# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef '- YTWang_r1.cif'

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

# 1. SUBMISSION DETAILS

_publ_contact_author             
# Name and address of author for correspondence
;
Wang, Yong-Tao
Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China

;
_publ_contact_author_phone       86-531-89000551
_publ_contact_author_fax         '86 531 89000551'
_publ_contact_author_email       ceswyt@yahoo.com.cn
_publ_requested_coeditor_name    ?
_publ_contact_letter             
;
Dear Sir or Madam:
Please consider this CIF as a supplmentary data for a manuscript
submitted to CrystEngComm.
March 25, 2011
;
#=================================================================

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?

_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?

_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?

_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?

_journal_techeditor_code         ?
_journal_techeditor_notes        ?

_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?

_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

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

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Nonlinear Optical and Ferroelectric Materials Based
on 1-Benzyl-2-phenyl-1H-benzimidazole Salts
;

loop_
_publ_author_name
_publ_author_address

'Yong-Tao Wang'
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
'Gui-Mei Tang'
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
'Chao He'
; Fujian Institute of Research on the Structure of Mater
Chinese Acaademy of Science
Fuzhou, 350002
P. R. China
;
'Shi-Chen Yan'
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
'Qi-Chao Hao'
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
;
Long Chen
;
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
'Xi-Fa Long'
; Fujian Institute of Research on the Structure of Mater
Chinese Acaademy of Science
Fuzhou, 350002
P. R. China
;
'Tian-Duo Li'
; Department of Engineering
Shandong Provincial Key Laboratory of Fine Chemicals
Shandong Polytechnic University
Jinan, 250353
P. R. China
;
'Seik-Weng Ng'
; Department of Chemistry
University of Malaya
Kuala Lumpur, 50603
Malaysia
;
_publ_contact_author_name        'Wang, Yong-Tao'

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

data_compound_2
#TrackingRef '- YTWang_r1.cif'

_database_code_depnum_ccdc_archive 'CCDC 795443'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_weight         347.37

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.707(3)
_cell_length_b                   8.886(5)
_cell_length_c                   9.503(5)
_cell_angle_alpha                71.733(5)
_cell_angle_beta                 79.378(9)
_cell_angle_gamma                84.199(9)
_cell_volume                     449.3(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1849
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.11

