# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ogh_d49_9or7
_database_code_depnum_ccdc_archive 'CCDC 2383798'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C7 H10 N O'
_chemical_formula_sum            'C7 H10 Cl N O'
_chemical_formula_weight         159.61
_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   6.2444(3)
_cell_length_b                   9.2125(4)
_cell_length_c                   6.7656(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.855(2)
_cell_angle_gamma                90
_cell_volume                     387.81(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5662
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.284
_cell_measurement_theta_min      3.022
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1230 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9061.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8522
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         3.022
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                769
_reflns_number_total             843
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.116
_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)+(0.0254P)²+0.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0682
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.20413(7) 0.250000 0.18874(7) 0.01733(15) Uani 1 2 d S T P . .
O1 O 0.0926(2) 0.250000 0.5950(2) 0.0189(3) Uani 1 2 d S T P . .
H1 H 0.096939 0.237471 0.472379 0.028 Uiso 0.5 1 calc R U P A -1
N1 N 0.2991(2) 0.250000 0.6859(2) 0.0147(3) Uani 1 2 d S T P . .
C3 C 0.7006(3) 0.250000 0.8702(3) 0.0179(4) Uani 1 2 d S T P . .
H3 H 0.842000 0.249999 0.934183 0.021 Uiso 1 2 calc R U P . .
C2 C 0.5974(2) 0.37999(15) 0.82350(19) 0.0172(3) Uani 1 1 d . . . . .
H2 H 0.667940 0.469239 0.856130 0.021 Uiso 1 1 calc R U . . .
C1 C 0.3913(2) 0.38048(15) 0.72926(19) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.2678(2) 0.51500(16) 0.6744(2) 0.0219(3) Uani 1 1 d . . . . .
H4A H 0.224404 0.514212 0.531760 0.033 Uiso 1 1 calc R U . . .
H4B H 0.358147 0.600099 0.706967 0.033 Uiso 1 1 calc R U . . .
H4C H 0.139616 0.519169 0.748353 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
O1 H1 0.8400 . ?
O1 N1 1.3808(19) . ?
N1 C1 1.3542(15) . ?
N1 C1 1.3542(15) 4_565 ?
C3 H3 0.9500 . ?
C3 C2 1.3837(17) 4_565 ?
C3 C2 1.3837(17) . ?
C2 H2 0.9500 . ?
C2 C1 1.3868(19) . ?
C1 C4 1.4900(19) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 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
N1 O1 H1 109.5 . . ?
C1 N1 O1 117.42(8) . . ?
C1 N1 O1 117.42(8) 4_565 . ?
C1 N1 C1 125.14(16) 4_565 . ?
C2 C3 H3 120.1 4_565 . ?
C2 C3 H3 120.1 . . ?
C2 C3 C2 119.86(18) . 4_565 ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.26(13) . . ?
C1 C2 H2 119.9 . . ?
N1 C1 C2 117.24(13) . . ?
N1 C1 C4 118.86(12) . . ?
C2 C1 C4 123.90(13) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 178.99(12) . . . . ?
O1 N1 C1 C4 -0.9(2) . . . . ?
C3 C2 C1 N1 -0.2(2) . . . . ?
C3 C2 C1 C4 179.68(14) . . . . ?
C2 C3 C2 C1 -0.3(3) 4_565 . . . ?
C1 N1 C1 C2 0.7(3) 4_565 . . . ?
C1 N1 C1 C4 -179.14(11) 4_565 . . . ?

_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_OGH_D49_38
_database_code_depnum_ccdc_archive 'CCDC 2383800'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H6 N O, 1(Cl1)'
_chemical_formula_sum            'C5 H6 Cl N O'
_chemical_formula_weight         131.56
_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 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2301(13)
_cell_length_b                   7.416(2)
_cell_length_c                   11.002(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     589.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1110
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.326
_cell_measurement_theta_min      3.372
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.745207
_exptl_absorpt_correction_T_min  0.263470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1594 before and 0.0953 after correction.
 The Ratio of minimum to maximum transmission is 0.36.

Final HKLF 4 output contains 6410 reflections, Rint = 0.1953
 (2497 with I > 3sig(I), Rint = 0.0809)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            674
_diffrn_reflns_point_group_measured_fraction_full 0.603
_diffrn_reflns_point_group_measured_fraction_max 0.603
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                621
_reflns_number_total             674
_reflns_special_details          
;
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         1.145
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         674
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0933
_refine_ls_restrained_S_all      1.093
_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)+(0.1893P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2335
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.98143
 0.01857
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(Cl1) = Uanis(Cl2) = Uanis(Cl3)
3. Others
 Fixed Sof: Cl1(0.89) Cl2(0.06) Cl3(0.05)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3), C1(H1A)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.1198(8) 0.2556(9) 0.2920(5) 0.0325(16) Uani 1 1 d . . . . .
H1 H 1.176692 0.332668 0.250371 0.049 Uiso 1 1 calc R U . . .
N1 N 0.9428(9) 0.3055(9) 0.3039(5) 0.0207(15) Uani 1 1 d . . . . .
C2 C 0.7113(12) 0.4259(10) 0.4280(7) 0.0268(19) Uani 1 1 d . . . . .
H2 H 0.673171 0.477794 0.502824 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8182(13) 0.2741(11) 0.2132(7) 0.025(2) Uani 1 1 d . . . . .
H5 H 0.857977 0.220893 0.139105 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6400(12) 0.3182(12) 0.2282(7) 0.0249(19) Uani 1 1 d . . . . .
H4 H 0.553798 0.297182 0.164588 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5812(11) 0.3943(11) 0.3365(6) 0.0246(19) Uani 1 1 d . . . . .
H3 H 0.454823 0.424451 0.348406 0.030 Uiso 1 1 calc R U . . .
C1 C 0.8908(12) 0.3831(12) 0.4106(7) 0.029(2) Uani 1 1 d . . . . .
H1A H 0.979658 0.406827 0.472134 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2796(3) 0.5819(3) 0.56356(16) 0.0162(8) Uani 0.89 1 d . U P A 1
Cl2 Cl 0.165(5) 0.591(4) 0.564(2) 0.0162(8) Uani 0.06 1 d . U P B 2
Cl3 Cl 0.392(6) 0.597(5) 0.561(3) 0.0162(8) Uani 0.05 1 d . U P C 3


_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 H1 0.8400 . ?
O1 N1 1.339(9) . ?
N1 C5 1.365(10) . ?
N1 C1 1.361(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(11) . ?
C2 C1 1.349(12) . ?
C5 H5 0.9500 . ?
C5 C4 1.340(13) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(11) . ?
C3 H3 0.9500 . ?
C1 H1A 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
N1 O1 H1 109.5 . . ?
O1 N1 C5 120.8(6) . . ?
O1 N1 C1 117.8(6) . . ?
C1 N1 C5 121.4(7) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(8) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 N1 120.2(7) . . ?
C4 C5 H5 119.9 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0(7) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(7) . . ?
C4 C3 H3 120.6 . . ?
N1 C1 H1A 120.4 . . ?
C2 C1 N1 119.2(7) . . ?
C2 C1 H1A 120.4 . . ?

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 C5 C4 177.3(7) . . . . ?
O1 N1 C1 C2 -176.4(7) . . . . ?
N1 C5 C4 C3 -0.6(12) . . . . ?
C5 N1 C1 C2 1.6(11) . . . . ?
C5 C4 C3 C2 0.8(12) . . . . ?
C3 C2 C1 N1 -1.3(12) . . . . ?
C1 N1 C5 C4 -0.6(11) . . . . ?
C1 C2 C3 C4 0.1(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.98143
2 0.01857

####################################################################### 
# 
# 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_OGH_D49_9
_database_code_depnum_ccdc_archive 'CCDC 2383799'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl2, 0.5(C14 H18 N2 O2)'
_chemical_formula_sum            'C7 H9 Cl2 N O'
_chemical_formula_weight         194.05
_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   6.9789(7)
_cell_length_b                   7.1228(6)
_cell_length_c                   8.6438(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.072(4)
_cell_angle_gamma                90
_cell_volume                     429.40(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4108
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.306
_cell_measurement_theta_min      2.358
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.779
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8574.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.358
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                795
_reflns_number_total             950
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.261
_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)+1.0014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: H7A(0.5) H7B(0.5) H7C(0.5) H6A(0.5) H6B(0.5) H6C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined with everything fixed:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.10204(8) 0.39399(9) 0.19966(7) 0.01773(19) Uani 1 1 d . . . . .
O1 O 0.1562(3) 0.750000 0.2174(3) 0.0176(6) Uani 1 2 d S T P . .
N1 N 0.3405(4) 0.750000 0.2563(3) 0.0140(6) Uani 1 2 d S T P . .
C1 C 0.4712(5) 0.750000 0.1416(4) 0.0164(7) Uani 1 2 d S T P . .
C5 C 0.3967(5) 0.750000 0.4094(4) 0.0163(7) Uani 1 2 d S T P . .
C2 C 0.6643(5) 0.750000 0.1831(4) 0.0188(8) Uani 1 2 d S T P . .
H2 H 0.756318 0.750000 0.104737 0.023 Uiso 1 2 calc R U P . .
C4 C 0.5895(5) 0.750000 0.4494(4) 0.0208(8) Uani 1 2 d S T P . .
H4 H 0.629733 0.750000 0.555565 0.025 Uiso 1 2 calc R U P . .
C3 C 0.7255(5) 0.750000 0.3367(5) 0.0209(8) Uani 1 2 d S T P . .
H3 H 0.858391 0.750000 0.364580 0.025 Uiso 1 2 calc R U P . .
C7 C 0.2410(6) 0.750000 0.5232(4) 0.0233(8) Uani 1 2 d S T P . .
H7A H 0.155646 0.857063 0.502751 0.035 Uiso 0.5 1 calc . U P A -1
H7B H 0.297538 0.759897 0.628382 0.035 Uiso 0.5 1 calc . U P B -1
H7C H 0.167653 0.633040 0.513382 0.035 Uiso 0.5 1 calc . U P C -1
C6 C 0.3924(5) 0.750000 -0.0208(4) 0.0216(8) Uani 1 2 d S T P . .
H6A H 0.324260 0.631873 -0.041573 0.032 Uiso 0.5 1 calc . U P D -1
H6B H 0.497657 0.762646 -0.092110 0.032 Uiso 0.5 1 calc . U P E -1
H6C H 0.303472 0.855481 -0.035514 0.032 Uiso 0.5 1 calc . U P F -1


