# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_d19458
_database_code_depnum_ccdc_archive 'CCDC 1853703'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.34

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2744(3)
_cell_length_b                   14.5625(9)
_cell_length_c                   15.6489(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1429.85(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1968
_cell_measurement_theta_min      2.798
_cell_measurement_theta_max      23.848

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8485
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2509
_reflns_number_gt                1938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0419P)²+0.0128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         2509
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5852(3) 0.40345(15) 0.56706(14) 0.0273(5) Uani 1 1 d . . .
C2 C 0.7742(3) 0.35534(16) 0.56399(15) 0.0315(6) Uani 1 1 d . . .
H2 H 0.8564 0.3448 0.6140 0.038 Uiso 1 1 calc R . .
C3 C 0.8398(4) 0.32272(16) 0.48439(16) 0.0346(6) Uani 1 1 d . . .
H3 H 0.9681 0.2884 0.4800 0.042 Uiso 1 1 calc R . .
C4 C 0.7199(4) 0.33981(17) 0.41172(15) 0.0372(6) Uani 1 1 d . . .
H4 H 0.7680 0.3175 0.3580 0.045 Uiso 1 1 calc R . .
C5 C 0.5302(4) 0.38912(16) 0.41617(15) 0.0347(6) Uani 1 1 d . . .
H5 H 0.4486 0.4011 0.3663 0.042 Uiso 1 1 calc R . .
C6 C 0.4639(3) 0.42012(15) 0.49517(14) 0.0273(5) Uani 1 1 d . . .
C7 C 0.2753(4) 0.47505(16) 0.52455(15) 0.0315(6) Uani 1 1 d . . .
H7 H 0.1430 0.4601 0.4917 0.038 Uiso 1 1 calc R . .
C8 C 0.3234(3) 0.57877(17) 0.52542(15) 0.0302(6) Uani 1 1 d . . .
H8 H 0.2037 0.6125 0.5536 0.036 Uiso 1 1 calc R . .
C9 C 0.3755(4) 0.62309(16) 0.44137(16) 0.0311(6) Uani 1 1 d . . .
C10 C 0.2554(4) 0.63017(17) 0.36714(16) 0.0398(7) Uani 1 1 d . . .
H10 H 0.1155 0.6054 0.3646 0.048 Uiso 1 1 calc R . .
C11 C 0.3429(5) 0.67395(18) 0.29683(18) 0.0474(7) Uani 1 1 d . . .
H11 H 0.2638 0.6778 0.2452 0.057 Uiso 1 1 calc R . .
C12 C 0.5442(5) 0.71209(18) 0.30121(16) 0.0447(7) Uani 1 1 d . . .
H12 H 0.6009 0.7426 0.2526 0.054 Uiso 1 1 calc R . .
C13 C 0.6657(4) 0.70659(18) 0.37575(16) 0.0380(6) Uani 1 1 d . . .
H13 H 0.8035 0.7334 0.3786 0.046 Uiso 1 1 calc R . .
C14 C 0.5800(4) 0.66090(16) 0.44547(15) 0.0304(6) Uani 1 1 d . . .
C15 C 0.6689(4) 0.64002(16) 0.52980(15) 0.0299(6) Uani 1 1 d . . .
H15 H 0.8067 0.6576 0.5489 0.036 Uiso 1 1 calc R . .
C16 C 0.5278(3) 0.59253(15) 0.57601(14) 0.0274(5) Uani 1 1 d . . .
C17 C 0.5541(4) 0.54067(17) 0.65878(14) 0.0308(6) Uani 1 1 d . . .
C18 C 0.7849(3) 0.53775(18) 0.68971(15) 0.0362(6) Uani 1 1 d . . .
H18A H 0.7954 0.4975 0.7397 0.054 Uiso 1 1 calc R . .
H18B H 0.8310 0.5998 0.7053 0.054 Uiso 1 1 calc R . .
H18C H 0.8763 0.5141 0.6440 0.054 Uiso 1 1 calc R . .
C19 C 0.4112(4) 0.57875(19) 0.72973(15) 0.0407(7) Uani 1 1 d . . .
H19A H 0.4520 0.6423 0.7421 0.061 Uiso 1 1 calc R . .
H19B H 0.4281 0.5414 0.7814 0.061 Uiso 1 1 calc R . .
H19C H 0.2622 0.5769 0.7111 0.061 Uiso 1 1 calc R . .
N1 N 0.4842(3) 0.44175(14) 0.64295(11) 0.0310(5) Uani 1 1 d . . .
O1 O 0.2612(2) 0.44730(11) 0.61317(10) 0.0349(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(3) . ?
C1 C6 1.380(3) . ?
C1 N1 1.457(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.501(3) . ?
C7 O1 1.447(3) . ?
C7 C8 1.540(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.501(3) . ?
C8 C16 1.520(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.389(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.465(3) . ?
C15 C16 1.336(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.508(3) . ?
C17 N1 1.526(3) . ?
C17 C18 1.527(3) . ?
C17 C19 1.531(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 . ?
N1 O1 1.477(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.4(2) . . ?
C2 C1 N1 126.7(2) . . ?
C6 C1 N1 110.91(18) . . ?
C1 C2 C3 117.3(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 C7 106.20(18) . . ?
C5 C6 C7 133.3(2) . . ?
O1 C7 C6 101.12(18) . . ?
O1 C7 C8 106.10(18) . . ?
C6 C7 C8 111.76(18) . . ?
O1 C7 H7 112.4 . . ?
C6 C7 H7 112.4 . . ?
C8 C7 H7 112.4 . . ?
C9 C8 C16 102.46(18) . . ?
C9 C8 C7 117.2(2) . . ?
C16 C8 C7 107.41(19) . . ?
C9 C8 H8 109.8 . . ?
C16 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
C10 C9 C14 120.5(2) . . ?
C10 C9 C8 130.3(2) . . ?
C14 C9 C8 109.2(2) . . ?
C11 C10 C9 118.9(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 C15 131.4(2) . . ?
C9 C14 C15 108.0(2) . . ?
C16 C15 C14 110.04(19) . . ?
C16 C15 H15 125.0 . . ?
C14 C15 H15 125.0 . . ?
C15 C16 C17 130.6(2) . . ?
C15 C16 C8 110.2(2) . . ?
C17 C16 C8 118.3(2) . . ?
C16 C17 N1 107.56(17) . . ?
C16 C17 C18 112.9(2) . . ?
N1 C17 C18 107.32(19) . . ?
C16 C17 C19 112.2(2) . . ?
N1 C17 C19 106.94(19) . . ?
C18 C17 C19 109.59(19) . . ?
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 . . ?
C1 N1 O1 100.14(15) . . ?
C1 N1 C17 111.62(17) . . ?
O1 N1 C17 105.77(17) . . ?
