# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_icrjdc
_database_code_depnum_ccdc_archive 'CCDC 1961691'
loop_
_audit_author_name
_audit_author_address
'Manuel de Pedro' 'University of Cantabria'
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_nottingham_internal_coll_name   ICRJDC
_nottingham_internal_coll_number 16550
_nottingham_internal_coll_client ICR/JDU
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 2.00
_nottingham_internal_coll_frame_width 2.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   17/10/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 08/02/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 8/2/2017
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 8/2/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 8/2/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 8/2/2017
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_vrf_PLAT112_icrjdc              
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.        B         92 %Fit  
RESPONSE: This is a psuedosymmetry, not a true missing symmetry element. 
The two moleucles differ in the orientation of the 2-methylbutyl chain.
;
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H19 N2, Cl'
_chemical_formula_sum            'C10 H19 Cl N2'
_chemical_formula_weight         202.72
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 N4 H24'
_chemical_oxdiff_usercomment     
'ICRJDC #16550 GVA-1082 IN FOMBLIN FILM ON MICROMOUNT FOR ICR/JDU'
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'

_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 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0742(3)
_cell_length_b                   10.8811(4)
_cell_length_c                   11.8127(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.664(3)
_cell_angle_gamma                90
_cell_volume                     1137.98(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5917
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6750
_cell_measurement_theta_min      4.0650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.635
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 6 0.2211
-1 3 -6 0.2211
-5 1 -3 0.2611
5 -1 3 0.2611
-6 0 0 0.2921
5 2 -5 0.4355
3 -5 -5 0.3659
-3 5 5 0.3659
-3 -6 0 0.3986
-4 -5 2 0.3972
-5 0 5 0.3628
3 6 0 0.4102
-1 6 4 0.4043
2 1 6 0.2016
1 1 7 0.2087
0 0 8 0.2332
3 2 5 0.2437
-2 -1 -6 0.1787
5 -3 1 0.2963
5 -2 0 0.3284
3 -5 4 0.3294
-1 -5 5 0.3146
-3 -4 6 0.3664
-5 2 0 0.3385
-1 3 7 0.2753
1 4 6 0.2789
3 4 3 0.3147
4 -1 -7 0.4173
0 -3 -7 0.2831
-5 -3 1 0.3652
-3 -4 -4 0.3336
3 -2 6 0.2033
-1 -2 7 0.2555
-5 0 -3 0.2398
1 2 -7 0.2973

_exptl_crystal_recrystallization_method 
'diffusion of ethyl acetate vapour into a acetonitrle solution of the compound'
_exptl_crystal_size_max          0.856
_exptl_crystal_size_mid          0.794
_exptl_crystal_size_min          0.38
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
1.0004 -2.9992 5.9926 0.8713 -0.2720 0.2861
-1.0004 2.9992 -5.9926 -0.8713 0.2720 -0.2861
-5.0003 1.0012 -2.9888 -0.9083 0.1781 0.4834
5.0003 -1.0012 2.9888 0.9083 -0.1781 -0.4834
-6.0000 0.0011 0.0101 -0.6399 0.1467 0.8113
4.9995 1.9990 -5.0037 -0.0966 0.0161 -1.0091
2.9976 -4.9897 -5.0009 -0.2076 -0.8859 -0.4864
-2.9976 4.9897 5.0009 0.2076 0.8859 0.4864
-3.0016 -5.9901 0.0046 -0.2322 -0.7417 0.6219
-4.0009 -4.9927 2.0045 -0.1133 -0.5280 0.8255
-4.9990 -0.0021 5.0038 0.0674 0.2556 0.9371
3.0016 5.9901 -0.0046 0.2322 0.7417 -0.6219
-0.9976 5.9884 3.9985 0.2861 0.9462 0.1278
2.0015 0.9944 5.9912 0.9194 0.2469 0.0068
1.0017 0.9940 6.9920 0.9329 0.2980 0.1942
0.0016 -0.0049 7.9927 0.9610 0.2133 0.4176
3.0015 1.9933 4.9905 0.8914 0.3316 -0.2167
-2.0015 -0.9944 -5.9912 -0.9194 -0.2469 -0.0068
4.9994 -2.9969 0.9904 0.6973 -0.5031 -0.5157
4.9995 -1.9978 -0.0086 0.5625 -0.3940 -0.6040
2.9995 -4.9953 3.9909 0.8736 -0.6459 -0.0166
-1.0003 -4.9951 4.9967 0.5671 -0.5214 0.5764
-2.9998 -3.9969 5.9992 0.4593 -0.3100 0.8630
-4.9995 1.9978 0.0086 -0.5625 0.3940 0.6040
-0.9978 2.9912 6.9955 0.6904 0.6186 0.3925
1.0023 3.9899 5.9931 0.7689 0.6789 0.0338
3.0017 3.9914 2.9925 0.6219 0.5500 -0.3932
3.9983 -0.9949 -7.0004 -0.3996 -0.4203 -0.8702
-0.0022 -2.9911 -6.9938 -0.7970 -0.5942 -0.2573
-5.0006 -2.9950 1.0073 -0.3693 -0.2586 0.8364
-3.0019 -3.9908 -3.9916 -0.7420 -0.5767 0.3410
3.0007 -2.0011 5.9893 1.0700 -0.1851 -0.0203
-0.9991 -2.0010 6.9951 0.7635 -0.0606 0.5727
-5.0006 0.0028 -2.9888 -0.8937 0.0423 0.5194
0.9991 2.0010 -6.9951 -0.7635 0.0606 -0.5727

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.866
