# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

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

data_40161
_database_code_depnum_ccdc_archive 'CCDC 1901554'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

# Crystallographer: Thibault Cheisson

_audit_creation_date             2017-08-21
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C33 H49 N4 O3, C2 H6 O, Cl'
_chemical_formula_sum            'C35 H55 Cl N4 O4'
_chemical_formula_weight         631.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   16.6055(10)
_cell_length_b                   19.9177(14)
_cell_length_c                   21.7032(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7178.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9178
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       prism
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            80007
_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         27.539
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                6622
_reflns_number_total             8265
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         8265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.017
_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)+(0.0406P)²+3.3610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0944
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct

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 0.22257(6) 0.31547(5) 0.26310(5) 0.0305(2) Uani 1 1 d . . . . .
H1 H 0.2450 0.2779 0.2590 0.046 Uiso 1 1 d R . . . .
O2 O -0.06812(6) 0.20628(4) 0.45606(4) 0.0235(2) Uani 1 1 d . . . . .
H2 H -0.0958 0.2348 0.4370 0.035 Uiso 1 1 d R . . . .
O3 O -0.11768(5) 0.07911(4) 0.15411(4) 0.0195(2) Uani 1 1 d . . . . .
H3 H -0.1500 0.0999 0.1769 0.029 Uiso 1 1 d R . . . .
N1 N 0.14956(6) 0.30788(5) 0.29919(5) 0.0189(2) Uani 1 1 d . . . . .
N2 N -0.06614(6) 0.14409(5) 0.42120(5) 0.0174(2) Uani 1 1 d . . . . .
N3 N -0.04540(6) 0.11929(5) 0.14513(5) 0.0158(2) Uani 1 1 d . . . . .
N4 N 0.00924(6) 0.16443(5) 0.26229(4) 0.0117(2) Uani 1 1 d . . . . .
H4 H -0.0365 0.1681 0.2325 0.014 Uiso 1 1 d R . . . .
C1 C 0.00837(7) 0.22789(6) 0.30054(6) 0.0139(2) Uani 1 1 d . . . . .
H1a H -0.0417 0.2291 0.3253 0.017 Uiso 1 1 calc R . . . .
H1b H 0.0545 0.2270 0.3295 0.017 Uiso 1 1 calc R . . . .
C2 C 0.01318(7) 0.29071(6) 0.26193(6) 0.0147(2) Uani 1 1 d . . . . .
C3 C -0.05346(8) 0.31137(6) 0.22771(6) 0.0207(3) Uani 1 1 d . . . . .
H3a H -0.1018 0.2859 0.2293 0.025 Uiso 1 1 calc R . . . .
C4 C -0.04991(9) 0.36852(7) 0.19153(7) 0.0269(3) Uani 1 1 d . . . . .
H4a H -0.0957 0.3825 0.1686 0.032 Uiso 1 1 calc R . . . .
C5 C 0.02086(9) 0.40523(7) 0.18897(7) 0.0278(3) Uani 1 1 d . . . . .
H5a H 0.0239 0.4439 0.1634 0.033 Uiso 1 1 calc R . . . .
C6 C 0.08698(9) 0.38619(6) 0.22323(7) 0.0245(3) Uani 1 1 d . . . . .
H6a H 0.1352 0.4117 0.2210 0.029 Uiso 1 1 calc R . . . .
C7 C 0.08355(8) 0.32959(6) 0.26116(6) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.16120(8) 0.34618(7) 0.35822(7) 0.0256(3) Uani 1 1 d . . . . .
C9 C 0.22604(10) 0.30841(8) 0.39356(9) 0.0412(4) Uani 1 1 d . . . . .
H9a H 0.2107 0.2611 0.3973 0.062 Uiso 1 1 calc GR . . . .
H9b H 0.2319 0.3280 0.4348 0.062 Uiso 1 1 calc GR . . . .
H9c H 0.2773 0.3119 0.3714 0.062 Uiso 1 1 calc GR . . . .
C10 C 0.08248(9) 0.34419(7) 0.39448(7) 0.0288(3) Uani 1 1 d . . . . .
H10a H 0.0394 0.3643 0.3698 0.043 Uiso 1 1 calc GR . . . .
H10b H 0.0888 0.3695 0.4329 0.043 Uiso 1 1 calc GR . . . .
H10c H 0.0687 0.2975 0.4040 0.043 Uiso 1 1 calc GR . . . .
C11 C 0.18735(10) 0.41913(7) 0.34804(9) 0.0373(4) Uani 1 1 d . . . . .
H11a H 0.2348 0.4202 0.3212 0.056 Uiso 1 1 calc GR . . . .
H11b H 0.2006 0.4397 0.3878 0.056 Uiso 1 1 calc GR . . . .
H11c H 0.1434 0.4442 0.3286 0.056 Uiso 1 1 calc GR . . . .
C12 C -0.00822(7) 0.10365(6) 0.30299(5) 0.0137(2) Uani 1 1 d . . . . .
H12a H -0.0653 0.1051 0.3162 0.016 Uiso 1 1 calc R . . . .
H12b H -0.0003 0.0622 0.2786 0.016 Uiso 1 1 calc R . . . .
C13 C 0.04491(7) 0.10103(6) 0.35925(6) 0.0156(2) Uani 1 1 d . . . . .
C14 C 0.12427(8) 0.07789(6) 0.35445(6) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.1421 0.0585 0.3168 0.024 Uiso 1 1 calc R . . . .
C15 C 0.17732(8) 0.08269(7) 0.40353(7) 0.0235(3) Uani 1 1 d . . . . .
H15 H 0.2311 0.0669 0.3996 0.028 Uiso 1 1 calc R . . . .
C16 C 0.15115(8) 0.11073(7) 0.45832(7) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.1879 0.1162 0.4915 0.030 Uiso 1 1 calc R . . . .
C17 C 0.07167(8) 0.13093(7) 0.46518(6) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.0541 0.1490 0.5034 0.027 Uiso 1 1 calc R . . . .
C18 C 0.01751(8) 0.12485(6) 0.41644(6) 0.0168(3) Uani 1 1 d . . . . .
C19 C -0.12087(8) 0.09459(6) 0.45303(6) 0.0204(3) Uani 1 1 d . . . . .
C20 C -0.20652(8) 0.12095(7) 0.44444(7) 0.0264(3) Uani 1 1 d . . . . .
H20a H -0.2121 0.1642 0.4655 0.040 Uiso 1 1 calc GR . . . .
H20b H -0.2449 0.0888 0.4619 0.040 Uiso 1 1 calc GR . . . .
H20c H -0.2175 0.1268 0.4004 0.040 Uiso 1 1 calc GR . . . .
C21 C -0.11329(9) 0.02712(7) 0.42031(7) 0.0252(3) Uani 1 1 d . . . . .
H21a H -0.1248 0.0329 0.3763 0.038 Uiso 1 1 calc GR . . . .
H21b H -0.1518 -0.0048 0.4381 0.038 Uiso 1 1 calc GR . . . .
H21c H -0.0584 0.0098 0.4254 0.038 Uiso 1 1 calc GR . . . .
C22 C -0.10157(9) 0.08607(7) 0.52176(6) 0.0281(3) Uani 1 1 d . . . . .
H22a H -0.0486 0.0650 0.5263 0.042 Uiso 1 1 calc GR . . . .
H22b H -0.1426 0.0576 0.5410 0.042 Uiso 1 1 calc GR . . . .
H22c H -0.1011 0.1302 0.5418 0.042 Uiso 1 1 calc GR . . . .
C23 C 0.08517(7) 0.15957(6) 0.22435(6) 0.0144(2) Uani 1 1 d . . . . .
H23a H 0.1325 0.1612 0.2520 0.017 Uiso 1 1 calc R . . . .
H23b H 0.0882 0.1985 0.1961 0.017 Uiso 1 1 calc R . . . .
C24 C 0.08759(7) 0.09555(6) 0.18721(6) 0.0155(2) Uani 1 1 d . . . . .
C25 C 0.15582(8) 0.05505(7) 0.19126(6) 0.0213(3) Uani 1 1 d . . . . .
H25 H 0.2015 0.0705 0.2135 0.026 Uiso 1 1 calc R . . . .
C26 C 0.15776(9) -0.00735(7) 0.16329(8) 0.0304(3) Uani 1 1 d . . . . .
H26 H 0.2049 -0.0343 0.1656 0.036 Uiso 1 1 calc R . . . .
C27 C 0.09045(9) -0.03043(7) 0.13182(8) 0.0311(3) Uani 1 1 d . . . . .
H27 H 0.0905 -0.0742 0.1145 0.037 Uiso 1 1 calc R . . . .
C28 C 0.02332(8) 0.01010(7) 0.12556(7) 0.0235(3) Uani 1 1 d . . . . .
H28 H -0.0223 -0.0058 0.1035 0.028 Uiso 1 1 calc R . . . .
C29 C 0.02228(7) 0.07411(6) 0.15142(6) 0.0167(2) Uani 1 1 d . . . . .
C30 C -0.05211(8) 0.15325(7) 0.08307(6) 0.0203(3) Uani 1 1 d . . . . .
C31 C -0.12441(8) 0.20013(7) 0.08691(7) 0.0255(3) Uani 1 1 d . . . . .
H31a H -0.1739 0.1735 0.0896 0.038 Uiso 1 1 calc GR . . . .
H31b H -0.1263 0.2285 0.0500 0.038 Uiso 1 1 calc GR . . . .
H31c H -0.1195 0.2286 0.1236 0.038 Uiso 1 1 calc GR . . . .
C32 C -0.06311(10) 0.10435(8) 0.02945(7) 0.0325(3) Uani 1 1 d . . . . .
H32a H -0.0140 0.0777 0.0243 0.049 Uiso 1 1 calc GR . . . .
H32b H -0.0738 0.1296 -0.0084 0.049 Uiso 1 1 calc GR . . . .
H32c H -0.1086 0.0744 0.0381 0.049 Uiso 1 1 calc GR . . . .
C33 C 0.02415(9) 0.19495(8) 0.07360(7) 0.0270(3) Uani 1 1 d . . . . .
H33a H 0.0286 0.2284 0.1066 0.040 Uiso 1 1 calc GR . . . .
H33b H 0.0214 0.2178 0.0337 0.040 Uiso 1 1 calc GR . . . .
H33c H 0.0713 0.1654 0.0745 0.040 Uiso 1 1 calc GR . . . .
O4 O 0.33718(6) 0.27384(5) 0.12654(5) 0.0259(2) Uani 1 1 d . . . . .
H4b H 0.3238 0.2473 0.1548 0.039 Uiso 1 1 d R . . . .
C34 C 0.19576(9) 0.28966(8) 0.10078(8) 0.0336(4) Uani 1 1 d . . . . .
H34a H 0.2007 0.2671 0.0608 0.050 Uiso 1 1 calc GR . . . .
H34b H 0.1538 0.3242 0.0984 0.050 Uiso 1 1 calc GR . . . .
H34c H 0.1812 0.2567 0.1324 0.050 Uiso 1 1 calc GR . . . .
C35 C 0.27494(8) 0.32191(7) 0.11734(7) 0.0252(3) Uani 1 1 d . . . . .
H35a H 0.2910 0.3530 0.0840 0.030 Uiso 1 1 calc R . . . .
H35b H 0.2681 0.3486 0.1555 0.030 Uiso 1 1 calc R . . . .
Cl1 Cl 0.30660(2) 0.17433(2) 0.24389(2) 0.01866(8) Uani 1 1 d . . . . .


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 N1 1.4513(14) . ?
O2 N2 1.4519(13) . ?
O3 N3 1.4557(12) . ?
N1 C7 1.4388(17) . ?
N1 C8 1.5034(18) . ?
N2 C18 1.4446(16) . ?
N2 C19 1.5084(16) . ?
N3 C29 1.4463(16) . ?
N3 C30 1.5111(16) . ?
N4 C1 1.5123(14) . ?
N4 C12 1.5263(14) . ?
N4 C23 1.5090(15) . ?
C1 C2 1.5082(16) . ?
C2 C3 1.3949(18) . ?
C2 C7 1.4017(17) . ?
C3 C4 1.3841(18) . ?
C4 C5 1.385(2) . ?
C5 C6 1.379(2) . ?
C6 C7 1.3971(18) . ?
C8 C9 1.521(2) . ?
C8 C10 1.526(2) . ?
C8 C11 1.532(2) . ?
C12 C13 1.5073(17) . ?
C13 C14 1.4000(18) . ?
C13 C18 1.4045(18) . ?
C14 C15 1.3857(19) . ?
C15 C16 1.384(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.3936(18) . ?
C19 C20 1.5274(19) . ?
C19 C21 1.5253(18) . ?
C19 C22 1.5351(19) . ?
C23 C24 1.5091(16) . ?
C24 C25 1.3936(17) . ?
C24 C29 1.4006(17) . ?
C25 C26 1.3835(18) . ?
C26 C27 1.388(2) . ?
C27 C28 1.383(2) . ?
C28 C29 1.3931(17) . ?
C30 C31 1.5232(19) . ?
C30 C32 1.5286(19) . ?
C30 C33 1.5282(18) . ?
O4 C35 1.4229(16) . ?
C34 C35 1.507(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C8 107.44(10) . . ?
C7 N1 O1 107.18(10) . . ?
C7 N1 C8 115.74(10) . . ?
O2 N2 C19 107.77(9) . . ?
C18 N2 O2 106.58(9) . . ?
C18 N2 C19 116.03(10) . . ?
O3 N3 C30 107.74(9) . . ?
C29 N3 O3 106.62(9) . . ?
C29 N3 C30 114.83(10) . . ?
C1 N4 C12 110.08(9) . . ?
C23 N4 C1 111.17(9) . . ?
C23 N4 C12 115.07(9) . . ?
C2 C1 N4 112.82(10) . . ?
C3 C2 C1 119.90(11) . . ?
C3 C2 C7 119.48(11) . . ?
C7 C2 C1 120.60(11) . . ?
C4 C3 C2 120.72(12) . . ?
C3 C4 C5 119.54(13) . . ?
C6 C5 C4 120.57(12) . . ?
C5 C6 C7 120.46(12) . . ?
C2 C7 N1 117.53(11) . . ?
C6 C7 N1 123.33(12) . . ?
C6 C7 C2 119.13(12) . . ?
N1 C8 C9 105.64(11) . . ?
N1 C8 C10 108.43(11) . . ?
N1 C8 C11 113.25(13) . . ?
C9 C8 C10 109.47(14) . . ?
C9 C8 C11 109.94(12) . . ?
C10 C8 C11 109.98(12) . . ?
C13 C12 N4 112.65(9) . . ?
C14 C13 C12 120.13(11) . . ?
C14 C13 C18 118.81(12) . . ?
C18 C13 C12 120.97(11) . . ?
C15 C14 C13 121.23(13) . . ?
C16 C15 C14 119.27(13) . . ?
C15 C16 C17 120.52(13) . . ?
C16 C17 C18 120.47(13) . . ?
C13 C18 N2 117.65(11) . . ?
C17 C18 N2 122.91(12) . . ?
C17 C18 C13 119.41(12) . . ?
N2 C19 C20 106.29(10) . . ?
N2 C19 C21 108.23(10) . . ?
N2 C19 C22 113.05(11) . . ?
C20 C19 C22 110.55(11) . . ?
C21 C19 C20 108.84(12) . . ?
C21 C19 C22 109.74(11) . . ?
N4 C23 C24 111.59(9) . . ?
C25 C24 C23 118.50(11) . . ?
C25 C24 C29 119.21(11) . . ?
C29 C24 C23 122.22(11) . . ?
C26 C25 C24 120.74(12) . . ?
C25 C26 C27 119.64(13) . . ?
C28 C27 C26 120.27(12) . . ?
C27 C28 C29 120.30(12) . . ?
C24 C29 N3 117.67(10) . . ?
C28 C29 N3 122.75(11) . . ?
C28 C29 C24 119.53(12) . . ?
N3 C30 C31 106.49(10) . . ?
N3 C30 C32 113.71(11) . . ?
N3 C30 C33 107.58(10) . . ?
C31 C30 C32 109.75(12) . . ?
C31 C30 C33 109.11(12) . . ?
C33 C30 C32 110.06(12) . . ?
O4 C35 C34 112.36(11) . . ?
####################################################################### 
# 
# 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_40190
_database_code_depnum_ccdc_archive 'CCDC 1901555'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#Crystallographer: Michael R. Gau