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             182
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2406
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1972
_reflns_number_gt                1480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+1.2299P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(6)
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     235
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.461(2) -0.5118(13) -1.1147(14) 0.127(4) Uani 1 1 d . . .
O2 O 0.515(3) -0.2740(14) -1.1539(12) 0.131(5) Uani 1 1 d . . .
O3 O 0.544(2) -0.4303(9) -0.9386(10) 0.097(3) Uani 1 1 d . . .
N1 N 0.5221(12) 0.0566(7) -0.8103(8) 0.0369(19) Uani 1 1 d . . .
N2 N 0.5982(13) -0.1521(9) -0.8913(8) 0.044(2) Uani 1 1 d . . .
H2 H 0.5460 -0.2044 -0.9217 0.052 Uiso 1 1 d R . .
N3 N 0.4931(18) -0.4044(12) -1.0673(12) 0.067(3) Uani 1 1 d . . .
C1 C 0.3940(18) 0.1782(10) -0.7433(10) 0.046(3) Uani 1 1 d . . .
H1A H 0.2302 0.1481 -0.7056 0.055 Uiso 1 1 calc R . .
H1B H 0.3905 0.2783 -0.8225 0.055 Uiso 1 1 calc R . .
C2 C 0.4956(16) 0.2044(10) -0.6179(10) 0.036(2) Uani 1 1 d . . .
C3 C 0.6930(16) 0.1117(12) -0.5594(11) 0.049(3) Uani 1 1 d . . .
H3A H 0.7657 0.0319 -0.5987 0.059 Uiso 1 1 calc R . .
C4 C 0.778(2) 0.1418(13) -0.4406(13) 0.058(3) Uani 1 1 d . . .
H4A H 0.9046 0.0795 -0.4003 0.070 Uiso 1 1 calc R . .
C5 C 0.6756(18) 0.2617(12) -0.3840(12) 0.054(3) Uani 1 1 d . . .
H5A H 0.7378 0.2843 -0.3094 0.065 Uiso 1 1 calc R . .
C6 C 0.474(2) 0.3508(12) -0.4402(13) 0.062(3) Uani 1 1 d . . .
H6A H 0.3955 0.4270 -0.3977 0.074 Uiso 1 1 calc R . .
C7 C 0.3963(17) 0.3235(11) -0.5580(11) 0.046(2) Uani 1 1 d . . .
H7A H 0.2716 0.3877 -0.5989 0.055 Uiso 1 1 calc R . .
C8 C 0.4531(14) -0.0863(9) -0.7933(9) 0.035(2) Uani 1 1 d . . .
C9 C 0.2596(14) -0.1720(9) -0.6792(10) 0.036(2) Uani 1 1 d . . .
C10 C 0.2343(17) -0.1751(11) -0.5292(11) 0.048(3) Uani 1 1 d . . .
H10A H 0.3374 -0.1207 -0.4993 0.058 Uiso 1 1 calc R . .
C11 C 0.051(2) -0.2613(12) -0.4241(13) 0.065(3) Uani 1 1 d . . .
H11A H 0.0311 -0.2617 -0.3246 0.078 Uiso 1 1 calc R . .
C12 C -0.0949(19) -0.3426(13) -0.4648(14) 0.062(3) Uani 1 1 d . . .
H12A H -0.2138 -0.3991 -0.3926 0.074 Uiso 1 1 calc R . .
C13 C -0.0747(17) -0.3453(11) -0.6101(13) 0.053(3) Uani 1 1 d . . .
H13A H -0.1794 -0.4019 -0.6362 0.064 Uiso 1 1 calc R . .
C14 C 0.1064(16) -0.2616(10) -0.7186(11) 0.045(2) Uani 1 1 d . . .
H14A H 0.1254 -0.2652 -0.8169 0.054 Uiso 1 1 calc R . .
C15 C 0.7765(16) -0.0464(10) -0.9730(9) 0.037(2) Uani 1 1 d . . .
C16 C 0.9748(17) -0.0629(13) -1.0773(11) 0.052(3) Uani 1 1 d . . .
H16A H 1.0028 -0.1517 -1.1109 0.062 Uiso 1 1 calc R . .
C17 C 1.129(2) 0.0617(14) -1.1285(13) 0.062(3) Uani 1 1 d . . .
H17A H 1.2650 0.0554 -1.1981 0.074 Uiso 1 1 calc R . .
C18 C 1.0869(19) 0.1979(13) -1.0778(13) 0.060(3) Uani 1 1 d . . .
H18A H 1.1956 0.2778 -1.1138 0.073 Uiso 1 1 calc R . .
C19 C 0.8801(19) 0.2139(14) -0.9728(11) 0.060(3) Uani 1 1 d . . .
H19A H 0.8473 0.3040 -0.9413 0.072 Uiso 1 1 calc R . .
C20 C 0.7300(15) 0.0871(9) -0.9200(9) 0.036(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.170(12) 0.100(7) 0.143(10) -0.060(7) -0.051(9) -0.035(8)
O2 0.214(15) 0.102(8) 0.080(7) -0.025(6) -0.033(8) -0.011(9)
O3 0.185(11) 0.042(4) 0.070(6) -0.021(4) -0.027(6) -0.001(5)
N1 0.044(5) 0.017(3) 0.048(4) 0.001(3) -0.022(4) -0.002(3)
N2 0.043(5) 0.050(5) 0.049(5) -0.029(4) -0.012(4) -0.001(4)
N3 0.082(8) 0.065(7) 0.063(7) -0.028(6) -0.013(6) -0.006(6)
C1 0.048(6) 0.025(5) 0.058(6) -0.007(4) -0.010(5) 0.011(4)
C2 0.030(4) 0.029(4) 0.046(5) -0.005(4) -0.009(4) 0.001(4)
C3 0.031(5) 0.060(6) 0.054(6) -0.019(5) -0.004(5) 0.005(5)
C4 0.053(7) 0.064(7) 0.066(7) -0.029(6) -0.020(5) 0.011(5)
C5 0.054(7) 0.057(7) 0.059(7) -0.025(6) -0.011(6) -0.014(6)
C6 0.065(8) 0.048(6) 0.067(8) -0.021(5) 0.009(6) -0.005(6)
C7 0.040(6) 0.042(5) 0.061(6) -0.026(5) -0.009(5) 0.003(5)
C8 0.032(5) 0.022(4) 0.043(5) 0.003(4) -0.014(4) 0.001(4)
C9 0.028(5) 0.035(5) 0.045(6) -0.010(4) -0.013(4) 0.003(4)
C10 0.045(6) 0.048(6) 0.056(6) -0.025(5) -0.005(5) -0.005(5)
C11 0.084(9) 0.046(6) 0.053(6) -0.010(5) 0.012(6) -0.011(6)
C12 0.044(7) 0.052(6) 0.075(9) -0.007(6) 0.011(6) -0.013(5)
C13 0.038(6) 0.039(6) 0.081(8) -0.013(5) -0.016(6) -0.006(5)
C14 0.034(5) 0.035(5) 0.061(6) -0.005(5) -0.012(5) -0.006(5)
C15 0.041(5) 0.033(5) 0.030(5) 0.005(4) -0.006(4) -0.012(4)
C16 0.044(6) 0.067(7) 0.042(6) -0.011(5) 0.002(5) -0.021(5)
C17 0.054(7) 0.078(8) 0.049(6) -0.018(6) -0.006(5) 0.005(6)
C18 0.050(7) 0.065(8) 0.059(7) -0.003(6) -0.002(6) -0.031(6)
C19 0.055(7) 0.080(8) 0.047(6) -0.015(6) -0.017(6) -0.010(6)
C20 0.040(5) 0.017(4) 0.041(5) 0.013(4) -0.009(4) -0.015(4)

