# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_mjh85
_database_code_depnum_ccdc_archive 'CCDC 1020127'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one
_chemical_formula_moiety         'C10 H6 Cl3 N O'
_chemical_formula_sum            'C10 H6 Cl3 N O'
_chemical_formula_weight         262.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H7 Cl2 N O'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   20.5153(14)
_cell_length_b                   6.7406(4)
_cell_length_c                   7.4148(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1025.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5101
_cell_measurement_theta_min      2.9152
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.921
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850   77.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -180.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0259355000
_diffrn_orient_matrix_UB_12      0.0005132000
_diffrn_orient_matrix_UB_13      -0.0631739000
_diffrn_orient_matrix_UB_21      0.0223930000
_diffrn_orient_matrix_UB_22      0.0076181000
_diffrn_orient_matrix_UB_23      -0.0698909000
_diffrn_orient_matrix_UB_31      0.0045961000
_diffrn_orient_matrix_UB_32      -0.0342371000
_diffrn_orient_matrix_UB_33      -0.0165331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1121
_reflns_number_total             1240
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.109
_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)+(0.0268P)²+0.4527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
;
_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 0.19434(2) 0.03543(7) 0.14280(6) 0.02613(15) Uani 1 1 d . . . . .
Cl2 Cl 0.18075(3) 0.2500 -0.18814(7) 0.02060(16) Uani 1 2 d S T P . .
O1 O 0.05058(8) 0.2500 -0.0692(2) 0.0209(4) Uani 1 2 d S T P . .
N1 N 0.04694(10) 0.2500 0.5452(3) 0.0173(4) Uani 1 2 d S T P . .
C1 C -0.01594(11) 0.2500 0.4771(3) 0.0159(5) Uani 1 2 d S T P . .
C2 C -0.07483(12) 0.2500 0.5683(3) 0.0199(5) Uani 1 2 d S T P . .
H2 H -0.0767 0.2500 0.6963 0.024 Uiso 1 2 calc RS T P . .
C3 C -0.13055(12) 0.2500 0.4647(3) 0.0211(5) Uani 1 2 d S T P . .
H3 H -0.1719 0.2500 0.5225 0.025 Uiso 1 2 calc RS T P . .
C4 C -0.12765(11) 0.2500 0.2761(3) 0.0205(5) Uani 1 2 d S T P . .
H4 H -0.1670 0.2500 0.2086 0.025 Uiso 1 2 calc RS T P . .
C5 C -0.06857(11) 0.2500 0.1862(3) 0.0179(5) Uani 1 2 d S T P . .
H5 H -0.0670 0.2500 0.0582 0.022 Uiso 1 2 calc RS T P . .
C6 C -0.01141(11) 0.2500 0.2882(3) 0.0149(5) Uani 1 2 d S T P . .
C7 C 0.05778(10) 0.2500 0.2457(3) 0.0156(5) Uani 1 2 d S T P . .
C8 C 0.08982(11) 0.2500 0.4103(3) 0.0178(5) Uani 1 2 d S T P . .
H8 H 0.1358 0.2500 0.4248 0.021 Uiso 1 2 calc RS T P . .
C9 C 0.08372(10) 0.2500 0.0670(3) 0.0148(5) Uani 1 2 d S T P . .
C10 C 0.15978(11) 0.2500 0.0421(3) 0.0165(5) Uani 1 2 d S T P . .
H1 H 0.0568(14) 0.2500 0.651(4) 0.029(8) Uiso 1 2 d S T 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 C10 1.7754(13) . ?
Cl2 C10 1.761(2) . ?
O1 C9 1.217(3) . ?
N1 C1 1.385(3) . ?
N1 C8 1.332(3) . ?
N1 H1 0.81(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.404(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C7 1.454(3) . ?
C7 C8 1.386(3) . ?
C7 C9 1.428(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.571(3) . ?
C10 Cl1 1.7755(13) 8_565 ?

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
C1 N1 H1 126(2) . . ?
C8 N1 C1 109.97(19) . . ?
C8 N1 H1 124(2) . . ?
N1 C1 C6 107.58(19) . . ?
C2 C1 N1 129.4(2) . . ?
C2 C1 C6 123.0(2) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 H2 121.6 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 106.31(19) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 134.7(2) . . ?
C8 C7 C6 105.78(19) . . ?
C8 C7 C9 129.8(2) . . ?
C9 C7 C6 124.4(2) . . ?
N1 C8 C7 110.4(2) . . ?
N1 C8 H8 124.8 . . ?
C7 C8 H8 124.8 . . ?
O1 C9 C7 124.2(2) . . ?
O1 C9 C10 117.22(19) . . ?
C7 C9 C10 118.62(19) . . ?
Cl1 C10 Cl1 109.10(12) . 8_565 ?
Cl2 C10 Cl1 108.07(9) . . ?
Cl2 C10 Cl1 108.07(9) . 8_565 ?
C9 C10 Cl1 110.33(10) . 8_565 ?
C9 C10 Cl1 110.32(10) . . ?
C9 C10 Cl2 110.88(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl2 0.81(3) 2.81(3) 3.383(2) 130(2) 1_556
N1 H1 O1 0.81(3) 2.08(3) 2.861(2) 162(3) 1_556

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 C9 C10 Cl1 -119.69(10) . . . . ?
O1 C9 C10 Cl1 119.69(10) . . . 8_565 ?
O1 C9 C10 Cl2 0.0 . . . . ?
N1 C1 C2 C3 180.000(0) . . . . ?
N1 C1 C6 C5 180.000(0) . . . . ?
N1 C1 C6 C7 0.000(0) . . . . ?
C1 N1 C8 C7 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C1 C6 C7 C8 0.000(0) . . . . ?
C1 C6 C7 C9 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C5 C6 C7 C8 180.000(0) . . . . ?
C5 C6 C7 C9 0.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
C6 C7 C8 N1 0.000(0) . . . . ?
C6 C7 C9 O1 0.000(0) . . . . ?
C6 C7 C9 C10 180.0 . . . . ?
C7 C9 C10 Cl1 60.31(10) . . . . ?
C7 C9 C10 Cl1 -60.31(10) . . . 8_565 ?
C7 C9 C10 Cl2 180.000(0) . . . . ?
C8 N1 C1 C2 180.000(0) . . . . ?
C8 N1 C1 C6 0.000(0) . . . . ?
C8 C7 C9 O1 180.000(0) . . . . ?
C8 C7 C9 C10 0.000(0) . . . . ?
C9 C7 C8 N1 180.000(0) . . . . ?

_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_mjh88
_database_code_depnum_ccdc_archive 'CCDC 1020128'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2,2-trichloro-1-(1-methyl-1H-indol-3-yl)ethan-1-one '
_chemical_formula_moiety         'C11 H8 Cl3 N O'
_chemical_formula_sum            'C11 H8 Cl3 N O'
_chemical_formula_weight         276.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H8 Cl3 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8736(5)
_cell_length_b                   11.2992(4)
_cell_length_c                   10.6096(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.358(5)
_cell_angle_gamma                90
_cell_volume                     1171.08(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3708
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5575
_cell_measurement_theta_min      3.1856
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9535
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.594
_diffrn_reflns_theta_min         3.192
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00    3.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  -38.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  -38.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600  112.0000   11.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600    0.0000   30.0000 147
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0065681000
_diffrn_orient_matrix_UB_12      -0.0294857000
_diffrn_orient_matrix_UB_13      -0.0596028000
_diffrn_orient_matrix_UB_21      0.0604548000
_diffrn_orient_matrix_UB_22      0.0281131000
_diffrn_orient_matrix_UB_23      -0.0136151000
_diffrn_orient_matrix_UB_31      0.0396741000
_diffrn_orient_matrix_UB_32      -0.0477329000
_diffrn_orient_matrix_UB_33      0.0288213000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2165
_reflns_number_total             2573
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0303
_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)+(0.0277P)²+0.5186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0715
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.07438(5) 0.16419(4) 0.15589(4) 0.02801(12) Uani 1 1 d . . . . .
Cl2 Cl -0.00613(5) 0.35121(4) 0.31666(5) 0.03011(13) Uani 1 1 d . . . . .
Cl3 Cl -0.02966(5) 0.10937(4) 0.38923(5) 0.03406(13) Uani 1 1 d . . . . .
O1 O 0.25315(13) 0.13279(10) 0.46510(11) 0.0293(3) Uani 1 1 d . . . . .
N1 N 0.41174(15) 0.44632(12) 0.25823(13) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.07056(17) 0.20977(14) 0.31627(16) 0.0213(4) Uani 1 1 d . . . . .
C2 C 0.22147(17) 0.21036(14) 0.38699(15) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.31446(17) 0.29921(14) 0.35502(15) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.29744(18) 0.38215(14) 0.25733(15) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.2162 0.3920 0.1982 0.024 Uiso 1 1 calc R . . . .
C5 C 0.45227(17) 0.31605(14) 0.42082(16) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.53117(18) 0.26375(16) 0.52663(16) 0.0272(4) Uani 1 1 d . . . . .
H6 H 0.4956 0.2011 0.5717 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6625(2) 0.30604(19) 0.56363(19) 0.0366(5) Uani 1 1 d . . . . .
H7 H 0.7178 0.2709 0.6345 0.044 Uiso 1 1 calc R . . . .
C8 C 0.7157(2) 0.39881(19) 0.4996(2) 0.0389(5) Uani 1 1 d . . . . .
H8 H 0.8062 0.4257 0.5282 0.047 Uiso 1 1 calc R . . . .
C9 C 0.64040(19) 0.45235(18) 0.39616(19) 0.0328(4) Uani 1 1 d . . . . .
H9 H 0.6764 0.5158 0.3526 0.039 Uiso 1 1 calc R . . . .
C10 C 0.50861(17) 0.40908(15) 0.35815(16) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.4315(2) 0.54210(16) 0.17046(17) 0.0310(4) Uani 1 1 d . . . . .
H11A H 0.3512 0.5477 0.1046 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.5130 0.5260 0.1304 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.4436 0.6169 0.2174 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7834(17) . ?
Cl2 C1 1.7687(17) . ?
Cl3 C1 1.7573(17) . ?
O1 C2 1.2155(19) . ?
N1 C4 1.340(2) . ?
N1 C10 1.386(2) . ?
N1 C11 1.459(2) . ?
C1 C2 1.568(2) . ?
C2 C3 1.434(2) . ?
C3 C4 1.389(2) . ?
C3 C5 1.449(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C10 1.402(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C4 N1 C10 109.15(14) . . ?
C4 N1 C11 125.96(15) . . ?
C10 N1 C11 124.88(15) . . ?
Cl2 C1 Cl1 109.37(9) . . ?
Cl3 C1 Cl1 108.98(9) . . ?
Cl3 C1 Cl2 108.28(9) . . ?
C2 C1 Cl1 107.90(11) . . ?
C2 C1 Cl2 111.87(11) . . ?
C2 C1 Cl3 110.41(11) . . ?
O1 C2 C1 117.11(14) . . ?
O1 C2 C3 123.77(15) . . ?
C3 C2 C1 119.10(13) . . ?
C2 C3 C5 124.52(15) . . ?
C4 C3 C2 129.53(15) . . ?
C4 C3 C5 105.92(14) . . ?
N1 C4 C3 110.44(15) . . ?
N1 C4 H4 124.8 . . ?
C3 C4 H4 124.8 . . ?
C6 C5 C3 134.81(17) . . ?
C6 C5 C10 118.93(16) . . ?
C10 C5 C3 106.24(14) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 118.07(18) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.74(18) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.47(18) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 121.6 . . ?
C8 C9 C10 116.81(19) . . ?
C10 C9 H9 121.6 . . ?
N1 C10 C5 108.25(14) . . ?
N1 C10 C9 128.78(17) . . ?
C9 C10 C5 122.97(17) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C1 C2 O1 -108.10(15) . . . . ?
Cl1 C1 C2 C3 70.60(16) . . . . ?
Cl2 C1 C2 O1 131.56(14) . . . . ?
Cl2 C1 C2 C3 -49.73(18) . . . . ?
Cl3 C1 C2 O1 10.91(18) . . . . ?
Cl3 C1 C2 C3 -170.39(12) . . . . ?
O1 C2 C3 C4 170.56(17) . . . . ?
O1 C2 C3 C5 -7.2(3) . . . . ?
C1 C2 C3 C4 -8.0(3) . . . . ?
C1 C2 C3 C5 174.20(14) . . . . ?
C2 C3 C4 N1 -177.82(16) . . . . ?
C2 C3 C5 C6 -3.0(3) . . . . ?
C2 C3 C5 C10 178.55(15) . . . . ?
C3 C5 C6 C7 -178.97(18) . . . . ?
C3 C5 C10 N1 -0.82(18) . . . . ?
C3 C5 C10 C9 178.84(15) . . . . ?
C4 N1 C10 C5 1.00(18) . . . . ?
C4 N1 C10 C9 -178.63(17) . . . . ?
C4 C3 C5 C6 178.82(18) . . . . ?
C4 C3 C5 C10 0.35(18) . . . . ?
C5 C3 C4 N1 0.26(18) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C5 C10 N1 -179.58(14) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 N1 179.96(17) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C10 N1 C4 C3 -0.78(19) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C11 N1 C4 C3 -179.52(15) . . . . ?
C11 N1 C10 C5 179.76(15) . . . . ?
C11 N1 C10 C9 0.1(3) . . . . ?

_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_mjh91
_database_code_depnum_ccdc_archive 'CCDC 1020129'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
2,2-dichloro-1-(1-methyl-1H-pyrrol-2-yl)ethan-1-one
_chemical_formula_moiety         'C7 H7 Cl2 N O'
_chemical_formula_sum            'C7 H7 Cl2 N O'
_chemical_formula_weight         192.04
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.9311(3)
_cell_length_b                   10.5722(4)
_cell_length_c                   13.4606(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     844.04(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4380
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.6319
_cell_measurement_theta_min      3.0206
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6723
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   47.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3413   77.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600   38.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0600    0.0000    0.0000 146
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0757184000
_diffrn_orient_matrix_UB_12      -0.0184611000
_diffrn_orient_matrix_UB_13      -0.0381066000
_diffrn_orient_matrix_UB_21      -0.0664014000
_diffrn_orient_matrix_UB_22      -0.0544991000
_diffrn_orient_matrix_UB_23      -0.0093608000
_diffrn_orient_matrix_UB_31      -0.0643878000
_diffrn_orient_matrix_UB_32      0.0345028000
_diffrn_orient_matrix_UB_33      -0.0352060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                1836
_reflns_number_total             1892
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.098
_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)+(0.0314P)²+0.1349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0566
_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.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.20035(7) 0.68848(4) 0.16983(3) 0.02281(12) Uani 1 1 d . . . . .
C4 C 0.7675(3) 0.72293(15) 0.32959(13) 0.0158(3) Uani 1 1 d . . . . .
Cl2 Cl 0.63679(9) 0.75443(6) 0.08952(3) 0.03213(15) Uani 1 1 d . . . . .
N1 N 0.9245(3) 0.65876(14) 0.38680(11) 0.0180(3) Uani 1 1 d . . . . .
O1 O 0.5440(3) 0.54949(13) 0.27977(12) 0.0347(4) Uani 1 1 d . . . . .
C1 C 1.0720(3) 0.7427(2) 0.42436(13) 0.0237(4) Uani 1 1 d . . . . .
H1 H 1.1975 0.7224 0.4652 0.028 Uiso 1 1 calc R . . . .
C6 C 0.4696(3) 0.74715(17) 0.19915(12) 0.0167(3) Uani 1 1 d . . . . .
H6 H 0.4547 0.8340 0.2279 0.020 Uiso 1 1 calc R . . . .
C2 C 1.0120(4) 0.86330(19) 0.39409(14) 0.0250(4) Uani 1 1 d . . . . .
H2 H 1.0873 0.9398 0.4105 0.030 Uiso 1 1 calc R . . . .
C7 C 0.9441(4) 0.52131(18) 0.40006(16) 0.0280(5) Uani 1 1 d . . . . .
H7A H 1.0718 0.5027 0.4439 0.042 Uiso 1 1 calc GR . . . .
H7B H 0.9685 0.4811 0.3354 0.042 Uiso 1 1 calc GR . . . .
H7C H 0.8051 0.4885 0.4298 0.042 Uiso 1 1 calc GR . . . .
C5 C 0.5926(3) 0.66133(16) 0.27396(14) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.8203(3) 0.85122(16) 0.33512(13) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.7400 0.9183 0.3042 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.7582(19) . ?
C4 N1 1.385(2) . ?
C4 C5 1.436(3) . ?
C4 C3 1.394(2) . ?
Cl2 C6 1.7794(18) . ?
N1 C1 1.345(2) . ?
N1 C7 1.469(2) . ?
O1 C5 1.220(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C6 H6 1.0000 . ?
C6 C5 1.539(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C3 H3 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 C4 C5 123.59(15) . . ?
N1 C4 C3 107.22(15) . . ?
C3 C4 C5 129.16(16) . . ?
C4 N1 C7 127.25(16) . . ?
C1 N1 C4 108.84(14) . . ?
C1 N1 C7 123.75(17) . . ?
N1 C1 H1 125.4 . . ?
N1 C1 C2 109.25(17) . . ?
C2 C1 H1 125.4 . . ?
Cl1 C6 Cl2 109.59(9) . . ?
Cl1 C6 H6 109.3 . . ?
Cl2 C6 H6 109.3 . . ?
C5 C6 Cl1 111.68(12) . . ?
C5 C6 Cl2 107.69(13) . . ?
C5 C6 H6 109.3 . . ?
C1 C2 H2 126.5 . . ?
C1 C2 C3 107.04(17) . . ?
C3 C2 H2 126.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C5 C6 114.60(14) . . ?
O1 C5 C4 125.27(17) . . ?
O1 C5 C6 120.08(17) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 C4 107.64(16) . . ?
C2 C3 H3 126.2 . . ?

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 C6 C5 C4 -157.34(13) . . . . ?
Cl1 C6 C5 O1 25.2(2) . . . . ?
C4 N1 C1 C2 1.1(2) . . . . ?
Cl2 C6 C5 C4 82.29(17) . . . . ?
Cl2 C6 C5 O1 -95.2(2) . . . . ?
N1 C4 C5 O1 9.5(3) . . . . ?
N1 C4 C5 C6 -167.80(16) . . . . ?
N1 C4 C3 C2 1.2(2) . . . . ?
N1 C1 C2 C3 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C7 N1 C1 C2 176.85(18) . . . . ?
C5 C4 N1 C1 176.45(17) . . . . ?
C5 C4 N1 C7 0.9(3) . . . . ?
C5 C4 C3 C2 -176.54(19) . . . . ?
C3 C4 N1 C1 -1.5(2) . . . . ?
C3 C4 N1 C7 -176.97(18) . . . . ?
C3 C4 C5 O1 -173.0(2) . . . . ?
C3 C4 C5 C6 9.6(3) . . . . ?

