# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_C13H8ClFN2O2-EC3
_database_code_depnum_ccdc_archive 'CCDC 1840963'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Cl F N2 O2'
_chemical_formula_weight         278.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8145(15)
_cell_length_b                   12.348(4)
_cell_length_c                   13.349(5)
_cell_angle_alpha                71.50(3)
_cell_angle_beta                 89.83(5)
_cell_angle_gamma                89.58(5)
_cell_volume                     596.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6279
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   0.969
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6279
_diffrn_reflns_av_unetI/netI     0.1220
_diffrn_reflns_av_R_equivalents  0.10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.609
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2701
_reflns_number_gt                2015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+2.2947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2701
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2645
_refine_ls_wR_factor_gt          0.2444
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.0090(4) 0.92841(11) -0.16166(10) 0.0358(4) Uani 1 1 d . . . . .
F F 0.8712(9) 0.0787(3) 0.5744(3) 0.0418(8) Uani 1 1 d . . . . .
O1 O 1.1187(11) 0.2339(4) 0.6499(3) 0.0425(10) Uani 1 1 d . . . . .
O2 O 0.8337(11) 0.3946(3) 0.6034(3) 0.0387(9) Uani 1 1 d . . . . .
N1 N 0.9210(11) 0.3036(4) 0.5903(3) 0.0280(9) Uani 1 1 d . . . . .
N2 N 0.4288(11) 0.4412(3) 0.2286(3) 0.0254(9) Uani 1 1 d . . . . .
C1 C 0.7873(12) 0.2799(4) 0.4962(4) 0.0239(10) Uani 1 1 d . . . . .
C2 C 0.6730(12) 0.3720(4) 0.4117(4) 0.0231(9) Uani 1 1 d . . . . .
H8 H 0.678661 0.445534 0.416355 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5489(12) 0.3538(4) 0.3193(4) 0.0241(10) Uani 1 1 d . . . . .
C4 C 0.5380(13) 0.2417(4) 0.3154(4) 0.0258(10) Uani 1 1 d . . . . .
H6 H 0.455121 0.228391 0.254911 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6515(13) 0.1489(4) 0.4021(4) 0.0293(11) Uani 1 1 d . . . . .
H7 H 0.642265 0.074785 0.399028 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7754(13) 0.1691(4) 0.4907(4) 0.0285(10) Uani 1 1 d . . . . .
C7 C 0.5189(12) 0.5443(4) 0.2129(3) 0.0230(9) Uani 1 1 d . . . . .
H5 H 0.669504 0.561059 0.260610 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3894(12) 0.6387(4) 0.1203(4) 0.0253(10) Uani 1 1 d . . . . .
C9 C 0.2376(12) 0.6155(4) 0.0344(4) 0.0238(9) Uani 1 1 d . . . . .
H2 H 0.214683 0.540129 0.035594 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1203(13) 0.7035(4) -0.0532(4) 0.0266(10) Uani 1 1 d . . . . .
H1 H 0.021890 0.688243 -0.110863 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1549(13) 0.8157(4) -0.0516(4) 0.0282(10) Uani 1 1 d . . . . .
C12 C 0.2957(13) 0.8410(4) 0.0337(4) 0.0308(11) Uani 1 1 d . . . . .
H3 H 0.308753 0.916176 0.033657 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4183(13) 0.7512(4) 0.1204(4) 0.0274(10) Uani 1 1 d . . . . .
H4 H 0.518712 0.766678 0.177734 0.033 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
Cl1 C11 1.761(5) . ?
F C6 1.355(5) . ?
O1 N1 1.225(5) . ?
O2 N1 1.234(6) . ?
N1 C1 1.471(6) . ?
N2 C7 1.274(6) . ?
N2 C3 1.417(6) . ?
C1 C2 1.392(6) . ?
C1 C6 1.394(7) . ?
C2 C3 1.406(7) . ?
C2 H8 0.9300 . ?
C3 C4 1.402(7) . ?
C4 C5 1.412(6) . ?
C4 H6 0.9300 . ?
C5 C6 1.370(7) . ?
C5 H7 0.9300 . ?