_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'Cl, C33 H49 N4 O3'
_chemical_formula_sum            'C33 H49 Cl N4 O3'
_chemical_formula_weight         585.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'

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'
'-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                   24.8659(6)
_cell_length_b                   15.3224(4)
_cell_length_c                   20.1555(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.3740(10)
_cell_angle_gamma                90
_cell_volume                     6692.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.659
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52559
_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         27.524
_diffrn_reflns_theta_min         1.710
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                5242
_reflns_number_total             7666
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         7666
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.028
_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)+(0.0505P)²+12.5843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1499
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.31985(3) 0.33153(4) 0.79897(3) 0.03718(15) Uani 1 1 d . . . . .
O1 O 0.41701(10) 0.46678(16) 0.91121(13) 0.0692(7) Uani 1 1 d . . . . .
H1 H 0.396647 0.420803 0.892897 0.104 Uiso 1 1 calc GR . . . .
O2 O 0.10004(7) 0.69215(11) 0.72758(9) 0.0391(4) Uani 1 1 d . . . . .
H2 H 0.116824 0.730818 0.714348 0.059 Uiso 1 1 calc GR . . . .
O3 O 0.19998(8) 0.74750(10) 0.57304(9) 0.0373(4) Uani 1 1 d . . . . .
H3 H 0.194043 0.776810 0.604081 0.056 Uiso 1 1 calc GR . . . .
N1 N 0.39686(11) 0.53293(18) 0.85207(15) 0.0598(7) Uani 1 1 d D . . . .
N2 N 0.14737(8) 0.63919(12) 0.78772(10) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.17980(9) 0.65772(11) 0.57168(10) 0.0315(4) Uani 1 1 d . . . . .
N4 N 0.26287(11) 0.54373(17) 0.75452(13) 0.0548(7) Uani 1 1 d D . . . .
H4a H 0.302787 0.512757 0.770552 0.066 Uiso 0.719(13) 1 calc R . P A 1
H4b H 0.294605 0.497012 0.767672 0.066 Uiso 0.281(13) 1 calc R . P A 2
C1 C 0.2790(3) 0.6361(3) 0.7613(2) 0.0313(11) Uani 0.719(13) 1 d D . P A 1
H1a H 0.242466 0.671247 0.751875 0.038 Uiso 0.719(13) 1 calc R . P A 1
H1b H 0.289975 0.651462 0.721758 0.038 Uiso 0.719(13) 1 calc R . P A 1
C1* C 0.3036(7) 0.6167(10) 0.7574(6) 0.046(3) Uani 0.281(13) 1 d D . P A 2
H1*a H 0.279348 0.660471 0.717748 0.055 Uiso 0.281(13) 1 calc R . P A 2
H1*b H 0.336700 0.594273 0.748218 0.055 Uiso 0.281(13) 1 calc R . P A 2
C2 C 0.33246(12) 0.65961(18) 0.83903(14) 0.0450(7) Uani 1 1 d D . . . .
C3 C 0.32248(12) 0.73677(19) 0.86777(14) 0.0454(6) Uani 1 1 d . . . . .
H3a H 0.286316 0.770001 0.837437 0.054 Uiso 1 1 calc R . . . .
C4 C 0.36445(13) 0.7657(2) 0.93977(16) 0.0564(8) Uani 1 1 d . . . . .
H4 H 0.357668 0.819135 0.958383 0.068 Uiso 1 1 calc R . . . .
C5 C 0.41617(14) 0.7166(2) 0.98446(18) 0.0697(10) Uani 1 1 d . . . . .
H5 H 0.444753 0.736256 1.034222 0.084 Uiso 1 1 calc R . . . .
C6 C 0.42716(12) 0.6389(2) 0.95788(18) 0.0662(10) Uani 1 1 d . . . . .
H6 H 0.462303 0.604604 0.989820 0.079 Uiso 1 1 calc R . . . .
C7 C 0.38615(12) 0.6114(2) 0.88371(16) 0.0507(7) Uani 1 1 d . . . . .
C8 C 0.4422(3) 0.5473(6) 0.8217(5) 0.060(2) Uani 0.719(13) 1 d D U P A 1
C8* C 0.4560(8) 0.5212(13) 0.8492(10) 0.051(4) Uani 0.281(13) 1 d D U P A 2
C9 C 0.5059(3) 0.5757(7) 0.8849(5) 0.083(3) Uani 0.719(13) 1 d . U P A 1
H9a H 0.504119 0.636541 0.898572 0.125 Uiso 0.719(13) 1 calc GR . P A 1
H9b H 0.535901 0.570235 0.866854 0.125 Uiso 0.719(13) 1 calc GR . P A 1
H9c H 0.518508 0.538397 0.929602 0.125 Uiso 0.719(13) 1 calc GR . P A 1
C9* C 0.5188(9) 0.5502(15) 0.9185(10) 0.058(4) Uani 0.281(13) 1 d . U P A 2
H9*a H 0.516080 0.611540 0.930450 0.087 Uiso 0.281(13) 1 calc GR . P A 2
H9*b H 0.551822 0.543431 0.905745 0.087 Uiso 0.281(13) 1 calc GR . P A 2
H9*c H 0.527721 0.513911 0.962779 0.087 Uiso 0.281(13) 1 calc GR . P A 2
C10 C 0.4464(3) 0.4577(5) 0.7918(5) 0.070(2) Uani 0.719(13) 1 d . U P A 1
H10a H 0.468517 0.417606 0.834617 0.106 Uiso 0.719(13) 1 calc GR . P A 1
H10b H 0.468670 0.462610 0.763060 0.106 Uiso 0.719(13) 1 calc GR . P A 1
H10c H 0.404748 0.435333 0.758311 0.106 Uiso 0.719(13) 1 calc GR . P A 1
C10* C 0.4661(11) 0.4279(11) 0.8245(9) 0.060(4) Uani 0.281(13) 1 d . U P A 2
H10d H 0.479234 0.387422 0.867384 0.089 Uiso 0.281(13) 1 calc GR . P A 2
H10e H 0.497913 0.430984 0.809375 0.089 Uiso 0.281(13) 1 calc GR . P A 2
H10f H 0.427336 0.407237 0.781533 0.089 Uiso 0.281(13) 1 calc GR . P A 2
C11 C 0.4162(3) 0.6140(5) 0.7572(5) 0.0637(19) Uani 0.719(13) 1 d . U P A 1
H11a H 0.377393 0.592096 0.715181 0.096 Uiso 0.719(13) 1 calc GR . P A 1
H11b H 0.445949 0.623432 0.739217 0.096 Uiso 0.719(13) 1 calc GR . P A 1
H11c H 0.408707 0.669238 0.775745 0.096 Uiso 0.719(13) 1 calc GR . P A 1
C11* C 0.4411(9) 0.5849(12) 0.7848(10) 0.057(4) Uani 0.281(13) 1 d D U P A 2
H11d H 0.401734 0.568661 0.740425 0.086 Uiso 0.281(13) 1 calc GR . P A 2
H11e H 0.473894 0.583129 0.771253 0.086 Uiso 0.281(13) 1 calc GR . P A 2
H11f H 0.437949 0.644014 0.801160 0.086 Uiso 0.281(13) 1 calc GR . P A 2
C12 C 0.24447(10) 0.51619(16) 0.81233(13) 0.0365(5) Uani 1 1 d . . . . .
H12a H 0.252798 0.565126 0.848164 0.044 Uiso 1 1 calc R . . . .
H12b H 0.270887 0.466627 0.841958 0.044 Uiso 1 1 calc R . . . .
C13 C 0.17784(10) 0.48950(15) 0.77935(12) 0.0307(5) Uani 1 1 d . . . . .
C14 C 0.16251(12) 0.40181(17) 0.76132(15) 0.0417(6) Uani 1 1 d . . . . .
H14 H 0.194387 0.360131 0.774012 0.050 Uiso 1 1 calc R . . . .
C15 C 0.10169(12) 0.37460(18) 0.72529(16) 0.0495(7) Uani 1 1 d . . . . .
H15 H 0.091862 0.314708 0.713287 0.059 Uiso 1 1 calc R . . . .
C16 C 0.05539(12) 0.43506(19) 0.70691(16) 0.0493(7) Uani 1 1 d . . . . .
H16 H 0.013468 0.416906 0.681173 0.059 Uiso 1 1 calc R . . . .
C17 C 0.06973(11) 0.52204(17) 0.72578(13) 0.0382(6) Uani 1 1 d . . . . .
H17 H 0.037498 0.563272 0.712461 0.046 Uiso 1 1 calc R . . . .
C18 C 0.13083(10) 0.54970(15) 0.76404(12) 0.0293(5) Uani 1 1 d . . . . .
C19 C 0.14668(10) 0.66184(14) 0.86044(12) 0.0293(5) Uani 1 1 d . . . . .
C20 C 0.19692(10) 0.60872(15) 0.92530(12) 0.0330(5) Uani 1 1 d . . . . .
H20a H 0.189137 0.546357 0.913771 0.050 Uiso 1 1 calc GR . . . .
H20b H 0.196623 0.621642 0.972743 0.050 Uiso 1 1 calc GR . . . .
H20c H 0.237245 0.624056 0.931042 0.050 Uiso 1 1 calc GR . . . .
C21 C 0.08417(10) 0.64412(16) 0.85577(13) 0.0362(5) Uani 1 1 d . . . . .
H21a H 0.051536 0.674505 0.811533 0.054 Uiso 1 1 calc GR . . . .
H21b H 0.085136 0.665303 0.902225 0.054 Uiso 1 1 calc GR . . . .
H21c H 0.075908 0.581237 0.850580 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.16296(11) 0.75849(15) 0.87576(14) 0.0384(5) Uani 1 1 d . . . . .
H22a H 0.201971 0.769584 0.876273 0.058 Uiso 1 1 calc GR . . . .
H22b H 0.167218 0.774428 0.925205 0.058 Uiso 1 1 calc GR . . . .
H22c H 0.130129 0.793500 0.835648 0.058 Uiso 1 1 calc GR . . . .
C23 C 0.22110(10) 0.51220(15) 0.67436(12) 0.0316(5) Uani 1 1 d . . . . .
H23a H 0.180352 0.540766 0.654356 0.038 Uiso 1 1 calc R . . . .
H23b H 0.214867 0.448517 0.675506 0.038 Uiso 1 1 calc R . . . .
C24 C 0.24612(10) 0.53058(14) 0.62091(12) 0.0319(5) Uani 1 1 d . . . . .
C25 C 0.29088(11) 0.47463(16) 0.62210(13) 0.0385(6) Uani 1 1 d . . . . .
H25 H 0.302500 0.424125 0.653448 0.046 Uiso 1 1 calc R . . . .
C26 C 0.31852(12) 0.49147(17) 0.57852(14) 0.0440(6) Uani 1 1 d . . . . .
H26 H 0.348543 0.452443 0.579396 0.053 Uiso 1 1 calc R . . . .
C27 C 0.30222(12) 0.56568(18) 0.53345(15) 0.0447(6) Uani 1 1 d . . . . .
H27 H 0.322330 0.578738 0.504930 0.054 Uiso 1 1 calc R . . . .
C28 C 0.25667(12) 0.62097(16) 0.52980(13) 0.0390(6) Uani 1 1 d . . . . .
H28 H 0.245317 0.671288 0.498252 0.047 Uiso 1 1 calc R . . . .
C29 C 0.22730(10) 0.60288(14) 0.57250(12) 0.0317(5) Uani 1 1 d . . . . .
C30 C 0.11664(11) 0.64819(16) 0.50300(13) 0.0382(6) Uani 1 1 d . . . . .
C31 C 0.07383(12) 0.70575(18) 0.51737(16) 0.0509(7) Uani 1 1 d . . . . .
H31a H 0.076366 0.689345 0.565825 0.076 Uiso 1 1 calc GR . . . .
H31b H 0.031356 0.698187 0.475997 0.076 Uiso 1 1 calc GR . . . .
H31c H 0.086098 0.766928 0.519596 0.076 Uiso 1 1 calc GR . . . .
C32 C 0.09686(12) 0.55281(16) 0.49925(14) 0.0424(6) Uani 1 1 d . . . . .
H32a H 0.126579 0.514781 0.494698 0.064 Uiso 1 1 calc GR . . . .
H32b H 0.055847 0.544558 0.454928 0.064 Uiso 1 1 calc GR . . . .
H32c H 0.095515 0.538067 0.545725 0.064 Uiso 1 1 calc GR . . . .
C33 C 0.11500(14) 0.6738(2) 0.42836(14) 0.0563(8) Uani 1 1 d . . . . .
H33a H 0.134550 0.730969 0.434410 0.084 Uiso 1 1 calc GR . . . .
H33b H 0.072049 0.676688 0.387289 0.084 Uiso 1 1 calc GR . . . .
H33c H 0.137341 0.630090 0.415754 0.084 Uiso 1 1 calc GR . . . .