_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_mjh92
_database_code_depnum_ccdc_archive 'CCDC 1020130'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2-dichloro-1-(1-methyl-1H-indol-3-yl)ethan-1-one '
_chemical_formula_moiety         'C11 H9 Cl2 N O'
_chemical_formula_sum            'C11 H9 Cl2 N O'
_chemical_formula_weight         242.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H9 Cl2 N O'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9827(4)
_cell_length_b                   11.0753(6)
_cell_length_c                   14.6118(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.091(5)
_cell_angle_gamma                90
_cell_volume                     1054.31(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3367
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.4786
_cell_measurement_theta_min      2.9345
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4305
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.541
_diffrn_reflns_theta_min         3.127
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -77.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega  -79.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038    0.0000   60.0000 174
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0305770000
_diffrn_orient_matrix_UB_12      -0.0111638000
_diffrn_orient_matrix_UB_13      0.0503699000
_diffrn_orient_matrix_UB_21      0.0734492000
_diffrn_orient_matrix_UB_22      0.0441640000
_diffrn_orient_matrix_UB_23      -0.0004912000
_diffrn_orient_matrix_UB_31      -0.0644324000
_diffrn_orient_matrix_UB_32      0.0450408000
_diffrn_orient_matrix_UB_33      0.0129832000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3698
_reflns_number_total             4305
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.057
_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)+(0.0393P)²+0.4651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          
;
Crystal was twinned - processed with hklf5 format data
 with approximately 70:30 ratio of components.
;
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82885(10) 0.49134(6) 0.87623(4) 0.0412(2) Uani 1 1 d . . . . .
Cl2 Cl 0.40880(10) 0.51663(6) 0.86472(5) 0.04156(19) Uani 1 1 d . . . . .
O1 O 0.5334(3) 0.32864(13) 0.72863(12) 0.0408(5) Uani 1 1 d . . . . .
N1 N 0.2331(3) 0.61947(15) 0.49893(13) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.1989(3) 0.50595(19) 0.45511(16) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.0923(3) 0.4767(2) 0.35792(17) 0.0293(5) Uani 1 1 d . . . . .
H2 H 0.0289 0.5369 0.3103 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0826(4) 0.3560(2) 0.33354(18) 0.0367(6) Uani 1 1 d . . . . .
H3 H 0.0109 0.3320 0.2676 0.044 Uiso 1 1 calc R . . . .
C4 C 0.1764(4) 0.2685(2) 0.4042(2) 0.0367(6) Uani 1 1 d . . . . .
H4 H 0.1670 0.1860 0.3852 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2826(4) 0.2987(2) 0.50094(18) 0.0293(5) Uani 1 1 d . . . . .
H5 H 0.3466 0.2383 0.5482 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2936(3) 0.42020(18) 0.52767(15) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.3866(3) 0.48611(17) 0.61814(14) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.3439(3) 0.60729(18) 0.59461(15) 0.0217(4) Uani 1 1 d . . . . .
H8 H 0.3872 0.6722 0.6400 0.026 Uiso 1 1 calc R . . . .
C9 C 0.4990(4) 0.43601(19) 0.71239(16) 0.0262(5) Uani 1 1 d . . . . .
C10 C 0.5759(3) 0.52566(19) 0.79789(16) 0.0269(5) Uani 1 1 d . . . . .
H10 H 0.5719 0.6093 0.7715 0.032 Uiso 1 1 calc R . . . .
C11 C 0.1701(4) 0.7325(2) 0.44583(18) 0.0325(6) Uani 1 1 d . . . . .
H11A H 0.2124 0.8002 0.4919 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.0205 0.7333 0.4131 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.2349 0.7401 0.3967 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.766(2) . ?
Cl2 C10 1.774(2) . ?
O1 C9 1.220(2) . ?
N1 C1 1.392(3) . ?
N1 C8 1.339(3) . ?
N1 C11 1.455(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.400(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C6 C7 1.444(3) . ?
C7 C8 1.391(3) . ?
C7 C9 1.429(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.534(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C1 N1 C11 124.25(18) . . ?
C8 N1 C1 109.17(17) . . ?
C8 N1 C11 126.43(18) . . ?
N1 C1 C6 107.95(18) . . ?
C2 C1 N1 128.6(2) . . ?
C2 C1 C6 123.48(19) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 H2 121.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 106.55(17) . . ?
C5 C6 C1 118.61(19) . . ?
C5 C6 C7 134.8(2) . . ?
C8 C7 C6 106.02(18) . . ?
C8 C7 C9 127.39(19) . . ?
C9 C7 C6 126.59(19) . . ?
N1 C8 C7 110.31(18) . . ?
N1 C8 H8 124.8 . . ?
C7 C8 H8 124.8 . . ?
O1 C9 C7 124.6(2) . . ?
O1 C9 C10 119.1(2) . . ?
C7 C9 C10 116.33(18) . . ?
Cl1 C10 Cl2 109.49(12) . . ?
Cl1 C10 H10 109.4 . . ?
Cl2 C10 H10 109.4 . . ?
C9 C10 Cl1 111.35(15) . . ?
C9 C10 Cl2 107.76(16) . . ?
C9 C10 H10 109.4 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C9 C10 Cl1 43.1(3) . . . . ?
O1 C9 C10 Cl2 -77.0(2) . . . . ?
N1 C1 C2 C3 179.5(2) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
N1 C1 C6 C7 0.3(2) . . . . ?
C1 N1 C8 C7 -0.3(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 C8 -0.5(2) . . . . ?
C1 C6 C7 C9 179.4(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C5 C6 C7 C9 -1.2(4) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C7 C8 N1 0.5(2) . . . . ?
C6 C7 C9 O1 0.8(4) . . . . ?
C6 C7 C9 C10 -177.9(2) . . . . ?
C7 C9 C10 Cl1 -138.08(17) . . . . ?
C7 C9 C10 Cl2 101.8(2) . . . . ?
C8 N1 C1 C2 -179.9(2) . . . . ?
C8 N1 C1 C6 0.0(2) . . . . ?
C8 C7 C9 O1 -179.3(2) . . . . ?
C8 C7 C9 C10 2.0(3) . . . . ?
C9 C7 C8 N1 -179.4(2) . . . . ?
C11 N1 C1 C2 -4.2(4) . . . . ?
C11 N1 C1 C6 175.7(2) . . . . ?
C11 N1 C8 C7 -175.9(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_mjh82
_database_code_depnum_ccdc_archive 'CCDC 1020131'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2-dichloro-3-hydroxy-3-(perfluorophenyl)-1-(p-tolyl)propan-1-one '
_chemical_formula_moiety         'C16 H9 Cl2 F5 O2'
_chemical_formula_sum            'C16 H9 Cl2 F5 O2'
_chemical_formula_weight         399.13
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.3029(5)
_cell_length_b                   20.8740(9)
_cell_length_c                   20.9090(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6242.6(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9619
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5582
_cell_measurement_theta_min      2.9165
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33189
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.620
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -68.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000  120.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0180271000
_diffrn_orient_matrix_UB_12      0.0312928000
_diffrn_orient_matrix_UB_13      0.0046388000
_diffrn_orient_matrix_UB_21      -0.0460363000
_diffrn_orient_matrix_UB_22      -0.0125925000
_diffrn_orient_matrix_UB_23      0.0013717000
_diffrn_orient_matrix_UB_31      0.0043022000
_diffrn_orient_matrix_UB_32      -0.0038174000
_diffrn_orient_matrix_UB_33      0.0335840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5559
_reflns_number_total             7084
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7084
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+4.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1044
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C10(H10), C26(H26)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C19(H19), C20(H20), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_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 0.43943(3) 0.11709(3) 0.49016(2) 0.02747(13) Uani 1 1 d . . . . .
Cl2 Cl 0.59588(3) 0.06686(2) 0.41769(2) 0.02571(12) Uani 1 1 d . . . . .
F1 F 0.59128(8) 0.12641(6) 0.28581(6) 0.0302(3) Uani 1 1 d . . . . .
F2 F 0.47414(10) 0.09977(6) 0.19146(6) 0.0357(3) Uani 1 1 d . . . . .
F3 F 0.29052(10) 0.13002(7) 0.20077(7) 0.0416(3) Uani 1 1 d . . . . .
F4 F 0.22367(8) 0.18494(7) 0.30904(7) 0.0401(3) Uani 1 1 d . . . . .
F5 F 0.34125(8) 0.21591(6) 0.40425(6) 0.0319(3) Uani 1 1 d . . . . .
O1 O 0.62709(11) 0.21773(7) 0.51217(7) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.62217(9) 0.20945(7) 0.38006(7) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.79178(16) -0.00118(12) 0.69927(10) 0.0336(5) Uani 1 1 d . . . . .
H1A H 0.8431 0.0230 0.7188 0.050 Uiso 1 1 calc GR . . . .
H1B H 0.8168 -0.0397 0.6787 0.050 Uiso 1 1 calc GR . . . .
H1C H 0.7467 -0.0136 0.7323 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.74382(14) 0.03990(10) 0.65000(9) 0.0255(4) Uani 1 1 d . . . . .
C3 C 0.77560(14) 0.10124(10) 0.63706(9) 0.0265(4) Uani 1 1 d . . . . .
H3 H 0.8275 0.1177 0.6601 0.032 Uiso 1 1 calc R . . . .
C4 C 0.73312(14) 0.13896(10) 0.59118(9) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.7560 0.1809 0.5831 0.030 Uiso 1 1 calc R . . . .
C5 C 0.65679(14) 0.11570(10) 0.55672(9) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.62409(15) 0.05433(11) 0.56975(10) 0.0292(5) Uani 1 1 d . . . . .
H6 H 0.5721 0.0378 0.5468 0.035 Uiso 1 1 calc R . . . .
C7 C 0.66705(15) 0.01724(11) 0.61602(10) 0.0295(5) Uani 1 1 d . . . . .
H7 H 0.6437 -0.0245 0.6247 0.035 Uiso 1 1 calc R . . . .
C8 C 0.61427(14) 0.16067(10) 0.50990(9) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.54963(13) 0.13647(9) 0.45493(9) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.53477(13) 0.18995(9) 0.40493(9) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.5061 0.2275 0.4272 0.025 Uiso 1 1 calc R . . . .
C11 C 0.47043(14) 0.17089(9) 0.35027(9) 0.0212(4) Uani 1 1 d . . . . .
C12 C 0.50127(14) 0.14172(10) 0.29448(9) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.44140(15) 0.12809(10) 0.24468(10) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.34851(16) 0.14293(10) 0.24918(10) 0.0296(5) Uani 1 1 d . . . . .
C15 C 0.31479(14) 0.17131(10) 0.30389(11) 0.0279(4) Uani 1 1 d . . . . .
C16 C 0.37575(14) 0.18534(10) 0.35299(9) 0.0242(4) Uani 1 1 d . . . . .
Cl3 Cl 0.56730(4) 0.45476(2) 0.28573(2) 0.02912(13) Uani 1 1 d . . . . .
Cl4 Cl 0.49345(3) 0.34655(3) 0.35687(2) 0.02772(13) Uani 1 1 d . . . . .
F6 F 0.56772(9) 0.37456(7) 0.48860(6) 0.0402(3) Uani 1 1 d . . . . .
F7 F 0.55575(10) 0.46675(9) 0.57564(6) 0.0543(5) Uani 1 1 d . . . . .
F8 F 0.64775(12) 0.57975(9) 0.55867(7) 0.0619(5) Uani 1 1 d . . . . .
F9 F 0.74545(11) 0.60051(6) 0.44934(7) 0.0465(4) Uani 1 1 d . . . . .
F10 F 0.75034(9) 0.51133(6) 0.35858(6) 0.0297(3) Uani 1 1 d . . . . .
O3 O 0.71158(10) 0.32416(8) 0.26187(7) 0.0311(3) Uani 1 1 d . . . . .
O4 O 0.69506(11) 0.32951(7) 0.39866(7) 0.0264(3) Uani 1 1 d . . . . .
C17 C 0.39260(17) 0.22326(13) 0.06876(11) 0.0389(6) Uani 1 1 d . . . . .
H17A H 0.3550 0.2567 0.0482 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.3512 0.1909 0.0875 0.058 Uiso 1 1 calc GR . . . .
H17C H 0.4331 0.2030 0.0368 0.058 Uiso 1 1 calc GR . . . .
C18 C 0.45181(15) 0.25271(11) 0.12059(10) 0.0285(5) Uani 1 1 d . . . . .
C19 C 0.41976(15) 0.30465(12) 0.15600(11) 0.0338(5) Uani 1 1 d . . . . .
H19 H 0.3598 0.3221 0.1471 0.041 Uiso 1 1 calc R . . . .
C20 C 0.47356(15) 0.33138(11) 0.20397(11) 0.0324(5) Uani 1 1 d . . . . .
H20 H 0.4500 0.3664 0.2281 0.039 Uiso 1 1 calc R . . . .
C21 C 0.56244(14) 0.30715(10) 0.21707(9) 0.0243(4) Uani 1 1 d . . . . .
C22 C 0.59481(14) 0.25528(10) 0.18171(9) 0.0254(4) Uani 1 1 d . . . . .
H22 H 0.6551 0.2381 0.1901 0.031 Uiso 1 1 calc R . . . .
C23 C 0.53973(15) 0.22842(10) 0.13430(10) 0.0275(4) Uani 1 1 d . . . . .
H23 H 0.5626 0.1928 0.1108 0.033 Uiso 1 1 calc R . . . .
C24 C 0.62862(14) 0.33452(10) 0.26422(10) 0.0230(4) Uani 1 1 d . . . . .
C25 C 0.59469(13) 0.37862(10) 0.31981(9) 0.0220(4) Uani 1 1 d . . . . .
C26 C 0.67422(13) 0.38849(9) 0.36860(9) 0.0212(4) Uani 1 1 d . . . . .
H26 H 0.7310 0.4015 0.3439 0.025 Uiso 1 1 calc R . . . .
C27 C 0.65717(14) 0.43976(10) 0.41851(9) 0.0227(4) Uani 1 1 d . . . . .
C28 C 0.60957(14) 0.43021(11) 0.47570(10) 0.0289(5) Uani 1 1 d . . . . .
C29 C 0.60493(16) 0.47762(14) 0.52193(10) 0.0389(6) Uani 1 1 d . . . . .
C30 C 0.64983(17) 0.53460(13) 0.51329(11) 0.0393(6) Uani 1 1 d . . . . .
C31 C 0.69844(16) 0.54552(11) 0.45770(11) 0.0330(5) Uani 1 1 d . . . . .
C32 C 0.70024(14) 0.49871(10) 0.41155(9) 0.0252(4) Uani 1 1 d . . . . .
H4A H 0.749(2) 0.3204(12) 0.3913(12) 0.034(7) Uiso 1 1 d . . . . .
H2 H 0.634(2) 0.2481(15) 0.3912(13) 0.050(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 C9 1.7861(19) . ?
Cl2 C9 1.776(2) . ?
F1 C12 1.339(2) . ?
F2 C13 1.344(2) . ?
F3 C14 1.336(2) . ?
F4 C15 1.338(2) . ?
F5 C16 1.342(2) . ?
O1 C8 1.206(2) . ?
O2 C10 1.414(2) . ?
O2 H2 0.85(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.506(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.391(3) . ?
C5 C8 1.486(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.559(3) . ?
C9 C10 1.544(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.520(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.367(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.378(3) . ?
Cl3 C25 1.785(2) . ?
Cl4 C25 1.773(2) . ?
F6 C28 1.334(3) . ?
F7 C29 1.344(3) . ?
F8 C30 1.338(3) . ?
F9 C31 1.342(3) . ?
F10 C32 1.345(2) . ?
O3 C24 1.207(2) . ?
O4 C26 1.414(2) . ?
O4 H4A 0.82(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.506(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.395(3) . ?
C21 C22 1.390(3) . ?
C21 C24 1.481(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.560(3) . ?
C25 C26 1.542(3) . ?
C26 H26 1.0000 . ?
C26 C27 1.515(3) . ?
C27 C28 1.390(3) . ?
C27 C32 1.384(3) . ?
C28 C29 1.385(3) . ?
C29 C30 1.364(4) . ?
C30 C31 1.374(4) . ?
C31 C32 1.373(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
C10 O2 H2 110(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.70(19) . . ?
C3 C2 C7 118.27(19) . . ?
C7 C2 C1 121.0(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.20(19) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C8 116.14(18) . . ?
C6 C5 C4 118.85(19) . . ?
C6 C5 C8 124.97(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.22(19) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
O1 C8 C5 122.38(18) . . ?
O1 C8 C9 116.05(18) . . ?
C5 C8 C9 121.56(17) . . ?
Cl2 C9 Cl1 108.91(10) . . ?
C8 C9 Cl1 107.02(13) . . ?
C8 C9 Cl2 111.55(13) . . ?
C10 C9 Cl1 108.76(13) . . ?
C10 C9 Cl2 110.23(13) . . ?
C10 C9 C8 110.27(16) . . ?
O2 C10 C9 109.60(15) . . ?
O2 C10 H10 107.9 . . ?
O2 C10 C11 109.51(15) . . ?
C9 C10 H10 107.9 . . ?
C11 C10 C9 113.77(16) . . ?
C11 C10 H10 107.9 . . ?
C12 C11 C10 123.66(17) . . ?
C12 C11 C16 116.09(18) . . ?
C16 C11 C10 120.18(17) . . ?
F1 C12 C11 121.62(18) . . ?
F1 C12 C13 116.49(17) . . ?
C13 C12 C11 121.88(18) . . ?
F2 C13 C12 119.99(19) . . ?
F2 C13 C14 119.68(19) . . ?
C14 C13 C12 120.33(19) . . ?
F3 C14 C13 120.3(2) . . ?
F3 C14 C15 120.0(2) . . ?
C13 C14 C15 119.70(19) . . ?
F4 C15 C14 119.99(19) . . ?
F4 C15 C16 120.72(19) . . ?
C14 C15 C16 119.29(19) . . ?
F5 C16 C11 119.66(17) . . ?
F5 C16 C15 117.61(18) . . ?
C15 C16 C11 122.70(19) . . ?
C26 O4 H4A 108.6(18) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C19 C18 C17 121.1(2) . . ?
C23 C18 C17 120.6(2) . . ?
C23 C18 C19 118.3(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C24 124.96(19) . . ?
C22 C21 C20 118.76(19) . . ?
C22 C21 C24 116.20(18) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.5 . . ?
O3 C24 C21 122.12(18) . . ?
O3 C24 C25 116.23(18) . . ?
C21 C24 C25 121.65(16) . . ?
Cl4 C25 Cl3 109.34(10) . . ?
C24 C25 Cl3 107.23(13) . . ?
C24 C25 Cl4 110.91(14) . . ?
C26 C25 Cl3 107.88(13) . . ?
C26 C25 Cl4 111.32(13) . . ?
C26 C25 C24 110.02(15) . . ?
O4 C26 C25 109.47(16) . . ?
O4 C26 H26 107.1 . . ?
O4 C26 C27 110.06(16) . . ?
C25 C26 H26 107.1 . . ?
C27 C26 C25 115.57(16) . . ?
C27 C26 H26 107.1 . . ?
C28 C27 C26 124.75(19) . . ?
C32 C27 C26 118.97(17) . . ?
C32 C27 C28 115.84(19) . . ?
F6 C28 C27 121.22(19) . . ?
F6 C28 C29 117.4(2) . . ?
C29 C28 C27 121.4(2) . . ?
F7 C29 C28 119.2(3) . . ?
F7 C29 C30 120.3(2) . . ?
C30 C29 C28 120.5(2) . . ?
F8 C30 C29 120.7(2) . . ?
F8 C30 C31 119.6(3) . . ?
C29 C30 C31 119.7(2) . . ?
F9 C31 C30 120.4(2) . . ?
F9 C31 C32 120.5(2) . . ?
C30 C31 C32 119.1(2) . . ?
F10 C32 C27 119.86(18) . . ?
F10 C32 C31 116.7(2) . . ?
C31 C32 C27 123.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O2 0.82(3) 1.95(3) 2.765(2) 174(3) 2_655
O2 H2 Cl4 0.85(3) 2.96(3) 3.4372(16) 117(2) .
O2 H2 O4 0.85(3) 1.92(3) 2.742(2) 161(3) .

