# 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 2019

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1547955'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 Br N O'
_chemical_formula_sum            'C17 H18 Br N O'
_chemical_formula_weight         332.23

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                   8.529(3)
_cell_length_b                   5.781(2)
_cell_length_c                   29.757(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.78(4)
_cell_angle_gamma                90
_cell_volume                     1465.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5841
_cell_measurement_theta_min      3.0772
_cell_measurement_theta_max      28.3686

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.800
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.679
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.656
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            9237
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.550
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3534
_reflns_number_gt                2888
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0535P)²+0.7405P] 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         3534
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
Br1 Br 0.23656(3) 0.80181(4) 0.42062(2) 0.03071(10) Uani 1 1 d . . . . .
O1 O 0.52895(17) 0.3489(2) 0.71302(5) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.3277(2) 0.1359(3) 0.67052(6) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.2404(3) 0.6126(4) 0.47298(7) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.3204(3) 0.4059(4) 0.47325(8) 0.0287(5) Uani 1 1 d . . . . .
H2 H 0.374721 0.358297 0.447704 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3205(3) 0.2675(4) 0.51150(8) 0.0287(5) Uani 1 1 d . . . . .
H3 H 0.376781 0.125681 0.511971 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2402(3) 0.3318(4) 0.54901(7) 0.0237(5) Uani 1 1 d . . . . .
C5 C 0.1612(3) 0.5435(4) 0.54781(7) 0.0264(5) Uani 1 1 d . . . . .
H5 H 0.107071 0.592030 0.573328 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1603(3) 0.6847(4) 0.50993(7) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.105807 0.828053 0.509391 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2375(3) 0.1802(4) 0.59026(8) 0.0269(5) Uani 1 1 d . . . . .
H7A H 0.278477 0.025140 0.582989 0.032 Uiso 1 1 calc R U . . .
H7B H 0.127617 0.161458 0.598974 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3356(3) 0.2812(4) 0.63000(7) 0.0191(4) Uani 1 1 d . . . . .
H8A H 0.446256 0.294647 0.621733 0.023 Uiso 1 1 calc R U . . .
H8B H 0.296966 0.438368 0.636675 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3687(2) 0.2613(4) 0.71100(7) 0.0189(4) Uani 1 1 d . . . . .
H9A H 0.354938 0.158510 0.737127 0.023 Uiso 1 1 calc R U . . .
H9B H 0.295499 0.393087 0.713486 0.023 Uiso 1 1 calc R U . . .
C10 C 0.6387(2) 0.1865(3) 0.70192(7) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.7958(3) 0.2392(4) 0.71208(7) 0.0200(4) Uani 1 1 d . . . . .
H11 H 0.823028 0.380771 0.726685 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9121(2) 0.0858(4) 0.70093(7) 0.0213(4) Uani 1 1 d . . . . .
H12 H 1.018866 0.122812 0.708107 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8746(2) -0.1236(4) 0.67920(7) 0.0201(4) Uani 1 1 d . . . . .
C14 C 0.7166(2) -0.1724(3) 0.66914(7) 0.0186(4) Uani 1 1 d . . . . .
H14 H 0.689347 -0.313285 0.654305 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5973(2) -0.0202(3) 0.68025(6) 0.0168(4) Uani 1 1 d . . . . .
C16 C 0.4261(2) -0.0733(4) 0.66938(7) 0.0195(4) Uani 1 1 d . . . . .
H16A H 0.414840 -0.144017 0.639087 0.023 Uiso 1 1 calc R U . . .
H16B H 0.389116 -0.187070 0.691364 0.023 Uiso 1 1 calc R U . . .
C17 C 1.0026(3) -0.2881(4) 0.66648(8) 0.0248(5) Uani 1 1 d . . . . .
H17A H 1.050713 -0.358627 0.693737 0.037 Uiso 1 1 calc R U . . .
H17B H 1.082584 -0.203092 0.650636 0.037 Uiso 1 1 calc R U . . .
H17C H 0.957545 -0.409416 0.646796 0.037 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
Br1 C1 1.903(2) . ?
O1 C10 1.377(2) . ?
O1 C9 1.456(3) . ?
N1 C9 1.434(3) . ?
N1 C8 1.474(3) . ?
N1 C16 1.474(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.386(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.393(3) . ?
C10 C15 1.395(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 C17 1.510(3) . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.511(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C10 O1 C9 113.59(16) . . ?
C9 N1 C8 112.34(17) . . ?
C9 N1 C16 108.56(16) . . ?
C8 N1 C16 113.58(16) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 Br1 119.54(17) . . ?
C6 C1 Br1 119.14(17) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 121.7(2) . . ?
C5 C4 C7 120.2(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C4 C7 C8 112.18(17) . . ?
C4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 111.70(17) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 O1 113.61(17) . . ?
N1 C9 H9A 108.8 . . ?
O1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
O1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 117.15(18) . . ?
O1 C10 C15 122.34(18) . . ?
C11 C10 C15 120.48(18) . . ?
C12 C11 C10 120.06(19) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.97(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.00(19) . . ?
C14 C13 C17 121.4(2) . . ?
C12 C13 C17 120.55(19) . . ?
C13 C14 C15 121.95(19) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C10 C15 C14 118.53(18) . . ?
C10 C15 C16 119.57(18) . . ?
C14 C15 C16 121.90(18) . . ?
N1 C16 C15 111.94(17) . . ?
N1 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1547957'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 Br N O'
_chemical_formula_sum            'C24 H32 Br N O'
_chemical_formula_weight         430.41

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.529(4)
_cell_length_b                   8.275(2)
_cell_length_c                   21.903(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.95(2)
_cell_angle_gamma                90
_cell_volume                     4264.0(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13521
_cell_measurement_theta_min      3.1780
_cell_measurement_theta_max      36.5510

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.941
_shelx_estimated_absorpt_T_min   0.389
_shelx_estimated_absorpt_T_max   0.675
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            36838
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_max         36.896
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10122
_reflns_number_gt                5819
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXL-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10122
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_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
Br1 Br 0.50845(2) 1.39999(2) 0.34789(2) 0.02963(5) Uani 1 1 d . . . . .
O1 O 0.23881(4) 0.68035(10) 0.27338(4) 0.01712(17) Uani 1 1 d . . . . .
N1 N 0.32737(4) 0.53716(12) 0.29137(4) 0.01561(19) Uani 1 1 d . . . . .
C1 C 0.47298(5) 1.20013(15) 0.32656(5) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.50197(5) 1.05733(16) 0.33788(5) 0.0188(2) Uani 1 1 d . . . . .
H2 H 0.538281 1.058457 0.357498 0.023 Uiso 1 1 calc R U . . .
C3 C 0.47696(5) 0.91228(15) 0.32000(6) 0.0188(2) Uani 1 1 d . . . . .
H3 H 0.496431 0.813590 0.327677 0.023 Uiso 1 1 calc R U . . .
C4 C 0.42379(5) 0.90925(15) 0.29100(5) 0.0181(2) Uani 1 1 d . . . . .
C5 C 0.39534(5) 1.05532(16) 0.28209(6) 0.0209(2) Uani 1 1 d . . . . .
H5 H 0.358423 1.054421 0.263855 0.025 Uiso 1 1 calc R U . . .
C6 C 0.41943(5) 1.20226(16) 0.29912(6) 0.0204(2) Uani 1 1 d . . . . .
H6 H 0.399828 1.301094 0.292176 0.024 Uiso 1 1 calc R U . . .
C7 C 0.39761(6) 0.75340(16) 0.26869(6) 0.0242(3) Uani 1 1 d . . . . .
H7A H 0.428197 0.675140 0.259763 0.029 Uiso 1 1 calc R U . . .
H7B H 0.376092 0.773942 0.230246 0.029 Uiso 1 1 calc R U . . .
C8 C 0.35785(5) 0.68029(15) 0.31553(5) 0.0172(2) Uani 1 1 d . . . . .
H8A H 0.380195 0.648804 0.352334 0.021 Uiso 1 1 calc R U . . .
H8B H 0.329806 0.762813 0.327841 0.021 Uiso 1 1 calc R U . . .
C9 C 0.28288(5) 0.57682(14) 0.24849(5) 0.0169(2) Uani 1 1 d . . . . .
H9A H 0.265100 0.475453 0.233623 0.020 Uiso 1 1 calc R U . . .
H9B H 0.299780 0.631711 0.212967 0.020 Uiso 1 1 calc R U . . .
C10 C 0.22084(5) 0.63582(14) 0.33081(5) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.17343(5) 0.71398(14) 0.35367(5) 0.0166(2) Uani 1 1 d . . . . .
H11 H 0.154473 0.794306 0.329968 0.020 Uiso 1 1 calc R U . . .
C12 C 0.15373(5) 0.67418(14) 0.41151(5) 0.0163(2) Uani 1 1 d . . . . .
H12 H 0.121261 0.727977 0.426797 0.020 Uiso 1 1 calc R U . . .
C13 C 0.18090(5) 0.55656(14) 0.44741(5) 0.0141(2) Uani 1 1 d . . . . .
C14 C 0.22923(5) 0.48348(14) 0.42346(5) 0.0149(2) Uani 1 1 d . . . . .
H14 H 0.248955 0.405463 0.447551 0.018 Uiso 1 1 calc R U . . .
C15 C 0.24971(5) 0.52010(13) 0.36583(5) 0.0139(2) Uani 1 1 d . . . . .
C16 C 0.30229(5) 0.44040(14) 0.34070(5) 0.0156(2) Uani 1 1 d . . . . .
H16A H 0.330768 0.426281 0.374052 0.019 Uiso 1 1 calc R U . . .
H16B H 0.292206 0.331971 0.324784 0.019 Uiso 1 1 calc R U . . .
C17 C 0.16073(5) 0.50771(14) 0.51114(5) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.11042(6) 0.61046(15) 0.53199(6) 0.0209(2) Uani 1 1 d . . . . .
H18A H 0.122697 0.722864 0.537178 0.031 Uiso 1 1 calc R U . . .
H18B H 0.096621 0.568915 0.570934 0.031 Uiso 1 1 calc R U . . .
H18C H 0.079790 0.605276 0.501187 0.031 Uiso 1 1 calc R U . . .
C19 C 0.21003(6) 0.53865(16) 0.55751(6) 0.0220(3) Uani 1 1 d . . . . .
H19A H 0.243106 0.473873 0.546232 0.033 Uiso 1 1 calc R U . . .
H19B H 0.197968 0.508127 0.598536 0.033 Uiso 1 1 calc R U . . .
H19C H 0.220172 0.653499 0.557060 0.033 Uiso 1 1 calc R U . . .
C20 C 0.14727(5) 0.32391(14) 0.51529(5) 0.0153(2) Uani 1 1 d . . . . .
H20A H 0.183863 0.267243 0.509575 0.018 Uiso 1 1 d R U . . .
H20B H 0.136293 0.303803 0.558056 0.018 Uiso 1 1 d R U . . .
C21 C 0.10292(5) 0.23342(14) 0.47483(5) 0.0163(2) Uani 1 1 d . . . . .
C22 C 0.04224(6) 0.29862(17) 0.48068(6) 0.0240(3) Uani 1 1 d . . . . .
H22A H 0.032956 0.308611 0.523971 0.036 Uiso 1 1 calc R U . . .
H22B H 0.015469 0.223999 0.460701 0.036 Uiso 1 1 calc R U . . .
H22C H 0.039516 0.404906 0.461118 0.036 Uiso 1 1 calc R U . . .
C23 C 0.10298(6) 0.05776(15) 0.49819(6) 0.0232(3) Uani 1 1 d . . . . .
H23A H 0.141276 0.012341 0.494938 0.035 Uiso 1 1 calc R U . . .
H23B H 0.076265 -0.006707 0.473513 0.035 Uiso 1 1 calc R U . . .
H23C H 0.091429 0.055923 0.540964 0.035 Uiso 1 1 calc R U . . .
C24 C 0.11899(6) 0.23052(16) 0.40712(6) 0.0227(3) Uani 1 1 d . . . . .
H24A H 0.116960 0.340335 0.390472 0.034 Uiso 1 1 calc R U . . .
H24B H 0.092496 0.160484 0.384462 0.034 Uiso 1 1 calc R U . . .
H24C H 0.157754 0.188893 0.403239 0.034 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
Br1 C1 1.9072(13) . ?
O1 C10 1.3837(14) . ?
O1 C9 1.4577(15) . ?
N1 C9 1.4327(16) . ?
N1 C16 1.4757(15) . ?
N1 C8 1.4781(15) . ?
C1 C2 1.3848(18) . ?
C1 C6 1.3870(18) . ?
C2 C3 1.3902(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3940(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3939(18) . ?
C4 C7 1.5070(18) . ?
C5 C6 1.3899(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5252(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3898(17) . ?
C10 C15 1.3963(16) . ?
C11 C12 1.3956(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3992(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3978(16) . ?
C13 C17 1.5360(16) . ?
C14 C15 1.3918(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.5137(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5332(17) . ?
C17 C19 1.5501(17) . ?
C17 C20 1.5565(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5506(17) . ?
C20 H20A 0.9901 . ?
C20 H20B 0.9900 . ?
C21 C22 1.5337(18) . ?
C21 C24 1.5367(18) . ?
C21 C23 1.5410(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C10 O1 C9 114.43(9) . . ?
C9 N1 C16 107.91(9) . . ?
C9 N1 C8 113.33(10) . . ?
C16 N1 C8 111.73(9) . . ?
C2 C1 C6 121.98(12) . . ?
C2 C1 Br1 118.94(10) . . ?
C6 C1 Br1 119.07(10) . . ?
C1 C2 C3 118.77(11) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.09(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.26(11) . . ?
C5 C4 C7 120.26(12) . . ?
C3 C4 C7 121.47(12) . . ?
C6 C5 C4 121.89(12) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 117.95(12) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 C8 111.92(10) . . ?
C4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 112.11(10) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 O1 113.95(9) . . ?
N1 C9 H9A 108.8 . . ?
O1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
O1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 117.57(10) . . ?
O1 C10 C15 121.92(10) . . ?
C11 C10 C15 120.48(10) . . ?
C10 C11 C12 119.85(11) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 121.25(11) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 117.20(10) . . ?
C14 C13 C17 119.52(10) . . ?
C12 C13 C17 123.27(10) . . ?
C15 C14 C13 122.83(10) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C10 118.36(10) . . ?
C14 C15 C16 122.15(10) . . ?
C10 C15 C16 119.48(10) . . ?
N1 C16 C15 111.65(9) . . ?
N1 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C13 112.12(10) . . ?
C18 C17 C19 106.64(10) . . ?
C13 C17 C19 108.23(10) . . ?
C18 C17 C20 111.45(10) . . ?
C13 C17 C20 112.11(9) . . ?
C19 C17 C20 105.90(9) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 125.05(10) . . ?
C21 C20 H20A 106.1 . . ?
C17 C20 H20A 106.1 . . ?
C21 C20 H20B 106.0 . . ?
C17 C20 H20B 106.0 . . ?
H20A C20 H20B 106.3 . . ?
C22 C21 C24 109.30(10) . . ?
C22 C21 C23 107.44(10) . . ?
C24 C21 C23 107.87(10) . . ?
C22 C21 C20 113.64(10) . . ?
C24 C21 C20 112.65(10) . . ?
C23 C21 C20 105.60(10) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1860480'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-09-04 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.519(4)
_cell_length_b                   5.828(3)
_cell_length_c                   30.471(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.41(4)
_cell_angle_gamma                90
_cell_volume                     1510.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    939
_cell_measurement_theta_min      2.9032
_cell_measurement_theta_max      63.1089

