# 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 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. 
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data_jlgld110215
_database_code_depnum_ccdc_archive 'CCDC 1830443'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-23 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         'C22 H35 N2, Br'
_chemical_formula_sum            'C22 H35 Br N2'
_chemical_formula_weight         407.43

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                   20.4743(10)
_cell_length_b                   14.5386(6)
_cell_length_c                   7.5277(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.385(3)
_cell_angle_gamma                90
_cell_volume                     2204.05(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    52865
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.872
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58705
_exptl_absorpt_correction_T_max  0.75162
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16002
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.011
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5009
_reflns_number_gt                3628
_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       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON 2003 (Spek, 2003)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0777P)²+0.6219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5009
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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 1.04198(17) 0.7984(2) 0.0732(5) 0.0240(8) Uani 1 1 d . . . . .
C2 C 1.09495(19) 0.8526(3) 0.0453(5) 0.0309(9) Uani 1 1 d . . . . .
H2 H 1.0928 0.9177 0.0547 0.037 Uiso 1 1 calc R U . . .
C3 C 1.15084(19) 0.8110(3) 0.0040(5) 0.0312(9) Uani 1 1 d . . . . .
H3 H 1.1867 0.8484 -0.0171 0.037 Uiso 1 1 calc R U . . .
C4 C 1.15626(19) 0.7159(3) -0.0079(5) 0.0283(9) Uani 1 1 d . . . . .
C5 C 1.10194(19) 0.6638(3) 0.0162(5) 0.0300(9) Uani 1 1 d . . . . .
H5 H 1.1037 0.5989 0.0036 0.036 Uiso 1 1 calc R U . . .
C6 C 1.04502(19) 0.7036(2) 0.0581(5) 0.0263(8) Uani 1 1 d . . . . .
H6 H 1.0086 0.6664 0.0762 0.032 Uiso 1 1 calc R U . . .
C7 C 1.2188(2) 0.6716(3) -0.0421(6) 0.0412(11) Uani 1 1 d . . . . .
H7A H 1.2523 0.6728 0.0689 0.062 Uiso 1 1 calc R U . . .
H7B H 1.2355 0.7053 -0.1375 0.062 Uiso 1 1 calc R U . . .
H7C H 1.2097 0.6077 -0.0801 0.062 Uiso 1 1 calc R U . . .
C8 C 0.92707(18) 0.7995(3) 0.1277(5) 0.0285(9) Uani 1 1 d . . . . .
H8 H 0.9162 0.7382 0.0900 0.034 Uiso 1 1 calc R U . . .
C9 C 0.9807(2) 0.9307(2) 0.1857(6) 0.0297(9) Uani 1 1 d . . . . .
H9 H 1.0142 0.9765 0.1959 0.036 Uiso 1 1 calc R U . . .
C10 C 0.9196(2) 0.9400(3) 0.2287(6) 0.0318(9) Uani 1 1 d . . . . .
H10 H 0.9024 0.9938 0.2750 0.038 Uiso 1 1 calc R U . . .
C11 C 0.81966(19) 0.8356(3) 0.2239(6) 0.0322(9) Uani 1 1 d . . . . .
H11A H 0.8164 0.8513 0.3499 0.039 Uiso 1 1 calc R U . . .
H11B H 0.8119 0.7686 0.2080 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7661(2) 0.8872(3) 0.0960(6) 0.0386(10) Uani 1 1 d . . . . .
H12A H 0.7700 0.8735 -0.0304 0.046 Uiso 1 1 calc R U . . .
H12B H 0.7722 0.9542 0.1155 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6969(2) 0.8587(3) 0.1287(6) 0.0425(11) Uani 1 1 d . . . . .
H13A H 0.6630 0.8845 0.0308 0.051 Uiso 1 1 calc R U . . .
H13B H 0.6933 0.7908 0.1216 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6814(2) 0.8900(3) 0.3088(6) 0.0374(10) Uani 1 1 d . . . . .
H14A H 0.6840 0.9579 0.3155 0.045 Uiso 1 1 calc R U . . .
H14B H 0.7155 0.8649 0.4072 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6128(2) 0.8592(3) 0.3381(6) 0.0365(10) Uani 1 1 d . . . . .
H15A H 0.5790 0.8829 0.2378 0.044 Uiso 1 1 calc R U . . .
H15B H 0.6107 0.7912 0.3340 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5957(2) 0.8916(3) 0.5150(6) 0.0371(10) Uani 1 1 d . . . . .
H16A H 0.5966 0.9597 0.5178 0.044 Uiso 1 1 calc R U . . .
H16B H 0.6302 0.8692 0.6153 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5275(2) 0.8586(3) 0.5463(6) 0.0373(10) Uani 1 1 d . . . . .
H17A H 0.4931 0.8801 0.4450 0.045 Uiso 1 1 calc R U . . .
H17B H 0.5268 0.7905 0.5453 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5097(2) 0.8921(3) 0.7224(6) 0.0355(10) Uani 1 1 d . . . . .
H18A H 0.5109 0.9601 0.7239 0.043 Uiso 1 1 calc R U . . .
H18B H 0.5439 0.8700 0.8236 0.043 Uiso 1 1 calc R U . . .
C19 C 0.4419(2) 0.8606(3) 0.7537(6) 0.0396(11) Uani 1 1 d . . . . .
H19A H 0.4405 0.7925 0.7514 0.048 Uiso 1 1 calc R U . . .
H19B H 0.4076 0.8832 0.6535 0.048 Uiso 1 1 calc R U . . .
C20 C 0.4252(2) 0.8940(3) 0.9319(6) 0.0356(10) Uani 1 1 d . . . . .
H20A H 0.4599 0.8718 1.0317 0.043 Uiso 1 1 calc R U . . .
H20B H 0.4265 0.9621 0.9335 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3581(2) 0.8629(3) 0.9670(6) 0.0441(11) Uani 1 1 d . . . . .
H21A H 0.3564 0.7948 0.9647 0.053 Uiso 1 1 calc R U . . .
H21B H 0.3231 0.8858 0.8686 0.053 Uiso 1 1 calc R U . . .
C22 C 0.3432(2) 0.8965(4) 1.1474(7) 0.0508(13) Uani 1 1 d . . . . .
H22A H 0.3766 0.8723 1.2458 0.076 Uiso 1 1 calc R U . . .
H22B H 0.2991 0.8750 1.1619 0.076 Uiso 1 1 calc R U . . .
H22C H 0.3442 0.9639 1.1502 0.076 Uiso 1 1 calc R U . . .
N1 N 0.98474(15) 0.8411(2) 0.1236(4) 0.0240(7) Uani 1 1 d . . . . .
N2 N 0.88714(15) 0.8575(2) 0.1930(4) 0.0274(7) Uani 1 1 d . . . . .
Br1 Br 0.87231(2) 0.92087(3) 0.69665(6) 0.03520(17) 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 C6 1.385(5) . ?
C1 C2 1.387(5) . ?
C1 N1 1.436(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 C7 1.498(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.329(5) . ?
C8 N1 1.332(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.353(6) . ?
C9 N1 1.392(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.375(5) . ?
C10 H10 0.9500 . ?
C11 N2 1.477(5) . ?
C11 C12 1.520(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.539(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.529(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.511(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.535(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.517(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.515(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.525(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.3(3) . . ?
C6 C1 N1 120.2(3) . . ?
C2 C1 N1 119.5(3) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 122.0(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C7 121.3(4) . . ?
C3 C4 C7 121.3(4) . . ?
C4 C5 C6 121.9(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 109.1(3) . . ?
N2 C8 H8 125.4 . . ?
N1 C8 H8 125.4 . . ?
C10 C9 N1 106.7(3) . . ?