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 N1 1.454(4) . ?
O2 N2 1.454(2) . ?
O3 N3 1.460(2) . ?
N1 C7 1.445(3) . ?
N1 C8 1.540(7) . ?
N1 C8* 1.510(15) . ?
N2 C18 1.444(3) . ?
N2 C19 1.514(3) . ?
N3 C29 1.443(3) . ?
N3 C30 1.507(3) . ?
N4 C1 1.459(4) . ?
N4 C1* 1.490(10) . ?
N4 C12 1.506(3) . ?
N4 C23 1.509(3) . ?
C1 C2 1.519(5) . ?
C1* C2 1.580(11) . ?
C2 C3 1.391(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.399(4) . ?
C8 C9 1.529(8) . ?
C8 C10 1.524(8) . ?
C8 C11 1.526(9) . ?
C8* C9* 1.56(2) . ?
C8* C10* 1.57(2) . ?
C8* C11* 1.517(14) . ?
C12 C13 1.508(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.382(4) . ?
C15 C16 1.379(4) . ?
C16 C17 1.384(4) . ?
C17 C18 1.390(3) . ?
C19 C20 1.526(3) . ?
C19 C21 1.535(3) . ?
C19 C22 1.526(3) . ?
C23 C24 1.511(3) . ?
C24 C25 1.396(3) . ?
C24 C29 1.397(3) . ?
C25 C26 1.379(4) . ?
C26 C27 1.386(4) . ?
C27 C28 1.387(4) . ?
C28 C29 1.402(3) . ?
C30 C31 1.516(4) . ?
C30 C32 1.532(3) . ?
C30 C33 1.536(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C8 113.6(4) . . ?
O1 N1 C8* 89.9(6) . . ?
C7 N1 O1 106.4(2) . . ?
C7 N1 C8 112.7(4) . . ?
C7 N1 C8* 120.6(9) . . ?
O2 N2 C19 106.87(16) . . ?
C18 N2 O2 105.77(15) . . ?
C18 N2 C19 113.64(17) . . ?
O3 N3 C30 107.59(16) . . ?
C29 N3 O3 106.05(16) . . ?
C29 N3 C30 115.62(17) . . ?
C1 N4 C12 111.9(3) . . ?
C1 N4 C23 115.1(2) . . ?
C1* N4 C12 129.7(5) . . ?
C1* N4 C23 112.3(4) . . ?
C12 N4 C23 115.34(18) . . ?
N4 C1 C2 112.8(3) . . ?
N4 C1* C2 107.8(7) . . ?
C3 C2 C1 112.7(3) . . ?
C3 C2 C1* 134.8(7) . . ?
C3 C2 C7 119.3(2) . . ?
C7 C2 C1 127.9(3) . . ?
C7 C2 C1* 104.6(7) . . ?
C4 C3 C2 120.9(3) . . ?
C5 C4 C3 119.7(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C7 119.6(3) . . ?
C2 C7 N1 118.6(2) . . ?
C6 C7 N1 121.8(3) . . ?
C6 C7 C2 119.6(3) . . ?
C9 C8 N1 111.8(6) . . ?
C10 C8 N1 103.5(5) . . ?
C10 C8 C9 110.0(6) . . ?
C10 C8 C11 110.3(5) . . ?
C11 C8 N1 110.4(5) . . ?
C11 C8 C9 110.6(6) . . ?
N1 C8* C9* 119.7(15) . . ?
N1 C8* C10* 115.4(14) . . ?
N1 C8* C11* 97.0(11) . . ?
C9* C8* C10* 107.2(14) . . ?
C11* C8* C9* 107.4(14) . . ?
C11* C8* C10* 108.9(14) . . ?
N4 C12 C13 114.84(19) . . ?
C14 C13 C12 118.5(2) . . ?
C14 C13 C18 119.0(2) . . ?
C18 C13 C12 122.5(2) . . ?
C15 C14 C13 121.1(2) . . ?
C16 C15 C14 119.5(2) . . ?
C15 C16 C17 120.3(2) . . ?
C16 C17 C18 120.7(2) . . ?
C13 C18 N2 118.78(19) . . ?
C17 C18 N2 122.0(2) . . ?
C17 C18 C13 119.3(2) . . ?
N2 C19 C20 108.29(17) . . ?
N2 C19 C21 113.08(17) . . ?
N2 C19 C22 106.89(18) . . ?
C20 C19 C21 109.69(18) . . ?
C22 C19 C20 108.64(18) . . ?
C22 C19 C21 110.12(19) . . ?
N4 C23 C24 113.31(18) . . ?
C25 C24 C23 118.5(2) . . ?
C25 C24 C29 119.4(2) . . ?
C29 C24 C23 122.1(2) . . ?
C26 C25 C24 121.1(2) . . ?
C25 C26 C27 119.6(2) . . ?
C26 C27 C28 120.3(2) . . ?
C27 C28 C29 120.3(2) . . ?
C24 C29 N3 117.5(2) . . ?
C24 C29 C28 119.3(2) . . ?
C28 C29 N3 123.2(2) . . ?
N3 C30 C31 106.33(19) . . ?
N3 C30 C32 107.60(19) . . ?
N3 C30 C33 113.0(2) . . ?
C31 C30 C32 109.0(2) . . ?
C31 C30 C33 110.8(2) . . ?
C32 C30 C33 110.0(2) . . ?
####################################################################### 
# 
# 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_40181
_database_code_depnum_ccdc_archive 'CCDC 1901557'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

# Crystallographer: Thibault Cheisson

_audit_creation_date             2017-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C33 H49 N4 O3, 0.5(C6 H6), Br'
_chemical_formula_sum            'C36 H52 Br N4 O3'
_chemical_formula_weight         668.72

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'

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'
'-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                   29.0180(11)
_cell_length_b                   15.6456(6)
_cell_length_c                   19.7456(7)
_cell_angle_alpha                90
_cell_angle_beta                 129.4510(10)
_cell_angle_gamma                90
_cell_volume                     6922.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.504
_cell_measurement_theta_min      2.418
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30306
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.587
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                6610
_reflns_number_total             7927
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
Bruker APEX2 v2014.11-0
;
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
shelXL v2014/7
;
_computing_structure_solution    
;
'shelXS-97'
;
_refine_diff_density_max         1.571
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         7927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.035
_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)+(0.0595P)²+12.8587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1144
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct

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 0.40576(9) 0.21684(13) 0.45779(13) 0.0397(5) Uani 1 1 d . . . . .
H1 H 0.3899 0.2567 0.4209 0.060 Uiso 1 1 calc GR . . . .
O2 O 0.32067(9) 0.24682(11) 0.15653(11) 0.0344(4) Uani 1 1 d . . . . .
H2 H 0.3226 0.2785 0.1926 0.052 Uiso 1 1 calc GR . . . .
O3 O 0.08244(7) 0.04041(10) 0.12955(10) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.0983 -0.0081 0.1471 0.034 Uiso 1 1 calc GR . . . .
N1 N 0.35971(10) 0.16879(14) 0.45033(13) 0.0297(5) Uani 1 1 d . . . . .
N2 N 0.33396(8) 0.15939(12) 0.18823(12) 0.0195(4) Uani 1 1 d . . . . .
N3 N 0.11691(8) 0.09364(12) 0.11587(11) 0.0183(4) Uani 1 1 d . . . . .
N4 N 0.24249(9) 0.07183(13) 0.23798(12) 0.0231(4) Uani 1 1 d . . . . .
H4 H 0.2016 0.0478 0.1929 0.028 Uiso 1 1 calc R . . . .
C1 C 0.25977(10) 0.05117(17) 0.32718(14) 0.0261(5) Uani 1 1 d . . . . .
H1a H 0.2525 0.1022 0.3490 0.031 Uiso 1 1 calc R . . . .
H1b H 0.2338 0.0046 0.3199 0.031 Uiso 1 1 calc R . . . .
C2 C 0.32446(10) 0.02434(17) 0.39491(14) 0.0258(5) Uani 1 1 d . . . . .
C3 C 0.33673(12) -0.06324(18) 0.40102(16) 0.0314(6) Uani 1 1 d . . . . .
H3a H 0.3045 -0.1026 0.3688 0.038 Uiso 1 1 calc R . . . .
C4 C 0.39440(12) -0.09367(18) 0.45268(18) 0.0352(6) Uani 1 1 d . . . . .
H4a H 0.4018 -0.1532 0.4549 0.042 Uiso 1 1 calc R . . . .
C5 C 0.44128(12) -0.03669(19) 0.50113(16) 0.0341(6) Uani 1 1 d . . . . .
H5 H 0.4811 -0.0571 0.5355 0.041 Uiso 1 1 calc R . . . .
C6 C 0.43095(11) 0.04890(19) 0.50019(16) 0.0318(6) Uani 1 1 d . . . . .
H6 H 0.4637 0.0872 0.5346 0.038 Uiso 1 1 calc R . . . .
C7 C 0.37225(11) 0.08045(16) 0.44863(15) 0.0265(5) Uani 1 1 d . . . . .
C8 C 0.36472(13) 0.19341(18) 0.52907(16) 0.0350(6) Uani 1 1 d . . . . .
C9 C 0.34825(16) 0.2864(2) 0.5195(2) 0.0499(8) Uani 1 1 d . . . . .
H9a H 0.3089 0.2957 0.4624 0.075 Uiso 1 1 calc GR . . . .
H9b H 0.3780 0.3212 0.5234 0.075 Uiso 1 1 calc GR . . . .
H9c H 0.3472 0.3029 0.5664 0.075 Uiso 1 1 calc GR . . . .
C10 C 0.31817(15) 0.1416(2) 0.5253(2) 0.0463(8) Uani 1 1 d . . . . .
H10a H 0.2784 0.1523 0.4693 0.069 Uiso 1 1 calc GR . . . .
H10b H 0.3189 0.1589 0.5736 0.069 Uiso 1 1 calc GR . . . .
H10c H 0.3275 0.0806 0.5304 0.069 Uiso 1 1 calc GR . . . .
C11 C 0.42676(13) 0.1802(2) 0.61704(17) 0.0457(8) Uani 1 1 d . . . . .
H11a H 0.4295 0.2103 0.6631 0.069 Uiso 1 1 calc GR . . . .
H11b H 0.4568 0.2028 0.6139 0.069 Uiso 1 1 calc GR . . . .
H11c H 0.4337 0.1190 0.6307 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.28226(10) 0.02883(15) 0.22343(15) 0.0228(5) Uani 1 1 d . . . . .
H12a H 0.2832 -0.0333 0.2339 0.027 Uiso 1 1 calc R . . . .
H12b H 0.3234 0.0509 0.2673 0.027 Uiso 1 1 calc R . . . .
C13 C 0.26306(10) 0.04192(15) 0.13267(15) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.22074(10) -0.01347(16) 0.06593(16) 0.0278(5) Uani 1 1 d . . . . .
H14 H 0.2064 -0.0601 0.0787 0.033 Uiso 1 1 calc R . . . .
C15 C 0.19949(11) -0.00093(18) -0.01881(17) 0.0326(6) Uani 1 1 d . . . . .
H15 H 0.1709 -0.0393 -0.0639 0.039 Uiso 1 1 calc R . . . .
C16 C 0.21952(11) 0.06675(19) -0.03803(15) 0.0339(6) Uani 1 1 d . . . . .
H16 H 0.2035 0.0763 -0.0969 0.041 Uiso 1 1 calc R . . . .
C17 C 0.26350(12) 0.12202(16) 0.02852(15) 0.0273(5) Uani 1 1 d . . . . .
H17 H 0.2772 0.1688 0.0149 0.033 Uiso 1 1 calc R . . . .
C18 C 0.28683(10) 0.10766(15) 0.11473(14) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.39587(11) 0.13858(16) 0.22163(16) 0.0265(5) Uani 1 1 d . . . . .
C20 C 0.40421(14) 0.1563(2) 0.1536(2) 0.0490(8) Uani 1 1 d . . . . .
H20a H 0.3925 0.2153 0.1328 0.073 Uiso 1 1 calc GR . . . .
H20b H 0.3792 0.1169 0.1041 0.073 Uiso 1 1 calc GR . . . .
H20c H 0.4462 0.1479 0.1806 0.073 Uiso 1 1 calc GR . . . .
C21 C 0.43789(12) 0.19436(19) 0.30272(17) 0.0339(6) Uani 1 1 d . . . . .
H21a H 0.4306 0.1845 0.3442 0.051 Uiso 1 1 calc GR . . . .
H21b H 0.4307 0.2547 0.2854 0.051 Uiso 1 1 calc GR . . . .
H21c H 0.4793 0.1797 0.3306 0.051 Uiso 1 1 calc GR . . . .
C22 C 0.40877(11) 0.04483(18) 0.24848(19) 0.0358(6) Uani 1 1 d . . . . .
H22a H 0.3794 0.0090 0.1977 0.054 Uiso 1 1 calc GR . . . .
H22b H 0.4062 0.0347 0.2950 0.054 Uiso 1 1 calc GR . . . .
H22c H 0.4489 0.0305 0.2700 0.054 Uiso 1 1 calc GR . . . .
C23 C 0.23731(10) 0.16679(15) 0.22185(16) 0.0259(5) Uani 1 1 d . . . . .
H23a H 0.2303 0.1779 0.1666 0.031 Uiso 1 1 calc R . . . .
H23b H 0.2754 0.1946 0.2702 0.031 Uiso 1 1 calc R . . . .
C24 C 0.18705(10) 0.20559(15) 0.21566(15) 0.0214(4) Uani 1 1 d . . . . .
C25 C 0.19973(10) 0.27929(15) 0.26413(15) 0.0240(5) Uani 1 1 d . . . . .
H25 H 0.2387 0.3031 0.2985 0.029 Uiso 1 1 calc R . . . .
C26 C 0.15665(11) 0.31843(16) 0.26319(15) 0.0266(5) Uani 1 1 d . . . . .
H26 H 0.1657 0.3696 0.2955 0.032 Uiso 1 1 calc R . . . .
C27 C 0.10039(11) 0.28306(17) 0.21517(16) 0.0284(5) Uani 1 1 d . . . . .
H27 H 0.0709 0.3096 0.2150 0.034 Uiso 1 1 calc R . . . .
C28 C 0.08662(10) 0.20886(16) 0.16706(15) 0.0235(5) Uani 1 1 d . . . . .
H28 H 0.0482 0.1839 0.1355 0.028 Uiso 1 1 calc R . . . .
C29 C 0.12940(9) 0.17108(14) 0.16521(13) 0.0186(4) Uani 1 1 d . . . . .
C30 C 0.07923(10) 0.10592(16) 0.01731(14) 0.0230(5) Uani 1 1 d . . . . .
C31 C 0.11614(12) 0.16002(17) 0.00248(16) 0.0287(5) Uani 1 1 d . . . . .
H31a H 0.1534 0.1301 0.0265 0.043 Uiso 1 1 calc GR . . . .
H31b H 0.1253 0.2153 0.0320 0.043 Uiso 1 1 calc GR . . . .
H31c H 0.0933 0.1693 -0.0605 0.043 Uiso 1 1 calc GR . . . .
C32 C 0.01926(11) 0.14879(17) -0.02519(16) 0.0302(5) Uani 1 1 d . . . . .
H32a H 0.0258 0.2087 -0.0066 0.045 Uiso 1 1 calc GR . . . .
H32b H -0.0011 0.1191 -0.0072 0.045 Uiso 1 1 calc GR . . . .
H32c H -0.0054 0.1461 -0.0891 0.045 Uiso 1 1 calc GR . . . .
C33 C 0.06925(11) 0.01673(16) -0.02173(15) 0.0265(5) Uani 1 1 d . . . . .
H33a H 0.0381 -0.0127 -0.0250 0.040 Uiso 1 1 calc GR . . . .
H33b H 0.1064 -0.0161 0.0156 0.040 Uiso 1 1 calc GR . . . .
H33c H 0.0569 0.0219 -0.0807 0.040 Uiso 1 1 calc GR . . . .
C34 C 0.5000 0.3986(3) 0.2500 0.0301(8) Uani 1 2 d S T P . .
H34 H 0.5000 0.3378 0.2500 0.036 Uiso 1 2 calc RS T P . .
C35 C 0.45470(11) 0.44233(19) 0.24025(15) 0.0325(6) Uani 1 1 d . . . . .
H35 H 0.4236 0.4119 0.2332 0.039 Uiso 1 1 calc R . . . .
C36 C 0.45502(12) 0.5307(2) 0.24080(16) 0.0375(7) Uani 1 1 d . . . . .
H36 H 0.4243 0.5611 0.2349 0.045 Uiso 1 1 calc R . . . .
C37 C 0.5000 0.5747(3) 0.2500 0.0399(10) Uani 1 2 d S T P . .
H37 H 0.5000 0.6354 0.2500 0.048 Uiso 1 2 calc RS T P . .
Br1 Br 0.33434(2) 0.36914(2) 0.30424(2) 0.02294(8) Uani 1 1 d . . . . .