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.582
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_reflns_number            4487
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         63.204
_diffrn_reflns_theta_full        63.204
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2389
_reflns_number_gt                1185
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0684P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   0.781
_refine_ls_restrained_S_all      0.781
_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
O1 O 0.4706(2) 0.2384(4) 0.28548(6) 0.0259(5) Uani 1 1 d . . . . .
N1 N 0.6733(3) 0.4461(4) 0.32858(7) 0.0232(7) Uani 1 1 d . . . . .
C1 C 0.7522(4) -0.0531(6) 0.52036(9) 0.0319(9) Uani 1 1 d . . . . .
C2 C 0.8323(4) -0.1194(7) 0.48399(9) 0.0366(9) Uani 1 1 d . . . . .
H2 H 0.885324 -0.262807 0.483927 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8345(4) 0.0257(6) 0.44752(10) 0.0335(9) Uani 1 1 d . . . . .
H3 H 0.889657 -0.020611 0.422815 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7577(4) 0.2363(6) 0.44659(9) 0.0306(8) Uani 1 1 d . . . . .
C5 C 0.6776(4) 0.2993(7) 0.48304(10) 0.0405(10) Uani 1 1 d . . . . .
H5 H 0.624211 0.442438 0.482969 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6738(4) 0.1579(7) 0.51959(10) 0.0404(10) Uani 1 1 d . . . . .
H6 H 0.617816 0.204453 0.544137 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7630(4) 0.3912(6) 0.40703(9) 0.0354(9) Uani 1 1 d . . . . .
H7A H 0.873236 0.406845 0.398853 0.042 Uiso 1 1 calc R U . . .
H7B H 0.724494 0.545582 0.414657 0.042 Uiso 1 1 calc R U . . .
C8 C 0.6628(4) 0.2979(6) 0.36779(9) 0.0258(8) Uani 1 1 d . . . . .
H8A H 0.698711 0.141208 0.360829 0.031 Uiso 1 1 calc R U . . .
H8B H 0.551839 0.287977 0.375546 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6315(4) 0.3239(6) 0.28832(9) 0.0240(8) Uani 1 1 d . . . . .
H9A H 0.704294 0.192760 0.285809 0.029 Uiso 1 1 calc R U . . .
H9B H 0.645961 0.427504 0.263125 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3618(4) 0.4004(6) 0.29655(9) 0.0234(8) Uani 1 1 d . . . . .
C11 C 0.2045(4) 0.3492(6) 0.28651(9) 0.0272(8) Uani 1 1 d . . . . .
H11 H 0.176327 0.209511 0.272018 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0892(4) 0.5012(6) 0.29759(9) 0.0280(8) Uani 1 1 d . . . . .
H12 H -0.017927 0.463336 0.290707 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1255(4) 0.7101(6) 0.31873(9) 0.0264(8) Uani 1 1 d . . . . .
C14 C 0.2854(4) 0.7550(6) 0.32849(9) 0.0239(8) Uani 1 1 d . . . . .
H14 H 0.313882 0.894982 0.342830 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4040(4) 0.6048(6) 0.31818(9) 0.0238(8) Uani 1 1 d . . . . .
C16 C 0.5752(4) 0.6555(6) 0.32936(9) 0.0245(8) Uani 1 1 d . . . . .
H16A H 0.612983 0.767850 0.308014 0.029 Uiso 1 1 calc R U . . .
H16B H 0.586760 0.725550 0.358972 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0013(4) 0.8715(6) 0.33122(10) 0.0337(9) Uani 1 1 d . . . . .
H17A H 0.043143 0.985364 0.352120 0.050 Uiso 1 1 calc R U . . .
H17B H -0.084249 0.785053 0.344854 0.050 Uiso 1 1 calc R U . . .
H17C H -0.045811 0.949759 0.304863 0.050 Uiso 1 1 calc R U . . .
C18 C 0.7556(4) -0.2039(7) 0.56039(11) 0.0325(9) Uani 1 1 d . . . . .
C19 C 0.7611(4) -0.3105(7) 0.58809(13) 0.0382(9) Uani 1 1 d . . . . .
H19 H 0.766130 -0.407303 0.613226 0.046 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
O1 C10 1.379(4) . ?
O1 C9 1.456(3) . ?
N1 C9 1.445(4) . ?
N1 C16 1.480(4) . ?
N1 C8 1.481(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.399(5) . ?
C1 C18 1.502(5) . ?
C2 C3 1.397(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 C7 1.509(4) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.527(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.389(4) . ?
C10 C15 1.398(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(4) . ?
C13 C17 1.499(4) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.507(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.047(4) . ?
C19 H19 0.9500 . ?

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
C10 O1 C9 113.3(2) . . ?
C9 N1 C16 108.0(2) . . ?
C9 N1 C8 112.0(2) . . ?
C16 N1 C8 114.0(2) . . ?
C2 C1 C6 119.2(3) . . ?
C2 C1 C18 119.9(3) . . ?
C6 C1 C18 120.9(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 121.4(3) . . ?
C3 C4 C7 120.5(3) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C4 C7 C8 111.8(3) . . ?
C4 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C4 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 111.5(3) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 O1 113.7(2) . . ?
N1 C9 H9A 108.8 . . ?
O1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
O1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 116.9(3) . . ?
O1 C10 C15 122.8(3) . . ?
C11 C10 C15 120.3(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 116.4(3) . . ?
C14 C13 C17 122.3(3) . . ?
C12 C13 C17 121.2(3) . . ?
C15 C14 C13 123.1(3) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C10 118.3(3) . . ?
C14 C15 C16 122.2(3) . . ?
C10 C15 C16 119.5(3) . . ?
N1 C16 C15 112.0(3) . . ?
N1 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C1 178.4(4) . . ?
C18 C19 H19 180.0 . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1835932'
loop_
_audit_author_name
_audit_author_address
'Nurbey Gulia'
;University of WrocBaw
Poland
;
_audit_update_record             
;
2018-09-04 deposited with the CCDC.	2019-07-02 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         'C29 H41 N O Si'
_chemical_formula_sum            'C29 H41 N O Si'
_chemical_formula_weight         447.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   5.837(3)
_cell_length_b                   9.730(5)
_cell_length_c                   23.888(12)
_cell_angle_alpha                80.11(3)
_cell_angle_beta                 87.86(4)
_cell_angle_gamma                89.82(4)
_cell_volume                     1335.6(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      2.9575
_cell_measurement_theta_max      34.9297

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            11351
_diffrn_reflns_av_unetI/netI     0.2257
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5496
_reflns_number_gt                2317
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0284P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5496
_refine_ls_number_parameters     298
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_restrained_S_all      0.799
_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
Si1 Si 0.57876(15) 0.52201(9) 0.65841(4) 0.0216(2) Uani 1 1 d . U . . .
O1 O -0.2841(3) 0.89188(18) 0.21165(7) 0.0207(5) Uani 1 1 d . U . . .
N1 N -0.3635(4) 1.0215(2) 0.28751(9) 0.0176(6) Uani 1 1 d . U . . .
C1 C 0.1674(5) 0.7343(3) 0.51420(12) 0.0198(7) Uani 1 1 d . U . . .
C2 C -0.0462(5) 0.6910(3) 0.50020(12) 0.0218(7) Uani 1 1 d . U . . .
H2 H -0.1091 0.6055 0.5199 0.026 Uiso 1 1 calc R U . . .
C3 C -0.1685(5) 0.7709(3) 0.45793(12) 0.0225(7) Uani 1 1 d . U . . .
H3 H -0.3122 0.7379 0.4481 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0837(5) 0.8998(3) 0.42931(12) 0.0189(7) Uani 1 1 d . U . . .
C5 C 0.1306(5) 0.9417(3) 0.44316(12) 0.0206(7) Uani 1 1 d . U . . .
H5 H 0.1934 1.0271 0.4234 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2550(5) 0.8626(3) 0.48497(12) 0.0208(7) Uani 1 1 d . U . . .
H6 H 0.4002 0.8947 0.4941 0.025 Uiso 1 1 calc R U . . .
C7 C -0.2213(5) 0.9882(3) 0.38457(12) 0.0233(7) Uani 1 1 d . U . . .
H7A H -0.1590 1.0844 0.3776 0.028 Uiso 1 1 calc R U . . .
H7B H -0.3817 0.9922 0.3991 0.028 Uiso 1 1 calc R U . . .
C8 C -0.2197(5) 0.9340(3) 0.32851(11) 0.0213(7) Uani 1 1 d . U . . .
H8A H -0.0605 0.9339 0.3127 0.026 Uiso 1 1 calc R U . . .
H8B H -0.2776 0.8369 0.3352 0.026 Uiso 1 1 calc R U . . .
C9 C -0.4570(5) 0.9478(3) 0.24684(12) 0.0243(8) Uani 1 1 d . U . . .
H9A H -0.5575 1.0115 0.2219 0.029 Uiso 1 1 calc R U . . .
H9B H -0.5531 0.8700 0.2672 0.029 Uiso 1 1 calc R U . . .
C10 C -0.1280(5) 0.9918(3) 0.18511(11) 0.0172(7) Uani 1 1 d . U . . .
C11 C 0.0018(5) 0.9615(3) 0.13772(11) 0.0154(7) Uani 1 1 d . U . . .
C12 C 0.1565(4) 1.0644(3) 0.11165(11) 0.0165(7) Uani 1 1 d . U . . .
H12 H 0.2462 1.0462 0.0797 0.020 Uiso 1 1 calc R U . . .
C13 C 0.1875(5) 1.1917(3) 0.12942(11) 0.0163(7) Uani 1 1 d . U . . .
C14 C 0.0585(5) 1.2141(3) 0.17664(11) 0.0203(7) Uani 1 1 d . U . . .
H14 H 0.0771 1.2994 0.1903 0.024 Uiso 1 1 calc R U . . .
C15 C -0.0984(5) 1.1156(3) 0.20512(12) 0.0175(7) Uani 1 1 d . U . . .
C16 C -0.2407(5) 1.1451(3) 0.25673(11) 0.0214(7) Uani 1 1 d . U . . .
H16A H -0.1382 1.1807 0.2831 0.026 Uiso 1 1 calc R U . . .
H16B H -0.3535 1.2190 0.2440 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3447(5) 1.3041(3) 0.09536(11) 0.0175(7) Uani 1 1 d . U . . .
C18 C 0.4533(5) 1.3967(3) 0.13325(12) 0.0278(8) Uani 1 1 d . U . . .
H18A H 0.3320 1.4403 0.1536 0.042 Uiso 1 1 calc R U . . .
H18B H 0.5468 1.4694 0.1096 0.042 Uiso 1 1 calc R U . . .
H18C H 0.5502 1.3396 0.1607 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5408(5) 1.2410(3) 0.06351(12) 0.0295(8) Uani 1 1 d . U . . .
H19A H 0.6254 1.1741 0.0905 0.044 Uiso 1 1 calc R U . . .
H19B H 0.6447 1.3156 0.0451 0.044 Uiso 1 1 calc R U . . .
H19C H 0.4774 1.1932 0.0346 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1983(5) 1.3966(3) 0.05167(12) 0.0304(8) Uani 1 1 d . U . . .
H20A H 0.1326 1.3396 0.0262 0.046 Uiso 1 1 calc R U . . .
H20B H 0.2947 1.4701 0.0294 0.046 Uiso 1 1 calc R U . . .
H20C H 0.0745 1.4392 0.0716 0.046 Uiso 1 1 calc R U . . .
C21 C -0.0288(5) 0.8241(3) 0.11519(11) 0.0179(7) Uani 1 1 d . U . . .
C22 C 0.0360(5) 0.7012(3) 0.16161(12) 0.0266(8) Uani 1 1 d . U . . .
H22A H 0.2006 0.7048 0.1680 0.040 Uiso 1 1 calc R U . . .
H22B H -0.0009 0.6130 0.1494 0.040 Uiso 1 1 calc R U . . .
H22C H -0.0505 0.7076 0.1970 0.040 Uiso 1 1 calc R U . . .
C23 C -0.2775(4) 0.8092(3) 0.09859(12) 0.0253(8) Uani 1 1 d . U . . .
H23A H -0.3797 0.8050 0.1323 0.038 Uiso 1 1 calc R U . . .
H23B H -0.2938 0.7234 0.0827 0.038 Uiso 1 1 calc R U . . .
H23C H -0.3180 0.8896 0.0701 0.038 Uiso 1 1 calc R U . . .
C24 C 0.1245(5) 0.8163(3) 0.06220(11) 0.0232(7) Uani 1 1 d . U . . .
H24A H 0.0818 0.8906 0.0312 0.035 Uiso 1 1 calc R U . . .
H24B H 0.1043 0.7254 0.0506 0.035 Uiso 1 1 calc R U . . .
H24C H 0.2852 0.8281 0.0709 0.035 Uiso 1 1 calc R U . . .
C25 C 0.2968(5) 0.6549(3) 0.55935(13) 0.0218(7) Uani 1 1 d . U . . .
C26 C 0.4101(5) 0.5953(3) 0.59741(13) 0.0235(8) Uani 1 1 d . U . . .
C27 C 0.7669(5) 0.6630(3) 0.67414(12) 0.0313(8) Uani 1 1 d . U . . .
H27A H 0.8757 0.6914 0.6420 0.047 Uiso 1 1 calc R U . . .
H27B H 0.8513 0.6289 0.7085 0.047 Uiso 1 1 calc R U . . .
H27C H 0.6731 0.7432 0.6803 0.047 Uiso 1 1 calc R U . . .
C28 C 0.3772(5) 0.4596(3) 0.71964(11) 0.0269(8) Uani 1 1 d . U . . .
H28A H 0.2871 0.5384 0.7289 0.040 Uiso 1 1 calc R U . . .
H28B H 0.4643 0.4185 0.7526 0.040 Uiso 1 1 calc R U . . .
H28C H 0.2739 0.3892 0.7096 0.040 Uiso 1 1 calc R U . . .
C29 C 0.7578(5) 0.3755(3) 0.64101(12) 0.0307(8) Uani 1 1 d . U . . .
H29A H 0.6600 0.3073 0.6275 0.046 Uiso 1 1 calc R U . . .
H29B H 0.8346 0.3304 0.6751 0.046 Uiso 1 1 calc R U . . .
H29C H 0.8730 0.4115 0.6113 0.046 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
Si1 C26 1.829(3) . ?
Si1 C27 1.857(3) . ?
Si1 C29 1.860(3) . ?
Si1 C28 1.861(3) . ?
O1 C10 1.389(3) . ?
O1 C9 1.453(3) . ?
N1 C9 1.427(3) . ?
N1 C8 1.469(3) . ?
N1 C16 1.471(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.408(4) . ?
C1 C25 1.450(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 C7 1.507(4) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.384(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.398(3) . ?
C11 C21 1.538(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 C17 1.531(3) . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.528(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.535(4) . ?
C17 C18 1.536(4) . ?
C17 C20 1.539(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.533(3) . ?
C21 C24 1.535(3) . ?
C21 C22 1.541(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.209(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C26 Si1 C27 107.54(14) . . ?
C26 Si1 C29 110.08(14) . . ?
C27 Si1 C29 109.59(14) . . ?
C26 Si1 C28 108.23(14) . . ?
C27 Si1 C28 110.92(13) . . ?
C29 Si1 C28 110.44(14) . . ?
C10 O1 C9 113.10(19) . . ?
C9 N1 C8 113.3(2) . . ?
C9 N1 C16 108.4(2) . . ?
C8 N1 C16 112.5(2) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 C25 122.0(3) . . ?
C6 C1 C25 119.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C7 121.5(3) . . ?
C3 C4 C7 120.7(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C4 C7 C8 113.4(2) . . ?
C4 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C4 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C7 110.8(2) . . ?
N1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 O1 113.6(2) . . ?
N1 C9 H9A 108.9 . . ?
O1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
O1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 O1 121.0(2) . . ?
C15 C10 C11 121.3(2) . . ?
O1 C10 C11 117.7(2) . . ?
C12 C11 C10 116.4(2) . . ?
C12 C11 C21 121.8(2) . . ?
C10 C11 C21 121.8(2) . . ?
C13 C12 C11 124.2(3) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C14 C13 C12 116.6(2) . . ?
C14 C13 C17 122.3(2) . . ?
C12 C13 C17 120.9(2) . . ?
C13 C14 C15 122.3(2) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C14 119.1(3) . . ?
C10 C15 C16 120.1(2) . . ?
C14 C15 C16 120.8(2) . . ?
N1 C16 C15 113.2(2) . . ?
N1 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C13 C17 C19 112.1(2) . . ?
C13 C17 C18 112.3(2) . . ?
C19 C17 C18 107.5(2) . . ?
C13 C17 C20 107.7(2) . . ?
C19 C17 C20 108.7(2) . . ?
C18 C17 C20 108.5(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C24 107.1(2) . . ?
C23 C21 C11 110.1(2) . . ?
C24 C21 C11 112.6(2) . . ?
C23 C21 C22 110.4(2) . . ?
C24 C21 C22 107.6(2) . . ?
C11 C21 C22 109.1(2) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C1 176.5(3) . . ?
C25 C26 Si1 173.8(3) . . ?
Si1 C27 H27A 109.5 . . ?
Si1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
Si1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Si1 C28 H28A 109.5 . . ?
Si1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
Si1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Si1 C29 H29A 109.5 . . ?
Si1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
Si1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1860482'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2019-07-02 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 H25 N O'
_chemical_formula_sum            'C22 H25 N O'
_chemical_formula_weight         319.43

