# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a20190174_acn1309
_database_code_depnum_ccdc_archive 'CCDC 1939205'
loop_
_audit_author_name
_audit_author_address
'Arkaitz Correa'
;Universidad del Pais Vasco
Spain
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2019-05-14T18:56:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C36 H36 N2 O11'
_chemical_formula_sum            'C36 H36 N2 O11'
_chemical_formula_weight         672.67
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   10.02984(8)
_cell_length_b                   10.88201(8)
_cell_length_c                   30.5021(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3329.14(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    22656
_cell_measurement_theta_min      3.997
_cell_measurement_theta_max      74.488

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.195
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 3 8 0.1264
-1 3 17 0.1353
4 2 15 0.1745
6 0 7 0.1855
1 -3 -17 0.1113
-6 1 -3 0.1338
-1 -5 13 0.0942
-1 3 5 0.1014
0 7 -6 0.1113
2 3 -17 0.1469
1 -7 -1 0.0764


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_T_max  0.881

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0018545
_diffrn_orient_matrix_ub_12      -0.1188924
_diffrn_orient_matrix_ub_13      0.027417
_diffrn_orient_matrix_ub_21      0.142541
_diffrn_orient_matrix_ub_22      0.0299931
_diffrn_orient_matrix_ub_23      0.0154929
_diffrn_orient_matrix_ub_31      -0.0571321
_diffrn_orient_matrix_ub_32      0.0707977
_diffrn_orient_matrix_ub_33      0.0394877
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_number            37271
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.314
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.764
_reflns_number_total             6308
_reflns_number_gt                6051
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00  21.00   1.00    1.00    --  -42.38   0.00  60.00  120
  2  ω     29.00  91.00   1.00    1.00    --   42.38-125.00   0.00   62
  3  ω     55.00  96.00   1.00    1.00    --  107.93-125.00-180.00   41
  4  ω     82.00 158.00   1.00    1.00    --  107.93  30.00 120.00   76
  5  ω     44.00  77.00   1.00    1.00    --  107.93 -45.00 -60.00   33
  6  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00  90.00   37
  7  ω     94.00 149.00   1.00    1.00    --  107.93  45.00  60.00   55
  8  ω     40.00  65.00   1.00    1.00    --  107.93 -30.00-180.00   25
  9  ω     34.00  62.00   1.00    1.00    --  107.93 -30.00 -90.00   28
 10  ω     74.00 158.00   1.00    1.00    --  107.93 125.00 150.00   84
 11  ω     41.00  67.00   1.00    1.00    --  107.93 -61.00 150.00   26
 12  ω    102.00 127.00   1.00    1.00    --  107.93 -61.00 150.00   25
 13  ω     41.00  66.00   1.00    1.00    --  107.93 -45.00   0.00   25
 14  ω    -51.00 -14.00   1.00    1.00    --  -42.38 125.00-180.00   37
 15  ω   -114.00 -36.00   1.00    1.00    --  -42.38 -38.00  30.00   78
 16  ω     31.00  75.00   1.00    1.00    --   42.38-125.00-180.00   44
 17  ω     81.00 135.00   1.00    1.00    --  107.93 -77.00 120.00   54
 18  ω     34.00  63.00   1.00    1.00    --  107.93 -30.00-120.00   29
 19  ω     39.00  65.00   1.00    1.00    --  107.93 -30.00-150.00   26
 20  ω     62.00  96.00   1.00    1.00    --  107.93 -94.00   0.00   34
 21  ω    125.00 151.00   1.00    1.00    --  107.93  45.00-120.00   26
 22  ω     89.00 115.00   1.00    1.00    --  107.93-125.00 -90.00   26
 23  ω     39.00  70.00   1.00    1.00    --  107.93 -45.00  60.00   31
 24  ω    104.00 130.00   1.00    1.00    --  107.93 -61.00 -60.00   26
 25  ω    110.00 149.00   1.00    1.00    --  107.93  61.00 -30.00   39
 26  ω     39.00 118.00   1.00    1.00    --  107.93-125.00 120.00   79
 27  ω     40.00  73.00   1.00    1.00    --  107.93 -61.00 -60.00   33
 28  ω     41.00  66.00   1.00    1.00    --  107.93 -30.00 120.00   25
 29  ω     94.00 120.00   1.00    1.00    --  107.93  45.00-120.00   26
 30  ω     41.00  67.00   1.00    1.00    --  107.93 -45.00 150.00   26
 31  ω     55.00 114.00   1.00    1.00    --  107.93-125.00 -30.00   59
 32  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00  60.00  109
 33  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00 150.00  109
 34  ω   -116.00 -14.00   1.00    1.00    --  -42.38 -57.00 -60.00  102
 35  ω     10.00  70.00   1.00    1.00    --   42.38  77.00 -60.00   60
 36  ω    -30.00  71.00   1.00    1.00    --   42.38 -57.00  90.00  101
 37  ω     10.00 119.00   1.00    1.00    --   42.38  77.00-150.00  109
;


#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 shelx_SHELXL_version_number            2018/3

 The Friedel pair coverage of the experiment is almost complete (100%).
 Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2009).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
 is inverted is smaller than 10-99. The absolute structure parameter y 
 (Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
 2010). The resulting value was y=0.01(4), which together with Flack
 parameter value, indicate that the absolute structure has sureley been
 determined correctly.

