# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_TMANO24DCB_200K
_database_code_depnum_ccdc_archive 'CCDC 1545110'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 Cl2 N O3'
_chemical_formula_sum            'C10 H13 Cl2 N O3'
_chemical_formula_weight         266.11
_chemical_melting_point          413
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.20170(10)
_cell_length_b                   7.959
_cell_length_c                   25.92590(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2517.75(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    27162
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      73.7760
_cell_measurement_theta_min      3.9780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76993
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.2c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            44648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.070
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector_area_resol_mean 5.2387
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
__diffrn_measurement_device      'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2479
_reflns_number_total             2550
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00073(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.091
_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)+(0.0402P)²+1.3032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0881
_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
2. Others
 Fixed Sof: O2B(0.5) O3A(0.5) O3B(0.5) O2A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.75358(4) -0.23102(6) 0.27172(2) 0.05126(16) Uani 1 1 d . . . . .
Cl2 Cl 0.71434(4) 0.04975(6) 0.08492(2) 0.04760(15) Uani 1 1 d . . . . .
C1 C 0.48377(13) 0.15643(19) 0.11777(6) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.55166(12) 0.05583(17) 0.15590(6) 0.0307(3) Uani 1 1 d . . . . .
C7 C 0.50806(14) 0.0119(2) 0.20368(6) 0.0365(4) Uani 1 1 d . . . . .
H7 H 0.436846 0.044044 0.211819 0.044 Uiso 1 1 calc R . . . .
C6 C 0.56861(14) -0.0785(2) 0.23931(6) 0.0387(4) Uani 1 1 d . . . . .
H6 H 0.538787 -0.107671 0.271091 0.046 Uiso 1 1 calc R . . . .
C5 C 0.67419(14) -0.12446(19) 0.22656(6) 0.0353(3) Uani 1 1 d . . . . .
C4 C 0.72054(13) -0.0871(2) 0.17947(6) 0.0349(3) Uani 1 1 d . . . . .
H4 H 0.791342 -0.121215 0.171324 0.042 Uiso 1 1 calc R . . . .
C3 C 0.65760(13) 0.00340(19) 0.14472(6) 0.0321(3) Uani 1 1 d . . . . .
O1 O 0.38529(10) 0.46455(13) 0.05305(5) 0.0388(3) Uani 1 1 d . . . . .
N1 N 0.39692(11) 0.63796(15) 0.06414(5) 0.0304(3) Uani 1 1 d . . . . .
C10 C 0.34530(17) 0.6755(2) 0.11449(7) 0.0474(4) Uani 1 1 d . . . . .
H10A H 0.269252 0.644839 0.113378 0.071 Uiso 1 1 calc GR . . . .
H10B H 0.351712 0.793462 0.121650 0.071 Uiso 1 1 calc GR . . . .
H10C H 0.381467 0.612649 0.141117 0.071 Uiso 1 1 calc GR . . . .
C8 C 0.51455(15) 0.6831(2) 0.06465(8) 0.0492(4) Uani 1 1 d . . . . .
H8A H 0.550601 0.624522 0.092219 0.074 Uiso 1 1 calc GR . . . .
H8B H 0.522085 0.802002 0.069691 0.074 Uiso 1 1 calc GR . . . .
H8C H 0.547297 0.651950 0.032361 0.074 Uiso 1 1 calc GR . . . .
C9 C 0.3387(2) 0.7264(2) 0.02224(7) 0.0590(6) Uani 1 1 d . . . . .
H9A H 0.371160 0.697279 -0.010293 0.089 Uiso 1 1 calc GR . . . .
H9B H 0.344265 0.845500 0.027464 0.089 Uiso 1 1 calc GR . . . .
H9C H 0.262974 0.693899 0.022308 0.089 Uiso 1 1 calc GR . . . .
O2B O 0.4818(12) 0.315(2) 0.1251(6) 0.040(2) Uani 0.5 1 d . . P . .
O3A O 0.4314(13) 0.088(2) 0.0827(8) 0.059(4) Uani 0.5 1 d . . P . .
O3B O 0.4186(11) 0.076(2) 0.0920(7) 0.044(2) Uani 0.5 1 d . . P . .
O2A O 0.5048(13) 0.312(3) 0.1169(6) 0.046(2) Uani 0.5 1 d . . P . .
H1 H 0.429(2) 0.398(4) 0.0809(11) 0.092(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.7404(15) . ?
Cl2 C3 1.7377(16) . ?
C1 C2 1.518(2) . ?
C1 O2B 1.273(19) . ?
C1 O3A 1.238(18) . ?
C1 O3B 1.220(15) . ?
C1 O2A 1.26(2) . ?
C2 C7 1.393(2) . ?
C2 C3 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.379(2) . ?
C5 C4 1.378(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(2) . ?
O1 N1 1.4169(15) . ?
O1 H1 1.04(3) . ?
N1 C10 1.480(2) . ?
N1 C8 1.480(2) . ?
N1 C9 1.476(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2B H1 1.47(4) . ?
O2A H1 1.48(3) . ?

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
O2B C1 C2 115.7(8) . . ?
O3A C1 C2 121.7(8) . . ?
O3A C1 O2B 122.5(11) . . ?
O3A C1 O2A 121.6(12) . . ?
O3B C1 C2 115.8(7) . . ?
O3B C1 O2B 126.1(10) . . ?