C7 C8 1.487(6) . ?
C7 H5 0.9300 . ?
C8 C13 1.395(7) . ?
C8 C9 1.396(7) . ?
C9 C10 1.392(6) . ?
C9 H2 0.9300 . ?
C10 C11 1.400(7) . ?
C10 H1 0.9300 . ?
C11 C12 1.384(7) . ?
C12 C13 1.403(7) . ?
C12 H3 0.9300 . ?
C13 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 123.5(4) . . ?
O1 N1 C1 118.7(4) . . ?
O2 N1 C1 117.8(4) . . ?
C7 N2 C3 120.1(4) . . ?
C2 C1 C6 120.5(4) . . ?
C2 C1 N1 117.9(4) . . ?
C6 C1 N1 121.6(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H8 120.0 . . ?
C3 C2 H8 120.0 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 N2 116.7(4) . . ?
C2 C3 N2 124.7(4) . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H6 119.6 . . ?
C5 C4 H6 119.6 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H7 120.3 . . ?
C4 C5 H7 120.3 . . ?
F C6 C5 118.5(4) . . ?
F C6 C1 120.7(4) . . ?
C5 C6 C1 120.7(4) . . ?
N2 C7 C8 121.6(4) . . ?
N2 C7 H5 119.2 . . ?
C8 C7 H5 119.2 . . ?
C13 C8 C9 120.1(4) . . ?
C13 C8 C7 119.3(4) . . ?
C9 C8 C7 120.7(4) . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H2 119.5 . . ?
C8 C9 H2 119.5 . . ?
C9 C10 C11 118.0(4) . . ?
C9 C10 H1 121.0 . . ?
C11 C10 H1 121.0 . . ?
C12 C11 C10 122.3(4) . . ?
C12 C11 Cl1 119.0(4) . . ?
C10 C11 Cl1 118.7(4) . . ?
C11 C12 C13 118.9(5) . . ?
C11 C12 H3 120.6 . . ?
C13 C12 H3 120.6 . . ?
C8 C13 C12 119.9(5) . . ?
C8 C13 H4 120.1 . . ?
C12 C13 H4 120.1 . . ?

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
O1 N1 C1 C2 -157.4(5) . . . . ?
O2 N1 C1 C2 20.8(7) . . . . ?
O1 N1 C1 C6 22.3(7) . . . . ?
O2 N1 C1 C6 -159.5(5) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
N1 C1 C2 C3 178.9(4) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C1 C2 C3 N2 -179.5(4) . . . . ?
C7 N2 C3 C4 -160.0(5) . . . . ?
C7 N2 C3 C2 20.5(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
N2 C3 C4 C5 -179.9(4) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C4 C5 C6 F 177.7(4) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C2 C1 C6 F -177.0(4) . . . . ?
N1 C1 C6 F 3.3(7) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
N1 C1 C6 C5 -179.7(5) . . . . ?
C3 N2 C7 C8 -178.1(4) . . . . ?
N2 C7 C8 C13 163.5(5) . . . . ?
N2 C7 C8 C9 -16.0(7) . . . . ?
C13 C8 C9 C10 1.4(7) . . . . ?
C7 C8 C9 C10 -179.1(4) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C9 C10 C11 Cl1 179.9(4) . . . . ?
C10 C11 C12 C13 2.1(8) . . . . ?
Cl1 C11 C12 C13 -178.7(4) . . . . ?
C9 C8 C13 C12 -0.2(7) . . . . ?
C7 C8 C13 C12 -179.7(4) . . . . ?
C11 C12 C13 C8 -1.5(8) . . . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_C16H15Cl2NO3-EC4
_database_code_depnum_ccdc_archive 'CCDC 1840966'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Cl2 N O3'
_chemical_formula_weight         340.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

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

_cell_length_a                   27.733
_cell_length_b                   4.024
_cell_length_c                   13.705
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1529.4
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3167
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.471

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   0.984
_exptl_transmission_factor_max   0.991
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14617
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.469
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3489
_reflns_number_gt                3167
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.1702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27984(4) 0.0009(3) 0.44048(10) 0.0358(3) Uani 1 1 d . . . . .
