# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 
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data_goebeld180319_0m
_database_code_depnum_ccdc_archive 'CCDC 2018044'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-06-21
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Br N O2'
_chemical_formula_sum            'C20 H20 Br N O2'
_chemical_formula_weight         386.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6343(2)
_cell_length_b                   19.0413(5)
_cell_length_c                   19.4763(5)
_cell_angle_alpha                83.018(2)
_cell_angle_beta                 89.376(2)
_cell_angle_gamma                82.190(2)
_cell_volume                     3513.47(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.638
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.8568.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0411
_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       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            85212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10719
_reflns_number_total             12379
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.710
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.00047(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     886
_refine_ls_number_reflns         12379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.240
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²+27.5138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1510
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C53(H53A,H53B), C73(H73A,H73B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C21(H21), C66(H66), C68(H68),
 C28(H28), C25(H25), C64(H64), C24(H24), C44(H44), C61(H61), C48(H48), C65(H65),
  C26(H26), C46(H46), C45(H45), C41(H41)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C31(H31A,H31B,H31C), C76(H76A,H76B,H76C), C55(H55A,H55B,H55C), C75(H75A,
 H75B,H75C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C56(H56A,H56B,H56C),
 C70(H70A,H70B,H70C), C51(H51A,H51B,H51C), C30(H30A,H30B,H30C), C71(H71A,H71B,
 H71C), C50(H50A,H50B,H50C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O7(H7), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_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
O4 O 0.2876(4) 0.7174(2) 0.6567(2) 0.0200(9) Uani 1 1 d . . . . .
N1 N -0.1056(5) 0.3798(3) 0.7698(3) 0.0191(11) Uani 1 1 d . . . . .
O1 O 0.1126(5) 0.4002(2) 0.6923(2) 0.0248(10) Uani 1 1 d . . . . .
H1 H 0.032392 0.409199 0.709100 0.037 Uiso 1 1 calc R U . . .
C1 C 0.1729(6) 0.2272(3) 0.8010(3) 0.0154(12) Uani 1 1 d . . . . .
H1A H 0.124547 0.196940 0.832399 0.018 Uiso 1 1 calc R U . . .
O2 O -0.0928(4) 0.2787(2) 0.8446(2) 0.0206(9) Uani 1 1 d . . . . .
C2 C 0.1042(6) 0.2926(3) 0.7713(3) 0.0148(12) Uani 1 1 d . . . . .
C3 C 0.1765(6) 0.3369(3) 0.7238(3) 0.0163(12) Uani 1 1 d . . . . .
Br1 Br 0.96117(6) 0.07553(4) 0.75776(3) 0.02451(17) Uani 1 1 d . . . . .
C4 C 0.3168(6) 0.3166(3) 0.7087(3) 0.0158(12) Uani 1 1 d . . . . .
H4 H 0.366084 0.346660 0.677650 0.019 Uiso 1 1 calc R U . . .
C4A C 0.3831(6) 0.2516(3) 0.7401(3) 0.0163(12) Uani 1 1 d . . . . .
C4B C 0.5290(6) 0.2171(3) 0.7356(3) 0.0159(12) Uani 1 1 d . . . . .
C5 C 0.6434(6) 0.2408(3) 0.7004(3) 0.0186(13) Uani 1 1 d . . . . .
H5 H 0.633404 0.285096 0.671391 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7728(6) 0.1983(3) 0.7085(3) 0.0190(13) Uani 1 1 d . . . . .
H6 H 0.853144 0.214022 0.686172 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7839(6) 0.1328(4) 0.7494(3) 0.0191(13) Uani 1 1 d . . . . .
C8 C 0.6709(6) 0.1085(3) 0.7842(3) 0.0176(13) Uani 1 1 d . . . . .
H8 H 0.680538 0.063558 0.812160 0.021 Uiso 1 1 calc R U . . .
C8A C 0.5418(6) 0.1521(3) 0.7770(3) 0.0153(12) Uani 1 1 d . . . . .
C9 C 0.4052(6) 0.1380(3) 0.8128(3) 0.0175(13) Uani 1 1 d . . . . .
C9A C 0.3109(6) 0.2060(3) 0.7851(3) 0.0139(12) Uani 1 1 d . . . . .
C10 C 0.4213(7) 0.1313(4) 0.8924(3) 0.0226(14) Uani 1 1 d . . . . .
H10A H 0.487577 0.088761 0.908147 0.034 Uiso 1 1 calc R U . . .
H10B H 0.330122 0.127010 0.914037 0.034 Uiso 1 1 calc R U . . .
H10C H 0.456596 0.173798 0.905276 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3528(7) 0.0709(3) 0.7912(3) 0.0213(14) Uani 1 1 d . . . . .
H11A H 0.422482 0.029109 0.804492 0.032 Uiso 1 1 calc R U . . .
H11B H 0.338645 0.076920 0.740943 0.032 Uiso 1 1 calc R U . . .
H11C H 0.263978 0.064111 0.814342 0.032 Uiso 1 1 calc R U . . .
C12 C -0.0372(6) 0.3193(3) 0.7927(3) 0.0171(13) Uani 1 1 d . . . . .
C13 C -0.2326(6) 0.3162(3) 0.8543(3) 0.0228(14) Uani 1 1 d . . . . .
H13A H -0.252207 0.318474 0.904048 0.027 Uiso 1 1 calc R U . . .
H13B H -0.304803 0.292074 0.834483 0.027 Uiso 1 1 calc R U . . .
C14 C -0.2298(7) 0.3909(3) 0.8159(3) 0.0215(14) Uani 1 1 d . . . . .
C15 C -0.2006(7) 0.4445(4) 0.8630(4) 0.0295(16) Uani 1 1 d . . . . .
H15A H -0.120185 0.424464 0.892860 0.044 Uiso 1 1 calc R U . . .
H15B H -0.283027 0.455814 0.891633 0.044 Uiso 1 1 calc R U . . .
H15C H -0.179745 0.488203 0.835090 0.044 Uiso 1 1 calc R U . . .
C16 C -0.3644(7) 0.4172(4) 0.7738(4) 0.0274(15) Uani 1 1 d . . . . .
H16A H -0.357378 0.464324 0.748412 0.041 Uiso 1 1 calc R U . . .
H16B H -0.444715 0.420769 0.805086 0.041 Uiso 1 1 calc R U . . .
H16C H -0.377106 0.383488 0.740943 0.041 Uiso 1 1 calc R U . . .
N2 N 0.3263(5) 0.6162(3) 0.7306(3) 0.0172(11) Uani 1 1 d . . . . .
N3 N 0.6047(5) 0.6051(3) 0.5202(3) 0.0185(11) Uani 1 1 d . . . . .
N4 N 1.1635(5) 0.3928(3) -0.0193(3) 0.0196(11) Uani 1 1 d . . . . .
C68A C 0.6752(6) 0.1463(3) 0.0458(3) 0.0148(12) Uani 1 1 d . . . . .
C69 C 0.8258(6) 0.1334(3) 0.0189(3) 0.0148(12) Uani 1 1 d . . . . .
C32 C 0.3639(6) 0.6765(3) 0.7081(3) 0.0145(12) Uani 1 1 d . . . . .
C24A C 0.7448(6) 0.7444(3) 0.7598(3) 0.0159(12) Uani 1 1 d . . . . .
C21 C 0.5232(6) 0.7696(3) 0.6998(3) 0.0140(12) Uani 1 1 d . . . . .
H21 H 0.459288 0.800041 0.668898 0.017 Uiso 1 1 calc R U . . .
C66 C 0.4104(6) 0.1935(3) 0.0928(3) 0.0180(13) Uani 1 1 d . . . . .
H66 H 0.318446 0.208903 0.107911 0.022 Uiso 1 1 calc R U . . .
C49A C 0.2159(6) 0.7927(3) 0.4778(3) 0.0141(12) Uani 1 1 d . . . . .
C29 C 0.7063(6) 0.8596(3) 0.6892(3) 0.0146(12) Uani 1 1 d . . . . .
C68 C 0.5772(6) 0.0990(3) 0.0528(3) 0.0155(12) Uani 1 1 d . . . . .
H68 H 0.598916 0.051229 0.042408 0.019 Uiso 1 1 calc R U . . .
C48A C -0.0086(6) 0.8538(3) 0.4548(3) 0.0149(12) Uani 1 1 d . . . . .
C27 C 1.0831(6) 0.8634(4) 0.7492(3) 0.0195(13) Uani 1 1 d . . . . .
C64B C 0.6425(6) 0.2158(3) 0.0632(3) 0.0141(12) Uani 1 1 d . . . . .
C28 C 0.9567(6) 0.8884(3) 0.7156(3) 0.0177(13) Uani 1 1 d . . . . .
H28 H 0.942661 0.933874 0.688672 0.021 Uiso 1 1 calc R U . . .
C47 C -0.2483(6) 0.8788(4) 0.4231(3) 0.0196(13) Uani 1 1 d . . . . .
C25 C 0.9986(6) 0.7559(3) 0.7981(3) 0.0188(13) Uani 1 1 d . . . . .
H25 H 1.011925 0.711620 0.827186 0.023 Uiso 1 1 calc R U . . .
Br4 Br 0.30291(6) 0.06453(4) 0.08063(3) 0.02262(17) Uani 1 1 d . . . . .
C22 C 0.4908(6) 0.7030(3) 0.7294(3) 0.0152(12) Uani 1 1 d . . . . .
C23 C 0.5845(6) 0.6582(3) 0.7761(3) 0.0151(12) Uani 1 1 d . . . . .
C31 C 0.7140(7) 0.8707(3) 0.6101(3) 0.0218(14) Uani 1 1 d . . . . .
H31A H 0.774078 0.830294 0.593935 0.033 Uiso 1 1 calc R U . . .
H31B H 0.753076 0.914946 0.595248 0.033 Uiso 1 1 calc R U . . .
H31C H 0.619684 0.873963 0.590593 0.033 Uiso 1 1 calc R U . . .
C69A C 0.8716(6) 0.2055(3) 0.0238(3) 0.0161(12) Uani 1 1 d . . . . .
C64 C 0.7827(6) 0.3228(3) 0.0563(3) 0.0168(13) Uani 1 1 d . . . . .
H64 H 0.710087 0.353764 0.074956 0.020 Uiso 1 1 calc R U . . .
C52 C 0.5489(6) 0.6695(3) 0.5208(3) 0.0160(12) Uani 1 1 d . . . . .
C44B C -0.0059(6) 0.7843(3) 0.4378(3) 0.0153(12) Uani 1 1 d . . . . .
C67 C 0.4449(6) 0.1253(3) 0.0758(3) 0.0186(13) Uani 1 1 d . . . . .
C49 C 0.1333(6) 0.8658(3) 0.4819(3) 0.0146(12) Uani 1 1 d . . . . .
C24 C 0.7141(6) 0.6792(3) 0.7902(3) 0.0161(12) Uani 1 1 d . . . . .
H24 H 0.779881 0.648871 0.820245 0.019 Uiso 1 1 calc R U . . .
C44 C 0.1893(6) 0.6759(3) 0.4457(3) 0.0153(12) Uani 1 1 d . . . . .
H44 H 0.133516 0.645095 0.427429 0.018 Uiso 1 1 calc R U . . .
C61 C 0.9979(6) 0.2293(3) 0.0030(3) 0.0143(12) Uani 1 1 d . . . . .
H61 H 1.070652 0.197722 -0.014645 0.017 Uiso 1 1 calc R U . . .
C28A C 0.8517(6) 0.8454(3) 0.7223(3) 0.0159(12) Uani 1 1 d . . . . .
C64A C 0.7647(6) 0.2536(3) 0.0494(3) 0.0158(12) Uani 1 1 d . . . . .
C48 C -0.1302(6) 0.9022(3) 0.4468(3) 0.0165(13) Uani 1 1 d . . . . .
H48 H -0.132096 0.949766 0.457221 0.020 Uiso 1 1 calc R U . . .
C65 C 0.5104(6) 0.2395(3) 0.0878(3) 0.0183(13) Uani 1 1 d . . . . .
H65 H 0.489423 0.286295 0.100736 0.022 Uiso 1 1 calc R U . . .
C43 C 0.3275(6) 0.6518(3) 0.4659(3) 0.0160(12) Uani 1 1 d . . . . .
C26 C 1.1050(6) 0.7979(4) 0.7900(3) 0.0215(14) Uani 1 1 d . . . . .
H26 H 1.192832 0.782004 0.812200 0.026 Uiso 1 1 calc R U . . .
C29A C 0.6491(6) 0.7904(3) 0.7162(3) 0.0150(12) Uani 1 1 d . . . . .
Br2 Br 1.23047(6) 0.92025(4) 0.73845(4) 0.02482(17) Uani 1 1 d . . . . .
C53 C 0.7512(6) 0.6727(3) 0.5743(3) 0.0206(14) Uani 1 1 d . . . . .
H53A H 0.769654 0.675531 0.623759 0.025 Uiso 1 1 calc R U . . .
H53B H 0.828961 0.689970 0.546400 0.025 Uiso 1 1 calc R U . . .
C46 C -0.2498(6) 0.8111(4) 0.4064(3) 0.0228(14) Uani 1 1 d . . . . .
H46 H -0.333293 0.797253 0.389993 0.027 Uiso 1 1 calc R U . . .
C54 C 0.7347(6) 0.5951(3) 0.5623(3) 0.0178(13) Uani 1 1 d . . . . .
C76 C 1.2383(7) 0.4490(4) -0.1291(3) 0.0250(15) Uani 1 1 d . . . . .
H76A H 1.318140 0.456425 -0.159467 0.038 Uiso 1 1 calc R U . . .
H76B H 1.191231 0.495227 -0.118294 0.038 Uiso 1 1 calc R U . . .
H76C H 1.172321 0.424786 -0.152459 0.038 Uiso 1 1 calc R U . . .
C45 C -0.1253(6) 0.7619(3) 0.4139(3) 0.0201(13) Uani 1 1 d . . . . .
H45 H -0.123658 0.714547 0.402868 0.024 Uiso 1 1 calc R U . . .
C55 C 0.7082(7) 0.5497(3) 0.6297(3) 0.0211(14) Uani 1 1 d . . . . .
H55A H 0.681267 0.504221 0.619541 0.032 Uiso 1 1 calc R U . . .
H55B H 0.632488 0.575064 0.654893 0.032 Uiso 1 1 calc R U . . .
H55C H 0.793678 0.540620 0.657965 0.032 Uiso 1 1 calc R U . . .
C73 C 1.3467(6) 0.3264(3) -0.0751(3) 0.0216(14) Uani 1 1 d . . . . .
H73A H 1.368110 0.323665 -0.124570 0.026 Uiso 1 1 calc R U . . .
H73B H 1.433088 0.309124 -0.047535 0.026 Uiso 1 1 calc R U . . .
C75 C 1.3923(7) 0.4391(4) -0.0241(4) 0.0313(17) Uani 1 1 d . . . . .
H75A H 1.475432 0.444765 -0.052521 0.047 Uiso 1 1 calc R U . . .
H75B H 1.420008 0.409200 0.019475 0.047 Uiso 1 1 calc R U . . .
H75C H 1.347141 0.486037 -0.014194 0.047 Uiso 1 1 calc R U . . .
C35 C 0.0884(7) 0.5782(4) 0.7273(4) 0.0264(15) Uani 1 1 d . . . . .
H35A H 0.008903 0.577466 0.696556 0.040 Uiso 1 1 calc R U . . .
H35B H 0.060087 0.610046 0.762366 0.040 Uiso 1 1 calc R U . . .
H35C H 0.118854 0.529863 0.750006 0.040 Uiso 1 1 calc R U . . .
C36 C 0.2685(7) 0.5513(4) 0.6365(4) 0.0257(15) Uani 1 1 d . . . . .
H36A H 0.342912 0.570474 0.608421 0.039 Uiso 1 1 calc R U . . .
H36B H 0.193748 0.542677 0.606170 0.039 Uiso 1 1 calc R U . . .
H36C H 0.306911 0.506393 0.663845 0.039 Uiso 1 1 calc R U . . .
C56 C 0.8566(7) 0.5600(4) 0.5230(4) 0.0297(16) Uani 1 1 d . . . . .
H56A H 0.867040 0.589094 0.478589 0.045 Uiso 1 1 calc R U . . .
H56B H 0.838638 0.512305 0.514656 0.045 Uiso 1 1 calc R U . . .
H56C H 0.942804 0.555978 0.550241 0.045 Uiso 1 1 calc R U . . .
Br3 Br -0.41750(7) 0.94342(4) 0.41532(4) 0.02923(18) Uani 1 1 d . . . . .
O3 O 0.5542(4) 0.5948(2) 0.8065(2) 0.0216(10) Uani 1 1 d . . . . .
H3 H 0.474037 0.588625 0.794042 0.032 Uiso 1 1 calc R U . . .
O8 O 1.2353(4) 0.2843(2) -0.0527(2) 0.0191(9) Uani 1 1 d . . . . .
O7 O 0.9246(5) 0.4148(2) 0.0427(2) 0.0238(10) Uani 1 1 d . . . . .
H7 H 0.998140 0.425300 0.022861 0.036 Uiso 1 1 calc R U . . .
O5 O 0.3786(5) 0.5836(2) 0.4590(2) 0.0232(10) Uani 1 1 d . . . . .
H5A H 0.464638 0.576470 0.468489 0.035 Uiso 1 1 calc R U . . .
O6 O 0.6181(4) 0.7141(2) 0.5524(2) 0.0191(9) Uani 1 1 d . . . . .
C44A C 0.1352(6) 0.7454(3) 0.4529(3) 0.0145(12) Uani 1 1 d . . . . .
C72 C 1.1407(6) 0.3286(3) -0.0202(3) 0.0148(12) Uani 1 1 d . . . . .
C62 C 1.0167(6) 0.2996(3) 0.0082(3) 0.0147(12) Uani 1 1 d . . . . .
C70 C 0.9133(6) 0.0726(3) 0.0642(3) 0.0207(14) Uani 1 1 d . . . . .
H70A H 0.914784 0.084224 0.111855 0.031 Uiso 1 1 calc R U . . .
H70B H 1.009237 0.066164 0.046532 0.031 Uiso 1 1 calc R U . . .
H70C H 0.872132 0.028397 0.063388 0.031 Uiso 1 1 calc R U . . .
C63 C 0.9099(6) 0.3472(3) 0.0356(3) 0.0169(13) Uani 1 1 d . . . . .
C51 C 0.1937(6) 0.9261(3) 0.4372(3) 0.0197(13) Uani 1 1 d . . . . .
H51A H 0.208223 0.913496 0.390054 0.030 Uiso 1 1 calc R U . . .
H51B H 0.283419 0.932974 0.456762 0.030 Uiso 1 1 calc R U . . .
