# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_190329_jf_3_020_0m
_database_code_depnum_ccdc_archive 'CCDC 1956055'
loop_
_audit_author_name
_audit_author_address
liujiyong
;Zhejiang University
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 Br N'
_chemical_formula_sum            'C19 H16 Br N'
_chemical_formula_weight         338.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.077(4)
_cell_length_b                   5.678(3)
_cell_length_c                   13.478(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.922(17)
_cell_angle_gamma                90
_cell_volume                     765.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.91
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.368
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1466 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.6670.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.064
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17069
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.014
_diffrn_reflns_theta_min         2.391
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4253
_reflns_number_total             4827
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.042
_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)+(0.0251P)²+0.0365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0749
_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:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84588(2) 0.54743(9) 0.45905(2) 0.06726(13) Uani 1 1 d . . . . .
N1 N 0.17033(18) 0.3605(3) 0.10930(12) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.27620(19) 0.5756(4) -0.11714(14) 0.0285(4) Uani 1 1 d . . . . .
H1 H 0.328896 0.702823 -0.136171 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2185(2) 0.4181(4) -0.18794(17) 0.0335(4) Uani 1 1 d . . . . .
H2 H 0.232959 0.437491 -0.255830 0.040 Uiso 1 1 calc R . . . .
C3 C 0.1390(3) 0.2297(4) -0.16159(17) 0.0355(5) Uani 1 1 d . . . . .
H3 H 0.100688 0.124494 -0.211913 0.043 Uiso 1 1 calc R . . . .
C4 C 0.1157(2) 0.1953(4) -0.06355(16) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.061475 0.069310 -0.045426 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1753(2) 0.3540(3) 0.00778(15) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.25573(17) 0.5448(4) -0.01691(13) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.3010(2) 0.6648(3) 0.07453(15) 0.0267(4) Uani 1 1 d . . . . .
C8 C 0.24626(18) 0.5490(4) 0.14948(13) 0.0262(3) Uani 1 1 d . . . . .
C9 C 0.2597(2) 0.5979(3) 0.25986(15) 0.0298(4) Uani 1 1 d . . . . .
H9 H 0.225473 0.760861 0.268978 0.036 Uiso 1 1 calc R . . . .
C10 C 0.1760(3) 0.4308(5) 0.31364(18) 0.0389(5) Uani 1 1 d . . . . .
H10 H 0.174356 0.454333 0.383268 0.047 Uiso 1 1 calc R . . . .
C11 C 0.1051(3) 0.2552(4) 0.27121(18) 0.0389(5) Uani 1 1 d . . . . .
H11 H 0.058669 0.157807 0.312781 0.047 Uiso 1 1 calc R . . . .
C12 C 0.0927(2) 0.1985(4) 0.16248(16) 0.0316(4) Uani 1 1 d . . . . .
H12A H 0.124199 0.035609 0.153493 0.038 Uiso 1 1 calc R . . . .
H12B H -0.002450 0.207201 0.134080 0.038 Uiso 1 1 calc R . . . .
C13 C 0.3956(2) 0.8683(4) 0.08502(18) 0.0352(5) Uani 1 1 d . . . . .
H13A H 0.487163 0.810981 0.083955 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.388785 0.949062 0.148456 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.372978 0.978266 0.029521 0.053 Uiso 1 1 calc GR . . . .
C14 C 0.4037(2) 0.5893(3) 0.30888(14) 0.0274(4) Uani 1 1 d . . . . .
C15 C 0.4869(3) 0.4048(4) 0.2888(2) 0.0429(6) Uani 1 1 d . . . . .
H15 H 0.453645 0.285202 0.243101 0.052 Uiso 1 1 calc R . . . .
C16 C 0.6172(3) 0.3921(5) 0.3341(2) 0.0462(6) Uani 1 1 d . . . . .
H16 H 0.673138 0.265070 0.319726 0.055 Uiso 1 1 calc R . . . .
C17 C 0.6652(2) 0.5657(5) 0.40058(14) 0.0370(4) Uani 1 1 d . . . . .
C18 C 0.5854(3) 0.7500(4) 0.42315(18) 0.0412(5) Uani 1 1 d . . . . .
H18 H 0.618960 0.867993 0.469524 0.049 Uiso 1 1 calc R . . . .
C19 C 0.4545(3) 0.7600(4) 0.37658(17) 0.0359(5) Uani 1 1 d . . . . .
H19 H 0.398661 0.886715 0.391559 0.043 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C17 1.898(2) . ?
N1 C5 1.376(3) . ?
