# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_g151224a
_database_code_depnum_ccdc_archive 'CCDC 1447840'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2015-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
"(1S,1R,6R)-tert-butyl 6'-chloro-2'-oxo-6,6a-dihydro-1H-spiro[cyclopropa[a]indene-1,3'-indoline]-1'-carboxylate"
_chemical_formula_moiety         'C22 H19 Cl N O3'
_chemical_formula_sum            'C22 H19 Cl N O3'
_chemical_formula_weight         380.83
_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 0.0181 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.3670(3)
_cell_length_b                   12.1881(3)
_cell_length_c                   21.7372(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1951.79(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5148
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7470
_cell_measurement_theta_min      3.6620
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42467
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.1500
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15887
_diffrn_reflns_theta_full        73.67
_diffrn_reflns_theta_max         73.67
_diffrn_reflns_theta_min         4.07
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093   37.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093   37.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00    5.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093   37.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1093  -99.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   25.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1093 -125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega  107.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  111.0000 -180.0000 68

#__ type_ start__ end____ width___ exp.time_
  8 omega   31.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 10 omega   33.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega  107.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  111.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   56.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 13 omega  105.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   61.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega -114.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093  -57.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 15 omega -114.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093  -60.0000   13.0000 104

#__ type_ start__ end____ width___ exp.time_
 16 omega -114.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093  -57.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 17 omega   75.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 18 omega   28.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522 -111.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   15.0000  150.0000 133
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0975918000
_diffrn_orient_matrix_UB_12      -0.0106885000
_diffrn_orient_matrix_UB_13      -0.0623841000
_diffrn_orient_matrix_UB_21      -0.1351217000
_diffrn_orient_matrix_UB_22      -0.0900210000
_diffrn_orient_matrix_UB_23      -0.0194979000
_diffrn_orient_matrix_UB_31      -0.1261330000
_diffrn_orient_matrix_UB_32      0.0880763000
_diffrn_orient_matrix_UB_33      -0.0274884000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3257
_reflns_number_total             3871
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3871
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1482
_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. Rigid bond restraints
 C20, C21, C22, C20A, C21A, C22A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C20A \\sim C21A \\sim C22A: within 1.7A with
sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Fixed Sof: C20(0.5) H20A(0.5) H20B(0.5) H20C(0.5) C20A(0.5) H20D(0.5)
 H20E(0.5) H20F(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) C21A(0.5) H21D(0.5)
 H21E(0.5) H21F(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C22A(0.5) H22D(0.5)
 H22E(0.5) H22F(0.5)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C12(H12), C13(H13), C15(H15)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C21(H21A,H21B,H21C), C21A(H21D,
 H21E,H21F), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2632(5) -0.3646(3) -0.03778(16) 0.0735(8) Uani 1 d . . . .
H1 H 0.3680 -0.3828 -0.0162 0.088 Uiso 1 calc . . R .
C2 C 0.2726(7) -0.3073(3) -0.0928(2) 0.0937(13) Uani 1 d . . . .
H2 H 0.3847 -0.2856 -0.1083 0.112 Uiso 1 calc . . R .
C3 C 0.1162(9) -0.2826(3) -0.12465(18) 0.1041(15) Uani 1 d . . . .
H3 H 0.1246 -0.2447 -0.1617 0.125 Uiso 1 calc . . R .
C4 C -0.0528(7) -0.3125(3) -0.10296(16) 0.0895(11) Uani 1 d . . . .
H4 H -0.1571 -0.2954 -0.1251 0.107 Uiso 1 calc . . R .
C5 C -0.0642(5) -0.3687(2) -0.04743(13) 0.0649(7) Uani 1 d . . . .
C6 C 0.0930(4) -0.3941(2) -0.01573(13) 0.0565(6) Uani 1 d . . . .
C7 C 0.0499(4) -0.4524(2) 0.04243(11) 0.0539(5) Uani 1 d . . . .
H7 H 0.1149 -0.4330 0.0802 0.065 Uiso 1 calc . . R .
C8 C -0.1538(4) -0.4618(2) 0.04336(13) 0.0584(6) Uani 1 d . . . .
H8 H -0.2170 -0.4494 0.0824 0.070 Uiso 1 calc . . R .
C9 C -0.2289(4) -0.4088(3) -0.01374(16) 0.0691(8) Uani 1 d . . . .
H9 H -0.3498 -0.4025 -0.0255 0.083 Uiso 1 calc . . R .
C10 C -0.0389(4) -0.56640(19) 0.03654(9) 0.0504(5) Uani 1 d . . . .
C11 C -0.0343(4) -0.64521(19) -0.01538(10) 0.0479(5) Uani 1 d . . . .
C12 C -0.0314(5) -0.6320(2) -0.07851(11) 0.0610(6) Uani 1 d . . . .
H12 H -0.0303 -0.5621 -0.0957 0.073 Uiso 1 calc . . R .
C13 C -0.0302(5) -0.7252(2) -0.11621(10) 0.0607(6) Uani 1 d . . . .
H13 H -0.0251 -0.7177 -0.1588 0.073 Uiso 1 calc . . R .
C14 C -0.0364(4) -0.82742(19) -0.09020(10) 0.0513(5) Uani 1 d . . . .
C15 C -0.0390(4) -0.84363(19) -0.02712(10) 0.0505(5) Uani 1 d . . . .
H15 H -0.0424 -0.9137 -0.0102 0.061 Uiso 1 calc . . R .
C16 C -0.0362(3) -0.75090(18) 0.00961(9) 0.0450(4) Uani 1 d . . . .
C17 C -0.0318(4) -0.6332(2) 0.09377(10) 0.0545(5) Uani 1 d . . . .
C18 C -0.0325(4) -0.8376(2) 0.11348(10) 0.0533(5) Uani 1 d . . . .