C10 C9 H9 126.6 . . ?
N1 C9 H9 126.6 . . ?
C9 C10 N2 107.5(3) . . ?
C9 C10 H10 126.2 . . ?
N2 C10 H10 126.2 . . ?
N2 C11 C12 112.5(3) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 110.3(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 114.1(4) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 112.7(4) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 113.6(4) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.5(4) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.7(3) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 114.1(4) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113.4(4) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 114.4(4) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 113.1(4) . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C9 108.1(3) . . ?
C8 N1 C1 125.4(3) . . ?
C9 N1 C1 126.5(3) . . ?
C8 N2 C10 108.5(3) . . ?
C8 N2 C11 125.2(3) . . ?
C10 N2 C11 126.2(3) . . ?

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
C6 C1 C2 C3 -0.5(6) . . . . ?
N1 C1 C2 C3 177.5(3) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C3 C4 C5 2.6(6) . . . . ?
C2 C3 C4 C7 -176.3(4) . . . . ?
C3 C4 C5 C6 -2.7(6) . . . . ?
C7 C4 C5 C6 176.3(4) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
N1 C1 C6 C5 -177.5(3) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
N1 C9 C10 N2 -0.1(5) . . . . ?
N2 C11 C12 C13 177.6(3) . . . . ?
C11 C12 C13 C14 68.3(5) . . . . ?
C12 C13 C14 C15 -179.1(4) . . . . ?
C13 C14 C15 C16 -178.6(4) . . . . ?
C14 C15 C16 C17 -178.5(4) . . . . ?
C15 C16 C17 C18 -179.2(4) . . . . ?
C16 C17 C18 C19 179.4(4) . . . . ?
C17 C18 C19 C20 179.4(4) . . . . ?
C18 C19 C20 C21 -179.5(4) . . . . ?
C19 C20 C21 C22 179.3(4) . . . . ?
N2 C8 N1 C9 -1.4(4) . . . . ?
N2 C8 N1 C1 175.4(3) . . . . ?
C10 C9 N1 C8 0.9(5) . . . . ?
C10 C9 N1 C1 -175.9(3) . . . . ?
C6 C1 N1 C8 -12.7(6) . . . . ?
C2 C1 N1 C8 169.3(4) . . . . ?
C6 C1 N1 C9 163.5(4) . . . . ?
C2 C1 N1 C9 -14.5(6) . . . . ?
N1 C8 N2 C10 1.3(4) . . . . ?
N1 C8 N2 C11 -177.9(3) . . . . ?
C9 C10 N2 C8 -0.8(5) . . . . ?
C9 C10 N2 C11 178.5(4) . . . . ?
C12 C11 N2 C8 -111.8(4) . . . . ?
C12 C11 N2 C10 69.1(5) . . . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_jlgld110217
_database_code_depnum_ccdc_archive 'CCDC 1830444'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-23 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         'C21 H33 N2, F6 P'
_chemical_formula_sum            'C21 H33 F6 N2 P'
_chemical_formula_weight         458.46

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   8.3458(8)
_cell_length_b                   10.7404(11)
_cell_length_c                   26.252(3)
_cell_angle_alpha                79.541(2)
_cell_angle_beta                 87.329(2)
_cell_angle_gamma                89.045(2)
_cell_volume                     2311.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5592
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      28.94

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34173
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12278
_reflns_number_gt                6899
_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-2014/7 (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)+(0.0943P)²+1.3341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12278
_refine_ls_number_parameters     543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2058
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.9209(3) 0.6431(3) 0.43889(11) 0.0235(6) Uani 1 1 d . . . . .
C2 C 0.9742(3) 0.7285(3) 0.46749(12) 0.0281(6) Uani 1 1 d . . . . .
H2 H 1.0495 0.7917 0.4526 0.034 Uiso 1 1 calc R U . . .
C3 C 0.9163(4) 0.7211(3) 0.51837(12) 0.0315(7) Uani 1 1 d . . . . .
H3 H 0.9504 0.7804 0.5383 0.038 Uiso 1 1 calc R U . . .
C4 C 0.8097(3) 0.6279(3) 0.53997(11) 0.0309(7) Uani 1 1 d . . . . .
H4 H 0.7705 0.6230 0.5748 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7593(4) 0.5413(3) 0.51106(11) 0.0302(7) Uani 1 1 d . . . . .
H5 H 0.6869 0.4764 0.5263 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8143(3) 0.5490(3) 0.45974(11) 0.0270(6) Uani 1 1 d . . . . .
H6 H 0.7790 0.4907 0.4395 0.032 Uiso 1 1 calc R U . . .
C7 C 0.9958(3) 0.5592(3) 0.35871(10) 0.0225(6) Uani 1 1 d . . . . .
H7 H 0.9748 0.4724 0.3718 0.027 Uiso 1 1 calc R U . . .
C8 C 1.0213(4) 0.7649(3) 0.35310(12) 0.0334(7) Uani 1 1 d . . . . .
H8 H 1.0205 0.8470 0.3618 0.040 Uiso 1 1 calc R U . . .
C9 C 1.0649(4) 0.7355(3) 0.30703(12) 0.0349(7) Uani 1 1 d . . . . .
H9 H 1.1010 0.7931 0.2770 0.042 Uiso 1 1 calc R U . . .
C10 C 1.0790(4) 0.5351(3) 0.26876(11) 0.0315(7) Uani 1 1 d . . . . .
H10A H 1.0743 0.4434 0.2831 0.038 Uiso 1 1 calc R U . . .
H10B H 1.1884 0.5542 0.2533 0.038 Uiso 1 1 calc R U . . .
C11 C 0.9585(4) 0.5673(3) 0.22698(11) 0.0301(6) Uani 1 1 d . . . . .
H11A H 0.9662 0.6584 0.2115 0.036 Uiso 1 1 calc R U . . .
H11B H 0.8488 0.5516 0.2426 0.036 Uiso 1 1 calc R U . . .
C12 C 0.9873(4) 0.4891(3) 0.18487(12) 0.0336(7) Uani 1 1 d . . . . .
H12A H 0.9831 0.3983 0.2009 0.040 Uiso 1 1 calc R U . . .
H12B H 1.0966 0.5066 0.1691 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8677(4) 0.5145(3) 0.14224(12) 0.0332(7) Uani 1 1 d . . . . .
H13A H 0.7580 0.4988 0.1579 0.040 Uiso 1 1 calc R U . . .
H13B H 0.8737 0.6047 0.1255 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8971(4) 0.4327(3) 0.10135(12) 0.0372(8) Uani 1 1 d . . . . .
H14A H 0.8975 0.3428 0.1187 0.045 Uiso 1 1 calc R U . . .
H14B H 1.0050 0.4518 0.0847 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7753(4) 0.4498(3) 0.05935(12) 0.0355(7) Uani 1 1 d . . . . .
H15A H 0.6675 0.4289 0.0757 0.043 Uiso 1 1 calc R U . . .
H15B H 0.7735 0.5398 0.0422 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8096(5) 0.3686(3) 0.01861(12) 0.0403(8) Uani 1 1 d . . . . .
H16A H 0.8168 0.2790 0.0362 0.048 Uiso 1 1 calc R U . . .
H16B H 0.9156 0.3922 0.0014 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6869(4) 0.3786(3) -0.02268(12) 0.0392(8) Uani 1 1 d . . . . .
H17A H 0.5814 0.3522 -0.0057 0.047 Uiso 1 1 calc R U . . .
H17B H 0.6772 0.4684 -0.0397 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7262(5) 0.2997(4) -0.06384(13) 0.0438(8) Uani 1 1 d . . . . .
