# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_M14H
_database_code_depnum_ccdc_archive 'CCDC 1912603'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-04-27 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H31 Br N2'
_chemical_formula_weight         331.34

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_vrf_PLAT029_M14H                
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.902 Why?  
RESPONSE: The data completeness is limited by the setup of the STOE IPDS I
and in part poor crystallinity 
;
_vrf_PLAT911_M14H                
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.597        316 Report
RESPONSE: Due to STOE IPDS I setup and in part poor crystallinity 
;


_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                   6.9890(14)
_cell_length_b                   8.3080(17)
_cell_length_c                   16.476(3)
_cell_angle_alpha                83.84(3)
_cell_angle_beta                 78.78(3)
_cell_angle_gamma                79.10(3)
_cell_volume                     919.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7592
_cell_measurement_theta_min      2.886
_cell_measurement_theta_max      25.098

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   'X-Red, X-Shape'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS I'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7592
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.886
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_full        25.098
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.902
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.902
_reflns_number_total             2953
_reflns_number_gt                2052
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1047P)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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.078(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
C1 C -0.6827(11) 1.4558(7) 0.1223(5) 0.0482(16) Uani 1 1 d . . . . .
H1 H -0.803656 1.523886 0.137474 0.058 Uiso 1 1 calc R U . . .
C2 C -0.4486(10) 1.2739(6) 0.0538(4) 0.0388(14) Uani 1 1 d . . . . .
C3 C -0.5237(11) 1.4385(7) 0.1594(5) 0.0478(16) Uani 1 1 d . . . . .
H3 H -0.513406 1.491972 0.204731 0.057 Uiso 1 1 calc R U . . .
N3 N -0.6337(8) 1.3541(6) 0.0575(4) 0.0422(13) Uani 1 1 d . . . . .
H3A H -0.711363 1.344007 0.024477 0.051 Uiso 1 1 calc R U . . .
C4 C -0.3423(10) 1.1554(7) -0.0069(5) 0.0458(16) Uani 1 1 d . . . . .
H4A H -0.423422 1.150341 -0.047049 0.069 Uiso 1 1 calc R U . . .
H4B H -0.313283 1.048784 0.021230 0.069 Uiso 1 1 calc R U . . .
H4C H -0.220990 1.189919 -0.034458 0.069 Uiso 1 1 calc R U . . .
C5 C -0.1763(10) 1.2730(7) 0.1332(5) 0.0470(16) Uani 1 1 d . . . . .
H5A H -0.133722 1.365985 0.151068 0.056 Uiso 1 1 calc R U . . .
H5AB H -0.088289 1.241137 0.082187 0.056 Uiso 1 1 calc R U . . .
C6 C -0.1560(10) 1.1302(7) 0.1993(5) 0.0446(15) Uani 1 1 d . . . . .
H6A H -0.235449 1.163139 0.251939 0.054 Uiso 1 1 calc R U . . .
H6AB H -0.203508 1.037794 0.183543 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0598(11) 1.0799(7) 0.2083(4) 0.0452(16) Uani 1 1 d . . . . .
H7A H 0.102495 1.172706 0.226284 0.054 Uiso 1 1 calc R U . . .
H7AB H 0.137812 1.056914 0.154044 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1063(10) 0.9317(7) 0.2683(5) 0.0466(16) Uani 1 1 d . . . . .
H8A H 0.034101 0.955177 0.323432 0.056 Uiso 1 1 calc R U . . .
H8AB H 0.061666 0.838531 0.251711 0.056 Uiso 1 1 calc R U . . .
C9 C 0.3263(10) 0.8867(7) 0.2710(4) 0.0453(15) Uani 1 1 d . . . . .
H9A H 0.370147 0.981083 0.286768 0.054 Uiso 1 1 calc R U . . .
H9AB H 0.397354 0.863594 0.215674 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3821(10) 0.7394(7) 0.3307(4) 0.0453(15) Uani 1 1 d . . . . .
H10A H 0.318821 0.764362 0.386822 0.054 Uiso 1 1 calc R U . . .
H10B H 0.332991 0.645731 0.317166 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6037(10) 0.6949(7) 0.3268(4) 0.0446(15) Uani 1 1 d . . . . .
H11A H 0.649344 0.784744 0.346185 0.053 Uiso 1 1 calc R U . . .
H11B H 0.666972 0.683621 0.269393 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6707(11) 0.5363(8) 0.3781(5) 0.0502(17) Uani 1 1 d . . . . .
H12A H 0.614234 0.549420 0.436097 0.060 Uiso 1 1 calc R U . . .
