# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b170615b_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1585807'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N4 O4'
_chemical_formula_weight         392.15

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   P2(1)/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                   10.5329(9)
_cell_length_b                   10.3187(8)
_cell_length_c                   18.4305(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.847(2)
_cell_angle_gamma                90.00
_cell_volume                     1984.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5342
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.70

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31003
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4564
_reflns_number_gt                2790
_reflns_threshold_expression     >2sigma(I)

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.2811
_refine_ls_wR_factor_gt          0.1819
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
O01 O 0.47214(18) 0.27736(18) 0.84685(10) 0.0285(5) Uani 1 1 d . . .
O02 O 0.85103(19) 0.3904(2) 0.77470(12) 0.0363(5) Uani 1 1 d . . .
O03 O 0.3541(2) 0.53924(18) 0.52076(10) 0.0315(5) Uani 1 1 d . . .
O04 O 0.8065(2) 0.2227(2) 0.92657(11) 0.0364(6) Uani 1 1 d . . .
H04 H 0.7657 0.1718 0.9505 0.055 Uiso 1 1 calc R . .
N01 N 0.4798(2) 0.5211(2) 0.62835(12) 0.0246(5) Uani 1 1 d . . .
H01 H 0.4991 0.6038 0.6254 0.029 Uiso 1 1 calc R . .
N02 N 0.6599(2) 0.3298(2) 0.80738(12) 0.0270(6) Uani 1 1 d . . .
H02 H 0.7003 0.2850 0.8441 0.032 Uiso 1 1 calc R . .
N03 N 0.2459(2) 0.3588(2) 0.67985(13) 0.0277(6) Uani 1 1 d . . .
N04 N 0.6681(2) 0.4541(2) 0.70207(12) 0.0260(5) Uani 1 1 d . . .
C18 C 0.5297(3) 0.3312(2) 0.80103(14) 0.0230(6) Uani 1 1 d . . .
C07 C 0.3236(3) 0.4128(3) 0.73040(14) 0.0249(6) Uani 1 1 d . . .
C08 C 0.2914(3) 0.2800(3) 0.62626(15) 0.0267(6) Uani 1 1 d . . .
C14 C 0.3977(3) 0.4708(3) 0.57262(14) 0.0245(6) Uani 1 1 d . . .
C17 C 0.7352(3) 0.3911(3) 0.76251(15) 0.0271(6) Uani 1 1 d . . .
C15 C 0.5371(3) 0.4536(2) 0.69049(14) 0.0230(6) Uani 1 1 d . . .
C19 C 0.4652(3) 0.3979(3) 0.73771(14) 0.0245(6) Uani 1 1 d . . .
C01 C 0.2715(3) 0.4920(3) 0.78659(15) 0.0279(6) Uani 1 1 d . . .
C13 C 0.3635(3) 0.3299(3) 0.57426(15) 0.0267(6) Uani 1 1 d . . .
C02 C 0.3478(3) 0.5837(3) 0.82791(15) 0.0292(6) Uani 1 1 d . . .
H02A H 0.4343 0.5957 0.8201 0.035 Uiso 1 1 calc R . .
C12 C 0.3924(3) 0.2512(3) 0.51756(15) 0.0305(7) Uani 1 1 d . . .
H12 H 0.4393 0.2862 0.4816 0.037 Uiso 1 1 calc R . .
C09 C 0.2503(3) 0.1521(3) 0.61949(16) 0.0321(7) Uani 1 1 d . . .
H09 H 0.1992 0.1179 0.6536 0.039 Uiso 1 1 calc R . .
C03 C 0.2978(3) 0.6571(3) 0.88022(17) 0.0339(7) Uani 1 1 d . . .
H03 H 0.3495 0.7205 0.9076 0.041 Uiso 1 1 calc R . .
C16 C 0.7448(3) 0.5227(3) 0.65324(17) 0.0349(7) Uani 1 1 d . . .
H16A H 0.7091 0.5061 0.6022 0.052 Uiso 1 1 calc R . .
H16B H 0.8335 0.4916 0.6620 0.052 Uiso 1 1 calc R . .
H16C H 0.7429 0.6159 0.6630 0.052 Uiso 1 1 calc R . .
C10 C 0.2825(3) 0.0736(3) 0.56409(16) 0.0349(7) Uani 1 1 d . . .
H10 H 0.2556 -0.0143 0.5612 0.042 Uiso 1 1 calc R . .
C11 C 0.3541(3) 0.1232(3) 0.51252(16) 0.0345(7) Uani 1 1 d . . .
H11 H 0.3764 0.0696 0.4743 0.041 Uiso 1 1 calc R . .
C06 C 0.1463(3) 0.4724(4) 0.79966(18) 0.0421(8) Uani 1 1 d . . .
H06 H 0.0939 0.4098 0.7721 0.050 Uiso 1 1 calc R . .
C20 C 0.9216(3) 0.1600(3) 0.91030(19) 0.0412(8) Uani 1 1 d . . .
H20A H 0.9472 0.1980 0.8651 0.049 Uiso 1 1 calc R . .
H20B H 0.9043 0.0667 0.9013 0.049 Uiso 1 1 calc R . .
C04 C 0.1725(3) 0.6379(4) 0.89244(19) 0.0461(9) Uani 1 1 d . . .
H04A H 0.1375 0.6888 0.9278 0.055 Uiso 1 1 calc R . .
C05 C 0.0980(3) 0.5441(4) 0.8529(2) 0.0533(10) Uani 1 1 d . . .
H05 H 0.0129 0.5291 0.8626 0.064 Uiso 1 1 calc R . .
C21 C 1.0291(4) 0.1750(5) 0.9718(2) 0.0644(12) Uani 1 1 d . . .
H21A H 1.0473 0.2673 0.9803 0.097 Uiso 1 1 calc R . .
H21B H 1.1057 0.1316 0.9591 0.097 Uiso 1 1 calc R . .
H21C H 1.0045 0.1361 1.0164 0.097 Uiso 1 1 calc R . .


