# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_compound-1
_database_code_depnum_ccdc_archive 'CCDC 912003'
_audit_update_record             
;
2012-11-21 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
#TrackingRef 'Deposit Structures Carmen.CIF'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

2-Methyl-5-oxo-3H,5H-pyrrolo
[2,1-a]isoindole-9b-carboxylic acid tert-butylamide

;

_chemical_name_common            ?

_chemical_melting_point          155-158

_chemical_formula_moiety         'C17 H20 N2 O2'

_chemical_formula_sum            'C17 H20 N2 O2'

_chemical_formula_weight         284.35



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 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           Triclinic

_symmetry_space_group_name_H-M   P-1

_symmetry_space_group_name_Hall  '-P 1'





loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   9.074(2)

_cell_length_b                   9.586(2)

_cell_length_c                   10.271(2)

_cell_angle_alpha                105.491(4)

_cell_angle_beta                 97.554(4)

_cell_angle_gamma                108.975(4)

_cell_volume                     790.4(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    1890

_cell_measurement_theta_min      2.38

_cell_measurement_theta_max      23.30



_exptl_crystal_description       Prism

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.18

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      .

_exptl_crystal_density_diffrn    1.195

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             304

_exptl_absorpt_coefficient_mu    0.079

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      298(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 Smart APEX AXS CCD area detector 01-670'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.83

_diffrn_reflns_number            6602

_diffrn_reflns_av_R_equivalents  0.0329

_diffrn_reflns_av_sigmaI/netI    0.0543

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       12

_diffrn_reflns_theta_min         2.12

_diffrn_reflns_theta_max         25.39

_reflns_number_total             2905

_reflns_number_gt                1390

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'

_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'

_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_solved_by                       'Simon Hernandez-Ortega'



_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)+(0.0500P)²] 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         2905