H12B H 0.619657 0.447042 0.360896 0.060 Uiso 1 1 calc R U . . .
C13 C 0.8950(11) 0.4902(8) 0.3690(5) 0.0485(16) Uani 1 1 d . . . . .
H13A H 0.945757 0.580216 0.385555 0.058 Uiso 1 1 calc R U . . .
H13B H 0.950935 0.476351 0.311015 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9647(11) 0.3332(7) 0.4203(5) 0.0500(17) Uani 1 1 d . . . . .
H14A H 0.906739 0.345899 0.478247 0.060 Uiso 1 1 calc R U . . .
H14B H 0.916913 0.242451 0.402930 0.060 Uiso 1 1 calc R U . . .
C15 C 1.1874(12) 0.2912(8) 0.4122(5) 0.059(2) Uani 1 1 d . . . . .
H15A H 1.235139 0.383626 0.427893 0.071 Uiso 1 1 calc R U . . .
H15B H 1.244663 0.275695 0.354457 0.071 Uiso 1 1 calc R U . . .
C16 C 1.2596(16) 0.1388(10) 0.4644(6) 0.074(3) Uani 1 1 d . . . . .
H16A H 1.232587 0.043714 0.443357 0.112 Uiso 1 1 calc R U . . .
H16B H 1.192459 0.147462 0.520861 0.112 Uiso 1 1 calc R U . . .
H16C H 1.399647 0.128675 0.462198 0.112 Uiso 1 1 calc R U . . .
N2 N -0.3778(8) 1.3248(6) 0.1162(4) 0.0416(13) Uani 1 1 d . . . . .
Br01 Br 0.84530(10) 0.72017(7) 0.08930(4) 0.0438(3) 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
C1 C3 1.347(10) . ?
C1 N3 1.383(10) . ?
C2 N3 1.331(8) . ?
C2 N2 1.360(9) . ?
C2 C4 1.472(10) . ?
C3 N2 1.391(9) . ?
C5 N2 1.465(9) . ?
C5 C6 1.527(8) . ?
C6 C7 1.519(10) . ?
C7 C8 1.520(8) . ?
C8 C9 1.520(10) . ?
C9 C10 1.525(8) . ?
C10 C11 1.513(10) . ?
C11 C12 1.533(8) . ?
C12 C13 1.523(10) . ?
C13 C14 1.529(9) . ?
C14 C15 1.511(11) . ?
C15 C16 1.514(10) . ?

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
C3 C1 N3 107.7(6) . . ?
N3 C2 N2 106.5(6) . . ?
N3 C2 C4 126.3(6) . . ?
N2 C2 C4 127.2(6) . . ?
C1 C3 N2 106.2(6) . . ?
C2 N3 C1 110.0(6) . . ?
N2 C5 C6 114.0(5) . . ?
C7 C6 C5 109.6(5) . . ?
C6 C7 C8 115.9(5) . . ?
C9 C8 C7 112.3(5) . . ?
C8 C9 C10 114.7(5) . . ?
C11 C10 C9 112.1(5) . . ?
C10 C11 C12 114.6(5) . . ?
C13 C12 C11 113.1(5) . . ?
C12 C13 C14 113.9(6) . . ?
C15 C14 C13 113.3(6) . . ?
C14 C15 C16 114.2(7) . . ?
C2 N2 C3 109.6(6) . . ?
C2 N2 C5 125.3(6) . . ?
C3 N2 C5 125.1(6) . . ?

_refine_diff_density_max         0.837
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_cu_OliC12C12new_0m
_database_code_depnum_ccdc_archive 'CCDC 1912605'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-04-27 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H57 Br N2 O'
_chemical_formula_weight         517.66

_vrf_THETM01_cu_OliC12C12new_0m  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Due to poor crystallinity. Data collected up to 2theta = 90.
;

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'
Br Br -0.6763 1.2805 '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      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                   7.595(7)
_cell_length_b                   9.979(10)
_cell_length_c                   20.822(19)
_cell_angle_alpha                85.10(3)
_cell_angle_beta                 83.70(4)
_cell_angle_gamma                84.22(3)
_cell_volume                     1556(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7672
_cell_measurement_theta_min      2.141
_cell_measurement_theta_max      44.652

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.928
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7672
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         44.652
_diffrn_reflns_theta_full        44.652
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2425
_reflns_number_gt                1984
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0231P)²+4.4641P] 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         2425
_refine_ls_number_parameters     291
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.167
_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
Br01 Br 1.04447(13) 0.78680(9) -0.07319(5) 0.0817(4) Uani 1 1 d . . . . .
