# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_0877_tes
_database_code_depnum_ccdc_archive 'CCDC 2060600'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N3 O2'
_chemical_formula_sum            'C25 H23 N3 O2'
_chemical_formula_weight         397.46
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7539(3)
_cell_length_b                   10.3038(5)
_cell_length_c                   13.4620(6)
_cell_angle_alpha                107.202(2)
_cell_angle_beta                 98.294(2)
_cell_angle_gamma                96.619(2)
_cell_volume                     1002.39(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1276 before and 0.0508 after correction. 
The Ratio of minimum to maximum transmission is 0.8207.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32154
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.430
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4000
_reflns_number_total             5032
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.3483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.08520(13) 0.40035(10) 0.88542(8) 0.0290(2) Uani 1 1 d . . . . .
O2 O 0.35304(11) 0.45030(8) 0.84400(6) 0.01786(19) Uani 1 1 d . . . . .
N1 N 0.28853(13) 0.34085(10) 0.74262(8) 0.0155(2) Uani 1 1 d . . . . .
N2 N 0.35664(13) 0.28096(10) 0.46986(8) 0.0158(2) Uani 1 1 d . . . . .
H2 H 0.4128(19) 0.3526(15) 0.4581(11) 0.019 Uiso 1 1 d R . . . .
N3 N 0.34098(13) 0.58296(10) 0.59404(8) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.36397(19) 0.79955(15) 0.91857(12) 0.0303(3) Uani 1 1 d . . . . .
H1 H 0.481733 0.781454 0.922610 0.036 Uiso 1 1 calc R . . . .
C2 C 0.3165(2) 0.90207(15) 0.87779(13) 0.0352(4) Uani 1 1 d . . . . .
H2A H 0.401940 0.953989 0.854362 0.042 Uiso 1 1 calc R . . . .
C3 C 0.1459(2) 0.92869(14) 0.87122(12) 0.0310(3) Uani 1 1 d . . . . .
H3 H 0.113129 0.998230 0.842652 0.037 Uiso 1 1 calc R . . . .
C4 C 0.02256(19) 0.85381(14) 0.90635(11) 0.0267(3) Uani 1 1 d . . . . .
H4 H -0.094894 0.872587 0.902531 0.032 Uiso 1 1 calc R . . . .
C5 C 0.06946(18) 0.75158(13) 0.94708(10) 0.0231(3) Uani 1 1 d . . . . .
H5 H -0.016208 0.700357 0.970836 0.028 Uiso 1 1 calc R . . . .
C6 C 0.24084(17) 0.72328(13) 0.95349(10) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.28674(18) 0.60638(13) 0.99373(10) 0.0236(3) Uani 1 1 d . . . . .
H7A H 0.415976 0.619079 1.018521 0.028 Uiso 1 1 calc R . . . .
H7B H 0.227276 0.604735 1.053774 0.028 Uiso 1 1 calc R . . . .
C8 C 0.22556(17) 0.47320(13) 0.90384(10) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.34643(17) 0.21401(12) 0.75503(10) 0.0185(3) Uani 1 1 d . . . . .
H9A H 0.309128 0.196508 0.817845 0.022 Uiso 1 1 calc R . . . .
H9B H 0.476876 0.224167 0.765072 0.022 Uiso 1 1 calc R . . . .
C10 C 0.26233(17) 0.09402(12) 0.65519(10) 0.0193(3) Uani 1 1 d . . . . .
H10A H 0.319414 0.012569 0.653980 0.023 Uiso 1 1 calc R . . . .
H10B H 0.134946 0.068988 0.654611 0.023 Uiso 1 1 calc R . . . .
C11 C 0.28557(15) 0.13640(12) 0.56033(10) 0.0160(2) Uani 1 1 d . . . . .
C12 C 0.26754(15) 0.05686(12) 0.45100(10) 0.0171(2) Uani 1 1 d . . . . .
C13 C 0.21063(16) -0.08268(12) 0.39167(10) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.175197 -0.147772 0.425260 0.025 Uiso 1 1 calc R . . . .
C14 C 0.20683(17) -0.12401(13) 0.28401(11) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.165698 -0.217894 0.243340 0.028 Uiso 1 1 calc R . . . .
C15 C 0.26253(17) -0.03006(13) 0.23356(10) 0.0236(3) Uani 1 1 d . . . . .
H15 H 0.261690 -0.061840 0.159637 0.028 Uiso 1 1 calc R . . . .
C16 C 0.31884(17) 0.10841(13) 0.28956(10) 0.0205(3) Uani 1 1 d . . . . .
H16 H 0.357249 0.172229 0.255575 0.025 Uiso 1 1 calc R . . . .
C17 C 0.31689(15) 0.15025(12) 0.39743(9) 0.0162(2) Uani 1 1 d . . . . .
C18 C 0.33837(15) 0.27010(12) 0.56762(9) 0.0145(2) Uani 1 1 d . . . . .
C19 C 0.36975(15) 0.39379(11) 0.66592(9) 0.0143(2) Uani 1 1 d . . . . .
C20 C 0.56884(16) 0.45271(12) 0.70174(10) 0.0186(3) Uani 1 1 d . . . . .
H20A H 0.586027 0.538395 0.761081 0.028 Uiso 1 1 calc GR . . . .
H20B H 0.615863 0.471527 0.642713 0.028 Uiso 1 1 calc GR . . . .
H20C H 0.631101 0.385627 0.724183 0.028 Uiso 1 1 calc GR . . . .
C21 C 0.26477(15) 0.50271(11) 0.64337(9) 0.0137(2) Uani 1 1 d . . . . .
C22 C 0.09846(16) 0.51412(12) 0.66934(9) 0.0166(2) Uani 1 1 d . . . . .
H22 H 0.046171 0.454273 0.702561 0.020 Uiso 1 1 calc R . . . .
C23 C 0.01065(16) 0.61405(12) 0.64596(10) 0.0182(3) Uani 1 1 d . . . . .
H23 H -0.101797 0.624957 0.664343 0.022 Uiso 1 1 calc R . . . .
C24 C 0.08806(16) 0.69774(12) 0.59566(10) 0.0188(3) Uani 1 1 d . . . . .
H24 H 0.030441 0.766964 0.578535 0.023 Uiso 1 1 calc R . . . .
C25 C 0.25173(17) 0.67772(12) 0.57102(10) 0.0193(3) Uani 1 1 d . . . . .
H25 H 0.304443 0.734482 0.535598 0.023 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.1971(16) . ?
O2 N1 1.4654(12) . ?
O2 C8 1.3613(15) . ?
N1 C9 1.4766(15) . ?
N1 C19 1.4838(15) . ?
N2 H2 0.880(15) . ?
N2 C17 1.3785(15) . ?
N2 C18 1.3792(15) . ?
N3 C21 1.3414(15) . ?
N3 C25 1.3420(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.3874(19) . ?
C2 H2A 0.9500 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3837(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3891(19) . ?
C6 C7 1.5166(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5081(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5293(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.4939(17) . ?
C11 C12 1.4347(17) . ?
C11 C18 1.3614(16) . ?
C12 C13 1.4046(17) . ?
C12 C17 1.4135(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3793(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.401(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3855(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3901(17) . ?
C18 C19 1.5076(16) . ?
C19 C20 1.5428(16) . ?
C19 C21 1.5347(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.3927(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3835(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3805(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.3801(17) . ?
C25 H25 0.9500 . ?

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
C8 O2 N1 112.35(9) . . ?
O2 N1 C9 107.01(8) . . ?
O2 N1 C19 103.77(8) . . ?
C9 N1 C19 114.55(9) . . ?
C17 N2 H2 123.8(9) . . ?
C17 N2 C18 107.90(10) . . ?
C18 N2 H2 126.0(9) . . ?
C21 N3 C25 117.50(10) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.57(14) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.14(14) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.72(14) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.27(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.51(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.79(12) . . ?
C1 C6 C7 121.68(12) . . ?
C5 C6 C7 119.48(12) . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 C6 108.00(10) . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
O1 C8 O2 124.81(11) . . ?
O1 C8 C7 125.84(12) . . ?
O2 C8 C7 109.32(11) . . ?
N1 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
N1 C9 C10 108.29(10) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 108.87(10) . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C12 C11 C10 131.26(11) . . ?
C18 C11 C10 122.12(11) . . ?
C18 C11 C12 106.59(11) . . ?
C13 C12 C11 134.87(12) . . ?
C13 C12 C17 118.43(11) . . ?
C17 C12 C11 106.67(10) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.16(12) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.19(12) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.17(12) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.37(12) . . ?
C17 C16 H16 121.3 . . ?
N2 C17 C12 108.10(10) . . ?
N2 C17 C16 129.30(11) . . ?
C16 C17 C12 122.60(11) . . ?
N2 C18 C19 122.50(10) . . ?
C11 C18 N2 110.71(10) . . ?
C11 C18 C19 126.78(11) . . ?
N1 C19 C18 103.81(9) . . ?
N1 C19 C20 114.74(10) . . ?
N1 C19 C21 107.39(9) . . ?
C18 C19 C20 110.45(9) . . ?
C18 C19 C21 109.18(9) . . ?
C21 C19 C20 110.93(9) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C19 115.69(10) . . ?
N3 C21 C22 122.28(11) . . ?
C22 C21 C19 121.99(10) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.91(11) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.34(11) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 121.0 . . ?
C25 C24 C23 117.94(11) . . ?
C25 C24 H24 121.0 . . ?
N3 C25 C24 124.00(11) . . ?
N3 C25 H25 118.0 . . ?
C24 C25 H25 118.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0732_lc
_database_code_depnum_ccdc_archive 'CCDC 2060601'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 N2 O2'
_chemical_formula_sum            'C25 H22 N2 O2'
_chemical_formula_weight         382.44
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.5752(5)
_cell_length_b                   12.0481(7)
_cell_length_c                   17.8268(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.373(2)
_cell_angle_gamma                90
_cell_volume                     2016.17(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0757 before and 0.0454 after correction. 
The Ratio of minimum to maximum transmission is 0.9359. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50007
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.505
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             4167
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.8078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.69996(11) 0.98781(9) 0.37632(6) 0.0447(3) Uani 1 1 d . . . . .
O2 O 0.53198(9) 0.85762(7) 0.37884(4) 0.02114(19) Uani 1 1 d . . . . .
N1 N 0.46053(10) 0.90140(8) 0.30413(5) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.28575(11) 0.62476(8) 0.25437(6) 0.0197(2) Uani 1 1 d . . . . .
H2 H 0.3224(17) 0.5863(13) 0.2194(9) 0.038(4) Uiso 1 1 d . . . . .
C1 C 0.86609(15) 0.78937(11) 0.62325(7) 0.0282(3) Uani 1 1 d . . . . .