C7 O1 N1 105.06(14) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_d19432
_database_code_depnum_ccdc_archive 'CCDC 1853704'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O2'
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.51

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.9831(15)
_cell_length_b                   13.3250(11)
_cell_length_c                   16.5868(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.177(2)
_cell_angle_gamma                90.00
_cell_volume                     4499.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.468
_cell_measurement_theta_max      24.181

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            59880
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.03
_reflns_number_total             7906
_reflns_number_gt                6042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1668P)²+3.2724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7906
_refine_ls_number_parameters     578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2619
_refine_ls_wR_factor_gt          0.2224
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0269(2) 0.6106(4) 0.1783(3) 0.0368(11) Uani 1 1 d . . .
H1 H 0.0135 0.5688 0.1915 0.044 Uiso 1 1 calc R . .
C2 C -0.0612(3) 0.5867(4) 0.2397(4) 0.0385(12) Uani 1 1 d . . .
C3 C -0.0391(3) 0.5611(4) 0.3264(4) 0.0457(13) Uani 1 1 d . . .
H3 H 0.0065 0.5547 0.3607 0.055 Uiso 1 1 calc R . .
C4 C -0.0866(3) 0.5451(5) 0.3615(4) 0.0562(16) Uani 1 1 d . . .
H4 H -0.0733 0.5269 0.4211 0.067 Uiso 1 1 calc R . .
C5 C -0.1522(3) 0.5548(5) 0.3122(4) 0.0534(15) Uani 1 1 d . . .
H5 H -0.1833 0.5442 0.3385 0.064 Uiso 1 1 calc R . .
C6 C -0.1742(3) 0.5798(4) 0.2248(4) 0.0451(13) Uani 1 1 d . . .
H6 H -0.2197 0.5849 0.1901 0.054 Uiso 1 1 calc R . .
C7 C -0.1271(3) 0.5969(3) 0.1906(4) 0.0388(12) Uani 1 1 d . . .
C8 C -0.1395(2) 0.7315(4) 0.0842(4) 0.0379(12) Uani 1 1 d . . .
C9 C -0.1454(3) 0.7446(4) -0.0104(4) 0.0393(13) Uani 1 1 d . . .
H9A H -0.1048 0.7217 -0.0160 0.059 Uiso 1 1 calc R . .
H9B H -0.1526 0.8156 -0.0266 0.059 Uiso 1 1 calc R . .
H9C H -0.1825 0.7050 -0.0490 0.059 Uiso 1 1 calc R . .
C10 C -0.2044(2) 0.7665(4) 0.0877(4) 0.0412(12) Uani 1 1 d . . .
H10A H -0.2030 0.7592 0.1472 0.062 Uiso 1 1 calc R . .
H10B H -0.2404 0.7257 0.0479 0.062 Uiso 1 1 calc R . .
H10C H -0.2117 0.8371 0.0702 0.062 Uiso 1 1 calc R . .
C11 C -0.0770(2) 0.7872(3) 0.1474(3) 0.0319(11) Uani 1 1 d . . .
H11 H -0.0704 0.8451 0.1132 0.038 Uiso 1 1 calc R . .
C12 C -0.0748(2) 0.8320(3) 0.2324(3) 0.0312(11) Uani 1 1 d . . .
C13 C -0.1208(2) 0.8944(3) 0.2461(4) 0.0348(11) Uani 1 1 d . . .
H13 H -0.1606 0.9104 0.1991 0.042 Uiso 1 1 calc R . .
C14 C -0.1083(3) 0.9336(4) 0.3297(4) 0.0411(13) Uani 1 1 d . . .
C15 C -0.1588(3) 1.0007(5) 0.3430(5) 0.0565(16) Uani 1 1 d . . .
H15A H -0.1963 1.0085 0.2878 0.085 Uiso 1 1 calc R . .
H15B H -0.1393 1.0666 0.3635 0.085 Uiso 1 1 calc R . .
H15C H -0.1736 0.9707 0.3864 0.085 Uiso 1 1 calc R . .
C16 C -0.0504(2) 0.9110(4) 0.3969(3) 0.0401(12) Uani 1 1 d . . .
H16 H -0.0427 0.9363 0.4535 0.048 Uiso 1 1 calc R . .
C17 C -0.0031(2) 0.8522(4) 0.3841(3) 0.0373(12) Uani 1 1 d . . .
H17 H 0.0368 0.8375 0.4312 0.045 Uiso 1 1 calc R . .
C18 C -0.0148(2) 0.8145(4) 0.3004(3) 0.0320(10) Uani 1 1 d . . .
C19 C 0.0278(2) 0.7538(3) 0.2689(3) 0.0242(11) Uani 1 1 d . . .
C20 C -0.0113(2) 0.7248(4) 0.1760(3) 0.0323(11) Uani 1 1 d . . .
C21 C 0.0274(2) 0.7426(4) 0.1175(4) 0.0368(13) Uani 1 1 d . . .
H21A H 0.0001 0.7243 0.0574 0.055 Uiso 1 1 calc R . .
H21B H 0.0672 0.7013 0.1377 0.055 Uiso 1 1 calc R . .
H21C H 0.0395 0.8136 0.1198 0.055 Uiso 1 1 calc R . .
C22 C 0.1309(2) 0.7525(3) 0.3873(3) 0.0268(10) Uani 1 1 d . . .
C23 C 0.1488(2) 0.8531(4) 0.4079(4) 0.0401(12) Uani 1 1 d . . .
H23 H 0.1284 0.9033 0.3657 0.048 Uiso 1 1 calc R . .
C24 C 0.1939(3) 0.8808(4) 0.4857(4) 0.0506(14) Uani 1 1 d . . .
H24 H 0.2049 0.9496 0.4977 0.061 Uiso 1 1 calc R . .
C25 C 0.2240(3) 0.8082(5) 0.5480(4) 0.0601(17) Uani 1 1 d . . .
H25 H 0.2556 0.8284 0.6027 0.072 Uiso 1 1 calc R . .
C26 C 0.2094(3) 0.7087(5) 0.5329(4) 0.0573(16) Uani 1 1 d . . .
H26 H 0.2300 0.6600 0.5766 0.069 Uiso 1 1 calc R . .
C27 C 0.1624(2) 0.6796(4) 0.4498(3) 0.0398(12) Uani 1 1 d . . .
C28 C 0.1480(3) 0.5738(4) 0.4311(4) 0.0523(15) Uani 1 1 d . . .
H28 H 0.1207 0.5567 0.3731 0.063 Uiso 1 1 calc R . .
C29 C 0.4720(2) 0.3883(4) 0.8009(3) 0.0349(11) Uani 1 1 d . . .
H29 H 0.5116 0.4316 0.8285 0.042 Uiso 1 1 calc R . .
C30 C 0.4364(2) 0.4141(3) 0.7053(3) 0.0347(11) Uani 1 1 d . . .
C31 C 0.4570(3) 0.4448(4) 0.6408(4) 0.0454(13) Uani 1 1 d . . .
H31 H 0.5022 0.4548 0.6519 0.054 Uiso 1 1 calc R . .
C32 C 0.4083(3) 0.4611(4) 0.5575(4) 0.0522(14) Uani 1 1 d . . .
H32 H 0.4213 0.4810 0.5114 0.063 Uiso 1 1 calc R . .