C19 C -0.0368(6) -0.8926(3) 0.22112(12) 0.0783(9) Uani 1 d . . . .
C20 C -0.109(3) -0.817(3) 0.2785(11) 0.124(7) Uani 0.50 d A 1 . U
H20A H -0.1005 -0.8581 0.3161 0.186 Uiso 0.50 calc A 1 GR .
H20B H -0.2334 -0.7968 0.2715 0.186 Uiso 0.50 calc A 1 GR .
H20C H -0.0360 -0.7521 0.2816 0.186 Uiso 0.50 calc A 1 GR .
C20A C -0.006(3) -0.827(3) 0.2763(11) 0.125(7) Uani 0.50 d A 2 . U
H20D H -0.0689 -0.7583 0.2725 0.188 Uiso 0.50 calc A 2 GR .
H20E H 0.1215 -0.8137 0.2811 0.188 Uiso 0.50 calc A 2 GR .
H20F H -0.0510 -0.8659 0.3116 0.188 Uiso 0.50 calc A 2 GR .
C21 C -0.181(6) -0.987(2) 0.2142(17) 0.086(4) Uani 0.50 d A 1 . U
H21A H -0.1923 -1.0252 0.2525 0.129 Uiso 0.50 calc A 1 GR .
H21B H -0.1420 -1.0369 0.1827 0.129 Uiso 0.50 calc A 1 GR .
H21C H -0.2959 -0.9557 0.2030 0.129 Uiso 0.50 calc A 1 GR .
C21A C -0.202(6) -0.954(2) 0.2185(17) 0.087(4) Uani 0.50 d A 2 . U
H21D H -0.1984 -1.0111 0.2487 0.130 Uiso 0.50 calc A 2 GR .
H21E H -0.2151 -0.9851 0.1783 0.130 Uiso 0.50 calc A 2 GR .
H21F H -0.3021 -0.9058 0.2268 0.130 Uiso 0.50 calc A 2 GR .
C22 C 0.149(3) -0.9235(16) 0.2285(9) 0.114(5) Uani 0.50 d A 1 . U
H22A H 0.2218 -0.8590 0.2350 0.170 Uiso 0.50 calc A 1 GR .
H22B H 0.1905 -0.9606 0.1921 0.170 Uiso 0.50 calc A 1 GR .
H22C H 0.1611 -0.9715 0.2633 0.170 Uiso 0.50 calc A 1 GR .
C22A C 0.131(3) -0.9744(14) 0.2127(9) 0.113(5) Uani 0.50 d A 2 . U
H22D H 0.1114 -1.0194 0.1771 0.170 Uiso 0.50 calc A 2 GR .
H22E H 0.1414 -1.0203 0.2485 0.170 Uiso 0.50 calc A 2 GR .
H22F H 0.2404 -0.9328 0.2076 0.170 Uiso 0.50 calc A 2 GR .
Cl1 Cl -0.03981(13) -0.94194(6) -0.13809(3) 0.0742(2) Uani 1 d . . . .
N1 N -0.0360(3) -0.74471(16) 0.07530(8) 0.0505(4) Uani 1 d . . . .
O1 O -0.0282(4) -0.59948(16) 0.14569(8) 0.0769(6) Uani 1 d . . . .
O2 O -0.0196(4) -0.92827(16) 0.09384(8) 0.0825(8) Uani 1 d . . . .
O3 O -0.0447(4) -0.80938(16) 0.17107(8) 0.0839(7) Uani 1 d A . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C1 C6 1.390(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(4) . ?
C5 C6 1.383(4) . ?
C5 C9 1.499(5) . ?
C6 C7 1.484(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.505(4) . ?
C7 C10 1.541(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.505(4) . ?
C8 C10 1.537(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.482(3) . ?
C10 C17 1.488(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.398(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(4) . ?
C14 C15 1.385(3) . ?
C14 Cl1 1.741(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 N1 1.430(2) . ?
C17 N1 1.417(3) . ?
C17 O1 1.202(3) . ?
C18 N1 1.404(3) . ?
C18 O2 1.188(3) . ?
C18 O3 1.301(3) . ?
C19 C20 1.64(2) . ?
C19 C20A 1.46(3) . ?
C19 C21 1.57(4) . ?
C19 C21A 1.42(4) . ?
C19 C22 1.43(3) . ?
C19 C22A 1.60(3) . ?
C19 O3 1.489(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.9 . . ?
C2 C1 C6 118.2(4) . . ?
C6 C1 H1 120.9 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C9 129.3(4) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 C9 111.2(2) . . ?
C1 C6 C7 127.6(3) . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 C7 110.6(2) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 105.1(2) . . ?
C6 C7 C10 116.85(19) . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C10 60.57(19) . . ?
C10 C7 H7 119.6 . . ?
C7 C8 H8 118.3 . . ?
C7 C8 C10 60.87(18) . . ?
C9 C8 C7 108.8(2) . . ?
C9 C8 H8 118.3 . . ?
C9 C8 C10 118.6(2) . . ?
C10 C8 H8 118.3 . . ?
C5 C9 C8 104.2(2) . . ?
C5 C9 H9 127.9 . . ?
C8 C9 H9 127.9 . . ?
C8 C10 C7 58.56(17) . . ?
C11 C10 C7 129.6(2) . . ?
C11 C10 C8 128.6(2) . . ?
C11 C10 C17 106.32(19) . . ?
C17 C10 C7 114.15(19) . . ?
C17 C10 C8 113.1(2) . . ?
C12 C11 C10 132.9(2) . . ?
C12 C11 C16 119.6(2) . . ?
C16 C11 C10 107.52(18) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 122.6(2) . . ?
C13 C14 Cl1 118.87(17) . . ?
C15 C14 Cl1 118.50(18) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.0(2) . . ?