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 C9 C10 O2 175.49(13) . . . . ?
Cl1 C9 C10 C11 -61.54(18) . . . . ?
Cl2 C9 C10 O2 -65.18(17) . . . . ?
Cl2 C9 C10 C11 57.80(18) . . . . ?
F1 C12 C13 F2 1.2(3) . . . . ?
F1 C12 C13 C14 -179.13(18) . . . . ?
F2 C13 C14 F3 -0.7(3) . . . . ?
F2 C13 C14 C15 179.34(18) . . . . ?
F3 C14 C15 F4 1.2(3) . . . . ?
F3 C14 C15 C16 -178.89(19) . . . . ?
F4 C15 C16 F5 -3.3(3) . . . . ?
F4 C15 C16 C11 178.65(19) . . . . ?
O1 C8 C9 Cl1 -104.37(18) . . . . ?
O1 C8 C9 Cl2 136.60(17) . . . . ?
O1 C8 C9 C10 13.8(2) . . . . ?
O2 C10 C11 C12 34.2(3) . . . . ?
O2 C10 C11 C16 -142.55(18) . . . . ?
C1 C2 C3 C4 178.89(19) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C8 178.19(18) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C8 O1 -18.5(3) . . . . ?
C4 C5 C8 C9 161.84(17) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C5 C8 C9 Cl1 75.3(2) . . . . ?
C5 C8 C9 Cl2 -43.7(2) . . . . ?
C5 C8 C9 C10 -166.57(17) . . . . ?
C6 C5 C8 O1 159.0(2) . . . . ?
C6 C5 C8 C9 -20.6(3) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C8 C5 C6 C7 -177.7(2) . . . . ?
C8 C9 C10 O2 58.4(2) . . . . ?
C8 C9 C10 C11 -178.60(15) . . . . ?
C9 C10 C11 C12 -88.9(2) . . . . ?
C9 C10 C11 C16 94.4(2) . . . . ?
C10 C11 C12 F1 2.1(3) . . . . ?
C10 C11 C12 C13 -176.68(19) . . . . ?
C10 C11 C16 F5 -0.4(3) . . . . ?
C10 C11 C16 C15 177.60(19) . . . . ?
C11 C12 C13 F2 -179.97(18) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C11 C16 F5 -177.32(18) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C12 C13 C14 F3 179.65(18) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 F4 -178.84(19) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 F5 176.72(19) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C16 C11 C12 F1 178.93(18) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
Cl3 C25 C26 O4 177.47(13) . . . . ?
Cl3 C25 C26 C27 52.56(19) . . . . ?
Cl4 C25 C26 O4 57.50(18) . . . . ?
Cl4 C25 C26 C27 -67.42(19) . . . . ?
F6 C28 C29 F7 -2.9(3) . . . . ?
F6 C28 C29 C30 176.88(19) . . . . ?
F7 C29 C30 F8 1.8(3) . . . . ?
F7 C29 C30 C31 -178.83(19) . . . . ?
F8 C30 C31 F9 1.5(3) . . . . ?
F8 C30 C31 C32 179.83(19) . . . . ?
F9 C31 C32 F10 -0.4(3) . . . . ?
F9 C31 C32 C27 176.71(18) . . . . ?
O3 C24 C25 Cl3 105.43(19) . . . . ?
O3 C24 C25 Cl4 -135.25(17) . . . . ?
O3 C24 C25 C26 -11.6(2) . . . . ?
O4 C26 C27 C28 -39.1(3) . . . . ?
O4 C26 C27 C32 133.04(18) . . . . ?
C17 C18 C19 C20 179.4(2) . . . . ?
C17 C18 C23 C22 179.8(2) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C18 C23 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C19 C20 C21 C24 175.8(2) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C20 C21 C24 O3 -159.0(2) . . . . ?
C20 C21 C24 C25 20.9(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C21 C24 C25 Cl3 -74.5(2) . . . . ?
C21 C24 C25 Cl4 44.9(2) . . . . ?
C21 C24 C25 C26 168.47(17) . . . . ?
C22 C21 C24 O3 17.8(3) . . . . ?
C22 C21 C24 C25 -162.28(18) . . . . ?
C23 C18 C19 C20 -0.4(3) . . . . ?
C24 C21 C22 C23 -176.83(18) . . . . ?
C24 C25 C26 O4 -65.9(2) . . . . ?
C24 C25 C26 C27 169.22(16) . . . . ?
C25 C26 C27 C28 85.6(2) . . . . ?
C25 C26 C27 C32 -102.3(2) . . . . ?
C26 C27 C28 F6 -5.6(3) . . . . ?
C26 C27 C28 C29 173.31(19) . . . . ?
C26 C27 C32 F10 5.1(3) . . . . ?
C26 C27 C32 C31 -171.93(18) . . . . ?
C27 C28 C29 F7 178.07(18) . . . . ?
C27 C28 C29 C30 -2.1(3) . . . . ?
C28 C27 C32 F10 177.91(17) . . . . ?
C28 C27 C32 C31 0.9(3) . . . . ?
C28 C29 C30 F8 -178.04(19) . . . . ?
C28 C29 C30 C31 1.4(3) . . . . ?
C29 C30 C31 F9 -177.86(19) . . . . ?
C29 C30 C31 C32 0.4(3) . . . . ?
C30 C31 C32 F10 -178.74(18) . . . . ?
C30 C31 C32 C27 -1.6(3) . . . . ?
C32 C27 C28 F6 -177.96(18) . . . . ?
C32 C27 C28 C29 1.0(3) . . . . ?

_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_mjh90
_database_code_depnum_ccdc_archive 'CCDC 1020132'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2-dichloro-3-hydroxy-1-(1H-indol-3-yl)-3-(perfluorophenyl)propan-1-one '
_chemical_formula_moiety         'C17 H8 Cl2 F5 N O2'
_chemical_formula_sum            'C17 H8 Cl2 F5 N O2'
_chemical_formula_weight         424.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H8 Cl2 F2 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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                   7.3186(3)
_cell_length_b                   9.4938(6)
_cell_length_c                   11.7970(7)
_cell_angle_alpha                83.481(5)
_cell_angle_beta                 89.534(4)
_cell_angle_gamma                76.102(4)
_cell_volume                     790.38(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2048
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5561
_cell_measurement_theta_min      2.9709
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6097
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.619
_diffrn_reflns_theta_min         2.977
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega  -85.00   -1.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038    0.0000  150.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0081952000
_diffrn_orient_matrix_UB_12      0.0741835000
_diffrn_orient_matrix_UB_13      -0.0214441000
_diffrn_orient_matrix_UB_21      0.0973788000
_diffrn_orient_matrix_UB_22      -0.0085322000
_diffrn_orient_matrix_UB_23      0.0111350000
_diffrn_orient_matrix_UB_31      0.0205440000
_diffrn_orient_matrix_UB_32      -0.0206631000
_diffrn_orient_matrix_UB_33      -0.0554968000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2690
_reflns_number_total             3273
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.041
_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)+(0.0336P)²+0.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.75040(7) 0.62450(6) 0.36769(5) 0.02423(15) Uani 1 1 d . . . . .
Cl2 Cl 1.07506(7) 0.73297(7) 0.40410(5) 0.02590(15) Uani 1 1 d . . . . .
O1 O 0.8995(2) 0.94359(19) 0.22670(13) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.7874(3) 0.98423(18) 0.50149(14) 0.0323(4) Uani 1 1 d . . . . .
H2 H 0.7404 1.0470 0.4470 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.2765(2) 0.9646(2) 0.20588(16) 0.0219(4) Uani 1 1 d . . . . .
H1 H 0.168(4) 0.946(3) 0.213(2) 0.037(7) Uiso 1 1 d . . . . .
F1 F 1.05809(18) 0.79892(16) 0.64876(12) 0.0322(3) Uani 1 1 d . . . . .
F2 F 1.10618(18) 0.60615(16) 0.83324(11) 0.0321(3) Uani 1 1 d . . . . .
F3 F 0.8455(2) 0.45081(16) 0.89011(12) 0.0356(4) Uani 1 1 d . . . . .
F4 F 0.5269(2) 0.50057(19) 0.76071(13) 0.0445(4) Uani 1 1 d . . . . .
F5 F 0.47417(18) 0.69378(18) 0.57380(12) 0.0386(4) Uani 1 1 d . . . . .
C1 C 0.3237(3) 1.0706(3) 0.12770(18) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.2147(3) 1.1657(3) 0.04280(19) 0.0259(5) Uani 1 1 d . . . . .
H2A H 0.0871 1.1648 0.0295 0.031 Uiso 1 1 calc R . . . .
C3 C 0.2989(3) 1.2611(3) -0.0213(2) 0.0312(6) Uani 1 1 d . . . . .
H3 H 0.2284 1.3281 -0.0802 0.037 Uiso 1 1 calc R . . . .
C4 C 0.4865(3) 1.2618(3) -0.0015(2) 0.0305(6) Uani 1 1 d . . . . .
H4 H 0.5402 1.3307 -0.0463 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5952(3) 1.1650(3) 0.08130(19) 0.0247(5) Uani 1 1 d . . . . .
H5 H 0.7230 1.1661 0.0933 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5150(3) 1.0653(2) 0.14727(17) 0.0182(4) Uani 1 1 d . . . . .
C7 C 0.5808(3) 0.9498(2) 0.23951(17) 0.0179(4) Uani 1 1 d . . . . .
C8 C 0.4261(3) 0.8947(3) 0.27090(18) 0.0202(5) Uani 1 1 d . . . . .
H8 H 0.4267 0.8181 0.3303 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7744(3) 0.8983(2) 0.27633(18) 0.0185(5) Uani 1 1 d . . . . .
C10 C 0.8264(3) 0.7852(2) 0.38514(18) 0.0189(5) Uani 1 1 d . . . . .
C11 C 0.7334(3) 0.8538(2) 0.49110(18) 0.0191(5) Uani 1 1 d . . . . .
H11 H 0.5944 0.8810 0.4758 0.023 Uiso 1 1 calc R . . . .
C12 C 0.7674(3) 0.7502(2) 0.60031(18) 0.0196(5) Uani 1 1 d . . . . .
C13 C 0.9246(3) 0.7258(2) 0.67095(19) 0.0213(5) Uani 1 1 d . . . . .
C14 C 0.9512(3) 0.6268(3) 0.76797(19) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.8186(3) 0.5497(3) 0.79808(19) 0.0244(5) Uani 1 1 d . . . . .
C16 C 0.6580(3) 0.5740(3) 0.7320(2) 0.0256(5) Uani 1 1 d . . . . .
C17 C 0.6350(3) 0.6730(3) 0.63542(19) 0.0242(5) Uani 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 C10 1.778(2) . ?
Cl2 C10 1.776(2) . ?
O1 C9 1.220(2) . ?
O2 H2 0.8400 . ?
O2 C11 1.405(3) . ?
N1 H1 0.85(3) . ?
N1 C1 1.390(3) . ?
N1 C8 1.333(3) . ?
F1 C13 1.336(2) . ?
F2 C14 1.338(2) . ?
F3 C15 1.335(2) . ?
F4 C16 1.336(2) . ?
F5 C17 1.350(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.409(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.370(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.450(3) . ?
C7 C8 1.388(3) . ?
C7 C9 1.436(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.563(3) . ?
C10 C11 1.552(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.513(3) . ?
C12 C13 1.384(3) . ?
C12 C17 1.383(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.371(3) . ?
C15 C16 1.374(3) . ?
C16 C17 1.376(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
C11 O2 H2 109.5 . . ?
C1 N1 H1 126.0(18) . . ?
C8 N1 H1 123.9(18) . . ?
C8 N1 C1 110.12(17) . . ?
N1 C1 C6 107.08(19) . . ?
C2 C1 N1 129.85(19) . . ?
C2 C1 C6 123.1(2) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2A 121.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.62(18) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 135.16(19) . . ?
C8 C7 C6 105.85(18) . . ?
C8 C7 C9 129.9(2) . . ?
C9 C7 C6 123.87(18) . . ?
N1 C8 C7 110.33(19) . . ?
N1 C8 H8 124.8 . . ?
C7 C8 H8 124.8 . . ?
O1 C9 C7 121.7(2) . . ?
O1 C9 C10 118.80(18) . . ?
C7 C9 C10 119.44(17) . . ?
Cl2 C10 Cl1 107.19(12) . . ?
C9 C10 Cl1 110.24(14) . . ?
C9 C10 Cl2 109.32(13) . . ?
C11 C10 Cl1 110.05(14) . . ?
C11 C10 Cl2 110.24(14) . . ?
C11 C10 C9 109.78(18) . . ?
O2 C11 C10 109.77(17) . . ?
O2 C11 H11 106.8 . . ?
O2 C11 C12 112.36(18) . . ?
C10 C11 H11 106.8 . . ?
C12 C11 C10 113.91(18) . . ?
C12 C11 H11 106.8 . . ?
C13 C12 C11 124.60(19) . . ?
C17 C12 C11 119.65(19) . . ?
C17 C12 C13 115.7(2) . . ?
F1 C13 C12 121.25(19) . . ?
F1 C13 C14 116.55(19) . . ?
C14 C13 C12 122.2(2) . . ?
F2 C14 C13 120.04(19) . . ?
F2 C14 C15 119.8(2) . . ?
C15 C14 C13 120.1(2) . . ?
F3 C15 C14 120.5(2) . . ?
F3 C15 C16 120.1(2) . . ?
C14 C15 C16 119.4(2) . . ?
F4 C16 C15 120.1(2) . . ?
F4 C16 C17 120.5(2) . . ?
C15 C16 C17 119.4(2) . . ?
F5 C17 C12 119.8(2) . . ?
F5 C17 C16 117.10(19) . . ?
C16 C17 C12 123.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.85(3) 1.98(3) 2.821(2) 169(3) 1_455

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 C10 C11 O2 -177.39(14) . . . . ?
Cl1 C10 C11 C12 55.6(2) . . . . ?
Cl2 C10 C11 O2 64.6(2) . . . . ?
Cl2 C10 C11 C12 -62.4(2) . . . . ?
O1 C9 C10 Cl1 -123.48(19) . . . . ?
O1 C9 C10 Cl2 -5.9(3) . . . . ?
O1 C9 C10 C11 115.1(2) . . . . ?
O2 C11 C12 C13 -40.4(3) . . . . ?
O2 C11 C12 C17 139.2(2) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
N1 C1 C6 C5 -178.1(2) . . . . ?
N1 C1 C6 C7 0.9(2) . . . . ?
F1 C13 C14 F2 -1.1(3) . . . . ?
F1 C13 C14 C15 178.6(2) . . . . ?
F2 C14 C15 F3 -2.1(3) . . . . ?
F2 C14 C15 C16 178.5(2) . . . . ?
F3 C15 C16 F4 1.1(4) . . . . ?
F3 C15 C16 C17 -178.0(2) . . . . ?
F4 C16 C17 F5 1.3(4) . . . . ?
F4 C16 C17 C12 -178.8(2) . . . . ?
C1 N1 C8 C7 -0.2(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C6 C7 C8 -1.0(2) . . . . ?
C1 C6 C7 C9 172.5(2) . . . . ?
C2 C1 C6 C5 3.0(3) . . . . ?
C2 C1 C6 C7 -178.0(2) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 C8 177.8(2) . . . . ?
C5 C6 C7 C9 -8.7(4) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
C6 C7 C8 N1 0.7(3) . . . . ?
C6 C7 C9 O1 -4.6(3) . . . . ?
C6 C7 C9 C10 173.3(2) . . . . ?
C7 C9 C10 Cl1 58.6(2) . . . . ?
C7 C9 C10 Cl2 176.14(17) . . . . ?
C7 C9 C10 C11 -62.8(2) . . . . ?
C8 N1 C1 C2 178.3(2) . . . . ?
C8 N1 C1 C6 -0.5(3) . . . . ?
C8 C7 C9 O1 167.3(2) . . . . ?
C8 C7 C9 C10 -14.8(3) . . . . ?
C9 C7 C8 N1 -172.3(2) . . . . ?
C9 C10 C11 O2 -55.9(2) . . . . ?
C9 C10 C11 C12 177.13(16) . . . . ?
C10 C11 C12 C13 85.3(3) . . . . ?
C10 C11 C12 C17 -95.1(2) . . . . ?
C11 C12 C13 F1 2.7(3) . . . . ?
C11 C12 C13 C14 -178.0(2) . . . . ?
C11 C12 C17 F5 -1.9(3) . . . . ?
C11 C12 C17 C16 178.2(2) . . . . ?
C12 C13 C14 F2 179.5(2) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C12 C17 F5 177.7(2) . . . . ?
C13 C12 C17 C16 -2.2(3) . . . . ?
C13 C14 C15 F3 178.2(2) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C15 C16 F4 -179.5(2) . . . . ?
C14 C15 C16 C17 1.4(4) . . . . ?
C15 C16 C17 F5 -179.6(2) . . . . ?
C15 C16 C17 C12 0.3(4) . . . . ?
C17 C12 C13 F1 -176.9(2) . . . . ?
C17 C12 C13 C14 2.4(3) . . . . ?

