# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_dna575b_a
_audit_block_doi                 10.5517/ccdc.csd.cc1nzkw2
_database_code_depnum_ccdc_archive 'CCDC 1548725'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.7b02166 2017
_audit_update_record             
;
2017-05-09 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N O'
_chemical_formula_weight         215.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.320(2)
_cell_length_b                   11.047(4)
_cell_length_c                   16.999(6)
_cell_angle_alpha                90.548(9)
_cell_angle_beta                 95.825(9)
_cell_angle_gamma                90.542(9)
_cell_volume                     1180.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3198
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      24.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11115
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.204
_diffrn_reflns_theta_max         24.741
_diffrn_reflns_theta_full        24.741
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3857
_reflns_number_gt                2236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1399P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.107(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3857
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0971
_refine_ls_wR_factor_ref         0.2680
_refine_ls_wR_factor_gt          0.2356
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1A O 0.8841(4) 0.3532(2) 0.25297(15) 0.0574(8) Uani 1 1 d . . . . .
O1B O 0.4435(4) 0.1594(2) 0.25134(15) 0.0563(8) Uani 1 1 d . . . . .
N1A N 0.7863(5) 0.3577(2) 0.37549(17) 0.0470(8) Uani 1 1 d . . . . .
N1B N 0.5385(5) 0.1538(2) 0.12893(17) 0.0478(8) Uani 1 1 d . . . . .
C7B C 0.7876(6) -0.0107(3) 0.1334(2) 0.0432(9) Uani 1 1 d . . . . .
C8A C 0.4843(6) 0.6488(3) 0.3637(2) 0.0469(10) Uani 1 1 d . . . . .
C1A C 0.8765(6) 0.3023(3) 0.3158(2) 0.0452(9) Uani 1 1 d . . . . .
C8B C 0.8298(6) -0.1420(3) 0.13843(19) 0.0449(9) Uani 1 1 d . . . . .
C7A C 0.5289(6) 0.5181(3) 0.3725(2) 0.0443(9) Uani 1 1 d . . . . .
C1B C 0.4500(6) 0.2099(3) 0.1884(2) 0.0437(9) Uani 1 1 d . . . . .
C9B C 0.7022(7) -0.2220(3) 0.1745(2) 0.0540(11) Uani 1 1 d . . . . .
H9B H 0.5840 -0.1933 0.1971 0.065 Uiso 1 1 calc R U . . .
C6B C 0.5947(7) 0.0307(3) 0.1396(2) 0.0488(10) Uani 1 1 d . . . . .
H6B H 0.4901 -0.0239 0.1516 0.059 Uiso 1 1 calc R U . . .
C6A C 0.7197(7) 0.4792(3) 0.3633(2) 0.0484(10) Uani 1 1 d . . . . .
H6A H 0.8184 0.5348 0.3477 0.058 Uiso 1 1 calc R U . . .
C14B C 0.9680(7) 0.0723(3) 0.1233(3) 0.0608(11) Uani 1 1 d . . . . .
H14D H 1.0022 0.0679 0.0696 0.091 Uiso 1 1 calc R U . . .
H14E H 1.0895 0.0492 0.1582 0.091 Uiso 1 1 calc R U . . .
H14F H 0.9294 0.1537 0.1355 0.091 Uiso 1 1 calc R U . . .
C2B C 0.3695(7) 0.3356(3) 0.1761(2) 0.0556(11) Uani 1 1 d . . . . .
H2C H 0.4694 0.3912 0.2050 0.067 Uiso 1 1 calc R U . . .
H2D H 0.2353 0.3421 0.1989 0.067 Uiso 1 1 calc R U . . .
C13A C 0.2924(7) 0.6898(4) 0.3272(2) 0.0627(12) Uani 1 1 d . . . . .
H13A H 0.1872 0.6340 0.3090 0.075 Uiso 1 1 calc R U . . .
C10B C 0.7472(8) -0.3433(3) 0.1777(2) 0.0647(12) Uani 1 1 d . . . . .
H10B H 0.6582 -0.3959 0.2017 0.078 Uiso 1 1 calc R U . . .
C2A C 0.9602(6) 0.1776(3) 0.3292(2) 0.0524(10) Uani 1 1 d . . . . .
H2A H 1.0910 0.1705 0.3042 0.063 Uiso 1 1 calc R U . . .