H18A H 0.8302 0.3284 -0.0814 0.053 Uiso 1 1 calc R U . . .
H18B H 0.7402 0.2106 -0.0465 0.053 Uiso 1 1 calc R U . . .
C19 C 0.6036(5) 0.3039(4) -0.10464(13) 0.0456(9) Uani 1 1 d . . . . .
H19A H 0.4998 0.2737 -0.0873 0.055 Uiso 1 1 calc R U . . .
H19B H 0.5882 0.3930 -0.1218 0.055 Uiso 1 1 calc R U . . .
C20 C 0.6477(6) 0.2257(4) -0.14555(14) 0.0572(11) Uani 1 1 d . . . . .
H20A H 0.6675 0.1374 -0.1282 0.069 Uiso 1 1 calc R U . . .
H20B H 0.7493 0.2583 -0.1637 0.069 Uiso 1 1 calc R U . . .
C21 C 0.5230(7) 0.2250(5) -0.18546(16) 0.0752(15) Uani 1 1 d . . . . .
H21A H 0.4267 0.1818 -0.1687 0.113 Uiso 1 1 calc R U . . .
H21B H 0.5661 0.1803 -0.2126 0.113 Uiso 1 1 calc R U . . .
H21C H 0.4956 0.3123 -0.2010 0.113 Uiso 1 1 calc R U . . .
C22 C 0.4236(3) 0.9113(3) 0.44062(11) 0.0237(6) Uani 1 1 d . . . . .
C23 C 0.4784(4) 0.7991(3) 0.46929(12) 0.0291(6) Uani 1 1 d . . . . .
H23 H 0.5566 0.7490 0.4547 0.035 Uiso 1 1 calc R U . . .
C24 C 0.4175(4) 0.7606(3) 0.51974(12) 0.0308(7) Uani 1 1 d . . . . .
H24 H 0.4526 0.6829 0.5396 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3062(4) 0.8348(3) 0.54110(12) 0.0304(7) Uani 1 1 d . . . . .
H25 H 0.2643 0.8081 0.5756 0.036 Uiso 1 1 calc R U . . .
C26 C 0.2558(4) 0.9482(3) 0.51223(12) 0.0329(7) Uani 1 1 d . . . . .
H26 H 0.1809 1.0000 0.5273 0.039 Uiso 1 1 calc R U . . .
C27 C 0.3132(3) 0.9871(3) 0.46152(12) 0.0282(6) Uani 1 1 d . . . . .
H27 H 0.2773 1.0645 0.4416 0.034 Uiso 1 1 calc R U . . .
C28 C 0.4942(3) 1.0669(3) 0.36076(11) 0.0244(6) Uani 1 1 d . . . . .
H28 H 0.4660 1.1419 0.3736 0.029 Uiso 1 1 calc R U . . .
C29 C 0.5352(4) 0.8663(3) 0.35558(12) 0.0343(7) Uani 1 1 d . . . . .
H29 H 0.5400 0.7766 0.3644 0.041 Uiso 1 1 calc R U . . .
C30 C 0.5768(4) 0.9375(3) 0.30948(12) 0.0357(7) Uani 1 1 d . . . . .
H30 H 0.6176 0.9070 0.2796 0.043 Uiso 1 1 calc R U . . .
C31 C 0.5728(4) 1.1720(3) 0.27101(11) 0.0327(7) Uani 1 1 d . . . . .
H31A H 0.6860 1.1744 0.2578 0.039 Uiso 1 1 calc R U . . .
H31B H 0.5498 1.2508 0.2846 0.039 Uiso 1 1 calc R U . . .
C32 C 0.4641(4) 1.1654(3) 0.22702(11) 0.0303(7) Uani 1 1 d . . . . .
H32A H 0.3515 1.1566 0.2407 0.036 Uiso 1 1 calc R U . . .
H32B H 0.4927 1.0900 0.2116 0.036 Uiso 1 1 calc R U . . .
C33 C 0.4792(5) 1.2833(3) 0.18548(12) 0.0391(8) Uani 1 1 d . . . . .
H33A H 0.5899 1.2877 0.1700 0.047 Uiso 1 1 calc R U . . .
H33B H 0.4610 1.3588 0.2018 0.047 Uiso 1 1 calc R U . . .
C34 C 0.3610(5) 1.2871(3) 0.14225(13) 0.0425(8) Uani 1 1 d . . . . .
H34A H 0.2518 1.2718 0.1583 0.051 Uiso 1 1 calc R U . . .
H34B H 0.3616 1.3733 0.1210 0.051 Uiso 1 1 calc R U . . .
C35 C 0.3951(4) 1.1925(3) 0.10673(12) 0.0369(7) Uani 1 1 d . . . . .
H35A H 0.3868 1.1058 0.1273 0.044 Uiso 1 1 calc R U . . .
H35B H 0.5064 1.2039 0.0920 0.044 Uiso 1 1 calc R U . . .
C36 C 0.2807(4) 1.2060(3) 0.06257(12) 0.0376(8) Uani 1 1 d . . . . .
H36A H 0.1700 1.1923 0.0776 0.045 Uiso 1 1 calc R U . . .
H36B H 0.2864 1.2939 0.0431 0.045 Uiso 1 1 calc R U . . .
C37 C 0.3129(4) 1.1162(3) 0.02487(12) 0.0381(8) Uani 1 1 d . . . . .
H37A H 0.3062 1.0281 0.0442 0.046 Uiso 1 1 calc R U . . .
H37B H 0.4237 1.1294 0.0099 0.046 Uiso 1 1 calc R U . . .
C38 C 0.1976(4) 1.1322(3) -0.01910(12) 0.0404(8) Uani 1 1 d . . . . .
H38A H 0.0869 1.1192 -0.0040 0.049 Uiso 1 1 calc R U . . .
H38B H 0.2045 1.2203 -0.0384 0.049 Uiso 1 1 calc R U . . .
C39 C 0.2284(5) 1.0430(3) -0.05691(13) 0.0422(8) Uani 1 1 d . . . . .
H39A H 0.2191 0.9548 -0.0378 0.051 Uiso 1 1 calc R U . . .
H39B H 0.3399 1.0546 -0.0714 0.051 Uiso 1 1 calc R U . . .
C40 C 0.1157(5) 1.0609(4) -0.10134(13) 0.0437(8) Uani 1 1 d . . . . .
H40A H 0.0041 1.0512 -0.0868 0.052 Uiso 1 1 calc R U . . .
H40B H 0.1267 1.1486 -0.1209 0.052 Uiso 1 1 calc R U . . .
C41 C 0.1434(5) 0.9705(4) -0.13863(15) 0.0535(10) Uani 1 1 d . . . . .
H41A H 0.1310 0.8828 -0.1193 0.064 Uiso 1 1 calc R U . . .
H41B H 0.2553 0.9795 -0.1530 0.064 Uiso 1 1 calc R U . . .
C42 C 0.0315(7) 0.9903(5) -0.18304(17) 0.0788(16) Uani 1 1 d . . . . .
H42A H -0.0798 0.9855 -0.1693 0.118 Uiso 1 1 calc R U . . .
H42B H 0.0514 0.9245 -0.2041 0.118 Uiso 1 1 calc R U . . .
H42C H 0.0505 1.0738 -0.2046 0.118 Uiso 1 1 calc R U . . .
N1 N 0.9778(3) 0.6537(2) 0.38561(9) 0.0229(5) Uani 1 1 d . . . . .
N2 N 1.0478(3) 0.6071(2) 0.31093(9) 0.0253(5) Uani 1 1 d . . . . .
N3 N 0.4840(3) 0.9491(2) 0.38778(9) 0.0244(5) Uani 1 1 d . . . . .
