# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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__PyChalconOMeHCl1
_database_code_depnum_ccdc_archive 'CCDC 1006003'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C15 H16 Cl N O3 '
_chemical_formula_moiety         'C15 H16 Cl N O3 '
_chemical_formula_weight         293.75
_chemical_melting_point          ?

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   5.19126(15)
_cell_length_b                   33.4280(10)
_cell_length_c                   9.2170(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.0213(14)
_cell_angle_gamma                90.0000
_cell_volume                     1482.77(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10511
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      68.2
_cell_measurement_temperature    298.1

#------------------------------------------------------------------------------

_exptl_crystal_description       block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            23293
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_theta_max         68.24
_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11


#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2669
_reflns_number_gt                2103
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1510
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     191
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0775P)²+0.2230P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.364 0.702
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================

# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl(1) Cl 1.14119(15) 0.03230(2) 0.24460(8) 0.0838(2) Uani 1.00 1 d . . .
O(1) O 0.8788(4) 0.15163(6) 0.9510(2) 0.0924(6) Uani 1.00 1 d . . .
O(2) O 1.5668(3) 0.21522(5) 0.28908(19) 0.0750(4) Uani 1.00 1 d . . .
O(3) O 0.7312(6) 0.07472(10) 0.3789(3) 0.1324(11) Uani 1.00 1 d . . .
N(1) N 0.2710(4) 0.03496(6) 0.7998(2) 0.0703(5) Uani 1.00 1 d . . .
C(1) C 0.3417(5) 0.04232(8) 0.6780(3) 0.0735(6) Uani 1.00 1 d . . .
C(2) C 0.5233(5) 0.07262(7) 0.6852(2) 0.0653(5) Uani 1.00 1 d . . .
C(3) C 0.6316(4) 0.09541(6) 0.8192(2) 0.0564(5) Uani 1.00 1 d . . .
C(4) C 0.5557(5) 0.08610(7) 0.9444(2) 0.0693(6) Uani 1.00 1 d . . .
C(5) C 0.3722(5) 0.05594(8) 0.9315(3) 0.0754(6) Uani 1.00 1 d . . .
C(6) C 0.8241(4) 0.13067(7) 0.8358(2) 0.0604(5) Uani 1.00 1 d . . .
C(7) C 0.9324(4) 0.13784(6) 0.7136(2) 0.0587(5) Uani 1.00 1 d . . .
C(8) C 1.0864(4) 0.16987(6) 0.7154(2) 0.0590(5) Uani 1.00 1 d . . .
C(9) C 1.2088(4) 0.18023(6) 0.6029(2) 0.0554(5) Uani 1.00 1 d . . .
C(10) C 1.3665(5) 0.21495(6) 0.6227(2) 0.0653(5) Uani 1.00 1 d . . .
C(11) C 1.4811(5) 0.22584(6) 0.5171(2) 0.0704(6) Uani 1.00 1 d . . .
C(12) C 1.4457(4) 0.20208(6) 0.3879(2) 0.0587(5) Uani 1.00 1 d . . .
C(13) C 1.2942(4) 0.16702(7) 0.3674(2) 0.0633(5) Uani 1.00 1 d . . .
C(14) C 1.1780(4) 0.15662(7) 0.4731(2) 0.0628(5) Uani 1.00 1 d . . .
C(15) C 1.5554(6) 0.18981(8) 0.1628(2) 0.0805(7) Uani 1.00 1 d . . .
H(1) H 0.1556 0.0159 0.7932 0.084 Uiso 1.00 1 c R . .
H(2) H 0.2678 0.0269 0.5879 0.088 Uiso 1.00 1 c R . .
H(3) H 0.5734 0.0778 0.6001 0.078 Uiso 1.00 1 c R . .
H(4) H 0.6302 0.1005 1.0372 0.083 Uiso 1.00 1 c R . .
H(5) H 0.3180 0.0501 1.0145 0.090 Uiso 1.00 1 c R . .
H(6) H 0.8930 0.1196 0.6320 0.070 Uiso 1.00 1 c R . .
H(7) H 1.1188 0.1875 0.7983 0.071 Uiso 1.00 1 c R . .
H(8) H 1.3944 0.2311 0.7096 0.078 Uiso 1.00 1 c R . .
H(9) H 1.5835 0.2494 0.5321 0.084 Uiso 1.00 1 c R . .
H(10) H 1.2714 0.1506 0.2820 0.076 Uiso 1.00 1 c R . .
H(11) H 1.0755 0.1331 0.4577 0.075 Uiso 1.00 1 c R . .
H(12) H 1.7151 0.1726 0.1956 0.097 Uiso 1.00 1 c R . .
H(13) H 1.5538 0.2058 0.0760 0.097 Uiso 1.00 1 c R . .
H(14) H 1.3896 0.1739 0.1316 0.097 Uiso 1.00 1 c R . .
H(15) H 0.821(10) 0.0630(12) 0.339(5) 0.148(17) Uiso 1.00 1 c . . .
H(16) H 0.568(11) 0.0640(13) 0.333(5) 0.154(16) Uiso 1.00 1 c . . .



#==============================================================================

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  SHELXL
_computing_publication_material  'CrystalStructure 3.8'
_computing_molecular_graphics    ?

#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O(1) C(6) 1.213(2) yes . .
O(2) C(12) 1.359(3) yes . .
O(2) C(15) 1.424(3) yes . .
N(1) C(1) 1.329(4) yes . .
N(1) C(5) 1.327(3) yes . .
C(1) C(2) 1.368(3) yes . .
C(2) C(3) 1.379(2) yes . .
C(3) C(4) 1.387(3) yes . .
C(3) C(6) 1.515(3) yes . .
C(4) C(5) 1.361(3) yes . .
C(6) C(7) 1.455(3) yes . .
C(7) C(8) 1.332(3) yes . .
C(8) C(9) 1.447(3) yes . .
C(9) C(10) 1.392(3) yes . .
C(9) C(14) 1.392(3) yes . .
C(10) C(11) 1.366(4) yes . .
C(11) C(12) 1.385(3) yes . .
C(12) C(13) 1.384(3) yes . .
C(13) C(14) 1.369(3) yes . .
O(3) H(15) 0.80(5) no . .
O(3) H(16) 0.87(4) no . .
N(1) H(1) 0.860 no . .
C(1) H(2) 0.930 no . .
C(2) H(3) 0.930 no . .
C(4) H(4) 0.930 no . .
C(5) H(5) 0.930 no . .
C(7) H(6) 0.930 no . .
C(8) H(7) 0.930 no . .
C(10) H(8) 0.930 no . .
C(11) H(9) 0.930 no . .
C(13) H(10) 0.930 no . .
C(14) H(11) 0.930 no . .
C(15) H(12) 0.960 no . .
C(15) H(13) 0.960 no . .
C(15) H(14) 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C(12) O(2) C(15) 117.84(19) yes . . .
C(1) N(1) C(5) 122.3(2) yes . . .
N(1) C(1) C(2) 120.0(2) yes . . .
C(1) C(2) C(3) 119.6(2) yes . . .
C(2) C(3) C(4) 118.3(2) yes . . .
C(2) C(3) C(6) 123.5(2) yes . . .
C(4) C(3) C(6) 118.20(18) yes . . .
C(3) C(4) C(5) 120.1(2) yes . . .
N(1) C(5) C(4) 119.7(2) yes . . .
O(1) C(6) C(3) 117.8(2) yes . . .
O(1) C(6) C(7) 123.4(2) yes . . .
C(3) C(6) C(7) 118.76(18) yes . . .
C(6) C(7) C(8) 121.8(2) yes . . .
C(7) C(8) C(9) 127.3(2) yes . . .
C(8) C(9) C(10) 120.03(19) yes . . .
C(8) C(9) C(14) 122.74(19) yes . . .
C(10) C(9) C(14) 117.2(2) yes . . .
C(9) C(10) C(11) 121.4(2) yes . . .
C(10) C(11) C(12) 120.4(2) yes . . .
O(2) C(12) C(11) 116.44(19) yes . . .
O(2) C(12) C(13) 124.3(2) yes . . .
C(11) C(12) C(13) 119.2(2) yes . . .
C(12) C(13) C(14) 119.8(2) yes . . .
C(9) C(14) C(13) 121.9(2) yes . . .
H(15) O(3) H(16) 102(4) no . . .
C(1) N(1) H(1) 118.8 no . . .
C(5) N(1) H(1) 118.8 no . . .
N(1) C(1) H(2) 120.0 no . . .
C(2) C(1) H(2) 120.0 no . . .
C(1) C(2) H(3) 120.2 no . . .
C(3) C(2) H(3) 120.2 no . . .
C(3) C(4) H(4) 120.0 no . . .
C(5) C(4) H(4) 120.0 no . . .
N(1) C(5) H(5) 120.2 no . . .
C(4) C(5) H(5) 120.1 no . . .
C(6) C(7) H(6) 119.1 no . . .
C(8) C(7) H(6) 119.1 no . . .
C(7) C(8) H(7) 116.4 no . . .
C(9) C(8) H(7) 116.4 no . . .
C(9) C(10) H(8) 119.3 no . . .
C(11) C(10) H(8) 119.3 no . . .
C(10) C(11) H(9) 119.8 no . . .
C(12) C(11) H(9) 119.8 no . . .
C(12) C(13) H(10) 120.1 no . . .
