# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_V18134
_database_code_depnum_ccdc_archive 'CCDC 1834567'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H51 Cl7 N2 O2 Ti'
_chemical_formula_weight         899.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.3004(7)
_cell_length_b                   15.5000(7)
_cell_length_c                   23.3578(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4453.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      35.88

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.648
_shelx_estimated_absorpt_T_min   0.697
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5519
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.69
_diffrn_reflns_number            76119
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         36.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             21602
_reflns_number_gt                18114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+1.5737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 6901 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.016(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         21602
_refine_ls_number_parameters     541
_refine_ls_number_restraints     217
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.55754(7) 0.68986(4) 0.27486(3) 0.03074(15) Uani 1 1 d . . . . .
Ti1 Ti 0.63071(3) 0.55210(2) 0.28748(2) 0.01503(7) Uani 1 1 d . . . . .
O1 O 0.65617(14) 0.53362(10) 0.21031(7) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.66180(18) 0.47272(14) 0.17012(9) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.6791(2) 0.49514(14) 0.11201(9) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.6835(2) 0.58988(15) 0.09313(10) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.7756(3) 0.6383(2) 0.12367(13) 0.0319(6) Uani 1 1 d . . . . .
H12A H 0.845122 0.610033 0.115386 0.048 Uiso 1 1 calc R U . . .
H12B H 0.762608 0.637744 0.165063 0.048 Uiso 1 1 calc R U . . .
H12C H 0.777960 0.698095 0.110064 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5738(3) 0.63206(18) 0.10668(12) 0.0306(6) Uani 1 1 d . . . . .
H13A H 0.561404 0.630894 0.148114 0.046 Uiso 1 1 calc R U . . .
H13B H 0.515617 0.600283 0.087285 0.046 Uiso 1 1 calc R U . . .
H13C H 0.574305 0.691983 0.093299 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7040(3) 0.59824(19) 0.02836(11) 0.0314(6) Uani 1 1 d . . . . .
H14A H 0.709381 0.659391 0.018079 0.047 Uiso 1 1 calc R U . . .
H14B H 0.643669 0.571766 0.007327 0.047 Uiso 1 1 calc R U . . .
H14C H 0.772002 0.568892 0.018430 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6867(2) 0.42732(15) 0.07326(9) 0.0171(4) Uani 1 1 d . . . . .
H3 H 0.699841 0.441145 0.034240 0.020 Uiso 1 1 calc R U . . .
C4 C 0.67634(18) 0.33954(14) 0.08785(9) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.6857(2) 0.27165(15) 0.04061(9) 0.0170(4) Uani 1 1 d . . . . .
C16 C 0.6785(3) 0.17975(16) 0.06452(11) 0.0241(5) Uani 1 1 d . . . . .
H16A H 0.609374 0.172459 0.084819 0.036 Uiso 1 1 calc R U . . .
H16B H 0.738890 0.169795 0.091081 0.036 Uiso 1 1 calc R U . . .
H16C H 0.682645 0.138217 0.032963 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5931(2) 0.28451(19) -0.00228(11) 0.0240(5) Uani 1 1 d . . . . .
H17A H 0.598410 0.342212 -0.019199 0.036 Uiso 1 1 calc R U . . .
H17B H 0.523169 0.278602 0.017440 0.036 Uiso 1 1 calc R U . . .
H17C H 0.598404 0.240948 -0.032562 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7954(2) 0.28146(18) 0.00983(10) 0.0230(4) Uani 1 1 d . . . . .
H18A H 0.799221 0.240528 -0.022081 0.034 Uiso 1 1 calc R U . . .
H18B H 0.854624 0.269689 0.036813 0.034 Uiso 1 1 calc R U . . .
H18C H 0.802460 0.340426 -0.004854 0.034 Uiso 1 1 calc R U . . .
C5 C 0.65617(19) 0.32004(14) 0.14462(9) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.647143 0.261547 0.155802 0.019 Uiso 1 1 calc R U . . .
C6 C 0.64886(18) 0.38556(14) 0.18602(9) 0.0144(3) Uani 1 1 d . . . . .
C7 C 0.62319(19) 0.36120(13) 0.24416(8) 0.0144(3) Uani 1 1 d . . . . .
H7 H 0.611530 0.301671 0.251624 0.017 Uiso 1 1 calc R U . . .
N1 N 0.61478(15) 0.41402(11) 0.28697(8) 0.0140(3) Uani 1 1 d . . . . .
C8 C 0.58218(18) 0.37935(14) 0.34321(8) 0.0147(3) Uani 1 1 d . . . . .
H8 H 0.543623 0.323035 0.338307 0.018 Uiso 1 1 calc R U . . .
C10 C 0.6821(2) 0.36781(16) 0.38208(9) 0.0199(4) Uani 1 1 d . . . . .
H10A H 0.717525 0.424640 0.387262 0.024 Uiso 1 1 calc R U . . .
H10B H 0.657294 0.347957 0.420185 0.024 Uiso 1 1 calc R U . . .
C41 C 0.7652(2) 0.30489(16) 0.35969(9) 0.0196(4) Uani 1 1 d . . . . .
C42 C 0.7375(2) 0.2210(2) 0.34438(14) 0.0292(5) Uani 1 1 d . . . . .
H42 H 0.663851 0.203033 0.347009 0.035 Uiso 1 1 calc R U . . .
C43 C 0.8160(3) 0.1630(2) 0.32527(14) 0.0358(7) Uani 1 1 d . . . . .
H43 H 0.795254 0.106334 0.314334 0.043 Uiso 1 1 calc R U . . .
C44 C 0.9229(3) 0.1874(3) 0.32215(15) 0.0422(9) Uani 1 1 d . . . . .
H44 H 0.976044 0.148355 0.307920 0.051 Uiso 1 1 calc R U . . .
C45 C 0.9536(3) 0.2706(3) 0.3402(2) 0.0559(12) Uani 1 1 d . . . . .
H45 H 1.028036 0.287010 0.340106 0.067 Uiso 1 1 calc R U . . .
C46 C 0.8744(3) 0.3287(2) 0.35816(18) 0.0391(7) Uani 1 1 d . . . . .
H46 H 0.895042 0.385245 0.369506 0.047 Uiso 1 1 calc R U . . .
C9 C 0.50236(19) 0.44881(14) 0.36664(9) 0.0158(3) Uani 1 1 d . . . . .
C21 C 0.39016(19) 0.44294(15) 0.33797(10) 0.0181(4) Uani 1 1 d . . . . .
C22 C 0.3413(2) 0.36502(16) 0.32313(13) 0.0243(5) Uani 1 1 d . . . . .
H22 H 0.379530 0.312420 0.328754 0.029 Uiso 1 1 calc R U . . .
C23 C 0.2366(3) 0.3637(2) 0.30005(17) 0.0346(7) Uani 1 1 d . . . . .
H23 H 0.204517 0.310288 0.289431 0.041 Uiso 1 1 calc R U . . .
C24 C 0.1794(3) 0.4398(2) 0.29256(18) 0.0386(7) Uani 1 1 d . . . . .
H24 H 0.107354 0.438627 0.277864 0.046 Uiso 1 1 calc R U . . .
C25 C 0.2279(3) 0.5175(2) 0.30669(16) 0.0348(6) Uani 1 1 d . . . . .
H25 H 0.189246 0.569962 0.301294 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3326(2) 0.51945(17) 0.32863(12) 0.0251(5) Uani 1 1 d . . . . .
H26 H 0.365579 0.573267 0.337420 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4871(2) 0.44480(15) 0.43169(9) 0.0180(4) Uani 1 1 d . . . . .
C32 C 0.4418(3) 0.37320(17) 0.45822(11) 0.0291(6) Uani 1 1 d . . . . .
H32 H 0.421111 0.324866 0.435720 0.035 Uiso 1 1 calc R U . . .
C33 C 0.4262(3) 0.37096(19) 0.51727(12) 0.0310(6) Uani 1 1 d . . . . .
H33 H 0.396369 0.321038 0.534862 0.037 Uiso 1 1 calc R U . . .
C34 C 0.4545(3) 0.4421(2) 0.55037(10) 0.0274(5) Uani 1 1 d . . . . .
H34 H 0.443714 0.441168 0.590635 0.033 Uiso 1 1 calc R U . . .
C35 C 0.4984(3) 0.51414(19) 0.52418(10) 0.0272(5) Uani 1 1 d . . . . .
H35 H 0.516971 0.563159 0.546565 0.033 Uiso 1 1 calc R U . . .
C36 C 0.5158(2) 0.51537(17) 0.46521(10) 0.0219(4) Uani 1 1 d . . . . .
H36 H 0.547342 0.564762 0.447804 0.026 Uiso 1 1 calc R U . . .
O2 O 0.55040(15) 0.52858(10) 0.35220(7) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.77078(19) 0.57126(16) 0.31538(9) 0.0237(4) Uani 1 1 d . . . . .
C51 C 0.7901(3) 0.6033(2) 0.37306(12) 0.0359(7) Uani 1 1 d . . . . .
H51A H 0.844828 0.567261 0.391926 0.054 Uiso 1 1 calc R U . . .
H51B H 0.722166 0.601377 0.394954 0.054 Uiso 1 1 calc R U . . .
H51C H 0.816255 0.662988 0.371130 0.054 Uiso 1 1 calc R U . . .
C52 C 0.8701(3) 0.5682(3) 0.28187(14) 0.0420(8) Uani 1 1 d . . . . .
H52A H 0.899703 0.626592 0.277917 0.063 Uiso 1 1 calc R U . . .
H52B H 0.854244 0.544594 0.243855 0.063 Uiso 1 1 calc R U . . .
H52C H 0.923392 0.531338 0.301220 0.063 Uiso 1 1 calc R U . . .
C1S C 0.1738(4) 0.4465(3) 0.4577(3) 0.0552(11) Uani 1 1 d D . . . .
H1S1 H 0.213917 0.445231 0.420949 0.066 Uiso 1 1 calc R U . . .
H1S2 H 0.225025 0.465312 0.487933 0.066 Uiso 1 1 calc R U . . .
Cl1S Cl 0.12688(11) 0.34248(7) 0.47359(6) 0.0552(3) Uani 1 1 d D . . . .
Cl2S Cl 0.06698(12) 0.52092(9) 0.45279(11) 0.1012(8) Uani 1 1 d D . . . .
C2S C -0.0815(6) 0.3314(6) 0.1786(5) 0.0509(19) Uani 0.519(3) 1 d D U P A 1
H2S1 H -0.161793 0.332005 0.181373 0.061 Uiso 0.519(3) 1 calc R U P A 1
H2S2 H -0.056126 0.325505 0.218634 0.061 Uiso 0.519(3) 1 calc R U P A 1
Cl3S Cl -0.0580(7) 0.2317(4) 0.1525(4) 0.0604(17) Uani 0.519(3) 1 d D U P A 1
Cl4S Cl -0.05872(14) 0.41774(10) 0.16733(6) 0.0339(4) Uani 0.519(3) 1 d D U P A
1
C2T C -0.0565(9) 0.3189(5) 0.2025(3) 0.048(2) Uani 0.481(3) 1 d D U P A 2
H2T1 H -0.032036 0.301088 0.241144 0.057 Uiso 0.481(3) 1 calc R U P A 2
H2T2 H -0.127915 0.347839 0.206021 0.057 Uiso 0.481(3) 1 calc R U P A 2
Cl3T Cl -0.0658(6) 0.2283(3) 0.1565(3) 0.0401(10) Uani 0.481(3) 1 d D U P A 2
Cl4T Cl 0.0426(2) 0.3909(3) 0.16974(13) 0.0818(12) Uani 0.481(3) 1 d D U P A 2
C3S C 0.3632(9) 0.3901(7) 0.1420(5) 0.071(4) Uani 0.519(3) 1 d D U P A 1
H3S1 H 0.394496 0.337121 0.159074 0.085 Uiso 0.519(3) 1 calc R U P A 1
H3S2 H 0.402377 0.401240 0.105732 0.085 Uiso 0.519(3) 1 calc R U P A 1
Cl5S Cl 0.3874(3) 0.4768(3) 0.18889(10) 0.0505(9) Uani 0.519(3) 1 d D U P A 1
Cl6S Cl 0.2210(3) 0.3699(3) 0.1255(2) 0.124(2) Uani 0.519(3) 1 d D U P A 1
C3T C 0.3908(9) 0.4131(13) 0.1259(8) 0.103(7) Uani 0.481(3) 1 d D U P A 2
H3T1 H 0.392646 0.353708 0.141464 0.123 Uiso 0.481(3) 1 calc R U P A 2
H3T2 H 0.456133 0.421779 0.101810 0.123 Uiso 0.481(3) 1 calc R U P A 2
Cl5T Cl 0.3888(4) 0.4838(3) 0.1784(3) 0.0877(18) Uani 0.481(3) 1 d D U P A 2
Cl6T Cl 0.27781(19) 0.42761(18) 0.08669(9) 0.0519(6) Uani 0.481(3) 1 d D U P A
2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Ti1 2.3358(8) . ?
