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

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

data_rh061
_database_code_depnum_ccdc_archive 'CCDC 1854641'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_date             2015-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H13 N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.8314(4)
_cell_length_b                   9.9500(6)
_cell_length_c                   10.2599(6)
_cell_angle_alpha                71.126(6)
_cell_angle_beta                 76.243(6)
_cell_angle_gamma                77.203(6)
_cell_volume                     540.33(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2855
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8420
_cell_measurement_theta_min      4.5880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 -1 0.0198
0 6 1 0.0198
4 0 3 0.1590
-3 -5 -3 0.1492
0 -2 -7 0.0743
3 4 0 0.1109
-2 -1 4 0.0767
0 2 7 0.0990
2 4 6 0.1254

_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0007 -6.0016 -1.0038 0.0220 0.8235 -0.4938
0.0007 6.0016 1.0038 -0.0220 -0.8235 0.4938
3.9987 -0.0096 2.9882 -0.0385 0.7949 0.7877
-2.9996 -4.9942 -2.9943 0.0601 0.0931 -1.0000
-0.0003 -1.9904 -6.9992 -1.0219 0.0268 -0.3530
2.9995 3.9983 -0.0055 -0.4938 -0.0611 0.8376
-1.9994 -1.0040 4.0036 0.8978 -0.0497 -0.3160
0.0003 1.9904 6.9992 1.0219 -0.0268 0.3530
1.9998 3.9905 5.9954 0.5579 -0.0091 0.8314

_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.228
_diffrn_reflns_theta_min         4.630
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00   7.00   1.00    1.00    --  -41.68 114.00-120.00   98
  2  ω     14.00  91.00   1.00    1.00    --   41.68-114.00 148.00   77
  3  ω     33.00 117.00   1.00    1.00    --  109.13-114.00 148.00   84
  4  ω    100.00 178.00   1.00    1.00    --  109.13 114.00-120.00   78
  5  ω    -50.00  33.00   1.00    1.00    --  -41.68  38.00-120.00   83
  6  ω    -50.00  33.00   1.00    1.00    --  -41.68  38.00 120.00   83
  7  ω   -122.00  -1.00   1.00    1.00    --  -41.68 -19.00 -60.00  121
  8  ω     23.00  98.00   1.00    1.00    --   41.68-125.00   0.00   75
  9  ω     36.00 121.00   1.00    1.00    --  109.13-125.00  30.00   85
 10  ω     26.00 109.00   1.00    1.00    --  109.13 -94.00  60.00   83
 11  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00-180.00   58
 12  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -60.00   98
 13  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00   0.00   58
 14  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00 120.00   62
 15  ω     94.00 178.00   1.00    1.00    --  109.13 125.00   0.00   84
 16  ω     26.00 109.00   1.00    1.00    --  109.13 -94.00-120.00   83
 17  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00 -30.00   62
 18  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00-120.00   62
 19  ω     26.00 109.00   1.00    1.00    --  109.13 -94.00-180.00   83
 20  ω     81.00 178.00   1.00    1.00    --  109.13  30.00 120.00   97
 21  ω     81.00 178.00   1.00    1.00    --  109.13  30.00-180.00   97
 22  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
 23  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00   0.00  109
 24  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00 -90.00  109
 25  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00 120.00  109
 26  ω    -50.00  33.00   1.00    1.00    --  -41.68  38.00  30.00   83
 27  ω     14.00 115.00   1.00    1.00    --   41.68  57.00  90.00  101
 28  ω     81.00 178.00   1.00    1.00    --  109.13  30.00  30.00   97
 29  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 120.00   98
 30  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -90.00   98
 31  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -30.00   98
 32  ω     80.00 178.00   1.00    1.00    --  109.13  61.00-150.00   98
 33  ω     83.00 178.00   1.00    1.00    --  109.13  45.00  60.00   95
 34  ω     83.00 178.00   1.00    1.00    --  109.13  45.00  30.00   95
 35  ω     80.00 178.00   1.00    1.00    --  109.13  61.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1250753000
_diffrn_orient_matrix_UB_12      -0.0294669000
_diffrn_orient_matrix_UB_13      0.1543896000
_diffrn_orient_matrix_UB_21      0.1708443000
_diffrn_orient_matrix_UB_22      -0.1434049000
_diffrn_orient_matrix_UB_23      0.0369440000
_diffrn_orient_matrix_UB_31      0.1759689000
_diffrn_orient_matrix_UB_32      0.0775148000
_diffrn_orient_matrix_UB_33      0.0283894000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             2195
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.021
_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)+(0.1256P)²+0.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2046
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3357(4) 0.2051(2) 0.5933(2) 0.0391(6) Uani 1 1 d . . . . .
O2 O 0.2850(3) 0.8309(2) -0.0112(2) 0.0367(5) Uani 1 1 d . . . . .
O3 O -0.0392(3) 0.72934(19) 0.01816(19) 0.0299(5) Uani 1 1 d . . . . .
N1 N 0.6966(4) 0.1735(3) 0.4568(3) 0.0345(6) Uani 1 1 d . . . . .
C1 C 0.4871(5) 0.2430(3) 0.4707(3) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.7153(6) 0.0644(3) 0.5943(3) 0.0457(8) Uani 1 1 d . . . . .
H2A H 0.8330 0.0836 0.6389 0.055 Uiso 1 1 calc R . . . .
H2B H 0.7647 -0.0335 0.5830 0.055 Uiso 1 1 calc R . . . .
C3 C 0.4629(6) 0.0798(3) 0.6826(3) 0.0435(8) Uani 1 1 d . . . . .
H3A H 0.3885 -0.0067 0.7024 0.052 Uiso 1 1 calc R . . . .
H3B H 0.4665 0.0961 0.7723 0.052 Uiso 1 1 calc R . . . .
C4 C 0.3955(4) 0.3688(3) 0.3630(3) 0.0235(6) Uani 1 1 d . . . . .
C5 C 0.1662(4) 0.3885(3) 0.2978(3) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.0550 0.3167 0.3247 0.030 Uiso 1 1 calc R . . . .
C6 C 0.0941(4) 0.5450(3) 0.3090(3) 0.0255(6) Uani 1 1 d . . . . .
H6 H -0.0711 0.5893 0.3437 0.031 Uiso 1 1 calc R . . . .
C7 C 0.3183(4) 0.5274(3) 0.3749(3) 0.0262(6) Uani 1 1 d . . . . .
H7 H 0.3181 0.5577 0.4588 0.031 Uiso 1 1 calc R . . . .
C8 C 0.5418(4) 0.4256(3) 0.2144(3) 0.0246(6) Uani 1 1 d . . . . .
H8 H 0.7067 0.3813 0.1791 0.030 Uiso 1 1 calc R . . . .
C9 C 0.3158(4) 0.4442(3) 0.1479(3) 0.0238(6) Uani 1 1 d . . . . .
H9 H 0.3144 0.4142 0.0640 0.029 Uiso 1 1 calc R . . . .
C10 C 0.2451(4) 0.6029(3) 0.1600(3) 0.0225(5) Uani 1 1 d . . . . .
C11 C 0.4703(4) 0.5830(3) 0.2262(3) 0.0243(6) Uani 1 1 d . . . . .
H11 H 0.5821 0.6544 0.2002 0.029 Uiso 1 1 calc R . . . .