N4 N 0.5498(3) 1.0620(2) 0.31322(9) 0.0267(5) Uani 1 1 d . . . . .
F1 F 0.6654(2) 0.62121(19) 0.32222(9) 0.0500(6) Uani 1 1 d . . . . .
F2 F 0.5646(3) 0.4825(2) 0.27732(8) 0.0578(6) Uani 1 1 d . . . . .
F3 F 0.3985(3) 0.4092(2) 0.34464(10) 0.0782(9) Uani 1 1 d . . . . .
F4 F 0.4974(3) 0.5486(2) 0.38996(8) 0.0565(6) Uani 1 1 d . . . . .
F5 F 0.4039(3) 0.6196(2) 0.31161(10) 0.0651(7) Uani 1 1 d . . . . .
F6 F 0.6611(4) 0.4133(2) 0.35603(11) 0.0778(8) Uani 1 1 d . . . . .
F7 F 0.9263(4) 0.7842(2) 0.72322(9) 0.0753(8) Uani 1 1 d . . . . .
F8 F 1.0903(3) 0.9456(3) 0.68913(13) 0.0855(9) Uani 1 1 d . . . . .
F9 F 0.9997(4) 0.9456(2) 0.61129(8) 0.0732(8) Uani 1 1 d . . . . .
F10 F 0.8344(4) 0.7858(2) 0.64496(14) 0.0940(10) Uani 1 1 d . . . . .
F11 F 0.8302(3) 0.9657(2) 0.67671(10) 0.0596(7) Uani 1 1 d . . . . .
F12 F 1.0923(4) 0.7621(2) 0.65723(11) 0.0884(10) Uani 1 1 d . . . . .
P1 P 0.53127(9) 0.51463(7) 0.33318(3) 0.02712(18) Uani 1 1 d . . . . .
P2 P 0.96369(9) 0.86250(7) 0.66784(3) 0.02641(18) 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 C6 1.378(4) . ?
C1 C2 1.378(4) . ?
C1 N1 1.441(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.322(4) . ?
C7 N1 1.340(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.337(4) . ?
C8 N1 1.380(4) . ?
C8 H8 0.9500 . ?
C9 N2 1.374(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.472(4) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.514(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.511(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.510(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.508(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.512(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.380(4) . ?
C22 C23 1.383(4) . ?
C22 N3 1.442(3) . ?
C23 C24 1.389(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 N4 1.321(4) . ?
C28 N3 1.335(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.343(4) . ?
C29 N3 1.384(4) . ?
C29 H29 0.9500 . ?
C30 N4 1.374(4) . ?
C30 H30 0.9500 . ?
C31 N4 1.474(4) . ?
C31 C32 1.514(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.516(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.533(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.514(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.521(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.515(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.521(5) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.511(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.516(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.507(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.510(6) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
F1 P1 1.593(2) . ?
F2 P1 1.578(2) . ?
F3 P1 1.577(2) . ?
F4 P1 1.609(2) . ?
F5 P1 1.583(2) . ?
F6 P1 1.582(2) . ?
F7 P2 1.562(2) . ?
F8 P2 1.579(3) . ?
F9 P2 1.605(2) . ?
F10 P2 1.573(3) . ?
F11 P2 1.598(2) . ?
F12 P2 1.561(2) . ?

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
C6 C1 C2 121.8(3) . . ?
C6 C1 N1 119.4(3) . . ?
C2 C1 N1 118.8(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 N1 108.6(2) . . ?
N2 C7 H7 125.7 . . ?
N1 C7 H7 125.7 . . ?
C9 C8 N1 107.1(3) . . ?
C9 C8 H8 126.4 . . ?
N1 C8 H8 126.4 . . ?
C8 C9 N2 107.7(3) . . ?
C8 C9 H9 126.1 . . ?
N2 C9 H9 126.1 . . ?
N2 C10 C11 111.7(2) . . ?
N2 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 111.3(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 114.1(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 112.9(3) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 114.9(3) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 113.6(3) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 115.2(3) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 114.3(3) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 115.7(3) . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C17 C18 H18B 108.4 . . ?
H18A C18 H18B 107.4 . . ?
C20 C19 C18 114.3(4) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 114.9(4) . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.4(3) . . ?
C27 C22 N3 119.7(3) . . ?
C23 C22 N3 118.9(2) . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 118.6(3) . . ?
C22 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
N4 C28 N3 108.8(2) . . ?
N4 C28 H28 125.6 . . ?
N3 C28 H28 125.6 . . ?
C30 C29 N3 106.6(3) . . ?
C30 C29 H29 126.7 . . ?
N3 C29 H29 126.7 . . ?
C29 C30 N4 107.8(3) . . ?
C29 C30 H30 126.1 . . ?
N4 C30 H30 126.1 . . ?
N4 C31 C32 111.2(2) . . ?
N4 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
N4 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 111.1(3) . . ?
C31 C32 H32A 109.4 . . ?
C33 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C33 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C32 C33 C34 113.3(3) . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
C34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C35 C34 C33 115.1(3) . . ?
C35 C34 H34A 108.5 . . ?
C33 C34 H34A 108.5 . . ?
C35 C34 H34B 108.5 . . ?
C33 C34 H34B 108.5 . . ?
H34A C34 H34B 107.5 . . ?
C34 C35 C36 112.9(3) . . ?
C34 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
C34 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 115.0(3) . . ?
C37 C36 H36A 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C37 C36 H36B 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C36 C37 C38 114.0(3) . . ?
C36 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
C36 C37 H37B 108.8 . . ?
C38 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C39 C38 C37 114.4(3) . . ?
C39 C38 H38A 108.7 . . ?
C37 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C37 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C38 C39 C40 114.4(3) . . ?
C38 C39 H39A 108.7 . . ?
C40 C39 H39A 108.7 . . ?
C38 C39 H39B 108.7 . . ?
C40 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C41 C40 C39 114.7(3) . . ?
C41 C40 H40A 108.6 . . ?
C39 C40 H40A 108.6 . . ?
C41 C40 H40B 108.6 . . ?
C39 C40 H40B 108.6 . . ?
H40A C40 H40B 107.6 . . ?
C40 C41 C42 114.2(4) . . ?
C40 C41 H41A 108.7 . . ?
C42 C41 H41A 108.7 . . ?
C40 C41 H41B 108.7 . . ?
C42 C41 H41B 108.7 . . ?
H41A C41 H41B 107.6 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C7 N1 C8 108.0(2) . . ?
C7 N1 C1 126.7(2) . . ?
C8 N1 C1 125.3(2) . . ?
C7 N2 C9 108.5(2) . . ?
C7 N2 C10 125.7(2) . . ?
C9 N2 C10 125.8(2) . . ?
C28 N3 C29 108.2(2) . . ?
C28 N3 C22 127.0(2) . . ?
C29 N3 C22 124.7(2) . . ?
C28 N4 C30 108.5(2) . . ?
C28 N4 C31 125.4(3) . . ?
C30 N4 C31 126.1(2) . . ?
F3 P1 F2 89.90(13) . . ?
F3 P1 F6 89.70(17) . . ?
F2 P1 F6 90.67(14) . . ?
F3 P1 F5 91.77(16) . . ?
F2 P1 F5 90.96(14) . . ?
F6 P1 F5 177.81(14) . . ?
F3 P1 F1 179.40(13) . . ?
F2 P1 F1 90.68(12) . . ?
F6 P1 F1 90.15(14) . . ?
F5 P1 F1 88.37(13) . . ?
F3 P1 F4 90.45(12) . . ?
F2 P1 F4 179.54(13) . . ?
F6 P1 F4 89.63(14) . . ?
F5 P1 F4 88.73(13) . . ?
F1 P1 F4 88.97(12) . . ?