C16 C15 H15 121.5 . . ?
C11 C16 N1 109.83(18) . . ?
C15 C16 C11 121.91(19) . . ?
C15 C16 N1 128.3(2) . . ?
N1 C17 C10 106.70(18) . . ?
O1 C17 C10 126.8(2) . . ?
O1 C17 N1 126.5(2) . . ?
O2 C18 N1 122.6(2) . . ?
O2 C18 O3 126.7(2) . . ?
O3 C18 N1 110.7(2) . . ?
C20A C19 C20 28.0(14) . . ?
C20A C19 C21 125.8(17) . . ?
C20A C19 C22A 108.4(11) . . ?
C20A C19 O3 103.5(13) . . ?
C21 C19 C20 105.3(15) . . ?
C21 C19 C22A 93.2(13) . . ?
C21A C19 C20 92.6(15) . . ?
C21A C19 C20A 116.8(16) . . ?
C21A C19 C21 16(2) . . ?
C21A C19 C22 133.2(13) . . ?
C21A C19 C22A 109.2(11) . . ?
C21A C19 O3 107.1(15) . . ?
C22 C19 C20 112.0(12) . . ?
C22 C19 C20A 84.5(12) . . ?
C22 C19 C21 117.8(14) . . ?
C22 C19 C22A 26.9(9) . . ?
C22 C19 O3 107.3(8) . . ?
C22A C19 C20 133.5(12) . . ?
O3 C19 C20 99.3(11) . . ?
O3 C19 C21 113.7(15) . . ?
O3 C19 C22A 111.8(7) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C19 C20A H20D 109.5 . . ?
C19 C20A H20E 109.5 . . ?
C19 C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
C19 C21A H21D 109.5 . . ?
C19 C21A H21E 109.5 . . ?
C19 C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
C19 C22A H22D 109.5 . . ?
C19 C22A H22E 109.5 . . ?
C19 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C17 N1 C16 109.48(17) . . ?
C18 N1 C16 123.20(18) . . ?
C18 N1 C17 127.26(18) . . ?
C18 O3 C19 121.3(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
C1 C2 C3 C4 0.6(6) . . . . ?
C1 C6 C7 C8 179.5(3) . . . . ?
C1 C6 C7 C10 -116.2(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C3 C4 C5 C9 179.2(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C4 C5 C9 C8 -179.4(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C10 64.9(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
C6 C5 C9 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C6 C7 C8 C10 112.6(2) . . . . ?
C6 C7 C10 C8 -92.9(3) . . . . ?
C6 C7 C10 C11 23.3(4) . . . . ?
C6 C7 C10 C17 163.8(2) . . . . ?
C7 C8 C9 C5 -0.1(3) . . . . ?
C7 C8 C10 C11 -117.9(3) . . . . ?
C7 C8 C10 C17 105.1(2) . . . . ?
C7 C10 C11 C12 -34.8(5) . . . . ?
C7 C10 C11 C16 146.2(3) . . . . ?
C7 C10 C17 N1 -153.1(2) . . . . ?
C7 C10 C17 O1 28.7(4) . . . . ?
C8 C7 C10 C11 116.2(3) . . . . ?
C8 C7 C10 C17 -103.3(3) . . . . ?
C8 C10 C11 C12 43.3(5) . . . . ?
C8 C10 C11 C16 -135.7(3) . . . . ?
C8 C10 C17 N1 142.3(2) . . . . ?
C8 C10 C17 O1 -35.8(4) . . . . ?
C9 C5 C6 C1 -179.6(3) . . . . ?
C9 C5 C6 C7 -0.7(3) . . . . ?
C9 C8 C10 C7 96.7(3) . . . . ?
C9 C8 C10 C11 -21.2(4) . . . . ?
C9 C8 C10 C17 -158.2(2) . . . . ?
C10 C7 C8 C9 -112.9(2) . . . . ?
C10 C8 C9 C5 -66.5(3) . . . . ?
C10 C11 C12 C13 -179.0(3) . . . . ?
C10 C11 C16 C15 177.8(2) . . . . ?
C10 C11 C16 N1 -1.8(3) . . . . ?
C10 C17 N1 C16 2.9(3) . . . . ?
C10 C17 N1 C18 -179.8(3) . . . . ?
C11 C10 C17 N1 -3.9(3) . . . . ?
C11 C10 C17 O1 178.0(3) . . . . ?
C11 C12 C13 C14 1.6(5) . . . . ?
C11 C16 N1 C17 -0.7(3) . . . . ?
C11 C16 N1 C18 -178.1(3) . . . . ?
C12 C11 C16 C15 -1.3(4) . . . . ?
C12 C11 C16 N1 179.0(3) . . . . ?
C12 C13 C14 C15 -1.8(5) . . . . ?
C12 C13 C14 Cl1 178.6(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 1.2(4) . . . . ?
C14 C15 C16 N1 -179.3(3) . . . . ?
C15 C16 N1 C17 179.7(3) . . . . ?
C15 C16 N1 C18 2.3(4) . . . . ?
C16 C11 C12 C13 -0.1(5) . . . . ?
C17 C10 C11 C12 -177.5(3) . . . . ?
C17 C10 C11 C16 3.5(3) . . . . ?
C20 C19 O3 C18 -166.4(10) . . . . ?
C20A C19 O3 C18 165.4(9) . . . . ?
C21 C19 O3 C18 -55.1(13) . . . . ?
C21A C19 O3 C18 -70.7(12) . . . . ?
C22 C19 O3 C18 77.0(9) . . . . ?
C22A C19 O3 C18 48.8(8) . . . . ?
Cl1 C14 C15 C16 -180.0(2) . . . . ?
N1 C18 O3 C19 -177.6(3) . . . . ?
O1 C17 N1 C16 -179.0(3) . . . . ?
