# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2032905'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.064(3)
_cell_length_b                   23.992(9)
_cell_length_c                   9.994(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.766(4)
_cell_angle_gamma                90
_cell_volume                     1674.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2939
_cell_measurement_theta_min      2.2299
_cell_measurement_theta_max      26.5236

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10867
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2936
_reflns_number_gt                2035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.5975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2936
_refine_ls_number_parameters     219
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2950(3) 0.05240(7) 0.51377(19) 0.0656(5) Uani 1 1 d . . . . .
O2 O 0.5421(2) 0.31193(6) 0.29685(15) 0.0502(4) Uani 1 1 d . . . . .
H2 H 0.601600 0.282567 0.309264 0.075 Uiso 1 1 calc R U . . .
N1 N 0.7629(2) 0.23340(7) 0.42924(17) 0.0384(4) Uani 1 1 d . . . . .
C1 C 0.1556(4) 0.05818(12) 0.6016(3) 0.0799(9) Uani 1 1 d . . . . .
H1A H 0.216464 0.071081 0.688552 0.120 Uiso 1 1 calc R U . . .
H1B H 0.096172 0.022752 0.611696 0.120 Uiso 1 1 calc R U . . .
H1C H 0.060066 0.084598 0.563924 0.120 Uiso 1 1 calc R U . . .
C2 C 0.4034(3) 0.09886(9) 0.4963(2) 0.0449(6) Uani 1 1 d . . . . .
C3 C 0.5453(3) 0.09178(9) 0.4165(3) 0.0531(6) Uani 1 1 d . . . . .
H3 H 0.561061 0.057184 0.377678 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6640(3) 0.13543(9) 0.3937(2) 0.0472(6) Uani 1 1 d . . . . .
H4 H 0.757919 0.130053 0.339091 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6440(3) 0.18753(8) 0.4521(2) 0.0353(5) Uani 1 1 d . . . . .
C6 C 0.4984(3) 0.19423(9) 0.5291(2) 0.0399(5) Uani 1 1 d . . . . .
H6 H 0.479731 0.228950 0.566313 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3794(3) 0.15023(9) 0.5519(2) 0.0434(6) Uani 1 1 d . . . . .
H7 H 0.283469 0.155590 0.604830 0.052 Uiso 1 1 calc R U . . .
C8 C 0.9370(3) 0.22217(10) 0.3688(2) 0.0492(6) Uani 1 1 d . . . . .
H8A H 0.905243 0.213781 0.273061 0.059 Uiso 1 1 calc R U . . .
H8B H 1.008997 0.191292 0.413939 0.059 Uiso 1 1 calc R U . . .
C9 C 1.0481(3) 0.27583(11) 0.3910(3) 0.0573(7) Uani 1 1 d . U . . .
H9A H 0.998164 0.303758 0.324754 0.069 Uiso 1 1 calc R U . . .
H9B H 1.182947 0.269967 0.386889 0.069 Uiso 1 1 calc R U . . .
C10 C 1.0168(3) 0.29249(11) 0.5314(3) 0.0575(7) Uani 1 1 d . . . . .
H10A H 1.032754 0.332379 0.544243 0.069 Uiso 1 1 calc R U . . .
H10B H 1.106314 0.273393 0.599393 0.069 Uiso 1 1 calc R U . . .
C11 C 0.8084(3) 0.27487(9) 0.5405(2) 0.0404(5) Uani 1 1 d . . . . .
H11 H 0.802695 0.256791 0.626678 0.048 Uiso 1 1 d R U . . .
C12 C 0.6691(3) 0.32341(8) 0.5318(2) 0.0355(5) Uani 1 1 d . . . . .
C13 C 0.5495(3) 0.33945(8) 0.4168(2) 0.0358(5) Uani 1 1 d . . . . .
C14 C 0.4264(3) 0.38670(8) 0.4157(2) 0.0390(5) Uani 1 1 d . . . . .
C15 C 0.3052(3) 0.40394(9) 0.2981(3) 0.0492(6) Uani 1 1 d . . . . .
H15 H 0.300453 0.383327 0.218820 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1943(3) 0.45056(10) 0.2988(3) 0.0626(7) Uani 1 1 d . . . . .