_diffrn_reflns_theta_min         3.835
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -22.00   2.00    2.00    --  -43.31 -38.00  30.00   46
  2  ω    -50.00  26.00   2.00    2.00    --  -43.31  38.00-150.00   38
  3  ω    -20.00  82.00   2.00    2.00    --   43.31 -99.00-150.00   51
  4  ω     35.00  97.00   2.00    2.00    --  103.95 -45.00 150.00   31
  5  ω     31.00  91.00   2.00    2.00    --  103.95 -30.00 -60.00   30
  6  ω     35.00  97.00   2.00    2.00    --  103.95 -45.00  60.00   31
  7  ω     31.00  91.00   2.00    2.00    --  103.95 -30.00 -90.00   30
  8  ω     35.00  97.00   2.00    2.00    --  103.95 -45.00  90.00   31
  9  ω     23.00 107.00   2.00    2.00    --  103.95 -94.00  90.00   42
 10  ω     35.00  97.00   2.00    2.00    --  103.95 -45.00-150.00   31
 11  ω     31.00  91.00   2.00    2.00    --  103.95 -30.00 120.00   30
 12  ω     23.00 107.00   2.00    2.00    --  103.95 -94.00  60.00   42
 13  ω     35.00  89.00   2.00    2.00    --  103.95 -45.00-120.00   27
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1068545000
_diffrn_orient_matrix_UB_12      -0.0146813000
_diffrn_orient_matrix_UB_13      0.1202055000
_diffrn_orient_matrix_UB_21      -0.0243880000
_diffrn_orient_matrix_UB_22      0.1360557000
_diffrn_orient_matrix_UB_23      0.0267787000
_diffrn_orient_matrix_UB_31      -0.1351280000
_diffrn_orient_matrix_UB_32      -0.0360669000
_diffrn_orient_matrix_UB_33      0.0522557000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3508
_reflns_number_total             3541
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.033(14)
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.063
_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)+(0.0635P)²+0.0992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0889
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.967(14) 0.033(14)
2. 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
3.a Ternary CH refined with riding coordinates:
 C7(H7), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C26(H26A,H26B), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_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
N1 N 0.1286(2) 0.51520(18) 0.37808(14) 0.0141(4) Uani 1 1 d . . . . .
C2 C 0.0943(2) 0.4348(2) 0.29042(18) 0.0154(4) Uani 1 1 d . . . . .
N3 N 0.2210(2) 0.37348(18) 0.28633(15) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.3378(2) 0.4156(2) 0.37334(18) 0.0164(4) Uani 1 1 d . . . . .
H4 H 0.439302 0.387196 0.389668 0.020 Uiso 1 1 calc R . . . .
C5 C 0.2805(2) 0.5046(2) 0.43073(18) 0.0155(4) Uani 1 1 d . . . . .
H5 H 0.333886 0.551086 0.494808 0.019 Uiso 1 1 calc R . . . .
C6 C 0.0221(2) 0.6023(2) 0.41310(18) 0.0172(4) Uani 1 1 d . . . . .
H6A H -0.038602 0.642533 0.343063 0.021 Uiso 1 1 calc R . . . .
H6B H 0.079926 0.666917 0.462848 0.021 Uiso 1 1 calc R . . . .
C7 C -0.0840(2) 0.5389(2) 0.4791(2) 0.0187(5) Uani 1 1 d . . . . .
H7 H -0.138938 0.471696 0.429468 0.022 Uiso 1 1 calc R . . . .
C8 C 0.0039(3) 0.4829(3) 0.5923(2) 0.0283(6) Uani 1 1 d . . . . .
H8A H 0.059016 0.547822 0.641613 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.075638 0.422050 0.575300 0.042 Uiso 1 1 calc GR . . . .
H8C H -0.066565 0.442883 0.632754 0.042 Uiso 1 1 calc GR . . . .
C9 C -0.1993(3) 0.6357(3) 0.4981(2) 0.0280(6) Uani 1 1 d . . . . .
H9A H -0.146566 0.699685 0.551542 0.034 Uiso 1 1 calc R . . . .
H9B H -0.243402 0.675727 0.423058 0.034 Uiso 1 1 calc R . . . .
C10 C -0.3260(3) 0.5818(3) 0.5480(3) 0.0362(6) Uani 1 1 d . . . . .
H10A H -0.286180 0.557318 0.628703 0.054 Uiso 1 1 calc GR . . . .
H10B H -0.368215 0.509799 0.502382 0.054 Uiso 1 1 calc GR . . . .
H10C H -0.405338 0.643629 0.544941 0.054 Uiso 1 1 calc GR . . . .
C11 C -0.0563(2) 0.4174(2) 0.2126(2) 0.0224(5) Uani 1 1 d . . . . .
H11A H -0.118238 0.364580 0.250801 0.034 Uiso 1 1 calc GR . . . .
H11B H -0.044523 0.378745 0.140207 0.034 Uiso 1 1 calc GR . . . .
H11C H -0.105802 0.497396 0.195455 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.2339(3) 0.2751(2) 0.2038(2) 0.0244(5) Uani 1 1 d . . . . .
H12A H 0.336807 0.241926 0.222080 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.211604 0.308338 0.124799 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.161956 0.209501 0.209605 0.037 Uiso 1 1 calc GR . . . .
N21 N 0.60381(18) 0.50823(19) 0.87735(14) 0.0145(4) Uani 1 1 d . . . . .
C22 C 0.5621(2) 0.4247(2) 0.79317(17) 0.0161(4) Uani 1 1 d . . . . .
N23 N 0.6868(2) 0.36536(19) 0.78181(16) 0.0185(4) Uani 1 1 d . . . . .
C24 C 0.8104(2) 0.4119(2) 0.86017(19) 0.0193(4) Uani 1 1 d . . . . .
