# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mx8972
_database_code_depnum_ccdc_archive 'CCDC 2048302'
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2020-12-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O2'
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.04690(10)
_cell_length_b                   10.3794(2)
_cell_length_c                   16.3300(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1702.91(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30427
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.9420
_cell_measurement_theta_min      2.2940
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42107
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.886
_diffrn_reflns_theta_min         2.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    2.00    --    5.00  45.00  90.00  356
  2  ω    -19.00  48.00   0.50    2.00    --    5.00  45.00  60.00  134
  3  ω    -54.00 -28.00   0.50    2.00    --    5.00  45.00 150.00   52
  4  ω    -10.00  60.00   0.50    2.00    --    5.00  45.00 120.00  140
  5  ω     19.00  56.00   0.50    2.00    --    5.00  45.00  90.00   74
  6  ω      5.00  31.00   0.50    2.00    --    5.00  45.00  30.00   52
  7  ω     62.00  94.00   0.50    2.00    --    5.00  45.00  30.00   64
  8  ω   -101.00  77.00   0.50    2.00    --  -11.60  45.00 150.00  356
  9  ω     37.00  63.00   0.50    2.00    --  -11.60  45.00 -18.31   52
 10  ω   -101.00 -35.00   0.50    2.00    --  -11.60  45.00 -18.31  132
 11  ω     25.00  53.00   0.50    2.00    --  -11.60  45.00  87.70   56
 12  ω    -98.00  19.00   0.50    2.00    --  -11.60  45.00  87.70  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0396808000
_diffrn_orient_matrix_UB_12      -0.0268604000
_diffrn_orient_matrix_UB_13      0.0315929000
_diffrn_orient_matrix_UB_21      0.0406146000
_diffrn_orient_matrix_UB_22      -0.0559728000
_diffrn_orient_matrix_UB_23      0.0000576000
_diffrn_orient_matrix_UB_31      0.0419076000
_diffrn_orient_matrix_UB_32      0.0285520000
_diffrn_orient_matrix_UB_33      0.0298348000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                4576
_reflns_number_total             4784
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.017
_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)+(0.0524P)²+0.1988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0831
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C18(H18), C14(H14), C12(H12), C19(H19), C21(H21), C13(H13),
 C20(H20)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
O1 O 0.86196(10) 0.85897(11) 0.53389(6) 0.0328(2) Uani 1 1 d . . . . .
O2 O 0.81073(11) 0.86008(10) 0.66826(6) 0.0341(2) Uani 1 1 d . . . . .
N2 N 0.55049(10) 0.60945(11) 0.59527(7) 0.0231(2) Uani 1 1 d . . . . .
H2 H 0.505753 0.607355 0.548959 0.028 Uiso 1 1 calc R U . . .
N1 N 0.95168(11) 0.71128(11) 0.62191(7) 0.0256(2) Uani 1 1 d . . . . .
C16 C 0.50337(12) 0.65610(12) 0.66782(8) 0.0223(2) Uani 1 1 d . . . . .
C5 C 0.75741(12) 0.52227(11) 0.53564(7) 0.0207(2) Uani 1 1 d . . . . .
C4 C 0.67987(12) 0.56587(12) 0.60586(7) 0.0207(2) Uani 1 1 d . . . . .
C3 C 0.71611(12) 0.58260(12) 0.68707(7) 0.0218(2) Uani 1 1 d . . . . .
C6 C 0.87857(12) 0.44266(12) 0.55125(7) 0.0222(2) Uani 1 1 d . . . . .
C11 C 0.60433(12) 0.64091(12) 0.72708(7) 0.0226(2) Uani 1 1 d . . . . .
C2 C 0.84975(12) 0.55793(13) 0.72494(8) 0.0244(2) Uani 1 1 d . . . . .
H2A H 0.882290 0.473029 0.705896 0.029 Uiso 1 1 calc R U . . .
H2B H 0.838729 0.552855 0.785098 0.029 Uiso 1 1 calc R U . . .