H1 H 0.914341 0.763458 0.671810 0.034 Uiso 1 1 calc R . . . .
C2 C 0.92302(14) 0.87492(11) 0.58788(7) 0.0267(3) Uani 1 1 d . . . . .
H2A H 1.010962 0.907567 0.611631 0.032 Uiso 1 1 calc R . . . .
C3 C 0.85167(13) 0.91311(11) 0.51765(7) 0.0255(3) Uani 1 1 d . . . . .
H3 H 0.890619 0.972418 0.493264 0.031 Uiso 1 1 calc R . . . .
C4 C 0.72355(13) 0.86547(10) 0.48249(7) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.66640(14) 0.77885(11) 0.51809(7) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.578519 0.745968 0.494477 0.030 Uiso 1 1 calc R . . . .
C6 C 0.73881(15) 0.74094(12) 0.58834(7) 0.0306(3) Uani 1 1 d . . . . .
H6 H 0.700829 0.681202 0.612770 0.037 Uiso 1 1 calc R . . . .
C7 C 0.65347(13) 0.91174(10) 0.40718(7) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.33140(13) 0.95524(10) 0.31986(7) 0.0213(3) Uani 1 1 d . . . . .
H8A H 0.275999 0.984598 0.271107 0.026 Uiso 1 1 calc R . . . .
H8B H 0.360664 1.019368 0.354080 0.026 Uiso 1 1 calc R . . . .
C9 C 0.23369(13) 0.88141(10) 0.35635(7) 0.0218(3) Uani 1 1 d . . . . .
H9A H 0.271961 0.874724 0.411957 0.026 Uiso 1 1 calc R . . . .
H9B H 0.137746 0.915223 0.349266 0.026 Uiso 1 1 calc R . . . .
C10 C 0.22342(12) 0.76934(10) 0.32038(6) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.12830(12) 0.67928(10) 0.32615(6) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.01130(13) 0.66522(11) 0.36163(7) 0.0246(3) Uani 1 1 d . . . . .
H12 H -0.020601 0.724491 0.389122 0.030 Uiso 1 1 calc R . . . .
C13 C -0.05668(14) 0.56382(12) 0.35591(8) 0.0302(3) Uani 1 1 d . . . . .
H13 H -0.135714 0.553215 0.380041 0.036 Uiso 1 1 calc R . . . .
C14 C -0.01109(14) 0.47639(11) 0.31515(8) 0.0302(3) Uani 1 1 d . . . . .
H14 H -0.059176 0.407131 0.312798 0.036 Uiso 1 1 calc R . . . .
C15 C 0.10182(13) 0.48797(11) 0.27825(7) 0.0255(3) Uani 1 1 d . . . . .
H15 H 0.131399 0.428565 0.249987 0.031 Uiso 1 1 calc R . . . .
C16 C 0.17072(12) 0.59032(10) 0.28412(7) 0.0203(3) Uani 1 1 d . . . . .
C17 C 0.31529(12) 0.73362(10) 0.27612(6) 0.0179(2) Uani 1 1 d . . . . .
C18 C 0.43016(12) 0.80254(10) 0.25263(6) 0.0185(3) Uani 1 1 d . . . . .
C19 C 0.56786(13) 0.73612(11) 0.25626(7) 0.0240(3) Uani 1 1 d . . . . .
H19A H 0.644337 0.786204 0.248415 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.552851 0.679182 0.216219 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.594422 0.700510 0.306482 0.036 Uiso 1 1 calc GR . . . .
C20 C 0.38278(12) 0.84991(10) 0.17149(6) 0.0189(2) Uani 1 1 d . . . . .
C21 C 0.45164(13) 0.94143(10) 0.14814(7) 0.0225(3) Uani 1 1 d . . . . .
H21 H 0.527326 0.975664 0.182922 0.027 Uiso 1 1 calc R . . . .
C22 C 0.41107(14) 0.98317(11) 0.07476(7) 0.0268(3) Uani 1 1 d . . . . .
H22 H 0.457782 1.046761 0.060006 0.032 Uiso 1 1 calc R . . . .
C23 C 0.30330(15) 0.93329(12) 0.02273(7) 0.0308(3) Uani 1 1 d . . . . .
H23 H 0.276170 0.961757 -0.027738 0.037 Uiso 1 1 calc R . . . .
C24 C 0.23580(15) 0.84172(13) 0.04510(7) 0.0339(3) Uani 1 1 d . . . . .
H24 H 0.162069 0.806481 0.009626 0.041 Uiso 1 1 calc R . . . .
C25 C 0.27437(14) 0.80039(11) 0.11894(7) 0.0265(3) Uani 1 1 d . . . . .
H25 H 0.226141 0.737599 0.133677 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.1988(15) . ?
O2 N1 1.4699(12) . ?
O2 C7 1.3423(14) . ?
N1 C8 1.4715(16) . ?
N1 C18 1.4970(15) . ?
N2 H2 0.902(16) . ?
N2 C16 1.3774(16) . ?
N2 C17 1.3811(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3757(19) . ?
C1 C6 1.3835(19) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3816(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3871(17) . ?
C4 C5 1.3886(17) . ?
C4 C7 1.4861(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3839(18) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5263(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4897(17) . ?
C10 C11 1.4333(17) . ?
C10 C17 1.3621(16) . ?
C11 C12 1.4011(17) . ?
C11 C16 1.4125(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3785(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3789(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3927(17) . ?
C17 C18 1.5020(16) . ?
C18 C19 1.5327(16) . ?
C18 C20 1.5379(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3899(17) . ?
C20 C25 1.3884(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.3838(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3816(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.3875(18) . ?
C25 H25 0.9500 . ?

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
C7 O2 N1 112.37(9) . . ?
O2 N1 C8 104.12(8) . . ?
O2 N1 C18 105.64(8) . . ?
C8 N1 C18 113.50(9) . . ?
C16 N2 H2 124.2(10) . . ?
C16 N2 C17 108.24(10) . . ?
C17 N2 H2 126.6(10) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.22(12) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.68(12) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.45(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.84(11) . . ?
C3 C4 C7 117.03(11) . . ?
C5 C4 C7 123.12(11) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.30(12) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.51(12) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 O2 124.84(11) . . ?
O1 C7 C4 123.99(11) . . ?
O2 C7 C4 111.17(10) . . ?
N1 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
N1 C8 C9 115.66(10) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 C8 109.80(10) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C11 C10 C9 130.11(11) . . ?
C17 C10 C9 122.71(11) . . ?
C17 C10 C11 107.13(11) . . ?
C12 C11 C10 134.41(12) . . ?
C12 C11 C16 119.13(11) . . ?
C16 C11 C10 106.45(10) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.79(12) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.00(12) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.77(12) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 121.4 . . ?
C14 C15 C16 117.26(13) . . ?
C16 C15 H15 121.4 . . ?
N2 C16 C11 108.12(10) . . ?
N2 C16 C15 129.85(12) . . ?
C15 C16 C11 122.02(12) . . ?
N2 C17 C18 124.57(10) . . ?
C10 C17 N2 110.05(11) . . ?
C10 C17 C18 125.37(11) . . ?
N1 C18 C17 109.47(9) . . ?
N1 C18 C19 109.15(9) . . ?
N1 C18 C20 105.49(9) . . ?
C17 C18 C19 111.76(10) . . ?
C17 C18 C20 111.78(9) . . ?
C19 C18 C20 108.98(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 120.44(10) . . ?
C25 C20 C18 121.18(11) . . ?
C25 C20 C21 118.34(11) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.67(12) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.65(12) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.5 . . ?
C24 C23 C22 119.04(12) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.66(12) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.64(12) . . ?
C24 C25 H25 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0872_tes_btm
_database_code_depnum_ccdc_archive 'CCDC 2060602'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H22 N2 O3), 0.5(C H2 Cl2)'
_chemical_formula_sum            'C44.50 H45 Cl N4 O6'
_chemical_formula_weight         767.29
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3351(7)
_cell_length_b                   13.1435(7)
_cell_length_c                   13.7758(7)
_cell_angle_alpha                93.491(2)
_cell_angle_beta                 101.268(2)
_cell_angle_gamma                116.875(2)
_cell_volume                     1925.16(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.788
_cell_measurement_theta_min      2.316
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 71753 reflections, Rint = 0.0610
 (33501 with I > 3sig(I), Rint = 0.0359)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             810
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6182
_reflns_number_total             7910
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         7910
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.2177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5442(9)
 0.4558(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N3-H3A = N1-H1
 0.88 with sigma of 0.02
 Cl2-C45 \\sim Cl1-C45
 with sigma of 0.005
4. Others
 Fixed Sof: Cl2(0.5) C45(0.5) H45A(0.5) H45B(0.5)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C31(H31), C33(H33)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C30(H30A,H30B), C32(H32A,H32B), C45(H45A,H45B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C40(H40), C41(H41), C42(H42),
  C43(H43), C44(H44)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C35(H35A,H35B,H35C), C38(H38A,H38B,
 H38C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.18269(16) 0.83302(15) 0.25699(12) 0.0199(4) Uani 1 1 d . . . . .
O2 O -0.04550(19) 0.62461(18) 0.10608(16) 0.0368(5) Uani 1 1 d . . . . .
O3 O 0.1138(2) 0.74249(19) 0.04540(16) 0.0383(6) Uani 1 1 d . . . . .
N1 N 0.2257(2) 0.80300(18) 0.61103(16) 0.0157(5) Uani 1 1 d D . . . .
H1 H 0.281(2) 0.780(2) 0.626(2) 0.019 Uiso 1 1 d DR . . . .
N2 N 0.1564(2) 0.84837(18) 0.35514(15) 0.0166(5) Uani 1 1 d . . . . .
C1 C 0.1660(2) 0.8270(2) 0.67689(19) 0.0158(5) Uani 1 1 d . . . . .
C2 C 0.1960(2) 0.8460(2) 0.78124(19) 0.0195(6) Uani 1 1 d . . . . .
H2 H 0.264046 0.837942 0.819011 0.023 Uiso 1 1 calc R . . . .
C3 C 0.1235(3) 0.8768(2) 0.8280(2) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.143191 0.891762 0.899315 0.028 Uiso 1 1 calc R . . . .
C4 C 0.0211(3) 0.8867(2) 0.7725(2) 0.0218(6) Uani 1 1 d . . . . .
H4 H -0.027000 0.908270 0.806907 0.026 Uiso 1 1 calc R . . . .
C5 C -0.0104(3) 0.8656(2) 0.6693(2) 0.0203(6) Uani 1 1 d . . . . .
H5 H -0.080420 0.871310 0.632430 0.024 Uiso 1 1 calc R . . . .
C6 C 0.0624(2) 0.8354(2) 0.61918(19) 0.0157(5) Uani 1 1 d . . . . .