H2B H 0.8583 0.1204 0.3030 0.063 Uiso 1 1 calc R U . . .
C3A C 1.0041(7) 0.1421(4) 0.4142(2) 0.0624(12) Uani 1 1 d . . . . .
H3A H 1.0236 0.0553 0.4175 0.075 Uiso 1 1 calc R U . . .
H3B H 1.1340 0.1814 0.4372 0.075 Uiso 1 1 calc R U . . .
C13B C 1.0053(7) -0.1889(4) 0.1067(2) 0.0564(11) Uani 1 1 d . . . . .
H13B H 1.0955 -0.1371 0.0826 0.068 Uiso 1 1 calc R U . . .
C5A C 0.7966(8) 0.3122(3) 0.4562(2) 0.0632(12) Uani 1 1 d . . . . .
H5A H 0.6667 0.3329 0.4789 0.076 Uiso 1 1 calc R U . . .
H5B H 0.9144 0.3513 0.4880 0.076 Uiso 1 1 calc R U . . .
C12B C 1.0488(8) -0.3101(4) 0.1101(3) 0.0740(14) Uani 1 1 d . . . . .
H12B H 1.1664 -0.3397 0.0876 0.089 Uiso 1 1 calc R U . . .
C14A C 0.3527(7) 0.4352(3) 0.3880(3) 0.0641(12) Uani 1 1 d . . . . .
H14A H 0.3915 0.3533 0.3773 0.096 Uiso 1 1 calc R U . . .
H14B H 0.2270 0.4556 0.3545 0.096 Uiso 1 1 calc R U . . .
H14C H 0.3255 0.4428 0.4424 0.096 Uiso 1 1 calc R U . . .
C11B C 0.9214(9) -0.3877(4) 0.1460(3) 0.0714(14) Uani 1 1 d . . . . .
H11B H 0.9524 -0.4698 0.1489 0.086 Uiso 1 1 calc R U . . .
C5B C 0.5313(9) 0.2017(4) 0.0491(2) 0.0703(13) Uani 1 1 d . . . . .
H5C H 0.4135 0.1639 0.0165 0.084 Uiso 1 1 calc R U . . .
H5D H 0.6614 0.1805 0.0267 0.084 Uiso 1 1 calc R U . . .
C4A C 0.8250(9) 0.1778(4) 0.4591(3) 0.0743(14) Uani 1 1 d . . . . .
H4A H 0.8533 0.1526 0.5136 0.089 Uiso 1 1 calc R U . . .
H4B H 0.6954 0.1376 0.4365 0.089 Uiso 1 1 calc R U . . .
C9A C 0.6326(7) 0.7360(3) 0.3913(2) 0.0606(12) Uani 1 1 d . . . . .
H9A H 0.7611 0.7119 0.4178 0.073 Uiso 1 1 calc R U . . .
C12A C 0.2543(9) 0.8113(5) 0.3174(3) 0.0775(15) Uani 1 1 d . . . . .
H12A H 0.1248 0.8365 0.2923 0.093 Uiso 1 1 calc R U . . .
C10A C 0.5950(9) 0.8578(4) 0.3805(3) 0.0793(15) Uani 1 1 d . . . . .
H10A H 0.6992 0.9146 0.3980 0.095 Uiso 1 1 calc R U . . .
C11A C 0.4044(10) 0.8949(4) 0.3440(3) 0.0799(16) Uani 1 1 d . . . . .
H11A H 0.3776 0.9770 0.3373 0.096 Uiso 1 1 calc R U . . .
C3B C 0.3366(9) 0.3751(4) 0.0914(3) 0.0816(16) Uani 1 1 d . . . . .
H3C H 0.2019 0.3430 0.0672 0.098 Uiso 1 1 calc R U . . .
H3D H 0.3301 0.4628 0.0897 0.098 Uiso 1 1 calc R U . . .
C4B C 0.5064(10) 0.3341(4) 0.0465(3) 0.0840(16) Uani 1 1 d . . . . .
H4C H 0.6389 0.3727 0.0676 0.101 Uiso 1 1 calc R U . . .
H4D H 0.4764 0.3587 -0.0081 0.101 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.217(4) . ?
O1B C1B 1.215(4) . ?