H16 H 0.117108 0.461882 0.219651 0.075 Uiso 1 1 calc R U . . .
C17 C 0.1961(4) 0.48113(11) 0.4169(3) 0.0678(8) Uani 1 1 d . . . . .
H17 H 0.120411 0.512851 0.416594 0.081 Uiso 1 1 calc R U . . .
C18 C 0.3080(4) 0.46487(10) 0.5326(3) 0.0614(7) Uani 1 1 d . . . . .
H18 H 0.306129 0.485395 0.611364 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4279(3) 0.41728(9) 0.5366(2) 0.0447(6) Uani 1 1 d . . . . .
C20 C 0.5528(4) 0.40058(10) 0.6541(2) 0.0526(6) Uani 1 1 d . . . . .
H20 H 0.556665 0.420773 0.733939 0.063 Uiso 1 1 calc R U . . .
C21 C 0.6673(3) 0.35507(9) 0.6510(2) 0.0463(6) Uani 1 1 d . . . . .
H21 H 0.746961 0.344491 0.729692 0.056 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.378(3) . ?
O1 C1 1.422(3) . ?
O2 C13 1.362(2) . ?
O2 H2 0.8200 . ?
N1 C5 1.424(3) . ?
N1 C8 1.475(3) . ?
N1 C11 1.490(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.373(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.506(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.507(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.547(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.519(3) . ?
C11 H11 0.9705 . ?
C12 C13 1.374(3) . ?
C12 C21 1.414(3) . ?
C13 C14 1.428(3) . ?
C14 C15 1.407(3) . ?
C14 C19 1.412(3) . ?
C15 C16 1.366(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.419(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.415(3) . ?
C20 C21 1.362(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C2 O1 C1 116.7(2) . . ?
C13 O2 H2 109.5 . . ?
C5 N1 C8 118.26(17) . . ?
C5 N1 C11 117.50(17) . . ?
C8 N1 C11 109.20(16) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 124.7(2) . . ?
C7 C2 C3 119.2(2) . . ?
O1 C2 C3 116.1(2) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 117.87(19) . . ?
C6 C5 N1 120.39(18) . . ?
C4 C5 N1 121.68(19) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 120.0(2) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C9 103.39(19) . . ?
N1 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
N1 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.0 . . ?
C8 C9 C10 102.5(2) . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C10 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C9 C10 C11 104.98(19) . . ?
C9 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
N1 C11 C12 113.89(16) . . ?
N1 C11 C10 103.73(18) . . ?
C12 C11 C10 113.65(18) . . ?
N1 C11 H11 109.3 . . ?
C12 C11 H11 106.2 . . ?
C10 C11 H11 110.1 . . ?
C13 C12 C21 118.1(2) . . ?
C13 C12 C11 124.95(19) . . ?
C21 C12 C11 116.90(18) . . ?
O2 C13 C12 122.47(18) . . ?
O2 C13 C14 115.90(18) . . ?
C12 C13 C14 121.63(19) . . ?
C15 C14 C19 119.1(2) . . ?
C15 C14 C13 122.1(2) . . ?
C19 C14 C13 118.8(2) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C20 119.0(2) . . ?
C14 C19 C18 117.9(2) . . ?
C20 C19 C18 123.0(2) . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C12 122.1(2) . . ?
C20 C21 H21 118.9 . . ?
C12 C21 H21 118.9 . . ?

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
C1 O1 C2 C7 -3.4(3) . . . . ?
C1 O1 C2 C3 176.6(2) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
O1 C2 C3 C4 -179.2(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C5 N1 -179.3(2) . . . . ?
C8 N1 C5 C6 168.88(18) . . . . ?
C11 N1 C5 C6 34.4(3) . . . . ?
C8 N1 C5 C4 -14.0(3) . . . . ?
C11 N1 C5 C4 -148.46(19) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
N1 C5 C6 C7 179.45(18) . . . . ?
O1 C2 C7 C6 179.2(2) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 N1 C8 C9 -166.73(18) . . . . ?
C11 N1 C8 C9 -28.8(2) . . . . ?
N1 C8 C9 C10 39.8(2) . . . . ?
