# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_zhaoyl20210514_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2161364'
loop_
_audit_author_name
_audit_author_address
'Han '
;,
China
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H30 Br2 N4'
_chemical_formula_weight         774.54

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   11.5554(7)
_cell_length_b                   9.8030(5)
_cell_length_c                   30.5065(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.730(3)
_cell_angle_gamma                90
_cell_volume                     3431.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      63.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    3.295
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35514
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         63.768
_diffrn_reflns_theta_full        63.768
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5660
_reflns_number_gt                4985
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+2.0527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5660
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61001(2) 0.63966(3) 0.15822(2) 0.04972(10) Uani 1 1 d . . . . .
Br2 Br 0.58959(3) -0.11876(3) 0.07136(2) 0.06948(12) Uani 1 1 d . . . . .
C1 C 0.4260(2) -0.2239(2) 0.24030(7) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.4272(2) -0.3395(3) 0.26652(8) 0.0473(6) Uani 1 1 d . . . . .
H2 H 0.4822 -0.3480 0.2912 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3466(3) -0.4421(3) 0.25603(9) 0.0533(7) Uani 1 1 d . . . . .
H3 H 0.3487 -0.5204 0.2733 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2632(2) -0.4291(3) 0.22005(9) 0.0504(6) Uani 1 1 d . . . . .
H4 H 0.2072 -0.4967 0.2136 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2635(2) -0.3144(3) 0.19360(8) 0.0423(6) Uani 1 1 d . . . . .
H5 H 0.2078 -0.3062 0.1691 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3451(2) -0.2113(2) 0.20275(7) 0.0358(5) Uani 1 1 d . . . . .
C7 C 0.3522(2) -0.0933(2) 0.17174(8) 0.0432(6) Uani 1 1 d . . . . .
H7A H 0.2739 -0.0618 0.1619 0.052 Uiso 1 1 calc R U . . .
H7B H 0.3863 -0.1249 0.1460 0.052 Uiso 1 1 calc R U . . .
C8 C 0.42280(19) 0.0253(2) 0.19159(7) 0.0326(5) Uani 1 1 d . . . . .
C9 C 0.50130(19) 0.0052(2) 0.23130(7) 0.0343(5) Uani 1 1 d . . . . .
C10 C 0.57061(19) 0.2250(2) 0.23039(7) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.49624(19) 0.2564(2) 0.19141(7) 0.0324(5) Uani 1 1 d . . . . .
C12 C 0.41769(19) 0.1527(2) 0.17324(7) 0.0327(5) Uani 1 1 d . . . . .
C13 C 0.32977(19) 0.1883(2) 0.13481(7) 0.0343(5) Uani 1 1 d . . . . .
C14 C 0.2331(2) 0.2607(3) 0.14216(9) 0.0505(6) Uani 1 1 d . . . . .
H14 H 0.2218 0.2847 0.1708 0.061 Uiso 1 1 calc R U . . .
C15 C 0.1514(3) 0.2989(3) 0.10729(11) 0.0639(8) Uani 1 1 d . . . . .
H15 H 0.0860 0.3485 0.1128 0.077 Uiso 1 1 calc R U . . .
C16 C 0.1663(3) 0.2645(3) 0.06550(10) 0.0644(9) Uani 1 1 d . . . . .
H16 H 0.1119 0.2914 0.0422 0.077 Uiso 1 1 calc R U . . .
C17 C 0.2610(3) 0.1906(4) 0.05759(10) 0.0811(11) Uani 1 1 d . . . . .
H17 H 0.2707 0.1653 0.0289 0.097 Uiso 1 1 calc R U . . .
C18 C 0.3438(3) 0.1525(4) 0.09228(9) 0.0656(9) Uani 1 1 d . . . . .
H18 H 0.4088 0.1025 0.0866 0.079 Uiso 1 1 calc R U . . .
C19 C 0.5073(2) 0.3836(2) 0.17109(7) 0.0361(5) Uani 1 1 d . . . . .
H19 H 0.4584 0.4062 0.1457 0.043 Uiso 1 1 calc R U . . .
C20 C 0.5898(2) 0.4739(2) 0.18870(7) 0.0367(5) Uani 1 1 d . . . . .
