# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_6MeOPh
_database_code_depnum_ccdc_archive 'CCDC 1447749'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '6-p-Methoxyphenyl HPIP'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

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'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21'

_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'

_cell_length_a                   9.686(3)
_cell_length_b                   10.175(3)
_cell_length_c                   16.709(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.177(5)
_cell_angle_gamma                90
_cell_volume                     1609.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3874
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.997

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            16626
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0418
_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       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5856
_reflns_number_gt                4114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.992

_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

_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)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1294 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(7)
_chemical_absolute_configuration .
_refine_ls_number_reflns         5856
_refine_ls_number_parameters     443
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.4107(3) 0.7468(2) 0.18852(14) 0.0610(7) Uani 1 1 d . . . . .
H1 H -0.468(4) 0.733(4) 0.130(2) 0.099(14) Uiso 1 1 d . . . . .
C1 C -0.2866(3) 0.8113(3) 0.18725(19) 0.0456(8) Uani 1 1 d . . . . .
C2 C -0.1895(4) 0.8227(4) 0.2604(2) 0.0568(9) Uani 1 1 d . . . . .
H2 H -0.2104 0.7885 0.3081 0.068 Uiso 1 1 calc R U . . .
C3 C -0.0622(4) 0.8841(4) 0.2632(2) 0.0607(10) Uani 1 1 d . . . . .
H3 H 0.0028 0.8908 0.3127 0.073 Uiso 1 1 calc R U . . .
C4 C -0.0304(4) 0.9362(4) 0.1926(2) 0.0588(10) Uani 1 1 d . . . . .
H4 H 0.0557 0.9777 0.1942 0.071 Uiso 1 1 calc R U . . .
C5 C -0.1283(3) 0.9256(3) 0.1198(2) 0.0498(9) Uani 1 1 d . . . . .
H5 H -0.1070 0.9604 0.0724 0.060 Uiso 1 1 calc R U . . .
C6 C -0.2587(3) 0.8638(3) 0.11544(18) 0.0404(8) Uani 1 1 d . . . . .
C7 C -0.3625(3) 0.8555(3) 0.03775(18) 0.0405(8) Uani 1 1 d . . . . .
N1 N -0.4817(3) 0.7782(3) 0.03078(16) 0.0454(7) Uani 1 1 d . . . . .
C8 C -0.5525(3) 0.7900(3) -0.04658(19) 0.0433(8) Uani 1 1 d . . . . .
C9 C -0.6786(3) 0.7320(4) -0.0892(2) 0.0522(9) Uani 1 1 d . . . . .
H6 H -0.7292 0.6752 -0.0625 0.063 Uiso 1 1 calc R U . . .
C10 C -0.7256(3) 0.7600(3) -0.1703(2) 0.0523(9) Uani 1 1 d . . . . .
H7 H -0.8082 0.7205 -0.1987 0.063 Uiso 1 1 calc R U . . .
C11 C -0.6521(3) 0.8474(3) -0.21226(19) 0.0432(8) Uani 1 1 d . . . . .
C12 C -0.5311(3) 0.9040(3) -0.17052(18) 0.0445(8) Uani 1 1 d . . . . .
H8 H -0.4818 0.9625 -0.1969 0.053 Uiso 1 1 calc R U . . .
N2 N -0.4814(3) 0.8746(2) -0.08877(15) 0.0421(6) Uani 1 1 d . . . . .
C13 C -0.3609(3) 0.9161(3) -0.03558(17) 0.0439(8) Uani 1 1 d . . . . .
H9 H -0.2926 0.9733 -0.0469 0.053 Uiso 1 1 calc R U . . .
C14 C -0.7025(3) 0.8782(3) -0.30014(19) 0.0436(8) Uani 1 1 d . . . . .
C15 C -0.6988(3) 1.0057(3) -0.32772(18) 0.0451(8) Uani 1 1 d . . . . .
H10 H -0.6670 1.0718 -0.2899 0.054 Uiso 1 1 calc R U . . .
C16 C -0.7411(3) 1.0389(4) -0.40996(18) 0.0468(8) Uani 1 1 d . . . . .
H11 H -0.7391 1.1260 -0.4266 0.056 Uiso 1 1 calc R U . . .
C17 C -0.7859(3) 0.9411(4) -0.46642(19) 0.0513(9) Uani 1 1 d . . . . .
C18 C -0.7910(4) 0.8126(4) -0.4406(2) 0.0609(10) Uani 1 1 d . . . . .
H12 H -0.8216 0.7466 -0.4787 0.073 Uiso 1 1 calc R U . . .
C19 C -0.7510(4) 0.7816(4) -0.3588(2) 0.0590(10) Uani 1 1 d . . . . .
H13 H -0.7563 0.6948 -0.3422 0.071 Uiso 1 1 calc R U . . .
O2 O -0.8281(3) 0.9622(3) -0.54915(14) 0.0726(8) Uani 1 1 d . . . . .
C20 C -0.8276(5) 1.0938(5) -0.5779(2) 0.0953(16) Uani 1 1 d . . . . .
H14 H -0.7346 1.1302 -0.5609 0.114 Uiso 1 1 calc R U . . .
H15 H -0.8935 1.1454 -0.5557 0.114 Uiso 1 1 calc R U . . .
H16 H -0.8543 1.0946 -0.6366 0.114 Uiso 1 1 calc R U . . .
O3 O -0.0491(3) 0.7856(3) -0.12962(18) 0.0780(9) Uani 1 1 d . . . . .
H17 H 0.010(6) 0.758(6) -0.067(3) 0.18(2) Uiso 1 1 d . . . . .
C21 C -0.1678(4) 0.7100(4) -0.1416(2) 0.0523(9) Uani 1 1 d . . . . .
C22 C -0.2564(4) 0.7137(4) -0.2184(2) 0.0604(10) Uani 1 1 d . . . . .
H18 H -0.2342 0.7673 -0.2590 0.073 Uiso 1 1 calc R U . . .
C23 C -0.3774(4) 0.6382(4) -0.2349(2) 0.0639(10) Uani 1 1 d . . . . .
H19 H -0.4361 0.6404 -0.2867 0.077 Uiso 1 1 calc R U . . .
C24 C -0.4116(4) 0.5597(4) -0.1750(2) 0.0661(11) Uani 1 1 d . . . . .
H20 H -0.4932 0.5090 -0.1861 0.079 Uiso 1 1 calc R U . . .
C25 C -0.3233(4) 0.5567(4) -0.0978(2) 0.0550(9) Uani 1 1 d . . . . .
H21 H -0.3475 0.5041 -0.0574 0.066 Uiso 1 1 calc R U . . .
C26 C -0.1997(3) 0.6304(3) -0.0796(2) 0.0442(8) Uani 1 1 d . . . . .
C27 C -0.1072(3) 0.6251(3) 0.0013(2) 0.0433(8) Uani 1 1 d . . . . .
N3 N 0.0218(3) 0.6887(3) 0.01613(17) 0.0508(8) Uani 1 1 d . . . . .
C28 C 0.0811(3) 0.6664(3) 0.0942(2) 0.0469(8) Uani 1 1 d . . . . .
C29 C 0.2124(3) 0.7044(4) 0.1411(2) 0.0580(10) Uani 1 1 d . . . . .
H22 H 0.2727 0.7573 0.1186 0.070 Uiso 1 1 calc R U . . .
C30 C 0.2504(4) 0.6629(4) 0.2201(2) 0.0579(10) Uani 1 1 d . . . . .
H23 H 0.3376 0.6882 0.2513 0.070 Uiso 1 1 calc R U . . .
C31 C 0.1608(3) 0.5818(3) 0.2563(2) 0.0479(9) Uani 1 1 d . . . . .
C32 C 0.0327(3) 0.5479(3) 0.21006(19) 0.0463(8) Uani 1 1 d . . . . .
H24 H -0.0286 0.4961 0.2325 0.056 Uiso 1 1 calc R U . . .
N4 N -0.0064(3) 0.5900(3) 0.13032(16) 0.0432(7) Uani 1 1 d . . . . .
C33 C -0.1256(3) 0.5644(3) 0.0712(2) 0.0483(9) Uani 1 1 d . . . . .
H25 H -0.2036 0.5153 0.0776 0.058 Uiso 1 1 calc R U . . .
C34 C 0.2071(3) 0.5324(4) 0.34110(19) 0.0470(8) Uani 1 1 d . . . . .
C35 C 0.3472(4) 0.5022(4) 0.3717(2) 0.0638(11) Uani 1 1 d . . . . .
H26 H 0.4121 0.5158 0.3386 0.077 Uiso 1 1 calc R U . . .
C36 C 0.3947(4) 0.4525(4) 0.4495(2) 0.0649(11) Uani 1 1 d . . . . .
H27 H 0.4899 0.4331 0.4682 0.078 Uiso 1 1 calc R U . . .
C37 C 0.3012(4) 0.4320(4) 0.4988(2) 0.0575(9) Uani 1 1 d . . . . .
C38 C 0.1607(4) 0.4606(4) 0.4703(2) 0.0651(11) Uani 1 1 d . . . . .
H28 H 0.0966 0.4465 0.5037 0.078 Uiso 1 1 calc R U . . .
C39 C 0.1141(3) 0.5103(4) 0.3920(2) 0.0594(10) Uani 1 1 d . . . . .
H29 H 0.0187 0.5290 0.3735 0.071 Uiso 1 1 calc R U . . .
O4 O 0.3354(3) 0.3828(3) 0.57670(16) 0.0827(9) Uani 1 1 d . . . . .
C40 C 0.4798(4) 0.3594(5) 0.6114(2) 0.0959(16) Uani 1 1 d . . . . .
H30 H 0.4901 0.3359 0.6680 0.115 Uiso 1 1 calc R U . . .
H31 H 0.5334 0.4376 0.6072 0.115 Uiso 1 1 calc R U . . .
H32 H 0.5138 0.2891 0.5825 0.115 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.374(4) . ?
O1 H1 1.03(4) . ?
C1 C2 1.381(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(4) . ?
C7 C13 1.375(4) . ?
C7 N1 1.382(4) . ?
N1 C8 1.335(4) . ?
C8 N2 1.384(4) . ?
C8 C9 1.407(4) . ?
C9 C10 1.365(4) . ?
C9 H6 0.9300 . ?
C10 C11 1.414(4) . ?
C10 H7 0.9300 . ?
C11 C12 1.359(4) . ?
C11 C14 1.480(4) . ?
C12 N2 1.382(4) . ?
C12 H8 0.9300 . ?
N2 C13 1.376(4) . ?
C13 H9 0.9300 . ?
C14 C15 1.380(5) . ?
C14 C19 1.397(4) . ?
C15 C16 1.390(4) . ?
C15 H10 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H11 0.9300 . ?
C17 O2 1.373(4) . ?
C17 C18 1.381(5) . ?
C18 C19 1.377(4) . ?
C18 H12 0.9300 . ?
C19 H13 0.9300 . ?
O2 C20 1.424(5) . ?
C20 H14 0.9600 . ?
C20 H15 0.9600 . ?
C20 H16 0.9600 . ?
O3 C21 1.362(4) . ?
O3 H17 1.12(6) . ?