C(14) C(13) H(10) 120.1 no . . .
C(9) C(14) H(11) 119.0 no . . .
C(13) C(14) H(11) 119.0 no . . .
O(2) C(15) H(12) 109.5 no . . .
O(2) C(15) H(13) 109.5 no . . .
O(2) C(15) H(14) 109.5 no . . .
H(12) C(15) H(13) 109.5 no . . .
H(12) C(15) H(14) 109.5 no . . .
H(13) C(15) H(14) 109.5 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C(15) O(2) C(12) C(11) 174.55(19) ? . . . .
C(15) O(2) C(12) C(13) -5.0(2) ? . . . .
C(1) N(1) C(5) C(4) -0.2(3) ? . . . .
C(5) N(1) C(1) C(2) -0.5(3) ? . . . .
N(1) C(1) C(2) C(3) -0.1(2) ? . . . .
C(1) C(2) C(3) C(4) 1.3(3) ? . . . .
C(1) C(2) C(3) C(6) -177.3(2) ? . . . .
C(2) C(3) C(4) C(5) -2.0(3) ? . . . .
C(2) C(3) C(6) O(1) 170.9(2) ? . . . .
C(2) C(3) C(6) C(7) -8.8(3) ? . . . .
C(4) C(3) C(6) O(1) -7.7(3) ? . . . .
C(4) C(3) C(6) C(7) 172.63(19) ? . . . .
C(6) C(3) C(4) C(5) 176.7(2) ? . . . .
C(3) C(4) C(5) N(1) 1.4(3) ? . . . .
O(1) C(6) C(7) C(8) -4.5(3) ? . . . .
C(3) C(6) C(7) C(8) 175.15(18) ? . . . .
C(6) C(7) C(8) C(9) 179.19(19) ? . . . .
C(7) C(8) C(9) C(10) -179.6(2) ? . . . .
C(7) C(8) C(9) C(14) -0.0(2) ? . . . .
C(8) C(9) C(10) C(11) -179.0(2) ? . . . .
C(8) C(9) C(14) C(13) 179.65(19) ? . . . .
C(10) C(9) C(14) C(13) -0.7(3) ? . . . .
C(14) C(9) C(10) C(11) 1.4(3) ? . . . .
C(9) C(10) C(11) C(12) -0.9(3) ? . . . .
C(10) C(11) C(12) O(2) 179.98(16) ? . . . .
C(10) C(11) C(12) C(13) -0.4(3) ? . . . .
O(2) C(12) C(13) C(14) -179.36(19) ? . . . .
C(11) C(12) C(13) C(14) 1.1(3) ? . . . .
C(12) C(13) C(14) C(9) -0.5(3) ? . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cl(1) O(3) 3.169(3) ? . .
Cl(1) O(3) 3.175(3) ? . 1_655
Cl(1) N(1) 3.024(2) ? . 3_656
Cl(1) C(1) 3.536(2) ? . 3_756
O(1) C(15) 3.274(4) ? . 1_456
O(1) C(15) 3.555(3) ? . 1_556
O(2) C(10) 3.466(3) ? . 4_554
O(2) C(14) 3.570(2) ? . 1_655
O(3) Cl(1) 3.175(3) ? . 1_455
O(3) Cl(1) 3.169(3) ? . .
O(3) C(1) 3.502(3) ? . 1_655
O(3) C(2) 3.380(4) ? . .
O(3) C(7) 3.556(3) ? . .
O(3) C(14) 3.481(4) ? . .
N(1) Cl(1) 3.024(2) ? . 3_656
C(1) Cl(1) 3.536(2) ? . 3_756
C(1) O(3) 3.502(3) ? . 1_455
C(2) O(3) 3.380(4) ? . .
C(2) C(14) 3.506(3) ? . 1_455
C(4) C(7) 3.581(3) ? . 1_455
C(6) C(9) 3.523(2) ? . 1_455
C(7) O(3) 3.556(3) ? . .
C(7) C(4) 3.581(3) ? . 1_655
C(8) C(11) 3.522(3) ? . 1_455
C(9) C(6) 3.523(2) ? . 1_655
C(10) O(2) 3.466(3) ? . 4_455
C(11) C(8) 3.522(3) ? . 1_655
C(14) O(2) 3.570(2) ? . 1_455
C(14) O(3) 3.481(4) ? . .
C(14) C(2) 3.506(3) ? . 1_655
C(14) C(15) 3.595(3) ? . 1_455
C(15) O(1) 3.555(3) ? . 1_554
C(15) O(1) 3.274(4) ? . 1_654
C(15) C(14) 3.595(3) ? . 1_655
Cl(1) H(1) 2.166 ? . 3_656
Cl(1) H(2) 2.986 ? . 1_655
Cl(1) H(2) 3.487 ? . 3_756
Cl(1) H(3) 3.546 ? . 1_655
Cl(1) H(4) 3.476 ? . 1_554
Cl(1) H(5) 2.674 ? . 1_654
Cl(1) H(15) 2.38(5) ? . .
Cl(1) H(15) 3.46(5) ? . 1_655
Cl(1) H(16) 3.53(6) ? . .
Cl(1) H(16) 2.31(5) ? . 1_655
O(1) H(9) 3.471 ? . 4_455
O(1) H(10) 2.967 ? . 1_556
O(1) H(12) 2.781 ? . 1_456
O(1) H(13) 2.986 ? . 1_456
O(1) H(14) 3.598 ? . 1_456
O(1) H(14) 2.654 ? . 1_556
O(2) H(7) 3.260 ? . 4_554
O(2) H(8) 2.755 ? . 4_554
O(2) H(9) 2.975 ? . 4_454
O(3) H(1) 3.569 ? . 3_656
O(3) H(2) 3.163 ? . 1_655
O(3) H(2) 3.410 ? . 3_656
O(3) H(3) 2.469 ? . .
O(3) H(4) 3.114 ? . 1_554
O(3) H(5) 3.340 ? . 1_554
O(3) H(6) 2.632 ? . .
O(3) H(10) 3.366 ? . 1_455
O(3) H(11) 2.561 ? . .
N(1) H(5) 3.581 ? . 3_657
N(1) H(6) 3.460 ? . 1_455
N(1) H(15) 3.48(4) ? . 3_656
C(1) H(6) 3.396 ? . 1_455
C(1) H(15) 3.35(3) ? . 1_455
C(1) H(16) 3.59(4) ? . 3_656
C(2) H(1) 3.593 ? . 1_655
C(2) H(6) 3.494 ? . 1_455
C(2) H(11) 3.199 ? . 1_455
C(2) H(16) 3.35(5) ? . .
C(4) H(15) 3.46(4) ? . 1_556
C(5) H(16) 3.47(4) ? . 1_556
C(6) H(14) 3.483 ? . 1_556
C(8) H(13) 3.512 ? . 1_556
C(8) H(14) 3.561 ? . 1_556
C(10) H(13) 3.051 ? . 4_455
C(11) H(7) 3.589 ? . 1_655
C(11) H(8) 3.593 ? . 4_454
C(11) H(13) 3.367 ? . 4_455
C(12) H(8) 3.515 ? . 4_454
C(12) H(9) 3.507 ? . 4_454
C(13) H(6) 3.527 ? . 1_655
C(13) H(12) 2.830 ? . 1_455
C(14) H(3) 3.274 ? . 1_655
C(14) H(12) 2.827 ? . 1_455
C(15) H(4) 3.278 ? . 1_654
C(15) H(7) 3.274 ? . 1_554
C(15) H(8) 3.116 ? . 4_554
C(15) H(9) 3.062 ? . 4_454
C(15) H(11) 3.573 ? . 1_655
H(1) Cl(1) 2.166 ? . 3_656
H(1) O(3) 3.569 ? . 3_656
H(1) C(2) 3.593 ? . 1_455
H(1) H(3) 3.542 ? . 1_455
H(1) H(5) 3.442 ? . 3_657
H(1) H(15) 2.925 ? . 3_656
H(1) H(16) 3.438 ? . 3_656
H(2) Cl(1) 2.986 ? . 1_455
H(2) Cl(1) 3.487 ? . 3_756
H(2) O(3) 3.163 ? . 1_455
H(2) O(3) 3.410 ? . 3_656
H(2) H(2) 3.194 ? . 3_556
H(2) H(15) 2.851 ? . 1_455
H(2) H(15) 3.150 ? . 3_656
H(2) H(16) 3.493 ? . .
H(2) H(16) 3.165 ? . 3_656
H(3) Cl(1) 3.546 ? . 1_455
H(3) O(3) 2.469 ? . .
H(3) C(14) 3.274 ? . 1_455
H(3) H(1) 3.542 ? . 1_655
H(3) H(11) 3.045 ? . 1_455
H(3) H(15) 3.166 ? . .
H(3) H(16) 2.491 ? . .
H(4) Cl(1) 3.476 ? . 1_556
H(4) O(3) 3.114 ? . 1_556
H(4) C(15) 3.278 ? . 1_456
H(4) H(12) 2.767 ? . 1_456
H(4) H(13) 3.577 ? . 1_456
H(4) H(14) 3.025 ? . 1_456
H(4) H(15) 2.864 ? . 1_556
H(4) H(16) 3.116 ? . 1_556
H(5) Cl(1) 2.674 ? . 1_456
H(5) O(3) 3.340 ? . 1_556
H(5) N(1) 3.581 ? . 3_657
H(5) H(1) 3.442 ? . 3_657
H(5) H(15) 3.173 ? . 1_556
H(5) H(16) 2.771 ? . 1_556
H(6) O(3) 2.632 ? . .