_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 Cl1 2.0513(13) 4_565 ?
O1 N1 1.318(4) . ?
N1 C1 1.372(5) . ?
N1 C5 1.367(5) . ?
C1 C2 1.382(5) . ?
C1 C6 1.488(5) . ?
C5 C4 1.377(5) . ?
C5 C7 1.492(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(5) . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
O1 N1 C1 119.0(3) . . ?
O1 N1 C5 119.4(3) . . ?
C5 N1 C1 121.7(3) . . ?
N1 C1 C2 118.7(3) . . ?
N1 C1 C6 116.7(3) . . ?
C2 C1 C6 124.7(3) . . ?
N1 C5 C4 119.1(3) . . ?
N1 C5 C7 116.6(3) . . ?
C4 C5 C7 124.3(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 180.000(0) . . . . ?
O1 N1 C1 C6 0.000(0) . . . . ?
O1 N1 C5 C4 180.000(0) . . . . ?
O1 N1 C5 C7 0.000(1) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
N1 C5 C4 C3 0.000(1) . . . . ?
C1 N1 C5 C4 0.000(1) . . . . ?
C1 N1 C5 C7 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C5 N1 C1 C2 0.000(0) . . . . ?
C5 N1 C1 C6 180.000(0) . . . . ?
C5 C4 C3 C2 0.000(1) . . . . ?
C7 C5 C4 C3 180.000(1) . . . . ?
C6 C1 C2 C3 180.000(0) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT431_OGH_D49_9           
;
PROBLEM: Short Inter HL..A Contact Cl1 ..O1 . 2.57 Ang.
RESPONSE: Coordination of chlorine to N-Oxide (halogen bonding)
;
####################################################################### 
# 
# 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_OGH_D49_34
_database_code_depnum_ccdc_archive 'CCDC 2383801'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl3, C14 H19 N2 O4'
_chemical_formula_sum            'C14 H19 Cl3 N2 O4'
_chemical_formula_weight         385.66
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   11.8112(5)
_cell_length_b                   8.9258(3)
_cell_length_c                   17.6828(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.1780(10)
_cell_angle_gamma                90
_cell_volume                     1771.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.675911
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1343 before and 0.0629 after correction.
 The Ratio of minimum to maximum transmission is 0.91.

Final HKLF 4 output contains 73828 reflections, Rint = 0.0904
 (37887 with I > 3sig(I), Rint = 0.0766)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.677
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.182
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2205
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_min         2.916
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1955
_reflns_number_total             2205
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.119
_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)+(0.0426P)²+2.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          Twin
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4)
1.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cl2 Cl 0.500000 0.40252(6) 0.250000 0.02694(14) Uani 1 2 d S T P . .
Cl3 Cl 0.500000 0.66079(6) 0.250000 0.03308(15) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 0.14779(7) 0.250000 0.03708(16) Uani 1 2 d S T P . .
O2 O 0.61122(9) 0.11530(11) 0.52969(6) 0.0228(2) Uani 1 1 d . . . . .
O1 O 0.65878(10) 0.71873(11) 0.51373(7) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.65499(10) 0.56659(14) 0.52035(8) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.61055(12) 0.48556(17) 0.45283(8) 0.0210(3) Uani 1 1 d . . . . .
H1A H 0.588367 0.534618 0.402661 0.025 Uiso 1 1 calc R U . . .
C5 C 0.68909(12) 0.50295(17) 0.59332(9) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.59735(12) 0.33418(16) 0.45619(9) 0.0206(3) Uani 1 1 d . . . . .
H2 H 0.567524 0.277156 0.408745 0.025 Uiso 1 1 calc R U . . .
C3 C 0.62853(12) 0.26411(15) 0.53080(8) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.67497(12) 0.34989(16) 0.59904(8) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.697126 0.303258 0.649862 0.025 Uiso 1 1 calc R U . . .
C6 C 0.73940(15) 0.60268(18) 0.66342(10) 0.0299(3) Uani 1 1 d . . . . .
H6A H 0.808804 0.655985 0.657693 0.045 Uiso 1 1 calc R U . . .
H6B H 0.763649 0.542254 0.712109 0.045 Uiso 1 1 calc R U . . .
H6C H 0.678819 0.675354 0.666528 0.045 Uiso 1 1 calc R U . . .
C7 C 0.62750(15) 0.04152(17) 0.60469(9) 0.0278(3) Uani 1 1 d . . . . .
H7A H 0.607716 -0.064929 0.595419 0.042 Uiso 1 1 calc R U . . .
H7B H 0.575193 0.087456 0.631630 0.042 Uiso 1 1 calc R U . . .
H7C H 0.710677 0.051790 0.638089 0.042 Uiso 1 1 calc R U . . .
H1 H 0.750000 0.750000 0.500000 0.074(13) Uiso 1 2 d S . P . .


_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
Cl2 Cl3 2.3053(8) . ?
Cl2 Cl1 2.2737(8) . ?
O2 C3 1.3431(17) . ?
O2 C7 1.4387(18) . ?
O1 N1 1.3650(16) . ?
O1 H1 1.2087(11) . ?
N1 C1 1.3539(19) . ?
N1 C5 1.3512(19) . ?
C1 H1A 0.9500 . ?
C1 C2 1.364(2) . ?
C5 C4 1.384(2) . ?
C5 C6 1.491(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(2) . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
Cl1 Cl2 Cl3 180.0 . . ?
C3 O2 C7 117.59(12) . . ?
N1 O1 H1 107.59(9) . . ?
C1 N1 O1 118.03(12) . . ?
C5 N1 O1 119.48(13) . . ?
C5 N1 C1 122.39(13) . . ?
N1 C1 H1A 119.7 . . ?
N1 C1 C2 120.61(13) . . ?
C2 C1 H1A 119.7 . . ?
N1 C5 C4 118.55(13) . . ?
N1 C5 C6 117.76(14) . . ?
C4 C5 C6 123.68(14) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.88(13) . . ?
C3 C2 H2 120.6 . . ?
O2 C3 C2 115.68(13) . . ?
O2 C3 C4 125.08(13) . . ?
C4 C3 C2 119.23(13) . . ?
C5 C4 C3 120.30(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 C5 179.99(13) . . . . ?
O1 N1 C1 C2 -175.70(12) . . . . ?
O1 N1 C5 C4 174.53(12) . . . . ?
O1 N1 C5 C6 -5.11(19) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
N1 C5 C4 C3 1.1(2) . . . . ?
C1 N1 C5 C4 -1.8(2) . . . . ?
C1 N1 C5 C6 178.61(13) . . . . ?
C1 C2 C3 O2 178.85(12) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C5 N1 C1 C2 0.6(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C6 C5 C4 C3 -179.30(14) . . . . ?
C7 O2 C3 C2 -172.28(12) . . . . ?
C7 O2 C3 C4 8.4(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_OGH_D49_41
_database_code_depnum_ccdc_archive 'CCDC 2383805'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C9 H14 N O'
_chemical_formula_sum            'C9 H14 Cl N O'
_chemical_formula_weight         187.66
_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 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8661(5)
_cell_length_b                   10.3264(4)
_cell_length_c                   10.6277(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     973.02(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      25.314
_cell_measurement_theta_min      2.751
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.9263.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.253
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12603
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.333
_diffrn_reflns_theta_min         2.750
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1740
_reflns_number_total             1776
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      1.088
_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)+(0.0226P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0528
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5)
1.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.05863(5) 0.68026(4) 0.73670(4) 0.01925(13) Uani 1 1 d . . . . .
O1 O 0.10872(15) 0.61756(15) 0.51566(13) 0.0225(3) Uani 1 1 d . . . . .
H1 H 0.056410 0.637037 0.578788 0.034 Uiso 1 1 calc R U . . .
N1 N 0.23645(18) 0.55323(15) 0.55408(14) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.3656(2) 0.58551(19) 0.49763(18) 0.0182(4) Uani 1 1 d . . . . .
H1A H 0.368071 0.653917 0.437896 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4950(2) 0.51877(19) 0.52683(17) 0.0163(4) Uani 1 1 d . . . . .
H2 H 0.586614 0.540613 0.485617 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3552(2) 0.39121(18) 0.67213(18) 0.0149(4) Uani 1 1 d . . . . .
H4 H 0.349604 0.324918 0.733924 0.018 Uiso 1 1 calc R U . . .
C6 C 0.6358(2) 0.34466(17) 0.65258(17) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.2269(2) 0.45736(18) 0.63973(17) 0.0155(4) Uani 1 1 d . . . . .
H5 H 0.132802 0.435957 0.677055 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4944(2) 0.41923(17) 0.61613(17) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.6035(2) 0.19822(18) 0.64650(19) 0.0204(4) Uani 1 1 d . . . . .
H8A H 0.527131 0.175654 0.709451 0.031 Uiso 1 1 calc R U . . .
H8B H 0.696511 0.150094 0.663724 0.031 Uiso 1 1 calc R U . . .
H8C H 0.566305 0.175739 0.562459 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6787(2) 0.3821(2) 0.78822(17) 0.0185(4) Uani 1 1 d . . . . .
H9A H 0.701445 0.474892 0.791867 0.028 Uiso 1 1 calc R U . . .
H9B H 0.767561 0.332571 0.814434 0.028 Uiso 1 1 calc R U . . .
H9C H 0.594248 0.362674 0.844671 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7691(2) 0.3750(2) 0.56493(18) 0.0194(4) Uani 1 1 d . . . . .
H7A H 0.740768 0.355315 0.477870 0.029 Uiso 1 1 calc R U . . .
H7B H 0.856159 0.322134 0.589084 0.029 Uiso 1 1 calc R U . . .
H7C H 0.795202 0.466934 0.571946 0.029 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 H1 0.8400 . ?
O1 N1 1.375(2) . ?
N1 C1 1.335(3) . ?
N1 C5 1.348(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.374(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C4 C3 1.400(3) . ?
C6 C3 1.522(2) . ?
C6 C8 1.540(3) . ?
C6 C9 1.540(3) . ?
C6 C7 1.536(3) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
N1 O1 H1 109.5 . . ?
C1 N1 O1 116.91(15) . . ?
C1 N1 C5 122.73(17) . . ?
C5 N1 O1 120.26(15) . . ?
N1 C1 H1A 120.3 . . ?
N1 C1 C2 119.31(17) . . ?
C2 C1 H1A 120.3 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.25(17) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 H4 119.3 . . ?
C5 C4 C3 121.44(17) . . ?
C3 C4 H4 119.3 . . ?
C3 C6 C8 109.43(15) . . ?
C3 C6 C9 108.33(15) . . ?
C3 C6 C7 112.08(15) . . ?
C9 C6 C8 109.37(16) . . ?
C7 C6 C8 108.53(15) . . ?
C7 C6 C9 109.07(15) . . ?
N1 C5 C4 118.92(17) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C2 C3 C4 116.33(17) . . ?
C2 C3 C6 122.77(16) . . ?
C4 C3 C6 120.89(16) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 -176.02(17) . . . . ?
O1 N1 C5 C4 177.19(16) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C6 -178.94(17) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C5 C4 C3 C6 -179.74(17) . . . . ?
C3 C4 C5 N1 -1.5(3) . . . . ?
C8 C6 C3 C2 -130.35(18) . . . . ?
C8 C6 C3 C4 50.0(2) . . . . ?
C9 C6 C3 C2 110.48(19) . . . . ?
C9 C6 C3 C4 -69.1(2) . . . . ?
C7 C6 C3 C2 -9.9(2) . . . . ?
C7 C6 C3 C4 170.49(16) . . . . ?