_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 N3 1.217(12) . ?
O2 N3 1.196(13) . ?
O3 N3 1.255(12) . ?
N1 C8 1.321(10) . ?
N1 C20 1.414(12) . ?
N1 C1 1.485(11) . ?
N2 C8 1.361(11) . ?
N2 C15 1.402(11) . ?
N2 H2 0.7292 . ?
C1 C2 1.505(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.379(13) . ?
C2 C3 1.419(11) . ?
C3 C4 1.413(15) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(14) . ?
C4 H4A 0.9300 . ?
C5 C6 1.419(15) . ?
C5 H5A 0.9300 . ?
C6 C7 1.373(14) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.479(12) . ?
C9 C10 1.399(13) . ?
C9 C14 1.409(12) . ?
C10 C11 1.406(15) . ?
C10 H10A 0.9300 . ?
C11 C12 1.334(16) . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(15) . ?
C12 H12A 0.9300 . ?
C13 C14 1.402(14) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.389(13) . ?
C15 C20 1.411(13) . ?
C16 C17 1.394(15) . ?
C16 H16A 0.9300 . ?
C17 C18 1.420(15) . ?
C17 H17A 0.9300 . ?
C18 C19 1.425(16) . ?
C18 H18A 0.9300 . ?
C19 C20 1.392(13) . ?
C19 H19A 0.9300 . ?

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
C8 N1 C20 108.8(7) . . ?
C8 N1 C1 127.6(8) . . ?
C20 N1 C1 123.2(6) . . ?
C8 N2 C15 108.6(7) . . ?
C8 N2 H2 118.2 . . ?
C15 N2 H2 124.2 . . ?
O2 N3 O1 118.4(12) . . ?
O2 N3 O3 118.5(11) . . ?
O1 N3 O3 121.9(11) . . ?
N1 C1 C2 116.3(7) . . ?
N1 C1 H1A 108.2 . . ?
C2 C1 H1A 108.2 . . ?
N1 C1 H1B 108.2 . . ?
C2 C1 H1B 108.2 . . ?
H1A C1 H1B 107.4 . . ?
C7 C2 C3 118.3(9) . . ?
C7 C2 C1 119.4(7) . . ?
C3 C2 C1 122.3(8) . . ?
C4 C3 C2 119.3(9) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C5 C4 C3 120.9(10) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.4(10) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C7 C6 C5 119.3(11) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C6 C7 C2 122.6(9) . . ?
C6 C7 H7A 118.7 . . ?
C2 C7 H7A 118.7 . . ?
N1 C8 N2 110.1(7) . . ?
N1 C8 C9 126.7(8) . . ?
N2 C8 C9 123.1(7) . . ?
C10 C9 C14 118.6(8) . . ?
C10 C9 C8 121.2(8) . . ?
C14 C9 C8 120.0(8) . . ?
C9 C10 C11 119.1(10) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C12 C11 C10 121.0(12) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 121.9(11) . . ?
C11 C12 H12A 119.0 . . ?
C13 C12 H12A 119.0 . . ?
C12 C13 C14 119.0(10) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C13 C14 C9 120.2(10) . . ?
C13 C14 H14A 119.9 . . ?
C9 C14 H14A 119.9 . . ?
C16 C15 N2 130.8(9) . . ?
C16 C15 C20 123.1(9) . . ?
N2 C15 C20 105.9(8) . . ?
C15 C16 C17 116.0(10) . . ?
C15 C16 H16A 122.0 . . ?
C17 C16 H16A 122.0 . . ?
C16 C17 C18 122.2(10) . . ?
C16 C17 H17A 118.9 . . ?
C18 C17 H17A 118.9 . . ?
C17 C18 C19 121.0(10) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C20 C19 C18 116.2(11) . . ?
C20 C19 H19A 121.9 . . ?
C18 C19 H19A 121.9 . . ?
C19 C20 C15 121.4(9) . . ?
C19 C20 N1 132.0(9) . . ?
C15 C20 N1 106.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.076