C21 C22 1.385(5) . ?
C21 C26 1.401(4) . ?
C22 C23 1.380(5) . ?
C22 H18 0.9300 . ?
C23 C24 1.374(5) . ?
C23 H19 0.9300 . ?
C24 C25 1.389(4) . ?
C24 H20 0.9300 . ?
C25 C26 1.391(4) . ?
C25 H21 0.9300 . ?
C26 C27 1.457(4) . ?
C27 C33 1.366(4) . ?
C27 N3 1.382(4) . ?
N3 C28 1.329(4) . ?
C28 N4 1.380(4) . ?
C28 C29 1.400(4) . ?
C29 C30 1.361(4) . ?
C29 H22 0.9300 . ?
C30 C31 1.422(5) . ?
C30 H23 0.9300 . ?
C31 C32 1.360(4) . ?
C31 C34 1.481(4) . ?
C32 N4 1.374(4) . ?
C32 H24 0.9300 . ?
N4 C33 1.377(4) . ?
C33 H25 0.9300 . ?
C34 C35 1.380(4) . ?
C34 C39 1.382(4) . ?
C35 C36 1.381(5) . ?
C35 H26 0.9300 . ?
C36 C37 1.362(4) . ?
C36 H27 0.9300 . ?
C37 O4 1.369(4) . ?
C37 C38 1.374(5) . ?
C38 C39 1.385(4) . ?
C38 H28 0.9300 . ?
C39 H29 0.9300 . ?
O4 C40 1.416(4) . ?
C40 H30 0.9600 . ?
C40 H31 0.9600 . ?
C40 H32 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
C1 O1 H1 110(2) . . ?
O1 C1 C2 117.5(3) . . ?
O1 C1 C6 121.8(3) . . ?
C2 C1 C6 120.7(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 121.3(3) . . ?
C5 C6 C7 121.0(3) . . ?
C13 C7 N1 110.3(3) . . ?
C13 C7 C6 128.9(3) . . ?
N1 C7 C6 120.8(3) . . ?
C8 N1 C7 106.2(2) . . ?
N1 C8 N2 109.9(3) . . ?
N1 C8 C9 131.8(3) . . ?
N2 C8 C9 118.3(3) . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H6 120.4 . . ?
C8 C9 H6 120.4 . . ?
C9 C10 C11 121.7(3) . . ?
C9 C10 H7 119.2 . . ?
C11 C10 H7 119.2 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 C14 119.2(3) . . ?
C10 C11 C14 122.0(3) . . ?
C11 C12 N2 119.9(3) . . ?
C11 C12 H8 120.1 . . ?
N2 C12 H8 120.1 . . ?
C13 N2 C12 130.0(3) . . ?
C13 N2 C8 107.9(2) . . ?
C12 N2 C8 122.1(3) . . ?
C7 C13 N2 105.7(3) . . ?
C7 C13 H9 127.1 . . ?
N2 C13 H9 127.1 . . ?
C15 C14 C19 117.1(3) . . ?
C15 C14 C11 120.3(3) . . ?
C19 C14 C11 122.6(3) . . ?
C14 C15 C16 122.4(3) . . ?
C14 C15 H10 118.8 . . ?
C16 C15 H10 118.8 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H11 120.4 . . ?
C15 C16 H11 120.4 . . ?
O2 C17 C16 124.1(3) . . ?
O2 C17 C18 116.0(3) . . ?
C16 C17 C18 119.8(3) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H12 119.8 . . ?
C17 C18 H12 119.8 . . ?
C18 C19 C14 121.2(3) . . ?
C18 C19 H13 119.4 . . ?
C14 C19 H13 119.4 . . ?
C17 O2 C20 117.7(3) . . ?
O2 C20 H14 109.5 . . ?
O2 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?
O2 C20 H16 109.5 . . ?
H14 C20 H16 109.5 . . ?
H15 C20 H16 109.5 . . ?
C21 O3 H17 104(3) . . ?
O3 C21 C22 117.4(3) . . ?
O3 C21 C26 121.9(3) . . ?
C22 C21 C26 120.7(3) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H18 119.9 . . ?
C21 C22 H18 119.9 . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H19 119.9 . . ?
C22 C23 H19 119.9 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H20 120.2 . . ?
C25 C24 H20 120.2 . . ?
C24 C25 C26 121.6(3) . . ?
C24 C25 H21 119.2 . . ?
C26 C25 H21 119.2 . . ?
C25 C26 C21 117.7(3) . . ?
C25 C26 C27 121.1(3) . . ?
C21 C26 C27 121.3(3) . . ?
C33 C27 N3 109.6(3) . . ?
C33 C27 C26 130.1(3) . . ?
N3 C27 C26 120.3(3) . . ?
C28 N3 C27 106.4(3) . . ?
N3 C28 N4 110.3(3) . . ?
N3 C28 C29 131.0(3) . . ?
N4 C28 C29 118.7(3) . . ?
C30 C29 C28 119.0(3) . . ?
C30 C29 H22 120.5 . . ?
C28 C29 H22 120.5 . . ?
C29 C30 C31 121.9(3) . . ?
C29 C30 H23 119.0 . . ?
C31 C30 H23 119.0 . . ?
C32 C31 C30 118.1(3) . . ?
C32 C31 C34 120.9(3) . . ?
C30 C31 C34 121.0(3) . . ?
C31 C32 N4 120.3(3) . . ?
C31 C32 H24 119.9 . . ?
N4 C32 H24 119.9 . . ?
C32 N4 C33 130.9(3) . . ?
C32 N4 C28 122.0(3) . . ?
C33 N4 C28 107.0(3) . . ?
C27 C33 N4 106.7(3) . . ?
C27 C33 H25 126.7 . . ?
N4 C33 H25 126.7 . . ?
C35 C34 C39 117.0(3) . . ?
C35 C34 C31 120.4(3) . . ?
C39 C34 C31 122.6(3) . . ?
C34 C35 C36 122.4(3) . . ?
C34 C35 H26 118.8 . . ?
C36 C35 H26 118.8 . . ?
C37 C36 C35 119.6(3) . . ?
C37 C36 H27 120.2 . . ?
C35 C36 H27 120.2 . . ?
C36 C37 O4 124.9(3) . . ?
C36 C37 C38 119.6(3) . . ?
O4 C37 C38 115.6(3) . . ?
C37 C38 C39 120.5(3) . . ?
C37 C38 H28 119.8 . . ?
C39 C38 H28 119.8 . . ?
C34 C39 C38 121.0(3) . . ?
C34 C39 H29 119.5 . . ?
C38 C39 H29 119.5 . . ?
C37 O4 C40 118.1(3) . . ?
O4 C40 H30 109.5 . . ?
O4 C40 H31 109.5 . . ?
H30 C40 H31 109.5 . . ?
O4 C40 H32 109.5 . . ?
H30 C40 H32 109.5 . . ?
H31 C40 H32 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 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
O1 C1 C6 C5 -178.8(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
O1 C1 C6 C7 1.5(5) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C1 C6 C7 C13 170.4(3) . . . . ?
C5 C6 C7 C13 -9.3(5) . . . . ?
C1 C6 C7 N1 -10.0(4) . . . . ?
C5 C6 C7 N1 170.4(3) . . . . ?
C13 C7 N1 C8 0.6(3) . . . . ?
C6 C7 N1 C8 -179.1(3) . . . . ?
C7 N1 C8 N2 -0.6(3) . . . . ?
C7 N1 C8 C9 178.2(3) . . . . ?
N1 C8 C9 C10 -178.3(3) . . . . ?
N2 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 -1.0(5) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C9 C10 C11 C14 180.0(3) . . . . ?
C10 C11 C12 N2 0.7(5) . . . . ?
C14 C11 C12 N2 -178.9(3) . . . . ?
C11 C12 N2 C13 177.8(3) . . . . ?
C11 C12 N2 C8 -1.2(4) . . . . ?
N1 C8 N2 C13 0.5(3) . . . . ?
C9 C8 N2 C13 -178.5(3) . . . . ?
N1 C8 N2 C12 179.6(3) . . . . ?
C9 C8 N2 C12 0.6(4) . . . . ?
N1 C7 C13 N2 -0.3(3) . . . . ?
C6 C7 C13 N2 179.4(3) . . . . ?
C12 N2 C13 C7 -179.2(3) . . . . ?
C8 N2 C13 C7 -0.1(3) . . . . ?
C12 C11 C14 C15 -42.8(4) . . . . ?
C10 C11 C14 C15 137.6(3) . . . . ?
C12 C11 C14 C19 135.1(3) . . . . ?
C10 C11 C14 C19 -44.4(5) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C11 C14 C15 C16 178.1(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 O2 -179.1(3) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
O2 C17 C18 C19 -179.9(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C14 -1.0(5) . . . . ?
C15 C14 C19 C18 1.1(5) . . . . ?
C11 C14 C19 C18 -176.9(3) . . . . ?
C16 C17 O2 C20 -1.1(5) . . . . ?
C18 C17 O2 C20 178.5(4) . . . . ?
O3 C21 C22 C23 179.2(3) . . . . ?
C26 C21 C22 C23 -0.3(5) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
C23 C24 C25 C26 -0.7(5) . . . . ?
C24 C25 C26 C21 1.0(5) . . . . ?
C24 C25 C26 C27 -179.3(3) . . . . ?
O3 C21 C26 C25 -179.9(3) . . . . ?
C22 C21 C26 C25 -0.5(5) . . . . ?
O3 C21 C26 C27 0.3(5) . . . . ?
C22 C21 C26 C27 179.7(3) . . . . ?
C25 C26 C27 C33 -6.6(5) . . . . ?
C21 C26 C27 C33 173.2(3) . . . . ?
C25 C26 C27 N3 173.7(3) . . . . ?
C21 C26 C27 N3 -6.6(5) . . . . ?
C33 C27 N3 C28 0.2(4) . . . . ?
C26 C27 N3 C28 180.0(3) . . . . ?
C27 N3 C28 N4 -0.1(3) . . . . ?
C27 N3 C28 C29 178.3(4) . . . . ?
N3 C28 C29 C30 -177.1(3) . . . . ?
N4 C28 C29 C30 1.2(5) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C29 C30 C31 C32 -1.2(5) . . . . ?
C29 C30 C31 C34 177.0(3) . . . . ?
C30 C31 C32 N4 0.9(5) . . . . ?
C34 C31 C32 N4 -177.2(3) . . . . ?
C31 C32 N4 C33 176.8(3) . . . . ?
C31 C32 N4 C28 0.4(5) . . . . ?
N3 C28 N4 C32 177.1(3) . . . . ?
C29 C28 N4 C32 -1.5(5) . . . . ?
N3 C28 N4 C33 -0.1(3) . . . . ?
C29 C28 N4 C33 -178.7(3) . . . . ?
N3 C27 C33 N4 -0.2(4) . . . . ?
C26 C27 C33 N4 180.0(3) . . . . ?
C32 N4 C33 C27 -176.7(3) . . . . ?
C28 N4 C33 C27 0.2(3) . . . . ?
C32 C31 C34 C35 144.4(4) . . . . ?
C30 C31 C34 C35 -33.8(5) . . . . ?
C32 C31 C34 C39 -33.5(5) . . . . ?
C30 C31 C34 C39 148.4(4) . . . . ?
C39 C34 C35 C36 -0.2(6) . . . . ?
C31 C34 C35 C36 -178.2(4) . . . . ?
C34 C35 C36 C37 -0.1(6) . . . . ?
C35 C36 C37 O4 179.7(4) . . . . ?
C35 C36 C37 C38 0.3(6) . . . . ?
C36 C37 C38 C39 -0.2(6) . . . . ?
O4 C37 C38 C39 -179.6(3) . . . . ?
C35 C34 C39 C38 0.3(5) . . . . ?
C31 C34 C39 C38 178.2(3) . . . . ?
C37 C38 C39 C34 -0.1(6) . . . . ?
C36 C37 O4 C40 4.6(6) . . . . ?
C38 C37 O4 C40 -176.0(4) . . . . ?