_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_mjh94
_database_code_depnum_ccdc_archive 'CCDC 1020133'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2-dichloro-3-hydroxy-1-(1-methyl-1H-indol-3-yl)-3-(perfluorophenyl)propan-1-one '
_chemical_formula_moiety         'C18 H10 Cl2 F5 N O2'
_chemical_formula_sum            'C18 H10 Cl2 F5 N O2'
_chemical_formula_weight         438.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 F5 Cl2 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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                   7.7970(6)
_cell_length_b                   9.7342(7)
_cell_length_c                   12.0220(10)
_cell_angle_alpha                91.836(7)
_cell_angle_beta                 97.659(6)
_cell_angle_gamma                109.698(7)
_cell_volume                     848.48(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.4574
_cell_measurement_theta_min      2.8023
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7559
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.520
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   75.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   38.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00    9.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -38.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -38.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   63.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257 -120.0000  -45.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0157725000
_diffrn_orient_matrix_UB_12      0.0164396000
_diffrn_orient_matrix_UB_13      0.0591847000
_diffrn_orient_matrix_UB_21      -0.0876902000
_diffrn_orient_matrix_UB_22      -0.0521939000
_diffrn_orient_matrix_UB_23      0.0037409000
_diffrn_orient_matrix_UB_31      0.0402774000
_diffrn_orient_matrix_UB_32      -0.0551066000
_diffrn_orient_matrix_UB_33      0.0071697000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             3605
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.035
_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)+(0.0267P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0945
_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.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41389(9) 0.24919(7) 0.01275(6) 0.02394(18) Uani 1 1 d . . . . .
Cl2 Cl 0.67526(9) 0.13184(7) 0.12467(6) 0.02374(18) Uani 1 1 d . . . . .
O1 O 0.5925(2) 0.4824(2) 0.17541(16) 0.0253(5) Uani 1 1 d . . . . .
O2 O 0.7589(2) 0.47676(19) -0.05875(16) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.6491 0.4633 -0.0863 0.031 Uiso 1 1 calc GR . . . .
N1 N 1.1516(3) 0.4660(3) 0.3287(2) 0.0239(6) Uani 1 1 d . . . . .
F1 F 0.5032(2) 0.27640(18) -0.22619(13) 0.0293(4) Uani 1 1 d . . . . .
F2 F 0.4724(2) 0.07516(18) -0.38793(14) 0.0347(4) Uani 1 1 d . . . . .
F3 F 0.7018(3) -0.08321(18) -0.37187(15) 0.0437(5) Uani 1 1 d . . . . .
F4 F 0.9668(3) -0.0310(2) -0.18964(16) 0.0478(5) Uani 1 1 d . . . . .
F5 F 0.9976(2) 0.17057(19) -0.02309(14) 0.0326(4) Uani 1 1 d . . . . .
C1 C 1.3164(4) 0.4286(3) 0.3599(3) 0.0326(7) Uani 1 1 d . . . . .
H1A H 1.4261 0.5156 0.3599 0.049 Uiso 1 1 calc GR . . . .
H1B H 1.3176 0.3519 0.3056 0.049 Uiso 1 1 calc GR . . . .
H1C H 1.3165 0.3932 0.4353 0.049 Uiso 1 1 calc GR . . . .
C2 C 1.1101(4) 0.5768(3) 0.3827(2) 0.0234(6) Uani 1 1 d . . . . .
C3 C 1.2086(4) 0.6704(3) 0.4770(2) 0.0297(7) Uani 1 1 d . . . . .
H3 H 1.3210 0.6648 0.5146 0.036 Uiso 1 1 calc R . . . .
C4 C 1.1359(4) 0.7713(3) 0.5133(3) 0.0340(8) Uani 1 1 d . . . . .
H4 H 1.1993 0.8371 0.5775 0.041 Uiso 1 1 calc R . . . .
C5 C 0.9707(4) 0.7789(3) 0.4577(3) 0.0317(7) Uani 1 1 d . . . . .
H5 H 0.9250 0.8508 0.4841 0.038 Uiso 1 1 calc R . . . .
C6 C 0.8719(4) 0.6838(3) 0.3649(2) 0.0261(7) Uani 1 1 d . . . . .
H6 H 0.7595 0.6899 0.3278 0.031 Uiso 1 1 calc R . . . .
C7 C 0.9413(4) 0.5786(3) 0.3271(2) 0.0199(6) Uani 1 1 d . . . . .
C8 C 0.8775(4) 0.4606(3) 0.2386(2) 0.0194(6) Uani 1 1 d . . . . .
C9 C 1.0135(4) 0.3977(3) 0.2444(2) 0.0224(6) Uani 1 1 d . . . . .
H9 H 1.0097 0.3176 0.1957 0.027 Uiso 1 1 calc R . . . .
C10 C 0.7019(4) 0.4198(3) 0.1663(2) 0.0179(6) Uani 1 1 d . . . . .
C11 C 0.6499(3) 0.2939(3) 0.0705(2) 0.0174(6) Uani 1 1 d . . . . .
C12 C 0.7728(4) 0.3448(3) -0.0215(2) 0.0176(6) Uani 1 1 d . . . . .
H12 H 0.9025 0.3700 0.0172 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7477(3) 0.2287(3) -0.1156(2) 0.0172(6) Uani 1 1 d . . . . .
C14 C 0.6187(4) 0.2004(3) -0.2117(2) 0.0200(6) Uani 1 1 d . . . . .
C15 C 0.6019(4) 0.0979(3) -0.2972(2) 0.0231(6) Uani 1 1 d . . . . .
C16 C 0.7179(4) 0.0193(3) -0.2894(3) 0.0280(7) Uani 1 1 d . . . . .
C17 C 0.8496(4) 0.0437(3) -0.1967(3) 0.0294(7) Uani 1 1 d . . . . .
C18 C 0.8643(4) 0.1477(3) -0.1119(2) 0.0231(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.777(3) . ?
Cl2 C11 1.787(3) . ?
O1 C10 1.217(3) . ?
O2 H2 0.8400 . ?
O2 C12 1.407(3) . ?
N1 C1 1.456(3) . ?
N1 C2 1.392(3) . ?
N1 C9 1.345(3) . ?
F1 C14 1.343(3) . ?
F2 C15 1.341(3) . ?
F3 C16 1.347(3) . ?
F4 C17 1.343(3) . ?
F5 C18 1.343(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.391(4) . ?
C2 C7 1.401(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(4) . ?
C7 C8 1.447(4) . ?
C8 C9 1.388(4) . ?
C8 C10 1.443(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.564(4) . ?
C11 C12 1.545(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.518(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.388(3) . ?
C14 C15 1.371(4) . ?
C15 C16 1.364(4) . ?
C16 C17 1.366(4) . ?
C17 C18 1.379(4) . ?

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
C12 O2 H2 109.5 . . ?
C2 N1 C1 125.3(2) . . ?
C9 N1 C1 125.7(2) . . ?
C9 N1 C2 109.0(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 107.9(2) . . ?
C3 C2 N1 128.9(3) . . ?
C3 C2 C7 123.2(3) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.5(3) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C8 106.8(2) . . ?
C6 C7 C2 118.6(2) . . ?
C6 C7 C8 134.7(3) . . ?
C9 C8 C7 105.8(2) . . ?
C9 C8 C10 130.2(2) . . ?
C10 C8 C7 124.0(2) . . ?
N1 C9 C8 110.6(2) . . ?
N1 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
O1 C10 C8 122.3(2) . . ?
O1 C10 C11 118.0(2) . . ?
C8 C10 C11 119.7(2) . . ?
Cl1 C11 Cl2 106.98(14) . . ?
C10 C11 Cl1 108.82(16) . . ?
C10 C11 Cl2 111.03(18) . . ?
C12 C11 Cl1 110.23(18) . . ?
C12 C11 Cl2 110.29(16) . . ?
C12 C11 C10 109.4(2) . . ?
O2 C12 C11 109.51(19) . . ?
O2 C12 H12 105.7 . . ?
O2 C12 C13 114.3(2) . . ?
C11 C12 H12 105.7 . . ?
C13 C12 C11 115.1(2) . . ?
C13 C12 H12 105.7 . . ?
C14 C13 C12 124.3(2) . . ?
C14 C13 C18 115.2(2) . . ?
C18 C13 C12 120.5(2) . . ?
F1 C14 C13 120.3(2) . . ?
F1 C14 C15 116.4(2) . . ?
C15 C14 C13 123.3(2) . . ?
F2 C15 C14 120.2(2) . . ?
F2 C15 C16 120.3(2) . . ?
C16 C15 C14 119.5(3) . . ?
F3 C16 C15 120.3(3) . . ?
F3 C16 C17 119.9(2) . . ?
C15 C16 C17 119.7(2) . . ?
F4 C17 C16 120.0(2) . . ?
F4 C17 C18 120.2(3) . . ?
C16 C17 C18 119.7(2) . . ?
F5 C18 C13 119.5(2) . . ?
F5 C18 C17 118.1(2) . . ?
C17 C18 C13 122.5(3) . . ?

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 C11 C12 O2 65.3(2) . . . . ?
Cl1 C11 C12 C13 -65.1(2) . . . . ?
Cl2 C11 C12 O2 -176.76(16) . . . . ?
Cl2 C11 C12 C13 52.8(3) . . . . ?
O1 C10 C11 Cl1 -11.3(3) . . . . ?
O1 C10 C11 Cl2 -128.8(2) . . . . ?
O1 C10 C11 C12 109.3(3) . . . . ?
O2 C12 C13 C14 -40.4(4) . . . . ?
O2 C12 C13 C18 136.1(3) . . . . ?
N1 C2 C3 C4 179.9(3) . . . . ?
N1 C2 C7 C6 -178.7(3) . . . . ?
N1 C2 C7 C8 1.9(3) . . . . ?
F1 C14 C15 F2 -1.7(4) . . . . ?
F1 C14 C15 C16 178.3(3) . . . . ?
F2 C15 C16 F3 -0.9(4) . . . . ?
F2 C15 C16 C17 179.8(3) . . . . ?
F3 C16 C17 F4 2.2(5) . . . . ?
F3 C16 C17 C18 -179.3(3) . . . . ?
F4 C17 C18 F5 -0.2(4) . . . . ?
F4 C17 C18 C13 179.5(3) . . . . ?
C1 N1 C2 C3 -2.2(5) . . . . ?
C1 N1 C2 C7 179.5(2) . . . . ?
C1 N1 C9 C8 179.5(3) . . . . ?
C2 N1 C9 C8 0.6(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C7 C8 C9 -1.6(3) . . . . ?
C2 C7 C8 C10 175.9(3) . . . . ?
C3 C2 C7 C6 2.9(4) . . . . ?
C3 C2 C7 C8 -176.5(3) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C2 -1.7(4) . . . . ?
C5 C6 C7 C8 177.4(3) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C6 C7 C8 C10 -3.4(5) . . . . ?
C7 C2 C3 C4 -2.0(4) . . . . ?
C7 C8 C9 N1 0.7(3) . . . . ?
C7 C8 C10 O1 -0.6(4) . . . . ?
C7 C8 C10 C11 177.8(3) . . . . ?
C8 C10 C11 Cl1 170.3(2) . . . . ?
C8 C10 C11 Cl2 52.8(3) . . . . ?
C8 C10 C11 C12 -69.2(3) . . . . ?
C9 N1 C2 C3 176.7(3) . . . . ?
C9 N1 C2 C7 -1.6(3) . . . . ?
C9 C8 C10 O1 176.2(3) . . . . ?
C9 C8 C10 C11 -5.4(4) . . . . ?
C10 C8 C9 N1 -176.6(3) . . . . ?
C10 C11 C12 O2 -54.3(3) . . . . ?
C10 C11 C12 C13 175.3(2) . . . . ?
C11 C12 C13 C14 87.6(3) . . . . ?
C11 C12 C13 C18 -95.9(3) . . . . ?
C12 C13 C14 F1 -0.9(4) . . . . ?
C12 C13 C14 C15 178.0(3) . . . . ?
C12 C13 C18 F5 1.4(4) . . . . ?
C12 C13 C18 C17 -178.3(3) . . . . ?
C13 C14 C15 F2 179.5(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C13 C18 F5 178.2(2) . . . . ?
C14 C13 C18 C17 -1.5(4) . . . . ?
C14 C15 C16 F3 179.1(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 F4 -178.6(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 F5 -178.8(3) . . . . ?
C16 C17 C18 C13 1.0(5) . . . . ?
C18 C13 C14 F1 -177.5(2) . . . . ?
C18 C13 C14 C15 1.3(4) . . . . ?

_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_mjh86
_database_code_depnum_ccdc_archive 'CCDC 1020134'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2-dichloro-3-hydroxy-3-(4-nitrophenyl)-1-(p-tolyl)propan-1-one '
_chemical_formula_moiety         'C16 H13 Cl2 N O4'
_chemical_formula_sum            'C16 H13 Cl2 N O4'
_chemical_formula_weight         354.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H30 Cl2 O8 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4691(5)
_cell_length_b                   9.8694(6)
_cell_length_c                   10.0248(5)
_cell_angle_alpha                87.037(4)
_cell_angle_beta                 87.379(4)
_cell_angle_gamma                65.674(5)
_cell_volume                     762.23(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5285
_cell_measurement_theta_min      2.9852
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.591
_diffrn_reflns_theta_min         2.991
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1069  119.0000  108.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -77.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   66.0000   23.0000 100

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -38.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
  6 omega  -16.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   38.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  120.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0252932000
_diffrn_orient_matrix_UB_12      -0.0457408000
_diffrn_orient_matrix_UB_13      -0.0384078000
_diffrn_orient_matrix_UB_21      0.0547814000
_diffrn_orient_matrix_UB_22      -0.0636287000
_diffrn_orient_matrix_UB_23      0.0375904000
_diffrn_orient_matrix_UB_31      -0.0693772000
_diffrn_orient_matrix_UB_32      0.0093744000
_diffrn_orient_matrix_UB_33      0.0462069000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2819
_reflns_number_total             3394
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.058
_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)+(0.0572P)²+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1101
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.44731(6) 0.76165(5) 0.85752(5) 0.02920(15) Uani 1 1 d . . . . .
Cl2 Cl 0.39406(6) 0.51489(5) 0.75178(4) 0.02572(14) Uani 1 1 d . . . . .
O1 O 0.70056(18) 0.62067(15) 0.55863(13) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.3732(2) 0.68506(16) 0.48454(13) 0.0307(3) Uani 1 1 d . . . . .
H2 H 0.492(4) 0.650(3) 0.456(3) 0.062(9) Uiso 1 1 d . . . . .
O3 O -0.4693(2) 1.0368(2) 0.66262(19) 0.0493(4) Uani 1 1 d . . . . .
O4 O -0.4131(2) 1.16323(17) 0.80783(16) 0.0408(4) Uani 1 1 d . . . . .
N N -0.3673(2) 1.06847(19) 0.72327(18) 0.0314(4) Uani 1 1 d . . . . .
C1 C 1.2205(3) 0.1685(3) 0.9896(2) 0.0358(5) Uani 1 1 d . . . . .
H1A H 1.2020 0.0770 1.0032 0.054 Uiso 1 1 calc GR . . . .
H1B H 1.2235 0.2084 1.0765 0.054 Uiso 1 1 calc GR . . . .
H1C H 1.3308 0.1466 0.9410 0.054 Uiso 1 1 calc GR . . . .
C2 C 1.0752(3) 0.2811(2) 0.91032(19) 0.0259(4) Uani 1 1 d . . . . .
C3 C 1.1048(2) 0.3291(2) 0.78202(19) 0.0251(4) Uani 1 1 d . . . . .
H3 H 1.2194 0.2931 0.7451 0.030 Uiso 1 1 calc R . . . .
C4 C 0.9692(2) 0.4281(2) 0.70859(19) 0.0253(4) Uani 1 1 d . . . . .
H4 H 0.9919 0.4596 0.6215 0.030 Uiso 1 1 calc R . . . .
C5 C 0.7991(2) 0.4831(2) 0.75933(18) 0.0230(4) Uani 1 1 d . . . . .
C6 C 0.7698(3) 0.4367(2) 0.88885(19) 0.0280(4) Uani 1 1 d . . . . .
H6 H 0.6554 0.4735 0.9263 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9056(3) 0.3384(2) 0.96202(19) 0.0292(4) Uani 1 1 d . . . . .
H7 H 0.8834 0.3086 1.0500 0.035 Uiso 1 1 calc R . . . .
C8 C 0.6634(2) 0.5860(2) 0.66943(18) 0.0231(4) Uani 1 1 d . . . . .
C9 C 0.4678(2) 0.6578(2) 0.71233(18) 0.0222(4) Uani 1 1 d . . . . .
C10 C 0.3577(2) 0.7645(2) 0.60044(18) 0.0233(4) Uani 1 1 d . . . . .
H10 H 0.4036 0.8418 0.5792 0.028 Uiso 1 1 calc R . . . .
C11 C 0.1665(2) 0.8423(2) 0.63620(18) 0.0230(4) Uani 1 1 d . . . . .
C12 C 0.0516(3) 0.7838(2) 0.6001(2) 0.0280(4) Uani 1 1 d . . . . .
H12 H 0.0944 0.6916 0.5567 0.034 Uiso 1 1 calc R . . . .
C13 C -0.1241(3) 0.8580(2) 0.6264(2) 0.0286(4) Uani 1 1 d . . . . .
H13 H -0.2031 0.8192 0.6000 0.034 Uiso 1 1 calc R . . . .
C14 C -0.1820(2) 0.9901(2) 0.69224(18) 0.0251(4) Uani 1 1 d . . . . .
C15 C -0.0718(3) 1.0511(2) 0.7296(2) 0.0277(4) Uani 1 1 d . . . . .
H15 H -0.1149 1.1419 0.7752 0.033 Uiso 1 1 calc R . . . .
C16 C 0.1029(3) 0.9772(2) 0.6993(2) 0.0264(4) Uani 1 1 d . . . . .
H16 H 0.1805 1.0191 0.7220 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.7840(18) . ?
Cl2 C9 1.7841(19) . ?
O1 C8 1.211(2) . ?
O2 H2 0.95(3) . ?
O2 C10 1.406(2) . ?
O3 N 1.227(2) . ?
O4 N 1.223(2) . ?
N C14 1.462(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.501(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.400(3) . ?
C5 C8 1.484(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.558(3) . ?
C9 C10 1.549(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.513(3) . ?
C11 C12 1.389(3) . ?
C11 C16 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 C15 1.375(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 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
C10 O2 H2 105.8(18) . . ?
O3 N C14 118.43(18) . . ?
O4 N O3 123.17(18) . . ?
O4 N C14 118.40(18) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.20(18) . . ?
C7 C2 C1 120.71(18) . . ?
C7 C2 C3 118.07(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.49(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.41(17) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.06(17) . . ?
C4 C5 C8 116.47(16) . . ?
C6 C5 C8 125.47(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.35(18) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.59(18) . . ?
C6 C7 H7 119.2 . . ?
O1 C8 C5 121.05(17) . . ?
O1 C8 C9 116.45(16) . . ?
C5 C8 C9 122.49(16) . . ?
Cl1 C9 Cl2 109.34(10) . . ?
C8 C9 Cl1 107.87(13) . . ?
C8 C9 Cl2 109.43(12) . . ?
C10 C9 Cl1 108.89(12) . . ?
C10 C9 Cl2 110.22(13) . . ?
C10 C9 C8 111.04(15) . . ?
O2 C10 C9 109.84(15) . . ?
O2 C10 H10 108.4 . . ?
O2 C10 C11 107.49(15) . . ?
C9 C10 H10 108.4 . . ?
C11 C10 C9 114.23(15) . . ?
C11 C10 H10 108.4 . . ?
C12 C11 C10 120.42(17) . . ?
C16 C11 C10 120.24(17) . . ?
C16 C11 C12 119.25(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.77(18) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.25(19) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 N 118.90(18) . . ?
C15 C14 N 118.61(18) . . ?
C15 C14 C13 122.48(18) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.39(18) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.81(19) . . ?
C15 C16 H16 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Cl2 0.95(3) 2.61(3) 3.2006(14) 121(2) 2_666
O2 H2 O1 0.95(3) 1.99(3) 2.708(2) 130(2) .

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 C9 C10 O2 179.50(12) . . . . ?
Cl1 C9 C10 C11 -59.64(18) . . . . ?
Cl2 C9 C10 O2 -60.56(17) . . . . ?
Cl2 C9 C10 C11 60.29(18) . . . . ?
O1 C8 C9 Cl1 -119.98(16) . . . . ?
O1 C8 C9 Cl2 121.17(16) . . . . ?
O1 C8 C9 C10 -0.7(2) . . . . ?
O2 C10 C11 C12 27.5(2) . . . . ?
O2 C10 C11 C16 -149.15(17) . . . . ?
O3 N C14 C13 -18.0(3) . . . . ?
O3 N C14 C15 161.93(18) . . . . ?
O4 N C14 C13 162.53(18) . . . . ?
O4 N C14 C15 -17.6(3) . . . . ?
N C14 C15 C16 -179.59(17) . . . . ?
C1 C2 C3 C4 177.47(19) . . . . ?
C1 C2 C7 C6 -177.2(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.42(18) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C8 O1 -0.8(3) . . . . ?
C4 C5 C8 C9 -179.35(16) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C5 C8 C9 Cl1 58.6(2) . . . . ?
C5 C8 C9 Cl2 -60.2(2) . . . . ?
C5 C8 C9 C10 177.89(16) . . . . ?
C6 C5 C8 O1 179.73(19) . . . . ?
C6 C5 C8 C9 1.2(3) . . . . ?
C7 C2 C3 C4 -1.1(3) . . . . ?
C8 C5 C6 C7 178.64(19) . . . . ?
C8 C9 C10 O2 60.9(2) . . . . ?
C8 C9 C10 C11 -178.27(15) . . . . ?
C9 C10 C11 C12 -94.7(2) . . . . ?
C9 C10 C11 C16 88.7(2) . . . . ?
C10 C11 C12 C13 -176.74(17) . . . . ?
C10 C11 C16 C15 178.45(17) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C11 C16 C15 1.8(3) . . . . ?
C12 C13 C14 N -178.77(17) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -1.9(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?