C7 C 0.0630(2) 0.8149(2) 0.51622(18) 0.0143(5) Uani 1 1 d . . . . .
C8 C -0.0183(2) 0.8223(2) 0.42369(19) 0.0183(6) Uani 1 1 d . . . . .
H8A H -0.005470 0.902402 0.425355 0.022 Uiso 1 1 calc R . . . .
H8B H -0.107825 0.770215 0.419719 0.022 Uiso 1 1 calc R . . . .
C9 C 0.0178(2) 0.7865(2) 0.33388(18) 0.0164(5) Uani 1 1 d . . . . .
H9 H -0.012809 0.701097 0.323807 0.020 Uiso 1 1 calc R . . . .
C10 C -0.0200(3) 0.8215(2) 0.23487(19) 0.0201(6) Uani 1 1 d . . . . .
H10A H -0.017499 0.897766 0.245884 0.024 Uiso 1 1 calc R . . . .
H10B H -0.105120 0.763141 0.196042 0.024 Uiso 1 1 calc R . . . .
C11 C 0.0794(3) 0.8270(2) 0.18185(19) 0.0205(6) Uani 1 1 d . . . . .
H11 H 0.108593 0.896721 0.148423 0.025 Uiso 1 1 calc R . . . .
C12 C 0.0387(3) 0.7185(3) 0.1070(2) 0.0239(6) Uani 1 1 d . . . . .
C13 C 0.0924(4) 0.6447(3) -0.0251(3) 0.0596(11) Uani 1 1 d . . . . .
H13A H 0.005721 0.607690 -0.066286 0.089 Uiso 1 1 calc GR . . . .
H13B H 0.106515 0.588674 0.011998 0.089 Uiso 1 1 calc GR . . . .
H13C H 0.150406 0.671644 -0.068525 0.089 Uiso 1 1 calc GR . . . .
C14 C 0.1642(2) 0.7986(2) 0.51448(18) 0.0146(5) Uani 1 1 d . . . . .
C15 C 0.2151(2) 0.7923(2) 0.42453(18) 0.0142(5) Uani 1 1 d . . . . .
C16 C 0.3572(2) 0.8693(2) 0.45079(19) 0.0166(5) Uani 1 1 d . . . . .
H16A H 0.386277 0.878262 0.389001 0.025 Uiso 1 1 calc GR . . . .
H16B H 0.398001 0.833537 0.494092 0.025 Uiso 1 1 calc GR . . . .
H16C H 0.378528 0.945423 0.486129 0.025 Uiso 1 1 calc GR . . . .
C17 C 0.1790(2) 0.6679(2) 0.37952(18) 0.0141(5) Uani 1 1 d . . . . .
C18 C 0.2392(2) 0.6463(2) 0.31139(19) 0.0191(6) Uani 1 1 d . . . . .
H18 H 0.303656 0.709305 0.292061 0.023 Uiso 1 1 calc R . . . .
C19 C 0.2059(3) 0.5342(2) 0.2718(2) 0.0228(6) Uani 1 1 d . . . . .
H19 H 0.248101 0.520764 0.225778 0.027 Uiso 1 1 calc R . . . .
C20 C 0.1115(3) 0.4411(2) 0.2985(2) 0.0216(6) Uani 1 1 d . . . . .
H20 H 0.088716 0.364038 0.270859 0.026 Uiso 1 1 calc R . . . .
C21 C 0.0514(3) 0.4616(2) 0.3653(2) 0.0208(6) Uani 1 1 d . . . . .
H21 H -0.013218 0.398285 0.384140 0.025 Uiso 1 1 calc R . . . .
C22 C 0.0843(2) 0.5736(2) 0.40524(18) 0.0151(5) Uani 1 1 d . . . . .
H22 H 0.041486 0.586438 0.451020 0.018 Uiso 1 1 calc R . . . .
O4 O 0.36223(16) 0.70300(15) 0.78344(13) 0.0189(4) Uani 1 1 d . . . . .
O5 O 0.3400(2) 0.45952(19) 0.86491(15) 0.0383(6) Uani 1 1 d . . . . .
O6 O 0.34207(19) 0.60903(17) 0.95300(14) 0.0275(5) Uani 1 1 d . . . . .
N3 N 0.6639(2) 0.87485(18) 0.58248(16) 0.0160(5) Uani 1 1 d D . . . .
H3A H 0.710(2) 0.9472(16) 0.6141(18) 0.019 Uiso 1 1 d DR . . . .
N4 N 0.40472(19) 0.71037(18) 0.68983(15) 0.0161(5) Uani 1 1 d . . . . .
C23 C 0.6605(2) 0.8349(2) 0.48622(18) 0.0162(5) Uani 1 1 d . . . . .
C24 C 0.7292(2) 0.8928(2) 0.41998(19) 0.0188(6) Uani 1 1 d . . . . .
H24 H 0.790691 0.972028 0.438252 0.023 Uiso 1 1 calc R . . . .
C25 C 0.7046(3) 0.8310(2) 0.3271(2) 0.0218(6) Uani 1 1 d . . . . .
H25 H 0.749935 0.868625 0.280264 0.026 Uiso 1 1 calc R . . . .
C26 C 0.6142(3) 0.7138(2) 0.2995(2) 0.0211(6) Uani 1 1 d . . . . .
H26 H 0.601413 0.672877 0.235507 0.025 Uiso 1 1 calc R . . . .
C27 C 0.5439(2) 0.6574(2) 0.36416(19) 0.0182(6) Uani 1 1 d . . . . .
H27 H 0.481524 0.578562 0.344664 0.022 Uiso 1 1 calc R . . . .
C28 C 0.5657(2) 0.7184(2) 0.45955(18) 0.0152(5) Uani 1 1 d . . . . .
C29 C 0.5100(2) 0.6903(2) 0.54242(18) 0.0148(5) Uani 1 1 d . . . . .
C30 C 0.3982(2) 0.5827(2) 0.55169(18) 0.0168(6) Uani 1 1 d . . . . .
H30A H 0.408792 0.514014 0.534458 0.020 Uiso 1 1 calc R . . . .
H30B H 0.321290 0.573686 0.504930 0.020 Uiso 1 1 calc R . . . .
C31 C 0.3868(2) 0.5926(2) 0.65896(19) 0.0162(6) Uani 1 1 d . . . . .
H31 H 0.452774 0.580675 0.703892 0.019 Uiso 1 1 calc R . . . .
C32 C 0.2604(2) 0.5184(2) 0.6790(2) 0.0199(6) Uani 1 1 d . . . . .
H32A H 0.246857 0.439054 0.684768 0.024 Uiso 1 1 calc R . . . .
H32B H 0.191188 0.514358 0.625732 0.024 Uiso 1 1 calc R . . . .
C33 C 0.2717(2) 0.5832(2) 0.77854(19) 0.0180(6) Uani 1 1 d . . . . .
H33 H 0.188604 0.577143 0.781293 0.022 Uiso 1 1 calc R . . . .
C34 C 0.3216(3) 0.5413(2) 0.8687(2) 0.0230(6) Uani 1 1 d . . . . .
C35 C 0.3948(4) 0.5795(3) 1.0442(2) 0.0452(9) Uani 1 1 d . . . . .
H35A H 0.477036 0.587255 1.041918 0.068 Uiso 1 1 calc GR . . . .
H35B H 0.338488 0.499557 1.049314 0.068 Uiso 1 1 calc GR . . . .
H35C H 0.404311 0.631929 1.102721 0.068 Uiso 1 1 calc GR . . . .
C36 C 0.5713(2) 0.7872(2) 0.61517(18) 0.0148(5) Uani 1 1 d . . . . .
C37 C 0.5400(2) 0.8016(2) 0.71380(18) 0.0154(5) Uani 1 1 d . . . . .
C38 C 0.5439(2) 0.9186(2) 0.73509(19) 0.0178(6) Uani 1 1 d . . . . .
H38A H 0.495620 0.930558 0.675586 0.027 Uiso 1 1 calc GR . . . .
H38B H 0.631179 0.980249 0.751432 0.027 Uiso 1 1 calc GR . . . .
H38C H 0.507432 0.920296 0.791931 0.027 Uiso 1 1 calc GR . . . .
C39 C 0.6239(2) 0.7839(2) 0.80222(19) 0.0175(6) Uani 1 1 d . . . . .
C40 C 0.6972(2) 0.7328(2) 0.78698(19) 0.0189(6) Uani 1 1 d . . . . .
H40 H 0.697625 0.709501 0.720474 0.023 Uiso 1 1 calc R . . . .
C41 C 0.7698(3) 0.7152(2) 0.8678(2) 0.0245(6) Uani 1 1 d . . . . .
H41 H 0.819801 0.680186 0.856152 0.029 Uiso 1 1 calc R . . . .
C42 C 0.7700(3) 0.7478(3) 0.9641(2) 0.0293(7) Uani 1 1 d . . . . .
H42 H 0.818900 0.734515 1.019126 0.035 Uiso 1 1 calc R . . . .
C43 C 0.6989(3) 0.8003(3) 0.9808(2) 0.0348(8) Uani 1 1 d . . . . .
H43 H 0.699867 0.824412 1.047500 0.042 Uiso 1 1 calc R . . . .
C44 C 0.6259(3) 0.8177(3) 0.9001(2) 0.0275(7) Uani 1 1 d . . . . .
H44 H 0.576649 0.853273 0.912091 0.033 Uiso 1 1 calc R . . . .
Cl1 Cl 0.500000 1.000000 1.000000 0.0520(4) Uani 1 2 d DS T P . .
Cl2 Cl 0.50095(18) 0.86560(15) 1.14785(13) 0.0463(4) Uani 0.5 1 d D . . . .
C45 C 0.4131(6) 0.8781(5) 1.0417(4) 0.0459(18) Uani 0.5 1 d D . . . .
H45A H 0.383242 0.810030 0.989135 0.055 Uiso 0.5 1 calc R . . . .
H45B H 0.338811 0.880592 1.056371 0.055 Uiso 0.5 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.474(3) . ?
O1 C11 1.443(3) . ?
O2 C12 1.199(3) . ?
O3 C12 1.324(3) . ?
O3 C13 1.451(4) . ?
N1 H1 0.860(17) . ?
N1 C1 1.379(3) . ?
N1 C14 1.380(3) . ?
N2 C9 1.479(3) . ?
N2 C15 1.509(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.421(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.408(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(4) . ?
C6 C7 1.430(4) . ?
C7 C8 1.498(3) . ?
C7 C14 1.363(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.511(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.523(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.523(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.508(4) . ?
C15 C16 1.527(3) . ?
C15 C17 1.539(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.394(4) . ?
C17 C22 1.390(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9500 . ?
O4 N4 1.477(3) . ?