C12 C 0.1713(4) 0.7324(3) 0.0480(3) 0.0247(5) Uani 1 1 d . . . . .
C13 C -0.1209(5) 0.8535(3) -0.0913(3) 0.0310(6) Uani 1 1 d . . . . .
H13A H -0.0086 0.8565 -0.1797 0.046 Uiso 1 1 calc GR . . . .
H13B H -0.1296 0.9414 -0.0657 0.046 Uiso 1 1 calc GR . . . .
H13C H -0.2796 0.8461 -0.1024 0.046 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
O1 C1 1.347(3) . ?
O1 C3 1.456(3) . ?
O2 C12 1.216(3) . ?
O3 C12 1.343(3) . ?
O3 C13 1.453(3) . ?
N1 C1 1.265(3) . ?
N1 C2 1.486(4) . ?
C1 C4 1.471(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.538(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.580(3) . ?
C4 C7 1.579(4) . ?
C4 C8 1.552(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.554(4) . ?
C5 C9 1.567(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.562(3) . ?
C6 C10 1.568(3) . ?
C7 H7 1.0000 . ?
C7 C11 1.564(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.573(3) . ?
C8 C11 1.566(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.579(3) . ?
C10 C11 1.565(3) . ?
C10 C12 1.482(3) . ?
C11 H11 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 O1 C3 106.6(2) . . ?
C12 O3 C13 114.53(19) . . ?
C1 N1 C2 105.8(2) . . ?
O1 C1 C4 116.2(2) . . ?
N1 C1 O1 119.3(2) . . ?
N1 C1 C4 124.5(2) . . ?
N1 C2 H2A 110.7 . . ?
N1 C2 H2B 110.7 . . ?
N1 C2 C3 105.0(2) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
O1 C3 C2 102.9(2) . . ?
O1 C3 H3A 111.2 . . ?
O1 C3 H3B 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C1 C4 C5 127.1(2) . . ?
C1 C4 C7 125.8(2) . . ?
C1 C4 C8 123.4(2) . . ?
C7 C4 C5 89.04(17) . . ?
C8 C4 C5 90.23(18) . . ?
C8 C4 C7 90.12(18) . . ?
C4 C5 H5 125.3 . . ?
C6 C5 C4 90.29(19) . . ?
C6 C5 H5 125.3 . . ?
C6 C5 C9 90.20(18) . . ?
C9 C5 C4 89.49(18) . . ?
C9 C5 H5 125.3 . . ?
C5 C6 H6 125.1 . . ?
C5 C6 C7 90.60(18) . . ?
C5 C6 C10 90.71(18) . . ?
C7 C6 H6 125.1 . . ?
C7 C6 C10 89.34(18) . . ?
C10 C6 H6 125.1 . . ?
C4 C7 H7 125.2 . . ?
C6 C7 C4 90.07(18) . . ?
C6 C7 H7 125.2 . . ?
C6 C7 C11 90.76(18) . . ?
C11 C7 C4 89.41(18) . . ?
C11 C7 H7 125.2 . . ?
C4 C8 H8 125.0 . . ?
C4 C8 C9 90.32(18) . . ?
C4 C8 C11 90.32(18) . . ?
C9 C8 H8 125.0 . . ?
C11 C8 H8 125.0 . . ?
C11 C8 C9 90.63(17) . . ?
C5 C9 C8 89.95(18) . . ?
C5 C9 H9 125.5 . . ?
C5 C9 C10 89.82(17) . . ?
C8 C9 H9 125.5 . . ?
C8 C9 C10 89.09(18) . . ?
C10 C9 H9 125.5 . . ?
C6 C10 C9 89.26(18) . . ?
C11 C10 C6 90.50(17) . . ?
C11 C10 C9 90.43(17) . . ?
C12 C10 C6 126.5(2) . . ?
C12 C10 C9 125.7(2) . . ?
C12 C10 C11 123.4(2) . . ?
C7 C11 C8 90.14(18) . . ?
C7 C11 C10 89.38(18) . . ?
C7 C11 H11 125.4 . . ?
C8 C11 H11 125.4 . . ?
C10 C11 C8 89.86(18) . . ?
C10 C11 H11 125.4 . . ?
O2 C12 O3 123.0(2) . . ?
O2 C12 C10 125.0(2) . . ?
O3 C12 C10 111.9(2) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C1 C4 C5 -58.1(3) . . . . ?
O1 C1 C4 C7 63.1(3) . . . . ?
O1 C1 C4 C8 -178.3(2) . . . . ?
N1 C1 C4 C5 124.4(3) . . . . ?
N1 C1 C4 C7 -114.4(3) . . . . ?
N1 C1 C4 C8 4.1(4) . . . . ?
N1 C2 C3 O1 -6.3(3) . . . . ?
C1 O1 C3 C2 5.2(3) . . . . ?
C1 N1 C2 C3 5.2(3) . . . . ?
C1 C4 C5 C6 136.5(3) . . . . ?
C1 C4 C5 C9 -133.3(3) . . . . ?
C1 C4 C7 C6 -137.4(2) . . . . ?
C1 C4 C7 C11 131.8(2) . . . . ?
C1 C4 C8 C9 135.9(2) . . . . ?
C1 C4 C8 C11 -133.5(2) . . . . ?
C2 N1 C1 O1 -2.0(4) . . . . ?
C2 N1 C1 C4 175.5(3) . . . . ?
C3 O1 C1 N1 -2.3(4) . . . . ?
C3 O1 C1 C4 180.0(2) . . . . ?
C4 C5 C6 C7 -0.49(18) . . . . ?
C4 C5 C6 C10 88.86(18) . . . . ?
C4 C5 C9 C8 -0.57(18) . . . . ?
C4 C5 C9 C10 -89.65(18) . . . . ?
C4 C7 C11 C8 1.01(18) . . . . ?
C4 C7 C11 C10 90.86(18) . . . . ?
C4 C8 C9 C5 0.58(18) . . . . ?
C4 C8 C9 C10 90.40(18) . . . . ?
C4 C8 C11 C7 -1.02(18) . . . . ?
C4 C8 C11 C10 -90.40(18) . . . . ?
C5 C4 C7 C6 -0.48(18) . . . . ?
C5 C4 C7 C11 -91.25(18) . . . . ?
C5 C4 C8 C9 -0.57(18) . . . . ?
C5 C4 C8 C11 90.05(18) . . . . ?
C5 C6 C7 C4 0.49(18) . . . . ?
C5 C6 C7 C11 89.90(18) . . . . ?
C5 C6 C10 C9 0.63(17) . . . . ?
C5 C6 C10 C11 -89.79(18) . . . . ?
C5 C6 C10 C12 136.4(3) . . . . ?
C5 C9 C10 C6 -0.62(17) . . . . ?
C5 C9 C10 C11 89.88(18) . . . . ?
C5 C9 C10 C12 -136.9(2) . . . . ?
C6 C5 C9 C8 89.72(18) . . . . ?
C6 C5 C9 C10 0.63(17) . . . . ?
C6 C7 C11 C8 -89.06(18) . . . . ?
C6 C7 C11 C10 0.80(18) . . . . ?
C6 C10 C11 C7 -0.80(18) . . . . ?
C6 C10 C11 C8 89.34(18) . . . . ?
C6 C10 C12 O2 125.9(3) . . . . ?