H(6) N(1) 3.460 ? . 1_655
H(6) C(1) 3.396 ? . 1_655
H(6) C(2) 3.494 ? . 1_655
H(6) C(13) 3.527 ? . 1_455
H(6) H(15) 3.205 ? . .
H(6) H(16) 3.224 ? . .
H(7) O(2) 3.260 ? . 4_455
H(7) C(11) 3.589 ? . 1_455
H(7) C(15) 3.274 ? . 1_556
H(7) H(9) 3.591 ? . 1_455
H(7) H(9) 3.070 ? . 4_455
H(7) H(13) 2.773 ? . 1_556
H(7) H(14) 2.895 ? . 1_556
H(8) O(2) 2.755 ? . 4_455
H(8) C(11) 3.593 ? . 4_555
H(8) C(12) 3.515 ? . 4_555
H(8) C(15) 3.116 ? . 4_455
H(8) H(12) 3.341 ? . 4_455
H(8) H(13) 3.273 ? . 1_556
H(8) H(13) 2.731 ? . 4_455
H(9) O(1) 3.471 ? . 4_554
H(9) O(2) 2.975 ? . 4_555
H(9) C(12) 3.507 ? . 4_555
H(9) C(15) 3.062 ? . 4_555
H(9) H(7) 3.591 ? . 1_655
H(9) H(7) 3.070 ? . 4_554
H(9) H(13) 3.287 ? . 4_455
H(9) H(13) 2.762 ? . 4_555
H(9) H(14) 2.976 ? . 4_555
H(10) O(1) 2.967 ? . 1_554
H(10) O(3) 3.366 ? . 1_655
H(10) H(12) 2.792 ? . 1_455
H(10) H(16) 3.228 ? . 1_655
H(11) O(3) 2.561 ? . .
H(11) C(2) 3.199 ? . 1_655
H(11) C(15) 3.573 ? . 1_455
H(11) H(3) 3.045 ? . 1_655
H(11) H(12) 2.773 ? . 1_455
H(11) H(15) 2.714 ? . .
H(11) H(16) 3.366 ? . .
H(12) O(1) 2.781 ? . 1_654
H(12) C(13) 2.830 ? . 1_655
H(12) C(14) 2.827 ? . 1_655
H(12) H(4) 2.767 ? . 1_654
H(12) H(8) 3.341 ? . 4_554
H(12) H(10) 2.792 ? . 1_655
H(12) H(11) 2.773 ? . 1_655
H(13) O(1) 2.986 ? . 1_654
H(13) C(8) 3.512 ? . 1_554
H(13) C(10) 3.051 ? . 4_554
H(13) C(11) 3.367 ? . 4_554
H(13) H(4) 3.577 ? . 1_654
H(13) H(7) 2.773 ? . 1_554
H(13) H(8) 3.273 ? . 1_554
H(13) H(8) 2.731 ? . 4_554
H(13) H(9) 2.762 ? . 4_454
H(13) H(9) 3.287 ? . 4_554
H(14) O(1) 2.654 ? . 1_554
H(14) O(1) 3.598 ? . 1_654
H(14) C(6) 3.483 ? . 1_554
H(14) C(8) 3.561 ? . 1_554
H(14) H(4) 3.025 ? . 1_654
H(14) H(7) 2.895 ? . 1_554
H(14) H(9) 2.976 ? . 4_454
H(15) Cl(1) 3.46(5) ? . 1_455
H(15) Cl(1) 2.38(5) ? . .
H(15) N(1) 3.48(4) ? . 3_656
H(15) C(1) 3.35(3) ? . 1_655
H(15) C(4) 3.46(4) ? . 1_554
H(15) H(1) 2.925 ? . 3_656
H(15) H(2) 2.851 ? . 1_655
H(15) H(2) 3.150 ? . 3_656
H(15) H(3) 3.166 ? . .
H(15) H(4) 2.864 ? . 1_554
H(15) H(5) 3.173 ? . 1_554
H(15) H(6) 3.205 ? . .
H(15) H(11) 2.714 ? . .
H(16) Cl(1) 2.31(5) ? . 1_455
H(16) Cl(1) 3.53(6) ? . .
H(16) C(1) 3.59(4) ? . 3_656
H(16) C(2) 3.35(5) ? . .
H(16) C(5) 3.47(4) ? . 1_554
H(16) H(1) 3.438 ? . 3_656
H(16) H(2) 3.493 ? . .
H(16) H(2) 3.165 ? . 3_656
H(16) H(3) 2.491 ? . .
H(16) H(4) 3.116 ? . 1_554
H(16) H(5) 2.771 ? . 1_554
H(16) H(6) 3.224 ? . .
H(16) H(10) 3.228 ? . 1_455
H(16) H(11) 3.366 ? . .


#==============================================================================

# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================

#     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_AC-OEt-HCl-yellow-1
_database_code_depnum_ccdc_archive 'CCDC 1006004'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H16 Cl N O2'
_chemical_formula_moiety         'C16 H16 Cl N O2'
_chemical_formula_weight         289.76
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.12742(15)
_cell_length_b                   12.8781(3)
_cell_length_c                   15.9623(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.4496(14)
_cell_angle_gamma                90.0000
_cell_volume                     1424.95(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4740
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      67.95
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.00
_exptl_absorpt_coefficient_mu    2.379
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15692
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2621
_reflns_number_gt                2312
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1004
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2621
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0495P)²+0.5911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00011(18)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.07225(6) 1.71416(3) 0.46338(3) 0.02879(16) Uani 1.0 4 d . . .
O1 O 0.1378(2) 1.14284(9) 0.36087(8) 0.0340(4) Uani 1.0 4 d . . .
O2 O 0.48525(19) 0.95208(9) 0.87525(7) 0.0294(3) Uani 1.0 4 d . . .
N1 N 0.0891(2) 0.87475(12) 0.13860(9) 0.0277(4) Uani 1.0 4 d . . .
C1 C 0.0754(3) 0.97840(14) 0.13553(11) 0.0303(5) Uani 1.0 4 d . . .
C2 C 0.0991(3) 1.03456(14) 0.21024(11) 0.0275(4) Uani 1.0 4 d . . .
C3 C 0.1397(3) 0.98358(13) 0.28925(11) 0.0233(4) Uani 1.0 4 d . . .
C4 C 0.1500(3) 0.87594(13) 0.29034(11) 0.0251(4) Uani 1.0 4 d . . .
C5 C 0.1238(3) 0.82294(14) 0.21344(11) 0.0281(4) Uani 1.0 4 d . . .
C6 C 0.1672(3) 1.04957(13) 0.36986(11) 0.0253(4) Uani 1.0 4 d . . .
C7 C 0.2320(3) 1.00068(14) 0.45366(11) 0.0271(4) Uani 1.0 4 d . . .
C8 C 0.2397(3) 1.05670(14) 0.52528(11) 0.0269(4) Uani 1.0 4 d . . .
C9 C 0.3021(3) 1.02300(13) 0.61460(11) 0.0248(4) Uani 1.0 4 d . . .
C10 C 0.3027(3) 1.09626(13) 0.68028(11) 0.0249(4) Uani 1.0 4 d . . .
C11 C 0.3651(3) 1.07060(13) 0.76602(11) 0.0259(4) Uani 1.0 4 d . . .
C12 C 0.4270(3) 0.96981(13) 0.78949(11) 0.0243(4) Uani 1.0 4 d . . .
C13 C 0.4276(3) 0.89562(13) 0.72552(11) 0.0262(4) Uani 1.0 4 d . . .
C14 C 0.3652(3) 0.92245(13) 0.63961(11) 0.0267(4) Uani 1.0 4 d . . .
C15 C 0.5432(3) 0.84872(14) 0.90485(11) 0.0289(4) Uani 1.0 4 d . . .
C16 C 0.5880(3) 0.85189(15) 1.00166(11) 0.0319(5) Uani 1.0 4 d . . .
H1 H 0.0749 0.8397 0.0902 0.0332 Uiso 1.0 4 calc R . .
H1A H 0.0492 1.0131 0.0815 0.0363 Uiso 1.0 4 calc R . .
H2 H 0.0879 1.1081 0.2081 0.0330 Uiso 1.0 4 calc R . .
H4 H 0.1750 0.8393 0.3434 0.0301 Uiso 1.0 4 calc R . .
H5 H 0.1303 0.7493 0.2135 0.0337 Uiso 1.0 4 calc R . .
H7 H 0.2687 0.9296 0.4577 0.0326 Uiso 1.0 4 calc R . .
H8 H 0.1994 1.1270 0.5167 0.0323 Uiso 1.0 4 calc R . .
H10 H 0.2591 1.1649 0.6651 0.0299 Uiso 1.0 4 calc R . .
H11 H 0.3659 1.1216 0.8091 0.0310 Uiso 1.0 4 calc R . .
H13 H 0.4707 0.8270 0.7410 0.0314 Uiso 1.0 4 calc R . .
H14 H 0.3653 0.8714 0.5967 0.0320 Uiso 1.0 4 calc R . .
H15A H 0.6585 0.8272 0.8846 0.0347 Uiso 1.0 4 calc R . .
H15B H 0.4378 0.7987 0.8826 0.0347 Uiso 1.0 4 calc R . .