O4 C33 1.449(3) . ?
O5 C34 1.196(3) . ?
O6 C34 1.326(3) . ?
O6 C35 1.456(3) . ?
N3 H3A 0.885(17) . ?
N3 C23 1.382(3) . ?
N3 C36 1.381(3) . ?
N4 C31 1.483(3) . ?
N4 C37 1.503(3) . ?
C23 C24 1.391(4) . ?
C23 C28 1.411(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.374(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.404(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.377(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.407(4) . ?
C28 C29 1.429(4) . ?
C29 C30 1.499(3) . ?
C29 C36 1.370(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.515(3) . ?
C31 H31 1.0000 . ?
C31 C32 1.512(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.516(4) . ?
C33 H33 1.0000 . ?
C33 C34 1.522(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C37 1.507(4) . ?
C37 C38 1.525(3) . ?
C37 C39 1.539(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.385(4) . ?
C39 C44 1.385(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.388(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.368(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.380(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.387(4) . ?
C44 H44 0.9500 . ?
Cl1 C45 1.687(5) . ?
Cl1 C45 1.687(5) 2_677 ?
Cl2 C45 1.706(5) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?

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
C11 O1 N2 106.59(17) . . ?
C12 O3 C13 115.7(3) . . ?
C1 N1 H1 126.0(18) . . ?
C1 N1 C14 108.6(2) . . ?
C14 N1 H1 124.3(18) . . ?
O1 N2 C9 104.21(18) . . ?
O1 N2 C15 107.07(17) . . ?
C9 N2 C15 111.75(19) . . ?
N1 C1 C2 130.4(2) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 121.9(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.4(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.6(2) . . ?
C6 C7 C8 129.5(2) . . ?
C14 C7 C6 107.4(2) . . ?
C14 C7 C8 122.7(2) . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C7 C8 C9 107.8(2) . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
N2 C9 C8 107.5(2) . . ?
N2 C9 H9 109.7 . . ?
N2 C9 C10 101.9(2) . . ?
C8 C9 H9 109.7 . . ?
C8 C9 C10 117.9(2) . . ?
C10 C9 H9 109.7 . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.3 . . ?
C9 C10 C11 102.6(2) . . ?
H10A C10 H10B 109.2 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.3 . . ?
O1 C11 C10 107.4(2) . . ?
O1 C11 H11 110.3 . . ?
O1 C11 C12 103.9(2) . . ?
C10 C11 H11 110.3 . . ?
C12 C11 C10 114.4(2) . . ?
C12 C11 H11 110.3 . . ?
O2 C12 O3 124.9(3) . . ?
O2 C12 C11 125.3(3) . . ?
O3 C12 C11 109.7(2) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 123.0(2) . . ?
C7 C14 N1 109.9(2) . . ?
C7 C14 C15 126.6(2) . . ?
N2 C15 C16 107.72(19) . . ?
N2 C15 C17 113.22(19) . . ?
C14 C15 N2 100.80(19) . . ?
C14 C15 C16 110.5(2) . . ?
C14 C15 C17 113.2(2) . . ?
C16 C15 C17 111.0(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 121.2(2) . . ?
C22 C17 C15 120.7(2) . . ?
C22 C17 C18 118.1(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C33 O4 N4 107.03(17) . . ?
C34 O6 C35 114.8(2) . . ?
C23 N3 H3A 125.2(18) . . ?
C36 N3 H3A 125.7(18) . . ?
C36 N3 C23 108.6(2) . . ?
O4 N4 C31 103.96(17) . . ?
O4 N4 C37 108.02(17) . . ?
C31 N4 C37 112.77(19) . . ?
N3 C23 C24 130.0(2) . . ?
N3 C23 C28 107.7(2) . . ?
C24 C23 C28 122.3(2) . . ?
C23 C24 H24 121.3 . . ?
C25 C24 C23 117.4(2) . . ?
C25 C24 H24 121.3 . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.7(2) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.5 . . ?
C26 C27 C28 119.0(2) . . ?
C28 C27 H27 120.5 . . ?
C23 C28 C29 107.0(2) . . ?
C27 C28 C23 118.8(2) . . ?
C27 C28 C29 134.3(2) . . ?
C28 C29 C30 129.9(2) . . ?
C36 C29 C28 107.1(2) . . ?
C36 C29 C30 122.8(2) . . ?
C29 C30 H30A 110.0 . . ?
C29 C30 H30B 110.0 . . ?
C29 C30 C31 108.4(2) . . ?
H30A C30 H30B 108.4 . . ?
C31 C30 H30A 110.0 . . ?
C31 C30 H30B 110.0 . . ?
N4 C31 C30 107.9(2) . . ?
N4 C31 H31 109.8 . . ?
N4 C31 C32 101.1(2) . . ?
C30 C31 H31 109.8 . . ?
C32 C31 C30 118.0(2) . . ?
C32 C31 H31 109.8 . . ?
C31 C32 H32A 111.4 . . ?
C31 C32 H32B 111.4 . . ?
C31 C32 C33 101.8(2) . . ?
H32A C32 H32B 109.3 . . ?
C33 C32 H32A 111.4 . . ?
C33 C32 H32B 111.4 . . ?
O4 C33 C32 106.50(19) . . ?
O4 C33 H33 110.0 . . ?
O4 C33 C34 107.2(2) . . ?
C32 C33 H33 110.0 . . ?
C32 C33 C34 113.0(2) . . ?
C34 C33 H33 110.0 . . ?
O5 C34 O6 124.5(3) . . ?
O5 C34 C33 125.3(3) . . ?
O6 C34 C33 110.1(2) . . ?
O6 C35 H35A 109.5 . . ?
O6 C35 H35B 109.5 . . ?
O6 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N3 C36 C37 123.9(2) . . ?
C29 C36 N3 109.6(2) . . ?
C29 C36 C37 126.4(2) . . ?
N4 C37 C36 100.79(19) . . ?
N4 C37 C38 107.4(2) . . ?
N4 C37 C39 113.4(2) . . ?
C36 C37 C38 110.7(2) . . ?
C36 C37 C39 112.9(2) . . ?
C38 C37 C39 111.1(2) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C37 121.7(2) . . ?
C40 C39 C44 118.3(2) . . ?
C44 C39 C37 120.0(2) . . ?
C39 C40 H40 119.6 . . ?
C39 C40 C41 120.7(2) . . ?
C41 C40 H40 119.6 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.4(3) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 120.2 . . ?
C41 C42 C43 119.7(3) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.0(3) . . ?
C44 C43 H43 120.0 . . ?
C39 C44 C43 120.9(3) . . ?
C39 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C45 Cl1 C45 180.0(3) . 2_677 ?
Cl1 C45 Cl2 109.9(4) . . ?
Cl1 C45 H45A 109.7 . . ?
Cl1 C45 H45B 109.7 . . ?
Cl2 C45 H45A 109.7 . . ?
Cl2 C45 H45B 109.7 . . ?
H45A C45 H45B 108.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5442(9)
2 0.4558(9)

####################################################################### 
# 
# 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_0814_t
_database_code_depnum_ccdc_archive 'CCDC 2060605'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 O'
_chemical_formula_sum            'C19 H17 N3 O'
_chemical_formula_weight         303.35
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.5899(4)
_cell_length_b                   18.3551(8)
_cell_length_c                   10.2741(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.416(2)
_cell_angle_gamma                90
_cell_volume                     1582.02(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1009 before and 0.0544 after correction. 
The Ratio of minimum to maximum transmission is 0.9062.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.612
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3624
_reflns_number_total             4749
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.4548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1192
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1O-H1O_$1
 2.3 with sigma of 0.02
 O1-H1O
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.35999(9) 0.51291(5) 0.87552(8) 0.01557(18) Uani 1 1 d D . . . .
H1O H 0.3696(11) 0.5048(10) 0.9594(14) 0.045(5) Uiso 1 1 d D . . . .
N2 N 0.55715(14) 0.33441(6) 0.79267(11) 0.0244(2) Uani 1 1 d . . . . .
H3N H 0.387(2) 0.7226(10) 0.6613(16) 0.033(4) Uiso 1 1 d . . . . .
N3 N 0.35690(11) 0.67908(5) 0.62667(10) 0.0142(2) Uani 1 1 d . . . . .
N1 N 0.51726(11) 0.52110(5) 0.84596(9) 0.0125(2) Uani 1 1 d . . . . .
C1 C 0.54045(14) 0.39549(6) 0.77142(11) 0.0166(2) Uani 1 1 d . . . . .
C2 C 0.51745(14) 0.47220(6) 0.73062(11) 0.0134(2) Uani 1 1 d . . . . .
H2 H 0.611078 0.486417 0.692824 0.016 Uiso 1 1 calc R . . . .
C3 C 0.36907(14) 0.47943(6) 0.61771(11) 0.0145(2) Uani 1 1 d . . . . .
H3A H 0.386900 0.454798 0.536434 0.017 Uiso 1 1 calc R . . . .
H3B H 0.276143 0.456519 0.644039 0.017 Uiso 1 1 calc R . . . .
C4 C 0.33883(13) 0.55847(6) 0.59136(11) 0.0123(2) Uani 1 1 d . . . . .
C5 C 0.22648(13) 0.59333(6) 0.48687(11) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.11249(14) 0.56801(7) 0.37736(12) 0.0180(2) Uani 1 1 d . . . . .
H6 H 0.099476 0.517315 0.359680 0.022 Uiso 1 1 calc R . . . .
C7 C 0.01985(16) 0.61827(7) 0.29604(13) 0.0236(3) Uani 1 1 d . . . . .
H7 H -0.057475 0.601866 0.221271 0.028 Uiso 1 1 calc R . . . .
C8 C 0.03752(16) 0.69322(7) 0.32153(13) 0.0250(3) Uani 1 1 d . . . . .
H8 H -0.027834 0.726552 0.263343 0.030 Uiso 1 1 calc R . . . .
C9 C 0.14787(15) 0.71971(7) 0.42939(13) 0.0208(3) Uani 1 1 d . . . . .
H9 H 0.159146 0.770495 0.446693 0.025 Uiso 1 1 calc R . . . .
C10 C 0.24184(13) 0.66901(6) 0.51165(11) 0.0148(2) Uani 1 1 d . . . . .
C11 C 0.41419(13) 0.61172(6) 0.67393(11) 0.0117(2) Uani 1 1 d . . . . .
C12 C 0.53506(13) 0.59914(6) 0.80181(11) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.50912(14) 0.65094(6) 0.91148(12) 0.0163(2) Uani 1 1 d . . . . .
H13A H 0.399592 0.645969 0.923743 0.024 Uiso 1 1 calc GR . . . .
H13B H 0.527211 0.701199 0.886121 0.024 Uiso 1 1 calc GR . . . .
