# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_mo_180521d_0m
_database_code_depnum_ccdc_archive 'CCDC 1858686'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7693(13)
_cell_length_b                   12.582(2)
_cell_length_c                   15.723(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1537.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5058
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.11
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.9167.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16807
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.750
_diffrn_reflns_theta_min         2.073
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                4016
_reflns_number_total             5076
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.047
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1906(2) 0.03404(16) 0.79303(11) 0.0388(4) Uani 1 1 d . . . . .
C2 C 0.2741(2) 0.08332(14) 0.87192(9) 0.0327(3) Uani 1 1 d . . . . .
C3 C 0.3282(2) 0.02154(15) 0.93932(10) 0.0357(4) Uani 1 1 d . . . . .
C4 C 0.3028(3) -0.09786(17) 0.94235(13) 0.0455(4) Uani 1 1 d . . . . .
H4 H 0.197094 -0.110552 0.974813 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2742(3) -0.14456(18) 0.85502(15) 0.0559(5) Uani 1 1 d . . . . .
H5A H 0.239226 -0.218282 0.860141 0.067 Uiso 1 1 calc R . . . .
H5B H 0.380597 -0.142114 0.822769 0.067 Uiso 1 1 calc R . . . .
C6 C 0.1365(3) -0.08215(17) 0.80921(15) 0.0528(5) Uani 1 1 d . . . . .
H6A H 0.031846 -0.082933 0.842884 0.063 Uiso 1 1 calc R . . . .
H6B H 0.111696 -0.116192 0.755226 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3013(2) 0.19594(14) 0.87420(9) 0.0329(3) Uani 1 1 d . . . . .
C8 C 0.3787(2) 0.24280(15) 0.94718(10) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.4314(3) 0.17666(17) 1.01387(10) 0.0431(4) Uani 1 1 d . . . . .
H9 H 0.484007 0.206251 1.061445 0.052 Uiso 1 1 calc R . . . .
C10 C 0.4072(3) 0.07108(17) 1.01009(11) 0.0426(4) Uani 1 1 d . . . . .
H10 H 0.443528 0.029195 1.055405 0.051 Uiso 1 1 calc R . . . .
C11 C 0.2523(3) 0.26629(16) 0.80807(11) 0.0406(4) Uani 1 1 d . . . . .
H11 H 0.203981 0.238573 0.758708 0.049 Uiso 1 1 calc R . . . .
C12 C 0.2740(3) 0.37312(17) 0.81481(13) 0.0495(5) Uani 1 1 d . . . . .
H12 H 0.240059 0.417030 0.770293 0.059 Uiso 1 1 calc R . . . .
C13 C 0.3468(3) 0.41784(18) 0.88778(14) 0.0518(5) Uani 1 1 d . . . . .
H13 H 0.358413 0.491182 0.892395 0.062 Uiso 1 1 calc R . . . .
C14 C 0.4002(3) 0.35394(17) 0.95156(12) 0.0471(5) Uani 1 1 d . . . . .
H14 H 0.452026 0.383777 0.999222 0.056 Uiso 1 1 calc R . . . .
C15 C 0.0219(2) 0.08707(15) 0.76885(10) 0.0372(4) Uani 1 1 d . . . . .
C16 C -0.2460(3) 0.14501(18) 0.82401(14) 0.0512(5) Uani 1 1 d . . . . .
H16A H -0.243740 0.219454 0.810693 0.077 Uiso 1 1 calc GR . . . .
H16B H -0.312125 0.133899 0.874819 0.077 Uiso 1 1 calc GR . . . .
H16C H -0.297534 0.106624 0.777797 0.077 Uiso 1 1 calc GR . . . .
C17 C 0.4477(3) -0.15791(19) 0.98860(14) 0.0542(5) Uani 1 1 d . . . . .
H17A H 0.450460 -0.135652 1.047650 0.065 Uiso 1 1 calc R . . . .
H17B H 0.422911 -0.233458 0.987390 0.065 Uiso 1 1 calc R . . . .