O1 C17 N1 C18 -1.7(5) . . . . ?
O2 C18 N1 C16 4.1(5) . . . . ?
O2 C18 N1 C17 -172.8(3) . . . . ?
O2 C18 O3 C19 2.3(6) . . . . ?
O3 C18 N1 C16 -176.0(3) . . . . ?
O3 C18 N1 C17 7.1(5) . . . . ?

_olex2_date_sample_data_collection 2015-12-24
_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_g151231a
_database_code_depnum_ccdc_archive 'CCDC 1447842'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2016-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H20 Cl N O3'
_chemical_formula_sum            'C21 H20 Cl N O3'
_chemical_formula_weight         369.83
_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 0.0181 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   11.3609(3)
_cell_length_b                   11.3606(3)
_cell_length_c                   14.5605(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1879.28(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.3840
_cell_measurement_theta_min      3.0210
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15591
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20872
_diffrn_reflns_theta_full        73.61
_diffrn_reflns_theta_max         73.61
_diffrn_reflns_theta_min         4.94
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000 -150.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   77.0000   30.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843   37.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843 -125.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega   59.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   51.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   25.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   47.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522 -111.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 12 omega   75.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 14 omega   77.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 15 omega   22.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega  121.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   61.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   76.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   61.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 19 omega -114.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 20 omega -119.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -77.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
 21 omega -116.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -37.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
 22 omega   -4.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843  -99.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
 23 omega    6.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843   77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
 24 omega   72.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   77.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
 25 omega   75.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   30.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
 26 omega   78.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   45.0000 -150.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1030229000
_diffrn_orient_matrix_UB_12      -0.0397462000
_diffrn_orient_matrix_UB_13      -0.0614895000
_diffrn_orient_matrix_UB_21      -0.0881978000
_diffrn_orient_matrix_UB_22      0.0446428000
_diffrn_orient_matrix_UB_23      0.0724266000
_diffrn_orient_matrix_UB_31      -0.0013264000
_diffrn_orient_matrix_UB_32      0.1217070000
_diffrn_orient_matrix_UB_33      -0.0465422000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3458
_reflns_number_total             3725
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.0045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.4163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1361
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 1.7A with sigma of
0.003 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
4.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.9661(3) 0.4157(3) 0.0782(2) 0.0679(7) Uani 1 d . . . U
C2 C 1.0318(4) 0.3616(3) 0.0107(3) 0.0848(8) Uani 1 d . . . U
H2 H 0.9963 0.3338 -0.0426 0.102 Uiso 1 calc . . R .
C3 C 1.1520(4) 0.3496(3) 0.0243(3) 0.0924(9) Uani 1 d . . . U
H3 H 1.1975 0.3123 -0.0201 0.111 Uiso 1 calc . . R .
C4 C 1.2049(4) 0.3920(4) 0.1022(3) 0.0887(9) Uani 1 d . . . U
H4 H 1.2857 0.3839 0.1101 0.106 Uiso 1 calc . . R .
C5 C 1.1378(3) 0.4472(3) 0.1696(3) 0.0749(7) Uani 1 d . . . U
H5 H 1.1741 0.4759 0.2222 0.090 Uiso 1 calc . . R .
C6 C 1.0164(3) 0.4599(2) 0.1587(2) 0.0598(6) Uani 1 d . . . U
C7 C 0.9410(2) 0.5163(2) 0.22909(19) 0.0517(6) Uani 1 d . . . .
H7 H 0.8768 0.4664 0.2514 0.062 Uiso 1 calc . . R .
C8 C 0.9832(3) 0.6037(3) 0.2968(2) 0.0603(7) Uani 1 d . . . .
H8A H 1.0662 0.6237 0.2958 0.072 Uiso 1 calc . . R .
H8B H 0.9481 0.6022 0.3575 0.072 Uiso 1 calc . . R .
C9 C 0.9076(2) 0.6473(2) 0.21800(17) 0.0433(5) Uani 1 d . . . .
C10 C 0.9484(2) 0.7264(2) 0.14467(16) 0.0407(5) Uani 1 d . . . .
C11 C 0.8536(2) 0.7980(2) 0.12005(16) 0.0396(5) Uani 1 d . . . .
C12 C 0.8643(2) 0.8845(2) 0.05341(18) 0.0505(6) Uani 1 d . . . .
H12 H 0.8008 0.9317 0.0369 0.061 Uiso 1 calc . . R .
C13 C 0.9738(3) 0.8976(3) 0.0123(2) 0.0579(7) Uani 1 d . . . .
H13 H 0.9833 0.9549 -0.0327 0.069 Uiso 1 calc . . R .
C14 C 1.0687(3) 0.8286(3) 0.0358(2) 0.0573(7) Uani 1 d . . . .
H14 H 1.1410 0.8396 0.0070 0.069 Uiso 1 calc . . R .
C15 C 1.0561(2) 0.7425(2) 0.1031(2) 0.0514(6) Uani 1 d . . . .
H15 H 1.1200 0.6960 0.1198 0.062 Uiso 1 calc . . R .
C16 C 0.7821(2) 0.6768(2) 0.23591(16) 0.0423(5) Uani 1 d . . . .
C17 C 0.6471(2) 0.8317(2) 0.17208(18) 0.0441(5) Uani 1 d . . . .
C18 C 0.4407(2) 0.8200(2) 0.21522(19) 0.0485(6) Uani 1 d . . . .
C19 C 0.4525(3) 0.9059(3) 0.2943(2) 0.0631(7) Uani 1 d . . . .
H19A H 0.5024 0.9701 0.2762 0.095 Uiso 1 calc . . GR .
H19B H 0.4865 0.8664 0.3462 0.095 Uiso 1 calc . . GR .
H19C H 0.3762 0.9356 0.3105 0.095 Uiso 1 calc . . GR .