Ti1 O2 1.8424(16) . ?
Ti1 O1 1.8518(17) . ?
Ti1 N2 1.866(2) . ?
Ti1 N1 2.1492(18) . ?
O1 C1 1.333(3) . ?
C1 C6 1.410(3) . ?
C1 C2 1.417(3) . ?
C2 C3 1.390(3) . ?
C2 C11 1.534(3) . ?
C11 C13 1.532(5) . ?
C11 C12 1.535(4) . ?
C11 C14 1.539(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 C4 1.409(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 C15 1.529(3) . ?
C15 C17 1.530(4) . ?
C15 C16 1.533(3) . ?
C15 C18 1.537(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(3) . ?
C7 N1 1.297(3) . ?
C7 H7 0.9500 . ?
N1 C8 1.475(3) . ?
C8 C10 1.539(3) . ?
C8 C9 1.556(3) . ?
C8 H8 1.0000 . ?
C10 C41 1.506(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C41 C42 1.390(4) . ?
C41 C46 1.394(4) . ?
C42 C43 1.393(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.371(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.409(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.391(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C9 O2 1.411(3) . ?
C9 C31 1.532(3) . ?
C9 C21 1.537(3) . ?
C21 C22 1.393(4) . ?
C21 C26 1.398(3) . ?
C22 C23 1.396(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.388(3) . ?
C31 C36 1.391(3) . ?
C32 C33 1.393(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N2 C52 1.452(4) . ?
N2 C51 1.456(3) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C1S Cl1S 1.752(5) . ?
C1S Cl2S 1.753(4) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2S Cl4S 1.393(9) . ?
C2S Cl3S 1.686(10) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?
C2T Cl3T 1.772(9) . ?
C2T Cl4T 1.821(9) . ?
C2T H2T1 0.9900 . ?
C2T H2T2 0.9900 . ?
C3S Cl5S 1.759(9) . ?
C3S Cl6S 1.818(11) . ?
C3S H3S1 0.9900 . ?
C3S H3S2 0.9900 . ?
C3T Cl5T 1.646(13) . ?
C3T Cl6T 1.679(13) . ?
C3T H3T1 0.9900 . ?
C3T H3T2 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
O2 Ti1 O1 149.18(8) . . ?
O2 Ti1 N2 103.88(9) . . ?
O1 Ti1 N2 102.03(9) . . ?
O2 Ti1 N1 76.03(7) . . ?
O1 Ti1 N1 81.72(7) . . ?
N2 Ti1 N1 104.15(9) . . ?
O2 Ti1 Cl1 94.47(6) . . ?
O1 Ti1 Cl1 94.81(6) . . ?
N2 Ti1 Cl1 104.74(8) . . ?
N1 Ti1 Cl1 150.99(6) . . ?
C1 O1 Ti1 143.50(14) . . ?
O1 C1 C6 119.14(18) . . ?
O1 C1 C2 120.58(19) . . ?
C6 C1 C2 120.28(19) . . ?
C3 C2 C1 116.63(19) . . ?
C3 C2 C11 122.29(19) . . ?
C1 C2 C11 121.02(19) . . ?
C13 C11 C2 108.5(2) . . ?
C13 C11 C12 110.2(2) . . ?
C2 C11 C12 111.1(2) . . ?
C13 C11 C14 108.1(2) . . ?
C2 C11 C14 111.6(2) . . ?
C12 C11 C14 107.1(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 C4 124.52(19) . . ?
C2 C3 H3 117.7 . . ?
C4 C3 H3 117.7 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C15 123.73(19) . . ?
C3 C4 C15 118.90(19) . . ?
C4 C15 C17 109.1(2) . . ?
C4 C15 C16 111.85(18) . . ?
C17 C15 C16 108.5(2) . . ?
C4 C15 C18 109.60(19) . . ?
C17 C15 C18 109.55(19) . . ?
C16 C15 C18 108.2(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.26(18) . . ?
C5 C6 C7 118.16(19) . . ?
C1 C6 C7 121.52(18) . . ?
N1 C7 C6 125.28(19) . . ?
N1 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
C7 N1 C8 118.60(18) . . ?
C7 N1 Ti1 128.74(15) . . ?
C8 N1 Ti1 112.50(13) . . ?
N1 C8 C10 110.52(18) . . ?
N1 C8 C9 103.45(16) . . ?
C10 C8 C9 112.14(17) . . ?
N1 C8 H8 110.2 . . ?
C10 C8 H8 110.2 . . ?
C9 C8 H8 110.2 . . ?
C41 C10 C8 114.36(19) . . ?
C41 C10 H10A 108.7 . . ?
C8 C10 H10A 108.7 . . ?
C41 C10 H10B 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C42 C41 C46 118.5(3) . . ?
C42 C41 C10 121.9(2) . . ?
C46 C41 C10 119.4(3) . . ?
C41 C42 C43 121.1(3) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 120.3(3) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.5(3) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 119.7(4) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C41 120.7(4) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?
O2 C9 C31 108.89(18) . . ?
O2 C9 C21 108.90(18) . . ?
C31 C9 C21 108.65(18) . . ?
O2 C9 C8 104.95(17) . . ?
C31 C9 C8 113.44(18) . . ?
C21 C9 C8 111.86(17) . . ?
C22 C21 C26 118.6(2) . . ?
C22 C21 C9 123.2(2) . . ?
C26 C21 C9 118.2(2) . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C32 C31 C36 118.6(2) . . ?
C32 C31 C9 121.6(2) . . ?
C36 C31 C9 119.7(2) . . ?
C31 C32 C33 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 119.8(3) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 119.5(2) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C34 C35 C36 120.5(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 120.5(2) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C9 O2 Ti1 126.43(13) . . ?
C52 N2 C51 111.9(2) . . ?
C52 N2 Ti1 125.70(18) . . ?
C51 N2 Ti1 121.9(2) . . ?
N2 C51 H51A 109.5 . . ?
N2 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N2 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N2 C52 H52A 109.5 . . ?
N2 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
N2 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
Cl1S C1S Cl2S 111.8(2) . . ?
Cl1S C1S H1S1 109.2 . . ?
Cl2S C1S H1S1 109.2 . . ?
Cl1S C1S H1S2 109.2 . . ?
Cl2S C1S H1S2 109.2 . . ?
H1S1 C1S H1S2 107.9 . . ?
Cl4S C2S Cl3S 141.1(7) . . ?
Cl4S C2S H2S1 101.7 . . ?
Cl3S C2S H2S1 101.7 . . ?
Cl4S C2S H2S2 101.7 . . ?
Cl3S C2S H2S2 101.7 . . ?
H2S1 C2S H2S2 104.7 . . ?
Cl3T C2T Cl4T 105.9(5) . . ?
Cl3T C2T H2T1 110.6 . . ?
Cl4T C2T H2T1 110.6 . . ?
Cl3T C2T H2T2 110.6 . . ?
Cl4T C2T H2T2 110.6 . . ?
H2T1 C2T H2T2 108.7 . . ?
Cl5S C3S Cl6S 115.2(5) . . ?
Cl5S C3S H3S1 108.5 . . ?
Cl6S C3S H3S1 108.5 . . ?
Cl5S C3S H3S2 108.5 . . ?
Cl6S C3S H3S2 108.5 . . ?
H3S1 C3S H3S2 107.5 . . ?
Cl5T C3T Cl6T 107.8(8) . . ?
Cl5T C3T H3T1 110.2 . . ?
Cl6T C3T H3T1 110.2 . . ?
Cl5T C3T H3T2 110.2 . . ?
Cl6T C3T H3T2 110.2 . . ?
H3T1 C3T H3T2 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ti1 O1 C1 -42.5(3) . . . . ?
N2 Ti1 O1 C1 104.2(3) . . . . ?
N1 Ti1 O1 C1 1.4(3) . . . . ?
Cl1 Ti1 O1 C1 -149.6(3) . . . . ?
Ti1 O1 C1 C6 -3.3(4) . . . . ?
Ti1 O1 C1 C2 175.88(19) . . . . ?
O1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C3 -2.5(3) . . . . ?
O1 C1 C2 C11 -4.5(3) . . . . ?
C6 C1 C2 C11 174.7(2) . . . . ?
C3 C2 C11 C13 115.6(3) . . . . ?
C1 C2 C11 C13 -61.4(3) . . . . ?
C3 C2 C11 C12 -123.0(3) . . . . ?
C1 C2 C11 C12 59.9(3) . . . . ?
C3 C2 C11 C14 -3.5(4) . . . . ?
C1 C2 C11 C14 179.5(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C11 C2 C3 C4 -175.8(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C15 179.5(2) . . . . ?
C5 C4 C15 C17 115.8(3) . . . . ?
C3 C4 C15 C17 -63.0(3) . . . . ?
C5 C4 C15 C16 -4.3(3) . . . . ?
C3 C4 C15 C16 176.9(2) . . . . ?
C5 C4 C15 C18 -124.3(2) . . . . ?
C3 C4 C15 C18 56.9(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C15 C4 C5 C6 179.8(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
O1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
O1 C1 C6 C7 3.8(3) . . . . ?
C2 C1 C6 C7 -175.4(2) . . . . ?
C5 C6 C7 N1 179.3(2) . . . . ?
C1 C6 C7 N1 -3.4(4) . . . . ?
C6 C7 N1 C8 176.7(2) . . . . ?
C6 C7 N1 Ti1 1.8(3) . . . . ?
C7 N1 C8 C10 100.5(2) . . . . ?
Ti1 N1 C8 C10 -83.73(18) . . . . ?
C7 N1 C8 C9 -139.3(2) . . . . ?
Ti1 N1 C8 C9 36.49(19) . . . . ?
N1 C8 C10 C41 -61.9(3) . . . . ?
C9 C8 C10 C41 -176.73(19) . . . . ?
C8 C10 C41 C42 -53.8(3) . . . . ?
C8 C10 C41 C46 131.1(3) . . . . ?
C46 C41 C42 C43 -3.1(4) . . . . ?
C10 C41 C42 C43 -178.2(3) . . . . ?
C41 C42 C43 C44 1.2(5) . . . . ?
C42 C43 C44 C45 2.1(6) . . . . ?
C43 C44 C45 C46 -3.3(7) . . . . ?
C44 C45 C46 C41 1.4(7) . . . . ?
C42 C41 C46 C45 1.8(5) . . . . ?
C10 C41 C46 C45 177.0(3) . . . . ?
N1 C8 C9 O2 -41.3(2) . . . . ?
C10 C8 C9 O2 77.8(2) . . . . ?
N1 C8 C9 C31 -160.05(18) . . . . ?
C10 C8 C9 C31 -40.9(3) . . . . ?
N1 C8 C9 C21 76.6(2) . . . . ?
C10 C8 C9 C21 -164.27(18) . . . . ?
O2 C9 C21 C22 152.7(2) . . . . ?
C31 C9 C21 C22 -88.8(3) . . . . ?
C8 C9 C21 C22 37.2(3) . . . . ?
O2 C9 C21 C26 -30.1(3) . . . . ?
C31 C9 C21 C26 88.4(3) . . . . ?
C8 C9 C21 C26 -145.7(2) . . . . ?
C26 C21 C22 C23 -0.7(4) . . . . ?
C9 C21 C22 C23 176.5(3) . . . . ?
C21 C22 C23 C24 -1.1(5) . . . . ?
C22 C23 C24 C25 1.8(6) . . . . ?
C23 C24 C25 C26 -0.6(6) . . . . ?
C24 C25 C26 C21 -1.3(5) . . . . ?
C22 C21 C26 C25 1.9(4) . . . . ?
C9 C21 C26 C25 -175.4(3) . . . . ?
O2 C9 C31 C32 -179.7(3) . . . . ?
C21 C9 C31 C32 61.8(3) . . . . ?
C8 C9 C31 C32 -63.3(3) . . . . ?
O2 C9 C31 C36 2.4(3) . . . . ?
C21 C9 C31 C36 -116.0(2) . . . . ?