H24 H 0.912247 0.385543 0.869915 0.023 Uiso 1 1 calc R . . . .
C25 C 0.7591(2) 0.5020(2) 0.92012(19) 0.0178(4) Uani 1 1 d . . . . .
H25 H 0.817519 0.551323 0.979784 0.021 Uiso 1 1 calc R . . . .
C26 C 0.5000(2) 0.5895(2) 0.92264(18) 0.0178(4) Uani 1 1 d . . . . .
H26A H 0.422538 0.622153 0.857166 0.021 Uiso 1 1 calc R . . . .
H26B H 0.557248 0.659973 0.963427 0.021 Uiso 1 1 calc R . . . .
C27 C 0.4220(2) 0.5202(2) 1.00676(19) 0.0196(5) Uani 1 1 d . . . . .
H27 H 0.374383 0.444180 0.967193 0.023 Uiso 1 1 calc R . . . .
C28 C 0.5374(3) 0.4821(3) 1.1160(2) 0.0337(6) Uani 1 1 d . . . . .
H28A H 0.590137 0.555243 1.152952 0.051 Uiso 1 1 calc GR . . . .
H28B H 0.610784 0.425322 1.094850 0.051 Uiso 1 1 calc GR . . . .
H28C H 0.485357 0.441519 1.170133 0.051 Uiso 1 1 calc GR . . . .
C29 C 0.2980(3) 0.6005(3) 1.0364(2) 0.0291(6) Uani 1 1 d . . . . .
H29A H 0.265192 0.564150 1.103664 0.035 Uiso 1 1 calc R . . . .
H29B H 0.340440 0.682810 1.059920 0.035 Uiso 1 1 calc R . . . .
C30 C 0.1612(3) 0.6154(3) 0.9374(3) 0.0396(7) Uani 1 1 d . . . . .
H30A H 0.082225 0.660463 0.964813 0.059 Uiso 1 1 calc GR . . . .
H30B H 0.123076 0.534180 0.909364 0.059 Uiso 1 1 calc GR . . . .
H30C H 0.189887 0.661177 0.874122 0.059 Uiso 1 1 calc GR . . . .
C31 C 0.4065(3) 0.4038(3) 0.7253(2) 0.0241(5) Uani 1 1 d . . . . .
H31A H 0.410352 0.363708 0.651735 0.036 Uiso 1 1 calc GR . . . .
H31B H 0.354067 0.482764 0.709689 0.036 Uiso 1 1 calc GR . . . .
H31C H 0.352091 0.351063 0.769639 0.036 Uiso 1 1 calc GR . . . .
C32 C 0.6945(3) 0.2662(2) 0.6998(2) 0.0279(6) Uani 1 1 d . . . . .
H32A H 0.794896 0.228365 0.718967 0.042 Uiso 1 1 calc GR . . . .
H32B H 0.675872 0.299564 0.620854 0.042 Uiso 1 1 calc GR . . . .
H32C H 0.617794 0.204094 0.704483 0.042 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.85608(5) 0.74295(5) 0.12174(4) 0.02099(16) Uani 1 1 d . . . . .
Cl2 Cl 0.33460(5) 0.74391(5) 0.63739(4) 0.01983(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.339(3) . ?
N1 C5 1.387(3) . ?
N1 C6 1.476(3) . ?
C2 N3 1.339(3) . ?
C2 C11 1.483(3) . ?
N3 C4 1.383(3) . ?
N3 C12 1.469(3) . ?
C4 C5 1.351(3) . ?
C6 C7 1.529(3) . ?
C7 C8 1.526(3) . ?
C7 C9 1.535(3) . ?
C9 C10 1.519(4) . ?
N21 C22 1.339(3) . ?
N21 C25 1.390(3) . ?
N21 C26 1.475(3) . ?
C22 N23 1.335(3) . ?
C22 C31 1.481(3) . ?
N23 C24 1.385(3) . ?
N23 C32 1.462(3) . ?
C24 C25 1.350(3) . ?
C26 C27 1.538(3) . ?
C27 C28 1.530(3) . ?
C27 C29 1.525(3) . ?
C29 C30 1.516(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.37(19) . . ?
C2 N1 C6 125.54(18) . . ?
C5 N1 C6 125.08(18) . . ?
N1 C2 C11 126.1(2) . . ?
N3 C2 N1 107.34(18) . . ?
N3 C2 C11 126.6(2) . . ?
C2 N3 C4 109.42(19) . . ?
C2 N3 C12 125.51(18) . . ?
C4 N3 C12 125.07(19) . . ?
C5 C4 N3 107.08(19) . . ?
C4 C5 N1 106.79(19) . . ?
N1 C6 C7 112.19(19) . . ?
C6 C7 C9 106.9(2) . . ?
C8 C7 C6 111.13(18) . . ?
C8 C7 C9 112.8(2) . . ?
C10 C9 C7 113.0(2) . . ?
C22 N21 C25 109.59(19) . . ?
C22 N21 C26 125.27(18) . . ?
C25 N21 C26 125.05(19) . . ?
N21 C22 C31 125.9(2) . . ?
N23 C22 N21 107.19(18) . . ?
N23 C22 C31 126.9(2) . . ?
C22 N23 C24 109.6(2) . . ?
C22 N23 C32 126.0(2) . . ?
C24 N23 C32 124.3(2) . . ?
C25 C24 N23 107.09(19) . . ?
C24 C25 N21 106.5(2) . . ?
N21 C26 C27 111.16(19) . . ?
C28 C27 C26 110.52(18) . . ?
C29 C27 C26 109.5(2) . . ?
