# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_AZ63M
_database_code_depnum_ccdc_archive 'CCDC 1479998'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-(8-methoxy-4H-benzo[g][1,2,3]triazolo[5,1-c][1,4]oxazocin-11-yl)(phenyl)methanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N3 O3'
_chemical_formula_sum            'C19 H15 N3 O3'
_chemical_formula_weight         333.34

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

_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                   6.5491(5)
_cell_length_b                   18.5820(13)
_cell_length_c                   12.9625(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.3610(10)
_cell_angle_gamma                90
_cell_volume                     1574.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3921
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      23.67

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15034
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.918
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2774
_reflns_number_gt                2539
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.9417P] 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         2774
_refine_ls_number_parameters     237
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.243
_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 0.9026(5) 0.0887(2) 1.1294(2) 0.0700(9) Uani 1 1 d . . . . .
H1A H 0.8891 0.0374 1.1255 0.105 Uiso 1 1 calc R U . . .
H1B H 0.9681 0.1018 1.1949 0.105 Uiso 1 1 calc R U . . .
H1C H 0.9836 0.1053 1.0748 0.105 Uiso 1 1 calc R U . . .
C2 C 0.5923(4) 0.11071(12) 1.02888(18) 0.0398(6) Uani 1 1 d . . . . .
C3 C 0.6478(4) 0.06958(12) 0.94706(17) 0.0372(5) Uani 1 1 d . . . . .
H3 H 0.7734 0.0461 0.9511 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5185(4) 0.06249(12) 0.85765(17) 0.0378(5) Uani 1 1 d . . . . .
C5 C 0.3292(4) 0.09604(15) 0.85460(19) 0.0500(7) Uani 1 1 d D . . . .
C6 C 0.2765(4) 0.13812(16) 0.9375(2) 0.0574(8) Uani 1 1 d . . . . .
H6 H 0.1506 0.1614 0.9346 0.069 Uiso 1 1 calc R U . . .
C7 C 0.4061(4) 0.14585(14) 1.0228(2) 0.0524(7) Uani 1 1 d . . . . .
H7 H 0.3691 0.1748 1.0772 0.063 Uiso 1 1 calc R U . . .
C8 C 0.1832(4) 0.10152(15) 0.67875(19) 0.0471(6) Uani 1 1 d . . . . .
H8A H 0.0745 0.1368 0.6809 0.056 Uiso 1 1 calc R U . A 1
H8B H 0.1414 0.0666 0.6261 0.056 Uiso 1 1 calc R U . A 1
C9 C 0.3677(3) 0.13858(12) 0.64530(17) 0.0363(5) Uani 1 1 d . . . . .
C10 C 0.4011(4) 0.20592(14) 0.6101(2) 0.0493(7) Uani 1 1 d . . . . .
H10 H 0.3026 0.2419 0.6025 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6088(3) 0.03538(12) 0.67604(17) 0.0334(5) Uani 1 1 d . . . . .
C12 C 0.5918(4) 0.01700(13) 0.77412(18) 0.0405(6) Uani 1 1 d . . . . .
H12 H 0.6303 -0.0297 0.7922 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6939(3) -0.01205(13) 0.59604(17) 0.0357(5) Uani 1 1 d . . . . .
C14 C 0.7298(4) -0.08979(13) 0.62000(17) 0.0377(5) Uani 1 1 d . . . . .
C15 C 0.5849(4) -0.13298(14) 0.66202(19) 0.0490(6) Uani 1 1 d . . . . .
H15 H 0.4600 -0.1138 0.6789 0.059 Uiso 1 1 calc R U . . .
C16 C 0.6271(6) -0.20540(15) 0.6789(2) 0.0649(8) Uani 1 1 d . . . . .
H16 H 0.5301 -0.2350 0.7069 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8131(6) -0.23346(16) 0.6542(2) 0.0680(9) Uani 1 1 d . . . . .
H17 H 0.8415 -0.2819 0.6664 0.082 Uiso 1 1 calc R U . . .
C18 C 0.9557(5) -0.19071(16) 0.6120(2) 0.0615(8) Uani 1 1 d . . . . .
H18 H 1.0805 -0.2101 0.5954 0.074 Uiso 1 1 calc R U . . .
C19 C 0.9153(4) -0.11923(15) 0.59395(19) 0.0480(6) Uani 1 1 d . . . . .
H19 H 1.0120 -0.0904 0.5643 0.058 Uiso 1 1 calc R U . . .
N1 N 0.5987(4) 0.21307(12) 0.58782(18) 0.0554(6) Uani 1 1 d . . . . .
N2 N 0.6931(3) 0.15249(11) 0.60751(16) 0.0466(5) Uani 1 1 d . . . . .
N3 N 0.5524(3) 0.10635(10) 0.64249(14) 0.0343(4) Uani 1 1 d . . . . .
O1 O 0.7073(3) 0.12063(11) 1.11913(13) 0.0608(5) Uani 1 1 d . . . . .
O3 O 0.7369(3) 0.01267(10) 0.51340(13) 0.0496(5) Uani 1 1 d . . . . .
O2 O 0.1976(14) 0.0670(7) 0.7710(6) 0.056(3) Uani 0.56(2) 1 d D . P B 1
O2D O 0.1563(7) 0.1052(9) 0.7878(4) 0.047(3) Uani 0.44(2) 1 d D . P B 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
C1 O1 1.409(4) . ?
C2 O1 1.366(3) . ?
C2 C3 1.374(3) . ?
C2 C7 1.381(4) . ?
C3 C4 1.401(3) . ?
C4 C5 1.386(4) . ?
C4 C12 1.476(3) . ?
C5 C6 1.389(4) . ?
C5 O2D 1.395(5) . ?
C5 O2 1.449(6) . ?
C6 C7 1.362(4) . ?
C8 O2 1.355(5) . ?
C8 O2D 1.436(6) . ?
C8 C9 1.477(3) . ?
C9 N3 1.352(3) . ?
C9 C10 1.354(3) . ?
C10 N1 1.349(4) . ?
C11 C12 1.327(3) . ?
C11 N3 1.430(3) . ?
C11 C13 1.494(3) . ?
C13 O3 1.214(3) . ?
C13 C14 1.493(3) . ?
C14 C15 1.379(3) . ?
C14 C19 1.392(3) . ?
C15 C16 1.389(4) . ?
C16 C17 1.380(4) . ?
C17 C18 1.365(5) . ?
C18 C19 1.372(4) . ?
N1 N2 1.302(3) . ?
N2 N3 1.356(3) . ?