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
O1 H1 N1 1.03(4) 1.70(4) 2.599(3) 144(3) .
O3 H17 N3 1.12(6) 1.54(6) 2.582(4) 152(5) .

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_6MeOCOPh
_database_code_depnum_ccdc_archive 'CCDC 1447750'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '6-p-Methoxycarbonylphenyl HPIP'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.240(1)
_cell_length_b                   12.113(1)
_cell_length_c                   13.506(1)
_cell_angle_alpha                100.474(2)
_cell_angle_beta                 103.159(2)
_cell_angle_gamma                104.477(2)
_cell_volume                     1677.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    17108
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      73.34

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.7834
_exptl_absorpt_correction_T_max  0.8516
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         NONE
_diffrn_standards_interval_count NONE
_diffrn_standards_interval_time  NONE
_diffrn_standards_decay_%        NONE
_diffrn_reflns_number            17108
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         73.34
_reflns_number_total             6199
_reflns_number_gt                5502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MacScience Xpress'
_computing_cell_refinement       Scalepack
_computing_data_reduction        'Denzo and Scalepack'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    maXus
_computing_publication_material  ?

_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)+(0.0783P)²+0.9643P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6199
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.3096(2) 0.23240(19) -0.13390(17) 0.0835(6) Uani 1 1 d . . .
H1 H 0.3508 0.2412 -0.0730 0.125 Uiso 1 1 calc R . .
C1 C 0.2660(3) 0.3268(2) -0.1412(2) 0.0619(6) Uani 1 1 d . . .
C2 C 0.1896(3) 0.3242(3) -0.2381(2) 0.0733(8) Uani 1 1 d . . .
H2 H 0.1689 0.2591 -0.2944 0.088 Uiso 1 1 calc R . .
C3 C 0.1437(3) 0.4173(3) -0.2517(3) 0.0756(8) Uani 1 1 d . . .
H3 H 0.0930 0.4153 -0.3172 0.091 Uiso 1 1 calc R . .
C4 C 0.1729(3) 0.5133(3) -0.1683(3) 0.0738(8) Uani 1 1 d . . .
H4 H 0.1414 0.5760 -0.1772 0.089 Uiso 1 1 calc R . .
C5 C 0.2489(3) 0.5162(3) -0.0718(2) 0.0669(7) Uani 1 1 d . . .
H5 H 0.2682 0.5815 -0.0159 0.080 Uiso 1 1 calc R . .
C6 C 0.2978(2) 0.4235(2) -0.0556(2) 0.0559(6) Uani 1 1 d . . .
C7 C 0.3792(2) 0.4293(2) 0.0478(2) 0.0534(6) Uani 1 1 d . . .
N1 N 0.4253(2) 0.33691(19) 0.06487(17) 0.0569(5) Uani 1 1 d . . .
C8 C 0.4935(2) 0.3684(2) 0.16472(19) 0.0535(6) Uani 1 1 d . . .
C9 C 0.5630(3) 0.3109(2) 0.2266(2) 0.0587(6) Uani 1 1 d . . .
H6 H 0.5666 0.2366 0.1970 0.070 Uiso 1 1 calc R . .
C10 C 0.6244(3) 0.3638(2) 0.3291(2) 0.0571(6) Uani 1 1 d . . .
H7 H 0.6693 0.3246 0.3695 0.069 Uiso 1 1 calc R . .
C11 C 0.6224(2) 0.4778(2) 0.3771(2) 0.0539(6) Uani 1 1 d . . .
C12 C 0.5569(3) 0.5340(2) 0.3166(2) 0.0567(6) Uani 1 1 d . . .
H8 H 0.5551 0.6091 0.3457 0.068 Uiso 1 1 calc R . .
N2 N 0.4936(2) 0.48027(17) 0.21305(16) 0.0527(5) Uani 1 1 d . . .
C13 C 0.4203(3) 0.5178(2) 0.1381(2) 0.0572(6) Uani 1 1 d . . .
H9 H 0.4022 0.5892 0.1469 0.069 Uiso 1 1 calc R . .
C14 C 0.6864(2) 0.5332(2) 0.4903(2) 0.0545(6) Uani 1 1 d . . .
C15 C 0.7882(3) 0.5021(3) 0.5460(2) 0.0656(7) Uani 1 1 d . . .
H10 H 0.8190 0.4469 0.5110 0.079 Uiso 1 1 calc R . .
C16 C 0.8438(3) 0.5517(3) 0.6518(2) 0.0667(7) Uani 1 1 d . . .
H11 H 0.9110 0.5290 0.6874 0.080 Uiso 1 1 calc R . .
C17 C 0.8011(2) 0.6354(2) 0.7065(2) 0.0576(6) Uani 1 1 d . . .
C18 C 0.7010(3) 0.6676(2) 0.6512(2) 0.0608(6) Uani 1 1 d . . .
H12 H 0.6722 0.7247 0.6859 0.073 Uiso 1 1 calc R . .
C19 C 0.6437(3) 0.6165(2) 0.5461(2) 0.0597(6) Uani 1 1 d . . .
H13 H 0.5749 0.6378 0.5112 0.072 Uiso 1 1 calc R . .
C20 C 0.8586(3) 0.6935(3) 0.8196(2) 0.0629(7) Uani 1 1 d . . .
O2 O 0.9398(2) 0.6424(2) 0.86693(16) 0.0803(6) Uani 1 1 d . . .
C21 C 1.0008(3) 0.6925(4) 0.9768(2) 0.0884(10) Uani 1 1 d . . .
H14 H 1.0521 0.7724 0.9879 0.133 Uiso 1 1 calc R . .
H15 H 1.0544 0.6476 1.0029 0.133 Uiso 1 1 calc R . .
H16 H 0.9367 0.6912 1.0133 0.133 Uiso 1 1 calc R . .
O3 O 0.8355(2) 0.7763(2) 0.86591(16) 0.0808(6) Uani 1 1 d . . .
O4 O 0.1251(2) -0.25966(19) -0.32887(16) 0.0753(6) Uani 1 1 d . . .
H17 H 0.1735 -0.2452 -0.2695 0.113 Uiso 1 1 calc R . .
C22 C 0.0650(3) -0.1753(3) -0.3343(2) 0.0637(7) Uani 1 1 d . . .
C23 C -0.0173(3) -0.1836(3) -0.4306(2) 0.0747(8) Uani 1 1 d . . .
H18 H -0.0295 -0.2451 -0.4880 0.090 Uiso 1 1 calc R . .
C24 C -0.0810(3) -0.1016(3) -0.4421(3) 0.0804(9) Uani 1 1 d . . .
H19 H -0.1365 -0.1080 -0.5069 0.096 Uiso 1 1 calc R . .
C25 C -0.0628(3) -0.0098(3) -0.3578(3) 0.0796(9) Uani 1 1 d . . .
H20 H -0.1052 0.0463 -0.3657 0.096 Uiso 1 1 calc R . .
C26 C 0.0183(3) -0.0017(3) -0.2622(3) 0.0746(8) Uani 1 1 d . . .
H21 H 0.0300 0.0606 -0.2056 0.090 Uiso 1 1 calc R . .
C27 C 0.0838(3) -0.0838(2) -0.2471(2) 0.0609(6) Uani 1 1 d . . .
C28 C 0.1697(3) -0.0727(2) -0.1438(2) 0.0601(6) Uani 1 1 d . . .
N3 N 0.2471(2) -0.1444(2) -0.13178(18) 0.0631(6) Uani 1 1 d . . .
C29 C 0.3127(3) -0.1123(2) -0.0310(2) 0.0571(6) Uani 1 1 d . . .
C30 C 0.4068(3) -0.1523(2) 0.0272(2) 0.0640(7) Uani 1 1 d . . .
H22 H 0.4326 -0.2125 -0.0062 0.077 Uiso 1 1 calc R . .
C31 C 0.4594(3) -0.1033(2) 0.1310(2) 0.0614(6) Uani 1 1 d . . .
H23 H 0.5221 -0.1298 0.1685 0.074 Uiso 1 1 calc R . .