_refine_ls_number_parameters     222

_refine_ls_number_restraints     97

_refine_ls_R_factor_all          0.0941

_refine_ls_R_factor_gt           0.0431

_refine_ls_wR_factor_ref         0.1110

_refine_ls_wR_factor_gt          0.0977

_refine_ls_goodness_of_fit_ref   0.828

_refine_ls_restrained_S_all      0.838

_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





















































O1 O 1.04096(18) 0.39784(17) 0.14419(14) 0.0926(5) Uani 1 1 d . . .
O2 O 0.7590(2) 0.8567(2) 0.29537(15) 0.1111(6) Uani 1 1 d . . .
C1 C 0.9791(3) 0.4856(3) 0.2004(2) 0.0721(6) Uani 1 1 d . . .
N2 N 0.9982(2) 0.6276(2) 0.18527(15) 0.0697(5) Uani 1 1 d . . .
C3 C 1.1544(3) 0.7279(3) 0.1779(2) 0.0867(7) Uani 1 1 d . . .
H3A H 1.1463 0.7575 0.0948 0.104 Uiso 1 1 calc R . .
H3B H 1.2305 0.6765 0.1786 0.104 Uiso 1 1 calc R . .
C4 C 1.2028(3) 0.8671(3) 0.3065(2) 0.0848(7) Uani 1 1 d . . .
C5 C 1.0822(3) 0.8581(3) 0.3718(2) 0.0874(7) Uani 1 1 d . . .
H5 H 1.0896 0.9280 0.4572 0.105 Uiso 1 1 calc R . .
C6 C 0.9320(2) 0.7166(2) 0.28538(19) 0.0685(6) Uani 1 1 d . . .
C7 C 0.7666(3) 0.6153(4) 0.4522(2) 0.0973(8) Uani 1 1 d . . .
H7 H 0.7489 0.7068 0.4878 0.117 Uiso 1 1 calc R . .
C8 C 0.7067(3) 0.4902(5) 0.4988(3) 0.1105(10) Uani 1 1 d . . .
H8 H 0.6485 0.4981 0.5667 0.133 Uiso 1 1 calc R . .
C9 C 0.7316(3) 0.3560(4) 0.4467(3) 0.1052(9) Uani 1 1 d . . .
H9 H 0.6900 0.2734 0.4795 0.126 Uiso 1 1 calc R . .
C10 C 0.8175(3) 0.3398(3) 0.3458(3) 0.0930(7) Uani 1 1 d . . .
H10 H 0.8358 0.2485 0.3111 0.112 Uiso 1 1 calc R . .
C11 C 0.8754(2) 0.4650(3) 0.2985(2) 0.0722(6) Uani 1 1 d . . .
C12 C 0.8520(2) 0.6021(3) 0.3530(2) 0.0720(6) Uani 1 1 d . . .
C13 C 1.3621(3) 0.9898(3) 0.3496(3) 0.1262(10) Uani 1 1 d . . .
H13A H 1.3725 1.0486 0.2867 0.189 Uiso 1 1 calc R . .
H13B H 1.4416 0.9437 0.3487 0.189 Uiso 1 1 calc R . .
H13C H 1.3774 1.0580 0.4420 0.189 Uiso 1 1 calc R . .
C14 C 0.8112(2) 0.7733(2) 0.2186(2) 0.0760(6) Uani 1 1 d . . .
N15 N 0.7710(2) 0.7278(2) 0.08094(17) 0.0710(5) Uani 1 1 d D A .
H15 H 0.822(2) 0.674(2) 0.0370(18) 0.085 Uiso 1 1 d D . .
C16 C 0.6644(3) 0.7763(3) -0.0026(2) 0.0792(6) Uani 1 1 d DU . .
C17 C 0.5024(4) 0.7339(6) 0.0359(6) 0.1082(14) Uani 0.870(12) 1 d PDU A 1
H17A H 0.4557 0.6230 0.0169 0.162 Uiso 0.870(12) 1 calc PR A 1
H17B H 0.4322 0.7650 -0.0181 0.162 Uiso 0.870(12) 1 calc PR A 1
H17C H 0.5174 0.7870 0.1331 0.162 Uiso 0.870(12) 1 calc PR A 1
C18 C 0.7390(7) 0.9488(5) 0.0209(8) 0.1264(16) Uani 0.870(12) 1 d PDU A 1
H18A H 0.7604 1.0060 0.1180 0.190 Uiso 0.870(12) 1 calc PR A 1
H18B H 0.6665 0.9790 -0.0317 0.190 Uiso 0.870(12) 1 calc PR A 1
H18C H 0.8376 0.9714 -0.0088 0.190 Uiso 0.870(12) 1 calc PR A 1
C19 C 0.6358(9) 0.6807(8) -0.1541(3) 0.1080(17) Uani 0.870(12) 1 d PDU A 1
H19A H 0.5809 0.5720 -0.1674 0.162 Uiso 0.870(12) 1 calc PR A 1
H19B H 0.7370 0.6961 -0.1788 0.162 Uiso 0.870(12) 1 calc PR A 1
H19C H 0.5716 0.7137 -0.2120 0.162 Uiso 0.870(12) 1 calc PR A 1
C17A C 0.4841(18) 0.706(4) -0.027(4) 0.128(8) Uani 0.130(12) 1 d PDU A 2
H17D H 0.4497 0.5956 -0.0446 0.193 Uiso 0.130(12) 1 calc PR A 2
H17E H 0.4353 0.7253 -0.1057 0.193 Uiso 0.130(12) 1 calc PR A 2
H17F H 0.4526 0.7531 0.0540 0.193 Uiso 0.130(12) 1 calc PR A 2
C18A C 0.720(4) 0.9531(19) 0.083(3) 0.098(6) Uani 0.130(12) 1 d PDU A 2
H18D H 0.8264 1.0079 0.0767 0.147 Uiso 0.130(12) 1 calc PR A 2
H18E H 0.7184 0.9649 0.1784 0.147 Uiso 0.130(12) 1 calc PR A 2
H18F H 0.6479 0.9955 0.0457 0.147 Uiso 0.130(12) 1 calc PR A 2
C19A C 0.728(4) 0.767(5) -0.136(2) 0.092(4) Uani 0.130(12) 1 d PDU A 2
H19D H 0.8401 0.8312 -0.1110 0.137 Uiso 0.130(12) 1 calc PR A 2
H19E H 0.6705 0.8046 -0.1951 0.137 Uiso 0.130(12) 1 calc PR A 2
H19F H 0.7120 0.6611 -0.1838 0.137 Uiso 0.130(12) 1 calc PR A 2






_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag























































O1 C1 1.220(2) . ?
O2 C14 1.221(2) . ?
C1 N2 1.369(2) . ?
C1 C11 1.474(3) . ?
N2 C3 1.456(2) . ?
N2 C6 1.474(2) . ?
C3 C4 1.498(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.348(3) . ?
C4 C13 1.455(3) . ?
C5 C6 1.524(3) . ?
C5 H5 0.9300 . ?
C6 C12 1.495(3) . ?
C6 C14 1.535(3) . ?
C7 C12 1.362(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N15 1.324(2) . ?
N15 C16 1.475(2) . ?
N15 H15 0.876(9) . ?
C16 C18 1.506(4) . ?
C16 C17A 1.510(14) . ?
C16 C19 1.519(3) . ?
C16 C17 1.527(3) . ?
C16 C19A 1.544(12) . ?
C16 C18A 1.559(13) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 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















































































