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 C2 C3 125.3(2) . . ?
O1 C2 C7 115.2(2) . . ?
C3 C2 C7 119.5(2) . . ?
C2 C3 C4 121.1(2) . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C12 124.4(2) . . ?
C3 C4 C12 117.0(2) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 O2D 139.9(5) . . ?
C6 C5 O2D 100.5(6) . . ?
C4 C5 O2 110.2(7) . . ?
C6 C5 O2 128.6(7) . . ?
C7 C6 C5 121.1(2) . . ?
C6 C7 C2 120.1(2) . . ?
O2 C8 C9 117.6(3) . . ?
O2D C8 C9 114.6(4) . . ?
N3 C9 C10 103.7(2) . . ?
N3 C9 C8 123.3(2) . . ?
C10 C9 C8 132.9(2) . . ?
N1 C10 C9 109.8(2) . . ?
C12 C11 N3 119.6(2) . . ?
C12 C11 C13 124.7(2) . . ?
N3 C11 C13 115.67(19) . . ?
C11 C12 C4 127.2(2) . . ?
O3 C13 C14 120.5(2) . . ?
O3 C13 C11 120.3(2) . . ?
C14 C13 C11 119.15(19) . . ?
C15 C14 C19 119.9(2) . . ?
C15 C14 C13 122.8(2) . . ?
C19 C14 C13 117.3(2) . . ?
C14 C15 C16 119.4(3) . . ?
C17 C16 C15 120.0(3) . . ?
C18 C17 C16 120.5(3) . . ?
C17 C18 C19 120.2(3) . . ?
C18 C19 C14 120.1(3) . . ?
N2 N1 C10 108.9(2) . . ?
N1 N2 N3 106.72(19) . . ?
C9 N3 N2 110.83(19) . . ?
C9 N3 C11 127.99(19) . . ?
N2 N3 C11 121.08(18) . . ?
C2 O1 C1 118.4(2) . . ?
C8 O2 C5 119.5(5) . . ?
C5 O2D C8 117.6(5) . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.037