C32 C 0.4208(2) -0.0116(2) 0.1847(2) 0.0548(6) Uani 1 1 d . . .
C33 C 0.3302(3) 0.0271(2) 0.1285(2) 0.0593(6) Uani 1 1 d . . .
H24 H 0.3041 0.0870 0.1618 0.071 Uiso 1 1 calc R . .
N4 N 0.2776(2) -0.02246(18) 0.02289(16) 0.0569(5) Uani 1 1 d . . .
C34 C 0.1868(3) 0.0020(3) -0.0495(2) 0.0641(7) Uani 1 1 d . . .
H25 H 0.1452 0.0582 -0.0368 0.077 Uiso 1 1 calc R . .
C35 C 0.4792(3) 0.0421(2) 0.2987(2) 0.0552(6) Uani 1 1 d . . .
C36 C 0.6080(3) 0.0608(2) 0.3463(2) 0.0594(6) Uani 1 1 d . . .
H26 H 0.6580 0.0353 0.3064 0.071 Uiso 1 1 calc R . .
C37 C 0.6636(3) 0.1163(2) 0.4517(2) 0.0588(6) Uani 1 1 d . . .
H27 H 0.7502 0.1280 0.4820 0.071 Uiso 1 1 calc R . .
C38 C 0.5902(3) 0.1549(2) 0.5127(2) 0.0567(6) Uani 1 1 d . . .
C39 C 0.4604(3) 0.1337(2) 0.4664(2) 0.0589(6) Uani 1 1 d . . .
H28 H 0.4098 0.1569 0.5068 0.071 Uiso 1 1 calc R . .
C40 C 0.4059(3) 0.0787(2) 0.3613(2) 0.0599(6) Uani 1 1 d . . .
H29 H 0.3189 0.0656 0.3314 0.072 Uiso 1 1 calc R . .
C41 C 0.6445(3) 0.2163(2) 0.6257(2) 0.0631(7) Uani 1 1 d . . .
O5 O 0.7667(2) 0.2225(2) 0.66335(15) 0.0781(6) Uani 1 1 d . . .
C42 C 0.8252(4) 0.2779(4) 0.7735(2) 0.0930(11) Uani 1 1 d . . .
H30 H 0.7775 0.2371 0.8135 0.140 Uiso 1 1 calc R . .
H31 H 0.8254 0.3586 0.7874 0.140 Uiso 1 1 calc R . .
H32 H 0.9118 0.2750 0.7930 0.140 Uiso 1 1 calc R . .
O6 O 0.5847(2) 0.2562(2) 0.67918(16) 0.0805(6) 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
O1 C1 1.363(3) . ?
O1 H1 0.8200 . ?
C1 C2 1.382(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(4) . ?
C7 C13 1.367(4) . ?
C7 N1 1.379(3) . ?
N1 C8 1.322(3) . ?
C8 N2 1.392(3) . ?
C8 C9 1.408(3) . ?
C9 C10 1.351(4) . ?
C9 H6 0.9300 . ?
C10 C11 1.423(3) . ?
C10 H7 0.9300 . ?
C11 C12 1.361(3) . ?
C11 C14 1.479(3) . ?
C12 N2 1.367(3) . ?
C12 H8 0.9300 . ?
N2 C13 1.373(3) . ?
C13 H9 0.9300 . ?
C14 C15 1.394(4) . ?
C14 C19 1.396(4) . ?
C15 C16 1.374(4) . ?
C15 H10 0.9300 . ?
C16 C17 1.391(4) . ?
C16 H11 0.9300 . ?
C17 C18 1.386(4) . ?
C17 C20 1.475(4) . ?
C18 C19 1.370(4) . ?
C18 H12 0.9300 . ?
C19 H13 0.9300 . ?
C20 O3 1.200(3) . ?
C20 O2 1.336(3) . ?
O2 C21 1.429(3) . ?
C21 H14 0.9600 . ?
C21 H15 0.9600 . ?
C21 H16 0.9600 . ?
O4 C22 1.363(3) . ?
O4 H17 0.8200 . ?
C22 C23 1.384(4) . ?
C22 C27 1.399(4) . ?
C23 C24 1.372(5) . ?
C23 H18 0.9300 . ?
C24 C25 1.376(5) . ?
C24 H19 0.9300 . ?
C25 C26 1.372(4) . ?
C25 H20 0.9300 . ?
C26 C27 1.395(4) . ?
C26 H21 0.9300 . ?
C27 C28 1.467(4) . ?
C28 C34 1.363(4) . ?
C28 N3 1.379(3) . ?
N3 C29 1.325(3) . ?
C29 N4 1.389(3) . ?
C29 C30 1.409(4) . ?
C30 C31 1.347(4) . ?
C30 H22 0.9300 . ?
C31 C32 1.428(4) . ?
C31 H23 0.9300 . ?
C32 C33 1.359(4) . ?
C32 C35 1.479(4) . ?
C33 N4 1.369(3) . ?
C33 H24 0.9300 . ?
N4 C34 1.374(3) . ?
C34 H25 0.9300 . ?
C35 C36 1.386(4) . ?
C35 C40 1.397(4) . ?
C36 C37 1.380(4) . ?
C36 H26 0.9300 . ?
C37 C38 1.393(4) . ?
C37 H27 0.9300 . ?
C38 C39 1.387(4) . ?
C38 C41 1.481(4) . ?
C39 C40 1.375(4) . ?
C39 H28 0.9300 . ?
C40 H29 0.9300 . ?
C41 O6 1.210(3) . ?
C41 O5 1.329(3) . ?
O5 C42 1.437(4) . ?
C42 H30 0.9600 . ?
C42 H31 0.9600 . ?
C42 H32 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 117.3(3) . . ?
O1 C1 C6 122.0(2) . . ?
C2 C1 C6 120.7(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C7 120.5(2) . . ?
C13 C7 N1 110.3(2) . . ?
C13 C7 C6 129.0(2) . . ?
N1 C7 C6 120.7(2) . . ?
C8 N1 C7 106.0(2) . . ?
N1 C8 N2 110.6(2) . . ?
N1 C8 C9 132.0(2) . . ?
N2 C8 C9 117.4(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H6 120.1 . . ?
C8 C9 H6 120.1 . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H7 119.1 . . ?
C11 C10 H7 119.1 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 C14 120.5(2) . . ?
C10 C11 C14 121.3(2) . . ?
C11 C12 N2 120.2(2) . . ?
C11 C12 H8 119.9 . . ?
N2 C12 H8 119.9 . . ?
C12 N2 C13 130.6(2) . . ?
C12 N2 C8 122.6(2) . . ?
C13 N2 C8 106.7(2) . . ?
C7 C13 N2 106.3(2) . . ?
C7 C13 H9 126.8 . . ?
N2 C13 H9 126.8 . . ?
C15 C14 C19 117.4(2) . . ?
C15 C14 C11 121.9(2) . . ?
C19 C14 C11 120.7(2) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H10 119.5 . . ?
C14 C15 H10 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H11 119.5 . . ?
C17 C16 H11 119.5 . . ?
C18 C17 C16 118.1(2) . . ?
C18 C17 C20 118.3(2) . . ?
C16 C17 C20 123.6(2) . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H12 119.6 . . ?
C17 C18 H12 119.6 . . ?
C18 C19 C14 121.5(2) . . ?
C18 C19 H13 119.3 . . ?
C14 C19 H13 119.3 . . ?
O3 C20 O2 122.6(3) . . ?
O3 C20 C17 125.1(3) . . ?
O2 C20 C17 112.3(2) . . ?
C20 O2 C21 116.6(2) . . ?
O2 C21 H14 109.5 . . ?
O2 C21 H15 109.5 . . ?
H14 C21 H15 109.5 . . ?
O2 C21 H16 109.5 . . ?
H14 C21 H16 109.5 . . ?
H15 C21 H16 109.5 . . ?
C22 O4 H17 109.5 . . ?
O4 C22 C23 117.2(3) . . ?
O4 C22 C27 122.2(2) . . ?
C23 C22 C27 120.5(3) . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H18 119.8 . . ?
C22 C23 H18 119.8 . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H19 119.9 . . ?
C25 C24 H19 119.9 . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H20 120.2 . . ?
C24 C25 H20 120.2 . . ?
C25 C26 C27 122.1(3) . . ?
C25 C26 H21 119.0 . . ?
C27 C26 H21 119.0 . . ?
C26 C27 C22 117.3(3) . . ?
C26 C27 C28 120.7(3) . . ?
C22 C27 C28 122.0(3) . . ?
C34 C28 N3 110.3(2) . . ?
C34 C28 C27 129.0(3) . . ?
N3 C28 C27 120.7(2) . . ?
C29 N3 C28 106.1(2) . . ?
N3 C29 N4 110.3(2) . . ?
N3 C29 C30 132.2(2) . . ?
N4 C29 C30 117.5(2) . . ?