O1 C1 N2 125.1(2) . . ?
O1 C1 C11 128.3(2) . . ?
N2 C1 C11 106.64(19) . . ?
C1 N2 C3 119.55(17) . . ?
C1 N2 C6 111.52(17) . . ?
C3 N2 C6 110.73(17) . . ?
N2 C3 C4 103.23(17) . . ?
N2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
N2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C13 127.4(2) . . ?
C5 C4 C3 110.9(2) . . ?
C13 C4 C3 121.7(2) . . ?
C4 C5 C6 110.2(2) . . ?
C4 C5 H5 124.9 . . ?
C6 C5 H5 124.9 . . ?
N2 C6 C12 103.03(17) . . ?
N2 C6 C5 101.50(16) . . ?
C12 C6 C5 118.47(17) . . ?
N2 C6 C14 114.23(16) . . ?
C12 C6 C14 110.64(17) . . ?
C5 C6 C14 108.75(17) . . ?
C12 C7 C8 118.8(3) . . ?
C12 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 117.4(2) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 C1 109.1(2) . . ?
C10 C11 C1 129.4(2) . . ?
C7 C12 C11 120.4(2) . . ?
C7 C12 C6 130.6(2) . . ?
C11 C12 C6 109.01(19) . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N15 124.69(19) . . ?
O2 C14 C6 118.12(19) . . ?
N15 C14 C6 117.19(17) . . ?
C14 N15 C16 125.50(16) . . ?
C14 N15 H15 116.4(13) . . ?
C16 N15 H15 117.7(13) . . ?
N15 C16 C18 110.6(3) . . ?
N15 C16 C17A 122.1(17) . . ?
C18 C16 C17A 116.8(17) . . ?
N15 C16 C19 107.33(19) . . ?
C18 C16 C19 111.3(3) . . ?
C17A C16 C19 85.0(12) . . ?
N15 C16 C17 109.0(3) . . ?
C18 C16 C17 111.1(3) . . ?
C17A C16 C17 23.0(13) . . ?
C19 C16 C17 107.4(3) . . ?
N15 C16 C19A 102.8(8) . . ?
C18 C16 C19A 81.5(13) . . ?
C17A C16 C19A 115.1(12) . . ?
C19 C16 C19A 34.9(13) . . ?
C17 C16 C19A 137.9(12) . . ?
N15 C16 C18A 101.5(13) . . ?
C18 C16 C18A 25.4(12) . . ?
C17A C16 C18A 107.1(15) . . ?
C19 C16 C18A 136.0(12) . . ?
C17 C16 C18A 93.4(13) . . ?
C19A C16 C18A 106.7(12) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17A H17D 109.5 . . ?
C16 C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C16 C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C16 C18A H18D 109.5 . . ?
C16 C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C16 C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C16 C19A H19D 109.5 . . ?
C16 C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C16 C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?



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






















































O1 C1 N2 C3 -38.5(3) . . . . ?
C11 C1 N2 C3 140.05(17) . . . . ?
O1 C1 N2 C6 -169.87(18) . . . . ?
C11 C1 N2 C6 8.7(2) . . . . ?
C1 N2 C3 C4 -115.25(19) . . . . ?
C6 N2 C3 C4 16.5(2) . . . . ?
N2 C3 C4 C5 -6.6(2) . . . . ?
N2 C3 C4 C13 172.4(2) . . . . ?
C13 C4 C5 C6 175.8(2) . . . . ?
C3 C4 C5 C6 -5.2(3) . . . . ?
C1 N2 C6 C12 -6.4(2) . . . . ?
C3 N2 C6 C12 -142.17(16) . . . . ?
C1 N2 C6 C5 116.68(18) . . . . ?
C3 N2 C6 C5 -19.0(2) . . . . ?
C1 N2 C6 C14 -126.50(19) . . . . ?
C3 N2 C6 C14 97.8(2) . . . . ?
C4 C5 C6 N2 14.6(2) . . . . ?
C4 C5 C6 C12 126.5(2) . . . . ?
C4 C5 C6 C14 -106.1(2) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 1.9(3) . . . . ?
C9 C10 C11 C1 175.2(2) . . . . ?
O1 C1 C11 C12 170.9(2) . . . . ?
N2 C1 C11 C12 -7.6(2) . . . . ?
O1 C1 C11 C10 -3.1(3) . . . . ?
N2 C1 C11 C10 178.4(2) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C8 C7 C12 C6 -179.0(2) . . . . ?
C10 C11 C12 C7 -2.1(3) . . . . ?
C1 C11 C12 C7 -176.63(17) . . . . ?
C10 C11 C12 C6 178.14(18) . . . . ?
C1 C11 C12 C6 3.6(2) . . . . ?
N2 C6 C12 C7 -178.30(19) . . . . ?
C5 C6 C12 C7 70.7(3) . . . . ?
C14 C6 C12 C7 -55.8(3) . . . . ?
N2 C6 C12 C11 1.4(2) . . . . ?
C5 C6 C12 C11 -109.6(2) . . . . ?
C14 C6 C12 C11 123.93(18) . . . . ?
N2 C6 C14 O2 -175.2(2) . . . . ?
C12 C6 C14 O2 69.1(3) . . . . ?
C5 C6 C14 O2 -62.7(3) . . . . ?
N2 C6 C14 N15 4.8(3) . . . . ?
C12 C6 C14 N15 -110.9(2) . . . . ?
C5 C6 C14 N15 117.4(2) . . . . ?
O2 C14 N15 C16 3.5(4) . . . . ?
C6 C14 N15 C16 -176.5(2) . . . . ?
C14 N15 C16 C18 65.3(4) . . . . ?
C14 N15 C16 C17A -78.1(17) . . . . ?
C14 N15 C16 C19 -173.1(4) . . . . ?
C14 N15 C16 C17 -57.1(3) . . . . ?
C14 N15 C16 C19A 151.0(16) . . . . ?
C14 N15 C16 C18A 40.6(14) . . . . ?