F12 P2 F7 90.17(14) . . ?
F12 P2 F10 88.94(18) . . ?
F7 P2 F10 90.34(17) . . ?
F12 P2 F8 92.96(18) . . ?
F7 P2 F8 91.70(16) . . ?
F10 P2 F8 177.21(15) . . ?
F12 P2 F11 178.05(16) . . ?
F7 P2 F11 91.33(14) . . ?
F10 P2 F11 89.80(15) . . ?
F8 P2 F11 88.25(15) . . ?
F12 P2 F9 91.12(14) . . ?
F7 P2 F9 178.68(14) . . ?
F10 P2 F9 89.95(17) . . ?
F8 P2 F9 87.97(16) . . ?
F11 P2 F9 87.38(13) . . ?

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
C6 C1 C2 C3 -1.3(4) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
N1 C1 C6 C5 -179.2(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
N1 C8 C9 N2 0.2(4) . . . . ?
N2 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 178.6(3) . . . . ?
C11 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 177.0(3) . . . . ?
C13 C14 C15 C16 179.0(3) . . . . ?
C14 C15 C16 C17 177.5(3) . . . . ?
C15 C16 C17 C18 178.2(3) . . . . ?
C16 C17 C18 C19 178.0(3) . . . . ?
C17 C18 C19 C20 179.1(3) . . . . ?
C18 C19 C20 C21 177.7(4) . . . . ?
C27 C22 C23 C24 1.7(4) . . . . ?
N3 C22 C23 C24 -178.4(3) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C27 1.4(5) . . . . ?
C23 C22 C27 C26 -0.7(4) . . . . ?
N3 C22 C27 C26 179.4(3) . . . . ?
C25 C26 C27 C22 -0.9(5) . . . . ?
N3 C29 C30 N4 -0.6(4) . . . . ?
N4 C31 C32 C33 175.8(3) . . . . ?
C31 C32 C33 C34 -174.9(3) . . . . ?
C32 C33 C34 C35 -70.2(4) . . . . ?
C33 C34 C35 C36 -176.3(3) . . . . ?
C34 C35 C36 C37 178.2(3) . . . . ?
C35 C36 C37 C38 -179.6(3) . . . . ?
C36 C37 C38 C39 -179.9(3) . . . . ?
C37 C38 C39 C40 -178.7(3) . . . . ?
C38 C39 C40 C41 -178.8(3) . . . . ?
C39 C40 C41 C42 -179.4(4) . . . . ?
N2 C7 N1 C8 -0.3(3) . . . . ?
N2 C7 N1 C1 178.9(2) . . . . ?
C9 C8 N1 C7 0.0(4) . . . . ?
C9 C8 N1 C1 -179.1(3) . . . . ?
C6 C1 N1 C7 -29.6(4) . . . . ?
C2 C1 N1 C7 150.9(3) . . . . ?
C6 C1 N1 C8 149.4(3) . . . . ?
C2 C1 N1 C8 -30.1(4) . . . . ?
N1 C7 N2 C9 0.4(3) . . . . ?
N1 C7 N2 C10 -178.4(3) . . . . ?
C8 C9 N2 C7 -0.4(4) . . . . ?
C8 C9 N2 C10 178.5(3) . . . . ?
C11 C10 N2 C7 110.8(3) . . . . ?
C11 C10 N2 C9 -67.9(4) . . . . ?
N4 C28 N3 C29 -0.2(3) . . . . ?
N4 C28 N3 C22 -177.5(2) . . . . ?
C30 C29 N3 C28 0.5(4) . . . . ?
C30 C29 N3 C22 177.9(3) . . . . ?
C27 C22 N3 C28 26.0(4) . . . . ?
C23 C22 N3 C28 -153.9(3) . . . . ?
C27 C22 N3 C29 -150.8(3) . . . . ?
C23 C22 N3 C29 29.3(4) . . . . ?
N3 C28 N4 C30 -0.2(3) . . . . ?
N3 C28 N4 C31 177.8(3) . . . . ?
C29 C30 N4 C28 0.5(4) . . . . ?
C29 C30 N4 C31 -177.4(3) . . . . ?
C32 C31 N4 C28 -115.8(3) . . . . ?
C32 C31 N4 C30 61.8(4) . . . . ?

_refine_diff_density_max         1.145
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_jlgld110222
_database_code_depnum_ccdc_archive 'CCDC 1830445'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-23 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         'C22 H35 N2, Br'
_chemical_formula_sum            'C22 H35 Br N2'
_chemical_formula_weight         407.43

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                   19.1863(15)
_cell_length_b                   14.2196(12)
_cell_length_c                   8.1410(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.485(2)
_cell_angle_gamma                90
_cell_volume                     2196.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4082
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.878
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_T_max  0.9119
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15505
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         28.003
_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             5300
_reflns_number_gt                3661
_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-2014/7 (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)+(0.0508P)²+0.8455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5300
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
C1 C 0.52460(12) 0.20735(17) 0.4404(3) 0.0215(5) Uani 1 1 d . . . . .
C2 C 0.58408(13) 0.15805(18) 0.5061(3) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.5869 0.0924 0.4864 0.033 Uiso 1 1 calc R U . . .
C3 C 0.64012(14) 0.2042(2) 0.6013(3) 0.0315(6) Uani 1 1 d . . . . .
C4 C 0.63420(14) 0.2996(2) 0.6298(3) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.6715 0.3317 0.6966 0.038 Uiso 1 1 calc R U . . .
C5 C 0.57471(14) 0.34865(19) 0.5625(3) 0.0314(6) Uani 1 1 d . . . . .
H5 H 0.5718 0.4142 0.5826 0.038 Uiso 1 1 calc R U . . .
C6 C 0.51917(13) 0.30334(17) 0.4659(3) 0.0260(5) Uani 1 1 d . . . . .
H6 H 0.4784 0.3372 0.4185 0.031 Uiso 1 1 calc R U . . .
C7 C 0.70596(16) 0.1507(2) 0.6701(4) 0.0517(9) Uani 1 1 d . . . . .
H7A H 0.7473 0.1832 0.6399 0.077 Uiso 1 1 calc R U . . .
H7B H 0.7035 0.0870 0.6239 0.077 Uiso 1 1 calc R U . . .
H7C H 0.7098 0.1473 0.7914 0.077 Uiso 1 1 calc R U . . .
C8 C 0.40904(13) 0.19890(17) 0.2622(3) 0.0242(5) Uani 1 1 d . . . . .
H8 H 0.3974 0.2636 0.2687 0.029 Uiso 1 1 calc R U . . .
C9 C 0.46439(13) 0.06406(17) 0.2991(3) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.4988 0.0177 0.3365 0.031 Uiso 1 1 calc R U . . .
C10 C 0.40383(14) 0.05000(17) 0.1973(3) 0.0287(6) Uani 1 1 d . . . . .
H10 H 0.3874 -0.0082 0.1491 0.034 Uiso 1 1 calc R U . . .
C11 C 0.30248(14) 0.1545(2) 0.0671(3) 0.0320(6) Uani 1 1 d . . . . .
H11A H 0.3056 0.1318 -0.0465 0.038 Uiso 1 1 calc R U . . .
H11B H 0.2947 0.2233 0.0612 0.038 Uiso 1 1 calc R U . . .
C12 C 0.24026(14) 0.10818(19) 0.1285(3) 0.0300(6) Uani 1 1 d . . . . .
H12A H 0.2491 0.0397 0.1380 0.036 Uiso 1 1 calc R U . . .
H12B H 0.1979 0.1178 0.0448 0.036 Uiso 1 1 calc R U . . .