H51C H 0.128137 0.970315 0.436024 0.030 Uiso 1 1 calc R U . . .
C24B C 0.8722(6) 0.7784(3) 0.7638(3) 0.0153(12) Uani 1 1 d . . . . .
C41 C 0.3535(6) 0.7690(3) 0.4980(3) 0.0160(12) Uani 1 1 d . . . . .
H41 H 0.409389 0.800644 0.515027 0.019 Uiso 1 1 calc R U . . .
C30 C 0.6209(6) 0.9235(3) 0.7167(3) 0.0205(13) Uani 1 1 d . . . . .
H30A H 0.524492 0.929053 0.699306 0.031 Uiso 1 1 calc R U . . .
H30B H 0.662739 0.966835 0.701243 0.031 Uiso 1 1 calc R U . . .
H30C H 0.620490 0.915856 0.767422 0.031 Uiso 1 1 calc R U . . .
C74 C 1.2897(6) 0.4035(3) -0.0630(3) 0.0196(13) Uani 1 1 d . . . . .
C33 C 0.1685(6) 0.6804(3) 0.6467(3) 0.0224(14) Uani 1 1 d . . . . .
H33A H 0.152427 0.678317 0.596918 0.027 Uiso 1 1 calc R U . . .
H33B H 0.082508 0.704633 0.666498 0.027 Uiso 1 1 calc R U . . .
C34 C 0.2090(6) 0.6052(3) 0.6851(3) 0.0182(13) Uani 1 1 d . . . . .
C71 C 0.8259(7) 0.1171(3) -0.0563(3) 0.0226(14) Uani 1 1 d . . . . .
H71A H 0.786850 0.072536 -0.058500 0.034 Uiso 1 1 calc R U . . .
H71B H 0.922183 0.112169 -0.073597 0.034 Uiso 1 1 calc R U . . .
H71C H 0.768798 0.156256 -0.084731 0.034 Uiso 1 1 calc R U . . .
C50 C 0.1212(6) 0.8821(3) 0.5574(3) 0.0189(13) Uani 1 1 d . . . . .
H50A H 0.213698 0.887977 0.574548 0.028 Uiso 1 1 calc R U . . .
H50B H 0.085583 0.842491 0.586025 0.028 Uiso 1 1 calc R U . . .
H50C H 0.056609 0.926161 0.559829 0.028 Uiso 1 1 calc R U . . .
C42 C 0.4087(6) 0.6987(3) 0.4933(3) 0.0156(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C32 1.349(7) . ?
O4 C33 1.452(7) . ?
N1 C12 1.280(8) . ?
N1 C14 1.495(8) . ?
O1 H1 0.8400 . ?
O1 C3 1.355(7) . ?
C1 H1A 0.9500 . ?
C1 C2 1.390(8) . ?
C1 C9A 1.380(8) . ?
O2 C12 1.348(7) . ?
O2 C13 1.457(7) . ?
C2 C3 1.417(8) . ?
C2 C12 1.462(8) . ?
C3 C4 1.393(8) . ?
Br1 C7 1.894(6) . ?
C4 H4 0.9500 . ?
C4 C4A 1.388(8) . ?
C4A C4B 1.474(8) . ?
C4A C9A 1.403(8) . ?
C4B C5 1.391(8) . ?
C4B C8A 1.384(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(9) . ?
C7 C8 1.379(9) . ?
C8 H8 0.9500 . ?
C8 C8A 1.397(8) . ?
C8A C9 1.524(8) . ?
C9 C9A 1.522(8) . ?
C9 C10 1.547(8) . ?
C9 C11 1.540(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.528(9) . ?
C14 C15 1.508(10) . ?
C14 C16 1.534(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 C32 1.276(8) . ?
N2 C34 1.496(7) . ?
N3 C52 1.270(8) . ?
N3 C54 1.483(8) . ?
N4 C72 1.273(8) . ?
N4 C74 1.498(8) . ?
C68A C69 1.535(8) . ?
C68A C68 1.387(8) . ?
C68A C64B 1.399(8) . ?
C69 C69A 1.513(8) . ?
C69 C70 1.527(8) . ?
C69 C71 1.533(8) . ?
C32 C22 1.467(8) . ?
C24A C24 1.378(8) . ?
C24A C29A 1.398(8) . ?
C24A C24B 1.471(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.402(8) . ?
C21 C29A 1.378(8) . ?
C66 H66 0.9500 . ?
C66 C67 1.375(9) . ?
C66 C65 1.383(9) . ?
C49A C49 1.517(8) . ?
C49A C44A 1.399(8) . ?
C49A C41 1.386(8) . ?
C29 C31 1.530(8) . ?
C29 C28A 1.525(8) . ?
C29 C29A 1.529(8) . ?
C29 C30 1.526(8) . ?
C68 H68 0.9500 . ?
C68 C67 1.395(8) . ?
C48A C44B 1.398(9) . ?
C48A C49 1.527(8) . ?
C48A C48 1.387(8) . ?
C27 C28 1.386(8) . ?
C27 C26 1.386(9) . ?
C27 Br2 1.895(6) . ?
C64B C64A 1.468(8) . ?
C64B C65 1.391(8) . ?
C28 H28 0.9500 . ?
C28 C28A 1.381(8) . ?
C47 C48 1.381(9) . ?
C47 C46 1.370(10) . ?
C47 Br3 1.899(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(9) . ?
C25 C24B 1.385(8) . ?
Br4 C67 1.903(6) . ?
C22 C23 1.412(8) . ?
C23 C24 1.402(8) . ?
C23 O3 1.346(7) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C69A C61 1.394(8) . ?
C69A C64A 1.411(8) . ?
C64 H64 0.9500 . ?
C64 C64A 1.374(9) . ?
C64 C63 1.407(8) . ?
C52 O6 1.354(7) . ?
C52 C42 1.470(8) . ?
C44B C45 1.384(8) . ?
C44B C44A 1.471(8) . ?
C49 C51 1.530(8) . ?
C49 C50 1.540(8) . ?
C24 H24 0.9500 . ?
C44 H44 0.9500 . ?
C44 C43 1.392(8) . ?
C44 C44A 1.377(8) . ?
C61 H61 0.9500 . ?
C61 C62 1.390(8) . ?
C28A C24B 1.415(8) . ?
C48 H48 0.9500 . ?
C65 H65 0.9500 . ?
C43 O5 1.348(7) . ?
C43 C42 1.417(8) . ?
C26 H26 0.9500 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C54 1.553(9) . ?
C53 O6 1.451(7) . ?
C46 H46 0.9500 . ?
C46 C45 1.415(9) . ?
C54 C55 1.520(9) . ?
C54 C56 1.518(9) . ?
C76 H76A 0.9800 . ?
C76 H76B 0.9800 . ?
C76 H76C 0.9800 . ?
C76 C74 1.510(9) . ?
C45 H45 0.9500 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C73 O8 1.458(7) . ?
C73 C74 1.540(9) . ?
C75 H75A 0.9800 . ?
C75 H75B 0.9800 . ?
C75 H75C 0.9800 . ?
C75 C74 1.528(9) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 C34 1.525(8) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36 C34 1.529(9) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
O3 H3 0.8400 . ?
O8 C72 1.361(7) . ?
O7 H7 0.8400 . ?
O7 C63 1.338(7) . ?
O5 H5A 0.8400 . ?
C72 C62 1.459(8) . ?
C62 C63 1.420(8) . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C41 H41 0.9500 . ?
C41 C42 1.386(8) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.535(9) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 O4 C33 105.4(4) . . ?
C12 N1 C14 106.4(5) . . ?
C3 O1 H1 109.5 . . ?
C2 C1 H1A 119.9 . . ?
C9A C1 H1A 119.9 . . ?
C9A C1 C2 120.2(5) . . ?
C12 O2 C13 104.9(5) . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 C12 121.1(5) . . ?
C3 C2 C12 119.2(5) . . ?
O1 C3 C2 121.5(5) . . ?
O1 C3 C4 118.0(5) . . ?
C4 C3 C2 120.6(5) . . ?
C3 C4 H4 120.7 . . ?
C4A C4 C3 118.5(5) . . ?
C4A C4 H4 120.7 . . ?
C4 C4A C4B 130.8(5) . . ?
C4 C4A C9A 121.3(5) . . ?
C9A C4A C4B 107.9(5) . . ?
C5 C4B C4A 130.8(6) . . ?
C8A C4B C4A 108.0(5) . . ?
C8A C4B C5 121.2(6) . . ?
C4B C5 H5 120.7 . . ?
C6 C5 C4B 118.6(6) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 Br1 118.4(4) . . ?
C8 C7 Br1 119.3(5) . . ?
C8 C7 C6 122.3(6) . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C8A 117.8(6) . . ?
C8A C8 H8 121.1 . . ?
C4B C8A C8 120.5(5) . . ?
C4B C8A C9 112.5(5) . . ?
C8 C8A C9 127.0(5) . . ?
C8A C9 C10 111.0(5) . . ?
C8A C9 C11 111.7(5) . . ?
C9A C9 C8A 100.0(5) . . ?
C9A C9 C10 111.5(5) . . ?
C9A C9 C11 112.0(5) . . ?
C11 C9 C10 110.4(5) . . ?
C1 C9A C4A 119.8(5) . . ?
C1 C9A C9 128.5(5) . . ?
C4A C9A C9 111.7(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 O2 118.5(5) . . ?
N1 C12 C2 125.0(6) . . ?
O2 C12 C2 116.2(5) . . ?
O2 C13 H13A 110.8 . . ?
O2 C13 H13B 110.8 . . ?
O2 C13 C14 104.5(5) . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
N1 C14 C13 102.3(5) . . ?
N1 C14 C15 107.3(5) . . ?
N1 C14 C16 111.3(5) . . ?
C13 C14 C16 111.7(5) . . ?
C15 C14 C13 112.9(6) . . ?
C15 C14 C16 110.9(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C32 N2 C34 107.1(5) . . ?
C52 N3 C54 107.2(5) . . ?
C72 N4 C74 107.7(5) . . ?
C68 C68A C69 127.8(5) . . ?
C68 C68A C64B 121.0(5) . . ?
C64B C68A C69 111.2(5) . . ?
C69A C69 C68A 100.4(5) . . ?
C69A C69 C70 113.1(5) . . ?
C69A C69 C71 111.2(5) . . ?
C70 C69 C68A 111.2(5) . . ?
C70 C69 C71 110.2(5) . . ?
C71 C69 C68A 110.5(5) . . ?
O4 C32 C22 116.4(5) . . ?
N2 C32 O4 118.0(5) . . ?
N2 C32 C22 125.4(5) . . ?
C24 C24A C29A 121.6(5) . . ?
C24 C24A C24B 130.3(5) . . ?
C29A C24A C24B 108.1(5) . . ?
C22 C21 H21 120.5 . . ?
C29A C21 H21 120.5 . . ?
C29A C21 C22 119.0(5) . . ?
C67 C66 H66 120.2 . . ?
C67 C66 C65 119.6(5) . . ?
C65 C66 H66 120.2 . . ?
C44A C49A C49 112.5(5) . . ?
C41 C49A C49 127.9(5) . . ?
C41 C49A C44A 119.6(6) . . ?
C28A C29 C31 111.8(5) . . ?
C28A C29 C29A 100.5(5) . . ?
C28A C29 C30 110.0(5) . . ?
C29A C29 C31 112.3(5) . . ?
C30 C29 C31 111.1(5) . . ?
C30 C29 C29A 110.8(5) . . ?
C68A C68 H68 121.8 . . ?
C68A C68 C67 116.3(5) . . ?
C67 C68 H68 121.8 . . ?
C44B C48A C49 111.6(5) . . ?
C48 C48A C44B 120.8(5) . . ?
C48 C48A C49 127.6(5) . . ?
C28 C27 Br2 118.9(5) . . ?
C26 C27 C28 122.0(6) . . ?
C26 C27 Br2 119.1(4) . . ?
C68A C64B C64A 108.8(5) . . ?
C65 C64B C68A 121.0(5) . . ?
C65 C64B C64A 130.1(6) . . ?
C27 C28 H28 120.9 . . ?
C28A C28 C27 118.2(6) . . ?
C28A C28 H28 120.9 . . ?
C48 C47 Br3 118.1(5) . . ?
C46 C47 C48 123.1(6) . . ?
C46 C47 Br3 118.7(5) . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24B 119.7(6) . . ?
C24B C25 H25 120.1 . . ?
C21 C22 C32 120.3(5) . . ?
C21 C22 C23 120.7(5) . . ?
C23 C22 C32 118.9(5) . . ?
C24 C23 C22 119.4(5) . . ?
O3 C23 C22 121.8(5) . . ?
O3 C23 C24 118.8(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 . . ?
C61 C69A C69 128.5(5) . . ?
C61 C69A C64A 119.1(5) . . ?
C64A C69A C69 112.3(5) . . ?
C64A C64 H64 120.4 . . ?
C64A C64 C63 119.2(5) . . ?
C63 C64 H64 120.4 . . ?
N3 C52 O6 118.8(5) . . ?
N3 C52 C42 124.5(5) . . ?
O6 C52 C42 116.6(5) . . ?
C48A C44B C44A 108.4(5) . . ?
C45 C44B C48A 120.8(6) . . ?
C45 C44B C44A 130.8(6) . . ?
C66 C67 C68 123.5(5) . . ?
C66 C67 Br4 118.4(4) . . ?
C68 C67 Br4 118.0(5) . . ?
C49A C49 C48A 100.0(5) . . ?
C49A C49 C51 113.4(5) . . ?
C49A C49 C50 110.7(5) . . ?
C48A C49 C51 111.9(5) . . ?
C48A C49 C50 110.5(5) . . ?
C51 C49 C50 110.0(5) . . ?
C24A C24 C23 119.0(5) . . ?
C24A C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C43 C44 H44 120.7 . . ?
C44A C44 H44 120.7 . . ?
C44A C44 C43 118.7(5) . . ?
C69A C61 H61 120.2 . . ?
C62 C61 C69A 119.6(5) . . ?
C62 C61 H61 120.2 . . ?
C28 C28A C29 128.2(5) . . ?
C28 C28A C24B 120.6(5) . . ?
C24B C28A C29 111.2(5) . . ?
C69A C64A C64B 107.4(5) . . ?
C64 C64A C64B 130.6(6) . . ?
C64 C64A C69A 122.0(6) . . ?
C48A C48 H48 121.2 . . ?
C47 C48 C48A 117.6(6) . . ?
C47 C48 H48 121.2 . . ?
C66 C65 C64B 118.5(6) . . ?
C66 C65 H65 120.8 . . ?
C64B C65 H65 120.8 . . ?
C44 C43 C42 119.7(5) . . ?
O5 C43 C44 118.0(5) . . ?
O5 C43 C42 122.3(5) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 C27 119.7(6) . . ?
C25 C26 H26 120.1 . . ?
C24A C29A C29 112.0(5) . . ?
C21 C29A C24A 120.2(6) . . ?
C21 C29A C29 127.7(5) . . ?
H53A C53 H53B 108.9 . . ?
C54 C53 H53A 110.9 . . ?
C54 C53 H53B 110.9 . . ?
O6 C53 H53A 110.9 . . ?
O6 C53 H53B 110.9 . . ?
O6 C53 C54 104.4(5) . . ?
C47 C46 H46 120.4 . . ?
C47 C46 C45 119.2(6) . . ?
C45 C46 H46 120.4 . . ?
N3 C54 C53 102.6(5) . . ?
N3 C54 C55 107.5(5) . . ?
N3 C54 C56 110.2(5) . . ?
C55 C54 C53 111.5(5) . . ?
C56 C54 C53 112.8(5) . . ?
C56 C54 C55 111.6(5) . . ?
H76A C76 H76B 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
C74 C76 H76A 109.5 . . ?
C74 C76 H76B 109.5 . . ?
C74 C76 H76C 109.5 . . ?
C44B C45 C46 118.5(6) . . ?
C44B C45 H45 120.8 . . ?
C46 C45 H45 120.8 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
H73A C73 H73B 108.8 . . ?
O8 C73 H73A 110.7 . . ?
O8 C73 H73B 110.7 . . ?
O8 C73 C74 105.2(5) . . ?
C74 C73 H73A 110.7 . . ?
C74 C73 H73B 110.7 . . ?
H75A C75 H75B 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C74 C75 H75A 109.5 . . ?
C74 C75 H75B 109.5 . . ?
C74 C75 H75C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C23 O3 H3 109.5 . . ?
C72 O8 C73 105.3(4) . . ?
C63 O7 H7 109.5 . . ?
C43 O5 H5A 109.5 . . ?
C52 O6 C53 105.4(5) . . ?
C49A C44A C44B 107.5(5) . . ?
C44 C44A C49A 122.0(5) . . ?
C44 C44A C44B 130.5(5) . . ?
N4 C72 O8 118.0(5) . . ?
N4 C72 C62 124.9(5) . . ?
O8 C72 C62 117.1(5) . . ?
C61 C62 C72 121.1(5) . . ?
C61 C62 C63 120.9(5) . . ?
C63 C62 C72 117.8(5) . . ?
C69 C70 H70A 109.5 . . ?
C69 C70 H70B 109.5 . . ?
C69 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C64 C63 C62 119.1(5) . . ?
O7 C63 C64 118.0(5) . . ?
O7 C63 C62 122.8(5) . . ?
C49 C51 H51A 109.5 . . ?
C49 C51 H51B 109.5 . . ?
C49 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C25 C24B C24A 132.0(6) . . ?
C25 C24B C28A 119.8(6) . . ?
C28A C24B C24A 108.3(5) . . ?
C49A C41 H41 120.3 . . ?
C42 C41 C49A 119.3(5) . . ?
C42 C41 H41 120.3 . . ?
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 . . ?
N4 C74 C76 107.1(5) . . ?
N4 C74 C73 102.0(5) . . ?
N4 C74 C75 110.0(5) . . ?
C76 C74 C73 112.2(5) . . ?
C76 C74 C75 111.7(6) . . ?
C75 C74 C73 113.2(5) . . ?
O4 C33 H33A 110.8 . . ?
O4 C33 H33B 110.8 . . ?
O4 C33 C34 104.6(5) . . ?
H33A C33 H33B 108.9 . . ?
C34 C33 H33A 110.8 . . ?
C34 C33 H33B 110.8 . . ?
N2 C34 C35 111.6(5) . . ?
N2 C34 C36 107.5(5) . . ?
N2 C34 C33 101.8(5) . . ?
C35 C34 C36 110.6(5) . . ?
C35 C34 C33 112.6(5) . . ?
C36 C34 C33 112.3(5) . . ?
C69 C71 H71A 109.5 . . ?
C69 C71 H71B 109.5 . . ?