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'
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                   18.203(4)
_cell_length_b                   8.747(3)
_cell_length_c                   11.179(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                90
_cell_volume                     1758.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5338
_cell_measurement_theta_min      2.9644
_cell_measurement_theta_max      30.9574

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            13304
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.970
_diffrn_reflns_theta_max         31.027
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5117
_reflns_number_gt                4032
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0437P)²+0.6056P] 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         5117
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.23365(4) 0.40328(10) 0.62614(7) 0.01995(19) Uani 1 1 d . . . . .
N1 N 0.33326(5) 0.37756(12) 0.79458(9) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.61891(6) 0.21780(14) 0.53022(10) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.63097(6) 0.32566(14) 0.62266(11) 0.0200(2) Uani 1 1 d . . . . .
H2 H 0.6803 0.3553 0.6547 0.024 Uiso 1 1 calc R U . . .
C3 C 0.57135(6) 0.39024(14) 0.66828(11) 0.0196(2) Uani 1 1 d . . . . .
H3 H 0.5805 0.4635 0.7315 0.024 Uiso 1 1 calc R U . . .
C4 C 0.49831(6) 0.34974(14) 0.62318(10) 0.0176(2) Uani 1 1 d . . . . .
C5 C 0.48673(6) 0.23912(16) 0.53260(11) 0.0221(3) Uani 1 1 d . . . . .
H5 H 0.4375 0.2076 0.5020 0.027 Uiso 1 1 calc R U . . .
C6 C 0.54583(7) 0.17438(16) 0.48645(11) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.5366 0.0996 0.4243 0.027 Uiso 1 1 calc R U . . .
C7 C 0.43337(6) 0.42283(14) 0.67085(11) 0.0202(2) Uani 1 1 d . . . . .
H7A H 0.4022 0.4778 0.6041 0.024 Uiso 1 1 calc R U . . .
H7B H 0.4523 0.4986 0.7339 0.024 Uiso 1 1 calc R U . . .
C8 C 0.38565(6) 0.30522(14) 0.72450(10) 0.0171(2) Uani 1 1 d . . . . .
H8A H 0.3576 0.2441 0.6582 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4184 0.2347 0.7777 0.021 Uiso 1 1 calc R U . . .
C9 C 0.28153(6) 0.47828(14) 0.72554(11) 0.0198(2) Uani 1 1 d . . . . .
H9A H 0.3094 0.5612 0.6921 0.024 Uiso 1 1 calc R U . . .
H9B H 0.2500 0.5257 0.7801 0.024 Uiso 1 1 calc R U . . .
C10 C 0.19935(6) 0.27505(14) 0.66295(10) 0.0171(2) Uani 1 1 d . . . . .
C11 C 0.13932(6) 0.21509(14) 0.58572(10) 0.0184(2) Uani 1 1 d . . . . .
H11 H 0.1236 0.2612 0.5091 0.022 Uiso 1 1 calc R U . . .
C12 C 0.10217(6) 0.08791(14) 0.62021(10) 0.0171(2) Uani 1 1 d . . . . .
H12 H 0.0614 0.0476 0.5661 0.021 Uiso 1 1 calc R U . . .
C13 C 0.12313(6) 0.01752(13) 0.73249(10) 0.0146(2) Uani 1 1 d . . . . .
C14 C 0.18521(6) 0.07763(13) 0.80664(10) 0.0150(2) Uani 1 1 d . . . . .
H14 H 0.2016 0.0302 0.8825 0.018 Uiso 1 1 calc R U . . .
C15 C 0.22406(6) 0.20416(13) 0.77400(10) 0.0154(2) Uani 1 1 d . . . . .
C16 C 0.29141(6) 0.26607(14) 0.85589(10) 0.0179(2) Uani 1 1 d . . . . .
H16A H 0.2751 0.3154 0.9270 0.021 Uiso 1 1 calc R U . . .
H16B H 0.3246 0.1800 0.8855 0.021 Uiso 1 1 calc R U . . .
C17 C 0.08256(6) -0.12129(14) 0.77405(10) 0.0168(2) Uani 1 1 d . . . . .
C18 C 0.13327(8) -0.26141(16) 0.77812(15) 0.0316(3) Uani 1 1 d . . . . .
H18A H 0.1449 -0.2819 0.6969 0.047 Uiso 1 1 calc R U . . .
H18B H 0.1080 -0.3502 0.8064 0.047 Uiso 1 1 calc R U . . .
H18C H 0.1794 -0.2418 0.8337 0.047 Uiso 1 1 calc R U . . .
C19 C 0.01022(7) -0.15615(16) 0.68919(11) 0.0229(3) Uani 1 1 d . . . . .
H19A H -0.0218 -0.0656 0.6822 0.034 Uiso 1 1 calc R U . . .
H19B H -0.0154 -0.2414 0.7220 0.034 Uiso 1 1 calc R U . . .
H19C H 0.0216 -0.1838 0.6091 0.034 Uiso 1 1 calc R U . . .
C20 C 0.06241(8) -0.09171(18) 0.90051(12) 0.0309(3) Uani 1 1 d . . . . .
H20A H 0.1080 -0.0747 0.9582 0.046 Uiso 1 1 calc R U . . .
H20B H 0.0359 -0.1805 0.9261 0.046 Uiso 1 1 calc R U . . .
H20C H 0.0306 -0.0011 0.8980 0.046 Uiso 1 1 calc R U . . .
C21 C 0.67974(7) 0.15122(15) 0.48002(11) 0.0209(2) Uani 1 1 d . . . . .
C22 C 0.72953(7) 0.09722(17) 0.43703(12) 0.0267(3) Uani 1 1 d . . . . .
H22 H 0.7694 0.0540 0.4026 0.032 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
O1 C10 1.3770(14) . ?
O1 C9 1.4586(15) . ?
N1 C9 1.4267(16) . ?
N1 C8 1.4674(15) . ?
N1 C16 1.4702(15) . ?
C1 C2 1.3916(17) . ?
C1 C6 1.3976(17) . ?
C1 C21 1.4391(17) . ?
C2 C3 1.3881(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3934(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3930(18) . ?
C4 C7 1.5111(16) . ?
C5 C6 1.3837(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5272(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3874(17) . ?
C10 C15 1.3987(16) . ?
C11 C12 1.3869(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3975(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3974(16) . ?
C13 C17 1.5300(16) . ?
C14 C15 1.3919(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.5131(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5308(18) . ?
C17 C19 1.5308(17) . ?
C17 C20 1.5360(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.1872(18) . ?
C22 H22 0.9500 . ?

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
C10 O1 C9 112.58(9) . . ?
C9 N1 C8 113.99(9) . . ?
C9 N1 C16 108.40(9) . . ?
C8 N1 C16 112.87(10) . . ?
C2 C1 C6 118.51(11) . . ?
C2 C1 C21 121.39(11) . . ?
C6 C1 C21 120.10(11) . . ?
C3 C2 C1 120.38(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.33(11) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.98(11) . . ?
C5 C4 C7 120.73(11) . . ?
C3 C4 C7 121.29(11) . . ?
C6 C5 C4 121.04(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.73(12) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C4 C7 C8 112.11(10) . . ?
C4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 112.00(10) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 O1 113.70(10) . . ?
N1 C9 H9A 108.8 . . ?
O1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
O1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 118.15(10) . . ?
O1 C10 C15 121.84(10) . . ?
C11 C10 C15 120.00(11) . . ?
C12 C11 C10 120.08(10) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.70(11) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 116.83(11) . . ?
C14 C13 C17 120.17(10) . . ?
C12 C13 C17 122.98(10) . . ?
C15 C14 C13 122.74(10) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C10 118.55(10) . . ?
C14 C15 C16 121.54(10) . . ?
C10 C15 C16 119.91(10) . . ?
N1 C16 C15 112.64(9) . . ?
N1 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
N1 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C13 C17 C18 109.11(10) . . ?
C13 C17 C19 112.29(10) . . ?
C18 C17 C19 108.45(10) . . ?
C13 C17 C20 109.90(10) . . ?
C18 C17 C20 109.61(11) . . ?
C19 C17 C20 107.44(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C1 179.04(14) . . ?
C21 C22 H22 180.0 . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1547956'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2019-07-02 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         'C20 H24 Br N O'
_chemical_formula_sum            'C20 H24 Br N O'
_chemical_formula_weight         374.31

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                   17.652(5)
_cell_length_b                   8.838(3)
_cell_length_c                   11.184(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.65(3)
_cell_angle_gamma                90
_cell_volume                     1736.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7795
_cell_measurement_theta_min      2.8038
_cell_measurement_theta_max      30.9929