C8 C9 C31 C36 118.9(2) . . . . ?
C36 C31 C32 C33 -0.8(5) . . . . ?
C9 C31 C32 C33 -178.6(3) . . . . ?
C31 C32 C33 C34 1.2(5) . . . . ?
C32 C33 C34 C35 -0.4(5) . . . . ?
C33 C34 C35 C36 -0.8(5) . . . . ?
C32 C31 C36 C35 -0.5(4) . . . . ?
C9 C31 C36 C35 177.5(3) . . . . ?
C34 C35 C36 C31 1.3(5) . . . . ?
C31 C9 O2 Ti1 155.95(16) . . . . ?
C21 C9 O2 Ti1 -85.7(2) . . . . ?
C8 C9 O2 Ti1 34.2(2) . . . . ?
O1 Ti1 O2 C9 33.9(3) . . . . ?
N2 Ti1 O2 C9 -112.59(19) . . . . ?
N1 Ti1 O2 C9 -11.17(18) . . . . ?
Cl1 Ti1 O2 C9 141.02(18) . . . . ?
O2 Ti1 N2 C52 161.4(3) . . . . ?
O1 Ti1 N2 C52 -1.8(3) . . . . ?
N1 Ti1 N2 C52 82.6(3) . . . . ?
Cl1 Ti1 N2 C52 -100.1(3) . . . . ?
O2 Ti1 N2 C51 -27.5(3) . . . . ?
O1 Ti1 N2 C51 169.3(2) . . . . ?
N1 Ti1 N2 C51 -106.3(3) . . . . ?
Cl1 Ti1 N2 C51 71.0(3) . . . . ?

_refine_diff_density_max         1.209
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_hm_1
_database_code_depnum_ccdc_archive 'CCDC 1837506'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.03.02 svn.r3394 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H21 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.27660(10)
_cell_length_b                   13.5578(2)
_cell_length_c                   17.4247(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1482.79(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1500
_cell_measurement_theta_min      4.0720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33b (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 9 2 0.1224
1 8 -1 0.1263
3 4 -5 0.0971
1 -8 -3 0.1695
-3 -6 4 0.1268
-3 -2 6 0.1226
-3 5 6 0.1444
2 7 1 0.1288
0 3 -10 0.0493
-3 -5 -5 0.1666
0 -4 10 0.0838
3 5 1 0.1225
-4 -1 -5 0.1504
-3 -6 0 0.1510
1 -6 7 0.0971
2 -1 5 0.1141
1 8 -3 0.1247
-1 8 -3 0.1142
-4 3 -2 0.1280
-3 -6 2 0.1373
1 -8 3 0.1387
3 -6 3 0.1610
0 2 5 0.1395

_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.144
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3117 8.6426 1.9071 0.5244 -0.4016 0.7508
1.2265 8.3550 -0.8900 0.2084 -0.1590 0.9650
3.1650 3.8995 -5.0537 -0.4093 0.3149 0.8563
0.9519 -8.2312 -2.9883 -0.6274 0.4808 -0.6125
-2.7479 -5.6833 4.0290 0.2322 -0.1790 -0.9561
-3.3479 -2.4772 5.6032 0.5214 -0.4007 -0.7534
-2.7542 4.7581 5.6705 0.7933 -0.6087 0.0090
2.4555 6.9196 1.4515 0.2737 0.2346 0.9328
-0.4809 3.2686 -10.4237 -0.6775 -0.5782 0.4546
-2.5511 -5.4154 -5.3976 -0.5237 -0.4480 -0.7246
0.2410 -3.8787 10.1376 0.6419 0.5477 -0.5366
3.2049 5.3164 1.3696 0.1624 0.4605 0.8727
-3.5544 -1.4808 -5.1901 -0.2934 -0.8295 -0.4752
-2.9411 -6.0750 -0.2624 -0.1184 -0.3363 -0.9343
0.9733 -6.4890 7.1535 0.2571 0.7249 -0.6391
1.9999 -1.0012 4.9957 0.2563 0.6165 0.0521
1.4850 7.9003 -2.7630 0.0260 -0.1438 0.9893
-1.1479 8.0604 -3.2343 0.1311 -0.7096 0.6923
-3.7365 3.2282 -1.8065 0.1812 -0.9770 -0.1129
-2.8116 -6.1838 1.9054 0.0444 -0.2362 -0.9707
0.8338 -8.2335 3.2509 -0.1206 0.6533 -0.7475
2.6921 -6.2460 2.7875 -0.1724 0.9310 -0.3218
0.0005 1.9969 4.9991 0.4833 0.0659 0.0944

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13819
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.550
_diffrn_reflns_theta_max         66.550
_diffrn_reflns_theta_min         6.038
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     98.00 178.00   0.50    0.20    --  105.75  37.00-120.00  160
  2  ω    -56.00  24.00   0.50    0.10    --  -48.91  37.00-120.00  160
  3  ω    -58.00 -11.00   0.50    0.20    --  -84.25  19.00-180.00   94
  4  ω    -58.00 -11.00   0.50    0.20    --  -84.25  19.00-120.00   94
  5  ω   -120.00 -41.00   0.50    0.10    --  -48.91 -37.00 -30.00  158
  6  ω   -155.00-102.00   0.50    0.20    --  -84.25 -57.00-180.00  106
  7  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00-120.00   64
  8  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00-150.00   64
  9  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00 -90.00   64
 10  ω     35.00 119.00   0.50    0.20    --  105.75 -57.00-150.00  168
 11  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00 -60.00   64
 12  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00-180.00   64
 13  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00   0.00   64
 14  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00  30.00   64
 15  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00 120.00   64
 16  ω     33.00  65.00   0.50    0.20    --  105.75 -37.00 150.00   64
 17  ω   -120.00 -28.00   0.50    0.10    --  -48.91 -77.00 150.00  184
 18  ω   -120.00 -36.00   0.50    0.10    --  -48.91 -57.00  60.00  168
 19  ω   -120.00 -36.00   0.50    0.10    --  -48.91 -57.00 -60.00  168
 20  ω   -120.00 -26.00   0.50    0.10    --  -48.91 -82.00-136.00  188
 21  ω     34.00 110.00   0.50    0.20    --  105.75 -99.00-120.00  152
 22  ω     31.00  94.00   0.50    0.10    --   48.91-125.00  60.00  126
 23  ω     34.00 110.00   0.50    0.20    --  105.75 -99.00 120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0517900000
_diffrn_orient_matrix_UB_12      0.0410948000
_diffrn_orient_matrix_UB_13      0.0802696000
_diffrn_orient_matrix_UB_21      0.2064903000
_diffrn_orient_matrix_UB_22      -0.0459822000
_diffrn_orient_matrix_UB_23      0.0315297000
_diffrn_orient_matrix_UB_31      0.1220684000
_diffrn_orient_matrix_UB_32      0.0955295000
_diffrn_orient_matrix_UB_33      -0.0192874000
_diffrn_oxdiff_ac3_digest_frames 
;
0117adae6b3b44044f9b9e5b36e9a2eb7c02654131b
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01248de56741bfee58a3b66911521ceb3e0980
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2596
_reflns_number_total             2621
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      0.903
_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+0.3856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0587
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.02056(18) 0.40023(8) 0.61737(6) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.63932(18) 0.46681(8) 0.69710(6) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.3528(2) 0.46243(9) 0.57960(7) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.3359(3) 0.19286(12) 0.57752(8) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.2632(3) 0.29115(11) 0.58549(9) 0.0150(3) Uani 1 1 d . . . . .
C13 C 0.3634(3) 0.62674(11) 0.45981(8) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.0497(2) 0.31078(11) 0.61163(8) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.5062(2) 0.54332(11) 0.58054(9) 0.0145(3) Uani 1 1 d . . . . .
C7 C 0.4068(2) 0.37018(11) 0.57225(8) 0.0145(3) Uani 1 1 d . . . . .
C14 C 0.5280(3) 0.64172(11) 0.40746(9) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.2069(3) 0.11495(12) 0.59572(9) 0.0191(3) Uani 1 1 d . . . . .
C18 C 0.1615(3) 0.60397(11) 0.43179(9) 0.0179(3) Uani 1 1 d . . . . .
C15 C 0.4918(3) 0.63451(11) 0.32887(9) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.7911(3) 0.62344(12) 0.66048(10) 0.0204(4) Uani 1 1 d . . . . .
C2 C -0.0763(3) 0.22774(12) 0.63140(9) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.4037(3) 0.63532(11) 0.54506(9) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.1241(3) 0.59718(11) 0.35307(9) 0.0195(4) Uani 1 1 d . . . . .
C3 C -0.0006(3) 0.13332(12) 0.62326(9) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.4233(3) 0.60790(13) 0.71544(9) 0.0200(4) Uani 1 1 d . . . . .
C16 C 0.2899(3) 0.61312(12) 0.30184(9) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.5904(2) 0.56018(11) 0.66411(9) 0.0156(3) Uani 1 1 d . . . . .
H2A H -0.220(3) 0.2398(13) 0.6510(10) 0.017(4) Uiso 1 1 d . . . . .
H5 H 0.480(3) 0.1801(13) 0.5605(10) 0.017(4) Uiso 1 1 d . . . . .
H12A H 0.493(3) 0.6915(15) 0.5552(11) 0.021(5) Uiso 1 1 d . . . . .
H11A H 0.394(3) 0.6771(14) 0.6991(11) 0.022(5) Uiso 1 1 d . . . . .
H14 H 0.673(3) 0.6572(12) 0.4272(10) 0.013(4) Uiso 1 1 d . . . . .
H16 H 0.266(3) 0.6089(14) 0.2475(12) 0.029(5) Uiso 1 1 d . . . . .
H11B H 0.290(3) 0.5717(14) 0.7135(11) 0.024(5) Uiso 1 1 d . . . . .
H8 H 0.629(3) 0.5230(13) 0.5490(10) 0.014(4) Uiso 1 1 d . . . . .
H15 H 0.609(4) 0.6461(15) 0.2931(12) 0.028(5) Uiso 1 1 d . . . . .
H10A H 0.901(4) 0.5892(15) 0.6288(12) 0.029(5) Uiso 1 1 d . . . . .
H12B H 0.260(3) 0.6487(14) 0.5719(11) 0.023(5) Uiso 1 1 d . . . . .
H17 H -0.020(3) 0.5815(13) 0.3331(11) 0.021(5) Uiso 1 1 d . . . . .
H4 H 0.260(3) 0.0485(15) 0.5911(11) 0.023(5) Uiso 1 1 d . . . . .
H10B H 0.765(3) 0.6869(16) 0.6376(12) 0.029(5) Uiso 1 1 d . . . . .
H10C H 0.849(3) 0.6313(15) 0.7140(12) 0.031(5) Uiso 1 1 d . . . . .
H11C H 0.480(4) 0.6087(15) 0.7702(12) 0.036(6) Uiso 1 1 d . . . . .
H18 H 0.043(3) 0.5913(14) 0.4683(11) 0.024(5) Uiso 1 1 d . . . . .
H3 H -0.094(4) 0.0776(15) 0.6366(11) 0.029(5) Uiso 1 1 d . . . . .
H7 H 0.556(3) 0.3565(12) 0.5580(9) 0.009(4) Uiso 1 1 d . . . . .
H2 H 0.753(4) 0.4425(18) 0.6721(13) 0.042(6) Uiso 1 1 d . . . . .
H1 H 0.210(3) 0.4698(14) 0.5935(11) 0.022(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2942(19) . ?
O2 C9 1.4237(18) . ?
O2 H2 0.90(3) . ?
N1 C8 1.4593(19) . ?
N1 C7 1.302(2) . ?
N1 H1 0.94(2) . ?
C5 C6 1.416(2) . ?
C5 C4 1.368(2) . ?
C5 H5 0.970(19) . ?
C6 C1 1.440(2) . ?
C6 C7 1.419(2) . ?
C13 C14 1.393(2) . ?
C13 C18 1.392(2) . ?
C13 C12 1.511(2) . ?
C1 C2 1.418(2) . ?
C8 C12 1.534(2) . ?
C8 C9 1.566(2) . ?
C8 H8 0.988(19) . ?
C7 H7 0.986(18) . ?
C14 C15 1.391(2) . ?
C14 H14 0.998(19) . ?
C4 C3 1.410(2) . ?
C4 H4 0.96(2) . ?
C18 C17 1.395(2) . ?
C18 H18 0.99(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.98(2) . ?
C10 C9 1.525(2) . ?
C10 H10A 1.00(2) . ?