 Flack, H. D. (1983), Acta Cryst. A39, 876-881
 Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;  
 H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

 R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 
 96-103
 Dolomanov, O.V. (2009) OLEX2, J. Appl. Cryst., 42, 339-341. 
 Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
 Spek, A.L. (2009). Acta Cryst. D65, 148-155.
 A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
 A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
 A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.4640P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6308
_refine_ls_number_parameters     452
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
  The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=0.01(6)
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3869(2) 0.24168(13) 0.15523(5) 0.0483(4) Uani 1 1 d . . . . .
O2 O 0.30505(16) 0.34158(13) 0.21316(4) 0.0321(3) Uani 1 1 d . . . . .
O3 O 0.10504(14) 0.55136(13) 0.18359(4) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.59691(14) 0.64644(14) 0.16754(4) 0.0316(3) Uani 1 1 d . . . . .
O5 O 0.64421(15) 0.92740(13) 0.16660(5) 0.0355(3) Uani 1 1 d . . . . .
O6 O 1.10988(16) 0.94933(16) 0.13892(6) 0.0474(4) Uani 1 1 d . . . . .
O7 O 0.83947(16) 0.60807(14) 0.08861(5) 0.0418(4) Uani 1 1 d . . . . .
O8 O 0.21243(14) 0.41964(15) 0.05842(4) 0.0363(4) Uani 1 1 d . . . . .
O9 O 0.54389(14) 0.39859(14) 0.01168(4) 0.0333(3) Uani 1 1 d . . . . .
O10 O 0.40421(15) 0.25995(14) -0.13157(4) 0.0343(3) Uani 1 1 d . . . . .
O11 O 0.09583(13) 0.42113(13) -0.02891(4) 0.0281(3) Uani 1 1 d . . . . .
N1 N 0.32995(16) 0.56329(15) 0.17689(5) 0.0235(3) Uani 1 1 d D . . . .
N2 N 0.33673(18) 0.75744(16) 0.23149(5) 0.0313(4) Uani 1 1 d . . . . .
C1 C 0.3492(2) 0.33493(18) 0.17222(6) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.34028(19) 0.45782(17) 0.14828(6) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.256606 0.455561 0.130472 0.027 Uiso 1 1 calc R . . . .
C3 C 0.45672(19) 0.46723(17) 0.11563(6) 0.0227(4) Uani 1 1 d . . . . .
H3A H 0.541376 0.46869 0.132315 0.027 Uiso 1 1 calc R . . . .
H3B H 0.457262 0.392583 0.097084 0.027 Uiso 1 1 calc R . . . .
C4 C 0.45199(19) 0.57882(17) 0.08617(6) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.53293(19) 0.68317(17) 0.09349(6) 0.0241(4) Uani 1 1 d . . . . .
C6 C 0.5330(2) 0.78016(19) 0.06372(6) 0.0310(4) Uani 1 1 d . . . . .
H6 H 0.588987 0.849115 0.068851 0.037 Uiso 1 1 calc R . . . .
C7 C 0.4529(2) 0.7778(2) 0.02677(7) 0.0368(5) Uani 1 1 d . . . . .
H7 H 0.44991 0.846378 0.007544 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3775(2) 0.6743(2) 0.01822(6) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.325559 0.670398 -0.007802 0.039 Uiso 1 1 calc R . . . .
C9 C 0.37656(19) 0.57561(18) 0.04728(6) 0.0248(4) Uani 1 1 d . . . . .
C10 C 0.3031(3) 0.2269(2) 0.23735(7) 0.0400(5) Uani 1 1 d . . . . .
H10A H 0.254535 0.16477 0.220454 0.06 Uiso 1 1 calc GR . . . .
H10B H 0.258657 0.239563 0.265607 0.06 Uiso 1 1 calc GR . . . .
H10C H 0.394718 0.198999 0.242335 0.06 Uiso 1 1 calc GR . . . .
C11 C 0.21114(19) 0.60226(17) 0.19193(6) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.2160(2) 0.71635(17) 0.21970(6) 0.0254(4) Uani 1 1 d . . . . .
C13 C 0.0985(2) 0.7741(2) 0.23115(7) 0.0348(5) Uani 1 1 d . . . . .
H13 H 0.014888 0.742075 0.221955 0.042 Uiso 1 1 calc R . . . .
C14 C 0.1053(3) 0.8803(2) 0.25647(7) 0.0431(6) Uani 1 1 d . U . . .
H14 H 0.026373 0.922886 0.264624 0.052 Uiso 1 1 calc R . . . .
C15 C 0.2280(3) 0.9224(2) 0.26944(7) 0.0428(6) Uani 1 1 d . U . . .
H15 H 0.235445 0.993782 0.287211 0.051 Uiso 1 1 calc R . . . .
C16 C 0.3406(3) 0.8592(2) 0.25621(7) 0.0401(5) Uani 1 1 d . U . . .
H16 H 0.425219 0.889494 0.26511 0.048 Uiso 1 1 calc R . . . .
C17 C 0.6222(2) 0.69495(17) 0.13244(6) 0.0252(4) Uani 1 1 d . . . . .
C18 C 0.74785(19) 0.76879(18) 0.12859(6) 0.0254(4) Uani 1 1 d . . . . .
C19 C 0.7609(2) 0.88222(18) 0.15012(6) 0.0268(4) Uani 1 1 d . . . . .
C20 C 0.8827(2) 0.93998(19) 0.15321(7) 0.0323(4) Uani 1 1 d . . . . .