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


N15 H15 N2 0.876(9) 2.293(18) 2.752(2) 112.7(15) .
N15 H15 O1 0.876(9) 2.444(12) 3.255(2) 154.0(17) 2_765



_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.39

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.123

_refine_diff_density_min         -0.118

_refine_diff_density_rms         0.024
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 912004'
_audit_update_record             
;
2012-11-21 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
#TrackingRef 'Deposit Structures Carmen.CIF'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;2-Methylene-6-oxo-1,2,3,4-tetrahydro-6H-pyrido
[2,1-a]isoindole-10b-carboxylic acid tert-butylamide

;

_chemical_name_common            ?

_chemical_melting_point          208-210

_chemical_formula_moiety         'C18 H22 N2 O2'

_chemical_formula_sum            'C18 H22 N2 O2'

_chemical_formula_weight         298.38



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'

_symmetry_space_group_name_Hall  '-P 2ybc'





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                   9.1496(13)

_cell_length_b                   9.3085(13)

_cell_length_c                   19.945(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 95.325(2)

_cell_angle_gamma                90.00

_cell_volume                     1691.3(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    3292

_cell_measurement_theta_min      2.42

_cell_measurement_theta_max      24.70



_exptl_crystal_description       Prism

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.36

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      .

_exptl_crystal_density_diffrn    1.172

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.077

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      298(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 Smart APEX AXS CCD area detector'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.83

_diffrn_reflns_number            13090

_diffrn_reflns_av_R_equivalents  0.0645

_diffrn_reflns_av_sigmaI/netI    0.0588

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -23

_diffrn_reflns_limit_l_max       24

_diffrn_reflns_theta_min         2.05

_diffrn_reflns_theta_max         25.35

_reflns_number_total             3088

_reflns_number_gt                1577

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'

_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'

_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_solved_by                       'Simon Hernandez-Ortega'



_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)+(0.0710P)²] 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         3088

_refine_ls_number_parameters     222

_refine_ls_number_restraints     70

_refine_ls_R_factor_all          0.1136

_refine_ls_R_factor_gt           0.0540

_refine_ls_wR_factor_ref         0.1462

_refine_ls_wR_factor_gt          0.1274

_refine_ls_goodness_of_fit_ref   0.943

_refine_ls_restrained_S_all      0.972

_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



















































O1 O 0.38637(19) -0.1024(2) 0.52499(10) 0.0758(6) Uani 1 1 d . . .