C10 H10B 0.96(2) . ?
C10 H10C 1.01(2) . ?
C2 C3 1.373(2) . ?
C2 H2A 0.979(19) . ?
C12 H12A 0.96(2) . ?
C12 H12B 1.03(2) . ?
C17 C16 1.388(2) . ?
C17 H17 0.99(2) . ?
C3 H3 0.98(2) . ?
C11 C9 1.523(2) . ?
C11 H11A 0.998(19) . ?
C11 H11B 0.97(2) . ?
C11 H11C 1.02(2) . ?
C16 H16 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 107.6(15) . . ?
C8 N1 H1 123.4(12) . . ?
C7 N1 C8 123.45(13) . . ?
C7 N1 H1 112.2(12) . . ?
C6 C5 H5 120.0(11) . . ?
C4 C5 C6 120.87(15) . . ?
C4 C5 H5 119.1(11) . . ?
C5 C6 C1 120.34(14) . . ?
C5 C6 C7 119.33(14) . . ?
C7 C6 C1 120.20(13) . . ?
C14 C13 C12 120.54(14) . . ?
C18 C13 C14 118.53(14) . . ?
C18 C13 C12 120.94(14) . . ?
O1 C1 C6 120.96(14) . . ?
O1 C1 C2 122.36(14) . . ?
C2 C1 C6 116.67(14) . . ?
N1 C8 C12 109.27(13) . . ?
N1 C8 C9 110.05(12) . . ?
N1 C8 H8 107.5(10) . . ?
C12 C8 C9 113.44(12) . . ?
C12 C8 H8 109.4(10) . . ?
C9 C8 H8 107.0(10) . . ?
N1 C7 C6 122.95(14) . . ?
N1 C7 H7 116.9(10) . . ?
C6 C7 H7 120.1(10) . . ?
C13 C14 H14 118.9(10) . . ?
C15 C14 C13 120.86(15) . . ?
C15 C14 H14 120.2(10) . . ?
C5 C4 C3 119.29(15) . . ?
C5 C4 H4 119.9(12) . . ?
C3 C4 H4 120.8(12) . . ?
C13 C18 H18 119.5(11) . . ?
C17 C18 C13 120.86(15) . . ?
C17 C18 H18 119.6(12) . . ?
C14 C15 H15 119.5(12) . . ?
C16 C15 C14 119.97(15) . . ?
C16 C15 H15 120.6(12) . . ?
C9 C10 H10A 109.4(12) . . ?
C9 C10 H10B 112.2(13) . . ?
C9 C10 H10C 108.7(12) . . ?
H10A C10 H10B 107.8(18) . . ?
H10A C10 H10C 108.2(17) . . ?
H10B C10 H10C 110.6(17) . . ?
C1 C2 H2A 117.8(11) . . ?
C3 C2 C1 121.48(15) . . ?
C3 C2 H2A 120.7(11) . . ?
C13 C12 C8 113.82(13) . . ?
C13 C12 H12A 109.8(11) . . ?
C13 C12 H12B 108.3(11) . . ?
C8 C12 H12A 108.9(12) . . ?
C8 C12 H12B 109.1(11) . . ?
H12A C12 H12B 106.8(15) . . ?
C18 C17 H17 120.9(11) . . ?
C16 C17 C18 119.72(16) . . ?
C16 C17 H17 119.4(11) . . ?
C4 C3 H3 119.6(12) . . ?
C2 C3 C4 121.30(15) . . ?
C2 C3 H3 119.1(12) . . ?
C9 C11 H11A 110.9(11) . . ?
C9 C11 H11B 111.0(11) . . ?
C9 C11 H11C 108.3(13) . . ?
H11A C11 H11B 108.0(17) . . ?
H11A C11 H11C 108.7(15) . . ?
H11B C11 H11C 109.8(17) . . ?
C15 C16 C17 120.06(15) . . ?
C15 C16 H16 119.5(13) . . ?
C17 C16 H16 120.5(13) . . ?
O2 C9 C8 108.57(11) . . ?
O2 C9 C10 109.79(13) . . ?
O2 C9 C11 106.82(12) . . ?
C10 C9 C8 108.80(12) . . ?
C11 C9 C8 112.06(13) . . ?
C11 C9 C10 110.75(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.51(15) . . . . ?
N1 C8 C12 C13 -68.78(17) . . . . ?
N1 C8 C9 O2 44.93(16) . . . . ?
N1 C8 C9 C10 164.38(13) . . . . ?
N1 C8 C9 C11 -72.82(16) . . . . ?
C5 C6 C1 O1 -178.29(14) . . . . ?
C5 C6 C1 C2 2.5(2) . . . . ?
C5 C6 C7 N1 -178.89(14) . . . . ?
C5 C4 C3 C2 0.7(2) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C13 C18 C17 C16 0.1(2) . . . . ?
C1 C6 C7 N1 -2.9(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C8 N1 C7 C6 167.97(13) . . . . ?
C7 N1 C8 C12 148.13(13) . . . . ?
C7 N1 C8 C9 -86.69(17) . . . . ?
C7 C6 C1 O1 5.8(2) . . . . ?
C7 C6 C1 C2 -173.41(14) . . . . ?
C14 C13 C18 C17 -0.6(2) . . . . ?
C14 C13 C12 C8 -80.22(18) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C4 C5 C6 C1 -1.2(2) . . . . ?
C4 C5 C6 C7 174.76(13) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
C18 C13 C12 C8 99.91(17) . . . . ?
C18 C17 C16 C15 0.7(2) . . . . ?
C12 C13 C14 C15 -179.62(14) . . . . ?
C12 C13 C18 C17 179.27(14) . . . . ?
C12 C8 C9 O2 167.68(12) . . . . ?
C12 C8 C9 C10 -72.87(16) . . . . ?
C12 C8 C9 C11 49.94(17) . . . . ?
C9 C8 C12 C13 168.04(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.501
_oxdiff_exptl_absorpt_empirical_full_min 0.842
####################################################################### 
# 
# 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_er_proc
_database_code_depnum_ccdc_archive 'CCDC 1837509'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.03.02 svn.r3394 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 F N O2'
_chemical_formula_sum            'C24 H24 F N O2'
_chemical_formula_weight         377.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H23 F O2 N '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.12710(10)
_cell_length_b                   16.0917(3)
_cell_length_c                   19.7246(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1944.76(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10789
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.9570
_cell_measurement_theta_min      3.5120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.4a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'yellowish orange'
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.083
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         5.940
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 120.00   0.50    0.57    --   47.45  57.00 -90.00  174
  2  ω     95.00 178.00   0.50    2.28    --  107.75  19.00 -30.00  166
  3  ω     85.00 120.00   0.50    0.57    --   47.45  77.00 120.00   70
  4  ω     33.00 120.00   0.50    0.57    --   47.45  57.00 120.00  174
  5  ω     35.00  82.00   0.50    2.28    --  107.75 -57.00   0.00   94
  6  ω     35.00 117.00   0.50    2.28    --  107.75-125.00   0.00  164
  7  ω     35.00  62.00   0.50    2.28    --  107.75 -37.00 120.00   54
  8  ω     35.00  62.00   0.50    2.28    --  107.75 -37.00 150.00   54
  9  ω     35.00 121.00   0.50    0.57    --   47.45  37.00-120.00  172
 10  ω     35.00  62.00   0.50    2.28    --  107.75 -37.00-180.00   54
 11  ω    -62.00  25.00   0.50    0.57    --  -47.45  57.00 -90.00  174
 12  ω    -82.00 -33.00   0.50    2.28    -- -106.00  37.00  60.00   98
 13  ω    -62.00  25.00   0.50    0.57    --  -47.45  57.00 150.00  174
 14  ω   -117.00 -33.00   0.50    2.28    -- -106.00 125.00  90.00  168
 15  ω   -129.00 -33.00   0.50    2.28    -- -106.00  77.00 120.00  192
 16  ω   -120.00 -32.00   0.50    0.57    --  -47.45 -57.00   0.00  176
 17  ω   -177.00 -85.00   0.50    2.28    -- -106.00 -77.00 -60.00  184
 18  ω   -177.00-146.00   0.50    2.28    -- -106.00 -19.00  30.00   62
 19  ω   -177.00 -93.00   0.50    2.28    -- -106.00 -19.00  90.00  168
 20  ω   -177.00 -93.00   0.50    2.28    -- -106.00 -19.00-180.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0308820000
_diffrn_orient_matrix_UB_12      0.0949912000
_diffrn_orient_matrix_UB_13      -0.0009906000
_diffrn_orient_matrix_UB_21      0.0098960000
_diffrn_orient_matrix_UB_22      0.0006908000
_diffrn_orient_matrix_UB_23      0.0780370000
_diffrn_orient_matrix_UB_31      0.2492843000
_diffrn_orient_matrix_UB_32      -0.0120644000
_diffrn_orient_matrix_UB_33      -0.0030504000
_diffrn_oxdiff_ac3_digest_frames 
;
017c0dc4ab349a5f2b287ac877a12da33b02740796f
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011f1bbec59933e4265803b30ae582857634ac
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3251
_reflns_number_total             3439
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.4a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.4a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.4a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.055
_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)+(0.0312P)²+0.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F -0.8981(2) -0.85221(8) -0.07325(6) 0.0387(3) Uani 1 1 d . . . . .
O2 O -0.2226(2) -0.54134(9) -0.36510(7) 0.0237(3) Uani 1 1 d . . . . .
O1 O -0.2631(2) -0.65223(9) -0.18060(7) 0.0283(3) Uani 1 1 d . . . . .
N1 N -0.5428(2) -0.60199(9) -0.26747(7) 0.0195(3) Uani 1 1 d . . . . .
C18 C -0.3478(3) -0.51901(12) -0.50072(10) 0.0233(4) Uani 1 1 d . . . . .
C7 C -0.6855(3) -0.65063(11) -0.24256(9) 0.0196(4) Uani 1 1 d . . . . .
C1 C -0.4244(3) -0.69954(11) -0.15406(9) 0.0221(4) Uani 1 1 d . . . . .
C6 C -0.6321(3) -0.70317(11) -0.18422(9) 0.0201(4) Uani 1 1 d . . . . .
C4 C -0.7432(3) -0.79999(11) -0.09930(10) 0.0265(4) Uani 1 1 d . . . . .
C24 C -0.6178(3) -0.69871(12) -0.42321(10) 0.0243(4) Uani 1 1 d . . . . .
C5 C -0.7928(3) -0.75467(11) -0.15628(10) 0.0240(4) Uani 1 1 d . . . . .
C13 C -0.5052(3) -0.52245(11) -0.44947(9) 0.0198(4) Uani 1 1 d . . . . .
C12 C -0.4403(3) -0.56591(11) -0.38337(9) 0.0196(4) Uani 1 1 d . . . . .
C19 C -0.4345(3) -0.65977(11) -0.39589(9) 0.0206(4) Uani 1 1 d . . . . .
C8 C -0.5982(3) -0.54692(11) -0.32345(9) 0.0191(4) Uani 1 1 d . . . . .
C14 C -0.7110(3) -0.48922(11) -0.46265(9) 0.0219(4) Uani 1 1 d . . . . .
C3 C -0.5426(4) -0.79545(12) -0.06763(10) 0.0272(4) Uani 1 1 d . . . . .
C9 C -0.5890(3) -0.45484(12) -0.29886(9) 0.0217(4) Uani 1 1 d . . . . .
C15 C -0.7571(3) -0.45280(11) -0.52503(10) 0.0252(4) Uani 1 1 d . . . . .
C23 C -0.6199(4) -0.78418(13) -0.43401(10) 0.0302(5) Uani 1 1 d . . . . .
C20 C -0.2534(4) -0.70762(13) -0.37965(9) 0.0262(4) Uani 1 1 d . . . . .
C2 C -0.3828(4) -0.74555(12) -0.09537(10) 0.0264(4) Uani 1 1 d . . . . .
C16 C -0.5995(4) -0.45002(12) -0.57515(10) 0.0266(4) Uani 1 1 d . . . . .
C11 C -0.4240(3) -0.43911(13) -0.24201(10) 0.0261(4) Uani 1 1 d . . . . .
C22 C -0.4381(4) -0.83102(12) -0.41781(10) 0.0317(5) Uani 1 1 d . . . . .
C17 C -0.3940(4) -0.48325(12) -0.56291(10) 0.0274(4) Uani 1 1 d . . . . .
C21 C -0.2554(4) -0.79312(13) -0.39100(10) 0.0315(5) Uani 1 1 d . . . . .