C17 C 0.72378(14) 0.54963(13) 0.45825(8) 0.0266(2) Uani 1 1 d . . . . .
H17A H 0.646481 0.599433 0.447274 0.032 Uiso 1 1 calc R U . . .
H17B H 0.777205 0.519239 0.414312 0.032 Uiso 1 1 calc R U . . .
C9 C 0.87357(13) 0.81273(13) 0.60252(8) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.95715(14) 0.66069(14) 0.70546(8) 0.0277(3) Uani 1 1 d . . . . .
H1A H 0.946948 0.733277 0.744280 0.033 Uiso 1 1 calc R U . . .
H1B H 1.046095 0.622291 0.714674 0.033 Uiso 1 1 calc R U . . .
C7 C 1.00439(13) 0.49852(12) 0.56042(8) 0.0245(3) Uani 1 1 d . . . . .
C15 C 0.38132(13) 0.71458(13) 0.68534(9) 0.0274(3) Uani 1 1 d . . . . .
H15 H 0.313945 0.722374 0.644826 0.033 Uiso 1 1 calc R U . . .
C18 C 0.86470(14) 0.30891(12) 0.55616(8) 0.0271(3) Uani 1 1 d . . . . .
H18 H 0.778983 0.271186 0.550882 0.033 Uiso 1 1 calc R U . . .
C14 C 0.36248(14) 0.76061(14) 0.76386(9) 0.0314(3) Uani 1 1 d . . . . .
H14 H 0.281227 0.802253 0.777444 0.038 Uiso 1 1 calc R U . . .
C12 C 0.58094(14) 0.68714(14) 0.80650(8) 0.0293(3) Uani 1 1 d . . . . .
H12 H 0.646635 0.677479 0.847893 0.035 Uiso 1 1 calc R U . . .
C19 C 0.97467(16) 0.23071(14) 0.56865(9) 0.0349(3) Uani 1 1 d . . . . .
H19 H 0.964579 0.139797 0.571227 0.042 Uiso 1 1 calc R U . . .
C21 C 1.11400(14) 0.41851(16) 0.57369(9) 0.0329(3) Uani 1 1 d . . . . .
H21 H 1.199911 0.455293 0.580305 0.039 Uiso 1 1 calc R U . . .
C8 C 1.02300(13) 0.64269(13) 0.55660(8) 0.0275(3) Uani 1 1 d . . . . .
H8A H 1.119133 0.662644 0.560693 0.033 Uiso 1 1 calc R U . . .
H8B H 0.991202 0.674327 0.502853 0.033 Uiso 1 1 calc R U . . .
C13 C 0.46141(15) 0.74685(15) 0.82389(9) 0.0335(3) Uani 1 1 d . . . . .
H13 H 0.445870 0.779197 0.877463 0.040 Uiso 1 1 calc R U . . .
C20 C 1.09861(16) 0.28560(16) 0.57731(10) 0.0376(4) Uani 1 1 d . . . . .
H20 H 1.174163 0.232217 0.585822 0.045 Uiso 1 1 calc R U . . .
C10 C 0.70993(19) 0.95594(16) 0.65241(11) 0.0428(4) Uani 1 1 d . . . . .
H10A H 0.642978 0.920355 0.615084 0.064 Uiso 1 1 calc R U . . .
H10B H 0.751112 1.031910 0.627348 0.064 Uiso 1 1 calc R U . . .
H10C H 0.667241 0.980665 0.704032 0.064 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 C9 1.2248(17) . ?
O2 C9 1.3388(16) . ?
O2 C10 1.443(2) . ?
N2 H2 0.8800 . ?
N2 C16 1.3646(16) . ?
N2 C4 1.3872(15) . ?
N1 C9 1.3509(18) . ?
N1 C1 1.4630(17) . ?
N1 C8 1.4689(17) . ?
C16 C11 1.4107(17) . ?
C16 C15 1.3979(17) . ?
C5 C4 1.4583(16) . ?
C5 C6 1.4931(17) . ?