N002 N 0.4048(12) 0.6842(7) 0.0746(3) 0.0554(18) Uani 1 1 d . . . . .
N003 N 0.4509(13) 0.4660(7) 0.0849(3) 0.0525(18) Uani 1 1 d . . . . .
C4 C 0.6130(13) 0.5168(11) 0.0785(3) 0.057(2) Uani 1 1 d . . . . .
H4 H 0.723081 0.466553 0.078122 0.068 Uiso 1 1 calc R U . . .
O1W O 0.8131(11) 0.9075(7) 0.0582(4) 0.154(3) Uani 1 1 d D . . . .
H1 H 0.879(13) 0.886(11) 0.021(3) 0.185 Uiso 1 1 d D U . . .
H2 H 0.850(13) 0.977(8) 0.076(5) 0.185 Uiso 1 1 d D U . . .
C005 C 0.4228(10) 0.3215(7) 0.0988(4) 0.061(2) Uani 1 1 d . . . . .
H00A H 0.305757 0.306624 0.087805 0.073 Uiso 1 1 calc R U . . .
H00B H 0.510313 0.267959 0.071818 0.073 Uiso 1 1 calc R U . . .
C007 C 0.3257(14) 0.5691(13) 0.0827(3) 0.058(2) Uani 1 1 d . . . . .
C008 C 0.5858(15) 0.6488(11) 0.0730(3) 0.058(2) Uani 1 1 d . . . . .
H008 H 0.673499 0.708530 0.068707 0.070 Uiso 1 1 calc R U . . .
C009 C 0.3240(11) 0.8259(8) 0.0737(4) 0.071(2) Uani 1 1 d . . . . .
H00C H 0.197737 0.827830 0.069648 0.085 Uiso 1 1 calc R U . . .
H00D H 0.377574 0.877601 0.036347 0.085 Uiso 1 1 calc R U . . .
C00A C 0.2122(11) 0.8354(8) 0.4440(4) 0.074(2) Uani 1 1 d . . . . .
H00E H 0.083937 0.837983 0.444690 0.089 Uiso 1 1 calc R U . . .
H00F H 0.258491 0.741416 0.449820 0.089 Uiso 1 1 calc R U . . .
C00B C 0.2765(11) 0.8189(8) 0.1973(4) 0.068(2) Uani 1 1 d . . . . .
H00G H 0.329417 0.726195 0.200222 0.082 Uiso 1 1 calc R U . . .
H00H H 0.149147 0.816833 0.197211 0.082 Uiso 1 1 calc R U . . .
C00C C 0.1334(12) 0.5643(8) 0.0857(4) 0.078(3) Uani 1 1 d . . . . .
H00I H 0.088357 0.620889 0.050355 0.118 Uiso 1 1 calc R U . . .
H00J H 0.078044 0.595868 0.125978 0.118 Uiso 1 1 calc R U . . .
H00K H 0.107412 0.473046 0.082599 0.118 Uiso 1 1 calc R U . . .
C00D C 0.1784(11) 0.8565(8) 0.5659(4) 0.076(3) Uani 1 1 d . . . . .
H00L H 0.222851 0.762430 0.572989 0.091 Uiso 1 1 calc R U . . .
H00M H 0.050238 0.859842 0.565992 0.091 Uiso 1 1 calc R U . . .
C00E C 0.2458(11) 0.8217(8) 0.3211(4) 0.073(2) Uani 1 1 d . . . . .
H00N H 0.298542 0.729092 0.324894 0.088 Uiso 1 1 calc R U . . .
H00O H 0.117931 0.819468 0.322865 0.088 Uiso 1 1 calc R U . . .
C00F C 0.3671(12) 0.2973(8) 0.2863(4) 0.078(3) Uani 1 1 d . . . . .
H00P H 0.328541 0.206954 0.292140 0.094 Uiso 1 1 calc R U . . .
H00Q H 0.494138 0.287379 0.289807 0.094 Uiso 1 1 calc R U . . .
C00G C 0.3218(11) 0.3221(9) 0.4068(4) 0.081(3) Uani 1 1 d . . . . .
H00R H 0.449872 0.317617 0.407014 0.097 Uiso 1 1 calc R U . . .
H00S H 0.290385 0.229768 0.413882 0.097 Uiso 1 1 calc R U . . .
C00H C 0.3500(11) 0.8896(8) 0.1341(4) 0.073(3) Uani 1 1 d . . . . .
H00T H 0.294638 0.981593 0.131275 0.088 Uiso 1 1 calc R U . . .