C10 C -0.8140(3) -0.42690(13) -0.27484(12) 0.0292(5) Uani 1 1 d . . . . .
H7 H -0.836(4) -0.6521(14) -0.2603(10) 0.020(5) Uiso 1 1 d . . . . .
H2A H -0.238(4) -0.7434(13) -0.0764(10) 0.020(5) Uiso 1 1 d . . . . .
H11A H -0.281(4) -0.4586(15) -0.2541(11) 0.030(6) Uiso 1 1 d . . . . .
H8 H -0.749(3) -0.5586(11) -0.3383(9) 0.011(4) Uiso 1 1 d . . . . .
H14 H -0.822(4) -0.4897(13) -0.4298(11) 0.023(5) Uiso 1 1 d . . . . .
H11B H -0.414(4) -0.3788(15) -0.2345(12) 0.029(6) Uiso 1 1 d . . . . .
H5 H -0.938(4) -0.7566(15) -0.1765(12) 0.035(6) Uiso 1 1 d . . . . .
H20 H -0.125(4) -0.6830(14) -0.3615(12) 0.028(6) Uiso 1 1 d . . . . .
H18 H -0.209(4) -0.5430(15) -0.4903(11) 0.025(5) Uiso 1 1 d . . . . .
H10A H -0.921(4) -0.4270(15) -0.3131(13) 0.035(6) Uiso 1 1 d . . . . .
H21 H -0.128(5) -0.8255(16) -0.3812(12) 0.038(7) Uiso 1 1 d . . . . .
H16 H -0.627(4) -0.4243(14) -0.6189(12) 0.030(6) Uiso 1 1 d . . . . .
H11C H -0.475(4) -0.4652(14) -0.2000(13) 0.028(6) Uiso 1 1 d . . . . .
H10B H -0.808(4) -0.3693(16) -0.2574(12) 0.035(6) Uiso 1 1 d . . . . .
H17 H -0.282(4) -0.4805(14) -0.5985(12) 0.031(6) Uiso 1 1 d . . . . .
H3 H -0.522(4) -0.8273(15) -0.0277(13) 0.032(6) Uiso 1 1 d . . . . .
H24 H -0.749(5) -0.6677(16) -0.4341(12) 0.040(7) Uiso 1 1 d . . . . .
H10C H -0.863(4) -0.4658(17) -0.2372(13) 0.040(7) Uiso 1 1 d . . . . .
H9 H -0.549(3) -0.4189(13) -0.3388(11) 0.020(5) Uiso 1 1 d . . . . .
H15 H -0.900(4) -0.4305(13) -0.5328(11) 0.026(6) Uiso 1 1 d . . . . .
H23 H -0.751(5) -0.8104(15) -0.4556(12) 0.036(6) Uiso 1 1 d . . . . .
H22 H -0.443(4) -0.8912(16) -0.4256(13) 0.041(7) Uiso 1 1 d . . . . .
H2 H -0.219(6) -0.488(2) -0.3686(17) 0.078(11) Uiso 1 1 d . . . . .
H1 H -0.334(6) -0.623(2) -0.2224(17) 0.069(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.368(2) . ?
O2 C12 1.437(2) . ?
O2 H2 0.86(4) . ?
O1 C1 1.353(2) . ?
O1 H1 1.05(3) . ?
N1 C7 1.272(2) . ?
N1 C8 1.456(2) . ?
C18 C13 1.398(3) . ?
C18 C17 1.384(3) . ?
C18 H18 0.95(3) . ?
C7 C6 1.465(3) . ?
C7 H7 0.99(2) . ?
C1 C6 1.406(3) . ?
C1 C2 1.398(3) . ?
C6 C5 1.400(3) . ?
C4 C5 1.374(3) . ?
C4 C3 1.380(3) . ?
C24 C19 1.394(3) . ?
C24 C23 1.392(3) . ?
C24 H24 0.97(3) . ?
C5 H5 0.98(3) . ?
C13 C12 1.532(3) . ?
C13 C14 1.394(3) . ?
C12 C19 1.531(2) . ?
C12 C8 1.558(2) . ?
C19 C20 1.388(3) . ?
C8 C9 1.560(2) . ?
C8 H8 0.99(2) . ?
C14 C15 1.392(3) . ?
C14 H14 0.94(2) . ?
C3 C2 1.380(3) . ?
C3 H3 0.95(3) . ?
C9 C11 1.531(3) . ?
C9 C10 1.525(3) . ?
C9 H9 1.01(2) . ?
C15 C16 1.383(3) . ?
C15 H15 0.96(2) . ?
C23 C22 1.382(3) . ?
C23 H23 1.00(3) . ?
C20 C21 1.394(3) . ?
C20 H20 0.95(3) . ?
C2 H2A 0.97(2) . ?
C16 C17 1.389(3) . ?
C16 H16 0.97(2) . ?
C11 H11A 0.96(3) . ?
C11 H11B 0.98(2) . ?
C11 H11C 0.98(3) . ?
C22 C21 1.380(3) . ?
C22 H22 0.98(3) . ?
C17 H17 0.98(2) . ?
C21 H21 0.96(3) . ?
C10 H10A 1.00(3) . ?
C10 H10B 0.99(3) . ?
C10 H10C 1.02(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 H2 106(3) . . ?
C1 O1 H1 105.0(19) . . ?
C7 N1 C8 120.47(15) . . ?
C13 C18 H18 116.2(13) . . ?
C17 C18 C13 121.05(19) . . ?
C17 C18 H18 122.7(13) . . ?
N1 C7 C6 120.33(16) . . ?
N1 C7 H7 121.4(13) . . ?
C6 C7 H7 118.3(13) . . ?
O1 C1 C6 121.39(16) . . ?
O1 C1 C2 119.04(17) . . ?
C2 C1 C6 119.57(18) . . ?
C1 C6 C7 120.70(17) . . ?
C5 C6 C7 119.59(17) . . ?
C5 C6 C1 119.65(17) . . ?
F1 C4 C5 118.65(18) . . ?
F1 C4 C3 118.71(17) . . ?
C5 C4 C3 122.64(19) . . ?
C19 C24 H24 121.4(15) . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24 117.9(15) . . ?
C6 C5 H5 120.0(15) . . ?
C4 C5 C6 118.71(18) . . ?
C4 C5 H5 121.3(15) . . ?
C18 C13 C12 117.01(17) . . ?
C14 C13 C18 118.29(17) . . ?
C14 C13 C12 124.66(17) . . ?
O2 C12 C13 109.19(14) . . ?
O2 C12 C19 106.88(15) . . ?
O2 C12 C8 109.41(14) . . ?
C13 C12 C8 113.26(15) . . ?
C19 C12 C13 108.61(14) . . ?
C19 C12 C8 109.29(15) . . ?
C24 C19 C12 119.15(17) . . ?
C20 C19 C24 118.94(17) . . ?
C20 C19 C12 121.90(17) . . ?
N1 C8 C12 108.13(14) . . ?
N1 C8 C9 109.51(14) . . ?
N1 C8 H8 109.1(11) . . ?
C12 C8 C9 113.57(15) . . ?
C12 C8 H8 108.6(10) . . ?
C9 C8 H8 107.9(11) . . ?
C13 C14 H14 121.5(13) . . ?
C15 C14 C13 120.65(18) . . ?
C15 C14 H14 117.8(13) . . ?
C4 C3 H3 117.7(15) . . ?
C2 C3 C4 118.88(18) . . ?
C2 C3 H3 123.4(15) . . ?
C8 C9 H9 108.1(12) . . ?
C11 C9 C8 114.10(16) . . ?
C11 C9 H9 108.6(12) . . ?
C10 C9 C8 110.13(16) . . ?
C10 C9 C11 108.71(16) . . ?
C10 C9 H9 107.0(12) . . ?
C14 C15 H15 118.9(14) . . ?
C16 C15 C14 120.28(19) . . ?
C16 C15 H15 120.8(14) . . ?
C24 C23 H23 119.3(15) . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 H23 120.9(15) . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 121.1(14) . . ?
C21 C20 H20 118.7(14) . . ?
C1 C2 H2A 118.0(12) . . ?
C3 C2 C1 120.51(19) . . ?
C3 C2 H2A 121.4(12) . . ?
C15 C16 C17 119.74(18) . . ?
C15 C16 H16 121.9(14) . . ?
C17 C16 H16 118.3(14) . . ?
C9 C11 H11A 111.5(13) . . ?
C9 C11 H11B 108.3(14) . . ?
C9 C11 H11C 109.8(13) . . ?
H11A C11 H11B 108(2) . . ?
H11A C11 H11C 111(2) . . ?
H11B C11 H11C 108.4(19) . . ?
C23 C22 H22 118.6(16) . . ?
C21 C22 C23 120.08(18) . . ?
C21 C22 H22 121.3(16) . . ?
C18 C17 C16 119.99(19) . . ?
C18 C17 H17 120.5(14) . . ?
C16 C17 H17 119.5(14) . . ?
C20 C21 H21 119.7(15) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 120.0(15) . . ?
C9 C10 H10A 110.9(14) . . ?
C9 C10 H10B 110.4(15) . . ?
C9 C10 H10C 108.3(15) . . ?
H10A C10 H10B 107(2) . . ?
H10A C10 H10C 111(2) . . ?
H10B C10 H10C 110(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.461
####################################################################### 
# 
# 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_exp_850_harveymudd_2
_database_code_depnum_ccdc_archive 'CCDC 1837508'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H24 F N O2'
_chemical_formula_sum            'C28 H24 F N O2'
_chemical_formula_weight         425.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H25 N1 O2 F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.93196(5)
_cell_length_b                   18.49475(19)
_cell_length_c                   20.30007(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2227.12(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18874
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.2940
_cell_measurement_theta_min      4.3240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20287
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.356
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 177.00   0.50    1.06    --  105.75 137.00  91.00  186
  2  ω     92.00 177.00   0.50    1.06    --  105.75 125.00  60.00  170
  3  ω     33.00  65.00   0.50    1.06    --  105.75 -37.00 120.00   64
  4  ω     33.00  65.00   0.50    1.06    --  105.75 -37.00  90.00   64
  5  ω     34.00 120.00   0.50    1.06    --  105.75 -57.00  60.00  172
  6  ω     34.00 120.00   0.50    1.06    --  105.75 -57.00 -30.00  172
  7  ω    -23.00  60.00   0.50    0.26    --   49.15 -37.00-180.00  166
  8  ω   -121.00 -63.00   0.50    0.26    --  -49.15-137.00  28.00  116
  9  ω   -120.00 -66.00   0.50    0.26    --  -49.15-132.00-154.00  108
 10  ω   -120.00 -35.00   0.50    0.26    --  -49.15 -57.00   0.00  170
 11  ω   -156.00 -62.00   0.50    1.06    --  -84.25 -77.00 -30.00  188
 12  ω   -156.00-100.00   0.50    1.06    --  -84.25 -77.00 120.00  112
 13  ω     35.00 121.00   0.50    0.26    --   49.15  57.00 120.00  172
 14  ω     95.00 178.00   0.50    1.06    --  105.75  37.00  30.00  166
 15  ω     28.00 121.00   0.50    0.26    --   49.15  77.00-150.00  186
 16  ω     95.00 178.00   0.50    1.06    --  105.75  19.00-150.00  166
 17  ω     95.00 178.00   0.50    1.06    --  105.75  19.00 -90.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1283734000
_diffrn_orient_matrix_UB_12      -0.0358812000
_diffrn_orient_matrix_UB_13      0.0572662000
_diffrn_orient_matrix_UB_21      -0.2256724000
_diffrn_orient_matrix_UB_22      0.0220690000
_diffrn_orient_matrix_UB_23      -0.0317028000
_diffrn_orient_matrix_UB_31      -0.0050056000
_diffrn_orient_matrix_UB_32      -0.0718877000
_diffrn_orient_matrix_UB_33      -0.0383757000
_diffrn_oxdiff_ac3_digest_frames 
;
01657f4d68fddf9c0b4992ce2aa17a46b2025449fe8
;
_diffrn_oxdiff_ac3_digest_hkl    
;
014d3ab6a371f4dc426d453d6c1861b84c933e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3901
_reflns_number_total             3962
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.069
_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)+(0.0289P)²+0.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C17(H17), C32(H32), C23(H23), C30(H30), C8(H8), C25(H25),
 C14(H14), C16(H16), C22(H22), C0AA(H0AA), C7(H7), C12(H12), C13(H13), C10(H10),
  C6(H6), C5(H5), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F 0.90678(18) 0.16637(5) 0.12583(5) 0.0311(3) Uani 1 1 d . . . . .