H20 H 0.891147 1.015639 0.168503 0.039 Uiso 1 1 calc R . . . .
C21 C 0.9934(2) 0.8856(2) 0.13355(7) 0.0340(5) Uani 1 1 d . . . . .
C22 C 0.9838(2) 0.7761(2) 0.11093(7) 0.0334(5) Uani 1 1 d . . . . .
H22 H 1.059643 0.740961 0.097118 0.04 Uiso 1 1 calc R . . . .
C23 C 0.8598(2) 0.71849(18) 0.10889(7) 0.0301(4) Uani 1 1 d . . . . .
C24 C 0.6520(3) 1.0324(2) 0.19485(8) 0.0409(5) Uani 1 1 d . . . . .
H24A H 0.696678 1.099862 0.179427 0.061 Uiso 1 1 calc GR . . . .
H24B H 0.70287 1.011133 0.221218 0.061 Uiso 1 1 calc GR . . . .
H24C H 0.561904 1.058078 0.203229 0.061 Uiso 1 1 calc GR . . . .
C25 C 1.2289(2) 0.8996(3) 0.12074(10) 0.0574(8) Uani 1 1 d . . . . .
H25A H 1.218209 0.890113 0.088982 0.086 Uiso 1 1 calc GR . . . .
H25B H 1.247012 0.819311 0.133982 0.086 Uiso 1 1 calc GR . . . .
H25C H 1.303555 0.955314 0.126719 0.086 Uiso 1 1 calc GR . . . .
C26 C 0.9544(3) 0.5322(2) 0.08164(8) 0.0478(6) Uani 1 1 d . . . . .
H26A H 1.010644 0.568883 0.058853 0.072 Uiso 1 1 calc GR . . . .
H26B H 0.925933 0.450115 0.072322 0.072 Uiso 1 1 calc GR . . . .
H26C H 1.005258 0.525764 0.108982 0.072 Uiso 1 1 calc GR . . . .
C27 C 0.29609(19) 0.46429(18) 0.03426(6) 0.0246(4) Uani 1 1 d . . . . .
C28 C 0.32284(18) 0.41202(17) -0.01007(6) 0.0226(4) Uani 1 1 d . . . . .
C29 C 0.4534(2) 0.38138(18) -0.02124(6) 0.0254(4) Uani 1 1 d . . . . .
C30 C 0.4865(2) 0.33032(18) -0.06134(6) 0.0277(4) Uani 1 1 d . . . . .
H30 H 0.576324 0.310502 -0.068295 0.033 Uiso 1 1 calc R . . . .
C31 C 0.3847(2) 0.30903(17) -0.09101(6) 0.0266(4) Uani 1 1 d . . . . .
C32 C 0.2523(2) 0.33504(18) -0.08093(6) 0.0259(4) Uani 1 1 d . . . . .
H32 H 0.183608 0.317432 -0.101453 0.031 Uiso 1 1 calc R . . . .
C33 C 0.22160(19) 0.38681(17) -0.04073(6) 0.0226(4) Uani 1 1 d . . . . .
C34 C 0.6803(2) 0.4131(2) -0.00009(8) 0.0402(5) Uani 1 1 d . . . . .
H34A H 0.687784 0.474474 -0.023469 0.06 Uiso 1 1 calc GR . . . .
H34B H 0.715727 0.334365 -0.010442 0.06 Uiso 1 1 calc GR . . . .
H34C H 0.731171 0.440446 0.025539 0.06 Uiso 1 1 calc GR . . . .
C35 C 0.5395(2) 0.2415(2) -0.14493(7) 0.0388(5) Uani 1 1 d . . . . .
H35A H 0.541205 0.204817 -0.174267 0.058 Uiso 1 1 calc GR . . . .
H35B H 0.584027 0.186436 -0.124153 0.058 Uiso 1 1 calc GR . . . .
H35C H 0.586022 0.320722 -0.145533 0.058 Uiso 1 1 calc GR . . . .
C36 C -0.0084(2) 0.3946(2) -0.05944(7) 0.0349(5) Uani 1 1 d . . . . .
H36A H 0.013093 0.431553 -0.087881 0.052 Uiso 1 1 calc GR . . . .
H36B H -0.092562 0.428748 -0.048578 0.052 Uiso 1 1 calc GR . . . .
H36C H -0.017138 0.305432 -0.062794 0.052 Uiso 1 1 calc GR . . . .
H1 H 0.4061(17) 0.604(2) 0.1849(8) 0.042 Uiso 1 1 d DR . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.201(2) . ?
O2 C1 1.327(2) . ?
O2 C10 1.449(2) . ?
O3 C11 1.226(2) . ?
O4 C17 1.220(2) . ?
O5 C19 1.365(2) . ?
O5 C24 1.434(2) . ?
O6 C21 1.368(3) . ?
O6 C25 1.423(3) . ?
O7 C23 1.367(2) . ?
O7 C26 1.434(3) . ?
O8 C27 1.218(2) . ?
O9 C29 1.366(2) . ?
O9 C34 1.423(3) . ?
O10 C31 1.362(2) . ?
O10 C35 1.431(3) . ?
O11 C33 1.364(2) . ?
O11 C36 1.429(2) . ?
N1 C2 1.445(2) . ?
N1 C11 1.346(2) . ?
N1 H1 0.917(13) . ?
N2 C12 1.340(3) . ?
N2 C16 1.340(3) . ?
C1 C2 1.526(3) . ?
C2 H2 1 . ?