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

data_compound_1
#TrackingRef '- YTWang_r1.cif'

_database_code_depnum_ccdc_archive 'CCDC 795444'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl N2 O4'
_chemical_formula_weight         384.81

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.7108(17)
_cell_length_b                   9.011(3)
_cell_length_c                   9.451(3)
_cell_angle_alpha                70.550(3)
_cell_angle_beta                 81.022(4)
_cell_angle_gamma                85.818(3)
_cell_volume                     452.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2060
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3954
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3193
_reflns_number_gt                2846
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     248
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.61437(8) 0.53212(6) 0.79825(6) 0.05288(17) Uani 1 1 d . . .
O1 O 0.7010(4) 0.4193(3) 0.7270(3) 0.0737(6) Uani 1 1 d . . .
O2 O 0.3683(4) 0.5083(3) 0.8538(3) 0.0943(8) Uani 1 1 d . . .
O3 O 0.7358(4) 0.5081(2) 0.9276(2) 0.0737(6) Uani 1 1 d . . .
O4 O 0.6507(5) 0.6889(3) 0.6989(3) 0.0910(8) Uani 1 1 d . . .
N1 N 0.7725(4) 0.7891(2) -0.0125(2) 0.0445(4) Uani 1 1 d . . .
N2 N 0.7051(3) 0.9922(2) 0.0649(2) 0.0419(4) Uani 1 1 d . . .
C1 C 0.9061(4) 1.0254(3) -0.0442(3) 0.0433(5) Uani 1 1 d . . .
C2 C 1.0583(5) 1.1523(3) -0.0976(3) 0.0531(6) Uani 1 1 d . . .
H2A H 1.0305 1.2398 -0.0655 0.064 Uiso 1 1 calc R . .
C3 C 1.2511(5) 1.1410(3) -0.2001(3) 0.0596(7) Uani 1 1 d . . .
H3A H 1.3558 1.2239 -0.2394 0.072 Uiso 1 1 calc R . .
C4 C 1.2957(5) 1.0096(4) -0.2476(3) 0.0586(7) Uani 1 1 d . . .
H4A H 1.4318 1.0059 -0.3148 0.070 Uiso 1 1 calc R . .
C5 C 1.1440(5) 0.8850(3) -0.1977(3) 0.0524(6) Uani 1 1 d . . .
H5A H 1.1708 0.7989 -0.2319 0.063 Uiso 1 1 calc R . .
C6 C 0.9481(4) 0.8953(3) -0.0931(3) 0.0431(5) Uani 1 1 d . . .
C7 C 0.6318(4) 0.8472(3) 0.0838(3) 0.0425(5) Uani 1 1 d . . .
C8 C 0.4370(4) 0.7625(3) 0.1933(3) 0.0439(5) Uani 1 1 d . . .
C9 C 0.2955(4) 0.6681(3) 0.1537(3) 0.0494(6) Uani 1 1 d . . .
H9A H 0.3223 0.6614 0.0563 0.059 Uiso 1 1 calc R . .
C10 C 0.1156(5) 0.5842(3) 0.2575(3) 0.0584(7) Uani 1 1 d . . .
H10A H 0.0182 0.5239 0.2291 0.070 Uiso 1 1 calc R . .
C11 C 0.0796(6) 0.5895(4) 0.4029(4) 0.0663(8) Uani 1 1 d . . .
H11A H -0.0423 0.5330 0.4729 0.080 Uiso 1 1 calc R . .
C12 C 0.2257(6) 0.6792(4) 0.4451(3) 0.0666(8) Uani 1 1 d . . .
H12A H 0.2019 0.6818 0.5438 0.080 Uiso 1 1 calc R . .
C13 C 0.4036(5) 0.7635(3) 0.3431(3) 0.0567(7) Uani 1 1 d . . .
H13A H 0.5026 0.8217 0.3729 0.068 Uiso 1 1 calc R . .
C14 C 0.5753(5) 1.1103(3) 0.1257(3) 0.0497(6) Uani 1 1 d . . .
H14A H 0.4129 1.0773 0.1626 0.060 Uiso 1 1 calc R . .
