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

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

data_mo_2016531_0m
_database_code_depnum_ccdc_archive 'CCDC 1584746'
loop_
_audit_author_name
_audit_author_address
'Meiqi Li' 'Shanghai Institute of Materia Medica, Chinese Academy of Sciences'
_audit_update_record             
;
2017-11-09 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-09-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5221)
;
_chemical_formula_moiety         'Cl, C21 H18 N O4, C H4 O'
_chemical_formula_sum            'C22 H22 Cl N O5'
_chemical_formula_weight         415.88
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.2953(4)
_cell_length_b                   8.1752(3)
_cell_length_c                   17.7914(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.999(2)
_cell_angle_gamma                90
_cell_volume                     1919.37(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4241
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0606 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.8987.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4391
_exptl_crystal_description       prism
_exptl_crystal_F_000             873.0521
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15856
_diffrn_reflns_theta_full        27.6106
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         1.54
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.9906
_diffrn_measured_fraction_theta_max 0.9906
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3321
_reflns_number_total             4434
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.4014
_refine_diff_density_min         -0.3202
_refine_diff_density_rms         0.0747
_refine_ls_d_res_high            0.7668
_refine_ls_d_res_low             13.1962
_refine_ls_goodness_of_fit_ref   0.9605
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      0.9605
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C16(H16), C20(H20), C14(H14), C8(H8), C21(H21)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C1(H1a,H1b,H1c), C22(H22a,H22b,H22c)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5a)
;
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_refinement_flags_posn
Cl1 Cl 1.34577(3) 0.01320(6) 0.69501(2) 0.02907(16) Uani 1.000000 .
O3 O 0.27016(9) 0.91155(17) 0.26105(7) 0.0275(3) Uani 1.000000 .
O1 O 0.13840(10) 1.07947(19) 0.33923(7) 0.0337(3) Uani 1.000000 .
O4 O 0.89353(10) 0.37336(19) 0.59512(8) 0.0359(4) Uani 1.000000 .
O2 O 0.88565(9) 0.40611(19) 0.46543(8) 0.0358(4) Uani 1.000000 .
N1 N 0.51851(10) 0.67878(18) 0.36952(8) 0.0200(3) Uani 1.000000 .
O5 O 1.13168(11) 0.1150(2) 0.61921(8) 0.0501(5) Uani 1.000000 .
H5a H 1.1879(11) 0.068(3) 0.6292(3) 0.0752(7) Uiso 1.000000 GR
C19 C 0.39351(12) 0.8543(2) 0.45651(10) 0.0204(4) Uani 1.000000 .
C18 C 0.48337(12) 0.7718(2) 0.49185(9) 0.0207(4) Uani 1.000000 .
C15 C 0.65319(13) 0.6061(2) 0.56593(10) 0.0228(4) Uani 1.000000 .
C4 C 0.37209(12) 0.8461(2) 0.37700(9) 0.0203(4) Uani 1.000000 .
C7 C 0.64189(12) 0.6140(2) 0.48482(9) 0.0204(4) Uani 1.000000 .
C5 C 0.43658(12) 0.7536(2) 0.33698(9) 0.0211(4) Uani 1.000000 .
H5 H 0.42053(12) 0.7443(2) 0.28365(9) 0.0253(4) Uiso 1.000000 R
C17 C 0.50443(13) 0.7719(2) 0.57238(10) 0.0236(4) Uani 1.000000 .
H17 H 0.46192(13) 0.8319(2) 0.60162(10) 0.0283(5) Uiso 1.000000 R
C3 C 0.28458(13) 0.9210(2) 0.33832(10) 0.0227(4) Uani 1.000000 .
C6 C 0.54943(12) 0.6889(2) 0.44830(9) 0.0196(4) Uani 1.000000 .
C2 C 0.21962(13) 1.0067(2) 0.37968(11) 0.0246(4) Uani 1.000000 .
C16 C 0.58384(13) 0.6879(2) 0.60757(10) 0.0250(4) Uani 1.000000 .
H16 H 0.59356(13) 0.6834(2) 0.66132(10) 0.0300(5) Uiso 1.000000 R
C20 C 0.32503(13) 0.9387(2) 0.49666(10) 0.0246(4) Uani 1.000000 .
H20 H 0.33681(13) 0.9441(2) 0.55035(10) 0.0295(5) Uiso 1.000000 R
C13 C 0.80598(13) 0.4545(2) 0.56843(11) 0.0266(4) Uani 1.000000 .
C9 C 0.80015(13) 0.4721(2) 0.49041(11) 0.0268(4) Uani 1.000000 .
C14 C 0.73644(13) 0.5236(2) 0.60812(10) 0.0263(4) Uani 1.000000 .
H14 H 0.74272(13) 0.5175(2) 0.66181(10) 0.0315(5) Uiso 1.000000 R
C8 C 0.72330(13) 0.5514(2) 0.44765(10) 0.0261(4) Uani 1.000000 .
H8 H 0.72373(13) 0.5647(2) 0.39464(10) 0.0313(5) Uiso 1.000000 R
C21 C 0.24114(14) 1.0137(2) 0.45884(11) 0.0266(4) Uani 1.000000 .
H21 H 0.19648(14) 1.0717(2) 0.48705(11) 0.0319(5) Uiso 1.000000 R
C12 C 0.57260(13) 0.5801(3) 0.31709(10) 0.0259(4) Uani 1.000000 .
H12a H 0.5276(3) 0.5604(13) 0.2701(3) 0.0389(6) Uiso 1.000000 GR
H12b H 0.6329(5) 0.6395(7) 0.3056(6) 0.0389(6) Uiso 1.000000 GR
H12c H 0.5930(9) 0.4753(7) 0.3409(3) 0.0389(6) Uiso 1.000000 GR
C11 C 0.17857(14) 0.8295(3) 0.22902(11) 0.0339(5) Uani 1.000000 .
H11a H 0.1871(4) 0.7890(15) 0.1783(3) 0.0508(7) Uiso 1.000000 GR
H11b H 0.1648(6) 0.7373(10) 0.2615(4) 0.0508(7) Uiso 1.000000 GR
H11c H 0.1217(2) 0.9065(5) 0.2255(7) 0.0508(7) Uiso 1.000000 GR
C1 C 0.06606(14) 1.1604(3) 0.37916(12) 0.0364(5) Uani 1.000000 .