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.372
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            18215
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         31.062
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5373
_reflns_number_gt                3665
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0486P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5373
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_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
Br1 Br 0.28594(2) 0.61228(2) 0.55910(2) 0.02452(7) Uani 1 1 d . . . . .
O1 O 0.75971(7) 0.89956(16) 0.37594(12) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.66237(9) 0.87170(18) 0.20998(15) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.36952(11) 0.7035(2) 0.49132(17) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.44301(11) 0.6614(2) 0.53177(19) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.4518 0.5863 0.5923 0.027 Uiso 1 1 calc R U . . .
C3 C 0.50389(11) 0.7295(2) 0.48347(18) 0.0217(4) Uani 1 1 d . . . . .
H3 H 0.5543 0.7006 0.5116 0.026 Uiso 1 1 calc R U . . .
C4 C 0.49234(10) 0.8395(2) 0.39448(17) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.41784(11) 0.8781(2) 0.35422(17) 0.0185(4) Uani 1 1 d . . . . .
H5 H 0.4089 0.9519 0.2927 0.022 Uiso 1 1 calc R U . . .
C6 C 0.35604(11) 0.8111(2) 0.40196(18) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.3055 0.8389 0.3736 0.025 Uiso 1 1 calc R U . . .
C7 C 0.55928(11) 0.9135(2) 0.34255(19) 0.0200(4) Uani 1 1 d . . . . .
H7A H 0.5911 0.9662 0.4075 0.024 Uiso 1 1 calc R U . . .
H7B H 0.5402 0.9901 0.2824 0.024 Uiso 1 1 calc R U . . .
C8 C 0.60818(11) 0.7986(2) 0.28316(18) 0.0182(4) Uani 1 1 d . . . . .
H8A H 0.6366 0.7364 0.3461 0.022 Uiso 1 1 calc R U . . .
H8B H 0.5747 0.7302 0.2316 0.022 Uiso 1 1 calc R U . . .
C9 C 0.71391(11) 0.9727(2) 0.27685(18) 0.0202(4) Uani 1 1 d . . . . .
H9A H 0.6844 1.0559 0.3092 0.024 Uiso 1 1 calc R U . . .
H9B H 0.7483 1.0180 0.2218 0.024 Uiso 1 1 calc R U . . .
C10 C 0.79563(10) 0.7704(2) 0.34061(18) 0.0176(4) Uani 1 1 d . . . . .
C11 C 0.85386(11) 0.7105(2) 0.41859(18) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.8673 0.7568 0.4944 0.023 Uiso 1 1 calc R U . . .
C12 C 0.89246(11) 0.5828(2) 0.38550(17) 0.0185(4) Uani 1 1 d . . . . .
H12 H 0.9317 0.5418 0.4403 0.022 Uiso 1 1 calc R U . . .
C13 C 0.87549(10) 0.5127(2) 0.27418(17) 0.0153(4) Uani 1 1 d . . . . .
C14 C 0.81474(10) 0.5731(2) 0.19935(17) 0.0156(4) Uani 1 1 d . . . . .
H14 H 0.8007 0.5261 0.1240 0.019 Uiso 1 1 calc R U . . .
C15 C 0.77409(10) 0.6992(2) 0.23094(17) 0.0156(4) Uani 1 1 d . . . . .
C16 C 0.70755(11) 0.7610(2) 0.14827(18) 0.0182(4) Uani 1 1 d . . . . .
H16A H 0.7272 0.8100 0.0780 0.022 Uiso 1 1 calc R U . . .
H16B H 0.6743 0.6761 0.1185 0.022 Uiso 1 1 calc R U . . .
C17 C 0.91968(11) 0.3761(2) 0.23394(18) 0.0188(4) Uani 1 1 d . . . . .
C18 C 0.99162(11) 0.3444(3) 0.3172(2) 0.0268(5) Uani 1 1 d . . . . .
H18A H 1.0238 0.4350 0.3231 0.040 Uiso 1 1 calc R U . . .
H18B H 1.0196 0.2605 0.2848 0.040 Uiso 1 1 calc R U . . .
H18C H 0.9777 0.3174 0.3971 0.040 Uiso 1 1 calc R U . . .
C19 C 0.86884(13) 0.2350(3) 0.2308(3) 0.0381(6) Uani 1 1 d . . . . .
H19A H 0.8535 0.2158 0.3114 0.057 Uiso 1 1 calc R U . . .
H19B H 0.8971 0.1476 0.2046 0.057 Uiso 1 1 calc R U . . .
H19C H 0.8234 0.2516 0.1746 0.057 Uiso 1 1 calc R U . . .
C20 C 0.94463(15) 0.4062(3) 0.1083(2) 0.0361(6) Uani 1 1 d . . . . .
H20A H 0.8996 0.4221 0.0512 0.054 Uiso 1 1 calc R U . . .
H20B H 0.9734 0.3190 0.0828 0.054 Uiso 1 1 calc R U . . .
H20C H 0.9769 0.4966 0.1108 0.054 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
Br1 C1 1.903(2) . ?
O1 C10 1.383(2) . ?
O1 C9 1.457(2) . ?
N1 C9 1.432(3) . ?
N1 C8 1.468(2) . ?
N1 C16 1.476(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 C7 1.515(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.526(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.386(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 C17 1.529(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.525(3) . ?
C17 C19 1.534(3) . ?
C17 C20 1.536(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C10 O1 C9 112.64(15) . . ?
C9 N1 C8 113.48(16) . . ?
C9 N1 C16 108.24(15) . . ?
C8 N1 C16 112.37(15) . . ?
C2 C1 C6 120.70(18) . . ?
C2 C1 Br1 119.69(16) . . ?
C6 C1 Br1 119.61(14) . . ?
C1 C2 C3 119.61(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.14(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.06(18) . . ?
C5 C4 C7 121.23(18) . . ?
C3 C4 C7 120.70(18) . . ?
C4 C5 C6 121.54(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.93(18) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C4 C7 C8 112.07(16) . . ?
C4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 112.17(16) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 O1 113.38(16) . . ?
N1 C9 H9A 108.9 . . ?
O1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
O1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 117.90(17) . . ?
O1 C10 C15 121.99(17) . . ?
C11 C10 C15 120.10(18) . . ?
C10 C11 C12 119.73(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 122.07(18) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 116.63(17) . . ?
C12 C13 C17 122.81(17) . . ?
C14 C13 C17 120.56(17) . . ?
C15 C14 C13 122.57(18) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C14 C15 C10 118.78(17) . . ?
C14 C15 C16 121.33(17) . . ?
C10 C15 C16 119.89(17) . . ?
N1 C16 C15 111.95(16) . . ?
N1 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C13 112.56(17) . . ?
C18 C17 C19 108.35(18) . . ?
C13 C17 C19 109.50(17) . . ?
C18 C17 C20 107.07(18) . . ?
C13 C17 C20 109.44(17) . . ?
C19 C17 C20 109.9(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.641
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1835916'
loop_
_audit_author_name
_audit_author_address
'Nurbey Gulia'
;University of WrocBaw
Poland
;
_audit_update_record             
;
2018-04-13 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
6,8-di-tert-butyl-3-(4-ethynylphenethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '1.95(C26 H33 N O), 0.05(C24 H32 N O I)'
_chemical_formula_sum            'C51.90 H65.95 I0.05 N2 O2'
_chemical_formula_weight         756.16

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'
I I -0.4742 1.8119 '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                   19.608(3)
_cell_length_b                   10.754(2)
_cell_length_c                   21.654(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.84(3)
_cell_angle_gamma                90
_cell_volume                     4392.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23271
_cell_measurement_theta_min      2.9275
_cell_measurement_theta_max      32.4997

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            68555
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         32.573
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             15649
_reflns_number_gt                9899
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0695P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15649
_refine_ls_number_parameters     521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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
O1 O 0.70026(3) 0.34868(6) 0.39635(3) 0.01862(14) Uani 1 1 d . . . . .
N1 N 0.59989(4) 0.48799(7) 0.37863(4) 0.01670(16) Uani 1 1 d . . . . .
C1 C 0.37719(5) 0.45344(9) 0.09418(5) 0.01744(18) Uani 1 1 d . . . . .
C2 C 0.36175(5) 0.55389(9) 0.12914(5) 0.01997(19) Uani 1 1 d . . . . .
H2 H 0.318679 0.598504 0.113381 0.024 Uiso 1 1 calc R U . . .
C3 C 0.40902(5) 0.58853(9) 0.18665(5) 0.01918(19) Uani 1 1 d . . . . .
H3 H 0.397744 0.657023 0.209770 0.023 Uiso 1 1 calc R U . . .
C4 C 0.47288(5) 0.52523(9) 0.21151(5) 0.01688(18) Uani 1 1 d . . . . .
C5 C 0.48862(5) 0.42699(9) 0.17556(5) 0.01809(18) Uani 1 1 d . . . . .
H5 H 0.532239 0.383753 0.190816 0.022 Uiso 1 1 calc R U . . .
C6 C 0.44171(5) 0.39149(9) 0.11802(5) 0.01851(18) Uani 1 1 d . . . . .
H6 H 0.453529 0.324185 0.094464 0.022 Uiso 1 1 calc R U . . .
C7 C 0.52191(5) 0.56440(9) 0.27548(5) 0.01838(18) Uani 1 1 d . . . . .
H7A H 0.492749 0.589080 0.304251 0.022 Uiso 1 1 calc R U . . .
H7B H 0.548864 0.638560 0.268640 0.022 Uiso 1 1 calc R U . . .
C8 C 0.57449(5) 0.46461(9) 0.30910(5) 0.01701(18) Uani 1 1 d . . . . .
H8A H 0.551291 0.382104 0.301661 0.020 Uiso 1 1 calc R U . . .
H8B H 0.615373 0.463391 0.290554 0.020 Uiso 1 1 calc R U . . .
C9 C 0.63599(5) 0.38311(9) 0.41340(5) 0.01853(18) Uani 1 1 d . . . . .
H9A H 0.603309 0.311082 0.405502 0.022 Uiso 1 1 calc R U . . .
H9B H 0.648351 0.401991 0.459885 0.022 Uiso 1 1 calc R U . . .
C10 C 0.74660(5) 0.44647(9) 0.39806(4) 0.01583(17) Uani 1 1 d . . . . .
C11 C 0.81764(5) 0.41941(9) 0.40045(4) 0.01629(17) Uani 1 1 d . . . . .
C12 C 0.86229(5) 0.52102(9) 0.40111(5) 0.01737(18) Uani 1 1 d . . . . .
H12 H 0.910235 0.504967 0.402154 0.021 Uiso 1 1 calc R U . . .
C13 C 0.84051(5) 0.64468(9) 0.40033(4) 0.01670(18) Uani 1 1 d . . . . .
C14 C 0.76983(5) 0.66614(9) 0.39810(5) 0.01682(18) Uani 1 1 d . . . . .
H14 H 0.753418 0.749359 0.397551 0.020 Uiso 1 1 calc R U . . .
C15 C 0.72271(5) 0.56901(9) 0.39666(4) 0.01577(17) Uani 1 1 d . . . . .
C16 C 0.64663(5) 0.59693(9) 0.39539(5) 0.01815(18) Uani 1 1 d . . . . .
H16A H 0.645373 0.627817 0.438138 0.022 Uiso 1 1 calc R U . . .
H16B H 0.628375 0.663857 0.363816 0.022 Uiso 1 1 calc R U . . .
C17 C 0.89064(5) 0.75522(9) 0.40244(5) 0.01969(19) Uani 1 1 d . . . . .
C18 C 0.86143(6) 0.83801(11) 0.34355(6) 0.0309(3) Uani 1 1 d . . . . .
H18A H 0.857957 0.789717 0.304438 0.046 Uiso 1 1 calc R U . . .
H18B H 0.893330 0.908774 0.345059 0.046 Uiso 1 1 calc R U . . .
H18C H 0.814309 0.868489 0.343507 0.046 Uiso 1 1 calc R U . . .
C19 C 0.89596(6) 0.83082(10) 0.46388(6) 0.0287(2) Uani 1 1 d . . . . .
H19A H 0.848785 0.860931 0.463872 0.043 Uiso 1 1 calc R U . . .
H19B H 0.927701 0.901829 0.465388 0.043 Uiso 1 1 calc R U . . .
H19C H 0.914787 0.777877 0.501512 0.043 Uiso 1 1 calc R U . . .
C20 C 0.96527(5) 0.71375(10) 0.40251(6) 0.0257(2) Uani 1 1 d . . . . .
H20A H 0.984125 0.657327 0.438688 0.039 Uiso 1 1 calc R U . . .
H20B H 0.996143 0.786713 0.406686 0.039 Uiso 1 1 calc R U . . .
H20C H 0.963373 0.670635 0.362206 0.039 Uiso 1 1 calc R U . . .
C21 C 0.84564(5) 0.28543(9) 0.40423(5) 0.01933(19) Uani 1 1 d . . . . .
C22 C 0.80663(6) 0.21206(10) 0.34421(5) 0.0249(2) Uani 1 1 d . . . . .
H22A H 0.755388 0.217398 0.338525 0.037 Uiso 1 1 calc R U . . .
H22B H 0.821484 0.124780 0.349292 0.037 Uiso 1 1 calc R U . . .
H22C H 0.818101 0.247125 0.306490 0.037 Uiso 1 1 calc R U . . .
C23 C 0.92505(6) 0.28045(10) 0.40791(6) 0.0260(2) Uani 1 1 d . . . . .
H23A H 0.932733 0.316710 0.368829 0.039 Uiso 1 1 calc R U . . .
H23B H 0.941073 0.193759 0.411883 0.039 Uiso 1 1 calc R U . . .
H23C H 0.951952 0.327692 0.445355 0.039 Uiso 1 1 calc R U . . .
C24 C 0.83636(6) 0.22152(10) 0.46503(5) 0.0240(2) Uani 1 1 d . . . . .
H24A H 0.862586 0.267964 0.503042 0.036 Uiso 1 1 calc R U . . .
H24B H 0.854637 0.136337 0.467306 0.036 Uiso 1 1 calc R U . . .
H24C H 0.785941 0.219566 0.463450 0.036 Uiso 1 1 calc R U . . .
C25 C 0.32792(5) 0.41434(9) 0.03463(5) 0.01995(19) Uani 1 1 d . . . . .
C26 C 0.28791(6) 0.37993(10) -0.01358(5) 0.0247(2) Uani 1 1 d . . . . .
H26 H 0.255729 0.352260 -0.052356 0.030 Uiso 1 1 calc R U . . .
O2 O 0.29093(4) 0.41781(6) 0.32073(3) 0.02139(15) Uani 1 1 d . . . . .
N2 N 0.37671(5) 0.28437(8) 0.29220(4) 0.02227(18) Uani 1 1 d . . . . .
C31 C 0.59100(5) 0.24353(10) 0.58126(5) 0.0224(2) Uani 1 1 d . . . . .
C32 C 0.57825(6) 0.14813(10) 0.53573(5) 0.0242(2) Uani 1 1 d . . . . .
H32 H 0.609149 0.078449 0.541649 0.029 Uiso 1 1 calc R U . . .
C33 C 0.52071(5) 0.15498(10) 0.48204(5) 0.0228(2) Uani 1 1 d . . . . .
H33 H 0.512879 0.089967 0.451194 0.027 Uiso 1 1 calc R U . . .
C34 C 0.47379(5) 0.25576(9) 0.47223(5) 0.02053(19) Uani 1 1 d . . . . .
C35 C 0.48823(6) 0.35177(9) 0.51706(5) 0.0217(2) Uani 1 1 d . . . . .
H35 H 0.457745 0.422040 0.510819 0.026 Uiso 1 1 calc R U . . .
C36 C 0.54613(6) 0.34678(9) 0.57055(5) 0.0229(2) Uani 1 1 d . . . . .
H36 H 0.555401 0.413983 0.600149 0.027 Uiso 1 1 calc R U . . .
C37 C 0.41020(6) 0.26027(10) 0.41488(5) 0.0238(2) Uani 1 1 d . . . . .
H37A H 0.378390 0.328404 0.420322 0.029 Uiso 1 1 calc R U . . .
H37B H 0.383696 0.181083 0.411544 0.029 Uiso 1 1 calc R U . . .
C38 C 0.43266(5) 0.28151(10) 0.35288(5) 0.0217(2) Uani 1 1 d . . . . .
H38A H 0.458641 0.361396 0.357246 0.026 Uiso 1 1 calc R U . . .
H38B H 0.466542 0.215064 0.349841 0.026 Uiso 1 1 calc R U . . .
C39 C 0.33712(6) 0.39646(10) 0.27959(5) 0.0243(2) Uani 1 1 d . . . . .
H39A H 0.307913 0.395436 0.234391 0.029 Uiso 1 1 calc R U . . .
H39B H 0.370569 0.467064 0.284488 0.029 Uiso 1 1 calc R U . . .
C40 C 0.24742(5) 0.31824(9) 0.32354(5) 0.01769(18) Uani 1 1 d . . . . .
C41 C 0.18795(5) 0.33974(9) 0.34672(4) 0.01705(18) Uani 1 1 d . . . . .
C42 C 0.14368(5) 0.23826(9) 0.34706(5) 0.01801(18) Uani 1 1 d . . . . .
H42 H 0.103097 0.250673 0.362261 0.022 Uiso 1 1 calc R U . . .
C43 C 0.15584(5) 0.11934(9) 0.32623(5) 0.01802(18) Uani 1 1 d . . . . .
C44 C 0.21670(5) 0.10248(9) 0.30576(5) 0.01997(19) Uani 1 1 d . . . . .
H44 H 0.226963 0.022236 0.292278 0.024 Uiso 1 1 calc R U . . .
C45 C 0.26278(5) 0.20020(9) 0.30457(5) 0.01871(19) Uani 1 1 d . . . . .
C46 C 0.32814(5) 0.17790(10) 0.28108(5) 0.0233(2) Uani 1 1 d . . . . .
H46A H 0.353723 0.104155 0.303279 0.028 Uiso 1 1 calc R U . . .
H46B H 0.312953 0.159418 0.234533 0.028 Uiso 1 1 calc R U . . .
C47 C 0.10667(5) 0.00917(9) 0.32714(5) 0.0214(2) Uani 1 1 d . . . . .
C48 C 0.14594(7) -0.08559(11) 0.37742(6) 0.0325(3) Uani 1 1 d . . . . .
H48A H 0.188932 -0.113514 0.366765 0.049 Uiso 1 1 calc R U . . .
H48B H 0.115038 -0.157120 0.377644 0.049 Uiso 1 1 calc R U . . .
H48C H 0.158891 -0.046598 0.419941 0.049 Uiso 1 1 calc R U . . .
C49 C 0.08536(7) -0.05347(13) 0.26128(6) 0.0382(3) Uani 1 1 d . . . . .
H49A H 0.060347 0.006513 0.228904 0.057 Uiso 1 1 calc R U . . .
H49B H 0.054142 -0.124133 0.262337 0.057 Uiso 1 1 calc R U . . .
H49C H 0.127929 -0.082933 0.250378 0.057 Uiso 1 1 calc R U . . .
C50 C 0.03934(6) 0.04872(12) 0.34440(7) 0.0374(3) Uani 1 1 d . . . . .
H50A H 0.052001 0.085063 0.387536 0.056 Uiso 1 1 calc R U . . .
H50B H 0.008958 -0.024020 0.343416 0.056 Uiso 1 1 calc R U . . .
H50C H 0.013862 0.110494 0.313314 0.056 Uiso 1 1 calc R U . . .
C51 C 0.17169(5) 0.46931(9) 0.36893(5) 0.02027(19) Uani 1 1 d . . . . .
C52 C 0.23457(6) 0.51740(10) 0.42308(5) 0.0264(2) Uani 1 1 d . . . . .
H52A H 0.243881 0.459614 0.459423 0.040 Uiso 1 1 calc R U . . .
H52B H 0.223060 0.599612 0.436995 0.040 Uiso 1 1 calc R U . . .
H52C H 0.276753 0.523576 0.407275 0.040 Uiso 1 1 calc R U . . .
C53 C 0.10679(6) 0.46769(11) 0.39582(6) 0.0293(2) Uani 1 1 d . . . . .
H53A H 0.065175 0.439094 0.362465 0.044 Uiso 1 1 calc R U . . .
H53B H 0.098118 0.551730 0.409453 0.044 Uiso 1 1 calc R U . . .
H53C H 0.115713 0.411206 0.432677 0.044 Uiso 1 1 calc R U . . .
C54 C 0.15548(6) 0.55888(10) 0.31144(6) 0.0293(2) Uani 1 1 d . . . . .
H54A H 0.196750 0.564095 0.294277 0.044 Uiso 1 1 calc R U . . .
H54B H 0.144777 0.641562 0.325385 0.044 Uiso 1 1 calc R U . . .
H54C H 0.114561 0.528091 0.278001 0.044 Uiso 1 1 calc R U . . .
C55 C 0.64559(9) 0.23230(13) 0.63935(8) 0.0333(3) Uani 0.95 1 d . . P A 1
C56 C 0.68755(9) 0.22124(19) 0.68969(11) 0.0462(5) Uani 0.95 1 d . . P A 1
H56 H 0.721359 0.212318 0.730260 0.055 Uiso 0.95 1 calc R U P A 1
I1 I 0.67174(16) 0.2332(2) 0.66539(14) 0.0338(5) Uiso 0.05 1 d . . P A 2