C33 C 0.3433(3) 0.4493(4) 0.5411(4) 0.0515(15) Uani 1 1 d . . .
H33 H 0.3118 0.4617 0.4843 0.062 Uiso 1 1 calc R . .
C34 C 0.3227(3) 0.4192(4) 0.6069(4) 0.0434(13) Uani 1 1 d . . .
H34 H 0.2773 0.4118 0.5961 0.052 Uiso 1 1 calc R . .
C35 C 0.3701(2) 0.4002(3) 0.6883(3) 0.0345(11) Uani 1 1 d . . .
C36 C 0.3608(2) 0.2596(4) 0.7799(3) 0.0311(11) Uani 1 1 d . . .
C37 C 0.2970(2) 0.2255(4) 0.7121(4) 0.0456(14) Uani 1 1 d . . .
H37A H 0.2985 0.2337 0.6541 0.068 Uiso 1 1 calc R . .
H37B H 0.2610 0.2658 0.7161 0.068 Uiso 1 1 calc R . .
H37C H 0.2898 0.1546 0.7216 0.068 Uiso 1 1 calc R . .
C38 C 0.3591(3) 0.2454(5) 0.8700(4) 0.0440(14) Uani 1 1 d . . .
H38A H 0.4014 0.2655 0.9142 0.066 Uiso 1 1 calc R . .
H38B H 0.3507 0.1747 0.8783 0.066 Uiso 1 1 calc R . .
H38C H 0.3240 0.2869 0.8755 0.066 Uiso 1 1 calc R . .
C39 C 0.4259(2) 0.2085(3) 0.7789(3) 0.0307(10) Uani 1 1 d . . .
H39 H 0.4341 0.1493 0.8188 0.037 Uiso 1 1 calc R . .
C40 C 0.4285(2) 0.1682(3) 0.6944(3) 0.0288(10) Uani 1 1 d . . .
C41 C 0.3830(2) 0.1079(4) 0.6313(3) 0.0340(11) Uani 1 1 d . . .
H41 H 0.3424 0.0920 0.6363 0.041 Uiso 1 1 calc R . .
C42 C 0.3965(2) 0.0704(4) 0.5610(3) 0.0343(11) Uani 1 1 d . . .
C43 C 0.3473(3) 0.0068(4) 0.4917(4) 0.0500(14) Uani 1 1 d . . .
H43A H 0.3087 -0.0041 0.5065 0.075 Uiso 1 1 calc R . .
H43B H 0.3673 -0.0580 0.4882 0.075 Uiso 1 1 calc R . .
H43C H 0.3341 0.0411 0.4355 0.075 Uiso 1 1 calc R . .
C44 C 0.4561(2) 0.0961(3) 0.5547(3) 0.0344(11) Uani 1 1 d . . .
H44 H 0.4649 0.0734 0.5059 0.041 Uiso 1 1 calc R . .
C45 C 0.5024(2) 0.1532(3) 0.6168(3) 0.0323(10) Uani 1 1 d . . .
H45 H 0.5428 0.1692 0.6114 0.039 Uiso 1 1 calc R . .
C46 C 0.4891(2) 0.1876(3) 0.6884(3) 0.0297(10) Uani 1 1 d . . .
C47 C 0.5298(2) 0.2485(3) 0.7625(3) 0.0235(11) Uani 1 1 d . . .
C48 C 0.4893(2) 0.2756(4) 0.8171(3) 0.0308(10) Uani 1 1 d . . .
C49 C 0.5293(2) 0.2569(4) 0.9137(3) 0.0373(13) Uani 1 1 d . . .
H49A H 0.5028 0.2747 0.9477 0.056 Uiso 1 1 calc R . .
H49B H 0.5691 0.2982 0.9326 0.056 Uiso 1 1 calc R . .
H49C H 0.5415 0.1859 0.9227 0.056 Uiso 1 1 calc R . .
C50 C 0.6325(2) 0.2494(3) 0.7486(3) 0.0278(11) Uani 1 1 d . . .
C51 C 0.6523(2) 0.1489(4) 0.7576(4) 0.0386(11) Uani 1 1 d . . .
H51 H 0.6347 0.1028 0.7868 0.046 Uiso 1 1 calc R . .
C52 C 0.6973(3) 0.1173(5) 0.7243(4) 0.0513(14) Uani 1 1 d . . .
H52 H 0.7100 0.0488 0.7290 0.062 Uiso 1 1 calc R . .
C53 C 0.7237(3) 0.1837(6) 0.6846(5) 0.068(2) Uani 1 1 d . . .
H53 H 0.7544 0.1603 0.6610 0.081 Uiso 1 1 calc R . .
C54 C 0.7074(3) 0.2831(6) 0.6775(4) 0.0569(16) Uani 1 1 d . . .
H54 H 0.7273 0.3288 0.6508 0.068 Uiso 1 1 calc R . .
C55 C 0.6609(2) 0.3164(4) 0.7103(3) 0.0418(12) Uani 1 1 d . . .
C56 C 0.6446(3) 0.4247(4) 0.7085(4) 0.0522(15) Uani 1 1 d . . .
H56 H 0.6174 0.4456 0.7383 0.063 Uiso 1 1 calc R . .
N1 N -0.13791(19) 0.6200(3) 0.1008(3) 0.0377(10) Uani 1 1 d . . .
N2 N 0.08698(18) 0.7244(3) 0.3042(3) 0.0355(10) Uani 1 1 d . . .
N3 N 0.36048(18) 0.3730(3) 0.7671(3) 0.0387(10) Uani 1 1 d . . .
N4 N 0.58877(18) 0.2810(3) 0.7879(3) 0.0370(10) Uani 1 1 d . . .
O1 O -0.07683(16) 0.5838(3) 0.0950(2) 0.0401(9) Uani 1 1 d . . .
O2 O 0.1676(2) 0.5053(3) 0.4826(3) 0.0755(14) Uani 1 1 d . . .
O3 O 0.42161(16) 0.4113(3) 0.8340(2) 0.0393(8) Uani 1 1 d . . .
O4 O 0.6640(3) 0.4887(4) 0.6710(4) 0.0902(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.448(6) . ?
C1 C2 1.512(8) . ?
C1 C20 1.563(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.375(8) . ?
C2 C7 1.376(7) . ?
C3 C4 1.392(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(8) . ?
C6 H6 0.9500 . ?
C7 N1 1.450(7) . ?
C8 N1 1.509(7) . ?
C8 C10 1.523(7) . ?
C8 C9 1.536(8) . ?
C8 C11 1.566(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.515(7) . ?
C11 C20 1.577(6) . ?
C11 H11 1.0000 . ?
C12 C18 1.394(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.408(8) . ?
C13 H13 0.9500 . ?
C14 C16 1.373(8) . ?
C14 C15 1.505(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.381(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.474(7) . ?
C19 N2 1.271(6) . ?
C19 C20 1.505(6) . ?
C20 C21 1.531(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N2 1.402(6) . ?
C22 C27 1.399(7) . ?