H1a H 0.0158(7) 1.2155(15) 0.34293(13) 0.0546(8) Uiso 1.000000 GR
H1b H 0.0321(8) 1.0800(4) 0.4082(7) 0.0546(8) Uiso 1.000000 GR
H1c H 0.1006(2) 1.2414(13) 0.4138(6) 0.0546(8) Uiso 1.000000 GR
C10 C 0.93381(14) 0.3148(3) 0.52906(11) 0.0354(5) Uani 1.000000 .
H10a H 1.00810(14) 0.3313(3) 0.53427(11) 0.0425(6) Uiso 1.000000 R
H10b H 0.91960(14) 0.1966(3) 0.52196(11) 0.0425(6) Uiso 1.000000 R
C22 C 1.10164(18) 0.1803(4) 0.68596(15) 0.0625(8) Uani 1.000000 .
H22a H 1.0336(6) 0.227(2) 0.6751(3) 0.0937(12) Uiso 1.000000 GR
H22b H 1.1010(14) 0.0934(6) 0.7238(4) 0.0937(12) Uiso 1.000000 GR
H22c H 1.1494(9) 0.2659(16) 0.7055(6) 0.0937(12) Uiso 1.000000 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
O3 C3 1.367(2) . ?
O3 C11 1.445(2) . ?
O1 C2 1.359(2) . ?
O1 C1 1.426(2) . ?
O4 C13 1.373(2) . ?
O4 C10 1.432(2) . ?
O2 C9 1.380(2) . ?
O2 C10 1.439(2) . ?
N1 C5 1.320(2) . ?
N1 C6 1.414(2) . ?
N1 C12 1.484(2) . ?
O5 H5a 0.8400 . ?
O5 C22 1.404(3) . ?
C19 C18 1.447(2) . ?
C19 C4 1.410(2) . ?
C19 C20 1.405(2) . ?
C18 C17 1.426(2) . ?
C18 C6 1.413(2) . ?
C15 C7 1.434(2) . ?
C15 C16 1.418(3) . ?
C15 C14 1.429(2) . ?
C4 C5 1.401(2) . ?
C4 C3 1.417(2) . ?
C7 C6 1.454(2) . ?
C7 C8 1.430(2) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.348(3) . ?
C3 C2 1.390(2) . ?
C2 C21 1.404(3) . ?
C16 H16 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.374(3) . ?
C13 C9 1.388(3) . ?
C13 C14 1.353(3) . ?
C9 C8 1.361(3) . ?
C14 H14 0.9500 . ?
C8 H8 0.9500 . ?
C21 H21 0.9500 . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C1 H1a 0.9800 . ?
C1 H1b 0.9800 . ?
C1 H1c 0.9800 . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C3 115.54(13) . . ?
C1 O1 C2 118.67(15) . . ?
C10 O4 C13 105.29(15) . . ?
C10 O2 C9 104.75(14) . . ?
C6 N1 C5 122.14(14) . . ?
C12 N1 C5 114.44(14) . . ?
C12 N1 C6 123.39(14) . . ?
C22 O5 H5a 109.5 . . ?
C4 C19 C18 117.96(15) . . ?
C20 C19 C18 124.04(16) . . ?
C20 C19 C4 117.99(16) . . ?
C17 C18 C19 119.14(16) . . ?
C6 C18 C19 121.37(15) . . ?
C6 C18 C17 119.48(16) . . ?
C16 C15 C7 120.62(16) . . ?
C14 C15 C7 121.97(16) . . ?
C14 C15 C16 117.34(16) . . ?
C5 C4 C19 118.31(15) . . ?
C3 C4 C19 121.34(16) . . ?
C3 C4 C5 120.25(15) . . ?
C6 C7 C15 116.60(15) . . ?
C8 C7 C15 117.18(15) . . ?
C8 C7 C6 126.20(15) . . ?
C4 C5 N1 123.42(15) . . ?
H5 C5 N1 118.29(9) . . ?
H5 C5 C4 118.29(10) . . ?
H17 C17 C18 119.56(10) . . ?
C16 C17 C18 120.87(17) . . ?
C16 C17 H17 119.56(11) . . ?
C4 C3 O3 118.04(15) . . ?
C2 C3 O3 122.74(16) . . ?
C2 C3 C4 119.15(16) . . ?
C18 C6 N1 116.53(15) . . ?
C7 C6 N1 123.09(15) . . ?
C7 C6 C18 120.34(15) . . ?
C3 C2 O1 116.41(16) . . ?
C21 C2 O1 124.41(16) . . ?
C21 C2 C3 119.18(16) . . ?
C17 C16 C15 121.30(16) . . ?
H16 C16 C15 119.35(10) . . ?
H16 C16 C17 119.35(11) . . ?
H20 C20 C19 119.75(10) . . ?
C21 C20 C19 120.50(16) . . ?
C21 C20 H20 119.75(11) . . ?
C9 C13 O4 109.73(16) . . ?
C14 C13 O4 128.72(17) . . ?
C14 C13 C9 121.32(17) . . ?
C13 C9 O2 109.48(16) . . ?
C8 C9 O2 126.71(17) . . ?
C8 C9 C13 123.70(17) . . ?
C13 C14 C15 117.24(17) . . ?
H14 C14 C15 121.38(10) . . ?
H14 C14 C13 121.38(11) . . ?
C9 C8 C7 118.08(16) . . ?
H8 C8 C7 120.96(10) . . ?
H8 C8 C9 120.96(11) . . ?
C20 C21 C2 121.82(17) . . ?
H21 C21 C2 119.09(11) . . ?
H21 C21 C20 119.09(11) . . ?
H12a C12 N1 109.5 . . ?
H12b C12 N1 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 N1 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H11a C11 O3 109.5 . . ?
H11b C11 O3 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 O3 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
O2 C10 O4 107.29(16) . . ?
H10a C10 O4 110.26(10) . . ?
H10a C10 O2 110.26(9) . . ?