C21 C 0.6623(2) 0.4457(2) 0.22765(8) 0.0400(5) Uani 1 1 d . . . . .
H21 H 0.7171 0.5093 0.2394 0.048 Uiso 1 1 calc R U . . .
C22 C 0.6514(2) 0.3236(2) 0.24809(7) 0.0385(5) Uani 1 1 d . . . . .
H22 H 0.6984 0.3050 0.2743 0.046 Uiso 1 1 calc R U . . .
C23 C 0.7935(2) 0.2614(3) 0.13328(7) 0.0378(5) Uani 1 1 d . . . . .
C24 C 0.7690(2) 0.1490(3) 0.15957(8) 0.0461(6) Uani 1 1 d . . . . .
H24 H 0.7937 0.1505 0.1897 0.055 Uiso 1 1 calc R U . . .
C25 C 0.7098(2) 0.0382(3) 0.14169(9) 0.0497(6) Uani 1 1 d . . . . .
H25 H 0.6941 -0.0350 0.1595 0.060 Uiso 1 1 calc R U . . .
C26 C 0.6726(2) 0.0355(3) 0.09628(9) 0.0473(6) Uani 1 1 d . . . . .
C27 C 0.6939(2) 0.1412(2) 0.06954(8) 0.0440(6) Uani 1 1 d . . . . .
H27 H 0.6679 0.1375 0.0395 0.053 Uiso 1 1 calc R U . . .
C28 C 0.7551(2) 0.2563(2) 0.08727(7) 0.0370(5) Uani 1 1 d . . . . .
C29 C 0.7818(2) 0.3700(2) 0.06106(7) 0.0367(5) Uani 1 1 d . . . . .
C30 C 0.8398(2) 0.4791(3) 0.08070(7) 0.0413(6) Uani 1 1 d . . . . .
C31 C 0.8705(2) 0.4751(3) 0.12778(7) 0.0399(5) Uani 1 1 d . . . . .
C32 C 0.9418(2) 0.7095(2) 0.12702(8) 0.0397(5) Uani 1 1 d . . . . .
C33 C 0.9165(2) 0.7205(3) 0.08140(8) 0.0433(6) Uani 1 1 d . . . . .
C34 C 0.8756(4) 0.5980(3) 0.05454(9) 0.0764(11) Uani 1 1 d . . . . .
H34A H 0.9376 0.5689 0.0378 0.092 Uiso 1 1 calc R U . . .
H34B H 0.8099 0.6247 0.0335 0.092 Uiso 1 1 calc R U . . .
C35 C 0.9325(2) 0.8443(3) 0.06143(9) 0.0499(6) Uani 1 1 d . . . . .
H35 H 0.9128 0.8529 0.0311 0.060 Uiso 1 1 calc R U . . .
C36 C 0.9771(2) 0.9557(3) 0.08529(9) 0.0538(7) Uani 1 1 d . . . . .
H36 H 0.9887 1.0379 0.0713 0.065 Uiso 1 1 calc R U . . .
C37 C 1.0043(2) 0.9430(3) 0.13025(9) 0.0546(7) Uani 1 1 d . . . . .
H37 H 1.0353 1.0171 0.1466 0.066 Uiso 1 1 calc R U . . .
C38 C 0.9860(2) 0.8224(3) 0.15115(8) 0.0471(6) Uani 1 1 d . . . . .
H38 H 1.0031 0.8160 0.1816 0.057 Uiso 1 1 calc R U . . .
C39 C 0.7458(2) 0.3684(2) 0.01226(7) 0.0360(5) Uani 1 1 d . . . . .
C40 C 0.6498(3) 0.4399(4) -0.00587(9) 0.0661(9) Uani 1 1 d . . . . .
H40 H 0.6070 0.4907 0.0123 0.079 Uiso 1 1 calc R U . . .
C41 C 0.6159(3) 0.4375(4) -0.05109(9) 0.0726(10) Uani 1 1 d . . . . .
H41 H 0.5500 0.4857 -0.0627 0.087 Uiso 1 1 calc R U . . .
C42 C 0.6770(3) 0.3662(3) -0.07829(8) 0.0548(7) Uani 1 1 d . . . . .