C29 C27 C28 111.4(2) . . ?
C30 C29 C27 113.9(2) . . ?

_olex2_date_sample_data_collection 2016-10-17
_olex2_date_sample_submission    2016-10-13
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.456
_oxdiff_exptl_absorpt_empirical_full_min 0.579
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.967(14)
2 0.033(14)

####################################################################### 
# 
# 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_icrjda
_database_code_depnum_ccdc_archive 'CCDC 1962239'
loop_
_audit_author_name
_audit_author_address
'Manuel de Pedro'
;University of Cantabria
Spain
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_nottingham_internal_coll_name   ICRJDA
_nottingham_internal_coll_number 16483
_nottingham_internal_coll_client ICR/JDU
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 2.00'
_nottingham_internal_coll_frame_width 'in, 2.00'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   12/09/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 13/09/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 13/9/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 8/2/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 8/2/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 8/2/2017
_refine_special_details          ?
_audit_creation_date             2017-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H29 N2 O, Cl, H2 O'
_chemical_formula_sum            'C16 H31 Cl N2 O2'
_chemical_formula_weight         318.88
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H31 Cl N2 O2'
_chemical_oxdiff_usercomment     
'ICRJDA #16483 GVB-1152 micromount in fomblin for ICR/JDU'
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'
Cl Cl 0.3639 0.7018 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.6283(2)
_cell_length_b                   7.8369(3)
_cell_length_c                   17.6060(5)
_cell_angle_alpha                90.888(3)
_cell_angle_beta                 94.947(3)
_cell_angle_gamma                91.100(3)
_cell_volume                     910.84(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30840
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6660
_cell_measurement_theta_min      5.0220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 1 0.1380
4 0 -1 0.1200
0 5 -2 0.2420
-1 -2 1 0.1987
1 -5 2 0.2506
0 0 -1 0.0268
0 0 1 0.0308
-4 -3 2 0.1721
4 3 -2 0.1984
2 -4 0 0.2476
-4 1 1 0.1766
-2 -3 -7 0.1509
-3 0 9 0.1047
3 0 -9 0.0863
0 3 10 0.1353

_exptl_crystal_recrystallization_method 
'Crystallised from acetonitrile at 4 degree celcius'
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.058
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
-3.9997 0.0004 1.0425 0.4917 0.0093 0.7891
3.9997 -0.0004 -1.0425 -0.4917 -0.0093 -0.7891
0.0004 4.9957 -2.0271 0.8318 0.0596 -0.5434
-1.0001 -1.9982 1.0215 -0.2095 -0.0172 0.4143
0.9995 -4.9957 2.0162 -0.9563 -0.0838 0.3477
0.0001 -0.0006 -0.9989 0.0065 0.0873 -0.0063
-0.0001 0.0006 0.9989 -0.0065 -0.0873 0.0063
-3.9999 -2.9972 2.0590 -0.0061 -0.0090 1.1139
3.9999 2.9972 -2.0590 0.0061 0.0090 -1.1139
1.9996 -3.9974 0.0017 -0.9042 0.0436 0.0333
-3.9996 0.9998 1.0366 0.6555 -0.0137 0.6830
-1.9991 -3.0024 -6.9526 -0.1968 0.7282 0.6658
-3.0006 0.0052 9.0225 0.3153 -0.7131 0.6438
3.0006 -0.0052 -9.0225 -0.3153 0.7131 -0.6438
-0.0010 3.0041 9.9710 0.4265 -0.9417 -0.2555

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49890
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.944
_diffrn_reflns_theta_min         5.044
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  -6.00   2.00    2.00    --  -38.50 -83.00 -29.99   17
  2  ω   -111.00 -17.00   2.00    2.00    --  -38.50 -38.00 -60.00   47
  3  ω     16.00 112.00   2.00    2.00    --   42.83  57.00  30.00   48
  4  ω    -27.00  69.00   2.00    2.00    --   42.83 -57.00 -30.00   48
  5  ω      2.00  98.00   2.00    2.00    --   42.83-125.00-120.00   48
  6  ω     14.00  46.00   2.00    2.00    --   46.00  79.00 -72.14   16
  7  ω     14.00  46.00   2.00    2.00    --   46.00  79.00  59.81   16
  8  ω     18.00  46.00   2.00    2.00    --   50.00  79.00 169.04   14
  9  ω     18.00  46.00   2.00    2.00    --   50.00  80.00 132.69   14
 10  ω     22.00  48.00   2.00    2.00    --   54.00  78.00 -55.35   13
 11  ω     24.00 126.00   2.00    2.00    --   54.00  72.00  37.36   51
 12  ω     23.00 127.00   2.00    2.00    --   54.00  77.00  77.81   52
 13  ω     31.00 135.00   2.00    2.00    --   62.00  76.00  81.37   52
 14  ω     31.00 135.00   2.00    2.00    --   62.00  75.00-147.23   52
 15  ω     36.00 138.00   2.00    2.00    --   66.00  72.00-118.29   51
 16  ω     35.00 139.00   2.00    2.00    --   66.00  74.00 146.52   52
 17  ω     35.00 139.00   2.00    2.00    --   66.00  77.00  88.05   52
 18  ω     39.00 143.00   2.00    2.00    --   70.00  77.00 -91.28   52
 19  ω     39.00 143.00   2.00    2.00    --   70.00  76.00 -26.89   52
 20  ω     44.00 146.00   2.00    2.00    --   74.00  73.00  14.04   51
 21  ω     43.00 147.00   2.00    2.00    --   74.00  76.00 -48.51   52
 22  ω     44.00 146.00   2.00    2.00    --   74.00  70.00-144.31   51
 23  ω     47.00 151.00   2.00    2.00    --   78.00  77.00 158.11   52
 24  ω     51.00 155.00   2.00    2.00    --   82.00  76.00  55.53   52
 25  ω     53.00 153.00   2.00    2.00    --   82.00  68.00 -84.75   50