H10b C10 O4 110.26(11) . . ?
H10b C10 O2 110.26(11) . . ?
H10b C10 H10a 108.5 . . ?
H22a C22 O5 109.5 . . ?
H22b C22 O5 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 O5 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?

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

data_mo_2016577_0m
_database_code_depnum_ccdc_archive 'CCDC 1584747'
loop_
_audit_author_name
_audit_author_address
'Meiqi Li' 'Shanghai Institute of Materia Medica, Chinese Academy of Sciences'
_audit_update_record             
;
2017-11-09 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-10-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C21 H18 N O4'
_chemical_formula_sum            'C21 H18 Cl N O4'
_chemical_formula_weight         383.81
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.9199(9)
_cell_length_b                   7.3899(2)
_cell_length_c                   18.0028(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.427(2)
_cell_angle_gamma                90.00
_cell_volume                     3445.42(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7179
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9156.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28089
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         1.57
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3111
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0406
_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     
'calc w=1/[σ²(Fo²)+(0.0583P)²+2.5812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C14(H14), C16(H16), C17(H17), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.339800(16) -0.74703(6) 0.33200(3) 0.03024(14) Uani 1 d . . .
O1 O 0.42058(5) 0.23955(16) 0.66078(8) 0.0310(3) Uani 1 d . . .
O2 O 0.02009(4) 0.71540(19) 0.50404(8) 0.0353(3) Uani 1 d . . .
O4 O -0.01158(5) 0.79753(19) 0.36627(8) 0.0373(3) Uani 1 d . . .
O3 O 0.35655(4) 0.31150(17) 0.73528(7) 0.0271(3) Uani 1 d . . .
N1 N 0.22288(5) 0.58461(18) 0.61534(8) 0.0192(3) Uani 1 d . . .
C1 C 0.45578(7) 0.2320(3) 0.62499(14) 0.0362(5) Uani 1 d . . .
H1A H 0.4416 0.1536 0.5760 0.054 Uiso 1 calc . . GR
H1B H 0.4889 0.1831 0.6657 0.054 Uiso 1 calc . . GR
H1C H 0.4610 0.3540 0.6087 0.054 Uiso 1 calc . . GR
C2 C 0.37308(6) 0.3145(2) 0.61411(11) 0.0234(4) Uani 1 d . . .
C3 C 0.34320(6) 0.3530(2) 0.65458(10) 0.0210(3) Uani 1 d . . .
C4 C 0.29420(6) 0.4333(2) 0.60959(10) 0.0191(3) Uani 1 d . . .
C5 C 0.26838(6) 0.5051(2) 0.65285(10) 0.0201(3) Uani 1 d . . .
H5 H 0.2843 0.4962 0.7116 0.024 Uiso 1 calc . . R
C6 C 0.19533(6) 0.5886(2) 0.52800(9) 0.0188(3) Uani 1 d . . .
C7 C 0.14167(6) 0.6414(2) 0.48663(10) 0.0200(3) Uani 1 d . . .
C8 C 0.10812(6) 0.6451(2) 0.52568(10) 0.0238(4) Uani 1 d . . .
H8 H 0.1199 0.6091 0.5818 0.029 Uiso 1 calc . . R
C9 C 0.05892(6) 0.7019(2) 0.47966(11) 0.0254(4) Uani 1 d . . .
C10 C -0.02548(8) 0.7563(3) 0.43128(14) 0.0509(6) Uani 1 d . . .
H10A H -0.0432 0.8611 0.4414 0.061 Uiso 1 calc . . R
H10B H -0.0493 0.6514 0.4153 0.061 Uiso 1 calc . . R
C15 C 0.12053(6) 0.6800(2) 0.40000(10) 0.0224(4) Uani 1 d . . .
C14 C 0.06848(7) 0.7390(2) 0.35452(11) 0.0264(4) Uani 1 d . . .
H14 H 0.0548 0.7693 0.2974 0.032 Uiso 1 calc . . R
C13 C 0.03936(6) 0.7502(2) 0.39599(11) 0.0258(4) Uani 1 d . . .
C16 C 0.15044(6) 0.6483(2) 0.35661(10) 0.0253(4) Uani 1 d . . .
H16 H 0.1367 0.6791 0.2995 0.030 Uiso 1 calc . . R
C17 C 0.19824(6) 0.5747(2) 0.39536(10) 0.0229(4) Uani 1 d . . .
H17 H 0.2160 0.5440 0.3637 0.027 Uiso 1 calc . . R
C18 C 0.22248(6) 0.5421(2) 0.48241(10) 0.0198(3) Uani 1 d . . .
C12 C 0.20687(6) 0.6879(2) 0.67123(10) 0.0251(4) Uani 1 d . . .
H12A H 0.1859 0.6100 0.6883 0.038 Uiso 1 calc . . GR
H12B H 0.1866 0.7937 0.6417 0.038 Uiso 1 calc . . GR
H12C H 0.2376 0.7277 0.7204 0.038 Uiso 1 calc . . GR
C19 C 0.27353(6) 0.4654(2) 0.52331(10) 0.0197(3) Uani 1 d . . .
C20 C 0.30413(6) 0.4184(2) 0.48403(11) 0.0240(4) Uani 1 d . . .
H20 H 0.2912 0.4358 0.4259 0.029 Uiso 1 calc . . R
C21 C 0.35267(6) 0.3473(2) 0.52862(11) 0.0255(4) Uani 1 d . . .
H21 H 0.3730 0.3194 0.5007 0.031 Uiso 1 calc . . R
C11 C 0.40597(7) 0.3673(3) 0.79729(12) 0.0449(6) Uani 1 d . . .
H11A H 0.4292 0.2627 0.8156 0.067 Uiso 1 calc . . GR
H11B H 0.4023 0.4182 0.8447 0.067 Uiso 1 calc . . GR
H11C H 0.4203 0.4592 0.7741 0.067 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.428(2) . ?
O1 C2 1.368(2) . ?
O2 C9 1.379(2) . ?
O2 C10 1.417(2) . ?
O4 C10 1.429(3) . ?
O4 C13 1.370(2) . ?
O3 C3 1.362(2) . ?
O3 C11 1.428(2) . ?