C6 C10 C12 O3 -54.2(3) . . . . ?
C7 C4 C5 C6 0.49(18) . . . . ?
C7 C4 C5 C9 90.69(18) . . . . ?
C7 C4 C8 C9 -89.62(18) . . . . ?
C7 C4 C8 C11 1.01(18) . . . . ?
C7 C6 C10 C9 91.22(18) . . . . ?
C7 C6 C10 C11 0.80(18) . . . . ?
C7 C6 C10 C12 -133.0(3) . . . . ?
C8 C4 C5 C6 -89.63(18) . . . . ?
C8 C4 C5 C9 0.58(18) . . . . ?
C8 C4 C7 C6 89.75(18) . . . . ?
C8 C4 C7 C11 -1.01(18) . . . . ?
C8 C9 C10 C6 -90.58(17) . . . . ?
C8 C9 C10 C11 -0.08(17) . . . . ?
C8 C9 C10 C12 133.1(2) . . . . ?
C9 C5 C6 C7 -89.99(18) . . . . ?
C9 C5 C6 C10 -0.63(17) . . . . ?
C9 C8 C11 C7 89.30(18) . . . . ?
C9 C8 C11 C10 -0.08(17) . . . . ?
C9 C10 C11 C7 -90.07(18) . . . . ?
C9 C10 C11 C8 0.08(17) . . . . ?
C9 C10 C12 O2 -113.3(3) . . . . ?
C9 C10 C12 O3 66.6(3) . . . . ?
C10 C6 C7 C4 -90.21(18) . . . . ?
C10 C6 C7 C11 -0.80(18) . . . . ?
C11 C8 C9 C5 -89.74(18) . . . . ?
C11 C8 C9 C10 0.08(17) . . . . ?
C11 C10 C12 O2 5.8(4) . . . . ?
C11 C10 C12 O3 -174.3(2) . . . . ?
C12 C10 C11 C7 135.1(2) . . . . ?
C12 C10 C11 C8 -134.8(2) . . . . ?
C13 O3 C12 O2 0.1(4) . . . . ?
C13 O3 C12 C10 -179.8(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.222
_oxdiff_exptl_absorpt_empirical_full_min 0.613

####################################################################### 
# 
# 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_rh062
_database_code_depnum_ccdc_archive 'CCDC 1854643'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_date             2015-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H22 Cl N O6'
_chemical_formula_sum            'C24 H22 Cl N O6'
_chemical_formula_weight         455.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H22 Cl N O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.33701(10)
_cell_length_b                   17.9259(3)
_cell_length_c                   21.5579(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.9404(17)
_cell_angle_gamma                90
_cell_volume                     2059.74(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11255
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.1660
_cell_measurement_theta_min      3.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 11 -5 0.1161
0 -11 5 0.0096
3 -4 -6 0.0406
-3 0 8 0.1574
0 0 14 0.0364
0 0 -14 0.0010

_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0008 11.0017 -4.9923 0.0161 -0.8571 0.5357
0.0008 -11.0017 4.9923 -0.0161 0.8571 -0.5357
2.9994 -4.0045 -6.0008 -0.0089 0.6821 0.7416
-2.9991 0.0038 7.9980 0.0137 -0.3695 -0.9438
0.0013 -0.0037 13.9986 0.8161 0.0731 -0.5770
-0.0013 0.0037 -13.9986 -0.8161 -0.0731 0.5770

_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.465
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  24.00   1.00    1.00    --  -41.80  96.00 164.00  105
  2  ω     -2.00  81.00   1.00    1.00    --   41.80 -96.00  56.00   83
  3  ω    101.00 178.00   1.00    1.00    --  109.13  96.00 164.00   77
  4  ω     27.00 110.00   1.00    1.00    --  109.13 -96.00  56.00   83
  5  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00  60.00  100
  6  ω    -50.00  32.00   1.00    1.00    --  -41.80  38.00 -60.00   82
  7  ω    -50.00  32.00   1.00    1.00    --  -41.80  38.00-150.00   82
  8  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00 -90.00   58
  9  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00-180.00   58
 10  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00 120.00   58
 11  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00  60.00   62
 12  ω     36.00 121.00   1.00    1.00    --  109.13-125.00-180.00   85
 13  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00-120.00   62
 14  ω     36.00  98.00   1.00    1.00    --  109.13 -45.00  90.00   62
 15  ω     33.00  91.00   1.00    1.00    --  109.13 -30.00   0.00   58
 16  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -60.00  100
 17  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00 -90.00  109
 18  ω   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00-180.00  100
 19  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00 150.00  109
 20  ω     77.00 178.00   1.00    1.00    --  109.13  77.00-120.00  101
 21  ω     81.00 178.00   1.00    1.00    --  109.13  30.00-120.00   97
 22  ω     56.00 178.00   1.00    1.00    --  109.13  15.00 150.00  122
 23  ω     83.00 178.00   1.00    1.00    --  109.13  45.00-180.00   95
 24  ω     56.00 178.00   1.00    1.00    --  109.13  15.00   0.00  122
 25  ω     80.00 178.00   1.00    1.00    --  109.13  61.00   0.00   98
 26  ω     26.00 109.00   1.00    1.00    --  109.13 -94.00-120.00   83
 27  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  30.00  101
 28  ω    -96.00  -2.00   1.00    1.00    --  -41.80 125.00 -30.00   94
 29  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 -90.00   99
 30  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00  30.00  109
 31  ω      9.00 118.00   1.00    1.00    --   41.80  77.00 -60.00  109
 32  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 120.00  101
 33  ω     80.00 178.00   1.00    1.00    --  109.13  61.00 -30.00   98
 34  ω     26.00 109.00   1.00    1.00    --  109.13 -94.00 -30.00   83
 35  ω     77.00 178.00   1.00    1.00    --  109.13  77.00 -90.00  101
 36  ω     80.00 105.00   1.00    1.00    --  109.13  61.00-180.00   25
 37  ω     77.00 178.00   1.00    1.00    --  109.13  77.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1509264000
_diffrn_orient_matrix_UB_12      0.0279252000
_diffrn_orient_matrix_UB_13      0.0582892000
_diffrn_orient_matrix_UB_21      0.1369467000
_diffrn_orient_matrix_UB_22      -0.0755389000
_diffrn_orient_matrix_UB_23      0.0051874000
_diffrn_orient_matrix_UB_31      0.2047933000
_diffrn_orient_matrix_UB_32      0.0299961000
_diffrn_orient_matrix_UB_33      -0.0412316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3338
_reflns_number_total             4238
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.021
_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)+(0.0875P)²+0.8499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16938(11) 0.60021(3) 0.49959(3) 0.02324(17) Uani 1 1 d . . . . .
O1 O 0.3419(3) 0.77050(9) 0.60843(7) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.0198(3) 1.00020(10) 0.35941(8) 0.0287(4) Uani 1 1 d . . . . .
O3 O -0.3377(3) 0.93431(9) 0.34718(8) 0.0252(4) Uani 1 1 d . . . . .
O4 O -0.1449(3) 0.62966(9) 0.67781(8) 0.0218(4) Uani 1 1 d . . . . .
O5 O 0.5594(3) 0.84034(9) 0.90250(8) 0.0241(4) Uani 1 1 d . . . . .