O3B C1 O3A 14.1(19) . . ?
O3B C1 O2A 129.5(11) . . ?
O2A C1 C2 114.7(9) . . ?
O2A C1 O2B 16.0(10) . . ?
C7 C2 C1 120.21(14) . . ?
C3 C2 C1 122.03(14) . . ?
C3 C2 C7 117.76(14) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.33(15) . . ?
C6 C7 H7 119.3 . . ?
C7 C6 H6 120.8 . . ?
C5 C6 C7 118.43(15) . . ?
C5 C6 H6 120.8 . . ?
C6 C5 Cl1 119.19(13) . . ?
C4 C5 Cl1 118.23(13) . . ?
C4 C5 C6 122.58(14) . . ?
C5 C4 H4 121.3 . . ?
C5 C4 C3 117.44(15) . . ?
C3 C4 H4 121.3 . . ?
C2 C3 Cl2 119.55(12) . . ?
C4 C3 Cl2 118.01(12) . . ?
C4 C3 C2 122.43(15) . . ?
N1 O1 H1 107.5(16) . . ?
O1 N1 C10 109.46(12) . . ?
O1 N1 C8 109.59(12) . . ?
O1 N1 C9 105.49(12) . . ?
C8 N1 C10 110.85(14) . . ?
C9 N1 C10 110.37(14) . . ?
C9 N1 C8 110.94(16) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 O2B H1 109.7(17) . . ?
C1 O2A H1 109.9(18) . . ?

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
Cl1 C5 C4 C3 -177.60(12) . . . . ?
C1 C2 C7 C6 -179.45(15) . . . . ?
C1 C2 C3 Cl2 -1.3(2) . . . . ?
C1 C2 C3 C4 179.37(14) . . . . ?
C2 C7 C6 C5 0.2(2) . . . . ?
C7 C2 C3 Cl2 178.17(12) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C7 C6 C5 Cl1 177.50(13) . . . . ?
C7 C6 C5 C4 -1.5(2) . . . . ?
C6 C5 C4 C3 1.4(2) . . . . ?
C5 C4 C3 Cl2 -179.36(12) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
O2B C1 C2 C7 81.8(6) . . . . ?
O2B C1 C2 C3 -98.7(6) . . . . ?
O3A C1 C2 C7 -96.2(11) . . . . ?
O3A C1 C2 C3 83.3(11) . . . . ?
O3B C1 C2 C7 -81.7(11) . . . . ?
O3B C1 C2 C3 97.8(11) . . . . ?
O2A C1 C2 C7 99.5(6) . . . . ?
O2A C1 C2 C3 -81.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_TMNO24DCB295K
_database_code_depnum_ccdc_archive 'CCDC 1545109'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 Cl2 O2, C3 H10 N O'
_chemical_formula_sum            'C10 H13 Cl2 N O3'
_chemical_formula_weight         266.11
_chemical_melting_point          413
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.27690(10)
_cell_length_b                   8.00180(10)
_cell_length_c                   26.0006(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2554.23(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23315
_cell_measurement_temperature    294.87(10)
_cell_measurement_theta_max      73.4300
_cell_measurement_theta_min      4.9270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  0.439
_exptl_absorpt_correction_T_min  0.143
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            44547
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.129
_diffrn_reflns_theta_min         3.400
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.87(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2387
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2474
_reflns_number_total             2586
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.066
_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)+(0.0546P)²+0.9422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1137
_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
2. Others
 Fixed Sof: Cl1A(0.5) O3A(0.5) O2A(0.5) O3B(0.5) O2B(0.5) Cl1B(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.7592(9) -0.2214(12) 0.2698(4) 0.0728(13) Uani 0.5 1 d . . P . .
Cl2 Cl 0.71502(5) 0.05393(8) 0.08512(2) 0.0783(2) Uani 1 1 d . . . . .
O3A O 0.4421(11) 0.091(3) 0.0819(8) 0.080(3) Uani 0.5 1 d . . P A 2
C1 C 0.48549(15) 0.1626(2) 0.11729(7) 0.0547(4) Uani 1 1 d . . . . .
C2 C 0.55285(14) 0.06424(19) 0.15546(7) 0.0500(4) Uani 1 1 d . . . . .
C7 C 0.50961(17) 0.0224(2) 0.20322(8) 0.0586(5) Uani 1 1 d . . . . .
H7 H 0.438830 0.054875 0.211149 0.070 Uiso 1 1 calc R . . . .
C6 C 0.56912(18) -0.0660(2) 0.23913(8) 0.0617(5) Uani 1 1 d . . . . .
H6 H 0.539271 -0.093226 0.270913 0.074 Uiso 1 1 calc R . . . .
C5 C 0.67384(17) -0.1128(2) 0.22668(7) 0.0572(4) Uani 1 1 d . . . . .
C4 C 0.71990(15) -0.0773(2) 0.17977(8) 0.0571(4) Uani 1 1 d . . . . .
H4 H 0.790313 -0.111663 0.171871 0.069 Uiso 1 1 calc R . . . .
C3 C 0.65794(15) 0.0112(2) 0.14473(7) 0.0520(4) Uani 1 1 d . . . . .
O1 O 0.38561(13) 0.47041(14) 0.05359(5) 0.0620(4) Uani 1 1 d . . . . .