Cl2 Cl 0.18017(4) 0.3403(4) 0.38501(9) 0.0398(3) Uani 1 1 d . . . . .
O1 O 0.07783(12) -0.0035(8) 1.1587(2) 0.0273(7) Uani 1 1 d . . . . .
O3 O -0.02556(10) 0.5426(8) 0.9419(2) 0.0261(7) Uani 1 1 d . . . . .
O2 O -0.00339(11) 0.3277(8) 1.1215(2) 0.0241(7) Uani 1 1 d . . . . .
C4 C 0.09444(14) 0.1831(10) 0.8973(3) 0.0203(8) Uani 1 1 d . . . . .
C5 C 0.05168(15) 0.3538(10) 0.8777(3) 0.0223(8) Uani 1 1 d . . . . .
H5 H 0.045651 0.440166 0.815909 0.027 Uiso 1 1 calc R U . . .
N1 N 0.13258(13) 0.2992(9) 0.7420(3) 0.0236(8) Uani 1 1 d . . . . .
C13 C 0.15964(16) 0.3029(11) 0.5763(3) 0.0238(9) Uani 1 1 d . . . . .
H13 H 0.130455 0.401957 0.559851 0.029 Uiso 1 1 calc R U . . .
C6 C 0.01843(14) 0.3917(10) 0.9523(3) 0.0201(8) Uani 1 1 d . . . . .
C1 C 0.02804(16) 0.2698(11) 1.0463(3) 0.0213(9) Uani 1 1 d . . . . .
C2 C 0.07136(15) 0.1021(11) 1.0647(3) 0.0212(9) Uani 1 1 d . . . . .
C10 C 0.24730(17) 0.0209(11) 0.6250(4) 0.0283(10) Uani 1 1 d . . . . .
H10 H 0.276779 -0.074278 0.641267 0.034 Uiso 1 1 calc R U . . .
C3 C 0.10413(15) 0.0536(11) 0.9898(3) 0.0212(9) Uani 1 1 d . . . . .
H3 H 0.132423 -0.064400 1.001016 0.025 Uiso 1 1 calc R U . . .
C12 C 0.19317(17) 0.2343(12) 0.5043(3) 0.0254(9) Uani 1 1 d . . . . .
C11 C 0.23727(16) 0.0943(12) 0.5285(3) 0.0260(10) Uani 1 1 d . . . . .
C16 C -0.03748(17) 0.6666(12) 0.8472(3) 0.0266(10) Uani 1 1 d . . . . .
H16A H -0.068926 0.766190 0.848984 0.040 Uiso 1 1 calc R U . . .
H16B H -0.014143 0.830137 0.827943 0.040 Uiso 1 1 calc R U . . .
H16C H -0.037385 0.486919 0.801163 0.040 Uiso 1 1 calc R U . . .
C14 C 0.12203(17) -0.1687(12) 1.1803(4) 0.0309(10) Uani 1 1 d . . . . .
H14A H 0.122515 -0.230792 1.247874 0.046 Uiso 1 1 calc R U . . .
H14B H 0.124800 -0.364156 1.140497 0.046 Uiso 1 1 calc R U . . .
H14C H 0.148558 -0.022273 1.166888 0.046 Uiso 1 1 calc R U . . .
C9 C 0.21410(16) 0.0871(13) 0.6973(4) 0.0270(9) Uani 1 1 d . . . . .
H9 H 0.221446 0.040587 0.762038 0.032 Uiso 1 1 calc R U . . .
C8 C 0.16935(16) 0.2244(11) 0.6730(3) 0.0223(9) Uani 1 1 d . . . . .
C15 C -0.04524(17) 0.1161(12) 1.1211(4) 0.0321(11) Uani 1 1 d . . . . .
H15A H -0.065488 0.170634 1.175628 0.048 Uiso 1 1 calc R U . . .
H15B H -0.062846 0.148288 1.061555 0.048 Uiso 1 1 calc R U . . .
H15C H -0.035299 -0.111880 1.125912 0.048 Uiso 1 1 calc R U . . .