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 N1 1.457(3) . ?
O2 N2 1.451(2) . ?
O3 N3 1.453(2) . ?
N1 C7 1.435(3) . ?
N1 C8 1.516(3) . ?
N2 C18 1.452(3) . ?
N2 C19 1.504(3) . ?
N3 C29 1.449(3) . ?
N3 C30 1.522(3) . ?
N4 C1 1.528(3) . ?
N4 C12 1.513(3) . ?
N4 C23 1.507(3) . ?
C1 C2 1.516(3) . ?
C2 C3 1.402(4) . ?
C2 C7 1.396(3) . ?
C3 C4 1.378(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.370(4) . ?
C6 C7 1.406(3) . ?
C8 C9 1.506(4) . ?
C8 C10 1.536(4) . ?
C8 C11 1.525(4) . ?
C12 C13 1.515(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.404(3) . ?
C14 C15 1.381(4) . ?
C15 C16 1.372(4) . ?
C16 C17 1.404(4) . ?
C17 C18 1.394(3) . ?
C19 C20 1.533(3) . ?
C19 C21 1.527(3) . ?
C19 C22 1.523(4) . ?
C23 C24 1.511(3) . ?
C24 C25 1.390(3) . ?
C24 C29 1.401(3) . ?
C25 C26 1.382(3) . ?
C26 C27 1.380(4) . ?
C27 C28 1.388(3) . ?
C28 C29 1.396(3) . ?
C30 C31 1.532(3) . ?
C30 C32 1.525(3) . ?
C30 C33 1.530(3) . ?
C34 C35 1.383(3) . ?
C34 C35 1.383(3) 2_655 ?
C35 C36 1.382(4) . ?
C36 C37 1.382(4) . ?
C37 C36 1.382(4) 2_655 ?

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
O1 N1 C8 106.32(19) . . ?
C7 N1 O1 105.63(19) . . ?
C7 N1 C8 114.1(2) . . ?
O2 N2 C18 105.72(17) . . ?
O2 N2 C19 108.01(17) . . ?
C18 N2 C19 114.93(17) . . ?
O3 N3 C30 106.86(15) . . ?
C29 N3 O3 105.18(15) . . ?
C29 N3 C30 115.07(17) . . ?
C12 N4 C1 113.18(17) . . ?
C23 N4 C1 111.57(18) . . ?
C23 N4 C12 112.58(18) . . ?
C2 C1 N4 113.01(19) . . ?
C3 C2 C1 116.8(2) . . ?
C7 C2 C1 124.8(2) . . ?
C7 C2 C3 118.3(2) . . ?
C4 C3 C2 121.6(3) . . ?
C3 C4 C5 119.2(3) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 120.5(2) . . ?
C2 C7 N1 118.6(2) . . ?
C2 C7 C6 119.4(2) . . ?
C6 C7 N1 122.0(2) . . ?
N1 C8 C10 107.9(2) . . ?
N1 C8 C11 114.1(2) . . ?
C9 C8 N1 107.5(2) . . ?
C9 C8 C10 107.8(3) . . ?
C9 C8 C11 108.9(3) . . ?
C11 C8 C10 110.4(2) . . ?
N4 C12 C13 114.39(18) . . ?
C14 C13 C12 118.4(2) . . ?
C14 C13 C18 119.8(2) . . ?
C18 C13 C12 121.8(2) . . ?
C15 C14 C13 120.3(2) . . ?
C16 C15 C14 120.2(2) . . ?
C15 C16 C17 120.6(2) . . ?
C18 C17 C16 119.4(2) . . ?
C13 C18 N2 117.25(19) . . ?
C17 C18 N2 123.3(2) . . ?
C17 C18 C13 119.4(2) . . ?
N2 C19 C20 112.7(2) . . ?
N2 C19 C21 105.75(19) . . ?
N2 C19 C22 108.78(19) . . ?
C21 C19 C20 110.5(2) . . ?
C22 C19 C20 109.8(2) . . ?
C22 C19 C21 109.2(2) . . ?
N4 C23 C24 112.00(19) . . ?
C25 C24 C23 117.2(2) . . ?
C25 C24 C29 118.9(2) . . ?
C29 C24 C23 123.9(2) . . ?
C26 C25 C24 121.1(2) . . ?
C27 C26 C25 119.8(2) . . ?
C26 C27 C28 120.4(2) . . ?
C27 C28 C29 119.9(2) . . ?
C24 C29 N3 118.41(19) . . ?
C28 C29 N3 121.66(19) . . ?
C28 C29 C24 119.8(2) . . ?
N3 C30 C31 107.02(18) . . ?
N3 C30 C32 113.61(19) . . ?
N3 C30 C33 106.34(18) . . ?
C32 C30 C31 110.1(2) . . ?
C32 C30 C33 109.8(2) . . ?
C33 C30 C31 109.8(2) . . ?
C35 C34 C35 120.6(4) . 2_655 ?
C36 C35 C34 119.5(3) . . ?
C37 C36 C35 120.0(3) . . ?
C36 C37 C36 120.2(4) 2_655 . ?
####################################################################### 
# 
# 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_40270
_database_code_depnum_ccdc_archive 'CCDC 1901559'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

#Crystallographer: Michael R. Gau

_audit_creation_date             2018-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'Br, 2(C H Cl3), C33 H49 N4 O3'
_chemical_formula_sum            'C35 H51 Br Cl6 N4 O3'
_chemical_formula_weight         868.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   21.169(2)
_cell_length_b                   12.0506(11)
_cell_length_c                   16.8977(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.492(6)
_cell_angle_gamma                90
_cell_volume                     4273.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.348
_cell_measurement_theta_min      2.363
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7537
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.081
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                4884
_reflns_number_total             7537
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.810
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         7537
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.1065
_refine_ls_restrained_S_all      1.067
_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)+(0.1085P)²+23.3037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2674
_refine_ls_wR_factor_ref         0.2971
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_refine_special_details          
;
 Refined as a 2-component twin. 
 TWINROTMAT was used to determine twin matrix
 and generate an HKL5 file.
;