H00U H 0.476466 0.894259 0.135377 0.088 Uiso 1 1 calc R U . . .
C00I C 0.2877(11) 0.8938(8) 0.3784(4) 0.076(3) Uani 1 1 d . . . . .
H00V H 0.415847 0.891086 0.377873 0.091 Uiso 1 1 calc R U . . .
H00W H 0.241692 0.987900 0.372850 0.091 Uiso 1 1 calc R U . . .
C00J C 0.2551(11) 0.9089(8) 0.5000(4) 0.071(2) Uani 1 1 d . . . . .
H00X H 0.383432 0.904197 0.499587 0.086 Uiso 1 1 calc R U . . .
H00Y H 0.212151 1.003401 0.493092 0.086 Uiso 1 1 calc R U . . .
C00K C 0.3123(11) 0.8867(8) 0.2565(4) 0.075(3) Uani 1 1 d . . . . .
H00Z H 0.439724 0.890200 0.255479 0.090 Uiso 1 1 calc R U . . .
H010 H 0.258653 0.979151 0.253069 0.090 Uiso 1 1 calc R U . . .
C00L C 0.2186(10) 0.9313(8) 0.6222(4) 0.070(2) Uani 1 1 d . . . . .
H011 H 0.346750 0.927534 0.622124 0.084 Uiso 1 1 calc R U . . .
H012 H 0.174839 1.025488 0.614845 0.084 Uiso 1 1 calc R U . . .
C00M C 0.1416(12) 0.8802(9) 0.6883(4) 0.087(3) Uani 1 1 d . . . . .
H013 H 0.185433 0.786103 0.695952 0.105 Uiso 1 1 calc R U . . .
H014 H 0.013311 0.884160 0.688661 0.105 Uiso 1 1 calc R U . . .
C00N C 0.2869(12) 0.3458(9) 0.5284(5) 0.088(3) Uani 1 1 d . . . . .
H015 H 0.415101 0.344202 0.527465 0.105 Uiso 1 1 calc R U . . .
H016 H 0.259671 0.252451 0.535544 0.105 Uiso 1 1 calc R U . . .
C00O C 0.3457(13) 0.3447(9) 0.2193(4) 0.091(3) Uani 1 1 d . . . . .
H017 H 0.219827 0.348087 0.214194 0.110 Uiso 1 1 calc R U . . .
HA17 H 0.377109 0.437128 0.213468 0.110 Uiso 1 1 calc R U . . .
C00P C 0.4373(15) 0.2765(8) 0.1676(4) 0.106(4) Uani 1 1 d . . . . .
H018 H 0.404049 0.184572 0.173429 0.127 Uiso 1 1 calc R U . . .
H019 H 0.562720 0.271455 0.173634 0.127 Uiso 1 1 calc R U . . .
C00Q C 0.2558(14) 0.3693(10) 0.6489(5) 0.104(3) Uani 1 1 d . . . . .
H01A H 0.384266 0.366622 0.647176 0.125 Uiso 1 1 calc R U . . .
H11A H 0.226844 0.276557 0.657216 0.125 Uiso 1 1 calc R U . . .
C00R C 0.2464(16) 0.3889(9) 0.4640(5) 0.126(4) Uani 1 1 d . . . . .
H01B H 0.274525 0.481973 0.456460 0.151 Uiso 1 1 calc R U . . .
H01C H 0.118294 0.390722 0.464680 0.151 Uiso 1 1 calc R U . . .
C00S C 0.2863(15) 0.3660(9) 0.3421(5) 0.114(4) Uani 1 1 d . . . . .
H01D H 0.315910 0.458812 0.334799 0.137 Uiso 1 1 calc R U . . .
H01E H 0.158617 0.368537 0.341186 0.137 Uiso 1 1 calc R U . . .
C00T C 0.1845(14) 0.9575(11) 0.7435(5) 0.131(3) Uani 1 1 d . . . . .
H01F H 0.311258 0.955927 0.743063 0.196 Uiso 1 1 calc R U . . .
H01G H 0.135876 0.916051 0.783963 0.196 Uiso 1 1 calc R U . . .
H01H H 0.133683 1.049291 0.738238 0.196 Uiso 1 1 calc R U . . .
C00U C 0.2137(17) 0.4096(10) 0.5864(5) 0.132(4) Uani 1 1 d . . . . .
H01I H 0.238346 0.503485 0.578839 0.159 Uiso 1 1 calc R U . . .
H11I H 0.085642 0.409171 0.587914 0.159 Uiso 1 1 calc R U . . .