C69 C71 H71C 109.5 . . ?
H71A C71 H71B 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C43 C42 C52 118.3(5) . . ?
C41 C42 C52 120.9(5) . . ?
C41 C42 C43 120.7(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
O4 C32 C22 C21 3.8(8) . . . . ?
O4 C32 C22 C23 -171.5(5) . . . . ?
O4 C33 C34 N2 17.3(6) . . . . ?
O4 C33 C34 C35 136.9(5) . . . . ?
O4 C33 C34 C36 -97.4(6) . . . . ?
O1 C3 C4 C4A -179.4(5) . . . . ?
C1 C2 C3 O1 178.3(5) . . . . ?
C1 C2 C3 C4 -2.5(9) . . . . ?
C1 C2 C12 N1 177.4(6) . . . . ?
C1 C2 C12 O2 3.2(8) . . . . ?
O2 C13 C14 N1 17.9(6) . . . . ?
O2 C13 C14 C15 -97.0(6) . . . . ?
O2 C13 C14 C16 137.1(5) . . . . ?
C2 C1 C9A C4A 1.6(9) . . . . ?
C2 C1 C9A C9 178.6(6) . . . . ?
C2 C3 C4 C4A 1.4(9) . . . . ?
C3 C2 C12 N1 2.7(9) . . . . ?
C3 C2 C12 O2 -171.5(5) . . . . ?
C3 C4 C4A C4B -178.4(6) . . . . ?
C3 C4 C4A C9A 1.2(9) . . . . ?
Br1 C7 C8 C8A 179.9(4) . . . . ?
C4 C4A C4B C5 2.3(11) . . . . ?
C4 C4A C4B C8A -179.9(6) . . . . ?
C4 C4A C9A C1 -2.7(9) . . . . ?
C4 C4A C9A C9 179.8(5) . . . . ?
C4A C4B C5 C6 176.4(6) . . . . ?
C4A C4B C8A C8 -178.2(5) . . . . ?
C4A C4B C8A C9 -0.2(7) . . . . ?
C4B C4A C9A C1 177.0(5) . . . . ?
C4B C4A C9A C9 -0.5(7) . . . . ?
C4B C5 C6 C7 2.0(9) . . . . ?
C4B C8A C9 C9A -0.1(6) . . . . ?
C4B C8A C9 C10 -117.8(6) . . . . ?
C4B C8A C9 C11 118.5(6) . . . . ?
C5 C4B C8A C8 -0.1(9) . . . . ?
C5 C4B C8A C9 177.9(5) . . . . ?
C5 C6 C7 Br1 178.8(5) . . . . ?
C5 C6 C7 C8 -1.6(9) . . . . ?
C6 C7 C8 C8A 0.3(9) . . . . ?
C7 C8 C8A C4B 0.6(9) . . . . ?
C7 C8 C8A C9 -177.1(6) . . . . ?
C8 C8A C9 C9A 177.8(6) . . . . ?
C8 C8A C9 C10 60.0(8) . . . . ?
C8 C8A C9 C11 -63.6(8) . . . . ?
C8A C4B C5 C6 -1.2(9) . . . . ?
C8A C9 C9A C1 -176.9(6) . . . . ?
C8A C9 C9A C4A 0.4(6) . . . . ?
C9A C1 C2 C3 1.0(9) . . . . ?
C9A C1 C2 C12 -173.7(5) . . . . ?
C9A C4A C4B C5 -177.4(6) . . . . ?
C9A C4A C4B C8A 0.5(7) . . . . ?
C10 C9 C9A C1 -59.5(8) . . . . ?
C10 C9 C9A C4A 117.7(6) . . . . ?
C11 C9 C9A C1 64.7(8) . . . . ?
C11 C9 C9A C4A -118.1(6) . . . . ?
C12 N1 C14 C13 -14.6(6) . . . . ?
C12 N1 C14 C15 104.4(6) . . . . ?
C12 N1 C14 C16 -134.0(6) . . . . ?
C12 O2 C13 C14 -15.3(6) . . . . ?
C12 C2 C3 O1 -6.9(9) . . . . ?
C12 C2 C3 C4 172.3(5) . . . . ?
C13 O2 C12 N1 6.5(7) . . . . ?
C13 O2 C12 C2 -178.9(5) . . . . ?
C14 N1 C12 O2 5.7(7) . . . . ?
C14 N1 C12 C2 -168.4(6) . . . . ?
N2 C32 C22 C21 178.5(6) . . . . ?
N2 C32 C22 C23 3.1(9) . . . . ?
N3 C52 O6 C53 3.9(7) . . . . ?
N3 C52 C42 C43 1.9(9) . . . . ?
N3 C52 C42 C41 177.8(6) . . . . ?
N4 C72 C62 C61 177.8(6) . . . . ?
N4 C72 C62 C63 3.5(9) . . . . ?
C68A C69 C69A C61 -176.1(6) . . . . ?
C68A C69 C69A C64A -0.2(6) . . . . ?
C68A C68 C67 C66 -1.5(9) . . . . ?
C68A C68 C67 Br4 176.0(4) . . . . ?
C68A C64B C64A C69A -0.4(7) . . . . ?
C68A C64B C64A C64 178.1(6) . . . . ?
C68A C64B C65 C66 -1.7(9) . . . . ?
C69 C68A C68 C67 -177.3(6) . . . . ?
C69 C68A C64B C64A 0.3(7) . . . . ?
C69 C68A C64B C65 179.0(5) . . . . ?
C69 C69A C61 C62 176.1(6) . . . . ?
C69 C69A C64A C64B 0.4(7) . . . . ?
C69 C69A C64A C64 -178.3(5) . . . . ?
C32 O4 C33 C34 -14.6(6) . . . . ?
C32 N2 C34 C35 -134.7(6) . . . . ?
C32 N2 C34 C36 103.9(6) . . . . ?
C32 N2 C34 C33 -14.3(6) . . . . ?
C32 C22 C23 C24 172.1(5) . . . . ?
C32 C22 C23 O3 -6.4(9) . . . . ?
C21 C22 C23 C24 -3.2(9) . . . . ?
C21 C22 C23 O3 178.3(5) . . . . ?
C49A C41 C42 C52 -173.7(5) . . . . ?
C49A C41 C42 C43 2.1(9) . . . . ?
C29 C28A C24B C24A 0.9(7) . . . . ?
C29 C28A C24B C25 179.8(5) . . . . ?
C68 C68A C69 C69A 179.1(6) . . . . ?
C68 C68A C69 C70 -61.0(8) . . . . ?
C68 C68A C69 C71 61.7(8) . . . . ?
C68 C68A C64B C64A -179.0(5) . . . . ?
C68 C68A C64B C65 -0.3(9) . . . . ?
C48A C44B C45 C46 0.7(9) . . . . ?
C48A C44B C44A C49A -0.9(6) . . . . ?
C48A C44B C44A C44 179.3(6) . . . . ?
C27 C28 C28A C29 -178.1(6) . . . . ?
C27 C28 C28A C24B 1.6(9) . . . . ?
C64B C68A C69 C69A -0.1(6) . . . . ?
C64B C68A C69 C70 119.8(6) . . . . ?
C64B C68A C69 C71 -117.5(6) . . . . ?
C64B C68A C68 C67 1.9(8) . . . . ?
C28 C27 C26 C25 -0.3(9) . . . . ?
C28 C28A C24B C24A -178.8(5) . . . . ?
C28 C28A C24B C25 0.1(9) . . . . ?
C47 C46 C45 C44B -0.2(9) . . . . ?
C22 C21 C29A C24A 2.2(8) . . . . ?
C22 C21 C29A C29 178.9(5) . . . . ?
C22 C23 C24 C24A 2.3(9) . . . . ?
C31 C29 C28A C28 58.9(8) . . . . ?
C31 C29 C28A C24B -120.8(5) . . . . ?
C31 C29 C29A C24A 120.6(6) . . . . ?
C31 C29 C29A C21 -56.4(8) . . . . ?
C69A C61 C62 C72 -173.0(5) . . . . ?
C69A C61 C62 C63 1.1(9) . . . . ?
C52 N3 C54 C53 -10.3(6) . . . . ?
C52 N3 C54 C55 107.4(6) . . . . ?
C52 N3 C54 C56 -130.7(6) . . . . ?
C44B C48A C49 C49A -0.1(6) . . . . ?
C44B C48A C49 C51 120.2(6) . . . . ?
C44B C48A C49 C50 -116.8(6) . . . . ?
C44B C48A C48 C47 1.5(9) . . . . ?
C67 C66 C65 C64B 2.1(9) . . . . ?
C49 C49A C44A C44B 0.9(7) . . . . ?
C49 C49A C44A C44 -179.3(5) . . . . ?
C49 C49A C41 C42 176.8(5) . . . . ?
C49 C48A C44B C45 178.3(5) . . . . ?
C49 C48A C44B C44A 0.6(7) . . . . ?
C49 C48A C48 C47 -178.1(6) . . . . ?
C24 C24A C29A C21 -3.1(9) . . . . ?
C24 C24A C29A C29 179.7(5) . . . . ?
C24 C24A C24B C25 0.5(11) . . . . ?
C24 C24A C24B C28A 179.2(6) . . . . ?
C44 C43 C42 C52 173.6(5) . . . . ?
C44 C43 C42 C41 -2.3(9) . . . . ?
C61 C69A C64A C64B 176.7(5) . . . . ?
C61 C69A C64A C64 -2.0(9) . . . . ?
C61 C62 C63 C64 -1.2(9) . . . . ?
C61 C62 C63 O7 178.7(6) . . . . ?
C28A C29 C29A C24A 1.7(6) . . . . ?
C28A C29 C29A C21 -175.3(6) . . . . ?
C64A C64B C65 C66 176.6(6) . . . . ?
C64A C69A C61 C62 0.5(9) . . . . ?
C64A C64 C63 O7 179.8(5) . . . . ?
C64A C64 C63 C62 -0.2(9) . . . . ?
C48 C48A C44B C45 -1.3(9) . . . . ?
C48 C48A C44B C44A -179.0(5) . . . . ?
C48 C48A C49 C49A 179.4(6) . . . . ?
C48 C48A C49 C51 -60.2(8) . . . . ?
C48 C48A C49 C50 62.7(8) . . . . ?
C48 C47 C46 C45 0.4(9) . . . . ?
C65 C66 C67 C68 -0.5(9) . . . . ?
C65 C66 C67 Br4 -178.0(5) . . . . ?
C65 C64B C64A C69A -178.9(6) . . . . ?
C65 C64B C64A C64 -0.4(11) . . . . ?
C43 C44 C44A C49A 1.9(9) . . . . ?
C43 C44 C44A C44B -178.3(6) . . . . ?
C26 C27 C28 C28A -1.5(9) . . . . ?
C26 C25 C24B C24A 176.7(6) . . . . ?
C26 C25 C24B C28A -1.9(9) . . . . ?
C29A C24A C24 C23 0.8(9) . . . . ?
C29A C24A C24B C25 -178.5(6) . . . . ?
C29A C24A C24B C28A 0.2(7) . . . . ?
C29A C21 C22 C32 -174.3(5) . . . . ?
C29A C21 C22 C23 1.0(9) . . . . ?
C29A C29 C28A C28 178.2(6) . . . . ?
C29A C29 C28A C24B -1.5(6) . . . . ?
Br2 C27 C28 C28A 178.1(4) . . . . ?
Br2 C27 C26 C25 -179.9(5) . . . . ?
C46 C47 C48 C48A -1.0(9) . . . . ?
C54 N3 C52 O6 4.6(7) . . . . ?
C54 N3 C52 C42 -171.2(5) . . . . ?
C54 C53 O6 C52 -10.0(6) . . . . ?
C45 C44B C44A C49A -178.3(6) . . . . ?
C45 C44B C44A C44 1.9(11) . . . . ?
C73 O8 C72 N4 3.3(7) . . . . ?
C73 O8 C72 C62 -179.7(5) . . . . ?
Br3 C47 C48 C48A 177.6(4) . . . . ?
Br3 C47 C46 C45 -178.2(5) . . . . ?
O3 C23 C24 C24A -179.2(5) . . . . ?
O8 C73 C74 N4 12.7(6) . . . . ?
O8 C73 C74 C76 -101.6(6) . . . . ?
O8 C73 C74 C75 130.9(6) . . . . ?
O8 C72 C62 C61 1.0(8) . . . . ?
O8 C72 C62 C63 -173.3(5) . . . . ?
O5 C43 C42 C52 -5.6(8) . . . . ?
O5 C43 C42 C41 178.5(5) . . . . ?
O6 C52 C42 C43 -174.0(5) . . . . ?
O6 C52 C42 C41 1.9(8) . . . . ?
O6 C53 C54 N3 12.2(6) . . . . ?
O6 C53 C54 C55 -102.6(6) . . . . ?
O6 C53 C54 C56 130.8(5) . . . . ?
C44A C49A C49 C48A -0.5(6) . . . . ?
C44A C49A C49 C51 -119.7(6) . . . . ?
C44A C49A C49 C50 116.1(5) . . . . ?
C44A C49A C41 C42 0.0(8) . . . . ?
C44A C44B C45 C46 177.7(6) . . . . ?
C44A C44 C43 O5 179.5(5) . . . . ?
C44A C44 C43 C42 0.3(8) . . . . ?
C72 N4 C74 C76 106.8(6) . . . . ?
C72 N4 C74 C73 -11.2(6) . . . . ?
C72 N4 C74 C75 -131.6(6) . . . . ?
C72 C62 C63 C64 173.1(5) . . . . ?
C72 C62 C63 O7 -7.0(9) . . . . ?
C70 C69 C69A C61 65.4(8) . . . . ?
C70 C69 C69A C64A -118.7(6) . . . . ?
C63 C64 C64A C64B -176.5(6) . . . . ?
C63 C64 C64A C69A 1.9(9) . . . . ?
C24B C24A C24 C23 -178.0(6) . . . . ?
C24B C24A C29A C21 175.9(5) . . . . ?
C24B C24A C29A C29 -1.2(7) . . . . ?
C24B C25 C26 C27 2.0(9) . . . . ?
C41 C49A C49 C48A -177.4(6) . . . . ?
C41 C49A C49 C51 63.3(8) . . . . ?
C41 C49A C49 C50 -60.8(8) . . . . ?
C41 C49A C44A C44B 178.1(5) . . . . ?
C41 C49A C44A C44 -2.1(9) . . . . ?
C30 C29 C28A C28 -65.0(8) . . . . ?
C30 C29 C28A C24B 115.3(6) . . . . ?
C30 C29 C29A C24A -114.5(6) . . . . ?
C30 C29 C29A C21 68.6(8) . . . . ?
C74 N4 C72 O8 5.5(7) . . . . ?
C74 N4 C72 C62 -171.3(5) . . . . ?
C74 C73 O8 C72 -10.2(6) . . . . ?
C33 O4 C32 N2 6.0(7) . . . . ?
C33 O4 C32 C22 -178.9(5) . . . . ?
C34 N2 C32 O4 5.9(7) . . . . ?
C34 N2 C32 C22 -168.6(6) . . . . ?
C71 C69 C69A C61 -59.2(8) . . . . ?
C71 C69 C69A C64A 116.7(6) . . . . ?
C42 C52 O6 C53 -180.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld200519_0m
_database_code_depnum_ccdc_archive 'CCDC 2018051'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-06-21
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 Br N O2, C H Cl3'
_chemical_formula_sum            'C27 H19 Br Cl3 N O2'
_chemical_formula_weight         575.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   12.6799(6)
_cell_length_b                   6.6733(3)
_cell_length_c                   15.0742(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.160(2)
_cell_angle_gamma                90
_cell_volume                     1204.87(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.08
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1123 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8179.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33721
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2906
_reflns_number_total             3230
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.740
_refine_diff_density_min         -1.604
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.118
_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)+(0.0581P)²+2.3567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained planarity
 H1, O1, C3, C2, C12, N1
 with sigma of 0.1
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.04955(3) 0.750000 -0.08785(2) 0.02219(13) Uani 1 2 d S T P . .
O1 O 0.65007(19) 0.750000 0.49108(17) 0.0169(5) Uani 1 2 d S T P . .
H1 H 0.665790 0.750000 0.549726 0.025 Uiso 1 2 calc R U P . .
O2 O 0.4405(2) 0.750000 0.65590(16) 0.0168(5) Uani 1 2 d S T P . .
N1 N 0.6167(2) 0.750000 0.6524(2) 0.0138(6) Uani 1 2 d S T P . .
C1 C 0.3477(3) 0.750000 0.4574(2) 0.0126(6) Uani 1 2 d S T P . .
H1A H 0.298185 0.750000 0.493052 0.015 Uiso 1 2 calc R U P . .
C2 C 0.4643(3) 0.750000 0.5027(2) 0.0117(6) Uani 1 2 d S T P . .
C3 C 0.5372(3) 0.750000 0.4497(2) 0.0122(6) Uani 1 2 d S T P . .
C4 C 0.4958(3) 0.750000 0.3524(2) 0.0127(6) Uani 1 2 d S T P . .
H4 H 0.545018 0.750000 0.316553 0.015 Uiso 1 2 calc R U P . .
C4A C 0.3807(3) 0.750000 0.3083(2) 0.0121(6) Uani 1 2 d S T P . .
C4B C 0.3152(3) 0.750000 0.2089(2) 0.0119(6) Uani 1 2 d S T P . .
C5 C 0.3495(3) 0.750000 0.1303(2) 0.0144(6) Uani 1 2 d S T P . .
H5 H 0.426672 0.750000 0.136963 0.017 Uiso 1 2 calc R U P . .
C6 C 0.2691(3) 0.750000 0.0421(2) 0.0155(7) Uani 1 2 d S T P . .
H6 H 0.290387 0.750000 -0.012714 0.019 Uiso 1 2 calc R U P . .
C7 C 0.1567(3) 0.750000 0.0347(2) 0.0151(7) Uani 1 2 d S T P . .
C8 C 0.1208(3) 0.750000 0.1121(2) 0.0155(7) Uani 1 2 d S T P . .
H8 H 0.043528 0.750000 0.105108 0.019 Uiso 1 2 calc R U P . .
C8A C 0.2018(3) 0.750000 0.2002(2) 0.0128(6) Uani 1 2 d S T P . .
C9 C 0.1859(3) 0.750000 0.2963(2) 0.0133(6) Uani 1 2 d S T P . .
C9A C 0.3066(3) 0.750000 0.3603(2) 0.0116(6) Uani 1 2 d S T P . .
C10 C 0.1239(2) 0.5621(4) 0.31048(17) 0.0183(5) Uani 1 1 d . . . . .
H10A H 0.048243 0.561637 0.264816 0.027 Uiso 1 1 calc R U . . .