C31 C30 C29 120.1(2) . . ?
C31 C30 H22 120.0 . . ?
C29 C30 H22 120.0 . . ?
C30 C31 C32 121.2(2) . . ?
C30 C31 H23 119.4 . . ?
C32 C31 H23 119.4 . . ?
C33 C32 C31 118.7(2) . . ?
C33 C32 C35 120.3(2) . . ?
C31 C32 C35 121.1(2) . . ?
C32 C33 N4 119.9(2) . . ?
C32 C33 H24 120.1 . . ?
N4 C33 H24 120.1 . . ?
C33 N4 C34 130.4(2) . . ?
C33 N4 C29 122.6(2) . . ?
C34 N4 C29 106.9(2) . . ?
C28 C34 N4 106.3(2) . . ?
C28 C34 H25 126.9 . . ?
N4 C34 H25 126.9 . . ?
C36 C35 C40 117.9(2) . . ?
C36 C35 C32 121.5(2) . . ?
C40 C35 C32 120.5(2) . . ?
C37 C36 C35 121.4(2) . . ?
C37 C36 H26 119.3 . . ?
C35 C36 H26 119.3 . . ?
C36 C37 C38 120.2(3) . . ?
C36 C37 H27 119.9 . . ?
C38 C37 H27 119.9 . . ?
C39 C38 C37 118.9(2) . . ?
C39 C38 C41 118.3(2) . . ?
C37 C38 C41 122.7(3) . . ?
C40 C39 C38 120.5(2) . . ?
C40 C39 H28 119.8 . . ?
C38 C39 H28 119.8 . . ?
C39 C40 C35 121.1(3) . . ?
C39 C40 H29 119.4 . . ?
C35 C40 H29 119.4 . . ?
O6 C41 O5 123.0(3) . . ?
O6 C41 C38 124.1(3) . . ?
O5 C41 C38 112.9(2) . . ?
C41 O5 C42 116.2(2) . . ?
O5 C42 H30 109.5 . . ?
O5 C42 H31 109.5 . . ?
H30 C42 H31 109.5 . . ?
O5 C42 H32 109.5 . . ?
H30 C42 H32 109.5 . . ?
H31 C42 H32 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 C2 C3 -179.0(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
O1 C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
O1 C1 C6 C7 -0.5(4) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C1 C6 C7 C13 178.8(3) . . . . ?
C5 C6 C7 C13 -1.1(4) . . . . ?
C1 C6 C7 N1 -1.6(4) . . . . ?
C5 C6 C7 N1 178.5(2) . . . . ?
C13 C7 N1 C8 0.3(3) . . . . ?
C6 C7 N1 C8 -179.4(2) . . . . ?
C7 N1 C8 N2 -0.5(3) . . . . ?
C7 N1 C8 C9 180.0(3) . . . . ?
N1 C8 C9 C10 -179.4(3) . . . . ?
N2 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C9 C10 C11 C14 177.9(2) . . . . ?
C10 C11 C12 N2 1.0(4) . . . . ?
C14 C11 C12 N2 -177.4(2) . . . . ?
C11 C12 N2 C13 178.6(3) . . . . ?
C11 C12 N2 C8 -0.5(4) . . . . ?
N1 C8 N2 C12 179.9(2) . . . . ?
C9 C8 N2 C12 -0.5(4) . . . . ?
N1 C8 N2 C13 0.5(3) . . . . ?
C9 C8 N2 C13 -179.9(2) . . . . ?
N1 C7 C13 N2 0.1(3) . . . . ?
C6 C7 C13 N2 179.7(2) . . . . ?
C12 N2 C13 C7 -179.6(2) . . . . ?
C8 N2 C13 C7 -0.3(3) . . . . ?
C12 C11 C14 C15 -157.1(3) . . . . ?
C10 C11 C14 C15 24.5(4) . . . . ?
C12 C11 C14 C19 24.9(4) . . . . ?
C10 C11 C14 C19 -153.4(3) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
C11 C14 C15 C16 -177.9(3) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C15 C16 C17 C20 -178.7(3) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C20 C17 C18 C19 -179.9(3) . . . . ?
C17 C18 C19 C14 -2.0(4) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C11 C14 C19 C18 179.2(2) . . . . ?
C18 C17 C20 O3 -8.7(4) . . . . ?
C16 C17 C20 O3 169.9(3) . . . . ?
C18 C17 C20 O2 170.3(2) . . . . ?
C16 C17 C20 O2 -11.1(4) . . . . ?
O3 C20 O2 C21 -1.1(4) . . . . ?
C17 C20 O2 C21 179.9(3) . . . . ?
O4 C22 C23 C24 -179.8(3) . . . . ?
C27 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C23 C24 C25 C26 -0.7(5) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C25 C26 C27 C22 0.8(5) . . . . ?
C25 C26 C27 C28 -179.9(3) . . . . ?
O4 C22 C27 C26 179.3(3) . . . . ?
C23 C22 C27 C26 -1.0(4) . . . . ?
O4 C22 C27 C28 -0.1(4) . . . . ?
C23 C22 C27 C28 179.7(3) . . . . ?
C26 C27 C28 C34 9.2(5) . . . . ?
C22 C27 C28 C34 -171.5(3) . . . . ?
C26 C27 C28 N3 -171.5(3) . . . . ?
C22 C27 C28 N3 7.8(4) . . . . ?
C34 C28 N3 C29 -1.0(3) . . . . ?
C27 C28 N3 C29 179.5(2) . . . . ?
C28 N3 C29 N4 1.0(3) . . . . ?
C28 N3 C29 C30 -179.1(3) . . . . ?
N3 C29 C30 C31 179.9(3) . . . . ?
N4 C29 C30 C31 -0.2(4) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C31 C32 C33 -0.8(4) . . . . ?
C30 C31 C32 C35 -179.8(3) . . . . ?
C31 C32 C33 N4 0.4(4) . . . . ?
C35 C32 C33 N4 179.4(2) . . . . ?
C32 C33 N4 C34 -179.4(3) . . . . ?
C32 C33 N4 C29 0.1(4) . . . . ?
N3 C29 N4 C33 179.7(2) . . . . ?
C30 C29 N4 C33 -0.2(4) . . . . ?
N3 C29 N4 C34 -0.7(3) . . . . ?
C30 C29 N4 C34 179.4(3) . . . . ?
N3 C28 C34 N4 0.6(3) . . . . ?
C27 C28 C34 N4 -180.0(3) . . . . ?
C33 N4 C34 C28 179.6(3) . . . . ?
C29 N4 C34 C28 0.0(3) . . . . ?
C33 C32 C35 C36 -142.3(3) . . . . ?
C31 C32 C35 C36 36.8(4) . . . . ?
C33 C32 C35 C40 36.0(4) . . . . ?
C31 C32 C35 C40 -145.0(3) . . . . ?
C40 C35 C36 C37 -1.6(4) . . . . ?
C32 C35 C36 C37 176.7(2) . . . . ?
C35 C36 C37 C38 0.1(4) . . . . ?
C36 C37 C38 C39 1.7(4) . . . . ?
C36 C37 C38 C41 -179.2(2) . . . . ?
C37 C38 C39 C40 -2.0(4) . . . . ?
C41 C38 C39 C40 178.9(2) . . . . ?
C38 C39 C40 C35 0.4(4) . . . . ?
C36 C35 C40 C39 1.4(4) . . . . ?
C32 C35 C40 C39 -176.9(2) . . . . ?
C39 C38 C41 O6 -5.0(4) . . . . ?
C37 C38 C41 O6 175.9(3) . . . . ?
C39 C38 C41 O5 174.5(2) . . . . ?
C37 C38 C41 O5 -4.6(4) . . . . ?
O6 C41 O5 C42 1.3(4) . . . . ?
C38 C41 O5 C42 -178.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_8MeOCOPh
_database_code_depnum_ccdc_archive 'CCDC 1447751'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '8-p-Methoxycarbonylphenyl HPIP'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   12.846(1)
_cell_length_b                   17.232(1)
_cell_length_c                   7.549(1)
_cell_angle_alpha                90
_cell_angle_beta                 96.393(1)
_cell_angle_gamma                90
_cell_volume                     1660.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15853
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      73.29