_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_mjh95
_database_code_depnum_ccdc_archive 'CCDC 1020135'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'diethyl 2-(1,1-dichloro-2-(1-methyl-1H-indol-3-yl)-2-oxoethyl)-2-hydroxymalonate '
_chemical_formula_moiety         'C18 H19 Cl2 N O6'
_chemical_formula_sum            'C18 H19 Cl2 N O6'
_chemical_formula_weight         416.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N Cl2 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.6111(5)
_cell_length_b                   10.1757(6)
_cell_length_c                   11.1365(7)
_cell_angle_alpha                87.574(5)
_cell_angle_beta                 70.982(6)
_cell_angle_gamma                75.760(5)
_cell_volume                     893.45(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2555
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5310
_cell_measurement_theta_min      2.8773
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7004
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.594
_diffrn_reflns_theta_min         2.883
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00    0.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -77.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   55.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -94.0000  169.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0126476000
_diffrn_orient_matrix_UB_12      -0.0530388000
_diffrn_orient_matrix_UB_13      -0.0441091000
_diffrn_orient_matrix_UB_21      0.0183211000
_diffrn_orient_matrix_UB_22      -0.0486549000
_diffrn_orient_matrix_UB_23      0.0441348000
_diffrn_orient_matrix_UB_31      -0.0870833000
_diffrn_orient_matrix_UB_32      0.0003218000
_diffrn_orient_matrix_UB_33      0.0255490000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3089
_reflns_number_total             3683
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.070
_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)+(0.0304P)²+0.3719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C15(H15a,H15b,H15c), C18(H18a,H18b,H18c)
;
_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 0.50094(6) 0.50603(5) 0.84032(4) 0.01842(13) Uani 1 1 d . . . . .
Cl2 Cl 0.66226(6) 0.46173(5) 0.56865(4) 0.02086(13) Uani 1 1 d . . . . .
O1 O 0.78599(18) 0.72465(14) 0.68290(14) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.97596(18) 0.42969(16) 0.61137(12) 0.0211(3) Uani 1 1 d . . . . .
O3 O 1.04565(18) 0.54757(14) 0.78678(13) 0.0240(3) Uani 1 1 d . . . . .
O4 O 0.77593(17) 0.59304(13) 0.91891(12) 0.0195(3) Uani 1 1 d . . . . .
O5 O 0.83660(17) 0.22309(13) 0.71801(12) 0.0205(3) Uani 1 1 d . . . . .
O6 O 0.82262(18) 0.31054(13) 0.90388(12) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.2574(2) 0.85777(16) 0.64802(15) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.1036(3) 0.8636(2) 0.6175(2) 0.0246(5) Uani 1 1 d . . . . .
H1A H 0.0669 0.7797 0.6423 0.037 Uiso 1 1 calc GR . . . .
H1B H 0.1263 0.8737 0.5259 0.037 Uiso 1 1 calc GR . . . .
H1C H 0.0140 0.9412 0.6639 0.037 Uiso 1 1 calc GR . . . .
C2 C 0.3233(2) 0.96913(19) 0.65228(17) 0.0158(4) Uani 1 1 d . . . . .
C3 C 0.2541(3) 1.1054(2) 0.63979(18) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.1489 1.1350 0.6245 0.024 Uiso 1 1 calc R . . . .
C4 C 0.3453(3) 1.1957(2) 0.65067(18) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.3020 1.2899 0.6435 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5010(3) 1.1503(2) 0.67214(18) 0.0215(4) Uani 1 1 d . . . . .
H5 H 0.5607 1.2148 0.6799 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5698(3) 1.0148(2) 0.68230(17) 0.0187(4) Uani 1 1 d . . . . .
H6 H 0.6760 0.9857 0.6960 0.022 Uiso 1 1 calc R . . . .
C7 C 0.4801(2) 0.92083(19) 0.67200(17) 0.0154(4) Uani 1 1 d . . . . .
C8 C 0.5078(2) 0.77541(19) 0.67930(17) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.3665(2) 0.7442(2) 0.66455(17) 0.0167(4) Uani 1 1 d . . . . .
H9 H 0.3494 0.6554 0.6659 0.020 Uiso 1 1 calc R . . . .
C10 C 0.6600(2) 0.68595(19) 0.68950(17) 0.0159(4) Uani 1 1 d . . . . .
C11 C 0.6749(2) 0.53186(19) 0.70913(17) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.8469(2) 0.45706(19) 0.72858(17) 0.0159(4) Uani 1 1 d . . . . .
C13 C 0.9007(3) 0.53995(19) 0.81490(17) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.8193(3) 0.6694(2) 1.00651(19) 0.0256(5) Uani 1 1 d . . . . .
H14A H 0.9328 0.6227 1.0105 0.031 Uiso 1 1 calc R . . . .
H14B H 0.7363 0.6721 1.0928 0.031 Uiso 1 1 calc R . . . .
C15 C 0.8197(3) 0.8115(2) 0.9655(2) 0.0306(5) Uani 1 1 d . . . . .
H15A H 0.8289 0.8645 1.0332 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.7141 0.8531 0.9482 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.9163 0.8098 0.8882 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.8331(2) 0.31574(19) 0.78211(17) 0.0161(4) Uani 1 1 d . . . . .
C17 C 0.7986(3) 0.1838(2) 0.96548(19) 0.0230(5) Uani 1 1 d . . . . .
H17A H 0.8174 0.1835 1.0486 0.028 Uiso 1 1 calc R . . . .
H17B H 0.8836 0.1065 0.9122 0.028 Uiso 1 1 calc R . . . .
C18 C 0.6238(3) 0.1660(2) 0.98562(19) 0.0233(5) Uani 1 1 d . . . . .
H18A H 0.6036 0.0918 1.0431 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.6142 0.1443 0.9038 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.5397 0.2501 1.0231 0.035 Uiso 1 1 calc GR . . . .
H2 H 1.025(4) 0.486(3) 0.601(3) 0.063(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7839(18) . ?
Cl2 C11 1.7923(19) . ?
O1 C10 1.222(2) . ?
O2 C12 1.396(2) . ?
O2 H2 0.77(3) . ?
O3 C13 1.205(2) . ?
O4 C13 1.321(2) . ?
O4 C14 1.463(2) . ?
O5 C16 1.195(2) . ?
O6 C16 1.329(2) . ?
O6 C17 1.463(2) . ?
N1 C1 1.459(3) . ?
N1 C2 1.395(2) . ?
N1 C9 1.346(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.389(3) . ?
C2 C7 1.404(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(3) . ?
C7 C8 1.443(3) . ?
C8 C9 1.390(3) . ?
C8 C10 1.436(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.554(3) . ?
C11 C12 1.569(3) . ?
C12 C13 1.550(3) . ?
C12 C16 1.550(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.498(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.504(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C12 O2 H2 108(2) . . ?
C13 O4 C14 116.17(16) . . ?
C16 O6 C17 116.31(15) . . ?
C2 N1 C1 124.80(17) . . ?
C9 N1 C1 125.91(17) . . ?
C9 N1 C2 109.02(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C7 107.79(16) . . ?
C3 C2 N1 128.87(18) . . ?
C3 C2 C7 123.34(18) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 C2 116.86(19) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.92(19) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.77(19) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.67(19) . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C8 106.74(16) . . ?
C6 C7 C2 118.43(18) . . ?
C6 C7 C8 134.82(19) . . ?
C9 C8 C7 106.07(17) . . ?
C9 C8 C10 129.34(17) . . ?
C10 C8 C7 124.41(17) . . ?
N1 C9 C8 110.38(17) . . ?
N1 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
O1 C10 C8 122.90(17) . . ?
O1 C10 C11 115.53(17) . . ?
C8 C10 C11 121.57(16) . . ?
Cl1 C11 Cl2 107.85(10) . . ?
C10 C11 Cl1 110.36(13) . . ?
C10 C11 Cl2 106.84(12) . . ?
C10 C11 C12 112.38(15) . . ?
C12 C11 Cl1 110.23(12) . . ?
C12 C11 Cl2 109.01(12) . . ?
O2 C12 C11 110.12(15) . . ?
O2 C12 C13 108.40(15) . . ?
O2 C12 C16 104.88(15) . . ?
C13 C12 C11 112.92(15) . . ?
C13 C12 C16 111.19(15) . . ?
C16 C12 C11 109.02(15) . . ?
O3 C13 O4 126.17(18) . . ?
O3 C13 C12 120.43(17) . . ?
O4 C13 C12 113.35(16) . . ?
O4 C14 H14A 109.3 . . ?
O4 C14 H14B 109.3 . . ?
O4 C14 C15 111.49(17) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 O6 125.32(18) . . ?
O5 C16 C12 122.55(17) . . ?
O6 C16 C12 112.09(15) . . ?
O6 C17 H17A 109.3 . . ?
O6 C17 H17B 109.3 . . ?
O6 C17 C18 111.80(17) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.77(3) 2.26(3) 2.633(2) 110(3) .

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 C11 C12 O2 156.20(13) . . . . ?
Cl1 C11 C12 C13 -82.47(16) . . . . ?
Cl1 C11 C12 C16 41.64(17) . . . . ?
Cl2 C11 C12 O2 38.00(18) . . . . ?
Cl2 C11 C12 C13 159.34(12) . . . . ?
Cl2 C11 C12 C16 -76.55(15) . . . . ?
O1 C10 C11 Cl1 128.45(15) . . . . ?
O1 C10 C11 Cl2 -114.55(16) . . . . ?
O1 C10 C11 C12 5.0(2) . . . . ?
O2 C12 C13 O3 -14.3(2) . . . . ?
O2 C12 C13 O4 168.02(15) . . . . ?
O2 C12 C16 O5 -43.4(2) . . . . ?
O2 C12 C16 O6 134.68(16) . . . . ?
N1 C2 C3 C4 178.64(18) . . . . ?
N1 C2 C7 C6 -178.74(15) . . . . ?
N1 C2 C7 C8 0.15(19) . . . . ?
C1 N1 C2 C3 5.7(3) . . . . ?
C1 N1 C2 C7 -174.12(16) . . . . ?
C1 N1 C9 C8 173.78(17) . . . . ?
C2 N1 C9 C8 -0.4(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C7 C8 C9 -0.39(19) . . . . ?
C2 C7 C8 C10 175.15(17) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C3 C2 C7 C8 -179.71(17) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 C8 -178.78(19) . . . . ?
C6 C7 C8 C9 178.2(2) . . . . ?
C6 C7 C8 C10 -6.2(3) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C7 C8 C9 N1 0.5(2) . . . . ?
C7 C8 C10 O1 -5.9(3) . . . . ?
C7 C8 C10 C11 174.42(16) . . . . ?
C8 C10 C11 Cl1 -51.9(2) . . . . ?
C8 C10 C11 Cl2 65.13(19) . . . . ?
C8 C10 C11 C12 -175.35(15) . . . . ?
C9 N1 C2 C3 -179.98(18) . . . . ?
C9 N1 C2 C7 0.2(2) . . . . ?
C9 C8 C10 O1 168.53(18) . . . . ?
C9 C8 C10 C11 -11.1(3) . . . . ?
C10 C8 C9 N1 -174.73(18) . . . . ?
C10 C11 C12 O2 -80.24(18) . . . . ?
C10 C11 C12 C13 41.1(2) . . . . ?
C10 C11 C12 C16 165.20(14) . . . . ?
C11 C12 C13 O3 -136.62(18) . . . . ?
C11 C12 C13 O4 45.7(2) . . . . ?
C11 C12 C16 O5 74.5(2) . . . . ?
C11 C12 C16 O6 -107.41(17) . . . . ?
C13 O4 C14 C15 81.9(2) . . . . ?
C13 C12 C16 O5 -160.34(18) . . . . ?
C13 C12 C16 O6 17.7(2) . . . . ?
C14 O4 C13 O3 0.8(3) . . . . ?
C14 O4 C13 C12 178.31(16) . . . . ?
C16 O6 C17 C18 -71.1(2) . . . . ?
C16 C12 C13 O3 100.5(2) . . . . ?
C16 C12 C13 O4 -77.2(2) . . . . ?
C17 O6 C16 O5 -5.6(3) . . . . ?
C17 O6 C16 C12 176.38(15) . . . . ?

_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_mjh87
_database_code_depnum_ccdc_archive 'CCDC 1020136'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'(1R*,3R*)-2,2-dichloro-3-hydroxy-3-(4-nitrophenyl)-1-(p-tolyl)propyl 4-nitrobenzoate '
_chemical_formula_moiety         'C23 H18 Cl2 N2 O7'
_chemical_formula_sum            'C23 H18 Cl2 N2 O7'
_chemical_formula_weight         505.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H10 O4 N Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4445(4)
_cell_length_b                   15.4187(7)
_cell_length_c                   17.2259(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2242.87(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3883
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.6435
_cell_measurement_theta_min      2.8889
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10321
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.707
_diffrn_reflns_theta_min         2.895
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00    8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00  -15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  140.0000   98.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   26.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000  -60.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0294677000
_diffrn_orient_matrix_UB_12      0.0425921000
_diffrn_orient_matrix_UB_13      0.0058159000
_diffrn_orient_matrix_UB_21      -0.0785622000
_diffrn_orient_matrix_UB_22      -0.0156584000
_diffrn_orient_matrix_UB_23      -0.0038325000
_diffrn_orient_matrix_UB_31      -0.0032572000
_diffrn_orient_matrix_UB_32      -0.0075954000
_diffrn_orient_matrix_UB_33      0.0405883000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                4154
_reflns_number_total             4711
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0400
_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)+(0.0342P)²+0.5820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0879
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.44620(10) 0.25979(5) 0.86675(5) 0.0309(2) Uani 1 1 d . . . . .
Cl2 Cl 0.68698(10) 0.31677(5) 0.97420(4) 0.0291(2) Uani 1 1 d . . . . .
N1 N 1.0539(4) 0.02445(18) 0.76494(16) 0.0299(6) Uani 1 1 d . . . . .
N2 N 1.1501(4) 0.7902(2) 0.91171(18) 0.0428(8) Uani 1 1 d . . . . .
O1 O 0.9844(3) -0.03590(16) 0.73374(16) 0.0423(7) Uani 1 1 d . . . . .
O2 O 1.1933(3) 0.02127(17) 0.78370(15) 0.0400(6) Uani 1 1 d . . . . .
O3 O 0.6356(3) 0.36323(14) 0.75054(13) 0.0289(5) Uani 1 1 d . . . . .
H3 H 0.6903 0.3986 0.7249 0.043 Uiso 1 1 calc GR . . . .
O4 O 0.6372(3) 0.49040(13) 0.89870(13) 0.0243(5) Uani 1 1 d . . . . .
O5 O 0.4988(3) 0.59162(16) 0.83585(17) 0.0472(7) Uani 1 1 d . . . . .
O6 O 1.1383(4) 0.86577(18) 0.89129(19) 0.0566(8) Uani 1 1 d . . . . .
O7 O 1.2712(4) 0.7577(2) 0.93708(19) 0.0595(9) Uani 1 1 d . . . . .
C1 C 0.9670(4) 0.1044(2) 0.78021(18) 0.0250(7) Uani 1 1 d . . . . .
C2 C 0.8232(4) 0.1162(2) 0.74421(18) 0.0251(7) Uani 1 1 d . . . . .
H2 H 0.7805 0.0730 0.7109 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7428(4) 0.1927(2) 0.75781(18) 0.0238(7) Uani 1 1 d . . . . .
H3A H 0.6448 0.2029 0.7323 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8030(4) 0.2550(2) 0.80824(17) 0.0219(6) Uani 1 1 d . . . . .
C5 C 0.9474(4) 0.2397(2) 0.84431(18) 0.0263(7) Uani 1 1 d . . . . .
H5 H 0.9889 0.2817 0.8792 0.032 Uiso 1 1 calc R . . . .
C6 C 1.0318(4) 0.1647(2) 0.83052(18) 0.0267(7) Uani 1 1 d . . . . .
H6 H 1.1312 0.1547 0.8548 0.032 Uiso 1 1 calc R . . . .
C7 C 0.7178(4) 0.3400(2) 0.81931(18) 0.0235(7) Uani 1 1 d . . . . .
H7 H 0.7981 0.3859 0.8308 0.028 Uiso 1 1 calc R . . . .
C8 C 0.5917(4) 0.3409(2) 0.88442(17) 0.0222(7) Uani 1 1 d . . . . .
C9 C 0.5091(4) 0.4299(2) 0.88811(18) 0.0231(7) Uani 1 1 d . . . . .
H9 H 0.4599 0.4415 0.8363 0.028 Uiso 1 1 calc R . . . .
C10 C 0.3843(4) 0.4424(2) 0.94922(18) 0.0248(7) Uani 1 1 d . . . . .
C11 C 0.2297(4) 0.4161(2) 0.9348(2) 0.0295(8) Uani 1 1 d . . . . .
H11 H 0.2043 0.3901 0.8863 0.035 Uiso 1 1 calc R . . . .
C12 C 0.1128(4) 0.4271(2) 0.9896(2) 0.0342(8) Uani 1 1 d . . . . .
H12 H 0.0094 0.4055 0.9796 0.041 Uiso 1 1 calc R . . . .
C13 C 0.1435(5) 0.4691(2) 1.0591(2) 0.0340(9) Uani 1 1 d . . . . .
C14 C 0.2963(5) 0.4973(2) 1.07237(19) 0.0340(8) Uani 1 1 d . . . . .
H14 H 0.3194 0.5271 1.1193 0.041 Uiso 1 1 calc R . . . .
C15 C 0.4166(4) 0.4835(2) 1.0194(2) 0.0296(8) Uani 1 1 d . . . . .
H15 H 0.5213 0.5021 1.0308 0.036 Uiso 1 1 calc R . . . .
C16 C 0.0153(5) 0.4853(3) 1.1176(2) 0.0466(10) Uani 1 1 d . . . . .
H16A H -0.0849 0.4615 1.0984 0.070 Uiso 1 1 calc GR . . . .
H16B H 0.0037 0.5479 1.1259 0.070 Uiso 1 1 calc GR . . . .
H16C H 0.0431 0.4572 1.1668 0.070 Uiso 1 1 calc GR . . . .
C17 C 0.6156(4) 0.5708(2) 0.8695(2) 0.0285(7) Uani 1 1 d . . . . .
C18 C 0.7543(4) 0.6276(2) 0.88332(19) 0.0285(8) Uani 1 1 d . . . . .
C19 C 0.7545(5) 0.7104(2) 0.8511(2) 0.0384(9) Uani 1 1 d . . . . .
H19 H 0.6653 0.7300 0.8224 0.046 Uiso 1 1 calc R . . . .
C20 C 0.8828(5) 0.7639(2) 0.8606(2) 0.0400(9) Uani 1 1 d . . . . .
H20 H 0.8834 0.8205 0.8388 0.048 Uiso 1 1 calc R . . . .
C21 C 1.0104(4) 0.7339(2) 0.9022(2) 0.0329(8) Uani 1 1 d . . . . .
C22 C 1.0141(5) 0.6526(2) 0.9353(2) 0.0352(8) Uani 1 1 d . . . . .
H22 H 1.1036 0.6337 0.9641 0.042 Uiso 1 1 calc R . . . .
C23 C 0.8845(4) 0.5995(2) 0.9255(2) 0.0322(8) Uani 1 1 d . . . . .
H23 H 0.8842 0.5432 0.9479 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.779(3) . ?
Cl2 C8 1.782(3) . ?
N1 O1 1.224(4) . ?
N1 O2 1.222(4) . ?
N1 C1 1.458(4) . ?
N2 O6 1.222(4) . ?
N2 O7 1.220(5) . ?
N2 C21 1.473(5) . ?
O3 H3 0.8400 . ?
O3 C7 1.419(4) . ?
O4 C9 1.439(4) . ?
O4 C17 1.351(4) . ?
O5 C17 1.188(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.384(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.391(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.507(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(5) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.547(4) . ?
C8 C9 1.541(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.502(5) . ?
C10 C11 1.389(5) . ?
C10 C15 1.392(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(5) . ?
C13 C14 1.380(6) . ?
C13 C16 1.500(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.481(5) . ?
C18 C19 1.393(5) . ?
C18 C23 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.371(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(5) . ?
C21 C22 1.378(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(5) . ?
C23 H23 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
O1 N1 C1 118.7(3) . . ?
O2 N1 O1 123.2(3) . . ?
O2 N1 C1 118.1(3) . . ?
O6 N2 C21 117.7(4) . . ?
O7 N2 O6 124.3(4) . . ?
O7 N2 C21 118.0(3) . . ?
C7 O3 H3 109.5 . . ?
C17 O4 C9 116.5(2) . . ?
C2 C1 N1 118.3(3) . . ?
C2 C1 C6 122.8(3) . . ?
C6 C1 N1 118.8(3) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.1(3) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3A 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 120.7(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 H6 121.1 . . ?
O3 C7 C4 110.3(2) . . ?
O3 C7 H7 108.5 . . ?
O3 C7 C8 105.4(2) . . ?
C4 C7 H7 108.5 . . ?
C4 C7 C8 115.3(2) . . ?
C8 C7 H7 108.5 . . ?
Cl1 C8 Cl2 108.26(16) . . ?
C7 C8 Cl1 110.2(2) . . ?
C7 C8 Cl2 108.4(2) . . ?
C9 C8 Cl1 108.7(2) . . ?
C9 C8 Cl2 110.8(2) . . ?
C9 C8 C7 110.5(2) . . ?
O4 C9 C8 104.0(2) . . ?
O4 C9 H9 108.1 . . ?
O4 C9 C10 110.9(2) . . ?
C8 C9 H9 108.1 . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 H9 108.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 C15 118.2(3) . . ?
C15 C10 C9 121.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C16 121.5(4) . . ?
C14 C13 C12 117.7(3) . . ?
C14 C13 C16 120.8(4) . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C18 112.1(3) . . ?
O5 C17 O4 122.8(3) . . ?
O5 C17 C18 125.1(3) . . ?
C19 C18 C17 118.6(3) . . ?
C23 C18 C17 121.8(3) . . ?
C23 C18 C19 119.6(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.6(3) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 N2 119.2(3) . . ?
C20 C21 C22 122.7(3) . . ?
C22 C21 N2 118.1(4) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 C21 118.1(4) . . ?
C23 C22 H22 120.9 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(3) . . ?
C22 C23 H23 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 2.14 2.894(3) 149.8 3_756
O3 H3 O6 0.84 2.52 3.101(4) 127.1 3_746