H10B H 0.119706 0.561853 0.374248 0.027 Uiso 1 1 calc R U . . .
H10C H 0.164048 0.442482 0.301420 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5109(3) 0.750000 0.6040(2) 0.0124(6) Uani 1 2 d S T P . .
C13 C 0.5115(3) 0.750000 0.7481(2) 0.0169(7) Uani 1 2 d S T P . .
C14 C 0.6217(3) 0.750000 0.7463(2) 0.0122(6) Uani 1 2 d S T P . .
C15 C 0.7100(3) 0.750000 0.8283(2) 0.0143(6) Uani 1 2 d S T P . .
H15 H 0.784586 0.750000 0.827501 0.017 Uiso 1 2 calc R U P . .
C15A C 0.6876(3) 0.750000 0.9136(2) 0.0149(7) Uani 1 2 d S T P . .
C16 C 0.7757(3) 0.750000 1.0008(2) 0.0184(7) Uani 1 2 d S T P . .
H16 H 0.850721 0.750000 1.001184 0.022 Uiso 1 2 calc R U P . .
C17 C 0.7551(3) 0.750000 1.0842(3) 0.0284(9) Uani 1 2 d S T P . .
H17 H 0.815323 0.750000 1.141903 0.034 Uiso 1 2 calc R U P . .
C18 C 0.6446(4) 0.750000 1.0842(3) 0.060(2) Uani 1 2 d S T P . .
H18 H 0.630168 0.750000 1.142168 0.072 Uiso 1 2 calc R U P . .
C19 C 0.5573(4) 0.750000 1.0017(3) 0.060(2) Uani 1 2 d S T P . .
H19 H 0.483011 0.750000 1.003334 0.071 Uiso 1 2 calc R U P . .
C19A C 0.5754(3) 0.750000 0.9138(3) 0.0263(9) Uani 1 2 d S T P . .
C20 C 0.4843(3) 0.750000 0.8280(3) 0.0307(10) Uani 1 2 d S T P . .
H20 H 0.408915 0.750000 0.826691 0.037 Uiso 1 2 calc R U P . .
Cl1 Cl 0.95883(15) 0.750000 0.48901(12) 0.0932(9) Uani 1 2 d S T P . .
Cl2 Cl 0.81292(11) 0.5372(3) 0.33062(10) 0.0812(4) Uani 1 1 d . . . . .
C21 C 0.8338(5) 0.750000 0.3995(4) 0.064(2) Uani 1 2 d S T P . .
H21 H 0.774333 0.749999 0.429626 0.076 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.900(3) . ?
O1 H1 0.8400 . ?
O1 C3 1.361(4) . ?
O2 C12 1.366(4) . ?
O2 C13 1.386(4) . ?
N1 C12 1.300(4) . ?
N1 C14 1.397(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.411(4) . ?
C1 C9A 1.384(4) . ?
C2 C3 1.406(4) . ?
C2 C12 1.446(4) . ?
C3 C4 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C4A 1.391(4) . ?
C4A C4B 1.455(4) . ?
C4A C9A 1.408(4) . ?
C4B C5 1.390(5) . ?
C4B C8A 1.401(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(5) . ?
C7 C8 1.385(5) . ?
C8 H8 0.9500 . ?
C8 C8A 1.387(5) . ?
C8A C9 1.526(5) . ?
C9 C9A 1.518(4) . ?
C9 C10 1.532(3) 4_575 ?
C9 C10 1.532(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 C14 1.406(5) . ?
C13 C20 1.357(5) . ?
C14 C15 1.367(5) . ?
C15 H15 0.9500 . ?
C15 C15A 1.406(5) . ?
C15A C16 1.418(5) . ?
C15A C19A 1.424(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.366(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.401(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.367(6) . ?
C19 H19 0.9500 . ?
C19 C19A 1.417(5) . ?
C19A C20 1.423(5) . ?
C20 H20 0.9500 . ?
Cl1 C21 1.712(6) . ?
Cl2 C21 1.727(4) . ?
C21 Cl2 1.727(4) 4_575 ?
C21 H21 1.0000 . ?

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
C3 O1 H1 109.5 . . ?
C12 O2 C13 104.0(3) . . ?
C12 N1 C14 105.3(3) . . ?
C2 C1 H1A 120.6 . . ?
C9A C1 H1A 120.6 . . ?
C9A C1 C2 118.8(3) . . ?
C1 C2 C12 120.7(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 C12 118.9(3) . . ?
O1 C3 C2 121.9(3) . . ?
O1 C3 C4 117.5(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C4A 118.6(3) . . ?
C4A C4 H4 120.7 . . ?
C4 C4A C4B 130.3(3) . . ?
C4 C4A C9A 121.4(3) . . ?
C9A C4A C4B 108.3(3) . . ?
C5 C4B C4A 130.1(3) . . ?
C5 C4B C8A 121.3(3) . . ?
C8A C4B C4A 108.5(3) . . ?
C4B C5 H5 120.7 . . ?
C6 C5 C4B 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.3(3) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 Br1 117.7(3) . . ?
C8 C7 Br1 119.4(3) . . ?
C8 C7 C6 122.9(3) . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C8A 117.5(3) . . ?
C8A C8 H8 121.2 . . ?
C4B C8A C9 111.3(3) . . ?
C8 C8A C4B 120.3(3) . . ?
C8 C8A C9 128.5(3) . . ?
C8A C9 C10 111.45(18) . 4_575 ?
C8A C9 C10 111.45(18) . . ?
C9A C9 C8A 100.6(3) . . ?
C9A C9 C10 111.59(18) . . ?
C9A C9 C10 111.60(18) . 4_575 ?
C10 C9 C10 109.9(3) . 4_575 ?
C1 C9A C4A 120.1(3) . . ?
C1 C9A C9 128.6(3) . . ?
C4A C9A C9 111.3(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C12 C2 119.2(3) . . ?
N1 C12 O2 115.3(3) . . ?
N1 C12 C2 125.5(3) . . ?
O2 C13 C14 107.7(3) . . ?
C20 C13 O2 128.3(3) . . ?
C20 C13 C14 124.1(3) . . ?
N1 C14 C13 107.7(3) . . ?
C15 C14 N1 131.9(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C15A 118.4(3) . . ?
C15A C15 H15 120.8 . . ?
C15 C15A C16 121.0(3) . . ?
C15 C15A C19A 120.2(3) . . ?
C16 C15A C19A 118.8(3) . . ?
C15A C16 H16 119.2 . . ?
C17 C16 C15A 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(4) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C19A 121.3(4) . . ?
C19A C19 H19 119.4 . . ?
C19 C19A C15A 118.1(3) . . ?
C19 C19A C20 121.2(4) . . ?
C20 C19A C15A 120.7(3) . . ?
C13 C20 C19A 116.1(3) . . ?
C13 C20 H20 121.9 . . ?
C19A C20 H20 121.9 . . ?
Cl1 C21 Cl2 113.2(2) . . ?
Cl1 C21 Cl2 113.2(2) . 4_575 ?
Cl1 C21 H21 106.5 . . ?
Cl2 C21 Cl2 110.6(3) . 4_575 ?
Cl2 C21 H21 106.5 4_575 . ?
Cl2 C21 H21 106.5 . . ?

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
Br1 C7 C8 C8A 180.000(0) . . . . ?
O1 C3 C4 C4A 180.000(1) . . . . ?
O2 C13 C14 N1 0.000(1) . . . . ?
O2 C13 C14 C15 180.000(1) . . . . ?
O2 C13 C20 C19A 180.000(2) . . . . ?
N1 C14 C15 C15A 180.000(2) . . . . ?
C1 C2 C3 O1 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C12 O2 0.000(1) . . . . ?
C1 C2 C12 N1 180.000(1) . . . . ?
C2 C1 C9A C4A 0.000(1) . . . . ?
C2 C1 C9A C9 180.000(1) . . . . ?
C2 C3 C4 C4A 0.000(1) . . . . ?
C3 C2 C12 O2 180.000(1) . . . . ?
C3 C2 C12 N1 0.000(1) . . . . ?
C3 C4 C4A C4B 180.000(1) . . . . ?
C3 C4 C4A C9A 0.000(1) . . . . ?
C4 C4A C4B C5 0.000(1) . . . . ?
C4 C4A C4B C8A 180.000(1) . . . . ?
C4 C4A C9A C1 0.000(1) . . . . ?
C4 C4A C9A C9 180.000(1) . . . . ?
C4A C4B C5 C6 180.000(0) . . . . ?
C4A C4B C8A C8 180.000(0) . . . . ?
C4A C4B C8A C9 0.000(0) . . . . ?
C4B C4A C9A C1 180.000(1) . . . . ?
C4B C4A C9A C9 0.000(1) . . . . ?
C4B C5 C6 C7 0.000(0) . . . . ?
C4B C8A C9 C9A 0.000(1) . . . . ?
C4B C8A C9 C10 118.41(19) . . . 4_575 ?
C4B C8A C9 C10 -118.40(19) . . . . ?
C5 C4B C8A C8 0.000(0) . . . . ?
C5 C4B C8A C9 180.000(0) . . . . ?
C5 C6 C7 Br1 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C6 C7 C8 C8A 0.000(0) . . . . ?
C7 C8 C8A C4B 0.000(0) . . . . ?
C7 C8 C8A C9 180.000(0) . . . . ?
C8 C8A C9 C9A 180.000(0) . . . . ?
C8 C8A C9 C10 -61.59(19) . . . 4_575 ?
C8 C8A C9 C10 61.60(19) . . . . ?
C8A C4B C5 C6 0.000(0) . . . . ?
C8A C9 C9A C1 180.000(1) . . . . ?
C8A C9 C9A C4A 0.000(1) . . . . ?
C9A C1 C2 C3 0.000(1) . . . . ?
C9A C1 C2 C12 180.000(1) . . . . ?
C9A C4A C4B C5 180.000(1) . . . . ?
C9A C4A C4B C8A 0.000(1) . . . . ?
C10 C9 C9A C1 -61.7(2) . . . . ?
C10 C9 C9A C1 61.7(2) 4_575 . . . ?
C10 C9 C9A C4A -118.3(2) 4_575 . . . ?
C10 C9 C9A C4A 118.3(2) . . . . ?
C12 O2 C13 C14 0.000(1) . . . . ?
C12 O2 C13 C20 180.000(2) . . . . ?
C12 N1 C14 C13 0.000(1) . . . . ?
C12 N1 C14 C15 180.000(2) . . . . ?
C12 C2 C3 O1 0.000(1) . . . . ?
C12 C2 C3 C4 180.000(1) . . . . ?
C13 O2 C12 N1 0.000(1) . . . . ?
C13 O2 C12 C2 180.000(1) . . . . ?
C13 C14 C15 C15A 0.000(2) . . . . ?
C14 N1 C12 O2 0.000(1) . . . . ?
C14 N1 C12 C2 180.000(1) . . . . ?
C14 C13 C20 C19A 0.000(2) . . . . ?
C14 C15 C15A C16 180.000(2) . . . . ?
C14 C15 C15A C19A 0.000(2) . . . . ?
C15 C15A C16 C17 180.000(2) . . . . ?
C15 C15A C19A C19 180.000(2) . . . . ?
C15 C15A C19A C20 0.000(2) . . . . ?
C15A C16 C17 C18 0.000(3) . . . . ?
C15A C19A C20 C13 0.000(2) . . . . ?
C16 C15A C19A C19 0.000(3) . . . . ?
C16 C15A C19A C20 180.000(2) . . . . ?
C16 C17 C18 C19 0.000(3) . . . . ?
C17 C18 C19 C19A 0.000(3) . . . . ?
C18 C19 C19A C15A 0.000(3) . . . . ?
C18 C19 C19A C20 180.000(2) . . . . ?
C19 C19A C20 C13 180.000(2) . . . . ?
C19A C15A C16 C17 0.000(2) . . . . ?
C20 C13 C14 N1 180.000(1) . . . . ?
C20 C13 C14 C15 0.000(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld200211_0ma
_database_code_depnum_ccdc_archive 'CCDC 2018050'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-04-02
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N2 O3'
_chemical_formula_sum            'C25 H28 N2 O3'
_chemical_formula_weight         404.49
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.1266(4)
_cell_length_b                   21.0008(9)
_cell_length_c                   10.2483(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2179.47(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4562
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.9516.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.939
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4854
_reflns_number_total             5406
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1981 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.030
_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)+(0.0520P)²+0.5121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0968
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.27553(15) 0.38886(7) 0.04060(16) 0.0193(3) Uani 1 1 d . . . . .
H1 H 0.331463 0.365033 0.004820 0.029 Uiso 1 1 calc R U . . .
O2 O 0.61745(15) 0.30578(7) 0.19681(15) 0.0174(3) Uani 1 1 d . . . . .
O3 O 0.02154(17) 0.65488(8) 0.77346(18) 0.0250(4) Uani 1 1 d . . . . .
N1 N 0.48706(18) 0.31839(8) 0.01992(18) 0.0158(4) Uani 1 1 d . . . . .
N2 N 0.1639(2) 0.60247(9) 0.9061(2) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.4528(2) 0.37881(10) 0.3550(2) 0.0147(4) Uani 1 1 d . . . . .
H1A H 0.527835 0.358789 0.392585 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4203(2) 0.36783(10) 0.2237(2) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.3085(2) 0.39758(10) 0.1678(2) 0.0137(4) Uani 1 1 d . . . . .
C4 C 0.2316(2) 0.43882(10) 0.2421(2) 0.0143(4) Uani 1 1 d . . . . .
H4 H 0.157419 0.459675 0.204814 0.017 Uiso 1 1 calc R U . . .
C4A C 0.2653(2) 0.44886(9) 0.3715(2) 0.0131(4) Uani 1 1 d . . . . .
C4B C 0.2065(2) 0.49165(9) 0.4686(2) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.0982(2) 0.53231(10) 0.4605(2) 0.0161(4) Uani 1 1 d . . . . .
H5 H 0.045776 0.533866 0.383669 0.019 Uiso 1 1 calc R U . . .
C6 C 0.0683(2) 0.57060(10) 0.5673(2) 0.0169(4) Uani 1 1 d . . . . .
H6 H -0.004510 0.599033 0.563162 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1447(2) 0.56754(10) 0.6805(2) 0.0169(4) Uani 1 1 d . . . . .
C8 C 0.2515(2) 0.52537(10) 0.6897(2) 0.0169(4) Uani 1 1 d . . . . .
H8 H 0.302427 0.522852 0.767367 0.020 Uiso 1 1 calc R U . . .
C8A C 0.2814(2) 0.48759(10) 0.5836(2) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.3923(2) 0.43895(10) 0.5704(2) 0.0144(4) Uani 1 1 d . . . . .
C9A C 0.3751(2) 0.41887(10) 0.4288(2) 0.0134(4) Uani 1 1 d . . . . .
C10 C 0.3706(2) 0.38269(11) 0.6631(2) 0.0215(5) Uani 1 1 d . . . . .
H10A H 0.282585 0.364674 0.648583 0.032 Uiso 1 1 calc R U . . .
H10B H 0.377833 0.397378 0.753632 0.032 Uiso 1 1 calc R U . . .
H10C H 0.437651 0.350012 0.646536 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5285(2) 0.46918(11) 0.5940(3) 0.0214(5) Uani 1 1 d . . . . .
H11A H 0.535331 0.482819 0.685196 0.032 Uiso 1 1 calc R U . . .
H11B H 0.539384 0.506134 0.536583 0.032 Uiso 1 1 calc R U . . .
H11C H 0.597695 0.437861 0.575197 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5066(2) 0.32928(10) 0.1410(2) 0.0141(4) Uani 1 1 d . . . . .
C13 C 0.6772(2) 0.26586(11) 0.0966(2) 0.0210(5) Uani 1 1 d . . . . .
H13A H 0.662575 0.220181 0.115515 0.025 Uiso 1 1 calc R U . . .
H13B H 0.773391 0.273842 0.090326 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6065(2) 0.28561(10) -0.0305(2) 0.0165(4) Uani 1 1 d . . . . .
C15 C 0.5674(3) 0.22885(11) -0.1140(3) 0.0258(5) Uani 1 1 d . . . . .
H15A H 0.510298 0.200410 -0.063383 0.039 Uiso 1 1 calc R U . . .
H15B H 0.646875 0.205769 -0.141173 0.039 Uiso 1 1 calc R U . . .
H15C H 0.519712 0.243790 -0.191429 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6860(2) 0.33381(13) -0.1081(3) 0.0265(5) Uani 1 1 d . . . . .
H16A H 0.632423 0.349806 -0.180680 0.040 Uiso 1 1 calc R U . . .
H16B H 0.765746 0.313403 -0.142409 0.040 Uiso 1 1 calc R U . . .
H16C H 0.710967 0.369343 -0.051225 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1138(2) 0.60801(10) 0.7942(2) 0.0178(5) Uani 1 1 d . . . . .
C18 C -0.0071(2) 0.67992(12) 0.9026(3) 0.0268(6) Uani 1 1 d . . . . .
H18A H -0.094267 0.665017 0.933765 0.032 Uiso 1 1 calc R U . . .
H18B H -0.006247 0.727064 0.902254 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1046(2) 0.65349(11) 0.9885(2) 0.0220(5) Uani 1 1 d . . . . .
C20 C 0.0538(3) 0.62311(13) 1.1144(3) 0.0326(6) Uani 1 1 d . . . . .
H20A H -0.005887 0.587896 1.092937 0.049 Uiso 1 1 calc R U . . .
H20B H 0.006092 0.655067 1.165724 0.049 Uiso 1 1 calc R U . . .
H20C H 0.128557 0.606903 1.165181 0.049 Uiso 1 1 calc R U . . .
C21 C 0.2101(3) 0.70358(12) 1.0172(3) 0.0286(6) Uani 1 1 d . . . . .
H21A H 0.283426 0.683796 1.064624 0.043 Uiso 1 1 calc R U . . .
H21B H 0.171828 0.737677 1.070375 0.043 Uiso 1 1 calc R U . . .
H21C H 0.242762 0.721396 0.934881 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C3 1.359(3) . ?
O2 C12 1.353(3) . ?
O2 C13 1.458(3) . ?
O3 C17 1.373(3) . ?
O3 C18 1.453(3) . ?
N1 C12 1.277(3) . ?
N1 C14 1.485(3) . ?
N2 C17 1.259(3) . ?
N2 C19 1.490(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.404(3) . ?
C1 C9A 1.379(3) . ?
C2 C3 1.414(3) . ?
C2 C12 1.462(3) . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C4A 1.385(3) . ?
C4A C4B 1.467(3) . ?
C4A C9A 1.406(3) . ?
C4B C5 1.393(3) . ?
C4B C8A 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C7 C8 1.401(3) . ?