C22 C23 1.402(7) . ?
C23 C24 1.348(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.365(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.430(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.452(8) . ?
C28 O2 1.212(7) . ?
C28 H28 0.9500 . ?
C29 O3 1.443(6) . ?
C29 C30 1.520(7) . ?
C29 C48 1.547(7) . ?
C29 H29 1.0000 . ?
C30 C31 1.372(8) . ?
C30 C35 1.389(7) . ?
C31 C32 1.409(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.357(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(7) . ?
C34 H34 0.9500 . ?
C35 N3 1.446(7) . ?
C36 C37 1.500(6) . ?
C36 N3 1.525(7) . ?
C36 C38 1.521(8) . ?
C36 C39 1.589(6) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.523(6) . ?
C39 C48 1.575(6) . ?
C39 H39 1.0000 . ?
C40 C46 1.396(6) . ?
C40 C41 1.396(6) . ?
C41 C42 1.400(7) . ?
C41 H41 0.9500 . ?
C42 C44 1.394(7) . ?
C42 C43 1.507(7) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.373(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.402(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.462(6) . ?
C47 N4 1.278(6) . ?
C47 C48 1.534(6) . ?
C48 C49 1.530(7) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C55 1.375(7) . ?
C50 C51 1.398(7) . ?
C50 N4 1.415(6) . ?
C51 C52 1.367(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.358(9) . ?
C52 H52 0.9500 . ?
C53 C54 1.366(10) . ?
C53 H53 0.9500 . ?
C54 C55 1.399(8) . ?
C54 H54 0.9500 . ?
C55 C56 1.485(8) . ?
C56 O4 1.223(7) . ?
C56 H56 0.9500 . ?
N1 O1 1.463(5) . ?
N3 O3 1.474(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 101.5(4) . . ?
O1 C1 C20 108.1(4) . . ?
C2 C1 C20 113.0(4) . . ?
O1 C1 H1 111.2 . . ?
C2 C1 H1 111.2 . . ?
C20 C1 H1 111.2 . . ?
C3 C2 C7 121.4(5) . . ?
C3 C2 C1 133.4(5) . . ?
C7 C2 C1 105.2(5) . . ?
C2 C3 C4 116.8(5) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 121.6(6) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 116.9(5) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C2 121.9(5) . . ?
C6 C7 N1 127.0(5) . . ?
C2 C7 N1 110.9(5) . . ?
N1 C8 C10 104.6(4) . . ?
N1 C8 C9 106.6(4) . . ?
C10 C8 C9 106.6(5) . . ?
N1 C8 C11 113.0(4) . . ?
C10 C8 C11 115.3(4) . . ?
C9 C8 C11 110.1(5) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 121.4(4) . . ?
C12 C11 C20 103.0(4) . . ?
C8 C11 C20 115.0(4) . . ?
C12 C11 H11 105.3 . . ?
C8 C11 H11 105.4 . . ?
C20 C11 H11 105.3 . . ?
C18 C12 C13 119.5(4) . . ?
C18 C12 C11 112.0(4) . . ?
C13 C12 C11 128.0(4) . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C16 C14 C13 119.8(5) . . ?
C16 C14 C15 121.3(5) . . ?
C13 C14 C15 118.9(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 121.3(5) . . ?
C14 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 119.2(5) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C12 C18 C17 120.2(4) . . ?
C12 C18 C19 109.8(4) . . ?
C17 C18 C19 130.0(4) . . ?
N2 C19 C18 133.1(5) . . ?
N2 C19 C20 118.8(4) . . ?
C18 C19 C20 108.1(4) . . ?
C19 C20 C21 111.7(4) . . ?
C19 C20 C1 105.7(4) . . ?
C21 C20 C1 110.3(4) . . ?
C19 C20 C11 106.0(4) . . ?
C21 C20 C11 113.1(4) . . ?
C1 C20 C11 109.7(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C27 120.4(4) . . ?
N2 C22 C23 121.4(5) . . ?
C27 C22 C23 117.9(5) . . ?
C24 C23 C22 122.2(5) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C23 C24 C25 119.5(5) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 121.9(6) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 118.3(6) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C22 C27 C26 120.1(5) . . ?
C22 C27 C28 120.6(5) . . ?
C26 C27 C28 119.3(5) . . ?
O2 C28 C27 126.2(6) . . ?
O2 C28 H28 116.9 . . ?
C27 C28 H28 116.9 . . ?
O3 C29 C30 100.5(4) . . ?
O3 C29 C48 108.3(4) . . ?
C30 C29 C48 113.3(4) . . ?
O3 C29 H29 111.4 . . ?
C30 C29 H29 111.4 . . ?
C48 C29 H29 111.4 . . ?
C31 C30 C35 120.8(5) . . ?
C31 C30 C29 133.6(5) . . ?
C35 C30 C29 105.6(4) . . ?
C30 C31 C32 117.2(5) . . ?
C30 C31 H31 121.4 . . ?
C32 C31 H31 121.4 . . ?
C33 C32 C31 122.1(6) . . ?
C33 C32 H32 119.0 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C34 120.4(5) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 118.1(5) . . ?
C35 C34 H34 121.0 . . ?
C33 C34 H34 121.0 . . ?
C34 C35 C30 121.3(5) . . ?
C34 C35 N3 128.0(5) . . ?
C30 C35 N3 110.5(4) . . ?
C37 C36 N3 104.0(4) . . ?
C37 C36 C38 109.6(5) . . ?
N3 C36 C38 105.0(4) . . ?
C37 C36 C39 116.9(4) . . ?
N3 C36 C39 112.4(4) . . ?
C38 C36 C39 108.2(4) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C48 103.6(4) . . ?
C40 C39 C36 120.5(4) . . ?
C48 C39 C36 114.6(4) . . ?
C40 C39 H39 105.7 . . ?
C48 C39 H39 105.7 . . ?
C36 C39 H39 105.7 . . ?
C46 C40 C41 119.1(4) . . ?
C46 C40 C39 111.6(4) . . ?
C41 C40 C39 128.8(4) . . ?
C40 C41 C42 120.8(5) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C44 C42 C41 118.4(4) . . ?
C44 C42 C43 120.3(5) . . ?
C41 C42 C43 121.3(5) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C42 122.1(4) . . ?
C45 C44 H44 118.9 . . ?
C42 C44 H44 118.9 . . ?
C44 C45 C46 118.9(4) . . ?
C44 C45 H45 120.5 . . ?
C46 C45 H45 120.5 . . ?
C40 C46 C45 120.5(4) . . ?
C40 C46 C47 109.9(4) . . ?
C45 C46 C47 129.5(4) . . ?
N4 C47 C46 133.5(5) . . ?
N4 C47 C48 117.9(4) . . ?
C46 C47 C48 108.6(4) . . ?
C49 C48 C47 110.4(3) . . ?
C49 C48 C29 110.2(4) . . ?
C47 C48 C29 106.6(4) . . ?
C49 C48 C39 113.5(4) . . ?
C47 C48 C39 104.6(4) . . ?
