# Electronic Supplementary Material (ESI) for ChemComm.
# 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_lauvin2
_database_code_depnum_ccdc_archive 'CCDC 2104570'
loop_
_audit_author_name
_audit_author_address
'Daniel Chartrand'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2020-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.1178(3)
_cell_length_b                   18.3487(7)
_cell_length_c                   8.0923(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1353.84(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7396
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.927
_cell_measurement_theta_min      5.418
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1331 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.7222.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Slow evaporation in ether'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17932
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.049
_diffrn_reflns_theta_min         5.417
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2565
_reflns_number_total             2599
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.047
_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)+(0.0656P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_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 0.49458(14) 0.17453(7) 0.66680(17) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.39268(16) 0.27677(9) 0.56058(18) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.4331(2) 0.09377(10) 0.3804(2) 0.0298(4) Uani 1 1 d . . . . .
H1A H 0.341950 0.085810 0.444256 0.036 Uiso 1 1 calc R U . . .
H1B H 0.513475 0.067384 0.436886 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4139(2) 0.06302(11) 0.2069(3) 0.0329(4) Uani 1 1 d . . . . .
H2A H 0.320205 0.080551 0.159530 0.039 Uiso 1 1 calc R U . . .
H2B H 0.410250 0.009143 0.211928 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5410(2) 0.08687(11) 0.0967(3) 0.0337(4) Uani 1 1 d . . . . .
H3A H 0.634504 0.068989 0.143842 0.040 Uiso 1 1 calc R U . . .
H3B H 0.529252 0.065177 -0.014527 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5461(2) 0.16944(11) 0.0822(3) 0.0341(4) Uani 1 1 d . . . . .
H4A H 0.643161 0.183941 0.038463 0.041 Uiso 1 1 calc R U . . .
H4B H 0.470942 0.185287 0.001512 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5200(2) 0.20850(10) 0.2436(2) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.4681(2) 0.17442(10) 0.3773(3) 0.0268(4) Uani 1 1 d . . . . .
C7 C 0.5557(2) 0.28905(10) 0.2477(3) 0.0318(4) Uani 1 1 d . . . . .
H7A H 0.632440 0.298470 0.331476 0.038 Uiso 1 1 calc R U . . .
H7B H 0.593745 0.304585 0.138646 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4203(2) 0.33186(10) 0.2891(2) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.383766 0.365785 0.210580 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3499(2) 0.32405(9) 0.4312(2) 0.0300(4) Uani 1 1 d . . . . .
H9 H 0.263994 0.352437 0.447554 0.036 Uiso 1 1 calc R U . . .
C10 C 0.45592(18) 0.20906(10) 0.5439(2) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.3606(2) 0.30419(10) 0.7278(2) 0.0292(4) Uani 1 1 d . . . . .
H11A H 0.369269 0.263508 0.807619 0.035 Uiso 1 1 calc R U . . .
H11B H 0.258110 0.321957 0.731277 0.035 Uiso 1 1 calc R U . . .
C12 C 0.46220(19) 0.36527(10) 0.7804(2) 0.0257(4) Uani 1 1 d . . . . .
C13 C 0.61301(19) 0.36138(10) 0.7523(2) 0.0293(4) Uani 1 1 d . . . . .
H13 H 0.652832 0.320610 0.695508 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7050(2) 0.41643(10) 0.8063(2) 0.0318(4) Uani 1 1 d . . . . .
H14 H 0.807522 0.413363 0.786316 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6478(2) 0.47614(11) 0.8898(2) 0.0336(4) Uani 1 1 d . . . . .
H15 H 0.711176 0.513660 0.927697 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4981(2) 0.48100(10) 0.9177(3) 0.0352(5) Uani 1 1 d . . . . .
H16 H 0.458697 0.521931 0.974255 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4057(2) 0.42564(10) 0.8626(3) 0.0314(4) Uani 1 1 d . . . . .