C7 C17 1.476(3) . ?
C8 H8 0.9500 . ?
C8 C8A 1.379(3) . ?
C8A C9 1.524(3) . ?
C9 C9A 1.521(3) . ?
C9 C10 1.532(3) . ?
C9 C11 1.538(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.543(3) . ?
C14 C15 1.520(3) . ?
C14 C16 1.518(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.537(4) . ?
C19 C20 1.528(4) . ?
C19 C21 1.528(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C12 O2 C13 104.85(17) . . ?
C17 O3 C18 104.70(18) . . ?
C12 N1 C14 107.15(18) . . ?
C17 N2 C19 106.69(19) . . ?
C2 C1 H1A 120.2 . . ?
C9A C1 H1A 120.2 . . ?
C9A C1 C2 119.52(19) . . ?
C1 C2 C3 120.19(19) . . ?
C1 C2 C12 120.44(19) . . ?
C3 C2 C12 119.23(19) . . ?
O1 C3 C2 121.73(19) . . ?
O1 C3 C4 118.11(19) . . ?
C4 C3 C2 120.1(2) . . ?
C3 C4 H4 120.7 . . ?
C4A C4 C3 118.70(19) . . ?
C4A C4 H4 120.7 . . ?
C4 C4A C4B 130.0(2) . . ?
C4 C4A C9A 121.78(19) . . ?
C9A C4A C4B 108.16(19) . . ?
C5 C4B C4A 130.9(2) . . ?
C5 C4B C8A 120.8(2) . . ?
C8A C4B C4A 108.24(18) . . ?
C4B C5 H5 120.7 . . ?
C6 C5 C4B 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 C17 120.8(2) . . ?
C8 C7 C17 118.4(2) . . ?
C7 C8 H8 120.7 . . ?
C8A C8 C7 118.7(2) . . ?
C8A C8 H8 120.7 . . ?
C4B C8A C9 111.38(19) . . ?
C8 C8A C4B 120.56(19) . . ?
C8 C8A C9 128.1(2) . . ?
C8A C9 C10 110.90(18) . . ?
C8A C9 C11 111.75(17) . . ?
C9A C9 C8A 100.72(17) . . ?
C9A C9 C10 111.19(17) . . ?
C9A C9 C11 111.50(18) . . ?
C10 C9 C11 110.45(19) . . ?
C1 C9A C4A 119.7(2) . . ?
C1 C9A C9 128.90(19) . . ?
C4A C9A C9 111.40(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C2 116.89(19) . . ?
N1 C12 O2 118.3(2) . . ?
N1 C12 C2 124.8(2) . . ?
O2 C13 H13A 110.9 . . ?
O2 C13 H13B 110.9 . . ?
O2 C13 C14 104.32(16) . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
N1 C14 C13 102.08(18) . . ?
N1 C14 C15 110.30(18) . . ?
N1 C14 C16 107.75(18) . . ?
C15 C14 C13 112.68(19) . . ?
C16 C14 C13 112.06(19) . . ?
C16 C14 C15 111.5(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C7 115.8(2) . . ?
N2 C17 O3 118.8(2) . . ?
N2 C17 C7 125.5(2) . . ?
O3 C18 H18A 110.9 . . ?
O3 C18 H18B 110.9 . . ?
O3 C18 C19 104.15(18) . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
N2 C19 C18 103.4(2) . . ?
N2 C19 C20 108.27(19) . . ?
N2 C19 C21 108.80(19) . . ?
C20 C19 C18 112.8(2) . . ?
C21 C19 C18 112.1(2) . . ?
C21 C19 C20 111.1(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C3 C4 C4A -179.06(18) . . . . ?
O2 C13 C14 N1 -17.8(2) . . . . ?
O2 C13 C14 C15 -136.1(2) . . . . ?
O2 C13 C14 C16 97.2(2) . . . . ?
O3 C18 C19 N2 -14.6(2) . . . . ?
O3 C18 C19 C20 -131.3(2) . . . . ?
O3 C18 C19 C21 102.4(2) . . . . ?
C1 C2 C3 O1 178.87(19) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C1 C2 C12 O2 -0.5(3) . . . . ?
C1 C2 C12 N1 -177.8(2) . . . . ?
C2 C1 C9A C4A -0.8(3) . . . . ?
C2 C1 C9A C9 -178.5(2) . . . . ?
C2 C3 C4 C4A -1.3(3) . . . . ?
C3 C2 C12 O2 175.20(18) . . . . ?
C3 C2 C12 N1 -2.1(3) . . . . ?
C3 C4 C4A C4B 176.5(2) . . . . ?
C3 C4 C4A C9A 0.4(3) . . . . ?
C4 C4A C4B C5 2.7(4) . . . . ?
C4 C4A C4B C8A -176.2(2) . . . . ?
C4 C4A C9A C1 0.7(3) . . . . ?
C4 C4A C9A C9 178.75(18) . . . . ?
C4A C4B C5 C6 -176.5(2) . . . . ?
C4A C4B C8A C8 176.91(18) . . . . ?
C4A C4B C8A C9 -2.4(2) . . . . ?
C4B C4A C9A C1 -176.19(19) . . . . ?
C4B C4A C9A C9 1.9(2) . . . . ?
C4B C5 C6 C7 -0.8(3) . . . . ?
C4B C8A C9 C9A 3.3(2) . . . . ?
C4B C8A C9 C10 -114.5(2) . . . . ?
C4B C8A C9 C11 121.8(2) . . . . ?
C5 C4B C8A C8 -2.1(3) . . . . ?
C5 C4B C8A C9 178.57(19) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C5 C6 C7 C17 179.97(19) . . . . ?
C6 C7 C8 C8A 1.1(3) . . . . ?
C6 C7 C17 O3 -10.3(3) . . . . ?
C6 C7 C17 N2 169.2(2) . . . . ?
C7 C8 C8A C4B 0.4(3) . . . . ?
C7 C8 C8A C9 179.6(2) . . . . ?
C8 C7 C17 O3 170.58(19) . . . . ?
C8 C7 C17 N2 -9.9(3) . . . . ?
C8 C8A C9 C9A -176.0(2) . . . . ?
C8 C8A C9 C10 66.2(3) . . . . ?
C8 C8A C9 C11 -57.5(3) . . . . ?
C8A C4B C5 C6 2.3(3) . . . . ?
C8A C9 C9A C1 174.7(2) . . . . ?
C8A C9 C9A C4A -3.1(2) . . . . ?
C9A C1 C2 C3 -0.1(3) . . . . ?
C9A C1 C2 C12 175.5(2) . . . . ?
C9A C4A C4B C5 179.2(2) . . . . ?
C9A C4A C4B C8A 0.4(2) . . . . ?
C10 C9 C9A C1 -67.7(3) . . . . ?
C10 C9 C9A C4A 114.5(2) . . . . ?
C11 C9 C9A C1 56.1(3) . . . . ?
C11 C9 C9A C4A -121.77(19) . . . . ?
C12 O2 C13 C14 15.3(2) . . . . ?
C12 N1 C14 C13 14.3(2) . . . . ?
C12 N1 C14 C15 134.3(2) . . . . ?
C12 N1 C14 C16 -103.8(2) . . . . ?
C12 C2 C3 O1 3.2(3) . . . . ?
C12 C2 C3 C4 -174.50(18) . . . . ?
C13 O2 C12 N1 -6.9(2) . . . . ?
C13 O2 C12 C2 175.57(18) . . . . ?
C14 N1 C12 O2 -5.3(3) . . . . ?
C14 N1 C12 C2 171.94(19) . . . . ?
C17 O3 C18 C19 14.0(2) . . . . ?
C17 N2 C19 C18 9.9(2) . . . . ?
C17 N2 C19 C20 129.7(2) . . . . ?
C17 N2 C19 C21 -109.4(2) . . . . ?
C17 C7 C8 C8A -179.74(19) . . . . ?
C18 O3 C17 N2 -8.9(3) . . . . ?
C18 O3 C17 C7 170.60(19) . . . . ?
C19 N2 C17 O3 -1.0(3) . . . . ?
C19 N2 C17 C7 179.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld180430_0ma
_database_code_depnum_ccdc_archive 'CCDC 2018046'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-04-03
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N O S'
_chemical_formula_sum            'C22 H16 Br N O S'
_chemical_formula_weight         422.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.5848(3)
_cell_length_b                   6.8902(3)
_cell_length_c                   15.8079(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.9800(10)
_cell_angle_gamma                90
_cell_volume                     923.59(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9426
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.720
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1376 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.7846.
The λ/2 correction factor is Not present.
;
_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    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29406
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.341
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2315
_reflns_number_total             2485
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0080(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.076
_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)+(0.0294P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C16(H15), C17(H16), C18(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Br1 Br 0.71311(3) 0.750000 -0.01885(2) 0.03325(10) Uani 1 2 d S T P . .
S1 S 0.14880(5) 0.750000 0.55216(3) 0.01668(11) Uani 1 2 d S T P . .
O1 O 0.69283(15) 0.750000 0.58265(9) 0.0190(3) Uani 1 2 d S T P . .
H1 H 0.634(3) 0.750000 0.6182(17) 0.025(7) Uiso 1 2 d S . P . .
N1 N 0.42667(17) 0.750000 0.64441(10) 0.0146(3) Uani 1 2 d S T P . .
C1 C 0.3546(2) 0.750000 0.40707(11) 0.0147(3) Uani 1 2 d S T P . .
H1A H 0.242574 0.750000 0.398003 0.018 Uiso 1 2 calc R U P . .
C2 C 0.4387(2) 0.750000 0.49138(11) 0.0138(3) Uani 1 2 d S T P . .
C3 C 0.6056(2) 0.750000 0.50323(12) 0.0149(3) Uani 1 2 d S T P . .
C4B C 0.6524(2) 0.750000 0.26770(12) 0.0147(3) Uani 1 2 d S T P . .
C4 C 0.6861(2) 0.750000 0.43357(12) 0.0153(3) Uani 1 2 d S T P . .
H4 H 0.798105 0.750000 0.441947 0.018 Uiso 1 2 calc R U P . .
C4A C 0.6002(2) 0.750000 0.35130(12) 0.0142(3) Uani 1 2 d S T P . .
C5 C 0.8033(2) 0.750000 0.24610(12) 0.0167(3) Uani 1 2 d S T P . .
H5 H 0.893391 0.750000 0.289474 0.020 Uiso 1 2 calc R U P . .
C6 C 0.8204(2) 0.750000 0.16010(12) 0.0182(4) Uani 1 2 d S T P . .
H6 H 0.922461 0.750000 0.143903 0.022 Uiso 1 2 calc R U P . .
C7 C 0.6861(2) 0.750000 0.09790(12) 0.0189(4) Uani 1 2 d S T P . .
C8A C 0.5184(2) 0.750000 0.20380(12) 0.0149(3) Uani 1 2 d S T P . .
C8 C 0.5344(2) 0.750000 0.11828(12) 0.0178(4) Uani 1 2 d S T P . .
H8 H 0.444613 0.750000 0.074740 0.021 Uiso 1 2 calc R U P . .
C9A C 0.4340(2) 0.750000 0.33840(11) 0.0140(3) Uani 1 2 d S T P . .
C9 C 0.3675(2) 0.750000 0.24323(11) 0.0142(3) Uani 1 2 d S T P . .
C10 C 0.26768(14) 0.56783(19) 0.21814(8) 0.0175(3) Uani 1 1 d . . . . .
H10A H 0.175356 0.568472 0.247611 0.026 Uiso 1 1 calc R U . . .
H10B H 0.331121 0.451765 0.234743 0.026 Uiso 1 1 calc R U . . .
H10C H 0.232900 0.567046 0.156075 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3554(2) 0.750000 0.56446(12) 0.0149(3) Uani 1 2 d S T P . .
C12 C 0.1598(2) 0.750000 0.66275(12) 0.0160(3) Uani 1 2 d S T P . .
C13 C 0.3194(2) 0.750000 0.70140(12) 0.0149(3) Uani 1 2 d S T P . .
C14 C 0.3566(2) 0.750000 0.79077(12) 0.0164(3) Uani 1 2 d S T P . .
H14 H 0.463(3) 0.750000 0.8181(14) 0.015(5) Uiso 1 2 d S . P . .
C15 C 0.2355(2) 0.750000 0.83904(12) 0.0180(4) Uani 1 2 d S T P . .
H15 H 0.259694 0.750000 0.899773 0.022 Uiso 1 2 calc R U P . .
C16 C 0.0775(2) 0.750000 0.79956(13) 0.0195(4) Uani 1 2 d S T P . .
H16 H -0.003743 0.750000 0.834047 0.023 Uiso 1 2 calc R U P . .
C17 C 0.0377(2) 0.750000 0.71138(13) 0.0182(4) Uani 1 2 d S T P . .
H17 H -0.069483 0.750000 0.684788 0.022 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.8959(19) . ?
S1 C11 1.7539(18) . ?
S1 C12 1.7359(19) . ?
O1 H1 0.81(3) . ?
O1 C3 1.358(2) . ?
N1 C11 1.315(2) . ?
N1 C13 1.385(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.413(2) . ?
C1 C9A 1.369(3) . ?
C2 C3 1.416(2) . ?
C2 C11 1.450(3) . ?
C3 C4 1.388(3) . ?
C4B C4A 1.460(3) . ?
C4B C5 1.391(2) . ?
C4B C8A 1.407(2) . ?
C4 H4 0.9500 . ?
C4 C4A 1.391(2) . ?
C4A C9A 1.409(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(3) . ?
C7 C8 1.389(3) . ?
C8A C8 1.380(3) . ?
C8A C9 1.523(2) . ?
C8 H8 0.9500 . ?
C9A C9 1.524(2) . ?
C9 C10 1.5364(15) 4_575 ?
C9 C10 1.5365(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.410(2) . ?
C12 C17 1.393(3) . ?
C13 C14 1.399(3) . ?
C14 H14 0.95(2) . ?
C14 C15 1.382(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.402(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C11 89.61(9) . . ?
C3 O1 H1 109.1(18) . . ?
C11 N1 C13 111.60(15) . . ?
C2 C1 H1A 119.9 . . ?
C9A C1 H1A 119.9 . . ?
C9A C1 C2 120.23(16) . . ?
C1 C2 C3 118.82(16) . . ?
C1 C2 C11 120.57(16) . . ?
C3 C2 C11 120.61(15) . . ?
O1 C3 C2 121.52(17) . . ?
O1 C3 C4 117.56(16) . . ?
C4 C3 C2 120.91(16) . . ?
C5 C4B C4A 130.64(17) . . ?
C5 C4B C8A 120.81(17) . . ?
C8A C4B C4A 108.55(16) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C4A 119.00(16) . . ?
C4A C4 H4 120.5 . . ?
C4 C4A C4B 130.81(16) . . ?
C4 C4A C9A 120.80(17) . . ?
C9A C4A C4B 108.39(15) . . ?
C4B C5 H5 120.5 . . ?
C6 C5 C4B 119.01(17) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.18(17) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 Br1 118.22(14) . . ?
C8 C7 Br1 119.17(14) . . ?
C8 C7 C6 122.61(18) . . ?
C4B C8A C9 111.00(16) . . ?
C8 C8A C4B 120.53(17) . . ?
C8 C8A C9 128.47(16) . . ?
C7 C8 H8 121.1 . . ?
C8A C8 C7 117.87(17) . . ?
C8A C8 H8 121.1 . . ?
C1 C9A C4A 120.23(16) . . ?
C1 C9A C9 128.78(15) . . ?
C4A C9A C9 110.99(15) . . ?
C8A C9 C9A 101.07(13) . . ?
C8A C9 C10 111.72(10) . 4_575 ?
C8A C9 C10 111.72(10) . . ?
C9A C9 C10 111.28(9) . 4_575 ?
C9A C9 C10 111.28(9) . . ?
C10 C9 C10 109.56(14) 4_575 . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 S1 114.65(14) . . ?
N1 C11 C2 123.52(16) . . ?
C2 C11 S1 121.83(13) . . ?
C13 C12 S1 109.45(14) . . ?
C17 C12 S1 128.92(14) . . ?
C17 C12 C13 121.64(17) . . ?
N1 C13 C12 114.69(16) . . ?
N1 C13 C14 125.89(16) . . ?
C14 C13 C12 119.42(17) . . ?
C13 C14 H14 120.8(13) . . ?
C15 C14 C13 118.97(16) . . ?
C15 C14 H14 120.2(13) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.87(17) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.24(18) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 121.1 . . ?
C16 C17 C12 117.86(17) . . ?
C16 C17 H17 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 C8A 180.000(0) . . . . ?
S1 C12 C13 N1 0.000(1) . . . . ?
S1 C12 C13 C14 180.000(1) . . . . ?
S1 C12 C17 C16 180.000(1) . . . . ?
O1 C3 C4 C4A 180.000(0) . . . . ?
N1 C13 C14 C15 180.000(1) . . . . ?
C1 C2 C3 O1 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C11 S1 0.000(1) . . . . ?
C1 C2 C11 N1 180.000(1) . . . . ?
C1 C9A C9 C8A 180.000(0) . . . . ?
C1 C9A C9 C10 -61.25(10) . . . . ?
C1 C9A C9 C10 61.25(10) . . . 4_575 ?
C2 C1 C9A C4A 0.000(0) . . . . ?
C2 C1 C9A C9 180.000(0) . . . . ?
C2 C3 C4 C4A 0.000(1) . . . . ?
C3 C2 C11 S1 180.000(0) . . . . ?
C3 C2 C11 N1 0.000(1) . . . . ?
C3 C4 C4A C4B 180.000(0) . . . . ?
C3 C4 C4A C9A 0.000(1) . . . . ?
C4B C4A C9A C1 180.000(0) . . . . ?
C4B C4A C9A C9 0.000(0) . . . . ?
C4B C5 C6 C7 0.000(0) . . . . ?
C4B C8A C8 C7 0.000(0) . . . . ?
C4B C8A C9 C9A 0.000(0) . . . . ?
C4B C8A C9 C10 -118.43(10) . . . . ?
C4B C8A C9 C10 118.43(10) . . . 4_575 ?
C4 C4A C9A C1 0.000(0) . . . . ?
C4 C4A C9A C9 180.000(0) . . . . ?
C4A C4B C5 C6 180.000(0) . . . . ?
C4A C4B C8A C8 180.000(0) . . . . ?
C4A C4B C8A C9 0.000(0) . . . . ?
C4A C9A C9 C8A 0.000(0) . . . . ?
C4A C9A C9 C10 -118.75(10) . . . 4_575 ?
C4A C9A C9 C10 118.75(10) . . . . ?
C5 C4B C4A C4 0.000(1) . . . . ?
C5 C4B C4A C9A 180.000(0) . . . . ?