C29 C48 C39 111.1(3) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C55 C50 C51 119.6(5) . . ?
C55 C50 N4 121.7(4) . . ?
C51 C50 N4 118.3(4) . . ?
C52 C51 C50 119.6(5) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
C53 C52 C51 120.2(6) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C52 C53 C54 121.8(6) . . ?
C52 C53 H53 119.1 . . ?
C54 C53 H53 119.1 . . ?
C53 C54 C55 118.7(6) . . ?
C53 C54 H54 120.7 . . ?
C55 C54 H54 120.7 . . ?
C50 C55 C54 120.0(5) . . ?
C50 C55 C56 119.5(5) . . ?
C54 C55 C56 120.4(5) . . ?
O4 C56 C55 124.1(7) . . ?
O4 C56 H56 117.9 . . ?
C55 C56 H56 117.9 . . ?
C7 N1 O1 101.5(4) . . ?
C7 N1 C8 112.3(4) . . ?
O1 N1 C8 105.7(4) . . ?
C19 N2 C22 125.1(4) . . ?
C35 N3 O3 101.1(4) . . ?
C35 N3 C36 112.3(4) . . ?
O3 N3 C36 106.4(3) . . ?
C47 N4 C50 121.8(4) . . ?
C1 O1 N1 103.9(3) . . ?
C29 O3 N3 104.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.337
_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_mo_180134lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1853705'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 N2 O2'
_chemical_formula_weight         412.51

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                   7.5024(14)
_cell_length_b                   9.4863(17)
_cell_length_c                   15.949(3)
_cell_angle_alpha                93.783(5)
_cell_angle_beta                 95.871(5)
_cell_angle_gamma                109.707(5)
_cell_volume                     1056.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.5825
_cell_measurement_theta_max      26.3311

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8638
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24878
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.291
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4304
_reflns_number_gt                3712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.7975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 -0.17097(16) 0.22599(13) 0.22383(7) 0.0216(2) Uani 1 1 d . . . . .
H1 H -0.115(3) 0.160(2) 0.2346(13) 0.032 Uiso 1 1 d . U . . .
O2 O 0.00173(15) 0.93181(11) 0.17281(6) 0.0167(2) Uani 1 1 d . . . . .
N1 N 0.10230(17) 0.51619(14) 0.19553(8) 0.0162(3) Uani 1 1 d . . . . .
H1A H -0.0183 0.4891 0.2038 0.019 Uiso 1 1 calc R U . . .
N2 N 0.00469(18) 0.99864(14) 0.25853(8) 0.0160(3) Uani 1 1 d . . . . .
C1 C -0.1812(2) 0.23645(17) 0.13434(10) 0.0209(3) Uani 1 1 d . . . . .
H28 H -0.2444 0.3096 0.1200 0.025 Uiso 1 1 calc R U . . .
H29 H -0.2609 0.1371 0.1040 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0118(2) 0.28464(17) 0.10420(9) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.1528(2) 0.42448(16) 0.13738(9) 0.0152(3) Uani 1 1 d . . . . .
C4 C 0.2356(2) 0.65352(16) 0.24333(9) 0.0142(3) Uani 1 1 d . . . . .
H22 H 0.3677 0.6560 0.2366 0.017 Uiso 1 1 calc R U . . .
C5 C 0.2179(2) 0.80262(16) 0.21537(9) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.0084(2) 0.78265(16) 0.18457(9) 0.0144(3) Uani 1 1 d . . . . .
H19 H -0.0404 0.7132 0.1309 0.017 Uiso 1 1 calc R U . . .
C7 C -0.1255(2) 0.73675(17) 0.25028(9) 0.0143(3) Uani 1 1 d . . . . .
C8 C -0.1176(2) 0.87034(16) 0.29434(9) 0.0150(3) Uani 1 1 d . . . . .
C9 C -0.2183(2) 0.87334(18) 0.36186(10) 0.0182(3) Uani 1 1 d . . . . .
H10 H -0.2127 0.9658 0.3908 0.022 Uiso 1 1 calc R U . . .
C10 C -0.3282(2) 0.73546(18) 0.38578(9) 0.0188(3) Uani 1 1 d . . . . .
H2 H -0.3954 0.7333 0.4333 0.023 Uiso 1 1 calc R U . . .
C11 C 0.22051(19) 0.66338(16) 0.33647(9) 0.0137(3) Uani 1 1 d . . . . .
C12 C 0.1943(2) 0.54740(17) 0.38785(10) 0.0175(3) Uani 1 1 d . . . . .
H21 H 0.1656 0.4468 0.3636 0.021 Uiso 1 1 calc R U . . .
C13 C 0.2104(2) 0.57985(18) 0.47467(10) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.1911 0.5013 0.5105 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2548(2) 0.72757(18) 0.50933(9) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.2680 0.7498 0.5691 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2803(2) 0.84372(17) 0.45754(9) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.3132 0.9447 0.4821 0.020 Uiso 1 1 calc R U . . .
C16 C 0.25766(19) 0.81168(16) 0.36969(9) 0.0136(3) Uani 1 1 d . . . . .
C17 C 0.2894(2) 0.91573(16) 0.29911(9) 0.0137(3) Uani 1 1 d . . . . .
H20 H 0.4309 0.9631 0.3010 0.016 Uiso 1 1 calc R U . . .
C18 C 0.3358(2) 0.85225(17) 0.14257(9) 0.0184(3) Uani 1 1 d . . . . .
H7 H 0.2958 0.7704 0.0962 0.028 Uiso 1 1 calc R U . . .
H8 H 0.4716 0.8766 0.1629 0.028 Uiso 1 1 calc R U . . .
H9 H 0.3154 0.9414 0.1220 0.028 Uiso 1 1 calc R U . . .
C19 C -0.2401(2) 0.60017(17) 0.27232(9) 0.0162(3) Uani 1 1 d . . . . .
H12 H -0.2500 0.5081 0.2415 0.019 Uiso 1 1 calc R U . . .
C20 C -0.3409(2) 0.60127(18) 0.34099(10) 0.0184(3) Uani 1 1 d . . . . .
H11 H -0.4195 0.5085 0.3574 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2088(2) 1.04896(16) 0.30036(9) 0.0158(3) Uani 1 1 d . . . . .
C22 C 0.3265(2) 1.17377(17) 0.25163(10) 0.0203(3) Uani 1 1 d . . . . .
H14 H 0.3132 1.1351 0.1920 0.030 Uiso 1 1 calc R U . . .
H13 H 0.4612 1.2074 0.2760 0.030 Uiso 1 1 calc R U . . .
H15 H 0.2803 1.2588 0.2557 0.030 Uiso 1 1 calc R U . . .
C23 C 0.2091(2) 1.12037(17) 0.38899(10) 0.0197(3) Uani 1 1 d . . . . .
H18 H 0.1551 1.2007 0.3846 0.029 Uiso 1 1 calc R U . . .
H16 H 0.3405 1.1627 0.4178 0.029 Uiso 1 1 calc R U . . .