C00V C 0.1862(18) 0.4363(12) 0.7057(5) 0.153(5) Uani 1 1 d . . . . .
H01J H 0.206211 0.530668 0.695818 0.183 Uiso 1 1 calc R U . . .
H11J H 0.058364 0.432306 0.709247 0.183 Uiso 1 1 calc R U . . .
C00W C 0.2362(14) 0.4027(11) 0.7672(5) 0.131(3) Uani 1 1 d . . . . .
H01K H 0.170333 0.462623 0.796800 0.157 Uiso 1 1 calc R U . . .
H01L H 0.211780 0.311405 0.780623 0.157 Uiso 1 1 calc R U . . .
H01M H 0.361123 0.410762 0.767057 0.157 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
N002 C007 1.338(9) . ?
N002 C008 1.382(9) . ?
N002 C009 1.484(9) . ?
N003 C007 1.330(9) . ?
N003 C4 1.367(9) . ?
N003 C005 1.478(9) . ?
C4 C008 1.309(9) . ?
C005 C00P 1.477(10) . ?
C007 C00C 1.461(10) . ?
C009 C00H 1.496(9) . ?
C00A C00J 1.511(10) . ?
C00A C00I 1.515(10) . ?
C00B C00H 1.518(10) . ?
C00B C00K 1.517(9) . ?
C00D C00J 1.503(10) . ?
C00D C00L 1.516(10) . ?
C00E C00K 1.501(10) . ?
C00E C00I 1.523(10) . ?
C00F C00S 1.446(11) . ?
C00F C00O 1.456(10) . ?
C00G C00S 1.425(11) . ?
C00G C00R 1.450(11) . ?
C00L C00M 1.503(10) . ?
C00M C00T 1.519(11) . ?
C00N C00R 1.429(11) . ?
C00N C00U 1.445(11) . ?
C00O C00P 1.405(10) . ?
C00Q C00U 1.389(11) . ?
C00Q C00V 1.432(12) . ?
C00V C00W 1.381(12) . ?

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
C007 N002 C008 106.9(7) . . ?
C007 N002 C009 129.4(10) . . ?
C008 N002 C009 123.4(9) . . ?
C007 N003 C4 108.3(7) . . ?
C007 N003 C005 126.7(9) . . ?
C4 N003 C005 124.7(9) . . ?
C008 C4 N003 107.8(8) . . ?
C00P C005 N003 111.9(6) . . ?
N003 C007 N002 108.5(8) . . ?
N003 C007 C00C 128.0(10) . . ?
N002 C007 C00C 123.4(11) . . ?
C4 C008 N002 108.4(8) . . ?
N002 C009 C00H 111.4(6) . . ?
C00J C00A C00I 113.7(7) . . ?
C00H C00B C00K 113.0(7) . . ?
C00J C00D C00L 115.6(7) . . ?
C00K C00E C00I 113.7(7) . . ?
C00S C00F C00O 124.7(8) . . ?
C00S C00G C00R 125.0(8) . . ?
C009 C00H C00B 116.0(7) . . ?
C00A C00I C00E 114.7(7) . . ?
C00D C00J C00A 115.4(7) . . ?
C00E C00K C00B 116.3(7) . . ?
C00M C00L C00D 116.1(7) . . ?
C00L C00M C00T 114.6(8) . . ?
C00R C00N C00U 125.7(9) . . ?
C00P C00O C00F 121.3(8) . . ?
C00O C00P C005 123.5(8) . . ?
C00U C00Q C00V 125.0(10) . . ?
C00N C00R C00G 124.4(9) . . ?
C00G C00S C00F 123.0(8) . . ?
C00Q C00U C00N 125.7(10) . . ?
C00W C00V C00Q 125.5(11) . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_mo_vsOliM3Hb_0ma
_database_code_depnum_ccdc_archive 'CCDC 1912604'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Smetana'
;Stockholm University
Sweden
;
_audit_update_record             
;
2019-04-27 deposited with the CCDC.	2021-01-08 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            'C17 H33 Br N2'
_chemical_formula_weight         345.36

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.4530(13)
_cell_length_b                   8.5697(5)
_cell_length_c                   10.2184(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.870(2)
_cell_angle_gamma                90
_cell_volume                     1965.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    24952
_cell_measurement_theta_min      2.544
_cell_measurement_theta_max      28.319

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    2.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24952
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4880
_reflns_number_gt                2756
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0537P)²+1.3379P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4880
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_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
Br01 Br 0.88272(2) 0.44297(4) 1.24873(4) 0.06090(16) Uani 1 1 d . . . . .