N1 C5 1.3198(19) . ?
N1 C6 1.4117(19) . ?
N1 C12 1.491(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.385(2) . ?
C2 C21 1.402(2) . ?
C3 C4 1.412(2) . ?
C4 C5 1.401(2) . ?
C4 C19 1.414(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(2) . ?
C6 C18 1.408(2) . ?
C7 C8 1.430(2) . ?
C7 C15 1.428(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.356(2) . ?
C9 C13 1.399(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 C14 1.425(2) . ?
C15 C16 1.420(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.354(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.355(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.424(2) . ?
C18 C19 1.440(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C19 C20 1.401(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(2) . ?
C21 H21 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.47(15) . . ?
C9 O2 C10 105.97(15) . . ?
C13 O4 C10 105.73(14) . . ?
C3 O3 C11 118.61(14) . . ?
C5 N1 C6 121.27(14) . . ?
C5 N1 C12 114.89(13) . . ?
C6 N1 C12 123.38(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.80(15) . . ?
O1 C2 C21 124.12(15) . . ?
C3 C2 C21 119.03(15) . . ?
O3 C3 C2 124.61(15) . . ?
O3 C3 C4 116.23(14) . . ?
C2 C3 C4 119.09(15) . . ?
C3 C4 C19 121.74(15) . . ?
C5 C4 C3 119.17(14) . . ?
C5 C4 C19 118.54(14) . . ?
N1 C5 C4 122.74(15) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N1 C6 C7 121.62(14) . . ?
C18 C6 N1 117.36(13) . . ?
C18 C6 C7 121.02(14) . . ?
C8 C7 C6 124.06(14) . . ?
C15 C7 C6 117.17(15) . . ?
C15 C7 C8 118.62(14) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.57(15) . . ?
C9 C8 H8 121.2 . . ?
O2 C9 C13 109.15(14) . . ?
C8 C9 O2 127.56(16) . . ?
C8 C9 C13 123.25(17) . . ?
O2 C10 O4 108.52(16) . . ?
O2 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
O4 C10 H10A 110.0 . . ?
O4 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C14 C15 C7 121.21(16) . . ?
C16 C15 C7 119.90(15) . . ?
C16 C15 C14 118.76(15) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 C15 117.34(16) . . ?
C13 C14 H14 121.3 . . ?
O4 C13 C9 109.55(16) . . ?
C14 C13 O4 128.67(16) . . ?
C14 C13 C9 121.70(16) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.99(15) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.64(16) . . ?
C18 C17 H17 119.2 . . ?
C6 C18 C17 118.11(14) . . ?
C6 C18 C19 120.57(14) . . ?
C17 C18 C19 121.32(15) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C19 C18 117.62(14) . . ?
C20 C19 C4 117.37(15) . . ?
C20 C19 C18 125.00(15) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.71(16) . . ?
C21 C20 H20 119.6 . . ?
C2 C21 H21 119.0 . . ?
C20 C21 C2 121.93(16) . . ?
C20 C21 H21 119.0 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O3 -4.1(2) . . . . ?
O1 C2 C3 C4 178.93(13) . . . . ?
O1 C2 C21 C20 178.19(15) . . . . ?
O2 C9 C13 O4 0.9(2) . . . . ?
O2 C9 C13 C14 -176.12(15) . . . . ?
O3 C3 C4 C5 15.4(2) . . . . ?
O3 C3 C4 C19 -173.25(14) . . . . ?
N1 C6 C7 C8 -18.0(2) . . . . ?
N1 C6 C7 C15 166.40(14) . . . . ?
N1 C6 C18 C17 -169.48(13) . . . . ?
N1 C6 C18 C19 9.9(2) . . . . ?
C1 O1 C2 C3 -167.94(15) . . . . ?
C1 O1 C2 C21 14.6(2) . . . . ?
C2 C3 C4 C5 -167.39(15) . . . . ?
C2 C3 C4 C19 3.9(2) . . . . ?
C3 C2 C21 C20 0.8(2) . . . . ?
C3 C4 C5 N1 178.99(14) . . . . ?
C3 C4 C19 C18 177.84(14) . . . . ?
C3 C4 C19 C20 -1.6(2) . . . . ?
C4 C19 C20 C21 -1.2(2) . . . . ?
C5 N1 C6 C7 167.18(14) . . . . ?
C5 N1 C6 C18 -13.9(2) . . . . ?
C5 C4 C19 C18 -10.8(2) . . . . ?
C5 C4 C19 C20 169.83(14) . . . . ?
C6 N1 C5 C4 5.4(2) . . . . ?
C6 C7 C8 C9 178.43(15) . . . . ?
C6 C7 C15 C14 -177.87(14) . . . . ?
C6 C7 C15 C16 6.3(2) . . . . ?
C6 C18 C19 C4 2.1(2) . . . . ?
C6 C18 C19 C20 -178.51(15) . . . . ?
C7 C6 C18 C17 9.4(2) . . . . ?
C7 C6 C18 C19 -171.19(14) . . . . ?
C7 C8 C9 O2 179.59(16) . . . . ?
C7 C8 C9 C13 2.3(3) . . . . ?
C7 C15 C14 C13 -2.5(2) . . . . ?
C7 C15 C16 C17 2.7(2) . . . . ?
C8 C7 C15 C14 6.3(2) . . . . ?
C8 C7 C15 C16 -169.51(14) . . . . ?
C8 C9 C13 O4 178.65(16) . . . . ?
C8 C9 C13 C14 1.6(3) . . . . ?
C9 O2 C10 O4 -9.9(2) . . . . ?
C10 O2 C9 C8 -172.02(19) . . . . ?
C10 O2 C9 C13 5.6(2) . . . . ?
C10 O4 C13 C9 -6.9(2) . . . . ?
C10 O4 C13 C14 169.8(2) . . . . ?
C15 C7 C8 C9 -6.0(2) . . . . ?
C15 C14 C13 O4 -177.91(16) . . . . ?
C15 C14 C13 C9 -1.5(2) . . . . ?
C15 C16 C17 C18 -6.1(2) . . . . ?
C14 C15 C16 C17 -173.20(15) . . . . ?