H17 H 0.1320 1.0436 0.4215 0.029 Uiso 1 1 calc R U . . .
C24 C 0.3322(2) 0.46294(17) 0.11013(9) 0.0178(3) Uani 1 1 d . . . . .
H24 H 0.4275 0.5574 0.1306 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3727(2) 0.36397(18) 0.05324(9) 0.0201(3) Uani 1 1 d . . . . .
H25 H 0.4972 0.3902 0.0369 0.024 Uiso 1 1 calc R U . . .
C26 C 0.2351(2) 0.22822(18) 0.02004(10) 0.0219(3) Uani 1 1 d . . . . .
H26 H 0.2628 0.1620 -0.0197 0.026 Uiso 1 1 calc R U . . .
C27 C 0.0556(2) 0.19068(17) 0.04596(10) 0.0204(3) Uani 1 1 d . . . . .
H27 H -0.0401 0.0978 0.0231 0.024 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 C1 1.433(2) . ?
O1 H1 0.88(2) . ?
O2 C6 1.4561(17) . ?
O2 N2 1.4634(15) . ?
N1 C3 1.3956(18) . ?
N1 C4 1.4537(18) . ?
N1 H1A 0.8800 . ?
N2 C8 1.4475(19) . ?
N2 C21 1.5081(19) . ?
C1 C2 1.504(2) . ?
C1 H28 0.9900 . ?
C1 H29 0.9900 . ?
C2 C27 1.385(2) . ?
C2 C3 1.416(2) . ?
C3 C24 1.394(2) . ?
C4 C11 1.501(2) . ?
C4 C5 1.554(2) . ?
C4 H22 1.0000 . ?
C5 C18 1.5344(19) . ?
C5 C6 1.542(2) . ?
C5 C17 1.5808(19) . ?
C6 C7 1.509(2) . ?
C6 H19 1.0000 . ?
C7 C19 1.383(2) . ?
C7 C8 1.388(2) . ?
C8 C9 1.381(2) . ?
C9 C10 1.393(2) . ?
C9 H10 0.9500 . ?
C10 C20 1.387(2) . ?
C10 H2 0.9500 . ?
C11 C12 1.388(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.382(2) . ?
C12 H21 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H4 0.9500 . ?
C14 C15 1.394(2) . ?
C14 H5 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H6 0.9500 . ?
C16 C17 1.530(2) . ?
C17 C21 1.574(2) . ?
C17 H20 1.0000 . ?
C18 H7 0.9800 . ?
C18 H8 0.9800 . ?
C18 H9 0.9800 . ?
C19 C20 1.394(2) . ?
C19 H12 0.9500 . ?
C20 H11 0.9500 . ?
C21 C23 1.526(2) . ?
C21 C22 1.530(2) . ?
C22 H14 0.9800 . ?
C22 H13 0.9800 . ?
C22 H15 0.9800 . ?
C23 H18 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C24 C25 1.391(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 H27 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
C1 O1 H1 106.9(13) . . ?
C6 O2 N2 104.33(10) . . ?
C3 N1 C4 124.38(12) . . ?
C3 N1 H1A 117.8 . . ?
C4 N1 H1A 117.8 . . ?
C8 N2 O2 101.07(10) . . ?
C8 N2 C21 112.08(11) . . ?
O2 N2 C21 106.61(10) . . ?
O1 C1 C2 112.87(12) . . ?
O1 C1 H28 109.0 . . ?
C2 C1 H28 109.0 . . ?
O1 C1 H29 109.0 . . ?
C2 C1 H29 109.0 . . ?
H28 C1 H29 107.8 . . ?
C27 C2 C3 119.31(14) . . ?
C27 C2 C1 120.40(14) . . ?
C3 C2 C1 120.25(13) . . ?
C24 C3 N1 123.91(13) . . ?
C24 C3 C2 118.61(13) . . ?
N1 C3 C2 117.48(13) . . ?
N1 C4 C11 113.90(12) . . ?
N1 C4 C5 115.53(12) . . ?
C11 C4 C5 104.34(11) . . ?
N1 C4 H22 107.6 . . ?
C11 C4 H22 107.6 . . ?
C5 C4 H22 107.6 . . ?
C18 C5 C6 108.36(12) . . ?
C18 C5 C4 109.89(11) . . ?
C6 C5 C4 111.13(11) . . ?
C18 C5 C17 114.16(12) . . ?
C6 C5 C17 109.32(11) . . ?
C4 C5 C17 103.96(11) . . ?
O2 C6 C7 100.70(11) . . ?
O2 C6 C5 107.10(11) . . ?
C7 C6 C5 114.59(12) . . ?
O2 C6 H19 111.3 . . ?
C7 C6 H19 111.3 . . ?
C5 C6 H19 111.3 . . ?
C19 C7 C8 120.06(13) . . ?
C19 C7 C6 134.38(13) . . ?
C8 C7 C6 105.55(12) . . ?
C9 C8 C7 122.39(14) . . ?
C9 C8 N2 126.99(13) . . ?
C7 C8 N2 110.62(12) . . ?
C8 C9 C10 117.35(14) . . ?
C8 C9 H10 121.3 . . ?
C10 C9 H10 121.3 . . ?
C20 C10 C9 120.79(14) . . ?
C20 C10 H2 119.6 . . ?
C9 C10 H2 119.6 . . ?
C12 C11 C16 121.87(14) . . ?
C12 C11 C4 126.63(13) . . ?
C16 C11 C4 111.15(12) . . ?
C13 C12 C11 119.29(14) . . ?
C13 C12 H21 120.4 . . ?
C11 C12 H21 120.4 . . ?
C12 C13 C14 119.76(14) . . ?
C12 C13 H4 120.1 . . ?
C14 C13 H4 120.1 . . ?
C13 C14 C15 120.80(14) . . ?
C13 C14 H5 119.6 . . ?
C15 C14 H5 119.6 . . ?
C14 C15 C16 119.97(14) . . ?
C14 C15 H6 120.0 . . ?
C16 C15 H6 120.0 . . ?
C11 C16 C15 118.18(13) . . ?
C11 C16 C17 110.35(12) . . ?
C15 C16 C17 131.04(13) . . ?
C16 C17 C21 119.98(12) . . ?
C16 C17 C5 103.37(11) . . ?
C21 C17 C5 114.14(11) . . ?
C16 C17 H20 106.1 . . ?
C21 C17 H20 106.1 . . ?
C5 C17 H20 106.1 . . ?
C5 C18 H7 109.5 . . ?
C5 C18 H8 109.5 . . ?
H7 C18 H8 109.5 . . ?
C5 C18 H9 109.5 . . ?
H7 C18 H9 109.5 . . ?
H8 C18 H9 109.5 . . ?
C7 C19 C20 118.21(14) . . ?
C7 C19 H12 120.9 . . ?
C20 C19 H12 120.9 . . ?
C10 C20 C19 121.14(14) . . ?
C10 C20 H11 119.4 . . ?
C19 C20 H11 119.4 . . ?
N2 C21 C23 105.73(12) . . ?