 26  ω     57.00 157.00   2.00    2.00    --   86.00  67.00 -11.35   50
 27  ω     57.00 157.00   2.00    2.00    --   86.00  69.00 103.15   50
 28  ω     73.00 177.00   2.00    2.00    --  104.50  77.00  60.00   52
 29  ω     33.00 121.00   2.00    2.00    --  104.50-125.00  90.00   44
 30  ω     80.00 176.00   2.00    2.00    --  104.50  45.00  30.00   48
 31  ω     77.00 175.00   2.00    2.00    --  104.50  61.00 150.00   49
 32  ω     73.00 177.00   2.00    2.00    --  104.50  77.00-120.00   52
 33  ω     33.00  97.00   2.00    2.00    --  104.50 -45.00 150.00   32
 34  ω     73.00 177.00   2.00    2.00    --  104.50  77.00-180.00   52
 35  ω     33.00  97.00   2.00    2.00    --  104.50 -45.00 -60.00   32
 36  ω     23.00 109.00   2.00    2.00    --  104.50 -94.00 120.00   43
 37  ω     23.00 109.00   2.00    2.00    --  104.50 -94.00 -90.00   43
 38  ω     73.00 177.00   2.00    2.00    --  104.50  77.00 120.00   52
 39  ω     73.00 177.00   2.00    2.00    --  104.50  77.00  30.00   52
 40  ω     73.00 177.00   2.00    2.00    --  104.50  77.00-150.00   52
 41  ω     77.00 175.00   2.00    2.00    --  104.50  59.00 -50.10   49
 42  ω     73.00 177.00   2.00    2.00    --  104.50  77.00 -90.00   52
 43  ω     80.00 176.00   2.00    2.00    --  104.50  45.00   0.00   48
 44  ω     77.00 175.00   2.00    2.00    --  104.50  61.00-180.00   49
 45  ω     73.00 177.00   2.00    2.00    --  104.50  77.00  90.00   52
 46  ω     23.00 109.00   2.00    2.00    --  104.50 -94.00-180.00   43
 47  ω    -50.00  34.00   2.00    2.00    --  -38.50  38.00  90.00   42
 48  ω    -45.00  -7.00   2.00    2.00    --  -38.50 -82.00 -92.00   19
 49  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00 -30.00   86
 50  ω     20.00 114.00   2.00    2.00    --   42.83  38.00  60.00   47
 51  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00-180.00   86
 52  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00-150.00   86
 53  ω     16.00 112.00   2.00    2.00    --   42.83  57.00-180.00   48
 54  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00-120.00   86
 55  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00 -90.00   86
 56  ω    -44.00 128.00   2.00    2.00    --   42.83   0.00 -60.00   86
 57  ω     13.00  39.00   2.00    2.00    --   46.00  83.00-112.72   13
 58  ω     22.00  48.00   2.00    2.00    --   54.00  78.00 -15.46   13
 59  ω     27.00 131.00   2.00    2.00    --   58.00  74.00-166.88   52
 60  ω     39.00 143.00   2.00    2.00    --   70.00  77.00 -42.62   52
 61  ω     43.00 147.00   2.00    2.00    --   74.00  77.00 -99.98   52
 62  ω     46.00 144.00   2.00    2.00    --   74.00  63.00  43.57   49
 63  ω     33.00  97.00   2.00    2.00    --  104.50 -45.00-120.00   32
 64  ω     18.00 178.00   2.00    2.00    --  104.50   0.00 -60.00   80
 65  ω     18.00 178.00   2.00    2.00    --  104.50   0.00 -90.00   80
 66  ω     18.00 178.00   2.00    2.00    --  104.50   0.00-120.00   80
 67  ω     18.00 178.00   2.00    2.00    --  104.50   0.00-150.00   80
 68  ω     18.00 178.00   2.00    2.00    --  104.50   0.00-180.00   80
 69  ω     73.00 177.00   2.00    2.00    --  104.50  77.00 150.00   52
 70  ω     77.00 175.00   2.00    2.00    --  104.50  61.00  60.00   49
 71  ω     77.00 175.00   2.00    2.00    --  104.50  61.00  30.00   49
 72  ω     77.00 175.00   2.00    2.00    --  104.50  61.00 -30.00   49
 73  ω     77.00 175.00   2.00    2.00    --  104.50  61.00-120.00   49
 74  ω     18.00 162.00   2.00    2.00    --  104.50   0.00  90.00   72
 75  ω     18.00 178.00   2.00    2.00    --  104.50   0.00 -30.00   80
 76  ω     18.00 178.00   2.00    2.00    --  104.50   0.00   0.00   80
 77  ω     74.00 178.00   2.00    2.00    --  104.50  78.00-161.68   52
 78  ω     18.00 178.00   2.00    2.00    --  104.50   0.00  60.00   80
 79  ω     18.00 178.00   2.00    2.00    --  104.50   0.00  30.00   80
 80  ω     77.00 175.00   2.00    2.00    --  104.50  61.00 120.00   49
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1246433000
_diffrn_orient_matrix_UB_12      0.1638302000
_diffrn_orient_matrix_UB_13      -0.0065961000
_diffrn_orient_matrix_UB_21      -0.0251016000
_diffrn_orient_matrix_UB_22      -0.0235130000
_diffrn_orient_matrix_UB_23      -0.0873656000
_diffrn_orient_matrix_UB_31      -0.1956536000
_diffrn_orient_matrix_UB_32      -0.1061865000
_diffrn_orient_matrix_UB_33      0.0063491000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                6812
_reflns_number_total             6939
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 3161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6939
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.040
_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)+(0.0768P)²+0.2292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1119
_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, All O(H,H) groups
2. Restrained distances
 O2W-H2WA = O2W-H2WB = O1W-H1WB = O1W-H1WA
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C28(H28), C29(H29), C32(H32), C34(H34)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C26(H26A,H26B),
 C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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_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
N1 N 0.8470(4) 1.0203(3) 0.81313(14) 0.0235(5) Uani 1 1 d . . . . .