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 C8 C9 O4 -177.32(19) . . . . ?
Cl1 C8 C9 C10 59.8(3) . . . . ?
Cl2 C8 C9 O4 63.9(3) . . . . ?
Cl2 C8 C9 C10 -59.0(3) . . . . ?
N1 C1 C2 C3 -178.9(3) . . . . ?
N1 C1 C6 C5 -179.8(3) . . . . ?
N2 C21 C22 C23 -179.1(3) . . . . ?
O1 N1 C1 C2 -14.2(4) . . . . ?
O1 N1 C1 C6 165.4(3) . . . . ?
O2 N1 C1 C2 165.5(3) . . . . ?
O2 N1 C1 C6 -15.0(4) . . . . ?
O3 C7 C8 Cl1 64.1(3) . . . . ?
O3 C7 C8 Cl2 -177.6(2) . . . . ?
O3 C7 C8 C9 -56.0(3) . . . . ?
O4 C9 C10 C11 156.0(3) . . . . ?
O4 C9 C10 C15 -20.9(4) . . . . ?
O4 C17 C18 C19 175.0(3) . . . . ?
O4 C17 C18 C23 -3.3(5) . . . . ?
O5 C17 C18 C19 -4.0(5) . . . . ?
O5 C17 C18 C23 177.7(4) . . . . ?
O6 N2 C21 C20 9.9(5) . . . . ?
O6 N2 C21 C22 -170.5(3) . . . . ?
O7 N2 C21 C20 -167.8(3) . . . . ?
O7 N2 C21 C22 11.8(5) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C2 C3 C4 C7 176.9(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C7 O3 -29.9(4) . . . . ?
C3 C4 C7 C8 89.3(3) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C7 C8 Cl1 -57.9(3) . . . . ?
C4 C7 C8 Cl2 60.5(3) . . . . ?
C4 C7 C8 C9 -178.0(3) . . . . ?
C5 C4 C7 O3 146.0(3) . . . . ?
C5 C4 C7 C8 -94.7(3) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
C7 C4 C5 C6 -175.5(3) . . . . ?
C7 C8 C9 O4 -56.3(3) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C8 C9 C10 C11 -84.7(4) . . . . ?
C8 C9 C10 C15 98.4(4) . . . . ?
C9 O4 C17 O5 -0.8(5) . . . . ?
C9 O4 C17 C18 -179.8(3) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C9 C10 C15 C14 176.8(3) . . . . ?
C10 C11 C12 C13 3.7(5) . . . . ?
C11 C10 C15 C14 -0.1(5) . . . . ?
C11 C12 C13 C14 -1.8(5) . . . . ?
C11 C12 C13 C16 177.0(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C10 1.9(5) . . . . ?
C15 C10 C11 C12 -2.7(5) . . . . ?
C16 C13 C14 C15 -179.8(3) . . . . ?
C17 O4 C9 C8 150.4(3) . . . . ?
C17 O4 C9 C10 -82.5(3) . . . . ?
C17 C18 C19 C20 -178.0(3) . . . . ?
C17 C18 C23 C22 177.8(3) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C19 C18 C23 C22 -0.5(5) . . . . ?
C19 C20 C21 N2 179.0(3) . . . . ?
C19 C20 C21 C22 -0.6(6) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C23 C18 C19 C20 0.4(5) . . . . ?

_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_mjh83
_database_code_depnum_ccdc_archive 'CCDC 1020137'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'(1R*,3R*)-1-(4-(tert-butyl)phenyl)-2,2-dichloro-3-hydroxy-3-(4-nitrophenyl)propyl 4-nitrobenzoate '
_chemical_formula_moiety         'C26 H23 Cl2 N2 O7, C H Cl3'
_chemical_formula_sum            'C27 H24 Cl5 N2 O7'
_chemical_formula_weight         665.73
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 Cl2 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.7051(3)
_cell_length_b                   14.1443(6)
_cell_length_c                   15.7774(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.326(4)
_cell_angle_gamma                90
_cell_volume                     1467.17(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5996
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5909
_cell_measurement_theta_min      2.9955
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9761
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.648
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.654
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   17.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   89.0000  -39.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   89.0000  140.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00    7.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819  112.0000  -16.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   37.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819  -77.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   65.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819   38.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819   77.0000  120.0000 38
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0206592000
_diffrn_orient_matrix_UB_12      0.0259916000
_diffrn_orient_matrix_UB_13      0.0357597000
_diffrn_orient_matrix_UB_21      -0.0853261000
_diffrn_orient_matrix_UB_22      0.0211351000
_diffrn_orient_matrix_UB_23      -0.0270671000
_diffrn_orient_matrix_UB_31      -0.0626758000
_diffrn_orient_matrix_UB_32      -0.0373364000
_diffrn_orient_matrix_UB_33      0.0095224000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.587
_reflns_Friedel_fraction_max     0.453
_reflns_number_gt                4726
_reflns_number_total             4882
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     311
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0374
_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)+(0.0430P)²+1.3735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          
;
Libration in the NO2 group can be modelled with an
 addtiional minor position, but this adds no further
 chemical information to the model and has
 therefore not been employed in the final
 refinement.
;
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C27(H27)
3.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.78730(13) 0.80620(6) 0.57581(6) 0.0262(2) Uani 1 1 d . . . . .
Cl2 Cl 0.36290(12) 0.79970(6) 0.49409(6) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.3821(12) 0.4954(3) 0.8051(3) 0.0750(17) Uani 1 1 d . . . . .
N2 N -0.0553(4) 0.6092(2) -0.01091(18) 0.0193(6) Uani 1 1 d . . . . .
O1 O 0.5154(11) 0.4677(4) 0.8625(3) 0.117(2) Uani 1 1 d . . . . .
O2 O 0.1966(10) 0.4875(3) 0.8049(4) 0.0998(19) Uani 1 1 d . . . . .
O4 O 0.5221(3) 0.73821(17) 0.33865(14) 0.0165(5) Uani 1 1 d . . . . .
O5 O 0.7596(4) 0.7181(2) 0.25828(18) 0.0310(7) Uani 1 1 d . . . . .
O6 O -0.2284(4) 0.6330(2) -0.00800(18) 0.0317(7) Uani 1 1 d . . . . .
O7 O -0.0089(4) 0.5647(2) -0.07049(16) 0.0273(6) Uani 1 1 d . . . . .
C1 C 0.9368(9) 1.2279(3) 0.3745(3) 0.0508(14) Uani 1 1 d . . . . .
H1A H 0.9489 1.2934 0.3558 0.076 Uiso 1 1 calc R . . . .
H1B H 0.9124 1.2273 0.4337 0.076 Uiso 1 1 calc R . . . .
H1C H 1.0630 1.1937 0.3725 0.076 Uiso 1 1 calc R . . . .
C2 C 0.5663(8) 1.2376(3) 0.3148(4) 0.0470(12) Uani 1 1 d . . . . .
H2A H 0.5872 1.3027 0.2970 0.070 Uiso 1 1 calc R . . . .
H2B H 0.4515 1.2096 0.2745 0.070 Uiso 1 1 calc R . . . .
H2C H 0.5370 1.2378 0.3732 0.070 Uiso 1 1 calc R . . . .
C3 C 0.7990(9) 1.1803(3) 0.2217(3) 0.0440(12) Uani 1 1 d . . . . .
H3A H 0.8143 1.2457 0.2035 0.066 Uiso 1 1 calc R . . . .
H3B H 0.9240 1.1451 0.2201 0.066 Uiso 1 1 calc R . . . .
H3C H 0.6846 1.1506 0.1825 0.066 Uiso 1 1 calc R . . . .
C4 C 0.7583(6) 1.1797(3) 0.3140(3) 0.0284(8) Uani 1 1 d . . . . .
C5 C 0.7349(6) 1.0772(3) 0.3412(2) 0.0232(7) Uani 1 1 d . . . . .
C6 C 0.8992(6) 1.0238(3) 0.3799(3) 0.0296(9) Uani 1 1 d . . . . .
H6 H 1.0302 1.0520 0.3919 0.035 Uiso 1 1 calc R . . . .
C7 C 0.8788(6) 0.9295(3) 0.4018(3) 0.0266(8) Uani 1 1 d . . . . .
H7 H 0.9957 0.8946 0.4282 0.032 Uiso 1 1 calc R . . . .
C8 C 0.6897(5) 0.8857(2) 0.3857(2) 0.0190(7) Uani 1 1 d . . . . .
C9 C 0.5237(6) 0.9388(3) 0.3461(3) 0.0294(9) Uani 1 1 d . . . . .
H9 H 0.3925 0.9107 0.3339 0.035 Uiso 1 1 calc R . . . .
C10 C 0.5471(6) 1.0319(3) 0.3245(3) 0.0338(10) Uani 1 1 d . . . . .
H10 H 0.4306 1.0664 0.2971 0.041 Uiso 1 1 calc R . . . .
C11 C 0.6733(5) 0.7820(2) 0.4051(2) 0.0166(7) Uani 1 1 d . . . . .
H11 H 0.8076 0.7517 0.4041 0.020 Uiso 1 1 calc R . . . .
C12 C 0.6094(5) 0.7542(2) 0.4899(2) 0.0170(7) Uani 1 1 d . . . . .
C13 C 0.6064(5) 0.6454(2) 0.5004(2) 0.0179(7) Uani 1 1 d . . . . .
H13 H 0.5084 0.6184 0.4502 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5463(5) 0.6117(2) 0.5826(2) 0.0180(7) Uani 1 1 d . . . . .
C15 C 0.6916(6) 0.5982(3) 0.6577(2) 0.0250(8) Uani 1 1 d . . . . .
H15 H 0.8292 0.6149 0.6585 0.030 Uiso 1 1 calc R . . . .
C16 C 0.6390(8) 0.5611(3) 0.7308(3) 0.0372(10) Uani 1 1 d . . . . .
H16 H 0.7386 0.5517 0.7819 0.045 Uiso 1 1 calc R . . . .
C17 C 0.4396(8) 0.5381(3) 0.7281(3) 0.0387(10) Uani 1 1 d . . . . .
C18 C 0.2904(7) 0.5516(3) 0.6562(3) 0.0373(10) Uani 1 1 d . . . . .
H18 H 0.1528 0.5361 0.6567 0.045 Uiso 1 1 calc R . . . .
C19 C 0.3457(6) 0.5883(3) 0.5831(3) 0.0264(8) Uani 1 1 d . . . . .
H19 H 0.2449 0.5976 0.5323 0.032 Uiso 1 1 calc R . . . .
C20 C 0.5848(5) 0.7140(2) 0.2658(2) 0.0192(7) Uani 1 1 d . . . . .
C21 C 0.4145(5) 0.6844(3) 0.1965(2) 0.0185(7) Uani 1 1 d . . . . .
C22 C 0.2130(5) 0.6943(2) 0.2050(2) 0.0180(7) Uani 1 1 d . . . . .
H22 H 0.1817 0.7170 0.2576 0.022 Uiso 1 1 calc R . . . .
C23 C 0.0573(5) 0.6707(3) 0.1360(2) 0.0191(7) Uani 1 1 d . . . . .
H23 H -0.0813 0.6783 0.1401 0.023 Uiso 1 1 calc R . . . .
C24 C 0.1092(5) 0.6359(2) 0.0618(2) 0.0172(7) Uani 1 1 d . . . . .
C25 C 0.3075(5) 0.6242(3) 0.0519(2) 0.0222(7) Uani 1 1 d . . . . .
H25 H 0.3383 0.5994 0.0000 0.027 Uiso 1 1 calc R . . . .
C26 C 0.4594(5) 0.6499(3) 0.1204(2) 0.0230(8) Uani 1 1 d . . . . .
H26 H 0.5975 0.6437 0.1151 0.028 Uiso 1 1 calc R . . . .
Cl3 Cl 0.8031(3) 1.08710(12) 0.59194(12) 0.0710(4) Uani 1 1 d . . . . .
Cl4 Cl 0.5001(2) 1.05789(12) 0.69447(10) 0.0675(4) Uani 1 1 d . . . . .
Cl5 Cl 0.3834(3) 1.12438(12) 0.51973(10) 0.0810(6) Uani 1 1 d . . . . .
C27 C 0.5523(10) 1.0518(4) 0.5905(4) 0.0562(14) Uani 1 1 d . . . . .
H27 H 0.5349 0.9850 0.5696 0.067 Uiso 1 1 calc R . . . .
O3 O 0.8033(4) 0.61169(19) 0.49708(17) 0.0252(6) Uani 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 C12 1.779(3) . ?
Cl2 C12 1.787(3) . ?
N1 O1 1.206(9) . ?
N1 O2 1.248(9) . ?
N1 C17 1.474(6) . ?
N2 O6 1.218(4) . ?
N2 O7 1.221(4) . ?
N2 C24 1.476(4) . ?
O4 C11 1.446(4) . ?
O4 C20 1.343(4) . ?
O5 C20 1.203(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C4 1.536(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C4 1.529(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.533(6) . ?
C4 C5 1.528(5) . ?
C5 C6 1.376(6) . ?
C5 C10 1.392(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(5) . ?
C8 C9 1.385(5) . ?
C8 C11 1.508(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(6) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.533(5) . ?
C12 C13 1.549(5) . ?
C13 H13 1.0000 . ?
C13 C14 1.510(5) . ?
C13 O3 1.414(4) . ?
C14 C15 1.391(5) . ?
C14 C19 1.387(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(7) . ?
C17 C18 1.371(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.478(4) . ?
C21 C22 1.391(5) . ?
C21 C26 1.384(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(5) . ?
C24 C25 1.379(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(5) . ?
C26 H26 0.9500 . ?
Cl3 C27 1.750(7) . ?
Cl4 C27 1.745(6) . ?
Cl5 C27 1.756(6) . ?
C27 H27 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 124.4(5) . . ?
O1 N1 C17 118.4(6) . . ?
O2 N1 C17 117.2(6) . . ?
O6 N2 O7 124.1(3) . . ?
O6 N2 C24 118.2(3) . . ?
O7 N2 C24 117.8(3) . . ?
C20 O4 C11 115.9(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C2 C4 C1 108.2(4) . . ?
C2 C4 C3 108.2(4) . . ?
C3 C4 C1 109.0(4) . . ?
C5 C4 C1 110.9(3) . . ?
C5 C4 C2 111.9(4) . . ?
C5 C4 C3 108.7(3) . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 C10 116.5(3) . . ?
C10 C5 C4 121.5(3) . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.9(4) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C11 119.8(3) . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 C11 122.3(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 H10 118.8 . . ?
C9 C10 C5 122.4(3) . . ?
C9 C10 H10 118.8 . . ?
O4 C11 C8 109.8(3) . . ?
O4 C11 H11 108.1 . . ?
O4 C11 C12 104.3(3) . . ?
C8 C11 H11 108.1 . . ?
C8 C11 C12 118.0(3) . . ?
C12 C11 H11 108.1 . . ?
Cl1 C12 Cl2 108.05(18) . . ?
C11 C12 Cl1 107.4(2) . . ?
C11 C12 Cl2 111.0(2) . . ?
C11 C12 C13 111.0(3) . . ?
C13 C12 Cl1 110.5(2) . . ?
C13 C12 Cl2 108.8(2) . . ?
C12 C13 H13 108.4 . . ?
C14 C13 C12 114.6(3) . . ?
C14 C13 H13 108.4 . . ?
O3 C13 C12 107.4(3) . . ?
O3 C13 H13 108.4 . . ?
O3 C13 C14 109.5(3) . . ?
C15 C14 C13 121.0(3) . . ?
C19 C14 C13 120.2(3) . . ?
C19 C14 C15 118.8(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(4) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 N1 119.0(5) . . ?
C16 C17 C18 122.8(4) . . ?
C18 C17 N1 118.2(5) . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(4) . . ?
C19 C18 H18 120.9 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.9(4) . . ?
C18 C19 H19 119.5 . . ?
O4 C20 C21 112.3(3) . . ?
O5 C20 O4 123.2(3) . . ?
O5 C20 C21 124.5(3) . . ?
C22 C21 C20 121.6(3) . . ?
C26 C21 C20 118.3(3) . . ?
C26 C21 C22 120.0(3) . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.8 . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 H23 120.8 . . ?
C23 C24 N2 118.5(3) . . ?
C23 C24 C25 123.4(3) . . ?
C25 C24 N2 118.1(3) . . ?
C24 C25 H25 121.3 . . ?
C24 C25 C26 117.4(3) . . ?
C26 C25 H25 121.3 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.3(3) . . ?
C25 C26 H26 119.4 . . ?
Cl3 C27 Cl5 109.9(3) . . ?
Cl3 C27 H27 108.9 . . ?
Cl4 C27 Cl3 110.1(3) . . ?
Cl4 C27 Cl5 110.2(4) . . ?
Cl4 C27 H27 108.9 . . ?
Cl5 C27 H27 108.9 . . ?