N2 C21 C22 107.10(12) . . ?
C23 C21 C22 107.45(12) . . ?
N2 C21 C17 111.83(11) . . ?
C23 C21 C17 114.30(12) . . ?
C22 C21 C17 110.06(12) . . ?
C21 C22 H14 109.5 . . ?
C21 C22 H13 109.5 . . ?
H14 C22 H13 109.5 . . ?
C21 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
H13 C22 H15 109.5 . . ?
C21 C23 H18 109.5 . . ?
C21 C23 H16 109.5 . . ?
H18 C23 H16 109.5 . . ?
C21 C23 H17 109.5 . . ?
H18 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C25 C24 C3 120.48(14) . . ?
C25 C24 H24 119.8 . . ?
C3 C24 H24 119.8 . . ?
C26 C25 C24 121.09(15) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 118.56(14) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C2 C27 C26 121.91(15) . . ?
C2 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

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

data_mo_180316lt_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1853706'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N2 O'
_chemical_formula_weight         393.49

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                   9.3848(5)
_cell_length_b                   17.3334(8)
_cell_length_c                   12.7967(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.091(2)
_cell_angle_gamma                90
_cell_volume                     2076.34(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5520
_cell_measurement_theta_min      2.1756
_cell_measurement_theta_max      25.2567

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9086
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            36450
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4257
_reflns_number_gt                3228
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+1.4719P] 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         4257
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.32880(13) 1.06694(7) 0.56100(10) 0.0182(3) Uani 1 1 d . . . . .
N1 N 0.14789(16) 0.93240(9) 0.58488(11) 0.0163(3) Uani 1 1 d . . . . .
H12 H 0.1629 0.9627 0.5316 0.020 Uiso 1 1 calc R U . . .
N2 N 0.64691(16) 0.91471(9) 0.66766(11) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.6864 0.8868 0.6200 0.019 Uiso 1 1 calc R U . . .
C1 C -0.1266(2) 0.75123(11) 0.62323(15) 0.0213(4) Uani 1 1 d . . . . .
H1 H -0.1854 0.7079 0.6347 0.026 Uiso 1 1 calc R U . . .
C2 C -0.0324(2) 0.77735(11) 0.70365(15) 0.0187(4) Uani 1 1 d . . . . .
H4 H -0.0281 0.7529 0.7702 0.022 Uiso 1 1 calc R U . . .
C3 C 0.05640(19) 0.84018(11) 0.68600(14) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.16814(19) 0.88058(10) 0.74587(14) 0.0155(4) Uani 1 1 d . . . . .
C5 C 0.22144(19) 0.93494(10) 0.68170(13) 0.0148(4) Uani 1 1 d . . . . .
C6 C 0.34689(19) 0.98604(10) 0.71282(13) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.42234(19) 1.01349(10) 0.61593(13) 0.0143(4) Uani 1 1 d . . . . .
H16 H 0.4347 0.9680 0.5695 0.017 Uiso 1 1 calc R U . . .
C8 C 0.56809(19) 1.04667(10) 0.64638(13) 0.0149(4) Uani 1 1 d . . . . .
C9 C 0.6778(2) 0.99442(10) 0.67594(13) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.8150(2) 1.02117(11) 0.70393(14) 0.0187(4) Uani 1 1 d . . . . .
H15 H 0.8893 0.9857 0.7234 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8432(2) 1.09956(12) 0.70347(15) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.9364 1.1178 0.7241 0.027 Uiso 1 1 calc R U . . .
C12 C -0.1367(2) 0.78761(12) 0.52533(15) 0.0224(4) Uani 1 1 d . . . . .
H3 H -0.2037 0.7692 0.4719 0.027 Uiso 1 1 calc R U . . .
C13 C -0.05088(19) 0.84977(11) 0.50508(15) 0.0196(4) Uani 1 1 d . . . . .
H25 H -0.0583 0.8747 0.4388 0.023 Uiso 1 1 calc R U . . .
C14 C 0.04680(19) 0.87469(11) 0.58493(14) 0.0166(4) Uani 1 1 d . . . . .
C15 C 0.2309(2) 0.87161(10) 0.85297(14) 0.0164(4) Uani 1 1 d . . . . .
C16 C 0.36742(19) 0.90338(10) 0.87633(13) 0.0145(4) Uani 1 1 d . . . . .
C17 C 0.45030(19) 0.93881(10) 0.78938(13) 0.0143(4) Uani 1 1 d . . . . .
H20 H 0.5172 0.9772 0.8245 0.017 Uiso 1 1 calc R U . . .
C18 C 0.54705(19) 0.87699(10) 0.73957(14) 0.0160(4) Uani 1 1 d . . . . .
C19 C 0.6413(2) 0.83815(12) 0.82709(15) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.7067 0.8019 0.7963 0.035 Uiso 1 1 calc R U . . .
H5 H 0.5809 0.8102 0.8737 0.035 Uiso 1 1 calc R U . . .
H7 H 0.6966 0.8775 0.8672 0.035 Uiso 1 1 calc R U . . .
C20 C 0.4667(2) 0.81447(11) 0.67508(15) 0.0212(4) Uani 1 1 d . . . . .
H9 H 0.4095 0.8384 0.6168 0.032 Uiso 1 1 calc R U . . .
H8 H 0.4038 0.7863 0.7197 0.032 Uiso 1 1 calc R U . . .
H10 H 0.5354 0.7786 0.6474 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7362(2) 1.15140(11) 0.67315(15) 0.0214(4) Uani 1 1 d . . . . .
H14 H 0.7566 1.2050 0.6714 0.026 Uiso 1 1 calc R U . . .
C22 C 0.5988(2) 1.12512(11) 0.64517(14) 0.0189(4) Uani 1 1 d . . . . .
H13 H 0.5254 1.1610 0.6251 0.023 Uiso 1 1 calc R U . . .
C23 C 0.2938(2) 1.05704(11) 0.77256(14) 0.0173(4) Uani 1 1 d . . . . .
H18 H 0.2238 1.0856 0.7271 0.026 Uiso 1 1 calc R U . . .
H19 H 0.3750 1.0907 0.7930 0.026 Uiso 1 1 calc R U . . .
H17 H 0.2490 1.0397 0.8354 0.026 Uiso 1 1 calc R U . . .
C24 C 0.4251(2) 0.90200(11) 0.97966(14) 0.0178(4) Uani 1 1 d . . . . .
H24 H 0.5154 0.9253 0.9968 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3532(2) 0.86719(12) 1.05791(15) 0.0230(4) Uani 1 1 d . . . . .
H23 H 0.3943 0.8667 1.1279 0.028 Uiso 1 1 calc R U . . .
C26 C 0.2217(2) 0.83324(12) 1.03406(15) 0.0251(5) Uani 1 1 d . . . . .
H21 H 0.1737 0.8077 1.0871 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1601(2) 0.83662(12) 0.93267(15) 0.0223(4) Uani 1 1 d . . . . .
H22 H 0.0682 0.8148 0.9171 0.027 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 C7 1.427(2) . ?