N1A C1A 1.357(5) . ?
N1A C6A 1.422(4) . ?
N1A C5A 1.461(4) . ?
N1B C1B 1.353(4) . ?
N1B C6B 1.417(4) . ?
N1B C5B 1.458(5) . ?
C7B C6B 1.320(5) . ?
C7B C14B 1.481(5) . ?
C7B C8B 1.479(5) . ?
C8A C9A 1.382(6) . ?
C8A C13A 1.387(6) . ?
C8A C7A 1.480(5) . ?
C1A C2A 1.492(5) . ?
C8B C9B 1.380(5) . ?
C8B C13B 1.385(5) . ?
C7A C6A 1.308(5) . ?
C7A C14A 1.481(5) . ?
C1B C2B 1.492(5) . ?
C9B C10B 1.374(5) . ?
C9B H9B 0.9300 . ?
C6B H6B 0.9300 . ?
C6A H6A 0.9300 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C2B C3B 1.504(6) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C13A C12A 1.375(6) . ?
C13A H13A 0.9300 . ?
C10B C11B 1.367(6) . ?
C10B H10B 0.9300 . ?
C2A C3A 1.501(5) . ?
C2A H2A 0.9700 . ?
C2A H2B 0.9700 . ?
C3A C4A 1.482(6) . ?
C3A H3A 0.9700 . ?
C3A H3B 0.9700 . ?
C13B C12B 1.370(5) . ?
C13B H13B 0.9300 . ?
C5A C4A 1.499(5) . ?
C5A H5A 0.9700 . ?
C5A H5B 0.9700 . ?
C12B C11B 1.361(7) . ?
C12B H12B 0.9300 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C11B H11B 0.9300 . ?
C5B C4B 1.473(5) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C4A H4A 0.9700 . ?
C4A H4B 0.9700 . ?
C9A C10A 1.380(5) . ?
C9A H9A 0.9300 . ?
C12A C11A 1.358(7) . ?
C12A H12A 0.9300 . ?
C10A C11A 1.366(7) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
C3B C4B 1.452(7) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?

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
C1A N1A C6A 117.1(3) . . ?
C1A N1A C5A 124.2(3) . . ?
C6A N1A C5A 117.1(3) . . ?
C1B N1B C6B 117.4(3) . . ?
C1B N1B C5B 123.3(3) . . ?
C6B N1B C5B 117.5(3) . . ?
C6B C7B C14B 121.4(3) . . ?
C6B C7B C8B 120.4(4) . . ?
C14B C7B C8B 118.2(3) . . ?
C9A C8A C13A 116.8(4) . . ?
C9A C8A C7A 121.5(4) . . ?
C13A C8A C7A 121.7(4) . . ?
O1A C1A N1A 120.2(3) . . ?
O1A C1A C2A 121.7(3) . . ?
N1A C1A C2A 118.1(3) . . ?
C9B C8B C13B 117.3(3) . . ?
C9B C8B C7B 123.0(3) . . ?
C13B C8B C7B 119.7(4) . . ?
C6A C7A C14A 122.3(3) . . ?
C6A C7A C8A 119.0(4) . . ?
C14A C7A C8A 118.6(3) . . ?
O1B C1B N1B 119.9(3) . . ?
O1B C1B C2B 121.2(3) . . ?
N1B C1B C2B 118.8(3) . . ?
C10B C9B C8B 121.0(4) . . ?
C10B C9B H9B 119.5 . . ?
C8B C9B H9B 119.5 . . ?
C7B C6B N1B 123.5(4) . . ?
C7B C6B H6B 118.2 . . ?
N1B C6B H6B 118.2 . . ?
C7A C6A N1A 124.3(4) . . ?
C7A C6A H6A 117.8 . . ?
N1A C6A H6A 117.8 . . ?
C7B C14B H14D 109.5 . . ?
C7B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C7B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C1B C2B C3B 115.3(3) . . ?
C1B C2B H2C 108.4 . . ?
C3B C2B H2C 108.4 . . ?
C1B C2B H2D 108.4 . . ?
C3B C2B H2D 108.4 . . ?
H2C C2B H2D 107.5 . . ?
C12A C13A C8A 121.4(5) . . ?
C12A C13A H13A 119.3 . . ?
C8A C13A H13A 119.3 . . ?