O2 O 0.1758(2) 0.3824(2) 0.36630(10) 0.0865(7) Uani 1 1 d . B .
C1 C 0.3177(3) 0.0051(3) 0.50378(14) 0.0574(7) Uani 1 1 d . . .
N2 N 0.2891(2) 0.0402(2) 0.43864(10) 0.0553(6) Uani 1 1 d . B .
C3 C 0.1909(2) 0.1631(3) 0.42725(12) 0.0516(6) Uani 1 1 d . B .
C4 C 0.0851(3) 0.3140(3) 0.52221(16) 0.0800(9) Uani 1 1 d . . .
H4 H 0.0297 0.3738 0.4924 0.096 Uiso 1 1 calc R . .
C5 C 0.0840(4) 0.3317(4) 0.59048(19) 0.0909(10) Uani 1 1 d . . .
H5 H 0.0285 0.4050 0.6071 0.109 Uiso 1 1 calc R . .
C6 C 0.1645(4) 0.2419(4) 0.63445(16) 0.0848(10) Uani 1 1 d . . .
H6 H 0.1632 0.2557 0.6806 0.102 Uiso 1 1 calc R . .
C7 C 0.2465(3) 0.1326(3) 0.61151(14) 0.0712(8) Uani 1 1 d . . .
H7 H 0.2994 0.0711 0.6414 0.085 Uiso 1 1 calc R . .
C8 C 0.2486(3) 0.1158(3) 0.54300(12) 0.0548(7) Uani 1 1 d . . .
C9 C 0.1697(3) 0.2061(3) 0.49875(13) 0.0589(7) Uani 1 1 d . . .
C10 C 0.3215(3) -0.0493(3) 0.38312(14) 0.0753(8) Uani 1 1 d D . .
H10A H 0.3819 -0.1293 0.4003 0.090 Uiso 1 1 calc R A 1
H10B H 0.3780 0.0059 0.3533 0.090 Uiso 1 1 calc R A 1
C12 C 0.0876(9) 0.0176(11) 0.3287(3) 0.0780(19) Uani 0.677(9) 1 d PDU B 1
C11 C 0.1901(5) -0.1057(8) 0.3443(3) 0.0893(16) Uani 0.677(9) 1 d PDU B 1
H11A H 0.1436 -0.1779 0.3703 0.107 Uiso 0.677(9) 1 calc PR B 1
H11B H 0.2162 -0.1496 0.3030 0.107 Uiso 0.677(9) 1 calc PR B 1
C14 C 0.0201(9) 0.0407(10) 0.2648(3) 0.113(2) Uani 0.677(9) 1 d PDU B 1
H14A H 0.0379 -0.0214 0.2300 0.136 Uiso 0.677(9) 1 calc PR B 1
H14B H -0.0430 0.1183 0.2567 0.136 Uiso 0.677(9) 1 calc PR B 1
C12A C 0.071(2) 0.052(3) 0.3194(6) 0.086(3) Uani 0.323(9) 1 d PDU B 2
C11A C 0.2040(11) -0.0328(17) 0.3246(5) 0.0893(16) Uani 0.323(9) 1 d PDU B 2
H11C H 0.2566 -0.0015 0.2872 0.107 Uiso 0.323(9) 1 calc PR B 2
H11D H 0.1717 -0.1300 0.3138 0.107 Uiso 0.323(9) 1 calc PR B 2
C14A C -0.0412(16) 0.062(2) 0.2702(9) 0.115(5) Uiso 0.323(9) 1 d PDU B 2
H14C H -0.0401 0.0082 0.2311 0.138 Uiso 0.323(9) 1 calc PR B 2
H14D H -0.1194 0.1238 0.2757 0.138 Uiso 0.323(9) 1 calc PR B 2
C13 C 0.0491(3) 0.1127(3) 0.38719(14) 0.0781(9) Uani 1 1 d D . .
H13A H -0.0101 0.0589 0.4163 0.094 Uiso 1 1 calc R B 1
H13B H -0.0072 0.1952 0.3699 0.094 Uiso 1 1 calc R B 1
C15 C 0.2577(3) 0.2900(3) 0.39171(12) 0.0575(7) Uani 1 1 d . . .
N16 N 0.4033(2) 0.2937(2) 0.39269(10) 0.0589(6) Uani 1 1 d D B .
H16 H 0.455(2) 0.225(2) 0.4145(11) 0.071 Uiso 1 1 d D . .
C17 C 0.4889(3) 0.4051(3) 0.36210(14) 0.0676(8) Uani 1 1 d . . .
C18 C 0.6490(3) 0.3618(4) 0.3730(2) 0.1189(14) Uani 1 1 d . B .
H18A H 0.6792 0.3591 0.4204 0.178 Uiso 1 1 calc R . .
H18B H 0.7078 0.4304 0.3516 0.178 Uiso 1 1 calc R . .
H18C H 0.6615 0.2684 0.3538 0.178 Uiso 1 1 calc R . .
C19 C 0.4431(4) 0.4132(5) 0.28717(16) 0.1227(14) Uani 1 1 d . B .
H19A H 0.4576 0.3214 0.2669 0.184 Uiso 1 1 calc R . .
H19B H 0.5014 0.4842 0.2670 0.184 Uiso 1 1 calc R . .
H19C H 0.3414 0.4394 0.2801 0.184 Uiso 1 1 calc R . .
C20 C 0.4656(5) 0.5496(4) 0.3942(2) 0.1278(14) Uani 1 1 d . B .
H20A H 0.3630 0.5732 0.3890 0.192 Uiso 1 1 calc R . .
H20B H 0.5199 0.6218 0.3726 0.192 Uiso 1 1 calc R . .
H20C H 0.4990 0.5456 0.4412 0.192 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






















