C18 C 0.6145(3) -0.1396(2) 0.95092(17) 0.0607(6) Uani 1 1 d . . . . .
C19 C 0.3165(3) 0.0379(2) 0.71783(13) 0.0571(6) Uani 1 1 d . . . . .
H19A H 0.346557 0.110383 0.706046 0.086 Uiso 1 1 calc GR . . . .
H19B H 0.263133 0.007046 0.668583 0.086 Uiso 1 1 calc GR . . . .
H19C H 0.418521 -0.001471 0.731824 0.086 Uiso 1 1 calc GR . . . .
N1 N 0.7449(4) -0.1266(3) 0.9221(2) 0.0995(10) Uani 1 1 d . . . . .
O1 O -0.07349(16) 0.10771(12) 0.83706(8) 0.0433(3) Uani 1 1 d . . . . .
O2 O -0.0273(2) 0.10250(14) 0.69770(8) 0.0530(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 1.531(2) . ?
C1 C6 1.542(3) . ?
C1 C15 1.519(3) . ?
C1 C19 1.535(3) . ?
C2 C3 1.380(2) . ?
C2 C7 1.433(3) . ?
C3 C4 1.516(3) . ?
C3 C10 1.416(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.510(3) . ?
C4 C17 1.538(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.510(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.423(2) . ?
C7 C11 1.418(2) . ?
C8 C9 1.400(3) . ?
C8 C14 1.410(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.343(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.359(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.351(3) . ?
C14 H14 0.9300 . ?
C15 O1 1.329(2) . ?
C15 O2 1.198(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 O1 1.435(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.443(4) . ?
C18 N1 1.122(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 111.46(16) . . ?
C2 C1 C19 109.96(15) . . ?
C15 C1 C2 112.98(14) . . ?
C15 C1 C6 102.83(15) . . ?
C15 C1 C19 110.08(16) . . ?
C19 C1 C6 109.30(18) . . ?
C3 C2 C1 121.54(16) . . ?
C3 C2 C7 119.53(14) . . ?
C7 C2 C1 118.89(15) . . ?
C2 C3 C4 122.87(16) . . ?
C2 C3 C10 119.19(17) . . ?
C10 C3 C4 117.91(16) . . ?
C3 C4 H4 106.7 . . ?
C3 C4 C17 113.97(17) . . ?
C5 C4 C3 112.09(17) . . ?
C5 C4 H4 106.7 . . ?
C5 C4 C17 110.25(18) . . ?
C17 C4 H4 106.7 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C4 C5 C6 109.60(18) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C1 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 C1 112.22(18) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C2 119.48(15) . . ?
C11 C7 C2 124.02(15) . . ?
C11 C7 C8 116.49(16) . . ?
C9 C8 C7 118.77(16) . . ?
C9 C8 C14 121.22(16) . . ?
C14 C8 C7 120.02(16) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.92(16) . . ?
C10 C9 H9 119.5 . . ?
C3 C10 H10 119.0 . . ?
C9 C10 C3 122.08(17) . . ?
C9 C10 H10 119.0 . . ?
C7 C11 H11 119.1 . . ?
C12 C11 C7 121.81(17) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.85(19) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C8 C14 H14 119.4 . . ?
C13 C14 C8 121.19(18) . . ?
C13 C14 H14 119.4 . . ?
O1 C15 C1 111.40(14) . . ?
O2 C15 C1 125.44(16) . . ?
O2 C15 O1 122.97(17) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
C4 C17 H17A 109.1 . . ?
C4 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C4 112.60(17) . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
N1 C18 C17 179.0(3) . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 O1 C16 117.98(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_180716M_0m
_database_code_depnum_ccdc_archive 'CCDC 1858689'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39

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/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                   10.271(2)
_cell_length_b                   18.417(4)
_cell_length_c                   10.492(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.416(3)
_cell_angle_gamma                90
_cell_volume                     1807.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3107
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      22.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19189
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.212
_diffrn_reflns_theta_max         30.869
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5653
_reflns_number_gt                3325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1008P)²+0.0025P] 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         5653
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1898
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.11122(16) 0.05974(9) 0.32878(15) 0.0381(3) Uani 1 1 d . . . . .