C11B C10B C9B 120.7(4) . . ?
C11B C10B H10B 119.6 . . ?
C9B C10B H10B 119.6 . . ?
C1A C2A C3A 115.3(3) . . ?
C1A C2A H2A 108.5 . . ?
C3A C2A H2A 108.5 . . ?
C1A C2A H2B 108.5 . . ?
C3A C2A H2B 108.5 . . ?
H2A C2A H2B 107.5 . . ?
C4A C3A C2A 110.3(4) . . ?
C4A C3A H3A 109.6 . . ?
C2A C3A H3A 109.6 . . ?
C4A C3A H3B 109.6 . . ?
C2A C3A H3B 109.6 . . ?
H3A C3A H3B 108.1 . . ?
C12B C13B C8B 121.3(4) . . ?
C12B C13B H13B 119.4 . . ?
C8B C13B H13B 119.4 . . ?
N1A C5A C4A 112.0(3) . . ?
N1A C5A H5A 109.2 . . ?
C4A C5A H5A 109.2 . . ?
N1A C5A H5B 109.2 . . ?
C4A C5A H5B 109.2 . . ?
H5A C5A H5B 107.9 . . ?
C11B C12B C13B 120.6(4) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B H12B 119.7 . . ?
C7A C14A H14A 109.5 . . ?
C7A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C7A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C12B C11B C10B 119.1(4) . . ?
C12B C11B H11B 120.5 . . ?
C10B C11B H11B 120.5 . . ?
N1B C5B C4B 113.1(3) . . ?
N1B C5B H5C 109.0 . . ?
C4B C5B H5C 109.0 . . ?
N1B C5B H5D 109.0 . . ?
C4B C5B H5D 109.0 . . ?
H5C C5B H5D 107.8 . . ?
C3A C4A C5A 110.2(4) . . ?
C3A C4A H4A 109.6 . . ?
C5A C4A H4A 109.6 . . ?
C3A C4A H4B 109.6 . . ?
C5A C4A H4B 109.6 . . ?
H4A C4A H4B 108.1 . . ?
C10A C9A C8A 121.7(4) . . ?
C10A C9A H9A 119.2 . . ?
C8A C9A H9A 119.2 . . ?
C11A C12A C13A 120.5(5) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A H12A 119.7 . . ?
C11A C10A C9A 119.9(5) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C12A C11A C10A 119.7(4) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C4B C3B C2B 111.8(4) . . ?
C4B C3B H3C 109.3 . . ?
C2B C3B H3C 109.3 . . ?
C4B C3B H3D 109.3 . . ?
C2B C3B H3D 109.3 . . ?
H3C C3B H3D 107.9 . . ?
C3B C4B C5B 112.3(4) . . ?
C3B C4B H4C 109.2 . . ?
C5B C4B H4C 109.2 . . ?
C3B C4B H4D 109.2 . . ?
C5B C4B H4D 109.2 . . ?
H4C C4B H4D 107.9 . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1817608'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H26 Cl2 N2 Ni O7'
_chemical_formula_weight         439.96

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9966(10)
_cell_length_b                   12.0579(17)
_cell_length_c                   12.9998(18)
_cell_angle_alpha                63.724(3)
_cell_angle_beta                 88.610(3)
_cell_angle_gamma                86.344(3)
_cell_volume                     981.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9822
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      31.91

_exptl_crystal_description       platelet
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18734
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         31.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6699
_reflns_number_gt                5369
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1109P)²+0.2902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6699
_refine_ls_number_parameters     261
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Ni Ni 0.68047(4) 0.65613(2) 0.68197(2) 0.02457(11) Uani 1 1 d . . . . .
Cl1 Cl 0.35969(9) 0.58889(6) 0.68538(6) 0.03514(15) Uani 1 1 d . . . . .
O1 O 0.7871(3) 0.58232(19) 0.57655(17) 0.0396(4) Uani 1 1 d D . . . .
O2 O 0.6012(3) 0.81428(18) 0.53874(17) 0.0396(4) Uani 1 1 d D . . . .
O3 O 0.9490(3) 0.7296(2) 0.6636(2) 0.0456(5) Uani 1 1 d D . . . .
N1 N 0.7607(3) 0.50223(18) 0.82872(17) 0.0273(4) Uani 1 1 d . . . . .