N1 N 0.86887(11) 0.5310(3) 0.9022(3) 0.0489(7) Uani 1 1 d . . . . .
N2 N 0.94524(11) 0.6780(3) 0.9273(3) 0.0471(7) Uani 1 1 d . . . . .
C1 C 0.28916(18) 0.0864(6) 0.2022(5) 0.0866(15) Uani 1 1 d . . . . .
H14 H 0.290443 0.179947 0.150696 0.130 Uiso 1 1 calc R U . . .
H15 H 0.248428 0.059052 0.216552 0.130 Uiso 1 1 calc R U . . .
H1 H 0.308178 0.003097 0.156682 0.130 Uiso 1 1 calc R U . . .
C2 C 0.32127(16) 0.1133(6) 0.3322(4) 0.0689(11) Uani 1 1 d . . . . .
H12 H 0.319228 0.018768 0.384079 0.083 Uiso 1 1 calc R U . . .
H13 H 0.300911 0.195109 0.378833 0.083 Uiso 1 1 calc R U . . .
C3 C 0.38577(14) 0.1587(5) 0.3200(3) 0.0611(10) Uani 1 1 d . . . . .
H16 H 0.387615 0.251706 0.266147 0.073 Uiso 1 1 calc R U . . .
H17 H 0.406062 0.075829 0.274669 0.073 Uiso 1 1 calc R U . . .
C4 C 0.41898(15) 0.1899(5) 0.4482(4) 0.0654(11) Uani 1 1 d . . . . .
H18 H 0.398906 0.273268 0.493472 0.078 Uiso 1 1 calc R U . . .
H19 H 0.417157 0.097165 0.502269 0.078 Uiso 1 1 calc R U . . .
C5 C 0.48319(15) 0.2345(5) 0.4343(3) 0.0642(10) Uani 1 1 d . . . . .
H11 H 0.484935 0.327553 0.380543 0.077 Uiso 1 1 calc R U . . .
H20 H 0.503131 0.151418 0.388353 0.077 Uiso 1 1 calc R U . . .
C6 C 0.51706(15) 0.2651(6) 0.5625(3) 0.0661(11) Uani 1 1 d . . . . .
H22 H 0.497002 0.347670 0.608763 0.079 Uiso 1 1 calc R U . . .
H21 H 0.515577 0.171755 0.616072 0.079 Uiso 1 1 calc R U . . .
C7 C 0.58157(15) 0.3109(6) 0.5481(4) 0.0655(11) Uani 1 1 d . . . . .
H9 H 0.583153 0.405681 0.496515 0.079 Uiso 1 1 calc R U . . .
H10 H 0.601555 0.229398 0.500373 0.079 Uiso 1 1 calc R U . . .
C8 C 0.61493(14) 0.3373(5) 0.6772(4) 0.0629(10) Uani 1 1 d . . . . .
H23 H 0.594458 0.417548 0.725387 0.075 Uiso 1 1 calc R U . . .
H8 H 0.613664 0.241958 0.728180 0.075 Uiso 1 1 calc R U . . .
C9 C 0.67926(15) 0.3854(5) 0.6648(4) 0.0619(10) Uani 1 1 d . . . . .
H24 H 0.699394 0.307674 0.613253 0.074 Uiso 1 1 calc R U . . .
H25 H 0.680555 0.483521 0.617686 0.074 Uiso 1 1 calc R U . . .
C10 C 0.71266(15) 0.4040(5) 0.7946(4) 0.0610(10) Uani 1 1 d . . . . .
H26 H 0.691255 0.477279 0.848030 0.073 Uiso 1 1 calc R U . . .
H27 H 0.713236 0.304255 0.839559 0.073 Uiso 1 1 calc R U . . .
C11 C 0.77593(15) 0.4604(5) 0.7830(4) 0.0571(9) Uani 1 1 d . . . . .
H28 H 0.796433 0.393543 0.722481 0.069 Uiso 1 1 calc R U . . .
H7 H 0.775476 0.565292 0.747239 0.069 Uiso 1 1 calc R U . . .
C12 C 0.80933(16) 0.4609(5) 0.9118(4) 0.0711(12) Uani 1 1 d . . . . .
H29 H 0.786798 0.518994 0.974934 0.085 Uiso 1 1 calc R U . . .
H30 H 0.813412 0.354505 0.943358 0.085 Uiso 1 1 calc R U . . .
C13 C 0.88804(14) 0.6637(4) 0.9548(3) 0.0451(8) Uani 1 1 d . . . . .
C14 C 0.98454(18) 0.8081(4) 0.9659(4) 0.0752(12) Uani 1 1 d . . . . .