C20 C 0.3937(3) 0.8777(3) 0.1289(2) 0.0627(7) Uani 1 d . . . .
H20A H 0.3123 0.8976 0.1375 0.094 Uiso 1 calc . . GR .
H20B H 0.4010 0.8241 0.0782 0.094 Uiso 1 calc . . GR .
H20C H 0.4379 0.9478 0.1163 0.094 Uiso 1 calc . . GR .
C21 C 0.3678(3) 0.7139(3) 0.2421(3) 0.0659(8) Uani 1 d . . . .
H21A H 0.4026 0.6764 0.2945 0.099 Uiso 1 calc . . GR .
H21B H 0.3652 0.6594 0.1917 0.099 Uiso 1 calc . . GR .
H21C H 0.2893 0.7387 0.2569 0.099 Uiso 1 calc . . GR .
Cl1 Cl 0.81477(8) 0.43179(10) 0.06028(7) 0.0879(3) Uani 1 d . . . .
N1 N 0.75220(17) 0.76521(17) 0.17174(14) 0.0414(4) Uani 1 d . . . .
O1 O 0.71857(17) 0.63579(17) 0.29395(14) 0.0564(5) Uani 1 d . . . .
O2 O 0.64648(18) 0.93399(17) 0.15051(16) 0.0646(6) Uani 1 d . . . .
O3 O 0.55820(14) 0.76604(15) 0.19736(13) 0.0477(4) Uani 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
C1 C2 1.379(5) . ?
C1 C6 1.397(5) . ?
C1 Cl1 1.748(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(5) . ?
C6 C7 1.481(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.479(4) . ?
C7 C9 1.544(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.516(3) . ?
C9 C10 1.471(3) . ?
C9 C16 1.487(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.377(3) . ?
C11 C12 1.386(3) . ?
C11 N1 1.426(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9300 . ?
C16 N1 1.413(3) . ?
C16 O1 1.206(3) . ?
C17 N1 1.412(3) . ?
C17 O2 1.204(3) . ?
C17 O3 1.308(3) . ?
C18 C19 1.515(4) . ?
C18 C20 1.514(4) . ?
C18 C21 1.514(4) . ?
C18 O3 1.492(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.4(4) . . ?
C2 C1 Cl1 118.2(3) . . ?
C6 C1 Cl1 119.4(2) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 119.9(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 122.5(3) . . ?
C6 C7 H7 114.1 . . ?
C6 C7 C9 119.1(2) . . ?
C8 C7 C6 124.4(3) . . ?
C8 C7 H7 114.1 . . ?
C8 C7 C9 60.18(17) . . ?
C9 C7 H7 114.1 . . ?
C7 C8 H8A 117.6 . . ?
C7 C8 H8B 117.6 . . ?
C7 C8 C9 62.03(17) . . ?
H8A C8 H8B 114.7 . . ?
C9 C8 H8A 117.6 . . ?
C9 C8 H8B 117.6 . . ?
C8 C9 C7 57.78(18) . . ?
C10 C9 C7 126.0(2) . . ?
C10 C9 C8 124.8(2) . . ?
C10 C9 C16 106.94(19) . . ?
C16 C9 C7 115.8(2) . . ?
C16 C9 C8 118.9(2) . . ?
C11 C10 C9 107.44(19) . . ?
C15 C10 C9 132.9(2) . . ?
C15 C10 C11 119.6(2) . . ?
C10 C11 N1 109.58(19) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 N1 128.7(2) . . ?
C11 C12 H12 121.4 . . ?
C11 C12 C13 117.1(2) . . ?
C13 C12 H12 121.4 . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.2(2) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 119.6(3) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N1 C16 C9 105.97(19) . . ?
O1 C16 C9 127.6(2) . . ?
O1 C16 N1 126.4(2) . . ?
O2 C17 N1 121.3(2) . . ?
O2 C17 O3 128.2(2) . . ?
O3 C17 N1 110.4(2) . . ?
C20 C18 C19 112.5(2) . . ?
C21 C18 C19 111.4(3) . . ?
C21 C18 C20 111.4(3) . . ?
O3 C18 C19 108.5(2) . . ?
O3 C18 C20 110.4(2) . . ?
O3 C18 C21 102.0(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 N1 C11 109.89(18) . . ?
C17 N1 C11 123.03(19) . . ?
C17 N1 C16 125.5(2) . . ?
C17 O3 C18 120.38(19) . . ?

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
C1 C2 C3 C4 -1.0(6) . . . . ?
C1 C6 C7 C8 -155.6(3) . . . . ?
C1 C6 C7 C9 -83.5(3) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C7 -179.5(3) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C5 C6 C7 C8 25.2(4) . . . . ?
C5 C6 C7 C9 97.2(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C6 C7 C8 C9 106.7(3) . . . . ?
C6 C7 C9 C8 -115.2(3) . . . . ?
C6 C7 C9 C10 -3.1(4) . . . . ?
C6 C7 C9 C16 135.5(3) . . . . ?
C7 C8 C9 C10 -114.1(3) . . . . ?
C7 C8 C9 C16 103.8(3) . . . . ?
C7 C9 C10 C11 141.3(2) . . . . ?
C7 C9 C10 C15 -41.5(4) . . . . ?
C7 C9 C16 N1 -143.2(2) . . . . ?
C7 C9 C16 O1 37.8(4) . . . . ?
C8 C7 C9 C10 112.1(3) . . . . ?
C8 C7 C9 C16 -109.3(3) . . . . ?
C8 C9 C10 C11 -146.1(3) . . . . ?
C8 C9 C10 C15 31.2(4) . . . . ?
C8 C9 C16 N1 150.9(2) . . . . ?
C8 C9 C16 O1 -28.0(4) . . . . ?
C9 C10 C11 C12 178.7(2) . . . . ?