O4W O 0.6745(4) 0.3654(2) 0.5772(2) 0.0493(5) Uani 1 1 d . . . . .
N2 N 0.6213(3) 0.72079(19) 0.80169(17) 0.0280(4) Uani 1 1 d . . . . .
O5W O 0.3666(4) 0.3092(2) 0.7253(3) 0.0587(6) Uani 1 1 d D . . . .
C6 C 0.6703(3) 0.6398(2) 0.9099(2) 0.0271(4) Uani 1 1 d . . . . .
O3W O 0.2624(4) 0.9551(3) 0.5055(3) 0.0643(7) Uani 1 1 d D . . . .
C5 C 0.7435(3) 0.5162(2) 0.92505(19) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.8736(4) 0.2905(2) 0.9376(2) 0.0363(5) Uani 1 1 d . . . . .
C1 C 0.8238(4) 0.3917(2) 0.8355(2) 0.0335(5) Uani 1 1 d . . . . .
H1 H 0.834523 0.382831 0.768014 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7925(4) 0.4202(3) 1.0304(2) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.782051 0.431508 1.096653 0.042 Uiso 1 1 calc R U . . .
C7 C 0.6528(4) 0.6729(3) 0.9987(2) 0.0370(5) Uani 1 1 d . . . . .
H7 H 0.684612 0.615856 1.073429 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5573(4) 0.8354(2) 0.7806(2) 0.0345(5) Uani 1 1 d . . . . .
H10 H 0.522954 0.890296 0.705641 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5390(4) 0.8774(3) 0.8644(3) 0.0390(6) Uani 1 1 d . . . . .
C3 C 0.8577(4) 0.3064(3) 1.0363(2) 0.0393(6) Uani 1 1 d . . . . .
H3 H 0.890612 0.240759 1.106794 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5865(4) 0.7934(3) 0.9744(3) 0.0424(6) Uani 1 1 d . . . . .
H8 H 0.574426 0.817096 1.033350 0.051 Uiso 1 1 calc R U . . .
C11 C 0.9391(6) 0.1682(3) 0.9399(3) 0.0539(8) Uani 1 1 d . . . . .
H11A H 0.985421 0.112518 1.015294 0.081 Uiso 1 1 calc R U . . .
H11C H 1.039948 0.180474 0.885233 0.081 Uiso 1 1 calc R U . . .
H11B H 0.833554 0.133670 0.920693 0.081 Uiso 1 1 calc R U . . .
C12 C 0.4729(7) 1.0088(3) 0.8323(4) 0.0632(10) Uani 1 1 d . . . . .
H12B H 0.420525 1.015260 0.898515 0.095 Uiso 1 1 calc R U . . .
H12A H 0.376291 1.035099 0.773684 0.095 Uiso 1 1 calc R U . . .
H12C H 0.579315 1.060520 0.804063 0.095 Uiso 1 1 calc R U . . .
Cl2 Cl 1.01600(16) 0.96792(8) 0.70074(9) 0.0625(3) Uani 1 1 d . . . . .
O6W O 0.0467(4) 0.2567(2) 0.6272(2) 0.0498(5) Uani 1 1 d . . . . .
H3W H 0.969(6) 0.789(3) 0.681(3) 0.060 Uiso 1 1 d D U . . .
H33W H 1.058(4) 0.691(4) 0.664(4) 0.060 Uiso 1 1 d D U . . .
H1W H 0.724(5) 0.533(3) 0.563(4) 0.060 Uiso 1 1 d D U . . .
H22W H 0.669(5) 0.879(3) 0.517(4) 0.060 Uiso 1 1 d D U . . .
H5W H 0.288(5) 0.303(4) 0.679(3) 0.060 Uiso 1 1 d D U . . .
H55W H 0.337(6) 0.3889(19) 0.702(4) 0.060 Uiso 1 1 d D U . . .
H2W H 0.481(3) 0.839(4) 0.535(4) 0.060 Uiso 1 1 d D U . . .
H11W H 0.836(6) 0.632(4) 0.514(4) 0.060 Uiso 1 1 d . U . . .
H4W H 0.644(6) 0.374(4) 0.508(4) 0.060 Uiso 1 1 d . U . . .
H44W H 0.594(6) 0.346(5) 0.610(4) 0.060 Uiso 1 1 d . U . . .