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.760
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8098
_exptl_absorpt_correction_T_max  0.8957
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4356
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.462
_diffrn_reflns_theta_max         73.292
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3245
_reflns_number_gt                3019
_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       'MacScience Xpress'
_computing_cell_refinement       Scalepack
_computing_data_reduction        'Denzo and Scalepack'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    maXus
_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)+(0.0749P)²+0.5363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3245
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58199(12) 0.22572(8) 0.0037(2) 0.0616(4) Uani 1 1 d . . . . .
H1 H 0.535(2) 0.1927(18) 0.064(4) 0.092 Uiso 1 1 d . U . . .
C1 C 0.67381(15) 0.18750(11) -0.0014(2) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.75211(17) 0.22448(12) -0.0825(3) 0.0586(5) Uani 1 1 d . . . . .
H2 H 0.7401 0.2738 -0.1306 0.070 Uiso 1 1 calc R U . . .
C3 C 0.84696(18) 0.18908(14) -0.0924(3) 0.0679(6) Uani 1 1 d . . . . .
H3 H 0.8985 0.2142 -0.1482 0.082 Uiso 1 1 calc R U . . .
C4 C 0.86616(17) 0.11602(14) -0.0194(3) 0.0682(6) Uani 1 1 d . . . . .
H4 H 0.9307 0.0923 -0.0247 0.082 Uiso 1 1 calc R U . . .
C5 C 0.78904(15) 0.07885(12) 0.0611(3) 0.0569(5) Uani 1 1 d . . . . .
H5 H 0.8024 0.0299 0.1101 0.068 Uiso 1 1 calc R U . . .
C6 C 0.69132(14) 0.11284(10) 0.0711(2) 0.0458(4) Uani 1 1 d . . . . .
C7 C 0.60835(14) 0.07083(10) 0.1478(2) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.51416(11) 0.10615(8) 0.16654(19) 0.0449(3) Uani 1 1 d . . . . .
C8 C 0.45570(14) 0.05343(9) 0.2380(2) 0.0435(4) Uani 1 1 d . . . . .
C9 C 0.35281(14) 0.05808(10) 0.2862(2) 0.0457(4) Uani 1 1 d . . . . .
C10 C 0.31172(16) -0.00741(11) 0.3566(3) 0.0534(4) Uani 1 1 d . . . . .
H6 H 0.2442 -0.0059 0.3899 0.064 Uiso 1 1 calc R U . . .
C11 C 0.37031(17) -0.07675(11) 0.3792(3) 0.0568(5) Uani 1 1 d . . . . .
H7 H 0.3406 -0.1203 0.4264 0.068 Uiso 1 1 calc R U . . .
C12 C 0.46821(17) -0.08075(10) 0.3335(2) 0.0548(5) Uani 1 1 d . . . . .
H8 H 0.5064 -0.1266 0.3487 0.066 Uiso 1 1 calc R U . . .
N2 N 0.51121(12) -0.01578(8) 0.26355(19) 0.0465(4) Uani 1 1 d . . . . .
C13 C 0.60753(15) -0.00428(10) 0.2072(2) 0.0495(4) Uani 1 1 d . . . . .
H9 H 0.6616 -0.0402 0.2089 0.059 Uiso 1 1 calc R U . . .
C14 C 0.29258(14) 0.13103(10) 0.2573(2) 0.0459(4) Uani 1 1 d . . . . .
C15 C 0.18739(15) 0.12888(11) 0.1899(3) 0.0536(5) Uani 1 1 d . . . . .
H10 H 0.1550 0.0812 0.1654 0.064 Uiso 1 1 calc R U . . .
C16 C 0.13011(15) 0.19619(11) 0.1587(3) 0.0551(5) Uani 1 1 d . . . . .
H11 H 0.0600 0.1936 0.1126 0.066 Uiso 1 1 calc R U . . .
C17 C 0.17696(14) 0.26781(10) 0.1959(2) 0.0476(4) Uani 1 1 d . . . . .
C18 C 0.28095(15) 0.27038(10) 0.2674(3) 0.0524(4) Uani 1 1 d . . . . .
H12 H 0.3123 0.3180 0.2961 0.063 Uiso 1 1 calc R U . . .
C19 C 0.33872(14) 0.20305(10) 0.2965(3) 0.0511(4) Uani 1 1 d . . . . .
H13 H 0.4088 0.2058 0.3426 0.061 Uiso 1 1 calc R U . . .
C20 C 0.11919(15) 0.34125(11) 0.1544(3) 0.0540(5) Uani 1 1 d . . . . .
O2 O 0.02250(11) 0.32896(8) 0.0762(2) 0.0685(4) Uani 1 1 d . . . . .
C21 C -0.0388(2) 0.39577(14) 0.0199(5) 0.0845(8) Uani 1 1 d . . . . .
H14 H -0.0420 0.4301 0.1193 0.127 Uiso 1 1 calc R U . . .
H15 H -0.1084 0.3798 -0.0249 0.127 Uiso 1 1 calc R U . . .
H16 H -0.0072 0.4222 -0.0724 0.127 Uiso 1 1 calc R U . . .
O3 O 0.15454(14) 0.40518(8) 0.1844(3) 0.0823(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
O1 C1 1.355(2) . ?
O1 H1 0.98(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(3) . ?
C7 C13 1.370(2) . ?
C7 N1 1.376(2) . ?
N1 C8 1.331(2) . ?
C8 N2 1.392(2) . ?
C8 C9 1.412(3) . ?
C9 C10 1.378(2) . ?
C9 C14 1.479(2) . ?
C10 C11 1.412(3) . ?
C10 H6 0.9300 . ?
C11 C12 1.342(3) . ?
C11 H7 0.9300 . ?
C12 N2 1.379(2) . ?
C12 H8 0.9300 . ?
N2 C13 1.367(2) . ?
C13 H9 0.9300 . ?
C14 C15 1.390(3) . ?
C14 C19 1.393(2) . ?
C15 C16 1.380(3) . ?
C15 H10 0.9300 . ?
C16 C17 1.388(2) . ?
C16 H11 0.9300 . ?
C17 C18 1.385(3) . ?
C17 C20 1.483(3) . ?
C18 C19 1.381(3) . ?
C18 H12 0.9300 . ?
C19 H13 0.9300 . ?
C20 O3 1.203(2) . ?
C20 O2 1.331(2) . ?
O2 C21 1.433(3) . ?
C21 H14 0.9600 . ?
C21 H15 0.9600 . ?
C21 H16 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
C1 O1 H1 108.4(17) . . ?
O1 C1 C2 117.70(17) . . ?
O1 C1 C6 122.38(17) . . ?
C2 C1 C6 119.92(18) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.96(18) . . ?
C5 C6 C7 120.95(17) . . ?
C1 C6 C7 121.04(16) . . ?
C13 C7 N1 110.21(16) . . ?
C13 C7 C6 129.09(17) . . ?
N1 C7 C6 120.70(15) . . ?
C8 N1 C7 106.39(14) . . ?
N1 C8 N2 109.73(15) . . ?
N1 C8 C9 130.73(16) . . ?
N2 C8 C9 119.54(15) . . ?
C10 C9 C8 117.57(17) . . ?
C10 C9 C14 122.44(17) . . ?
C8 C9 C14 119.98(15) . . ?
C9 C10 C11 121.18(19) . . ?
C9 C10 H6 119.4 . . ?
C11 C10 H6 119.4 . . ?
C12 C11 C10 120.96(18) . . ?
C12 C11 H7 119.5 . . ?
C10 C11 H7 119.5 . . ?
C11 C12 N2 118.90(17) . . ?
C11 C12 H8 120.5 . . ?
N2 C12 H8 120.5 . . ?
C13 N2 C12 130.68(16) . . ?
C13 N2 C8 107.47(14) . . ?
C12 N2 C8 121.85(17) . . ?
N2 C13 C7 106.20(15) . . ?
N2 C13 H9 126.9 . . ?
C7 C13 H9 126.9 . . ?
C15 C14 C19 118.34(17) . . ?
C15 C14 C9 120.16(16) . . ?
C19 C14 C9 121.50(16) . . ?
C16 C15 C14 121.21(17) . . ?
C16 C15 H10 119.4 . . ?
C14 C15 H10 119.4 . . ?
C15 C16 C17 120.13(18) . . ?
C15 C16 H11 119.9 . . ?
C17 C16 H11 119.9 . . ?
C18 C17 C16 119.01(17) . . ?
C18 C17 C20 119.58(16) . . ?
C16 C17 C20 121.37(17) . . ?
C19 C18 C17 120.87(16) . . ?
C19 C18 H12 119.6 . . ?
C17 C18 H12 119.6 . . ?
C18 C19 C14 120.40(17) . . ?
C18 C19 H13 119.8 . . ?
C14 C19 H13 119.8 . . ?
O3 C20 O2 122.87(19) . . ?
O3 C20 C17 124.89(19) . . ?
O2 C20 C17 112.23(16) . . ?
C20 O2 C21 117.32(18) . . ?
O2 C21 H14 109.5 . . ?
O2 C21 H15 109.5 . . ?
H14 C21 H15 109.5 . . ?
O2 C21 H16 109.5 . . ?
H14 C21 H16 109.5 . . ?
H15 C21 H16 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 C2 C3 -179.94(18) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 176.46(18) . . . . ?
O1 C1 C6 C5 -179.20(17) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
O1 C1 C6 C7 3.3(3) . . . . ?
C2 C1 C6 C7 -176.41(16) . . . . ?
C5 C6 C7 C13 -4.7(3) . . . . ?
C1 C6 C7 C13 172.70(17) . . . . ?
C5 C6 C7 N1 176.31(16) . . . . ?
C1 C6 C7 N1 -6.3(2) . . . . ?
C13 C7 N1 C8 0.38(19) . . . . ?
C6 C7 N1 C8 179.53(14) . . . . ?
C7 N1 C8 N2 -0.67(18) . . . . ?
C7 N1 C8 C9 179.83(16) . . . . ?
N1 C8 C9 C10 179.22(17) . . . . ?
N2 C8 C9 C10 -0.2(2) . . . . ?
N1 C8 C9 C14 0.3(3) . . . . ?
N2 C8 C9 C14 -179.14(14) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C14 C9 C10 C11 178.64(16) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 N2 0.0(3) . . . . ?
C11 C12 N2 C13 179.93(17) . . . . ?
C11 C12 N2 C8 -0.5(3) . . . . ?
N1 C8 N2 C13 0.72(18) . . . . ?
C9 C8 N2 C13 -179.71(15) . . . . ?
N1 C8 N2 C12 -178.97(15) . . . . ?
C9 C8 N2 C12 0.6(2) . . . . ?
C12 N2 C13 C7 179.19(16) . . . . ?
C8 N2 C13 C7 -0.46(18) . . . . ?
N1 C7 C13 N2 0.07(19) . . . . ?
C6 C7 C13 N2 -179.00(16) . . . . ?
C10 C9 C14 C15 -41.3(3) . . . . ?
C8 C9 C14 C15 137.59(18) . . . . ?
C10 C9 C14 C19 138.62(19) . . . . ?
C8 C9 C14 C19 -42.5(2) . . . . ?
C19 C14 C15 C16 1.3(3) . . . . ?
C9 C14 C15 C16 -178.78(18) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C15 C16 C17 C20 176.52(18) . . . . ?
C16 C17 C18 C19 2.0(3) . . . . ?
C20 C17 C18 C19 -175.71(17) . . . . ?
C17 C18 C19 C14 -1.2(3) . . . . ?
C15 C14 C19 C18 -0.5(3) . . . . ?
C9 C14 C19 C18 179.63(17) . . . . ?
C18 C17 C20 O3 -3.0(3) . . . . ?
C16 C17 C20 O3 179.3(2) . . . . ?
C18 C17 C20 O2 175.96(17) . . . . ?
C16 C17 C20 O2 -1.7(3) . . . . ?
O3 C20 O2 C21 2.7(3) . . . . ?
C17 C20 O2 C21 -176.3(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
O1 H1 N1 0.98(3) 1.71(3) 2.599(2) 148(3) .
C13 H9 O3 0.93 2.59 3.448(3) 154.4 2_645