C8 C9 C10 C11 -36.4(2) . . . . ?
C5 N1 C11 C12 -91.5(2) . . . . ?
C8 N1 C11 C12 130.16(18) . . . . ?
C5 N1 C11 C10 144.40(18) . . . . ?
C8 N1 C11 C10 6.1(2) . . . . ?
C9 C10 C11 N1 19.0(2) . . . . ?
C9 C10 C11 C12 -105.2(2) . . . . ?
N1 C11 C12 C13 -19.8(3) . . . . ?
C10 C11 C12 C13 98.7(2) . . . . ?
N1 C11 C12 C21 161.94(18) . . . . ?
C10 C11 C12 C21 -79.5(2) . . . . ?
C21 C12 C13 O2 179.41(19) . . . . ?
C11 C12 C13 O2 1.2(3) . . . . ?
C21 C12 C13 C14 0.1(3) . . . . ?
C11 C12 C13 C14 -178.06(18) . . . . ?
O2 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 179.2(2) . . . . ?
O2 C13 C14 C19 -179.64(18) . . . . ?
C12 C13 C14 C19 -0.3(3) . . . . ?
C19 C14 C15 C16 2.0(3) . . . . ?
C13 C14 C15 C16 -177.5(2) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C15 C14 C19 C20 -178.7(2) . . . . ?
C13 C14 C19 C20 0.8(3) . . . . ?
C15 C14 C19 C18 -1.0(3) . . . . ?
C13 C14 C19 C18 178.52(19) . . . . ?
C17 C18 C19 C14 -0.5(4) . . . . ?
C17 C18 C19 C20 177.1(2) . . . . ?
C14 C19 C20 C21 -1.1(3) . . . . ?
C18 C19 C20 C21 -178.7(2) . . . . ?
C19 C20 C21 C12 0.9(3) . . . . ?
C13 C12 C21 C20 -0.4(3) . . . . ?
C11 C12 C21 C20 177.9(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 2032906'
loop_
_audit_author_name
_audit_author_address
'Ruwei Shen'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-09-21 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 Br N O2'
_chemical_formula_sum            'C21 H20 Br N O2'
_chemical_formula_weight         398.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.5488(8)
_cell_length_b                   14.1447(14)
_cell_length_c                   17.0775(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1823.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4880
_cell_measurement_theta_min      2.7864
_cell_measurement_theta_max      23.7018

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13075
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_full        25.002
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3193
_reflns_number_gt                2818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0106P)²+0.4357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.017(11)
_chemical_absolute_configuration S
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19192(6) 0.09607(3) 0.33173(3) 0.06720(17) Uani 1 1 d . . . . .
O1 O 0.1670(3) 0.88603(18) 0.27307(16) 0.0552(7) Uani 1 1 d . . . . .
O2 O 0.4378(4) 0.5945(2) 0.55782(15) 0.0579(7) Uani 1 1 d . . . . .
H2 H 0.509223 0.621460 0.529322 0.087 Uiso 1 1 calc R U . . .
N1 N 0.6166(4) 0.6323(2) 0.42662(18) 0.0414(7) Uani 1 1 d . . . . .
C1 C 0.0003(7) 0.8576(4) 0.2430(3) 0.0774(15) Uani 1 1 d . . . . .
H1A H 0.017575 0.811640 0.202316 0.116 Uiso 1 1 calc R U . . .
H1B H -0.060409 0.911583 0.221967 0.116 Uiso 1 1 calc R U . . .
H1C H -0.069294 0.830304 0.284251 0.116 Uiso 1 1 calc R U . . .
C2 C 0.2668(5) 0.8191(3) 0.3115(2) 0.0433(9) Uani 1 1 d . . . . .
C3 C 0.4146(5) 0.8520(3) 0.3492(2) 0.0468(10) Uani 1 1 d . . . . .
H3 H 0.438164 0.916501 0.349711 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5286(5) 0.7908(3) 0.3862(2) 0.0440(9) Uani 1 1 d . . . . .
H4 H 0.627809 0.814794 0.411672 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4986(5) 0.6934(3) 0.3863(2) 0.0406(9) Uani 1 1 d . . . . .