C9 C10 C11 N1 -2.4(3) . . . . ?
C9 C10 C15 C14 -178.1(3) . . . . ?
C9 C16 N1 C11 -4.3(2) . . . . ?
C9 C16 N1 C17 -170.3(2) . . . . ?
C10 C9 C16 N1 2.8(2) . . . . ?
C10 C9 C16 O1 -176.2(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 N1 C16 4.3(3) . . . . ?
C10 C11 N1 C17 170.7(2) . . . . ?
C11 C10 C15 C14 -1.1(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C11 N1 C16 -176.9(2) . . . . ?
C12 C11 N1 C17 -10.4(4) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C15 C10 C11 C12 1.0(4) . . . . ?
C15 C10 C11 N1 179.9(2) . . . . ?
C16 C9 C10 C11 -0.3(3) . . . . ?
C16 C9 C10 C15 177.0(3) . . . . ?
C19 C18 O3 C17 -62.1(3) . . . . ?
C20 C18 O3 C17 61.7(3) . . . . ?
C21 C18 O3 C17 -179.8(2) . . . . ?
Cl1 C1 C2 C3 179.4(3) . . . . ?
Cl1 C1 C6 C5 -178.8(2) . . . . ?
Cl1 C1 C6 C7 1.9(4) . . . . ?
N1 C11 C12 C13 -179.1(2) . . . . ?
N1 C17 O3 C18 171.7(2) . . . . ?
O1 C16 N1 C11 174.7(2) . . . . ?
O1 C16 N1 C17 8.7(4) . . . . ?
O2 C17 N1 C11 -20.9(4) . . . . ?
O2 C17 N1 C16 143.3(3) . . . . ?
O2 C17 O3 C18 -8.8(4) . . . . ?
O3 C17 N1 C11 158.5(2) . . . . ?
O3 C17 N1 C16 -37.2(3) . . . . ?

_olex2_date_sample_data_collection 2015-12-31
_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_g160416c
_database_code_depnum_ccdc_archive 'CCDC 1474970'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;
_audit_creation_date             2016-04-16
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 Cl N O4'
_chemical_formula_sum            'C23 H24 Cl N O4'
_chemical_formula_weight         413.88
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0330(5)
_cell_length_b                   9.8048(7)
_cell_length_c                   12.0153(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.156(5)
_cell_angle_gamma                90
_cell_volume                     1064.15(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      26.0920
_cell_measurement_theta_min      3.4870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78568
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5344
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.817
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   60.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -19.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00    8.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   62.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   77.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   14.00   1.0000    2.5900
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000   90.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0409883000
_diffrn_orient_matrix_UB_12      0.0135299000
_diffrn_orient_matrix_UB_13      0.0490333000
_diffrn_orient_matrix_UB_21      0.0210311000
_diffrn_orient_matrix_UB_22      -0.0644173000
_diffrn_orient_matrix_UB_23      0.0217211000
_diffrn_orient_matrix_UB_31      0.0636113000
_diffrn_orient_matrix_UB_32      0.0300422000
_diffrn_orient_matrix_UB_33      0.0246197000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.504
_reflns_Friedel_fraction_full    0.572
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                2690
_reflns_number_total             3006
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_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     267
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0362
_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)+(0.0436P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0857
_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:
 C2(H2), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;
_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 0.04593(11) 0.02664(11) 0.96698(9) 0.0651(3) Uani 1 1 d . . . . .
O1 O -0.3291(2) 0.4472(2) 1.39951(16) 0.0361(5) Uani 1 1 d . . . . .
O2 O -0.4423(2) 1.0628(2) 1.30579(17) 0.0402(6) Uani 1 1 d . . . . .
O6 O -0.0737(2) 0.3359(3) 1.47308(16) 0.0414(6) Uani 1 1 d . . . . .
O23 O 0.0828(2) 0.2708(3) 1.3377(2) 0.0635(9) Uani 1 1 d . . . . .
N3 N -0.1600(2) 0.3147(3) 1.29837(18) 0.0288(6) Uani 1 1 d . . . . .
C1 C -0.3760(3) 0.3851(3) 1.2074(2) 0.0274(7) Uani 1 1 d . . . . .
C2 C -0.5443(3) 0.3959(3) 1.2143(2) 0.0331(8) Uani 1 1 d . . . . .
H2 H -0.5810 0.4140 1.2895 0.040 Uiso 1 1 calc R . . . .
C3 C -0.4628(3) 0.5129(4) 1.1642(2) 0.0313(7) Uani 1 1 d . . . . .
H3 H -0.4709 0.5140 1.0829 0.038 Uiso 1 1 calc R . . . .
C4 C -0.4536(3) 0.6531(3) 1.2116(2) 0.0294(7) Uani 1 1 d . . . . .
C5 C -0.3608(3) 0.7485(4) 1.1610(2) 0.0344(8) Uani 1 1 d . . . . .
H5 H -0.2978 0.7202 1.1045 0.041 Uiso 1 1 calc R . . . .
C6 C -0.3604(3) 0.8847(4) 1.1932(2) 0.0350(7) Uani 1 1 d . . . . .
H6 H -0.2992 0.9468 1.1572 0.042 Uiso 1 1 calc R . . . .
C7 C -0.4514(3) 0.9276(4) 1.2791(2) 0.0317(7) Uani 1 1 d . . . . .
C8 C -0.5410(3) 0.8334(4) 1.3328(2) 0.0359(8) Uani 1 1 d . . . . .
H8 H -0.5998 0.8606 1.3921 0.043 Uiso 1 1 calc R . . . .
C9 C -0.5424(3) 0.6983(4) 1.2975(3) 0.0367(8) Uani 1 1 d . . . . .
H9 H -0.6049 0.6367 1.3327 0.044 Uiso 1 1 calc R . . . .