H14B H 0.5715 1.2096 0.0438 0.060 Uiso 1 1 calc R . .
C15 C 0.6801(4) 1.1365(3) 0.2521(3) 0.0433(5) Uani 1 1 d . . .
C16 C 0.5763(5) 1.2542(3) 0.3073(3) 0.0527(6) Uani 1 1 d . . .
H16A H 0.4504 1.3145 0.2642 0.063 Uiso 1 1 calc R . .
C17 C 0.6580(6) 1.2827(4) 0.4255(4) 0.0610(7) Uani 1 1 d . . .
H17A H 0.5865 1.3612 0.4623 0.073 Uiso 1 1 calc R . .
C18 C 0.8445(6) 1.1952(4) 0.4886(3) 0.0626(8) Uani 1 1 d . . .
H18A H 0.9005 1.2147 0.5679 0.075 Uiso 1 1 calc R . .
C19 C 0.9487(6) 1.0790(4) 0.4349(3) 0.0643(7) Uani 1 1 d . . .
H19A H 1.0752 1.0197 0.4781 0.077 Uiso 1 1 calc R . .
C20 C 0.8664(5) 1.0493(3) 0.3160(3) 0.0573(7) Uani 1 1 d . . .
H20A H 0.9379 0.9702 0.2800 0.069 Uiso 1 1 calc R . .
H1 H 0.740(4) 0.697(3) -0.031(3) 0.047(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0643(4) 0.0443(3) 0.0537(3) -0.0220(3) -0.0046(3) -0.0041(3)
O1 0.0886(15) 0.0695(14) 0.0759(14) -0.0448(12) -0.0024(12) -0.0009(11)
O2 0.0607(14) 0.111(2) 0.126(2) -0.0635(19) 0.0068(13) -0.0120(12)
O3 0.1047(17) 0.0542(12) 0.0747(14) -0.0300(11) -0.0336(12) 0.0076(11)
O4 0.133(2) 0.0494(12) 0.0793(15) -0.0061(11) -0.0120(15) -0.0100(12)
N1 0.0534(12) 0.0406(11) 0.0437(10) -0.0179(9) -0.0092(9) -0.0029(9)
N2 0.0440(10) 0.0420(11) 0.0439(10) -0.0182(9) -0.0097(8) -0.0002(8)
C1 0.0465(13) 0.0422(13) 0.0438(12) -0.0146(10) -0.0119(10) -0.0039(10)
C2 0.0596(15) 0.0454(14) 0.0584(16) -0.0169(12) -0.0177(13) -0.0060(11)
C3 0.0598(17) 0.0587(18) 0.0564(15) -0.0115(13) -0.0051(13) -0.0184(13)
C4 0.0507(15) 0.0705(19) 0.0487(14) -0.0140(13) 0.0014(12) -0.0084(12)
C5 0.0580(15) 0.0554(15) 0.0449(13) -0.0193(12) -0.0045(11) 0.0002(12)
C6 0.0462(12) 0.0433(13) 0.0410(12) -0.0132(10) -0.0093(10) -0.0050(10)
C7 0.0472(13) 0.0425(13) 0.0420(12) -0.0174(11) -0.0109(10) -0.0008(10)
C8 0.0453(13) 0.0423(13) 0.0439(12) -0.0135(11) -0.0079(10) 0.0011(10)
C9 0.0488(14) 0.0537(15) 0.0468(13) -0.0171(12) -0.0064(11) -0.0053(11)
C10 0.0571(15) 0.0511(16) 0.0660(16) -0.0156(13) -0.0091(13) -0.0102(12)
C11 0.0622(17) 0.0659(19) 0.0629(18) -0.0171(15) 0.0115(14) -0.0138(14)
C12 0.078(2) 0.0690(19) 0.0501(14) -0.0216(14) 0.0079(14) -0.0086(15)
C13 0.0657(17) 0.0598(17) 0.0501(13) -0.0254(13) -0.0055(12) -0.0076(13)
C14 0.0561(14) 0.0437(13) 0.0549(14) -0.0223(12) -0.0131(12) 0.0050(11)
C15 0.0456(13) 0.0416(13) 0.0445(11) -0.0166(10) -0.0045(10) -0.0042(9)
C16 0.0583(15) 0.0456(14) 0.0574(15) -0.0220(12) -0.0062(12) 0.0007(11)
C17 0.0742(18) 0.0553(17) 0.0617(16) -0.0342(15) 0.0034(14) -0.0092(14)
C18 0.080(2) 0.0664(18) 0.0501(15) -0.0272(14) -0.0077(14) -0.0212(15)
C19 0.0721(18) 0.071(2) 0.0572(16) -0.0261(15) -0.0194(14) -0.0023(14)
C20 0.0615(16) 0.0591(17) 0.0609(15) -0.0305(14) -0.0165(13) 0.0062(13)