O6 O 0.4649(4) 0.93153(9) 0.83401(8) 0.0302(4) Uani 1 1 d . . . . .
N1 N -0.0337(3) 0.70926(10) 0.60210(8) 0.0158(4) Uani 1 1 d . . . . .
C1 C -0.1175(4) 0.59380(12) 0.53965(11) 0.0194(5) Uani 1 1 d . . . . .
H1A H -0.2480 0.5694 0.5124 0.023 Uiso 1 1 calc R . . . .
H1B H -0.0895 0.5628 0.5774 0.023 Uiso 1 1 calc R . . . .
C2 C -0.2070(4) 0.67051(12) 0.55784(10) 0.0170(5) Uani 1 1 d . . . . .
H2A H -0.2311 0.7014 0.5199 0.020 Uiso 1 1 calc R . . . .
H2B H -0.3720 0.6656 0.5764 0.020 Uiso 1 1 calc R . . . .
C3 C 0.1362(4) 0.76236(12) 0.58190(10) 0.0155(4) Uani 1 1 d . . . . .
C4 C 0.0558(4) 0.80964(12) 0.52786(10) 0.0156(4) Uani 1 1 d . . . . .
C5 C 0.1517(4) 0.89208(12) 0.52051(11) 0.0166(4) Uani 1 1 d . . . . .
H5 H 0.2634 0.9193 0.5515 0.020 Uiso 1 1 calc R . . . .
C6 C -0.1214(4) 0.91624(12) 0.49884(10) 0.0181(5) Uani 1 1 d . . . . .
H6 H -0.2099 0.9616 0.5135 0.022 Uiso 1 1 calc R . . . .
C7 C -0.2156(4) 0.83425(12) 0.50532(10) 0.0173(5) Uani 1 1 d . . . . .
H7 H -0.3735 0.8190 0.5250 0.021 Uiso 1 1 calc R . . . .
C8 C 0.1208(4) 0.79402(12) 0.45826(10) 0.0171(5) Uani 1 1 d . . . . .
H8 H 0.2105 0.7489 0.4434 0.021 Uiso 1 1 calc R . . . .
C9 C 0.2124(4) 0.87661(12) 0.45178(10) 0.0178(5) Uani 1 1 d . . . . .
H9 H 0.3696 0.8922 0.4321 0.021 Uiso 1 1 calc R . . . .
C10 C -0.0580(4) 0.89992(12) 0.42894(10) 0.0172(5) Uani 1 1 d . . . . .
C11 C -0.1525(4) 0.81796(12) 0.43641(10) 0.0183(5) Uani 1 1 d . . . . .
H11 H -0.2636 0.7905 0.4054 0.022 Uiso 1 1 calc R . . . .
C12 C -0.1149(4) 0.95064(12) 0.37539(11) 0.0186(5) Uani 1 1 d . . . . .
C13 C -0.4130(5) 0.98082(15) 0.29449(12) 0.0312(6) Uani 1 1 d . . . . .
H13A H -0.2954 0.9739 0.2615 0.047 Uiso 1 1 calc GR . . . .
H13B H -0.4121 1.0333 0.3073 0.047 Uiso 1 1 calc GR . . . .
H13C H -0.5823 0.9668 0.2790 0.047 Uiso 1 1 calc GR . . . .
C14 C -0.0331(4) 0.68616(12) 0.66406(10) 0.0164(4) Uani 1 1 d . . . . .
C15 C 0.0931(4) 0.73454(12) 0.71258(10) 0.0165(5) Uani 1 1 d . . . . .
C16 C 0.0168(4) 0.73638(13) 0.78170(11) 0.0196(5) Uani 1 1 d . . . . .
H16 H -0.1284 0.7089 0.7984 0.023 Uiso 1 1 calc R . . . .
C17 C 0.0504(4) 0.82318(13) 0.78243(11) 0.0193(5) Uani 1 1 d . . . . .
H17 H -0.0692 0.8595 0.8000 0.023 Uiso 1 1 calc R . . . .
C18 C 0.1272(4) 0.82182(12) 0.71354(10) 0.0166(5) Uani 1 1 d . . . . .
H18 H 0.0643 0.8568 0.6802 0.020 Uiso 1 1 calc R . . . .
C19 C 0.3756(4) 0.72446(12) 0.73605(10) 0.0174(5) Uani 1 1 d . . . . .
H19 H 0.4954 0.6880 0.7188 0.021 Uiso 1 1 calc R . . . .
C20 C 0.2983(4) 0.72657(13) 0.80503(10) 0.0197(5) Uani 1 1 d . . . . .
H20 H 0.3606 0.6917 0.8386 0.024 Uiso 1 1 calc R . . . .
C21 C 0.3335(4) 0.81300(13) 0.80553(11) 0.0190(5) Uani 1 1 d . . . . .
C22 C 0.4090(4) 0.81119(12) 0.73598(10) 0.0171(5) Uani 1 1 d . . . . .
H22 H 0.5541 0.8385 0.7191 0.021 Uiso 1 1 calc R . . . .
C23 C 0.4645(4) 0.86050(13) 0.85350(11) 0.0189(5) Uani 1 1 d . . . . .
C24 C 0.5934(6) 0.98427(14) 0.87503(13) 0.0320(6) Uani 1 1 d . . . . .
H24A H 0.5848 1.0341 0.8563 0.048 Uiso 1 1 calc GR . . . .
H24B H 0.7694 0.9694 0.8817 0.048 Uiso 1 1 calc GR . . . .
H24C H 0.5133 0.9852 0.9149 0.048 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 1.800(3) . ?
O1 C3 1.220(3) . ?
O2 C12 1.204(3) . ?
O3 C12 1.340(3) . ?
O3 C13 1.449(3) . ?
O4 C14 1.220(3) . ?
O5 C23 1.203(3) . ?
O6 C23 1.341(3) . ?
O6 C24 1.444(3) . ?
N1 C2 1.469(3) . ?
N1 C3 1.399(3) . ?
N1 C14 1.398(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.486(3) . ?
C4 C5 1.575(3) . ?
C4 C7 1.568(3) . ?
C4 C8 1.582(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.568(3) . ?
C5 C9 1.558(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.562(3) . ?
C6 C10 1.588(3) . ?
C7 H7 1.0000 . ?
C7 C11 1.567(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.568(3) . ?
C8 C11 1.569(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.558(3) . ?
C10 C11 1.564(3) . ?
C10 C12 1.488(3) . ?
C11 H11 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.493(3) . ?
C15 C16 1.565(3) . ?
C15 C18 1.575(3) . ?
C15 C19 1.576(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.566(3) . ?
C16 C20 1.570(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.561(3) . ?
C17 C21 1.577(3) . ?
C18 H18 1.0000 . ?
C18 C22 1.568(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.564(3) . ?
C19 C22 1.565(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.561(3) . ?
C21 C22 1.573(3) . ?
C21 C23 1.486(3) . ?
C22 H22 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 O3 C13 115.73(19) . . ?
C23 O6 C24 116.00(19) . . ?
C3 N1 C2 121.06(18) . . ?
C14 N1 C2 116.80(18) . . ?
C14 N1 C3 121.94(18) . . ?
Cl1 C1 H1A 109.5 . . ?
Cl1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 Cl1 110.73(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
N1 C2 C1 113.65(18) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 N1 121.1(2) . . ?