C2 C3 1.538(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C3 C4 1.511(2) . ?
C4 C5 1.414(3) . ?
C4 C9 1.407(3) . ?
C5 C6 1.392(3) . ?
C5 C17 1.493(3) . ?
C6 H6 0.95 . ?
C6 C7 1.384(3) . ?
C7 H7 0.95 . ?
C7 C8 1.382(3) . ?
C8 H8 0.95 . ?
C8 C9 1.392(3) . ?
C9 C27 1.509(3) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.504(3) . ?
C12 C13 1.381(3) . ?
C13 H13 0.95 . ?
C13 C14 1.392(3) . ?
C14 H14 0.95 . ?
C14 C15 1.371(4) . ?
C15 H15 0.95 . ?
C15 C16 1.383(4) . ?
C16 H16 0.95 . ?
C17 C18 1.499(3) . ?
C18 C19 1.404(3) . ?
C18 C23 1.386(3) . ?
C19 C20 1.377(3) . ?
C20 H20 0.95 . ?
C20 C21 1.393(3) . ?
C21 C22 1.380(3) . ?
C22 H22 0.95 . ?
C22 C23 1.394(3) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 C28 1.491(2) . ?
C28 C29 1.394(3) . ?
C28 C33 1.407(3) . ?
C29 C30 1.384(3) . ?
C30 H30 0.95 . ?
C30 C31 1.384(3) . ?
C31 C32 1.392(3) . ?
C32 H32 0.95 . ?
C32 C33 1.384(3) . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
C35 H35A 0.98 . ?
C35 H35B 0.98 . ?
C35 H35C 0.98 . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C10 115.89(16) . . ?
C19 O5 C24 117.48(17) . . ?
C21 O6 C25 118.5(2) . . ?
C23 O7 C26 116.95(18) . . ?
C29 O9 C34 117.91(16) . . ?
C31 O10 C35 116.75(16) . . ?
C33 O11 C36 116.67(15) . . ?
C2 N1 H1 119.2(16) . . ?
C11 N1 C2 121.31(16) . . ?
C11 N1 H1 119.5(16) . . ?
C12 N2 C16 116.94(19) . . ?
O1 C1 O2 123.89(18) . . ?
O1 C1 C2 123.52(17) . . ?
O2 C1 C2 112.52(16) . . ?
N1 C2 C1 114.27(14) . . ?
N1 C2 H2 106.7 . . ?
N1 C2 C3 113.10(15) . . ?
C1 C2 H2 106.7 . . ?
C1 C2 C3 108.89(15) . . ?
C3 C2 H2 106.7 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.50(15) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C5 C4 C3 122.25(16) . . ?
C9 C4 C3 119.87(17) . . ?
C9 C4 C5 117.49(17) . . ?
C4 C5 C17 122.60(16) . . ?
C6 C5 C4 120.43(17) . . ?
C6 C5 C17 116.96(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.15(19) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.77(18) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C27 121.96(17) . . ?
C8 C9 C4 120.93(18) . . ?
C8 C9 C27 117.06(17) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N1 123.73(17) . . ?
O3 C11 C12 121.20(17) . . ?
N1 C11 C12 115.06(17) . . ?
N2 C12 C11 117.14(17) . . ?
N2 C12 C13 123.50(18) . . ?
C13 C12 C11 119.36(19) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.9(2) . . ?
C16 C15 H15 120.6 . . ?
N2 C16 C15 123.5(2) . . ?
N2 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
O4 C17 C5 122.43(17) . . ?
O4 C17 C18 118.37(17) . . ?
C5 C17 C18 119.20(16) . . ?
C19 C18 C17 120.86(17) . . ?
C23 C18 C17 120.21(17) . . ?
C23 C18 C19 118.31(18) . . ?
O5 C19 C18 114.12(17) . . ?
O5 C19 C20 124.82(18) . . ?
C20 C19 C18 121.06(19) . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 118.92(19) . . ?
C21 C20 H20 120.5 . . ?
O6 C21 C20 114.4(2) . . ?
O6 C21 C22 123.8(2) . . ?
C22 C21 C20 121.74(19) . . ?
C21 C22 H22 120.9 . . ?
C21 C22 C23 118.21(19) . . ?
C23 C22 H22 120.9 . . ?
O7 C23 C18 114.99(18) . . ?
O7 C23 C22 123.28(19) . . ?
C18 C23 C22 121.72(18) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C27 C9 121.98(17) . . ?
O8 C27 C28 121.37(18) . . ?
C28 C27 C9 116.65(16) . . ?
C29 C28 C27 118.81(16) . . ?
C29 C28 C33 117.97(16) . . ?
C33 C28 C27 123.16(17) . . ?
O9 C29 C28 114.31(16) . . ?
O9 C29 C30 123.05(18) . . ?
C30 C29 C28 122.51(18) . . ?
C29 C30 H30 121 . . ?
C29 C30 C31 117.90(18) . . ?
C31 C30 H30 121 . . ?
O10 C31 C30 123.60(18) . . ?
O10 C31 C32 114.68(17) . . ?
C30 C31 C32 121.71(17) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.35(17) . . ?
C33 C32 H32 120.3 . . ?
O11 C33 C28 115.99(16) . . ?
O11 C33 C32 123.44(17) . . ?
C32 C33 C28 120.52(17) . . ?
O9 C34 H34A 109.5 . . ?
O9 C34 H34B 109.5 . . ?