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 0.75574(5) 0.40973(8) 0.52160(5) 0.0542(3) Uani 1 1 d D . . . .
Cl1 Cl 0.8300(3) 0.7133(4) 0.4703(3) 0.176(3) Uani 1 1 d . . . . .
Cl2 Cl 0.91944(19) 0.5349(6) 0.4526(3) 0.144(2) Uani 1 1 d . . . . .
Cl3 Cl 0.9276(3) 0.6649(5) 0.5991(3) 0.163(2) Uani 1 1 d . . . . .
C34 C 0.8773(6) 0.6120(11) 0.5202(8) 0.083(4) Uani 1 1 d . . . . .
H34 H 0.848144 0.558701 0.542737 0.100 Uiso 1 1 calc R . . . .
Cl4 Cl 0.6524(3) 0.6040(5) 0.3682(4) 0.0781(17) Uani 0.5 1 d . . P A 1
Cl4* Cl 0.6672(8) 0.6801(13) 0.4394(14) 0.257(11) Uani 0.5 1 d . . P A 2
Cl5 Cl 0.6190(5) 0.7345(6) 0.4945(5) 0.114(3) Uani 0.5 1 d . . P A 1
Cl5* Cl 0.5591(4) 0.6769(8) 0.5078(6) 0.123(3) Uani 0.5 1 d . . P A 2
Cl6 Cl 0.5631(4) 0.5138(11) 0.4615(7) 0.147(5) Uani 0.5 1 d . . P A 1
Cl6* Cl 0.5848(7) 0.4980(14) 0.4018(7) 0.206(9) Uani 0.5 1 d . . P A 2
C35 C 0.6210(7) 0.5946(12) 0.4705(8) 0.102(5) Uani 1 1 d . . . . .
H35 H 0.655331 0.559634 0.508665 0.122 Uiso 0.5 1 calc R . P A 1
H35a H 0.644784 0.553214 0.516285 0.122 Uiso 0.5 1 calc R . P A 2
O1 O 0.8224(3) 0.2918(7) 0.6856(5) 0.073(2) Uani 1 1 d . . . . .
H1 H 0.803221 0.322024 0.644560 0.110 Uiso 1 1 calc GR . . . .
O2 O 0.7024(9) 0.1689(10) 0.5492(6) 0.171(6) Uani 1 1 d . . . . .
H2 H 0.708569 0.237775 0.549651 0.256 Uiso 1 1 calc DGR . . . .
O3 O 0.6575(7) 0.4628(13) 0.6360(8) 0.067(4) Uani 0.5 1 d . . P B 1
H3 H 0.687399 0.434948 0.614505 0.101 Uiso 0.5 1 calc DGR . P B 1
O3* O 0.7256(7) 0.4298(14) 0.7064(6) 0.085(5) Uani 0.5 1 d . . P B 2
H3* H 0.726505 0.425791 0.656956 0.128 Uiso 0.5 1 calc DGR . P B 2
N1 N 0.8785(4) 0.3511(8) 0.7114(6) 0.069(2) Uani 1 1 d . . . . .
N2 N 0.6796(8) 0.1355(11) 0.6238(6) 0.124(6) Uani 1 1 d . . . . .
N3 N 0.6758(6) 0.4713(10) 0.7192(6) 0.089(3) Uani 1 1 d . . . . .
N4 N 0.7470(3) 0.2434(6) 0.8044(4) 0.0451(17) Uani 1 1 d . . . . .
H4 H 0.747176 0.278212 0.750729 0.054 Uiso 1 1 calc R . . . .
C1 C 0.8143(4) 0.2261(8) 0.8410(6) 0.052(2) Uani 1 1 d . . . . .
H1a H 0.835932 0.176448 0.806403 0.062 Uiso 1 1 calc R . . . .
H1b H 0.814679 0.189298 0.893480 0.062 Uiso 1 1 calc R . . . .
C2 C 0.8511(5) 0.3368(9) 0.8524(6) 0.061(3) Uani 1 1 d . . . . .
C3 C 0.8548(6) 0.3895(11) 0.9281(7) 0.076(3) Uani 1 1 d . . . . .
H3a H 0.835135 0.355215 0.969190 0.092 Uiso 1 1 calc R . . . .
C4 C 0.8856(7) 0.4875(12) 0.9434(8) 0.093(4) Uani 1 1 d . . . . .
H4a H 0.888644 0.518721 0.995341 0.112 Uiso 1 1 calc R . . . .
C5 C 0.9125(7) 0.5423(14) 0.8846(9) 0.104(5) Uani 1 1 d . . . . .
H5 H 0.934199 0.610704 0.895242 0.125 Uiso 1 1 calc R . . . .
C6 C 0.9068(6) 0.4939(11) 0.8082(8) 0.086(4) Uani 1 1 d . . . . .
H6 H 0.922651 0.533432 0.766302 0.104 Uiso 1 1 calc R . . . .
C7 C 0.8789(5) 0.3906(9) 0.7916(7) 0.062(3) Uani 1 1 d . . . . .
C8 C 0.9343(4) 0.2828(9) 0.6958(6) 0.061(3) Uani 1 1 d . . . . .
C9 C 0.9385(7) 0.1732(13) 0.7378(11) 0.119(6) Uani 1 1 d . . . . .
H9a H 0.947135 0.185253 0.795551 0.178 Uiso 1 1 calc GR . . . .
H9b H 0.972929 0.129162 0.720122 0.178 Uiso 1 1 calc GR . . . .
H9c H 0.898010 0.133420 0.725236 0.178 Uiso 1 1 calc GR . . . .
C10 C 0.9270(7) 0.2629(15) 0.6052(8) 0.113(5) Uani 1 1 d . . . . .
H10a H 0.886656 0.224378 0.588423 0.169 Uiso 1 1 calc GR . . . .
H10b H 0.962466 0.217245 0.592015 0.169 Uiso 1 1 calc GR . . . .
H10c H 0.927085 0.334233 0.577417 0.169 Uiso 1 1 calc GR . . . .
C11 C 0.9958(5) 0.3455(13) 0.7186(9) 0.095(4) Uani 1 1 d . . . . .
H11a H 0.994570 0.415358 0.688679 0.142 Uiso 1 1 calc GR . . . .
H11b H 1.031685 0.300408 0.705883 0.142 Uiso 1 1 calc GR . . . .
H11c H 1.001101 0.361465 0.775923 0.142 Uiso 1 1 calc GR . . . .
C12 C 0.7127(6) 0.1319(9) 0.7936(6) 0.069(3) Uani 1 1 d . . . . .
H12a H 0.667919 0.144375 0.770350 0.083 Uiso 1 1 calc R . . . .
H12b H 0.712614 0.096389 0.846401 0.083 Uiso 1 1 calc R . . . .
C13 C 0.7450(6) 0.0536(10) 0.7387(8) 0.079(4) Uani 1 1 d . . . . .
C14 C 0.7888(8) -0.0247(11) 0.7777(10) 0.095(4) Uani 1 1 d . . . . .
H14 H 0.792995 -0.029125 0.834247 0.115 Uiso 1 1 calc R . . . .
C15 C 0.8264(9) -0.0965(13) 0.7367(13) 0.113(5) Uani 1 1 d . . . . .
H15 H 0.858663 -0.144144 0.762023 0.135 Uiso 1 1 calc R . . . .
C16 C 0.8099(11) -0.0878(15) 0.6545(16) 0.130(7) Uani 1 1 d . . . . .
H16 H 0.831831 -0.135928 0.622927 0.156 Uiso 1 1 calc R . . . .
C17 C 0.7654(11) -0.0178(15) 0.6129(10) 0.124(7) Uani 1 1 d . . . . .
H17 H 0.759304 -0.016890 0.556229 0.149 Uiso 1 1 calc R . . . .
C18 C 0.7286(7) 0.0535(13) 0.6578(8) 0.096(5) Uani 1 1 d . . . . .
C19 C 0.6205(10) 0.0791(14) 0.5976(9) 0.125(7) Uani 1 1 d . . . . .
C20 C 0.5739(11) 0.180(2) 0.5685(13) 0.189(11) Uani 1 1 d . . . . .
H20a H 0.531109 0.151664 0.550471 0.284 Uiso 1 1 calc GR . . . .
H20b H 0.590130 0.219251 0.524444 0.284 Uiso 1 1 calc DGR . . . .
H20c H 0.571939 0.231939 0.612999 0.284 Uiso 1 1 calc GR . . . .
C21 C 0.6153(12) -0.0018(18) 0.5337(13) 0.197(12) Uani 1 1 d . . . . .
H21a H 0.651212 0.006886 0.503028 0.296 Uiso 1 1 calc GR . . . .
H21b H 0.575240 0.009717 0.498439 0.296 Uiso 1 1 calc GR . . . .
H21c H 0.615861 -0.076710 0.556307 0.296 Uiso 1 1 calc GR . . . .
C22 C 0.5958(10) 0.027(2) 0.6691(12) 0.195(12) Uani 1 1 d . . . . .
H22a H 0.588738 0.084663 0.707791 0.292 Uiso 1 1 calc GR . . . .
H22b H 0.627061 -0.026708 0.694161 0.292 Uiso 1 1 calc GR . . . .
H22c H 0.555476 -0.011450 0.651717 0.292 Uiso 1 1 calc GR . . . .
C23 C 0.7129(5) 0.3190(9) 0.8546(6) 0.063(3) Uani 1 1 d . . . . .
H23a H 0.735339 0.391234 0.860320 0.075 Uiso 1 1 calc R . . . .
H23b H 0.713606 0.286537 0.908506 0.075 Uiso 1 1 calc R . . . .
C24 C 0.6431(6) 0.3382(12) 0.8177(7) 0.081(4) Uani 1 1 d . . . . .
C25 C 0.5947(6) 0.273(2) 0.8465(10) 0.141(8) Uani 1 1 d . . . . .
H25 H 0.605182 0.220608 0.887855 0.169 Uiso 1 1 calc R . . . .
C26 C 0.5312(7) 0.289(2) 0.8127(12) 0.164(10) Uani 1 1 d . . . . .
H26 H 0.498353 0.248672 0.833420 0.197 Uiso 1 1 calc R . . . .
C27 C 0.5165(6) 0.357(3) 0.7532(11) 0.219(16) Uani 1 1 d . . . . .
H27 H 0.473087 0.363804 0.731108 0.262 Uiso 1 1 calc R . . . .
C28 C 0.5619(7) 0.4206(19) 0.7208(9) 0.140(8) Uani 1 1 d . . . . .
H28 H 0.549164 0.469526 0.677542 0.168 Uiso 1 1 calc R . . . .
C29 C 0.6278(5) 0.4118(12) 0.7529(7) 0.079(4) Uani 1 1 d . . . . .
C30 C 0.6860(9) 0.5884(12) 0.7450(8) 0.102(5) Uani 1 1 d . . . . .
C31 C 0.7156(9) 0.5924(12) 0.8317(9) 0.126(7) Uani 1 1 d . . . . .
H31a H 0.685402 0.562484 0.865536 0.189 Uiso 1 1 calc GR . . . .
H31b H 0.725833 0.669378 0.846913 0.189 Uiso 1 1 calc GR . . . .
H31c H 0.754629 0.547783 0.838553 0.189 Uiso 1 1 calc GR . . . .
C32 C 0.7372(14) 0.634(2) 0.6944(13) 0.220(15) Uani 1 1 d . . . . .
H32a H 0.777326 0.593259 0.708670 0.329 Uiso 1 1 calc DGR . . . .
H32b H 0.744135 0.712785 0.705273 0.329 Uiso 1 1 calc GR . . . .
H32c H 0.722376 0.622819 0.637511 0.329 Uiso 1 1 calc DGR . . . .
C33 C 0.6269(15) 0.659(2) 0.7330(16) 0.26(2) Uani 1 1 d . . . . .
H33a H 0.638759 0.737361 0.739688 0.392 Uiso 1 1 calc GR . . . .
H33b H 0.598814 0.638553 0.772438 0.392 Uiso 1 1 calc GR . . . .
H33c H 0.604579 0.647072 0.679140 0.392 Uiso 1 1 calc GR . . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C34 1.727(13) . ?
Cl2 C34 1.797(15) . ?
Cl3 C34 1.719(12) . ?
Cl4 C35 1.934(18) . ?
Cl4* C35 1.56(2) . ?
Cl5 C35 1.737(16) . ?
Cl5* C35 1.821(16) . ?
Cl6 C35 1.557(18) . ?
Cl6* C35 1.748(18) . ?
O1 N1 1.405(10) . ?
O2 N2 1.463(16) . ?
O3 N3 1.413(15) . ?
O3* N3 1.211(15) . ?
N1 C7 1.435(14) . ?
N1 C8 1.492(13) . ?
N2 C18 1.49(2) . ?
N2 C19 1.441(19) . ?
N3 C29 1.422(16) . ?
N3 C30 1.484(17) . ?
N4 C1 1.492(11) . ?
N4 C12 1.526(12) . ?
N4 C23 1.493(12) . ?
C1 C2 1.545(14) . ?
C2 C3 1.421(15) . ?
C2 C7 1.407(14) . ?
C3 C4 1.357(16) . ?
C4 C5 1.376(19) . ?
C5 C6 1.407(19) . ?
C6 C7 1.391(15) . ?
C8 C9 1.497(18) . ?
C8 C10 1.537(17) . ?
C8 C11 1.511(16) . ?
C12 C13 1.543(18) . ?
C13 C14 1.423(19) . ?
C13 C18 1.366(18) . ?
C14 C15 1.42(2) . ?
C15 C16 1.39(3) . ?
C16 C17 1.39(3) . ?
C17 C18 1.44(2) . ?
C19 C20 1.60(3) . ?
C19 C21 1.45(2) . ?
C19 C22 1.52(2) . ?
C23 C24 1.543(15) . ?
C24 C25 1.42(2) . ?
C24 C29 1.414(17) . ?
C25 C26 1.40(2) . ?
C26 C27 1.30(3) . ?
C27 C28 1.40(3) . ?
C28 C29 1.434(17) . ?
C30 C31 1.517(18) . ?
C30 C32 1.56(3) . ?
C30 C33 1.50(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C34 Cl2 111.1(8) . . ?
Cl3 C34 Cl1 112.2(8) . . ?
Cl3 C34 Cl2 112.1(7) . . ?
Cl4* C35 Cl5* 105.6(10) . . ?
Cl4* C35 Cl6* 117.2(15) . . ?
Cl5 C35 Cl4 100.0(9) . . ?
Cl6 C35 Cl4 107.9(9) . . ?
Cl6 C35 Cl5 125.9(12) . . ?
Cl6* C35 Cl5* 108.6(9) . . ?
O1 N1 C7 111.3(8) . . ?
O1 N1 C8 108.7(8) . . ?
C7 N1 C8 116.2(8) . . ?
O2 N2 C18 102.9(15) . . ?
C19 N2 O2 103.7(11) . . ?
C19 N2 C18 109.7(12) . . ?
O3 N3 C29 104.1(11) . . ?
O3 N3 C30 111.9(11) . . ?
O3* N3 C29 123.1(13) . . ?
O3* N3 C30 110.4(14) . . ?
C29 N3 C30 116.4(12) . . ?
C1 N4 C12 109.8(8) . . ?
C1 N4 C23 110.9(7) . . ?
C23 N4 C12 110.4(8) . . ?
N4 C1 C2 111.7(8) . . ?
C3 C2 C1 117.8(9) . . ?
C7 C2 C1 124.0(9) . . ?
C7 C2 C3 118.2(10) . . ?
C4 C3 C2 121.9(12) . . ?
C3 C4 C5 120.9(13) . . ?
C4 C5 C6 118.0(12) . . ?
C7 C6 C5 122.6(12) . . ?
C2 C7 N1 125.8(9) . . ?
C6 C7 N1 116.0(10) . . ?
C6 C7 C2 118.2(11) . . ?
N1 C8 C9 113.7(10) . . ?
N1 C8 C10 106.4(9) . . ?
N1 C8 C11 110.8(10) . . ?
C9 C8 C10 109.0(13) . . ?
C9 C8 C11 109.0(10) . . ?
C11 C8 C10 107.7(11) . . ?
N4 C12 C13 111.7(9) . . ?
C14 C13 C12 116.1(11) . . ?
C18 C13 C12 121.8(13) . . ?
C18 C13 C14 121.8(14) . . ?
C15 C14 C13 123.6(15) . . ?
C16 C15 C14 110.9(18) . . ?
C17 C16 C15 128.2(18) . . ?
C16 C17 C18 118.3(16) . . ?
C13 C18 N2 117.3(14) . . ?
C13 C18 C17 116.3(17) . . ?
C17 C18 N2 126.0(14) . . ?
N2 C19 C20 102.1(13) . . ?
N2 C19 C21 122(2) . . ?
N2 C19 C22 109.1(11) . . ?
C21 C19 C20 107.4(15) . . ?
C21 C19 C22 108.3(16) . . ?
C22 C19 C20 107(2) . . ?
N4 C23 C24 111.7(8) . . ?
C25 C24 C23 118.3(12) . . ?
C29 C24 C23 121.1(11) . . ?
C29 C24 C25 120.4(12) . . ?
C26 C25 C24 118.9(18) . . ?
C27 C26 C25 121.1(18) . . ?
C26 C27 C28 122.8(14) . . ?
C27 C28 C29 119.8(17) . . ?
N3 C29 C28 121.5(14) . . ?
C24 C29 N3 121.6(10) . . ?
C24 C29 C28 116.9(14) . . ?
N3 C30 C31 109.9(11) . . ?
N3 C30 C32 104.7(14) . . ?
N3 C30 C33 114.4(17) . . ?
C31 C30 C32 106.7(16) . . ?
C33 C30 C31 110.1(15) . . ?
C33 C30 C32 110.7(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.694(3)
2 0.306(3)
#===END
####################################################################### 
# 
# 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_40169
_database_code_depnum_ccdc_archive 'CCDC 1901556'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

# Crystallographer: Michael Gau

_audit_creation_date             2017-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'Br, C33 H49 N4 O3, C2 H6 O'
_chemical_formula_sum            'C35 H55 Br N4 O4'
_chemical_formula_weight         675.74