C2 C 0.9532(5) 1.1668(4) 0.82420(16) 0.0240(6) Uani 1 1 d . . . . .
N3 N 0.8446(4) 1.2733(3) 0.86323(14) 0.0237(5) Uani 1 1 d . . . . .
C4 C 0.6654(5) 1.1919(4) 0.87783(18) 0.0285(7) Uani 1 1 d . . . . .
H4 H 0.561287 1.238539 0.905133 0.034 Uiso 1 1 calc R . . . .
C5 C 0.6658(5) 1.0349(4) 0.84635(17) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.561710 0.949989 0.846746 0.032 Uiso 1 1 calc R . . . .
C6 C 0.9075(5) 0.8686(4) 0.77031(17) 0.0273(7) Uani 1 1 d . . . . .
H6A H 1.054301 0.851031 0.781988 0.033 Uiso 1 1 calc R . . . .
H6B H 0.834169 0.766670 0.787182 0.033 Uiso 1 1 calc R . . . .
O7 O 0.8664(3) 0.8852(3) 0.69215(11) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.6617(4) 0.8391(3) 0.66261(14) 0.0204(5) Uani 1 1 d . . . . .
H8 H 0.592694 0.776224 0.702387 0.024 Uiso 1 1 calc R . . . .
C9 C 0.6705(4) 0.7237(3) 0.59234(15) 0.0232(6) Uani 1 1 d . . . . .
H9 H 0.729177 0.793748 0.552328 0.028 Uiso 1 1 calc R . . . .
C10 C 0.4516(5) 0.6756(4) 0.56245(18) 0.0311(7) Uani 1 1 d . . . . .
H10A H 0.453147 0.600452 0.516800 0.037 Uiso 1 1 calc R . . . .
H10B H 0.386041 0.611478 0.601952 0.037 Uiso 1 1 calc R . . . .
C11 C 0.3293(5) 0.8336(4) 0.54190(17) 0.0327(7) Uani 1 1 d . . . . .
H11A H 0.188115 0.798274 0.524986 0.039 Uiso 1 1 calc R . . . .
H11B H 0.387210 0.891256 0.498855 0.039 Uiso 1 1 calc R . . . .
C12 C 0.3284(5) 0.9595(4) 0.60920(17) 0.0299(7) Uani 1 1 d . . . . .
H12 H 0.255022 0.903860 0.649830 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5455(5) 1.0001(4) 0.64192(16) 0.0241(6) Uani 1 1 d . . . . .
H13A H 0.616943 1.064316 0.603956 0.029 Uiso 1 1 calc R . . . .
H13B H 0.542553 1.073636 0.688018 0.029 Uiso 1 1 calc R . . . .
C14 C 0.8085(5) 0.5690(4) 0.60641(17) 0.0288(6) Uani 1 1 d . . . . .
H14 H 0.944487 0.614380 0.627274 0.035 Uiso 1 1 calc R . . . .
C15 C 0.7348(7) 0.4454(4) 0.6648(2) 0.0418(8) Uani 1 1 d . . . . .
H15A H 0.718405 0.507499 0.712572 0.063 Uiso 1 1 calc GR . . . .
H15B H 0.834206 0.355562 0.674273 0.063 Uiso 1 1 calc GR . . . .
H15C H 0.604457 0.393939 0.645081 0.063 Uiso 1 1 calc GR . . . .
C16 C 0.8378(6) 0.4751(5) 0.5315(2) 0.0429(9) Uani 1 1 d . . . . .
H16A H 0.709706 0.419744 0.511715 0.064 Uiso 1 1 calc GR . . . .
H16B H 0.941561 0.388623 0.540429 0.064 Uiso 1 1 calc GR . . . .
H16C H 0.880820 0.556950 0.494228 0.064 Uiso 1 1 calc GR . . . .
C17 C 0.2172(6) 1.1212(5) 0.5857(2) 0.0410(8) Uani 1 1 d . . . . .
H17A H 0.282507 1.174642 0.543911 0.062 Uiso 1 1 calc GR . . . .
H17B H 0.221667 1.200836 0.629263 0.062 Uiso 1 1 calc GR . . . .
H17C H 0.075871 1.092143 0.568639 0.062 Uiso 1 1 calc GR . . . .
C18 C 1.1581(6) 1.2018(5) 0.8001(2) 0.0426(9) Uani 1 1 d . . . . .
H18A H 1.161113 1.313513 0.775919 0.064 Uiso 1 1 calc GR . . . .
H18B H 1.191748 1.113226 0.763627 0.064 Uiso 1 1 calc GR . . . .
H18C H 1.257164 1.201836 0.844751 0.064 Uiso 1 1 calc GR . . . .
C19 C 0.9033(5) 1.4485(4) 0.88831(18) 0.0278(7) Uani 1 1 d . . . . .
H19A H 0.782729 1.519248 0.886352 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.999743 1.495684 0.854614 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.966618 1.447304 0.940699 0.042 Uiso 1 1 calc GR . . . .