C2 C 1.16190(16) 0.05008(8) 0.22835(15) 0.0369(3) Uani 1 1 d . . . . .
H2 H 1.2467 0.0247 0.2503 0.044 Uiso 1 1 calc R U . . .
C3 C 1.08798(14) 0.07788(8) 0.09204(15) 0.0327(3) Uani 1 1 d . . . . .
C4 C 1.14051(15) 0.06668(8) -0.01035(16) 0.0368(3) Uani 1 1 d . . . . .
H4 H 1.2230 0.0394 0.0110 0.044 Uiso 1 1 calc R U . . .
C5 C 1.07228(16) 0.09522(9) -0.13958(16) 0.0376(3) Uani 1 1 d . . . . .
H5 H 1.1084 0.0868 -0.2062 0.045 Uiso 1 1 calc R U . . .
C6 C 0.94679(15) 0.13773(8) -0.17628(15) 0.0344(3) Uani 1 1 d . . . . .
C7 C 0.88715(14) 0.14664(8) -0.08119(14) 0.0322(3) Uani 1 1 d . . . . .
C8 C 0.95820(14) 0.11634(8) 0.05705(14) 0.0313(3) Uani 1 1 d . . . . .
C9 C 0.90675(16) 0.12241(9) 0.16253(15) 0.0375(3) Uani 1 1 d . . . . .
H9 H 0.8196 0.1453 0.1416 0.045 Uiso 1 1 calc R U . . .
C10 C 0.98101(17) 0.09568(9) 0.29356(16) 0.0403(4) Uani 1 1 d . . . . .
H10 H 0.9447 0.1014 0.3608 0.048 Uiso 1 1 calc R U . . .
C11 C 0.74616(15) 0.18733(9) -0.11947(16) 0.0386(3) Uani 1 1 d . . . . .
C12 C 0.67369(18) 0.20417(12) -0.27835(19) 0.0562(5) Uani 1 1 d . . . . .
H12A H 0.6285 0.1605 -0.3288 0.067 Uiso 1 1 calc R U . . .
H12B H 0.5998 0.2404 -0.2957 0.067 Uiso 1 1 calc R U . . .
C13 C 0.7795(2) 0.23157(12) -0.33239(19) 0.0561(5) Uani 1 1 d . . . . .
H13A H 0.8308 0.2730 -0.2776 0.067 Uiso 1 1 calc R U . . .
H13B H 0.7297 0.2468 -0.4291 0.067 Uiso 1 1 calc R U . . .
C14 C 0.88344(17) 0.17127(10) -0.32181(16) 0.0431(4) Uani 1 1 d . . . . .
H14 H 0.8285 0.1330 -0.3867 0.052 Uiso 1 1 calc R U . . .
C15 C 1.19310(19) 0.03477(10) 0.47508(17) 0.0471(4) Uani 1 1 d . . . . .
C16 C 1.3920(3) -0.03279(15) 0.6277(2) 0.0785(7) Uani 1 1 d . . . . .
H16A H 1.4436 0.0072 0.6850 0.118 Uiso 1 1 calc R U . . .
H16B H 1.4584 -0.0680 0.6223 0.118 Uiso 1 1 calc R U . . .
H16C H 1.3332 -0.0548 0.6682 0.118 Uiso 1 1 calc R U . . .
C17 C 0.64010(15) 0.13631(10) -0.09956(16) 0.0421(4) Uani 1 1 d . . . . .
C18 C 0.4356(3) 0.12590(16) -0.0559(4) 0.0990(10) Uani 1 1 d . . . . .
H18A H 0.3801 0.1049 -0.1459 0.149 Uiso 1 1 calc R U . . .
H18B H 0.3747 0.1549 -0.0272 0.149 Uiso 1 1 calc R U . . .