C5 C17 1.3386(17) . ?
C4 C3 1.3862(17) . ?
C3 C11 1.4334(17) . ?
C3 C2 1.5002(17) . ?
C6 C7 1.3988(18) . ?
C6 C18 1.3975(18) . ?
C11 C12 1.4027(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5502(19) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 C21 1.3962(18) . ?
C7 C8 1.5094(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.381(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3861(19) . ?
C14 H14 0.9500 . ?
C14 C13 1.403(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.389(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C13 H13 0.9500 . ?
C20 H20 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C9 O2 C10 116.11(12) . . ?
C16 N2 H2 125.3 . . ?
C16 N2 C4 109.42(10) . . ?
C4 N2 H2 125.3 . . ?
C9 N1 C1 121.34(11) . . ?
C9 N1 C8 119.41(11) . . ?
C1 N1 C8 119.00(11) . . ?
N2 C16 C11 107.85(11) . . ?
N2 C16 C15 129.50(12) . . ?
C15 C16 C11 122.60(12) . . ?
C4 C5 C6 118.23(10) . . ?
C17 C5 C4 122.79(11) . . ?
C17 C5 C6 118.98(11) . . ?
N2 C4 C5 120.25(10) . . ?
C3 C4 N2 108.94(11) . . ?
C3 C4 C5 130.61(11) . . ?
C4 C3 C11 106.45(11) . . ?
C4 C3 C2 127.45(11) . . ?
C11 C3 C2 125.83(11) . . ?
C7 C6 C5 121.71(11) . . ?
C18 C6 C5 118.57(12) . . ?
C18 C6 C7 119.71(12) . . ?
C16 C11 C3 107.33(11) . . ?
C12 C11 C16 118.40(12) . . ?
C12 C11 C3 134.20(12) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C3 C2 C1 114.89(11) . . ?
H2A C2 H2B 107.5 . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C5 C17 H17A 120.0 . . ?
C5 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
O1 C9 O2 123.03(13) . . ?
O1 C9 N1 125.11(12) . . ?
O2 C9 N1 111.85(12) . . ?
N1 C1 C2 114.35(11) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C6 C7 C8 121.23(11) . . ?
C21 C7 C6 118.87(12) . . ?
C21 C7 C8 119.89(12) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 C16 117.41(12) . . ?
C14 C15 H15 121.3 . . ?
C6 C18 H18 119.6 . . ?
C19 C18 C6 120.71(14) . . ?
C19 C18 H18 119.6 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 121.08(13) . . ?
C13 C14 H14 119.5 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.29(13) . . ?
C13 C12 H12 120.4 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.59(13) . . ?
C20 C19 H19 120.2 . . ?
C7 C21 H21 119.7 . . ?
C20 C21 C7 120.63(14) . . ?
C20 C21 H21 119.7 . . ?
N1 C8 C7 112.96(11) . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.20(13) . . ?
C12 C13 H13 119.4 . . ?
C19 C20 C21 120.48(13) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
N2 C16 C11 C3 0.08(14) . . . . ?
N2 C16 C11 C12 177.40(12) . . . . ?
N2 C16 C15 C14 -175.97(13) . . . . ?
N2 C4 C3 C11 -0.98(14) . . . . ?
N2 C4 C3 C2 -175.26(12) . . . . ?
C16 N2 C4 C5 -174.26(11) . . . . ?
C16 N2 C4 C3 1.06(14) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
C16 C15 C14 C13 -1.1(2) . . . . ?
C5 C4 C3 C11 173.70(12) . . . . ?
C5 C4 C3 C2 -0.6(2) . . . . ?
C5 C6 C7 C21 -179.05(12) . . . . ?
C5 C6 C7 C8 1.25(18) . . . . ?
C5 C6 C18 C19 178.48(12) . . . . ?
C4 N2 C16 C11 -0.69(14) . . . . ?
C4 N2 C16 C15 176.85(12) . . . . ?
C4 C5 C6 C7 -91.64(14) . . . . ?