C13 O4 C10 O2 10.4(2) . . . . ?
C16 C15 C14 C13 173.36(15) . . . . ?
C16 C17 C18 C6 0.0(2) . . . . ?
C16 C17 C18 C19 -179.38(15) . . . . ?
C17 C18 C19 C4 -178.47(14) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C18 C6 C7 C8 163.16(15) . . . . ?
C18 C6 C7 C15 -12.4(2) . . . . ?
C18 C19 C20 C21 179.44(15) . . . . ?
C12 N1 C5 C4 -167.01(15) . . . . ?
C12 N1 C6 C7 -21.1(2) . . . . ?
C12 N1 C6 C18 157.80(15) . . . . ?
C19 C4 C5 N1 7.4(2) . . . . ?
C19 C20 C21 C2 1.6(2) . . . . ?
C21 C2 C3 O3 173.45(14) . . . . ?
C21 C2 C3 C4 -3.5(2) . . . . ?
C11 O3 C3 C2 52.2(2) . . . . ?
C11 O3 C3 C4 -130.83(17) . . . . ?

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

data_mo_2016601_0m
_database_code_depnum_ccdc_archive 'CCDC 1584748'
loop_
_audit_author_name
_audit_author_address
'Meiqi Li' 'Shanghai Institute of Materia Medica, Chinese Academy of Sciences'
_audit_update_record             
;
2017-11-09 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;
_audit_creation_date             2016-10-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C21 H18 N O4, 4.5(H2 O)'
_chemical_formula_sum            'C21 H27 Cl N O8.50'
_chemical_formula_weight         464.88
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8891(2)
_cell_length_b                   20.9101(7)
_cell_length_c                   30.2189(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4353.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6537
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      22.32
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.7992.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1960
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            75657
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.184
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7170
_reflns_number_total             10017
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.38(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         10017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.007
_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)+(0.0433P)²+0.6463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.62(8) 0.38(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3.a Free rotating group:
 O9(H9C,H9D), O12(H12D,H12E), O15(H15A,H15B), O17(H17A,H17B), O16(H16A,H16B),
 O11(H11D,H11E), O13(H13A,H13B), O10(H10D,H10E), O14(H14A,H14B)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C41(H41), C16(H16), C38(H38), C20(H20), C28(H28), C7(H7), C14(H14),
 C35(H35), C42(H42), C25(H25), C4(H4), C17(H17), C21(H21)
3.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C12(H12A,H12B,H12C), C31(H31A,H31B,H31C), C11(H11A,H11B,
 H11C), C10(H10A,H10B,H10C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl -0.45333(15) 0.46440(5) 0.45932(3) 0.0405(3) Uani 1 1 d . . . . .
Cl02 Cl 0.24429(17) 0.49900(5) 0.78056(4) 0.0510(3) Uani 1 1 d . . . . .
O3 O 0.5214(4) 0.62680(10) 0.59516(7) 0.0269(6) Uani 1 1 d . . . . .
O7 O 0.9559(4) 0.36581(10) 0.58663(7) 0.0261(5) Uani 1 1 d . . . . .
O5 O 1.0191(4) 0.26054(11) 0.53686(7) 0.0313(6) Uani 1 1 d . . . . .
O2 O 0.4363(4) 0.58995(11) 0.89538(8) 0.0324(6) Uani 1 1 d . . . . .
O1 O 0.4774(4) 0.73516(11) 0.54417(8) 0.0336(6) Uani 1 1 d . . . . .
O4 O 0.4756(4) 0.68425(11) 0.93435(8) 0.0326(6) Uani 1 1 d . . . . .
O6 O 1.0699(4) 0.39518(11) 0.89002(8) 0.0341(6) Uani 1 1 d . . . . .
O8 O 1.0235(4) 0.30021(11) 0.92773(8) 0.0349(6) Uani 1 1 d . . . . .
N2 N 0.8854(4) 0.35429(12) 0.72107(9) 0.0181(6) Uani 1 1 d . . . . .
N1 N 0.6149(4) 0.63609(12) 0.72728(9) 0.0184(6) Uani 1 1 d . . . . .
O9 O 0.6124(4) 0.47289(16) 0.64007(9) 0.0428(7) Uani 1 1 d . . . . .
H9C H 0.5951 0.4576 0.6143 0.064 Uiso 1 1 d G . . . .
H9D H 0.5031 0.4781 0.6526 0.064 Uiso 1 1 d G . . . .
O12 O -0.0422(4) 0.53780(16) 0.64832(9) 0.0476(7) Uani 1 1 d . . . . .
H12D H 0.0097 0.5515 0.6246 0.071 Uiso 1 1 d G . . . .
H12E H -0.1504 0.5203 0.6423 0.071 Uiso 1 1 d G . . . .
O15 O -0.0988(4) 0.55312(13) 0.43552(10) 0.0458(8) Uani 1 1 d . . . . .
H15A H -0.1894 0.5274 0.4448 0.069 Uiso 1 1 d G . . . .
H15B H -0.0867 0.5493 0.4070 0.069 Uiso 1 1 d G . . . .
O17 O -0.4175(4) 0.46709(14) 0.35023(10) 0.0460(7) Uani 1 1 d . . . . .
H17A H -0.4334 0.4751 0.3776 0.069 Uiso 1 1 d G . . . .
H17B H -0.5169 0.4793 0.3359 0.069 Uiso 1 1 d G . . . .
O16 O -0.0937(5) 0.54536(12) 0.34311(11) 0.0486(8) Uani 1 1 d . . . . .
H16A H 0.0021 0.5294 0.3293 0.073 Uiso 1 1 d G . . . .
H16B H -0.1877 0.5191 0.3429 0.073 Uiso 1 1 d G . . . .
O11 O 0.5991(4) 0.41650(17) 0.55807(10) 0.0512(8) Uani 1 1 d . . . . .
H11D H 0.7111 0.3999 0.5609 0.077 Uiso 1 1 d G . . . .
H11E H 0.5875 0.4321 0.5322 0.077 Uiso 1 1 d G . . . .
O13 O 0.1321(4) 0.59077(18) 0.57563(12) 0.0558(9) Uani 1 1 d . . . . .
