109.9(5) . . ?
C4A C00D C3A 118.2(7) . . ?
C4A C00D C00N 108.9(7) . . ?
N003 C00E C006 124.2(3) . . ?
C00B C00F C00G 121.0(4) . . ?
C00C C00G C00F 119.2(3) . . ?
C00C C00J C00L 119.8(4) . . ?
C00J C00L C00B 121.0(4) . . ?

_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2178011'
loop_
_audit_author_name
_audit_author_address
'Shodai Hasebe'
;Waseda University
Japan
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        monoclinic
_chemical_formula_moiety         'C21 H26 Br N O'
_chemical_formula_sum            'C21 H26 Br N O'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.059(5)
_cell_length_b                   10.608(3)
_cell_length_c                   10.374(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.824(7)
_cell_angle_gamma                90
_cell_volume                     1984.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8286
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.92
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.324
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_T_max  0.8409
_exptl_absorpt_correction_T_min  0.4814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR(Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_unetI/netI     0.1166
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17870
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.258
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2192
_reflns_number_total             4469
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      1.009
_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)+(0.1019P)²+0.1971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.2123
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C008-C00C \\sim C008-C0AA
 with sigma of 0.02
 C00C-C00M \\sim C0AA-C00N
 with sigma of 0.02
 C00C-C10 \\sim C0AA-C10A
 with sigma of 0.02
 C00C-C12 \\sim C0AA-C12A
 with sigma of 0.02
 C008-C00M \\sim C008-C00N
 with sigma of 0.04
 C008-C10 \\sim C008-C10A
 with sigma of 0.04
 C008-C12 \\sim C008-C12A
 with sigma of 0.04
 C00M-C10 \\sim C00N-C10A
 with sigma of 0.04
 C00M-C12 \\sim C00N-C12A
 with sigma of 0.04
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C10 \\sim C12 \\sim C00C \\sim C00M: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C10A \\sim C00N \\sim C0AA \\sim C12A: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Others
 Sof(C0AA)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C00N)=Sof(H00S)=
 Sof(H00T)=Sof(H00U)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C00C)=Sof(C00M)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=Sof(C10)=Sof(H10A)=
 Sof(H10B)=Sof(H10C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00N),
 C00L(H00O)
5.b Idealised Me refined as rotating group:
 C00H(H00B,H00C,H00D), C00I(H00H,H00I,H00J), C00J(H00K,H00L,H00M), C00M(H00P,
 H00Q,H00R), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C10A(H10D,H10E,H10F),
 C00N(H00S,H00T,H00U), C12A(H12D,H12E,H12F)
5.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.36552(3) 0.94521(6) 0.21059(6) 0.0846(3) Uani 1 1 d . . . . .
O002 O 0.68007(19) 0.5115(3) 0.6563(4) 0.0668(9) Uani 1 1 d . . . . .
H002 H 0.647451 0.551020 0.616122 0.100 Uiso 1 1 calc GR . . . .
N003 N 0.6162(2) 0.7046(4) 0.5398(4) 0.0648(11) Uani 1 1 d . . . . .
C004 C 0.7320(3) 0.5932(4) 0.7067(5) 0.0526(11) Uani 1 1 d . . . . .
C005 C 0.7893(3) 0.5491(4) 0.7911(5) 0.0545(11) Uani 1 1 d . . . . .
C006 C 0.4439(3) 0.8700(5) 0.3121(5) 0.0623(13) Uani 1 1 d . . . . .
C007 C 0.7283(3) 0.7211(4) 0.6738(5) 0.0573(12) Uani 1 1 d . . . . .
C008 C 0.8402(3) 0.7646(4) 0.8054(4) 0.0532(11) Uani 1 1 d D . . . .
C009 C 0.8409(3) 0.6373(4) 0.8365(5) 0.0566(12) Uani 1 1 d . . . . .
H009 H 0.879100 0.608856 0.892481 0.068 Uiso 1 1 calc R . . . .
C00A C 0.7829(3) 0.8041(4) 0.7229(5) 0.0601(13) Uani 1 1 d . . . . .
H00A H 0.780358 0.888531 0.698960 0.072 Uiso 1 1 calc R . . . .
C00B C 0.7952(3) 0.4079(4) 0.8316(5) 0.0589(12) Uani 1 1 d . . . . .
C00C C 0.9020(7) 0.8543(11) 0.8573(12) 0.056(7) Uani 0.60(2) 1 d D U P A 1
C00D C 0.5592(3) 0.7627(5) 0.4606(5) 0.0603(12) Uani 1 1 d . . . . .