_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
O1 C10 1.3837(11) . ?
O1 C9 1.4543(11) . ?
N1 C9 1.4315(13) . ?
N1 C16 1.4706(12) . ?
N1 C8 1.4726(13) . ?
C1 C6 1.3979(14) . ?
C1 C2 1.3989(14) . ?
C1 C25 1.4467(15) . ?
C2 C3 1.3851(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3976(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3959(13) . ?
C4 C7 1.5144(14) . ?
C5 C6 1.3852(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5280(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3963(13) . ?
C10 C11 1.4101(13) . ?
C11 C12 1.3979(13) . ?
C11 C21 1.5361(13) . ?
C12 C13 1.3954(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3927(13) . ?
C13 C17 1.5352(13) . ?
C14 C15 1.3893(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.5145(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.5295(14) . ?
C17 C18 1.5324(15) . ?
C17 C19 1.5381(15) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5343(15) . ?
C21 C23 1.5382(14) . ?
C21 C24 1.5395(14) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.1811(15) . ?
C26 H26 0.9500 . ?
O2 C40 1.3808(11) . ?
O2 C39 1.4514(12) . ?
N2 C39 1.4195(14) . ?
N2 C38 1.4642(14) . ?
N2 C46 1.4666(13) . ?
C31 C36 1.3962(15) . ?
C31 C32 1.3974(15) . ?
C31 C55 1.417(2) . ?
C31 I1 2.065(3) . ?
C32 C33 1.3835(16) . ?
C32 H32 0.9500 . ?
C33 C34 1.3997(14) . ?
C33 H33 0.9500 . ?
C34 C35 1.3924(15) . ?
C34 C37 1.5013(16) . ?
C35 C36 1.3841(16) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.5399(14) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C45 1.3924(14) . ?
C40 C41 1.4087(13) . ?
C41 C42 1.3956(13) . ?
C41 C51 1.5358(14) . ?
C42 C43 1.3980(14) . ?
C42 H42 0.9500 . ?
C43 C44 1.3937(14) . ?
C43 C47 1.5310(14) . ?
C44 C45 1.3907(14) . ?
C44 H44 0.9500 . ?
C45 C46 1.5212(14) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C50 1.5273(16) . ?
C47 C49 1.5287(16) . ?
C47 C48 1.5360(16) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C53 1.5372(15) . ?
C51 C54 1.5372(15) . ?
C51 C52 1.5404(15) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 C56 1.179(2) . ?
C56 H56 0.9500 . ?

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
C10 O1 C9 114.07(7) . . ?
C9 N1 C16 108.21(8) . . ?
C9 N1 C8 112.57(8) . . ?
C16 N1 C8 113.74(8) . . ?
C6 C1 C2 118.41(9) . . ?
C6 C1 C25 120.50(9) . . ?
C2 C1 C25 121.08(9) . . ?
C3 C2 C1 120.25(9) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.64(9) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.72(9) . . ?
C5 C4 C7 122.60(9) . . ?
C3 C4 C7 119.68(9) . . ?
C6 C5 C4 121.10(9) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.85(9) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C4 C7 C8 114.70(8) . . ?
C4 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C4 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 111.30(8) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 O1 113.91(8) . . ?
N1 C9 H9A 108.8 . . ?
O1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
O1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C15 120.18(8) . . ?
O1 C10 C11 118.62(8) . . ?
C15 C10 C11 121.19(8) . . ?
C12 C11 C10 116.66(8) . . ?
C12 C11 C21 121.26(8) . . ?
C10 C11 C21 122.05(8) . . ?
C13 C12 C11 123.79(9) . . ?
C13 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C14 C13 C12 117.18(8) . . ?
C14 C13 C17 119.71(8) . . ?
C12 C13 C17 123.11(8) . . ?
C15 C14 C13 121.71(9) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C10 119.47(8) . . ?
C14 C15 C16 119.81(8) . . ?
C10 C15 C16 120.70(8) . . ?
N1 C16 C15 113.01(8) . . ?
N1 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
N1 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C20 C17 C18 108.08(9) . . ?
C20 C17 C13 112.26(8) . . ?
C18 C17 C13 109.53(8) . . ?
C20 C17 C19 108.32(9) . . ?
C18 C17 C19 109.53(9) . . ?
C13 C17 C19 109.08(8) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C11 110.43(8) . . ?
C22 C21 C23 106.83(9) . . ?
C11 C21 C23 112.18(8) . . ?
C22 C21 C24 110.29(9) . . ?
C11 C21 C24 109.89(8) . . ?
C23 C21 C24 107.13(9) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C1 178.63(11) . . ?
C25 C26 H26 180.0 . . ?
C40 O2 C39 113.64(8) . . ?
C39 N2 C38 115.27(9) . . ?
C39 N2 C46 109.56(8) . . ?
C38 N2 C46 115.15(8) . . ?
C36 C31 C32 118.91(10) . . ?
C36 C31 C55 120.28(10) . . ?
C32 C31 C55 120.67(10) . . ?
C36 C31 I1 119.08(11) . . ?
C32 C31 I1 121.96(11) . . ?
C33 C32 C31 120.10(10) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 121.35(10) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 117.92(10) . . ?
C35 C34 C37 121.18(9) . . ?
C33 C34 C37 120.90(9) . . ?
C36 C35 C34 121.26(10) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C31 120.37(10) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C34 C37 C38 110.82(8) . . ?
C34 C37 H37A 109.5 . . ?
C38 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 108.1 . . ?
N2 C38 C37 117.58(8) . . ?
N2 C38 H38A 107.9 . . ?
C37 C38 H38A 107.9 . . ?
N2 C38 H38B 107.9 . . ?
C37 C38 H38B 107.9 . . ?
H38A C38 H38B 107.2 . . ?
N2 C39 O2 114.61(8) . . ?
N2 C39 H39A 108.6 . . ?
O2 C39 H39A 108.6 . . ?
N2 C39 H39B 108.6 . . ?
O2 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
O2 C40 C45 120.53(9) . . ?
O2 C40 C41 118.03(8) . . ?
C45 C40 C41 121.44(9) . . ?
C42 C41 C40 116.74(9) . . ?
C42 C41 C51 121.69(8) . . ?
C40 C41 C51 121.55(8) . . ?
C41 C42 C43 123.55(9) . . ?
C41 C42 H42 118.2 . . ?
C43 C42 H42 118.2 . . ?
C44 C43 C42 117.24(9) . . ?
C44 C43 C47 120.02(9) . . ?
C42 C43 C47 122.72(9) . . ?
C45 C44 C43 121.65(9) . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
C44 C45 C40 119.30(9) . . ?
C44 C45 C46 119.87(9) . . ?
C40 C45 C46 120.82(9) . . ?
N2 C46 C45 112.99(8) . . ?
N2 C46 H46A 109.0 . . ?
C45 C46 H46A 109.0 . . ?
N2 C46 H46B 109.0 . . ?
C45 C46 H46B 109.0 . . ?
H46A C46 H46B 107.8 . . ?
C50 C47 C49 108.46(10) . . ?
C50 C47 C43 112.15(9) . . ?
C49 C47 C43 109.99(9) . . ?
C50 C47 C48 108.11(10) . . ?
C49 C47 C48 108.99(10) . . ?
C43 C47 C48 109.09(9) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C41 C51 C53 111.86(8) . . ?
C41 C51 C54 109.25(8) . . ?
C53 C51 C54 107.71(9) . . ?
C41 C51 C52 110.59(8) . . ?
C53 C51 C52 106.79(9) . . ?
C54 C51 C52 110.59(9) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C56 C55 C31 175.53(15) . . ?
C55 C56 H56 180.0 . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1835726'
loop_
_audit_author_name
_audit_author_address
'Nurbey Gulia'
;University of WrocBaw
Poland
;
_audit_update_record             
;
2018-04-13 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
3-(4-bromophenethyl)-6,8-di-tert-butyl-3,4-dihydro-2H-benzo[e][1,3]oxazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 Br N O'
_chemical_formula_sum            'C24 H32 Br N O'
_chemical_formula_weight         430.41

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   10.630(2)
_cell_length_b                   9.950(2)
_cell_length_c                   40.958(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4332.1(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9451
_cell_measurement_theta_min      2.7983
_cell_measurement_theta_max      34.9968