C6 C 0.3473(5) 0.6614(3) 0.3491(2) 0.0483(10) Uani 1 1 d . . . . .
H6 H 0.322244 0.597051 0.349044 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2320(5) 0.7234(3) 0.3119(2) 0.0502(11) Uani 1 1 d . . . . .
H7 H 0.131111 0.700222 0.287250 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8067(6) 0.6596(3) 0.4255(3) 0.0597(11) Uani 1 1 d . . . . .
H8A H 0.837351 0.693814 0.472762 0.072 Uiso 1 1 calc R U . . .
H8B H 0.831551 0.699582 0.380660 0.072 Uiso 1 1 calc R U . . .
C9 C 0.9112(6) 0.5690(3) 0.4203(4) 0.0853(17) Uani 1 1 d . . . . .
H9A H 0.959797 0.560967 0.368122 0.102 Uiso 1 1 calc R U . . .
H9B H 1.007880 0.569311 0.457708 0.102 Uiso 1 1 calc R U . . .
C10 C 0.7847(5) 0.4927(3) 0.4384(3) 0.0615(12) Uani 1 1 d . . . . .
H10A H 0.783226 0.479795 0.494201 0.074 Uiso 1 1 calc R U . . .
H10B H 0.816426 0.435223 0.410847 0.074 Uiso 1 1 calc R U . . .
C11 C 0.6031(5) 0.5290(3) 0.4110(2) 0.0417(9) Uani 1 1 d . . . . .
H11 H 0.590372 0.517308 0.355554 0.050 Uiso 1 1 d R U . . .
C12 C 0.4530(4) 0.4799(2) 0.4540(2) 0.0367(8) Uani 1 1 d . . . . .
C13 C 0.3850(5) 0.5130(3) 0.5236(2) 0.0433(9) Uani 1 1 d . . . . .
C14 C 0.2555(5) 0.4613(3) 0.5647(3) 0.0552(11) Uani 1 1 d . . . . .
H14 H 0.211270 0.484931 0.611573 0.066 Uiso 1 1 calc R U . . .
C15 C 0.1943(5) 0.3780(3) 0.5371(2) 0.0545(10) Uani 1 1 d . . . . .
H15 H 0.108577 0.345382 0.565344 0.065 Uiso 1 1 calc R U . . .
C16 C 0.2578(4) 0.3396(3) 0.4664(2) 0.0423(9) Uani 1 1 d . . . . .
C17 C 0.1996(5) 0.2511(3) 0.4377(2) 0.0495(10) Uani 1 1 d . . . . .
H17 H 0.114381 0.217122 0.465130 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2671(5) 0.2156(3) 0.3705(2) 0.0454(9) Uani 1 1 d . . . . .
C19 C 0.3947(5) 0.2646(2) 0.3280(3) 0.0450(8) Uani 1 1 d . . . . .
H19 H 0.439685 0.239061 0.281944 0.054 Uiso 1 1 calc R U . . .
C20 C 0.4537(5) 0.3498(2) 0.3541(2) 0.0407(9) Uani 1 1 d . . . . .
H20 H 0.538685 0.382012 0.325015 0.049 Uiso 1 1 calc R U . . .
C21 C 0.3892(4) 0.3913(2) 0.4244(2) 0.0363(8) 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 C18 1.903(4) . ?
O1 C2 1.376(4) . ?
O1 C1 1.418(5) . ?
O2 C13 1.353(5) . ?
O2 H2 0.8200 . ?
N1 C5 1.420(5) . ?
N1 C8 1.486(5) . ?
N1 C11 1.489(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.369(5) . ?
C2 C7 1.380(5) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C6 C7 1.389(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.506(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.474(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.537(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(5) . ?
C11 H11 0.9658 . ?
C12 C13 1.376(5) . ?
C12 C21 1.436(5) . ?
C13 C14 1.408(5) . ?
C14 C15 1.350(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.414(5) . ?
C16 C21 1.426(5) . ?
C17 C18 1.352(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(5) . ?
C19 C20 1.360(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.422(5) . ?
C20 H20 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
C2 O1 C1 117.6(3) . . ?
C13 O2 H2 109.5 . . ?
C5 N1 C8 116.2(3) . . ?