C5 C4B C8A C8 0.000(0) . . . . ?
C5 C4B C8A C9 180.000(0) . . . . ?
C5 C6 C7 Br1 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C6 C7 C8 C8A 0.000(0) . . . . ?
C8A C4B C4A C4 180.000(0) . . . . ?
C8A C4B C4A C9A 0.000(0) . . . . ?
C8A C4B C5 C6 0.000(0) . . . . ?
C8 C8A C9 C9A 180.000(0) . . . . ?
C8 C8A C9 C10 61.57(10) . . . . ?
C8 C8A C9 C10 -61.57(10) . . . 4_575 ?
C9A C1 C2 C3 0.000(1) . . . . ?
C9A C1 C2 C11 180.000(0) . . . . ?
C9 C8A C8 C7 180.000(0) . . . . ?
C11 S1 C12 C13 0.000(0) . . . . ?
C11 S1 C12 C17 180.000(1) . . . . ?
C11 N1 C13 C12 0.000(1) . . . . ?
C11 N1 C13 C14 180.000(1) . . . . ?
C11 C2 C3 O1 0.000(1) . . . . ?
C11 C2 C3 C4 180.000(1) . . . . ?
C12 S1 C11 N1 0.000(0) . . . . ?
C12 S1 C11 C2 180.000(0) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
C13 N1 C11 S1 0.000(1) . . . . ?
C13 N1 C11 C2 180.000(1) . . . . ?
C13 C12 C17 C16 0.000(1) . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C14 C15 C16 C17 0.000(1) . . . . ?
C15 C16 C17 C12 0.000(1) . . . . ?
C17 C12 C13 N1 180.000(1) . . . . ?
C17 C12 C13 C14 0.000(1) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld200205_0ma
_database_code_depnum_ccdc_archive 'CCDC 2018049'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-04-02
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N O Se'
_chemical_formula_sum            'C22 H16 Br N O Se'
_chemical_formula_weight         469.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   30.762(3)
_cell_length_b                   10.8014(11)
_cell_length_c                   11.0953(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3686.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.98
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.501
_shelx_estimated_absorpt_T_min   0.385
_exptl_absorpt_coefficient_mu    4.215
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.7278.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            203320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.294
_diffrn_reflns_theta_min         1.998
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6035
_reflns_number_total             7095
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         7095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²+3.6064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0593
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.75975(2) 0.43485(2) 0.15593(2) 0.02722(4) Uani 1 1 d . . . . .
Se1 Se 0.45149(2) 0.18524(2) 0.59074(2) 0.01386(3) Uani 1 1 d . . . . .
O1 O 0.45621(3) 0.51445(10) 0.30529(10) 0.0172(2) Uani 1 1 d . . . . .
H1 H 0.435370 0.485411 0.345205 0.026 Uiso 1 1 calc R U . . .
N1 N 0.41550(4) 0.36527(11) 0.45140(11) 0.0132(2) Uani 1 1 d . . . . .
C1 C 0.53298(4) 0.29463(12) 0.44432(12) 0.0123(2) Uani 1 1 d . . . . .
H1A H 0.533607 0.228458 0.500700 0.015 Uiso 1 1 calc R U . . .
C2 C 0.49334(4) 0.35345(12) 0.41733(12) 0.0118(2) Uani 1 1 d . . . . .
C3 C 0.49304(4) 0.45351(12) 0.33422(12) 0.0125(2) Uani 1 1 d . . . . .
C4 C 0.53132(4) 0.49114(12) 0.27785(12) 0.0135(2) Uani 1 1 d . . . . .
H4 H 0.531096 0.557100 0.221215 0.016 Uiso 1 1 calc R U . . .
C4A C 0.56975(4) 0.43044(12) 0.30601(11) 0.0113(2) Uani 1 1 d . . . . .
C4B C 0.61394(4) 0.45008(12) 0.26115(11) 0.0111(2) Uani 1 1 d . . . . .
C5 C 0.62973(5) 0.53237(13) 0.17532(12) 0.0144(2) Uani 1 1 d . . . . .
H5 H 0.610875 0.590682 0.138218 0.017 Uiso 1 1 calc R U . . .
C6 C 0.67345(5) 0.52804(13) 0.14462(13) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.684865 0.582664 0.085435 0.020 Uiso 1 1 calc R U . . .
C7 C 0.70037(5) 0.44254(13) 0.20177(13) 0.0159(2) Uani 1 1 d . . . . .
C8 C 0.68545(4) 0.36096(12) 0.28938(12) 0.0135(2) Uani 1 1 d . . . . .
H8 H 0.704562 0.304400 0.328003 0.016 Uiso 1 1 calc R U . . .
C8A C 0.64169(4) 0.36523(12) 0.31825(11) 0.0108(2) Uani 1 1 d . . . . .
C9 C 0.61679(4) 0.28383(11) 0.40639(11) 0.0104(2) Uani 1 1 d . . . . .
C9A C 0.57088(4) 0.33252(12) 0.38941(11) 0.0109(2) Uani 1 1 d . . . . .
C10 C 0.63233(4) 0.30327(13) 0.53658(12) 0.0142(2) Uani 1 1 d . . . . .
H10A H 0.662794 0.277743 0.543537 0.021 Uiso 1 1 calc R U . . .
H10B H 0.614453 0.253501 0.591330 0.021 Uiso 1 1 calc R U . . .
H10C H 0.629649 0.390981 0.557922 0.021 Uiso 1 1 calc R U . . .
C11 C 0.62076(4) 0.14613(12) 0.37353(13) 0.0141(2) Uani 1 1 d . . . . .
H11A H 0.610667 0.133386 0.290680 0.021 Uiso 1 1 calc R U . . .
H11B H 0.602943 0.096798 0.428797 0.021 Uiso 1 1 calc R U . . .
H11C H 0.651214 0.120356 0.380150 0.021 Uiso 1 1 calc R U . . .
C12 C 0.45307(4) 0.31421(12) 0.47411(12) 0.0123(2) Uani 1 1 d . . . . .
C13 C 0.39175(4) 0.22078(12) 0.59942(12) 0.0128(2) Uani 1 1 d . . . . .
C14 C 0.38151(4) 0.31618(12) 0.51819(12) 0.0125(2) Uani 1 1 d . . . . .
C15 C 0.33853(4) 0.35741(13) 0.50922(13) 0.0153(2) Uani 1 1 d . . . . .
H15 H 0.331043 0.420724 0.453532 0.018 Uiso 1 1 calc R U . . .
C16 C 0.30705(4) 0.30519(13) 0.58210(14) 0.0171(3) Uani 1 1 d . . . . .
H16 H 0.277888 0.333697 0.577060 0.020 Uiso 1 1 calc R U . . .
C17 C 0.31767(5) 0.21081(13) 0.66319(14) 0.0171(3) Uani 1 1 d . . . . .
H17 H 0.295633 0.175994 0.712676 0.021 Uiso 1 1 calc R U . . .
C18 C 0.36007(5) 0.16730(13) 0.67231(13) 0.0156(2) Uani 1 1 d . . . . .
H18 H 0.367241 0.102698 0.726907 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.8981(14) . ?
Se1 C12 1.9019(13) . ?
Se1 C13 1.8796(13) . ?
O1 H1 0.8400 . ?
O1 C3 1.3489(16) . ?
N1 C12 1.3050(16) . ?
N1 C14 1.3872(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.4071(18) . ?
C1 C9A 1.3777(18) . ?
C2 C3 1.4208(18) . ?
C2 C12 1.4531(18) . ?
C3 C4 1.3939(19) . ?
C4 H4 0.9500 . ?
C4 C4A 1.3874(18) . ?
C4A C4B 1.4631(18) . ?
C4A C9A 1.4057(17) . ?
C4B C5 1.3903(18) . ?
C4B C8A 1.4037(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(2) . ?
C7 C8 1.3900(19) . ?
C8 H8 0.9500 . ?
C8 C8A 1.3845(18) . ?
C8A C9 1.5219(18) . ?
C9 C9A 1.5187(18) . ?
C9 C10 1.5359(18) . ?
C9 C11 1.5363(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.4048(19) . ?
C13 C18 1.3920(19) . ?
C14 C15 1.3986(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 Se1 C12 84.85(6) . . ?
C3 O1 H1 109.5 . . ?
C12 N1 C14 113.75(12) . . ?
C2 C1 H1A 119.8 . . ?
C9A C1 H1A 119.8 . . ?
C9A C1 C2 120.33(12) . . ?
C1 C2 C3 119.16(12) . . ?
C1 C2 C12 120.99(12) . . ?
C3 C2 C12 119.85(11) . . ?
O1 C3 C2 122.08(12) . . ?
O1 C3 C4 117.41(12) . . ?
C4 C3 C2 120.50(12) . . ?
C3 C4 H4 120.6 . . ?
C4A C4 C3 118.75(12) . . ?
C4A C4 H4 120.6 . . ?
C4 C4A C4B 130.28(12) . . ?
C4 C4A C9A 121.66(12) . . ?
C9A C4A C4B 108.06(11) . . ?
C5 C4B C4A 130.57(12) . . ?
C5 C4B C8A 120.94(12) . . ?
C8A C4B C4A 108.47(11) . . ?
C4B C5 H5 120.5 . . ?
C6 C5 C4B 119.02(13) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.11(13) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 Br1 118.62(10) . . ?
C8 C7 Br1 118.52(11) . . ?
C8 C7 C6 122.84(13) . . ?
C7 C8 H8 121.2 . . ?
C8A C8 C7 117.50(13) . . ?
C8A C8 H8 121.2 . . ?
C4B C8A C9 111.17(11) . . ?
C8 C8A C4B 120.57(12) . . ?
C8 C8A C9 128.23(12) . . ?
C8A C9 C10 111.63(10) . . ?
C8A C9 C11 111.51(11) . . ?
C9A C9 C8A 100.85(10) . . ?
C9A C9 C10 111.02(11) . . ?
C9A C9 C11 112.33(10) . . ?
C10 C9 C11 109.32(11) . . ?
C1 C9A C4A 119.58(12) . . ?
C1 C9A C9 128.99(11) . . ?
C4A C9A C9 111.43(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 Se1 114.73(10) . . ?
N1 C12 C2 123.22(12) . . ?
C2 C12 Se1 122.03(9) . . ?
C14 C13 Se1 109.65(9) . . ?
C18 C13 Se1 129.02(11) . . ?
C18 C13 C14 121.33(12) . . ?
N1 C14 C13 117.00(11) . . ?
N1 C14 C15 123.57(12) . . ?
C15 C14 C13 119.43(12) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.39(13) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.68(13) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.84(13) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.8 . . ?
C17 C18 C13 118.32(13) . . ?
C17 C18 H18 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 C8A -177.72(10) . . . . ?
Se1 C13 C14 N1 -0.86(15) . . . . ?
Se1 C13 C14 C15 179.73(10) . . . . ?
Se1 C13 C18 C17 179.27(11) . . . . ?
O1 C3 C4 C4A 179.82(12) . . . . ?
N1 C14 C15 C16 -178.12(13) . . . . ?
C1 C2 C3 O1 -179.42(12) . . . . ?
C1 C2 C3 C4 1.53(19) . . . . ?
C1 C2 C12 Se1 1.76(18) . . . . ?
C1 C2 C12 N1 -179.52(13) . . . . ?
C2 C1 C9A C4A -0.04(19) . . . . ?
C2 C1 C9A C9 179.05(12) . . . . ?
C2 C3 C4 C4A -1.08(19) . . . . ?
C3 C2 C12 Se1 -177.54(10) . . . . ?
C3 C2 C12 N1 1.2(2) . . . . ?
C3 C4 C4A C4B 179.89(13) . . . . ?
C3 C4 C4A C9A 0.1(2) . . . . ?
C4 C4A C4B C5 -2.1(2) . . . . ?
C4 C4A C4B C8A 179.53(13) . . . . ?
C4 C4A C9A C1 0.51(19) . . . . ?
C4 C4A C9A C9 -178.74(12) . . . . ?
C4A C4B C5 C6 -176.87(13) . . . . ?
C4A C4B C8A C8 177.94(12) . . . . ?
C4A C4B C8A C9 -0.38(14) . . . . ?
C4B C4A C9A C1 -179.36(11) . . . . ?
C4B C4A C9A C9 1.40(14) . . . . ?
C4B C5 C6 C7 -0.8(2) . . . . ?
C4B C8A C9 C9A 1.13(13) . . . . ?
C4B C8A C9 C10 -116.84(12) . . . . ?
C4B C8A C9 C11 120.56(12) . . . . ?
C5 C4B C8A C8 -0.58(19) . . . . ?
C5 C4B C8A C9 -178.90(12) . . . . ?
C5 C6 C7 Br1 178.42(11) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C8A 1.0(2) . . . . ?
C7 C8 C8A C4B -0.57(19) . . . . ?
C7 C8 C8A C9 177.44(13) . . . . ?
C8 C8A C9 C9A -177.04(13) . . . . ?
C8 C8A C9 C10 65.00(17) . . . . ?
C8 C8A C9 C11 -57.61(17) . . . . ?
C8A C4B C5 C6 1.3(2) . . . . ?
C8A C9 C9A C1 179.32(13) . . . . ?
C8A C9 C9A C4A -1.53(13) . . . . ?
C9A C1 C2 C3 -0.96(19) . . . . ?
C9A C1 C2 C12 179.74(12) . . . . ?
C9A C4A C4B C5 177.71(13) . . . . ?
C9A C4A C4B C8A -0.62(14) . . . . ?
C10 C9 C9A C1 -62.27(17) . . . . ?
C10 C9 C9A C4A 116.88(12) . . . . ?
C11 C9 C9A C1 60.48(18) . . . . ?
C11 C9 C9A C4A -120.37(12) . . . . ?
C12 Se1 C13 C14 0.94(10) . . . . ?
C12 Se1 C13 C18 -178.52(13) . . . . ?
C12 N1 C14 C13 0.13(17) . . . . ?
C12 N1 C14 C15 179.51(13) . . . . ?
C12 C2 C3 O1 -0.10(19) . . . . ?
C12 C2 C3 C4 -179.16(12) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 N1 C12 Se1 0.68(15) . . . . ?
C14 N1 C12 C2 -178.12(12) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C13 0.5(2) . . . . ?
C18 C13 C14 N1 178.64(12) . . . . ?
C18 C13 C14 C15 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld180703_0m
_database_code_depnum_ccdc_archive 'CCDC 2018047'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-04-03
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N O2, C H2 Cl2'
_chemical_formula_sum            'C23 H18 Br Cl2 N O2'
_chemical_formula_weight         491.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7249(3)
_cell_length_b                   9.7643(3)
_cell_length_c                   13.4767(5)
_cell_angle_alpha                90.1410(10)
_cell_angle_beta                 106.2860(10)
_cell_angle_gamma                112.4560(10)
_cell_volume                     1010.68(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.680
_shelx_estimated_absorpt_T_min   0.457
_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0511 before and 0.0425 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26422
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4551
_reflns_number_total             5026
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0096(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.6413P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0560
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H20C)=Sof(H20D)=Sof(Cl3)=Sof(Cl4)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20(H20C,H20D)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
Br1 Br 0.86739(2) -0.20894(2) 0.02637(2) 0.02080(6) Uani 1 1 d . . . . .
O1 O 0.85000(15) 0.31607(12) 0.61467(8) 0.0171(2) Uani 1 1 d . . . . .
H1 H 0.834(3) 0.387(3) 0.6330(17) 0.033(6) Uiso 1 1 d . . . . .
O2 O 0.69417(13) 0.62744(11) 0.44467(7) 0.0129(2) Uani 1 1 d . . . . .
N1 N 0.75199(16) 0.54066(13) 0.59998(9) 0.0137(2) Uani 1 1 d . . . . .
C1 C 0.74691(17) 0.39984(15) 0.34150(11) 0.0121(3) Uani 1 1 d . . . . .
H1A H 0.712157 0.468059 0.300545 0.015 Uiso 1 1 calc R U . . .
C2 C 0.76941(17) 0.41132(15) 0.44963(11) 0.0118(3) Uani 1 1 d . . . . .
C3 C 0.82471(18) 0.31115(15) 0.51064(10) 0.0123(3) Uani 1 1 d . . . . .
C4 C 0.85448(18) 0.20088(15) 0.46390(11) 0.0127(3) Uani 1 1 d . . . . .
H4 H 0.892416 0.133837 0.504438 0.015 Uiso 1 1 calc R U . . .
C4A C 0.82824(17) 0.18971(15) 0.35743(11) 0.0118(3) Uani 1 1 d . . . . .
C4B C 0.84663(17) 0.08279(15) 0.29044(11) 0.0120(3) Uani 1 1 d . . . . .
C5 C 0.89317(18) -0.03699(16) 0.31423(11) 0.0141(3) Uani 1 1 d . . . . .
H5 H 0.919592 -0.059607 0.383923 0.017 Uiso 1 1 calc R U . . .
C6 C 0.90077(19) -0.12361(16) 0.23505(12) 0.0163(3) Uani 1 1 d . . . . .
H6 H 0.933518 -0.205405 0.249886 0.020 Uiso 1 1 calc R U . . .
C7 C 0.85940(18) -0.08806(16) 0.13358(12) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.81205(18) 0.03156(16) 0.10796(11) 0.0142(3) Uani 1 1 d . . . . .
H8 H 0.784202 0.053209 0.038079 0.017 Uiso 1 1 calc R U . . .
C8A C 0.80697(17) 0.11799(15) 0.18798(11) 0.0122(3) Uani 1 1 d . . . . .
C9 C 0.76057(18) 0.25380(15) 0.18200(10) 0.0121(3) Uani 1 1 d . . . . .
C9A C 0.77557(17) 0.28935(15) 0.29575(11) 0.0118(3) Uani 1 1 d . . . . .
C10 C 0.57514(19) 0.21387(17) 0.10931(11) 0.0168(3) Uani 1 1 d . . . . .
H10A H 0.570125 0.188498 0.037746 0.025 Uiso 1 1 calc R U . . .
H10B H 0.543395 0.299476 0.112433 0.025 Uiso 1 1 calc R U . . .
H10C H 0.493530 0.128154 0.131358 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8917(2) 0.38420(16) 0.14572(12) 0.0171(3) Uani 1 1 d . . . . .
H11A H 1.009716 0.407417 0.191820 0.026 Uiso 1 1 calc R U . . .
H11B H 0.863991 0.472219 0.147990 0.026 Uiso 1 1 calc R U . . .
H11C H 0.884669 0.355925 0.074251 0.026 Uiso 1 1 calc R U . . .
C12 C 0.73932(17) 0.52417(15) 0.50136(11) 0.0123(3) Uani 1 1 d . . . . .