C00E C 0.6691(3) 0.7712(5) 0.5887(5) 0.0663(14) Uani 1 1 d . . . . .
H00E H 0.669845 0.856643 0.568915 0.080 Uiso 1 1 calc R . . . .
C00F C 0.4319(3) 0.7610(5) 0.3794(6) 0.0757(15) Uani 1 1 d . . . . .
H00F H 0.385406 0.723206 0.375471 0.091 Uiso 1 1 calc R . . . .
C00G C 0.4897(3) 0.7080(5) 0.4533(6) 0.0756(16) Uani 1 1 d . . . . .
H00G H 0.481674 0.634170 0.498884 0.091 Uiso 1 1 calc R . . . .
C00H C 0.8014(4) 0.3255(5) 0.7099(5) 0.0747(16) Uani 1 1 d . . . . .
H00B H 0.758863 0.339451 0.652347 0.112 Uiso 1 1 calc GR . . . .
H00C H 0.803538 0.238283 0.734285 0.112 Uiso 1 1 calc GR . . . .
H00D H 0.845535 0.347684 0.667247 0.112 Uiso 1 1 calc GR . . . .
C00I C 0.7263(3) 0.3708(5) 0.9035(5) 0.0745(15) Uani 1 1 d . . . . .
H00H H 0.723012 0.422685 0.978783 0.112 Uiso 1 1 calc GR . . . .
H00I H 0.730010 0.283904 0.928888 0.112 Uiso 1 1 calc GR . . . .
H00J H 0.682819 0.382520 0.847801 0.112 Uiso 1 1 calc GR . . . .
C00J C 0.8631(3) 0.3814(5) 0.9206(6) 0.0828(17) Uani 1 1 d . . . . .
H00K H 0.906967 0.407380 0.879130 0.124 Uiso 1 1 calc GR . . . .
H00L H 0.865879 0.292827 0.938943 0.124 Uiso 1 1 calc GR . . . .
H00M H 0.859215 0.427454 0.999617 0.124 Uiso 1 1 calc GR . . . .
C00K C 0.5129(4) 0.9248(6) 0.3175(6) 0.0877(19) Uani 1 1 d . . . . .
H00N H 0.520999 0.998430 0.271703 0.105 Uiso 1 1 calc R . . . .
C00L C 0.5699(3) 0.8712(6) 0.3902(6) 0.0845(18) Uani 1 1 d . . . . .
H00O H 0.616543 0.908436 0.392310 0.101 Uiso 1 1 calc R . . . .
C00M C 0.9173(11) 0.9564(16) 0.7620(16) 0.110(7) Uani 0.60(2) 1 d D U P A 1
H00P H 0.922606 0.919777 0.678326 0.165 Uiso 0.60(2) 1 calc GR . P A 1
H00Q H 0.962244 0.999427 0.788744 0.165 Uiso 0.60(2) 1 calc GR . P A 1
H00R H 0.876891 1.015275 0.757966 0.165 Uiso 0.60(2) 1 calc GR . P A 1
C10 C 0.8792(11) 0.911(2) 0.9800(16) 0.149(12) Uani 0.60(2) 1 d D U P A 1
H10A H 0.840747 0.972133 0.961836 0.223 Uiso 0.60(2) 1 calc GR . P A 1
H10B H 0.921059 0.952002 1.022699 0.223 Uiso 0.60(2) 1 calc GR . P A 1
H10C H 0.861044 0.846448 1.034806 0.223 Uiso 0.60(2) 1 calc GR . P A 1
C12 C 0.9759(8) 0.7851(12) 0.884(3) 0.131(9) Uani 0.60(2) 1 d D U P A 1
H12A H 0.972085 0.731111 0.957716 0.197 Uiso 0.60(2) 1 calc GR . P A 1
H12B H 1.014689 0.845600 0.901009 0.197 Uiso 0.60(2) 1 calc GR . P A 1
H12C H 0.987068 0.735346 0.810212 0.197 Uiso 0.60(2) 1 calc GR . P A 1
C0AA C 0.8953(10) 0.8639(16) 0.8632(19) 0.072(13) Uani 0.40(2) 1 d D U P A 2
C10A C 0.8572(12) 0.984(2) 0.894(4) 0.135(13) Uani 0.40(2) 1 d D U P A 2
H10D H 0.833343 1.017372 0.816481 0.202 Uiso 0.40(2) 1 calc GR . P A 2
H10E H 0.892904 1.043251 0.928412 0.202 Uiso 0.40(2) 1 calc GR . P A 2
H10F H 0.820752 0.967797 0.956066 0.202 Uiso 0.40(2) 1 calc GR . P A 2
C00N C 0.9531(14) 0.886(3) 0.767(3) 0.134(14) Uani 0.40(2) 1 d D U P A 2
H00S H 0.985420 0.813832 0.765290 0.201 Uiso 0.40(2) 1 calc GR . P A 2
H00T H 0.981411 0.959311 0.790611 0.201 Uiso 0.40(2) 1 calc GR . P A 2
H00U H 0.929474 0.897556 0.682746 0.201 Uiso 0.40(2) 1 calc GR . P A 2
C12A C 0.9342(15) 0.815(2) 0.988(2) 0.106(10) Uani 0.40(2) 1 d D U P A 2
H12D H 0.900408 0.817439 1.056445 0.160 Uiso 0.40(2) 1 calc GR . P A 2
H12E H 0.976500 0.866624 1.010028 0.160 Uiso 0.40(2) 1 calc GR . P A 2
H12F H 0.950067 0.729457 0.975338 0.160 Uiso 0.40(2) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C006 1.897(5) . ?