H3 H 0.967694 0.904256 0.933736 0.113 Uiso 1 1 calc R U . . .
H33 H 1.022990 0.792899 0.929469 0.113 Uiso 1 1 calc R U . . .
H2 H 0.988648 0.812278 1.059612 0.113 Uiso 1 1 calc R U . . .
C15 C 0.8537(2) 0.7771(5) 1.0303(4) 0.0755(12) Uani 1 1 d . . . . .
H4 H 0.880453 0.838645 1.084183 0.113 Uiso 1 1 calc R U . . .
H6 H 0.826548 0.722405 1.084656 0.113 Uiso 1 1 calc R U . . .
H5 H 0.831608 0.844214 0.971101 0.113 Uiso 1 1 calc R U . . .
C16 C 0.91450(16) 0.4604(4) 0.8405(4) 0.0556(9) Uani 1 1 d . . . . .
H32 H 0.912685 0.366103 0.795523 0.067 Uiso 1 1 calc R U . . .
C17 C 0.96234(15) 0.5518(4) 0.8567(4) 0.0539(9) Uani 1 1 d . . . . .
H31 H 1.000148 0.532948 0.825700 0.065 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
N1 C13 1.324(4) . ?
N1 C16 1.362(5) . ?
N1 C12 1.472(4) . ?
N2 C13 1.329(4) . ?
N2 C17 1.362(4) . ?
N2 C14 1.468(4) . ?
C1 C2 1.509(5) . ?
C1 H14 0.9600 . ?
C1 H15 0.9600 . ?
C1 H1 0.9600 . ?
C2 C3 1.509(5) . ?
C2 H12 0.9700 . ?
C2 H13 0.9700 . ?
C3 C4 1.510(5) . ?
C3 H16 0.9700 . ?
C3 H17 0.9700 . ?
C4 C5 1.503(5) . ?
C4 H18 0.9700 . ?
C4 H19 0.9700 . ?
C5 C6 1.516(4) . ?
C5 H11 0.9700 . ?
C5 H20 0.9700 . ?
C6 C7 1.513(5) . ?
C6 H22 0.9700 . ?
C6 H21 0.9700 . ?
C7 C8 1.513(5) . ?
C7 H9 0.9700 . ?
C7 H10 0.9700 . ?
C8 C9 1.511(5) . ?
C8 H23 0.9700 . ?
C8 H8 0.9700 . ?
C9 C10 1.511(5) . ?
C9 H24 0.9700 . ?
C9 H25 0.9700 . ?
C10 C11 1.509(5) . ?
C10 H26 0.9700 . ?
C10 H27 0.9700 . ?
C11 C12 1.494(5) . ?
C11 H28 0.9700 . ?
C11 H7 0.9700 . ?
C12 H29 0.9700 . ?
C12 H30 0.9700 . ?
C13 C15 1.475(5) . ?
C14 H3 0.9600 . ?
C14 H33 0.9600 . ?
C14 H2 0.9600 . ?
C15 H4 0.9600 . ?
C15 H6 0.9600 . ?
C15 H5 0.9600 . ?
C16 C17 1.336(5) . ?
C16 H32 0.9300 . ?
C17 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C16 109.2(3) . . ?
C13 N1 C12 127.4(3) . . ?
C16 N1 C12 123.3(3) . . ?
C13 N2 C17 109.2(3) . . ?
C13 N2 C14 126.2(3) . . ?
C17 N2 C14 124.6(3) . . ?
C2 C1 H14 109.5 . . ?
C2 C1 H15 109.5 . . ?
H14 C1 H15 109.5 . . ?
C2 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
H15 C1 H1 109.5 . . ?
C1 C2 C3 113.5(3) . . ?
C1 C2 H12 108.9 . . ?
C3 C2 H12 108.9 . . ?
C1 C2 H13 108.9 . . ?
C3 C2 H13 108.9 . . ?
H12 C2 H13 107.7 . . ?
C2 C3 C4 115.0(3) . . ?
C2 C3 H16 108.5 . . ?
C4 C3 H16 108.5 . . ?
C2 C3 H17 108.5 . . ?
C4 C3 H17 108.5 . . ?
H16 C3 H17 107.5 . . ?
C5 C4 C3 114.3(3) . . ?
C5 C4 H18 108.7 . . ?
C3 C4 H18 108.7 . . ?
C5 C4 H19 108.7 . . ?
C3 C4 H19 108.7 . . ?
H18 C4 H19 107.6 . . ?
C4 C5 C6 114.7(3) . . ?