C13 C 0.22506(13) 0.14467(19) 0.2945(3) 0.0284(6) Uani 1 1 d . . . . .
H13A H 0.2198 0.2139 0.2880 0.034 Uiso 1 1 calc R U . . .
H13B H 0.2658 0.1305 0.3804 0.034 Uiso 1 1 calc R U . . .
C14 C 0.15915(14) 0.1026(2) 0.3471(3) 0.0323(6) Uani 1 1 d . . . . .
H14A H 0.1651 0.0335 0.3568 0.039 Uiso 1 1 calc R U . . .
H14B H 0.1187 0.1150 0.2594 0.039 Uiso 1 1 calc R U . . .
C15 C 0.14224(14) 0.1412(2) 0.5117(3) 0.0327(6) Uani 1 1 d . . . . .
H15A H 0.1813 0.1250 0.6008 0.039 Uiso 1 1 calc R U . . .
H15B H 0.1395 0.2106 0.5045 0.039 Uiso 1 1 calc R U . . .
C16 C 0.07352(14) 0.1038(2) 0.5592(3) 0.0331(6) Uani 1 1 d . . . . .
H16A H 0.0761 0.0343 0.5657 0.040 Uiso 1 1 calc R U . . .
H16B H 0.0344 0.1204 0.4706 0.040 Uiso 1 1 calc R U . . .
C17 C 0.05690(14) 0.1418(2) 0.7241(3) 0.0345(6) Uani 1 1 d . . . . .
H17A H 0.0958 0.1247 0.8129 0.041 Uiso 1 1 calc R U . . .
H17B H 0.0547 0.2113 0.7180 0.041 Uiso 1 1 calc R U . . .
C18 C -0.01207(14) 0.1051(2) 0.7712(3) 0.0337(6) Uani 1 1 d . . . . .
H18A H -0.0511 0.1230 0.6833 0.040 Uiso 1 1 calc R U . . .
H18B H -0.0102 0.0356 0.7759 0.040 Uiso 1 1 calc R U . . .
C19 C -0.02793(15) 0.1422(2) 0.9369(3) 0.0359(6) Uani 1 1 d . . . . .
H19A H -0.0306 0.2116 0.9316 0.043 Uiso 1 1 calc R U . . .
H19B H 0.0115 0.1252 1.0245 0.043 Uiso 1 1 calc R U . . .
C20 C -0.09616(14) 0.1045(2) 0.9858(3) 0.0366(7) Uani 1 1 d . . . . .
H20A H -0.0935 0.0350 0.9915 0.044 Uiso 1 1 calc R U . . .
H20B H -0.1357 0.1214 0.8984 0.044 Uiso 1 1 calc R U . . .
C21 C -0.11147(17) 0.1423(2) 1.1522(4) 0.0470(8) Uani 1 1 d . . . . .
H21A H -0.0714 0.1267 1.2392 0.056 Uiso 1 1 calc R U . . .
H21B H -0.1153 0.2116 1.1456 0.056 Uiso 1 1 calc R U . . .
C22 C -0.17839(18) 0.1029(3) 1.2023(4) 0.0603(10) Uani 1 1 d . . . . .
H22A H -0.2186 0.1209 1.1198 0.090 Uiso 1 1 calc R U . . .
H22B H -0.1848 0.1281 1.3111 0.090 Uiso 1 1 calc R U . . .
H22C H -0.1751 0.0342 1.2085 0.090 Uiso 1 1 calc R U . . .
N1 N 0.46755(10) 0.15866(14) 0.3397(2) 0.0206(4) Uani 1 1 d . . . . .
N2 N 0.36976(10) 0.13493(14) 0.1751(2) 0.0250(4) Uani 1 1 d . . . . .
Br1 Br 0.36397(2) 0.43239(2) 0.17777(3) 0.03530(10) 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 C2 1.378(3) . ?
C1 C6 1.387(3) . ?
C1 N1 1.444(3) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 C7 1.510(4) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.319(3) . ?
C8 N1 1.333(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.339(4) . ?
C9 N1 1.384(3) . ?
C9 H9 0.9500 . ?
C10 N2 1.372(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.477(3) . ?
C11 C12 1.511(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.516(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.527(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.521(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.526(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.511(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(2) . . ?
C2 C1 N1 119.4(2) . . ?
C6 C1 N1 119.3(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 C7 121.1(3) . . ?
C2 C3 C7 120.2(3) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 109.4(2) . . ?
N2 C8 H8 125.3 . . ?
N1 C8 H8 125.3 . . ?
C10 C9 N1 107.2(2) . . ?
C10 C9 H9 126.4 . . ?
N1 C9 H9 126.4 . . ?
C9 C10 N2 107.6(2) . . ?
C9 C10 H10 126.2 . . ?
N2 C10 H10 126.2 . . ?
N2 C11 C12 112.6(2) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 114.3(2) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.2(2) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.6(2) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.6(2) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.6(2) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 113.7(2) . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 113.6(2) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 113.8(2) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.2(2) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 113.1(3) . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C9 107.5(2) . . ?
C8 N1 C1 125.3(2) . . ?
C9 N1 C1 127.2(2) . . ?
C8 N2 C10 108.2(2) . . ?
C8 N2 C11 124.7(2) . . ?
C10 N2 C11 126.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(4) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C2 C3 C7 -178.6(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C7 C3 C4 C5 178.1(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
N1 C9 C10 N2 -0.1(3) . . . . ?
N2 C11 C12 C13 64.8(3) . . . . ?
C11 C12 C13 C14 175.6(2) . . . . ?
C12 C13 C14 C15 -178.3(2) . . . . ?
C13 C14 C15 C16 176.2(2) . . . . ?
C14 C15 C16 C17 179.6(2) . . . . ?
C15 C16 C17 C18 179.5(2) . . . . ?
C16 C17 C18 C19 179.2(2) . . . . ?
C17 C18 C19 C20 -179.1(2) . . . . ?
C18 C19 C20 C21 -179.9(3) . . . . ?
C19 C20 C21 C22 -178.6(3) . . . . ?
N2 C8 N1 C9 -0.3(3) . . . . ?
N2 C8 N1 C1 177.0(2) . . . . ?
C10 C9 N1 C8 0.2(3) . . . . ?
C10 C9 N1 C1 -177.0(2) . . . . ?
C2 C1 N1 C8 -176.3(2) . . . . ?
C6 C1 N1 C8 2.2(3) . . . . ?
C2 C1 N1 C9 0.4(3) . . . . ?
C6 C1 N1 C9 178.9(2) . . . . ?
N1 C8 N2 C10 0.2(3) . . . . ?
N1 C8 N2 C11 -177.1(2) . . . . ?
C9 C10 N2 C8 -0.1(3) . . . . ?
C9 C10 N2 C11 177.2(2) . . . . ?
C12 C11 N2 C8 -114.9(3) . . . . ?
C12 C11 N2 C10 68.2(3) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_mdld100408_02
_database_code_depnum_ccdc_archive 'CCDC 1830446'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-05-23 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         'C33 H57 N2 O, Br'
_chemical_formula_sum            'C33 H57 Br N2 O'
_chemical_formula_weight         577.71

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'
Br Br -0.2901 2.4595 '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      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                   28.2048(7)
_cell_length_b                   14.7269(4)
_cell_length_c                   7.9430(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.506(2)
_cell_angle_gamma                90
_cell_volume                     3298.14(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    37473
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.272
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20789
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7485
_reflns_number_gt                5330
_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       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON 2003 (Spek, 2003)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0364P)²+1.5692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7485
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 1.48483(13) 0.6222(3) -0.6162(4) 0.0771(11) Uani 1 1 d . . . . .
H1A H 1.4891 0.5562 -0.6114 0.116 Uiso 1 1 calc R U . . .