H42 H 0.6539 0.3652 -0.1085 0.066 Uiso 1 1 calc R U . . .
C43 C 0.7732(3) 0.2955(4) -0.06097(9) 0.0703(9) Uani 1 1 d . . . . .
H43 H 0.8163 0.2464 -0.0795 0.084 Uiso 1 1 calc R U . . .
C44 C 0.8071(3) 0.2968(3) -0.01581(9) 0.0600(8) Uani 1 1 d . . . . .
H44 H 0.8727 0.2478 -0.0044 0.072 Uiso 1 1 calc R U . . .
N1 N 0.50675(19) -0.1197(2) 0.25127(7) 0.0418(5) Uani 1 1 d . . . . .
N2 N 0.56894(16) 0.10089(19) 0.25075(6) 0.0357(4) Uani 1 1 d . . . . .
N3 N 0.85168(17) 0.3709(2) 0.15288(6) 0.0394(5) Uani 1 1 d . . . . .
N4 N 0.9262(2) 0.5862(2) 0.14820(7) 0.0474(5) Uani 1 1 d . . . . .
H4A H 0.925(2) 0.590(3) 0.1748(10) 0.047(8) Uiso 1 1 d . . . . .
H1A H 0.552(2) -0.128(3) 0.2726(10) 0.048(8) Uiso 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
Br1 C20 1.900(2) . ?
Br2 C26 1.901(3) . ?
C1 C2 1.386(3) . ?
C1 N1 1.397(3) . ?
C1 C6 1.397(3) . ?
C2 C3 1.382(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.388(3) . ?
C6 C7 1.503(3) . ?
C7 C8 1.506(3) . ?
C8 C12 1.367(3) . ?
C8 C9 1.439(3) . ?
C9 N2 1.317(3) . ?
C9 N1 1.365(3) . ?
C10 N2 1.368(3) . ?
C10 C22 1.407(3) . ?
C10 C11 1.417(3) . ?
C11 C19 1.405(3) . ?
C11 C12 1.431(3) . ?
C12 C13 1.500(3) . ?
C13 C14 1.364(4) . ?
C13 C18 1.372(4) . ?
C14 C15 1.389(4) . ?
C15 C16 1.349(5) . ?
C16 C17 1.358(5) . ?
C17 C18 1.392(4) . ?
C19 C20 1.364(3) . ?
C20 C21 1.399(3) . ?
C21 C22 1.362(3) . ?
C23 N3 1.367(3) . ?
C23 C24 1.411(3) . ?
C23 C28 1.422(3) . ?
C24 C25 1.363(4) . ?
C25 C26 1.402(4) . ?
C26 C27 1.359(3) . ?
C27 C28 1.406(3) . ?
C28 C29 1.426(3) . ?
C29 C30 1.364(3) . ?
C29 C39 1.498(3) . ?
C30 C31 1.439(3) . ?
C30 C34 1.498(4) . ?
C31 N3 1.311(3) . ?
C31 N4 1.376(3) . ?
C32 N4 1.392(3) . ?
C32 C33 1.393(3) . ?
C32 C38 1.393(3) . ?
C33 C35 1.381(4) . ?
C33 C34 1.498(4) . ?
C35 C36 1.378(4) . ?
C36 C37 1.376(4) . ?
C37 C38 1.371(4) . ?
C39 C44 1.367(4) . ?
C39 C40 1.373(4) . ?
C40 C41 1.390(4) . ?
C41 C42 1.347(4) . ?
C42 C43 1.362(4) . ?
C43 C44 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.9(2) . . ?
C2 C1 C6 120.3(2) . . ?
N1 C1 C6 119.8(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 119.3(2) . . ?
C4 C5 C6 121.5(2) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 121.4(2) . . ?
C1 C6 C7 120.2(2) . . ?
C6 C7 C8 114.11(18) . . ?
C12 C8 C9 117.6(2) . . ?
C12 C8 C7 123.03(19) . . ?
C9 C8 C7 119.38(19) . . ?
N2 C9 N1 116.36(19) . . ?
N2 C9 C8 124.3(2) . . ?