N1 N 0.39754(12) 0.64254(16) 0.06454(5) 0.0490(3) Uani 1 1 d . . . . .
C10 C 0.3485(2) 0.6799(3) 0.11496(9) 0.0822(7) Uani 1 1 d . . . . .
H10A H 0.389119 0.624329 0.141486 0.123 Uiso 1 1 calc GR . . . .
H10B H 0.274482 0.641291 0.115444 0.123 Uiso 1 1 calc GR . . . .
H10C H 0.350004 0.798303 0.120808 0.123 Uiso 1 1 calc GR . . . .
C9 C 0.3372(3) 0.7292(3) 0.02358(10) 0.0977(10) Uani 1 1 d . . . . .
H9A H 0.262197 0.695148 0.024392 0.146 Uiso 1 1 calc GR . . . .
H9B H 0.368153 0.701289 -0.009205 0.146 Uiso 1 1 calc GR . . . .
H9C H 0.341713 0.847759 0.028842 0.146 Uiso 1 1 calc GR . . . .
C8 C 0.5134(2) 0.6876(3) 0.06345(12) 0.0857(7) Uani 1 1 d . . . . .
H8A H 0.544154 0.655798 0.030948 0.129 Uiso 1 1 calc GR . . . .
H8B H 0.550880 0.630296 0.090644 0.129 Uiso 1 1 calc GR . . . .
H8C H 0.520918 0.806034 0.068059 0.129 Uiso 1 1 calc GR . . . .
O2A O 0.5081(9) 0.3161(18) 0.1147(5) 0.069(2) Uani 0.5 1 d . . P A 1
O3B O 0.4141(11) 0.086(2) 0.0929(7) 0.071(3) Uani 0.5 1 d . . P A .
O2B O 0.4801(9) 0.3192(19) 0.1255(5) 0.066(2) Uani 0.5 1 d . . P A .
H1 H 0.429(3) 0.407(4) 0.0803(12) 0.120(11) Uiso 1 1 d . . . . .
Cl1B Cl 0.7439(10) -0.2106(13) 0.2753(4) 0.0843(18) Uani 0.5 1 d . . 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
Cl1A C5 1.763(10) . ?
Cl2 C3 1.7350(19) . ?
O3A C1 1.21(2) . ?
C1 C2 1.513(2) . ?
C1 O2A 1.261(15) . ?
C1 O3B 1.242(19) . ?
C1 O2B 1.273(15) . ?
C2 C7 1.391(3) . ?
C2 C3 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.378(3) . ?
C5 C4 1.374(3) . ?
C5 Cl1B 1.719(10) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(3) . ?
O1 N1 1.4141(17) . ?
O1 H1 1.02(3) . ?
N1 C10 1.473(2) . ?
N1 C9 1.471(3) . ?
N1 C8 1.467(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
O3A C1 C2 119.6(10) . . ?
O3A C1 O3B 21.0(11) . . ?
O3A C1 O2B 124.9(12) . . ?
O2A C1 C2 114.9(7) . . ?
O2A C1 O2B 20.1(7) . . ?
O3B C1 C2 117.7(9) . . ?
O3B C1 O2A 127.3(11) . . ?
O3B C1 O2B 122.1(11) . . ?
O2B C1 C2 115.5(7) . . ?
C7 C2 C1 120.13(16) . . ?
C3 C2 C1 122.41(17) . . ?
C3 C2 C7 117.45(16) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.66(18) . . ?
C6 C7 H7 119.2 . . ?
C7 C6 H6 120.8 . . ?
C5 C6 C7 118.32(19) . . ?
C5 C6 H6 120.8 . . ?
C6 C5 Cl1A 122.6(4) . . ?
C6 C5 Cl1B 114.7(4) . . ?
C4 C5 Cl1A 114.9(4) . . ?
C4 C5 C6 122.43(17) . . ?
C4 C5 Cl1B 122.8(4) . . ?
Cl1B C5 Cl1A 8.2(7) . . ?
C5 C4 H4 121.2 . . ?
C5 C4 C3 117.68(17) . . ?
C3 C4 H4 121.2 . . ?
C2 C3 Cl2 119.68(14) . . ?
C4 C3 Cl2 117.88(15) . . ?
C4 C3 C2 122.44(18) . . ?
N1 O1 H1 107.2(19) . . ?
O1 N1 C10 109.53(15) . . ?
O1 N1 C9 105.14(15) . . ?
O1 N1 C8 109.61(15) . . ?
C9 N1 C10 110.04(19) . . ?
C8 N1 C10 111.31(18) . . ?
C8 N1 C9 111.0(2) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
Cl1A C5 C4 C3 -178.5(4) . . . . ?
O3A C1 C2 C7 -101.4(7) . . . . ?
O3A C1 C2 C3 78.0(7) . . . . ?
C1 C2 C7 C6 -179.46(17) . . . . ?
C1 C2 C3 Cl2 -1.3(2) . . . . ?
C1 C2 C3 C4 179.38(17) . . . . ?
C2 C7 C6 C5 0.0(3) . . . . ?
C7 C2 C3 Cl2 178.10(14) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C6 C5 Cl1A 178.4(4) . . . . ?
C7 C6 C5 C4 -1.2(3) . . . . ?
C7 C6 C5 Cl1B 176.1(4) . . . . ?
C6 C5 C4 C3 1.1(3) . . . . ?