C7 C 0.13077(15) 0.1266(11) 0.8204(3) 0.0224(9) Uani 1 1 d . . . . .
H7 H 0.153004 -0.046100 0.833302 0.046(17) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.730(5) . ?
Cl2 C12 1.728(5) . ?
O1 C2 1.368(5) . ?
O1 C14 1.426(6) . ?
O3 C6 1.370(5) . ?
O3 C16 1.428(5) . ?
O2 C1 1.370(5) . ?
O2 C15 1.440(5) . ?
C4 C5 1.397(6) . ?
C4 C3 1.397(6) . ?
C4 C7 1.475(6) . ?
C5 C6 1.386(6) . ?
N1 C7 1.281(6) . ?
N1 C8 1.423(5) . ?
C13 C12 1.383(6) . ?
C13 C8 1.389(6) . ?
C6 C1 1.403(6) . ?
C1 C2 1.401(6) . ?
C2 C3 1.385(6) . ?
C10 C9 1.378(7) . ?
C10 C11 1.382(7) . ?
C12 C11 1.387(6) . ?
C9 C8 1.398(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C14 116.9(4) . . ?
C6 O3 C16 117.1(3) . . ?
C1 O2 C15 114.2(3) . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 C7 121.2(4) . . ?
C3 C4 C7 117.3(4) . . ?
C6 C5 C4 118.5(4) . . ?
C7 N1 C8 118.1(4) . . ?
C12 C13 C8 120.3(4) . . ?
O3 C6 C5 124.3(4) . . ?
O3 C6 C1 114.8(4) . . ?
C5 C6 C1 120.9(4) . . ?
O2 C1 C2 119.4(4) . . ?
O2 C1 C6 120.7(4) . . ?
C2 C1 C6 119.8(4) . . ?
O1 C2 C3 124.6(4) . . ?
O1 C2 C1 115.6(4) . . ?
C3 C2 C1 119.8(4) . . ?
C9 C10 C11 120.7(4) . . ?
C2 C3 C4 119.6(4) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 Cl2 119.0(4) . . ?
C11 C12 Cl2 120.7(4) . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 Cl1 118.9(4) . . ?
C12 C11 Cl1 121.6(4) . . ?
C10 C9 C8 119.9(4) . . ?
C13 C8 C9 119.2(4) . . ?
C13 C8 N1 116.5(4) . . ?
C9 C8 N1 124.2(4) . . ?
N1 C7 C4 122.8(4) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_CHNClI-EC2
_database_code_depnum_ccdc_archive 'CCDC 1840965'
_audit_update_record             
;
2018-05-22 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Cl2 I N'
_chemical_formula_weight         376.00

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.100(3)
_cell_length_b                   22.199(14)
_cell_length_c                   14.223(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.954(5)
_cell_angle_gamma                90
_cell_volume                     1284.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2710
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.481

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   0.901
_exptl_transmission_factor_max   0.944
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.883
_shelx_estimated_absorpt_T_min   0.392
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13081
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2945
_reflns_number_gt                2710
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.7831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2945
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.60389(6) 0.72159(2) 0.57065(2) 0.02903(13) Uani 1 1 d . . . . .
C1 C 0.4051(9) 0.79908(16) 0.5008(3) 0.0221(7) Uani 1 1 d . . . . .
C2 C 0.4567(10) 0.85495(18) 0.5437(3) 0.0246(8) Uani 1 1 d . . . . .
H2 H 0.572520 0.858263 0.603888 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2364(10) 0.79350(18) 0.4106(3) 0.0256(8) Uani 1 1 d . . . . .
H6 H 0.207571 0.755821 0.382245 0.031 Uiso 1 1 calc R U . . .
N1 N 0.0460(9) 0.95529(15) 0.3584(2) 0.0233(7) Uani 1 1 d . . . . .
C4 C 0.1544(9) 0.90118(17) 0.4057(3) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.1114(10) 0.84449(18) 0.3633(3) 0.0258(8) Uani 1 1 d . . . . .
H5 H -0.001985 0.841027 0.302806 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3318(10) 0.90601(17) 0.4949(3) 0.0243(8) Uani 1 1 d . . . . .