_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
Cl1 O1 1.4180(18) . ?
Cl1 O4 1.421(2) . ?
Cl1 O2 1.426(2) . ?
Cl1 O3 1.445(2) . ?
N1 C7 1.333(3) . ?
N1 C6 1.385(3) . ?
N1 H1 0.94(3) . ?
N2 C7 1.347(3) . ?
N2 C1 1.395(3) . ?
N2 C14 1.473(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.393(4) . ?
C2 C3 1.370(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5A 0.9300 . ?
C7 C8 1.459(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.376(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.508(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.370(4) . ?
C15 C16 1.389(3) . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.370(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.392(4) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cl1 O4 112.11(14) . . ?
O1 Cl1 O2 109.52(14) . . ?
O4 Cl1 O2 110.16(18) . . ?
O1 Cl1 O3 108.89(14) . . ?
O4 Cl1 O3 108.78(15) . . ?
O2 Cl1 O3 107.24(15) . . ?
C7 N1 C6 109.65(18) . . ?
C7 N1 H1 123.2(15) . . ?
C6 N1 H1 126.5(16) . . ?
C7 N2 C1 108.89(18) . . ?
C7 N2 C14 126.6(2) . . ?
C1 N2 C14 123.59(19) . . ?
C6 C1 N2 106.27(18) . . ?
C6 C1 C2 121.6(2) . . ?
N2 C1 C2 132.0(2) . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 H2A 121.9 . . ?
C1 C2 H2A 121.9 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3A 118.8 . . ?
C4 C3 H3A 118.8 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 C6 116.2(2) . . ?
C4 C5 H5A 121.9 . . ?
C6 C5 H5A 121.9 . . ?
N1 C6 C1 106.59(18) . . ?
N1 C6 C5 131.5(2) . . ?
C1 C6 C5 121.8(2) . . ?
N1 C7 N2 108.5(2) . . ?
N1 C7 C8 124.4(2) . . ?
N2 C7 C8 127.0(2) . . ?
C9 C8 C13 119.0(2) . . ?
C9 C8 C7 120.0(2) . . ?
C13 C8 C7 120.8(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13A 120.0 . . ?
C8 C13 H13A 120.0 . . ?
N2 C14 C15 114.2(2) . . ?
N2 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 119.1(2) . . ?
C20 C15 C14 123.7(2) . . ?
C16 C15 C14 117.2(2) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C15 C20 C19 119.9(2) . . ?
C15 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034

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

data_compound_3
#TrackingRef '- YTWang_r1.cif'

_database_code_depnum_ccdc_archive 'CCDC 795445'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl N2 O'
_chemical_formula_weight         338.82