O1 C1 1.235(3) . ?
O2 C15 1.221(3) . ?
C1 N2 1.342(3) . ?
C1 C8 1.472(4) . ?
N2 C10 1.439(3) . ?
N2 C3 1.459(3) . ?
C3 C9 1.511(3) . ?
C3 C13 1.532(3) . ?
C3 C15 1.533(3) . ?
C4 C5 1.372(4) . ?
C4 C9 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(3) . ?
C10 C11 1.466(5) . ?
C10 C11A 1.519(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C14 1.379(6) . ?
C12 C11 1.497(6) . ?
C12 C13 1.531(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C12A C14A 1.359(9) . ?
C12A C11A 1.442(9) . ?
C12A C13 1.498(8) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C14A H14C 0.9300 . ?
C14A H14D 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 N16 1.331(3) . ?
N16 C17 1.467(3) . ?
N16 H16 0.887(10) . ?
C17 C20 1.513(4) . ?
C17 C18 1.515(4) . ?
C17 C19 1.516(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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






































































































O1 C1 N2 125.2(3) . . ?
O1 C1 C8 128.0(2) . . ?
N2 C1 C8 106.8(2) . . ?
C1 N2 C10 124.6(2) . . ?
C1 N2 C3 113.8(2) . . ?
C10 N2 C3 120.2(2) . . ?
N2 C3 C9 101.06(19) . . ?
N2 C3 C13 108.7(2) . . ?
C9 C3 C13 113.4(2) . . ?
N2 C3 C15 114.17(19) . . ?
C9 C3 C15 108.9(2) . . ?
C13 C3 C15 110.4(2) . . ?
C5 C4 C9 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C9 C4 H4 120.6 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 118.3(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 C1 108.2(2) . . ?
C7 C8 C1 130.8(3) . . ?
C8 C9 C4 120.4(3) . . ?
C8 C9 C3 109.8(2) . . ?
C4 C9 C3 129.8(2) . . ?
N2 C10 C11 113.3(3) . . ?
N2 C10 C11A 110.5(5) . . ?
N2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C11A C10 H10A 133.5 . . ?
N2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C11A C10 H10B 81.7 . . ?
H10A C10 H10B 107.7 . . ?
C14 C12 C11 122.0(5) . . ?
C14 C12 C13 119.9(6) . . ?
C11 C12 C13 117.9(4) . . ?
C10 C11 C12 107.6(5) . . ?
C10 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C12 C14 H14A 120.0 . . ?
C12 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C14A C12A C11A 132.0(9) . . ?
C14A C12A C13 117.8(12) . . ?
C11A C12A C13 109.0(9) . . ?
C12A C11A C10 129.9(10) . . ?
C12A C11A H11C 104.8 . . ?
C10 C11A H11C 104.8 . . ?
C12A C11A H11D 104.8 . . ?
C10 C11A H11D 104.8 . . ?
H11C C11A H11D 105.8 . . ?
C12A C14A H14C 120.0 . . ?
C12A C14A H14D 120.0 . . ?
H14C C14A H14D 120.0 . . ?
C12A C13 C3 114.0(8) . . ?
C12 C13 C3 109.3(4) . . ?
C12A C13 H13A 118.4 . . ?
C12 C13 H13A 109.8 . . ?
C3 C13 H13A 109.8 . . ?
C12A C13 H13B 95.3 . . ?
C12 C13 H13B 109.8 . . ?
C3 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
O2 C15 N16 124.3(2) . . ?
O2 C15 C3 118.6(2) . . ?
N16 C15 C3 117.1(2) . . ?
C15 N16 C17 125.8(2) . . ?
C15 N16 H16 118.5(16) . . ?
C17 N16 H16 115.7(16) . . ?
N16 C17 C20 110.5(2) . . ?
N16 C17 C18 107.4(2) . . ?
C20 C17 C18 110.4(3) . . ?
N16 C17 C19 109.6(2) . . ?
C20 C17 C19 109.6(3) . . ?
C18 C17 C19 109.2(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?



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

N16 H16 O1 0.887(10) 2.129(12) 2.997(3) 166(2) 3_656



_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.35

_diffrn_measured_fraction_theta_full 0.999

_refine_diff_density_max         0.179

_refine_diff_density_min         -0.138

_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 912005'
_audit_update_record             
;
2012-11-21 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
#TrackingRef 'Deposit Structures Carmen.CIF'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;7-Oxo-5,12-dihydro-7H-isoindolo
[2,1-b]isoquinoline-11b-carboxylic acid tert-butylamide

;

_chemical_name_common            ?

_chemical_melting_point          208-210

_chemical_formula_moiety         'C21 H22 N2 O2'

_chemical_formula_sum            'C21 H22 N2 O2'

_chemical_formula_weight         334.41



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source








C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Triclinic

_symmetry_space_group_name_H-M   'P -1'

_symmetry_space_group_name_Hall  '-P 1'





loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   9.2332(15)

_cell_length_b                   10.3088(17)

_cell_length_c                   10.7141(18)

_cell_angle_alpha                105.017(3)

_cell_angle_beta                 100.269(3)

_cell_angle_gamma                102.043(3)

_cell_volume                     933.7(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    3230

_cell_measurement_theta_min      0.00

_cell_measurement_theta_max      0.00



_exptl_crystal_description       Prism

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.34

_exptl_crystal_size_mid          0.18

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      .

_exptl_crystal_density_diffrn    1.189

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             356

_exptl_absorpt_coefficient_mu    0.077

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      298(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 Smart APEX AXS CCD area detector 01-670'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.83

_diffrn_reflns_number            7775

_diffrn_reflns_av_R_equivalents  0.0371

_diffrn_reflns_av_sigmaI/netI    0.0466

_diffrn_reflns_limit_h_min       -11

_diffrn_reflns_limit_h_max       11

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       12

_diffrn_reflns_theta_min         2.03

_diffrn_reflns_theta_max         25.38

_reflns_number_total             3415

_reflns_number_gt                2274

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'

_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'

_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_solved_by                       'Simon Hernandez-Ortega'



_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)+(0.0639P)²] 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         3415