H13C H 0.583919 0.638905 0.994970 0.024 Uiso 1 1 calc GR . . . .
C14 C 0.70757(13) 0.60580(6) 0.78509(11) 0.0135(2) Uani 1 1 d . . . . .
C15 C 0.74357(14) 0.63424(6) 0.66931(12) 0.0150(2) Uani 1 1 d . . . . .
H15 H 0.659977 0.651229 0.599790 0.018 Uiso 1 1 calc R . . . .
C16 C 0.90059(14) 0.63805(6) 0.65434(12) 0.0173(2) Uani 1 1 d . . . . .
H16 H 0.923651 0.657210 0.574679 0.021 Uiso 1 1 calc R . . . .
C17 C 1.02363(14) 0.61379(7) 0.75600(13) 0.0191(3) Uani 1 1 d . . . . .
H17 H 1.130748 0.615464 0.745418 0.023 Uiso 1 1 calc R . . . .
C18 C 0.98940(14) 0.58724(7) 0.87254(12) 0.0191(3) Uani 1 1 d . . . . .
H18 H 1.073571 0.571553 0.942814 0.023 Uiso 1 1 calc R . . . .
C19 C 0.83278(14) 0.58332(7) 0.88765(12) 0.0169(2) Uani 1 1 d . . . . .
H19 H 0.810659 0.565217 0.968393 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1O 0.861(14) . ?
O1 N1 1.4548(12) . ?
N2 C1 1.1454(16) . ?
N3 H3N 0.890(18) . ?
N3 C10 1.3803(15) . ?
N3 C11 1.3798(14) . ?
N1 C2 1.4869(14) . ?
N1 C12 1.5203(14) . ?
C1 C2 1.4701(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.5336(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.4884(15) . ?
C4 C5 1.4310(15) . ?
C4 C11 1.3631(15) . ?
C5 C6 1.4024(16) . ?
C5 C10 1.4132(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3772(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.4026(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3824(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3924(16) . ?
C11 C12 1.5069(15) . ?
C12 C13 1.5268(15) . ?
C12 C14 1.5329(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3933(16) . ?
C14 C19 1.3964(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3917(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3898(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3816(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3889(17) . ?
C19 H19 0.9500 . ?

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
N1 O1 H1O 109.5(7) . . ?
C10 N3 H3N 123.7(11) . . ?
C11 N3 H3N 127.8(11) . . ?
C11 N3 C10 108.47(9) . . ?
O1 N1 C2 105.32(8) . . ?
O1 N1 C12 108.48(8) . . ?
C2 N1 C12 108.28(8) . . ?
N2 C1 C2 174.53(13) . . ?
N1 C2 H2 106.9 . . ?
N1 C2 C3 114.05(9) . . ?
C1 C2 N1 111.96(9) . . ?
C1 C2 H2 106.9 . . ?
C1 C2 C3 109.72(9) . . ?
C3 C2 H2 106.9 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.83(9) . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C5 C4 C3 129.45(10) . . ?
C11 C4 C3 123.01(10) . . ?
C11 C4 C5 107.44(10) . . ?
C6 C5 C4 134.07(11) . . ?
C6 C5 C10 119.49(10) . . ?
C10 C5 C4 106.41(10) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.51(11) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.24(12) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.51(12) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.36(12) . . ?
C10 C9 H9 121.3 . . ?
N3 C10 C5 107.93(10) . . ?
N3 C10 C9 130.17(11) . . ?
C9 C10 C5 121.88(11) . . ?
N3 C11 C12 124.81(10) . . ?
C4 C11 N3 109.74(10) . . ?
C4 C11 C12 125.37(10) . . ?
N1 C12 C13 109.06(9) . . ?
N1 C12 C14 105.67(8) . . ?
C11 C12 N1 108.05(8) . . ?
C11 C12 C13 111.44(9) . . ?
C11 C12 C14 113.05(9) . . ?
C13 C12 C14 109.33(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 121.52(10) . . ?
C15 C14 C19 118.59(11) . . ?
C19 C14 C12 119.88(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.76(11) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.95(11) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.68(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.45(11) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.52(11) . . ?
C18 C19 H19 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0812_t
_database_code_depnum_ccdc_archive 'CCDC 2060604'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5841(6)
_cell_length_b                   10.1481(7)
_cell_length_c                   10.2458(8)
_cell_angle_alpha                112.745(2)
_cell_angle_beta                 103.325(2)
_cell_angle_gamma                99.118(2)
_cell_volume                     769.88(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0980 before and 0.0565 after correction. 
The Ratio of minimum to maximum transmission is 0.8989.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28347
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.614
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             3937
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A
 0.84 with sigma of 0.01
 H1-H1_$1
 2.3 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.34820(11) 0.45980(10) 0.85797(11) 0.0157(2) Uani 1 1 d . . . . .
H1 H 0.3640(13) 0.481(2) 0.951(2) 0.055(6) Uiso 1 1 d D . . . .
N1 N 0.24270(13) 0.12535(12) 0.45467(12) 0.0142(2) Uani 1 1 d D . . . .
H1A H 0.248(2) 0.0420(12) 0.4535(19) 0.025(4) Uiso 1 1 d D . . . .
N2 N 0.50237(13) 0.44815(12) 0.82180(11) 0.0130(2) Uani 1 1 d . . . . .
C1 C 0.12990(16) 0.14615(14) 0.34894(14) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.00418(17) 0.04307(15) 0.21827(15) 0.0189(3) Uani 1 1 d . . . . .
H2 H -0.013479 -0.060807 0.186936 0.023 Uiso 1 1 calc R . . . .
C3 C -0.09376(18) 0.09805(16) 0.13612(15) 0.0224(3) Uani 1 1 d . . . . .
H3 H -0.180949 0.030430 0.046994 0.027 Uiso 1 1 calc R . . . .
C4 C -0.06746(18) 0.25107(16) 0.18119(15) 0.0219(3) Uani 1 1 d . . . . .
H4 H -0.137430 0.285199 0.122524 0.026 Uiso 1 1 calc R . . . .
C5 C 0.05853(17) 0.35317(15) 0.30953(15) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.076139 0.456797 0.339173 0.022 Uiso 1 1 calc R . . . .
C6 C 0.15995(16) 0.30070(14) 0.39520(14) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.29655(15) 0.37221(14) 0.53209(13) 0.0132(3) Uani 1 1 d . . . . .
C8 C 0.37806(16) 0.53311(14) 0.63119(14) 0.0153(3) Uani 1 1 d . . . . .
H8A H 0.298873 0.579567 0.676766 0.018 Uiso 1 1 calc R . . . .
H8B H 0.410389 0.583210 0.571688 0.018 Uiso 1 1 calc R . . . .
C9 C 0.53211(16) 0.55247(14) 0.75364(14) 0.0142(3) Uani 1 1 d . . . . .
H9 H 0.618407 0.526476 0.704759 0.017 Uiso 1 1 calc R . . . .
C10 C 0.60397(18) 0.71254(15) 0.87057(15) 0.0200(3) Uani 1 1 d . . . . .
H10A H 0.519217 0.746061 0.914675 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.638796 0.775012 0.823888 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.700429 0.720161 0.948846 0.030 Uiso 1 1 calc GR . . . .
C11 C 0.47168(15) 0.29018(14) 0.70662(13) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.34174(15) 0.26384(14) 0.56557(14) 0.0125(2) Uani 1 1 d . . . . .
C13 C 0.41627(17) 0.18125(14) 0.76724(14) 0.0164(3) Uani 1 1 d . . . . .
H13A H 0.498304 0.206982 0.863578 0.025 Uiso 1 1 calc GR . . . .
H13B H 0.407287 0.080014 0.696445 0.025 Uiso 1 1 calc GR . . . .
H13C H 0.307680 0.186885 0.780576 0.025 Uiso 1 1 calc GR . . . .
C14 C 0.64155(15) 0.27825(13) 0.68584(14) 0.0128(3) Uani 1 1 d . . . . .
C15 C 0.78191(16) 0.32537(15) 0.81069(14) 0.0163(3) Uani 1 1 d . . . . .
H15 H 0.771162 0.362331 0.907724 0.020 Uiso 1 1 calc R . . . .
C16 C 0.93742(16) 0.31867(15) 0.79429(15) 0.0180(3) Uani 1 1 d . . . . .
H16 H 1.032202 0.352130 0.880133 0.022 Uiso 1 1 calc R . . . .
C17 C 0.95466(16) 0.26325(15) 0.65288(15) 0.0176(3) Uani 1 1 d . . . . .
H17 H 1.061003 0.259506 0.641898 0.021 Uiso 1 1 calc R . . . .
C18 C 0.81591(16) 0.21357(14) 0.52825(15) 0.0161(3) Uani 1 1 d . . . . .
H18 H 0.826757 0.174571 0.431290 0.019 Uiso 1 1 calc R . . . .
C19 C 0.65988(16) 0.22064(14) 0.54466(14) 0.0141(3) Uani 1 1 d . . . . .
H19 H 0.565151 0.185712 0.458454 0.017 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.86(2) . ?
O1 N2 1.4644(13) . ?
N1 H1A 0.850(9) . ?
N1 C1 1.3833(17) . ?
N1 C12 1.3893(16) . ?
N2 C9 1.4973(16) . ?
N2 C11 1.5139(16) . ?
C1 C2 1.3945(18) . ?
C1 C6 1.4113(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.4028(18) . ?
C6 C7 1.4331(18) . ?
C7 C8 1.4883(17) . ?
C7 C12 1.3577(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5243(18) . ?
C9 H9 1.0000 . ?
C9 C10 1.5137(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5059(17) . ?
C11 C13 1.5279(17) . ?
C11 C14 1.5380(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3967(18) . ?
C14 C19 1.3925(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3922(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3901(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3835(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.3972(17) . ?
C19 H19 0.9500 . ?

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 O1 H1 110.7(8) . . ?
C1 N1 H1A 125.6(11) . . ?
C1 N1 C12 108.46(11) . . ?
C12 N1 H1A 125.9(11) . . ?
O1 N2 C9 106.12(9) . . ?
O1 N2 C11 107.41(9) . . ?
C9 N2 C11 109.43(9) . . ?
N1 C1 C2 130.51(12) . . ?
N1 C1 C6 107.53(11) . . ?
C2 C1 C6 121.96(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.36(13) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.56(13) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.09(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.64(13) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C7 106.94(11) . . ?
C5 C6 C1 119.37(12) . . ?
C5 C6 C7 133.67(12) . . ?
C6 C7 C8 130.13(12) . . ?
C12 C7 C6 107.34(11) . . ?
C12 C7 C8 122.49(11) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C9 109.98(10) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N2 C9 C8 112.73(10) . . ?
N2 C9 H9 106.6 . . ?
N2 C9 C10 111.98(10) . . ?