N1 C9 C8 119.4(2) . . ?
N2 C10 C22 118.74(19) . . ?
N2 C10 C11 122.3(2) . . ?
C22 C10 C11 118.9(2) . . ?
C19 C11 C10 119.1(2) . . ?
C19 C11 C12 123.10(19) . . ?
C10 C11 C12 117.7(2) . . ?
C8 C12 C11 119.71(19) . . ?
C8 C12 C13 121.73(19) . . ?
C11 C12 C13 118.55(19) . . ?
C14 C13 C18 118.6(2) . . ?
C14 C13 C12 119.1(2) . . ?
C18 C13 C12 122.4(2) . . ?
C13 C14 C15 120.7(3) . . ?
C16 C15 C14 120.4(3) . . ?
C15 C16 C17 119.8(3) . . ?
C16 C17 C18 120.3(3) . . ?
C13 C18 C17 120.2(3) . . ?
C20 C19 C11 119.8(2) . . ?
C19 C20 C21 121.9(2) . . ?
C19 C20 Br1 118.84(17) . . ?
C21 C20 Br1 119.24(17) . . ?
C22 C21 C20 118.9(2) . . ?
C21 C22 C10 121.4(2) . . ?
N3 C23 C24 119.1(2) . . ?
N3 C23 C28 122.7(2) . . ?
C24 C23 C28 118.3(2) . . ?
C25 C24 C23 121.3(2) . . ?
C24 C25 C26 119.5(2) . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 Br2 119.0(2) . . ?
C25 C26 Br2 119.49(19) . . ?
C26 C27 C28 120.0(2) . . ?
C27 C28 C23 119.5(2) . . ?
C27 C28 C29 122.9(2) . . ?
C23 C28 C29 117.6(2) . . ?
C30 C29 C28 119.6(2) . . ?
C30 C29 C39 120.6(2) . . ?
C28 C29 C39 119.7(2) . . ?
C29 C30 C31 117.9(2) . . ?
C29 C30 C34 121.9(2) . . ?
C31 C30 C34 120.1(2) . . ?
N3 C31 N4 117.0(2) . . ?
N3 C31 C30 124.5(2) . . ?
N4 C31 C30 118.5(2) . . ?
N4 C32 C33 120.5(2) . . ?
N4 C32 C38 120.3(2) . . ?
C33 C32 C38 119.2(2) . . ?
C35 C33 C32 119.0(2) . . ?
C35 C33 C34 120.9(2) . . ?
C32 C33 C34 120.1(2) . . ?
C33 C34 C30 114.9(2) . . ?
C36 C35 C33 121.7(2) . . ?
C37 C36 C35 118.8(3) . . ?
C38 C37 C36 120.8(2) . . ?
C37 C38 C32 120.4(2) . . ?
C44 C39 C40 117.6(2) . . ?
C44 C39 C29 121.6(2) . . ?
C40 C39 C29 120.8(2) . . ?
C39 C40 C41 120.8(3) . . ?
C42 C41 C40 120.9(3) . . ?
C41 C42 C43 119.2(2) . . ?
C42 C43 C44 120.2(3) . . ?
C39 C44 C43 121.3(3) . . ?
C9 N1 C1 123.64(19) . . ?
C9 N2 C10 117.95(18) . . ?
C31 N3 C23 117.64(19) . . ?
C31 N4 C32 123.8(2) . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_31
_database_code_depnum_ccdc_archive 'CCDC 1994944'
loop_
_audit_author_name
_audit_author_address
'Han '
;,
China
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2022-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2 O2'
_chemical_formula_weight         378.41

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'
N N 0.0311 0.0180 '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'

_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                   16.4410(7)
_cell_length_b                   9.0188(4)
_cell_length_c                   13.5111(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.503(2)
_cell_angle_gamma                90
_cell_volume                     1955.89(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7725
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      71.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.657
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14261
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         72.252
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3802
_reflns_number_gt                2953
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.5688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3802
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
H1A H 0.6114(14) 1.044(2) 0.7281(16) 0.064(6) Uiso 1 1 d . . . . .