_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_OGH_D49_35
_database_code_depnum_ccdc_archive 'CCDC 2383802'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl3, 2(C7 H9 N O), C14 H19 N2 O2'
_chemical_formula_sum            'C28 H37 Cl3 N4 O4'
_chemical_formula_weight         599.96
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3618(17)
_cell_length_b                   8.291(2)
_cell_length_c                   13.265(3)
_cell_angle_alpha                85.903(9)
_cell_angle_beta                 88.725(7)
_cell_angle_gamma                66.463(8)
_cell_volume                     740.4(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.298
_cell_measurement_theta_min      2.686
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.745372
_exptl_absorpt_correction_T_min  0.621617
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0959 before and 0.0784 after correction.
 The Ratio of minimum to maximum transmission is 0.83.

Final HKLF 4 output contains 28271 reflections, Rint = 0.1199
 (7415 with I > 3sig(I), Rint = 0.0687)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.053
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1199
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.457
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1994
_reflns_number_total             3040
_reflns_special_details          
;
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.059
_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)+(0.0550P)²+0.9600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1578
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9043
 0.0957
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9), C4(H4), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.500000 1.000000 1.000000 0.0328(3) Uani 1 2 d S . P . .
Cl1 Cl 0.77642(15) 0.74680(14) 1.03251(8) 0.0422(3) Uani 1 1 d . . . . .
O1 O 0.6714(4) 0.3999(3) 0.62852(17) 0.0290(6) Uani 1 1 d . . . . .
O2 O -0.1066(4) 0.9558(4) 0.55602(17) 0.0321(6) Uani 1 1 d . . . . .
N1 N 0.6210(4) 0.5660(4) 0.6479(2) 0.0229(6) Uani 1 1 d . . . . .
N2 N -0.0142(4) 0.8943(4) 0.6472(2) 0.0245(6) Uani 1 1 d . . . . .
C2 C 0.6243(5) 0.7811(5) 0.7552(2) 0.0244(7) Uani 1 1 d . . . . .
H2A H 0.665438 0.808374 0.816779 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5105(5) 0.6974(5) 0.5792(3) 0.0263(8) Uani 1 1 d . . . . .
H5 H 0.471804 0.668193 0.517579 0.032 Uiso 1 1 calc R U . . .
C8 C 0.0818(5) 0.7179(5) 0.6670(2) 0.0246(7) Uani 1 1 d . . . . .
C10 C 0.1640(5) 0.7750(5) 0.8325(2) 0.0263(8) Uani 1 1 d . . . . .
C3 C 0.5112(5) 0.9188(5) 0.6872(3) 0.0255(8) Uani 1 1 d . . . . .
C1 C 0.6787(5) 0.6069(5) 0.7364(2) 0.0242(7) Uani 1 1 d . . . . .
C9 C 0.1696(5) 0.6598(5) 0.7607(2) 0.0252(7) Uani 1 1 d . . . . .
H9 H 0.236242 0.536576 0.776561 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4550(5) 0.8697(5) 0.5980(3) 0.0286(8) Uani 1 1 d . . . . .
H4 H 0.376233 0.958846 0.549548 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0260(5) 1.0126(5) 0.7142(2) 0.0261(8) Uani 1 1 d . . . . .
H12 H -0.095159 1.135142 0.697078 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0626(5) 0.9548(5) 0.8077(3) 0.0281(8) Uani 1 1 d . . . . .
H11 H 0.054566 1.037678 0.855288 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2640(6) 0.7089(5) 0.9336(3) 0.0337(9) Uani 1 1 d . . . . .
H14A H 0.393907 0.715831 0.932192 0.051 Uiso 1 1 calc R U . . .
H14B H 0.281265 0.586156 0.948455 0.051 Uiso 1 1 calc R U . . .
H14C H 0.182261 0.781641 0.985952 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0805(6) 0.6017(5) 0.5873(3) 0.0337(9) Uani 1 1 d . . . . .
H13A H 0.147008 0.626287 0.526937 0.051 Uiso 1 1 calc R U . . .
H13B H -0.056617 0.623876 0.570213 0.051 Uiso 1 1 calc R U . . .
H13C H 0.150407 0.478102 0.611970 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7997(6) 0.4559(5) 0.8068(3) 0.0306(8) Uani 1 1 d . . . . .
H6A H 0.727085 0.380961 0.823398 0.046 Uiso 1 1 calc R U . . .
H6B H 0.826254 0.500457 0.868872 0.046 Uiso 1 1 calc R U . . .
H6C H 0.925306 0.386865 0.774617 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4503(6) 1.1079(5) 0.7079(3) 0.0362(9) Uani 1 1 d . . . . .
H7A H 0.473719 1.116301 0.779401 0.054 Uiso 1 1 calc R U . . .
H7B H 0.309200 1.172805 0.692037 0.054 Uiso 1 1 calc R U . . .
H7C H 0.528124 1.158587 0.665872 0.054 Uiso 1 1 calc R U . . .
H2 H 0.000000 1.000000 0.500000 0.08(2) Uiso 1 2 d S . P . .