H18C H 0.4782 0.0879 0.0112 0.149 Uiso 1 1 calc R U . . .
C19 C 0.9967(2) 0.19747(10) -0.37133(17) 0.0494(4) Uani 1 1 d . . . . .
H19A H 1.0493 0.1558 -0.3816 0.059 Uiso 1 1 calc R U . . .
H19B H 0.9490 0.2200 -0.4626 0.059 Uiso 1 1 calc R U . . .
C20 C 1.0964(2) 0.24883(12) -0.2764(2) 0.0553(5) Uani 1 1 d . . . . .
C25 C 0.76895(18) 0.25927(10) -0.0390(2) 0.0498(4) Uani 1 1 d . . . . .
H25A H 0.6788 0.2836 -0.0655 0.075 Uiso 1 1 calc R U . . .
H25B H 0.8330 0.2896 -0.0609 0.075 Uiso 1 1 calc R U . . .
H25C H 0.8093 0.2496 0.0598 0.075 Uiso 1 1 calc R U . . .
N1 N 1.1761(2) 0.28902(12) -0.2018(2) 0.0821(6) Uani 1 1 d . . . . .
O1 O 1.30297(14) -0.00688(8) 0.48911(12) 0.0614(4) Uani 1 1 d . . . . .
O2 O 1.16509(18) 0.05103(10) 0.57134(14) 0.0799(5) Uani 1 1 d . . . . .
O3 O 0.63390(12) 0.07240(7) -0.12077(14) 0.0570(4) Uani 1 1 d . . . . .
O4 O 0.54617(13) 0.17086(8) -0.06462(16) 0.0637(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 1.366(2) . ?
C1 C10 1.398(2) . ?
C1 C15 1.486(2) . ?
C2 C3 1.409(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(2) . ?
C3 C8 1.4173(19) . ?
C4 C5 1.349(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(2) . ?
C6 C14 1.522(2) . ?
C7 C8 1.440(2) . ?
C7 C11 1.529(2) . ?
C8 C9 1.414(2) . ?
C9 C10 1.359(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C17 1.517(2) . ?
C11 C25 1.536(2) . ?
C11 C12 1.550(2) . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.534(2) . ?
C14 H14 0.9800 . ?
C15 O2 1.197(2) . ?
C15 O1 1.322(2) . ?
C16 O1 1.442(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.195(2) . ?
C17 O4 1.3276(19) . ?
C18 O4 1.439(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.447(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N1 1.140(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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 C10 119.06(14) . . ?
C2 C1 C15 121.54(15) . . ?
C10 C1 C15 119.38(14) . . ?
C1 C2 C3 121.21(14) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 120.49(13) . . ?
C4 C3 C8 119.57(13) . . ?
C2 C3 C8 119.92(13) . . ?
C5 C4 C3 120.53(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.60(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 119.65(13) . . ?
C7 C6 C14 122.96(13) . . ?
C5 C6 C14 117.39(13) . . ?
C6 C7 C8 119.40(13) . . ?
C6 C7 C11 121.58(13) . . ?
C8 C7 C11 119.02(12) . . ?
C9 C8 C3 116.90(13) . . ?
C9 C8 C7 124.06(13) . . ?
C3 C8 C7 119.04(12) . . ?
C10 C9 C8 121.87(14) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C1 120.95(14) . . ?
C9 C10 H10 119.5 . . ?
C1 C10 H10 119.5 . . ?
C17 C11 C7 108.43(13) . . ?
C17 C11 C25 114.42(13) . . ?
C7 C11 C25 111.45(12) . . ?
C17 C11 C12 102.66(13) . . ?
C7 C11 C12 111.23(13) . . ?
C25 C11 C12 108.36(15) . . ?
C13 C12 C11 111.82(14) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 108.90(16) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C6 111.58(13) . . ?
C13 C14 C19 110.80(15) . . ?
C6 C14 C19 113.45(13) . . ?