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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                   16.9397(8)
_cell_length_b                   19.8774(9)
_cell_length_c                   21.6754(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7298.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.384
_cell_measurement_theta_min      2.455
_exptl_absorpt_coefficient_mu    1.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            45991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         1.838
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                5481
_reflns_number_total             8374
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         8374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+2.8877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0887
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.19546(2) 0.82956(2) 0.74190(2) 0.02083(7) Uani 1 1 d . . . . .
O1 O 1.11596(9) 0.92156(8) 0.85121(7) 0.0223(4) Uani 1 1 d . . . . .
H1 H 1.1461 0.9046 0.8246 0.033 Uiso 1 1 calc GR . . . .
O2 O 0.78195(10) 0.68208(9) 0.74142(9) 0.0370(5) Uani 1 1 d . . . . .
H2 H 0.7564 0.7183 0.7433 0.056 Uiso 1 1 calc GR . . . .
O3 O 1.06348(11) 0.79414(9) 0.54306(7) 0.0279(4) Uani 1 1 d . . . . .
H3 H 1.0917 0.7656 0.5613 0.042 Uiso 1 1 calc GR . . . .
N1 N 1.04514(11) 0.88046(10) 0.85688(8) 0.0176(4) Uani 1 1 d . . . . .
N2 N 0.85184(12) 0.69178(10) 0.70372(9) 0.0243(5) Uani 1 1 d . . . . .
N3 N 1.06243(12) 0.85627(10) 0.57845(8) 0.0212(5) Uani 1 1 d . . . . .
N4 N 0.99010(10) 0.83659(9) 0.73801(7) 0.0139(4) Uani 1 1 d . . . . .
H4 H 1.0357 0.8331 0.7671 0.017 Uiso 1 1 calc R . . . .
C1 C 0.91654(13) 0.84166(11) 0.77712(10) 0.0162(5) Uani 1 1 d . . . . .
H1a H 0.9140 0.8026 0.8053 0.019 Uiso 1 1 calc R . . . .
H1b H 0.8695 0.8402 0.7501 0.019 Uiso 1 1 calc R . . . .
C2 C 0.91527(14) 0.90594(12) 0.81456(10) 0.0187(5) Uani 1 1 d . . . . .
C3 C 0.84961(14) 0.94758(13) 0.81041(11) 0.0247(6) Uani 1 1 d . . . . .
H3a H 0.8049 0.9331 0.7875 0.030 Uiso 1 1 calc R . . . .
C4 C 0.84825(15) 1.00957(14) 0.83903(13) 0.0352(7) Uani 1 1 d . . . . .
H4a H 0.8026 1.0371 0.8365 0.042 Uiso 1 1 calc R . . . .
C5 C 0.91380(16) 1.03141(14) 0.87151(13) 0.0358(7) Uani 1 1 d . . . . .
H5 H 0.9142 1.0750 0.8895 0.043 Uiso 1 1 calc R . . . .
C6 C 0.97867(15) 0.98982(13) 0.87773(11) 0.0262(6) Uani 1 1 d . . . . .
H6 H 1.0232 1.0048 0.9005 0.031 Uiso 1 1 calc R . . . .
C7 C 0.97928(14) 0.92634(12) 0.85094(10) 0.0187(5) Uani 1 1 d . . . . .
C8 C 1.05052(14) 0.84371(13) 0.91778(10) 0.0228(6) Uani 1 1 d . . . . .
C9 C 0.97598(15) 0.80054(14) 0.92437(11) 0.0293(6) Uani 1 1 d . . . . .
H9a H 0.9292 0.8295 0.9222 0.044 Uiso 1 1 calc GR . . . .
H9b H 0.9770 0.7772 0.9642 0.044 Uiso 1 1 calc GR . . . .
H9c H 0.9741 0.7674 0.8909 0.044 Uiso 1 1 calc GR . . . .
C10 C 1.12184(15) 0.79791(14) 0.91373(11) 0.0287(6) Uani 1 1 d . . . . .
H10a H 1.1185 0.7708 0.8761 0.043 Uiso 1 1 calc GR . . . .
H10b H 1.1231 0.7682 0.9498 0.043 Uiso 1 1 calc GR . . . .
H10c H 1.1700 0.8252 0.9127 0.043 Uiso 1 1 calc GR . . . .
C11 C 1.05863(16) 0.89050(15) 0.97329(11) 0.0345(7) Uani 1 1 d . . . . .
H11a H 1.1039 0.9205 0.9671 0.052 Uiso 1 1 calc GR . . . .
H11b H 1.0667 0.8637 1.0107 0.052 Uiso 1 1 calc GR . . . .
H11c H 1.0105 0.9174 0.9777 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.98977(14) 0.77261(11) 0.70009(9) 0.0166(5) Uani 1 1 d . . . . .
H12a H 0.9436 0.7734 0.6721 0.020 Uiso 1 1 calc R . . . .
H12b H 1.0380 0.7715 0.6743 0.020 Uiso 1 1 calc R . . . .
C13 C 0.98657(14) 0.70963(11) 0.73836(9) 0.0168(5) Uani 1 1 d . . . . .
C14 C 1.05294(15) 0.68876(12) 0.77124(10) 0.0236(6) Uani 1 1 d . . . . .
H14 H 1.1002 0.7143 0.7686 0.028 Uiso 1 1 calc R . . . .
C15 C 1.05121(17) 0.63175(13) 0.80754(11) 0.0314(6) Uani 1 1 d . . . . .
H15 H 1.0969 0.6182 0.8297 0.038 Uiso 1 1 calc R . . . .
C16 C 0.98217(18) 0.59453(13) 0.81129(12) 0.0338(7) Uani 1 1 d . . . . .
H16 H 0.9803 0.5557 0.8368 0.041 Uiso 1 1 calc R . . . .
C17 C 0.91624(16) 0.61344(13) 0.77834(12) 0.0292(6) Uani 1 1 d . . . . .
H17 H 0.8691 0.5877 0.7815 0.035 Uiso 1 1 calc R . . . .
C18 C 0.91823(14) 0.66997(12) 0.74046(10) 0.0205(5) Uani 1 1 d . . . . .
C19 C 0.83861(16) 0.65397(13) 0.64435(12) 0.0307(6) Uani 1 1 d . . . . .
C20 C 0.81509(18) 0.58029(14) 0.65438(14) 0.0445(8) Uani 1 1 d . . . . .
H20a H 0.8594 0.5558 0.6728 0.067 Uiso 1 1 calc GR . . . .
H20b H 0.8013 0.5598 0.6147 0.067 Uiso 1 1 calc GR . . . .
H20c H 0.7695 0.5781 0.6821 0.067 Uiso 1 1 calc GR . . . .
C21 C 0.91405(17) 0.65750(14) 0.60628(11) 0.0346(7) Uani 1 1 d . . . . .
H21a H 0.9268 0.7046 0.5975 0.052 Uiso 1 1 calc GR . . . .
H21b H 0.9065 0.6332 0.5674 0.052 Uiso 1 1 calc GR . . . .
H21c H 0.9575 0.6369 0.6294 0.052 Uiso 1 1 calc GR . . . .
C22 C 0.77287(18) 0.69183(16) 0.61106(14) 0.0487(9) Uani 1 1 d . . . . .
H22a H 0.7238 0.6880 0.6348 0.073 Uiso 1 1 calc GR . . . .
H22b H 0.7652 0.6724 0.5699 0.073 Uiso 1 1 calc GR . . . .
H22c H 0.7874 0.7393 0.6071 0.073 Uiso 1 1 calc GR . . . .
C23 C 1.00611(13) 0.89714(11) 0.69691(10) 0.0164(5) Uani 1 1 d . . . . .
H23a H 0.9984 0.9388 0.7212 0.020 Uiso 1 1 calc R . . . .
H23b H 1.0619 0.8959 0.6833 0.020 Uiso 1 1 calc R . . . .
C24 C 0.95348(13) 0.89946(11) 0.64095(10) 0.0172(5) Uani 1 1 d . . . . .
C25 C 0.87590(15) 0.92210(12) 0.64612(11) 0.0225(6) Uani 1 1 d . . . . .
H25 H 0.8586 0.9413 0.6839 0.027 Uiso 1 1 calc R . . . .
C26 C 0.82371(15) 0.91709(13) 0.59734(11) 0.0274(6) Uani 1 1 d . . . . .
H26 H 0.7710 0.9327 0.6016 0.033 Uiso 1 1 calc R . . . .
C27 C 0.84889(16) 0.88923(13) 0.54241(11) 0.0280(6) Uani 1 1 d . . . . .
H27 H 0.8127 0.8838 0.5093 0.034 Uiso 1 1 calc R . . . .
C28 C 0.92656(16) 0.86928(13) 0.53529(11) 0.0267(6) Uani 1 1 d . . . . .
H28 H 0.9436 0.8510 0.4970 0.032 Uiso 1 1 calc R . . . .
C29 C 0.98015(14) 0.87574(12) 0.58389(10) 0.0194(5) Uani 1 1 d . . . . .
C30 C 1.11624(16) 0.90595(13) 0.54602(10) 0.0258(6) Uani 1 1 d . . . . .
C31 C 1.11041(16) 0.97294(13) 0.57999(11) 0.0298(6) Uani 1 1 d . . . . .
H31a H 1.0564 0.9903 0.5768 0.045 Uiso 1 1 calc GR . . . .
H31b H 1.1471 1.0052 0.5615 0.045 Uiso 1 1 calc GR . . . .
H31c H 1.1239 0.9664 0.6235 0.045 Uiso 1 1 calc GR . . . .
C32 C 1.09484(17) 0.91571(14) 0.47792(11) 0.0355(7) Uani 1 1 d . . . . .
H32a H 1.0437 0.9385 0.4748 0.053 Uiso 1 1 calc GR . . . .
H32b H 1.0917 0.8718 0.4576 0.053 Uiso 1 1 calc GR . . . .
H32c H 1.1354 0.9431 0.4578 0.053 Uiso 1 1 calc GR . . . .
C33 C 1.19968(16) 0.87877(14) 0.55243(11) 0.0313(6) Uani 1 1 d . . . . .
H33a H 1.2370 0.9106 0.5340 0.047 Uiso 1 1 calc GR . . . .
H33b H 1.2036 0.8354 0.5312 0.047 Uiso 1 1 calc GR . . . .
H33c H 1.2122 0.8727 0.5962 0.047 Uiso 1 1 calc GR . . . .
O4 O 0.84030(10) 1.22385(9) 0.87805(8) 0.0297(4) Uani 1 1 d . . . . .
H4b H 0.8286 1.2517 0.8503 0.045 Uiso 1 1 calc GR . . . .
C34 C 0.77670(15) 1.17811(13) 0.88637(12) 0.0303(6) Uani 1 1 d . . . . .
H34a H 0.7903 1.1461 0.9197 0.036 Uiso 1 1 calc R . . . .
H34b H 0.7691 1.1520 0.8479 0.036 Uiso 1 1 calc R . . . .
C35 C 0.70052(16) 1.21309(15) 0.90254(13) 0.0405(7) Uani 1 1 d . . . . .
H35a H 0.6879 1.2463 0.8706 0.061 Uiso 1 1 calc GR . . . .
H35b H 0.7062 1.2358 0.9424 0.061 Uiso 1 1 calc GR . . . .
H35c H 0.6579 1.1799 0.9051 0.061 Uiso 1 1 calc GR . . . .


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 N1 1.457(2) . ?
O2 N2 1.451(2) . ?
O3 N3 1.454(2) . ?
N1 C7 1.447(3) . ?
N1 C8 1.511(3) . ?
N2 C18 1.445(3) . ?
N2 C19 1.507(3) . ?
N3 C29 1.451(3) . ?
N3 C30 1.516(3) . ?
N4 C1 1.510(3) . ?
N4 C12 1.514(3) . ?
N4 C23 1.522(3) . ?
C1 C2 1.514(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.401(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.385(4) . ?
C5 C6 1.382(4) . ?
C6 C7 1.389(3) . ?
C8 C9 1.533(3) . ?
C8 C10 1.515(4) . ?
C8 C11 1.527(3) . ?
C12 C13 1.503(3) . ?
C13 C14 1.394(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.386(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.392(3) . ?
C19 C20 1.533(4) . ?
C19 C21 1.523(4) . ?
C19 C22 1.525(4) . ?
C23 C24 1.506(3) . ?
C24 C25 1.394(3) . ?
C24 C29 1.399(3) . ?
C25 C26 1.382(3) . ?
C26 C27 1.381(3) . ?
C27 C28 1.383(3) . ?
C28 C29 1.397(3) . ?
C30 C31 1.525(3) . ?
C30 C32 1.532(3) . ?
C30 C33 1.520(3) . ?
O4 C34 1.421(3) . ?
C34 C35 1.507(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C8 107.16(16) . . ?
C7 N1 O1 105.91(17) . . ?
C7 N1 C8 115.40(17) . . ?
O2 N2 C19 107.05(18) . . ?
C18 N2 O2 106.55(18) . . ?
C18 N2 C19 115.91(19) . . ?
O3 N3 C30 107.53(17) . . ?
C29 N3 O3 106.32(17) . . ?
C29 N3 C30 116.18(19) . . ?
C1 N4 C12 110.95(16) . . ?
C1 N4 C23 115.01(17) . . ?
C12 N4 C23 110.32(15) . . ?
N4 C1 C2 111.65(18) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C7 118.9(2) . . ?
C7 C2 C1 122.4(2) . . ?
C4 C3 C2 121.1(2) . . ?
C3 C4 C5 119.7(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C6 C7 120.6(2) . . ?
C2 C7 N1 117.7(2) . . ?
C6 C7 N1 122.8(2) . . ?
C6 C7 C2 119.5(2) . . ?
N1 C8 C9 107.59(18) . . ?
N1 C8 C10 106.72(18) . . ?
N1 C8 C11 113.5(2) . . ?
C10 C8 C9 109.0(2) . . ?
C10 C8 C11 109.9(2) . . ?
C11 C8 C9 110.0(2) . . ?
C13 C12 N4 113.59(16) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 C18 118.8(2) . . ?
C18 C13 C12 121.1(2) . . ?
C15 C14 C13 121.2(2) . . ?
C14 C15 C16 119.3(2) . . ?
C17 C16 C15 120.5(2) . . ?
C16 C17 C18 120.4(2) . . ?
C13 C18 N2 117.2(2) . . ?
C17 C18 N2 123.3(2) . . ?
C17 C18 C13 119.6(2) . . ?
N2 C19 C20 113.2(2) . . ?
N2 C19 C21 108.4(2) . . ?
N2 C19 C22 105.5(2) . . ?
C21 C19 C20 109.8(2) . . ?
C21 C19 C22 109.5(2) . . ?
C22 C19 C20 110.4(2) . . ?
C24 C23 N4 112.96(18) . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 C29 119.0(2) . . ?
C29 C24 C23 120.7(2) . . ?
C26 C25 C24 121.2(2) . . ?
C27 C26 C25 119.4(2) . . ?
C26 C27 C28 120.3(2) . . ?
C27 C28 C29 120.5(2) . . ?
C24 C29 N3 118.2(2) . . ?
C28 C29 N3 122.6(2) . . ?
C28 C29 C24 119.2(2) . . ?
N3 C30 C31 107.82(18) . . ?
N3 C30 C32 112.8(2) . . ?
N3 C30 C33 106.6(2) . . ?
C31 C30 C32 109.8(2) . . ?
C33 C30 C31 109.1(2) . . ?
C33 C30 C32 110.7(2) . . ?
O4 C34 C35 112.5(2) . . ?
####################################################################### 
# 
# 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_40229
_database_code_depnum_ccdc_archive 'CCDC 1901558'
loop_
_audit_author_name
_audit_author_address
'Patrick J. Carroll'
;University of Pennsylvania
United States of America
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

# Crystallographer: Patrick J. Carroll

_audit_creation_date             2017-12-27
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.12.21 svn.r3473 for OlexSys, GUI svn.r5450)
;
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         '2(I), 2(C33 H49 N4 O3), C2 H6 O'
_chemical_formula_sum            'C68 H104 I2 N8 O7'
_chemical_formula_weight         1399.39

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.8928(4)
_cell_length_b                   34.9965(14)
_cell_length_c                   20.5965(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.4500(10)
_cell_angle_gamma                90
_cell_volume                     7130.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9670
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             2920
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            57042
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         1.978
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_number_gt                13979
_reflns_number_total             16335
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.315
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         16335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.072
_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)+(0.0548P)²+12.9049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1243
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