O002 C004 1.362(5) . ?
N003 C00D 1.425(6) . ?
N003 C00E 1.273(7) . ?
C004 C005 1.403(7) . ?
C004 C007 1.400(6) . ?
C005 C009 1.387(6) . ?
C005 C00B 1.558(6) . ?
C006 C00F 1.374(7) . ?
C006 C00K 1.375(7) . ?
C007 C00A 1.399(6) . ?
C007 C00E 1.452(7) . ?
C008 C009 1.388(6) . ?
C008 C00A 1.376(6) . ?
C008 C00C 1.544(10) . ?
C008 C0AA 1.549(13) . ?
C00B C00H 1.544(7) . ?
C00B C00I 1.533(7) . ?
C00B C00J 1.524(8) . ?
C00C C00M 1.501(13) . ?
C00C C10 1.485(15) . ?
C00C C12 1.537(16) . ?
C00D C00G 1.380(7) . ?
C00D C00L 1.382(7) . ?
C00F C00G 1.384(7) . ?
C00K C00L 1.368(8) . ?
C0AA C10A 1.486(18) . ?
C0AA C00N 1.498(17) . ?
C0AA C12A 1.533(19) . ?

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
C00E N003 C00D 119.8(4) . . ?
O002 C004 C005 120.0(4) . . ?
O002 C004 C007 120.0(4) . . ?
C007 C004 C005 120.1(4) . . ?
C004 C005 C00B 121.9(4) . . ?
C009 C005 C004 116.7(4) . . ?
C009 C005 C00B 121.4(5) . . ?
C00F C006 Br01 120.3(4) . . ?
C00F C006 C00K 120.0(5) . . ?
C00K C006 Br01 119.7(4) . . ?
C004 C007 C00E 121.8(4) . . ?
C00A C007 C004 119.7(5) . . ?
C00A C007 C00E 118.4(4) . . ?
C009 C008 C00C 121.4(6) . . ?
C009 C008 C0AA 125.0(9) . . ?
C00A C008 C009 116.1(4) . . ?
C00A C008 C00C 122.5(6) . . ?
C00A C008 C0AA 118.9(8) . . ?
C005 C009 C008 125.4(5) . . ?
C008 C00A C007 122.0(4) . . ?
C00H C00B C005 109.3(4) . . ?
C00I C00B C005 109.4(4) . . ?
C00I C00B C00H 110.2(4) . . ?
C00J C00B C005 112.5(4) . . ?
C00J C00B C00H 107.6(4) . . ?
C00J C00B C00I 107.8(4) . . ?
C00M C00C C008 111.6(9) . . ?
C00M C00C C12 106.1(12) . . ?
C10 C00C C008 108.9(10) . . ?
C10 C00C C00M 109.8(13) . . ?
C10 C00C C12 108.3(12) . . ?
C12 C00C C008 112.0(9) . . ?
C00G C00D N003 118.6(5) . . ?
C00G C00D C00L 118.1(5) . . ?
C00L C00D N003 123.3(5) . . ?
N003 C00E C007 123.7(5) . . ?
C006 C00F C00G 119.4(5) . . ?
C00D C00G C00F 121.2(5) . . ?
C00L C00K C006 120.2(5) . . ?
C00K C00L C00D 121.1(5) . . ?
C10A C0AA C008 111.6(13) . . ?
C10A C0AA C00N 110.8(18) . . ?
C10A C0AA C12A 108.0(17) . . ?
C00N C0AA C008 107.6(14) . . ?
C00N C0AA C12A 108.0(17) . . ?
C12A C0AA C008 110.8(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'