C5 C4 C3 Cl2 -179.16(14) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
O2A C1 C2 C7 101.3(5) . . . . ?
O2A C1 C2 C3 -79.3(5) . . . . ?
O3B C1 C2 C7 -77.5(8) . . . . ?
O3B C1 C2 C3 101.9(8) . . . . ?
O2B C1 C2 C7 79.0(5) . . . . ?
O2B C1 C2 C3 -101.5(5) . . . . ?
Cl1B C5 C4 C3 -176.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_TMANO24DCB_250K
_database_code_depnum_ccdc_archive 'CCDC 1545107'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 Cl2 N O3'
_chemical_formula_sum            'C10 H13 Cl2 N O3'
_chemical_formula_weight         266.11
_chemical_melting_point          413
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.24030(10)
_cell_length_b                   7.97880(10)
_cell_length_c                   25.9695(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2536.26(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    24211
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      73.7470
_cell_measurement_theta_min      3.9650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70074
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.2c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            45068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.861
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2387
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2471
_reflns_number_total             2564
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00111(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.077
_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)+(0.0435P)²+1.0050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0933
_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
2. Others
 Fixed Sof: Cl1B(0.5) O2A(0.5) O3B(0.5) O3A(0.5) O2B(0.5) Cl1A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1B Cl 0.2576(7) -0.2271(10) 0.2697(3) 0.0589(10) Uani 0.5 1 d . . P A 1
Cl2 Cl 0.21465(4) 0.05194(7) 0.08507(2) 0.06156(17) Uani 1 1 d . . . . .
C1 C -0.01547(13) 0.15948(19) 0.11755(6) 0.0430(4) Uani 1 1 d . . . . .
C2 C 0.05222(13) 0.06015(17) 0.15569(6) 0.0390(3) Uani 1 1 d . . . . .
C7 C 0.00889(14) 0.0172(2) 0.20341(7) 0.0461(4) Uani 1 1 d . . . . .
H7 H -0.062110 0.049421 0.211447 0.055 Uiso 1 1 calc R . . . .
C6 C 0.06879(15) -0.0723(2) 0.23918(7) 0.0489(4) Uani 1 1 d . . . . .
H6 H 0.038809 -0.100631 0.270912 0.059 Uiso 1 1 calc R . . . .
C5 C 0.17398(14) -0.11842(19) 0.22673(6) 0.0448(4) Uani 1 1 d . . . . .
C4 C 0.22008(13) -0.0819(2) 0.17961(6) 0.0449(4) Uani 1 1 d . . . . .
H4 H 0.290673 -0.116190 0.171589 0.054 Uiso 1 1 calc R . . . .
C3 C 0.15777(13) 0.00735(19) 0.14470(6) 0.0406(3) Uani 1 1 d . . . . .
O1 O -0.11448(11) 0.46741(13) 0.05331(5) 0.0492(3) Uani 1 1 d . . . . .
N1 N -0.10274(11) 0.64038(14) 0.06432(5) 0.0383(3) Uani 1 1 d . . . . .
C10 C -0.15321(19) 0.6778(3) 0.11474(7) 0.0624(5) Uani 1 1 d . . . . .
H10A H -0.228128 0.642141 0.114487 0.094 Uiso 1 1 calc GR . . . .
H10B H -0.149861 0.796161 0.121117 0.094 Uiso 1 1 calc GR . . . .
H10C H -0.114434 0.619233 0.141374 0.094 Uiso 1 1 calc GR . . . .
C8 C 0.01394(16) 0.6854(3) 0.06417(9) 0.0650(5) Uani 1 1 d . . . . .
H8A H 0.050497 0.627800 0.091677 0.097 Uiso 1 1 calc GR . . . .
H8B H 0.021460 0.804171 0.068864 0.097 Uiso 1 1 calc GR . . . .
H8C H 0.045931 0.653519 0.031869 0.097 Uiso 1 1 calc GR . . . .
O2A O 0.0066(10) 0.3144(19) 0.1157(5) 0.056(2) Uani 0.5 1 d . . P . .
O3B O -0.0819(11) 0.082(2) 0.0928(6) 0.056(2) Uani 0.5 1 d . . P . .
O3A O -0.0649(13) 0.089(2) 0.0819(7) 0.072(4) Uani 0.5 1 d . . P . .
O2B O -0.0193(10) 0.3164(19) 0.1254(5) 0.052(2) Uani 0.5 1 d . . P . .
Cl1A Cl 0.2471(7) -0.2185(10) 0.2748(4) 0.0682(14) Uani 0.5 1 d . . P A 2
C9 C -0.1620(2) 0.7278(2) 0.02284(8) 0.0769(7) Uani 1 1 d . . . . .
H9A H -0.130515 0.698616 -0.009809 0.115 Uiso 1 1 calc GR . . . .
H9B H -0.156630 0.846664 0.027921 0.115 Uiso 1 1 calc GR . . . .
H9C H -0.237444 0.694949 0.023398 0.115 Uiso 1 1 calc GR . . . .
H1 H -0.068(2) 0.400(4) 0.0803(11) 0.112(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1B C5 1.746(9) . ?
Cl2 C3 1.7348(16) . ?
C1 C2 1.515(2) . ?
C1 O2A 1.266(15) . ?
C1 O3B 1.208(14) . ?
C1 O3A 1.243(17) . ?