C4 C5 C6 C18 88.79(14) . . . . ?
C4 C3 C11 C16 0.55(14) . . . . ?
C4 C3 C11 C12 -176.16(15) . . . . ?
C4 C3 C2 C1 75.26(17) . . . . ?
C3 C11 C12 C13 175.75(14) . . . . ?
C3 C2 C1 N1 -37.83(16) . . . . ?
C6 C5 C4 N2 -162.89(11) . . . . ?
C6 C5 C4 C3 22.9(2) . . . . ?
C6 C7 C21 C20 0.3(2) . . . . ?
C6 C7 C8 N1 62.42(16) . . . . ?
C6 C18 C19 C20 0.8(2) . . . . ?
C11 C16 C15 C14 1.24(19) . . . . ?
C11 C3 C2 C1 -97.97(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C2 C3 C11 C16 174.95(12) . . . . ?
C2 C3 C11 C12 -1.8(2) . . . . ?
C17 C5 C4 N2 16.48(19) . . . . ?
C17 C5 C4 C3 -157.69(14) . . . . ?
C17 C5 C6 C7 88.97(15) . . . . ?
C17 C5 C6 C18 -90.60(15) . . . . ?
C9 N1 C1 C2 87.47(15) . . . . ?
C9 N1 C8 C7 -130.31(13) . . . . ?
C1 N1 C9 O1 -178.65(13) . . . . ?
C1 N1 C9 O2 2.62(17) . . . . ?
C1 N1 C8 C7 44.04(16) . . . . ?
C7 C6 C18 C19 -1.1(2) . . . . ?
C7 C21 C20 C19 -0.6(2) . . . . ?
C15 C16 C11 C3 -177.67(11) . . . . ?
C15 C16 C11 C12 -0.34(19) . . . . ?
C15 C14 C13 C12 0.1(2) . . . . ?
C18 C6 C7 C21 0.51(18) . . . . ?
C18 C6 C7 C8 -179.19(12) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C21 C7 C8 N1 -117.28(14) . . . . ?
C8 N1 C9 O1 -4.4(2) . . . . ?
C8 N1 C9 O2 176.85(11) . . . . ?
C8 N1 C1 C2 -86.78(15) . . . . ?
C8 C7 C21 C20 -179.95(13) . . . . ?
C10 O2 C9 O1 10.2(2) . . . . ?
C10 O2 C9 N1 -171.08(13) . . . . ?

_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.571
####################################################################### 
# 
# 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_mx8755
_database_code_depnum_ccdc_archive 'CCDC 2047497'
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2020-09-29
_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        ?
_chemical_formula_moiety         'C19 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONBr
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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   10.72690(10)
_cell_length_b                   10.72690(10)
_cell_length_c                   14.5422(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1673.32(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24486
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.0460
_cell_measurement_theta_min      1.8560
_shelx_estimated_absorpt_T_max   0.478
_shelx_estimated_absorpt_T_min   0.365
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.761
_diffrn_reflns_theta_min         1.898
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    0.80    --    5.00  45.00 120.00  356
  2  ω   -104.00  74.00   0.50    0.80    --  -14.80  45.00 120.00  356
  3  ω   -104.00  74.00   0.50    0.80    --  -14.80  45.00  -6.10  356
  4  ω   -104.00  74.00   0.50    0.80    --  -14.80  45.00 173.74  356
  5  ω   -104.00  74.00   0.50    0.80    --  -14.80  45.00  60.00  356
  6  ω    -84.00 -23.00   0.50    0.80    --    5.00  45.00  90.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0207199000
_diffrn_orient_matrix_UB_12      -0.0352564000
_diffrn_orient_matrix_UB_13      0.0383438000
_diffrn_orient_matrix_UB_21      0.0422691000
_diffrn_orient_matrix_UB_22      -0.0326731000
_diffrn_orient_matrix_UB_23      -0.0287578000
_diffrn_orient_matrix_UB_31      0.0464994000
_diffrn_orient_matrix_UB_32      0.0453147000
_diffrn_orient_matrix_UB_33      0.0091155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                4343
_reflns_number_total             4706
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4706
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.060
_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)+(0.0293P)²+0.3079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0574
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C6(H6), C17(H17), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.85924(2) -0.08891(3) 0.16716(2) 0.03513(8) Uani 1 1 d . . . . .