C4 C5 H11 108.6 . . ?
C6 C5 H11 108.6 . . ?
C4 C5 H20 108.6 . . ?
C6 C5 H20 108.6 . . ?
H11 C5 H20 107.6 . . ?
C7 C6 C5 114.5(3) . . ?
C7 C6 H22 108.6 . . ?
C5 C6 H22 108.6 . . ?
C7 C6 H21 108.6 . . ?
C5 C6 H21 108.6 . . ?
H22 C6 H21 107.6 . . ?
C6 C7 C8 113.7(3) . . ?
C6 C7 H9 108.8 . . ?
C8 C7 H9 108.8 . . ?
C6 C7 H10 108.8 . . ?
C8 C7 H10 108.8 . . ?
H9 C7 H10 107.7 . . ?
C9 C8 C7 114.5(3) . . ?
C9 C8 H23 108.6 . . ?
C7 C8 H23 108.6 . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
H23 C8 H8 107.6 . . ?
C10 C9 C8 113.8(3) . . ?
C10 C9 H24 108.8 . . ?
C8 C9 H24 108.8 . . ?
C10 C9 H25 108.8 . . ?
C8 C9 H25 108.8 . . ?
H24 C9 H25 107.7 . . ?
C11 C10 C9 114.0(3) . . ?
C11 C10 H26 108.8 . . ?
C9 C10 H26 108.8 . . ?
C11 C10 H27 108.8 . . ?
C9 C10 H27 108.8 . . ?
H26 C10 H27 107.7 . . ?
C12 C11 C10 112.2(3) . . ?
C12 C11 H28 109.2 . . ?
C10 C11 H28 109.2 . . ?
C12 C11 H7 109.2 . . ?
C10 C11 H7 109.2 . . ?
H28 C11 H7 107.9 . . ?
N1 C12 C11 111.9(3) . . ?
N1 C12 H29 109.2 . . ?
C11 C12 H29 109.2 . . ?
N1 C12 H30 109.2 . . ?
C11 C12 H30 109.2 . . ?
H29 C12 H30 107.9 . . ?
N1 C13 N2 107.3(3) . . ?
N1 C13 C15 127.6(3) . . ?
N2 C13 C15 125.1(3) . . ?
N2 C14 H3 109.5 . . ?
N2 C14 H33 109.5 . . ?
H3 C14 H33 109.5 . . ?
N2 C14 H2 109.5 . . ?
H3 C14 H2 109.5 . . ?
H33 C14 H2 109.5 . . ?
C13 C15 H4 109.5 . . ?
C13 C15 H6 109.5 . . ?
H4 C15 H6 109.5 . . ?
C13 C15 H5 109.5 . . ?
H4 C15 H5 109.5 . . ?
H6 C15 H5 109.5 . . ?
C17 C16 N1 107.2(3) . . ?
C17 C16 H32 126.4 . . ?
N1 C16 H32 126.4 . . ?
C16 C17 N2 107.0(3) . . ?
C16 C17 H31 126.5 . . ?
N2 C17 H31 126.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 179.8(4) . . . . ?
C3 C4 C5 C6 -179.6(4) . . . . ?
C4 C5 C6 C7 -179.6(4) . . . . ?
C5 C6 C7 C8 -178.7(4) . . . . ?
C6 C7 C8 C9 -179.2(4) . . . . ?
C7 C8 C9 C10 -177.3(4) . . . . ?
C8 C9 C10 C11 -176.8(4) . . . . ?
C9 C10 C11 C12 -173.9(4) . . . . ?
C13 N1 C12 C11 112.4(4) . . . . ?
C16 N1 C12 C11 -71.2(5) . . . . ?
C10 C11 C12 N1 -174.2(3) . . . . ?
C16 N1 C13 N2 -0.1(4) . . . . ?
C12 N1 C13 N2 176.8(3) . . . . ?
C16 N1 C13 C15 180.0(4) . . . . ?
C12 N1 C13 C15 -3.2(6) . . . . ?
C17 N2 C13 N1 -0.2(4) . . . . ?
C14 N2 C13 N1 179.7(3) . . . . ?
C17 N2 C13 C15 179.7(3) . . . . ?
C14 N2 C13 C15 -0.3(5) . . . . ?
C13 N1 C16 C17 0.3(4) . . . . ?
C12 N1 C16 C17 -176.6(3) . . . . ?
N1 C16 C17 N2 -0.5(4) . . . . ?
C13 N2 C17 C16 0.4(4) . . . . ?
C14 N2 C17 C16 -179.5(3) . . . . ?

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.060