C1 O2B 1.270(15) . ?
C2 C7 1.391(2) . ?
C2 C3 1.389(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.382(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.378(3) . ?
C5 C4 1.379(2) . ?
C5 Cl1A 1.731(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(2) . ?
O1 N1 1.4167(15) . ?
O1 H1 1.05(3) . ?
N1 C10 1.478(2) . ?
N1 C8 1.473(2) . ?
N1 C9 1.474(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O2A H1 1.47(3) . ?
O2B H1 1.48(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
O2A C1 C2 114.7(7) . . ?
O2A C1 O2B 18.4(7) . . ?
O3B C1 C2 116.6(7) . . ?
O3B C1 O2A 128.7(10) . . ?
O3B C1 O3A 16.6(16) . . ?
O3B C1 O2B 124.5(10) . . ?
O3A C1 C2 121.1(8) . . ?
O3A C1 O2A 121.3(11) . . ?
O3A C1 O2B 123.3(11) . . ?
O2B C1 C2 115.6(7) . . ?
C7 C2 C1 120.19(14) . . ?
C3 C2 C1 122.23(14) . . ?
C3 C2 C7 117.58(14) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.59(16) . . ?
C6 C7 H7 119.2 . . ?
C7 C6 H6 120.8 . . ?
C5 C6 C7 118.43(16) . . ?
C5 C6 H6 120.8 . . ?
C6 C5 Cl1B 122.1(3) . . ?
C6 C5 C4 122.30(15) . . ?
C6 C5 Cl1A 116.0(3) . . ?
C4 C5 Cl1B 115.6(3) . . ?
C4 C5 Cl1A 121.7(3) . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C3 117.72(15) . . ?
C3 C4 H4 121.1 . . ?
C2 C3 Cl2 119.64(12) . . ?
C4 C3 Cl2 118.01(13) . . ?
C4 C3 C2 122.34(15) . . ?
N1 O1 H1 108.0(17) . . ?
O1 N1 C10 109.45(13) . . ?
O1 N1 C8 109.59(13) . . ?
O1 N1 C9 105.27(12) . . ?
C8 N1 C10 111.01(15) . . ?
C8 N1 C9 111.10(17) . . ?
C9 N1 C10 110.26(16) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 O2A H1 110.2(16) . . ?
C1 O2B H1 109.6(15) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Cl1B C5 C4 C3 -178.6(3) . . . . ?
C1 C2 C7 C6 -179.52(15) . . . . ?
C1 C2 C3 Cl2 -1.2(2) . . . . ?
C1 C2 C3 C4 179.37(15) . . . . ?
C2 C7 C6 C5 0.3(3) . . . . ?
C7 C2 C3 Cl2 178.13(12) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
C7 C6 C5 Cl1B 178.4(3) . . . . ?
C7 C6 C5 C4 -1.6(3) . . . . ?
C7 C6 C5 Cl1A 176.1(3) . . . . ?
C6 C5 C4 C3 1.4(2) . . . . ?
C5 C4 C3 Cl2 -179.35(12) . . . . ?
C5 C4 C3 C2 0.0(2) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
O2A C1 C2 C7 100.6(5) . . . . ?
O2A C1 C2 C3 -80.0(5) . . . . ?
O3B C1 C2 C7 -80.0(10) . . . . ?
O3B C1 C2 C3 99.3(10) . . . . ?
O3A C1 C2 C7 -98.3(10) . . . . ?
O3A C1 C2 C3 81.0(10) . . . . ?
O2B C1 C2 C7 80.4(5) . . . . ?
O2B C1 C2 C3 -100.3(5) . . . . ?
Cl1A C5 C4 C3 -176.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_TMAO24DCB_100K
_database_code_depnum_ccdc_archive 'CCDC 1545108'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 Cl1.98 O2, C3 H10 N O'
_chemical_formula_sum            'C10 H13 Cl1.98 N O3'
_chemical_formula_weight         265.40
_chemical_melting_point          413
_chemical_oxdiff_formula         'C20 H26 Cl4 N2 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.12852(10)
_cell_length_b                   7.92362(7)
_cell_length_c                   25.81707(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2481.07(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    30156
_cell_measurement_temperature    99.98(18)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      4.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.626
_exptl_absorpt_correction_T_max  0.645
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41t (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1101
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 0 -2 0.0981
3 -1 15 0.0477
-4 -4 1 0.2102
4 4 -3 0.1332
3 -5 -1 0.1271
-2 5 0 0.0914
-8 -1 2 0.1329
-2 1 -15 0.0650

_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.7787 0.4943 -2.0222 0.1821 0.7690 0.6128
2.6266 -1.0823 15.3969 0.9943 0.0795 -0.0706
-4.2629 -4.3205 0.6261 -0.0407 -0.0006 -0.9992
3.7058 4.4210 -3.3480 -0.1368 -0.0136 0.9905
3.3976 -4.6364 -0.6090 0.1983 0.8238 -0.5310
-1.5548 5.0425 0.1136 -0.1623 -0.6707 0.7237
-7.7613 -0.5994 2.0237 -0.1790 -0.7566 -0.6289
-2.4629 1.2414 -15.3923 -0.9910 -0.0793 0.1078

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            43582
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.071
_diffrn_reflns_theta_min         5.004
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2387
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -42.35 125.00  60.00   94
  2  ω   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00 -60.00   96
  3  ω     23.00  97.00   1.00    1.00    --   42.35-125.00-150.00   74
  4  ω     83.00 178.00   1.00    2.00    --  106.34  30.00-150.00   95