O9 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O10 C35 H35A 109.5 . . ?
O10 C35 H35B 109.5 . . ?
O10 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O11 C36 H36A 109.5 . . ?
O11 C36 H36B 109.5 . . ?
O11 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -163.1(2) . . . . ?
O1 C1 C2 C3 -35.6(3) . . . . ?
O2 C1 C2 N1 19.7(2) . . . . ?
O2 C1 C2 C3 147.22(16) . . . . ?
O3 C11 C12 N2 172.25(18) . . . . ?
O3 C11 C12 C13 -8.7(3) . . . . ?
O4 C17 C18 C19 -70.3(3) . . . . ?
O4 C17 C18 C23 100.5(2) . . . . ?
O5 C19 C20 C21 -177.74(19) . . . . ?
O6 C21 C22 C23 178.16(19) . . . . ?
O8 C27 C28 C29 -126.9(2) . . . . ?
O8 C27 C28 C33 50.2(3) . . . . ?
O9 C29 C30 C31 175.33(18) . . . . ?
O10 C31 C32 C33 -179.10(17) . . . . ?
N1 C2 C3 C4 -58.0(2) . . . . ?
N1 C11 C12 N2 -8.8(2) . . . . ?
N1 C11 C12 C13 170.27(17) . . . . ?
N2 C12 C13 C14 -0.3(3) . . . . ?
C1 C2 C3 C4 173.83(15) . . . . ?
C2 N1 C11 O3 1.6(3) . . . . ?
C2 N1 C11 C12 -177.39(15) . . . . ?
C2 C3 C4 C5 102.5(2) . . . . ?
C2 C3 C4 C9 -84.9(2) . . . . ?
C3 C4 C5 C6 175.07(17) . . . . ?
C3 C4 C5 C17 -4.3(3) . . . . ?
C3 C4 C9 C8 -175.85(18) . . . . ?
C3 C4 C9 C27 1.6(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C4 C5 C17 O4 -29.7(3) . . . . ?
C4 C5 C17 C18 150.19(18) . . . . ?
C4 C9 C27 O8 55.3(3) . . . . ?
C4 C9 C27 C28 -125.42(19) . . . . ?
C5 C4 C9 C8 -2.8(3) . . . . ?
C5 C4 C9 C27 174.64(17) . . . . ?
C5 C6 C7 C8 -3.6(3) . . . . ?
C5 C17 C18 C19 109.8(2) . . . . ?
C5 C17 C18 C23 -79.4(2) . . . . ?
C6 C5 C17 O4 150.86(19) . . . . ?
C6 C5 C17 C18 -29.2(3) . . . . ?
C6 C7 C8 C9 3.0(3) . . . . ?
C7 C8 C9 C4 0.2(3) . . . . ?
C7 C8 C9 C27 -177.35(19) . . . . ?
C8 C9 C27 O8 -127.2(2) . . . . ?
C8 C9 C27 C28 52.1(2) . . . . ?
C9 C4 C5 C6 2.2(3) . . . . ?
C9 C4 C5 C17 -177.16(17) . . . . ?
C9 C27 C28 C29 53.8(2) . . . . ?
C9 C27 C28 C33 -129.10(19) . . . . ?
C10 O2 C1 O1 -0.6(3) . . . . ?
C10 O2 C1 C2 176.62(17) . . . . ?
C11 N1 C2 C1 -86.4(2) . . . . ?
C11 N1 C2 C3 148.26(17) . . . . ?
C11 C12 C13 C14 -179.31(18) . . . . ?
C12 N2 C16 C15 -0.5(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 N2 -0.6(4) . . . . ?
C16 N2 C12 C11 179.94(17) . . . . ?
C16 N2 C12 C13 0.9(3) . . . . ?
C17 C5 C6 C7 -179.62(19) . . . . ?
C17 C18 C19 O5 -12.1(3) . . . . ?
C17 C18 C19 C20 168.41(19) . . . . ?
C17 C18 C23 O7 8.9(3) . . . . ?
C17 C18 C23 C22 -169.54(18) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C19 C18 C23 O7 179.98(17) . . . . ?
C19 C18 C23 C22 1.5(3) . . . . ?
C19 C20 C21 O6 -179.24(18) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 -1.4(3) . . . . ?
C21 C22 C23 O7 -177.90(18) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C23 C18 C19 O5 176.88(18) . . . . ?
C23 C18 C19 C20 -2.6(3) . . . . ?
C24 O5 C19 C18 170.42(17) . . . . ?
C24 O5 C19 C20 -10.1(3) . . . . ?
C25 O6 C21 C20 178.7(2) . . . . ?
C25 O6 C21 C22 -0.9(3) . . . . ?
C26 O7 C23 C18 -158.5(2) . . . . ?
C26 O7 C23 C22 20.0(3) . . . . ?
C27 C28 C29 O9 2.8(3) . . . . ?
C27 C28 C29 C30 178.76(18) . . . . ?
C27 C28 C33 O11 4.5(3) . . . . ?
C27 C28 C33 C32 -178.17(18) . . . . ?
C28 C29 C30 C31 -0.3(3) . . . . ?
C29 C28 C33 O11 -178.39(17) . . . . ?
C29 C28 C33 C32 -1.1(3) . . . . ?
C29 C30 C31 O10 179.62(18) . . . . ?
C29 C30 C31 C32 -1.4(3) . . . . ?
C30 C31 C32 C33 1.9(3) . . . . ?