O1 O 0.23006(18) 0.48603(6) 0.35059(5) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.27415(19) 0.37391(6) 0.17833(5) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.5561(2) 0.43271(7) 0.25759(6) 0.0169(3) Uani 1 1 d . . . . .
C19 C 0.6995(2) 0.38358(8) 0.24430(7) 0.0169(3) Uani 1 1 d . . . . .
H19 H 0.8405 0.3846 0.2643 0.020 Uiso 1 1 calc R . . . .
C24 C 0.7526(3) 0.21976(8) 0.13882(7) 0.0218(3) Uani 1 1 d . . . . .
C15 C 0.5238(2) 0.52338(8) 0.42643(7) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.4871(2) 0.39584(8) 0.38833(7) 0.0178(3) Uani 1 1 d . . . . .
C21 C 0.4353(3) 0.32440(8) 0.16553(7) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.4625(2) 0.47490(8) 0.36794(7) 0.0168(3) Uani 1 1 d . . . . .
C18 C 0.7331(3) 0.55605(8) 0.43480(7) 0.0196(3) Uani 1 1 d . . . . .
H18 H 0.8435 0.5503 0.4027 0.023 Uiso 1 1 calc R . . . .
C17 C 0.7795(3) 0.59729(8) 0.49061(8) 0.0227(3) Uani 1 1 d . . . . .
H17 H 0.9197 0.6192 0.4953 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7148(3) 0.57787(8) 0.21479(7) 0.0190(3) Uani 1 1 d . . . . .
C20 C 0.6456(3) 0.32568(8) 0.19809(7) 0.0172(3) Uani 1 1 d . . . . .
C32 C 0.3627(3) 0.53215(8) 0.47617(7) 0.0200(3) Uani 1 1 d . . . . .
H32 H 0.2224 0.5102 0.4718 0.024 Uiso 1 1 calc R . . . .
C23 C 0.5528(3) 0.21921(8) 0.10437(8) 0.0228(3) Uani 1 1 d . . . . .
H23 H 0.5257 0.1843 0.0724 0.027 Uiso 1 1 calc R . . . .
C30 C 0.6177(3) 0.60574(9) 0.53906(8) 0.0239(4) Uani 1 1 d . . . . .
H30 H 0.6486 0.6332 0.5763 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6475(3) 0.55695(8) 0.15166(8) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.5101 0.5336 0.1458 0.027 Uiso 1 1 calc R . . . .
C25 C 0.8046(3) 0.27168(8) 0.18477(7) 0.0194(3) Uani 1 1 d . . . . .
H25 H 0.9424 0.2710 0.2066 0.023 Uiso 1 1 calc R . . . .
C14 C 0.6892(3) 0.37171(9) 0.41540(8) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.8051 0.4045 0.4232 0.026 Uiso 1 1 calc R . . . .
C16 C 0.4086(3) 0.57287(9) 0.53168(8) 0.0231(3) Uani 1 1 d . . . . .
H16 H 0.2993 0.5783 0.5642 0.028 Uiso 1 1 calc R . . . .
C2 C 0.6119(2) 0.48842(8) 0.30539(7) 0.0165(3) Uani 1 1 d . . . . .
H2A H 0.7715 0.4845 0.3174 0.020 Uiso 1 1 calc R . . . .
C22 C 0.3936(3) 0.27139(9) 0.11807(8) 0.0229(3) Uani 1 1 d . . . . .
H22 H 0.2572 0.2713 0.0955 0.027 Uiso 1 1 calc R . . . .
C0AA C 0.9217(3) 0.61248(9) 0.22201(8) 0.0244(3) Uani 1 1 d . . . . .
H0AA H 0.9691 0.6267 0.2637 0.029 Uiso 1 1 calc R . . . .
C3 C 0.5678(3) 0.56287(8) 0.27401(7) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.4109 0.5656 0.2608 0.024 Uiso 1 1 calc R . . . .
H3B H 0.5937 0.6001 0.3068 0.024 Uiso 1 1 calc R . . . .
C7 C 0.7846(3) 0.57077(9) 0.09767(8) 0.0268(4) Uani 1 1 d . . . . .
H7 H 0.7381 0.5568 0.0558 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5483(3) 0.25013(9) 0.41943(9) 0.0298(4) Uani 1 1 d . . . . .
H12 H 0.5680 0.2016 0.4300 0.036 Uiso 1 1 calc R . . . .
C13 C 0.7194(3) 0.29925(9) 0.43085(8) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.8551 0.2837 0.4489 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3160(3) 0.34590(9) 0.37683(9) 0.0267(4) Uani 1 1 d . . . . .
H10 H 0.1800 0.3611 0.3587 0.032 Uiso 1 1 calc R . . . .
C6 C 0.9903(3) 0.60527(9) 0.10572(8) 0.0282(4) Uani 1 1 d . . . . .
H6 H 1.0819 0.6143 0.0695 0.034 Uiso 1 1 calc R . . . .
C5 C 1.0581(3) 0.62609(9) 0.16794(9) 0.0286(4) Uani 1 1 d . . . . .
H5 H 1.1958 0.6493 0.1736 0.034 Uiso 1 1 calc R . . . .
C11 C 0.3475(3) 0.27364(10) 0.39225(10) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.2325 0.2406 0.3843 0.041 Uiso 1 1 calc R . . . .
H1 H 0.218(4) 0.5312(15) 0.3459(12) 0.052(7) Uiso 1 1 d . . . . .
H2 H 0.339(5) 0.4077(16) 0.2093(15) 0.074(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C24 1.3717(18) . ?
O1 C1 1.4377(18) . ?
O1 H1 0.84(3) . ?
O2 C21 1.3492(19) . ?
O2 H2 0.97(3) . ?
N1 C19 1.274(2) . ?
N1 C2 1.4534(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.459(2) . ?
C24 C23 1.376(2) . ?
C24 C25 1.374(2) . ?
C15 C1 1.532(2) . ?
C15 C18 1.391(2) . ?
C15 C32 1.400(2) . ?
C9 C1 1.527(2) . ?
C9 C14 1.392(2) . ?
C9 C10 1.392(2) . ?
C21 C20 1.412(2) . ?
C21 C22 1.397(2) . ?
C1 C2 1.569(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C30 1.383(2) . ?
C4 C8 1.397(2) . ?
C4 C0AA 1.392(2) . ?
C4 C3 1.511(2) . ?
C20 C25 1.400(2) . ?
C32 H32 0.9300 . ?
C32 C16 1.382(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.379(2) . ?
C30 H30 0.9300 . ?
C30 C16 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.388(2) . ?
C25 H25 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.388(2) . ?
C16 H16 0.9300 . ?
C2 H2A 0.9800 . ?
C2 C3 1.540(2) . ?
C22 H22 0.9300 . ?
C0AA H0AA 0.9300 . ?
C0AA C5 1.387(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C6 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C12 C11 1.383(3) . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(3) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 104.5(18) . . ?
C21 O2 H2 106.3(17) . . ?
C19 N1 C2 119.67(13) . . ?
N1 C19 H19 119.5 . . ?
N1 C19 C20 120.91(13) . . ?
C20 C19 H19 119.5 . . ?
F1 C24 C23 118.11(13) . . ?
F1 C24 C25 118.95(14) . . ?
C25 C24 C23 122.93(15) . . ?
C18 C15 C1 124.11(13) . . ?
C18 C15 C32 118.10(14) . . ?
C32 C15 C1 117.70(13) . . ?
C14 C9 C1 119.78(13) . . ?
C14 C9 C10 118.76(15) . . ?
C10 C9 C1 121.34(14) . . ?
O2 C21 C20 121.63(13) . . ?
O2 C21 C22 118.93(14) . . ?
C22 C21 C20 119.42(15) . . ?
O1 C1 C15 109.49(12) . . ?
O1 C1 C9 107.18(12) . . ?
O1 C1 C2 108.71(11) . . ?
C15 C1 C2 113.58(12) . . ?
C9 C1 C15 109.13(12) . . ?
C9 C1 C2 108.54(12) . . ?
C15 C18 H18 119.6 . . ?
C15 C18 C17 120.90(14) . . ?
C17 C18 H18 119.6 . . ?
C18 C17 H17 119.9 . . ?
C30 C17 C18 120.20(15) . . ?
C30 C17 H17 119.9 . . ?
C8 C4 C3 120.96(14) . . ?
C0AA C4 C8 118.41(15) . . ?
C0AA C4 C3 120.63(14) . . ?
C21 C20 C19 120.45(13) . . ?
C25 C20 C19 120.03(14) . . ?
C25 C20 C21 119.50(14) . . ?
C15 C32 H32 119.5 . . ?
C16 C32 C15 121.09(15) . . ?
C16 C32 H32 119.5 . . ?
C24 C23 H23 120.6 . . ?
C24 C23 C22 118.82(14) . . ?
C22 C23 H23 120.6 . . ?
C17 C30 H30 120.2 . . ?
C17 C30 C16 119.56(14) . . ?
C16 C30 H30 120.2 . . ?
C4 C8 H8 119.8 . . ?
C7 C8 C4 120.41(15) . . ?
C7 C8 H8 119.8 . . ?
C24 C25 C20 118.61(14) . . ?
C24 C25 H25 120.7 . . ?
C20 C25 H25 120.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.67(15) . . ?
C13 C14 H14 119.7 . . ?
C32 C16 C30 120.15(15) . . ?
C32 C16 H16 119.9 . . ?
C30 C16 H16 119.9 . . ?
N1 C2 C1 107.37(11) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 C3 108.61(11) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 C1 112.42(12) . . ?
C3 C2 H2A 109.5 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.62(15) . . ?
C23 C22 H22 119.7 . . ?
C4 C0AA H0AA 119.5 . . ?
C5 C0AA C4 120.98(16) . . ?
C5 C0AA H0AA 119.5 . . ?
C4 C3 C2 113.29(12) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.46(15) . . ?
C6 C7 H7 119.8 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.53(16) . . ?
C11 C12 H12 120.2 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.14(16) . . ?
C12 C13 H13 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.26(16) . . ?
C11 C10 H10 119.9 . . ?
C7 C6 H6 120.2 . . ?
C5 C6 C7 119.52(15) . . ?
C5 C6 H6 120.2 . . ?
C0AA C5 H5 119.9 . . ?
C6 C5 C0AA 120.23(16) . . ?
C6 C5 H5 119.9 . . ?
C12 C11 C10 120.63(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?

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
F1 C24 C23 C22 178.32(14) . . . . ?
F1 C24 C25 C20 -179.54(13) . . . . ?
O1 C1 C2 N1 -65.40(15) . . . . ?
O1 C1 C2 C3 53.99(15) . . . . ?
O2 C21 C20 C19 -3.4(2) . . . . ?
O2 C21 C20 C25 177.83(14) . . . . ?
O2 C21 C22 C23 -178.98(14) . . . . ?
N1 C19 C20 C21 2.1(2) . . . . ?
N1 C19 C20 C25 -179.20(14) . . . . ?
N1 C2 C3 C4 -62.97(16) . . . . ?
C19 N1 C2 C1 -110.28(14) . . . . ?
C19 N1 C2 C3 127.92(14) . . . . ?
C19 C20 C25 C24 -177.11(14) . . . . ?
C24 C23 C22 C21 0.7(2) . . . . ?
C15 C1 C2 N1 172.44(12) . . . . ?
C15 C1 C2 C3 -68.17(15) . . . . ?
C15 C18 C17 C30 0.7(2) . . . . ?
C15 C32 C16 C30 -0.2(2) . . . . ?
C9 C1 C2 N1 50.87(15) . . . . ?
C9 C1 C2 C3 170.26(12) . . . . ?
C9 C14 C13 C12 0.0(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C21 C20 C25 C24 1.6(2) . . . . ?
C1 C15 C18 C17 -177.54(14) . . . . ?
C1 C15 C32 C16 177.57(14) . . . . ?
C1 C9 C14 C13 -176.38(14) . . . . ?
C1 C9 C10 C11 176.20(16) . . . . ?
C1 C2 C3 C4 178.37(12) . . . . ?
C18 C15 C1 O1 -144.62(14) . . . . ?
C18 C15 C1 C9 98.34(16) . . . . ?
C18 C15 C1 C2 -22.90(19) . . . . ?
C18 C15 C32 C16 0.8(2) . . . . ?
C18 C17 C30 C16 0.0(2) . . . . ?
C17 C30 C16 C32 -0.2(2) . . . . ?