  5  ω     26.00 109.00   1.00    2.00    --  106.34 -95.00-120.00   83
  6  ω     32.00 130.00   1.00    2.00    --  106.34 -30.00-150.00   98
  7  ω     94.00 178.00   1.00    2.00    --  106.34 125.00 120.00   84
  8  ω     35.00 121.00   1.00    2.00    --  106.34-125.00  90.00   86
  9  ω     35.00 130.00   1.00    2.00    --  106.34 -45.00  30.00   95
 10  ω   -113.00 -58.00   1.00    1.00    --  -42.35-148.00 137.00   55
 11  ω   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00-180.00   96
 12  ω   -112.00 -16.00   1.00    1.00    --  -42.35 -57.00  60.00   96
 13  ω     83.00 178.00   1.00    2.00    --  106.34  30.00 -90.00   95
 14  ω     61.00 178.00   1.00    2.00    --  106.34  15.00 120.00  117
 15  ω     75.00 178.00   1.00    2.00    --  106.34  77.00 -60.00  103
 16  ω     82.00 178.00   1.00    2.00    --  106.34  45.00  30.00   96
 17  ω     82.00 178.00   1.00    2.00    --  106.34  45.00 150.00   96
 18  ω     83.00 178.00   1.00    2.00    --  106.34  30.00   0.00   95
 19  ω   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00-120.00  105
 20  ω   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00   0.00  105
 21  ω    -65.00  30.00   1.00    1.00    --  -42.35  38.00  30.00   95
 22  ω     75.00 178.00   1.00    2.00    --  106.34  77.00 -90.00  103
 23  ω     75.00 178.00   1.00    2.00    --  106.34  77.00  90.00  103
 24  ω     79.00 177.00   1.00    2.00    --  106.34  61.00-150.00   98
 25  ω     75.00 178.00   1.00    2.00    --  106.34  77.00 -30.00  103
 26  ω     79.00 177.00   1.00    2.00    --  106.34  61.00  60.00   98
 27  ω     26.00 109.00   1.00    2.00    --  106.34 -95.00 150.00   83
 28  ω   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00 150.00  105
 29  ω   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00 -90.00  105
 30  ω   -116.00 -11.00   1.00    1.00    --  -42.35 -77.00  60.00  105
 31  ω     75.00 134.00   1.00    2.00    --  106.34  77.00-120.00   59
 32  ω     75.00 178.00   1.00    2.00    --  106.34  77.00 150.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0394093000
_diffrn_orient_matrix_UB_12      -0.0213002000
_diffrn_orient_matrix_UB_13      0.0563594000
_diffrn_orient_matrix_UB_21      0.1003503000
_diffrn_orient_matrix_UB_22      -0.1016455000
_diffrn_orient_matrix_UB_23      -0.0191000000
_diffrn_orient_matrix_UB_31      0.0671679000
_diffrn_orient_matrix_UB_32      0.1643380000
_diffrn_orient_matrix_UB_33      -0.0044956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2473
_reflns_number_total             2505
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41t (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.095
_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)+(0.0290P)²+1.5560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0697
_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
2. Others
 Fixed Sof: Cl1B(0.58094) Cl1A(0.39881)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.21426(3) 0.04638(5) 0.41538(2) 0.02746(12) Uani 1 1 d . . . . .
Cl1B Cl 0.2549(2) -0.2462(5) 0.22933(14) 0.0210(6) Uani 0.5809 1 d . . P A 2
O1 O -0.11505(9) 0.46061(12) 0.44721(4) 0.0246(2) Uani 1 1 d . . . . .
N1 N -0.10324(9) 0.63523(14) 0.43618(4) 0.0201(2) Uani 1 1 d . . . . .
O3 O -0.07716(10) 0.07613(14) 0.41246(4) 0.0334(3) Uani 1 1 d . . . . .
O2 O -0.00695(9) 0.31053(13) 0.37781(4) 0.0318(3) Uani 1 1 d . . . . .
C4 C 0.22144(11) -0.09515(18) 0.32087(5) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.292586 -0.129196 0.329316 0.026 Uiso 1 1 calc R . . . .
C6 C 0.06831(12) -0.08844(18) 0.26032(5) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.038446 -0.118462 0.228446 0.029 Uiso 1 1 calc R . . . .
C1 C -0.01706(11) 0.15197(17) 0.38180(5) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.05101(11) 0.04970(16) 0.34375(5) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.17481(12) -0.13459(17) 0.27338(5) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.15761(11) -0.00279(17) 0.35529(5) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.00704(12) 0.00377(18) 0.29593(5) 0.0225(3) Uani 1 1 d . . . . .
H7 H -0.064680 0.035434 0.287677 0.027 Uiso 1 1 calc R . . . .
C8 C -0.15663(13) 0.67344(19) 0.38572(5) 0.0277(3) Uani 1 1 d . . . . .
H8A H -0.120686 0.610875 0.358725 0.042 Uiso 1 1 calc GR . . . .
H8B H -0.150671 0.792042 0.378653 0.042 Uiso 1 1 calc GR . . . .