C13 C14 H14 106.9 . . ?
C6 C14 H14 106.9 . . ?
C19 C14 H14 106.9 . . ?
O2 C15 O1 122.90(16) . . ?
O2 C15 C1 124.30(17) . . ?
O1 C15 C1 112.79(14) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 122.33(15) . . ?
O3 C17 C11 124.80(14) . . ?
O4 C17 C11 112.72(15) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C14 113.13(14) . . ?
C20 C19 H19A 109.0 . . ?
C14 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C14 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 C19 179.4(2) . . ?
C11 C25 H25A 109.5 . . ?
C11 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C11 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 O1 C16 117.42(15) . . ?
C17 O4 C18 115.12(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 2.3(2) . . . . ?
C15 C1 C2 C3 -176.01(14) . . . . ?
C1 C2 C3 C4 -179.18(15) . . . . ?
C1 C2 C3 C8 -0.3(2) . . . . ?
C2 C3 C4 C5 -177.90(15) . . . . ?
C8 C3 C4 C5 3.2(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -4.1(2) . . . . ?
C4 C5 C6 C14 176.27(15) . . . . ?
C5 C6 C7 C8 3.8(2) . . . . ?
C14 C6 C7 C8 -176.63(14) . . . . ?
C5 C6 C7 C11 -175.53(14) . . . . ?
C14 C6 C7 C11 4.0(2) . . . . ?
C4 C3 C8 C9 176.62(14) . . . . ?
C2 C3 C8 C9 -2.3(2) . . . . ?
C4 C3 C8 C7 -3.4(2) . . . . ?
C2 C3 C8 C7 177.69(13) . . . . ?
C6 C7 C8 C9 179.84(14) . . . . ?
C11 C7 C8 C9 -0.8(2) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C11 C7 C8 C3 179.25(13) . . . . ?
C3 C8 C9 C10 3.0(2) . . . . ?
C7 C8 C9 C10 -176.97(15) . . . . ?
C8 C9 C10 C1 -1.1(2) . . . . ?
C2 C1 C10 C9 -1.6(2) . . . . ?
C15 C1 C10 C9 176.73(15) . . . . ?
C6 C7 C11 C17 121.24(15) . . . . ?
C8 C7 C11 C17 -58.10(17) . . . . ?
C6 C7 C11 C25 -111.96(16) . . . . ?
C8 C7 C11 C25 68.70(18) . . . . ?
C6 C7 C11 C12 9.1(2) . . . . ?
C8 C7 C11 C12 -170.26(14) . . . . ?
C17 C11 C12 C13 -159.64(16) . . . . ?
C7 C11 C12 C13 -43.9(2) . . . . ?
C25 C11 C12 C13 78.96(19) . . . . ?
C11 C12 C13 C14 66.0(2) . . . . ?
C12 C13 C14 C6 -50.7(2) . . . . ?
C12 C13 C14 C19 -178.13(14) . . . . ?
C7 C6 C14 C13 17.2(2) . . . . ?
C5 C6 C14 C13 -163.25(15) . . . . ?
C7 C6 C14 C19 143.19(16) . . . . ?
C5 C6 C14 C19 -37.2(2) . . . . ?
C2 C1 C15 O2 168.41(19) . . . . ?
C10 C1 C15 O2 -9.9(3) . . . . ?
C2 C1 C15 O1 -10.6(2) . . . . ?
C10 C1 C15 O1 171.14(15) . . . . ?
C7 C11 C17 O3 -34.4(2) . . . . ?
C25 C11 C17 O3 -159.51(16) . . . . ?
C12 C11 C17 O3 83.3(2) . . . . ?
C7 C11 C17 O4 149.95(14) . . . . ?
C25 C11 C17 O4 24.89(19) . . . . ?
C12 C11 C17 O4 -92.28(16) . . . . ?
C13 C14 C19 C20 70.2(2) . . . . ?
C6 C14 C19 C20 -56.2(2) . . . . ?
O2 C15 O1 C16 -0.4(3) . . . . ?