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.911
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            59380
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -65
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         35.077
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9425
_reflns_number_gt                5200
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0354P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9425
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_restrained_S_all      0.837
_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
Br1 Br -0.36339(2) -0.01743(2) 0.02288(2) 0.02501(4) Uani 1 1 d . . . . .
O1 O 0.32804(8) -0.14370(8) 0.15866(2) 0.01867(18) Uani 1 1 d . . . . .
N1 N 0.33459(9) -0.18388(10) 0.10032(3) 0.0190(2) Uani 1 1 d . . . . .
C1 C -0.18916(12) -0.03271(13) 0.03267(3) 0.0193(2) Uani 1 1 d . . . . .
C2 C -0.12812(12) 0.06982(13) 0.04903(3) 0.0225(3) Uani 1 1 d . . . . .
H2 H -0.1718 0.1495 0.0550 0.027 Uiso 1 1 calc R U . . .
C3 C -0.00182(12) 0.05391(13) 0.05661(3) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.0412 0.1237 0.0678 0.029 Uiso 1 1 calc R U . . .
C4 C 0.06292(12) -0.06223(13) 0.04808(3) 0.0226(3) Uani 1 1 d . . . . .
C5 C -0.00162(13) -0.16228(14) 0.03136(3) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.0415 -0.2420 0.0252 0.031 Uiso 1 1 calc R U . . .
C6 C -0.12807(12) -0.14798(12) 0.02339(3) 0.0228(2) Uani 1 1 d . . . . .
H6 H -0.1712 -0.2166 0.0118 0.027 Uiso 1 1 calc R U . . .
C7 C 0.19870(12) -0.08271(15) 0.05737(3) 0.0278(3) Uani 1 1 d . . . . .
H7A H 0.2461 0.0013 0.0533 0.033 Uiso 1 1 calc R U . . .
H7B H 0.2355 -0.1541 0.0435 0.033 Uiso 1 1 calc R U . . .
C8 C 0.21221(11) -0.12218(12) 0.09334(3) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.2019 -0.0411 0.1071 0.024 Uiso 1 1 calc R U . . .
H8B H 0.1445 -0.1862 0.0992 0.024 Uiso 1 1 calc R U . . .
C9 C 0.34004(12) -0.24091(12) 0.13248(3) 0.0216(3) Uani 1 1 d . . . . .
H9A H 0.4211 -0.2887 0.1350 0.026 Uiso 1 1 calc R U . . .
H9B H 0.2719 -0.3082 0.1347 0.026 Uiso 1 1 calc R U . . .
C10 C 0.40490(10) -0.03248(11) 0.15558(3) 0.0149(2) Uani 1 1 d . . . . .
C11 C 0.42107(10) 0.05006(11) 0.18330(3) 0.0141(2) Uani 1 1 d . . . . .
C12 C 0.49985(11) 0.16037(11) 0.17952(3) 0.0154(2) Uani 1 1 d . . . . .
H12 H 0.5124 0.2176 0.1978 0.018 Uiso 1 1 calc R U . . .
C13 C 0.56212(10) 0.19236(11) 0.15028(3) 0.0154(2) Uani 1 1 d . . . . .
C14 C 0.54013(10) 0.10966(12) 0.12362(3) 0.0160(2) Uani 1 1 d . . . . .
H14 H 0.5792 0.1300 0.1034 0.019 Uiso 1 1 calc R U . . .
C15 C 0.46193(10) -0.00271(11) 0.12586(3) 0.0160(2) Uani 1 1 d . . . . .
C16 C 0.44174(11) -0.09207(12) 0.09650(3) 0.0197(3) Uani 1 1 d . . . . .
H16A H 0.4277 -0.0350 0.0770 0.024 Uiso 1 1 calc R U . . .
H16B H 0.5189 -0.1455 0.0927 0.024 Uiso 1 1 calc R U . . .
C17 C 0.64761(11) 0.31597(11) 0.14860(3) 0.0171(2) Uani 1 1 d . . . . .
C18 C 0.71224(13) 0.32799(14) 0.11545(3) 0.0297(3) Uani 1 1 d . . . . .
H18A H 0.7636 0.2478 0.1115 0.045 Uiso 1 1 calc R U . . .
H18B H 0.7661 0.4079 0.1153 0.045 Uiso 1 1 calc R U . . .
H18C H 0.6485 0.3359 0.0983 0.045 Uiso 1 1 calc R U . . .
C19 C 0.56973(12) 0.44291(13) 0.15461(4) 0.0305(3) Uani 1 1 d . . . . .
H19A H 0.5024 0.4486 0.1383 0.046 Uiso 1 1 calc R U . . .
H19B H 0.6241 0.5221 0.1528 0.046 Uiso 1 1 calc R U . . .
H19C H 0.5328 0.4393 0.1765 0.046 Uiso 1 1 calc R U . . .
C20 C 0.75082(12) 0.30782(13) 0.17500(3) 0.0224(3) Uani 1 1 d . . . . .
H20A H 0.7116 0.3005 0.1966 0.034 Uiso 1 1 calc R U . . .
H20B H 0.8029 0.3890 0.1742 0.034 Uiso 1 1 calc R U . . .
H20C H 0.8036 0.2287 0.1710 0.034 Uiso 1 1 calc R U . . .
C21 C 0.35940(11) 0.01659(11) 0.21616(3) 0.0156(2) Uani 1 1 d . . . . .
C22 C 0.38504(11) 0.12399(12) 0.24208(3) 0.0216(3) Uani 1 1 d . . . . .
H22A H 0.4759 0.1310 0.2458 0.032 Uiso 1 1 calc R U . . .
H22B H 0.3431 0.0990 0.2625 0.032 Uiso 1 1 calc R U . . .
H22C H 0.3526 0.2108 0.2345 0.032 Uiso 1 1 calc R U . . .
C23 C 0.41311(12) -0.11677(12) 0.22887(3) 0.0215(3) Uani 1 1 d . . . . .
H23A H 0.3984 -0.1876 0.2127 0.032 Uiso 1 1 calc R U . . .
H23B H 0.3715 -0.1407 0.2494 0.032 Uiso 1 1 calc R U . . .
H23C H 0.5037 -0.1071 0.2326 0.032 Uiso 1 1 calc R U . . .
C24 C 0.21580(11) 0.00597(12) 0.21227(3) 0.0218(3) Uani 1 1 d . . . . .
H24A H 0.1833 0.0892 0.2026 0.033 Uiso 1 1 calc R U . . .
H24B H 0.1771 -0.0081 0.2337 0.033 Uiso 1 1 calc R U . . .
H24C H 0.1955 -0.0699 0.1980 0.033 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
Br1 C1 1.9010(13) . ?
O1 C10 1.3813(14) . ?
O1 C9 1.4496(14) . ?
N1 C9 1.4356(17) . ?
N1 C8 1.4666(15) . ?
N1 C16 1.4684(15) . ?
C1 C6 1.3717(18) . ?
C1 C2 1.3824(18) . ?
C2 C3 1.3871(18) . ?
C3 C4 1.3897(18) . ?
C4 C5 1.3894(18) . ?
C4 C7 1.5065(18) . ?
C5 C6 1.3905(18) . ?
C7 C8 1.5317(18) . ?
C10 C15 1.3917(16) . ?
C10 C11 1.4117(16) . ?
C11 C12 1.3893(15) . ?
C11 C21 1.5338(16) . ?
C12 C13 1.4046(16) . ?
C13 C14 1.3872(16) . ?
C13 C17 1.5308(16) . ?
C14 C15 1.3963(15) . ?
C15 C16 1.5109(16) . ?
C17 C18 1.5264(18) . ?
C17 C19 1.5300(17) . ?
C17 C20 1.5425(17) . ?
C21 C22 1.5307(16) . ?
C21 C23 1.5355(16) . ?
C21 C24 1.5384(16) . ?

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
C10 O1 C9 114.52(9) . . ?
C9 N1 C8 112.33(10) . . ?
C9 N1 C16 108.21(10) . . ?
C8 N1 C16 114.01(10) . . ?
C6 C1 C2 121.95(12) . . ?
C6 C1 Br1 118.02(9) . . ?
C2 C1 Br1 120.03(10) . . ?
C1 C2 C3 118.59(12) . . ?
C2 C3 C4 121.19(12) . . ?
C5 C4 C3 118.38(12) . . ?
C5 C4 C7 120.04(12) . . ?
C3 C4 C7 121.56(12) . . ?
C4 C5 C6 121.31(12) . . ?
C1 C6 C5 118.57(12) . . ?
C4 C7 C8 111.56(10) . . ?
N1 C8 C7 112.20(10) . . ?
N1 C9 O1 114.29(10) . . ?
O1 C10 C15 120.53(10) . . ?
O1 C10 C11 117.69(10) . . ?
C15 C10 C11 121.77(10) . . ?
C12 C11 C10 116.32(11) . . ?
C12 C11 C21 121.81(10) . . ?
C10 C11 C21 121.83(10) . . ?
C11 C12 C13 123.93(11) . . ?
C14 C13 C12 117.21(10) . . ?
C14 C13 C17 122.76(11) . . ?
C12 C13 C17 120.01(10) . . ?
C13 C14 C15 121.57(11) . . ?
C10 C15 C14 119.16(11) . . ?
C10 C15 C16 120.60(10) . . ?
C14 C15 C16 120.23(11) . . ?
N1 C16 C15 113.04(10) . . ?
C18 C17 C19 108.77(11) . . ?
C18 C17 C13 111.73(10) . . ?
C19 C17 C13 109.56(10) . . ?
C18 C17 C20 107.91(10) . . ?
C19 C17 C20 108.39(10) . . ?
C13 C17 C20 110.39(10) . . ?
C22 C21 C11 112.39(9) . . ?
C22 C21 C23 107.58(10) . . ?
C11 C21 C23 109.04(9) . . ?
C22 C21 C24 107.25(10) . . ?
C11 C21 C24 110.36(10) . . ?
C23 C21 C24 110.17(10) . . ?

_refine_diff_density_max         0.713
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.066

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

data_20
_database_code_depnum_ccdc_archive 'CCDC 1860481'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-10 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H48 N2 O2'
_chemical_formula_sum            'C44 H48 N2 O2'
_chemical_formula_weight         636.84

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.999(2)
_cell_length_b                   9.670(3)
_cell_length_c                   30.784(9)
_cell_angle_alpha                81.78(3)
_cell_angle_beta                 86.06(4)
_cell_angle_gamma                79.82(3)
_cell_volume                     1737.9(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1602
_cell_measurement_theta_min      3.1406
_cell_measurement_theta_max      28.6960

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            12858
_diffrn_reflns_av_unetI/netI     0.2653
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.139
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             6654
_reflns_number_gt                2184
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1539P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6654
_refine_ls_number_parameters     470
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.2942
_refine_ls_R_factor_gt           0.1372
_refine_ls_wR_factor_ref         0.3697
_refine_ls_wR_factor_gt          0.3076
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.996
_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
O1 O 1.5275(9) 0.9350(6) 0.69882(17) 0.0418(14) Uani 1 1 d . U . . .
O2 O -0.6427(9) 0.5890(6) 0.21664(18) 0.0507(16) Uani 1 1 d . U . . .
N1 N 1.1955(10) 1.0754(7) 0.6645(2) 0.0355(16) Uani 1 1 d . U . . .
N2 N -0.3004(11) 0.6375(7) 0.2443(2) 0.0364(16) Uani 1 1 d . U . . .
C1 C 0.8340(14) 0.7663(9) 0.5176(2) 0.039(2) Uani 1 1 d . U . . .
C2 C 0.7533(14) 0.8957(9) 0.5316(3) 0.046(2) Uani 1 1 d . U . . .
H2 H 0.606094 0.943218 0.523810 0.055 Uiso 1 1 calc R U . . .
C3 C 0.8777(14) 0.9582(9) 0.5562(3) 0.047(2) Uani 1 1 d . U . . .
H3 H 0.816635 1.047709 0.565194 0.057 Uiso 1 1 calc R U . . .
C4 C 1.0928(14) 0.8914(9) 0.5682(2) 0.0367(19) Uani 1 1 d . U . . .
C5 C 1.1756(13) 0.7594(8) 0.5553(2) 0.0370(19) Uani 1 1 d . U . . .
H5 H 1.320733 0.710667 0.563920 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0503(13) 0.6990(8) 0.5302(3) 0.0388(19) Uani 1 1 d . U . . .
H6 H 1.111263 0.609553 0.521170 0.047 Uiso 1 1 calc R U . . .
C7 C 1.2279(14) 0.9614(9) 0.5962(3) 0.046(2) Uani 1 1 d . U . . .
H7A H 1.385821 0.909726 0.597079 0.055 Uiso 1 1 calc R U . . .
H7B H 1.232108 1.059923 0.582406 0.055 Uiso 1 1 calc R U . . .
C8 C 1.1285(14) 0.9637(9) 0.6430(2) 0.039(2) Uani 1 1 d . U . . .
H8A H 0.961090 0.978585 0.642530 0.047 Uiso 1 1 calc R U . . .
H8B H 1.179239 0.870542 0.660459 0.047 Uiso 1 1 calc R U . . .
C9 C 1.4305(13) 1.0604(8) 0.6696(3) 0.0374(19) Uani 1 1 d . U . . .
H9A H 1.461260 1.145514 0.680998 0.045 Uiso 1 1 calc R U . . .
H9B H 1.508855 1.057237 0.640298 0.045 Uiso 1 1 calc R U . . .
C10 C 1.4058(13) 0.9138(9) 0.7377(3) 0.0384(19) Uani 1 1 d . U . . .
C11 C 1.5019(14) 0.8180(9) 0.7705(3) 0.041(2) Uani 1 1 d . U . . .
H11 H 1.650410 0.767335 0.765810 0.049 Uiso 1 1 calc R U . . .
C12 C 1.3878(14) 0.7923(9) 0.8107(3) 0.044(2) Uani 1 1 d . U . . .
H12 H 1.459090 0.723751 0.832958 0.053 Uiso 1 1 calc R U . . .
C13 C 1.1682(12) 0.8658(9) 0.8192(2) 0.0358(19) Uani 1 1 d . U . . .
C14 C 1.0725(13) 0.9575(8) 0.7843(3) 0.0356(19) Uani 1 1 d . U . . .
H14 H 0.921828 1.005509 0.788584 0.043 Uiso 1 1 calc R U . . .
C15 C 1.1801(13) 0.9847(8) 0.7436(2) 0.0317(17) Uani 1 1 d . U . . .
C16 C 1.0713(13) 1.0910(8) 0.7076(2) 0.0371(19) Uani 1 1 d . U . . .
H16A H 0.912528 1.078013 0.705455 0.044 Uiso 1 1 calc R U . . .
H16B H 1.069011 1.187841 0.714690 0.044 Uiso 1 1 calc R U . . .
C17 C 1.0486(14) 0.8378(10) 0.8647(3) 0.049(2) Uani 1 1 d . U . . .
C18 C 0.9794(16) 0.6925(10) 0.8693(3) 0.057(2) Uani 1 1 d . U . . .
H18A H 0.885548 0.688038 0.844873 0.085 Uiso 1 1 calc R U . . .
H18B H 0.892778 0.676110 0.897163 0.085 Uiso 1 1 calc R U . . .
H18C H 1.115404 0.619597 0.868834 0.085 Uiso 1 1 calc R U . . .
C19 C 1.2091(15) 0.8427(13) 0.8999(3) 0.072(3) Uani 1 1 d . U . . .
H19A H 1.334069 0.762346 0.899921 0.108 Uiso 1 1 calc R U . . .
H19B H 1.127520 0.837545 0.928650 0.108 Uiso 1 1 calc R U . . .
H19C H 1.269845 0.931570 0.894080 0.108 Uiso 1 1 calc R U . . .
C20 C 0.8358(13) 0.9494(10) 0.8703(3) 0.049(2) Uani 1 1 d . U . . .
H20A H 0.877767 1.043993 0.865983 0.073 Uiso 1 1 calc R U . . .
H20B H 0.767263 0.930821 0.899885 0.073 Uiso 1 1 calc R U . . .
H20C H 0.726617 0.944498 0.848499 0.073 Uiso 1 1 calc R U . . .
C21 C 0.7013(14) 0.7108(9) 0.4895(2) 0.041(2) Uani 1 1 d . U . . .
C22 C 0.5856(14) 0.6663(9) 0.4661(3) 0.044(2) Uani 1 1 d . U . . .
C31 C 0.2098(13) 0.5289(9) 0.3838(3) 0.0392(19) Uani 1 1 d . U . . .
C32 C 0.2979(13) 0.4100(9) 0.3627(3) 0.042(2) Uani 1 1 d . U . . .
H32 H 0.443841 0.357901 0.369379 0.051 Uiso 1 1 calc R U . . .
C33 C 0.1736(13) 0.3687(9) 0.3323(3) 0.042(2) Uani 1 1 d . U . . .
H33 H 0.237786 0.289670 0.317738 0.050 Uiso 1 1 calc R U . . .
C34 C -0.0434(12) 0.4396(8) 0.3222(2) 0.0331(18) Uani 1 1 d . U . . .
C35 C -0.1296(14) 0.5526(9) 0.3447(3) 0.041(2) Uani 1 1 d . U . . .
H35 H -0.276424 0.604034 0.338317 0.049 Uiso 1 1 calc R U . . .
C36 C -0.0128(13) 0.5929(9) 0.3756(3) 0.041(2) Uani 1 1 d . U . . .
H36 H -0.084180 0.666230 0.391898 0.049 Uiso 1 1 calc R U . . .
C37 C -0.1720(13) 0.3990(9) 0.2867(2) 0.0378(19) Uani 1 1 d . U . . .
H37A H -0.105655 0.301054 0.281640 0.045 Uiso 1 1 calc R U . . .
H37B H -0.330910 0.398371 0.297673 0.045 Uiso 1 1 calc R U . . .
C38 C -0.1738(12) 0.4924(8) 0.2436(2) 0.0353(19) Uani 1 1 d . U . . .
H38A H -0.015118 0.498474 0.233458 0.042 Uiso 1 1 calc R U . . .
H38B H -0.240344 0.447426 0.221807 0.042 Uiso 1 1 calc R U . . .
C39 C -0.5409(13) 0.6401(9) 0.2508(3) 0.043(2) Uani 1 1 d . U . . .
H39A H -0.570321 0.581901 0.279088 0.052 Uiso 1 1 calc R U . . .
H39B H -0.615735 0.738771 0.253104 0.052 Uiso 1 1 calc R U . . .
C40 C -0.5655(13) 0.6299(9) 0.1745(3) 0.0376(19) Uani 1 1 d . U . . .
C41 C -0.6696(15) 0.5942(9) 0.1407(3) 0.053(2) Uani 1 1 d . U . . .
H41 H -0.793130 0.544140 0.147245 0.064 Uiso 1 1 calc R U . . .
C42 C -0.6028(14) 0.6276(9) 0.0977(3) 0.045(2) Uani 1 1 d . U . . .
H42 H -0.684439 0.605344 0.074978 0.054 Uiso 1 1 calc R U . . .
C43 C -0.4169(14) 0.6936(10) 0.0873(3) 0.051(2) Uani 1 1 d . U . . .
C44 C -0.3105(14) 0.7284(10) 0.1224(3) 0.050(2) Uani 1 1 d . U . . .
H44 H -0.186513 0.778129 0.116017 0.059 Uiso 1 1 calc R U . . .
C45 C -0.3765(12) 0.6942(8) 0.1658(2) 0.0338(18) Uani 1 1 d . U . . .
C46 C -0.2631(15) 0.7303(9) 0.2026(3) 0.047(2) Uani 1 1 d . U . . .
H46A H -0.321227 0.830227 0.206719 0.056 Uiso 1 1 calc R U . . .
H46B H -0.098303 0.721429 0.195336 0.056 Uiso 1 1 calc R U . . .
C47 C -0.3363(16) 0.7260(11) 0.0396(3) 0.074(3) Uani 1 1 d D U . . .
C51 C 0.3395(14) 0.5755(9) 0.4145(3) 0.042(2) Uani 1 1 d . U . . .
C52 C 0.4531(14) 0.6179(9) 0.4388(3) 0.044(2) Uani 1 1 d . U . . .
C48 C -0.303(5) 0.565(2) 0.0262(8) 0.073(6) Uani 0.47(2) 1 d D U P A 1
H48A H -0.166979 0.507499 0.039354 0.110 Uiso 0.47(2) 1 calc R U P A 1
H48B H -0.286984 0.569133 -0.005878 0.110 Uiso 0.47(2) 1 calc R U P A 1
H48C H -0.435847 0.521553 0.037000 0.110 Uiso 0.47(2) 1 calc R U P A 1
C49 C -0.521(4) 0.825(3) 0.0128(10) 0.064(7) Uani 0.47(2) 1 d D U P A 1
H49A H -0.659067 0.782797 0.015368 0.096 Uiso 0.47(2) 1 calc R U P A 1
H49B H -0.468590 0.839058 -0.018105 0.096 Uiso 0.47(2) 1 calc R U P A 1
H49C H -0.553563 0.916706 0.024062 0.096 Uiso 0.47(2) 1 calc R U P A 1
C50 C -0.120(3) 0.770(3) 0.0283(8) 0.069(6) Uani 0.47(2) 1 d D U P A 1
H50A H -0.123865 0.864381 0.036439 0.103 Uiso 0.47(2) 1 calc R U P A 1
H50B H -0.086991 0.771555 -0.003339 0.103 Uiso 0.47(2) 1 calc R U P A 1
H50C H -0.001554 0.702364 0.044283 0.103 Uiso 0.47(2) 1 calc R U P A 1
C48A C -0.179(4) 0.610(2) 0.0223(7) 0.068(6) Uani 0.53(2) 1 d D U P A 2
H48D H -0.045743 0.583421 0.040331 0.101 Uiso 0.53(2) 1 calc R U P A 2
H48E H -0.131102 0.640981 -0.008093 0.101 Uiso 0.53(2) 1 calc R U P A 2
H48F H -0.255027 0.527748 0.023065 0.101 Uiso 0.53(2) 1 calc R U P A 2
C49A C -0.536(4) 0.775(3) 0.0102(8) 0.051(5) Uani 0.53(2) 1 d D U P A 2
H49D H -0.617099 0.696243 0.009332 0.076 Uiso 0.53(2) 1 calc R U P A 2
H49E H -0.480493 0.807661 -0.019553 0.076 Uiso 0.53(2) 1 calc R U P A 2
H49F H -0.638321 0.853240 0.021832 0.076 Uiso 0.53(2) 1 calc R U P A 2
C50A C -0.181(3) 0.850(2) 0.0366(6) 0.052(5) Uani 0.53(2) 1 d D U P A 2
H50D H -0.047461 0.815139 0.054253 0.078 Uiso 0.53(2) 1 calc R U P A 2
H50E H -0.269780 0.933573 0.047820 0.078 Uiso 0.53(2) 1 calc R U P A 2
H50F H -0.131740 0.875498 0.005917 0.078 Uiso 0.53(2) 1 calc R U P A 2