C10 C -0.5296(4) 1.1102(4) 1.3970(3) 0.0538(10) Uani 1 1 d . . . . .
H10A H -0.6327 1.1031 1.3783 0.081 Uiso 1 1 calc GR . . . .
H10B H -0.5055 1.2037 1.4124 0.081 Uiso 1 1 calc GR . . . .
H10C H -0.5092 1.0556 1.4616 0.081 Uiso 1 1 calc GR . . . .
C11 C -0.6441(3) 0.3040(4) 1.1466(3) 0.0454(9) Uani 1 1 d . . . . .
H11A H -0.7439 0.3374 1.1500 0.068 Uiso 1 1 calc GR . . . .
H11B H -0.6402 0.2132 1.1762 0.068 Uiso 1 1 calc GR . . . .
H11C H -0.6115 0.3031 1.0706 0.068 Uiso 1 1 calc GR . . . .
C12 C -0.2884(3) 0.2983(3) 1.1324(2) 0.0293(7) Uani 1 1 d . . . . .
C13 C -0.3102(3) 0.2572(4) 1.0234(2) 0.0377(8) Uani 1 1 d . . . . .
H13 H -0.3942 0.2849 0.9846 0.045 Uiso 1 1 calc R . . . .
C14 C -0.2062(3) 0.1743(4) 0.9724(3) 0.0412(8) Uani 1 1 d . . . . .
H14 H -0.2200 0.1465 0.8991 0.049 Uiso 1 1 calc R . . . .
C15 C -0.0830(4) 0.1336(4) 1.0304(3) 0.0397(8) Uani 1 1 d . . . . .
C16 C -0.0543(3) 0.1757(4) 1.1386(3) 0.0349(7) Uani 1 1 d . . . . .
H16 H 0.0312 0.1492 1.1762 0.042 Uiso 1 1 calc R . . . .
C17 C -0.1590(3) 0.2588(3) 1.1880(2) 0.0289(7) Uani 1 1 d . . . . .
C18 C -0.2921(3) 0.3917(3) 1.3143(2) 0.0279(7) Uani 1 1 d . . . . .
C19 C -0.0366(3) 0.3057(4) 1.3708(3) 0.0371(8) Uani 1 1 d . . . . .
C20 C 0.0451(4) 0.3482(4) 1.5613(3) 0.0501(10) Uani 1 1 d . . . . .
C21 C -0.0435(5) 0.3958(7) 1.6599(3) 0.096(2) Uani 1 1 d . . . . .
H21A H -0.0912 0.4806 1.6422 0.144 Uiso 1 1 calc GR . . . .
H21B H 0.0212 0.4084 1.7226 0.144 Uiso 1 1 calc GR . . . .
H21C H -0.1171 0.3287 1.6778 0.144 Uiso 1 1 calc GR . . . .
C22 C 0.1553(5) 0.4549(5) 1.5249(4) 0.0920(18) Uani 1 1 d . . . . .
H22A H 0.2137 0.4197 1.4648 0.138 Uiso 1 1 calc GR . . . .
H22B H 0.2188 0.4779 1.5863 0.138 Uiso 1 1 calc GR . . . .
H22C H 0.1033 0.5350 1.5005 0.138 Uiso 1 1 calc GR . . . .
C23 C 0.1180(5) 0.2136(4) 1.5825(3) 0.0628(12) Uani 1 1 d . . . . .
H23A H 0.0450 0.1487 1.6062 0.094 Uiso 1 1 calc GR . . . .
H23B H 0.1917 0.2239 1.6396 0.094 Uiso 1 1 calc GR . . . .
H23C H 0.1639 0.1819 1.5154 0.094 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 C15 1.744(3) . ?
O1 C18 1.207(3) . ?
O2 C7 1.366(4) . ?
O2 C10 1.429(4) . ?
O6 C19 1.309(4) . ?
O6 C20 1.511(3) . ?
O23 C19 1.201(4) . ?
N3 C17 1.435(4) . ?
N3 C18 1.426(4) . ?
N3 C19 1.415(4) . ?
C1 C2 1.527(4) . ?
C1 C3 1.566(4) . ?
C1 C12 1.472(4) . ?
C1 C18 1.491(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.490(5) . ?
C2 C11 1.510(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.490(5) . ?
C4 C5 1.396(4) . ?
C4 C9 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(4) . ?
C7 C8 1.388(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.383(4) . ?
C12 C17 1.400(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(5) . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C20 C21 1.506(6) . ?
C20 C22 1.509(6) . ?
C20 C23 1.496(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C10 117.6(3) . . ?
C19 O6 C20 119.6(2) . . ?
C18 N3 C17 109.5(2) . . ?
C19 N3 C17 122.5(2) . . ?
C19 N3 C18 127.5(2) . . ?
C2 C1 C3 57.60(19) . . ?
C12 C1 C2 127.6(2) . . ?
C12 C1 C3 121.9(2) . . ?
C12 C1 C18 106.3(2) . . ?
C18 C1 C2 117.0(2) . . ?
C18 C1 C3 120.3(2) . . ?
C1 C2 H2 113.7 . . ?
C3 C2 C1 62.51(19) . . ?
C3 C2 H2 113.7 . . ?
C3 C2 C11 122.5(3) . . ?
C11 C2 C1 121.5(3) . . ?
C11 C2 H2 113.7 . . ?
C1 C3 H3 112.0 . . ?
C2 C3 C1 59.9(2) . . ?
C2 C3 H3 112.0 . . ?
C4 C3 C1 125.7(2) . . ?
C4 C3 C2 125.7(2) . . ?
C4 C3 H3 112.0 . . ?
C5 C4 C3 119.0(3) . . ?
C9 C4 C3 123.3(3) . . ?
C9 C4 C5 117.4(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
O2 C7 C6 115.7(3) . . ?