O3 O 0.64306(18) 0.25356(18) 0.79979(12) 0.0306(4) Uani 1 1 d . . . . .
O1 O 0.44078(17) 0.23020(18) 0.27045(13) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.73703(17) 0.04303(18) 0.74787(13) 0.0313(4) Uani 1 1 d . . . . .
N1 N 0.41189(18) 0.12702(18) 0.40803(18) 0.0259(4) Uani 1 1 d . . . . .
C4 C 0.5755(2) -0.0107(2) 0.40204(15) 0.0205(4) Uani 1 1 d . . . . .
C14 C 0.6059(2) 0.0364(2) 0.61133(16) 0.0215(4) Uani 1 1 d . . . . .
H14 H 0.637391 -0.042963 0.593951 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5718(2) 0.0584(2) 0.32125(15) 0.0206(4) Uani 1 1 d . . . . .
C6 C 0.6532(2) 0.0376(2) 0.24885(15) 0.0211(4) Uani 1 1 d . . . . .
H6 H 0.649938 0.086000 0.194214 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4692(2) 0.1500(2) 0.32679(16) 0.0238(5) Uani 1 1 d . . . . .
C1 C 0.7391(2) -0.0568(2) 0.25989(16) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.4699(2) 0.2110(2) 0.58137(17) 0.0250(5) Uani 1 1 d . . . . .
C10 C 0.5186(2) 0.0967(2) 0.55452(15) 0.0215(4) Uani 1 1 d . . . . .
C17 C 0.5089(2) 0.2635(2) 0.66507(19) 0.0258(4) Uani 1 1 d . . . . .
H17 H 0.474262 0.340716 0.684362 0.031 Uiso 1 1 calc R . . . .
C16 C 0.5964(2) 0.2056(2) 0.71983(15) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.7419(2) -0.1309(2) 0.33871(18) 0.0276(5) Uani 1 1 d . . . . .
H2 H 0.800642 -0.196827 0.343303 0.033 Uiso 1 1 calc R . . . .
C7 C 0.4731(2) 0.0329(2) 0.46626(16) 0.0223(4) Uani 1 1 d . . . . .
C3 C 0.6596(2) -0.1090(2) 0.41026(18) 0.0274(5) Uani 1 1 d . . . . .
H3 H 0.660580 -0.159888 0.463742 0.033 Uiso 1 1 calc R . . . .
C15 C 0.6465(2) 0.0908(2) 0.69202(16) 0.0235(5) Uani 1 1 d . . . . .
C9 C 0.3836(3) -0.0739(3) 0.48842(18) 0.0308(6) Uani 1 1 d . . . . .
H9A H 0.314665 -0.042393 0.526059 0.046 Uiso 1 1 calc GR . . . .
H9B H 0.428240 -0.138998 0.522326 0.046 Uiso 1 1 calc GR . . . .
H9C H 0.350529 -0.108682 0.431087 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.3190(2) 0.2088(3) 0.44821(18) 0.0316(6) Uani 1 1 d . . . . .
H13A H 0.249724 0.158798 0.473856 0.038 Uiso 1 1 calc R . . . .
H13B H 0.284654 0.264767 0.400365 0.038 Uiso 1 1 calc R . . . .
C18 C 0.8052(3) -0.0623(3) 0.7147(2) 0.0345(6) Uani 1 1 d . . . . .
H18A H 0.843367 -0.041851 0.655387 0.052 Uiso 1 1 calc GR . . . .
H18B H 0.748473 -0.133169 0.707093 0.052 Uiso 1 1 calc GR . . . .
H18C H 0.870555 -0.084154 0.758995 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.3790(3) 0.2854(3) 0.5238(2) 0.0354(6) Uani 1 1 d . . . . .