N1 C5 1.375(2) . ?
N1 C14 1.379(2) . ?
N1 H12 0.8800 . ?
N2 C9 1.414(2) . ?
N2 C18 1.509(2) . ?
N2 H11 0.8800 . ?
C1 C2 1.384(3) . ?
C1 C12 1.400(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(3) . ?
C2 H4 0.9500 . ?
C3 C14 1.422(3) . ?
C3 C4 1.436(3) . ?
C4 C5 1.368(2) . ?
C4 C15 1.461(3) . ?
C5 C6 1.504(3) . ?
C6 C7 1.546(2) . ?
C6 C23 1.550(2) . ?
C6 C17 1.561(2) . ?
C7 C8 1.509(3) . ?
C7 H16 1.0000 . ?
C8 C22 1.390(3) . ?
C8 C9 1.403(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.384(3) . ?
C10 H15 0.9500 . ?
C11 C21 1.382(3) . ?
C11 H2 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H3 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H25 0.9500 . ?
C15 C27 1.395(3) . ?
C15 C16 1.407(3) . ?
C16 C24 1.393(3) . ?
C16 C17 1.531(2) . ?
C17 C18 1.569(2) . ?
C17 H20 1.0000 . ?
C18 C20 1.528(3) . ?
C18 C19 1.533(3) . ?
C19 H6 0.9800 . ?
C19 H5 0.9800 . ?
C19 H7 0.9800 . ?
C20 H9 0.9800 . ?
C20 H8 0.9800 . ?
C20 H10 0.9800 . ?
C21 C22 1.390(3) . ?
C21 H14 0.9500 . ?
C22 H13 0.9500 . ?
C23 H18 0.9800 . ?
C23 H19 0.9800 . ?
C23 H17 0.9800 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H23 0.9500 . ?
C26 C27 1.383(3) . ?
C26 H21 0.9500 . ?
C27 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
C5 N1 C14 108.90(15) . . ?
C5 N1 H12 125.6 . . ?
C14 N1 H12 125.6 . . ?
C9 N2 C18 120.71(14) . . ?
C9 N2 H11 119.6 . . ?
C18 N2 H11 119.6 . . ?
C2 C1 C12 121.12(18) . . ?
C2 C1 H1 119.4 . . ?
C12 C1 H1 119.4 . . ?
C1 C2 C3 119.39(18) . . ?
C1 C2 H4 120.3 . . ?
C3 C2 H4 120.3 . . ?
C2 C3 C14 118.31(17) . . ?
C2 C3 C4 135.57(17) . . ?
C14 C3 C4 106.05(16) . . ?
C5 C4 C3 107.47(16) . . ?
C5 C4 C15 119.76(17) . . ?
C3 C4 C15 132.73(17) . . ?
C4 C5 N1 109.71(16) . . ?
C4 C5 C6 124.03(16) . . ?
N1 C5 C6 126.19(15) . . ?
C5 C6 C7 111.32(14) . . ?
C5 C6 C23 108.97(14) . . ?
C7 C6 C23 109.44(14) . . ?
C5 C6 C17 107.29(14) . . ?
C7 C6 C17 111.40(14) . . ?
C23 C6 C17 108.32(14) . . ?
O1 C7 C8 113.22(14) . . ?
O1 C7 C6 107.11(14) . . ?
C8 C7 C6 111.64(14) . . ?
O1 C7 H16 108.2 . . ?
C8 C7 H16 108.2 . . ?
C6 C7 H16 108.2 . . ?
C22 C8 C9 119.04(17) . . ?
C22 C8 C7 123.69(17) . . ?
C9 C8 C7 117.26(16) . . ?
C10 C9 C8 120.15(17) . . ?
C10 C9 N2 121.73(17) . . ?
C8 C9 N2 117.90(16) . . ?
C11 C10 C9 119.98(18) . . ?
C11 C10 H15 120.0 . . ?
C9 C10 H15 120.0 . . ?
C21 C11 C10 120.26(18) . . ?
C21 C11 H2 119.9 . . ?
C10 C11 H2 119.9 . . ?
C13 C12 C1 121.10(18) . . ?
C13 C12 H3 119.5 . . ?
C1 C12 H3 119.5 . . ?
C12 C13 C14 117.83(18) . . ?
C12 C13 H25 121.1 . . ?
C14 C13 H25 121.1 . . ?
N1 C14 C13 129.94(17) . . ?
N1 C14 C3 107.86(16) . . ?
C13 C14 C3 122.20(18) . . ?
C27 C15 C16 119.25(17) . . ?
C27 C15 C4 123.46(17) . . ?
C16 C15 C4 117.23(16) . . ?
C24 C16 C15 118.78(16) . . ?
C24 C16 C17 120.90(16) . . ?
C15 C16 C17 120.31(15) . . ?
C16 C17 C6 109.95(14) . . ?
C16 C17 C18 111.11(14) . . ?
C6 C17 C18 117.08(14) . . ?
C16 C17 H20 106.0 . . ?
C6 C17 H20 106.0 . . ?
C18 C17 H20 106.0 . . ?
N2 C18 C20 106.37(14) . . ?
N2 C18 C19 106.55(15) . . ?
C20 C18 C19 108.66(16) . . ?
N2 C18 C17 110.76(14) . . ?
C20 C18 C17 115.23(15) . . ?
C19 C18 C17 108.89(15) . . ?
C18 C19 H6 109.5 . . ?
C18 C19 H5 109.5 . . ?
H6 C19 H5 109.5 . . ?
C18 C19 H7 109.5 . . ?
H6 C19 H7 109.5 . . ?
H5 C19 H7 109.5 . . ?
C18 C20 H9 109.5 . . ?
C18 C20 H8 109.5 . . ?
H9 C20 H8 109.5 . . ?
C18 C20 H10 109.5 . . ?
H9 C20 H10 109.5 . . ?
H8 C20 H10 109.5 . . ?
C11 C21 C22 120.08(18) . . ?
C11 C21 H14 120.0 . . ?
C22 C21 H14 120.0 . . ?
C21 C22 C8 120.47(18) . . ?
C21 C22 H13 119.8 . . ?
C8 C22 H13 119.8 . . ?
C6 C23 H18 109.5 . . ?
C6 C23 H19 109.5 . . ?
H18 C23 H19 109.5 . . ?
C6 C23 H17 109.5 . . ?
H18 C23 H17 109.5 . . ?
H19 C23 H17 109.5 . . ?
C25 C24 C16 121.15(18) . . ?
C25 C24 H24 119.4 . . ?
C16 C24 H24 119.4 . . ?
C26 C25 C24 119.97(18) . . ?
C26 C25 H23 120.0 . . ?
C24 C25 H23 120.0 . . ?
C25 C26 C27 119.71(18) . . ?
C25 C26 H21 120.1 . . ?
C27 C26 H21 120.1 . . ?
C26 C27 C15 121.04(19) . . ?
C26 C27 H22 119.5 . . ?
C15 C27 H22 119.5 . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.050

_shelxl_version_number           2014/6