H17 H 0.303091 0.429159 0.881375 0.038 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 C10 1.231(2) . ?
N1 C9 1.414(2) . ?
N1 C10 1.376(2) . ?
N1 C11 1.473(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.523(3) . ?
C1 C6 1.514(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.520(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.509(3) . ?
C5 C6 1.336(3) . ?
C5 C7 1.514(2) . ?
C6 C10 1.495(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.501(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.325(3) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(2) . ?
C12 C13 1.396(2) . ?
C12 C17 1.391(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C11 114.56(15) . . ?
C10 N1 C9 126.62(16) . . ?
C10 N1 C11 118.80(15) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C6 C1 H1A 109.3 . . ?
C6 C1 H1B 109.3 . . ?
C6 C1 C2 111.79(16) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 C3 110.17(16) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.72(16) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.70(17) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 C7 116.68(17) . . ?
C6 C5 C4 122.29(17) . . ?
C6 C5 C7 121.03(18) . . ?
C5 C6 C1 123.06(18) . . ?
C5 C6 C10 123.88(16) . . ?
C10 C6 C1 112.65(16) . . ?
C5 C7 H7A 109.7 . . ?
C5 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C5 109.83(16) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.40(17) . . ?
C9 C8 H8 118.8 . . ?
N1 C9 H9 117.4 . . ?
C8 C9 N1 125.11(17) . . ?
C8 C9 H9 117.4 . . ?
O1 C10 N1 120.34(18) . . ?
O1 C10 C6 119.25(16) . . ?
N1 C10 C6 120.25(15) . . ?
N1 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
N1 C11 C12 112.90(15) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C13 C12 C11 121.25(16) . . ?
C17 C12 C11 119.80(16) . . ?
C17 C12 C13 118.92(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.56(17) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.09(17) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.02(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.76(17) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.65(18) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?

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
N1 C11 C12 C13 -44.1(2) . . . . ?
N1 C11 C12 C17 137.71(18) . . . . ?
C1 C2 C3 C4 -61.2(2) . . . . ?
C1 C6 C10 O1 36.8(2) . . . . ?
C1 C6 C10 N1 -138.64(16) . . . . ?
C2 C1 C6 C5 -19.3(3) . . . . ?
C2 C1 C6 C10 167.73(16) . . . . ?
C2 C3 C4 C5 42.5(2) . . . . ?
C3 C4 C5 C6 -12.9(3) . . . . ?
C3 C4 C5 C7 167.08(16) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C10 173.19(18) . . . . ?
C4 C5 C7 C8 119.92(19) . . . . ?
C5 C6 C10 O1 -136.04(18) . . . . ?
C5 C6 C10 N1 48.5(3) . . . . ?
C5 C7 C8 C9 62.0(2) . . . . ?
C6 C1 C2 C3 48.5(2) . . . . ?
C6 C5 C7 C8 -60.1(2) . . . . ?
C7 C5 C6 C1 -178.98(17) . . . . ?
C7 C5 C6 C10 -6.8(3) . . . . ?
C7 C8 C9 N1 1.1(3) . . . . ?
C9 N1 C10 O1 176.56(16) . . . . ?
C9 N1 C10 C6 -8.0(3) . . . . ?
C9 N1 C11 C12 -73.42(19) . . . . ?
C10 N1 C9 C8 -35.6(3) . . . . ?
C10 N1 C11 C12 108.16(17) . . . . ?
C11 N1 C9 C8 146.13(19) . . . . ?
C11 N1 C10 O1 -5.2(2) . . . . ?
C11 N1 C10 C6 170.20(16) . . . . ?
C11 C12 C13 C14 -177.67(18) . . . . ?