C1 C15 O1 C16 178.57(17) . . . . ?
O3 C17 O4 C18 -0.7(3) . . . . ?
C11 C17 O4 C18 174.99(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665
C16 H16A O3 0.96 2.47 3.387(3) 158.7 1_656
C19 H19A O2 0.97 2.42 3.389(3) 174.9 1_554
C19 H19B O4 0.97 2.66 3.332(2) 126.9 4_665

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_180719F_0m
_database_code_depnum_ccdc_archive 'CCDC 1858687'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39

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                   8.712(3)
_cell_length_b                   23.551(7)
_cell_length_c                   9.110(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.515(5)
_cell_angle_gamma                90
_cell_volume                     1792.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2587
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      23.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12938
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3330
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0832P)²+0.3867P] 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         3330
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4171(3) 0.48918(9) 0.6999(2) 0.0449(5) Uani 1 1 d . . . . .
C2 C 0.3247(3) 0.51208(9) 0.5665(2) 0.0437(5) Uani 1 1 d . . . . .
H2 H 0.3439 0.5492 0.5414 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2010(2) 0.48093(8) 0.4662(2) 0.0394(5) Uani 1 1 d . . . . .
C4 C 0.1041(3) 0.50527(8) 0.3298(2) 0.0435(5) Uani 1 1 d . . . . .
H4 H 0.1227 0.5424 0.3047 0.052 Uiso 1 1 calc R U . . .
C5 C -0.0152(3) 0.47517(9) 0.2359(2) 0.0444(5) Uani 1 1 d . . . . .
H5 H -0.0786 0.4922 0.1472 0.053 Uiso 1 1 calc R U . . .
C6 C -0.0469(2) 0.41832(8) 0.2682(2) 0.0403(5) Uani 1 1 d . . . . .
C7 C 0.0447(3) 0.39233(8) 0.3994(2) 0.0405(5) Uani 1 1 d . . . . .
C8 C 0.1700(3) 0.42425(8) 0.5030(2) 0.0416(5) Uani 1 1 d . . . . .
C9 C 0.2685(3) 0.40196(9) 0.6424(2) 0.0521(6) Uani 1 1 d . . . . .
H9 H 0.2517 0.3650 0.6700 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3874(3) 0.43341(10) 0.7370(3) 0.0523(6) Uani 1 1 d . . . . .
H10 H 0.4498 0.4175 0.8279 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0078(3) 0.33158(9) 0.4394(3) 0.0490(6) Uani 1 1 d . . . . .
C12 C -0.1031(3) 0.30087(9) 0.2996(3) 0.0587(6) Uani 1 1 d . . . . .
H12A H -0.0419 0.2902 0.2300 0.070 Uiso 1 1 calc R U . . .
H12B H -0.1435 0.2664 0.3334 0.070 Uiso 1 1 calc R U . . .
C13 C -0.2427(3) 0.33760(10) 0.2154(3) 0.0593(6) Uani 1 1 d . . . . .
H13A H -0.3028 0.3493 0.2850 0.071 Uiso 1 1 calc R U . . .
H13B H -0.3137 0.3160 0.1329 0.071 Uiso 1 1 calc R U . . .
C14 C -0.1827(3) 0.38944(9) 0.1508(2) 0.0464(5) Uani 1 1 d . . . . .
H14 H -0.2715 0.4165 0.1195 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5515(3) 0.51985(10) 0.8068(3) 0.0480(5) Uani 1 1 d . . . . .
C16 C 0.6806(3) 0.60810(12) 0.8705(3) 0.0703(7) Uani 1 1 d . . . . .
H16A H 0.6730 0.6080 0.9736 0.105 Uiso 1 1 calc R U . . .
H16B H 0.6729 0.6464 0.8331 0.105 Uiso 1 1 calc R U . . .
H16C H 0.7814 0.5921 0.8686 0.105 Uiso 1 1 calc R U . . .