H16A H 0.4687 0.8633 1.0209 0.0383 Uiso 1.0 4 calc R . .
H16B H 0.6786 0.9086 1.0224 0.0383 Uiso 1.0 4 calc R . .
H16C H 0.6460 0.7858 1.0248 0.0383 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C6 1.222(2) yes . .
O2 C12 1.354(2) yes . .
O2 C15 1.440(3) yes . .
N1 C1 1.338(3) yes . .
N1 C5 1.340(3) yes . .
C1 C2 1.371(3) yes . .
C2 C3 1.391(3) yes . .
C3 C4 1.388(3) yes . .
C3 C6 1.516(3) yes . .
C4 C5 1.379(3) yes . .
C6 C7 1.453(3) yes . .
C7 C8 1.342(3) yes . .
C8 C9 1.457(3) yes . .
C9 C10 1.410(3) yes . .
C9 C14 1.398(3) yes . .
C10 C11 1.377(3) yes . .
C11 C12 1.394(3) yes . .
C12 C13 1.399(3) yes . .
C13 C14 1.383(3) yes . .
C15 C16 1.504(3) yes . .
N1 H1 0.880 no . .
C1 H1A 0.950 no . .
C2 H2 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16A 0.980 no . .
C16 H16B 0.980 no . .
C16 H16C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C12 O2 C15 118.98(13) yes . . .
C1 N1 C5 121.73(16) yes . . .
N1 C1 C2 120.07(16) yes . . .
C1 C2 C3 119.81(17) yes . . .
C2 C3 C4 118.81(16) yes . . .
C2 C3 C6 117.61(15) yes . . .
C4 C3 C6 123.58(16) yes . . .
C3 C4 C5 119.17(16) yes . . .
N1 C5 C4 120.39(17) yes . . .
O1 C6 C3 117.81(15) yes . . .
O1 C6 C7 122.89(16) yes . . .
C3 C6 C7 119.28(15) yes . . .
C6 C7 C8 119.50(17) yes . . .
C7 C8 C9 128.02(17) yes . . .
C8 C9 C10 118.40(15) yes . . .
C8 C9 C14 124.05(16) yes . . .
C10 C9 C14 117.54(16) yes . . .
C9 C10 C11 121.53(16) yes . . .
C10 C11 C12 119.96(16) yes . . .
O2 C12 C11 115.61(15) yes . . .
O2 C12 C13 124.77(15) yes . . .
C11 C12 C13 119.62(16) yes . . .
C12 C13 C14 119.87(16) yes . . .
C9 C14 C13 121.48(16) yes . . .
O2 C15 C16 106.75(15) yes . . .
C1 N1 H1 119.140 no . . .
C5 N1 H1 119.130 no . . .
N1 C1 H1A 119.963 no . . .
C2 C1 H1A 119.970 no . . .
C1 C2 H2 120.087 no . . .
C3 C2 H2 120.103 no . . .
C3 C4 H4 120.410 no . . .
C5 C4 H4 120.418 no . . .
N1 C5 H5 119.802 no . . .
C4 C5 H5 119.809 no . . .
C6 C7 H7 120.251 no . . .
C8 C7 H7 120.248 no . . .
C7 C8 H8 115.991 no . . .
C9 C8 H8 115.991 no . . .
C9 C10 H10 119.237 no . . .
C11 C10 H10 119.236 no . . .
C10 C11 H11 120.023 no . . .
C12 C11 H11 120.020 no . . .
C12 C13 H13 120.061 no . . .
C14 C13 H13 120.067 no . . .
C9 C14 H14 119.264 no . . .
C13 C14 H14 119.258 no . . .
O2 C15 H15A 110.370 no . . .
O2 C15 H15B 110.369 no . . .
C16 C15 H15A 110.373 no . . .
C16 C15 H15B 110.373 no . . .
H15A C15 H15B 108.606 no . . .
C15 C16 H16A 109.474 no . . .
C15 C16 H16B 109.468 no . . .
C15 C16 H16C 109.471 no . . .
H16A C16 H16B 109.473 no . . .
H16A C16 H16C 109.472 no . . .
H16B C16 H16C 109.470 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C12 O2 C15 C16 -176.70(14) no . . . .
C15 O2 C12 C11 177.25(14) no . . . .
C15 O2 C12 C13 -3.5(3) no . . . .
C1 N1 C5 C4 -1.2(3) no . . . .
C5 N1 C1 C2 0.7(3) no . . . .
N1 C1 C2 C3 0.7(3) no . . . .
C1 C2 C3 C4 -1.7(3) no . . . .
C1 C2 C3 C6 179.19(15) no . . . .
C2 C3 C4 C5 1.3(3) no . . . .
C2 C3 C6 O1 5.4(3) no . . . .
C2 C3 C6 C7 -172.78(15) no . . . .
C4 C3 C6 O1 -173.60(16) no . . . .
C4 C3 C6 C7 8.2(3) no . . . .
C6 C3 C4 C5 -179.70(14) no . . . .
C3 C4 C5 N1 0.1(3) no . . . .
O1 C6 C7 C8 7.9(3) no . . . .
C3 C6 C7 C8 -173.94(15) no . . . .
C6 C7 C8 C9 -179.20(16) no . . . .
C7 C8 C9 C10 178.50(18) no . . . .
C7 C8 C9 C14 -0.3(3) no . . . .
C8 C9 C10 C11 -178.13(15) no . . . .
C8 C9 C14 C13 178.30(16) no . . . .
C10 C9 C14 C13 -0.5(3) no . . . .
C14 C9 C10 C11 0.7(3) no . . . .
C9 C10 C11 C12 -0.9(3) no . . . .
C10 C11 C12 O2 -179.90(16) no . . . .
C10 C11 C12 C13 0.8(3) no . . . .
O2 C12 C13 C14 -179.80(15) no . . . .
C11 C12 C13 C14 -0.6(3) no . . . .
C12 C13 C14 C9 0.4(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C2 2.737(3) no . .
O1 C8 2.785(2) no . .
O2 C10 3.598(2) no . .
N1 C3 2.734(3) no . .
C1 C4 2.742(3) no . .
C2 C5 2.731(3) no . .
C4 C7 3.002(3) no . .
C7 C14 3.069(3) no . .
C9 C12 2.810(3) no . .
C10 C13 2.773(3) no . .
C11 C14 2.777(3) no . .
C13 C15 2.853(3) no . .
Cl1 N1 2.9987(16) no . 4_575
Cl1 C1 3.4706(18) no . 2_555
Cl1 C2 3.5982(18) no . 2_555
O1 N1 3.397(2) no . 2_555
O1 C5 3.039(3) no . 2_555
O2 C1 3.300(3) no . 3_676
O2 C2 3.542(3) no . 3_676
O2 C16 3.314(3) no . 3_677
N1 Cl1 2.9987(16) no . 4_574
N1 O1 3.397(2) no . 2_545
C1 Cl1 3.4706(18) no . 2_545
C1 O2 3.300(3) no . 3_676
C1 C12 3.533(3) no . 3_676
C2 Cl1 3.5982(18) no . 2_545
C2 O2 3.542(3) no . 3_676
C2 C12 3.377(3) no . 3_676
C2 C13 3.411(3) no . 3_676
C3 C10 3.456(3) no . 3_576
C3 C11 3.568(3) no . 3_576
C3 C13 3.511(3) no . 3_676
C4 C10 3.386(3) no . 3_576
C5 O1 3.039(3) no . 2_545
C5 C13 3.529(3) no . 4_564
C6 C9 3.537(3) no . 3_576
C6 C14 3.390(3) no . 3_676
C7 C8 3.533(3) no . 3_576
C8 C7 3.533(3) no . 3_576
C9 C6 3.537(3) no . 3_576
C10 C3 3.456(3) no . 3_576
C10 C4 3.386(3) no . 3_576
C11 C3 3.568(3) no . 3_576
C12 C1 3.533(3) no . 3_676
C12 C2 3.377(3) no . 3_676
C13 C2 3.411(3) no . 3_676
C13 C3 3.511(3) no . 3_676
C13 C5 3.529(3) no . 4_565
C14 C6 3.390(3) no . 3_676
C16 O2 3.314(3) no . 3_677
O1 H2 2.4236 no . .
O1 H7 3.1827 no . .
O1 H8 2.4316 no . .
O2 H11 2.4866 no . .
O2 H13 2.6632 no . .
O2 H16A 2.6176 no . .
O2 H16B 2.4948 no . .
O2 H16C 3.2128 no . .
N1 H2 3.2034 no . .
N1 H4 3.2158 no . .
C1 H5 3.1911 no . .
C2 H1 3.1375 no . .
C2 H4 3.2563 no . .
C3 H1A 3.2495 no . .
C3 H5 3.2457 no . .
C3 H7 2.7221 no . .
C4 H1 3.1486 no . .
C4 H2 3.2538 no . .
C4 H7 2.6981 no . .
C5 H1A 3.1925 no . .
C6 H2 2.6228 no . .
C6 H4 2.7438 no . .
C6 H8 2.5080 no . .
C7 H4 2.6927 no . .
C7 H14 2.8062 no . .
C8 H10 2.6068 no . .
C8 H14 2.7054 no . .
C9 H7 2.7380 no . .
C9 H11 3.2869 no . .
C9 H13 3.2808 no . .
C10 H8 2.5736 no . .