H32W H 0.245(6) 0.906(3) 0.470(3) 0.060 Uiso 1 1 d D U . . .
H31W H 0.185(5) 0.934(4) 0.567(3) 0.060 Uiso 1 1 d D U . . .
H61W H -0.048(6) 0.286(4) 0.604(4) 0.060 Uiso 1 1 d . U . . .
H62W H 0.042(6) 0.181(5) 0.636(4) 0.060 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni O1 2.0426(19) . ?
Ni O2 2.0451(19) . ?
Ni N1 2.045(2) . ?
Ni N2 2.050(2) . ?
Ni O3 2.092(2) . ?
Ni Cl1 2.4274(7) . ?
O1 H1W 0.849(19) . ?
O1 H11W 0.85(4) . ?
O2 H22W 0.874(19) . ?
O2 H2W 0.872(19) . ?
O3 H3W 0.866(18) . ?
O3 H33W 0.868(19) . ?
N1 C5 1.337(3) . ?
N1 C1 1.342(3) . ?
O4W H4W 0.89(5) . ?
O4W H44W 0.68(4) . ?
N2 C10 1.333(3) . ?
N2 C6 1.347(3) . ?
O5W H5W 0.860(19) . ?
O5W H55W 0.883(19) . ?
C6 C7 1.380(3) . ?
C6 C5 1.473(3) . ?
O3W H32W 0.913(19) . ?
O3W H31W 0.906(19) . ?
C5 C4 1.379(3) . ?
C2 C3 1.379(4) . ?
C2 C1 1.381(4) . ?
C2 C11 1.503(4) . ?
C1 H1 0.9300 . ?
C4 C3 1.387(4) . ?
C4 H4 0.9300 . ?
C7 C8 1.393(4) . ?
C7 H7 0.9300 . ?
C10 C9 1.391(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.370(4) . ?
C9 C12 1.493(4) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11C 0.9600 . ?
C11 H11B 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?
O6W H61W 0.73(4) . ?
O6W H62W 0.87(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni O2 88.30(9) . . ?
O1 Ni N1 93.76(8) . . ?
O2 Ni N1 177.68(8) . . ?
O1 Ni N2 169.63(9) . . ?
O2 Ni N2 98.09(8) . . ?
N1 Ni N2 79.72(8) . . ?
O1 Ni O3 85.11(9) . . ?
O2 Ni O3 86.31(9) . . ?
N1 Ni O3 92.78(9) . . ?
N2 Ni O3 87.14(9) . . ?
O1 Ni Cl1 94.34(7) . . ?
O2 Ni Cl1 87.93(6) . . ?
N1 Ni Cl1 92.99(6) . . ?
N2 Ni Cl1 94.06(6) . . ?
O3 Ni Cl1 174.23(7) . . ?
Ni O1 H1W 121(3) . . ?
Ni O1 H11W 117(3) . . ?
H1W O1 H11W 107(4) . . ?
Ni O2 H22W 120(3) . . ?
Ni O2 H2W 116(3) . . ?
H22W O2 H2W 108(4) . . ?
Ni O3 H3W 122(3) . . ?
Ni O3 H33W 126(3) . . ?
H3W O3 H33W 108(4) . . ?
C5 N1 C1 119.1(2) . . ?
C5 N1 Ni 114.97(16) . . ?
C1 N1 Ni 125.97(17) . . ?
H4W O4W H44W 106(5) . . ?
C10 N2 C6 119.0(2) . . ?
C10 N2 Ni 126.36(18) . . ?
C6 N2 Ni 114.35(15) . . ?
H5W O5W H55W 93(4) . . ?
N2 C6 C7 121.2(2) . . ?
N2 C6 C5 115.4(2) . . ?
C7 C6 C5 123.4(2) . . ?
H32W O3W H31W 111(4) . . ?
N1 C5 C4 121.3(2) . . ?
N1 C5 C6 115.4(2) . . ?
C4 C5 C6 123.3(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 C11 122.0(3) . . ?
C1 C2 C11 120.8(3) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
N2 C10 C9 123.6(3) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 C12 123.2(3) . . ?
C10 C9 C12 120.0(3) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H61W O6W H62W 104(4) . . ?

_refine_diff_density_max         1.554
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.126