N1 C8 1.387(3) . ?
N1 C12 1.452(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.408(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.434(3) . ?
C7 C8 1.375(3) . ?
C7 C13 1.494(3) . ?
C8 C9 1.503(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.511(3) . ?
C9 C14 1.521(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.316(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.491(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.389(3) . ?
C14 C19 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(4) . ?
C19 H19 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
C5 N1 C8 108.94(16) . . ?
C5 N1 C12 124.09(17) . . ?
C8 N1 C12 126.93(17) . . ?
C2 C1 H1 120.5 . . ?
C2 C1 C6 119.05(19) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 129.55(19) . . ?
N1 C5 C6 107.67(16) . . ?
C4 C5 C6 122.78(19) . . ?
C1 C6 C5 118.47(17) . . ?
C1 C6 C7 134.47(18) . . ?
C5 C6 C7 107.05(16) . . ?
C6 C7 C13 125.60(19) . . ?
C8 C7 C6 106.87(17) . . ?
C8 C7 C13 127.45(19) . . ?
N1 C8 C9 120.56(17) . . ?
C7 C8 N1 109.46(16) . . ?
C7 C8 C9 129.98(18) . . ?
C8 C9 H9 107.5 . . ?
C8 C9 C10 111.70(18) . . ?
C8 C9 C14 113.02(16) . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C14 109.27(17) . . ?
C14 C9 H9 107.5 . . ?
C9 C10 H10 117.6 . . ?
C11 C10 C9 124.9(2) . . ?
C11 C10 H10 117.6 . . ?
C10 C11 H11 117.7 . . ?
C10 C11 C12 124.6(2) . . ?
C12 C11 H11 117.7 . . ?
N1 C12 C11 111.23(18) . . ?
N1 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C9 120.41(18) . . ?
C19 C14 C9 121.38(18) . . ?
C19 C14 C15 118.2(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 Br1 118.34(19) . . ?
C18 C17 Br1 120.44(18) . . ?
C18 C17 C16 121.2(2) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C14 C19 C18 121.5(2) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_190513_jf_3_084_0m
_database_code_depnum_ccdc_archive 'CCDC 1956072'
loop_
_audit_author_name
_audit_author_address
liujiyong
;Zhejiang University
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 Cl N O'
_chemical_formula_sum            'C17 H20 Cl N O'
_chemical_formula_weight         289.79
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.4093(8)
_cell_length_b                   6.0139(4)
_cell_length_c                   12.2223(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.849(3)
_cell_angle_gamma                90
_cell_volume                     751.45(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8035
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.8684.
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    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.686
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.134
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8776
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.169
_diffrn_reflns_theta_min         2.361
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3100
_reflns_number_total             3198
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.168
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.053
_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)+(0.0311P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0644
_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:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C)
;
_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
Cl1 Cl 0.20608(4) 0.90023(7) 0.24281(4) 0.03262(12) Uani 1 1 d . . . . .
O1 O 0.11366(13) 0.5064(3) 0.65530(11) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.40949(14) 0.3654(3) 0.33422(12) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.17622(16) 0.6132(3) 0.47977(14) 0.0259(4) Uani 1 1 d . . . . .
H1 H 0.119308 0.738076 0.469170 0.031 Uiso 1 1 calc R . . . .
C2 C 0.18308(17) 0.4754(3) 0.57149(15) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.26505(18) 0.2871(3) 0.58628(15) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.265993 0.194679 0.649450 0.036 Uiso 1 1 calc R . . . .
C4 C 0.34414(19) 0.2337(3) 0.51104(15) 0.0294(4) Uani 1 1 d . . . . .
H4 H 0.399211 0.106483 0.521083 0.035 Uiso 1 1 calc R . . . .
C5 C 0.33958(16) 0.3747(3) 0.41976(14) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.25670(17) 0.5613(3) 0.40295(14) 0.0248(4) Uani 1 1 d . . . . .
C7 C 0.28034(17) 0.6624(3) 0.30303(14) 0.0257(4) Uani 1 1 d . . . . .
C8 C 0.37363(17) 0.5419(3) 0.26320(14) 0.0257(4) Uani 1 1 d . . . . .
C9 C 0.43418(19) 0.5786(3) 0.16251(15) 0.0309(4) Uani 1 1 d . . . . .
H9 H 0.468061 0.734529 0.165884 0.037 Uiso 1 1 calc R . . . .
C10 C 0.54850(18) 0.4250(4) 0.16392(16) 0.0362(5) Uani 1 1 d . . . . .
H10 H 0.601141 0.448777 0.109385 0.043 Uiso 1 1 calc R . . . .