C10 H14 3.2623 no . .
C11 H13 3.2726 no . .
C12 H10 3.2535 no . .
C12 H14 3.2626 no . .
C12 H15A 2.6901 no . .
C12 H15B 2.6490 no . .
C13 H11 3.2732 no . .
C13 H15A 2.8270 no . .
C13 H15B 2.7868 no . .
C14 H7 2.8253 no . .
C14 H8 3.3328 no . .
C14 H10 3.2605 no . .
C15 H13 2.5600 no . .
H1 H1A 2.2421 no . .
H1 H5 2.2414 no . .
H1A H2 2.3220 no . .
H4 H5 2.3320 no . .
H4 H7 2.1358 no . .
H7 H8 2.7944 no . .
H7 H14 2.2898 no . .
H8 H10 2.3577 no . .
H10 H11 2.3167 no . .
H13 H14 2.3237 no . .
H13 H15A 2.3702 no . .
H13 H15B 2.3539 no . .
H15A H16A 2.8539 no . .
H15A H16B 2.4100 no . .
H15A H16C 2.3211 no . .
H15B H16A 2.3209 no . .
H15B H16B 2.8538 no . .
H15B H16C 2.4104 no . .
Cl1 H1 2.1359 no . 4_575
Cl1 H1A 2.7712 no . 2_555
Cl1 H1A 3.5061 no . 4_575
Cl1 H2 3.0339 no . 2_555
Cl1 H4 2.7294 no . 1_565
Cl1 H7 3.1183 no . 1_565
Cl1 H8 2.8846 no . 3_586
Cl1 H10 3.1546 no . 3_586
Cl1 H14 3.3048 no . 1_565
Cl1 H15A 2.9725 no . 4_474
Cl1 H15B 3.1688 no . 4_574
Cl1 H16A 2.9357 no . 4_574
Cl1 H16B 3.5338 no . 4_474
Cl1 H16C 3.4023 no . 4_474
O1 H1 3.1444 no . 2_555
O1 H5 2.4259 no . 2_555
O1 H13 3.5629 no . 3_676
O1 H14 3.4522 no . 3_676
O1 H16C 2.7906 no . 2_656
O2 H1A 3.2594 no . 3_676
O2 H16A 2.8727 no . 3_677
O2 H16B 2.8531 no . 3_677
N1 H11 3.5315 no . 3_576
N1 H16B 3.1088 no . 1_454
N1 H16C 3.4523 no . 1_454
C1 H1A 3.3725 no . 3_575
C1 H15A 3.2021 no . 3_676
C1 H16B 3.1129 no . 1_454
C2 H5 3.5674 no . 2_555
C2 H13 3.4753 no . 3_676
C2 H15A 3.1089 no . 3_676
C4 H10 3.2019 no . 3_576
C4 H15B 3.1672 no . 4_564
C5 H2 3.5189 no . 2_545
C5 H11 3.4980 no . 3_576
C5 H13 3.0867 no . 4_564
C5 H15B 3.4564 no . 4_564
C6 H5 3.4010 no . 2_555
C6 H14 3.4055 no . 3_676
C6 H16C 3.5798 no . 2_656
C7 H14 3.5595 no . 3_676
C8 H7 3.4560 no . 3_676
C8 H16C 3.2108 no . 2_656
C9 H7 3.5649 no . 3_676
C10 H4 3.4386 no . 3_576
C10 H13 3.4740 no . 2_656
C10 H15A 3.1826 no . 2_656
C10 H15B 3.4771 no . 2_656
C11 H13 3.5134 no . 2_656
C11 H16A 3.4382 no . 3_677
C11 H16B 3.4733 no . 3_677
C12 H2 3.5918 no . 3_676
C12 H5 3.5648 no . 4_565
C13 H2 3.3690 no . 3_676
C13 H5 2.7960 no . 4_565
C14 H5 3.1627 no . 4_565
C15 H1A 3.3709 no . 3_676
C15 H2 3.5606 no . 3_676
C15 H4 3.5371 no . 4_565
C15 H8 3.4667 no . 2_646
C15 H10 3.0930 no . 2_646
C16 H1 3.4327 no . 1_656
C16 H8 3.3127 no . 2_646
C16 H11 2.9806 no . 3_677
C16 H16B 3.5963 no . 3_677
H1 Cl1 2.1359 no . 4_574
H1 O1 3.1444 no . 2_545
H1 C16 3.4327 no . 1_454
H1 H1A 3.2808 no . 3_575
H1 H8 3.5616 no . 2_545
H1 H14 3.4039 no . 4_564
H1 H16A 3.2620 no . 1_554
H1 H16B 2.9180 no . 1_454
H1 H16C 3.0715 no . 1_454
H1A Cl1 2.7712 no . 2_545
H1A Cl1 3.5061 no . 4_574
H1A O2 3.2594 no . 3_676
H1A C1 3.3725 no . 3_575
H1A C15 3.3709 no . 3_676
H1A H1 3.2808 no . 3_575
H1A H1A 2.5556 no . 3_575
H1A H15A 2.8878 no . 3_676
H1A H16B 2.9185 no . 1_454
H1A H16B 3.0050 no . 3_676
H2 Cl1 3.0339 no . 2_545
H2 C5 3.5189 no . 2_555
H2 C12 3.5918 no . 3_676
H2 C13 3.3690 no . 3_676
H2 C15 3.5606 no . 3_676
H2 H4 3.5117 no . 2_555
H2 H5 2.8633 no . 2_555
H2 H10 3.3009 no . 4_574
H2 H13 3.1733 no . 3_676
H2 H15A 2.7196 no . 3_676
H4 Cl1 2.7294 no . 1_545
H4 C10 3.4386 no . 3_576
H4 C15 3.5371 no . 4_564
H4 H2 3.5117 no . 2_545
H4 H10 3.0653 no . 3_576
H4 H15B 2.5522 no . 4_564
H5 O1 2.4259 no . 2_545
H5 C2 3.5674 no . 2_545
H5 C6 3.4010 no . 2_545
H5 C12 3.5648 no . 4_564
H5 C13 2.7960 no . 4_564
H5 C14 3.1627 no . 4_564
H5 H2 2.8633 no . 2_545
H5 H13 2.5586 no . 4_564
H5 H14 3.1862 no . 4_564
H5 H15B 3.1180 no . 4_564
H7 Cl1 3.1183 no . 1_545
H7 C8 3.4560 no . 3_676
H7 C9 3.5649 no . 3_676
H7 H8 3.5302 no . 3_576
H7 H15B 3.4941 no . 4_564
H8 Cl1 2.8846 no . 3_586
H8 C15 3.4667 no . 2_656
H8 C16 3.3127 no . 2_656
H8 H1 3.5616 no . 2_555
H8 H7 3.5302 no . 3_576
H8 H15A 3.0677 no . 2_656
H8 H15B 3.4963 no . 2_656
H8 H16C 2.4844 no . 2_656
H10 Cl1 3.1546 no . 3_586
H10 C4 3.2019 no . 3_576
H10 C15 3.0930 no . 2_656
H10 H2 3.3009 no . 4_575
H10 H4 3.0653 no . 3_576
H10 H13 2.9947 no . 2_656
H10 H15A 2.3577 no . 2_656
H10 H15B 2.9967 no . 2_656
H11 N1 3.5315 no . 3_576
H11 C5 3.4980 no . 3_576
H11 C16 2.9806 no . 3_677
H11 H13 3.0707 no . 2_656
H11 H16A 2.7018 no . 3_677
H11 H16B 2.8070 no . 3_677
H11 H16C 2.9265 no . 3_677
H13 O1 3.5629 no . 3_676
H13 C2 3.4753 no . 3_676
H13 C5 3.0867 no . 4_565
H13 C10 3.4740 no . 2_646
H13 C11 3.5134 no . 2_646
H13 H2 3.1733 no . 3_676
H13 H5 2.5586 no . 4_565
H13 H10 2.9947 no . 2_646
H13 H11 3.0707 no . 2_646
H14 Cl1 3.3048 no . 1_545
H14 O1 3.4522 no . 3_676
H14 C6 3.4055 no . 3_676
H14 C7 3.5595 no . 3_676
H14 H1 3.4039 no . 4_565
H14 H5 3.1862 no . 4_565
H14 H16A 3.4001 no . 4_564
H14 H16C 3.2381 no . 4_564
H15A Cl1 2.9725 no . 4_675
H15A C1 3.2021 no . 3_676
H15A C2 3.1089 no . 3_676
H15A C10 3.1826 no . 2_646
H15A H1A 2.8878 no . 3_676
H15A H2 2.7196 no . 3_676
H15A H8 3.0677 no . 2_646
H15A H10 2.3577 no . 2_646
H15B Cl1 3.1688 no . 4_575
H15B C4 3.1672 no . 4_565
H15B C5 3.4564 no . 4_565
H15B C10 3.4771 no . 2_646
H15B H4 2.5522 no . 4_565
H15B H5 3.1180 no . 4_565
H15B H7 3.4941 no . 4_565
H15B H8 3.4963 no . 2_646
H15B H10 2.9967 no . 2_646
H16A Cl1 2.9357 no . 4_575
H16A O2 2.8727 no . 3_677
H16A C11 3.4382 no . 3_677
H16A H1 3.2620 no . 1_556
H16A H11 2.7018 no . 3_677
H16A H14 3.4001 no . 4_565
H16A H16B 3.1414 no . 3_677
H16B Cl1 3.5338 no . 4_675
H16B O2 2.8531 no . 3_677
H16B N1 3.1088 no . 1_656
H16B C1 3.1129 no . 1_656
H16B C11 3.4733 no . 3_677
H16B C16 3.5963 no . 3_677
H16B H1 2.9180 no . 1_656
H16B H1A 2.9185 no . 1_656
H16B H1A 3.0050 no . 3_676
H16B H11 2.8070 no . 3_677
H16B H16A 3.1414 no . 3_677
H16B H16B 3.4190 no . 3_677
H16C Cl1 3.4023 no . 4_675
H16C O1 2.7906 no . 2_646
H16C N1 3.4523 no . 1_656
H16C C6 3.5798 no . 2_646
H16C C8 3.2108 no . 2_646
H16C H1 3.0715 no . 1_656
H16C H8 2.4844 no . 2_646
H16C H11 2.9265 no . 3_677
H16C H14 3.2381 no . 4_565

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Cl1 . . 4_574 2.9987(16) 0.880 2.136 166.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     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_AC-OEt-HCl-red-1
_database_code_depnum_ccdc_archive 'CCDC 1006005'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H18 Cl N O3'
_chemical_formula_moiety         'C16 H18 Cl N O3'
_chemical_formula_weight         307.78
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.88516(18)
_cell_length_b                   8.6653(3)
_cell_length_c                   18.6176(7)
_cell_angle_alpha                86.980(3)
_cell_angle_beta                 85.549(3)
_cell_angle_gamma                80.147(2)
_cell_volume                     773.52(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3575
_cell_measurement_theta_min      4.77
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324.00
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8223
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2764
_reflns_number_gt                1818
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     198
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0514P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -1.07514(15) 1.25697(7) 0.44523(3) 0.0397(3) Uani 1.0 2 d . . .