C11 C12 C17 C16 177.46(17) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C12 C17 C16 -0.7(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(3)
2 0.1(3)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cha233
_database_code_depnum_ccdc_archive 'CCDC 2104571'
loop_
_audit_author_name
_audit_author_address
'Chartrand D.'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2020-08-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 Br N O'
_chemical_formula_sum            'C11 H16 Br N O'
_chemical_formula_weight         258.16
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   10.6041(4)
_cell_length_b                   9.5540(3)
_cell_length_c                   11.2772(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.1440(10)
_cell_angle_gamma                90
_cell_volume                     1127.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    120
_cell_measurement_theta_max      73.400
_cell_measurement_theta_min      3.674
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    3.114
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.5605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.7437.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27326
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         73.468
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.85
_diffrn_source_power             0.199215
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3138
_reflns_number_total             3440
_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       
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.096
_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)+(0.0340P)²+0.5812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0751
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.46920(2) 0.69276(2) 0.50922(2) 0.02916(7) Uani 1 1 d . . . . .
O1 O 0.10496(11) 0.66609(11) 0.38810(9) 0.0266(2) Uani 1 1 d . . . . .
N1 N 0.18965(11) 0.51960(11) 0.53843(11) 0.0225(2) Uani 1 1 d . . . . .
C1 C 0.22497(13) 0.77367(13) 0.55756(11) 0.0207(2) Uani 1 1 d . . . . .
C2 C 0.34819(14) 0.80748(13) 0.57385(13) 0.0225(2) Uani 1 1 d . . . . .
C3 C 0.40683(15) 0.93476(16) 0.63753(15) 0.0296(3) Uani 1 1 d . . . . .
H3A H 0.436539 0.997091 0.579921 0.035 Uiso 1 1 calc R U . . .
H3B H 0.480066 0.907301 0.695746 0.035 Uiso 1 1 calc R U . . .
C4 C 0.31096(16) 1.01194(16) 0.70160(15) 0.0313(3) Uani 1 1 d . . . . .
H4A H 0.301670 0.962867 0.775014 0.038 Uiso 1 1 calc R U . . .
H4B H 0.342088 1.105538 0.722848 0.038 Uiso 1 1 calc R U . . .
C5 C 0.18181(16) 1.02068(15) 0.62039(14) 0.0296(3) Uani 1 1 d . . . . .
H5A H 0.191623 1.066702 0.545726 0.036 Uiso 1 1 calc R U . . .
H5B H 0.123277 1.075722 0.659304 0.036 Uiso 1 1 calc R U . . .
C6 C 0.12737(14) 0.87408(14) 0.59402(13) 0.0248(3) Uani 1 1 d . . . . .
H6A H 0.097343 0.838139 0.664989 0.030 Uiso 1 1 calc R U . . .
H6B H 0.054693 0.879446 0.529999 0.030 Uiso 1 1 calc R U . . .
C7 C 0.16993(13) 0.64786(13) 0.48778(12) 0.0209(2) Uani 1 1 d . . . . .
C8 C 0.15032(15) 0.39590(14) 0.46534(14) 0.0275(3) Uani 1 1 d . . . . .
H8A H 0.095537 0.423830 0.393120 0.041 Uiso 1 1 calc R U . . .
H8B H 0.105120 0.332847 0.509896 0.041 Uiso 1 1 calc R U . . .
H8C H 0.224489 0.349870 0.445053 0.041 Uiso 1 1 calc R U . . .
C9 C 0.26648(14) 0.49366(13) 0.65371(13) 0.0245(2) Uani 1 1 d . . . . .
H9 H 0.357763 0.479446 0.652358 0.029 Uiso 1 1 calc R U . . .
C10 C 0.23467(19) 0.56001(16) 0.76508(14) 0.0335(3) Uani 1 1 d . . . . .
H10A H 0.161104 0.621626 0.757078 0.040 Uiso 1 1 calc R U . . .
H10B H 0.304961 0.586969 0.826750 0.040 Uiso 1 1 calc R U . . .