C1 C 0.70184(10) 1.01343(18) 0.85238(12) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.76652(9) 1.11208(18) 0.90166(12) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.82069(9) 1.06338(17) 0.98793(11) 0.0376(3) Uani 1 1 d . . . . .
C4 C 0.80775(9) 0.91754(17) 1.02227(11) 0.0365(3) Uani 1 1 d . . . . .
C5 C 0.73863(9) 0.83258(17) 0.96908(11) 0.0379(3) Uani 1 1 d . . . . .
C6 C 0.72243(10) 0.69010(18) 1.00759(12) 0.0418(4) Uani 1 1 d . . . . .
C7 C 0.77614(11) 0.63652(19) 1.09269(14) 0.0506(4) Uani 1 1 d . . . . .
H7 H 0.7659 0.5440 1.1179 0.061 Uiso 1 1 calc R U . . .
C8 C 0.84565(11) 0.7175(2) 1.14222(13) 0.0499(4) Uani 1 1 d . . . . .
H8 H 0.8818 0.6773 1.1984 0.060 Uiso 1 1 calc R U . . .
C9 C 0.86046(10) 0.85498(18) 1.10844(12) 0.0435(4) Uani 1 1 d . . . . .
H9 H 0.9062 0.9086 1.1428 0.052 Uiso 1 1 calc R U . . .
C10 C 0.75516(10) 1.24932(18) 0.84437(12) 0.0417(4) Uani 1 1 d . . . . .
C11 C 0.68627(10) 1.2261(2) 0.76316(13) 0.0465(4) Uani 1 1 d . . . . .
C12 C 0.65758(12) 1.3368(2) 0.69311(15) 0.0569(5) Uani 1 1 d . . . . .
H12 H 0.6130 1.3207 0.6388 0.068 Uiso 1 1 calc R U . . .
C13 C 0.69782(12) 1.4717(2) 0.70728(16) 0.0594(5) Uani 1 1 d . . . . .
H13 H 0.6799 1.5476 0.6611 0.071 Uiso 1 1 calc R U . . .
C14 C 0.76419(12) 1.4981(2) 0.78813(15) 0.0543(5) Uani 1 1 d . . . . .
H14 H 0.7890 1.5913 0.7961 0.065 Uiso 1 1 calc R U . . .
C15 C 0.79361(11) 1.38746(19) 0.85647(14) 0.0469(4) Uani 1 1 d . . . . .
H15 H 0.8386 1.4048 0.9101 0.056 Uiso 1 1 calc R U . . .
C16 C 0.88683(10) 1.16370(17) 1.04465(11) 0.0382(4) Uani 1 1 d . . . . .
C17 C 0.87592(11) 1.2339(2) 1.13162(12) 0.0473(4) Uani 1 1 d . . . . .
H17 H 0.8297 1.2116 1.1581 0.057 Uiso 1 1 calc R U . . .
C18 C 0.93341(12) 1.3374(2) 1.17970(14) 0.0569(5) Uani 1 1 d . . . . .
H18 H 0.9255 1.3842 1.2382 0.068 Uiso 1 1 calc R U . . .
C19 C 1.00183(12) 1.3711(2) 1.14136(14) 0.0578(5) Uani 1 1 d . . . . .
H19 H 1.0398 1.4418 1.1731 0.069 Uiso 1 1 calc R U . . .
C20 C 1.01405(12) 1.3006(3) 1.05648(16) 0.0657(6) Uani 1 1 d . . . . .
H20 H 1.0608 1.3224 1.0309 0.079 Uiso 1 1 calc R U . . .
C21 C 0.95713(11) 1.1967(2) 1.00833(15) 0.0576(5) Uani 1 1 d . . . . .
H21 H 0.9662 1.1486 0.9508 0.069 Uiso 1 1 calc R U . . .
C22 C 0.64833(11) 0.60870(19) 0.95621(13) 0.0449(4) Uani 1 1 d . . . . .
H22 H 0.6103 0.6611 0.9078 0.054 Uiso 1 1 calc R U . . .
C23 C 0.62943(11) 0.47014(19) 0.97060(13) 0.0473(4) Uani 1 1 d . . . . .
H23 H 0.6655 0.4133 1.0183 0.057 Uiso 1 1 calc R U . . .