C17 C 0.1534(3) 0.29304(9) 0.4825(3) 0.0538(6) Uani 1 1 d . . . . .
C18 C 0.3958(4) 0.26848(13) 0.4302(3) 0.0804(9) Uani 1 1 d . . . . .
H18A H 0.4541 0.2682 0.5369 0.121 Uiso 1 1 calc R U . . .
H18B H 0.4641 0.2819 0.3714 0.121 Uiso 1 1 calc R U . . .
H18C H 0.3602 0.2307 0.3983 0.121 Uiso 1 1 calc R U . . .
C19 C -0.1276(3) 0.37503(10) 0.0086(3) 0.0538(6) Uani 1 1 d . . . . .
H19A H -0.0959 0.4097 -0.0321 0.065 Uiso 1 1 calc R U . . .
H19B H -0.0347 0.3504 0.0388 0.065 Uiso 1 1 calc R U . . .
C20 C -0.2521(3) 0.34718(11) -0.1106(3) 0.0624(7) Uani 1 1 d . . . . .
C21 C -0.0736(4) 0.33257(11) 0.5686(3) 0.0696(8) Uani 1 1 d . . . . .
H21A H -0.1059 0.2948 0.5860 0.104 Uiso 1 1 calc R U . . .
H21B H -0.1660 0.3568 0.5398 0.104 Uiso 1 1 calc R U . . .
H21C H 0.0003 0.3467 0.6606 0.104 Uiso 1 1 calc R U . . .
N1 N -0.3496(3) 0.32396(12) -0.2001(3) 0.0886(8) Uani 1 1 d . . . . .
O1 O 0.55276(18) 0.57496(7) 0.77517(19) 0.0602(5) Uani 1 1 d . . . . .
O2 O 0.6486(2) 0.49791(8) 0.9108(2) 0.0768(6) Uani 1 1 d . . . . .
O3 O 0.1673(3) 0.25294(7) 0.5664(2) 0.0803(6) Uani 1 1 d . . . . .
O4 O 0.2584(2) 0.30568(6) 0.40620(18) 0.0582(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
C1 C2 1.364(3) . ?
C1 C10 1.399(3) . ?
C1 C15 1.481(3) . ?
C2 C3 1.405(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(3) . ?
C3 C8 1.421(3) . ?
C4 C5 1.345(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 C14 1.512(3) . ?
C7 C8 1.436(3) . ?
C7 C11 1.533(3) . ?
C8 C9 1.416(3) . ?
C9 C10 1.363(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C17 1.517(3) . ?
C11 C21 1.537(3) . ?
C11 C12 1.543(3) . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.541(3) . ?
C14 H14 0.9800 . ?
C15 O2 1.193(3) . ?
C15 O1 1.330(3) . ?
C16 O1 1.433(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.200(3) . ?
C17 O4 1.330(3) . ?
C18 O4 1.449(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.455(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N1 1.136(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 C10 118.9(2) . . ?
C2 C1 C15 123.3(2) . . ?
C10 C1 C15 117.7(2) . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 121.16(19) . . ?
C2 C3 C8 119.93(19) . . ?
C4 C3 C8 118.91(19) . . ?
C5 C4 C3 120.48(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.84(19) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 120.12(19) . . ?
C7 C6 C14 123.88(18) . . ?
C5 C6 C14 116.00(18) . . ?
C6 C7 C8 118.84(18) . . ?
C6 C7 C11 120.82(19) . . ?
C8 C7 C11 120.25(18) . . ?
C9 C8 C3 116.9(2) . . ?
C9 C8 C7 123.31(19) . . ?
C3 C8 C7 119.78(18) . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C1 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C1 C10 H10 119.4 . . ?
C17 C11 C7 113.79(19) . . ?
C17 C11 C21 110.2(2) . . ?
C7 C11 C21 109.97(18) . . ?
C17 C11 C12 102.38(18) . . ?
C7 C11 C12 111.43(18) . . ?
C21 C11 C12 108.8(2) . . ?