C5 N1 C11 117.9(3) . . ?
C8 N1 C11 108.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 115.9(3) . . ?
C3 C2 C7 119.0(4) . . ?
O1 C2 C7 125.0(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.2(4) . . ?
C6 C5 N1 122.8(3) . . ?
C4 C5 N1 120.0(3) . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C9 106.6(3) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C10 C9 C8 105.7(4) . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
C9 C10 C11 105.6(3) . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
N1 C11 C12 114.4(3) . . ?
N1 C11 C10 102.2(3) . . ?
C12 C11 C10 111.4(3) . . ?
N1 C11 H11 110.5 . . ?
C12 C11 H11 108.8 . . ?
C10 C11 H11 109.3 . . ?
C13 C12 C21 118.4(3) . . ?
C13 C12 C11 122.8(3) . . ?
C21 C12 C11 118.6(3) . . ?
O2 C13 C12 123.5(3) . . ?
O2 C13 C14 115.6(3) . . ?
C12 C13 C14 120.8(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 122.3(3) . . ?
C15 C16 C21 118.0(4) . . ?
C17 C16 C21 119.7(4) . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 Br1 120.8(3) . . ?
C19 C18 Br1 117.9(3) . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 122.0(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C16 116.9(3) . . ?
C20 C21 C12 122.9(3) . . ?
C16 C21 C12 120.3(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
C1 O1 C2 C3 -171.1(4) . . . . ?
C1 O1 C2 C7 11.3(6) . . . . ?
O1 C2 C3 C4 -176.8(3) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C4 C5 N1 -178.5(3) . . . . ?
C8 N1 C5 C6 147.6(4) . . . . ?
C11 N1 C5 C6 16.2(5) . . . . ?
C8 N1 C5 C4 -35.4(5) . . . . ?
C11 N1 C5 C4 -166.8(3) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
N1 C5 C6 C7 178.3(4) . . . . ?
C3 C2 C7 C6 -1.0(6) . . . . ?
O1 C2 C7 C6 176.4(4) . . . . ?
C5 C6 C7 C2 0.0(6) . . . . ?
C5 N1 C8 C9 -143.6(4) . . . . ?
C11 N1 C8 C9 -7.9(5) . . . . ?
N1 C8 C9 C10 -13.8(6) . . . . ?
C8 C9 C10 C11 29.6(6) . . . . ?
C5 N1 C11 C12 -79.4(4) . . . . ?
C8 N1 C11 C12 145.8(3) . . . . ?
C5 N1 C11 C10 160.0(3) . . . . ?
C8 N1 C11 C10 25.2(4) . . . . ?
C9 C10 C11 N1 -33.8(5) . . . . ?
C9 C10 C11 C12 -156.4(4) . . . . ?
N1 C11 C12 C13 -26.4(5) . . . . ?
C10 C11 C12 C13 88.9(4) . . . . ?
N1 C11 C12 C21 158.9(3) . . . . ?
C10 C11 C12 C21 -85.8(4) . . . . ?
C21 C12 C13 O2 178.6(3) . . . . ?
C11 C12 C13 O2 3.9(5) . . . . ?
C21 C12 C13 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 -175.0(3) . . . . ?
O2 C13 C14 C15 -178.9(4) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C17 178.0(4) . . . . ?
C14 C15 C16 C21 0.0(6) . . . . ?
C15 C16 C17 C18 -178.4(4) . . . . ?
C21 C16 C17 C18 -0.3(5) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C16 C17 C18 Br1 179.3(3) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
Br1 C18 C19 C20 -179.3(3) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C20 C21 C16 -0.6(5) . . . . ?
C19 C20 C21 C12 178.3(3) . . . . ?
C15 C16 C21 C20 178.7(3) . . . . ?
C17 C16 C21 C20 0.6(5) . . . . ?
C15 C16 C21 C12 -0.2(5) . . . . ?
C17 C16 C21 C12 -178.3(3) . . . . ?
C13 C12 C21 C20 -178.5(3) . . . . ?
C11 C12 C21 C20 -3.6(5) . . . . ?
C13 C12 C21 C16 0.3(5) . . . . ?
C11 C12 C21 C16 175.3(3) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.041