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_68Ph2
_database_code_depnum_ccdc_archive 'CCDC 1447752'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '6,8-Diphenyl HPIP'
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 N2 O'
_chemical_formula_sum            'C25 H18 N2 O'
_chemical_formula_weight         362.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   10.436(1)
_cell_length_b                   14.221(1)
_cell_length_c                   12.880(1)
_cell_angle_alpha                90
_cell_angle_beta                 103.362(2)
_cell_angle_gamma                90
_cell_volume                     1859.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    18110
_cell_measurement_theta_min      4.35
_cell_measurement_theta_max      73.17

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8760
_exptl_absorpt_correction_T_max  0.9136
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5652
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.354
_diffrn_reflns_theta_max         73.167
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3475
_reflns_number_gt                3139
_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       'MacScience Xpress'
_computing_cell_refinement       Scalepack
_computing_data_reduction        'Denzo and Scalepack'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    maXus
_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)+(0.0295P)²+2.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1794
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_restrained_S_all      1.299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7873(3) 0.0868(3) 0.6614(2) 0.0804(9) Uani 1 1 d . . . . .
H1 H 0.742(5) 0.098(4) 0.578(4) 0.121 Uiso 1 1 d . U . . .
C1 C 0.6971(4) 0.0993(3) 0.7215(3) 0.0567(9) Uani 1 1 d . . . . .
C2 C 0.7382(4) 0.0939(3) 0.8316(3) 0.0715(12) Uani 1 1 d . . . . .
H2 H 0.8261 0.0809 0.8626 0.086 Uiso 1 1 calc R U . . .
C3 C 0.6518(5) 0.1074(3) 0.8954(3) 0.0751(13) Uani 1 1 d . . . . .
H3 H 0.6817 0.1050 0.9692 0.090 Uiso 1 1 calc R U . . .
C4 C 0.5208(5) 0.1244(3) 0.8510(3) 0.0683(11) Uani 1 1 d . . . . .
H4 H 0.4617 0.1329 0.8943 0.082 Uiso 1 1 calc R U . . .
C5 C 0.4784(4) 0.1286(3) 0.7422(3) 0.0562(9) Uani 1 1 d . . . . .
H5 H 0.3897 0.1393 0.7123 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5646(3) 0.1172(2) 0.6748(3) 0.0472(8) Uani 1 1 d . . . . .
C7 C 0.5165(3) 0.1245(2) 0.5589(2) 0.0444(7) Uani 1 1 d . . . . .
N1 N 0.6007(3) 0.11274(19) 0.4914(2) 0.0466(7) Uani 1 1 d . . . . .
C8 C 0.5268(3) 0.1234(2) 0.3926(3) 0.0456(8) Uani 1 1 d . . . . .
C9 C 0.5607(3) 0.1197(2) 0.2919(3) 0.0447(8) Uani 1 1 d . . . . .
C10 C 0.4611(3) 0.1347(2) 0.2045(3) 0.0481(8) Uani 1 1 d . . . . .
H6 H 0.4804 0.1311 0.1376 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3296(3) 0.1555(2) 0.2091(3) 0.0448(8) Uani 1 1 d . . . . .
C12 C 0.3001(3) 0.1583(2) 0.3064(3) 0.0476(8) Uani 1 1 d . . . . .
H7 H 0.2147 0.1712 0.3123 0.057 Uiso 1 1 calc R U . . .
N2 N 0.3976(3) 0.14187(19) 0.3956(2) 0.0435(6) Uani 1 1 d . . . . .
C13 C 0.3918(3) 0.1430(2) 0.5012(2) 0.0462(8) Uani 1 1 d . . . . .
H8 H 0.3177 0.1542 0.5281 0.055 Uiso 1 1 calc R U . . .
C14 C 0.6976(3) 0.1009(2) 0.2829(3) 0.0472(8) Uani 1 1 d . . . . .
C15 C 0.7438(4) 0.1422(3) 0.2012(3) 0.0551(9) Uani 1 1 d . . . . .
H9 H 0.6906 0.1845 0.1555 0.066 Uiso 1 1 calc R U . . .
C16 C 0.8680(4) 0.1212(3) 0.1867(3) 0.0674(11) Uani 1 1 d . . . . .
H10 H 0.8971 0.1489 0.1309 0.081 Uiso 1 1 calc R U . . .
C17 C 0.9485(4) 0.0600(3) 0.2541(3) 0.0661(11) Uani 1 1 d . . . . .
H11 H 1.0317 0.0459 0.2440 0.079 Uiso 1 1 calc R U . . .
C18 C 0.9050(4) 0.0197(3) 0.3366(3) 0.0628(10) Uani 1 1 d . . . . .
H12 H 0.9593 -0.0216 0.3828 0.075 Uiso 1 1 calc R U . . .
C19 C 0.7806(4) 0.0403(3) 0.3515(3) 0.0551(9) Uani 1 1 d . . . . .
H13 H 0.7526 0.0132 0.4081 0.066 Uiso 1 1 calc R U . . .
C20 C 0.2268(3) 0.1771(3) 0.1109(3) 0.0504(8) Uani 1 1 d . . . . .
C21 C 0.1334(3) 0.2462(3) 0.1116(3) 0.0595(10) Uani 1 1 d . . . . .
H14 H 0.1334 0.2779 0.1747 0.071 Uiso 1 1 calc R U . . .
C22 C 0.0402(4) 0.2687(3) 0.0198(4) 0.0759(13) Uani 1 1 d . . . . .
H15 H -0.0218 0.3153 0.0216 0.091 Uiso 1 1 calc R U . . .
C23 C 0.0391(5) 0.2229(4) -0.0730(4) 0.0850(16) Uani 1 1 d . . . . .
H16 H -0.0231 0.2386 -0.1347 0.102 Uiso 1 1 calc R U . . .
C24 C 0.1297(5) 0.1534(4) -0.0757(3) 0.0849(15) Uani 1 1 d . . . . .
H17 H 0.1277 0.1217 -0.1393 0.102 Uiso 1 1 calc R U . . .
C25 C 0.2251(4) 0.1299(3) 0.0163(3) 0.0671(11) Uani 1 1 d . . . . .
H18 H 0.2867 0.0831 0.0140 0.080 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.361(5) . ?
O1 H1 1.08(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.398(5) . ?
C2 C3 1.367(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.464(4) . ?
C7 C13 1.366(4) . ?
C7 N1 1.382(4) . ?
N1 C8 1.336(4) . ?
C8 N2 1.384(4) . ?
C8 C9 1.422(4) . ?
C9 C10 1.361(4) . ?
C9 C14 1.485(5) . ?
C10 C11 1.418(5) . ?
C10 H6 0.9300 . ?
C11 C12 1.359(4) . ?
C11 C20 1.489(4) . ?
C12 N2 1.366(4) . ?
C12 H7 0.9300 . ?
N2 C13 1.376(4) . ?
C13 H8 0.9300 . ?
C14 C15 1.385(5) . ?
C14 C19 1.385(5) . ?
C15 C16 1.385(5) . ?
C15 H9 0.9300 . ?
C16 C17 1.371(6) . ?
C16 H10 0.9300 . ?
C17 C18 1.373(6) . ?
C17 H11 0.9300 . ?
C18 C19 1.386(5) . ?
C18 H12 0.9300 . ?
C19 H13 0.9300 . ?
C20 C21 1.385(5) . ?
C20 C25 1.388(5) . ?
C21 C22 1.384(5) . ?
C21 H14 0.9300 . ?
C22 C23 1.359(7) . ?
C22 H15 0.9300 . ?
C23 C24 1.374(7) . ?
C23 H16 0.9300 . ?
C24 C25 1.401(6) . ?
C24 H17 0.9300 . ?
C25 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 110(3) . . ?
O1 C1 C2 118.9(4) . . ?
O1 C1 C6 121.6(3) . . ?
C2 C1 C6 119.5(4) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.9(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 120.5(3) . . ?
C1 C6 C7 121.6(3) . . ?
C13 C7 N1 110.2(3) . . ?
C13 C7 C6 128.8(3) . . ?
N1 C7 C6 121.0(3) . . ?
C8 N1 C7 106.0(3) . . ?
N1 C8 N2 110.3(3) . . ?
N1 C8 C9 130.9(3) . . ?
N2 C8 C9 118.8(3) . . ?
C10 C9 C8 116.4(3) . . ?
C10 C9 C14 122.0(3) . . ?
C8 C9 C14 121.6(3) . . ?
C9 C10 C11 124.0(3) . . ?
C9 C10 H6 118.0 . . ?
C11 C10 H6 118.0 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 C20 120.3(3) . . ?
C10 C11 C20 121.5(3) . . ?
C11 C12 N2 119.1(3) . . ?
C11 C12 H7 120.4 . . ?
N2 C12 H7 120.4 . . ?
C12 N2 C13 129.4(3) . . ?
C12 N2 C8 123.4(3) . . ?
C13 N2 C8 107.2(3) . . ?
C7 C13 N2 106.3(3) . . ?
C7 C13 H8 126.8 . . ?
N2 C13 H8 126.8 . . ?
C15 C14 C19 118.2(3) . . ?
C15 C14 C9 119.5(3) . . ?
C19 C14 C9 122.3(3) . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H9 119.6 . . ?
C14 C15 H9 119.6 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H10 119.8 . . ?
C15 C16 H10 119.8 . . ?
C16 C17 C18 119.4(4) . . ?
C16 C17 H11 120.3 . . ?
C18 C17 H11 120.3 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H12 119.8 . . ?
C19 C18 H12 119.8 . . ?
C14 C19 C18 120.7(4) . . ?
C14 C19 H13 119.7 . . ?
C18 C19 H13 119.7 . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C11 120.8(3) . . ?
C25 C20 C11 120.4(3) . . ?
C22 C21 C20 121.0(4) . . ?
C22 C21 H14 119.5 . . ?
C20 C21 H14 119.5 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H15 119.9 . . ?
C21 C22 H15 119.9 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H16 119.9 . . ?
C24 C23 H16 119.9 . . ?
C23 C24 C25 120.6(5) . . ?
C23 C24 H17 119.7 . . ?
C25 C24 H17 119.7 . . ?
C20 C25 C24 119.3(4) . . ?
C20 C25 H18 120.3 . . ?
C24 C25 H18 120.3 . . ?