H3 H 0.367801 0.943792 0.522500 0.029 Uiso 1 1 calc R U . . .
C7 C -0.2052(10) 0.95273(17) 0.2959(3) 0.0214(7) Uani 1 1 d . . . . .
Cl2 Cl -0.7078(3) 0.93067(4) 0.12057(7) 0.0303(2) Uani 1 1 d . . . . .
C8 C -0.3165(9) 1.00553(17) 0.2386(3) 0.0208(7) Uani 1 1 d . . . . .
C13 C -0.1891(9) 1.06241(17) 0.2629(3) 0.0212(7) Uani 1 1 d . . . . .
H13 H -0.040312 1.067343 0.317121 0.025 Uiso 1 1 calc R U . . .
C12 C -0.2847(10) 1.11157(17) 0.2061(3) 0.0231(7) Uani 1 1 d . . . . .
C10 C -0.6317(10) 1.04978(18) 0.0990(3) 0.0252(8) Uani 1 1 d . . . . .
H10 H -0.778833 1.045216 0.044399 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl -0.1255(3) 1.18199(4) 0.23860(7) 0.0317(2) Uani 1 1 d . . . . .
C11 C -0.5019(10) 1.10559(19) 0.1246(3) 0.0262(8) Uani 1 1 d . . . . .
H11 H -0.560448 1.139062 0.086951 0.031 Uiso 1 1 calc R U . . .
C9 C -0.5386(9) 1.00036(17) 0.1565(3) 0.0217(7) Uani 1 1 d . . . . .
H7 H -0.319(13) 0.920(2) 0.293(4) 0.039(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.101(4) . ?
C1 C6 1.387(6) . ?
C1 C2 1.387(5) . ?
C2 C3 1.394(5) . ?
C6 C5 1.383(6) . ?
N1 C7 1.277(5) . ?
N1 C4 1.421(5) . ?
C4 C3 1.389(5) . ?
C4 C5 1.397(5) . ?
C7 C8 1.469(5) . ?
Cl2 C9 1.746(4) . ?
C8 C13 1.394(6) . ?
C8 C9 1.395(5) . ?
C13 C12 1.386(5) . ?
C12 C11 1.381(6) . ?
C12 Cl1 1.735(4) . ?
C10 C11 1.379(6) . ?
C10 C9 1.393(5) . ?

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
C6 C1 C2 121.3(3) . . ?
C6 C1 I1 119.1(3) . . ?
C2 C1 I1 119.6(3) . . ?
C1 C2 C3 118.7(3) . . ?
C5 C6 C1 119.4(4) . . ?
C7 N1 C4 118.1(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 N1 117.8(3) . . ?
C5 C4 N1 122.7(3) . . ?
C6 C5 C4 120.4(4) . . ?
C4 C3 C2 120.8(3) . . ?
N1 C7 C8 121.4(4) . . ?
C13 C8 C9 118.0(4) . . ?
C13 C8 C7 120.2(4) . . ?
C9 C8 C7 121.8(4) . . ?
C12 C13 C8 119.9(4) . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 Cl1 119.6(3) . . ?
C13 C12 Cl1 118.9(3) . . ?
C11 C10 C9 118.9(4) . . ?
C10 C11 C12 119.8(4) . . ?
C10 C9 C8 122.0(4) . . ?
C10 C9 Cl2 117.1(3) . . ?
C8 C9 Cl2 120.9(3) . . ?

_refine_diff_density_max         0.786
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.163

####################################################################### 
# 
# 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_C15H9N-EC1
_database_code_depnum_ccdc_archive 'CCDC 1840964'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 N'
_chemical_formula_weight         203.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   3.8727(9)
_cell_length_b                   15.111(4)
_cell_length_c                   17.132(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1002.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2283
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Acicular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   0.997
_exptl_transmission_factor_max   0.998
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10559
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_av_R_equivalents  0.1645
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.797
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2266
_reflns_number_gt                1879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.23(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -10(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2097
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.184
_refine_ls_shift/su_mean         0.005

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
N1 N -0.0564(11) -0.0731(2) 0.1628(2) 0.0430(10) Uani 1 1 d . . . . .