O1 C3 C4 121.1(2) . . ?
N1 C3 C4 117.80(19) . . ?
C3 C4 C5 122.14(18) . . ?
C3 C4 C7 128.9(2) . . ?
C3 C4 C8 125.03(18) . . ?
C5 C4 C8 89.00(16) . . ?
C7 C4 C5 90.27(16) . . ?
C7 C4 C8 90.00(16) . . ?
C4 C5 H5 125.2 . . ?
C6 C5 C4 89.27(16) . . ?
C6 C5 H5 125.2 . . ?
C9 C5 C4 90.75(16) . . ?
C9 C5 H5 125.2 . . ?
C9 C5 C6 90.08(16) . . ?
C5 C6 H6 125.3 . . ?
C5 C6 C10 89.53(17) . . ?
C7 C6 C5 90.70(16) . . ?
C7 C6 H6 125.3 . . ?
C7 C6 C10 89.81(16) . . ?
C10 C6 H6 125.3 . . ?
C4 C7 H7 125.2 . . ?
C6 C7 C4 89.75(16) . . ?
C6 C7 H7 125.2 . . ?
C6 C7 C11 90.27(16) . . ?
C11 C7 C4 90.06(17) . . ?
C11 C7 H7 125.2 . . ?
C4 C8 H8 125.3 . . ?
C9 C8 C4 90.11(16) . . ?
C9 C8 H8 125.3 . . ?
C9 C8 C11 90.24(16) . . ?
C11 C8 C4 89.46(17) . . ?
C11 C8 H8 125.3 . . ?
C5 C9 C8 90.14(16) . . ?
C5 C9 H9 125.1 . . ?
C5 C9 C10 91.05(17) . . ?
C8 C9 H9 125.1 . . ?
C10 C9 C8 89.63(16) . . ?
C10 C9 H9 125.1 . . ?
C9 C10 C6 89.34(16) . . ?
C9 C10 C11 90.78(16) . . ?
C11 C10 C6 89.42(16) . . ?
C12 C10 C6 125.34(19) . . ?
C12 C10 C9 123.9(2) . . ?
C12 C10 C11 126.85(19) . . ?
C7 C11 C8 90.47(16) . . ?
C7 C11 H11 125.2 . . ?
C8 C11 H11 125.2 . . ?
C10 C11 C7 90.50(16) . . ?
C10 C11 C8 89.33(17) . . ?
C10 C11 H11 125.2 . . ?
O2 C12 O3 124.1(2) . . ?
O2 C12 C10 124.9(2) . . ?
O3 C12 C10 111.06(19) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 N1 120.1(2) . . ?
O4 C14 C15 121.4(2) . . ?
N1 C14 C15 118.44(19) . . ?
C14 C15 C16 123.33(19) . . ?
C14 C15 C18 129.35(18) . . ?
C14 C15 C19 123.24(19) . . ?
C16 C15 C18 90.13(16) . . ?
C16 C15 C19 89.32(16) . . ?
C18 C15 C19 90.09(16) . . ?
C15 C16 H16 125.2 . . ?
C15 C16 C17 89.72(17) . . ?
C15 C16 C20 90.64(17) . . ?
C17 C16 H16 125.2 . . ?
C17 C16 C20 90.04(17) . . ?
C20 C16 H16 125.2 . . ?
C16 C17 H17 125.1 . . ?
C16 C17 C21 89.75(17) . . ?
C18 C17 C16 90.60(16) . . ?
C18 C17 H17 125.1 . . ?
C18 C17 C21 90.27(17) . . ?
C21 C17 H17 125.1 . . ?
C15 C18 H18 125.4 . . ?
C17 C18 C15 89.55(16) . . ?
C17 C18 H18 125.4 . . ?
C17 C18 C22 90.16(16) . . ?
C22 C18 C15 89.53(16) . . ?
C22 C18 H18 125.4 . . ?
C15 C19 H19 125.1 . . ?
C20 C19 C15 90.44(17) . . ?
C20 C19 H19 125.1 . . ?
C20 C19 C22 90.71(16) . . ?
C22 C19 C15 89.59(16) . . ?
C22 C19 H19 125.1 . . ?
C16 C20 H20 125.4 . . ?
C19 C20 C16 89.60(16) . . ?
C19 C20 H20 125.4 . . ?
C21 C20 C16 90.22(17) . . ?
C21 C20 C19 89.61(17) . . ?
C21 C20 H20 125.4 . . ?
C20 C21 C17 89.99(17) . . ?
C20 C21 C22 90.55(17) . . ?
C22 C21 C17 89.40(16) . . ?
C23 C21 C17 124.2(2) . . ?
C23 C21 C20 128.73(19) . . ?
C23 C21 C22 122.7(2) . . ?
C18 C22 C21 90.17(17) . . ?
C18 C22 H22 125.2 . . ?
C19 C22 C18 90.78(16) . . ?
C19 C22 C21 89.13(16) . . ?
C19 C22 H22 125.2 . . ?
C21 C22 H22 125.2 . . ?
O5 C23 O6 123.6(2) . . ?
O5 C23 C21 126.9(2) . . ?
O6 C23 C21 109.53(19) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 N1 -63.4(2) . . . . ?
O1 C3 C4 C5 -29.9(3) . . . . ?
O1 C3 C4 C7 -150.9(2) . . . . ?
O1 C3 C4 C8 84.6(3) . . . . ?
O4 C14 C15 C16 -23.4(3) . . . . ?
O4 C14 C15 C18 -146.3(2) . . . . ?
O4 C14 C15 C19 91.0(3) . . . . ?
N1 C3 C4 C5 148.8(2) . . . . ?
N1 C3 C4 C7 27.8(3) . . . . ?
N1 C3 C4 C8 -96.7(3) . . . . ?
N1 C14 C15 C16 152.8(2) . . . . ?
N1 C14 C15 C18 30.0(3) . . . . ?
N1 C14 C15 C19 -92.7(3) . . . . ?
C2 N1 C3 O1 -147.1(2) . . . . ?
C2 N1 C3 C4 34.2(3) . . . . ?
C2 N1 C14 O4 10.3(3) . . . . ?
C2 N1 C14 C15 -166.05(19) . . . . ?
C3 N1 C2 C1 98.2(2) . . . . ?
C3 N1 C14 O4 -164.6(2) . . . . ?
C3 N1 C14 C15 19.1(3) . . . . ?
C3 C4 C5 C6 -137.5(2) . . . . ?
C3 C4 C5 C9 132.5(2) . . . . ?
C3 C4 C7 C6 132.8(2) . . . . ?
C3 C4 C7 C11 -137.0(2) . . . . ?
C3 C4 C8 C9 -130.2(2) . . . . ?
C3 C4 C8 C11 139.5(2) . . . . ?
C4 C5 C6 C7 -0.69(17) . . . . ?
C4 C5 C6 C10 -90.49(16) . . . . ?
C4 C5 C9 C8 -0.62(16) . . . . ?
C4 C5 C9 C10 89.01(16) . . . . ?
C4 C7 C11 C8 -0.58(16) . . . . ?
C4 C7 C11 C10 -89.92(16) . . . . ?
C4 C8 C9 C5 0.62(16) . . . . ?
C4 C8 C9 C10 -90.43(16) . . . . ?