C4 C8 C7 C6 0.2(2) . . . . ?
C4 C0AA C5 C6 -0.1(2) . . . . ?
C20 C21 C22 C23 2.1(2) . . . . ?
C32 C15 C1 O1 38.87(17) . . . . ?
C32 C15 C1 C9 -78.17(16) . . . . ?
C32 C15 C1 C2 160.59(13) . . . . ?
C32 C15 C18 C17 -1.0(2) . . . . ?
C23 C24 C25 C20 1.2(2) . . . . ?
C8 C4 C0AA C5 0.1(2) . . . . ?
C8 C4 C3 C2 88.32(17) . . . . ?
C8 C7 C6 C5 -0.2(2) . . . . ?
C25 C24 C23 C22 -2.5(2) . . . . ?
C14 C9 C1 O1 -172.18(13) . . . . ?
C14 C9 C1 C15 -53.69(17) . . . . ?
C14 C9 C1 C2 70.56(16) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?
C2 N1 C19 C20 178.07(13) . . . . ?
C22 C21 C20 C19 175.49(14) . . . . ?
C22 C21 C20 C25 -3.2(2) . . . . ?
C0AA C4 C8 C7 -0.2(2) . . . . ?
C0AA C4 C3 C2 -91.19(16) . . . . ?
C3 C4 C8 C7 -179.71(14) . . . . ?
C3 C4 C0AA C5 179.64(15) . . . . ?
C7 C6 C5 C0AA 0.1(2) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C10 C9 C1 O1 11.74(19) . . . . ?
C10 C9 C1 C15 130.22(14) . . . . ?
C10 C9 C1 C2 -105.52(16) . . . . ?
C10 C9 C14 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
150 mu Mitegen loop
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.722
####################################################################### 
# 
# 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_exp_849_harveymudd_1
_database_code_depnum_ccdc_archive 'CCDC 1837507'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;
_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H41 N O2'
_chemical_formula_sum            'C36 H41 N O2'
_chemical_formula_weight         519.70
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C144 H164 N4 O8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.77210(10)
_cell_length_b                   11.08970(10)
_cell_length_c                   27.2621(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2954.38(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24422
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.0940
_cell_measurement_theta_min      4.2770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27404
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.304
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 HyPix-6000HE
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -10.00   0.50    1.20    --  -84.25  19.00 -60.00   96
  2  ω    -71.00  23.00   0.50    0.30    --  -49.03  77.00 120.00  188
  3  ω    -59.00  23.00   0.50    0.30    --  -49.03  37.00  30.00  164
  4  ω     35.00 120.00   0.50    0.30    --   49.03  57.00-120.00  170
  5  ω    102.00 177.00   0.50    1.20    --  105.75 105.00 -78.00  150
  6  ω     34.00 110.00   0.50    1.20    --  105.75 -99.00   0.00  152
  7  ω     34.00 110.00   0.50    1.20    --  105.75 -99.00  60.00  152
  8  ω     33.00  65.00   0.50    1.20    --  105.75 -37.00   0.00   64
  9  ω     33.00  65.00   0.50    1.20    --  105.75 -37.00  30.00   64
 10  ω     34.00 110.00   0.50    1.20    --  105.75 -99.00 -30.00  152
 11  ω     34.00 128.00   0.50    1.20    --  105.75 -77.00-180.00  188
 12  ω     34.00 120.00   0.50    1.20    --  105.75 -57.00-180.00  172
 13  ω     33.00  65.00   0.50    1.20    --  105.75 -37.00-150.00   64
 14  ω   -120.00 -27.00   0.50    0.30    --  -49.03 -77.00  30.00  186
 15  ω   -157.00 -73.00   0.50    1.20    --  -84.25 -37.00-150.00  168
 16  ω   -159.00 -73.00   0.50    1.20    --  -84.25 -19.00 -60.00  172
 17  ω   -159.00 -73.00   0.50    1.20    --  -84.25 -19.00 120.00  172
 18  ω   -156.00-131.00   0.50    1.20    --  -84.25 -57.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0939219000
_diffrn_orient_matrix_UB_12      0.0827243000
_diffrn_orient_matrix_UB_13      -0.0304564000
_diffrn_orient_matrix_UB_21      -0.1198749000
_diffrn_orient_matrix_UB_22      -0.0880356000
_diffrn_orient_matrix_UB_23      0.0079923000
_diffrn_orient_matrix_UB_31      -0.0406949000
_diffrn_orient_matrix_UB_32      0.0686696000
_diffrn_orient_matrix_UB_33      0.0469131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5186
_reflns_number_total             5277
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 2213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_coef       0.00125(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5277
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.5851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0686
_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
 C33-C34 \\sim C33-C35 \\sim C33-C36 \\sim C33-C34A \\sim C33-C35A \\sim
C33-C36A
 with sigma of 0.02
 C34-C35 \\sim C34-C36 \\sim C35-C36 \\sim C34A-C35A \\sim C34A-C36A \\sim
C35A-C36A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C34 \\sim C34A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C35 \\sim C35A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C36 \\sim C36A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C35) = Uanis(C35A)
Uanis(C35) = Uanis(C36A)
4. Rigid body (RIGU) restrains
 C34A, H34D, H34E, H34F, C35A, H35D, H35E, H35F, C36A, H36D, H36E, H36F
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C34A)=Sof(H34D)=Sof(H34E)=Sof(H34F)=Sof(C35A)=Sof(H35D)=Sof(H35E)=
 Sof(H35F)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2A)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C26(H26), C28(H28)
6.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C34A(H34D,H34E,H34F),
 C35A(H35D,H35E,H35F), C36A(H36D,H36E,H36F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.56811(13) 0.21215(10) 0.70159(5) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.530(2) 0.212(2) 0.6728(9) 0.037(6) Uiso 1 1 d . . . . .
O2 O 0.25552(12) 0.22337(10) 0.60532(4) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.296(2) 0.256(2) 0.6349(10) 0.047(7) Uiso 1 1 d . . . . .
N1 N 0.36680(14) 0.36641(12) 0.66775(5) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.57364(17) 0.33624(14) 0.71604(6) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.42474(16) 0.38596(14) 0.71638(6) 0.0187(3) Uani 1 1 d . . . . .
H2A H 0.4261 0.4725 0.7236 0.022 Uiso 1 1 calc R . . . .
C3 C 0.33279(17) 0.32034(15) 0.75400(6) 0.0220(3) Uani 1 1 d . . . . .
H3A H 0.2993 0.2459 0.7397 0.026 Uiso 1 1 calc R . . . .
H3B H 0.3867 0.2999 0.7827 0.026 Uiso 1 1 calc R . . . .
C4 C 0.21265(17) 0.39714(14) 0.76939(6) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.21672(19) 0.45762(16) 0.81407(6) 0.0270(4) Uani 1 1 d . . . . .
H5 H 0.2916 0.4473 0.8347 0.032 Uiso 1 1 calc R . . . .
C6 C 0.1108(2) 0.53314(17) 0.82833(7) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.1143 0.5716 0.8586 0.039 Uiso 1 1 calc R . . . .
C7 C 0.00001(19) 0.55132(17) 0.79763(8) 0.0337(4) Uani 1 1 d . . . . .
H7 H -0.0698 0.6037 0.8068 0.040 Uiso 1 1 calc R . . . .
C8 C -0.00632(19) 0.49124(17) 0.75327(8) 0.0334(4) Uani 1 1 d . . . . .
H8 H -0.0810 0.5026 0.7326 0.040 Uiso 1 1 calc R . . . .
C9 C 0.09884(17) 0.41387(17) 0.73941(7) 0.0271(4) Uani 1 1 d . . . . .
H9 H 0.0931 0.3728 0.7097 0.032 Uiso 1 1 calc R . . . .
C10 C 0.66727(17) 0.40802(15) 0.68132(6) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.77282(19) 0.34900(16) 0.65679(6) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.7813 0.2658 0.6597 0.032 Uiso 1 1 calc R . . . .
C12 C 0.86551(19) 0.41218(19) 0.62811(6) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.9351 0.3712 0.6119 0.038 Uiso 1 1 calc R . . . .
C13 C 0.8546(2) 0.53627(19) 0.62357(6) 0.0326(4) Uani 1 1 d . . . . .
H13 H 0.9161 0.5788 0.6041 0.039 Uiso 1 1 calc R . . . .
C14 C 0.7514(2) 0.59612(17) 0.64821(6) 0.0304(4) Uani 1 1 d . . . . .
H14 H 0.7442 0.6795 0.6455 0.037 Uiso 1 1 calc R . . . .
C15 C 0.65843(18) 0.53308(15) 0.67690(6) 0.0236(3) Uani 1 1 d . . . . .
H15 H 0.5896 0.5746 0.6933 0.028 Uiso 1 1 calc R . . . .
C16 C 0.64150(17) 0.33926(14) 0.76652(6) 0.0202(3) Uani 1 1 d . . . . .
C17 C 0.73479(18) 0.24955(15) 0.77938(6) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.7493 0.1846 0.7584 0.030 Uiso 1 1 calc R . . . .
C18 C 0.80635(19) 0.25662(17) 0.82341(7) 0.0307(4) Uani 1 1 d . . . . .
H18 H 0.8691 0.1969 0.8316 0.037 Uiso 1 1 calc R . . . .
C19 C 0.7846(2) 0.35198(17) 0.85506(7) 0.0323(4) Uani 1 1 d . . . . .
H19 H 0.8324 0.3564 0.8845 0.039 Uiso 1 1 calc R . . . .
C20 C 0.69136(19) 0.44085(17) 0.84284(6) 0.0294(4) Uani 1 1 d . . . . .
H20 H 0.6755 0.5044 0.8643 0.035 Uiso 1 1 calc R . . . .
C21 C 0.62146(18) 0.43548(15) 0.79862(6) 0.0237(4) Uani 1 1 d . . . . .
H21 H 0.5606 0.4967 0.7903 0.028 Uiso 1 1 calc R . . . .
C22 C 0.32793(16) 0.45490(14) 0.64111(6) 0.0191(3) Uani 1 1 d . . . . .
H22 H 0.3410 0.5331 0.6525 0.023 Uiso 1 1 calc R . . . .
C23 C 0.26383(16) 0.43710(14) 0.59340(6) 0.0181(3) Uani 1 1 d . . . . .
C24 C 0.23060(16) 0.32044(14) 0.57636(5) 0.0176(3) Uani 1 1 d . . . . .
C25 C 0.17216(15) 0.30443(14) 0.52971(6) 0.0179(3) Uani 1 1 d . . . . .
C26 C 0.14936(16) 0.40795(14) 0.50198(6) 0.0189(3) Uani 1 1 d . . . . .
H26 H 0.1110 0.3986 0.4710 0.023 Uiso 1 1 calc R . . . .
C27 C 0.18020(16) 0.52530(14) 0.51753(6) 0.0189(3) Uani 1 1 d . . . . .
C28 C 0.23731(16) 0.53753(14) 0.56375(6) 0.0186(3) Uani 1 1 d . . . . .
H28 H 0.2585 0.6141 0.5754 0.022 Uiso 1 1 calc R . . . .
C29 C 0.13769(17) 0.17833(14) 0.50978(6) 0.0217(3) Uani 1 1 d . . . . .
C30 C 0.26696(18) 0.09971(15) 0.50799(6) 0.0253(4) Uani 1 1 d . . . . .
H30A H 0.3345 0.1379 0.4877 0.038 Uiso 1 1 calc GR . . . .
H30B H 0.2445 0.0221 0.4947 0.038 Uiso 1 1 calc GR . . . .
H30C H 0.3027 0.0900 0.5406 0.038 Uiso 1 1 calc GR . . . .
C31 C 0.02999(19) 0.11761(16) 0.54277(7) 0.0303(4) Uani 1 1 d . . . . .
H31A H 0.0660 0.1091 0.5753 0.045 Uiso 1 1 calc GR . . . .
H31B H 0.0079 0.0395 0.5298 0.045 Uiso 1 1 calc GR . . . .
H31C H -0.0511 0.1664 0.5437 0.045 Uiso 1 1 calc GR . . . .
C32 C 0.08018(18) 0.18382(16) 0.45755(7) 0.0271(4) Uani 1 1 d . . . . .
H32A H -0.0026 0.2305 0.4574 0.041 Uiso 1 1 calc GR . . . .
H32B H 0.0609 0.1036 0.4462 0.041 Uiso 1 1 calc GR . . . .
H32C H 0.1461 0.2208 0.4362 0.041 Uiso 1 1 calc GR . . . .