_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
Cl2 Cl1 2.2873(11) 2_677 ?
Cl2 Cl1 2.2873(11) . ?
O1 N1 1.318(4) . ?
O2 N2 1.363(3) . ?
O2 H2 1.211(2) . ?
N1 C5 1.365(4) . ?
N1 C1 1.366(4) . ?
N2 C8 1.355(4) . ?
N2 C12 1.346(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.392(5) . ?
C2 C1 1.376(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.360(5) . ?
C8 C9 1.376(5) . ?
C8 C13 1.484(5) . ?
C10 C9 1.385(5) . ?
C10 C11 1.393(5) . ?
C10 C14 1.502(5) . ?
C3 C4 1.400(5) . ?
C3 C7 1.493(5) . ?
C1 C6 1.488(5) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.376(5) . ?
C11 H11 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
Cl1 Cl2 Cl1 180.00(6) 2_677 . ?
N2 O2 H2 109.2(2) . . ?
O1 N1 C5 119.7(3) . . ?
O1 N1 C1 120.3(3) . . ?
C5 N1 C1 119.9(3) . . ?
C8 N2 O2 118.8(3) . . ?
C12 N2 O2 118.1(3) . . ?
C12 N2 C8 123.1(3) . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 H2A 118.8 . . ?
C1 C2 C3 122.3(3) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 N1 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
N2 C8 C9 117.4(3) . . ?
N2 C8 C13 117.7(3) . . ?
C9 C8 C13 124.9(3) . . ?
C9 C10 C11 117.6(3) . . ?
C9 C10 C14 121.3(3) . . ?
C11 C10 C14 121.0(3) . . ?
C2 C3 C4 116.0(3) . . ?
C2 C3 C7 122.4(3) . . ?
C4 C3 C7 121.6(3) . . ?
N1 C1 C2 119.4(3) . . ?
N1 C1 C6 116.5(3) . . ?
C2 C1 C6 124.1(3) . . ?
C8 C9 C10 122.2(3) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N2 C12 H12 120.2 . . ?
N2 C12 C11 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C5 C4 179.3(3) . . . . ?
O1 N1 C1 C2 -179.9(3) . . . . ?
O1 N1 C1 C6 0.4(5) . . . . ?
O2 N2 C8 C9 -178.5(3) . . . . ?
O2 N2 C8 C13 0.1(4) . . . . ?
O2 N2 C12 C11 178.8(3) . . . . ?
N1 C5 C4 C3 1.0(5) . . . . ?
N2 C8 C9 C10 -0.8(5) . . . . ?
N2 C12 C11 C10 0.1(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C5 N1 C1 C2 0.0(5) . . . . ?
C5 N1 C1 C6 -179.7(3) . . . . ?
C8 N2 C12 C11 0.1(5) . . . . ?
C3 C2 C1 N1 0.2(5) . . . . ?
C3 C2 C1 C6 179.9(3) . . . . ?
C1 N1 C5 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C7 179.4(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C12 N2 C8 C9 0.3(5) . . . . ?
C12 N2 C8 C13 178.9(3) . . . . ?
C11 C10 C9 C8 1.0(5) . . . . ?
C14 C10 C9 C8 -178.8(3) . . . . ?
C14 C10 C11 C12 179.2(3) . . . . ?
C13 C8 C9 C10 -179.3(3) . . . . ?
C7 C3 C4 C5 -180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9043
2 0.0957

####################################################################### 
# 
# 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_OGH_D49_33
_database_code_depnum_ccdc_archive 'CCDC 2383806'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C7 H10 N O2'
_chemical_formula_sum            'C7 H10 Cl N O2'
_chemical_formula_weight         175.61
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7469(4)
_cell_length_b                   9.1814(5)
_cell_length_c                   13.0548(7)
_cell_angle_alpha                82.272(2)
_cell_angle_beta                 80.701(2)
_cell_angle_gamma                66.100(2)
_cell_volume                     835.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.170
_cell_measurement_theta_min      2.897
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0945 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.9189.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.192
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34530
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.433
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2926
_reflns_number_total             3416
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.046
_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)+(0.0205P)²+0.5244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0665
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12)
1.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C7(H7A,H7B,H7C)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.41196(5) 0.18903(4) 0.54750(3) 0.02031(9) Uani 1 1 d . . . . .
Cl2 Cl -0.29558(5) 0.67177(4) 0.09376(3) 0.02199(10) Uani 1 1 d . . . . .
O4 O 0.02112(15) -0.08192(12) 0.27025(8) 0.0214(2) Uani 1 1 d . . . . .
O1 O -0.67926(14) 0.26655(14) 0.39823(8) 0.0241(2) Uani 1 1 d . . . . .
H1 H -0.612396 0.243957 0.447269 0.036 Uiso 1 1 calc R U . . .
O2 O -0.24039(15) 0.14685(12) 0.02510(8) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.02147(16) 0.51524(13) 0.21283(9) 0.0261(2) Uani 1 1 d . . . . .
H3 H -0.067801 0.575499 0.178749 0.039 Uiso 1 1 calc R U . . .
N1 N -0.56258(17) 0.23939(15) 0.30451(9) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.01735(17) 0.36478(15) 0.23024(9) 0.0194(3) Uani 1 1 d . . . . .
C9 C -0.06430(19) 0.17271(17) 0.33942(11) 0.0167(3) Uani 1 1 d . . . . .
H9 H -0.120480 0.140701 0.403865 0.020 Uiso 1 1 calc R U . . .
C2 C -0.4135(2) 0.33359(17) 0.15597(11) 0.0165(3) Uani 1 1 d . . . . .
H2 H -0.383145 0.416806 0.116809 0.020 Uiso 1 1 calc R U . . .
C10 C 0.0191(2) 0.06561(17) 0.26219(11) 0.0179(3) Uani 1 1 d . . . . .
C1 C -0.52168(19) 0.36104(17) 0.25203(11) 0.0173(3) Uani 1 1 d . . . . .
C4 C -0.3947(2) 0.06240(17) 0.17451(12) 0.0198(3) Uani 1 1 d . . . . .
H4 H -0.351505 -0.040011 0.148778 0.024 Uiso 1 1 calc R U . . .
C3 C -0.34883(19) 0.18451(17) 0.11621(11) 0.0170(3) Uani 1 1 d . . . . .
C8 C -0.06596(19) 0.32530(17) 0.32297(11) 0.0172(3) Uani 1 1 d . . . . .
C5 C -0.5024(2) 0.09322(17) 0.26876(11) 0.0198(3) Uani 1 1 d . . . . .
H5 H -0.535088 0.012046 0.309235 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0594(2) -0.13750(18) 0.36751(12) 0.0232(3) Uani 1 1 d . . . . .
H14A H -0.060050 -0.242216 0.360516 0.035 Uiso 1 1 calc R U . . .
H14B H -0.189933 -0.061272 0.385212 0.035 Uiso 1 1 calc R U . . .
H14C H 0.017209 -0.146697 0.422734 0.035 Uiso 1 1 calc R U . . .
C6 C -0.5934(2) 0.51544(18) 0.30059(12) 0.0223(3) Uani 1 1 d . . . . .
H6A H -0.732700 0.562668 0.307044 0.033 Uiso 1 1 calc R U . . .
H6B H -0.543596 0.588549 0.256939 0.033 Uiso 1 1 calc R U . . .
H6C H -0.551337 0.496895 0.369789 0.033 Uiso 1 1 calc R U . . .
C13 C -0.1524(2) 0.44617(17) 0.40131(12) 0.0215(3) Uani 1 1 d . . . . .
H13A H -0.052578 0.469711 0.424117 0.032 Uiso 1 1 calc R U . . .
H13B H -0.217016 0.404289 0.461316 0.032 Uiso 1 1 calc R U . . .
H13C H -0.244584 0.544231 0.370165 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1044(2) 0.11342(19) 0.16799(11) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.163242 0.041723 0.114711 0.026 Uiso 1 1 calc R U . . .
C12 C 0.1017(2) 0.26373(19) 0.15400(11) 0.0227(3) Uani 1 1 d . . . . .
H12 H 0.159057 0.297672 0.090659 0.027 Uiso 1 1 calc R U . . .
C7 C -0.2032(2) 0.27333(18) -0.04083(11) 0.0233(3) Uani 1 1 d . . . . .
H7A H -0.124349 0.230437 -0.105083 0.035 Uiso 1 1 calc R U . . .
H7B H -0.136342 0.317101 -0.004134 0.035 Uiso 1 1 calc R U . . .
H7C H -0.323891 0.358112 -0.057918 0.035 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
O4 C10 1.3384(17) . ?
O4 C14 1.4455(18) . ?
O1 H1 0.8400 . ?
O1 N1 1.3850(15) . ?
O2 C3 1.3388(17) . ?
O2 C7 1.4471(17) . ?
O3 H3 0.8400 . ?
O3 N2 1.3820(15) . ?
N1 C1 1.3521(18) . ?
N1 C5 1.3519(19) . ?
N2 C8 1.3537(18) . ?
N2 C12 1.3511(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C9 C8 1.384(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.383(2) . ?
C2 C3 1.395(2) . ?
C10 C11 1.403(2) . ?
C1 C6 1.486(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.403(2) . ?
C4 C5 1.364(2) . ?
C8 C13 1.486(2) . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.359(2) . ?
C12 H12 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C10 O4 C14 118.00(11) . . ?
N1 O1 H1 109.5 . . ?
C3 O2 C7 117.71(11) . . ?
N2 O3 H3 109.5 . . ?
C1 N1 O1 118.72(12) . . ?
C5 N1 O1 117.50(12) . . ?
C5 N1 C1 123.72(12) . . ?
C8 N2 O3 118.63(12) . . ?
C12 N2 O3 117.66(12) . . ?
C12 N2 C8 123.69(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.53(13) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.43(13) . . ?
C3 C2 H2 119.8 . . ?
O4 C10 C9 124.39(13) . . ?
O4 C10 C11 116.40(13) . . ?
C9 C10 C11 119.20(13) . . ?
N1 C1 C2 117.65(13) . . ?
N1 C1 C6 118.59(13) . . ?
C2 C1 C6 123.76(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.87(13) . . ?
O2 C3 C2 124.29(13) . . ?
O2 C3 C4 116.30(13) . . ?
C2 C3 C4 119.39(13) . . ?
N2 C8 C9 117.52(13) . . ?
N2 C8 C13 118.81(13) . . ?
C9 C8 C13 123.67(13) . . ?
N1 C5 C4 119.93(13) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.11(14) . . ?
C12 C11 H11 120.4 . . ?
N2 C12 C11 119.95(14) . . ?
N2 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C10 C11 C12 178.03(13) . . . . ?
O1 N1 C1 C2 -176.52(12) . . . . ?
O1 N1 C1 C6 3.94(18) . . . . ?
O1 N1 C5 C4 176.88(12) . . . . ?
O3 N2 C8 C9 -178.52(12) . . . . ?
O3 N2 C8 C13 1.08(19) . . . . ?
O3 N2 C12 C11 178.88(13) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C9 C8 N2 -0.6(2) . . . . ?
C10 C9 C8 C13 179.85(13) . . . . ?
C10 C11 C12 N2 -0.1(2) . . . . ?
C1 N1 C5 C4 -0.3(2) . . . . ?
C1 C2 C3 O2 -178.55(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C3 C2 C1 N1 -0.5(2) . . . . ?
C3 C2 C1 C6 179.00(13) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
C8 N2 C12 C11 0.6(2) . . . . ?
C8 C9 C10 O4 -177.58(13) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C5 N1 C1 C2 0.6(2) . . . . ?
C5 N1 C1 C6 -178.92(13) . . . . ?
C5 C4 C3 O2 178.99(13) . . . . ?
C5 C4 C3 C2 0.2(2) . . . . ?
C14 O4 C10 C9 -3.5(2) . . . . ?
C14 O4 C10 C11 177.85(12) . . . . ?
C12 N2 C8 C9 -0.3(2) . . . . ?
C12 N2 C8 C13 179.33(13) . . . . ?
C7 O2 C3 C2 -6.2(2) . . . . ?
C7 O2 C3 C4 175.09(12) . . . . ?