H13A H 0.2484 0.5994 0.5829 0.084 Uiso 1 1 d G . . . .
H13B H 0.1318 0.5697 0.5515 0.084 Uiso 1 1 d G . . . .
C5 C 0.5848(4) 0.69234(15) 0.75208(11) 0.0173(7) Uani 1 1 d . . . . .
C18 C 0.5792(4) 0.75051(14) 0.72879(10) 0.0178(7) Uani 1 1 d . . . . .
C26 C 0.9163(4) 0.29708(15) 0.74517(11) 0.0189(7) Uani 1 1 d . . . . .
C27 C 0.9430(5) 0.29816(15) 0.79230(10) 0.0186(7) Uani 1 1 d . . . . .
C15 C 0.5667(4) 0.74961(15) 0.82267(11) 0.0199(7) Uani 1 1 d . . . . .
C39 C 0.9209(4) 0.23961(15) 0.72092(11) 0.0183(7) Uani 1 1 d . . . . .
O10 O 0.2607(5) 0.46607(17) 0.68100(10) 0.0601(9) Uani 1 1 d . . . . .
H10D H 0.2712 0.4729 0.7093 0.090 Uiso 1 1 d G . . . .
H10E H 0.2095 0.4994 0.6684 0.090 Uiso 1 1 d G . . . .
C2 C 0.5350(5) 0.68721(14) 0.61268(10) 0.0199(7) Uani 1 1 d . . . . .
O14 O 0.1672(5) 0.5272(2) 0.49886(10) 0.0654(10) Uani 1 1 d . . . . .
H14A H 0.2765 0.5125 0.4886 0.098 Uiso 1 1 d G . . . .
H14B H 0.0902 0.5362 0.4769 0.098 Uiso 1 1 d G . . . .
C37 C 0.9077(4) 0.18096(15) 0.79008(11) 0.0216(8) Uani 1 1 d . . . . .
H37 H 0.8891 0.1417 0.8053 0.026 Uiso 1 1 calc R . . . .
C36 C 0.9318(5) 0.23834(15) 0.81500(11) 0.0200(7) Uani 1 1 d . . . . .
C41 C 0.9655(5) 0.18631(15) 0.64698(11) 0.0216(7) Uani 1 1 d . . . . .
H41 H 0.9644 0.1451 0.6602 0.026 Uiso 1 1 calc R . . . .
C6 C 0.5572(4) 0.69023(14) 0.79930(10) 0.0180(7) Uani 1 1 d . . . . .
C16 C 0.5896(4) 0.80750(15) 0.79838(11) 0.0217(7) Uani 1 1 d . . . . .
H16 H 0.6061 0.8465 0.8141 0.026 Uiso 1 1 calc R . . . .
C40 C 0.9394(5) 0.24078(14) 0.67361(11) 0.0180(7) Uani 1 1 d . . . . .
C38 C 0.9106(4) 0.18118(15) 0.74525(11) 0.0201(7) Uani 1 1 d . . . . .
H38 H 0.9058 0.1417 0.7297 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4880(5) 0.63774(15) 0.86704(11) 0.0220(7) Uani 1 1 d . . . . .
C24 C 0.9392(5) 0.30109(14) 0.65217(11) 0.0190(7) Uani 1 1 d . . . . .
C20 C 0.5389(5) 0.80607(15) 0.65523(11) 0.0237(7) Uani 1 1 d . . . . .
H20 H 0.5416 0.8470 0.6689 0.028 Uiso 1 1 calc R . . . .
C23 C 0.9651(5) 0.30604(15) 0.60615(11) 0.0216(7) Uani 1 1 d . . . . .
C28 C 0.9946(5) 0.35412(15) 0.81660(10) 0.0216(7) Uani 1 1 d . . . . .
H28 H 1.0148 0.3939 0.8022 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5070(5) 0.63352(15) 0.82253(10) 0.0210(7) Uani 1 1 d . . . . .
H7 H 0.4876 0.5942 0.8074 0.025 Uiso 1 1 calc R . . . .
C3 C 0.5603(5) 0.69102(15) 0.65905(11) 0.0202(7) Uani 1 1 d . . . . .
C14 C 0.5430(5) 0.75127(15) 0.86936(11) 0.0229(7) Uani 1 1 d . . . . .
H14 H 0.5510 0.7904 0.8853 0.027 Uiso 1 1 calc R . . . .
C19 C 0.5625(5) 0.75086(15) 0.68107(10) 0.0191(7) Uani 1 1 d . . . . .
C35 C 0.9529(5) 0.23544(15) 0.86162(11) 0.0232(7) Uani 1 1 d . . . . .
H35 H 0.9416 0.1960 0.8771 0.028 Uiso 1 1 calc R . . . .
C13 C 0.5087(5) 0.69493(15) 0.89044(11) 0.0223(7) Uani 1 1 d . . . . .
C42 C 0.9924(5) 0.19198(15) 0.60218(11) 0.0223(7) Uani 1 1 d . . . . .
H42 H 1.0107 0.1544 0.5850 0.027 Uiso 1 1 calc R . . . .
C25 C 0.8997(5) 0.35571(15) 0.67741(11) 0.0199(7) Uani 1 1 d . . . . .
H25 H 0.8826 0.3954 0.6626 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5985(5) 0.63578(15) 0.68364(11) 0.0199(7) Uani 1 1 d . . . . .
H4 H 0.6132 0.5964 0.6684 0.024 Uiso 1 1 calc R . . . .
C34 C 0.9898(5) 0.29080(16) 0.88340(11) 0.0249(8) Uani 1 1 d . . . . .
C29 C 1.0138(5) 0.34836(15) 0.86079(11) 0.0240(8) Uani 1 1 d . . . . .
C17 C 0.5887(4) 0.80862(15) 0.75366(11) 0.0206(7) Uani 1 1 d . . . . .
H17 H 0.5944 0.8484 0.7386 0.025 Uiso 1 1 calc R . . . .
C22 C 0.9938(5) 0.25189(15) 0.58087(10) 0.0228(7) Uani 1 1 d . . . . .
C1 C 0.5094(5) 0.74250(16) 0.58824(11) 0.0246(8) Uani 1 1 d . . . . .