O1 O 0.0611(5) 0.9808(2) 0.22593(10) 0.0443(6) Uani 1.0 2 d . . .
O2 O 1.4513(4) 0.33179(18) 0.08216(9) 0.0344(5) Uani 1.0 2 d . . .
O3 O -1.5786(6) 1.3747(3) 0.34656(13) 0.0553(7) Uani 1.0 2 d . . .
N1 N -0.4995(5) 0.8031(3) 0.43347(11) 0.0344(6) Uani 1.0 2 d . . .
C1 C -0.5086(7) 0.9423(3) 0.39749(14) 0.0364(7) Uani 1.0 2 d . . .
C2 C -0.3154(6) 0.9587(3) 0.34224(14) 0.0334(7) Uani 1.0 2 d . . .
C3 C -0.1069(6) 0.8322(3) 0.32356(13) 0.0293(7) Uani 1.0 2 d . . .
C4 C -0.1046(6) 0.6908(3) 0.36350(13) 0.0329(7) Uani 1.0 2 d . . .
C5 C -0.3014(6) 0.6796(3) 0.41847(14) 0.0338(7) Uani 1.0 2 d . . .
C6 C 0.0977(6) 0.8552(3) 0.26015(13) 0.0313(7) Uani 1.0 2 d . . .
C7 C 0.3287(6) 0.7292(3) 0.24358(13) 0.0293(7) Uani 1.0 2 d . . .
C8 C 0.4993(6) 0.7393(3) 0.18438(13) 0.0296(7) Uani 1.0 2 d . . .
C9 C 0.7451(6) 0.6292(3) 0.16090(13) 0.0281(7) Uani 1.0 2 d . . .
C10 C 0.8919(6) 0.6593(3) 0.09561(13) 0.0312(7) Uani 1.0 2 d . . .
C11 C 1.1279(6) 0.5608(3) 0.07141(13) 0.0297(7) Uani 1.0 2 d . . .
C12 C 1.2225(6) 0.4245(3) 0.11200(13) 0.0285(6) Uani 1.0 2 d . . .
C13 C 1.0820(6) 0.3919(3) 0.17729(13) 0.0314(7) Uani 1.0 2 d . . .
C14 C 0.8459(6) 0.4935(3) 0.20105(13) 0.0301(7) Uani 1.0 2 d . . .
C15 C 1.5619(6) 0.1883(3) 0.12035(14) 0.0341(7) Uani 1.0 2 d . . .
C16 C 1.7991(6) 0.1087(3) 0.07218(14) 0.0388(8) Uani 1.0 2 d . . .
H1 H -0.6287 0.7927 0.4682 0.0413 Uiso 1.0 2 calc R . .
H1A H -0.6487 1.0284 0.4105 0.0437 Uiso 1.0 2 calc R . .
H2 H -0.3218 1.0564 0.3162 0.0400 Uiso 1.0 2 calc R . .
H3 H -1.394(11) 1.330(6) 0.377(3) 0.142(18) Uiso 1.0 2 d . . .
H4 H 0.0341 0.6028 0.3523 0.0394 Uiso 1.0 2 calc R . .
H5 H -0.2984 0.5842 0.4462 0.0406 Uiso 1.0 2 calc R . .
H6 H -1.706(10) 1.342(5) 0.376(3) 0.103(17) Uiso 1.0 2 d . . .
H7 H 0.3584 0.6390 0.2751 0.0352 Uiso 1.0 2 calc R . .
H8 H 0.4542 0.8299 0.1538 0.0355 Uiso 1.0 2 calc R . .
H10 H 0.8265 0.7506 0.0672 0.0375 Uiso 1.0 2 calc R . .
H11 H 1.2262 0.5850 0.0274 0.0356 Uiso 1.0 2 calc R . .
H13 H 1.1476 0.3004 0.2055 0.0377 Uiso 1.0 2 calc R . .
H14 H 0.7503 0.4704 0.2457 0.0361 Uiso 1.0 2 calc R . .
H15A H 1.4175 0.1210 0.1299 0.0409 Uiso 1.0 2 calc R . .
H15B H 1.6285 0.2111 0.1669 0.0409 Uiso 1.0 2 calc R . .
H16A H 1.8841 0.0104 0.0959 0.0466 Uiso 1.0 2 calc R . .
H16B H 1.9387 0.1774 0.0627 0.0466 Uiso 1.0 2 calc R . .
H16C H 1.7294 0.0862 0.0266 0.0466 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C6 1.224(3) yes . .
O2 C12 1.359(3) yes . .
O2 C15 1.442(3) yes . .
N1 C1 1.344(4) yes . .
N1 C5 1.340(3) yes . .
C1 C2 1.360(4) yes . .
C2 C3 1.401(4) yes . .
C3 C4 1.398(4) yes . .
C3 C6 1.514(4) yes . .
C4 C5 1.360(4) yes . .
C6 C7 1.456(4) yes . .
C7 C8 1.338(4) yes . .
C8 C9 1.453(4) yes . .
C9 C10 1.398(4) yes . .
C9 C14 1.397(4) yes . .
C10 C11 1.373(4) yes . .
C11 C12 1.397(4) yes . .
C12 C13 1.389(4) yes . .
C13 C14 1.384(4) yes . .
C15 C16 1.501(4) yes . .
O3 H3 1.10(5) no . .
O3 H6 0.86(5) no . .
N1 H1 0.880 no . .
C1 H1A 0.950 no . .
C2 H2 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15A 0.990 no . .
C15 H15B 0.990 no . .
C16 H16A 0.980 no . .
C16 H16B 0.980 no . .
C16 H16C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C12 O2 C15 118.69(19) yes . . .
C1 N1 C5 122.5(3) yes . . .
N1 C1 C2 119.4(3) yes . . .
C1 C2 C3 120.3(3) yes . . .
C2 C3 C4 117.9(3) yes . . .
C2 C3 C6 118.2(2) yes . . .
C4 C3 C6 123.9(2) yes . . .
C3 C4 C5 119.8(3) yes . . .
N1 C5 C4 120.0(3) yes . . .
O1 C6 C3 117.7(3) yes . . .
O1 C6 C7 123.4(3) yes . . .
C3 C6 C7 118.8(2) yes . . .
C6 C7 C8 120.6(3) yes . . .
C7 C8 C9 128.2(3) yes . . .
C8 C9 C10 119.4(2) yes . . .
C8 C9 C14 123.0(3) yes . . .
C10 C9 C14 117.6(3) yes . . .
C9 C10 C11 121.9(3) yes . . .
C10 C11 C12 119.5(3) yes . . .
O2 C12 C11 115.1(2) yes . . .
O2 C12 C13 125.0(2) yes . . .
C11 C12 C13 119.9(3) yes . . .
C12 C13 C14 119.6(3) yes . . .
C9 C14 C13 121.5(3) yes . . .
O2 C15 C16 106.0(2) yes . . .
H3 O3 H6 100(4) no . . .
C1 N1 H1 118.738 no . . .
C5 N1 H1 118.738 no . . .
N1 C1 H1A 120.329 no . . .
C2 C1 H1A 120.311 no . . .
C1 C2 H2 119.840 no . . .
C3 C2 H2 119.851 no . . .
C3 C4 H4 120.078 no . . .
C5 C4 H4 120.074 no . . .
N1 C5 H5 120.012 no . . .
C4 C5 H5 120.009 no . . .
C6 C7 H7 119.695 no . . .
C8 C7 H7 119.701 no . . .
C7 C8 H8 115.876 no . . .
C9 C8 H8 115.876 no . . .
C9 C10 H10 119.074 no . . .