C4 C8 C11 C7 0.58(16) . . . . ?
C4 C8 C11 C10 91.08(16) . . . . ?
C5 C4 C7 C6 -0.69(17) . . . . ?
C5 C4 C7 C11 89.58(16) . . . . ?
C5 C4 C8 C9 -0.61(16) . . . . ?
C5 C4 C8 C11 -90.85(16) . . . . ?
C5 C6 C7 C4 0.69(17) . . . . ?
C5 C6 C7 C11 -89.37(17) . . . . ?
C5 C6 C10 C9 -0.25(16) . . . . ?
C5 C6 C10 C11 90.54(16) . . . . ?
C5 C6 C10 C12 -132.7(2) . . . . ?
C5 C9 C10 C6 0.26(16) . . . . ?
C5 C9 C10 C11 -89.15(17) . . . . ?
C5 C9 C10 C12 133.8(2) . . . . ?
C6 C5 C9 C8 -89.89(16) . . . . ?
C6 C5 C9 C10 -0.26(16) . . . . ?
C6 C7 C11 C8 89.17(16) . . . . ?
C6 C7 C11 C10 -0.17(16) . . . . ?
C6 C10 C11 C7 0.16(16) . . . . ?
C6 C10 C11 C8 -90.30(17) . . . . ?
C6 C10 C12 O2 86.9(3) . . . . ?
C6 C10 C12 O3 -92.7(3) . . . . ?
C7 C4 C5 C6 0.68(17) . . . . ?
C7 C4 C5 C9 -89.38(17) . . . . ?
C7 C4 C8 C9 89.66(16) . . . . ?
C7 C4 C8 C11 -0.58(16) . . . . ?
C7 C6 C10 C9 -90.96(16) . . . . ?
C7 C6 C10 C11 -0.17(16) . . . . ?
C7 C6 C10 C12 136.6(2) . . . . ?
C8 C4 C5 C6 90.68(16) . . . . ?
C8 C4 C5 C9 0.61(16) . . . . ?
C8 C4 C7 C6 -89.69(16) . . . . ?
C8 C4 C7 C11 0.58(16) . . . . ?
C8 C9 C10 C6 90.38(16) . . . . ?
C8 C9 C10 C11 0.98(17) . . . . ?
C8 C9 C10 C12 -136.1(2) . . . . ?
C9 C5 C6 C7 90.06(17) . . . . ?
C9 C5 C6 C10 0.25(16) . . . . ?
C9 C8 C11 C7 -89.53(16) . . . . ?
C9 C8 C11 C10 0.97(17) . . . . ?
C9 C10 C11 C7 89.49(17) . . . . ?
C9 C10 C11 C8 -0.98(17) . . . . ?
C9 C10 C12 O2 -30.4(4) . . . . ?
C9 C10 C12 O3 150.0(2) . . . . ?
C10 C6 C7 C4 90.22(16) . . . . ?
C10 C6 C7 C11 0.17(16) . . . . ?
C11 C8 C9 C5 90.08(17) . . . . ?
C11 C8 C9 C10 -0.97(17) . . . . ?
C11 C10 C12 O2 -152.0(2) . . . . ?
C11 C10 C12 O3 28.4(3) . . . . ?
C12 C10 C11 C7 -135.5(2) . . . . ?
C12 C10 C11 C8 134.0(2) . . . . ?
C13 O3 C12 O2 -0.1(3) . . . . ?
C13 O3 C12 C10 179.5(2) . . . . ?
C14 N1 C2 C1 -76.7(3) . . . . ?
C14 N1 C3 O1 27.6(3) . . . . ?
C14 N1 C3 C4 -151.2(2) . . . . ?
C14 C15 C16 C17 -139.4(2) . . . . ?
C14 C15 C16 C20 130.6(2) . . . . ?
C14 C15 C18 C17 135.3(2) . . . . ?
C14 C15 C18 C22 -134.5(2) . . . . ?
C14 C15 C19 C20 -130.6(2) . . . . ?
C14 C15 C19 C22 138.7(2) . . . . ?
C15 C16 C17 C18 -0.11(16) . . . . ?
C15 C16 C17 C21 -90.37(17) . . . . ?
C15 C16 C20 C19 -0.15(17) . . . . ?
C15 C16 C20 C21 89.45(17) . . . . ?
C15 C18 C22 C19 -0.74(16) . . . . ?
C15 C18 C22 C21 -89.87(16) . . . . ?
C15 C19 C20 C16 0.15(16) . . . . ?
C15 C19 C20 C21 -90.07(16) . . . . ?
C15 C19 C22 C18 0.74(16) . . . . ?
C15 C19 C22 C21 90.90(16) . . . . ?
C16 C15 C18 C17 -0.10(16) . . . . ?
C16 C15 C18 C22 90.06(16) . . . . ?
C16 C15 C19 C20 -0.15(16) . . . . ?
C16 C15 C19 C22 -90.86(16) . . . . ?
C16 C17 C18 C15 0.10(16) . . . . ?
C16 C17 C18 C22 -89.43(16) . . . . ?
C16 C17 C21 C20 -0.27(17) . . . . ?
C16 C17 C21 C22 90.28(17) . . . . ?
C16 C17 C21 C23 -139.4(2) . . . . ?
C16 C20 C21 C17 0.27(17) . . . . ?
C16 C20 C21 C22 -89.13(17) . . . . ?
C16 C20 C21 C23 136.4(2) . . . . ?
C17 C16 C20 C19 -89.88(17) . . . . ?
C17 C16 C20 C21 -0.27(17) . . . . ?
C17 C18 C22 C19 88.81(16) . . . . ?
C17 C18 C22 C21 -0.33(16) . . . . ?
C17 C21 C22 C18 0.32(16) . . . . ?
C17 C21 C22 C19 -90.45(16) . . . . ?
C17 C21 C23 O5 119.7(3) . . . . ?
C17 C21 C23 O6 -60.8(3) . . . . ?
C18 C15 C16 C17 0.10(16) . . . . ?
C18 C15 C16 C20 -89.94(17) . . . . ?
C18 C15 C19 C20 89.97(16) . . . . ?
C18 C15 C19 C22 -0.74(16) . . . . ?
C18 C17 C21 C20 -90.87(17) . . . . ?
C18 C17 C21 C22 -0.33(16) . . . . ?
C18 C17 C21 C23 130.0(2) . . . . ?
C19 C15 C16 C17 90.19(16) . . . . ?
C19 C15 C16 C20 0.15(16) . . . . ?
C19 C15 C18 C17 -89.43(16) . . . . ?
C19 C15 C18 C22 0.74(16) . . . . ?
C19 C20 C21 C17 89.87(17) . . . . ?
C19 C20 C21 C22 0.47(17) . . . . ?
C19 C20 C21 C23 -134.0(2) . . . . ?
C20 C16 C17 C18 90.54(17) . . . . ?
C20 C16 C17 C21 0.27(17) . . . . ?
C20 C19 C22 C18 -89.69(17) . . . . ?
C20 C19 C22 C21 0.47(17) . . . . ?
C20 C21 C22 C18 90.31(17) . . . . ?
C20 C21 C22 C19 -0.47(17) . . . . ?
C20 C21 C23 O5 -3.3(4) . . . . ?
C20 C21 C23 O6 176.1(2) . . . . ?
C21 C17 C18 C15 89.86(16) . . . . ?