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.441(4)
_cell_length_b                   8.892(6)
_cell_length_c                   9.554(7)
_cell_angle_alpha                74.542(8)
_cell_angle_beta                 82.346(8)
_cell_angle_gamma                76.224(8)
_cell_volume                     431.5(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2367
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             178
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9555
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3741
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3005
_reflns_number_gt                2817
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     229
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.2376(5) 0.3027(3) 0.0587(2) 0.0665(5) Uani 1 1 d . . .
Cl1 Cl 0.66409(11) 0.45710(8) 0.10162(7) 0.0682(2) Uani 1 1 d . . .
N1 N 0.4735(3) 0.1978(2) 0.58612(16) 0.0377(3) Uani 1 1 d . . .
N2 N 0.3359(3) 0.26975(19) 0.78897(17) 0.0376(3) Uani 1 1 d . . .
C1 C 0.2512(4) 0.3125(2) 0.5583(2) 0.0390(4) Uani 1 1 d . . .
C2 C 0.1167(5) 0.3751(3) 0.4331(2) 0.0477(5) Uani 1 1 d . . .
H2A H 0.1767 0.3462 0.3461 0.057 Uiso 1 1 calc R . .
C3 C -0.1084(5) 0.4814(3) 0.4460(3) 0.0549(6) Uani 1 1 d . . .
H3A H -0.2038 0.5256 0.3654 0.066 Uiso 1 1 calc R . .
C4 C -0.1989(5) 0.5255(3) 0.5763(3) 0.0543(6) Uani 1 1 d . . .
H4A H -0.3527 0.5981 0.5794 0.065 Uiso 1 1 calc R . .
C5 C -0.0677(4) 0.4651(2) 0.7010(2) 0.0453(5) Uani 1 1 d . . .
H5A H -0.1291 0.4942 0.7877 0.054 Uiso 1 1 calc R . .
C6 C 0.1618(4) 0.3578(2) 0.6881(2) 0.0383(4) Uani 1 1 d . . .
C7 C 0.5183(4) 0.1727(2) 0.72735(19) 0.0359(4) Uani 1 1 d . . .
C8 C 0.7262(4) 0.0565(2) 0.80479(19) 0.0378(4) Uani 1 1 d . . .
C9 C 0.8435(4) 0.0990(2) 0.9055(2) 0.0402(4) Uani 1 1 d . . .
H9A H 0.7891 0.1999 0.9237 0.048 Uiso 1 1 calc R . .
C10 C 1.0414(4) -0.0096(3) 0.9782(2) 0.0470(5) Uani 1 1 d . . .
H10A H 1.1217 0.0197 1.0438 0.056 Uiso 1 1 calc R . .
C11 C 1.1201(4) -0.1599(3) 0.9547(2) 0.0502(5) Uani 1 1 d . . .
H11A H 1.2548 -0.2313 1.0029 0.060 Uiso 1 1 calc R . .
C12 C 0.9987(5) -0.2054(3) 0.8590(3) 0.0539(6) Uani 1 1 d . . .
H12A H 1.0489 -0.3084 0.8454 0.065 Uiso 1 1 calc R . .
C13 C 0.8026(4) -0.0981(2) 0.7836(2) 0.0466(5) Uani 1 1 d . . .
H13A H 0.7221 -0.1288 0.7191 0.056 Uiso 1 1 calc R . .
C14 C 0.6340(4) 0.1302(3) 0.4717(2) 0.0415(4) Uani 1 1 d . . .
H14A H 0.8003 0.0787 0.5066 0.050 Uiso 1 1 calc R . .
H14B H 0.6555 0.2163 0.3871 0.050 Uiso 1 1 calc R . .
C15 C 0.5246(4) 0.0099(2) 0.42669(19) 0.0375(4) Uani 1 1 d . . .
C16 C 0.6249(4) -0.0296(3) 0.2960(2) 0.0480(5) Uani 1 1 d . . .
H16A H 0.7520 0.0181 0.2400 0.058 Uiso 1 1 calc R . .
C17 C 0.5346(5) -0.1403(3) 0.2497(2) 0.0542(6) Uani 1 1 d . . .
H17A H 0.6042 -0.1680 0.1634 0.065 Uiso 1 1 calc R . .
C18 C 0.3439(5) -0.2094(3) 0.3300(3) 0.0521(5) Uani 1 1 d . . .
H18A H 0.2832 -0.2825 0.2976 0.063 Uiso 1 1 calc R . .
C19 C 0.2418(4) -0.1698(3) 0.4596(3) 0.0493(5) Uani 1 1 d . . .
H19A H 0.1121 -0.2161 0.5142 0.059 Uiso 1 1 calc R . .
C20 C 0.3340(4) -0.0604(2) 0.5081(2) 0.0424(4) Uani 1 1 d . . .
H20A H 0.2668 -0.0348 0.5956 0.051 Uiso 1 1 calc R . .
H1WA H 0.297(8) 0.361(5) 0.078(4) 0.087(12) Uiso 1 1 d . . .
H2 H 0.310(6) 0.276(4) 0.885(4) 0.073(9) Uiso 1 1 d . . .
H1WB H 0.079(9) 0.364(5) 0.072(4) 0.093(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0592(13) 0.0947(14) 0.0561(9) -0.0385(10) -0.0065(8) -0.0125(12)
Cl1 0.0552(4) 0.0874(5) 0.0708(4) -0.0336(3) -0.0039(3) -0.0164(3)
N1 0.0352(8) 0.0438(8) 0.0347(7) -0.0105(6) -0.0047(6) -0.0077(7)
N2 0.0331(8) 0.0439(9) 0.0365(7) -0.0120(6) -0.0047(6) -0.0058(7)
C1 0.0380(10) 0.0396(9) 0.0407(9) -0.0096(8) -0.0059(7) -0.0095(8)
C2 0.0568(14) 0.0469(11) 0.0392(10) -0.0067(8) -0.0142(9) -0.0093(10)
C3 0.0610(16) 0.0478(11) 0.0548(12) -0.0057(10) -0.0254(11) -0.0051(11)
C4 0.0478(13) 0.0425(11) 0.0702(14) -0.0128(10) -0.0195(11) 0.0022(10)
C5 0.0402(12) 0.0425(10) 0.0537(11) -0.0147(9) -0.0041(9) -0.0061(9)
C6 0.0357(10) 0.0386(10) 0.0415(9) -0.0077(8) -0.0068(7) -0.0097(8)
C7 0.0320(10) 0.0419(10) 0.0375(9) -0.0100(7) -0.0043(7) -0.0133(8)
C8 0.0316(10) 0.0462(10) 0.0357(8) -0.0065(8) -0.0044(7) -0.0111(8)
C9 0.0415(11) 0.0438(10) 0.0369(9) -0.0084(7) -0.0047(7) -0.0126(9)
C10 0.0424(12) 0.0608(13) 0.0395(9) -0.0074(9) -0.0110(8) -0.0153(10)
C11 0.0411(12) 0.0566(12) 0.0459(10) -0.0040(9) -0.0119(9) -0.0016(10)
C12 0.0560(15) 0.0464(12) 0.0569(12) -0.0109(10) -0.0130(11) -0.0033(10)
C13 0.0467(13) 0.0479(11) 0.0495(10) -0.0141(9) -0.0124(9) -0.0110(10)
C14 0.0348(10) 0.0547(11) 0.0369(9) -0.0140(8) 0.0004(7) -0.0117(9)
C15 0.0332(10) 0.0432(10) 0.0341(8) -0.0086(7) -0.0075(7) -0.0021(8)
C16 0.0466(12) 0.0599(12) 0.0373(9) -0.0128(9) -0.0024(8) -0.0101(10)
C17 0.0589(14) 0.0634(14) 0.0430(10) -0.0205(10) -0.0107(10) -0.0061(12)
C18 0.0558(14) 0.0476(11) 0.0572(12) -0.0166(10) -0.0228(10) -0.0047(10)
C19 0.0386(12) 0.0480(11) 0.0631(13) -0.0129(10) -0.0087(9) -0.0107(9)
C20 0.0337(10) 0.0500(11) 0.0441(10) -0.0128(9) -0.0038(8) -0.0076(9)