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 C12 C13 C14 60.6(3) . . . . ?
Cl1 C12 C13 O3 -61.3(3) . . . . ?
Cl2 C12 C13 C14 -57.9(3) . . . . ?
Cl2 C12 C13 O3 -179.8(2) . . . . ?
N1 C17 C18 C19 -177.6(4) . . . . ?
N2 C24 C25 C26 179.7(3) . . . . ?
O1 N1 C17 C16 -12.1(7) . . . . ?
O1 N1 C17 C18 166.8(5) . . . . ?
O2 N1 C17 C16 170.3(4) . . . . ?
O2 N1 C17 C18 -10.8(6) . . . . ?
O4 C11 C12 Cl1 -179.6(2) . . . . ?
O4 C11 C12 Cl2 -61.7(3) . . . . ?
O4 C11 C12 C13 59.5(3) . . . . ?
O4 C20 C21 C22 8.1(5) . . . . ?
O4 C20 C21 C26 -174.6(3) . . . . ?
O5 C20 C21 C22 -170.4(4) . . . . ?
O5 C20 C21 C26 6.9(6) . . . . ?
O6 N2 C24 C23 11.7(5) . . . . ?
O6 N2 C24 C25 -168.6(3) . . . . ?
O7 N2 C24 C23 -168.5(3) . . . . ?
O7 N2 C24 C25 11.2(5) . . . . ?
C1 C4 C5 C6 -31.2(6) . . . . ?
C1 C4 C5 C10 151.7(5) . . . . ?
C2 C4 C5 C6 -152.1(4) . . . . ?
C2 C4 C5 C10 30.9(5) . . . . ?
C3 C4 C5 C6 88.5(5) . . . . ?
C3 C4 C5 C10 -88.5(5) . . . . ?
C4 C5 C6 C7 -177.7(4) . . . . ?
C4 C5 C10 C9 178.0(4) . . . . ?
C5 C6 C7 C8 -0.4(6) . . . . ?
C6 C5 C10 C9 0.8(7) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
C6 C7 C8 C11 176.3(4) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C7 C8 C11 O4 -141.6(3) . . . . ?
C7 C8 C11 C12 99.1(4) . . . . ?
C8 C9 C10 C5 -0.4(7) . . . . ?
C8 C11 C12 Cl1 -57.5(3) . . . . ?
C8 C11 C12 Cl2 60.4(3) . . . . ?
C8 C11 C12 C13 -178.4(3) . . . . ?
C9 C8 C11 O4 33.7(5) . . . . ?
C9 C8 C11 C12 -85.6(4) . . . . ?
C10 C5 C6 C7 -0.5(6) . . . . ?
C11 O4 C20 O5 7.9(5) . . . . ?
C11 O4 C20 C21 -170.7(3) . . . . ?
C11 C8 C9 C10 -175.8(4) . . . . ?
C11 C12 C13 C14 179.6(3) . . . . ?
C11 C12 C13 O3 57.7(3) . . . . ?
C12 C13 C14 C15 -89.3(4) . . . . ?
C12 C13 C14 C19 94.5(4) . . . . ?
C13 C14 C15 C16 -175.3(3) . . . . ?
C13 C14 C19 C18 175.8(3) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 C14 C19 C18 -0.5(5) . . . . ?
C15 C16 C17 N1 178.0(4) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C17 C18 C19 1.3(6) . . . . ?
C17 C18 C19 C14 -0.6(6) . . . . ?
C19 C14 C15 C16 1.0(6) . . . . ?
C20 O4 C11 C8 81.8(3) . . . . ?
C20 O4 C11 C12 -150.8(3) . . . . ?
C20 C21 C22 C23 176.2(3) . . . . ?
C20 C21 C26 C25 -177.7(3) . . . . ?
C21 C22 C23 C24 1.5(5) . . . . ?
C22 C21 C26 C25 -0.3(6) . . . . ?
C22 C23 C24 N2 178.9(3) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C26 -0.6(6) . . . . ?
C24 C25 C26 C21 1.1(6) . . . . ?
C26 C21 C22 C23 -1.0(5) . . . . ?
O3 C13 C14 C15 31.4(4) . . . . ?
O3 C13 C14 C19 -144.8(3) . . . . ?

_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_mjh130005
_database_code_depnum_ccdc_archive 'CCDC 1020138'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'((2R*,3R*)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(1-methyl-1H-pyrrol-2-yl)methanone '
_chemical_formula_moiety         'C14 H11 Cl N2 O4'
_chemical_formula_sum            'C14 H11 Cl N2 O4'
_chemical_formula_weight         306.70
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4142(4)
_cell_length_b                   21.2032(8)
_cell_length_c                   8.5672(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.111(6)
_cell_angle_gamma                90
_cell_volume                     1372.47(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5809
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5389
_cell_measurement_theta_min      2.8563
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14096
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.602
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  102.0000 -137.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00  -50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632  -57.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000 -180.0000 106

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00   48.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   57.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   17.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -99.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega  -16.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000    0.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0184157000
_diffrn_orient_matrix_UB_12      -0.0315988000
_diffrn_orient_matrix_UB_13      0.0137360000
_diffrn_orient_matrix_UB_21      0.0912128000
_diffrn_orient_matrix_UB_22      -0.0050279000
_diffrn_orient_matrix_UB_23      0.0546594000
_diffrn_orient_matrix_UB_31      -0.0126800000
_diffrn_orient_matrix_UB_32      0.0097336000
_diffrn_orient_matrix_UB_33      0.0729432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2729
_reflns_number_total             3057
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.074
_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)+(0.0322P)²+0.8344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          
;
A minor disorder component is present, of
 approximately 6.5% requiring the use of a
 moderate number of restraints to maintain
 chemical sense in the minor component, If this
 disorder is omitted the residual factors increase by
 > 1% and residual e density is sub optimal.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C6A \\sim C7-C6
 with sigma of 0.02
 O2A-C8 \\sim O2-C8
 with sigma of 0.02
 O2-C7 \\sim O2A-C7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
Uanis(C6) = Uanis(C6A)
Uanis(C5) = Uanis(C5A)
Uanis(C4) = Uanis(C4A)
Uanis(C3) = Uanis(C3A)
Uanis(C2) = Uanis(C2A)
Uanis(N1) = Uanis(N1A)
Uanis(C1) = Uanis(C1A)
4. Same fragment restrains
{O1, C6, C5, C4, C3, C2, N1, C1}
as
{O1A, C6A, C5A, C4A, C3A, C2A, N1A, C1A}
5. Others
 Sof(H8B)=Sof(O1A)=Sof(C6A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=
 Sof(C2A)=Sof(H2A)=Sof(N1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O2A)=1-
 FVAR(1)
 Sof(O1)=Sof(C6)=Sof(C5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=
 Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(O2)=Sof(H8A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C4A(H4A),
 C3A(H3A), C2A(H2A)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.68010(5) 0.11282(2) 0.18412(5) 0.03262(13) Uani 1 1 d . . . . .
O1 O 0.88041(16) 0.04936(6) 0.59613(17) 0.0334(3) Uani 0.9347(13) 1 d . . P A 1
C6 C 0.8851(2) 0.10017(8) 0.5320(2) 0.0219(3) Uani 0.9347(13) 1 d . . P A 1
C5 C 1.0401(2) 0.13732(14) 0.5698(8) 0.0225(4) Uani 0.9347(13) 1 d . . P A 1
C4 C 1.0528(2) 0.19701(8) 0.5081(2) 0.0292(4) Uani 0.9347(13) 1 d . . P A 1
H4 H 0.9572 0.2217 0.4288 0.035 Uiso 0.9347(13) 1 calc R . P A 1
C3 C 1.2311(4) 0.21387(19) 0.5838(9) 0.0351(5) Uani 0.9347(13) 1 d . . P A 1
H3 H 1.2795 0.2521 0.5659 0.042 Uiso 0.9347(13) 1 calc R . P A 1
C2 C 1.3239(2) 0.16458(9) 0.6895(2) 0.0306(4) Uani 0.9347(13) 1 d . . P A 1
H2 H 1.4486 0.1633 0.7570 0.037 Uiso 0.9347(13) 1 calc R . P A 1
N1 N 1.21042(18) 0.11836(7) 0.68239(18) 0.0244(3) Uani 0.9347(13) 1 d . . P A 1
C1 C 1.2643(3) 0.05857(9) 0.7730(3) 0.0336(6) Uani 0.9347(13) 1 d . . P A 1
H1A H 1.2234 0.0562 0.8638 0.050 Uiso 0.9347(13) 1 calc GR . P A 1
H1B H 1.3936 0.0552 0.8261 0.050 Uiso 0.9347(13) 1 calc GR . P A 1
H1C H 1.2121 0.0239 0.6904 0.050 Uiso 0.9347(13) 1 calc GR . P A 1
N2 N -0.15718(17) 0.11562(7) -0.08865(17) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.65755(15) 0.18683(6) 0.43074(16) 0.0299(3) Uani 0.9347(13) 1 d . . P A 1
O3 O -0.23883(15) 0.06624(6) -0.10558(15) 0.0348(3) Uani 1 1 d . . . . .
O4 O -0.22329(16) 0.16313(6) -0.17501(15) 0.0371(3) Uani 1 1 d . . . . .
C7 C 0.7095(2) 0.12737(7) 0.39732(19) 0.0217(3) Uani 1 1 d . . . . .
C8 C 0.5539(2) 0.13188(8) 0.4309(2) 0.0248(3) Uani 1 1 d . . . . .
H8A H 0.5714 0.1171 0.5482 0.030 Uiso 0.9347(13) 1 calc R . P A 1
H8B H 0.5687 0.1620 0.5261 0.030 Uiso 0.0653(13) 1 calc R . P A 2
C9 C 0.3697(2) 0.12790(8) 0.29175(19) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.3000(2) 0.17462(8) 0.1662(2) 0.0279(3) Uani 1 1 d . . . . .
H10 H 0.3714 0.2094 0.1666 0.034 Uiso 1 1 calc R . . . .
C11 C 0.1265(2) 0.17054(8) 0.0403(2) 0.0277(3) Uani 1 1 d . . . . .
H11 H 0.0768 0.2025 -0.0455 0.033 Uiso 1 1 calc R . . . .
C12 C 0.02750(19) 0.11906(7) 0.04235(19) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.0933(2) 0.07166(7) 0.1644(2) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.0220 0.0365 0.1617 0.030 Uiso 1 1 calc R . . . .
C14 C 0.2660(2) 0.07677(8) 0.2908(2) 0.0263(3) Uani 1 1 d . . . . .
H14 H 0.3141 0.0451 0.3776 0.032 Uiso 1 1 calc R . . . .
O1A O 0.866(2) 0.2194(7) 0.452(2) 0.0334(3) Uani 0.0653(13) 1 d . . P A 2
C6A C 0.8793(18) 0.1632(7) 0.480(3) 0.0219(3) Uani 0.0653(13) 1 d . . P A 2
C5A C 1.037(2) 0.1280(17) 0.581(12) 0.0225(4) Uani 0.0653(13) 1 d . . P A 2
C4A C 1.056(2) 0.0658(8) 0.641(3) 0.0292(4) Uani 0.0653(13) 1 d . . P A 2
H4A H 0.9627 0.0374 0.6258 0.035 Uiso 0.0653(13) 1 calc R . P A 2
C3A C 1.239(3) 0.0530(11) 0.727(6) 0.0351(5) Uani 0.0653(13) 1 d . . P A 2
H3A H 1.2928 0.0134 0.7711 0.042 Uiso 0.0653(13) 1 calc R . P A 2
C2A C 1.324(2) 0.1096(9) 0.736(3) 0.0306(4) Uani 0.0653(13) 1 d . . P A 2
H2A H 1.4478 0.1161 0.7987 0.037 Uiso 0.0653(13) 1 calc R . P A 2
N1A N 1.207(2) 0.1536(8) 0.646(2) 0.0244(3) Uani 0.0653(13) 1 d . . P A 2
C1A C 1.249(6) 0.214(3) 0.589(13) 0.0336(6) Uani 0.0653(13) 1 d . . P A 2
H1AA H 1.1823 0.2172 0.4623 0.050 Uiso 0.0653(13) 1 calc GR . P A 2
H1AB H 1.3764 0.2153 0.6208 0.050 Uiso 0.0653(13) 1 calc GR . P A 2
H1AC H 1.2176 0.2483 0.6449 0.050 Uiso 0.0653(13) 1 calc GR . P A 2
O2A O 0.659(2) 0.0797(6) 0.487(2) 0.0299(3) Uani 0.0653(13) 1 d . . P A 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
Cl C7 1.7593(15) . ?
O1 C6 1.218(2) . ?
C6 C5 1.434(2) . ?
C6 C7 1.532(2) . ?
C5 C4 1.393(3) . ?
C5 N1 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.394(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.378(4) . ?
C2 H2 0.9500 . ?
C2 N1 1.351(2) . ?
N1 C1 1.451(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N2 O3 1.2255(18) . ?
N2 O4 1.2285(18) . ?
N2 C12 1.4644(19) . ?
O2 C7 1.4045(19) . ?
O2 C8 1.456(2) . ?
C7 C8 1.462(2) . ?
C7 C6A 1.493(14) . ?
C7 O2A 1.443(14) . ?
C8 H8A 1.0000 . ?
C8 H8B 1.0000 . ?
C8 C9 1.485(2) . ?
C8 O2A 1.365(13) . ?
C9 C10 1.388(2) . ?
C9 C14 1.389(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(2) . ?
C12 C13 1.378(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
O1A C6A 1.211(15) . ?
C6A C5A 1.431(14) . ?
C5A C4A 1.400(16) . ?
C5A N1A 1.403(16) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.411(17) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.383(17) . ?
C2A H2A 0.9500 . ?
C2A N1A 1.328(15) . ?
N1A C1A 1.459(16) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 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 C6 C5 126.22(16) . . ?
O1 C6 C7 117.47(14) . . ?
C5 C6 C7 116.31(15) . . ?
C4 C5 C6 128.86(17) . . ?
N1 C5 C6 123.78(18) . . ?
N1 C5 C4 107.35(16) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 C5 107.65(19) . . ?
C3 C4 H4 126.2 . . ?
C4 C3 H3 126.5 . . ?
C2 C3 C4 107.08(18) . . ?
C2 C3 H3 126.5 . . ?
C3 C2 H2 125.2 . . ?
N1 C2 C3 109.61(18) . . ?
N1 C2 H2 125.2 . . ?
C5 N1 C1 127.46(16) . . ?
C2 N1 C5 108.31(16) . . ?
C2 N1 C1 124.17(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 N2 O4 123.20(13) . . ?
O3 N2 C12 118.93(13) . . ?
O4 N2 C12 117.86(13) . . ?
C7 O2 C8 61.43(10) . . ?
C6 C7 Cl 111.37(11) . . ?
O2 C7 Cl 117.06(11) . . ?
O2 C7 C6 117.90(12) . . ?
O2 C7 C8 61.00(10) . . ?
C8 C7 Cl 119.13(11) . . ?
C8 C7 C6 121.79(13) . . ?
C8 C7 C6A 128.9(8) . . ?
C6A C7 Cl 104.4(8) . . ?
O2A C7 Cl 119.4(7) . . ?
O2A C7 C8 56.0(6) . . ?
O2A C7 C6A 123.3(10) . . ?
O2 C8 C7 57.56(10) . . ?
O2 C8 H8A 115.4 . . ?
O2 C8 C9 117.32(13) . . ?
C7 C8 H8A 115.4 . . ?
C7 C8 H8B 113.7 . . ?
C7 C8 C9 123.19(13) . . ?
C9 C8 H8A 115.4 . . ?
C9 C8 H8B 113.7 . . ?
O2A C8 C7 61.3(6) . . ?
O2A C8 H8B 113.7 . . ?
O2A C8 C9 121.5(7) . . ?
C10 C9 C8 121.15(14) . . ?
C10 C9 C14 120.15(14) . . ?
C14 C9 C8 118.69(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.00(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.41(14) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 N2 118.24(14) . . ?
C11 C12 C13 122.97(14) . . ?
C13 C12 N2 118.77(14) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.01(14) . . ?
C14 C13 H13 121.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.45(14) . . ?
C13 C14 H14 119.8 . . ?
O1A C6A C7 114.8(12) . . ?
O1A C6A C5A 127.9(15) . . ?
C5A C6A C7 117.3(14) . . ?
C4A C5A C6A 129.7(15) . . ?
C4A C5A N1A 106.7(10) . . ?
N1A C5A C6A 123.5(14) . . ?
C5A C4A H4A 126.3 . . ?
C5A C4A C3A 107.3(11) . . ?
C3A C4A H4A 126.3 . . ?
C4A C3A H3A 126.9 . . ?
C2A C3A C4A 106.3(11) . . ?
C2A C3A H3A 126.9 . . ?
C3A C2A H2A 124.8 . . ?
N1A C2A C3A 110.3(11) . . ?
N1A C2A H2A 124.8 . . ?
C5A N1A C1A 124.1(18) . . ?
C2A N1A C5A 108.9(10) . . ?
C2A N1A C1A 125.7(18) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C8 O2A C7 62.7(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_a C6_a C5_a N1_a 2.8(8) . . . . ?
C7 C6 C5 N1 -176.9(4) . . . . ?
O1 C6 C5 C4 -176.2(4) . . . . ?
C7 C6 C5 C4 4.1(7) . . . . ?
N1 C5 C4 C3 0.0(6) . . . . ?
C6 C5 C4 C3 179.1(6) . . . . ?
C5 C4 C3 C2 0.1(6) . . . . ?
C4 C3 C2 N1 -0.2(6) . . . . ?
C3 C2 N1 C5 0.2(5) . . . . ?
C3 C2 N1 C1 177.6(4) . . . . ?
C4 C5 N1 C2 -0.1(5) . . . . ?
C6 C5 N1 C2 -179.3(4) . . . . ?
C4 C5 N1 C1 -177.5(2) . . . . ?
C6 C5 N1 C1 3.4(8) . . . . ?
C8 O2 C7 O2A -29.6(7) . . . . ?
C8 O2 C7 C6A -150.6(8) . . . . ?
C8 O2 C7 C6 -112.83(15) . . . . ?
C8 O2 C7 Cl 110.00(13) . . . . ?
O1 C6 C7 O2 121.68(16) . . . . ?
C5 C6 C7 O2 -58.6(4) . . . . ?
O1 C6 C7 O2A 17.4(7) . . . . ?
C5 C6 C7 O2A -162.9(7) . . . . ?
O1 C6 C7 C8 50.2(2) . . . . ?
C5 C6 C7 C8 -130.1(3) . . . . ?
O1 C6 C7 C6A 168.1(10) . . . . ?
C5 C6 C7 C6A -12.2(11) . . . . ?
O1 C6 C7 Cl -98.87(15) . . . . ?
C5 C6 C7 Cl 80.9(3) . . . . ?
C7 O2 C8 O2A 31.8(8) . . . . ?
C7 O2 C8 C9 -113.69(15) . . . . ?
O2 C7 C8 O2A -145.8(8) . . . . ?
C6A C7 C8 O2A -108.0(11) . . . . ?
C6 C7 C8 O2A -39.1(8) . . . . ?
Cl C7 C8 O2A 107.6(8) . . . . ?
O2A C7 C8 O2 145.8(8) . . . . ?
C6A C7 C8 O2 37.8(8) . . . . ?
C6 C7 C8 O2 106.62(15) . . . . ?
Cl C7 C8 O2 -106.65(13) . . . . ?
O2 C7 C8 C9 103.53(17) . . . . ?
O2A C7 C8 C9 -110.7(8) . . . . ?
C6A C7 C8 C9 141.3(8) . . . . ?
C6 C7 C8 C9 -149.85(15) . . . . ?
Cl C7 C8 C9 -3.1(2) . . . . ?
O2A C8 C9 C10 -141.2(8) . . . . ?
O2 C8 C9 C10 0.4(2) . . . . ?
C7 C8 C9 C10 -67.0(2) . . . . ?
O2A C8 C9 C14 39.9(8) . . . . ?
O2 C8 C9 C14 -178.48(14) . . . . ?
C7 C8 C9 C14 114.07(18) . . . . ?
C14 C9 C10 C11 0.4(2) . . . . ?
C8 C9 C10 C11 -178.46(15) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C10 C11 C12 N2 178.66(14) . . . . ?
O3 N2 C12 C11 169.08(14) . . . . ?
O4 N2 C12 C11 -11.8(2) . . . . ?
O3 N2 C12 C13 -12.4(2) . . . . ?
O4 N2 C12 C13 166.63(14) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
N2 C12 C13 C14 -177.76(13) . . . . ?
C12 C13 C14 C9 -1.0(2) . . . . ?
C10 C9 C14 C13 0.5(2) . . . . ?
C8 C9 C14 C13 179.41(14) . . . . ?
O2 C7 C6A O1A -31.0(17) . . . . ?
O2A C7 C6A O1A -135.3(17) . . . . ?
C8 C7 C6A O1A -65(2) . . . . ?
C6 C7 C6A O1A -170(2) . . . . ?
Cl C7 C6A O1A 83.9(19) . . . . ?
O2 C7 C6A C5A 149(5) . . . . ?
O2A C7 C6A C5A 45(5) . . . . ?
C8 C7 C6A C5A 115(5) . . . . ?
C6 C7 C6A C5A 10(5) . . . . ?
Cl C7 C6A C5A -96(5) . . . . ?
O1A C6A C5A C4A 168(7) . . . . ?
C7 C6A C5A C4A -12(12) . . . . ?
O1A C6A C5A N1A -9(12) . . . . ?
C7 C6A C5A N1A 171(6) . . . . ?
N1A C5A C4A C3A -5(8) . . . . ?
C6A C5A C4A C3A 177(9) . . . . ?
C5A C4A C3A C2A 7(6) . . . . ?
C4A C3A C2A N1A -7(4) . . . . ?
C3A C2A N1A C5A 3(6) . . . . ?
C3A C2A N1A C1A -164(7) . . . . ?
C4A C5A N1A C2A 1(8) . . . . ?
C6A C5A N1A C2A 179(7) . . . . ?
C4A C5A N1A C1A 169(7) . . . . ?
C6A C5A N1A C1A -14(13) . . . . ?
O2 C8 O2A C7 -30.5(7) . . . . ?
C9 C8 O2A C7 113.3(4) . . . . ?
O2 C7 O2A C8 31.4(7) . . . . ?
C6A C7 O2A C8 117.5(10) . . . . ?
C6 C7 O2A C8 146.3(6) . . . . ?
Cl C7 O2A C8 -107.1(5) . . . . ?