C31 C32 C33 O11 176.55(18) . . . . ?
C31 C32 C33 C28 -0.6(3) . . . . ?
C33 C28 C29 O9 -174.46(16) . . . . ?
C33 C28 C29 C30 1.5(3) . . . . ?
C34 O9 C29 C28 -157.8(2) . . . . ?
C34 O9 C29 C30 26.2(3) . . . . ?
C35 O10 C31 C30 -6.3(3) . . . . ?
C35 O10 C31 C32 174.74(18) . . . . ?
C36 O11 C33 C28 -179.17(17) . . . . ?
C36 O11 C33 C32 3.6(3) . . . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_a20190132_acn1250b
_database_code_depnum_ccdc_archive 'CCDC 1939206'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad del Pais Vasco
Spain
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2019-04-17T11:54:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H13 Br2 Cl N2 O3'
_chemical_formula_sum            'C16 H13 Br2 Cl N2 O3'
_chemical_formula_weight         476.55
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.22428(16)
_cell_length_b                   13.92307(19)
_cell_length_c                   8.40898(16)
_cell_angle_alpha                90
_cell_angle_beta                 115.927(2)
_cell_angle_gamma                90
_cell_volume                     865.97(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    7774
_cell_measurement_theta_min      5.828
_cell_measurement_theta_max      74.097

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.094
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_F_000             468
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.1665
5 -3 -4 0.07
-2 -1 -3 0.1874
-5 3 4 0.0453
-1 9 1 0.0096
-1 -9 0 0.0505


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.522
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.211
_exptl_absorpt_correction_T_max  0.655

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0744593
_diffrn_orient_matrix_ub_12      0.1019737
_diffrn_orient_matrix_ub_13      0.0041401
_diffrn_orient_matrix_ub_21      -0.1721142
_diffrn_orient_matrix_ub_22      0.026197
_diffrn_orient_matrix_ub_23      -0.1672409
_diffrn_orient_matrix_ub_31      -0.0906358
_diffrn_orient_matrix_ub_32      0.0340257
_diffrn_orient_matrix_ub_33      0.1162532
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_number            9363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.851
_diffrn_reflns_theta_max         68.958
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_coverage         0.913
_reflns_number_total             3199
_reflns_number_gt                3134
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  83.00   1.00    1.00    --   42.13 -19.00   0.00   95
  2  ω     32.00 102.00   1.00    1.00    --   42.13  38.00   0.00   70
  3  ω     16.00 103.00   1.00    1.00    --   42.13  57.00-150.00   87
  4  ω     18.00  56.00   1.00    1.00    --   42.13  38.00 -30.00   38
  5  ω    -15.00  51.00   1.00    1.00    --   42.13 -77.00-180.00   66
  6  ω     47.00 112.00   1.00    1.00    --  107.93-125.00  60.00   65
  7  ω     52.00  87.00   1.00    1.00    --  107.93 -94.00  90.00   35
  8  ω     79.00 155.00   1.00    1.00    --  107.93  61.00  60.00   76
  9  ω     32.00  64.00   1.00    1.00    --  107.93 -30.00  30.00   32
 10  ω     82.00 155.00   1.00    1.00    --  107.93  45.00   0.00   73
 11  ω     35.00  77.00   1.00    1.00    --  107.93 -45.00  90.00   42
 12  ω     35.00  61.00   1.00    1.00    --  107.93 -45.00-120.00   26
 13  ω     36.00  66.00   1.00    1.00    --  107.93 -30.00 120.00   30
 14  ω     37.00  99.00   1.00    1.00    --  107.93 -94.00 -90.00   62
 15  ω     35.00  67.00   1.00    1.00    --  107.93 -30.00 -60.00   32
 16  ω     40.00  66.00   1.00    1.00    --  107.93 -30.00-120.00   26
 17  ω     32.00  57.00   1.00    1.00    --  107.93 -30.00  60.00   25
 18  ω     34.00  64.00   1.00    1.00    --  107.93 -30.00-180.00   30
 19  ω     38.00  63.00   1.00    1.00    --  107.93 -30.00 150.00   25
 20  ω     70.00 118.00   1.00    1.00    --  107.93-125.00-150.00   48
 21  ω     48.00  91.00   1.00    1.00    --  107.93 -94.00-150.00   43
 22  ω     73.00 154.00   1.00    1.00    --  107.93 125.00-180.00   81
 23  ω     48.00  93.00   1.00    1.00    --   42.13-125.00  60.00   45
 24  ω     12.00  38.00   1.00    1.00    --   42.13-125.00  60.00   26
 25  ω     32.00  57.00   1.00    1.00    --  107.93 -30.00 -30.00   25
 26  ω     34.00  81.00   1.00    1.00    --  107.93 -94.00 -30.00   47
 27  ω    107.00 142.00   1.00    1.00    --  107.93  45.00 -60.00   35
 28  ω     20.00  50.00   1.00    1.00    --  107.93   0.00 -90.00   30
 29  ω    -70.00  31.00   1.00    1.00    --  -42.13  57.00 -30.00  101
 30  ω   -118.00 -10.00   1.00    1.00    --  -42.13 -77.00  90.00  108
 31  ω   -118.00 -10.00   1.00    1.00    --  -42.13 -77.00 -30.00  108
 32  ω   -118.00 -10.00   1.00    1.00    --  -42.13 -77.00-150.00  108
 33  ω     10.00 118.00   1.00    1.00    --   42.13  77.00 120.00  108
 34  ω     14.00 115.00   1.00    1.00    --   42.13  57.00  90.00  101
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 shelx_SHELXL_version_number            2018/3

 The Friedel pair coverage of the experiment is almost complete (100%).
 Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2009).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
 is inverted is smaller than 10-99. The absolute structure parameter y 
 (Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
 2010). The resulting value was y=0.005(17), which together with Flack
 parameter value, indicate that the absolute structure has sureley been
 determined correctly.

 Flack, H. D. (1983), Acta Cryst. A39, 876-881
 Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;  
 H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

 R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 
 96-103
 Dolomanov, O.V. (2009) OLEX2, J. Appl. Cryst., 42, 339-341. 
 Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
 Spek, A.L. (2009). Acta Cryst. D65, 148-155.
 A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
 A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
 A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.072
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.005(107)
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.32860(7) 0.45636(4) 1.02403(7) 0.02716(15) Uani 1 1 d . . . . .
Br2 Br 0.84180(7) 0.52658(5) 0.74644(7) 0.03350(17) Uani 1 1 d . . . . .
Cl1 Cl 0.94087(19) 0.66908(10) 1.3902(2) 0.0341(3) Uani 1 1 d . . . . .
O1 O 0.0038(6) 0.4100(3) 0.5393(5) 0.0304(9) Uani 1 1 d . . . . .
O2 O 0.3894(5) 0.6017(3) 0.3880(5) 0.0260(8) Uani 1 1 d . . . . .
O3 O 0.4541(5) 0.6646(3) 0.6546(5) 0.0231(8) Uani 1 1 d . . . . .
N1 N 0.2066(5) 0.4543(4) 0.4383(5) 0.0211(8) Uani 1 1 d . . . . .
H1 H 0.238227 0.44972 0.351234 0.025 Uiso 1 1 calc R . . . .
N2 N 0.0260(6) 0.3551(3) 0.1371(6) 0.0238(10) Uani 1 1 d . . . . .
C1 C 0.0573(7) 0.4087(3) 0.4246(7) 0.0200(11) Uani 1 1 d . . . . .
C2 C -0.0430(7) 0.3535(3) 0.2547(7) 0.0217(11) Uani 1 1 d . . . . .
C3 C -0.0629(8) 0.3060(4) -0.0122(8) 0.0305(13) Uani 1 1 d . . . . .
H3 H -0.016361 0.306225 -0.097599 0.037 Uiso 1 1 calc R . . . .
C4 C -0.2199(8) 0.2544(4) -0.0496(7) 0.0308(13) Uani 1 1 d . . . . .
H4 H -0.279285 0.22067 -0.158095 0.037 Uiso 1 1 calc R . . . .
C5 C -0.2881(8) 0.2533(4) 0.0744(8) 0.0353(15) Uani 1 1 d . . . . .
H5 H -0.395215 0.218676 0.053205 0.042 Uiso 1 1 calc R . . . .
C6 C -0.1964(7) 0.3036(4) 0.2300(7) 0.0271(13) Uani 1 1 d . . . . .
H6 H -0.238734 0.303786 0.318523 0.033 Uiso 1 1 calc R . . . .
C7 C 0.3171(6) 0.5108(3) 0.5928(6) 0.0169(10) Uani 1 1 d . . . . .
H7 H 0.239569 0.534944 0.648513 0.02 Uiso 1 1 calc R . . . .
C8 C 0.4708(7) 0.4483(4) 0.7289(6) 0.0208(10) Uani 1 1 d . . . . .
H8A H 0.416083 0.392223 0.759611 0.025 Uiso 1 1 calc R . . . .
H8B H 0.545698 0.423553 0.672246 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5918(7) 0.4991(3) 0.8961(7) 0.0179(9) Uani 1 1 d . . . . .
C10 C 0.5465(6) 0.5114(3) 1.0368(6) 0.0194(10) Uani 1 1 d . . . . .
C11 C 0.6501(7) 0.5620(4) 1.1892(7) 0.0206(10) Uani 1 1 d . . . . .
H11 H 0.612368 0.569596 1.280339 0.025 Uiso 1 1 calc R . . . .
C12 C 0.8096(7) 0.6011(4) 1.2041(7) 0.0225(11) Uani 1 1 d . . . . .
C13 C 0.8678(7) 0.5896(4) 1.0733(7) 0.0224(11) Uani 1 1 d . . . . .
H13 H 0.980288 0.615053 1.086813 0.027 Uiso 1 1 calc R . . . .
C14 C 0.7566(7) 0.5398(4) 0.9228(7) 0.0207(10) Uani 1 1 d . . . . .
C15 C 0.3890(7) 0.5962(4) 0.5303(7) 0.0202(11) Uani 1 1 d . . . . .
C16 C 0.5376(9) 0.7450(4) 0.6110(9) 0.0361(14) Uani 1 1 d . . . . .
H16A H 0.445881 0.780316 0.511283 0.054 Uiso 1 1 calc GR . . . .
H16B H 0.631422 0.721645 0.578499 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.592146 0.787736 0.713528 0.054 Uiso 1 1 calc GR . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.908(5) . ?
Br2 C14 1.906(5) . ?
Cl1 C12 1.742(6) . ?
O1 C1 1.223(7) . ?
O2 C15 1.200(6) . ?
O3 C15 1.341(6) . ?
O3 C16 1.442(6) . ?
N1 H1 0.88 . ?