_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_OGH_D49_27
_database_code_depnum_ccdc_archive 'CCDC 2383803'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl3, C11 H10 N O, C11 H9 N O'
_chemical_formula_sum            'C22 H19 Cl3 N2 O2'
_chemical_formula_weight         449.74
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.027(3)
_cell_length_b                   11.706(6)
_cell_length_c                   15.295(9)
_cell_angle_alpha                71.538(19)
_cell_angle_beta                 81.375(19)
_cell_angle_gamma                89.527(14)
_cell_volume                     1011.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    506
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      22.591
_cell_measurement_theta_min      3.498
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.745210
_exptl_absorpt_correction_T_min  0.522247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1189 before and 0.0843 after correction.
 The Ratio of minimum to maximum transmission is 0.70.

Final HKLF 4 output contains 17493 reflections, Rint = 0.2284
 (2031 with I > 3sig(I), Rint = 0.1017)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2284
_diffrn_reflns_av_unetI/netI     0.3770
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3636
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.393
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1278
_reflns_number_total             3636
_reflns_special_details          
;
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.3614
_refine_ls_R_factor_gt           0.1321
_refine_ls_restrained_S_all      1.069
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2983
_refine_ls_wR_factor_ref         0.4380
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.77152
 0.22848
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C22) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C20) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C18) \\sim Ueq, : with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C7(H7), C22(H22), C4(H4), C11(H11), C21(H21), C9(H9),
 C8(H8), C1(H1A), C15(H15), C12(H12), C13(H13), C14(H14), C20(H20), C10(H10),
 C3(H3), C2(H2)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.8467(6) 0.0770(3) 0.7315(3) 0.0382(10) Uani 1 1 d . . . . .
Cl3 Cl 0.9033(7) 0.1396(4) 0.5685(3) 0.0432(12) Uani 1 1 d . . . . .
Cl1 Cl 0.7892(7) 0.0160(3) 0.8900(3) 0.0427(11) Uani 1 1 d . . . . .
O1 O 1.0047(16) 0.3263(10) 0.3103(7) 0.039(3) Uani 1 1 d . U . . .
H1 H 0.987926 0.390577 0.267942 0.058 Uiso 1 1 calc R U . . .
O2 O 1.0525(16) 0.5224(9) 0.1885(7) 0.037(3) Uani 1 1 d . U . . .
N2 N 0.885(2) 0.5907(12) 0.1544(9) 0.036(3) Uani 1 1 d . U . . .
N1 N 0.805(2) 0.2634(11) 0.3425(8) 0.033(3) Uani 1 1 d . U . . .
C19 C 0.878(3) 0.2504(14) 0.0903(10) 0.035(4) Uani 1 1 d . U . . .
H19 H 1.003033 0.213678 0.066210 0.042 Uiso 1 1 calc R U . . .
C18 C 0.905(2) 0.3665(14) 0.0913(10) 0.033(4) Uani 1 1 d . U . . .
H18 H 1.047851 0.408178 0.071038 0.040 Uiso 1 1 calc R U . . .
C7 C 0.449(2) 0.5121(14) 0.3440(10) 0.032(4) Uani 1 1 d . U . . .
H7 H 0.329163 0.478321 0.324900 0.038 Uiso 1 1 calc R U . . .
C16 C 0.717(2) 0.5522(13) 0.1195(10) 0.030(3) Uani 1 1 d . U . . .
C17 C 0.715(2) 0.4218(13) 0.1235(10) 0.028(3) Uani 1 1 d . U . . .
C22 C 0.504(2) 0.3592(14) 0.1520(10) 0.030(4) Uani 1 1 d . U . . .
H22 H 0.373924 0.396877 0.171155 0.037 Uiso 1 1 calc R U . . .
C4 C 0.424(2) 0.2414(14) 0.4080(11) 0.036(4) Uani 1 1 d . U . . .
H4 H 0.290613 0.274072 0.430281 0.043 Uiso 1 1 calc R U . . .
C11 C 0.796(2) 0.4894(14) 0.4058(10) 0.030(4) Uani 1 1 d . U . . .
H11 H 0.916712 0.441515 0.428022 0.036 Uiso 1 1 calc R U . . .
C21 C 0.491(3) 0.2413(14) 0.1512(11) 0.036(4) Uani 1 1 d . U . . .
H21 H 0.350420 0.197944 0.170859 0.043 Uiso 1 1 calc R U . . .
C9 C 0.608(3) 0.6765(15) 0.3747(11) 0.041(4) Uani 1 1 d . U . . .
H9 H 0.601126 0.756952 0.376382 0.049 Uiso 1 1 calc R U . . .
C6 C 0.623(3) 0.4415(14) 0.3725(10) 0.036(4) Uani 1 1 d . U . . .
C8 C 0.441(2) 0.6307(14) 0.3422(10) 0.034(4) Uani 1 1 d . U . . .
H8 H 0.322487 0.679445 0.318827 0.041 Uiso 1 1 calc R U . . .
C1 C 0.805(3) 0.1456(16) 0.3434(11) 0.043(4) Uani 1 1 d . U . . .
H1A H 0.939915 0.112745 0.322613 0.052 Uiso 1 1 calc R U . . .
C15 C 0.560(3) 0.6293(14) 0.0843(10) 0.035(4) Uani 1 1 d . U . . .
H15 H 0.442958 0.602803 0.059044 0.042 Uiso 1 1 calc R U . . .
C5 C 0.620(3) 0.3149(14) 0.3751(10) 0.033(4) Uani 1 1 d . U . . .
C12 C 0.907(3) 0.7082(15) 0.1544(11) 0.036(4) Uani 1 1 d . U . . .
H12 H 1.029392 0.734296 0.176745 0.043 Uiso 1 1 calc R U . . .
C13 C 0.741(2) 0.7876(15) 0.1203(10) 0.036(4) Uani 1 1 d . U . . .
H13 H 0.747404 0.868252 0.121285 0.043 Uiso 1 1 calc R U . . .
C14 C 0.570(3) 0.7483(15) 0.0853(11) 0.042(4) Uani 1 1 d . U . . .
H14 H 0.458423 0.802118 0.061639 0.050 Uiso 1 1 calc R U . . .
C20 C 0.677(3) 0.1853(16) 0.1227(11) 0.046(4) Uani 1 1 d . U . . .
H20 H 0.666326 0.103334 0.125350 0.056 Uiso 1 1 calc R U . . .
C10 C 0.785(2) 0.6081(15) 0.4051(10) 0.035(4) Uani 1 1 d . U . . .
H10 H 0.900278 0.642655 0.425788 0.042 Uiso 1 1 calc R U . . .
C3 C 0.418(3) 0.1231(15) 0.4095(11) 0.041(4) Uani 1 1 d . U . . .
H3 H 0.283283 0.074346 0.434201 0.050 Uiso 1 1 calc R U . . .
C2 C 0.611(3) 0.0763(15) 0.3742(10) 0.040(4) Uani 1 1 d . U . . .
H2 H 0.607122 -0.003644 0.371656 0.048 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
Cl2 Cl3 2.337(6) . ?
Cl2 Cl1 2.272(6) . ?
O1 H1 0.8400 . ?
O1 N1 1.359(14) . ?
O2 N2 1.343(14) . ?
N2 C16 1.359(17) . ?
N2 C12 1.382(19) . ?
N1 C1 1.375(19) . ?
N1 C5 1.367(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.38(2) . ?
C19 C20 1.37(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.413(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.368(19) . ?
C7 C8 1.38(2) . ?
C16 C17 1.507(19) . ?
C16 C15 1.353(19) . ?
C17 C22 1.412(18) . ?
C22 H22 0.9500 . ?
C22 C21 1.39(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(19) . ?
C4 C3 1.38(2) . ?
C11 H11 0.9500 . ?
C11 C6 1.418(19) . ?
C11 C10 1.39(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.38(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.369(19) . ?
C9 C10 1.38(2) . ?
C6 C5 1.47(2) . ?
C8 H8 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2 1.37(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.40(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.40(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(19) . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.39(2) . ?
C2 H2 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
Cl1 Cl2 Cl3 179.6(2) . . ?
N1 O1 H1 109.5 . . ?
O2 N2 C16 124.7(13) . . ?
O2 N2 C12 112.9(13) . . ?
C16 N2 C12 122.3(13) . . ?
O1 N1 C1 115.7(12) . . ?
O1 N1 C5 120.8(13) . . ?
C5 N1 C1 123.4(14) . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C20 C19 C18 122.8(15) . . ?
C19 C18 H18 121.1 . . ?
C19 C18 C17 117.9(15) . . ?
C17 C18 H18 121.1 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.2(15) . . ?
C8 C7 H7 118.9 . . ?
N2 C16 C17 116.6(12) . . ?
C15 C16 N2 120.0(14) . . ?
C15 C16 C17 123.3(14) . . ?
C18 C17 C16 123.3(14) . . ?
C22 C17 C18 120.2(13) . . ?
C22 C17 C16 116.1(13) . . ?
C17 C22 H22 120.8 . . ?
C21 C22 C17 118.3(14) . . ?
C21 C22 H22 120.8 . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.3(15) . . ?
C6 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C6 118.0(14) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 C22 121.9(16) . . ?
C20 C21 H21 119.1 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(16) . . ?
C10 C9 H9 119.4 . . ?
C7 C6 C11 119.2(15) . . ?
C7 C6 C5 119.7(15) . . ?
C11 C6 C5 121.0(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(14) . . ?
C9 C8 H8 120.8 . . ?
N1 C1 H1A 120.3 . . ?
C2 C1 N1 119.4(15) . . ?
C2 C1 H1A 120.3 . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.8(15) . . ?
C14 C15 H15 120.1 . . ?
N1 C5 C4 116.0(14) . . ?
N1 C5 C6 122.2(15) . . ?
C4 C5 C6 121.7(14) . . ?
N2 C12 H12 121.1 . . ?
N2 C12 C13 117.8(14) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.7(15) . . ?
C14 C13 H13 120.2 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.3(15) . . ?
C13 C14 H14 119.9 . . ?
C19 C20 C21 118.7(16) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.9(15) . . ?
C9 C10 H10 119.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 118.9(16) . . ?
C2 C3 H3 120.5 . . ?
C1 C2 C3 119.8(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 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 -179.7(13) . . . . ?
O1 N1 C5 C4 -178.9(12) . . . . ?
O1 N1 C5 C6 3(2) . . . . ?
O2 N2 C16 C17 3(2) . . . . ?
O2 N2 C16 C15 -178.1(12) . . . . ?
O2 N2 C12 C13 -180.0(13) . . . . ?
N2 C16 C17 C18 -50.2(19) . . . . ?
N2 C16 C17 C22 136.8(14) . . . . ?
N2 C16 C15 C14 -1(2) . . . . ?
N2 C12 C13 C14 -2(2) . . . . ?
N1 C1 C2 C3 -4(2) . . . . ?
C19 C18 C17 C16 -173.8(12) . . . . ?
C19 C18 C17 C22 -1(2) . . . . ?
C18 C19 C20 C21 5(2) . . . . ?
C18 C17 C22 C21 3(2) . . . . ?
C7 C6 C5 N1 136.0(16) . . . . ?
C7 C6 C5 C4 -42(2) . . . . ?
C16 N2 C12 C13 3(2) . . . . ?
C16 C17 C22 C21 176.0(12) . . . . ?
C16 C15 C14 C13 1(2) . . . . ?
C17 C16 C15 C14 178.4(14) . . . . ?
C17 C22 C21 C20 -1(2) . . . . ?
C22 C21 C20 C19 -3(2) . . . . ?
C4 C3 C2 C1 3(2) . . . . ?
C11 C6 C5 N1 -49(2) . . . . ?
C11 C6 C5 C4 133.4(16) . . . . ?
C6 C7 C8 C9 -4(2) . . . . ?
C6 C11 C10 C9 1(2) . . . . ?
C8 C7 C6 C11 3(2) . . . . ?
C8 C7 C6 C5 178.6(14) . . . . ?
C8 C9 C10 C11 -2(2) . . . . ?
C1 N1 C5 C4 -2(2) . . . . ?
C1 N1 C5 C6 -179.4(13) . . . . ?
C15 C16 C17 C18 130.5(17) . . . . ?
C15 C16 C17 C22 -43(2) . . . . ?
C5 N1 C1 C2 3(2) . . . . ?
C5 C4 C3 C2 -2(2) . . . . ?
C12 N2 C16 C17 179.6(13) . . . . ?
C12 N2 C16 C15 -1(2) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
C20 C19 C18 C17 -3(2) . . . . ?
C10 C11 C6 C7 -2(2) . . . . ?
C10 C11 C6 C5 -177.3(14) . . . . ?
C10 C9 C8 C7 3(2) . . . . ?
C3 C4 C5 N1 1(2) . . . . ?
C3 C4 C5 C6 179.0(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.77152
2 0.22848