C13 C12 C11 112.06(19) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 110.02(19) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C6 112.06(18) . . ?
C13 C14 C19 111.97(19) . . ?
C6 C14 C19 108.99(17) . . ?
C13 C14 H14 107.9 . . ?
C6 C14 H14 107.9 . . ?
C19 C14 H14 107.9 . . ?
O2 C15 O1 123.1(2) . . ?
O2 C15 C1 124.1(2) . . ?
O1 C15 C1 112.79(19) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 123.3(2) . . ?
O3 C17 C11 124.1(2) . . ?
O4 C17 C11 112.31(18) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C14 112.5(2) . . ?
C20 C19 H19A 109.1 . . ?
C14 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C14 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 C19 177.5(3) . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 O1 C16 116.95(19) . . ?
C17 O4 C18 116.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.1(3) . . . . ?
C15 C1 C2 C3 178.23(18) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C1 C2 C3 C8 0.0(3) . . . . ?
C2 C3 C4 C5 -179.14(19) . . . . ?
C8 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C14 -178.89(19) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C14 C6 C7 C8 -179.62(18) . . . . ?
C5 C6 C7 C11 177.54(18) . . . . ?
C14 C6 C7 C11 -3.2(3) . . . . ?
C2 C3 C8 C9 -0.1(3) . . . . ?
C4 C3 C8 C9 -178.87(19) . . . . ?
C2 C3 C8 C7 -179.32(18) . . . . ?
C4 C3 C8 C7 1.9(3) . . . . ?
C6 C7 C8 C9 178.6(2) . . . . ?
C11 C7 C8 C9 2.1(3) . . . . ?
C6 C7 C8 C3 -2.2(3) . . . . ?
C11 C7 C8 C3 -178.70(18) . . . . ?
C3 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C10 C1 -0.1(3) . . . . ?
C2 C1 C10 C9 0.1(3) . . . . ?
C15 C1 C10 C9 -178.3(2) . . . . ?
C6 C7 C11 C17 131.3(2) . . . . ?
C8 C7 C11 C17 -52.3(3) . . . . ?
C6 C7 C11 C21 -104.6(2) . . . . ?
C8 C7 C11 C21 71.8(3) . . . . ?
C6 C7 C11 C12 16.2(3) . . . . ?
C8 C7 C11 C12 -167.44(19) . . . . ?
C17 C11 C12 C13 -168.0(2) . . . . ?
C7 C11 C12 C13 -46.0(3) . . . . ?
C21 C11 C12 C13 75.4(2) . . . . ?
C11 C12 C13 C14 63.4(3) . . . . ?
C12 C13 C14 C6 -47.8(3) . . . . ?
C12 C13 C14 C19 75.0(3) . . . . ?
C7 C6 C14 C13 19.1(3) . . . . ?
C5 C6 C14 C13 -161.55(19) . . . . ?
C7 C6 C14 C19 -105.4(2) . . . . ?
C5 C6 C14 C19 74.0(2) . . . . ?
C2 C1 C15 O2 -167.8(2) . . . . ?
C10 C1 C15 O2 10.5(3) . . . . ?
C2 C1 C15 O1 12.4(3) . . . . ?
C10 C1 C15 O1 -169.30(19) . . . . ?
C7 C11 C17 O3 152.2(2) . . . . ?
C21 C11 C17 O3 28.2(3) . . . . ?
C12 C11 C17 O3 -87.4(3) . . . . ?
C7 C11 C17 O4 -33.2(3) . . . . ?
C21 C11 C17 O4 -157.3(2) . . . . ?
C12 C11 C17 O4 87.1(2) . . . . ?
C13 C14 C19 C20 55.7(3) . . . . ?
C6 C14 C19 C20 -179.80(19) . . . . ?
O2 C15 O1 C16 1.5(3) . . . . ?
C1 C15 O1 C16 -178.68(19) . . . . ?
O3 C17 O4 C18 -0.7(4) . . . . ?
C11 C17 O4 C18 -175.3(2) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.039