C13 C 0.67956(18) 0.71864(15) 0.51760(11) 0.0130(3) Uani 1 1 d . . . . .
C14 C 0.71557(18) 0.66564(15) 0.61348(11) 0.0135(3) Uani 1 1 d . . . . .
C15 C 0.71326(19) 0.73822(16) 0.70179(11) 0.0160(3) Uani 1 1 d . . . . .
H15 H 0.736894 0.703550 0.767894 0.019 Uiso 1 1 calc R U . . .
C16 C 0.67473(19) 0.86380(17) 0.68856(12) 0.0177(3) Uani 1 1 d . . . . .
H16 H 0.673609 0.916915 0.747327 0.021 Uiso 1 1 calc R U . . .
C17 C 0.63767(19) 0.91407(16) 0.59150(12) 0.0171(3) Uani 1 1 d . . . . .
H17 H 0.611408 1.000160 0.585875 0.021 Uiso 1 1 calc R U . . .
C18 C 0.63811(19) 0.84131(16) 0.50237(12) 0.0162(3) Uani 1 1 d . . . . .
H18 H 0.611645 0.874110 0.435800 0.019 Uiso 1 1 calc R U . . .
C20 C 0.5565(2) 0.3015(2) 0.78503(14) 0.0284(4) Uani 1 1 d . . . . .
H20A H 0.569425 0.345222 0.720127 0.034 Uiso 0.71(4) 1 calc R U P A 1
H20B H 0.442476 0.215468 0.767298 0.034 Uiso 0.71(4) 1 calc R U P A 1
H20C H 0.436583 0.223685 0.766694 0.034 Uiso 0.29(4) 1 calc R U P A 2
H20D H 0.572686 0.347295 0.721251 0.034 Uiso 0.29(4) 1 calc R U P A 2
Cl1 Cl 0.7264(5) 0.2376(5) 0.8367(3) 0.0259(6) Uani 0.71(4) 1 d . . P A 1
Cl2 Cl 0.5602(12) 0.4346(9) 0.8729(7) 0.0306(8) Uani 0.71(4) 1 d . . P A 1
Cl3 Cl 0.698(3) 0.221(2) 0.8255(14) 0.045(2) Uani 0.29(4) 1 d . . P A 2
Cl4 Cl 0.581(3) 0.443(2) 0.8815(17) 0.029(2) Uani 0.29(4) 1 d . . 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
Br1 C7 1.8964(14) . ?
O1 H1 0.81(2) . ?
O1 C3 1.3544(17) . ?
O2 C12 1.3763(16) . ?
O2 C13 1.3884(16) . ?
N1 C12 1.3067(18) . ?
N1 C14 1.3968(18) . ?
C1 H1A 0.9500 . ?
C1 C2 1.4129(19) . ?
C1 C9A 1.3769(19) . ?
C2 C3 1.4169(19) . ?
C2 C12 1.4454(19) . ?
C3 C4 1.3877(19) . ?
C4 H4 0.9500 . ?
C4 C4A 1.3853(19) . ?
C4A C4B 1.4611(19) . ?
C4A C9A 1.4072(19) . ?
C4B C5 1.3882(19) . ?
C4B C8A 1.4035(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C7 C8 1.395(2) . ?
C8 H8 0.9500 . ?
C8 C8A 1.3885(19) . ?
C8A C9 1.5236(19) . ?
C9 C9A 1.5289(19) . ?
C9 C10 1.5351(19) . ?
C9 C11 1.540(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.391(2) . ?
C13 C18 1.378(2) . ?
C14 C15 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(2) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 Cl1 1.790(4) . ?
C20 Cl2 1.740(8) . ?
C20 Cl3 1.678(16) . ?
C20 Cl4 1.803(18) . ?

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
C3 O1 H1 107.5(15) . . ?
CL2a C20 H20A 109.2 . . ?
CL1a C20 H20A 109.2 . . ?
H20Aa C20 H20B 107.9 . . ?
C12 O2 C13 103.96(11) . . ?
C12 N1 C14 105.24(12) . . ?
C2 C1 H1A 120.1 . . ?
C9A C1 H1A 120.1 . . ?
C9A C1 C2 119.71(13) . . ?
C1 C2 C3 119.86(12) . . ?
C1 C2 C12 121.97(12) . . ?
C3 C2 C12 118.16(12) . . ?
CL1a C20 H20B 109.2 . . ?
CL2a C20 H20B 109.2 . . ?
CL4b C20 H20C 109.0 . . ?
CL3b C20 H20C 109.0 . . ?
CL3b C20 H20D 109.0 . . ?
H20Cb C20 H20D 107.8 . . ?
CL4b C20 H20D 109.0 . . ?
CL2a C20 Cl1 112.0(4) . . ?
CL3b C20 Cl4 113.0(9) . . ?
O1 C3 C2 123.12(13) . . ?
O1 C3 C4 116.92(12) . . ?
C4 C3 C2 119.96(12) . . ?
C3 C4 H4 120.4 . . ?
C4A C4 C3 119.23(13) . . ?
C4A C4 H4 120.4 . . ?
C4 C4A C4B 129.61(13) . . ?
C4 C4A C9A 121.64(13) . . ?
C9A C4A C4B 108.75(12) . . ?
C5 C4B C4A 130.48(13) . . ?
C5 C4B C8A 121.19(13) . . ?
C8A C4B C4A 108.33(12) . . ?
C4B C5 H5 120.3 . . ?
C4B C5 C6 119.39(13) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.71(13) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 Br1 118.15(11) . . ?
C6 C7 C8 122.82(13) . . ?
C8 C7 Br1 119.03(11) . . ?
C7 C8 H8 121.1 . . ?
C8A C8 C7 117.79(13) . . ?
C8A C8 H8 121.1 . . ?
C4B C8A C9 111.26(12) . . ?
C8 C8A C4B 120.09(13) . . ?
C8 C8A C9 128.64(13) . . ?
C8A C9 C9A 100.97(11) . . ?
C8A C9 C10 110.83(11) . . ?
C8A C9 C11 111.36(11) . . ?
C9A C9 C10 112.04(11) . . ?
C9A C9 C11 111.19(11) . . ?
C10 C9 C11 110.18(12) . . ?
C1 C9A C4A 119.57(13) . . ?
C1 C9A C9 129.76(12) . . ?
C4A C9A C9 110.66(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C2 119.18(12) . . ?
N1 C12 O2 114.56(12) . . ?
N1 C12 C2 126.26(13) . . ?
O2 C13 C14 107.94(12) . . ?
C18 C13 O2 128.18(13) . . ?
C18 C13 C14 123.89(13) . . ?
C13 C14 N1 108.30(12) . . ?
C13 C14 C15 120.29(13) . . ?
C15 C14 N1 131.40(14) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 C14 116.78(14) . . ?
C16 C15 H15 121.6 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.88(14) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.76(14) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 115.38(14) . . ?
C13 C18 H18 122.3 . . ?
C17 C18 H18 122.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 C8A 179.88(10) . . . . ?
O1 C3 C4 C4A 179.13(12) . . . . ?
O2 C13 C14 N1 -0.24(15) . . . . ?
O2 C13 C14 C15 178.91(12) . . . . ?
O2 C13 C18 C17 -178.34(13) . . . . ?
N1 C14 C15 C16 178.61(14) . . . . ?
C1 C2 C3 O1 179.60(13) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C12 O2 -2.7(2) . . . . ?
C1 C2 C12 N1 177.95(13) . . . . ?
C2 C1 C9A C4A -0.5(2) . . . . ?
C2 C1 C9A C9 -179.94(13) . . . . ?
C2 C3 C4 C4A -0.5(2) . . . . ?
C3 C2 C12 O2 176.71(12) . . . . ?
C3 C2 C12 N1 -2.7(2) . . . . ?
C3 C4 C4A C4B -178.54(13) . . . . ?
C3 C4 C4A C9A 1.3(2) . . . . ?
C4 C4A C4B C5 0.8(2) . . . . ?
C4 C4A C4B C8A -179.51(14) . . . . ?
C4 C4A C9A C1 -0.9(2) . . . . ?
C4 C4A C9A C9 178.70(12) . . . . ?
C4A C4B C5 C6 179.75(14) . . . . ?
C4A C4B C8A C8 -179.08(12) . . . . ?
C4A C4B C8A C9 0.43(15) . . . . ?
C4B C4A C9A C1 179.03(12) . . . . ?
C4B C4A C9A C9 -1.40(15) . . . . ?
C4B C5 C6 C7 -0.7(2) . . . . ?
C4B C8A C9 C9A -1.18(14) . . . . ?
C4B C8A C9 C10 -120.04(13) . . . . ?
C4B C8A C9 C11 116.93(13) . . . . ?
C5 C4B C8A C8 0.7(2) . . . . ?
C5 C4B C8A C9 -179.81(12) . . . . ?
C5 C6 C7 Br1 -179.16(11) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C8A 0.2(2) . . . . ?
C7 C8 C8A C4B -0.8(2) . . . . ?
C7 C8 C8A C9 179.82(13) . . . . ?
C8 C8A C9 C9A 178.28(14) . . . . ?
C8 C8A C9 C10 59.41(19) . . . . ?
C8 C8A C9 C11 -63.61(18) . . . . ?
C8A C4B C5 C6 0.1(2) . . . . ?
C8A C9 C9A C1 -178.94(14) . . . . ?
C8A C9 C9A C4A 1.55(14) . . . . ?
C9A C1 C2 C3 1.3(2) . . . . ?
C9A C1 C2 C12 -179.34(12) . . . . ?
C9A C4A C4B C5 -179.12(14) . . . . ?
C9A C4A C4B C8A 0.61(15) . . . . ?
C10 C9 C9A C1 -60.96(19) . . . . ?
C10 C9 C9A C4A 119.53(13) . . . . ?
C11 C9 C9A C1 62.83(19) . . . . ?
C11 C9 C9A C4A -116.68(13) . . . . ?
C12 O2 C13 C14 -0.26(14) . . . . ?
C12 O2 C13 C18 179.46(14) . . . . ?
C12 N1 C14 C13 0.67(15) . . . . ?
C12 N1 C14 C15 -178.35(15) . . . . ?
C12 C2 C3 O1 0.2(2) . . . . ?
C12 C2 C3 C4 179.79(12) . . . . ?
C13 O2 C12 N1 0.75(15) . . . . ?
C13 O2 C12 C2 -178.71(12) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 N1 C12 O2 -0.90(16) . . . . ?
C14 N1 C12 C2 178.52(13) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C18 C13 C14 N1 -179.98(13) . . . . ?
C18 C13 C14 C15 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goebeld180425_0ma
_database_code_depnum_ccdc_archive 'CCDC 2018045'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University Bremen
Germany
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-11-10 downloaded from the CCDC.
;
_audit_creation_date             2020-06-21
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.03.26 svn.re84ffbc8 for OlexSys, GUI svn.r6014)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N2 O4, C6 H12'
_chemical_formula_sum            'C31 H40 N2 O4'
_chemical_formula_weight         504.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   20.5800(6)
_cell_length_b                   24.0995(7)
_cell_length_c                   11.4414(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5674.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.9489.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            61897
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.205
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5628
_reflns_number_total             7040
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0048(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7040
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+2.8482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1052
_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. Uiso/Uaniso restraints and constraints
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq: with sigma of 0.008 and
sigma for terminal atoms of 0.014
3. Others
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=
 Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=
 Sof(H45A)=Sof(H45B)=1-FVAR(1)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=
 Sof(H35A)=Sof(H35B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C40(H40A,H40B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C8(H8)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
O2 O 0.77605(4) 0.47394(4) 0.40795(8) 0.0219(2) Uani 1 1 d . . . . .
O1 O 0.59627(4) 0.54879(3) 0.47297(8) 0.01892(19) Uani 1 1 d . . . . .
O4 O 0.48963(4) 0.22070(3) 0.96044(8) 0.01993(19) Uani 1 1 d . . . . .
O3 O 0.39557(4) 0.37156(4) 0.89664(8) 0.02006(19) Uani 1 1 d . . . . .
N1 N 0.71046(5) 0.54771(4) 0.37887(8) 0.0167(2) Uani 1 1 d . . . . .
N2 N 0.40084(5) 0.27378(4) 0.99080(9) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.68409(6) 0.42037(5) 0.55013(10) 0.0167(2) Uani 1 1 d . . . . .
H1A H 0.723938 0.401997 0.534027 0.020 Uiso 1 1 calc R U . . .
C2 C 0.67062(5) 0.47199(5) 0.49860(10) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.61103(5) 0.49911(5) 0.52125(10) 0.0152(2) Uani 1 1 d . . . . .
C4B C 0.54291(5) 0.39112(5) 0.73018(10) 0.0147(2) Uani 1 1 d . . . . .
C4A C 0.58068(5) 0.42449(5) 0.64747(10) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.56589(5) 0.47511(5) 0.59649(10) 0.0156(2) Uani 1 1 d . . . . .
H4 H 0.525775 0.493063 0.612550 0.019 Uiso 1 1 calc R U . . .
C5 C 0.48236(6) 0.40138(5) 0.77820(10) 0.0155(2) Uani 1 1 d . . . . .
H5 H 0.459875 0.434878 0.761482 0.019 Uiso 1 1 calc R U . . .
C6 C 0.45509(5) 0.36156(5) 0.85154(10) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.48918(6) 0.31177(5) 0.87499(10) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.55101(5) 0.30281(5) 0.82682(10) 0.0165(2) Uani 1 1 d . . . . .
H8 H 0.574197 0.269733 0.844134 0.020 Uiso 1 1 calc R U . . .
C8A C 0.57786(5) 0.34220(5) 0.75437(10) 0.0159(2) Uani 1 1 d . . . . .
C9 C 0.64249(5) 0.34119(5) 0.68916(10) 0.0174(2) Uani 1 1 d . . . . .
C9A C 0.63929(5) 0.39645(5) 0.62416(10) 0.0162(2) Uani 1 1 d . . . . .
C10 C 0.70009(6) 0.33862(6) 0.77439(13) 0.0258(3) Uani 1 1 d . . . . .
H10A H 0.740895 0.340273 0.730364 0.039 Uiso 1 1 calc R U . . .
H10B H 0.698275 0.303850 0.818688 0.039 Uiso 1 1 calc R U . . .
H10C H 0.697857 0.370092 0.828479 0.039 Uiso 1 1 calc R U . . .
C11 C 0.64591(6) 0.29243(5) 0.60268(12) 0.0245(3) Uani 1 1 d . . . . .
H11A H 0.608918 0.294305 0.548886 0.037 Uiso 1 1 calc R U . . .
H11B H 0.644483 0.257345 0.645897 0.037 Uiso 1 1 calc R U . . .
H11C H 0.686508 0.294576 0.558145 0.037 Uiso 1 1 calc R U . . .
C12 C 0.71855(5) 0.49989(5) 0.42547(10) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.81565(6) 0.51290(6) 0.34221(13) 0.0300(3) Uani 1 1 d . . . . .
H13A H 0.832585 0.495377 0.270124 0.036 Uiso 1 1 calc R U . . .
H13B H 0.852806 0.525922 0.389846 0.036 Uiso 1 1 calc R U . . .
C14 C 0.76991(5) 0.56161(5) 0.31208(10) 0.0173(2) Uani 1 1 d . . . . .
C15 C 0.75273(7) 0.56368(6) 0.18293(10) 0.0255(3) Uani 1 1 d . . . . .
H15A H 0.735239 0.527680 0.158517 0.038 Uiso 1 1 calc R U . . .
H15B H 0.791821 0.572108 0.137336 0.038 Uiso 1 1 calc R U . . .
H15C H 0.720069 0.592594 0.169665 0.038 Uiso 1 1 calc R U . . .
C16 C 0.79698(6) 0.61697(6) 0.35294(12) 0.0270(3) Uani 1 1 d . . . . .
H16A H 0.766318 0.646633 0.333138 0.041 Uiso 1 1 calc R U . . .
H16B H 0.838658 0.623983 0.314248 0.041 Uiso 1 1 calc R U . . .
H16C H 0.803406 0.615999 0.437783 0.041 Uiso 1 1 calc R U . . .
C17 C 0.45744(6) 0.26930(5) 0.94561(10) 0.0158(2) Uani 1 1 d . . . . .
C18 C 0.45031(6) 0.18948(5) 1.04373(11) 0.0210(3) Uani 1 1 d . . . . .
H18A H 0.470140 0.190284 1.122543 0.025 Uiso 1 1 calc R U . . .
H18B H 0.445551 0.150377 1.018603 0.025 Uiso 1 1 calc R U . . .
C19 C 0.38412(6) 0.21926(5) 1.04365(10) 0.0175(2) Uani 1 1 d . . . . .
C20 C 0.33519(6) 0.19028(5) 0.96464(11) 0.0248(3) Uani 1 1 d . . . . .
H20A H 0.296278 0.213425 0.956845 0.037 Uiso 1 1 calc R U . . .
H20B H 0.323243 0.154419 0.998846 0.037 Uiso 1 1 calc R U . . .
H20C H 0.354555 0.184339 0.887399 0.037 Uiso 1 1 calc R U . . .
C21 C 0.35740(6) 0.22727(5) 1.16624(11) 0.0239(3) Uani 1 1 d . . . . .
H21A H 0.388463 0.248731 1.212840 0.036 Uiso 1 1 calc R U . . .
H21B H 0.350493 0.190977 1.202804 0.036 Uiso 1 1 calc R U . . .
H21C H 0.316006 0.247279 1.162156 0.036 Uiso 1 1 calc R U . . .