C8 C9 H9 106.6 . . ?
C10 C9 C8 111.78(11) . . ?
C10 C9 H9 106.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C13 109.87(10) . . ?
N2 C11 C14 105.52(9) . . ?
C12 C11 N2 108.53(10) . . ?
C12 C11 C13 111.39(10) . . ?
C12 C11 C14 113.00(10) . . ?
C13 C11 C14 108.35(10) . . ?
N1 C12 C11 125.12(11) . . ?
C7 C12 N1 109.71(11) . . ?
C7 C12 C11 125.05(11) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 119.81(11) . . ?
C19 C14 C11 121.67(11) . . ?
C19 C14 C15 118.52(11) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.63(12) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.31(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.56(12) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.15(12) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.80(12) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0953_tlc_snyder_2
_database_code_depnum_ccdc_archive 'CCDC 2060603'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2020-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6219)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 Br N2 O2'
_chemical_formula_sum            'C25 H21 Br N2 O2'
_chemical_formula_weight         461.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8948(6)
_cell_length_b                   10.3781(6)
_cell_length_c                   20.5618(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2111.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0841 before and 0.0740 after correction. 
The Ratio of minimum to maximum transmission is 0.8901.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43364
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.723
_diffrn_reflns_theta_min         2.198
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4699
_reflns_number_total             5432
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1781 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.0802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 1.01355(2) 0.09626(3) 0.58983(2) 0.02565(9) Uani 1 1 d . . . . .
N1 N 0.5321(2) 0.6189(2) 0.64081(10) 0.0163(5) Uani 1 1 d . . . . .
H1 H 0.593(3) 0.626(3) 0.6719(15) 0.020 Uiso 1 1 d . U . . .
N2 N 0.3748(2) 0.2879(2) 0.64452(11) 0.0161(5) Uani 1 1 d . . . . .
O1 O 0.25098(17) 0.32326(17) 0.67962(9) 0.0158(4) Uani 1 1 d . . . . .
O2 O 0.29941(19) 0.15674(16) 0.74671(9) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.8525(3) 0.1865(3) 0.61128(13) 0.0175(6) Uani 1 1 d . . . . .
C2 C 0.8302(3) 0.3080(3) 0.58663(14) 0.0199(6) Uani 1 1 d . . . . .
H2 H 0.895655 0.348442 0.559697 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7099(3) 0.3706(3) 0.60192(13) 0.0185(6) Uani 1 1 d . . . . .
H3 H 0.693007 0.453978 0.584714 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6147(3) 0.3135(3) 0.64170(13) 0.0146(6) Uani 1 1 d . . . . .
C5 C 0.6404(3) 0.1909(3) 0.66568(14) 0.0211(6) Uani 1 1 d . . . . .
H5 H 0.575272 0.150440 0.692806 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7585(3) 0.1268(3) 0.65091(14) 0.0208(6) Uani 1 1 d . . . . .
H6 H 0.775019 0.042940 0.667687 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4833(3) 0.3820(2) 0.66203(11) 0.0143(5) Uani 1 1 d . . . . .
C8 C 0.4871(3) 0.4029(2) 0.73606(12) 0.0171(5) Uani 1 1 d . . . . .
H8A H 0.402386 0.442933 0.750250 0.026 Uiso 1 1 calc R U . . .
H8B H 0.563071 0.459360 0.747155 0.026 Uiso 1 1 calc R U . . .
H8C H 0.498280 0.319699 0.757949 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4605(3) 0.5080(2) 0.62733(12) 0.0146(5) Uani 1 1 d . . . . .
C10 C 0.4844(3) 0.7161(2) 0.60092(11) 0.0178(5) Uani 1 1 d . . . . .
C11 C 0.5234(3) 0.8443(2) 0.59733(13) 0.0218(6) Uani 1 1 d . . . . .
H11 H 0.593963 0.877482 0.623805 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4554(4) 0.9215(3) 0.55375(15) 0.0336(8) Uani 1 1 d . . . . .
H12 H 0.478910 1.009979 0.550189 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3527(4) 0.8717(3) 0.51483(17) 0.0405(9) Uani 1 1 d . . . . .
H13 H 0.307446 0.927480 0.485366 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3148(3) 0.7443(3) 0.51773(15) 0.0307(7) Uani 1 1 d . . . . .
H14 H 0.245099 0.711948 0.490450 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3812(3) 0.6636(3) 0.56178(13) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.3692(3) 0.5305(3) 0.57949(13) 0.0166(6) Uani 1 1 d . . . . .
C17 C 0.2776(3) 0.4269(3) 0.55458(14) 0.0199(6) Uani 1 1 d . . . . .
H17A H 0.271873 0.431254 0.506559 0.024 Uiso 1 1 calc R U . . .
H17B H 0.185641 0.438149 0.572637 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3353(3) 0.2969(3) 0.57547(13) 0.0194(6) Uani 1 1 d . . . . .
H18A H 0.267173 0.229454 0.566397 0.023 Uiso 1 1 calc R U . . .
H18B H 0.415637 0.278027 0.548372 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2245(3) 0.2418(2) 0.72932(13) 0.0160(6) Uani 1 1 d . . . . .
C20 C 0.0935(3) 0.2716(3) 0.76107(13) 0.0174(6) Uani 1 1 d . . . . .
C21 C 0.0037(3) 0.3631(2) 0.73666(13) 0.0205(6) Uani 1 1 d . . . . .
H21 H 0.026803 0.411312 0.698991 0.025 Uiso 1 1 calc R U . . .
C22 C -0.1180(3) 0.3837(3) 0.76699(15) 0.0241(6) Uani 1 1 d . . . . .
H22 H -0.179392 0.445345 0.749862 0.029 Uiso 1 1 calc R U . . .
C23 C -0.1520(3) 0.3148(3) 0.82255(16) 0.0276(7) Uani 1 1 d . . . . .
H23 H -0.236519 0.329074 0.843229 0.033 Uiso 1 1 calc R U . . .
C24 C -0.0631(3) 0.2260(3) 0.84757(16) 0.0331(8) Uani 1 1 d . . . . .
H24 H -0.085901 0.179368 0.885791 0.040 Uiso 1 1 calc R U . . .
C25 C 0.0598(3) 0.2042(3) 0.81718(15) 0.0260(7) Uani 1 1 d . . . . .
H25 H 0.121207 0.143028 0.834738 0.031 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
Br1 C1 1.900(3) . ?
N1 H1 0.88(3) . ?
N1 C9 1.379(3) . ?
N1 C10 1.383(3) . ?
N2 O1 1.468(3) . ?
N2 C7 1.496(3) . ?
N2 C18 1.475(4) . ?
O1 C19 1.352(3) . ?
O2 C19 1.207(3) . ?
C1 C2 1.378(4) . ?
C1 C6 1.383(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 C5 1.387(4) . ?
C4 C7 1.540(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.538(3) . ?
C7 C9 1.506(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C16 1.356(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.410(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(4) . ?
C15 C16 1.434(4) . ?
C16 C17 1.497(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.526(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.484(4) . ?
C20 C21 1.393(4) . ?
C20 C25 1.390(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(4) . ?
C25 H25 0.9500 . ?

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
C9 N1 H1 124.5(19) . . ?
C9 N1 C10 108.3(2) . . ?
C10 N1 H1 127.0(19) . . ?
O1 N2 C7 108.50(19) . . ?
O1 N2 C18 103.68(19) . . ?
C18 N2 C7 112.3(2) . . ?
C19 O1 N2 112.14(19) . . ?
C2 C1 Br1 120.0(2) . . ?
C2 C1 C6 121.3(2) . . ?
C6 C1 Br1 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 C7 122.6(2) . . ?
C5 C4 C7 118.8(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C4 103.81(18) . . ?
N2 C7 C8 110.4(2) . . ?
N2 C7 C9 110.2(2) . . ?
C8 C7 C4 108.2(2) . . ?
C9 C7 C4 113.5(2) . . ?
C9 C7 C8 110.5(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C7 123.5(2) . . ?
C16 C9 N1 110.2(2) . . ?
C16 C9 C7 126.3(2) . . ?
N1 C10 C11 129.5(3) . . ?
N1 C10 C15 107.7(2) . . ?
C11 C10 C15 122.8(2) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.0 . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C16 106.7(2) . . ?
C14 C15 C10 118.7(3) . . ?
C14 C15 C16 134.7(3) . . ?
C9 C16 C15 107.1(3) . . ?
C9 C16 C17 121.9(2) . . ?
C15 C16 C17 131.0(3) . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
C16 C17 C18 108.2(2) . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
N2 C18 C17 115.2(2) . . ?
N2 C18 H18A 108.5 . . ?
N2 C18 H18B 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
O1 C19 C20 111.8(2) . . ?
O2 C19 O1 124.2(3) . . ?
O2 C19 C20 124.0(3) . . ?
C21 C20 C19 122.7(3) . . ?
C25 C20 C19 118.0(2) . . ?
C25 C20 C21 119.3(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.2(3) . . ?
C24 C25 H25 119.9 . . ?

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
Br1 C1 C2 C3 178.5(2) . . . . ?
Br1 C1 C6 C5 -178.9(2) . . . . ?
N1 C9 C16 C15 -0.9(3) . . . . ?
N1 C9 C16 C17 179.6(2) . . . . ?
N1 C10 C11 C12 -178.3(3) . . . . ?
N1 C10 C15 C14 178.9(3) . . . . ?
N1 C10 C15 C16 -0.3(3) . . . . ?
N2 O1 C19 O2 6.1(3) . . . . ?
N2 O1 C19 C20 -175.3(2) . . . . ?
N2 C7 C9 N1 170.3(2) . . . . ?
N2 C7 C9 C16 -9.6(3) . . . . ?
O1 N2 C7 C4 162.3(2) . . . . ?
O1 N2 C7 C8 46.5(3) . . . . ?
O1 N2 C7 C9 -75.8(2) . . . . ?
O1 N2 C18 C17 55.7(3) . . . . ?
O1 C19 C20 C21 7.0(4) . . . . ?
O1 C19 C20 C25 -173.4(2) . . . . ?
O2 C19 C20 C21 -174.4(3) . . . . ?
O2 C19 C20 C25 5.2(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 C7 177.3(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C7 N2 127.6(3) . . . . ?
C3 C4 C7 C8 -115.2(3) . . . . ?
C3 C4 C7 C9 7.9(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C7 C9 N1 -73.8(3) . . . . ?
C4 C7 C9 C16 106.4(3) . . . . ?
C5 C4 C7 N2 -54.3(3) . . . . ?
C5 C4 C7 C8 63.0(3) . . . . ?
C5 C4 C7 C9 -173.9(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 N2 O1 C19 -106.3(2) . . . . ?