_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
O01 C18 1.236(3) . ?
O02 C17 1.210(3) . ?
O03 C14 1.226(3) . ?
O04 C20 1.441(4) . ?
O04 H04 0.8400 . ?
N01 C14 1.353(3) . ?
N01 C15 1.405(3) . ?
N01 H01 0.8800 . ?
N02 C18 1.361(3) . ?
N02 C17 1.375(3) . ?
N02 H02 0.8800 . ?
N03 C07 1.281(4) . ?
N03 C08 1.413(3) . ?
N04 C15 1.367(3) . ?
N04 C17 1.396(4) . ?
N04 C16 1.470(3) . ?
C18 C19 1.442(4) . ?
C07 C19 1.487(4) . ?
C07 C01 1.483(4) . ?
C08 C09 1.389(4) . ?
C08 C13 1.400(4) . ?
C14 C13 1.499(4) . ?
C15 C19 1.357(4) . ?
C01 C06 1.387(4) . ?
C01 C02 1.398(4) . ?
C13 C12 1.389(4) . ?
C02 C03 1.385(4) . ?
C02 H02A 0.9500 . ?
C12 C11 1.381(4) . ?
C12 H12 0.9500 . ?
C09 C10 1.381(4) . ?
C09 H09 0.9500 . ?
C03 C04 1.384(4) . ?
C03 H03 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C06 C05 1.381(5) . ?
C06 H06 0.9500 . ?
C20 C21 1.497(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C04 C05 1.388(5) . ?
C04 H04A 0.9500 . ?
C05 H05 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O04 H04 109.5 . . ?
C14 N01 C15 126.0(2) . . ?
C14 N01 H01 117.0 . . ?
C15 N01 H01 117.0 . . ?
C18 N02 C17 126.9(2) . . ?
C18 N02 H02 116.5 . . ?
C17 N02 H02 116.5 . . ?
C07 N03 C08 121.0(2) . . ?
C15 N04 C17 120.9(2) . . ?
C15 N04 C16 122.2(2) . . ?
C17 N04 C16 116.9(2) . . ?
O01 C18 N02 121.3(2) . . ?
O01 C18 C19 123.1(2) . . ?
N02 C18 C19 115.6(2) . . ?
N03 C07 C19 123.7(2) . . ?
N03 C07 C01 119.1(2) . . ?
C19 C07 C01 117.2(2) . . ?
C09 C08 N03 118.6(3) . . ?
C09 C08 C13 118.6(3) . . ?
N03 C08 C13 122.3(2) . . ?
O03 C14 N01 120.2(2) . . ?
O03 C14 C13 120.6(2) . . ?
N01 C14 C13 119.2(2) . . ?
O02 C17 N02 122.4(3) . . ?
O02 C17 N04 122.6(3) . . ?
N02 C17 N04 115.0(2) . . ?
C19 C15 N04 122.8(2) . . ?
C19 C15 N01 121.2(2) . . ?
N04 C15 N01 115.9(2) . . ?
C15 C19 C18 118.6(2) . . ?
C15 C19 C07 122.6(2) . . ?
C18 C19 C07 118.6(2) . . ?
C06 C01 C02 119.6(3) . . ?
C06 C01 C07 119.5(3) . . ?
C02 C01 C07 120.9(2) . . ?
C12 C13 C08 119.7(3) . . ?
C12 C13 C14 118.3(2) . . ?
C08 C13 C14 121.7(2) . . ?
C01 C02 C03 120.3(3) . . ?
C01 C02 H02A 119.9 . . ?
C03 C02 H02A 119.9 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C08 C09 C10 121.3(3) . . ?
C08 C09 H09 119.4 . . ?
C10 C09 H09 119.4 . . ?
C04 C03 C02 119.8(3) . . ?
C04 C03 H03 120.1 . . ?
C02 C03 H03 120.1 . . ?
N04 C16 H16A 109.5 . . ?
N04 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N04 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C09 C10 C11 120.1(3) . . ?
C09 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C01 C06 C05 119.7(3) . . ?
C01 C06 H06 120.1 . . ?
C05 C06 H06 120.1 . . ?
O04 C20 C21 111.5(3) . . ?
O04 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
O04 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C03 C04 C05 119.9(3) . . ?
C03 C04 H04A 120.1 . . ?
C05 C04 H04A 120.1 . . ?
C06 C05 C04 120.7(3) . . ?
C06 C05 H05 119.7 . . ?
C04 C05 H05 119.7 . . ?
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 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.138