####################################################################### 
# 
# 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_OGH_D49_57
_database_code_depnum_ccdc_archive 'CCDC 2383807'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl2, C5 H5 N O'
_chemical_formula_sum            'C5 H5 Cl2 N O'
_chemical_formula_weight         166.00
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   13.8648(10)
_cell_length_b                   13.7600(8)
_cell_length_c                   16.1649(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.221(2)
_cell_angle_gamma                90
_cell_volume                     2789.9(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.280
_cell_measurement_theta_min      2.785
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1824 before and 0.0999 after correction.
The Ratio of minimum to maximum transmission is 0.7377.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.134
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28774
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2165
_reflns_number_total             2555
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      1.276
_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)+(0.1189P)²+27.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2460
_refine_ls_wR_factor_ref         0.2593
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.84856
 0.15144
2. Restrained distances
 O1A-N1A \\sim O1B-N1B
 with sigma of 0.02
 N1A-C5A \\sim N1B-C5B
 with sigma of 0.02
 N1A-C1A \\sim N1B-C1B
 with sigma of 0.02
 C5A-C4A \\sim C5B-C4B
 with sigma of 0.02
 C1A-C2A \\sim C1B-C2B
 with sigma of 0.02
 C4A-C3A \\sim C4B-C3B
 with sigma of 0.02
 C3A-C2A \\sim C3B-C2B
 with sigma of 0.02
 O1A-C5A \\sim O1B-C5B
 with sigma of 0.04
 O1A-C1A \\sim O1B-C1B
 with sigma of 0.04
 N1A-C4A \\sim N1B-C4B
 with sigma of 0.04
 N1A-C2A \\sim N1B-C2B
 with sigma of 0.04
 C5A-C1A \\sim C5B-C1B
 with sigma of 0.04
 C5A-C3A \\sim C5B-C3B
 with sigma of 0.04
 C1A-C3A \\sim C1B-C3B
 with sigma of 0.04
 C4A-C2A \\sim C4B-C2B
 with sigma of 0.04
 O2A-N2A \\sim O2B-N2B
 with sigma of 0.02
 N2A-C6A \\sim N2B-C6B
 with sigma of 0.02
 N2A-C10A \\sim N2B-C10B
 with sigma of 0.02
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C10A-C9A \\sim C10B-C9B
 with sigma of 0.02
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 O2A-C6A \\sim O2B-C6B
 with sigma of 0.04
 O2A-C10A \\sim O2B-C10B
 with sigma of 0.04
 N2A-C9A \\sim N2B-C9B
 with sigma of 0.04
 N2A-C7A \\sim N2B-C7B
 with sigma of 0.04
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
 C10A-C8A \\sim C10B-C8B
 with sigma of 0.04
 C9A-C7A \\sim C9B-C7B
 with sigma of 0.04
 Cl4A-Cl3A \\sim Cl3B-Cl4B
 with sigma of 0.02
3. Restrained planarity
 O1B, N1B, C5B, C1B, C2B, C3B, C4B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) = Uanis(Cl4B) = Uanis(Cl2B) = Uanis(Cl3A) = Uanis(Cl3B) =
Uanis(Cl4A) = Uanis(Cl1B) = Uanis(Cl1A)
Uanis(C1B) = Uanis(C5A) = Uanis(C4A) = Uanis(C5B) = Uanis(C4B) = Uanis(C3A) =
Uanis(C3B) = Uanis(C2A) = Uanis(C2B) = Uanis(C1A)
Uanis(N1A) = Uanis(N1B)
Uanis(O1A) = Uanis(O1B)
Uanis(C10B) = Uanis(C9B) = Uanis(C10A) = Uanis(C8B) = Uanis(C9A) = Uanis(C7B) =
Uanis(C8A) = Uanis(C7A) = Uanis(C6B) = Uanis(C6A)
Uanis(N2B) = Uanis(N2A)
Uanis(O2B) = Uanis(O2A)
5. Others
 Fixed Sof: Cl2A(0.95) Cl3A(0.95) Cl4A(0.95) Cl1A(0.95) O1A(0.95) O2A(0.95)
 N1A(0.95) N2A(0.95) C5A(0.95) H5A(0.95) C6A(0.95) H6A(0.95) C10A(0.95)
 H10A(0.95) C1A(0.95) H1A(0.95) C9A(0.95) H9A(0.95) C7A(0.95) H7A(0.95)
 C4A(0.95) H4A(0.95) C8A(0.95) H8A(0.95) C3A(0.95) H3A(0.95) C2A(0.95)
 H2A(0.95) Cl4B(0.05) Cl3B(0.05) Cl2B(0.05) Cl1B(0.05) O1B(0.05) C3B(0.05)
 H3B(0.05) C4B(0.05) H4B(0.05) C5B(0.05) H5B(0.05) N1B(0.05) C1B(0.05)
 H1B(0.05) C2B(0.05) H2B(0.05) C10B(0.05) H10B(0.05) O2B(0.05) N2B(0.05)
 C6B(0.05) H6B(0.05) C9B(0.05) H9B(0.05) C7B(0.05) H7B(0.05) C8B(0.05) H8B(0.05)
6.a Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C10A(H10A), C1A(H1A), C9A(H9A), C7A(H7A), C4A(H4A),
 C8A(H8A), C3A(H3A), C2A(H2A), C3B(H3B), C4B(H4B), C5B(H5B), C1B(H1B), C2B(H2B),
  C10B(H10B), C6B(H6B), C9B(H9B), C7B(H7B), C8B(H8B)
6.b Fitted hexagon refined as free rotating group:
 C3B(C4B,C5B,N1B,C1B,C2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2A Cl 0.38805(15) 1.04845(13) 0.79125(13) 0.0202(4) Uani 0.95 1 d . . P A 1
Cl3A Cl 0.38522(14) 0.68924(13) 0.78519(12) 0.0202(4) Uani 0.95 1 d D . P B 1
Cl4A Cl 0.42370(15) 0.54674(13) 0.81995(12) 0.0202(4) Uani 0.95 1 d D . P B 1
Cl1A Cl 0.42781(14) 1.19072(13) 0.82599(12) 0.0202(4) Uani 0.95 1 d . . P A 1
O1A O 1.0128(4) 1.1324(3) 1.1299(4) 0.0217(12) Uani 0.95 1 d D . P C 1
O2A O 0.6542(4) 0.8676(3) 0.7644(3) 0.0225(12) Uani 0.95 1 d D . P D 1
N1A N 0.9070(5) 1.1301(4) 1.0917(4) 0.0167(13) Uani 0.95 1 d D . P C 1
N2A N 0.6794(5) 0.8704(4) 0.8533(4) 0.0162(13) Uani 0.95 1 d D . P D 1
C5A C 0.8537(6) 1.1305(5) 1.1451(5) 0.0226(8) Uani 0.95 1 d D . P C 1
H5A H 0.892266 1.133125 1.209738 0.027 Uiso 0.95 1 calc R U P C 1
C6A C 0.6000(7) 0.8715(6) 0.8815(5) 0.0232(9) Uani 0.95 1 d D . P D 1
H6A H 0.527656 0.869920 0.837738 0.028 Uiso 0.95 1 calc R U P D 1
C10A C 0.7831(7) 0.8718(6) 0.9146(5) 0.0232(9) Uani 0.95 1 d D . P D 1
H10A H 0.837917 0.870782 0.894074 0.028 Uiso 0.95 1 calc R U P D 1
C1A C 0.8547(6) 1.1284(5) 0.9994(5) 0.0226(8) Uani 0.95 1 d D . P C 1
H1A H 0.893296 1.129208 0.963000 0.027 Uiso 0.95 1 calc R U P C 1
C9A C 0.8089(7) 0.8749(5) 1.0069(6) 0.0232(9) Uani 0.95 1 d D . P D 1
H9A H 0.881713 0.876203 1.049728 0.028 Uiso 0.95 1 calc R U P D 1
C7A C 0.6244(7) 0.8749(5) 0.9740(5) 0.0232(9) Uani 0.95 1 d D . P D 1
H7A H 0.568948 0.876467 0.993713 0.028 Uiso 0.95 1 calc R U P D 1
C4A C 0.7441(6) 1.1273(5) 1.1064(5) 0.0226(8) Uani 0.95 1 d D . P C 1
H4A H 0.706959 1.126495 1.144072 0.027 Uiso 0.95 1 calc R U P C 1
C8A C 0.7305(7) 0.8760(5) 1.0377(5) 0.0232(9) Uani 0.95 1 d D . P D 1
H8A H 0.748438 0.877562 1.101341 0.028 Uiso 0.95 1 calc R U P D 1
C3A C 0.6878(6) 1.1251(5) 1.0114(5) 0.0226(8) Uani 0.95 1 d D . P C 1
H3A H 0.612092 1.123538 0.983565 0.027 Uiso 0.95 1 calc R U P C 1
C2A C 0.7443(6) 1.1254(5) 0.9584(5) 0.0226(8) Uani 0.95 1 d D . P C 1
H2A H 0.707101 1.123495 0.893642 0.027 Uiso 0.95 1 calc R U P C 1
Cl4B Cl 0.388(3) 0.573(2) 0.788(3) 0.0202(4) Uani 0.05 1 d D . P E 2
Cl3B Cl 0.422(3) 0.718(2) 0.819(2) 0.0202(4) Uani 0.05 1 d D . P E 2
Cl2B Cl 0.430(3) 1.071(3) 0.824(2) 0.0202(4) Uani 0.05 1 d . . P F 2
Cl1B Cl 0.387(3) 1.218(2) 0.788(2) 0.0202(4) Uani 0.05 1 d . . P F 2
O1B O 0.838(7) 1.110(5) 1.229(4) 0.0217(12) Uani 0.05 1 d D . P G 2
C3B C 0.790(9) 1.126(6) 0.961(4) 0.0226(8) Uani 0.05 1 d DG . P G 2
H3B H 0.779300 1.129833 0.898910 0.027 Uiso 0.05 1 calc R U P G 2
C4B C 0.703(7) 1.130(7) 0.982(4) 0.0226(8) Uani 0.05 1 d DG . P G 2
H4B H 0.633131 1.136811 0.935241 0.027 Uiso 0.05 1 calc R U P G 2
C5B C 0.719(5) 1.125(6) 1.073(5) 0.0226(8) Uani 0.05 1 d DG . P G 2
H5B H 0.659472 1.127525 1.087957 0.027 Uiso 0.05 1 calc R U P G 2
N1B N 0.821(5) 1.115(4) 1.142(4) 0.0167(13) Uani 0.05 1 d DG . P G 2
C1B C 0.908(5) 1.111(6) 1.121(5) 0.0226(8) Uani 0.05 1 d DG . P G 2
H1B H 0.978154 1.104284 1.168015 0.027 Uiso 0.05 1 calc R U P G 2
C2B C 0.892(8) 1.116(7) 1.030(6) 0.0226(8) Uani 0.05 1 d DG . P G 2
H2B H 0.951814 1.113570 1.015298 0.027 Uiso 0.05 1 calc R U P G 2
C10B C 0.650(6) 0.896(12) 0.851(5) 0.0232(9) Uani 0.05 1 d D . P H 2
H10B H 0.610236 0.912342 0.788000 0.028 Uiso 0.05 1 calc R U P H 2
O2B O 0.495(5) 0.895(6) 0.872(6) 0.0225(12) Uani 0.05 1 d D . P H 2
N2B N 0.601(5) 0.885(8) 0.907(4) 0.0162(13) Uani 0.05 1 d D . P H 2
C6B C 0.659(6) 0.887(11) 0.999(4) 0.0232(9) Uani 0.05 1 d D . P H 2
H6B H 0.623790 0.889421 1.038205 0.028 Uiso 0.05 1 calc R U P H 2
C9B C 0.759(6) 0.883(11) 0.885(7) 0.0232(9) Uani 0.05 1 d D . P H 2
H9B H 0.792221 0.879656 0.844431 0.028 Uiso 0.05 1 calc R U P H 2
C7B C 0.769(6) 0.884(10) 1.036(5) 0.0232(9) Uani 0.05 1 d D . P H 2
H7B H 0.810215 0.888224 1.099947 0.028 Uiso 0.05 1 calc R U P H 2
C8B C 0.820(5) 0.876(10) 0.978(7) 0.0232(9) Uani 0.05 1 d D . P H 2
H8B H 0.894590 0.865608 1.001969 0.028 Uiso 0.05 1 calc R U P H 2