_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
O1 C10 1.368(9) . ?
O1 C9 1.459(9) . ?
O2 C40 1.375(9) . ?
O2 C39 1.437(9) . ?
N1 C9 1.408(9) . ?
N1 C8 1.470(9) . ?
N1 C16 1.488(9) . ?
N2 C39 1.439(9) . ?
N2 C38 1.475(9) . ?
N2 C46 1.485(10) . ?
C1 C2 1.377(11) . ?
C1 C6 1.399(11) . ?
C1 C21 1.432(11) . ?
C2 C3 1.366(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(11) . ?
C4 C7 1.523(11) . ?
C5 C6 1.365(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.522(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.353(10) . ?
C10 C15 1.418(10) . ?
C11 C12 1.385(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.409(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(10) . ?
C13 C17 1.539(11) . ?
C14 C15 1.382(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.501(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.511(11) . ?
C17 C18 1.518(12) . ?
C17 C20 1.536(12) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.202(11) . ?
C22 C52 1.377(12) . ?
C31 C36 1.393(10) . ?
C31 C32 1.406(11) . ?
C31 C51 1.431(11) . ?
C32 C33 1.379(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.393(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(10) . ?
C34 C37 1.513(10) . ?
C35 C36 1.357(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.494(10) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.365(11) . ?
C40 C45 1.379(10) . ?
C41 C42 1.366(11) . ?
C41 H41 0.9500 . ?
C42 C43 1.378(11) . ?
C42 H42 0.9500 . ?
C43 C44 1.401(11) . ?
C43 C47 1.521(13) . ?
C44 C45 1.375(11) . ?
C44 H44 0.9500 . ?
C45 C46 1.476(10) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C50 1.440(16) . ?
C47 C48A 1.471(15) . ?
C47 C49A 1.517(16) . ?
C47 C49 1.533(17) . ?
C47 C50A 1.633(15) . ?
C47 C48 1.645(16) . ?
C51 C52 1.203(10) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C48A H48D 0.9800 . ?
C48A H48E 0.9800 . ?
C48A H48F 0.9800 . ?
C49A H49D 0.9800 . ?
C49A H49E 0.9800 . ?
C49A H49F 0.9800 . ?
C50A H50D 0.9800 . ?
C50A H50E 0.9800 . ?
C50A H50F 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
C10 O1 C9 113.8(6) . . ?
C40 O2 C39 115.7(6) . . ?
C9 N1 C8 114.3(6) . . ?
C9 N1 C16 109.9(6) . . ?
C8 N1 C16 112.3(6) . . ?
C39 N2 C38 112.2(6) . . ?
C39 N2 C46 107.2(6) . . ?
C38 N2 C46 111.6(6) . . ?
C2 C1 C6 117.1(8) . . ?
C2 C1 C21 119.5(8) . . ?
C6 C1 C21 123.3(8) . . ?
C3 C2 C1 122.3(8) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 120.2(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.5(8) . . ?
C3 C4 C7 119.6(7) . . ?
C5 C4 C7 121.9(8) . . ?
C6 C5 C4 120.6(8) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.3(8) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C4 112.7(7) . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C7 112.7(6) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 O1 115.0(6) . . ?
N1 C9 H9A 108.5 . . ?
O1 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
O1 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 O1 118.5(7) . . ?
C11 C10 C15 119.8(7) . . ?
O1 C10 C15 121.6(7) . . ?
C10 C11 C12 121.2(8) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 121.3(8) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 115.5(7) . . ?
C14 C13 C17 124.4(7) . . ?
C12 C13 C17 120.1(7) . . ?
C13 C14 C15 124.7(7) . . ?
C13 C14 H14 117.6 . . ?
C15 C14 H14 117.6 . . ?
C14 C15 C10 117.3(7) . . ?
C14 C15 C16 122.3(7) . . ?
C10 C15 C16 120.3(7) . . ?
N1 C16 C15 111.4(6) . . ?
N1 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C19 C17 C18 110.2(8) . . ?
C19 C17 C20 108.4(7) . . ?
C18 C17 C20 108.9(7) . . ?
C19 C17 C13 109.3(7) . . ?
C18 C17 C13 108.5(7) . . ?
C20 C17 C13 111.5(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C1 178.5(9) . . ?
C21 C22 C52 178.9(10) . . ?
C36 C31 C32 117.0(7) . . ?
C36 C31 C51 121.9(8) . . ?
C32 C31 C51 121.0(8) . . ?
C33 C32 C31 120.4(8) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 121.9(8) . . ?
C32 C33 H33 119.0 . . ?
C34 C33 H33 119.0 . . ?
C35 C34 C33 116.6(7) . . ?
C35 C34 C37 122.0(7) . . ?
C33 C34 C37 121.3(7) . . ?
C36 C35 C34 122.6(8) . . ?
C36 C35 H35 118.7 . . ?
C34 C35 H35 118.7 . . ?
C35 C36 C31 121.2(8) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
C38 C37 C34 115.9(7) . . ?
C38 C37 H37A 108.3 . . ?
C34 C37 H37A 108.3 . . ?
C38 C37 H37B 108.3 . . ?
C34 C37 H37B 108.3 . . ?
H37A C37 H37B 107.4 . . ?
N2 C38 C37 114.9(6) . . ?
N2 C38 H38A 108.5 . . ?
C37 C38 H38A 108.5 . . ?
N2 C38 H38B 108.5 . . ?
C37 C38 H38B 108.5 . . ?
H38A C38 H38B 107.5 . . ?
O2 C39 N2 114.6(6) . . ?
O2 C39 H39A 108.6 . . ?
N2 C39 H39A 108.6 . . ?
O2 C39 H39B 108.6 . . ?
N2 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
C41 C40 O2 118.0(8) . . ?
C41 C40 C45 119.6(8) . . ?
O2 C40 C45 122.2(7) . . ?
C40 C41 C42 122.5(9) . . ?
C40 C41 H41 118.8 . . ?
C42 C41 H41 118.8 . . ?
C41 C42 C43 119.9(8) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C42 C43 C44 116.9(8) . . ?
C42 C43 C47 120.1(8) . . ?
C44 C43 C47 123.0(9) . . ?
C45 C44 C43 123.3(8) . . ?
C45 C44 H44 118.4 . . ?
C43 C44 H44 118.4 . . ?
C44 C45 C40 117.7(7) . . ?
C44 C45 C46 123.1(8) . . ?
C40 C45 C46 119.1(7) . . ?
C45 C46 N2 112.3(7) . . ?
C45 C46 H46A 109.2 . . ?
N2 C46 H46A 109.2 . . ?
C45 C46 H46B 109.2 . . ?
N2 C46 H46B 109.2 . . ?
H46A C46 H46B 107.9 . . ?
C48A C47 C49A 110.2(14) . . ?
C50 C47 C43 121.1(12) . . ?
C48A C47 C43 115.0(11) . . ?
C49A C47 C43 110.9(13) . . ?
C50 C47 C49 110.0(16) . . ?
C43 C47 C49 111.2(15) . . ?
C48A C47 C50A 102.4(12) . . ?
C49A C47 C50A 110.0(13) . . ?
C43 C47 C50A 107.9(10) . . ?
C50 C47 C48 104.4(14) . . ?
C43 C47 C48 98.5(11) . . ?
C49 C47 C48 110.6(16) . . ?
C52 C51 C31 177.1(10) . . ?
C51 C52 C22 179.2(10) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C47 C48A H48D 109.5 . . ?
C47 C48A H48E 109.5 . . ?
H48D C48A H48E 109.5 . . ?
C47 C48A H48F 109.5 . . ?
H48D C48A H48F 109.5 . . ?
H48E C48A H48F 109.5 . . ?
C47 C49A H49D 109.5 . . ?
C47 C49A H49E 109.5 . . ?
H49D C49A H49E 109.5 . . ?
C47 C49A H49F 109.5 . . ?
H49D C49A H49F 109.5 . . ?
H49E C49A H49F 109.5 . . ?
C47 C50A H50D 109.5 . . ?
C47 C50A H50E 109.5 . . ?
H50D C50A H50E 109.5 . . ?
C47 C50A H50F 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.343
_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_21
_database_code_depnum_ccdc_archive 'CCDC 1860483'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-09-04 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H36 N2 O2'
_chemical_formula_sum            'C38 H36 N2 O2'
_chemical_formula_weight         552.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.746(2)
_cell_length_b                   5.936(2)
_cell_length_c                   51.31(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.31(3)
_cell_angle_gamma                90
_cell_volume                     1445.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6618
_cell_measurement_theta_min      1.7204
_cell_measurement_theta_max      69.9794