H12A H 0.423365 0.356915 0.495837 0.042 Uiso 1 1 calc R . . . .
H12B H 0.312869 0.319205 0.564282 0.042 Uiso 1 1 calc R . . . .
C19 C 0.5896(3) 0.3672(3) 0.8325(2) 0.0412(7) Uani 1 1 d . . . . .
H19A H 0.604306 0.433577 0.787498 0.062 Uiso 1 1 calc GR . . . .
H19B H 0.628051 0.389891 0.891253 0.062 Uiso 1 1 calc GR . . . .
H19C H 0.499660 0.355958 0.841106 0.062 Uiso 1 1 calc GR . . . .


_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 C1 1.897(2) . ?
O3 C16 1.367(3) . ?
O3 C19 1.428(3) . ?
O1 C8 1.227(3) . ?
O2 C15 1.366(3) . ?
O2 C18 1.430(3) . ?
N1 C8 1.354(3) . ?
N1 C7 1.472(3) . ?
N1 C13 1.450(3) . ?
C4 C5 1.390(3) . ?
C4 C7 1.516(3) . ?
C4 C3 1.394(3) . ?
C14 C10 1.406(3) . ?
C14 C15 1.381(3) . ?
C5 C6 1.386(3) . ?
C5 C8 1.478(3) . ?
C6 C1 1.378(3) . ?
C1 C2 1.395(3) . ?
C11 C10 1.389(3) . ?
C11 C17 1.405(4) . ?
C11 C12 1.513(4) . ?
C10 C7 1.534(3) . ?
C17 C16 1.378(3) . ?
C16 C15 1.403(3) . ?
C2 C3 1.384(4) . ?
C7 C9 1.529(3) . ?
C13 C12 1.516(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 C19 117.2(2) . . ?
C15 O2 C18 117.4(2) . . ?
C8 N1 C7 115.08(19) . . ?
C8 N1 C13 123.6(2) . . ?
C13 N1 C7 119.3(2) . . ?
C5 C4 C7 109.63(19) . . ?
C5 C4 C3 119.6(2) . . ?
C3 C4 C7 130.6(2) . . ?
C15 C14 C10 121.0(2) . . ?
C4 C5 C8 109.2(2) . . ?
C6 C5 C4 122.6(2) . . ?
C6 C5 C8 128.2(2) . . ?
C1 C6 C5 116.8(2) . . ?
O1 C8 N1 126.7(2) . . ?
O1 C8 C5 128.0(2) . . ?
N1 C8 C5 105.36(19) . . ?
C6 C1 Br1 120.30(18) . . ?
C6 C1 C2 121.9(2) . . ?
C2 C1 Br1 117.79(18) . . ?
C10 C11 C17 119.0(2) . . ?
C10 C11 C12 123.6(2) . . ?
C17 C11 C12 117.4(2) . . ?
C14 C10 C7 119.9(2) . . ?
C11 C10 C14 119.4(2) . . ?
C11 C10 C7 120.6(2) . . ?
C16 C17 C11 121.5(2) . . ?
O3 C16 C17 124.9(2) . . ?
O3 C16 C15 115.8(2) . . ?
C17 C16 C15 119.3(2) . . ?
C3 C2 C1 120.5(2) . . ?
N1 C7 C4 100.40(18) . . ?
N1 C7 C10 108.50(19) . . ?
N1 C7 C9 110.8(2) . . ?
C4 C7 C10 115.01(19) . . ?
C4 C7 C9 110.7(2) . . ?
C9 C7 C10 110.93(19) . . ?
C2 C3 C4 118.5(2) . . ?
O2 C15 C14 124.8(2) . . ?
O2 C15 C16 115.5(2) . . ?
C14 C15 C16 119.7(2) . . ?
N1 C13 C12 109.2(2) . . ?
C11 C12 C13 112.9(2) . . ?

_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 1.969
_oxdiff_exptl_absorpt_empirical_full_min 0.565