C33 C 0.8069(5) 0.41354(15) 0.74144(12) 0.0229(8) Uani 1 1 d . . . . .
H33A H 0.7381 0.4027 0.7688 0.034 Uiso 1 1 calc GR . . . .
H33B H 0.7169 0.4342 0.7208 0.034 Uiso 1 1 calc GR . . . .
H33C H 0.9140 0.4428 0.7482 0.034 Uiso 1 1 calc GR . . . .
C21 C 0.5120(5) 0.80145(16) 0.61042(11) 0.0261(8) Uani 1 1 d . . . . .
H21 H 0.4945 0.8395 0.5938 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6979(5) 0.57670(15) 0.74664(12) 0.0234(8) Uani 1 1 d . . . . .
H12A H 0.7653 0.5870 0.7743 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.7899 0.5577 0.7257 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.5931 0.5462 0.7527 0.035 Uiso 1 1 calc GR . . . .
C9 C 0.4526(6) 0.61572(16) 0.93913(11) 0.0317(9) Uani 1 1 d . . . . .
H9A H 0.5663 0.5972 0.9545 0.038 Uiso 1 1 calc R . . . .
H9B H 0.3346 0.6059 0.9565 0.038 Uiso 1 1 calc R . . . .
C31 C 1.0483(7) 0.20502(16) 0.51004(11) 0.0338(9) Uani 1 1 d . . . . .
H31A H 1.0653 0.2180 0.4791 0.051 Uiso 1 1 calc GR . . . .
H31B H 0.9352 0.1768 0.5125 0.051 Uiso 1 1 calc GR . . . .
H31C H 1.1645 0.1822 0.5201 0.051 Uiso 1 1 calc GR . . . .
C11 C 0.6510(6) 0.61074(18) 0.55908(13) 0.0367(10) Uani 1 1 d . . . . .
H11A H 0.6049 0.6310 0.5318 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.6538 0.5642 0.5551 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.7820 0.6261 0.5659 0.055 Uiso 1 1 calc GR . . . .
C30 C 1.0454(7) 0.36833(17) 0.93315(12) 0.0383(10) Uani 1 1 d . . . . .
H30A H 0.9290 0.3866 0.9476 0.046 Uiso 1 1 calc R . . . .
H30B H 1.1600 0.3778 0.9518 0.046 Uiso 1 1 calc R . . . .
C10 C 0.4565(8) 0.79148(17) 0.51781(12) 0.0435(11) Uani 1 1 d . . . . .
H10A H 0.4293 0.7793 0.4871 0.065 Uiso 1 1 calc GR . . . .
H10B H 0.5769 0.8164 0.5190 0.065 Uiso 1 1 calc GR . . . .
H10C H 0.3491 0.8173 0.5293 0.065 Uiso 1 1 calc GR . . . .
C32 C 1.1428(6) 0.39202(18) 0.57422(14) 0.0393(10) Uani 1 1 d . . . . .
H32A H 1.2094 0.3622 0.5544 0.059 Uiso 1 1 calc GR . . . .
H32B H 1.2216 0.3986 0.6008 0.059 Uiso 1 1 calc GR . . . .
H32C H 1.1239 0.4330 0.5591 0.059 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.373(4) . ?
O3 C11 1.449(4) . ?
O7 C23 1.384(4) . ?
O7 C32 1.449(4) . ?
O5 C22 1.353(4) . ?
O5 C31 1.430(4) . ?
O2 C8 1.363(4) . ?
O2 C9 1.432(4) . ?
O1 C1 1.358(4) . ?
O1 C10 1.429(4) . ?
O4 C13 1.365(4) . ?
O4 C9 1.449(4) . ?
O6 C29 1.374(4) . ?
O6 C30 1.429(4) . ?
O8 C34 1.374(4) . ?
O8 C30 1.442(4) . ?
N2 C26 1.417(4) . ?
N2 C25 1.323(4) . ?
N2 C33 1.485(4) . ?
N1 C5 1.410(4) . ?
N1 C4 1.324(4) . ?
N1 C12 1.487(4) . ?
O9 H9C 0.8498 . ?
O9 H9D 0.8500 . ?
O12 H12D 0.8503 . ?
O12 H12E 0.8504 . ?
O15 H15A 0.8700 . ?
O15 H15B 0.8698 . ?
O17 H17A 0.8498 . ?
O17 H17B 0.8504 . ?
O16 H16A 0.8496 . ?
O16 H16B 0.8498 . ?
O11 H11D 0.8500 . ?
O11 H11E 0.8502 . ?
O13 H13A 0.8503 . ?
O13 H13B 0.8506 . ?
C5 C18 1.406(4) . ?
C5 C6 1.440(4) . ?
C18 C19 1.447(4) . ?
C18 C17 1.430(4) . ?
C26 C27 1.436(4) . ?
C26 C39 1.408(4) . ?
C27 C36 1.429(4) . ?
C27 C28 1.427(4) . ?
C15 C6 1.430(4) . ?
C15 C16 1.425(5) . ?
C15 C14 1.421(4) . ?
C39 C40 1.435(4) . ?
C39 C38 1.428(4) . ?
O10 H10D 0.8701 . ?
O10 H10E 0.8702 . ?
C2 C3 1.414(4) . ?
C2 C1 1.383(4) . ?
O14 H14A 0.8701 . ?
O14 H14B 0.8700 . ?
C37 H37 0.9500 . ?
C37 C36 1.426(4) . ?
C37 C38 1.355(5) . ?
C36 C35 1.417(4) . ?
C41 H41 0.9500 . ?
C41 C40 1.406(4) . ?
C41 C42 1.372(5) . ?
C6 C7 1.421(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.352(5) . ?
C40 C24 1.418(4) . ?
C38 H38 0.9500 . ?
C8 C7 1.354(4) . ?
C8 C13 1.397(4) . ?
C24 C23 1.406(4) . ?
C24 C25 1.400(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.403(4) . ?
C20 C21 1.370(5) . ?
C23 C22 1.380(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.347(4) . ?
C7 H7 0.9500 . ?
C3 C19 1.417(4) . ?