C30 C 0.40822(12) 0.54242(8) 0.8190(2) 0.0332(5) Uani 0.794(4) 1 d . . P A 1
H30A H 0.420196 0.526792 0.741931 0.040 Uiso 0.794(4) 1 calc R U P A 1
H30B H 0.384657 0.513420 0.863257 0.040 Uiso 0.794(4) 1 calc R U P A 1
C31 C 0.46976(15) 0.55844(9) 0.8852(2) 0.0368(6) Uani 0.794(4) 1 d . . P A 1
H31A H 0.458181 0.569366 0.965920 0.044 Uiso 0.794(4) 1 calc R U P A 1
H31B H 0.499030 0.525912 0.889657 0.044 Uiso 0.794(4) 1 calc R U P A 1
C32 C 0.50507(11) 0.60609(11) 0.8259(3) 0.0331(6) Uani 0.794(4) 1 d . . P A 1
H32A H 0.522150 0.593421 0.749521 0.040 Uiso 0.794(4) 1 calc R U P A 1
H32B H 0.542436 0.617558 0.874723 0.040 Uiso 0.794(4) 1 calc R U P A 1
C33 C 0.46026(10) 0.65577(8) 0.80688(17) 0.0318(5) Uani 0.794(4) 1 d . . P A 1
H33A H 0.447473 0.671370 0.883548 0.038 Uiso 0.794(4) 1 calc R U P A 1
H33B H 0.483844 0.684911 0.763082 0.038 Uiso 0.794(4) 1 calc R U P A 1
C34 C 0.39961(11) 0.63910(9) 0.73932(19) 0.0317(5) Uani 0.794(4) 1 d . . P A 1
H34A H 0.370430 0.671554 0.731704 0.038 Uiso 0.794(4) 1 calc R U P A 1
H34B H 0.412024 0.626905 0.659768 0.038 Uiso 0.794(4) 1 calc R U P A 1
C35 C 0.36389(12) 0.59230(11) 0.8014(3) 0.0304(6) Uani 0.794(4) 1 d . . P A 1
H35A H 0.325650 0.581100 0.754456 0.037 Uiso 0.794(4) 1 calc R U P A 1
H35B H 0.348162 0.605554 0.878228 0.037 Uiso 0.794(4) 1 calc R U P A 1
C40 C 0.3784(5) 0.6106(5) 0.7686(9) 0.033(2) Uani 0.206(4) 1 d . U P A 2
H40A H 0.371124 0.644280 0.816286 0.040 Uiso 0.206(4) 1 calc R U P A 2
H40B H 0.341436 0.606769 0.713779 0.040 Uiso 0.206(4) 1 calc R U P A 2
C41 C 0.3810(5) 0.5607(5) 0.8471(9) 0.046(2) Uani 0.206(4) 1 d . U P A 2
H41A H 0.386295 0.526749 0.799392 0.055 Uiso 0.206(4) 1 calc R U P A 2
H41B H 0.339697 0.557539 0.891053 0.055 Uiso 0.206(4) 1 calc R U P A 2
C42 C 0.4377(6) 0.5658(5) 0.9328(9) 0.054(3) Uani 0.206(4) 1 d . U P A 2
H42A H 0.429991 0.597324 0.986508 0.065 Uiso 0.206(4) 1 calc R U P A 2
H42B H 0.441040 0.531512 0.980140 0.065 Uiso 0.206(4) 1 calc R U P A 2
C43 C 0.5007(5) 0.5750(6) 0.8655(9) 0.042(2) Uani 0.206(4) 1 d . U P A 2
H43A H 0.536523 0.581790 0.921569 0.050 Uiso 0.206(4) 1 calc R U P A 2
H43B H 0.511396 0.541051 0.820659 0.050 Uiso 0.206(4) 1 calc R U P A 2
C44 C 0.4957(6) 0.6223(7) 0.7849(12) 0.060(4) Uani 0.206(4) 1 d . U P A 2
H44A H 0.536877 0.625760 0.740756 0.072 Uiso 0.206(4) 1 calc R U P A 2
H44B H 0.489811 0.656723 0.830866 0.072 Uiso 0.206(4) 1 calc R U P A 2
C45 C 0.4406(5) 0.6169(5) 0.7000(9) 0.056(3) Uani 0.206(4) 1 d . U P A 2
H45A H 0.447356 0.584156 0.649232 0.067 Uiso 0.206(4) 1 calc R U P A 2
H45B H 0.438267 0.650337 0.649765 0.067 Uiso 0.206(4) 1 calc R U P A 2
H3 H 0.3843(9) 0.3400(8) 0.9410(17) 0.052(5) Uiso 1 1 d . . . . .
H1 H 0.6315(10) 0.5599(8) 0.4301(17) 0.054(6) 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
O2 C12 1.3534(14) . ?
O2 C13 1.4531(15) . ?
C30a H30A 0.9900 . ?
C30a H30B 0.9900 . ?
C30a C31 1.525(3) . ?
C31a H31A 0.9900 . ?
C31a H31B 0.9900 . ?
C31a C32 1.519(4) . ?
C32a H32A 0.9900 . ?
C32a H32B 0.9900 . ?
C32a C33 1.527(3) . ?
C33a H33A 0.9900 . ?
C33a H33B 0.9900 . ?
C33a C34 1.522(3) . ?
C34a H34A 0.9900 . ?
C34a H34B 0.9900 . ?
C30a C35 1.522(3) . ?
C34a C35 1.522(3) . ?
C35a H35A 0.9900 . ?
C35a H35B 0.9900 . ?
C40b H40A 0.9900 . ?
C40b H40B 0.9900 . ?
C40b C41 1.502(14) . ?
C41b H41A 0.9900 . ?
C41b H41B 0.9900 . ?
C41b C42 1.529(14) . ?
C42b H42A 0.9900 . ?
C42b H42B 0.9900 . ?
C42b C43 1.525(14) . ?
C43b H43A 0.9900 . ?
C43b H43B 0.9900 . ?
C43b C44 1.471(15) . ?
C44b H44A 0.9900 . ?
C44b H44B 0.9900 . ?
C40b C45 1.510(14) . ?
C44b C45 1.498(14) . ?
C45b H45A 0.9900 . ?
C45b H45B 0.9900 . ?
O1 C3 1.3530(14) . ?
O1 H1 0.92(2) . ?
O4 C17 1.3562(14) . ?
O4 C18 1.4592(14) . ?
O3 C6 1.3509(14) . ?
O3 H3 0.94(2) . ?
N1 C12 1.2806(15) . ?
N1 C14 1.4809(14) . ?
N2 C17 1.2791(15) . ?
N2 C19 1.4866(14) . ?
C1 H1A 0.9500 . ?
C1 C2 1.4043(16) . ?
C1 C9A 1.3783(16) . ?
C2 C3 1.4137(16) . ?
C2 C12 1.4579(16) . ?
C3 C4 1.3923(16) . ?
C4B C4A 1.4650(15) . ?
C4B C5 1.3841(16) . ?
C4B C8A 1.4085(16) . ?
C4A C4 1.3860(16) . ?
C4A C9A 1.4081(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3928(16) . ?
C6 C7 1.4156(16) . ?
C7 C8 1.4034(16) . ?
C7 C17 1.4584(15) . ?
C8 H8 0.9500 . ?
C8 C8A 1.3761(16) . ?
C8A C9 1.5251(16) . ?
C9 C9A 1.5266(16) . ?
C9 C10 1.5363(17) . ?
C9 C11 1.5378(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5437(17) . ?
C14 C15 1.5202(16) . ?
C14 C16 1.5195(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5396(17) . ?
C19 C20 1.5229(17) . ?
C19 C21 1.5189(17) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 105.58(9) . . ?
C32a C31a C30 111.54(18) . . ?
C3 O1 H1 107.4(12) . . ?
C17 O4 C18 104.85(9) . . ?
C6 O3 H3 106.5(12) . . ?
C34a C35a C30 110.9(2) . . ?
C35a C30a H30A 109.4 . . ?
C12 N1 C14 108.13(10) . . ?
C17 N2 C19 107.50(9) . . ?
C2 C1 H1A 120.1 . . ?
C9A C1 H1A 120.1 . . ?
C9A C1 C2 119.76(11) . . ?
C1 C2 C3 120.26(10) . . ?
C1 C2 C12 121.06(10) . . ?
C31a C30a H30A 109.4 . . ?
C35a C30a H30B 109.4 . . ?
C31a C30a H30B 109.4 . . ?
H30Aa C30a H30B 108.0 . . ?
C35a C30a C31 111.32(17) . . ?
C32a C31a H31A 109.3 . . ?
C30a C31a H31A 109.3 . . ?
H31Aa C31a H31B 108.0 . . ?
C30a C31a H31B 109.3 . . ?
C32a C31a H31B 109.3 . . ?
C34a C33a C32 111.14(17) . . ?
C31a C32a H32A 109.3 . . ?
C33a C32a H32A 109.3 . . ?
H32Aa C32a H32B 108.0 . . ?
C33a C32a H32B 109.3 . . ?
C3 C2 C12 118.61(10) . . ?
O1 C3 C2 121.94(10) . . ?
O1 C3 C4 118.05(10) . . ?
C4 C3 C2 120.00(10) . . ?
C5 C4B C4A 129.50(10) . . ?
C5 C4B C8A 122.09(10) . . ?
C8A C4B C4A 108.39(10) . . ?
C4 C4A C4B 129.68(11) . . ?
C4 C4A C9A 122.06(10) . . ?
C9A C4A C4B 108.26(10) . . ?
C3 C4 H4 120.7 . . ?
C31a C32a H32B 109.3 . . ?
C35a C34a C33 110.78(18) . . ?
C31a C32a C33 111.56(19) . . ?
C32a C33a H33A 109.4 . . ?
C34a C33a H33A 109.4 . . ?
C32a C33a H33B 109.4 . . ?
C34a C33a H33B 109.4 . . ?
H33Aa C33a H33B 108.0 . . ?
C35a C34a H34A 109.5 . . ?
C33a C34a H34A 109.5 . . ?
C35a C34a H34B 109.5 . . ?
H34Aa C34a H34B 108.1 . . ?
C33a C34a H34B 109.5 . . ?
C34a C35a H35A 109.5 . . ?
C30a C35a H35A 109.5 . . ?
C34a C35a H35B 109.5 . . ?
H35Aa C35a H35B 108.0 . . ?
C30a C35a H35B 109.5 . . ?
C44b C45b C40 108.3(9) . . ?
C41b C40b H40A 109.4 . . ?
C45b C40b H40A 109.4 . . ?
H40Ab C40b H40B 108.0 . . ?
C45b C40b H40B 109.4 . . ?
C41b C40b H40B 109.4 . . ?
C4A C4 C3 118.64(10) . . ?
C4A C4 H4 120.7 . . ?
C4B C5 H5 120.7 . . ?
C4B C5 C6 118.62(10) . . ?
C6 C5 H5 120.7 . . ?
O3 C6 C5 118.20(10) . . ?
O3 C6 C7 121.89(10) . . ?
C5 C6 C7 119.90(10) . . ?
C6 C7 C17 118.55(10) . . ?
C8 C7 C6 120.36(10) . . ?
C8 C7 C17 121.04(10) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 C7 119.64(10) . . ?
C8A C8 H8 120.2 . . ?
C4B C8A C9 111.25(10) . . ?
C8 C8A C4B 119.39(10) . . ?
C8 C8A C9 129.34(10) . . ?
C8A C9 C9A 100.76(9) . . ?
C8A C9 C10 111.29(10) . . ?
C8A C9 C11 111.52(10) . . ?
C9A C9 C10 112.19(10) . . ?
C9A C9 C11 110.79(10) . . ?
C10 C9 C11 110.01(10) . . ?
C1 C9A C4A 119.25(10) . . ?
C1 C9A C9 129.44(10) . . ?
C4A C9A C9 111.31(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C2 117.61(10) . . ?
N1 C12 O2 117.89(10) . . ?
N1 C12 C2 124.48(11) . . ?
O2 C13 H13A 110.7 . . ?
O2 C13 H13B 110.7 . . ?
O2 C13 C14 105.36(10) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
N1 C14 C13 102.50(9) . . ?
N1 C14 C15 108.48(10) . . ?
N1 C14 C16 110.04(10) . . ?
C15 C14 C13 112.58(11) . . ?
C16 C14 C13 112.05(11) . . ?
C16 C14 C15 110.82(10) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C7 117.17(10) . . ?
N2 C17 O4 117.84(10) . . ?
N2 C17 C7 124.94(10) . . ?
O4 C18 H18A 110.9 . . ?
O4 C18 H18B 110.9 . . ?
O4 C18 C19 104.47(9) . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
N2 C19 C18 101.98(9) . . ?
N2 C19 C20 108.48(10) . . ?
N2 C19 C21 110.31(10) . . ?
C20 C19 C18 111.81(10) . . ?
C21 C19 C18 112.27(10) . . ?
C21 C19 C20 111.53(10) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C43b C42b C41 109.7(8) . . ?
C42b C41b H41A 109.6 . . ?
C40b C41b H41A 109.6 . . ?
C40b C41b H41B 109.6 . . ?
H41Ab C41b H41B 108.1 . . ?
C42b C41b H41B 109.6 . . ?
C44b C43b C42 111.7(10) . . ?
C40b C41b C42 110.3(8) . . ?
C41b C42b H42A 109.7 . . ?
C43b C42b H42A 109.7 . . ?
H42Ab C42b H42B 108.2 . . ?
C43b C42b H42B 109.7 . . ?
C41b C42b H42B 109.7 . . ?
C42b C43b H43A 109.3 . . ?
C44b C43b H43A 109.3 . . ?
C44b C43b H43B 109.3 . . ?
C42b C43b H43B 109.3 . . ?
H43Ab C43b H43B 107.9 . . ?
C45b C44b H44A 108.9 . . ?
C43b C44b H44A 108.9 . . ?
C45b C44b H44B 108.9 . . ?
H44Ab C44b H44B 107.8 . . ?
C43b C44b H44B 108.9 . . ?
C41b C40b C45 111.3(8) . . ?
C43b C44b C45 113.2(10) . . ?
C40b C45b H45A 110.0 . . ?
C44b C45b H45A 110.0 . . ?
C40b C45b H45B 110.0 . . ?
C44b C45b H45B 110.0 . . ?
H45Ab C45b H45B 108.4 . . ?

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
C40b C41b C42b C43b -55.1(13) . . . . ?
C31a C32a C33a C34a -55.0(3) . . . . ?
C35a C30a C31a C32a -54.5(3) . . . . ?
C41b C40b C45b C44b -58.7(13) . . . . ?
C33a C34a C35a C30a -56.9(3) . . . . ?
C45b C40b C41b C42b 59.2(12) . . . . ?
C30a C31a C32a C33a 54.0(3) . . . . ?
C43b C44b C45b C40b 57.6(16) . . . . ?
C32a C33a C34a C35a 56.3(3) . . . . ?
C41b C42b C43b C44b 53.6(13) . . . . ?
C31a C30a C35a C34a 56.0(3) . . . . ?
C42b C43b C44b C45b -56.3(15) . . . . ?
O2 C13 C14 N1 7.19(13) . . . . ?
O2 C13 C14 C15 -109.16(12) . . . . ?
O2 C13 C14 C16 125.13(11) . . . . ?
O1 C3 C4 C4A -179.35(10) . . . . ?
O4 C18 C19 N2 -17.86(12) . . . . ?
O4 C18 C19 C20 97.85(11) . . . . ?
O4 C18 C19 C21 -135.91(10) . . . . ?
O3 C6 C7 C8 -179.88(10) . . . . ?
O3 C6 C7 C17 2.82(16) . . . . ?
C1 C2 C3 O1 -179.83(10) . . . . ?
C1 C2 C3 C4 1.12(17) . . . . ?
C1 C2 C12 O2 0.80(16) . . . . ?
C1 C2 C12 N1 -177.63(11) . . . . ?
C2 C1 C9A C4A -0.39(17) . . . . ?
C2 C1 C9A C9 179.49(11) . . . . ?
C2 C3 C4 C4A -0.26(16) . . . . ?
C3 C2 C12 O2 177.96(10) . . . . ?
C3 C2 C12 N1 -0.46(17) . . . . ?
C4B C4A C4 C3 178.85(11) . . . . ?
C4B C4A C9A C1 -178.55(10) . . . . ?
C4B C4A C9A C9 1.55(13) . . . . ?
C4B C5 C6 O3 -179.04(10) . . . . ?
C4B C5 C6 C7 -0.31(16) . . . . ?
C4B C8A C9 C9A -0.13(12) . . . . ?
C4B C8A C9 C10 119.00(11) . . . . ?
C4B C8A C9 C11 -117.74(11) . . . . ?
C4A C4B C5 C6 177.04(11) . . . . ?
C4A C4B C8A C8 -177.44(10) . . . . ?
C4A C4B C8A C9 1.04(13) . . . . ?
C4 C4A C9A C1 1.27(17) . . . . ?
C4 C4A C9A C9 -178.63(10) . . . . ?
C5 C4B C4A C4 0.5(2) . . . . ?
C5 C4B C4A C9A -179.67(11) . . . . ?
C5 C4B C8A C8 0.81(17) . . . . ?
C5 C4B C8A C9 179.29(10) . . . . ?
C5 C6 C7 C8 1.44(17) . . . . ?
C5 C6 C7 C17 -175.86(10) . . . . ?
C6 C7 C8 C8A -1.44(17) . . . . ?
C6 C7 C17 O4 175.97(10) . . . . ?
C6 C7 C17 N2 -1.42(17) . . . . ?
C7 C8 C8A C4B 0.34(17) . . . . ?
C7 C8 C8A C9 -177.84(11) . . . . ?
C8 C7 C17 O4 -1.31(16) . . . . ?
C8 C7 C17 N2 -178.69(11) . . . . ?
C8 C8A C9 C9A 178.16(12) . . . . ?
C8 C8A C9 C10 -62.71(16) . . . . ?
C8 C8A C9 C11 60.55(16) . . . . ?
C8A C4B C4A C4 178.60(11) . . . . ?
C8A C4B C4A C9A -1.60(13) . . . . ?
C8A C4B C5 C6 -0.81(17) . . . . ?
C8A C9 C9A C1 179.23(12) . . . . ?
C8A C9 C9A C4A -0.88(12) . . . . ?
C9A C1 C2 C3 -0.78(17) . . . . ?
C9A C1 C2 C12 176.34(11) . . . . ?
C9A C4A C4 C3 -0.94(17) . . . . ?
C10 C9 C9A C1 60.76(16) . . . . ?
C10 C9 C9A C4A -119.35(11) . . . . ?
C11 C9 C9A C1 -62.62(16) . . . . ?
C11 C9 C9A C4A 117.26(11) . . . . ?
C12 O2 C13 C14 -6.63(13) . . . . ?
C12 N1 C14 C13 -5.31(13) . . . . ?
C12 N1 C14 C15 113.95(11) . . . . ?
C12 N1 C14 C16 -124.66(11) . . . . ?
C12 C2 C3 O1 2.98(16) . . . . ?
C12 C2 C3 C4 -176.07(10) . . . . ?
C13 O2 C12 N1 3.64(14) . . . . ?
C13 O2 C12 C2 -174.89(11) . . . . ?
C14 N1 C12 O2 1.32(14) . . . . ?
C14 N1 C12 C2 179.75(10) . . . . ?
C17 O4 C18 C19 16.21(12) . . . . ?
C17 N2 C19 C18 13.50(12) . . . . ?
C17 N2 C19 C20 -104.62(11) . . . . ?
C17 N2 C19 C21 132.95(10) . . . . ?
C17 C7 C8 C8A 175.79(10) . . . . ?
C18 O4 C17 N2 -8.52(14) . . . . ?
C18 O4 C17 C7 173.90(10) . . . . ?
C19 N2 C17 O4 -3.76(14) . . . . ?
C19 N2 C17 C7 173.61(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