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
I1 I 0.67438(2) 0.53778(2) 0.30287(2) 0.03104(7) Uani 1 1 d . . . . .
O1 O 0.5595(5) 0.48354(12) 0.42909(16) 0.0861(14) Uani 1 1 d . . . . .
H1 H 0.565546 0.497806 0.396442 0.129 Uiso 1 1 calc GR . . . .
O2 O 1.0359(2) 0.33587(6) 0.25022(13) 0.0363(6) Uani 1 1 d . . . . .
H2 H 0.969223 0.321992 0.259092 0.054 Uiso 1 1 calc GR . . . .
O3 O 0.6372(2) 0.47484(7) 0.08052(11) 0.0322(5) Uani 1 1 d . . . . .
H3 H 0.699514 0.489717 0.092054 0.048 Uiso 1 1 calc GR . . . .
N1 N 0.6637(4) 0.45311(11) 0.42555(15) 0.0527(9) Uani 1 1 d . . . . .
N2 N 0.9890(2) 0.37101(7) 0.22081(12) 0.0208(5) Uani 1 1 d . . . . .
N3 N 0.5547(2) 0.46543(7) 0.13624(12) 0.0218(5) Uani 1 1 d . . . . .
N4 N 0.7079(2) 0.42857(7) 0.29450(11) 0.0211(5) Uani 1 1 d . . . . .
H4 H 0.715828 0.450647 0.325120 0.028 Uiso 1 1 calc R . . . .
C1 C 0.7300(3) 0.39339(10) 0.33437(15) 0.0308(7) Uani 1 1 d . . . . .
H1a H 0.819951 0.394628 0.355625 0.041 Uiso 1 1 calc R . . . .
H1b H 0.728108 0.370645 0.305804 0.041 Uiso 1 1 calc R . . . .
C2 C 0.6209(4) 0.38958(13) 0.38598(18) 0.0444(9) Uani 1 1 d . . . . .
C3 C 0.5495(5) 0.35518(16) 0.3890(2) 0.0596(13) Uani 1 1 d . . . . .
H5 H 0.573516 0.334365 0.361786 0.079 Uiso 1 1 calc R . . . .
C4 C 0.4417(5) 0.3517(2) 0.4327(3) 0.081(2) Uani 1 1 d . . . . .
H6 H 0.394137 0.328230 0.435803 0.107 Uiso 1 1 calc R . . . .
C5 C 0.4042(6) 0.3822(3) 0.4712(3) 0.091(2) Uani 1 1 d . . . . .
H7 H 0.328985 0.380075 0.499404 0.122 Uiso 1 1 calc R . . . .
C6 C 0.4740(5) 0.4145(2) 0.4686(2) 0.0756(18) Uani 1 1 d . . . . .
H8 H 0.447525 0.435430 0.495013 0.101 Uiso 1 1 calc R . . . .
C7 C 0.5862(4) 0.41871(14) 0.42769(18) 0.0499(10) Uani 1 1 d . . . . .
C8 C 0.7595(6) 0.45899(15) 0.4813(2) 0.0660(14) Uani 1 1 d . . . . .
C9 C 0.8700(5) 0.42794(14) 0.4765(2) 0.0566(11) Uani 1 1 d . . . . .
H9a H 0.919730 0.431174 0.435940 0.085 Uiso 1 1 calc GR . . . .
H9b H 0.827752 0.402617 0.477199 0.085 Uiso 1 1 calc GR . . . .
H9c H 0.932556 0.430342 0.513430 0.085 Uiso 1 1 calc GR . . . .
C10 C 0.6882(8) 0.4558(2) 0.5483(2) 0.097(2) Uani 1 1 d . . . . .
H10a H 0.755283 0.458616 0.583205 0.145 Uiso 1 1 calc GR . . . .
H10b H 0.644410 0.430749 0.551813 0.145 Uiso 1 1 calc GR . . . .
H10c H 0.619950 0.475951 0.551961 0.145 Uiso 1 1 calc GR . . . .
C11 C 0.8209(8) 0.49847(16) 0.4733(3) 0.093(2) Uani 1 1 d . . . . .
H11a H 0.852901 0.501549 0.428727 0.139 Uiso 1 1 calc GR . . . .
H11b H 0.897104 0.501425 0.503636 0.139 Uiso 1 1 calc GR . . . .
H11c H 0.752437 0.517926 0.482520 0.139 Uiso 1 1 calc GR . . . .
C12 C 0.8155(3) 0.43452(8) 0.24337(13) 0.0212(6) Uani 1 1 d . . . . .
H12a H 0.806477 0.414422 0.209792 0.028 Uiso 1 1 calc R . . . .
H12b H 0.800740 0.459542 0.222047 0.028 Uiso 1 1 calc R . . . .
C13 C 0.9564(3) 0.43337(8) 0.27133(13) 0.0207(5) Uani 1 1 d . . . . .
C14 C 1.0032(3) 0.46397(10) 0.30866(16) 0.0321(7) Uani 1 1 d . . . . .
H14 H 0.949167 0.486253 0.312908 0.043 Uiso 1 1 calc R . . . .
C15 C 1.1266(4) 0.46212(11) 0.33924(17) 0.0392(8) Uani 1 1 d . . . . .
H15 H 1.158467 0.483171 0.364135 0.052 Uiso 1 1 calc R . . . .
C16 C 1.2046(3) 0.42949(12) 0.33373(15) 0.0372(8) Uani 1 1 d . . . . .
H16 H 1.287663 0.427689 0.356955 0.049 Uiso 1 1 calc R . . . .
C17 C 1.1627(3) 0.39925(10) 0.29454(14) 0.0280(7) Uani 1 1 d . . . . .
H17 H 1.218062 0.377241 0.290155 0.037 Uiso 1 1 calc R . . . .
C18 C 1.0390(3) 0.40140(8) 0.26171(13) 0.0200(5) Uani 1 1 d . . . . .
C19 C 1.0391(3) 0.37118(9) 0.15192(15) 0.0266(6) Uani 1 1 d . . . . .
C20 C 0.9981(4) 0.40880(10) 0.11935(15) 0.0336(7) Uani 1 1 d . . . . .
H20a H 0.899390 0.411003 0.118753 0.050 Uiso 1 1 calc GR . . . .
H20b H 1.031837 0.409231 0.074740 0.050 Uiso 1 1 calc GR . . . .
H20c H 1.037015 0.430259 0.143711 0.050 Uiso 1 1 calc GR . . . .
C21 C 0.9680(4) 0.33784(12) 0.1179(2) 0.0445(9) Uani 1 1 d . . . . .
H21a H 0.996048 0.313746 0.138129 0.067 Uiso 1 1 calc GR . . . .
H21b H 0.992464 0.337611 0.071859 0.067 Uiso 1 1 calc GR . . . .
H21c H 0.869879 0.340804 0.121806 0.067 Uiso 1 1 calc GR . . . .
C22 C 1.1922(3) 0.36626(10) 0.14760(17) 0.0324(7) Uani 1 1 d . . . . .
H22a H 1.237166 0.387486 0.170072 0.049 Uiso 1 1 calc GR . . . .
H22b H 1.219111 0.366061 0.101911 0.049 Uiso 1 1 calc GR . . . .
H22c H 1.218629 0.342074 0.168060 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.5681(3) 0.43167(9) 0.26299(14) 0.0228(6) Uani 1 1 d . . . . .
H23a H 0.499142 0.423820 0.294888 0.030 Uiso 1 1 calc R . . . .
H23b H 0.550760 0.458703 0.251463 0.030 Uiso 1 1 calc R . . . .
C24 C 0.5531(3) 0.40742(8) 0.20283(14) 0.0214(6) Uani 1 1 d . . . . .
C25 C 0.5471(3) 0.36767(9) 0.20757(16) 0.0270(6) Uani 1 1 d . . . . .
H25 H 0.538399 0.356173 0.249108 0.036 Uiso 1 1 calc R . . . .
C26 C 0.5536(3) 0.34474(9) 0.15333(17) 0.0297(7) Uani 1 1 d . . . . .
H26 H 0.551389 0.317722 0.157581 0.039 Uiso 1 1 calc R . . . .
C27 C 0.5635(3) 0.36137(9) 0.09259(16) 0.0287(7) Uani 1 1 d . . . . .
H27 H 0.571590 0.345722 0.055134 0.038 Uiso 1 1 calc R . . . .
C28 C 0.5616(3) 0.40093(9) 0.08625(15) 0.0251(6) Uani 1 1 d . . . . .
H28 H 0.565032 0.412081 0.044242 0.033 Uiso 1 1 calc R . . . .
C29 C 0.5547(3) 0.42442(8) 0.14081(13) 0.0205(5) Uani 1 1 d . . . . .
C30 C 0.4179(3) 0.48344(9) 0.12507(15) 0.0250(6) Uani 1 1 d . . . . .
C31 C 0.3311(3) 0.47685(10) 0.18493(15) 0.0277(6) Uani 1 1 d . . . . .
H31a H 0.321734 0.449346 0.192589 0.041 Uiso 1 1 calc GR . . . .
H31b H 0.241577 0.488152 0.177890 0.041 Uiso 1 1 calc GR . . . .
H31c H 0.374344 0.488825 0.222769 0.041 Uiso 1 1 calc GR . . . .
C32 C 0.4413(4) 0.52650(9) 0.11830(18) 0.0364(8) Uani 1 1 d . . . . .
H32a H 0.497468 0.535533 0.154591 0.055 Uiso 1 1 calc GR . . . .
H32b H 0.354188 0.539808 0.118716 0.055 Uiso 1 1 calc GR . . . .
H32c H 0.487326 0.531714 0.077278 0.055 Uiso 1 1 calc GR . . . .
C33 C 0.3449(4) 0.46796(10) 0.06462(16) 0.0323(7) Uani 1 1 d . . . . .
H33a H 0.403955 0.470448 0.026857 0.048 Uiso 1 1 calc GR . . . .
H33b H 0.261744 0.482559 0.057114 0.048 Uiso 1 1 calc GR . . . .
H33c H 0.322480 0.440973 0.071243 0.048 Uiso 1 1 calc GR . . . .
I1' I 0.76061(2) 0.27878(2) 0.28659(2) 0.04455(8) Uani 1 1 d . . . . .
O1' O 0.6844(3) 0.18264(9) 0.32349(17) 0.0319(7) Uani 0.73 1 d . . P A 1
H1' H 0.695341 0.206390 0.320961 0.048 Uiso 0.73 1 calc GR . P A 1
O2' O 0.4765(4) 0.24783(11) 0.36427(19) 0.0295(8) Uani 0.6 1 d . . P B 1
H2' H 0.544913 0.252356 0.341610 0.044 Uiso 0.6 1 calc GR . P B 1
O1" O 0.8819(8) 0.1939(2) 0.3092(5) 0.0305(18) Uani 0.27 1 d . . P A 2
H1" H 0.830897 0.210688 0.293133 0.046 Uiso 0.27 1 calc GR . P A 2
O2" O 0.4646(6) 0.22105(17) 0.2778(3) 0.0373(14) Uani 0.4 1 d . . P B 2
H2" H 0.528629 0.236760 0.279987 0.056 Uiso 0.4 1 calc GR . P B 2
O3' O 0.6559(3) 0.20416(8) 0.18505(14) 0.0509(7) Uani 1 1 d . . . . .
H3' H 0.698208 0.221262 0.205365 0.076 Uiso 1 1 calc GR . . . .
N1' N 0.8091(3) 0.16489(8) 0.32905(14) 0.0319(6) Uani 1 1 d . . . . .
N2' N 0.3851(3) 0.22549(8) 0.32853(14) 0.0305(6) Uani 1 1 d . . . . .
N3' N 0.6012(4) 0.21972(9) 0.12651(15) 0.0424(7) Uani 1 1 d . . . . .
N4' N 0.5000(2) 0.14627(7) 0.24429(11) 0.0195(5) Uani 1 1 d . . . . .
H4' H 0.544800 0.171275 0.253818 0.026 Uiso 1 1 calc R . . . .
C1' C 0.5782(3) 0.11515(8) 0.27892(14) 0.0216(6) Uani 1 1 d . . . . .
H1a' H 0.575890 0.120156 0.326204 0.029 Uiso 1 1 calc R . . . .
H1b' H 0.532540 0.090401 0.270992 0.029 Uiso 1 1 calc R . . . .
C2' C 0.7238(3) 0.11178(9) 0.25828(15) 0.0238(6) Uani 1 1 d . . . . .
C3' C 0.7573(3) 0.08267(10) 0.21518(17) 0.0340(7) Uani 1 1 d . . . . .
H9 H 0.688245 0.066048 0.199814 0.045 Uiso 1 1 calc R . . . .
C4' C 0.8896(4) 0.07724(11) 0.19395(18) 0.0383(8) Uani 1 1 d . . . . .
H10 H 0.910024 0.057038 0.164818 0.051 Uiso 1 1 calc R . . . .
C5' C 0.9886(4) 0.10102(11) 0.21523(18) 0.0388(8) Uani 1 1 d . . . . .
H5' H 1.078404 0.097878 0.200091 0.052 Uiso 1 1 calc R . . . .
C6' C 0.9596(3) 0.12975(10) 0.25876(17) 0.0338(7) Uani 1 1 d . . . . .
H6' H 1.029789 0.146366 0.272909 0.045 Uiso 1 1 calc R . . . .
C7' C 0.8278(3) 0.13496(9) 0.28266(15) 0.0250(6) Uani 1 1 d . . . . .
C8' C 0.8345(3) 0.15576(9) 0.39950(16) 0.0294(7) Uani 1 1 d . . . . .
C9' C 0.8116(6) 0.19211(13) 0.4370(2) 0.0617(13) Uani 1 1 d . . . . .
H9a' H 0.872575 0.212027 0.421135 0.092 Uiso 1 1 calc GR . . . .
H9b' H 0.829585 0.187533 0.483251 0.092 Uiso 1 1 calc GR . . . .
H9c' H 0.717672 0.200419 0.431171 0.092 Uiso 1 1 calc GR . . . .
C10' C 0.9817(4) 0.14328(11) 0.40869(18) 0.0392(8) Uani 1 1 d . . . . .
H10a' H 0.996966 0.119337 0.385175 0.059 Uiso 1 1 calc GR . . . .
H10b' H 1.000488 0.139384 0.455003 0.059 Uiso 1 1 calc GR . . . .
H10c' H 1.041790 0.163112 0.391770 0.059 Uiso 1 1 calc GR . . . .
C11' C 0.7442(4) 0.12409(12) 0.42371(18) 0.0416(9) Uani 1 1 d . . . . .
H11a' H 0.649611 0.132351 0.421227 0.062 Uiso 1 1 calc GR . . . .
H11b' H 0.767808 0.118082 0.468859 0.062 Uiso 1 1 calc GR . . . .
H11c' H 0.756488 0.101306 0.396739 0.062 Uiso 1 1 calc GR . . . .
C12' C 0.3573(3) 0.14790(9) 0.26974(14) 0.0227(6) Uani 1 1 d . . . . .
H12a' H 0.307269 0.168101 0.246003 0.030 Uiso 1 1 calc R . . . .
H12b' H 0.312141 0.123246 0.260322 0.030 Uiso 1 1 calc R . . . .
C13' C 0.3481(3) 0.15574(8) 0.34142(14) 0.0208(6) Uani 1 1 d . . . . .
C14' C 0.3257(3) 0.12490(9) 0.38341(16) 0.0289(7) Uani 1 1 d . . . . .
H14' H 0.317300 0.099863 0.366028 0.038 Uiso 1 1 calc R . . . .
C15' C 0.3155(3) 0.13032(11) 0.44986(16) 0.0343(8) Uani 1 1 d . . . . .
H15' H 0.300635 0.109118 0.477719 0.046 Uiso 1 1 calc R . . . .
C16' C 0.3271(3) 0.16663(11) 0.47535(16) 0.0351(8) Uani 1 1 d . . . . .
H16' H 0.319795 0.170457 0.520856 0.047 Uiso 1 1 calc R . . . .
C17' C 0.3490(3) 0.19722(10) 0.43517(15) 0.0300(7) Uani 1 1 d . . . . .
H17' H 0.358381 0.222019 0.453422 0.040 Uiso 1 1 calc R . . . .
C18' C 0.3580(3) 0.19267(9) 0.36814(14) 0.0224(6) Uani 1 1 d . . . . .
C19' C 0.2650(3) 0.25040(9) 0.30956(18) 0.0330(7) Uani 1 1 d . . . . .
C20' C 0.3239(5) 0.28388(13) 0.2717(3) 0.0642(14) Uani 1 1 d . . . . .
H20a' H 0.376585 0.300174 0.301145 0.096 Uiso 1 1 calc GR . . . .
H20b' H 0.250272 0.298808 0.252179 0.096 Uiso 1 1 calc GR . . . .
H20c' H 0.382712 0.274147 0.237350 0.096 Uiso 1 1 calc GR . . . .
C21' C 0.1881(4) 0.26430(12) 0.3686(2) 0.0484(10) Uani 1 1 d . . . . .
H21a' H 0.146340 0.242447 0.390471 0.073 Uiso 1 1 calc GR . . . .
H21b' H 0.117586 0.282294 0.354832 0.073 Uiso 1 1 calc GR . . . .
H21c' H 0.250636 0.277102 0.398643 0.073 Uiso 1 1 calc GR . . . .
C22' C 0.1698(4) 0.22831(12) 0.2657(2) 0.0437(9) Uani 1 1 d . . . . .
H22a' H 0.217398 0.220767 0.226159 0.066 Uiso 1 1 calc GR . . . .
H22b' H 0.092290 0.244427 0.254153 0.066 Uiso 1 1 calc GR . . . .
H22c' H 0.138141 0.205420 0.288375 0.066 Uiso 1 1 calc GR . . . .
C23' C 0.5000(3) 0.14022(9) 0.17153(14) 0.0247(6) Uani 1 1 d . . . . .
H23a' H 0.594445 0.140922 0.156014 0.033 Uiso 1 1 calc R . . . .
H23b' H 0.463114 0.114540 0.161819 0.033 Uiso 1 1 calc R . . . .
C24' C 0.4183(3) 0.16970(10) 0.13480(14) 0.0285(7) Uani 1 1 d . . . . .
C25' C 0.2847(4) 0.16019(12) 0.11856(16) 0.0389(8) Uani 1 1 d . . . . .
H25' H 0.251226 0.135650 0.129903 0.052 Uiso 1 1 calc R . . . .
C26' C 0.2003(4) 0.18544(16) 0.08659(19) 0.0539(12) Uani 1 1 d . . . . .
H26' H 0.110462 0.178178 0.075510 0.072 Uiso 1 1 calc R . . . .
C27' C 0.2472(5) 0.22112(16) 0.0709(2) 0.0589(13) Uani 1 1 d . . . . .
H27' H 0.189322 0.238876 0.049638 0.078 Uiso 1 1 calc R . . . .
C28' C 0.3787(5) 0.23124(13) 0.08614(19) 0.0497(10) Uani 1 1 d . . . . .
H28' H 0.409769 0.256156 0.075627 0.066 Uiso 1 1 calc R . . . .
C29' C 0.4672(4) 0.20558(10) 0.11671(16) 0.0349(7) Uani 1 1 d . . . . .
C30' C 0.7023(4) 0.21306(12) 0.0729(2) 0.0449(9) Uani 1 1 d . . . . .
C31' C 0.8280(5) 0.23558(16) 0.0913(3) 0.0672(14) Uani 1 1 d . . . . .
H31a' H 0.803113 0.262161 0.100220 0.101 Uiso 1 1 calc GR . . . .
H31b' H 0.892407 0.234787 0.055452 0.101 Uiso 1 1 calc GR . . . .
H31c' H 0.869595 0.224323 0.130206 0.101 Uiso 1 1 calc GR . . . .
C32' C 0.6437(5) 0.23020(14) 0.0101(2) 0.0576(12) Uani 1 1 d . . . . .
H32a' H 0.562378 0.216006 -0.002735 0.086 Uiso 1 1 calc GR . . . .
H32b' H 0.710971 0.228461 -0.024440 0.086 Uiso 1 1 calc GR . . . .
H32c' H 0.620320 0.257058 0.017413 0.086 Uiso 1 1 calc GR . . . .
C33' C 0.7344(5) 0.17088(12) 0.0632(2) 0.0501(10) Uani 1 1 d . . . . .
H33a' H 0.772002 0.160267 0.103459 0.075 Uiso 1 1 calc GR . . . .
H33b' H 0.800436 0.168115 0.028248 0.075 Uiso 1 1 calc GR . . . .
H33c' H 0.651423 0.157127 0.051480 0.075 Uiso 1 1 calc GR . . . .
C34 C 0.9837(4) 0.52945(13) 0.0756(2) 0.0470(9) Uani 1 1 d . . . . .
H34a H 0.957967 0.504621 0.057303 0.071 Uiso 1 1 calc GR . . . .
H34b H 1.082067 0.532443 0.073573 0.071 Uiso 1 1 calc GR . . . .
H34c H 0.939999 0.549901 0.050649 0.071 Uiso 1 1 calc GR . . . .
C35 C 0.9398(4) 0.53153(11) 0.14435(18) 0.0374(8) Uani 1 1 d . . . . .
H35a H 0.983812 0.511021 0.170021 0.050 Uiso 1 1 calc R . . . .
H35b H 0.965923 0.556465 0.163365 0.050 Uiso 1 1 calc R . . . .
O4 O 0.7974(3) 0.52715(8) 0.14581(13) 0.0434(6) Uani 1 1 d . . . . .
H4a H 0.770772 0.528505 0.184367 0.065 Uiso 1 1 calc GR . . . .