N21 N 0.7239(4) 0.2583(3) 0.11262(13) 0.0231(5) Uani 1 1 d . . . . .
C22 C 0.6117(5) 0.1140(4) 0.10267(17) 0.0258(7) Uani 1 1 d . . . . .
N23 N 0.7102(4) 0.0086(3) 0.05889(14) 0.0258(6) Uani 1 1 d . . . . .
C24 C 0.8869(5) 0.0876(4) 0.04055(17) 0.0276(7) Uani 1 1 d . . . . .
H24 H 0.984269 0.040550 0.010100 0.033 Uiso 1 1 calc R . . . .
C25 C 0.8958(5) 0.2439(4) 0.07386(17) 0.0258(7) Uani 1 1 d . . . . .
H25 H 1.000039 0.327904 0.071230 0.031 Uiso 1 1 calc R . . . .
C26 C 0.6858(5) 0.4028(4) 0.16386(17) 0.0250(6) Uani 1 1 d . . . . .
H26A H 0.778971 0.499231 0.154865 0.030 Uiso 1 1 calc R . . . .
H26B H 0.545248 0.441443 0.152578 0.030 Uiso 1 1 calc R . . . .
O27 O 0.7147(3) 0.3548(3) 0.24036(11) 0.0230(4) Uani 1 1 d . . . . .
C28 C 0.9243(4) 0.3255(3) 0.26680(14) 0.0191(5) Uani 1 1 d . . . . .
H28 H 0.989851 0.263010 0.225835 0.023 Uiso 1 1 calc R . . . .
C29 C 0.9279(4) 0.2133(3) 0.33718(15) 0.0223(6) Uani 1 1 d . . . . .
H29 H 0.873851 0.282779 0.378723 0.027 Uiso 1 1 calc R . . . .
C30 C 1.1504(5) 0.1778(4) 0.36250(17) 0.0290(6) Uani 1 1 d . . . . .
H30A H 1.157129 0.107880 0.408978 0.035 Uiso 1 1 calc R . . . .
H30B H 1.209762 0.111268 0.321959 0.035 Uiso 1 1 calc R . . . .
C31 C 1.2750(5) 0.3421(4) 0.37896(17) 0.0305(6) Uani 1 1 d . . . . .
H31A H 1.225107 0.402633 0.423198 0.037 Uiso 1 1 calc R . . . .
H31B H 1.418324 0.313427 0.392448 0.037 Uiso 1 1 calc R . . . .
C32 C 1.2621(5) 0.4596(4) 0.31042(16) 0.0271(6) Uani 1 1 d . . . . .
H32 H 1.322915 0.399325 0.267697 0.033 Uiso 1 1 calc R . . . .
C33 C 1.0397(5) 0.4921(4) 0.28475(15) 0.0233(6) Uani 1 1 d . . . . .
H33A H 0.976897 0.554772 0.325602 0.028 Uiso 1 1 calc R . . . .
H33B H 1.031699 0.563927 0.238855 0.028 Uiso 1 1 calc R . . . .
C34 C 0.7928(5) 0.0515(4) 0.32553(17) 0.0300(7) Uani 1 1 d . . . . .
H34 H 0.653931 0.088616 0.306959 0.036 Uiso 1 1 calc R . . . .
C35 C 0.8619(6) -0.0724(4) 0.26624(19) 0.0368(8) Uani 1 1 d . . . . .
H35A H 0.874893 -0.012529 0.218390 0.055 Uiso 1 1 calc GR . . . .
H35B H 0.762137 -0.166073 0.257519 0.055 Uiso 1 1 calc GR . . . .
H35C H 0.993323 -0.118471 0.284587 0.055 Uiso 1 1 calc GR . . . .
C36 C 0.7757(7) -0.0386(5) 0.4018(2) 0.0479(10) Uani 1 1 d . . . . .
H36A H 0.904965 -0.091172 0.418040 0.072 Uiso 1 1 calc GR . . . .
H36B H 0.668699 -0.126970 0.395515 0.072 Uiso 1 1 calc GR . . . .
H36C H 0.742534 0.045052 0.440582 0.072 Uiso 1 1 calc GR . . . .
C37 C 1.3804(6) 0.6258(5) 0.3272(2) 0.0385(7) Uani 1 1 d . . . . .
H37A H 1.373362 0.695345 0.281317 0.058 Uiso 1 1 calc GR . . . .
H37B H 1.522190 0.600960 0.342811 0.058 Uiso 1 1 calc GR . . . .
H37C H 1.322058 0.688436 0.368402 0.058 Uiso 1 1 calc GR . . . .
C38 C 0.4168(5) 0.0803(5) 0.1354(2) 0.0374(8) Uani 1 1 d . . . . .
H38A H 0.350794 -0.021661 0.110883 0.056 Uiso 1 1 calc GR . . . .
H38B H 0.328749 0.178446 0.126765 0.056 Uiso 1 1 calc GR . . . .
H38C H 0.441781 0.061948 0.190342 0.056 Uiso 1 1 calc GR . . . .
C39 C 0.6488(6) -0.1672(4) 0.0359(2) 0.0340(8) Uani 1 1 d . . . . .
H39A H 0.532305 -0.202706 0.063003 0.051 Uiso 1 1 calc GR . . . .
H39B H 0.761663 -0.243609 0.048590 0.051 Uiso 1 1 calc GR . . . .
H39C H 0.611485 -0.172573 -0.019171 0.051 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.39379(9) 0.64473(8) 0.82820(4) 0.03007(18) Uani 1 1 d . . . . .
Cl2 Cl 0.17334(10) 0.63154(8) 1.09680(4) 0.0343(2) Uani 1 1 d . . . . .