O2 C7 C8 124.8(3) . . ?
C6 C7 C8 119.5(3) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 121.9(3) . . ?
C4 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 132.3(3) . . ?
C13 C12 C17 119.2(3) . . ?
C17 C12 C1 108.5(2) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Cl1 119.6(2) . . ?
C14 C15 C16 122.6(3) . . ?
C16 C15 Cl1 117.7(3) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.8(3) . . ?
C17 C16 H16 121.6 . . ?
C12 C17 N3 109.1(2) . . ?
C16 C17 N3 128.9(2) . . ?
C16 C17 C12 122.0(3) . . ?
O1 C18 N3 125.9(2) . . ?
O1 C18 C1 127.5(3) . . ?
N3 C18 C1 106.5(2) . . ?
O6 C19 N3 111.1(2) . . ?
O23 C19 O6 127.4(3) . . ?
O23 C19 N3 121.4(3) . . ?
C21 C20 O6 101.4(3) . . ?
C21 C20 C22 111.4(4) . . ?
C22 C20 O6 108.6(3) . . ?
C23 C20 O6 111.2(3) . . ?
C23 C20 C21 111.9(4) . . ?
C23 C20 C22 111.8(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C10 H10C O1 0.96 2.46 3.190(4) 132.5 2_458
C16 H16 O23 0.93 2.32 2.847(4) 115.2 .
C22 H22A O23 0.96 2.42 2.956(6) 115.0 .
C22 H22B O2 0.96 2.54 3.457(4) 160.5 2_548
C23 H23C O23 0.96 2.42 3.011(5) 119.6 .

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 C15 C16 C17 -179.1(2) . . . . ?
O2 C7 C8 C9 179.3(3) . . . . ?
C1 C2 C3 C4 -114.5(3) . . . . ?
C1 C3 C4 C5 97.8(3) . . . . ?
C1 C3 C4 C9 -88.3(4) . . . . ?
C1 C12 C13 C14 179.4(3) . . . . ?
C1 C12 C17 N3 1.2(3) . . . . ?
C1 C12 C17 C16 179.7(3) . . . . ?
C2 C1 C3 C4 114.4(3) . . . . ?
C2 C1 C12 C13 35.2(5) . . . . ?
C2 C1 C12 C17 -147.1(3) . . . . ?
C2 C1 C18 O1 -26.7(5) . . . . ?
C2 C1 C18 N3 151.3(3) . . . . ?
C2 C3 C4 C5 173.7(3) . . . . ?
C2 C3 C4 C9 -12.4(4) . . . . ?
C3 C1 C2 C11 113.0(3) . . . . ?
C3 C1 C12 C13 -36.3(5) . . . . ?
C3 C1 C12 C17 141.4(3) . . . . ?
C3 C1 C18 O1 39.8(4) . . . . ?
C3 C1 C18 N3 -142.2(2) . . . . ?
C3 C4 C5 C6 172.4(3) . . . . ?
C3 C4 C9 C8 -173.7(3) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C4 C9 C8 0.2(4) . . . . ?
C5 C6 C7 O2 179.3(3) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 -2.2(4) . . . . ?
C7 C8 C9 C4 1.8(4) . . . . ?
C9 C4 C5 C6 -1.8(4) . . . . ?
C10 O2 C7 C6 -177.4(3) . . . . ?
C10 O2 C7 C8 1.2(4) . . . . ?
C11 C2 C3 C1 -111.5(3) . . . . ?
C11 C2 C3 C4 134.0(3) . . . . ?
C12 C1 C2 C3 -107.6(3) . . . . ?
C12 C1 C2 C11 5.4(5) . . . . ?
C12 C1 C3 C2 117.1(3) . . . . ?
C12 C1 C3 C4 -128.5(3) . . . . ?
C12 C1 C18 O1 -176.3(3) . . . . ?
C12 C1 C18 N3 1.7(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C12 C17 N3 179.2(3) . . . . ?
C13 C12 C17 C16 -2.3(5) . . . . ?
C13 C14 C15 Cl1 178.7(3) . . . . ?
C13 C14 C15 C16 -2.2(5) . . . . ?
C14 C15 C16 C17 1.9(5) . . . . ?
C15 C16 C17 N3 178.6(3) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C17 N3 C18 O1 177.0(3) . . . . ?
C17 N3 C18 C1 -1.0(3) . . . . ?
C17 N3 C19 O6 -165.9(3) . . . . ?
C17 N3 C19 O23 12.3(5) . . . . ?
C17 C12 C13 C14 1.9(5) . . . . ?
C18 N3 C17 C12 -0.1(3) . . . . ?
C18 N3 C17 C16 -178.4(3) . . . . ?
C18 N3 C19 O6 22.9(5) . . . . ?
C18 N3 C19 O23 -158.9(3) . . . . ?
C18 C1 C2 C3 110.3(3) . . . . ?
C18 C1 C2 C11 -136.7(3) . . . . ?
C18 C1 C3 C2 -104.6(3) . . . . ?
C18 C1 C3 C4 9.7(4) . . . . ?
C18 C1 C12 C13 -179.5(3) . . . . ?
C18 C1 C12 C17 -1.8(3) . . . . ?
C19 O6 C20 C21 175.0(4) . . . . ?
C19 O6 C20 C22 57.5(4) . . . . ?
C19 O6 C20 C23 -65.9(4) . . . . ?
C19 N3 C17 C12 -172.6(3) . . . . ?
C19 N3 C17 C16 9.0(5) . . . . ?
C19 N3 C18 O1 -10.9(5) . . . . ?
C19 N3 C18 C1 171.1(3) . . . . ?
C20 O6 C19 O23 8.8(6) . . . . ?
C20 O6 C19 N3 -173.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-16
_olex2_submission_special_instructions 'No special instructions were received'