C049 C 0.4077(9) 0.2115(2) 0.2422(2) 0.0252(8) Uani 1 1 d . . . . .
C050 C 0.3061(9) 0.1346(2) 0.1992(2) 0.0244(9) Uani 1 1 d . . . . .
C051 C 0.1411(10) 0.0651(2) 0.2398(2) 0.0251(8) Uani 1 1 d . . . . .
C052 C 0.0781(10) 0.0691(2) 0.3209(2) 0.0253(8) Uani 1 1 d . . . . .
C053 C -0.1435(12) 0.0074(3) 0.4409(2) 0.0356(10) Uani 1 1 d . . . . .
H053 H -0.253481 -0.038218 0.467472 0.043 Uiso 1 1 calc R U . . .
C054 C 0.1873(10) 0.1467(2) 0.3624(2) 0.0269(9) Uani 1 1 d . . . . .
C055 C 0.0321(11) -0.0114(2) 0.1972(2) 0.0283(9) Uani 1 1 d . . . . .
C056 C 0.5670(10) 0.2828(2) 0.2016(2) 0.0302(9) Uani 1 1 d . . . . .
H056 H 0.633158 0.333282 0.228762 0.036 Uiso 1 1 calc R U . . .
C057 C 0.3475(10) 0.2152(2) 0.3220(2) 0.0279(9) Uani 1 1 d . . . . .
H057 H 0.416613 0.265298 0.349469 0.034 Uiso 1 1 calc R U . . .
C058 C 0.1268(11) 0.1505(3) 0.4446(2) 0.0336(10) Uani 1 1 d . . . . .
H058 H 0.199568 0.199802 0.472641 0.040 Uiso 1 1 calc R U . . .
C059 C -0.0893(11) 0.0002(3) 0.3626(2) 0.0312(9) Uani 1 1 d . . . . .
H059 H -0.162478 -0.050223 0.336231 0.037 Uiso 1 1 calc R U . . .
C060 C -0.0342(12) 0.0838(3) 0.4824(2) 0.0391(11) Uani 1 1 d . . . . .
H060 H -0.073546 0.087873 0.535857 0.047 Uiso 1 1 calc R U . . .
C061 C 0.3731(10) 0.1313(2) 0.1178(2) 0.0281(9) Uani 1 1 d . . . . .
H061 H 0.310699 0.081634 0.089037 0.034 Uiso 1 1 calc R U . . .
C062 C 0.5285(10) 0.2010(3) 0.0818(2) 0.0311(9) Uani 1 1 d . . . . .
H062 H 0.573155 0.197888 0.028540 0.037 Uiso 1 1 calc R U . . .
C064 C 0.6234(11) 0.2777(3) 0.1233(2) 0.0322(9) Uani 1 1 d . . . . .
H064 H 0.724697 0.325010 0.097107 0.039 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
N1 C055 1.154(5) . ?
C049 C057 1.389(5) . ?
C049 C056 1.424(5) . ?
C049 C050 1.430(5) . ?
C050 C061 1.421(5) . ?
C050 C051 1.412(5) . ?
C051 C052 1.411(5) . ?
C051 C055 1.431(5) . ?
C052 C059 1.419(5) . ?
C052 C054 1.435(5) . ?
C053 C059 1.362(6) . ?
C053 C060 1.420(6) . ?
C053 H053 0.9300 . ?
C054 C057 1.391(5) . ?
C054 C058 1.430(5) . ?
C056 C064 1.361(6) . ?
C056 H056 0.9300 . ?
C057 H057 0.9300 . ?
C058 C060 1.350(6) . ?
C058 H058 0.9300 . ?
C059 H059 0.9300 . ?
C060 H060 0.9300 . ?
C061 C062 1.360(5) . ?
C061 H061 0.9300 . ?
C062 C064 1.409(6) . ?
C062 H062 0.9300 . ?
C064 H064 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C057 C049 C056 121.5(3) . . ?
C057 C049 C050 119.6(3) . . ?
C056 C049 C050 118.9(3) . . ?