C21 C17 C18 C22 0.33(16) . . . . ?
C22 C19 C20 C16 89.75(17) . . . . ?
C22 C19 C20 C21 -0.47(17) . . . . ?
C22 C21 C23 O5 -125.3(3) . . . . ?
C22 C21 C23 O6 54.1(3) . . . . ?
C23 C21 C22 C18 -131.1(2) . . . . ?
C23 C21 C22 C19 138.1(2) . . . . ?
C24 O6 C23 O5 1.4(4) . . . . ?
C24 O6 C23 C21 -178.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.685

####################################################################### 
# 
# 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_rh059
_database_code_depnum_ccdc_archive 'CCDC 1854642'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 Cl N O3'
_chemical_formula_sum            'C13 H14 Cl N O3'
_chemical_formula_weight         267.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H14 Cl N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1082(5)
_cell_length_b                   10.2539(6)
_cell_length_c                   25.5319(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2384.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.4850
_cell_measurement_theta_min      3.4240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.853
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4478
_exptl_crystal_size_mid          0.1536
_exptl_crystal_size_min          0.0469
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.247
_diffrn_reflns_theta_min         3.462
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -119.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298  -27.0000   77.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega   65.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9298  168.0000  103.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega   32.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -27.0000   77.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00  117.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -115.0000 -130.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  101.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  100.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -50.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298   38.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298   38.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  8 omega   33.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  9 omega   26.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 10 omega   33.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega   33.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -30.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega -116.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298  -38.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega -115.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9298  -57.0000  -60.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1593204000
_diffrn_orient_matrix_UB_12      0.0497269000
_diffrn_orient_matrix_UB_13      0.0043883000
_diffrn_orient_matrix_UB_21      0.0199330000
_diffrn_orient_matrix_UB_22      -0.0185264000
_diffrn_orient_matrix_UB_23      -0.0594215000
_diffrn_orient_matrix_UB_31      -0.0531171000
_diffrn_orient_matrix_UB_32      0.1406531000
_diffrn_orient_matrix_UB_33      -0.0093353000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1904
_reflns_number_total             2425
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.017
_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)+(0.1260P)²+1.1614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.2002
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.99461(8) 0.60432(7) 0.33549(3) 0.0279(3) Uani 1 1 d . . . . .
O1 O 0.7642(2) 0.9111(2) 0.42617(8) 0.0223(5) Uani 1 1 d . . . . .
O2 O 0.8612(2) 0.7336(2) 0.69080(8) 0.0265(5) Uani 1 1 d . . . . .
O3 O 0.6794(3) 0.5911(2) 0.67393(8) 0.0234(5) Uani 1 1 d . . . . .
N1 N 0.7400(3) 0.6949(2) 0.40999(9) 0.0189(5) Uani 1 1 d . . . . .
H1 H 0.739(4) 0.617(4) 0.4210(16) 0.023 Uiso 1 1 d R . . . .
C1 C 0.8672(3) 0.7367(3) 0.32608(11) 0.0241(6) Uani 1 1 d . . . . .
H1A H 0.9110 0.8185 0.3395 0.029 Uiso 1 1 calc R . . . .
H1B H 0.8482 0.7482 0.2882 0.029 Uiso 1 1 calc R . . . .
C2 C 0.7241(3) 0.7109(3) 0.35407(11) 0.0239(6) Uani 1 1 d . . . . .
H2A H 0.6561 0.7843 0.3472 0.029 Uiso 1 1 calc R . . . .
H2B H 0.6791 0.6310 0.3393 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7569(3) 0.7974(3) 0.44210(10) 0.0167(5) Uani 1 1 d . . . . .
C4 C 0.7620(3) 0.7659(3) 0.49954(10) 0.0167(5) Uani 1 1 d . . . . .
C5 C 0.7587(3) 0.6271(3) 0.52455(10) 0.0181(6) Uani 1 1 d . . . . .
H5 H 0.7537 0.5435 0.5044 0.022 Uiso 1 1 calc R . . . .
C6 C 0.6421(3) 0.6736(3) 0.56535(10) 0.0180(6) Uani 1 1 d . . . . .
H6 H 0.5512 0.6247 0.5752 0.022 Uiso 1 1 calc R . . . .
C7 C 0.6457(3) 0.8142(3) 0.54103(10) 0.0172(5) Uani 1 1 d . . . . .
H7 H 0.5576 0.8690 0.5331 0.021 Uiso 1 1 calc R . . . .
C8 C 0.8891(3) 0.8065(3) 0.53828(10) 0.0183(6) Uani 1 1 d . . . . .
H8 H 0.9798 0.8556 0.5283 0.022 Uiso 1 1 calc R . . . .
C9 C 0.8859(3) 0.6661(3) 0.56265(10) 0.0197(6) Uani 1 1 d . . . . .
H9 H 0.9740 0.6115 0.5707 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7681(3) 0.7130(3) 0.60385(11) 0.0187(6) Uani 1 1 d . . . . .
C11 C 0.7732(3) 0.8524(3) 0.57931(11) 0.0197(6) Uani 1 1 d . . . . .
H11 H 0.7785 0.9355 0.5997 0.024 Uiso 1 1 calc R . . . .
C12 C 0.7764(3) 0.6844(3) 0.66070(11) 0.0201(6) Uani 1 1 d . . . . .
C13 C 0.6755(4) 0.5531(3) 0.72825(11) 0.0306(7) Uani 1 1 d . . . . .
H13A H 0.6171 0.4734 0.7320 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.6311 0.6231 0.7490 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.7757 0.5370 0.7406 0.046 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 1.802(3) . ?
O1 C3 1.236(3) . ?
O2 C12 1.201(4) . ?
O3 C12 1.346(4) . ?
O3 C13 1.441(3) . ?
N1 H1 0.85(4) . ?
N1 C2 1.444(3) . ?
N1 C3 1.342(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(3) . ?
C4 C5 1.560(4) . ?
C4 C7 1.578(4) . ?
C4 C8 1.579(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.563(4) . ?
C5 C9 1.564(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.570(4) . ?
C6 C10 1.564(4) . ?
C7 H7 1.0000 . ?
C7 C11 1.568(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.569(4) . ?
C8 C11 1.560(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.578(4) . ?
C10 C11 1.561(4) . ?
C10 C12 1.483(4) . ?
C11 H11 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 O3 C13 116.7(2) . . ?
C2 N1 H1 116(3) . . ?
C3 N1 H1 123(3) . . ?
C3 N1 C2 121.7(2) . . ?
Cl1 C1 H1A 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 Cl1 111.1(2) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 113.7(2) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 H2B 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 N1 123.0(3) . . ?
O1 C3 C4 121.5(3) . . ?
N1 C3 C4 115.5(2) . . ?
C3 C4 C5 126.6(2) . . ?
C3 C4 C7 124.5(2) . . ?
C3 C4 C8 125.3(2) . . ?
C5 C4 C7 89.9(2) . . ?
C5 C4 C8 89.90(19) . . ?
C7 C4 C8 89.37(19) . . ?
C4 C5 H5 124.9 . . ?
C4 C5 C6 90.4(2) . . ?
C4 C5 C9 90.4(2) . . ?
C6 C5 H5 124.9 . . ?
C6 C5 C9 90.6(2) . . ?