C3 C4 1.398(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.360(5) . ?
C35 H35 0.9500 . ?
C35 C34 1.356(5) . ?
C42 H42 0.9500 . ?
C42 C22 1.408(4) . ?
C25 H25 0.9500 . ?
C4 H4 0.9500 . ?
C34 C29 1.394(5) . ?
C17 H17 0.9500 . ?
C1 C21 1.403(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C21 H21 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 C11 117.5(3) . . ?
C23 O7 C32 114.3(3) . . ?
C22 O5 C31 117.8(3) . . ?
C8 O2 C9 106.5(3) . . ?
C1 O1 C10 118.0(3) . . ?
C13 O4 C9 106.1(2) . . ?
C29 O6 C30 105.9(3) . . ?
C34 O8 C30 105.7(3) . . ?
C26 N2 C33 123.1(3) . . ?
C25 N2 C26 121.4(3) . . ?
C25 N2 C33 114.9(3) . . ?
C5 N1 C12 123.0(3) . . ?
C4 N1 C5 121.4(3) . . ?
C4 N1 C12 114.9(3) . . ?
H9C O9 H9D 109.5 . . ?
H12D O12 H12E 109.4 . . ?
H15A O15 H15B 109.5 . . ?
H17A O17 H17B 109.5 . . ?
H16A O16 H16B 109.5 . . ?
H11D O11 H11E 109.5 . . ?
H13A O13 H13B 109.5 . . ?
N1 C5 C6 121.4(3) . . ?
C18 C5 N1 117.4(3) . . ?
C18 C5 C6 121.3(3) . . ?
C5 C18 C19 120.4(3) . . ?
C5 C18 C17 118.1(3) . . ?
C17 C18 C19 121.6(3) . . ?
N2 C26 C27 121.1(3) . . ?
C39 C26 N2 117.2(3) . . ?
C39 C26 C27 121.8(3) . . ?
C36 C27 C26 117.1(3) . . ?
C28 C27 C26 123.7(3) . . ?
C28 C27 C36 119.0(3) . . ?
C16 C15 C6 119.2(3) . . ?
C14 C15 C6 120.4(3) . . ?
C14 C15 C16 120.2(3) . . ?
C26 C39 C40 120.4(3) . . ?
C26 C39 C38 117.5(3) . . ?
C38 C39 C40 122.1(3) . . ?
H10D O10 H10E 109.5 . . ?
O3 C2 C3 116.3(3) . . ?
O3 C2 C1 123.7(3) . . ?
C1 C2 C3 119.9(3) . . ?
H14A O14 H14B 109.4 . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C38 C37 C36 121.6(3) . . ?
C37 C36 C27 119.3(3) . . ?
C35 C36 C27 120.6(3) . . ?
C35 C36 C37 120.1(3) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C42 C41 C40 120.8(3) . . ?
C15 C6 C5 117.2(3) . . ?
C7 C6 C5 123.2(3) . . ?
C7 C6 C15 119.5(3) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 H16 119.0 . . ?
C41 C40 C39 124.6(3) . . ?
C41 C40 C24 117.3(3) . . ?
C24 C40 C39 118.0(3) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 C39 121.2(3) . . ?
C37 C38 H38 119.4 . . ?
O2 C8 C13 109.6(3) . . ?
C7 C8 O2 127.0(3) . . ?
C7 C8 C13 123.3(3) . . ?
C23 C24 C40 121.2(3) . . ?
C25 C24 C40 118.5(3) . . ?
C25 C24 C23 120.2(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.5(3) . . ?
O7 C23 C24 118.8(3) . . ?
C22 C23 O7 120.8(3) . . ?
C22 C23 C24 120.4(3) . . ?
C27 C28 H28 121.3 . . ?
C29 C28 C27 117.5(3) . . ?
C29 C28 H28 121.3 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.4(3) . . ?
C8 C7 H7 121.3 . . ?
C2 C3 C19 121.1(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 C19 118.5(3) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 H14 121.2 . . ?
C20 C19 C18 124.6(3) . . ?
C20 C19 C3 117.6(3) . . ?
C3 C19 C18 117.7(3) . . ?
C36 C35 H35 121.1 . . ?
C34 C35 C36 117.7(3) . . ?
C34 C35 H35 121.1 . . ?
O4 C13 C8 109.6(3) . . ?
C14 C13 O4 128.8(3) . . ?
C14 C13 C8 121.5(3) . . ?
C41 C42 H42 119.0 . . ?
C41 C42 C22 121.9(3) . . ?
C22 C42 H42 119.0 . . ?
N2 C25 C24 122.6(3) . . ?
N2 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
N1 C4 C3 122.8(3) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
O8 C34 C29 109.5(3) . . ?
C35 C34 O8 128.9(3) . . ?
C35 C34 C29 121.4(3) . . ?
O6 C29 C34 109.5(3) . . ?
C28 C29 O6 126.9(3) . . ?
C28 C29 C34 123.5(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
O5 C22 C23 116.9(3) . . ?
O5 C22 C42 124.7(3) . . ?
C23 C22 C42 118.4(3) . . ?
O1 C1 C2 116.7(3) . . ?
O1 C1 C21 124.7(3) . . ?
C2 C1 C21 118.5(3) . . ?
N2 C33 H33A 109.5 . . ?
N2 C33 H33B 109.5 . . ?
N2 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C20 C21 C1 122.4(3) . . ?
C20 C21 H21 118.8 . . ?
C1 C21 H21 118.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C9 O4 106.8(3) . . ?
O2 C9 H9A 110.4 . . ?
O2 C9 H9B 110.4 . . ?
O4 C9 H9A 110.4 . . ?
O4 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O5 C31 H31A 109.5 . . ?
O5 C31 H31B 109.5 . . ?
O5 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C30 O8 107.3(3) . . ?
O6 C30 H30A 110.3 . . ?
O6 C30 H30B 110.3 . . ?
O8 C30 H30A 110.3 . . ?
O8 C30 H30B 110.3 . . ?
H30A C30 H30B 108.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C32 H32A 109.5 . . ?
O7 C32 H32B 109.5 . . ?
O7 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.62(8)
2 0.38(8)