C11 C 0.21076(17) 0.40611(16) 0.74358(14) 0.0305(3) Uani 1 1 d . . . . .
H11A H 0.122905 0.375298 0.722363 0.037 Uiso 1 1 calc R U . . .
H11B H 0.266844 0.340620 0.792075 0.037 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
Br1 C2 1.9174(14) . ?
O1 C7 1.2339(17) . ?
N1 C7 1.3542(17) . ?
N1 C8 1.4631(17) . ?
N1 C9 1.4417(18) . ?
C1 C2 1.330(2) . ?
C1 C6 1.5151(19) . ?
C1 C7 1.5029(18) . ?
C2 C3 1.4965(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.527(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.524(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5261(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C10 1.492(2) . ?
C9 C11 1.505(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.505(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C7 N1 C8 118.83(12) . . ?
C7 N1 C9 124.28(11) . . ?
C9 N1 C8 116.03(11) . . ?
C2 C1 C6 120.48(12) . . ?
C2 C1 C7 123.90(12) . . ?
C7 C1 C6 115.04(11) . . ?
C1 C2 Br1 120.72(10) . . ?
C1 C2 C3 126.00(13) . . ?
C3 C2 Br1 113.25(11) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.24(13) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.14(12) . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 110.04(12) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C1 C6 C5 112.36(12) . . ?
C1 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 N1 122.58(12) . . ?
O1 C7 C1 118.58(12) . . ?
N1 C7 C1 118.80(11) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9 115.3 . . ?
N1 C9 C10 120.99(12) . . ?
N1 C9 C11 118.46(12) . . ?
C10 C9 H9 115.3 . . ?
C10 C9 C11 60.27(10) . . ?
C11 C9 H9 115.3 . . ?
C9 C10 H10A 117.7 . . ?
C9 C10 H10B 117.7 . . ?
C9 C10 C11 60.29(10) . . ?
H10A C10 H10B 114.9 . . ?
C11 C10 H10A 117.7 . . ?
C11 C10 H10B 117.7 . . ?
C9 C11 H11A 117.8 . . ?
C9 C11 H11B 117.8 . . ?
C10 C11 C9 59.44(10) . . ?
C10 C11 H11A 117.8 . . ?
C10 C11 H11B 117.8 . . ?
H11A C11 H11B 115.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 -172.36(10) . . . . ?
N1 C9 C10 C11 107.29(15) . . . . ?
N1 C9 C11 C10 -111.40(15) . . . . ?
C1 C2 C3 C4 9.6(2) . . . . ?
C2 C1 C6 C5 13.31(18) . . . . ?
C2 C1 C7 O1 -107.47(16) . . . . ?
C2 C1 C7 N1 74.88(18) . . . . ?
C2 C3 C4 C5 -43.59(17) . . . . ?
C3 C4 C5 C6 63.49(17) . . . . ?
C4 C5 C6 C1 -47.28(17) . . . . ?
C6 C1 C2 Br1 -171.76(10) . . . . ?
C6 C1 C2 C3 6.2(2) . . . . ?
C6 C1 C7 O1 63.80(17) . . . . ?
C6 C1 C7 N1 -113.84(14) . . . . ?
C7 N1 C9 C10 59.48(19) . . . . ?
C7 N1 C9 C11 130.07(14) . . . . ?
C7 C1 C2 Br1 -0.93(19) . . . . ?
C7 C1 C2 C3 176.99(13) . . . . ?
C7 C1 C6 C5 -158.29(12) . . . . ?
C8 N1 C7 O1 10.1(2) . . . . ?
C8 N1 C7 C1 -172.36(12) . . . . ?
C8 N1 C9 C10 -131.35(14) . . . . ?
C8 N1 C9 C11 -60.77(17) . . . . ?
C9 N1 C7 O1 178.98(13) . . . . ?
C9 N1 C7 C1 -3.5(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop.'
_olex2_submission_special_instructions 'No special instructions were received'