C33 C 0.15771(18) 0.63324(15) 0.48320(6) 0.0229(4) Uani 1 1 d D . . . .
C34 C 0.0224(6) 0.6236(5) 0.4565(2) 0.0572(16) Uani 0.715(6) 1 d D U P A 1
H34A H 0.0223 0.5524 0.4365 0.086 Uiso 0.715(6) 1 calc GR . P A 1
H34B H 0.0097 0.6933 0.4362 0.086 Uiso 0.715(6) 1 calc GR . P A 1
H34C H -0.0506 0.6188 0.4800 0.086 Uiso 0.715(6) 1 calc GR . P A 1
C35 C 0.1601(5) 0.7534(3) 0.51081(12) 0.0389(8) Uani 0.715(6) 1 d D U P A 1
H35A H 0.0943 0.7513 0.5369 0.058 Uiso 0.715(6) 1 calc GR . P A 1
H35B H 0.1378 0.8177 0.4886 0.058 Uiso 0.715(6) 1 calc GR . P A 1
H35C H 0.2498 0.7666 0.5242 0.058 Uiso 0.715(6) 1 calc GR . P A 1
C36 C 0.2744(6) 0.6324(5) 0.44569(19) 0.0649(16) Uani 0.715(6) 1 d D U P A 1
H36A H 0.3605 0.6364 0.4625 0.097 Uiso 0.715(6) 1 calc GR . P A 1
H36B H 0.2655 0.7007 0.4243 0.097 Uiso 0.715(6) 1 calc GR . P A 1
H36C H 0.2702 0.5596 0.4267 0.097 Uiso 0.715(6) 1 calc GR . P A 1
C34A C 0.0599(10) 0.6039(11) 0.4403(3) 0.027(2) Uani 0.285(6) 1 d D U P A 2
H34D H 0.1021 0.5458 0.4190 0.041 Uiso 0.285(6) 1 calc GR U P A 2
H34E H 0.0409 0.6763 0.4221 0.041 Uiso 0.285(6) 1 calc GR U P A 2
H34F H -0.0240 0.5716 0.4530 0.041 Uiso 0.285(6) 1 calc GR U P A 2
C35A C 0.0933(12) 0.7350(8) 0.5117(3) 0.0389(8) Uani 0.285(6) 1 d D U P A 2
H35D H 0.0068 0.7091 0.5246 0.058 Uiso 0.285(6) 1 calc GR U P A 2
H35E H 0.0796 0.8029 0.4904 0.058 Uiso 0.285(6) 1 calc GR U P A 2
H35F H 0.1526 0.7578 0.5382 0.058 Uiso 0.285(6) 1 calc GR U P A 2
C36A C 0.2917(10) 0.6740(8) 0.4619(3) 0.0389(8) Uani 0.285(6) 1 d D U P A 2
H36D H 0.3540 0.6930 0.4880 0.058 Uiso 0.285(6) 1 calc GR U P A 2
H36E H 0.2771 0.7443 0.4421 0.058 Uiso 0.285(6) 1 calc GR U P A 2
H36F H 0.3295 0.6107 0.4421 0.058 Uiso 0.285(6) 1 calc GR U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.87(2) . ?
O1 C1 1.4323(19) . ?
O2 H2 0.96(3) . ?
O2 C24 1.3570(18) . ?
N1 C2 1.458(2) . ?
N1 C22 1.278(2) . ?
C1 C2 1.556(2) . ?
C1 C10 1.538(2) . ?
C1 C16 1.528(2) . ?
C2 H2A 0.9800 . ?
C2 C3 1.546(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.510(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.393(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(2) . ?
C10 C15 1.395(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(2) . ?
C16 C21 1.394(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.457(2) . ?
C23 C24 1.412(2) . ?
C23 C28 1.400(2) . ?
C24 C25 1.405(2) . ?
C25 C26 1.393(2) . ?
C25 C29 1.538(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.402(2) . ?
C27 C28 1.385(2) . ?
C27 C33 1.535(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.536(2) . ?
C29 C31 1.539(2) . ?
C29 C32 1.532(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.512(4) . ?
C33 C35 1.531(3) . ?
C33 C36 1.531(4) . ?
C33 C34A 1.546(10) . ?
C33 C35A 1.508(9) . ?
C33 C36A 1.502(9) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C34A H34D 0.9600 . ?
C34A H34E 0.9600 . ?
C34A H34F 0.9600 . ?
C35A H35D 0.9600 . ?
C35A H35E 0.9600 . ?
C35A H35F 0.9600 . ?
C36A H36D 0.9600 . ?
C36A H36E 0.9600 . ?
C36A H36F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105.3(15) . . ?
C24 O2 H2 105.3(14) . . ?
C22 N1 C2 121.18(14) . . ?
O1 C1 C2 107.86(13) . . ?
O1 C1 C10 110.51(13) . . ?
O1 C1 C16 106.57(12) . . ?
C10 C1 C2 112.11(13) . . ?
C16 C1 C2 113.13(13) . . ?
C16 C1 C10 106.54(13) . . ?
N1 C2 C1 107.77(12) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 C3 107.92(13) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 C1 112.37(13) . . ?
C3 C2 H2A 109.6 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.77(13) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C5 C4 C3 119.55(15) . . ?
C5 C4 C9 118.20(16) . . ?
C9 C4 C3 122.20(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.01(17) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.16(18) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.62(18) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.13(18) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.84(17) . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C1 119.53(15) . . ?
C11 C10 C15 118.14(16) . . ?
C15 C10 C1 122.06(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.14(17) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.12(18) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.33(18) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.66(18) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.60(17) . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C1 119.64(14) . . ?
C21 C16 C1 121.42(14) . . ?
C21 C16 C17 118.71(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.35(17) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.31(17) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.78(16) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.21(17) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.62(16) . . ?
C20 C21 H21 119.7 . . ?
N1 C22 H22 119.0 . . ?
N1 C22 C23 122.06(14) . . ?
C23 C22 H22 119.0 . . ?
C24 C23 C22 121.10(14) . . ?
C28 C23 C22 119.15(14) . . ?
C28 C23 C24 119.74(14) . . ?
O2 C24 C23 119.60(14) . . ?
O2 C24 C25 119.94(14) . . ?
C25 C24 C23 120.45(14) . . ?
C24 C25 C29 121.59(14) . . ?
C26 C25 C24 116.88(14) . . ?
C26 C25 C29 121.52(14) . . ?
C25 C26 H26 117.7 . . ?
C25 C26 C27 124.52(14) . . ?
C27 C26 H26 117.7 . . ?
C26 C27 C33 120.57(14) . . ?
C28 C27 C26 116.94(14) . . ?
C28 C27 C33 122.41(14) . . ?
C23 C28 H28 119.3 . . ?
C27 C28 C23 121.46(14) . . ?
C27 C28 H28 119.3 . . ?
C25 C29 C31 109.94(13) . . ?
C30 C29 C25 110.33(13) . . ?
C30 C29 C31 109.43(14) . . ?
C32 C29 C25 111.88(14) . . ?
C32 C29 C30 107.15(13) . . ?
C32 C29 C31 108.03(14) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C33 C34A 112.7(5) . . ?
C34 C33 C27 111.3(2) . . ?
C34 C33 C35 108.2(3) . . ?
C34 C33 C36 109.2(3) . . ?
C35 C33 C27 112.13(16) . . ?
C35 C33 C36 108.8(3) . . ?
C36 C33 C27 107.21(17) . . ?
C35A C33 C27 109.2(3) . . ?
C35A C33 C34A 106.8(5) . . ?
C36A C33 C27 110.2(4) . . ?
C36A C33 C34A 108.1(5) . . ?
C36A C33 C35A 109.7(5) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C34A H34D 109.5 . . ?
C33 C34A H34E 109.5 . . ?
C33 C34A H34F 109.5 . . ?
H34D C34A H34E 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
C33 C35A H35D 109.5 . . ?
C33 C35A H35E 109.5 . . ?
C33 C35A H35F 109.5 . . ?
H35D C35A H35E 109.5 . . ?
H35D C35A H35F 109.5 . . ?
H35E C35A H35F 109.5 . . ?
C33 C36A H36D 109.5 . . ?
C33 C36A H36E 109.5 . . ?
C33 C36A H36F 109.5 . . ?
H36D C36A H36E 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -56.43(16) . . . . ?
O1 C1 C2 C3 62.34(16) . . . . ?
O1 C1 C10 C11 -26.7(2) . . . . ?
O1 C1 C10 C15 159.43(15) . . . . ?
O1 C1 C16 C17 28.4(2) . . . . ?
O1 C1 C16 C21 -157.23(15) . . . . ?
O2 C24 C25 C26 179.98(14) . . . . ?
O2 C24 C25 C29 -1.2(2) . . . . ?
N1 C2 C3 C4 -84.85(16) . . . . ?
N1 C22 C23 C24 5.8(2) . . . . ?
N1 C22 C23 C28 -173.06(15) . . . . ?
C1 C2 C3 C4 156.48(13) . . . . ?
C1 C10 C11 C12 -175.12(15) . . . . ?
C1 C10 C15 C14 174.89(15) . . . . ?
C1 C16 C17 C18 174.39(15) . . . . ?
C1 C16 C21 C20 -175.43(15) . . . . ?
C2 N1 C22 C23 -177.03(14) . . . . ?
C2 C1 C10 C11 -147.04(15) . . . . ?
C2 C1 C10 C15 39.1(2) . . . . ?
C2 C1 C16 C17 146.77(15) . . . . ?
C2 C1 C16 C21 -38.9(2) . . . . ?
C2 C3 C4 C5 -101.02(17) . . . . ?
C2 C3 C4 C9 76.34(19) . . . . ?
C3 C4 C5 C6 177.10(16) . . . . ?
C3 C4 C9 C8 -175.88(16) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C5 C4 C9 C8 1.5(2) . . . . ?
C5 C6 C7 C8 1.8(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C4 -1.0(3) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C10 C1 C2 N1 65.46(16) . . . . ?
C10 C1 C2 C3 -175.77(13) . . . . ?
C10 C1 C16 C17 -89.60(17) . . . . ?
C10 C1 C16 C21 84.76(18) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
C16 C1 C2 N1 -174.03(13) . . . . ?
C16 C1 C2 C3 -55.26(17) . . . . ?
C16 C1 C10 C11 88.70(17) . . . . ?
C16 C1 C10 C15 -85.18(18) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C16 C21 C20 -1.0(2) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C16 1.6(3) . . . . ?
C21 C16 C17 C18 -0.1(2) . . . . ?
C22 N1 C2 C1 -118.48(16) . . . . ?
C22 N1 C2 C3 119.94(16) . . . . ?
C22 C23 C24 O2 1.7(2) . . . . ?
C22 C23 C24 C25 -178.29(14) . . . . ?
C22 C23 C28 C27 178.13(14) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C23 C24 C25 C29 178.71(15) . . . . ?
C24 C23 C28 C27 -0.7(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C24 C25 C29 C30 -58.63(19) . . . . ?
C24 C25 C29 C31 62.14(19) . . . . ?
C24 C25 C29 C32 -177.82(14) . . . . ?
C25 C26 C27 C28 0.0(2) . . . . ?
C25 C26 C27 C33 176.97(15) . . . . ?
C26 C25 C29 C30 120.09(16) . . . . ?
C26 C25 C29 C31 -119.13(16) . . . . ?
C26 C25 C29 C32 0.9(2) . . . . ?
C26 C27 C28 C23 0.4(2) . . . . ?
C26 C27 C33 C34 43.3(4) . . . . ?
C26 C27 C33 C35 164.6(2) . . . . ?
C26 C27 C33 C36 -76.1(3) . . . . ?
C26 C27 C33 C34A 18.3(4) . . . . ?
C26 C27 C33 C35A 136.9(5) . . . . ?
C26 C27 C33 C36A -102.5(4) . . . . ?
C28 C23 C24 O2 -179.53(14) . . . . ?
C28 C23 C24 C25 0.5(2) . . . . ?
C28 C27 C33 C34 -139.9(3) . . . . ?
C28 C27 C33 C35 -18.7(3) . . . . ?
C28 C27 C33 C36 100.7(3) . . . . ?
C28 C27 C33 C34A -164.9(4) . . . . ?
C28 C27 C33 C35A -46.3(5) . . . . ?
C28 C27 C33 C36A 74.3(4) . . . . ?
C29 C25 C26 C27 -179.00(15) . . . . ?
C33 C27 C28 C23 -176.44(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.766