_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
Cl2A Cl1A 2.046(3) . ?
Cl3A Cl4A 2.047(3) . ?
O1A N1A 1.328(8) . ?
O2A N2A 1.327(8) . ?
N1A C5A 1.355(9) . ?
N1A C1A 1.353(9) . ?
N2A C6A 1.359(11) . ?
N2A C10A 1.355(11) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.376(10) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.386(11) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.378(12) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.385(10) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.376(12) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.390(11) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.395(9) . ?
C8A H8A 0.9500 . ?
C3A H3A 0.9500 . ?
C3A C2A 1.385(10) . ?
C2A H2A 0.9500 . ?
Cl4B Cl3B 2.059(19) . ?
Cl2B Cl1B 2.12(5) . ?
O1B N1B 1.320(19) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.3900(10) . ?
C3B C2B 1.3900(15) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.3900 . ?
C5B H5B 0.9500 . ?
C5B N1B 1.3900 . ?
N1B C1B 1.3900(11) . ?
C1B H1B 0.9500 . ?
C1B C2B 1.3900 . ?
C2B H2B 0.9500 . ?
C10B H10B 0.9500 . ?
C10B N2B 1.36(2) . ?
C10B C9B 1.38(2) . ?
O2B N2B 1.33(2) . ?
N2B C6B 1.36(2) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.39(2) . ?
C9B H9B 0.9500 . ?
C9B C8B 1.38(2) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.39(2) . ?
C8B H8B 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
O1A N1A C5A 119.9(6) . . ?
O1A N1A C1A 118.7(6) . . ?
C1A N1A C5A 121.4(6) . . ?
O2A N2A C6A 119.1(6) . . ?
O2A N2A C10A 120.0(7) . . ?
C10A N2A C6A 120.9(7) . . ?
N1A C5A H5A 119.8 . . ?
N1A C5A C4A 120.5(7) . . ?
C4A C5A H5A 119.8 . . ?
N2A C6A H6A 119.9 . . ?
N2A C6A C7A 120.1(7) . . ?
C7A C6A H6A 119.9 . . ?
N2A C10A H10A 120.1 . . ?
N2A C10A C9A 119.8(8) . . ?
C9A C10A H10A 120.1 . . ?
N1A C1A H1A 120.2 . . ?
N1A C1A C2A 119.5(7) . . ?
C2A C1A H1A 120.2 . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A C10A 120.8(7) . . ?
C8A C9A H9A 119.6 . . ?
C6A C7A H7A 120.2 . . ?
C6A C7A C8A 119.6(8) . . ?
C8A C7A H7A 120.2 . . ?
C5A C4A H4A 120.3 . . ?
C5A C4A C3A 119.5(7) . . ?
C3A C4A H4A 120.3 . . ?
C9A C8A C7A 118.8(7) . . ?
C9A C8A H8A 120.6 . . ?
C7A C8A H8A 120.6 . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A C4A 118.9(7) . . ?
C2A C3A H3A 120.6 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.3(7) . . ?
C3A C2A H2A 119.9 . . ?
C4B C3B H3B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B C3B 120.00(12) . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B N1B 120.00(7) . . ?
N1B C5B H5B 120.0 . . ?
O1B N1B C5B 121(2) . . ?
O1B N1B C1B 119(2) . . ?
C1B N1B C5B 120.0 . . ?
N1B C1B H1B 120.0 . . ?
C2B C1B N1B 120.00(7) . . ?
C2B C1B H1B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B C3B 120.00(9) . . ?
C1B C2B H2B 120.0 . . ?
N2B C10B H10B 120.2 . . ?
N2B C10B C9B 120(3) . . ?
C9B C10B H10B 120.2 . . ?
C10B N2B C6B 120(3) . . ?
O2B N2B C10B 119(3) . . ?
O2B N2B C6B 119(3) . . ?
N2B C6B H6B 120.1 . . ?
N2B C6B C7B 120(3) . . ?
C7B C6B H6B 120.1 . . ?
C10B C9B H9B 119.8 . . ?
C10B C9B C8B 120(3) . . ?
C8B C9B H9B 119.8 . . ?
C6B C7B H7B 120.1 . . ?
C6B C7B C8B 120(3) . . ?
C8B C7B H7B 120.1 . . ?
C9B C8B C7B 118(3) . . ?
C9B C8B H8B 120.8 . . ?
C7B C8B H8B 120.8 . . ?