C11 C10 H10 119.076 no . . .
C10 C11 H11 120.226 no . . .
C12 C11 H11 120.233 no . . .
C12 C13 H13 120.189 no . . .
C14 C13 H13 120.191 no . . .
C9 C14 H14 119.264 no . . .
C13 C14 H14 119.258 no . . .
O2 C15 H15A 110.537 no . . .
O2 C15 H15B 110.541 no . . .
C16 C15 H15A 110.534 no . . .
C16 C15 H15B 110.542 no . . .
H15A C15 H15B 108.709 no . . .
C15 C16 H16A 109.471 no . . .
C15 C16 H16B 109.473 no . . .
C15 C16 H16C 109.474 no . . .
H16A C16 H16B 109.473 no . . .
H16A C16 H16C 109.470 no . . .
H16B C16 H16C 109.468 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C12 O2 C15 C16 176.6(2) no . . . .
C15 O2 C12 C11 -179.7(2) no . . . .
C15 O2 C12 C13 -0.4(4) no . . . .
C1 N1 C5 C4 -2.2(4) no . . . .
C5 N1 C1 C2 2.0(4) no . . . .
N1 C1 C2 C3 -0.7(5) no . . . .
C1 C2 C3 C4 -0.2(4) no . . . .
C1 C2 C3 C6 178.1(3) no . . . .
C2 C3 C4 C5 0.1(4) no . . . .
C2 C3 C6 O1 -3.9(4) no . . . .
C2 C3 C6 C7 175.2(3) no . . . .
C4 C3 C6 O1 174.3(3) no . . . .
C4 C3 C6 C7 -6.5(4) no . . . .
C6 C3 C4 C5 -178.2(3) no . . . .
C3 C4 C5 N1 1.1(5) no . . . .
O1 C6 C7 C8 -6.9(5) no . . . .
C3 C6 C7 C8 174.0(3) no . . . .
C6 C7 C8 C9 177.2(3) no . . . .
C7 C8 C9 C10 178.1(3) no . . . .
C7 C8 C9 C14 -2.6(5) no . . . .
C8 C9 C10 C11 178.9(3) no . . . .
C8 C9 C14 C13 -179.5(3) no . . . .
C10 C9 C14 C13 -0.1(4) no . . . .
C14 C9 C10 C11 -0.4(4) no . . . .
C9 C10 C11 C12 1.4(4) no . . . .
C10 C11 C12 O2 177.6(3) no . . . .
C10 C11 C12 C13 -1.7(4) no . . . .
O2 C12 C13 C14 -178.1(3) no . . . .
C11 C12 C13 C14 1.2(4) no . . . .
C12 C13 C14 C9 -0.2(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C2 2.751(4) no . .
O1 C8 2.818(3) no . .
O2 C10 3.592(3) no . .
N1 C3 2.726(4) no . .
C1 C4 2.743(4) no . .
C2 C5 2.732(4) no . .
C4 C7 3.001(4) no . .
C7 C14 3.046(4) no . .
C9 C12 2.800(4) no . .
C10 C13 2.767(4) no . .
C11 C14 2.770(4) no . .
C13 C15 2.851(4) no . .
Cl1 O3 3.179(3) no . .
Cl1 O3 3.203(3) no . 1_655
Cl1 N1 3.034(3) no . 2_376
Cl1 C5 3.368(3) no . 2_476
O1 C15 3.452(4) no . 1_365
O1 C16 3.288(4) no . 1_365
O2 C9 3.584(4) no . 1_655
O2 C11 3.568(3) no . 2_865
O2 C14 3.535(4) no . 1_655
O3 Cl1 3.203(3) no . 1_455
O3 Cl1 3.179(3) no . .
O3 C4 3.430(4) no . 1_365
O3 C5 3.534(4) no . 1_465
O3 C7 3.515(4) no . 1_365
O3 C14 3.502(4) no . 1_365
N1 Cl1 3.034(3) no . 2_376
C1 C6 3.503(4) no . 1_455
C2 C7 3.524(4) no . 1_455
C3 C7 3.498(4) no . 1_455
C3 C8 3.548(4) no . 1_455
C4 O3 3.430(4) no . 1_745
C4 C14 3.596(4) no . 1_455
C5 Cl1 3.368(3) no . 2_476
C5 O3 3.534(4) no . 1_645
C6 C1 3.503(4) no . 1_655
C6 C9 3.500(4) no . 1_455
C7 O3 3.515(4) no . 1_745
C7 C2 3.524(4) no . 1_655
C7 C3 3.498(4) no . 1_655
C7 C9 3.594(4) no . 1_455
C7 C14 3.531(4) no . 1_455
C8 C3 3.548(4) no . 1_655
C8 C11 3.465(4) no . 1_455
C9 O2 3.584(4) no . 1_455
C9 C6 3.500(4) no . 1_655
C9 C7 3.594(4) no . 1_655
C9 C12 3.546(4) no . 1_455
C11 O2 3.568(3) no . 2_865
C11 C8 3.465(4) no . 1_655
C11 C11 3.317(4) no . 2_765
C12 C9 3.546(4) no . 1_655
C13 C15 3.583(5) no . 1_455
C14 O2 3.535(4) no . 1_455
C14 O3 3.502(4) no . 1_745
C14 C4 3.596(4) no . 1_655
C14 C7 3.531(4) no . 1_655
C15 O1 3.452(4) no . 1_745
C15 C13 3.583(5) no . 1_655
C16 O1 3.288(4) no . 1_745
O1 H2 2.4415 no . .
O1 H7 3.1884 no . .
O1 H8 2.4748 no . .
O2 H11 2.4855 no . .
O2 H13 2.6626 no . .
O2 H16A 3.2074 no . .
O2 H16B 2.5336 no . .
O2 H16C 2.5436 no . .
N1 H2 3.1923 no . .
N1 H4 3.1953 no . .
C1 H5 3.2041 no . .
C2 H1 3.1229 no . .
C2 H4 3.2630 no . .
C3 H1A 3.2561 no . .
C3 H5 3.2479 no . .
C3 H7 2.7061 no . .
C4 H1 3.1252 no . .
C4 H2 3.2613 no . .
C4 H7 2.6793 no . .
C5 H1A 3.2055 no . .
C6 H2 2.6389 no . .
C6 H4 2.7527 no . .
C6 H8 2.5260 no . .
C7 H4 2.6868 no . .
C7 H14 2.7740 no . .
C8 H10 2.6101 no . .
C8 H14 2.6818 no . .
C9 H7 2.7271 no . .
C9 H11 3.2767 no . .
C9 H13 3.2807 no . .
C10 H8 2.5804 no . .
C10 H14 3.2509 no . .
C11 H13 3.2711 no . .
C12 H10 3.2483 no . .
C12 H14 3.2513 no . .
C12 H15A 2.6523 no . .
C12 H15B 2.6948 no . .
C13 H11 3.2701 no . .
C13 H15A 2.7660 no . .
C13 H15B 2.8533 no . .
C14 H7 2.7943 no . .
C14 H8 3.3189 no . .
C14 H10 3.2495 no . .
C15 H13 2.5580 no . .
H1 H1A 2.2477 no . .
H1 H5 2.2391 no . .
H1A H2 2.3120 no . .
H4 H5 2.3113 no . .
H4 H7 2.1075 no . .
H7 H8 2.7862 no . .
H7 H14 2.2503 no . .
H8 H10 2.3693 no . .
H10 H11 2.3129 no . .
H13 H14 2.3261 no . .
H13 H15A 2.3181 no . .
H13 H15B 2.4100 no . .
H15A H16A 2.3685 no . .
H15A H16B 2.8561 no . .
H15A H16C 2.3591 no . .
H15B H16A 2.3613 no . .
H15B H16B 2.3664 no . .
H15B H16C 2.8560 no . .
Cl1 H1 2.1573 no . 2_376
Cl1 H1A 2.6819 no . .
Cl1 H2 3.4423 no . 1_455
Cl1 H3 2.08(5) no . .
Cl1 H4 3.4811 no . 1_465
Cl1 H5 2.8589 no . 1_465
Cl1 H5 3.3216 no . 2_476
Cl1 H6 3.38(5) no . .