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 C2 C3 179.0(4) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
C1 C2 C3 C4 1.6(7) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
O1 C1 C6 C5 179.6(4) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
O1 C1 C6 C7 -0.8(6) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
C5 C6 C7 C13 0.7(5) . . . . ?
C1 C6 C7 C13 -178.8(4) . . . . ?
C5 C6 C7 N1 -179.6(3) . . . . ?
C1 C6 C7 N1 0.9(5) . . . . ?
C13 C7 N1 C8 -0.4(4) . . . . ?
C6 C7 N1 C8 179.8(3) . . . . ?
C7 N1 C8 N2 0.1(4) . . . . ?
C7 N1 C8 C9 179.4(3) . . . . ?
N1 C8 C9 C10 -179.4(3) . . . . ?
N2 C8 C9 C10 -0.1(5) . . . . ?
N1 C8 C9 C14 0.3(6) . . . . ?
N2 C8 C9 C14 179.6(3) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C14 C9 C10 C11 -178.2(3) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C9 C10 C11 C20 176.1(3) . . . . ?
C10 C11 C12 N2 0.5(5) . . . . ?
C20 C11 C12 N2 -177.4(3) . . . . ?
C11 C12 N2 C13 178.4(3) . . . . ?
C11 C12 N2 C8 0.8(5) . . . . ?
N1 C8 N2 C12 178.3(3) . . . . ?
C9 C8 N2 C12 -1.1(5) . . . . ?
N1 C8 N2 C13 0.3(4) . . . . ?
C9 C8 N2 C13 -179.1(3) . . . . ?
N1 C7 C13 N2 0.6(4) . . . . ?
C6 C7 C13 N2 -179.7(3) . . . . ?
C12 N2 C13 C7 -178.4(3) . . . . ?
C8 N2 C13 C7 -0.5(4) . . . . ?
C10 C9 C14 C15 32.5(5) . . . . ?
C8 C9 C14 C15 -147.1(3) . . . . ?
C10 C9 C14 C19 -145.0(4) . . . . ?
C8 C9 C14 C19 35.3(5) . . . . ?
C19 C14 C15 C16 1.9(5) . . . . ?
C9 C14 C15 C16 -175.8(3) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C15 C14 C19 C18 -1.8(5) . . . . ?
C9 C14 C19 C18 175.8(3) . . . . ?
C17 C18 C19 C14 0.7(6) . . . . ?
C12 C11 C20 C21 36.8(5) . . . . ?
C10 C11 C20 C21 -141.0(3) . . . . ?
C12 C11 C20 C25 -144.9(4) . . . . ?
C10 C11 C20 C25 37.3(5) . . . . ?
C25 C20 C21 C22 -0.4(5) . . . . ?
C11 C20 C21 C22 177.9(3) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C24 0.7(7) . . . . ?
C22 C23 C24 C25 -0.9(7) . . . . ?
C21 C20 C25 C24 0.2(6) . . . . ?
C11 C20 C25 C24 -178.1(3) . . . . ?
C23 C24 C25 C20 0.5(6) . . . . ?

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
O1 H1 N1 1.08(5) 1.64(5) 2.599(4) 145(4) .

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