_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 H1WA 0.74(4) . ?
O1 H1WB 0.91(5) . ?
N1 C7 1.353(2) . ?
N1 C1 1.388(3) . ?
N1 C14 1.471(2) . ?
N2 C7 1.336(3) . ?
N2 C6 1.388(3) . ?
N2 H2 0.92(3) . ?
C1 C6 1.396(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.371(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.397(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5A 0.9300 . ?
C7 C8 1.467(3) . ?
C8 C9 1.396(3) . ?
C8 C13 1.399(3) . ?
C9 C10 1.386(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.386(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.517(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.381(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.386(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.395(3) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

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
H1WA O1 H1WB 91(4) . . ?
C7 N1 C1 108.67(15) . . ?
C7 N1 C14 128.46(18) . . ?
C1 N1 C14 122.70(15) . . ?
C7 N2 C6 109.65(16) . . ?
C7 N2 H2 129(2) . . ?
C6 N2 H2 121(2) . . ?
N1 C1 C6 106.84(16) . . ?
N1 C1 C2 131.42(18) . . ?
C6 C1 C2 121.7(2) . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 H2A 121.9 . . ?
C1 C2 H2A 121.9 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 115.7(2) . . ?
C4 C5 H5A 122.2 . . ?
C6 C5 H5A 122.2 . . ?
N2 C6 C5 131.82(19) . . ?
N2 C6 C1 106.17(17) . . ?
C5 C6 C1 121.92(18) . . ?
N2 C7 N1 108.65(17) . . ?
N2 C7 C8 124.25(16) . . ?
N1 C7 C8 127.08(17) . . ?
C9 C8 C13 119.35(18) . . ?
C9 C8 C7 119.40(18) . . ?
C13 C8 C7 121.21(17) . . ?
C10 C9 C8 119.74(19) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 120.75(18) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C12 C13 C8 119.84(19) . . ?
C12 C13 H13A 120.1 . . ?
C8 C13 H13A 120.1 . . ?
N1 C14 C15 113.06(16) . . ?
N1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C20 C15 C16 119.50(19) . . ?
C20 C15 C14 123.39(17) . . ?
C16 C15 C14 117.11(18) . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C15 C20 C19 120.28(19) . . ?
C15 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037

# End of files