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_reflns_number            10335
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         70.112
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2687
_reflns_number_gt                2366
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1339P)²+0.8860P] 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         2687
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
O1 O 0.0999(3) -0.2011(3) 0.64180(3) 0.0325(4) Uani 1 1 d . . . . .
N1 N -0.1097(4) 0.1586(3) 0.63010(3) 0.0297(5) Uani 1 1 d . . . . .
C1 C 0.6454(4) 0.6670(4) 0.54034(4) 0.0279(5) Uani 1 1 d . . . . .
C2 C 0.5687(5) 0.4493(4) 0.53280(4) 0.0300(5) Uani 1 1 d . . . . .
H2 H 0.641825 0.386689 0.517200 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3859(4) 0.3246(4) 0.54806(4) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.331005 0.178701 0.542363 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2808(4) 0.4061(4) 0.57137(4) 0.0276(5) Uani 1 1 d . . . . .
C5 C 0.3675(4) 0.6222(4) 0.57945(4) 0.0286(5) Uani 1 1 d . . . . .
H5 H 0.302571 0.680643 0.595577 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5453(5) 0.7502(4) 0.56428(4) 0.0301(5) Uani 1 1 d . . . . .
H6 H 0.600906 0.895797 0.570034 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0680(4) 0.2722(4) 0.58678(4) 0.0324(5) Uani 1 1 d . . . . .
H7A H 0.057469 0.118154 0.579447 0.039 Uiso 1 1 calc R U . . .
H7B H -0.119600 0.342673 0.584501 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1324(4) 0.2550(4) 0.61587(4) 0.0299(5) Uani 1 1 d . . . . .
H8A H 0.300146 0.158467 0.618583 0.036 Uiso 1 1 calc R U . . .
H8B H 0.175734 0.406602 0.622852 0.036 Uiso 1 1 calc R U . . .
C9 C -0.1298(5) -0.0792(4) 0.62860(4) 0.0324(5) Uani 1 1 d . . . . .
H9A H -0.132860 -0.123860 0.610012 0.039 Uiso 1 1 calc R U . . .
H9B H -0.311019 -0.126578 0.636337 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1805(4) -0.1113(4) 0.66540(4) 0.0280(5) Uani 1 1 d . . . . .
C11 C 0.3754(5) -0.2352(4) 0.67999(4) 0.0332(5) Uani 1 1 d . . . . .
H11 H 0.439004 -0.377463 0.673896 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4756(5) -0.1495(4) 0.70343(4) 0.0359(6) Uani 1 1 d . . . . .
H12 H 0.607444 -0.234729 0.713339 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3864(5) 0.0597(5) 0.71275(4) 0.0350(6) Uani 1 1 d . . . . .
C14 C 0.1900(5) 0.1778(4) 0.69782(4) 0.0322(5) Uani 1 1 d . . . . .
H14 H 0.124829 0.319126 0.704040 0.039 Uiso 1 1 calc R U . . .
C15 C 0.0848(4) 0.0979(4) 0.67419(4) 0.0292(5) Uani 1 1 d . . . . .
C16 C -0.1218(5) 0.2280(4) 0.65752(4) 0.0309(5) Uani 1 1 d . . . . .
H16A H -0.314877 0.203593 0.664156 0.037 Uiso 1 1 calc R U . . .
H16B H -0.079315 0.390863 0.658826 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5046(6) 0.1565(5) 0.73778(5) 0.0464(7) Uani 1 1 d . . . . .
H17A H 0.456983 0.316807 0.738885 0.070 Uiso 1 1 calc R U . . .
H17B H 0.709851 0.138666 0.738008 0.070 Uiso 1 1 calc R U . . .
H17C H 0.423450 0.076564 0.752678 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8102(5) 0.8074(4) 0.52364(4) 0.0310(5) Uani 1 1 d . . . . .
C19 C 0.9323(5) 0.9304(4) 0.50862(4) 0.0317(5) 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
O1 C10 1.376(3) . ?
O1 C9 1.470(3) . ?
N1 C9 1.417(3) . ?
N1 C16 1.467(3) . ?
N1 C8 1.480(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.409(3) . ?
C1 C18 1.431(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(3) . ?
C4 C7 1.512(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.396(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C17 1.512(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.510(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.211(3) . ?
C19 C19 1.373(4) 3_776 ?

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
C10 O1 C9 114.64(18) . . ?
C9 N1 C16 109.16(18) . . ?
C9 N1 C8 114.23(19) . . ?
C16 N1 C8 113.52(18) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C18 121.0(2) . . ?
C6 C1 C18 120.4(2) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C7 120.9(2) . . ?
C5 C4 C7 121.3(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C4 C7 C8 114.59(18) . . ?
C4 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C4 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 110.89(17) . . ?
N1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 O1 114.57(18) . . ?
N1 C9 H9A 108.6 . . ?
O1 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
O1 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
O1 C10 C11 116.6(2) . . ?
O1 C10 C15 122.6(2) . . ?
C11 C10 C15 120.7(2) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 117.5(2) . . ?
C14 C13 C17 121.4(2) . . ?
C12 C13 C17 121.1(2) . . ?
C15 C14 C13 122.9(2) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C10 117.9(2) . . ?
C14 C15 C16 123.2(2) . . ?
C10 C15 C16 118.8(2) . . ?
N1 C16 C15 111.80(19) . . ?
N1 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
N1 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C1 175.4(2) . . ?
C18 C19 C19 179.3(3) . 3_776 ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1860484'
loop_
_audit_author_name
_audit_author_address
'Dawid J?drzkiewicz'
;WrocBaw University
Poland
;
_audit_update_record             
;
2018-08-06 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H49 N O'
_chemical_formula_sum            'C28 H49 N O'
_chemical_formula_weight         415.68

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

_space_group_crystal_system      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                   5.696(3)
_cell_length_b                   9.055(4)
_cell_length_c                   50.29(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.34(4)
_cell_angle_gamma                90
_cell_volume                     2592(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2838
_cell_measurement_theta_min      2.7674
_cell_measurement_theta_max      28.8058

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            10947
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.773
_diffrn_reflns_theta_max         28.872
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5928
_reflns_number_gt                3479
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0255P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5928
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
O1 O 0.72060(19) 0.51252(14) 0.11421(2) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.6719(2) 0.33421(17) 0.14933(3) 0.0220(4) Uani 1 1 d . . . . .
C1 C -1.1550(3) 0.3486(2) 0.36184(4) 0.0376(6) Uani 1 1 d . . . . .
H1A H -1.231154 0.261333 0.353815 0.056 Uiso 1 1 calc R U . . .
H1B H -1.273514 0.410697 0.369941 0.056 Uiso 1 1 calc R U . . .
H1C H -1.038102 0.317331 0.375533 0.056 Uiso 1 1 calc R U . . .
C2 C -1.0347(3) 0.4359(2) 0.34049(3) 0.0248(5) Uani 1 1 d . . . . .
H2A H -0.960075 0.524423 0.348718 0.030 Uiso 1 1 calc R U . . .
H2B H -1.154709 0.469960 0.327080 0.030 Uiso 1 1 calc R U . . .
C3 C -0.8490(3) 0.3474(2) 0.32657(4) 0.0242(5) Uani 1 1 d . . . . .
H3A H -0.734458 0.308474 0.340147 0.029 Uiso 1 1 calc R U . . .
H3B H -0.925664 0.261857 0.317554 0.029 Uiso 1 1 calc R U . . .
C4 C -0.7172(3) 0.4351(2) 0.30621(3) 0.0227(4) Uani 1 1 d . . . . .
H4A H -0.630439 0.515980 0.315491 0.027 Uiso 1 1 calc R U . . .
H4B H -0.832885 0.480721 0.293480 0.027 Uiso 1 1 calc R U . . .
C5 C -0.5445(3) 0.3447(2) 0.29066(4) 0.0220(4) Uani 1 1 d . . . . .
H5A H -0.631545 0.265345 0.280966 0.026 Uiso 1 1 calc R U . . .
H5B H -0.430716 0.297160 0.303368 0.026 Uiso 1 1 calc R U . . .
C6 C -0.4099(3) 0.4348(2) 0.27083(3) 0.0211(4) Uani 1 1 d . . . . .
H6A H -0.322157 0.513782 0.280553 0.025 Uiso 1 1 calc R U . . .
H6B H -0.523847 0.482951 0.258215 0.025 Uiso 1 1 calc R U . . .
C7 C -0.2380(3) 0.3449(2) 0.25507(3) 0.0218(4) Uani 1 1 d . . . . .
H7A H -0.326217 0.267366 0.245039 0.026 Uiso 1 1 calc R U . . .
H7B H -0.126204 0.295022 0.267706 0.026 Uiso 1 1 calc R U . . .
C8 C -0.0990(3) 0.4356(2) 0.23561(3) 0.0212(4) Uani 1 1 d . . . . .
H8A H -0.210595 0.486865 0.223139 0.025 Uiso 1 1 calc R U . . .
H8B H -0.008264 0.512016 0.245655 0.025 Uiso 1 1 calc R U . . .
C9 C 0.0693(3) 0.3443(2) 0.21962(4) 0.0228(4) Uani 1 1 d . . . . .
H9A H 0.177968 0.291078 0.232138 0.027 Uiso 1 1 calc R U . . .
H9B H -0.022248 0.269454 0.209281 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2131(3) 0.4336(2) 0.20062(3) 0.0208(4) Uani 1 1 d . . . . .
H10A H 0.310201 0.505742 0.210977 0.025 Uiso 1 1 calc R U . . .
H10B H 0.105056 0.489889 0.188485 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3729(3) 0.3392(2) 0.18412(4) 0.0231(4) Uani 1 1 d . . . . .
H11A H 0.489077 0.289254 0.196220 0.028 Uiso 1 1 calc R U . . .
H11B H 0.277253 0.261811 0.174963 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5033(3) 0.4255(2) 0.16350(3) 0.0214(4) Uani 1 1 d . . . . .
H12A H 0.387867 0.468193 0.150399 0.026 Uiso 1 1 calc R U . . .
H12B H 0.588586 0.508262 0.172396 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8315(3) 0.4221(2) 0.13481(3) 0.0266(5) Uani 1 1 d . . . . .
H13A H 0.946222 0.355864 0.126583 0.032 Uiso 1 1 calc R U . . .
H13B H 0.919980 0.487185 0.147474 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5704(3) 0.4351(2) 0.09689(3) 0.0171(4) Uani 1 1 d . . . . .
C15 C 0.5081(3) 0.5000(2) 0.07221(3) 0.0153(4) Uani 1 1 d . . . . .
C16 C 0.3563(3) 0.41827(19) 0.05539(3) 0.0157(4) Uani 1 1 d . . . . .
H16 H 0.314170 0.458512 0.038410 0.019 Uiso 1 1 calc R U . . .
C17 C 0.2625(3) 0.28091(19) 0.06195(3) 0.0153(4) Uani 1 1 d . . . . .
C18 C 0.3292(3) 0.2238(2) 0.08673(3) 0.0177(4) Uani 1 1 d . . . . .
H18 H 0.268392 0.130856 0.091853 0.021 Uiso 1 1 calc R U . . .
C19 C 0.4822(3) 0.2984(2) 0.10429(3) 0.0175(4) Uani 1 1 d . . . . .
C20 C 0.5576(3) 0.2293(2) 0.13065(3) 0.0245(5) Uani 1 1 d . . . . .
H20A H 0.417969 0.186926 0.138917 0.029 Uiso 1 1 calc R U . . .
H20B H 0.667751 0.147270 0.127376 0.029 Uiso 1 1 calc R U . . .
C21 C 0.1061(3) 0.1926(2) 0.04224(3) 0.0183(4) Uani 1 1 d . . . . .
C22 C -0.0854(3) 0.1099(2) 0.05671(4) 0.0414(6) Uani 1 1 d . . . . .
H22A H -0.012156 0.040775 0.069553 0.062 Uiso 1 1 calc R U . . .
H22B H -0.184442 0.055017 0.043738 0.062 Uiso 1 1 calc R U . . .
H22C H -0.182080 0.180808 0.066100 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2626(3) 0.0807(2) 0.02847(4) 0.0385(6) Uani 1 1 d . . . . .
H23A H 0.385532 0.133256 0.019218 0.058 Uiso 1 1 calc R U . . .
H23B H 0.167002 0.022988 0.015591 0.058 Uiso 1 1 calc R U . . .
H23C H 0.335218 0.014302 0.041821 0.058 Uiso 1 1 calc R U . . .
C24 C -0.0170(3) 0.2885(2) 0.02096(4) 0.0314(5) Uani 1 1 d . . . . .
H24A H -0.115889 0.361675 0.029503 0.047 Uiso 1 1 calc R U . . .
H24B H -0.114971 0.226151 0.009082 0.047 Uiso 1 1 calc R U . . .
H24C H 0.100930 0.339338 0.010646 0.047 Uiso 1 1 calc R U . . .
C25 C 0.6003(3) 0.65207(19) 0.06425(3) 0.0169(4) Uani 1 1 d . . . . .
C26 C 0.5175(3) 0.7701(2) 0.08381(3) 0.0219(4) Uani 1 1 d . . . . .
H26A H 0.576749 0.867018 0.078605 0.033 Uiso 1 1 calc R U . . .
H26B H 0.577753 0.746206 0.101836 0.033 Uiso 1 1 calc R U . . .
H26C H 0.345412 0.772076 0.083453 0.033 Uiso 1 1 calc R U . . .
C27 C 0.8707(3) 0.6530(2) 0.06406(4) 0.0249(5) Uani 1 1 d . . . . .
H27A H 0.923145 0.582307 0.050789 0.037 Uiso 1 1 calc R U . . .
H27B H 0.935634 0.625033 0.081693 0.037 Uiso 1 1 calc R U . . .
H27C H 0.925347 0.752184 0.059574 0.037 Uiso 1 1 calc R U . . .
C28 C 0.5104(3) 0.6967(2) 0.03621(3) 0.0220(4) Uani 1 1 d . . . . .
H28A H 0.575954 0.793077 0.031660 0.033 Uiso 1 1 calc R U . . .
H28B H 0.338520 0.702847 0.035729 0.033 Uiso 1 1 calc R U . . .
H28C H 0.559373 0.622682 0.023348 0.033 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
O1 C14 1.386(2) . ?
O1 C13 1.445(2) . ?
N1 C13 1.431(2) . ?
N1 C20 1.470(2) . ?
N1 C12 1.473(2) . ?
C1 C2 1.519(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.392(2) . ?
C14 C15 1.406(2) . ?
C15 C16 1.397(2) . ?
C15 C25 1.532(2) . ?
C16 C17 1.399(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 C21 1.531(2) . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.512(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C24 1.526(2) . ?
C21 C22 1.532(2) . ?
C21 C23 1.533(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C28 1.534(2) . ?
C25 C26 1.539(2) . ?
C25 C27 1.541(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C14 O1 C13 113.88(14) . . ?
C13 N1 C20 107.90(14) . . ?
C13 N1 C12 112.03(15) . . ?
C20 N1 C12 113.07(14) . . ?
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 113.19(17) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 114.06(16) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 114.43(16) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 113.76(16) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 114.04(15) . . ?
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 . . ?
C6 C7 C8 114.13(16) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 113.72(15) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 114.32(15) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 113.27(15) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 113.87(15) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C11 112.89(15) . . ?
N1 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N1 C13 O1 114.36(14) . . ?
N1 C13 H13A 108.7 . . ?
O1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
O1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O1 C14 C19 120.13(15) . . ?
O1 C14 C15 118.09(16) . . ?
C19 C14 C15 121.77(15) . . ?
C16 C15 C14 116.17(17) . . ?
C16 C15 C25 121.88(16) . . ?
C14 C15 C25 121.96(15) . . ?
C15 C16 C17 124.14(16) . . ?
C15 C16 H16 117.9 . . ?
C17 C16 H16 117.9 . . ?
C18 C17 C16 116.76(15) . . ?
C18 C17 C21 121.18(16) . . ?
C16 C17 C21 121.95(15) . . ?
C17 C18 C19 122.06(17) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C14 119.09(16) . . ?
C18 C19 C20 120.25(17) . . ?
C14 C19 C20 120.63(15) . . ?
N1 C20 C19 113.29(16) . . ?
N1 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C24 C21 C17 113.29(15) . . ?
C24 C21 C22 107.22(15) . . ?
C17 C21 C22 110.77(15) . . ?
C24 C21 C23 108.58(16) . . ?
C17 C21 C23 107.68(14) . . ?
C22 C21 C23 109.24(17) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 C28 111.81(14) . . ?
C15 C25 C26 109.85(14) . . ?
C28 C25 C26 107.76(14) . . ?
C15 C25 C27 111.08(14) . . ?
C28 C25 C27 106.79(14) . . ?
C26 C25 C27 109.43(14) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045