C11 C 0.58155(19) 0.2605(4) 0.23446(17) 0.0354(5) Uani 1 1 d . . . . .
H11 H 0.655214 0.172839 0.226716 0.043 Uiso 1 1 calc R . . . .
C12 C 0.51041(18) 0.2029(3) 0.32610(16) 0.0321(4) Uani 1 1 d . . . . .
H12A H 0.470060 0.054109 0.311919 0.039 Uiso 1 1 calc R . . . .
H12B H 0.573348 0.196750 0.397671 0.039 Uiso 1 1 calc R . . . .
C13 C 0.0370(2) 0.7046(4) 0.65102(18) 0.0362(5) Uani 1 1 d . . . . .
H13A H -0.032115 0.701728 0.584427 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.093161 0.834441 0.648096 0.054 Uiso 1 1 calc GR . . . .
H13C H -0.002472 0.713419 0.717616 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.3339(2) 0.5533(4) 0.05249(15) 0.0344(4) Uani 1 1 d . . . . .
H14A H 0.269397 0.675573 0.047671 0.041 Uiso 1 1 calc R . . . .
H14B H 0.380394 0.570590 -0.010591 0.041 Uiso 1 1 calc R . . . .
C15 C 0.2605(2) 0.3339(4) 0.03914(16) 0.0336(4) Uani 1 1 d . . . . .
H15A H 0.205236 0.323052 0.096567 0.040 Uiso 1 1 calc R . . . .
H15B H 0.324246 0.209979 0.051226 0.040 Uiso 1 1 calc R . . . .
C16 C 0.1743(2) 0.3104(4) -0.07619(17) 0.0429(5) Uani 1 1 d . . . . .
H16A H 0.114864 0.440148 -0.089842 0.051 Uiso 1 1 calc R . . . .
H16B H 0.230661 0.312944 -0.132997 0.051 Uiso 1 1 calc R . . . .
C17 C 0.0936(3) 0.1009(5) -0.0905(2) 0.0570(7) Uani 1 1 d . . . . .
H17A H 0.036999 0.100713 -0.164306 0.085 Uiso 1 1 calc GR . . . .
H17B H 0.039554 0.094300 -0.033016 0.085 Uiso 1 1 calc GR . . . .
H17C H 0.151676 -0.028629 -0.083528 0.085 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
Cl1 C7 1.7239(19) . ?
O1 C2 1.373(2) . ?
O1 C13 1.429(3) . ?
N1 C5 1.383(2) . ?
N1 C8 1.377(2) . ?
N1 C12 1.452(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.406(2) . ?
C2 C3 1.409(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.407(2) . ?
C6 C7 1.426(2) . ?
C7 C8 1.372(3) . ?
C8 C9 1.501(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.504(3) . ?
C9 C14 1.547(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.315(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.495(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.518(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.506(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C2 O1 C13 117.02(15) . . ?
C5 N1 C12 124.70(16) . . ?
C8 N1 C5 109.07(15) . . ?
C8 N1 C12 126.11(16) . . ?
C2 C1 H1 121.3 . . ?
C2 C1 C6 117.46(18) . . ?
C6 C1 H1 121.3 . . ?
O1 C2 C1 124.65(17) . . ?
O1 C2 C3 113.85(16) . . ?
C1 C2 C3 121.50(17) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.57(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.12(17) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 129.55(17) . . ?
N1 C5 C6 108.49(15) . . ?
C4 C5 C6 121.95(16) . . ?
C1 C6 C5 120.38(16) . . ?
C1 C6 C7 134.22(18) . . ?
C5 C6 C7 105.37(15) . . ?
C6 C7 Cl1 125.69(14) . . ?
C8 C7 Cl1 125.24(14) . . ?
C8 C7 C6 109.06(17) . . ?
N1 C8 C9 121.61(16) . . ?
C7 C8 N1 108.01(16) . . ?
C7 C8 C9 130.38(17) . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C10 110.72(16) . . ?
C8 C9 C14 112.30(15) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C14 110.65(16) . . ?
C14 C9 H9 107.7 . . ?
C9 C10 H10 117.3 . . ?
C11 C10 C9 125.34(18) . . ?
C11 C10 H10 117.3 . . ?
C10 C11 H11 118.0 . . ?
C10 C11 C12 124.08(18) . . ?
C12 C11 H11 118.0 . . ?
N1 C12 C11 111.22(17) . . ?
N1 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 108.5 . . ?
C9 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C9 115.00(16) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.06(17) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.7(2) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