_refine_ls_number_parameters     232

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0707

_refine_ls_R_factor_gt           0.0462

_refine_ls_wR_factor_ref         0.1180

_refine_ls_wR_factor_gt          0.1081

_refine_ls_goodness_of_fit_ref   0.922

_refine_ls_restrained_S_all      0.922

_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















































O1 O 0.07545(14) 0.66786(12) 0.61825(13) 0.0675(4) Uani 1 1 d . . .
O2 O 0.55274(15) 0.89596(12) 0.39529(14) 0.0718(4) Uani 1 1 d . . .
N1 N 0.21543(15) 0.88656(13) 0.65348(14) 0.0483(4) Uani 1 1 d D . .
H1 H 0.2872(15) 0.9405(15) 0.6307(16) 0.058 Uiso 1 1 d D . .
N2 N 0.41524(14) 0.78443(13) 0.51320(14) 0.0457(4) Uani 1 1 d . . .
C1 C 0.4325(2) 0.82567(16) 0.40504(19) 0.0532(5) Uani 1 1 d . . .
C3 C 0.26506(17) 0.69139(15) 0.49526(16) 0.0419(4) Uani 1 1 d . . .
C4 C 0.0401(2) 0.61124(18) 0.28327(18) 0.0566(5) Uani 1 1 d . . .
H4 H -0.0263 0.5576 0.3179 0.068 Uiso 1 1 calc R . .
C5 C -0.0038(3) 0.6189(2) 0.1567(2) 0.0733(6) Uani 1 1 d . . .
H5 H -0.1013 0.5692 0.1045 0.088 Uiso 1 1 calc R . .
C6 C 0.0941(3) 0.6989(2) 0.1054(2) 0.0820(7) Uani 1 1 d . . .
H6 H 0.0611 0.7027 0.0195 0.098 Uiso 1 1 calc R . .
C7 C 0.2395(3) 0.7733(2) 0.1788(2) 0.0734(6) Uani 1 1 d . . .
H7 H 0.3055 0.8270 0.1439 0.088 Uiso 1 1 calc R . .
C8 C 0.2843(2) 0.76532(16) 0.30662(18) 0.0526(5) Uani 1 1 d . . .
C9 C 0.18561(19) 0.68547(16) 0.35739(17) 0.0456(4) Uani 1 1 d . . .
C10 C 0.5392(2) 0.80567(17) 0.62661(19) 0.0603(5) Uani 1 1 d . . .
H10A H 0.5470 0.8919 0.6942 0.072 Uiso 1 1 calc R . .
H10B H 0.6343 0.8154 0.5988 0.072 Uiso 1 1 calc R . .
C11 C 0.51879(19) 0.68843(17) 0.68670(18) 0.0514(4) Uani 1 1 d . . .
C12 C 0.6232(2) 0.7012(2) 0.8026(2) 0.0729(6) Uani 1 1 d . . .
H12 H 0.7021 0.7826 0.8427 0.087 Uiso 1 1 calc R . .
C13 C 0.6113(3) 0.5950(3) 0.8586(2) 0.0865(7) Uani 1 1 d . . .
H13 H 0.6827 0.6046 0.9359 0.104 Uiso 1 1 calc R . .
C14 C 0.4949(3) 0.4746(2) 0.8013(2) 0.0770(6) Uani 1 1 d . . .
H14 H 0.4874 0.4025 0.8390 0.092 Uiso 1 1 calc R . .
C15 C 0.3898(2) 0.46183(19) 0.68801(19) 0.0589(5) Uani 1 1 d . . .
H15 H 0.3100 0.3809 0.6501 0.071 Uiso 1 1 calc R . .
C16 C 0.39996(18) 0.56703(16) 0.62870(17) 0.0468(4) Uani 1 1 d . . .
C17 C 0.28541(18) 0.55017(15) 0.50301(16) 0.0456(4) Uani 1 1 d . . .
H17A H 0.1881 0.4905 0.5007 0.055 Uiso 1 1 calc R . .
H17B H 0.3196 0.5058 0.4264 0.055 Uiso 1 1 calc R . .
C18 C 0.17722(17) 0.74900(16) 0.59701(16) 0.0433(4) Uani 1 1 d . . .
C19 C 0.1400(2) 0.95996(18) 0.74865(19) 0.0610(5) Uani 1 1 d . . .
C20 C 0.2194(3) 1.1137(2) 0.7902(3) 0.1107(10) Uani 1 1 d . . .
H20A H 0.3264 1.1286 0.8272 0.166 Uiso 1 1 calc R . .
H20B H 0.1760 1.1639 0.8559 0.166 Uiso 1 1 calc R . .
H20C H 0.2063 1.1464 0.7138 0.166 Uiso 1 1 calc R . .
C21 C -0.0271(3) 0.9341(3) 0.6834(3) 0.1255(11) Uani 1 1 d . . .
H21A H -0.0361 0.9686 0.6080 0.188 Uiso 1 1 calc R . .
H21B H -0.0755 0.9815 0.7464 0.188 Uiso 1 1 calc R . .
H21C H -0.0758 0.8359 0.6542 0.188 Uiso 1 1 calc R . .
C22 C 0.1560(4) 0.9100(3) 0.8696(3) 0.1348(12) Uani 1 1 d . . .
H22A H 0.1047 0.8125 0.8435 0.202 Uiso 1 1 calc R . .
H22B H 0.1113 0.9612 0.9334 0.202 Uiso 1 1 calc R . .
H22C H 0.2623 0.9245 0.9088 0.202 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


















































O1 C18 1.2171(17) . ?
O2 C1 1.2299(19) . ?
N1 C18 1.3311(19) . ?
N1 C19 1.474(2) . ?
N1 H1 0.884(9) . ?
N2 C1 1.357(2) . ?
N2 C10 1.448(2) . ?
N2 C3 1.4608(18) . ?
C1 C8 1.470(3) . ?
C3 C9 1.507(2) . ?
C3 C17 1.527(2) . ?
C3 C18 1.543(2) . ?
C4 C5 1.372(3) . ?
C4 C9 1.377(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(2) . ?
C10 C11 1.504(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.387(3) . ?
C11 C16 1.392(2) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.502(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C22 1.508(3) . ?
C19 C20 1.510(3) . ?
C19 C21 1.512(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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


























































