H1B H 1.5148 0.6510 -0.6456 0.116 Uiso 1 1 calc R U . . .
H1C H 1.4604 0.6372 -0.7016 0.116 Uiso 1 1 calc R U . . .
C2 C 1.46970(11) 0.6566(2) -0.4458(4) 0.0621(9) Uani 1 1 d . . . . .
H2A H 1.4659 0.7234 -0.4519 0.074 Uiso 1 1 calc R U . . .
H2B H 1.4953 0.6434 -0.3615 0.074 Uiso 1 1 calc R U . . .
C3 C 1.42376(10) 0.6155(2) -0.3854(3) 0.0493(7) Uani 1 1 d . . . . .
H3A H 1.3981 0.6289 -0.4690 0.059 Uiso 1 1 calc R U . . .
H3B H 1.4274 0.5487 -0.3793 0.059 Uiso 1 1 calc R U . . .
C4 C 1.40945(9) 0.6505(2) -0.2150(3) 0.0467(7) Uani 1 1 d . . . . .
H4A H 1.4070 0.7174 -0.2207 0.056 Uiso 1 1 calc R U . . .
H4B H 1.4349 0.6355 -0.1314 0.056 Uiso 1 1 calc R U . . .
C5 C 1.36292(9) 0.61273(19) -0.1529(3) 0.0426(6) Uani 1 1 d . . . . .
H5A H 1.3372 0.6288 -0.2348 0.051 Uiso 1 1 calc R U . . .
H5B H 1.3651 0.5457 -0.1486 0.051 Uiso 1 1 calc R U . . .
C6 C 1.34996(9) 0.64768(19) 0.0198(3) 0.0418(6) Uani 1 1 d . . . . .
H6A H 1.3475 0.7147 0.0150 0.050 Uiso 1 1 calc R U . . .
H6B H 1.3759 0.6323 0.1013 0.050 Uiso 1 1 calc R U . . .
C7 C 1.30365(9) 0.60957(18) 0.0844(3) 0.0411(6) Uani 1 1 d . . . . .
H7A H 1.2778 0.6247 0.0026 0.049 Uiso 1 1 calc R U . . .
H7B H 1.3062 0.5426 0.0897 0.049 Uiso 1 1 calc R U . . .
C8 C 1.29035(9) 0.64471(18) 0.2569(3) 0.0398(6) Uani 1 1 d . . . . .
H8A H 1.3168 0.6321 0.3381 0.048 Uiso 1 1 calc R U . . .
H8B H 1.2862 0.7114 0.2507 0.048 Uiso 1 1 calc R U . . .
C9 C 1.24523(9) 0.60258(17) 0.3221(3) 0.0385(6) Uani 1 1 d . . . . .
H9A H 1.2499 0.5362 0.3320 0.046 Uiso 1 1 calc R U . . .
H9B H 1.2193 0.6130 0.2380 0.046 Uiso 1 1 calc R U . . .
C10 C 1.22984(9) 0.63897(17) 0.4915(3) 0.0371(6) Uani 1 1 d . . . . .
H10A H 1.2560 0.6305 0.5754 0.044 Uiso 1 1 calc R U . . .
H10B H 1.2236 0.7049 0.4812 0.044 Uiso 1 1 calc R U . . .
C11 C 1.18561(9) 0.59227(16) 0.5543(3) 0.0353(6) Uani 1 1 d . . . . .
H11A H 1.1599 0.5990 0.4679 0.042 Uiso 1 1 calc R U . . .
H11B H 1.1923 0.5266 0.5667 0.042 Uiso 1 1 calc R U . . .
C12 C 1.16816(9) 0.62802(16) 0.7199(3) 0.0351(6) Uani 1 1 d . . . . .
H12A H 1.1404 0.5919 0.7537 0.042 Uiso 1 1 calc R U . . .
H12B H 1.1934 0.6202 0.8076 0.042 Uiso 1 1 calc R U . . .
C13 C 1.11359(8) 0.74548(15) 0.6296(3) 0.0282(5) Uani 1 1 d . . . . .
C14 C 1.10713(8) 0.83780(15) 0.6035(3) 0.0306(5) Uani 1 1 d . . . . .
H14 H 1.1309 0.8792 0.6415 0.037 Uiso 1 1 calc R U . . .
C15 C 1.06672(8) 0.87032(15) 0.5234(3) 0.0300(5) Uani 1 1 d . . . . .
H15 H 1.0626 0.9338 0.5070 0.036 Uiso 1 1 calc R U . . .
C16 C 1.03209(8) 0.80997(15) 0.4669(3) 0.0258(5) Uani 1 1 d . . . . .
C17 C 1.03783(8) 0.71755(15) 0.4929(3) 0.0286(5) Uani 1 1 d . . . . .
H17 H 1.0140 0.6764 0.4546 0.034 Uiso 1 1 calc R U . . .
C18 C 1.07854(8) 0.68516(15) 0.5751(3) 0.0293(5) Uani 1 1 d . . . . .
H18 H 1.0824 0.6219 0.5939 0.035 Uiso 1 1 calc R U . . .
C19 C 0.95110(8) 0.80023(15) 0.3399(3) 0.0294(5) Uani 1 1 d . . . . .
H19 H 0.9439 0.7406 0.3767 0.035 Uiso 1 1 calc R U . . .
C20 C 0.98818(9) 0.92908(15) 0.2992(3) 0.0315(5) Uani 1 1 d . . . . .
H20 H 1.0116 0.9754 0.3033 0.038 Uiso 1 1 calc R U . . .
C21 C 0.94582(9) 0.93315(15) 0.2186(3) 0.0341(5) Uani 1 1 d . . . . .
H21 H 0.9339 0.9830 0.1545 0.041 Uiso 1 1 calc R U . . .
C22 C 0.87639(8) 0.82682(16) 0.1711(3) 0.0345(6) Uani 1 1 d . . . . .
H22A H 0.8712 0.7611 0.1888 0.041 Uiso 1 1 calc R U . . .
H22B H 0.8765 0.8380 0.0482 0.041 Uiso 1 1 calc R U . . .
C23 C 0.83570(9) 0.87950(16) 0.2470(3) 0.0346(6) Uani 1 1 d . . . . .
H23A H 0.8439 0.9448 0.2493 0.042 Uiso 1 1 calc R U . . .
H23B H 0.8070 0.8721 0.1736 0.042 Uiso 1 1 calc R U . . .
C24 C 0.82429(9) 0.84913(16) 0.4244(3) 0.0348(6) Uani 1 1 d . . . . .
H24A H 0.8183 0.7829 0.4232 0.042 Uiso 1 1 calc R U . . .
H24B H 0.8523 0.8603 0.4991 0.042 Uiso 1 1 calc R U . . .
C25 C 0.78185(9) 0.89636(17) 0.4978(3) 0.0408(6) Uani 1 1 d . . . . .
H25A H 0.7886 0.9622 0.5064 0.049 Uiso 1 1 calc R U . . .
H25B H 0.7541 0.8884 0.4200 0.049 Uiso 1 1 calc R U . . .
C26 C 0.76943(9) 0.86094(18) 0.6694(3) 0.0414(6) Uani 1 1 d . . . . .
H26A H 0.7963 0.8733 0.7486 0.050 Uiso 1 1 calc R U . . .
H26B H 0.7656 0.7942 0.6621 0.050 Uiso 1 1 calc R U . . .
C27 C 0.72475(10) 0.90124(18) 0.7413(3) 0.0440(6) Uani 1 1 d . . . . .
H27A H 0.7290 0.9677 0.7523 0.053 Uiso 1 1 calc R U . . .