C7 N2 C18 C17 -61.2(3) . . . . ?
C7 C4 C5 C6 -177.7(3) . . . . ?
C7 C9 C16 C15 179.0(2) . . . . ?
C7 C9 C16 C17 -0.5(4) . . . . ?
C8 C7 C9 N1 48.1(3) . . . . ?
C8 C7 C9 C16 -131.8(3) . . . . ?
C9 N1 C10 C11 179.0(3) . . . . ?
C9 N1 C10 C15 -0.2(3) . . . . ?
C9 C16 C17 C18 -17.3(3) . . . . ?
C10 N1 C9 C7 -179.2(2) . . . . ?
C10 N1 C9 C16 0.7(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C10 C15 C16 C9 0.8(3) . . . . ?
C10 C15 C16 C17 -179.8(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C11 C10 C15 C16 -179.6(2) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C13 C14 C15 C16 178.6(3) . . . . ?
C14 C15 C16 C9 -178.3(3) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
C15 C10 C11 C12 0.7(4) . . . . ?
C15 C16 C17 C18 163.4(3) . . . . ?
C16 C17 C18 N2 47.8(3) . . . . ?
C18 N2 O1 C19 134.1(2) . . . . ?
C18 N2 C7 C4 -83.7(2) . . . . ?
C18 N2 C7 C8 160.6(2) . . . . ?
C18 N2 C7 C9 38.2(3) . . . . ?
C19 C20 C21 C22 177.9(3) . . . . ?
C19 C20 C25 C24 -178.2(3) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C20 C25 C24 1.4(4) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 -0.5(5) . . . . ?
C23 C24 C25 C20 -0.3(5) . . . . ?
C25 C20 C21 C22 -1.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_0869_tessa_top
_database_code_depnum_ccdc_archive 'CCDC 2060606'
loop_
_audit_author_name
_audit_author_address
'Alexander S. Filatov'
;the University of Chicago
United States of America
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O3, 0.15(H2 O)'
_chemical_formula_sum            'C22 H22.30 N2 O3.15'
_chemical_formula_weight         365.12
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   20.9936(14)
_cell_length_b                   10.3069(7)
_cell_length_c                   17.3090(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.457(2)
_cell_angle_gamma                90
_cell_volume                     3694.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1064 before and 0.0579 after correction. 
The Ratio of minimum to maximum transmission is 0.8948.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1548
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            96894
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_min         2.207
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            CMOS
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus X-ray tube'
_diffrn_source_type              'INCOATEC ImuS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5440
_reflns_number_total             7298
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material  
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         7298
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      8.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+2.2164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N3-H3 = N1-H1
 0.88 with sigma of 0.02
3. Others
 Fixed Sof: O7(0.3) H7A(0.3) H7B(0.3)
4.a Free rotating group:
 O7(H7A,H7B)
4.b Ternary CH refined with riding coordinates:
 C18(H18), C20(H20), C40(H40), C42(H42)
4.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C39(H39A,H39B), C41(H41A,H41B)
4.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C24(H24), C25(H25), C26(H26), C27(H27), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C44(H44A,H44B,
 H44C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.43371(5) 0.67226(12) 0.67381(7) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.31551(7) 0.7245(2) 0.51466(9) 0.0702(6) Uani 1 1 d . . . . .
O3 O 0.42281(6) 0.72594(14) 0.52500(7) 0.0373(3) Uani 1 1 d . . . . .
O7 O 0.1576(3) 0.7332(6) 0.6696(4) 0.0631(15) Uiso 0.3 1 d . . P . .
H7A H 0.138118 0.802314 0.682682 0.095 Uiso 0.3 1 d G . P . .
H7B H 0.199159 0.746207 0.677811 0.095 Uiso 0.3 1 d G . P . .
N1 N 0.44407(7) 0.30451(13) 0.85181(8) 0.0199(3) Uani 1 1 d D . . . .
H1 H 0.4817(7) 0.2681(17) 0.8482(10) 0.024 Uiso 1 1 d DR . . . .
N2 N 0.41427(6) 0.60844(13) 0.74285(8) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.39904(8) 0.25511(17) 0.89345(9) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.40213(9) 0.14691(18) 0.94204(10) 0.0279(4) Uani 1 1 d . . . . .
H2 H 0.439688 0.094146 0.951934 0.034 Uiso 1 1 calc R . . . .
C3 C 0.34786(10) 0.1196(2) 0.97539(11) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.348023 0.045306 1.007930 0.042 Uiso 1 1 calc DR . . . .
C4 C 0.29302(9) 0.1984(2) 0.96237(11) 0.0368(5) Uani 1 1 d . . . . .
H4 H 0.256795 0.177014 0.986322 0.044 Uiso 1 1 calc R . . . .
C5 C 0.29064(8) 0.3065(2) 0.91544(10) 0.0316(4) Uani 1 1 d . . . . .
H5 H 0.253528 0.360672 0.907826 0.038 Uiso 1 1 calc R . . . .
C6 C 0.34389(8) 0.33551(17) 0.87894(9) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.35725(8) 0.43477(17) 0.82604(10) 0.0230(4) Uani 1 1 d . . . . .
C8 C 0.41808(7) 0.41196(16) 0.81089(9) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.45290(7) 0.48629(15) 0.75567(9) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.45394(8) 0.40433(17) 0.68172(10) 0.0236(4) Uani 1 1 d . . . . .
H10A H 0.410191 0.373610 0.661557 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.482663 0.329735 0.694655 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.469646 0.457384 0.641780 0.035 Uiso 1 1 calc GR . . . .
C11 C 0.52097(7) 0.52614(15) 0.79489(9) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.53400(8) 0.55189(16) 0.87478(10) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.500546 0.543019 0.905298 0.026 Uiso 1 1 calc R . . . .
C13 C 0.59489(8) 0.59020(16) 0.91055(10) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.603160 0.606109 0.965345 0.031 Uiso 1 1 calc R . . . .
C14 C 0.64379(8) 0.60538(16) 0.86650(11) 0.0272(4) Uani 1 1 d . . . . .
H14 H 0.685668 0.631490 0.890981 0.033 Uiso 1 1 calc R . . . .
C15 C 0.63151(8) 0.58253(17) 0.78730(11) 0.0265(4) Uani 1 1 d . . . . .
H15 H 0.664748 0.594546 0.756777 0.032 Uiso 1 1 calc R . . . .
C16 C 0.57063(8) 0.54188(16) 0.75163(10) 0.0223(4) Uani 1 1 d . . . . .
H16 H 0.562863 0.524628 0.696976 0.027 Uiso 1 1 calc R . . . .
C17 C 0.31594(8) 0.54313(18) 0.78817(10) 0.0259(4) Uani 1 1 d . . . . .
H17A H 0.315659 0.615988 0.825379 0.031 Uiso 1 1 calc R . . . .
H17B H 0.270994 0.512828 0.771857 0.031 Uiso 1 1 calc R . . . .
C18 C 0.34422(8) 0.58662(17) 0.71764(10) 0.0236(4) Uani 1 1 d . . . . .
H18 H 0.337250 0.518127 0.676189 0.028 Uiso 1 1 calc R . . . .
C19 C 0.32385(8) 0.71735(18) 0.68221(11) 0.0295(4) Uani 1 1 d . . . . .
H19A H 0.318652 0.781631 0.723220 0.035 Uiso 1 1 calc R . . . .
H19B H 0.282907 0.710887 0.644774 0.035 Uiso 1 1 calc R . . . .
C20 C 0.37981(8) 0.75289(17) 0.64072(10) 0.0256(4) Uani 1 1 d . . . . .
H20 H 0.391465 0.845901 0.651757 0.031 Uiso 1 1 calc R . . . .
C21 C 0.36760(9) 0.73206(18) 0.55367(11) 0.0334(5) Uani 1 1 d . . . . .
C22 C 0.41708(11) 0.7209(2) 0.44049(11) 0.0437(5) Uani 1 1 d . . . . .
H22A H 0.399625 0.803372 0.418028 0.066 Uiso 1 1 calc GR . . . .
H22B H 0.387990 0.650052 0.420113 0.066 Uiso 1 1 calc GR . . . .
H22C H 0.459744 0.706023 0.426163 0.066 Uiso 1 1 calc GR . . . .
O4 O 0.08311(5) 0.66537(12) 0.31152(7) 0.0305(3) Uani 1 1 d . . . . .
O5 O 0.08749(7) 0.78316(14) 0.44767(8) 0.0392(3) Uani 1 1 d . . . . .
O6 O 0.18858(6) 0.85341(15) 0.44703(9) 0.0482(4) Uani 1 1 d . . . . .
N3 N 0.04841(7) 0.27744(15) 0.15005(8) 0.0249(3) Uani 1 1 d D . . . .
H3A H 0.0081(10) 0.2725(19) 0.1375(11) 0.030 Uiso 1 1 d R . . . .
N4 N 0.10390(6) 0.56963(14) 0.25800(8) 0.0257(3) Uani 1 1 d . . . . .
C23 C 0.09150(8) 0.19285(18) 0.12497(10) 0.0252(4) Uani 1 1 d . . . . .
C24 C 0.08050(9) 0.08743(18) 0.07442(10) 0.0290(4) Uani 1 1 d . . . . .
H24 H 0.037993 0.064132 0.050674 0.035 Uiso 1 1 calc R . . . .
C25 C 0.13349(9) 0.01769(19) 0.05988(11) 0.0327(4) Uani 1 1 d . . . . .
H25 H 0.127375 -0.055051 0.025757 0.039 Uiso 1 1 calc R . . . .
C26 C 0.19607(9) 0.05276(18) 0.09477(11) 0.0320(4) Uani 1 1 d . . . . .
H26 H 0.231653 0.002482 0.084439 0.038 Uiso 1 1 calc R . . . .
C27 C 0.20717(8) 0.15870(18) 0.14379(11) 0.0293(4) Uani 1 1 d . . . . .
H27 H 0.249972 0.181902 0.166439 0.035 Uiso 1 1 calc R . . . .
C28 C 0.15442(8) 0.23192(17) 0.15982(10) 0.0241(4) Uani 1 1 d . . . . .
C29 C 0.14684(8) 0.34449(17) 0.20587(10) 0.0242(4) Uani 1 1 d . . . . .
C30 C 0.08206(8) 0.36807(17) 0.19848(10) 0.0233(4) Uani 1 1 d . . . . .
C31 C 0.05001(8) 0.47480(17) 0.23798(10) 0.0233(4) Uani 1 1 d . . . . .
C32 C 0.02388(8) 0.42025(19) 0.30893(10) 0.0280(4) Uani 1 1 d . . . . .
H32A H 0.059147 0.379454 0.344848 0.042 Uiso 1 1 calc GR . . . .