C18 N1 C19 124.55(13) . . ?
C18 N1 H1 119.7(11) . . ?
C19 N1 H1 115.6(11) . . ?
C1 N2 C10 124.28(14) . . ?
C1 N2 C3 113.78(14) . . ?
C10 N2 C3 120.90(13) . . ?
O2 C1 N2 124.48(18) . . ?
O2 C1 C8 129.25(17) . . ?
N2 C1 C8 106.23(14) . . ?
N2 C3 C9 101.39(12) . . ?
N2 C3 C17 108.59(13) . . ?
C9 C3 C17 112.68(13) . . ?
N2 C3 C18 113.46(12) . . ?
C9 C3 C18 110.06(13) . . ?
C17 C3 C18 110.43(12) . . ?
C5 C4 C9 117.89(18) . . ?
C5 C4 H4 121.1 . . ?
C9 C4 H4 121.1 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 117.65(19) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C9 C8 C7 120.72(19) . . ?
C9 C8 C1 108.91(15) . . ?
C7 C8 C1 130.30(18) . . ?
C4 C9 C8 121.29(17) . . ?
C4 C9 C3 129.06(15) . . ?
C8 C9 C3 109.62(15) . . ?
N2 C10 C11 113.03(14) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C16 119.12(17) . . ?
C12 C11 C10 118.76(16) . . ?
C16 C11 C10 122.11(16) . . ?
C13 C12 C11 120.65(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.31(19) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.38(18) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 119.06(17) . . ?
C15 C16 C17 120.68(15) . . ?
C11 C16 C17 120.27(15) . . ?
C16 C17 C3 110.82(13) . . ?
C16 C17 H17A 109.5 . . ?
C3 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
O1 C18 N1 123.99(15) . . ?
O1 C18 C3 118.82(14) . . ?
N1 C18 C3 117.16(13) . . ?
N1 C19 C22 109.60(17) . . ?
N1 C19 C20 107.58(14) . . ?
C22 C19 C20 109.4(2) . . ?
N1 C19 C21 110.11(17) . . ?
C22 C19 C21 110.1(2) . . ?
C20 C19 C21 110.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?



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 N2 C1 O2 -6.4(2) . . . . ?
C3 N2 C1 O2 -174.77(14) . . . . ?
C10 N2 C1 C8 171.54(14) . . . . ?
C3 N2 C1 C8 3.15(17) . . . . ?
C1 N2 C3 C9 -2.56(16) . . . . ?
C10 N2 C3 C9 -171.38(13) . . . . ?
C1 N2 C3 C17 116.30(15) . . . . ?
C10 N2 C3 C17 -52.52(18) . . . . ?
C1 N2 C3 C18 -120.52(14) . . . . ?
C10 N2 C3 C18 70.67(18) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C1 176.33(17) . . . . ?
O2 C1 C8 C9 175.36(16) . . . . ?
N2 C1 C8 C9 -2.43(17) . . . . ?
O2 C1 C8 C7 -1.4(3) . . . . ?
N2 C1 C8 C7 -179.15(17) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
C5 C4 C9 C3 -177.28(16) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C1 C8 C9 C4 -177.01(14) . . . . ?
C7 C8 C9 C3 177.96(15) . . . . ?
C1 C8 C9 C3 0.87(17) . . . . ?
N2 C3 C9 C4 178.55(15) . . . . ?
C17 C3 C9 C4 62.7(2) . . . . ?
C18 C3 C9 C4 -61.1(2) . . . . ?
N2 C3 C9 C8 0.89(16) . . . . ?
C17 C3 C9 C8 -115.00(15) . . . . ?
C18 C3 C9 C8 121.28(14) . . . . ?
C1 N2 C10 C11 -145.17(16) . . . . ?
C3 N2 C10 C11 22.4(2) . . . . ?
N2 C10 C11 C12 -174.78(16) . . . . ?
N2 C10 C11 C16 6.2(2) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
C10 C11 C12 C13 -178.11(19) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C14 C15 C16 C17 178.83(17) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C10 C11 C16 C15 178.67(16) . . . . ?
C12 C11 C16 C17 -179.85(15) . . . . ?
C10 C11 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C3 150.79(15) . . . . ?
C11 C16 C17 C3 -29.7(2) . . . . ?
N2 C3 C17 C16 53.14(17) . . . . ?
C9 C3 C17 C16 164.62(13) . . . . ?
C18 C3 C17 C16 -71.86(16) . . . . ?
C19 N1 C18 O1 -0.3(3) . . . . ?
C19 N1 C18 C3 177.57(15) . . . . ?
N2 C3 C18 O1 -158.46(15) . . . . ?
C9 C3 C18 O1 88.74(18) . . . . ?
C17 C3 C18 O1 -36.3(2) . . . . ?
N2 C3 C18 N1 23.5(2) . . . . ?
C9 C3 C18 N1 -89.28(16) . . . . ?
C17 C3 C18 N1 145.69(14) . . . . ?
C18 N1 C19 C22 60.2(2) . . . . ?
C18 N1 C19 C20 178.99(19) . . . . ?
C18 N1 C19 C21 -61.1(2) . . . . ?



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

N1 H1 O2 0.884(9) 2.111(10) 2.9807(17) 167.8(15) 2_676



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        25.38

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         0.144

_refine_diff_density_min         -0.199

_refine_diff_density_rms         0.043


#==============================================================================