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 N1 1.484(5) . ?
O2 N2 1.446(3) . ?
O3 N3 1.451(3) . ?
N1 C7 1.428(6) . ?
N1 C8 1.497(6) . ?
N2 C18 1.442(4) . ?
N2 C19 1.507(4) . ?
N3 C29 1.438(4) . ?
N3 C30 1.508(4) . ?
N4 C1 1.495(4) . ?
N4 C12 1.518(4) . ?
N4 C23 1.527(4) . ?
C1 C2 1.526(5) . ?
C2 C3 1.397(6) . ?
C2 C7 1.378(6) . ?
C3 C4 1.407(7) . ?
C4 C5 1.382(10) . ?
C5 C6 1.326(10) . ?
C6 C7 1.406(6) . ?
C8 C9 1.545(7) . ?
C8 C10 1.559(7) . ?
C8 C11 1.519(8) . ?
C12 C13 1.504(4) . ?
C13 C14 1.395(4) . ?
C13 C18 1.400(4) . ?
C14 C15 1.371(5) . ?
C15 C16 1.383(6) . ?
C16 C17 1.392(5) . ?
C17 C18 1.395(4) . ?
C19 C20 1.531(5) . ?
C19 C21 1.530(4) . ?
C19 C22 1.528(4) . ?
C23 C24 1.508(4) . ?
C24 C25 1.396(4) . ?
C24 C29 1.410(4) . ?
C25 C26 1.377(5) . ?
C26 C27 1.384(5) . ?
C27 C28 1.391(4) . ?
C28 C29 1.395(4) . ?
C30 C31 1.526(4) . ?
C30 C32 1.531(4) . ?
C30 C33 1.533(4) . ?
O1' N1' 1.385(4) . ?
O2' N2' 1.400(4) . ?
O1" N1' 1.313(8) . ?
O2" N2' 1.322(7) . ?
O3' N3' 1.426(4) . ?
N1' C7' 1.431(4) . ?
N1' C8' 1.505(4) . ?
N2' C18' 1.435(4) . ?
N2' C19' 1.522(4) . ?
N3' C29' 1.428(5) . ?
N3' C30' 1.513(5) . ?
N4' C1' 1.512(3) . ?
N4' C12' 1.511(4) . ?
N4' C23' 1.513(4) . ?
C1' C2' 1.509(4) . ?
C2' C3' 1.393(4) . ?
C2' C7' 1.400(4) . ?
C3' C4' 1.396(5) . ?
C4' C5' 1.356(5) . ?
C5' C6' 1.379(5) . ?
C6' C7' 1.409(4) . ?
C8' C9' 1.507(5) . ?
C8' C10' 1.530(5) . ?
C8' C11' 1.511(5) . ?
C12' C13' 1.505(4) . ?
C13' C14' 1.402(4) . ?
C13' C18' 1.408(4) . ?
C14' C15' 1.386(5) . ?
C15' C16' 1.379(5) . ?
C16' C17' 1.372(5) . ?
C17' C18' 1.393(4) . ?
C19' C20' 1.526(5) . ?
C19' C21' 1.520(5) . ?
C19' C22' 1.512(5) . ?
C23' C24' 1.510(4) . ?
C24' C25' 1.402(5) . ?
C24' C29' 1.397(5) . ?
C25' C26' 1.380(6) . ?
C26' C27' 1.372(7) . ?
C27' C28' 1.382(7) . ?
C28' C29' 1.400(5) . ?
C30' C31' 1.517(6) . ?
C30' C32' 1.536(6) . ?
C30' C33' 1.523(6) . ?
C34 C35 1.486(5) . ?
C35 O4 1.418(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C8 107.4(4) . . ?
C7 N1 O1 103.3(4) . . ?
C7 N1 C8 115.4(3) . . ?
O2 N2 C19 106.9(2) . . ?
C18 N2 O2 106.0(2) . . ?
C18 N2 C19 115.7(2) . . ?
O3 N3 C30 107.1(2) . . ?
C29 N3 O3 106.2(2) . . ?
C29 N3 C30 115.2(2) . . ?
C1 N4 C12 113.2(2) . . ?
C1 N4 C23 114.8(2) . . ?
C12 N4 C23 109.5(2) . . ?
N4 C1 C2 110.7(3) . . ?
C3 C2 C1 117.8(4) . . ?
C7 C2 C1 123.4(4) . . ?
C7 C2 C3 118.8(4) . . ?
C2 C3 C4 119.2(6) . . ?
C5 C4 C3 120.6(6) . . ?
C6 C5 C4 119.5(5) . . ?
C5 C6 C7 121.8(6) . . ?
C2 C7 N1 117.9(4) . . ?
C2 C7 C6 119.9(5) . . ?
C6 C7 N1 122.2(5) . . ?
N1 C8 C9 107.4(4) . . ?
N1 C8 C10 112.4(5) . . ?
N1 C8 C11 107.1(4) . . ?
C9 C8 C10 109.3(4) . . ?
C11 C8 C9 110.4(5) . . ?
C11 C8 C10 110.2(5) . . ?
C13 C12 N4 112.6(2) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 C18 120.0(3) . . ?
C18 C13 C12 120.5(2) . . ?
C15 C14 C13 120.5(3) . . ?
C14 C15 C16 119.8(3) . . ?
C15 C16 C17 120.8(3) . . ?
C16 C17 C18 119.7(3) . . ?
C13 C18 N2 118.3(2) . . ?
C17 C18 N2 122.6(3) . . ?
C17 C18 C13 119.0(3) . . ?
N2 C19 C20 109.2(2) . . ?
N2 C19 C21 106.0(3) . . ?
N2 C19 C22 112.8(3) . . ?
C21 C19 C20 109.6(3) . . ?
C22 C19 C20 109.3(3) . . ?
C22 C19 C21 109.9(3) . . ?
C24 C23 N4 113.1(2) . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 C29 119.0(3) . . ?
C29 C24 C23 120.3(3) . . ?
C26 C25 C24 121.4(3) . . ?
C25 C26 C27 119.5(3) . . ?
C26 C27 C28 120.2(3) . . ?
C27 C28 C29 120.8(3) . . ?
C24 C29 N3 118.7(2) . . ?
C28 C29 N3 122.4(3) . . ?
C28 C29 C24 118.8(3) . . ?
N3 C30 C31 108.9(2) . . ?
N3 C30 C32 106.8(3) . . ?
N3 C30 C33 113.1(2) . . ?
C31 C30 C32 108.0(3) . . ?
C31 C30 C33 109.8(3) . . ?
C32 C30 C33 110.2(3) . . ?
O1' N1' C7' 113.1(3) . . ?
O1' N1' C8' 108.5(3) . . ?
O1" N1' C7' 106.5(4) . . ?
O1" N1' C8' 112.1(5) . . ?
C7' N1' C8' 117.8(2) . . ?
O2' N2' C18' 105.7(3) . . ?
O2' N2' C19' 108.4(3) . . ?
O2" N2' C18' 118.0(3) . . ?
O2" N2' C19' 109.4(4) . . ?
C18' N2' C19' 117.1(2) . . ?
O3' N3' C29' 109.4(3) . . ?
O3' N3' C30' 108.0(3) . . ?
C29' N3' C30' 117.5(3) . . ?
C1' N4' C23' 111.2(2) . . ?
C12' N4' C1' 109.9(2) . . ?
C12' N4' C23' 110.9(2) . . ?
C2' C1' N4' 114.2(2) . . ?
C3' C2' C1' 118.0(3) . . ?
C3' C2' C7' 118.3(3) . . ?
C7' C2' C1' 123.6(3) . . ?
C2' C3' C4' 121.9(3) . . ?
C5' C4' C3' 119.5(3) . . ?
C4' C5' C6' 120.3(3) . . ?
C5' C6' C7' 121.3(3) . . ?
C2' C7' N1' 124.4(3) . . ?
C2' C7' C6' 118.6(3) . . ?
C6' C7' N1' 116.9(3) . . ?
N1' C8' C9' 106.9(3) . . ?
N1' C8' C10' 109.4(3) . . ?
N1' C8' C11' 112.3(3) . . ?
C9' C8' C10' 108.9(3) . . ?
C9' C8' C11' 111.0(3) . . ?
C11' C8' C10' 108.3(3) . . ?
C13' C12' N4' 114.3(2) . . ?
C14' C13' C12' 118.4(3) . . ?
C14' C13' C18' 118.5(3) . . ?
C18' C13' C12' 123.1(3) . . ?
C15' C14' C13' 121.1(3) . . ?
C16' C15' C14' 119.7(3) . . ?
C17' C16' C15' 120.2(3) . . ?
C16' C17' C18' 121.3(3) . . ?
C13' C18' N2' 121.7(3) . . ?
C17' C18' N2' 119.0(3) . . ?
C17' C18' C13' 119.2(3) . . ?
N2' C19' C20' 105.7(3) . . ?
C21' C19' N2' 111.9(3) . . ?
C21' C19' C20' 111.1(4) . . ?
C22' C19' N2' 110.0(3) . . ?
C22' C19' C20' 109.0(4) . . ?
C22' C19' C21' 109.2(3) . . ?
C24' C23' N4' 113.3(2) . . ?
C25' C24' C23' 117.2(3) . . ?
C29' C24' C23' 124.2(3) . . ?
C29' C24' C25' 118.5(3) . . ?
C26' C25' C24' 121.9(4) . . ?
C27' C26' C25' 119.4(4) . . ?
C26' C27' C28' 120.0(4) . . ?
C27' C28' C29' 121.4(4) . . ?
C24' C29' N3' 126.6(3) . . ?
C24' C29' C28' 118.7(4) . . ?
C28' C29' N3' 114.7(3) . . ?
N3' C30' C31' 106.4(4) . . ?
N3' C30' C32' 107.9(4) . . ?
N3' C30' C33' 112.7(3) . . ?
C31' C30' C32' 108.1(4) . . ?
C31' C30' C33' 111.4(4) . . ?
C33' C30' C32' 110.2(4) . . ?
O4 C35 C34 108.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 I1 0.84 2.62 3.420(4) 159.8 . yes
O2 H2 I1' 0.84 2.62 3.464(2) 179.8 . yes
O3 H3 O4 0.84 1.97 2.764(4) 158.4 . yes
N4 H4 N1 1.00 2.14 2.869(4) 128.5 . yes
O1' H1' I1' 0.84 2.71 3.532(3) 166.5 . yes
O2' H2' I1' 0.84 2.59 3.421(4) 168.2 . yes
O1" H1" I1' 0.84 2.49 3.235(8) 149.1 . yes
O2" H2" I1' 0.84 2.73 3.561(6) 171.7 . yes
O3' H3' I1' 0.84 2.69 3.497(3) 162.8 . yes
N4' H4' O1' 1.00 2.02 2.750(4) 127.6 . yes
N4' H4' O2" 1.00 1.98 2.730(6) 129.9 . yes
N4' H4' O3' 1.00 2.14 2.829(4) 124.8 . yes
O4 H4a I1 0.84 2.65 3.485(3) 175.2 . yes