H32B H -0.009574 0.355546 0.291328 0.042 Uiso 1 1 calc GR . . . .
H32C H 0.005338 0.490856 0.335990 0.042 Uiso 1 1 calc GR . . . .
C33 C -0.00273(8) 0.54121(17) 0.17968(10) 0.0231(4) Uani 1 1 d . . . . .
C34 C -0.06461(8) 0.56165(18) 0.19576(11) 0.0276(4) Uani 1 1 d . . . . .
H34 H -0.075357 0.533767 0.244333 0.033 Uiso 1 1 calc R . . . .
C35 C -0.11080(9) 0.6225(2) 0.14129(12) 0.0350(5) Uani 1 1 d . . . . .
H35 H -0.152896 0.636660 0.153039 0.042 Uiso 1 1 calc R . . . .
C36 C -0.09629(9) 0.66269(19) 0.07046(11) 0.0362(5) Uani 1 1 d . . . . .
H36 H -0.128234 0.703782 0.033217 0.043 Uiso 1 1 calc R . . . .
C37 C -0.03478(9) 0.64277(19) 0.05385(11) 0.0340(5) Uani 1 1 d . . . . .
H37 H -0.024334 0.670325 0.005069 0.041 Uiso 1 1 calc R . . . .
C38 C 0.01146(9) 0.58279(18) 0.10821(10) 0.0290(4) Uani 1 1 d . . . . .
H38 H 0.053630 0.569825 0.096445 0.035 Uiso 1 1 calc R . . . .
C39 C 0.19613(8) 0.42963(18) 0.25397(11) 0.0278(4) Uani 1 1 d . . . . .
H39A H 0.217750 0.484677 0.219198 0.033 Uiso 1 1 calc R . . . .
H39B H 0.229334 0.375562 0.286214 0.033 Uiso 1 1 calc R . . . .
C40 C 0.16228(8) 0.51439(18) 0.30658(11) 0.0286(4) Uani 1 1 d . . . . .
H40 H 0.149620 0.460953 0.349844 0.034 Uiso 1 1 calc R . . . .
C41 C 0.19690(9) 0.6365(2) 0.34004(13) 0.0393(5) Uani 1 1 d . . . . .
H41A H 0.228453 0.666218 0.307179 0.047 Uiso 1 1 calc R . . . .
H41B H 0.219597 0.621919 0.394151 0.047 Uiso 1 1 calc R . . . .
C42 C 0.14136(8) 0.73523(19) 0.33852(12) 0.0328(4) Uani 1 1 d . . . . .
H42 H 0.146449 0.806731 0.300957 0.039 Uiso 1 1 calc R . . . .
C43 C 0.13462(9) 0.79192(18) 0.41685(12) 0.0328(5) Uani 1 1 d . . . . .
C44 C 0.18964(11) 0.9055(2) 0.52467(14) 0.0578(7) Uani 1 1 d . . . . .
H44A H 0.155872 0.971564 0.523174 0.087 Uiso 1 1 calc GR . . . .
H44B H 0.231890 0.944841 0.543208 0.087 Uiso 1 1 calc GR . . . .
H44C H 0.181875 0.835551 0.560308 0.087 Uiso 1 1 calc GR . . . .


_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 N2 1.4791(18) . ?
O1 C20 1.444(2) . ?
O2 C21 1.190(2) . ?
O3 C21 1.335(2) . ?
O3 C22 1.449(2) . ?
O7 H7A 0.8701 . ?
O7 H7B 0.8702 . ?
N1 H1 0.885(14) . ?
N1 C1 1.377(2) . ?
N1 C8 1.378(2) . ?
N2 C9 1.494(2) . ?
N2 C18 1.481(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.412(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(2) . ?
C6 C7 1.431(2) . ?
C7 C8 1.366(2) . ?
C7 C17 1.497(2) . ?
C8 C9 1.505(2) . ?
C9 C10 1.537(2) . ?
C9 C11 1.534(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.390(2) . ?
C11 C16 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.511(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.513(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.519(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.502(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O4 N4 1.4682(19) . ?
O4 C42 1.430(2) . ?
O5 C43 1.202(2) . ?
O6 C43 1.328(2) . ?
O6 C44 1.444(3) . ?
N3 H3A 0.840(19) . ?
N3 C23 1.377(2) . ?
N3 C30 1.371(2) . ?
N4 C31 1.492(2) . ?
N4 C40 1.481(2) . ?
C23 C24 1.390(3) . ?
C23 C28 1.417(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.400(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.379(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.405(2) . ?
C28 C29 1.431(3) . ?
C29 C30 1.367(2) . ?
C29 C39 1.500(2) . ?
C30 C31 1.510(2) . ?
C31 C32 1.532(2) . ?
C31 C33 1.532(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.389(2) . ?
C33 C38 1.387(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.375(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.384(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.382(3) . ?
C38 H38 0.9500 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.520(3) . ?
C40 H40 1.0000 . ?
C40 C41 1.520(3) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C42 1.545(3) . ?
C42 H42 1.0000 . ?
C42 C43 1.504(3) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 N2 105.91(12) . . ?
C21 O3 C22 116.35(15) . . ?
H7A O7 H7B 109.5 . . ?
C1 N1 H1 125.3(12) . . ?
C1 N1 C8 108.55(14) . . ?
C8 N1 H1 125.9(12) . . ?
O1 N2 C9 106.24(12) . . ?
O1 N2 C18 102.81(11) . . ?
C18 N2 C9 113.85(13) . . ?
N1 C1 C2 130.14(16) . . ?
N1 C1 C6 107.66(14) . . ?
C2 C1 C6 122.21(16) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.00(18) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.72(18) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.04(17) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.97(18) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.98(14) . . ?
C5 C6 C1 119.02(16) . . ?
C5 C6 C7 134.00(17) . . ?
C6 C7 C17 130.77(15) . . ?
C8 C7 C6 106.71(15) . . ?
C8 C7 C17 122.47(15) . . ?
N1 C8 C9 122.89(14) . . ?
C7 C8 N1 110.09(14) . . ?
C7 C8 C9 126.97(15) . . ?
N2 C9 C8 102.41(12) . . ?
N2 C9 C10 114.90(13) . . ?
N2 C9 C11 106.47(12) . . ?
C8 C9 C10 108.91(13) . . ?
C8 C9 C11 111.69(13) . . ?
C11 C9 C10 112.09(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 120.53(14) . . ?
C16 C11 C9 121.31(14) . . ?
C16 C11 C12 118.12(15) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.06(16) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.01(17) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.73(16) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.23(16) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.84(16) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C7 C17 H17A 110.2 . . ?
C7 C17 H17B 110.2 . . ?
C7 C17 C18 107.39(14) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
N2 C18 C17 108.06(13) . . ?
N2 C18 H18 109.9 . . ?
N2 C18 C19 100.67(13) . . ?
C17 C18 H18 109.9 . . ?
C17 C18 C19 118.00(15) . . ?
C19 C18 H18 109.9 . . ?
C18 C19 H19A 111.3 . . ?
C18 C19 H19B 111.3 . . ?
C18 C19 C20 102.55(14) . . ?
H19A C19 H19B 109.2 . . ?
C20 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
O1 C20 C19 106.87(14) . . ?
O1 C20 H20 109.0 . . ?
O1 C20 C21 108.00(14) . . ?
C19 C20 H20 109.0 . . ?
C21 C20 C19 114.97(15) . . ?
C21 C20 H20 109.0 . . ?
O2 C21 O3 123.99(19) . . ?
O2 C21 C20 124.63(19) . . ?
O3 C21 C20 111.36(15) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C42 O4 N4 102.58(12) . . ?
C43 O6 C44 115.17(18) . . ?
C23 N3 H3A 124.5(13) . . ?
C30 N3 H3A 126.5(13) . . ?
C30 N3 C23 108.97(14) . . ?
O4 N4 C31 107.10(12) . . ?
O4 N4 C40 101.77(12) . . ?
C40 N4 C31 113.89(14) . . ?
N3 C23 C24 130.05(16) . . ?
N3 C23 C28 107.48(15) . . ?
C24 C23 C28 122.46(16) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 C23 117.76(17) . . ?
C25 C24 H24 121.1 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.90(18) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.44(17) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 120.4 . . ?
C26 C27 C28 119.20(17) . . ?
C28 C27 H27 120.4 . . ?
C23 C28 C29 106.64(15) . . ?
C27 C28 C23 118.23(17) . . ?
C27 C28 C29 135.13(17) . . ?
C28 C29 C39 130.82(15) . . ?
C30 C29 C28 106.97(15) . . ?
C30 C29 C39 122.20(16) . . ?
N3 C30 C31 123.36(14) . . ?
C29 C30 N3 109.93(15) . . ?
C29 C30 C31 126.70(16) . . ?
N4 C31 C30 101.83(13) . . ?
N4 C31 C32 114.33(14) . . ?
N4 C31 C33 107.38(14) . . ?
C30 C31 C32 109.90(15) . . ?
C30 C31 C33 110.78(14) . . ?
C33 C31 C32 112.14(13) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C31 122.31(16) . . ?
C38 C33 C31 119.20(15) . . ?
C38 C33 C34 118.49(16) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.34(18) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.66(17) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.46(17) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 C36 120.00(18) . . ?
C38 C37 H37 120.0 . . ?
C33 C38 H38 119.5 . . ?
C37 C38 C33 121.05(17) . . ?
C37 C38 H38 119.5 . . ?
C29 C39 H39A 109.9 . . ?
C29 C39 H39B 109.9 . . ?
C29 C39 C40 108.72(14) . . ?
H39A C39 H39B 108.3 . . ?
C40 C39 H39A 109.9 . . ?
C40 C39 H39B 109.9 . . ?
N4 C40 C39 107.78(14) . . ?
N4 C40 H40 109.9 . . ?
N4 C40 C41 101.38(14) . . ?
C39 C40 H40 109.9 . . ?
C41 C40 C39 117.57(15) . . ?
C41 C40 H40 109.9 . . ?
C40 C41 H41A 111.1 . . ?
C40 C41 H41B 111.1 . . ?
C40 C41 C42 103.10(14) . . ?
H41A C41 H41B 109.1 . . ?
C42 C41 H41A 111.1 . . ?
C42 C41 H41B 111.1 . . ?
O4 C42 C41 106.05(15) . . ?
O4 C42 H42 109.6 . . ?
O4 C42 C43 106.74(15) . . ?
C41 C42 H42 109.6 . . ?
C43 C42 C41 115.03(16) . . ?
C43 C42 H42 109.6 . . ?
O5 C43 O6 124.92(19) . . ?
O5 C43 C42 125.24(17) . . ?
O6 C43 C42 109.84(17) . . ?
O6 C44 H44A 109.5 . . ?
O6 C44 H44B 109.5 . . ?
O6 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