H8C H -0.233026 0.642109 0.387186 0.042 Uiso 1 1 calc GR . . . .
C10 C 0.01571(12) 0.68042(19) 0.43496(6) 0.0279(3) Uani 1 1 d . . . . .
H10A H 0.049522 0.648836 0.467152 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.023293 0.799904 0.429927 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.051125 0.621713 0.407008 0.042 Uiso 1 1 calc GR . . . .
C9 C -0.16021(15) 0.7249(2) 0.47880(6) 0.0348(4) Uani 1 1 d . . . . .
H9A H -0.236747 0.694007 0.479021 0.052 Uiso 1 1 calc GR . . . .
H9B H -0.153570 0.844469 0.473746 0.052 Uiso 1 1 calc GR . . . .
H9C H -0.127233 0.694245 0.511274 0.052 Uiso 1 1 calc GR . . . .
H1 H -0.069(2) 0.397(3) 0.4196(9) 0.074(8) Uiso 1 1 d . . . . .
Cl1A Cl 0.2549(5) -0.2360(9) 0.2269(2) 0.0395(16) Uani 0.3988 1 d . . P A 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
Cl2 C3 1.7408(14) . ?
Cl1B C5 1.738(4) . ?
O1 N1 1.4198(14) . ?
N1 C8 1.4859(17) . ?
N1 C10 1.4869(18) . ?
N1 C9 1.4808(17) . ?
O3 C1 1.2326(17) . ?
O2 C1 1.2665(18) . ?
C4 C5 1.3858(19) . ?
C4 C3 1.3872(19) . ?
C6 C5 1.384(2) . ?
C6 C7 1.390(2) . ?
C1 C2 1.5176(18) . ?
C2 C3 1.3905(19) . ?
C2 C7 1.3933(19) . ?
C5 Cl1A 1.741(7) . ?

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 C8 109.30(10) . . ?
O1 N1 C10 109.69(10) . . ?
O1 N1 C9 105.74(10) . . ?
C8 N1 C10 110.80(11) . . ?
C9 N1 C8 110.51(12) . . ?
C9 N1 C10 110.67(12) . . ?
C5 C4 C3 117.25(13) . . ?
C5 C6 C7 118.47(13) . . ?
O3 C1 O2 126.38(13) . . ?
O3 C1 C2 118.50(12) . . ?
O2 C1 C2 115.11(12) . . ?
C3 C2 C1 121.80(12) . . ?
C3 C2 C7 117.88(12) . . ?
C7 C2 C1 120.32(12) . . ?
C4 C5 Cl1B 117.75(14) . . ?
C4 C5 Cl1A 119.1(2) . . ?
C6 C5 Cl1B 119.78(14) . . ?
C6 C5 C4 122.47(13) . . ?
C6 C5 Cl1A 118.4(2) . . ?
C4 C3 Cl2 117.95(11) . . ?
C4 C3 C2 122.65(13) . . ?
C2 C3 Cl2 119.41(10) . . ?
C6 C7 C2 121.25(13) . . ?

_olex2_date_sample_data_collection 2016-02-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_TMANO24DCB150K
_database_code_depnum_ccdc_archive 'CCDC 1545106'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
_audit_creation_date             2017-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H3 Cl2 O2, C3 H10 N O'
_chemical_formula_sum            'C10 H13 Cl2 N O3'
_chemical_formula_weight         266.11
_chemical_melting_point          413
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.16200(10)
_cell_length_b                   7.94030(10)
_cell_length_c                   25.8738(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2498.63(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28976
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      73.7470
_cell_measurement_theta_min      4.0010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.634
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.2c (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            44199
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.013
_diffrn_reflns_theta_min         3.416
_diffrn_ambient_temperature      150(10)
_diffrn_ambient_environment      N~2~
_diffrn_detector_area_resol_mean 5.2387
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401807000
_diffrn_orient_matrix_UB_12      0.0255179000
_diffrn_orient_matrix_UB_13      0.0559284000
_diffrn_orient_matrix_UB_21      -0.0989781000
_diffrn_orient_matrix_UB_22      0.1018579000
_diffrn_orient_matrix_UB_23      -0.0200879000
_diffrn_orient_matrix_UB_31      -0.0681052000
_diffrn_orient_matrix_UB_32      -0.1630971000
_diffrn_orient_matrix_UB_33      -0.0037800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2476
_reflns_number_total             2527
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.2c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.086
_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)+(0.0356P)²+1.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0781
_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
2. Others
 Fixed Sof: O3B(0.5) O2B(0.5) O3A(0.5) O2A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.75439(3) -0.23733(5) 0.27157(2) 0.03986(13) Uani 1 1 d . . . . .
Cl2 Cl 0.71423(3) 0.04787(5) 0.08477(2) 0.03711(13) Uani 1 1 d . . . . .
C1 C 0.48321(12) 0.15378(18) 0.11798(6) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.55126(11) 0.05231(16) 0.15606(5) 0.0252(3) Uani 1 1 d . . . . .
C3 C 0.65753(12) -0.00008(17) 0.14471(5) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.72086(12) -0.09139(18) 0.17933(6) 0.0282(3) Uani 1 1 d . . . . .
H4 H 0.7919 -0.1254 0.1711 0.034 Uiso 1 1 calc R . . . .
C5 C 0.67448(12) -0.12997(18) 0.22654(5) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.56835(13) -0.08385(18) 0.23951(6) 0.0314(3) Uani 1 1 d . . . . .