H27B H 0.6980 0.8906 0.6605 0.053 Uiso 1 1 calc R U . . .
C28 C 0.71174(9) 0.8632(2) 0.9108(3) 0.0453(7) Uani 1 1 d . . . . .
H28A H 0.7381 0.8755 0.9922 0.054 Uiso 1 1 calc R U . . .
H28B H 0.7085 0.7964 0.9004 0.054 Uiso 1 1 calc R U . . .
C29 C 0.66635(10) 0.9009(2) 0.9815(3) 0.0496(7) Uani 1 1 d . . . . .
H29A H 0.6692 0.9677 0.9903 0.060 Uiso 1 1 calc R U . . .
H29B H 0.6397 0.8875 0.9016 0.060 Uiso 1 1 calc R U . . .
C30 C 0.65459(11) 0.8632(2) 1.1525(3) 0.0554(8) Uani 1 1 d . . . . .
H30A H 0.6513 0.7965 1.1427 0.066 Uiso 1 1 calc R U . . .
H30B H 0.6816 0.8755 1.2313 0.066 Uiso 1 1 calc R U . . .
C31 C 0.61018(11) 0.9006(2) 1.2276(4) 0.0607(9) Uani 1 1 d . . . . .
H31A H 0.6134 0.9673 1.2379 0.073 Uiso 1 1 calc R U . . .
H31B H 0.5831 0.8883 1.1491 0.073 Uiso 1 1 calc R U . . .
C32 C 0.59901(15) 0.8624(4) 1.3970(5) 0.1028(11) Uani 1 1 d . . . . .
H32A H 0.5943 0.7960 1.3852 0.123 Uiso 1 1 calc R U . . .
H32B H 0.6268 0.8719 1.4736 0.123 Uiso 1 1 calc R U . . .
C33 C 0.55621(15) 0.9019(3) 1.4777(5) 0.1028(11) Uani 1 1 d . . . . .
H33A H 0.5598 0.9679 1.4869 0.154 Uiso 1 1 calc R U . . .
H33B H 0.5530 0.8758 1.5903 0.154 Uiso 1 1 calc R U . . .
H33C H 0.5278 0.8878 1.4087 0.154 Uiso 1 1 calc R U . . .
Br1 Br 0.91606(2) 0.57858(2) 0.26528(3) 0.03776(9) Uani 1 1 d . . . . .
N1 N 0.99125(6) 0.84471(12) 0.3753(2) 0.0254(4) Uani 1 1 d . . . . .
N2 N 0.92281(6) 0.85240(12) 0.2451(2) 0.0289(4) Uani 1 1 d . . . . .
O1 O 1.15503(6) 0.72245(11) 0.71063(19) 0.0336(4) 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 C2 1.517(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O1 1.441(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O1 1.362(3) . ?
C13 C14 1.387(3) . ?
C13 C18 1.390(3) . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 N1 1.440(3) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.328(3) . ?
C19 N1 1.332(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.342(3) . ?
C20 N1 1.383(3) . ?
C20 H20 0.9500 . ?
C21 N2 1.374(3) . ?
C21 H21 0.9500 . ?
C22 N2 1.470(3) . ?
C22 C23 1.523(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.514(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.509(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.518(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.512(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.517(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.512(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.506(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.500(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.499(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 114.2(3) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 113.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 114.8(2) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 113.6(2) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 114.1(2) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 114.3(2) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 113.4(2) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 114.7(2) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 112.7(2) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 114.6(2) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O1 C12 C11 112.41(19) . . ?
O1 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
O1 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O1 C13 C14 115.0(2) . . ?
O1 C13 C18 125.6(2) . . ?
C14 C13 C18 119.4(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 N1 120.86(19) . . ?
C15 C16 N1 118.90(19) . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 119.9(2) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N2 C19 N1 109.3(2) . . ?
N2 C19 H19 125.4 . . ?
N1 C19 H19 125.4 . . ?
C21 C20 N1 107.1(2) . . ?
C21 C20 H20 126.5 . . ?
N1 C20 H20 126.5 . . ?
C20 C21 N2 107.8(2) . . ?
C20 C21 H21 126.1 . . ?
N2 C21 H21 126.1 . . ?
N2 C22 C23 112.57(19) . . ?
N2 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 113.39(19) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.21(19) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 113.2(2) . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27 114.8(2) . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C26 114.4(2) . . ?
C28 C27 H27A 108.7 . . ?
C26 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C26 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 C29 114.9(2) . . ?
C27 C28 H28A 108.5 . . ?
C29 C28 H28A 108.5 . . ?
C27 C28 H28B 108.5 . . ?
C29 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C30 C29 C28 113.9(2) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C31 C30 C29 115.2(3) . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30A 108.5 . . ?
C31 C30 H30B 108.5 . . ?
C29 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C30 114.5(3) . . ?
C32 C31 H31A 108.6 . . ?
C30 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
C30 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C33 C32 C31 115.4(4) . . ?
C33 C32 H32A 108.4 . . ?
C31 C32 H32A 108.4 . . ?
C33 C32 H32B 108.4 . . ?
C31 C32 H32B 108.4 . . ?
H32A C32 H32B 107.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C19 N1 C20 107.86(18) . . ?
C19 N1 C16 126.60(18) . . ?
C20 N1 C16 125.43(18) . . ?
C19 N2 C21 107.97(19) . . ?
C19 N2 C22 126.46(19) . . ?
C21 N2 C22 125.44(19) . . ?
C13 O1 C12 118.72(17) . . ?

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 179.8(3) . . . . ?
C2 C3 C4 C5 178.4(2) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 -177.9(2) . . . . ?
C9 C10 C11 C12 -178.3(2) . . . . ?
C10 C11 C12 O1 61.5(3) . . . . ?
O1 C13 C14 C15 -179.8(2) . . . . ?
C18 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C14 C15 C16 N1 -176.6(2) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
N1 C16 C17 C18 177.10(19) . . . . ?
O1 C13 C18 C17 -179.7(2) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
N1 C20 C21 N2 0.3(3) . . . . ?
N2 C22 C23 C24 -73.6(3) . . . . ?
C22 C23 C24 C25 -176.2(2) . . . . ?
C23 C24 C25 C26 176.4(2) . . . . ?
C24 C25 C26 C27 -175.4(2) . . . . ?
C25 C26 C27 C28 178.1(2) . . . . ?
C26 C27 C28 C29 -178.3(2) . . . . ?
C27 C28 C29 C30 -178.9(2) . . . . ?
C28 C29 C30 C31 178.9(3) . . . . ?
C29 C30 C31 C32 179.9(3) . . . . ?
C30 C31 C32 C33 177.2(3) . . . . ?
N2 C19 N1 C20 0.0(2) . . . . ?
N2 C19 N1 C16 -176.30(19) . . . . ?
C21 C20 N1 C19 -0.2(3) . . . . ?
C21 C20 N1 C16 176.2(2) . . . . ?
C17 C16 N1 C19 16.0(3) . . . . ?
C15 C16 N1 C19 -166.5(2) . . . . ?
C17 C16 N1 C20 -159.7(2) . . . . ?
C15 C16 N1 C20 17.8(3) . . . . ?
N1 C19 N2 C21 0.2(3) . . . . ?
N1 C19 N2 C22 176.3(2) . . . . ?
C20 C21 N2 C19 -0.3(3) . . . . ?
C20 C21 N2 C22 -176.5(2) . . . . ?
C23 C22 N2 C19 113.0(2) . . . . ?
C23 C22 N2 C21 -71.5(3) . . . . ?
C14 C13 O1 C12 -170.44(19) . . . . ?
C18 C13 O1 C12 10.3(3) . . . . ?
C11 C12 O1 C13 74.8(3) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.055