C9 C5 H5 124.9 . . ?
C5 C6 H6 125.3 . . ?
C5 C6 C7 90.1(2) . . ?
C5 C6 C10 89.9(2) . . ?
C7 C6 H6 125.3 . . ?
C10 C6 H6 125.3 . . ?
C10 C6 C7 89.8(2) . . ?
C4 C7 H7 125.4 . . ?
C6 C7 C4 89.5(2) . . ?
C6 C7 H7 125.4 . . ?
C11 C7 C4 90.0(2) . . ?
C11 C7 C6 89.90(19) . . ?
C11 C7 H7 125.4 . . ?
C4 C8 H8 125.4 . . ?
C9 C8 C4 89.5(2) . . ?
C9 C8 H8 125.4 . . ?
C11 C8 C4 90.2(2) . . ?
C11 C8 H8 125.4 . . ?
C11 C8 C9 89.9(2) . . ?
C5 C9 C8 90.1(2) . . ?
C5 C9 H9 125.4 . . ?
C5 C9 C10 89.4(2) . . ?
C8 C9 H9 125.4 . . ?
C8 C9 C10 89.8(2) . . ?
C10 C9 H9 125.4 . . ?
C6 C10 C9 90.1(2) . . ?
C11 C10 C6 90.4(2) . . ?
C11 C10 C9 89.5(2) . . ?
C12 C10 C6 127.0(2) . . ?
C12 C10 C9 123.9(2) . . ?
C12 C10 C11 124.9(2) . . ?
C7 C11 H11 125.0 . . ?
C8 C11 C7 90.4(2) . . ?
C8 C11 C10 90.8(2) . . ?
C8 C11 H11 125.0 . . ?
C10 C11 C7 90.0(2) . . ?
C10 C11 H11 125.0 . . ?
O2 C12 O3 124.1(3) . . ?
O2 C12 C10 125.2(3) . . ?
O3 C12 C10 110.7(2) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 N1 60.1(3) . . . . ?
O1 C3 C4 C5 -178.0(3) . . . . ?
O1 C3 C4 C7 61.5(4) . . . . ?
O1 C3 C4 C8 -56.5(4) . . . . ?
N1 C3 C4 C5 3.8(4) . . . . ?
N1 C3 C4 C7 -116.7(3) . . . . ?
N1 C3 C4 C8 125.2(3) . . . . ?
C2 N1 C3 O1 -2.1(4) . . . . ?
C2 N1 C3 C4 176.1(2) . . . . ?
C3 N1 C2 C1 78.2(3) . . . . ?
C3 C4 C5 C6 -134.1(3) . . . . ?
C3 C4 C5 C9 135.2(3) . . . . ?
C3 C4 C7 C6 135.6(3) . . . . ?
C3 C4 C7 C11 -134.5(3) . . . . ?
C3 C4 C8 C9 -136.1(3) . . . . ?
C3 C4 C8 C11 134.0(3) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 C6 C10 -90.4(2) . . . . ?
C4 C5 C9 C8 0.6(2) . . . . ?
C4 C5 C9 C10 90.4(2) . . . . ?
C4 C7 C11 C8 0.7(2) . . . . ?
C4 C7 C11 C10 -90.1(2) . . . . ?
C4 C8 C9 C5 -0.6(2) . . . . ?
C4 C8 C9 C10 -90.0(2) . . . . ?
C4 C8 C11 C7 -0.7(2) . . . . ?
C4 C8 C11 C10 89.3(2) . . . . ?
C5 C4 C7 C6 -0.65(19) . . . . ?
C5 C4 C7 C11 89.2(2) . . . . ?
C5 C4 C8 C9 0.6(2) . . . . ?
C5 C4 C8 C11 -89.3(2) . . . . ?
C5 C6 C7 C4 0.65(19) . . . . ?
C5 C6 C7 C11 -89.3(2) . . . . ?
C5 C6 C10 C9 0.0(2) . . . . ?
C5 C6 C10 C11 89.5(2) . . . . ?
C5 C6 C10 C12 -134.3(3) . . . . ?
C5 C9 C10 C6 0.0(2) . . . . ?
C5 C9 C10 C11 -90.4(2) . . . . ?
C5 C9 C10 C12 136.5(3) . . . . ?
C6 C5 C9 C8 -89.8(2) . . . . ?
C6 C5 C9 C10 0.0(2) . . . . ?
C6 C7 C11 C8 90.2(2) . . . . ?
C6 C7 C11 C10 -0.6(2) . . . . ?
C6 C10 C11 C7 0.6(2) . . . . ?
C6 C10 C11 C8 -89.8(2) . . . . ?
C6 C10 C12 O2 -167.0(3) . . . . ?
C6 C10 C12 O3 15.5(4) . . . . ?
C7 C4 C5 C6 0.7(2) . . . . ?
C7 C4 C5 C9 -90.0(2) . . . . ?
C7 C4 C8 C9 90.5(2) . . . . ?
C7 C4 C8 C11 0.66(19) . . . . ?
C7 C6 C10 C9 -90.1(2) . . . . ?
C7 C6 C10 C11 -0.6(2) . . . . ?
C7 C6 C10 C12 135.6(3) . . . . ?
C8 C4 C5 C6 90.0(2) . . . . ?
C8 C4 C5 C9 -0.6(2) . . . . ?
C8 C4 C7 C6 -90.56(19) . . . . ?
C8 C4 C7 C11 -0.66(19) . . . . ?
C8 C9 C10 C6 90.1(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C8 C9 C10 C12 -133.4(3) . . . . ?
C9 C5 C6 C7 89.78(19) . . . . ?
C9 C5 C6 C10 0.0(2) . . . . ?
C9 C8 C11 C7 -90.2(2) . . . . ?
C9 C8 C11 C10 -0.3(2) . . . . ?
C9 C10 C11 C7 90.7(2) . . . . ?
C9 C10 C11 C8 0.3(2) . . . . ?
C9 C10 C12 O2 72.6(4) . . . . ?
C9 C10 C12 O3 -105.0(3) . . . . ?
C10 C6 C7 C4 90.6(2) . . . . ?
C10 C6 C7 C11 0.6(2) . . . . ?
C11 C8 C9 C5 89.6(2) . . . . ?
C11 C8 C9 C10 0.3(2) . . . . ?
C11 C10 C12 O2 -44.6(4) . . . . ?
C11 C10 C12 O3 137.9(3) . . . . ?
C12 C10 C11 C7 -137.0(3) . . . . ?
C12 C10 C11 C8 132.6(3) . . . . ?
C13 O3 C12 O2 2.4(4) . . . . ?
C13 O3 C12 C10 179.9(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 6 -4 0.1955 0.0045 6.0055 -3.9807 0.2819 0.1254 0.8816
0 -6 4 0.2177 -0.0045 -6.0055 3.9807 -0.2819 -0.1254 -0.8816
6 0 -1 0.0871 6.0004 -0.0019 -1.0211 0.9514 0.1803 -0.3095
-6 0 1 0.0601 -6.0004 0.0019 1.0211 -0.9514 -0.1803 0.3095
-1 0 -16 0.0235 -1.0004 0.0166 -15.9935 -0.2287 0.9301 0.2048
1 0 16 0.0235 1.0004 -0.0166 15.9935 0.2287 -0.9301 -0.2048

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'