H6 H 0.5385 -0.1133 0.2714 0.038 Uiso 1 1 calc R . . . .
C7 C 0.50749(13) 0.00730(18) 0.20389(6) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.4360 0.0391 0.2121 0.035 Uiso 1 1 calc R . . . .
O1 O 0.38508(9) 0.46227(12) 0.05290(4) 0.0312(2) Uani 1 1 d . . . . .
N1 N 0.39681(10) 0.63623(14) 0.06397(4) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.51508(13) 0.6813(2) 0.06494(7) 0.0375(4) Uani 1 1 d . . . . .
H8A H 0.5506 0.6235 0.0929 0.056 Uiso 1 1 calc GR . . . .
H8B H 0.5226 0.8007 0.0697 0.056 Uiso 1 1 calc GR . . . .
H8C H 0.5486 0.6490 0.0328 0.056 Uiso 1 1 calc GR . . . .
C9 C 0.33930(18) 0.7254(2) 0.02166(6) 0.0461(5) Uani 1 1 d . . . . .
H9A H 0.3717 0.6948 -0.0108 0.069 Uiso 1 1 calc GR . . . .
H9B H 0.3459 0.8447 0.0267 0.069 Uiso 1 1 calc GR . . . .
H9C H 0.2630 0.6944 0.0217 0.069 Uiso 1 1 calc GR . . . .
C10 C 0.34419(14) 0.6742(2) 0.11437(6) 0.0370(4) Uani 1 1 d . . . . .
H10A H 0.2680 0.6426 0.1131 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.3500 0.7925 0.1214 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.3805 0.6119 0.1412 0.055 Uiso 1 1 calc GR . . . .
O3B O 0.4191(14) 0.075(3) 0.0912(10) 0.0347(19) Uani 0.5 1 d . . P . .
O2B O 0.4814(10) 0.310(2) 0.1247(6) 0.0307(17) Uani 0.5 1 d . . P . .
O3A O 0.4287(16) 0.082(3) 0.0837(10) 0.047(4) Uani 0.5 1 d . . P . .
O2A O 0.5046(10) 0.313(2) 0.1185(6) 0.035(2) Uani 0.5 1 d . . P . .
H1 H 0.429(2) 0.400(3) 0.0803(9) 0.077(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.7402(14) . ?
Cl2 C3 1.7396(14) . ?
C1 C2 1.5182(19) . ?
C1 O3B 1.215(19) . ?
C1 O2B 1.253(17) . ?
C1 O3A 1.25(2) . ?
C1 O2A 1.293(17) . ?
C2 C3 1.389(2) . ?
C2 C7 1.394(2) . ?
C3 C4 1.386(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(2) . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9300 . ?
O1 N1 1.4179(14) . ?
O1 H1 1.02(3) . ?
N1 C8 1.4826(19) . ?
N1 C9 1.4794(18) . ?
N1 C10 1.4833(18) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
O3B C1 C2 116.7(9) . . ?
O3B C1 O2B 125.1(11) . . ?
O3B C1 O3A 11(2) . . ?
O3B C1 O2A 129.6(12) . . ?
O2B C1 C2 116.4(7) . . ?
O2B C1 O2A 14.6(10) . . ?
O3A C1 C2 120.7(10) . . ?
O3A C1 O2B 122.8(12) . . ?
O3A C1 O2A 124.3(13) . . ?
O2A C1 C2 113.7(7) . . ?
C3 C2 C1 121.93(13) . . ?
C3 C2 C7 117.79(13) . . ?
C7 C2 C1 120.27(13) . . ?
C2 C3 Cl2 119.45(11) . . ?
C4 C3 Cl2 118.06(11) . . ?
C4 C3 C2 122.48(13) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.46(13) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 Cl1 118.24(11) . . ?
C4 C5 C6 122.51(13) . . ?
C6 C5 Cl1 119.24(11) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.38(14) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.36(14) . . ?
C6 C7 H7 119.3 . . ?
N1 O1 H1 106.3(15) . . ?
O1 N1 C8 109.65(11) . . ?
O1 N1 C9 105.61(11) . . ?
O1 N1 C10 109.39(11) . . ?
C8 N1 C10 110.78(12) . . ?
C9 N1 C8 110.83(13) . . ?
C9 N1 C10 110.45(13) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C5 C6 C7 177.52(11) . . . . ?
Cl2 C3 C4 C5 -179.38(11) . . . . ?
C1 C2 C3 Cl2 -1.23(18) . . . . ?
C1 C2 C3 C4 179.38(13) . . . . ?
C1 C2 C7 C6 -179.36(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
C3 C4 C5 Cl1 -177.52(11) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
C7 C2 C3 Cl2 178.16(11) . . . . ?
C7 C2 C3 C4 -1.2(2) . . . . ?
O3B C1 C2 C3 96.5(14) . . . . ?
O3B C1 C2 C7 -82.9(14) . . . . ?
O2B C1 C2 C3 -98.1(6) . . . . ?
O2B C1 C2 C7 82.5(6) . . . . ?
O3A C1 C2 C3 85.1(14) . . . . ?
O3A C1 C2 C7 -94.2(14) . . . . ?
O2A C1 C2 C3 -82.2(6) . . . . ?
O2A C1 C2 C7 98.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