Cl1 H6 2.34(5) no . 1_655
O1 H13 2.8739 no . 1_465
O1 H15A 2.7778 no . 1_465
O1 H15B 2.8881 no . 1_365
O1 H16A 2.6192 no . 1_365
O1 H16B 3.4478 no . 1_365
O2 H10 3.3479 no . 2_765
O2 H11 2.6259 no . 2_865
O2 H16B 3.0869 no . 1_455
O3 H1A 3.2324 no . 1_455
O3 H2 2.8931 no . 1_455
O3 H4 2.4921 no . 1_365
O3 H5 3.1957 no . 1_465
O3 H7 2.5714 no . 1_365
O3 H13 3.1812 no . 1_265
O3 H14 2.5734 no . 1_365
N1 H1A 3.4966 no . 2_476
N1 H4 3.5572 no . 1_455
N1 H7 3.5065 no . 1_455
C1 H3 3.50(5) no . 1_655
C1 H6 3.45(4) no . 1_655
C2 H3 3.27(5) no . 1_655
C2 H6 3.60(4) no . 1_655
C3 H1A 3.5604 no . 1_655
C3 H7 3.5304 no . 1_455
C4 H1 3.4019 no . 1_655
C4 H6 3.31(4) no . 1_745
C4 H7 3.3081 no . 1_455
C4 H14 3.1792 no . 1_455
C5 H3 3.28(5) no . 1_645
C5 H7 3.3164 no . 1_455
C6 H16A 3.4398 no . 1_365
C8 H15A 3.3745 no . 1_465
C8 H16A 3.5196 no . 1_465
C10 H8 3.5949 no . 1_655
C10 H11 3.3454 no . 2_765
C10 H16A 3.0356 no . 1_465
C10 H16B 3.3095 no . 2_865
C11 H8 3.5158 no . 1_655
C11 H11 3.0750 no . 2_765
C11 H11 3.5937 no . 2_865
C11 H16B 3.2804 no . 2_865
C12 H11 3.5369 no . 2_765
C12 H11 3.5854 no . 2_865
C12 H16B 2.9617 no . 1_455
C13 H7 3.3917 no . 1_655
C13 H15B 2.9475 no . 1_455
C13 H16B 3.0975 no . 1_455
C14 H4 3.2631 no . 1_655
C14 H7 3.3993 no . 1_655
C14 H15B 2.9464 no . 1_455
C15 H8 3.2580 no . 1_645
C15 H11 3.4895 no . 2_865
C15 H16B 3.3238 no . 1_455
C16 H8 3.4048 no . 1_645
C16 H10 3.0889 no . 1_645
C16 H10 3.3556 no . 2_865
C16 H11 3.1464 no . 2_865
C16 H15A 3.3041 no . 1_655
C16 H16A 3.5056 no . 2_955
C16 H16C 3.1422 no . 2_955
H1 Cl1 2.1573 no . 2_376
H1 C4 3.4019 no . 1_455
H1 H1A 3.3012 no . 2_476
H1 H3 3.0261 no . 2_376
H1 H4 3.4548 no . 1_455
H1 H6 3.4956 no . 2_376
H1A Cl1 2.6819 no . .
H1A O3 3.2324 no . 1_655
H1A N1 3.4966 no . 2_476
H1A C3 3.5604 no . 1_455
H1A H1 3.3012 no . 2_476
H1A H3 3.0974 no . 1_655
H1A H6 2.7344 no . 1_655
H2 Cl1 3.4423 no . 1_655
H2 O3 2.8931 no . 1_655
H2 H3 2.6368 no . 1_655
H2 H6 3.0412 no . 1_655
H2 H15B 3.0301 no . 1_365
H3 Cl1 2.08(5) no . .
H3 C1 3.50(5) no . 1_455
H3 C2 3.27(5) no . 1_455
H3 C5 3.28(5) no . 1_465
H3 H1 3.0261 no . 2_376
H3 H1A 3.0974 no . 1_455
H3 H2 2.6368 no . 1_455
H3 H4 3.3809 no . 1_365
H3 H4 3.4051 no . 1_465
H3 H5 2.7358 no . 1_465
H3 H5 3.5748 no . 2_376
H3 H6 3.38(8) no . 1_655
H3 H7 3.3060 no . 1_365
H3 H14 2.7655 no . 1_365
H4 Cl1 3.4811 no . 1_645
H4 O3 2.4921 no . 1_745
H4 N1 3.5572 no . 1_655
H4 C14 3.2631 no . 1_455
H4 H1 3.4548 no . 1_655
H4 H3 3.4051 no . 1_645
H4 H3 3.3809 no . 1_745
H4 H6 2.4298 no . 1_745
H4 H14 2.8960 no . 1_455
H5 Cl1 2.8589 no . 1_645
H5 Cl1 3.3216 no . 2_476
H5 O3 3.1957 no . 1_645
H5 H3 2.7358 no . 1_645
H5 H3 3.5748 no . 2_376
H5 H5 3.1753 no . 2_466
H5 H6 3.4940 no . 1_645
H5 H6 3.4834 no . 1_745
H5 H6 3.4137 no . 2_376
H6 Cl1 2.34(5) no . 1_455
H6 Cl1 3.38(5) no . .
H6 C1 3.45(4) no . 1_455
H6 C2 3.60(4) no . 1_455
H6 C4 3.31(4) no . 1_365
H6 H1 3.4956 no . 2_376
H6 H1A 2.7344 no . 1_455
H6 H2 3.0412 no . 1_455
H6 H3 3.38(8) no . 1_455
H6 H4 2.4298 no . 1_365
H6 H5 3.4834 no . 1_365
H6 H5 3.4940 no . 1_465
H6 H5 3.4137 no . 2_376
H6 H7 3.1442 no . 1_365
H6 H13 3.3518 no . 1_265
H6 H14 3.4307 no . 1_365
H7 O3 2.5714 no . 1_745
H7 N1 3.5065 no . 1_655
H7 C3 3.5304 no . 1_655
H7 C4 3.3081 no . 1_655
H7 C5 3.3164 no . 1_655
H7 C13 3.3917 no . 1_455
H7 C14 3.3993 no . 1_455
H7 H3 3.3060 no . 1_745
H7 H6 3.1442 no . 1_745
H8 C10 3.5949 no . 1_455
H8 C11 3.5158 no . 1_455
H8 C15 3.2580 no . 1_465
H8 C16 3.4048 no . 1_465
H8 H15A 2.5165 no . 1_465
H8 H15B 3.5740 no . 1_465
H8 H16A 3.1877 no . 1_365
H8 H16A 2.9350 no . 1_465
H8 H16C 3.5111 no . 1_465
H8 H16C 3.5487 no . 2_765
H10 O2 3.3479 no . 2_765
H10 C16 3.0889 no . 1_465
H10 C16 3.3556 no . 2_865
H10 H11 3.5338 no . 2_765
H10 H16A 2.4080 no . 1_465
H10 H16B 2.6846 no . 2_865
H10 H16C 2.9342 no . 1_465
H10 H16C 3.4032 no . 2_765
H10 H16C 3.1552 no . 2_865
H11 O2 2.6259 no . 2_865
H11 C10 3.3454 no . 2_765
H11 C11 3.0750 no . 2_765
H11 C11 3.5937 no . 2_865
H11 C12 3.5369 no . 2_765
H11 C12 3.5854 no . 2_865
H11 C15 3.4895 no . 2_865
H11 C16 3.1464 no . 2_865
H11 H10 3.5338 no . 2_765
H11 H11 3.1168 no . 2_765
H11 H11 2.9586 no . 2_865
H11 H16B 2.6410 no . 2_865
H11 H16C 3.0075 no . 2_865
H13 O1 2.8739 no . 1_645
H13 O3 3.1812 no . 1_845
H13 H6 3.3518 no . 1_845
H13 H15B 2.9255 no . 1_455
H13 H16B 3.2153 no . 1_455
H14 O3 2.5734 no . 1_745
H14 C4 3.1792 no . 1_655
H14 H3 2.7655 no . 1_745
H14 H4 2.8960 no . 1_655
H14 H6 3.4307 no . 1_745
H14 H15B 2.9148 no . 1_455
H15A O1 2.7778 no . 1_645
H15A C8 3.3745 no . 1_645
H15A C16 3.3041 no . 1_455
H15A H8 2.5165 no . 1_645
H15A H16A 3.0472 no . 1_455
H15A H16B 2.6970 no . 1_455
H15B O1 2.8881 no . 1_745
H15B C13 2.9475 no . 1_655
H15B C14 2.9464 no . 1_655
H15B H2 3.0301 no . 1_745
H15B H8 3.5740 no . 1_645
H15B H13 2.9255 no . 1_655
H15B H14 2.9148 no . 1_655
H16A O1 2.6192 no . 1_745
H16A C6 3.4398 no . 1_745
H16A C8 3.5196 no . 1_645
H16A C10 3.0356 no . 1_645
H16A C16 3.5056 no . 2_955
H16A H8 2.9350 no . 1_645
H16A H8 3.1877 no . 1_745
H16A H10 2.4080 no . 1_645
H16A H15A 3.0472 no . 1_655
H16A H16B 3.4257 no . 2_955
H16A H16C 2.9072 no . 2_955
H16B O1 3.4478 no . 1_745
H16B O2 3.0869 no . 1_655
H16B C10 3.3095 no . 2_865
H16B C11 3.2804 no . 2_865
H16B C12 2.9617 no . 1_655
H16B C13 3.0975 no . 1_655
H16B C15 3.3238 no . 1_655
H16B H10 2.6846 no . 2_865
H16B H11 2.6410 no . 2_865
H16B H13 3.2153 no . 1_655
H16B H15A 2.6970 no . 1_655
H16B H16A 3.4257 no . 2_955
H16B H16C 3.0529 no . 2_955
H16C C16 3.1422 no . 2_955
H16C H8 3.5111 no . 1_645
H16C H8 3.5487 no . 2_765
H16C H10 2.9342 no . 1_645
H16C H10 3.4032 no . 2_765
H16C H10 3.1552 no . 2_865
H16C H11 3.0075 no . 2_865
H16C H16A 2.9072 no . 2_955
H16C H16B 3.0529 no . 2_955
H16C H16C 3.1436 no . 2_855
H16C H16C 2.9321 no . 2_955

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 Cl1 . . . 3.179(3) 1.103 2.08(5) 173(4) no
O3 H6 Cl1 . . 1_455 3.203(3) 0.864 2.34(5) 175(4) no
N1 H1 Cl1 . . 2_376 3.034(3) 0.880 2.157 174.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