_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_mjh130018
_database_code_depnum_ccdc_archive 'CCDC 1020139'
_audit_update_record             
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2013-08-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2013.07.19 svn.r2750, GUI svn.r4539)
;
_chemical_name_common            ?
_chemical_name_systematic        
'((2R*,3R*)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(p-tolyl)methanone '
_chemical_formula_moiety         'C16 H12 Cl N O4'
_chemical_formula_sum            'C16 H12 Cl N O4'
_chemical_formula_weight         317.72
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   15.660(2)
_cell_length_b                   7.1579(10)
_cell_length_c                   14.548(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.366(4)
_cell_angle_gamma                90
_cell_volume                     1497.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8225
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.83
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1048 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.8844.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.41
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 3 sets of ω scans each set at different φ angles and each
 scan (15 s exposure) covering -0.5° degrees in ω. The crystal to detector 
 distance was 45 mm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9693
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_min         2.834
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker Photon 100 Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3274
_reflns_number_total             3415
_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       'Apex2 - SAINT (Bruker 2013)'
_computing_data_collection       'Apex2 (Bruker 2013)'
_computing_data_reduction        'Apex2 - SAINT (Bruker 2013)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.074
_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)+(0.0377P)²+0.6003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0770
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.81327(4) 0.30962(9) 0.72199(4) 0.03802(17) Uani 1 1 d . . . . .
O1 O 0.59383(16) 0.1103(3) 0.60071(16) 0.0471(5) Uani 1 1 d . . . . .
O2 O 0.68917(13) 0.2219(2) 0.79935(13) 0.0335(4) Uani 1 1 d . . . . .
O3 O 0.98825(14) 0.8195(3) 1.16382(15) 0.0454(5) Uani 1 1 d . . . . .
O4 O 0.90935(17) 1.0610(3) 1.08888(16) 0.0513(5) Uani 1 1 d . . . . .
N1 N 0.92460(16) 0.8928(3) 1.09433(16) 0.0358(5) Uani 1 1 d . . . . .
C1 C 0.4947(2) 0.8529(5) 0.3214(3) 0.0546(8) Uani 1 1 d . . . . .
H1A H 0.4789 0.8031 0.2539 0.082 Uiso 1 1 calc R U . . .
H1B H 0.5413 0.9520 0.3347 0.082 Uiso 1 1 calc R U . . .
H1C H 0.4387 0.9039 0.3265 0.082 Uiso 1 1 calc R U . . .
C2 C 0.53350(19) 0.6990(4) 0.3967(2) 0.0393(6) Uani 1 1 d . . . . .
C3 C 0.49401(19) 0.5217(4) 0.3782(2) 0.0415(6) Uani 1 1 d . . . . .
H3 H 0.4434 0.4977 0.3164 0.050 Uiso 1 1 calc R U . . .
C4 C 0.52653(18) 0.3810(4) 0.4473(2) 0.0386(6) Uani 1 1 d . . . . .
H4 H 0.4988 0.2606 0.4326 0.046 Uiso 1 1 calc R U . . .
C5 C 0.60067(16) 0.4141(4) 0.53952(18) 0.0310(5) Uani 1 1 d . . . . .
C6 C 0.64101(17) 0.5908(4) 0.55868(19) 0.0332(5) Uani 1 1 d . . . . .
H6 H 0.6912 0.6155 0.6208 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6083(2) 0.7303(4) 0.4877(2) 0.0381(6) Uani 1 1 d . . . . .
H7 H 0.6373 0.8496 0.5010 0.046 Uiso 1 1 calc R U . . .
C8 C 0.62777(17) 0.2637(4) 0.61553(19) 0.0323(5) Uani 1 1 d . . . . .
C9 C 0.69981(16) 0.3097(3) 0.71935(18) 0.0275(5) Uani 1 1 d . . . . .
C10 C 0.67651(15) 0.4236(3) 0.79016(17) 0.0256(4) Uani 1 1 d . . . . .
H10 H 0.6104 0.4666 0.7649 0.031 Uiso 1 1 calc R U . . .
C11 C 0.74392(15) 0.5430(3) 0.86878(16) 0.0244(4) Uani 1 1 d . . . . .
C12 C 0.82205(16) 0.4688(3) 0.94481(17) 0.0278(5) Uani 1 1 d . . . . .
H12 H 0.8341 0.3385 0.9462 0.033 Uiso 1 1 calc R U . . .
C13 C 0.88240(16) 0.5832(4) 1.01838(16) 0.0290(5) Uani 1 1 d . . . . .
H13 H 0.9359 0.5334 1.0706 0.035 Uiso 1 1 calc R U . . .
C14 C 0.86292(17) 0.7716(4) 1.01398(17) 0.0274(5) Uani 1 1 d . . . . .
C15 C 0.78660(18) 0.8501(3) 0.93898(18) 0.0314(5) Uani 1 1 d . . . . .
H15 H 0.7755 0.9808 0.9375 0.038 Uiso 1 1 calc R U . . .
C16 C 0.72657(17) 0.7335(3) 0.86590(18) 0.0297(5) Uani 1 1 d . . . . .
H16 H 0.6733 0.7842 0.8136 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.762(2) . ?
O1 C8 1.201(3) . ?
O2 C9 1.390(3) . ?
O2 C10 1.456(3) . ?
O3 N1 1.221(3) . ?
O4 N1 1.224(3) . ?
N1 C14 1.468(3) . ?
C1 C2 1.502(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.394(4) . ?
C3 C4 1.370(4) . ?
C4 C5 1.403(4) . ?
C5 C6 1.391(3) . ?
C5 C8 1.480(4) . ?
C6 C7 1.381(4) . ?
C8 C9 1.520(3) . ?
C9 C10 1.468(3) . ?
C10 C11 1.482(3) . ?
C11 C12 1.389(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.379(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.385(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
C9 O2 C10 62.07(14) . . ?
O3 N1 O4 123.4(2) . . ?
O3 N1 C14 118.0(2) . . ?
O4 N1 C14 118.7(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 C7 118.2(3) . . ?
C7 C2 C1 121.2(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 C8 118.3(2) . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 C8 122.6(2) . . ?
C7 C6 C5 120.2(2) . . ?
C6 C7 C2 121.1(3) . . ?
O1 C8 C5 123.7(2) . . ?
O1 C8 C9 118.5(2) . . ?
C5 C8 C9 117.7(2) . . ?
O2 C9 Cl1 115.87(17) . . ?
O2 C9 C8 116.5(2) . . ?
O2 C9 C10 61.18(15) . . ?
C8 C9 Cl1 111.47(16) . . ?
C10 C9 Cl1 120.93(17) . . ?
C10 C9 C8 121.6(2) . . ?
O2 C10 C9 56.75(14) . . ?
O2 C10 C11 118.15(18) . . ?
C9 C10 C11 124.23(19) . . ?
C12 C11 C10 121.8(2) . . ?
C16 C11 C10 118.2(2) . . ?
C16 C11 C12 120.0(2) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 118.2(2) . . ?
C13 C14 N1 118.5(2) . . ?
C15 C14 N1 118.7(2) . . ?
C15 C14 C13 122.8(2) . . ?
C14 C15 C16 118.3(2) . . ?
C15 C16 C11 120.2(2) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-3
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mjh140034_fa
_database_code_depnum_ccdc_archive 'CCDC 1037684'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_audit_creation_date             2014-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3107 for OlexSys, GUI svn.r4957)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'((2R*,3R*)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(phenyl)methanone '
_chemical_formula_moiety         'C15 H10 Cl N O4'
_chemical_formula_sum            'C15 H10 Cl N O4'
_chemical_formula_weight         303.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H10 N1 O4 Cl1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.32300(9)
_cell_length_b                   12.09364(16)
_cell_length_c                   15.09304(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.2048(10)
_cell_angle_gamma                90
_cell_volume                     1328.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12863
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.0420
_cell_measurement_theta_min      3.3630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40662
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         3.266
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   19.0000 -120.0000 132

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   57.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00   13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  150.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  5 omega  -58.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
  6 omega  -96.00   15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  -90.0000 111

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596 -178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega    4.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -99.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  9 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 10 omega  -50.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440   38.0000   90.0000 106

#__ type_ start__ end____ width___ exp.time_
 11 omega  -94.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -57.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
 12 omega  -55.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -38.0000  -90.0000 117

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   -4.00   71.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  -99.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 15 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 16 omega   -8.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596   57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 17 omega   53.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596 -178.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
 19 omega   57.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596  178.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 20 omega  -15.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596   77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
 21 omega  -96.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440  -77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
 22 omega -107.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.9440 -178.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
 23 omega  -59.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       21.9596    0.0000 -180.0000 42
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0156100000
_diffrn_orient_matrix_UB_12      -0.0550907000
_diffrn_orient_matrix_UB_13      0.0134342000
_diffrn_orient_matrix_UB_21      -0.0898150000
_diffrn_orient_matrix_UB_22      0.0148015000
_diffrn_orient_matrix_UB_23      0.0091389000
_diffrn_orient_matrix_UB_31      -0.0344246000
_diffrn_orient_matrix_UB_32      -0.0136176000
_diffrn_orient_matrix_UB_33      -0.0443869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2518
_reflns_number_total             3041
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.028
_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)+(0.0281P)²+0.6421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.84437(5) 0.37756(3) 0.49525(2) 0.03349(11) Uani 1 1 d . . . . .
O1 O 0.17036(16) -0.03238(9) 0.56086(8) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.10135(15) 0.10844(10) 0.63910(7) 0.0396(3) Uani 1 1 d . . . . .
O3 O 0.57515(14) 0.46301(8) 0.38015(7) 0.0323(3) Uani 1 1 d . . . . .
O4 O 0.89727(16) 0.53153(9) 0.30946(8) 0.0377(3) Uani 1 1 d . . . . .
N1 N 0.17478(16) 0.06674(11) 0.57754(8) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.27370(17) 0.14025(12) 0.52151(9) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.35000(19) 0.09405(12) 0.44997(9) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.3387 0.0188 0.4379 0.032 Uiso 1 1 calc R . . . .
C3 C 0.44334(19) 0.16256(12) 0.39701(9) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.4946 0.1335 0.3483 0.031 Uiso 1 1 calc R . . . .
C4 C 0.46088(17) 0.27453(12) 0.41627(9) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.38305(19) 0.31834(12) 0.48869(9) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.3948 0.3934 0.5014 0.033 Uiso 1 1 calc R . . . .
C6 C 0.28814(19) 0.25079(12) 0.54200(9) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.2355 0.2795 0.5904 0.032 Uiso 1 1 calc R . . . .
C7 C 0.56070(18) 0.34619(12) 0.35758(9) 0.0247(3) Uani 1 1 d . . . . .
H7 H 0.5394 0.3295 0.2938 0.030 Uiso 1 1 calc R . . . .
C8 C 0.73612(19) 0.40062(11) 0.38695(9) 0.0235(3) Uani 1 1 d . . . . .
C9 C 0.87792(19) 0.43405(12) 0.32474(9) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.98110(18) 0.34468(11) 0.28561(9) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.95001(18) 0.23379(12) 0.30373(9) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.8676 0.2148 0.3440 0.029 Uiso 1 1 calc R . . . .
C12 C 1.0410(2) 0.15173(12) 0.26224(9) 0.0283(3) Uani 1 1 d . . . . .
H12 H 1.0202 0.0777 0.2746 0.034 Uiso 1 1 calc R . . . .
C13 C 1.1635(2) 0.18025(13) 0.20197(9) 0.0304(3) Uani 1 1 d . . . . .
H13 H 1.2233 0.1251 0.1733 0.036 Uiso 1 1 calc R . . . .
C14 C 1.1972(2) 0.29041(13) 0.18432(9) 0.0302(3) Uani 1 1 d . . . . .
H14 H 1.2802 0.3091 0.1443 0.036 Uiso 1 1 calc R . . . .
C15 C 1.10753(19) 0.37233(12) 0.22614(9) 0.0268(3) Uani 1 1 d . . . . .
H15 H 1.1312 0.4462 0.2148 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.7601(14) . ?
O1 N1 1.2245(17) . ?
O2 N1 1.2307(16) . ?
O3 C7 1.4545(17) . ?
O3 C8 1.3940(17) . ?
O4 C9 1.2124(17) . ?
N1 C1 1.4706(17) . ?
C1 C2 1.3859(19) . ?
C1 C6 1.374(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3822(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C4 C5 1.3911(19) . ?
C4 C7 1.4865(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.4686(19) . ?
C8 C9 1.5277(19) . ?
C9 C10 1.478(2) . ?
C10 C11 1.3923(19) . ?
C10 C15 1.3979(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C7 62.03(9) . . ?
O1 N1 O2 123.53(12) . . ?
O1 N1 C1 118.50(12) . . ?
O2 N1 C1 117.97(13) . . ?
C2 C1 N1 118.00(13) . . ?
C6 C1 N1 119.31(12) . . ?
C6 C1 C2 122.68(13) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.37(13) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.27(13) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.97(13) . . ?
C3 C4 C7 118.97(12) . . ?
C5 C4 C7 121.06(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.38(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.32(13) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O3 C7 C4 117.05(11) . . ?
O3 C7 H7 115.4 . . ?
O3 C7 C8 56.96(9) . . ?
C4 C7 H7 115.4 . . ?
C8 C7 C4 123.50(12) . . ?
C8 C7 H7 115.4 . . ?
O3 C8 Cl1 116.52(10) . . ?
O3 C8 C7 61.01(9) . . ?
O3 C8 C9 115.92(11) . . ?
C7 C8 Cl1 120.04(10) . . ?
C7 C8 C9 124.31(12) . . ?
C9 C8 Cl1 110.17(10) . . ?
O4 C9 C8 118.39(13) . . ?
O4 C9 C10 124.03(13) . . ?
C10 C9 C8 117.57(12) . . ?
C11 C10 C9 121.62(12) . . ?
C11 C10 C15 119.36(13) . . ?
C15 C10 C9 118.97(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.36(12) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.71(14) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.38(14) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.96(13) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.22(14) . . ?
C14 C15 H15 119.9 . . ?

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 C8 C9 O4 -98.12(14) . . . . ?
Cl1 C8 C9 C10 82.91(13) . . . . ?
O1 N1 C1 C2 2.88(19) . . . . ?
O1 N1 C1 C6 -176.69(13) . . . . ?
O2 N1 C1 C2 -177.41(13) . . . . ?
O2 N1 C1 C6 3.02(19) . . . . ?
O3 C7 C8 Cl1 105.62(11) . . . . ?
O3 C7 C8 C9 -103.11(14) . . . . ?
O3 C8 C9 O4 36.90(19) . . . . ?
O3 C8 C9 C10 -142.07(13) . . . . ?
O4 C9 C10 C11 -178.34(14) . . . . ?
O4 C9 C10 C15 -1.0(2) . . . . ?
N1 C1 C2 C3 -179.95(12) . . . . ?
N1 C1 C6 C5 179.54(12) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 -179.49(12) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C7 O3 179.80(12) . . . . ?
C3 C4 C7 C8 -113.54(15) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C7 C8 Cl1 2.91(19) . . . . ?
C4 C7 C8 O3 -102.71(14) . . . . ?
C4 C7 C8 C9 154.18(13) . . . . ?
C5 C4 C7 O3 0.84(19) . . . . ?
C5 C4 C7 C8 67.50(18) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 O3 C8 Cl1 -111.30(11) . . . . ?
C7 O3 C8 C9 116.56(13) . . . . ?
C7 C4 C5 C6 179.05(13) . . . . ?
C7 C8 C9 O4 108.19(16) . . . . ?
C7 C8 C9 C10 -70.78(18) . . . . ?
C8 O3 C7 C4 114.03(13) . . . . ?
C8 C9 C10 C11 0.57(19) . . . . ?
C8 C9 C10 C15 177.93(12) . . . . ?
C9 C10 C11 C12 176.30(13) . . . . ?
C9 C10 C15 C14 -175.90(13) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C10 C15 C14 1.5(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 -0.7(2) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
0 1 1 0.0570 0.0000 1.0000 1.0000 -0.0417 0.0239 -0.0580
-1 -2 -1 0.0445 -1.0000 -2.0000 -1.0000 0.1124 0.0511 0.1060
2 1 -2 0.0954 2.0000 1.0000 -2.0000 -0.1132 -0.1831 0.0063
0 1 -1 0.0847 -0.0000 1.0000 -1.0000 -0.0685 0.0057 0.0308
-1 0 -1 0.1330 -1.0000 0.0000 -1.0000 0.0022 0.0807 0.0788
-1 -1 1 0.1125 -1.0000 -1.0000 1.0000 0.0841 0.0842 0.0037
1 0 2 0.1013 1.0000 -0.0000 2.0000 0.0113 -0.0715 -0.1232
0 -1 -1 0.0827 -0.0000 -1.0000 -1.0000 0.0417 -0.0239 0.0580
-1 -3 0 0.0691 -1.0000 -3.0000 -0.0000 0.1809 0.0454 0.0753

_olex2_submission_special_instructions 'No special instructions were received'