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
O1A N1A C5A C4A -179.4(6) . . . . ?
O1A N1A C1A C2A 179.6(6) . . . . ?
O2A N2A C6A C7A -179.7(6) . . . . ?
O2A N2A C10A C9A 179.9(6) . . . . ?
N1A C5A C4A C3A -1.1(11) . . . . ?
N1A C1A C2A C3A 0.6(10) . . . . ?
N2A C6A C7A C8A -0.7(11) . . . . ?
N2A C10A C9A C8A 0.3(11) . . . . ?
C5A N1A C1A C2A -1.1(10) . . . . ?
C5A C4A C3A C2A 0.6(10) . . . . ?
C6A N2A C10A C9A -0.2(10) . . . . ?
C6A C7A C8A C9A 0.8(11) . . . . ?
C10A N2A C6A C7A 0.5(10) . . . . ?
C10A C9A C8A C7A -0.5(12) . . . . ?
C1A N1A C5A C4A 1.3(10) . . . . ?
C4A C3A C2A C1A -0.4(10) . . . . ?
O1B N1B C1B C2B 179.9(10) . . . . ?
C3B C4B C5B N1B 0.0 . . . . ?
C4B C3B C2B C1B 0.0 . . . . ?
C4B C5B N1B O1B -179.9(10) . . . . ?
C4B C5B N1B C1B 0.0 . . . . ?
C5B N1B C1B C2B 0.0 . . . . ?
N1B C1B C2B C3B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C10B N2B C6B C7B -10(19) . . . . ?
C10B C9B C8B C7B -2(21) . . . . ?
O2B N2B C6B C7B -175(12) . . . . ?
N2B C10B C9B C8B -11(23) . . . . ?
N2B C6B C7B C8B -3(20) . . . . ?
C6B C7B C8B C9B 8(20) . . . . ?
C9B C10B N2B O2B -178(13) . . . . ?
C9B C10B N2B C6B 17(20) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.84856
2 0.15144

####################################################################### 
# 
# 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_OGH_D49_42
_database_code_depnum_ccdc_archive 'CCDC 2383804'
loop_
_audit_author_name
_audit_author_address
'Niklas Limberg'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2024-09-11
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl3, C16 H23 N2 O2'
_chemical_formula_sum            'C16 H23 Cl3 N2 O2'
_chemical_formula_weight         381.71
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2228(13)
_cell_length_b                   8.5908(16)
_cell_length_c                   8.6321(17)
_cell_angle_alpha                68.449(6)
_cell_angle_beta                 65.454(6)
_cell_angle_gamma                78.430(7)
_cell_volume                     452.42(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.299
_cell_measurement_theta_min      2.553
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1192 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.7451.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.177
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14067
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.553
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1497
_reflns_number_total             1840
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.048
_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)+(0.0431P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0954
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4)
1.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.000000 0.000000 1.000000 0.02048(18) Uani 1 2 d S . P . .
Cl2 Cl 0.99660(8) -0.07068(6) 0.76927(7) 0.02547(17) Uani 1 1 d . . . . .
O1 O 0.4206(2) 0.49113(17) 0.90470(16) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.5614(2) 0.49994(19) 0.73686(19) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.7704(3) 0.6598(2) 0.4497(2) 0.0153(4) Uani 1 1 d . . . . .
H2 H 0.823982 0.764401 0.367655 0.018 Uiso 1 1 calc R U . . .
C4 C 0.7502(3) 0.3671(2) 0.5190(2) 0.0152(4) Uani 1 1 d . . . . .
H4 H 0.789081 0.268599 0.484729 0.018 Uiso 1 1 calc R U . . .
C5 C 0.6151(3) 0.3573(2) 0.6917(2) 0.0154(4) Uani 1 1 d . . . . .
C1 C 0.6346(3) 0.6515(2) 0.6216(2) 0.0150(4) Uani 1 1 d . . . . .
C3 C 0.8305(3) 0.5184(2) 0.3943(2) 0.0154(4) Uani 1 1 d . . . . .
C6 C 0.5652(3) 0.7989(2) 0.6882(3) 0.0203(4) Uani 1 1 d . . . . .
H6A H 0.416071 0.812308 0.732713 0.030 Uiso 1 1 calc R U . . .
H6B H 0.622945 0.900129 0.589728 0.030 Uiso 1 1 calc R U . . .
H6C H 0.611106 0.781105 0.785809 0.030 Uiso 1 1 calc R U . . .
C8 C 0.5282(3) 0.1983(2) 0.8316(3) 0.0202(4) Uani 1 1 d . . . . .
H8A H 0.581004 0.168064 0.927337 0.030 Uiso 1 1 calc R U . . .
H8B H 0.567103 0.108625 0.777360 0.030 Uiso 1 1 calc R U . . .
H8C H 0.379227 0.213593 0.882125 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9753(3) 0.5293(3) 0.2060(2) 0.0189(4) Uani 1 1 d . . . . .
H7A H 0.898068 0.555789 0.128343 0.028 Uiso 1 1 calc R U . . .
H7B H 1.052697 0.421643 0.205842 0.028 Uiso 1 1 calc R U . . .
H7C H 1.069621 0.617503 0.161095 0.028 Uiso 1 1 calc R U . . .
H1 H 0.500000 0.500000 1.000000 0.072(14) Uiso 1 2 d S . P . .


_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 Cl2 2.2959(6) 2_757 ?
Cl1 Cl2 2.2959(6) . ?
O1 N1 1.3658(19) . ?
O1 H1 1.2114(13) . ?
N1 C5 1.356(2) . ?
N1 C1 1.361(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.382(3) . ?
C2 C3 1.392(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C4 C3 1.393(3) . ?
C5 C8 1.490(3) . ?
C1 C6 1.492(3) . ?
C3 C7 1.503(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
Cl2 Cl1 Cl2 180.00(2) 2_757 . ?
N1 O1 H1 111.03(12) . . ?
C5 N1 O1 117.87(15) . . ?
C5 N1 C1 123.40(16) . . ?
C1 N1 O1 118.68(15) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.43(17) . . ?
C3 C2 H2 119.3 . . ?
C5 C4 H4 119.3 . . ?
C5 C4 C3 121.40(17) . . ?
C3 C4 H4 119.3 . . ?
N1 C5 C4 118.11(17) . . ?
N1 C5 C8 118.24(16) . . ?
C4 C5 C8 123.64(17) . . ?
N1 C1 C2 118.07(17) . . ?
N1 C1 C6 118.26(16) . . ?
C2 C1 C6 123.67(17) . . ?
C2 C3 C4 117.59(17) . . ?
C2 C3 C7 121.06(17) . . ?
C4 C3 C7 121.34(17) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C5 C4 176.92(15) . . . . ?
O1 N1 C5 C8 -4.0(2) . . . . ?
O1 N1 C1 C2 -177.29(15) . . . . ?
O1 N1 C1 C6 3.2(2) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
C5 N1 C1 C6 -179.38(17) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C5 C4 C3 C7 -179.26(17) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C1 N1 C5 C8 178.49(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C7 178.85(17) . . . . ?
C3 C2 C1 N1 0.4(3) . . . . ?
C3 C2 C1 C6 179.94(17) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
C3 C4 C5 C8 -178.62(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