C061 C050 C051 122.7(3) . . ?
C061 C050 C049 118.9(3) . . ?
C051 C050 C049 118.4(3) . . ?
C050 C051 C052 122.0(3) . . ?
C050 C051 C055 118.9(3) . . ?
C052 C051 C055 119.1(3) . . ?
C051 C052 C059 122.8(3) . . ?
C051 C052 C054 118.2(3) . . ?
C059 C052 C054 119.0(3) . . ?
C059 C053 C060 120.8(4) . . ?
C059 C053 H053 119.6 . . ?
C060 C053 H053 119.6 . . ?
C057 C054 C052 119.6(3) . . ?
C057 C054 C058 122.2(4) . . ?
C052 C054 C058 118.2(3) . . ?
N1 C055 C051 179.9(5) . . ?
C064 C056 C049 120.6(4) . . ?
C064 C056 H056 119.7 . . ?
C049 C056 H056 119.7 . . ?
C054 C057 C049 122.3(3) . . ?
C054 C057 H057 118.9 . . ?
C049 C057 H057 118.9 . . ?
C060 C058 C054 121.2(4) . . ?
C060 C058 H058 119.4 . . ?
C054 C058 H058 119.4 . . ?
C053 C059 C052 120.5(4) . . ?
C053 C059 H059 119.8 . . ?
C052 C059 H059 119.8 . . ?
C058 C060 C053 120.2(4) . . ?
C058 C060 H060 119.9 . . ?
C053 C060 H060 119.9 . . ?
C062 C061 C050 119.9(3) . . ?
C062 C061 H061 120.0 . . ?
C050 C061 H061 120.0 . . ?
C061 C062 C064 121.6(4) . . ?
C061 C062 H062 119.2 . . ?
C064 C062 H062 119.2 . . ?
C056 C064 C062 120.1(4) . . ?
C056 C064 H064 120.0 . . ?
C062 C064 H064 120.0 . . ?

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
C057 C049 C050 C061 -179.3(3) . . . . ?
C056 C049 C050 C061 1.1(5) . . . . ?
C057 C049 C050 C051 1.0(5) . . . . ?
C056 C049 C050 C051 -178.6(3) . . . . ?
C061 C050 C051 C052 179.7(4) . . . . ?
C049 C050 C051 C052 -0.7(5) . . . . ?
C061 C050 C051 C055 -0.9(5) . . . . ?
C049 C050 C051 C055 178.8(3) . . . . ?
C050 C051 C052 C059 179.6(4) . . . . ?
C055 C051 C052 C059 0.1(5) . . . . ?
C050 C051 C052 C054 -0.1(5) . . . . ?
C055 C051 C052 C054 -179.6(3) . . . . ?
C051 C052 C054 C057 0.6(5) . . . . ?
C059 C052 C054 C057 -179.1(3) . . . . ?
C051 C052 C054 C058 -179.4(4) . . . . ?
C059 C052 C054 C058 0.9(5) . . . . ?
C057 C049 C056 C064 -180.0(4) . . . . ?
C050 C049 C056 C064 -0.3(5) . . . . ?
C052 C054 C057 C049 -0.2(5) . . . . ?
C058 C054 C057 C049 179.7(4) . . . . ?
C056 C049 C057 C054 179.0(3) . . . . ?
C050 C049 C057 C054 -0.6(5) . . . . ?
C057 C054 C058 C060 178.9(4) . . . . ?
C052 C054 C058 C060 -1.1(6) . . . . ?
C060 C053 C059 C052 0.0(6) . . . . ?
C051 C052 C059 C053 179.9(4) . . . . ?
C054 C052 C059 C053 -0.4(6) . . . . ?
C054 C058 C060 C053 0.8(7) . . . . ?
C059 C053 C060 C058 -0.2(7) . . . . ?
C051 C050 C061 C062 179.0(4) . . . . ?
C049 C050 C061 C062 -0.6(5) . . . . ?
C050 C061 C062 C064 -0.6(6) . . . . ?
C049 C056 C064 C062 -0.9(6) . . . . ?
C061 C062 C064 C056 1.4(6) . . . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.176