N1 C1 1.341(7) . ?
N1 C7 1.450(6) . ?
N2 C2 1.339(7) . ?
N2 C3 1.333(7) . ?
C1 C2 1.510(7) . ?
C2 C6 1.374(7) . ?
C3 H3 0.95 . ?
C3 C4 1.387(8) . ?
C4 H4 0.95 . ?
C4 C5 1.384(9) . ?
C5 H5 0.95 . ?
C5 C6 1.382(8) . ?
C6 H6 0.95 . ?
C7 H7 1 . ?
C7 C8 1.550(6) . ?
C7 C15 1.519(7) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C8 C9 1.499(7) . ?
C9 C10 1.397(7) . ?
C9 C14 1.394(7) . ?
C10 C11 1.383(7) . ?
C11 H11 0.95 . ?
C11 C12 1.374(7) . ?
C12 C13 1.388(8) . ?
C13 H13 0.95 . ?
C13 C14 1.380(8) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?

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
C15 O3 C16 115.2(4) . . ?
C1 N1 H1 119.1 . . ?
C1 N1 C7 121.7(4) . . ?
C7 N1 H1 119.1 . . ?
C3 N2 C2 116.9(5) . . ?
O1 C1 N1 123.8(5) . . ?
O1 C1 C2 121.2(5) . . ?
N1 C1 C2 115.0(4) . . ?
N2 C2 C1 117.2(5) . . ?
N2 C2 C6 123.7(5) . . ?
C6 C2 C1 119.1(5) . . ?
N2 C3 H3 118.3 . . ?
N2 C3 C4 123.5(6) . . ?
C4 C3 H3 118.3 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.3(6) . . ?
C6 C5 H5 120.8 . . ?
C2 C6 C5 119.0(6) . . ?
C2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C8 110.2(4) . . ?
N1 C7 C15 107.5(4) . . ?
C8 C7 H7 108.9 . . ?
C15 C7 H7 108.9 . . ?
C15 C7 C8 112.3(4) . . ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 114.8(4) . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C10 C9 C8 122.6(5) . . ?
C14 C9 C8 122.9(5) . . ?
C14 C9 C10 114.5(4) . . ?
C9 C10 Br1 119.7(4) . . ?
C11 C10 Br1 116.1(4) . . ?
C11 C10 C9 124.2(5) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.6(5) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 Cl1 119.3(4) . . ?
C11 C12 C13 121.9(5) . . ?
C13 C12 Cl1 118.8(4) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.7(5) . . ?
C14 C13 H13 121.2 . . ?
C9 C14 Br2 119.9(4) . . ?
C13 C14 Br2 116.1(4) . . ?
C13 C14 C9 124.0(5) . . ?
O2 C15 O3 123.9(5) . . ?
O2 C15 C7 124.5(5) . . ?
O3 C15 C7 111.7(4) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Br1 C10 C11 C12 178.8(4) . . . . ?
Cl1 C12 C13 C14 -176.5(4) . . . . ?
O1 C1 C2 N2 -179.3(5) . . . . ?
O1 C1 C2 C6 -0.4(8) . . . . ?
N1 C1 C2 N2 0.3(7) . . . . ?
N1 C1 C2 C6 179.2(5) . . . . ?
N1 C7 C8 C9 -178.8(4) . . . . ?
N1 C7 C15 O2 -16.2(7) . . . . ?
N1 C7 C15 O3 164.5(4) . . . . ?
N2 C2 C6 C5 -1.2(8) . . . . ?
N2 C3 C4 C5 -0.3(9) . . . . ?
C1 N1 C7 C8 92.6(6) . . . . ?
C1 N1 C7 C15 -144.7(5) . . . . ?
C1 C2 C6 C5 179.9(5) . . . . ?
C2 N2 C3 C4 -0.1(8) . . . . ?
C3 N2 C2 C1 179.8(4) . . . . ?
C3 N2 C2 C6 0.9(8) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C4 C5 C6 C2 0.7(8) . . . . ?
C7 N1 C1 O1 -0.8(8) . . . . ?
C7 N1 C1 C2 179.6(4) . . . . ?
C7 C8 C9 C10 82.3(6) . . . . ?
C7 C8 C9 C14 -96.4(6) . . . . ?
C8 C7 C15 O2 105.2(6) . . . . ?
C8 C7 C15 O3 -74.1(5) . . . . ?
C8 C9 C10 Br1 3.2(6) . . . . ?
C8 C9 C10 C11 -176.6(5) . . . . ?
C8 C9 C14 Br2 -3.0(7) . . . . ?
C8 C9 C14 C13 177.9(5) . . . . ?
C9 C10 C11 C12 -1.4(8) . . . . ?
C10 C9 C14 Br2 178.3(4) . . . . ?
C10 C9 C14 C13 -0.8(7) . . . . ?
C10 C11 C12 Cl1 177.8(4) . . . . ?
C10 C11 C12 C13 -0.9(8) . . . . ?
C11 C12 C13 C14 2.1(8) . . . . ?
C12 C13 C14 Br2 179.7(4) . . . . ?
C12 C13 C14 C9 -1.3(8) . . . . ?
C14 C9 C10 Br1 -178.0(4) . . . . ?
C14 C9 C10 C11 2.2(7) . . . . ?
C15 C7 C8 C9 61.3(6) . . . . ?
C16 O3 C15 O2 -3.8(7) . . . . ?
C16 O3 C15 C7 175.5(4) . . . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