C24 C 0.55271(11) 0.4039(2) 0.91285(14) 0.0494(4) Uani 1 1 d . . . . .
C25 C 0.47810(16) 0.1798(3) 0.8758(2) 0.1021(10) Uani 1 1 d . . . . .
H25A H 0.4301 0.2106 0.9002 0.153 Uiso 1 1 calc R U . . .
H25B H 0.4865 0.0752 0.8866 0.153 Uiso 1 1 calc R U . . .
H25C H 0.4695 0.2010 0.8046 0.153 Uiso 1 1 calc R U . . .
N1 N 0.65620(10) 1.08300(17) 0.76817(11) 0.0505(4) Uani 1 1 d . . . . .
N2 N 0.68570(8) 0.88095(15) 0.88259(10) 0.0437(3) Uani 1 1 d . . . . .
O1 O 0.55040(9) 0.25868(16) 0.92961(12) 0.0739(4) Uani 1 1 d . . . . .
O2 O 0.49814(9) 0.46870(18) 0.85604(12) 0.0770(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.308(2) . ?
C1 N1 1.372(2) . ?
C1 C2 1.435(2) . ?
C2 C3 1.377(2) . ?
C2 C10 1.450(2) . ?
C3 C4 1.426(2) . ?
C3 C16 1.493(2) . ?
C4 C9 1.410(2) . ?
C4 C5 1.429(2) . ?
C5 N2 1.369(2) . ?
C5 C6 1.433(2) . ?
C6 C7 1.377(2) . ?
C6 C22 1.462(2) . ?
C7 C8 1.399(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.391(2) . ?
C10 C11 1.412(2) . ?
C11 C12 1.387(2) . ?
C11 N1 1.389(2) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 C21 1.382(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.312(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.460(2) . ?
C23 H23 0.9300 . ?
C24 O2 1.199(2) . ?
C24 O1 1.331(2) . ?
C25 O1 1.440(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1A 0.89(2) . ?

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
N2 C1 N1 124.41(15) . . ?
N2 C1 C2 126.98(15) . . ?
N1 C1 C2 108.58(15) . . ?
C3 C2 C1 118.27(14) . . ?
C3 C2 C10 135.16(15) . . ?
C1 C2 C10 106.54(14) . . ?
C2 C3 C4 117.07(14) . . ?
C2 C3 C16 120.48(14) . . ?
C4 C3 C16 122.38(14) . . ?
C9 C4 C3 121.97(14) . . ?
C9 C4 C5 118.72(14) . . ?
C3 C4 C5 119.31(14) . . ?
N2 C5 C4 123.23(14) . . ?
N2 C5 C6 117.53(14) . . ?
C4 C5 C6 119.24(14) . . ?
C7 C6 C5 118.81(15) . . ?
C7 C6 C22 122.55(15) . . ?
C5 C6 C22 118.62(14) . . ?
C6 C7 C8 121.75(16) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 120.15(16) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 121.25(15) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C15 C10 C11 119.49(16) . . ?
C15 C10 C2 134.36(16) . . ?
C11 C10 C2 106.08(14) . . ?
C12 C11 N1 129.09(17) . . ?
C12 C11 C10 121.38(17) . . ?
N1 C11 C10 109.53(14) . . ?
C13 C12 C11 117.32(18) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C14 122.20(17) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 120.46(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.12(17) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
C17 C16 C21 118.43(15) . . ?
C17 C16 C3 120.05(14) . . ?
C21 C16 C3 121.37(15) . . ?
C16 C17 C18 120.45(17) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.29(17) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.79(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.24(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.77(18) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C23 C22 C6 127.39(17) . . ?
C23 C22 H22 116.3 . . ?
C6 C22 H22 116.3 . . ?
C22 C23 C24 121.03(17) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
O2 C24 O1 122.93(17) . . ?
O2 C24 C23 125.66(18) . . ?
O1 C24 C23 111.40(16) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C11 109.20(14) . . ?
C1 N1 H1A 124.1(14) . . ?
C11 N1 H1A 126.4(13) . . ?
C1 N2 C5 115.03(13) . . ?
C24 O1 C25 116.80(19) . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.038