O2W O 0.1387(5) 0.8416(4) 0.94328(16) 0.0503(8) Uani 1 1 d D . . . .
H2WA H 0.228(7) 0.794(7) 0.916(3) 0.075 Uiso 1 1 d DR . . . .
H2WB H 0.157(9) 0.779(7) 0.983(2) 0.075 Uiso 1 1 d DR . . . .
O1W O 0.4197(6) 0.4291(4) 0.98135(16) 0.0552(9) Uani 1 1 d D . . . .
H1WA H 0.418(10) 0.492(7) 0.942(3) 0.083 Uiso 1 1 d DR . . . .
H1WB H 0.354(9) 0.479(8) 1.016(3) 0.083 Uiso 1 1 d DR . . . .


_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
N1 C2 1.337(4) . ?
N1 C5 1.386(4) . ?
N1 C6 1.478(4) . ?
C2 N3 1.334(4) . ?
C2 C18 1.479(5) . ?
N3 C4 1.383(5) . ?
N3 C19 1.470(4) . ?
C4 C5 1.341(5) . ?
C6 O7 1.388(4) . ?
O7 C8 1.448(3) . ?
C8 C9 1.527(4) . ?
C8 C13 1.523(3) . ?
C9 C10 1.538(4) . ?
C9 C14 1.543(4) . ?
C10 C11 1.524(4) . ?
C11 C12 1.531(4) . ?
C12 C13 1.529(4) . ?
C12 C17 1.523(4) . ?
C14 C15 1.528(5) . ?
C14 C16 1.529(4) . ?
N21 C22 1.343(4) . ?
N21 C25 1.383(4) . ?
N21 C26 1.476(4) . ?
C22 N23 1.338(4) . ?
C22 C38 1.480(5) . ?
N23 C24 1.379(5) . ?
N23 C39 1.470(4) . ?
C24 C25 1.348(5) . ?
C26 O27 1.402(3) . ?
O27 C28 1.450(3) . ?
C28 C29 1.529(3) . ?
C28 C33 1.516(4) . ?
C29 C30 1.536(4) . ?
C29 C34 1.539(4) . ?
C30 C31 1.527(4) . ?
C31 C32 1.527(4) . ?
C32 C33 1.532(4) . ?
C32 C37 1.520(4) . ?
C34 C35 1.520(5) . ?
C34 C36 1.539(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.9(3) . . ?
C2 N1 C6 126.1(3) . . ?
C5 N1 C6 124.9(3) . . ?
N1 C2 C18 126.1(3) . . ?
N3 C2 N1 107.8(3) . . ?
N3 C2 C18 126.1(3) . . ?
C2 N3 C4 109.0(3) . . ?
C2 N3 C19 126.5(3) . . ?
C4 N3 C19 124.5(3) . . ?
C5 C4 N3 107.4(3) . . ?
C4 C5 N1 106.9(3) . . ?
O7 C6 N1 112.1(2) . . ?
C6 O7 C8 115.3(2) . . ?
O7 C8 C9 108.8(2) . . ?
O7 C8 C13 109.5(2) . . ?
C13 C8 C9 110.4(2) . . ?
C8 C9 C10 107.7(2) . . ?
C8 C9 C14 113.4(2) . . ?
C10 C9 C14 114.0(2) . . ?
C11 C10 C9 111.4(3) . . ?
C10 C11 C12 112.1(2) . . ?
C13 C12 C11 110.0(2) . . ?
C17 C12 C11 111.0(2) . . ?
C17 C12 C13 111.4(3) . . ?
C8 C13 C12 112.0(2) . . ?
C15 C14 C9 113.5(3) . . ?
C15 C14 C16 110.6(3) . . ?
C16 C14 C9 110.8(2) . . ?
C22 N21 C25 109.3(3) . . ?
C22 N21 C26 126.1(3) . . ?
C25 N21 C26 124.2(3) . . ?
N21 C22 C38 125.5(3) . . ?
N23 C22 N21 107.2(3) . . ?
N23 C22 C38 127.3(3) . . ?
C22 N23 C24 109.4(3) . . ?
C22 N23 C39 126.5(3) . . ?
C24 N23 C39 124.1(3) . . ?
C25 C24 N23 107.3(3) . . ?
C24 C25 N21 106.8(3) . . ?
O27 C26 N21 110.7(2) . . ?
C26 O27 C28 114.0(2) . . ?
O27 C28 C29 108.3(2) . . ?
O27 C28 C33 111.4(2) . . ?
C33 C28 C29 111.0(2) . . ?
C28 C29 C30 107.6(2) . . ?
C28 C29 C34 113.6(2) . . ?
C30 C29 C34 113.9(2) . . ?
C31 C30 C29 112.0(2) . . ?
C32 C31 C30 111.7(2) . . ?
C31 C32 C33 109.7(2) . . ?
C37 C32 C31 112.0(3) . . ?
C37 C32 C33 111.4(3) . . ?
C28 C33 C32 110.8(2) . . ?
C29 C34 C36 110.6(2) . . ?
C35 C34 C29 113.5(3) . . ?
C35 C34 C36 110.5(3) . . ?

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
O2W H2WA Cl1 0.88(3) 2.29(3) 3.153(3) 166(5) .
O2W H2WB Cl2 0.86(3) 2.32(3) 3.180(3) 172(6) .
O1W H1WA Cl1 0.86(3) 2.34(3) 3.198(3) 175(6) .
O1W H1WB Cl2 0.87(3) 2.28(3) 3.144(3) 174(6) .

_olex2_date_sample_data_collection 2016-09-13
_olex2_date_sample_submission    2016-09-12
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.687
